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WO2008064979A2 - Compositions cosmétiques contenant un dérivé d'arylalkyl benzoate amide contenant du siloxane; utilisation dudit dérivé comme solvant dans les huiles; nouveaux dérivés d'arylalkyl benzoate ester ou amide contenant du siloxane - Google Patents

Compositions cosmétiques contenant un dérivé d'arylalkyl benzoate amide contenant du siloxane; utilisation dudit dérivé comme solvant dans les huiles; nouveaux dérivés d'arylalkyl benzoate ester ou amide contenant du siloxane Download PDF

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Publication number
WO2008064979A2
WO2008064979A2 PCT/EP2007/061996 EP2007061996W WO2008064979A2 WO 2008064979 A2 WO2008064979 A2 WO 2008064979A2 EP 2007061996 W EP2007061996 W EP 2007061996W WO 2008064979 A2 WO2008064979 A2 WO 2008064979A2
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radical
formula
derivatives
triazine
chosen
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WO2008064979A3 (fr
Inventor
Didier Candau
Benoit Muller
Hervé Richard
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LOreal SA
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LOreal SA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • 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
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen

Definitions

  • the invention relates to a composition
  • a composition comprising, in a cosmetically acceptable medium, at least one specific siloxane-containing arylalkyl benzoate amide derivative of formula (I) , the definition of which will be given hereinafter .
  • composition comprising, in a cosmetically acceptable medium, at least one specific siloxane-containing arylalkyl benzoate amide derivative of formula (I) , characterized in that it contains at least one liquid fatty phase and a low- solubility lipophilic active agent.
  • the present invention relates to the use of at least one specific siloxane-containing arylalkyl benzoate amide derivative of formula (I) , the definition of which will be given hereinafter, in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one low- solubility lipophilic active agent, as solvent for said active agent in said liquid fatty phase, and in particular as solvent for organic UV screening agents that are not readily soluble.
  • the present invention also relates to novel specific siloxane-containing arylalkyl benzoate amide compounds of formula (I) .
  • cosmetic or dermatological products are provided in various galenical forms comprising a liquid fatty phase, such as dispersions, oily lotions, oil/water, water/oil or multiple emulsions, or cream gels.
  • Certain cosmetic or dermatological active agents that are particularly advantageous, such as lipophilic organic screening agents that are not readily soluble in the oily phase of these formulations, have a tendency, during storage, to form crystals or to precipitate, in particular in emulsions.
  • low-solubility lipophilic active agents such as the active agents chosen from aminophenol derivatives, salicylic acid derivatives, 2-amino-4- alkylaminopyrimidine 3 -oxide derivatives, in particular
  • dehydroepiandrosterone chemical derivatives and precursors thereof, such as 7 -hydroxy- or 7-keto-DHEA, or else 3 ⁇ -acetoxy-7-keto-DHEA, cholesterol and esters thereof, plant sterols such as phytosterols and sitosterols and esters thereof, pentacyclic triterpene acids, hydroxystilbenes, isoflavonoids, lipophilic organic UV screening agents with low solubility in antisun formulations, retinol and derivatives thereof, carotenoids such as lycopene, and also fragrances, essential oils, hormones, vitamins, in particular vitamin E, ceramides, or mixtures thereof.
  • antisun compositions are often in the form of an oil-in-water or water-in-oil emulsion, of gels or of anhydrous products which contain, at various concentrations, one or more lipophilic and/or hydrophilic, insoluble and/or soluble, organic and/or inorganic screening agents, capable of selectively absorbing harmful UV radiation.
  • screening agents and the amounts thereof are selected according to the desired protection factor.
  • the screening agents can distribute, respectively, either into the fatty phase or into the aqueous phase of the final composition.
  • certain organic UV screening agents are particularly advantageous, for instance s-triazine derivatives, since they are highly active in the UV-B range and the UV-A range depending on the substituents grafted onto the triazine ring, and generally exhibit good photostability .
  • dibenzoylmethane derivatives in particular 4-(tert- butyl) -4 ' -methoxydibenzoylmethane
  • benzophenone derivatives such as benzophenone-3
  • oils such as oxyethylenated or oxypropylenated fatty (mono/poly) alcohols ("Cetiol HE” from Henkel or “Witconol APM” from Witco) or else fatty esters such as Ci 2 -Ci 5 alkyl benzoate (“Finsolv TN” from Finetex) , or amino acid derivatives (“Eldew SL205” from Ajinomoto), because the solubility of these screening agents in these commonly used oils is insufficient.
  • oils such as oxyethylenated or oxypropylenated fatty (mono/poly) alcohols (“Cetiol HE” from Henkel or “Witconol APM” from Witco) or else fatty esters such as Ci 2 -Ci 5 alkyl benzoate (“Finsolv TN” from Finetex) , or amino acid derivatives (“Eldew SL205” from Ajinomoto), because the solubility of these screening
  • the present invention therefore relates to a composition
  • a composition comprising, in a cosmetically acceptable medium, at least one specific siloxane-containing arylalkyl benzoate amide derivative of formula (I) , the definition of which will be given hereinafter.
  • the present invention relates in particular to a composition
  • a composition comprising, in a cosmetically acceptable medium, at least one specific siloxane-containing arylalkyl benzoate ester or amide derivative of formula
  • (I) characterized in that it contains at least one liquid fatty phase and a low-solubility lipophilic active agent.
  • the present invention also relates to the use of at least one specific siloxane-containing arylalkyl benzoate amide derivative of formula (I) , the definition of which will be given hereinafter, in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one low-solubility lipophilic active agent, as solvent for said active agent in said liquid fatty phase, and in particular as sole solvent for said active agent.
  • the present invention also relates to the use of at least one derivative of formula (I) in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one low- solubility lipophilic active agent, for the purpose of improving the effectiveness of said active agent and/or the cosmetic qualities and/or the stability of said composition.
  • the present invention also relates to the use of at least one derivative of formula (I) in a composition comprising, in a cosmetically acceptable medium, at least one liquid fatty phase and at least one low- solubility lipophilic organic UV screening agent, for the purpose of improving the sun protection factor and/or the cosmetic qualities and/or the stability of this composition.
  • the present invention also relates to novel specific siloxane-containing arylalkyl benzoate amide compounds of formula (I) .
