EP2699727B1 - Procédé de teinture du polyester - Google Patents
Procédé de teinture du polyester Download PDFInfo
- Publication number
- EP2699727B1 EP2699727B1 EP12707755.0A EP12707755A EP2699727B1 EP 2699727 B1 EP2699727 B1 EP 2699727B1 EP 12707755 A EP12707755 A EP 12707755A EP 2699727 B1 EP2699727 B1 EP 2699727B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- textile material
- hydrogen
- alkyl
- formula
- treated
- 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.)
- Active
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- 229920000728 polyester Polymers 0.000 title claims description 28
- 238000004043 dyeing Methods 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 24
- -1 amino, carboxyl Chemical group 0.000 claims description 30
- 239000000463 material Substances 0.000 claims description 21
- 239000004753 textile Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000000986 disperse dye Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229920000742 Cotton Polymers 0.000 claims description 7
- 229920001732 Lignosulfonate Polymers 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 17
- 239000004744 fabric Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 11
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 9
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LEGWLJGBFZBZSC-UHFFFAOYSA-N n-[2-[(2,6-dicyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(C#N)C=C([N+]([O-])=O)C=C1C#N LEGWLJGBFZBZSC-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- JSRUDOBCTLPTFO-UHFFFAOYSA-N 2-[5-acetamido-n-(2-acetyloxyethyl)-4-[(2-bromo-4,6-dinitrophenyl)diazenyl]-2-methoxyanilino]ethyl acetate Chemical compound C1=C(N(CCOC(C)=O)CCOC(C)=O)C(OC)=CC(N=NC=2C(=CC(=CC=2Br)[N+]([O-])=O)[N+]([O-])=O)=C1NC(C)=O JSRUDOBCTLPTFO-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 description 2
- QDNPLNOHUNPYHZ-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-propoxypiperidine Chemical compound CCCOC1CC(C)(C)N(O)C(C)(C)C1 QDNPLNOHUNPYHZ-UHFFFAOYSA-N 0.000 description 2
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 description 2
- KRNWYBIEWUXCOB-UHFFFAOYSA-N 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidine Chemical compound COC1CC(C)(C)N(O)C(C)(C)C1 KRNWYBIEWUXCOB-UHFFFAOYSA-N 0.000 description 2
- ZDORFLXCSSFUIE-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-chloro-4-nitrophenyl)diazenyl]-3-(propanoylamino)anilino]ethyl acetate Chemical compound CCC(=O)NC1=CC(N(CCOC(C)=O)CCOC(C)=O)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl ZDORFLXCSSFUIE-UHFFFAOYSA-N 0.000 description 2
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- YYTYIUAYFBFKHX-UHFFFAOYSA-N n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical compound CC(=O)NC1CC(C)(C)N(O)C(C)(C)C1 YYTYIUAYFBFKHX-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- DHQPJBANLLHLPK-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl) acetate;acetate Chemical compound CC([O-])=O.CC(=O)OC1CC(C)(C)[NH+](O)C(C)(C)C1 DHQPJBANLLHLPK-UHFFFAOYSA-N 0.000 description 1
- FXFIDVQMNRVEGQ-UHFFFAOYSA-N (7e)-3-(diethylamino)-7-imino-7h-chromeno[3',2':3,4]pyrido[1,2-a]benzimidazole-6-carbonitrile Chemical compound C1=CC=C2N(C(=N)C(C#N)=C3C4=CC5=CC=C(C=C5O3)N(CC)CC)C4=NC2=C1 FXFIDVQMNRVEGQ-UHFFFAOYSA-N 0.000 description 1
- IFKZOCCBNRTDNL-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)peroxybutan-1-ol;acetate Chemical compound CC([O-])=O.CCCC(O)OOC1CC(C)(C)[NH+](O)C(C)(C)C1 IFKZOCCBNRTDNL-UHFFFAOYSA-N 0.000 description 1
