US3069219A - Colouring cellulose triacetate textile materials - Google Patents
Colouring cellulose triacetate textile materials Download PDFInfo
- Publication number
- US3069219A US3069219A US593036A US59303656A US3069219A US 3069219 A US3069219 A US 3069219A US 593036 A US593036 A US 593036A US 59303656 A US59303656 A US 59303656A US 3069219 A US3069219 A US 3069219A
- Authority
- US
- United States
- Prior art keywords
- cellulose triacetate
- bath
- coupling component
- acid
- aqueous
- 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.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title claims description 46
- 229920002284 Cellulose triacetate Polymers 0.000 title claims description 37
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 title claims description 37
- 239000004753 textile Substances 0.000 title description 25
- 238000004040 coloring Methods 0.000 title description 8
- 230000008878 coupling Effects 0.000 claims description 47
- 238000010168 coupling process Methods 0.000 claims description 47
- 238000005859 coupling reaction Methods 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 28
- 238000006149 azo coupling reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002895 organic esters Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000011282 treatment Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 15
- 229940081735 acetylcellulose Drugs 0.000 description 15
- 229920002301 cellulose acetate Polymers 0.000 description 15
- 239000002585 base Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 9
- 150000008049 diazo compounds Chemical class 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- -1 methyl benzoate Chemical class 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000000549 coloured material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 2
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000001112 coagulating effect Effects 0.000 description 2
- 238000012505 colouration Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 2
- 238000000578 dry spinning Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- JSCNDCWUFHAJQL-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(O)C(C(=O)O)=C2 JSCNDCWUFHAJQL-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- WBGVVXSCGNGJFL-UHFFFAOYSA-N 3-amino-n,n-diethyl-4-methoxybenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(N)=C1 WBGVVXSCGNGJFL-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
- MLQLFEBDEPZXFY-UHFFFAOYSA-M 5-chloro-2-methoxybenzenediazonium;chloride Chemical compound [Cl-].COC1=CC=C(Cl)C=C1[N+]#N MLQLFEBDEPZXFY-UHFFFAOYSA-M 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical compound O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 244000053634 jackwood Species 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical class CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/928—Solvents other than hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/40—Cellulose acetate
- D06P3/46—Cellulose triacetate
- D06P3/50—Preparing azo dyes on the material
Definitions
- Cellulose acetate of acetyl value above 59% is hereinafter referred to as cellulose triacetate.
- azo dyes thereon from diazotisable amino compounds and certain coupling components, notably arylamides of.2:3-hydroxynaphthoic acids and some other ortho-hydroxy caboxylic acids, e.g. 2-hydroxy-carbazole-3-carboxylic' acid and 3-hydroxydiphenylene oxide-Z-carboxylic acid.
- Further coupling components which can be used for this purpose include arylamides and certain other amides of aceto-acetic acid and other beta-ketocarboxylic acids; these latter compounds are capable of yielding yellow shades with appropriate diazo compounds.
- the foregoing coupling components are characterised by yielding with simple diazo compounds, e.g. diazotised aniline or diazotised para-nitroaniline or parachloraniline, azo dyes which are insoluble in water. Further, these water-insoluble azo dyes are such. as exhibit substantially no aflinity for textile material of acetone-soluble cellulose acetate when applied to the latter in the form of simple aqueous dispersions.
- simple diazo compounds e.g. diazotised aniline or diazotised para-nitroaniline or parachloraniline
- azo dyes which are insoluble in water.
- these water-insoluble azo dyes are such. as exhibit substantially no aflinity for textile material of acetone-soluble cellulose acetate when applied to the latter in the form of simple aqueous dispersions.
- the material is allowed to take-up the coupling component from an aqueous dispersion of the latter, particularly a neutral or slightly acid or slightly alkaline dispersions. Further, it is desirable that both the diazotisable base and following which the material is preferably given an alkaline treatment, for example, treatment in a soap bath containing alkali.
- the amount of the naphthol taken up is roughly double that taken up in the absence of the diethyl phthalate, other conditions being the same. Similar, though rather less marked improvement in take-up of Naphthol AS/BG is observed if the cellulose triacetate is first treated with an aqueous dispersion of the diethyl phthalate and then with an aqueous dispersion of the. Naphthol AS/BG.
- the diethyl phthalate or other substantially water-insoluble organic compounds are compatible with and may even be solvents for the cellulose triacetate they are taken up by the latter from the aqueous bath; in other words they have substantive afiinity for the cellulose triacetate.
- the present invention particularly contemplates the incorporation in cellulose triacetate textile material of an azo coupling component of the kind indicated above by a process in which the fibre is permitted to take-up the coupling component from an equeous bath in the presence of diethyl phthalate or other water-insoluble substance of the kind indicated above, the latter being present in the bath or already in the fibre.
- the invention also includes the conversion of a coupling component so incorporated into the material, into an azo dye by couplingwith a diazo compound and particularly with a diazo compound formed by diazotising a diazotisable base present in the fibre with the coupling component.
- the base may be incorporated from the same bath as, and either simultaneously with or separately from the coupling component, or from a separate bath.
- the amount of the water-insoluble organic substance in the bath may be for example from 10 to 40% based on the weight of the cellulose triacetate.
- diethyl phthalate is particularly suitable for the purposes of the invention but many other substances, particularly liquids, may be employed.
- any of the substantially water-insoluble assistants prescribed in United States application S. No. 472,- 758 filed Dec. 2, 1954, now U.S. Patent No. 2,982,597 for assisting the incorporation of disperse dyes in cel lulose triacetate textile material.
- esters of phthalic acid e.g. dimethyl phthalate or dipropyl phthalate
- esters of benzene monocarboxylic acids e.g. methyl benzoate
- methyl salicylate trialkyl phosphates e.g.
- tripropyl or tributyl phosphates or tri-beta-chlorethyl phosphate and chlorobenzene All these have substantive atfinity for cellulose triacetate and are taken up by the latter from aqueous dis"- persions of them.
