WO2023156298A1 - Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique - Google Patents

Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique Download PDF

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Publication number
WO2023156298A1
WO2023156298A1 PCT/EP2023/053301 EP2023053301W WO2023156298A1 WO 2023156298 A1 WO2023156298 A1 WO 2023156298A1 EP 2023053301 W EP2023053301 W EP 2023053301W WO 2023156298 A1 WO2023156298 A1 WO 2023156298A1
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Prior art keywords
acid
methoxypropyl
composition according
amino
ylidene
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PCT/EP2023/053301
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English (en)
Inventor
Cécile Boschet
Martin Josso
Flavie GILLANT
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L'oreal
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Publication of WO2023156298A1 publication Critical patent/WO2023156298A1/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
    • A61K8/18—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
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds thereof
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K2800/59—Mixtures

Definitions

  • the present invention relates to a cosmetic or dermatological composition
  • a cosmetic or dermatological composition comprising at least one merocyanine of formula (3) which will be defined below in detail and at least one polyionic complex containing at least one cationic polysaccharide and at least one crosslinking agent chosen from non-polymeric acids having at least three pKa values and their salts.
  • the present invention also relates to the use of at least one such merocyanine of formula (3) for reducing the staining of fabrics, in particular of clothing, after washing.
  • UVA rays with a wavelength 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, nonuniformity of the complexion).
  • UVA and UVB radiation Protection against UVA and UVB radiation is thus necessary.
  • An effective photoprotective product must protect against both UVA and UVB radiation.
  • photoprotective compositions have been proposed to date to overcome the effects induced by UVA and/or UVB radiation. They 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 fat-soluble 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 the 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 can 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 pre-existing melanin resulting in the darkening of the colour of the skin.
  • compositions containing a particular combination of UV-screening agents which would be especially suitable for the 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 which is already pigmented, for the purpose of not enhancing 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 range of wavelengths between 280 and 370 nm.
  • the desired photoprotective compounds must also exhibit good cosmetic properties, good solubility in the usual solvents and in particular in fatty substances, such as oils, and also good photostability, alone or in combination with other UV-screening agents. They must also be colourless or at least exhibit a colour which is cosmetically acceptable to the consumer.
  • sunscreens and in particular those which protect against UVA rays, are well known to a person skilled in the art as leaving yellow marks on clothing, these yellow marks being very difficult to remove during washing.
  • WO 2013/153678 and JP-A-2014-227389 the use of a film produced from a polyionic complex for cosmetic purposes is proposed in, for example, WO 2013/153678 and JP-A-2014-227389.
  • the film disclosed in WO 2013/153678 and JP-A-2014-227389 can provide certain cosmetic effects.
  • a dispersion comprising a polyionic complex is not always stable.
  • a dispersion comprising a polyionic complex has a tendency to be unstable at a high temperature, such as 45°C or more. If the dispersion is unstable, the polyionic complex tends to precipitate and consequently the dispersion can cause a phase separation.
  • a cationic polysaccharide can be used as cationic polymer.
  • a cationic polysaccharide can be added to a combination of an anionic polymer and of a cationic polymer.
  • a cationic polysaccharide can be used alone with at least one crosslinking agent chosen from non-polymeric acids having three or more acid groups and their salts to form a gel which is a dynamically and ionically crosslinked gel, which is abbreviated to DIC gel.
  • the DIC gel which is preferably in the form of particles, can also form water-resistant insoluble films.
  • composition comprising merocyanines of formula (3) defined below and a polyionic complex containing at least one cationic polysaccharide and at least one crosslinking agent chosen from non-polymeric acids having at least three pKa values and their salts exhibits good stability, good sunscreening effectiveness, good cosmetic quality and good film-forming properties.
  • compositions in particular a cosmetic or dermatological composition, comprising at least one merocyanine of formula (3) which will be defined below in detail and at least one polyionic complex containing at least one cationic polysaccharide and at least one crosslinking agent chosen from non-polymeric acids having at least three pKa values and their salts.
  • This composition makes it possible in particular to obtain an anti-sun product which exhibits good film-forming properties while not exhibiting the disadvantage of irreversibly staining clothing or other fabrics.
  • composition in accordance with the invention exhibits a good cosmetic quality of the composition comprising the merocyanines, said composition being in particular non-greasy and non-tacky.
  • Another subject-the matter of the present invention is the use of at least one merocyanine of formula (3) which will be defined in detail below for reducing the staining of fabrics, in particular clothing.
  • the present invention also relates to a non-therapeutic cosmetic method 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.
  • It also relates to a non-therapeutic cosmetic method for limiting the darkening of the skin and/or improving the colour and/or the uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined above.
  • the present invention also relates to a non-therapeutic cosmetic method 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 above.
  • composition according to the invention is intended for topical application and thus contains a physiologically acceptable medium.
  • physiologically acceptable medium is understood here to mean a medium which is compatible with keratin materials.
  • keratin material is understood to mean in particular the skin, scalp, keratin fibres, such as the eyelashes, eyebrows, head hair and body hair, nails, mucous membranes, such as the lips, and more particularly the skin and mucous membranes (body, face, area around the eyes, eyelids, lips, preferably body, face and lips).
  • to prevent or "prevention” is understood to mean, according to the invention, the fact of reducing the risk of onset or of slowing down the onset of a given phenomenon, namely, according to the present invention, the signs of ageing of a keratin material.
