WO2023110777A1 - Composition cosmétique ou dermatologique comprenant une mérocyanine et du pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate - Google Patents

Composition cosmétique ou dermatologique comprenant une mérocyanine et du pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate Download PDF

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WO2023110777A1
WO2023110777A1 PCT/EP2022/085446 EP2022085446W WO2023110777A1 WO 2023110777 A1 WO2023110777 A1 WO 2023110777A1 EP 2022085446 W EP2022085446 W EP 2022085446W WO 2023110777 A1 WO2023110777 A1 WO 2023110777A1
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weight
composition according
formula
butyl
preferentially
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PCT/EP2022/085446
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English (en)
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Flavie GILLANT
Cécile Boschet
Stéphane DOUEZAN
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L'oreal
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Publication of WO2023110777A1 publication Critical patent/WO2023110777A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • 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
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • composition comprising a merocyanine and pentaery th rity I tetra-di-t-butyl hydroxyhydrocinnamate
  • the present invention relates to a cosmetic or dermatological composition
  • a cosmetic or dermatological composition comprising at least one merocyanine of formula (3) that will be defined below in detail and pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate.
  • the present invention also relates to a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of said keratin material, of at least one composition according to the invention as defined above.
  • the invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
  • the invention also relates to a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
  • UVA rays with wavelengths of between 320 and 400 nm penetrate more deeply into the skin than UVB rays. UVA rays cause immediate and persistent browning of the skin. Daily exposure to UVA rays, even of short duration, under normal conditions can result in damage to the collagen fibres and the elastin, which is reflected by a modification of the microrelief of the skin, the appearance of wrinkles and uneven pigmentation (liver spots, heterogeneity of the complexion).
  • UVA and/or UVB radiation generally contain organic UV-screening agents and/or inorganic UV-screening agents, which function according to their own chemical nature and according to their own properties by absorption, reflection or scattering of the UV radiation. They generally contain mixtures of liposoluble organic screening agents and/or of water-soluble UV-screening agents combined with metal oxide pigments such as titanium dioxide or zinc oxide.
  • compositions intended to limit darkening of the skin, and to improve the colour and uniformity of the complexion have been proposed to date. It is well known in the field of antisun products that such compositions can be obtained by using UV-screening agents, and in particular UVB-screening agents. Some compositions may also contain UVA-screening agents. This screening system must cover UVB protection for the purpose of limiting and controlling the neosynthesis of melanin promoting overall pigmentation, but must also cover UVA protection in order to limit and control the oxidation of the already existing melanin resulting in darkening of the skin colour.
  • composition containing a particular combination of UV-screening agents that would be specially suitable for photoprotection of the skin and particularly for an improvement in the quality of the skin both in terms of the colour and in terms of its mechanical elasticity properties.
  • this improvement is particularly desired on skin that is already pigmented, for the purpose of not increasing either the pigmentary melanin load or the structure of the melanin already present within the skin.
  • the majority of organic UV-screening agents consist of aromatic compounds which absorb in the wavelength range between 280 and 370 nm.
  • the desired photoprotective compounds must also have good cosmetic properties, good solubility in the usual solvents and in particular in fatty substances such as oils, or in water, and also good photostability alone or in combination with other UV-screening agents. They must also be colourless or at least have a colour that is cosmetically acceptable for consumers.
  • a cosmetic or dermatological composition comprising at least one merocyanine of formula (3) that will be defined below in detail and pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate.
  • organic screening agents such as dibenzoylmethane derivatives, for example.
  • additional screening agents in particular dibenzoylmethane derivatives, can destabilize compositions comprising a merocyanine.
  • Dibenzoylmethane derivatives and in particular 4-tert-butyl-4'- methoxydibenzoylmethane, constitute a family of particularly effective IIV-A screening agents having a high intrinsic absorption power.
  • These dibenzoylmethane derivatives which are now products well known per se as UV-A-active screening agents, are described in particular in the French patent applications FR-A-2326405 and FR-A- 2440933, and also in European patent application EP-A-0114607; 4-tert-butyl-4'- methoxydibenzoylmethane is in addition currently sold under the trade name "PARSOL 1789 ®" by DSM Nutritional Products.
  • the present invention also relates to a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of said keratin material, of at least one composition according to the invention as defined above.
  • the invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
  • the invention also relates to a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
  • the present invention also relates to the use of pentaerythrityl tetra-d i-t- butyl hydroxyhydrocinnamate for photostabilizing a merocyanine of formula (3) as defined below, alone or in the presence of an additional screening agent, in particular in the presence of one or more dibenzoylmethane derivatives such as 4-tert-butyl-4'- methoxydibenzoylmethane.
  • composition according to the invention is intended for topical application and thus contains a physiologically acceptable medium.
  • physiologically acceptable medium means here a medium that is compatible with keratin materials.
  • the term “keratin material” notably means the skin, the scalp, keratin fibres such as the eyelashes, the eyebrows, head hair, bodily hair, the nails, and mucous membranes such as the lips, and more particularly the skin and the mucous membranes (of the body, face, area around the eyes, eyelids, lips, preferably of the body, face and lips).
  • the term "preventing” or “prevention” is intended to mean reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of ageing of a keratin material.
  • A is -O- or -NH;
  • R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more O.
  • the merocyanine compounds of the invention may be in the E/E- or E/Z geometric isomer forms thereof:
  • A is -O-;
  • R is a C1-C22 alkyl, which may be interrupted with one or more O.
  • the E/Z form has the following structure:
  • the E/E form has the following structure:
  • the screening merocyanines in accordance with the invention may be present in the compositions according to the invention in a concentration ranging from 0.1 % to 15% by weight, and preferentially from 0.2% to 10% by weight and even better still from 0.5% to 5% by weight relative to the total weight of the composition.
  • the compounds of formula (3) which form a carbocyclic ring containing 6 carbon atoms, may be prepared according to the protocols described in patent application WO 2007/071582, in IP.com Journal (2009), 9(5A), 29-30 IPCOM000182396D under the title “Process for producing 3-amino-2-cyclohexan-1 - ylidene compounds” and in US-A-4,749,643 on col. 13, line 66 - col. 14, line 57 and the references cited in this regard.
