Cosmetic or dermatological composition comprising merocyanine and dipropylene glycol

Abstract

A cosmetic or dermatological composition comprising a merocyanin and dipropylene glycol. 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 groups; and b) dipropylene glycol. The present invention also relates to a non-therapeutic cosmetic process for the care and / or makeup of a keratinous material comprising the application to 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 dipropylene glycol

[0001] The present invention relates to a cosmetic or dermatological composition comprising at least one merocyanine of formula (3) which will be defined in detail below and dipropylene glycol.

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

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

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

[0006] It is also known that UV-A rays with a wavelength between 320 and 400 nm penetrate deeper into the skin than UV-B rays. UV-A rays cause immediate and persistent browning of the skin. Daily exposure to UVA rays, even for short periods, under normal conditions can lead to a degradation of collagen and elastin fibers which results in a change in the micro-relief of the skin, the appearance of wrinkles and irregular 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] Many photo-protective compositions have been proposed to date to remedy the effects induced by UVA and / or UVB radiation. They contain generally organic UV filters and / or inorganic UV filters that work according to their own chemical nature and properties by absorbing, reflecting, or scattering UV radiation. They generally contain mixtures of fat-soluble organic filters and / or water-soluble UV filters combined with metal oxide pigments such as titanium dioxide or zinc oxide.

[0009] Many cosmetic compositions intended to limit the darkening of the skin, improve the color and homogeneity of the complexion have been proposed to date. It is well known in the field of sunscreens that such compositions can be obtained by using UV filters, and in particular UVB filters. Some compositions may also contain UVA filters. This filtering system must cover UVB protection in order to limit and control the neosynthesis of melanin promoting overall pigmentation, but must also cover UVA protection in order to limit and control the oxidation of the already existing melanin leading to the darkening of the skin color.

[0010] However, it is extremely difficult to find a composition containing a particular combination of UV filters which would be specially adapted to the photoprotection of the skin and particularly to 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 after on already pigmented skin in order to not increase either the pigment load in melanin or the structure of the melanin already present within 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 solar radiation filtering power, the desired photoprotection compounds must also have good cosmetic properties, good solubility in common solvents and in particular in fatty substances such as oils, as well as good photostability 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 development by a system filtering UV over the entire UV spectrum.

[0014] Among all the compounds that have been recommended for this purpose, an interesting family of UV filters has been proposed which consists of carbonaceous merocyanine derivatives which is described in patent US4195999, application WO2004 / 006878 and document IP COM Journal 4 (4), 16 N°IPCOM000011179D published on 04 / 03 / 2004. These compounds have very good filtration properties in long UVA radiation but have a poorly satisfactory solubility in usual solvents, both in aqueous phase and in fatty phase, and an unsatisfactory photo-stability for certain merocyanines.

[0015] In order to search for other merocyanines having better solubility in usual solvents and better photostability, application WO2013 / 011094 proposed merocyanines comprising polar groups consisting of hydroxyl and ether functions which show good long UVA filtration efficiency. However, the solubility of these particular merocyanines is not yet fully satisfactory, and often requires a tedious formulation process. Furthermore, the large quantities of solvent required to solubilize this type of merocyanine can lead to cosmetic problems such as a sticky and greasy effect upon application.

[0016] There therefore remains a need to improve the solubility of these merocyanines in cosmetic compositions, in particular photo-protective formulations, both in the aqueous phase and in the fatty phase, while obtaining good cosmeticity.

[0017] The Applicant has surprisingly discovered that by using dipropylene glycol, it is possible to significantly improve the solubility of these merocyanines both in an aqueous phase and in a fatty phase. This discovery is the basis of the present invention.

[0018] Thus, in accordance with one of the objects of the present invention, there is now provided a cosmetic or dermatological composition comprising at least one merocyanine of formula (3) which will be defined in detail below and dipropylene glycol.

[0019] Furthermore, there also remains the need to improve the solubility of merocyanines in the presence of organic filters. Indeed, the addition of additional filters can destabilize compositions comprising a merocyanine.

[0020] The Applicant has surprisingly discovered that by using dipropylene glycol, it is possible to significantly improve the solubility of these merocyanines in an aqueous phase or in a fatty phase, even in the presence of additional organic UV filters.

[0021] The Applicant has also discovered that the use of dipropylene glycol makes it possible to obtain good cosmeticity of the composition comprising the merocyanines, the latter being in particular non-greasy and non-sticky.

[0022] The present invention also relates to a non-therapeutic cosmetic process for caring for and / or making up a keratin material comprising the application to the surface of said keratin material of at least one composition according to the invention as defined above.

[0023] It also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and / or improving the color and / or uniformity of the complexion comprising the application to the surface of the keratin material of at least one composition as defined above.

[0024] It also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratin material comprising the application to the surface of the keratin material of at least one composition as defined above.

[0025] The present invention also relates to the use of dipropylene glycol for solubilizing a merocyanine of formula (3) as defined below, in particular for solubilizing these molecules in the fatty phase and / or in the aqueous phase.

[0026] Other characteristics, aspects and advantages of the invention will appear on reading the detailed description which follows.

[0027] The composition according to the invention is intended for topical application and therefore contains a physiologically acceptable medium. Here, the term “physiologically acceptable medium” means a medium compatible with keratin materials.

[0028] In the context of the present invention, the term "keratin material" is understood to mean in particular the skin, the scalp, the keratin fibers such as the eyelashes, the eyebrows, the hair, and the body hairs, the nails, the mucous membranes such as the lips, and more particularly the skin and the mucous membranes (body, face, eye contour, eyelids, lips, preferably body, face and lips).

[0029] In what follows, and unless otherwise indicated, the limits of a domain of values ​​are included in this domain, in particular in the expressions “between” and “ranging from ... to ...”.

[0030] Furthermore, the expressions “at least one” and “at least” used in the present description are respectively equivalent to the expressions “one or more” and “greater than or equal”.

[0031] By "prevent" or "prevention", according to the invention, is meant the fact of 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 keratin material. MEROCYANINES

[0032] According to the present invention, a family of merocyanines corresponding to the following formula (3) will be used 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 alkinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted by one or more O.

[0033] The merocyanine compounds of the invention may be in their geometric isomeric forms E / E-, E / Z-: [formula 3]

[0034] Even more preferred compounds of formula (3) are those where: A is -O-; R is Cr-C22 alkyl, which may be interrupted by one or more O's.

[0035] Among the compounds of formula (3), those chosen from the following group and their isomeric geometric forms, in particular E / E-, E / Z-, will be used more particularly: [Tables 1] 14 0.^0 ^ / X -k ^X U *N ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate 15 OXA / x f H "ï kj (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylide ne}ethanamide 25 f 1 A 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanoate 27 CL CX-CL Jx j H f [ 1 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)ammo]cycl ohex-2-en-1 -ylidene} ethanoate 29 k CL'Ox x^x~^x | ■■ 0 ■ r ] 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

[0036]

[0037] According to a more particularly preferred embodiment of the invention, the 2-ethoxyethyl compound will be used (2Z)-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en- l-ylidene]ethanoate (25) in its E / E and / or E / Z geometric configuration. The E / Z form has the following structure: [formula 25]

[0038] The E / E form has the following structure: [formula 25bis]

[0039] The filtering merocyanines in accordance with the invention may be present in the compositions according to the invention in a concentration ranging from 0.1% to 15% by weight, and 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.

[0040] 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 title “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.

[0041] 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, which is entitled “A cyclic me-rocyanine UV-A absorber: mechanism of formation and crystal structure”, and represented below, for compounds of formula (3): [formula 4] And more particularly for compound 25 described in table 1: [formula 5] DIPROPYLENE GLYCOL

[0042] The composition in accordance with the invention comprises dipropylene glycol.

[0043] According to a particular embodiment, dipropylene glycol is present in the composition of the present invention in an amount of between 0.1 and 99%,

[0044] in particular between 0.5 and 50%, preferably between 1 and 25%, and even more preferably between 1 and 10%, for example between 1 and 5% by weight of the total weight of the composition. ADDITIONAL ACRYLIC POLYMER 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] 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 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 of units A and B is at least 95% by weight of the total weight of the polymer.