  • organic UVA-screening agent is understood to mean any organic chemical molecule capable of absorbing at least UVA radiation in the range of wavelengths of between 320 and 400 nm; it being possible for said molecule to also absorb, in addition, UVB radiation in the range of wavelengths of between 280 and 320 nm.
  • organic UVB-screening agent is understood to mean any organic chemical molecule capable of absorbing exclusively UVB radiation in the range of wavelengths of between 280 and 320 nm.
  • composition in accordance with the invention comprises at least one UVA-screening agent of merocyanine type as defined below.
  • A is -O- or -NH
  • R is a C 1 -C 22 alkyl group, a C 2 -C 22 alkenyl group, a C 2 -C 22 alkynyl group, a C 3 -C 22 cycloalkyl group or a C 3 -C 22 cycloalkenyl group, it being possible for said groups to be interrupted by one or more O.
  • the merocyanine compounds of the invention can be in their E/E or E/Z geometrical isomer forms;
  • A is -O-;
  • R is a C 1 -C 22 alkyl, which can be interrupted by 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 can 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, with respect to the total weight of the composition.
  • the compounds of formula (3) can be prepared according to the protocols described in Pat. Appl. 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)amino]cyclohex-2-en-1-ylidene ⁇ ethanoate (25) can be synthesized according to the synthesis scheme described in the publication by B. Winkler et al., Tetrahedron Letters, 55 (2014) 1749-1751, which is entitled “A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure”, and represented below, for the compounds of formula (3):
  • composition in accordance with the invention comprises at least one polyionic complex containing at least one cationic polysaccharide and at least one crosslinking agent chosen from non-polymeric acids having at least three pKa values and their salts.
  • composition according to the present invention comprises at least one polyionic complex.
  • Two or more different types of polyionic complexes can be used in combination.
  • a single type of polyionic complex or a combination of different types of polyionic complexes can be used.
  • the amount of polyionic complexes in the composition according to the present invention can be of 0.01% by weight or more, preferably 0.05% by weight or more and more preferentially 0.1% by weight or more, with respect to the total weight of the composition.
  • the amount of polyionic complexes in the composition according to the present invention can be of 25% by weight or less, preferably 20% by weight or less and more preferably 15% by weight or less, with respect to the total weight of the composition.
  • the amount of polyionic complexes in the composition according to the present invention can be of 0.01% to 25% by weight, preferably from 0.05% to 20% by weight and more preferentially from 0.1% to 15% by weight, with respect to the total weight of the composition.
  • polyionic complex itself is amphiphilic and insoluble in a fatty substance such as an oil or in water.
  • composition according to the present invention comprises at least one cationic polysaccharide.
  • Two or more different types of cationic polysaccharides can be used in combination.
  • a single type of cationic polysaccharide or a combination of different types of cationic polysaccharides can be used.
  • the cationic polysaccharide(s) have a positive charge density.
  • the charge density of the cationic polysaccharides can be from 0.01 meq/g to 20 meq/g, preferably from 0.05 to 15 meq/g and more preferably from 0.1 to 10 meq/g.
  • lt may be preferable for the molecular weight of the cationic polysaccharide(s) to be of 500 or more, preferably of 1000 or more, more preferably of 2000 or more and more preferably still of 5000 or more.
  • molecular weight means a number-average molecular weight.
  • the cationic polysaccharide(s) can have at least one positively chargeable and/or positively charged group chosen from primary, secondary or tertiary amino groups, quaternary ammonium groups, a guanidine group, a biguanide group, an imidazole group, an imino group and a pyridyl group.
  • the composition comprises at least one cationic polysaccharide having at least one quaternary ammonium group.
  • the cationic polysaccharide(s) can be homopolymers or copolymers.
  • copolymers is understood to mean both the copolymers obtained from two types of monomer and those obtained from more than two types of monomers, such as the terpolymers obtained from three types of monomers.
  • the cationic polysaccharide(s) can be chosen from natural and synthetic cationic polysaccharides.
  • the composition comprises at least one cationic cellulose polymer.
  • cationic cellulose polymers are the following.
  • Cationic cellulose polymers such as cellulose ether derivatives comprising one or more quaternary ammonium groups described, for example, in French Patent No. 1 492 597, such as the polymers sold under the “JR” names (JR 400, JR 125, JR 30M) or “LR” names (LR 400, LR 30M) by Dow Chemical. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose which has reacted with an epoxide substituted by a trimethylammonium group.
  • Cationic cellulose polymers such as cellulose copolymers and cellulose derivatives grafted with at least one water-soluble quaternary ammonium monomer and described, for example, in Patent US 4 131 576, such as hydroxyalkylcelluloses, for example hydroxymethyl-, hydroxyethyl- and hydroxypropylcelluloses, grafted in particular with at least one group chosen from methacryloyloxyethyltrimethylammonium, methacrylamidopropyltrimethylammonium and dimethyldiallylammonium.
  • the commercial products corresponding to these polymers comprise, for example, the products sold under the names Celquat® L 200 and Celquat® H 100 by Akzo Nobel.
  • Cationic cellulose polymers having at least one quaternary ammonium group comprising at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups comprising at least 8 carbon atoms. It may be preferable for the cationic cellulose polymers to be quaternized hydroxyethylcelluloses modified by at least one quaternary ammonium group comprising at least one fatty chain, such as alkyl, arylalkyl or alkylaryl groups comprising at least 8 carbon atoms, or their mixtures.
