Composition containing a large amount of inorganic UV blocking agent and organic UV blocking agent selected from organosilicon compounds having benzotriazole group

JP2024079076A5Pending Publication Date: 2025-12-09LOREAL SA
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Patent Information

Application Number
JP2022191792
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2022-11-30
Publication Date
2025-12-09

AI Technical Summary

Technical Problem

Cosmetic compositions containing large amounts of inorganic UV-screening agents, such as TiO2, often result in a squeaky texture, compromising both UV-shielding effectiveness and user comfort.

Method used

A composition comprising a combination of at least 5% inorganic UV-screening agents, preferably titanium dioxide, and 1-20% organic UV-screening agents from organosilicon compounds with benzotriazole groups, along with fatty substances and phosphate compounds, to enhance smoothness and UV protection.

Benefits of technology

The composition provides sufficient UV-shielding effects, including both UVA and UVB protection, while maintaining a smooth texture during and after application, and remains stable without crystallization of organic UV-screening agents.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide a composition capable of providing sufficient UV shielding effect and a smooth feel even when the composition contains a relatively large amount of an inorganic UV shielding agent.SOLUTION: The present invention relates to a composition containing (a) at least one inorganic UV blocking agent and (b) at least one organic UV blocking agent selected from organosilicon compounds having at least one benzotriazole group, the amount of (a) the inorganic UV blocking agent being more than 5 mass% based on the total mass of the composition. The composition according to the present invention can provide a sufficient UV blocking effect and smooth texture even when the composition contains a relatively large amount of the inorganic UV blocking agent.SELECTED DRAWING: None
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Description

[Technical field]

[0001] The present invention relates to a composition comprising a relatively large amount of an inorganic UV filter and at least one organic UV filter selected from organosilicon compounds having at least one benzotriazole group, as well as a cosmetic method using the composition, and the use of the organic UV filter in a composition comprising a relatively large amount of an inorganic UV filter. [Background technology]

[0002] Many cosmetics contain one or more UV blocking agents to block ultraviolet rays.In particular, skin cosmetics generally contain organic and / or inorganic UV blocking agents to protect skin from ultraviolet rays.Since various types of damage to skin, such as wrinkles, caused by ultraviolet rays are now well recognized, the need for UV care cosmetics is further increasing.

[0003] However, it has been found that when the composition contains a relatively large amount of an inorganic UV filter, such as TiO2, the composition tends to result in a squeaky texture. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] EP-A-0,392,882 [Patent Document 2] EP-A-0,660,701 [Patent Document 3] EP-A-0,708,108 [Patent Document 4] EP-A-0,711,778 [Patent Document 5] EP-A-711,779 [Patent Document 6] U.S. Patent No. 3,220,972 [Patent Document 7] U.S. Patent No. 3,697,473 [Patent Document 8] U.S. Patent No. 4,340,709 [Patent Document 9] U.S. Patent No. 4,316,033 [Patent Document 10] U.S. Patent No. 4,328,346 [Patent Document 11] EP-A-0,392,883 [Patent Document 12] EP-A-0,742,003 [Non-patent literature]

[0005] [Non-Patent Document 1] Cosmetics & Toiletries, February 1990, Volume 105, pp. 53-64 Summary of the Invention [Problem to be solved by the invention]

[0006] Therefore, an object of the present invention is to provide a composition that can provide sufficient UV shielding effect and smooth feel even when the composition contains a relatively large amount of an inorganic UV shielding agent. [Means for solving the problem]

[0007] The above object of the present invention is to (a) at least one inorganic UV filter; (b) at least one organic UV filter selected from organosilicon compounds having at least one benzotriazole group; A composition comprising: (a) This can be achieved by a composition, in which the amount of inorganic UV filter is more than 5% by weight, relative to the total weight of the composition.

[0008] (a) Inorganic UV filters may be selected from titanium dioxide, zinc oxide, and mixtures thereof.

[0009] The amount of (a) inorganic UV filter in the composition according to the present invention may be 20% by weight or less, preferably 15% by weight or less, more preferably 10% by weight or less, based on the total weight of the composition.

[0010] (b) The organic UV blocking agent has the formula (1): O (3-a) / 2 Si(R7) a -G (1) [In the formula, R7 is an optionally halogenated C1-C 10 an alkyl group, a phenyl group, or a trimethylsilyloxy group; a is an integer ranging from 0 to 3, inclusive; G is directly bonded to a silicon atom and has the structural formula (2):

[0011] [ka]

[0012] (In the formula, the Y groups may be the same or different and are each a C1-C8 alkyl group, a halogen atom, or a C1-C4 alkoxy group, provided that in the last case, two adjacent Y groups on the same aromatic ring may together form an alkylidene dioxy group, the alkylidene moiety having 1 or 2 carbon atoms; X is O or NH; Z is hydrogen or a C1-C4 alkyl group; n is an integer ranging from 0 to 3, inclusive; m is 0 or 1; p is an integer ranging from 1 to 10, inclusive. is a monovalent group having the formula The polyorganosiloxane may be selected from silanes and polyorganosiloxanes containing at least one structural unit having the formula:

[0013] (b) Organic UV filters have the structural formulas (5) and (6):

[0014] [ka]

[0015] [In the formula, The R7 groups may be the same or different and each may be C1 to C 10 alkyl, phenyl, 3,3,3-trifluoropropyl, or trimethylsilyloxy groups, at least 80% of the R groups being methyl groups; the D groups may be the same or different and are each an R7 group or a G group; r is an integer ranging from 0 to 50, inclusive, and s is an integer ranging from 0 to 20, inclusive, with the proviso that when s=0, at least one of the two D groups is a G group; u is an integer ranging from 1 to 6, inclusive, and t is an integer ranging from 0 to 10, inclusive, with the proviso that t+u is 3 or greater; The G group has the above structural formula (2). The compound may be selected from benzotriazole-substituted silicone compounds having any one of the following formulas:

[0016] (b) The organic UV blocking agent has the structural formula (7):

[0017] [ka]

[0018] (wherein 0≦r≦10, 1≦s≦10, and E is a divalent group:

[0019] [ka]

[0020] is) The compound may be selected from benzotriazole substituted silicone compounds having the formula:

[0021] (b) Organic UV blocking agents have the structural formula:

[0022] [ka]

[0023] The compound may be drometrizole trisiloxane having the formula:

[0024] The amount of the (b) organic UV screening agent in the composition according to the present invention may be from 1 mass % to 20 mass %, preferably from 2 mass % to 15 mass %, and more preferably from 3 mass % to 10 mass %, relative to the total mass of the composition.

[0025] The composition according to the invention may further comprise (c) at least one fatty substance.

[0026] The amount of (c) fatty substance in the composition according to the present invention may be from 1% to 20% by weight, preferably from 3% to 15% by weight, more preferably from 5% to 10% by weight, relative to the total weight of the composition.

[0027] The composition according to the present invention may further comprise (d) at least one phosphate compound.

[0028] The amount of the (d) phosphate compound in the composition according to the present invention may be 0.01% by mass to 15% by mass, preferably 0.05% by mass to 10% by mass, and more preferably 0.1% by mass to 5% by mass, relative to the total mass of the composition.

[0029] The composition according to the present invention may be a cosmetic composition, preferably a dermocosmetic composition, more preferably a skin care composition or a skin make-up composition.

[0030] The present invention also relates to a cosmetic method for keratinous substrates, such as the skin, comprising the step of applying to the keratinous substrate a composition according to the present invention.

[0031] The present invention also provides To improve the smooth texture of the composition, In a composition comprising (a) at least one inorganic UV filter in an amount of more than 5% by weight relative to the total weight of the composition, It also relates to the use of (b) at least one organic UV filter selected from organosilicon compounds carrying at least one benzotriazole group. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0032] As a result of intensive research, the present inventors have discovered that it is possible to provide a composition that can provide sufficient UV blocking effect and a smooth feel even when the composition contains a relatively large amount of an inorganic UV blocking agent.

[0033] Therefore, the composition according to the invention (a) at least one inorganic UV filter; (b) at least one organic UV filter selected from organosilicon compounds having at least one benzotriazole group; Including, (a) The amount of inorganic UV filter is more than 5% by weight, based on the total weight of the composition.

[0034] The composition according to the present invention can provide sufficient UV shielding effect and smooth feel even when the composition contains a relatively large amount of an inorganic UV shielding agent.

[0035] The composition according to the present invention can provide sufficient UV blocking effect, in particular not only UVA blocking effect but also UVB blocking effect.