[0045] Preferably, RI consists of alkyl radicals, preferably C16-C22 alkyl radicals, and more preferably stearyl radicals (C18) or behenyl radicals (C22).

[0046] 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 less than 90% by weight.

[0047] According to a preferred embodiment, all the RI groups are behenyl radicals.

[0048] According to another preferred embodiment, all the RI groups are stearyl radicals.

[0049] Preferably, said weight ratio ranges from 1:15 to 1:1, preferably from 1:10 to 1:4.

[0050] Advantageously, the polymer units present in the polymer consist of the units (A) and (B) described above.

[0051] 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 with the gel permeation chromatography method, for example according to the method described in the example below.

[0052] Preferably, the polymer has a melting temperature ranging from 40°C to 70°C, and preferably ranging from 45°C to 67°C. The melting temperature is measured by differential scanning calorimetry (or DSC: Differential Scanning Calorimetry), for example according to the method described in the example below.

[0053] 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.

[0054] 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 ranging from 63°C to 67°C.

[0055] 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 above, and 2-hydroxy ethyl acrylate.

[0056] The polymerization can be carried out according to known methods, such as solution or emulsion polymerization.

[0057] The polymerization is for example described in document US 2007 / 0264204.

[0058] 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 still ranging from 0.2 to 3% by weight. ALKYL OR ALKYLENE CARBONATES

[0059] According to another particular embodiment, the composition in accordance with the invention comprises at least one alkyl or alkylene carbonate.

[0060] According to a preferred embodiment, the alkylene carbonate(s) are in particular chosen from those of the following formula (6): [formula 6] in which

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] R' denotes a hydrogen atom, a linear or branched C1-C6 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; R” represents a hydrogen atom, a linear or branched C1-C6 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; m is 1, 2 or 3. Preferably, the radical R' represents a hydrogen atom, a linear or branched CrC4 alkyl radical, a linear or branched Ci-C2 hydroxyalkyl radical. R” represents a hydrogen atom, a linear or branched C1-C2 alkyl radical, a linear or branched C1-C2 hydroxyalkyl radical Preferably m is 1. As particularly advantageous examples of alkylene carbonates, mention may be made of compounds for which the radical R' represents a hydrogen atom (corresponding to ethylene carbonate), a methyl group (corresponding to propylene carbonate), ethyl (corresponding to 1,2-butylene carbonate), hydroxymethyl (R'= -CH2OH; corresponding to glycerin carbonate). Preferably, the alkylene carbonate used is propylene carbonate. According to another embodiment, the alkyl carbonate(s) are in particular chosen from those of the following formula (7): [formula 7] R'-O-CO-OR” in which: R' denotes an atom, a linear or branched C1-C5 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; R” represents a linear or branched C1-C5 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; the sum of the carbons of R' and R'' ranging from 2 to 6. Preferably, the radical R' represents a linear C1-C3 alkyl radical, a radical linear C1-C2 hydroxyalkyl.

[0068] R' ' represents a linear C1-C3 alkyl radical, a linear C1-C2 hydroxyalkyl radical.

[0069] More particularly, mention may be made of diethyl carbonate and dipropyl carbonate.

[0070] The carbonates according to the invention are preferably alkylene carbonates, and more particularly propylene carbonate.

[0071] The alkyl or alkylene carbonate(s) are generally present in the compositions according to the invention at concentrations ranging from 0.1 to 98% by weight, preferably from 0.5 to 50% by weight, more preferably from 1 to 20% by weight, and even more particularly from 1 to 10% by weight, for example from 1 to 6% by weight relative to the total weight of the composition. HYDROTROPIC

[0072] According to a particular embodiment of the invention, the composition comprises at least one hydrotrope.

[0073] Thus, a composition according to the invention may comprise at least one hydrotrope chosen from nicotinamide, caffeine, salts of salicylic acid, sodium salt of pyroglutamic acid (sodium PCA), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), sodium butyl monoglycolsulfate (NaBMGS), 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof.

[0074] According to a preferred embodiment, a composition according to the invention comprises at least one hydrotrope chosen from nicotinamide, caffeine and their mixtures. In particular, such a composition may further comprise at least one additional hydrotrope selected from salts of salicylic acid, sodium salt of pyroglutamic acid (sodium PCA), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), sodium butyl monoglycolsulfate (NaBMGS), 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof.

[0075] According to an alternative embodiment, a composition according to the invention comprises at least one hydrotrope chosen from nicotinamide, caffeine and one of their mixtures combined with at least one salicylic acid salt.

[0076] The salts of salicylic acid may in particular be chosen from sodium salicylate, lysine salicylate, arginine salicylate, magnesium salicylate, and mixtures thereof.

[0077] Preferably, the salt of salicylic acid is sodium salicylate.

[0078] According to a preferred embodiment, a composition according to the invention comprises at least nicotinamide.

[0079] According to a particular embodiment, a composition according to the invention comprises nicotinamide and sodium salicylate.

[0080] When they are present in the composition according to the invention, the hydrotrope(s) are present in an amount effective for solubilizing in water the merocyanine(s) of formula (3) as described above.

[0081] The amount of hydrotrope(s) according to the invention present in the compositions according to the invention may range from 0.1% to 20% by weight, in particular from 0.1% to 10% by weight, preferably from 0.5% to 10% by weight, relative to the total weight of the composition.

[0082] In particular, the mass ratio of merocyanine(s) of formula (3) / hydrotrope(s) according to the invention, of a composition according to the invention ranges from 0.1 to 8, preferably from 0.2 to 5, in particular from 0.5 to 3, and more preferably from 0.8 to 1.5.

[0083] According to a particular embodiment, a composition according to the invention comprises at least two distinct hydrotropes chosen from nicotinamide, caffeine, and sodium salicylate, and the mass ratio of merocyanine(s) of formula (3) / hydrotropes of a composition according to the invention varies from 0.1 to 5, preferably from 0.2 to 3, in particular from 0.4 to 1, and more preferably from 0.4 to 0.6.

[0084] According to a particular embodiment, a composition according to the invention comprises two distinct hydrotropes, preferably nicotinamide and caffeine and the mass ratio between these two hydrotropes varies from 0.2 to 5, in particular from 0.5 to 3, and more preferably from 0.8 to 1.2. FAT PHASE

[0085] The composition in accordance with the invention may comprise at least one fatty phase.

[0086] For the purposes of the invention, the term “fatty phase” means a phase comprising at least at least one 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.

[0087] According to a particular embodiment, the composition according to the invention comprises at least one oil.

[0088] Oil means any fatty substance in liquid form at room temperature (20-25°C) and atmospheric pressure (760 mm Hg).

[0089] The fatty phase may comprise in particular 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.

[0090] For the purposes of the present invention, the term “silicone oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.

[0091] The term "hydrocarbon oil" means an oil containing mainly hydrogen and carbon atoms and possibly one or more heteroatoms, in particular nitrogen and oxygen. Thus, these oils may in particular contain one or more carboxy, ester, ether or hydroxy functions.

[0092] The term “fluorinated oil” means an oil comprising at least one fluorine atom.

[0093] For the purposes of the invention, the term "volatile oil" means an oil capable of evaporate on 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).

[0094] By "non-volatile oil" is meant an oil remaining on the skin or keratin fiber at room temperature and atmospheric pressure for at least several hours and in particular having a vapor pressure of less than 103 mm Hg (0.13 Pa). Hydrocarbon oils

[0095] The composition in accordance with the invention may comprise at least one ester of C2-C22 di or tricarboxylic acid and C1-C24 alcohols.

[0096] The C2-C22 di or tricarboxylic acids are in particular chosen from citric acid, malic acid, malonic acid, succinic acid, adipic acid, maleic acid, fumaric acid, tartaric acid, isocitric acid and mixtures thereof. Preferably the acids are citric acid and adipic acid, and even more preferably it is citric acid.