  • the compounds of formula (3) such as the compound 2- ethoxyethyl (2Z)-cyano ⁇ 3-[(3-methoxypropyl)am ino]cyclohex-2-en-1 - ylidenejethanoate (25), may be synthesized according to the synthesis scheme described in the publication from B. Winkler et al., Tetrahedron Letters, 55 (2014) 1749-1751 , entitled "A cyclic merocyanine IIV-A absorber: mechanism of formation and crystal structure" and represented below, for the compounds of formula (3): [formula 4]
  • composition according to the invention comprises pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate.
  • Pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate is a compound that belongs to the family of cinnamic acids and derivatives thereof, having the CAS number 6683-19-8.
  • a composition according to the invention comprises from 0.01 % to 2.5% by weight, preferably from 0.05% to 1 .5% by weight, more preferentially from 0.1 % to 0.3% by weight, of pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, relative to the total weight of the composition.
  • composition according to the present invention further comprises one or more derivatives of dibenzoylmethane chosen from those of the following formula, and/or mixtures thereof:
  • Ri, R4, RS and Re represent, independently of one another, a hydrogen atom; a hydroxy radical; a linear or branched C1-C4 alkyl radical; or a linear or branched C1-C4 alkoxy radical; and
  • R2 and R3 represent, independently of one another, a hydrogen atom; a hydroxy radical; a linear or branched C1-C4 alkyl radical; a linear or branched C1-C4 alkoxy radical; or form, with the 2 carbon atoms of the covalent C-R2 and C-R3 bonds, a 5- or 6-membered heterocycle which is optionally substituted by a linear or branched C1-C4 hydrocarbon chain.
  • R2 and R3 form a heterocycle with the 2 carbon atoms of the covalent C-R2 and C-R3 bonds, they preferably form a 5-membered aromatic heterocycle, more preferentially a furan ring.
  • R2 and R3 represent, independently of one another, a hydrogen atom; a hydroxy radical; a linear or branched C1-C4 alkyl radical; or a linear or branched C1-C4 alkoxy radical.
  • the compound(s) derived from dibenzoylmethane are chosen, alone or as a mixture, from 2- methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5- dimethyldibenzoylmethane, 4,4'-diisopropyldibenzoylmethane, 4,4'- dimethoxydibenzoylmethane, 4-tert-butyl-4'-methoxydibenzoylmethane, 2-methyl-5- isopropyl-4'-methoxydibenzoylmethane, 2-methyl-5-tert-butyl-4'- methoxydibenzoylmethane, 2,4-dimethyl-4'-methoxy
  • 4-isopropyldibenzoylmethane is sold under the name "Eusolex 9020" by Merck, and 4-tert-butyl-4'-methoxydibenzoylmethane or Butyl Methoxydibenzoylmethane, of formula: [formula 7]
  • composition according to the invention comprises 4-tert-butyl-4'-methoxydibenzoylmethane (INCI name: Butyl Methoxydibenzoylmethane).
  • the content of the compound(s) derived from dibenzoylmethane is between 0.1 % and 15% by weight, preferably between 0.2% and 10% by weight, more preferentially between 0.3% and 5% by weight, relative to the total weight of the composition.
  • the composition comprises at least one polymer comprising monomer units of formulae (A) and (B) defined below:
  • R1 is chosen from alkyl or alkenyl radicals, and at least 60% by weight of the Ri groups are radicals chosen from stearyl and behenyl radicals, the percentage by weight relating to the sum of all the Ri groups present in the polymer, and the weight ratio of the sum of all the hydroxyethyl acrylate units to the sum of all the acrylate units bearing the Ri group ranges from 1 :30 to 1 :1 , and the sum of the total of units A and B is at least 95% by weight relative to the total weight of the polymer.
  • Ri is constituted of alkyl radicals, preferably of C16-C22 alkyl radicals, and more preferentially of stearyl (Cis) radicals or of behenyl (C22) radicals.
  • At least 70% by weight of the groups R1 are stearyl or behenyl radicals, preferentially at least 80% by weight and more preferentially at least 90% by weight.
  • all the R1 groups are behenyl radicals.
  • all the R1 groups are stearyl radicals.
  • said weight ratio ranges from 1 :15 to 1 :1 and preferentially ranges from 1 :10 to 1 :4.
  • the polymer units present in the polymer consist of the units (A) and (B) previously described.
  • the polymer has a number-average molecular weight Mn ranging from 2000 to 9000 g/mol, preferably ranging from 5000 to 9000 g/mol.
  • the number-average molecular weight may be measured via the gel permeation chromatography method, for example according to the method described in the example hereinbelow.
  • the polymer has a melting point ranging from 40°C to 70°C and preferentially ranging from 45°C to 67°C.
  • the melting point is measured by differential scanning calorimetry (DSC), for example according to the method described in the example hereinbelow.
  • the polymer when the polymer is such that at least 60% by weight of the groups R1 are stearyl radicals, then the polymer preferably has a melting point ranging from 40 to 60°C, and preferentially ranging from 45 to 55°C.
  • the polymer when the polymer is such that at least 60% by weight of the groups R1 are behenyl radicals, then the polymer has a melting point ranging from 60°C to 70°C, and preferentially ranging from 63°C to 67°C.
  • the polymerization may be performed according to known methods, such as solution polymerization or emulsion polymerization.
  • the polymerization is, for example, described in document US 2007/0264204.
  • the acrylic polymer(s) as defined previously can be present in the composition according to the invention in a content of active material ranging from 0.05% to 10% by weight, relative to the total weight of the composition, preferably ranging from 0.1 % to 5% by weight and better still ranging from 0.2% to 3% by weight.
  • composition in accordance with the invention may comprise at least one fatty phase.
  • fatty phase means a phase comprising at least one fatty substance, in particular a liquid, solid or pasty fatty substance, and all of the liposoluble and lipophilic ingredients used for the formulation of the compositions of the invention.
  • the composition according to the invention comprises at least one oil.
  • oil is intended to mean any fatty substance that is in liquid form at ambient temperature (20-25°C) and atmospheric pressure (760 mmHg).
