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    • 专利摘要:
    Composition (C1) comprising: (a) at least one compound of formula (I): in which each of the radicals Z represents a hydrogen atom or a monovalent radical (Z1): (b) at least one compound of formula (IV ); (c) - a compound of formula (V); process for its preparation and use in cosmetics.
    公开号:FR3013589A1
    申请号:FR1361772
    申请日:2013-11-28
    公开日:2015-05-29
    发明作者:Dimitri Perusse；Thierry Benvegnu；Jerome Guilbot；Herve Rolland
    申请人:Centre National de la Recherche Scientifique CNRS；Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA；Ecole Nationale Superieure de Chimie de Rennes；
    IPC主号:
    专利说明:

    [0001] The invention relates to a novel surfactant composition for use in the preparation of cosmetic and pharmaceutical formulations for topical use. The use of emulsions in cosmetics or dermopharmacy is widespread for the design of hygiene or care products. Formulations of this type make it possible to achieve a harmonious combination, in a homogeneous and easy-to-use form, of an oily phase and of an aqueous phase containing antagonistic ingredients, sometimes lipophilic, sometimes hydrophilic. The emulsifying agents used in these circumstances can be of different natures. If its chemical structure does not carry a charge, this compound is called a surfactant or nonionic surfactant; if it is attached to it a negative charge counterbalanced by a cation, it is an anionic surfactant; if different types of charges coexist on the carbon chain of the same chemical structure it is an amphoteric surfactant and finally, if the chemical structure comprises a positive charge group counterbalanced by an anion, it is a question of a cationic surfactant. The preferred application areas of cationic surfactants are hair products and cosmetic formulas with a strong presence of mineral and / or organic fillers, such as sun products. Creams, especially those for depilatory use, and lotions, may also include such cationic surfactants. Quaternary ammonium cationic surfactants are the most widely used in the cosmetics industry [Martin M. Reiger, "Harry's Cosmeticology", 8th Edition, (2000), Vol. I p. 201, Chemical Publishing]. These include quaternary ammonium structures such as (trimethyl stearyl ammonium chloride) or behenyltrimonium methanesulfonate [Michael and Irene Ash, "Handbook of lubricants", (2012), (2nd Edition), 999, Synapse Information Resources] , marketed for example by Croda under the name I ncroquat Behenyl TMS [EW Flick, "Cosmetic and Toiletry Formulations", (1997), Vol. 6 (2nd Edition), 126, 210, Noyes Publications.], Or of trialkyl benzylammonium type such as the benzyl Dimethyl stearyl ammonium chlorides in the STEPAN range under the brand names Ammonyx [Ernest W. Flick, "Cosmetics additives, An industrial guide "(1991), 725, Noyes Publications]. Access to cationic surfactants today largely relies on a quaternization reaction of an alkyl dimethyl amine with a quaternization agent capable of transferring a carbon group, most often a methyl radical, a reaction that can be illustrate by the following scheme: ## STR2 ## where R 'represents, for example, an alkyl radical containing from 8 to 22 carbon atoms, R' representing a methyl or ethyl radical and Y- representing an anion halide, methylsulfate or ethylsulfate Another approach relies on the involvement of low molecular weight tertiary amines and alkyl halides intended to endow the final structure with a fatty chain and to give it surfactant properties The scheme mentioned above also makes it possible to illustrate it when R 'represents, for example, a methyl radical or a benzyl radical, R "represents an alkyl radical comprising e 8 to 22 carbon atoms and Y- represents an anion halide, methylsulfate, or tosylate. The reagents used according to these two approaches are of synthetic or petrochemical origin, and are dangerous for health and for the environment. This is particularly true for halogenated derivatives and dimethyl and diethyl sulphates. As for fatty dimethyl amines, they generally come from the transformation of fatty acids [Harold A. Wittcoff et al., "Industrial Organic Chemicals" (2004), 419, VViley-Intersciencel, which also involves reagents such as ammonia or hydrogen which are tricky to use and often require the presence of heavy metal catalysts such as cobalt or nickel.