[0036] The composition according to the present invention can reduce the squeaky sensation caused by a relatively large amount of (a) the inorganic UV filter in the composition.

[0037] The composition according to the present invention can provide a smooth feel during application of the composition to keratinous materials such as the skin.

[0038] The compositions according to the present invention can also provide a smooth feel even after rinsing the composition from keratinous materials such as skin.

[0039] The compositions according to the present invention are also stable such that the compositions are homogeneous or (b) free of crystals of the organic UV filter.

[0040] The compositions, methods, uses, etc. according to the present invention are described in more detail below.

[0041] [Inorganic UV blocking agent] The composition according to the invention comprises (a) at least one inorganic UV filter. When two or more inorganic UV filters are used, they may be the same or different, preferably the same.

[0042] The inorganic UV filter (a) used in the present invention may be active in the UV-A and / or UV-B region. The inorganic UV filter (a) used in the present invention is insoluble in solvents such as water and ethanol commonly used in cosmetics, but may be hydrophilic and / or lipophilic.

[0043] The (a) inorganic UV filter is preferably in the form of fine particles whose average (primary) particle diameter is in the range of 1 nm to 50 nm, preferably 5 nm to 40 nm, more preferably 10 nm to 30 nm. The average (primary) particle size or average (primary) particle diameter in this specification is the arithmetic mean diameter.

[0044] (a) The inorganic UV filter may be selected from the group consisting of silicon carbide, metal oxides which may be coated or uncoated, and mixtures thereof.

[0045] Preferably, the (a) inorganic UV filter can be selected from pigments made of metal oxides (average primary particle size: generally 5 nm to 50 nm, preferably 10 nm to 50 nm), such as pigments made of titanium oxide (amorphous or crystalline in rutile and / or anatase form), iron oxide, zinc oxide, zirconium oxide or cerium oxide, all of which are UV light protection agents known per se. Preferably, the (a) inorganic UV filter can be selected from titanium dioxide (TiO2), zinc oxide, more preferably titanium oxide.

[0046] The (a) inorganic UV filter may be coated or uncoated. The (a) inorganic UV filter may have at least one coating. The coating may comprise at least one compound selected from the group consisting of alumina, silica, aluminum hydroxide, silicone, silane, fatty acid or its salt (e.g., sodium, potassium, zinc, iron or aluminum salt), fatty alcohol, lecithin, amino acid, polysaccharide, protein, alkanolamine, wax, e.g., beeswax, (meth)acrylic polymer, organic UV filter, and (per)fluoro compound.

[0047] The coating preferably comprises at least one organic UV filter. As the organic UV filter in the coating, dibenzoylmethane derivatives, such as butyl methoxydibenzoylmethane (avobenzone) and 2,2'-methylenebis[6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethyl-butyl)phenol] (methylenebis-benzotriazolyltetramethylbutylphenol), commercially available as "TINOSORB M" by BASF, may be preferred.

[0048] As is known, the silicones in the coating may be organosilicon polymers or oligomers, including linear or cyclic and branched or crosslinked structures of various molecular weights, obtained by polymerization and / or polycondensation of suitable functional silanes, and essentially composed of main repeating units in which silicon atoms are bonded to one another through oxygen atoms (siloxane bonds) and optionally substituted hydrocarbon groups are bonded directly to said silicon atoms through carbon atoms.

[0049] The term "silicones" also includes the silanes, especially the alkylsilanes, required for their preparation.

[0050] The silicone used in the coating can be preferably selected from the group consisting of alkylsilanes, polydialkylsiloxanes, and polyalkylhydrosiloxanes. More preferably, the silicone is selected from the group consisting of octyltrimethylsilane, polydimethylsiloxane, and polymethylhydrosiloxane.

[0051] Of course, inorganic UV filters made of metal oxides may be treated with other surfacing agents, in particular cerium oxide, alumina, silica, aluminum compounds, silicon compounds, or mixtures thereof, prior to their treatment with silicone.

[0052] The coated inorganic UV filter may be prepared by subjecting the inorganic UV filter to one or more surface treatments of chemical, electronic, mechanochemical, and / or mechanical nature with any of the compounds mentioned above, as well as with polyethylene, metal alkoxides (titanium or aluminum alkoxides), metal oxides, sodium hexametaphosphate, and those shown, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, pp. 53-64.

[0053] The coated inorganic UV filter may be: Titanium oxide coated with silica, such as the product "Sunveil" manufactured by Ikeda Bussan Co., Ltd. Titanium oxide coated with silica and iron oxide, for example the product "Sunveil F" manufactured by Ikeda Bussan Co., Ltd.; Titanium dioxide coated with silica and alumina, such as the product "Microtitanium Dioxide MT 500 SA" from Teika Corporation, the product "Tioveil" from Tioxide, and the product "Mirasun TiW 60" from Rhodia; Titanium oxide coated with alumina, such as the products "Tipaque TTO-55(B)" and "Tipaque TTO-55(A)" from Ishihara Sangyo Kaisha, Ltd., and "UVT 14 / 4" from Kemira; Titanium dioxide coated with alumina and aluminum stearate, such as the products "Microtitanium Dioxide MT 100 T, MT 100 TX, MT 100 Z or MT-01" from Teika Co., the products "Solaveil CT-10 W" and "Solaveil CT 100" from Uniqema, and the product "Eusolex T-AVO" from Merck; Titanium dioxide coated with alumina and aluminum laurate, such as the product "Microtitanium Dioxide MT 100 S" from Teika Co., Ltd.; Titanium dioxide coated with iron oxide and iron stearate, such as the product "Microtitanium Dioxide MT 100 F" from Teika Co., Ltd.; Titanium oxide coated with zinc oxide and zinc stearate, such as the product "BR351" from Teika Co., Ltd. Titanium dioxide coated with silica and alumina and treated with silicone, such as the products "Microtitanium Dioxide MT 600 SAS", "Microtitanium Dioxide MT 500 SAS" and "Microtitanium Dioxide MT 100 SAS" from Teika Corporation; Titanium oxide coated with silica, alumina, and aluminum stearate and treated with silicone, such as the product "STT-30-DS" from Titan Kogyo Co., Ltd.; Titanium oxide coated with silica and treated with silicone, e.g. the product "UV-Titan X 195" from the company Kemira; Titanium oxide coated with alumina and treated with silicone, for example the product "Tipaque TTO-55(S)" from Ishihara Sangyo Kaisha or the product "UV Titan M 262" from Kemira, Titanium oxide coated with triethanolamine, such as the product "STT-65-S" manufactured by Titan Kogyo Co., Ltd. Titanium dioxide coated with stearic acid, such as the product "Tipaque TTO-55(C)" from Ishihara Sangyo Kaisha, Ltd., or Titanium dioxide coated with sodium hexametaphosphate, for example the product "Microtitanium Dioxide MT 150 W" from Teika Corporation.

[0054] Other titanium dioxide pigments treated with silicone are preferably TiO2 treated with octyltrimethylsilane and having an average individual particle size of 25 to 40 nm, such as that sold under the trademark "T 805" by the company Degussa Silices, TiO2 treated with polydimethylsiloxane and having an average individual particle size of 21 nm, such as that sold under the trademark "70250 Cardre UF TiO2Si3" by the company Cardre, and anatase / rutile TiO2 treated with polydimethylhydrosiloxane and having an average individual particle size of 25 nm, such as that sold under the trademark "Microtitanium Dioxide USP Grade Hydrophobic" by the company Color Techniques.

[0055] Preferably, the following coated TiO2 can be used as the coated inorganic UV filter: Stearic acid (and) aluminum hydroxide (and) TiO2, e.g. the product "MT-100 TV" from Teika Co., Ltd., with an average primary particle diameter of 15 nm; Dimethicone (and) stearic acid (and) aluminum hydroxide (and) TiO2, such as the product "SA-TTO-S4" manufactured by Miyoshi Kasei Co., Ltd., with an average primary particle diameter of 15 nm; Silica (and) TiO2, e.g., Teika Corporation's product "MT-100 WP", average primary particle diameter 15 nm; Dimethicone (and) silica (and) aluminum hydroxide (and) TiO2, such as the products "MT-Y02" and "MT-Y-110 M3S" manufactured by Teika Co., Ltd., with an average primary particle diameter of 10 nm; Dimethicone (and) aluminum hydroxide (and) TiO2, e.g., the product "SA-TTO-S3" manufactured by Miyoshi Kasei Co., Ltd., with an average primary particle diameter of 15 nm; Dimethicone (and) alumina (and) TiO2, for example the product "UV TITAN M170" from Sachtleben, with an average primary particle diameter of 15 nm, and Silica (and) aluminum hydroxide (and) alginate (and) TiO2, such as the product "MT-100 AQ" from Teika Co., Ltd., with an average primary particle diameter of 15 nm.

