Cosmetic or dermatological composition comprising a merocyanin and di-t-butyl pentaerythrityl tetrahydroxycinnamate

Abstract

Cosmetic or dermatological composition comprising a merocyanin and di-t-butyl pentaerythrityl tetrahydroxycinnamate. The present invention relates to a composition, in particular a cosmetic or dermatological composition, comprising: a) at least one merocyanin corresponding to the following formula (3), as well as their isomeric geometric forms, in particular E / E or E / Z: [Formula 3] in which: A is –O- or –NH; R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alcinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups being able to be interrupted by one or more O's; and b) di-t-butyl pentaerythrityl tetrahydroxycinnamate. The present invention also relates to a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition as defined above.

Description

Title of the invention: Cosmetic or dermatological composition comprising a merocyanine and di-t-butyl pentaerythrityl tetrahydroxycinnamate

[0001] The present invention relates to a cosmetic or dermatological composition comprising at least one merocyanin of formula (3) which will be defined in detail later and di-t-butyl pentaerythrityl tetrahydroxycinnamate.

[0002] The present invention also relates to a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition according to the invention as defined above.

[0003] It also relates to a non-therapeutic cosmetic process for limiting skin darkening and / or improving the color and / or homogeneity of the complexion comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0004] It also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratinous material comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0005] It is known that radiation with wavelengths between 280 nm and 400 nm allows the human epidermis to tan, and that radiation with wavelengths between 280 and 320 nm, known as UV-B rays, interferes with the development of a natural tan. Exposure is also likely to induce an alteration of the biomechanical properties of the epidermis, resulting in the appearance of wrinkles and leading to premature skin aging.

[0006] It is also known that UV-A rays with wavelengths between 320 and 400 nm penetrate the skin more deeply than UV-B rays. UV-A rays cause immediate and persistent tanning of the skin. Daily exposure to UVA rays, even for short periods, under normal conditions can lead to the degradation of collagen and elastin fibers, resulting in changes to the skin's microrelief, the appearance of wrinkles, and uneven pigmentation (brown spots, uneven skin tone).

[0007] Protection against UVA and UVB radiation is therefore necessary. An effective photoprotection product must protect against both UVA and UVB radiation.

[0008] Numerous photoprotective compositions have been proposed to date for These products are designed to counteract the effects of UVA and / or UVB radiation. They typically contain organic and / or inorganic UV filters that function according to their chemical nature and properties by absorbing, reflecting, or scattering UV radiation. They generally contain mixtures of oil-soluble organic filters and / or water-soluble UV filters combined with metal oxide pigments such as titanium dioxide or zinc oxide.

[0009] Numerous cosmetic compositions designed to limit skin darkening and improve skin tone and evenness have been proposed to date. It is well known in the field of sunscreens that such compositions can be obtained using UV filters, and in particular UVB filters. Some compositions may also contain UVA filters. This filtering system must provide UVB protection in order to limit and control the neosynthesis of melanin that promotes overall pigmentation, but it must also provide UVA protection in order to limit and control the oxidation of existing melanin that leads to skin darkening.

[0010] However, it is extremely difficult to find a composition containing a particular combination of UV filters that would be specially adapted for the photoprotection of the skin and particularly for an improvement in the quality of the skin both in terms of color and its mechanical properties of elasticity.

[0011] Advantageously, this improvement is particularly sought on already pigmented skin in order not to increase either the pigment load in melanin or the structure of the melanin already present in the skin.

[0012] In fact, the majority of organic UV filters consist of aromatic compounds absorbing in the wavelength range between 280 and 370 nm. In addition to their ability to filter solar radiation, the desired photoprotective compounds must also exhibit good cosmetic properties, good solubility in common solvents, particularly in fatty substances such as oils or in water, as well as good photostability, either alone or in combination with other UV filters. They must also be colorless or at least have a color that is cosmetically acceptable to the consumer.

[0013] One of the main drawbacks known to date of these compositions is that these filtering systems have insufficient effectiveness against UV radiation and particularly against long UVA radiation with wavelengths beyond 370 nm in order to control photo-induced pigmentation and its evolution by a UV filtering system over the entire UV spectrum.

[0014] Among all the compounds that have been recommended for this effect, an interesting family of UV filters has been proposed, consisting of derivatives of carbon merocyanine. which is described in patent US4195999, application WO2004 / 006878 and document IP COM Journal 4 (4), 16 No. IPCOM000011179D published on 04 / 03 / 2004. These compounds exhibit very good filtration properties in long UVA radiation but have only slightly satisfactory solubility in common solvents, both in aqueous and oily phases, and unsatisfactory photostability for some merocyanines.

[0015] In order to find other merocyanins with better solubility in common solvents and better photostability, application WO2013 / 011094 proposed merocyanins comprising polar groups consisting of hydroxyl and ether functions that show good filtration efficiency of long UVA rays. However, the photostability of these particular merocyanins is not yet fully satisfactory, whether used alone or in combination with other filters.

[0016] There therefore remains a need to improve the photostability of these merocyanins in photoprotective formulations, whether these are solubilized in aqueous phase and / or in oil phase, while obtaining good cosmetic properties.

[0017] The Applicant made a surprising discovery that, by using di-t-butyl pentaerythrityl tetrahydroxycinnamate, it was possible to significantly improve the photostability of these merocyanins in both aqueous and oily phases. This discovery forms the basis of the present invention.

[0018] Thus, in accordance with one of the objects of the present invention, a cosmetic or dermatological composition is now proposed comprising at least one me-rocyanin of formula (3) which will be defined in detail later and di-t-butyl pentaerythrityl tetrahydroxycinnamate.

[0019] Furthermore, there is also a need to improve the photostability of merocyanins in the presence of organic filters such as, for example, dibenzoylmethane derivatives. Indeed, the addition of additional filters, particularly dibenzoylmethane derivatives, can destabilize compositions containing a merocyanin.

[0020] Dibenzoylmethane derivatives, and in particular 4-ter-butyl-4'-methoxydibenzoyl methane, constitute a family of particularly effective UV-A filters that exhibit a high intrinsic absorption capacity. These dibenzoylmethane derivatives, which are now well-known products in their own right as active UV-A filters, are described in particular in French patent applications FR-A-2326405 and FR-A-2440933, as well as in European patent application EP-A-0114607; 4-ter-butyl-4'-methoxydibenzoyl methane is also currently offered for sale under the trade name "PARSOL 1789 ®" by DSM NUTRITIONAL PRODUCTS.

[0021] However, it has been observed that combinations of merocyanine derivatives with dibenzoylmethane derivatives have the disadvantage of being particularly photosensitive These particular combinations of UV filters are unstable under ultraviolet radiation (especially UV-A). They degrade more or less rapidly under the action of UV radiation; this degradation is particularly significant for merocyanine derivatives. Thus, this substantial lack of photochemical stability of the combination of merocyanine derivatives with dibenzoylmethane derivatives in the face of the ultraviolet radiation to which this combination is inherently subjected prevents guaranteeing constant protection during prolonged sun exposure. Therefore, repeated applications at regular and frequent intervals must be performed by the user to obtain effective and lasting protection of the skin against UV rays.

[0022] There is therefore also a real need to photostabilize the association of merocyanine derivatives with dibenzoylmethane derivatives against UV radiation, in order to guarantee constant protection during prolonged sun exposure against UV-A radiation.

[0023] The Applicant has surprisingly discovered that by using di-t-butyl pentaerythrityl tetrahydroxinnamate, it was possible to substantially improve the photostability of these merocyanins in an aqueous phase or in an oily phase even in the presence of additional organic UV filters, including dibenzoylmethane derivatives.

[0024] The Applicant also discovered that the use of di-t-butyl pentaerythrityl tetrahydroxycinnamate made it possible to obtain good cosmeticity of the composition comprising the merocyanins, the latter being in particular non-greasy and non-sticky.

[0025] The present invention also relates to a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material comprising the application on the surface of said keratinous material of at least one composition according to the invention as defined above.

[0026] It also relates to a non-therapeutic cosmetic process for limiting skin darkening and / or improving the color and / or homogeneity of the complexion comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0027] It also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratinous material comprising the application on the surface of the keratinous material of at least one composition as defined above.

[0028] The present invention also relates to the use of di-t-butyl pentaerythrityl tetrahydroxycinnamate for photostabilizing a merocyanin of formula (3) as defined below, alone or in the presence of an additional filter, particularly in presence of one or more dibenzoyl methane derivatives such as 4-ter-butyl-4'-methoxydibenzoyl methane.

[0029] Other features, aspects and advantages of the invention will become apparent from the detailed description that follows.

[0030] The composition according to the invention is intended for topical application and therefore contains a physiologically acceptable medium. Hereinafter, "physiologically acceptable medium" means a medium compatible with keratinous materials.

[0031] In the context of the present invention, "keratinic material" means in particular the skin, the scalp, keratinic fibers such as eyelashes, eyebrows, hair, and body hair, nails, mucous membranes such as lips, and more particularly the skin and mucous membranes (body, face, eye contour, eyelids, lips, preferably body, face and lips).

[0032] In what follows, and unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ...".

[0033] Furthermore, the expressions "at least one" and "at least" used in this description are respectively equivalent to the expressions "one or more" and "greater than or equal to".

[0034] By "prevent" or "prevention", according to the invention, means reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of aging of a keratinous material.

