AU5648400A - Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one photoprotective agent - Google Patents
Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one photoprotective agent Download PDFInfo
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- AU5648400A AU5648400A AU56484/00A AU5648400A AU5648400A AU 5648400 A AU5648400 A AU 5648400A AU 56484/00 A AU56484/00 A AU 56484/00A AU 5648400 A AU5648400 A AU 5648400A AU 5648400 A AU5648400 A AU 5648400A
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- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 32
- 230000003711 photoprotective effect Effects 0.000 title claims abstract description 22
- 239000002537 cosmetic Substances 0.000 title claims abstract description 21
- 229920001577 copolymer Polymers 0.000 title claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 title claims description 34
- -1 amino benzoates Chemical class 0.000 claims abstract description 75
- 210000004209 hair Anatomy 0.000 claims abstract description 30
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 8
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical class CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 claims abstract description 6
- 150000001565 benzotriazoles Chemical class 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 5
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 4
- 150000003918 triazines Chemical class 0.000 claims abstract description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012964 benzotriazole Substances 0.000 claims abstract description 3
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical class CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000004756 silanes Chemical class 0.000 claims abstract description 3
- KKJKXQYVUVWWJP-UHFFFAOYSA-N 4-[(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound CC1(C)C2CCC1(C)C(=O)C2=CC1=CC=C(S(O)(=O)=O)C=C1 KKJKXQYVUVWWJP-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000012216 screening Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical class C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 238000007493 shaping process Methods 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 claims description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 3
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical compound C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 claims description 2
- QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical compound C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 2
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical group C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical class NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 claims description 2
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 239000002280 amphoteric surfactant Substances 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005131 dialkylammonium group Chemical group 0.000 claims description 2
- 229940008099 dimethicone Drugs 0.000 claims description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 210000004709 eyebrow Anatomy 0.000 claims description 2
- 210000000720 eyelash Anatomy 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 2
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 claims 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 abstract description 2
- ZRHAGDPKFFHVEY-UHFFFAOYSA-N n-phenyl-1,3,5-triazin-2-amine Chemical compound N=1C=NC=NC=1NC1=CC=CC=C1 ZRHAGDPKFFHVEY-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003902 salicylic acid esters Chemical class 0.000 abstract description 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 6
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 239000003223 protective agent Substances 0.000 abstract 2
- 238000010526 radical polymerization reaction Methods 0.000 abstract 2
- 125000000355 1,3-benzoxazolyl group Chemical class O1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000005855 radiation Effects 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000195940 Bryophyta Species 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000011929 mousse Nutrition 0.000 description 5
- 239000003380 propellant Substances 0.000 description 5
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 4
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 4
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 4
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000004224 protection Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 2
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 description 2
- 238000000861 blow drying Methods 0.000 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 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 229960001173 oxybenzone Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229960000368 sulisobenzone Drugs 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- OMWSZDODENFLSV-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OMWSZDODENFLSV-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- KAIHOCOWYAMXQY-OWOJBTEDSA-N (e)-3-cyanoprop-2-enoic acid Chemical compound OC(=O)\C=C\C#N KAIHOCOWYAMXQY-OWOJBTEDSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- UYZZHENGTKPYMN-UHFFFAOYSA-N 4-hydroxy-5-(2-hydroxy-4-methoxy-5-sulfobenzoyl)-2-methoxybenzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC(S(O)(=O)=O)=C(OC)C=C1O UYZZHENGTKPYMN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 241001484259 Lacuna Species 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- HEAHZSUCFKFERC-LRVMPXQBSA-N [(2e)-2-[[4-[(z)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)\C2=C/C(C=C1)=CC=C1\C=C/1C(=O)C2(CS(O)(=O)=O)CCC\1C2(C)C HEAHZSUCFKFERC-LRVMPXQBSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940111759 benzophenone-2 Drugs 0.000 description 1
- 229940079894 benzophenone-9 Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- HHBIQTAAJCSNCD-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone;bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O.OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O HHBIQTAAJCSNCD-UHFFFAOYSA-N 0.000 description 1
- YEAYGXLRPMKZBP-KQGICBIGSA-N bis(2-hydroxyethyl)azanium;(e)-3-(4-methoxyphenyl)prop-2-enoate Chemical compound OCCNCCO.COC1=CC=C(\C=C\C(O)=O)C=C1 YEAYGXLRPMKZBP-KQGICBIGSA-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
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KAOPHVRFVWFGRN-UHFFFAOYSA-M decyl(trimethyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCC[N+](C)(C)C KAOPHVRFVWFGRN-UHFFFAOYSA-M 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229960004960 dioxybenzone Drugs 0.000 description 1
- QDCHWIWENYCPIL-UHFFFAOYSA-L disodium;4-hydroxy-5-(2-hydroxy-4-methoxy-5-sulfonatobenzoyl)-2-methoxybenzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC(S([O-])(=O)=O)=C(OC)C=C1O QDCHWIWENYCPIL-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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 description 1
- 229960003747 ecamsule Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 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 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 1
- SOXAGEOHPCXXIO-UHFFFAOYSA-N meradimate Chemical compound CC(C)C1CCC(C)CC1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-UHFFFAOYSA-N 0.000 description 1
- 229960002248 meradimate Drugs 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- PVWXTVUZGJXFJQ-UHFFFAOYSA-N methyl 4-methyl-3-phenyl-2-propan-2-ylpent-2-enoate Chemical compound COC(=O)C(C(C)C)=C(C(C)C)C1=CC=CC=C1 PVWXTVUZGJXFJQ-UHFFFAOYSA-N 0.000 description 1
- MJVGBKJNTFCUJM-UHFFFAOYSA-N mexenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C=C1 MJVGBKJNTFCUJM-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 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
-
- 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
-
- 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Toxicology (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Cosmetic composition comprises a silicone-acrylate copolymer produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a silicone having oxyalkylene groups and a photo protective agent selected from a list of substances. Cosmetic composition comprises a silicone-acrylate copolymer produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a silicone having oxyalkylene groups and a photo protective agent selected from: (1) dibenzoylmethanes; (2) benzylidene camphor derivatives of formula (I); (3) benzimidazoles and benzoxazoles of formula (II); (4) benzophenone-functional silanes or polyorganosiloxanes; (5) anthranilates; (6) benzotriazoles, benzotriazole silicones; and (7) triazines particularly 2,4,6-tris-p-(2'-ethylhexyl-1'-acyl carbonyl)anilino-1,3,5-triazine, salicylates particularly methyl or octyl salicylates, p-(dimethyl)amino benzoates, alkyl 2-cyano-3,3-diphenylacrylates, metal oxide nanopigments; (8) 3,4'-methyl benzylidene camphor, 3-benzylidene camphor, the methyl sulfate of (3,4'-trimethylammonium)-benzylidene camphor and the acid of 3-(4'-sulfobenzylidene) camphor. R7, R9 = H, halo, OH, (un)saturated 1-10C alkyl, (un)saturated 1-10C alkoxy or SO3H; R10 = H or SO3H; R8 = OH or OR11; R11 = (un)saturated 1-10C alkyl or a group of formula (i)-(iii); W = O or NH; R17 = H or SO3H; R18 = (un)saturated 1-10C alkoxy, 5-R19-2-benzoxazolyl or 5-R19-1H-imidazol-2-yl; R19 = H or SO3H. R12 = H or SO3H; Z = O or NH; R13-R16 = H, halo, OH, (un)saturated 1-10C alkyl, (un)saturated 1-10C alkoxy or SO3H. An Independent claim is also included for a hair styling method using the above composition.
