FR2888113A1 - Cosmetic composition to manufacture care, make-up and cosmetic products for skin, lips, nails, hair, lashes, eyebrows and/or scalp, comprises a benzylidene compound in a medium - Google Patents

Abstract

Composition comprises a benzylidene compound (I) in a medium. Composition comprises an aromatic amine compound of formula (I) in a medium. X = C(O)R3, SO2R3 or C(O)OR3; Y1 = O or NR4; R4 = H or 1-5C alkyl; and R1-R3 = 1-30C alkyl or 3-30C alkenyl (both optionally substituted by one or more OH and/or interrupted by a cyclic alkyl and/or one or more O, N or Si) or optionally substituted 6-20C aryl. Independent claims are included for: (1) new compounds (I), excluding the specific compound 4'-acetylaminobenzalmalonate diethyl ester; and (2) a process for preparation of (I) comprising either: (a) condensing para-aminobenzaldehyde with an acid chloride, anhydride, sulfochloride or a chloroformate of formula XCl to obtain a benzaldehyde compound of formula (II) and subjecting (II) to Knoevenagel reaction followed by reacting with a malonate compound of formula (III); or (b) condensing an amino compound of formula (IV) with the chloroformate compound. [Image] [Image].

Description

X

NH

Y (1)

  A photoprotective composition containing an amide, sulfonamide or carbamate derivative of a benzalmalonic acid ester; new compounds; preparation methods; uses.

  The invention relates to compositions comprising, in a cosmetically acceptable medium, at least one amide, sulfonamide or carbamate derivative of a benzalmalonic acid ester of formula (1) which will be defined in more detail below.

  The invention also relates to novel amide, sulphonamide or carbamate derivatives of an ester of benzalmalonic acid of formula (1) and their uses as UV filters and in particular as UV-B filters.

  It is known that wavelength radiations of between 280 nm and 400 nm allow the browning of the human epidermis, and that the radiations of wavelengths between 280 and 320 nm known under the name of UV-B radiation. , cause erythema and skin burns that can affect the development of natural tanning. For these reasons as well as for aesthetic reasons, there is a growing demand for means of control of this natural tan. It is therefore necessary to filter this UV-B radiation.

  It is also known that UV-A rays of wavelengths between 320 and 400 nm, causing browning of the skin, are capable of inducing an alteration thereof, particularly in the case of sensitive skin. and / or continuously exposed to solar radiation. UV-A rays cause in particular a loss of elasticity of the skin and the appearance of wrinkles leading to premature cutaneous aging. They promote the triggering of the erythematous reaction or amplify this reaction in some subjects and may even be the cause of phototoxic or photoallergic reactions. Thus, for aesthetic and cosmetic reasons such as the preservation of the natural elasticity of the skin, more and more people want to control the effect of UV-A on their skin. Sun protection factor means the ratio of the irradiation time required to reach the erythematogenic threshold in the presence of the filter tested at the irradiation time required to reach the same threshold in the absence of filter.

  The organic filters are most often formulated in compositions present in the form of oil-in-water or water-in-oil emulsions. The organic filters, generally lipophilic or hydrophilic, are present in dissolved form, in one or the other other of these phases, in appropriate amounts to obtain the desired sun protection factor (SPF).

  Sun protection factor means the ratio of the irradiation time required to reach the erythematogenic threshold in the presence of the filter tested at the irradiation time required to reach the same threshold in the absence of filter.

  In addition to their filtering ability of the solar radiation, the photoprotective compounds must also have good cosmetic properties, good solubility in the usual solvents and in particular in aqueous media and a satisfactory photostability.

  The Applicant has surprisingly discovered a new family of amine derivatives, amides, sulfonamides or carbamates esters of benzalmalonic acid having absorption properties in the UV-B radiation zone (UV-A as for the amine derivatives). These compounds can be incorporated into cosmetic formulations. They have good solubility in cosmetic oils, good photostability and have satisfactory cosmetic qualities.

  The invention also relates to a composition, intended for the photoprotection of keratinous substances, containing in a cosmetically acceptable medium at least one compound of formula (1). By cosmetically acceptable, is meant compatible with the skin and / or its integuments, which presents a color, a pleasant smell and touch and that does not generate unacceptable discomfort (tingling, tightness, redness), likely to divert the consumer to use this composition.

  The invention also relates to the use of a compound of formula (1) in a cosmetic composition as a filtering agent for UV radiation and in particular for wavelengths between 280 and 320 nm (UV-B).

  Other objects will appear in the light of the description.

  The compounds according to the present invention correspond to the general formula (1): X

NH

  (1) R "Y in which: X represents a radical R3- (C = O) -, R3-SO2- or R3-O (C = O) -, Y represents -O- or NR4, with R4 representing hydrogen or a linear or branched C1-C5 alkyl radical, R1, R2 and R3, which may be identical or different, represent a linear or branched C3-C30 alkyl or C3-C30 alkenyl radical which may carry one or more hydroxyl substituents and may contain in the carbon chain an alkyl ring, one or more heteroatoms selected from oxygen, nitrogen and silicon atoms, an optionally substituted C 6 -C 20 aryl radical.

  In the formula (1) above, the alkyl radicals may be chosen in particular from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl and n-hexyl radicals. , n-heptyl, n-octyl, 2-ethylhexyl, tert-octyl, cyclohexyl, menthyl, 2-butyl octyl, 2-hexyl decyl, 2-ethyldodecyl, 2-decyltetradecyl, 2-dodecyl cetyl or 2-isohexyl isooctyl.

  Among the compounds of formula (1), use will be made preferably of those in which the radicals R 1, R 2 and R 3 denote a C 1 -C 22 alkyl with the sum of the carbons present for the 3 radicals R 1, R 2 and R 3 being a greater number or equal to 9.

  Among these compounds, those for which X is R 3 - (C = O) - are more particularly preferred.

