Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4966—Triazines or their condensed derivatives

Definitions

• compositions for topical use, in particular intended for the photoprotection of the skin and / or lips and / or integuments against ultraviolet radiation (compositions hereinafter more simply called sunscreen compositions), as well as their uses in many cosmetic applications. More precisely still, it relates to compositions with improved photoprotective power comprising, in a cosmetically and / or dermatologically acceptable support: (i) at least one 1,3,5-triazine derivative as lipophilic organic sunscreen and (ii) at least one particular oil suitably selected, present in a determined quantity, and which is a triester of a benzene tricarboxylic acid.
• UV- B rays with wavelengths between 280 and 320 nm, known by the name UV- B, cause erythema and skin burns which can affect the development of natural tanning; this UV-B radiation must therefore be filtered.
• UV-A rays, with wavelengths between 320 and 400 nm, which cause browning of the skin are capable of inducing an alteration of the latter, in particular in the case of skin. sensitive or skin continuously exposed to solar radiation. UV-A rays cause in particular a loss of elasticity in the skin and the appearance of wrinkles, leading to premature aging.
• UV-A and / or UV-B are cosmetic compositions intended for photoprotection of the skin.
• sunscreen compositions are quite often in the form of an emulsion of the oil-in-water type (that is to say a cosmetically acceptable support consisting of an aqueous dispersing continuous phase and an oily dispersed discontinuous phase) which contains , at various concentrations, one or more conventional organic filters, lipophilic and / or hydrophilic, capable of selectively absorbing harmful UV radiation, these filters (and their quantities) being selected according to the sun protection factor sought, the factor of sun protection (SPF) expressed mathematically by the ratio of the dose of UV radiation necessary to reach the erythematogenic threshold with the UV filter with the dose of UV radiation necessary to reach the erythematogenic threshold without UV filter.
• SPF factor of sun protection
• the derivatives of 1, 3,5-triazine are particularly sought after in the cosmetic of the sun because they are highly active in UVB and even in UV-A for some of these compounds according to the nature of the substituents involved In addition, they are photostable, that is to say that they degrade little or not chemically under the action of UV radiation. They are described in particular in patent applications US 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469 and EP933376, and we know in particular:
• oils such as esters and more particularly of C12-C15 alkyl benzoates ("FINSOLV TN” from Finetex), or to triglycerides and in particular triglycerides of fatty acids 8-C12 (“MIGLYOL 812” from H ⁇ ls), or to monoalcohols or fatty polyols oxyethylenated or oxypropylenated (“CETIOL HE” from Henkel or "WITCONOL AM from WITCO).
• triazine derivatives confer, in the absence of other filters, a very limited photoprotective power to these supports and in addition the cosmetic properties which are attached to them are generally considered to be insufficient.
• the present invention aims to solve the above problems.
• oils of the triester type of benzoic triacid such as tridecyl trimellitate is well known for the formulation of many cosmetic products comprising a fatty phase. It is described in particular in application EP-A-0792637 relating to lipsticks. It is also mentioned in application EP-A-0194055 for the preparation of anhydrous cosmetic formulations without mineral oil.
• this type of oil constitutes the fatty phase of transparent microemulsions of the water-in-oil type with a low water content and necessarily containing as the sole emulsifier a specific phosphate ester.
• These microemulsions are used in particular as sunscreen products based on organic UV filters such as octyldimethyl para-aminobenzoate, octyl cinnamate, octyl salicylate or benzophenone-3 as well as self-tanning products.
• organic UV filters such as octyldimethyl para-aminobenzoate, octyl cinnamate, octyl salicylate or benzophenone-3 as well as self-tanning products.
• this type of oil is also used as an emollient in anhydrous solar products with a high degree of protection containing in a silicone oil the combination of two organic UV-B filters chosen from a cinnamate, a salicylate and a para-aminobenzoate and an organic UV-A filter of the benzophenone type.
• new cosmetic or dermatological compositions which are characterized by the fact that they comprise, in a cosmetically and / or dermatologically acceptable carrier, (i) at at least one UV filter of the type derived from 1,3,5-triazine, and (ii) at least one triester of a benzene tricarboxylic acid in an amount sufficient to solubilize all of said filter on its own.
