Classifications

• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • 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

Definitions

• the invention relates to a new method for improving the stability of at least one derivative of, 3,5-triazine against UV radiation in the absence of any dibenzoylmethane derivative, consisting in associating with said derivative of 1, 3.5-triazine an effective amount of a compound chosen from the group consisting of:
• 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 of the skin. They promote the initiation of the erythematous reaction or amplify this reaction in certain subjects and may even be the origin gine of phototoxic or photoallergic reactions.
• UV-A rays have 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 of the skin. They promote the initiation of the erythematous reaction or amplify this reaction in certain subjects and may even be
• a new method for improving the stability of at least one 1,3,5-triazine derivative with respect to UV radiation in the absence of any dibenzoylmethane derivative, consisting in associating with said 1,3,5-triazine derivative above an effective effective amount of at least one compound chosen from the group consisting of: (a) compounds comprising at least one group of the following formula:
• compositions obtained in accordance with the process of the invention have the advantage of being particularly photostable, even after prolonged exposure to UV-A and UV-B radiation. These rays can be of natural (sun) or artificial (UV lamp) origin.
• - XL X 2 and X 3 identical or different, represent oxygen or a radical -NR-;
• the radicals R which are identical or different, denote hydrogen or a linear or branched C 1 -C 18 alkyl radical, a C 5 -C 12 cycloalkyl radical which may be substituted by one or more CC alkyl radicals;
• R 2 and R 3 are chosen from: hydrogen; a linear or branched C 1 -C 18 alkyl radical; a C 5 -C 12 cycloalkyl radical optionally substituted with one or more CC 4 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 (2), (3) or (4) below:
• R 4 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 4 -C 8 alkyl radical or a Cs-Cs cycloalkyl radical
• - B is chosen from: a linear or branched C- ⁇ -C 8 alkyl radical; a Cs-Cs cycloalkyl radical; an aryl radical optionally substituted by one or more C 1 -C 4 alkyl radicals;
• R 6 is hydrogen or a methyl radical
• a first preferred family of 1,3,5-triazine derivatives is that, in particular described in document EP-A-0517104 (the teachings of which are, as regards the very definition of these products, completely included as reference in the present description) of the 1,3,5-triazines corresponding to the formula (1) above and having all of the following characteristics:
• Xi, X 2 and X 3 are identical and represent oxygen - R 1 is chosen from: a C 5 -C 12 cycloalkyl radical optionally substituted with one or more dC 4 alkyl radicals; a radical of formula (2), (3) or (4) above in which:
• - B is a CC 4 alkyl radical
• - R 6 is the methyl radical
• R 2 and R 3 are chosen from: hydrogen; a linear or branched CrC ⁇ S alkyl radical; a C 5 -C 12 cycloalkyl radical optionally substituted by one or more CC alkyl radicals; a radical of formula (2), (3) or (4) above in which: - B is a CC 4 alkyl radical;
• R 6 is the methyl radical.
• a second preferred family of 1,3,5-triazine of the invention is that, disclosed in particular in EP-A-0570838 (whose teachings are, for matters relating to the definition of these products, entirely included for reference in the present description) of the 1,3,5-triazines corresponding to formula (1) and having all of the following characteristics:
• - Xi is oxygen
• X 2 is the radical -NH- or oxygen
• - X 3 is the radical -NH-; - R 3 is chosen from: a linear or branched C1-C18 alkyl radical; a C 5 -C 12 cycloalkyl radical optionally substituted with one or more C 1 -C 4 alkyl radicals;
• R is chosen from: hydrogen; an alkali metal; an ammonium radical; a radical of formula (4); a linear or branched CC 18 alkyl radical; a C 5 -C 12 cycloalkyl radical optionally substituted with one or more CC 4 alkyl radicals;
• R 2 is chosen from: a linear or branched C C ⁇ 8 alkyl radical; a C 5 -C 12 cycloalkyl radical optionally substituted with one or more C 4 -C 4 alkyl radicals;
• R 2 is chosen from hydrogen; a radical of formula (4); a linear or branched C C ⁇ 8 alkyl radical; a C 5 -C 12 cycloalkyl radical optionally substituted with one or more dC 4 alkyl radicals.
• a third preferred family of 1,3,5-triazine derivatives according to the invention is that, in particular described in document EP-A-0796851, the teachings of which are, as far as the very definition of these products is concerned, completely included. as reference in the present description) of the 1,3,5-triazines corresponding to the formula (1) and having all of the following characteristics:
• radicals R which are identical or different, denote hydrogen or a linear or branched C 1 -C 18 alkyl radical, a C 5 -C- ⁇ 2 cycloalkyl radical which may be substituted by one or more CC alkyl radicals 4 ;
• R 2 and R 3 identical or different, denote hydrogen or a radical R.