[0035] By the expressions "optionally substituted" and "substituted or unsubstituted", it is understood that the radical or group may optionally be substituted by one or more hydroxy; amino group -NR1R2, such that RI and R2 represent, independently of each other, hydrogen atoms or C1-C3 alkyl radicals; carboxylic group -COOH, carbonyl, or C1-C4 alkyl. MEROCYANIS

[0036] According to the present invention, a family of merocyanins corresponding to the following formula (3) and their isomeric geometric forms, in particular E / E- or E / Z-, will be used: [Formula 3] in which: O.^AR A is -O- or -NH; R is an alkyl group at C1-C22, an alkenyl group at C2-C22, a alcinyl group at C2-C22, a cycloalkyl group at C3-C22 or a cycloalkenyl group at C3-C22, said groups being able to be interrupted by one or more O.

[0037] The merocyanine compounds of the invention can be in their isomeric geometric forms E / E-, E / Z-: [formula 3]

[0038] The compounds of formula (3) that are even more preferred are those where: A is -O- ; R is an alkyl in CrC22, which can be interrupted by one or more O's.

[0039] Among the compounds of formula (3), particular use will be made of those chosen from the following group and their isomeric geometric forms, in particular E / E-, E / Z-: [Tables 1] 14 H I [ J ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate 15 £ H ,O CU,M. xx Xk (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylide ne}ethanamide 25 H X ~ 0 A / X / r j a 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate 27 Ov Cx A. Jx 1 h r Kx H %. I" ( 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)ammo]cycl ohex-2-en-1 -ylidene} ethanoate 29 (L Ox-Ox.-^-^xx^^ H 1 0 r 1 'A ■< 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate 31 ] H 1 L J 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate 37 1 H ] " 1 r l 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate

[0040]

[0041] According to a more particularly preferred embodiment of the invention, the compound 2-ethoxyethyl will be used. (2Z)-cyano{ 3-[(3-methoxypropyl)-amino]cyclohex-2-en-l-ylidene]ethanoate (25) in its geometric configuration E / E and / or E / Z. The E / Z form has the following structure: [formula 25]

[0042] The E / E form has the following structure: [formula 25bis]

[0043] The filtering merocyanins according to the invention can be present in the compositions according to the invention in a concentration ranging from 0.1% to 15% by weight, and preferably from 0.2% to 10% by weight and even better from 0.5% to 5% by weight relative to the total weight of the composition.

[0044] The compounds of formula (3), which form a carbocyclic ring containing 6 carbon atoms, 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 heading “Process for producing 3-amino-2-cyclohexan-l-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.

[0045] In particular, compounds of formula (3), such as the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en-l-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, entitled “A cyclic me-rocyanine UV-A absorber: mechanism of formation and crystal structure”, and shown below, for compounds of formula (3): [formula 4] And more specifically for compound 25 described in Table 1: [Formula 5] DI-T-BUTYL PENTAERYTHRITYL TETRA HYDROXYCINNAMATE

[0046] The composition according to the invention comprises di-t-butyl pentaerythrityl tetrahydroxycinnamate.

[0047] Di-t-butyl pentaerythrityl tetrahydroxycinnamate or tetra-di-t-butyl hydroxyhydrocinnamate pentaerythrityl is a compound, which is part of the family of cinnamic acids and their derivatives, whose CAS number is 6683-19-8.

[0048] By way of example, one can cite the di-t-butyl pentaerythrityl tetrahydroxycinnamate compound marketed by BASF under the name Tinogard TT ®

[0049] Preferably, 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 preferably from 0.1% to 0.3% by weight of di-t-butyl pentaerythrityl tetrahydroxycinnamate compound, relative to the total weight of the composition. COMPOUNDS DERIVED FROM DIBENZOYLMETHANE

[0050] According to a particular embodiment, the composition according to the present invention further comprises one or more dibenzoylmethane derivatives selected from those of the following formula and / or mixtures thereof: [Formula 6] in which: RI, R4, R5 and R6 represent, independently of each other, a hydrogen atom; a hydroxyl 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 each other, a hydrogen atom; a hydroxy radical; an alkyl radical, linear or branched, in C1-C4; an alkoxy radical, linear or branched, in C1-C4; or form with the 2 carbon atoms covalent bonds C-R2 and C-R3 a heterocycle with 5 or 6 links possibly substituted by a hydrocarbon chain, linear or branched, in C1-C4.

[0051] When R2 and R3 form a heterocycle with the 2 carbon atoms of the covalent bonds C-R2 and C-R3, preferably they form a 5-membered aromatic heterocycle, more preferably a furan ring.

[0052] Preferably, R2 and R3 represent, independently of each other, a hydrogen atom; a hydroxy radical; a linear or branched alkyl radical, in C1-C4; a linear or branched alkoxy radical, in C1-C4.

[0053] According to a preferred embodiment of the invention, the compound(s) derived from dibenzoylmethane are selected, alone or in mixtures, from among 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, the 2,5-dimethyldibenzoylmethane, 4,4'-düsopropyldibenzoylmethane, 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'-methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane, l-(4-tert-butylphenyl)-3-(2-hydroxyphenyl)propane-l,3-dione, l-(4-methoxy-l-benzofuran-5-yl)-3-phenylpropane-l,3-dione; preferably chosen, alone or in mixture, from 4-tert-butyl-4'-methoxydibenzoylmethane and / or 4-isopropyldibenzoylmethane; preferably chosen from 4-tert-butyl-4'-methoxydibenzoylmethane.

[0054] By way of example, 4-isopropyldibenzoylmethane is sold under the name "EUSOLEX 9020" by the company MERCK, and 4-tert-butyl-4'-methoxydibenzoylmethane or butyl methoxy dibenzoylmethane, with the formula: [formula 7]

[0055] is sold under the name "PARSOL 1789" by the company DSM Nutritional products.

[0056] By way of further example, the l-(4-methoxy-l-benzofuran-5-yl)-3-phenylpropane-l,3-dione, of formula: [formula 8]

[0057] According to a particularly preferred embodiment, the composition according to the invention comprises 4-tert-butyl-4'-methoxydibenzoylmethane (INCI name: butyl methoxy dibenzoylmethane).

[0058] When present, 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 preferably between 0.3 and 5% by weight, relative to the total weight of the composition. ADDITIONAL ACRYLIC POLYMER

[0059] According to a particular embodiment of the invention, the composition comprises at least one polymer comprising monomeric units of formulas (A) and (B) defined below: [Formula A] [Formula B] RI, independently of each other, is chosen from among the alkyl or alkylene radicals, and at least 60% by weight of the RI groups are radicals selected from stearyl and behenyl radicals, the weight percentage referring to the sum of all RI groups present in the polymer, and the weight ratio of the sum of all hydroxyethyl acrylate units to the sum of all acrylate units bearing the RI group ranges from 1:30 to 1:1 , and the sum of the total units A and B is at least 95% by weight of the total weight of the polymer.

[0060] Preferably, RI consists of alkyl radicals, preferably C16-C22 alkyl radicals, and more preferably stearyl radicals (in Cl8) or behenyl radicals (in C22).

[0061] Preferably, at least 70% by weight of the RI groups are stearyl or behenyl radicals, preferably at least 80% by weight, more preferably at least 90% by weight.

[0062] According to a preferred embodiment, all RI groups are behenyl radicals.

[0063] According to another preferred embodiment, all RI groups are stearyl radicals.

[0064] Preferably, said weight ratio goes from 1:15 to 1:1, preferably goes from 1:10 to 1:4.

[0065] Advantageously, the polymeric units present in the polymer consist of the units (A) and (B) described previously.

[0066] The polymer has a number-average molecular weight (Mn) ranging from 2,000 to 9,000 g / mol, preferably ranging from 5,000 to 9,000 g / mol. The number-average molecular weight can be measured using gel permeation chromatography, for example according to the method described in the example below.

[0067] Preferably, the polymer has a melting temperature ranging from 40 °C to 70 °C, and preferably from 45 °C to 67 °C. The melting temperature is measured by differential scanning calorimetry (DSC), for example according to the method described in the example below.

[0068] According to a first embodiment, when the polymer is such that at least 60% by weight of the RI groups are stearyl radicals, then the polymer preferably has a melting point ranging from 40 to 60 °C, and preferably ranging from 45 to 55 °C.

[0069] According to a second embodiment, when the polymer is such that at least 60% by weight of the RI groups are behenyl radicals, then the polymer has a melting temperature ranging from 60 °C to 70 °C, and preferably from 63 °C to 67 °C.

[0070] The polymer used according to the invention can be prepared by polymerization of monomer of formula CH2=CH-COO-R1, RI having the meaning described previously, and 2-hydroxyethyl acrylate.

[0071] Polymerization can be carried out according to known methods, such as solution polymerization or emulsion polymerization.

[0072] Polymerization is described for example in US document 2007 / 0264204.

[0073] The acrylic polymer(s) as defined above may be present in the composition according to the invention in an active material content 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 ranging from 0.2 to 3% by weight. FAT PHASE

[0074] The composition according to the invention may comprise at least one fatty phase.

[0075] For the purposes of the invention, the term "fatty phase" means a phase comprising at less a fatty substance, in particular liquid, solid or pasty, and all the liposoluble and lipophilic ingredients used for the formulation of the compositions of the invention.

[0076] According to a particular embodiment, the composition according to the invention comprises at least one oil.

[0077] Oil means any fatty substance in liquid form at room temperature (20-25°C) and atmospheric pressure (760 mm Hg).

[0078] The oily phase may include in particular at least one volatile or non-volatile hydrocarbon oil and / or a volatile and / or non-volatile silicone oil and / or a volatile and / or non-volatile fluorinated oil.