  • cosmetically acceptable is intended to mean compatible with the skin and/or its integuments, which has a pleasant colour, smell and feel and which does not generate any unacceptable discomfort (stinging, tautness, redness) that may dissuade the consumer from using this composition.
  • liquid fatty phase is intended to mean a fatty phase which is liquid at ambient temperature (25 0 C) and atmospheric pressure (760 mm Hg) , composed of one or more fatty substances that are liquid at ambient temperature, also known as oils, and that are compatible with one another.
  • lipophilic active agent is intended to mean any cosmetic or dermatological active agent capable of being completely dissolved in the molecular state in a liquid fatty phase or else of being solubilized in colloidal form (for example, in micellar form) in a liquid fatty phase.
  • low-solubility lipophilic active agent is intended to mean a lipophilic active agent which, at ambient temperature and in its preferred concentration range as specified below, has a phase that is insoluble in the oily phase of the composition, which limits its bioavailability and thus impairs the effectiveness of the composition.
  • siloxane-containing arylalkyl amide derivatives in accordance with the invention are chosen from those corresponding to general formula (I) below:
  • Ci-C 4 alkyl radical is a linear or branched Ci-C 4 alkyl radical
  • - p is 0 - 2
  • - m is 0 - 4
  • - X is -N(R 2 ) -
  • B is a divalent radical chosen from the group corresponding to one of the following formulae (II) , (III) and (IV) :
  • Z is a saturated or unsaturated, linear or branched Ci-C 6 alkylene radical optionally substituted with a hydroxyl radical or a saturated or unsaturated, linear or branched Ci-C 8 alkyl radical,
  • W represents a hydrogen atom, a hydroxyl radical or a saturated or unsaturated, linear or branched Ci-C 8 alkyl radical, v is 0 or 1.
  • the organosiloxane can contain units of formula (R) b -(Si) (0) ⁇ 4 -b) / 2 in which:
  • the - (Si) (R) a (0) (3 - a ) / 2 groups can be represented by formula (V) or (VI) below:
  • R 3 which may be identical or different, are chosen from linear or branched Ci-C 20 alkyl, phenyl, 3 , 3 , 3-trifluoropropyl and trimethylsilyloxy radicals, at least 80% by number of the R 3 radicals being methyl,
  • linear or cyclic diorganosiloxanes of formula (V) or (VI) which fall within the context of the present invention are random oligomers or polymers preferably having at least one, and even more preferably all, of the following characteristics:
  • the SiH groups may be present in the chain and/or at the ends of the chain. These SiH-containing derivatives are well-known products in the silicone industry and are generally commercially available. They are, for example, described in United States Patents US 3220972, US 3697473 and US 4340709.
  • the derivatives of formula (I) in accordance with the invention are preferably present in the compositions of the invention at contents ranging from 1% to 30% by weight, and more preferably from 3% to 20% by weight, relative to the total weight of the composition.
  • the derivative (s) of formula (I) in accordance with the invention is (are) preferably present in an amount sufficient to solubilize, by itself or by themselves (without it being necessary to use another solvent) , the total amount of active agent (s) not readily soluble that is (are) present in the composition.
  • the lipophilic active agents are of low solubility when they exhibit, at ambient temperature and in their preferred concentration range as specified below, a phase which is insoluble in the oily phase of the composition, which limits their bioavailability and thus impairs the effectiveness of the composition.
  • the low-solubility lipophilic active agents in accordance with the invention are preferably chosen from aminophenol derivatives, salicylic acid derivatives, 2-amino-4-alkylaminopyrimidine 3 -oxide derivatives, in particular 2-amino-4-dodecylamino- pyrimidine 3-oxide, DHEA (dehydroepiandrosterone) , chemical derivatives and precursors thereof such as 7 -hydroxy- or 7-keto-DHEA, or else 3 ⁇ -acetoxy-7-keto- DHEA, cholesterol and esters thereof, plant sterols such as phytosterols and sitosterols and esters thereof, pentacyclic triterpene acids, hydroxy- stilbenes, isoflavonoids, low-solubility lipophilic organic UV screening agents, retinol and derivatives thereof, carotenoids such as lycopene, and also fragrances, essential oils, hormones, vitamins, in particular vitamin E, ceramides, or mixtures thereof
  • aminophenol derivatives used are more particularly the derivatives of formula (I) below:
  • R' is a radical chosen from the group made up of the following radicals (a) , (b) and (c) :
  • R 1 represents a hydrogen atom or an optionally hydroxylated, saturated or unsaturated, linear or branched Ci to C 6 alkyl radical
  • R 2 represents a hydrogen atom or a radical chosen from saturated or unsaturated, linear, cyclic or branched Ci 2 to C 30 alkyl radicals, which is optionally hydroxylated, and
  • R 3 represents a radical chosen from saturated or unsaturated, linear, cyclic or branched, including condensed polycyclic, Ci 2 to C 30 alkyl radicals, which are optionally hydroxylated.
  • R 2 or R 3 radicals containing from 1 to 30 carbon atoms mention may advantageously be made of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl , octyl, nonyl , 2-ethylhexyl, dodecyl , hexadecyl , behenyl , octadecyl and 2-butyloctyl radicals.
  • These radicals preferably contain from 1 to 12 carbon atoms. Even more preferably, the alkyl radical generally contains from 1 to 6 carbon atoms.
  • As lower alkyl radical mention may be made of methyl, ethyl, propyl, isopropyl, tert-butyl and hexyl radicals.
  • a radical having one or more ethylenic unsaturations such as more particularly the allyl radical, is preferred.
  • alkyl radical is cyclic
  • the radical When it is hydroxylated, the radical preferably contains from 1 to 6 carbon atoms and from 1 to 5 hydroxyl groups.
  • a radical preferably containing 1 or 3 carbon atoms, in particular the hydroxymethyl , 2-hydroxyethyl , 2-hydroxypropyl or 3-hydroxypropyl radical is preferred.
  • a radical containing from 3 to 6 carbon atoms and from 2 to 5 hydroxyl groups such as the 2 , 3-dihydroxypropyl, 2 , 3 , 4-trihydroxybutyl , 2 , 3 , 4 , 5-tetrahydroxypentyl or 2, 3, 4, 5, 6-pentahydroxyhexyl radical is preferred.
  • alkoxylated radicals are alkyl radicals, as in particular described above, preceded by an oxygen atom.
