MXPA99008495A - Cosmetic photoprotective compositions comprising a silicon derivative with a benzotriazol function and a benzoic triadium triester and its u - Google Patents
Cosmetic photoprotective compositions comprising a silicon derivative with a benzotriazol function and a benzoic triadium triester and its uInfo
- Publication number
- MXPA99008495A MXPA99008495A MXPA/A/1999/008495A MX9908495A MXPA99008495A MX PA99008495 A MXPA99008495 A MX PA99008495A MX 9908495 A MX9908495 A MX 9908495A MX PA99008495 A MXPA99008495 A MX PA99008495A
- Authority
- MX
- Mexico
- Prior art keywords
- composition according
- composition
- carbon atoms
- skin
- derivatives
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 98
- 239000002537 cosmetic Substances 0.000 title claims abstract description 27
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 230000003711 photoprotective Effects 0.000 title claims abstract description 13
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 11
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims abstract description 24
- 210000003491 Skin Anatomy 0.000 claims abstract description 23
- 210000000088 Lip Anatomy 0.000 claims abstract description 17
- 230000004224 protection Effects 0.000 claims abstract description 12
- 239000003921 oil Substances 0.000 claims description 39
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 27
- -1 trimethylsilyloxy Chemical group 0.000 claims description 21
- 229920001296 polysiloxane Polymers 0.000 claims description 16
- 150000003376 silicon Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000839 emulsion Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 4
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triurene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000111 anti-oxidant Effects 0.000 claims description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
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- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011701 zinc Substances 0.000 claims description 3
- DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor Chemical class C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N Dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 2
- 229940029983 VITAMINS Drugs 0.000 claims description 2
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003918 triazines Chemical class 0.000 claims description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
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- 238000005266 casting Methods 0.000 claims 2
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- 229940058287 Salicylic acid derivative anticestodals Drugs 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
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- 239000010703 silicon Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
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- 239000004698 Polyethylene (PE) Substances 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
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- NRTKYSGFUISGRQ-UHFFFAOYSA-N (3-heptanoyloxy-2,2-dimethylpropyl) heptanoate Chemical compound CCCCCCC(=O)OCC(C)(C)COC(=O)CCCCCC NRTKYSGFUISGRQ-UHFFFAOYSA-N 0.000 description 1
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
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- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- RTGQGAXEHFZMBG-UHFFFAOYSA-N 2-(2-nonanoyloxyethoxy)ethyl nonanoate Chemical compound CCCCCCCCC(=O)OCCOCCOC(=O)CCCCCCCC RTGQGAXEHFZMBG-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000005474 octanoate group Chemical class 0.000 description 1
- VIKVSUVYUVJHOA-BUHFOSPRSA-N octyl (E)-3-phenylprop-2-enoate Chemical compound CCCCCCCCOC(=O)\C=C\C1=CC=CC=C1 VIKVSUVYUVJHOA-BUHFOSPRSA-N 0.000 description 1
- PVRKSMXQZDJYKL-UHFFFAOYSA-N octyl 18-hydroxyoctadecanoate Chemical compound CCCCCCCCOC(=O)CCCCCCCCCCCCCCCCCO PVRKSMXQZDJYKL-UHFFFAOYSA-N 0.000 description 1
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 230000003287 optical Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 231100000760 phototoxic Toxicity 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 231100000075 skin burn Toxicity 0.000 description 1
- 230000003381 solubilizing Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- COXJMKGEQAWXNP-UHFFFAOYSA-N tris(14-methylpentadecyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCCCC(C)C)CC(=O)OCCCCCCCCCCCCCC(C)C COXJMKGEQAWXNP-UHFFFAOYSA-N 0.000 description 1
- FJFYFBRNDHRTHL-UHFFFAOYSA-N tris(8-methylnonyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C(C(=O)OCCCCCCCC(C)C)=C1 FJFYFBRNDHRTHL-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon(0) Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Abstract
The present invention relates to novel cosmetic compositions for topical use, in particular for the photoprotection of the skin and / or of the hair, which has an improved photoprotective power, and which are characterized in that they comprise, in a cosmetically acceptable support: (i) ) at least one silicon derivative with benzotriazole function as a lipophilic organic solar filter and (ii) at least one triester of the benzoic triacid, in an amount sufficient to solubilize the entire filter therein. Application to the protection of the skin, lips, hair, eyelashes, eyebrows, and nails against the effects of ultraviolet radiation
Description
COSMETIC COMPOSITIONS COMPRISING A DERIVATIVE
OF SILICON WITH A BENZOTRIAZOL FUNCTION AND A TRIESTER
OF BENZOIC TRIACIDO AND ITS USES
DESCRIPTION OF THE INVENTION
The present invention relates to novel cosmetic compositions for topical use, particularly intended for the photoprotection of the skin and / or the lips and / or c-the appendage of the skin against ultraviolet radiation (compositions hereinafter referred to simply as compositions sunscreens), as well as its use in numerous cosmetic applications. More precisely, the present invention relates to compositions with improved photoprotective power, comprising, in a cosmetically acceptable support: (i) at least one silicon derivative with benzotriazole function as lipophilic organic solar filter and (ii) an oil It is known that light radiation of wavelengths comprised between 280 nm and 400 nm allows tanning of the human epidermis and that it is conveniently selected, present in a certain amount, and that it is a tri-ester of benzoic acid.
