US20020038482A1 - Use of liquid dyestuff preparations for dyeing wood - Google Patents
Use of liquid dyestuff preparations for dyeing wood Download PDFInfo
- Publication number
- US20020038482A1 US20020038482A1 US09/497,008 US49700800A US2002038482A1 US 20020038482 A1 US20020038482 A1 US 20020038482A1 US 49700800 A US49700800 A US 49700800A US 2002038482 A1 US2002038482 A1 US 2002038482A1
- Authority
- US
- United States
- Prior art keywords
- formula
- weight
- dyestuff
- glycol
- radicals
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 43
- 239000002023 wood Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 239000007788 liquid Substances 0.000 title claims abstract description 22
- 238000004043 dyeing Methods 0.000 title claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- -1 o-chlorophenylazo group Chemical group 0.000 claims description 11
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 5
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000000536 complexating effect Effects 0.000 claims description 4
- 238000007654 immersion Methods 0.000 claims description 4
- 241000208140 Acer Species 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 230000001680 brushing effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- 238000005096 rolling process Methods 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 claims description 2
- ODCMOZLVFHHLMY-UHFFFAOYSA-N 1-(2-hydroxyethoxy)hexan-2-ol Chemical compound CCCCC(O)COCCO ODCMOZLVFHHLMY-UHFFFAOYSA-N 0.000 claims description 2
- MLHQPPYBHZSBCX-UHFFFAOYSA-N 1-(2-hydroxyethoxy)propan-2-ol Chemical compound CC(O)COCCO MLHQPPYBHZSBCX-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- DEDUBNVYPMOFDR-UHFFFAOYSA-N 2-ethoxypropan-1-ol Chemical compound CCOC(C)CO DEDUBNVYPMOFDR-UHFFFAOYSA-N 0.000 claims description 2
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 claims description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 2
- VKCROHJIGLNYSC-UHFFFAOYSA-N 3-(3-ethoxypropoxy)propan-1-ol Chemical compound CCOCCCOCCCO VKCROHJIGLNYSC-UHFFFAOYSA-N 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- 240000005020 Acaciella glauca Species 0.000 claims description 2
- 235000018185 Betula X alpestris Nutrition 0.000 claims description 2
- 235000018212 Betula X uliginosa Nutrition 0.000 claims description 2
- 235000014036 Castanea Nutrition 0.000 claims description 2
- 241001070941 Castanea Species 0.000 claims description 2
- 240000009226 Corylus americana Species 0.000 claims description 2
- 235000001543 Corylus americana Nutrition 0.000 claims description 2
- 235000007466 Corylus avellana Nutrition 0.000 claims description 2
- 240000000731 Fagus sylvatica Species 0.000 claims description 2
- 235000010099 Fagus sylvatica Nutrition 0.000 claims description 2
- 240000007049 Juglans regia Species 0.000 claims description 2
- 235000009496 Juglans regia Nutrition 0.000 claims description 2
- 241000218652 Larix Species 0.000 claims description 2
- 235000005590 Larix decidua Nutrition 0.000 claims description 2
- 241000218657 Picea Species 0.000 claims description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 2
- 241000018646 Pinus brutia Species 0.000 claims description 2
- 235000011613 Pinus brutia Nutrition 0.000 claims description 2
- 235000008582 Pinus sylvestris Nutrition 0.000 claims description 2
- 241000219000 Populus Species 0.000 claims description 2
- 235000014443 Pyrus communis Nutrition 0.000 claims description 2
- 240000001987 Pyrus communis Species 0.000 claims description 2
- 241000219492 Quercus Species 0.000 claims description 2
- 235000016976 Quercus macrolepis Nutrition 0.000 claims description 2
- 241000124033 Salix Species 0.000 claims description 2
- 244000186561 Swietenia macrophylla Species 0.000 claims description 2
