EP1177343A1 - Wässrige zusammensetzung zur filzfreiausrüstung von wolle - Google Patents
Wässrige zusammensetzung zur filzfreiausrüstung von wolleInfo
- Publication number
- EP1177343A1 EP1177343A1 EP00912594A EP00912594A EP1177343A1 EP 1177343 A1 EP1177343 A1 EP 1177343A1 EP 00912594 A EP00912594 A EP 00912594A EP 00912594 A EP00912594 A EP 00912594A EP 1177343 A1 EP1177343 A1 EP 1177343A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- wool
- polyisocyanate
- composition according
- prepolymer
- 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 54
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 238000010006 anti-felting Methods 0.000 title abstract 2
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 30
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 30
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 26
- 229920005862 polyol Polymers 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 229920000570 polyether Polymers 0.000 claims description 14
- 150000003077 polyols Chemical class 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- -1 alkylene glycol Chemical compound 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 4
- 229930003427 Vitamin E Natural products 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011709 vitamin E Substances 0.000 claims description 3
- 235000019165 vitamin E Nutrition 0.000 claims description 3
- 229940046009 vitamin E Drugs 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 35
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000009950 felting Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 229940001482 sodium sulfite Drugs 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- OWXXKGVQBCBSFJ-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]ami Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 OWXXKGVQBCBSFJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- OVZITGHGWBXFEA-UHFFFAOYSA-N Pyridinitril Chemical compound ClC1=NC(Cl)=C(C#N)C(C=2C=CC=CC=2)=C1C#N OVZITGHGWBXFEA-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/572—Reaction products of isocyanates with polyesters or polyesteramides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/568—Reaction products of isocyanates with polyethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/10—Animal fibres
- D06M2101/12—Keratin fibres or silk
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/45—Shrinking resistance, anti-felting properties
Definitions
- the present invention relates to an aqueous
- composition for the non-felt finishing of wool or textiles containing wool and a method for the non-felt finishing of wool or materials containing wool.
- wool mattes with changing mechanical loads in the moist state. Since irreversible dimensional changes (shrinking) and a deterioration in the appearance of the goods occur when felting, wool is generally provided with a felt-free finish.
- a number of processes are already known for this purpose, namely chlorination processes, oxidation processes, enzymatic, alkaline processes and synthetic resin processes. The latter also includes felt-free finishing with self-crosslinking polyurethanes (PU).
- PU self-crosslinking polyurethanes
- the prepolymer can be crosslinked thermally and / or chemically (e.g. pH change or polarization reversal by adding electrolyte).
- GB 1,419,306 A describes a process for the preparation of bisulfite addition products of polyisocyanates, water-insoluble polyisocyanate prepolymers with at least two isocyanate groups and a bisulfite being reacted.
- the polyisocyanate prepolymers can be obtained by Reaction of polyisocyanates with hydroxyl group-containing compounds, which may be polyethers, polyesters, polythioethers, mixed polyester-polyethers or mixed polyether-polythioethers.
- Preferred compounds containing hydroxyl groups are polyethers, such as polypropylene glycol started on glycerol.
- the use of a water-miscible organic solvent, such as lower alcohols, is essential for the preparation of the polyisocyanate prepolymers.
- the bisulfite-capped polyisocyanate prepolymers obtained are used for the shrink-proofing of wool by applying them to the fabric and then curing them at a higher temperature.
- the present invention is therefore based on the object to provide a composition and a process for the non-felting of wool, in which no solvent is used and the odor nuisance by sulfur dioxide is reduced (here and in the following, the term wool also includes materials containing wool. These are explained in more detail below) .
- the invention is also based on the object of improving the hardening of the handle of the wool in the felt-free finish.
- the present invention therefore relates to an aqueous composition which comprises a bisulfite-capped polyisocyanate prepoly which, based on the uncapped state, is composed of
- An aliphatic polyether polyol in particular a poly-C 1 -C 4 -alkylene oxide or poly-C 2 -C 4 -alkylene glycol, is preferably used as the polyether polyol.
- Polyethylene glycol or polypropylene glycol are particularly preferred.
- the average molecular weight of the polyether polyol is preferably in the range from 400 to 4000, in particular 800 to 2000.
- the hydroxyl functionality is generally in the range from 2 to 4, preferably in the range from 2 to 3.
- the proportion by weight of the polyether polyol is preferably 10 to 30% by weight, based on the prepolymer.