REF .: 30986 the rays of wavelengths comprised between 280 and 320 nm, known under the name of UV-B, cause erythemas and skin burns that can harm the development of natural tanning; this UV-B radiation must thus be filtered. It is also known that UV-A radiations, of wavelengths comprised between 320 and 400 nm, which cause tanning of the skin, are susceptible to induce an alteration thereof, particularly in the case of a sensitive skin or a skin continuously exposed to solar radiation. UV-A rays cause in particular a loss of elasticity of the skin and the appearance of wrinkles that lead to premature aging. They favor the initiation of the erythematous reaction or amplify this reaction in certain subjects and may themselves be the source of phototoxic or photoallergic reactions. It is thus desirable to also filter the UV-A radiation. Numerous cosmetic compositions intended for photoprotection (UV-A and / or UV-B) of the skin have been proposed at present. These sunscreen compositions contain, in various concentrations and according to the nature of the selected galenic form, one or more lipophilic and / or hydrophilic classical organic filters capable of selectively absorbing the harmful UV radiation, these filters (and their amounts) are selected according to the of the protection index sought (the protection index (IP) is expressed mathematically by the ratio of the irradiation time necessary to reach the erythematogenic threshold with the UV filter at the time necessary to reach the erythematogenic threshold without UV filter). It is known that lipophilic UV organic filters which are of particular interest in sunscreen cosmetics and which are highly active both in UV-A and UV-B have been described in EP-A-0392883; EP-A-0660701; EP-A-0708108; EP-A-0711778; EP-A-711779. These are silanes or polyorganosiloxanes with benzotriazole function. They present the particularity but also the disadvantage of being solid at room temperature. Therefore, its use in an antisun cosmetic composition involves certain restrictions at the level of its formulation and its application, particularly when it comes to finding solvents that allow to solubilize them correctly. In this respect, most often, oils are used as esters, and more particularly alkyl benzoates of 12 to 15 carbon atoms ("FINSOLV TN" from Fintex), or triglycerides and particularly acid triglycerides. fatty acids of 8 to 12 carbon atoms ("MIGLYOL 812" from Hüls), or even monoalcohols or polyols such as ethanol, as well as their mixtures. Although these products have solubilizing properties compared to the aforementioned filters, they have the disadvantage of not having any activity of their own in the field of filtration of UV radiation, both UV-A and UV-B. The present invention aims to solve the problems mentioned above. The use of tri-acid benzoic triester oils such as tridecyl trimellitate is well known for the formulation of numerous cosmetic products comprising a fatty phase. It is particularly described in the application EP-A-0792637 relating to lipstick for lips. It is also mentioned in the application EP-A-0194055 for the preparation of anhydrous cosmetic formulations without mineral oil. In US Pat. No. 4,940,577, this type of oil constitutes the fatty phase of transparent microemulsions of the water-in-oil type with a reduced water content and which necessarily contains a specific phosphate ester as the sole emulsifier. These microemulsions are used in particular as sunscreen products based on organic UV filters such as octyldimethyl para-aminobenzoate, octyl cinnamate, octyl salicylate or 3-benzophenone, as well as self-tanning products. In US Pat. No. 4,940,574, this type of oil is also used as an emollient in anhydrous solar products with a high degree of protection which contain in a silicone oil the combination of two organic UV-B filters selected from a cinnamate, a salicylate and a para-aminobenzoate and an organic UV-A filter of the benzophenone type. As a consequence of important investigations conducted in the domain of photoprotection mentioned above, the Applicant has now unexpectedly and surprisingly discovered that it is possible to substantially improve the photoprotective power of a lipophilic UV filter of the silicon-derived type with a benzotriazole function contained in the photoprotective cosmetic compositions associating this particular filter with a suitably selected specific oil, and which is a tri-ester of the benzoic triazide, this oil must be present in the compositions in an amount sufficient to solubilize in it only the whole filter. This discovery is the basis of the present invention. Thus, according to one of the objects of the present invention, novel cosmetic or dermatological compositions are proposed, which are essentially characterized in that they comprise, in a cosmetically acceptable support, (i) at least one lipophilic UV filter of the type a silicon derivative with a benzotriazole function; and (ii) at least one triester of the benzoic triazide, in an amount sufficient to solubilize the entire filter therein. The subject of the present invention is also the use of such compositions for the manufacture of compositions intended for the protection of the skin and / or of the lips and / or of the skin such as the hair, the eyelashes, the eyebrows, or the nails. against ultraviolet radiation, in particular solar radiation.