- 240000002871 Tectona grandis Species 0.000 claims description 2
- 240000007313 Tilia cordata Species 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 2
- 235000020234 walnut Nutrition 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 0 C.O=S(=O)(O)*1CO[Cr]2(O[2H]*=NCCO2)OBN=N1 Chemical compound C.O=S(=O)(O)*1CO[Cr]2(O[2H]*=NCCO2)OBN=N1 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZULLGCPFJARRLH-UHFFFAOYSA-N C.CC1=CC(Cl)=CC=C1O.CC1=CC(S(N)(=O)=O)=CC=C1O.CC1=CC([N+](=O)[O-])=CC=C1O.CC1=CC=CC=C1C(=O)O Chemical compound C.CC1=CC(Cl)=CC=C1O.CC1=CC(S(N)(=O)=O)=CC=C1O.CC1=CC([N+](=O)[O-])=CC=C1O.CC1=CC=CC=C1C(=O)O ZULLGCPFJARRLH-UHFFFAOYSA-N 0.000 description 2
- IHWHLCMOAGWOIQ-UHFFFAOYSA-N CC1=C(O)C=CC2=CC=CC=C21.CC1=CC=C(N2N=C(C)C(C)=C2O)C=C1.CC1=NN(C2=CC=CC=C2)C(O)=C1C Chemical compound CC1=C(O)C=CC2=CC=CC=C21.CC1=CC=C(N2N=C(C)C(C)=C2O)C=C1.CC1=NN(C2=CC=CC=C2)C(O)=C1C IHWHLCMOAGWOIQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- GWCFTYITFDWLAY-UHFFFAOYSA-N 1-ethylazepan-2-one Chemical compound CCN1CCCCCC1=O GWCFTYITFDWLAY-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
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- MDXTXVUTYJJPPT-UHFFFAOYSA-N C.CC1=CC(C(=O)O)=C(C)C=C1.CC1=CC(C)=C(O)C(C)=C1.CC1=CC(C)=C(O)C(C)=C1.CC1=CC(Cl)=CC(C)=C1O.CC1=CC(O)=C(C)C2=CC=CC=C12.CC1=CC=C2C(=C1)C(C)=CC(O)=C2C Chemical compound C.CC1=CC(C(=O)O)=C(C)C=C1.CC1=CC(C)=C(O)C(C)=C1.CC1=CC(C)=C(O)C(C)=C1.CC1=CC(Cl)=CC(C)=C1O.CC1=CC(O)=C(C)C2=CC=CC=C12.CC1=CC=C2C(=C1)C(C)=CC(O)=C2C MDXTXVUTYJJPPT-UHFFFAOYSA-N 0.000 description 1
- AXPGJVQDFGMUFI-UHFFFAOYSA-J CC1=CC2=C(C=C1)N=NC1=C(O[Cr]3(OC(=O)C4=CC=CC=C4N=CC4=CC(N=NC5=CC(Cl)=CC=C5Cl)=CC=C4O3)OC2=O)N(C2=CC=CC=C2)N=C1C Chemical compound CC1=CC2=C(C=C1)N=NC1=C(O[Cr]3(OC(=O)C4=CC=CC=C4N=CC4=CC(N=NC5=CC(Cl)=CC=C5Cl)=CC=C4O3)OC2=O)N(C2=CC=CC=C2)N=C1C AXPGJVQDFGMUFI-UHFFFAOYSA-J 0.000 description 1
- NDTYIIPBUCWMQN-UHFFFAOYSA-J CC1=CC2=C(C=C1)N=NC1=C(O[Cr]3(OC2=O)OC2=CC=C(N=NC4=CC=C([N+](=O)[O-])C=C4Cl)C=C2C=NC2=C(C=CC(S(N)(=O)=O)=C2)O3)N(C2=CC=CC=C2)N=C1C Chemical compound CC1=CC2=C(C=C1)N=NC1=C(O[Cr]3(OC2=O)OC2=CC=C(N=NC4=CC=C([N+](=O)[O-])C=C4Cl)C=C2C=NC2=C(C=CC(S(N)(=O)=O)=C2)O3)N(C2=CC=CC=C2)N=C1C NDTYIIPBUCWMQN-UHFFFAOYSA-J 0.000 description 1
- PFCAEDHDPKZWCR-UHFFFAOYSA-J CC1=CC2=C(N=NC3=C(C=CC4=CC=CC=C43)O[Cr]3(OC4=CC=C([N+](=O)[O-])C=C4N=NC4=C5C=CC=CC5=CC=C4O3)O2)C2=CC=C([N+](=O)[O-])C=C12 Chemical compound CC1=CC2=C(N=NC3=C(C=CC4=CC=CC=C43)O[Cr]3(OC4=CC=C([N+](=O)[O-])C=C4N=NC4=C5C=CC=CC5=CC=C4O3)O2)C2=CC=C([N+](=O)[O-])C=C12 PFCAEDHDPKZWCR-UHFFFAOYSA-J 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- RKMMLQUVSRGFBF-UHFFFAOYSA-J O=S(=O)(O)C1=CC2=C(N=NC3=C(C=CC4=CC=CC=C43)O[Cr]3(OC4=CC=C(Cl)C=C4N=NC4=C5C=CC=CC5=CC=C4O3)O2)C2=CC=CC=C21 Chemical compound O=S(=O)(O)C1=CC2=C(N=NC3=C(C=CC4=CC=CC=C43)O[Cr]3(OC4=CC=C(Cl)C=C4N=NC4=C5C=CC=CC5=CC=C4O3)O2)C2=CC=CC=C21 RKMMLQUVSRGFBF-UHFFFAOYSA-J 0.000 description 1
- VTODJLNXKBBAFU-UHFFFAOYSA-F O=[N+]([O-])C1=CC=C(N=NC2=CC=C3O[Cr]4(OC5=CC=C([N+](=O)[O-])C=C5N=CC3=C2)OC2=C(N=NC3=C(O4)C(S(=O)(=O)O)=CC(Cl)=C3)C3=CC=CC=C3C=C2)C(Cl)=C1.O=[N+]([O-])C1=CC=C(N=NC2=CC=C3O[Cr]4(OC5=CC=C([N+](=O)[O-])C=C5N=CC3=C2)OC2=C(N=NC3=C(O4)C(S(=O)(=O)O)=CC([N+](=O)[O-])=C3)C3=CC=CC=C3C=C2)C(Cl)=C1 Chemical compound O=[N+]([O-])C1=CC=C(N=NC2=CC=C3O[Cr]4(OC5=CC=C([N+](=O)[O-])C=C5N=CC3=C2)OC2=C(N=NC3=C(O4)C(S(=O)(=O)O)=CC(Cl)=C3)C3=CC=CC=C3C=C2)C(Cl)=C1.O=[N+]([O-])C1=CC=C(N=NC2=CC=C3O[Cr]4(OC5=CC=C([N+](=O)[O-])C=C5N=CC3=C2)OC2=C(N=NC3=C(O4)C(S(=O)(=O)O)=CC([N+](=O)[O-])=C3)C3=CC=CC=C3C=C2)C(Cl)=C1 VTODJLNXKBBAFU-UHFFFAOYSA-F 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- MBJUMIJKDKJBBG-UHFFFAOYSA-J [H]N1N=C(C)C2=C1O[Cr]1(OC3=CC=C(Cl)C=C3N=N2)OC2=C(C=C(S(=O)(=O)O)C=C2[N+](=O)[O-])N=NC2=C(O1)N(C1=CC=C(C)C=C1)N=C2C Chemical compound [H]N1N=C(C)C2=C1O[Cr]1(OC3=CC=C(Cl)C=C3N=N2)OC2=C(C=C(S(=O)(=O)O)C=C2[N+](=O)[O-])N=NC2=C(O1)N(C1=CC=C(C)C=C1)N=C2C MBJUMIJKDKJBBG-UHFFFAOYSA-J 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940006487 lithium cation Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
