WO2023281224A1 - Composition cosmetique solaire contenant des acides amines analogues de la mycosporine - Google Patents
Composition cosmetique solaire contenant des acides amines analogues de la mycosporine Download PDFInfo
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- WO2023281224A1 WO2023281224A1 PCT/FR2022/051365 FR2022051365W WO2023281224A1 WO 2023281224 A1 WO2023281224 A1 WO 2023281224A1 FR 2022051365 W FR2022051365 W FR 2022051365W WO 2023281224 A1 WO2023281224 A1 WO 2023281224A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 146
- 150000001413 amino acids Chemical class 0.000 title abstract description 11
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 238000012216 screening Methods 0.000 claims abstract description 20
- 230000005855 radiation Effects 0.000 claims abstract description 18
- -1 amino acid analogue of mycosporin Chemical class 0.000 claims description 97
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- 229910052760 oxygen Inorganic materials 0.000 description 1
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- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
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- 239000011713 pantothenic acid Substances 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
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- 229920009537 polybutylene succinate adipate Polymers 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
- IHWPQGIYXJKCOV-UHFFFAOYSA-N pongamol Natural products C1=CC=2OC=CC=2C(OC)=C1C(=O)C=C(O)C1=CC=CC=C1 IHWPQGIYXJKCOV-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002662 propylthiouracil Drugs 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940108325 retinyl palmitate Drugs 0.000 description 1
- 235000019172 retinyl palmitate Nutrition 0.000 description 1
- 239000011769 retinyl palmitate Substances 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229960002718 selenomethionine Drugs 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 230000036555 skin type Effects 0.000 description 1
- YRWWOAFMPXPHEJ-OFBPEYICSA-K sodium L-ascorbic acid 2-phosphate Chemical compound [Na+].[Na+].[Na+].OC[C@H](O)[C@H]1OC(=O)C(OP([O-])([O-])=O)=C1[O-] YRWWOAFMPXPHEJ-OFBPEYICSA-K 0.000 description 1
- 229940048058 sodium ascorbyl phosphate Drugs 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 230000036561 sun exposure Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ZRVDANDJSTYELM-FXAWDEMLSA-N totarol Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)C1=C2C(C(C)C)=C(O)C=C1 ZRVDANDJSTYELM-FXAWDEMLSA-N 0.000 description 1
- 229940074347 totarol Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- ZRVDANDJSTYELM-UHFFFAOYSA-N trans-totarol Natural products C1CC2C(C)(C)CCCC2(C)C2=C1C(C(C)C)=C(O)C=C2 ZRVDANDJSTYELM-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- 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
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
Definitions
- UV radiation consists of light with a wavelength between 100 nm and 400 nm, traditionally divided into 3 subgroups: UV-A (400-315 nm), UV- B (315-280 nm) and UV-C (280-100 nm). Short-wavelength UV-C is the most energetic and harmful UV.
- UV-A and UV-B are filtered by the ozone layer of the atmosphere and do not reach the surface of the Earth in considerable quantity.
- Most skin damage is caused by UV-A and UV-B.
- UV-B rays induce the production of the skin's natural pigment called “melanin”. This is the origin of the phenomenon commonly called “tanning”.
- UV-B also stimulates cells to produce a thicker epidermis.
- the reactions described above constitute a defense mechanism of the body against UV radiation.
- the high UV-B energy generates molecular disorders (DNA alteration and protein damage) which, in the long term, saturate and stop the nuclear DNA repair system. This leads to permanent mutations in the genome of the affected cells, which are at the origin of skin cancers. It is then a direct toxicity of UV-B.
- UV-A As for UV-A, it is known that they penetrate the deep layers of the skin, where they produce deleterious effects, in particular within the connective tissue and on the blood vessels. They are in particular at the origin of the phenomenon called “heliodermia", that is to say the premature actinic aging of the skin.
- UV-B rays are the main cause of skin cancer, UV-A rays also have an indirect contribution to this type of damage. Indeed, UV-A and UV-B are at the origin of the production of free radicals, in particular ROS (Reactive Oxygen Species or reactive oxygen species (ROS)). These are very unstable molecules with a very short half-life, of the order of a nanosecond to a millisecond.
- ROS Reactive Oxygen Species or reactive oxygen species
- ROS are capable of damaging intracellular structures (DNA, membranes, intracellular proteins, etc.) as well as extracellular structures (components of the extracellular matrix such as collagen fibers, etc.). ROS also exert an indirect harmful action, by causing the oxidation of membrane lipids, which induces the formation of reactive carbonyl species which contribute to amplifying tissue and cellular damage. It is therefore necessary to fight against the harmful effects of UV radiation, in particular UV-A and UV-B, taking into account inter-individual differences such as skin type (phototype) and sun exposure times. For this reason, sunscreen compositions have been developed to ensure photo-protection of areas subject to UV radiation.
- compositions are in the form of a lotion, an oil, an emulsion of the oil-in-water or water-in-oil type, a mousse, a gel, a stick or a spray.
- They contain a cosmetically acceptable carrier and one or more chemical filters or mineral screens at various concentrations.
- Mineral sunscreens including zinc oxides and titanium dioxides, provide UV protection by reflecting sunlight. They therefore act as localized mirrors on the surface of the skin.
- Mineral screens at least in the micrometer formula, are safe for human use and pose no health risk.
- the chemical or organic filters are mostly lipophilic and therefore lend themselves to implementation in highly water-resistant compositions. From a galenic point of view, the compositions based on organic screening agents are, in general, more appreciated than those based on mineral screens, which makes it possible to improve compliance by users. In Europe, all the organic filters or mineral screens, authorized by the regulations, are included in a list (appendix VI of the European Directive on cosmetic products). This is a list currently grouping around thirty compounds according to their INCI designation, from which the cosmetics industry must draw in order to formulate sun protection products. However, this list is not set in stone and is constantly evolving according to the results of scientific research.