Another purpose of the present invention resides in the use of at least one triester of the benzoic triazide in the preparation of a cosmetic composition for the protection of the skin and / or of the lips and / or of the facets such as hair, hair eyelashes, eyebrows or nails against ultraviolet radiation, comprising a system that filters UV radiation consisting of at least one silicon derivative with a benzotriazole function, in order to improve the photoprotective power of the composition. Other features, aspects and advantages of the present invention will appear on reading the detailed description that follows. The silicon derivatives with benzotriazole function used in the present invention are preferably silanes or siloxanes with a benzotriazole function comprising at least one unit of formula (1) below:
0 (3-a) / 2YES (R?) A-G (1
in which - R; represents an alkyl radical of 1 to 10 carbon atoms, optionally halogenated or a phenyl radical or a trimethylsilyloxy radical, a is an integer selected from 0 to 3, inclusive, and the symbol G designates a monovalent radical attached directly to an atom of silicon, and which answers the following formula (2):
in which: - And, identical or different, are selected from alkyl radicals of 1 to 8 carbon atoms, halogens and alkoxy radicals of 1 to 4 carbon atoms, it being understood that, in the latter case, two Y adjacent ones of the same aromatic nucleus can together form an alkylenedioxy group in which the alkylidene group contains 1 to 2 carbon atoms, X represents 0 or NH, Z represents hydrogen or an alkyl radical of 1 to 4 carbon atoms, n is an integer between 0 and 3. inclusive, - m is O or l, p represents an integer between 1 and 10, inclusive. These compounds are particularly described in patent applications EP-A-0392883; EP-A-0660701; EP-A-0708108; EP-A-0711778; EP-A-711779. Preferably, the silicon derivatives used in the context of the present invention belong to the general family of the benzotriazole silicones which is particularly described in
EP-A-0660701. A family of benzotriazole silicones which are particularly suitable for carrying out the present invention is that which groups together the compounds which correspond to the following formulas (3) or (4):
2 D-Si - O- Si- -Si- -Si- D (3) I R -i R-o
wherein: the radicals R 2, identical or different, are selected from the alkyl radicals of 1 to 10 carbon atoms, phenyl, trifluoro-3, 3, 3-propyl and trimethylsilyloxy, at least
80% by number of the radicals R 2 is methyl, -D, identical or different are selected from radicals R 2 and radical G, r is an integer from
0 and 50 inclusive, and s is an integer between 0 and 20, inclusive, and if s = 0, at least one of the two symbols D designates G, u is an integer between
1 and 6, inclusive, and t is an integer between 0 and 10 / inclusive, it being understood that t + u is equal to or greater than 3, and the symbol G corresponds to the formula (2) mentioned above.
