WO2022129039A1 - Composition cosmétique comprenant une mérocyanine, un filtre uv du type triazine et un polysaccharide modifié par des chaînes hydrophobes - Google Patents

Composition cosmétique comprenant une mérocyanine, un filtre uv du type triazine et un polysaccharide modifié par des chaînes hydrophobes Download PDF

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WO2022129039A1
WO2022129039A1 PCT/EP2021/085679 EP2021085679W WO2022129039A1 WO 2022129039 A1 WO2022129039 A1 WO 2022129039A1 EP 2021085679 W EP2021085679 W EP 2021085679W WO 2022129039 A1 WO2022129039 A1 WO 2022129039A1
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formula
radical
group
alkyl
composition according
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PCT/EP2021/085679
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Flavie GILLANT
Martin Josso
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L'oreal
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Priority to EP21824598.3A priority Critical patent/EP4262714A1/fr
Priority to MX2023007221A priority patent/MX2023007221A/es
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    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides

Definitions

  • the present invention relates to a composition, preferably a cosmetic or dermatological composition, comprising at least one merocyanine of formula (1 ) or (2) that will be defined below in detail, at least one triazine UV-screening agent, and at least one polysaccharide modified with hydrophobic chains.
  • the present invention also relates to the use of at least one such merocyanine of formula (1 ) or (2) for reducing the staining of fabrics, in particular of clothing, after washing.
  • UVA rays with wavelengths of between 320 and 400 nm penetrate more deeply into the skin than UVB rays. UVA rays cause immediate and persistent browning of the skin. Daily exposure to UVA rays, even of short duration, under normal conditions can result in damage to the collagen fibres and the elastin, which is reflected by a modification of the microrelief of the skin, the appearance of wrinkles and uneven pigmentation (liver spots, heterogeneity of the complexion).
  • UVA and UVB radiation Protection against UVA and UVB radiation is therefore necessary.
  • An effective photoprotective product must protect against both UVA and UVB radiation.
  • photoprotective compositions have been proposed to date to overcome the effects induced by UVA and/or UVB radiation. They generally contain organic UV-screening agents and/or inorganic UV-screening agents, which function according to their own chemical nature and according to their own properties by absorption, reflection or scattering of the UV radiation. They generally contain mixtures of liposoluble organic screening agents and/or of water-soluble UV-screening agents combined with metal oxide pigments such as titanium dioxide or zinc oxide.
  • compositions intended to limit darkening of the skin, and to improve the colour and uniformity of the complexion have been proposed to date. It is well known in the field of antisun products that such compositions can be obtained by using UV-screening agents, and in particular UVB- screening agents. Some compositions may also contain UVA-screening agents. This screening system must cover UVB protection for the purpose of limiting and controlling the neosynthesis of melanin promoting overall pigmentation, but must also cover UVA protection in order to limit and control the oxidation of the already existing melanin resulting in darkening of the skin colour.
  • compositions containing a particular combination of UV-screening agents that would be specially suitable for photoprotection of the skin and particularly for an improvement in the quality of the skin both in terms of the colour and in terms of its mechanical elasticity properties.
  • this improvement is particularly desired on skin that is already pigmented, for the purpose of increasing neither the pigmentary melanin load nor the structure of the melanin already present within the skin.
  • the majority of organic UV-screening agents consist of aromatic compounds which absorb in the wavelength range between 280 and 370 nm.
  • the desired photoprotective compounds must also have good cosmetic properties, good solubility in the usual solvents and in particular in fatty substances such as oils, and also good photostability alone or in combination with other UV-screening agents. They must also be colourless or at least have a colour that is cosmetically acceptable for consumers.
  • One of the main drawbacks known to date of these compositions is that these screening systems have insufficient efficiency against UV radiation and particularly against long UVA radiation with a wavelength above 370 nm with the aim of controlling light-induced pigmentation and the development thereof by means of a system which screens out UV radiation over the whole of the UV spectrum.
  • sunscreens and in particular those which protect against UVA rays, are well known to those skilled in the art, and leave yellow marks on clothing, these yellow marks being very difficult to remove during washing.
  • compositions notably cosmetic or dermatological composition, comprising at least one merocyanine of formula (1 ) or (2) that will be defined below in detail, at least one triazine UV-screening agent, and at least one polysaccharide modified with hydrophobic chains.
  • This composition makes it possible notably to obtain an anti-sun product which does not have the drawback of irreversibly staining clothing or other fabrics.
  • this composition has good cosmetic properties, and in particular it is fresh and light on application. Furthermore, it makes it possible to obtain a good level of photoprotection over broad-spectrum (UVA + UVB).
  • a subject of the present invention is also the use of at least one merocyanine of formula (1 ) or (2) that will be defined in detail below, for reducing the staining of fabrics, in particular clothing.
  • the present invention also relates to a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of said keratin material, of at least one composition according to the invention as defined above.
  • the present invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
  • the present invention also relates to a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
  • composition according to the invention is intended for topical application and thus contains a physiologically acceptable medium.
  • physiologically acceptable medium means here a medium that is compatible with keratin materials.
  • the term “keratin material” notably means the skin, the scalp, keratin fibres such as the eyelashes, the eyebrows, head hair, bodily hair, the nails, and mucous membranes such as the lips, and more particularly the skin and the mucous membranes (of the body, face, area around the eyes, eyelids, lips, preferably of the body, face or lips).
  • the term “preventing” or “prevention” is intended to mean reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of ageing of a keratin material.
  • organic UVA-screening agent is intended to mean any organic chemical molecule capable of absorbing at least UVA rays in the wavelength range of between 320 and 400 nm; it being possible for said molecules to likewise also absorb UVB rays in the wavelength range of between 280 and 320 nm.
  • organic UVB-screening agent is intended to mean any organic chemical molecule capable of absorbing exclusively UVB radiation in the wavelength range of between 280 and 320 nm.
  • the level of sun protection is defined by the sun protection factor (SPF), which is expressed mathematically as the ratio of the exposure time necessary to reach the erythema-forming threshold with the UV screening agent to the time necessary to reach the erythema-forming threshold without UV screening agent.
  • SPDF sun protection factor
  • composition in accordance with the invention comprises at least one UVA-screening agent of merocyanine type as defined below.
  • these merocyanine compounds correspond to formula (1 ) or (2) below:
  • Ri and R2 independently of each other, are hydrogen; a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, these groups possibly being substituted with at least one hydroxyl group or else interrupted with at least one -O-; or else Ri and R2 form, together with the nitrogen atom which links them, a -(CH2)n- ring which may be optionally interrupted with -0- or -NH-;
  • Re is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being substituted with one or more OH;
  • R4 and R5 are hydrogens; or R4 and R5 form a -(CH2)n- ring which may be substituted with a C1-C4 alkyl group and/or interrupted with one or more -O- or with -NH-; n is a number between 2 and 7;
  • R7 and Rs independently of one another, are hydrogen; a C1-C22 alkyl group, a C2- C22 alkenyl group, a C2-C22 alkynyl group, said groups possibly being interrupted with one or more 0 and/or substituted with one or more OH; a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more -O-; or else R7 and Re form, together with the nitrogen which links them, a -(CH2)n- ring which may be interrupted with one or more -O-;
  • R9 and R10 are hydrogen; or R9 and R10 form a -(CH2)n- ring potentially substituted with a C1-C4 alkyl and/or interrupted with an -0- or -NH-;
  • A is -O-; or -NH;
  • R11 is a C1-C22 alkyl group; a C2-C22 alkenyl group; a C2-C22 alkynyl group; a C3- C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more 0; or a C1-C22 alkyl group or a C2-C22 alkenyl group which is substituted with a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said C3-C22 cycloalkyl group or C3-C22 cycloalkenyl group possibly being interrupted with one or more -O-.