- DOIAXYYFHLZFJT-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethyl-4-propoxypiperidin-1-ium;acetate Chemical compound CC([O-])=O.CCCOC1CC(C)(C)[NH+](O)C(C)(C)C1 DOIAXYYFHLZFJT-UHFFFAOYSA-N 0.000 description 1
- QCJDXHSSMDQRBO-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-ol;chloride Chemical compound [Cl-].CC1(C)CC(O)CC(C)(C)[NH+]1O QCJDXHSSMDQRBO-UHFFFAOYSA-N 0.000 description 1
- OMLXPSWZYGQPCR-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-one;acetate Chemical compound CC([O-])=O.CC1(C)CC(=O)CC(C)(C)[NH+]1O OMLXPSWZYGQPCR-UHFFFAOYSA-N 0.000 description 1
- PHVZJHXYLWVJIP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidine;piperidin-4-ol Chemical compound OC1CCNCC1.CC1(C)CCCC(C)(C)N1O PHVZJHXYLWVJIP-UHFFFAOYSA-N 0.000 description 1
- NIPVMEKAVWIWRO-UHFFFAOYSA-N 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidin-1-ium;acetate Chemical compound CC([O-])=O.COC1CC(C)(C)[NH+](O)C(C)(C)C1 NIPVMEKAVWIWRO-UHFFFAOYSA-N 0.000 description 1
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 1
- ZRLYFONGBAKSBB-OFWBYEQRSA-N 2-[(2z)-2-[[4-(dihexylamino)-2-methylphenyl]methylidene]-1,1-dioxo-1-benzothiophen-3-ylidene]propanedinitrile Chemical compound CC1=CC(N(CCCCCC)CCCCCC)=CC=C1\C=C\1S(=O)(=O)C2=CC=CC=C2C/1=C(C#N)C#N ZRLYFONGBAKSBB-OFWBYEQRSA-N 0.000 description 1
- QEORVDCGZONWCJ-UHFFFAOYSA-N 2-[[4-[2-cyanoethyl(ethyl)amino]phenyl]diazenyl]-5-nitrobenzonitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N QEORVDCGZONWCJ-UHFFFAOYSA-N 0.000 description 1
- GRMDKKJYMUDEJO-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-cyano-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCOC(C)=O)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N GRMDKKJYMUDEJO-UHFFFAOYSA-N 0.000 description 1
- ROPYWXVRNREIQD-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ROPYWXVRNREIQD-UHFFFAOYSA-N 0.000 description 1
- QLRDACXDRLGLOC-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 QLRDACXDRLGLOC-UHFFFAOYSA-N 0.000 description 1
- VZOFQIJZHYEQSJ-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylate;(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl) acetate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.CC(=O)OC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)OC1CC(C)(C)[NH+](O)C(C)(C)C1.CC(=O)OC1CC(C)(C)[NH+](O)C(C)(C)C1 VZOFQIJZHYEQSJ-UHFFFAOYSA-N 0.000 description 1
- TXXNVPVRPSACBM-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.CC1(C)CC(O)CC(C)(C)[NH+]1O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O TXXNVPVRPSACBM-UHFFFAOYSA-N 0.000 description 1
- UTTFXJZCRVZYQF-UHFFFAOYSA-N 3-(diethylamino)-7-oxo-7h-(1)benzopyrano(3',2':3,4)pyrido(1,2-a)benzimidazole-6-carbonitrile Chemical compound C1=CC=C2N(C(=O)C(C#N)=C3C4=CC5=CC=C(C=C5O3)N(CC)CC)C4=NC2=C1 UTTFXJZCRVZYQF-UHFFFAOYSA-N 0.000 description 1
- MWMJPPMTXZJLIK-UHFFFAOYSA-N 3-[4-[(2,6-dibromo-4-nitrophenyl)diazenyl]-n-ethylanilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1Br MWMJPPMTXZJLIK-UHFFFAOYSA-N 0.000 description 1
- ZXXVVTBKBDDTSE-UHFFFAOYSA-N 3-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-(2-cyanoethyl)anilino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=C(N(CCC#N)CCC#N)C=C1 ZXXVVTBKBDDTSE-UHFFFAOYSA-N 0.000 description 1
- NPBDWXMKLFBNIW-UHFFFAOYSA-N 3-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-ethylanilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl NPBDWXMKLFBNIW-UHFFFAOYSA-N 0.000 description 1
- ZSPPPAFDNHYXNW-UHFFFAOYSA-N 3-[n-ethyl-4-[(4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 ZSPPPAFDNHYXNW-UHFFFAOYSA-N 0.000 description 1