As is emphasized from formula (2) given above, the union of the chain - (X) m- (CH2) p-CH (Z) -CH2- on the benzotriazole group, which thus ensures the connection of the benzotriazole group to the atom of the silicon chain can, according to the present invention, be made in all available positions offered by the two aromatic nuclei of benzotriazole:
Preferably, this connection is made in the 3, 4, 5 position (aromatic nucleus bearing the hydroxy function) or 4 '(benzene nucleus adjacent to the triazole ring), and still more preferably in the 3, 4 or 5 position. In a preferred embodiment of the invention, the connection is made in the 3-position. Likewise, the binding of or of the substituent groups Y can be done in all other positions available in the benzotriazole. Nevertheless, preferably this connection is made in positions 3, 4, 4 ', 5 and / or 6. In a preferred embodiment of the invention, the union of the group Y is done in position 5. In the formulas (3 ) and (4) mentioned above, the alkyl radicals can be linear or branched, and selected in particular from the group of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl radicals , neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl and tert-octyl. The preferred alkyl radicals R 2 according to the invention are methyl, ethyl, propyl, n-butyl, n-octyl and 2-ethylhexyl radicals. Still more preferably, the radicals R 2 are all methyl radicals. Among the compounds of formulas (3) or (4) mentioned above, it is preferred to apply those which correspond to formula (3), ie linear short-chain diorganosiloxanes. Among the compounds of formula (3) mentioned above, it is preferred to apply those for which the radicals D are both radicals R2. Among the linear diorganosiloxanes that fall within the scope of the present invention, the statistical derivatives or block-defined derivatives having at least one, and still more preferably all of the following characteristics, are more particularly preferred: D is a radical R2-R2 is alkyl or even more preferably is methyl, r is comprised between 0 and 15 inclusive; s is between 1 and 10 inclusive,
- n is not null, and preferably equal to 1, and Y is then selected from methyl, terbutyl or alkoxy of 1 to 4 carbon atoms, Z is hydrogen or methyl, m = 0, or [= 1 and X = O ] - p is equal to 1. A family of benzotriazole silicones which is particularly suitable for the invention is that defined by the following general formula (5):
with 0 < r < _ 1 0, 1 < s < 10, and where E represents the divalent radical:
-CHj-CH-CH2- CH3
In a particularly preferred embodiment of the invention, the benzotriazole silicone is the compound (called the compound
(a) in the following text) that responds to the following formula:
compound
The processes that suit the preparation of the aforementioned formula (1), (3), (4) and (5) products are particularly described in U.S. Patent Nos. 3,220,972, US 3,697,473, US 4,340,709, US 4,316,033, US 4,328,346 and in patent applications EP-A-0 392 883 and EP-A-0 742 003. Filters derived from silicon with benzotriazole function can be present in the compositions according to the invention in concentrations ranging from 0.1 to 20%, preferably ranging from 0.2 to 15%, by weight, always in relation to the total weight of the composition. According to an essential characteristic of the present invention, these compositions, taken alone or in mixtures, must be presented in. the final composition under a form totally, or substantially in a total form, solubilized. The tri-acid benzoic triesters used in accordance with the present invention are generally selected from tri-acid benzoic triesters with linear or branched, saturated or unsaturated alcohols having from 3 to 30 carbon atoms and preferably from 8 to 18 carbon atoms . They respond to the following general formula (I):
wherein R designates a linear or branched, saturated or unsaturated alkyl group, having from 3 to 30 carbon atoms, and preferably from 8 to 18 carbon atoms.
They are more preferably selected from the esters of trimellitic acid which corresponds to the following general formula (II):
wherein R has the same meaning indicated in formula (I) and more particularly between: 2-ethylhexyl trimellitate such as the commercial product sold under the name BISOFLEX TOT by the International Chemical Specialty Society; decyl trimellitate; triisodecyl trimellitate such as the commercial product sold under the name DUB TMI by the company STEARINERIES DUBOIS; - 2-butylhexyl trimellitate such as the commercial product sold under the name D 'ISOFOL ESTER 1293 by the Company CONDEA; tridecyl trimellitate such as the commercial product sold under the name LIPONATE TDTM by the LIPO CHEMICALS Company; or its mixtures.
