US20040010858A1 - Hydrophilically modified polyisocyanates and polyurethanes for crease-proofing textiles containing cellulose - Google Patents
Hydrophilically modified polyisocyanates and polyurethanes for crease-proofing textiles containing cellulose Download PDFInfo
- Publication number
- US20040010858A1 US20040010858A1 US10/416,336 US41633603A US2004010858A1 US 20040010858 A1 US20040010858 A1 US 20040010858A1 US 41633603 A US41633603 A US 41633603A US 2004010858 A1 US2004010858 A1 US 2004010858A1
- Authority
- US
- United States
- Prior art keywords
- weight
- hydrophilic modified
- polyurethane
- new
- bactericides
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 94
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 94
- 239000004753 textile Substances 0.000 title claims abstract description 70
- 239000004814 polyurethane Substances 0.000 title claims abstract description 66
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 66
- 239000001913 cellulose Substances 0.000 title description 2
- 229920002678 cellulose Polymers 0.000 title description 2
- 238000004855 creaseproofing Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000001035 drying Methods 0.000 claims abstract description 7
- -1 softeners Substances 0.000 claims description 32
- 239000000654 additive Substances 0.000 claims description 25
- 239000000975 dye Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002736 nonionic surfactant Substances 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 239000004615 ingredient Substances 0.000 claims description 18
- 230000000844 anti-bacterial effect Effects 0.000 claims description 17
- 239000003899 bactericide agent Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000003599 detergent Substances 0.000 claims description 17
- 239000007844 bleaching agent Substances 0.000 claims description 16
- 239000003093 cationic surfactant Substances 0.000 claims description 16
- 230000007797 corrosion Effects 0.000 claims description 16
- 238000005260 corrosion Methods 0.000 claims description 16
- 239000002689 soil Substances 0.000 claims description 16
- 239000003112 inhibitor Substances 0.000 claims description 15
- 229920001296 polysiloxane Polymers 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 238000010409 ironing Methods 0.000 claims description 12
- 239000003945 anionic surfactant Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 239000000314 lubricant Substances 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 239000012190 activator Substances 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 239000008139 complexing agent Substances 0.000 claims description 8
- 238000004900 laundering Methods 0.000 claims description 8
- 239000002304 perfume Substances 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 8
- 238000005507 spraying Methods 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 8
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 239000000080 wetting agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 5
- 239000002998 adhesive polymer Substances 0.000 claims description 4
- 239000007884 disintegrant Substances 0.000 claims description 4
- 238000004090 dissolution Methods 0.000 claims description 4
- 239000003752 hydrotrope Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 239000000178 monomer Substances 0.000 description 26
- 125000005442 diisocyanate group Chemical group 0.000 description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 description 17
- 229920000570 polyether Polymers 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 125000003010 ionic group Chemical group 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 150000003839 salts Chemical group 0.000 description 8
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 150000002596 lactones Chemical class 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 230000037303 wrinkles Effects 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001414 amino alcohols Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000002979 fabric softener Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 0 [9*]N([10*])[11*]O Chemical compound [9*]N([10*])[11*]O 0.000 description 2
- 229940048053 acrylate Drugs 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical class OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- LPTIRUACFKQDHZ-UHFFFAOYSA-N hexadecyl sulfate;hydron Chemical compound CCCCCCCCCCCCCCCCOS(O)(=O)=O LPTIRUACFKQDHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 150000005621 tetraalkylammonium salts Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 1
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- CEGRHPCDLKAHJD-UHFFFAOYSA-N 1,1,1-propanetricarboxylic acid Chemical compound CCC(C(O)=O)(C(O)=O)C(O)=O CEGRHPCDLKAHJD-UHFFFAOYSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- ODKSRULWLOLNJQ-UHFFFAOYSA-N 1,2-diisocyanatocyclohexane Chemical compound O=C=NC1CCCCC1N=C=O ODKSRULWLOLNJQ-UHFFFAOYSA-N 0.000 description 1
- PFUKECZPRROVOD-UHFFFAOYSA-N 1,3,5-triisocyanato-2-methylbenzene Chemical compound CC1=C(N=C=O)C=C(N=C=O)C=C1N=C=O PFUKECZPRROVOD-UHFFFAOYSA-N 0.000 description 1
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- JMFCAIUTSABFDU-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O JMFCAIUTSABFDU-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- JPIGSMKDJQPHJC-UHFFFAOYSA-N 1-(2-aminoethoxy)ethanol Chemical compound CC(O)OCCN JPIGSMKDJQPHJC-UHFFFAOYSA-N 0.000 description 1
- FNGREQBHSNEPKP-UHFFFAOYSA-N 1-(3,4-dihydrooxazin-2-yl)propan-2-ol Chemical compound CC(O)CN1CCC=CO1 FNGREQBHSNEPKP-UHFFFAOYSA-N 0.000 description 1
- MHKUWCCXUOVTMU-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-oxazol-2-yl)propan-2-ol Chemical compound CC(O)CC1=NCCO1 MHKUWCCXUOVTMU-UHFFFAOYSA-N 0.000 description 1
- PCAFNJDUSMKKHJ-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound CC(O)CN1CCN(C)CC1 PCAFNJDUSMKKHJ-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- KSYQGOYOIKQFNA-UHFFFAOYSA-N 1-benzyl-3-methylbenzene Chemical compound CC1=CC=CC(CC=2C=CC=CC=2)=C1 KSYQGOYOIKQFNA-UHFFFAOYSA-N 0.000 description 1
- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- SWZKXIPDGAAYKE-UHFFFAOYSA-N 1-morpholin-4-ylpropan-2-amine Chemical compound CC(N)CN1CCOCC1 SWZKXIPDGAAYKE-UHFFFAOYSA-N 0.000 description 1
- YAXQOLYGKLGQKA-UHFFFAOYSA-N 1-morpholin-4-ylpropan-2-ol Chemical compound CC(O)CN1CCOCC1 YAXQOLYGKLGQKA-UHFFFAOYSA-N 0.000 description 1
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 description 1
- ZGZHNQPTNCGKHS-UHFFFAOYSA-N 1-n,1-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)N ZGZHNQPTNCGKHS-UHFFFAOYSA-N 0.000 description 1
- RRQHLOZQFPWDCA-UHFFFAOYSA-N 1-n,1-n-dimethylpropane-1,2-diamine Chemical compound CC(N)CN(C)C RRQHLOZQFPWDCA-UHFFFAOYSA-N 0.000 description 1
- ZFDABCDCTKLGOK-UHFFFAOYSA-N 1-piperidin-1-ylpropan-2-amine Chemical compound CC(N)CN1CCCCC1 ZFDABCDCTKLGOK-UHFFFAOYSA-N 0.000 description 1
- UCASFSAKVJTSET-UHFFFAOYSA-N 1-piperidin-1-ylpropan-2-ol Chemical compound CC(O)CN1CCCCC1 UCASFSAKVJTSET-UHFFFAOYSA-N 0.000 description 1
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 1
- YIWSGJJFUXYOJI-UHFFFAOYSA-N 2,3-dihydroxypropyl(ethoxy)phosphinic acid Chemical compound CCOP(O)(=O)CC(O)CO YIWSGJJFUXYOJI-UHFFFAOYSA-N 0.000 description 1
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 1
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 1
- PQHYOGIRXOKOEJ-UHFFFAOYSA-N 2-(1,2-dicarboxyethylamino)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NC(C(O)=O)CC(O)=O PQHYOGIRXOKOEJ-UHFFFAOYSA-N 0.000 description 1
- IVGRSQBDVIJNDA-UHFFFAOYSA-N 2-(2-aminoethylamino)ethanesulfonic acid Chemical compound NCCNCCS(O)(=O)=O IVGRSQBDVIJNDA-UHFFFAOYSA-N 0.000 description 1
- IKTKBPBOEUDORD-UHFFFAOYSA-N 2-(3,4-dihydrooxazin-2-yl)ethanol Chemical compound OCCN1CCC=CO1 IKTKBPBOEUDORD-UHFFFAOYSA-N 0.000 description 1
- PAWVJRPRVYDHLQ-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)ethanol Chemical compound OCCC1=NCCO1 PAWVJRPRVYDHLQ-UHFFFAOYSA-N 0.000 description 1
- QHTUMQYGZQYEOZ-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethanol Chemical compound CN1CCN(CCO)CC1 QHTUMQYGZQYEOZ-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- NDLNTMNRNCENRZ-UHFFFAOYSA-N 2-[2-hydroxyethyl(octadecyl)amino]ethanol Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)CCO NDLNTMNRNCENRZ-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 1
- IYBOGQYZTIIPNI-UHFFFAOYSA-N 2-methylhexano-6-lactone Chemical compound CC1CCCCOC1=O IYBOGQYZTIIPNI-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- BOLMDIXLULGTBD-UHFFFAOYSA-N 3,4-dihydro-2h-oxazine Chemical group C1CC=CON1 BOLMDIXLULGTBD-UHFFFAOYSA-N 0.000 description 1
- NNLRDVBAHRQMHK-UHFFFAOYSA-N 3-(2-aminoethylamino)propanoic acid Chemical compound NCCNCCC(O)=O NNLRDVBAHRQMHK-UHFFFAOYSA-N 0.000 description 1
- YQYKHRLORGCFJR-UHFFFAOYSA-N 3-(3,4-dihydrooxazin-2-yl)propan-1-ol Chemical compound OCCCN1CCC=CO1 YQYKHRLORGCFJR-UHFFFAOYSA-N 0.000 description 1
- VEERNCWDIVHRAJ-UHFFFAOYSA-N 3-(4,5-dihydro-1,3-oxazol-2-yl)propan-1-ol Chemical compound OCCCC1=NCCO1 VEERNCWDIVHRAJ-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- UWRBFYBQPCJRRL-UHFFFAOYSA-N 3-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)CCN(CC(O)=O)CC(O)=O UWRBFYBQPCJRRL-UHFFFAOYSA-N 0.000 description 1
- WACQLQIAUWURGA-UHFFFAOYSA-N 3-hydroxy-2,2-bis(hydroxymethyl)propanoic acid Chemical compound OCC(CO)(CO)C(O)=O WACQLQIAUWURGA-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- ULMZOZMSDIOZAF-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)propanoic acid Chemical compound OCC(CO)C(O)=O ULMZOZMSDIOZAF-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GSFOUKVQYFLTRA-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)butan-1-ol Chemical compound CN1CCN(CCCCO)CC1 GSFOUKVQYFLTRA-UHFFFAOYSA-N 0.000 description 1
- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical compound NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 229940006015 4-hydroxybutyric acid Drugs 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical compound OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- CVGYTOLNWAMTRJ-UHFFFAOYSA-N N=C=O.N=C=O.CCCCC(C)C(C)(C)C Chemical compound N=C=O.N=C=O.CCCCC(C)C(C)(C)C CVGYTOLNWAMTRJ-UHFFFAOYSA-N 0.000 description 1
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000805 Polyaspartic acid Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229940040563 agaric acid Drugs 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical class CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000002752 cationic softener Substances 0.000 description 1
- 229940080284 cetyl sulfate Drugs 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical class NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 125000004395 glucoside group Chemical group 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical class CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ULDIVZQLPBUHAG-UHFFFAOYSA-N n',n',2,2-tetramethylpropane-1,3-diamine Chemical compound CN(C)CC(C)(C)CN ULDIVZQLPBUHAG-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 description 1
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 229910021527 natrosilite Inorganic materials 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical class CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- URLJMZWTXZTZRR-UHFFFAOYSA-N sodium myristyl sulfate Chemical compound CCCCCCCCCCCCCCOS(O)(=O)=O URLJMZWTXZTZRR-UHFFFAOYSA-N 0.000 description 1
- 229950005425 sodium myristyl sulfate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 229910003319 β-Na2Si2O5 Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3726—Polyurethanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/568—Reaction products of isocyanates with polyethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/572—Reaction products of isocyanates with polyesters or polyesteramides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
Definitions
- This invention relates to processes for wrinkleproofing cellulosic textiles, wrinkleproofing finishes comprising hydrophilic modified polyisocyanates and/or polyurethanes, the use of the finishes and of the polyisocyanates and polyurethanes, and also textile treatments, solid and liquid laundry detergents and laundry refreshers comprising same.
- Cellulosic textiles are given easy care properties by treatment with condensation products of urea, glyoxal and formaldehyde, for example.
- the finish is applied during the manufacture of textile materials. Softening compounds are frequently further applied with the finish.
- finished textiles are less wrinkled and creased, easier to iron and softer and smoother after laundering compared with untreated cellulose textiles.
- WO 92/01773 discloses the use of microemulsified aminosiloxanes in fabric conditioners to reduce wrinkling and creasing during the laundering process. In addition, the use of aminosiloxanes is said to facilitate ironing.
- WO 98/4772 discloses a process for pretreating textile materials by applying a mixture of a polycarboxylic acid and a cationic softener to the textile materials. Wrinkle control is obtained as a result.
- EP-A 0 300 525 discloses fabric conditioners based on crosslinkable amino-functionalized silicones that impart wrinkle control or an easy-iron effect to textiles treated therewith.
- WO 99/55953 discloses fabric wrinkle control compositions. They comprise lubricants, shape retention polymers, lithium salts and optionally further ingredients such as softeners, ionic and nonionic surfactants, odor control agents and bactericides. The formulation is preferably applied to the textile material by spraying.
- EP-A 0 978 556 describes a mixture of a softener and a crosslinker component having cationic properties as a fabric wrinkle and crease control composition and also a method of wrinkleproofing textiles.
- the invention also provides a wrinkleproofing finish for cellulosic textiles that comprises hydrophilic modified polyisocyanates and polyurethanes.
- the finish of the invention may include (A) one or more hydrophilic modified polyisocyanates.
- hydrophilic modified polyisocyanates to be used according to this invention are based on customary diisocyanates and/or customary higher functional polyisocyanates having an average NCO functionality of from 2.0 to 4.5. These components can be present alone or mixed.
- customary diisocyanates are aliphatic diisocyanates such as tetramethylene diisocyanate, hexamethylene diisocyanate (1,6-diisocyanatohexane), octamethylene diisocyanate, decamethylene diisocyanate, dodecamethylene diisocyanate, tetradecamethylene diisocyanate, trimethylhexane diisocyanate or tetramethylhexane diisocyanate, cycloaliphatic diisocyanates such as 1,4-, 1,3- or 1,2-diisocyanatocyclohexane, 4,4′-di(isocyanatocyclohexyl)methane, 1-isocyanato-3,3,5-trimethyl-5-(isocyanatomethyl)cyclohexane (isophorone diisocyanate) or 2,4- or 2,6-diisocyanato-1-methylcyclohex
- Suitable customary higher functional polyisocyanates are for example triisocyanates such as 2,4,6-triisocyanatotoluene or 2,4,4′-triisocyanatodiphenyl ether or the mixtures of di-, tri- and higher polyisocyanates which are obtained by phosgenation of corresponding aniline/formaldehyde condensates and are methylene-bridged polyphenyl polyisocyanates.