- Aqueous baths containing the organic substance or
- a dispersing agent may be of anionic character, e.g. Turkey red oil or a dispersing agent of the higher fatty alcohol sulphate or alkylaryl-sulphonate type. Again, it may be a non-ionic dispersing agent, e.g. of the kind obtainable by condensing a higher fatty alcohol or a higher fatty acid or castor oil with ethylene oxide in proportion sufllcient to render the reaction product water-soluble.
- the dispersing agent serves to maintain the organic substance and/or the cou pling component in a state of dispersion.
- the new process is of particular value, especially if full shades are required, when the coupling component is the 4-methoxyanilide, the 2:5-dimethoxyanilide, or the 2'-methyl-4'-methoxyanilide of 2:3-hydroxynaphthoic acid, or di-(acetoacetyl)-ortho-tolidine, or the 2:5'-dimethoxyanilide of 3-hydroxy-diphenylene oxide-2- carboxylic acid.
- the take-up of these coupling components by cellulose triacetate from aqueous dispersions is very greatly increased by the diethyl phthalate or similar substance. In the absence of the latter the take-up is insufficient to permit full shades to be obtained.
- the diazotisable bases which may be employed include 4-chloro-2-amino-l-methyl-benzene, 2:5 dichloroaniline, 2-chloraniline, 4-nitro-aniline, 5-nitro-2-amino-l-methylbenzene, 4-chloro-2-amino-l-methoxy-benzene, S-nitro- 2 amino-l-methoxy-benzene, 2 amino-l-methoxy benzene-4-sulphonic acid diethylamide, 2-amino-1-methoxybenzene-4-ethylsulphone, 2:5-diethoxy-4-benzoyl aminoaniline, amino-azo-toluene, 4-aminobenzene-azo-4'-arnino-2'-acetylamino-5'-methoxy-benzene (424' diamino-2'- acetylamino-S-methoxy-azobenzene), amino aZo-cresolmethylether (2 5-dimeth
- the aqueous baths from which the coupling components are applied may be neutral, slightly acid, or slightly alkaline; for example they may have a pH value of 6 to 8.
- the aqueous bath may be prepared by dissolving the coupling component in about the minimum necessary amount of aqueous caustic soda and adding the resulting solution to the necessary amount of water containing a suitable dispersing agent.
- the pH value of the bath may then be adjusted to the desired value, e.g. pH 7 to 7.5, by addition of acid, for instance formic or acetic acid.
- the diethyl phthalate or other assistant employed is preferably first converted into a concentrated emulsion by mixing with a dispersing agent and with a little water and the emulsion likewise added to the bath.
- the alkalinity of the bath will usually be rapidly reduced by the ester, the latter being hydrolysed in the process.
- the diazotisable amino compound in the same bath.
- the baths are preferably employed at relatively high temperatures, for example to 98 or 100 C.
- diazotisable amine Following the incorporation of the coupling component and diazotisable amine in the cellulose triacetate material, the latter is, as indicated above, subjected to treatment to diazotise the amine and effect coupling of the resulting diazo compound with the coupling component.
- This diazotisation may be effected by means of a nitrous acid bath and particularly by means of an aqueous bath prepared with sodium nitrite and an acid, e.g. a mineral acid such as hydrochloric acid or an organic acid such as acetic or formic acid. Diazotisation may be effected at ordinary temperatures or at rather higher temperature, e.g. temperatures up to 4050 C.
- the material is preferably given a mild alkaline treatment for example treatment in a bath containing soap or other detergent together with an alkali e.g. sodium carbonate.
- This soaping treatment may be effected or completed at 70 to 85 C. or higher e.g. at 95l00 C.
- the materials coloured by the new process are, in general of very good resistance to hot soaping treatments, but under these conditions a certain amount of staining of any white cellulose acetate material in contact with the coloured material during the hot soaping treatment may be evidenced. This is possibly due to the coloured material containing small amounts of the original base or of decomposition products of its diazo compound.
- a mild reducing treatment particularly treatment with a hot acidified aqueous solution of a formaldehyde sulphoxylate.
- Such a treatment may comprise for instance, subjecting the material for 1 hour at 75 C. to an aqueous bath prepared with 1 g.p.l. of Adinol T (sodium oleyl taurine), 1 cc. per 1. of acetic acid and 0.5 g.p.l. of sodium formaldehyde sulphoxylate.
- Example 1 A treatment bath is made up from the following:
- the bath is prepared as follows:
- the base is pasted with 10 g. of the Lissapol C and brought to the boil with a little water, the resulting dispersion being then added to the main body of water.
- the naphthol is pasted with a little Water, a solution of the caustic'soda in a little water added and the mixture warmed until the naphthol is dissolved; the solution is then added to the main body of water.
- the diethyl phthalate is emulsified with the remaining Lissapol C and a little water in a mechanical emulsifier and the resulting emulsion likewise added to the main body of water.
- Example 3 v A treatment bath is made up from the following:
- water 40 g. Lissapol C -30 g. 4 aminobenzeneazo-4'-amino-2'-acetylamino-5-methoxybenzene 50 g. Naphthol AS/ LT 16.6 g. caustic soda flakes 200 g. diethyl phthalate.
- Thepreparation of the bath is effected in the manner described in Example 1. 1 kg.,of a fabric of cellulose triacetate yarn is then processed in this. bath in the manner described in Example 1 and then diazotised and further treated as described in that example. A full black shade is obtained.
- Example 4 A fabric of cellulose triacetate yarn is dyed in the manner described in Example 3 except that, before additionof the emulsified diethyl phthalate, the bath is brought to pH 7.0-7.5 by addition of dilute acetic acid.
- Example 5 A treatment bath is prepared from the following:
- Lissapol C sodium oleyl sulphate
- amino-a20-cresol-methyl-ether 30 g. NaphtholAS/ DB 20 g. caustic soda flakes 150 g diethyl phthalat 30 1. water.