[0079] For the purposes of the present invention, "siliconized oil" means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0080] The term "hydrocarbon oil" refers to an oil containing primarily hydrogen and carbon atoms and possibly one or more heteroatoms, in particular nitrogen and oxygen. Thus, these oils may notably contain one or more carboxy, ester, ether, or hydroxy functions.

[0081] The term “fluoridated oil” means an oil comprising at least one fluorine atom.

[0082] For the purposes of this invention, "volatile oil" means an oil capable of evaporate upon contact with the skin or keratin fiber in less than one hour, at room temperature and atmospheric pressure. The volatile oil(s) of the invention are volatile cosmetic oils, liquid at room temperature, having a non-zero vapor pressure, at room temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40,000 Pa (103 to 300 mm Hg), in particular ranging from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mm Hg).

[0083] By "non-volatile oil" is meant an oil that remains on the skin or keratin fiber at room temperature and atmospheric pressure for at least several hours and, in particular, has a vapor pressure of less than 103 mm Hg (0.13 Pa). Hydrocarbon oils

[0084] The composition according to the invention may include at least one C2-C22 di- or tricarboxylic acid ester and C1-C24 alcohols.

[0085] The C2-C22 di- or tricarboxylic acids are in particular selected from citric acid, malic acid, malonic acid, succinic acid, adipic acid, maleic acid, fumaric acid, tartaric acid, isocitric acid and mixtures thereof. Preferably the acids are citric acid and adipic acid, and even more preferably citric acid.

[0086] The C1-C24 alcohols are not oxyalkylated. They may be aliphatic, cyclic, or aromatic, having from 1 to 24 carbon atoms. They are notably selected from phenol, benzyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, methanol, ethanol, propanol, n-butanol, t-butanol, pentanol, and hexanol. Preferably, the alcohol(s) are C1-C6 and can be chosen from methanol, ethanol, propanol, n-butanol, t-butanol, pentanol, hexanol, and even more preferentially ethanol.

[0087] The C2-C22 di- or tricarboxylic acid ester(s) and C1-C24 alcohol ester(s) can be mono- or poly-esterified.

[0088] By monoesterified, it is understood that only one of the two or three carboxylic acid functions is esterified. By polyesterified, it is understood that at least two carboxylic acid functions are esterified.

[0089] The di- or tricarboxylic acid can be esterified by several different alcohols. Preferably, it is esterified by a single alcohol.

[0090] According to a particular embodiment of the invention, the composition comprises at least one C3-C22 tricarboxylic acid ester and C1-C24 alcohols, preferably C1-C6. This or these esters may be mono-, di- or tri-esterified.

[0091] Monoesterified means that only one of the three carboxylic acid groups is esterified. Diesterified means that two of the three carboxylic acid groups are esterified. Triesterified means that all three carboxylic acid groups are esterified.

[0092] According to a particular embodiment of the invention, the C3-C22 tricarboxylic acid ester(s) and C1-C6 alcohol ester(s) are tri-esterified.

[0093] According to a particular embodiment of the invention, the C3-C22 tricarboxylic acid ester(s) and C1-C6 alcohol ester(s) are selected from the compounds of the following formula (9): (R1O-CO)CH2-C(R)(OC-OR2)-CH2(OC-OR3) in which: RI, R2 and R3 represent, independently of each other, a hydrogen atom or a monovalent hydrocarbon group, saturated or unsaturated, aliphatic, cyclic or aromatic, having from 1 to 6 carbon atoms; R represents a hydrogen atom or a hydroxyl radical.

[0094] According to a preferred embodiment, RI, R2, and R3 represent, independently of each other, a hydrogen atom or an alkyl radical, linear or branched, substituted or unsubstituted, preferably unsubstituted, in the C1-C6 configuration, and in particular a radical selected from among the methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, and hexyl radicals. Preferably, RI, R2, and R3 are selected independently of each other from among a hydrogen atom and the methyl, ethyl, propyl, n-butyl, and t-butyl radicals.

[0095] According to a preferred embodiment of the invention, the radicals RI, R2 and R3 are identical and are chosen from among the alkyl radicals in C1-C6, preferably in C1-C4, and even more preferably they are ethyl radicals.

[0096] According to a preferred embodiment of the invention, R represents a hydroxyl radical.

[0097] According to a particular embodiment of the invention, the ester of tricarboxylic acid and C1-C6 alcohols has the following formula: [Formula 10]

[0098] As an example of a C3-C22 tricarboxylic acid ester and C1-C6 alcohols of formula (10) and INCI name TRIETHYL CITRATE, we will cite that which is marketed under the name CITROFOL AI EXTRA by the company JUNG-BUNZLAUER.

[0099] Examples of non-volatile hydrocarbon oils that can be used according to the invention include: (i) vegetable hydrocarbon oils such as glyceride triesters, which are generally triesters of fatty acids and glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, the latter being linear or branched, saturated or unsaturated; these oils include wheat germ, sunflower, grape seed, sesame, maize, apricot, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, and rosehip oils; or even the triglycerides of caprylic / capric acids such as those sold by the company Stéa-rineries Dubois or those sold under the names Miglyol 810®, 812® and 818® by the company Dynamit Nobel; (ii) synthetic ethers having 10 to 40 carbon atoms; (iii) linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as paream, squalane, and mixtures thereof; (iv) synthetic esters such as oils of formula RCOOR' in which R represents the remainder of a linear or branched fatty acid comprising from 1 to 40 carbon atoms and R' represents a hydrocarbon chain, particularly a branched one, containing from 1 to 40 carbon atoms, provided that R + R' is > 10, such as, for example, Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12-C15 alcohol benzoate, such as the product sold under the denomination commercial name “Finsolv TN®” or “Witconol TN®” by the company WITCO or “TEGOSOFT TN ®” by the company EVONIK GOLDSCHMIDT, 2-ethylphenyl Benzoate as the commercial product sold under the name “X-TEND 226®” by the company ISP, isopropyl lanolate, hexyl laurate, dii-sopropyl adipate, isononyl isononanoate, oleyl erucate, 2-ethylhexyl palmitate, isostearyl isostearate, diisopropyl sebacate as the product sold under the name “Dub Dis” by the company Stearinerie Dubois, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, di-isostearyl malate; and pentaerythritol esters;citrates or tartrates such as linear C12-C13 dialkyl tartrates like those sold under the name COSMACOL ETI® by ENICHEM AUGUSTA INDUSTRIALE and linear C14-C15 dialkyl tartrates like those sold under the name COSMACOL ETL® by the same company; acetates; (v) fatty alcohols that are liquid at room temperature with a branched and / or unsaturated carbon chain having 12 to 26 carbon atoms such as octyl dodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol; (vi) higher C12-C22 fatty acids, such as oleic acid, linoleic acid, linolenic acid; (vii) carbonates such as dicaprylyl carbonate such as the product sold under the name “Cetiol CC®” by the company Cognis; and their mixtures.

[0100] Among the non-volatile hydrocarbon oils usable according to the invention, glyceride triesters, and in particular caprylic / capric acid triglycerides, synthetic esters, and in particular diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, dicaprylyl carbonate, isononyl isononanoate, oleyl erucate, C12-C15 alcohol benzoate, 2-ethylphenyl benzoate, and fatty alcohols, in particular octyldodecanol, are preferred. Preferably, the non-volatile hydrocarbon oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate, and dicaprylyl carbonate.

[0101] Examples of usable volatile hydrocarbon oils according to the invention include hydrocarbon oils having 8 to 16 carbon atoms, and in particular C8-Ci6 branched alkanes such as petroleum-derived C8-Ci6 isoalkanes (also called isoparaffins) such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, oils sold under the trade names Isopars or Permetyls, C8-Ci6 branched esters, isohexyl neo-pentanoate, and mixtures thereof.

[0102] Also citeable are the alkanes described in Cognis patent applications WO 2007 / 068371 and WO 2008 / 155059 (mixtures of distinct alkanes differing by at least one carbon atom). These alkanes are obtained from fatty alcohols, themselves obtained from coconut or palm oil. Examples include the mixtures of n-undecane (Cn) and n-tridecane (Ci3) obtained in Examples 1 and 2 of Cognis application WO 2008 / 155059. Also citeable are n-dodecane (Ci2) and n-tetradecane (Ci4) sold by Sasol under the references PARAFOL 12-97 and PARAFOL 14-97®, respectively, as well as mixtures thereof.

[0103] Other volatile hydrocarbon oils such as petroleum distillates, particularly those sold under the name Shell Soit® by the Shell company, may also be used. In one embodiment, the volatile solvent is selected from volatile hydrocarbon oils having 8 to 16 carbon atoms and mixtures thereof. Silicone oils

[0104] Non-volatile silicone oils can be selected in particular from non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes having alkyl or alkoxy groups, during and / or at the end of the silicone chain, each group having from 2 to 24 carbon atoms, phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl trimethylsiloxy silicas.

[0105] Examples of volatile silicone oils include volatile linear or cyclic silicone oils, particularly those having a viscosity < 8 centistokes (8 x 10⁶ m² / s), and having in particular 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having 1 to 10 carbon atoms. Examples of volatile silicone oils usable in the invention include octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyl octyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.

[0106] A fatty phase according to the invention may further comprise, mixed with or solubilized in the oil, other fatty substances.

[0107] Another fatty substance that may be present in the fatty phase may be, for example: - a fatty acid chosen from fatty acids having 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, Camauba or Candellila wax, rice bran wax, paraffin waxes, lignite or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; - a gum chosen from among the silicone gums (dimethiconol), - a paste compound, such as polymeric or non-polymer silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives, - and mixtures thereof.