[0056] From the viewpoint of UV shielding ability, TiO2 coated with at least one organic UV shielding agent is more preferred. For example, avobenzone (and) stearate (and) aluminum hydroxide (and) TiO2, such as the product "HXMT-100ZA" manufactured by Teika Co., Ltd., with an average primary particle diameter of 15 nm, can be used.

[0057] Uncoated titanium dioxide pigments are sold, for example, by Teika under the trademarks "Microtitanium Dioxide MT500B" or "Microtitanium Dioxide MT600B", by Degussa under the trademark "P 25", by Wacker under the trademark "Oxyde de titane transparent PW", by Miyoshi Kasei Co., Ltd. under the trademark "UFTR", by Tomen under the trademark "ITS" and by Tioxide under the trademark "Tioveil AQ".

[0058] Uncoated zinc oxide pigments are, for example: Marketed under the trademark "Z-cote" by Sunsmart, Inc. Marketed under the trademark "Nanox" by Elementis, and Marketed by Nanophase Technologies under the trademark "Nanogard WCD 2025."

[0059] Coated zinc oxide pigments are, for example: one marketed by Toshiba under the trademark "Oxide Zinc CS-5" (ZnO coated with polymethylhydrosiloxane); Finsolv TN, an alkyl benzoate (C 12 ~C 15 as a 40% dispersion in those sold under the trademarks "Daitopersion Zn-30" and "Daitopersion Zn-50" by Daito Kasei Kogyo Co., Ltd. (oxyethylenated polydimethylsiloxane / cyclopolymethylsiloxane dispersions containing 30% or 50% nano zinc oxide coated with silica and polymethylhydrosiloxane); those marketed by Daikin Industries, Ltd. under the trademark "NFD Ultrafine ZnO" (ZnO coated with perfluoroalkyl phosphate and perfluoroalkylethyl based copolymers as a cyclopentasiloxane dispersion); one marketed by Shin-Etsu Chemical Co., Ltd. under the trademark "SPD-Z1" (ZnO coated with silicone-grafted acrylic polymer dispersed in cyclodimethylsiloxane); Marketed by ISP under the trademark "Escalol Z100" (alumina-treated ZnO dispersed in an ethylhexyl methoxycinnamate / PVP-hexadecene copolymer / methicone mixture); The one sold by Fuji Pigment Co., Ltd. under the trademark "Fuji ZnO-SMS-10" (ZnO coated with silica and polymethylsilsesquioxane) and the one sold by Elementis under the trademark "Nanox Gel TN" (alkyl benzoate (C ) containing hydroxystearic acid polycondensate) 12 ~C 15 ) with 55% dispersion of ZnO.

[0060] Uncoated cerium oxide pigments are, for example, sold under the trademark "Colloidal Cerium Oxide" by the company Rhone-Poulenc.

[0061] Uncoated iron oxide pigments are sold, for example, by the company Arnaud under the trademarks "Nanogard WCD 2002 (FE 45B)", "Nanogard Iron FE 45 BL AQ", "Nanogard FE 45R AQ" and "Nanogard WCD 2006 (FE 45R)" or by the company Mitsubishi under the trademark "TY-220".

[0062] Coated iron oxide pigments are sold, for example, by the company Arnaud under the trademarks "Nanogard WCD 2008 (FE 45B FN)", "Nanogard WCD 2009 (FE 45B 556)", "Nanogard FE 45 BL 345" and "Nanogard FE 45 BL" or by the company BASF under the trademark "Oxyde de fer transparent".

[0063] Mention may also be made of mixtures of metal oxides, in particular mixtures of titanium dioxide and cerium dioxide, such as the equal weight mixture of titanium dioxide coated with silica and cerium dioxide coated with silica sold under the trademark "Sunveil A" by Ikeda Bussan Co., Ltd., and also mixtures of titanium dioxide and zinc dioxide coated with alumina, silica and silicone, such as the product "M 261" sold by Kemira, or mixtures of titanium dioxide and zinc dioxide coated with alumina, silica and glycerol, such as the product "M 211" sold by Kemira.

[0064] The coated inorganic UV filter is preferred because it can enhance the UV-shielding effect of the inorganic UV filter. In addition, the coating can be useful for dispersing the UV filter uniformly or homogeneously in the composition according to the present invention.

[0065] The amount of (a) inorganic UV filter in the composition according to the present invention is more than 5% by weight, preferably 6% by weight or more, more preferably 7% by weight or more, based on the total weight of the composition.

[0066] The amount of (a) inorganic UV filter in the composition according to the present invention may be 20% by weight or less, preferably 15% by weight or less, more preferably 10% by weight or less, based on the total weight of the composition.

[0067] The amount of the (a) inorganic UV screening agent in the composition according to the present invention may be more than 5 mass % and not more than 20 mass %, preferably 6 mass % to 15 mass %, and more preferably 7 mass % to 10 mass %, based on the total mass of the composition.

[0068] [Organic UV blocking agent] The composition according to the present invention comprises at least one organic UV filter selected from (b) organosilicon compounds having at least one benzotriazole group.When two or more organic UV filters are used, they may be the same or different, and preferably the same.

[0069] (b) The organic UV filter is selected from organosilicon compounds having at least one benzotriazole group.

[0070] The organosilicon compound having at least one benzotriazole group is represented by the following formula (1): O (3-a) / 2 Si(R7) a -G (1) [In the formula, R7 is optionally halogenated, C1-C 10 represents an alkyl group, a phenyl group, or a trimethylsilyloxy group; - a represents an integer ranging from 0 to 3 (inclusive); - G is directly bonded to a silicon atom and has the following structural formula (2):

[0071] [ka]

[0072] (In the formula, - the Y groups, which may be the same or different, are each a C1-C8 alkyl group, a halogen atom, or a C1-C4 alkoxy group, with the proviso that in the last case, two adjacent Y groups on the same aromatic ring may together form an alkylidene dioxy group, the alkylidene moiety having 1 or 2 carbon atoms, - X is O or NH, - Z is hydrogen or a C1-C4 alkyl group; - n is an integer ranging from 0 to 3, inclusive; m is 0 or 1, - p is an integer ranging from 1 to 10, inclusive. represents a monovalent group having the formula The compound may be a silane or siloxane having a benzotriazole functional group that contains at least one structural unit of

[0073] These compounds are described, inter alia, in EP-A-0,392,882, EP-A-0,660,701, EP-A-0,708,108, EP-A-0,711,778 and EP-A-711,779.

[0074] The organosilicon compound having at least one benzotriazole group may preferably belong to the general family of benzotriazole silicones, which are described in particular in EP-A-0,660,701.

[0075] One family of particularly preferred benzotriazole silicones according to the present invention has the following structural formula (5) or (6):

[0076] [ka]

[0077] [In the formula, R7 groups may be the same or different and each may be C1 to C 10 alkyl, phenyl, 3,3,3-trifluoropropyl or trimethylsilyloxy groups, at least 80% of the R groups being methyl groups; - the D groups, which may be the same or different, are each an R7 group or a G group, - r is an integer ranging from 0 to 50, inclusive, and s is an integer ranging from 0 to 20, inclusive, with the proviso that if s=0, then at least one of the two D groups is a G group; - u is an integer between 1 and 6, inclusive, and t is an integer between 0 and 10, inclusive, with the proviso that t+u is 3 or greater; The G group has the above structural formula (2). It is a family that contains compounds corresponding to:

[0078] As can be seen from the formula (2) given above, the divalent group -(X) m -(CH2) pThe -CH(Z)-CH2- bond thus ensures a direct bond of the benzotriazole group to the silicon atom, but the two aromatic rings of benzotriazole:

[0079] [ka]

[0080] The position may be at any available position.

[0081] Preferably, this bond is at the 3, 4, 5 position (the aromatic ring carrying the hydroxyl functionality) or the 4' position (the benzene ring adjacent to the triazole ring), even more preferably at the 3, 4 or 5 position. In a more preferred embodiment of the invention, the bond is at the 3 position.