This specific oil used according to the present invention is generally present in the final compositions in concentrations ranging from 0.1 to 99% by weight relative to the total weight of the composition, and preferably in concentrations ranging from 0.5 to 50% by weight. weight. According to an essential feature of the compositions according to the invention, the trisicide benzoic triester must be used in an amount such that it is sufficient to solubilize in it only all, or substantially all, of the silane or silicone filter with benzotriazole function present in the composition. This minimum amount of solvent oil intended to ensure a complete and stable dissolution of the solid filter can be determined in a conventional manner from filter solubility tests in this solvent. In a general manner, it will be noted that the filter and oil concentrations are selected such that the sunscreen index of the final composition is preferably at least 2. The applications of the triazide benzoic triester / filter combination UV of the type derived from silicon with benzotriazole function according to the invention are multiple, and are related to the set of cosmetic and dermatological products. The cosmetic or dermatological products of the invention may be in the form of solid, pasty or liquid, anhydrous or emulsion compositions. Thus, the composition of the invention can be presented under all galenic forms normally used for a topical application, and particularly in the form of an oil; of a suspension; of a two-phase product, of a dispersion of oil in water or water in oil; of a simple or complex emulsion (oil in water, water in oil, water in oil in water or oil in water in oil) such as a cream, a liquid cream, a gel-cream, an ointment, an ointment; a vesicular dispersion; a powder; a cast or molded solid such as a bar or a compacted product; a mousse or a spray. The compositions according to the invention can advantageously be used for the makeup and / or the care of the skin, both of the face and of the human body, of the lips and of the dusters such as the hair, the eyelashes, the eyebrows, the nails according to the nature of the active agents used. In particular, the compositions of the invention can be a carmine pencil for lips, a lip gloss (gloss in Anglo-Saxon terminology) usable as is or to be applied on a carmine lip film, particularly to increase its gloss (top coat in Anglo-Saxon terminology). They can also constitute a fluid or solid dye background, an anti-dark-skin or eye-contour product, a eyeliner, a mascara, a blush or an eye shadow, a nail varnish, a free powder, a body makeup product or even a product of care or cleaning of the skin, such as gel products. These compositions may also contain cosmetic or dermatological active agents, with the particular object of providing an aspect of care or treatment to the composition. More specifically, the invention relates to a lip product containing at least the combination as defined above. The compositions of the invention may further comprise conventional cosmetic adjuvants, particularly selected from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants and particularly ARL antioxidants, opacifiers, stabilizers, emollients. , silicones, fluorinated compounds, a-hydroxy acids, anti-foaming agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, pigments, nacres, fillers, sequestrants, polymers, the propellants, the alkalizing or acidifying agents, the dyes or any other ingredient commonly used in cosmetics. By pigments, it is to be understood the white or colored particles, mineral or organic, insoluble in the liquid fatty phase, intended to color and / or opacify the composition. By fillers, it is to be understood the colorless or white, mineral or synthetic particles, laminar or non-laminar. By nacres, it is going to understand the iridescent particles, particularly produced by certain molluscs in its shell or synthesized. These fillers and nacres serve in particular to modify the texture of the composition. As mineral pigments which can be used in the invention, mention may be made of titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides and ferric blue. Among the organic pigments which can be used in the invention, mention may be made of carbon black, and barium, strontium, calcium (red DC No. 7), aluminum lacquers.
Among the nacres which can be used in the invention, mention may be made of mica coated with titanium oxide, iron oxide, natural pigment or bismuth oxychloride, such as colored titanium mica. Particular mention may be made of talc, mica, kaolin, Nylon (particularly Orgasol) and polyethylene powders, Teflon, starch, boron nitride, copolymer microspheres such as Expancel (Nobel Industrie), polytrap (Dow Corning) and silicone resin microspheres (Tospearl from Toshiba, for example). The fatty substances that can be used in the compositions of the invention are generally selected according to the application considered between the oils, the waxes and the gums with their mixtures. The oils can be hydrocarbon and / or silicone and / or fluorinated oils. These oils can be of animal, vegetable, mineral or synthetic origin. By way of example of oil usable in the invention, mention may be made of hydrocarbon oils of animal origin, such as perhydrosqualene; vegetable or synthetic hydrocarbon oils such as triglycerides of fatty acids of 4 to 22 carbon atoms such as triglycerides of heptanoic or octanoic acids, triglycerides of hydrogenated coconut kernel, and triglycerides of caprylic / capric acids such as those sold by the company Stearineries Dubois, or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit; linear or branched hydrocarbons, of mineral or synthetic origin such as paraffin oils and their derivatives, petrolatum, polydecenes, hydrogenated polyisobutene such as parleam; esters and synthesis ethers, particularly of fatty acids such as oils of the formula R 3 COOR 4 in which R 3 represents the residue of a higher fatty acid comprising 7 to 29 carbon atoms, and R 4 represents a hydrocarbon chain containing 3 to 3 carbon atoms; at 30 carbon atoms, such as, for example, Purcellin oil, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, fatty alcohol heptanoates, octanoates, decanoates; polyol esters such as propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate; and the pentaerythritol esters; fatty alcohols having from 12 to 26 carbon atoms such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol; silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS), linear or cyclic, liquid or pasty at room temperature; and its mixtures. The waxes may be silicone and / or fluorinated hydrocarbons and be of vegetable, mineral, animal and / or synthetic origin. In particular, they have a melting temperature higher than 25 ° C, and better still higher than 45 ° C. As the wax to be used in the invention, mention may be made, lanolin with propylene oxide or not, acetylated or not, beeswax, Carnauba or Candelilla wax, paraffin, lignite or microcrystalline waxes, ceresin, or the ozokerite; synthetic waxes such as polyethylene waxes and Fischer-Tropsch waxes or even octacosanilestearate, silicone waxes such as alkyl or alkoxydimethicone having from 16 to 45 carbon atoms.