[0108] Preferably, the overall fatty phase, including all lipophilic substances other than lipophilic filters of the composition that can be solubilized in this same phase, represents from 5 to 95% by weight, and preferably from 10 to 80% by weight relative to the total weight of the composition. AQUEOUS PHASE

[0109] The composition according to the invention may comprise at least one aqueous phase.

[0110] The aqueous phase contains water, and possibly other organic solvents soluble or miscible in water.

[0111] An aqueous phase suitable for the invention may include, for example, water chosen from a natural spring water, such as La Roche-Posay water, Vittel water, Saint Gervais Mont Blanc water, or Vichy waters, or a floral water.

[0112] According to a particular embodiment of the invention, the overall aqueous phase, including all hydrophilic substances of the composition capable of being solubilized in this same phase, represents from 1 to 99% by weight, and preferably from 10 to 80% by weight relative to the total weight of the composition. ADDITIVES

[0113] Additional UV filters

[0114] The compositions according to the invention may additionally contain one or more complementary UV filters selected from hydrophilic, lipophilic, or insoluble organic UV filters and / or one or more mineral pigments. Preferably, it will consist of at least one hydrophilic, lipophilic, or insoluble organic UV filter.

[0115] By "hydrophilic UV filter" is meant any organic or inorganic cosmetic or dermatological compound that filters UV radiation and is capable of being completely dissolved in molecular form in a liquid aqueous phase or of being solubilized in colloidal form (for example in micellar form) in a liquid aqueous phase.

[0116] By "lipophilic filter" is meant any organic or inorganic cosmetic or dermatological compound that filters UV radiation and is capable of being completely dissolved in molecular form in a liquid oil phase or of being solubilized in colloidal form (for example in micellar form) in a liquid oil phase.

[0117] By "insoluble UV filter" is meant any organic or inorganic compound A cosmetic or dermatological UV-filtering product with a water solubility of less than 0.5% by weight and a solubility of less than 0.5% by weight in most organic solvents, such as paraffin oil, fatty alcohol benzoates, and fatty acid triglycerides, for example, Miglyol 812® marketed by Dynamit Nobel. This solubility, measured at 70°C, is defined as the amount of product dissolved in the solvent at equilibrium, with an excess of suspended solids after returning to room temperature. It can easily be evaluated in the laboratory.

[0118] Complementary organic UV filters are selected in particular from cinnamic compounds; anthranilate compounds; salicylic compounds; benzylidene camphor compounds; benzophenone compounds; [3,[3-diphenyl acrylate] compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in US patent 5624663; benzimidazole derivatives; imidazoline compounds; bis-benzoazolyl compounds as described in patents EP669323 and US 2,463,264; p-aminobenzoic compounds (PABA); methylene bis-(hydroxyphenyl benzotriazole) compounds as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; benzoxazole compounds as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; filter polymers and filter silicones such as those described in particular in application WO-93 / 04665;α-Alkylstyrene-derived dimers such as those described in patent application DE19855649; 4,4-Diarylbutadiene compounds such as those described in applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EPI 133980 and EPI33981 and mixtures thereof.

[0119] Examples of organic photoprotective agents include those designated below by their INCI name.

[0120] Cinnamic compounds: Ethylhexyl Methoxycinnamate, sold notably under the trade name PARSOL MCX ® by DSM Nutritial Products Isopropyl Methoxycinnamate Isoamyl p-Methoxycinnamate sold under the trade name NEO HELIOPAN E 1000 ® by Symrise DEA Methoxycinnamate, Diisopropyl Methylcinnamate, Glyceryl Ethylhexanoate Dimethoxycinnamate.

[0121] Para-aminobenzoic compounds: PABA, Ethyl PABA, Ethyl Dihydroxypropyl PABA, Ethylhexyl Dimethyl PABA, sold notably under the name "ESCALOL 507®" by ISP, Glyceryl PABA, PEG-25 PABA sold under the name "UVINUL P 25®" by BASF.

[0122] Salicvillic compounds: Homosalate sold under the name "Eusolex HMS®" by Rona / EM Industries, Ethylhexyl Salicylate sold under the name "NEO HELIOPAN OS®" by Symrise, Dipropyleneglycol Salicylate sold under the name "DIPSAL ®" by SCHER, TEA Salicylate, sold under the name "NEO HELIOPAN TS®" by Symrise.

[0123] Compounds [3.[3-diphenylacrylate: Octocrylene, sold notably under the trade name "UVINUL N 539®" by BASF, Etocrylene, sold notably under the trade name "UVINUL N 35®" by BASF.

[0124] Benzophenone compounds: 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 "UVINUL M 40®" by BASF, Benzophenone-4 sold under the trade name "UVINUL MS 40®" by BASF, Benzophenone-5, 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 in mixture with octylmethoxycinnamate under the trade name "UVINUL A Plus B®" by BASF, 1,1'-(1,4-piperazinediyl)bis[l-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-metha none (CAS 919803-06-8) as described in application WO2007 / 071584; this compound being advantageously used in micronized form (average size of 0.02 to 2 pm) which can be obtained for example by the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in aqueous dispersion form.

[0125] Benzylidene camphor compounds: 3-Benzylidene camphor manufactured under the name "MEXORYL SD®" by CHIMEX, 4-Methylbenzylidene camphor sold under the name "EUSOLEX 6300®" by MERCK, Benzylidene Camphor Sulfonic Acid manufactured under the name "MEXORYL SL®" by CHIMEX, Camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL SO®" by CHIMEX, Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name "MEXORYL SX®" by CHIMEX, Polyacrylamidomethyl Benzylidene Camphor manufactured under the name "MEXORYL SW®" by CHIMEX.

[0126] Phenyl benzimidazole compounds: Phenylbenzimidazole Sulfonic Acid sold notably under the trade name "EUSOLEX 232®" by MERCK.

[0127] Bis-benzoazolyl compounds: Disodium Phenyl Dibenzimidazole Tetra-sulfonate sold under the trade name "NEO HELIOPAN AP®" by Haarmann and REIMER.

[0128] Phenyl benzotriazole compounds: Drometrizole Trisiloxane sold under the name "Silatrizole®" by RHODIA CHIMIE.

[0129] Compounds methylene bis-hydroxyphenyl benzotriazole): Methylene bis-Benzotriazolyl Tetramethylbutylphenol, notably in solid form such as the product sold under the trade name "MIXXIM BB / 100 ®" by FAIRMOUNT CHEMICAL, or as an aqueous dispersion of micronized particles having an average particle size ranging from 0.01 to 5 µm and more preferably from 0.01 to 2 µm and more particularly from 0.020 to 2 µm, with at least one alkyl polyglycoside surfactant of the structure CnH2n+1 O(C6HiO5)xH, where n is an integer from 8 to 16 and x is the average degree of polymerization of the unit (C6HiO5) and ranges from 1.4 to 1.6, as described in patent GB-A-2 303 549, notably sold under the trade name "TINOSORB M®" by BASF, or as an aqueous dispersion of micronized particles having an average particle size ranging from 0.02 to 2pm and more preferably from 0.01 to 1.5pm and more particularly from 0,02 to 1 pm in the presence of at least one mono-(C8-C2o)alkyl-ester of polyglycerol having a degree of glycerol polymerization of at least 5 such as the aqueous dispersions described in application WO2009 / 063392.

[0130] Triazine compounds: - 3,3'-(l,4-Phenylene)bis(5,6-diphenyl-l,2,4-triazine), INCI name Phenylene Bis-Diphenyl triazine, with the following chemical formula: [Formula 11] - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the trade name "TINOSORB S®" by BASF, - Ethylhexyl Triazone, sold notably under the trade name "UVINUL T 150®" by BASF, - Diethylhexyl Butamido Triazone sold under the trade name "UVASORB HEB ®" by SIGMA 3V, - 2,4,6-tris-(4'-aminobenzalmalonate of dineopentyl)-s-triazine, - 2,4,6-tris-(4'-aminobenzalmalonate of diisobutyl)-s-triazine, - 2,4-bis-(4'-aminobenzoate of n-butyl)-6-(aminopropyltrisiloxane)-s-triazine, - 2,4-bis-(4'-aminobenzalmalonate of dineopentyl)-6-(4'-aminobenzoate of n-butyl)-s-triazine, - Symmetrical triazine filters substituted with naphthalenyl or polyphenyl groups described in US patent 6,225,467, application WO2004 / 085412 (see compounds 6 and 9) or the document "Symetrical Triazine Derivatives" IP.COM IPCOM000031257 Journal, INC WEST HENRIETTA, NY, US (September 20, 2004), in particular 2,4,6-tris(di-phenyl)-triazine and 2,4,6-tris(ter-phenyl)-triazine, which is included in patent applications WO06 / 035000, WO06 / 034982, WO06 / 034991, WO06 / 035007, WO2006 / 034992, WO2006 / 034985, these compounds being advantageously used in micronized form (average size of particles from 0.02 to 3 pm) which can be obtained for example by the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in aqueous dispersion form, - triazine silicones substituted by two aminobenzoate groups as described in patent EP0841341 in particular 2,4-bis-(n-butyl 4'-aminobenzalmalonate)-6-[(3-{l,3,3,3-tetramethyl-l-[(trimethylsilyloxy]disiloxanyl}propyl)amino]-s-triazine.

[0131] Anthranilic compounds: Menthyl anthranilate sold under the trade name "NEO HELIOPAN MA®" by Symrise.

[0132] Imidazoline compounds: Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate.

[0133] Benzalmalonate compounds: Polyorganosiloxane with benzalmalonate functions such as Polysilicone-15 sold under the trade name "PARSOL SLX ®" by HOFFMANN LA ROCHE.