[0082] Similarly, attachment of the substituent unit Y may be at any other available position on the benzotriazole. However, preferably, this attachment is at the 3, 4, 4', 5 and / or 6 positions. In a more preferred embodiment of the invention, attachment of the Y group is at the 5 position.

[0083] In the above formulas (5) and (6), the alkyl group may be linear or branched, and is in particular selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl and tert-octyl. Preferred alkyl groups R7 according to the invention are methyl, ethyl, propyl, n-butyl, n-octyl and 2-ethylhexyl. Even more preferably, all R7 groups are methyl.

[0084] Among the compounds of formula (5) or (6) above, the compounds corresponding to formula (5), ie diorganosiloxanes containing short linear chains, are preferred.

[0085] Among the compounds of formula (5) above, those in which both D groups are R7 groups are preferred.

[0086] Among the linear diorganosiloxanes according to formula (5), more particular preference is given to random or well-defined block derivatives which have at least one, and even more preferably all, of the following characteristics: - D is an R7 group, R7 is an alkyl group, even more preferably methyl; - r is in the range of 0 to 15, inclusive; - s is in the range of 1 to 10, inclusive; - n is other than zero and preferably equal to 1, and Y is a methyl group, a tert-butyl group or a C1-C4 alkoxy group, Z is hydrogen or methyl; m=0 or [m=1 and X=0], - p equals 1.

[0087] One family of particularly suitable benzotriazole silicones according to the present invention has the following structure (7):

[0088] [ka]

[0089] (In the formula, 0≦r≦10 and 1≦s≦10; E is a divalent group:

[0090] [ka]

[0091] is) It has the following characteristics.

[0092] In a particularly preferred embodiment of the present invention, the benzotriazole silicone has the following structural formula:

[0093] [ka]

[0094] The corresponding compound is drometrizole trisiloxane (CTFA name).

[0095] Suitable processes for the preparation of the compounds of formulae (1), (5), (6) and (7) above are described, inter alia, in U.S. Pat. Nos. 3,220,972, 3,697,473, 4,340,709, 4,316,033 and 4,328,346, and also in EP-A-0,392,883 and EP-A-0,742,003.

[0096] The amount of the (b) organic UV filter in the composition according to the present invention may be 1% by weight or more, preferably 2% by weight or more, more preferably 3% by weight or more, based on the total weight of the composition.

[0097] The amount of (b) the organic UV filter in the composition according to the present invention may be 20% by weight or less, preferably 15% by weight or less, more preferably 10% by weight or less, based on the total weight of the composition.

[0098] The amount of the (b) organic UV screening agent in the composition according to the present invention may be from 1 mass % to 20 mass %, preferably from 2 mass % to 15 mass %, and more preferably from 3 mass % to 10 mass %, relative to the total mass of the composition.

[0099] [fatty substances] The composition according to the invention may comprise (c) at least one fatty substance. If two or more fatty substances are used, these may be the same or different.

[0100] The term "fatty substance" refers to an organic compound that is insoluble in water (solubility less than 5%, preferably less than 1%, and more preferentially less than 0.1%) at room temperature (25°C) and atmospheric pressure (760 mmHg). Fatty substances may contain in their structure at least two consecutive siloxane groups or at least one hydrocarbon-based chain containing at least 6 carbon atoms. In addition, fatty substances may be soluble in organic solvents, such as chloroform, ethanol, benzene or decamethylcyclopentasiloxane, under the same temperature and pressure conditions.

[0101] It should be noted that within the scope of the present invention, the fatty substances do not contain any C2-C3 oxyalkylene units or any glycerolated units.

[0102] (c) The fatty material may be in liquid or solid form. As used herein, "liquid" and "solid" refer to the fatty material that is at atmospheric pressure (760 mmHg or 10 5 This means that the (c) fatty substance is in the form of a liquid or a paste (non-solid), or in the form of a solid, at room temperature (25° C.) under atmospheric pressure (at 25° C.). It is preferred that the (c) fatty substance comprises at least one fatty substance which is in the form of a liquid or a paste, preferably in the form of a liquid, at room temperature and atmospheric pressure. A (c) fatty substance which is in the form of a liquid at room temperature and atmospheric pressure may be referred to as an "oil". It is preferred that the (c) fatty substance is selected from oils.

[0103] (c) When the fatty substance is chosen from oils, the composition according to the invention may have an oily phase.

[0104] When the (c) fatty substance is selected from oils, the (c) fatty substance may be selected from polar oils, non-polar oils, and mixtures thereof. It is preferred that the (c) fatty substance is selected from polar oils.

[0105] The (c) fatty substance can be selected from the group consisting of oils of animal or vegetable origin, mineral oils, synthetic glycerides, esters of fatty alcohols and / or fatty acids other than animal or vegetable oils and synthetic glycerides, fatty alcohols, fatty acids, silicone oils, and hydrocarbons. These fatty substances may be volatile or non-volatile. Preferably, the (c) fatty substance is selected from the group consisting of oils of animal or vegetable origin, synthetic glycerides, fatty esters other than animal or vegetable oils and synthetic glycerides, fatty alcohols, fatty acids, silicone oils, and hydrocarbons. More preferably, the (c) fatty substance is selected from silicones and hydrocarbons, preferably aliphatic hydrocarbons, more preferably mineral oils, and mixtures thereof.

[0106] Examples of aliphatic hydrocarbons include, for example, linear or branched hydrocarbons such as mineral oils (e.g., liquid paraffin), paraffin, petrolatum or petrolatum, naphthalene, etc.; hydrogenated polyisobutene, isoeicosane, polydecene, hydrogenated polyisobutenes such as Parleam, and decene / butene copolymers; and mixtures thereof.

[0107] Examples of other aliphatic hydrocarbons include linear or branched, or optionally cyclic, C6-C 16 Mention may also be made of lower alkanes. Examples that may be mentioned are hexane, undecane, dodecane, tridecane, and isoparaffins, such as isohexadecane and isodecane.

[0108] As examples of synthetic glycerides, mention may be made, for example, of caprylic / capric triglycerides, such as those sold by the company Stearineries Dubois or under the names Miglyol® 810, 812 and 818 by the company Dynamit Nobel.

[0109] Examples of silicone oils include linear organopolysiloxanes such as dimethylpolysiloxane or dimethicone, methylphenylpolysiloxane, methylhydrogenpolysiloxane, etc.; cyclic organopolysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, etc.; and mixtures thereof.

[0110] Examples of vegetable oils include, for example, linseed oil, camellia oil, macadamia nut oil, sunflower oil, apricot oil, soybean oil, arara oil, hazelnut oil, corn oil, mink oil, olive oil, avocado oil, camellia oil, castor oil, safflower oil, jojoba oil, almond oil, grape seed oil, sesame oil, peanut oil, and mixtures thereof.

[0111] Examples of animal oils include, for example, squalene, perhydrosqualene, and squalane.

[0112] Examples of esters of fatty acids and / or fatty alcohols, advantageously different from the abovementioned animal or vegetable oils and synthetic glycerides, are in particular saturated or unsaturated, linear or branched C1-C 26 Aliphatic mono- or polyacids and saturated or unsaturated, linear or branched C1-C 26 Mention may be made of esters with aliphatic mono- or polyalcohols, the total carbon number of the ester being 10 or more.

[0113] Among the monoesters, dihydroabietyl behenate; octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 ~C 15Alkyl lactates;Isostearyl lactate;Lauryl lactate;Linoleyl lactate;Oleyl lactate;Isostearyl octanoate;Isocetyl octanoate;Octyl octanoate;Cetyl octanoate;Decyl oleate;Isocetyl isostearate;Isocetyl laurate;Isocetyl stearate;Isodecyl octanoate;Isodecyl oleate;Isononyl isononanoate;Isostearyl palmitate;Methylacetyl ricinoleate;Myristyl stearate;Octyl isononanoate;2-Ethylhexyl isononanoate;Octyl palmitate;Octyl pelargonate;Stearate Examples of suitable alkyl esters include octyl myristate, octyldodecyl erucate, oleyl erucate, ethyl and isopropyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl myristate, butyl myristate, cetyl myristate, 2-octyldodecyl myristate, myristyl myristate, and stearyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, and 2-hexyldecyl laurate.

[0114] In relation to this variant, C4~C 22 Dicarboxylic or tricarboxylic acids and C1-C 22 Esters with alcohols, and mono-, di- or tricarboxylic acids with C2-C 26 Esters of with di-, tri-, tetra- or pentahydroxy alcohols can also be used.