• a preferred 1,3,5-triazine is 2,4,6-tris [p- (2'-ethylhexyl-1'-oxycarbonyl) - anilino] -1,3,5-triazine which is a filter known per se , active in. UV-B, in solid form, and which is sold in particular under the trade name "UVINUL T150" by the company BASF.
• This product has the following formula
• R 'de notes a 2-ethylhexyl radical
• R 'de notes a 2-ethylhexyl radical and R denotes a tert-butyl radical.
• the derivative (s) of 1,3,5-triazine may be present in the compositions intended to be stabilized in accordance with the process of the invention, in contents generally ranging from 0.01% to 15% by weight, and preferably in contents ranging from 0.3% to 10% by weight, relative to the total weight of the composition.
• a first family of compounds in accordance with the invention comprise at least one group of formula (I)
• - Ar represents a phenyl residue optionally substituted with R 7 ;
• - G represents a hydrogen atom or a CC alkyl radical or a phenyl residue optionally substituted with R ' 7 ;
• - R 7 and R ' 7 are in meta or para position and are chosen from: hydrogen; a C ⁇ -C 8 alkoxy radical with a straight or branched chain; a straight or branched chain C 1 -C 8 alkyl radical or a group comprising at least one silicon atom; - D and E, identical or different, represent a COOR 8 residue or an R 9 residue; provided that at least one of the residues D or E is different from a hydrogen atom and that when G represents a hydrogen atom, at least one of the residues D or E represents a residue COOR 8 ; - R 8 represents a CC 8 alkyl radical with a straight or branched chain or a group comprising at least one silicon atom;
• R 9 represents a hydrogen atom or a -CN radical.
• ⁇ -cyano- ⁇ ⁇ '2-ethylhexyl diphenylacrylate or alternatively ethyl ⁇ -cyano- ⁇ , ⁇ '-diphenylacrylate.
• ⁇ -cyano- ⁇ , ⁇ '2-ethylhexyl diphenylacrylate also called octocrylene
• UVB ultraviolet absorbent
• ⁇ denotes a phenyl radical
• R- IO denotes the group CH 2 CH 2 C (CH 3 ) 2 and Ru denotes H
• R 10 denotes the group CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 and Ru denotes H
• R 10 denotes the group CH 2 CH 2 CH 2 CH 3 and Ru denotes OCH 3 in ortho from OR 10
• benzalmalonate derivatives such as those cited in patent applications EP-A-350 386 and more particularly the silicone silicones with benzalmalonate function as described in applications EP-A-0 392 882, EP-0 538 431, EP-A-0 709 080 and WO92 / 20690 (forming an integral part of the content of the description).
• the compounds of the 1-acrylonitrile-3-isoindolinone type are preferably chosen from those of structure (11) below:
• R 12 denotes a group chosen from CN, COORu, COR 14 and CONR 14 R 15
• R 13 denotes hydrogen, C r C 20 alkyl, C 2 -C alkenyl, 0 , C 3 -C 10 cycloalkyl or C cycloalkenyl 3 -C 10 , CrC 20 alkoxycarbonyl, CC 12 alkoxy, (CC 12 ) alkylamino, di- (CrC 12 ) alkylamino, the alkyl groups being optionally substituted by solubilizing groups chosen from carboxylate, sulfonate or ammonium groups ;
• R 14 and R 15 denote, independently of one another, hydrogen or a CC 8 alkyl radical.
• R 13 denotes hydrogen.
• R 12 denotes the group COOC 8 H ⁇ 7 and R 1 denotes hydrogen
• R 12 denotes the group COOCH 3 and R 13 denotes the hydrogen
• R 2 denotes the group CN and R 13 denotes hydrogen
• R 12 denotes the group COC 4 H 9 and R 13 denotes hydrogen
• R 12 denotes the group CONH 2 and R 3 denotes hydrogen.
• the compounds of the alkyl ⁇ , ⁇ '-diphenylbutadienicarboxylate type and those of the alkyl ⁇ -cyano- ⁇ , ⁇ 'diphenylbutadienecarboxylate type are preferably chosen from the compounds of structure (III) below: in which :
• R e and R 9 denote independently of each other hydrogen, C 1 -C 20 alkyl, C 3 -C 10 cycloalkyl, CC 20 alkoxycarbonyl, CC 12 alkoxy, (CC 2 ) alkylamino, di- (C ⁇ - C 12 ) alkylamino, the alkyl groups being optionally substituted by solubilizing groups chosen from carboxylate, sulfonate or ammonium groups;
• R 20 or R 2 ⁇ denote, independently of one another, C1-C 20 alkyl, cycloalkyl or bicyclo (C 7 -C ⁇ o) alkyl n and m denote, independently of one another, an integer from 1 to 3.