- the polyester polyol is, in particular, hydroxyl-functional polyester based on aliphatic or aromatic polycarboxylic acids, in particular dicarboxylic acids, and aliphatic polyols, in particular diols.
- Aliphatic dicarboxylic acids such as succinic acid, adipic acid, pimelic acid, are preferred.
- Suitable aromatic dicarboxylic acids are phthalic acid, isophthalic acid and terephthalic acid.
- Usable aliphatic polyols are in particular ethylene glycol, propylene glycol and the oligomers thereof, such as di-, tri- or tetraethylene glycol or di-, tri- or tetrapropylene glycol,
- polyester polyols are also products which can be obtained by reacting polyols, in particular diols or triols, and hydroxycarboxylic acids.
- Polyols suitable for this purpose are in particular the aliphatic polyols mentioned.
- Suitable hydroxycarboxylic acids are, for example, glycolic acid, lactic acid, hydroxybutyric acid, hydroxyvaleric acid and hydroxybenzoic acid.
- the average molecular weight of the polyester polyol is generally in the range from 500 to 6000, preferably 3000 to 4000. Its hydroxyl functionality is generally in the range from 2 to 4, preferably 2 to 3. It is preferably used in a proportion of 40 to 80% by weight. % used.
- the polyisocyanate is preferably a diisocyanate.
- Aromatic or aliphatic diisocyanates can be used.
- Aromatic diisocyanates which can be used are 2,4-toluenediisocyanate, 2,6-toluenediisocyanate and mixtures thereof, and 4,4'-diphenylmethane diisocyanate.
- Suitable aliphatic diisocyanates are isophorone diisocyanate, cyclohexane-1,4-diisocyanate and 4,4'-methylene bis (cyclohexyl isocyanate). However, diisocyanates are preferred of the formula
- n is 2 to 8, in particular 4 to 8.
- Tetramethylene diisocyanate and in particular hexamethylene diisocyanate are particularly preferred.
- the proportion of polyisocyanate is preferably 10 to 20% by weight. Its NCO value is preferably in the range from 3 to 4.5, in particular 3.3 to 4.0.
- the further component d) is in particular compounds having at least one hydroxyl, amino or mercapto group.
- mono alcohols such as methanol, ethanol, etc .
- low molecular weight diols such as ethylene glycol, propylene glycol
- Mono- or diamines such as 1,6-hexanediamine, ethylenediamine, etc .
- Amino alcohols such as 2-aminomethyl propanol, thiols such as butyl mercaptan etc.
- Component d) is preferably used in an amount of at least 0.1% by weight and in particular 0.5 to 20% by weight.
- the polyisocyanate prepolymers are prepared by simultaneously reacting the components without using a solvent.
- the reaction takes place at elevated temperature, in particular at a temperature in the range from 60 to 120 ° C.
- the reaction mixture is cooled, but only to the extent that it is still in the form of a melt.
- the polyisocyanate prepolymer is then dispersed in the form of the melt in an aqueous bisulfite solution.
- an alkali metal or alkaline earth metal bisulfite for example sodium or potassium bisulfite, is used in particular as the bisulfite.
- the bisulfite based on the NCO number of the prepolymer, is used in excess.
- An excess of 10 to 80 mol%, in particular 30 to 40 mol%, of bisulfite is preferably used.
- the bisulfite is presented in the form of an aqueous solution in which the melt of the polyisocyanate prepolymer is dispersed.
- the dispersion is carried out in a conventional manner, for example using a high-speed stirrer or an Ultra-Turrax.
- the concentration of the bisulfite solution is generally in the range from 1 to 20, preferably 2.8% to 10% by weight, preferably 3.0% to 8% by weight.
- the reaction of the bisulfite solution with the polyisocyanate prepolymer takes place at the lowest possible temperature, generally at a temperature of less than 50 ° C., in particular less than 40 ° C.
- the temperature is generally at least about 5 to 10 ° C above the solidification range of the polyisocyanate prepolymer.
- the reaction is complete when, for example, it is no longer possible to detect isocyanate groups by means of IR chromatography.
- the pH of the dispersion is adjusted to a value in the range from 5 to 7, in particular 5 to 6, for example by adding alkali metal sulfite or alkali metal bisulfite solution.
- composition according to the invention particularly preferably additionally contains a radical inhibitor.