- Y Lissapol C (sodium oleyl sulphate) 14 g. amino-a20-cresol-methyl-ether 30 g. NaphtholAS/ DB 20 g. caustic soda flakes 150 g diethyl phthalat 30 1. water.
- the preparation of the bath is effected as in Example a 30 1.
- the fabric is entered at 20 C. and the temperature raised to 45 C. in 30 minutes, being maintained at this for a further 30 minutes.
- Example 6 A treatment bath is made up from thefollowing:
- the bath is prepared in the manner described in Example 1 except that the pH value is adjusted to 7.0-7.5 by addition of dilute acetic acid before adding the emulsified diethyl phthalate.
- a treatment bath is prepared from the following:
- Example 8 q A treatment bath is prepared from the following:
- water 40 g. Lissapol C 10 g. Fast Red GG Base (para nitro aniline) 10 g. Naphthol AS/G 3.3 g. Caustic soda flakes 200 g. diethyl phthalate.
- the bath is prepared in the manner described in Example 1 except that the pH value is adjusted to 7.0-7.5 by addition of dilute acetic acid before adding the emulsified diethyl phthalate.
- the :diethyl phthalate may be replaced by tri-n-propylphosphate with similar results.
- Textile fibres of high acetyl cellulose acetate to be coloured in accordance with the invention may be those made by a melt spinning process, especially a process described in United States applications S. Nos. 243,994 filed August 28, 1951, now abandoned, 292,772 filed June 10, 1952, now U.S. Patent No. 2,888,711, 304,441 filed August 14, 1952, now abandoned, 338,834 filed Feb. 2 5, 1953, now US. Patent No. 2,982,597, or 423,743 filed April 16, 1954, now abandoned.
- a powdered cellulose ester is urged (e. g.
- the spinning orifices may be circular, or they may be in the form of slits or of two or more closely spaced orintersecting holes, as described in United States application 8. No. 338,834.
- cellulose triacetate in the form of a coherent rod or a block or tablet of uniform cross-section is pressed axially against a heated plate having spinning orifices therein.
- solutions of high acetyl cellulose acetate in mixtures of methylene or ethylene chloride with methyl or ethyl alcohol or acetic acid, or in acetic acid alone, may be extruded as filaments and set either by means of a coagulating liquid or by an evaporative method.
- solutions of cellulose triacetate in mixtures of methylene or ethylene chloride with acetic acid may be extruded into a coagulating liquid comprising an aqueous alcohol, especially aqueous ethyl alcohol of concentration about 90-95%, as described in United States Patent No.
- 2,657,973 or solutions in acetic acid may be extruded into aqueous acetic acid which may with advantage contain a fairly high proportion of ammonium or an alkali metal acetate, an alkaline earth metal acetate or magnesium acetate, or of some other salt.
- Yet another method by which textile fibres of cellulose acetate of high acetyl value may be obtained is the further acetylation of a textile material of cellulose acetate of lower acetyl value.
- yarns or fabrics of acetone-soluble cellulose acetate may be further acetylated with acetic anhydride in the the presence of a diluent such as benzene, and of a basic or acid esterification catalyst such as pyridine, sulphuric acid, perchloric acid or hydrochloric acid, with or without a metal chloride such as zinc chloride or ferric chloride as described in United States Patents Nos. 2,159,011 and 2,159,012.
- the fibres of high acetyl cellulose acetate may be those having a high safe ironing such as are described, together with processes for their manufacture, in United States application S. No. 400,798 filed Dec. 28, 1953 now US. Patent No. 2,862,785.
- the materials may, after colouring, be given a treatment such as is described in that application.
- the cellulose triacetate yarn of the fabric coloured according to the examples is a product made by dry-spinning a solution of cellulose acetate of about 61% acetyl value in a mixture of methylene chloride and methyl alcohol (ratio about 93:7 by volume).
- Method of incorporating an enolic azo coupling component in a cellulose triacetate textile material which comprises allowing the material to take up the coupling component from an aqueous bath having dispersed therein both the coupling component and an assistant consisting essentially of a substantially water-insoluble oxygen containing organic ester which is a solvent for the coupling component and which has a substantive afiinity for the cellulose triacetate.
- substantially water-insoluble organic substance is diethyl phthalate present to the extent of from -40% based on the weight of the textile materials.
- Method of incorporating an enolic azo coupling component in a cellulose triacetate textile material which comprises allowing the material to take up the coupling component from an aqueous bath at a temperature of 95 to 100 C. and having dispersed therein both the coupling component and from 1040% of diethyl phthalate based on the weight of the textile material.
- a method of colouring textile material of cellulose triacetate which comprises allowing the material to take up an enolic azo coupling component and a diazotisable base from an aqueous bath having dispersed therein the coupling component, the base, and an assistant consisting essentially of from 1040% based on the weight of the textile material of a substantially water-insoluble organic substance which is a solvent for the coupling component and which has a substantive afiinity for the cellulose triacetate, and thereafter treating the material to effect diazotisation of the base and coupling of the resulting diazo compound with the coupling component on the material.
- a method of colouring cellulose triacetate textile material which comprises allowing the material to take up an enolic azo coupling component and a diazotisable base from an aqueous bath having dispersed therein the coupling component, the base and from 10-40%, based on the weight of the textile material, of diethyl phthalate, and thereafter treating the material to effect diazotisation of the base and coupling of the resulting diazo compound with the coupling component on the material.
- Method of incorporating an enolic azo coupling component in a cellulose triacetate textile material which comprises allowing the material to take up the coupling component from an aqueous bath having dispersed therein both the coupling component and from 10-40%, based on the weight of the textile material, of an assistant consisting essentially of a substantially water-insoluble organic substance which is a solvent for the coupling component and which has a substantive affinity for the cellulose triacetate.
