EP0636743A2 - Process for dyeing of wool-containing fibre materials - Google Patents
Process for dyeing of wool-containing fibre materials Download PDFInfo
- Publication number
- EP0636743A2 EP0636743A2 EP94810425A EP94810425A EP0636743A2 EP 0636743 A2 EP0636743 A2 EP 0636743A2 EP 94810425 A EP94810425 A EP 94810425A EP 94810425 A EP94810425 A EP 94810425A EP 0636743 A2 EP0636743 A2 EP 0636743A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- wool
- remainder
- parts
- acid
- formula
- 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
- 210000002268 wool Anatomy 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004043 dyeing Methods 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 title claims abstract description 13
- 239000000835 fiber Substances 0.000 title description 7
- 239000000975 dye Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000002657 fibrous material Substances 0.000 claims abstract description 17
- 125000000129 anionic group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- -1 hydroxypropyl Chemical group 0.000 claims description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 15
- 239000011814 protection agent Substances 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 229920000151 polyglycol Polymers 0.000 claims description 7
- 239000010695 polyglycol Substances 0.000 claims description 7
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 6
- 150000004676 glycans Chemical class 0.000 claims description 6
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- 239000005017 polysaccharide Substances 0.000 claims description 6
- 229920002472 Starch Polymers 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
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- 235000019698 starch Nutrition 0.000 claims description 5
- 150000004043 trisaccharides Chemical class 0.000 claims description 5
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- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- 239000004386 Erythritol Substances 0.000 claims description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 2
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- 239000005715 Fructose Substances 0.000 claims description 2
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- 229930195725 Mannitol Natural products 0.000 claims description 2
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- 229940009714 erythritol Drugs 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims 1
- SZYKRTFCPGRTOA-ARJAWSKDSA-N (z)-2-(2-hydroxyethyl)but-2-enedioic acid Chemical compound OCC\C(C(O)=O)=C\C(O)=O SZYKRTFCPGRTOA-ARJAWSKDSA-N 0.000 claims 1
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims 1
- NJMYQRVWBCSLEU-UHFFFAOYSA-N 4-hydroxy-2-methylidenebutanoic acid Chemical compound OCCC(=C)C(O)=O NJMYQRVWBCSLEU-UHFFFAOYSA-N 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 abstract description 3
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- 230000006866 deterioration Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 15
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 12
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- 150000003254 radicals Chemical class 0.000 description 11
- 229910015900 BF3 Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 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
- 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 1
- 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 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
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-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
- QXWUJRONCAPLLL-UHFFFAOYSA-N 2-prop-2-enoxyacetic acid Chemical compound OC(=O)COCC=C QXWUJRONCAPLLL-UHFFFAOYSA-N 0.000 description 1
- CUTWSDAQYCQTGD-UHFFFAOYSA-N 2-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)C(C)OC(=O)C=C CUTWSDAQYCQTGD-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
- UMSFRTCUQPFZFA-UHFFFAOYSA-N 3-(3-sulfopropoxycarbonyl)but-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OCCCS(O)(=O)=O UMSFRTCUQPFZFA-UHFFFAOYSA-N 0.000 description 1
- ODAKQJVOEZMLOD-UHFFFAOYSA-N 3-[bis(carboxymethyl)amino]-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)CN(CC(O)=O)CC(O)=O ODAKQJVOEZMLOD-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 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
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application 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
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-L ethenyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-L 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- 125000001033 ether group Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229940089491 hydroxycitric acid Drugs 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 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
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 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
- 150000002772 monosaccharides Chemical class 0.000 description 1
- NZRFSLMXTFGVGZ-UHFFFAOYSA-N n-[diethylamino(prop-2-enoxy)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)OCC=C NZRFSLMXTFGVGZ-UHFFFAOYSA-N 0.000 description 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- 150000005691 triesters Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
- D06P3/8242—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and 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
- 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
- D06P1/60—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 polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
Definitions
- R represents the remainder of a polyglycerol according to (e), it preferably has a molecular weight minus 5000.
- the hydroxyl groups of the polyglycerol are preferably partially or completely in the form of an ether of the formula (2) given above.
- the compounds of the formula (1) used according to the invention can be prepared in a manner known per se, for example by using a compound of the formula R - OH (7), wherein R has the meaning given above, with an epihalohydrin, preferably epibromohydrin or particularly preferably epichlorohydrin, optionally in the presence of a catalyst, for example boron trifluoride / diacetic acid, boron trifluoride ethyl etherate, SnCl4 or Zn (BF4) 2.
- a catalyst for example boron trifluoride / diacetic acid, boron trifluoride ethyl etherate, SnCl4 or Zn (BF4) 2.
- the compounds of formula (7) are known per se or can be obtained by methods known per se.
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
Description
Die vorliegende Erfindung betrifft ein neues Verfahren zum Hochtemperatur-Färben von Wolle oder wollhaltigen Fasermaterialien.The present invention relates to a new process for high-temperature dyeing wool or wool-containing fiber materials.
Es ist bekannt, Wolle oder wollhaltige Fasermaterialien in Gegenwart von Hilfsmitteln zu färben, um so Faserschädigungen entgegenzuwirken, welche insbesondere beim Hochtemperatur-Färben auftreten. Viele der bekannten Hilfsmittel enthalten Formaldehyd oder setzen beim Erhitzen Formaldehyd frei, was toxikologisch nicht unbedenklich ist.It is known to dye wool or wool-containing fiber materials in the presence of auxiliaries in order to counteract fiber damage which occurs in particular during high-temperature dyeing. Many of the known auxiliaries contain formaldehyde or release formaldehyde when heated, which is not toxicologically harmless.
Es wurde nun überraschend ein verbessertes Verfahren zum Hochtemperatur-Färben von wollhaltigen Fasermaterialien gefunden, welches auf der Verwendung einer neuen Klasse von Wollschutzmitteln basiert.Surprisingly, an improved process for high-temperature dyeing of wool-containing fiber materials has now been found, which is based on the use of a new class of wool protection agents.
Gegenstand der vorliegenden Erfindung ist somit ein Verfahren zum Färben von wollhaltigen Fasermaterialien mit anionischen Farbstoffen, welches dadurch gekennzeichnet ist, dass man diese Materialien in Gegenwart eines Wollschutzmittels enthaltend mindestens eine Verbindung der Formel
R-O-CH₂-CH(OH)-CH₂-Y (1),
worin Y Halogen bedeutet und R
- (a) der Rest einer hydroxygruppenhaltigen ethylenisch ungesättigten Verbindung,
- (b) der Rest eines Homo- oder Copolymerisats aus hydroxygruppenhaltigen ethylenisch ungesättigten Monomeren und gegebenenfalls einem oder mehreren Comonomeren,
- (c) der Rest eines Mono-, Di-, Tri-, Oligo- oder Polysaccharids,
- (d) der Rest einer hydroxygruppenhaltigen C₁-C₂₂-Alkylverbindung,
- (e) der Rest eines Polyglycerinderivats mit einem Molekulargewicht ≦ 50 000, oder
- (f) der Rest eines Polyglykols, ist
färbt.The present invention thus relates to a process for dyeing wool-containing fiber materials with anionic dyes, which is characterized in that these materials in the presence of a wool protection agent containing at least one compound of the formula
RO-CH₂-CH (OH) -CH₂-Y (1),
where Y is halogen and R
- (a) the remainder of a hydroxy group-containing ethylenically unsaturated compound,
- (b) the remainder of a homo- or copolymer of hydroxyl-containing ethylenically unsaturated monomers and optionally one or more comonomers,
- (c) the remainder of a mono-, di-, tri-, oligo- or polysaccharide,
- (d) the remainder of a hydroxy group-containing C₁-C₂₂ alkyl compound,
- (e) the remainder of a polyglycerol derivative with a molecular weight ≦ 50,000, or
- (f) the remainder of a polyglycol
colors.
Y steht z.B. für Brom und vorzugsweise für Chlor.Y stands e.g. for bromine and preferably for chlorine.
