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    • 专利摘要:
    The invention relates to a composition in the form of a nano- or microemulsion, comprising: a) hesperetin; b) at least one fatty acid ester and (poly) glycerol; c) at least one polyol; e) at least one oil, f) water. The composition is preferably a cosmetic composition, and may be in the form of a nano- or microemulsion with a transparent or slightly translucent appearance. Application to the care, makeup and / or cleaning of keratin materials, especially the skin.
    公开号:FR3029781A1
    申请号:FR1462329
    申请日:2014-12-12
    公开日:2016-06-17
    发明作者:Vera Lucie Esteves；Chantal Jouy；Celine Derrips
    申请人:LOreal SA；
    IPC主号:
    专利说明:

    [0001] Composition comprising hesperetin, an oil, at least one fatty acid ester and (poly) glycerol, a polyol The subject of the present invention is a composition, in particular a cosmetic composition, comprising hesperetin in the form of a nano- or microemulsion. Hesperetin is an organic compound of the flavanone family, a subgroup of flavonoids. It is found in nature mainly in the form of its heteroside, hesperidin which is present in fruits of the genus Citrus.
    [0002] Hesperetin is an interesting substance as an antioxidant and for the treatment of cutaneous signs of aging. However, this compound, which is in solid form at high temperature and has a high melting point (220 ° C.), is difficult to solubilize, in particular it is poorly soluble in water and glycerol. However, it is necessary for this compound to be formulated in a solubilized form, and in particular at a high content, especially greater than or equal to 0.30% by weight, in order to make the most of its activity, and it is also preferable that its solubilization is maintained over time to avoid any recrystallization phenomenon when storing compositions comprising such a compound. In addition it may be interesting to formulate this compound in oil emulsions in water (O / W), known in the art in the cosmetic or dermatological field. ).
    [0003] These emulsions, which consist of an oily phase (or a lipophilic phase) dispersed in an aqueous phase, have an external aqueous phase and are therefore products which are more pleasant to use because of the sensation of freshness than they provide. However, they have the disadvantage of lack of stability when the amount of oil present is too high. Today, for certain applications, it is advantageous to have a large amount of oils since the oils provide comfort for the skin, nourish it, and can also remove makeup from it when these oils have cleansing properties. In addition, it is advantageous to have fine emulsions, that is to say, emulsions in which the oily phase is in the form of very small droplets, that is to say of droplets of less than 4 pm of size, since these fine emulsions provide a pleasant cosmetic sensation and are generally more stable than coarse emulsions.
    [0004] These emulsions can be prepared, in particular, by the phase inversion temperature technique (PIT emulsions), in which the average size of the globules constituting the oily phase is within given limits, namely between 0.1 and 4 pm (100 to 4000 nm). The principle of emulsification by phase inversion temperature (or PIT) is, in theoretical terms, known to those skilled in the art; it was described in 1968 by K. Shinoda (J. Chem Soc Jpn., 1968, 89, 435). It has been demonstrated that this emulsification technique makes it possible to obtain stable fine emulsions (K. Shinoda and H. Saito, J. Colloid Interface Sci., 1969, 30, 258). This technology has been applied in cosmetics since 1972 by Mitsui et al. ("Application of the phase-inversion-temperature method to the emulsification of cosmetics", T. Mitsui, Y. Machida and F. Harusawa, American, Cosmet Perfum., 1972, 87, 33). The principle of this technique is as follows: an HIE emulsion (introduction of the aqueous phase into the oily phase) is prepared at a temperature which should be higher than the phase inversion temperature of the system, that is, that is, the temperature at which the balance between the hydrophilic and lipophilic properties of the emulsifier (s) used is obtained; at a higher temperature, ie greater than the phase inversion temperature (> PIT), the emulsion is of the water-in-oil type and, when it is cooled, this emulsion is reversed at the phase inversion temperature so as to become an oil-in-water emulsion, having previously passed through a microemulsion state. This process makes it easy to obtain emulsions with a diameter generally less than 4 μm. The conventionally used oil-in-water emulsifier surfactants have an HLB (HLB = hydrophilic-lipophilic balance) in the range of 8 to 18.
    [0005] These emulsifiers, because of their amphiphilic structure, are located at the oily phase / aqueous phase interface, and thus stabilize the dispersed oil droplets. However, it is difficult to produce fine HIE emulsions containing a large amount of oily phase, since such emulsions have a tendency to destabilize, this destabilization leading to coalescence and separation of the aqueous and oily phases with release of the oil phase. oil. In order to improve the stability of these emulsions, the concentration of emulsifiers can be increased; however, a high concentration of emulsifiers can lead to a rough, tacky or tacky feel, and to skin, eye and scalp safety issues.
    [0006] In particular, a fine emulsion such as a nano- or microemulsion O / W is particularly interesting in cosmetics because of its transparent or slightly translucent appearance.
    [0007] For example, JP-A-H09-110635 discloses a fine emulsion which is formed using a combination of polyglyceryl fatty acid ester as a surfactant and a C10-C22 fatty 2-hydroxy acid. In addition, JP-A-H11-71256 discloses a fine emulsion which is formed using a combination of polyglyceryl fatty acid ester and betaine.
    [0008] However, when certain types of nonionic surfactant are used to prepare fine emulsions, the transparent or slightly translucent appearance of the emulsion as well as the stability of the emulsion are not sufficient.
    [0009] The object of the present invention is precisely to propose a new galenetic formulation of hesperetin making it possible to overcome the above-mentioned drawbacks, and thus to incorporate this compound in a solubilized and durable form over time, especially when this compound is present at a high content (such as a content greater than or equal to 0.30% by weight relative to the total weight of the composition), and especially in a composition in the form of a nano- or microemulsion having a transparent or slightly translucent appearance, preferably transparent. This new galenic formulation of hesperetin makes it possible in particular to improve the efficacy of the active ingredient for the treatment of keratin materials such as the skin.