[0134] 4,4-diarvlbutadiene compounds: -1,1-dicarboxy (2,2'-dimethyl-propyl)-4,4-diphenylbutadiene.

[0135] Benzoxazole compounds: 2,4-bis-[5-l(dimethylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imi no-l,3,5-triazine sold under the name Uvasorb K2A® by Sigma 3V.

[0136] The preferred organic filters are chosen from: Ethylhexyl Methoxycinnamate Ethylhexyl Salicylate, Homosalate, Octocrylene Phenylbenzimidazole Sulfonic Acid, Benzophenone-3 Benzophenone-4 Benzophenone-5, 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyle, 4-Methylbenzylidene camphor, Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetra-sulfonate, Méthylène bis-Benzotriazolyl Tetramethylbutylphénol, Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine Ethylhexyl Triazone, Diethylhexyl Butamido Triazone, 2,4,6-tris-(4’-amino benzalmalonate de dinéopentyle)-s-triazine, 2,4,6-tris-(4’-amino benzalmalonate de diisobutyle)-s- triazine, 2,4-bis-(4’-aminobenzoate de n-butyle)-6-(aminopropyltrisiloxane)-s-triazine, 2,4-bis-(4’-aminobenzalmalonate de dinéopentyle)-6-(4’-aminobenzoate de n-butyle)-s-triazine, 2,4-bis-(n-butyl 4’-aminobenzalmalonate)-6-[(3-{ l,3,3,3-tetramethyl-l-[(trimethylsilyloxy]disiloxanyl}propyl)amino]-s-triazine, 2,4,6-tris-(di-phenyl)-triazine, 2,4,6-tris-(ter-phenyl)-triazine Drometrizole Trisiloxane, Polysilicone-15, 1,1-dicarboxy (2,2'-dimethyl-propyl)-4,4-diphenylbutadiene, 2,4-bis-[5-l(dimethylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imin ol,3,5-triazine, and mixtures thereof.

[0137] The particularly preferred organic filters are chosen from: Ethylhexyl Salicylate, Homosalate, Octocrylene, n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate, Terephthalylidene Dicamphor Sulfonic Acid, Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, Ethylhexyl Triazone, Diethylhexyl Butamido Triazone, 2,4-bis-(n-butyl 4'-aminobenzalmalonate)-6-[(3-{ l,3,3,3-tetramethyl-l-[(trimethylsilyloxy]disiloxanyl}propyl)amino]-s-triazine, Drometrizole Trisiloxane, and mixtures thereof.

[0138] The inorganic UV filters used according to the present invention are metal oxide pigments. More preferably, the inorganic UV filters of the invention are metal oxide particles having an average elementary particle size less than or equal to 0.5 pm, more preferably between 0.005 and 0.5 pm and even more preferably between 0.01 and 0.2 pm, even better between 0.01 and 0.1 pm, and more particularly between 0.015 and 0.05 pm.

[0139] They may in particular be chosen from titanium, zinc, iron, zirconium, cerium oxides or mixtures thereof.

[0140] Such metallic oxide pigments, coated or uncoated, are described in particular in patent application EP-A-0 518 773. As commercial pigments, we can mention the products sold by the companies SACHTLEBEN PIGMENTS, TAYCA, MERCK and DEGUSSA.

[0141] Metal oxide pigments may be coated or uncoated.

[0142] Coated pigments are pigments that have undergone one or more surface treatments of a 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 aluminum salts of fatty acids, metal alkoxides (titanium or aluminum), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides, or sodium hexametaphosphate.

[0143] The coated pigments are more particularly coated titanium oxides: - silica products such as "SUNVEIL®" from the company IKEDA, - silica and iron oxide such as the product "SUNVEIL F®" from the company IKEDA, - of silica and alumina such as the products "MICROTITANIUM DIOXIDE MT 500 SA®" and "MICROTITANIUM DIOXIDE MT 100 SA" from the company TAYCA, "TIOVEIL" from the company TIOXIDE, - 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, - of alumina and aluminum stearate such as the products "MICROTITANIUM DIOXIDE MT 100 T®, MT 100 TX®, MT 100 Z®, MT-01®" from the company TAYCA, the products "Solaveil CT-10 W®" and "Solaveil CT 100®" from the company UNIQEMA and the product "Eusolex T-AVO®" from the company MERCK, - of silica, alumina and alginic acid such as the product "MT-100 AQ®" from the company TAYCA, - of alumina and aluminum laurate such as the product "MICROTITANIUM DIOXIDE MT 100 S®" from the company TAYCA, - iron oxide and iron stearate such as the product "MICROTITANIUM DIOXIDE MT 100 F®" from the company TAYCA, - zinc oxide and zinc stearate such as the product "BR 351®" from the company TAYCA, - of silica and alumina and treated with silicone such as the products "MICRO-TITANIUM DIOXIDE MT 600 SAS®", "MICROTITANIUM DIOXIDE MT 500 SAS®" or "MICROTITANIUM DIOXIDE MT 100 SAS®" from the company TAYCA, - of silica, alumina, aluminum stearate and treated with silicone such as the product "STT-30-DS®" from the company TITAN KOGYO, - of silica and treated with a silicone such as the product "UV-TITAN X 195®" from the company SACHTLEBEN PIGMENTS, - of alumina and treated with silicone such as the products "TIPAQUE TTO-55 (S)®" from the company ISHIHARA, or "UV TITAN M 262®" from the company SACHTLEBEN PIGMENTS, - triethanolamine such as the product "STT-65-S" from the company TITAN KOGYO, - stearic acid such as the product "TIPAQUE TTO-55 (C)®" from the company ISHIHARA, - of sodium hexametaphosphate such as the product "MICRO-TITANIUM DIOXIDE MT 150 W®" from the company TAYCA. - TiO2 treated with octyl trimethyl silane sold under the trade name "T 805®" by the company DEGUSSA SILICES, - TiO2 treated with a polydimethylsiloxane sold under the trade name "70250 Cardre UF TiO2SI3®" by the company CARDRE, - TiO2 anatase / rutile treated with a polydimethylhydrogenosiloxane sold under the trade name "MICRO TITANIUM DIOXIDE USP GRADE HY-DROPHOBIC®" by the company COLOR TECHNIQUES, - TiO2 coated with triethylhexanoin, aluminum stearate, alumina sold under the trade name Solaveil CT-200-LQ-(WD) by CRODA, - TiO2 coated with aluminium stearate, alumina and silicone sold under the trade name Solaveil CT-12W-LQ-(WD from CRODA), - TiO2 coated with lauroyl lysine sold by Daito Kasei Kogyo under the name LL 5 Titanium Dioxide CR 50, - TiO2 coated with C9-15 fluoroalcohol phosphate and aluminium hydroxide sold by Daito Kasei Kogyo under the name PFX-5 TiO2 CR-50.

[0144] Other examples include TiO2 pigments doped with at least one transition metal such as iron, zinc, manganese, and more particularly manganese. Preferably, these doped pigments are in the form of an oily dispersion. The oil present in the oily dispersion is preferably selected from triglycerides, including those of capric / caprylic acids. The oily dispersion of titanium dioxide particles may also include one or more dispersing agents, such as a sorbitan ester like sorbitan isostearate, a polyoxyalkylated fatty acid and glycerol ester like TRLPPG3 MYRISTYLETHER CITRATE and POLYGLYCERYL-3 POLYRICINOLEATE. Preferably, the oily dispersion of titanium dioxide particles includes at least one dispersing agent selected from polyoxyalkylated fatty acid and glycerol esters.One can cite in particular the oily dispersion of manganese-doped TiO2 particles in capric / caprylic acid triglyceride in the presence of TRLPPG-3 MYRISTYLETHER CITRATE and POLYGLYCERYL-3-POLYRICINOLEATE and SORBITAN ISOSTEARATE, INCI name: TITANIUM DIOXIDE (and) TRLPPG-3 MYRISTYLETHER CITRATE (and) POLYGLYCERYL-3 RICINOLEATE (and) SORBITAN ISOSTEARATE, as the product sold under the trade name OPTISOL TD50 ® by the company CRODA. .

[0145] Uncoated titanium oxide pigments are, for example, sold by TAYCA under the trade names "MICROTITANIUM DIOXIDE MT 500 B" or "MICROTITANIUM DIOXIDE MT600 B®", by DEGUSSA under the name "P 25", by WACKHER under the name "Transparent Titanium Oxide PW®", by MIYOSHI KASEI under the The name "UFTR®", by the company TOMEN under the name "ITS®" and by the company TIOXIDE under the name "TIOVEIL AQ".

[0146] Uncoated zinc oxide pigments include, for example: - those marketed under the name "Z-cote" by the company Sunsmart; - those marketed under the name "Nanox®" by the company Elementis; - those marketed under the name "Nanogard WCD 2025®" by the company Nanophase Technologies.

[0147] Coated zinc oxide pigments are, for example: - those marketed under the name "Zinc Oxide CS-5®" by the company Toshibi (ZnO coated with polymethylhydrogenesiloxane); - those marketed under the name "Nanogard Zinc Oxide FN®" by the company Nanophase Technologies (in 40% dispersion in Finsolv TN®, C12-C15 alcohol benzoate); - those marketed under the name "DAITOPERSION Zn-30®" and "DAL TOPERSION Zn-50®" by the company Daito (dispersions in cyclopolymethylsiloxane / oxyethylenated polydimethylsiloxane, containing 30% or 50% of zinc oxides coated by silica and polymethylhydrosiloxane); - those marketed under the name "NFD Ultrafine ZnO®" by the company Daikin (ZnO coated with perfluoroalkyl phosphate and perfluoroalkylethyl copolymer dispersed in cyclopentasiloxane); - those marketed under the name "SPD-Z1®" by the company Shin-Etsu (ZnO coated by silicone-grafted acrylic polymer, dispersed in cyclodimethyl-siloxane); - those marketed under the name "Escalol Z100®" by the company ISP (ZnO treated with alumina and dispersed in the mixture of ethylhexyl methoxycinnamate / PVP-hexadecene copolymer / methicone); - those marketed under the name "Fuji ZnO-SMS-10®" by the company Fuji Pigment (ZnO coated with silica and polymethylsilsesquioxane); - those marketed under the name "Nanox Gel TN®" by the company Elementis (ZnO dispersed at 55% in C12-C15 alcohol benzoate with hydroxystearic acid polycondensate).