[0097] C1-C24 alcohols are not oxyalkylenated. They can be aliphatic, cyclic or aromatic, having from 1 to 24 carbon atoms. They are in particular chosen from phenol, benzyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, methanol, ethanol, propanol, n-butanol, t-butanol, pentanol, hexanol. Preferably, the alcohol(s) are C1-C6 and may be chosen from methanol, ethanol, propanol, n-butanol, t-butanol, pentanol, hexanol, and even more preferably it is ethanol.

[0098] The ester(s) of C2-C22 di- or tricarboxylic acid and C1-C24 alcohols may be mono- or poly-esterified.

[0099] By mono-esterified is meant that only one of the two or three carboxylic acid functions is esterified. By poly-esterified is meant that at least two carboxylic acid functions are esterified.

[0100] The di or tricarboxylic acid can be esterified by several different alcohols. Preferably, it is esterified by a single alcohol.

[0101] According to a particular embodiment of the invention, the composition comprises at least one ester of C3-C22 tricarboxylic acid and C1-C24, preferably C1-C6, alcohols. This or these esters may be mono-, di- or tri-esterified.

[0102] By mono-esterified is meant that only one of the three carboxylic acid functions is esterified. By diesterified is meant that two of the three carboxylic acid functions are esterified. By tri-esterified is meant that all three carboxylic acid functions are esterified.

[0103] According to a particular embodiment of the invention, the ester(s) of C3-C22 tricarboxylic acid and C1-C6 alcohols are tri-esterified.

[0104] According to a particular embodiment of the invention, the ester(s) of C3-C22 tricarboxylic acid and C1-C6 alcohols are chosen from the compounds of the following formula (8): (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, saturated or unsaturated, aliphatic, cyclic or aromatic hydrocarbon group having from 1 to 6 carbon atoms; R represents a hydrogen atom or a hydroxyl radical.

[0105] According to a preferred embodiment, RI, R2 and R3 represent, independently of one another, a hydrogen atom or a linear or branched, substituted or unsubstituted, preferably unsubstituted, C1-C6 alkyl radical, and in particular a radical chosen from methyl, ethyl, propyl, n-butyl, t-butyl, pentyl and hexyl radicals. Preferably, RI, R2 and R3 are chosen independently of one another from a hydrogen atom and methyl, ethyl, propyl, n-butyl and t-butyl radicals.

[0106] According to a preferred embodiment of the invention, the radicals R1, R2 and R3 are identical and are chosen from C1-C6 alkyl radicals, preferably C1-C4, and even more preferably they are ethyl radicals.

[0107] According to a preferred embodiment of the invention, R represents a radical hydroxyl.

[0108] According to a particular embodiment of the invention, the ester of tricarboxylic acid and C1-C6 alcohols has the following formula: [Formula 9]

[0109] As an example of an ester of C3-C22 tricarboxylic acid and C1-C6 alcohols of formula (10) and INCI name TRIETHYL CITRATE, mention will be made of that which is marketed under the name CITROFOL AI EXTRA by the company JUNG-BUNZLAUER.

[0110] As non-volatile hydrocarbon oils which can be used according to the invention, mention may also be made of: (i) hydrocarbon oils of vegetable origin such as glyceride triesters which are generally triesters of fatty acids and glycerol whose fatty acids may have chain lengths varying from C4 to C24, the latter being able to be linear or branched, saturated or unsaturated; These oils include wheat germ, sunflower, grape seed, sesame, corn, apricot, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, and musk rose; or caprylic / capric acid triglycerides 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 from 10 to 40 carbon atoms; (iii) linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam, squalane, and mixtures thereof; (iv) synthetic esters such as oils of formula RCOOR' in which R represents the residue of a linear or branched fatty acid containing from 1 to 40 carbon atoms and R' represents a hydrocarbon chain, in particular a branched chain, containing from 1 to 40 carbon atoms provided that R + R' is > 10, such as for example Purcellin oil (cetostearyl octanoate), isopropyl myristate, palmitate isopropyl, C12-C15 alcohol benzoate such as the product sold under the trade name "Finsolv TN®" or "Witconol TN®" by the company WITCO or "TEGOSOFT TN®" by the company EVONIK GOLDSCHMIDT, 2-ethylphenyl benzoate such as the commercial product sold under the name "X-TEND 226®" by the company ISP, isopropyl lanolate, hexyl laurate, dii-isopropyl adipate, isononyl isononanoate, oleyl erucate, 2-ethylhexyl palmitate, isostearyl isostearate, diisopropyl sebacate such 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 such as those sold under the name COSMACOL ETI® by the company ENICHEM AUGUSTA INDUSTRIALE as well as linear C14-C15 dialkyl tartrates such as those sold under the name COSMACOL ETL® by the same company; acetates; (v) fatty alcohols which are liquid at room temperature with a branched and / or unsaturated carbon chain having from 12 to 26 carbon atoms such as octyl dodecanol, isostearyl alcohol, oleyl 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.

[0111] Among the non-volatile hydrocarbon oils that can be used according to the invention, preference will be given more particularly to 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. Preferably, the non-volatile hydrocarbon oils are chosen from diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate and dicaprylyl carbonate.

[0112] As volatile hydrocarbon oils which can be used according to the invention, mention may in particular be made of hydrocarbon oils having from 8 to 16 carbon atoms, and in particular branched C8-Ci6 alkanes such as C8-Ci6 isoalkanes of petroleum origin (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, branched C8-Ci6,1e neo- isohexyl pentanoate, and mixtures thereof.

[0113] Mention may also be made of the alkanes described in the patent applications of the company Cognis WO 2007 / 068371, or WO2008 / 155059 (mixtures of distinct alkanes and different by at least one carbon). These alkanes are obtained from fatty alcohols, themselves obtained from coconut or palm oil, and mention may be made of the mixtures of n-undecane (Cn) and n-tridecane (Cn) obtained in examples 1 and 2 of application WO2008 / 155059 of the company Cognis. Mention may also be made of n-dodecane (Ci2) and n-tetradecane (Ci4) sold by Sasol respectively under the references PARAFOL 12-97 and PARAFOL 14-97®, as well as their mixtures.

[0114] Other volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the name Shell Soit® by the company SHELL, may also be used. According to one embodiment, the volatile solvent is chosen from volatile hydrocarbon oils having from 8 to 16 carbon atoms and their mixtures. Silicone oils

[0115] The non-volatile silicone oils may be chosen in particular from non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes comprising alkyl or alkoxy groups, pendant and / or at the end of the silicone chain, groups each 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 silicates.

[0116] As volatile silicone oils, mention may be made, for example, of volatile linear or cyclic silicone oils, in particular those having a viscosity < 8 centistokes (8 106 m2 / 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. As volatile silicone oil which may be used in the invention, mention may be made in particular of octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane and mixtures thereof.

[0117] A fatty phase according to the invention may further comprise, mixed with or dissolved in the oil, other fatty substances.

[0118] Another fatty substance which may be present in the fatty phase may be, for example: - a fatty acid chosen from fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; - a wax chosen from waxes such as lanolin, beeswax, Camauba or Candellila wax, rice bran wax, paraffin wax, lignite wax or microcrystalline wax, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; - a gum chosen from silicone gums (dimethiconol), - a pasty compound, such as polymeric or non-polymeric silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives, - and their mixtures.

[0119] Preferably, the overall fatty phase, including all the lipophilic substances other than the lipophilic filters of the composition capable of being 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

[0120] The composition in accordance with the invention may comprise at least one aqueous phase.

[0121] The aqueous phase contains water, and optionally other organic solvents soluble or miscible in water.

[0122] An aqueous phase suitable for the invention may comprise, for example, a water chosen from a natural spring water, such as La Roche-Posay water, Vittel water, Saint Gervais Mont Blanc water, or Vichy water, or a floral water. According to a particular form of the invention, the overall aqueous phase, including all the hydrophilic substances other than the hydrophilic filters 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

[0123] Additional UV filters

[0124] The compositions according to the invention may additionally contain one or more complementary UV filters chosen 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.

[0125] By "hydrophilic UV filter" is meant any organic or inorganic cosmetic or dermatological compound filtering UV radiation capable of being completely dissolved in the molecular state in a liquid aqueous phase or of being solubilized in colloidal form (for example in micellar form) in a liquid aqueous phase.