  • the fatty phase may comprise, in particular, at least one volatile or nonvolatile hydrocarbon-based oil and/or one volatile and/or non-volatile silicone oil and/or one volatile and/or non-volatile fluoro oil.
  • silicon oil is understood to mean an oil comprising at least one silicon atom, and in particular at least one Si-0 group.
  • hydrocarbon-based oil is intended to mean an oil mainly containing hydrogen and carbon atoms and optionally one or more heteroatoms, in particular nitrogen and oxygen.
  • these oils may in particular contain one or more carboxy, ester, ether, hydroxyl functions.
  • fluoro oil is intended to mean an oil comprising at least one fluorine atom.
  • volatile oil is intended to mean an oil that is capable of evaporating on contact with the skin or the keratin fibre in less than one hour, at ambient temperature and atmospheric pressure.
  • volatile oil(s) of the invention are volatile cosmetic oils, which are liquid at ambient temperature, having a non-zero vapour pressure, at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10 -3 to 300 mmHg), in particular ranging from 1 .3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • non-volatile oil is understood to mean an oil which remains on the skin or the keratin fibre, at ambient temperature and atmospheric pressure, for at least several hours and which has in particular a vapour pressure of less than 10’ 3 mmHg (0.13 Pa).
  • composition in accordance with the invention may comprise at least one ester of C2-C22 di- or tricarboxylic acid and of C1-C24 alcohols.
  • the C2-C22 di- or tricarboxylic acids are in particular chosen from citric acid, malic acid, malonic acid, succinic acid, adipic acid, maleic acid, fumaric acid, tartaric acid, isocitric acid, and mixtures thereof.
  • the acids are preferably citric acid and adipic acid, and even more preferentially the acid is citric acid.
  • the C1-C24 alcohols are not oxyalkylenated. They may be aliphatic, cyclic or aromatic, having from 1 to 24 carbon atoms. They are in particular chosen from phenol, benzyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, methanol, ethanol, propanol, n-butanol, t-butanol, pentanol and hexanol.
  • the alcohol(s) is/are C1-C6 alcohol(s) and can be chosen from methanol, ethanol, propanol, n-butanol, t-butanol, pentanol, hexanol, and even more preferentially the alcohol is ethanol.
  • the ester(s) of C2-C22 di- or tricarboxylic acid and of C1-C24 alcohols can be mono- or polyesterified.
  • Monoesterified is understood to mean that only one of the two or three carboxylic acid functions is esterified.
  • Polyesterified is understood to mean that at least two carboxylic acid functions are esterified.
  • the di- or tricarboxylic acid can be esterified with a number of different alcohols. It is preferably esterified with just one alcohol.
  • the composition comprises at least one ester of C3-C22 tricarboxylic acid and of C1-C24, preferably Ci- Ce, alcohols.
  • This/these ester(s) can be mono-, di- or triesterif ied.
  • Monoesterified is understood to mean that only one of the three carboxylic acid functions is esterified. Diesterified is understood to mean that two of the three carboxylic acid functions are esterified. Triesterified is understood to mean that all three carboxylic acid functions are esterified.
  • ester(s) of C3- C22 tricarboxylic acid and of Ci-Ce alcohols are triesterified.
  • ester(s) of C3- C22 tricarboxylic acid and of Ci-Ce alcohols are chosen from the compounds of formula (9) below:
  • R1, R2 and R3 represent, independently of each other, a hydrogen atom or a monovalent, saturated or unsaturated, aliphatic, cyclic or aromatic hydrocarbon-based group having from 1 to 6 carbon atoms;
  • R represents a hydrogen atom or a hydroxyl radical.
  • R1, R2 and R3 represent, independently of each other, a hydrogen atom or a linear or branched, substituted or unsubstituted, preferably unsubstituted, Ci-Ce alkyl radical, and in particular a radical chosen from methyl, ethyl, propyl, n-butyl, t-butyl, pentyl and hexyl radicals.
  • Ri , R2 and R3 are chosen, independently of each other, from a hydrogen atom and methyl, ethyl, propyl, n-butyl and t-butyl radicals.
  • the radicals R1, R2 and R3 are identical and are chosen from C-i-Ce, preferably C1-C4, alkyl radicals and even more preferentially are ethyl radicals.
  • R represents a hydroxyl radical
  • ester of tricarboxylic acid and of C-i-Ce alcohols has the following formula:
  • C12-C22 higher fatty acids such as oleic acid, linoleic acid or linolenic acid
  • carbonates such as dicaprylyl carbonate, such as the product sold under the name Cetiol CC® by the company Cognis; and mixtures thereof.
  • non-volatile hydrocarbon-based oils that may be used according to the invention, preference will be given more particularly to glyceride triesters and in particular to caprylic/capric acid triglycerides, synthetic esters and in particular diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, dicaprylyl carbonate, isononyl isononanoate, oleyl erucate, C12-C15 alkyl benzoate, 2- ethylphenyl benzoate and fatty alcohols, in particular octyldodecanol.
  • the non-volatile hydrocarbon-based oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate and dicaprylyl carbonate.
  • hydrocarbon-based oils that may be used according to the invention, mention may be made in particular of hydrocarbon-based oils containing from 8 to 16 carbon atoms and in particular of branched Cs-C alkanes, such as Cs- C isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane or isohexadecane, the oils sold under the Isopar or Permethyl trade names, branched Cs-C esters, isohexyl neopentanoate, and mixtures thereof.
  • Cs- C isoalkanes of petroleum origin also known as isoparaffins
  • isododecane also known as 2,2,4,4,6-pentamethylheptane
  • isodecane or isohexadecane the oils sold under the Isopar or Permethyl trade names
  • volatile hydrocarbon-based oils for instance petroleum distillates, in particular those sold under the name Shell Solt® by the company Shell, may also be used.
  • the volatile solvent is chosen from volatile hydrocarbon-based oils containing from 8 to 16 carbon atoms, and mixtures thereof.
  • the non-volatile silicone oils may be notably chosen from non-volatile polydimethylsiloxanes (PDMSs), polydimethylsiloxanes including alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, these groups each containing from 2 to 24 carbon atoms, or phenyl silicones, such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxysilicates.