  • the aminophenol derivatives used in the present application are those for which at least one and preferably all the conditions below are met: - the -OH function on the phenyl radical is in the ortho-position or, advantageously, in the para- position, - R' is chosen from a radical of formula (a) or (b) .
  • linear or branched alkyl radicals R 1 mention may be made of methyl, ethyl, propyl, isopropyl, tert- butyl or hexyl radicals.
  • the aminophenol derivative preferably used in said composition is a para-aminophenol derivative; even more preferably, it is N-ethoxycarbonyl -4 -para-aminophenol of formula (Ia) :
  • N-cholesteryloxycarbonyl -4 -para-aminophenol of formula (Ib) is N-cholesteryloxycarbonyl -4 -para-aminophenol of formula (Ib) :
  • the compounds with a long hydrocarbon-based chain are insoluble in oils, due to their steric hindrance, and have a tendency to recrystallize from water .
  • compositions according to the present invention comprising such an aminophenol derivative can be used as a depigmenting or bleaching agent in a cosmetic and/or dermatological composition.
  • these compositions will be used for treating regional hyperpigmentations caused by melanocyte hyperactivity, such as idiopathic melasmas which occur in the course of pregnancy ("pregnancy mask” or chloasma) or of oestroprogestative contraception, localized hyper- pigmentations caused by benign melanocyte proliferation and hyperactivity, such as senile pigmentation blemishes known as actinic lentigo, accidental hyperpigmentations or depigmentations, possibly caused by post-lesional cicatrization and photosensitization, and also certain leucodermias such as vitiligo.
  • melanocyte hyperactivity such as idiopathic melasmas which occur in the course of pregnancy ("pregnancy mask" or chloasma) or of oestroprogestative contraception
  • the concentration of aminophenol derivatives of the composition according to the present invention is from 0.001% to 30%, more preferably from 0.001% to 15%, even more preferably from 0.1% to 5% by weight.
  • the amount of amino acid esters will depend on the amount of aminophenol derivatives to be solubilized and may be between 0.01% and 90% by weight, and preferably between 0.1% and 60% by weight, relative to the total weight of the composition.
  • the low-solubility salicylic acid derivatives are the derivatives of formula
  • R"i represents a hydroxyl radical or an ester of formula
  • R" 4 is a saturated or unsaturated aliphatic radical containing from 1 to 26 carbon atoms, and preferably from 1 to 18 carbon atoms, or an amine or thiol function optionally substituted with an alkyl radical containing from 1 to 18 carbon atoms, and preferably from 1 to 12 carbon atoms
  • R" 2 and R" 3 independently of one another, are in the 3-, 4-, 5- or 6 -position on the benzene ring and represent, independently of one another, a hydrogen atom or a radical :
  • n and m independently of one another, are each an integer equal to 0 or 1, provided that R" 2 and R"3 are not simultaneously hydrogen atoms, and R" 5 represents a hydrogen, a linear, branched or cyclized, saturated aliphatic radical containing from 1 to 18 carbon atoms, or an unsaturated radical containing from 3 to 18 carbon atoms, bearing one to nine conjugated or unconjugated double bonds, it being possible for the radicals to be substituted with at least one substituent chosen from halogen atoms
  • the salicylic acid derivative is such that R" 5 represents a saturated aliphatic radical containing from 3 to 15 carbon atoms.
  • the salicylic acid derivative is such that R"i represents a hydroxyl radical.
  • the salicylic acid derivative is such that R" 5 is in the 5-position on the benzene ring and R" 2 represents a hydrogen atom.
  • the salicylic acid derivatives are derivatives of 5-n- octanoylsalicylic acid, 5-n-decanoylsalicylic acid, 5-n-dodecanoylsalicylic acid, 5-n-octylsalicylic acid, 5-n-heptyloxysalicylic acid, 4-n-heptyloxysalicylic acid, 5-tert-octylsalicylic acid, 3-tert-butyl-5- methsalicylic acid, 3-tert-butyl- ⁇ -methylsalicylic acid, 3 , 5-diisopropylsalicylic acid, 5-butoxysalicylic acid, 5-octyloxysalicylic acid, 5-propanoylsalicylic acid, 5-n-hexadecanoylsalicylic acid, 5-n-oleoyl- salicylic acid, 5-benzoylsalicylic acid, monovalent and
  • salicylic acid derivatives in topical compositions, for example, as a keratolytic agent for treating acne or as an anti -ageing agent;
  • Patent Applications FR-A-2 581 542 and EP-A-378 936 describe such derivatives.
  • Salicylic acid derivatives are highly advantageous in particular for preventing or repairing the principal manifestations of skin ageing, namely fine lines and wrinkles, disruption of the "grain" of the skin, modification of the complexion of the skin and loss of firmness and of tonicity of the skin.
  • the use of these derivatives poses a problem insofar as, when they are introduced without modification into topical compositions, they do not solubilize and remain in the crystalline state, rendering the use of the composition containing them ineffective for the treatment of the skin.
  • these derivatives are solubilized in lower alcohols, such as ethanol or isopropanol, or solvents such as octyldodecanol, certain glycols, or short-chain (less than Ci 2 ) fatty alcohols.
  • lower alcohols such as ethanol or isopropanol
  • solvents such as octyldodecanol, certain glycols, or short-chain (less than Ci 2 ) fatty alcohols.
  • these lower alcohols have the drawback of drying out and irritating the skin; it is therefore preferred to avoid using them in body and/or facial care products.
  • these solubilizing agents can only be introduced in small amounts otherwise they may impair the cosmetic qualities (drying out of the skin) and the stability of the compositions containing them.
  • the concentration of salicylic acid derivatives of the composition according to the present invention is preferably from 0.001% to 15% by weight, more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
  • the amount of amino acid esters will depend on the amount of salicylic acid derivatives to be solubilized. It may be from 0.01% to 90% by weight, and preferably between 0.1% and 60% by weight, relative to the total weight of the composition.
  • composition according to the invention comprising at least one salicylic derivative can be used as a cosmetic or dermatological composition, and in particular for caring for, protecting, cleansing and/or making up keratin materials of human beings (skin, lips, keratin fibres such as the hair and eyelashes) , and in particular for combatting the signs of skin ageing and/or for smoothing facial and/or body skin and/or for treating wrinkles and fine lines of the skin and/or for stimulating the process of epidermal renewal and/or for depigmenting or bleaching the skin and/or for treating acne and/or for treating skin disorders.
