WO2002019979A2 - COMPOSITION FILTRANTE CONTENANT UN DERIVE DU DIBENZOYLMETHANE ET UN DIMERE DERIVE D'α-ALKYLSTYRENE, PROCEDE DE PHOTOSTABILISATION - Google Patents
COMPOSITION FILTRANTE CONTENANT UN DERIVE DU DIBENZOYLMETHANE ET UN DIMERE DERIVE D'α-ALKYLSTYRENE, PROCEDE DE PHOTOSTABILISATION Download PDFInfo
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- WO2002019979A2 WO2002019979A2 PCT/FR2001/002655 FR0102655W WO0219979A2 WO 2002019979 A2 WO2002019979 A2 WO 2002019979A2 FR 0102655 W FR0102655 W FR 0102655W WO 0219979 A2 WO0219979 A2 WO 0219979A2
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- 239000000203 mixture Substances 0.000 title claims abstract description 74
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 10
- 230000003019 stabilising effect Effects 0.000 title 1
- 230000005855 radiation Effects 0.000 claims abstract description 18
- 239000002537 cosmetic Substances 0.000 claims abstract description 17
- 239000000539 dimer Substances 0.000 claims abstract description 15
- 239000004904 UV filter Substances 0.000 claims abstract description 12
- 210000004209 hair Anatomy 0.000 claims abstract description 9
- 230000004224 protection Effects 0.000 claims abstract description 7
- 230000000699 topical effect Effects 0.000 claims abstract description 4
- -1 alkyl radical Chemical class 0.000 claims description 101
- 150000003254 radicals Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 210000003491 skin Anatomy 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000000839 emulsion Substances 0.000 claims description 11
- 239000006185 dispersion Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000499 gel Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 150000007942 carboxylates Chemical group 0.000 claims description 7
- 239000006071 cream Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 210000002615 epidermis Anatomy 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229960000655 ensulizole Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 4
- 229960001173 oxybenzone Drugs 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical group C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 claims description 3
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical class OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 claims description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 3
- 150000001556 benzimidazoles Chemical class 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 150000001565 benzotriazoles Chemical class 0.000 claims description 3
- 229940068171 ethyl hexyl salicylate Drugs 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 235000013336 milk Nutrition 0.000 claims description 3
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- 210000004080 milk Anatomy 0.000 claims description 3
- 229960000601 octocrylene Drugs 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 229960000368 sulisobenzone Drugs 0.000 claims description 3
- 150000003918 triazines Chemical class 0.000 claims description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
- KHNVQXPXLJIGFS-UHFFFAOYSA-N 7-[(6-hydroxy-5-phenyl-2H-benzotriazol-4-yl)methyl]-6-phenyl-2H-benzotriazol-5-ol Chemical class C=1C=CC=CC=1C=1C(O)=CC=2NN=NC=2C=1CC(C=1N=NNC=1C=C1O)=C1C1=CC=CC=C1 KHNVQXPXLJIGFS-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002535 acidifier Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 229940061720 alpha hydroxy acid Drugs 0.000 claims description 2
- 150000001280 alpha hydroxy acids Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000002610 basifying agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229960000979 drometrizole Drugs 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000003974 emollient agent Substances 0.000 claims description 2
- 210000004709 eyebrow Anatomy 0.000 claims description 2
- 210000000720 eyelash Anatomy 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000000077 insect repellent Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003605 opacifier Substances 0.000 claims description 2
- 235000011837 pasties Nutrition 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 239000003380 propellant Substances 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000003890 substance P antagonist Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000002562 thickening agent Substances 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
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 239000002518 antifoaming agent Substances 0.000 claims 1
- 229910000420 cerium oxide Inorganic materials 0.000 claims 1