- WBCXRDHKXHADQF-UHFFFAOYSA-N 4,11-diamino-2-(3-methoxypropyl)naphtho[2,3-f]isoindole-1,3,5,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(N(CCCOC)C1=O)=O)C1=C2N WBCXRDHKXHADQF-UHFFFAOYSA-N 0.000 description 1
- AIARLPIXVMHZLJ-UHFFFAOYSA-N 4,8-diamino-2-bromo-1,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=C(Br)C(O)=C2C(=O)C2=C1C(O)=CC=C2N AIARLPIXVMHZLJ-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- LUTRAMFAYXFIQK-UHFFFAOYSA-N acetic acid;1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC([O-])=O.CC1(C)CC(O)CC(C)(C)[NH+]1O LUTRAMFAYXFIQK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- GQSGZTBDVNUIQS-DGCLKSJQSA-N ciclonicate Chemical compound C1C(C)(C)C[C@H](C)C[C@H]1OC(=O)C1=CC=CN=C1 GQSGZTBDVNUIQS-DGCLKSJQSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- REZIEVJVJYHZKK-UHFFFAOYSA-N hydrogen sulfate;1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-ol Chemical compound OS([O-])(=O)=O.CC1(C)CC(O)CC(C)(C)[NH+]1O REZIEVJVJYHZKK-UHFFFAOYSA-N 0.000 description 1
- XQEZPIIANZJBMP-UHFFFAOYSA-N hydrogen sulfate;n-(1-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-yl)acetamide Chemical compound OS([O-])(=O)=O.CC(=O)NC1CC(C)(C)[NH+](O)C(C)(C)C1 XQEZPIIANZJBMP-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- WFFKSTRPZWRBEW-UHFFFAOYSA-N n-[2-[(2-bromo-4,6-dinitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O WFFKSTRPZWRBEW-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 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
- 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
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
-
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- 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
- D06P3/52—Polyesters
Definitions
- the present invention relates to a method of dyeing polyester-containing textile material.
- Reduction sensitivity of azo disperse dyes is a problem in the polyester dyeing process.
- the extent of dye destruction in the dye liquor depends on the chemical structure of the dye, the processing conditions and the type of dyeing auxiliaries. This reduction sensitivity seriously affects the reproducibility of the shade, especially in combination dyeings.
- Critical dyeing conditions are fully flooded bulk dyeing machines, wherein the air and the oxygen are completely removed. Lignin sulfonate dispersing agents are widely used because of their low price and their reliability, especially at high dyeing temperatures (130 - 135°C), but due to their reduction power these dispersants tend to destroy reduction-sensitive disperse dyes in the dye liquor.
- any disperse dye known for dyeing polyester can be used in the process according to the invention.
- component (a) is a compound of formula or
- the disperse dyes of formulae (2), (3) and (4) are known or can be prepared according to known methods.
- disperse dyes are preferFred: C.I. Disperse Yellow 114, C.I. Disperse Yellow 211, C.I. Disperse Yellow 54, C.I. Disperse Orange 25, C.I. Disperse Orange 30, C.I. Disperse Orange 31, C.I. Disperse Orange 44, C.I. Disperse Orange 61, C.I. Disperse Red 50, C.I. Disperse Red 73, C.I. Disperse Red 82, C.I. Disperse Red 167, Disperse Red 167:1, C.I. Disperse Red 324, C.I. Disperse Red 356, C.I. Disperse Red 376, C.I. Disperse Red 382, C.I.
- component (a) are the compounds of formula and
- the compounds of formula (1) likewise are known and are described, for example, in WO 01/85857 .
- the component (b) to be used in the method according to the invention also includes the ammonium salts obtainable by reaction of the compound of formula (1) with acids.