    [0010] After extensive research, the inventors have, in particular, unexpectedly discovered that it is possible to produce such a composition in which the hesperetin is solubilized and its recrystallization avoided, especially after storage for 2 months at room temperature. (25 ° C), this composition being stable in the form of a microemulsion nanoou, having in particular an aspect of the transparent or slightly translucent emulsion, preferably transparent. Accordingly, the present invention relates to a composition, preferably a cosmetic, in the form of a nano- or microemulsion, comprising; a) hesperetin: b) at least one fatty acid ester and (poly) glycerol; c) at least one polyol; d) at least one oil; 3029781 4 e) water. More particularly, the present invention relates to a composition, in the form of na-no- or microemulsion, comprising; A) hesperetin: b) at least one fatty acid ester of (poly) glycerol formed of at least one acid comprising a saturated linear alkyl chain containing from 12 to 22 carbon atoms and from 1 to 12 glycerol units; c) at least one polyol; D) at least one oil; e) water. More particularly, the present invention relates to a composition, in the form of na-no- or microemulsion, comprising; A) hesperetin: b) at least two fatty acid esters of (poly) glycerol formed of at least one acid comprising a saturated linear alkyl chain containing from 12 to 22 carbon atoms and from 1 to 12 glycerol patterns different from each other; c) at least one polyol; D) at least one oil; e) water. Since the cosmetic composition according to the present invention can have a transparent or slightly translucent appearance, the composition can be used preferably for lotions and the like. In addition, the cosmetic composition according to the present invention can produce a pleasant texture and provides moisturizing properties as well as increased flexibility. In addition, if the dispersed phase is an oily phase and comprises one or more lipophilic or even amphiphilic active components, the oily dispersed phase can function as a carrier of the active substance and accelerate the penetration of the active components into the skin. , or can distribute the active components on the skin. Hereinafter, the composition, preferably cosmetic, according to the present invention is described in more detail.
    [0011] The composition of the invention may be a cosmetic composition (either intended for cosmetic use) or dermatological. Preferably, according to the invention, the composition is a cosmetic composition and even more preferentially a cosmetic composition for topical application.
    [0012] The term "cosmetic composition" is understood to mean a substance or a preparation intended to be placed in contact with the various superficial parts of the human body, in particular the epidermis, the hair and hair systems, the nails, the lips, the oral mucosa, in view, exclusively or mainly, to clean, embellish, perfume, modify their appearance, protect them, maintain them in good condition or correct body odors. The composition according to the invention comprises hesperetin.
    [0013] Hesperetin is a compound of chemical structure: HO H O Hesperetin is also named - 3 ', 5,7-Trihydroxy-4'-methoxyflavanone, or (S) -2,3-dihydro-5,7 dihydroxy-2- (3-hydroxy-4-methoxyphenyl) -4H-1-benzopyran-4-one (CAS no .: 520-33-2). Hesperetin is especially available under the trade name HESPERETIN PURIFIED® from Ferrer Grupo-Exquim (Ferrer), or under the name FMLT HespeSphere 1.0® from Biospectrum, Inc., or under the name GFX. ® of the company Industrial Research Limited, or under the name Jeju Citrus Aglyconoid Liposome® of the company. The hesperetin (a) may be present in the composition according to the invention, in a content ranging from 0.05% to 5% by weight, relative to the total weight of the composition, preferably from 0, 20% to 2% by weight, preferably ranging from 0.30% to 1.5% by weight, and particularly ranging from 0.40% to 1% by weight.
    [0014] Preferably, hesperetin (a) is present in the composition according to the invention at a content greater than or equal to 0.30% by weight relative to the total weight of the composition, preferably at a content greater than or equal to to 0.40% by weight relative to the total weight of the composition, and more preferably to a content greater than or equal to 0.50% by weight relative to the total weight of the composition. Fatty acid ester (s) and (poly) glycerol (b) The composition according to the present invention comprises at least one fatty acid ester and (poly) glycerol. In a particular embodiment, the composition according to the present invention comprises at least a first fatty acid ester and (poly) glycerol and at least a second fatty acid ester and (poly) glycerol different from one of the other. The fatty acid and glycerol or polyglycerol esters used in the context of the present invention are nonionic surfactants which are solid at a temperature of less than or equal to 45 ° C.
    [0015] The compositions according to the invention comprise at least one fatty acid ester of glycerol or polyglycerol, optionally polyoxyalkylenated. The (poly) glycerol esters according to the invention are glycerol esters (or mono-glyceryl esters) or polyglycerol esters (or polyglyceryl esters) such as diglyceryl (or diglycerol) esters. According to one embodiment, the (poly) glycerol ester according to the invention results from the esterification of at least one fatty acid, saturated or unsaturated, and a (poly) glycerol. In the context of the present invention, the term "(poly) glycerol" refers to glycerol or glyceryl polymers. When it is a polymer, polyglycerol is generally a linear sequence of 1 to 22, preferably 1 to 12 glycerol units. In the context of the present invention, the term "polyoxyalkylenated (poly) glycerol" corresponds to polyoxyalkylenated ethers of glycerol (or polyglycerol) and preferably polyoxyethylenated ethers (or polyethylene glycol).
    [0016] The esters more particularly considered according to the present invention are esters resulting from the esterification of poly (glycerol) and carboxylic acid (s) C4-C36, preferably C4-C18, and more particularly C6 to C12, especially C7 to C10.
    [0017] In general, they are derived from the esterification of at least one hydroxyl function of a poly (glycerol) with a carboxylic acid C4-C36, preferably C4-C18, and more particularly C6-C6. C12, especially C7 to 010. According to a particular embodiment, the esters that are suitable for the present invention can be derived from the esterification of a poly (glycerol) with one or more identical or different carboxylic acids. It may be a hydroxylated mono-ester, a hydroxylated di-ester, a hydroxylated tri-ester, or a mixture thereof. A preferred cosmetic composition according to the invention comprises a (po- ly) glycerol ester selected from the group consisting of glycerol and glycerol polymers. According to one embodiment, the fatty acid is a linear or branched, saturated or unsaturated carboxylic acid comprising from 4 to 36 carbon atoms, and preferably from 4 to 18 carbon atoms, and more particularly from 6 to 12 carbon atoms. carbon atoms, especially from 7 to 10 carbon atoms. Preferably, the fatty acid is a saturated monocarboxylic fatty acid comprising from 8 to 18 carbon atoms. The carboxylic acid may be linear or branched, saturated or unsaturated. Advantageously, it is a linear monocarboxylic acid.
