Patent FR-2967900-A1 (FR)
Title: Composition for protecting from sun or make up of skin, lips or hair comprises UV screening system comprising dibenzoylmethane derivative; and specific hydrophilic or water-soluble merocyanine UV-screening agent
Inventor: RICHARD HERVE
IPC: A61K8/35
Filed: 2010-11-25
Abstract: A composition comprises: in cosmetic vehicle, UV screening system(s) comprising dibenzoylmethane derivative(s); and hydrophilic or water-soluble merocyanine UV-screening agent(s) selected from ((E)-buta-1,3-dienyl)-disubstituted-amine compounds, cyclobut-1-enylamine compounds, and merocyanine compounds selected from 36 compounds as given in the specification e.g. sodium 4-{2-[(Z)-3-cyano-3-methanesulfonyl-prop-2-en-(E)-ylidene]-thiazolidin-3-yl}-butane-1-sulfonate, and their salts or E,E-, E,Z-, or Z,Z- isomers. A composition comprises: in a cosmetic vehicle, at least one UV screening system comprising at least one dibenzoylmethane derivative; and at least one hydrophilic or water-soluble merocyanine UV-screening agent selected from ((E)-buta-1,3-dienyl)-disubstituted-amine compound of formula [NR 1R 2-CH=CH-CH=CR 3R 4] n(I), and cyclobut-1-enylamine compound of formula (II), and their salts or E,E-, E,Z-, or Z,Z- geometrical isomer forms, and merocyanine compounds (III) selected from 36 compounds as given in the specification e.g. sodium 4-{2-[(Z)-3-cyano-3-methanesulfonyl-prop-2-en-(E)-ylidene]-thiazolidin-3-yl}-butane-1-sulfonate; (Z)-2-cyano-4-[3-methyl-oxazolidin-(2E)-ylidene]-but-2-enoic acid 2-sulfo-ethyl ester; 2-{2-[(Z)-3-cyano-3-(octane-1-sulfonyl)-prop-2-en-(E)-ylidene]-oxazolidin-3-yl}-ethanesulfonic acid; (2E,4E)-5-(4-hydroxy-piperidin-1-yl)-2-methanesulfonyl-penta-2,4-dienoic acid methyl ester; 2-[(E)-3-(4-hydroxy-piperidin-1-yl)-allylidene]-malonic acid diethyl ester; (2E,4E)-2-cyano-5-(4-hydroxy-piperidin-1-yl)-penta-2,4-dienoic acid octyl ester; (2Z,4E)-5-[bis-(2-hydroxy-ethyl)-amino]-2-cyano-penta-2,4-dienoic acid pentyl ester; (2E,4E)-2-cyano-5-[ethyl-(2-hydroxy-ethyl)-amino]-penta-2,4-dienoic acid octyl ester; (2Z,4E)-5-[bis-(2-hydroxy-ethyl)-amino]-2-cyano-penta-2,4-dienoic acid isopropyl ester; (2E,4E)-2-cyano-5-[ethyl-(2-hydroxy-ethyl)-amino]-penta-2,4-dienoic acid 1-methyl-heptyl ester; (2Z,4E)-5-[bis-(2-hydroxy-ethyl)-amino]-2-cyano-penta-2,4-dienoic acid 1-methyl-heptyl ester; (2E,4E)-2-cyano-5-(2-hydroxy-ethylamino)-penta-2,4-dienoic acid octyl ester; (2E,4E)-2-cyano-5-(1-hydroxymethyl-2-methyl-propylamino)-penta-2,4-dienoic acid heptyl ester; (2E,4E)-2-cyano-5-dimethylamino-penta-2,4-dienoic acid (2,3-dihydroxy-propyl)-amide; (2E,4E)-2-cyano-5-[ethyl-(2-hydroxy-ethyl)-amino]-penta-2,4-dienoic acid 3-{(2E,4E)-2-cyano-5-[ethyl-(2-hydroxy-ethyl)-amino]-penta-2,4-dienoyloxy}-propyl ester, and their salts or E,E-, E,Z-, or Z,Z- geometrical isomer forms. R 1, R 2, R' 1and R' 2 : linear or branched 1-22C alkyl (optionally containing 1-3 O atoms) or 3-8C cycloalkyl (optionally substituted with 1-4C alkyl) (both optionally