- Suitable compounds of the formula (1a) are, for example, bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 1-hydroxy-2,2,6,6-tetramethyl-4-acetoxypiperidinium citrate, 1-oxyl-2,2,6,6-tetramethyl-4-acetamidopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-acetamidopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-acetamidopiperidinium bisulfate, 1-oxyl-2,2,6,6-tetramethyl-4-oxopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine, 1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidinium acetate, 1-oxyl-2,2,6,6-tetramethyl-4-methoxypiperidine,
- the textile material is treated with a liquor containing as component (b) 1-oxyl-2,2,6,6-tetramethyl-4-hydroxypiperidine of the formula
- the dyes according to component (a) can be applied individually or in mixtures.
- mixtures of two or three dyes may be used.
- Mixtures of four or more dyes can also be used, especially in the production of combination shades.
- the amounts in which the individual dyes are used in the dye liquors can vary within wide limits depending on the desired depth of shade. In general, amounts of from 0.01 to 35 % by weight, especially from 0.1 to 15 % by weight, based on the fibre material to be dyed have proved to be advantageous.
- the liquor ratio can be selected from within a wide range, for example within a range of from 1:2 to 1:50, preferably from 1:3 to 1:15.
- the liquor can comprise, in addition to components (a) and (b) as defined above, further customary additives, such as dispersing, levelling and wetting agents, penetration accelerants, pH-regulators and antifoams.
- further customary additives such as dispersing, levelling and wetting agents, penetration accelerants, pH-regulators and antifoams.
- Suitable dispersing agents can be nonionic or anionic.
- Nonionic dispersing agents are, for example, reaction products of alkylene oxides, like ethylene oxide or propylene oxide, with fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
- Anionic dispersing agents are, for example, lignin sulfonates and salts thereof, alkyl- or alkylaryl-sulfonates, alkylaryl polyglycol ether sulfates, alkali metal salts of the condensation products of naphthalenesulfonic acids and formaldehyde, polyvinyl sulfonates and ethoxylated novolaks.
- the textile material is treated with a liquor additionally containing a lignin sulfonate as dispersing agent.
- the textile material can be used in any form, e.g. in the form of fibres, yarn, woven fabric, knitted fabric or non-woven.
- Polyester-containing textile material in terms of the invention includes pure polyester as well as blends containing polyester and further synthetic, semi-synthetic or natural textile material, like polyester/cotton, polyester/wool or polyester/elastan blends.
- the textile material is polyester or a polyester/cotton blend.
- polyester fibre materials are dyed from an aqueous dispersion by the exhaust process in the presence of customary anionic or nonionic dispersants and in the presence or absence of customary swelling agents (carriers) at pH 3.5 - 5.5, in particular at pH 4.0 - 5.0, in the temperature range from 80 to 150 °C, preferably from 90 to 140 °C.
- Special apparatus is not required.
- customary dyeing apparatus e.g. open baths, winch becks, jigs, or paddle, jet or circulation apparatus, may be used.
- an aftertreatment can be carried out at a pH value of e.g. from 7 to 12, especially from 7 to 9, and a temperature of e.g. from 30 to 100 °C, especially from 50 to 80 °C, to remove any unfixed dye.
- unfixed dye can advantageously be removed reductively, by adding to the alkaline aftertreatment bath a reducing agent, for example a hydrosulfite, e.g. sodium hydrosulfite.
- Dye that has been fixed in the fibre material is not attacked by the treatment.
- the amount of reducing agent added is e.g. from 0.1 to 8.0 % by weight, especially from 0.5 to 5.0 % by weight, based on the weight of the aftertreatment bath.
- 10 g knitted 100% polyester fabric is dyed in an autoclave by preparing a dye liquor of 100 ml total volume containing 45 mg of a commercial formulation of C.I. Disperse Blue 165:1, 50 mg of a compound of formula (101), 200 mg of a commercial dispersing agent (REAX 85A, lignin sulfonate, supplied by BASF), 50 mg of a commercial wetting and defoaming agent (ALBAFLOW ® UNI, supplied by Huntsman), 100 mg ammonium sulfate and about 0.1 ml of acetic acid 80% to get pH of 4.5.
- a commercial dispersing agent RX 85A, lignin sulfonate, supplied by BASF
- ABAFLOW ® UNI commercial wetting and defoaming agent
- the fabric is put into the dye liquor and just before closing the autoclave it is thoroughly washed with nitrogen to simulate a fully flooded bulk dyeing machine, where all the air and the oxygen with it is removed completely.