• the present invention also relates to the use of such compositions in or for the manufacture of compositions intended for the protection of the skin and / or the lips and / or the integuments such as the hair, the eyelashes, the eyebrows or the nails. against ultraviolet radiation, especially solar radiation.
• Another finally object of the present invention lies in the use of at least one triester of a benzene tricarboxylic acid in or for the preparation of a cosmetic composition for protecting the skin and / or the lips and / or the integuments such as hair, eyelashes, eyebrows or nails against ultraviolet radiation, comprising a system for filtering UV radiation consisting of at least one derivative of 1,3,5-triazine, in order to improve the photoprotective power of said composition.
• - X 2 and X 3 identical or different, represent oxygen or the radical -NH-;
• R 2 and R 3 are chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted by one or more alkyl or hydroxyalkyl radicals; a linear or branched C-1-C- ⁇ s alkyl radical; a C 5 -C ⁇ 2 cycloalkyl radical optionally substituted by one or more C ⁇ -C alkyl radicals; a polyoxyethylenated radical comprising from 1 to 6 units of ethylene oxide and the terminal OH group of which is methylated; a radical of formula (II), (III) or (IV) below;
• - R is hydrogen or a methyl radical
• R 5 is a C 1 -C 9 alkyl radical
• - n is an integer ranging from 0 to 3;
• - m is an integer ranging from 1 to 10;
• - A is a C -Cs alkyl radical or a Cs-Cs cycloalkyl radical
• - B is chosen from: a linear or branched C- ⁇ -C alkyl radical a ; a C 5 -C 8 cycloalkyl radical; an aryl radical optionally substituted by one or more C 1 -C 4 alkyl radicals;
• a first more particularly preferred family of derivatives of 1, 3,5-triazine, in particular described in document EP-A-0 517 104, is that of the 1, 3,5-triazines corresponding to formula (I) above. and having all of the following characteristics: - X 2 and X 3 are identical and represent oxygen;
• - Ri is chosen from: a C 5 -C 2 cycloalkyl radical optionally substituted by one or more C 1 -C 4 alkyl radicals; a radical of formula (II), (III) or (IV) above in which:
• - B is a C1-C4 alkyl radical
• - R ⁇ is the methyl radical
• R 2 and R 3 are chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted by one or more alkyl or hydroxyalkyl radicals; a linear or branched C ⁇ -C ⁇ 8 alkyl radical; a Cs-C ⁇ 2 cycloalkyl radical optionally substituted by one or more CrC 4 alkyl radicals; a radical of formula (II), (III) or (IV) above in which:
• - B is a C 1 -C 4 alkyl radical
• a second preferred family of 1,3,5-triazine derivatives according to the invention is that of the 1,3,5-triazines corresponding to formula (I) and having all of the following characteristics:
• - X 3 is the radical -NH-; - R 3 is chosen from: a linear or branched C ⁇ -d 8 alkyl radical; a C 5 -C 2 cycloalkyl radical optionally substituted with one or more C 1 -C 4 alkyl radicals;
• - Ri is chosen from: hydrogen; an alkali metal; an ammonium radical; a radical of formula (IV); a linear or branched C- ⁇ -C ⁇ 8 alkyl radical; a C 5 -C 2 cycloalkyl radical optionally substituted with one or more C 1 -C 4 alkyl radicals;
• R 2 is chosen from: a linear or branched C ⁇ -C- alkyl radical
• a particularly preferred 1,3,5-triazine from this second family is 2 - [(p- (tertiobutylamido) anilino] -4,6-bis - [(p- (2'-ethylhexyl-1'-oxycarbonyl) anilino ] -1, 3,5- triazine or "Diethylhexyl Butamido Triazone" sold under the trade name "UVASORB HEB" by SIGMA 3Vet corresponds to the following formula: O
• R 'de notes a 2-ethylhexyl radical and R denotes a tert-radical. butyl.