  • the compounds of formula (1 ) or (2) have the following characteristics:
  • Re is substituted with one or more OH, one from among R1 and R2 is a C4-C22 alkyl group; or else R1 and R2 form, together with the nitrogen to which they are bonded, a piperidyl or morpholinyl radical;
  • the preferred compounds are those of formula (1 ) or (2) in which:
  • R1 and R2 independently of each other, are hydrogen; a C4-C12 alkyl group; or a C3-C12 hydroxyalkyl group; or at least one of R1 or R2 is a C3-C12 hydroxyalkyl group; and
  • R3, R4 and R5 have the same meanings indicated previously.
  • Re is a C1-C12 alkyl group, which may be substituted with one or more hydroxyls.
  • Re is a C1-C12 alkyl group, which may be substituted with one or more hydroxyls; one of the R1 or R2 radicals is a C4-C22 alkyl group; or else R1 and R2 form, together with the nitrogen which links them, a -(CH2)n- ring which may be interrupted with - 0- and/or -NH-; and
  • R4 and R5 and n have the same meanings indicated previously.
  • R11 is a -(CH2)m-O-R-i2 radical, in which
  • R12 is a C1-C12 alkyl group; or a C-i-Ce alkoxy-C-i-Ce alkyl group; m is a number from 1 to 5; and
  • R7, Rs, R9, R10 and A have the same meanings indicated previously.
  • the compounds that are even more preferential are those of formula (1 ) or (2), in which: Ri and R2, on the one hand, and R7 and Rs, on the other hand, respectively form, together with the nitrogen atom to which they are respectively bonded, a piperidyl radical or a morpholinyl radical.
  • R4 and R5 and R9 and R10 respectively form a carbon-based ring which contains 6 carbon atoms.
  • R1 and R2 independently of each other, are a hydrogen; or a C1-C22 alkyl group; or a C1-C22 hydroxyalkyl group; or R1 and R2 form, together with the nitrogen to which they are bonded, a piperidyl or morpholinyl radical;
  • Re is a C1-C22 alkyl group, which may be substituted with one or more -OH;
  • R4 and R5 are a hydrogen; or R4 and R5 are linked together to form a carbon-based ring which contains 6 carbon atoms.
  • R1 and R2 independently of each other, are a hydrogen; or a C1-C22 hydroxyalkyl group; in which at least one of the R1 and R2 radicals is a C1-C22 hydroxyalkyl group;
  • Re is a C1-C22 alkyl group
  • R4 and R5 are hydrogens; or R4 and R5 are bonded together to form a carbonbased ring which contains 6 carbon atoms.
  • R7 and Rs independently of each other, are a hydrogen or a C-i-Ce alkyl group, which may be interrupted with one or more -O-;
  • A is -0- or -NH
  • R11 is a C1-C22 alkyl
  • R9 and R10 are a hydrogen; or R9 and R10 are bonded together to form a carbonbased ring which contains 6 carbon atoms.
  • the most preferential compounds are those of formula (2), in which:
  • R? and Rs form, together with the nitrogen atom to which they are bonded, a morpholinyl or piperidyl radical;
  • A is -0- or -NH
  • Ri 1 is a C1-C22 alkyl group, which may be interrupted with one or more -O-;
  • R9 and R10 are hydrogens; or R9 and R10 are bonded together to form a carbonbased ring which contains 6 carbon atoms.
  • R11 is a -(CH2)m-O-R-i2 radical, in which
  • R12 is a C1-C4 alkyl group; or a C1-C4 alkoxy-Ci-C4 alkyl group; m is a number from 1 to 3;
  • R7 and Rs independently of each other, are a hydrogen; a C1-C12 alkyl group, which may be interrupted with one or more 0; or R7 and Rs form, together with the nitrogen atom to which they are bonded, a morpholinyl or piperidyl radical;
  • R9 and R10 are hydrogens or together form a carbon-based ring which contains 6 carbon atoms
  • A is -0- or -NH.
  • the merocyanine compounds of the invention may be for example in the E/E-, E/Z- or Z/Z-geometric isomer form.
  • alkyl, cycloalkyl, alkenyl, alkylidene or cycloalkenyl chains may be linear or branched, monocyclic or polycyclic chains.
  • a C1-C22 alkyl group is, for example, a methyl, ethyl, n-propyl, isopropyl, n- butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2- dimethylpropyl, n-hexyl, n-octyl, 1 ,1 ,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, decyl, n-octadecyl, eicosyl or dodecyl.
  • a substituted alkyl group is, for example, a methoxyethyl, ethoxypropyl, 2- ethylhexyl, hydroxyethyl, chloropropyl, N,N-diethylaminopropyl, cyanoethyl, phenethyl, benzyl, p-tert-butylphenethyl, p-tert-octylphenoxyethyl, 3-[2,4- bis(tert-amyl)phenoxy]propyl, ethoxycarbonylmethyl-2-(2- hydroxyethoxy)ethyl or 2-fury lethy I .
  • a hydroxy-substituted alkyl group is, for example, a hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl or hydroxydecyl.
  • a C2-C22 alkenyl group is, for example, a linear C2-C12 alkenyl chain or preferentially a branched C3-C12 alkenyl chain.
  • a C2-C22 alkenyl is for example a vinyl, allyl, 2-propen-2-yl, 2-buten-1-yl, 3-buten-1-yl, 1 ,3-butadien-2-yl, 2- cyclobuten-1 -yl, 2-penten-1-yl, 3-penten-2-yl, 2-methyl-1-buten-3-yl, 2- methyl-3-buten-2-yl, 3-methyl-2-buten-1-yl, 1 ,4-pentadien-3-yl, 2- cyclopenten-1 -yl, 2-cyclohexen-1-yl, 3-cyclohexen-1 -yl, 2,4-cyclohexadien-1- yl, 1 -p-menthen-8-yl, 4(10)-thujen
  • a C3-C12 cycloalkyl group is, for example, a cyclopropyl, cyclobutyl, cyclopentyl or trimethylcyclohexyl or, preferentially, a cyclohexyl.
  • R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more 0.
  • the merocyanine compounds of the invention may be in the E/E- or E/Z- geometric isomer forms thereof;
  • the compounds of formula (3) that are even more preferential are those in which: A is -O-; R is a C1-C22 alkyl, which may be interrupted with one or more 0.
  • the E/E form has the following structure:
  • the screening merocyanines in accordance with the invention may be present in the compositions according to the invention in a concentration ranging from 0.1 % to 15% by weight, and preferentially from 0.2% to 10% by weight and even better still from 0.5% to 5% by weight relative to the total weight of the composition.
  • the compounds of formulae (1 ) and (2) and especially of formula (3) may be prepared according to known processes, as described, for example, in J. Org. Chem. USSR (English Translation) 26(8), p. 1562f (1990); J. Heterocycl. Chem. 33(3), p. 763-766 (1996); Khimiya Geterotsiklicheskikh Soedinenii 11 , p. 1537-1543 (1984); Khimiya Geterotsiklicheskikh Soedinenii 3, p. 397-404 (1982); Chem. Heterocycl. Comp. (English Translation) 24(8), 914-919 (1988) and in Synthetic Communications Vol. 33, No. 3, 2003, p 367- 371.
  • CH-acid vinylogen compounds are reacted with amide acetals.
