Composition for the stabilization of photosensitive compounds

Abstract

Composition for Stabilizing Photosensitive Compounds. The present invention relates to a composition for stabilizing at least one photosensitive compound selected from colorants, perfumes, ultraviolet filters, or antioxidants against the effects of ultraviolet radiation. This composition comprises a combination of: - at least one compound (A) of the following formula (I): - at least one ultraviolet absorber (B), which is butyl methoxydibenzoylmethane; - at least one ultraviolet absorber (C), which is diethylhexyl syringylidenemalonate. The present invention also relates to the use of this composition for stabilizing said photosensitive compound and a cosmetic formulation comprising it. Figure for abstract: none

Description

Title of the invention: Composition for the stabilization of photosensitive compounds

[0001] The subject of the present invention is a composition for stabilizing photosensitive, thermosensitive and / or oxidation-sensitive compounds against the effects of ultraviolet radiation.

[0002] The present invention also relates to the use of said compositions for stabilizing a photosensitive compound, and in particular the coloring and / or the perfume of a formulation, such as a cosmetic formulation.

[0003] It is known that UV rays (wavelengths from 100 to 400 nm) can initiate radical chain reactions that lead to the decomposition of photosensitive molecules. The majority of cosmetic products are formulated with compounds sensitive to UV rays, in particular dyes and perfumes. Indeed, a portion of UV-B rays (290 to 320 nm) and UV-A rays (320 to 400 nm) can affect the integrity of these photosensitive molecules. Products packaged in transparent or semi-transparent packaging are particularly subject to exposure to UV rays.

[0004] There are specific packagings which provide more effective protection, in particular packagings made of polyethylene, polyethylene terephthalate, polypropylene or polyvinyl chloride, treated with anti-UV, but their cost is very high, and phenomena of transfer of UV filters from the packaging to the formulas are known.

[0005] A more economical solution consists of adding UV absorbers to the cosmetic formula. These compounds must, however, be chosen carefully to ensure protection across the entire UV spectrum. Furthermore, certain UV filters, such as avobenzone, are themselves photosensitive and must be stabilized by other UV absorbers. Finally, these UV absorbers must also be chosen carefully to ensure the maintenance of the physicochemical properties of the formulas (such as color, odor, transparency, etc.) in which they are incorporated and to stabilize them for a sufficiently long time to ensure the product's lifespan.

[0006] Application EP 2 923 690 describes a composition comprising ethyl-hexyl-salicylate, butyl methoxydibenzoylmethane and diethylhexyl syringylidenemalonate for stabilizing photosensitive compounds. However, ethyl-hexyl-salicylate is suspected of being an endocrine disruptor.

[0007] The present invention therefore aims to provide a composition for stabilizing photosensitive, thermosensitive and / or oxidation-sensitive compounds, such as dyes, perfumes, antioxidants or ultraviolet filters, against the effects of ultraviolet radiation, and at a reduced cost.

[0008] One of the aims of the invention is in particular to provide a composition for stabilizing coloring and / or perfumes against the harmful effects of ultraviolet radiation.

[0009] Another aim of the invention is to provide a composition for stabilizing in particular the coloring and / or the perfumes of a formulation such as a cosmetic formulation.

[0010] Composition

[0011] To this end, according to a first object, the present invention relates to a composition for the stabilization of at least one photosensitive compound chosen from dyes, perfumes, ultraviolet filters or antioxidants, against the effects of ultraviolet radiation, said composition comprising a combination of:

[0012] - at least one compound (A) of the following formula (I):

[0013] [Chem.l]

[0014] in which

[0015] - Ri is H or an alkyl group, linear or branched, comprising from 1 to 6 atoms of carbon, preferably 1 to 4 carbon atoms,

[0016] - R2 is H or an alkyl group, linear or branched, comprising from 1 to 8 atoms of carbon, preferably from 1 to 6 carbon atoms,

[0017] - at least one ultraviolet absorber (B) which is butyl methoxydibenzoylmethane, and

[0018] - at least one ultraviolet absorber (C) which is diethylhexyl syringylidene- malonate.

[0019] The inventors have advantageously shown that the stabilizing composition according to the invention makes it possible to stabilize a photosensitive compound chosen from dyes, perfumes, ultraviolet filters or antioxidants, against the effects of ultraviolet radiation. The stabilizing composition stabilizes in particular the coloring and / or perfumes of a formulation in which it has been added. Better stabilization has in particular been observed with the composition according to the invention compared to other stabilizing compositions, in particular those of the prior application EP 2 923 690.

[0020] The compositions according to the invention advantageously make it possible to avoid the premature aging of cosmetic formulations exposed to natural or artificial light, which can lead to oxidation, reduction, catalysis phenomena, etc. These compositions according to the invention therefore make it possible in particular to protect cosmetic formulations packaged in transparent packaging.

