EP0957197B1 - Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien - Google Patents
Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien Download PDFInfo
- Publication number
- EP0957197B1 EP0957197B1 EP99810385A EP99810385A EP0957197B1 EP 0957197 B1 EP0957197 B1 EP 0957197B1 EP 99810385 A EP99810385 A EP 99810385A EP 99810385 A EP99810385 A EP 99810385A EP 0957197 B1 EP0957197 B1 EP 0957197B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- meth
- parts
- acid
- homopolymer
- copolymer
- 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
- 239000004952 Polyamide Substances 0.000 title claims description 31
- 229920002647 polyamide Polymers 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 28
- 239000002657 fibrous material Substances 0.000 title description 23
- 239000000975 dye Substances 0.000 claims description 28
- 229920001577 copolymer Polymers 0.000 claims description 23
- 238000004043 dyeing Methods 0.000 claims description 23
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 11
- 229920001519 homopolymer Polymers 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000001000 anthraquinone dye Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 229920000642 polymer Polymers 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- -1 ammonium cations Chemical class 0.000 description 17
- 239000004744 fabric Substances 0.000 description 16
- 125000000129 anionic group Chemical group 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 9
- XCYWUZHUTJDTGS-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-pyran Chemical compound COC1CCC=CO1 XCYWUZHUTJDTGS-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 5
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 5
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 5
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 5
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 5
- IAUGBVWVWDTCJV-UHFFFAOYSA-N 1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC(=O)C=C IAUGBVWVWDTCJV-UHFFFAOYSA-N 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
- KKSNTCYLMGYFFB-UHFFFAOYSA-N (prop-2-enoylamino)methanesulfonic acid Chemical compound OS(=O)(=O)CNC(=O)C=C KKSNTCYLMGYFFB-UHFFFAOYSA-N 0.000 description 3
- WXFWXFIWDGJRSC-UHFFFAOYSA-N 2,5-dimethoxy-2,5-dihydrofuran Chemical compound COC1OC(OC)C=C1 WXFWXFIWDGJRSC-UHFFFAOYSA-N 0.000 description 3
- NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 description 3
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 3
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- ZLPXFBBKYQYQEA-UHFFFAOYSA-N 1-(prop-2-enoylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(=O)C=C ZLPXFBBKYQYQEA-UHFFFAOYSA-N 0.000 description 2
- VDSAXHBDVIUOGV-UHFFFAOYSA-N 1-ethenyl-2-methyl-4,5-dihydroimidazole Chemical compound CC1=NCCN1C=C VDSAXHBDVIUOGV-UHFFFAOYSA-N 0.000 description 2
- HXVJQEGYAYABRY-UHFFFAOYSA-N 1-ethenyl-4,5-dihydroimidazole Chemical compound C=CN1CCN=C1 HXVJQEGYAYABRY-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 2
- WGESLFUSXZBFQF-UHFFFAOYSA-N n-methyl-n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCN(C)CC=C WGESLFUSXZBFQF-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- SJQBHNHASPQACB-ONEGZZNKSA-N (e)-1,2-dimethoxyethene Chemical group CO\C=C\OC SJQBHNHASPQACB-ONEGZZNKSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- SJQBHNHASPQACB-UHFFFAOYSA-N 1,2-dimethoxyethene Chemical compound COC=COC SJQBHNHASPQACB-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- RPYQPOCMVAEGHP-UHFFFAOYSA-N 2-ethenoxyacetic acid Chemical compound OC(=O)COC=C RPYQPOCMVAEGHP-UHFFFAOYSA-N 0.000 description 1
- GQWNPIKWYPQUPI-UHFFFAOYSA-N 2-methylbut-3-enoic acid Chemical compound C=CC(C)C(O)=O GQWNPIKWYPQUPI-UHFFFAOYSA-N 0.000 description 1
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
- OCXPJMSKLNNYLE-UHFFFAOYSA-N 2-prop-2-enylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)CC=C OCXPJMSKLNNYLE-UHFFFAOYSA-N 0.000 description 1
- CKSURTJJJBWBOU-UHFFFAOYSA-N 3-[(3-amino-3-imino-2-methylpropyl)diazenyl]-2-methylpropanimidamide;hydrochloride Chemical compound Cl.NC(=N)C(C)CN=NCC(C)C(N)=N CKSURTJJJBWBOU-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N aconitic acid Chemical compound OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- D06P1/44—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
- D06P1/52—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 synthetic macromolecular substances
- D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
- D06P1/5257—(Meth)acrylic acid
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/08—After-treatment with organic compounds macromolecular
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/93—Pretreatment before dyeing
Definitions
- the present invention relates to a process for the treatment of natural or synthetic polyamide fiber materials for improving the resistance of the dyes to ozone.