- DRVWBEJJZZTIGJ-UHFFFAOYSA-N cerium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Ce+3].[Ce+3] DRVWBEJJZZTIGJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000003711 photoprotective effect Effects 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000000475 sunscreen effect Effects 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 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 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- HEAHZSUCFKFERC-IWGRKNQJSA-N [(2e)-2-[[4-[(e)-[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-IWGRKNQJSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000008346 aqueous phase Substances 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
- 238000004061 bleaching Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229940120503 dihydroxyacetone Drugs 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000000176 photostabilization Effects 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- OIQXFRANQVWXJF-ACCUITESSA-N (2e)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C\C1=CC=CC=C1 OIQXFRANQVWXJF-ACCUITESSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 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 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KKJKXQYVUVWWJP-JLHYYAGUSA-N 4-[(e)-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C\C1=CC=C(S(O)(=O)=O)C=C1 KKJKXQYVUVWWJP-JLHYYAGUSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- OIVKTEDNJRKDRC-UHFFFAOYSA-N CC(C)c(cc1)ccc1C(CC(c(cc1)ccc1OC)=O)=O Chemical compound CC(C)c(cc1)ccc1C(CC(c(cc1)ccc1OC)=O)=O OIVKTEDNJRKDRC-UHFFFAOYSA-N 0.000 description 1
- BDVJIVPBVRZTNI-UHFFFAOYSA-N CC(c(cc1)ccc1OBOc(cc1)ccc1C(C)=C(C#N)C#N)=C(C#N)C#N Chemical compound CC(c(cc1)ccc1OBOc(cc1)ccc1C(C)=C(C#N)C#N)=C(C#N)C#N BDVJIVPBVRZTNI-UHFFFAOYSA-N 0.000 description 1
- GQDRGBVPGCYTNU-UHFFFAOYSA-N CCC1C(CC)CCCC1 Chemical compound CCC1C(CC)CCCC1 GQDRGBVPGCYTNU-UHFFFAOYSA-N 0.000 description 1
- SMAKEJNOUFLEEJ-UHFFFAOYSA-N CCC1CCC(CC)CC1 Chemical compound CCC1CCC(CC)CC1 SMAKEJNOUFLEEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 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
- 206010015150 Erythema Diseases 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 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 description 1
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 230000004075 alteration Effects 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
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229960001716 benzalkonium Drugs 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229940111759 benzophenone-2 Drugs 0.000 description 1
- 229940079894 benzophenone-9 Drugs 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
- 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 1
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- 229930008380 camphor Natural products 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GLCJMPWWQKKJQZ-UHFFFAOYSA-L disodium;2-[4-(4,6-disulfonato-1h-benzimidazol-2-yl)phenyl]-1h-benzimidazole-4,6-disulfonate;hydron Chemical compound [Na+].[Na+].C1=C(S(O)(=O)=O)C=C2NC(C3=CC=C(C=C3)C3=NC4=C(C=C(C=C4N3)S(=O)(=O)O)S([O-])(=O)=O)=NC2=C1S([O-])(=O)=O GLCJMPWWQKKJQZ-UHFFFAOYSA-L 0.000 description 1
- HUVYTMDMDZRHBN-UHFFFAOYSA-N drometrizole trisiloxane Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CC(C)CC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O HUVYTMDMDZRHBN-UHFFFAOYSA-N 0.000 description 1
- HEAHZSUCFKFERC-UHFFFAOYSA-N ecamsule Chemical compound CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)C2=CC(C=C1)=CC=C1C=C1C(=O)C2(CS(O)(=O)=O)CCC1C2(C)C HEAHZSUCFKFERC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960004881 homosalate Drugs 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000001333 moisturizer Effects 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Natural products OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 230000004051 prolonged sun exposure Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 231100000075 skin burn Toxicity 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 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 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
-
- 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
- A61Q5/02—Preparations for cleaning the hair
Definitions
- the invention relates to a cosmetic or dermatological composition for topical use, in particular for the photoprotection of the skin and hair, characterized in that it comprises at least in a cosmetically acceptable carrier:
- the invention relates to a new method for improving the stability of at least one dibenzoylmethane derivative with respect to UV radiation, consisting in associating with said dibenzoylmethane derivative an effective amount of at least one dimer derived from ⁇ -special alkylstyrene
- UV-A rays with wavelengths between 320 and 400 nm, which cause browning of the skin, are capable of inducing an alteration of the latter, in particular in the case of skin. sensitive or skin continuously exposed to solar radiation.