[0115] In particular, the following may be mentioned: diethyl sebacate, diisopropyl sebacate, diisopropyl adipate, di-n-propyl adipate, dioctyl adipate, diisostearyl adipate, dioctyl maleate, glyceryl undecylenate, octyldodecyl stearoyl stearate, pentaerythrityl monoricinoleate, pentaerythrityl tetraisononanoate, pentaerythrityl tetrapelargonate, pentaerythrityl tetraisostearate. glyceryl stearate, glyceryl tristearate, glyceryl trioctanoate, trioctyldodecyl citrate, trioleyl citrate, propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate, and polyethylene glycol distearate.

[0116] Of the esters mentioned above, preference is given to using ethyl palmitate, isopropyl palmitate, myristyl palmitate, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl myristate, butyl myristate, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate, dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.

[0117] The composition contains, as the fatty ester, C6 to C 30 , preferably C 12 ~C 22 Sugar esters and diesters of fatty acids may also be included. The term "sugar" refers to oxygen-bearing hydrocarbon-based compounds containing at least four carbon atoms, with or without aldehyde or ketone functional groups, and with some alcohol functional groups. These sugars may be monosaccharides, oligosaccharides or polysaccharides.

[0118] Examples of suitable sugars that may be mentioned are sucrose (or saccharose), glucose, galactose, ribose, fructose, maltose, mannose, arabinose, xylose and lactose, as well as derivatives thereof, in particular alkyl derivatives such as methyl derivatives, e.g. methylglucose.

[0119] Sugar esters of fatty acids are those that are made by mixing the sugars described above with linear or branched, saturated or unsaturated, C6-C 30 , preferably C 12 ~C 22 They may in particular be selected from the group comprising the esters or mixtures of esters with fatty acids. When the sugar esters of fatty acids are unsaturated, these compounds may contain from 1 to 3 conjugated or non-conjugated carbon-carbon double bonds.

[0120] The esters according to this variant may also be chosen from mono-, di-, tri-, tetraesters and polyesters, and mixtures thereof.

[0121] These esters may be chosen, for example, from oleic, lauric, palmitic, myristic, behenic, coconut, stearic, linoleic, linolenic, capric and arachidonic esters, or mixtures thereof, such as, in particular, mixed oleo-palmitic, oleo-stearic and palmito-stearic esters.

[0122] More particularly, it is preferred to use monoesters and diesters, in particular the mono- or dioleate, stearate, behenate, oleopalmitate, linoleate, linolenate and oleostearate of sucrose, glucose or methylglucose.

[0123] An example that may be mentioned is the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.

[0124] Examples of esters or mixtures of esters of sugars and fatty acids that may also be mentioned are: - products sold by Crodesta under the names F160, F140, F110, F90, F70 and SL40, which represent sucrose palmitostearate formed respectively from 73% monoesters and 27% di- and triesters, 61% monoesters and 39% di- and triesters, triesters and tetraesters, 52% monoesters and 48% di- and triesters, triesters and tetraesters, 45% monoesters and 55% di- and triesters, triesters and tetraesters, 39% monoesters and 61% di- and triesters, triesters and tetraesters, and sucrose monolaurate; - the products sold under the name Ryoto Sugar Esters, referenced for example in B370 and corresponding to sucrose behenate formed from 20% monoester and 80% di-triester-polyester; - sucrose mono-dipalmito-stearate sold under the name Tegosoft® PSE by the company Goldschmidt.

[0125] The fatty substance may be at least one fatty acid, and two or more fatty acids may be used. The fatty acids should be in acidic form (i.e. not salified, to avoid soap), may be saturated or unsaturated, contain 6 to 30 carbon atoms, in particular 9 to 30 carbon atoms, and are optionally substituted, in particular with one or more (in particular 1 to 4) hydroxyl groups. When the fatty acids are unsaturated, these compounds may contain 1 to 3 conjugated or non-conjugated carbon-carbon double bonds. The fatty acids are more particularly selected from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid. Preferably, the fatty substance is not a fatty acid.

[0126] The fatty material may be at least one fatty alcohol, and two or more fatty alcohols may be used.

[0127] The term "aliphatic alcohol" as used herein refers to any saturated or unsaturated, linear or branched C-C 30 By aliphatic alcohols is meant, in particular, optionally substituted with one or more, in particular 1 to 4, hydroxyl groups. When the aliphatic alcohols are unsaturated, these compounds may contain 1 to 3 conjugated or non-conjugated carbon-carbon double bonds.

[0128] C8~C 30 Among the aliphatic alcohols, for example, C 12 ~C 22 Fatty alcohols are used. Among them, mention may be made of lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, myristyl alcohol, arachidonyl alcohol and erucyl alcohol and mixtures thereof. In one embodiment, cetyl alcohol, stearyl alcohol or mixtures thereof (e.g. cetearyl alcohol) and myristyl alcohol can be used as solid fatty substances. In another embodiment, isostearyl alcohol can be used as liquid fatty substances.

[0129] The fatty substance may be a wax. In this specification, "wax" means that the fatty substance is in a substantially solid form at room temperature (25° C.) under atmospheric pressure (760 mmHg) and generally has a melting point of 35° C. or higher. As the waxy fatty substance, waxes generally used in cosmetics can be used alone or in combination.

[0130] For example, waxes include carnauba wax, microcrystalline wax, ozokerite, hydrogenated jojoba oil, polyethylene waxes, such as the wax sold under the name "Performalene 400 Polyethylene" by New Phase Technologies, silicone waxes, e.g. poly(C 24 ~C 28 ) alkylmethyldimethylsiloxanes, for example the product sold under the name "Abil Wax 9810" by the company Goldschmidt, palm fat, alkyl stearates (C ) sold under the name "Kester Wax K82H" by the company Kester Keunen 20 ~C 40 ), stearyl benzoate, shellac wax, and mixtures thereof. For example, waxes selected from carnauba wax, candelilla wax, ozokerite, hydrogenated jojoba oil, and polyethylene wax can be used. In at least one embodiment, the wax is preferably selected from candelilla wax and ozokerite, and mixtures thereof.

[0131] (c) The fatty material is preferably selected from ester oils, fatty alcohols, and mixtures thereof. More preferably, the ester oil is selected from monoesters, diesters, and mixtures thereof in the form of oils.

[0132] The amount of (c) fatty material in the composition according to the present invention may be 1% by weight or more, preferably 3% by weight or more, more preferably 5% by weight or more, relative to the total weight of the composition.

[0133] The amount of (c) fatty material in the composition according to the invention may be up to 20% by weight, preferably up to 15% by weight, more preferably up to 10% by weight, relative to the total weight of the composition.

[0134] The amount of (c) fatty substance in the composition according to the present invention may be from 1% to 20% by weight, preferably from 3% to 15% by weight, more preferably from 5% to 10% by weight, relative to the total weight of the composition.

[0135] [Phosphate compounds] The composition according to the present invention comprises (d) at least one phosphate compound. Two or more (d) phosphate compounds may be used in combination. Thus, a single type of phosphate compound or a combination of different types of phosphate compounds may be used.

[0136] The term "phosphate compound" as used herein means a compound having at least one phosphate group.

[0137] A "phosphate compound" may have at least one phosphate group, in particular one phosphate group.

[0138] The phosphate compound may be selected from organic phosphates, inorganic phosphates and mixtures thereof.

[0139] The inorganic phosphate may preferably be selected from inorganic salts of phosphoric acid, such as metal or ammonium salts of phosphoric acid.

[0140] The inorganic phosphate may be more preferably in the form of a metal salt. The metal salt may be an alkali metal salt. The alkali metal salt may be selected from the alkali metal salt of phosphoric acid, such as mono-, di- or trisodium phosphate, and mono-, di- or tripotassium phosphate. Dipotassium phosphate may be even more preferably.

[0141] It may also be preferred that the organophosphate is selected from esters of phosphoric acid, such as mono-, di- or tri-organophosphates.

[0142] According to one embodiment, the (d) phosphate compound may be selected from the group consisting of:

[0143] (1) A compound of formula (XIV):

[0144] [ka]

[0145] [R1, R2 and R3 may be the same or different and are as follows: the OM group (M represents an alkali metal, for example Na, Li or K, preferably Na or K); OR4 group, where R4 is a linear, branched, cyclic or aromatic C5-C 40 Alkyl groups, preferably C 12 ~C 20 Alkyl groups, more preferably C 16 Or C 18 represents an alkyl group), OH groups, and Oxyethylene group (OCH2CH2) n (OCH2CHCH3) m OR (R is a hydrogen atom or a linear or branched C1-C 20 Alkyl groups, e.g., C5-C 18 and C 12 ~C 15 represents an alkyl group, n and m are integers, n is in the range of 1 to 50 or is equal to 10, and m is in the range of 0 to 50 or is equal to 0. selected from], (2) glycerophospholipids, and (3) Mixtures of these.