Weisen die oben genannten Reste (a) bis (f) weitere Hydroxygruppen auf, so können diese jeweils als freie Hydroxygruppe oder z.B. in Form einer Ethergruppierung der Formel
-O-CH₂-CH(OH)-CH₂-Y (2),
worin Y die oben angegebene Bedeutung hat, vorliegen. Im Rest R vorhandene weitere Hydroxygruppen können auch in ethoxylierter, propoxylierter oder 2-hydroxypropoxylierter Form, z.B. in Form eines Restes der Formel
-O-(CH₂CH₂O)x - H (3)
-O-(CH₂CH[CH₃]O)y - H (4)
oder
-O-(CH₂CH[OH]CH₂O)z - H (5),
worin x, y und z unabhängig voneinander je eine Zahl von z.B. 1 bis 200 bedeuten, vorliegen.If the abovementioned radicals (a) to (f) have further hydroxyl groups, these can each be in the form of a free hydroxyl group or, for example, in the form of an ether group of the formula
-O-CH₂-CH (OH) -CH₂-Y (2),
where Y has the meaning given above. Further hydroxyl groups present in the R radical can also be in ethoxylated, propoxylated or 2-hydroxypropoxylated form, for example in the form of a radical of the formula
-O- (CH₂CH₂O) x - H (3)
-O- (CH₂CH [CH₃] O) y - H (4)
or
-O- (CH₂CH [OH] CH₂O) z - H (5),
wherein x, y and z each independently represent a number from, for example, 1 to 200.
Steht R für den Rest einer hydroxygruppenhaltigen ethylenisch ungesättigten Verbindung gemäss (a), handelt es sich z.B. um den Rest von Allylalkohol oder um den Rest einer vollständig mit einer Hydroxy-C₁-C₄-Alkylverbindung oder mit einem C₂-C₄-Alkylenglykol veresterten ethylenisch ungesättigten Mono-, Di- oder Tricarbonsäure. Beispiele für solche ethylenisch ungesättigten Carbonsäurehydroxyalkylester sind die 2- oder 3-Hydroxypropylester oder Hydroxyethylester bzw. -di- oder triester von (Meth)Acrylsäure, Maleinsäure, Fumarsäure, Itaconsäure, Mesaconsäure, Citraconsäure, Vinylessigsäure, Vinylpropionsäure, Crotonsäure, Aconitsäure, Allylessigsäure, Vinyloxyessigsäure, Allyloxyessigsäure, α,β-Dimethyl(meth)acrylsäure, Methylenmalonsäure, 2-Hydroxy(meth)acrylsäure, 2-Halogeno(meth)acrylsäure, α-Carboxyethylacrylat, Acrylamidoglycolsäure, β-Carboxyethylacrylat, Allyloxy-3-hydroxy-butansäure, Allyloxymalonsäure, Allylbernsteinsäure oder Allylmalonsäure.R stands for the remainder of a hydroxy group-containing ethylenically unsaturated compound according to (a), it is for example the remainder of allyl alcohol or the remainder of an ethylenically unsaturated which is fully esterified with a hydroxy-C₁-C₄-alkyl compound or with a C₂-C₄-alkylene glycol Mono-, di- or tricarboxylic acid. Examples of such ethylenically unsaturated carboxylic acid hydroxyalkyl esters are the 2- or 3-hydroxypropyl esters or hydroxyethyl esters or -di- or triesters of (meth) acrylic acid, maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, vinyl acetic acid, vinyl propionic acid, crotonic acid, aconitic acid, allylacetic acid, acetic acid , Allyloxyacetic acid, α, β-dimethyl (meth) acrylic acid, methylene malonic acid, 2-hydroxy (meth) acrylic acid, 2-halogeno (meth) acrylic acid, α-carboxyethyl acrylate, acrylamidoglycolic acid, β-carboxyethyl acrylate, allyloxy-3-hydroxybutanoic acid, allyloxymalonic acid , Allylsuccinic acid or allylmalonic acid.
Bevorzugt steht R als hydroxygruppenhaltiger, ethylenisch ungesättigter Rest für den Rest von Allylalkohol, Acrylsäurehydroxypropyl- oder -hydroxyethylester, Methacrylsäurehydroxypropyl- oder -hydroxyethylester oder Maleinsäuredihydroxypropyl- oder -hydroxyethylester.R is preferably a hydroxyl-containing, ethylenically unsaturated radical for the remainder of allyl alcohol, hydroxypropyl or hydroxyethyl acrylate, hydroxypropyl or hydroxyl methacrylate or dihydroxypropyl or hydroxyl maleate.
Bedeutet R den Rest eines Homo- oder Copolymerisats gemäss (b), so steht R z.B. für den Rest eines Homo- oder Copolymerisats, welches aus einer oder mehreren der zuvor genannten hydroxygruppenhaltigen, α,β-ungesättigten Verbindungen und gegebenenenfalls einem oder mehreren copolymerisierbaren monoethylenisch ungesättigten Monomeren aufgebaut ist.If R represents the remainder of a homo- or copolymer according to (b), R is e.g. for the remainder of a homopolymer or copolymer which is composed of one or more of the abovementioned hydroxyl-containing, α, β-unsaturated compounds and, if appropriate, one or more copolymerizable monoethylenically unsaturated monomers.
Geeignete copolymerisierbare monoethylenisch ungesättigte Monomere sind z.B. Ester, Amide oder Nitrile von ungesättigten Carbonsäuren, z.B. Acrylsäuremethyl- oder ethylester, Methacrylsäuremethyl- oder ethylester, Hydroxyethyl(meth)acrylat, Hydroxypropyl(meth)acrylate, Hydroxybutyl(meth)acrylate, Dimethylaminoethyl(meth)acrylat, Diethylaminoethyl(meth)acrylat, Acrylamid, Methacrylamid, N-Alkyl(meth)acrylamide, Acrylnitril oder Methacrylnitril. Eine weitere Gruppe von geeigneten Comonomeren umfasst Sulfonsäuregruppen oder Phosphonsäuregruppe enthaltende Monomere, z.B. (Meth)Allylsulfonsäure, Vinylsulfonsäure, 3-Allyloxy-2-hydroxypropansulfonsäure, Styrolsulfonsäure, Acrylamidomethansulfonsäure, 3-Sulfopropyl(meth)acrylate, 3-Sulfopropylitaconate, 2-Acrylamido-2-methylpropansulfonsäure, Vinylphosphonat, Allylphosphonat und Acrylamidomethylpropanphosphonsäure. Ausserdem eignen sich als Monomere N-Vinylpyrrolidon, N-Vinylcaprolactam, N-Vinylformamid, N-Vinyl-N-methylformamid, N-Vinylacetamid, N-Vinyl-N-methylacetamid, N-Vinylimidazol, N-Vinylmethylimidazol, N-Vinyl-2-methylimidazol, N-Vinylimidazolin, Methylvinylketon, Vinylacetat, Vinylpropionat, Vinylbutyrat, Styrol, Olefine mit z.B. 2 bis 10 C-Atomen wie Ethylen, Propylen, Isobutylen, Hexen, Diisobuten und Vinylalkylether wie Metylvinylether, Ethylvinylether, Dimethoxyethylen, n-Butylvinylether, Isobutylvinylether, Hexylvinylether oder Octylvinylether, sowie Mischungen der genannten Monomere.Suitable copolymerizable monoethylenically unsaturated monomers are e.g. Esters, amides or nitriles of unsaturated carboxylic acids, e.g. Methyl or ethyl acrylate, methyl or ethyl methacrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, acrylamide, methacrylamide, N-alkyl (meth) acrylamides, acrylonitrile or methacrylonitrile. Another group of suitable comonomers includes sulfonic acid groups or monomers containing phosphonic acid group, e.g. (Meth) allylsulfonic acid, vinylsulfonic acid, 3-allyloxy-2-hydroxypropanesulfonic acid, styrene sulfonic acid, acrylamidomethanesulfonic acid, 3-sulfopropyl (meth) acrylates, 3-sulfopropyl itaconate, 2-acrylamido-2-methylpropanesulfonic acid, vinyl phosphonate, allyl phosphonate and acrylamidomethylpropane. Also suitable as monomers are N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methylacetamide, N-vinylimidazole, N-vinylmethylimidazole, N-vinyl-2 -methylimidazole, N-vinylimidazoline, methyl vinyl ketone, vinyl acetate, vinyl propionate, vinyl butyrate, styrene, olefins with, for example 2 to 10 carbon atoms such as ethylene, propylene, isobutylene, hexene, diisobutene and vinyl alkyl ethers such as methyl vinyl ether, ethyl vinyl ether, dimethoxyethylene, n-butyl vinyl ether, isobutyl vinyl ether, hexyl vinyl ether or octyl vinyl ether, and mixtures of the monomers mentioned.
