WO2012119860A1 - Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé monoester-monoamide d'acide méthylsuccinique; procédé de photostabilisation d'un dérivé de dibenzoylméthane - Google Patents

Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé monoester-monoamide d'acide méthylsuccinique; procédé de photostabilisation d'un dérivé de dibenzoylméthane Download PDF

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WO2012119860A1
WO2012119860A1 PCT/EP2012/053066 EP2012053066W WO2012119860A1 WO 2012119860 A1 WO2012119860 A1 WO 2012119860A1 EP 2012053066 W EP2012053066 W EP 2012053066W WO 2012119860 A1 WO2012119860 A1 WO 2012119860A1
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PCT/EP2012/053066
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Hervé Richard
Benoit Muller
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L'oreal
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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

  • the present invention relates to a cosmetic composition containing the combination of at least one screening agent of the dibenzoylmethane derivative type and of at least one monoester-monoamide compound of methylsuccinic acid.
  • the invention also relates to a process for radiation-photostabilizing at least one screening agent of the dibenzoylmethane derivative type with a monoester- monoamide compound of methylsuccinic acid of formula (I), the definition of which will be given hereinbelow.
  • the present invention also relates to the use of at least one monoester- monoamide compound of methylsuccinic acid of formula (I) in a composition comprising, in a cosmetically acceptable support, at least one dibenzoylmethane derivative, for the purpose of improving the efficacy of said composition with respect to UV-A rays.
  • UV-B radiation It is known that light radiation with wavelengths of between 280 nm and 400 nm permits tanning of the human epidermis and that light rays with wavelengths more particularly between 280 nm and 320 nm, known as UV-B rays, cause skin burns and erythema which can harm the development of a natural tan. For these reasons, and also for aesthetic reasons, there is constant demand for means for controlling this natural tanning in order thus to control the colour of the skin; this UV-B radiation should thus be screened out.
  • UV-A rays with wavelengths between 320 and 400 nm, which cause tanning of the skin, are liable to induce adverse changes therein, in particular in the case of sensitive skin or skin that is continually exposed to solar radiation.
  • UV-A rays cause in particular a loss of elasticity of the skin and the appearance of wrinkles leading to premature ageing of the skin. They promote triggering of the erythemal reaction or amplify this reaction in certain individuals and may even be the cause of phototoxic or photoallergic reactions.
  • people increasingly wish to control the effect of UV-A rays on their skin. It is thus desirable also to screen out UV-A radiation.
  • antisun compositions comprising organic screening agents that are active in the UV-A region and in the UV-B region are generally used.
  • the majority of these screening agents are liposoluble.
  • one particularly advantageous family of UV-A screening agents is currently constituted of dibenzoylmethane derivatives, and in particular 4-fe/f-butyl- 4'-methoxydibenzoylmethane, which specifically have a high intrinsic absorption power.
  • dibenzoylmethane derivatives which are products that are now well known per se as screening agents that are active in the UV-A range, are described in particular in French patent applications FR-A-2 326 405 and FR-A-2 440 933, and also in European patent application EP-A-0 1 14 607; 4-fe/f-butyl-4'- methoxydibenzoylmethane is moreover currently sold under the trade name Parsol 1789® by the company DSM Nutritional Products.
  • dibenzoylmethane derivatives are products that are relatively sensitive to ultraviolet radiation (especially UV-A radiation), i.e., more specifically, they have an annoying tendency to be degraded more or less rapidly under the action of the latter.
  • UV-A radiation especially UV-A radiation
  • this substantial lack of photochemical stability of dibenzoylmethane derivatives towards ultraviolet radiation, to which they are by nature intended to be subjected does not make it possible to guarantee constant protection during prolonged exposure to the sun, so that repeated applications at regular and close intervals of time have to be carried out by the user in order to obtain effective protection of the skin against UV-A rays.
  • the Applicant has now discovered, surprisingly, that by combining the dibenzoylmethane derivatives mentioned above with an effective amount of a monoester-monoamide compound of methylsuccinic acid of formula (I) that will be defined in detail below, it is possible to substantially and appreciably further improve the photochemical stability (or photostability) of these same dibenzoylmethane derivatives and their efficacy in the UV-A range. Compositions containing such a combination also result, after application, in a more uniform distribution of the UV-Screening agent.
  • the compounds of formula (I) also have the advantage of being able to be incorporated in the formulations without destabilizing them.
  • 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 towards UV radiation of at least one UV-A screening agent of dibenzoylmethane derivative type that consists in combining with said dibenzoylmethane derivative at least one monoester-monoamide compound of methylsuccinic acid of formula (I), the definitions of which will be given hereinbelow.
  • another subject of the present invention is the use of a monoester- monoamide compound of methylsuccinic acid of formula (I) in a composition comprising, in a cosmetically acceptable support, at least one dibenzoylmethane derivative, for the purpose of improving the efficacy of said composition with respect to UV-A rays.
  • cosmetically acceptable means compatible with the skin and/or its integuments, having a pleasant colour, odour and feel and not causing any unacceptable discomfort (stinging, tautness or redness) liable to discourage the consumer from using this composition.
  • dibenzoylmethane derivatives that may especially be mentioned, in a non-limiting manner, are:
  • the dibenzoylmethane derivative(s) may be present in the compositions in accordance with the invention in contents preferably ranging from 0.01 % to 20% by weight and more preferentially from 0.1 % to 10% by weight and more preferentially still from 0.1 % to 6% by weight relative to the total weight of the composition.
  • Ri and R 2 which are identical or different, denote a linear or branched C1-C20 alkyl radical, or a C5-C6 cycloalkyl radical, optionally substituted with one or more identical or different C1-C3 alkyl radicals,
  • X and Y denote, independently of one another, -O- or -N(R 3 )-, with R 3 denoting hydrogen or a linear or branched C1-C20 alkyl radical,
  • X and Y cannot simultaneously represent O or NR 3 ;
  • Ri and R 2 which are identical or different, denote a linear or branched C1-C10 alkyl radical, or a C5-C6 cycloalkyl radical, optionally substituted with one or more identical or different Ci-C 3 alkyl radicals
  • X and Y denote, independently of one another, -0- or -N(R 3 )-, with R 3 denoting hydrogen or a linear or branched d-do alkyl radical,
  • X and Y cannot simultaneously represent 0 or NR 3 ;
  • X or Y NR 3 , Ri and R 3 , or R 2 and R 3 , may form, with the nitrogen that bears them, a 5- to 6-membered heterocycle.
