CN1145371A - 头发化妆品用的可溶性共聚物 - Google Patents
头发化妆品用的可溶性共聚物 Download PDFInfo
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- CN1145371A CN1145371A CN95120363A CN95120363A CN1145371A CN 1145371 A CN1145371 A CN 1145371A CN 95120363 A CN95120363 A CN 95120363A CN 95120363 A CN95120363 A CN 95120363A CN 1145371 A CN1145371 A CN 1145371A
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- monomer
- weight
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- multipolymer
- vinyl
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 6
- 239000003676 hair preparation Substances 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract description 63
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims abstract description 7
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 6
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 21
- -1 N-vinyl pyrrole ketone Chemical class 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- RYPYDIHMPGBBJN-UHFFFAOYSA-M sodium;2-methyl-1-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].CC(C)C(S([O-])(=O)=O)NC(=O)C=C RYPYDIHMPGBBJN-UHFFFAOYSA-M 0.000 claims 1
- 229920001567 vinyl ester resin Polymers 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 abstract description 11
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
- 239000000243 solution Substances 0.000 description 46
- 239000003999 initiator Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- ZGHNHKVUNFYLAY-UHFFFAOYSA-N CC=NC(=O)N(C=C)C=C Chemical compound CC=NC(=O)N(C=C)C=C ZGHNHKVUNFYLAY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 4
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000005502 peroxidation Methods 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 2
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical class CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- NNNLYDWXTKOQQX-UHFFFAOYSA-N 1,1-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)(OC(=O)C=C)OC(=O)C=C NNNLYDWXTKOQQX-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- ZHCGVAXFRLLEFW-UHFFFAOYSA-N 2-methyl-3-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)CNC(=O)C=C ZHCGVAXFRLLEFW-UHFFFAOYSA-N 0.000 description 1
- TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 description 1