Die R zugrunde liegenden Homo- und Copolymerisate weisen vorzugsweise ein Molekulargewicht von z.B. 100 bis 1000000, besonders bevorzugt von 100 bis 10 000 und insbesondere bevorzugt von 500 bis 5000, auf.The homopolymers and copolymers on which R is based preferably have a molecular weight of, for example, 100 to 1,000,000, particularly preferably from 100 to 10,000 and particularly preferably from 500 to 5,000.
Bedeutet R den Rest eines Mono-, Di-, Tri-, Oligo- oder Polysaccharids gemäss (c), so kommen hierbei alle üblichen Saccharide, wie sie aus den Lehrbüchern der organischen Chemie bekannt sind, in Frage. Beispiele für solche Saccharide sind Monosaccharide wie Pentosen, z.B. Arabinose, Xylose oder Ribose, oder Hexosen, z.B. Glucose, Mannose, Galactose oder Fructose, Di- Tri- und Oligosaccharide wie z.B. Saccharose, Milchzucker, Lactose, Maltose oder Raffinose oder Polysaccharide wie z.B. Stärke oder Cellulose. Bevorzugt steht R für den Rest von Stärke, deren Hydroxygruppen teilweise oder vollständig in Form eines Ethers der zuvor angegebenen Formel (2) vorliegen.If R is the remainder of a mono-, di-, tri-, oligo- or polysaccharide according to (c), all customary saccharides as are known from the textbooks of organic chemistry can be used. Examples of such saccharides are monosaccharides such as pentoses, e.g. Arabinose, xylose or ribose, or hexoses, e.g. Glucose, mannose, galactose or fructose, di-tri and oligosaccharides such as e.g. Sucrose, milk sugar, lactose, maltose or raffinose or polysaccharides such as e.g. Starch or cellulose. R is preferably the remainder of starch, the hydroxyl groups of which are partially or completely in the form of an ether of the formula (2) given above.
Bedeutet R den Rest einer hydroxygruppenhaltigen C₁-C₂₂-Alkylverbindung gemäss (d), handelt es sich z.B. um den Rest eines einwertigen Alkanols, z.B. um den Rest von Methanol, Ethanol, n- oder iso-Propanol, n-, iso-, sec.- oder tert.-Butanol oder um den Rest eines geradkettigen oder verzweigten C₅-C₂₂-Monoalkohols, um den Rest eines Glykols wie z.B. Ethylenglykol oder Propylenglykol oder um den Rest eines mehrwertigen Alkohols wie z.B. Glycerin, Diglycerin, Triglycerin, 1,1,1-Tris(hydroxymethyl)propan, Erythrit, Pentaerythrit, Arabit, Sorbit oder Mannit. Weisen die genannten Alkohole mehr als eine Hydroxygruppe auf, so können die weiteren Hydroxygruppen teilweise oder vollständig in Form eines Ethers der zuvor angegebenen Formel (2) oder als ethoxylierter, propoxylierter oder 2-hydroxypropoxylierter Rest der Formel (3), (4) oder (5) vorliegen.If R is the residue of a hydroxy group-containing C₁-C₂₂ alkyl compound according to (d), it is e.g. around the rest of a monohydric alkanol, e.g. around the rest of methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol or around the rest of a straight-chain or branched C₅-C₂₂ monoalcohol, around the rest of a glycol such as e.g. Ethylene glycol or propylene glycol or around the rest of a polyhydric alcohol such as e.g. Glycerin, diglycerin, triglycerin, 1,1,1-tris (hydroxymethyl) propane, erythritol, pentaerythritol, arabitol, sorbitol or mannitol. If the alcohols mentioned have more than one hydroxyl group, the further hydroxyl groups can be partially or completely in the form of an ether of the above formula (2) or as an ethoxylated, propoxylated or 2-hydroxypropoxylated radical of the formula (3), (4) or 5) are available.
R steht als hydroxygruppenhaltiger Alkylrest bevorzugt für den Rest eines mehrwertigen Alkohols, dessen Hydroxygruppen teilweise oder vollständig in Form eines Ethers der zuvor angegebenen Formel (2) oder als ethoxylierter, propoxylierter oder 2-hydroxypropoxylierter Rest der Formel (3), (4) oder (5) vorliegen. Beispiele für besonders bevorzugte Hydroxyalkylreste R sind der Rest von Glycerin, Diglycerin, Pentaerythrit und 1,1,1-Tris(hydroxymethyl)propan, worin die weiteren Hydroxygruppen teilweise oder vollständig in Form eines Ethers der zuvor angegebenen Formel (2) oder als ethoxylierter, propoxylierter oder 2-hydroxypropoxylierter Rest der Formel (3), (4) oder (5) vorliegen.R as the alkyl group containing hydroxy groups preferably represents the residue of a polyhydric alcohol, the hydroxyl groups of which are partially or completely in the form of an ether of the formula (2) given above or as an ethoxylated, propoxylated or 2-hydroxypropoxylated radical of the formula (3), (4) or ( 5) are available. Examples of particularly preferred hydroxyalkyl radicals R are the radical of glycerol, diglycerol, pentaerythritol and 1,1,1-tris (hydroxymethyl) propane, in which the further hydroxyl groups are partially or completely in the form of an ether of the formula (2) given above or as an ethoxylated, propoxylated or 2-hydroxypropoxylated radical of the formula (3), (4) or (5) are present.
Steht R für den Rest eines Polyglycerins gemäss (e), so weist dieses bevorzugt ein Molekulargewicht ≦ 5000 auf. Die Hydroxygruppen des Polyglycerins liegen bevorzugt teilweise oder vollständig in Form eines Ethers der zuvor angegebenen Formel (2) vor.If R represents the remainder of a polyglycerol according to (e), it preferably has a molecular weight gewicht 5000. The hydroxyl groups of the polyglycerol are preferably partially or completely in the form of an ether of the formula (2) given above.
Steht R für den Rest eines Polyglykols gemäss (f), so entspricht dieser z.B. der Formel
-(CH₂CH₂O)s - (CH₂CH[CH₃]O)t - H (6),
worin s und t unabhängig voneinander je eine Zahl von z.B. 0 bis 200 bedeuten und die Summe (s + t) ≧ 1 ist.If R represents the remainder of a polyglycol according to (f), this corresponds, for example, to the formula
- (CH₂CH₂O) s - (CH₂CH [CH₃] O) t - H (6),
where s and t each independently represent a number from, for example, 0 to 200 and the sum (s + t) ≧ 1.
Das Polyglykol weist z.B. ein Molekulargewicht von ≦ 100 000 und vorzugsweise ≦ 1 000 auf. Insbesondere bevorzugt steht R als Polyglykolrest für den Rest eines Polyethylenglykols mit einem Molekulargewicht von ≦ 1 000.The polyglycol e.g. a molecular weight of ≦ 100,000 and preferably ≦ 1,000. As a polyglycol radical, R particularly preferably represents the radical of a polyethylene glycol with a molecular weight of von 1,000.