- the liquor is heated up with 2 °C per minute to 135 °C and is kept at 135 °C for 60 minutes.
- After a warm and cold rinse the dyeing is treated in a reductive clearing: 20 min/70 °C in a liquor containing 5 ml/l caustic soda 36°Be, 2 g/l sodium hydrosulfite conc. and 1 g/l of a commercial nonionic washing agent (ERIOPON ® OL, supplied by Huntsman).
- the dyeing is rinsed, neutralized and dried.
- the depth of shade is determined by reflectance measurement and expressed in percentage in relation to the depth of shade which is obtained by a benchmark process carried out with same fabric, dye and auxiliaries but using UNIVADINE ® DP (dispersing agent, supplied by Huntsman) instead of the compound of formula (101), which is set as 100%.
- Example 1 and Comparative Example 2 are repeated with other dyes. The resulting depth of shade values are summarized in Table 1.
- Table 1 Series with 100% polyester fabric Comparative Example 2
- Example 1 45 mg C.I. Disperse Blue 165:1 30% 71% 51 mg C.I. Disperse Blue 79.1 73% 98% 70 mg C.I. Disperse Blue 378 76% 93%
- Inventive Example 1 and Comparative Example 2 is made with a fabric blend of 65% grey cotton and 35% polyester instead of the 100% polyester fabric and without the 200 mg of commercial lignin sulfonate dispersing agent (REAX 85A) in the comparative example 1 and in the inventive example 2.
- REAX 85A commercial lignin sulfonate dispersing agent
- Table 2 Series with fabric blend of 65% cotton / 35% polyester without REAX 85A Comparative Example 2 Inventive Example 1 45 mg C.I. Disperse Blue 165:1 45% 62% 51 mg C.I. Disperse Blue 79:1 68% 87% 70 mg C.I. Disperse Blue 378 73% 85%
- Comparative Example 2 and Example 1 is made with a fabric blend of 65% cotton and 35% polyester instead of the 100% polyester fabric and without the 200 mg of commercial lignin sulfonate dispersing agent (REAX 85A) and without the washing with nitrogen.
- the resulting depth of shade values are summarized in Table 3.
- Table 3 Series with fabric blend of 65% cotton / 35% polyester without REAX 85A and without nitrogen washing Comparative Example 2
- Inventive Example 1 45 mg Disperse Blue 165:1 81% 92% 51 mg Disperse Blue 79:1 85% 92% 70 mg Disperse Blue 378 90% 92%
- 5 g knitted 100% polyester fabric is dyed in an autoclave with a dye liquor of 50 ml total volume containing 75 mg of a commercial formulation of C.I. Disperse Red 277 (Solvent Red 197), 20 mg of a compound of formula (101), 100 mg of a commercial wetting and defoaming agent (ALBAFLOW ® UNI, supplied by Huntsman), 50 mg ammonium sulfate and about 0.05 ml of acetic acid 80% to get pH of 4.5.
- the liquor is heated up with 2 °C per minute to 135 °C and is kept at 135 °C for 60 minutes.
- the dyeing After a warm and cold rinse the dyeing is subjected to a reductive aftertreatment: 20 min/70 °C in a liquor containing 5 ml/l caustic soda 36°Bé, 2 g/l sodium hydrosulfite conc. and 1 g/l of a commercial nonionic washing agent (ERIOPON ® OL, supplied by Huntsman). The dyeing is rinsed, neutralized and dried.
- ERIOPON ® OL commercial nonionic washing agent
- the dyeing of the Inventive Example 3 provides a significantly more brilliant shade and a significantly stronger fluorescence compared to the dyeing of the Comparative Example 4.
- Example 3 and 4 are repeated by replacing 75 mg Disperse Red 277 with 75 mg Disperse Red 362 (Solvent Red 196) providing the same positive effect on shade and fluorescence in the case of Example 5 (use of the compound of formula (101)) compared to Example 6.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Claims (9)
- Procédé de teinture d'une matière textile à teneur en polyester, caractérisé par le fait que la matière textile est traitée par une liqueur contenant :(a) au moins un colorant dispersé et(b) au moins un composé de la formule :- G1 et G2, indépendamment l'un de l'autre, représentent alkyle en C1-C4 ou représentent ensemble pentaméthylène,- Z1 et Z2 représentent méthyle, ou Z1 et Z2 forment ensemble un élément pontant qui est non substitué ou substitué par un radical ester, éther, hydroxyle, oxo, cyanhydrine, amido, amino, carboxyle ou uréthane, et- E représente oxyle ou hydroxyle.