  • alkyl groups of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, fe/f-butyl, n-octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclohexyl or methylcyclohexyl groups.
  • a monoester-monoamide derivative of methylsuccinic acid of formula (I) is understood to encompass all mesomeric, tautomeric or optical isomeric forms.
  • compounds (a) to (j) below will more preferentially be used:
  • the derivatives of formula (I) in accordance with the invention are preferably present in the compositions of the invention in contents ranging from 1 % to 30% by weight and more preferentially from 3% to 20% by weight relative to the total weight of the composition.
  • Itaconic acid of formula (II) results, after dehydration, in itaconic anhydride of formula (III) which, after catalytic hydrogenation, makes it possible to obtain methylsuccinic anhydride of formula (IV).
  • Methylsuccinic anhydride (IV) is reacted with an amine of formula (V) (respectively an alcohol R2OH), to result in the monoamide-monoacid derivative (VI) (respectively monoester-monoacid derivative (VI)') which is then esterified with an alcohol of formula (V) in the presence of catalyst (respectively amidated with an amine HNR2R3) in order to give the derivative of formula (I).
  • Methylsuccinic anhydride of formula (IV), (CAS No. 4100-80-5) is readily available commerically, especially from Sigma-Aldrich or PCAS.
  • the compound (j) is novel and constitutes one subject of the invention.
  • compositions in accordance with the invention may also comprise other additional organic or inorganic UV-Screening agents which are active in the UV- A and/or UV-B regions that are water-soluble or liposoluble or else insoluble in the cosmetic solvents commonly used.
  • the additional UV-screening 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 additional organic UV-screening agents are chosen especially from anthranilic derivatives; cinnamic derivatives; salicylic derivatives; benzylidene camphor derivatives; benzophenone derivatives; ⁇ , ⁇ -diphenylacrylate derivatives; triazine derivatives; phenylbenzotriazole derivatives; benzalmalonate derivatives, especially those cited in patent US 5 624 663; phenylbenzimidazole derivatives; imidazoline derivatives; bis-benzoazolyl derivatives, as described in patents EP 669 323 and US 2 463 264; p-aminobenzoic acid (PABA) derivatives; methylenebis(hydroxyphenylbenzotriazole) derivatives as described in patent applications US 5 237 071 , US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 1 19; benzoxazole derivatives as described in patent applications EP 0 832 642, EP 1 027 883
  • organic UV-screening agents mention may be made of those denoted nereinbelow under their INCI name: para-Am inobenzoic acid derivatives: PABA,
  • Ethylhexyl dimethyl PABA sold in particular under the name Escalol 507 by ISP, Glyceryl PABA,
  • PEG-25 PABA sold under the name Uvinul P25 by BASF.
  • Ethylhexyl salicylate sold under the name Neo Heliopan OS by Symrise,
  • TEA salicylate sold under the name Neo Heliopan TS by Symrise.
  • Ethylhexyl methoxycinnamate sold especially under the trade name Parsol MCX by DSM Nutritional Products,
  • Neo Heliopan E 1000 Isoamyl methoxycinnamate sold under the trade name Neo Heliopan E 1000 by Symrise,
  • Benzophenone-6 sold under the trade name Helisorb 1 1 by Norquay,
  • Benzophenone-8 sold under the trade name Spectra-Sorb UV-24 by American Cyanamid,
  • Phenylbenzimidazole sulfonic acid sold in particular under the trade name Eusolex 232 by Merck,
  • Ethylhexyl triazone sold in particular under the trade name Uvinul T150 by BASF,
  • Neo Heliopan MA Menthyl anthranilate sold under the trade name Neo Heliopan MA by Symrise.
  • Polyorganosiloxane containing benzalmalonate functions for instance Polysilicone-15, sold under the trade name Parsol SLX by DSM. 4,4-Diarylbutadiene derivatives:
  • - R'i and R' 2 which are identical or different, represent H, a linear or branched C1-C22 alkyl radical or a C3-C8 cycloalkyl radical that is unsubstituted or substituted with C1-C4 alkyl radicals;
  • - R'i and R' 2 may form, together with the nitrogen, a ring containing the group -(CH 2 )m- which may be interrupted by one or more -0-, -S- or by -NH-;
  • radical R'i may form, with the carbon alpha to the nitrogen, a ring containing the group -(CH 2 ) m -, which is uninterrupted or interrupted by one or more -0-, -S- or by -NH-;
  • R' 3 represents a linear or branched C1-C22 alkyl radical or a C3-C8 cycloalkyl radical that is unsubstituted or substituted with C1-C4 alkyl radicals;
  • - m is an integer ranging from 3 to 7;
  • R'i, R' 2 or R' 3 is an alkyl diradical or else R'i and R' 2 form, together with 2 nitrogen atoms, a cyclic -(CH 2 ) m - divalent radical,
  • R'i and R' 2 are not simultaneously a hydrogen atom.
  • the compounds of formula (VIII) may be in the ⁇ , ⁇ -, ⁇ , ⁇ - or ⁇ , ⁇ - geometric isomeric forms.
  • the compounds of formula (VIII) that are particularly preferred are those for which the following conditions are satisfied:
  • R' 2 denote a linear or branched C1-C3 alkyl or a Cs-Ce cycloalkyl
  • R' 3 denotes a linear or branched d-Cs alkyl
  • - n is equal to 1 or 2.
  • the merocyanine derivatives of formula (VIII) can be prepared according to a method described in patents US 4 045 229 and US 4 195 999, according to the following scheme (pathway 1 ):
  • R'i , R' 2 and A radicals have the same meanings as in the formula (VIII).