  Among these compounds, those selected from the following derivatives of formulas (a) to (i) will be chosen even more particularly:

O

  H3C (CH2) 15 / NH (f) / OO (g) H3C- (CH2)

NH (i)

H3C- (CH2) 12

NH

  The compounds of formula (1) of the invention are new except for the compound of formula: (Y = O, R1 = R2 = -CH2CH3, X = - (C = O) -CH3); they constitute as such another object of the invention. // NH

  The compounds of formula (1) according to the invention can be obtained by the following two synthesis routes: Route A: a) By condensation of the para-aminobenzaldehyde of formula (2) with an acid chloride, an anhydride, a sulfochloride or chloroformate of formula (3) in which X is a radical R3- (C = O) -, R3-SO2- or R3-O- (C = O) - in which R3 has the same meaning indicated in formula (1) ) defined above, to obtain the corresponding benzaldehyde compound of formula (4) followed b) a Knoevenagel reaction between the benzaldehyde of formula (4) thus obtained and a malonate compound of formula (5) in which Y, R, and R2 have the same meanings indicated in formula (1) defined above according to the following reaction scheme:

X

NH 'NH

O O

+ X-CI + HCI (4)

O Y, R1

  OY, R2 (1) (5) Route B: By condensation of an amino compound of formula (6) in which Y, R, and R2 have the same meanings indicated in formula (1) defined above on a compound of formula (3) as defined above according to the following reaction scheme: Y-R 1 Y-R 2 (6) (3) The amine derivatives of formula (6), starting products of synthesis B can be obtained by the two synthetic routes following: Channel C: a) By Knoevenagel reaction between the para-nitro benzaldehyde of formula (7) and the malonic compound of formula (5) in which Y, R, and R2 have the same meanings indicated in formula (1) defined above in a solvent such as toluene and in the presence of a catalyst such as piperidinium acetate followed b) a reduction reaction of the nitro derivative of formula (8) obtained with an iron catalyst, nickel or platinum for example in the presence of nascent hydrogen or under hydrogen pressure according to the following reaction scheme to give the aminobenzalmalonate of formula (6) accompanied, whatever the reduction route, by a significant amount of the corresponding hydrogenated derivative of formula (9) in which R 1 and R 2 have the same meanings indicated in the formula (1) defined above: Catalyst Reduction Route D: a) By Knoevenagel reaction between para-acetamido benzaldehyde of formula (10) and the malonic compound of formula (5) in which Y, R, and R2 have the same meanings indicated in the formula (1) defined above in a solvent such as toluene and in the presence of a catalyst such as piperidinium acetate followed b) a simple hydrolysis in the presence of dilute HCl for example and in the presence of a solvent such as isopropanol or dioxane, for example at a temperature of between 20 and 80 ° C., according to the following reaction scheme: ## STR2 ## R (7) (5) z (8) O 2 Y RI RfY (8) ( 6) R (Y (9) Y R 2 / H 2 N + AcOH Hydrolysis The advantages of this route D with respect to the C route are the following: - first step: the kinetics of the reaction of the D route is significantly improved with regard to the C route and the recrystallization purification of the products, from a yield of about 80% for the C route to a yield of about 95% for the D route. catalytic pathway C involves expensive catalysts and non-selective resulting in a quantity of impurity reduced product of formula (9) of the order of more than 10% does not facilitate the purification methods by recrystallization and not giving average yields of own product less than 80%.

  the hydrolysis of the D route can be carried out in a gentle manner (without trans esterifying the esters present) with yields greater than 90%.

  Among the compounds of formula (6), mention will be made more particularly of those of the following formulas (j) to (n): H 2 N (i) H 2 N (n) The compounds of formula (1) are generally present in the composition of the invention in proportions of between 0.01% and 20% by weight, preferably between 0.1% and 10% by weight, relative to the total weight of the composition.

  The compositions in accordance with the invention may comprise, in addition, other additional organic UV or inorganic UV screening agents active in water-soluble or fat-soluble UVA and / or UVB or insoluble in the cosmetic solvents commonly used.

  The complementary organic screening agents are chosen in particular from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives such as those described in patent applications US 4,367,390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469, EP933376, EP507691, EP507692, EP790243, EP944624; benzophenone derivatives; X3,13-diphenylacrylate derivatives; benzotriazole derivatives; benzalmalonate derivatives other than those of formula (1); benzimidazole derivatives; imidazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US 2,463,264; paminobenzoic acid derivatives (PABA); methylene bis- (hydroxyphenylbenzotriazole) derivatives as described in US 5,237,071, US 5,166, 355, GB2303549, DE19726184 and EP893119; filter polymers and silicone filters such as those described in particular in application WO-93/04665; alkyl-styrene-derived dimers such as those described in patent application DE19855649; 4,4-diarylbutadienes as described in Applications EP0967200, DE19746654, DE19755649, EP-A-1008586, EP1133980 and EP133981 and mixtures thereof.

  As examples of complementary organic filters, mention may be made of those referred to below under their INCI name: Derivatives of para-aminobenzoic acid: 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 P25 by BAS F, Salicylic derivatives: Homosalate sold under the name Eusolex HMS by Rona / EM Industries, Ethylhexyl salicylate sold under the name NEO HELIOPAN OS by HAARMANN and REIMER, Dipropylene glycol salicylate sold under the name DIPSAL by SCHER, TEA Salicylate, sold under the name NEO HELIOPAN TS by HAARMANN and REIMER, Derivatives of dibenzoylmethane: Butyl Methoxydibenzoylmethane sold in particular under the trade name 20 PARSOL 1789 by ROCHE VITAMINS, Isopropyl Dibenzoylmethane, cinnamic derivatives: Ethylhexyl Methoxycinnamate sold in particular under the trade name PARSOL 25 MCX by ROCHE VITAMINS, Isopropyl Methoxy cinnamate, Isoamyl Methoxy Cinnamate sold under the trade name NEO HELIOPAN E 1000 by HAARMANN and REIMER, Cinoxate, DEA Methoxycinnamate, Diisopropyl Methylcinnamate, Glyceryl Ethylhexanoate Dimethoxycinnamate Derivatives of [3, [3'-d] -phenylacrylate: Octocrylene sold in particular under the trade name UVINUL N539 by BASF, Etocrylene, sold in particular under the trade name UVINUL N35 by BASF, Derivatives of benzophenone: Benzophenone-1 sold under the trade name UVINUL 400 by BASF, Benzophenone-2 sold under the trade name UVINUL D50 by BASF Benzophenone-3 or Oxybenzone, sold under the trade name UVINUL M40 by BASF, Benzophenone-4 sold under the trade name UVINUL MS40 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-diethylamines) n-hexyl 2-hydroxybenzoyl) benzoate.