Description
AUSTRALIA
Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT
L'OREAL
Title: COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE/ACRYLATE COPOLYMER AND AT LEAST ONE PHOTOPROTECTIVE AGENT Applicant Invention The following statement is a full description of this invention, including the best method of performing it known to me/us: 1Al COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE/ACRYLATE COPOLYMER AND AT LEAST ONE PHOTOPROTECTIVE AGENT The invention relates to a cosmetic composition comprising at least one specific silicone/acrylate copolymer and at least one photoprotective agent. The invention also relates to a cosmetic process, in particular a process for fixing 10 and/or holding the hairstyle by using the said composition, as well as to the use of this composition for the manufacture of a cosmetic formulation intended in particular for holding and/or shaping the hairstyle.
According to the invention, the term "photoprotective agent" is generally intended to denote any compound or combination of compounds which is(are) known per se and which, by mechanisms, which are also known per se, of absorption and/or reflection and/or scattering of UV-A and/or UV-B radiation, makes it possible to prevent, or at least limit, the contact of the said radiation with the surface of the hair onto which this or these compounds have been applied. In other words, these compounds can be UV-absorbing photoprotective organic screening agents or UV-scattering and/or UV-reflecting mineral (nano)pigments, as well as mixtures thereof.
Among hair products, in particular those intended for shaping and/or holding the hairstyle which are most widely available on the cosmetics market, there may be distinguished spray compositions essentially consisting of a solution, usually an alcoholic or aqueous solution, and one or more materials.
When the compositions are intended for fixing and/or holding the hairstyle, these materials are generally polymeric resins, whose function is to form welds between the hairs, and these are also known as S 10 fixing materials, mixed with various cosmetic o oo adjuvants. These compositions are generally packaged •go• either in a suitable aerosol container placed under pressure with the aid of a propellant, or in a pump- •.dispenser bottle.
oo 15 Hair gels and hair mousses which are generally applied to wet hair before blow-drying or setting the hair are also known. A drying or blowdrying operation is then carried out in order to shape and fix the hairstyle. These gels or mousses can also contain polymeric resins.
It is known that light radiation with wavelengths of between 280 nm and 400 nm damage the hair when a person is exposed to this radiation for too long. In particular, rays with wavelengths of between 280 nm and 320 nm, which are known as UV-B rays, embrittle the hair and degrade its various constituents, in particular keratin.
UV-A rays, with wavelengths of between 320 nm and 400 nm, are themselves capable of modifying the natural colour of the hair, in particular in the case of light-coloured hair. UV-A rays also cause a loss of elasticity of the hair, which becomes dry and brittle, especially at the tips.
Hair compositions comprising photoprotective agents capable of screening out UV-A and UV-B rays have already been proposed. However, these hair compositions 10 are not entirely satisfactory, since too small a e eo proportion of photoprotective agents become fixed to the hair. Consequently, the protection actually obtained, after applying the hair composition to the hair, is far from equal to the expected protection.
What is more, the photoprotective agents .'.which were initially fixed to the hair do not remain thereon long enough to give the person suitable and long-lasting protection. The hair is thus subjected to natural solar radiation, i.e. radiation containing harmful UV-A and UV-B rays, only a short time after applying the hair composition to the hair.
There is thus a need to find cosmetic compositions, in particular for holding and/or fixing the hairstyle, which do not have the set of drawbacks mentioned above, and which in particular fix the hairstyle well, while at the same time screening out solar radiation sufficiently and affording good cosmetic properties.
The Applicant has discovered, surprisingly and unexpectedly, that when certain silicone/acrylate copolymers are combined with photoprotective agents, it is possible to obtain cosmetic compositions which satisfy the requirements expressed above.
One subject of the invention is a cosmetic composition comprising, in a cosmetically acceptable medium, at least one silicone/acrylate copolymer and at least one photoprotective agent, the silicone/acrylate 0 10 copolymer being obtained by radical-mediated polymerization of at least one ethylenically unsaturated monomer in the presence of at least one silicone derivative comprising oxyalkylene groups.
Another subject of the invention relates to a cosmetic hair process, in particular a process for fixing and/or holding the hairstyle using the said composition.
Yet another subject of the invention relates to the use of this composition for the manufacture of a cosmetic hair formulation which is intended in particular for holding and/or shaping the hairstyle.
The silicone/acrylate copolymers particularly targeted by the present invention are those described in International patent application WO 99/04750. In particular, the copolymer sold by BASF under the name Luviflex Silk is preferred. This polymer is a grafted copolymer of tert-butyl acrylate/methacrylic acid and silicone copolyol.