- UV-A rays cause in particular a loss of elasticity in the skin and the appearance of wrinkles, leading to premature skin aging. They promote the triggering of the erythematous reaction or amplify this reaction in certain subjects and can even be the cause of phototoxic or photoallergic reactions.
- UV-A rays For aesthetic and cosmetic reasons such as the conservation of the natural elasticity of the skin for example, more and more people wish to control the effect of UV-A rays on their skin. It is therefore desirable to also filter UV-A radiation.
- UV-A filters a particularly interesting family of UV-A filters is currently constituted by dibenzoylmethane derivatives, and in particular 4- (ter.-butyl) 4'-methoxy dibenzoylmethane, which indeed have a strong intrinsic absorption power.
- dibenzoylmethane derivatives which are now products well known per se as active filters in UV-A, are described in particular in French patent applications FR-A-2326405 and FR-A-2440933, as well as in European patent application EP-A-0114607; 4- (ter.-butyl) 4'-methoxy dibenzoyl-methane is also currently offered for sale under the trade name "PARSOL 1789" by the company HOFFMANN LAROCHE.
- the dibenzoylmethane derivatives are products relatively sensitive to ultraviolet radiation (especially UV-A), that is to say, more precisely, that they have an annoying tendency to degrade more or less quickly. under the action of the latter.
- UV-A ultraviolet radiation
- this substantial lack of photochemical stability of the dibenzoylmethane derivatives in the face of the ultraviolet radiation to which they are by nature intended to be subjected does not make it possible to guarantee constant protection during prolonged sun exposure, so that applications repeated at intervals of time Regular and close together must be performed by the user to obtain effective protection of the skin against UV rays.
- the Applicant has now discovered, surprisingly, that by combining the above-mentioned dibenzoylmethane derivatives with a quantity effective of at least one dimer derived from a particular ⁇ -alkylstyrene which will be defined later, it was possible to substantially and remarkably improve the photochemical stability (or photostability) of these same dibenzoylmethane derivatives.
- a new cosmetic or dermatological composition for topical use, in particular for the photoprotection of the skin and hair, characterized in that it comprises at less in a cosmetically acceptable support:
- Another object of the invention is a new process for stabilizing dibenzoylmethane derivatives with respect to UV radiation (wavelengths between 280 nm and 400 nm approximately), in particular solar radiation, characterized by the fact that it consists in associating with said dibenzoylmethane derivatives an effective amount of at least one dimer derived from ⁇ -alkylstyrene of formula (I) defined below.
- effective amount of dimer derived from ⁇ -alkylstyrene is meant an amount sufficient to obtain a significant and significant improvement in the photostability of the dibenzoylmethane derivative (s) of the photoprotective cosmetic composition.
- This minimum quantity of photostabilizing agent to be used which can vary depending on the nature of the cosmetically acceptable support chosen for the composition, can be determined without any difficulty by means of a conventional test for measuring photostability, such as that given in the examples below.
- the present invention also finally relates to the use of a dimer derived from ⁇ -alkylstyrene of formula (I) defined below in the preparation of a cosmetic or dermatological composition comprising at least one derivative of dibenzoylmethane in order to improve the stability vis-à-vis UV rays of said dibenzoylmethane derivative contained.
- a dimer derived from ⁇ -alkylstyrene of formula (I) defined below in the preparation of a cosmetic or dermatological composition comprising at least one derivative of dibenzoylmethane in order to improve the stability vis-à-vis UV rays of said dibenzoylmethane derivative contained.
