JPS6213365B2 - - Google Patents
Info
- Publication number
- JPS6213365B2 JPS6213365B2 JP3820077A JP3820077A JPS6213365B2 JP S6213365 B2 JPS6213365 B2 JP S6213365B2 JP 3820077 A JP3820077 A JP 3820077A JP 3820077 A JP3820077 A JP 3820077A JP S6213365 B2 JPS6213365 B2 JP S6213365B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen atom
- weight
- methyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 229920001577 copolymer Polymers 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000006210 lotion Substances 0.000 claims description 12
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
- 239000002537 cosmetic Substances 0.000 claims description 10
- -1 ethylpropyl Chemical group 0.000 claims description 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 claims description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N butyl vinyl ether Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003581 cosmetic carrier Substances 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N vinyl ethyl ether Natural products CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 3
- FONWXYJNYDZEEY-UPHRSURJSA-N (z)-4-(hydroxymethylamino)-4-oxobut-2-enoic acid Chemical compound OCNC(=O)\C=C/C(O)=O FONWXYJNYDZEEY-UPHRSURJSA-N 0.000 claims description 2
- YLYDRLOKLHJOQR-UPHRSURJSA-N (z)-n'-(hydroxymethyl)but-2-enediamide Chemical compound NC(=O)\C=C/C(=O)NCO YLYDRLOKLHJOQR-UPHRSURJSA-N 0.000 claims description 2
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 claims description 2
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 claims description 2
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 claims description 2
- JRXNBYBCTNEZQY-UHFFFAOYSA-N 4-amino-2-methylidene-4-oxobutanoic acid Chemical compound NC(=O)CC(=C)C(O)=O JRXNBYBCTNEZQY-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 125000002704 decyl 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([H])([H])* 0.000 claims description 2
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 claims description 2
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 claims description 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims description 2
- 125000003438 dodecyl 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([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- BEBSSWYECUCQHK-UHFFFAOYSA-N ethenyl 2,2,4,4-tetramethylpentanoate Chemical compound CC(C)(C)CC(C)(C)C(=O)OC=C BEBSSWYECUCQHK-UHFFFAOYSA-N 0.000 claims description 2
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 claims description 2
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 2
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 claims description 2
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 claims description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- JJMMMVNPLDAQKX-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(C)(CO)CO JJMMMVNPLDAQKX-UHFFFAOYSA-N 0.000 claims description 2
- YZMLNCLAHHYCMY-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)prop-2-enamide Chemical compound OCC(C)(CO)NC(=O)C=C YZMLNCLAHHYCMY-UHFFFAOYSA-N 0.000 claims description 2
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 claims description 2
- VYHUMZYFJVMWRC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methylprop-2-enamide Chemical compound OCCN(C)C(=O)C=C VYHUMZYFJVMWRC-UHFFFAOYSA-N 0.000 claims description 2
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 claims description 2
- MSLHRSMWXQOHNA-UHFFFAOYSA-N n-(3-hydroxybutyl)-2-methylprop-2-enamide Chemical compound CC(O)CCNC(=O)C(C)=C MSLHRSMWXQOHNA-UHFFFAOYSA-N 0.000 claims description 2
- YXMYPOYILIWOID-UHFFFAOYSA-N n-(3-hydroxybutyl)prop-2-enamide Chemical compound CC(O)CCNC(=O)C=C YXMYPOYILIWOID-UHFFFAOYSA-N 0.000 claims description 2
- TVDRFWWLJYRVMV-UHFFFAOYSA-N n-(4-hydroxybutyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCCO TVDRFWWLJYRVMV-UHFFFAOYSA-N 0.000 claims description 2
- YBWQZBVPWXXJKQ-UHFFFAOYSA-N n-(4-hydroxybutyl)prop-2-enamide Chemical compound OCCCCNC(=O)C=C YBWQZBVPWXXJKQ-UHFFFAOYSA-N 0.000 claims description 2
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims description 2
- PQWVIUSCFLEBHJ-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(CO)(CO)CO PQWVIUSCFLEBHJ-UHFFFAOYSA-N 0.000 claims description 2
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 2
- AWDYCSUWSUENQK-UHFFFAOYSA-N n-decylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C=C AWDYCSUWSUENQK-UHFFFAOYSA-N 0.000 claims description 2
- XQPVIMDDIXCFFS-UHFFFAOYSA-N n-dodecylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C=C XQPVIMDDIXCFFS-UHFFFAOYSA-N 0.000 claims description 2
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 239000003380 propellant Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- FEFOGDISXZOUHQ-UPHRSURJSA-N (z)-n',n'-bis(hydroxymethyl)but-2-enediamide Chemical compound NC(=O)\C=C/C(=O)N(CO)CO FEFOGDISXZOUHQ-UPHRSURJSA-N 0.000 claims 1
- XSCRXCDDATUDLB-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCC(=C)C(N)=O XSCRXCDDATUDLB-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- WAORCPLTCCGKJQ-UHFFFAOYSA-N ethenyl 2,3-dimethyl-2-propan-2-ylbutanoate Chemical compound CC(C)C(C)(C(C)C)C(=O)OC=C WAORCPLTCCGKJQ-UHFFFAOYSA-N 0.000 claims 1
- IZXVGFKREHZRQK-UHFFFAOYSA-N ethenyl 4,4-dimethylpentanoate Chemical compound CC(C)(C)CCC(=O)OC=C IZXVGFKREHZRQK-UHFFFAOYSA-N 0.000 claims 1
- KJWDFJXMZXZWTC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n,2-dimethylprop-2-enamide Chemical compound OCCN(C)C(=O)C(C)=C KJWDFJXMZXZWTC-UHFFFAOYSA-N 0.000 claims 1
- UGHVZLXVTYMJBC-UHFFFAOYSA-N n-(2-methylbutan-2-yl)prop-2-enamide Chemical compound CCC(C)(C)NC(=O)C=C UGHVZLXVTYMJBC-UHFFFAOYSA-N 0.000 claims 1
- XAYXLWICCULIEB-UHFFFAOYSA-N n-(2-methylhexan-2-yl)prop-2-enamide Chemical compound CCCCC(C)(C)NC(=O)C=C XAYXLWICCULIEB-UHFFFAOYSA-N 0.000 claims 1
- ZTYYOTXHQDVQDY-UHFFFAOYSA-N n-(2-methylpentan-2-yl)prop-2-enamide Chemical compound CCCC(C)(C)NC(=O)C=C ZTYYOTXHQDVQDY-UHFFFAOYSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000005956 quaternization reaction Methods 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 239000004922 lacquer Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
- QFAQTCIEPLTZOF-UHFFFAOYSA-N 4-(hydroxymethylamino)-2-methylidene-4-oxobutanoic acid Chemical compound OCNC(=O)CC(=C)C(O)=O QFAQTCIEPLTZOF-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N ethylmethylbenzene Natural products CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- 229960001730 nitrous oxide Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
Classifications
-
- 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
- A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- 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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Cosmetics (AREA)