[0021] The embodiments described below can be combined with each other in any technically possible combination.

[0022] According to one embodiment, the present invention relates to a composition as defined above, comprising:

[0023] - from 55% to 85% by weight of compound (A), relative to the total weight of (A), (B) and (C);

[0024] - from 6% to 25% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0025] - from 5% to 20% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0026] In the context of the invention, and unless otherwise stated, the term "total weight of (A), (B) and (C)" means the sum of the weight of the compound (A), the UV absorber (B) and the UV absorber (C).

[0027] In the context of the invention, and unless otherwise stated, the term "ultraviolet absorber" (or UV absorber) means a chemical compound capable of absorbing ultraviolet radiation in a range between 4 and 400 nm, in particular between 200 and 400 nm, and most particularly between 290 and 400 nm (UV-A and UV-B). In the context of the invention, and unless otherwise stated, the term "photosensitive compound" means a compound capable of being chemically degraded following exposure to UV radiation emanating from natural or artificial light.

[0028] According to one embodiment, in the above-mentioned formula (I), Ri represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, preferably from 1 to 3, and even more preferably 2 carbon atoms.

[0029] According to one embodiment, in the above-mentioned formula (I), R2 represents a linear or branched alkyl group comprising from 2 to 6 carbon atoms, preferably from 3 to 5, and even more preferably 4 carbon atoms.

[0030] According to a preferred embodiment, the compound (A) is diethylhexyl maleate of the following formula (Ia):

[0032] According to a preferred embodiment, the composition of the invention comprises a single compound of formula (I). In particular, the composition of the invention comprises diethylhexyl maleate as a compound of formula (I).

[0033] The ultraviolet absorber (B) of the composition is 4-(tert-butyl)-4'-methoxy dibenzoylmethane (also called butyl-methoxy-dibenzoylmethane or Avobenzone), and corresponds to the following formula:

[0034] [Chem.3] OO

[0035] Compound (C) of the composition is diethylhexyl syringylidenemalonate of the following formula:

[0036] [Chem.4]

[0037] According to one embodiment, the stabilizing composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, preferably less than 0.1% by weight, of ethyl-hexyl-salicylate relative to the weight of (A), (B) and (C).

[0038] Preferably, the stabilizing composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, more preferably less than 0.1% by weight, of an ultraviolet absorber from the salicylate family corresponding to the following formula (X):

[0039] [Chem.5] O

[0040] in which R3 is selected from the group consisting of:

[0041] - a linear or branched alkyl group comprising from 2 to 12 carbon atoms, preferably from 3 to 8 carbon atoms, said alkyl group being optionally interrupted by at least one oxygen atom, said alkyl group being optionally substituted by a hydroxy or alkoxy group comprising from 1 to 8 carbon atoms;

[0042] - an arylalkyl group comprising from 7 to 10 carbon atoms optionally substituted by an alkyl group comprising from 1 to 10 carbon atoms;

[0043] - an amine optionally substituted by at least one hydroxy group,

[0044] relative to the weight of (A), (B) and (C).

[0045] Preferably, the stabilizing composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, more preferably less than 0.1% by weight of salicylate or mixture of salicylates relative to the weight of (A), (B) and (C).

[0046] According to a particular embodiment, the composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, preferably less than 0.1% of 2-ethylhexyl-methoxycinnamate, or even cinnamate relative to the weight of (A), (B) and (C). 2-ethylhexyl-methoxycinnamate is suspected of being an endocrine disruptor by European regulatory authorities.

[0047] According to a particular embodiment, the stabilizing composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, preferably less than 0.1% by weight of ethyl-hexyl-salicylate relative to the weight of the composition.

[0048] According to a particular embodiment, the stabilizing composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, preferably less than 0.1% by weight of ultraviolet absorber from the salicylate family corresponding to formula (X) relative to the weight of the composition.

[0049] According to a particular embodiment, the stabilizing composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, preferably less than 0.1% by weight of salicylate or mixture of salicylates relative to the weight of the composition.

[0050] According to a particular embodiment, the composition comprises less than 1% by weight, preferably less than 0.5% by weight, preferably less than 0.2% by weight, preferably less than 0.1% of 2-ethylhexyl-methoxycinnamate, or even cinnamate relative to the weight of the composition.

[0051] According to a particular embodiment, the stabilizing composition is free of ethyl-hexyl-salicylate, or even free of ultraviolet absorber of the sa- family. licylates corresponding to the formula (X), or even free of salicylate.

[0052] According to one embodiment, the stabilizing composition is free of 2-ethylhexyl-methoxycinnamate, preferably free of cinnamate.