- FHBWGXDQIOWTCK-UHFFFAOYSA-N 2-methylpentanenitrile Chemical compound CCCC(C)C#N FHBWGXDQIOWTCK-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- PVFBZMGUZNPMBO-UHFFFAOYSA-N COC(C)=O.NC(=N)N Chemical class COC(C)=O.NC(=N)N PVFBZMGUZNPMBO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-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
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 230000003370 grooming effect Effects 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- GRJAYPIBCLZQMH-UHFFFAOYSA-N n-[1-(prop-2-enoylamino)butyl]prop-2-enamide Chemical compound C=CC(=O)NC(CCC)NC(=O)C=C GRJAYPIBCLZQMH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- WJXKWIFHRZWPET-UHFFFAOYSA-N tert-butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(C)(C)C WJXKWIFHRZWPET-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Cosmetics (AREA)
Abstract
K值为30-50的共聚物是在醇溶液中由下列组分进行游离基溶液聚合获得：A)15-84.99％(重量)的至少一种选自N-乙烯基吡咯烷酮，N-乙烯基己内酰胺和N-乙烯基咪唑的单体，B)15-84.99％(重量)还能进行游离基共聚合单烯属不饱和单体和C)0.01-2％(重量)至少一种能进行游离基共聚合并具有至少二个非共轭烯属双键的单体。
Description
本发明涉及具有K值为30-50的共聚物：它由
A)15-84.99％(重量)至少一种选自N-乙烯基吡咯烷酮，N-乙烯基已内酰胺和N-乙烯基咪唑的单体，
B)15-84.99％(重量)还能进行游离基共聚合的单烯属不饱和单体和
C)0.01-2％(重量)至少一种能进行游离基共聚合并具有至少二个非共轭烯属双键的单体在醇中进行游离基溶液聚合获得。
本发明还涉及制备所述共聚物及其用于头发化妆品中。
适宜作为头发化妆品的成膜剂的，基于N-乙烯基化合物和丙烯酸酯及由在醇中进行游离基溶液聚合制备的聚合物已公开在，例如德国公开申请DOS3.627,969，DE-A-3312668，DE-A-3627970和DE-A-4013872中。
DE-A-2814287公开了N-乙烯基咪唑共聚物，它可以含少于5％(摩尔)具有2个或更多可共聚合双键的共聚单体，这些共聚单体导致三维交联的聚合物。这些共聚物是在水、水/甲醇混合物或有机溶剂、例如甲苯中制备。这些共聚物适合在去垢剂中作抑制褪色的涤加剂。
适宜作为头发化妆品中成膜剂的和基于N-乙烯基化合物和丙烯酸酯的聚合物通常是由在醇溶液中游离基溶液聚合制备的，使用的溶剂特别是在化妆品中常规应用的溶剂，例如乙醇和/或异丙醇，如果需要的话为和水的混合物。
由于这些醇的调节分子量的特性，具有相对高K值，例如35-45的聚合物的特殊制备可能存在困难。相对高K值能由仅在相当低溶剂浓度的已知工艺中达到，此方法可导致排热问题，特别是在生产规模。
另一方面，这种相当高分子量的聚合物在头发上具有较好定型性能。
本发明目的是提供适合于头发化妆品中相对高分子量成膜聚合物，它能简单地由在通常用在化妆品中的醇中进行游离基溶液聚合获得并易溶于这些醇中。
我们已经发现本发明目的是由上述定义的共聚物和它们的制备方法，它们的应用和含这些共聚物的头发用化妆组合物达到的。
按照本发明，适宜的单体A)是选自N-乙烯基吡咯烷酮，N-乙烯基已内酰胺和N-乙烯基咪唑和它们的混合物的杂环N-乙烯基化合物。优选的单体A)是N-乙烯基吡咯烷酮和N-乙烯基己内酰胺。
单体A)的使用量为15-84.99，优选为20-80％(重量)。
按照本发明，适宜的单体B)是能进一步游离基共聚合的单烯属不饱和化合物；或它们的混合物，例如饱和的C2-C24单羧酸乙烯酯，如醋酸乙烯酯或丙酸乙烯酯，或相对长链脂肪酸，例如十二碳酸或硬脂酸的乙烯酯，或者支链脂肪酸，如新戊酸或Versatic酸(商品名)的乙烯酯。
丙烯酸或甲基丙烯酸的C1-C10烷基酯，例如丙烯酸乙酯，丙烯酸异丁酯，丙烯酸正丁基酯。丙烯酸叔丁酯，甲基丙烯酸甲酯，甲基丙烯酸乙酯，甲基丙烯酸异丁酯或甲基丙烯酸正丁酯，或相应的氨烷基醇的酯例如甲基丙烯酸N，N-二甲基氨基乙酯也是适用的。
其它适合的单体B)是含磺酸盐基的单体，例如3-丙烯酰氨基-2-甲基丙磺酸的盐或2-丙烯酰氨基-2-甲基丙磺酸的盐或最好是相应的钠盐。