  • hydrophilic or water-soluble merocyanine compounds in accordance with the invention are chosen from the group formed by: (1 ) those corresponding to one of the formulae (XIV) and (XV) below, and the salts thereof:
  • R"i and R" 2 which are identical or different, represent H; a linear or branched C1-C22 alkyi radical which may contain from 1 to 3 oxygen atoms; a C3-C8 cycloalkyi radical, which is unsubstituted or substituted with C1-C4 alkyi radicals; it being possible for said radicals R"i and R" 2 to contain an alkyi sulphonate radical in its acid or salified form or one or two hydroxyl radicals;
  • - R"i and R" 2 may form, together with the nitrogen, a ring containing the group -(CH 2 ) P -, which is uninterrupted or interrupted by one or more -0-, -S- or by -NH-, - R"i may form, with the carbon alpha to the nitrogen, a ring containing the group -(CH 2 ) P -, which is uninterrupted or interrupted by one or more -0-, -S- or by -NH-,
  • - R" 3 represents a carboxyl, -COOR” 5 , -CONHR" 5 , -COR” 5 , -CONR" 5 R"i , S0 2 R" 5 or -CN group,
  • - R" 4 represents a carboxyl, -COOR” 6 , -CONHR" 6 , -COR” 6 , -CONR" 6 R" 2 or S0 2 R" 6 group,
  • R" 5 and R" 6 which are identical or different, represent a linear or branched C-i- C 22 alkyi radical which may contain from 1 to 3 oxygen atoms; a C3-C8 cycloalkyi radical, which is unsubstituted or substituted with Ci-C 4 alkyi radicals; it being possible for said radicals R" 5 and R" 6 to contain an alkyi sulphonate radical in its acid or salified form or one or two hydroxyl radicals,
  • - Z represents the group -(CH 2 )r, which is uninterrupted or interrupted by -0-, -S- or by -NRV, and/or is unsubstituted or substituted with one or two C1-C6 alkyi radicals,
  • R" 7 is a C1-C5 alkyi radical that may contain an alkyi sulphonate radical in its acid or salified form or one or two hydroxyl radicals,
  • R"i and R" 2 are not simultaneously a hydrogen atom
  • diradical means a divalent radical such that the two units
  • linear or branched alkyl radicals examples include: methyl, ethyl, n-propyl, isopropyl, 1 -methylethyl, butyl, pentyl, hexyl, 2- ethylhexyl, octyl, 1 -methylheptyl.
  • C3-C8 cycloalkyl radicals mention may be made of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1 -methylcyclopropyl, 1 -ethylcyclopropyl, 1 - propylcyclopropyl, 1 -butylcyclopropyl, 1 -methyl-1 -butylcyclopropyl, 1 ,2- dimethylcyclopropyl, 1 -methyl-2-ethylcyclopropyl, cyclooctyl.
  • the acceptable salts of the merocyanine compounds described in the present invention comprise conventional non-toxic salts of said compounds, such as those formed from organic or mineral bases, such as amine salts, for instance salts of alkanolamines such as triethanolamine, amino acid salts or aminopropanediol salts, and salts of an alkali metal or alkaline-earth metal, for instance sodium or potassium.
  • amine salts for instance salts of alkanolamines such as triethanolamine, amino acid salts or aminopropanediol salts, and salts of an alkali metal or alkaline-earth metal, for instance sodium or potassium.
  • the preferred salts are salts of an alkali metal such as sodium or potassium, or salts of an amine such as triethanolamine.
  • R"i denotes hydrogen; a linear or branched d-Cs alkyl radical possibly containing from 1 to 3 oxygen atoms,
  • R" 2 denotes a linear or branched d-Cs alkyl possibly containing from 1 to 3 oxygen atoms or a C5-C6 cycloalkyl
  • R" 3 denotes a group -COOR" 5 , -CN or -CONHR" 5 ,
  • R" 4 denotes a group -COOR" 6 , -CONHR" 6 or -S0 2 R" 6 ,
  • R" 5 denotes a linear or branched Ci-Ci 2 alkyl possibly containing from 1 to 3 oxygen atoms,
  • o is equal to 1 or 2;
  • R"i denotes hydrogen; a linear or branched d-do alkyl possibly containing from 1 to 3 oxygen atoms,
  • R" 2 denotes a linear or branched d-do alkyl possibly containing from 1 to 3 oxygen atoms; a C5-C6 cycloalkyl,
  • R" 3 denotes a group -COOR" 5 or CN
  • R" 4 denotes a group -COOR" 6 or -S0 2 R" 6 ,
  • R" 5 denotes a linear or branched d-C-12 alkyl possibly containing from 1 to 3 oxygen atoms
  • Z is -(CH 2 )3- which is unsubstitituted or substituted with two CH 3 groups, o is equal to 1 or 2;
  • linear merocyanine derivatives in accordance with the invention in particular those of formula (XIV), may be prepared according to a method described in patents US 4045229, US 4195999 and US 2009/0170008 according to the following scheme (pathway 1 ):
  • cyclic merocyanine derivatives in accordance with the invention in particular those of formula (XV), may be prepared according to a method described in IP.COM Journal 9(5A), 29-30 (2009) according to the following scheme:
  • the preferential additional organic UV-screening agents are chosen from:
  • the additional inorganic screening agents are chosen from coated or uncoated metal oxide pigments, such as, for example, pigments formed of titanium oxide (amorphous or crystalline in the 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 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 amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (titanium or aluminium alkoxides), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
  • silicones are organosilicon polymers or oligomers of linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and are essentially constituted of a repetition of main units in which the silicon atoms are linked together via oxygen atoms (siloxane bond), optionally substituted hydrocarbon-based radicals being directly attached via a carbon atom to said silicon atoms.
  • silicones also includes the silanes required for their preparation, in particular alkylsilanes.