[0053] Ranges and ratios

[0054] According to one embodiment, the present invention relates to a composition as defined above, comprising:

[0055] - from 55% to 85% by weight of compound (A), relative to the total weight of (A), (B) and (C);

[0056] - from 6% to 25% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0057] - from 5% to 20% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0058] According to another embodiment, the composition as defined previously comprises:

[0059] -from 61% to 81% by weight of compound (A), relative to the total weight of (A), (B) and (C);

[0060] - from 10% to 22% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0061] - from 6% to 17% by weight of ultraviolet absorber (C), relative to the weight of (A), (B) etc).

[0062] According to another embodiment, the composition as defined previously comprises:

[0063] - from 64% to 84% by weight of compound (A), relative to the total weight of (A), (B) and (C);

[0064] - from 11% to 20% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0065] - from 5% to 16% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0066] According to another embodiment, the composition as defined previously comprises:

[0067] - from 65% to 80% by weight of compound (A), relative to the total weight of (A), (B) and (C);

[0068] - from 13% to 18% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0069] - from 6% to 17% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0070] According to another embodiment, the composition as defined previously comprises:

[0071] - from 70% to 80% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0072] - from 12% to 18% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0073] - from 5% to 16% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0074] According to another embodiment, the composition as defined previously comprises:

[0075] - from 65% to 75% by weight of compound (A), relative to the total weight of (A), (B) and (C);

[0076] - from 13% to 20% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0077] - from 9% to 15% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0078] According to another embodiment, the composition as defined previously comprises:

[0079] - from 70% to 75% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0080] - from 15% to 20% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0081] - from 9% to 13% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0082] According to another embodiment, the composition as defined previously comprises:

[0083] - from 71% to 73% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0084] - from 15% to 19% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and

[0085] - from 10% to 13% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0086] According to another embodiment, the composition as defined previously comprises:

[0087] - from 70 to 71.5% by weight of ultraviolet absorber (A), relative to the total weight of the ultraviolet absorbers (A), (B) and (C);

[0088] - from 15 to 17% by weight of ultraviolet absorber (B), relative to the total weight of the ab ultraviolet sorbers (A), (B) and (C); and

[0089] - from 11.5 to 15% by weight of ultraviolet absorber (C), relative to the total weight of the ultraviolet absorbers (A), (B) and (C).

[0090] Preferably, the composition as defined above comprises:

[0091] - 71.5% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0092] - 17% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (This

[0093] - 11.5% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0094] Alternatively, the composition as defined above comprises:

[0095] - 70% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0096] - 15% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (This

[0097] - 15% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0098] According to one embodiment, the composition according to the invention comprises from 55% to 85% by weight of compound (A), relative to the total weight of (A), (B) and (C), preferably from 61% to 81%, even more preferably from 71% to 73%.

[0099] According to one embodiment, the composition according to the invention comprises from 6% to 25% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C), preferably from 10% to 22%, and even more preferably from 15% to 19%.

[0100] According to one embodiment, the composition according to the invention comprises 5% to 20% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C), preferably from 6% to 17%, and even more preferably from 10% to 13%.

[0101] According to another embodiment, the composition as defined previously consists of:

[0102] - 71.5% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0103] - 17% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (This

[0104] - 11.5% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0105] According to another embodiment, the composition as defined previously consists of:

[0106] - 70% by weight of compound (A), relative to the weight of (A), (B) and (C);

[0107] - 15% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (This

[0108] - 15% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

[0109] According to one embodiment, in the composition, the ratio of compounds (A): (B) is from about 3:1 to about 15:1, preferably from about 3:1 to about 10:1. In particular, the ratio of compounds (A): (B) is from about 4:1 to about 6:1.

[0110] According to one embodiment, in the composition, the ratio of ultraviolet absorbers (B): (C) is from approximately 1:0.3 to approximately 1:5, preferably from about 1:0.4 to about 1:1. In particular, the ratio of ultraviolet absorbers (B):(C) is from about 1:0.5 to about 1:0.8.

[0111] According to one embodiment, in the composition, the ratio of compounds (A): (B): (C) is from about 4: 1: 0.4 to about 15: 1: 0.4, preferably from about 6: 1: 0.4 to about 10: 1: 0.4.

[0112] According to one embodiment, the composition comprises at least 25%, in particular at least 50%, preferably at least 75% by cumulative weight of (A), (B) and (C) relative to the weight of the composition.

[0113] Other possible components

[0114] According to one embodiment, the composition according to the invention further comprises at least one antioxidant compound chosen from the group consisting of: thiols and derivatives; phenols, polyphenols and derivatives, such as flavonoids, phenolic acids, tannins, anthocyanins; [3-carotene (provitamins A); tocopherols (vitamin E) or its esters such as alpha-tocopherol, gamma-tocopherol, delta-tocopherol.

