WO2007080052A1 - Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé de phénol ou de bisphénol contenant du siloxane, et procédé de photostabilisation du dérivé de dibenzoylméthane - Google Patents

Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé de phénol ou de bisphénol contenant du siloxane, et procédé de photostabilisation du dérivé de dibenzoylméthane Download PDF

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Publication number
WO2007080052A1
WO2007080052A1 PCT/EP2006/070078 EP2006070078W WO2007080052A1 WO 2007080052 A1 WO2007080052 A1 WO 2007080052A1 EP 2006070078 W EP2006070078 W EP 2006070078W WO 2007080052 A1 WO2007080052 A1 WO 2007080052A1
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derivatives
composition according
formula
radical
chosen
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PCT/EP2006/070078
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English (en)
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Hervé Richard
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L'oréal
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    • 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
    • A61K8/72—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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Definitions

  • the present invention relates to a cosmetic composition containing the combination of a dibenzoylmethane derivative and a specific siloxane-containing phenol or bisphenol compound of formula (I) or (II), the definitions of which will be given hereinafter.
  • It also relates to a process for the photo- stabilization, against radiation, of at least one dibenzoylmethane derivative with at least one specific siloxane-containing phenol or bisphenol compound of formula (I) or (II) .
  • the present invention also relates to the use of said siloxane-containing phenol or bisphenol compound in a composition comprising, in a cosmetically acceptable support, at least one UV-A-screening agent of the dibenzoylmethane derivative type with the aim of improving the effectiveness of said composition against UV-A rays .
  • UV-B Light radiation with wavelengths in the range 280 nm to 400 nm is known to brown the human epidermis; more particularly, rays with a wavelength in the range 280 to 320 nm, known as UV-B, are known to cause erythema and skin burns that may be deleterious to the development of a natural tan. For these reasons and for aesthetic reasons, there exists a constant demand for means for controlling this natural tanning which can thereby control the colour of the skin; it is therefore advisable to screen out said UV-B radiation.
  • UV-A rays with wavelengths in the range 320 to 400 nm which cause the skin to brown, are capable of inducing alterations in said skin, in particular in the case of sensitive skin or of skin continually exposed to solar radiation.
  • UV-A rays in particular cause a loss of elasticity of the skin and the appearance of wrinkles, resulting in premature ageing of the skin. They promote triggering of the erythematous reaction or amplify this reaction in certain individuals and may even be the cause of phototoxic or photo-allergic reactions.
  • sunscreen compositions comprising organic screening agents, which are active in the UV-A range and active in the UV-B range, are generally used.
  • organic screening agents which are active in the UV-A range and active in the UV-B range.
  • the majority of these screening agents are liposoluble.
  • UV-A screening agents currently consists of dibenzoyl- methane derivatives, and in particular 4-tert-butyl- 4 ' -methoxydibenzoylmethane, which in fact have an extremely good intrinsic absorbing capacity.
  • dibenzoylmethane derivatives are relatively sensitive to ultraviolet radiation (especially UV-A), i.e., more specifically, they have an annoying tendency to degrade more or less rapidly under the action of said radiation.
  • UV-A ultraviolet radiation
  • this substantial lack of photochemical stability of dibenzoylmethane derivatives in the face of the ultraviolet radiation to which they are, by nature, intended to be subjected cannot guarantee constant protection during prolonged exposure to the sun, and means that repeated applications at regular, close intervals have to be made by the user in order to effectively protect the skin against UV rays.
  • composition comprising, in a cosmetically acceptable support, at least one UV-screening system, characterized in that it comprises:
  • Another subject of the invention also concerns a process for improving the chemical stability, against UV radiation, of at least one UV-A-screening agent of the dibenzoylmethane derivative type, consisting in combining with said dibenzoylmethane derivative at least one specific siloxane-containing phenol or bisphenol compound of formula (I) or (II) , the definitions of which will be given hereinafter.
  • a subject of the present invention is also the use of a specific siloxane-containing phenol or bisphenol compound of formula (I) or (II) , in a composition comprising, in a cosmetically acceptable support, at least one dibenzoylmethane derivative with the aim of improving the effectiveness of said composition against UV-A rays.