Definitions
- the invention relates to the use of liquid dyestuff preparations for dyeing wood.
- Liquid dyestuff preparations for dyeing wood are usually called woodstains. Woodstains are intended not to mask but to emphasize the grain of the wood and its veneers, giving them colour, and therefore comprise only truly dissolved dyestuffs. Solutions of basic or acidic dyestuffs in water or of solvent dyestuffs in organic solvents are known in practice. In addition to these so-called water-based and solvent-based stains, a combination of these two stains became established at the start of the '80s as a further type. These are water-dilutable solutions of organic dyestuffs in mixtures of water and solvent.
- Woodstains are chiefly employed indoors and serve chiefly for decorative purposes. On application with a sponge, brush or a spray gun, they should penetrate as uniformly as possible and as deeply as possible into the wood material and give a uniform dyeing which is fast to light, water and abrasion after drying. It should furthermore also be possible to protect and preserve the stained wood with clear furniture varnishes without the dyestuffs bleeding out into the clear varnish.
- Woodstains chiefly comprise metal complex dyestuffs.
- the invention relates to the use of liquid dyestuff preparations for dyeing wood, characterized in that the liquid dyestuff preparations comprising
- n 1 and n 2 denote the number 1 or 0,
- X represents N or CH
- Ct + represents a cation
- the polyvalent radicals A, B, G and D independently of one another represent heterocyclic or aromatic radicals, in particular optionally substituted phenylene and naphthylene radicals, the particular complexing —COO— or —O— group being in the ortho-position relative to the azo and azomethine group (X ⁇ CH) respectively,
- R denotes a straight-chain or branched C 1 -C 4 -alkyl
- Z denotes a straight-chain or branched C 2 -C 3 -alkylene
- n 3 represents 1, 2 or 3
- liquid is understood as meaning a liquid state at room temperature under normal pressure.
- dyestuff preparations which comprise dyestuffs of the formula (I) which are preferably built up from azo or azomethine compounds which, in the form of their free acid, correspond to the compounds (III) and (IV)
- Preferred dyestuffs of the formula (I) are derived from the following radicals:
- Possible radicals of the formula —B—OH are, preferably:
- Possible radicals of the formula -G-(CO)n 2 OH are, preferably:
- Possible radicals of the formula -D-OH are, preferably:
- Dyestuffs which are employed as further preferred dyestuffs of the formula (I) are those of the formula (V):
- A, B, G, D, n 1 , n 2 and Ct + have the abovementioned meanings, and
- m 0 or 1
- Preferred substituents of the polyvalent radicals A, B, G and D are, for example, those chosen from the group consisting of: NO 2 , halogen, in particular chlorine, sulphonamide and C 1 -C 4 -alkyl.
- the dyestuffs of the formula (I) which can be used according to the invention are known in most cases and can be prepared by known methods, such as are described, for example, in EP-A 066 230, EP-A 072 501 or EP-A 532 994.
- the cation represented by Ca + is preferably an alkali metal cation, in particular a lithium, sodium or potassium cation, an ammonium ion, the cation of an organic amine, such as, for example, that of mono-, di- or triethylamine, mono-, di- or tri-ethanolamine, N-methyldiethanolamine, N-butyldiethanolamine or N,N-diethylethanolamine, or a tetraalkylammonium, such as, for example, tetramethylammonium.
- a particularly preferred cation is the lithium cation.