[0126] By "lipophilic filter" is meant any organic or inorganic cosmetic or dermatological compound filtering UV radiation capable of being completely dissolved in the molecular state in a liquid fatty phase or of being solubilized in the form colloidal (e.g. in micellar form) in a liquid fatty phase.

[0127] By "insoluble UV filter" is meant any organic or inorganic cosmetic or dermatological compound filtering UV radiation having a solubility in water 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 the company DYNAMIT NOBEL. This solubility, achieved at 70°C, is defined as the quantity of product in solution in the solvent at equilibrium with an excess of solid in suspension after returning to room temperature. It can easily be evaluated in the laboratory.

[0128] The complementary organic UV filters are in particular chosen from cinnamic compounds; anthranilate compounds; salicylic compounds, dibenzoylmethane compounds, benzylidene camphor compounds; benzophenone compounds; [3,[3-diphenylacrylate] compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds in particular those cited in patent US5624663; 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 US5,237,071, 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;dimers derived from α-alkylstyrene such as those described in patent application DE19855649; 4,4-diarylbutadienes compounds as described in applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EPI 133980 and EPI33981 and mixtures thereof.;

[0129] Examples of organic photoprotective agents include those designated below by their INCI name.

[0130] Cinnamic compounds: Ethylhexyl Methoxycinnamate sold in particular 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.

[0131] Dibenzoylmethane compounds: Butyl Methoxydibenzoylmethane sold in particular under the trade name PARSOL 1789 ® by DSM Nutritial Products, Isopropyl Dibenzoylmethane.

[0132] Para-aminobenzoic compounds: PABA, Ethyl PABA, Ethyl Dihydroxypropyl PABA, Ethylhexyl Dimethyl PABA sold in particular under the name “ESCALOL 507®” by ISP, Glyceryl PABA, PEG-25 PABA sold under the name “UVINUL P 25®” by BASF.

[0133] Salicylic 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.

[0134] Compounds [3.[3-diphenylacrylate: Octocrylene sold in particular under the trade name “UVINUL N 539®” by BASF, Etocrylene, sold in particular under the trade name “UVINUL N 35®” by BASF.

[0135] 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, 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyl sold under the trade name “UVINUL A Plus ®” or in mixture with octylmethoxycinnamate under the trade name “UVINUL A Plus B®” by the company 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 at 2 pm) which can be obtained for example according to the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in the form of an aqueous dispersion.

[0136] Benzvlidene 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.

[0137] Phenyl benzimidazole compounds: Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name “EUSOLEX 232®” by MERCK.

[0138] Bis-benzoazolyl compounds: Disodium Phenyl Dibenzimidazole Tetra-sulfonate sold under the trade name “NEO HELIOPAN AP®” by Haarmann and REIMER.

[0139] Phenyl benzotriazole compounds: Drometrizole Trisiloxane sold under the name “Silatrizole®” by RHODIA CHIMIE.

[0140] Methylene bis-(hvdroxvphénvl benzotriazole) compounds: Methylene bis-Benzotriazolyl Tetramethylbutylphenol in particular in solid form such as the product sold under the trade name “MIXXIM BB / 100 ®” by FAIRMOUNT CHEMICAL or in the form of an aqueous dispersion of micronized particles having an average particle size which varies from 0.01 to 5 pm and more preferably from 0.01 to 2 pm and more particularly from 0.020 to 2 pm with at least one alkylpolyglycoside surfactant of structure CnH2n+i O(C6Hi0O5)xH in which n is an integer from 8 to 16 and x is the average degree of polymerization of the unit (C6Hi0O5) and varies from 1.4 to 1.6 as described in patent GB-A-2 303 549 in particular sold under the trade name “TINOSORB M®” by BASF or in the form of an aqueous dispersion of micronized particles having an average particle size particles which vary from 0.02 to 2 pm and more preferably from 0.01 to 1.5 pm and more particularly from 0.02 to 1 pm in the presence of at least one mono-(C8-C20)alkyl-ester of poly-glycerol having a degree of polymerization of glycerol of at least 5 such as the aqueous dispersions described in application WO2009 / 063392.,

[0141] Triazine compounds: - 3,3'-(l,4-Phenylene)bis(5,6-diphenyl-l,2,4-triazine), with the INCI name Phenylene Bis-Diphenyl triazine, with the following chemical formula: [formula 10] - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the trade name “TINOSORB S®” by BASF, - Ethylhexyl Triazone sold in particular 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'-amino dineopentyl benzahnalonate)-s-triazine, - 2,4,6-tris-(4'-amino diisobutyl benzahnalonate)-s-triazine, - n-butyl 2,4-bis-(4'-aminobenzoate)-6-(aminopropyltrisiloxane)-s-triazine, - 2,4-bis-(4'-aminobenzalmalonate de dineopentyl)-6-(4'-aminobenzoate de n-butyle)-s-triazine, - symmetrical triazine filters substituted by naphthalenyl groups or polyphenyl groups described in patent US6,225,467, 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 particle size of 0.02 to 3 pm) which can be obtained for example according to the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in the form of an aqueous dispersion, - 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.

[0142] Anthranilic compounds: Menthyl anthranilate sold under the trade name “NEO HELIOPAN MA®” by Symrise.

[0143] Imidazoline compounds: Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate.

[0144] Benzalmalonate compounds: Polyorganosiloxane with benzalmalonate functions such as Polysilicone-15 sold under the trade name “PARSOL SLX ®” by HOFFMANN LA ROCHE.

[0145] 4.4-Diarylbutadiene Compounds: -1,1-dicarboxy(2,2'-dimethyl-propyl)-4,4-diphenylbutadiene.

[0146] Benzoxazole compounds: 2,4-bis-[5-l(dimethylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imi no-l,3,5-triazine sold as Uvasorb K2A® by Sigma 3V.

[0147] The preferred organic filters are chosen from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, Homosalate, Butyl Methoxydibenzoylmethane, 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'-diméthyl-propyl)-4,4-diphénylbutadiène, 2,4-bis-[5-l(diméthylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imin o-l,3,5-triazine, et leurs mélanges.

[0148] Les filtres organiques particulièrement préférés sont choisis parmi : Ethylhexyl Salicylate, Homosalate, Butyl Methoxydibenzoylmethane, Octocrylene, 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyle, 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, et leurs mélanges.

[0149] The inorganic UV filters used in accordance with 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 of less than or equal to 0.5 μm, more preferably between 0.005 and 0.5 μm and even more preferably between 0.01 and 0.2 μm, even better between 0.01 and 0.1 μm, and more particularly between 0.015 and 0.05 μm.

[0150] They can be chosen in particular from titanium, zinc, iron, zirconium, cerium oxides or their mixtures.

[0151] Such coated or uncoated metal oxide pigments are described in particular in patent application EP-A-0 518 773. As commercial pigments, mention may be made of the products sold by the companies SACHTLEBEN PIGMENTS, TAYCA, MERCK and DEGUSSA.

[0152] Metal oxide pigments may be coated or uncoated.

[0153] Coated pigments are pigments which 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.

[0154] The coated pigments are more particularly titanium oxides coated: - with silica such as the product "SUNVEIL®" from the company IKEDA, - silica and iron oxide such as the product "SUNVEIL F®" from the company IKEDA, - 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, - 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, - silica, alumina and alginic acid such as the product "MT-100 AQ®" from the company TAYCA, - 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, - silica and alumina and treated with a 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, - silica, alumina, aluminum stearate and treated with a silicone such as the product "STT-30-DS®" from the company TITAN KOGYO, - silica and treated with a silicone such as the product "UV-TITAN X 195®" from the company SACHTLEBEN PIGMENTS, - 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, - 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, - anatase / rutile TiO2 treated with polydimethylhydrogensiloxane 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) from CRODA, - TiO2 coated with aluminum 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 aluminum hydroxide sold by Daito Kasei Kogyo under the name PFX-5 TiO2 CR-50.

[0155] Mention may also be made of TiO2 pigments doped with at least one transition metal such as iron, zinc, manganese and more particularly manganese. Preferably, said doped pigments are in the form of an oily dispersion. The oil present in the oily dispersion is preferably chosen from triglycerides including those of capric / caprylic acids. The oily dispersion of titanium oxide particles may additionally comprise one or more dispersing agents such as, for example, a sorbitan ester such as sorbitan isostearate, a polyoxyalkylenated fatty acid and glycerol ester such as TRLPPG3 MYRISTYLETHER CITRATE and POLYGLYCERYL-3 POLYRICINOLEATE. Preferably, the oily dispersion of titanium oxide particles comprises at least one dispersing agent chosen from polyoxyalkylenated fatty acid and glycerol esters.More particularly, mention may be made of 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 ISOSTERATE with the 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.

[0156] Uncoated titanium oxide pigments are, for example, sold by the company TAYCA under the trade names "MICROTITANIUM DIOXIDE MT 500 B” or "MICROTITANIUM DIOXIDE MT600 B®", by the company DEGUSSA under the name "P 25", by the company WACKHER under the name "Transparent titanium oxide PW®", by the company MIYOSHI KASEI under the name "UFTR®", by the company TOMEN under the name "ITS®" and by the company TIOXIDE under the name "TIOVEIL AQ".

[0157] Uncoated zinc oxide pigments are, 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.

[0158] Coated zinc oxide pigments are for example: - those marketed under the name “Oxide zinc 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®, benzoate of C12-C15 alcohols); - 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 with silica and polymethylhydrogensiloxane); - 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 with silicone-grafted acrylic polymer, dispersed in cyclodimethylsiloxane); - those marketed under the name "Escalol Z100®" by the company ISP (alumina-treated ZnO 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).

[0159] Uncoated cerium oxide pigments may be, for example, those sold under the name "COLLOÏDAL CERIUM OXIDE®" by the company RHONE POULENC.

[0160] 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®".

[0161] 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 "TRANSPARENT IRON OXIDE".

[0162] Mention may also be made of mixtures of metal oxides, in particular 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.

[0163] According to the invention, titanium oxide pigments, coated or uncoated, are particularly preferred.

[0164] The complementary UV filters according to the invention may 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

[0165] The composition in accordance with the present invention may further comprise conventional cosmetic adjuvants, in particular chosen from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, anti-foaming agents, perfumes, preservatives, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active ingredients, fillers, polymers, propellants, alkalizing or acidifying agents or any other ingredient usually used in the cosmetic and / or dermatological field.

[0166] Among the organic solvents, mention may be made of short-chain monoalcohols, for example C1-C4, such as ethanol and isopropanol, short-chain polyols 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.

[0167] According to a preferred embodiment, it is possible to use more particularly ethanol, propylene glycol, glycerin, and their mixtures.

[0168] As thickeners, mention may be made of carboxyvinyl polymers such as Carbopols® (Carbomers) and Pemulen such as Pemulen TRI® and Pemulen TR2® (acrylate / C10-C30-alkylacrylate copolymer); polyacrylamides such as, for example, 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; polymers and copolymers of 2-acrylamido 2-methylpropane sulfonic acid, optionally crosslinked and / or neutralized, such as poly(2-acrylamido 2-methylpropane sulfonic acid) marketed by the company Hoechst under the trade name “Hostacerin AMPS®” (CTFA name: ammonium polyacryloyldimethyl taurate or SIMULGEL 800® marketed by the company SEPPIC (CTFA name: sodium polyacryolyldimethyl taurate / polysorbate 80 / sorbitan oleate);copolymers of 2-acrylamido 2-methylpropane sulfonic acid and hydroxyethyl acrylate such as SIMULGEL NS® and SEPINOV EMT 10® marketed by the company SEPPIC; cellulose derivatives such as hydroxyethylcellulose; polysaccharides and in particular gums such as xanthan gum; water-soluble or water-dispersible silicone derivatives such as acrylic silicones, polyether silicones and cationic silicones and their mixtures.

[0169] Among the acidifying agents, mention may be made, for example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.

[0170] Among the alkalizing agents, mention may be made, by way of example, of ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides.

[0171] Preferably, the cosmetic composition comprises one or more alkalizing agents chosen from alkanolamines, in particular triethanolamine, and sodium hydroxide.

[0172] Among the active ingredients for the care of keratin materials such as the skin, lips, scalp, hair, eyelashes or nails, we can cite for example vitamins and their derivatives or precursors, alone or in mixtures; anti-oxidant agents; anti-free radical agents; anti-polluting agents; self-tanning agents; agents anti-glycation; soothing agents; deodorant agents; essential oils; NO-synthase inhibitors; agents stimulating the synthesis of dermal or epidermal macromolecules and / or preventing their degradation; agents stimulating the proliferation of fibroblasts; agents stimulating the proliferation of keratinocytes; muscle relaxants; refreshing agents; tightening agents; matting agents; depigmenting agents; pro-pigmenting agents; keratolytic agents; desquamating agents; moisturizing agents; anti-inflammatory agents; antimicrobial agents; slimming agents; agents acting on the energy metabolism of cells; insect repellents; substance P or CRGP antagonists; anti-hair loss agents; anti-wrinkle agents; anti-aging agents.

[0173] 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.

[0174] Of course, those skilled in the art will take care to choose the possible additional compound(s) mentioned above and / or their quantities in such a way that the advantageous properties intrinsically attached to the compositions in accordance with the invention are not, or not substantially, altered by the addition(s) envisaged. DOSAGE FORMS

[0175] The compositions in accordance with the invention may be aqueous or anhydrous.

[0176] When the compositions are aqueous, they contain at least one aqueous phase.

[0177] They can then be in purely aqueous form, that is to say they comprise a quantity of fatty phase of 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 in accordance with the invention is essentially aqueous, that is to say it is free of fatty phase.

[0178] The compositions according to the invention may also be presented in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / O or W / O / W) such as a cream, a milk or a cream gel.

[0179] In the case where the composition in accordance with the invention is aqueous, and it is possible to measure its pH, this is generally between approximately 3 and 12, preferably between approximately 5 and 9, and even more particularly from 5.5 to 8.

[0180] The compositions may also be in anhydrous form, such as for example in the form of an oil, an alcoholic solution or a glycolic solution. The term “anhydrous composition” means a composition containing less than 1% by weight of water, or even less than 0.5% of water, and in particular free of water, the water not being added during the preparation of the composition but corresponding to the water residual provided by the mixed ingredients. They can possibly be packaged in aerosol form and come in the form of foam or spray.

[0181] 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, rotor-stator and HHP type.

[0182] To obtain stable emulsions with a low polymer content (oil / polymer ratio >25), it is possible to make the dispersion in concentrated phase then dilute the dispersion with the rest of the aqueous phase.

[0183] It is also possible, by HHP (between 50 and 800 bars), to obtain stable dispersions with drop sizes that can go down to 100 nm.

[0184] The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or non-ionic emulsifiers, used alone or as a mixture. The emulsifiers are chosen appropriately depending on the emulsion to be obtained (W / O or O / W).

[0185] As examples of W / O emulsifying surfactants, mention may be made of alkyl esters or ethers of sorbitan, glycerol, polyol, glycerol or sugars; silicone surfactants such as dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name "DC 5225 C®" by the company Dow Corning, and alkyl-dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid" by the company Dow Corning; Cetyl dimethicone copolyol such as the product sold under the name Abil EM 90R® by the company Goldschmidt and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles) and hexyl laurate sold under the name ABIL WE 09® by the company Goldschmidt. One or more co-emulsifiers may also be added, which, advantageously, may be chosen from the group comprising polyol alkyl esters.

[0186] Mention may also be made of non-silicone emulsifying surfactants, in particular alkyl esters or ethers of sorbitan, glycerol, polyol or sugars.

[0187] As alkylated polyol esters, mention may in particular be made of polyethylene glycol esters such as PEG-30 Dipolyhydroxystearate such as the product marketed under the name Arlacel P135® by the company ICI.

[0188] As glycerol and / or sorbitan esters, mention may be made, for example, of polyglycerol isostearate, such as the product marketed under the name Isolan GI 34® by the company Goldschmidt; sorbitan isostearate, such as the product marketed under the name Arlacel 987® by the company ICI; sorbitan isostearate and glycerol, such as the product marketed under the name Arlacel 986® by the company ICI, and mixtures thereof.

[0189] For H / W emulsions, examples of emulsifying surfactants that may be mentioned are: non-ionic polyoxyalkylenated (more particularly polyoxyethylenated and / or polyoxypropylenated) fatty acid esters of glycerol; oxyalkylenated sorbitan fatty acid esters; polyoxyalkylenated (in particular polyoxyethylenated and / or polyoxypropylenated) fatty acid esters, possibly in combination with a fatty acid and glycerol ester such as the PEG-100 Stearate / Glyceryl Stearate mixture marketed for example by the company ICI under the name Arlacel 165; oxyalkylenated (oxyethylenated and / or oxypropylenated) fatty alcohol ethers; sugar esters such as sucrose stearate; fatty alcohol and sugar ethers, in particular alkylpolyglucosides (APG) such as decylglucoside and laurylglucoside marketed for example by Henkel under the respective names Plantaren 2000® and Plantaren 1200®, cetostearylglucoside possibly in a mixture with cetostearyl alcohol,marketed for example under the name Montanov 68® by the company Seppic, under the name Tegocare CG90® by the company Goldschmidt and under the name Emulgade KE3302® by the company Henkel, as well as arachidyl glucoside, for example in the form of the mixture of arachidic and behenic alcohols and arachidylglucoside marketed under the name Montanov 202® by the company Seppic. According to a particular embodiment of the invention, the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, as described for example in document WO-A-92 / 06778.

[0190] When it is an emulsion, the aqueous phase thereof may comprise a non-ionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins. J. Mol. Biol. 13, 238 (1965), FR 2 315 991 and FR 2 416 008).

[0191] The compositions according to the invention find their application in a large number of treatments, in particular cosmetic treatments, 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 making up the skin and / or lips.

[0192] Another object of the present invention consists of the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and / or scalp, in particular care products, sun protection products and makeup products.

[0193] The cosmetic compositions according to the invention can, for example, be used as a makeup product.

[0194] Another subject of the present invention consists of a non-therapeutic cosmetic process for caring for and / or making up a keratin material consisting of applying to the surface of said keratin material at least one composition according to the invention as defined above.

[0195] Another object of the invention consists of the use of dipropylene glycol to solubilize a merocyanine of formula (3) as defined above.

[0196] According to a particular embodiment, dipropylene glycol makes it possible to solubilize the merocyanines in accordance with the invention in the fatty phase and / or in the aqueous phase.

[0197] The cosmetic compositions according to the invention can, for example, be used as a care and / or sun protection product for the face and / or body of liquid to semi-liquid consistency, such as milks, more or less creamy creams, gel-creams, pastes. They can optionally be packaged as an aerosol and be in the form of a mousse or spray.

[0198] The compositions according to the invention in the form of vaporizable fluid lotions in accordance with the invention are applied to the skin or hair in the form of fine particles by means of pressurization devices. The devices in accordance with the invention are well known to those skilled in the art and include non-aerosol pumps or "atomizers", aerosol containers comprising a propellant as well as aerosol pumps using compressed air as a propellant. The latter are described in US patents 4,077,441 and US 4,850,517.

[0199] The compositions packaged in aerosol form in accordance with the invention generally contain conventional propellants such as, for example, the hydrofluorinated compounds dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane, trichlorofluoromethane. They are preferably present in amounts ranging from 15 to 50% by weight relative to the total weight of the composition. ASSEMBLY

[0200] According to another aspect, the invention also relates to a cosmetic assembly comprising: (i) a container delimiting one or more compartment(s), said container being closed by a closing element and possibly being non-watertight; and ii) a makeup and / or care composition in accordance with the invention placed inside said compartment(s).

[0201] The container may for example be in the form of a pot or a box.

[0202] The closing element may be in the form of a cover comprising a mounted hood movable by translation or by pivoting relative to the container housing said makeup and / or care composition(s). EXAMPLES

[0203] The following examples serve to illustrate the invention without, however, being limiting in nature.

[0204] Example A1: Preparation of compound (14) [formula 14]

[0205] 122.23 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-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.

[0206] The base / solvent combinations indicated in the following table are used. [Tables 2] Example Base Solvent Example ALI DBU (l,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-amylalcohol Example A 1.5 3-Methoxypropylamine toluene Example A 1.6 3-Methoxypropylamine dimethylformamide Example A 1.7 3-Methoxypropylamine solvent-free Example A 1.8 N-Morpholine isopropanol

[0207] The completion of the alkylation reaction can be monitored for example by methods such as TLC, GC or HPLC.

[0208] 162.30 grams of compound (14) are obtained in the form of a brown oil.

[0209] After crystallization, the product is obtained in the form of yellowish crystals.

[0210] Melting point: 92.7°C.

[0211] Example A2: Preparation of compound (15) [formula 15] H

[0212] 101.00 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-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.

[0213] The base / solvent combinations indicated in the following table are used. [Tables 3] Example Base Solvent Example A2.1 DBU (l,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-amylalcohol Example A2.5 3-methoxypropylamine toluene Example A2.6 3-methoxypropylamine dimethylformamide Example A2.7 3-methoxypropylamine solvent-free

[0214] The crude product (15) is obtained in the form of a dark brown oil.

[0215] After chromatography on a silica gel column (eluent: toluene / methanol 99 / 1), 81.8 grams of product are obtained in the form of yellowish crystals.

[0216] Melting point: 84.7-85.3 °C.

[0217] Example A3: Preparation of compound (27) [formula 27]

[0218] 13.09 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-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.

[0219] The base / solvent combinations indicated in the following table are used. [Tables 4] Example Base Solvent Example A3.1 DBU (l,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-amylalcohol Example A3.5 3-Methoxypropylamine toluene Example A3.6 3-Methoxypropylamine dimethylformamide Example A3.7 3-Methoxypropylamine solvent-free

[0220] 15.97 grams of crude product (27) are obtained in the form of a dark brown oil.

[0221] After chromatography on a silica gel column (eluent: toluene / acetone), 13.46 grams of product are obtained in the form of yellowish crystals.

[0222] Melting point: 96.3°C.

[0223] Example A4: Preparation of compound (25) [formula 25]

[0224] 148.4 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-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.

[0225] The base / solvent combinations indicated in the table below are used. [Tables 5] Example Base Solvent Example A4.1 DBU (l,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-amylalcohol Example A4.5 3-Methoxypropylamine toluene Example A4.6 3-Methoxypropylamine dimethylformamide Example A4.7 3-Methoxypropylamine solvent-free

[0226] Example of preparation of acrylic polymers:

[0227] Determination of molecular weight by gel permeation chromatography (GPC):

[0228] The sample is prepared by making a solution of the polymer at 10 mg / ml in tetrahydrofuran. The sample is placed in an oven at 54 °C for 10 minutes and then in an oscillating shaker for 60 minutes to aid dissolution. Upon visual inspection, the sample appears completely dissolved in the solvent.

[0229] 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 standards used for calibration were Agilent Technologies' Easi Vial narrow polystyrene (PS) standards.

[0230] Polystyrene standards ranging from 2,520,000 to 162 Daltons were used for calibration.

[0231] 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 by the Win GPC Unichrom 81 program.

[0232] Determination of melting point by differential scanning calorimetry (or DSC)

[0233] 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.

[0234] Behenyl acrylate / 2-hydroxyethyl acrylate copolymer (Polymer I):

[0235] In a 4-necked flask equipped with a side-blade stirrer, an internal thermometer, two funnels, a reflux condenser, and an extension for two more 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 for 60 minutes at 80 °C in 40 g of isopropanol with stirring after removing oxygen from the system using a nitrogen purge for 20 minutes. The mixture was stirred at 80 °C for 3 hours. Then the solvent was removed by vacuum distillation, and then 1 g of dilauryl peroxide and the reaction was continued for 60 minutes at 110 °C. The step was repeated. The mixture was then cooled to 90 °C and a jet of deionized water was added and stirred. The water was removed by vacuum distillation.

[0236] Molecular weight: Mn = 7300 g / mol, Mw = 21000, Mw / Mn = 2.8

[0237] Melting point: 65°C

[0238] Stearyl acrylate / 2-hydroxyethyl acrylate copolymer (Polymer 2):

[0239] In a 4-necked flask equipped with a side-blade stirrer, a thermometer Using an internal condenser, two funnels, a reflux condenser, and an extension for two more 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 for 90 minutes at 80 °C in 50 g of isopropanol with stirring after removing oxygen from the system using a nitrogen purge for 20 minutes. The mixture was stirred at 80 °C for 3 hours. Then the solvent was distilled off under vacuum, then 1 g of dilauryl peroxide was added, and the reaction was continued for 60 minutes at 125 °C. The step was repeated. The mixture was then cooled to 90 °C and a jet of deionized water was added, followed by stirring. The water was removed by vacuum distillation.

[0240] Molecular weight: Mn = 7500 g / mol, Mw = 19000, Mw / Mn = 2.6

[0241] Melting point: 49°C

[0242] Examples of formulations

[0243] In these examples, the quantities of the composition ingredients are given in % by weight of raw materials relative to the total weight of the composition.

[0244] Solubility assessment protocol

[0245] The solubility of merocyanine in aqueous and / or oily solutions can be assessed macroscopically and / or microscopically. Merocyanine is considered soluble if, at room temperature, the solution appears clear and translucent to the eye, and does not show visible crystals under a microscope in white or polarized light (x20 to x40 objective).

[0246] In the following examples, solubility is evaluated macroscopically. It is evaluated at room temperature, on the day the solution is prepared and then over time. During this time, the solutions are stored at room temperature.

[0247] Comparative examples 1 to 3

[0248] The following solutions were prepared according to the method below. [Tableauxô] Ingredients 1 (not included in the invention) 2 (not included in the invention) 3 (not included in the invention) Compound (25) 5 5 5 Glycerin 95 - - Propylene glycol - 95 - Dipropylene glycol - - 95 Solubility at t0 insoluble soluble soluble Solubility at 24 hours at room temperature - insoluble soluble Solubility at 1 month at room temperature insoluble soluble

[0249] Method of preparing compositions 1 to 3

[0250] The different raw materials are introduced successively into a container before being mixed using a magnetic stirrer and being heated to 80 to 90°C for 10 minutes to 1 hour, until all the compounds are dissolved.

[0251] The mixture is then left to stand to return to room temperature.

[0252] Results

[0253] The preceding tests show that dipropylene glycol significantly improves the solubility of merocyanines.

[0254] Comparative Examples 4 and 5 - Aqueous Serum

[0255] The following composition was prepared according to the method below. [Paintings?] Phase Ingredients Example 4 (outside invention) Example 5 (invention) Al PROPANEDIOL 3 3 Al Chelating agent 0.3 0.3 Al CAPRYLYL GLYCOL 0.3 0.3 Al PROPYLENE CARBONATE 20 20 Al DIPROPYLENE GLYCOL - 20 Al PEG-8 - Polyethylene glycol (8 EO) 20 - Al METHOXYPROPYLAMINO CYCLOHEXE-NYLIDENE ETHOXYETHYLCYA-NOACETATE (compound 25) 3 3 A2 AQUA 48.4 48.4 B ALCOHOL DENAT. 5 5

[0256] Preparation method:

[0257] Mix all the ingredients of phase A1 and slowly add the water from phase A2, heating to 50°C and stirring with a magnetic bar. Once the mixture is clear, let it return to room temperature and add the ethanol.

[0258] The mixture is stored at room temperature for 2 months.

[0259] The state of solubility is determined macroscopically by the naked eye and verified under an optical microscope.

[0260] Results:

[0261] After two months at room temperature, crystallization of compound 25 is observed in composition 4, which is not the case in composition 5.

[0262] These comparative examples show that the presence of dipropylene glycol in the composition makes it possible to improve the solubility of compound 25.

[0263] Example 6 - Aqueous serum

[0264] The following composition was prepared according to the method below. [Tables 8] Phase Ingredients Example 6 (invention) Al CAPRYLYL GLYCOL - Octane- 1,2-diol 0.3 Al PROPANEDIOL - Propane-1,3-diol 3 Al POLYSORBATE 20 - Oxyethylenated sorbitan monolaurate (20 EO) 1 Al PEG-8 - Polyethylene glycol (8 EO) 10 Al DIPROPYLENE GLYCOL 10 Al METHOXYPROPYLAMINO CYCLOHEXE-NYLIDENE ETHOXYETHYLCYANOACETATE (compound 25) 3 A2 AQUA 37 A2 TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID (Mexoryl SX from Noveal) 12 A2 PHENYLBENZIMIDAZOLE SULFONIC ACID (Eusolex 232 from Merck) 8 A2 pH adjuster qs pH 6.8 B ALCOHOL DENAT. 10

[0265] Preparation method:

[0266] Mix all the ingredients of phase Al by heating to 50°C and stirring magnetically until a clear mixture is obtained. Prepare phase A2 by heating to 50°C and stirring until a clear mixture is obtained. Slowly add phase A2 to phase Al. Once the mixture is clear, let it return to room temperature and introduce the ethanol.

[0267] Example 7 - Cream [Tableaux9] Phase Ingrédients Exemple 7 Al AQUA 41,6 Al METHOXYPROPYLAMINO CYCLOHEXE-NYLIDENE ETHOXYETHYLCYANOACETATE (composé 25) 1,5 Al PEG-8 - Polyéthylène glycol (8 OE) 4 Al DIPROPYLENE GLYCOL 4 Al Conservateur(s) 0,5 Al Chelatant 0,3 A2 ACRYLATES COPOLYMER (Carbopol Aqua SF-1 de Lubrizol) 2 A3 TRIETHANOL AMINE 0,3 B1 BUTYL METHOXYDIBENZOYLMETHANE (Parsol 1789 de DSM Nutritional Products) 2 B1 ETHYLHEXYL SALICYLATE (Parsol EHS de DSM Nutritional Products) 5 B1 ETHYLHEXYL TRIAZONE (Uvinul T150 de BASF) 4,5 B1 DROMETRIZOLE TRISILOXANE (Mexoryl XL de Noveal) 2,5 B1 DIETHYLAMINO HYDROXYBENZOYL HEXYL HEXYL BENZOATE (Uvinul A Plus Granular de BASF) 1 B1 BIS-ETHYLHEXYLOXYPHENOL ME- THOXYPHENYL TRIAZINE (Tinosorb S de BASF) 3 B1 CAPRYLYL GLYCOL - Octane- 1,2-diol 0,3 B1 DIISOPROPYL SEBACATE 8 B1 DIISOPROPYL ADIPATE 4 B1 C12-22 ALKYL ACRYLATE / HY- DROXYETHYLACRYLATE COPOLYMER (Polymère 1) 2,5 B2 TITANIUM DIOXYDE (MT100 TV de Tayca) 2,5 Cl ACRYLATES / C10-30 ALKYL ACRYLATE 0,15 CROSSPOLYMER (Pemulen TR-1 Polymer from Lubrizol) Cl SODIUM POLYACRYLATE (Cosmedia SP from BASF) 0.2 C2 TRIETHANOL AMINE 0.15 D SILICA 1 D ALUMINUM STARCH OCTENYLSUCCINATE 2 E ALCOHOL DENAT. 7

[0268] Preparation method:

[0269] Phase A1 is prepared by mixing all the ingredients until a clear phase is obtained. Phase A2 is dispersed and then phase A3 is added to neutralize the gel and allow it to unfold. All of this preparation of the phase, which will subsequently be called A, is carried out by heating to 65°C and stirring with paddles (50 rpm).

[0270] Phase B1 is prepared by mixing all the ingredients while heating at 80°C with magnetic stirring until a clear and homogeneous phase is obtained. Phase B2 is then dispersed in Bl. This phase will be called phase B.