- Procédé selon la revendication 1, dans lequel la matière textile est traitée par une liqueur contenant comme composant (a) un composé de formule :- R1 représente alkyle en C1-C4,- R2 représente hydrogène, bromo, chloro, cyano ou nitro,- R3 représente bromo, chloro, cyano ou nitro,- R4 représente hydrogène, méthyle ou méthoxy,- R5 et R6, indépendamment l'un de l'autre, représentent éthyle, benzyle, 2-cyanoéthyle, 2-hydroxyéthyle, 2-méthoxyéthyle, 2-éthoxyéthyle, 2-(2-méthoxyéthoxy)-éthyle, 2-(2-éthoxyéthoxy)-éthyle, 2-acétyloxyéthyle, méthoxycarbonylméthyle, éthoxycarbonylméthyle, 1-méthoxycarbonyléthyle ou 1-éthoxycarbonyléthyle,- R7 représente hydrogène, bromo, chloro, cyano ou nitro,- R8 représente bromo, chloro, cyano ou nitro,- R9 représente méthyle ou éthyle et- R10 représente hydrogène, méthyle, méthoxy, acétylamino ou propionylamino.
- Procédé selon l'une quelconque des revendications précédentes, dans lequel la matière textile est traitée par une liqueur contenant comme composant (b) un composé de formule :- E représente oxyle ou hydroxyle,- R11 représente hydrogène ou méthyle et- n = 1 ou 2,
si n = 1,• Y représente hydrogène, alkyle en C1-C18, alcényle en C2-C10, propargyle, glycidyle ou alkyle en C2-C50 qui est non substitué ou substitué par 1-10 groupes hydroxyle et qui peut être interrompu par 1-20 atomes d'oxygène, ou• Y représente alkyle en C1-C4 substitué par -COOR12, dans lequel R12 représente hydrogène, alkyle en C1-C4 ou phényle,si n = 2,• Y représente alkylène en C1-C12, alcénylène en C4-C12, xylylène ou alkylène en C1-C50, qui est non substitué ou substitué par 1-10 groupes hydroxyle et qui peut être interrompu par 1-20 atomes d'oxygène. - Procédé selon l'une quelconque des revendications précédentes, dans lequel la matière textile est traitée par une liqueur contenant de plus un lignine sulfonate.
- Procédé selon l'une quelconque des revendications précédentes, dans lequel la matière textile est le polyester ou un mélange polyester/coton.
- Procédé selon l'une quelconque des revendications précédentes, dans lequel le traitement par la liqueur de teinture est suivi par un post-traitement réducteur.