- dimeric compounds derived from ⁇ -alkylstyrene in accordance with the invention correspond to the following formula (I):
- - R 1 and R 2 identical or different, denote hydrogen, OH, NH 2 , a C 1 -C 1 2 alkyl radical, linear or branched; alkoxy C1-C 12, linear or branched; a linear or branched CrC 12 monoalkylamino radical; a linear or branched C 1 -C 12 dialkylamino radical or a water-solubilizing substituent chosen from a carboxylate group, a sulfonate group or an ammonium residue; - R 3 and R 4 , identical or different, denote a group COOR 6 , COR 6 , CONR 6 R 7 or CN;
- R 5 denotes a linear or branched C-1-C12 alkyl radical
- R 6 and R 7 identical or different denote hydrogen, a linear or branched C1-C12 alkyl radical; a linear or branched C2-C10 alkenyl radical; a C3-C10 cycloalkyl radical branched or not; a branched or unbranched C 3 -C 10 cycloalkenyl; C6-C18 aryl, C 4 -C heteroaryl; said cycloalkyl, cycloalkenyl or aryl groups which may contain one or more substituents chosen from halogens, a cyano group, a nitro group, an amino group, a Cr C4 monoalkylamino radical, a C ⁇ -C -dialkylamino radical, a hydroxy group, a radical C- ⁇ -C-4-alkyl, a C ⁇ -C alkoxy radical; said cycloalkyl groups, cycloalkenyl possibly comprising one or more heteroatoms (for example O, N,
- - A denotes O, S or a group NR 8 ;
- R 8 denotes hydrogen or a C 1 -C 12 alkyl radical, linear or branched;
- B denotes a linear or branched C 1 -C 12 alkylene radical which may contain one or more substituents chosen from hydroxy, OC-i-C ⁇ -acyl, NH 2 ,
- NH-Ci-Ce-alkyl NH-C ⁇ -C 6 .acyl, CN, COOH, COO-C ⁇ -C 6 -acyl; a C -C ⁇ 2 cycloalkylene radical, branched or not; a C 8 -C 22 aralkylene radical; a C9-C21 monooxoaralkylene radical; a group [X] n -Y-;
- At least two of the radicals R 1 , R 2 and R 8 can together form a 5 or 6-membered ring with the benzene ring to which they are linked.
- - X denotes a group -CH 2 -CH 2 -Z-, -CH 2 CH 2 CH 2 Z-, -CH (CH 3 ) -CH 2 -Z-,
- -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -Z- -CH 2 -CH (CH 2 CH 3 ) -Z-
- - Y denotes a group -CH 2 -CH 2 -, -CH2CH2CH2-, -CH (CH 3 ) -CH 2 -, -CH 2 -CH 2 -CH 2 -CH2-, -CH -CH (CH 2 CH 3 ) -;
- - Z denotes O or S
- - n varies from 1 to 150.
- C 1 to C 2 alkyl radicals for the radicals R 1 , R 2 , R 6 , R 8 and B, there may be mentioned for example: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2 -methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1- dimethylpropyl, 1, 2-dimethylpropyl , 1-methylpentyle, 2-methylpentyle, 3-methylpentyle, 4-methylpentyle, 1,1-dimethylbutyl, 1,2-dimethylbutyie, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3 -dimethylbutyl, 1- eth
- alkenyl groups C2-C 10 for R 6 and R 7, there may be mentioned for example: ethenyl, n-propenyl, 1-methylethenyl, n-butenyl, 1-methyl-propenyl, 2-methyl propenyl, 1!
- Cycloalkyl radicals such as C 3 -C 10 for R 6 and R 7, there may be mentioned for example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyle, 1-butyl-cyclopropyl , 1-pentylcyclopropyle, 1-methyl-1-butylcyclopropyle, 1, 2-dimethyl-cyclypropyl, 1-methyl-2-ethylcyclopropyle, cyclooctyle, cyclononyl or cyclodecyl.