优选的单体(B)是醋酸乙烯酯和丙烯酸叔丁酯。
按照本发明，单体B)的使用量为15-84.99，优选为20-80％(重量)。
适宜的单体C)是能进行游离基共聚合和在分子中含至少二个非共轭烯属双键的单体。适宜的单体的例子是饱和多元醇的丙烯酸酯或甲基丙烯酸酯，例如1，4-丁二醇二丙烯酸酯，1，6-已二醇二丙烯酸酯，四甘醇二丙烯酸酯，三甲基醇丙烷三丙烯酸酯，三丙二醇二丙烯酸酯，季戊四醇三丙烯酸酯，季戊四醇四丙烯酸酯，乙二醇二甲基丙烯酸酯，二甘醇二甲基丙烯酸酯，三甘醇二甲基丙烯酸酯，四甘醇二甲基丙烯酸酯，聚乙二醇400二甲基丙烯酸酯，1，3-丁二醇二甲基丙烯酸酯，1，4-丁二醇二甲基丙烯酸酯，1，6-己二醇二甲基丙烯酸酯，1，12-十二碳二醇二甲基丙烯酸酯，新戊二醇二甲基丙烯酸酯或三甲醇丙基三甲基丙烯酸酯。
其它适宜的单体C)是甲基丙烯酸烷基酯或双酚A二甲基丙烯酸酯，以及多元醇的乙烯基醚，如丁二醇二乙烯基醚。多官能团的丙烯酰胺或甲基丙烯酰胺，如N，N′-亚甲基双丙烯酰胺，N，N′-亚甲基双甲基丙烯酰胺，N，N′-氧化双亚甲基双丙烯酰胺，N，N′苯亚甲基双丙烯酰胺，对苯二亚甲基四丙烯酰胺，N，N′-亚丁基双丙烯酰胺或双丙烯酰氨基乙酸甲酯。二乙烯基亚乙基脲也是适用的单体C)。
优选的单体C)是1，4-丁二醇二丙烯酸酯，1，6-己二醇二丙烯酸酯，四甘醇二丙烯酸酯，乙二醇二甲基丙烯酸酯，丁二醇二乙烯基醚，N，N′-亚甲基双丙烯酰胺和二乙烯基亚乙基脲。
单体C)使用的量是基于总单体混合物的0.01-2，优选0.02-0.5％(重量)。
单体C)的量最好是：单体C的摩尔量(N)，基于不使用单体C)形成的共聚物的摩尔数(P)由下述关系式表示：
P/N＝a其中a是1-5的十进数，优选是1.5-3。变量(P)能很容易地由本专业技术人员从单体A)和B)的重量和从这些量的单体A)和B)得到的聚合物的平均分子量Mn的比求出。
新的共聚物可完全溶在化妆品用醇中，如乙醇或异丙醇中，并是无凝胶的。
K值为30-50，优选为35-45，K值是按照H.Fikentscher，Cellulose Chemie，13(1932)，58-64和71-74中用1％(重量)浓度醇溶液测定的。
新的共聚物是在醇溶液中，如果需要，可在醇和水的混合物中，由游离基溶液聚合制备的。适宜的醇是C1-C4烷基醇，优选为通常用在化妆品中的乙醇和异丙醇。
聚合是在适量做为聚合引发剂的形成游离基，如有机偶氮或过氧化化合物存在下进行。
适宜的引发剂的例子是二酰基过氧化物，如二月桂酰基，二癸酰基和二辛酰基过氧化物和过酯，如过氧化新戊酸叔丁基酯，过氧化新戊酸叔戊基酯或过氧化新月桂酸叔丁基酯和偶氮化合物例如2，2-偶氮双异丁酸二甲基酯，2，2-偶氮双异丁腈，2，2-偶氮双(2-甲基丁腈)或2，2-偶氮双C2，2-二甲基戊腈)。
共聚物可由分批方法制备，但最好是进料法制备。单体混合物溶液中的一些是一开始就加入，而其余部分在几个小时内加入。单体C)最好仅通过进料加入。单体进料期间通常是在一般技术条件下能很容易除去释放的聚合热。
聚合反应在60-100℃，优选在70-85℃下有利进行。反应能在自生压力下，大气压或惰性气体超计大气压下进行。适宜的惰性气体的例子是氮。
在聚合反应后在另外的游离基引发剂存在下进行后聚合反应也是可行的。对后聚合特别适宜的游离基引发剂是通式工的化合物
R1-O-O-R2 I其中R1是4-8个碳原子的烷基和R2是氢或R1或是-R3-O-OR1，其中R3是直链或支链C4-C10亚烷基。适宜的烷基的例子是叔丁基和叔戊基。如果R2是氢，化合物是烷基氢过氧化物。适宜的游离基引发剂是，例如2.5-二甲基-2.5-双(叔丁基过氧)己烷。后聚合反应的优选的游离基引发剂是二-叔丁基过氧化物和二-叔戊基过氧化物。后聚合反应有利在110-150℃下进行，直到剩余的单体含量已达到小于50ppm为止。
新的共聚物的Fikentscher\K值为30-50，优选为35-45。它们可溶于通常用于化妆品的醇中，如乙醇或异丙醇，或它们和水的混合物中，以获得透明溶液并是无凝胶的。特别有利的用控制的方法也可获得相对高的K值，并且产生的共聚物具有良好的薄膜形成性能。
新的共聚物适合作用头发化妆配方中用作成膜剂，例如喷发胶，头发定型组合物和定型发乳。
实施例
共聚物水溶液的浊度是用浊度测定计测量(按照DIN38404的改进方法)。在这个测量方法中，在通过测量溶液后，光散射是用光度测定法测定。散射取决于光线和溶液中的颗粒或液滴之间相互作用，由其数目和粒度计算浊度。测定的可变量用浊度单位(NTU)表示并在25℃和在10％(重量)浓度水溶液中测定并用基于甲作(formazin)为人造浊度剂校准确定。NTU值越高，溶液越混浊。
溶液中N-乙烯基吡咯烷酮和醋酸乙烯酯的残余量由气体色谱法分析测定(限制测定50ppm)或液体色谱法分析(限制测定1ppm)测定。
在实施例1-3中制备的聚合物是完全无凝胶的即当刷涂聚合物溶液以形成薄膜时没有检测到凝胶颗粒。
K值在25℃下，在1.0％(重量)浓度乙醇溶液中测定。
用51搅拌实验釜进行聚合反应，这种釜由氮吹洗几乎完全无痕量氧存在。实施例1
在乙醇溶液中的30％(重量)的N-乙烯基吡咯烷酮和70％(重量)的醋酸乙烯酯的共聚物。
首先制备下列溶液
1.溶液1，由450g N-乙烯基吡咯烷酮，1050g醋酸乙烯酯和870g乙醇组成。