- radical inhibitors are preferably sterically hindered phenols,
- Hydroquinones, anilines and phosphites Hydroquinones, anilines and phosphites (antioxidants). Examples are di-t-butylhydroquinone, and the Irganox and Irgafos types, Chimassorb and Timuvin types from Ciba, such as Irganox 245, 1010, 1035, 1076, 1098, 5057, Irgafors 168, Irgafos TNPP, TPP and DDPP, Chimassorb 119 and 944, Tinuvin 123, 144, 770 and 791. It is preferred to use a tocopherol and particularly preferably vitamin E ( ⁇ -tocopherol ).
- the radical inhibitor is preferably added after the preparation of the polyisocyanate prepolymer.
- the amount of radical inhibitor is generally 0.05 to 5% by weight, preferably 0.1 to 3% by weight, based on the polyisocyanate prepolymer.
- a liquor is prepared for use by diluting the compositions according to the invention with water to a content of 20 to 200 g, preferably 30 to 100 g and in particular 50 to 90 g of the capped isocyanate group-containing prepolymer per liter of liquor.
- the liquor can contain customary additives and auxiliaries, such as surfactants, defoamers, wetting agents, deaerators, plasticizers etc., such as cotton, polyester, polyamide etc.
- the pH is adjusted to a value in the range from 4 to 9, preferably 5 to 8 with an acid such as HCl, NaHS0 3 etc. or a base such as NaOH.
- the wool fabric to be treated is then impregnated with the liquor in the customary manner, for example using the customary application method mentioned at the outset
- Impregnation devices such as a foulard.
- the tissue is squeezed to a liquor absorption of about 30 to 120% and the squeezed tissue is then subjected to a heat treatment at a temperature in the range from 100 to 190 ° C., preferably 120 to 180 ° C. and in particular 140 to 180 ° C. subject.
- the tissue is dried by the heat treatment and at the same time the capped prepolymer is cured, ie the prepolymer is crosslinked with the wool fibers.
- the duration of the heat treatment depends on the concentration of the liquor, the liquor intake and the treatment temperature. In general, the heat treatment is carried out for a period of 10 to 300 seconds, in particular 30 to 160 seconds.
- Another possibility of applying the capped prepolymer to wool is to prepare a liquor with water which contains 2-6% by weight (based on the mass of the wool article to be finished) of the capped isocyanate group-containing prepolymer.
- the wool article is soaked over a period of 10-60 min, in particular 15-30 min, with the treatment liquor in suitable equipment (e.g. reel skids; roller skids; paddles; etc.) and then squeezed off as indicated above.
- the opening of the capped prepolymer and the simultaneous crosslinking can also be carried out by alkaline pH adjustment in the range from pH 7.1-12.0, in particular pH 8.0-10.0 and / or by polarization reversal of the wool surface (reversal of the negative zeta potential into a positive one) by appropriate addition of electrolyte, in particular of alkali and alkaline earth metal compounds, such as sodium sulfate, sodium chloride, magnesium sulfate, magnesium chloride etc.
- wool and wool-containing materials i.e. Treat blends of wool and other textile fibers such as cotton, polyester, polyamide, etc. Treatment can be carried out at any stage and type of processing, e.g. as a sliver, yarn, fabric, knitted fabric or finished textiles.
- the fabrics treated in this way have a wash-resistant felt-free finish, i.e. very little warp shrinkage and weft shrinkage can be observed.
- the reaction mixture is stirred at room temperature for 12 hours until the reaction of the sulfite with the isocyanate has ended.
- the pH must have reached 5.6 at the end of the reaction time. Otherwise, the pH should be corrected by adding 4% sodium sulfite solution or sodium bisulfite solution.
- the product is used for the felt-free finish according to Examples 3-9.
- Example 1 The following amounts of raw material are reacted in accordance with Example 1: 80 g of polyether polyol, 790 g of polyester polyol and 130 g of hexamethylene diisocyanate.
- the melt obtained can be do not emulsify in the aqueous bisulfite solution with this composition without the addition of solvent.
- Comparative Example 2 The reaction is carried out analogously to Example 1. The following raw materials are used:
- Example 2 50 g / 1 product according to Example 1 are diluted with cold water and adjusted to pH 7.0 with sodium hydrogen carbonate. Furthermore, 1 g / l of a nonionic wetting agent based on a phosphoric acid ester is added to the liquor. With this fleet, a medium-weight woolen fabric is soaked in a foulard chassis, which is squeezed by the pad squeezer to a fleet absorption of 70%. Then this with the
- Treatment liquor through wetted wool fabrics is tension-free dried on a stenter at 160 ° C.