Die erfindungsgemäss verwendeten Verwendeten Verbindungen der Formel (1) können in an sich bekannter Weise hergestellt werden, z.B. indem man eine Verbindung der Formel
R - OH (7),
worin R die zuvor angegebene Bedeutung hat, mit einem Epihalogenohydrin, vorzugsweise Epibromhydrin oder insbesondere bevorzugt Epichlorhydrin, gegebenenfalls in Gegenwart eines Katalysators, z.B. Bortrifluorid/Diessigsäure, Bortrifluorid-Ethyletherat, SnCl₄ oder Zn(BF₄)₂, umsetzt. Die Verbindungen der Formel (7) sind an sich bekannt oder können nach an sich bekannten Methoden erhalten werden.The compounds of the formula (1) used according to the invention can be prepared in a manner known per se, for example by using a compound of the formula
R - OH (7),
wherein R has the meaning given above, with an epihalohydrin, preferably epibromohydrin or particularly preferably epichlorohydrin, optionally in the presence of a catalyst, for example boron trifluoride / diacetic acid, boron trifluoride ethyl etherate, SnCl₄ or Zn (BF₄) ₂. The compounds of formula (7) are known per se or can be obtained by methods known per se.
Die erfindungsgemäss eingesetzten Wollschutzmittel können eine oder mehrere der Verbindungen der Formel (1) enthalten. Gute Ergebnisse werden auch erhalten, wenn man als Wollschutzmittel ein Gemisch enthaltend (I) eine oder mehrere Verbindungen der Formel (1) und (II) eine organische Mono-, Di- oder Tricarbonsäure, z.B. Essigsäure, Propionsäure, Bernsteinsäure, Isoserindiessigsäure, Nitrilotriessigsäure, Ethylendiamintriessigsäure, Diethylentriaminpentaessigsäure, Hydroxyethylendiaminotriessigsäure, Aepfelsäure, Citronensäure, Hydroxycitronensäure, Milchsäure, Tartronsäure oder Weinsäure, oder eine Mineralsäure, z.B. Salzsäure, Schwefelsäure, Phosphorsäure, verwendet.The wool protection agents used according to the invention can contain one or more of the compounds of the formula (1). Good results are also obtained if a mixture containing (I) one or more compounds of the formula (1) and (II) an organic mono-, di- or tricarboxylic acid, e.g. Acetic acid, propionic acid, succinic acid, isoserine diacetic acid, nitrilotriacetic acid, ethylenediaminetriacetic acid, diethylenetriaminepentaacetic acid, hydroxyethylenediaminotriesacetic acid, malic acid, citric acid, hydroxycitric acid, lactic acid, tartronic acid or tartaric acid, e.g. or a mineral acid Hydrochloric acid, sulfuric acid, phosphoric acid used.
Bevorzugte Ausführungsformen der vorliegenden Erfindung betreffen
- die Verwendung eines Wollschutzmittels enthaltend eine Verbindung der Formel (1), worin Y Chlor und R der Rest eines Mono-, Di-, Tri-, Oligo- oder Polysaccharids, der Rest einer hydroxygruppenhaltigen C₁-C₂₂-Alkylverbindung, der Rest eines Polyglycerinderivats mit einem Molekulargewicht ≦ 50 000, oder der Rest eines Polyglykols ist;
- die Verwendung eines Wollschutzmittels enthaltend eine Verbindung der Formel (1), worin Y Chlor und R der Rest eines Mono-, Di-, Tri-, Oligo- oder Polysaccharids, dessen Hydroxygruppen teilweise oder vollständig in Form des Ethers der Formel
- O - CH₂ - CH(OH) - CH₂ - Cl (2a)
vorliegen, ist; - die Verwendung eines Wollschutzmittels enthaltend eine Verbindung der Formel (1), worin Y Chlor und R der Rest eines mehrwertigen Alkohols, dessen Hydroxygruppen teilweise oder vollständig in Form des Ethers der zuvor angegebenen Formel (2a) oder als ethoxylierter, propoxylierter oder 2-hydroxypropoxylierter Rest der zuvor angegebenen Formel (3), (4) oder (5) vorliegen, ist;
- die Verwendung eines Wollschutzmittels enthaltend eine Verbindung der Formel (1), worin Y Chlor und R der Rest von Glycerin, Diglycerin, Pentaerythrit und 1,1,1-Tris(hydroxymethyl)propan, worin die weiteren Hydroxygruppen teilweise oder vollständig in Form eines Ethers der zuvor angegebenen Formel (2a) oder als ethoxylierter, propoxylierter oder 2-hydroxypropoxylierter Rest der Formel (3), (4) oder (5) vorliegen, ist;
- die Verwendung eines Wollschutzmittels enthaltend eine Verbindung der Formel (1), worin Y Chlor und R der Rest eines Polyethylenglykols mit einem Molekulargewicht ≦ 1000 ist.
- the use of a wool protection agent containing a compound of formula (1), wherein Y is chlorine and R is the rest of a mono-, di-, tri-, oligo- or polysaccharide, the rest of a hydroxy group-containing C₁-C₂₂-alkyl compound, the rest of a Polyglycerol derivative with a molecular weight ≦ 50,000, or the rest of a polyglycol;
- the use of a wool protection agent containing a compound of formula (1), wherein Y is chlorine and R is the rest of a mono-, di-, tri-, oligo- or polysaccharide, the hydroxyl groups of which are partially or completely in the form of the ether of the formula
- O - CH₂ - CH (OH) - CH₂ - Cl (2a)
is present; - the use of a wool protection agent containing a compound of formula (1), wherein Y is chlorine and R is the residue of a polyhydric alcohol, the hydroxyl groups of which are partially or completely in the form of the ether of the formula (2a) given above or as an ethoxylated, propoxylated or 2-hydroxypropoxylated residue of the aforementioned formula (3), (4) or (5) is present;
- the use of a wool protection agent containing a compound of formula (1) in which Y is chlorine and R is the rest of glycerol, diglycerol, pentaerythritol and 1,1,1-tris (hydroxymethyl) propane, in which the further hydroxyl groups are partially or completely in the form of an ether of the aforementioned formula (2a) or as an ethoxylated, propoxylated or 2-hydroxypropoxylated radical of the formula (3), (4) or (5);
- the use of a wool protection agent containing a compound of formula (1), wherein Y is chlorine and R is the rest of a polyethylene glycol with a molecular weight ≦ 1000.
Man geht z.B. so vor, dass man das wollhaltige Fasermaterial zuerst mit dem Wollschutzmittel in einem wässrigen Bad vorbehandelt und anschliessend durch Zugabe des Farbstoffs zu diesem Bad färbt. Man kann auch so vorgehen, dass man das Färbegut gleichzeitig mit dem Wollschutzmittel und dem Farbstoff in einem wässrigen Bad behandelt.One goes e.g. so that the wool-containing fiber material is first pretreated with the wool protection agent in an aqueous bath and then dyed by adding the dye to this bath. It is also possible to treat the material to be dyed simultaneously with the wool preservative and the dye in an aqueous bath.
Es hat sich als praktikabel erwiesen, das Wollschutzmittel in einer Menge von z.B. 0,5 bis 10 Gew.-%, vorzugsweise 1 bis 6 Gew.-%, bezogen auf das Gewicht des Färbeguts, einzusetzen.It has proven to be practical to use the wool protection agent in an amount of, for example, 0.5 to 10% by weight, preferably 1 to 6% by weight, based on the weight of the material to be dyed.
Bei dem wollhaltigen Fasermaterial kann es sich um Wolle allein oder um Mischungen aus z.B. Wolle/Polyamid oder Wolle/Polyester handeln. Dabei werden Gemische aus Wolle und synthetischem Polyamid vorzugsweise mit anionischen Farbstoffen und Gemische aus Wolle und Polyesterfasern vorzugsweise mit Dispersions- und anionischen Farbstoffen gefärbt. Geeignete anionische Farbstoffe und Dispersionsfarbstoffe sind dem Fachmann bekannt.The wool-containing fiber material can be wool alone or a mixture of e.g. Trade wool / polyamide or wool / polyester. Mixtures of wool and synthetic polyamide are preferably dyed with anionic dyes and mixtures of wool and polyester fibers are preferably dyed with disperse and anionic dyes. Suitable anionic dyes and disperse dyes are known to the person skilled in the art.