  • skin disorders is intended to mean in particular zona, burns, eczema, demodicidosis, skin ulcers, fibrosis, control of cicatrizations, psoriasis, pruritis, dermatitis, ichtyosis, corns and warts.
  • the derivatives of the 2-amino-4-alkylaminopyrimidine 3 -oxide family are the derivatives of general formula:
  • R 4 represents an alkyl group containing from 1 to 20 carbon atoms
  • Z' represents a hydrogen atom or an -OR 5 radical in which R 5 represents an alkyl group containing from 1 to 12 carbon atoms, and also its acylated forms or its addition salts with acids.
  • R 4 is chosen from the group made up of hexyl , heptyl , octyl, nonyl , decyl , undecyl and dodecyl radicals .
  • R 5 is chosen from the group made up of ethyl, propyl, butyl, pentyl and hexyl radicals.
  • the derivatives of the 2-amino-4-alkylaminopyrimidine 3 -oxide family can in particular be used in or for the preparation of a cosmetic or dermatological composition in accordance with the present invention for preventing and treating problems associated with sensitive skin and skin disturbances such as skin discomfort, tautness of the skin, skin itching, skin swelling, redness of the skin and heat sensation of the skin.
  • DHEA DHEA
  • DHEA or dehydroepiandrosterone also known as 3-beta- hydroxyandrost-5-en-17-one, or dehydroisoandrosterone, but also trans-dehydroandrosterone or prasterone, has the formula:
  • DHEA precursors to which the invention relates is intended to mean its biological precursors which are capable of being converted to DHEA during metabolism, and also its chemical precursors which can be converted to DHEA by exogenous chemical reaction.
  • biological precursors are ⁇ 5 -pregnenolone, 17 ⁇ -hydroxypregnenolone and 17 ⁇ -hydroxypregnenolone sulphate without this list being limiting.
  • chemical precursors of DHEA is intended to mean in particular saponins and their derivatives such as hecogenin ( (3beta, 5alpha, 23r)-3- hydroxyspirostan-12-one) and hecogenin acetate, diosgenin (5-spirosten-3beta-ol) , smilagenin and sarsapogenin, and also natural extracts containing them, in particular fenugreek and extracts of Dioscorea plants such as wild yam root, without this list being limiting .
  • saponins and their derivatives such as hecogenin ( (3beta, 5alpha, 23r)-3- hydroxyspirostan-12-one) and hecogenin acetate, diosgenin (5-spirosten-3beta-ol) , smilagenin and sarsapogenin, and also natural extracts containing them, in particular fenugreek and extracts of Dioscorea
  • DHEA derivatives is intended to mean both its metabolic derivatives and its chemical derivatives.
  • metabolic derivatives mention may in particular be made of ⁇ 5-androstene-3 , 17-diol, and in particular 5-androstene-3 ⁇ , 17 ⁇ -diol, ⁇ 4-androstene-3 , 17-dione, 7 -hydroxy-DHEA (7 ⁇ -hydroxy-DHEA or 7 ⁇ -hydroxy-DHEA) and 7-keto-DHEA, which is itself a metabolite of 7 ⁇ - hydroxy-DHEA, without this list being limiting.
  • 7 ⁇ -Hydroxy-DHEA is, with 5-androstene-3 ⁇ , 17 ⁇ -diol, a major metabolite of DHEA, obtained by the action of 7 ⁇ -hydroxylase on DHEA.
  • 7 ⁇ -Hydroxy-DHEA is a minor metabolite of DHEA, obtained by the action of 7 ⁇ -hydroxylase on DHEA.
  • the 7 -hydroxy-DHEA preferably used in the compositions according to the present invention is 7 ⁇ -hydroxy-DHEA.
  • a process for preparing this compound is described in Patent Applications FR 2 771 105 and WO 94/08688.
  • DHEA salts and in particular water-soluble salts such as DHEA sulphate,- DHEA esters such as esters of hydrocarboxylic acids and of DHEA, in particular those described in Patent US 5 736 537, or else DHEA salicylate, DHEA acetate, DHEA valerate (or n-heptanoate) and DHEA enanthate.
  • the concentration of DHEA-based compound in the composition according to the present invention can advantageously range from 0.001% to 30% by weight, preferably from 0.01% to 20%, and even more preferably from 0.01% to 10% by weight, relative to the total weight of the composition. These compounds will be in solubilized form between 2O 0 C and 9O 0 C.
  • low-solubility lipophilic organic UV screening agent is intended to mean any organic UV screening agent having a water-solubility of less than 0.1% by weight and a solubility of less than 15% by weight in most organic solvents, such as liquid paraffin, fatty alcohol benzoates and fatty acid triglycerides, for example Miglyol ® 812 sold by the company Dynamit Nobel.
  • This solubility, realized at 7O 0 C, is defined as the amount of product in solution in the solvent at equilibrium with an excess of solid in suspension after a return to ambient temperature. It can be readily evaluated in the laboratory.
  • low- solubility lipophilic organic screening agents used in the compositions of the invention, mention may in particular be made of: triazine derivatives; dibenzoylmethane derivatives; benzophenones .
  • the triazine derivatives may in particular be chosen from the 1 , 3 , 5-triazine derivatives of formula (2) below:
  • - X a which may be identical or different, represent oxygen or the -NH- radical
  • R - R a which may be identical or different, are chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals; a linear or branched Ci-Ci 8 alkyl radical; a C 5 -Ci 2 cycloalkyl radical optionally substituted with one or more Ci-C 4 alkyl radicals; a polyoxyethylenated radical comprising from 1 to 6 ethylene oxide units and the terminal OH group of which is methylated; a radical of formula (4) , (5) or (6) below:
  • R 4 is hydrogen or a methyl radical
  • R 5 is a Ci-C 9 alkyl radical; - q is an integer ranging from 0 to 3;
  • - r is an integer ranging from 1 to 10;
  • - A' is a C 4 -C 8 alkyl radical or a C 5 -C 8 cycloalkyl radical
  • - B' is chosen from: a linear or branched Ci-C 8 alkyl radical; a C 5 -C 8 cycloalkyl radical; an aryl radical optionally substituted with one or more Ci-C 4 alkyl radicals .