- the present isocyanurates are in particular simple trisisocyanatoalkyl or triisocyanatocycloalkyl isocyanurates which are cyclic trimers of the diisocyanates, or mixtures with their higher homologs having more than one isocyanurate ring.
- the isocyanato-isocyanurates generally have an NCO content of from 10 to 30% by weight, in particular of from 15 to 25% by weight, and an average NCO functionality of from 2.6 to 4.5.
- Uretidione-group-containing polyisocyanates having aliphatically and/or cycloaliphatically bound isocyanate groups, preferably derived from hexamethylene diisocyanate or isophorone diisocyanate.
- Uretidiones are cyclic dimerization products of two NCO groups.
- Biuret-group-containing polyisocyanates having aliphatically bound isocyanate groups, in particular tris(6-isocyanatohexyl) biuret or its mixtures with its higher homologs.
- These biuret-group-containing polyisocyanates generally have an NCO content of from 18 to 25% by weight and an average NCO functionality of from 3 to 4.5.
- Urethane- and/or allophanate-group-containing polyisocyanates with aliphatically or cycloaliphatically bound isocyanate groups as obtainable for example by reacting excess amounts of hexamethylene diisocyanate or isophorone diisocyanate with simple polyhydric alcohols such as trimethylolpropane, glycerol, 1,2-dihydroxypropane or mixtures thereof.
- These urethano- and/or allophanato-containing polyisocyanates generally have an NCO content of from 12 to 20% by weight and an average NCO functionality of from 2.5 to 3.
- Oxadiazinetrione-group-containing polyisocyanates preferably derived from hexamethylene diisocyanate or isophorone diisocyanate. Such oxadiazinetriono-containing polyisocyanates are preparable from diisocyanate and carbon dioxide.
- the described diisocyanates and/or higher functionalized polyisocyanates are converted into nonionically hydrophilic modified polyisocyanates, which are particularly preferred for the use according to the present invention, by reaction with NCO-reactive compounds containing hydrophilicizing structural elements with nonionic groups or with polar groups which cannot be converted into ionic groups.
- the diisocyanate or polyisocyanate is present in stoichiometric excess in order that the resulting hydrophilic modified polyisocyanate may still contain free NCO groups.
- NCO-reactive compounds with hydrophilicizing structural elements are in particular hydroxyl-terminated polyethers of the general formula I
- R 8 is C 1 -C 20 -alkyl, in particular C 1 -C 4 -alkyl, or C 2 -C 20 -alkenyl, cyclopentyl, cyclohexyl, glycidyl, oxyethyl, phenyl, tolyl, benzyl, furfuryl or tetrahydrofurfuryl,
- E is sulfur or in particular oxygen
- D is propylene or especially ethylene, including in particular block-mixed ethoxylated and propoxylated compounds, and
- n is from 5 to 120, in particular 10 to 25.
- nonionically hydrophilic modified polyisocyanates which contain the polyethers I therefore also constitutes a preferred embodiment.
- C 1 -C 4 -alkanol-based ethylene oxide or propylene oxide polyethers having average molecular weights from 250 to 7 000, in particular from 450 to 1 500.
- nonionically hydrophilic modified polyisocyanates from diisocyanate or polyisocyanate and polyalkylene glycols of the formula HO-(DO) n -H, where D and n are each as defined above.
- the two terminal OH groups of the polyalkylene glycol both react with isocyanate.
- nonionically hydrophilic modified polyisocyanates are more particularly described in DE-A 24 47 135, DE-A 26 10 552, DE-A 29 08 844, EP-A 0 13 112, EP-A 019 844, DE-A 40 36 927, DE-A 41 36 618, EP-B 206 059, EP-A 464 781 and EP-A 516 361.
- the described diisocyanates and/or higher functionalized polyisocyanates are converted into anionically hydrophilic modified polyisocyanates by reaction with NCO-reactive compounds containing hydrophilicizing anionic groups, in particular acid groups such as carboxyl groups, sulfonic acid groups or phosphonic acid groups.
- NCO-reactive compounds containing hydrophilicizing anionic groups in particular acid groups such as carboxyl groups, sulfonic acid groups or phosphonic acid groups.
- the diisocyanate or polyisocyanate is present in stoichiometric excess in order that the resulting hydrophilic modified polyisocyanate may still contain free NCO groups.
- Suitable NCO-reactive compounds with anionic groups include in particular hydroxycarboxylic acids such as 2-hydroxyacetic acid, 3-hydroxypropionic acid, 4-hydroxybutyric acid or hydroxypivalic acid and 2,2,2-tris- and also 2,2-bis(hydroxymethyl)alkanoic acids, for example 2,2-bis(hydroxymethyl)acetic acid, 2,2-bis(hydroxymethyl)propionic acid, 2,2-bis(hydroxymethyl)butyric acid or 2,2,2-tris(hydroxymethyl)acetic acid.
- the carboxyl groups can be partly or wholly base-neutralized to be present in a water-soluble or water-dispersible form.
- the base used here is preferably a tertiary amine, which is known to be inert toward isocyanate.
- the described diisocyanates and/or higher functionalized polyisocyanates can also be reacted with a mixture of nonionically hydrophilic-modifying and anionically hydrophilic-modifying compounds, which are added in succession or simultaneously, for example with a deficiency of the polyethers I and the described hydroxycarboxylic acids.
- anionically hydrophilic modified polyisocyanates are more particularly described in DE-A 40 01 783, DE-A 41 13 160 and DE-A 41 42 275.
- the described diisocyanates and/or higher functionalized polyisocyanates are converted into cationically hydrophilic modified polyisocyanates by reaction with NCO-reactive compounds containing chemically built-in alkylatable or protonatable functions to form a cationic center. These functions are in particular tertiary nitrogen atoms, which are known to be inert toward isocyanate and to be readily quaternizable or protonatable. In the reaction of diisocyanate or polyisocyanate with these NCO-reactive compounds, the former are present in excess in order that the resulting hydrophilic modified polyisocyanate may still contain free NCO groups.
- Suitable such NCO-reactive compounds with tertiary nitrogen atoms are preferably aminoalcohols of the general formula II
- R 9 and R 10 are each linear or branched C 1 -C 20 -alkyl, in particular C 1 -C 5 -alkyl, or are together combined with the nitrogen atom into a five- or six-membered ring which may additionally contain an oxygen atom or a tertiary nitrogen atom, in particular a piperidine, morpholine, piperazine, pyrrolidine, oxazoline or dihydrooxazine ring, in which case the radicals R 9 and R 10 may additionally carry hydroxyl groups, in particular one hydroxyl group each, and
- R 11 is C 2 -C 10 -alkylene, in particular C 2 -C 6 -alkylene, which can be linear or branched.
- Suitable aminoalcohols II are in particular N-methyldiethanolamine, N-methyldi(iso)propanolamine, N-butyldiethanolamine, N-butyldi(iso)propanolamine, N-stearyldiethanolamine, N-stearyldi(iso)propanolamine, N,N-dimethylethanolamine, N,N-dimethyl(iso)propanolamine, N,N-diethylethanolamine, N,N-diethyl(iso)propanolamine, N,N-dibutylethanolamine, N,N-dibutyl(iso)propanolamine, triethanolamine, tri(iso)propanolamine, N-(2-hydroxyethyl)morpholine, N-(2-hydroxypropyl)morpholine, N-(2-hydroxyethyl)piperidine, N-(2-hydroxypropyl)piperidine, N-methyl-N′-
- Suitable such NCO-reactive compounds with tertiary nitrogen atoms further include preferably diamines of the general formula IIIa or IIIb
- R 9 to R 11 are each as defined above and R 12 is C 1 -C 5 -alkyl or is combined with R 9 into a five- or six-membered ring, in particular into a piperazine ring.
- Suitable diamines IIIa are in particular N,N-dimethyl-ethylenediamine, N,N-diethylethylenediamine, N,N-dimethyl-1,3-diamino-2,2-dimethylpropane, N,N-diethyl-1,3-propylenediamine, N-(3-aminopropyl)morpholine, N-(2-aminopropyl)morpholine, N-(3-aminopropyl)piperidine, N-(2-aminopropyl)piperidine, 4-amino--(N,N-diethylamino)pentane, 2-amino-1-(N,N-dimethylamino)propane, 2-amino-1-(N,N-diethylamino)propane or 2-amino-1-(,N-diethylamino)-2-methylpropane.
- Suitable diamines IIIb include in particular N,N,N′-trimethylethylenediamine, N,N,N′-triethylethylenediamine, N-methylpiperazine or N-ethylpiperazine.
- NCO-reactive compounds include polyether(poly)ols with built-in tertiary nitrogen atoms which are preparable by propoxylation and/or ethoxylation of initiator molecules containing amine nitrogen.
- polyether(poly)ols are for example the propoxylation and ethoxylation products of ammonia, ethanolamine, diethanolamine, ethylenediamine or N-methylaniline.
- NCO-reactive compounds are polyester and polyamide resins with tertiary nitrogen atoms, urethano-containing polyols with tertiary nitrogen atoms, and also polyhydroxypolyacrylates with tertiary nitrogen atoms.
- the described diisocyanates and/or higher functionalized polyisocyanates can also be reacted with a mixture of nonionically hydrophilic-modifying and cationically hydrophilic-modifying compounds, which are added in succession or simultaneously, for example with a deficiency of the polyethers I and the aminoalcohols II or the diamines IIIa or IIIb. It is also possible to use mixtures of nonionically hydrophilic-modifying and anionically hydrophilic-modifying compounds.
- hydrophilic modified polyisocyanates mentioned (A) can in general be used in aqueous media, adequate dispersibility of the polyisocyanates must be ensured.
- certain reaction products of di- or polyisocyanates and hydroxyl-terminated polyethers (polyether alcohols) such as the compounds I act as emulsifiers for this purpose.
- the good results which are obtained with the hydrophilic modified polyisocyanates (A) in aqueous media are all the more surprising since it had to be expected that isocyanates would rapidly decompose in aqueous medium.
- the polyisocyanates used according to this invention have a pot life of several hours in the aqueous liquor; that is, the instant polyisocyanate dispersions are stable during the customary processing time. A dispersion is said to be stable when its components remain dispersed in one another without their separating into discrete layers.
- pot life is meant the time during which the dispersions remain processible before they gel and set. Aqueous isocyanate dispersions gel and set because a reaction takes place between the water and the isocyanate to form a polyurea.
- the finish of the invention may comprise (B) one or more polyurethanes.
- polyurethanes are meant systems constructed from polyisocyanates (hereinafter also called monomers I) and polyisocyanate-reactive compounds having at least one hydroxyl group and optionally compounds having at least one primary or secondary amino group. Polyurethanes generally no longer contain any free isocyanate groups.
- Useful polyisocyanates for preparing the polyurethanes (B) in the finish include customary diisocyanates and/or customary more highly functional polyisocyanates as described under the hydrophilic modified polyisocyanates (A).
- customary diisocyanates and/or customary more highly functional polyisocyanates as described under the hydrophilic modified polyisocyanates (A).
- preference is given to aliphatic diisocyanates and aliphatic more highly functional polyisocyanates.
- the further constructional components of the polyurethane include initially polyols having a molecular weight of from 400 to 6 000 g/mol, preferably from 600 to 4 000 g/mol (monomers II).
- Polyetherpolyols or polyesterpolyols are contemplated in particular.
- Polyesterdiols are in particular the well-known reaction products of dihydric alcohols with dibasic carboxylic acids.
- free polycarboxylic acids it is also possible to use the corresponding polycarboxylic anhydrides or corresponding polycarboxylic esters of lower alcohols or mixtures thereof to prepare the polyesterpolyols.
- the polycarboxylic acids can be aliphatic, cycloaliphatic, aromatic or heterocyclic and can be unsaturated and/or substituted, for example by halogen atoms.
- Examples are succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, tetrachlorophthalic anhydride, endomethylenetetrahydrophthalic anhydride, glutaric anhydride, maleic acid, maleic anhydride, fumaric acid, dimeric fatty acids.
- Useful polyhydric alcohols include for example ethylene glycol, (1,2)-propylene glycol, (1,3)-propylene glycol, (1,4)-butanediol, (1,3)-butanediol, (1,4)-butenediol, (1,4)-butyndiol, (1,5)-pentanediol, (1,6)-hexanediol, (1,8)-octanediol, neopentylglycol, cyclohexanedimethanol, (1,4-bishydroxymethylcyclohexane), 2-methyl-1,3-propanediol, (1,5)-pentanediol, also diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycols.
- lactone-based polyesterdiols i.e., homo- or interpolymers of lactones, preferably terminally hydroxyl-functional addition products of lactones or lactone mixtures, for example ⁇ -caprolactone, ⁇ -propiolactone, ⁇ -butyrolactone and/or methyl- ⁇ -caprolactone, on suitable difunctional base molecules, for example the low molecular weight dihydric alcohols mentioned above as a constructional component for polyesterpolyols.
- the corresponding addition polymers of ⁇ -caprolactone are particularly preferred.
- lower polyesterdiols or polyetherdiols can be used as bases for preparing the lactone addition polymers.
- the addition polymers of lactones it is also possible to use the corresponding, chemically equivalent polycondensates of the hydroxycarboxylic acids corresponding to the lactones.
- Useful polyetherdiols are obtainable in particular by homopolymerization of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin, for example in the presence of BF 3 , or by addition of these compounds, optionally mixed or in succession, to base components having reactive hydrogen atoms, such as alcohols or amines, e.g., water, ethylene glycol, (1,3)-propylene glycol, (1,2)-propylene glycol, 4,4′-dihydroxydiphenylpropane and aniline.
- base components having reactive hydrogen atoms such as alcohols or amines, e.g., water, ethylene glycol, (1,3)-propylene glycol, (1,2)-propylene glycol, 4,4′-dihydroxydiphenylpropane and aniline.
- the fraction of the above-described monomers II is generally in the range from 0.1 to 0.8 gram equivalent, preferably from 0.2 to 0.7 gram equivalent, of the hydroxyl group of the monomer II based on 1 gram equivalent of isocyanate of the polyisocyanate.
- Further constructional components of the polyurethane include chain extenders or crosslinkers having at least two isocyanate-reactive groups selected from hydroxyl groups and primary or secondary amino groups.
- polyols especially diols and triols, having a molecular weight below 400 g/mol to 62 g/mol (monomers III).
- Useful polyols include in particular the above-recited diols and triols suitable for preparing polyesterpolyols and also more than trifunctional alcohols such as pentaerythritol or sorbitol.