  • cosmetically acceptable is intended to mean compatible with the skin and/or its integuments, which has a pleasant colour, odour and feel and which does not generate any unacceptable discomfort (stinging, tautness, red blotches), liable to discourage consumers from using this composition.
  • dibenzoylmethane derivatives mention may in particular be made, in a non-limiting manner, of:
  • the dibenzoylmethane derivative (s) may be present in the compositions in accordance with the invention at contents that preferably range from 0.01% to 20% by weight, and more preferably from 0.1% to 10% by weight, and even more preferably from 0.1% to 6% by weight, relative to the total weight of the composition.
  • R 1 which may be identical or different, denote hydrogen or a Ci-C 4 alkyl radical, or else two adjacent radicals Ri can together form a C 5 -C 7 ring, R 2 denotes:
  • Ci-C 20 alkyl radical that may contain at least one substituent chosen from a C 5 -C 7 carbon-based ring and an oxygen, nitrogen, sulphur or silicon atom;
  • R 3 which may be identical or different, represent - a Ci-C 20 alkoxy radical that may be substituted with at least one oxygen or silicon,-
  • Ci-C 20 alkyl or hydroxyalkyl that may contain at least one substituent chosen from a C 5 -C 7 carbon-based ring and an oxygen, nitrogen, sulphur or silicon atom;
  • tert-alkyl radical for example, tert-butyl
  • B is a divalent radical chosen from the group corres- ponding to one of the following formulae (III) , (IV) and (V) : CH 2 -CH-(Z) V - (in)
  • Z is a saturated or unsaturated, linear or branched C 1 -C 6 alkylene radical optionally substituted with a hydroxyl radical or a saturated or unsaturated, linear or branched C 1 -C 8 alkyl radical,
  • W represents a hydrogen atom, a hydroxyl radical or a saturated or unsaturated, linear or branched C 1 -C 8 alkyl radical, v is 0 or 1 , q is 0 or 1 .
  • the organosiloxane may contain units of formula (R) b- (Si) (0) (4-b)/2 in which:
  • the groups -(Si) (R) a (0) (3-a)/ 2 can be represented by the following formula (VI) or (VII) :
  • (E) is a link between the silicone chain and the group B of the phenols of formula (I) or (II) ,
  • R 4 which may be identical or different, are chosen from linear or branched Ci-C 2 O alkyl radicals, phenyl, 3 , 3 , 3-trifluoropropyl and trimethylsilyloxy, at least 80% by number of the radicals R 4 being methyl
  • (D) which may be identical or different, are chosen from the radicals R 4 and the radical (E)
  • r is an integer between 0 and 200 inclusive
  • s is an integer between 0 and 50 inclusive
  • u is an integer between 1 and 10 inclusive
  • t is an integer between 0 and 10 inclusive, it being understood that t + u is greater than or equal to 3, with the proviso that, when q is 1, then u is equal to 1, s is equal to 1 and the symbol (D) cannot denote B or s is equal to 0 and only one of the symbols (D) denotes B .
  • linear or cyclic diorganosiloxanes of formula (VI) or (VII) falling within the scope of the present invention are random oligomers or polymers that preferably have at least one, and even more preferably all, of the following characteristics:
  • R 4 is preferably methyl
  • - (D) is preferably methyl (in the case of the linear compounds of formula (VI) ) .
  • the compounds of formula (I) can be obtained conventionally by carrying out a hydrosilylation reaction using a siloxane derivative of formula (VIII) , in which, for example, all the (E) s are hydrogen atoms (this derivative is subsequently referred to as SiH-containing derivative) , and an unsaturated derivative of formula (IX) or (X) , according to the following reaction scheme:
  • the SiH groups can be present in the chain or at the ends of the chain.
  • These SiH-containing derivatives are products that are well known in the silicone industry and are in general commercially available. They are, for example, described in American patents US 3220972, US 3697473 and US 4340709.
  • the compounds of formulae (I) and (II) in accordance with the invention are preferably present in the compositions in accordance with the invention at contents of from 0.01% to 20% by weight, and more preferably from 0.1% to 10%, and even more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • the compound (s) of formulae (I) and (II) will be used in an amount sufficient to obtain a notable and significant improvement in the photostability of the dibenzoylmethane derivative in a given composition.