- Preferred dyestuffs of the formula I correspond to a dyestuff of the formula (Ia) (yellow)
- Preferred alkoxy-alcohols of the formula (II) which are mentioned are, for example, the following representatives: C 1 -C 4 -monoalkyl ethers of mono- and polyglycols, such as methyl glycol, ethyl glycol, propyl glycol, butyl glycol, methyldiethylene glycol, butyldiethylene glycol, methyltriethylene glycol, 1-methoxy-2-propanol, 2-methoxy-1-propanol, 1-ethoxy-2-propanol, 2-ethoxy-1-propanol, dipropylene glycol monomethyl ether means (3-(3-methoxy-propoxy)-1-propanol) and dipropylene glycol monoethyl ether means (3-(3-ethoxy-1-propoxy)-1-propanol).
- alkoxy-alcohols of the formula (II) are the C 1 -C 4 -monoalkyl ethers of glycols and diglycols and the monoalkyl ethers of 1,2-propylene glycol and of ethylene glycol, in particular monoalkyl ethers of 1,2-propylene glycol.
- 1-Ethoxy-2-propanol is especially preferred.
- the dyestuff preparations used according to the invention can furthermore comprise
- auxiliaries customary in woodstains such as fungicides, UV stabilizers, binders and/or surfactants.
- Possible preferred cyclic esters or amides are, for example, lactones, such as 4-butyrolactone, and lactams, such as pyrrolidone, N-methylpyrrolidone, ⁇ -caprolactam, N-methyl- ⁇ -caprolactam and N-ethyl- ⁇ -caprolactam.
- lactones such as 4-butyrolactone
- lactams such as pyrrolidone, N-methylpyrrolidone, ⁇ -caprolactam, N-methyl- ⁇ -caprolactam and N-ethyl- ⁇ -caprolactam.
- water-miscible organic solvents which are customary in woodstains can also be used.
- lower alcohols such as ethanol
- ketones such as methyl ethyl ketone
- mono- and polyglycols such as ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol and dipropylene glycol
- carboxamides such as formamide and dimethylformamide
- cyclic ureas such as 1,3-dimethyl-2-imidazolidinone.
- the dyestuffs of the formula (I) are readily water-soluble.
- concentration and stability of the aqueous solutions can also be increased considerably, for example, by addition of a water-miscible organic solvent.
- Possible materials for dyeing are shaped wood in the most diverse forms, including in finely divided form, such as wood shavings and sawdust, but above all wood veneers.
- the veneers are as a rule large-area wooden sheets of various timbers of a thickness of, in general, 0.5 to 10 mm.
- Possible types of wood are pine, spruce, fir, larch, Scots pine, oak, beech, ash, maple, walnut, pear, teak, mahogany, chestnut, birch, hazelnut, linden, willow, poplar or plane.
- the dyestuffs of the formula (I) which can be used according to the invention can be on the surface or inside the wood material to a greater or lesser depth, depending on the nature and type of wood and depending on the dyeing conditions. Veneers are usually dyed as far as possible through the entire cross section.
- the use according to the invention takes place in the customary manner, and the dyestuff preparations are preferably applied to the wood, for example, by brushing, rolling, spraying or impregnation.
- the dyestuff preparations are preferably used in undiluted form, while in the case of impregnation or immersion dyeing, the dyestuff preparations can be diluted with up to 300 times the amount of water.
- a deeper penetration of the dyestuff into the wood material or through-dyeing of a wood veneer is as a rule achieved by immersion dyeing in closed containers.
- the depth of penetration is determined by the treatment time, the temperature of the dyebath and the pressure applied to the container.
- the treatment time can be up to 10 hours, the temperature is as a rule 20 to 120° C. and the pressure is preferably 1 to 2 bar.
- the dyestuffs of the formula (I) are distinguished by a good penetration and as a rule give wood dyeings with an adequate depth of penetration or a complete penetration after just 3 hours at temperatures of up to 100° C.
- the goods to be dyed should be moistened beforehand in order to avoid deformations during the dyeing process. So that the dyestuff is fixed better in the wood, the pH of the dyebath is lowered to 5 to 4.5.
- the dyed material is generally dried in air, either at room temperature or in a circulating air cabinet at higher temperatures, preferably at 40 to 80° C. Weather-resistant dyeings which have wet-fastness properties and have a good fastness to light and overpainting are obtained in this manner using the dyestuffs of the formula (I).
- the dyebath is first heated to 40° C. and the pH of the liquor is lowered to 5.0 with about 1 l of acetic acid 1:1. The dyebath is then heated up to 98° C. at a rate of 1° C. per minute, the temperature is maintained at this level for 1 hour and the dyebath is then allowed to cool to 70° C. After the sheets have been rinsed with cold water and dried in a circulating air cabinet at 80° C., a through-dyed veneer in a lightfast and weatherfast brown shade is obtained.
- the yellow dyestuff of the formula (Ia), the orange dyestuff of the formula (Ib) and the red dyestuff of the formula (Ic) can also be employed in the form of stable liquid formulations or mixtures of these liquid forms.