The nature and quantity of gums or waxes are a function of the mechanical properties and the textures sought. By way of indication, the composition may contain from 0 to 50% by weight of waxes, based on the total weight of the composition, and better than 5 to 30%. The cosmetic compositions according to the invention can be used as sunscreen products for the protection of the skin and / or hair against the harmful effects of UV radiation. The latter can occur in the form of suspension or dispersion in solvents or fatty substances, in the form of a non-ionic vesicular dispersion or even in the form of an emulsion, preferably of the oil-in-water type, such as a cream or a liquid cream, in the form of ointment, gel, cream gel, solid cylinder such as a bar, aerosol foam or aerosol. The compositions according to the invention can contain one or more complementary sunscreens active in the UVA and / or the UVB
(absorbent), hydrophilic or lipophilic, naturally different from the filter mentioned above.
These complementary filters can be selected in particular from cinnamic derivatives, salicylic derivatives, camphor derivatives, triazine derivatives, benzoquinone derivatives, dibenzoylmethane derivatives, ß-diphenyl-acrylate derivatives, p-aminobenzoic acid derivatives, the filter polymers and the silicone filters described in the application WO-93/04665. Other examples of organic filters are given in patent application EP-A 0 487 404. The compositions according to the invention can also contain tanning agents and / or artificial skin darkening agents (self-tanning agents), such as, for example, dihydroxyacetone. (DHA). The cosmetic compositions according to the invention can still contain nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 and 50 nm) of coated metal oxides, such as, for example, nanopigments of titanium oxide (amorphous or crystallized in the form of rutile and / or anatase), iron, zinc, zirconium or cerium, which are all well-known photoprotective agents, which act by physical blocking (reflection and / or diffusion) of UV radiation . The classic coating agents are on the other hand aluminum and / or aluminum stearate. Such nanopigments of metal oxides, coated or uncoated, are in particular described in the patent applications EP-A-0 518 772 and EP-A-0 518 773. The cosmetic compositions according to the invention can also be used for the protection of hair and can be presented in the form of shampoo, lotion, gel, emulsion, non-ionic vesicular dispersion, rinse composition, to apply before or after shampooing, before or after coloring or decoloration, before, during or after the permanent or neat, a lotion or a gel for combing or treating, a lotion or a gel for drying by hand or marking, a composition of permanent or straightening or coloring or discoloration of the hair. As indicated at the beginning of the description, another object of the present invention resides in a method of cosmetic treatment of the skin or of the hair intended to protect them against the effects of UV radiation, which consists in applying an effective amount thereof to them. a cosmetic composition such as defined above.
Now they are going to provide concrete examples, but not limiting, that illustrate the invention.
EXAMPLES 1 TO 6: Various antisun formulations were prepared which were presented in the form of an anhydrous solution containing: Benzotriazole silicone corresponding to compound (a) 5% by weight Oil 95% by weight The nature of the oil used was varied . The UV absorption spectrum between 280 and 400 nm was measured for each of the solutions in a Visible UV spectrophotometer: MODELO 552 from PERKIN-ELMER provided with a double beam and a UV lamp
(Deuterium) and a visible lamp (Bromide of
Tungsten). The device was equipped with an internal integration sphere of the PERKIN-ELMER house. Each of the undiluted solutions was exposed between two quartz sheets, of which one is hollow, to obtain a thickness of 10 μm. The optical density was determined in each of the spectra obtained at the wavelengths corresponding to the maximum absorption that are specific to the silicone filter with benzotriazole function used, namely:? Lmax. = 305 and? 2ma ?. = 347 nm. The results are indicated in Table A below:
Table A
These results clearly demonstrate in relation to the oils of the prior art, that the presence of the tridecyl trimellitate substantially increases the absorption power of the UV radiation of the benzotriazole silicone used as a UV filter and dissolved in the oil.