  • the silicones used for the coating of the pigments suitable for the present invention are preferably chosen from the group containing alkylsilanes, polydialkylsiloxanes and polyalkylhydrosiloxanes. More preferably still, the silicones are chosen from the group containing octyltrimethylsilane, poly- dimethylsiloxanes and polymethylhydrosiloxanes.
  • the metal oxide pigments may have been treated with other surface agents, in particular with cerium oxide, alumina, silica, aluminium compounds or silicon compounds, or mixtures thereof.
  • the coated pigments are more particularly titanium oxides that have been coated:
  • silica and alumina such as the products Microtitanium Dioxide MT 500 SA and Microtitanium Dioxide MT 100 SA from the company Tayca, Tioveil from the company Tioxide and Mirasun TiW 60 from the company Rhodia,
  • - with alumina such as the products Tipaque TTO-55 (B) and Tipaque TTO-55 (A) from the company Ishihara and UVT 14/4 from the company Kemira, - with alumina and aluminium stearate, such as the product Microtitanium Dioxide MT 100 TV, MT 100 TX, MT 100 Z and MT-01 from the company Tayca, and the products Solaveil CT-10 W, Solaveil CT 100 and Solaveil CT 200 from the company Uniqema,
  • titanium oxide pigments treated with a silicone are preferably T1O2 treated with octyltnmethylsilane, such as the product sold under the trade name T 805 by the company Degussa Silicas, T1O2 treated with a polydimethylsiloxane, such as the product sold under the trade name 70250 Cardre UF TiO2SI3 by the company Cardre, anatase/rutile T1O2 treated with a polydimethylhydrosiloxane, such as the product sold under the trade name Microtitanium Dioxide USP Grade Hydrophobic by the company Color Techniques.
  • T1O2 treated with octyltnmethylsilane such as the product sold under the trade name T 805 by the company Degussa Silicas
  • T1O2 treated with a polydimethylsiloxane such as the product sold under the trade name 70250 Cardre UF TiO2SI3 by the company Cardre
  • the uncoated titanium oxide pigments are sold, for example, by the company Tayca under the trade names Microtitanium Dioxide MT 500 B or Microtitanium Dioxide MT 600 B, by the company Degussa under the name P 25, by the company Sensient - LCW under the name Transparent titanium oxide 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 pigments are, for example:
  • coated zinc oxide pigments are, for example: - those sold under the name Z-Cote HP1 by the company Sunsmart (dimethicone-coated ZnO);
  • Zinc Oxide CS-5 those sold under the name Zinc Oxide CS-5 by the company Toshibi (ZnO coated with polymethylhydrosiloxane);
  • Nanogard Zinc Oxide FN those sold under the name Nanogard Zinc Oxide FN by the company Nanophase Technologies (as a 40% dispersion in Finsolv TN, C12-C15 alkyl benzoate);
  • Daitopersion ZN-30 and Daitopersion ZN-50 by the company Daito (dispersions in cyclopolymethylsiloxane/oxyethylenated poly- dimethylsiloxane, containing 30% or 50% of nanozinc oxides coated with silica and polymethylhydrosiloxane);
  • Nanox Gel TN those sold under the name Nanox Gel TN by the company Elementis (ZnO dispersed at a concentration of 55% in C12-C15 alkyl benzoate with hydroxystearic acid polycondensate).
  • the uncoated cerium oxide pigments are sold, for example, under the name Colloidal Cerium Oxide by the company Rhone-Poulenc.
  • the uncoated iron oxide pigments are sold, for example, by the company Arnaud under the names Nanogard WCD 2002 (FE 45B), Nanogard Iron FE 45 BL AQ, Nanogard FE 45R AQ and Nanogard WCD 2006 (FE 45R) or by the company Mitsubishi under the name TY-220.
  • the coated iron oxide pigments are sold, for example, 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 Transparent Iron Oxide.
  • inorganic screening agent that may be incoporated into the compositions of the invention, mention may also be made of mixtures of metal oxides, especially of titanium dioxide and of cerium dioxide, including the equal-weight mixture of titanium dioxide and of cerium dioxide coated with silica, sold by the company Ikeda under the name Sunveil A, and also the mixture of titanium dioxide and of zinc dioxide coated with alumina, silica and silicone, such as the product M 261 sold by the company Kemira, or the mixture of titanium dioxide and of zinc dioxide coated with alumina, silica and glycerol, such as the product M 21 1 sold by the company Kemira.
  • mixtures of metal oxides especially of titanium dioxide and of cerium dioxide, including the equal-weight mixture of titanium dioxide and of cerium dioxide coated with silica, sold by the company Ikeda under the name Sunveil A, and also the mixture of titanium dioxide and of zinc dioxide coated with alumina, silica and silicone, such as the product M 261 sold by the company Kemira, or the mixture of titanium dioxide
  • compositions in accordance with the present invention may also comprise standard cosmetic adjuvants chosen especially from fatty substances such as oils, organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic, zwitterionic or amphoteric emulsifying surfactants, active agents, fillers, polymers, propellants, acidifying or basifying agents or any other ingredient usually used in cosmetics and/or dermatology.
  • standard cosmetic adjuvants chosen especially from fatty substances such as oils, organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic
  • Oils that may be mentioned include mineral oils (liquid paraffin); plant oils (sweet almond oil, macadamia oil, grapeseed oil or jojoba oil); synthetic oils, for instance perhydrosqualene, fatty alcohols, fatty amides (for instance isopropyl lauroyl sarcosinate sold under the name Eldew SL-205 by the company Ajinomoto), fatty acids or fatty esters, for instance the C12-C15 alkyl benzoate sold under the trade name Finsolv TN or Witconol TN by the company Witco, 2- ethylphenyl benzoate, for instance the commercial product sold under the name X-Tend 226® by the company ISP, octyl palmitate, isopropyl lanolate and triglycerides, including capric/caprylic acid triglycerides, dicaprylyl carbonate sold under the name Cetiol CC by the company Cognis, oxyethyl
  • Waxy compounds that may be mentioned include carnauba wax, beeswax, hydrogenated castor oil, polyethylene waxes and polymethylene waxes, for instance the product sold under the name Cirebelle 303 by the company Sasol.