Preferably, the monomer corresponds to formula (Ia)
X-C-CR
7
=CHR
6 (Ia)
O
in which: X is chosen from the group comprising OH, OM, OR 8
NH
2 NHR' and N(R 8 2 10 M is a cation chosen from Na K Mg+, NH alkylammonium, dialkylammonium, trialkylammonium o. and tetraalkylammonium; the radicals R 8 may be identical or different and are chosen from the group comprising eg 15 hydrogen, linear or branched C 1 to C 40 alkyl groups, mono- or polyhydroxylated C 1 to C 40 alkyl groups, optionally substituted with one or more alkoxy, amino or carboxyl groups, hydroxylated polyethers, and N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl, 20 2-ethoxyethyl, hydroxypropyl, methoxypropyl and ethoxypropyl groups;
R
7 and R 6 are chosen, independently of each other, from the group comprising hydrogen, linear or branched C 1 to C 8 alkyl groups, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl groups, and CN, COOH and COOM groups.
In particular, the monomers of formula (Ia) are acrylic acid and its salts, esters or amides.
The esters may be derivatives of linear Ci to C 40 alkyls, of branched C 3 to C 40 alkyls or of C 3 to C 40 carboxylic alcohols, of polyfunctional alcohols containing 2 to 8 hydroxyls, such as ethylene glycol, hexylene glycol, glycerol and 1,2,6-hexanetriol, of amino alcohols or of alcohol ethers such as methoxymethanol and ethoxyethanol, or polyalkylene glycols.
The monomers of formula (Ia) may also be 10 chosen from N,N-dialkylaminoalkyl acrylates and methacrylates and N-dialkylaminoalkyl-acrylamides and -methacrylamides, the amide group possibly being unsubstituted, N-alkyl- or N-alkylamino-monosubstituted or N,N-dialkylamino-disubstituted, the alkyl or alkylamino groups being derived from linear Ci to C 40 or branched C 3 to C 40 carboxylic units.
The monomers of formula (Ia) which can be used may also be substituted compounds derived from acrylic acid or its salts, esters or amides. Mention may be made, for example, of methacrylic acid, ethacrylic acid and 3-cyanoacrylic acid.
Other monomers which are particularly suitable are C 1 to C 40 vinyl and allyl esters, linear C 3 to C 40 carboxylic acids or C 3 to C 40 carboxycyclic acids, vinyl or allyl haldides, vinyllactams, preferably vinylpyrrolidone and vinylcaprolactam, heterocyclic compounds substituted with vinyl or allyl groups, preferably vinylpyridine, vinyloxazoline and allylpyridine, N-vinylimidazoles, diallylanines, vinylidene chloride, carbon-based unsaturated compounds, such as styrene or isoprene, and acrylic or methacrylic acid derivatives quaternized with epichlorohydrin.
Other monomers which may finally be mentioned are N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds such as styrene and isoprene, and acrylic or *6 10 methacrylic acid derivatives quaternized with epichlorohydrin.
Monomers which are most particularly preferred are acrylic, methacrylic and ethacrylic acid; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-thylhexyl and decyl acrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl 99*9 methacrylate; methyl, ethyl, propyl, n-butyl, isobutyl, **t-butyl, 2-ethylhexyl and decyl ethacrylate; ,Does,2,3-ihydroxypropyl acrylate; 2,3-dihydroxypropyl methacrylate; 2-dihydroxyethyl acrylate; hydroxypropyl acrylate; 2-hydroxyethyl methacrylate; 2-hydroxyethyl ethacrylate; 2-methoxyethyl acrylate; 2-ethoxyethyl methacrylate; 2-ethoxyethyl ethacrylate; hydroxypropyl methacrylate; glyceryl monoacrylate; glyceryl monomethacrylate; polyalkylene glycol (meth)acrylates, unsaturated sulphonic acids, acrylamide, methacrylamide, ethacrylamide, N,N-dimethylacrylamide, N-ethylacrylamide, N-ethylmethacrylanide, 1-vinyl- 8 imidazole, N,N-dimethylaminoethyl (meth)acrylate, maleic acid, fumaric acid, maleic anhydride and its monoesters, crotonic acid, itaconic acid, vinyl ethers, vinylformamide, vinylamine, vinylpyridine, vinylimidazole, vinylfuran, styrene, styryl sulphonate and allyl alcohol, and mixtures thereof.
The monomer can also contain silicon or fluorine atoms or alternatively thio groups. The monomers can be neutralized if they contain acid eq 10 groups, this being carried out before or after the polymerization, and partially or totally, so as to adjust the solubility or the degree of dispersion in water to the desired level. Agents serving for the *0*S [•neutralization which may be used are mineral bases, e such as sodium carbonate, and organic bases such as amino alcohols, for instance alkanolamines such as methanolamine, 2-amino-2-methyl-l-propanol or triethanolamine, and diamines such as lysine.
The monomers can also be quaternized when they contain a basic nitrogen atom. If they contain at least two ethylenic double bonds, the monomers can be partially crosslinked.
The silicone derivatives are in particular the compounds known under the INCI name of dimethicone copolyols or silicone surfactants. Mention may be made of those sold under the brand names Abil® by Goldschmidt, Alkasil® by Rhone-Poulenc, silicone Polyol Copolymer® by Genesee, Besil® by Wacker, Silwet® by OSI or Dow Corning 190® by Dow Corning.
Among the preferred monomers are those which have the formula I below: n- P .1 in which formula (I) 2 R is chosen from CH 3 and the group
II
R~ is chosen from CH 3 and the groupR 10 R 4 is chosen from hydrogen, CH 3 and the groups .00. ix
£M
0: 0 0 R6 is ahn r Caanic Ctthe4 group hcRcncoti R is chosen from H d group Hi c hy nronts 0 schosen from 1 dtogCn, aihtCH hdarbons, Cgr touCs oooo.' :Sr 3
R
1 i R* is a rai oC0g op wh c a ot i *ino, cab orsupoaegrusanifc0R s -cRhosn orgni C to C40 ali oupi hyrocanonsC3toin aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: [lacuna] Among the preferred silicone derivatives (b) are those which have the formula I below: i FO I R3-2 xl~l Y in which formula
R
2 is chosen from CH 3 and the group
R
3 is chosen from CH 3 and the group R 2
R
4 is chosen from hydrogen, CH 3 and the groups RF1 -h-0
RI
t$aw
R
1
GN
o
P
/o I t
C
11
R
6 is a C 1 to C 40 organic group which can contain amino, carboxyl or sulphonate groups, and if c=0, R 6 is the anion of an inorganic acid; the radicals R 1 may be identical or different and are chosen from Ci to C 20 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: 10 n is an integer between 1 and 6, x and y are integers chosen such that the molecular weight of the polysiloxane is between 300 and 30,000, a and b are integers between 0 and 50, and 15 c is 0 or 1.