• a third preferred family of compounds which can be used in the context of the present invention, and which is described in particular in document US Pat. No. 4,724,137, is that of the 1,3,5-triazines corresponding to formula (I) and having all of the characteristics following:
• R 2 and R 3 are identical and represent a C 6 -C 12 alkyl radical or a polyoxyethylenated radical comprising from 1 to 6 ethylene oxide units and the terminal OH group of which is methylated.
• a particularly preferred 1,3,5-triazine from this third family is 2,4,6- tris [p- (2'-ethylhexyl-1'-oxycarbonyl) anilino] -1, 3,5-triazine or "Ethylhexyl
• R 'de notes a 2-ethyl hexyl radical.
• the 1,3,5-triazine derivatives in accordance with the invention can also be chosen from bis-resorcinyl triazine derivatives of formula (V) below: in which :
• radicals R and R 8 identical or different, denote an alkyl radical in
• T 1 is a hydrogen atom or a C 1 -C 8 alkyl radical
• radicals R 7 and R 8 which may be identical or different, may also denote a residue of formula (1) below:
• - Rg denotes a covalent bond
• - pi is a number from 0 to 5;
• radicals R 10 , Ru and R- ⁇ 2 identical or different, denote an alkyl radical in C ⁇ -C- ⁇ 8 ; a C C 8 alkoxy radical or a residue of formula:
• R 13 where R 13 is a C 1 -C 5 alkyl radical
• R denotes a hydrogen atom, a C-rC-io alkyl radical, a radical of formula: - (CH 2 CHR 5 -O) n ⁇ Ri 5 where ni is a number from 1 to 16, R- ⁇ 6 is hydrogen or methylated or else a residue of structure -CH 2 -CH- (OH) -CH 2 ⁇ T ⁇ with Ti having the same meaning indicated above.
• R 15 denotes hydrogen, a metal cation M, a C1-C5 alkyl radical or a residue of formula - (CH 2 ) m 2 -OT ⁇ where m 2 is a number from 1 to 4 and Ti has the same meaning indicated below -above.
• - Qi is an alkyl radical in CrC- ⁇ 8 .
• the alkyl radicals are linear or branched and can be chosen, for example, from methylated, ethyl, n-propyl, isopropyl, n-butyl, sec.butyl, tert.butyl, amyl, isoamyl, tert.amyl, heptyl, octyl, isooctyl , nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl;
• the alkenyl radicals can be chosen, for example, from allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct- 2-enyl, n-dodec-2-enyl, iso-dodecenyl, n-octadec-4-enyl;
• the alkoxy radicals are linear or branched and can be chosen, for example, from methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec.-butoxy, tert.-butoxy, amyloxy, isoamyloxy or tert.amyloxy;
• - C1 or C 5 mono or dialkylamino radicals can be chosen, for example, from methylamino, ethylamino, propylamino, n-butylamino, sec.butylamino, tert.butylamino, pentylamino, dimethylamino, diethylamino, dibutylamino or methylethylamino.
• the metal cations are alkaline, alkaline-earth or metal cations chosen, for example, from lithium, potassium, sodium, calcium, magnesium, copper and zinc.
• the bis-resorcinyl triazine derivatives of formula (V) which can be used according to the invention are filters already known per se. They are described and prepared according to the summaries indicated in particular in patent application EP-A-0775698, the technical content of which is fully integrated into the present description.
• a compound derived from bis-resorcinyl triazine more particularly preferred in the context of the present invention is 2,4-bis ⁇ [4-2-ethyl-hexyloxy)] - 2-hydroxy] - phenyl ⁇ -6- (4- methoxy-phenyl) -1, 3,5-triazine or “Anisotriazine” sold under the trade name “TINOSORB S” by CIBA SPECIALTY CHEMICALS.
• the derivative (s) of 1,3,5-triazine are generally present in the compositions of the invention at a content which can range from 0.5% to 15%, preferably from 1% to 10% by weight, relative to the total weight of the composition.
• the triesters of a benzene tricarboxylic acid used in accordance with the present invention are generally chosen from triesters of a benzene tricarboxylic acid with linear or branched alcohols, saturated or unsaturated, having from 3 to 30 carbon atoms and preferably from 8 to 18 carbon atoms. They correspond to the following general formula (VI):
• hydrocarbon radical in a hydro radical 0 carbon atoms said hydrocarbon radical is preferably still still there.