  • PDMSs non-volatile polydimethylsiloxanes
  • phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphen
  • volatile silicone oils examples include volatile linear or cyclic silicone oils, in particular those with a viscosity ⁇ 8 centistokes (8x1 O’ 6 m 2 /s) and especially containing from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • volatile silicone oils that may be used in the invention, mention may notably be made of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.
  • a fatty phase according to the invention may also comprise other fatty substances, mixed with or dissolved in the oil.
  • Another fatty substance that may be present in the fatty phase may be, for example: a fatty acid chosen from fatty acids including from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; a wax chosen from waxes such as lanolin, beeswax, carnauba or candelilla wax, rice bran wax, paraffin waxes, lignite waxes, microcrystalline waxes, ceresin or ozokerite, or synthetic waxes, such as polyethylene waxes or Fischer-Tropsch waxes; a gum chosen from silicone gums (dimethiconol); a pasty compound, such as polymeric or non-polymeric silicone compounds, esters of a glycerol oligomer, arachidyl propionate, fatty acid triglycerides and derivatives thereof; and mixtures thereof.
  • a fatty acid chosen from fatty acids including from 8 to 30 carbon atoms such as ste
  • the overall fatty phase including all the lipophilic substances other than the lipophilic screening agents of the composition capable of being dissolved in this same phase, represents from 5% to 95% by weight and preferentially from 10% to 80% by weight, relative to the total weight of the composition.
  • composition in accordance with the invention may comprise at least one aqueous phase.
  • the aqueous phase contains water and optionally other water-soluble or water-miscible organic solvents.
  • An aqueous phase that is suitable for use in the invention may comprise, for example, a water chosen from a natural spring water, such as water from La Roche- Posay, water from Vittel, water from Saint Gervais Mont Blanc or waters from Vichy, or a floral water.
  • a natural spring water such as water from La Roche- Posay, water from Vittel, water from Saint Gervais Mont Blanc or waters from Vichy, or a floral water.
  • the overall aqueous phase including all the hydrophilic substances other than hydrophilic screening agents of the composition capable of being dissolved in this same phase, represents from 1 % to 99% by weight and preferentially from 10% to 80% by weight, relative to the total weight of the composition.
  • compositions according to the invention may also contain one or more additional UV-screening agents chosen from hydrophilic, lipophilic or insoluble organic UV-screening agents and/or one or more mineral pigments. It will preferentially be constituted of at least one hydrophilic, lipophilic or insoluble organic UV-screening agent.
  • hydrophilic UV-screening agent is intended to mean any cosmetic or dermatological organic or inorganic compound for screening out UV radiation, which can be fully dissolved in molecular form in a liquid aqueous phase or else which can be dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
  • lipophilic screening agent is intended to mean any cosmetic or dermatological organic or inorganic compound for screening out UV radiation, which can be fully dissolved in molecular form in a liquid fatty phase or else which can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.
  • insoluble UV-screening agent is intended to mean any cosmetic or dermatological organic or inorganic compound for screening out UV radiation which has a solubility in water of less than 0.5% by weight and a solubility of less than 0.5% by weight in the majority of 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 determined at 70°C, is defined as the amount of product in solution in the solvent at equilibrium with an excess of solid in suspension after returning to ambient temperature. It may be readily evaluated in the laboratory.
  • the additional organic UV-screening agents are chosen in particular from cinnamic compounds; anthranilate compounds; salicylic compounds; benzylidenecamphor compounds; benzophenone compounds; f3, [3-diphenylacrylate compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in patent US 5 624 663; benzimidazole derivatives; imidazoline compounds; bis-benzazolyl compounds, as described in patents EP 669 323 and US 2 463 264; p-aminobenzoic (PABA) compounds; methylenebis(hydroxyphenylbenzotriazole) compounds, as described in patent applications US 5 237 071 , US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 119; benzoxazole compounds, as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening
  • Cinnamic compounds Ethylhexyl methoxycinnamate sold in particular under the trade name Parsol MCX® by DSM Nutritional Products,
  • Neo Heliopan E 1000® Isoamyl p-Methoxycinnamate, sold under the trade name Neo Heliopan E 1000® by Symrise,
  • Ethylhexyl Dimethyl PABA sold in particular under the name Escalol 507® by ISP,
  • PEG-25 PABA sold under the name llvinul P 25® by BASF.
  • Ethylhexyl Salicylate sold under the name Neo Heliopan OS® by Symrise
  • Dipropylene Glycol Salicylate sold under the name Dipsal® by Scher
  • TEA Salicylate sold under the name Neo Heliopan TS® by Symrise.
  • Octocrylene sold in particular under the trade name llvinul N 539® by BASF
  • Etocrylene sold in particular under the trade name Uvinul N 35® by BASF.
  • Benzophenone-1 sold under the trade name Uvinul 400® by BASF,
  • Benzophenone-2 sold under the trade name Uvinul D 50® by BASF
  • Benzophenone-3 or Oxybenzone sold under the trade name llvinul M 40® by BASF
  • Benzophenone-4 sold under the trade name llvinul MS 40® by BASF,
  • Benzophenone-6 sold under the trade name Helisorb 11® by Norquay,
  • Benzophenone-8 sold under the trade name Spectra-Sorb UV-24® by American Cyanamid,
  • Benzophenone-9 sold under the trade name Uvinul DS 49® by BASF,
  • Benzophenone-12, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate sold under the trade name Uvinul A Plus® or, as a mixture with octyl methoxycinnamate, under the trade name Uvinul A Plus B® by the company BASF,
  • Camphor Benzalkonium Methosulfate manufactured under the name Mexoryl SO® by Chimex,
  • Phenylbenzimidazole compounds Phenylbenzimidazole Sulfonic Acid, sold in particular under the trade name Eusolex 232® by Merck.
  • Neo Heliopan AP® Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the trade name Neo Heliopan AP® by Haarmann and Reimer.