- Procédé selon la revendication 7 dans lequel l'hydrosulfite de sodium est utilisé dans l'étape de post-traitement réducteur.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP12707755.0A EP2699727B1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP11163130 | 2011-04-20 | ||
EP12707755.0A EP2699727B1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
PCT/EP2012/053882 WO2012143167A1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
Publications (2)
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EP2699727A1 EP2699727A1 (fr) | 2014-02-26 |
EP2699727B1 true EP2699727B1 (fr) | 2014-11-19 |
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EP12707755.0A Active EP2699727B1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
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US (1) | US20140041134A1 (fr) |
EP (1) | EP2699727B1 (fr) |
JP (1) | JP5913566B2 (fr) |
KR (1) | KR101902752B1 (fr) |
CN (1) | CN103502528B (fr) |
BR (1) | BR112013026857B8 (fr) |
ES (1) | ES2528911T3 (fr) |
TW (1) | TWI540236B (fr) |
WO (1) | WO2012143167A1 (fr) |
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JP2020525580A (ja) * | 2017-06-28 | 2020-08-27 | ハンツマン アドバンスト マテリアルズ (スイッツァランド) ゲーエムベーハーHuntsman Advanced Materials (Switzerland) Gmbh | 分散アゾ染料 |
CN114437564B (zh) * | 2022-02-28 | 2024-04-02 | 浙江万丰化工股份有限公司 | 一种高牢度分散染料组合物及其应用 |
CN116082857A (zh) * | 2022-12-27 | 2023-05-09 | 浙江闰土股份有限公司 | 蓝色分散染料组合物、蓝色分散染料及其制备方法和用途 |
CN115850997B (zh) * | 2022-12-27 | 2024-04-12 | 浙江闰土股份有限公司 | 蓝色分散染料组合物、蓝色分散染料及其制备方法和用途 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE788960A (fr) * | 1971-09-18 | 1973-03-19 | Hoechst Ag | Procede de realisation de teintures et impressions solides a lalumiere sur des fibres synthetiques |
JPS5423783A (en) * | 1977-07-15 | 1979-02-22 | Sanyo Chemical Ind Ltd | High temperature dyeing of polyester fiber |
JPS5936035B2 (ja) * | 1980-05-13 | 1984-08-31 | 住友化学工業株式会社 | 疎水性繊維材料の染色方法 |
JPS60252785A (ja) * | 1984-05-29 | 1985-12-13 | 共同薬品株式会社 | 光堅牢度の優れたポリエステル系染色糸又は染色織布 |
EP0409771A3 (en) * | 1989-06-27 | 1991-06-12 | Ciba-Geigy Ag | Process of photochemical and thermal stabilization of polyamide fibres, dyeable by acid and basic dyes, and of their mixtures amongst themselves and with other fibres |
WO2001085857A1 (fr) | 2000-05-11 | 2001-11-15 | Ciba Specialty Chemicals Holding Inc. | Procede de teinture du bois a l'aide de teintures aqueuses pour bois |
PL362433A1 (en) * | 2001-01-16 | 2004-11-02 | Ciba Specialty Chemicals Holding Inc. | Ink-jet ink and recording material |
WO2003103622A1 (fr) * | 2002-05-02 | 2003-12-18 | Ciba Specialty Chemicals Holding Inc. | Produits pour soins corporels stabilises, produits menagers, textiles et tissus |
JP5384791B2 (ja) * | 2003-11-03 | 2014-01-08 | チバ ホールディング インコーポレーテッド | 安定化されたボディケア製品、家庭用製品、生地及び繊維 |
KR20080094954A (ko) * | 2006-02-17 | 2008-10-27 | 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 | 폴리에스테르의 염색 방법 |
-
2012
- 2012-03-07 ES ES12707755.0T patent/ES2528911T3/es active Active
- 2012-03-07 US US14/112,245 patent/US20140041134A1/en not_active Abandoned
- 2012-03-07 BR BR112013026857A patent/BR112013026857B8/pt active IP Right Grant
- 2012-03-07 KR KR1020137030664A patent/KR101902752B1/ko active IP Right Grant
- 2012-03-07 EP EP12707755.0A patent/EP2699727B1/fr active Active
- 2012-03-07 WO PCT/EP2012/053882 patent/WO2012143167A1/fr active Application Filing
- 2012-03-07 JP JP2014505550A patent/JP5913566B2/ja active Active
- 2012-03-07 CN CN201280019388.9A patent/CN103502528B/zh active Active
- 2012-04-18 TW TW101113744A patent/TWI540236B/zh active
Also Published As
Publication number | Publication date |
---|---|
US20140041134A1 (en) | 2014-02-13 |
TWI540236B (zh) | 2016-07-01 |
JP5913566B2 (ja) | 2016-04-27 |
WO2012143167A1 (fr) | 2012-10-26 |
CN103502528B (zh) | 2017-10-20 |
BR112013026857B8 (pt) | 2023-05-16 |
JP2014516390A (ja) | 2014-07-10 |
BR112013026857B1 (pt) | 2020-09-29 |
CN103502528A (zh) | 2014-01-08 |
ES2528911T3 (es) | 2015-02-13 |
TW201303112A (zh) | 2013-01-16 |
EP2699727A1 (fr) | 2014-02-26 |
KR101902752B1 (ko) | 2018-10-02 |
KR20140025476A (ko) | 2014-03-04 |
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