  • organic solvents that may be mentioned are lower alcohols and polyols.
  • the latter can be chosen from glycols and glycol ethers, such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.
  • Hydrophilic thickeners that may be mentioned include carboxyvinyl polymers, such as Carbopols (Carbomers) and the Pemulens (acrylates/C10-C30 alkyl acrylate copolymer); polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide/C13-14 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyltaurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; 2-acrylamido-2-methylpropanesulphonic acid polymers and copolymers, optionally crosslinked and/or neutralized, for instance poly(2- acrylamido-2-methylpropanesulphonic acid) sold by the company Hoechst under the trade name Hostacerin AMPS (CTFA name: ammonium polyacryloyldimethyl taurate or Simulgel 800 sold by the
  • Lipophilic thickeners that may be mentioned include synthetic polymers, such as the poly(C10-C30 alkyl acrylates) sold under the names Intelimer IPA 13-1 and Intelimer IPA 13-6 by the company Landec, or else modified clays, such as hectorite and its derivatives, for instance the products sold under the name Bentone.
  • synthetic polymers such as the poly(C10-C30 alkyl acrylates) sold under the names Intelimer IPA 13-1 and Intelimer IPA 13-6 by the company Landec, or else modified clays, such as hectorite and its derivatives, for instance the products sold under the name Bentone.
  • compositions according to the invention may be prepared according to the techniques that are well known to those skilled in the art. They may in particular be in the form of a simple or complex emulsion (O/W, W/O, O/W/O or W/O/W) such as a cream, a milk or a cream-gel; in the form of an aqueous gel; in the form of a lotion. 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 are preferably in the form of an oil- in-water or water-in-oil emulsion.
  • the emulsification processes that may be used are of the paddle or impeller, rotor-stator or HHP type.
  • the emulsions generally contain at least one emulsifying surfactant chosen from amphoteric, anionic, cationic and nonionic emulsifying surfactants, which are used alone or as a mixture.
  • the emulsifiers are appropriately chosen according to the emulsion to be obtained (W/O or O/W).
  • emulsifying surfactants that may be used for the preparation of the W/O emulsions
  • examples that may be mentioned include sorbitan, glycerol or sugar alkyl esters or ethers; 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 alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning; cetyldimethicone copolyol, such as the product sold under the name Abil EM 90R by the company Goldschmidt, and the mixture of cetyldimethicone copolyol, of polyglyceryl isostearate (4 mol) and of hexyl laurate, sold under the name Abil WE O9 by the company Goldsch
  • coemulsifiers may also be added thereto, which may be chosen advantageously from the group comprising polyol alkyl esters.
  • Polyol alkyl esters that may especially be mentioned include polyethylene glycol esters, for instance PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135 by the company ICI.
  • Glycerol and/or sorbitan esters that may be mentioned include, for example, polyglyceryl isostearate, such as the product sold under the name Isolan Gl 34 by the company Goldschmidt, sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI, sorbitan glyceryl isostearate, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof.
  • examples of emulsifying surfactants include nonionic emulsifying surfactants such as oxyalkylenated (more particularly polyoxyethylenated) esters of fatty acids and of glycerol; oxyalkylenated esters of fatty acids and of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) esters of fatty acids, such as the PEG 100 stearate/glyceryl stearate mixture sold, for example, by ICI under the name Arlacel 165; oxyalkylenated (oxyethylenated and/or oxypropylenated) ethers of fatty alcohols; esters of sugars, such as sucrose stearate; or ethers of fatty alcohol and of sugar, in particular alkyl polyglucosides (APGs), such as decyl glucoside and lauryl glu
  • APGs alkyl polyglucosides
  • the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol can be in the form of a self- emulsifying composition, for example as described in document WO-A- 92/06778.
  • the aqueous phase of this emulsion may comprise a nonionic vesicular dispersion prepared according to known processes (Bangham, Standish and Watkins, J. Mol. 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, especially cosmetic treatments, of the skin, lips, nails, eyelashes, eyebrows and hair, including the scalp, especially for protecting and/or caring for the skin, lips and/or hair, and/or for making up the skin and/or lips and/or eyelashes and/or eyebrows and/or nails.
  • Another subject of the present invention is constituted of the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and/or scalp, especially care products, sun protection products and makeup products.
  • the cosmetic compositions according to the invention may be used, for example, as makeup products.
  • compositions according to the invention may be used, for example, as care products and/or sun protection products for the face and/or the body.
  • These compositions according to the invention may be of liquid to semi- liquid consistency, such as milks, relatively smooth 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 vaporizable 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 comprise non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and also aerosol pumps using compressed air as propellant. These devices are described in patents US 4 077 441 and US 4 850 517 (which form 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, hydrofluorinated 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.
  • propellants such as, for example, hydrofluorinated compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane.
  • compositions according to the invention may also comprise additional cosmetic and dermatological active agents. Mention may be made, among active agents, of:
  • moisturizers for instance polyols such as glycerol, butylene glycol or propylene glycol;
  • a person skilled in the art will preferably select at least one active agent chosen from desquamating agents, sebum-regulating agents or anti-seborrhoeic agents, and astringents.
  • compositions of the invention may be advantageous to incorporate into the compositions of the invention other additional ingredients.
  • these additional ingredients may impart an immediate visual effect that will be relayed by the biological effect of the aforementioned active agents. They may also, via a mechanical action (e.g.:abrasive fillers), amplify the effect of the aforementioned biological active agents.
  • a mechanical action e.g.:abrasive fillers
  • composition according to the invention may also comprise at least one agent chosen from matting agents, fillers with a soft-focus effect, agents for promoting the naturally pinkish coloration of the skin, abrasive fillers or exfoliants, and mixtures thereof.
  • matting agent means agents intended to make the skin visibly more matt and less shiny.