  • the compounds of formula (1 ) or (2) in which R4 and R5, on the one hand, or R9 and R10, on the other hand, together form a carbocyclic ring containing 6 carbon atoms, respectively, may be prepared according to the protocols described in patent application WO 2007/071582, in IP.com Journal (2009), 9(5A), 29-30 IPCOM000182396D under the title “Process for producing 3- amino-2-cyclohexan-1-ylidene compounds” and in US-A-4,749,643 on col. 13, line 66 - col. 14, line 57 and the references cited in this regard.
  • the compounds of formula (3) such as compound 2-ethoxyethyl (2Z)-cyano ⁇ 3-[(3-methoxypropyl)amino]cyclohex-2-en-1 - ylidenejethanoate (25) can be synthesized according to the synthesis scheme described in the publication by B. Winkler et al., Tetrahedron Letters, 55 (2014) 1749-1751 , which is intitled « A cyclic merocyanine UV- A absorber : mechanism of formation and crystal structure » and shown below, for the compounds of formula (3) :
  • the composition comprises at least one triazine derivative chosen from the 1 ,3,5- triazine derivatives of formula (10) below:
  • - X a (each of the X a may be identical or different) represents oxygen or -NH-;
  • R a (each of the R a may be identical or different) is chosen from hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more linear or branched C1-C18 alkyl radicals or linear or branched C1-C18 hydroxyalkyl radicals; a linear or branched C1-C18, preferably C6-C12, alkyl radical; a C5-C12 cycloalkyl radical optionally substituted with one or more C1-C4 alkyl radicals; a polyoxyethylenated radical comprising from 1 to 6 ethylene oxide units and the terminal OH group of which is methylated; a radical of formula (19), (20) or (21 ) below: [Formula 19] in which:
  • - Rs is hydrogen or a methyl radical
  • Rg is a C1-C9 alkyl radical
  • - q is an integer ranging from 0 to 3;
  • - r is an integer ranging from 1 to 10;
  • - A is a C4-C8 alkyl radical or a Cs-Cs cycloalkyl radical
  • - B is chosen from: a linear or branched C-i-Cs alkyl radical; a Cs-Cs cycloalkyl radical; an aryl radical optionally substituted with one or more C1-C4 alkyl radicals;
  • R1 denotes a C3-C18 alkyl radical; a C2-C18 alkenyl radical; a residue of formula -CH2- CH(OH)-CH2-OTI in which T1 is a hydrogen atom or a C-i-Cs alkyl radical; a residue of formula (22) below: [Formula 22] in which:
  • R13 denotes a covalent bond; a linear or branched C1-C4 alkyl radical or else a radical of formula -C m iH2mi-0- in which rm is an integer equal to 1 , 2, 3 or 4;
  • - pi is an integer equal to 0, 1 , 2, 3, 4 or 5;
  • radicals R10, R11 and R12 which may be identical or different, denote a C1-C18 alkyl radical; a C1-C18 alkoxy radical or a radical of formula (23):
  • R2 denotes a hydrogen atom, a linear or branched C1-C4 alkyl radical or a C1-C4 alkoxy radical
  • R3 and R4 which may be identical or different, denote a linear or branched C1-C20 alkyl radical
  • R5 represents a hydrogen atom or a phenyl radical optionally substituted with a halogen or with a C1-C4 alkyl radical or with a C1-C4 alkoxy radical;
  • - Re is a linear or branched C-i-Cs alkyl radical or a C1-C3 alkoxy radical, it being understood that, in the latter case, two adjacent Re on one and the same aromatic nucleus can together form an alkylidenedioxy group in which the alkylidene group contains from 1 to 2 carbon atoms, OH, NHCOCH3 or NH2;
  • R7 denotes a hydrogen atom, a C1-C10 alkyl radical, a radical of formula -(CH2CHR5- O)niRs in which ni is a number from 1 to 16, or else a radical having the structure - CH2-CH-(OH)-CH2OTI with Rs and T1 having the same meaning indicated above;
  • - Z represents oxygen, sulfur, -NH- or -NR3 - with R3 representing a linear or branched C1-C20 alkyl radical;
  • - p 0, 1 , 2 or 3;
  • A1 may also be a halogen, a radical -N(Rs)2, it being possible for the two R3 to together form a ring having 4 or 5 carbon atoms, or an -OR3 group, R3 having the same definition as above.
  • radicals X a -R a represents the radical -NH-R a with R a chosen from: a C5-C12 cycloalkyl radical optionally substituted with one or more C1-C4 alkyl radicals; a radical of formula (19), (20) or (21 ) above in which:
  • - B is a C1-C4 alkyl radical
  • X a -R a represent the radical -O-R a with R a , which may be identical or different, chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals; a linear or branched C1-C18 alkyl radical; a C5-C12 cycloalkyl radical optionally substituted with one or more C1-C4 alkyl radicals; a radical of formula (19), (20) or (21 ) above in which:
  • - B is a C1-C4 alkyl radical
  • a second more particularly preferred family of compounds of formula (10) is that consisting of the 1 ,3,5-triazine derivatives described in document EP- A-0 570 838, which corresponds to the 1 ,3,5-triazines of formula (10) in which Ai, A2 and A3 are of formula (11 ) and have all of the following characteristics:
  • X a -R a represents the radical -NH-R a with R a chosen from: a linear or branched C1-C18 alkyl radical; a C5-C12 cycloalkyl radical optionally substituted with one or more C1-C4 alkyl radicals; a radical of formula (19), (20) or (21) above in which:
  • - B is a C1-C4 alkyl radical
  • X a -R a being the radical -O-R a with R a , which may be identical or different, chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals; a linear or branched C1-C18 alkyl radical; a C5-C12 cycloalkyl radical optionally substituted with one or more C1-C4 alkyl radicals; a radical of formula (19), (20) or (21) above in which:
  • - B is a C1-C4 alkyl radical
  • a 1 ,3,5-triazine of this second family that is particularly preferred is 2-[p- (tert-butylamido)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 3V and corresponding to the following formula:
  • a third preferred family of compounds of formula (8) that may be used in the context of the present invention, and which is notably described in document US 4 724 137, corresponds to the 1 ,3,5-triazines of formula (10) in which A1, A2 and A3 are of formula (11 ) and have all of the following characteristics:
  • R - R a which may be identical or different, represent a C6-C12 alkyl radical or a polyoxyethylenated radical comprising from 1 to 6 ethylene oxide units and in which the end OH group is methylated.
  • a 1 ,3,5-triazine of this third family that is particularly preferred is 2,4,6- tris[p-(2'-ethylhexyl-1 '-oxycarbonyl)anilino]-1 ,3,5-triazine or Ethylhexyl Triazone sold notably under the trade name llvinul T 150 by the company BASF and corresponds to the formula below:
  • a fourth preferred family of compounds that may be used in the context of the present invention, and which is notably described in document EP-A- 0775698, is that of the 1 ,3,5-triazines corresponding to formula (10) in which A1 and A2 are of formula (12) and A3 is of formula (18), all having the following characteristics:
  • Ri which may be identical or different, denote a C3- C18 alkyl radical; a C2-C18 alkenyl radical or else a residue of formula -CH2- CH(OH)-CH2-OTI in which T1 is a hydrogen atom or a C-i-Cs alkyl radical;
  • R7 denotes a hydrogen atom or a C1-C10 alkyl radical.