  • Methylene bis-Benzotriazolyl Tetramethylbutylphenol in particular in solid form, such as the product sold under the trade name Mixxim BB/100® by Fairmount Chemical, or in the form of an aqueous dispersion of micronized particles with a mean particle size ranging from 0.01 to 5 pm, more preferentially from 0.01 to 2 pm and more particularly from 0.020 to 2 pm, with at least one alkylpolyglycoside surfactant having the structure CnH2n+iO(CeHio05)xH, in which n is an integer from 8 to 16 and x is the mean degree of polymerization of the (CeH-ioOs) unit and ranges from 1.4 to 1.6, as described in patent GB-A-2 303549, sold in particular under the trade name Tinosorb M® by BASF, or in the form of an aqueous dispersion of micronized particles with a mean particle size ranging from 0.02 to 2 pm, more preferentially from 0.01 to 1.5 pm and
  • Ethylhexyl Triazone sold in particular under the trade name llvinul T 150® by BASF,
  • Anthranilic compounds Menthyl anthranilate, sold under the trade name Neo Heliopan MA® by Symrise.
  • Polyorganosiloxane comprising benzalmalonate functions such as Polysilicone-15, sold under the trade name Parsol SLX® by Hoffmann-La Roche.
  • the preferential organic screening agents are chosen from:
  • the particularly preferred organic screening agents are chosen from:
  • the inorganic UV-screening agents used in accordance with the present invention are metal oxide pigments. More preferentially, the inorganic UV-screening agents of the invention are metal oxide particles with a mean elementary particle size of less than or equal to 0.5 pm, more preferentially between 0.005 and 0.5 pm, even more preferentially between 0.01 and 0.2 pm, better still between 0.01 and 0.1 pm and more particularly between 0.015 and 0.05 pm.
  • They may be chosen in particular from titanium oxide, zinc oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
  • Such coated or uncoated metal oxide pigments are described in particular in patent application EP-A-0 518 773.
  • Commercial pigments that may be mentioned include the products sold by the companies Sachtleben Pigments, Tayca, Merck and Degussa.
  • the metal oxide 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 such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (of titanium or aluminium), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
  • compounds such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (of titanium or aluminium), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
  • the coated pigments are more particularly titanium oxides that have been coated: with silica, such as the product Sunveil® from the company Ikeda, with silica and iron oxide, such as the product Sunveil F® from the company Ikeda, with silica and alumina, such as the products Microtitanium Dioxide MT 500 SA® and Microtitanium Dioxide MT 100 SA from the company Tayca and Tioveil from the company Tioxide, 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 Sachtleben Pigments, with alumina and aluminum stearate, such as the products Microtitanium Dioxide MT 100 T®, MT 100 TX®, MT 100 Z® and MT-01® from the company Tayca, the products Solaveil CT-10 W® and Solaveil CT 100® from the company Uniqema and the
  • TiO2 treated with a polydimethylsiloxane sold under the trade name 70250 Cardre UF TiO2SI3® by the company Cardre, anatase/rutile TiCh treated with a polydimethylhydrosiloxane, sold under the trade name Micro Titanium Dioxide USP Grade Hydrophobic® by the company Color Techniques,
  • TiO2 pigments doped with at least one transition metal such as iron, zinc or manganese and more particularly manganese.
  • said doped pigments are in the form of an oily dispersion.
  • the oil present in the oily dispersion is preferably chosen from triglycerides including those of capric/caprylic acids.
  • the oily dispersion of titanium oxide particles may also comprise one or more dispersants, for instance a sorbitan ester, for instance sorbitan isostearate, or a polyoxyalkylenated fatty acid ester of glycerol, for instance TRI-PPG- 3 myristyl ether citrate and polyglyceryl-3 polyricinoleate.
  • the oily dispersion of titanium oxide particles includes at least one dispersant chosen from polyoxyalkylenated fatty acid esters of glycerol. Mention may be made more particularly of the oily dispersion of TiO2 particles doped with manganese in capric/caprylic acid triglyceride in the presence of TRI-PPG-3 myristyl ether citrate and polyglyceryl-3 polyricinoleate and sorbitan isostearate having the INCI name: titanium dioxide (and) TRI-PPG-3 myristyl ether citrate (and) polyglyceryl-3 ricinoleate (and) sorbitan isostearate, for instance the product sold under the trade name Optisol TD50® by the company Croda.
  • 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 Wackher under the name Transparent titanium oxide PW®, by the company Miyoshi Kasei under the name LIFTR®, 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: those sold under the name Z-Cote by the company Sunsmart; those sold under the name Nanox® by the company Elementis; those sold under the name Nanogard WCD 2025® by the company Nanophase Technologies.
  • the coated zinc oxide pigments are for example: those sold under the name Oxide Zinc CS-5® by the company Toshibi (ZnO coated with polymethylhydrosiloxane); 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); those sold under the name Daitopersion Zn-30® and Daitopersion Zn-50® by the company Daito (dispersions in cyclopolymethylsiloxane/oxyethylenated polydimethylsiloxane, containing 30% or 50% of zinc oxides coated with silica and polymethylhydrosiloxane); those sold under the name NFD Ultrafine ZnO® by the company Daikin (ZnO coated with perfluoroalkyl phosphate and copolymer based on perfluoroalkylethyl as a dispersion in cyclopentasiloxan
  • the uncoated cerium oxide pigments may be, for example, those sold 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®.
  • mixtures of metal oxides especially of titanium dioxide and of cerium dioxide, including the equal-weight mixture of titanium dioxide and cerium dioxide coated with silica, sold by the company Ikeda under the name Sunveil A®, and also the mixture of titanium dioxide and zinc dioxide coated with alumina, silica and silicone, such as the product M 261® sold by the company Sachtleben Pigments, or coated with alumina, silica and glycerol, such as the product M 211® sold by the
  • coated or uncoated titanium oxide pigments are particularly preferred.
  • the additional UV-screening agents according to the invention can be present in the composition according to the invention in a content ranging from 0.1 % to 60% by weight and in particular from 5% to 30% by weight relative to the total weight of the composition.
  • composition in accordance with the present invention may also comprise conventional cosmetic adjuvants chosen in particular from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preservatives, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, basifying or acidifying agents or any other ingredient commonly used in the cosmetic and/or dermatological field.