• R ⁇ 8 and R 19 denote hydrogen.
• Ris and R 19 denote simultaneously hydrogen, R 16 denotes CN and R 17 denotes the group CO 2 C 8 H 7 ;
• R 6 and R 17 simultaneously denote the group CO 2 C 2 H s .
• effective amount of photostabilizing agent according to the invention is meant an amount sufficient to obtain a notable and significant improvement in the photostability of the 1,3,5-triazine derivative (s) contained in the composition.
• the minimum quantity of photostabilizing agent to be used which can vary depending on the nature of the cosmetically acceptable support chosen for the composition, can be determined without any difficulty by means of a conventional test for measuring photostability.
• the photostabilizing compounds in accordance with the invention as described above are generally present in the compositions according to the invention at a content at least equal to 0.5% by weight, relative to the total weight of the composition. More preferably, this content ranges from 0.5% to 20% by weight, relative to the total weight of the composition.
• the sunscreen cosmetic compositions according to the invention can of course contain one or more complementary organic filters active in UVA and / or UVB (absorbers).
• additional filters can in particular be chosen from salicylic derivatives; camphor derivatives; triazine derivatives other than those mentioned above such as those described in patent applications EP-A-775698, EP-A-878469 and EP-A-933376; benzophenone derivatives; benzimidazole derivatives; bis-benzoazolyl derivatives as described in patents EP-A-0669323 and US 2,463,264; p-aminobenzoic acid derivatives; filter polymers and filter silicones such as those described in particular in application WO93 / 04665; micronized insoluble organic UV filters as described in applications WO95 / 22959, GB-A-2 303 549 and EP-A-893 119.
• complementary sunscreens active in UV-A and / or UV-B there may be mentioned: p-aminobenzoic acid, oxyethylenated p-aminobenzoate (25mol), 2-ethylhexyl p-dimethylaminobenzoate , ethyl p-aminobenzoate N-oxypropylenated glycerol p-aminobenzoate, homomenthyl salicylate, 2-ethylhexyl salicylate, triethanolamine salicylate, 4-isopropylbenzyl salicylate, menthyl anthranilate, l 2-phenyl benzimidazole 5-sulfonic acid and its salts, 3- (4'-trimethylammonium) -benzylidèn-bornan-2-on-methylsulfate, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone -5-sulfonate, 2,4
• polyorganosiloxanes with a benzotriazole function such as Dimetrizole Trisiloxane.
• 2,2'-methylene-bis- [6- (2H-benzotriazol-2-yl) -4- (methyl) phenol] sold under the name MIXXIM BB / 200 by the company FAIRMOUNT CHEMICAL.
• 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).
• artificial tanning and / or browning agents for the skin such as for example dihydroxyacetone (DHA).
• DHA dihydroxyacetone
• the cosmetic and / or dermatological 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 and 50 nm) of coated metal oxides or not, for example, nanopigments of titanium oxide (amorphous or crystallized in rutile form and / or anatase), iron, zinc, zirconium or cerium which are all well-known photoprotective agents acting by physical blocking ( reflection and / or diffusion) of UV radiation.
• Conventional coating agents are moreover alumina and / or aluminum stearate.
• Such coated or uncoated metal oxide nanopigments are in particular described in patent applications EP-A-0518772 and
• compositions in accordance with the present invention may also comprise conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic * or nonionic thickeners, softeners, antioxidants, free anti-radical agents, opacifiers, stabilizers , emolients, silicones, anti-foaming agents, perfumes, preservatives, surfactants, sequestrants, polymers, propellants, alkalizing or acidifying agents, or any other ingredient usually.
• cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic * or nonionic thickeners, softeners, antioxidants, free anti-radical agents, opacifiers, stabilizers , emolients, silicones, anti-foaming agents, perfumes, preservatives, surfactants, sequestrants, polymers, propellants, alkalizing or acidifying agents, or any other ingredient usually.
• the fatty substances can consist of an oil or a wax or their mixtures.
• oil is meant a compound which is liquid at room temperature.
• wax is intended to mean a compound which is solid or substantially solid at room temperature, and the melting point of which is generally greater than 35 ° C.