[0115] According to one embodiment, the ratio between the weight of antioxidant compound and the cumulative weight of (A), (B) and (C) is from 1:15 to 1:1.

[0116] According to one embodiment, the composition according to the invention further comprises at least one compound with chelating properties chosen from the group consisting of: ascorbic acid and its esters such as sodium or calcium ascorbate; diacetyl 5-6-1-ascorbic acid, palmityl 6-1-ascorbic acid, citric acid and citrates such as sodium, potassium and calcium; tartaric acid and tartrates such as sodium, potassium; phytic acid and its salts; di-aminotetracarboxylic acids such as edetic acid; butylhydroxyanisole and butylhydroxytoluol; octyl or dodecyl gallates; sodium, potassium or calcium lactates; lecithins; glutathione, enzymes such as catalase, superoxide dismutases and certain peroxidases.

[0117] According to one embodiment, the ratio between the weight of compound with chelating properties and the cumulative weight of (A), (B) and (C) is from 1:15 to 1:6.

[0118] According to one embodiment, the composition according to the invention further comprises at least one surfactant, synthetic or biosourced, chosen from the group consisting of: anionic surfactants, such as carboxylic acid salts, sulfonated derivatives, sulfated derivatives and phosphate derivatives; amphoteric surfactants, such as betaines, imidazoline derivatives, polypeptides; and non-ionic surfactants, such as non-ionics with an ester bond, ether bond or amide bond.

[0119] According to one embodiment, the ratio between the cumulative weight of (A), (B) and (C) and the weight of surfactant is from 1:1 to 1:20.

[0120] According to one embodiment, the composition according to the invention further comprises at least at least one solvent selected from the group consisting of: hydrocarbons, in particular aliphatic or aromatic hydrocarbons or halogenated hydrocarbons, alcohols, glycols, ketones, esters, ethers and glycol ethers.

[0121] According to one embodiment, the ratio between the cumulative weight of (A), (B) and (C) and the weight of solvent is from 1:1 to 1:20.

[0122] According to one embodiment, the composition according to the invention consists of diethylhexyl maleate, butyl methoxydibenzoylmethane and diethylhexyl syringylidenemalonate and optionally a solvent. The ranges of proportions for the components described above are applicable.

[0123] According to one embodiment, the composition according to the invention is in liquid form.

[0124] Use

[0125] The present invention also relates to the use of a composition, as described above, for stabilizing a photosensitive, thermosensitive and / or oxidation-sensitive compound, such as a dye, a perfume, an antioxidant or an ultraviolet filter, from the effects of ultraviolet radiation.

[0126] According to the invention, among the photosensitive compounds, mention may be made of ultraviolet filters, such as: 4-aminobenzoic acid (PABA), benzalkonium camphor methosulfate, homosalate, 2-Hydroxy-4-methoxybenzophenone (benzophenone-3), phenylbenzimidazole sulfonic acid, terephthalylidene dicamphor sulfonic acid, butyl methoxydibenzoylmethane, benzylidene camphor sulfonic acid, octocrylene, polyacrylamidomethyl benzylidene camphor, ethylhexyl methoxycinnamate, PEG-25 of 4-aminobenzoic acid, isoamyl p-methoxycinnamate, ethylhexyl triazone, drometrizole trisiloxane, diethylhexyl-butamido-triazone, 4-methylbenzylidene camphor, 3-benzylidene camphor, ethylhexyl salicylate, ethylhexyl dimethyl PABA, 5-Benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid (Benzophenone-4), 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid sodium salt (Benzophenone-5), bis-benzotriazolyl tetramethylbutylphenol methylene,phenyl-dibenzimidazole disodium tetrasulfonate, bis-ethylhexyloxyphenol methoxyphenyl triazine, polysilicone-15 or diethylamino-hydroxybenzoyl-hexyl benzoate.

[0127] According to one embodiment, the photosensitive compound is a dye, a perfume, an antioxidant or an ultraviolet filter.

[0128] According to one embodiment, the present invention relates to the use of a composition, as described above, for stabilizing the coloring of a formulation from the effects of ultraviolet radiation.

[0129] According to one embodiment, the present invention relates to the use of a com position, as described above, to stabilize a colorant of a formulation from the effects of ultraviolet radiation. According to one embodiment, the composition according to the invention makes it possible to avoid the degradation of the coloring of a formulation by ultraviolet radiation.

[0130] According to one embodiment, the present invention relates to the use of a composition, as described above, for stabilizing a perfume of a formulation, from the effects of ultraviolet radiation. According to one embodiment, the composition according to the invention makes it possible to avoid the degradation of a perfume of a formulation by ultraviolet radiation.