- the fraction of monomer III is generally in the range from 0 to 0.8, especially from 0 to 0.7, gram equivalent, based on 1 gram equivalent of isocyanate.
- the optional monomers IV are at least difunctional amine chain extenders or crosslinkers of the molecular weight range from 32 to 500 g/mol, preferably from 60 to 300 g/mol, which contain at least two primary, two secondary or one primary and one secondary amino group.
- diamines such as diaminoethane, diaminopropanes, diaminobutanes, diaminohexanes, piperazine, 2,5-dimethylpiperazine, amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophoronediamine, IPDA), 4,4′-diaminodicyclohexylmethane, 1,4-diaminocyclohexanes, aminoethylethanolamine, hydrazine, hydrazine hydrate or triamines such as diethylenetriamine or 1,8-diamino-4-aminomethyloctane.
- diamines such as diaminoethane, diaminopropanes, diaminobutanes, diaminohexanes, piperazine, 2,5-dimethylpiperazine, amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophoronediamine, IPDA
- Amino-containing chain extenders may also be used in blocked form, for example in the form of the corresponding ketimines (see for example CA-1 129 128), ketazines (cf. for example U.S. Pat. No. 4,269,748) or amine salts (see U.S. Pat. No. 4,292,226).
- oxazolidines as used for example in U.S. Pat. No. 4,192,937, are capped polyamines which can be used to chain extend the prepolymers in the preparation of the polyurethanes of the present invention.
- capped polyamines When such capped polyamines are used, they are generally mixed with the prepolymers in the absence of water and this mixture is subsequently mixed with the dispersion water or a portion of the dispersion water, so that the corresponding polyamine intermediates are released hydrolytically.
- mixtures of di- and triamines particularly preferably mixtures of isophoronediamine and diethylenetriamine.
- the monomers V are aminoalcohols having a hydroxyl group and a primary or secondary amino group such as ethanolamine, isopropanolamine, methylethanolamine or aminoethoxyethanol.
- the fraction of monomer IV or V is in each case preferably in the range from 0 to 0.4, particularly preferably from 0 to 0.2, gram equivalent, based on 1 gram equivalent of isocyanate of the polyisocyanate.
- Useful constructional components further include compounds which have at least one, preferably two, isocyanate-reactive groups, i.e., hydroxyl or primary or secondary amino groups, and additionally, in contrast to the above-described monomers, ionic groups or potentially ionic groups which are convertible into ionic groups by a simple neutralizing or quaternizing reaction (monomers VI).
- monomers VI i.e., hydroxyl or primary or secondary amino groups
- the introduction of monomers VI renders the polyurethanes self-dispersible, i.e., no dispersing aids such as protective colloids or emulsifiers are needed for dispersion in water in this case.
- Cationic or anionic groups may be introduced by using compounds having (potential) cationic or (potential) anionic groups and isocyanate-reactive hydrogen atoms.
- These groups of compounds include for example polyethers having tertiary nitrogen atoms and preferably two terminal hydroxyl groups, as are obtainable for example in a conventional manner by alkoxylation of amines having two hydrogen atoms attached to the amine nitrogen, for example methylamine, aniline or N,N′-dimethylhydrazine.
- Polyethers of this kind generally have a molecular weight within the range from 500 to 6 000 g/mol.
- the ionic groups are introduced by using comparatively low molecular weight compounds having (potential) ionic groups and isocyanate-reactive groups. Examples thereof are recited in U.S. Pat. No. 3,479,310 and 4,056,564 and GB-1 455 554.
- dihydroxyphosphonates such as the sodium salt of ethyl 2,3-dihydroxypropanephosphonate, or the corresponding sodium salt of the unesterified phosphonic acid, can be used as ionic constructional component.
- Preferred (potential) ionic monomers VI are N-alkyldialkanolamines, for example N-methyldiethanolamine, N-ethyldiethanolamine, diaminosulfonates, such as the sodium salt of N-(2-aminoethyl)-2-aminoethanesulfonic acid, dihydroxysulfonates, dihydroxycarboxylic acids such as dimethylolpropionic acid, diaminocarboxylic acid or -carboxylates such as lysine or the sodium salt of N-(2-aminoethyl)-2-aminoethanecarboxylic acid and diamines having at least one additional tertiary amine nitrogen atom, e.g., N-methyl-bis-(3-aminopropyl)amine.
- N-alkyldialkanolamines for example N-methyldiethanolamine, N-ethyldiethanolamine, diaminosulfonates, such as the
- diamino- and dihydroxycarboxylic acids especially to the adduct of ethylenediamine with sodium acrylate or dimethylol-propionic acid.
- Potential ionic groups initially introduced into the polyaddition product are converted at least partly into ionic groups in a conventional manner by neutralization of the potential anionic or cationic groups or by quaternization of tertiary amine nitrogen atoms.
- Potential anionic groups for example carboxyl groups, are neutralized using inorganic and/or organic bases such as alkali metal hydroxides, carbonates or bicarbonates, ammonia or primary, secondary and particularly preferably tertiary amines such as triethylamine or dimethylaminopropanol.
- inorganic and/or organic bases such as alkali metal hydroxides, carbonates or bicarbonates, ammonia or primary, secondary and particularly preferably tertiary amines such as triethylamine or dimethylaminopropanol.
- useful neutralizing agents include inorganic or organic acids, for example hydrochloric acid, phosphoric acid, formic acid, acetic acid, fumaric acid, maleic acid, lactic acid, tartaric acid or oxalic acid, and useful quaternizing agents include for example methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, benzyl chloride, ethyl chloroacetate or bromoacetamide. Further neutralizing or quaternizing agents are described for example in U.S. Pat. No. 3,479,310 at column 6.
- This neutralization or quaternization of potential ionic groups can be effected before, during but preferably after the isocyanate polyaddition reaction.
- the amounts of monomer VI (the degree of neutralization or quaternization being taken into account in the case of components containing potential ionic groups) is suitably chosen so that the polyurethanes contain from 0.05 to 2, preferably 0.07 to 1.0, particularly preferably from 0.1 to 0.7, meq of ionic groups/g of polyurethane.
- monofunctional amine or hydroxyl compounds are also used as constructional components (monomers VII). They are preferably monohydric polyether alcohols of the molecular weight range from 500 to 10 000 g/mol, preferably from 800 to 5 000 g/mol. Monohydric polyether alcohols are obtainable for example by alkoxylation of monohydric base molecules, for example methanol, ethanol or n-butanol, using ethylene oxide or mixtures of ethylene oxide with other alkylene oxides, particularly propylene oxide, as alkoxylating agents. When alkylene oxide mixtures are used, however, they preferably contain not less than 40, particularly preferably not less than 65, mol % of ethylene oxide.
- the polyurethanes may thus optionally contain polyethylene oxide segments which are present in terminal polyether chains and which influence the hydrophilic character of the polyurethane as well as the ionic groups and ensure or improve dispersibility in water.
- the compounds of the type mentioned, if used, are preferably used in such amounts that from 0 to 10%, preferably 0 to 5%, by weight of polyethylene oxide units are introduced by them into the polyurethane.
- Useful monomers VIII which in contrast to the above monomers contain ethylenically unsaturated groups, include for example esters of acrylic or methacrylic acid with polyols in which at least one OH group of the polyol remains unesterified.
- the adducts of (meth)acrylic acid with bisglycidyl ethers of diols such as, for example, bisphenol A or butanediol.
- the fraction of ethylenically unsaturated groups is generally below 0.2 mol per 100 g of polyurethane.
- the total fraction of constructional components is preferably chosen in such a way that the sum total of isocyanate-reactive hydroxyl groups and primary or secondary amino groups is in the range from 0.9 to 1.2, particularly preferably from 0.95 to 1.1, based on 1 isocyanate group.
- polyurethane or, if a further reaction with amino-functional monomers IV or VI is intended, a polyurethane prepolymer still containing terminal isocyanate groups is preferably prepared in an inert water-miscible solvent, such as acetone, tetrahydrofuran, methyl ethyl ketone or N-methylpyrrolidone, from the monomers
- the reaction temperature is generally in the range from 20 to 160° C., preferably in the range from 50 to 100° C.
- the reaction of the diisocyanates can be speeded up using customary catalysts, such as dibutyltin dilaurate, tin(II) octoate or diazabicyclo-(2,2,2)-octane.
- customary catalysts such as dibutyltin dilaurate, tin(II) octoate or diazabicyclo-(2,2,2)-octane.
- the polyurethane prepolymer obtained can be further reacted with amino-functional compounds of monomers VI and optionally IV at 20 to 80° C., optionally after (further) dilution with solvents of the abovementioned kind, preferably with solvents having boiling points below 100° C.
- the organic solvent can be distilled off, if its boiling point is below that of water. Any higher-boiling solvents used can remain in the dispersion.
- the polyurethane content of the dispersions can be in particular in the range from 5 to 70% by weight, preferably in the range from 20 to 50% by weight, based on the dispersions.
- the dispersions may be additized with customary assistants, for example thickeners, thixotropicizers, oxidation and UV stabilizers or release agents.
- Hydrophobic assistants which may be difficult to disperse homogeneously in the finished dispersion, may also be added to the polyurethane or the prepolymer before dispersion, by the method described in U.S. Pat. No. 4,306,998.
- This invention also provides for the use of hydrophilic modified polyisocyanates (A) and polyurethanes (B) in finishes for wrinkleproofing cellulosic textiles.
- Finishes are any liquid formulations which contain the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form for application to the textile material.
- the finishes of the invention can be present for example as finishes in the narrower sense in the manufacture of textiles in the form of an aqueous washing liquor or as a liquid textile treatment.
- Useful solvents include for example water, alcohols such as methanol, ethanol and propanol, THF or mixtures thereof. It is possible for example to treat textiles with the finish in the course of their manufacture.
- Textiles which have not been adequately finished, if at all, may be treated with a textile treatment that contains the highly branched polymers for example before or after home laundering, for example during ironing. But it is also possible to treat the textiles with hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in the main wash cycle or after the main wash cycle in the refresher or rinse cycle of the washing machine.
- A hydrophilic modified polyisocyanate
- B polyurethane
- the present invention also provides for the use of the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in the manufacture of textiles, textile treatment before and after laundering, in the main wash cycle, the laundry rinse cycle and ironing. Different formulations are needed in each case.
- the treatment before or after laundering may utilize a textile treatment which, as well as hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form, contains a surfactant.
- the cellulosic textiles are for example sprayed with the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) with an add-on which is generally in the range from 0.01 to 10% by weight, preferably in the range from 0.1 to 7% by weight, particularly preferably in the range from 0.3 to 4% by weight, based on the weight of the dry textile material.
- the finish may also be applied to the textile material by dipping the textiles into a bath which contains generally from 0.1 to 10% by weight, preferably from 0.3 to 5% by weight, based on the weight of the dry textile material, of hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form.
- the textile material is either dipped only briefly into the bath or else allowed to dwell therein for a period of from 1 to 30 min for example.
- Cellulosic textiles which have been treated with the finish either by spraying or by dipping are if necessary squeezed off and dried. Drying may take place in air or else in a dryer or else by subjecting the treated textile material to hot ironing. The finish becomes fixed on the textile material in the course of drying. The best conditions in each case are readily ascertainable by experimentation.
- the temperatures for drying, including ironing are for example in the range from 40 to 150° C., preferably from 60 to 110° C.
- the cotton program of the iron is suitable in particular.
- Textiles treated with the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form according to the above-described process exhibit an excellent level of wrinkle and crease resistance that is durable to multiple laundering. There is frequently no longer any need to iron the textiles. The textiles thus treated additionally possess fiber and color protection.
- the invention also provides a textile treatment comprising
- components a) to e) adding up to 100% by weight are identical to components a) to e) adding up to 100% by weight.
- Preferred silicones are amino-containing silicones, which are preferably present in microemulsified form, alkoxylated, especially ethoxylated, silicones, polyalkylene oxide-polysiloxanes, polyalkylene oxide-aminopolydimethylsiloxanes, silicones having quaternary ammonium groups (silicone quats) and silicone surfactants.
- Useful softeners or lubricants include for example oxidized polyethylenes or paraffinic waxes and oils.
- Useful water-soluble, film-forming and adhesive polymers include for example (co)polymers based on acrylamide, N-vinylpyrrolidone, vinylformamide, N-vinylimidazole, vinylamine, N,N′-dialkylaminoalkyl (meth)acrylates, N,N′-dialkylaminoalkyl(meth)acrylamides, (meth)acrylic acid, alkyl (meth)acrylates and/or vinylsulfonate.
- the aforementioned basic monomers may also be used in quaternized form.
- a treatment formulation to be applied to the textile material by spraying may additionally include a spraying assistant.
- a spraying assistant in some cases, it can also be of advantage to include in the formulation alcohols such as ethanol, isopropanol, ethylene glycol or propylene glycol.
- Further customary additives are scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides and preservatives in customary amounts.
- the textile treatment may generally also be applied by spraying in the course of ironing after laundering. This not only substantially facilitates the ironing, but also imparts sustained wrinkle and crease resistance to the textiles.
- hydrophilic modified polyisocyanate (A) and/or the polyurethane (B) may also be used when the textiles are washed in the main wash cycle of the washing machine.
- the invention further provides a solid laundry detergent formulation comprising
- customary ingredients such as standardizers, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, dissolution improvers and/or disintegrants
- components a) to e) adding up to 100% by weight [0127] components a) to e) adding up to 100% by weight.
- Useful anionic surfactants are in particular:
- sulfated alkoxylated C 8 - to C 22 -alcohols (alkyl ether sulfates).
- Compounds of this kind are prepared for example by first alkoxylating a C 8 - to C 22 -alcohol, preferably a C 10 - to C 18 -alcohol, for example a fatty alcohol, and then sulfating the alkoxylation product.
- the alkoxylation is preferably carried out using ethylene oxide;
- linear C 8 to C 20 -alkylbenzenesulfonates LAS
- LAS preferably linear Cg- to C 1-3 -alkylbenzenesulfonates and -alkyltoluenesulfonates
- alkanesulfonates such as C 8 —to C 2-4 -alkanesulfonates, preferably C 10 - to C 18 -alkanesulfonates
- soaps such as, for example, the sodium and potassium salts of C 8 - to C 24 -carboxylic acids.
- the anionic surfactants mentioned are preferably included in the laundry detergent in the form of salts. Suitable cations in these salts are alkali metal ions such as sodium, potassium and lithium and ammonium ions such as hydroxyethyl ammonium, di(hydroxyethyl)ammonium and tri(hydroxyethyl)ammonium.
- Useful nonionic surfactants are in particular:
- alkoxylated C 8 - to C 22 -alcohols such as fatty alcohol alkoxylates or oxo alcohol alkoxylates. These may have been alkoxylated with ethylene oxide, propylene oxide and/or butylene oxide.