  Derivatives of benzylidene camphor: 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 name 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, Derivatives of phenyl benzimidazole: Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name Eusolex 232 by Merck, Disodium Phenyl Dibenzimidazole Tetrasulfonate sold under the trade name NEO HELIOPAN AP by HAARMANN and REIMER, Triazine derivatives: Triazine derivatives: Bis- Ethylhexyloxyphenol Methoxyphenyl Triazine sold under the trade name TINOSORB S by CIBA GEIGY, Ethylhexyl triazone sold in particular under the name of Commercial UVINUL T150 by BASF, Diethylhexyl Butamido Triazone sold under the trade name UVASORB HEB by SIGMA 3V, 2,4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine, 2,4,6-tris ( Dineopentyl 4'-amino benzalmalonate) -s-triazine Derivatives of phenyl benzotriazole: Drometrizole Trisiloxane sold under the name Silatrizole by Rhodia Chimie Methylene bis-Benzotriazolyl Tetramethylbutylphenol, sold in solid form under the trade name MIXXIM BB / 100 by FAIRMOUNT CHEMICAL or under micronized form in aqueous dispersion under the trade name TINOSORB M by CIBA SPECIALTY CHEMICALS, Anthranilic derivatives: Menthyl anthranilate sold under the trade name NEO HELIOPAN MA by HAARMANN and REIMER, Imidazoline derivatives: Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate, Derivatives of benzalmalonate: Di -neopentyl 4'methoxybenzalmalonate Benzalmalonate-functional polyorganosiloxanes such as Polysilicone-15 sold under 45 la Trade name PARSOL SLX by ROCHE VITAMINS Derivatives of 4,4-diarylbutadiene: -1,1-dicarboxy (2,2'-dimethylpropyl) -4,4-diphenylbutadiene Derivatives of benzoxazole: 2,4-bis [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine sold under the name UVASORB K2A by SIGMA 3V.

and their mixtures.

  Preferred complementary organic UV filters are chosen from among Homosalate Ethylhexyl Salicylate, Ethylhexyl Methoxycinnamate Butyl Methoxydibenzoylmethane Octocrylene, Phenylbenzimidazole Sulfonic Acid, Benzophenone-3, Benzophenone-4, Benzophenone-5, 2- (4-diethylamino-2hydroxybenzoyl) benzoate n-hexyl .

  4-Methylbenzylidene camphor, Camphor Benzalkonium Methosulphate Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, 2,4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine Ethylhexyl triazone, Diethylhexylbutamido triazone, 2,4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine, 2,4,6-tris (4'-amino benzalmalonate dineopentyl) -s-triazine Methylene bis-Benzotriazolyl Tetramethylbutylphenol Drometrizole Trisiloxane Di-neopentyl 4'methoxybenzalmalonate Polysilicone-1,1-dicarboxy (2,2'-dimethyl-propyl) -4,4-diphenylbutadiene 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2- yl- (4phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine and mixtures thereof.

  The inorganic filters are chosen from pigments or even nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of coated or uncoated metal oxides, such as, for example, nanopigments. titanium oxide (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se.

  The pigments can be coated or uncoated.

  The coated pigments are pigments which have undergone one or more surface treatments of a chemical, electronic, mechanochemical and / or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, p. 53-64, 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.

  In a known manner, the silicones are organosilicon polymers or oligomers with a linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and / or polycondensation of suitably functionalized silanes, and essentially constituted by a repetition of patterns. in which the silicon atoms are connected to each other by oxygen atoms (siloxane bond), optionally substituted hydrocarbon radicals being directly bonded via a carbon atom to said silicon atoms.

  The term "silicones" also includes the silanes necessary for their preparation, in particular alkyl silanes.

  The silicones used for coating the nanopigments that are suitable for the present invention are preferably chosen from the group containing the alkyl silanes, the polydialkylsiloxanes, and the polyalkylhydrogensiloxanes. Even more preferentially, the silicones are chosen from the group containing octyl trimethyl silane, polydimethylsiloxanes and polymethylhydro-genosiloxanes.

  Of course, the metal oxide pigments before their treatment with silicones, may have been treated with other surfactants, in particular with cerium oxide, alumina, silica, aluminum, silicon compounds, or mixtures thereof.

  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, and Mirasun TiW 60 from the Rhodia company, - alumina such as the products "TIPAQUE TTO-55 (B)" and "TIPAQUE TTO-55 (A)" from ISHIHARA, and "UVT 14/4" from KEMIRA, - alumina and aluminum stearate such as the product "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 MERCK, - silica, alumina and alginic acid such as the product" MT-100 AQ "from TAYCA, - alumina and alumina laurate nium such as the product "MICROTITANIUM DIOXIDE MT 100 S" from 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 "BR351" from the company TAYCA, silica and alumina and treated with a silicone such as the products "MICROTITANIUM 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 KEMIRA, - alumina and treated with a silicone such as the products "TIPAQUE TTO-55 (S)" ISHIHARA, or "UV TITAN M 262 "from the company KEMIRA, triethanolamine such as the product" STT-65-S "from the company TITAN KOGYO, - stearic acid such as e product "TIPAQUE TTO-55 (C)" of the company ISHIHARA, - sodium hexametaphosphate such as the product "MICROTITANIUM DIOXIDE MT 150 W" from the company TAYCA.