    [0018] Illustrative examples of monocarboxylic acid suitable for the invention include butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, hep-tadecanoic acid, hexadecanoic acid and pentadecanoic acid and octadecanoic acid; (stearic acid). As representative of the branched acids, mention may be made more particularly of isobutanoic acid, isopentanoic acid, pivalic acid, isohexanoic acid, isoheptanoic acid, isooctanoic acid and dimethyloctanoic acid. isononanoic acid, isodecanoic acid, isoundecanoic acid, isododecanoic acid, isotridecanoic acid, isotetradecanoic acid, isopentadecanoic acid, isohexadecanoic acid, 2-ethylhexanoic acid, acid 2-butyloctanoic acid and 2-hexildecanoic acid. Also suitable for the present invention are hydroxy acids such as 2-hydroxybutanoic acid, 2-hydropentanoic acid, 2-hydroxyhexanoic acid, 2-hydroxyheptanoic acid, 2-hydroxyoctanoic acid, acid 2 2-hydroxydecanoic acid, 2-hydroxyundecanoic acid, 2-hydroxydodecanoic acid, 2-hydroxytridecanoic acid, 2-hydroxytetradecanoic acid and 2-hydroxyhexadecandic acid. It is more particularly a non-hydroxyl acid C7 to 010 and more particularly heptanoic acid, caprylic acid and capric acid.
    [0019] In the context of the present invention, mention may also be made of oxyalkylenated glycerol esters and in particular polyoxyethylenated derivatives of glyceryl esters of fatty acids and of their hydrogenated derivatives. These oxyalkylenated glycerol esters may be chosen, for example, from glyceryl esters of hydrogenated and oxyethylenated fatty acids, such as PEG-200 hydrogenated glyceryl palmate sold under the name Rewoderm LI-S 80 by the company Goldschmidt; oxyethylenated glyceryl cocoates such as PEG-7 glyceryl cocoate sold under the name Tegosoft GC by the company Goldschmidt, and PEG-30 glyceryl cocoate sold under the name Rewoderm LI-63 by the company Goldschmidt; and their mixtures.
    [0020] Esters selected from the group consisting of mono- and / or di-glyceryl caprylate, mono- and / or di-glyceryl heptanoate, monoet / di-glyceryl caprylate, propylene glycol caprylate, heptanoate, are particularly suitable for the invention. propylene glycol and mixtures thereof. It is more particularly monoglyceryl caprylate (also called glycerol caprylate) and mixtures thereof. According to one embodiment, the (poly) glycerol ester according to the invention is selected from the group consisting of glyceryl caprylate, poly (I) -alkyl caprylate, polyglyceryl-2 caprate, polyglyceryl-3 caprate, polyglyceryl-4-caprate, glyceryl laurate, polyglyceryl-2 laurate, polyglyceryl-5 laurate, polyglycerol laurate-10, glyceryl myristate, glyceryl stearate, undecylenate of glyceryl, caprylate / glyceryl caprate, PG-4 laurate, PG-5 dilaurate, PG-5 oleate, PG-5 dioleate, PG-6 tricaprylate, PG-5 myristate, PG trimyristate -5, PG-5 stearate, PG-5 isostearate, PG-5 trioleate, PG-6 caprylate, and PG-6 tricaprilate, decaflyceryl monostearate, distearate, tristearate, and pentastearate (CTFA names : polyglyceryl-10 stearate, polyglyceryl-10-distearate, polyglyceryl-10-tristearate, polyglyceryl-10-pentastearate) The products marketed under the respective names Nikkol Decaglyn 1S, 2S, 3S and 5S by the company Nikko, and the diglyceryl monostearate (CTFA name: polyglyceryl-2 stearate), such as the product sold by Nikko company under the name Nikkol DGMS. and their mixtures.
    [0021] According to a particular embodiment, the composition according to the present invention comprises; at least one first fatty acid ester of (poly) glycerol formed from at least one acid comprising a saturated linear alkyl chain containing from 12 to 22 carbon atoms and from 1 to 12 glycerol units; at least one second fatty acid ester of (poly) glycerol formed from at least one acid comprising a saturated linear alkyl chain containing from 12 to 22 carbon atoms and from 1 to 12 glycerol units.
    [0022] In a preferred embodiment, the composition according to the invention comprises; a first fatty acid ester and (poly) glycerol which is chosen from a fatty acid ester of (poly) glycerol formed from at least one acid comprising a saturated linear alkyl chain containing from 12 to 18 atoms of carbon and 3 to 6 glycerol units, and / or - a second fatty acid ester and (poly) glycerol which is selected from a fatty acid ester and (poly) glycerol formed of at least one acid comprising a saturated linear alkyl chain containing from 12 to 18 carbon atoms and from 1 to 4 glycerol units. In a particularly advantageous manner, the composition according to the invention comprises; as the first fatty acid ester and (poly) glycerol, polyglyceryl-5 laurate, and / or - as the second fatty acid ester and poly (poly) is polygleryl-laurate. polyglyceryl5 or laurate of PG-5 is available under the trade name LAURATE SUNSOFT A-121E0 by the company Taiyo Kagaku.
    [0023] Polygleryl-2 laurate or PG-5 laurate is available under the trade name SUNSOFT Q-12D-C® from Taiyo Kagaku.
    [0024] In the compositions according to the invention the total amount of the fatty acid ester (s) and (poly) glycerol (b) may be present in a content of from 0.50% to 20% by weight, of preferably from 2% to 15% by weight, and more preferably from 6% to 12% by weight, based on the total weight of the composition.
    [0025] Polyol (c) The composition according to the present invention comprises at least one polyol.
    [0026] By polyol according to the invention is meant a hydrocarbon chain comprising at least 2 carbon atoms, preferably from 2 to 50 carbon atoms, preferably from 4 to 20 carbon atoms, preferably having from 2 to 10 atoms. carbon, and preferably having from 2 to 6 carbon atoms, and bearing at least two hydroxyl groups. The polyols used in the present invention may have a weight average molecular weight of less than or equal to 1000, preferably between 90 and 500. The polyol may be a natural or synthetic polyol. The polyol may have a linear, branched or cyclic molecular structure. The polyol may be selected from glycerin and derivatives thereof, and glycols and derivatives thereof. The polyol may be selected from the group consisting of glycerin, diglycerin, polyglycerin, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, propanediol, 1,5-pentanediol, polyethyleneglycol, especially having 5 to 50 ethylene oxide groups, and sugars such as sorbitol, and a mixture thereof. More particularly, the polyol may be selected from the group consisting of dipropylene glycol, butylene glycol, and a mixture thereof. The said polyol (s) may be present in a content ranging from 2% to 50% by weight, relative to the total weight of the composition, preferably ranging from 5% to 40% by weight. weight, and preferably ranging from 20% to 30% by weight.
    [0027] Oil (d) The cosmetic composition according to the present invention comprises at least one oil (d).