- Useful surfactants here include all alkoxylated alcohols which contain at least two molecules of one of the aforementioned alkylene oxides. Here it is possible to use block polymers of ethylene oxide, propylene oxide and/or butylene oxide or addition products which contain the aforementioned alkylene oxides in random distribution.
- Nonionic surfactants generally contain from 2 to 50, preferably from 3 to 20, mol of at least one alkylene oxide per mole of alcohol.
- the alkylene oxide component is preferably ethylene oxide.
- the alcohols preferably have from 10 to 18 carbon atoms. Depending on the type of alkoxylation catalyst used to make them, alkoxylates have a broad or narrow alkylene oxide homolog distribution;
- alkylphenol alkoxylates such as alkylphenol ethoxylates having C 6 - to C 14 -alkyl chains and from 5 to 30 alkylene oxide units;
- alkylpolyglucosides having from 8 to 22, preferably from 10 to 18, carbon atoms in the alkyl chain and generally from 1 to 20, preferably from 1.1 to 5, glucoside units;
- N-alkylglucamides fatty acid amide alkoxylates, fatty acid alkanolamide alkoxylates and also block copolymers of ethylene oxide, propylene oxide and/or butylene oxide.
- Useful inorganic builders are in particular:
- crystalline or amorphous aluminosilicates having ion-exchanging properties such as zeolites in particular.
- Useful zeolites include in particular zeolites A, X, B, P, MAP and HS in their sodium form or in forms in which sodium has been partly replaced by other cations such as lithium, potassium, calcium, magnesium or ammonium;
- crystalline silicates such as in particular disilicates or sheet-silicates, for example ⁇ -Na 2 Si 2 O 5 or ⁇ -Na 2 Si 2 O 5 .
- Silicates can be used in the form of their alkali metal, alkaline earth metal or ammonium salts, preferably as sodium, lithium and magnesium silicates;
- amorphous silicates such as for example sodium metasilicate or amorphous disilicate
- carbonates and bicarbonates are used in the form of their alkali metal, alkaline earth metal or ammonium salts. Preference is given to sodium, lithium and magnesium carbonates or bicarbonates, especially sodium carbonate and/or sodium bicarbonate;
- polyphosphates such as for example pentasodium triphosphate.
- Useful organic cobuilders include in particular low molecular weight, oligomeric or polymeric carboxylic acids.
- Useful low molecular weight carboxylic acids include for example citric acid, hydrophobic modified citric acid such as for example agaric acid, malic acid, tartaric acid, gluconic acid, glutaric acid, succinic acid, imidodisuccinic acid, oxydisuccinic acid, propanetricarboxylic acid, butanetetracarboxylic acid, cyclopentanetetracarboxylic acid, alkyl- and alkenylsuccinic acids and aminopolycarboxylic acids such as for example nitrilotriacetic acid, ⁇ -alaninediacetic acid, ethylenediaminetetraacetic acid, serinediacetic acid, isoserinediacetic acid, N-(2-hydroxyethyl)iminodiacetic acid, ethylenediaminedisuccinic acid and methyl- and ethylglycinediacetic acid;
- hydrophobic modified citric acid such as for example agaric acid,
- useful oligomeric or polymeric carboxylic acids include for example homopolymers of acrylic acid, oligomaleic acids, copolymers of maleic acid with acrylic acid, methacrylic acid, C 2 -C 22 -olefins such as for example isobutene or long-chain ⁇ -olefins, vinyl alkyl ethers having C 1 -C 8 -alkyl groups, vinyl acetate, vinyl propionate, (meth)acrylic esters of C 1 - to C 8 -alcohols and styrene. Preference is given to using the homopolymers of acrylic acid and copolymers of acrylic acid with maleic acid. Polyaspartic acids are also useful as organic cobuilders. Oligomeric and polymeric carboxylic acids are used in acid form or as sodium salt.
- a solid laundry detergent formulation according to the invention is customarily present in powder or granule form or in extrudate or tablet form.
- the invention further provides a liquid laundry detergent comprising
- customary ingredients such as sodium carbonate, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, nonaqueous solvents, solubilizers, hydrotropes, thickeners and/or alkanolamines,
- nonionic and anionic surfactants may be used.
- the concentration of the hydrophilic modified polyisocyanates or the polyurethanes in the wash liquor is for example in the range from 10 to 5 000 ppm, preferably in the range from 50 to 1 000 ppm.
- Textiles treated with the hydrophilic modified polyisocanates or polyurethanes in the main wash cycle of the washing machine not only wrinkle substantially less than untreated textiles, they are also easier to iron, softer and smoother, more dimensionally and shape stable and, because of their fiber and color protection, look less “used”, i.e., exhibit less fluff and fewer knots and less color damage or fading, after repeated washing.
- the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) may be used in the rinse or refresher cycle following the main wash cycle.
- concentration of the hydrophilic modified polyisocyanates or the polyurethanes in the wash liquor is for example in the range from 10 to 5 000 ppm, preferably in the range from 50 to 1000 ppm.
- the rinse liquor may if desired include ingredients typical for a fabric conditioner or refresher. Textiles treated in this way and then dried on the line or preferably in a tumble dryer likewise exhibit a very high level of crease resistance that is associated with the positive effects on ironing that were described above. Crease resistance can be substantially enhanced by briefly ironing the textiles once after drying.
- the treatment in the conditioning or refresher rinse cycle also has a favorable effect on the shape retention of the textiles. It further inhibits the formation of knots and fluff and suppresses color damage.
- the invention also provides a laundry refresher comprising
- components a) to e) adding up to 100% by weight [0167] components a) to e) adding up to 100% by weight.
- Preferred cationic surfactants are selected from the group of the quaternary diesterammonium salts, the quaternary tetraalkylammonium salts, the quaternary diamidoammonium salts, the amidoamine esters and imidazolium salts.
- Examples are quaternary diesterammonium salts which have two C 11 - to C 22 -alk(en)ylcarbonyloxy(mono- to pentamethylene) radicals and two C 1 - to C 3 -alkyl or -hydroxyalkyl radicals on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Quaternary diesterammonium salts further include in particular those which have a C 11 - to C 22 -alk(en)ylcarbonyloxytrimethylene radical bearing a C 11 - to C 22 -alk(en)ylcarbonyloxy radical on the central carbon atom of the trimethylene group and three C 1 - to C 3 -alkyl or -hydroxyalkyl radicals on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Quaternary tetraalkylammonium salts are in particular those which have two C 1 - to C 6 -alkyl radicals and two C 8 - to C 24 -alk(en)yl radicals on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Quaternary diamidoammonium salts are in particular those which bear two C 8 — to C 24 -alk(en)ylcarbonylaminoethylene radicals, a substituent selected from hydrogen, methyl, ethyl and polyoxyethylene having up to 5 oxyethylene units and as fourth radical a methyl group on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Amidoamino esters are in particular tertiary amines bearing a C 1 - to C 22 -alk(en)ylcarbonylamino(mono- to trimethylene) radical, a C 11 - to C 22 -alk(en)ylcarbonyloxy(mono- to trimethylene) radical and a methyl group as substituents on the nitrogen atom.
- Imidazolinium salts are in particular those which bear a C 14 - to C 18 -alk(en)yl radical in position 2 of the heterocycle, a C 14 - to C18-alk(en)ylcarbonyl(oxy or amino)ethylene radical on the neutral nitrogen atom and hydrogen, methyl or ethyl on the nitrogen atom carrying the positive charge, while counterions here are for example chloride, bromide, methosulfate or sulfate.
Abstract
A process for wrinkleproofing cellulosic textiles by treating the textiles with a finish and drying the treated textiles, whereby said finish comprises (A) one or more hydrophilic modified polyisocyanates and/or (B) one or more polyurethanes in dissolved or dispersed form.
Description
- This invention relates to processes for wrinkleproofing cellulosic textiles, wrinkleproofing finishes comprising hydrophilic modified polyisocyanates and/or polyurethanes, the use of the finishes and of the polyisocyanates and polyurethanes, and also textile treatments, solid and liquid laundry detergents and laundry refreshers comprising same.
- Cellulosic textiles are given easy care properties by treatment with condensation products of urea, glyoxal and formaldehyde, for example. The finish is applied during the manufacture of textile materials. Softening compounds are frequently further applied with the finish. Thus finished textiles are less wrinkled and creased, easier to iron and softer and smoother after laundering compared with untreated cellulose textiles.
- WO 92/01773 discloses the use of microemulsified aminosiloxanes in fabric conditioners to reduce wrinkling and creasing during the laundering process. In addition, the use of aminosiloxanes is said to facilitate ironing.
- WO 98/4772 discloses a process for pretreating textile materials by applying a mixture of a polycarboxylic acid and a cationic softener to the textile materials. Wrinkle control is obtained as a result.
- EP-A 0 300 525 discloses fabric conditioners based on crosslinkable amino-functionalized silicones that impart wrinkle control or an easy-iron effect to textiles treated therewith.
- WO 99/55953 discloses fabric wrinkle control compositions. They comprise lubricants, shape retention polymers, lithium salts and optionally further ingredients such as softeners, ionic and nonionic surfactants, odor control agents and bactericides. The formulation is preferably applied to the textile material by spraying.
- EP-A 0 978 556 describes a mixture of a softener and a crosslinker component having cationic properties as a fabric wrinkle and crease control composition and also a method of wrinkleproofing textiles.
- It is an object of the present invention to provide a further process for wrinkleproofing cellulosic textiles and also further finishes for wrinkleproofing such textiles.
- We have found that this object is achieved by a process for wrinkleproofing cellulosic textiles by treating the textiles with a finish and drying the treated textiles, which said finish comprises (A) one or more hydrophilic modified polyisocyanates and/or (B) one or more polyurethanes in dissolved or dispersed form.
- The invention also provides a wrinkleproofing finish for cellulosic textiles that comprises hydrophilic modified polyisocyanates and polyurethanes.
- Hydrophilic Modified Polyisocyanates
- The finish of the invention may include (A) one or more hydrophilic modified polyisocyanates.
- The hydrophilic modified polyisocyanates to be used according to this invention are based on customary diisocyanates and/or customary higher functional polyisocyanates having an average NCO functionality of from 2.0 to 4.5. These components can be present alone or mixed.
- Examples of customary diisocyanates are aliphatic diisocyanates such as tetramethylene diisocyanate, hexamethylene diisocyanate (1,6-diisocyanatohexane), octamethylene diisocyanate, decamethylene diisocyanate, dodecamethylene diisocyanate, tetradecamethylene diisocyanate, trimethylhexane diisocyanate or tetramethylhexane diisocyanate, cycloaliphatic diisocyanates such as 1,4-, 1,3- or 1,2-diisocyanatocyclohexane, 4,4′-di(isocyanatocyclohexyl)methane, 1-isocyanato-3,3,5-trimethyl-5-(isocyanatomethyl)cyclohexane (isophorone diisocyanate) or 2,4- or 2,6-diisocyanato-1-methylcyclohexane and also aromatic diisocyanates such as 2,4- or 2,6-tolylene diisocyanate, tetramethylxylylene diisocyanate, p-xylylene diisocyanate, 2,4′- or 4,4′-diisocyanatodiphenylmethane, 1,3- or 1,4-phenylene diisocyanate, 1-chloro-2,4-phenylene diisocyanate, 1,5-naphthylene diisocyanate, diphenylene 4,4′-diisocyanate, 4,4′-diisocyanato-3,3′-dimethyldiphenyl, 3-methyl-diphenylmethane 4,4′-diisocyanate or diphenyl ether 4,4′-diisocyanate. It is also possible for mixtures of the diisocyanates mentioned to be present. Preference is given among these to aliphatic diisocyanates, in particular to hexamethylene diisocyanate and isophorone diisocyanate.
- Suitable customary higher functional polyisocyanates are for example triisocyanates such as 2,4,6-triisocyanatotoluene or 2,4,4′-triisocyanatodiphenyl ether or the mixtures of di-, tri- and higher polyisocyanates which are obtained by phosgenation of corresponding aniline/formaldehyde condensates and are methylene-bridged polyphenyl polyisocyanates.
- Of particular interest are customary aliphatic higher functional polyisocyanates of the following groups:
- (a) isocyanurate-group-containing polyisocyanates of aliphatic and/or cycloaliphatic diisocyanates. Particular preference amongst these is given to the corresponding isocyanato-isocyanurates based on hexamethylene diisocyanate and isophorone diisocyanate. The present isocyanurates are in particular simple trisisocyanatoalkyl or triisocyanatocycloalkyl isocyanurates which are cyclic trimers of the diisocyanates, or mixtures with their higher homologs having more than one isocyanurate ring. The isocyanato-isocyanurates generally have an NCO content of from 10 to 30% by weight, in particular of from 15 to 25% by weight, and an average NCO functionality of from 2.6 to 4.5.
- (b) Uretidione-group-containing polyisocyanates having aliphatically and/or cycloaliphatically bound isocyanate groups, preferably derived from hexamethylene diisocyanate or isophorone diisocyanate. Uretidiones are cyclic dimerization products of two NCO groups.
- (c) Biuret-group-containing polyisocyanates having aliphatically bound isocyanate groups, in particular tris(6-isocyanatohexyl) biuret or its mixtures with its higher homologs. These biuret-group-containing polyisocyanates generally have an NCO content of from 18 to 25% by weight and an average NCO functionality of from 3 to 4.5.
- (d) Urethane- and/or allophanate-group-containing polyisocyanates with aliphatically or cycloaliphatically bound isocyanate groups, as obtainable for example by reacting excess amounts of hexamethylene diisocyanate or isophorone diisocyanate with simple polyhydric alcohols such as trimethylolpropane, glycerol, 1,2-dihydroxypropane or mixtures thereof. These urethano- and/or allophanato-containing polyisocyanates generally have an NCO content of from 12 to 20% by weight and an average NCO functionality of from 2.5 to 3.
- (e) Oxadiazinetrione-group-containing polyisocyanates, preferably derived from hexamethylene diisocyanate or isophorone diisocyanate. Such oxadiazinetriono-containing polyisocyanates are preparable from diisocyanate and carbon dioxide.
- (f) Uretoneimine-modified polyisocyanates.
- For the use according to the present invention, the described diisocyanates and/or higher functionalized polyisocyanates are converted into nonionically hydrophilic modified polyisocyanates, which are particularly preferred for the use according to the present invention, by reaction with NCO-reactive compounds containing hydrophilicizing structural elements with nonionic groups or with polar groups which cannot be converted into ionic groups. In this reaction, the diisocyanate or polyisocyanate, as the case may be, is present in stoichiometric excess in order that the resulting hydrophilic modified polyisocyanate may still contain free NCO groups.
