EP2699727A1 - Procédé de teinture du polyester - Google Patents
Procédé de teinture du polyesterInfo
- Publication number
- EP2699727A1 EP2699727A1 EP12707755.0A EP12707755A EP2699727A1 EP 2699727 A1 EP2699727 A1 EP 2699727A1 EP 12707755 A EP12707755 A EP 12707755A EP 2699727 A1 EP2699727 A1 EP 2699727A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- textile material
- hydrogen
- liquor
- alkyl
- 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.)
- Granted
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 28
- 238000004043 dyeing Methods 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 26
- -1 amino, carboxyl Chemical group 0.000 claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 23
- 239000004753 textile Substances 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 239000000986 disperse dye Substances 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003368 amide group Chemical group 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 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 abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229920001732 Lignosulfonate Polymers 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 6
- 229920000742 Cotton Polymers 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005466 alkylenyl 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
- 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
- 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
- 241000518994 Conta Species 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 17
- 239000002270 dispersing agent Substances 0.000 description 11
- 239000004744 fabric Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 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 8
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000005406 washing Methods 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 229910052757 nitrogen Inorganic materials 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
- 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 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
- Gi and G 2 independently of one another, are C C 4 alkyl or together are pentamethylene, Zi and Z 2 are methyl, ⁇ ⁇ ⁇ and Z 2 together form a bridging member which is
- E is oxyl or hydroxyl.
- any disperse dye known for dyeing polyester can be used in the process according to the invention.
- R 2 is hydrogen, bromo, chloro, cyano or nitro
- R 4 is hydrogen, methyl or methoxy
- R 5 and R 6 independently of one another, are ethyl, benzyl, 2-cyanoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-(2-methoxyethoxy)-ethyl, 2-(2-ethoxyethoxy)-ethyl, 2-acetyloxyethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl or 1-ethoxycarbonylethyl,
- R 7 is hydrogen, bromo, chloro, cyano or nitro
- R 8 is bromo, chloro, cyano or nitro
- Rio is hydrogen, methyl, methoxy, acetylamino or propionylamino.
- the disperse dyes of formulae (2), (3) and (4) are known or can be prepared according to known methods.
- the following 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. Disperse Red 383, C.I. Disperse Violet 93:1 , C.I. Disperse Violet 107, C.I. Disperse Blue 56, C.I. Disperse Blue 60, C.I.
- 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.
- Rii is hydrogen or methyl
- n 1 or 2
- Y is hydrogen, CrCi 8 alkyl, C 2 -Ci 0 alkenyl, propargyl, glycidyl or C 2 -C 50 alkyl which is unsubstituted or substituted by 1 - 10 hydroxyl groups and which may be interrupted by 1 - 20 oxygen atoms, or
- Y is CrCi 2 alkylene, C 4 -Ci 2 alkenylene, xylylene or CrC 50 alkylene, which is
- Suitable compounds of the formula (1a) are, for example,
- 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
- 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 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.
- 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 cone, 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%.
- UNIVADINE ® DP disersing agent, supplied by Huntsman
- Example 1 and Comparative Example 2 are repeated with other dyes.
- the resulting depth of shade values are summarized in Table 1.
- 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.
- 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.
- 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)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
---|---|---|---|
EP11163130 | 2011-04-20 | ||
PCT/EP2012/053882 WO2012143167A1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
EP12707755.0A EP2699727B1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2699727A1 true EP2699727A1 (fr) | 2014-02-26 |
EP2699727B1 EP2699727B1 (fr) | 2014-11-19 |
Family
ID=44544002
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP12707755.0A Active EP2699727B1 (fr) | 2011-04-20 | 2012-03-07 | Procédé de teinture du polyester |
Country Status (9)
Country | Link |
---|---|
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) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3645632B1 (fr) | 2017-06-28 | 2023-03-29 | Huntsman Textile Effects (Switzerland) GmbH | Colorants azo dispersés |
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 |
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 |
AU7398501A (en) | 2000-05-11 | 2001-11-20 | Ciba Sc Holding Ag | Process for the staining of wood with aqueous wood stains |
CA2431999C (fr) * | 2001-01-16 | 2010-04-06 | Ciba Specialty Chemicals Holding Inc. | Encre et support d'impression pour impression par jet d'encre |
MXPA04010833A (es) * | 2002-05-02 | 2005-02-14 | Ciba Sc Holding Ag | Productos para el cuidado del cuerpo, productos para el hogar, textiles y telas estabilizados. |
KR101158266B1 (ko) * | 2003-11-03 | 2012-06-19 | 시바 홀딩 인코포레이티드 | 안정화된 바디 케어 제품, 가정용품, 직물원료 및 직물 |
KR20080094954A (ko) * | 2006-02-17 | 2008-10-27 | 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 | 폴리에스테르의 염색 방법 |
-
2012
- 2012-03-07 CN CN201280019388.9A patent/CN103502528B/zh active Active
- 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 KR KR1020137030664A patent/KR101902752B1/ko active IP Right Grant