- cyclobutenyl As C 3 -C 10 cycloalkylene radicals having one or more double bonds, for the radicals R 6 and R 7 , there may be mentioned: cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, 1, 3-cyclohexadienyl, 1, 4-cyclohexadienyl, cycloheptenyl , cycloheptatrienyl, cyclooctenyl, 1,5-cyclooctadienyl, cyclooctetraenyl, cyclononenyl or cyclodecenyl.
- C 1 -C 12 alkoxy radicals for the radicals R 1 and R 2 there may be mentioned: methoxy, n-propoxy, 1-methylpropoxy, n-pentoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-methyl-1 -ethylpropoxy, octoxy, ethoxy, n-propoxy, n-butoxy, 2-methylpropoxy, 1, 1-dimethylpropoxy, hexoxy, heptoxy, 2-ethylhexoxy.
- the aryl groups for the radicals R 6 and R 7 are more particularly phenyl, methoxyphenyl or naphthyl.
- the water-soluble groups designated by the radicals R 1 and R 2 are, for example, carboxylate groups, sulfonates and more particularly their salts with physiologically acceptable cations such as the alkali metal salts or the trialkylammonium salts such as the tri (hydroxyalkyl) salts ammonium or 2-methylpropan-1-ol-2-ammonium. Mention may also be made of ammonium groups such as alkylammoniums and their salified forms with physiologically acceptable anions.
- R 1 and R 2 identical or different, denote hydrogen, a C1-Cs alkyl radical, a C1-Cs alkoxy radical, a water-solubilizing substituent chosen from a carboxylate group, a sulfonate group or an ammonium residue;
- R 3 and R 4 identical or different, denote a COOR 6 or CN group;
- R 5 denotes a C1-C6 alkyl radical
- R 6 denotes a C- ⁇ -C 2 alkyl radical
- - A denotes O
- - B denotes a C- ⁇ -C ⁇ 2 alkylene radical, a C 4 -C- ⁇ 2 cycloalkylene radical, a Cs-C-22 aralkylene radical, a group [X] n -Y-;
- - X denotes a group -CH 2 -CH 2 -0-, -CH 2 CH 2 CH 2 0-, -CH (CH 3 ) -CH 2 -0-,
- - Y denotes a group -CH 2 -CH 2 -, -CH2CH 2 CH 2 -, -CH (CH 3 ) -CH 2 -, -CH2-CH2-CH2-, -CH2-CH (CH2CH 3 ) - ;
- - n varies from 1 to 20.
- R 1 and R 2 identical or different, denote hydrogen, an alkyl radical in
- C4-C8 a C 4 -C 6 alkoxy radical, a water-solubilizing substituent chosen from a carboxylate group, a sulfonate group or an ammonium residue;
- R 3 and R 4 denote a CN group
- R 5 an alkyl radical in CrC 6 ;
- - A denotes O;
- - B denotes a C1-C12 alkylene radical, a group [X] n -Y-;
- R 8 denotes hydrogen or a C 1 -C 1 2 alkyl radical
- - X denotes a group -CH 2 -CH 2 -O- or -CH (CH 3 ) -CH 2 -O-,
- - Y denotes a group -CH 2 -CH 2 - or -CH (CH 3 ) -CH 2
- - n varies from 1 to 20.
- R 5 is a CC 6 alkyl radical and more particularly methyl
- B denotes a C C 2 alkylene radical.
- the compounds of formula (I) are generally present in the composition of the invention in proportions of between 0.1% and 20% by weight, preferably between 0.5% and 10% by weight, relative to the total weight of composition.
- the dibenzoylmethane derivatives intended to be photostabilized in the context of the present invention are products already well known per se and described in particular in the aforementioned documents FR2326405, FR2440933 and EP01 14607, documents whose teachings are, as far as touches the very definition of these products, fully included for reference in this description.