- Suitable for use as such NCO-reactive compounds with hydrophilicizing structural elements are in particular hydroxyl-terminated polyethers of the general formula I
- R8-E-(DO)n-H (I)
- where
- R8 is C1-C20-alkyl, in particular C1-C4-alkyl, or C2-C20-alkenyl, cyclopentyl, cyclohexyl, glycidyl, oxyethyl, phenyl, tolyl, benzyl, furfuryl or tetrahydrofurfuryl,
- E is sulfur or in particular oxygen,
- D is propylene or especially ethylene, including in particular block-mixed ethoxylated and propoxylated compounds, and
- n is from 5 to 120, in particular 10 to 25.
- The use of nonionically hydrophilic modified polyisocyanates which contain the polyethers I therefore also constitutes a preferred embodiment.
- These are particularly preferably C1-C4-alkanol-based ethylene oxide or propylene oxide polyethers having average molecular weights from 250 to 7 000, in particular from 450 to 1 500.
- It is also possible to first react the described diisocyanates and/or higher functionalized polyisocyanates with a deficiency of hydroxyl-terminated polyesters, of other hydroxyl-terminated polyethers, or of polyols, for example ethylene glycol, trimethylolpropane or butanediol, to form prepolymers and then react these prepolymers subsequently or else simultaneously with the polyethers I in deficiency to form the hydrophilic modified polyisocyanates having free NCO groups.
- It is also possible to prepare nonionically hydrophilic modified polyisocyanates from diisocyanate or polyisocyanate and polyalkylene glycols of the formula HO-(DO)n-H, where D and n are each as defined above. In this reaction, the two terminal OH groups of the polyalkylene glycol both react with isocyanate.
- The recited types of nonionically hydrophilic modified polyisocyanates are more particularly described in DE-A 24 47 135, DE-A 26 10 552, DE-A 29 08 844, EP-A 0 13 112, EP-A 019 844, DE-A 40 36 927, DE-A 41 36 618, EP-B 206 059, EP-A 464 781 and EP-A 516 361.
- The described diisocyanates and/or higher functionalized polyisocyanates are converted into anionically hydrophilic modified polyisocyanates by reaction with NCO-reactive compounds containing hydrophilicizing anionic groups, in particular acid groups such as carboxyl groups, sulfonic acid groups or phosphonic acid groups. In this reaction, the diisocyanate or polyisocyanate is present in stoichiometric excess in order that the resulting hydrophilic modified polyisocyanate may still contain free NCO groups.
- Suitable NCO-reactive compounds with anionic groups include in particular hydroxycarboxylic acids such as 2-hydroxyacetic acid, 3-hydroxypropionic acid, 4-hydroxybutyric acid or hydroxypivalic acid and 2,2,2-tris- and also 2,2-bis(hydroxymethyl)alkanoic acids, for example 2,2-bis(hydroxymethyl)acetic acid, 2,2-bis(hydroxymethyl)propionic acid, 2,2-bis(hydroxymethyl)butyric acid or 2,2,2-tris(hydroxymethyl)acetic acid. The carboxyl groups can be partly or wholly base-neutralized to be present in a water-soluble or water-dispersible form. The base used here is preferably a tertiary amine, which is known to be inert toward isocyanate.
- The described diisocyanates and/or higher functionalized polyisocyanates can also be reacted with a mixture of nonionically hydrophilic-modifying and anionically hydrophilic-modifying compounds, which are added in succession or simultaneously, for example with a deficiency of the polyethers I and the described hydroxycarboxylic acids.
- The recited types of anionically hydrophilic modified polyisocyanates are more particularly described in DE-A 40 01 783, DE-A 41 13 160 and DE-A 41 42 275.
- The described diisocyanates and/or higher functionalized polyisocyanates are converted into cationically hydrophilic modified polyisocyanates by reaction with NCO-reactive compounds containing chemically built-in alkylatable or protonatable functions to form a cationic center. These functions are in particular tertiary nitrogen atoms, which are known to be inert toward isocyanate and to be readily quaternizable or protonatable. In the reaction of diisocyanate or polyisocyanate with these NCO-reactive compounds, the former are present in excess in order that the resulting hydrophilic modified polyisocyanate may still contain free NCO groups.
-
- where
- R9 and R10 are each linear or branched C1-C20-alkyl, in particular C1-C5-alkyl, or are together combined with the nitrogen atom into a five- or six-membered ring which may additionally contain an oxygen atom or a tertiary nitrogen atom, in particular a piperidine, morpholine, piperazine, pyrrolidine, oxazoline or dihydrooxazine ring, in which case the radicals R9 and R10 may additionally carry hydroxyl groups, in particular one hydroxyl group each, and
- R11 is C2-C10-alkylene, in particular C2-C6-alkylene, which can be linear or branched.
- Suitable aminoalcohols II are in particular N-methyldiethanolamine, N-methyldi(iso)propanolamine, N-butyldiethanolamine, N-butyldi(iso)propanolamine, N-stearyldiethanolamine, N-stearyldi(iso)propanolamine, N,N-dimethylethanolamine, N,N-dimethyl(iso)propanolamine, N,N-diethylethanolamine, N,N-diethyl(iso)propanolamine, N,N-dibutylethanolamine, N,N-dibutyl(iso)propanolamine, triethanolamine, tri(iso)propanolamine, N-(2-hydroxyethyl)morpholine, N-(2-hydroxypropyl)morpholine, N-(2-hydroxyethyl)piperidine, N-(2-hydroxypropyl)piperidine, N-methyl-N′-(2-hydroxyethyl)piperazine, N-methyl-N′-(2-hydroxypropyl)piperazine, N-methyl-N′-(4-hydroxybutyl)piperazine, 2-hydroxyethyloxazoline, 2-hydroxypropyloxazoline, 3-hydroxypropyloxazoline, 2-hydroxyethyldihydrooxazine, 2-hydroxypropyldihydrooxazine or 3-hydroxypropyldihydrooxazine.
-
- where R9 to R11 are each as defined above and R12 is C1-C5-alkyl or is combined with R9 into a five- or six-membered ring, in particular into a piperazine ring.
- Suitable diamines IIIa are in particular N,N-dimethyl-ethylenediamine, N,N-diethylethylenediamine, N,N-dimethyl-1,3-diamino-2,2-dimethylpropane, N,N-diethyl-1,3-propylenediamine, N-(3-aminopropyl)morpholine, N-(2-aminopropyl)morpholine, N-(3-aminopropyl)piperidine, N-(2-aminopropyl)piperidine, 4-amino--(N,N-diethylamino)pentane, 2-amino-1-(N,N-dimethylamino)propane, 2-amino-1-(N,N-diethylamino)propane or 2-amino-1-(,N-diethylamino)-2-methylpropane.
- Suitable diamines IIIb include in particular N,N,N′-trimethylethylenediamine, N,N,N′-triethylethylenediamine, N-methylpiperazine or N-ethylpiperazine.
- Further usable NCO-reactive compounds include polyether(poly)ols with built-in tertiary nitrogen atoms which are preparable by propoxylation and/or ethoxylation of initiator molecules containing amine nitrogen. Such polyether(poly)ols are for example the propoxylation and ethoxylation products of ammonia, ethanolamine, diethanolamine, ethylenediamine or N-methylaniline.
- Other usable NCO-reactive compounds are polyester and polyamide resins with tertiary nitrogen atoms, urethano-containing polyols with tertiary nitrogen atoms, and also polyhydroxypolyacrylates with tertiary nitrogen atoms.
- The described diisocyanates and/or higher functionalized polyisocyanates can also be reacted with a mixture of nonionically hydrophilic-modifying and cationically hydrophilic-modifying compounds, which are added in succession or simultaneously, for example with a deficiency of the polyethers I and the aminoalcohols II or the diamines IIIa or IIIb. It is also possible to use mixtures of nonionically hydrophilic-modifying and anionically hydrophilic-modifying compounds.
- The recited types of cationically hydrophilic modified polyisocyanates are more particularly described in DE-A 42 03 510 and EP-A 531 820.
- Since the hydrophilic modified polyisocyanates mentioned (A) can in general be used in aqueous media, adequate dispersibility of the polyisocyanates must be ensured. Preferably, within the group of the described hydrophilic modified polyisocyanates, certain reaction products of di- or polyisocyanates and hydroxyl-terminated polyethers (polyether alcohols) such as the compounds I act as emulsifiers for this purpose.
- The good results which are obtained with the hydrophilic modified polyisocyanates (A) in aqueous media are all the more surprising since it had to be expected that isocyanates would rapidly decompose in aqueous medium. Yet, the polyisocyanates used according to this invention have a pot life of several hours in the aqueous liquor; that is, the instant polyisocyanate dispersions are stable during the customary processing time. A dispersion is said to be stable when its components remain dispersed in one another without their separating into discrete layers. By “pot life” is meant the time during which the dispersions remain processible before they gel and set. Aqueous isocyanate dispersions gel and set because a reaction takes place between the water and the isocyanate to form a polyurea.
- Polyurethanes
- The finish of the invention may comprise (B) one or more polyurethanes.
- By polyurethanes are meant systems constructed from polyisocyanates (hereinafter also called monomers I) and polyisocyanate-reactive compounds having at least one hydroxyl group and optionally compounds having at least one primary or secondary amino group. Polyurethanes generally no longer contain any free isocyanate groups.
- Useful polyisocyanates for preparing the polyurethanes (B) in the finish include customary diisocyanates and/or customary more highly functional polyisocyanates as described under the hydrophilic modified polyisocyanates (A). Here too preference is given to aliphatic diisocyanates and aliphatic more highly functional polyisocyanates.
- The further constructional components of the polyurethane include initially polyols having a molecular weight of from 400 to 6 000 g/mol, preferably from 600 to 4 000 g/mol (monomers II).
- Polyetherpolyols or polyesterpolyols are contemplated in particular.
- Polyesterdiols are in particular the well-known reaction products of dihydric alcohols with dibasic carboxylic acids. Instead of the free polycarboxylic acids it is also possible to use the corresponding polycarboxylic anhydrides or corresponding polycarboxylic esters of lower alcohols or mixtures thereof to prepare the polyesterpolyols. The polycarboxylic acids can be aliphatic, cycloaliphatic, aromatic or heterocyclic and can be unsaturated and/or substituted, for example by halogen atoms. Examples are succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, tetrachlorophthalic anhydride, endomethylenetetrahydrophthalic anhydride, glutaric anhydride, maleic acid, maleic anhydride, fumaric acid, dimeric fatty acids. Useful polyhydric alcohols include for example ethylene glycol, (1,2)-propylene glycol, (1,3)-propylene glycol, (1,4)-butanediol, (1,3)-butanediol, (1,4)-butenediol, (1,4)-butyndiol, (1,5)-pentanediol, (1,6)-hexanediol, (1,8)-octanediol, neopentylglycol, cyclohexanedimethanol, (1,4-bishydroxymethylcyclohexane), 2-methyl-1,3-propanediol, (1,5)-pentanediol, also diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycols.
- It is also possible to use lactone-based polyesterdiols, i.e., homo- or interpolymers of lactones, preferably terminally hydroxyl-functional addition products of lactones or lactone mixtures, for example ε-caprolactone, β-propiolactone, γ-butyrolactone and/or methyl-ε-caprolactone, on suitable difunctional base molecules, for example the low molecular weight dihydric alcohols mentioned above as a constructional component for polyesterpolyols. The corresponding addition polymers of ε-caprolactone are particularly preferred. Similarly, lower polyesterdiols or polyetherdiols can be used as bases for preparing the lactone addition polymers. Instead of the addition polymers of lactones it is also possible to use the corresponding, chemically equivalent polycondensates of the hydroxycarboxylic acids corresponding to the lactones.
- Useful polyetherdiols, alone or mixed with polyesterdiols, are obtainable in particular by homopolymerization of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin, for example in the presence of BF3, or by addition of these compounds, optionally mixed or in succession, to base components having reactive hydrogen atoms, such as alcohols or amines, e.g., water, ethylene glycol, (1,3)-propylene glycol, (1,2)-propylene glycol, 4,4′-dihydroxydiphenylpropane and aniline.
- The fraction of the above-described monomers II is generally in the range from 0.1 to 0.8 gram equivalent, preferably from 0.2 to 0.7 gram equivalent, of the hydroxyl group of the monomer II based on 1 gram equivalent of isocyanate of the polyisocyanate.
- Further constructional components of the polyurethane include chain extenders or crosslinkers having at least two isocyanate-reactive groups selected from hydroxyl groups and primary or secondary amino groups.
- There may be mentioned polyols, especially diols and triols, having a molecular weight below 400 g/mol to 62 g/mol (monomers III).
- Useful polyols include in particular the above-recited diols and triols suitable for preparing polyesterpolyols and also more than trifunctional alcohols such as pentaerythritol or sorbitol.
- The fraction of monomer III is generally in the range from 0 to 0.8, especially from 0 to 0.7, gram equivalent, based on 1 gram equivalent of isocyanate.
- The optional monomers IV are at least difunctional amine chain extenders or crosslinkers of the molecular weight range from 32 to 500 g/mol, preferably from 60 to 300 g/mol, which contain at least two primary, two secondary or one primary and one secondary amino group.
- Examples thereof are diamines, such as diaminoethane, diaminopropanes, diaminobutanes, diaminohexanes, piperazine, 2,5-dimethylpiperazine, amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophoronediamine, IPDA), 4,4′-diaminodicyclohexylmethane, 1,4-diaminocyclohexanes, aminoethylethanolamine, hydrazine, hydrazine hydrate or triamines such as diethylenetriamine or 1,8-diamino-4-aminomethyloctane. Amino-containing chain extenders may also be used in blocked form, for example in the form of the corresponding ketimines (see for example CA-1 129 128), ketazines (cf. for example U.S. Pat. No. 4,269,748) or amine salts (see U.S. Pat. No. 4,292,226). Similarly, oxazolidines as used for example in U.S. Pat. No. 4,192,937, are capped polyamines which can be used to chain extend the prepolymers in the preparation of the polyurethanes of the present invention. When such capped polyamines are used, they are generally mixed with the prepolymers in the absence of water and this mixture is subsequently mixed with the dispersion water or a portion of the dispersion water, so that the corresponding polyamine intermediates are released hydrolytically.
- Preference is given to using mixtures of di- and triamines, particularly preferably mixtures of isophoronediamine and diethylenetriamine.
- The monomers V, optionally likewise used as chain extenders, are aminoalcohols having a hydroxyl group and a primary or secondary amino group such as ethanolamine, isopropanolamine, methylethanolamine or aminoethoxyethanol.
- The fraction of monomer IV or V is in each case preferably in the range from 0 to 0.4, particularly preferably from 0 to 0.2, gram equivalent, based on 1 gram equivalent of isocyanate of the polyisocyanate.