Description
本発明はＮ―アルキル・アクリルアミド又はメ
タクリルアミドに基く新規なターポリマー及び高
級ポリマー及びそれらの化粧料、とくにラツカー
及びセツテイングローシヨンへの応用を目的とす
る。
本発明はまたこれら新規なコポリマーの製法も
目的とする。
多数の合成ポリマーがラツカー又はセツテイン
グローシヨンに使用するためすでに提案されてい
る。
本発明者は、今般、一群の新規なコポリマーに
より優れたラツカー及びセツテイングローシヨン
を製造できることを認めた。
本発明によるこれらのポリマーを使用すること
により、従来使用されたものと異なりラツカー及
びセツテイングローシヨンに優れた性質を付与
し、調髪の持続性をよくすることが可能になる。
従つて本発明は、下記(a)(b)及び(c)のモノマーの
それぞれの少なくとも１種を共重合させて得られ
新規なコポリマーとくにターポリマーを提供する
ことを目的とする：
(a) 式（）：
のモノマー（ただし、式中のＲは炭素原子数１
ないし10の直鎖の又は分岐鎖アルキル基、
R1，R2及びR3は水素原子又はメチル基を表わ
しｎは０又は１でありｎが１のときＸは酸素原
子を表わす）、
(b) 式（）
のモノマー（ただし、式中のｍは０又は１であ
りｍが０の場合にはR4は水素原子又は―
COOH基、R5は水素原子又は―CH3基であり、
ｍが１の場合にはR4は水素原子、R5は―
COOH基である）
(c) スチレン、Ｎ―ビニルピロリドン及び下記(i)
ないし(vi)の式のモノマーからなるグループから
選ばれたモノマー；
（ただし式中のR6は水素原子又はメチル基を
表わす）、
（ただし式中のR7は水素原子又はメチル基を
表わし、R8は炭素原子数１ないし18の直鎖又は
分岐鎖アルキル基、第四級化されているか又は第
四級化されていない―（CH3）2―Ｎ（CH3）2基、
―CH2―CH2―OH基、
The present invention is directed to new terpolymers and higher polymers based on N-alkyl acrylamides or methacrylamides and their application in cosmetics, in particular in lacquers and setting lotions. The present invention is also directed to methods of making these new copolymers. A number of synthetic polymers have already been proposed for use in lacquers or setting lotions. The inventors have now recognized that superior lacquers and setting lotions can be made with a new family of copolymers. The use of these polymers according to the invention makes it possible to impart superior properties to lacquers and setting lotions, unlike those previously used, and to improve the durability of hair styling. Therefore, it is an object of the present invention to provide a novel copolymer, in particular a terpolymer, obtained by copolymerizing at least one of the following monomers (a), (b) and (c): (a) formula(): monomer (in the formula, R has 1 carbon atom)
to 10 straight-chain or branched alkyl groups,
R 1 , R 2 and R 3 represent a hydrogen atom or a methyl group, n is 0 or 1, and when n is 1, X represents an oxygen atom), (b) Formula () monomer (however, m in the formula is 0 or 1, and when m is 0, R 4 is a hydrogen atom or -
COOH group, R 5 is a hydrogen atom or -CH 3 group,
When m is 1, R 4 is a hydrogen atom, R 5 is -
COOH group) (c) Styrene, N-vinylpyrrolidone and the following (i)
A monomer selected from the group consisting of monomers of formulas (vi) to (vi); (However, R 6 in the formula represents a hydrogen atom or a methyl group), (However, R 7 in the formula represents a hydrogen atom or a methyl group, and R 8 represents a straight or branched alkyl group having 1 to 18 carbon atoms, quaternized or non-quaternized. (CH 3 ) 2 —N(CH 3 ) 2 groups,
-CH 2 -CH 2 -OH group,
【式】
基及び―（CH2―CH2―Ｏ）l―R′基を表わしR′は
メチル基又はエチル基を表わしｌは３又は12であ
る）、
（ただしR9は炭素原子数１ないし16の直鎖又
は分岐鎖アルキル基を表わす）、
（ただしR″は炭素原子数１ないし３のアルキ
ル基を表わす）、
(v) CH2＝CH―Ｏ―R10 ……（）
（ただしR10は炭素原子数１ないし17の直鎖又
は分岐鎖飽和アルキル基を表わす）、
（ただしR11は水素原子又はメチル基を表わ
し、Ｚは炭素原子数１ないし６の直鎖又は分岐鎖
アルキレン基であつて１個又は２個のヒドロキシ
メチル官能基により置換された、又は置換されて
いないものを表わし、ｐは０又は１であり、ｐが
０ならばR13は水素原子又は―COR14基であり、
R14は―OH又は―NH―R15基でありR15は水素原
子又はＺ―OH基でありR12は水素原子又は―CH3
基であり、ｐが１ならばR13は水素原子、R12は―
COR14基でR14は上記のものと同じ意味である）。
上記の式（）においてはＺ基は望ましくは―
CH2―、―（CH2）2―、―CH（C2H5）―CH2―、
―Ｃ（CH3）2―CH2―、―Ｃ（CH2OH）2―CH2
―、―Ｃ（CH3）2―CH2―CH（CH3）―及び―Ｃ
（CH3）（CH2OH）―CH2―からなる群から選ば
れる。
前記したとおり、本発明によるコポリマーはタ
ーポリマーであることが好ましい。しかしながら
―変法によると、コポリマーはテトラポリマー、
ペンタポリマ又は高級ポリマとすることができ
る。
この場合、コポリマーは式（）のモノマー１
種以上及び／又は式（）のモノマー１種以上及
び／又はまた上記式（）ないし（）により表
わされるモノマー１種以上を共重合することによ
り得られる。
本発明によるコポリマーは下記の一般式により
表わすことができる：
（ただしR1，R2，R3，R4及びR5の基、ｎ，ｍ
及びＸは、式（）及び（）において述べたも
のと同一の意義を有し、ｗは５ないし90重量％
に、ｘは５ないし90重量％に、ｙは５ないし60重
量％に相当し、Ｍはスチレン、Ｎ―ビニル・ピロ
リドン又は前記の式（）ないし（）の不飽和
モノマーから誘導された下記(i)〜(viii)の反復単位の
少なくとも一つを表わす：
上記式中のR6，R7，R8，R9，R10，R11，R12，
R13，R″，ｐおよびＺは前記式（）〜（）に
おけると同一の意義を有する）。
式（）のモノマーとしては、Ｎ―第三級ブチ
ルアクリルアミド、Ｎ―オクチル・アクリルアミ
ド、Ｎ―デシルアクリルアミド、Ｎ―ドデシル・
アクリルアミド、Ｎ―〔１，１―ジメチル）―１
―プロピル〕アクリルアミド、Ｎ―〔１，１ジメ
チル）―１―ブチル〕アクリルアミド、Ｎ―
〔１，１―ジメチル）―１―ペンチル〕アクリル
アミド、Ｎ―イソプトキシメチルアクリルアミド
ならびに対応するメタクリルアミドをとくにあげ
ることができる。
式（）のモノマーとしては、アクリルアミ
ド、メタクリルアミド、マレアミド酸及びイタコ
ンアミド酸をとくにあげることができる。
式（）ないし（）のモノマーとしては、ア
クリロニトリル、メタクリロニトリル、メチル
―、エチル―、プロピル―、イソプロピル―、ブ
チル―、第三級ブチル―、ヘキシル―、デシル
―、ドデシル―、オクタデシル―、２―ヒドロキ
シ・エチル―、第四化合物の型の又は他の型の２
―Ｎ・Ｎ―ジメチルアミノーエチル―及びω―メ
チル―又はエチル・ポリエチレン・グリコールー
のアクリレート及びメタクリレート、酢酸ビニ
ル、プロピオン酸ビニル、酪酸ビニル、ラウリン
酸ビニル、ステアリン酸ビニル、ピバリン酸ビニ
ル、ネオヘプタノン酸ビニル、ネオクタノン酸ビ
ニル、ネオデカノン酸ビニル、２，２，４，４テ
トラメチル吉草酸ビニル、２―イソプロピル―
２，３―ジメチル酪酸ビニル、マレイン酸ジメチ
ル、マレイン酸ジエチル、イタコン酸ジメチル、
イタコン酸ジエチル、メチルビニルエーテル、エ
チルビニルエーテル、ブチルビニルエーテル、イ
ソプロピルビニルエーテル、オクチルビニルエー
テル、ドデシルビニルエーテル、オクタデシルビ
ニルエーテル、Ｎ―ヒドロキシメチルアクリルア
ミド、Ｎヒドロキシメチルメタクリルアミド、Ｎ
―〔（２―ヒドロキシ）―エチル〕アクリルアミ
ド、Ｎ―〔（２―ヒドロキシ）エチル〕メタクリ
ルアミド、Ｎ―ヒドロキシメチルマレアミド酸、
Ｎ―ヒドロキシメチルマレアミド、Ｎ，Ｎジヒド
ロキシメチルマレアミド、Ｎ―ヒドロキシメチル
イタコンアミド酸、Ｎ―〔（１―ヒドロキシメチ
ル）―プロピル〕アクリルアミド、Ｎ―〔（１―
ヒドロキシメチル）―プロピル〕メタクリルアミ
ド、Ｎ―〔（１―メチル―１―ヒドロキシメチ
ル）―１―エチル〕アクリルアミド、Ｎ―〔（１
―メチル―１―ヒドロキシメチル）―１―エチ
ル〕メタクリルアミド、Ｎ―〔１，１，１―トリ
ス（ヒドロキシメチル）メチル〕アクリルアミ
ド、Ｎ―〔１，１，１―トリス（ヒドロキシメチ
ル）―メチル〕メタクリルアミド、Ｎ―〔（３―
ヒドロキシ―１，１―ジメチル）―ブチル〕アク
リルアミド、Ｎ―〔（３―ヒドロキシ―１，１―
ジメチル）ブチル〕メタクリルアミド、Ｎ―
〔（２―ヒドロキシ）エチル〕―Ｎ―メチルアクリ
ルアミド、Ｎ―〔（２―ヒドロキシ）エチル〕―
Ｎ―メチルメタクリルアミド、Ｎ―〔１，１―ビ
ス（ヒドロキシメチル〕エチル〕アクリルアミド
及びＮ―〔１，１―ビス（ヒドロキシメチル）エ
チル〕メタクリルアミドをとくにあげることがで
きる。
本発明によるコポリマーは1000ないし500000の
分子量、とくに2000ないし200000の分子量であ
る、ことが好ましい。
R4基が遊離の官能カルボキシル酸である特殊
な実施形式においては、この基はモノエタノール
アミン、ジエタノールアミン、トリエタノールア
ミン、トリイソプロパノールアミンなどのイソプ
ロパノールアミン類、モルホリンならびに２―ア
ミノ―２―メチル―プロパノール及び２―アミノ
―２―メチル―１，３―プロパンジオールなど若
干のアミノアルコールなどの有機塩基を少なくと
も１種用いて中和することができる。
カルボキシル官能基はこれらの有機塩基を10な
いし150％の比率で用いて中和することができ
る。
本発明はまた上述のコポリマーの製法も目的と
するものである。
これらのコポリマーはアルコール類、ケトン、
エステル又は炭化水素などの有機溶媒中で溶液重
合により共重合させて調製し得る。
これらの溶媒としてはメタノール、エタノー
ル、イソプロパノール、酢酸エチル、エチルメチ
ルケトン、ベンゼンなどをとくにあげることがで
きる。
共重合はまた水など不活性の溶媒中で懸濁又は
乳濁重合により行なうこともできる。
共重合はまた塊状重合により行なうこともでき
る。
これらの共重合は、過酸化ベンゾイル、過酸化
ラウロイル、アゾビスイソブチロニトリル、過酸
化水素、（NH4）4S2O8、FeClなど各種酸化還元系
触媒などの遊離基を生じる重合触媒の存在におい
て行なうことができる。
触媒の濃度は所望のコポリマーの分子量に応じ
て、反応させるモノマに対して0.2ないし10重量
％の範囲で変動する。
本発明はそのほか上述の新規コポリマーを化粧
料組成物に利用することを目的とする。
本発明はとくにラツカー又はセツテイングロー
シヨンの形の化粧料組成物を目的とする。
これらの化粧料組成物は本質的には前記したコ
ポリマーを少なくとも１種、適宜な化粧料担体に
溶液として含むことを特徴とする。
本発明による化粧料担体はたとえば、場合によ
りエアロゾルの形の毛髪用ラツカー、セツテイン
グローシヨン、毛髪処理組成物、展色剤、シヤン
プー又はシヤンプで洗髪した后で適用するリンス
とすることができる。
例えば毛髪用ラツカーエーロゾルは、本発明に
よるコポリマー0.2ないし８重量％、６ないし30
重量％、好ましくは８ないし25重量％のアルコー
ル、残部はほぼジクロロジフルオロメタン、トリ
クロロフルオロメタン、酸化二窒素又は二酸化炭
素又はこれらの混合物などの加圧液化噴射用ガス
からなるものを、エアロゾル噴射容器に収容して
調製することができる。
この種のアルコールとしてはエタノール又はイ
ソプロパノールを用いることが好ましい。
本発明によるセツテイングローシヨンは、たと
えばアルコール含有量20ないし66％の水性アルコ
ール溶液に、本発明によるコポリマー0.3ないし
６重量％を導入して調製することができる。
本発明による化粧料組成物は、また香料、着色
料、防腐剤、可塑剤、カチオン界面活性剤、非イ
オン界面活性剤、光沢を改善するためのシリコー
ン、その他の化粧料用樹脂などの在来の化粧料用
補助剤を含有し得る。
本発明の理解を容易にするために以下に若干の
コポリマー製造の実施例及びこれらに基く組成物
の数例を示す。
コポリマー製造の実施例
実施例 １
冷却器、撹拌機及び窒素送入管を備えた１フ
ラスコに、
エタノール 400ｇ
Ｎ―第三ブチルアクリルアミド 50ｇ
アクリルアミド 27.5ｇ
メチルメタクリレート 17.5ｇ
アゾビイソブチロニトリル １ｇ
を装入し、反応混合物をサーモスタツトにより80
℃に８時間加熱した后室温まで放冷する。
次に、この溶液を沈澱剤として酢酸エチルを含
んでいる容器に少しずつ注ぐ。沈澱したポリマー
は続いて別し減圧乾燥する。
収量：76％
粘度：2.95cpo（５％DMF溶液として34.6℃
で）
実施例 ２
上記実施例第１に記載のものと同じ作業法によ
つて下記のものを共重合させる：
Ｎ―第三ブチルアクリルアミド 65ｇ
アクリルアミド 20ｇ
Ｎ―ヒドロキシメチルアクリルアミド 15ｇ