[0148] Uncoated cerium oxide pigments may be, for example, those sold under the name "COLLOIDAL CERIUM OXIDE®" by the company RHONE POULENC.

[0149] Uncoated iron oxide pigments are, for example, sold by the company ARNAUD under the names "NANOGARD WCD 2002® (FE 45B®)", "NANOGARD IRON FE 45 BL AQ", "NANOGARD FE 45R AQ®", "NANOGARD WCD 2006 ® (FE 45R®)", or by the company MITSUBISHI under the name "TY- 220®".

[0150] Coated iron oxide pigments are for example sold by the company ARNAUD under the names "NANOGARD WCD 2008 (FE 45B FN)®", "NANOGARD WCD 2009® (FE 45B 556®)", "NANOGARD FE 45 BL 345®", "NANOGARD FE 45 BL®", or by the company BASF under the name "OXIDE DE FER TRANSPARENT®".

[0151] We can also mention mixtures of metal oxides, in particular of titanium dioxide and 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®", as well as 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 glycerin such as the product "M 211®" sold by the company SACHTLEBEN PIGMENTS.

[0152] According to the invention, titanium oxide pigments, coated or uncoated, are particularly preferred.

[0153] The additional UV filters 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 relative to the total weight of the composition. Other additives

[0154] The composition according to the present invention may further comprise conventional cosmetic adjuvants in particular selected from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoaming agents, perfumes, preservatives, anionic, cationic, non-ionic, zwit-terionic or amphoteric surfactants, actives, fillers, polymers, propellants, alkalizing or acidifying agents or any other ingredient commonly used in the cosmetic and / or dermatological field.

[0155] Among the organic solvents, we can mention short-chain monoalcohols for example in C1-C4 such as ethanol and isopropanol, short-chain polyols in C2-C8, such as glycerin, diols such as caprylyl glycol, pentanediol-1,2, pro-panediol, 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.

[0156] According to a preferred embodiment, ethanol, propylene glycol, glycerin, and mixtures thereof may be used in particular.

[0157] Examples of thickeners include carboxyvinyl polymers such as Carbopols® (Carbomers) and Pemulen polymers such as Pemulen TRI® and Pemulen TR2® (Acrylate / C10-C30-alkylacrylate copolymer); polyacrylamides such as crosslinked copolymers sold under the names Sepigel 305® (CTFA name: polyacrylamide / Ci3-i4 isoparaffin / Laureth 7) or Simulgel 600 (CTFA name: acrylamide / sodium acryloyldimethyltaurate copolymer / isohexadecane / polysorbate 80) by the company Seppic; 2-acrylamido 2-methylpropane sulfonic acid polymers and copolymers, possibly crosslinked and / or neutralized, such as poly(2-acrylamido 2-methylpropane sulfonic acid) marketed by Hoechst under the trade name "Hostacerin AMPS®" (CTFA name: ammonium polyacryloyldimethyl taurate) or SIMULGEL 800® marketed by SEPPIC (CTFA name: sodium polyacryolyldimethyl taurate / polysorbate 80 / sorbitan oleate); 2-acrylamido 2-methylpropane sulfonic acid and hydroxyethyl acrylate copolymers such as SIMULGEL NS® and SEPINOV EMT 10® marketed by SEPPIC;Cellulosic derivatives such as hydroxyethylcellulose; polysaccharides, particularly gums such as xanthan gum; water-soluble or water-dispersible silicone derivatives such as acrylic silicones, polyether silicones, and cationic silicones and mixtures thereof.

[0158] Examples of acidifying agents include mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, and sulfonic acids.

[0159] Examples of alkalizing agents include ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides.

[0160] Preferably, the cosmetic composition comprises one or more alkalizing agents selected from alkanolamines, in particular triethanolamine, and sodium hydroxide.

[0161] Among the active ingredients for the care of keratinous materials such as skin, lips, scalp, hair, eyelashes or nails, examples include vitamins and their derivatives or precursors, alone or in mixtures; antioxidants; free radical scavengers; anti-pollution agents; self-tanning agents; anti-glycation agents; soothing agents; deodorizing agents; essential oils; NO-synthase inhibitors; agents that stimulate the synthesis of dermal or epidermal macromolecules and / or prevent their degradation; agents that stimulate fibroblast proliferation; agents that stimulate keratinocyte proliferation; muscle relaxants; cooling agents; firming agents; mattifying agents; depigmenting agents; pro-pigmenting agents; keratolytic agents; desquamating agents; moisturizing agents; anti-inflammatory agents inflammatory agents; antimicrobial agents; slimming agents; agents acting on the energy metabolism of cells; insect repellents; antagonists of substances P or CRGP; anti-hair loss agents; anti-wrinkle agents; anti-aging agents.

[0162] A person skilled in the art will choose the said active ingredient(s) according to the desired effect on the skin, hair, eyelashes, eyebrows, nails.

[0163] Of course, a person skilled in the art will take care to choose the possible complementary compound(s) mentioned above and / or their quantities in such a way that the advantageous properties intrinsically attached to the compositions according to the invention are not, or not substantially, altered by the envisaged addition(s). Pharmaceutical Forms

[0164] The compositions according to the invention may be aqueous or anhydrous.

[0165] When the compositions are aqueous, they contain at least one aqueous phase.

[0166] They can then be in purely aqueous form, that is to say, they comprise an amount of fat phase less than 10% by weight, preferably less than 5% by weight, and even more preferably less than 2% by weight relative to the total weight of the composition. Advantageously, the composition according to the invention is essentially aqueous, that is to say, it is free of fat phase.

[0167] The compositions according to the invention can also be in the form of an emulsion, simple or complex (O / W, W / W, W / W / W or W / O / W), such as a cream, a milk or a cream gel.

[0168] In the case where the composition according to the invention is aqueous, and it is possible to measure its pH, this is generally between 3 and 12 approximately, preferably between 5 and 9 approximately, and even more particularly from 5.5 to 8.

[0169] Compositions may also be in anhydrous form, such as an oil, a glycol solution, or an alcoholic solution. An "anhydrous composition" is defined as a composition containing less than 1% water by weight, or even less than 0.5% water, and in particular, free from 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 be presented as a foam or spray.

[0170] In the case of compositions in the form of oil-in-water or water-in-oil emulsions, the emulsification processes that can be used are of the blade or propeller type, rotor-stator and HHP.

[0171] To obtain stable emulsions with a low polymer content (oil / polymer ratio >25), it is possible to perform the dispersion in concentrated phase and then dilute dispersion with the rest of the aqueous phase.

[0172] It is also possible, by HHP (between 50 and 800 bars), to obtain stable dispersions with droplet sizes down to 100 nm.

[0173] Emulsions generally contain at least one emulsifier selected from amphoteric, anionic, cationic, or nonionic emulsifiers, used alone or in mixtures. The emulsifiers are chosen appropriately depending on the emulsion to be obtained (W / O or W / O).

[0174] Examples of W / O emulsifying surfactants include alkyl esters or ethers of sorbitan, glycerol, polyol, glycerol or sugars; silicone surfactants such as dimethicone copolyols like the mixture of cyclomethicone and dimethicone copolyol sold under the name "DC 5225 C®" by Dow Corning, and alkyl-dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid" by Dow Corning; Cetyl dimethicone copolyol, such as the product sold under the name Abil EM 90R® by Goldschmidt, and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles), and hexyl laurate sold under the name ABIL WE 09® by Goldschmidt, may be used. One or more co-emulsifiers may also be added, advantageously selected from the group comprising alkyl polyol esters.

[0175] We can also mention non-siliconized emulsifying surfactants, in particular alkyl esters or ethers of sorbitan, glycerol, polyol or sugars.

[0176] Examples of alkylated polyol esters include polyethylene glycol esters such as PEG-30 Dipolyhydroxystearate, such as the product marketed under the name Arlacel P135® by the company ICI.

[0177] Examples of glycerol and / or sorbitan esters include polyglycerol isostearate, such as the product marketed under the name Isolan GI 34® by Goldschmidt; sorbitan isostearate, such as the product marketed under the name Arlacel 987® by ICI; sorbitan isostearate and glycerol, such as the product marketed under the name Arlacel 986® by ICI, and mixtures thereof.