Das Fasermaterial kann in den verschiedensten Verarbeitungsstadien vorliegen, z.B. in Form von Garnen, Flocken, Kammzug, Maschenware, wie Strickware oder Gewirke, als Faservliesstoff oder vorzugsweise als Gewebe.The fiber material can be in various stages of processing, e.g. in the form of yarns, flakes, sliver, knitwear such as knitwear or knitted fabrics, as a nonwoven fabric or preferably as a woven fabric.
Bei den Mischfasermaterialien handelt es sich vorzugsweise um Fasermischungen aus Wolle und Polyester, die in der Regel in einem Teilverhältnis von 20 bis 50 Gewichtsteilen Wolle zu 80-50 Gewichtsteilen Polyester vorliegen. Die für das Verfahren bevorzugten Fasermischungen enthalten 45 Teile Wolle und 55 Teile Polyesterfasern.The mixed fiber materials are preferably fiber blends of wool and polyester, which are generally present in a proportion of 20 to 50 parts by weight of wool to 80-50 parts by weight of polyester. The fiber mixtures preferred for the process contain 45 parts of wool and 55 parts of polyester fibers.
Das Flottenverhältnis kann beim erfindungsgemässen Verfahren innerhalb eines weiten Bereiches gewählt werden; es beträgt z.B. 1:1 bis 1:100 und vorzugsweise 1:10 bis 1:50.The liquor ratio can be selected within a wide range in the process according to the invention; it is e.g. 1: 1 to 1: 100 and preferably 1:10 to 1:50.
Das Färbebad kann neben dem Farbstoff, Wasser und dem Wollhilfsmittel weitere übliche Zusätze enthalten. Zu erwähnen sind z.B. Mineralsäuren, organische Säuren und/oder deren Salze, die der Einstellung des pH-Werts des Färbebads dienen, weiterhin Elektrolyte, Egalisier-, Netz- und Entschäumungsmittel sowie, falls es sich um das Färben von Wolle/Polyester-Gemischen handelt, Carrier und/oder Dispergiermittel.In addition to the dye, water and the wool auxiliary, the dyebath can contain other customary additives. Worth mentioning are e.g. Mineral acids, organic acids and / or their salts, which serve to adjust the pH value of the dye bath, further electrolytes, leveling agents, wetting agents and defoaming agents and, if dyeing wool / polyester mixtures, carriers and / or dispersant.
Das Färbebad weist einen pH-Wert von z.B. 4 bis 6,5 und vorzugsweise von 5,2 bis 5,8 auf. Das erfindungsgemässe Verfahren wird im allgemeinen bei einer Temperatur von z.B. 60 bis 130°C durchgeführt.The dye bath has a pH of e.g. 4 to 6.5 and preferably from 5.2 to 5.8. The process according to the invention is generally carried out at a temperature of e.g. 60 to 130 ° C carried out.
Wenn das zu färbende Material Wolle allein ist, erfolgt die Färbung zweckmässig nach dem Ausziehverfahren, z.B. bei einer Temperatur im Bereich 60 bis 106°C, vorzugsweise 95 bis 98°C. Die Färbedauer kann in Abhängigkeit von den Erfordernissen variieren, beträgt jedoch vorzugsweise 60-120 Minuten.If the material to be dyed is wool alone, the dyeing is expediently carried out using the exhaust process, e.g. at a temperature in the range 60 to 106 ° C, preferably 95 to 98 ° C. The dyeing time can vary depending on the requirements, but is preferably 60-120 minutes.
Die Färbungen der Polyester/Wolle-Mischfasermaterialien erfolgen mit Vorteil einbadig aus wässriger Flotte nach dem Ausziehverfahren. Man färbt vorzugsweise nach dem sogenannten Hochtemperaturverfahren in geschlossenen, druckbeständigen Apparaturen bei Temperaturen von über 100°C, zweckmässig zwischen 110 und 125°C und vorzugsweise bei 118-120°C und gegebenenfalls unter Druck.The dyeing of the polyester / wool mixed fiber materials is advantageously carried out in a single bath from aqueous liquor after the exhaust process. Dyeing is preferably carried out by the so-called high-temperature process in closed, pressure-resistant apparatus at temperatures above 100 ° C., expediently between 110 and 125 ° C. and preferably at 118-120 ° C. and optionally under pressure.
Die Mischfasermaterialien können auch nach dem üblichen Carrier-Färbeverfahren bei Temperaturen unter 106°C, z.B. im Temperaturbereich von 75 bis 98°C in Gegenwart eines oder mehrerer Carrier gefärbt werden.The mixed fiber materials can also be processed by the usual carrier dyeing process at temperatures below 106 ° C, e.g. in the temperature range from 75 to 98 ° C in the presence of one or more carriers.
Das Färben der Polyester/Wolle-Mischfasermaterialien kann so durchgeführt werden, dass man das Färbegut zuerst mit dem Wollschutzmittel und gegebenenfalls dem Carrier behandelt und anschliessend färbt. Man kann auch so vorgehen, dass man das Färbegut gleichzeitig mit dem Wollschutzmittel, den Farbstoffen und gegebenenfalls Hilfsmitteln behandelt. Vorzugsweise geht man mit dem Textilmischfasermaterial in eine Flotte ein, die das Wollschutzmittel und gegebenenfalls weitere übliche Hilfsmittel enthält und eine Temperatur von 40-50°C aufweist, und behandelt das Material 5 bis 15 Minuten bei dieser Temperatur. Danach erhöht man die Temperatur auf ca. 60 bis 70°C, gibt den Farbstoff zu, erhitzt langsam auf die Färbetemperatur und färbt dann ca. 20 bis 60, vorzugsweise 30 bis 45 Minuten, bei dieser Temperatur. Am Schluss wird die Flotte auf etwa 60°C abgekühlt und das gefärbte Material wie üblich aufgearbeitet.The dyeing of the polyester / wool mixed fiber materials can be carried out by first treating the material to be dyed with the wool protection agent and, if appropriate, the carrier, and then dyeing. One can also proceed in such a way that the material to be dyed is treated simultaneously with the wool preservative, the dyes and, if appropriate, auxiliaries. The textile mixed fiber material is preferably added to a liquor which contains the wool protection agent and, if appropriate, other customary auxiliaries and has a temperature of 40-50 ° C., and the material is treated at this temperature for 5 to 15 minutes. The temperature is then increased to about 60 to 70 ° C., the dye is added, the mixture is slowly heated to the dyeing temperature and then dyeing is carried out at this temperature for about 20 to 60, preferably 30 to 45 minutes. Finally, the liquor is cooled to about 60 ° C and the colored material is worked up as usual.
Mittels des erfindungsgemässen Verfahrens ist es möglich, Wolle oder insbesondere Wolle/Polyester-Fasergemische bei hoher Temperatur unter einwandfreiem Schutz des Wollanteils, d.h. unter Erhaltung der wichtigen, fasertechnologischen Eigenschaften der Wolle, wie Reissfestigkeit, Berstbeständigkeit und Dehnung, zu färben. Hervorzuheben ist weiterhin, dass der Polyesteranteil bei Mischgeweben keine Angilbung zeigt.By means of the method according to the invention it is possible to wool or in particular wool / polyester fiber mixtures at high temperature with perfect protection of the wool content, i.e. dyeing while preserving the important fiber-technological properties of the wool, such as tear resistance, bursting resistance and elongation. It should also be emphasized that the proportion of polyester in mixed fabrics shows no yellowing.
Die folgenden Beispiele veranschaulichen die Erfindung. Teile bedeuten Gewichtsteile, Prozente Gewichtsprozente.The following examples illustrate the invention. Parts mean parts by weight, percentages by weight.