アゾビスイソブチロニトリル １ｇ
粘度：2.61cpo（５％DMF溶液として34.6℃
で）
その他のコポリマーの例（実施例３―17）を表
１に示した。
これらのコポリマーはすべて実施例１に従つて
調製したものであり、単に沈澱剤の性質が相違す
るだけである。[Formula] represents a group and --(CH 2 --CH 2 --O) l --R' group, R' represents a methyl group or an ethyl group, and l is 3 or 12), (However, R 9 represents a straight chain or branched alkyl group having 1 to 16 carbon atoms), (However, R″ represents an alkyl group having 1 to 3 carbon atoms), (v) CH 2 =CH―O―R 10 ... () (However, R 10 is a straight or branched chain having 1 to 17 carbon atoms. (representing a chain saturated alkyl group), (However, R 11 represents a hydrogen atom or a methyl group, and Z is a straight or branched alkylene group having 1 to 6 carbon atoms, substituted or unsubstituted with 1 or 2 hydroxymethyl functional groups. p is 0 or 1, and if p is 0, R 13 is a hydrogen atom or a -COR 14 group,
R 14 is -OH or -NH-R 15 group, R 15 is a hydrogen atom or Z-OH group, and R 12 is a hydrogen atom or -CH 3
group, and if p is 1, R 13 is a hydrogen atom, R 12 is -
COR 14 groups and R 14 has the same meaning as above). In the above formula (), the Z group is preferably -
CH 2 ―, ―(CH 2 ) 2 ―, ―CH(C 2 H 5 )―CH 2 ―,
-C(CH 3 ) 2 -CH 2 -, -C(CH 2 OH) 2 -CH 2
--, --C(CH 3 ) 2 --CH 2 --CH(CH 3 ) --and --C
Selected from the group consisting of (CH 3 )(CH 2 OH)—CH 2 —. As mentioned above, the copolymers according to the invention are preferably terpolymers. However - according to a variant, the copolymer is a tetrapolymer,
It can be a pentapolymer or a high grade polymer. In this case, the copolymer is a monomer of formula () 1
It can be obtained by copolymerizing one or more types of monomers and/or one or more monomers of the formula () and/or one or more monomers represented by the above formulas () to (). The copolymers according to the invention can be represented by the following general formula: (However, R 1 , R 2 , R 3 , R 4 and R 5 groups, n, m
and X have the same meaning as stated in formulas () and (), and w is 5 to 90% by weight
, x corresponds to 5 to 90% by weight, y corresponds to 5 to 60% by weight, M is styrene, N-vinyl pyrrolidone or the following ( represents at least one of the repeating units i) to (viii): R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 in the above formula,
R 13 , R″, p and Z have the same meanings as in the above formulas () to ()). Monomers of formula () include N-tertiary butylacrylamide, N-octyl acrylamide, N- Decyl acrylamide, N-dodecyl
Acrylamide, N-[1,1-dimethyl)-1
-propyl]acrylamide, N-[1,1 dimethyl)-1-butyl]acrylamide, N-
[1,1-dimethyl)-1-pentyl]acrylamide, N-isoptoxymethylacrylamide and the corresponding methacrylamide may be mentioned in particular. As monomers of formula (), mention may be made in particular of acrylamide, methacrylamide, maleamic acid and itaconamic acid. Monomers of formulas () to () include acrylonitrile, methacrylonitrile, methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, hexyl, decyl, dodecyl, octadecyl, 2-Hydroxy ethyl-, quaternary compound type or other type 2
-N/N-dimethylaminoethyl- and ω-methyl- or ethyl polyethylene glycol-acrylates and methacrylates, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl laurate, vinyl stearate, vinyl pivalate, neoheptanonic acid Vinyl, vinyl neoctanoate, vinyl neodecanoate, vinyl 2,2,4,4-tetramethylvalerate, 2-isopropyl-
Vinyl 2,3-dimethylbutyrate, dimethyl maleate, diethyl maleate, dimethyl itaconate,
Diethyl itaconate, methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether, isopropyl vinyl ether, octyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, N-hydroxymethylacrylamide, N-hydroxymethylmethacrylamide, N
-[(2-hydroxy)-ethyl]acrylamide, N-[(2-hydroxy)ethyl]methacrylamide, N-hydroxymethylmaleamic acid,
N-hydroxymethylmaleamide, N,N dihydroxymethylmaleamide, N-hydroxymethylitaconamic acid, N-[(1-hydroxymethyl)-propyl]acrylamide, N-[(1-
hydroxymethyl)-propyl]methacrylamide, N-[(1-methyl-1-hydroxymethyl)-1-ethyl]acrylamide, N-[(1
-Methyl-1-hydroxymethyl)-1-ethyl]methacrylamide, N-[1,1,1-tris(hydroxymethyl)methyl]acrylamide, N-[1,1,1-tris(hydroxymethyl)-methyl ]Methacrylamide, N-[(3-
Hydroxy-1,1-dimethyl)-butyl]acrylamide, N-[(3-hydroxy-1,1-
dimethyl)butyl]methacrylamide, N-
[(2-hydroxy)ethyl]-N-methylacrylamide, N-[(2-hydroxy)ethyl]-
Particular mention may be made of N-methylmethacrylamide, N-[1,1-bis(hydroxymethyl)ethyl]acrylamide and N-[1,1-bis(hydroxymethyl)ethyl]methacrylamide. Preference is given to a molecular weight of 1000 to 500000, in particular a molecular weight of 2000 to 200000. In a special embodiment in which the R 4 group is a free functional carboxylic acid, this group can be monoethanolamine, diethanolamine, triethanolamine, Using at least one organic base such as isopropanolamines such as triisopropanolamine, morpholine, and some amino alcohols such as 2-amino-2-methyl-propanol and 2-amino-2-methyl-1,3-propanediol. The carboxyl functionality can be neutralized using these organic bases in a proportion of 10 to 150%. The present invention also aims at a process for preparing the above-mentioned copolymers. Copolymers of alcohols, ketones,
It can be prepared by copolymerization by solution polymerization in organic solvents such as esters or hydrocarbons. These solvents include methanol, ethanol, isopropanol, ethyl acetate, ethyl methyl ketone, benzene and the like. Copolymerization can also be carried out by suspension or emulsion polymerization in an inert solvent such as water. Copolymerization can also be carried out by bulk polymerization. These copolymerizations are carried out using polymerization catalysts that generate free radicals, such as benzoyl peroxide, lauroyl peroxide, azobisisobutyronitrile, hydrogen peroxide, various redox catalysts such as (NH 4 ) 4 S 2 O 8 , and FeCl. It can be done in the presence of The concentration of catalyst varies from 0.2 to 10% by weight, based on the monomers to be reacted, depending on the molecular weight of the desired copolymer. Another object of the present invention is to utilize the above-mentioned novel copolymers in cosmetic compositions. The present invention is particularly directed to cosmetic compositions in the form of lacquers or setting lotions. These cosmetic compositions are essentially characterized in that they contain at least one of the aforementioned copolymers in solution in a suitable cosmetic carrier. Cosmetic carriers according to the invention can be, for example, hair lacquers, setting lotions, hair treatment compositions, color vehicles, shampoos or rinses to be applied after shampooing the hair, optionally in the form of an aerosol. For example, a Lutzker aerosol for hair contains 0.2 to 8% by weight of the copolymer according to the invention, 6 to 30% by weight of the copolymer according to the invention.