• oils mention may be made of mineral oils (petrolatum); vegetable (sweet almond oil, macadamia oil, blackcurrant seed, jojoba); synthetics such as perhydrosqualene, alcohols, fatty acids or esters (such as the benzoate of C ⁇ 2 -C ⁇ 5 alcohols sold under the trade name "Finsolv TN" by the company Finetex, octyl palmitate, lanolate d 'isopropyl, triglycerides including those of capric / caprylic acids), fatty esters and ethers oxyethylenated or oxypropylenated; silicone (cyclomethicone, polydimethysiloxanes or PDMS) or fluorinated, polyalkylenes.
• mineral oils petrolatum
• vegetable sweet almond oil, macadamia oil, blackcurrant seed, jojoba
• synthetics such as perhydrosqualene, alcohols, fatty acids or esters (such as the be
• waxy compounds there may be mentioned paraffin, carnauba wax, beeswax, hydrogenated castor oil.
• organic solvents mention may be made of lower alcohols and polyols.
• the thickeners can be chosen in particular from crosslinked polyacrylic acids, guar gums and modified or unmodified celluloses such as hydroxypropylated guar gum, methylhydroxyethylcellulose and hydroxypropylmethyl cellulose.
• compositions according to 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 oil-in-water or water-in-oil type.
• This composition may be in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / O or W / O / W) such as a cream, a milk, or in the form of a gel or a cream gel, of powder, of solid stick and optionally be packaged as an aerosol and be in the form of foam or spray.
• an emulsion simple or complex (O / W, W / O, O / W / O or W / O / W)
• a cream, a milk or in the form of a gel or a cream gel, of powder, of solid stick and optionally be packaged as an aerosol and be in the form of foam or spray.
• compositions according to the invention are in the form of an oil-in-water emulsion.
• the aqueous phase thereof may comprise a nonionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins. J. Mol. Biol. 13, 238 (1965), FR2 315 991 and FR 2 416 008).
• the cosmetic and / or dermatological 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 when used for the protection of the human epidermis against UV rays, or as an antisun composition, it may be in the form of a suspension or of dispersion in solvents or fatty substances, in the form of nonionic vesicular dispersion or alternatively 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, stick, aerosol or spray foam.
• the cosmetic composition according to the invention when used for protecting the hair, it can be in the form of shampoo, lotion, emulsion gel, nonionic vesicular dispersion, and can constitute, for example, a composition to be rinsed off, to apply before or after shampooing, before or after coloring or bleaching, before, during or after perm or def ⁇ sage, a styling or treating lotion or gel, a lotion or gel for brushing or setting, a composition of perm or straightening, coloring or bleaching of hair
• the composition when used as a makeup product for the eyelashes, the eyebrows, the nails or the skin, such as an epidermis treatment cream, foundation, lipstick stick, eyeshadow, blush, mascara or hgneur also called "eye liner", nail polish, it can be in solid or pasty, anhydrous or aqueous form, like oil in water or water in oil emulsions, nonionic vesicular dispersions or 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 entire formulation
• UVINUL T150 2,4,6-tris [p- (2'-ethylhexyl-1'-oxycarbonyl) -anilino] -1, 3,5-triazine ) residual after UV irradiation according to the following in vitro photostability test protocol:
• Films of solar formula are prepared by manual spreading of the product at a rate of 2 mg / cm 2 on a frosted polymethyl methacrylate (PMMA) support. UV irradiation of samples
• the samples are then exposed to the radiation of a HERAEUS Sun-test (source: Long arc Xenon 1.8 kW), in an enclosure whose temperature is regulated around 35 ° to 40 ° C, in order to simulate natural UV irradiation .
• HERAEUS Sun-test source: Long arc Xenon 1.8 kW
• This exposure corresponds to approximately 62 J / cm 2 UVA and 4.3 J / cm 2 UVB.
• UV filters After exposure, the UV filters are extracted in 50 g of ethanol per sample. The solutions obtained are analyzed by HPLC.
• the rate of residual filters after irradiation is given, for each of the filters of the formula, by the ratio of its concentration in the irradiated sample to its concentration in the non-irradiated sample.
• UVINUL N 539 clearly improves the photostability of Uvinul T 150 in combination.

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• 1998
  • 1998-11-10 FR FR9814156A patent/FR2785540B1/fr not_active Expired - Fee Related
• 1999
  • 1999-10-14 WO PCT/FR1999/002500 patent/WO2000027337A2/fr not_active Application Discontinuation
  • 1999-10-14 EP EP99947580A patent/EP1043966A1/de not_active Withdrawn
  • 1999-10-14 AU AU60974/99A patent/AU6097499A/en not_active Abandoned
  • 1999-10-14 JP JP2000580568A patent/JP2002529381A/ja not_active Withdrawn
  • 1999-11-08 AR ARP990105638A patent/AR021114A1/es not_active Application Discontinuation

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