2.引发剂进料，由3g过氧新戊酸叔丁酯溶在100g乙醇中组成。
3.初始取的混合物，由200g溶液1和10g引发剂进料。
4.单体进料，由2120g溶液1和4g二乙烯基亚乙基脲。
把初始取的混合物加到搅拌的实验釜中，在氮气压为1.5巴下加热使内部温度为70℃，聚合反应引发后，可检测出粘度增加和放热反应，单体进料和引发剂进料同时开始。引发剂进料在8小时内恒速加入，单体进料在7小时内恒速加入。为了消除残余的单体，再保持内部温度70℃一小时。此后计量9g 2.5-二甲基-2.5-二(叔丁基过氧)己烷于580g乙醇中的溶液并关闭釜，在130℃下加热8小时。
产生的透明、无色和粘稠的溶液固体含量为50.0％，产物的K值(在1％浓度乙醇溶液中测量)为43.4，溶液具有NTU值为2.8，它在用乙醇稀释溶液使其固体含量为5％时得到的残留的单体，即N-乙烯基吡咯烷酮和醋酸乙酯两者的值都少于50ppm。对比例1
在乙醇溶液中的30％(重量)N-乙烯基吡咯烷酮和70％(重量)醋酸乙烯酯的共聚物，其具有正常K值。
首先制备下列溶液：
1.单体进料，由450g N-乙烯基吡咯烷酮，1050g醋酸乙烯酯和870g乙醇组成。
2.引发剂进料，由3g叔丁基过氧新戊酸酯溶在100g乙醇中组成。
首先取200g单体进料和10g引发剂进料入搅拌的实验釜中，使氮气压达到1.5巴及把混合物加热到内部温度为70℃。后面的工艺同实施例1。
产生透明，无色和粘稠溶液的固体含量为51.5％。产物的K值(在1％浓度乙醇溶液中测定)为28.7及溶液具有NTU值为1.5已在用乙醇稀释溶液使固体含量为5％后获得的。残留单体N-乙烯基吡咯烷酮和醋酸乙烯酯的值都少于50ppm。实施例2
具有高K值，于异丙醇溶液中的60％(重量)的N-乙烯基吡咯烷酮和40％(重量)的醋酸乙烯酯的共聚物。
首先配制下列溶液：
1.溶液1，由750g N-乙烯基吡咯烷酮，600g醋酸乙烯酯和800g异丙醇组成。
2.引发剂进料，由4g叔丁基过氧化新戊酸酯溶于100g乙醇中组成。
3.初始取用混合物，含200g溶液1和10g引发剂进料。
4.单体进料，由1950g溶液1和3g二乙烯基亚乙基脲。
把初始取的混合物加到搅拌的实验釜中，使氮气压达1.5巴并加热混合物使内部温度达70℃。在聚合反应引发后，可检测出粘度的增加和放热反应单体进料和引发剂进料同时开始。引发剂进料在8小时内以恒定速率加入，而单体进料在6小时内以恒定速率加入。在单体进料加入后，立刻在2小时内计量加入另外的150gN-乙烯基吡咯烷酮。
在加完引发剂进料后，蒸馏出250ml异丙醇。为了消除残留的单体，在8小时内，内部温度70℃下量入8克叔丁基过氧新戊酸酯于150g异丙醇中的溶液，以及再保持70℃温度4小时，在添加750g水后，用蒸气蒸馏法排出异丙醇及溶液固体含量为20％并喷雾干燥水份。
获得浅白色粉末。产品K值(1％浓度乙醇溶液测定)为37.8(在第二次实验中为39.3)在水溶液中(固体含量为5％)测出NTU值为2.1。残留的单体值，对N-乙烯基吡咯烷酮，为150ppm，对醋酸乙烯酯少于50ppm。对比例2
具有正常K值的于异丙醇溶液中的60％(重量)N-乙烯基吡咯烷酮和40％(重量)醋酸乙烯酯共聚物。
首先制备下列溶液
1.单体进料，由750g N-乙烯基吡咯烷酮，600g醋酸乙烯酯和800g异丙醇。
2.引发剂进料，由4g叔丁基过氧化新戊酸酯溶于100g乙醇组成。
首先量取200g单体进料和10g引发剂进料放入搅拌的实验釜中，使氮气压达1.5巴并把混合物加热到内部温度为70℃，后面的工艺类似实施例2。
得到浅白色粉末，产品K值(用1％浓度乙醇溶液)为31.7，在水溶液中(5％固体含量)测出NTU值为1.9。残留单体，对N-乙烯基吡咯烷酮，值为150ppm，对醋酸乙烯酯少于50ppm。实施例3：
具有高K值的，于乙醇溶液中的50％(重量)N-乙烯基吡咯烷酮和50％(重量)丙烯酸叔丁酯。
首先制备下列溶液：
1，单体进料，由675g N-乙烯基吡咯烷酮，750g丙烯酸叔丁酯，5g1，4-丁二醇二甲基丙烯酸酯和500g乙醇
2.引发剂进料，由4g 2.2偶氮双(2-甲基-丁腈溶于150g乙醇中组成。
首先量取混合物，由75g N-乙烯基吡咯烷酮，75g乙醇和15g引发剂进料组成，加入搅拌的实验釜中，使氮气压达1.5巴及加热混合物使内部温度达80℃。聚合反应引发后，可检测到粘度的增加和放热反应单体进料和引发剂进料是同时启动。引发剂进料在8小时内以恒定速率加入，单体进料在6小时内恒定速率加入。为了消除残留单体，80℃内部温度再保持1小时，此后量入于825g乙醇中的9g二叔丁基过氧化物溶液并关闭的反应釜在140℃加热8小时。
产生的透明的，无色和粘稠溶液的固体含量为51.3％，产物的K值(用1％浓度乙醇溶液测量)为38.3及获得了用乙醇稀释溶液使固体含量为5％时NTU值为1.0的溶液。残留单体值对N-乙烯基吡咯烷酮和对丙烯酸叔丁酯来说都小于50ppm。对比例3
具有正常K值的在乙醇溶液中的50％(重量)N-乙烯基吡咯烷酮和50％(重量)丙烯酸叔丁酯。
首先制备下列溶液：
1.单体进料，由675g N-乙烯基吡咯烷酮，750g丙烯酸叔丁酯和500g乙醇。
2.引发剂进料，由4g溶于150g乙醇中的2，2-偶氮双(2-甲基-丁腈)构成的溶液。