- MAA mycosporin analog amino acids
- MAAs are small heterocyclic molecules ( ⁇ 400 Da) comprising cyclohexenone or cyclohexenimine chromophores.
- MAAs are naturally found as secondary metabolites in marine organisms, such as corals, algae and cyanobacteria, so they are expected to be eco-compatible and respectful of aquatic ecosystems.
- document EP2855441 discloses a family of compounds, of MAA type, having the following general formula IE:
- the aim of the present invention is to overcome the drawbacks of the state of the art, by proposing a composition, in particular ecobiological, comprising MMA and whose SPF is compatible with a topical sunscreen application.
- Presentation of the invention The Applicant has observed that, quite surprisingly, the fact of combining MMA with at least two organic UVB and/or broad-spectrum filters in the presence of at least one organic UVA filter makes it possible to obtain an SPF of the combination of a value greater than that of the sum of the respective SPFs of the MAAs and the organic filters. This combination therefore lends itself to their use in compositions with high sun protection at relatively low levels of organic screening agents.
- the invention relates to a composition, in particular a cosmetic or dermatological composition, comprising: at least one amino acid analogue of mycosporin called “MAA”; -at least two UVB organic filters and/or at least two broad-spectrum organic filters; -at least one organic UVA filter.
- MAA amino acid analogue of mycosporin
- the invention relates to a composition, in particular a cosmetic or dermatological composition, comprising: - at least one amino acid analog of mycosporin called "MAA" chosen from the group consisting of molecules A of formula IA or a of its acceptable salts, and/or the group consisting of molecules B of formula IB or one of its acceptable salts, said formula IA being: Wherein: R1 is hydrogen; alkyl; alkenyl; alkynyl; aryl; heterocycle; cycloalkyl; alkoxy; alkanoyl; hydroxyl; a sulfo group; a halogen group; a phosphono group; an ester group; a carboxylic acid group; a phenyl group; an amino group; an alkylated fatty acid chain or a polyether; R2 is alkyl; alkenyl; alkynyl; aryl; heterocycle; cycloalkyl; alkoxy; alkanoyl; a
- the composition according to the invention is ecobiological.
- ecobiological composition we mean respectful of people, their interactions with the world, and the planet.
- the MAAs according to the invention are known to those skilled in the art and described for example in patent application WO2013/181741 which details their process for obtaining and purifying them.
- R1 is an alkoxy group of the [CH3]-[CH2]nO- type, where “n” is between 0 and 10.
- the MAA according to formula IA corresponds to the molecule of formula IIA1 below:
- Formula IIA1 This molecule of formula IIA1: [N-[(3E)-3-[(4-methoxyphenyl)imino]-5,5-dimethyl-1-cyclohexen-1-yl]-Glycine, corresponding to CAS number 1509902-01- 5] is marketed by ELKIMIA Inc. under the INCI designation methoxyphenylimino dimethylcyclohexene glycine.
- the MAA according to formula IA corresponds to the molecule of formula IIA2 below:
- Formula IIA2 This molecule of formula IIA2: [N-[3-[(4-methoxyphenyl)amino]-5,5-dimethyl-2-cyclohexen-1-ylidene]-, ethyl ester, [N(E)]-Glycine, corresponding with CAS number 2640340-86-7] is available from the company SENSIENT Inc. under the trade name SENSISORBTM BIOMIM (INCI: methoxyphenylimino dimethylcyclohexenyl ethyl glycinate).
- the MAA according to formula IB corresponds to the molecule of formula IIB1 below:
- Formula IIB1 This molecule of formula IIB1 [3,5,6,7-tetrahydro-6,6-dimethyl-8-[[4-(octyloxy)phenyl]amino]-2H-1,4-Benzothiazine-3-carboxylic acid, corresponding with CAS number 1629023-01-3] is marketed by the company ELKIMIA Inc. under the INCI designation caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid.
- the MAA according to formula IB corresponds to the molecule of formula IIB2 below:
- Formula IIB2 This molecule of formula IIB2 [3,5,6,7-tetrahydro-8-[(4-methoxyphenyl)amino]-6,6-dimethyl-2H-1,4-Benzothiazine-3-carboxylic acid corresponding to CAS number 1629023 -04-6] is marketed by the company ELKIMIA Inc. under the INCI designation methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid.
- the MAA according to formula IB corresponds to the molecule of formula IIB3 below.
- the compositions according to the invention contain at least two MAAs as defined previously, in particular chosen from molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid and methoxyphenylimino dimethylcyclohexenyl ethyl glycinate as well as possibly the compound corresponding to CAS number 2699128-33-9.
- the compositions according to the invention contain at least three MAAs.
- salts within the meaning of the invention, is meant any pharmacologically or cosmetically acceptable salt of MAA, such as, for example, salts of the sulfate, citrate, acetate, oxalate, chloride, bromide, iodide, nitrate, bisulfate, phosphate, isonicotinate, lactate, salicylate, citrate, tartrate, oleate, tannate, pantothenate, bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucuronate, saccharate, formate, benzoate, glutamate, methanesulfonate, ethanesulfonate, benzenesulfonate, p- toluenesulfonate, pamoate and hydroxy-3-naphthoate.
- the MAA(s) represent(s) between 0.1% and 20% by mass relative to the total mass of the composition, preferably between 0.5% and 10%, even more advantageously between 1 and 2%.
- organic sunscreen denotes organic UVB filters, organic UVA filters and broad-spectrum organic filters.
- organic UVB filter within the meaning of the invention, is meant any organic sunscreen, whether hydrophilic or lipophilic, which absorbs mainly or exclusively in UVB.
- the organic UVB filter is chosen from salicylates.
- the organic UVB filter is chosen from the compounds corresponding to the following INCI designations: ethylhexyl salicylate and homosalate or else phenylbenzimidazole sulphonic acid or ethylhexyl triazone.
- a source of the latter is the raw material UVINULTM T150 marketed by the company BASF.
- the organic UVB filter corresponding to the INCI designation phenylbenzimidazole sulfonic acid, for its part, is available from the company AAKO BV under the name AakoSun PBSA.