- a liquor ratio of 1:25 (1 part by weight of wood and 25 parts by weight of liquor) and a dyestuff concentration of 1.5% strength (1.5 parts by weight of pure dyestuff and 100 parts by weight of substrate) coloured veneers in the yellow to red range are obtained.
Abstract
This invention relates to a process for dyeing wood with a liquid dyestuff preparation containing
wherein
n1 and n2 denote the number 1 or 0,
X represents N or CH,
Ct+ represents a cation,
A, B, G, and D are independently a polyvalent heterocyclic or aromatic radical in which the —(CO)n1—O— or —O— are ortho to the respective —N═N— or —N═X—, and
(b) 15 to 90% by weight of an alkoxyalcohol of the formula (II)
R—O—(-Z-O—)n3—H (II)
wherein
R denotes a straight-chain or branched C1-C4-alkyl,
Z denotes a straight-chain or branched C2-C3-alkylene, and
n3 represents 1, 2, or 3, and
(c) 5 to 75% by weight of water.
Description
- The invention relates to the use of liquid dyestuff preparations for dyeing wood.
- Liquid dyestuff preparations for dyeing wood are usually called woodstains. Woodstains are intended not to mask but to emphasize the grain of the wood and its veneers, giving them colour, and therefore comprise only truly dissolved dyestuffs. Solutions of basic or acidic dyestuffs in water or of solvent dyestuffs in organic solvents are known in practice. In addition to these so-called water-based and solvent-based stains, a combination of these two stains became established at the start of the '80s as a further type. These are water-dilutable solutions of organic dyestuffs in mixtures of water and solvent.
- Woodstains are chiefly employed indoors and serve chiefly for decorative purposes. On application with a sponge, brush or a spray gun, they should penetrate as uniformly as possible and as deeply as possible into the wood material and give a uniform dyeing which is fast to light, water and abrasion after drying. It should furthermore also be possible to protect and preserve the stained wood with clear furniture varnishes without the dyestuffs bleeding out into the clear varnish.
- Woodstains chiefly comprise metal complex dyestuffs.
- It has been found that water-dilutable woodstains which meet the requirements in practice in an outstanding manner are provided with the liquid dyestuff preparations described in the following.
- The invention relates to the use of liquid dyestuff preparations for dyeing wood, characterized in that the liquid dyestuff preparations comprising
-
- wherein
- n1 and n2 denote the number 1 or 0,
- X represents N or CH, Ct+ represents a cation
- and the polyvalent radicals A, B, G and D independently of one another represent heterocyclic or aromatic radicals, in particular optionally substituted phenylene and naphthylene radicals, the particular complexing —COO— or —O— group being in the ortho-position relative to the azo and azomethine group (X═CH) respectively,
- 15 to 90% by weight, in particular 15 to 60% by weight, preferably 20 to 90% by weight, more preferred 25 to 60% by weight, of an alkoxy-alcohol of the formula (II)
- R—O—(-Z-O—)n3—H (II)
- wherein
- R denotes a straight-chain or branched C1-C4-alkyl,
- Z denotes a straight-chain or branched C2-C3-alkylene and
- n3 represents 1, 2 or 3, and
- 5 to 75% by weight of water are employed.
- In general, “liquid” is understood as meaning a liquid state at room temperature under normal pressure.
-
- HO—(OC)n2-G-N═X-D-OH (IV),
- wherein a, B, G, D, n1 and n2 have the abovementioned meanings, are employed.
- Preferred dyestuffs of the formula (I) are derived from the following radicals:
-
-
-
-
-
-
- wherein
- A, B, G, D, n1, n2 and Ct+ have the abovementioned meanings, and
- m represents 0 or 1 and
- R represents 4-nitro or 5-chloro, and in the case where m=1, the o-chlorophenylazo group is in the para-position relative to the complexing —O— group.
- Preferred substituents of the polyvalent radicals A, B, G and D are, for example, those chosen from the group consisting of: NO2, halogen, in particular chlorine, sulphonamide and C1-C4-alkyl.
- The dyestuffs of the formula (I) which can be used according to the invention are known in most cases and can be prepared by known methods, such as are described, for example, in EP-A 066 230, EP-A 072 501 or EP-A 532 994.
- The cation represented by Ca+ is preferably an alkali metal cation, in particular a lithium, sodium or potassium cation, an ammonium ion, the cation of an organic amine, such as, for example, that of mono-, di- or triethylamine, mono-, di- or tri-ethanolamine, N-methyldiethanolamine, N-butyldiethanolamine or N,N-diethylethanolamine, or a tetraalkylammonium, such as, for example, tetramethylammonium. A particularly preferred cation is the lithium cation.
-
-
-
-
-
-
- The dyestuffs of the formulae (Ia) to (Ig) wherein Ct+=Li+ are particularly preferred.