  Other titanium oxide pigments treated with a silicone are preferably TiO 2 treated with octyl trimethyl silane and whose average elementary particle size is between 25 and 40 nm, such as that sold under the trade name "T 805 "by the company Degussa Silices, the TiO 2 treated with a polydimethylsiloxane and whose average elementary particle size is 21 nm, such as that sold under the trade name" 70250 Cardre UF TiO2S13 "by CARDRE, TiO2 anatase / rutile treated with a polydimethylhydrogensiloxane and whose average elementary particle size is 25 nm, such as that sold under the trade name "MICRO TITANIUM DIOXIDE USP GRADE HYDROPHOBIC" by the company COLOR TECHNIQUES.

  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 WACKHER company under the name "transparent titanium oxide PW", by MIYOSHI KASEI under the name "UFTR", by TOMEN under the name "ITS" and by the company TIOXIDE under the name "TIOVEIL AQ".

  The 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 Elementis; those marketed under the name "Nanogard WCD 2025" by Nanophase Technologies; The coated zinc oxide pigments are, for example, those sold under the name "Zinc Oxide CS-5" by the company Toshibi (ZnO coated with polymethylhydrogenosiloxane); those sold under the name "Nanogard Zinc Oxide FN" by Nanophase Technologies (as a 40% dispersion in Finsolv TN, C12-C15 alcohols benzoate); those marketed under the name "DAITOPERSION ZN-30" and "DAITOPERSION Zn-50" by Daito (dispersions in cyclopolymethylsiloxane / polydimethylsiloxane oxyethylenated, containing 30% or 50% of zinc nano-oxides coated with silica and polymethylhydrogeniloxane; ); those marketed under the name "NFD Ultrafine ZnO" by the company Daikin (ZnO coated with perfluoroalkyl phosphate and a copolymer based on perfluoroalkylethyl dispersed in cyclopentasiloxane); those marketed under the name "SPD-Z1" by Shin-Etsu (ZnO coated with silicone-grafted acrylic polymer, dispersed in cyclodimethylsiloxane); those marketed under the name "Escalol Z100" by the company ISP (ZnO treated alumina and dispersed in the mixture methoxycinnamate ethylhexyl / copolymer PVP-hexadecene / 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 Elementis (ZnO dispersed at 55% in C12-C15 alcohols benzoate with hydroxystearic acid polycondensate).

  Uncoated cerium oxide pigments are sold for example under the name "COLLOIDAL CERIUM OXIDE" by the company RHONE POULENC.

  Uncoated iron oxide nanopigments are for example sold by 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 ".

  The coated iron oxide pigments are for example sold by ARNAUD under the names "NANOGARD WCD 2008" (FE 45B FN) "," NANOGARD WCD 2009 (FE 45B 556) "," NANOGARD FE 45 BL 345 "," NANOGARD FE 45 BL ", or by the company BASF under the name" OXIDE OF CLEAR IRON ".

  Mention may also be made of mixtures of metal oxides, in particular titanium dioxide and cerium dioxide, including the titanium dioxide / silica-coated cerium-aluminum alloy mixture 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 KEMIRA or coated with alumina, silica and glycerine such that the product "M 211" sold by KEMIRA.

  The complementary UV filters according to the invention are generally present in the compositions according to the invention in proportions ranging from 0.01% to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.1% to 10% by weight relative to the total weight of the composition.

  The compositions according to the invention may also contain agents for artificial tanning and / or browning of the skin (self-tanning agents), and more particularly dihydroxyacetone (DHA). They are preferably present in amounts ranging from 0.1 to 10% by weight relative to the total weight of the composition.

  The aqueous compositions in accordance with the present invention may furthermore comprise conventional cosmetic adjuvants, chosen especially from fatty substances, organic solvents, ionic or nonionic thickeners, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, defoamers, perfumes, preservatives, anionic, cationic, nonionic, 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.

  The fatty substances may consist of an oil or a wax other than the apolar waxes as defined above or mixtures thereof. By oil is meant a liquid compound at room temperature. By wax is meant a compound which is solid or substantially solid at ambient temperature and whose melting point is generally greater than 35 C.

  As oils, mention may be made of mineral oils (paraffin); vegetable (sweet almond oil, macadamia oil, blackcurrant seed oil, jojoba oil); synthetics such as perhydrosqualene, alcohols, fatty amides (such as isopropyl lauroyl sarcosinate sold under the name of Eldew SL-205 by Ajinomoto), fatty acids or esters (such as benzoate of C 12 alcohols). C15 sold under the trade name Finsolv TN or Witconol TN by WITCO, octyl palmitate, isopropyl lanolate, triglycerides including those of capric / caprylic acids, dicaprylyl carbonate sold under the name Cetiol CC by the company Cognis), oxyethylenated or oxypropylene fatty esters and ethers, silicone (cyclomethicone, polydimethylsiloxane or PDMS) or fluorinated oils, polyalkylenes.

  Waxy compounds that may be mentioned include carnauba wax, beeswax and hydrogenated castor oil.

  Among the organic solvents, mention may be made of lower alcohols and polyols. These can be selected from glycols and glycol ethers such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.

  As hydrophilic thickeners, mention may be made of carboxyvinyl polymers such as Carbopols (Carbomers) and Pemulen (acrylate / C10-C30-alkylacrylate copolymer); polyacrylamides, for example crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide / C13-14 isoparaffin / Laureth 7) or Simulgel 600 (CTFA name: acrylamide / sodium acryloyldimethyltaurate copolymer / isohexadecane / polysorbate 80) by the company Seppic ; polymers and copolymers of 2-acrylamido-2-methylpropanesulphonic acid, optionally crosslinked and / or neutralized, such as poly (2acrylamido-2-methylpropanesulphonic acid) marketed by the company Hoechst under the trade name Hostacerin AMPS (CTFA name: ammonium polyacryldimethyltauramide) ); cellulosic derivatives such as hydroxyethylcellulose; polysaccharides and especially gums such as xanthan gum; and their mixtures.

  As lipophilic thickeners, mention may be made of synthetic polymers such as the poly C10-30 alkyl acrylate sold under the name Doresco IPA 13-1 by the company Landec, or modified clays such as hectorite and its derivatives, such as sold under the names of Bentone.

  Among the active ingredients, mention may be made of: vitamins (A, C, E, K, PP) and their derivatives or precursors, alone or in mixtures, antipollution agents and / or anti-radical agents; depigmenting agents and / or pro-pigmenting agents; anti-glycation agents; the soothing agents; the 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; the muscle-relaxing agents; tensing agents, mattifying agents, keratolytic agents, desquamating agents; the moisturizing agents; anti-inflammatory agents; agents acting on the energetic metabolism of cells; insect repellents; antagonists of substances P or CRGP.

  - anti-hair loss agents and / or hair regrowth - anti-wrinkle agents.

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

  The compositions according to the invention can be prepared according to the techniques well known to those skilled in the art. They may be in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / H or W / O / W) such as cream, milk or cream gel ; in the form of an aqueous gel; in the form of a lotion. They may optionally be packaged in aerosol and be in the form of foam or spray.

  Preferably, the compositions according to the invention are in the form of an oil-in-water or water-in-oil emulsion.

  The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W).

  As emulsifying surfactants that may be used for the preparation of W / O emulsions, mention may be made, for example, of alkyl esters or ethers of sorbitan, of glycerol or of sugars; silicone surfactants such as dimethicone copolyols such as the mixture of cyclomethicone and dimethicone copolyol, sold under the name DC 5225 C by Dow Corning, and alkyl dimethicone copolyols such as Laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid "by Dow Corning; cetyl dimethicone copolyol such as the product sold under the name Abil EM 90R by Goldschmidt and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles) and hexyl laurate sold under the name ABIL WE 09 by the company Goldschmidt. One or more coemulsifiers may also be added, which advantageously may be selected from the group consisting of alkylated polyol esters.

  Polyol alkyl esters that may especially be mentioned include polyethylene glycol esters such as PEG-30 dipolyhydroxystearate, such as the product marketed under the name Arlacel P135 by the company ICI; Examples of glycerol and / or sorbitan esters that may be mentioned are polyglycerol isostearate, such as the product sold under the name Isolan GI 34 by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI; sorbitan isostearate and glycerol, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof.

  For O / W emulsions, mention may be made, for example, as emulsifiers, of nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated) such as PEGStearate / Glyceryl Stearate sold for example by the company ICI under the name Arlacel 165; oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; fatty alcohol and sugar ethers, in particular alkylpolyglucosides (APG) such as decylglucoside and laurylglucoside sold, for example, by Henkel under the respective names Plantaren 2000 and Plantaren 1200, cetostearylglucoside optionally mixed with cetostearyl alcohol; , marketed for example under the name Montanov 68 by the company Seppic, under the name Tegocare CG90 by Goldschmidt and under the name Emulgade KE3302 by Henkel, and arachidyl glucoside, for example in the form of a mixture of arachidic and behenic alcohols and arachidylglucoside sold under the name Montanov 202 by the company Seppic. According to one 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 WO- A-92/06778.

  In the case of an emulsion, the aqueous phase thereof may comprise a nonionic 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).

  The compositions according to the invention find their application in a large number of treatments, in particular cosmetics, 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 makeup of the skin and / or lips.

  Another object of the present invention is constituted by 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, including skincare products, sunscreen products and make-up products.

  The cosmetic compositions according to the invention may for example be used as a care product and / or sun protection for the face and / or the body of liquid to semi-liquid consistency, such as lotions, milks, creams or more. less creamy, gels, gel-creams. They may optionally be packaged in aerosol and be in the form of foam or spray.

  The cosmetic compositions according to the invention may for example be used as a makeup product.

  The compositions according to the invention in the form of vaporizable fluid lotions according to the invention are applied to the skin or the hair in the form of fine particles by means of pressurizing devices. The devices according to the invention are well known to those skilled in the art and include non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and aerosol pumps using compressed air as a propellant. These are described in US Pat. Nos. 4,077,441 and 4,850,517 (which forms an integral part of the content of the description).

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

  Another subject of the invention is the use of a compound of formula (1) as defined above in a cosmetic composition as a UV radiation filtering agent, in particular as a filtering agent for UV radiation of wavelengths between 280 and 320 nm.

  Another subject of the invention is the use of a compound of formula (1) as defined above in a cosmetic composition as a control agent for the variation of the color of the skin due to UV radiation, in particular of wavelengths between 280 and 320 nm.

  Another subject of the invention is the use of a compound of formula (1) or (2) as defined above as a light-stabilizing agent for synthetic polymers such as plastics or glasses, in particular spectacle lenses or contact lenses.

  The invention will now be described with reference to the following examples given for illustrative and non-limiting. In these examples, unless otherwise indicated, the amounts are expressed as percentages by weight. The following solar formulations were carried out; the amounts are indicated in percentages by weight: EXAMPLE 1 Preparation of Diisobutyl para-acetamido benzalmalonate: Compound (a) by Route A: In a flask equipped with a Dean Stark surmounted by a condenser, a thermometer, From a stirrer, a nitrogen inlet, was placed pacetamido benzaldehyde (5 g, 0.0306 mol) and diisobutyl malonate (6.6 g, 0.0306 mol) in 25 ml of toluene. The catalyst is added: 0.18 ml of acetic acid and 0.3 ml of piperidine. The mixture is stirred under reflux and removed via Dean Stark water formed (duration 3 hours). After cooling, the precipitate formed is filtered and washed with toluene pistons, filtered and dried. 10.5 g (yield: 95% and purity> 96% by GPC) of the derivative of Example 1 in the form of an off-white powder are obtained: Mp: 114 -115 C.

  UV (Ethanol) max = 318 nm E1% = 720.

  EXAMPLE 2 Preparation of the dineopentyl para-acetamido benzalmalonate: compound (b) by route A: In a flask equipped with a Dean Stark surmounted by a condenser, a thermometer, a stirrer, an arrival of nitrogen, p-acetamido benzaldehyde (15 g, 0.0919 mol) and dineopentyl malonate (22.46 g, 0.0919 mol) were placed in 35 ml of toluene. The catalyst is added: 0.91 ml of acetic acid and 0.53 ml of piperidine. The mixture is stirred under reflux and removed via Dean Stark water formed (duration 4 hours). After cooling, the precipitate formed is filtered and washed with toluene pistons, filtered and dried. 35.5 g (yield: 99% and purity> 94% by GPC) of the derivative of Example 2 are obtained in the form of an orange-yellow solid. This product was recrystallized from isopropanol / water to give 25.2 g (Yield: 70% and 100% purity by GPC) of the derivative of Example 2 as a white solid: Mp: 184-185 vs.

  UV (Ethanol) max = 320 nm E1% = 732.

  EXAMPLE 3 Preparation of di (1,3-dimethylbutyl) para-acetamido benzalmalonate compound (c) by route A In a flask equipped with a Dean Stark surmounted by a condenser, a thermometer, a stirrer from a nitrogen inlet, p-acetamido benzaldehyde (5 g, 0.0306 mole) and di (1,3-dimethylbutyl) malonate (8.3 g, 0.0306 mole) were placed in 25 ml. ml of toluene. The catalyst is added: 0.18 ml of acetic acid and 0.3 ml of piperidine. The mixture is stirred under reflux and removed via Dean Stark water formed (duration 4 hours). After cooling, 40 ml of dichloromethane are added and the organic phase is washed twice with water. After drying and evaporation of the solvent, 6.4 g (yield: 94% and purity> 95% by GPC) of the derivative of Example 3 is obtained in the form of an orange oil. This product was purified by passage through a chromatographic column (eluent: heptane / EtOAc 80:20) to give 5.23 g (yield: 82% and purity> 99% by GPC) of the derivative of Example 3 in the form of a pale yellow oil: UV (Ethanol) max = 318 nm E1% = 695.

  EXAMPLE 4 Preparation of di (2-isopropyl-5-methylcyclohexyl) para-acetamido benzalmalonate: compound (e) by route A: (e) In a CEM Discover microwaves, the mixture is heated for 15 minutes at a temperature of 120.degree. at a power of 300 W the mixture of p-acetamido benzaldehyde (180 mg, 1.1x10-3 mol) and di (2-isopropyl-5-methylcyclohexyl) malonate (425 mg, 1.1x10-3.0306 mol) ) with 2 drops of piperidine. The red oil obtained is purified by passage through a silica column (eluent: Heptane / EtOAc 60:40) to give the derivative of Example 4 in the form of a white powder: UV (Ethanol) max = 319 nm E1% = 633.

  EXAMPLE 5 Preparation of diethyl 2-1-4- (heptadecanovlamino) benzylidenelmalonate (compound (q)) by route B: H3C- (CH2) (g) In a reactor, a mixture of para is heated under reflux for 2 hours diethylamino benzalmalonate (0.5 g, 1.73x10-3 mol), heptadecanoyl chloride (1 g, 1.73x10-3 mol) and triethylamine (0.5 ml, 1.73x10- 3 moles) in 20 ml of dichloromethane. After cooling, the organic phase is washed 3 times with water. After drying and evaporation of the solvent, the yellow solid obtained was purified by passage through a chromatographic column (eluent: CH 2 Cl 2 / EtOAc 99: 1) to give the derivative of Example 5 in the form of a white powder: PF 88-90 UV C (Ethanol) max = 320 nm E1% = 556.

  EXAMPLE 6 Preparation of diisobutyl 2-14- (heptadecanovlamino) benzylidenelmalonate (Compound (f)) by Route B: H3C- (CH2) (f) In a reactor, a mixture of para-amino is refluxed for 2 hours diisobutyl benzalmalonate (1.1 g, 3.46x10-3 mole), heptadecanoyl chloride (0.5 g, 3.46x10-3 mole) and triethylamine (0.5 ml, 3.46x10- 3 moles) in 20 ml of dichloromethane. After cooling, the organic phase is washed 3 times with water. After drying and evaporation of the solvent, the yellow solid obtained was purified by recrystallization from 95% ethanol to give the derivative of Example 6 in the form of a beige powder: mp 74-76 C UV (Ethanol) max = 321 nm E1% = 470.

  EXAMPLE 7 Preparation of diisobutyl 2-14- (pentanovlamino) benzylidenelmalonate by Route B: In a reactor, a mixture of diisobutyl para-amino benzalmalonate (3 g, 9.4x10 -3 mol) is refluxed for 2 hours. pentanoyl chloride chloride (1.15 g, 9.4x10-3 mol) and triethylamine (2.7 ml, 3.46x10-3 mol) in 30 ml of dichloromethane. After cooling, the organic phase is washed 3 times with water. After drying and evaporation of the solvent, the brown oil obtained was purified by passage through a silica column (eluent: Heptane / EtOAc 80:20) to give 2.5 g (yield: 66%) of the derivative of Example 7 in the form of a pale yellow powder: mp 60-61 ° C., UV (Ethanol) max = 321 nm E1% = 766.

  EXAMPLE 8 Preparation of di-isobutyl 2 -f4- (tetradecanovlamino) benzylidenelmalonate (compound (h)) by the route B: ## STR2 ## In reactor, a mixture is heated under reflux for 1 hour 30 minutes. diisobutyl paraamino benzalmalonate (1 g, 3.1x10-3 mole), tetradecanoyl chloride (0.77 g, 3.1x10-3 mole) and triethylamine (0.45 ml, 3.1x10- 3 moles) in 10 ml of dichloromethane. After cooling, the organic phase is washed 3 times with water. After drying and evaporation of the solvent, the yellow solid obtained was purified by passage through a silica column (eluent: Heptane / EtOAc 80:20) to give 2.5 g (yield: 66%) of the derivative of Example 7 under form of a beige powder: mp 69-70 ° C, UV (Ethanol) max = 321 nm E1% = 549.

  EXAMPLE 9 Preparation of diisobutyl para-amino benzalmalonate (compound (i)) by route D: In a flask the diisobutyl paraacetamido benzalmalonate (product of Example 1, 3 g, 0.0083 mol) was solubilized in 25 ml. ml of isopropanol. 20 ml of 2N hydrochloric acid are added thereto and the mixture is refluxed for 3 hours. After cooling, the mixture is extracted with dichloromethane and the organic phase is washed 3 times with water. After drying of the organic phase and evaporation of the solvent, 2.5 g (yield: 94% purity 96% by HPLC) of the product of Example 9 is recovered in the form of an orange-yellow solid: mp: 108 -109 vs.

  UV (ethanol) max = 358 nm E1% = 813.

  EXAMPLE 10 Preparation of the dineopentyl para-amino benzalmalonate (Compound (k)) by Route B: H 2 N (k) In a flask the dideopentyl paraacetamido benzalmalonate is solubilized (product of Example 2, 2 g, 5, 1x10 -3 mol) in 20 ml of dioxane. 1 ml of 6N hydrochloric acid is added and refluxed for 2 hours. After cooling, the mixture is extracted with dichloromethane and the organic phase is washed 3 times with water. After drying of the organic phase and evaporation of the solvents, 1.6 g (yield: 89% purity 94% by HPLC) of the product of Example 10 is recovered in the form of an orange-yellow solid: Mp: 152-153 vs.

  UV (ethanol) max = 359 nm E1% = 805.

  EXAMPLE 11: Sunscreen Composition (Oil-in-Water Emulsion) E Compound of Example 3 E Mixture of cetylstearyl alcohol and oxyethylenated cetylstearyl alcohol (33 EO units) 80/20 sold by the company Tensia under the trade name DEHSCONET 390 E Mixture of glycerol distearate monoeteal sold under the trade name CERASYNTH SD by the company ISP 2 g. Cetyl alcohol 1.5 g Polydimethylsiloxane sold under the name DC200FIuid by the company Dow Corning Glycerin 15 g Preservatives qs

  Demineralized water qsp The fatty phase is heated to approximately 70 80 C until complete melting. The aqueous phase containing the compound of Example 3 is then added with vigorous stirring all at once at 80 ° C. Stirring is maintained for 10 to 15 minutes, then it is allowed to cool with moderate stirring to approximately 40 ° C. and we add the preservatives. This gives a sun cream particularly effective against UV-B. 3g 7g

1.5 g 100 g

Claims (29)