• esters of trimellitic acid corresponding to the following general formula (VII):
• R 1 , R 2 , R 3 have the same meanings as those indicated for formula (VI) above, and are even more particularly chosen from:
• BISOFLEX TOT the commercial product sold under the name BISOFLEX TOT by the company International Specialty Chemical
• DUB TMl the commercial product sold under the name DUB TMl by the Company Stéarineries Dubois or under the name of ISOFOL ESTER 1293 by the Company Condisputeda
• Tricaprilyl / capryle trimellitate (R 1 , R 2 , R 3 identical or different denote caprilyl and / or capryle);
• Tridecyl trimellitate is particularly preferred for the practice of the present invention.
• the triesters of benzene tricarboxylic acids used in accordance with the present invention are generally present in the final compositions at contents ranging from 0.1 to 99% by weight relative to the total weight of said composition, and preferably at contents ranging from 0.5 to 50% by weight.
• the triester of a benzene tricarboxylic acid must be used in an amount such that it is sufficient to solubilize on its own all, or substantially all, of the filter derived from 1, 3,5-triazine present in the composition.
• This minimum quantity of solvent oil intended to ensure complete and stable dissolution of the solid filter can be conventionally determined from tests of the solubility of said filter in this solvent.
• the compositions in accordance with the invention can comprise, in addition to other complementary organic UV filters, active in UVA and / or UVB (absorbers), water-soluble or liposoluble, or even even insoluble in the cosmetic solvents commonly used in formulation.
• the additional organic UV filters are chosen in particular from anthranilates; cinnamic derivatives; salicylic derivatives, camphor derivatives; benzophenone derivatives; ⁇ , ⁇ '-diphenylacrylate derivatives, benzotriazole derivatives; benzalmalonate derivatives; benzimidazole derivatives; imadazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US2,463,264; p-aminobenzoic acid derivatives (PABA); derivatives of methylene bis- (hydroxyphenyl benzotriazole) as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; filter polymers and filter silicones such as those described in particular in application WO-93/04665; dimers derived from ⁇ -alkylstyrene such as those described in patent application DE19855649; 4,4-diarylbutadienes as described in patent applications
• UVINUL 400 Benzophenone-1 sold under the trade name "UVINUL 400" by BASF
• UVINUL D50 BASF - Benzophenone-3 or Oxybenzone
• UVINUL MS40 Benzophenone-4 sold under the trade name "UVINUL MS40" by BASF
• Benzotriazole derivatives - Drometrizole Trisiloxane sold under the name "S1LATRIZOLE” by RHODIA CHIMIE,
• Benzalmalonate derivatives - Benzalmalonate polyorganosiloxane sold under the trade name "PARSOL SLX" by HOFFMANN LA ROCHE and their mixtures.
• the more particularly preferred additional organic UV filters are chosen from the following compounds: - Ethylhexyl Salicylate,
• the cosmetic compositions according to the invention may also contain pigments or else nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of metal oxides coated or not as for example of titanium oxide nanopigments (amorphous or crystallized in rutile form and / or anatase), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se. Conventional coating agents are moreover alumina and / or aluminum stearate. Such metallic oxide nanopigments, coated or uncoated, are in particular described in patent applications EP-A-0518772 and EP-A-0518773.
• compositions according to the invention may also contain artificial tanning and / or browning agents for the skin (self-tanning agents), such as for example dihydroxyacetone (DHA).
• the compositions of the invention may also comprise conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents other than those used specifically in the context of the present invention, ionic or nonionic thickeners, softeners, antioxidants, anti-free radical agents, opacifiers, stabilizers, emollients, silicones, ⁇ -hydroxy acids, anti-foaming agents, hydrating agents, vitamins, insect repellents, perfumes, preservatives, surfactants, anti-inflammatories, substance P antagonists, fillers, polymers, propellants, basifying or acidifying agents, dyes or any other ingredient usually used in cosmetics, in particular for the manufacture of sunscreen compositions in the form of emulsions.
• conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents other than those used specifically in the context of the
• the fatty substances can be constituted by an oil or a wax or their mixtures, and they also include fatty acids, fatty alcohols and fatty acid esters.
• the oils can be chosen from animal, vegetable, mineral or synthetic oils and in particular from vaseline oil, paraffin oil, silicone oils, volatile or not, isoparaffins, polyolefins, fluorinated oils and perfluorinated.
• the waxes can be chosen from animal, fossil, vegetable, mineral or synthetic waxes known per se.
• compositions of the invention can be prepared according to techniques well known to those skilled in the art, in particular those intended for the preparation of emulsions of the oil-in-water or water-in-oil type.
• compositions can be presented in particular in the form of a simple or complex emulsion (O / W, W / O, O / W / O or W / O / W) such as a cream, a milk, a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
• a simple or complex emulsion O / W, W / O, O / W / O or W / O / W
• a cream gel such as a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of a foam or spray.
• the aqueous phase thereof may comprise a nonionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins. J. Mol. Biol. 13, 238 (1965), FR2315991 and FR2416008).
• the cosmetic composition of the invention can be used as a composition for protecting the human epidermis or the hair against ultraviolet rays, as a sunscreen composition or as a make-up product.
• the cosmetic composition according to the invention may be in the form of a suspension or of dispersion in solvents or fatty substances, in the form of nonionic vesicular dispersion or also in the form of an emulsion, preferably of the oil-in-water type, such as a cream or a milk, in the form of an ointment, gel, cream gel, solid stick, powder, stick, aerosol foam or spray.
• the cosmetic composition according to the invention when used for protecting the hair against UV rays, it can be in the form of a shampoo, lotion, gel, emulsion, nonionic vesicular dispersion and constitute, for example, a composition to rinse, apply before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, composition for perming or straightening, coloring or bleaching the hair.
• a shampoo, lotion, gel, emulsion, nonionic vesicular dispersion constitute, for example, a composition to rinse, apply before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, composition for perming or straightening, coloring or bleaching the hair.
• composition When the composition is used as an eyelash, eyebrow or skin makeup product, such as epidermis treatment cream, foundation, lipstick stick, eyeshadow, blush, mascara or liner also called “eyeliner", it can be in solid or pasty, anhydrous or aqueous form, such as oil in water or water in oil emulsions, nonionic vesicular dispersions or even suspensions.
• eyelash eyebrow or skin makeup product
• anhydrous or aqueous form such as oil in water or water in oil emulsions, nonionic vesicular dispersions or even suspensions.
• the aqueous phase (comprising in particular hydrophilic filters) generally represents from 50 to 95% by weight, preferably from 70 at 90% by weight, relative to the whole of the formulation
• the oily phase (comprising in particular the lipophilic filters) from 5 to 50% by weight, preferably from 10 to 30% by weight, relative to the whole of the formulation
• the (co) emulsifier (s) from 0.5 to 20% by weight, preferably from 2 to 10% by weight, relative to the whole of the formulation.
• an object of the invention is the use of a composition as defined above in or for the manufacture of a cosmetic or dermatological composition intended for the protection of the skin and / or the hair against ultraviolet radiation, especially solar radiation.
• Example 1 The solubilization time of 2,4-bis ⁇ [4-2-ethyl-hexyloxy)] - 2-hydroxy] -phenyl ⁇ -6- (4-methoxy-phenyl) -1, 3 was determined.
• 5-triazine (filter) in different solvents using the following test:
• Two sunscreen formulations were prepared (F1, according to the invention; F2, comparative) in the form of an oil-in-water type emulsion by varying the nature of the oil used.
• Each of these emulsions was produced by dissolving the filter in the fatty phase, then adding the emulsifier in this fatty phase brought to around 80 ° C., and finally by adding with rapid stirring the aqueous phase previously heated to this same temperature. .
• the sun protection factor (SPF) which was attached to them was then determined. This was determined using the in vitro 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 wavelength range from 290 to 400 nm and in calculating from them the sun protection factor according to a given mathematical equation. The results obtained were as follows:

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  • 2001-01-19 FR FR0100750A patent/FR2819717B1/fr not_active Expired - Fee Related
• 2002
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