  • the matting effect of the agent and/or composition containing it may especially be evaluated using a gonioreflectometer, by measuring the ratio R between the specular reflection and the scattered reflection.
  • a value of R of less than or equal to 2 generally indicates a matting effect.
  • the matting agent may especially be chosen from a rice starch or a corn starch: INCI name: Zea mays (Corn) Starch, kaolinite, talc, a pumpkin seed extract, cellulose microbeads, plant fibres, synthetic fibres, in particular polyamide fibres, expanded acrylic copolymer microspheres, fillers with an optical effect, polyamide powders, silica powders, polytetrafluoroethylene powders, silicone resin powders, acrylic polymer powders, wax powders, polyethylene powders, powders of elastomeric crosslinked organopolysiloxane coated with silicone resin, talc/titanium dioxide/alumina/silica composite powders, compounds that absorb and/or adsorb sebum, and mixtures thereof.
  • INCI name Zea mays (Corn) Starch
  • kaolinite kaolinite
  • talc a pumpkin seed extract
  • cellulose microbeads plant fibres
  • synthetic fibres in particular polyamide fibres,
  • matting agents examples include:
  • a rice or corn starch such as the product sold under the trade name Farmal CS 3650 Plus 036500 by National Starch or in particular an aluminium starch octenyl succinate sold under the name Dry Flo® by the company National Starch;
  • - natural or synthetic fibres such as silk fibre, cotton fibre, wool fibre, flax fibre, cellulose fibre extracted especially from wood, from vegetables or from algae, polyamide (Nylon®) fibre, modified cellulose fibre, poly-p- phenyleneterephthamide fibre, acrylic fibre, polyolefin fibre, glass fibre, silica fibre, aramid fibre, carbon fibre, Teflon® fibre, insoluble collagen fibre, polyester fibre, polyvinyl chloride or polyvinylidene chloride fibre, polyvinyl alcohol fibre, polyacrylonitrile fibre, chitosan fibre, polyurethane fibre, polyethylene phthalate fibre, fibres formed from a mixture of polymers, resorbable synthetic fibres, and mixtures thereof described in patent application EP 1 151 742;
  • nylon® powders for instance Nylon 12 particles of the Orgasol type from Arkema, with a mean size of 10 microns and a refractive index of 1 .54,
  • silica powders for instance Silica beads SB150 from Miyoshi with a mean size of 5 microns and a refractive index of 1 .45,
  • polytetrafluoroethylene powders for instance PTFE Ceridust 9205F from Clariant, with a mean size of 8 microns and a refractive index of 1 .36,
  • silicone resin powders for instance the silicone resin Tospearl 145A from GE Silicone with a mean size of 4.5 microns and a refractive index of 1 .41 ,
  • acrylic polymer powders especially of polymethyl (meth)acrylate, for instance the PMMA particles Jurymer MBI from Nihon Junyoki, with a mean size of
  • - wax powders for instance the paraffin wax particles Microease 1 14S from Micropowders, with a mean size of 7 microns and a refractive index of 1 .54
  • polyethylene powders especially comprising at least one ethylene/acrylic acid copolymer, and in particular constituted of ethylene/acrylic acid copolymers, for instance the particles Flobeads EA 209 from Sumitomo (with a mean size of 10 microns and a refractive index of 1 .48),
  • silica powders for instance the porous silica microspheres sold under the name Silica Beads SB-700 sold by the company Miyoshi, the products Sunsphere® H51 , Sunsphere® H33 and Sunsphere® H53 sold by the company Asahi Glass; the polydimethylsiloxane-coated amorphous silica microspheres sold under the name SA Sunsphere® H- 33 and SA Sunsphere® H-53 sold by the company Asahi Glass;
  • nylon® polyamide (Nylon®) powders, for instance Orgasol® 4000 sold by the company Arkema;
  • Microsponge® Skin Oil Adsorber sold by the company Dow Corning, or Ganzpearl® GMP-0820 sold by the company Ganz Chemical; of polyallyl methacrylate/ethylene glycol dimethacrylate, for instance Poly-Pore® L200 or Poly-Pore® E200 sold by the company Amcol; of ethylene glycol dimethacrylate/lauryl methacrylate copolymer, for instance Polytrap® 6603 sold by the company Dow Corning;
  • - silicate particles such as alumina silicate
  • magnesium aluminium silicate particles such as saponite or magnesium aluminium silicate hydrated with a sodium sulphate sold under the trade name Sumecton® by the company Kunimine;
  • Preferred matting agents that may be used according to the invention include a pumpkin seed extract, a rice or corn starch, kaolinite, silicas, talc, polyamide powders, polyethylene powders, acrylic copolymer powders, expanded acrylic copolymer microspheres, silicone resin microbeads and mixed silicate particles, and mixtures thereof.
  • Fillers with a soft-focus effect may be any material capable of modifying and hiding wrinkles by virtue of its intrinsic physical properties. These fillers may especially modify wrinkles via a tensioning effect, a covering effect or a soft-focus effect.
  • the following compounds may be given as examples: - porous silica microparticles, for instance the Silica Beads® SB150 and SB700 from Miyoshi with a mean size of 5 pm; the series H Sunspheres® from Asahi Glass, for instance Sunspheres H33, H51 with respective sizes of 3.5 and 5 pm;
  • NLK 500®, NLK 506® and NLK 510® from Takemoto Oil and Fat, especially described in EP-A-1 579 849;
  • silicone resin powders for instance the silicone resin Tospearl® 145A from GE Silicone, with a mean size of 4.5 pm;
  • acrylic polymers especially of polymethyl (meth)acrylate, for instance the PMMA particles Jurimer MBI® from Ninon Junyoki, with a mean size of 8 pm, the hollow PMMA spheres sold under the name Covabead® LH85 by the company Wackherr, and vinylidene/acrylonitrile/methylene methacrylate expanded microspheres sold under the name Expancel®;
  • MicroPowders with a mean size of 7 pm;
  • polyethylene powders especially comprising at least one ethylene/acrylic acid copolymer, for instance the Flobeads® EA 209 E particles from Sumitomo, with a mean size of 10 pm;
  • talc/titanium dioxide/alumina/silica composite powders for instance those sold under the name Coverleaf AR-80® by the company Catalyst & Chemicals;
  • abrasive fillers which, via a mechanical effect, smooth out the skin microrelief, such as abrasive silica, for instance Abrasif SP® from Semanez or nut or shell powders (for example of apricot or walnut, from Cosmetochem).