- Useful constructional components further include compounds which have at least one, preferably two, isocyanate-reactive groups, i.e., hydroxyl or primary or secondary amino groups, and additionally, in contrast to the above-described monomers, ionic groups or potentially ionic groups which are convertible into ionic groups by a simple neutralizing or quaternizing reaction (monomers VI). The introduction of monomers VI renders the polyurethanes self-dispersible, i.e., no dispersing aids such as protective colloids or emulsifiers are needed for dispersion in water in this case.
- Cationic or anionic groups may be introduced by using compounds having (potential) cationic or (potential) anionic groups and isocyanate-reactive hydrogen atoms. These groups of compounds include for example polyethers having tertiary nitrogen atoms and preferably two terminal hydroxyl groups, as are obtainable for example in a conventional manner by alkoxylation of amines having two hydrogen atoms attached to the amine nitrogen, for example methylamine, aniline or N,N′-dimethylhydrazine. Polyethers of this kind generally have a molecular weight within the range from 500 to 6 000 g/mol.
- Preferably, however, the ionic groups are introduced by using comparatively low molecular weight compounds having (potential) ionic groups and isocyanate-reactive groups. Examples thereof are recited in U.S. Pat. No. 3,479,310 and 4,056,564 and GB-1 455 554. Similarly, dihydroxyphosphonates, such as the sodium salt of ethyl 2,3-dihydroxypropanephosphonate, or the corresponding sodium salt of the unesterified phosphonic acid, can be used as ionic constructional component.
- Preferred (potential) ionic monomers VI are N-alkyldialkanolamines, for example N-methyldiethanolamine, N-ethyldiethanolamine, diaminosulfonates, such as the sodium salt of N-(2-aminoethyl)-2-aminoethanesulfonic acid, dihydroxysulfonates, dihydroxycarboxylic acids such as dimethylolpropionic acid, diaminocarboxylic acid or -carboxylates such as lysine or the sodium salt of N-(2-aminoethyl)-2-aminoethanecarboxylic acid and diamines having at least one additional tertiary amine nitrogen atom, e.g., N-methyl-bis-(3-aminopropyl)amine.
- Particular preference is given to diamino- and dihydroxycarboxylic acids, especially to the adduct of ethylenediamine with sodium acrylate or dimethylol-propionic acid.
- Potential ionic groups initially introduced into the polyaddition product, if desired, are converted at least partly into ionic groups in a conventional manner by neutralization of the potential anionic or cationic groups or by quaternization of tertiary amine nitrogen atoms.
- Potential anionic groups, for example carboxyl groups, are neutralized using inorganic and/or organic bases such as alkali metal hydroxides, carbonates or bicarbonates, ammonia or primary, secondary and particularly preferably tertiary amines such as triethylamine or dimethylaminopropanol.
- To convert potential cationic groups, for example tertiary amine groups into the corresponding cations, for example ammonium groups, useful neutralizing agents include inorganic or organic acids, for example hydrochloric acid, phosphoric acid, formic acid, acetic acid, fumaric acid, maleic acid, lactic acid, tartaric acid or oxalic acid, and useful quaternizing agents include for example methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, benzyl chloride, ethyl chloroacetate or bromoacetamide. Further neutralizing or quaternizing agents are described for example in U.S. Pat. No. 3,479,310 at column 6.
- This neutralization or quaternization of potential ionic groups can be effected before, during but preferably after the isocyanate polyaddition reaction.
- The amounts of monomer VI (the degree of neutralization or quaternization being taken into account in the case of components containing potential ionic groups) is suitably chosen so that the polyurethanes contain from 0.05 to 2, preferably 0.07 to 1.0, particularly preferably from 0.1 to 0.7, meq of ionic groups/g of polyurethane.
- Optionally, monofunctional amine or hydroxyl compounds are also used as constructional components (monomers VII). They are preferably monohydric polyether alcohols of the molecular weight range from 500 to 10 000 g/mol, preferably from 800 to 5 000 g/mol. Monohydric polyether alcohols are obtainable for example by alkoxylation of monohydric base molecules, for example methanol, ethanol or n-butanol, using ethylene oxide or mixtures of ethylene oxide with other alkylene oxides, particularly propylene oxide, as alkoxylating agents. When alkylene oxide mixtures are used, however, they preferably contain not less than 40, particularly preferably not less than 65, mol % of ethylene oxide.
- Owing to monomer VII, the polyurethanes may thus optionally contain polyethylene oxide segments which are present in terminal polyether chains and which influence the hydrophilic character of the polyurethane as well as the ionic groups and ensure or improve dispersibility in water.
- The compounds of the type mentioned, if used, are preferably used in such amounts that from 0 to 10%, preferably 0 to 5%, by weight of polyethylene oxide units are introduced by them into the polyurethane.
- Further examples of compounds useful as monomers I to VII in the preparation of the polyurethanes described are described for example in High Polymers, Vol. XVI, “Polyurethanes, Chemistry and Technology”, by Saunders-Frisch, Interscience Publishers, New York, London, Volume 1, 1962, pages 32 to 42 and pages 44 to 54 and Volume II, pages 5 to 6 and 198 to 199.
- Useful monomers VIII, which in contrast to the above monomers contain ethylenically unsaturated groups, include for example esters of acrylic or methacrylic acid with polyols in which at least one OH group of the polyol remains unesterified. Of particular suitability are hydroxyalkyl (meth)acrylates of the formula HO(CH2m)OOC(R12)C═CH2 (m=2 to 8; R12=H, CH3) and their positional isomers, mono(meth)acrylic esters of polyetherdiols as recited for example under monomer II, trimethylolpropane mono- and di(meth)acrylate, pentaerythritol di- and tri(meth)acrylate or reaction products of epoxy compounds with (meth)acrylic acid as mentioned for example in U.S. Pat. No. 357 221. Of particular suitability are the adducts of (meth)acrylic acid with bisglycidyl ethers of diols such as, for example, bisphenol A or butanediol.
- It is also possible to use adducts of (meth)acrylic acid with epoxidized diolefins, for example 3,4-epoxycyclohexylmethyl 3′,4′-epoxycyclohexanecarboxylate.
- Incorporation of monomer VIII makes the polyurethane, if desired, thermally or photochemically postcurable in the presence or absence of an initiator.
- The fraction of ethylenically unsaturated groups is generally below 0.2 mol per 100 g of polyurethane.
- The total fraction of constructional components is preferably chosen in such a way that the sum total of isocyanate-reactive hydroxyl groups and primary or secondary amino groups is in the range from 0.9 to 1.2, particularly preferably from 0.95 to 1.1, based on 1 isocyanate group.
- The preparation of the described polyurethanes, especially as dispersions, can be effected by customary methods as described for example in the above-cited references.
- The polyurethane or, if a further reaction with amino-functional monomers IV or VI is intended, a polyurethane prepolymer still containing terminal isocyanate groups is preferably prepared in an inert water-miscible solvent, such as acetone, tetrahydrofuran, methyl ethyl ketone or N-methylpyrrolidone, from the monomers
- I and II and optionally III, V, VI, VII and VIII, if VI contains no amino groups.
- The reaction temperature is generally in the range from 20 to 160° C., preferably in the range from 50 to 100° C.
- The reaction of the diisocyanates can be speeded up using customary catalysts, such as dibutyltin dilaurate, tin(II) octoate or diazabicyclo-(2,2,2)-octane.
- The polyurethane prepolymer obtained can be further reacted with amino-functional compounds of monomers VI and optionally IV at 20 to 80° C., optionally after (further) dilution with solvents of the abovementioned kind, preferably with solvents having boiling points below 100° C.
- The conversion of potential salt groups, for example carboxyl groups, or tertiary amino groups, which have been introduced into the polyurethane via monomer VI, into the corresponding ions is effected by neutralization with bases or acids or by quaternization of the tertiary amino groups before or during the dispersing of the polyurethane in water.
- After dispersion, the organic solvent can be distilled off, if its boiling point is below that of water. Any higher-boiling solvents used can remain in the dispersion.
- The polyurethane content of the dispersions can be in particular in the range from 5 to 70% by weight, preferably in the range from 20 to 50% by weight, based on the dispersions.
- The dispersions may be additized with customary assistants, for example thickeners, thixotropicizers, oxidation and UV stabilizers or release agents.
- Hydrophobic assistants, which may be difficult to disperse homogeneously in the finished dispersion, may also be added to the polyurethane or the prepolymer before dispersion, by the method described in U.S. Pat. No. 4,306,998.
- Use of hydrophilic modified polyisocyanates and polyurethanes
- This invention also provides for the use of hydrophilic modified polyisocyanates (A) and polyurethanes (B) in finishes for wrinkleproofing cellulosic textiles. Finishes are any liquid formulations which contain the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form for application to the textile material. The finishes of the invention can be present for example as finishes in the narrower sense in the manufacture of textiles in the form of an aqueous washing liquor or as a liquid textile treatment. Useful solvents include for example water, alcohols such as methanol, ethanol and propanol, THF or mixtures thereof. It is possible for example to treat textiles with the finish in the course of their manufacture. Textiles which have not been adequately finished, if at all, may be treated with a textile treatment that contains the highly branched polymers for example before or after home laundering, for example during ironing. But it is also possible to treat the textiles with hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in the main wash cycle or after the main wash cycle in the refresher or rinse cycle of the washing machine.
- The present invention also provides for the use of the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in the manufacture of textiles, textile treatment before and after laundering, in the main wash cycle, the laundry rinse cycle and ironing. Different formulations are needed in each case.
- Textile treatment, conditioner and refresher formulations
- The treatment before or after laundering may utilize a textile treatment which, as well as hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form, contains a surfactant. In this treatment, the cellulosic textiles are for example sprayed with the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) with an add-on which is generally in the range from 0.01 to 10% by weight, preferably in the range from 0.1 to 7% by weight, particularly preferably in the range from 0.3 to 4% by weight, based on the weight of the dry textile material. But the finish may also be applied to the textile material by dipping the textiles into a bath which contains generally from 0.1 to 10% by weight, preferably from 0.3 to 5% by weight, based on the weight of the dry textile material, of hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form. The textile material is either dipped only briefly into the bath or else allowed to dwell therein for a period of from 1 to 30 min for example.
- Cellulosic textiles which have been treated with the finish either by spraying or by dipping are if necessary squeezed off and dried. Drying may take place in air or else in a dryer or else by subjecting the treated textile material to hot ironing. The finish becomes fixed on the textile material in the course of drying. The best conditions in each case are readily ascertainable by experimentation. The temperatures for drying, including ironing, are for example in the range from 40 to 150° C., preferably from 60 to 110° C. For ironing, the cotton program of the iron is suitable in particular. Textiles treated with the hydrophilic modified polyisocyanate (A) and/or polyurethane (B) in dissolved or dispersed form according to the above-described process exhibit an excellent level of wrinkle and crease resistance that is durable to multiple laundering. There is frequently no longer any need to iron the textiles. The textiles thus treated additionally possess fiber and color protection.
- The invention also provides a textile treatment comprising
- a) from 0.1 to 40% by weight, preferably from 0.5 to 25% by weight, of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
- b) from 0 to 30% by weight of silicones,
- c) from 0 to 30% by weight of cationic and/or nonionic surfactants,
- d) from 0 to 60% by weight of further ingredients such as further wetting agents, softeners, lubricants, water-soluble, film-forming and adhesive polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides, preservatives and spraying assistants, and
- e) from 0 to 99.9% by weight of water,
- components a) to e) adding up to 100% by weight.
- Preferred silicones are amino-containing silicones, which are preferably present in microemulsified form, alkoxylated, especially ethoxylated, silicones, polyalkylene oxide-polysiloxanes, polyalkylene oxide-aminopolydimethylsiloxanes, silicones having quaternary ammonium groups (silicone quats) and silicone surfactants.
- Useful softeners or lubricants include for example oxidized polyethylenes or paraffinic waxes and oils. Useful water-soluble, film-forming and adhesive polymers include for example (co)polymers based on acrylamide, N-vinylpyrrolidone, vinylformamide, N-vinylimidazole, vinylamine, N,N′-dialkylaminoalkyl (meth)acrylates, N,N′-dialkylaminoalkyl(meth)acrylamides, (meth)acrylic acid, alkyl (meth)acrylates and/or vinylsulfonate. The aforementioned basic monomers may also be used in quaternized form.
- A treatment formulation to be applied to the textile material by spraying may additionally include a spraying assistant. In some cases, it can also be of advantage to include in the formulation alcohols such as ethanol, isopropanol, ethylene glycol or propylene glycol. Further customary additives are scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides and preservatives in customary amounts. The textile treatment may generally also be applied by spraying in the course of ironing after laundering. This not only substantially facilitates the ironing, but also imparts sustained wrinkle and crease resistance to the textiles.
- The hydrophilic modified polyisocyanate (A) and/or the polyurethane (B) may also be used when the textiles are washed in the main wash cycle of the washing machine.
- The invention further provides a solid laundry detergent formulation comprising
- a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
- b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
- c) from 0 to 50% by weight of an inorganic builder,
- d) from 0 to 10% by weight of an organic cobuilder,
- e) from 0 to 60% by weight of other customary ingredients such as standardizers, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, dissolution improvers and/or disintegrants,
- components a) to e) adding up to 100% by weight.
- Useful anionic surfactants are in particular:
- (fatty) alcohol sulfates of (fatty) alcohols having from 8 to 22, preferably from 10 to 18, carbon atoms, for example C9- to C11-alcohol sulfates, C12- to C1-4-alcohol sulfates, C12- to C1-8-alcohol sulfates, lauryl sulfate, cetyl sulfate, myristyl sulfate, palmityl sulfate, stearyl sulfate and tallow fatty alcohol sulfate;
- sulfated alkoxylated C8- to C22-alcohols (alkyl ether sulfates). Compounds of this kind are prepared for example by first alkoxylating a C8- to C22-alcohol, preferably a C10- to C18-alcohol, for example a fatty alcohol, and then sulfating the alkoxylation product. The alkoxylation is preferably carried out using ethylene oxide;
- linear C8 to C20-alkylbenzenesulfonates (LAS), preferably linear Cg- to C1-3-alkylbenzenesulfonates and -alkyltoluenesulfonates,
- alkanesulfonates such as C8—to C2-4-alkanesulfonates, preferably C10- to C18-alkanesulfonates
- soaps such as, for example, the sodium and potassium salts of C8- to C24-carboxylic acids.
- The anionic surfactants mentioned are preferably included in the laundry detergent in the form of salts. Suitable cations in these salts are alkali metal ions such as sodium, potassium and lithium and ammonium ions such as hydroxyethyl ammonium, di(hydroxyethyl)ammonium and tri(hydroxyethyl)ammonium.