- Preferred alkoxy-alcohols of the formula (II) which are mentioned are, for example, the following representatives: C1-C4-monoalkyl ethers of mono- and polyglycols, such as methyl glycol, ethyl glycol, propyl glycol, butyl glycol, methyldiethylene glycol, butyldiethylene glycol, methyltriethylene glycol, 1-methoxy-2-propanol, 2-methoxy-1-propanol, 1-ethoxy-2-propanol, 2-ethoxy-1-propanol, dipropylene glycol monomethyl ether means (3-(3-methoxy-propoxy)-1-propanol) and dipropylene glycol monoethyl ether means (3-(3-ethoxy-1-propoxy)-1-propanol).
- Particularly suitable alkoxy-alcohols of the formula (II) are the C1-C4-monoalkyl ethers of glycols and diglycols and the monoalkyl ethers of 1,2-propylene glycol and of ethylene glycol, in particular monoalkyl ethers of 1,2-propylene glycol. 1-Ethoxy-2-propanol is especially preferred.
- The dyestuff preparations used according to the invention can furthermore comprise
- 0 to 40% by weight, in particular 20 to 35% by weight, of a cyclic ester or amide and
- 0 to 5% by weight of auxiliaries customary in woodstains, such as fungicides, UV stabilizers, binders and/or surfactants.
- Possible preferred cyclic esters or amides are, for example, lactones, such as 4-butyrolactone, and lactams, such as pyrrolidone, N-methylpyrrolidone, ε-caprolactam, N-methyl-ε-caprolactam and N-ethyl-ε-caprolactam.
- Further water-miscible organic solvents which are customary in woodstains can also be used. There may be mentioned here in particular: lower alcohols, such as ethanol, ketones, such as methyl ethyl ketone, mono- and polyglycols, such as ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol and dipropylene glycol, and carboxamides, such as formamide and dimethylformamide, as well as cyclic ureas, such as 1,3-dimethyl-2-imidazolidinone.
- The dyestuffs of the formula (I) are readily water-soluble. The concentration and stability of the aqueous solutions can also be increased considerably, for example, by addition of a water-miscible organic solvent.
- It has been found that concentrated aqueous solutions of these dyestuffs of the formula (I), in particular those of the formulae (II) to (VIII), preferably in a mixture of water and at least one water-miscible organic solvent, are valuable woodstains with which weatherfast and lightfast wood dyeings can be achieved by various methods of application.
- Possible materials for dyeing are shaped wood in the most diverse forms, including in finely divided form, such as wood shavings and sawdust, but above all wood veneers. The veneers are as a rule large-area wooden sheets of various timbers of a thickness of, in general, 0.5 to 10 mm. Possible types of wood are pine, spruce, fir, larch, Scots pine, oak, beech, ash, maple, walnut, pear, teak, mahogany, chestnut, birch, hazelnut, linden, willow, poplar or plane.
- The dyestuffs of the formula (I) which can be used according to the invention can be on the surface or inside the wood material to a greater or lesser depth, depending on the nature and type of wood and depending on the dyeing conditions. Veneers are usually dyed as far as possible through the entire cross section.
- The use according to the invention takes place in the customary manner, and the dyestuff preparations are preferably applied to the wood, for example, by brushing, rolling, spraying or impregnation. In the case of brushing, rolling or spraying, the dyestuff preparations are preferably used in undiluted form, while in the case of impregnation or immersion dyeing, the dyestuff preparations can be diluted with up to 300 times the amount of water.
- A deeper penetration of the dyestuff into the wood material or through-dyeing of a wood veneer is as a rule achieved by immersion dyeing in closed containers. The depth of penetration is determined by the treatment time, the temperature of the dyebath and the pressure applied to the container. The treatment time can be up to 10 hours, the temperature is as a rule 20 to 120° C. and the pressure is preferably 1 to 2 bar.
- The dyestuffs of the formula (I) are distinguished by a good penetration and as a rule give wood dyeings with an adequate depth of penetration or a complete penetration after just 3 hours at temperatures of up to 100° C.
- In the case of immersion dyeing in a closed container, the goods to be dyed should be moistened beforehand in order to avoid deformations during the dyeing process. So that the dyestuff is fixed better in the wood, the pH of the dyebath is lowered to 5 to 4.5. After the treatment, the dyed material is generally dried in air, either at room temperature or in a circulating air cabinet at higher temperatures, preferably at 40 to 80° C. Weather-resistant dyeings which have wet-fastness properties and have a good fastness to light and overpainting are obtained in this manner using the dyestuffs of the formula (I).
- 20 thoroughly moistened wood veneers of maple of the dimensions 2 m×1 m×1 mm are provided with spacers of polyester and transferred to a container which can be closed, and a dye liquor of 3.2 kg of a liquid preparation of the dyestuff of the formula Id and 400 l of water is poured over them. The liquid preparation itself is composed of 13% by weight of dyestuff, 40% by weight of 1-ethoxy-2-propanol and water as the balance.
- The dyebath is first heated to 40° C. and the pH of the liquor is lowered to 5.0 with about 1 l of acetic acid 1:1. The dyebath is then heated up to 98° C. at a rate of 1° C. per minute, the temperature is maintained at this level for 1 hour and the dyebath is then allowed to cool to 70° C. After the sheets have been rinsed with cold water and dried in a circulating air cabinet at 80° C., a through-dyed veneer in a lightfast and weatherfast brown shade is obtained.