  • the alkyl radicals carried by the quaternary ammonium group can preferably contain from 8 to 30 carbon atoms, in particular from 10 to 30 carbon atoms.
  • the aryl radicals preferably denote phenyl, benzyl, naphthyl or anthryl groups. More preferentially, the cationic cellulose polymer can comprise at least one quaternary ammonium group comprising at least one C 8 -C 30 hydrocarbon group.
  • Quatrisoft LM 200 Quatrisoft LM-X 529-18-A,
  • the composition comprises at least one cationic polysaccharide chosen from polyquaternium-4, polyquaternium-10, polyquaternium-24 or polyquaternium-67.
  • the amount of cationic polysaccharides in the composition according to the present invention can be of 0.01% by weight or more, preferably 0.05% by weight or more and more preferably 0.07% by weight or more, with respect to the total weight of the composition.
  • the amount of cationic polysaccharides in the composition according to the present invention can be of 10% by weight or less, preferably 5% by weight or less and more preferably 1% by weight or less, with respect to the total weight of the composition.
  • the amount of cationic polysaccharides in the composition according to the present invention can be from 0.01% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferentially from 0.05% to 1% by weight, better still from 0.07% to 1% by weight, with respect to the total weight of the composition.
  • the composition according to the present invention comprises at least one crosslinking agent chosen from non-polymeric acids having three or more acid groups and their salts. Two or more different types of acids having three or more acid groups and/or their salts can be used in combination. Thus, a single type of acid having three or more acid groups and/or its salts or a combination of different types of acids having three or more acid groups and/or their salts can be used. At least one of the acid groups of each of these acids can be in the form of a salt. All the acid groups of these acids can be in the form of salts.
  • salt in the present invention means a salt formed by addition of one or several appropriate bases to the acid having three or more acid groups, which salt can be obtained from a reaction between the acid having three or several acid groups with the base(s) according to the methods known to a person skilled in the art. Mention may be made, as salt, of metal salts, for example alkali metal, such as Na and K, salts and alkaline earth metal, such as Mg and Ca, salts, and ammonium salts.
  • alkali metal such as Na and K
  • salts and alkaline earth metal such as Mg and Ca
  • salts and ammonium salts.
  • the crosslinking agent(s) are chosen from non-polymeric acids having three or more acid groups, preferably from non-polymeric organic acids having three or more acid groups.
  • non-polymeric means here that the crosslinking agent is a small molecule, which includes oligomers consisting of a small number (usually less than ten) of identical or very similar elements and molecules that are not obtained by polymerization of two or more monomers. Consequently, the non-polymeric acid, in particular the non-polymeric organic acid, does not correspond to an acid obtained by polymerization of a number greater than or equal to 10 monomers, such as polycarboxylic acid.
  • the molecular weight of the non-polymeric acid, in particular of the non-polymeric organic acid, having three or more acid groups is of 1000 or less, preferably 800 or less, more preferably 600 or less, and better 400 or less.
  • the non-polymeric acid(s) having three or more acid groups, or a salt of these, can be hydrophilic or water-soluble.
  • the non-polymeric acid(s) having three or more acid groups can have three or more acid groups chosen from carboxylic, sulfuric, sulfonic, phosphonic, phosphoric or hydroxyphenolic groups, and a mixture of these.
  • the non-polymeric acid(s) having three or more acid groups and their salts can be chosen from tricarboxylic acids, tetracarboxylic acids, pentacarboxylic acids, hexacarboxylic acids, their salts and their mixtures.
  • the non-polymeric acid(s) having three or more acid groups and their salts can be chosen from citric acid, aconitic acid, phytic acid, EDTA, glycyrrhizin, inositol triphosphate, inositol pentakisphosphate, tripolyphosphate, adenosine triphosphate, and their salts.
  • the non-polymeric acid(s) having three or more acid groups and their salts are chosen from citric acid, phytic acid, and their salts.
  • the amount of non-polymeric acids having three or more acid groups and their salts in the composition according to the present invention can be of 0.001% by weight or more, preferably 0.005% by weight or more and more preferentially 0.01% by weight or more, better still 0.1% by weight or more, with respect to the total weight of the composition.
  • the amount of non-polymeric acids having three or more acid groups and their salts in the composition according to the present invention can be of 10% by weight or less, preferably 5% by weight or less and more preferentially 1% by weight or less, with respect to the total weight of the composition.
  • the amount of non-polymeric acids having three acid groups and their salts in the composition according to the present invention can be from 0.001% to 10% by weight, preferably from 0.005% to 5% by weight and more preferentially from 0.01% to 1% by weight, better still from 0.1% to 1% by weight, with respect to the total weight of the composition.
  • composition in accordance with the invention can comprise at least one oily phase.
  • oil phase is understood to mean a phase comprising at least one oil and all of the fat-soluble and lipophilic ingredients and of the fatty substances used for the formulation of the compositions of the invention.
  • oil is understood to mean any fatty substance in the liquid form at ambient temperature (20-25°C) and at atmospheric pressure (760 mmHg).
  • the oily phase can comprise, besides the merocyanine screening agent(s) and optionally the lipophilic additional screening agent(s), at least one volatile or non-volatile hydrocarbon oil and/or one volatile and/or non-volatile silicone oil and/or one volatile and/or non-volatile fluorinated oil.