- said at least one organic UVB filter represents between 1% and 20% by mass relative to the total mass of the composition, preferably between 2% and 15%.
- organic UVA filter within the meaning of the invention, is meant any organic sunscreen, whether hydrophilic or lipophilic, which absorbs mainly or exclusively in UVA.
- the composition according to the invention comprises at least one UVA sunscreen chosen from the group comprising the compounds corresponding to the following INCI designations: butyl methoxydibenzoylmethane, diethylamino hydroxybenzoyl hexyl benzoate, bis-(diethylaminohydroxybenzoyl benzoyl) piperazine, disodium phenyl dibenzimidazole tetrasulfonate, especially butyl methoxydibenzoylmethane and diethylamino hydroxybenzoyl hexyl benzoate.
- UVA sunscreen chosen from the group comprising the compounds corresponding to the following INCI designations: butyl methoxydibenzoylmethane, diethylamino hydroxybenzoyl hexyl benzoate, bis-(diethylaminohydroxybenzoyl benzoyl) piperazine, disodium phenyl dibenzimidazole tetrasul
- the UVA filters according to the invention correspond to the raw material Parsol 1789® (INCI: butyl methoxydibenzoylmethane) marketed by the company DSM; the raw material UVINULTM A+ (INCI: diethylamino hydroxybenzoyl hexyl benzoate) marketed by the company BASF; the raw material C1332TM [INCI: bis-(diethylaminohydroxybenzoyl benzoyl) piperazine; CAS number 919803-06-8] marketed by the company BASF; or else the material Neo HeliopanTM AP corresponding to the INCI designation disodium phenyl dibenzimidazole tetrasulfonate, and marketed by the company SYMRISE.
- said at least one organic UVA screening agent represents between 1% and 10% by weight relative to the total weight of the composition, preferably between 2% and 7%.
- broad-spectrum organic filter within the meaning of the invention, is meant any organic sunscreen, whether hydrophilic or lipophilic, which absorbs both UVB and UVA rays.
- the composition according to the invention comprises at least one broad-spectrum sunscreen chosen from the group comprising the compounds corresponding to the following INCI designations: bis ethylhexyloxyphenol methoxyphenyl triazine, diethylhexyl butamido triazone, tris-biphenyl triazine, phenylene bis-diphenyltriazine, methylene bis-benzotriazolyl tetramethylbutylphenol and drometrizole trisiloxane, in particular bis-ethylhexyloxyphenol methoxyphenyl triazine, diethylhexyl butamido triazone, tris-biphenyl triazine, methylene bis-benzotriazolyl tetramethylbutylphenol.
- INCI designations bis ethylhexyloxyphenol methoxyphenyl triazine, diethylhexyl butamido triazone,
- sunscreens are available from the following suppliers: - PARSOLTM Shield marketed by the company SYMRISE and corresponding to the INCI designation: bis ethylhexyloxyphenol methoxyphenyl triazine; - UVASORBTM HEB marketed by the company SIGMA 3V and corresponding to the INCI designation: diethylhexyl butamido triazone; - TINOSORBTM A2B marketed by BASF and corresponding to the INCI designation tris-biphenyl triazine; - the TRIASORBTM marketed by the company PLANTES & INDUSTRIE and corresponding to the INCI designation: phenylene bis-diphenyltriazine (CAS number 55514-22-2); - MEXORYLTM XL, corresponding to the INCI designation: drometrizole trisiloxane; - TINOSORBTMM marketed by BASF and corresponding to the INCI designation: methylene bis-
- said at least one broad-spectrum organic screening agent represents between 1% and 15% by mass relative to the total mass of the composition, preferably between 2% and 10%.
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9, -at least two organic UVB filters; -at least one organic UVA filter.
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least two broad-spectrum organic filters; -at least one organic UVA filter.
- MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxy
- the composition according to the invention comprises: - at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least one organic UVB filter; at least one broad-spectrum organic filter; -at least one organic UVA filter.
- MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetra
- the composition according to the invention comprises: - at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least one organic UVB filter; -at least two broad-spectrum organic filters; -at least one organic UVA filter.
- MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethylt
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least two organic UVB filters; at least one broad-spectrum organic filter; -at least one organic UVA filter.
- MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least 2 UVB filters corresponding to the following INCI designations: octyl salicylate and homosalate; - at least the UVA organic filter corresponding to the following INCI designation: butyl methoxydibenzoylmethane.
- MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations me
- the composition according to the invention comprises as MAAs and organic sunscreens: - an MAA chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as optionally the compound corresponding to CAS number 2699128-33-9, advantageously methoxyphenylimino dimethylcyclohexene glycine; - 2 UVB filters corresponding to the following INCI designations: octyl salicylate and homosalate; - an organic UVA filter corresponding to the following INCI designation: butyl methoxydibenzoylmethane.
- an MAA chosen
- the composition according to the invention comprises as MAAs and organic sunscreens: - two MAAs chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9, advantageously methoxyphenylimino dimethylcyclohexene glycine and methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid and methoxyphenylimino dimethylcyclohexenyl ethyl glycinate; - 2 UVB filters corresponding to the following
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least 2 UVB filters, corresponding to the following INCI designations: octyl salicylate and homosalate; - at least the UVA organic filter corresponding to the following INCI designation: diethylamino hydroxybenzoyl hexyl benzoate.
- MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least two broad-spectrum filters corresponding to the following INCI designations: diethylhexyl butamido triazone and bis-ethylhexyloxyphenol methoxyphenyl triazine; -at least one UVA sunscreen chosen from the group comprising the compounds corresponding to the following INCI designations: butyl me
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least two broad-spectrum filters corresponding to the following INCI designations: diethylhexyl butamido triazone and bis-ethylhexyloxyphenol methoxyphenyl triazine; -at least one UVA sunscreen corresponding to the following INCI designation: diethylamino hydroxybenzoyl
- the composition according to the invention comprises as MAAs and organic sunscreens: - an MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as optionally the compound corresponding to CAS number 2699128-33-9, advantageously methoxyphenylimino dimethylcyclohexene glycine; - two broad-spectrum filters corresponding to the following INCI designations: diethylhexyl butamido triazone and bis-ethylhexyloxyphenol methoxyphenyl triazine; -
- the composition according to the invention comprises: --at least one MAA as defined above, in particular chosen from the group consisting of the corresponding molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid , methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; at least broad-spectrum filters corresponding to the following INCI designations: diethylhexyl butamido triazone and bis-ethylhexyloxyphenol methoxyphenyl triazine; at least the organic UVB filter corresponding to the following INCI designation: ethylhexyl triazone;
- the composition according to the invention comprises: at least one MAA as defined above, in particular chosen from the group consisting of the corresponding molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate and possibly the compound corresponding to CAS number 2699128-33-9; at least the broad-spectrum organic screening agents corresponding to the following INCI designations: diethylhexyl butamido triazone and bis-ethylhexyloxyphenol methoxyphenyl triazine; at least the organic UVB filter corresponding to the following INCI designation: ethylhexyl triazone; -
- the composition according to the invention is free of at least one, alternatively sunscreens corresponding to the following INCI designations: 4-methylbenzylidene camphor, 3-methylbenzylidene camphor, benzophenone-2, benzophenone-3, benzophenone-4, ethylhexyl methoxycinnamate, isoamyl methoxycinnamate, octocrylene, octyl dimethyl PABA.
- the composition additionally includes at least one sunscreen solubilizer.
- the term “solubilizer” denotes a compound which makes it possible to solubilize, disperse and/or dissolve at least one triazine-derived sunscreen in an effective and lasting manner, that is to say by stabilizing it in its solubilized form and by preventing or reducing its recrystallization or precipitation in formulation throughout the period of use of the product.
- compositions according to the invention additionally comprise at least one solubilizer chosen from the group comprising the compounds corresponding to the following INCI designations: caprylyl caprylate/caprate, dibutyl adipate, dicaprylyl carbonate, diisopropyl sebacate, dicaprylyl ether, coco-caprylate , C12-15 alkyl benzoate, propylheptyl caprylate, butylene glycol dicaprylate/dicaprate, dipropylene glycol dibenzoate, neopentyl glycol diheptanoate, triheptanoin, C12-13 alkyl lactate, ethylhexyl benzoate, C12-C15 alkyl lactate, C12-13 alkyl tartrate , tridecyl salicylate , lauryl lactate, diethyl adipate, diisobutyl adipate, diisopropyl adipate, diethylhexy
- Solubilizers capable of being implemented in a composition according to the invention are available on the market from several suppliers.
- the following raw materials can be used in the composition according to the invention: - Several raw materials from the CETIOLTM range marketed by the company BASF, in particular CETIOLTM RLF, CETIOLTM B, CETIOLTM CC, CETIOLTM O, CETIOLTM C5, CETIOLTM AB, CETIOLTM SENSOFT corresponding respectively to the following INCI designations: caprylyl caprylate/caprate, dibutyl adipate, dicaprylyl carbonate, dicaprylyl ether, coco-caprylate, C12-15 alkyl benzoate, propylheptyl caprylate; - DUBTM DIS, DEA, DIBA, ZENOAT marketed by the company STEARINE DUBOIS corresponding respectively to the following INCI designations: diisopropyl sebacate, diethyl adipate, diisobutyl
- the composition according to the invention comprises at least three solubilizers chosen from the group comprising the compounds corresponding to the following INCI designations: caprylyl caprylate/caprate, dibutyl adipate, dicaprylyl carbonate, diisopropyl sebacate, dicaprylyl ether, coco- caprylate, C12-15 alkyl benzoate, propylheptyl caprylate, butylene glycol dicaprylate/dicaprate.
- the composition according to the invention comprises at least the solubilizers corresponding to the following INCI designations: dibutyl adipate, dicaprylyl carbonate and diisopropyl sebacate.
- the composition according to the invention comprises at least the solubilizers corresponding to the following INCI designations: dibutyl adipate, dicaprylyl carbonate, diisopropyl sebacate and propylheptyl caprylate.
- the solubilizers represent between 5% and 80% by mass relative to the total mass of the composition, advantageously between 10% and 70%, preferably between 15% and 60%.
- the composition according to the invention comprises mineral screens (or inorganic mineral filters), which correspond to metal oxides and/or other compounds that are not easily soluble or insoluble in water, in particular oxides titanium (TiO 2 ), zinc (ZnO), iron (Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (for example MnO), aluminum (Al 2 O 3 ), or cerium (Ce 2 O 3 ), or even bismuth trioxide (Bi2O3).
- Inorganic mineral filters can also be surface-treated or encapsulated, in order to give them a hydrophilic, amphiphilic or hydrophobic character.
- composition according to the invention comprises at least one mineral screen chosen from the group comprising the compounds corresponding to the following INCI designations: zinc oxide, titanium dioxide and mixtures thereof.
- zinc oxide corresponds to the raw material Z-COTE ® LSA and titanium dioxide to the raw material T-Lite ® , marketed by the company BASF.
- the lists of UV filters mentioned that can be implemented within the meaning of the present invention are of course given as an indication and not limiting.
- the composition according to the invention has a so-called “SPF” sun protection factor equal to or greater than 20, advantageously equal to or greater than 30, preferably equal to or greater than 40, or even equal to or greater than 50.
- the composition according to the invention comprises a UV-A/UV-B protection ratio equal to or greater than 1/3.
- the composition according to the invention has a critical wavelength ( ⁇ c) greater than 370 nm. This value, which is determined by in vitro methods known to those skilled in the art, corresponds to the wavelength for which the integral of the curve of the absorption spectrum starting at 290 nm reaches 90% of the integral between 290 and 400 nm.