- the dwell time in the stenter is 120 s.
- the wool fabric equipped in this way has a warp shrinkage of -3.3% according to the test washing program of the IWS (International Wool Secretariat) for the superwash equipment (see TM 31 of the IWS as of July 1996, which is based on ISO 6330) a shot shrinkage of -3.7%.
- the same woolen fabric exhibits a warp shrinkage of -23.3% and a weft shrinkage of -22.1% without being equipped with the product.
- Example 3 Analogously to Example 3, a treatment liquor with the product according to Example 1 is set up. However, the concentration in this fleet is 60 g / 1. The finishing of the wool fabric of the same type with the treatment liquor is carried out as described in Example 3. The wool fabric thus finished has a warp shrinkage of -2.8% and a weft shrinkage of -2.5% according to the IWS test wash program for the Superwash finish (TM 31).
- Example 3 Analogously to Example 3, a treatment liquor with the product according to Example 1 is set up. However, the concentration in this fleet is 70 g / 1.
- the wool fabric of the same type is finished with the treatment liquor as described in Example 3.
- the wool fabric thus finished has a warp shrinkage of -1.9% and a weft shrinkage of -1.5% according to the IWS test wash program for the Superwash finish (TM 31).
- a liquor with 70 g / 1 product according to Example 1 and 1 g / 1 nonionic wetting agent based on a phosphoric acid ester is prepared with cold water.
- the pH of the liquor is adjusted to pH 6.6 using sodium hydrogen carbonate.
- a medium-weight woolen fabric is soaked in a foulard chassis, which is squeezed by the pad squeezer to a fleet absorption of 70%.
- This wool fabric, which is wetted with the treatment liquor, is then dried without tension on a stenter at 160 ° C.
- the dwell time in the stenter is 120 s.
- the wool fabric thus finished shows for the superwash finish according to the IWS test wash program (TM 31) a warp shrinkage of -2.5% and a weft shrinkage of -4.3%.
- Example 7 Analogously to example 6, a treatment liquor with the product according to example 1 is set up. However, the liquor is adjusted to pH 7.0 with sodium hydrogen carbonate instead of pH 6.6. The finishing of the wool fabric of the same type with the treatment liquor is carried out as described in Example 6. The wool fabric thus finished has a warp shrinkage of -1.7% and a weft shrinkage of -3.1% according to the IWS test wash program for the Superwash finish (TM 31).
- Example 8 Analogously to Example 6, a treatment liquor with the
- Example 6 Product prepared according to Example 1. However, the liquor is adjusted to pH 7.4 instead of pH 6.6 with sodium hydrogen carbonate.
- the finishing of the wool fabric of the same type with the treatment liquor is carried out as described in Example 6.
- the wool fabric thus finished has a warp shrinkage of -0.9% and a weft shrinkage of -1.2% according to the IWS test wash program for the Superwash finish (TM 31).
- Example 9 A liquor with 70 g / 1 product according to Example 1 and 1 g / 1 nonionic wetting agent based on a phosphoric acid ester is prepared with cold water. The pH of the liquor is adjusted to pH 7.4 using sodium hydrogen carbonate. With this fleet, a medium-weight woolen fabric is soaked in a foulard chassis, which is squeezed by the pad squeezer to a fleet absorption of 70%. This wool fabric, which is wetted with the treatment liquor, is then dried without tension on a stenter at 160 ° C. The dwell time in the stenter is 120 s.
- the wool fabric thus equipped has a warp shrinkage according to the IWS test wash program for the Superwash finish (TM 31) of -1.5% and a shot shrinkage of -0.5%.
- a liquor with 60 g / 1 product according to comparative example 3 and 1 g / 1 nonionic wetting agent based on a phosphoric acid ester is prepared with cold water.
- the pH of the liquor is adjusted to pH 7.2 using sodium hydrogen carbonate.
- a medium-weight woolen fabric is soaked in a foulard chassis, which is squeezed by the pad squeezer to a fleet absorption of 70%.
- This wool fabric, which is wetted with the treatment liquor, is then dried without tension on a stenter at 160 ° C.
- the dwell time in the stenter is 90 s.
- the wool fabric thus finished has a warp shrinkage of -23.3% and a weft shrinkage of -22.6% according to the IWS test wash program for the Superwash finish (TM 31).
- Example 3 Analogously to Example 3, a treatment liquor with the product according to Comparative Example 2 is set up. The wool fabric of the same type is finished with the treatment liquor as described in Example 3.