  • silicon oil is understood to mean an oil comprising at least one silicon atom and in particular at least one Si-O group.
  • hydrocarbon oil is understood to mean an oil mainly containing hydrogen and carbon atoms and optionally one or more heteroatoms, in particular nitrogen and oxygen.
  • these oils can in particular contain one or more carboxyl, ester, ether or hydroxyl functional groups.
  • fluorinated oil is understood to mean an oil comprising at least one fluorine atom.
  • volatile oil is understood to mean an oil which 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).
  • non-volatile hydrocarbon oils which can be used according to the invention, of:
  • hydrocarbon oils of vegetable origin such as glyceride triesters, which are generally triesters of fatty acids and of glycerol, the fatty acids of which can have varied chain lengths from C 4 to C 24 , it being possible for these chains to be saturated or unsaturated and linear or branched; these oils are in particular wheat germ oil, sunflower oil, grape seed oil, sesame oil, maize oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, red kuri squash oil, pumpkin oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil or musk rose oil; or alternatively triglycerides of caprylic/capric acids, such as
  • synthetic esters such as the oils of formula RCOOR' in which R represents the residue of a linear or branched fatty acid comprising from 1 to 40 carbon atoms and R' represents a hydrocarbon chain, in particular branched hydrocarbon chain, containing from 1 to 40 carbon atoms, with the proviso that R + R' ⁇ 10, such as, for example, Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C 12 -C 15 alkyl benzoates, such as the product sold under the trade name Finsolv TN® or Witconol TN® by Witco or Tegosoft TN® by Evonik Goldschmidt, 2-ethylphenyl benzoate, such as the commercial product sold under the name X-Tend 226® by ISP, isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl is
  • fatty alcohols which are liquid at ambient temperature, comprising a branched and/or unsaturated carbon-based chain having from 12 to 26 carbon atoms, such as octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol or 2-undecylpentadecanol;
  • higher C 12 -C 22 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 Cognis;
  • non-volatile hydrocarbon oils which can be used according to the invention, to glyceride triesters and in particular triglycerides of caprylic/capric acids, synthetic esters and in particular isononyl isononanoate, oleyl erucate, C 12 -C 15 alkyl benzoates or 2-ethylphenyl benzoate, and fatty alcohols, in particular octyldodecanol.
  • volatile hydrocarbon oils which can be used according to the invention, of hydrocarbon oils having from 8 to 16 carbon atoms and in particular of branched C 8 -C 16 alkanes, such as C 8 -C 16 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 C 8 -C 16 esters, isohexyl neopentanoate, and their mixtures.
  • hydrocarbon oils having from 8 to 16 carbon atoms and in particular of branched C 8 -C 16 alkanes, such as C 8 -C 16 isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane or
  • n-dodecane C 12
  • n-tetradecane C 14
  • Sasol n-dodecane sold by Sasol respectively under the references Parafol 12-97 and Parafol 14-97®, and also their mixtures.
  • volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the name Shell Solt® by Shell, can also be used.
  • the volatile solvent is chosen from volatile hydrocarbon oils having from 8 to 16 carbon atoms, and their mixtures.
  • the non-volatile silicone oils can be chosen in particular from non-volatile polydimethylsiloxanes (PDMSs), polydimethylsiloxanes comprising alkyl or alkoxy groups, which groups are pendent and/or at the end of the silicone chain and each have from 2 to 24 carbon atoms, or phenylated silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphenyl dimethicones, diphenyl(methyldiphenyl)trisiloxanes or (2-phenylethyl)trimethylsiloxysilicates.
  • PDMSs non-volatile polydimethylsiloxanes
  • phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphen
  • volatile silicone oils for example, of volatile linear or cyclic silicone oils, in particular those having a viscosity ⁇ 8 centistokes (8 ⁇ 10 -6 m 2 /s) and having in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms.
  • volatile silicone oils which can be used in the invention, of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and their mixtures.
  • R represents an alkyl group comprising from 2 to 4 carbon atoms and one or more hydrogen atoms of which can be replaced by a fluorine or chlorine atom.
  • Use may also be made of volatile fluorinated oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane and their mixtures.
  • volatile fluorinated oils such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane and their mixtures.
  • An oily phase according to the invention can additionally comprise other fatty substances, mixed with or dissolved in the oil.
  • Another fatty substance which can be present in the oily phase can, for example, be:
  • waxes such as lanolin, beeswax, carnauba or candelilla wax, paraffin waxes, lignite waxes, microcrystalline waxes, ceresin or ozokerite, or synthetic waxes, such as polyethylene waxes or Fischer-Tropsch waxes;
  • a pasty compound such as polymeric or non-polymeric silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives;
  • the overall oily phase including all the lipophilic substances 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, with respect to the total weight of the composition.
  • composition in accordance with the invention can additionally comprise at least one aqueous phase.
  • the aqueous phase contains water and optionally other water-soluble or water-miscible organic solvents.
  • An aqueous phase which is suitable for the invention can 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 water-soluble or water-miscible solvents which are suitable for the invention comprise short-chain monoalcohols, for example C 1 -C 4 monoalcohols, such as ethanol or isopropanol; diols or polyols, such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, glycerol and sorbitol, and their mixtures.
  • monoalcohols for example C 1 -C 4 monoalcohols, such as ethanol or isopropanol
  • diols or polyols such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene
  • use may more particularly be made of ethanol, propylene glycol, glycerol and their mixtures.
