IL35610A - Process for the finishing of textiles - Google Patents
Process for the finishing of textilesInfo
- Publication number
- IL35610A IL35610A IL35610A IL3561070A IL35610A IL 35610 A IL35610 A IL 35610A IL 35610 A IL35610 A IL 35610A IL 3561070 A IL3561070 A IL 3561070A IL 35610 A IL35610 A IL 35610A
- Authority
- IL
- Israel
- Prior art keywords
- epoxide
- acid
- groups
- reaction product
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- 239000004753 textile Substances 0.000 title claims description 19
- 150000002924 oxiranes Chemical class 0.000 claims description 61
- 239000007795 chemical reaction product Substances 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 32
- -1 alicyclic hydro-carbons Chemical class 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 21
- 239000004952 Polyamide Substances 0.000 claims description 19
- 229920002647 polyamide Polymers 0.000 claims description 19
- 210000002268 wool Anatomy 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 15
- 238000009950 felting Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 229920003180 amino resin Polymers 0.000 claims description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000005011 alkyl ether group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 238000009877 rendering Methods 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims 1
- 150000008040 ionic compounds Chemical class 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 238000004519 manufacturing process Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 235000020778 linoleic acid Nutrition 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229960004488 linolenic acid Drugs 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-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
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 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
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229960002415 trichloroethylene Drugs 0.000 description 2
- 229960001124 trientine Drugs 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
- RWNLZGABRBZBGD-UHFFFAOYSA-N (triazin-4-ylamino)methanol Chemical class OCNC1=CC=NN=N1 RWNLZGABRBZBGD-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- UWJSEKIPBCUKSY-UHFFFAOYSA-N 1,1,2,2-tetrachloroethene;1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl.ClC(Cl)=C(Cl)Cl UWJSEKIPBCUKSY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RJPLHMDZINIJFR-UHFFFAOYSA-N 1-[2-(1-hydroxycyclohexa-2,4-dien-1-yl)propan-2-yl]cyclohexa-2,4-dien-1-ol Chemical compound C1C=CC=CC1(O)C(C)(C)C1(O)CC=CC=C1 RJPLHMDZINIJFR-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
- PIFPCDRPHCQLSJ-WYIJOVFWSA-N 4,8,12,15,19-Docosapentaenoic acid Chemical compound CC\C=C\CC\C=C\C\C=C\CC\C=C\CC\C=C\CCC(O)=O PIFPCDRPHCQLSJ-WYIJOVFWSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical class CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KYXHKHDZJSDWEF-LHLOQNFPSA-N CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 Chemical compound CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 KYXHKHDZJSDWEF-LHLOQNFPSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PIFPCDRPHCQLSJ-UHFFFAOYSA-N Clupanodonic acid Natural products CCC=CCCC=CCC=CCCC=CCCC=CCCC(O)=O PIFPCDRPHCQLSJ-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Polymers S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- ZKCRKOCVERWCLP-DJWHJZFYSA-N Hiragonic acid Chemical compound C\C=C\CC\C=C\CC\C=C\CCCCC(O)=O ZKCRKOCVERWCLP-DJWHJZFYSA-N 0.000 description 1
- ZKCRKOCVERWCLP-UHFFFAOYSA-N Hiragonic acid Natural products CC=CCCC=CCCC=CCCCCC(O)=O ZKCRKOCVERWCLP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000005521 carbonamide group Polymers 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021290 n-3 DPA Nutrition 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Process for the finishing
of textiles
CIBA-GBIGY AO
•The subject of the 'invention is a process for the finishing of textiles, especially for rendering wool non-felting, characterised in that the textiles are treated with a preparation which (1) in a water-insoluble organic solvent, contains (2) a reaction product of a)a' ) a basic polyaniide and a") an epoxide, an alkyl ether of an aminoplast pre-condensate or an epoxide-polyraeri c unsaturated fatty acid reaction product, or b)b') an epoxide-organic carboxylic acid reaction product and b") an amine, or .amino-epoxide reaction product and (3) a surface-active dispersing agent which is soluble in organic solvents, that the solvent is subsequently removed from the textiles thus treated, and that thereafter the textiles, if .desired/ are subjected to an after-treatment at room temperature ...of at elevated temperature.