  • a first more particularly preferred family of 1 , 3 , 5-triazine derivatives in particular described in document EP-A-O 517 104, is that of the 1 , 3 , 5-triazines corresponding to formula (2) in which Ai, A 2 and A 3 are of formula (3) and have the following characteristics:
  • X a -R a radicals represents the -NH-R 3 radical with R a chosen from: a C 5 -Ci 2 cycloalkyl radical optionally substituted with one or more Ci-C 4 alkyl radicals; a radical of formula (4) , (5) or (6) above in which:
  • - B' is a Ci-C 4 alkyl radical
  • - R 5 is the methyl radical
  • X a -R a represent the -0-R a radical with R a , which may be identical or different, chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals; a linear or branched Ci-Ci 8 radical; a C 5 -Ci 2 cycloalkyl radical optionally substituted with one or more Ci-C 4 alkyl radicals; a radical of formula (4), (5) or (6) above in which: - B' is a Ci-C 4 alkyl radical;
  • R 5 is the methyl radical.
  • a second more particularly preferred family of 1, 3, 5-triazine derivatives in particular described in document EP-A-O 570 838, is that of the 1 , 3 , 5-triazines corresponding to formula (2) in which Ai, A 2 and A 3 are of formula (3) and have all of the following characteristics :
  • X a -R a represent the -NH-R 3 radical, with R a chosen from: a linear or branched Ci-Ci 8 alkyl radical; a C 5 -Ci 2 cycloalkyl radical optionally substituted with one or more Ci-C 4 alkyl radicals; a radical of formula (4), (5) or (6) above in which:
  • - B' is a Ci-C 4 alkyl radical
  • - R 5 is the methyl radical
  • the other or the two other X a -R a being the -0-R a radical with R a , which may be identical or different, chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals; a linear or branched Ci-Ci 8 alkyl radical; a C 5 -Ci 2 cycloalkyl radical optionally substituted with one or more Ci-C 4 alkyl radicals; a radical of formula (4), (5) or (6) above in which:
  • - B' is a Ci-C 4 alkyl radical
  • - R 5 is the methyl radical
  • a particularly preferred 1 , 3 , 5-triazine of this second family is 2- [p-tert-butylamido) anilino] -4 , 6-bis [p- (2 ' - ethylhexyl-1 ' -oxycarbonyl) anilino] -1,3, 5-triazine or "Diethylhexyl Butamido Triazone" sold under the trade name "Uvasorb HEB” by Sigma 3V and corresponding to the formula below:
  • R' denotes a 2-ethylhexyl radical and R" denotes a tert-butyl radical.
  • a third preferred family of compounds that can be used in the context of the present invention, and which is in particular described in document US 4,724,137, is that of the 1, 3 , 5-triazines corresponding to formula (2) in which A 1 , A 2 and A 3 are of formula (3) and have the following characteristics:
  • R - R a which may be identical or different, represent a C 6 -Ci 2 alkyl radical or a polyoxyethylenated radical comprising from 1 to 6 ethylene oxide units and the terminal OH group of which is methylated.
  • a particularly preferred 1 , 3 , 5-triazine of this third family is 2 , 4 , 6-tris [p- (2 ' -ethylhexyl-1 ' -oxycarbonyl) - anilino] -1 , 3 , 5-triazine or "Ethylhexyl Triazone” sold in particular under the trade name "Uvinul T 150" by the company BASF and corresponds to the formula below: in which R'" denotes a 2-ethylhexyl radical.
  • the triazine derivatives may also be chosen from the bisresorcinyltriazine derivatives, in accordance with the present invention, corresponding to formula (7) below:
  • R 6 and R 7 radicals which may be identical or different, denote a C 3 -Ci 8 alkyl radical; a C 2 -Ci 8 alkenyl radical or else a residue of formula
  • Tl is a hydrogen atom or a
  • Ci-C 8 alkyl radical Ci-C 8 alkyl radical
  • R 8 denotes a hydrogen atom, a Ci-Ci 0 alkyl radical, a radical of formula - (CH 2 CHRi 0 -0) niR 9 where rii is an integer from 1 to 16, or else a residue of structure -CH 2 -CH- (OH) -CH 2 OTl with Tl having the same meaning indicated above,-
  • R 9 denotes hydrogen, a metal cation M, a Ci-C 5 alkyl radical or a residue of formula -(CH 2 ) m2 -0Tl where m2 is an integer from 1 to 4 and Tl has the same meaning indicated above,-
  • - Ri o is hydrogen or methyl
  • the alkyl radicals are linear or branched and can be chosen, for example, from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl , isoamyl, tert-amyl, heptyl , octyl, isooctyl, nonyl , decyl , undecyl , dodecyl , tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl;
  • alkenyl radicals can be chosen, for example, from allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2 , 4-dienyl , 3-methylbut-2-enyl , 2-n-octenyl, 2-n-dodecenyl , isododecenyl or 4-n-octa- decenyl ;
  • alkoxy radicals are linear or branched and can be chosen, for example, from methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy;
  • Ci-C 5 monoalkylamino or dialkylamino radicals can be chosen, for example, from methylamino, ethylamino, propylamino, n-butylamino, sec-butylamino, tert-butyl - amino, pentylamino, dimethylamino, diethylamino, dibutylamino or methylethylamino;
  • the metal cations are alkali metal cations, alkaline earth metal cations or metal cations chosen, for example, from lithium, potassium, sodium, calcium, magnesium, copper and zinc.
  • the bisresorcinyltriazine derivatives of formula (7) of the invention are screening agents already known per se. They are described and prepared according to the syntheses indicated in Patent Application EP-A-0775 698.
  • the compound derived from bisresorcinyltriazine that is more particularly preferred according to the invention will be the compound 2 , 4-bis ⁇ [4- (2-ethylhexyloxy) -2- hydroxy] phenyl ⁇ -6- (4-methoxyphenyl) -1,3, 5-triazine (INCI name: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine) sold under the trade name "Tinosorb S" by Ciba Geigy.
  • dibenzoylmethane derivatives mention may in particular be made, in a nonlimiting manner, of:
  • benzophenone-1 sold under the trade name "Uvinul 400" by BASF
  • benzophenone-2 sold under the trade name "Uvinul D50” by BASF
  • benzophenone-3 or oxybenzone sold under the trade name
  • UV-24 by American Cyanamid, benzophenone- 12 , n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate sold under the name "Uvinul A+” by BASF.
  • one or more low- solubility UV screening agents will be chosen as low-solubility lipophilic active agent for the purpose of the invention.