  • the overall aqueous phase including all the hydrophilic substances 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, with respect to the total weight of the composition.
  • compositions according to the invention can additionally contain one or more additional UV-screening agents, other than the merocyanine derivatives and triazine derivatives as described above, chosen from hydrophilic, lipophilic or insoluble organic UV-screening agents and/or one or more inorganic pigments. It will preferentially be constituted of at least one hydrophilic, lipophilic or insoluble organic UV-screening agent.
  • hydrophilic UV-screening agent is understood to mean any cosmetic or dermatological, organic or inorganic, compound which screens out UV radiation and which is capable of being completely dissolved in the molecular state in a liquid aqueous phase or else of being dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
  • lipophilic screening agent is understood to mean any cosmetic or dermatological, organic or inorganic, compound which screens out UV radiation and which is capable of being completely dissolved in the molecular state in a liquid fatty phase or else of being dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.
  • insoluble UV-screening agent is understood to mean any cosmetic or dermatological, organic or inorganic, compound which screens out UV radiation and 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 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 can be easily evaluated in the laboratory.
  • the additional organic UV-screening agents are chosen in particular from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidenecamphor compounds; benzophenone compounds; ⁇ , ⁇ -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, such as described in Patents EP 669 323 and US 2 463 264; methylenebis(hydroxyphenylbenzotriazole) compounds, such as described in Applications US 5 237 071, US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 119; benzoxazole compounds, such as described in Patent Applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening polymers and screening silicones, such as
  • Cinnamic compounds are 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.
  • Butyl Methoxydibenzoylmethane sold in particular under the trade name Parsol ® 1789 by DSM Nutritional Products.
  • Ethylhexyl Salicylate sold under the name Neo Heliopan ® OS by Symrise.
  • Octocrylene sold in particular under the trade name Uvinul ® N 539 T by BASF.
  • Benzophenone-3 or Oxybenzone sold under the trade name Uvinul ® M 40 by BASF,
  • 1,1'-(1,4-Piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]methanone] (CAS 919803-06-8), as described in Application WO2007/071584; this compound advantageously being used in micronized form (mean size of 0.02 to 2 ⁇ m), which can be obtained, for example, according to the micronization process described in Applications GB-A-2 303 549 and EP-A-893 119, and in particular in the form of an aqueous dispersion.
  • Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name Eusolex ® 232 by Merck.
  • Drometrizole Trisiloxane manufactured under the name Mexoryl® XL by Noveal.
  • 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
  • aqueous dispersion of micronized particles having a mean particle size which varies from 0.01 to 5 ⁇ m, more preferentially from 0.01 to 2 ⁇ m and more particularly from 0.020 to 2 ⁇ m, with at least one alkylpolyglycoside surfactant having the structure C n H 2n+1 O(C 6 H 10 O 5 ) x H, in which n is an integer from 8 to 16 and x is the mean degree of polymerization of the (C 6 H 10 O 5 ) unit and varies from 1.4 to 1.6, such as described in Patent GB-A-2 303 549, sold in particular under the trade name Tinosorb ® M by BASF, or
  • aqueous dispersion of micronized particles having a mean particle size which varies from 0.02 to 2 ⁇ m, more preferentially from 0.01 to 1.5 ⁇ m and more particularly from 0.02 to 1 ⁇ m, in the presence of at least one polyglyceryl mono(C 8 -C 20 )alkyl ester having a degree of glycerol polymerization of at least 5, such as the aqueous dispersions described in Application WO2009/063392, in particular the product sold under the name Tinosorb WPGL by BASF.
  • Neo Heliopan ® MA Menthyl Anthranilate, sold under the trade name Neo Heliopan ® MA by Symrise.
  • Polyorganosiloxane comprising benzalmalonate functional groups such as Polysilicone-15, sold under the trade name Parsol SLX® by Hoffmann-La Roche.
  • the screening agent with the INCI name 2,2'-(1,4-Phenylene)bis(1,3-benzoxazole offered under the name DBO by DSM.
  • 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 having a mean elementary particle size of less than or equal to 0.5 ⁇ m, more preferentially of between 0.005 and 0.5 ⁇ m, more preferentially still of between 0.01 and 0.2 ⁇ m, better still between 0.01 and 0.1 ⁇ m and more particularly between 0.015 and 0.05 ⁇ m. They are described in particular in annexe VI updated on 22/03/2021 of the European regulation on cosmetic products number 1223/2009, but are not limited to this list.
  • They can be chosen in particular from titanium oxide, zinc oxide, iron oxide, zirconium oxide, cerium oxide or their mixtures.
  • Such coated or non-coated metal oxide pigments are described in particular in Patent Application EP-A-0 518 773. Mention may be made, as commercial pigments, of the products sold by Croda, Tayca and Merck.
  • the metal oxide pigments can be coated or non-coated.
  • the coated pigments are pigments which 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.
  • coated pigments are more particularly titanium oxides coated:
  • silica and alumina such as the products MT-500SA ® and MT-100SA ® from Tayca and TioveilTM AQ-N from Croda,
  • alumina and aluminium stearate such as the products MT-100TV ® , MT-100Z ® and MT-01 ® from Tayca, the product SolaveilTM CT100 from Croda and the product Eusolex T-AVO ® from Merck,
  • 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 can additionally comprise one or more dispersing agents, such as, for example, a sorbitan ester, such as sorbitan isostearate, a polyoxyalkylenated glycerol fatty acid ester, such as Tri-PPG-3 Myristyl Ether Citrate and Polyglyceryl-3 Polyricinoleate.