Preferably, the exhaustion process is here used. As a rule it suffices if the preparation for the non-felting treatment is allowed to act on the textiles for 15 to 60 minutes at a temperature of 20 to 80°C, preferably 30 to 50°C. An addition of a low molecular aliphatic carboxylic acid, such as for example formic acid or acetic acid, to the treatment bath at a concentration of up to 20 ml/litre has proved -useful in many cases, especially in the case of a combined application together with optical brighteners. It is advantageous if, subsequent to this treatment and after the solvent have been removed from the treated textiles, for example by centrifuging, the textiles are subjected to an after-treatment for example by storing at room temperature for 2 to 10 days : or to a heat treatment at preferably 40 to 200°C, especiall 80°C, for 60 to 15 minutes, especially 60 minutes.
If desired, the preparation which is used for the
finishing can contain yet further additives, such as for example other textile finishing agents, for example optical "brighteners or agents for imparting a soft handle.
The wool to be finished can be in any desired state of processing, for example in the form of slubbing, -yarn or garments, such as pullovers.
Further, it is also possible to use a combined process for dyeing wool and rendering it non-felting, in which, simultaneously or subsequently in optional sequence, using the exhaustion method, the wool is on the one hand dyed and on the other hand treated with the preparations according to the invention. Dyeing and rendering non-felting can thereby in a simple manner be combined and carried out in the same apparatus, v/ithout the wool being taken out of the apparatus between the two processes.
Dyeing can here be carried out in the usual manner which is in itself known, using any desired dyes tuffs which can be used for wool. Equally, the additives which are customary in dyeing wool can be employed, such as levelling agents, for example polyglycol compounds of higher aliphatic amines .
The amount of the reaction product (2) (not ' including solvent), relative to the weight of the wool, is appropriately 0.5 to 5 i», preferably 1.2 to 31°.
The sequence of the two processes is optional/ but in general it tends to be advantageous to carry out dyeing first and the non-felting treatment subsequently, though it is also possible to carry out dyeing and the non-feltin treatment simultaneously using the same bath..
water-inso.luble solvents can be used for carrying out the present process, that is to say solvents which at 20°C only take up very snail amounts of water, for example 0.01 to 1 $ by weight. The
are for example suitable: petrol . hydrocarbons, such as petrol ether; benzene and halogenated benzenes or benzenes substituted by lower alkyl groups, such as toluene, ethylbenzene , cumene or xylene; alicyclic hydrocarbons such as tetralin or cyclohexane; or, especially, halogenated aliphatic hydrocarbons. Preferred halogenated aliphatic hydrocarbons are above all the solvents used in the dry cleaning industry, such as methylene chloride, methylene bromide, chloroform, carbon tetrachloride, ethylene chloride, ethylene bromide, 1 , 1 , 1 -trichloroethane, s-tetrachloroethane or especially trichlor oethylene and perchloroethylene . .
Mixtures of the solvents mentioned can also be used.
As component (2), a reaction product of a)a') a basic polyamide from polymeric, unsaturated fatty acids and poly-alkylenepolyamines , and a") an epoxide or an aminoplast · precondensate containing alkyl ether groups, or b)b') a reaction product of an epoxide, which per molecule contains at least 2 epoxide groups, and an organic carboxylic . acid , which per molecule contains at least 2 carboxyl groups, and b") an amine containing at least two amino groups or a reaction product of an amine containing at least 2 amino groups per molecule with an epoxide containing at least 2 epoxide groups per molecule, is preferably used.
The reaction products used as component (2) are especially one of the following 3 types:
1, Reaction products of epoxides and amino compounds, which are obtained by reacting epoxides' in an equivalent.
, * 35610/2
ratio of 1 : 1 to 1 : 5 with basic polyamides from polymeric, preferably dimeric to triraeric, unsaturated fatty acids and polyalkylenepolyamines in the presence of organic' solvents at temperatures of at most 80°C, to give pblyaddition com-pounds which are soluble or dispersible in water, and ensuring, through the' addition of acid, not later than on completion of the reaction, that a* sample of the reaction, mixture has a pH-value of 2 to 8 after addition of water.