  • abrasive silica for instance Abrasif SP® from Semanez or nut or shell powders (for example of apricot or walnut, from Cosmetochem).
  • the fillers with an effect on the signs of ageing are especially chosen from porous silica microparticles, hollow hemispherical silicone particles, silicone resin powders, acrylic copolymer powders, polyethylene powders, crosslinked elastomeric organopolysiloxane powders coated with silicone resin, talc/titanium dioxide/alumina/silica composite powders, precipitated calcium carbonate, magnesium hydrogen carbonate, barium sulphate, hydroxyapatite, calcium silicate, cerium dioxide, glass or ceramic microcapsules, and silk fibres or cotton fibres, and mixtures thereof.
  • the filler may be a soft-focus filler.
  • soft-focus filler means a filler which in addition gives the complexion transparency and a hazy effect.
  • the soft-focus fillers have a mean particle size of less than or equal to 15 microns. These particles may be in any form and in particular may be spherical or non-spherical. These fillers are more preferably non-spherical.
  • the soft-focus fillers may be chosen from silica and silicate powders, especially alumina powder, powders of polymethyl methacrylate (PMMA) type, talc, silica/Ti02 or silica/zinc oxide composites, polyethylene powders, starch powders, polyamide powders, styrene/acrylic copolymer powders and silicone elastomers, and mixtures thereof.
  • silica and silicate powders especially alumina powder, powders of polymethyl methacrylate (PMMA) type, talc, silica/Ti02 or silica/zinc oxide composites, polyethylene powders, starch powders, polyamide powders, styrene/acrylic copolymer powders and silicone elastomers, and mixtures thereof.
  • talc with a number-average size of less than or equal to 3 microns for example talc with a number-average size of 1 .8 microns and especially the product sold under the trade name Talc P3® by the company Nippon Talc, Nylon® 12 powder, especially the product sold under the name Orgasol 2002 Extra D Nat Cos® by the company Atochem, silica particles 1 % to 2% surface-treated with a mineral wax (INCI name: hydrated silica (and) paraffin) such as the products sold by the company Degussa, amorphous silica microspheres, such as the products sold under the name Sunsphere, for example of reference H-53® by the company Asahi Glass, and silica microbeads such as those sold under the name SB-700® or SB-150® by the company Miyoshi, this list not being limiting.
  • a mineral wax INCI name: hydrated silica (and) paraffin
  • amorphous silica microspheres such
  • the concentration of these fillers with an effect on the signs of ageing in the compositions according to the invention may be between 0.1 % and 40%, or even between 0.1 % and 20% by weight, relative to the total weight of the composition.
  • a self-tanning agent i.e. an agent which, when applied to the skin, especially to the face, can produce a tan effect that is more or less similar in appearance to that which may result from prolonged exposure to the sun (natural tan) or under a UV lamp;
  • an additional colouring agent i.e. any compound that has particular affinity for the skin, which allows it to give the skin a lasting, non-covering coloration (i.e. that does not have a tendency to opacify the skin) and that is not removed either with water or using a solvent, and that withstands both rubbing and washing with a solution containing surfactants.
  • a lasting coloration is thus distinguished from the superficial and transient coloration provided, for example, by a makeup pigment;
  • self-tanning agents examples include:
  • DHA dihydroxyacetone
  • alkali metal and/or alkaline-earth metal hydrogen carbonates are examples of alkali metal and/or alkaline-earth metal hydrogen carbonates.
  • the self-tanning agents are generally chosen from monocarbonyl or polycarbonyl compounds, for instance isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose, pyrazolin-4,5-dione derivatives as described in patent application FR 2 466 492 and WO 97/35842, dihydroxyacetone (DHA) and 4,4-dihydroxypyrazolin-5-one derivatives as described in patent application EP 903 342.
  • DHA will preferably be used.
  • DHA can be used in free and/or encapsulated form, for example encapsulated in lipid vesicules, such as liposomes, described in particular in patent application WO 97/25970.
  • the self-tanning agent is present in an amount ranging from 0.01 % to 20% by weight and preferably in an amount of between 0.1 % and 10% of the total weight of the composition.
  • These dyes may be chosen from synthetic or natural direct dyes.
  • dyes may be chosen, for example, from red or orange dyes of the fluorane type such as those described in patent application FR 2 840 806. Mention may be made, for example, of the following dyes:
  • dyes may also be chosen from anthraquinones, caramel, carmine, carbon black, azulene blues, methoxalene, trioxalene, guajazulene, chamuzulene, rose Bengal, eosin 10B, cyanosine and daphnin.
  • dyes may also be chosen from indole derivatives, for instance the monohydroxyindoles as described in patent FR 2 651 126 (i.e.: 4-, 5-, 6- or 7- hydroxyindole) or the dihydroxyindoles as described in patent EP-B-0 425 324 (i.e.: 5,6-dihydroxyindole, 2-methyl-5,6-dihydroxyindole, 3-methyl-5,6- dihydroxyindole or 2,3-dimethyl-5,6-dihydroxyindole).
  • indole derivatives for instance the monohydroxyindoles as described in patent FR 2 651 126 (i.e.: 4-, 5-, 6- or 7- hydroxyindole) or the dihydroxyindoles as described in patent EP-B-0 425 324 (i.e.: 5,6-dihydroxyindole, 2-methyl-5,6-dihydroxyindole, 3-methyl-5,6- dihydroxyindole or 2,3
  • exfoliants that may be used in compositions according to the invention, examples that may be mentioned include exfoliant or scrubbing particles of mineral, plant or organic origin.