  • the oily dispersion of titanium oxide particles comprises at least one dispersing agent chosen from polyoxyalkylenated glycerol fatty acid esters.
  • the non-coated titanium oxide pigments are sold, for example, by Tayca under the trade names MT-500B or MT-600B ® , by Evonik under the name Degussa P 25.
  • the non-coated zinc oxide pigments are, for example:
  • NanoArc® Zinc Oxide sold under the name NanoArc® Zinc Oxide by Nanophase Technologies.
  • coated zinc oxide pigments are, for example:
  • the non-coated cerium oxide pigments can, for example, be those sold under the name Rhodigard ® W185 by Solvay.
  • coated or non-coated 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 at a content ranging from 0.1% to 60% by weight and in particular from 5% to 30% by weight, with respect to the total weight of the composition.
  • composition in accordance with the present invention can additionally comprise conventional cosmetic adjuvants chosen in particular from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoaming agents, fragrances, preservatives, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, basifying or acidifying agents or any other ingredient generally 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, antifoaming agents, fragrances, preservatives, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propel
  • alcohols other than C 1 -C 4 monoalkanols as defined above and in particular short-chain C 2 -C 8 polyols such as glycerol, diols, such as caprylyl glycol, 1,2-pentanediol, propanediol or butanediol, glycols and glycol ethers, such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol
  • carboxyvinyl polymers such as the Carbopols ® (Carbomers) and the Pemulens, such as Pemulen TR1 ® and Pemulen TR2 ® (Acrylates/C10-C30 Alkyl Acrylate Crosspolymer); polyacrylamides, such as, for example, the crosslinked copolymers sold under the names Sepigel 305 ® (CTFA name: Polyacrylamide/C13-14 Isoparaffin/Laureth-7) or Simulgel 600 (CTFA name: Acrylamide/Sodium Acryloyldimethyl Taurate Copolymer/Isohexadecane/Polysorbate 80) by SEPPIC; 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers which are optionally crosslinked and/or neutralized, such as the poly(2-acrylamido-2-methylpropanesulfonic acid) sold by Hoechst under the trade name Hostacerin AMP
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, or sulfonic acids.
  • basifying agents by way of example, of aqueous ammonia, alkali metal carbonates, alkanolamines, such as mono-, di- and triethanolamines and their derivatives, sodium hydroxide or potassium hydroxide.
  • the cosmetic composition comprises one or more basifying agents chosen from alkanolamines, in particular triethanolamine, and sodium hydroxide.
  • the pH of the composition in accordance with the invention is generally of between 3 and 12 approximately, preferably between 5 and 11 approximately and more particularly still from 5.5 to 8.
  • said active agent(s) as a function of the effect desired on the skin, the hair, the eyelashes, the eyebrows or the nails.
  • compositions according to the invention can be prepared according to the techniques well known to a person skilled in the art. They can be provided in particular in the form of a simple or complex (O/W, W/O, O/W/O or W/O/W) emulsion, such as a cream, a milk or a gel-cream.
  • a simple or complex (O/W, W/O, O/W/O or W/O/W) emulsion such as a cream, a milk or a gel-cream.
  • anhydrous composition is understood to mean a composition containing less than 1% by weight of water, indeed even less than 0.5% of water, and in particular devoid of water, the water not being added during the preparation of the composition but corresponding to the residual water contributed by the mixed ingredients.
  • compositions in accordance with the invention can also be provided in the aqueous form, with an amount of oily phase preferably of less than 1% by weight, more preferentially still of less than 0.5% by weight, and in particular devoid of oily phase.
  • They can optionally be packaged as an aerosol and be provided in the form of a foam or of a spray.
  • compositions in the form of oil-in-water or water-in-oil emulsions in the case of oil-in-water or water-in-oil emulsions, the emulsification processes which can be used are of the paddle or propeller, 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 appropriately chosen according to the emulsion to be obtained (W/O or O/W).
  • W/O emulsifying surfactants of alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars; or silicone surfactants, such as dimethicone copolyols, for example the mixture of cyclomethicone and dimethicone copolyol sold under the name DC 5225 C ® by Dow Corning, and alkyl dimethicone copolyols, such as lauryl methicone copolyol, sold under the name Dow Corning 5200 Formulation Aid by Dow Corning, or cetyl dimethicone copolyol, such as the product sold under the name Abil EM 90R ® by Goldschmidt and the mixture of cetyl dimethicone copolyol, polyglyceryl isostearate (4 mol) and hexyl laurate sold under the name Abil WE O9 ® by Goldschmidt. It is also possible
  • non-silicone emulsifying surfactants in particular alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars.
  • polyol alkyl esters of polyethylene glycol esters, such as PEG-30 Dipolyhydroxystearate, such as the product sold under the name Arlacel P135 ® by ICI.
  • glycerol and/or sorbitan esters for example, of polyglyceryl isostearate, such as the product sold under the name Isolan GI 34 ® by Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 ® by ICI; sorbitan isostearate and glyceryl isostearate, such as the product sold under the name Arlacel 986 ® by ICI, and their mixtures.