Description
United States Patent Cffifice 3,069,219 Patented Dec. 18, 1962 3,069,219 COLOURING CELLULOSE TRIACETATE TEXTILE MATERIALS Henry Charles Olpin, Jack Wood, and William James Savory, Spondon, near Derby, England, assignors to British Celanese Limited, a company of Great Britain No Drawing. Filed June 22, 1956, Ser. No. 593,036 Claims priority, application Great Britain July 8, 1955 13 Claims. (Cl. 8-48) This invention relates to the colouration of textile material of cellulose acetate of high acetyl value by the formation of azo dyes thereon. The invention is particularly concerned with the colouration of textile material of cellulose acetate having an acetyl value above 59%.
Cellulose acetate of acetyl value above 59% is hereinafter referred to as cellulose triacetate.
It is well known that a wide range of shades of good fastness properties, particularly to washing, can be obtained on cellulose textiles by forming azo dyes thereon from diazotisable amino compounds and certain coupling components, notably arylamides of.2:3-hydroxynaphthoic acids and some other ortho-hydroxy caboxylic acids, e.g. 2-hydroxy-carbazole-3-carboxylic' acid and 3-hydroxydiphenylene oxide-Z-carboxylic acid. Further coupling components which can be used for this purpose include arylamides and certain other amides of aceto-acetic acid and other beta-ketocarboxylic acids; these latter compounds are capable of yielding yellow shades with appropriate diazo compounds. All of the foregoing types of coupling components are commonly referred to as naphthols by reason of the fact that they are employed for colouring textile materials in much the same way as beta-naphthol was very extensively employed. It will be noted, however, that they are not all derivatives of betanaphthol though this is true ofvthe arylamides of 2:3- hydroxynaphthoic acid. They are, however, like betanaphthol and the aforesaid arylamides, characterised by being able to couple with diazo compounds at a carbon atom adjacent to a carbon atom carrying a hydroxy group and for this reason all are often referred to as enolic coupling components. The arylamides of betaketocarboxylic acids contain the group -CH CO- which can be written as CH=C(OH)-; hence there is a justification for describing these compounds also as enolic coupling components.
The foregoing coupling components are characterised by yielding with simple diazo compounds, e.g. diazotised aniline or diazotised para-nitroaniline or parachloraniline, azo dyes which are insoluble in water. Further, these water-insoluble azo dyes are such. as exhibit substantially no aflinity for textile material of acetone-soluble cellulose acetate when applied to the latter in the form of simple aqueous dispersions.
It is further known that, providing a suitable technique is followed, it is possible to use many of the same azo dye components for colouring cellulose acetatetextile material. For the latter purpose, the material is allowed to take-up the coupling component from an aqueous dispersion of the latter, particularly a neutral or slightly acid or slightly alkaline dispersions. Further, it is desirable that both the diazotisable base and following which the material is preferably given an alkaline treatment, for example, treatment in a soap bath containing alkali.
In attempting to apply such methods to the colouring of cellulose triacetate textile materials we have found that the foregoing coupling components are taken up much less readily and/or to a less extent than is the case with ordinary acetone-soluble cellulose acetate materials and that in consequence the coupling component employed is, as a rule, very incompletely utilised and only pale shades obtained.
We have now found that the uptake of enolic coupling components by cellulose triacetate from aqueous baths can be greatly facilitated by means of substantially waterinsoluble organic substances, particularly such as are solvents for the coupling component and compatible with or even solvents for the cellulose triacetate. We have found that diethyl phthalate is a particularly useful and valuable substance for this purpose. Thus, if cellulose triacetate textile material is treated for 1 hour at 98-100 C. in a neutral 40:1 bath having dispersed therein 2% of Naphthol AS/BG (based on the weight of the cellulose triacetate) and 4 g.p.l. of diethyl phthalate, the amount of the naphthol taken up is roughly double that taken up in the absence of the diethyl phthalate, other conditions being the same. Similar, though rather less marked improvement in take-up of Naphthol AS/BG is observed if the cellulose triacetate is first treated with an aqueous dispersion of the diethyl phthalate and then with an aqueous dispersion of the. Naphthol AS/BG. As the diethyl phthalate or other substantially water-insoluble organic compounds are compatible with and may even be solvents for the cellulose triacetate they are taken up by the latter from the aqueous bath; in other words they have substantive afiinity for the cellulose triacetate.
The present invention particularly contemplates the incorporation in cellulose triacetate textile material of an azo coupling component of the kind indicated above by a process in which the fibre is permitted to take-up the coupling component from an equeous bath in the presence of diethyl phthalate or other water-insoluble substance of the kind indicated above, the latter being present in the bath or already in the fibre. The invention also includes the conversion of a coupling component so incorporated into the material, into an azo dye by couplingwith a diazo compound and particularly with a diazo compound formed by diazotising a diazotisable base present in the fibre with the coupling component. The base may be incorporated from the same bath as, and either simultaneously with or separately from the coupling component, or from a separate bath. The amount of the water-insoluble organic substance in the bath may be for example from 10 to 40% based on the weight of the cellulose triacetate.
As already indicated diethyl phthalate is particularly suitable for the purposes of the invention but many other substances, particularly liquids, may be employed. For example any of the substantially water-insoluble assistants prescribed in United States application S. No. 472,- 758 filed Dec. 2, 1954, now U.S. Patent No. 2,982,597, for assisting the incorporation of disperse dyes in cel lulose triacetate textile material.. There may be used for instance other esters of phthalic acid, e.g. dimethyl phthalate or dipropyl phthalate, esters of benzene monocarboxylic acids, e.g. methyl benzoate, or methyl salicylate, trialkyl phosphates e.g. tripropyl or tributyl phosphates or tri-beta-chlorethyl phosphate and chlorobenzene. All these have substantive atfinity for cellulose triacetate and are taken up by the latter from aqueous dis"- persions of them.