[0178] For O / W emulsions, examples of non-ionic emulsifying surfactants include polyoxyalkylated (particularly polyoxyethylated and / or polyoxypropylated) fatty acid and glycerol esters; oxyalkylated fatty acid and sorbitan esters; polyoxyalkylated fatty acid esters (particularly polyoxyethylated and / or polyoxypropylated), possibly in combination with a fatty acid and glycerol ester such as the PEG-100 Stearate / Glyceryl Stearate mixture marketed, for example, by ICI under the name Arlacel 165; oxyalkylated (oxyethylated and / or oxypropylened) fatty alcohol ethers; and esters of sugars such as sucrose stearate; fatty alcohol and sugar ethers, in particular alkyl polyglucosides (APGs) such as decyl glucoside and lauryl glucoside marketed for example by Henkel under the respective names Plantaren 2000® and Plantaren 1200®, cetostearyl glucoside possibly in mixture with cetostearyl alcohol, marketed for example under the name Montanov 68® by Seppic, under the name Tegocare CG90® by Goldschmidt and under the name Emulgade KE3302® by Henkel, as well as arachidyl glucoside, for example in the form of the mixture of arachidic and behenic alcohols and arachidyl glucoside marketed under the name Montanov 202® by Seppic.According to a particular embodiment of the invention, the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol can be in the form of a self-emulsifying composition, as described for example in document WO-A-92 / 06778.

[0179] When it is an emulsion, the aqueous phase thereof may include 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).

[0180] The compositions according to the invention find their application in a large number of treatments, in particular cosmetic, of the skin, lips and hair, including the scalp, in particular for the protection and / or care of the skin, lips and / or hair, and / or for the makeup of the skin and / or lips.

[0181] Another object of the present invention is the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and / or scalp, in particular skincare products, sun protection products and makeup products.

[0182] The cosmetic compositions according to the invention can, for example, be used as a makeup product.

[0183] Another object of the present invention is a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material consisting of applying to the surface of said keratinous material at least one composition according to the invention as defined above.

[0184] Another object of the invention is the use of di-t-butyl pentaerythrityl tetrahydroxycinnamate to photostabilize a merocyanin of formula (3) as defined above.

[0185] Another object of the invention is the use of di-t-butyl pentaerythrityl tetrahydroxycinnamate to photostabilize a merocyanin of formula (3) as defined above in the presence of one or more dibenzoylmethane derivatives, preferably in the presence of 4-(ter.-butyl) 4'-methoxy dibenzoylmethane.

[0186] The cosmetic compositions according to the invention can, for example, be used as skincare and / or sun protection products for the face and / or body, with a liquid to semi-liquid consistency, such as lotions, creams of varying textures, gel-creams, and pastes. They may optionally be packaged in aerosol form and be presented as a foam or spray.

[0187] The compositions according to the invention, in the form of vaporizable fluid lotions conforming to the invention, are applied to the skin or hair as fine particles by means of pressurization devices. The devices according to the invention are well known to those skilled in the art and include non-aerosol pumps or "atomizers," aerosol containers comprising a propellant, and aerosol pumps using compressed air as a propellant. The latter are described in US patents 4,077,441 and 4,850,517.

[0188] Aerosol compositions according to the invention generally contain conventional propellants such as, for example, hydrofluoro compounds dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane, and trichlorofluoromethane. These are preferably present in quantities ranging from 15 to 50% by weight relative to the total weight of the composition.

[0189] According to another aspect, the invention also relates to a cosmetic set comprising: (i) a container delimiting one or more compartments, said container being closed by a closing element and possibly not watertight; and ii) a makeup and / or skincare composition according to the invention arranged inside said compartment(s).

[0190] The container may, for example, be in the form of a pot or a case.

[0191] The closure element may be in the form of a lid comprising a hood mounted movable by translation or pivoting relative to the container housing the said makeup and / or skincare composition(s). EXAMPLES

[0192] The following examples serve to illustrate the invention without, however, being intended to be limiting.

[0193] Example A1: Preparation of compound (14) [Formula 14]

[0194] 122.23 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 grams of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally a solvent.

[0195] The base / solvent combinations indicated in the following table are used. [Tables 2] Example Base Solvent Example ALI DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A 1.2 Triethylamine isopropanol Example A 1.3 3-Methoxypropylamine isopropanol Example A 1.4 3-Methoxypropylamine tert-amyl alcohol Example A 1.5 3-Methoxypropylamine toluene Example A 1.6 3-Methoxypropylamine dimethylformamide Example A 1.7 Solvent-free 3-Methoxypropylamine Example A 1.8 N-Morpholine isopropanol

[0196] The completion of the alkylation reaction can be monitored, for example, by methods such as TLC, GC or HPLC.

[0197] 162.30 grams of compound (14) are obtained in the form of a brown oil.

[0198] After crystallization, the product is obtained in the form of yellowish crystals.

[0199] Melting point: 92.7 °C.

[0200] Example A2: Preparation of compound (15) [Formula 15]

[0201] 101.00 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 grams of 2-cyano-N-(3-methoxy-propyl)-acetamide in approximately equimolar proportions in the presence of a base and optionally a solvent.

[0202] The base / solvent combinations indicated in the following table are used. [Tables 3] Example Solvent Base 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 Example A2.6 3-Methoxypropylamine dimethylformamide Example A2.7 3-Methoxypropylamine solvent-free

[0203] The crude product (15) is obtained in the form of a dark brown oil.

[0204] After silica gel column chromatography (eluent: toluene / methanol) 99 / 1), 81.8 grams of product are obtained in the form of yellowish crystals.

[0205] Melting point: 84.7-85.3 °C.

[0206] Example A3: Preparation of compound (27) [formula 27]

[0207] 13.09 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 10.12 grams of isobutyl cyanoacetate in the presence of a base and optionally a solvent.

[0208] The base / solvent combinations indicated in the following table are used. [Tables 4] Example Solvent Base 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 A3.7 Solvent-free 3-Methoxypropylamine

[0209] 15.97 grams of crude product (27) are obtained in the form of a dark brown oil.

[0210] After silica gel column chromatography (eluent: toluene / acetone), 13.46 grams of product are obtained in the form of yellowish crystals.

[0211] Melting point: 96.3 °C.

[0212] Example A4: Preparation of compound (25) [formula 25]

[0213] 148.4 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-l-one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 grams of 2-ethoxyethyl cyanoacetate in the presence of an organic base and a solvent.

[0214] The base / solvent combinations indicated in the table below are used. [Tables 5] Example Solvent Base 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 Example A4.6 3-Methoxypropylamine dimethylformamide Example A4.7 Solvent-free 3-Methoxypropylamine

[0215] Example of preparation of acrylic polymers:

[0216] Determination of molecular weight by gel permeation chromatography (GPC):

[0217] The sample is prepared by dissolving 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. Upon visual inspection, the sample appears to be completely dissolved in the solvent.

[0218] The prepared sample was analyzed using two 300 x 7.5 mm polypore columns (manufactured by Agilent Technologies), a Waters 2695 chromatographic system, a tetrahydrofuran mobile phase and refractive index detection. The sample was filtered through a 0.45 µm nylon filter before being injected into the liquid chromatograph. The calibration standards used were the Easi Vial narrow polystyrene (PS) standards from Agilent Technologies.

[0219] Polystyrene standards ranging from 2,520,000 to 162 Daltons were used for calibration.

[0220] 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 different molecular weights was done using the Win GPC Unichrom 81 program.

[0221] Determination of melting point by differential scanning calorimetry (or DSC)

[0222] This method describes the general procedure for determining the melting point of polymers by differential scanning calorimetry. This method is based on ASTM E791 and ASTM D 34182, and the DSC calibration is performed according to ASTM E 9672.

[0223] Copolvmère acrvlate de béhénvle / acrvlate de 2-hvdroxvéthvle (Polymer I ) :

[0224] In a 4-necked flask equipped with a side-blade stirrer, an internal thermometer, two funnels, a reflux condenser, and an extension for two additional necks, 175 g of behenyl acrylate, 25 g of 2-hydroxyethyl acrylate, and 0.4 g of 2,2'-azobis(2-methylbutyronitrile) (Akzo Nobel) were added to 40 g of isopropanol for 60 minutes at 80 °C, with stirring after removing oxygen from the system by purging with nitrogen for 20 minutes. The mixture was stirred at 80 °C for 3 hours. The solvent was then removed by vacuum distillation, and 1 g of dilauryl peroxide was added, and the reaction was continued for 60 minutes at 110 °C. This step was repeated. The mixture was then cooled to 90 °C and A jet of demineralized water was added and then the mixture was shaken. The water was removed by vacuum distillation.

[0225] Molecular weight: Mn = 7300 g / mol, Mw = 21000, Mw / Mn = 2.8

[0226] Melting point: 65 °C

[0227] Stearyl acrylate / 2-hydroxyethyl acrylate copolymer (Polymer 2):

[0228] In a 4-necked bottle equipped with a side-blade stirrer, a thermometer Internally, two funnels, a reflux condenser, and an extension for two additional necks, 155 g of stearyl acrylate, 45 g of 2-hydroxyethyl acrylate, and 0.4 g of 2,2'-azobis(2-methylbutyronitrile) (Akzo Nobel) were added to 50 g of isopropanol for 90 minutes at 80 °C under stirring after removing oxygen from the system using nitrogen purging for 20 minutes. The mixture was stirred at 80 °C for 3 hours. The solvent was then removed by vacuum distillation, and 1 g of dilauryl peroxide was added, and the reaction was continued for 60 minutes at 125 °C. This step was repeated. The mixture was then cooled to 90 °C, and a stream of demineralized water was added, followed by stirring. The water was removed by distillation under empty.