起始量取的混合物由75g N-乙烯基吡咯烷酮，75g乙醇和15g引发剂进料组成被加到搅拌的实验釜中，使氮气压达到1.5巴，把混合物加热到使其内部温度为80℃。其后的工艺类似实施例3。
产生的透明的，无色和粘稠溶液的固体含量为50.6％，产物的K值(用在1％浓度乙醇中的溶液测量)为30.7和获得了用乙醇稀释溶液使固体含量为5％时NTU值为0.9的溶液。残留单体值，对N-乙烯基吡咯烷酮和丙烯酸叔丁酯都小于50ppm。
Claims (7)
1.一种K值为30-50的共聚物：它是由：
A)15-84.99％(重量)至少一种选自N-乙烯基吡咯烷酮，N-乙烯基己内酰胺和N-乙烯基咪唑的单体，
B)15-84.99％(重量)还能进行游离基共聚反应的单烯属不饱和单体和
C)0.01-2％(重量)至少一种能进行游离基共聚合并具有至少二个非共轭烯属双键的单体在醇溶液中进行游离基溶液聚合获得
2.根据权利要求1的共聚物，其含如单体A)的N-乙烯基吡咯酮或N-乙烯基己内酰胺。
3.根据权利要求1或2的共聚物，含如单体B)的至少一种选自饱和的C2-C10-单羧酸的乙烯基酯，丙烯酸或甲基丙烯酸的C1-C10-烷基酯、甲基丙烯酸的N，N-二甲基氨基乙基酯及丙烯酰胺基-2-甲基丙磺酸钠盐。
4.根据权利要求1-3中任何一个权利要求的共聚物制备方法，
其中在形成游离基化合物存在下，在醇溶液中由溶液聚合聚合
A)15-84.99％(重量)一种或多种杂环N-乙烯基化合物
B)15-84.99％(重量)另外单烯属不饱和单体和
C)0.01-2％(重量)能进行游离基聚合并具有至少两个非共轭烯属双键的单体的单体混合物
5.根据权利要求1-3中任何一个权利要求的共聚物作为成膜剂的应用。
6.根据权利要求5的应用，其中成膜剂是用于头发化妆品配方中。
7.一种头发化妆品的配方，它含有权利要求1-3中任何一个权利要求中作为成膜剂的共聚物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4438706A DE4438706A1 (de) | 1994-10-29 | 1994-10-29 | Lösliche Copolymerisate für die Haarkosmetik |
| JPP4438706.7 | 1994-10-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1145371A true CN1145371A (zh) | 1997-03-19 |
| CN1087311C CN1087311C (zh) | 2002-07-10 |
Family
ID=6532020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95120363A Expired - Fee Related CN1087311C (zh) | 1994-10-29 | 1995-10-28 | 头发化妆品用的可溶性共聚物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5635169A (zh) |
| EP (1) | EP0709411B1 (zh) |
| JP (1) | JPH08231649A (zh) |
| KR (1) | KR960016618A (zh) |
| CN (1) | CN1087311C (zh) |
| CA (1) | CA2161576A1 (zh) |
| DE (2) | DE4438706A1 (zh) |
| ES (1) | ES2117344T3 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101955566A (zh) * | 2010-09-15 | 2011-01-26 | 广州大学 | 一种三元两性离子型发用定型聚合物及其制备方法 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19519339A1 (de) * | 1995-05-26 | 1996-11-28 | Basf Ag | Wasserlösliche Copolymerisate, die Vernetzer einpolymerisiert enthalten, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19719187A1 (de) * | 1997-05-07 | 1998-11-12 | Basf Ag | Verwendung von Copolymerisaten des N-Vinyl-pyrrolidons in Zubereitungen wasserunlöslicher Stoffe |
| DE19838851A1 (de) * | 1998-08-26 | 2000-03-02 | Basf Ag | Kosmetisches Mittel |
| AU5002300A (en) * | 1999-07-07 | 2001-01-30 | Isp Investments Inc. | Crosslinked cationic microgels, process for making same and hair care compositions therewith |