- composition according to the invention may also comprise an SPF "booster”, that is to say an agent for enhancing the sun protection factor, and/or a photo-stabilizer, that is to say an ingredient which makes it possible to increase the SPF or to photo-stabilize the filters, such an ingredient not being considered itself as a sunscreen.
- SPF sun protection factor
- photo-stabilizer that is to say an ingredient which makes it possible to increase the SPF or to photo-stabilize the filters, such an ingredient not being considered itself as a sunscreen.
- - butyloctyl salicylate - butyloctyl salicylate (INCI)
- photostabilizer advantageously representing between 0.01% and 10% by weight relative to the total weight of the composition, even more advantageously between 0.1% and 2%.
- This raw material is, for example, marketed by the company HALLSTAR under the name HallbriteTM BHB; - benzotriazolyl dodecyl p-cresol (INCI), light stabilizer advantageously representing between 0.01% and 10% by weight relative to the total weight of the composition, even more advantageously between 0.1% and 2%.
- This raw material is, for example, marketed by the company BASF under the name of TINOGARDTM TL; - pongamol (INCI), plant molecule absorbing in UV-A, advantageously representing between 0.5 and 2% by weight relative to the total weight of the composition, even more advantageously of the order of 1%.
- the raw material Pongamia Extract marketed by the company GIVAUDAN can be used in the context of the present invention; - ethylhexyl methoxycrylene (INCI), light stabilizer, solubilizer and SPF “booster”, advantageously representing between 1% and 5% by weight relative to the total weight of the composition.
- the SolaStayTM S1 raw material marketed by the company HALLSTAR can be used in the context of the present invention; - a styrene acrylate copolymer (INCI: styrene/acrylate copolymer), preferably representing between 1% and 10% by weight relative to the total weight of the composition according to the invention.
- the raw materials SunSpheresTM H53 and SunSpheresTM PGL Polymer can be used in the context of the present invention; - diethylhexyl syringylidene malonate (INCI), advantageously representing between 1% and 10% by weight relative to the total weight of the composition.
- INCI diethylhexyl syringylidene malonate
- the OXYNETTM ST raw material marketed by the company MERCK, can be used in the context of the present invention; - a water-dispersible polyester, corresponding to the INCI designations polyester-5 (and) Sodium silicoaluminate, advantageously representing between 1% and 10% by weight relative to the total weight of the composition, in particular EASTMANN AQTM38S Polymer marketed by the company SAFIC-ALCAN ; - an acrylate copolymer having a glass transition temperature of -5°C to -15°C as measured by differential scanning calorimetry, said copolymer advantageously representing between 1% and 10% by weight relative to the total weight of the composition.
- the composition according to the invention further comprises other components which may contribute to internal protection by an action which may consist of DNA protection, a reduction in the immunosuppression induced by UV radiation, an anti-radical action or a combined effect of these actions.
- compositions according to the invention against oxidative stress or against the effect of free radicals can be further improved if it additionally comprises one or more antioxidants, easily selected by the skilled in the art, for example from the following list: totarol, magnolol, honokiol, amino acids and their derivatives, peptides (D and/or L-carnosine) and their derivatives (for example anserine, l hypotaurine, taurine), carotenoids, carotenes ( ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (dihydrolipoic acid), aurothioglucose , propylthiouracil and other thiols (thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl,
- antioxidants
- the composition according to the invention also comprises glycyrrhetinic acid, a derivative or a salt of this acid, used as a soothing agent (anti-inflammatory agent) and representing between 0.01% and 2% by weight relative to the total weight of the composition, preferably between 0.1% and 1%.
- the cosmetic and/or dermatological composition comprises at least one, or even all of the following constituents exerting a biological activity in vivo on the cells of the skin, lips, hair and/or mucous membranes subjected to UV-A and/or UV-B radiation, respectively: - an anti-radical agent preserving cellular structures, such as for example vitamin E and/or its fat-soluble or water-soluble derivatives, in particular tocotrienol and/or tocopherol, advantageously representing between 0.001 and 10% by weight relative to the total weight of the composition, even more advantageously between 0.02 and 2%, preferably of the order of 0.04%; - an agent limiting immunosuppression, such as for example vitamin PP, advantageously representing between 0.001 and 1% by weight relative to the total weight of the composition, even more advantageously from 0.01% to 0.3%; - a protective agent for the p53 protein, such as for example epigallocatechin gallate (EGCG), advantageously representing between 0.001 and 0.1%
- EGCG epigalloc
- composition according to the invention may also comprise, in addition, peptide extracts of soybeans and/or wheat, such as those described in document EP 2059230.
- the peptide extracts which come from soybeans and wheat , are derived from an enzymatic hydrolysis of said seeds via peptidases which make it possible to recover peptides with an average size of 700 Daltons.
- the soy peptide extract is the extract identified under CAS number 68607-88-5, as well as the extract wheat peptide is the extract identified under CAS number 70084-87-6.
- Wheat and soy extracts may respectively correspond to the following INCI designations: Hydrolyzed wheat protein and Hydrolyzed soy protein.
- the peptide extracts of soybean and/or wheat are used together, for example in a weight ratio respectively comprised between 80/20 and 20/80, advantageously comprised between 70/30 and 30/70, of preference equal to 60/40.
- the soybean and/or wheat peptide extracts are free of synthetic GHK tripeptides (glycyl-histidyl-lysine; INCI: Tripeptide-1).
- GHK tripeptides GHK tripeptides
- the peptide extracts of soya and/or wheat representing from 0.01 to 20% by weight relative to the total weight of the composition, advantageously from 0.1% to 10%, even more advantageously from 0.2% to 0.7%.
- the composition according to the invention comprises, in accordance with the teachings of document FR 2865398, the combination of at least one amino acid chosen from the group consisting of ectoine, creatine, ergothioneine and / or carnosine, or their physiologically acceptable salts, and mannitol or a mannitol derivative.
- the composition according to the invention comprises, in a physiologically acceptable medium, the amino acid or one of its salts, alone or as a mixture in proportions of between 0.001% and 10% by weight relative to the total weight of the composition, and preferably between 0.01% and 5%.