- Useful nonionic surfactants are in particular:
- alkoxylated C8- to C22-alcohols such as fatty alcohol alkoxylates or oxo alcohol alkoxylates. These may have been alkoxylated with ethylene oxide, propylene oxide and/or butylene oxide. Useful surfactants here include all alkoxylated alcohols which contain at least two molecules of one of the aforementioned alkylene oxides. Here it is possible to use block polymers of ethylene oxide, propylene oxide and/or butylene oxide or addition products which contain the aforementioned alkylene oxides in random distribution. Nonionic surfactants generally contain from 2 to 50, preferably from 3 to 20, mol of at least one alkylene oxide per mole of alcohol. The alkylene oxide component is preferably ethylene oxide. The alcohols preferably have from 10 to 18 carbon atoms. Depending on the type of alkoxylation catalyst used to make them, alkoxylates have a broad or narrow alkylene oxide homolog distribution;
- alkylphenol alkoxylates such as alkylphenol ethoxylates having C6- to C14-alkyl chains and from 5 to 30 alkylene oxide units;
- alkylpolyglucosides having from 8 to 22, preferably from 10 to 18, carbon atoms in the alkyl chain and generally from 1 to 20, preferably from 1.1 to 5, glucoside units;
- N-alkylglucamides, fatty acid amide alkoxylates, fatty acid alkanolamide alkoxylates and also block copolymers of ethylene oxide, propylene oxide and/or butylene oxide.
- Useful inorganic builders are in particular:
- crystalline or amorphous aluminosilicates having ion-exchanging properties such as zeolites in particular. Useful zeolites include in particular zeolites A, X, B, P, MAP and HS in their sodium form or in forms in which sodium has been partly replaced by other cations such as lithium, potassium, calcium, magnesium or ammonium;
- crystalline silicates such as in particular disilicates or sheet-silicates, for example δ-Na2Si2O5 or β-Na2Si2O5. Silicates can be used in the form of their alkali metal, alkaline earth metal or ammonium salts, preferably as sodium, lithium and magnesium silicates;
- amorphous silicates such as for example sodium metasilicate or amorphous disilicate;
- carbonates and bicarbonates. These can be used in the form of their alkali metal, alkaline earth metal or ammonium salts. Preference is given to sodium, lithium and magnesium carbonates or bicarbonates, especially sodium carbonate and/or sodium bicarbonate;
- polyphosphates such as for example pentasodium triphosphate.
- Useful organic cobuilders include in particular low molecular weight, oligomeric or polymeric carboxylic acids.
- Useful low molecular weight carboxylic acids include for example citric acid, hydrophobic modified citric acid such as for example agaric acid, malic acid, tartaric acid, gluconic acid, glutaric acid, succinic acid, imidodisuccinic acid, oxydisuccinic acid, propanetricarboxylic acid, butanetetracarboxylic acid, cyclopentanetetracarboxylic acid, alkyl- and alkenylsuccinic acids and aminopolycarboxylic acids such as for example nitrilotriacetic acid, β-alaninediacetic acid, ethylenediaminetetraacetic acid, serinediacetic acid, isoserinediacetic acid, N-(2-hydroxyethyl)iminodiacetic acid, ethylenediaminedisuccinic acid and methyl- and ethylglycinediacetic acid;
- useful oligomeric or polymeric carboxylic acids include for example homopolymers of acrylic acid, oligomaleic acids, copolymers of maleic acid with acrylic acid, methacrylic acid, C2-C22-olefins such as for example isobutene or long-chain α-olefins, vinyl alkyl ethers having C1-C8-alkyl groups, vinyl acetate, vinyl propionate, (meth)acrylic esters of C1- to C8-alcohols and styrene. Preference is given to using the homopolymers of acrylic acid and copolymers of acrylic acid with maleic acid. Polyaspartic acids are also useful as organic cobuilders. Oligomeric and polymeric carboxylic acids are used in acid form or as sodium salt.
- A solid laundry detergent formulation according to the invention is customarily present in powder or granule form or in extrudate or tablet form.
- The invention further provides a liquid laundry detergent comprising
- a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
- b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
- c) from 0 to 20% by weight of an inorganic builder,
- d) from 0 to 10% by weight of an organic cobuilder,
- e) from 0 to 60% by weight of other customary ingredients such as sodium carbonate, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, nonaqueous solvents, solubilizers, hydrotropes, thickeners and/or alkanolamines,
- f) from 0 to 99.85% by weight of water, components a) to f) adding up to 100% by weight.
- The abovementioned nonionic and anionic surfactants, builders and cobuilders may be used.
- A detailed description of the laundry detergent ingredients mentioned is found for example in WO 99/06524 or WO 99/04313 and in Liquid Detergents, Editor: Kuo-Yann Lai, Surfactant Sci. Ser., Vol. 67, Marcel Decker, New York, 1997, pp. 272-304.
- The concentration of the hydrophilic modified polyisocyanates or the polyurethanes in the wash liquor is for example in the range from 10 to 5 000 ppm, preferably in the range from 50 to 1 000 ppm. Textiles treated with the hydrophilic modified polyisocanates or polyurethanes in the main wash cycle of the washing machine not only wrinkle substantially less than untreated textiles, they are also easier to iron, softer and smoother, more dimensionally and shape stable and, because of their fiber and color protection, look less “used”, i.e., exhibit less fluff and fewer knots and less color damage or fading, after repeated washing.
- The hydrophilic modified polyisocyanate (A) and/or polyurethane (B) may be used in the rinse or refresher cycle following the main wash cycle. The concentration of the hydrophilic modified polyisocyanates or the polyurethanes in the wash liquor is for example in the range from 10 to 5 000 ppm, preferably in the range from 50 to 1000 ppm. The rinse liquor may if desired include ingredients typical for a fabric conditioner or refresher. Textiles treated in this way and then dried on the line or preferably in a tumble dryer likewise exhibit a very high level of crease resistance that is associated with the positive effects on ironing that were described above. Crease resistance can be substantially enhanced by briefly ironing the textiles once after drying. The treatment in the conditioning or refresher rinse cycle also has a favorable effect on the shape retention of the textiles. It further inhibits the formation of knots and fluff and suppresses color damage.
- The invention also provides a laundry refresher comprising
- a) from 0.05 to 40% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
- b) from 0.1 to 40% by weight of a cationic surfactant,
- c) from 0 to 30% by weight of a nonionic surfactant,
- d) from 0 to 30% by weight of other customary ingredients such as silicones, other lubricants, wetting agents, film-forming polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides and preservatives, and
- e) from 0 to 99.85% by weight of water,
- components a) to e) adding up to 100% by weight.
- Preferred cationic surfactants are selected from the group of the quaternary diesterammonium salts, the quaternary tetraalkylammonium salts, the quaternary diamidoammonium salts, the amidoamine esters and imidazolium salts. Examples are quaternary diesterammonium salts which have two C11- to C22-alk(en)ylcarbonyloxy(mono- to pentamethylene) radicals and two C1- to C3-alkyl or -hydroxyalkyl radicals on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Quaternary diesterammonium salts further include in particular those which have a C11- to C22-alk(en)ylcarbonyloxytrimethylene radical bearing a C11- to C22-alk(en)ylcarbonyloxy radical on the central carbon atom of the trimethylene group and three C1- to C3-alkyl or -hydroxyalkyl radicals on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Quaternary tetraalkylammonium salts are in particular those which have two C1- to C6-alkyl radicals and two C8- to C24-alk(en)yl radicals on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Quaternary diamidoammonium salts are in particular those which bear two C8— to C24-alk(en)ylcarbonylaminoethylene radicals, a substituent selected from hydrogen, methyl, ethyl and polyoxyethylene having up to 5 oxyethylene units and as fourth radical a methyl group on the quaternary nitrogen atom and, for example, chloride, bromide, methosulfate or sulfate as counterion.
- Amidoamino esters are in particular tertiary amines bearing a C1- to C22-alk(en)ylcarbonylamino(mono- to trimethylene) radical, a C11- to C22-alk(en)ylcarbonyloxy(mono- to trimethylene) radical and a methyl group as substituents on the nitrogen atom.
- Imidazolinium salts are in particular those which bear a C14- to C18-alk(en)yl radical in position 2 of the heterocycle, a C14- to C18-alk(en)ylcarbonyl(oxy or amino)ethylene radical on the neutral nitrogen atom and hydrogen, methyl or ethyl on the nitrogen atom carrying the positive charge, while counterions here are for example chloride, bromide, methosulfate or sulfate.
Claims (21)
1. A process for wrinkleproofing cellulosic textiles by treating the textiles with a finish and drying the treated textiles, which said finish comprises (A) one or more hydrophilic modified polyisocyanates and/or (B) one or more polyurethanes in dissolved or dispersed form.
2. The use of hydrophilic modified polyisocyanates (A) and polyurethanes (B) in textile treatments, solid and liquid laundry detergents and laundry refreshers.
3. The use of finishes comprising at least one hydrophilic modified polyisocyanates (A) and/or at least one polyurethane (B) in textile manufacture, textile treatment, the laundry main wash cycle, the laundry rinse cycle and ironing.
4. A finish for wrinkleproofing cellulosic textiles, comprising at least one hydrophilic modified polyisocyanate (A) and at least one polyurethane (B).
5. A textile treatment comprising
a) from 0.1 to 40% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0 to 30% by weight of silicones,
c) from 0 to 30% by weight of cationic and/or nonionic surfactants,
d) from 0 to 60% by weight of further ingredients such as further wetting agents, softeners, lubricants, water-soluble, film-forming and adhesive polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides, preservatives and spraying assistants, and
e) from 0 to 99.9% by weight of water, the components adding up to 100% by weight.
6. A solid laundry detergent comprising
a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
c) from 0 to 50% by weight of an inorganic builder,
d) from 0 to 10% by weight of an organic cobuilder,
e) from 0 to 60% by weight of other customary ingredients such as standardizers, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, dissolution improvers and/or disintegrants,
components a) to e) adding up to 100% by weight.
7. A liquid laundry detergent comprising
a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane,
b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
c) from 0 to 20% by weight of an inorganic builder,
d) from 0 to 10% by weight of an organic cobuilder,
e) from 0 to 60% by weight of other customary ingredients such as sodium carbonate, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, nonaqueous solvents, solubilizers, hydrotropes, thickeners and/or alkanolamines,
f) from 0 to 99.85% by weight of water, components a) to f) adding up to 100% by weight.
8. A laundry refresher comprising
a) from 0.05 to 40% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 50% by weight of at least one cationic surfactant,
c) from 0 to 25% by weight of a nonionic surfactant,
d) from 0 to 30% by weight of other customary ingredients such as silicones, other lubricants, wetting agents, film-forming polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides and preservatives, and
e) from 0 to 99.85% by weight of water, components a) to e) adding up to 100% by weight.
6. (New) A method of use of hydrophilic modified polyisocyanates (A) or polyurethanes (B) as wrinkleproofing agent in home textile treatments, comprising the step of treating a textile with the textile treatments before or after home laundering.
7. (New) The method of use as claimed in claim 6 , wherein the textile treatment comprises
a) from 0.1 to 40% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0 to 30% by weight of silicones,
c) from 0 to 30% by weight of cationic and/or nonionic surfactants,
d) from 0 to 60% by weight of further ingredients such as further wetting agents, softeners, lubricants, water-soluble, film-forming and adhesive polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides, preservatives and spraying assistants, and
e) from 0 to 99.9% by weight of water, the components adding up to 100% by weight.
8. (New) The method of use as claimed in claim 6 , wherein the textile is treated during ironing.
9. (New) A method of use of hydrophilic modified polyisocyanates (A) and polyurethanes (B) as wrinkleproofing agent in a solid or liquid laundry detergents, comprising the step of washing a textile in the presence of the solid or liquid laundry detergent.
10. (New) The method of use as claimed in claim 9 , wherein the solid laundry detergent comprises
a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
c) from 0 to 50% by weight of an inorganic builder,
d) from 0 to 10% by weight of an organic cobuilder,
e) from 0 to 60% by weight of other customary ingredients such as standardizers, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, dissolution improvers and/or disintegrants,
components a) to e) adding up to 100% by weight.
11. (New) The method of use as claimed in claim 9 , wherein the liquid laundry detergent comprises
a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
c) from 0 to 20% by weight of an inorganic builder,
d) from 0 to 10% by weight of an organic cobuilder,
e) from 0 to 60% by weight of other customary ingredients such as sodium carbonate, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, nonaqueous solvents, solubilizers, hydrotropes, thickeners and/or alkanolamines,
f) from 0 to 99.85% by weight of water, components a) to f) adding up to 100% by weight.
12. (New) The method of use as claimed in claim 9 , wherein the solid or liquid laundry detergent is present in the main wash cycle of a washing machine.
13. (New) A method of use of hydrophilic modified polyisocyanates (A) or polyurethanes (B) as wrinkleproofing agent in laundry refreshers, comprising the step of rinsing a textile with a rinse liquor containing the laundry refresher.
14. (New) The method of use as claimed in claim 13 , wherein the laundry refresher comprises
a) from 0.05 to 40% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 50% by weight of at least one cationic surfactant,
c) from 0 to 25% by weight of a nonionic surfactant,
d) from 0 to 30% by weight of other customary ingredients such as silicones, other lubricants, wetting agents, film-forming polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides and preservatives, and
e) from 0 to 99.85% by weight of water, components a) to e) adding up to 100% by weight.
15. (new) The method of use as claimed in claim 13 , wherein the laundry refresher is present in the rinse or refresher cycle of a washing machine following the main wash cycle.
16. (New) A solid laundry detergent comprising
a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
c) from 0 to 50% by weight of an inorganic builder,
d) from 0 to 10% by weight of an organic cobuilder,
e) from 0 to 60% by weight of other customary ingredients such as standardizers, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inhibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, dissolution improvers and/or disintegrants, components a) to e) adding up to 100% by weight.
17. (New) A liquid laundry detergent comprising
a) from 0.05 to 20% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 40% by weight of at least one nonionic and/or anionic surfactant,
c) from 0 to 20% by weight of an inorganic builder,
d) from 0 to 10% by weight of an organic cobuilder,
e) from 0 to 60% by weight of other customary ingredients such as sodium carbonate, enzymes, perfume, complexing agents, corrosion inhibitors, bleaches, bleach activators, bleach catalysts, cationic surfactants, dye transfer inbibitors, antiredeposition agents, soil release polyesters, dyes, bactericides, nonaqueous solvents, solubilizers, hydrotropes, thickeners and/or alkanolamines,
f) from 0 to 99.85% by weight of water, components a) to f) adding up to 100% by weight.