R
1 is preferably chosen from methyl, ethyl, propyl, butyl, isobutyl, pentyl, isopentyl, hexyl, octyl, decyl, dodecyl and octadecyl groups, cycloaliphatic radicals, in particular cyclohexyl groups, aromatic groups, in particular phenyl or naphthyl groups, and mixtures of aromatic and aliphatic radicals, such as benzyl and phenylethyl, and also tolyl and xylyl.
The preferred radicals R 4 are those having the formula -(CO)c-R 6
R
6 being an alkyl, cycloalkyl or aryl containing 1 to 4 carbon atoms which can contain additional groups such as NH 2 COOH and/or SO 3
H.
The preferred radicals R 6 are those for which c=0, which are phosphates or sulphates.
The silicone derivatives which are particularly preferred are those having the general formula below:
CH.
I
The preferred copolymers are the watersoluble silicone/acrylate copolymers or those whose dispersibility in water is such that, in a 15 water/ethanol mixture dosed at 50/50 by volume, they are soluble in a proportion of greater than 0.1 g/ and preferably greater than 0.2 g/1.
The composition advantageously comprises, as a relative percentage by weight of the composition, from 0.1% to 20% of silicone/acrylate copolymer and preferably from 0.5% to The composition advantageously comprises, as a relative percentage by weight of the composition, a relative percentage by weight of the composition, 13 from 0.1% to 20% of photoprotective agent, and preferably from 0.2% to Among the UV-A-active organic screening agents which can be used according to the invention, mention may be made of: dibenzoylmethane derivatives; the UV-A-active screening agents of formula I below: SR R I
I
O
10 in which:
S
R
7 and R 9 which may be identical or different, denote a hydrogen, a halogen, an OH radical, a saturated or unsaturated, linear or branched Ci-Clo alkyl radical; a saturated or unsaturated, linear or 15 branched Ci-Clo alkoxy radical or an HS03 group; Rio denotes hydrogen or HSO 3
R
8 denotes hydroxyl; a group OR 11 in which
R
11 denotes a saturated or unsaturated, linear or branched Ci-Clo alkyl radical; or a group of the following structure: 12 in which R 12 denotes hydrogen or HSO 3 or alternatively a group of the following formula:
COOR
1 3 14 or alternatively a group of the following formula: .R1 16 10 in which: Z denotes an oxygen atom or an -NHradical; R13, R14, R15 and R16, which may be identical 15 radical, a saturated or unsaturated, linear or branched C1-Cjo alkyl radical; a saturated or unsaturated, linear or branched Ce-CIo alkoxy radical or an HSO3 group; the UV-A-active screening agents of the benzimidazole or benzoxazole type of formula (II) below:
R
R
18 in which: W denotes an oxygen atom or an -NHradical,
R
17 denotes hydrogen or HSO 3
R
18 denotes a linear or branched alkoxy radical containing from 1 to 10 carbon atoms approximately or a group of the following formula: IN Ri in which Y represents an oxygen atom or an -NH- radical and R 19 denotes hydrogen or HSO 3
R
19 denotes hydrogen or HSO 3 benzophenone derivatives such as those of formula (III) below: R
OH
R 2 OR 0 in which:
R
20 denotes hydrogen or a saturated or unsaturated, linear or branched Ci-Cio alkyl radical;
R
21 and R 22 which may be identical or different, denote a hydrogen, a halogen, an OH radical, a saturated or unsaturated, linear or branched C 1 -Clo alkyl radical; a saturated or unsaturated, linear or branched C 1 -Clo alkoxy radical or an HSO 3 group;
R
23 denotes hydrogen; OH; a saturated or unsaturated, linear or branched Ci-Cio alkyl radical or 10 a saturated or unsaturated, linear or branched C 1 -Cio alkoxy radical;
R
24 denotes OH, a hydrogen atom or a saturated or unsaturated, linear or branched Ci-Cio alkyl radical; silane derivatives or polyorganosiloxanes containing a benzophenone group, such as those described in documents EP-A-0 389 377, FR-A-2 657 351 and EP-A-0 655 453; anthranilates; benzotriazoles and benzotriazole silicones; mixtures thereof.
Benzotriazoles or benzotriazole derivatives which are preferably used are those of formula (I) below: 17 N OH
I
A
in which: A denotes hydrogen or a divalent radical
-L-W-
Y, which may be identical or different, are chosen from CI-Cio alkyl radicals, halogens, C 1 -Clo alkoxy radicals and sulphonic groups, it being understood that, in the latter case, two adjacent radicals Y on the same aromatic nucleus can together 10 form an alkylidenedioxy group in which the alkylidene group contains 1 or 2 carbon atoms; with the proviso "that the alkyl radicals Y are other than a sulphonic group when A is other than hydrogen; n is 1, 2 or 3; 15 L is a divalent radical of formula (II) below: (CH) p-CH-CH2
(II)
z Z in which: X represents 0 or NH, Z represents hydrogen or a Ci-C 4 alkyl radical, inclusive, 18 n is an integer between 0 and 3 m is 0 or 1, p represents an integer between1 and W is a radical of formula or 10 inclusive; below: R R ~R R B-Si Si o} Si B R -R R r s 0 0 0000 or Si-0
R
I
R
R
I
-Si -0
I
t -Si(R )3 in which: R, which may be identical or different, are chosen from CI-Co 0 alkyl, phenyl and 3,3,3-trifluoropropyl radicals, at least 80%, in numerical terms, of the radicals R being methyl, B, which may be identical or different, are chosen from the radicals R and the radical V of the following formula: 19 N OH
N
L
in which Y, n and L have the same meanings indicated above; r is an integer between 0 and 50 inclusive, 5 and s is an integer between 1 and 20 inclusive, and if s=0, at least one of the two radicals B denotes V; u is an integer between 1 and 6 inclusive, and t is an integer between 0 and 10 inclusive, it being understood that t u is greater than or equal to 3.