- Dyeing and printing with dyes often show high sensitivity to ozone.
- anthraquinone dyes are readily degraded by ozone oxidative and change in this way their Absorbtions and thus the color. This behavior is especially observed with blue anthraquinone dyes.
- the nuance of trichromatic dyeing based on blue anthraquinone dyes, for example a polyamide carpet fabric, is easily altered by ozone exposure. This deficiency is generally addressed by treating the dyed polyamide fiber material with phenol-formaldehyde condensate-based resins.
- the known ozone-resistance improving agents have disadvantages, e.g.
- Document WO-A-8 907 519 describes a process for fiber treatment to modify the fiber properties, in particular to increase the abrasion resistance of the material.
- the process is carried out in alkaline pH west, with a copolymer having latent carboxylic acid groups being applied to the substrate.
- the carboxyl groups of the polymer are complexed with di- or trivalent metal cations, amines or ammonium cations.
- the substrate is treated with an alkaline dispersion of the copolymer.
- the present invention therefore provides a process for improving the resistance of dyes to natural or synthetic polyamide fiber materials to ozone, characterized in that before, during or after dyeing the fiber material is treated with a liquor containing a homo- or copolymer having repeating structural units of the formula (1) wherein R 1 is optionally substituted C 1 -C 4 alkyl.
- R 1 may be, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, these alkyl radicals being unsubstituted or substituted, for example by halogen, such as fluorine, chlorine or bromine, hydroxy or sulfo.
- R 1 is preferably C 1 -C 4 -alkyl and especially methyl.
- the homopolymers or copolymers used according to the invention as agents for improving ozone resistance preferably contain from 50 to 100 mol% and in particular from 80 to 100 mol% of recurring structural units of the formula (1).
- the copolymerizable monomers used are, for example, anionic or non-ionic group-containing compounds in question.
- Preferred as copolymerizable monomers in the polymers used in the invention are Acrylic acid, maleic acid, vinylacetic acid, acrylamidoglycolic acid, (meth) acrylamidomethanesulfonic acid, vinylsulfonic acid, (meth) allylsulfonic acid, (meth) acrylamidomethylpropanesulfonic acid, (meth) acrylamidopropanesulfonic acid, (meth) acrylamidoethane-sulfonic acid, (meth) acrylamidomethanesulfonic acid, sulfopropyl (meth) acrylate, 4- Styrenesulfonic acid, maleic anhydride, N-vinylpyrrolidone, vinylcaprolactam, N-vinylformamide, N-vinyl-N-methyl-formamide, N-vinylacetamide, N-vinyl-N-methyl-acetamide, N-vinylimidazole, vinyl a
- the homopolymers or copolymers used in the process according to the invention have an average molecular weight of from 1 000 to 1 000 000, preferably from 1 000 to 500 000 and in particular from 5 000 to 200 000.
- the preparation of the homo- or copolymers used according to the invention as ozone-resistant agents containing recurring structural units of the formula (1) given above is carried out in a manner known per se, for example by ionic or preferably free-radical initiated polymerization of the monomers of the formula (2) in which R 1 has the meanings and preferences given above, for example in solution, suspension or emulsion, if appropriate in the presence of the unsaturated compounds mentioned above by way of example as copolymerizable monomers.
- the polymerization is preferably carried out in solution with a peroxide, persulfate or an azo compound, for example with sodium persulfate or azobis (2-amidinopropane) hydrochloride, as a radical chain initiator, this being, for example, in an amount of 0.005 to 10 wt.% on the monomers used, is present.
- a peroxide, persulfate or an azo compound for example with sodium persulfate or azobis (2-amidinopropane) hydrochloride, as a radical chain initiator, this being, for example, in an amount of 0.005 to 10 wt.% on the monomers used, is present.
- the homopolymers or copolymers used in the process according to the invention are used independently of the liquor ratio, e.g. in an amount of 0.05 to 10 wt .-%, preferably 0.1 to 6 wt .-% and particularly preferably 0.5 to 4 wt .-%, based on the weight of the polyamide fiber material used.
- the treatment of the polyamide fiber material with the homo- or copolymers used according to the invention can be carried out before, during or after the dyeing and preferably during or after the dyeing.
- the process according to the invention is advantageously carried out by adding the polymers to the dyeing liquor in the amount indicated above and dyeing the fiber material in the usual way.
- the process according to the invention is advantageously carried out by first dyeing the polyamide fiber material in a conventional manner and then aftertreating with a polymer containing the amount specified above fresh aqueous liquor. Thereafter, the dyed polyamide fiber material can be dewatered without further rinsing and dried in the usual way.
- the aftertreatment is usually done in fresh liquor. However, it can also be carried out directly in the dyebath, provided that the dyebath is at the end extensively stripped and still sufficiently acidic. After the treatment, water is usually rinsed briefly with cold water.
- polyamide fiber material natural polyamide fiber material such as e.g. Wool or silk, or synthetic polyamide fiber material, such as e.g. Polyamide 6 or polyamide 6.6, or fiber blends such as e.g. Wool / cellulose or polyamide / cellulose Mischfasem or polyamide / wool blended fibers into consideration.
- the fiber material is synthetic polyamide fiber material.
- the textile material can be used in any form, for example as fiber, yarn, woven or knitted fabric.
- the dyeings are carried out, for example, with anionic dyes, all conventional anionic dyes, e.g. as described in Color Index, 3rd edition (1971) and the supplements under the headings "Acid Dyes" are eligible.
- Examples are sulfo-containing monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine or formazan dyes.
- the dyeings are preferably carried out with anthraquinone dyes and in particular with blue anthraquinone dyes.
- the anionic dyes used to dye the polyamide fiber material are either in the form of their free sulfonic acid or, preferably, as their salts.
- suitable salts are the alkali metal, alkaline earth metal or ammonium salts or the salts of an organic amine. Examples which may be mentioned are the sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
- the anionic dyes used to dye the polyamide fiber material may contain other additives, e.g. Common salt or dextrin.
- the dyeing of the polyamide fiber material with anionic dyes can be carried out according to the dyeing or printing processes customary for these dyes, for example by the exhaustion process.
- the dyeing liquors or printing pastes can, in addition to water and the dyes, other additives, such as wetting agents, anti-foaming agents, leveling agents or the property of the textile material influencing agents such.
- anionic dyes used in the Därbebädem or printing pastes, depending on the desired color depth can vary within wide limits, in general, amounts of 0.01 to 15 wt .-%, in particular 0.01 to 10 wt. %, based on the Klarbegut or the printing paste, proved to be advantageous.
- Dyeing with anionic dyes takes place at a pH of from 2 to 7, in particular from 4 to 7, dyeing in the presence of the homo- or copolymers used according to the invention at a pH of from 2 to 7 and in particular from 4 to 7.
- the liquor ratio can be chosen within a wide range, e.g. from 1: 5 to 1:50, preferably 1: 5 to 1:30.
- the aftertreatment with the homo- or copolymers used according to the invention is preferably carried out by the exhaustion process.
- the liquor ratio can be chosen within a wide range and is e.g. 1: 4 to 1: 100, preferably 1:10 to 1:40 and especially 1: 5 to 1:40.
- Special devices are not required. It can e.g. the usual dyeing machines, e.g. open baths, winch skids, jiggers or paddles, jet or circulating apparatus.
- the treatment time may e.g. 10 to 60 minutes and preferably 15 to 40 minutes.
- the pH of the liquor is from 2 to 7, preferably from 4 to 7 and in particular from 4 to 6.
- the liquor may contain, besides the fixing agent, other usual additives, e.g. Electrolytes such as e.g. Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
- Electrolytes such as e.g. Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
- Example 1 68.8 parts of methacrylic acid, 4.4 parts of mercaptoethanol and 146 parts of water are placed in a reactor. Under nitrogen, the temperature is brought to 75 ° C. A solution of 1 part of sodium persulfate and 10 parts of water is added dropwise within 30 minutes. The reaction is exothermic and the temperature rises to 85 ° C. The mixture is postpolymerized at 85 ° C. for one hour. At 80 ° C is then added 13.8 parts of hydrogen peroxide 30% and stirred for 2 hours at this temperature. The polymer solution is cooled, brought to a pH of 6.5 and concentrated to a solids content of 40%. 210 g of a clear, light yellow viscous solution of a polymer which essentially contains structural units of the formula (101) are obtained. and has a molecular weight of about 8,000.
- EXAMPLE 2 A reactor is charged with 65 parts of isopropanol and 17.5 parts of water and heated under nitrogen to 80.degree. Then, a solution of 64.5 parts of methacrylic acid, 10.3 parts of 2-acrylamido-2-methyl-propanesulfonic acid and 22.5 parts of water is added dropwise within 120 minutes. At the same time, a solution of 8.3 parts of sodium persulfate and 25 parts of water is added dropwise within 150 minutes. It is postpolymerized for 3 hours at about 80 ° C. The polymer solution is diluted with water, the isopropanol distilled off and concentrated to a solids content of 20%. About 400 g of a cloudy, viscous solution of a polymer which consists essentially of structural units of the formulas (101) and (102) are obtained. having a Brookfield viscosity of 1600 cP.
- Example 3 69.5 parts of isopropanol and 19 parts of water are placed in a reactor and heated to 80 ° C. under nitrogen. Then, a solution of 64.5 parts of methacrylic acid, 21.7 parts of a 30% aqueous vinylsulfonic acid sodium salt solution, 69.3 parts of isopropanol and 140.7 parts of water is added dropwise within 120 minutes. At the same time, a solution of 7.5 parts of sodium persulfate and 25 parts of water is added dropwise within 150 minutes. It is postpolymerized for 3 hours at about 80 ° C. The polymer solution is diluted with water, the isopropanol distilled off and concentrated to a solids content of 30%. About 260 g of a cloudy, viscous solution of a polymer which comprises essentially structural units of the formulas (101) and (103) are obtained. having a Brookfield viscosity of 970 cP.
- Example 4 5.25 parts of 2-methoxy-3,4-dihydro-2H-pyran and 12 parts of o-xylene are placed in a reactor and heated to 90 ° C. under nitrogen. Then, a solution of 35 parts of methacrylic acid and 20 parts of o-xylene is added dropwise within 100 minutes. At the same time 0.8 parts of tert-butyl 2-ethyl-perhexanoate and 20 parts of o-xylene are added dropwise within 120 minutes. It is postpolymerized for 2 hours at about 90 ° C. The polymer solution is diluted with water and the o-xylene distilled off azeotropically.
- the polymer solution is adjusted to a pH of 7 and to a dry content of 20% concentrated.
- About 180 g of a clear, slightly viscous solution of a polymer comprising essentially structural units of the formulas (101) and (104) are obtained. having a Brookfield viscosity of 30 cP.
- Example 5 A dyebath containing 600 parts of water, 0.0108 parts of a dye of the formula 0.0135 parts of a dye of the formula and 0.033 parts of a dye of the formula is adjusted to a pH of 6.5 with 0.72 part of sodium dihydrogen phosphate monohydrate and 0.6 part of disodium hydrogen phosphate dodecahydrate.
- this dyebath is at 30 ° C with 30 parts of polyamide carpet fabric (polyamide 6). The temperature is increased uniformly within 45 minutes to the boiling point and then dyed for a further 30 minutes at this temperature. The gray-colored carpet is then rinsed.
- the dyed carpet fabric is washed in a fresh bath of 600 parts of water, 1.5 parts of the polymer solution according to Example 1 (amount used 2 wt .-% polymer based on the carpet fabric), 0.6 parts of sodium acetate and 0.7 parts of acetic acid at pH of 4.5 and a temperature of 75 ° C treated for 15 minutes.
- the carpet fabric is then rinsed and dried.
- the ozone fastness of the dyeing obtained is carried out according to the test specification ISO 105-G03.
- the comparison of the aftertreated carpet fabric with a carpet fabric that has not been post-treated shows a significant increase in the ozone resistance of the aftertreated carpet fabric.
- Example 5 The procedure is as described in Example 5, but instead of 2 wt .-%, based on the carpet fabric, of the polymer according to Example 1, the equivalent amount one of the polymers according to one of Examples 2 to 4, so also a polyamide carpet fabric is obtained with a gray, ozoneraum coloring.
- Example 6 A dyebath containing 600 parts of water,
- Example 6 If the procedure described in Example 6, but instead of 2 wt .-%, based on the carpet fabric, of the polymer according to Example 1, the equivalent amount of one of the polymers according to one of Examples 2 to 4, so also a polyamide carpet fabric with a gray Obtained ozone fast staining.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99810385A EP0957197B1 (de) | 1998-05-13 | 1999-05-04 | Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98810433 | 1998-05-13 | ||
EP98810433 | 1998-05-13 | ||
EP99810385A EP0957197B1 (de) | 1998-05-13 | 1999-05-04 | Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0957197A1 EP0957197A1 (de) | 1999-11-17 |
EP0957197B1 true EP0957197B1 (de) | 2006-06-21 |
Family
ID=8236082
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99810385A Expired - Lifetime EP0957197B1 (de) | 1998-05-13 | 1999-05-04 | Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien |
Country Status (8)
Country | Link |
---|---|
US (1) | US6280482B1 (xx) |
EP (1) | EP0957197B1 (xx) |
JP (1) | JP4443669B2 (xx) |
AU (1) | AU751951B2 (xx) |
CA (1) | CA2271873A1 (xx) |
DE (1) | DE59913578D1 (xx) |
DK (1) | DK0957197T3 (xx) |
ZA (1) | ZA993274B (xx) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59913578D1 (de) * | 1998-05-13 | 2006-08-03 | Ciba Sc Holding Ag | Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien |
US20030165404A1 (en) * | 2000-06-05 | 2003-09-04 | Takeshi Omatsu | Ozone indicator and method of measuring ozone concentration |
WO2003041639A2 (en) * | 2001-10-30 | 2003-05-22 | Microbiotix, Inc. | Methods and compositions for treating rotavirus-mediated disease |
US7090704B2 (en) * | 2001-12-05 | 2006-08-15 | Ciba Specialty Chemicals Corporation | Method of treating natural or synthetic polyamide fibre materials |
JP2007321247A (ja) * | 2006-05-30 | 2007-12-13 | Seiren Co Ltd | ポリアミド系繊維構造物 |
CN110882680A (zh) * | 2019-12-05 | 2020-03-17 | 广东海纳新材料科技有限公司 | 一种疏水矿化废弃纤维吸附材料的制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1254743A (en) * | 1969-06-16 | 1971-11-24 | Textilmaschb Zittau Veb | Application of dyestuffs to napped and pile textiles |
US3984202A (en) * | 1972-02-14 | 1976-10-05 | Allied Chemical Corporation | Alkanolamines to reduce ozone attack on dyes in polyamide fibers |
US4097546A (en) * | 1976-03-30 | 1978-06-27 | Allied Chemical Corporation | Ozone resistant, cationic dyeable nylon containing lithium, magnesium or calcium salts of sulfonated polystyrene copolymers |
CH642806B (de) * | 1978-07-07 | Sandoz Ag | Verfahren zum faerben oder bedrucken von cellulosehaltigen textilmaterialien mit reaktivfarbstoffen. | |
KR900700281A (ko) * | 1988-02-17 | 1990-08-13 | 리챠드 지. 워터맨 | 섬유 또는 직물 처리용 중합체 염 착물 |
US4822373A (en) | 1988-03-11 | 1989-04-18 | Minnesota Mining And Manufacturing Company | Process for providing polyamide materials with stain resistance with sulfonated novolak resin and polymethacrylic acd |
US4937123A (en) | 1988-03-11 | 1990-06-26 | Minnesota Mining And Manufacturing Company | Process for providing polyamide materials with stain resistance |
US5464452A (en) * | 1994-05-10 | 1995-11-07 | Henkel Corporation | Process for fixing dyes in textile materials |
EP0812949A3 (de) | 1996-06-11 | 1998-07-22 | Ciba SC Holding AG | Verfahren zur Behandlung von gefärbtem Cellulosefasermaterial |
EP0824155A1 (de) * | 1996-08-15 | 1998-02-18 | Clariant Finance (BVI) Limited | Wässrige, konzentrierte Polycarbonsäurenatriumsalz-Lösungen, deren Herstellung und Verwendung |
JPH1096180A (ja) | 1996-08-15 | 1998-04-14 | Clariant Internatl Ltd | ポリカルボン酸ナトリウム塩の濃厚な水溶液及びその使用方法 |
US5948125A (en) | 1997-05-20 | 1999-09-07 | Ciba Specialty Chemicals Corporation | Method of treating dyed, natural or synthetic polyamide fibre materials |
DE59913578D1 (de) * | 1998-05-13 | 2006-08-03 | Ciba Sc Holding Ag | Verfahren zur Behandlung von natürlichen oder synthetischen Polyamidfasermaterialien |
-
1999
- 1999-05-04 DE DE59913578T patent/DE59913578D1/de not_active Expired - Lifetime
- 1999-05-04 DK DK99810385T patent/DK0957197T3/da active
- 1999-05-04 EP EP99810385A patent/EP0957197B1/de not_active Expired - Lifetime
- 1999-05-11 CA CA002271873A patent/CA2271873A1/en not_active Abandoned
- 1999-05-11 JP JP12942399A patent/JP4443669B2/ja not_active Expired - Fee Related
- 1999-05-12 ZA ZA9903274A patent/ZA993274B/xx unknown
- 1999-05-12 AU AU28102/99A patent/AU751951B2/en not_active Ceased
-
2000
- 2000-07-05 US US09/609,955 patent/US6280482B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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AU2810299A (en) | 1999-11-25 |
US6280482B1 (en) | 2001-08-28 |
DE59913578D1 (de) | 2006-08-03 |
JPH11350354A (ja) | 1999-12-21 |
EP0957197A1 (de) | 1999-11-17 |
JP4443669B2 (ja) | 2010-03-31 |
AU751951B2 (en) | 2002-09-05 |
DK0957197T3 (da) | 2006-10-09 |
CA2271873A1 (en) | 1999-11-13 |
ZA993274B (en) | 1999-11-15 |
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