EXAMPLES 7 TO 10: Lip Care Bars Three formulations were prepared in the form of bars for lip care, whose composition was as follows:
Benzotriazole silicone corresponding to compound (a) 5% by weight Octacosanil stearate (Wax) sold under the name KESTER WAX 82 H by the company KOSTER KEUNEN 10% by weight Oil 85% by weight
The nature of the oil used was varied. For each of the formulations prepared in this manner, the sun protection factor (SPF) that was related to it was then determined. This was determined using the in vi tro method described by B.L. DIFFEY et al., In J. Soc. Cosmet. Chem. 40-127-133 (1989); this method consists in determining the monochromatic protection factors every 5 nm in a range of wavelengths from 290 to 400 nm, and in calculating from them the sun protection factor according to a given mathematical equation. For each of the bars, the measurements were made with the help of a visible UV spectrophotometer - model SPF 290 S from the OPTOMETRICS house - equipped with a UV lamp (Xenon) and an integration sphere. Each of the compositions was applied, in the form of a homogeneous deposit at a rate of 2 mg / cm2, on a TRANSPORE adhesive tape of the 3M house adhered on a quartz sheet. The compositions of the different formulations studied and their results in the average protection factor obtained are shown in Table B given below.
Table B
These results clearly demonstrate, in relation to the oils of the prior art, the remarkable beneficial effect brought about by the presence of the tridecyl trimellitate according to the invention at the level of the sun protection factors of the final compositions. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Claims (25)
1. Cosmetic or dermatological composition, characterized in that it comprises, in a cosmetically acceptable support: (i) at least one silicon derivative with a benzotriazole function as a lipophilic organic solar filter and; (ii) at least one tri-benzene triester and a sufficient amount to solubilize the entire filter therein.
2. Composition according to claim 1, characterized in that the silicon derivative with benzotriazole function is selected from silanes and / or polyorganosiloxanes with benzotriazole function comprising at least one unit of formula (1) below: wherein: R: represents an alkyl radical of 1 to 10 carbon atoms, optionally halogenated or a phenyl radical or a trimethylsilyloxy radical, a is an integer selected from 0 to 3 inclusive, and the symbol G designates a monovalent radical attached directly to a silicon atom, and which answers the following formula (2): wherein: and, identical or different, are selected from alkyl radicals of 1 to 8 carbon atoms, halogens and alkoxy radicals of 1 to 4 carbon atoms, it being understood that, in the latter case, two adjacent Ys of a same aromatic nucleus can together form an alkylenedioxy group in which the alkylidene group contains 1 to 2 carbon atoms, X represents O or NH, Z represents hydrogen or an alkyl radical of 1 to 4 carbon atoms, n is a number integer comprised between 0 and 3. inclusive, m is 0 or 1, p represents an integer between 1 and 10, inclusive.
3. Composition according to claim 1 or 2, characterized in that the silicon derivative with benzotriazole function corresponds to one of the following formulas (3) or (4): in which: - the radicals R 2, identical or different, are selected from alkyl radicals of 1 to 10 carbon atoms, phenyl, trifluoro-3, 3, 3-prspilo and trimethylsilyloxy, at least 80% by number of radicals R2 is methyl, D, identical or different are selected from radicals R2 and radical G, r is an integer between 0 and 50, inclusive, and s is an integer between 0 and 20 inclusive, and if s = 0 , at least one of the two symbols D designates G, u is an integer between l and ß. inclusive, and t is an integer between 0 and 10 inclusive, it being understood that t + u is equal to or greater than 3, and the symbol G corresponds to the formula (2) defined in claim 2.9.
4. Composition according to claim 3, characterized in that the silicon derivative with benzotriazole function corresponds to the following formula (5): with 0 < r < 10, 1 < s < 10 and where E represents the divalent radical: -CH, -CH-CH2- 2 I 2 CH,
5. Composition according to claim 4, characterized in that the silicon derivative with benzotriazole function corresponds to the following formula:
6. Composition according to any of claims 1 to 5, characterized in that the silicon derivatives with benzotriazole function are present in a concentration ranging from 0.1% to 20%, preferably from 0.2% to 15% by weight, based on weight total of the composition.