  • the low-solubility lipophilic UV screening agent (s) is (are) preferably present in the compositions at contents which are generally from 0.01% to 10% by weight, and more preferably at contents of from 0.1% to 6% by weight, relative to the total weight of the composition.
  • the derivative (s) of formula (I) in accordance with the invention is (are) used as sole solvent for said active agent (s) that is (are) not readily soluble.
  • Another subject of the invention consists of the use of at least one derivative of formula (I) as defined above, in a cosmetic or dermatological photoprotective composition containing at least one liquid fatty phase and at least one low-solubility organic UV screening agent for the purpose of improving the sun protection factor and/or the cosmetic qualities and/or the stability of this composition.
  • compositions in accordance with the invention may also comprise other additional organic or inorganic UV screening agents that are active in the UVA range and/or the UVB range and 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; hydrosoluble benzophenone derivatives ⁇ , ⁇ -diphenyl acrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives, in particular those mentioned in Patent US 5 624 663; benzimidazole derivatives; imidazolines; bisbenzoazolyl derivatives as described in Patents EP 669323 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, GB 2303549, DE 197 26 184 and EP 893119; screening polymers and screening silicones such as those described in particular in Application WO 93/04665; dimers derived from ⁇ -alkylstyrene, such as those described in Patent Application DE 19855649;
  • Ethylhexyl Salicylate sold under the name "Neo Heliopan OS” by Haarmann and Reimer
  • Dipropyleneglycol Salicylate sold under the name
  • Neo Heliopan TS sold under the name Neo Heliopan TS” by Haarmann and Reimer
  • Octocrylene sold in particular under the trade name "UVINUL N539" by BASF
  • Etocrylene sold in particular under the trade name "Uvinul N35” by BASF
  • Benzophenone-4 sold under the trade name "Uvinul MS40" by BASF,
  • Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name "EUSOLEX 232" by Merck, Disodium Phenyl Dibenzimidazole Tetra-sulfonate sold under the trade name "Neo Heliopan AP” by Haarmann and Reimer,
  • Methyl anthranilate sold under the trade name "Neo Heliopan MA” Haarmann and Reimer,
  • Polyorganosiloxane comprising benzalmalonate functions such as Polysilicone-15 sold under the trade name "Parsol SLX” by Hoffmann La Roche,
  • the preferred additional organic photoprotective agents are chosen from:
  • the inorganic photoprotective agents are chosen from coated or uncoated metal oxide pigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) such as, for example pigments of titanium oxide (amorphous or crystallized in rutile and/or anatase form) , iron oxide, zinc oxide, zirconium oxide or cerium oxide, which are all UV photoprotective agents well-known per se .
  • the pigments may be coated or uncoated.
  • the coated pigments are pigments which 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, p. 53-64, such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal (titanium or aluminium) alkoxides, polyethylene, silicones, proteins (collagen, elastin) , alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate .
  • surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, p. 53-64 such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium,
  • silicones are organosilicon polymers or oligomers having a linear or cyclic structure, that are branched or crosslinked, of variable molecular weight, obtained by polymerization and/or polycondensation of appropriately functionalized silanes, and composed for the main part by a repetition of main units in which the silicon atoms are joined together by oxygen atoms (siloxane bond) , optionally substituted hydrocarbon-based radicals being directly bonded via a carbon atom to said silicon atoms.
  • silanes also encompasses the silanes required for their preparation, in particular, alkylsilanes .
  • the silicones used for coating pigments suitable for the present invention are preferably chosen from the group containing alkylsilanes, polydialkylsiloxanes and polyalkylhydrogensiloxanes . Even more preferably, the silicones are chosen from the group containing octyltrimethylsilane, polydimethylsiloxanes and polymethylhydrogensiloxanes .
  • the metal oxide pigments prior to their treatment with silicones, may have been treated by other surface agents, in particular by cerium oxide, alumina, silica, aluminium compounds, silicon compounds, or mixtures thereof.
  • the coated pigments are more particularly titanium oxides coated with: silica, such as the product “Sunveil” from Ikeda and the product “Eusolex T-AVO” from Merck; silica and iron oxide such as the product “Sunveil F” from Ikeda; silica and alumina such as the products “Microtitanium Dioxide MT 500 SA” and “Microtitanium Dioxide MT 100 SA” from Tayca, “Tioveil” from Tioxide and “Mirasun TiW 60" from Rhodia,- alumina such as the products “Tipaque TTO-55(B)” and “Tipaque TTO-55(A)” from Ishihara and "UVT 14/4" from Kemira; - alumina and aluminium stearate such as the product
  • titanium oxide pigments treated with a silicone are preferably TiO 2 treated with octyltrimethylsilane and of which the average size of the elemental particles is between 25 and 40 nm such as that sold under the trade name "T 805" by Degussa Silicas, TiO 2 treated with a polydimethylsiloxane and of which the average size of the elemental particles is 21 nm such as that sold under the trade name "70250 Cardre UF TiO2SI3" by Cardre, anatase/rutile TiO 2 treated with a polydimethylhydrogensiloxane and of which the average size of the elemental particles is 25 nm such as that sold under the trade name "Microtitanium Dioxide USP Grade Hydrophobic" by Color Techniques.
  • the uncoated titanium oxide pigments are, for example, sold by Tayca under the trade names "Microtitanium Dioxide MT 500 B", or “Microtitanium Dioxide MT 600 B", by Degussa under the name “P 25”, by Wacker under the name “Transparent Titanium Oxide PW” , by Miyoshi Kasei under the name “UFTR”, by Tomen under the name “ITS” and by Tioxide under the name "Tioveil AQ” .
  • the uncoated zinc oxide pigments are, for example: those sold under the name "Z-Cote” by Sunsmart; those sold under the name “Nanox” by Elementis; and - those sold under the name “Nanogard WCD 2025" by Nanophase Technologies .
  • coated zinc oxide pigments are, for example those sold under the name "Z-COTE HPl” by Sunsmart (dimethicone coated ZnO) ; those sold under the name “Oxide Zinc CS-5" by Toshiba (ZnO coated with polymethylhydrogensiloxane) ; those sold under the name “Nanogard Zinc Oxide FN” by Nanophase Technologies (as a 40% dispersion in “Finsolv TN", benzoate of Ci 2 -Ci 5 alcohols); those sold under the name "Daitopersion ZN-30" and
  • the uncoated cerium oxide pigments are sold, for example, under the name "Colloidal Cerium Oxide” by Rhone Poulenc .