[0131] Examples of fragrance ingredients include those included in the EPA Fragrance Ingredient List of March 30, 2012 (http: / / www.epa.gov / opprd001 / inerts / fmaingredient.pdf).

[0132] Examples of colorants include organic colorants or natural colorants, such as madder, soluble carmine, caramel, chlorophyll or cucurmin.

[0133] Plus particulièrement, à titre de colorants, on peut citer : Acid Black 1, Acid Black 52, Acid Blue 3, Acid Blue 9, Acid Blue 9 Ammonium Sait, Acid Blue 62, Acid Blue 74, Acid Green 1, Acid Green 25, Acid Green 50, Acid Orange 6, Acid Orange 7, Acid Red 18, Acid Red 27, Acid Red 33, Acid Red 51, Acid Red 73, Acid Red 87, Acid Red 92, Acid Red 95, Acid Red 184, Acid Red 195, Acid Violet 9, Acid Violet 43, Acid Yellow 3, Acid Yellow 23, Acid Yellow 73, Basic Blue 6, Acid Yellow 73 Sodium Sait, Aka2, Aka3, Akal02, Akal04(l), Akal05(l), Akal06, Aka201, Aka202, Aka203, Aka204, Aka205, Aka206, Aka207, Aka208, Aka213, Aka214, Aka215, Aka218, Aka219, Aka220, Aka221, Aka22, Aka225, Aka226, Aka227, Aka228, Aka230(l), Aka230(2), Aka231, Aka232, Aka401, Aka404, Aka405, Aka501, Aka502, Aka503, Aka504, Aka505, Annatto, Anthocyanins, Aol, Ao2, Ao201, Ao202, Ao203, Ao204, Ao205, Ao403, Ao404, Astaxanthin, Basic Blue 6, Basic Blue 41, Basic Yellow 11, Beetroot, Blue l,Blue 4, Brilliant Black 1,Bromocresol Green, Bromothymol Blue, Brown 1, Capsanthin / Capsorubin, Caramel, Carminé, Beta-Carotene, Carotenolds, Chlorophyllin-Copper Complex, Cl 10006, Cl 10020, Cl 10316, Cl 11680, Cl 11710, Cl 11725, Cl 11920, Cl 12010, Cl 12085, Cl 12120, Cl , 12150, Cl 12370, Cl 12420, Cl 12480, Cl 12490, Cl 12700, Cl 13015, Cl 14270, Cl 14700, Cl 14720, Cl 14815, Cl 15510, Cl 15525, Cl 15580, Cl 15620, Cl 15630, Cl 15800, Cl 15850, Cl 15865, Cl 15880, Cl 15980, Cl 15985, Cl 16035, Cl 16185, Cl 16230, Cl 16255, Cl 16290, Cl 17200, Cl 18050, Cl 18130, Cl 18690, Cl 18736, Cl 18820, Cl 18965, Cl 19140, Cl 20040, Cl 20170, Cl 20470, Cl 21100, Cl 21108, Cl 21230, Cl 24790, Cl 26100, Cl 27290, Cl 27755, Cl 28440, Cl 40215, Cl 40800, Cl 40820, Cl 40825, Cl 40850, Cl 42045, Cl 42051, Cl 42053, Cl 42080, Cl 42090, Cl 42100, Cl 42170, Cl 42510, Cl 42520, Cl 42735, Cl 44045, Cl 44090, Cl 45100, Cl 45190, Cl 45220, Cl 45350, Cl 45370, Cl 45380, Cl 45396, Cl 45405, Cl 45410, Cl 45425, Cl 45430, Cl 47000, Cl 47005, Cl 50325, Cl 50420, Cl 51319, Cl 58000, Cl 59040, Cl 60724, Cl 60725, Cl 60730, Cl 61565, Cl 61570, Cl 61585, Cl 62045, Cl 69800, Cl 69825, Cl 71105, Cl 73000, Cl 73015, Cl 73360, Cl 73385, Cl 73900, Cl 73915, Cl 74100, Cl 74160, Cl 74180, Cl 74260, Cl 75100, Cl 75120, Cl 75125, Cl 75130, Cl 75135, Cl 75170, Cl 75300, Cl 75470, Cl 75810, Cl 77000, Cl 77002, Cl 77004, Cl 77007, Cl 77015, Cl 77120, Cl 77163, Cl 77220, Cl 77231, Cl 77267, Cl 77268:1, Cl 77288, Cl 77289, Cl 77346, Cl 77400, Cl 77480, Cl 77713, Cl 77742, Cl 77745, Cl 77820,Cl 77947, Cochineal, Crocus Sativus Flower Extract, Curry Red, Daidai201, Daidai203, Daidai204, Daidai205, Daidai206, Daidai207, Daidai401, Daidai402, Daidai403, Dihydroxyacetone, Direct BLue 86, Dunaliella Bardawil Powder, Erythrulose, Ext. Violet 2, Ext. Yellow 7, Ext. Yellow 7 Lake, Fast Green FCF, Fluorescent Brightener 230, Fluorescent Brightener 236, Gardénia Florida Extract, Green 3, Green 5, Green 6, Green 8, Haematococcus Pluvialis Powder, Hae-matoxylon Campechianum Wood Extract, Henna, Katsu201, Ki4, Ki5, Ki201, Ki202(l), Ki202(2), Ki203, Ki204, Ki205, Ki401, Ki402, Ki403(l), Ki404, Ki405, Ki406, Ki407, Kuro401, Lactoflavin, Lawsone, Midori3, Midori201, Midori202, Midori204,k Midori205, Midori401, Midori402, Murasaki201, Murasaki401, Natural Red 26, Ninhydrin, Orange 4, Orange 5, Orange 10, Orange 11, Ponceau SX, Pyro-phyllite, Red 4, Red 17, Red 21, Red 22, Red 27, Red 28,Red 30, Red 31,Red 33, Red 34,Red 36, Red 40, Solvent Green 3, Solvent Green 7, Solvent Orange 1, Solvent Red 1, Solvent Red 3, Solvent Red 23, Solvent Red 24, Solvent Red 43, Solvent Red 48, Solvent Red 49:1, Solvent Red 72, Solvent Red 73, Solvent Violet 13, Solvent Yellow 18, Solvent Yellow 29, Solvent Yellow 33, Solvent Yellow 44, Sunset Yellow, Vat Red 1, Violet 2, Yellow 5, Yellow 6, Yellow 7, Yellow 8, Yellow 10, Yellow 11. ,