% by weight, preferably from 8 to 25% by weight of alcohol, the balance approximately consisting of a pressurized liquefied propellant gas such as dichlorodifluoromethane, trichlorofluoromethane, dinitrogen oxide or carbon dioxide or mixtures thereof. It can be prepared by storing it in As this type of alcohol, it is preferable to use ethanol or isopropanol. Setting lotions according to the invention can be prepared, for example, by incorporating 0.3 to 6% by weight of the copolymers according to the invention into an aqueous alcoholic solution with an alcohol content of 20 to 66%. The cosmetic composition according to the invention may also contain conventional ingredients such as fragrances, colorants, preservatives, plasticizers, cationic surfactants, nonionic surfactants, silicones to improve gloss, and other cosmetic resins. may contain cosmetic adjuvants. In order to facilitate an understanding of the invention, some examples of copolymer preparation and compositions based thereon are given below. Examples of copolymer production Example 1 A flask equipped with a condenser, a stirrer and a nitrogen inlet was charged with 400 g of ethanol, 50 g of N-tert-butylacrylamide, 27.5 g of acrylamide, 17.5 g of methyl methacrylate, and 1 g of azobiisobutyronitrile. and the reaction mixture was heated to 80°C by thermostat.
After heating to ℃ for 8 hours, it was allowed to cool to room temperature. This solution is then poured in portions into a container containing ethyl acetate as a precipitant. The precipitated polymer is subsequently separated and dried under reduced pressure. Yield: 76% Viscosity: 2.95cpo (34.6℃ as 5% DMF solution)
Example 2 The following are copolymerized by the same procedure as described in Example 1 above: N-tert-butylacrylamide 65 g acrylamide 20 g N-hydroxymethylacrylamide 15 g azobisisobutyronitrile 1g Viscosity: 2.61cpo (34.6℃ as 5% DMF solution)
) Examples of other copolymers (Examples 3-17) are shown in Table 1. All of these copolymers were prepared according to Example 1, differing only in the nature of the precipitant.
【表】【table】
【表】
組成物の実施例
実施例 Ａ
本発明に従つて下記の成分を混合してセツテイ
ングローシヨンを調製した：
実施例１により製造したポリマー ２ｇ
香 料 0.1ｇ
エタノール 45ｇ
水を加えて100ｇとする。
このセツテイングローシヨンを従来の方法で適
用すると、毛髪に光沢のある外貎を与え持続性が
優れていた。
この実施例においては使用した実施例１により
製造したコポリマーを実施例５，10―12及び15に
より製したコポリマー同量で代替できる。
実施例 Ｂ
本発明に従つて下記の成分を混合して毛髪用ラ
ツカを調製した；
実施例２により製造したコポリマー ４ｇ
香 料 0.3ｇ
エタノールを加えて100ｇとする。この溶液25
ｇをトリクロロフルオロメタン47ｇ、ジクロロジ
フルオロメタン28ｇとともにエーロゾル噴射容器
に収容した。
このラツカーを噴霧すると毛髪の光沢のある美
しい外貎と強力なラツカー効果とが得られた。毛
髪は手触りが滑かで、櫛又はブラシをかけると容
易にラツカーが除去された。
この実施例において使用した実施例２により製
したコポリマーを実施例４，６―８及び10により
製造したコポリマーの同量で代替できる。
実施例 Ｃ
本発明に従つて下記成分を混合して毛髪用ラツ
カエーロゾルを調製した：
実施例11により製造したポリマー ５ｇ
香 料 0.07ｇ
エタノールを加えて100ｇとする。この溶液93
ｇをエーロゾル噴射容器に収容し内圧が約８バー
ルになるように二酸化炭素ガスを導入した。
この実施例において使用した実施例11により製
造したポリマーを実施例12，14及び16により製造
したポリマーの同量で有利に代替できる。
実施例 Ｄ
本発明に従つて下記成分を混合してセツテイン
グローシヨンを調製した：
実施例９により製造したポリマー（硫酸ジメチ
ルで第四化合物としたもの） ２ｇ
香 料 0.1ｇ
イソプロパノール 45ｇ
水を加えて100ｇとした。
このセツテイングローシヨンを従来の方法で適
用すると、毛髪に光沢のある外貎と優れた持続性
とを与えることができた。実施例９によるポリマ
ーを実施例13によるポリマーを同じく第四化合物
としたものと同量で有利に代替できる。
実施例 Ｅ
本発明に従つて下記成分を混合して毛髪用ラツ
カを調製した：
実施例２により製造したポリマー ４ｇ
香 料 0.3ｇ
エタノール 100ｇ
この溶液25ｇをトリクロロフルオロメタン47ｇ
及びジクロロジフルオロメタン28ｇとともにエア
ロゾル噴射容器に収容した。
このラツカーを噴霧すると、毛髪の光沢のある
美しい外貎と強いラツカー効果とが得られた。毛
髪は手触りが滑かで、櫛又はブラシをかければ容
易にラツカーが除去できた。
この実施例においては実施例２によるポリマー
を、実施例第17によるポリマー同量で有利に代替
できる。Table Composition Examples Example A A setting lotion was prepared according to the invention by mixing the following ingredients: Polymer prepared according to Example 1 2 g Fragrance 0.1 g Ethanol 45 g Water added to 100 g shall be. When this setting lotion was applied in a conventional manner, it gave the hair a shiny outer coat and was long lasting. In this example, the copolymer prepared according to Example 1 used can be replaced with the same amount of copolymer prepared according to Examples 5, 10-12 and 15. Example B A hair lacquer was prepared according to the invention by mixing the following ingredients: 4 g copolymer prepared according to Example 2 0.3 g perfume Add ethanol to 100 g. This solution 25
g was placed in an aerosol injection container along with 47 g of trichlorofluoromethane and 28 g of dichlorodifluoromethane. When sprayed with this lacquer, a beautiful, glossy outer layer of hair and a strong lacquer effect were obtained. The hair was smooth to the touch and lacquer was easily removed by combing or brushing. The copolymers made according to Example 2 used in this example can be replaced with the same amount of copolymers made according to Examples 4, 6-8, and 10. Example C A Ratska aerosol for hair was prepared according to the invention by mixing the following ingredients: Polymer prepared according to Example 11 5 g Perfume 0.07 g Ethanol was added to make up to 100 g. This solution93
g was placed in an aerosol injection container and carbon dioxide gas was introduced so that the internal pressure was approximately 8 bar. The polymer prepared according to Example 11 used in this example can be advantageously replaced with the same amount of the polymer prepared according to Examples 12, 14 and 16. Example D A setting lotion was prepared according to the invention by mixing the following ingredients: 2 g of the polymer prepared according to Example 9 (quaternized with dimethyl sulfate) 0.1 g of perfume 45 g of isopropanol Added water It was made into 100g. When applied in a conventional manner, this setting lotion gave the hair a shiny outer coat and excellent durability. The polymer according to Example 9 can advantageously be substituted in the same amount as the polymer according to Example 13, also as the fourth compound. Example E A hair lacquer was prepared according to the invention by mixing the following ingredients: 4 g polymer prepared according to Example 2 0.3 g perfume 100 g ethanol 25 g of this solution was mixed with 47 g trichlorofluoromethane
and 28 g of dichlorodifluoromethane in an aerosol injection container. When this lacquer was sprayed, a beautiful, shiny outer layer of hair and a strong lacquer effect were obtained. The hair was smooth to the touch, and lacquer could be easily removed by combing or brushing. In this example, the polymer according to Example 2 can be advantageously replaced by the same amount of the polymer according to Example 17.