The benzotriazole derivatives of formula (I) are screening agents that are already known per se.
They are described and prepared according to the syntheses indicated in patents US-4 316 033 and US-4 328 346; EP-B-0 354 145 and EP-B-0 392 883 and EP-B-0 660 701 (forming an integral part of the content of the description).
Among the dibenzoylmethane derivatives which fall particularly suitably into the context of the present invention, mention may be made in particular, in a non-limiting manner, of: 2-methyldibenzoylmethane 4-methyldibenzoylmethane 4-i sopropyldibenzoylmethane 4-tert-butyldibenzoylnethane 2,4-dimethyldibenzoylinethane 4,4 '-diisopropyldibenzoylmethane 4, 4'-dimethoxydibenzoylmethane 4-tert-butyl-4' -methoxydibenzoylmethane 2-methyl-5-isopropyl-4 '-methoxydibenzoylmethane -2-methyl-5-tert-butyl-4' -methoxy- **:dibenzoylmethane 2, 4-dimethyl-4' -methoxydibenzoylmethane 2, 6-dimethyl-4-tert-butyl-4 '-methoxydibenzoylmethane Among the dibenzoylmethane derivatives mentioned above, the one most particularly preferred for use according to the present invention is 4-(tertbutyl) -4 -methoxydibenzoylmethane, in particular the product sold under the trade name "Parsol 1789" by the company Givaudan, this screening agent thus corresponding to the following structural formula: 0 0 C ZN C OCH 3 3C
CH
3 Another preferred dibenzoylmethane derivative according to the present invention is 4-isopropyldibenzoylmethane, screening agent sold under the name "Eusolex 8020" by the company Merck and corresponding to the following structural formula: 0 0 Ili II
H
3 C C H2 C MC
O
\CH
3 The compounds of structures above are described, respectively, in US patent 4 585 597 and patent applications FR 2 236 515, 2 282 426, 2 645 148, 2 430 938 and 2 592 380.
9* o One compound of formula which is 1 0 particularly preferred is benzene-1,4-bis(3methylidene-10-camphorsulphonic acid), such as the product sold under the name Mexoryl SX by the company Chimex.
Benzene-1,4-bis(3-methylidene-10- 15 camphorsulphonic acid) and its various salts (compound which are described in particular in patent applications FR-A-2 528 420 and FR-A-2 639 347, are screening agents that are already known per se (broadband screening agents) and that are in fact capable of absorbing ultraviolet rays with wavelengths of between 280 nm and 400 nm, with absorption maxima between 320 nm and 400 nm, in particular at about 345 nm. These screening agents correspond to the following general formula: in which D denotes a hydrogen atom, an alkali metal or a radical NH(R 25 3 in which the radicals R 25 which may be identical or different, denote a hydrogen atom, a CI-C 4 alkyl or hydroxyalkyl radical or a group Mn+/n, denoting a multivalent metal cation in which n is equal to 2, 3 or 4, M' preferably denoting a metal cation chosen from Ca 2 Zn2, Mg 2 Ba 2 A13l and Zr".
It is clearly understood that the compounds of formula 9 0 10 above can give rise to the "cis-trans" isomer around one or more double bond(s) and that all the *909 oe* isomers fall within the context of the present invention.
Examples of specific benzimidazole compounds corresponding to formula (II) which may be mentioned
S.
are: benzene-1,4-bis(benzimidazol-2-yl-5sulphonic acid), benzene-1,4-bis(benzoxazol-2-yl-5-sulphonic acid); as well as the partially or totally neutralized forms thereof.
Among the benzophenone derivatives of formula (III) which may be mentioned more particularly are those chosen from the group consisting of: 2, 4-dihydroxybenzophenone (benzophenone-1), such as the product sold under the name Uvinul 400 by
BASF;
2, 2' -tetrahydroxybenzophenone (benzophenone-2), such as the product sold under the name Uvinul D50 by BASF; 2-hydroxy-4-methoxybenzophenone, also known as oxybenzone (benzophenone-3), such as the product sold under the name Uvinul M40 by BASF; 2 -hydroxy-4 -methoxybenzophenone- acid, also known as sulisobenzone (benzophenone-4), such as the product sold under the name Uvinul MS40 by BASF; as well as the sodium sulphate form thereof 15 2,2' -dihydroxy-4, 4' -dimethoxybenzophenone (benzophenone-6), such as the product sold under the name Helisorb 11 by Norquay; -5-chloro-2 -hydroxybenzophenone :(benzophenone-7); 2,2' -dihydroxy-4-methoxybenzophenone, also known as dioxybenzone or benzophenone-8, such as the product sold under the name Spectra-Sorb UV-24 by American Cyanamid; the disodium salt of 2,2'-dihydroxy-4,4'dimethoxybenzophenone-5, 5' -disulphonic acid or benzophenone-9, such as the product sold under the name Uvinul DS49 by BASF; 2-hydroxy-4-methoxy-4'-methylbenzophenone benzophenone-11, such as the product sold under the name Uvinul M493 by BASF; -2-hydroxy-4-(octyloxy)benzophenone (benzophenone-12).
Among the anthranilates which can be used according to the invention, mention may be made most 10 particularly of menthyl anthranilate, such as the product sold under the name Neo Heliopan MA by the company Haarmann Reimer.
As UV-B screening agents which are particularly used in the context of the present 15 invention, mention may be made of the triazine derivatives described in particular in US patent 4 617 390 and patent applications EP-A-087 098, EP-A-0 517 104, EP-A-0 570 838 and EP-A-0 796 851.
2,4,6-Tris[p-(2'-ethylhexyl-l'-oxycarbonyl)anilino]- 1,3,5-triazine, sold in particular under the trade name "Uvinul T 150" by the company BASF, is known in particular.
Cinnamic acid derivatives such as isopentyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, methyl diisopropylcinnamate, isoamyl 4-methoxycinnamate and diethanolamine 4-methoxycinnamate are also advantageously used.
Among the cinnamic acid derivatives mentioned above, the one most particularly preferred for use according to the present invention is 2-ethylhexyl p-methoxycinnamate, sold in particular under the trade name "Parsol MCX" by the company Givaudan.
Alkyl 2-cyano-3,3-diphenylacrylates can also be used, and preferably octocrylidene sold under the name Uvinul N 539 by the company BASF.