Aqueous baths containing the organic substance, or
I both the organic substance and the coupling component;
preferably also contain a dispersing agent. The latter may be of anionic character, e.g. Turkey red oil or a dispersing agent of the higher fatty alcohol sulphate or alkylaryl-sulphonate type. Again, it may be a non-ionic dispersing agent, e.g. of the kind obtainable by condensing a higher fatty alcohol or a higher fatty acid or castor oil with ethylene oxide in proportion sufllcient to render the reaction product water-soluble. The dispersing agent serves to maintain the organic substance and/or the cou pling component in a state of dispersion.
The following coupling components may be incorporated by the new process:
The new process is of particular value, especially if full shades are required, when the coupling component is the 4-methoxyanilide, the 2:5-dimethoxyanilide, or the 2'-methyl-4'-methoxyanilide of 2:3-hydroxynaphthoic acid, or di-(acetoacetyl)-ortho-tolidine, or the 2:5'-dimethoxyanilide of 3-hydroxy-diphenylene oxide-2- carboxylic acid. The take-up of these coupling components by cellulose triacetate from aqueous dispersions is very greatly increased by the diethyl phthalate or similar substance. In the absence of the latter the take-up is insufficient to permit full shades to be obtained.
The diazotisable bases which may be employed include 4-chloro-2-amino-l-methyl-benzene, 2:5 dichloroaniline, 2-chloraniline, 4-nitro-aniline, 5-nitro-2-amino-l-methylbenzene, 4-chloro-2-amino-l-methoxy-benzene, S-nitro- 2 amino-l-methoxy-benzene, 2 amino-l-methoxy benzene-4-sulphonic acid diethylamide, 2-amino-1-methoxybenzene-4-ethylsulphone, 2:5-diethoxy-4-benzoyl aminoaniline, amino-azo-toluene, 4-aminobenzene-azo-4'-arnino-2'-acetylamino-5'-methoxy-benzene (424' diamino-2'- acetylamino-S-methoxy-azobenzene), amino aZo-cresolmethylether (2 5-dimethoxy-2 5 -dimethyl-4-amino-azobenzene) and 2:2'z5 :5 -tetramethoxy-4-amino-azo-benzene. By using a combination of 3-hydroxy-diphenyleneoxide-2-carboxylic acid 2:5'-dimethoxyanilide with amino-azo-cresol-methyl-ether a valuable nigger brown shade having a light fastness of 6 can be obtained, While a black-brown shade can be obtained from the same coupling component and 2:2:5:5'-tetramethoxy-4-aminoazobenzene.
The aqueous baths from which the coupling components are applied may be neutral, slightly acid, or slightly alkaline; for example they may have a pH value of 6 to 8. The aqueous bath may be prepared by dissolving the coupling component in about the minimum necessary amount of aqueous caustic soda and adding the resulting solution to the necessary amount of water containing a suitable dispersing agent. The pH value of the bath may then be adjusted to the desired value, e.g. pH 7 to 7.5, by addition of acid, for instance formic or acetic acid. The diethyl phthalate or other assistant employed is preferably first converted into a concentrated emulsion by mixing with a dispersing agent and with a little water and the emulsion likewise added to the bath. 'If the bath is alkaline, saypH 9 to 12, at the time of adding the assistant and the latter is diethylphthalate or other hydrolysable ester the alkalinity of the bath will usually be rapidly reduced by the ester, the latter being hydrolysed in the process. As already indicated, it is convenient to include the diazotisable amino compound in the same bath. The baths are preferably employed at relatively high temperatures, for example to 98 or 100 C.
Following the incorporation of the coupling component and diazotisable amine in the cellulose triacetate material, the latter is, as indicated above, subjected to treatment to diazotise the amine and effect coupling of the resulting diazo compound with the coupling component. This diazotisation may be effected by means of a nitrous acid bath and particularly by means of an aqueous bath prepared with sodium nitrite and an acid, e.g. a mineral acid such as hydrochloric acid or an organic acid such as acetic or formic acid. Diazotisation may be effected at ordinary temperatures or at rather higher temperature, e.g. temperatures up to 4050 C. Following the diazotisation treatment the material is preferably given a mild alkaline treatment for example treatment in a bath containing soap or other detergent together with an alkali e.g. sodium carbonate. This soaping treatment may be effected or completed at 70 to 85 C. or higher e.g. at 95l00 C.
The materials coloured by the new process are, in general of very good resistance to hot soaping treatments, but under these conditions a certain amount of staining of any white cellulose acetate material in contact with the coloured material during the hot soaping treatment may be evidenced. This is possibly due to the coloured material containing small amounts of the original base or of decomposition products of its diazo compound. We have found that any such tendency to stain white cellulose acetate may be substantially reduced or entirely eliminated by subjecting the coloured material to a mild reducing treatment, particularly treatment with a hot acidified aqueous solution of a formaldehyde sulphoxylate. Such a treatment may comprise for instance, subjecting the material for 1 hour at 75 C. to an aqueous bath prepared with 1 g.p.l. of Adinol T (sodium oleyl taurine), 1 cc. per 1. of acetic acid and 0.5 g.p.l. of sodium formaldehyde sulphoxylate.
The invention is illustrated by the following examples:
Example 1 A treatment bath is made up from the following:
401. water 40 g. Lissapol C (sodium oleyl sulphate) 25 g. I*;ast Red B Base (5-nitro-2-amino-l-methoxy-benzene 50 g. Naphthol AS/ LB 33.3 g. caustic soda flakes 200 g. diethyl phthalate.
The bath is prepared as follows:
The base is pasted with 10 g. of the Lissapol C and brought to the boil with a little water, the resulting dispersion being then added to the main body of water. The naphthol is pasted with a little Water, a solution of the caustic'soda in a little water added and the mixture warmed until the naphthol is dissolved; the solution is then added to the main body of water. The diethyl phthalate is emulsified with the remaining Lissapol C and a little water in a mechanical emulsifier and the resulting emulsion likewise added to the main body of water.