In einem Sulfierkolben werden 33,2 Teile Diglycerin (0,8 OH-Aequivalente) und 2,8 g Bortrifluorid/Diessigsäure-Komplex vorgelegt und auf 75°C erwärmt. 37 Teile Epichlorhydrin werden innerhalb von ca. 2 Stunden zugetropft und dabei die Temperatur zwischen 75 und 80°C gehalten. Man lässt anschliessend noch ca. 30 Minuten bei 75°C weiterrühren, kühlt dann auf Raumtemperatur ab, neutralisiert durch Zugabe von Natriumhydroxidlösung bis pH ca. 5 und trocknet das Produkt im Vakuum.33.2 parts of diglycerol (0.8 OH equivalents) and 2.8 g of boron trifluoride / diacetic acid complex are placed in a sulfonation flask and heated to 75.degree. 37 parts of epichlorohydrin are added dropwise within about 2 hours and the temperature is kept between 75 and 80 ° C. The mixture is then left at 75 ° C. for about 30 minutes continue stirring, then cool to room temperature, neutralized by adding sodium hydroxide solution to pH approx. 5 and drying the product in vacuo.
In einem geeigneten Reaktionsgefäss werden 46 Teile Glycerin und 1 Teil Bortrifluorid-Ethyletherat unter N₂-Atmosphäre vorgelegt. 148,2 Teile Glycidol werden innerhalb von 5,5 Stunden bei 25 bis 30°C zugetropft und das Reaktionsgemisch anschliessend zunächst ca. 3 Stunden bei 50°C und dann ca. 12 bis 15 Stunden bei Raumtemperatur weitergerührt. Danach werden 92,5 Teile Epichlorhydrin innerhalb von ca. 5,5 Stunden bei 25 bis 30°C zugetropft und das Reaktionsgemisch ca. 12 Stunden bei Raumtemperatur und 3 Stunden bei 50°C weitergerührt.In a suitable reaction vessel, 46 parts of glycerol and 1 part of boron trifluoride ethyl etherate are placed under an N₂ atmosphere. 148.2 parts of glycidol are added dropwise at 5.5 to 30.degree. C. in the course of 5.5 hours, and the reaction mixture is subsequently stirred for about 3 hours at 50.degree. C. and then for about 12 to 15 hours at room temperature. 92.5 parts of epichlorohydrin are then added dropwise at about 25 to 30 ° C. over the course of about 5.5 hours, and the reaction mixture is further stirred at room temperature for about 12 hours and at 50 ° C. for 3 hours.
Zu 165,1 Teilen des oben erhaltenen Produkts werden weitere 53,3 Teile Epichlorhydrin innerhalb von ca. 3 Stunden zugetropft und dabei die Temperatur bei ca. 35 bis 40°C gehalten. Das Reaktionsgemisch wird anschliessend ca. 4 Stunden auf ca. 50°C erwärmt und dann im Vakuum getrocknet.A further 53.3 parts of epichlorohydrin are added dropwise to 165.1 parts of the product obtained above over the course of about 3 hours, the temperature being kept at about 35 to 40 ° C. The reaction mixture is then heated to about 50 ° C. for about 4 hours and then dried in vacuo.
38,8 Teile Tetraethylenglykol (0,4 OH-Aequivalente) und 2,9 Teile Bortrifluorid/Diessigsäure-Komplex werden auf 75°C erhitzt und 37 Teile Epichlorhydrin innerhalb von ca. 2 Stunden addiert. Danach lässt man ca. 30 Minuten bei 75°C weiterrühren, kühlt dann auf Raumtemperatur ab, neutralisiert bis pH 6 und trocknet das Produkt.38.8 parts of tetraethylene glycol (0.4 OH equivalents) and 2.9 parts of boron trifluoride / diacetic acid complex are heated to 75 ° C. and 37 parts of epichlorohydrin are added within about 2 hours. The mixture is then left to stir at 75 ° C. for about 30 minutes, then cooled to room temperature, neutralized to pH 6 and the product dried.
Man verfährt wie im Beispiel 3 beschrieben, setzt jedoch 41,2 Teile Polyethylenglykol 400 (0,2 OH-Aequivalente), 1,4 Teile Bortrifluorid/Diessigsäure-Komplex und 18,5 Teile Epichlorhydrin um.The procedure is as described in Example 3, but 41.2 parts of polyethylene glycol 400 (0.2 OH equivalents), 1.4 parts of boron trifluoride / diacetic acid complex and 18.5 parts of epichlorohydrin are reacted.
27,5 Teile Stärke, 15 Teile Wasser und 8,4 Teile Zn(BF₄)₂ (40%ig in Wasser) werden auf 80°C erhitzt und 64,8 Teile Epichlorhydrin innerhalb von ca. 6 Stunden bei dieser Temperatur addiert. Danach lässt man ca. 1 Stunde bei 80°C weiterrühren, fällt das Produkt in Ethanol aus und trocknet es.27.5 parts of starch, 15 parts of water and 8.4 parts of Zn (BF₄) ₂ (40% in water) are heated to 80 ° C and 64.8 parts of epichlorohydrin are added at this temperature in about 6 hours. The mixture is then left to stir at 80 ° C. for about 1 hour, the product precipitates in ethanol and dries it.
49,2 Teile Stärke, 95 Teile Dioxan und 11,4 Teile Zn(BF₄)₂ (40%ig in Wasser) werden auf 75°C erhitzt und 23,1 Teile Epichlorhydrin innerhalb von ca. 2 Stunden bei dieser Temperatur addiert. Danach lässt man ca. 2 Stunden bei 75°C weiterrühren, kühlt auf Raumtemperatur ab, filtriert das Produkt ab und trocknet es.49.2 parts of starch, 95 parts of dioxane and 11.4 parts of Zn (BF₄) ₂ (40% in water) are heated to 75 ° C. and 23.1 parts of epichlorohydrin are added at this temperature in about 2 hours. The mixture is then left to stir at 75 ° C. for about 2 hours, cooled to room temperature, the product is filtered off and dried.
Man verfährt wie im Beispiel 3 beschrieben, setzt jedoch 46,4 Teile Hydroxyethylacrylat (stabilisiert mit 0,3 Teilen Hydrochinonmonomethylether), 2,9 Teile Bortrifluorid/Diessigsäure-Komplex und 37 Teile Epichlorhydrin um.The procedure described in Example 3 is followed, except that 46.4 parts of hydroxyethyl acrylate (stabilized with 0.3 part of hydroquinone monomethyl ether), 2.9 parts of boron trifluoride / diacetic acid complex and 37 parts of epichlorohydrin are reacted.
In einem geeigneten Reaktionsgefäss werden 58 Teile Maleinsäure und 3 Teile Triethylamin vorgelegt und auf 115°C erhitzt. 74 Teile Glycidol werden innerhalb von ca. 2 Stunden zugetropft und das Reaktionsgemisch anschliessend 2 Stunden bei 115°C weitergerührt. Man kühlt auf ca. 50°C ab, gibt 4,2 Teile Bortrifluorid-Ethyletherat zu und erhitzt das Reaktionsgemisch wiederum auf ca. 115°C. Danach werden 74 Teile Glycidol innerhalb von ca. 2 Stunden zugetropft und das Reaktionsgemisch anschliessend ca. 3 Stunden weitergerührt. Zum Reaktionsgemisch werden 92,5 Teile Epichlorhydrin innerhalb von ca. 2,5 Stunden zugetropft und dabei die Temperatur bei 115°C gehalten. Das Reaktionsgemisch wird anschliessend ca. 9 Stunden bei dieser Temperatur gehalten und dann im Vakuum getrocknet.58 parts of maleic acid and 3 parts of triethylamine are placed in a suitable reaction vessel and heated to 115.degree. 74 parts of glycidol are added dropwise within about 2 hours and the reaction mixture is then stirred at 115 ° C. for 2 hours. It is cooled to about 50 ° C., 4.2 parts of boron trifluoride ethyl etherate are added, and the reaction mixture is again heated to about 115 ° C. 74 parts of glycidol are then added dropwise in the course of about 2 hours, and the reaction mixture is then stirred for a further 3 hours. 92.5 parts of epichlorohydrin are added dropwise to the reaction mixture over the course of about 2.5 hours, the temperature being kept at 115.degree. The reaction mixture is then held at this temperature for about 9 hours and then dried in vacuo.
Man setzt analog wie im Beispiel 3 beschrieben 26,8 Teile 1,1,1-Tris(hydroxymethyl)propan, 4,3 Teile Bortrifluorid/Diessigsäure-Komplex und 55,5 Teile Epichlorhydrin miteinander um.26.8 parts of 1,1,1-tris (hydroxymethyl) propane, 4.3 parts of boron trifluoride / diacetic acid complex and 55.5 parts of epichlorohydrin are reacted with one another analogously to that described in Example 3.