2. Reaction products of aminoplast precondensates. and amino compounds, which are obtained by reacting aminoplast precondensates containing alkyl-ether groups, in. the.
presence of organic solvents, with basic polyamides from polymeric, preferably dimeric, unsaturated fatty acids and poly- i
alkylenepolyamines to give water-soluble compounds, and :
ensuring, through. the addition of acid, not later than
immediately on completion of the reaction, that a sample of . the reaction mixture has a pH-value of 2 to 8, preferably .2 _ to 7» after addition of water. · ■■!.·'
3 Reaction produc s of epoxides and amines, which are obtained by reacting b) b') a reaction product of at leas
one epoxide which contains at least two epoxide groups per
molecule, and at least one organic carboxylic acid, which con* tains at least 2 carboxyl groups per molecule, with the
equivalent ratio of epoxide groups to acid groups being
0.1 to 1 : 0.8, with b" ) an amine containing at least two amino groups, wherein the amino groups each possess at least one
hydrogen atom bonded to nitrogen, or a reaction product of
said amine with an epoxide, which per molecule contains at least two epoxide groups and wherein the equivalent ratio of hydrogen,
epoxide groups 'is 3 : t to 11 : 1, in the presence of an
organic solvent, the equivalent ratio of epoxide groups to
hydrogen bonded to amine nitrogen being 1 : 2 to 1 : 10, and
ensuring, through addition of acid, not later than on completion of the reaction, that a sample of the reaction mixture has a pH-value of 2 to 8 after dilution with water.
The epoxides which are used for the manufacture of
the reaction products of type 1 and 3 to be used according
to the invention are as a rule liquid at room temperature,
that is to say at 15 to 25°C, and are preferably derived from polyhydric phenols or polyphenols, such as resorcinol, phenol- formaldehyde condensation products of the type of the resols, or novolacs. Bisphenols, such as bis-(4-hydroxyphenyl)- methane and above. all 2,2-bis-( 1 -hydroxyphenyl) -propane , are especially preferred as starting compounds for the manufacture of the epoxides.
Epoxides of 2, 2-bis-( 4' -hydroxyphenyl )-propane, which have an epoxide content of 3.8 to 5.8 epoxide group equivalents/kg, but preferably at least 5 epoxide group equivalents/
wherein z denotes an average number having a value of 0' to
0.65, ma here be particularly mentioned. Such epoxides are
obtained by reacting epichlorohydrin with 2 , 2-bis-(4 ' -hydroxy-phenyl ) -propane .
Suitable polymeric unsaturated fatty acids for the manufacture of the basic polyamides , which ih turn are used for the manufacture of reaction products of type 1 and 2 to be used according to the invention, are above all aliphatic, ethylenically unsaturated dimeric to trimeric fatty acids.
Preferably, aliphatic unsaturated dimeric to trimeric fatty acids which are derived from monocarboxylic acids with 16 to 22 carbon atoms,, are used. These monocarboxylic acids are fatty acids with at least one, preferably 2 to'5, ethylenically unsaturated bonds. Representatives of this class of acids are, for example, oleic acid, hiragonic acid, eleostearic acid,- ~ licar.ic acid, arachidonic acid , clupanodonic acid and especially linoleic acid and linolenic acid. These fatty acids can be obtained from natural oils, wherein they occur above all as glycerides.
The dimeric to trimeric fatty acids used according to the invention are obtained in a known manner by dimerisation of monocarboxylic acids of the indicated nature. The so-called .dimeric fatty acids always contain some trimeric acids and a small amount of monomeric acids.
Particularly suitable fatty acids are dimerised to trimerised linoleic acid or linolenic acid. The technical products of these acids as a rule contain 75 to 95 by
weight of dimeric acid, 4 to 25 per cent by weight of trimeric acid and from a trace to 3% of monomeric acid.. The molar ratio of dimeric to trimeric acid is accordingly about 5 : 1 to
these polymeric fatty acids, especially of the dimerised to trimerised linoleic or linolenic acid, with polyamines, especially aliphatic polyamines such as diethylenetriamine, trie thylenetetramine and tetraethylenepentarnine , that is to say amines of formula
(2) H2N-(CH2-CH2-NH)n-CH2-CH2- H2 - wherein n is equal to 1 , 2 or 3 and can, in the case of mixtures, also assume a non-integral average value, for example between 1 and 2. These polyamides must be basic, and this is achieved by employing an excess of amino groups
(Hg - and , alkylene-NH-alkylene ) in comparison to the
carboxylic acid groups during the polyamide condensation.
The aminoplast precondensat es which serve as starting substances for the manufacture of the reaction products of type 2 are completely, or especially partially, etheri-fied methylol compounds of nitrogen-containing substances which form amnoplastics , such as urea and urea derivatives, for example ethyleneurea , propyleneurea and glyoxalmonourein.