- Another preferred dibenzoylmethane derivative according to the present invention is 4-isopropyl-dibenzoylmethane, a filter sold under the name of "EUSOLEX 8020" by the company MERCK, and corresponding to the following developed formula: o o
- the dibenzoylmethane derivative (s) may be present in the compositions in accordance with the invention, or in the compositions intended to be stabilized in accordance with the process of the invention, at contents which are generally between 0.1% and 20% by weight, and preferably at contents of between 0.5% and 10% by weight, relative to the total weight of the composition.
- compositions in accordance with the invention may also comprise other complementary organic UV filters active in UVA and / or UVB (absorbers), water-soluble or liposoluble or else insoluble in the cosmetic solvents commonly used.
- the additional organic UV filters are chosen in particular from anthranilates; salicylic derivatives, camphor derivatives; benzophenone derivatives; triazine derivatives such as those described in patent applications US4367390, US4,724,137, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469 and EP933376, EP507691, EP507692, EP790243, EP944624; derivatives of ⁇ , ⁇ '-diphenylacrylate; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imadazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US 2,463,264; p-aminobenzoic acid derivatives (PABA); the derivatives of methylene bis- (hydroxyphenyl benzotriazole) as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 19726184 and EP89
- Salicylic derivatives - Homosalate sold under the name "EUSOLEX HMS” by RONA / EM INDUSTRIES,
- Dipropyleneglycol Salicylate sold under the name "DIPSAL” by SCHER
- - TEA Salicylate sold under the name "NEO HELIOPAN TS” by HAARMANN and REIMER
- UVINUL 400 Benzophenone-1 sold under the trade name "UVINUL 400" by BASF
- UVINUL D50 Benzophenone-2 sold under the trade name "UVINUL D50" by BASF
- UVINUL M40 Benzophenone-3 or Oxybenzone, sold under the trade name "UVINUL M40" by BASF,
- UVINUL MS40 Benzophenone-4 sold under the trade name "UVINUL MS40" by BASF
- UVINUL DS-49 Benzophenone-9 sold under the trade name UVINUL DS-49 "by BASF,
- UVINUL T150 - Diethylhexyl Butamido Triazone sold under the trade name "UVASORB HEB” by SIGMA 3V
- UVASORB HEB Diethylhexyl Butamido Triazone sold under the trade name "UVASORB HEB” by SIGMA 3V
- Anthranilic derivatives - Menthyl anthranilate sold under the commercial name “NEO HELIOPAN MA” by HAARMANN and REIMER,
- the more particularly preferred complementary organic UV filters are chosen from the following compounds:
- the cosmetic compositions according to the invention may also contain pigments or else nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of metal oxides coated or not as for example of titanium oxide nanopigments (amorphous or crystallized in rutile form and / or anatase), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se. Conventional coating agents are moreover alumina and / or aluminum stearate. Such metallic oxide nanopigments, coated or uncoated, are in particular described in patent applications EP-A-0518772 and EP-A-0518773.
- compositions according to the invention may also contain artificial tanning and / or browning agents for the skin (self-tanning agents), such as for example dihydroxyacetone (DHA).
- artificial tanning and / or browning agents for the skin such as for example dihydroxyacetone (DHA).
- DHA dihydroxyacetone
- compositions of the invention may also comprise conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti-free radical agents, opacifiers, stabilizers , the emollients, silicones, ⁇ -hydroxy acids, defoamers, moisturizers, vitamins, insect repellents, perfumes, preservatives, surfactants, anti-inflammatories, substance P antagonists, fillers , polymers, propellants, basifying or acidifying agents, dyes or any other ingredient usually used in cosmetics, in particular for the manufacture of sunscreen compositions in the form of emulsions.
- conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti-free radical agents, opacifiers, stabilizers , the emollients, silicones, ⁇ -hydroxy acids, defoamers, moisturizers, vitamins, insect repel
- the fatty substances can consist of an oil or a wax or their mixtures, and they also include fatty acids, fatty alcohols and fatty acid esters, linear or cyclic such as derivatives of benzoic acid, trimellitic and hydroxy benzoic acid.
- the oils can be chosen from animal, vegetable, mineral or synthetic oils and in particular from vaseline oil, paraffin oil, silicone oils, volatile or not, isoparaffins, polyolefins, fluorinated oils and perfluorinated.
- the waxes can be chosen from animal, fossil, vegetable, mineral or synthetic waxes known per se.
- organic solvents mention may be made of lower alcohols and polyols.
- compositions of the invention can be prepared according to techniques well known to those skilled in the art, in particular those intended for the preparation of emulsions of the oil-in-water or water-in-oil type.
- compositions can be in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / O or W / O / W) such as a cream, a milk, a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
- the aqueous phase thereof may comprise a nonionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins. J. Mol. Biol. 13, 238 (1965), FR2315991 and FR2416008).
- the cosmetic composition of the invention can be used as a composition for protecting the human epidermis or the hair against ultraviolet rays, as a sunscreen composition or as a make-up product.
- the cosmetic composition according to the invention when used for the protection of the human epidermis against UV rays, or as an antisun composition, it may be in the form of a suspension or of dispersion in solvents or fatty substances, in the form of nonionic vesicular dispersion or alternatively in the form of an emulsion, preferably of the oil-in-water type, such as a cream or a milk, in the form of an ointment, gel, cream gel, solid stick, powder, stick, aerosol foam or spray.
- the cosmetic composition according to the invention when used for protecting the hair against UV rays, it can be in the form of a shampoo, lotion, gel, emulsion, nonionic vesicular dispersion and constitute, for example, a composition to rinse, apply before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, composition for perming or straightening, coloring or bleaching the hair.
- a shampoo, lotion, gel, emulsion, nonionic vesicular dispersion constitute, for example, a composition to rinse, apply before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, composition for perming or straightening, coloring or bleaching the hair.
- composition When the composition is used as an eyelash, eyebrow or skin makeup product, such as epidermis treatment cream, foundation, lipstick stick, eyeshadow, blush, mascara or liner also called “eyeliner", it can be in solid or pasty form, anhydrous or aqueous, such as oil-in-water or water-in-oil emulsions, nonionic vesicular dispersions or even suspensions.
- the aqueous phase (comprising in particular hydrophilic filters) generally represents from 50 to 95% by weight, preferably from 70 at 90% by weight, relative to the whole of the formulation
- the oily phase (comprising in particular the lipophilic filters) from 5 to 50% by weight, preferably from 10 to 30% by weight, relative to the whole of the formulation
- the (co) emulsifier (s) from 0.5 to 20% by weight, preferably from 2 to 10% by weight, relative to the whole of the formulation.
- an object of the invention is the use of a composition as defined above for the manufacture of a cosmetic or dermatological composition intended for the protection of the skin and / or the hair against radiation ultraviolet, especially solar radiation.
- Another object of the present invention resides in a method for improving the stability of at least one dibenzoylmethane derivative with respect to UV radiation, consisting in associating with said dibenzoylmethane derivative an effective amount of at least one UV filter of the dimer type derived from ⁇ -alkylstyrene of formula (I) as defined above.