containing alkylsulfonate in its acid or salified form, or 1 or 2 hydroxyl), alkyl diradical, or H;or NR 1R 2or NR' 1R' 2 : ring containing a group -(CH 2) m- (optionally interrupted with at least one -O-, -S- or -NH-);or R 1or R' 1+carbon alpha to nitrogen : ring containing a group -(CH 2) m- (optionally interrupted with at least one -O-, -S- or -NH-); R 3and R' 3 : carboxyl, -COOR 5, -CONHR 5, -COR 5, -CONR 5R 1, SO 2R 5, or CN; R 4and R' 4 : carboxyl, -COOR 6, -CONHR 6, -COR 6, -CONR 6R 2, or SO 2R 6; R 5and R 6 : linear or branched 1-22C alkyl (optionally containing 1-3 O atoms) or 3-8C cycloalkyl (optionally substituted with 1-4C alkyl) (both optionally containing alkylsulfonate in its acid or salified form, or 1 or 2 hydroxyl), or alkyl diradical; Z' : group of formula -(CH 2) l- (optionally interrupted with -O-, -S- or -NR 7-, and optionally substituted with 1 or 2 1-6C alkyl); R 7 : 1-5C alkyl (optionally containing alkylsulfonate in its acid or salified form, or 1 or 2 hydroxyl); n : 1 or 2; m : 1-7; l : 1-4. Provided that: (1) at least 1 or 2 of the R 1or R' 1, R 2or R' 2, R 5, R 6and R 7contains either an alkylsulfonate in its acid or salified form; or 1 or 2 hydroxyl; (2) when n is 2, one of R 1or R' 1, R 5or R 6is alkyl diradical; or NR 1R 2or NR' 1R' 2forms cyclic divalent -(CH 2) m- radical; (3) R 1and R 2or R' 1and R' 2are not simultaneously H; and (4) when R 3or R' 3is CN, then at least one of R 1or R' 1, R 2or R' 2, and R 6contains alkylsulfonate in its acid or salified form. Independent claims are included for the following: (1) method (M1) for improving the chemical stability towards UV radiation of a least one dibenzoylmethane derivative, involving: combining the dibenzoylmethane derivative with at least one hydrophilic or water-soluble merocyanine UV screening agent selected from compounds (I), (II) and (III), or their salt or E,E-, E,Z-, or Z,Z- isomeric form; (2) new merocyanine compounds (I) containing one or two alkylsulfonate radicals or containing hydroxyl groups including 27 compounds as given in the specification e.g. ((2E,4E)-2-cyano-5-dimethylamino-penta-2,4-dienoylamino)-methanesulfonic acid; ((2E,4E)-2-cyano-5-diethylamino-penta-2,4-dienoylamino)-methanesulfonic acid; 2-((E)-3-dimethylamino-allylidene)-malonic acid bis-(2-sulfo-ethyl) ester; (2E,4E)-5-[bis-(2-hydroxy-ethyl)-amino]-2-methanesulfonyl-penta-2,4-dienoic acid methyl ester; and 2-((E)-3-dimethylamino-allylidene)-malonic acid bis-(4-hydroxy-butyl) ester; and their salt or E-E, Z-Z, ad E-Z isomer forms; (3) new merocyanine compounds (II) including 2-(3-sec-butylamino-5,5-dimethyl-cyclohex-2-enylidene)-malonic acid bis-(4-hydroxy-butyl) ester; [3-[bis-(2-hydroxy-ethyl)-amino]-5,5-dimethyl-cyclohex-2-en-(E)-ylidene]-methanesulfonyl-acetic acid octyl ester, and their salt or E-E, Z-Z, and E-Z isomer forms; and (4) new merocyanine compounds (III), and their salts or E-E, E-Z or Z-Z isomeric forms. 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