Preferably, etherified methylolaminotriazines are employed, such as for example alkyl ethers of highly methylol-ated melamine , of which the alkyl radicals contain 1 to 4 carbon atoms. Possible alkyl radicals are, amongst others, methyl, ethyl, n-propyl, isopropyl, n-butyl and n-hexyl radicals. In addition to such alkyl radicals, further radicals,, for example polyglycol radicals, can also be present in the molecule. Furthermore, n-butyl ethers of a highly methylo ated melamine, containing 2 to 3 butyl groups in the molecule, are preferred. By highl methylolated mela ines there are
here to be understood those with an average of at least 5, and appropriately about 5.5, methylol groups.
Suitable organic- carboxylic acids, with at least 2 carboxyl groups "per molecule, for the manufacture of the reaction products of type 3 are above all aliphatic,:
ethylenically unsaturated,, dimeric to trimeric fatty acids, such as are used for the manufacture of the basic polyamides. In addition it is also possible to use aliphatic dicarboxylic acids v/ith 2 to 10, preferably 4 to 10, carbon atoms, or aromatic, preferably monocyclic aromatic, dicarboxylic acids.
As aliphatic dicarboxylic acids, alkylenedicarboxylic acids with 4 to 10 carbon atoms are above all of interest, such as for example succinic acid, adipic acid , azaleic acid or sebacic acid. Further possible aliphatic dicarboxylic acids are also oxalic acid, fumaric acid or maleic acid.
Preferred aromatic dicarboxylic acids are benzenedicarboxylic acids, such as phthalic acid or terephthalic acid.
Dicarboxylic acids such as maleic acid or phthalic acid are preferably reacted as the acid anhydrides with the epoxide .
The diamines to be used in the manufacture of the reaction products of type 3 can be aliphatic, cyclo'aliphatic , heterocyclic or aromatic and preferably possess at least one primary amino group and a second amino group wherein at . least one hydrogen atom is bonded to nitrogen. Particularly suitable heterocyclic or aromatic amines are, for example,
piperazines, such as N ,1T · -bis-( 3-amino-propyl )-piperazine , or phenylamines , such as bis-( 3-methyl-4-aminophenyl )-methane . However, di-primary aliphatic or cycloaliphatic amines are preferred .
Suitable aliphatic amines are here' above all poly-amines, such as have been described for the manufacture of the basic polyamides.
Suitable cycloalip'hatic amines are above all di-primary, cycloaliphatic diamines, which apart from the two amine nitrogen atoms only contain carbon and hydrogen and which possess a saturated 5-membered to 6-membered carbocycli ring, an HgN group bonded to a ring carbon atom, and an
HgN-CHg- group bonded to another ring carbon atom.
As examples of such amines, 3 > , 5-trimethyl-1 -amino-3-aminomethyl-cyclohexane or 1 -amino-2-aminomethyl-cyclo-pentane may be mentioned.
The amine can now be employed by itself. or as a reaction product with an epoxide, for the manufacture of reaction products of type 3. Here, the same epoxides can be used as are employed for the manufacture of the reaction products with the organic carboxylic acids or of the reaction products of type 1, Since the equivalent ratio of amino groups to epoxide groups in component b" ) is 3 to 5.5 to 1, the amino groups are always present in excess, and epoxide groups can no longer be detected in the amine-epoxide
reaction product b"). The epoxides used for the manufacture of the component b" ) therefore do not influence the equiva- · lent ratio of epoxide groups to hydrogen, 'bonded to amine nitrogen, of 1 : 2 to 1 : 10 in the end product from components a) and b).
In the manufacture of the reaction products of type 1 the epoxides. are reacted with the basic polyamides in the equivalent ratio of 1 : 1 to■.1 : 5. By one epoxide group e uivalent there is to be understood the amount of e oxide
in grams, which is equivalent to one mol of monoepoxy compound, and by one amino group equivalent there is to be understood the amount of basic polyamide equivalent to one mol of monoamine. The equivalent values can be determined in a known manner.
The' polyaddition products of epoxides and polyamides can also be obtained, if desired, with the conjoint use o "a third component, namely a monofunct ional compound. These monofunct ional compounds possess a mobile halogen atom or a vinyl, acid, ester, acid anhydride, isocyanate or epoxide group as functional groups or atoms.
The aminoplast precondensates are reacted with the basic' polyamides in the equivalent ratio of 1 : 0,11 to
1 : 1.45 when manufacturing the reaction products of type 2. In the case of the aminoplast precondensates, an equivalent is to be understood as- the quotient of the molecular weight and the total number of methylol groups (free plus etherified) present in the molecule. The amount of basic polyamide equivalent to one mol of monoamine corresponds to one amino equivalent. Thus, for example, one mol of methylol compound containing an average of 5.5 (partially etherified) methylol groups is reacted with the amount of basic polyamide corresponding to 0.6 to 8 amino equivalent values.