  • a 1 ,3,5-triazine of this fourth family that is particularly preferred is 2,4- bis ⁇ [4-(2-ethylhexyloxy)]-2-hydroxy]phenyl ⁇ -6-(4-methoxyphenyl)-1 ,3,5- triazine or Anisotriazine sold under the trade name Tinosorb S by Ciba Specialty Chemicals and corresponds to the formula below:
  • a fifth preferred family of compounds that may be used in the context of the present invention, and which is notably described in patent applications EP507691 , EP507692, EP790243 and EP944624 and the technical content of which is totally integrated in the present description, is that of the 1 ,3,5-triazines corresponding to formula (10) in which A1, A2 and A3 are of formulae (16) to (20) mentioned above.
  • a 1 ,3,5-triazine of this fifth family which is particularly preferred is 2,4,6- tris(diisobutyl 4'-amino benzalmalonate)-s-triazine which corresponds to the formula below:
  • the triazine UV-screening agent(s) are generally present in the compositions according to the invention in a concentration ranging from 0.1% to 30% by weight, preferably from 0.2% to 20% by weight, and preferentially from 0.5% to 10% by weight, and even more preferentially from 0.5% to 5% by weight relative to the total weight of the composition.
  • composition according to the invention comprises at least one hydrophobically modified polysaccharide, preferably a fructan.
  • Fructans or fructosans are oligosaccharides or polysaccharides comprising a sequence of anhydrofructose units optionally combined with one or more saccharide residues other than fructose.
  • Fructans may be linear or branched.
  • Fructans may be products obtained directly from a plant or microbial source or alternatively products of which the chain length has been modified (increased or decreased) by fractionation, synthesis or hydrolysis, in particular enzymatic.
  • Fructans generally have a degree of polymerization from 2 to about 1000 and preferably from 2 to about 60.
  • the first group corresponds to products of which the fructose units are for the most part linked via (3-2,1 bonds. These are essentially linear fructans such as inulins.
  • the second group also corresponds to linear fructoses, but the fructose units are essentially linked via p-2,6 bonds. These products are levans.
  • the third group corresponds to mixed fructans, i.e. containing p-2,6 and p-2,1 sequences. These are essentially branched fructans, such as graminans.
  • the fructans preferably used in the compositions according to the invention are inulins.
  • Inulin may be obtained, for example, from chicory, dahlia or Jerusalem artichoke.
  • the inulin used in the composition according to the invention is obtained, for example, from chicory.
  • the fructans, in particular the inulins, used in the compositions according to the invention are hydrophobically modified. In particular, they are obtained by grafting hydrophobic chains onto the hydrophilic backbone of the fructan.
  • the hydrophobic chains that may be grafted onto the main chain of the fructan may in particular be linear or branched, saturated or unsaturated hydrocarbon-based chains containing from 1 to 50 carbon atoms, such as alkyl, arylalkyl, alkylaryl or alkylene groups; divalent cycloaliphatic groups or organopolysiloxane chains.
  • These hydrocarbon-based or organopolysiloxane chains may in particular comprise one or more ester, amide, urethane, carbamate, thiocarbamate, urea, thiourea and/or sulfonamide functions such as in particular methylenedicyclohexyl and isophorone; or divalent aromatic groups such as phenylene.
  • the fructan in particular the inulin has a degree of polymerization from 2 to about 1000 and preferably from 2 to about 60, and a degree of substitution of less than 2 on the basis of one fructose unit.
  • the hydrophobic chains contain at least one alkyl carbamate group of formula R-NH-CO-O in which R is an alkyl group containing from 1 to 32 carbon atoms or a hydrophobic ester group which is a C4-C32 alkyl ester, i.e. an -OCO-R group, R being a C4-C32 alkyl.
  • the hydrophobic ester group is a C6-C20 alkyl ester group.
  • the hydrophobic ester group is a C8-C20 alkyl ester group.
  • the hydrophobic ester group is a C10-C20 alkyl ester group. More preferentially, the hydrophobic ester group is a C10-C18 alkyl ester group.
  • the hydrophobic chains are alkyl carbamate groups, in particular Cs-C-is alkyl carbamate groups and more particularly lauryl carbamate groups.
  • hydrophobically modified inulins that may be used in the compositions according to the invention
  • palmitoyl inulin such as those sold under the names Lifidrem INUK and Lifidrem INUM by the company Engelhard
  • inulin lauryl carbamate such as the product sold under the name Inutec SL1 by the company Creachem.
  • the hydrophobically modified fructan is an inulin grafted with lauryl carbamate, which is obtained in particular from the reaction of lauryl isocyanate with an inulin, in particular obtained from chicory.
  • lauryl carbamate obtained in particular from the reaction of lauryl isocyanate with an inulin, in particular obtained from chicory.
  • these compounds include the product sold under the name Inutec SL1 by the company Creachem.
  • the hydrophobically modified polysaccharide may be present in the composition according to the invention in a content ranging from 0.05% to 10% by weight, preferably from 0.05% to 5% by weight, and more preferentially from 0.1 % to 2% by weight relative to the total weight of the composition.
  • the composition according to the invention comprises : a) at least one merocyanine corresponding to formula (3) below, and also the geometric isomer forms, notably the E/E- or E/Z-geometric isomer forms, thereof:
  • A is -O- or -NH
  • R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more O ; b) at least one triazine screening agent chosen from the 1 ,3,5-triazines of formula (10) in which A1, A2 and A3 are of formula (11 ) and have all of the following characteristics:
  • X a -R a represents the radical -NH-R a with R a chosen from: a linear or branched C1-C18 alkyl radical; a C5-C12 cycloalkyl radical optionally substituted with one or more C1-C4 alkyl radicals; a radical of formula (19), (20) or (21 ) above in which:
  • - B is a C1-C4 alkyl radical
  • - R9 is a methyl radical; - the other or other two X a -R a being the radical -O-R a with R a , which may be identical or different, chosen from: hydrogen; an alkali metal; an ammonium radical optionally substituted with one or more alkyl or hydroxyalkyl radicals; a linear or branched Ci- Os alkyl radical; a C5-C12 cycloalkyl radical optionally substituted with one or more Ci- 04 alkyl radicals; a radical of formula (19), (20) or (21 ) above in which:
  • - B is a C1-C4 alkyl radical
  • R9 is a methyl radical ; and c) at least one polysaccharide chosen from fructans modified with linear or branched, saturated or unsaturated hydrocarbon-based chains containing from 8 to 24 carbon atoms, preferably from 8 to 18 carbon atoms.
  • the composition according to the invention comprises : a) at least one merocyanine corresponding to formula (3) below, and also the geometric isomer forms, notably the E/E- or E/Z-geometric isomer forms, thereof:
  • A is -O- or -NH
  • R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more O ; b) the 2,4,6-tris[p-(2'-ethylhexyl-1 '-oxycarbonyl)anilino]-1 ,3,5-triazine corresponding to the formula below: [Formula 25] in which R' denotes a 2-ethylhexyl radical ; and c) at least one polysaccharide chosen from fructans modified with linear or branched, saturated or unsaturated hydrocarbon-based chains containing from 8 to 24 carbon atoms, preferably from 8 to 18 carbon atoms.
  • the composition according to the invention comprises : a) at least one merocyanine corresponding to formula (3) below, and also the geometric isomer forms, notably the E/E- or E/Z-geometric isomer forms, thereof:
  • A is -0- or -NH
  • R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted with one or more O ; b) the 2,4-bis ⁇ [4-(2-ethylhexyloxy)]-2-hydroxy]phenyl ⁇ -6-(4-methoxyphenyl)- 1 ,3,5-triazine corresponding to the formula below: [Formula 26] in which R' denotes a 2-ethylhexyl radical ; and c) at least one polysaccharide chosen from fructans modified with linear or branched, saturated or unsaturated hydrocarbon-based chains containing from 8 to 24 carbon atoms, preferably from 8 to 18 carbon atoms.