  • This minimal amount of photostabilizing agent to be used may vary according to the amount of dibenzoylmethane present at the start in the composition and according to the nature of the cosmetically acceptable support selected for the composition. It may be determined without any difficulty by means of a conventional test for measuring photostability.
  • compositions in accordance with the invention may also contain other additional organic or inorganic UV--screening agents active in the UV-A range and/or in the UV-B range, that are water-soluble or liposoluble or else insoluble in the cosmetic solvents commonly used .
  • the additional organic photoprotective agents are in particular chosen from anthranilates,- cinnamic derivatives; salicylic derivatives, camphor derivatives; benzophenone derivatives; ⁇ , ⁇ -diphenyl acrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives, in particular those mentioned in patent US 5624663; benzimidazole derivatives; imidazolines; bisbenzoazolyl derivatives, as described in patents EP669323 and US 2,463,264; p-aminobenzoic acid (PABA) derivatives; methylenebis (hydroxyphenylbenzotriazole) derivatives as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; benzoxazole derivatives as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; screening polymers and screening silicones such as those described in particular in application
  • Ethyl dihydroxypropyl PABA Ethylhexyl dimethyl PABA, sold in particular under the name "ESCALOL 507" by ISP,
  • Ethylhexyl methoxycinnamate sold in particular under the trade name "PARSOL MCX” by Hoffmann La Roche,
  • 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,
  • Benzophenone-3 or oxybenzone sold under the trade name "UVINUL M40" by BASF
  • Benzophenone-4 sold under the trade name "UVINUL MS40” by BASF
  • Benzophenone-5 sold under the trade name "UVINUL M40" by BASF
  • Benzophenone-6 sold under the trade name "Helisorb 11" by Norquay
  • Benzophenone- 8 sold under the trade name "Spectra-Sorb UV-24” by American Cyanamid
  • Benzophenone- 9 sold under the trade name "UVINUL DS-49" by BASF, Benzophenone- 12, n-Hexyl 2- (4-diethylamino-2 ⁇ hydroxybenzoyl)benzoate
  • Phenylbenzimidazole sulphonic acid sold in particular under the trade name "EUSOLEX 232" by MERCK, Disodium phenyl dibenzimidazole tetrasulphonate sold under the trade name "NEO HELIOPAN AP” by HAARMANN and REIMER,
  • Phenylbenzotriazole derivatives Drometrizole trisiloxane sold under the name "Silatrizole” by RHODIA CHIMIE,
  • Ethylhexyl triazone sold in particular under the trade name "UVINUL T150" by BASF,
  • UVASORB HEB Diethylhexyl butamido triazone sold under the trade name "UVASORB HEB” by SIGMA 3V, 2,4, 6-tris (Dineopentyl 4 ' -aminobenzalmalonate) -s- triazine,
  • HELIOPAN MA by HAARMANN and REIMER
  • Benzalmalonate derivatives Dineopentyl 4 ' -methoxybenzalmalonate
  • Polyorganosiloxane comprising benzalmalonate functions such as polysilicone-15 sold under the trade name "PARSOL SLX” by Hoffmann La Roche,
  • Benzoxazole derivatives 2 , 4-bis [5-1- (Dimethylpropyl) benzoxazol-2-yl-
  • the preferred additional organic photoprotective agents are chosen from:
  • Ethylhexyl triazone bis (Ethylhexyloxyphenol methoxyphenyl triazine) ,
  • the inorganic photoprotective agents are chosen from pigments or else nanopigments (mean size of the primary particles: generally between 5 nm and 100 ran, preferably between 10 nm and 50 nm) of coated or uncoated metal oxides such as, for example, nanopigments of titanium oxide (amorphous or crystalline in rutile and/or anatase form), iron oxide, zinc oxide, zirconium oxide or cerium oxide, and mixtures thereof.
  • Conventional coating agents are, moreover, alumina and/or aluminium stearate .
  • Such coated or uncoated metal oxide nanopigments are in particular described in patent applications EP 518 772 and EP 518 773.
  • the additional photoprotective agents are generally present in the compositions according to the invention in proportions ranging from 0.01% to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.1% to 10% by weight relative to the total weight of the composition.