Claims (1)
岐鎖アルキル基を表わし、R1，R2及びR3は水素
原子又はメチル基を表わしｎは０又は１でありｎ
が１のときＸは酸素原子を表わす；ｍは０又は１
でありｍが０ならばR4は水素原子又は−COOH
基、R5は水素原子又は−CH3基であり、ｍが１な
らばR4は水素原子、R5は−COOH基である；Ｍ
は下記(i)〜(viii)に示される反復単位の少なくとも１
つを表わす： （ただしR6は水素原子又はメチル基を表わ
す） （ただしR7は水素原子又はメチル基を表わ
し、R8は炭素数１ないし18個の直鎖又は分岐鎖
アルキル基、第４級化されているか又は第４級化
されていない−（CH2）2−Ｎ（CH3）2基、―CH2―
CH2―OH基、【式】基及び− （CH2―CH2―Ｏ）l―R′基でかつR′がメチル基又
はエチル基を表わしｌが３又は４であるものを表
わす） （ただしR9は炭素数１ないし16個の直鎖又は
分岐鎖アルキル基を表わす）、 （ただしR″は炭素数１ないし３個のアルキル
基を表わす）、 （ただしR10は炭素数１ないし17個の直鎖又は
分岐鎖飽和アルキル基を表わす）、 （ただしR11は水素原子又はメチル基を表わ
し、Ｚは炭素数１ないし６個の直鎖又は分岐鎖ア
ルキレン基であつてかつ場合により１個又は２個
のヒドロキシメチル官能基により置換されている
ものを表わし、ｐは０又は１であり、ｐが０なら
ばR13は水素原子又は―COR14基でありR14は―
OH又は―NH―R15基であり、R15は水素原子又は
Ｚ―OH基でありR12は水素原子又は―CH3基であ
り、ｐが１ならばR13は水素原子、R12は―COR14
基であり、R14は上記のものと同じ意味を表わ
す）； ｗは５〜90重量％であり、ｘは５〜90重量％で
あり、ｙは５〜60重量％である〕で表わされる反
復単位からなり、かつ1000〜500000の分子量を有
する新規コポリマー。 ２ 分子量が2000ないし200000である特許請求の
範囲第１項に記載のコポリマー。 ３ ａ 式（）： （式中、Ｒは炭素数１ないし10個の直鎖又は
分岐鎖アルキル基を表わし、R1，R2及びR3は
水素原子又はメチル基を表わしｎは０又は１で
ありｎが１のときＸは酸素原子を表わす）のモ
ノマーの少なくとも１種； ｂ 式（）： （式中、ｍは０又は１でありｍが０ならば
R4は水素原子又は―COOH基、R5は水素原子
又は―CH3基であり、ｍが１ならばR4は水素原
子、R5は―COOH基である）のモノマーの少
なくとも１種；および、 ｃ スチレン、Ｎ―ビニルピロリドン及び下記(i)
ないし(vi)の式のモノマーからなる群から選ばれ
たモノマーの少なくとも１種、 （ただしR6は水素原子又はメチル基を表わ す） （ただしR7は水素原子又はメチル基を表わ
し、R8は炭素数１ないし18個の直鎖又は分岐
鎖アルキル基、第四級化されているか又は第４
級化されていない―（CH2）2―Ｎ（CH3）2基、
―CH2―CH2―OH基、
【式】基及び―（CH2―CH2 ―Ｏ）l―R′基であつてR′がメチル基又はエチル基
を表わしｌは３又は４であるものを表わす） （ただしR9は炭素数１ないし16個の直鎖又
は分岐鎖アルキル基を表わす）、 （ただしR″は炭素数１ないし３個のアルキ
ル基を表わす）、 （） CH2＝CH―Ｏ―R10 ……（） （ただしR10は炭素数１ないし17個の直鎖又
は分岐鎖飽和アルキル基を表わす）、 （ただしR11は水素原子又はメチル基を表わ
し、Ｚは炭素数１ないし６個の直鎖又は分岐鎖
アルキレン基であつてかつ場合により１個又は
２個のヒドロキシメチル官能基により置換され
ているものを表わし、ｐは０又は１であり、ｐ
が０ならばR13は水素原子又は―COR14基であ
りR14は―OH又は―NH―R15基でありR15は水
素原子又はＺ―OH基でありR12は水素原子又は
―CH3基であり、ｐが１ならばR13は水素原
子、R12は―COR14基で、R14は上記のものと同
じ意味を表わす）；を遊離基を生ずる重合触媒
の存在下において塊状重合するかまたは適当な
溶剤中で溶液重合することを特徴とする、一般
式： （ただし、式中のR1，R2，R3，R4及びR5の
基、ｎ，ｍ及びＸは前記と同一意義を有するも
のであり、Ｍは下記(i)〜(viii)で示される反復単位
の少なくとも１つを表わす； （上記式中、R6，R7，R8，R9，R10，R11，
R12，R13，R″，ｐおよびＺは前記の意義を有
する）；ｗは５ないし90重量％であり、ｘは５
ないし90重量％であり、ｙは５ないし60重量％
である）で表わされる反復単位からなり、かつ
1000〜500000の分子量を有する新規コポリマー
の製造方法。 ４ 式（）のモノマーの少なくとも１種５ない
し90重量％、式（）のモノマーの少なくとも１
種５ないし90重量％及びスチレン、Ｎ―ビニルピ
ロリドン又は式（）ないし（）のモノマーの
少なくとも１種５ないし60重量％を共重合させる
特許請求の範囲第３項記載の方法。 ５ 式（）のモノマはＮ―第三ブチル、アクリ
ルアミド、Ｎ―オクチル アクリルアミド、Ｎ―
デシル―アクリルアミド、Ｎ―ドデシルアクリル
アミド、Ｎ―〔１，１ジメチル―１―プロピル〕
アクリルアミド、Ｎ―〔（１，１ジメチル）―１
―ブチル〕アクリルアミド、Ｎ―〔（１，１―ジ
メチル）―１―ペンチル〕アクリルアミド、Ｎ―
イソブトキシメチルアクリルアミド及び対応する
メタクリルアミドからなる群から選ばれる特許請
求の範囲第３項又は第４項記載の方法。 ６ 式（）のモノマはアクリルアミド、メタク
リルアミド、マレアミド酸及びイタコンアミド酸
からなる群から選ばれる特許請求の範囲第３項又
は第４項記載の方法。 ７ 式（）ないし（）のモノマはアクリロニ
トリル、メタクリロニトリル、メチル―、エチル
―プロピル―、イソプロピル―、ブチル―、第三
ブチル―、ヘキシル―、デシル―、ドデシル―、
オクタデシル―、２―ヒドロキシ―エチル―、第
四級化されているか又はされていない２―Ｎ，Ｎ
ジメチルアミノ―エチル―、及びω―メチル又は
エチルポリエチレングリコール―のアクリレート
及びメタクリレート、酢酸ビニル、プロピオン酸
ビニル、酪酸ビニル、ラウリン酸ビニル、ステア
リン酸ビニル、ピバル酸ビニル、ネオヘプタノン
酸ビニル、ネオクタノン酸ビニル、ネオデカノン
酸ビニル、２，２，４，４―テトラメチル・吉草
酸ビニル、２―イソプロピル―２，３―ジメチル
酪酸ビニル、マレイン酸ジメチル、マレイン酸ジ
エチル、イタコン酸ジメチル、イタコン酸ジエチ
ル、メチル―ビニル・エーテル、エチルビニルエ
ーテル、ブチルビニルエーテル、イソプロピルビ
ニルエーテル、オクチルビニルエーテル、ドデシ
ルビニルエーテル、オクタデシルビニルエーテ
ル、Ｎ―ヒドロキシメチルアクリルアミド、Ｎ―
ヒドロキシメチル・メタクリルアミド、Ｎ―
〔（２―ヒドロキシ）―エチル〕アクリルアミド、
Ｎ―〔（２―ヒドロキシ）エチル〕メタクリルア
ミド、Ｎ―ヒドロキシメチル・マレアミド酸、Ｎ
―ヒドロキシメチル・マレアミド、Ｎ，Ｎ―ジヒ
ドロキシメチル・マレアミド、Ｎ―ヒドロキシメ
チル・イタコンアミド酸、Ｎ―〔（１―ヒドロキ
シメチル）―プロピル〕―アクリルアミド、Ｎ―
〔（１―ヒドロキシメチル）プロピル〕―メタクリ
ルアミド、Ｎ―〔（１―メチル―１―ヒドロキシ
メチル）―１―エチル〕アクリルアミド、Ｎ―
〔（１―メチル―１―ヒドロキシメチル）―１―エ
チル〕メタクリルアミド、Ｎ―〔１，１，１―ト
リス（ヒドロキシメチル）―メチル〕アクリルア
ミド、Ｎ―〔１，１，１―トリス（ヒドロキシメ
チル）―メチル〕メタクリルアミド、Ｎ―〔（３
―ヒドロキシ―１，１―ジメチル）ブチル〕アク
リルアミド、Ｎ―〔（３―ヒドロキシ―１，１―
ジメチル）ブチル〕メタクリルアミド、Ｎ―
〔（２―ヒドロキシ）―エチル〕―Ｎ―メチルアク
リルアミド、Ｎ―〔（２―ヒドロキシ）エチル〕
―Ｎ―メチルメタクリルアミド、Ｎ―〔１，１―
ビス（ヒドロキシメチル）エチル〕―アクリルア
ミド及びＮ―〔１，１ビス（ヒドロキシメチル）
エチル〕メタクリルアミドからなる群から選ばれ
る特許請求の範囲第３項又は第４項記載の方法。 ８ 触媒の濃度は、反応させるモノマに対して
0.2ないし10重量％である特許請求の範囲第３項
〜第７項のいずれかに記載の方法。 ９ 適当な化粧料担体中に、一般式： 〔式中、Ｒは炭素数１ないし10個の直鎖又は分
岐鎖アルキル基を表わし、R1，R2及びR3は水素
原子又はメチル基を表わしｎは０又は１でありｎ
が１のときＸは酸素原子を表わす；ｍは０又は１
でありｍが０ならばR4は水素原子又は―COOH
基、R5は水素原子又は―CH3基であり、ｍが１な
らばR4は水素原子、R5は―COOH基である；Ｍ
は下記(i)〜(viii)に示される反復単位の少なくとも１
つを表わす： （ただしR6は水素原子又はメチル基を表わ
す） （ただしR7は水素原子又はメチル基を表わ
し、R8は炭素数１ないし18個の直鎖又は分岐鎖
アルキル基、第４級化されているか又は第４級化
されていない―（CH2）2―Ｎ（CH3）2基、―CH2
―CH2―OH基、【式】基及び ―（CH2―CH2―Ｏ）l―R′基でかつR′がメチル基
又はエチル基を表わしｌが３又は４であるものを
表わす） （ただしR9は炭素数１ないし16個の直鎖又は
分岐鎖アルキル基を表わす）、 （ただしR″は炭素数１ないし３個のアルキル
基を表わす）、 （ただしR10は炭素数１ないし17個の直鎖又は
分岐鎖飽和アルキル基を表わす）、 （ただしR11は水素原子又はメチル基を表わ
し、Ｚは炭素数１ないし６個の直鎖又は分岐鎖ア
ルキレン基であつてかつ場合により１個又は２個
のヒドロキシメチル官能基により置換されている
ものを表わし、ｐは０又は１であり、ｐが０なら
ばR13は水素原子又は―COR14基でありR14は―
OH又は―NH―R15基であり、R15は水素原子又は
Ｚ―OH基でありR12は水素原子又は―CH3基であ
り、ｐが１ならばR13は水素原子、R12は―COR14
基であり、R14は上記のものと同じ意味を表わ
す）； ｗは５〜90重量％であり、ｘは５〜90重量％で
あり、ｙは５〜60重量％である〕で表わされる反
復単位からなり、かつ1000〜500000の分子量を有
する新規コポリマーの少なくとも１種を含有する
ことを特徴とする、化粧料組成物。 １０ コポリマー0.2ないし８重量％、アルコー
ル６ないし30重量％好ましくは８ないし25重量％
を含み、残部はほぼ加圧液化した噴射用ガスから
なり、エアロゾル噴射容器に収容してある特許請
求の範囲第９項記載の組成物。 １１ コポリマー0.3ないし６重量％を含む水性
アルコール溶液であつて頭髪セツテイング用ロー
シヨンとして使用する特許請求の範囲第９項記載
の組成物。 １２ そのほかに香料、着色料、防腐剤、可塑
剤、カチオン界面活性剤、非イオン界面活性剤、
シリコーンその他の化粧料用樹脂などの化粧料補
助剤を含む特許請求の範囲第９項ないし第１１項
のいずれかに記載の組成物。[Claims] 1. General formula: [In the formula, R represents a straight chain or branched alkyl group having 1 to 10 carbon atoms, R 1 , R 2 and R 3 represent a hydrogen atom or a methyl group, n is 0 or 1, and n
When is 1, X represents an oxygen atom; m is 0 or 1
and if m is 0, R 4 is a hydrogen atom or -COOH
group, R 5 is a hydrogen atom or a -CH 3 group, and if m is 1, R 4 is a hydrogen atom and R 5 is a -COOH group; M
is at least one of the repeating units shown in (i) to (viii) below.
Represents one: (However, R 6 represents a hydrogen atom or a methyl group) (However, R 7 represents a hydrogen atom or a methyl group, and R 8 represents a straight or branched alkyl group having 1 to 18 carbon atoms, quaternized or non-quaternized -(CH 2 ) 2 -N(CH 3 ) 2 groups, -CH 2 -