  • the uncoated iron oxide nanopigments are, for example, sold by Arnaud under the names "Nanogard WCD 2002
  • the coated iron oxide pigments are, for example, sold by Arnaud under the names "Nanogard WCD 2008 (FE 45B FN)", “Nanogard WCD 2009 (FE 45B 556)", “Nanogard FE 45 BL 345", “Nanogard FE 45 BL” or by BASF under the name "Transparent Iron Oxide” .
  • the additional photoprotective agents are generally present in the compositions according to the invention in amounts 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 may 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
  • aqueous compositions conforming to the present invention may moreover comprise conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or non- ionic, hydrophilic or lipophilic thickeners, demulcents, humectants, opacifiers, stabilizers, emollients, silicones, anti- foaming agents, fragrances, preservatives, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants and basifying or acidifying agents, or any other ingredient commonly used in the cosmetics and/or dermatological field.
  • conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or non- ionic, hydrophilic or lipophilic thickeners, demulcents, humectants, opacifiers, stabilizers, emollients, silicones, anti- foaming agents, fragrances, preservatives, anionic,
  • the fatty substances may be composed of an oil or a wax other than the apolar waxes as defined previously or mixtures thereof.
  • oil is understood to mean a compound that is liquid at ambient temperature.
  • wax is understood to mean a compound that is solid or substantially solid at ambient temperature, and of which the melting point is generally greater than 35 0 C.
  • oils mention may be made of mineral oils (paraffin); vegetable oils (sweet almond oil, macadamia oil, blackcurrant seed oil, jojoba oil) ; synthetic oils such as perhydrosqualene, alcohols, fatty amides (such as isopropyl lauroyl sarcosinate sold under the name "Eldew SL-205" by Ajinomoto), fatty acids or esters such as the benzoate of Ci 2 -Ci 5 alcohols sold under the trade name "Finsolv TN" or "Witconol TN” by Witco, 2- ethylphenyl benzoate such as the commercial product sold under the name X-Tend 226 ® by ISP, octyl palmitate, isopropyl lanolate, triglycerides, including those of capric/caprylic acids, dicaprylyl carbonate sold under the name "Cetiol CC" by Cognis, oxyethylenated or
  • waxy compounds mention may be made of carnauba wax, beeswax, hydrogenated castor oil, polyethylene waxes and polymethylene waxes such as that sold under the name "Cirebelle 303" by Sasol .
  • the lower polyols may be chosen from glycols and glycol ethers such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol and diethylene glycol .
  • carboxyvinyl polymers such as carbopols (carbomers) and pemulens (acrylate/Ci O -C 3 o alkyl acrylate copolymers) ; polyacrylamides such as for example the crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide/Ci 3 _i 4 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyltaurate copolymer/isohexadecane/ polysorbate 80) by Seppic,- polymers and copolymers of 2-acrylamido-2-methylpropanesulphonic acid optionally crosslinked and/or neutralized, such as poly (2- acrylamido-2-methylpropanesulphonic acid) sold by Hoechst under the trade name "Hostacerin AMPS" (CTFA name: ammonium polyacryloyldimethyl taurate) or
  • lipophilic thickeners mention may be made of synthetic polymers such as poly (Ci 0 -C 30 alkyl acrylates) sold under the name “Intelimer IPA 13-1" and “Intelimer IPA 13-6” by Landec or else modified clays such as hectorite and its derivatives, such as the products sold under the name “Bentone” .
  • synthetic polymers such as poly (Ci 0 -C 30 alkyl acrylates) sold under the name "Intelimer IPA 13-1" and “Intelimer IPA 13-6” by Landec or else modified clays such as hectorite and its derivatives, such as the products sold under the name “Bentone” .
  • active ingredients mention may be made of: - vitamins (C, K, PP, etc.) and their derivatives or precursors, alone or as mixtures; agents for combatting pollution and/or free- radical scavengers; depigmenting agents and/or propigmenting agents,- - anti-glycation agents,- soothing agents,-
  • NO- synthase inhibitors agents that stimulate the synthesis of dermal or epidermal macromolecules and/or that prevent their degradation; agents that stimulate fibroblast proliferation,- agents that stimulate keratinocyte proliferation,- myo relaxants; tensioning agents,- - mattifying agents,- keratolytic agents,- desquamating agents,- moisturisers,- anti- inflammatory agents,- - agents that act on the energy metabolism of cells,- insect repellents; substance P antagonists or CRGP antagonists; agents for preventing hair loss and/or for regrowth; and - anti-wrinkle agents.
  • compositions according to the invention may be prepared according to the techniques well known to a person skilled in the art. They may be, in particular in the form of a simple or complex (0/W, W/0, 0/W/O or W/O/W) emulsion such as a cream, a milk or a cream-gel; in the form of an aqueous gel; or in the form of a lotion. They may also be packaged in an aerosol and be in the form of a foam or spray.
  • 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 in an appropriate manner according to the emulsion to be obtained (W/0 or 0/W) .
  • the emulsions may also contain other types of stabilizers such as for example fillers, gelling polymers or thickeners.
  • emulsifying surfactants that can be used for preparing W/0 emulsions, mention may be made, for example, of alkyl esters or ethers of sorbitan, of glycerol or of sugars,- silicone surfactants, for example dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol sold under the name "DC 5225 C” by Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid” by Dow Corning; cetyl dimethicone copolyol such as the product sold under the name "Abil EM 9OR” by Goldschmidt and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 mol) and hexyl laurate sold under the name "Abil WE 09" by Goldschmid
  • alkylated polyol esters mention may be made especially of polyethylene glycol esters, for example PEG-30 dipolyhydroxystearate such as the product sold under the name "Arlacel P135" by ICI.
  • glycerol and/or sorbitan esters mention may be made for example of polyglycerol isostearate such as the product sold under the name "Isolan GI 34" by Goldschmidt; sorbitan isostearate, such as the product sold under the name “Arlacel 987” by ICI; sorbitan isostearate and glycerol such as the product sold under the name “Arlacel 986” by ICI, and mixtures thereof.