  • the nanopigments treated are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, pp. 53-64, such as aminoacids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium salts, potassium salts, zinc salts, iron salts or aluminium salts of fatty acids, metal (titanium or aluminium) alkoxides, polyethylene, silicones, proteins (collagen, elastin) , alkanolamines, silicon oxides, metal oxides, sodium hexametaphosphate, alumina or glycerol.
  • surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, pp. 53-64 such as aminoacids, beeswax,
  • the treated nanopigments may more particularly be titanium oxides treated with: - silica and alumina, such as the products “Microtitanium Dioxide MT 500 SA” and “Microtitanium Dioxide MT 100 SA” from the company TAYCA, and the products “Tioveil Fin”, “Tioveil OP”, “Tioveil MOTG” and “Tioveil IPM” from the company TIOXIDE, - alumina and aluminium stearate, such as the product
  • UVT- M160 alumina and stearic acid
  • UVT-M212 alumina and glycerol
  • titanium oxide nanopigments treated with a silicone are preferably TiO 2 treated with octyltrimethylsilane, the mean size of the elemental particles of which is between 25 and 40 nm, such as the product sold under the trade name "T 805" by the company DEGUSSA SILICES, TiO 2 treated with a polydimethylsiloxane, the mean size of the elemental particles of which is 21 nm, such as the product sold under the trade name "70250 Cardre UF T1O2SI3" by the company CARDRE, anatase/rutile TiO 2 treated with a polydimethylhydrogenosiloxane, the mean size of the elemental particles of which is 25 nm, such as the product sold under the trade name "Micro Titanium Dioxide USP Grade Hydrophobic" by the company COLOR TECHNIQUES.
  • the uncoated titanium oxide nanopigments are, for example, sold by the company TAYCA under the trade names "Microtitanium Dioxide MT 500 B” or “Microtitanium Dioxide MT600 B", by the company DEGUSSA under the name "P 25”, by the company WACKHER under the name “Oxyde de titane transparent PW”, by the company MIYOSHI KASEI under the name "UFTR” , by the company TOMEN under the name "ITS” and by the company TIOXIDE under the name "TIOVEIL AQ”.
  • the uncoated zinc oxide nanopigments are, for example:
  • Nanophase Technologies those sold under the name “Nanogard WCD 2025” by the company Nanophase Technologies .
  • coated zinc oxide nanopigments are, for example:
  • the uncoated cerium oxide nanopigments are sold under the name "COLLOIDAL CERIUM OXIDE” by the company RHONE POULENC .
  • the uncoated iron oxide nanopigments are, for example, sold by the company ARNAUD under the names "NANOGARD WCD 2002 (FE 45B)", “NANOGARD IRON FE 45 BL AQ”, “NANOGARD FE 45R AQ” or “NANOGARD WCD 2006 (FE 45R)", or by the company MITSUBISHI under the name "TY-220" .
  • coated iron oxide nanopigments are, for example, sold by the company ARNAUD under the names "NANOGARD WCD 2008 (FE 45B FN)", “NANOGARD WCD 2009 (FE 45B 556)", “NANOGARD FE 45 BL 345" and “NANOGARD FE 45 BL”, or by the company BASF under the name "OXYDE DE FER TRANSPARENT” .
  • the nanopigments can be introduced into the compositions according to the invention as they are or in the form of a pigmentary paste, i.e. as a mixture with a dispersing agent, as described, for example, in document GB-A-2206339.
  • the additional photoprotective agents are generally present in the compositions according to the invention in proportions ranging from 0.01% to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.1% to 10% by weight relative to the total weight of the composition.
  • compositions according to the invention can also contain artificial tanning and/or browning agents for the skin (self-tanning agents) , and more particularly dihydroxyacetone (DHA) . They are preferably present in amounts ranging from 0.1% to 10% by weight relative to the total weight of the composition.
  • artificial tanning and/or browning agents for the skin self-tanning agents
  • DHA dihydroxyacetone
  • compositions in accordance with the present invention can also comprise conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, hydrophilic or lipophilic, ionic or non- ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, anti- foams, fragrances, preserving agents, anionic, cationic, non- ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, basifying or acidifying agents, or any other ingredient normally used in the cosmetics and/or dermatological field.
  • conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, hydrophilic or lipophilic, ionic or non- ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, anti- foams, fragrances, preserving agents, anionic, cationic, non- ionic
  • the fatty substances may consist of an oil or a wax or mixtures thereof.
  • oil is intended to mean a compound that is liquid at ambient temperature.
  • wax is intended to mean a compound that is solid or substantially solid at ambient temperature, and the melting point of which is generally above 35°C.
  • oils mention may be made of mineral oils (paraffin); plant oils (sweet almond oil, macadamia oil, blackcurrant seed oil, jojoba oil); synthetic oils such as perhydrosqualene, fatty alcohols, acids or esters (such as the Ci 2 -Ci 5 alkyl benzoate sold under the trade name "Finsolv TN" by the company WITCO, octyl palmitate, isopropyl lanolate, triglycerides, including those of capric/caprylic acids) , oxyethylenated or oxypropylenated fatty esters and ethers; silicone oils
  • cyclomethicone polydimethylsiloxanes or PDMSs
  • fluoro oils polyakylenes
  • waxy compounds mention may be made of paraffin, carnauba wax, beeswax and hydrogenated castor oil.
  • organic solvents mention may be made of lower alcohols and polyols. The latter may be chosen from glycols and glycol ethers, such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol .
  • carboxyvinyl polymers such as carbopols (carbomers) and pemulens (acrylate/Ci O -C 3O alkyl acrylate copolymer)
  • polyacrylamides such as, for example, the crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide/C 13 -i4 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyltaurate copolymer/isohexadecane/ polysorbate 80) by the company Seppic
  • modified clays such as hectorite and its derivatives, for instance the products sold under the name Bentone .
  • - NO-synthase inhibitors - agents for stimulating the synthesis of dermal or epidermal macromolecules and/or preventing their degradation
  • compositions according to the invention can be prepared according to the techniques well known to those skilled in the art, in particular those intended for the preparation of emulsions of oil-in-water or water-in-oil type. They can in particular be in the form of a simple or complex (O/W, W/O, 0/W/O or W/O/W) emulsion such as a cream or a milk, or in the form of a gel or of a cream-gel, in the form of a lotion, a powder or a solid stick, and can optionally be packaged as an aerosol and be in the form of a foam or a spray.
  • a simple or complex (O/W, W/O, 0/W/O or W/O/W) emulsion such as a cream or a milk, or in the form of a gel or of a cream-gel, in the form of a lotion, a powder or a solid stick, and can optionally be packaged as an aerosol and be in the form of a foam or
  • compositions according to the invention are in the form of an oil-in-water or water-in-oil emulsion.
  • the emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or non-ionic emulsifiers, used alone or as a mixture.
  • the emulsifiers are chosen appropriately depending on the emulsion to be obtained (W/0 or 0/W) .
  • emulsifying surfactants that can be used for the preparation of the W/0 emulsions, mention may, for example, be made of alkyl esters or ethers of sorbitan, of glycerol or of sugars; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, sold under the name "DC 5225 C" by the company Dow Corning, and alkyl dimethicone copolyols such as the laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid” by the company Dow Corning; cetyl dimethicone copolyol such as the product sold under the name Abil EM 9OR by the company Goldschmidt and the mixture of cetyl dimethicone copolyol, of polyglyceryl isostearate (4 mol of glycerol) and of hexyl laur
  • co-emulsifiers can also be added thereto, which co-emulsifiers can, advantageously, be chosen from the group comprising polyol alkyl esters.
  • polyol alkyl esters mention may in particular be made of esters of glycerol and/or of sorbitan and, for example, polyglyceryl isostearate, such as the product sold under the name Isolan GI 34 by the company Goldschmidt, sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI, and the mixture of sorbitan isostearate and of glycerol, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof .
  • emulsifiers that may, for example, be mentioned include non- ionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers,- sugar esters such as sucrose stearate,- ethers of a fatty alcohol and of a sugar, in particular alkylpolyglucosides (APGs) such as the decylglucoside and the laurylglucoside sold, for example, by the company Henkel under the respective names Plantaren 2000 and Plantaren 1200, the cetostearylglucoside optionally as
  • APGs alkylpolyglu
  • the mixture of alkylpolyglucoside as defined above with the corresponding fatty alcohol can be in the form of a self-emulsifying composition, as described, for example, in document WO-A-92/06778.
