Photoprotective compositions comprising a dibenzoylmethane derivative, a merocyanine compound and a compound capable of accepting the triplet excited level energy of the dibenzoylmethane compound

Abstract

The present invention relates to a photoprotective composition for topical use comprising, in a cosmetically acceptable medium, at least one dibenzoylmethane derivative compound, at least one merocyanine compound and at least one compound capable of accepting the triplet excited level energy of said dibenzoylmethane derivative compound(s). The invention also relates to the use of at least one compound capable of accepting the triplet excited level energy of said dibenzoylmethane derivative compound(s), for photostabilizing with respect to UV radiation a composition comprising at least one dibenzoylmethane derivative compound and at least one merocyanine compound.

Claims

1. Photoprotective composition for topical use, characterized in that it comprises, in a cosmetically acceptable medium: (i) from 0.3% to 10% by weight of 4-tert-butyl-4′-methoxydibenzoylmethane, relative to the total weight of the composition; (ii) from 0.3% to 10% of 2-ethoxyethyl 2-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate, relative to the total weight of the composition; and (iii) from 0.001% to 10% by weight, relative to the total weight of the composition, of at least one compound capable of accepting the triplet excited level energy of 4-tert-butyl-4′-methoxydibenzoylmethane chosen from diethylhexyl syringylidenemalonate or tris(tetramethylhydroxypiperidinol) citrate.

2. Composition according to claim 1, characterized in that the total content of 4-tert-butyl-4′-methoxydibenzoylmethane (i) is between 0.3% and 5% by weight, relative to the total weight of the composition.

3. Composition according to claim 1, characterized in that the total content of 2-ethoxyethyl 2-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (ii) is between 0.3% and 5% by weight, relative to the total weight of the composition.

4. Composition according to claim 1, characterized in that the total content of the compound(s) (iii) capable of accepting the triplet excited level energy of 4-tert-butyl-4′-methoxydibenzoylmethane chosen from diethylhexyl syringylidenemalonate or tris(tetramethylhydroxypiperidinol) citrate is between 0.005% and 5% by weight, relative to the total weight of the composition.

5. Composition according to claim 1, characterized in that the ratio of the weight content of the compound(s) (iii) capable of accepting the triplet excited level energy of 4-tert-butyl-4′-methoxydibenzoylmethane chosen from diethylhexyl syringylidenemalonate or tris(tetramethylhydroxypiperidinol) citrate to the sum of the weight contents of 4 tert-butyl-4′-methoxydibenzoylmethane (i) and of 2 ethoxyethyl 2-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (ii), is between 0.01 and 20.

6. Composition according to claim 1, characterized in that it also comprises one or more additional UV-screening agents chosen, alone or as a mixture, from anthranilates; salicylic derivatives; benzylidenecamphor derivatives; benzophenone derivatives; β,β-diphenylacrylate compounds different from ethylhexyl methoxycrylene derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imidazolines; bisbenzoazolyl derivatives; p-aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenyl benzotriazole) derivatives; benzoxazole derivatives; screening polymers and screening silicones; α-alkylstyrene-based dimers; 4,4-diarylbutadienes; and/or treated or untreated metal oxide pigments or nanopigments, and mixtures thereof.

7. Composition according to claim 6, in which the additional UV-screening agents are chosen, alone or as a mixture, from the following UV-screening agents: ethylhexyl salicylate, octocrylene, phenylbenzimidazole sulfonic acid, benzophenone-3, benzophenone-4, benzophenone-5, n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate, 4-methylbenzylidenecamphor, terephthalylidenedicamphorsulfonic acid, disodium phenyldibenzimidazole tetrasulfonate, methylenebisbenzotriazolyl tetramethylbutylphenol, ethylhexyl triazone, diethylhexyl butamido triazone, drometrizole trisiloxane, polysilicone-15, 1,1-dicarboxy(2,2′-dimethylpropyl)-4,4-diphenylbutadiene, 2,4-bis[5-1-(dimethylpropyl)benzoxazol-2-yl(4-phenyl)imino]-6-(2-ethylhexyl)imino-1,3,5-triazine, and mixtures thereof.

8. Composition according to claim 1, characterized in that it comprises at least one oil chosen from hydrocarbon-based oils, silicone oils, fluoro oils, and/or mixtures thereof.

9. Composition according to claim 1, characterized in that it is in the form of an oil-in-water or water-in-oil emulsion.