1 kg. of a fabric of cellulose triacetate yarn is entered into the foregoing treatment bath, the latter being at 50 C. The temperature is raised to 95-98 C. in the course of 30 mins, and the processing of the material continued for a further 2 hours at this temperature. The material is then washed off and introduced into 40 litres of water to which have been added 320 mls. of glacial acetic acid and g. of sodium nitrite. Treatment is A fabric of cellulose triacetate yarn is dyed in the manner described in Example 1, except that, before addition of the emulsified diethyl phthalate, the bath is brought to pH 7.0-7.5 by addition of dilute acetic acid.
Example 3 v A treatment bath is made up from the following:
40 1. water 40 g. Lissapol C -30 g. 4 aminobenzeneazo-4'-amino-2'-acetylamino-5-methoxybenzene 50 g. Naphthol AS/ LT 16.6 g. caustic soda flakes 200 g. diethyl phthalate.
Thepreparation of the bath is effected in the manner described in Example 1. 1 kg.,of a fabric of cellulose triacetate yarn is then processed in this. bath in the manner described in Example 1 and then diazotised and further treated as described in that example. A full black shade is obtained.
Example 4 A fabric of cellulose triacetate yarn is dyed in the manner described in Example 3 except that, before additionof the emulsified diethyl phthalate, the bath is brought to pH 7.0-7.5 by addition of dilute acetic acid.
Example 5 A treatment bath is prepared from the following:
30 g. Lissapol C (sodium oleyl sulphate) 14 g. amino-a20-cresol-methyl-ether 30 g. NaphtholAS/ DB 20 g. caustic soda flakes 150 g diethyl phthalat 30 1. water. Y
The preparation of the bath is effected as in Example a 30 1. water 240 ml. glacial acetic acid 120 g. sodium nitrite.
, The fabric is entered at 20 C. and the temperature raised to 45 C. in 30 minutes, being maintained at this for a further 30 minutes.
After rinsing in dilute sodium carbonate, the material is soaped off in 2 g.p.l. aqueous soap solution for 1 hour at 75-80 C. The fabric is dyed a nigger brown shade. A similar result is obtained if the pH value of the bath is adjusted to 7.0 to 7.5 by addition of dilute acetic acid before addition of the emulsified diethyl phthalate.
Example 6 A treatment bath is made up from thefollowing:
40 1. water 40 g. Lissapol C 20 g. Fast Red RC Base (4-chlor-2-amino-anisole) 20 g. Naphthol AS/BG 6.6 g. caustic soda flakes 200 g. diethyl phthalate The bath is prepared in the manner described in Example 1 except that the pH value is adjusted to 7.0-7.5 by addition of dilute acetic acid before adding the emulsified diethyl phthalate. l
1 kg. of a fabric of cellulose triacetate yarn is then processed in this bath in the manner described inExample l, and then diazotised and further treated as described in that example. A full bright scarlet is obtained.
Example. 7
A treatment bath is prepared from the following:
40 1. Water 40 g. Lissapol C 20 g. Fast Bordeaux GP Base (1-amino-2-nitro-4-methoxy-benzene) 20 g. Naphthol AS/BG 6.6 g. caustic soda flakes 200 g. diethyl phthalate The bath is prepared in the manner described in Example 1 except that the pH value is adjusted to 7.0-7.5 by addition of dilute acetic acid before adding the emulsified diethyl phthalate.
1 kg. of a fabric of cellulose triacetate yarn is then processed in this bath in the manner described in Example 1, and then diazotised and further treated as described in that example. A deep crimson is obtained.
Example 8 q A treatment bath is prepared from the following:
40 1. water 40 g. Lissapol C 10 g. Fast Red GG Base (para nitro aniline) 10 g. Naphthol AS/G 3.3 g. Caustic soda flakes 200 g. diethyl phthalate.
The bath is prepared in the manner described in Example 1 except that the pH value is adjusted to 7.0-7.5 by addition of dilute acetic acid before adding the emulsified diethyl phthalate.
1 kg. of a fabric of cellulose triacetate yarn is then processed in this bath in the manner described in Example 1, and then diazotised and further treated as described in that example. A full golden yellow is obtained.
In any of the above examples the :diethyl phthalate may be replaced by tri-n-propylphosphate with similar results.
Textile fibres of high acetyl cellulose acetate to be coloured in accordance with the invention may be those made by a melt spinning process, especially a process described in United States applications S. Nos. 243,994 filed August 28, 1951, now abandoned, 292,772 filed June 10, 1952, now U.S. Patent No. 2,888,711, 304,441 filed August 14, 1952, now abandoned, 338,834 filed Feb. 2 5, 1953, now US. Patent No. 2,982,597, or 423,743 filed April 16, 1954, now abandoned. In one such process a powdered cellulose ester is urged (e. g. by a rapidly reciprocating tamper) against the side of a heated plate having spinning orifices therein, the powdered ester is fused bythe heat applied to the plate, the fused ester is drawn away from the orifices in the form of filaments, and fresh pow- .dered ester is continuously fed to the plate. The spinning orifices may be circular, or they may be in the form of slits or of two or more closely spaced orintersecting holes, as described in United States application 8. No. 338,834. In another process cellulose triacetate in the form of a coherent rod or a block or tablet of uniform cross-section is pressed axially against a heated plate having spinning orifices therein. Wet and dry spinning methods may also be used to form the cellulose acetate fibres. Thus solutions of high acetyl cellulose acetate in mixtures of methylene or ethylene chloride with methyl or ethyl alcohol or acetic acid, or in acetic acid alone, may be extruded as filaments and set either by means of a coagulating liquid or by an evaporative method. For example solutions of cellulose triacetate in mixtures of methylene or ethylene chloride with acetic acid may be extruded into a coagulating liquid comprising an aqueous alcohol, especially aqueous ethyl alcohol of concentration about 90-95%, as described in United States Patent No. 2,657,973, or solutions in acetic acid may be extruded into aqueous acetic acid which may with advantage contain a fairly high proportion of ammonium or an alkali metal acetate, an alkaline earth metal acetate or magnesium acetate, or of some other salt.