  • the aqueous phase of the latter may comprise a non-ionic vesicular dispersion prepared according to known processes (Bangham, Standish and Watkins, J. MoI. Biol. 13, 238 (1965), FR 2 315 991 and FR 2 416 008) .
  • compositions according to the invention find their application in a large number of treatments, in particular cosmetic treatments, for the skin, the lips and the hair, including the scalp, in particular for protecting and/or caring for the skin, the lips and/or the hair, and/or for making up the skin and/or the lips .
  • compositions according to the invention as defined above, for the manufacture of products for the cosmetic treatment of the skin, the lips, the nails, the hair, the eyelashes, the eyebrows and/or the scalp, in particular care products and makeup products.
  • compositions according to the invention may be used, for example, as a care product and/or an sunscreen product for the face and/or the body, of liquid to semi-liquid consistency, such as milks, more or less rich creams, cream-gels or pastes. They may optionally be packaged as an aerosol and may be in the form of a foam or a spray.
  • compositions according to the invention in the form of vapourizable fluid lotions in accordance with the invention are applied to the skin or the hair in the form of fine particles by means of pressurization devices.
  • the devices in accordance with the invention are well known to those skilled in the art and include non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and also aerosol pumps that use compressed air as propellant.
  • the latter pumps are described in patents US 4,077,441 and US 4,850,517 (forming an integral part of the content of the description) .
  • compositions packaged as an aerosol in accordance with the invention generally contain conventional propellants such as, for example, hydrofluoro compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane . They are preferably present in amounts ranging from 15% to 50% by weight relative to the total weight of the composition.
  • EXAMPLE A Preparation of 2-methoxy-4- (3- ⁇ 1,3,3,3-tetramethyl-l- [ (trimethylsilyl) oxy] di- siloxanyl ⁇ propyl) phenol ; compound (g) ;
  • the oil obtained is chromatographed on silica (eluent: 95:5 heptane/EtOAc) , to give 4.35 g (yield: 42%) of a pale yellow oil of the compound of Example 4. This oil crystallizes after one day (m.p. 60-1 0 C) .
  • the percentage loss of dibenzoylmethane derivative, induced by exposure to a solar simulator, of a formula spread into films in the region of 20 ⁇ m thick, is measured.
  • the evaluation is carried out by HPLC analysis of the screening agent in solution, after extraction of the films, by comparing irradiated and non-irradiated samples .
  • Solar simulator Oriel IOOOW device equipped with a 4-inch output, with an 81017 filter and a dichroic mirror. The samples are exposed in the horizontal position.
  • UV-meter OSRAM CENTRA device equipped with 2 reading heads, one for UVA and the other for UVB.
  • the simulator UV-meter assembly is calibrated annually by spectroradiometry.
  • Irradiance measurements carried out at the beginning and the end of exposure by placing the reading heads in the position of the sample.
  • the irradiances are:
  • the residual butyl methoxy dibenzoylmethane is measured by chromatography: HPLC system with diode array detector.
  • the phenols are introduced into the common support defined above at a content of 4% in the presence of 1% of butyl methoxy dibenzoylmethane of the composition.
  • the samples are exposed 3 at a time to the light of the solar simulator for a period of time sufficient to deliver a UVA dose equal to 12 G corrected with respect to the sensitivity of the UV-meter corresponding to the degradation of approximately 50% of the butyl methoxy dibenzoylmethane (Parsol 1789) in the absence of phenolic agent.
  • each support disc is introduced into a 600 ml container with 10 ml of an appropriate solvent (in general, EtOH); the whole is placed in an ultrasound tank for 5 minutes. The solution is then transferred into bottles suitable for the support compatible with the HPLC analytical device used.
  • an appropriate solvent in general, EtOH
  • the analytical conditions can be adjusted according to the active agent tested.