| DE10008263A1 (de) * | 2000-02-23 | 2001-08-30 | Basf Ag | Kosmetisches Mittel |
| DE10245586A1 (de) * | 2002-09-27 | 2004-04-08 | Basf Ag | Verwendung von Polymerisaten auf Basis von N-Vinylcaprolactam |
| DE10357532A1 (de) * | 2003-12-08 | 2005-07-07 | Basf Ag | Verwendung von Polymerisaten auf Basis von N-Vinylcaprolactam für die Haarkosmetik |
| DE112005002719B4 (de) * | 2004-11-05 | 2022-03-03 | Nippon Shokubai Co. Ltd. | Herstellung einer Vinylpyrrolidonpolymerlösung |
| WO2006049256A1 (ja) * | 2004-11-05 | 2006-05-11 | Nippon Shokubai Co., Ltd. | ビニルピロリドン／酢酸ビニル共重合体、その製造方法及びその用途 |
| JP2006169507A (ja) * | 2004-11-19 | 2006-06-29 | Lion Corp | ビニルピロリドン重合体、及びその製造方法 |
| US8030260B2 (en) | 2005-03-25 | 2011-10-04 | Chemsil Silicones, Inc | Pre-shave compositions and methods of using same |
| US7405186B2 (en) | 2005-03-25 | 2008-07-29 | Chemsil Silicones, Inc. | Lubricant compositions, condom products and methods of making same |
| DE102006021200A1 (de) * | 2006-05-06 | 2007-11-15 | Byk-Chemie Gmbh | Verwendung von Copolymeren als Haftvermittler in Lacken |
| US20110263786A1 (en) * | 2008-12-19 | 2011-10-27 | Maximilian Angel | Method for producing n-vinyl pyrrolidone/vinyl acetate copolymers |
| US9163102B2 (en) * | 2011-12-01 | 2015-10-20 | Isp Investments Inc. | Soluble branched polymers |
| BR112015021530A2 (pt) * | 2013-03-08 | 2017-07-18 | Lubrizol Advanced Mat Inc | composição para cuidados pessoais, e, método para mitigar a perda de silicone depositado |
| BR112015021509A2 (pt) * | 2013-03-08 | 2017-07-18 | Lubrizol Advanced Mat Inc | usos de pelo menos um tensoativo aniônico e de um polímero de dispersão não iônico anfifílico |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2814287A1 (de) * | 1978-04-03 | 1979-10-11 | Henkel Kgaa | Waschmittel mit einem gehalt an verfaerbungsinhibierenden zusaetzen |
| DE3312668A1 (de) * | 1983-04-08 | 1984-10-11 | Basf Ag, 6700 Ludwigshafen | Wasserloesliche polymere mit geringer hygroskopie |
| DE3627969A1 (de) * | 1986-08-18 | 1988-02-25 | Basf Ag | Copolymerisate, ihre verwendung als haarfixiermittel und diese enthaltende haarfixiermittel |
| DE3627970A1 (de) * | 1986-08-18 | 1988-02-25 | Basf Ag | Terpolymerisate, ihre verwendung in haarbehandlungsmitteln und diese enthaltende haarbehandlungsmittel |