  • conventional cosmetic adjuvants chosen in particular from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preservatives, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants
  • short-chain monoalcohols for example C1-C4 monoalcohols such as ethanol and isopropanol, short-chain C2-C8 polyols, such as glycerol or diols, such as caprylyl glycol, 1 ,2- pentanediol, propanediol, butanediol, glycols and glycol ethers, such as ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol or diethylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, sorbitol, and mixtures thereof.
  • C1-C4 monoalcohols such as ethanol and isopropanol
  • short-chain C2-C8 polyols such as glycerol or diols
  • caprylyl glycol 1 ,2- pentanediol, propanediol, butan
  • use may be made more particularly of ethanol, propylene glycol, glycerol, and mixtures thereof.
  • carboxyvinyl polymers such as the Carbopols® (Carbomers) and the Pemulens, such as Pemulen TR1® and Pemulen TR2® (acrylate/C10-C30 alkyl acrylate copolymer); polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel 305® (CTFA name: polyacrylamide/Ci3-i4 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyl taurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, such as the poly(2- acrylamido-2-methylpropanesulfonic acid) sold by the company Hoechst under the trade name Hostacerin
  • acidifying agents examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • mineral or organic acids for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • basifying agents examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines, such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide or potassium hydroxide.
  • the cosmetic composition comprises one or more basifying agents chosen from alkanolamines, in particular triethanolamine, and sodium hydroxide.
  • active agents for caring for keratin materials such as the skin, the lips, the scalp, the hair, the eyelashes or the nails
  • compositions according to the invention may be aqueous or anhydrous.
  • compositions are aqueous, they contain at least one aqueous phase.
  • compositions according to the invention may then be provided in purely aqueous form, that is to say that they comprise an amount of fatty phase of less than 10% by weight, preferably of less than 5% by weight, and more preferentially still of less than 2% by weight, relative to the total weight of the composition.
  • the composition according to the invention is essentially aqueous, that is to say that it is devoid of fatty phase.
  • compositions according to the invention may also 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.
  • a simple or complex emulsion O/W, W/O, O/W/O or W/O/W
  • the pH is generally between 3 and 12 approximately, preferably between 5 and 9 approximately, and even more particularly from 5.5 to 8.
  • compositions may also be in anhydrous form, for instance in the form of an oil, a glycolic solution or an alcoholic solution.
  • anhydrous composition is intended to mean a composition containing less than 1 % by weight of water, or even less than 0.5% water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients. They may optionally be packaged in aerosol form and may be in the form of a mousse or a spray.
  • compositions in the form of oil-in-water or water-in-oil emulsions are of the paddle or impeller, rotor-stator and HPH type.
  • 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/O or O/W emulsion).
  • W/O emulsifying surfactants examples include alkyl esters or ethers of sorbitan, of glycerol, of polyol, of glycerol or of sugars; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, sold under the name DC 5225 C® by the company Dow Coming, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Coming; 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 09® by
  • non-silicone emulsifying surfactants in particular alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars.
  • Polyol alkyl esters that may in particular 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 examples include 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.
  • non-ionic emulsifying surfactants examples include polyoxyalkylenated (more particularly polyoxyethylenated and/or polyoxypropylenated) esters of fatty acids and of glycerol; oxyalkylenated esters of fatty acids and of sorbitan; polyoxyalkylenated (in particular polyoxyethylenated and/or polyoxypropylenated) esters of fatty acids, optionally in combination with an ester of a fatty acid and of glycerol, such as the PEG-100 stearate/glyceryl stearate mixture sold, for example, by the company 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
  • the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, for example as described in the document WO-A-92/06778.
  • the aqueous phase of this emulsion may comprise a non-ionic 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, in particular cosmetic treatments, for the skin, the lips and the hair, including the scalp, in particular for protecting and/or caring for the skin, the lips and/or the hair, and/or for making up the skin and/or the lips.
  • compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, the lips, the nails, the hair, the eyelashes, the eyebrows and/or the scalp, in particular care products, antisun products and makeup products.
  • compositions according to the invention may be used, for example, as a makeup product.
  • Another subject of the present invention is constituted of a non- therapeutic cosmetic process for caring for and/or making up a keratin material, which consists in applying, to the surface of said keratin material, at least one composition according to the invention as defined above.
  • Another subject of the invention consists of the use of pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate to photostabilize a merocyanine of formula (3) as defined above.
  • Another subject of the invention consists of the use of pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate to photostabilize a merocyanine of formula (3) as defined above in the presence of one or more dibenzoylmethane derivatives, preferably in the presence of 4-(tert-butyl)-4'-methoxydibenzoylmethane.
  • compositions according to the invention may be used, for example, as a care product and/or antisun product for the face and/or body, with a liquid to semi-liquid consistency, such as milks, more or less smooth creams, cream gels or pastes. They may optionally be packaged in aerosol form and may be in the form of a mousse 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 hair in the form of fine particles by means of pressurizing 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 aerosol pumps using compressed air as propellant. These devices are described in patents US 4 077 441 and US 4 850 517.
  • compositions packaged in aerosol form in accordance with the invention generally contain conventional propellants, for instance 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.
  • the invention also relates to a cosmetic assembly comprising: a container delimiting one or more compartments, said container being closed by a closing member and optionally being unsealed; and a makeup and/or care composition in accordance with the invention placed inside said compartment(s).
  • the container may be, for example, in the form of a jar or a box.
  • the closing member may be in the form of a lid comprising a cap mounted so as to be able to move by translation or by pivoting relative to the container housing said makeup and/or care composition(s).
  • the completion of the alkylation reaction can be monitored for example by methods such as TLC, GC or HPLC.
  • the sample is prepared by preparing a solution of the polymer at 10 mg/ml in tetrahydrofuran. The sample is placed in an oven at 54°C for 10 minutes and then in an oscillating shaker for 60 minutes to aid dissolution. After visual inspection, the sample appears to be totally dissolved in the solvent.
  • the sample prepared was analysed using two polypore 300x7.5 mm columns (manufactured by Agilent Technologies), a Waters 2695 chromatographic system, a tetrahydrofuran mobile phase and detection by refractive index.
  • the sample was filtered through a 0.45 pm nylon filter, before being injected into the liquid chromatograph.
  • the standards used for the calibration are the Easi Vial narrow polystyrene (PS) standards from Agilent Technologies.