- composition according to the present invention preferably comprises, in a physiologically acceptable medium, mannitol or one of its derivatives, in proportions of between 0.01% and 30% by weight relative to the total weight of the composition, advantageously between 0.1% and 10%.
- the composition according to the invention comprises ectoin and mannitol.
- the composition according to the invention comprises one or more other tanning or self-tanning agents. It can be a self-tanner which reacts with the amino acids of the skin according to a Maillard reaction or via a Michael addition, or else a promoter of melanogenesis or a propigmenting compound which promotes tanning natural to the skin.
- Such a tanning or self-tanning agent is preferably present in the composition in an amount ranging from 0.01% to 20% by weight relative to the total weight of the composition, advantageously from 0.5% to 15%, even more advantageously from 1 % at 8%.
- Self-tanning substances can be 1,3-dihydroxyacetone (DHA), glycerolaldehyde, hydroxymethylglyoxal, ⁇ -dialdehyde, erythrulose, 6-aldo-D-fructose, ninhydrin, 5-hydroxy-1 ,4-naphthoquinone (juglone), 2-hydroxy-1,4-naphthoquinone (lawsone), or their combination.
- DHA 1,3-dihydroxyacetone
- glycerolaldehyde glycerolaldehyde
- hydroxymethylglyoxal ⁇ -dialdehyde
- 6-aldo-D-fructose ninhydr
- Propigmenting substances can be melanocyte-stimulating hormone ( ⁇ -MSH), ⁇ -MSH peptide analogues, endothelin-1 receptor agonists, opioid ⁇ receptor agonists, cAMP, tyrosinase stimulating agents.
- the composition according to the invention further comprises, as a self-tanner, a combination of dihydroxy methylchromonyl palmitate and/or dimethylmethoxy chromanol, as well as a lipophilic form of tyrosine. This combination of active ingredients effectively stimulates tanning.
- Dihydroxy methylchromonyl palmitate (CAS number: 1387636-35-2) corresponds, for example, to the cosmetic ingredient marketed by the company MERCK under the name RonaCareTM Bronzyl.
- Dimethylmethoxy chromanol (CAS number: 83923-51-7) corresponds, for example, to the cosmetic ingredient marketed by the company LIPOTEC SA under the name lipochromone-6.
- dihydroxy methylchromonyl palmitate or dimethylmethoxy chromanol is included in the composition according to the invention in the amount of 0.01% to 10% by weight relative to the total weight of the composition, advantageously from 0.05 % to 10%, even more advantageously from 0.1% to 5%, more particularly from 0.1% to 0.5%.
- the lipophilic form of tyrosine is a tyrosine-based ingredient and has a more pronounced lipophilic nature than tyrosine.
- the lipophilic form of tyrosine may in particular correspond to oleoyl tyrosine (CAS number: 147732-57-8), which is found, for example, in the liquid cosmetic ingredient TYR-OL, marketed by the company SEDERMA, and which comprises approximately 50% by weight of oleoyl tyrosine in butylene glycol (approximately 30%+approximately 20% oleic acid), or else in the liquid cosmetic ingredient TYR-EXCEL, marketed by the company SEDERMA, which comprises approximately 50 % by weight of oleoyl tyrosine, approximately 20% by weight of oleic acid (CAS No: 112-80-1) and approximately 30% by weight of Luffa cylindrica oil (sponge gourd seed oil; CAS: 1242417
- the lipophilic form of tyrosine corresponds to a vegetable oil in which the tyrosine has been formulated.
- the vegetable oil is oleic sunflower oil, in particular deodorized.
- the raw material OLEOACTIVE TYROSINE BASE HELIANTHUS ANNUS marketed by the company OLEOS, and corresponding to the INCI designations Helianthus annuus seed oil (and) tyrosine (and) glyceryl stearate, can be used in the context of the present invention.
- the lipophilic form of tyrosine such as in cosmetic ingredients based on oleoyl-tyrosine (advantageously at 50% by weight) or tyrosine formulated in vegetable oil, represents between 0.1% and 10% by weight relative to the total weight of the composition, advantageously between 1 and 3%, even more advantageously between 1% and 1.5%.
- composition according to the invention may also comprise active agents having depigmenting properties, such as for example: - lysine azeilate, or other derivatives or salts of azelaic acid; - andrographolide, in particular the extract of Andrographis paniculata corresponding to the INCI designation Andrographis paniculata leaf extract; - native ascorbic acid (vitamin C) or its derivatives, in particular the derivatives corresponding to the INCI Ascorbyl Glucoside, Ethyl ascorbic acid, Ascorbyl methylsilanol pectinate, Sodium ascorbyl phosphate and Ascorbyl tetraisopalmitate, advantageously ascorbyl glucoside; - arbutin or a plant extract containing it, in particular bearberry extract corresponding to the INCI designation Arctostaphylos uva-ursi leaf extract; - glabridin or a plant extract containing it, in particular liquorice extracts corresponding to the INCI designation
- composition according to the invention may also comprise active agents having healing properties such as, for example, an antimicrobial agent chosen from the active agents corresponding to the following INCI designations: copper sulphate, zinc sulphate, sodium hyaluronate, Vitis vinifera (grape) vine extract and mixtures thereof. .
- active agents having healing properties such as, for example, an antimicrobial agent chosen from the active agents corresponding to the following INCI designations: copper sulphate, zinc sulphate, sodium hyaluronate, Vitis vinifera (grape) vine extract and mixtures thereof.
- composition according to the invention may comprise an antimicrobial agent chosen from the active agents corresponding to the following INCI designations: propyl gallate, dodecyl gallate, Ginkgo biloba leaf extract, bakuchiol, dihydromyricetin, zinc gluconate, salicylic acid and mixtures thereof.
- an antimicrobial agent chosen from the active agents corresponding to the following INCI designations: propyl gallate, dodecyl gallate, Ginkgo biloba leaf extract, bakuchiol, dihydromyricetin, zinc gluconate, salicylic acid and mixtures thereof.