[0134] Selon un mode préféré, à titre de colorants, on peut citer le Red 33 (CI 17200), le Red 4 (CI 14700), le Ext. Violet 2 (CI 60730) et le Yellow 5 (CI 19140).

[0135] In particular, the present invention relates to the use of a composition, as described above, for stabilizing a colorant or a perfume in a cosmetic formulation, more particularly a care or hygiene product, a perfume or an eau de toilette. Preferably, the cosmetic formulation is a shampoo, a shower gel, a mouthwash, a lotion, a serum, or a gel.

[0136] In order to preserve the coloring from the effects of UV rays, the aforementioned stabilizing composition is added to a formulation in an appropriate quantity. This quantity will depend on the nature of the colorants, the nature of the perfume, the presence of compounds that can cause oxidation, reduction, catalysis phenomena and the presence of various photosensitive compounds, but also on the degree of exposure of the formulation to UV rays. It will therefore depend in particular on the transparency of the container to UV rays and the lifespan of the formulation.

[0137] According to one embodiment, the composition according to the invention is introduced into a formulation in a content of from 0.01% to 3%, preferably from 0.05% to 2%, and more particularly from 0.1% to 1% by weight relative to the total weight of the formulation.

[0138] Formulation

[0139] The invention also relates to a formulation comprising the composition according to the invention.

[0140] In particular, stabilization of the color and / or perfumes has advantageously been obtained with a quantity of the order of only 0.3% of the composition according to the invention, which allows an interesting cost / effectiveness compromise.

[0141] In particular, the invention relates to a formulation comprising from 0.1 to 5% by weight of the composition of the aforementioned type, preferably from 0.01% to 3% by weight, preferably from 0.05% to 2% by weight, and more particularly from 0.1% to 1% by weight relative to the total weight of the formulation.

[0142] Generally, the composition comprises at least one photosensitive compound chosen from dyes, perfumes, ultraviolet filters or antioxidants.

[0143] The embodiments described above, in particular for the stabilizing composition and the photosensitive compound, are applicable.

[0144] The formulation according to the invention may be a cosmetic, dermo-cosmetic or pharmaceutical formulation.

[0145] The present invention also relates to a method for stabilizing photosensitive, thermosensitive and / or oxidation-sensitive compounds, such as dyes, perfumes, antioxidants or ultraviolet filters, said method comprising the addition of a stabilizing composition as described above in a formulation comprising said photosensitive compounds.