  • the system is equipped with a PSS SECcurity 1260 Rl detector.
  • the polystyrene calibration curve was used to determine the average molecular weight.
  • the recording of the diagrams and the determination of the various molecular weights were performed by the Win GPC Unichrom 81 program.
  • This method describes the general procedure for determining the melting point of polymers by differential scanning calorimetry. This method is based on the standards ASTM E791 and ASTM D 34182 and the DSC calibration is performed according to standard ASTM E 9672.
  • the solvent was then removed by vacuum distillation, 1 g of dilauryl peroxide was then added and the reaction was continued for 60 minutes at 110°C. The step was repeated. The mixture was then cooled to 90°C, a stream of demineralized water was added and the mixture was then stirred. The water was removed by vacuum distillation.
  • the solvent was then removed by vacuum distillation, 1 g of dilauryl peroxide was then added and the reaction was continued for 60 minutes at 125°C. The step was repeated. The mixture was then cooled to 90°C, a stream of demineralized water was added and the mixture was then stirred. The water was removed by vacuum distillation.
  • compositions 1 and 2 are prepared from the ingredients indicated in the table below, the amounts of which are expressed in % by weight of starting material (SM) relative to the total weight of the composition.
  • Phase A1 is prepared by mixing all of the ingredients, and then phase A2 is added for neutralization and gel formation. This is followed by addition of phase A3. All of this preparation of the phase, which will be referred to as A hereinafter, is carried out while heating to 65°C and with stirring with blades (50 rpm).
  • Phase B is prepared by mixing all of the ingredients while heating to 80°C with magnetic stirring until a clear and homogeneous phase is obtained.
  • Emulsification is carried out by dispersing phase B in phase A at 65°C and with intense stirring (blades at 80 rpm and turbine at 11 000 rpm) for 5 minutes. An oil-in-water emulsion is obtained. The temperature of the mixture is then reduced gradually to return to ambient temperature, while maintaining the same level of stirring until the end. At around 55°C, the thickeners of phase C are added (5 minutes), and then phase D (5 minutes) and the fillers of phase E starting from 35°C. Lastly, the alcohol of phase F is added once the mixture has returned to ambient temperature.
  • Compositions 1 and 2 are each spread over 6 Europlast brand PMMA plates at a rate of 2.0 to 2.1 mg/cm 2 (which corresponds to between 16 and 17 mg over 8 cm 2 ). 3 of the 6 plates are then exposed in a Suntest (Heraeus) with a UV dose of 43.2 J/cm 2 at a temperature of 40°C, while the others are stored at the same temperature in the dark.
  • Suntest Heraeus
  • Composition 2 according to the invention exhibits a residual fraction of merocyanine compound that is substantially greater than that of Comparative Composition 1 , which shows that, in the presence of pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate, the merocyanine compound exhibits better photostability with respect to UV radiation.

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Abstract

La présente invention concerne une composition, en particulier une composition cosmétique ou dermatologique, comprenant : a) au moins une mérocyanine répondant à la formule (3) ci-dessous ainsi que ses formes isomères géométriques, en particulier formes isomères géométriques E/E ou E/Z : Formule (3) dans laquelle : A représente -O- ou –NH ; R représente un groupe alkyle en C1-C22, un groupe alcényle en C2-C22, un groupe alcynyle en C2-C22, un groupe cycloalkyle en C3-C22 ou un groupe cycloalcényle en C3-C22, lesdits groupes pouvant être interrompus par un ou plusieurs O ; et b) du pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate. La présente invention concerne en outre un procédé cosmétique non thérapeutique pour le soin et/ou le maquillage d'une matière kératinique, comprenant l'application, à la surface de ladite matière kératinique, d'au moins une composition telle que définie ci-dessus.
PCT/EP2022/085446 2021-12-17 2022-12-12 Composition cosmétique ou dermatologique comprenant une mérocyanine et du pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate WO2023110777A1 (fr)

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US5166355A (en) 1991-02-04 1992-11-24 Fairmount Chemical Co., Inc. Process for preparing substituted 2,2'-methylene-bis-[6-(2H-benzotriazol-2-yl)-4-hydrocarbyl-phenols]
EP0518773A1 (fr) 1991-06-14 1992-12-16 L'oreal Composition cosmétique contenant un mélange de nanopigments d'oxydes métalliques et de pigments mélaniques
WO1993004665A1 (fr) 1991-08-29 1993-03-18 L'oreal Composition cosmetique filtrante contenant un polymere filtre liposoluble a structure hydrocarbonee et une silicone filtre
US5237071A (en) 1991-01-22 1993-08-17 Fairmount Chemical Company, Inc. Process for preparing 2,2'-methylene-bis(6-(2H-benzotriazol-2-yl)-4-hydrocarbyl phenols)
EP0669323A1 (fr) 1994-02-24 1995-08-30 Haarmann & Reimer Gmbh Utilisation de benzazolen comme absorbeurs d'UV nouveaux benzazoles et procédé pour les préparation
GB2303549A (en) 1995-07-22 1997-02-26 Ciba Geigy Ag Micronising organic UV absorbers with alkyl polyglucosides
US5624663A (en) 1987-08-28 1997-04-29 L'oreal Photostable cosmetic filter composition cotaining a UV-A filter and a substituted dialkylbenzalmalonate, the use of substituted dialkylbenzalmalonates in cosmetics as broad-band solar filters and novel substituted dialkyl malonates
EP0832642A2 (fr) 1996-09-13 1998-04-01 3V SIGMA S.p.A Dérivés de benzoxazole et utilisation comme filtres ultraviolet
EP0841341A1 (fr) 1996-11-08 1998-05-13 L'oreal Nouveaux filtres solaires, compositions cosmétiques photoprotectrices les contenant et utilisations
DE19726184A1 (de) 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an lichtschutzwirksamen Benzotriazolderivaten
EP0893119A1 (fr) 1997-07-26 1999-01-27 Ciba SC Holding AG Formulation protectrice contre UV