- In a manner similar to that in Example 1, commercially available wood veneers are dyed with a mixture of 10 parts of liquid preparation of the black dyestuff of the formula (Ig), 1 part of liquid preparation of the orange dyestuff of the formula (Ib) and 0.5 part of liquid preparation of the brown dyestuff of the formula (Id), the preparation of the black dyestuff also comprising 20% by weight of ε-caprolactam, in addition to 45% by weight of 1-ethoxy-2-propanol. After washing and drying, black veneers with good fastness to light and weather are obtained.
- Instead of the brown dyestuff of the formula (Id), the yellow dyestuff of the formula (Ia), the orange dyestuff of the formula (Ib) and the red dyestuff of the formula (Ic) can also be employed in the form of stable liquid formulations or mixtures of these liquid forms. At a liquor ratio of 1:25 (1 part by weight of wood and 25 parts by weight of liquor) and a dyestuff concentration of 1.5% strength (1.5 parts by weight of pure dyestuff and 100 parts by weight of substrate), coloured veneers in the yellow to red range are obtained.
- Instead of the solvent used in the liquid preparation of the dye according to formula 1d of example 1, also a liquid preparation containing 40% by weight of dipropylene glycol monomethyl ether dyes veneer in a lightfast and weatherfast brown shade.
- Instead of the solvent used in the black liquid preparation in example 2, 45% by weight of dipropylene glycol monomethyl ester are also used to get veneer in a lightfast and weatherfast black shade.
Claims (9)
1. Use of liquid dyestuff preparations for dyeing wood, wherein the liquid dyestuff preparations comprising
5 to 30% by weight, in particular 12 to 23% by weight, of a dyestuff of the formula I
wherein
n1 and n2 denote the number 1 or 0,
X represents N or CH,
Ct+ represents a cation
and the polyvalent radicals A, B, G and D independently of one another represent heterocyclic or aromatic radicals, in particular optionally substituted phenylene and naphthylene radicals, the particular complexing —COO— or —O— group being in the ortho-position relative to the azo and azomethine group (X═CH) respectively,
15 to 90% by weight, in particular 15 to 60% by weight, of an alkoxy-alcohol of the formula (II)
R—O—(-Z-O—)n3—H (II)
wherein
R denotes a straight-chain or branched C1-C4-alkyl,
Z denotes a straight-chain or branched C2-C3-alkylene and
n3 represents 1, 2 or 3, and
5 to 75% by weight of water are employed.
2. Use according to claim 1 , characterized in that the dyestuffs of the formula (I) are derived from the following radicals:
possible radicals of the formula
Possible radicals of the formula —B—OH are, preferably:
Possible radicals of the formula -G-(CO)n2OH are, preferably:
Possible radicals of the formula -D-OH are, preferably:
3. Use according to claim 1 , characterized in that the dyestuffs of the formula (I) employed are those of the formula (V)
wherein
A, B, G, D, n1, n2 and Ca+ have the meanings given in claim 1 , and
m represents 0 or 1 and
R represents 4-nitro or 5-chloro, and in the case where m=1, the o-chlorophenylazo group is in the para-position relative to the complexing —O— group.
5. Use according to claim 1 , characterized in that at least one of the following compounds is employed as the alkoxy-alcohol of the formula (II): C1-C4-monoalkyl ethers of mono- and polyglycols, such as methyl glycol, ethyl glycol, propyl glycol, butyl glycol, methyldiethylene glycol, butyl-diethylene glycol, methyltriethylene glycol, 1-methoxy-2-propanol, 2-methoxy-1-propanol, 1-ethoxy-2-propanol, 2-ethoxy-1-propanol, dipropylene glycol monomethyl ether means (3-(3-methoxy-propoxy)-1-propanol) or dipropylene glycol monoethyl ether means (3-(3-ethoxy-1-propoxy)-1-propanol).
6. Use according to claim 1 , characterized in that the liquid dyestuff preparation furthermore comprises
0 to 40% by weight, in particular 20 to 35% by weight, of a cyclic ester or amide and
0 to 5% by weight of auxiliaries customary in woodstains.
7. Use according to claim 1 , wherein the liquid preparation comprises
20 to 90% by weight, in particular 25 to 60% by weight of an alkoxy-alcohol of the formula II wherein n3 represents 2 or 3 is employed.
8. Use according to claim 1 , for dyeing wood, characterized in that the possible types of wood are the following: pine, spruce, fir, larch, Scots pine, oak, beech, ash, maple, walnut, pear, teak, mahogany, chestnut, birch, hazelnut, linden, willow, poplar or plane.