  • emulsifiers for example as emulsifiers, of non-ionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid and glycerol esters,- oxyalkylenated fatty acid and sorbitan esters,- oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters such as the PEG-100 stearate/glyceryl stearate mixture sold, for example by ICI under the name "Arlacel 165",- oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers,- sugar esters such as sucrose stearate; fatty alcohol and sugar ethers, especially alkylpolyglucosides (APGs) such as decyl glucoside and lauryl glucoside sold, for example,
  • APGs alkylpoly
  • the mixture of alkyl polyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, as described, for example, in document WO-A-92/06778.
  • emulsion stabilizers use will more particularly be made of the polymers of isophthalic acid or sulphoisophthalic acid, and in particular phthalate/sulphoisophthalate/glycol copolymers, for example, the diethylene glycol/phthalate/isophthalate/
  • the aqueous phase of the latter may comprise a non-ionic vesicular dispersion prepared according to known processes (Bangham,
  • compositions according to the invention find their application in a large number of treatments, in particular cosmetic treatments, for the skin, lips and hair, including the scalp, in particular for protecting and/or caring for the skin, lips and/or hair, and/or for making up the skin and/or the lips.
  • compositions according to the invention for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and/or scalp, in particular care products, sunscreen products and makeup products.
  • the cosmetic compositions according to the invention may, for example, be used as a makeup product.
  • the cosmetic compositions according to the invention may, for example, be used as a care product and/or 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 in an aerosol and may be in the form of a foam or spray.
  • compositions according to the invention in the form of vaporizable fluid lotions in accordance with the invention are applied to the skin or the hair in the form of fine particles using pressurized devices.
  • the devices in accordance with the invention are well known to those skilled in the art and comprise non-aerosol pump-dispensers or "atomizers", aerosol containers comprising a propellant and also aerosol pump- dispensers that use compressed air as a propellant. The latter 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.
  • 3-Aminopropylmethylbis (trimethylsiloxy) silane (5.25 g, 0.019 mol) solubilized in 10 ml of anhydrous dichloromethane, and then diisopropylethylamine (9.5 ml, 0.057 mol) were added dropwise thereto. After the solvent had been evaporated off under vacuum, the orangey oil obtained was taken up in 100 ml of ethyl acetate. After two washes of the organic phase with water and then with a saturated solution of sodium chloride, it was dried over sodium sulphate.
  • 3-Amino- propylmethylbis (trimethylsiloxy) silane (20.48 g, 0.0732 mol) solubilized in 40 ml of anhydrous acetonitrile, and then diisopropylethylamine (37 ml, 0.219 mol) were added dropwise thereto. After the solvent had been evaporated off under vacuum, the orangey oil obtained was taken up in 300 ml of ethyl acetate. After 2 washes of the organic phase with water and then with a saturated solution of sodium chloride, it was dried over sodium sulphate.
  • phase B The aqueous phase (phase B) containing all its ingredients was heated to 8O 0 C in a waterbath.
  • the fatty phase (phase A) containing all its ingredients was heated to 8O 0 C in a waterbath.
  • A was emulsified in B with rotor-stator stirring (apparatus from the company Moritz) .
  • Phase C was incorporated and the mixture was left to return to ambient temperature with moderate stirring.
  • the triethanolamine was introduced so as to adjust the pH to the desired value at the end of manufacture.
  • the sunscreen emulsions obtained are stable with respect to storage and do not exhibit any crystals or precipitates .

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Abstract

L'invention porte sur une composition comportant, dans un milieu acceptable du point de vue cosmétique, au moins un dérivé spécifique d'arylalkyl benzoate amide contenant du siloxane représenté par la formule (I) ci-après : (I) et, plus particulièrement, sur une composition comportant, dans un milieu acceptable du point de vue cosmétique, au moins une phase grasse liquide et au moins un agent actif lipophile de solubilité faible, en particulier, un agent de criblage organique lipophile de solubilité faible, tel que les dérivés de triazine, les dérivés de dibenzoylméthane ou les dérivés de benzophénone. La présente invention porte sur l'utilisation d'au moins un dérivé spécifique d'arylalkyl benzoate amide contenant du siloxane représenté par la formule (I) dans une composition comportant, dans un milieu acceptable du point de vue cosmétique, au moins une phase grasse liquide et au moins un agent actif lipophile tel que mentionné ci-dessus, comme solvant pour ledit agent actif dans ladite phase grasse liquide, et également dans l'objectif d'améliorer l'efficacité dudit agent actif lipophile et/ou les qualités cosmétiques et/ou la stabilité de ladite composition. La présente invention porte également sur de nouveaux composés d'arylalkyl benzoate amide contenant du siloxane représentés par la formule (I).
PCT/EP2007/061996 2006-11-27 2007-11-07 Compositions cosmétiques contenant un dérivé d'arylalkyl benzoate amide contenant du siloxane; utilisation dudit dérivé comme solvant dans les huiles; nouveaux dérivés d'arylalkyl benzoate ester ou amide contenant du siloxane Ceased WO2008064979A2 (fr)

Applications Claiming Priority (4)

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FR0655122 2006-11-27
FR0655122A FR2908993A1 (fr) 2006-11-27 2006-11-27 Compositions cosmetiques contenant un derive ester ou amide d'arylalkyl benzoate siloxanique ; utilisation dudit derive comme solvant dans les huiles ; nouveaux derives esters ou amides d'arylalkyl benzoate siloxaniques.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9265708B2 (en) 2012-09-24 2016-02-23 Ajinomoto Co., Inc. Liquid cleanser comprising sterol ester and C5-6 hydroxyalcohol
WO2017003685A1 (fr) * 2015-06-30 2017-01-05 Elevance Renewable Sciences, Inc. Composés photostabilisants et procédés de fabrication et d'utilisation de ceux-ci

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2929829A (en) * 1956-10-12 1960-03-22 Union Carbide Corp Organosilicon acylamino compounds and process for producing the same
JPS60258260A (ja) * 1984-06-01 1985-12-20 Shin Etsu Chem Co Ltd 室温硬化性シリコ−ンゴム組成物
US4608270A (en) * 1985-10-25 1986-08-26 Dow Corning Corporation Acylamino silicon compounds, their use and preparation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9265708B2 (en) 2012-09-24 2016-02-23 Ajinomoto Co., Inc. Liquid cleanser comprising sterol ester and C5-6 hydroxyalcohol
WO2017003685A1 (fr) * 2015-06-30 2017-01-05 Elevance Renewable Sciences, Inc. Composés photostabilisants et procédés de fabrication et d'utilisation de ceux-ci

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