Photoprotective agents which can also advantageously be used are alkyl, ethyl, propyl, octyl or glyceryl para-aminobenzoates or paradimethylaminobenzoates. 3,4'-methylbenzylidenecamphor, 3-benzylidenecamphor, benzylidenecamphor 3,4'trimethylammonium methylsulphate and 15 sulphobenzylidene)camphor and its salts can also be used.
*a.
Photoprotective agents which are most particularly preferred are 2-ethylhexyl p-methoxycinnamate, triazine derivatives, and in particular 20 2 4 6 -tris[p-(2-ethylhexyl-l-acycarbonyl)]anilino- 1,3,5-triazine, salicylates, and in particular methyl or octyl salicylates, para-aminobenzoates or paradimethylaminobenzoates, alkyl 2-cyano-3,3-diphenylacrylate and metal oxide nanopigments, or mixtures thereof.
The cosmetic compositions according to the invention can also contain as photoprotective agents, pigments or nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably 10 nm and 50 nm) of coated or uncoated metal oxides such as, for example, nanopigments of titanium oxide (amorphous or crystallized in rutile and/or anatase form), of iron oxide, of zinc oxide, of zirconium oxide or of cerium oxide, which are all UV photoprotective agents that are well known per se.
Conventional coating agents are, moreover, alumina and/or aluminium stearate. Such coated or uncoated metal oxide nanopigments are described in particular in patent applications EP-A-0 518 772 and EP-A-0 518 773.
The cosmetically acceptable medium preferably consists of water or one or more cosmetically acceptable solvents such as alcohols or 15 water/solvent(s) mixtures, the solvents preferably being C 1
-C
4 alcohols.
Among these alcohols which may be mentioned are ethanol and isopropanol. Ethanol is particularly preferred.
20 The composition of the invention can also contain at least one additive chosen from anionic, cationic, nonionic and amphoteric surfactants, fragrances, screening agents, preserving agents, proteins, vitamins, polymers other than those of the invention, plant, mineral or synthetic oils and any other additive conventionally used in cosmetic compositions.
Needless to say, a person skilled in the art will take care to select the optional compound(s) to be added to the composition according to the invention such that the advantageous properties intrinsically associated with the composition in accordance with the invention are not, or are not substantially, adversely affected by the addition envisaged.
These compositions may be packaged in various forms, in particular in pump-dispenser bottles or in aerosol containers, in order to ensure application of the composition in vaporized form or in the form of a oo0 mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating hair. The oo 15 compositions in accordance with the invention can also be in the form of creams, gels, emulsions, lotions or waxes.
oooo When the composition according to the invention is packaged in aerosol form in order to obtain a lacquer or a mousse, it comprises at least one propellant which may be chosen from volatile hydrocarbons such as n-butane, propane, isobutane and pentane, a halogenated hydrocarbon and mixtures thereof. Carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen or compressed air can also be used as propellant. Mixtures of propellants can also be used.
Dimethyl ether is preferably used.
The propellant is advantageously present in a concentration of between 5% and 90% by weight relative to the total weight of the composition in the aerosol device, and more particularly at a concentrationof between 10% and The compositions in accordance with the invention are particularly suitable for dry or wet hair, as styling products.
The compositions in accordance with the 10 invention can be applied to the skin, the nails, the lips, the hair, the eyebrows and the eyelashes.
oooo The invention will be illustrated more fully with the aid of the non-limiting example which follows.
All the percentages are relative percentages 15 by weight with respect to the total weight of the oooo composition, and a.m. means active material.
o• •owe oooo
EXAMPLE:
Luviflex Silk (BASF)( 1 2 g Uvunul MS 40 1 g Ethanol 20 g AMP qs pH=7 Water qs 100 g Composition A is applied to a lock of 5 g of European natural chestnut hair. After drying, the lock feels soft and is protected against the harmful effects of the sun.
29 Silicone/acrylate copolymer sold by the company BASF (t-butyl acrylate/methacrylic acid/PDMS polyether) It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in the art, in Australia or in any other country.
For the purposes of this specification it will be clearly understood that the word "comprising' means "including but not limited to", and that the word "comprises" has a corresponding meaning.
Claims (8)
1. Cosmetic composition comprising, in a cosmetically acceptable medium, at least one silicone/acrylate copolymer and at least one photoprotective agent, the silicone/acrylate copolymer being obtained by radical-mediated polymerization of at least one ethylenically unsaturated monomer in the presence of at least one silicone derivative (b) 10 comprising oxyalkylene groups.