  • the composition in accordance with the invention comprises at least one oily phase.
  • oil phase means a phase comprising at least one oil and all of the liposoluble and lipophilic ingredients and the fatty substances used for the formulation of the compositions of the invention.
  • oil is intended to mean any fatty substance that is in liquid form at ambient temperature (20-25°C) and atmospheric pressure (760 mmHg).
  • the oily phase may comprise, in addition to the merocyanine screening agent(s) and the lipophilic additional screening agents according to the invention, at least one volatile or non-volatile hydrocarbon-based oil and/or one volatile and/or non-volatile silicone oil and/or one volatile and/or nonvolatile fluoro oil.
  • silicon oil is understood to mean an oil comprising at least one silicon atom, and in particular at least one Si-0 group.
  • hydrocarbon-based oil is intended to mean an oil mainly containing hydrogen and carbon atoms and optionally one or more heteroatoms, in particular nitrogen and oxygen.
  • these oils may in particular contain one or more carboxyl, ester, ether, hydroxyl functions.
  • fluoro oil refers to an oil comprising at least one fluorine atom.
  • volatile oil is intended to mean an oil that is capable of evaporating on contact with the skin or the keratin fibre in less than one hour, at ambient temperature and atmospheric pressure.
  • volatile oil(s) of the invention are volatile cosmetic oils, which are liquid at ambient temperature, having a non-zero vapour pressure, at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10 -3 to 300 mmHg), in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1 .3 Pa to 1300 Pa (0.01 to 10 mmHg).
  • non-volatile oil means an oil that remains on the skin or the keratin fibre at ambient temperature and atmospheric pressure for at least several hours, and that notably has a vapour pressure of less than 10’ 3 mmHg (0.13 Pa).
  • non-volatile hydrocarbon-based oils that may be used according to the invention, mention may notably be made of:
  • hydrocarbon-based oils of plant origin such as glyceride triesters, which are generally triesters of fatty acids and of glycerol, the fatty acids of which can have varied chain lengths from C4 to C24, it being possible for these chains to be saturated or unsaturated and linear or branched; these oils are in particular wheatgerm oil, sunflower oil, grape seed oil, sesame oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, marrow oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil and musk rose oil; or else caprylic/capric acid triglycerides, such as those sold by
  • synthetic esters such as the oils of formula RCOOR' in which R represents a linear or branched fatty acid residue comprising from 1 to 40 carbon atoms and R' represents a hydrocarbon-based chain that is especially branched, containing from 1 to 40 carbon atoms, with the proviso that R + R' > 10, for instance purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, C12-C15 alkyl benzoate, such as the product sold under the trade name Finsolv TN® or Witconol TN® by the company Witco orTegosoft TN® by the company Evonik Goldschmidt, 2-ethylphenyl benzoate, such as the commercial product sold under the name X- Tend 226® by the company ISP, isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl isononan
  • fatty alcohols that are liquid at ambient temperature, containing a branched and/or unsaturated carbon-based chain containing from 12 to 26 carbon atoms, for instance octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2- butyloctanol or 2-undecylpentadecanol;
  • C12-C22 higher fatty acids such as oleic acid, linoleic acid or linolenic acid
  • carbonates such as dicaprylyl carbonate, such as the product sold under the name Cetiol CC® by the company Cognis; and mixtures thereof.
  • non-volatile hydrocarbon-based oils that may be used according to the invention, preference will be given more particularly to glyceride triesters and in particular to caprylic/capric acid triglycerides, synthetic esters and in particular isononyl isononanoate, oleyl erucate, C12- C15 alkyl benzoate, 2-ethylphenyl benzoate and fatty alcohols, in particular octyldodecanol.
  • hydrocarbon-based oils that may be used according to the invention, mention may be made in particular of hydrocarbon-based oils containing from 8 to 16 carbon atoms and in particular of branched Cs-C alkanes, such as Cs-C isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2, 2, 4,4,6- pentamethylheptane), isodecane or isohexadecane, the oils sold under the Isopar or Permethyl trade names, branched Cs-C esters, isohexyl neopentanoate, and mixtures thereof.
  • Cs-C isoalkanes of petroleum origin also known as isoparaffins
  • isododecane also known as 2, 2, 4,4,6- pentamethylheptane
  • isodecane or isohexadecane the oils sold under the Isopar or Permethyl trade names
  • volatile hydrocarbon-based oils for instance petroleum distillates, in particular those sold under the name Shell Solt® by the company Shell, may also be used.
  • the volatile solvent is chosen from volatile hydrocarbon-based oils containing from 8 to 16 carbon atoms, and mixtures thereof.
  • Non-volatile silicone oils may be notably chosen from non-volatile polydimethylsiloxanes (PDMSs), polydimethylsiloxanes including alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, these groups each containing from 2 to 24 carbon atoms, or phenyl silicones, such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxysilicates.
  • PDMSs non-volatile polydimethylsiloxanes
  • phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, dipheny
  • volatile silicone oils examples include volatile linear or cyclic silicone oils, in particular those with a viscosity ⁇ 8 centistokes (8 x w 6 m 2 /s) and especially containing from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms.
  • volatile silicone oils that may be used in the invention, mention may notably be made of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.
  • R represents an alkyl group containing from 2 to 4 carbon atoms and of which one or more hydrogen atoms may be substituted with a fluorine or chlorine atom.
  • oils of general formula (24) mention may be made of: 3-buty 1-1 ,1 ,1 ,3,5,5,5-heptamethyltrisiloxane,
  • Use may also be made of volatile fluoro oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane, and mixtures thereof.
  • volatile fluoro oils such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane, and mixtures thereof.
  • An oily phase according to the invention may also comprise other fatty substances, mixed with or dissolved in the oil.
  • Another fatty substance that may be present in the oily phase may be, for example:
  • waxes such as lanolin, beeswax, carnauba or candelilla wax, paraffin waxes, lignite waxes, microcrystalline waxes, ceresin or ozokerite, or synthetic waxes, such as polyethylene waxes or Fischer-Tropsch waxes;
  • a pasty compound such as polymeric or non-polymeric silicone compounds, esters of a glycerol oligomer, arachidyl propionate, fatty acid triglycerides and derivatives thereof;
  • the overall oily phase including all the lipophilic substances of the composition capable of being dissolved in this same phase, represents from 5% to 95% by weight and preferentially from 10% to 80% by weight, relative to the total weight of the composition.
  • composition in accordance with the invention may comprise at least one aqueous phase.
  • the aqueous phase contains water and optionally other water-soluble or water-miscible organic solvents.
  • An aqueous phase that is suitable for use in the invention may comprise, for example, a water chosen from a natural spring water, such as water from La Roche-Posay, water from Vittel, water from Saint Gervais Mont Blanc or waters from Vichy, or a floral water.
  • a natural spring water such as water from La Roche-Posay, water from Vittel, water from Saint Gervais Mont Blanc or waters from Vichy, or a floral water.
  • the water-soluble or water-miscible solvents that are suitable for use in the invention comprise short-chain monoalcohols, for example C1-C4 monoalcohols, such as ethanol or isopropanol; diols or polyols, such as ethylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, glycerol and sorbitol, and mixtures thereof.