When manufacturing the reaction pro ducts of type 3> yet a third component a'") can optionally be used conjointly. This component a"') is an alcohol possessing at least two hydro xyl groups. Aliphatic dihydroxy compounds, such as ethylene glycol, diethylene glycol or alkylenediols , for example 1 ,4-butanediol , are preferred.
The reaction roducts .to be used accordin to the
invention are manufactured in the presence of organic
solvents.
Suitable organic solvents are here primarily water-soluble organic solvents .
Dioxane, isopropanol, ethanpl and methanol, ethylene glycol-n-butyl ether (= n-butylglycol) and diethylene glycol-monobutyl ether may be mentioned as examples.
At the same time it is however, also possible to carry out the reaction in the presence of water-insoluble organic solvents, the same solvents as those from which the application to the textiles is subsequently effected.
As surface-active agents fqr the manufacture of the preparation of the reaction products, to be used according to the invention, anionic or non-ionic surface-active compounds are advantageously used, it being necessary to ensure tha these possess good solubility in the organic solvents which are used for the finishing process , Addition products of ethylene oxide to long-chain amines, alcohols, phenols or fatty acid esters are above all of special interest,
Suitable representatives of surface-active compounds furthermore belong to the following types of compound:
a) Ethers of polyhydroxy compounds, such as polyoxalkyl-ated fatty alcohols, polyoxalkylated polyols , polyoxalkylated mercaptans and aliphatic amines, polyoxalkylated alkylphenols and alkylnaphthols, polyoxalkylated alkylarylmercaptans and alkylarylamines ; · further, the corresponding esters of these compounds with polybasic acids, such as sulphuric acid or phosphoric acid, optionally also in the form of ammonium salts or amine salts.
b Fatt acid esters of the eth lene and ol eth lene
Γ
glycols, as well as of propylene and butylene glycol, of glycerine or of the polyglycerine s and of pentaerythritol , and also of sugar alcohols, such as sorbitol,
c) N-Hydroxyalkyl-carbonamides , polyoxalkylated carbon- amides and sulphonamide3.
As advantageously usable dispersing agents from these groups, there may for example be mentioned: the monoethanol- amine salt of the phosphoric acid ester of the addition
product of oleyl alcohol and 6 mols of ethylene oxide; the ammonium salt of the acid, sulphuric acid ester of the addition product of M mols of ethylene oxide to oleyl alcohol, and the addition product of 4 mols of ethylene oxide, to nonyl- phenol; the addition product of 8 mols of ethylene oxide to 1 mol of p-tert ,-octylphenol, of 15 or 6 mols of ethylene oxide to castor oil, and of 20 mols of ethylene oxide to the alcohol CjgH-j^OH, the ethylene oxide addition product to di-[o-phenylethyl ]-phenols , polyethylene oxide-tert ,-dodecyl- thioethers, polyamine-polyglycol-ethers , addition products of 15 or 30 mols of ethylene oxide to 1 mol of amine Cj 2^25^ 2 or. oleic acid trie.thylene glycol esters, oleic
acid-polyethylene glycol 200-esters, oleic acid-polyethylene glycol 400-esters, the adducts of 1 mol of oleic acid to 4 or 5 mols of ethylene oxide, and the adduct of 4 mols of ethylene' oxide to 1 mol of oleic acid sorbitane ester and sorbitahe monolaurate, sorbitane onopalmitate and sorbitane mono- stearate .
Mixtures of the surface-active compounds mentioned are also suitable
The preparations to be used according to the invention are appropriately prepared by stirring the reaction products
into the water-insoluble organic solvent in the presence of the dispersing agent. As a rule the reaction product, which is preferably obtained as an organic solution when manufactured, is dissolved or diluted, before being dispersed, by means of a polar solvent such as a lower alkanol, for example ethanol or especially methanol. Stable dispersions are thereby always obtained. The initially mentioned addition of low molecular carboxylic acids to the treatment bath is preferably made before the addition of the reaction product.
A further possibility consists of first working the ■ reaction product into a dough with the surface-active agent and then to introduce this into the water-insoluble solvent, whilst stirring.
Good and durable non-felting effects are thus obtained on the treated textiles by means of the process according .to the invention. The process has the advantage that it is carried out in the weakly acid to neutral range and not. in ' the alkaline range.
A further advantage in the process according to the invention is based on the fact that it is possible to work by the exhaustion process, which gives a much more uniform finish than when working with non-substantive products by the "dip roller" or spray process.