[0146] The invention is illustrated by the following examples: Examples

[0147] Suppliers - Diethylhexyl maleate: Innospec Performance Chemicals - Isopropoyl phthalimide & Butylphthalimide: Phoenix Chemical - Avobenzone: Merck, Ashland, Symrise, DSM - Diethylhexyl syringylidene malonate: Merck - Red 33 (CI 17200): Sensient Cosmetic Technologies - Red 4 (CI 14700): Sensient Cosmetic Technologies - Ext. Violet 2 (CI 60730): Sensient Cosmetic Technologies - Perfume I: Sensient Fragrances

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] - Perfume II: Sensient Fragrances - Perfume III: Sensient Fragrances Colorants A! : Yellow 5 - CI 19140 Bp Red 33 - CI 17200 G: Red 4 - CI 14700 Dp Ext. Violet 2 - CI 60730 Perfumes - Perfume I: Mineral Splash 546202426 - Perfume II: Oriental Infinity 546202425 - Perfume III: Diamond Beauty 546202258 - Perfume IV: Ambrettia Bella 546202209 Example 1: Preparation of stabilizing compositions Compositions II and I2 according to the invention and comparative compositions C1 to C3 of Tables 1 to 4 were prepared: [Tables 1] Composition II (invention) % Diethylhexyl Maléate 71,5 Avobenzone 17 Diéthylhexyl Syringylidènemalonate 11,5 [Tableaux2] Composition 12 (invention) % Diethylhexyl Maléate 70 Avobenzone 15 Diéthylhexyl Syringylidènemalonate 15 [Tableaux3] Composition Cl (comparative) % Ethylhexyl Salicylate 71,5 Avobenzone 17 Diéthylhexyl Syringylidènemalonate 11,5

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] [Tableaux4] Composition C2 (comparative) % Avobenzone 17% Diéthylhexyl Syringylidènemalonate 11.5% Eau 71.5% [Tableaux5] Composition C3 (comparative) % Isopropoyl phthalimide & Butylph-thalimide 71,5 Avobenzone 17 Diéthylhexyl Syringylidènemalonate 11,5 The compositions do not include any other compounds than those mentioned, and the proportions are therefore relative to the total weight of the composition. In particular, the comparative Cl composition corresponds to the preferred composition of the earlier application EP 2 923 690. The preparation of compositions II, 12, Cl and C3 is carried out hot (approximately 80°C) and with stirring for 30 minutes. For composition C2, there is no prior preparation because avobenzone and diethylhexyl syringylidenemalonate are insoluble in water: each component is introduced separately into the finished perfumed and colored formulas of example 2. Example 2: Preparation of formulations Several formulations have been prepared by combining at room temperature a perfume, a colorant and a stabilizing composition as follows: - Perfume I + Colorant Ai, Bb Ci or Di + Stabilizing composition II, 12, Cl, or C3 + Ethanol + Water - Perfume II + Colorant Di + Stabilizing composition II, Cl, C2 or C3 + Ethanol + Water - Perfume III + Colorant Bi or Ci + Stabilizing composition II, 12, Cl, C2 or C3 + Ethanol + Water - Perfume IV + Colorant Bi + Stabilizing composition 12 + Ethanol + Water These formulations included: 1% of a 0.1% aqueous solution of an Ab Bb Ci or Di dye; 8% perfume I, II, III or IV; 0.3% of a stabilizing composition chosen from one of the stabilizing compositions II, 12 or Cl to C3 above;

[0166] 75% ethanol; and

[0167] 15.7% water.

[0168] Control formulations free from stabilizing composition were prepared comprising

[0169] 1% of a 0.1% aqueous solution of an Ab Bb Ci or Di dye;

[0170] 8% of perfume I, II, III or IV;

[0171] 75% perfume; and

[0172] 16% water.

[0173] Each formulation was prepared in 3 copies and placed: - in the dark (witnesses); - in an accelerated UV aging chamber (Suntest) for 24 hours; - in natural light.

[0174] The Suntest is a CPS+ model from Atlas / Ametek, equipped with a 1500 W xenon lamp fitted with a glass filter allowing the simulation of natural sunlight behind 3 mm thick glazing. The illumination intensity was set to its maximum level (60 W / m2).

[0175] After passing through the Suntest, the discoloration and degradation of the perfume were evaluated for each of the samples.

[0176] Discoloration was assessed using a transmission spectrocolorimeter, model CM-5 from Konica Minolta. The AE values ​​of the samples, after 24 and 48 hours of UV exposure, were measured. The AE value corresponds to the colorimetric difference between the samples and the control (not exposed to the Suntest) in the L*a*b* color space, according to the following formula:

[0177] [Math.l] △k* = 7^^

[0178] where: i î , &1 are the coordinates in the L*a*b* color space of the first color to be compared (witness) and £2, a.7, those of the second (sample).

[0179] The lower the AE values, the less the coloring of the formulations is degraded.

[0180] Results obtained for the formulations prepared with the compositions IL 12. CL C2 and C3:

[0181] The following two tables correspond respectively to two series of tests, carried out separately. The series are not comparable with each other.