    [0028] According to the present invention, an "oil" refers to a compound or fatty substance (se) which is in the form of a liquid at room temperature (25 ° C) at atmospheric pressure (760 mmHg). As oils, those generally used in cosmetics can be used alone or in combinations thereof. These oils may be volatile or non-volatile, preferably non-volatile.
    [0029] The oil may be a non-polar oil such as a hydrocarbon oil, a silicone oil, or the like; a polar oil such as a vegetable or animal oil and an ester oil or an ether oil; or a mixture thereof.
    [0030] It is preferred that the oil (d) be selected from the group consisting of vegetable oils, animal oils, synthetic oils, silicone oils and hydrocarbon oils.
    [0031] Examples of vegetable oils include, for example, linseed oil, camellia oil, macadamia oil, corn oil, castor oil, soybean oil and the like. olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, sunflower oil, almond oil, lemon rapeseed oil, sesame oil, soybean oil, peanut oil, argan oil, apricot kernel oil and mixtures thereof. As examples of animal oils, it may be mentioned, for example, squalene and squalane.
    [0032] As examples of synthetic oils, there may be mentioned alkanes such as isododecane and isohexadecane, fatty esters, fatty ethers, and artificial C 6 -C 22 acid triglycerides. The fatty esters are preferably liquid esters of linear or branched, saturated or unsaturated C 1 -C 26 monohydric acids or polybasic acids and linear or branched, saturated or unsaturated C 1 -C 26 aliphatic polyhydric alcohols or alcohols. the total number of carbon atoms of the fatty esters being greater than or equal to 10. Preferably, for the monoalcohol esters, at least one of the alcohol and the acid is branched. Among monoesters of monoacids and monoalcohols, mention may be made of ethyl palmitate, ethylhexyl palmitate, isopropyl palmitate, dicaprylyl carbonate, alkyl myristates such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isononyl isononanoate, isodecyl neo-pentanoate and isostearyl neopentanoate. Esters of C4-C22 dicarboxylic or tricarboxylic acids and 01022 alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and dihydroxy, trihydroxy, tetrahydroxy or non-carbohydric C4-C26 pentahydroxy alcohols may also be present. used.
    [0033] In particular, mention may be made of: diethyl sebacate; isopropyllauryl sarcosinate; diisopropyl sebacate; bis (2-ethylhexyl) sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; bis (2-ethylhexyl) adipate; diisostearyl adipate; bis (2-ethylhexyl) maleate; triisopropyl citrate; triisocetyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate. As fatty esters, it is possible to use fatty acid esters and diesters of C6-C30 and preferably C12-C22 fatty acids. It is recalled that the term "sugar" refers to hydrocarbon-based compounds containing oxygen containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars can be monosaccharides, oligosaccharides or polysaccharides.
    [0034] Examples of suitable sugars which may be mentioned include sucrose (sucrose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, in particular alkyl derivatives, such as methyl derivatives, for example methylglucose.
    [0035] The sugar fatty acid esters may be chosen, in particular from the group consisting of the esters or mixtures of sugar esters previously described and linear or branched C6-C30 and preferably C12-C22 fatty acids. , saturated or unsaturated. If unsaturated, these compounds may have one to three conjugated or unconjugated double bonds. Esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
    [0036] These esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof, such as, in particular, mixed esters. of oleopalmitate, oleostearate and palmitostearate, as well as pentaerythrityl tetraethylhexanoate. More particularly, monoesters and diesters are used, in particular sucrose, glucose or methylglucose mono-and diol esters, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
    [0037] An example that can be mentioned is the product marketed under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate. As preferred examples of fatty esters, there can be mentioned, for example, diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, sodium octanoate and the like. cetyl, octyldodecyl octanoate, isodecyl neopentanoate, myristyl propionate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl octanoate, 2-ethylhexyl caprylate / caprate, methyl palmitate , ethyl palmitate, isopropyl palmitate, ethylhexyl palmitate, isohexyl laurate, hexyl laurate, isocetyl stearate, isopropyl isostearate, isopropyl myristate , isodecyl oleate, glyceryl tri (2-ethylhexanoate), pentaerythritol tetra (2-ethylhexanoate), 2-ethylhexyl succinate, diethyl sebacate, and mixtures thereof.
    [0038] As examples of artificial triglycerides, mention may be made of, for example, glyceryl tritmyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri (caprate / caprylate) and glyceryl tri (caprate / caprylate / linolenate).
    [0039] As examples of silicone oils, there may be mentioned, for example, linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like; cyclic organopolysiloxanes such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like; and mixtures thereof.
    [0040] Preferably, the silicone oil is selected from liquid polydialkylsiloxanes, particularly liquid polydimethylsiloxanes (PDMSs) and liquid polyorganosiloxanes comprising at least one aryl group.
    [0041] These silicone oils can also be organomodified. The organomodified silicones which can be used according to the present invention are silicone oils as defined above and comprising in their structure one or more organofunctional groups linked via a hydrocarbon-based group.
    [0042] Organopolysiloxanes are defined in more detail in Walter Noll's Chemistry and Technology of Silicones (1968), Academic Press. They can be volatile or non-volatile.
    [0043] Volatile or non-volatile silicone oils, such as volatile or non-volatile polydimethylsiloxanes (PDMS) containing a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane ; polydimethylsiloxanes containing alkyl, alkoxy or phenyl groups which are pendant or at the end of the silicone chain, said groups having from 2 to 24 carbon atoms; phenylsilicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyldimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes may be used. The hydrocarbon-based oils may be chosen from: linear or branched, optionally cyclic, C6-C16 lower alkanes. Examples which may be mentioned include hexane, undecane, dodecane, tridecane, and isoparaffins, for example, isohexadecane, isododecane and isodecane; and linear or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffins, liquid paraffin gel, polydecenes and hydrogenated polyisobutenes such as Parleamil, and squalane.
    [0044] As preferred examples of hydrocarbon oils, there may be mentioned, for example, linear or branched hydrocarbons such as mineral oil (eg, liquid paraffin), paraffin, petrolatum or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosane, and a decene / butene copolymer; and mixtures thereof. It is also preferable that the oil (e) is selected from oils having a molecular weight of less than 600 g / mol.