2. Composition according to Claim 1, characterized in that the monomer corresponds to formula (Ia): X-C-CR =CHR 6 (Ia) 0 *o in which: X is chosen from the group comprising OH, OM, ORE, NH 2 NHR 8 and N(R 8 2 M is a cation chosen from Na K Mg+, NH 4 alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium; the radicals R 8 may be identical or different and are chosen from the group comprising hydrogen, linear or branched Ci to C 4 o alkyl groups, mono- or polyhydroxylated C 1 to C 40 alkyl groups, optionally substituted with one or more alkoxy, amino or carboxyl groups, hydroxylated polyethers, and N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, hydroxypropyl, methoxypropyl and ethoxypropyl groups; R 7 and R 6 are chosen, independently of each other, from the group comprising hydrogen, linear or branched C 1 to C 8 alkyl groups, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl groups, and CN, COOH and COOM groups. 10 3. Cosmetic composition according to Claim 1, characterized in that the silicone derivative (b) corresponds to the formula below: S.. in which formula 2 R is chosen from CH 3 and the group R R is chosen from hydrogen, CH 3 and the R 4 is chosen from hydrogen, CH 3 and the groups FR R S-0- -&i.-CH3 -te _dc R 1 -'x contain amino, carboxyl or sulphonate groups, and if
9.o. c=0, R 6 is the anion of an inorganic acid; 9 9 9. 5 the radicals R may be identical or o. different and are chosen from Ci to C 20 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the t.4. vformula below: 2aCa 9. n is an integer between l and 6, 999 0 9999 x and y are integers chosen such that the molecular weight of the polysiloxane is between 300 and 30,000, a and b are integers between 0 and 50, and c is 0 or 1. 4. Composition according to Claim 1, characterized in that the monomer is chosen from C 1 to C 40 vinyl and allyl esters, linear C 3 to C 40 carboxylic acids or C 3 to C 40 carboxycyclic acids, vinyl or allyl haldides, vinyllactams, preferably vinylpyrrolidone and vinylcaprolactam, heterocyclic compounds substituted with vinyl or allyl groups, preferably vinylpyridine, vinyloxazoline and allylpyridine, N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds, such as styrene or isoprene, and acrylic or methacrylic acid derivatives quaternized with epichlorohydrin. 10 5. Composition according to Claim 1, characterized in that the monomer is chosen from the group comprising acrylic, methacrylic and ethacrylic acid; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl acrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl methacrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and **decyl ethacrylate; 2,3-dihydroxypropyl acrylate; 2,3-dihydroxypropyl methacrylate; 2-dihydroxyethyl acrylate; hydroxypropyl acrylate; 2-hydroxyethyl methacrylate; 2-hydroxyethyl ethacrylate; 2-methoxyethyl acrylate; 2-ethoxyethyl methacrylate; 2-ethoxyethyl ethacrylate; hydroxypropyl methacrylate; glyceryl monoacrylate; glyceryl monomethacrylate; polyalkylene glycol (meth)acrylates, unsaturated sulphonic acids, acrylamide, methacrylamide, ethacrylamide, N,N-dimethylacrylamide, N-ethyl- acrylamide, N-ethylmethacrylamide, 1-vinylimidazole, N,N-dimethylaminoethyl (meth)acrylate, maleic acid, fumaric acid, maleic anhydride and its monoesters, crotonic acid, itaconic acid, vinyl ethers, vinylformamide, vinylamine, vinylpyridine, vinylimidazole, vinylfuran, styrene, styryl sulphonate and allyl alcohol, and mixtures thereof. 6. Composition according to any one of the preceding claims, characterized in that the silicone derivatives are chosen from dimethicone copolyols *o 10 and silicone surfactants. 7. Composition according to any one of the .preceding claims, characterized in that it comprises, as a relative percentage by weight, from 0.1% to 20% of silicone/acrylate copolymer, and more preferably from 0.5% to 10% of this copolymer. 8. Composition according to any one of Claims 1 to 7, characterized in that the photoprotective agent is chosen from: dibenzoylmethane derivatives; the UV-A-active screening agents of formula I below: R 7 R in which: R 7 and R 9 which may be identical or different, denote a hydrogen, a halogen, an OH radical, a saturated or unsaturated, linear or branched Ci-Clo alkyl radical; a saturated or unsaturated, linear or branched C 1 -Clo alkoxy radical or an HSO 3 group; R 10 denotes hydrogen or HSO 3 R 8 denotes hydroxyl; a group OR 1 in which R 11 denotes a saturated or unsaturated, linear or branched Ci-Cio alkyl radical; or a group of the 10 following structure: 12 in which R 12 denotes hydrogen or HSO 3 or alternatively a group of the following formula: COOR 13 1 :::14 or alternatively a group of the following formula: N -R 1 16 in which: Z denotes an oxygen atom or an -NH- radical; R 13 R 14 R 15 and R 16 which may be identical or different, denote a hydrogen, a halogen, an OR radical, a saturated or unsaturated, linear or branched C1-Clo alkyl radical; a saturated or unsaturated, linear or branched CI-Clo alkoxy radical or an HS0 3 group; the UV-A-active screening agents of the benzimidazole or benzoxazole type of formula (II) 10 below: R 1 18 in which: W denotes an oxygen atom or an -NH- radical, 15 R 17 denotes hydrogen or HSO 3 R 8 I denotes a linear or branched alkoxy radical containing from 1 to 10 carbon atoms approximately or a group of the following formula: IN I R in which Y represents an oxygen atom or an -NH- radical and R 19 denotes hydrogen or HSO 3 R 19 denotes hydrogen or HSO 3 benzophenone derivatives such as those of formula (III) below: R OH 24 23 "OR R 22 F1 in which: R 20 denotes hydrogen or a saturated or unsaturated, linear or branched Ci-Cio alkyl radical; R 21 and R 22 which may be identical or different, denote a hydrogen, a halogen, an OH radical, a saturated or unsaturated, linear or branched Ci-Cio 1. 10 alkyl radical; a saturated or unsaturated, linear or branched Ci-C 10 alkoxy radical or an HSO 3 group; R. 23 denotes hydrogen; OH; a saturated or unsaturated, linear or branched Ci-Cio alkyl radical or a saturated or unsaturated, linear or branched Ci-Cio 15 alkoxy radical; R 24 denotes OH, a hydrogen atom or a saturated or unsaturated, linear or branched Ci-Clo alkyl radical; silane derivatives or polyorganosiloxanes containing a benzophenone group; anthranilates; benzotriazoles and benzotriazole silicones; mixtures thereof. 9. Composition according to any one of Claims 1 to 7, characterized in that the photoprotective agent is chosen from cinnamic acid derivatives, 2-ethylhexyl p-methoxycinnamate, triazine derivatives, and in particular 2,4,6-tris[p-(2- salicylates, and in particular methyl or octyl salicylates, para-aminobenzoates or para- dimethylaminobenzoates, alkyl 2-cyano-3,3-diphenyl- 10 acrylate and metal oxide nanopigments, or mixtures *0 thereof.
10. Composition according to any one of Claims 1 to 7, characterized in that the photoprotective agent is chosen from 3,4'-methyl- benzylidenecamphor, 3-benzylidenecamphor, benzylidenecamphor 3,4'-trimethylammonium methylsulphate and 3-(4'-sulphobenzylidene)camphor and its salts.
11. Composition according to any one of the preceding claims, characterized in that it also contains at least one additive chosen from anionic, cationic, nonionic and amphoteric surfactants, fragrances, preserving agents, proteins, vitamins, polymers other than those of the invention, and plant, mineral or synthetic oils.
12. Process for holding or shaping the hairstyle, characterized in that it uses a composition in accordance with any one of Claims 1 to 11.
13. Use of a composition according to any one of Claims 1 to 11, for the manufacture of a cosmetic product, in particular a hair product.