| DE4013872A1 (de) * | 1990-04-30 | 1991-10-31 | Basf Ag | Haarfestigungs- und haarpflegemittel |
| WO1992007011A1 (en) * | 1990-10-18 | 1992-04-30 | Isp Investments Inc. | Swellable, crosslinked polyvinylpyrrolidone and cosmetic compositions therewith |
| US5139770A (en) * | 1990-12-17 | 1992-08-18 | Isp Investments Inc. | Cosmetic compositions containing strongly swellable, moderately crosslinked polyvinylpyrrolidone |
| DE4139963A1 (de) * | 1991-12-04 | 1993-06-09 | Basf Ag, 6700 Ludwigshafen, De | Redispergierbares dispersionspulver aus n-vinylpyrrolidon-vinylacetat-copolymerisat, dessen herstellung und verwendung |
| US5321110A (en) * | 1992-06-29 | 1994-06-14 | Isp Investments Inc. | Cationic polymer compositions |
| US5354823A (en) * | 1993-08-09 | 1994-10-11 | Isp Investments Inc. | Films and extrusions of cured crosslinked vinyl lactam polymer and method of preparation |
-
1994
- 1994-10-29 DE DE4438706A patent/DE4438706A1/de not_active Withdrawn
-
1995
- 1995-10-20 ES ES95116525T patent/ES2117344T3/es not_active Expired - Lifetime
- 1995-10-20 EP EP95116525A patent/EP0709411B1/de not_active Expired - Lifetime
- 1995-10-20 DE DE59502580T patent/DE59502580D1/de not_active Expired - Lifetime
- 1995-10-26 US US08/548,726 patent/US5635169A/en not_active Expired - Fee Related
- 1995-10-27 JP JP7280750A patent/JPH08231649A/ja not_active Ceased
- 1995-10-27 KR KR1019950037491A patent/KR960016618A/ko not_active Application Discontinuation
- 1995-10-27 CA CA002161576A patent/CA2161576A1/en not_active Abandoned
- 1995-10-28 CN CN95120363A patent/CN1087311C/zh not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101955566A (zh) * | 2010-09-15 | 2011-01-26 | 广州大学 | 一种三元两性离子型发用定型聚合物及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0709411B1 (de) | 1998-06-17 |
| CN1087311C (zh) | 2002-07-10 |
| JPH08231649A (ja) | 1996-09-10 |
| ES2117344T3 (es) | 1998-08-01 |
| DE4438706A1 (de) | 1996-05-02 |
| EP0709411A2 (de) | 1996-05-01 |
| EP0709411A3 (de) | 1996-09-11 |
| CA2161576A1 (en) | 1996-04-30 |
| US5635169A (en) | 1997-06-03 |
| DE59502580D1 (de) | 1998-07-23 |
| KR960016618A (ko) | 1996-05-22 |
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