    [0045] Preferably, the oil (e) is selected from fatty esters having a C1-012 hydrocarbon chain or chains (eg, isopropyl myristate, isopropyl palmitate, isononyl isononanoate, and palmitate). ethylhexyl), hydrocarbon oils (eg, isododecane, isohexadecane, and squalane), branched and / or unsaturated C 12 -C 30 fatty alcohol oils such as octyldodecanol, oleyl alcohol, fatty ethers such as dicaprylyl ether. Particularly preferably, the oil (d) is selected from ethylhexyl palmitate and isopropyl myristate.
    [0046] Ethylhexyl palmitate is available under the trade name ETHYL 2 HEXYL PALMITATE (DUB PO) ® from the company STEARINERIE DUBOIS.
    [0047] The amount in the cosmetic composition according to the present invention of the oil (s) (d) may be present in a content of from 0.50% to 50% by weight, preferably from 1% to 15% by weight. weight, and more preferably from 2% to 5% by weight, based on the total weight of the composition.
    [0048] In a particular embodiment, the (s) fatty acid ester (s) and (poly) glycerol (b) and the oil (s) (d) are present in a composition according to the invention such that defined above, in a mass ratio [total amount of fatty acid ester (s) and (poly) glycerol (b) 15 / oil (s) (d)] which ranges from 0.50 to 10, In a particular embodiment, the fatty acid ester (s) and (poly) glycerol (b) and hesperetin (a) are present in a composition according to claim 1. as defined above, in a mass ratio [total amount of fatty acid ester (s) and (poly) glycerol (b) / hesperetin (a)] which is at least 2, in particular ranging from 2 to 40, and preferably ranging from 5 to 20. According to a preferred embodiment, the (s) esters of fatty acid and (poly) glycerol (b) according to the invention are respectively the laurate of polyglyceryl-5 and po- lyglyceryl-2 laurate, and they are present in the composition according to the invention with hesperetin in a mass ratio [PG-5 + PG-2 / hesperetin] which is at least 2, in particular ranging from 2 to 40, and preferably ranging from 5 to at 20.
    [0049] Water (e) The cosmetic composition according to the present invention comprises water. The amount of water (e) is not limited, and may range from 40 to 99% by weight, preferably from 55 to 95% by weight, and more preferably from 60 to 90% by weight, based on total weight of the composition.
    [0050] The composition according to the present invention may further comprise at least one additional surfactant different from the ester (s) of fatty acid and (poly) glycerol (b) as defined above.
    [0051] The amount of the additional surfactant (s) may be from 0.01% by weight to 20% by weight, preferably 0.10% by weight to 10% by weight, and more preferably 1% by weight. weight at 5% by weight, relative to the total weight of the composition. Thickening agent The cosmetic composition according to the present invention may further comprise at least one thickening agent. The thickening agent may be chosen from organic and inorganic thickeners. The thickening agent is preferably selected from associative thickeners and polysaccharides such as starch and xanthan gum. As used herein, the term "associative thickener" refers to an amphiphilic thickener comprising both hydrophilic and hydrophobic units, for example, comprising at least one C8-C30 fatty chain and at least one hydrophilic unit. The viscosity of the cosmetic composition according to the present invention is not particularly limited. The viscosity can be measured at 25 ° C with viscometers or rheometers preferably having a cone-plane geometry. Preferably, the viscosity of the cosmetic composition according to the present invention may be, for example, from 1 to 2000 Pa.s, and preferably from 1 to 1000 Pa.s at 25 ° C and 1 s-1. The thickener may be present in an amount in the range of from 0.001% to 10% by weight, and preferably from 0.01% to 10% by weight, for example from 0.1% to 5% by weight, relative to the total weight of the composition. [Other components] The cosmetic composition according to the present invention may further comprise an effective amount of other components, previously known in particular in compositions including cosmetic, such as various adjuvants, anti-aging agents, bleaching agents, anti-oily skin agents sequestering agents such as EDTA and etidronic acid, anti-UV agents, preservatives, vitamins or provitamins, for example panthenol, opacifiers, perfumes, plant extracts, cationic polymers etc.
    [0052] Preparation and Properties The cosmetic composition according to the present invention can be prepared by mixing the above essential and optional components according to a conventional method. The conventional method comprises mixing with a high pressure homogenizer (a high energy process). Alternatively, the cosmetic composition may be prepared by a low energy method such as a phase inversion temperature (PIT) method, a phase inversion concentration (PIC), autoemulsification, and the like. Preferably, the cosmetic composition is prepared by a low energy process.
    [0053] In a particular embodiment, the mass ratio between the total amount of the fatty acid ester (s) and (poly) glycerol (b) and the oil (d) in a composition according to the invention as defined above, ranges from 0.50 to 10, preferably from 1 to 5.
    [0054] The cosmetic composition according to the present invention is in the form of a nano- or microemulsion.
    [0055] The "microemulsion" can be defined in two ways, i.e., in a broad sense and in a more restricted sense. Namely, in one case ("micro-emulsion in the narrow sense"), the microemulsion denotes a thermodynamically stable single isotropic liquid phase containing a ternary system having three components comprising an oily component, an aqueous component and a surfactant, and the other case ("broad-spectrum microemulsion"), among the typical thermodynamically unstable emulsion systems, the microemulsion further comprises emulsions having transparent or translucent aspects due to their smaller particle sizes (Satoshi Tomomasa, et al., Oil Chemistry, 37, 11 (1988), 48-53). "Microemulsion" in the present context refers to a "microemulsion in the restricted sense", i.e., a thermodynamically stable single isotropic liquid phase. The microemulsion denotes a state of a microemulsion of the O / W type (oil in water) in which the oil is solubilized by micelles, a W / H type microemulsion (water 3029781 18 in the oil) in which the water is solubilized by inverse micelles, or a bicontinuous microemulsion in which the number of associations of surfactant molecules is brought to be infinite so that the aqueous phase and the oily phase all have two a continuous structure.
    [0056] The microemulsion may have a dispersed phase having a number average diameter of 100 nm or less, preferably 50 nm or less, and more preferably 20 nm or less, as measured by laser particle size.
    [0057] The "nanoemulsion" currently refers to an emulsion characterized by a dispersed phase having a size less than 350 nm, the dispersed phase being stabilized by a ring of the nonionic surfactant (b) which can optionally form a liquid crystal phase of the type lamellar at the disperse phase / continuous phase interface. In the absence of specific opacifiers, the transparency of the nanoemulsions is due to the small size of the dispersed phase, this small size being obtainable thanks to the use of mechanical energy and in particular a high pressure homogenizer. Nanoemulsions can be distinguished from microemulsions by their structure. Specifically, the microemulsions are thermodynamically stable dispersions formed, for example, swollen micelles of nonionic surfactant (b) with the oil (a).