  1. Composition containing in a cosmetically acceptable medium, characterized in that it contains at least one compound of formula (1) below: Y (1)   in which: X represents a radical R3- (C = O) -, R3-SO2- or R3-O- (C = O) -, Y represents -O- or NR4, with R4 representing hydrogen or an alkyl radical; in C 1 -C 5, linear or branched, R 1, R 2 and R 3, which are identical or different, represent a linear or branched C 1 -C 30 alkyl or C 3 -C 30 alkenyl radical which may carry one or more hydroxyl substituents and which may contain in the carbon chain an alkyl ring, one or more heteroatoms selected from oxygen, nitrogen and silicon atoms, an optionally substituted C 6 -C 20 aryl radical.   2. Composition according to claim 1, wherein the compound of formula (1) is chosen from those for which X denotes a radical R3- (C = O) -, R3-SO2- or R3-O- (C = O) - and the radicals R 1, R 2 and R 3 denote a C 1 -C 22 alkyl with the sum of the carbons present for the 3 radicals R 1, R 2 and R 3 being a number greater than or equal to 9.   3. Composition according to claim 2, wherein the compound of formula (1) is chosen from those for those for which X is R3- (C = O) -.   4. Composition according to claim 3, wherein the compound of formula (1) is chosen from among the following derivatives of formulas (a) to (i): X NH (e) H3C- (CH2) (f) H3C- (CH2) (g) NH   O H3C- (CH2) 12 // NH (h) (i) 5. Composition according to any one of claims 1 to 4, wherein the compound or compounds of formula (1) are present in proportions ranging from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight. % by weight, relative to the total weight of the composition.   6. Composition according to any one of the preceding claims, characterized in that it contains in addition to other organic or inorganic photoprotective agents active in the UV-A and / or UVB water-soluble or fat-soluble or insoluble in cosmetic solvents commonly used.   7. The composition of claim 6, wherein the complementary organic photoprotective agents are selected from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives; benzophenone derivatives; derivatives of 13, R-diphenylacrylate; benzotriazole derivatives; benzalmalonate derivatives other than those of formula (1); benzimidazole derivatives; imidazolines; bisbenzoazolyl derivatives; methylene bis (hydroxyphenyl benzotriazole) derivatives; filter polymers and silicone filters; dimers derived from alkylstyrene; 4,4-diarylbutadienes and mixtures thereof.   8. Composition according to Claim 7, characterized in that the organic UV screening agent (s) are chosen from the following compounds: Homosalate Ethylhexyl Salicylate, Ethylhexyl Methoxycinnamate Butyl Methoxydibenzoylmethane Octocrylene, Phenylbenzimidazole Sulfonic Acid, Benzophenone-3, Benzophenone-4, Benzophenone -5, 2- (4-diethylamino-2hydroxybenzoyl) -benzoate, n-hexyl ester.   4-Methylbenzylidene camphor, Camphor Benzalkonium Methosulphate Terephthalylidene Dicamphor Sulfonic Acid, Disodium Phenyl Dibenzimidazole Tetrasulfonate, 2,4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine Ethylhexyl triazone, Diethylhexylbutamido triazone, 2,4,6-tris- (4'-amino benzalmalonate diisobutyl) -s-triazine, 2,4,6-tris (4'-amino benzalmalonate dineopentyl) -s-triazine Methylene bis-Benzotriazolyl Tetramethylbutylphenol Drometrizole Trisiloxane Di-neopentyl 4'methoxybenzalmalonate Polysilicone-1,1-dicarboxy (2,2'-dimethyl-propyl) -4,4-diphenylbutadiene 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2- yl- (4phenyl) imino] -6- (2-ethylhexyl) imino-1,3,5-triazine and mixtures thereof.   9. The composition of claim 6, wherein the inorganic UV filters are pigments or nanopigments of metal oxides, treated or not.   10. Composition according to claim 9, characterized in that said pigments or nanopigments are selected from titanium oxide, zinc, iron, zirconium, cerium and mixtures thereof, treated or not.   11. Composition according to any one of the preceding claims, characterized in that it further comprises at least one agent for tanning and / or artificial browning of the skin.   12. Composition according to any one of the preceding claims, characterized in that it further comprises one or more cosmetic adjuvants chosen from fatty substances, organic solvents, ionic or nonionic thickeners, hydrophilic or lipophilic, softeners. , humectants, opacifiers, stabilizers, emollients, silicones, anti-foam agents, perfumes, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, actives, fillers, polymers, propellants, alkalinizing or acidifying agents.   13. Composition according to any one of the preceding claims, characterized in that it is in the form of an oil-in-water or water-in-oil emulsion.   14. Use of a composition as defined in any one of the preceding claims for the manufacture of products for the cosmetic treatment of skin, lips, nails, hair, eyelashes, eyebrows and / or leather scalp.   15. Use of a composition as defined in any one of the preceding claims for the manufacture of skin care products, lips, nails, hair and / or scalp.   16. Use of a composition as defined in any one of the preceding claims for the manufacture of sun protection products for lips, nails, hair and / or scalp.   17. Use of a composition as defined in any one of the preceding claims for the manufacture of makeup products.   18. Use of a compound of formula (1) as defined in the preceding claims 55 in a cosmetic composition as a UV radiation filtering agent.   19. Use of a compound of formula (1) as defined in the preceding claims in a cosmetic composition as a UV radiation filtering agent having wavelengths of between 280 and 320 nm.   20. Use of a compound of formula (1) as defined in the preceding claims in a cosmetic composition as a control agent for the variation of the color of the skin due to UV radiation, in particular of wavelengths between 280 and 320 nm.   Use of a compound of formula (1) as defined in the preceding claims as a light-stabilizing agent for synthetic polymers such as plastics or glasses, in particular spectacle lenses or contact lenses.   22. A compound of formula (1) below: Y (1) R2 / in which: X represents a radical R3- (C = O) -, R3-SO2- or R3-O- (C = O) -, Y represents -O- or NR4, with R4 representing hydrogen or a linear or branched C1-C5 alkyl radical, R1, R2 and R3, which may be identical or different, represent a C1-C30 alkyl or C3-C30 alkenyl radical, linear or branched, which may carry one or more hydroxyl substituents and which may contain in the carbon chain an alkyl ring, one or more heteroatoms chosen from oxygen, nitrogen and silicon atoms, a C 6 -C 20 aryl radical, optionally substituted with the exception of the compound of formula: 23. The compound according to claim 22, wherein the radicals R 1, R 2 and R 3 denote a C 1 -C 22 alkyl with the sum of the carbons present for the 3 radicals R 1, R 2 and R 3 being a number greater than or equal to 9.   24. A compound according to claim 23 wherein X is R3- (C = O) -. X NH   25. Compound chosen from the following derivatives of formulas (a) to (i): O   H3C- (CH2) 15 / NH (f) / OO (g) H3C- (CH2) NH (h) (i)   H3C- (CH2) 12 \ NH 26. Process for the preparation of the compounds of formula (1) as defined in claims 22 to 25, characterized in that they are obtained: a) by condensation of the para-aminobenzaldehyde of formula (2) with a chloride of acid, an anhydride, a sulphochloride or chloroformate of formula (3) in which X is a radical R3- (C = O) -, R3SO2- or R3-O- (C = O) - in which R3 has the same meaning indicated in the formula (1) defined in claims 22 to 25, to obtain the benzaldehyde compound of formula (4) corresponding followed b) a Knoevenagel reaction between the benzaldehyde of formula (4) thus obtained and a malonate compound of formula ( 5) in which Y, R, and R2 have the same meanings indicated in formula (1) defined in claims 22 to 25 according to the following reaction scheme: X   NH 'NH 0 0 + X Cl + HCI (4) (1) 27. Process for the preparation of the compounds of formula (1) as defined in claims 22 to 25, characterized in that they are obtained by condensation of an amino compound of formula (6) in which Y, R, and R2 have the same meanings indicated in the formula (1) defined above on a compound of formula (3) as defined in claim 26 according to the following reaction scheme: HCI   (6) (3) 28. Preparation process according to claim 27, wherein the amine derivatives of formula (6) are obtained: a) by Knoevenagel reaction between the para-nitro benzaldehyde of formula (7) and the malonic compound of formula (5) in wherein Y, R, and R2 have the same meanings given in formula (1) as defined in claim 26 in a solvent and in the presence of a catalyst followed b) a reduction reaction of the nitro derivative of formula ( 8) obtained with a catalyst according to the following reaction scheme: (7) R2 Reduction (8) Catalyst (9) YR ( 29. Preparation process according to claim 27, wherein the amine derivatives of formula (6) are obtained: a) by reaction of Knoevenagel between para-acetamido benzaldehyde of formula (10) and the malonic compound of formula (5) such as defined in claim 27 in a solvent and in the presence of a catalyst followed b) a simple hydrolysis in the presence of HCl and in the presence of a solvent according to the following reaction scheme: (5) Y RI + Y RI (6) Y R2 OY, R2 Hydrolysis NH + AcOH