- Another object of the present invention consists in the use of a UV filter of the dimer type derived from ⁇ -alkylstyrene of formula (I) as defined above in the preparation of a cosmetic or dermatological composition comprising at least a UV filter of the type derived from dibenzoylmethane with the aim of improving the stability with respect to UV rays of said derivative of dibenzoylmethane.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002524464A JP2004526665A (ja) | 2000-09-05 | 2001-08-23 | ジベンゾイルメタン誘導体とα−アルキルスチレン二量体を含む組成物、UV安定化法 |
EP01963119A EP1367986A2 (fr) | 2000-09-05 | 2001-08-23 | COMPOSITION FILTRANTE CONTENANT UN DERIVE DU DIBENZOYLMETHANE ET UN DIMERE DERIVE D'$g(a)-ALKYLSTYRENE, PROCEDE DE PHOTOSTABILISATION |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR00/11304 | 2000-09-05 | ||
FR0011304A FR2813526A1 (fr) | 2000-09-05 | 2000-09-05 | Procede de photostabilisation de filtres solaires derives du dibenzoylmethane par un dimere derive d'alpha-alkylstyrene |
FR00/16791 | 2000-12-21 | ||
FR0016791A FR2813527B1 (fr) | 2000-09-05 | 2000-12-21 | Composition filtrante photostable contenant un derive du dibenzoylmethane et un dimere derive d'alpha-alkylstyrene, procede de photostabilisation |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002019979A2 true WO2002019979A2 (fr) | 2002-03-14 |
WO2002019979A3 WO2002019979A3 (fr) | 2002-08-15 |
Family
ID=26212600
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2001/002655 WO2002019979A2 (fr) | 2000-09-05 | 2001-08-23 | COMPOSITION FILTRANTE CONTENANT UN DERIVE DU DIBENZOYLMETHANE ET UN DIMERE DERIVE D'α-ALKYLSTYRENE, PROCEDE DE PHOTOSTABILISATION |
Country Status (5)
Country | Link |
---|---|
US (1) | US20030165443A1 (fr) |
EP (1) | EP1367986A2 (fr) |
JP (1) | JP2004526665A (fr) |
FR (1) | FR2813527B1 (fr) |
WO (1) | WO2002019979A2 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1449516A1 (fr) * | 2003-02-21 | 2004-08-25 | Beiersdorf AG | Emulsion cosmétique et dermatologique comprenant des esters d'acide phosphorique |
DE102010042147A1 (de) * | 2010-10-07 | 2012-04-12 | Beiersdorf Ag | Konservierungsmittelfreies Sonnenschutzmittel |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19855649A1 (de) * | 1998-12-03 | 2000-06-08 | Basf Ag | Dimere alpha-Alkyl-Styrolderivate als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2544180C2 (de) * | 1975-10-03 | 1984-02-23 | Merck Patent Gmbh, 6100 Darmstadt | Lichtschutzmittel für kosmetische Zwecke |
-
2000
- 2000-12-21 FR FR0016791A patent/FR2813527B1/fr not_active Expired - Fee Related
-
2001
- 2001-08-23 JP JP2002524464A patent/JP2004526665A/ja active Pending
- 2001-08-23 EP EP01963119A patent/EP1367986A2/fr not_active Withdrawn
- 2001-08-23 US US10/129,483 patent/US20030165443A1/en not_active Abandoned
- 2001-08-23 WO PCT/FR2001/002655 patent/WO2002019979A2/fr not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19855649A1 (de) * | 1998-12-03 | 2000-06-08 | Basf Ag | Dimere alpha-Alkyl-Styrolderivate als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1449516A1 (fr) * | 2003-02-21 | 2004-08-25 | Beiersdorf AG | Emulsion cosmétique et dermatologique comprenant des esters d'acide phosphorique |
DE102010042147A1 (de) * | 2010-10-07 | 2012-04-12 | Beiersdorf Ag | Konservierungsmittelfreies Sonnenschutzmittel |
Also Published As
Publication number | Publication date |
---|---|
FR2813527B1 (fr) | 2004-01-23 |
EP1367986A2 (fr) | 2003-12-10 |
FR2813527A1 (fr) | 2002-03-08 |
US20030165443A1 (en) | 2003-09-04 |
JP2004526665A (ja) | 2004-09-02 |
WO2002019979A3 (fr) | 2002-08-15 |
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