    [0058] In addition, the microemulsions do not require substantial mechanical energy to be prepared. The microemulsion may have a dispersed phase having a number average diameter of 300 nm or less, preferably 200 nm or less, and more preferably 100 nm or less, as measured by laser particle size. The cosmetic composition according to the present invention may be in the form of a na-NO- or micro-O / W emulsion, a W / O nanomed or microemulsion or a bicontinuous emulsion. It is preferred that the cosmetic composition according to the present invention is in the form of a nano- or micro-O / W emulsion. It is preferable that the cosmetic composition according to the present invention is in the form of an O / W emulsion.
    [0059] The average size of the oily phase droplets is measured concentrated by dynamic light scattering (DDL) with a VASCO granulometer. These measurements are performed on the undiluted emulsion.
    [0060] The average number size (μm) of the oil phase droplets of the composition of the invention is less than 300 nm and preferably 10 nm to 150 nm, and more preferably 20 nm to 100 nm.
    [0061] The cosmetic composition according to the present invention may have a transparent or slightly translucent appearance, preferably a transparent appearance. Transparency can be measured by measuring the transmittance with an absorption spectrometer in the visible region (for example, transparency is measured with a Hach 2100Q portable turbidimeter at 25 ° C. The portable turbidimeter uses the nephelometric measurement principle The nephelometric turbidity measurement depends on the detection of the light dispersed by the particles in suspension in the liquid The unit of measure is the NTU A round cell 60 x 25 cm made of borosilicate glass with a cap is used The amount of sample required is 15 ml, the measuring range is 0-1000 NTU, the samples are measured undiluted and the cosmetic composition according to the present invention can preferably have a turbidity of between 200 NTU and preferably between 5 and 100 NTU.
    [0062] The invention also relates to a process for the cosmetic treatment of keratin materials, comprising the application to keratinous substances, in particular the skin, or the oral administration to an individual, of a composition as described previously 25. Said cosmetic treatment method is non-therapeutic. More particularly, the subject of the invention is also a process for the cosmetic treatment of skincare, makeup, and / or cleaning of keratin materials, in particular the skin, comprising the application on said keratin materials, in particular the skin, of a composition according to the invention as described above. Said method of cosmetic treatment of care, makeup, and / or cleansing of the skin is non-therapeutic.
    [0063] More particularly, the subject of the invention is also a cosmetic process for the prevention and / or treatment of cutaneous signs of aging, comprising at least one step of topical application to keratin materials, such as the skin, of a composition according to the invention as described above.
    [0064] The cutaneous signs of the aging to be prevented and / or treated in the cosmetic process according to the invention may be chosen from the lines and wrinkles, and / or to fight against the skin withered, soft and / or thinned.
    [0065] The invention also relates to the cosmetic use of a composition according to the invention as defined above, for the care, makeup and / or cleaning of keratin materials. More particularly, the subject of the invention is the cosmetic use of a composition as defined above, for the care of the skin, preferably for preventing and / or treating the cutaneous signs of aging. In another embodiment, The invention relates to a method for the cosmetic treatment of skincare, makeup, and / or cleaning of keratinous substances, in particular the skin, comprising the administration, orally, to an individual of a composition as defined above. In another embodiment, the invention also relates to the cosmetic use as defined above, in which the combination of hesperetin and at least one organic solvent as defined above, or the composition comprising it, is implementation within a food supplement.
    [0066] Keratinic materials according to the invention include the skin, the body, the face and / or around the eyes, the lips, the nails, the mucous membranes, the eyelashes, the eyebrows, the hairs, the scalp and / or the hair. , or any other skin area of the body. More particularly, the keratin materials according to the invention are the scalp, the hair, and / or the skin.
    [0067] Preferably, the keratin materials according to the invention are the scalp and / or the hair. Preferably the keratin materials according to the invention is the skin. By "the skin" is meant all of the skin of the body, and preferably the skin of the face, décolleté, neck, arms and forearms, or more preferably still, facial skin, including forehead, nose, cheeks, chin, eye area. As specified below, hesperetin is advantageously present in the compositions in accordance with the invention in a solubilized form. By way of example, the composition according to the invention may be intended to be administered topically, that is to say by surface application of the keratin material in question, such as the skin under consideration.
    [0068] The cosmetic composition according to the present invention can be used for a non-therapeutic method, such as a cosmetic process, for treating the skin, the hair, the mucous membranes, the nails, the eyelashes, the eyelids and / or the leather. hairy, by application to the skin, hair, mucous membranes, nails, eyelashes, lashes or scalp. The present invention furthermore relates to a use of the cosmetic composition according to the present invention, as such or in care products and / or detergents and / or make-up products and / or make-up removers for the skin of the skin. body and / or face and / or mucous membranes and / or scalp and / or hair and / or nails and / or eyelashes and / or eyelids. The care product may be a lotion, a cream, a hair tonic, a hair conditioner, a sunscreen, and the like. The cleanser may be a shampoo, a facial cleanser, a hand cleaner, and the like. The makeup product may be a foundation, a mascara, a lipstick, a lip gloss, a blush, an eye shadow, a nail polish, and the like. The makeup remover may be a makeup cleaner and the like.
    [0069] 20 The expressions "between ... and ..." and "from ... to ...", or "at least ..", or "at least .." must be understood as inclusive, except if the opposite is specified. The present invention is described in more detail by way of examples, which should not, however, be construed as limiting the scope of the present invention. The compounds are indicated in chemical name or INCI name. The contents of the ingredients are expressed in percentage by weight.
    [0070] EXAMPLE 1 Evaluation of the Stability and Transparency of Compositions 1 and 3 According to the Invention and Comparative Example 2 Transparency Assessment Protocol: Transparency is Measured with a Hach 2100Q Portable Turbidimeter at 25 ° C. A 60 x 25 cm round borosilicate glass vial with screw cap was used. The amount of sample needed is 15 mL. The measuring range is 0- 1000 NTU. Samples are measured undiluted. The higher the mean Turbidity (NTU) value, the more turbid the composition is and the less transparent it is.