[0146] In the above formula (XIV), at least one of R1, R2 and R3 is an -OM group, and at least one of R1, R2 and R3 is an -OR4 group or -(OCH2CH2) n (OCH2CH(CH3)) m It may be preferred that n is OR, where n and m have the meanings as defined above.

[0147] In the above formula (XIV), at least one of R1, R2 and R3 is an -OM group, at least one of R1, R2 and R3 is an -OH group, and at least one of R1, R2 and R3 is an -OR4 group or -(OCH2CH2) n (OCH2CH(CH3)) m It may be preferred that n is OR, where n and m have the meanings as defined above.

[0148] In the above formula (XIV), one of R1, R2 and R3 is an -OM group, one of R1, R2 and R3 is an -OH group, and one of R1, R2 and R3 is an -OR4 group or -(OCH2CH2) n (OCH2CH(CH3)) m It may be preferred that n is OR, where n and m have the meanings as defined above.

[0149] In addition, in the above formula (XIV), at least one, two or all of the R1, R2 and R3 groups are -OR4 groups (wherein R4 is a linear or branched C 10 ~C 30 , especially C 15 ~C 20 Or even C 16 Or C 18 In some cases, it may be preferable to include R1, R2 and R3, which represent an alkyl group. In this case, R1, R2 and R3 may be the same or different.

[0150] Non-limiting examples of these compounds of formula (XIV) include, for example, trioleyl phosphate, e.g., Nikkol TDP, sold by Nikko Chemicals Co., Ltd., an ether of phosphoric acid, ethylene glycol, and C 12 ~C 15 Mixture of triesters with fatty alcohols (approximately 10 EO) (INCI name: Tri-C 12~15Pareth-10 phosphate), such as Nikkol TDP-10 sold by Nikko Chemicals Co., potassium cetyl phosphate, such as Amphisol K sold by DSM Nutritional Products or Arlatone MAP 160 K from Uniqema, and ceteth-10 phosphate, such as Protaphos CET-10 by Protameen Chemicals, may be mentioned.

[0151] It may be preferable that the (d) phosphate compound has a surfactant function, and therefore the (d) phosphate compound may be a phosphate surfactant.

[0152] (d) The phosphate compound may be selected from the group consisting of monoester phosphates of alkoxylated fatty alcohols containing 12 to 20 carbon atoms having an alkylene oxide selected from 1 to 50 moles of ethylene oxide and propylene oxide, and dialkyl phosphates of non-alkoxylated alcohols containing 12 to 22 carbon atoms, and mixtures thereof. The alkyl moiety of the fatty alcohol or non-alkoxylated alcohol may be a linear or branched, or saturated or unsaturated alkyl group.

[0153] (d) The phosphate compound may be selected from the group consisting of a combination of ceteth-10 phosphate and dicetyl phosphate, a combination of ceteth-20 phosphate and dicetyl phosphate, and a combination of oleth-5 phosphate and dioleyl phosphate.

[0154] A product containing a combination of ceteth-10 phosphate and dicetyl phosphate can be CRODAFOS CES, marketed by Croda Inc. USA. A product containing a combination of ceteth-20 phosphate and dicetyl phosphate can be CRODAFOS CS-20 ACID, marketed by Croda Inc. USA. A product containing a combination of oleth-5 phosphate and dioleyl phosphate can be CRODAFOS HCE, marketed by Croda Inc. USA.

[0155] For the purposes of the present invention, the term "glycerophospholipid" is intended to mean an ester obtained by reacting glycerol with at least one saturated or unsaturated fatty acid and with phosphoric acid, said phosphoric acid being substituted with an alcohol bearing an amine function, in particular a compound chosen from β-aminoalcohols, which may be chosen, for example, from choline, ethanolamine and / or serine.

[0156] Glycerophospholipids have the following general formula (XV):

[0157] [ka]

[0158] [In the formula, R1 and R2, independently of one another, represent a saturated or unsaturated, optionally branched fatty acid containing from 4 to 24 carbon atoms and optionally substituted with one or more hydroxyl and / or amine functional groups; X is a group of the general formula R3R4R5N + -CH(R6)-CH2- (wherein R3, R4, R5 and R6 each independently represent a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, and / or a carboxyl functional group) substituent). X may in particular be chosen from choline, serine and ethanolamine.

[0159] According to one embodiment, R1 and R2, independently of one another, are advantageously chosen from butyric acid, caproic acid, caprylic acid, capric acid, caproleic acid, lauric acid, lauroleic acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, arachidic acid, isostearic acid, dihydroxystearic acid and ricinoleic acid.

[0160] The glycerophospholipid may also be a mixture of compounds of general formula (XV).

[0161] Glycerophospholipids suitable for use in the present invention may include, for example, phosphatidylcholine, phosphatidylethanolamine, and / or phosphatidylserine.

[0162] According to one embodiment, the glycerophospholipid may comprise an ester of glycerol, an unsaturated fatty acid, phosphoric acid, and choline (also known as phosphatidylcholine (PC)).

[0163] Glycerophospholipids suitable for use in the present invention may be derived from lecithin, which may contain primarily phosphatidylcholine as the glycerophospholipid.

[0164] Phosphatidylcholines (PC) suitable for use in the compositions according to the invention may be of "natural" or "synthetic" origin.

[0165] "Natural" PC can be obtained by extraction from animal or plant sources, e.g., soybean, sunflower or egg. Naturally obtained non-hydrogenated phosphatidylcholine, e.g., from soybean, generally contains, as glycerol-esterified fatty acids, palmitic acid, stearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid and optionally C 20 ~C 22 Contains fatty acids.

[0166] For the purposes of the present invention, the term "synthetic phosphatidylcholine" is intended to mean a phosphatidylcholine that contains at least one fatty acid different from that which may be present in natural PC.

[0167] The term "synthetic PC" is also intended to mean naturally occurring PC that has been modified, such as by partial hydrogenation, i.e., maintaining only some of the double bonds present in the unsaturated fatty acids.

[0168] Among the sources of more or less purified phosphatidylcholine suitable for use in the cosmetic composition according to the invention, mention may be made of Emulmetik 930 sold by the company Lucas Meyer.

[0169] The glycerophospholipids suitable for use in the present invention can be introduced into the composition in the form of lecithin, which is generally obtained by lipid extraction from plant or animal fats using non-polar solvents. This lipid fraction usually contains mainly glycerophospholipids containing phosphatidylcholine or phosphatidylethanolamine.

[0170] Lecithins suitable for use in the present invention may be soy-, sunflower- or egg-derived lecithins, and / or mixtures thereof.

[0171] Lecithin is usually provided in dissolved form in fatty acids, triglycerides or other solvents, or in the form of a powder or cake.

[0172] Lecithin is typically a mixture of lecithins with the glycerophospholipid content in commercially available products generally ranging from at least about 15% to at least about 95%.

[0173] In an exemplary embodiment, the lecithin used as starting material for the preparation of a composition according to the invention comprises at least 45% by weight, such as at least 65% by weight, such as at least 75% by weight, such as at least 85% by weight, or such as at least 95% by weight, of glycerophospholipids, based on the total weight of the lecithin.

[0174] Among the lecithins that may be suitable for use in the cosmetic composition according to the invention, mention may be made of the lecithins sold under the references Nattermann Phospholipid®, Phospholipon 80® and Phosale 75® by the American Lecithin Company, and Epikuron 145V, Topcithin 300, Emulmetik 930 and Ovothin 200 by the company Lucas Meyer.

[0175] The glycerophospholipids may be non-hydrogenated glycerophospholipids, i.e. esters obtained by reacting glycerol with at least one unsaturated fatty acid and with phosphoric acid, the phosphoric acid being substituted with an alcohol having an amine function, in particular a compound selected from β-amino alcohols.

[0176] The terms "unsaturated" and "unsaturated" are intended to mean the presence of at least one, or even several, double or triple bonds between two carbon atoms.

[0177] The glycerophospholipid may be a phosphatidylcholine or a lecithin.