18. (New) A laundry refresher comprising
a) from 0.05 to 40% by weight of at least one hydrophilic modified polyisocyanate (A) and/or at least one polyurethane (B),
b) from 0.1 to 50% by weight of at least one cationic surfactant,
c) from 0 to 25% by weight of a nonionic surfactant,
d) from 0 to 30% by weight of other customary ingredients such as silicones, other lubricants, wetting agents, film-forming polymers, scents, dyes, stabilizers, fiber and color protection additives, viscosity modifiers, soil release additives, corrosion control additives, bactericides and preservatives, and
e) from 0 to 99.85% by weight of water, components a) to e) adding up to 100% by weight.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10056163A DE10056163A1 (en) | 2000-11-13 | 2000-11-13 | Anticreasing finish, textile treatment, solid or liquid laundry detergent and laundry conditioner formulations for cellulose textiles, contain hydrophilic modified polyisocyanate and/or polyurethane |
DE10056163.2 | 2000-11-13 | ||
PCT/EP2001/013033 WO2002038852A1 (en) | 2000-11-13 | 2001-11-09 | Hydrophilically modified polyisocyanates and polyurethanes for crease-proofing textiles containing cellulose |
Publications (1)
Publication Number | Publication Date |
---|---|
US20040010858A1 true US20040010858A1 (en) | 2004-01-22 |
Family
ID=7663104
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/416,336 Abandoned US20040010858A1 (en) | 2000-11-13 | 2001-11-09 | Hydrophilically modified polyisocyanates and polyurethanes for crease-proofing textiles containing cellulose |
Country Status (12)
Country | Link |
---|---|
US (1) | US20040010858A1 (en) |
EP (1) | EP1379724B1 (en) |
JP (1) | JP2004513261A (en) |
CN (1) | CN1474891A (en) |
AT (1) | ATE298379T1 (en) |
AU (1) | AU2002217018A1 (en) |
BR (1) | BR0115302A (en) |
CA (1) | CA2426058A1 (en) |
DE (2) | DE10056163A1 (en) |
ES (1) | ES2241899T3 (en) |
MX (1) | MXPA03003147A (en) |
WO (1) | WO2002038852A1 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090029614A1 (en) * | 2004-10-08 | 2009-01-29 | Short Dan C | Ionized performance fabric |
US9242879B2 (en) | 2012-03-30 | 2016-01-26 | Ecolab Usa Inc. | Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water |
US9253978B2 (en) | 2008-03-28 | 2016-02-09 | Ecolab USA, Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9290448B2 (en) | 2008-03-28 | 2016-03-22 | Ecolab USA, Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9288992B2 (en) | 2013-03-05 | 2016-03-22 | Ecolab USA, Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US20160090560A1 (en) * | 2014-09-26 | 2016-03-31 | The Chemours Company Fc Llc | Method of imparting water repellency with non-fluorinated laundry treatment compositions |
US9540598B2 (en) | 2008-03-28 | 2017-01-10 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
US9585397B2 (en) | 2013-03-05 | 2017-03-07 | Ecolab Usa Inc. | Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring |
US9902627B2 (en) | 2011-12-20 | 2018-02-27 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
US10080481B2 (en) | 2005-02-10 | 2018-09-25 | G.I. View Ltd. | Advancement techniques for gastrointestinal tool with guiding element |
US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
CN109750498A (en) * | 2017-11-02 | 2019-05-14 | 丹阳八紫光能有限公司 | A kind of sofa cloth with aromatic odor |
JP2020504757A (en) * | 2016-12-30 | 2020-02-13 | オリパス コーポレーション | Exon skipping by peptide nucleic acid derivatives |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10226932A1 (en) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Radiation-curing coating agents |
DE10246836A1 (en) * | 2002-10-08 | 2004-04-22 | Saxol Chemie Gmbh | Anhydrous or water-containing composition for treating a hydrophilic paper product |
CN100402737C (en) * | 2005-07-18 | 2008-07-16 | 江苏阳光集团有限公司 | Ironing free shaped easy treating wool containing trousers and its production method |
MX2008012621A (en) * | 2006-04-04 | 2008-10-27 | Basf Se | Bleach systems enveloped with polymeric layers. |
CN104452149A (en) * | 2013-09-13 | 2015-03-25 | 上海鼎天纺织品有限公司 | Two-step finishing process of jacquard fabric fibers |
CN104389161B (en) * | 2014-11-04 | 2016-06-22 | 苏州经贸职业技术学院 | A kind of preparation method of crease-shedding real silk composite material |
CN105296187B (en) * | 2015-11-02 | 2018-01-19 | 浙江芬尼奇工贸有限公司 | A kind of liquid detergent based on branched fatty alcohol silicon-based polyurethane sulfonic acid type surfactant and preparation method thereof |
KR20200142772A (en) * | 2019-06-13 | 2020-12-23 | 폴프랜즈 주식회사 | A Method for Manufacturing Stretchable Socks for Infant and Socks Manufactured by the Same |
CN112391841B (en) * | 2020-11-16 | 2023-05-09 | 宁波丹盈服饰有限公司 | Manufacturing method of crease-resistant fabric |
CN112500939B (en) * | 2020-12-08 | 2022-01-04 | 福建植嘉生物科技有限公司 | Softening two-in-one laundry detergent and preparation method thereof |
CN113651936B (en) * | 2021-06-17 | 2023-03-31 | 厦门威亮光学涂层技术有限公司 | Application of organic sulfonic amine salt |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3905929A (en) * | 1973-03-23 | 1975-09-16 | Bayer Ag | Aqueous dispersions of polyurethane having side chain polyoxyethylene units |
US4068035A (en) * | 1975-04-23 | 1978-01-10 | Rhone-Poulenc Industries | Hydrophilic polyurethanes and textiles treated therewith |
US4433017A (en) * | 1981-09-17 | 1984-02-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Thermally reactive water-soluble blocked urethane prepolymer |
US4780101A (en) * | 1985-10-23 | 1988-10-25 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Resin treatment of cellulosic fiber-containing textile products |
US5306435A (en) * | 1991-07-11 | 1994-04-26 | Nihon Junyaku Co., Ltd. | Treating agent composition for leather, for fibrous materials |
US6057278A (en) * | 1996-05-03 | 2000-05-02 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic cotton soil release polymers |
US6251210B1 (en) * | 1996-08-07 | 2001-06-26 | Hi-Tex, Inc. | Treated textile fabric |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2334698A1 (en) * | 1975-12-09 | 1977-07-08 | Rhone Poulenc Ind | HYDROPHILIC POLYURETHANNES FOR USE IN DETERGENT COMPOSITIONS |
DE9107984U1 (en) * | 1991-06-28 | 1992-10-29 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen, De | |
DE4313262A1 (en) * | 1993-04-23 | 1994-10-27 | Pfersee Chem Fab | Process for the easy care of cellulose-containing fiber materials |
DE19744614A1 (en) * | 1997-10-09 | 1999-04-15 | Basf Ag | Aqueous impregnating liquid for easy-care textile finishing |
-
2000
- 2000-11-13 DE DE10056163A patent/DE10056163A1/en not_active Withdrawn
-
2001
- 2001-11-09 ES ES01993721T patent/ES2241899T3/en not_active Expired - Lifetime
- 2001-11-09 CA CA002426058A patent/CA2426058A1/en not_active Abandoned
- 2001-11-09 DE DE50106600T patent/DE50106600D1/en not_active Expired - Lifetime
- 2001-11-09 WO PCT/EP2001/013033 patent/WO2002038852A1/en active IP Right Grant
- 2001-11-09 EP EP01993721A patent/EP1379724B1/en not_active Expired - Lifetime
- 2001-11-09 CN CNA018187218A patent/CN1474891A/en active Pending
- 2001-11-09 MX MXPA03003147A patent/MXPA03003147A/en active IP Right Grant
- 2001-11-09 AT AT01993721T patent/ATE298379T1/en not_active IP Right Cessation
- 2001-11-09 JP JP2002541162A patent/JP2004513261A/en not_active Withdrawn
- 2001-11-09 AU AU2002217018A patent/AU2002217018A1/en not_active Abandoned
- 2001-11-09 US US10/416,336 patent/US20040010858A1/en not_active Abandoned
- 2001-11-09 BR BR0115302-1A patent/BR0115302A/en not_active Application Discontinuation
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3905929A (en) * | 1973-03-23 | 1975-09-16 | Bayer Ag | Aqueous dispersions of polyurethane having side chain polyoxyethylene units |
US4068035A (en) * | 1975-04-23 | 1978-01-10 | Rhone-Poulenc Industries | Hydrophilic polyurethanes and textiles treated therewith |
US4433017A (en) * | 1981-09-17 | 1984-02-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Thermally reactive water-soluble blocked urethane prepolymer |
US4780101A (en) * | 1985-10-23 | 1988-10-25 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Resin treatment of cellulosic fiber-containing textile products |
US5306435A (en) * | 1991-07-11 | 1994-04-26 | Nihon Junyaku Co., Ltd. | Treating agent composition for leather, for fibrous materials |
US6057278A (en) * | 1996-05-03 | 2000-05-02 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic cotton soil release polymers |
US6251210B1 (en) * | 1996-08-07 | 2001-06-26 | Hi-Tex, Inc. | Treated textile fabric |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7896928B2 (en) * | 2004-10-08 | 2011-03-01 | Stra, Llc | Ionized performance fabric composition |
US8292970B1 (en) | 2004-10-08 | 2012-10-23 | Stra, Llc | Ionized performance fabric |
US20090029614A1 (en) * | 2004-10-08 | 2009-01-29 | Short Dan C | Ionized performance fabric |
US10080481B2 (en) | 2005-02-10 | 2018-09-25 | G.I. View Ltd. | Advancement techniques for gastrointestinal tool with guiding element |
US10669512B2 (en) | 2008-03-28 | 2020-06-02 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US10077415B2 (en) | 2008-03-28 | 2018-09-18 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
US11827867B2 (en) | 2008-03-28 | 2023-11-28 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US11015151B2 (en) | 2008-03-28 | 2021-05-25 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9359295B2 (en) | 2008-03-28 | 2016-06-07 | Ecolab USA, Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9540598B2 (en) | 2008-03-28 | 2017-01-10 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
US10323218B2 (en) | 2008-03-28 | 2019-06-18 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9676711B2 (en) | 2008-03-28 | 2017-06-13 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9253978B2 (en) | 2008-03-28 | 2016-02-09 | Ecolab USA, Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9290448B2 (en) | 2008-03-28 | 2016-03-22 | Ecolab USA, Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US10017720B2 (en) | 2008-03-28 | 2018-07-10 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
US9902627B2 (en) | 2011-12-20 | 2018-02-27 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
US9242879B2 (en) | 2012-03-30 | 2016-01-26 | Ecolab Usa Inc. | Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water |
US10023484B2 (en) | 2012-03-30 | 2018-07-17 | Ecolab Usa Inc. | Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water |
US9926214B2 (en) | 2012-03-30 | 2018-03-27 | Ecolab Usa Inc. | Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water |
US10017403B2 (en) | 2012-03-30 | 2018-07-10 | Ecolab Usa Inc. | Use of peracetic acid/hydrogen peroxide and peroxide-reducing enzymes for treatment of drilling fluids, frac fluids, flowback water and disposal water |
US11180385B2 (en) | 2012-10-05 | 2021-11-23 | Ecolab USA, Inc. | Stable percarboxylic acid compositions and uses thereof |
US11026421B2 (en) | 2013-03-05 | 2021-06-08 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US9585397B2 (en) | 2013-03-05 | 2017-03-07 | Ecolab Usa Inc. | Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring |
US10893674B2 (en) | 2013-03-05 | 2021-01-19 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
US11206826B2 (en) | 2013-03-05 | 2021-12-28 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
US9288992B2 (en) | 2013-03-05 | 2016-03-22 | Ecolab USA, Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US10308898B2 (en) * | 2014-09-26 | 2019-06-04 | The Chemours Company Fc, Llc | Method of imparting water repellency with non-fluorinated laundry treatment compositions |
US20160090560A1 (en) * | 2014-09-26 | 2016-03-31 | The Chemours Company Fc Llc | Method of imparting water repellency with non-fluorinated laundry treatment compositions |
JP2020504757A (en) * | 2016-12-30 | 2020-02-13 | オリパス コーポレーション | Exon skipping by peptide nucleic acid derivatives |
JP7305542B2 (en) | 2016-12-30 | 2023-07-10 | オリパス コーポレーション | Exon skipping by peptide nucleic acid derivatives |
CN109750498A (en) * | 2017-11-02 | 2019-05-14 | 丹阳八紫光能有限公司 | A kind of sofa cloth with aromatic odor |
Also Published As
Publication number | Publication date |
---|---|
DE50106600D1 (en) | 2005-07-28 |
EP1379724A1 (en) | 2004-01-14 |
CN1474891A (en) | 2004-02-11 |
CA2426058A1 (en) | 2003-04-15 |
BR0115302A (en) | 2004-02-10 |
MXPA03003147A (en) | 2003-08-19 |
AU2002217018A1 (en) | 2002-05-21 |
WO2002038852A1 (en) | 2002-05-16 |
JP2004513261A (en) | 2004-04-30 |
ATE298379T1 (en) | 2005-07-15 |
EP1379724B1 (en) | 2005-06-22 |
DE10056163A1 (en) | 2002-05-23 |
ES2241899T3 (en) | 2005-11-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20040010858A1 (en) | Hydrophilically modified polyisocyanates and polyurethanes for crease-proofing textiles containing cellulose | |
US7141077B2 (en) | Hydrophobically modified polyethylenimines and polyvinylamines for wrinkle-resistant finishing of textiles containing cellulose | |
JP6272588B1 (en) | Water repellent agent and method for producing the same | |
US4068035A (en) | Hydrophilic polyurethanes and textiles treated therewith | |
US20040016060A1 (en) | Highly branched polymers for wrinkleproofing cellulosic textiles | |
US20050153865A1 (en) | Cationically modified, anionic polyurethane dispersions | |
JPS6124557A (en) | Fluorochemical allophanate | |
US10253450B2 (en) | Finishing agent with blocked polyisocyanates | |
US20040107506A1 (en) | Polysiloxane-containing polymers for wrinkleproofing cellulosic textiles | |
EP1106730B1 (en) | Treatment composition which provides anti-wrinkling properties to textiles | |
JP7206443B1 (en) | Method for manufacturing antibacterial and antiviral textile products | |
US5776394A (en) | Process for manufacturing cellulose fibres | |
KR20060128016A (en) | Fabric side-finishing method and products | |
CA2962601A1 (en) | Foam to deliver textile effect additives on fibrous articles | |
WO2023013691A1 (en) | Method for producing antibacterial/antiviral textile product | |
WO2008009606A1 (en) | Method for providing soft feel finish to textile fabrics |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: BASF AKTIENGESELLSCHAFT, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:DETERING, JUERGEN;NEUMANN, PETER;BRUCHMANN, BERND;REEL/FRAME:014667/0661 Effective date: 20030114 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |