EP0957197A1 - Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique - Google Patents
Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique Download PDFInfo
- Publication number
- EP0957197A1 EP0957197A1 EP99810385A EP99810385A EP0957197A1 EP 0957197 A1 EP0957197 A1 EP 0957197A1 EP 99810385 A EP99810385 A EP 99810385A EP 99810385 A EP99810385 A EP 99810385A EP 0957197 A1 EP0957197 A1 EP 0957197A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- homo
- parts
- dyes
- fiber material
- 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
- 239000004952 Polyamide Substances 0.000 title claims abstract description 32
- 229920002647 polyamide Polymers 0.000 title claims abstract description 32
- 239000002657 fibrous material Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000000975 dye Substances 0.000 claims abstract description 39
- 229920001577 copolymer Polymers 0.000 claims abstract description 23
- 238000004043 dyeing Methods 0.000 claims abstract description 23
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001000 anthraquinone dye Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000004744 fabric Substances 0.000 description 16
- -1 alkyl radicals Chemical class 0.000 description 14
- 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
- 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
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- XCYWUZHUTJDTGS-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-pyran Chemical compound COC1CCC=CO1 XCYWUZHUTJDTGS-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 150000003839 salts Chemical class 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
- 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 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229940078552 o-xylene Drugs 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
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 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
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 3
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 3
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 3
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001252 acrylic acid derivatives 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
- 150000007942 carboxylates Chemical class 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
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000006116 polymerization reaction 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
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 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
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- SJQBHNHASPQACB-ONEGZZNKSA-N (e)-1,2-dimethoxyethene Chemical group CO\C=C\OC SJQBHNHASPQACB-ONEGZZNKSA-N 0.000 description 1
- VDSAXHBDVIUOGV-UHFFFAOYSA-N 1-ethenyl-2-methyl-4,5-dihydroimidazole Chemical compound CC1=NCCN1C=C VDSAXHBDVIUOGV-UHFFFAOYSA-N 0.000 description 1
- HXVJQEGYAYABRY-UHFFFAOYSA-N 1-ethenyl-4,5-dihydroimidazole Chemical compound C=CN1CCN=C1 HXVJQEGYAYABRY-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-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
- WXFWXFIWDGJRSC-UHFFFAOYSA-N 2,5-dimethoxy-2,5-dihydrofuran Chemical compound COC1OC(OC)C=C1 WXFWXFIWDGJRSC-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- QXWUJRONCAPLLL-UHFFFAOYSA-N 2-prop-2-enoxyacetic acid Chemical compound OC(=O)COCC=C QXWUJRONCAPLLL-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
- ZDZVKPXKLLLOOA-UHFFFAOYSA-N Allylmalonic acid Chemical compound OC(=O)C(C(O)=O)CC=C ZDZVKPXKLLLOOA-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- 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
- 239000004902 Softening Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 238000010521 absorption reaction 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
- 229940091181 aconitic acid Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- 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
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 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
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000839 emulsion Substances 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
- 239000000834 fixative Substances 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
- 239000001530 fumaric acid Substances 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
- 125000003010 ionic group Chemical group 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
- 238000004519 manufacturing process Methods 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 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
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 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
- GORGQKRVQGXVEB-UHFFFAOYSA-N n-ethenyl-n-ethylacetamide Chemical compound CCN(C=C)C(C)=O GORGQKRVQGXVEB-UHFFFAOYSA-N 0.000 description 1
- 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 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
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-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
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- VEYCPJGKKJULEP-UHFFFAOYSA-N prop-2-enoic acid sulfuric acid Chemical compound OC(=O)C=C.OS(O)(=O)=O VEYCPJGKKJULEP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 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
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent 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
- 239000011780 sodium chloride Substances 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
- 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
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-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 method for the treatment of natural or synthetic polyamide fiber materials to improve the durability of the dyes against exposure to ozone.
- Dyes and prints with dyes often show a high sensitivity to Ozone.
- anthraquinone dyes are easily oxidatively degraded by ozone and in this way change their absorption behavior and thus the color. This Behavior is particularly observed with blue anthraquinone dyes.
- the nuance a trichromatic stain based on blue anthraquinone dyes, for example one Polyamide carpet fabric, is easily changed by exposure to ozone. You meet this deficiency in general by resinating the dyed polyamide fiber material treated on the basis of phenol-formaldehyde condensates.
- improvements in ozone resistance have disadvantages, e.g.
- the present invention therefore relates to a process for improving the resistance of dyes on natural or synthetic polyamide fiber materials to the effects of ozone, characterized in that the fiber material is treated with a liquor containing a homo- or copolymer with recurring structural units before, during or after dyeing of the formula (1) wherein R 1 is optionally substituted C 1 -C 4 alkyl.
- Suitable C 1 -C 4 alkyl for R 1 are, 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.
- They preferably contain according to the invention as agents for improving the Homo- or copolymers used 50 to 100 mol% and ozone resistance in particular 80 to 100 mol% of repeating structural units of the formula (1).
- polymers used according to the invention are copolymers, then come as copolymerizable monomers e.g. anionic or non-ionic groups containing compounds in question.
- the following unsaturated compounds may be mentioned as examples of monomers containing anionic groups: Acrylic acid, maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, vinyl acetic acid, vinyl oxyacetic acid, vinyl propionic acid, crotonic acid, aconitic acid, allylacetic acid, allyloxyacetic acid, ⁇ , ⁇ -dimethylacrylic acid, allylmalonic acid, allyloxymaloxy, allylacrylic acid, carboxylate, methacryloyloxyacyl, methacrylate, carboxylate Allyl succinic acid, acrylamidoglycolic acid, vinylsulfonic acid, (meth) allylsulfonic acid, (meth) acrylamidomethylpropanesulfonic acid, (meth) acrylamidopropanesulfonic acid, (meth) acrylamidoethanesulfonic acid, (meth) acrylamidomethanes
- unsaturated compounds may be mentioned as examples of monomers containing nonionic groups: Maleic anhydride, vinylcaprolactam, diallylamine, N-methyldiallylamine, N-ethyldiallylamine, N-vinylpyrrolidone, N-vinylformamide, N-vinyl acetamide, N-vinyl-N-methylformamide, N-vinyl-N-methyl-acetamide, N-vinyl N-ethyl-acetamide, N-vinylimidazole, N-vinyl-N-methyl-imidazole, N-vinylimidazoline, N-vinyl-2-methylimidazoline, N-vinylcaprolactam, vinyl acetate, vinyl propionate, vinyl butyrate, C 1 -C 22 alkyl vinyl ketone, C 1 -C 22 alkyl vinyl ether, olefins such as ethylene, propylene, isobutene, styrene
- Copolymerizable monomers in the polymers used according to the invention Acrylic acid, maleic acid, vinyl acetic acid, acrylamidoglycolic acid, (meth) acrylamidomethanesulfonic acid, vinylsulfonic acid, (meth) allylsulfonic acid, (meth) acrylamidomethylpropanesulfonic acid, (meth) acrylamidopropanesulfonic acid, (meth) acrylamidoethanesulfonic acid, (meth) acrylamidomethanesulfonic acid, sulfopropyl (st) sulfatonic acid, sulfopropyl (meth) acrylate sulfate, Maleic anhydride, N-vinylpyrrolidone, vinylcaprolactam, N-vinylformamide, N-vinyl-N-methylformamide, N-vinyl acetamide, N-vinyl-N-methyl-acetamide
- Very particularly preferred as copolymerizable monomers in the polymers used according to the invention are: Vinylsulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 3- (meth) acrylamidopropanesulfonic acid, maleic anhydride, N-vinylpyrrolidone, N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methyl-acetamide, N -Vinylimidazole, vinyl acetate, styrene, hydroxyethyl / propyl- (meth) acrylate, (meth) acrylic acid-C 1 -C 6 alkyl ester, (meth) acrylonitrile, (meth) acrylamide, N-mono / N, N-di -C 1 -C 6 alkyl- (meth) acrylamide or 2-methoxy-3,4-dihydro-2H-pyran.
- Particularly important as copolymerizable monomers in the polymers used according to the invention are: Vinylsulfonic acid, 3- (meth) acrylamidopropanesulfonic acid or 2-methoxy-3,4-dihydro-2H-pyran.
- the homopolymers or copolymers used in the process according to the invention have average molecular weight of 1,000 to 1,000,000, preferably 1,000 to 500,000 and in particular 5,000 to 200,000.
- the homopolymers or copolymers containing recurring structural units of the above formula (1) used according to the invention as agents for improving the ozone resistance are prepared in a manner known per se, for example by polymerization of the monomers of the formula (2) initiated ionically or preferably by free radicals.
- R 1 has the meanings and preferences given above, for example in solution, suspension or emulsion, optionally in the presence of the unsaturated compounds mentioned above as examples of copolymerizable monomers.
- the polymerization is preferably carried out in solution with a peroxide, persulfate or an azo compound, for example with sodium persulfate or azo-bis- (2-amidinopropane) hydrochloride, as a free-radical initiator, for example in an amount of 0.005 to 10% by weight, based on the monomers used, is present.
- a peroxide, persulfate or an azo compound for example with sodium persulfate or azo-bis- (2-amidinopropane) hydrochloride, as a free-radical initiator, for example in an amount of 0.005 to 10% by weight, based on the monomers used, is present.
- the homo- or copolymers used in the process according to the invention are regardless of the fleet ratio e.g. in an amount of 0.05 to 10% by weight, preferably 0.1 to 6% by weight and particularly preferably 0.5 to 4% by weight, based on the weight of the polyamide fiber material used.
- Treatment of the polyamide fiber material with the homo- or copolymers can be before, during or after dyeing and preferably during or after dyeing.
- the polyamide fiber material is treated with those used according to the invention Homopolymers or copolymers during the dyeing process, that's how it is done Process according to the invention advantageously such that the polymers of Dyeing liquor is added in the amount specified above and the fiber material in the usual way Way colors.
- the polyamide fiber material is treated with those used according to the invention Homopolymers or copolymers after dyeing, this is done according to the invention Process advantageously such that the polyamide fiber material is first in usually colors and then an aftertreatment with a polymer in the connects the previously specified amount containing fresh aqueous liquor. After that the dyed polyamide fiber material can be dewatered and opened without further rinsing can be dried in the usual way.
- the after-treatment is usually carried out in a fresh one Fleet. However, it can also be carried out directly in the dye bath, provided that the dye bath is at the end largely stripped and is still sufficiently acidic. After the treatment is usually rinsed briefly with water.
- Natural polyamide fiber material such as e.g. Wool or Silk, or synthetic polyamide fiber material, e.g. Polyamide 6 or polyamide 6.6, or fiber mixtures such as Wool / cellulose or polyamide / cellulose mixed fibers or Polyamide / wool mixed fibers into consideration.
- the fiber material is preferred around synthetic polyamide fiber material.
- the textile can be used in any form, e.g. as fiber, yarn, woven or knitted fabric.
- the dyeings are carried out, for example, with anionic dyes, all of the usual anionic dyes, e.g. as in Color Index, 3rd edition (1971) and the Addenda to this are described under the heading "Acid Dyes”.
- Examples are sulfo group-containing monoazo, polyazo, metal complex azo, anthraquinone, Phthalocyanine or formazan dyes.
- the dyeings are preferably carried out using anthraquinone dyes and in particular blue ones Anthraquinone dyes.
- the anionic dyes used to dye the polyamide fiber material lie either in the form of their free sulfonic acid or preferably as their salts.
- the salts include, for example, the alkali, alkaline earth or ammonium salts or the salts an organic amine.
- Examples include sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
- the anionic dyes used to dye the polyamide fiber material can other additives, e.g. Cooking salt or dextrin.
- the dyeing of the polyamide fiber material with anionic dyes can be carried out according to the these dyes usual dyeing or printing processes, for example according to Pull-out procedure.
- the dyeing liquors or printing pastes can also Water and the dyes further additives, for example wetting agents, anti-foaming agents, Leveling agents or agents influencing the property of the textile material, e.g. Plasticizers, additives for flame retardant or dirt, water and oil repellent Agents and water softening agents and natural or synthetic Thickeners, e.g. Alginates and cellulose ethers.
- the amounts of anionic dyes in the dye baths or printing pastes can be used within wide limits depending on the desired depth of color fluctuate, in general amounts have from 0.01 to 15% by weight, in particular 0.01 up to 10% by weight, based on the dye material or the printing paste, has proven to be advantageous.
- the dyeing is preferably carried out with anionic dyes at a pH of 3 to 7, in particular 4 to 7, one used in the presence of those according to the invention Homo- or copolymers preferably at a pH of 2 to 7 and especially 4 to 7 colors.
- the liquor ratio can be chosen within a wide range, e.g. from 1: 5 to 1:50, preferably 1: 5 to 1:30. It is preferred to dye at a temperature from 70 to 110 ° C, in particular 80 to 105 ° C, wherein in the presence of the invention homo- or copolymers used preferably at 50 to 100 ° C and in particular is dyed at 80 to 100 ° C.
- the aftertreatment with the homo- or copolymers used according to the invention preferably takes place using the pull-out method.
- the fleet ratio can be within a wide range can be selected and is e.g. 1: 4 to 1: 100, preferably 1:10 to 1:40 and especially 1: 5 to 1:40.
- Dyeing machines e.g. open baths, reel runners, jigger or paddle, jet or Circulators can be used.
- the treatment time can e.g. 10 to 60 minutes and preferably 15 to 40 minutes.
- the pH of the fleet is usually included 2 to 7, preferably 4 to 7 and in particular 4 to 6.
- the liquor can contain other conventional additives, e.g. Electrolytes such as Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
- Electrolytes such as Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
- the process according to the invention gives dyeings or prints of Dyes, e.g. anionic dyes, on polyamide fiber material, which a have significant improvement in ozone fastness, without the color yield, nuance or the light fastness can be negatively affected.
- Dyes e.g. anionic dyes
- a dye bath 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 parts of sodium dihydrogenphosphate monohydrate and 0.6 part of disodium hydrogenphosphate dodecahydrate.
- This dye bath is mixed with 30 parts of polyamide carpet fabric (polyamide 6) at 30 ° C. The temperature is raised uniformly to the boiling point within 45 minutes and dyeing is then carried out for a further 30 minutes at this temperature. The gray colored carpet is then rinsed.
- the dyed carpet fabric is in a fresh bath from 600 parts of water, 1.5 parts of the polymer solution according to Example 1 (amount of 2 wt .-% polymer based on the carpet fabric), 0.6 parts of sodium acetate and 0.7 parts of acetic acid at a pH of 4.5 and a temperature of 75 ° C for 15 minutes.
- the carpet fabric is then rinsed and dried.
- the ozone fastness of the dyeing obtained is carried out in accordance with the test specification ISO 105-G03. The comparison of the after-treated carpet fabric with a carpet fabric that was not after-treated shows a significant increase in the ozone resistance of the after-treated carpet fabric.
- Example 5 The procedure is as described in Example 5, but instead of 2% by weight, based on the carpet fabric, the polymer according to Example 1, the equivalent amount one of the polymers according to one of Examples 2 to 4, is also a Obtain polyamide carpet fabric with a gray, ozone-resistant color.
- a dye bath 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 and 1.5 parts of the polymer solution from Example 1 (amount used 2% by weight) is adjusted to a pH of 6.5 using 0.72 part of sodium dihydrogenphosphate monohydrate and 0.6 part of disodium hydrogenphosphate dodecahydrate.
- This dye bath is mixed with 30 parts of polyamide carpet fabric (polyamide 6) at 30 ° C. The temperature is raised uniformly to the boiling point within 45 minutes and dyeing is then carried out for a further 30 minutes at this temperature. The gray colored carpet is then rinsed briefly with cold water and dried.
- the ozone fastness of the dyeing obtained is carried out in accordance with the test specification ISO 105-G03.
- the comparison of the dyed carpet fabric with a carpet fabric which was not dyed in the presence of the polymer solution from Example 1 shows a significant increase in the resistance to ozone.
- Example 6 The procedure is as described in Example 6, but instead of 2% by weight, based on the carpet fabric, the polymer according to Example 1, the equivalent amount one of the polymers according to one of Examples 2 to 4, is also a Obtain polyamide carpet fabric with a gray, ozone-resistant color.
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 (fr) | 1998-05-13 | 1999-05-04 | Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98810433 | 1998-05-13 | ||
EP98810433 | 1998-05-13 | ||
EP99810385A EP0957197B1 (fr) | 1998-05-13 | 1999-05-04 | Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0957197A1 true EP0957197A1 (fr) | 1999-11-17 |
EP0957197B1 EP0957197B1 (fr) | 2006-06-21 |
Family
ID=8236082
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99810385A Expired - Lifetime EP0957197B1 (fr) | 1998-05-13 | 1999-05-04 | Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique |
Country Status (8)
Country | Link |
---|---|
US (1) | US6280482B1 (fr) |
EP (1) | EP0957197B1 (fr) |
JP (1) | JP4443669B2 (fr) |
AU (1) | AU751951B2 (fr) |
CA (1) | CA2271873A1 (fr) |
DE (1) | DE59913578D1 (fr) |
DK (1) | DK0957197T3 (fr) |
ZA (1) | ZA993274B (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003041639A2 (fr) * | 2001-10-30 | 2003-05-22 | Microbiotix, Inc. | Methodes et preparations pour le traitement de maladies a rotavirus |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0957197B1 (fr) * | 1998-05-13 | 2006-06-21 | Ciba SC Holding AG | Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique |
US20030165404A1 (en) * | 2000-06-05 | 2003-09-04 | Takeshi Omatsu | Ozone indicator and method of measuring ozone concentration |
ATE330058T1 (de) * | 2001-12-05 | 2006-07-15 | Ciba Sc Holding Ag | Verfahren zur behandlung von natürlichen oder synthetischen polyamidfasermaterialien |
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 |
Citations (7)
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---|---|---|---|---|
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 |
GB2024874A (en) * | 1978-07-07 | 1980-01-16 | Sandoz Ltd | After treatment of cellulosic fibres dyed with reactive dyes |
WO1989007519A1 (fr) * | 1988-02-17 | 1989-08-24 | The Dow Chemical Company | Complexe de polymeres et de sels servant au traitement de fibres ou de tissus |
US5464452A (en) * | 1994-05-10 | 1995-11-07 | Henkel Corporation | Process for fixing dyes in textile materials |
EP0824155A1 (fr) * | 1996-08-15 | 1998-02-18 | Clariant Finance (BVI) Limited | Solutions aqueuses concentrées de sels de sodium d'acides polycarboxyliques, leur préparation et leur utilisation |
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---|---|---|---|---|
US4937123A (en) | 1988-03-11 | 1990-06-26 | Minnesota Mining And Manufacturing Company | Process for providing polyamide materials with stain resistance |
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 |
EP0812949A3 (fr) | 1996-06-11 | 1998-07-22 | Ciba SC Holding AG | Procédé pour traiter des matériaux fibreux cellulosiques teints |
CA2213172A1 (fr) | 1996-08-15 | 1998-02-15 | Clariant Finance (Bvi) Limited | Solutions aqueuses concentrees d'acide carboxylique et de sel de sodium, leur production et leur utilisation |
US5948125A (en) | 1997-05-20 | 1999-09-07 | Ciba Specialty Chemicals Corporation | Method of treating dyed, natural or synthetic polyamide fibre materials |
EP0957197B1 (fr) * | 1998-05-13 | 2006-06-21 | Ciba SC Holding AG | Procédé de traitement de matériaux fibreux en polyamide naturel ou synthétique |
-
1999
- 1999-05-04 EP EP99810385A patent/EP0957197B1/fr not_active Expired - Lifetime
- 1999-05-04 DE DE59913578T patent/DE59913578D1/de not_active Expired - Lifetime
- 1999-05-04 DK DK99810385T patent/DK0957197T3/da active
- 1999-05-11 JP JP12942399A patent/JP4443669B2/ja not_active Expired - Fee Related
- 1999-05-11 CA CA002271873A patent/CA2271873A1/fr not_active Abandoned
- 1999-05-12 AU AU28102/99A patent/AU751951B2/en not_active Ceased
- 1999-05-12 ZA ZA9903274A patent/ZA993274B/xx unknown
-
2000
- 2000-07-05 US US09/609,955 patent/US6280482B1/en not_active Expired - Fee Related
Patent Citations (7)
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 |
GB2024874A (en) * | 1978-07-07 | 1980-01-16 | Sandoz Ltd | After treatment of cellulosic fibres dyed with reactive dyes |
WO1989007519A1 (fr) * | 1988-02-17 | 1989-08-24 | The Dow Chemical Company | Complexe de polymeres et de sels servant au traitement de fibres ou de tissus |
US5464452A (en) * | 1994-05-10 | 1995-11-07 | Henkel Corporation | Process for fixing dyes in textile materials |
EP0824155A1 (fr) * | 1996-08-15 | 1998-02-18 | Clariant Finance (BVI) Limited | Solutions aqueuses concentrées de sels de sodium d'acides polycarboxyliques, leur préparation et leur utilisation |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003041639A2 (fr) * | 2001-10-30 | 2003-05-22 | Microbiotix, Inc. | Methodes et preparations pour le traitement de maladies a rotavirus |
WO2003041639A3 (fr) * | 2001-10-30 | 2003-07-24 | Microbiotix Inc | Methodes et preparations pour le traitement de maladies a rotavirus |
Also Published As
Publication number | Publication date |
---|---|
AU751951B2 (en) | 2002-09-05 |
CA2271873A1 (fr) | 1999-11-13 |
EP0957197B1 (fr) | 2006-06-21 |
AU2810299A (en) | 1999-11-25 |
JP4443669B2 (ja) | 2010-03-31 |
DE59913578D1 (de) | 2006-08-03 |
US6280482B1 (en) | 2001-08-28 |
JPH11350354A (ja) | 1999-12-21 |
ZA993274B (en) | 1999-11-15 |
DK0957197T3 (da) | 2006-10-09 |
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