  • exfoliant or scrubbing particles of mineral, plant or organic origin use may be made, for example, of polyethylene beads or powder, Nylon powder, polyvinyl chloride powder, pumice powder, ground apricot kernels or walnut shells, sawdust, glass beads and alumina, and mixtures thereof.
  • Mention may also be made of Exfogreen® from Solabia (bamboo extract), extracts of strawberry achenes (Strawberry Achenes from Greentech), peach kernel powder, apricot kernel powder, and finally, in the field of plant powders with an abrasive effect, mention may be made of cranberry kernel powder.
  • peach kernel powder As abrasive fillers or exfoliants that are preferred according to the invention, mention will be made of peach kernel powder, apricot kernel powder, cranberry kernel powder, strawberry achene extracts and bamboo extracts.
  • methylsuccininic anhydride (9.23 g, 0.081 mol) is dissolved in 50 ml of THF. It is cooled in an iced water bath and n-butylamine (8 ml, 0.081 mol) is poured in rapidly. When the exothermic reaction has finished, the reaction mixture is left at room temperature for 12 hours. The reaction mixture is stripped of its solvent by vacuum evaporation. Thus, 15 g (quantitative yield) of 4- (butylamino)-2-methyl-4-oxobutanoic acid are obtained in the form of a pale yellow oil and are used in the following step.
  • the remaining percentage of dibenzoylmethane derivative after exposure to a solar simulator of a formula spread as films about 20 pm thick is measured.
  • the evaluation is performed by HPLC analysis of the screening agent in solution, after extraction of the films, by comparing the irradiated and non-irradiated samples.
  • Solar simulator Oriel 1000 W machine equipped with a 4-inch output, with a 81017 filter and a dichroic mirror. The samples are exposed in the horizontal position.
  • UV-meter Osram Centra machine equipped with two reading heads, one for UV- A, the other for UV-B.
  • the simulator/UV-meter assembly is calibrated annually by spectroradiometry. Irradiance measurements taken at the start and end of exposure by placing the reading heads at the position of the sample.
  • the irradiances are:
  • the monoester-monoamide compounds of 2-methylsuccinic acid are introduced into the common support defined above at a concentration of 4% by weight in the presence of 1 % by weight of butyl methoxy dibenzoylmethane of composition:
  • each support disc is introduced into a 600 ml jar with 10 ml of a suitable solvent (in general, EtOH); the assembly is placed in an ultrasonic tank for 5 minutes.
  • a suitable solvent in general, EtOH
  • the solution is then transferred into bottles suitable for the support that is compatible with the HPLC analysis machine used.
  • the analytical conditions may be adjusted as a function of the active agent tested.
  • the percentage remaining is calculated from averages obtained from the irradiated and non-irradiated samples, as described below:
  • the monoester-monoamide derivative of 2-methylsuccinic acid of formula (j) of Example 1 according to the invention has a photostabilizing effect with respect to the dibenzoylmethane derivative that is substantially greater than that obtained with comparative compound 2 from the prior art and a photostabilizing effect equivalent to that of comparative compound 1 from the prior art; in the latter case, the emulsion is stable over time for the compound (j) of the invention whereas the emulsion breaks in the case of comparative compound 1 .
  • the aqueous phase (Phase B) comprising all of its ingredients is heated to 80°C in a water bath.
  • the fatty phase (Phase A) comprising all of its ingredients is heated to 80°C in a water bath.
  • A is emulsified in B with stirring of rotor-stator type (device from Moritz).
  • Phase C is incorporated and the mixture is allowed to return to ambient temperature with moderate stirring.
  • the triethanolamine is introduced so as to adjust the pH to the value desired at the end of manufacture.
  • the anti-sun emulsions obtained are stable during storage and do not have crystals or precipitates.

Abstract

La présente invention concerne une composition cosmétique contenant la combinaison d'au moins un agent de criblage du type dérivé de dibenzoylméthane et d'au moins un composé monoester-monoamide de l'acide méthylsuccinique répondant à la formule (I) ci-dessous ou un isomère géométrique de celui-ci : L'invention concerne en outre un procédé de photostabilisation par rayonnement d'au moins un agent de criblage du type dérivé de dibenzoylméthane avec un composé monoester-monoamide de l'acide méthylsuccinique répondant à la formule (I) telle que définie ci-dessus.
PCT/EP2012/053066 2011-03-09 2012-02-23 Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé monoester-monoamide d'acide méthylsuccinique; procédé de photostabilisation d'un dérivé de dibenzoylméthane WO2012119860A1 (fr)

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FR1151918A FR2972348B1 (fr) 2011-03-09 2011-03-09 Composition cosmetique contenant un derive de dibenzoylmethane et un compose monoester monoamide d'acide methyl succinique ; procede de photostabilisation
FR1151918 2011-03-09
US201161451842P 2011-03-11 2011-03-11
US61/451,842 2011-03-11

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015145464A3 (fr) * 2014-03-27 2016-04-21 Kancor Ingredients Ltd Composition d'écran solaire photostable pour application topique
CN117243834A (zh) * 2023-10-09 2023-12-19 广州百孚润化工有限公司 高含量辛酰甘氨酸控油祛痘组合物及其制备方法及应用
CN117243834B (zh) * 2023-10-09 2024-04-26 广州百孚润化工有限公司 高含量辛酰甘氨酸控油祛痘组合物及其制备方法及应用

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WO2015145464A3 (fr) * 2014-03-27 2016-04-21 Kancor Ingredients Ltd Composition d'écran solaire photostable pour application topique
US20170065510A1 (en) * 2014-03-27 2017-03-09 Kancor Ingredients Ltd Photostable sunscreen composition for topical application
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CN117243834A (zh) * 2023-10-09 2023-12-19 广州百孚润化工有限公司 高含量辛酰甘氨酸控油祛痘组合物及其制备方法及应用
CN117243834B (zh) * 2023-10-09 2024-04-26 广州百孚润化工有限公司 高含量辛酰甘氨酸控油祛痘组合物及其制备方法及应用

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