CH 2 --OH group, [Formula] group, and - (CH 2 --CH 2 --O) l --R' group, where R' is a methyl group or an ethyl group and l is 3 or 4) (However, R 9 represents a straight chain or branched alkyl group having 1 to 16 carbon atoms), (However, R″ represents an alkyl group having 1 to 3 carbon atoms) (However, R10 represents a straight chain or branched chain saturated alkyl group having 1 to 17 carbon atoms), (However, R 11 represents a hydrogen atom or a methyl group, and Z is a straight or branched alkylene group having 1 to 6 carbon atoms, optionally substituted with 1 or 2 hydroxymethyl functional groups. p is 0 or 1, and if p is 0, R 13 is a hydrogen atom or -COR 14 group, and R 14 is -
OH or -NH-R 15 group, R 15 is a hydrogen atom or Z-OH group, R 12 is a hydrogen atom or -CH 3 group, and if p is 1, R 13 is a hydrogen atom, R 12 is -COR 14
R14 represents the same meaning as above); w is 5 to 90% by weight, x is 5 to 90% by weight, y is 5 to 60% by weight] A novel copolymer consisting of repeating units and having a molecular weight of 1,000 to 500,000. 2. The copolymer according to claim 1, having a molecular weight of 2,000 to 200,000. 3 a Formula (): (In the formula, R represents a straight or branched alkyl group having 1 to 10 carbon atoms, R 1 , R 2 and R 3 represent a hydrogen atom or a methyl group, n is 0 or 1, and n is 1. at least one monomer of the formula (where X represents an oxygen atom); b formula (): (In the formula, m is 0 or 1, and if m is 0,
R 4 is a hydrogen atom or a -COOH group, R 5 is a hydrogen atom or a -CH 3 group, and if m is 1, R 4 is a hydrogen atom and R 5 is a -COOH group); and c styrene, N-vinylpyrrolidone and the following (i)
At least one monomer selected from the group consisting of monomers of formulas (vi) to (However, R 6 represents a hydrogen atom or a methyl group) (However, R 7 represents a hydrogen atom or a methyl group, and R 8 represents a straight or branched alkyl group having 1 to 18 carbon atoms, a quaternized or
unclassified -(CH 2 ) 2 -N(CH 3 ) 2 groups,
-CH 2 -CH 2 -OH group,
[Formula] represents a group and -(CH 2 -CH 2 -O) l -R' group, where R' represents a methyl group or an ethyl group and l represents 3 or 4) (However, R 9 represents a straight chain or branched alkyl group having 1 to 16 carbon atoms), (However, R'' represents an alkyl group having 1 to 3 carbon atoms), () CH 2 = CH-O-R 10 ... () (However, R 10 is a straight or branched chain having 1 to 17 carbon atoms. (represents a saturated alkyl group), (However, R 11 represents a hydrogen atom or a methyl group, and Z is a linear or branched alkylene group having 1 to 6 carbon atoms, optionally substituted with 1 or 2 hydroxymethyl functional groups. represents something, p is 0 or 1, and p
If is 0, R 13 is a hydrogen atom or -COR 14 group, R 14 is -OH or -NH-R 15 group, R 15 is a hydrogen atom or Z-OH group, and R 12 is a hydrogen atom or -CH 3 groups, and if p is 1, R 13 is a hydrogen atom, R 12 is a -COR 14 group, and R 14 represents the same meaning as above); in the presence of a polymerization catalyst that generates free radicals. A general formula characterized by polymerization or solution polymerization in a suitable solvent: (However, in the formula, R 1 , R 2 , R 3 , R 4 and R 5 groups, n, m and X have the same meanings as above, and M is defined in (i) to (viii) below. represents at least one of the indicated repeating units; (In the above formula, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 ,
R 12 , R 13 , R″, p and Z have the above meanings); w is 5 to 90% by weight; x is 5% by weight;
5 to 90% by weight, and y is 5 to 60% by weight
), and
Process for producing new copolymers with molecular weights between 1000 and 500000. 4 5 to 90% by weight of at least one monomer of formula (), at least one monomer of formula ()
4. A process according to claim 3, wherein 5 to 90% by weight of a species and 5 to 60% by weight of at least one of styrene, N-vinylpyrrolidone or a monomer of formulas () to () are copolymerized. 5 Monomers of formula () are N-tert-butyl, acrylamide, N-octyl acrylamide, N-
Decyl-acrylamide, N-dodecyl acrylamide, N-[1,1 dimethyl-1-propyl]
Acrylamide, N-[(1,1 dimethyl)-1
-butyl]acrylamide, N-[(1,1-dimethyl)-1-pentyl]acrylamide, N-
5. A method according to claim 3 or claim 4, wherein the compound is selected from the group consisting of isobutoxymethylacrylamide and the corresponding methacrylamide. 6. The method according to claim 3 or 4, wherein the monomer of formula () is selected from the group consisting of acrylamide, methacrylamide, maleamic acid and itaconamic acid. 7 Monomers of formulas () to () are acrylonitrile, methacrylonitrile, methyl, ethylpropyl, isopropyl, butyl, tert-butyl, hexyl, decyl, dodecyl,
Octadecyl-, 2-hydroxy-ethyl-, 2-N,N with or without quaternization
Acrylates and methacrylates of dimethylamino-ethyl and ω-methyl or ethyl polyethylene glycol, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl laurate, vinyl stearate, vinyl pivalate, vinyl neoheptanoate, vinyl neoctanoate, Vinyl neodecanonate, vinyl 2,2,4,4-tetramethyl-valerate, vinyl 2-isopropyl-2,3-dimethylbutyrate, dimethyl maleate, diethyl maleate, dimethyl itaconate, diethyl itaconate, methyl-vinyl・Ether, ethyl vinyl ether, butyl vinyl ether, isopropyl vinyl ether, octyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, N-hydroxymethyl acrylamide, N-
Hydroxymethyl methacrylamide, N-
[(2-hydroxy)-ethyl]acrylamide,
N-[(2-hydroxy)ethyl]methacrylamide, N-hydroxymethyl maleamic acid, N
-Hydroxymethyl maleamide, N,N-dihydroxymethyl maleamide, N-hydroxymethyl itaconamidic acid, N-[(1-hydroxymethyl)-propyl]-acrylamide, N-
[(1-hydroxymethyl)propyl]-methacrylamide, N-[(1-methyl-1-hydroxymethyl)-1-ethyl]acrylamide, N-
[(1-methyl-1-hydroxymethyl)-1-ethyl]methacrylamide, N-[1,1,1-tris(hydroxymethyl)-methyl]acrylamide, N-[1,1,1-tris(hydroxy methyl)-methyl]methacrylamide, N-[(3
-Hydroxy-1,1-dimethyl)butyl]acrylamide, N-[(3-hydroxy-1,1-
dimethyl)butyl]methacrylamide, N-
[(2-hydroxy)-ethyl]-N-methylacrylamide, N-[(2-hydroxy)ethyl]
-N-methylmethacrylamide, N-[1,1-
Bis(hydroxymethyl)ethyl]-acrylamide and N-[1,1bis(hydroxymethyl)
ethyl]methacrylamide. 8 The concentration of catalyst is relative to the monomers to be reacted.