[0271] The emulsification is carried out by dispersing phase B in phase A at 65°C and with 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 reduced to return to room temperature while maintaining the same stirring until the end. Around 55°C, the thickeners of phase C1 are added (5 minutes), then neutralized with C2 to deploy the gels (5 minutes). The fillers of phase D are dispersed (5 minutes) from 35°C. Finally, the alcohol of phase E is added once the mixture has returned to room temperature.

[0272] Example 8

[0273] The following composition is prepared according to the method detailed below. [Tables 10] Phase Ingredients 8 (invention) Al Compound (25) 3% Al Propylene carbonate (Merck) 5% A2 Glycerin 6% A2 Dipropylene glycol (CABB Group GmbH) 5% A3 Terephthalylidene dicamphor sulfonic acid (Mexoryl SX from Noveal) 0.9% A3 Triethanolamine 0.15% A3 Nicotinamide (ThermoFisher) 2.5% A3 Sodium salicylate (Sigma Aldrich) 0.5% A3 Water QSP 70 A4 Ethanol (Sigma Aldrich) 4% Solubility at t0 soluble Solubility at 4°C after 4 weeks soluble

[0274]

[0275] Procedure:

[0276] Compound 25 is solubilized in propylene carbonate at 65°C with magnetic stirring (phase A1). Then, glycerin and dipropylene glycol are added (phase A2), then the solution containing phase A3 is introduced. Phase A3 has previously been prepared by mixing all the ingredients until solubilization. Finally, ethanol is added with gentle stirring after returning to room temperature.

[0277] Samples are kept at 4°C for 4 weeks. Solubility is assessed at the macroscopic scale by eye and at the microscopic scale under an optical microscope.

[0278] Example 9

[0279] The following composition is prepared according to the method as detailed below. Phase Ingrédients Concentration (%) Al EAU 20 Al TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID (Mexoryl SX de Noveal) 0,9 Al TRIETHANOLAMINE 0,35 Al NICOTINAMIDE (ThermoFisher) 2,5 Al SODIUM SALYCILATE (Sigma Aldrich) 0,5 A2 XANTHAN GUM 0,1 A2 GLYCERINE 6 A2 DIPORYLENE GLYCOL (CABB Group GmbH) 5 A2 ACRYLATES / C10-30 ALKYL ACRYLATE CROSSPOLYMER (Pemulen TR-1 polymer de Lubrizol) 0,25 A2 EAU 22 B1 STEARIC ACID 1,5 B1 GLYCERYL STEARATE (and) PEG-100 STEARATE (Arlacel 165-FP-PA-(SG) de Croda) 1,3 B1 HOMOSALATE 6 B1 BUTYL METHOXYDIBENZOYLMETHANE (Parsol 1789 de Dsm Nutritional Products) 4 B1 ETHYLHEXYL TRIAZONE (Uvinul T150 de BASF) 1,8 B1 ETHYLHEXYL SALICYLATE (Parsol EHS de DSM Nutriotional Products) 5 B1 ISOPROPYL PALMITATE (BASF) 7 B1 DIISOPROPYL SEBACATE (Dub Dis de Stearinerie Dubois) 1 B1 CAPRYLYL GLYCOL 0,4 B2 POTASSIUM CETYL PHOSPHATE (Amphisol K de DSM Nutrional Products) 1 B2 pH adjuster QS pH 6.3 Cl PROPYLENE CARBONATE (Merck) 6 Cl METHOXYPROPYLAMINO CYCLOHEXE-NYLIDENE ETHOXYETHYLCYANOACETATE (compound 25) 3 C2 ETHANOL (Sigma Aldrich) 4

[0280] Procedure:

[0281] Phases A1, B1 and C are prepared separately by mixing the ingredients that make up each phase, heating to 65°C with magnetic stirring, until a clear mixture is obtained.

[0282] The ingredients of phase B2 are introduced with stirring into phase B1 until a fine dispersion of potassium cetyl phosphate is obtained.

[0283] Phase A2 is prepared by dispersing the gelling agents in the glycols, before adding the water and mixing with an Ultraturrax at 27000 rpm for 5 minutes.

[0284] Phase C is prepared by introducing compound 25 into propylene carbonate with mechanical stirring and heating to 65°C until a clear mixture is obtained. Ethanol is then incorporated once the mixture has returned to room temperature.

[0285] Phases A1 and A2 are introduced into phase B1+B2 by mixing with Ultraturrax at 27000 rpm for 5 min to obtain an emulsion. Phase C is then incorporated by mixing with Ultraturrax at 27000 rpm for 5 minutes.

Claims

1. Claims 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]

2. 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) dipropylene glycol. 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 o, ,z- H 'T Æ. U % ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - y lidene} ethanoate 15 H „O -O. - u (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methox ypropyl)amino] cyclohex-2-en-1 -ylidene} ethanamide 25 / s ) Z Q X W Q V;--- \ ( ) \ 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - y lidene} ethanoate 27 (L O.-.s / 0. Jx j H ï r 1 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - y lidene} ethanoate 29 1 H 1 o < x -A. - 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - y lidene} ethanoate 31 0^ 0^0 x Z\ / O x, 1 H T f J 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - y lidene} ethanoate 37 ox CK ..CC 1 H 1 ' " 1 K JX 1 ~ {(J X 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - y lidene} ethanoate

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}ethanoate (25) in its geometric E / Z configuration of the following structure: [formula 3] 'N and / or in its geometric configuration E / E of the following structure: [formula 3bis] H N.

4.

5.

6. Composition according to any one of claims 1 to 3 in which the merocyanines of formula (3) and / or their isomeric geometric forms are present 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. Composition according to any one of claims 1 to 4, dipropylene glycol is present in an amount of between 0.1 and 99%, in particular between 0.5 and 50%, preferably between 1 and 25%, and even more preferably between 1 and 10%, for example between 1 and 5% by weight of the total weight of the composition. Composition according to any one of claims 1 to 5 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 the stearyl and behenyl radicals, the weight percentage relating 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 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.

7. Composition according to claim 6 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.

8. Composition according to any one of claims 6 and 7 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.

9. Composition according to any one of claims 6 to 8 in which in the additional polymer all the RI groups are stearyl or behenyl radicals.

10. Composition according to any one of claims 6 to 9 in which in the additional polymer said weight ratio ranges from 1:15 to 1:1, preferably ranges from 1:10 to 1:

4.

11. Composition according to any one of claims 6 to 10 in which the additional polymer has a number average molecular weight Mn ranging from 5,000 to 9,000 g / mol.

12. Composition according to any one of claims 6 to 11 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.

13. Composition according to any one of claims 6 to 12 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.

14. Composition according to any one of claims 6 to 13 in which in the additional polymer at least 60% by weight of the RI groups are behenyl radicals, and said additional polymer has

15.

16. a melting point ranging from 60°C to 70°C, and preferably ranging from 63°C to 67°C. Composition according to any one of claims 1 to 14 comprising at least one alkyl or alkylene carbonate. Composition according to claim 14 in which the alkylene carbonate(s) are chosen from those of the following formula: [formula 6]

17.

18.

19.

20.

21.

22. in which: R' denotes a hydrogen atom, a linear or branched C1-C6 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; R' ' represents a hydrogen atom, a linear or branched C1-C6 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; m is 1, 2 or 3, preferably 1. Composition according to claim 16 in which the radical R' represents a hydrogen atom, a linear or branched CrC4 alkyl radical, a linear or branched Ci-C2 hydroxyalkyl radical. Composition according to any one of claims 16 and 17 in which R” represents a hydrogen atom, a linear or branched C1-C2 alkyl radical, a linear or branched C1-C2 hydroxyalkyl radical. Composition according to any one of claims 15 to 18 in which the alkylene carbonate used is propylene carbonate. Composition according to any one of claims 1 to 19 further comprising one or more additional UV filters. Non-therapeutic cosmetic process for caring for and / or making up a keratin material comprising the application to the surface of said keratin material of at least one composition as defined in any one of claims 1 to 20. Use of dipropylene glycol for solubilizing a merocyanine as defined in any one of claims 1 to 3, in particular in fatty phase and / or aqueous phase.