- composition according to the invention may therefore also comprise at least one ingredient chosen from the following list: - an agent capable of filtering visible light, in particular blue light; - an extract of Laminaria ochroleuca, Blidingia minima or Laminaria saccharina seaweed; - an extract of the Zanthoxylum alatum plant; - panthenol; - an extract of cade wood; - a Boldo extract; - an extract of Meadowsweet; - an extract of karanja oil from Pongamia glabra; - linear paraffins; - ATP (adenosine-5 tri-phosphate), Gp4G (diguanosine tetraphosphate) or Ap4A (diadenosine tetraphosphate), - an amino acid chosen from the group consisting of decarboxycarnosine, glutamine and their salts.
- an agent capable of filtering visible light in particular blue light
- composition according to the invention may also comprise adjuvants such as those usually used in the field of cosmetics, such as preservatives, antioxidants, complexing agents, solvents, perfumes, fillers, bactericides, electrolytes, odor absorbers, dyestuffs or even lipid vesicles.
- adjuvants such as those usually used in the field of cosmetics, such as preservatives, antioxidants, complexing agents, solvents, perfumes, fillers, bactericides, electrolytes, odor absorbers, dyestuffs or even lipid vesicles.
- the choice of these adjuvants, as well as their concentrations, must be determined so that they do not modify the properties and the advantages sought for the composition of the present invention.
- the composition of the invention is for topical application and more particularly for application to the skin, lips, hair and/or mucous membranes.
- compositions of the invention are in particular intended for the protection of the skin and/or appendages, in particular the mucous membranes, the lips and the hair, against UV radiation.
- the composition of the invention can be in all the dosage forms normally used in the cosmetic and dermatological fields, such as, for example, but in a non-limiting way, in the form of an optionally gelled aqueous solution, of a dispersion of the type lotion, of an O/W emulsion or vice versa W/O, more or less fluid, or of a multiple emulsion such as for example a triple emulsion (W/O/W or O/W/O), or even under the form of a vesicular dispersion of the ionic (liposomes) and/or non-ionic type, of a two-phase composition devoid of emulsifiers and gelling agents whose immiscible phases separate during storage, of foam, of stick, of anhydrous oil, spray or mist.
- the composition according to the invention is a W/O emulsion.
- the W/O emulsions according to the invention comprise PEG-30 dipolyhydroxystearate (INCI), or polyglyceryl-4 diisostearate/polyhydroxystearate/sebacate as emulsifiers. These raw materials are respectively available from CRODA under the trade name of Cithrol DPHS and from EVONIK under the name of Isolan GPS.
- the composition according to the invention is an O/W emulsion.
- the O/W emulsions according to the invention comprise an emulsifier chosen from the following group of compounds identified by their INCI designation: sodium stearoyl glutamate, potassium cetyl phosphate, glyceryl stearate/PEG-100 stearate and C20- 22 alkyl phosphate/C20-C22 alkyl alcohols, tribehenin PEG-20 esters, C14-C22 alcohols/ C12-20 alkyl glucoside, cetearyl alcohol/coco-glucoside, polyglyceryl-6 stearate, polyglyceryl-6 behenate and mixtures thereof.
- emulsifier chosen from the following group of compounds identified by their INCI designation: sodium stearoyl glutamate, potassium cetyl phosphate, glyceryl stearate/PEG-100 stearate and C20- 22 alkyl phosphate/C20-C22 alkyl alcohols, tribehenin PEG-20 esters, C14-C22 alcohol
- the raw materials EMULGIN SG (INCI: sodium stearoyl glutamate; supplier: BASF); EMULIUM 22 (INCI: tribehenin PEG-20 esters; supplier GATTEFOSSE); SENSANOV WR (INCI: C20-22 alkyl phosphate/C20-C22 alkyl alcohols; supplier: SEPPIC); MONTANOV L (INCI: C14-C22 alcohols/ C12-20 alkyl glucoside), AMPHISOL K (INCI: potassium cetyl phosphate; supplier: DSM), MONTANOV 82 (INCI: cetearyl alcohol/coco-glucoside; supplier: SEPPIC) TEGOTM Care PBS 6 MB (INCI: polyglyceryl-6 stearate & polyglyceryl-6 behenate; supplier : EVONIK) can be used in the compositions according to the invention.
- the invention relates to a composition as described above for its use for protection against ultraviolet solar radiation, in particular of wavelength between 100 and 400 nm.
- the invention relates to a composition comprising: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; -at least one UVB organic filter or a broad-spectrum organic filter absorbing in both UVB and UVA; at least one UVA organic filter; for its use to protect the skin, the mucous
- the composition according to the invention is used to filter UV radiation between 280 and 400 nm, in particular between 300 and 380 nm.
- the invention relates to a composition comprising: - at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; - at least two organic filters chosen from UVB organic filters and/or broad-spectrum organic filters absorbing both UVB and UVA rays; -at least one organic UVA screening agent,
- the invention relates to the use: - of at least one MAA as defined above, in particular chosen from the group consisting of the corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as possibly the compound corresponding to CAS number 2699128-33-9; - at least two organic filters chosen from organic UVB filters and/or broad-spectrum organic filters absorbing both UVB and UVA rays; with -at least one UVA organic filter; for its use for the preparation of a cosmetic composition.
- the invention also relates to a cosmetic treatment process consisting in applying to the skin and to the appendages a composition
- a composition comprising: at least one MAA as defined above, in particular chosen from the group consisting of the molecules corresponding to the INCI designations methoxyphenylimino dimethylcyclohexene glycine, caprylyloxyphenylamino dimethyltetrahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylhexahydro benzothiazine carboxylic acid, methoxyphenylimino dimethylcyclohexenyl ethyl glycinate, as well as optionally the compound corresponding to CAS number 2699128-33-9; - at least two organic filters chosen from organic UVB filters and/or broad-spectrum organic filters absorbing both UVB and UVA rays; -at least one organic UVA filter.