8. A method according to any of claims 3 to 7, wherein the amount is from 0.2 to 10% by weight. 9 In a suitable cosmetic carrier, the general formula: [In the formula, R represents a straight chain or branched alkyl group having 1 to 10 carbon atoms, R 1 , R 2 and R 3 represent a hydrogen atom or a methyl group, n is 0 or 1, and n
When is 1, X represents an oxygen atom; m is 0 or 1
and if m is 0, R 4 is a hydrogen atom or -COOH
group, R 5 is a hydrogen atom or -CH 3 group, if m is 1, R 4 is a hydrogen atom, R 5 is -COOH group; M
is at least one of the repeating units shown in (i) to (viii) below.
Represents one: (However, R 6 represents a hydrogen atom or a methyl group) (However, R 7 represents a hydrogen atom or a methyl group, and R 8 represents a straight or branched alkyl group having 1 to 18 carbon atoms, quaternized or non-quaternized—(CH 2 ) 2 -N(CH 3 ) 2 groups, -CH 2
-CH 2 -OH group, [Formula] group and -(CH 2 -CH 2 -O) l -R' group, where R' is a methyl group or an ethyl group and l is 3 or 4) (However, R 9 represents a straight chain or branched alkyl group having 1 to 16 carbon atoms), (However, R'' represents an alkyl group having 1 to 3 carbon atoms) (However, R10 represents a straight chain or branched chain saturated alkyl group having 1 to 17 carbon atoms), (However, R 11 represents a hydrogen atom or a methyl group, and Z is a linear or branched alkylene group having 1 to 6 carbon atoms, optionally substituted with 1 or 2 hydroxymethyl functional groups. p is 0 or 1, and if p is 0, R 13 is a hydrogen atom or -COR 14 group, and R 14 is -
OH or -NH-R 15 group, R 15 is a hydrogen atom or Z-OH group, R 12 is a hydrogen atom or -CH 3 group, and if p is 1, R 13 is a hydrogen atom, R 12 is -COR 14
R14 represents the same meaning as above); w is 5 to 90% by weight, x is 5 to 90% by weight, y is 5 to 60% by weight] A cosmetic composition characterized in that it contains at least one novel copolymer consisting of repeating units and having a molecular weight of 1,000 to 500,000. 10 0.2 to 8% by weight of copolymer, 6 to 30% by weight of alcohol, preferably 8 to 25% by weight
10. The composition according to claim 9, wherein the composition comprises a pressurized liquefied propellant gas, and the remainder is contained in an aerosol spray container. 11. A composition according to claim 9, which is a hydroalcoholic solution containing 0.3 to 6% by weight of the copolymer and is used as a hair setting lotion. 12 In addition, fragrances, colorants, preservatives, plasticizers, cationic surfactants, nonionic surfactants,
The composition according to any one of claims 9 to 11, which contains a cosmetic adjuvant such as silicone or other cosmetic resin.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU74708A LU74708A1 (en) | 1976-04-06 | 1976-04-06 | |
| LU75370A LU75370A1 (en) | 1976-07-12 | 1976-07-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52123482A JPS52123482A (en) | 1977-10-17 |
| JPS6213365B2 true JPS6213365B2 (en) | 1987-03-26 |
Family
ID=26640197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3820077A Granted JPS52123482A (en) | 1976-04-06 | 1977-04-05 | Novel copolymers and process for producing same and cosmetic composition containing thereof |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS52123482A (en) |
| AT (1) | AT364706B (en) |
| BR (1) | BR7702205A (en) |
| CA (1) | CA1111193A (en) |
| CH (1) | CH622024A5 (en) |
| DE (1) | DE2715296A1 (en) |
| FR (1) | FR2360615A1 (en) |
| GB (1) | GB1572626A (en) |
| IT (1) | IT1082486B (en) |
| NL (1) | NL7703735A (en) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2499851A1 (en) * | 1981-02-18 | 1982-08-20 | Oreal | Anhydrous nail varnish comprising (meth)acrylate ester copolymer - with e.g. sulphonamide or (meth)acrylamide deriv., in organic solvent |
| FR2530141A1 (en) * | 1982-07-13 | 1984-01-20 | Oreal | METHOD FOR PUSHING HAIR AND COSMETIC COMPOSITION FOR ITS IMPLEMENTATION |
| US4423199A (en) * | 1982-09-30 | 1983-12-27 | Rohm And Haas Company | Acrylamide containing emulsion copolymers for thickening purposes |
| GB8324858D0 (en) * | 1983-09-16 | 1983-10-19 | Unilever Plc | Hair conditioning preparation |
| DE3627969A1 (en) * | 1986-08-18 | 1988-02-25 | Basf Ag | COPOLYMERISATE, THEIR USE AS A HAIR FIXING AGENT AND THE HAIR FIXING AGENT CONTAINING THEM |
| MXPA03008714A (en) | 2002-09-26 | 2004-09-10 | Oreal | Sequenced polymers and cosmetic compositions comprising the same. |
| AU2003299070A1 (en) | 2002-09-26 | 2004-04-19 | L'oreal | Lipstick comprising a sequenced polymer |
| FR2860143B1 (en) | 2003-09-26 | 2008-06-27 | Oreal | COSMETIC COMPOSITION COMPRISING A SEQUENCE POLYMER AND A NON-VOLATILE SILICONE OIL |
| US8399001B2 (en) | 2003-11-18 | 2013-03-19 | L'oreal | Cosmetic composition comprising at least one gellan gum or derivative thereof, at least one monovalent salt, and at least one suspension compound, processes using this composition, and uses thereof |
| US8246940B2 (en) | 2003-11-18 | 2012-08-21 | L'oreal S.A. | Cosmetic composition comprising gellan gum or a derivative thereof, a fixing polymer, a monovalent salt and an alcohol, process of using the same |
| US8728451B2 (en) | 2004-03-25 | 2014-05-20 | L'oreal | Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof |
| US7976831B2 (en) | 2004-04-02 | 2011-07-12 | L'oreal S.A. | Method for treating hair fibers |
| FR2868305B1 (en) | 2004-04-02 | 2006-06-30 | Oreal | CAPILLARY TREATMENT PROCESS AND USE THEREOF |
| US8968707B2 (en) | 2004-05-07 | 2015-03-03 | L'oreal | Composition packaged in an aerosol device, comprising at least one anionic fixing polymer, at least one silicone oxyalkylenated in the alpha and omega positions of the silicone chain, and at least one propellant |
| JP2006199664A (en) * | 2005-01-24 | 2006-08-03 | Goo Chemical Co Ltd | Base agent for hair cosmetic and hair cosmetic |