In the manufacturing instructions and examples which follow, percentages are percentages by weight.
Manufacturing Instructions
A. 98.8 g of a polyamide from polymeri sed linoleic acid and diethylenetriamine, with an amine equivalent weight of
247, are dissolved in 53 g of n-butylglycol , and the solution warmed to 50°C internal temperature. A solution of 19,1 g
of an epoxide formed from 2 ,2-bis-(4* -hydroxy-phenyl) -propane and epichlorohjdrin havin an epoxide equivalent weight of 191, in 53 g of n-butylglycol, is then added dropwise over the course of 30 minutes. 45 minutes thereafter, a sample gives a clear solution in glacial acetic acid/water (2 : 19). 15 g of glacial acetic acid and 33 g of perchloroethylene are now added and the mixture is further stirred until cold, A mobile solution of 20 $ solids content is obtained.
B. 49.4 g of a polyamide according to Instruction A, together with 67.6 g of an 80 °/o strength solution of a hexa-methylolmelamine-dibutyl ether and hexame thylolmelamine-tributyl ether in n.-butanol, are dissolved in 94 g of n-butylglycol, and the solution is warmed to 80°C internal temperature. 8 hours thereafter, a sample gives an opalescent
solution in glacial acetic acid/ water . (1 : 10), 12 g of glacial acetic acid, 82 g of n-butylglycol and 200 g of perchloroethylene are now added and the mixture is further stirred until cold. A clear solution of medium viscosity and of 20 $ solids content is obtained,
C . 110 g of an epoxide according to Instruction A
(0.576 epoxide group equivalent) together with 88 g of polymerised linoleic acid (0.314 acid group equivalent) are warmed for 2 hours to 150°C internal temperature, whilst stirring.
A highly viscous, clear product with an epoxide group equivalent weight of 758 and an acid number of 3 is obtained. 91.1 g of this epoxide are dissolved in 90 g of n-butylglycol and the solution warmed to 54°C internal temperature. A solution of 14.6 g of triethylenetetramine in 15 g of n-butylglycol is then added dropwise over the course of 40 minutes. 20
acetic acid/water (1 : 10) . 18 g of glacial acetic acid,
87 g of butylglycol and 200 g of perohloroethylene are now added, and the mixture is further stirred until cold, .A mobile, clear solution of 20 ft solids content is obtained.
Dj_ a) 95.5 g of an epoxide formed from 2, 2-bis-(4 ' -hydroxy- · phenyl ) -propane and epichlorohydrin (= 0.5 epoxide equivalent) together with 14.6 g of adipic acid (0.2 acid equivalent) are warmed for 2 hours to 150°C internal temperature, A highly viscous, clear product with an epoxide equivalent weight of 472 and an acid number of 0 is obtained.
b) 173.6 g (= 1.02 mol) of 1 -amino-3-aminomethyl-3> > 5-trimethyl-cyclohexane are initially introduced into a
stirred vessel and warmed at 100°C, under nitrogen, 76.4 g of an epoxide formed from 2 , 2-bis-( ' -hydroxyphenyl )-propane and epichlcrohydrin (= 0,4 epoxide equivalent) are added over. the course of 30 minutes whilst stirring, the reaction temperature being kept at betv/een 110 and 120°C. After a further 30 minutes, 120· g of n-butylglycol are added. After allowing-' the mixture to cool whilst stirring, a clear solution of medium viscosity is obtained. The amino group content of this solution is 3.95 equivalents/kg.
101.2 g of the solution from b) (= 0.4 amine equivalent) are warmed to 55°C internal temperature, and a solution of 47.2 g (= 0.1 epoxide equivalent) of the epoxide described under a) and 47.2 g of n-butylglycol is then allowed to run in over the course of 1.hour. 40 minutes thereafter, a
sample gives a clear solution in glacial acetic acid : water = 1 : 15. 24 g of glacial acetic acid and 260 g of butyl- .
glycol are now added and the mixture is further stirred until cold. A clear, mobile solution of 20 °/o solids content is
obtained .
Example 1. . - 3 g of a preparation according to Instruction A, dissolved in 30 ml of ethanol, are added to a solution of 10 g of an adduct of 1 mol of p-tert .-nonylphenol and 5 mols of ethylene oxide in 970 ml of perchloroethylene, whilst stirring. 30 g of wool yarn are treated for 60. minutes at 40°C with the stable dispersion thus obtained. After removing excess .liquor by centrifuging, drying and fixing takes place over the course of a further hour at 80°C. The wool yarn treated in this way has a non-felting finish.