10. Cosmetic method for treating the skin against UV radiation, comprising at least one step of applying to the skin a composition as defined in claim 1.

11. A method of photostabilizing a composition comprising 4-tert-butyl-4′-methoxydibenzoylmethane and 2-ethoxyethyl 2-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate, with respect to UV radiation, (ii) the method comprising adding to the composition at least one compound capable of accepting the triplet excited level energy of 4-tert-butyl-4′-methoxydibenzoylmethane chosen from diethylhexyl syringylidenemalonate or tris(tetramethylhydroxypiperidinol) citrate, wherein the total content of 4-tert-butyl-4′-methoxydibenzoylmethane is between 0.3% and 10% by weight, relative to the total weight of the composition, wherein the total content of 2-ethoxyethyl 2-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate is between 0.3% and 10% by weight, relative to the total weight of the composition and wherein the total content of diethylhexyl syringylidenemalonate or tris(tetramethylhydroxypiperidinol) citrate is between 0.001% and 10% by weight, relative to the total content of the composition.

Description

EXAMPLES

(1) The compositions 1, 2 and 3 are prepared from the ingredients shown in the table below, the amounts of which are expressed as weight percentages of active material (AM).

(2) TABLE-US-00001 Composition Composition Composition 1 2 3 Phases Ingredients (Comparative) (Invention) (Invention) A Water qs qs qs Glycerol 5 5 5 Triethanolamine 0.45 0.45 0.45 Disodium EDTA 0.1 0.1 0.1 Preservative qs qs qs Ammonium acryloyldimethyltaurate/ 0.5 0.5 0.5 Steareth-8 MethacrylatE Copolymer (ARISTOFLEX SNC ®) B Isopropyl Lauroyl Sarcosinate 30 30 30 4-tert-butyl-4′-methoxydibenzoylmethane 2 2 2 2-ethoxyethyl 2-cyano{3-[(3- 1 1 1 methoxypropyl)amino]cyclohex-2-en-1- ylidene}ethanoate Diethylhexyl syringylidenemalonate + — 2 — 90/10 Caprylic/Capric Triglyceride (OXYNEX ST LIQUID) Tris(Tetramethylhydroxypiperidinol) — — 0.01 Citrate (TINOGARD QS) Stearyl Alcohol 1 1 1 Glyceryl Isostearate 0.5 0.5 0.5 C Isohexadecane 1 1 1 Xanthan gum 0.2 0.2 0.2 Ammonium Polyacryloyldimethyl 0.4 0.4 0.4 Taurate (HOSTACERIN AMPS ®)

(3) Composition Preparation Method:

(4) The aqueous phase A and the oily phase B were prepared by mixing the starting materials with mechanical stirring at 80° C. Once the aqueous phase A and the oily phase B are macroscopically homogeneous, the emulsion is prepared by introducing the phase B into the phase A with stirring by means of a rotor-stator homogenizer at a stirring speed of 4500 revolutions per minute for 20 minutes. The phase C is then added, and the composition is called to ambient temperature (25° C.).

(5) Results:

(6) Once the compositions 1 to 3 have been prepared, these are then irradiated under a UV-A sun lamp at 21.6 J/cm.sup.2, for one hour.

(7) After irradiation, the residual contents of the compounds 4-tert-butyl-4′-methoxydibenzoylmethane and 2-ethoxyethyl 2-cyano {3-[(3-methoxypropyl)amino]-cyclohex-2-en-1-ylidene}ethanoate in each of the compositions were measured by conventional HPLC chromatography methods.

(8) The residual content of the ingredient corresponds to the weight ratio of the content of the ingredient after UV irradiation to the content of the ingredient before UV irradiation. The residual contents are expressed as percentages.

(9) The results obtained are collated in the table below:

(10) TABLE-US-00002 Residual contents Composition 1 Composition 2 Composition 3 after irradiation (Comparative) (Invention) (Invention) 4-tert-butyl-4′-methoxydibenzoylmethane 72% 86% 87% 2-ethoxyethyl 2-cyano{3-[(3- 46% 72% 71% methoxypropyl)amino]cyclohex- 2-en-1-ylidene}ethanoate

(11) These results show that the compositions 2 and 3 according to the invention exhibit residual contents of the dibenzoylmethane derivative and of the merocyanine compound that are substantially higher compared with the comparative composition 1, and thus exhibit better photostability with respect to UV radiation.