  • polyglyceryl isostearate such as the product sold under the name Isolan GI 34 ® by Goldschmidt
  • sorbitan isostearate such as the product sold under the name Arlacel 987 ® by ICI
  • sorbitan isostearate and glyceryl isostearate such as the product sold under the name Arlacel 986 ® by ICI, and their mixtures.
  • O/W emulsions for example, as non-ionic emulsifying surfactants, of 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 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
  • the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol can be in the form of a self-emulsifying composition, as described, for example, in the document WO-A-92/06778.
  • the aqueous phase of the latter can 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 have applications in a large number of treatments, in particular cosmetic treatments, of the skin, lips and hair, including the scalp, in particular for protecting and/or caring for the skin, lips and/or hair and/or for making up the skin and/or lips.
  • compositions according to the invention as defined above in the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and/or scalp, in particular of care products, sun protection products and make-up products.
  • the cosmetic compositions according to the invention can be used, for example, as make-up products.
  • Another subject-matter of the present invention is constituted of a non-therapeutic cosmetic method 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.
  • the cosmetic compositions according to the invention can, for example, be used as care products and/or sun protection products for the face and/or body with a liquid to semi-liquid consistency, such as milks, more or less smooth creams, gel-creams or pastes. They can optionally be packaged as an aerosol and be provided in the form of a foam or of 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 a person 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 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, with respect to the total weight of the composition.
  • propellants such as, for example, hydrofluorinated compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane.
  • the invention also relates to a cosmetic assembly comprising:
  • a container delimiting one or more compartment(s), said container being closed by a closing member and optionally being unsealed;
  • the container can, for example, be in the form of a pot or a case.
  • the closing member can 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 make-up and/or care composition(s).
  • composition ingredients are given as % by weight, with respect to the total weight of the composition.
  • Example Base Solvent Example A1.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide
  • Example A1.2 triethylamine isopropanol
  • Example A1.3 3-methoxypropylamine isopropanol
  • Example A1.4 3-methoxypropylamine tert-amyl alcohol
  • Example A1.5 3-methoxypropylamine toluene
  • the completion of the alkylation reaction can be monitored, for example by methods such as TLC, GC or HPLC.
  • Example Base Solvent Example A2.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide
  • Example A2.2 triethylamine isopropanol
  • Example A2.3 3-methoxypropylamine isopropanol
  • Example A2.4 3-methoxypropylamine tert-amyl alcohol
  • Example A2.5 3-methoxypropylamine toluene
  • the crude product (15) is obtained in the form of a dark brown oil.
  • Example Base Solvent Example A3.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide
  • Example A3.2 triethylamine isopropanol
  • Example A3.3 3-methoxypropylamine isopropanol
  • Example A3.4 N-methylmorpholine tert-amyl alcohol
  • Example A3.5 3-methoxypropylamine toluene
  • Example A3.6 3-methoxypropylamine dimethylformamide
  • Example Base Solvent Example A4.1 DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide
  • Example A4.2 triethylamine isopropanol
  • Example A4.3 3-methoxypropylamine isopropanol
  • Example A4.4 N-methylmorpholine tert-amyl alcohol
  • Example A4.5 3-methoxypropylamine toluene
  • the aqueous phase A1 is prepared by mixing all the starting materials while heating at 80°C until a homogeneous phase is obtained.
  • the phase A2 is added to the phase A1 when the temperature has returned to 25°C.
  • the phase B2 is introduced with stirring into the phase B1, preheated to 50°C, until a homogeneous phase is obtained.
  • the phase B is prepared by mixing all the ingredients while heating at 50°C, until a homogeneous phase is obtained.
  • the emulsion is prepared by introduction of the phase B into the phase A with vigorous stirring for 10 minutes at 25°C.
  • the phase C is subsequently introduced, then the phase D and finally the phase E with stirring until a smooth formula is obtained.
  • the product is transferred onto a white cotton fabric by means of a 25 cm2 PMMA sheet.
  • the amount deposited is equivalent to 2 mg/cm2.
  • the fabric is subsequently left to dry in the open air for 24 h, then machine washed (Colour 40°C programme – duration 1 h 30) with a liquid detergent.
  • the staining capacity is evaluated 24 hours and 3 weeks after washing via the measurement of the ⁇ E obtained by means of a chromameter (Konica Minolta Sensing Europe BV).
  • the ⁇ E which measures the total colour variation between an area stained by the formula and an unstained area of the washed and then dried fabric, and after having waited a moment t after the machine washing. The lower the ⁇ E, the weaker the staining of the fabrics by the product.
  • ⁇ E is calculated from the variations ⁇ L, ⁇ a and ⁇ b according to the following formula:
  • ⁇ L represents the difference between the value of L of the unstained area and the value of L of the stained area after a moment t after the washing of the fabric
  • ⁇ a represents the difference between the value of a of the unstained area and the value of a of the stained area after a moment t after the washing of the fabric
  • ⁇ b represents the difference between the value of b of the unstained area and the value of b of the stained area after a moment t after the washing of the fabric.
  • compositions 1 to 4 were prepared according to the protocol described in detail above.
  • Phase Ingredients 1 (reference) 2 (invention) A1 Butyl Methoxydibenzoylmethane 0 0 A1 Diethylamino Hydroxybenzoyl Hexyl Benzoate 0 0 A1 Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate 0 3
  • A1 Triethyl Citrate 8 8 A1 C15-19 Alkane q.s. for 100 q.s.