[0229] Molecular weight: Mn = 7500 g / mol, Mw = 19000, Mw / Mn = 2.6

[0230] Melting point: 49 °C

[0231] Examples of formulations

[0232] Comparative examples 1 and 2

[0233] Compositions 1 and 2 are prepared from the ingredients indicated in the table below, the quantities of which are expressed as % by weight of raw material (RM) in relation to the total weight of the composition. [Tableauxô] Phase Ingrédients Compositio n 1 (Hors invention) Compositio n 2 (Invention) Al EAU QSP 100 QSP 100 Al Conservateurs QS QS Al TRISODIUM ETHYLENEDIAMINE DI- SUCCINATE 0,3 0,3 Al PEG-8 4 4 Al DIPROPYLENE GLYCOL 4 4 Al ACRYLATES COPOLYMER Carbopol Aqua SF1 de Lubrizol 2 2 A2 TRIETHANOLAMINE QS pH 6,7 QS pH 6,7 A3 TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID Mexoryl SX de Noveal 1 1 B BUTYL METHOXYDIBEN- ZOYLMETHANE Parsol 1789 de DSM Nutritional products 2 2 B PENTAERYTHRITYL TETRA- DLT-BUTYL HYDROXYHYDRO- CINNAMATE Tinogard TT de BASF - 0,1 B ETHYLHEXYL SALICYLATE Neo Heliopan OS de Symrise 5 5 B ETHYLHEXYL TRIAZONE Uvinul T150 de BASF 5 5 B DROMETRIZOLE TRISILOXANE Mexoryl XL de Novéal 2 2 B DIETHYLAMINO HYDROXYBENZOYL HEXYL BENZOATE Uvinul A+ de BASF 1 1 B BIS-ETHYLHEXYLOXYPHENOL ME- THOXYPHENYL TRIAZINE 4,5 4,5 Tinosorb S from BASF B DIISOPROPYL SEBACATE Dub Dis from Sterinerie Dubois 8 8 B DIISOPROPYL ADIPATE Dub Dipa from Stearine Dubois 4 4 B C12-22ALKYL ACRYLATE / HYDROXYETHYLACRYLATE COPOLYMER (polymer 1 previously synthesized) 2.5 2.5 B Compound 25 1 1 C ACRYLATES / C10-30 ALKYL ACRYLATE CROSSPOLYMER Pemulen TRI from Lubrizol 0.15 0.15 C SODIUM POLYACRYLATE Cosmedia SP from BASF 0.2 0.2 D WATER 10 10 E SILICA 1 1 E ALUMINUM STARCH OCTENYL-SUCCINATE 2 2 F ALCOHOL DENAT. 5 5

[0234] Method of preparing the compositions:

[0235] Phase A1 is prepared by mixing all the ingredients, then phase A2 is added for neutralization and gel formation. Phase A3 is then added. This entire preparation of phase A, which will be referred to hereafter as phase A, is carried out by heating at 65 °C and stirring with paddles (50 rpm).

[0236] Phase B is prepared by mixing all the ingredients and heating to 80 °C under magnetic stirring until a clear and homogeneous phase is obtained.

[0237] Emulsification is carried out by dispersing phase B in phase A at 65 °C under vigorous 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 gradually lowered to room temperature while maintaining the same stirring speed until the end. At around 55 °C, the thickeners from phase C are added (5 minutes), followed by phase D (5 minutes), and the fillers from phase E starting at 35 °C. Finally, the alcohol from phase E is added once the mixture has returned to room temperature.

[0238] Results:

[0239] Once prepared, compositions 1 and 2 are each spread onto 6 Europlast PMMA plates at a rate of 2.0 to 2.1 mg / cm² (corresponding to between 16 and 17 mg over 8 cm²). 3 of the 6 plates are then exposed under a Suntest (HERAEUS) with a UV dose of 43.2 J / cm² at a temperature of 40°C, while the others are stored at the same temperature in the dark.

[0240] After irradiation, the residual levels in 2-cyano{ 3-[(3-methoxypropyl)amino]-cyclohex-2-en-l-ylidene]ethanoate of 2-ethoxyethyl in each of the 6 plates are measured by classical HPLC chromatography methods.

[0241] The residual fraction after irradiation expressed in % corresponds to the ratio of the average residual content of the ingredient contained on the 3 plates that have been exposed to the average residual content of the 3 plates that have not been exposed for the same composition.

[0242] The results obtained are summarized in the table below. [Paintings?] Residual fraction after irradiation Composition 1 (Not part of the invention) Composition 2 (Invention) 2-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en-1-ylidene} 2-ethoxyethyl ethanoate (compound 25) 69% ± 0.8% 76% ± 0.5%

[0243] These results show that composition 2 according to the invention has a residual fraction of merocyanine compound substantially greater than that of comparative composition 1, which shows that in the presence of di-t-butyl pentaerythrityl tetrahydroxycinnamate, the merocyanine compound exhibits better photostability with respect to UV radiation.

Claims

Claims

1. Cosmetic or dermatological composition comprising: (a) at least one merocyanine corresponding to the following formula (3), as well as their isomeric geometric forms, in particular E / E or E / Z: [Formula 3] in which: A is -O- or -NH; R is a CrC22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted by one or more O; and b) di-t-butyl pentaerythrityl tetrahydroxycinnamate.

2. Composition according to claim 1 in which the merocyanines of formula (3) are chosen from the following compounds, as well as their isomeric geometric forms, in particular E / E or E / Z: [Tables 1] 14 H .._O ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene}ethanoate 15 £ H ,□ CU .O. au / L (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylide ne}ethanamide 25 H '1 " ° r j u 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene]ethanoate 27 * H 2-methylpropyl (2Z)-cyano{3-[( ohex-2-en-l-yli Z DX X ' ' 3-methoxypropyl)amino]cycl iene]ethanoate 29 1 [t 2-butoxyethyl (2Z)-cyano{3-[( ohex-2-en-l-yli X „0, x-x 3-methoxypropyl)amino]cycl iene]ethanoate 31 CL (X ...O, § H > 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene]ethanoate 37 H '1 1 . j 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene]ethanoate [Revendication 3] Composition according to any one of claims 1 and 2 in which the merocyanine of formula (3) is 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylidene}ethan oate (25) in its geometric E / Z configuration of the following structure: [formula 25]

4.

5. HI AX >£■' y* [ ] "■ N and / or in its geometric configuration E / E of the following structure: [formula 25bis] rX HJH f O Composition according to any one of claims 1 to 3 in which the di-t-butyl pentaerythrityl tetrahydroxycinnamate is present in a content ranging from 0.01% to 2.5% by weight, preferably from 0.05% to 1.5% by weight, more preferably from 0.1% to 0.3% by weight relative to the total weight of the composition. Composition according to any one of claims 1 to 4 comprising at least one polymer comprising monomeric units of formulas (A) and (B): [formula A] [formula B] in which: RI, independently of one another, is chosen from alkyl or alkylene radicals, and at least 60% by weight of the RI groups are radicals chosen from stearyl and behenyl radicals, the weight percentage 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 of the total weight of the polymer, the polymer having a number-average molecular weight Mn ranging from 2,000 to 9,000 g / mol.

6. Composition according to claim 5 in which in the additional polymer RI consists of an alkyl radical, preferably a C16-C22 alkyl radical, and more preferably a behenyl or stearyl radical.

7. Composition according to any one of claims 5 and 6 in which in the additional polymer at least 70% by weight of the RI groups are behenyl or stearyl radicals, preferably at least 80% by weight, more preferably at least 90% by weight.

8. Composition according to any one of claims 5 to 7 in which in the additional polymer all the RI groups are stearyl or behenyl radicals.

9. Composition according to any one of claims 5 to 8 in which in the additional polymer said weight ratio ranges from 1:15 to 1:1, preferably ranges from 1:10 to 1:

4.

10. Composition according to any one of claims 5 to 9 in which the additional polymer has a number average molecular weight Mn ranging from 5,000 to 9,000 g / mol.

11. Composition according to any one of claims 5 to 10 in which the additional polymer has a melting temperature ranging from 40°C to 70°C, and preferably ranging from 45°C to 67°C.

12. Composition according to any one of claims 5 to 11 in which in the additional polymer at least 60% by weight of the RI groups are stearyl radicals, and said additional polymer has a melting point ranging from 40 to 60°C, and preferably ranging from 45 to 55°C.

13. Composition according to any one of claims 5 to 12 in which in the additional polymer at least 60% by weight of the RI groups are behenyl radicals, and said additional polymer has a melting point ranging from 60°C to 70°C, and preferably ranging from 63°C to 67°C.

14. Composition according to any one of claims 1 to 13 further comprising one or more additional UV filters, preferably one or more compounds derived from dibenzoylmethane chosen from those of the following formula, and / or mixtures thereof: [formula 6] R, QO v Rs h4 in which: Ri, R4, R5 and R6 represent, independently of each other, 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 each other, 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 bonds C-R2 and C-R3 a 5- or 6-membered heterocycle optionally substituted by a linear or branched C1-C4 hydrocarbon chain.

15. Composition according to claim 14 in which the dibenzoylmethane derivative(s) are chosen 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'-methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4'-methoxy-dibenzoylmethane, l-(4-tert-butylphenyl)-3-(2-hydroxyphenyl)-propane-l,3-dione, l-(4-methoxy-l-benzofuran-5-yl)-3-phenyl-propane-l,3-dione; preferably chosen, alone or in a mixture, from 4-tert-butyl-4'-methoxydibenzoylmethane and / or 4-isopropyldibenzoylmethane; preferentially chosen from 4-tert-butyl-4'-methoxydibenzoylmethane.

16. A composition according to any one of claims 1 to 15 comprising 4-tert-butyl-4'-methoxydibenzoylmethane.

17. Non-therapeutic cosmetic process for the care and / or makeup of a keratin material comprising the application to the surface of said keratin material of at least one composition as defined in any one of claims 1 to 16.

18. Use of di-t-butyl pentaerythrityl tetrahydroxycinnamate for photostabilizing a merocyanine as defined in any one of claims 1 to 3.