    [0071] Stability Assessment Protocol: The stability of the preparation obtained at time T = 0 and thus after 2 months (T = 2 months) stored at 45 ° C. by a macroscopic control at oail (observation or not of a disorder or a deposit), and by observation under a polarized light microscope (presence or absence of crystals). The following compositions according to Examples 1 and 3 and Comparative Example 2 described below were prepared by mixing the components described in Table 1 as follows: 1) Mixture of ethylhexyl palmitate, and polyglyceryl laurate -5 and polyglyceryl laurate-2 to form an oily phase; (2) heating the oil phase to about 60 ° C; (3) addition of water in the oily phase with stirring to obtain an oil-in-water microemulsion 4) mixture of hesperetin and polyols (dipropylene glycol and butylene glycol, and then adding the solution to the microemulsion (5) addition of preservatives and ethanol.
    [0072] The numerical values for the amounts of the components described in Table 1 are all based on "% by weight of raw materials based on the total weight of the composition.
    [0073] Table 1: Ingredients Composition 1 according to the invention Comparative Example 2 Composition 3 according to the invention hesperetin 0.5 0.5 0.5 (HESPERETIN PURIFIED® from FERRER GRUPO) PHENOXYETHANOL 0.5 0.5 0, 2-ETHYLHEXYL PALMITATE (ETHYL 2 HEXYL PALMITATE (DUB PO) ® from STEARINERIE DUBOIS) 4 4 2 DIPROPYLENE GLYCOL (DIPROPYLENE GLYCOL L0 + 0 from DOW CH EMICAL) 17 17 20 BUTYLENE GLYCOL (1,2-PROPYLENE GLYCOL CAREO) BASF) 10 10 ethanol 5 5 water 52.5 52.5 52.5 OCTANE-1,2-DIOL 0.5 0.5 0.5 (MINACARE OCTIOLO from MINASOLVE) polyglyceryl-2 laurate (SUNSOFT Q- Taiyo Kagaku 12D-C®) 4 0 4 Polyglycerol laurate 1-5 (Taiyo Kagaku SUNSOFT A-121E0) 6 0 5 Macroscopic appearance (naked eye assessment) Clear solution Solution + de-Clear solution Monophasic Monophasic pot ( microemulsion) (microemulsion) Microscopic appearance (evaluation under a microscope under polarized light) no crystallization- Precipitation no crystallization-. The macroscopic appearance, the turbidity and the stability of the oil / water emulsions obtained according to the compositions 1 and 3 in accordance with the invention and the comparative example 2 are as follows: ## EQU1 ## is described in Table 2 below.
    [0074] Evaluation of: Macroscopic appearance Turbidity Average stability (NTU) Composition Transparent fluid 75 at 2 1 monthStable at 45 ° C according to the invention Example Opaque fluid: precipita-> 1000 deposit from comparative 2 important tion and sediment time transparent 70 to 2 3 monthsStable at 45 ° C according to the invention It was thus observed that Comparative Example 2 which is a composition in the form of oil in water emulsion comprising 0.5% hesperetin, and not including especially fatty acid ester and (poly) glycerol, is not stable, and has an opaque appearance with high precipitation, high average turbidity. As is clear from the above results, it has been observed that the compositions 1 and 3 according to the invention, in the form of a nano or microemulsion oil in water and comprising at least one acid ester Fatty acids and (poly) glycerol have a better transparency and are stable at 2 months at 45 ° C, and no crystallization of hesperetin is particularly noted.
    [0075] Example 2: Cosmetic Composition According to the Invention A facial care lotion (oil-in-water emulsion) having the following composition was prepared: 5 Phases Ingredients On 100g A polyglyceryl-2 laurate (SUNSOFT Q-12DCO of Taiyo Kagaku) 4 polyglyceryl laurate (Taiyo Kagaku SUNSOFT A-121E®) 6 2-ETHYLHEXYL PALMITATE (ETHYL 2 HEXYL PALMITATE (DUB PO) ® from STEARINERIE DUBOIS) 4 B water QSP 100 C HESPERETIN 0, 5 (FERRER GRUPO HESPERETIN PURIFIEDO) DIPROPYLENE GLYCOL 17 (DOWROGICAL DIPROPYLENE GLYCOL LO + ®) BUTYLENE GLYCOL (BASF 1,2-PROPYLENEGLYCOL CAREO) D Ethanol 5 preservatives QS Preparation method: 10 (1) ethylhexyl palmitate , polyglyceryl-5 laurate and polyglyceryl-2 laurate were mixed to form an oil phase A; (2) the oily phase A was heated to about 60 ° C; (3) water B was added to the oily phase A with stirring to obtain an oil-in-water microemulsion; (4) mixture of hesperetin and polyols (dipropylene glycol and butylene glycol) were mixed, then solution C was added to the microemulsion. (5) phase D (preservatives and ethanol) was added. The composition is monophasic and limpid, it remains stable and homogeneous after storage for 2 months at 45.degree.
    [0076] This composition can be applied regularly to the skin of the face to reduce the signs of skin aging.
    权利要求:
    Claims (17)
    [0001]
    REVENDICATIONS1. Composition in the form of a nano- or microemulsion, comprising; a) hesperetin: b) at least one fatty acid ester and (poly) glycerol, preferably at least one fatty acid ester and (poly) glycerol formed of at least one acid comprising a chain saturated linear alkyl containing from 12 to 22 carbon atoms and from 1 to 12 glycerol units; c) at least one polyol; d) at least one oil; e) water.
    [0002]
    2. Composition according to the preceding claim, characterized in that hesperetin (a) is present at a content greater than or equal to 0.30% by weight relative to the total weight of the composition, preferably at a content greater than or equal to at 0.50% by weight relative to the total weight of the composition.
    [0003]
    3. Composition according to claim 1, characterized in that the hesperetin (a) is present in a content ranging from 0.05% to 5% by weight, relative to the total weight of the composition, preferably ranging from 0, 20% to 2% by weight, preferably ranging from 0.30% to 1.5% by weight, and particularly ranging from 0.40% to 1% by weight.
    [0004]
    4. Composition according to any one of the preceding claims, characterized in that it comprises at least two fatty acid esters and (poly) glycerol (b) different from each other, preferably at least two fatty acid esters of (poly) glycerol formed from at least one acid comprising a saturated linear alkyl chain containing from 12 to 22 carbon atoms and from 1 to 12 different glycerol units from each other.