Example 2
6 g of a preparation according. to Instruction B, dissolved in 50 ml of methanol, are added to a solution of 10 g of an adduct of 1 mol of p-tert . -nonylphenol and 5 mols of ethylene oxide in 350 ml of perchloroethylene, whilst-, stirring. 60 g of wool yarn are treated for 40 minutes at 65°C with the stable dispersion thus obtained. After removing excess liquor by centrifuging, drying and fixing takes place over the course of 50 minutes at 80°C.
The wool yarn treated in this way has a non-felting finish.
A non-felting finish of similar quality is obtained if instead of perchloroethylene 1, 1, 1-trichloroethane is used., as the solvent.
Example 3
4' g of a preparation according to Instructio C, together with 0.4 g of an optical brightener of formula..
and 5 S of glacial acetic acid are v/orked into a dough
with 5 S of an adduct of 1 mol of p-tert .-nonylphenol and 5 raols of ethylene oxide,- and this mixture is then made up to 1000 ml with trichloroethylene . Brief stirring- yields a stable dispersion, wit which 4-0 g of bleached wool yarn are treated for 30 minutes at 70°C. After removing excess liquor by centrifuging, drying and fixing takes place over the course of a further 4-5 minutes at 80°G. The wool yarn treated in this way .has a non-felting finish and is optically brightened.
Example 4- 30 g of a preparation according' to one of'
Instructions A to D together with 60 g of one of the . - ' surface-active agents of the composition given below are worked into a dough and diluted to 6000 ml with high-boiling petrol (boiling range 155 to 195°C)« Brief stirring yields a stable dispersion. 300 g of a knitted woollen piece are treated with this liquor for 20 minutes at 20°C. After · removing the liquor by centrifuging, the piece is dried and the finish is. fixed over the course of 3 days at room
temperature. The knitted piece is non-felting.
The following products are used as surface-active •agents : - I: Condensation product of 1 mol of coconut fatty acid . and 2' mols of diethanolamine , containing about 2% of water and 2% of acetic acid.
II: Acid phosphoric acid ester of a condensation ; product of 1 mol of 2-e hylhexanol . and 5 mols of ethylene ! oxide, neutralised with sodium hydroxide, in the form- of : an 80% strength aqueous solution. '
III: Aqueous solution containing: 38.5% of an oleic '
acid polyglycol ester, 38. % of a condensation product of
1 mol of p-tert.-octylphenol and 8 mols of ethylene oxide, and 15.5% of oleic acid. . · . j
!
Example 5 ■ !
g of a preparation according to one of
Instructions A to D are worked into a dough with 15 g of
one of the surface-active agents of the composition indi- I cated in example 4·, and this mixture is then diluted to
300 ml with cyclohexane. 100 g of a woollen tricot are
treated with this liquor for 30 minutes at 5°C. After
removing excess liquor by centrifuging and drying, fixing is carried out for 1 minute at 1 0°C. The woollen tricot is non-felting. ,
Example 6
4- g of a preparation according to one of Instructions A to D are worked into a dough with 2 g of one of the
surface-active agents of the composition indicated in
example 4-, and this mixture is then diluted with perchlor-' ethylene to 460 ml. 20 g of wool yarn is treated with this , . liquor for 50 minutes at J>0 C. After, removing excess liquor by
! centrifuging, drying and fixing takes place for 10 minutes at · 1
100°C. The wool yarn is non-felting.
Claims (15)
1. Process for the finishing of textiles, especially for rendering wool non-felting, characterised in that . the textiles are treated with a preparation which (1) in a water- j insoluble organic solvent,, contains (2) a reaction product | of a)a') a basic , polyamide and a") an epoxide, an alkyl
ether of an aminoplast precondensate or an epoxide-polymeric unsaturated fatty acid reaction product, or b)b') i an epoxide-organic carboxylic acid reaction product and b") ! an amine or amino-epoxide reaction product and ( 3) a surface-active dispersing agent which is soluble. in organic solvents, that the solvent is subsequently removed from the textiles ; thus treated, and that thereafter the textiles, if desired, are j subjected to an after-treatment at room temperature or
elevated temperature.
2. Process according to Claim 1,. characterised in that the textiles are treated by the exhaustion process.
3 · Process according to Claim 2, characterised in that ! the preparation is allowed to act on the textiles at 20 to · i
80°C. j I . Process according to Claim 2, characterised in that ;
i the heat treatment is carried out at 4-0 to 100°C. j 5· Process according to one of Claims 1 to , j characterised in that a low molecular aliphatic carboxylic j acid is added to the preparation for the finishing of J textiles.