[0178] (d) The phosphate compound is trioleyl phosphate, an ether of phosphoric acid, ethylene glycol, and C 12 ~C 15 They may be selected from mixtures of triesters with fatty alcohols (about 10 EO), potassium cetyl phosphate, ceteth-10 phosphate, dipotassium phosphate, cetyl phosphate and lecithin, and mixtures thereof.

[0179] (d) The phosphate compound is a non-ionic surfactant, such as trioleyl phosphate, or an ether of phosphoric acid, ethylene glycol, and C 12 ~C 15 It may also be a mixture of triesters with aliphatic alcohols (about 10 EO).

[0180] The amount of the (d) phosphate compound in the composition according to the present invention may be 0.01% by mass or more, preferably 0.05% by mass or more, and more preferably 0.1% by mass or more, based on the total mass of the composition.

[0181] The amount of (d) the phosphate compound in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, more preferably 5% by weight or less, based on the total weight of the composition.

[0182] The amount of the (d) phosphate compound in the composition according to the present invention may be 0.01% by mass to 15% by mass, preferably 0.05% by mass to 10% by mass, and more preferably 0.1% by mass to 5% by mass, relative to the total mass of the composition.

[0183] [water] The composition according to the present invention may include (e) water.

[0184] The amount of (e) water in the composition according to the present invention may be 40% by mass or more, preferably 45% by mass or more, more preferably 50% by mass or more, based on the total mass of the composition.

[0185] On the other hand, the amount of (e) water in the composition according to the present invention may be 90% by mass or less, preferably 85% by mass or less, and more preferably 80% by mass or less, based on the total mass of the composition.

[0186] The amount of (e) water in the composition according to the present invention may be within the range of 40% by mass to 90% by mass, preferably 45% by mass to 85% by mass, and more preferably 50% by mass to 80% by mass, relative to the total mass of the composition.

[0187] [Optional ingredients] The composition according to the present invention may contain at least one optional component typically used in cosmetics, specifically, for example, a dye, a filler, a surfactant, or an emulsifier other than component (d), a thickener, a film-forming polymer, a natural extract derived from an animal or a plant, etc., within a range that does not impair the effects of the present invention.

[0188] The compositions according to the invention may comprise one or several cosmetically acceptable organic solvents, which may be alcohols, in particular monohydric alcohols, such as ethyl alcohol, isopropyl alcohol, benzyl alcohol, and phenylethyl alcohol; diols, such as ethylene glycol, propylene glycol and caprylyl glycol; other polyols, such as glycerol; and ethers, such as ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol monomethyl, monoethyl and monobutyl ether, and butylene glycol monomethyl, monoethyl and monobutyl ether.

[0189] The amount of organic solvent in the composition according to the invention may be 0.01% by weight or more, preferably 0.1% by weight or more, more preferably 1% by weight or more, relative to the total weight of the composition.

[0190] On the other hand, the amount of organic solvent in the composition according to the present invention may be 30% by weight or less, preferably 25% by weight or less, more preferably 20% by weight or less, relative to the total weight of the composition.

[0191] Therefore, the amount of organic solvent in the composition according to the present invention may be in the range of 0.01% by mass to 30% by mass, preferably 0.1% by mass to 25% by mass, and more preferably 1% by mass to 20% by mass, relative to the total mass of the composition.

[0192] [Preparation] The composition according to the present invention can be prepared by mixing the essential components described above and, where necessary, the optional components described above.

[0193] The method and means for mixing the above essential components and optional components are not limited. Any conventional method and means can be used to mix the above essential components and optional components to prepare the composition according to the present invention.

[0194] [form] The form of the composition according to the present invention is not limited.

[0195] The composition according to the present invention is preferably of the O / W type, more preferably in the form of an O / W emulsion, and even more preferably in the form of an O / W gel emulsion.

[0196] O / W structures or constructions that contain an oil phase dispersed in an aqueous phase have an external aqueous phase and therefore products based on O / W structures or constructions are more pleasant to use due to the sensation of immediate freshness that they can provide.

[0197] [Cosmetic methods and uses] The composition according to the present invention may be intended to be used as a cosmetic composition. Thus, the cosmetic composition according to the present invention may be intended to be applied to keratinous materials. Keratinous materials herein mean materials that contain keratin as a main component, examples of which include skin, scalp, nails, lips, hair, etc. Thus, the cosmetic composition according to the present invention is preferably used in a cosmetic method for keratinous materials, particularly skin.

[0198] Thus, the cosmetic composition according to the present invention may be a skin cosmetic composition, preferably a skin care composition or a skin make-up composition.

[0199] The composition according to the invention can preferably be used as a leave-on or rinse-off cosmetic composition for keratinous materials such as skin. The term "leave-on" as used herein means that the composition according to the invention is not removed from the keratinous material after it has been applied onto the keratinous material. The term "rinse-off" as used herein means that the composition according to the invention is removed from the keratinous material by rinsing after it has been applied onto the keratinous material. Water can be used for rinsing. Even after rinsing off, the composition according to the invention can remain and form a film or coating on the keratinous material such as skin.

[0200] The present invention also relates to a cosmetic method for keratinous substrates, such as the skin, comprising the step of applying to the keratinous substrate a composition according to the present invention.

[0201] By cosmetic method is meant herein a non-therapeutic cosmetic method for caring for and / or making up the surfaces of keratinous substrates such as the skin.

[0202] Since the composition according to the present invention comprises (a) an inorganic UV filter and (b) an organic UV filter, the cosmetic method can protect keratinous substrates such as skin from ultraviolet rays, thereby reducing skin darkening, improving skin tone and evenness, and / or treating skin aging.

[0203] The present invention also provides To improve the smooth texture of the composition, In a composition comprising (a) at least one inorganic UV filter in an amount of more than 5% by weight relative to the total weight of the composition, It also relates to the use of (b) at least one organic UV filter selected from organosilicon compounds carrying at least one benzotriazole group.

[0204] The use according to the invention can reduce the squeaky sensation caused by a relatively large amount of (a) the inorganic UV filter in the composition.

[0205] The use according to the invention can result in an improved smooth texture during application of the composition to keratinous materials such as the skin.

[0206] The use according to the invention may also result in an improved smooth texture, even after rinsing the composition from keratinous materials such as the skin.

[0207] The explanations regarding components (a) to (d) of the composition according to the present invention are applicable to the explanations of the uses according to the present invention. EXAMPLES

[0208] The present invention will now be described in more detail by means of examples, which should not, however, be construed as limiting the scope of the present invention.

[0209] (Examples 1 to 6 and Comparative Examples 1 to 27) [Preparation] Each of the compositions according to Examples 1 to 6 and Comparative Examples 1 to 27 was prepared by mixing at room temperature (25° C.) the components shown in Tables 1 to 4. All numerical values ​​for the amounts of components in Tables 1 to 4 are based on the “mass %” of the raw materials.

[0210] [Table 1A]

[0211] [Table 1B]

[0212] [Table 2A]

[0213] [Table 2B]

[0214] [Table 3A]

[0215] [Table 3B]

[0216] [Table 4A]

[0217] [Table 4B]

[0218] [evaluation] (in vitro SPF) Each composition according to Examples 1 to 6 and Comparative Examples 1 to 27 was applied at 1.3 mg / cm 2 was applied onto a PMMA (polymethyl methacrylate) plate at 25° C. After each composition was dried, the UV absorption spectrum of the composition was measured with an SPF analyzer (UV-2000S), and the in vitro SPF value was calculated based on the UVB absorption intensity measured by the SPF analyzer.

[0219] The results are shown in Tables 1 to 4.

[0220] (PPD in vitro) Each composition according to Examples 1 to 6 and Comparative Examples 1 to 27 was applied at 1.3 mg / cm 2 was applied onto a PMMA (polymethyl methacrylate) plate at 25° C. After each composition was dried, the UV absorption spectrum of the composition was measured with an SPF analyzer (UV-2000S), and its in vitro PPD (prolonged immediate darkening) value was calculated by the UVA absorption / UVB absorption ratio based on the UVA absorption and UVB absorption measured by the SPF analyzer.

[0221] The results are shown in Tables 1 to 4.

[0222] (Smoothness during application) Each composition according to Examples 1 to 6 and Comparative Examples 1 to 27 was applied at 2 mg / cm 2 Each sample was applied to the underarms of three experts using their fingers. Panelists rated the smoothness during application on a scale of 1 (not very smooth = squeaky) to 5 (very smooth) and the scores were averaged.