    [0005]
    5. Composition according to revendciation 4, characterized in that the first fatty acid ester and (poly) glycerol (b) is selected from a fatty acid ester and (poly) glycerol formed of at least one acid comprising a saturated linear alkyl chain containing from 12 to 18 carbon atoms and from 3 to 6 glycerol units and / or in that the second fatty acid ester and (poly) glycerol (c) is selected from an ester of fatty acid and (poly) glycerol formed from at least one acid comprising a saturated linear alkyl chain containing from 12 to 18 carbon atoms and from 1 to 4 glycerol units.
    [0006]
    6. Composition according to any one of claims 4 or 5, characterized in that the first fatty acid ester and (poly) glycerol (b) is polyglyceryl-5 laurate and / or 3029781 28 in that the second fatty acid ester and (poly) glycerol (c) is polygleryl laurate.
    [0007]
    Cosmetic composition according to any one of the preceding claims, wherein the total amount of the fatty acid ester (s) and (poly) glycerol (b) is present in a certain amount. from 0.50% to 20% by weight, preferably from 2% to 15% by weight, and more preferably from 6% to 12% by weight, based on the total weight of the composition. 10
    [0008]
    8. Composition according to any one of the preceding claims, characterized in that said polyol (c) is chosen from glycerine, diglycerine, polyglycerine, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, 1,3-propanediol, 1,5-pentanediol, polyethylene glycol, and sugars such as sorbitol, and a mixture thereof. 15
    [0009]
    9. Composition according to any one of the preceding claims, characterized in that the (s) said polyol (s) is present (s) in a content ranging from 2% to 50% by weight, relative to the total weight of the composition, preferably ranging from 5% to 40% by weight, and preferably ranging from 20% to 30% by weight.
    [0010]
    10. Composition according to any one of the preceding claims, characterized in that said oil (s) (d) is chosen from the group consisting of vegetable oils, mineral oils, synthetic oils , silicone oils, and hydrocarbon oils.
    [0011]
    11. Composition according to any one of the preceding claims, characterized in that said oil (d) is chosen from oils having a molecular weight of less than 600 g / mol, preferably is ethylhexyl palmitate. 30
    [0012]
    12. A composition according to any one of the preceding claims, wherein the amount of the oil (s) (d) is present in a content of 0.50% to 50% by weight, preferably 1% at 15% by weight, and more preferably from 2% to 5% by weight, based on the total weight of the composition. 35
    [0013]
    A composition according to any one of the preceding claims, wherein the mass ratio [total amount of the fatty acid ester (s) and (poly) glycerol (b) and the oil (s) (d) is from 0.50 to 10, preferably from 1 to 5. 30 29 30 29
    [0014]
    14. Composition according to any one of the preceding claims, characterized in that the ester (s) of fatty acid and (poly) glycerol (b) and hesperetin (a) are present in a ratio [Fatty acid ester (s) and (poly) glycerol (b) / hesperetin (a)] which is at least 2, in particular ranging from 2 to 40, and preferably ranging from 5 to 20.
    [0015]
    15. Composition according to any one of the preceding claims, characterized in that it is in the form of an O / W emulsion, and the oil (e) is in the form of droplets having a mean particle size in number of 300 nm or less, preferably from 10 nm to 150 nm.
    [0016]
    16. Composition according to any one of the preceding claims, characterized in that it is a cosmetic composition. 15
    [0017]
    17. A process for the cosmetic treatment of keratin materials, comprising the application to keratin materials, such as the skin, of a composition according to any one of the preceding claims.
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    同族专利:
    公开号 | 公开日
    WO2016091939A1|2016-06-16|
    FR3029781B1|2018-03-02|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    JP2008184385A|2007-01-26|2008-08-14|Ezaki Glico Co Ltd|Dispersed hesperetin|
    JP2010030967A|2008-07-30|2010-02-12|Ezaki Glico Co Ltd|Dispersed hesperetin|
    EP2359702A1|2010-01-22|2011-08-24|Symrise AG|Solubilization agent for solubilizing polyphenols, flavonoids and/or diterpenoid glucosides|FR3090339A1|2018-12-20|2020-06-26|L'oreal|Composition comprising a monoglyceride, a tartaric ester of monoglyceride, an aromatic polyol ether, a C1-C6 monoalcohol and a C3-C6 diol|
    FR3045338B1|2015-12-18|2019-09-27|L'oreal|COMPOSITION COMPRISING AT LEAST TWO ESTERS OF FATTY ACID ANDGLYCEROL, AND USE THEREOF IN COSMETICS|
    FR3058050B1|2016-10-28|2019-01-25|L'oreal|COMPOSITION COMPRISING AT LEAST TWO ESTERS OF FATTY ACID ANDGLYCEROL, AND USE THEREOF IN COSMETICS|
    JP2020083819A|2018-11-27|2020-06-04|ロレアル|Compositions containing two polyglyceryl fatty acid esters|
    FR3090362B1|2018-12-20|2021-01-08|Oreal|Composition comprising a polysaccharide, a polyol, as well as a particular ester and an oil|
    FR3090360B1|2018-12-20|2021-01-15|Oreal|Composition comprising a polysaccharide, a polyol and a specific ester|
    FR3111549A1|2020-06-19|2021-12-24|L'oreal|Composition comprising a polyol and at least one polyglycerol ester|
    FR3111547A1|2020-06-19|2021-12-24|L'oreal|Composition comprising a polyol and at least one polyglycerol ester|
    WO2021255260A1|2020-06-19|2021-12-23|L'oreal|Composition comprising a polyol and at least one polyglyceryl ester|
    法律状态:
    2015-11-10| PLFP| Fee payment|Year of fee payment: 2 |
    2016-06-17| PLSC| Publication of the preliminary search report|Effective date: 20160617 |
    2016-11-11| PLFP| Fee payment|Year of fee payment: 3 |
    2017-11-13| PLFP| Fee payment|Year of fee payment: 4 |
    2019-09-27| ST| Notification of lapse|Effective date: 20190906 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1462329A|FR3029781B1|2014-12-12|2014-12-12|COMPOSITION COMPRISING HESPERETINE, AN OIL, AT LEAST ONE ESTER OF FATTY ACID ANDGLYCEROL, A POLYOL|
    FR1462329|2014-12-12|FR1462329A| FR3029781B1|2014-12-12|2014-12-12|COMPOSITION COMPRISING HESPERETINE, AN OIL, AT LEAST ONE ESTER OF FATTY ACID ANDGLYCEROL, A POLYOL|
    PCT/EP2015/079095| WO2016091939A1|2014-12-12|2015-12-09|Composition comprising hesperetin, an oil, at least one fatty acid ester of glycerol, and a polyol|
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