7. Composition according to any of claims 1 to 5, characterized in that the triesters of the benzoic triacid are selected from among those corresponding to the following general formula (I): wherein R designates a linear or branched, saturated or unsaturated alkyl group, having from 3 to 30 carbon atoms, and preferably from 8 to 18 carbon atoms.
8. Composition according to claim 7, characterized in that the triesters of the benzoic triacid are selected from the triesters of trimellitic acid which correspond to the following general formula (II): in which R has the same meaning indicated in formula (I).
9. Composition according to claim 8, characterized in that the compound of formula (II) is selected from: 2-ethylhexyl trimellitate; decyl trimellitate; - triisodecyl trimellitate; 2-butylhexyl trimellitate; tridecyl trimellitate; or its mixtures.
10. Composition according to any one of claims 1 to 9, characterized in that the triazide benzoic triester is present in concentrations ranging from 0.1 to 99% by weight with respect to the total weight of the composition, and preferably in concentrations ranging from 0.5. to 50% by weight.
11. Composition according to any one of claims 1 to 10, characterized in that the concentration of the silicon derivative with benzotriazole function and triazide benzoic triester compound are selected in such a way that the sun protection index of the composition is preferably less 2
12. Composition according to any of claims 1 to 11, characterized in that it is presented in the form of a solid, pasty or liquid, anhydrous or emulsion composition.
13. Composition according to any of claims 1 to 12, characterized in that it is presented in the form of an oil; of a gel; of a suspension; of a two-phase product, a dispersion of oil in water or water in oil; of a simple or complex emulsion; of a vascular dispersion; of a solid casting or casting; of a powder; of a foam or a spray.
14. Composition according to any of claims 1 to 13, characterized in that it is a makeup product and / or for the care of the skin and / or of the lips and / or of the face.
15. Composition according to claim 14, characterized in that it is in the form of a lip product.
16. Composition according to any of claims 1 to 15, characterized in that it contains, in addition to the cosmetic adjuvants selected among the fatty substances, the organic solvents, the ionic or nonionic thickeners, the softeners, the antioxidants and particularly the antioxidants. ARL, opacifiers, stabilizers, emollients, silicones, fluorinated compounds, a-hydroxy acids, anti-foam agents, moisturizing agents, vitamins, perfumes, preservatives, surfactants, pigments, nacres , fillers, sequestrants, polymers, propellants, alkalizing or acidifying agents and dyes.
17. Composition according to any of claims 1 to 16, characterized in that it is an antisun product for the photoprotection of the skin, of the lips and / or of the fañaras.
18. Composition according to any of claims 1 to 17, characterized in that it also comprises one or more complementary organic filters active in UV-A and / or UV-B, hydrophilic or lipophilic.
19. Composition according to claim 18, characterized in that the complementary organic filters are selected from among the camphor derivatives, the triazine derivatives, the cinnamic acid derivatives, the salicylic acid derivatives, the benzophenone derivatives, the dibenzoylmethane derivatives, the derivatives of ß, ß-diphenylacrylate, the p-aminobenzoic acid derivatives, the filter polymers and the silicone filters different from the silicon derivatives with benzotriazole function.
20. Composition according to any one of claims 1 to 19, characterized in that it also comprises, as complementary light stabilizers, pigments or nanopigments of metal oxides, coated or not, capable of physically blocking, by diffusion and / or reflection, UV radiation.
21. Composition according to claim 20, characterized in that the pigments or nanopigments are selected from among the oxides of titanium, zinc, iron, zirconium, cerium and their mixtures, whether coated or not.
22. Composition according to any of claims 1 to 21, characterized in that it also comprises at least one agent for tanning and / or artificial darkening of the skin.
23. Composition according to any of claims 1 to 19, characterized in that it is a capillary product.
24. The use of a composition as defined in claims 1 to 24, characterized in that it is for the manufacture of a cosmetic composition intended for the protection of the skin and / or of the lips and / or the skin against UV radiation.
25. The use of at least one triester of the benzoic triazide as defined in the preceding claims, characterized in that it is used in the manufacture of a cosmetic composition for the protection of the skin and / or of the lips and / or of the skin against the UV radiation, containing a system that filters lipophilic UV radiation, consisting of at least one silicon derivative with benzotriazole function, to improve the photoprotective power of the composition.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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FR9811946 | 1998-09-24 |
Publications (1)
Publication Number | Publication Date |
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MXPA99008495A true MXPA99008495A (en) | 2000-12-06 |
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