6.. Process according to Claim 1, characterised in tha petrol hydrocarbons, benzene, halogenated benzenes or
benzenes substituted by lower alkyl groups, alicyclic hydro-carbons or halogenated aliphatic hydrocarbons are used as J
organic solvents.
7· Process according to Claim 6, characterised in that trichloroethylene or perchloroethylene are used.
8. Process according to Claim 1, characterised in that, as component (2), a reaction product of a)a') a basic
polyamide from polymeric, unsaturated fatty acids and poly-alkylenepolyaiaines , . and a") an epoxide or an aminoplast.
precondensate containing alkyl ether groups, or b)b') a reaction product of an epoxide, which per molecule contains at least 2 epoxide groups, and an organic carboxylic acid, which per molecule contains at least 2 carboxyl groups, and b") an amine containing at least two amino groups or a
reaction product of an amine containin at least 2 amino groups per molecule with an epoxide containing at least 2 epoxide groups per molecule, is used. ■
9. Process according'to Claim 8, characterised in. that, as component (2), a reaction product is used which is obtained by reacting epoxides in an equivalent ratio of 1 : 1 to 1 : 5». with basic polyamides from polymeric, preferably dimeric to trimeric, unsaturated fatty acids and polyalkylenepolyamines in the presence of organic solvents at temperatures of at most 80°C, to give polyaddition compounds which are soluble or dispersible in water, and ensuring, through the addition of acid, not later than on completion of the reaction, that a sample of ' the reaction mixture has a pH-value of 2 to 8 after addition of water.
10.. Process according to Claim 8, characterised -in that, as component (2), a reaction product is used which is obtained by reacting aminoplastic precondensates containing alkyl-ether groups, in the presence of organic solvents,
35610/2
wit basic polyamldes from polymeric unsaturated fatty
acids and pOlyalkylenepolyamines to give water-soluble
compounds» and ensuring, through the addition of acid, not later than ImmOdiately on completion of the reaction, that a sample of the reaction mixture has a pH-value of 2 to 8 after addition of water.
11, Process according to Claim 8, characterised in that, as component (2), a reaction product is used which is obtained by reacting b) br) a reaction product of at least one epoxide which contains at least two epoxide groups er molecule, and at least one organic carboxlyic acid, which contains at least 2 carboxyl groups pe molecule, with the equivalent ratio of epoxide groups to acid groups being 1 : 0.1 to
1 : 0,8, with b") an amine containing at least two amino groups, wherein the amino groups each possess at least one hydrogen atom bonded to nitrogen, or a reaction product of said amine with a epoxide, which per molecule contains a least two epoxide groups and wherein the equivalent ratio of hydrogen, bonded to amine nitrogen, to epoxide groups is
3 : 1 to 11 : 1, in the presence of an organic solvent, the equivalent ratio of epoxide groups to hydrogen bonded to amine nitrogen being 1 : 2 to 1 : 10, and ensuring, through addition of acid, not later than on completion of the reaction, that a sample of the reaction mixture has a pH-value of 2 to 8 after dilution with water.
12, Xvooeee- according to Claim 1, characterised in that, as an organo-soluble surface-active dispersing agent, non-ionic or anionic compounds are used, especially those which are obtained by addition of ethylene oxide to long-chain amines, alcohols, phenols or fatt acid esters.
13. Process according to one of Claims 1 to 12, characterised in that the reaction product in the form of a solution in a polar organic solvent is used as component (2).
14. The preparations used for carrying out the process according to one of Claims 1 to 13 ♦
15. The textiles finished according to one of Claims' 1 to 12.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1665869 | 1969-11-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL35610A0 IL35610A0 (en) | 1971-01-28 |
| IL35610A true IL35610A (en) | 1973-10-25 |
Family
ID=4419141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL35610A IL35610A (en) | 1969-11-10 | 1970-11-09 | Process for the finishing of textiles |
Country Status (2)
| Country | Link |
|---|---|
| IL (1) | IL35610A (en) |
| ZA (1) | ZA707478B (en) |
-
1970
- 1970-11-04 ZA ZA707478A patent/ZA707478B/en unknown
- 1970-11-09 IL IL35610A patent/IL35610A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA707478B (en) | 1971-07-28 |
| IL35610A0 (en) | 1971-01-28 |
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