  • C1-C4 monoalcohols such as ethanol or isopropanol
  • diols or polyols such as ethylene glycol, 1 ,2-propylene glycol, 1 ,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene
  • use may more particularly be made of ethanol, propylene glycol, glycerol, and mixtures thereof.
  • the overall aqueous phase including all the hydrophilic substances of the composition capable of being dissolved in this same phase, represents from 5% to 95% by weight and preferentially from 10% to 80% by weight, relative to the total weight of the composition.
  • compositions according to the invention may also contain one or more additional UV-screening agents, other than the merocyanine derivatives and triazine derivatives as described above, chosen from hydrophilic, lipophilic or insoluble organic UV-screening agents and/or one or more mineral pigments. It will preferentially be constituted of at least one hydrophilic, lipophilic or insoluble organic UV-screening agent.
  • hydrophilic UV-screening agent is intended to mean any cosmetic or dermatological organic or inorganic compound for screening out UV radiation, which can be fully dissolved in molecular form in a liquid aqueous phase or else which can be dissolved in colloidal form (for example in micellar form) in a liquid aqueous phase.
  • lipophilic screening agent is intended to mean any cosmetic or dermatological organic or inorganic compound for screening out UV radiation, which can be fully dissolved in molecular form in a liquid fatty phase or else which can be dissolved in colloidal form (for example in micellar form) in a liquid fatty phase.
  • insoluble UV-screening agent is intended to mean any cosmetic or dermatological organic or inorganic compound for screening out UV radiation which has a solubility in water of less than 0.5% by weight and a solubility of less than 0.5% by weight in the majority of organic solvents such as liquid paraffin, fatty alcohol benzoates and fatty acid triglycerides, for example Miglyol 812® sold by the company Dynamit Nobel.
  • This solubility, determined at 70°C is defined as the amount of product in solution in the solvent at equilibrium with an excess of solid in suspension after returning to ambient temperature. It may be readily evaluated in the laboratory.
  • the additional organic UV-screening agents are chosen in particular from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidenecamphor compounds; benzophenone compounds; (3, [3-diphenylacrylate compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in patent US 5 624 663; benzimidazole derivatives; imidazoline compounds; bis- benzoazolyl compounds, as described in patents EP 669 323 and US 2 463 264; p-aminobenzoic (PABA) compounds; methylenebis(hydroxyphenylbenzotriazole) compounds, as described in patent applications US 5 237 071 , US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 119; benzoxazole compounds, as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844;
  • organic photoprotective agents mention may be made of those denoted hereinbelow under their INCI name.
  • Cinnamic compounds are Cinnamic compounds:
  • Ethylhexyl methoxycinnamate sold in particular under the trade name Parsol MCX® by DSM Nutritional Products,
  • Neo Heliopan E 1000® Isoamyl p-methoxycinnamate, sold under the trade name Neo Heliopan E 1000® by Symrise,
  • Butylmethoxydibenzoylmethane sold in particular under the trade name Parsol 1789® by DSM Nutritional Products,
  • Ethylhexyl dimethyl PABA sold in particular under the name Escalol 507® by ISP,
  • Glyceryl PABA PEG-25 PABA, sold under the name llvinul P 25® by BASF.
  • Octocrylene sold in particular under the trade name llvinul N 539® by BASF
  • Etocrylene sold in particular under the trade name Uvinul N 35® by BASF.
  • Benzophenone-1 sold under the trade name Uvinul 400® by BASF
  • Benzophenone-2 sold under the trade name Uvinul D 50® by BASF
  • Benzophenone-3 or Oxybenzone sold under the trade name Uvinul M 40® by BASF
  • Benzophenone-4 sold under the trade name Uvinul MS 40® by BASF,
  • Benzophenone-6 sold under the trade name Helisorb 11® by Norquay,
  • Benzophenone-8 sold under the trade name Spectra-Sorb UV-24® by American Cyanamid,
  • Benzophenone-9 sold under the trade name Uvinul DS 49® by BASF,
  • Benzophenone-12, n-Hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate sold under the trade name Uvinul A Plus® or, as a mixture with octyl methoxycinnamate, under the trade name Uvinul A Plus B® by the company BASF,
  • Camphor benzalkonium methosulfate manufactured under the name Mexoryl SO® by Chimex,
  • Phenylbenzimidazolesulfonic acid sold in particular under the trade name Eusolex 232® by Merck.
  • Disodium phenyl dibenzimidazole tetrasulfonate sold under the trade name Neo Heliopan AP® by Haarmann and Reimer.
  • Drometrizole trisiloxane sold under the name Si latrizole® by Rhodia Chimie.
  • Methylenebis(benzotriazolyl)tetramethylbutylphenol in particular in solid form, such as the product sold under the trade name Mixxim BB/100® by Fairmount Chemical, or in the form of an aqueous dispersion of micronized particles with an average particle size ranging from 0.01 to 5 pm, more preferentially from 0.01 to 2 pm and more particularly from 0.020 to 2 pm, with at least one alkylpolyglycoside surfactant having the structure C n H2n+iO(C6Hio05)xH, in which n is an integer from 8 to 16 and x is the mean degree of polymerization of the (CeH Os) unit and ranges from 1 .4 to 1 .6, as described in patent GB-A-2 303 549, sold in particular under the trade name Tinosorb M® by BASF, or in the form of an aqueous dispersion of micronized particles with an average particle size ranging from 0.02 to 2 pm, more preferentially from 0.01 to 1.5
  • Neo Heliopan MA® Menthyl anthranilate, sold under the trade name Neo Heliopan MA® by Symrise.
  • Polyorganosiloxane comprising benzalmalonate functions such as Polysilicone-15, sold under the trade name Parsol SLX® by Hoffmann-La Roche.
  • the preferential additional organic screening agents are chosen from:
  • the particularly preferred additional organic screening agents are chosen from:
  • Drometrizole trisiloxane and mixtures thereof.
  • the inorganic UV-screening agents used in accordance with the present invention are metal oxide pigments. More preferentially, the inorganic UV- screening agents of the invention are metal oxide particles with a mean elementary particle size of less than or equal to 0.5 pm, more preferentially between 0.005 and 0.5 pm, even more preferentially between 0.01 and 0.2 pm, better still between 0.01 and 0.1 pm and more particularly between 0.015 and 0.05 pm.
  • They may be chosen in particular from titanium oxide, zinc oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
  • Such coated or uncoated metal oxide pigments are described in particular in patent application EP-A-0 518 773.
  • Commercial pigments that may be mentioned include the products sold by the companies Sachtleben Pigments, Tayca, Merck and Degussa.
  • the metal oxide pigments may be coated or uncoated.
  • the coated pigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (of titanium or aluminium), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
  • compounds such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (of titanium or aluminium), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
  • coated pigments are more particularly titanium oxides that have been coated:
  • silica such as the product Sunveil® from the company Ikeda
  • alumina and aluminum stearate such as the products Microtitanium Dioxide MT 100 T®, MT 100 TX®, MT 100 Z® and MT-01® from the company Tayca, the products Solaveil CT-10 W® and Solaveil CT 100® from the company Uniqema and the product Eusolex T-AVO® from the company Merck, - with silica, alumina and alginic acid, such as the product MT-100 AQ® from the company Tayca,
  • iron oxide and iron stearate such as the product Microtitanium Dioxide MT 100 F® from the company Tayca,
  • TiO2 pigments doped with at least one transition metal such as iron, zinc or manganese and more particularly manganese.
  • said doped pigments are in the form of an oily dispersion.