  • the phenolic compounds of formula (I) or (II) of Examples 1 to 4 according to the invention have a significant photostabilizing effect with respect to the dibenzoylmethane derivative.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

La présente invention concerne une composition cosmétique dans laquelle sont combinés un dérivé de dibenzoylméthane et un composé de phénol ou de bisphénol contenant du siloxane représenté par la formule suivante (I) ou (II). L'invention concerne également un procédé de photostabilisation, contre les rayonnements, d'au moins un dérivé de dibenzoylméthane avec au moins un dérivé de phénol ou de bisphénol contenant du siloxane représenté par la formule (I) ou (II). La présente invention concerne en outre l'utilisation dudit dérivé de phénol ou de bisphénol contenant du siloxane représenté par la formule (I) ou (II) dans une composition contenant, dans un véhicule acceptable d'un point de vue cosmétique, au moins un agent de criblage des rayons U.V.A. du dérivé de dibenzoylméthane de type 2, afin d'améliorer l'efficacité de ladite composition contre les rayons U.V.A.
PCT/EP2006/070078 2006-01-12 2006-12-21 Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé de phénol ou de bisphénol contenant du siloxane, et procédé de photostabilisation du dérivé de dibenzoylméthane WO2007080052A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008079358A1 (fr) * 2006-12-22 2008-07-03 Momentive Performance Materials Inc. Polymères de polycarbonate silylés, leur procédé de fabrication et articles formés à partir de ces polymères
WO2011004133A2 (fr) 2009-07-10 2011-01-13 L'oreal Materiau composite comprenant des filtres uv et des particules plasmoniques et utilisation en protection solaire.
FR2949332A1 (fr) * 2009-08-28 2011-03-04 Oreal Composition contenant un filtre dibenzoylmethane, un compose phenol ou bis-phenol et une s-triazine siliciee ; procede de photostabilisation du filtre dibenzoylmethane
WO2019093019A1 (fr) * 2017-11-13 2019-05-16 信越化学工業株式会社 Produit cosmétique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528380A1 (fr) * 1991-08-16 1993-02-24 Shiseido Company Limited Dérivé de silicone à fonction alcoyle-aryl 1,3-propanedione et agent de traitement externe de la peau contenant ce dérivé
EP0982310A1 (fr) * 1998-08-21 2000-03-01 L'oreal Procédé de photostabilisation de filtres solaires dérivés du dibenzoylméthane, compositions cosmétiques filtrantes photostabilisées ainsi obtenues et leurs utilisations.
WO2002049594A2 (fr) * 2000-12-18 2002-06-27 L'oreal Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528380A1 (fr) * 1991-08-16 1993-02-24 Shiseido Company Limited Dérivé de silicone à fonction alcoyle-aryl 1,3-propanedione et agent de traitement externe de la peau contenant ce dérivé
EP0982310A1 (fr) * 1998-08-21 2000-03-01 L'oreal Procédé de photostabilisation de filtres solaires dérivés du dibenzoylméthane, compositions cosmétiques filtrantes photostabilisées ainsi obtenues et leurs utilisations.
WO2002049594A2 (fr) * 2000-12-18 2002-06-27 L'oreal Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008079358A1 (fr) * 2006-12-22 2008-07-03 Momentive Performance Materials Inc. Polymères de polycarbonate silylés, leur procédé de fabrication et articles formés à partir de ces polymères
US8536282B2 (en) * 2006-12-22 2013-09-17 Momentive Performance Materials Inc. Silylated polycarbonate polymers, method of making, and articles
WO2011004133A2 (fr) 2009-07-10 2011-01-13 L'oreal Materiau composite comprenant des filtres uv et des particules plasmoniques et utilisation en protection solaire.
FR2949332A1 (fr) * 2009-08-28 2011-03-04 Oreal Composition contenant un filtre dibenzoylmethane, un compose phenol ou bis-phenol et une s-triazine siliciee ; procede de photostabilisation du filtre dibenzoylmethane
WO2019093019A1 (fr) * 2017-11-13 2019-05-16 信越化学工業株式会社 Produit cosmétique
JP2019089721A (ja) * 2017-11-13 2019-06-13 信越化学工業株式会社 化粧料
CN111343967A (zh) * 2017-11-13 2020-06-26 信越化学工业株式会社 化妆品

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