| FR2882518B1 (en) | 2005-02-28 | 2012-10-19 | Oreal | COLORING OF PARTICULAR HUMAN KERATINIC MATERIALS BY DRY THERMAL TRANSFER OF DIRECT ANTHRAQUINONIC COLOR, COMPOSITION COMPRISING THE SAME, AND PROCESS FOR PREPARING THE SAME |
| FR2882519B1 (en) | 2005-02-28 | 2008-12-26 | Oreal | COLORING OF PARTICULAR HUMAN KERATINIC MATERIALS BY DRY THERMAL TRANSFER OF AZOMETHINIC DIRECT COLORANT COMPOSITION COMPRISING SAID COLORING DYE AND PROCESS FOR PREPARING THE SAME |
| FR2882521B1 (en) | 2005-02-28 | 2008-05-09 | Oreal | COLORING OF KERATINIC SUBSTANCES, PARTICULARLY HUMAN BY DRY THERMAL TRANSFER OF A DIRECT COLOR, COMPOSITION COMPRISING SAID COLOR, AND PROCESS FOR PREPARING THE SAME |
| US7744859B2 (en) | 2005-04-29 | 2010-06-29 | L'oreal S.A. | Semipermanent hair shaping method |
| US7824664B2 (en) | 2005-04-29 | 2010-11-02 | L'oreal S.A. | Semipermanent hair shaping method |
| FR2904320B1 (en) | 2006-07-27 | 2008-09-05 | Oreal | POLYMER SEQUENCES, AND PROCESS FOR THEIR PREPARATION |
| FR2904536B1 (en) | 2006-08-04 | 2008-11-07 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE CARRAGENAN LAMBDA-TYPE POLYSACCHARIDE AS AEROSOL, PROCESS FOR COSMETIC TREATMENT OF KERATIN FIBERS AND USE OF THE COMPOSITION |
| FR2964317B1 (en) | 2010-09-06 | 2013-04-12 | Oreal | COSMETIC COMPOSITION COMPRISING A FIXING POLYMER AND A PARTICULAR THICKENER AND STAPLING USES |
| EP2651372B2 (en) | 2010-12-14 | 2023-10-25 | L'oreal | Aerosol device having two compartments including an alcoholic or hydroalcoholic hairstyling composition, and hairstyling method |
| WO2012164065A2 (en) | 2011-06-01 | 2012-12-06 | L'oreal | Process for treating straightened keratin fibres |
| FR2992199B1 (en) | 2012-06-21 | 2015-07-17 | Oreal | COSMETIC COMPOSITION COMPRISING AQUEOUS DISPERSION OF HYDROPHOBIC SILICA AEROGEL PARTICLES AND A PARTICULAR ALCOHOL |
| WO2013190080A2 (en) | 2012-06-21 | 2013-12-27 | L'oreal | Cosmetic composition comprising hydrophobic silica aerogel particles, a wax, a hydrocarbon oil and a fatty alcohol and/or a fatty acid |
| FR3002143B1 (en) | 2013-02-15 | 2015-02-20 | Oreal | COSMETIC COMPOSITION COMPRISING A VINYLFORMAMIDE / VINYLFORMAMINE COPOLYMER, A CELLULOSIC THICKENING POLYMER AND AN AMPHOTERE OR ZWITTERIONIC SURFACTANT |
| FR3004901B1 (en) | 2013-04-30 | 2016-02-12 | Oreal | MULTI-ORIFICE DIFFUSION AEROSOL DEVICE FOR DRY WASHING HAIR |
| FR3004902A1 (en) | 2013-04-30 | 2014-10-31 | Oreal | MULTI-ORIFICE DIFFUSION AEROSOL DEVICE FOR SHAPING HAIR AND / OR MAINTAINING HAIR |
| FR3004929B1 (en) | 2013-04-30 | 2015-04-10 | Oreal | AEROSOL DEVICE BASED ON SEBUM ABSORBENT POWDER AND CALCIUM CARBONATE |
| CN105283223B (en) | 2013-06-17 | 2021-10-15 | 莱雅公司 | Cosmetic composition comprising mineral wax, fatty acid, mineral oil, surfactant, ester of fatty acid and/or fatty alcohol and fixing polymer |
| FR3022770B1 (en) | 2014-06-30 | 2016-07-29 | Oreal | AEROSOL DEVICE BASED ON CALCIUM SALT, FIXING POLYMER, SURFACTANT AND WATER |
| FR3027800B1 (en) | 2014-10-29 | 2018-01-26 | L'oreal | COMPOSITION BASED ON SEBUM-COATING AND / OR ABSORBENT POWDER AND ALUMINUM SALT |
| FR3027798B1 (en) | 2014-10-29 | 2017-12-22 | Oreal | COMPOSITION BASED ON SEBUM-COATING AND / OR ABSORBENT POWDER AND ZINC SALT |
| FR3031437B1 (en) | 2015-01-08 | 2017-01-13 | Oreal | AEROSOL DEVICE FOR SHAPING HAIR AND / OR MAINTAINING HAIR |
| FR3031453B1 (en) | 2015-01-08 | 2017-01-13 | Oreal | CAPILLARY TREATMENT METHOD PROVIDING BRILLIANCE USING AEROSOL DEVICE |
| FR3032119B1 (en) | 2015-01-29 | 2017-01-20 | Oreal | METHOD FOR TREATING HAIR WITH AT LEAST ONE SILICONE FUNCTIONALIZED BY AT LEAST ONE ALCOXYSILANE MOTIF, AND STEAM |
| FR3032117B1 (en) | 2015-01-29 | 2018-03-16 | L'oreal | COMPOSITION COMPRISING A SILICONE FUNCTIONALIZED BY AT LEAST ONE ALCOXYSILANE MOTIF AND A NONIONIC OR ANIONIC FIXING POLYMER |
| FR3032118B1 (en) | 2015-01-29 | 2018-03-16 | L'oreal | AEROSOL COMPOSITION COMPRISING A SILICONE FUNCTIONALIZED BY AT LEAST ONE ALCOXYSILANE MOTIF AND AN AMPHOTERE AND / OR CATIONIC FIXING POLYMER |
| US11395794B2 (en) | 2015-12-14 | 2022-07-26 | L'oreal | Process for treating keratin fibres using an aqueous composition comprising a combination of particular alkoxysilanes |
| US10524999B2 (en) | 2015-12-14 | 2020-01-07 | L'oreal | Composition comprising a combination of particular alkoxysilanes and a fatty substance |
| FR3063607B1 (en) | 2017-03-09 | 2021-07-23 | Oreal | AEROSOL DEVICE FOR DRY WASHING AND HAIR TREATMENT |
| FR3063605B1 (en) | 2017-03-09 | 2021-07-23 | Oreal | AEROSOL DEVICE FOR HAIR SHAPING AND / OR HAIR MAINTENANCE |
| FR3063606B1 (en) | 2017-03-09 | 2021-07-23 | Oreal | AEROSOL DEVICE FOR HAIR SHAPING AND / OR HAIR MAINTENANCE |
-
1977
- 1977-04-05 JP JP3820077A patent/JPS52123482A/en active Granted
- 1977-04-05 NL NL7703735A patent/NL7703735A/en not_active Application Discontinuation
- 1977-04-05 AT AT235877A patent/AT364706B/en not_active IP Right Cessation
- 1977-04-05 IT IT6775077A patent/IT1082486B/en active
- 1977-04-05 DE DE19772715296 patent/DE2715296A1/en not_active Withdrawn
- 1977-04-05 CH CH429677A patent/CH622024A5/en not_active IP Right Cessation
- 1977-04-05 FR FR7710220A patent/FR2360615A1/en active Granted
- 1977-04-05 GB GB1445177A patent/GB1572626A/en not_active Expired
- 1977-04-06 CA CA275,689A patent/CA1111193A/en not_active Expired
- 1977-04-06 BR BR7702205A patent/BR7702205A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT364706B (en) | 1981-11-10 |
| BR7702205A (en) | 1978-07-25 |
| FR2360615A1 (en) | 1978-03-03 |
| DE2715296A1 (en) | 1977-10-27 |
| IT1082486B (en) | 1985-05-21 |
| ATA235877A (en) | 1981-04-15 |
| NL7703735A (en) | 1977-10-10 |
| GB1572626A (en) | 1980-07-30 |
| JPS52123482A (en) | 1977-10-17 |
| CA1111193A (en) | 1981-10-20 |
| FR2360615B1 (en) | 1981-02-13 |
| CH622024A5 (en) | 1981-03-13 |
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