  • Alcohol 8 8 Phase Ingredients 3 (comparative) 4 (comparative) A1 Butyl Methoxydibenzoylmethane 3 0 A1 Diethylamino Hydroxybenzoyl Hexyl Benzoate 0 3 A1 Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate 0 0 A1 Diisopropyl Sebacate 5 5 A1 Dicaprylyl Carbonate 5 5 A1 Triethyl Citrate 8 8 A1 C15-19 Alkane q.s. for 100 q.s.
  • composition 2 in which Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate (compound 25) is used as UVA-screening agent, leaves marks after washing (after 24 h and after 3 weeks) which are equivalent to those left by the reference composition 1 which does not contain UVA-screening agents.
  • the composition 2 leaves fewer marks after washing than the comparative compositions 3 and 4, in which Butyl Methoxydibenzoylmethane (for example Parsol 1789 from DSM) or Diethylamino Hydroxybenzoyl Hexyl Benzoate (for example Uvinul A+ from BASF) is used as UVA-screening agent.
  • Butyl Methoxydibenzoylmethane for example Parsol 1789 from DSM
  • Diethylamino Hydroxybenzoyl Hexyl Benzoate for example Uvinul A+ from BASF

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Abstract

La présente invention concerne une composition cosmétique ou dermatologique comprenant : a) au moins une mérocyanine représentée par la formule (3) suivante : (3), et b) au moins un complexe polyionique contenant au moins un polysaccharide cationique et au moins un agent de réticulation choisi parmi les acides non polymères ayant au moins trois valeurs pKa et leurs sels.
PCT/EP2023/053301 2022-02-15 2023-02-10 Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique WO2023156298A1 (fr)

Applications Claiming Priority (2)

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FRFR2201329 2022-02-15
FR2201329A FR3132637A1 (fr) 2022-02-15 2022-02-15 Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique

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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
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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
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EP0832642A2 (fr) 1996-09-13 1998-04-01 3V SIGMA S.p.A Dérivés de benzoxazole et utilisation comme filtres ultraviolet
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
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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
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
WO2006035000A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion photoprotectrice a teneur elevee en pigments filtrants, photoprotecteurs
WO2006034992A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion cosmetique de protection solaire contenant des micropigments organiques
WO2006035007A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Preparation cosmetique de protection solaire a base de micropigments
WO2006034991A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion eau dans l'huile contenant des pigments filtrants de protection solaire anti-uv
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
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
WO2013153678A1 (fr) 2012-04-11 2013-10-17 L'oreal Feuille cosmétique autoportante
FR3001216A1 (fr) * 2013-01-21 2014-07-25 Oreal Composition cosmetique ou dermatologique comprenant une merocyanine, une phase huileuse et un mono-alcanol en c1-c4
JP2014227389A (ja) 2013-05-24 2014-12-08 ロレアル 自立性美容シート
US20210177725A1 (en) * 2018-08-30 2021-06-17 L'oreal Self-healing or self-repairing film forming composition

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FR1492597A (fr) 1965-09-14 1967-08-18 Union Carbide Corp Nouveaux éthers cellulosiques contenant de l'azote quaternaire
FR2315991A1 (fr) 1975-06-30 1977-01-28 Oreal Procede de fabrication de dispersions aqueuses de spherules lipidiques et nouvelles compositions correspondantes
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US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2416008A1 (fr) 1978-02-02 1979-08-31 Oreal Lyophilisats de liposomes
EP0133981A2 (fr) 1983-08-05 1985-03-13 Siemens Aktiengesellschaft Protection mécanique contre les surcharges
US4749643A (en) 1985-09-03 1988-06-07 Agfa Gevaert Aktiengesellschaft Photographic recording element containing a UV absorbent and a silver halide emulsion layer
US4850517A (en) 1985-09-27 1989-07-25 Airspray International B.V. Pressurized spray dispenser having valved mixing chamber
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
WO1992006778A1 (fr) 1990-10-17 1992-04-30 Societe D'exploitation De Produits Pour Les Industries Chimiques (S.E.P.P.I.C.) Utilisation de compositions a base d'alcools gras, pour la preparation d'emulsions; procede de preparation d'emulsions et emulsions ainsi obtenues
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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
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
EP0832642A2 (fr) 1996-09-13 1998-04-01 3V SIGMA S.p.A Dérivés de benzoxazole et utilisation comme filtres ultraviolet
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
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
WO2006035000A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion photoprotectrice a teneur elevee en pigments filtrants, photoprotecteurs
WO2006034992A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion cosmetique de protection solaire contenant des micropigments organiques
WO2006035007A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Preparation cosmetique de protection solaire a base de micropigments
WO2006034991A1 (fr) 2004-09-27 2006-04-06 Beiersdorf Ag Emulsion eau dans l'huile contenant des pigments filtrants de protection solaire anti-uv
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
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
WO2013153678A1 (fr) 2012-04-11 2013-10-17 L'oreal Feuille cosmétique autoportante
FR3001216A1 (fr) * 2013-01-21 2014-07-25 Oreal Composition cosmetique ou dermatologique comprenant une merocyanine, une phase huileuse et un mono-alcanol en c1-c4
JP2014227389A (ja) 2013-05-24 2014-12-08 ロレアル 自立性美容シート
US20210177725A1 (en) * 2018-08-30 2021-06-17 L'oreal Self-healing or self-repairing film forming composition

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