14. Use according to any one of Claims 1 to 11, for the skin, the nails, the lips, the hair, the eyebrows and the eyelashes. Dated this 5th day of September 2000 L'OREAL By their Patent Attorneys GRIFFITH HACK :o Fellows Institute of Patent and Trade Mark Attorneys of Australia So 6 0* O* S
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9911593A FR2798587B1 (en) | 1999-09-16 | 1999-09-16 | COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE / ACRYLATE COPOLYMER AND AT LEAST ONE PHOTOPROTECTIVE AGENT |
FR9911593 | 1999-09-16 |
Publications (2)
Publication Number | Publication Date |
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AU5648400A true AU5648400A (en) | 2001-03-22 |
AU750044B2 AU750044B2 (en) | 2002-07-11 |
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Application Number | Title | Priority Date | Filing Date |
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AU56484/00A Ceased AU750044B2 (en) | 1999-09-16 | 2000-09-05 | Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one photoprotective agent |
Country Status (13)
Country | Link |
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EP (2) | EP1084696B1 (en) |
JP (2) | JP2001131017A (en) |
KR (1) | KR100364308B1 (en) |
CN (1) | CN1295832A (en) |
AT (1) | ATE255876T1 (en) |
AU (1) | AU750044B2 (en) |
BR (1) | BR0004322A (en) |
CA (1) | CA2319930C (en) |
DE (1) | DE60007046T2 (en) |
ES (1) | ES2211474T3 (en) |
FR (1) | FR2798587B1 (en) |
PL (1) | PL342563A1 (en) |
RU (1) | RU2200536C2 (en) |
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BR112019011780B1 (en) | 2016-12-12 | 2023-03-07 | Clariant International Ltd | POLYMER COMPRISING CARBON FROM BIOLOGICAL MATERIAL, ITS OBTAINMENT PROCESS AND ITS USE |
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WO2019115478A1 (en) | 2017-12-11 | 2019-06-20 | Clariant International Ltd | Composition for inhibiting micro-organisms |
US11753379B2 (en) | 2018-05-30 | 2023-09-12 | Clariant International Ltd | Process for forming 2-hydroxypyridine-1-oxide or derivatives thereof |
KR102518737B1 (en) | 2018-07-05 | 2023-04-06 | 클라리언트 인터내셔널 리미티드 | Antimicrobial Complex Composition Containing Glycerol Derivatives and Bicyclic Compounds |
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EP4008406A1 (en) | 2020-12-07 | 2022-06-08 | Clariant International Ltd | Cosmetic composition based on acroyl taurate type polymers |
JP2024512291A (en) | 2021-03-02 | 2024-03-19 | クラリアント・インターナシヨナル・リミテツド | antimicrobial composition |
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WO2024074409A1 (en) | 2022-10-06 | 2024-04-11 | Clariant International Ltd | Combination comprising a glucamide and a co-emulsifier |
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US5240695A (en) * | 1988-02-11 | 1993-08-31 | L'oreal | Use of 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid or its salts for protecting the hair against environmental attacking agents, and especially against light and process for protecting the hair using the compound |
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FR2735689B1 (en) * | 1995-06-21 | 1997-08-01 | Oreal | COMPOSITION COMPRISING A DISPERSION OF POLYMER PARTICLES IN A NON-AQUEOUS MEDIUM |
FR2746005B1 (en) * | 1996-03-14 | 1998-04-30 | COSMETIC COMPOSITION COMPRISING AN ACION ACRYLIC POLYMER AND OXYALKYLENE SILICONE | |
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US5985294A (en) * | 1997-11-05 | 1999-11-16 | The Procter & Gamble Company | Personal care compositions |
CN1194024C (en) | 1999-08-26 | 2005-03-23 | 巴斯福股份公司 | Cosmetic and/or pharmaceutical preparations with polymers containing polysiloxanes and the uses thereof |
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1999
- 1999-09-16 FR FR9911593A patent/FR2798587B1/en not_active Expired - Fee Related
-
2000
- 2000-08-28 EP EP00402375A patent/EP1084696B1/en not_active Expired - Lifetime
- 2000-08-28 ES ES00402375T patent/ES2211474T3/en not_active Expired - Lifetime
- 2000-08-28 DE DE60007046T patent/DE60007046T2/en not_active Expired - Lifetime
- 2000-08-28 AT AT00402375T patent/ATE255876T1/en active
- 2000-08-28 EP EP03290733A patent/EP1321127A3/en not_active Ceased
- 2000-09-05 AU AU56484/00A patent/AU750044B2/en not_active Ceased
- 2000-09-14 BR BR0004322-2A patent/BR0004322A/en not_active IP Right Cessation
- 2000-09-14 CA CA002319930A patent/CA2319930C/en not_active Expired - Fee Related
- 2000-09-14 JP JP2000280637A patent/JP2001131017A/en not_active Withdrawn
- 2000-09-15 RU RU2000123757/14A patent/RU2200536C2/en not_active IP Right Cessation
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- 2000-09-16 KR KR1020000054484A patent/KR100364308B1/en not_active IP Right Cessation
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2004
- 2004-08-03 JP JP2004227169A patent/JP2004323535A/en active Pending
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CA2319930C (en) | 2006-05-23 |
ES2211474T3 (en) | 2004-07-16 |
CN1295832A (en) | 2001-05-23 |
AU750044B2 (en) | 2002-07-11 |
FR2798587A1 (en) | 2001-03-23 |
EP1084696B1 (en) | 2003-12-10 |
FR2798587B1 (en) | 2001-11-30 |
PL342563A1 (en) | 2001-03-26 |
CA2319930A1 (en) | 2001-03-16 |
ATE255876T1 (en) | 2003-12-15 |
EP1084696A1 (en) | 2001-03-21 |
KR20010030422A (en) | 2001-04-16 |
BR0004322A (en) | 2001-04-10 |
DE60007046T2 (en) | 2004-07-08 |
EP1321127A2 (en) | 2003-06-25 |
JP2001131017A (en) | 2001-05-15 |
DE60007046D1 (en) | 2004-01-22 |
JP2004323535A (en) | 2004-11-18 |
RU2200536C2 (en) | 2003-03-20 |
KR100364308B1 (en) | 2002-12-12 |
EP1321127A3 (en) | 2003-07-02 |
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