9. Process for dyeing wood, characterized in that the dyestuff preparations according to claim 1 are applied to the wood by brushing, rolling, spraying, impregnating or immersion, if appropriate after 300-fold dilution with water.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19905279.4 | 1999-02-09 | ||
DE19905279A DE19905279A1 (en) | 1999-02-09 | 1999-02-09 | Use of liquid dye preparations for coloring wood |
Publications (1)
Publication Number | Publication Date |
---|---|
US20020038482A1 true US20020038482A1 (en) | 2002-04-04 |
Family
ID=7896904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/497,008 Abandoned US20020038482A1 (en) | 1999-02-09 | 2000-02-02 | Use of liquid dyestuff preparations for dyeing wood |
Country Status (3)
Country | Link |
---|---|
US (1) | US20020038482A1 (en) |
EP (1) | EP1027968A3 (en) |
DE (1) | DE19905279A1 (en) |
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US20060167508A1 (en) * | 2005-01-21 | 2006-07-27 | Willem Boute | Implantable medical device with ventricular pacing protocol including progressive conduction search |
US20070203523A1 (en) * | 2006-02-28 | 2007-08-30 | Betzold Robert A | Implantable medical device with adaptive operation |
US20070219589A1 (en) * | 2006-01-20 | 2007-09-20 | Condie Catherine R | System and method of using AV conduction timing |
US20070293899A1 (en) * | 2006-06-15 | 2007-12-20 | Sheldon Todd J | System and Method for Ventricular Interval Smoothing Following a Premature Ventricular Contraction |
US20070293897A1 (en) * | 2006-06-15 | 2007-12-20 | Sheldon Todd J | System and Method for Promoting Instrinsic Conduction Through Atrial Timing Modification and Calculation of Timing Parameters |
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US20070293900A1 (en) * | 2006-06-15 | 2007-12-20 | Sheldon Todd J | System and Method for Promoting Intrinsic Conduction Through Atrial Timing |
US20070299478A1 (en) * | 2004-10-25 | 2007-12-27 | Casavant David A | Self Limited Rate Response |
US20080027490A1 (en) * | 2006-07-31 | 2008-01-31 | Sheldon Todd J | Pacing Mode Event Classification with Rate Smoothing and Increased Ventricular Sensing |
US20080027493A1 (en) * | 2006-07-31 | 2008-01-31 | Sheldon Todd J | System and Method for Improving Ventricular Sensing |
US20080027492A1 (en) * | 2006-07-31 | 2008-01-31 | Sheldon Todd J | Rate Smoothing Pacing Modality with Increased Ventricular Sensing |
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US20100222839A1 (en) * | 2009-02-27 | 2010-09-02 | Medtronic, Inc. | System and method for conditional biventricular pacing |
US20100222838A1 (en) * | 2009-02-27 | 2010-09-02 | Sweeney Michael O | System and method for conditional biventricular pacing |
US20100222834A1 (en) * | 2009-02-27 | 2010-09-02 | Sweeney Michael O | System and method for conditional biventricular pacing |
US7856269B2 (en) | 2006-07-31 | 2010-12-21 | Medtronic, Inc. | System and method for determining phsyiologic events during pacing mode operation |
US20110014414A1 (en) * | 2009-11-06 | 2011-01-20 | Green Rev LLC | Sustainable simulated commodity tropical hardwood panel |
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US7294730B2 (en) * | 2005-11-30 | 2007-11-13 | Xerox Corporation | Colorant compounds |
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DE1901255A1 (en) * | 1969-01-11 | 1970-08-06 | Basf Ag | Wood staining with dyes and solvents to pro - duce tone continuity and depth |
DE2605574C2 (en) * | 1976-02-12 | 1984-01-12 | Bayer Ag, 5090 Leverkusen | Process for the production of chromium and cobalt complex dyes and their solutions |
DE2634512C2 (en) * | 1976-07-31 | 1984-11-08 | Basf Ag, 6700 Ludwigshafen | Process for the production of concentrated, low-salt solutions of sulfonic acid group-free cobalt and chromium 1 to 2 complex dyes |
DE2918634A1 (en) * | 1979-05-09 | 1980-11-20 | Basf Ag | METHOD FOR THE PRODUCTION OF COBALT AND CHROME 1 TO 2 COMPLEX DYES |
DE3121923A1 (en) * | 1981-06-02 | 1982-12-16 | Bayer Ag, 5090 Leverkusen | ASYMMETRIC 1: 2 CHROME COMPLEX DYES |
DE3132334A1 (en) * | 1981-08-17 | 1983-03-03 | Bayer Ag, 5090 Leverkusen | ASYMMETRICAL 1: 2 CHROME COMPLEX DYES |
CH660599A5 (en) * | 1984-07-26 | 1987-05-15 | Ciba Geigy Ag | ANIONIC DYE SOLUTIONS. |
DE4137851A1 (en) * | 1991-11-16 | 1993-05-19 | Basf Ag | METHOD FOR ADDING WOODEN FORMATION |
-
1999
- 1999-02-09 DE DE19905279A patent/DE19905279A1/en not_active Withdrawn
-
2000
- 2000-01-27 EP EP00101606A patent/EP1027968A3/en not_active Withdrawn
- 2000-02-02 US US09/497,008 patent/US20020038482A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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EP1027968A2 (en) | 2000-08-16 |
DE19905279A1 (en) | 2000-08-10 |
EP1027968A3 (en) | 2002-09-18 |
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