277,1 Teile eines Umsetzungsprodukts aus 1 Mol Pentaerythrit mit 8 Mol Glycidol werden in einem Sulfierkolben unter Stickstoffatmosphäre vorgelegt und 54,7 Teile Epichlorhydrin innerhalb von ca. 4 Stunden bei einer Temperatur von 25 bis 30°C addiert. Danach lässt man ca. 4 Stunden bei 50°C weiterrühren und trocknet dann das Produkt im Vakuum.277.1 parts of a reaction product of 1 mole of pentaerythritol with 8 moles of glycidol are placed in a sulfonation flask under a nitrogen atmosphere and 54.7 parts of epichlorohydrin are added within 4 hours at a temperature of 25 to 30 ° C. Then the mixture is left to stir at 50 ° C. for about 4 hours and the product is then dried in vacuo.
100 Teile eines Mischgewebes, bestehend aus 55 % Polyester und 45 % Wolle, werden in einem Zirkulationsapparat mit einer Flotte, die
1,5 Teile des Produkts gemäss Beispiel 1,
0,5 Teile eines sulfatierten Fettaminpolyglycolethers,
1,0 Teile eines handelsüblichen Hilfsmittelgemisches (auf Basis carbonsäure- und
phosphorsäure-aromatischer Verbindungen) und
2,0 Teile Natriumacetat
in 1200 Teilen Wasser enthält und mit Essigsäure auf pH 5,5 eingestellt ist, 5 min. bei 40°C vorbehandelt. Darauf wird die Flotte innerhalb von 30 Minuten auf 120°C erhitzt,
wobei bei 70°C 2,0 Teile der Farbstoffmischung bestehend aus
1,6 Gew.-% Farbstoff der Formel
60 Gew.-% Farbstoff der Formel
5,0 Gew.-% Farbstoff der Formel
4,0 Teile Farbstoff der Formel
3,3 Teile Farbstoff der Formel
15,0 Teile Farbstoff der Formel
und 10 Teile Natriumsulfat
der Flotte zugefügt werden. Darauf färbt man 40 min. bei 120°C und kühlt anschliessend die Färbeflotte auf 60°C ab. Darauf wird die übliche Nachwäsche durchgeführt. Man erhält eine reibechte, egale, rote Ton-in-Ton Färbung ohne Einbusse der Wollqualität.100 parts of a mixed fabric, consisting of 55% polyester and 45% wool, are in a circulation apparatus with a liquor
1.5 parts of the product according to Example 1,
0.5 parts of a sulfated fatty amine polyglycol ether,
1.0 parts of a commercially available auxiliary mixture (based on carboxylic acid and
phosphoric acid aromatic compounds) and
2.0 parts sodium acetate
contains in 1200 parts of water and is adjusted to pH 5.5 with acetic acid, 5 min. at Pretreated at 40 ° C. The liquor is then heated to 120 ° C within 30 minutes,
whereby at 70 ° C 2.0 parts of the dye mixture consisting of
1.6% by weight of dye of the formula
60% by weight of dye of the formula
5.0% by weight of dye of the formula
4.0 parts of dye of the formula
3.3 parts of dye of the formula
15.0 parts of dye of the formula
and 10 parts of sodium sulfate
be added to the fleet. It is stained for 40 min. at 120 ° C and then cools the dye liquor to 60 ° C. The usual post-wash is then carried out. You get a rub-fast, level, red tone-on-tone coloring without loss of wool quality.
Verwendet man anstelle der wässrigen Zubereitung gemäss Beispiel 1
- (a) 1,3 Teile des Produkts gemäss Beispiel 2,
- (b) 1,4 Teile des Produkts gemäss Beispiel 3,
- (c) 1,4 Teile des Produkts gemäss Beispiel 4,
- (d) 1,6 Teile des Produkts gemäss Beispiel 5,
- (e) 1,4 Teile des Produkts gemäss Beispiel 6,
- (f) 1,3 Teile des Produkts gemäss Beispiel 7,
- (g) 1,3 Teile des Produkts gemäss Beispiel 8,
- (h) 1,8 Teile des Produkts gemäss Beispiel 9,
- (i) 1,4 Teile des Produkts gemäss Beispiel 10,
so erhält man ebenfalls Färbungen mit guten Eigenschaften und ohne negative Beeinflussung der Wollqualität.Is used instead of the aqueous preparation according to Example 1
- (a) 1.3 parts of the product according to Example 2,
- (b) 1.4 parts of the product according to Example 3,
- (c) 1.4 parts of the product according to Example 4,
- (d) 1.6 parts of the product according to Example 5,
- (e) 1.4 parts of the product according to Example 6,
- (f) 1.3 parts of the product according to Example 7,
- (g) 1.3 parts of the product according to Example 8,
- (h) 1.8 parts of the product according to Example 9,
- (i) 1.4 parts of the product according to Example 10,
this also gives dyeings with good properties and without adversely affecting the quality of the wool.
100 Teile eines Wollgewebes mit einem m²-Gewicht von 180 g werden in 1000 Teilen einer wässrigen Flotte enthaltend 4 Teile Ammoniumsulfat, 1,5 Teile des Produkts gemäss Beispiel 1 und 0,5 Teile eines Naphthalinsulfonsäure-Kondensatprodukts 10 min bei 50°C behandelt; der pH-Wert der Flotte wird zuvor mit Essigsäure auf ca. 6 eingestellt. Danach werden 3 Teile des Farbstoffs der Formel
zugesetzt und weitere 5 min. behandelt. Anschliessend wird die Färbeflotte innerhalb von ca. 45 min. auf ca. 98°C erhitzt und das Gewebe 60 min. bei dieser Temperatur gefärbt.100 parts of a wool fabric with a m² weight of 180 g are treated in 1000 parts of an aqueous liquor containing 4 parts of ammonium sulfate, 1.5 parts of the product according to Example 1 and 0.5 part of a naphthalenesulfonic acid condensate product for 10 minutes at 50 ° C .; the pH of the liquor is previously adjusted to about 6 with acetic acid. Then 3 parts of the dye of the formula
added and a further 5 min. treated. The dyeing liquor is then removed within approx. 45 min. heated to approx. 98 ° C and the tissue for 60 min. colored at this temperature.
Danach lässt man auf ca. 60°C abkühlen, spült wie üblich und trocknet das gefärbte Gewebe. Man erhält eine reibechte, egale Blaufärbung ohne negative Beeinflussung der Wollqualität.Then allow to cool to approx. 60 ° C, rinse as usual and dry the dyed fabric. You get a rub-fast, level blue color without negatively influencing the wool quality.
Verwendet man anstelle der wässrigen Zubereitung gemäss Beispiel 1
- (a) 1,3 Teile des Produkts gemäss Beispiel 2,
- (b) 1,4 Teile des Produkts gemäss Beispiel 3,
- (c) 1,4 Teile des Produkts gemäss Beispiel 4,
- (d) 1,6 Teile des Produkts gemäss Beispiel 5,
- (e) 1,4 Teile des Produkts gemäss Beispiel 6,
- (f) 1,3 Teile des Produkts gemäss Beispiel 7,
- (g) 1,3 Teile des Produkts gemäss Beispiel 8,
- (h) 1,8 Teile des Produkts gemäss Beispiel 9,
- (i) 1,4 Teile des Produkts gemäss Beispiel 10,
so erhält man ebenfalls Färbungen mit guten Eigenschaften und ohne negative Beeinflussung der Wollqualität.Is used instead of the aqueous preparation according to Example 1
- (a) 1.3 parts of the product according to Example 2,
- (b) 1.4 parts of the product according to Example 3,
- (c) 1.4 parts of the product according to Example 4,
- (d) 1.6 parts of the product according to Example 5,
- (e) 1.4 parts of the product according to Example 6,
- (f) 1.3 parts of the product according to Example 7,
- (g) 1.3 parts of the product according to Example 8,
- (h) 1.8 parts of the product according to Example 9,
- (i) 1.4 parts of the product according to Example 10,
this also gives dyeings with good properties and without adversely affecting the quality of the wool.