- V-1 Aim of the study The aim of the study was the development of compositions with a so-called high sun protection factor SPF , that is to say with an SPF>20, incorporating organic UV filters and the MAAs according to the invention.
- V-2 Materials and methods An in vitro method for measuring the sun protection factor was used. A first measurement of UV absorption is carried out on a plate (plate molded in PMMA or sandblasted plate SB6, Helioscreen) covered with 15 ⁇ l of glycerine (white), this thus makes it possible to overcome the absorption of the support. For the fle1 and fle 2 formulas, the measurements were carried out using HD6 molded plates, according to the following protocol.
- the product studied is sampled and deposited in 16 spots on the HD6 molded plate in PMMA from Helioscreen (5*5cm).
- the quantity weighed is 32.5 mg, which corresponds to a concentration of 1.3 mg/cm2.
- the sample is spread uniformly using a spreader robot (HD-SPREADMASTER-Helioscreen).
- the plate is then placed in the dark at room temperature for at least 15 min.
- the plate is introduced into the measurement enclosure of the Labsphere UV 2000 S spectrophotometer, to perform UV absorption measurements between 290 and 400 nm. Note that a measurement actually corresponds to the average of 9 measurements (9 points of the PMMA plate are measured).
- the protocol is identical but SB6 sandblasted plates were used.
- Table 4 Comparative Formulas Containing Broad Spectrum and UVA Filters
- Table 6 Comparative formulas containing UVB and UVA IV-3 filters Results and discussion The SPF (sun protection factor) conferred by the different filters was measured: [Table 7] Table 7: SPF measurements of fle 1 and fle 2 [Table 8] Table 8: SPF measurements from fle 3 to fle 7 In the case of the tests relating to broad spectrum filters + UVA filter, a very low SPF was obtained for formula 1 (fle 1) containing an MAA according to the invention (INCI: methoxyphenylimino dimethylcyclohexene glycine), a UVA filter and a broad spectrum filter.
- an MAA according to the invention
- the combinations of filters and MAA according to the invention make it possible to obtain products characterized by a good protection index (SPF > 20), while limiting the introduction of organic filters into the formulas thanks to the sun protection amplifier action of MAAs.
- the present invention makes it possible to reduce the quantity and concentration of organic screening agents required in a sunscreen product, while maintaining a high sun protection factor, that is to say greater than 20.
- the use of MAAs as anti-UV agent, in combination with organic filters, is an eco-compatible solution, eco-responsible for the environment and safe for humans.
- OMC Octyl- Methoxycinnamate
- UV Ultraviolet
- the UV-absorber benzophenone-4 alters transcripts of genes involved in hormonal pathways in zebrafish (Danio rerio) eleuthero-embryos and adult males. Toxicol. Appl. Pharmacol.250:137–46 (2011).
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Abstract
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Priority Applications (6)
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BR112023025482A BR112023025482A2 (pt) | 2021-07-08 | 2022-07-07 | Composição |
CA3222853A CA3222853A1 (fr) | 2021-07-08 | 2022-07-07 | Composition cosmetique solaire contenant des acides amines analogues de la mycosporine |
JP2023577991A JP2024524147A (ja) | 2021-07-08 | 2022-07-07 | マイコスポリン様アミノ酸を含む日焼け防止化粧用組成物 |
EP22751136.7A EP4366686A1 (fr) | 2021-07-08 | 2022-07-07 | Composition cosmetique solaire contenant des acides amines analogues de la mycosporine |
CN202280043676.1A CN117529303A (zh) | 2021-07-08 | 2022-07-07 | 含有类菌孢素氨基酸的防晒化妆品组合物 |
KR1020237043361A KR20240032736A (ko) | 2021-07-08 | 2022-07-07 | 마이코스포린 유사 아미노산을 함유하는 항-일광 화장료 조성물 |
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FR2107441A FR3124945A1 (fr) | 2021-07-08 | 2021-07-08 | Composition cosmetique solaire contenant des acides amines analogues de la mycosporine |
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EP (1) | EP4366686A1 (fr) |
JP (1) | JP2024524147A (fr) |
KR (1) | KR20240032736A (fr) |
CN (1) | CN117529303A (fr) |
BR (1) | BR112023025482A2 (fr) |
CA (1) | CA3222853A1 (fr) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024027927A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition avec fps et photoprotection contre les uva améliorés |
WO2024027929A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition avec résistance à l'eau améliorée |
WO2024027926A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition comprenant un stabilisant de filtre uv |
WO2024027930A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Compositions comprenant un agent renforçateur antimicrobien |
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-
2021
- 2021-07-08 FR FR2107441A patent/FR3124945A1/fr active Pending
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2022
- 2022-07-07 KR KR1020237043361A patent/KR20240032736A/ko unknown
- 2022-07-07 CA CA3222853A patent/CA3222853A1/fr active Pending
- 2022-07-07 CN CN202280043676.1A patent/CN117529303A/zh active Pending
- 2022-07-07 EP EP22751136.7A patent/EP4366686A1/fr active Pending
- 2022-07-07 JP JP2023577991A patent/JP2024524147A/ja active Pending
- 2022-07-07 WO PCT/FR2022/051365 patent/WO2023281224A1/fr active Application Filing
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2024027927A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition avec fps et photoprotection contre les uva améliorés |
WO2024027929A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition avec résistance à l'eau améliorée |
WO2024027926A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition comprenant un stabilisant de filtre uv |
WO2024027930A1 (fr) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Compositions comprenant un agent renforçateur antimicrobien |
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JP2024524147A (ja) | 2024-07-05 |
CN117529303A (zh) | 2024-02-06 |
EP4366686A1 (fr) | 2024-05-15 |
KR20240032736A (ko) | 2024-03-12 |
CA3222853A1 (fr) | 2023-01-12 |
BR112023025482A2 (pt) | 2024-02-27 |
FR3124945A1 (fr) | 2023-01-13 |
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