[0223] The results are shown in Tables 1 to 4.

[0224] (Smoothness after rinsing) Each composition according to Examples 1 to 6 and Comparative Examples 1 to 27 was applied at 2 mg / cm 2 The composition was applied to the underarms of three experts using a finger in an amount of 100 ml. The panelists rated the smoothness after rinsing the composition off with tap water on a scale of 2 (not very smooth = squeaky) to 5 (very smooth) and the scores were averaged.

[0225] The results are shown in Tables 1 to 4.

[0226] (stability) After the compositions of Examples 1 to 6 and Comparative Examples 1 to 27 were prepared and stored at 4° C. for one month, each composition was observed under a microscope to confirm crystallization of the organic UV blocking agent.

[0227] Specifically, a small droplet of each of the compositions according to Examples 1 to 6 and Comparative Examples 1 to 27 was placed on a transparent glass plate, covered with a cover glass, and observed under a polarizing microscope (Olympus BX51).

[0228] If no crystals were observed, the result was rated as good.

[0229] If any crystals were observed it was rated as poor.

[0230] The results are shown in Tables 1 to 4.

[0231] (Summary) The compositions according to Examples 1 to 6 (a) can provide sufficient UV protection for both UVA and UVB, and a smooth feel both during application and after rinsing, even though they contain a relatively large amount of TiO2 as an inorganic UV filter.

[0232] Furthermore, the compositions according to Examples 1 to 6 are stable such that no crystals of (b) drometrizole trisiloxane as an organic UV screening agent are found therein.

[0233] The composition according to Comparative Example 1 does not contain drometrizole trisiloxane, therefore the UV protection provided by the composition is not sufficient and its smoothness is not good.

[0234] The composition according to Comparative Example 2 does not contain TiO2, and therefore the UV protection provided by the composition is not sufficient.

[0235] The composition according to Comparative Example 3 contains less than 5 wt. % TiO2, and therefore the UV protection provided by the composition is not sufficient.

[0236] The compositions according to Comparative Examples 4 to 27 do not contain drometrizole trisiloxane and therefore the smoothness during application or after rinsing is not good, or the UV protection (especially against UVA) provided by the compositions is not sufficient.

[0237] (Examples 7 to 11) [Preparation] Each of the compositions according to Examples 7-11 was prepared by mixing at room temperature (25° C.) the components shown in Table 5. All figures for the amounts of components in Table 5 are based on "mass %" of the ingredients.

[0238] [Table 5A]

[0239] [Table 5B]

[0240] [evaluation] (Emulsion stability) The compositions of Examples 7 to 11 were stored at 45° C. for 2 months after preparation, and then each composition was subjected to visual observation.

[0241] Specifically, 40 g of each of the compositions according to Examples 7 to 11 was filled into a transparent glass bottle and stored for 2 months at 45° C. The appearance of the transparent glass bottle was visually confirmed.

[0242] If no change was observed, it was rated as good.

[0243] If there was a slight color change or slight phase separation (eg, oil floating to the top), it was rated as acceptable.

[0244] If any color change or phase separation was observed it was rated as poor.

[0245] The results are shown in Table 5.

[0246] (Summary) The compositions according to Examples 7, 8 and 10 are more stable, whereas the compositions according to Examples 9 and 11, which do not contain isopropyl myristate or potassium cetyl phosphate, are less stable.

[0247] Thus, it is preferred that the composition comprising TiO2 and drometrizole trisiloxane also comprises (c) a fatty substance, such as isopropyl myristate, and / or (d) a phosphate compound, such as potassium cetyl phosphate.

Claims

1. (a) at least one inorganic UV filter; (b) at least one organic UV filter selected from organosilicon compounds having at least one benzotriazole group; A composition comprising: (a) A composition, wherein the amount of inorganic UV filters is greater than 5% by weight, relative to the total weight of the composition.

2. 2. The composition of claim 1, wherein the (a) inorganic UV filter is selected from titanium dioxide, zinc oxide, and mixtures thereof.

3. The composition according to claim 1, wherein the amount of (a) inorganic UV filter in the composition is 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.

4. (b) The organic UV screening agent is represented by the formula (1): About (3-a) / 2 Si(R 7 ) a -G (1) [In the formula, R 7 is optionally halogenated C 1 ~C 10 an alkyl group, a phenyl group, or a trimethylsilyloxy group; a is an integer ranging from 0 to 3, inclusive; G is directly bonded to the silicon atom and has the structural formula (2): 【Chemistry 1】 (In the formula, The Y groups may be the same or different and each may be C 1 ~C 8 Alkyl group, halogen atom, or C 1 ~C 4 an alkoxy group, provided that in the last case, two adjacent Y groups on the same aromatic ring may together form an alkylidene dioxy group, the alkylidene portion having 1 or 2 carbon atoms; X is O or NH; Z is hydrogen or C 1 ~C 4 is an alkyl group, n is an integer ranging from 0 to 3, inclusive; m is 0 or 1; p is an integer ranging from 1 to 10, inclusive is a monovalent group having the formula 2. The composition of claim 1, wherein the silane is selected from silanes and polyorganosiloxanes containing at least one structural unit having the formula:

5. (b) The organic UV filter is represented by the structural formulas (5) and (6): 【Chemistry 2】 [In the formula, R 7 The groups may be the same or different and each may be C 1 ~C 10 alkyl, phenyl, 3,3,3-trifluoropropyl, or trimethylsilyloxy group; R 7 At least 80% by number of groups are methyl groups; The D groups may be the same or different and each may be R 7 a group or a G group, r is an integer ranging from 0 to 50, inclusive; s is an integer ranging from 0 to 20, inclusive, with the proviso that when s=0, at least one of the two D groups is a G group; u is an integer ranging from 1 to 6, inclusive, and t is an integer ranging from 0 to 10, inclusive, with the proviso that t+u is 3 or greater; The G group is represented by the structural formula (2) 【Transformation 3】 (In the formula, The Y groups may be the same or different and each may be C 1 ~C 8 Alkyl group, halogen atom, or C 1 ~C 4 an alkoxy group, provided that in the last case, two adjacent Y groups on the same aromatic ring may together form an alkylidene dioxy group, the alkylidene portion having 1 or 2 carbon atoms; X is O or NH; Z is hydrogen or C 1 ~C 4 is an alkyl group, n is an integer ranging from 0 to 3, inclusive; m is 0 or 1; p is an integer ranging from 1 to 10, inclusive have] 2. The composition of claim 1, wherein the benzotriazole-substituted silicone compound is selected from the group consisting of:

6. (b) The organic UV screening agent has the structural formula (7): 【Chemistry 4】 wherein 0≦r≦10, 1≦s≦10, and E is a divalent group: 【Transformation 5】 is) 2. The composition of claim 1, wherein the benzotriazole-substituted silicone compound is selected from the group consisting of:

7. (b) the organic UV screening agent has the structural formula: 【Transformation 6】 2. The composition of claim 1, wherein the compound is drometrizole trisiloxane having the formula:

8. The composition according to claim 1, wherein the amount of the (b) organic UV filter in the composition is 1% by mass to 20% by mass, preferably 2% by mass to 15% by mass, and more preferably 3% by mass to 10% by mass, relative to the total mass of the composition.

9. The composition of claim 1 , wherein the composition further comprises (c) at least one fatty material.

10. 10. The composition according to claim 9, wherein the amount of (c) fatty substance in the composition is from 1% to 20% by weight, preferably from 3% to 15% by weight, more preferably from 5% to 10% by weight, relative to the total weight of the composition.

11. The composition of claim 1 , wherein the composition further comprises (d) at least one phosphate compound.

12. The composition according to claim 11, wherein the amount of (d) the phosphate compound in the composition is 0.01% by weight to 15% by weight, preferably 0.05% by weight to 10% by weight, and more preferably 0.1% by weight to 5% by weight, relative to the total weight of the composition.

13. The composition according to claim 1, which is a cosmetic composition, preferably a dermocosmetic composition, more preferably a skin care composition or a skin make-up composition.

14. A cosmetic method for keratinous substrates such as skin, comprising the step of applying to the keratinous substrate a composition according to any one of claims 1 to 13.

15. To improve the smooth texture of the composition, In a composition comprising (a) at least one inorganic UV filter in an amount greater than 5% by weight relative to the total weight of the composition, Use of (b) at least one organic UV filter selected from organosilicon compounds having at least one benzotriazole group.