- 2012-03-07 US US14/112,245 patent/US20140041134A1/en not_active Abandoned
- 2012-03-07 ES ES12707755.0T patent/ES2528911T3/es active Active
- 2012-03-07 BR BR112013026857A patent/BR112013026857B8/pt active IP Right Grant
- 2012-03-07 JP JP2014505550A patent/JP5913566B2/ja active Active
- 2012-04-18 TW TW101113744A patent/TWI540236B/zh active
Non-Patent Citations (1)
Title |
---|
See references of WO2012143167A1 * |
Also Published As
Publication number | Publication date |
---|---|
TW201303112A (zh) | 2013-01-16 |
CN103502528B (zh) | 2017-10-20 |
KR20140025476A (ko) | 2014-03-04 |
EP2699727B1 (fr) | 2014-11-19 |
JP5913566B2 (ja) | 2016-04-27 |
CN103502528A (zh) | 2014-01-08 |
BR112013026857B1 (pt) | 2020-09-29 |
ES2528911T3 (es) | 2015-02-13 |
KR101902752B1 (ko) | 2018-10-02 |
WO2012143167A1 (fr) | 2012-10-26 |
JP2014516390A (ja) | 2014-07-10 |
TWI540236B (zh) | 2016-07-01 |
BR112013026857B8 (pt) | 2023-05-16 |
US20140041134A1 (en) | 2014-02-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI633158B (zh) | 分散染料混合物,彼之製備及用途 | |
KR101346852B1 (ko) | 고 습윤견뢰도의 흑색 및 네이비블루 분산염료 조성물 | |
WO2007093505A1 (fr) | Procede de coloration de polyester | |
TWI460235B (zh) | 分散染料混合物、它們的製備及用途 | |
ES2398796T3 (es) | Tintes dispersos de AZOPIRIDONA, su preparación y uso | |
EP2699727B1 (fr) | Procédé de teinture du polyester | |
DE69908619T2 (de) | Wässriges präparat eines uv-aktiven mittels und seine herstellung sowie seine verwendung | |
US20070000076A1 (en) | Process for printing or dyeing cellulose/polyester mixed fibres | |
CN112805274B (zh) | 吡啶和嘧啶取代的三嗪紫外线吸收剂 | |
KR20090016558A (ko) | 분산 염료, 제조 및 용도 | |
CA2609780A1 (fr) | Colorants plastosolubles bleus grand teint a temperatures elevees | |
US20240102236A1 (en) | New Pyridine And Pyrimidine Substituted Triazine UV Absorbers | |
EP0864687A2 (fr) | Procédé pour améliorer les solidités photochimiques des matériaux teints et imprimés à base de fibres de polyester | |
JPH08246360A (ja) | ポリエステル及びポリエステル含有繊維材料を染色する方法 | |
KR20000063270A (ko) | 모노아조 염료 조성물 및 이를 이용한 폴리에스테르계직물의 염색 또는 날염방법 | |
KR20000041350A (ko) | 고견뢰도의 분산염료조성물 | |
US20080189882A1 (en) | Hot-Light Resistant Blue Dispersion Dyes | |
CN106752075A (zh) | 一种鲜艳红色分散染料组合物 | |
JPH02232266A (ja) | モノアゾ染料、その製造方法及びその使用方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20130917 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
DAX | Request for extension of the european patent (deleted) | ||
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
INTG | Intention to grant announced |
Effective date: 20140813 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: REF Ref document number: 697124 Country of ref document: AT Kind code of ref document: T Effective date: 20141215 |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602012003889 Country of ref document: DE Effective date: 20141231 |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2528911 Country of ref document: ES Kind code of ref document: T3 Effective date: 20150213 |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: VDEP Effective date: 20141119 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 697124 Country of ref document: AT Kind code of ref document: T Effective date: 20141119 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG4D |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150219 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150319 Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150319 Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150220 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: CY Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602012003889 Country of ref document: DE |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed |
Effective date: 20150820 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: LU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20150307 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20150331 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20150331 Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20150307 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 5 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 6 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 Ref country code: HU Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT; INVALID AB INITIO Effective date: 20120307 Ref country code: SM Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: PLFP Year of fee payment: 7 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20141119 |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: 732E Free format text: REGISTERED BETWEEN 20230105 AND 20230111 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R081 Ref document number: 602012003889 Country of ref document: DE Owner name: HUNTSMAN TEXTILE EFFECTS (SWITZERLAND) GMBH, CH Free format text: FORMER OWNER: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH, BASEL, CH Ref country code: DE Ref legal event code: R081 Ref document number: 602012003889 Country of ref document: DE Owner name: ARCHROMA (SWITZERLAND) GMBH, CH Free format text: FORMER OWNER: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH, BASEL, CH |
|
REG | Reference to a national code |
Ref country code: ES Ref legal event code: PC2A Owner name: HUNTSMAN TEXTILE EFFECTS (SWITZERLAND) GMBH Effective date: 20230619 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R081 Ref document number: 602012003889 Country of ref document: DE Owner name: ARCHROMA (SWITZERLAND) GMBH, CH Free format text: FORMER OWNER: HUNTSMAN TEXTILE EFFECTS (SWITZERLAND) GMBH, BASEL, CH |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20240328 Year of fee payment: 13 Ref country code: GB Payment date: 20240319 Year of fee payment: 13 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: TR Payment date: 20240219 Year of fee payment: 13 Ref country code: IT Payment date: 20240321 Year of fee payment: 13 Ref country code: FR Payment date: 20240326 Year of fee payment: 13 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 20240412 Year of fee payment: 13 |