Yet another method by which textile fibres of cellulose acetate of high acetyl value may be obtained is the further acetylation of a textile material of cellulose acetate of lower acetyl value. For instance, yarns or fabrics of acetone-soluble cellulose acetate may be further acetylated with acetic anhydride in the the presence of a diluent such as benzene, and of a basic or acid esterification catalyst such as pyridine, sulphuric acid, perchloric acid or hydrochloric acid, with or without a metal chloride such as zinc chloride or ferric chloride as described in United States Patents Nos. 2,159,011 and 2,159,012.
If desired the fibres of high acetyl cellulose acetate may be those having a high safe ironing such as are described, together with processes for their manufacture, in United States application S. No. 400,798 filed Dec. 28, 1953 now US. Patent No. 2,862,785. Alternatively the materials may, after colouring, be given a treatment such as is described in that application.
The cellulose triacetate yarn of the fabric coloured according to the examples is a product made by dry-spinning a solution of cellulose acetate of about 61% acetyl value in a mixture of methylene chloride and methyl alcohol (ratio about 93:7 by volume).
Having described our invention, what we desire to secure by Letters Patent is:
1. Method of incorporating an enolic azo coupling component in a cellulose triacetate textile material, which comprises allowing the material to take up the coupling component from an aqueous bath having dispersed therein both the coupling component and an assistant consisting essentially of a substantially water-insoluble oxygen containing organic ester which is a solvent for the coupling component and which has a substantive afiinity for the cellulose triacetate.
2. A method according to claim 1, wherein the substantially water-insoluble organic substance is diethyl phthalate present to the extent of from -40% based on the weight of the textile materials.
3. Method of incorporating an enolic azo coupling component in a cellulose triacetate textile material, which comprises allowing the material to take up the coupling component from an aqueous bath at a temperature of 95 to 100 C. and having dispersed therein both the coupling component and from 1040% of diethyl phthalate based on the weight of the textile material.
4. A method of colouring textile material of cellulose triacetate, which comprises allowing the material to take up an enolic azo coupling component and a diazotisable base from an aqueous bath having dispersed therein the coupling component, the base, and an assistant consisting essentially of from 1040% based on the weight of the textile material of a substantially water-insoluble organic substance which is a solvent for the coupling component and which has a substantive afiinity for the cellulose triacetate, and thereafter treating the material to effect diazotisation of the base and coupling of the resulting diazo compound with the coupling component on the material.
5. Method according to claim 4, wherein the enolic coupling component is the 2:5-dimethoxyanilide of 3- hydroxy-diphenylene-oxide-2-carboxylic acid.
6. Method according to claim 4, wherein the enolic coupling component is di-(acetoacetyl)-ortho-tolidine.
7. Method according to claim 4, wherein the aqueous bath has a pH value of from 6-8.
8. Method according to claim 4, wherein the enolic coupling component is an arylamide of 2:3-hydroxynaphthoic acid.
9. Method according to claim 8, wherein the arylamide is the 4'-methoxyanilide.
10. Method according to claim 8, wherein the arylamide is the 2':5-dimethoxyanilide.
11. Method according to claim 8, wherein the arylamide is the 2'-methyl-4-methoxyanilide.
12. A method of colouring cellulose triacetate textile material, which comprises allowing the material to take up an enolic azo coupling component and a diazotisable base from an aqueous bath having dispersed therein the coupling component, the base and from 10-40%, based on the weight of the textile material, of diethyl phthalate, and thereafter treating the material to effect diazotisation of the base and coupling of the resulting diazo compound with the coupling component on the material.
13. Method of incorporating an enolic azo coupling component in a cellulose triacetate textile material, which comprises allowing the material to take up the coupling component from an aqueous bath having dispersed therein both the coupling component and from 10-40%, based on the weight of the textile material, of an assistant consisting essentially of a substantially water-insoluble organic substance which is a solvent for the coupling component and which has a substantive affinity for the cellulose triacetate.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Millin, C.E.: Acetate Silk and Its Dyes, Van Nostrand Co., New York, 1927, pages 251-253.
Fortess, E: Dyeing, Finishing and Heat Treating Arnel Tri-Acetate, Am. Dyestuff Reporter, Aug. 1, 1955, pp. 524537.
Courpleta, Textile Mfgr., February 1955, pages 7172.