- the wool fabric thus finished has a warp shrinkage of -11.9% and a weft shrinkage of -14.7% according to the IWS test wash program for the Superwash finish (TM 31).
- Example 4 Analogously to Example 4, a treatment liquor with the product according to Example 2 is set up.
- the wool fabric of the same type is finished with the treatment liquor as described in Example 4.
- the wool fabric thus finished has a warp shrinkage of -0.3% and a weft shrinkage of -2.1% according to the IWS test wash program for the superwashing equipment (TM 31).
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19919816A DE19919816A1 (de) | 1999-04-30 | 1999-04-30 | Wässrige Zusammensetzung zur Filzfreiausrüstung von Wolle |
DE19919816 | 1999-04-30 | ||
PCT/EP2000/002143 WO2000066830A1 (de) | 1999-04-30 | 2000-03-10 | Wässrige zusammensetzung zur filzfreiausrüstung von wolle |
Publications (2)
Publication Number | Publication Date |
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EP1177343A1 true EP1177343A1 (de) | 2002-02-06 |
EP1177343B1 EP1177343B1 (de) | 2003-08-27 |
Family
ID=7906482
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Application Number | Title | Priority Date | Filing Date |
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EP00912594A Expired - Lifetime EP1177343B1 (de) | 1999-04-30 | 2000-03-10 | Wässrige zusammensetzung zur filzfreiausrüstung von wolle |
Country Status (3)
Country | Link |
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EP (1) | EP1177343B1 (de) |
DE (2) | DE19919816A1 (de) |
WO (1) | WO2000066830A1 (de) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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DE50308762D1 (de) * | 2002-07-05 | 2008-01-24 | Dystar Textilfarben Gmbh & Co | Wässrige Zusammensetzung zur Filzfreiausrüstung von Wolle |
ITVA20050031A1 (it) * | 2005-05-13 | 2006-11-14 | Lamberti Spa | Bagni di filatura |
DE102010002558A1 (de) | 2009-11-20 | 2011-06-01 | Symrise Ag | Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe |
CN101906201B (zh) * | 2010-07-01 | 2012-07-18 | 东华大学 | 一种采用纳米纤维素改性制备聚氨酯整理剂的方法 |
ES2861268T3 (es) | 2011-09-20 | 2021-10-06 | Basf Se | Moduladores de bajo peso molecular del receptor de mentol frío TRPM8 y su uso |
ES2967435T3 (es) | 2017-08-31 | 2024-04-30 | Basf Se | Uso de principios activos refrescantes fisiológicos y productos que contienen dichos principios activos |
CN109485828B (zh) * | 2018-11-03 | 2021-04-02 | 东华大学 | 一种新型水溶性封端异氰酸酯的合成方法 |
WO2022105986A1 (de) | 2020-11-17 | 2022-05-27 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2023143741A1 (de) | 2022-01-28 | 2023-08-03 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
Family Cites Families (4)
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DE2414470B2 (de) * | 1974-03-26 | 1977-01-13 | Bayer Ag, 5090 Leverkusen | Waessrige loesung eines bisulfitblockierten polyisocyanatvorpolymeren |
DE2837083A1 (de) * | 1978-08-24 | 1980-03-06 | Bayer Ag | Verfahren zur filzfreiausruestung von textilgut aus keratinhaltigen fasern |
US4433017A (en) * | 1981-09-17 | 1984-02-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Thermally reactive water-soluble blocked urethane prepolymer |
US5306435A (en) * | 1991-07-11 | 1994-04-26 | Nihon Junyaku Co., Ltd. | Treating agent composition for leather, for fibrous materials |
-
1999
- 1999-04-30 DE DE19919816A patent/DE19919816A1/de not_active Withdrawn
-
2000
- 2000-03-10 EP EP00912594A patent/EP1177343B1/de not_active Expired - Lifetime
- 2000-03-10 DE DE50003452T patent/DE50003452D1/de not_active Expired - Fee Related
- 2000-03-10 WO PCT/EP2000/002143 patent/WO2000066830A1/de active IP Right Grant
Non-Patent Citations (1)
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See references of WO0066830A1 * |
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Publication number | Publication date |
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DE19919816A1 (de) | 2000-11-02 |
DE50003452D1 (de) | 2003-10-02 |
EP1177343B1 (de) | 2003-08-27 |
WO2000066830A1 (de) | 2000-11-09 |
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