[0182] [Tableauxô] Perfume Color Control (AE) Composition Il (AE) Composition Cl (AE) Composition C2 (AE) Composition C3 (AE) Perfume I Bi 47.5 17.0 42.5 42.1 29.7 Ci 29.9 20.4 29.6 29.6 29.8 Ü! 25.9 9.36 14.48 15.40 23.48 Parfum II Ü! 22.0 13.8 17.6 15.4 23.9 Perfume III B! 48.08 4.68 5.07 5.01 38.37 c, 30.0 2.56 3.01 2.75 5.11

[0183] [Tables?] Perfume Color Control (AE) Composition II (AE) Composition 12 (AE) Composition Cl (AE) Perfume I Ai 39.3 36.9 37.4 38.0 Ü! 23.1 7.3 7.5 14.3 Perfume III B! 47.1 5.5 ND 6.1 Perfume IV B! 45.6 38.0 36.7 39.4

[0184] Conclusion:

[0185] The results in Table 6 demonstrate that composition II according to the invention comprising the diethylhexyl maleate / avobenzone / diethylhexyl syringylidenemalonate combination allows better stabilization of the formulations compared to compositions comprising only avobenzone and diethylhexyl syringylidenemalonate, or comprising ethylhexyl salicylate or a mixture of isopropoyl phthalimide and butylphthalimide instead of diethylhexyl maleate.

[0186] Diethylhexyl maleate clearly contributes to the stabilization of formulations, and improves the performance of avobenzone and diethylhexyl syringylidenemalonate.

[0187] The results in Table 7 demonstrate that composition 12 comprising different amounts of diethylhexyl maleate, avobenzone and diethylhexyl syringylidenemalonate, also makes it possible to stabilize formulations in a similar manner to composition II, and stabilizes better than composition C1 which comprises ethylhexyl salicylate instead of diethylhexyl maleate.

Claims

Claims

1. Composition for stabilizing at least one photosensitive compound chosen from dyes, perfumes, ultraviolet filters or antioxidants, against the effects of ultraviolet radiation, said composition comprising a combination of: - at least one compound (A) of the following formula (I): [Chem. 6] \____. nn „____ / / \ / 7 \\ / \ r2 O—vy—O r2 CO in which: - Ri is H or a linear or branched alkyl group comprising from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, - R2 is H or a linear or branched alkyl group comprising from 1 to 8 carbon atoms, preferably from 1 to 6 carbon atoms, - an ultraviolet absorber (B) which is butyl methoxydibenzymethane, and - an ultraviolet absorber (C) which is diethylhexyl syringylidene malonate.

2. Composition according to claim 1, comprising: - from 55% to 85% by weight of compound (A), relative to the total weight of compounds (A), (B) and (C); - from 6% to 25% by weight of ultraviolet absorber (B), relative to the total weight of compounds (A), (B) and (C); and - from 5% to 20% by weight of ultraviolet absorber (C), relative to the total weight of compounds (A), (B) and (C).

3. A composition according to claim 1 or 2, wherein compound (A) is diethylhexyl maleate of the following formula (Ia): [Chem. 7] y--7 0-^ ^-0 X (Ia)

4. A composition according to any one of claims 1 to 3, comprising: - from 64% to 84% by weight of compound (A), relative to the total weight of (A), (B) and (C); - from 11% to 20% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and - from 5% to 16% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

5. Composition according to any one of claims 1 to 4, comprising: - from 70% to 80% by weight of compound (A), relative to the total weight of (A), (B) and (C); - from 12% to 18% by weight of ultraviolet absorber (B), relative to the total weight of (A), (B) and (C); and - from 5% to 16% by weight of ultraviolet absorber (C), relative to the total weight of (A), (B) and (C).

6. Composition according to any one of claims 1 to 5, comprising: - from 70 to 71.5% by weight of ultraviolet absorber (A), relative to the total weight of the ultraviolet absorbers (A), (B) and (C); - from 15 to 17% by weight of ultraviolet absorber (B), relative to the total weight of the ultraviolet absorbers (A), (B) and (C); and - from 11.5 to 15% by weight of ultraviolet absorber (C), relative to the total weight of the ultraviolet absorbers (A), (B) and (C).

7. A composition according to any one of claims 1 to 6, comprising less than 1% by weight of ethyl-hexyl-salicylate relative to the total weight of (A), (B) and (C), preferably which is free of ethyl-hexyl-salicylate.

8. Use of a composition according to any one of claims 1 to 7, for stabilizing a photosensitive, thermosensitive and / or oxidation-sensitive compound, such as a dye, a perfume, an antioxidant or an ultraviolet, from the effects of ultraviolet radiation.

9. Use according to claim 8, wherein the photosensitive compound is a dye or a perfume.

10. Cosmetic formulation comprising from 0.1 to 5% by weight of the composition according to one of claims 1 to 7, preferably from 0.01% to 3% by weight, preferably from 0.05% to 2% by weight, and more particularly from 0.1% to 1% by weight, relative to the total weight of the formulation.