  • the oil present in the oily dispersion is preferably chosen from triglycerides including those of capric/caprylic acids.
  • the oily dispersion of titanium oxide particles may also comprise one or more dispersants, for instance a sorbitan ester, for instance sorbitan isostearate, or a polyoxyalkylenated fatty acid ester of glycerol, for instance TRI-PPG-3 myristyl ether citrate and polyglyceryl-3 polyricinoleate.
  • the oily dispersion of titanium oxide particles includes at least one dispersant chosen from polyoxyalkylenated fatty acid esters of glycerol. Mention may be made more particularly of the oily dispersion of TiO2 particles doped with manganese in capric/caprylic acid triglyceride in the presence of TRI-PPG-3 myristyl ether citrate and polyglyceryl-3 polyricinoleate and sorbitan isostearate having the INCI name: titanium dioxide (and) TRI-PPG-3 myristyl ether citrate (and) polyglyceryl-3 ricinoleate (and) sorbitan isostearate, for instance the product sold under the trade name Optisol TD50® by the company Croda.
  • the uncoated titanium oxide pigments are sold, for example, by the company Tayca under the trade names Microtitanium Dioxide MT 500 B or Microtitanium Dioxide MT 600 B®, by the company Degussa under the name P 25, by the company Wackher under the name Transparent titanium oxide PW®, by the company Miyoshi Kasei under the name LIFTR®, by the company Tomen under the name ITS® and by the company Tioxide under the name Tioveil AQ.
  • the uncoated zinc oxide pigments are, for example:
  • Nanox® those sold under the name Nanox® by the company Elementis;
  • Nanogard WCD 2025® those sold under the name Nanogard WCD 2025® by the company Nanophase Technologies.
  • coated zinc oxide pigments are, for example:
  • Oxide Zinc CS-5® those sold under the name Oxide Zinc CS-5® by the company Toshibi (ZnO coated with polymethylhydrogenosiloxane);
  • Nanogard Zinc Oxide FN® those sold under the name Nanogard Zinc Oxide FN® by the company Nanophase Technologies (as a 40% dispersion in Finsolv TN®, C12-C15 alkyl benzoate);
  • Daitopersion Zn-30® and Daitopersion Zn-50® sold under the name Daitopersion Zn-30® and Daitopersion Zn-50® by the company Daito (dispersions in cyclopolymethylsiloxane/oxyethylenated polydimethylsiloxane, containing 30% or 50% of zinc oxides coated with silica and polymethylhydrogenosiloxane);
  • the uncoated cerium oxide pigments may be, for example, those sold under the name Colloidal Cerium Oxide® by the company Rhone-Poulenc.
  • the uncoated iron oxide pigments are sold, for example, by the company Arnaud under the names Nanogard WCD 2002® (FE 45B®), Nanogard Iron FE 45 BL AQ, Nanogard FE 45R AQ® and Nanogard WCD 2006® (FE 45R®) or by the company Mitsubishi under the name TY-220®.
  • the coated iron oxide pigments are sold, for example, by the company Arnaud under the names Nanogard WCD 2008 (FE 45B FN)®, Nanogard WCD 2009® (FE 45B 556®), Nanogard FE 45 BL 345® and Nanogard FE 45 BL® or by the company BASF under the name Transparent Iron Oxide®.
  • metal oxides especially of titanium dioxide and of cerium dioxide, including the equal-weight mixture of titanium dioxide and cerium dioxide coated with silica, sold by the company Ikeda under the name Sunveil A®, and also the mixture of titanium dioxide and zinc dioxide coated with alumina, silica and silicone, such as the product M 261® sold by the company Sachtleben Pigments, or coated with alumina, silica and glycerol, such as the product M 211® sold by the company Sacht
  • coated or uncoated titanium oxide pigments are particularly preferred.
  • the additional UV-screening agents according to the invention can be present in the composition according to the invention in a content ranging from 0.1 % to 60% by weight and in particular from 5% to 30% by weight relative to the total weight of the composition.
  • composition in accordance with the present invention may also comprise conventional cosmetic adjuvants chosen in particular from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, basifying or acidifying agents or any other ingredient commonly used in the cosmetic and/or dermatological field.
  • conventional cosmetic adjuvants chosen in particular from organic solvents, ionic or non-ionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, bas
  • C1-C4 monoalkanols as defined above and in particular short-chain C2-C8 polyols, such as glycerol or diols, such as caprylyl glycol, 1 ,2-pentanediol, propanediol, butanediol, glycols and glycol ethers, such as ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol
  • carboxyvinyl polymers such as the Carbopols® (Carbomers) and the Pemulens, such as Pemulen TR1® and Pemulen TR2® (acrylate/C -Cso alkyl acrylate copolymer); polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel 305® (CTFA name: polyacrylamide/C -u isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyl taurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; 2- acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, such as the poly(2-acrylamido-2- methylpropanesulfonic acid) sold by the company Hoechst under the trade name Hostacerin AMPS® (
  • examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
  • examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines, such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide or potassium hydroxide.
  • the cosmetic composition comprises one or more basifying agents chosen from alkanolamines, in particular triethanolamine, and sodium hydroxide.
  • the pH of the composition in accordance with the invention is generally between 3 and 12 approximately, preferably between 5 and 11 approximately and even more particularly from 6 to 8.5.
  • active agents for caring for keratin materials such as the skin, the lips, the scalp, the hair, the eyelashes or the nails
  • compositions in accordance with the invention can be aqueous or anhydrous.
  • compositions When the compositions are aqueous, they contain at least one aqueous phase.
  • compositions in accordance with the invention can then be in purely aqueous form, that is to say they comprise an amount of fatty phase of less than 10 % by weight, preferably less than 5 % by weight, and even more preferably less than 2 % by weight relative to the total weight of the composition.
  • the composition in accordance with the invention is essentially aqueous, that is to say that it is free of fatty phase.
  • compositions according to the invention may be prepared according to the techniques that are well known to those skilled in the art. They may in particular be 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 or a cream gel.
  • a simple or complex emulsion O/W, W/O, O/W/O or W/O/W
  • anhydrous composition means a composition containing less than 1 % by weight of water, or even less than 0.5% water, and especially free of water, the water not being added during the preparation of the composition but corresponding to the residual water provided by the mixed ingredients. They may optionally be packaged in aerosol form and may be in the form of a mousse or a spray.
  • compositions in the form of oil-in-water or water-in-oil emulsions are of the paddle or impeller, rotor-stator and HPH type.
  • the emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or non-ionic emulsifiers, used alone or as a mixture.
  • the emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained (W/O or O/W emulsion).
  • W/O emulsifying surfactants examples include alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, sold under the name DC 5225 C® by the company Dow Coming, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Coming; cetyldimethicone copolyol, such as the product sold under the name Abil EM 90R® by the company Goldschmidt, and the mixture of cetyldimethicone copolyol, of polyglyceryl isostearate (4 mol) and of hexyl laurate, sold under the name Abil WE 09® by the company Goldschmidt.
  • silicone surfactants for instance
  • non-silicone emulsifying surfactants in particular alkyl esters or ethers of sorbitan, of glycerol, of polyol or of sugars.
  • Polyol alkyl esters that may in particular be mentioned include polyethylene glycol esters, for instance PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135® by the company ICI.
  • glycerol and/or sorbitan esters examples include polyglyceryl isostearate, such as the product sold under the name Isolan Gl 34® by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987® by the company ICI; sorbitan glyceryl isostearate, such as the product sold under the name Arlacel 986® by the company ICI, and mixtures thereof.