Claims (1)
1. METHOD OF INCORPORATING AN ENOLIC AZO COUPLING COMPONENT IN A CELLULOSE TRIACETATE MATERIAL, WHICH COMPRISES ALLOWING THE MATERIAL TO TAKE UP THE COUPLING COMPONENT FROM AN AQUEOUS BATH HAVING DISPERSED THEREIN BOTH THE COUPLING COMPONENT AND AN ASSISTANT CONSISTING ESSENTIALLY OF A SUBSTANTIALLY WATER-INSOLUBLE OXYGEN CONTAINING ORGANIC ESTER WHICH IS A SOLVENT FOR THE COUPLING COMPONENT AND WHICH HAS A SUBSTANTIVE AFFINITY FOR THE CELLULOSE TRIACETATE.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3069219X | 1955-07-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3069219A true US3069219A (en) | 1962-12-18 |
Family
ID=10921027
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US593036A Expired - Lifetime US3069219A (en) | 1955-07-08 | 1956-06-22 | Colouring cellulose triacetate textile materials |
Country Status (1)
Country | Link |
---|---|
US (1) | US3069219A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3164438A (en) * | 1962-03-29 | 1965-01-05 | Hercules Powder Co Ltd | Process for dyeing polypropylene fibers with azoic dyes |
US3206274A (en) * | 1959-07-23 | 1965-09-14 | Celanese Corp | Processing of cellulose triacetate |
US3300245A (en) * | 1966-01-21 | 1967-01-24 | Fenton J Rumble | Picnic table |
US3925013A (en) * | 1973-05-23 | 1975-12-09 | Catawba Chemicals Inc | Eutectic biphenyl-napthalene dye carriers |
US4242094A (en) * | 1976-03-17 | 1980-12-30 | Hoechst Aktiengesellschaft | Dyeing preparations and their use for preparing developing dyes |
US4255153A (en) * | 1979-09-27 | 1981-03-10 | Sandoz, Inc. | Disperse dyeing of triacetate |
WO2008085215A1 (en) * | 2007-01-09 | 2008-07-17 | Health Research, Inc. | Treatment of barrett's esophagus using photodynamic therapy |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1690481A (en) * | 1924-08-14 | 1928-11-06 | Celanese Corp | Dyeing, printing, or stenciling of acetyl cellulose or products made therewith |
US1803008A (en) * | 1931-04-28 | Dyeing | ||
US2048796A (en) * | 1933-06-09 | 1936-07-28 | Celanese Corp | Treatment of textile materials |
US2182964A (en) * | 1936-08-13 | 1939-12-12 | Celanese Corp | Coloration of textile and other materials |
US2188160A (en) * | 1936-10-09 | 1940-01-23 | Colancse Corp Of America | Coloration of artificial textile and other materials |
US2259515A (en) * | 1939-04-22 | 1941-10-21 | Celanese Corp | Dyeing cellulose derivative materials |
US2274751A (en) * | 1942-03-03 | Materials | ||
GB595344A (en) * | 1945-01-17 | 1947-12-02 | United Turkey Red Company Ltd | Improvements in the art of printing textile yarns and fabrics containing cellulose acetate |
-
1956
- 1956-06-22 US US593036A patent/US3069219A/en not_active Expired - Lifetime
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1803008A (en) * | 1931-04-28 | Dyeing | ||
US2274751A (en) * | 1942-03-03 | Materials | ||
US1690481A (en) * | 1924-08-14 | 1928-11-06 | Celanese Corp | Dyeing, printing, or stenciling of acetyl cellulose or products made therewith |
US2048796A (en) * | 1933-06-09 | 1936-07-28 | Celanese Corp | Treatment of textile materials |
US2182964A (en) * | 1936-08-13 | 1939-12-12 | Celanese Corp | Coloration of textile and other materials |
US2188160A (en) * | 1936-10-09 | 1940-01-23 | Colancse Corp Of America | Coloration of artificial textile and other materials |
US2259515A (en) * | 1939-04-22 | 1941-10-21 | Celanese Corp | Dyeing cellulose derivative materials |
GB595344A (en) * | 1945-01-17 | 1947-12-02 | United Turkey Red Company Ltd | Improvements in the art of printing textile yarns and fabrics containing cellulose acetate |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3206274A (en) * | 1959-07-23 | 1965-09-14 | Celanese Corp | Processing of cellulose triacetate |
US3164438A (en) * | 1962-03-29 | 1965-01-05 | Hercules Powder Co Ltd | Process for dyeing polypropylene fibers with azoic dyes |
US3300245A (en) * | 1966-01-21 | 1967-01-24 | Fenton J Rumble | Picnic table |
US3925013A (en) * | 1973-05-23 | 1975-12-09 | Catawba Chemicals Inc | Eutectic biphenyl-napthalene dye carriers |
US4242094A (en) * | 1976-03-17 | 1980-12-30 | Hoechst Aktiengesellschaft | Dyeing preparations and their use for preparing developing dyes |
US4255153A (en) * | 1979-09-27 | 1981-03-10 | Sandoz, Inc. | Disperse dyeing of triacetate |
WO2008085215A1 (en) * | 2007-01-09 | 2008-07-17 | Health Research, Inc. | Treatment of barrett's esophagus using photodynamic therapy |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2274751A (en) | Materials | |
US3069219A (en) | Colouring cellulose triacetate textile materials | |
US3164438A (en) | Process for dyeing polypropylene fibers with azoic dyes | |
US2267842A (en) | Manufacture of artificial materials such as fibers | |
US2923593A (en) | Diethylene glycol diacetate as an assistant in the dyeing of cellulose triacetate | |
US2182964A (en) | Coloration of textile and other materials | |
GB1422995A (en) | Process for the single-bath dyeing of cellulose fibres or mixtures thereof with synthetic fibres with water-insoluble azo dyestuffs produced on the fibre by the exhaustion method | |
US2272810A (en) | Printing cellulosic textile materials | |
US2950949A (en) | Process for dyeing and printing shaped structures of hydrophobic organic high polymers containing ester groups | |
US3391985A (en) | Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions | |
DE1931881A1 (en) | Process for dyeing textile material from mixtures of polyester fibers with cellulose fibers | |
US2347001A (en) | Dyeing cellulose esters | |
GB500960A (en) | Improvements in the treatment of textile materials | |
US2218628A (en) | Coloration of textile and other materials | |
US2439074A (en) | Cellulose acetate fibers having wool dyeing properties and a spinning solution therefor | |
US3787179A (en) | Process for the manufacture of insoluble azo dyestuffs on cellulose fibers | |
US2048796A (en) | Treatment of textile materials | |
US2182963A (en) | Henry dreyfus | |
US2448515A (en) | Dyed cellulose ethers and dyeing of fabrics therewith | |
US1646296A (en) | Fast dyeing on the fiber | |
US3203750A (en) | Process for dyeing shaped articles of polymers of olefinic unsaturated compounds | |
US3679350A (en) | Process for the dyeing of textile materials made from mixtures of polyester and cellulosic fibres | |
US2191887A (en) | Cellulosic structure and process of making the same | |
US2622959A (en) | Dyeing articles made of | |
US1871470A (en) | Dyeing of cellulose derivatives |