DE19746654A1 (de) 1997-08-13 1999-02-18 Basf Ag Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen
DE19755649A1 (de) 1997-12-15 1999-06-17 Basf Ag Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen
EP0967200A1 (fr) 1998-06-26 1999-12-29 Basf Aktiengesellschaft 4,4-Diarylbutadiènes comme filtres UV hydrosolubles et photostables pour préparations cosmétiques et pharmaceutiques
DE19855649A1 (de) 1998-12-03 2000-06-08 Basf Ag Dimere alpha-Alkyl-Styrolderivate als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen
EP1008586A1 (fr) 1998-12-11 2000-06-14 Basf Aktiengesellschaft Diarylbutadiènes oligomères
EP1027883A2 (fr) 1999-01-11 2000-08-16 3V SIGMA S.p.A Combinaison des agents antisolaires contre les rayonnements UV-A et UV-B
US6225467B1 (en) 2000-01-21 2001-05-01 Xerox Corporation Electroluminescent (EL) devices
EP1133980A2 (fr) 2000-03-15 2001-09-19 Basf Aktiengesellschaft Utilisation d'une combinaison d'agents photoprotecteurs comprenant en tant que composé essentiel des hydroxybenzophénones aminosubstituées comme filtres UV photostables dans des préparations cosmétiques et pharmaceutiques
EP1300137A2 (fr) 2001-10-02 2003-04-09 3V SIGMA S.p.A Combinations d'agents anti-solaires
DE10162844A1 (de) 2001-12-20 2003-07-03 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Bis-Resorcinyltriazinderivaten und Benzoxazol-Derivaten
WO2004006878A1 (fr) 2002-07-10 2004-01-22 Ciba Specialty Chemicals Holding Inc. Derives de merocyanine a usage cosmetique
WO2004085412A2 (fr) 2003-03-24 2004-10-07 Ciba Specialty Chemicals Holding Inc. Derives de triazine symetriques
WO2006034982A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Concentre photoprotecteur a micropigments organiques
WO2006034991A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion eau dans l'huile contenant des pigments filtrants de protection solaire anti-uv
WO2006034992A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion cosmetique de protection solaire contenant des micropigments organiques
WO2006035000A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion photoprotectrice a teneur elevee en pigments filtrants, photoprotecteurs
WO2006034985A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion huile dans l'eau contenant des pigments filtrants de protection solaire anti-uv inorganiques et du sulfate d'alkyle
WO2006035007A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Preparation cosmetique de protection solaire a base de micropigments
WO2007068371A1 (fr) 2005-12-14 2007-06-21 Cognis Ip Management Gmbh Procede pour produire des hydrocarbures
WO2007071582A1 (fr) 2005-12-20 2007-06-28 Ciba Holding Inc. Dérivés de mérocyanine
WO2007071584A2 (fr) 2005-12-21 2007-06-28 Ciba Holding Inc. Utilisation de colorants de transmission
US20070264204A1 (en) 2006-05-11 2007-11-15 Air Products And Chemicals, Inc. Personal care compositions containing functionalized polymers
WO2008155059A2 (fr) 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
WO2009063392A2 (fr) 2007-11-12 2009-05-22 Basf Se Composition en dispersion aqueuse d'absorbeurs de lumière ultraviolette
WO2013011094A2 (fr) 2011-07-21 2013-01-24 L'oreal Composition cosmétique et/ou dermatologique contenant un dérivé de mérocyanine comportant des groupes polaires spécifiques constitués de fonctionnalités hydroxyle et éther
US8454940B2 (en) * 2007-08-24 2013-06-04 Basf Se Mixtures comprising benzotriazoles and merocyanines
WO2020002537A1 (fr) * 2018-06-28 2020-01-02 L'oreal Composition cosmétique ou dermatologique comprenant une mérocyanine et une phase huileuse comprenant au moins un carbonate d'alkyle ou d'alkylène
FR3111074A1 (fr) * 2020-06-08 2021-12-10 L'oreal Composition à base de rétinol

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DE19726184A1 (de) 1997-06-20 1998-12-24 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an lichtschutzwirksamen Benzotriazolderivaten
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DE19855649A1 (de) 1998-12-03 2000-06-08 Basf Ag Dimere alpha-Alkyl-Styrolderivate als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen
EP1008586A1 (fr) 1998-12-11 2000-06-14 Basf Aktiengesellschaft Diarylbutadiènes oligomères
EP1027883A2 (fr) 1999-01-11 2000-08-16 3V SIGMA S.p.A Combinaison des agents antisolaires contre les rayonnements UV-A et UV-B
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EP1133980A2 (fr) 2000-03-15 2001-09-19 Basf Aktiengesellschaft Utilisation d'une combinaison d'agents photoprotecteurs comprenant en tant que composé essentiel des hydroxybenzophénones aminosubstituées comme filtres UV photostables dans des préparations cosmétiques et pharmaceutiques
EP1300137A2 (fr) 2001-10-02 2003-04-09 3V SIGMA S.p.A Combinations d'agents anti-solaires
DE10162844A1 (de) 2001-12-20 2003-07-03 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Bis-Resorcinyltriazinderivaten und Benzoxazol-Derivaten
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WO2006034982A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Concentre photoprotecteur a micropigments organiques
WO2006034991A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion eau dans l'huile contenant des pigments filtrants de protection solaire anti-uv
WO2006034992A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion cosmetique de protection solaire contenant des micropigments organiques
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US8454940B2 (en) * 2007-08-24 2013-06-04 Basf Se Mixtures comprising benzotriazoles and merocyanines
WO2009063392A2 (fr) 2007-11-12 2009-05-22 Basf Se Composition en dispersion aqueuse d'absorbeurs de lumière ultraviolette
WO2013011094A2 (fr) 2011-07-21 2013-01-24 L'oreal Composition cosmétique et/ou dermatologique contenant un dérivé de mérocyanine comportant des groupes polaires spécifiques constitués de fonctionnalités hydroxyle et éther
WO2020002537A1 (fr) * 2018-06-28 2020-01-02 L'oreal Composition cosmétique ou dermatologique comprenant une mérocyanine et une phase huileuse comprenant au moins un carbonate d'alkyle ou d'alkylène
FR3111074A1 (fr) * 2020-06-08 2021-12-10 L'oreal Composition à base de rétinol

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