Je 10 Teile eines Wollgewebes und 10 Teile eines gebleichten Polyestergewebes werden zusammen in 200 Teilen einer mit Essigsäure auf pH 5,5 eingestellten Flotte enthaltend 0,6 Teile des Produkts gemäss Beispiel 1 und 0,4 Teile Natriumacetat 5 min. bei 40°C vorbehandelt. Darauf erhitzt man die Flotte innerhalb von 30 min. auf 120°C, behandelt das Gewebe 40 min. bei dieser Temperatur und kühlt anschliessend auf 60°C ab. Nach der so durchgeführten Blindbadbehandlung (ohne Farbstoff) zeigt das Wollgewebe keine Qualitätseinbussen z.B. bezüglich der Berstbeständigkeit; ebenso zeigt das Polyester-Begleitgewebe keine Angilbung durch den hydrolytischen Abbau der Wolle.10 parts of a wool fabric and 10 parts of a bleached polyester fabric are combined in 200 parts of a liquor adjusted to pH 5.5 with acetic acid containing 0.6 part of the product according to Example 1 and 0.4 part of sodium acetate for 5 minutes. pretreated at 40 ° C. The liquor is then heated within 30 minutes. to 120 ° C, the fabric is treated for 40 min. at this temperature and then cools down to 60 ° C. After the blind bath treatment (without dye) carried out in this way, the wool fabric shows no loss of quality, e.g. in terms of burst resistance; the polyester accompanying fabric also shows no yellowing due to the hydrolytic degradation of the wool.
Aehnlich gute Effekte bezüglich der Berstbeständigkeit der Wolle und dem Nicht-Angilben des Polyester-Gewebes werden erzielt, wenn man anstelle des Produkts gemäss Beispiel 1
- (a) 0,55 Teile des Produkts gemäss Beispiel 2,
- (b) 0,60 Teile des Produkts gemäss Beispiel 3,
- (c) 0,60 Teile des Produkts gemäss Beispiel 4,
- (d) 0,65 Teile des Produkts gemäss Beispiel 5,
- (e) 0,60 Teile des Produkts gemäss Beispiel 6,
- (f) 0,55 Teile des Produkts gemäss Beispiel 7,
- (g) 0,55 Teile des Produkts gemäss Beispiel 8,
- (h) 0,75 Teile des Produkts gemäss Beispiel 9,
- (i) 0,55 Teile des Produkts gemäss Beispiel 10
verwendet.Similar good effects with regard to the bursting resistance of the wool and the non-yellowing of the polyester fabric are achieved if instead of the product according to Example 1
- (a) 0.55 part of the product according to Example 2,
- (b) 0.60 parts of the product according to Example 3,
- (c) 0.60 parts of the product according to Example 4,
- (d) 0.65 part of the product according to Example 5,
- (e) 0.60 parts of the product according to Example 6,
- (f) 0.55 part of the product according to Example 7,
- (g) 0.55 part of the product according to Example 8,
- (h) 0.75 parts of the product according to Example 9,
- (i) 0.55 parts of the product according to Example 10
used.
Claims (13)
R - O - CH₂ - CH(OH) - CH₂- Y (1),
worin Y Halogen bedeutet und R
R - O - CH₂ - CH (OH) - CH₂- Y (1),
where Y is halogen and R
- O - CH₂ - CH(OH) - CH₂ - Y (2),
- O - (CH₂CH₂O)x - H (3)
-O-(CH₂CH[CH₃]O)y - H (4)
oder
- O - (CH₂CH[OH]CH₂O)z - H (5),
worin Y Halogen und x, y und z unabhängig voneinander je eine Zahl von 1 bis 200 bedeuten, vorliegen.A method according to claim 1 or 2, characterized in that the radical R has one or more hydroxy groups and this partially or completely in the form of a radical of the formula
- O - CH₂ - CH (OH) - CH₂ - Y (2),
- O - (CH₂CH₂O) x - H (3)
-O- (CH₂CH [CH₃] O) y - H (4)
or
- O - (CH₂CH [OH] CH₂O) z - H (5),
where Y is halogen and x, y and z each independently represent a number from 1 to 200.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH228293 | 1993-07-28 | ||
| CH228293 | 1993-07-28 | ||
| CH2282/93 | 1993-07-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0636743A2 true EP0636743A2 (en) | 1995-02-01 |
| EP0636743A3 EP0636743A3 (en) | 1998-04-22 |
| EP0636743B1 EP0636743B1 (en) | 1999-12-29 |
Family
ID=4230131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94810425A Expired - Lifetime EP0636743B1 (en) | 1993-07-28 | 1994-07-19 | Process for dyeing of wool-containing fibre materials |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5460630A (en) |
| EP (1) | EP0636743B1 (en) |
| DE (1) | DE59409028D1 (en) |
| ES (1) | ES2141211T3 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19519021A1 (en) * | 1995-05-24 | 1996-11-28 | Hoechst Ag | Polysaccharide dye formulation |
| DE19533713C1 (en) * | 1995-09-12 | 1997-01-23 | Boehme Chem Fab Kg | Agent protecting wool in high temp. wet treatment, causing little discoloration |
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|---|---|---|---|---|
| US5948125A (en) * | 1997-05-20 | 1999-09-07 | Ciba Specialty Chemicals Corporation | Method of treating dyed, natural or synthetic polyamide fibre materials |
| US7815900B1 (en) * | 2000-07-11 | 2010-10-19 | L'ORéAL S.A. | Use of C3-C5 monosaccharides to protect keratinous fibers |
| US7776108B2 (en) * | 2005-06-07 | 2010-08-17 | S.C. Johnson & Son, Inc. | Composition for application to a surface |
| CA2610962C (en) * | 2005-06-07 | 2012-08-28 | S. C. Johnson & Son, Inc. | Method of applying a design to a surface |
| US8557758B2 (en) | 2005-06-07 | 2013-10-15 | S.C. Johnson & Son, Inc. | Devices for applying a colorant to a surface |
| US8846154B2 (en) * | 2005-06-07 | 2014-09-30 | S.C. Johnson & Son, Inc. | Carpet décor and setting solution compositions |
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| EP0582550A1 (en) * | 1992-08-06 | 1994-02-09 | Ciba-Geigy Ag | Process for dyeing of wool-containing fibrous materials |
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| DE59104446D1 (en) * | 1990-02-14 | 1995-03-16 | Ciba Geigy Ag | Process for dyeing wool with reactive dyes. |
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1994
- 1994-07-19 EP EP94810425A patent/EP0636743B1/en not_active Expired - Lifetime
- 1994-07-19 DE DE59409028T patent/DE59409028D1/en not_active Expired - Fee Related
- 1994-07-19 ES ES94810425T patent/ES2141211T3/en not_active Expired - Lifetime
- 1994-07-21 US US08/278,596 patent/US5460630A/en not_active Expired - Fee Related
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| FR1565248A (en) * | 1967-05-13 | 1969-04-25 | ||
| EP0582550A1 (en) * | 1992-08-06 | 1994-02-09 | Ciba-Geigy Ag | Process for dyeing of wool-containing fibrous materials |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19519021A1 (en) * | 1995-05-24 | 1996-11-28 | Hoechst Ag | Polysaccharide dye formulation |
| DE19519021C2 (en) * | 1995-05-24 | 1998-09-03 | Dystar Textilfarben Gmbh & Co | Polysaccharide dye formulation |
| DE19533713C1 (en) * | 1995-09-12 | 1997-01-23 | Boehme Chem Fab Kg | Agent protecting wool in high temp. wet treatment, causing little discoloration |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59409028D1 (en) | 2000-02-03 |
| US5460630A (en) | 1995-10-24 |
| ES2141211T3 (en) | 2000-03-16 |
| EP0636743A3 (en) | 1998-04-22 |
| EP0636743B1 (en) | 1999-12-29 |
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