  • non-ionic emulsifying surfactants examples include polyoxyalkylenated (more particularly polyoxyethylenated and/or polyoxypropylenated) esters of fatty acids and of glycerol; oxyalkylenated esters of fatty acids and of sorbitan; polyoxyalkylenated (in particular polyoxyethylenated and/or polyoxypropylenated) esters of fatty acids, optionally in combination with an ester of a fatty acid and of glycerol, such as the PEG-100 stearate/glyceryl stearate mixture sold, for example, by the company ICI under the name Arlacel 165; oxyalkylenated (oxyethylenated and/or oxypropylenated) ethers of fatty alcohols; esters of sugars, such as sucrose stearate; or ethers of fatty alcohol and of sugar, in particular
  • the aqueous phase of this emulsion may comprise a non-ionic vesicular dispersion prepared according to known processes (Bangham, Standish and Watkins, J. Mol. Biol. 13, 238 (1965), FR 2 315 991 and FR 2 416 008).
  • compositions according to the invention find their application in a large number of treatments, in particular cosmetic treatments, for the skin, the lips and the hair, including the scalp, in particular for protecting and/or caring for the skin, the lips and/or the hair, and/or for making up the skin and/or the lips.
  • compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, the lips, the nails, the hair, the eyelashes, the eyebrows and/or the scalp, in particular care products, antisun products and makeup products.
  • the cosmetic compositions according to the invention may be used, for example, as a makeup product.
  • Another subject of the present invention is constituted of a non- therapeutic cosmetic process for caring for and/or making up a keratin material, which consists in applying, to the surface of said keratin material, at least one composition according to the invention as defined above.
  • the cosmetic compositions according to the invention may be used, for example, as a care product and/or antisun product for the face and/or body, with a liquid to semi-liquid consistency, such as milks, more or less smooth creams, gel-creams or pastes. They may optionally be packaged in aerosol form and may be in the form of a mousse or a spray.
  • compositions according to the invention in the form of vaporizable fluid lotions in accordance with the invention are applied to the skin or hair in the form of fine particles by means of pressurizing devices.
  • the devices in accordance with the invention are well known to those skilled in the art and comprise non-aerosol pumps or “atomizers”, aerosol containers comprising a propellant and aerosol pumps using compressed air as propellant. These devices are described in patents US 4 077 441 and US 4 850 517.
  • compositions packaged in aerosol form in accordance with the invention generally contain conventional propellants, for instance hydrofluoro compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane. They are preferably present in amounts ranging from 15% to 50% by weight relative to the total weight of the composition.
  • the invention also relates to a cosmetic assembly comprising: i) a container delimiting one or more compartment(s), said container being closed by a closing member and optionally being unsealed; and ii) a makeup and/or care composition in accordance with the invention placed inside said compartment(s).
  • the container may be, for example, in the form of a jar or a box.
  • the closing member may be in the form of a lid comprising a cap mounted so as to be able to move by translation or by pivoting relative to the container housing said makeup and/or care composition(s).
  • composition ingredients are given as weight percentages of starting material relative to the total weight of the composition.
  • the completion of the alkylation reaction can be monitored for example by methods such as TLC, GC or HPLC.
  • 101.00 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1 -one are alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 g of 2-cyano-N-(3-methoxypropyl)acetamide in approximately equimolar proportions in the presence of a base and optionally of a solvent.
  • the crude product (15) is obtained in the form of a dark brown oil.
  • composition preparation method :
  • the aqueous phase A is prepared by mixing the starting materials by heating to 70°C until a homogeneous phase is obtained.
  • Phase B is prepared likewise, by heating to 80°C until a homogeneous phase is obtained.
  • the emulsion is prepared by introducing phase B into phase A with vigorous stirring for 10 minutes. The heating is stopped. Phase C is introduced, followed by phase D, and the mixture is left to homogenize for 10 minutes. Phase E is then added. Finally, phase F is introduced at 25°C. The final emulsion is characterized by drops of 1 pm to 20 pm.
  • the product is transferred onto a white cotton fabric by means of a 25 cm 2 PMMA plate.
  • the amount deposited is eguivalent to 2mg/cm 2 .
  • the fabric is left to dry for 24 h in the open air, then machine washed (Colour programme 40°C - duration 1 h 30) with a liguid detergent.
  • the staining capacity is evaluated 24 hours after washing via the measurement of the AE obtained by means of a chromameter (Konica Minolta Sensing Europe BV).
  • AE ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇
  • AE is calculated from the variations AL, Aa and Ab according to the following formula:
  • AL represents the difference between the value of L of the non-stained area and the value of L of the stained area after 24 hours following washing of the fabric
  • Aa represents the difference between the value of a of the non-stained area and the value of a of the stained area after 24 hours following washing of the fabric
  • Ab represents the difference between the value of b of the non-stained area and the value of b of the stained area after 24 hours following washing of the fabric.
  • compositions 1 to 5 below were prepared according to the protocol detailed above.
  • compositions 2 and 3 according to the invention in which methoxypropylamino cyclohexenylidene ethoxyethyl cyanoacetate (Compound 25) is used as UVA-screening agent leave fewer marks after washing than Reference Composition 1 which does not contain UVA- screening agents or than Comparative Compositions 4 and 5 in which diethylamino hydroxybenzoyl hexyl benzoate (for example llvinul A+ from BASF) or butyl methoxydibenzoylmethane (for example Parsol 1789 from DSM) is used as UVA-screening agent.
  • diethylamino hydroxybenzoyl hexyl benzoate for example llvinul A+ from BASF
  • butyl methoxydibenzoylmethane for example Parsol 1789 from DSM
  • compositions 6 to 9 below were prepared according to the protocol detailed above. [Table 10]
  • compositions 6 to 9 are described in the table below.

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Abstract

Composition cosmétique ou dermatologique comprenant une mérocyanine, un filtre UV du type triazine et un polysaccharide modifié par des chaînes hydrophobes. La présente invention concerne une composition, de préférence une composition cosmétique ou dermatologique, comprenant : a) au moins une mérocyanine de formule (1) ou (2) ci-dessous : (1) et (2) et b) au moins un filtre UV du type triazine; et c) au moins un polysaccharide modifié par des chaînes hydrophobes. La présente invention concerne également l'utilisation d'au moins une telle mérocyanine de formule (1) ou (2) pour réduire la coloration de tissus, en particulier de vêtements, après lavage.
PCT/EP2021/085679 2020-12-18 2021-12-14 Composition cosmétique comprenant une mérocyanine, un filtre uv du type triazine et un polysaccharide modifié par des chaînes hydrophobes WO2022129039A1 (fr)

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EP21824598.3A EP4262714A1 (fr) 2020-12-18 2021-12-14 Composition cosmétique comprenant une mérocyanine, un filtre uv du type triazine et un polysaccharide modifié par des chaînes hydrophobes
MX2023007221A MX2023007221A (es) 2020-12-18 2021-12-14 Composicion cosmetica que comprende una merocianina, un agente bloqueador de rayos ultravioleta (uv) de tipo triazina y un polisacarido modificado con cadenas hidrofobas.

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FR2013603A FR3117825A1 (fr) 2020-12-18 2020-12-18 Composition cosmétique ou dermatologique comprenant une mérocyanine, un filtre UV triazine, et un polysaccharide modifié par des chaînes hydrophobes
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FR3132637A1 (fr) * 2022-02-15 2023-08-18 L'oreal Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique

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FR3132637A1 (fr) * 2022-02-15 2023-08-18 L'oreal Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique

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