    [0002] It has thus been found necessary to have surfactant cationic derivatives which can be obtained from reagents which do not pose a significant risk to human health and the environment, and which can be used under mild conditions, easy to master on an industrial scale. Glycine betaine, naturally present in some fruits, such as orange or lemon, cereals such as oats, barley or wheat or in beet, has recently emerged as an interesting alternative to traditional ways to reach cationic surfactants [F. Nsimba Zakanda et al. "Thin Solid Films", (2011), 520, 344-350]. This compound in fact carries a positively charged charge and makes it possible to transfer, under suitable conditions, this cationic character to the structure to which it is chemically bonded. Glycine betaine is extracted from beet molasses which represents about 27% of the weight. The international application published under number WO 2005/121294 discloses novel compositions describing mixtures of alkyl hexosides or xylosides and glycine betaine esters or fatty amides that can be used in bactericidal, fungicidal or preservative compositions. The international application published under number WO 2005/121252 discloses the use of glycine betaine derivatives in cold bituminous emulsions and mentions the preparation and glycine betaine esters or amides. The international application published under number WO 2005/121291 discloses the use of glycine betaine derivatives in cosmetic emulsions. The present invention relates to novel compositions which combine fatty esters of glycine betaine, esters of glycine betaine and alkyl polyglucosides which contain in particular structures of alkyl polyglucoside type carrying a cationic group introduced through a controlled grafting of glycine betaine . This is why, according to a first aspect, the subject of the invention is a composition (C1) comprising, for 100 mol%: (a) - from 0.1 mol% to 5 mol% or from a compound of formula ( I): wherein each of the radicals Z represents independently of each other, a hydrogen atom or a monovalent radical (Z1): OZO OZ (Z1) ) in which the X- anion represents an anion chosen from bromide ion, chloride ion, iodide ion, para-toluenesulphonate ion, methanesulphonate ion or trifluoromethanesulphonate ion; it being understood that at least one of the Z radicals does not represent a hydrogen atom; formula (I) in which the radical R2 represents a linear or branched alkyl radical containing from eight to twenty-two carbon atoms, and formula (I) in which m represents a number greater than or equal to 1 and less than or equal to 5; ; or a mixture of compounds represented by said formula (I); (b) - from 45 mol% to 60 mol% or from a compound of formula (IV); The formula (IV) in which the anion X- is as defined for the said radical (Z1) and the radical R2 is as defined for the said formula ( I); or a mixture of compounds represented by said formula (IV); (c) - from 35 mol% to 50 mol% of a compound of formula (V); In which the X- anion is as defined for said radical (Z1); In the definition of the composition (Ci) which is the subject of the present invention, by a mixture of compounds represented by said formula (I), is meant mainly a mixture of two or more compounds represented by the formulas (Ia), (Ib), (1c), (Id) and (Ic): OR 2 OZ - (la) OZ z OO ZO OZ OR2 (Ib) OZ z OO ZO OZ OR2 (I c) OR2 (Id) OZ z OO ZO OZ R2 (le) in the respective molar proportions aa, ab, ac, ad and ae, such that the sum aa + ab + + ad + ae is equal to 1 and that each of the proportions aa, ab, ac, ad and ae is greater than or equal to at zero and less than or equal to one. According to a particular aspect of the present invention, the composition (Ci) as defined above further comprises, for 100 mol%: (d) - from 5% to 15 mol% or of an alcohol of formula (II): R2OH (II) formula (II) in which the radical R2 represents a linear or branched alkyl radical containing from eight to twenty-two carbon atoms; or a mixture of alcohols represented by said formula (II). According to another particular aspect of the present invention, the composition (Ci) as defined above, further comprises, for 100 mol%: (e) - from 20% to 35 mol% of an acid of formula (IX): HX (IX) selected from hydrobromic, hydrochloric, hydroiodic, paratoluenesulfonic, methanesulphonic or trifluoromethanesulphonic acids. According to another particular aspect of the present invention, the composition (Ci) as defined above, further comprises, for 100 mol%: (f) - from 0.1 mol% to 1.5 mol% or from a compound of formula (III): ## STR2 ## wherein R 2 represents a linear or branched alkyl radical having from eight to twenty-two carbon atoms; or a mixture of compounds represented by said formula (III).
    [0003] In the definition of the composition (Ci) which is the subject of the present invention, by a mixture of compounds represented by said formula (III), is meant mainly a mixture of two or more compounds represented by the formulas (IIIa), (IIIb), (111c), (111d) and (IIle): ## STR3 ## wherein R 2 (IIIb) respective molar proportions aa, ab, ac, ad and ae, such that the sum aa + ab + + ad + ae is equal to 1 and that each of the proportions aa, ab, ac, ad and ae is greater than or equal to zero and less than or equal to one.
    [0004] According to another particular aspect of the present invention, the composition (Ci) as defined above, is characterized in that, in the formulas (I), (II), (III) and (IV), the radical R2 is linear and is selected from tetradecyl, hexadecyl, octadecyl, eicosyl or docosyl radicals.
    [0005] According to another particular aspect of the present invention, the composition (Ci) as defined above, is characterized in that, in the formulas (I), (IV) and (V), the X- ion represents the methanesulphonate anion and wherein the acid of formula (IX) is methanesulfonic acid. According to another particular aspect of the present invention, the composition (Ci) as defined above, is characterized in that, in formulas (I) and (III), m is equal to 1. According to another particular aspect of the present invention, The composition (Ci) as defined above, is characterized in that, in formulas (I) and (III), m is greater than 1 and less than or equal to 2.5.
    [0006] The subject of the invention is also a process for the preparation of a composition (Ci), as defined above, characterized in that it comprises a step a), during which 2-trimethylammonioacetate of formula (X): (X) is reacted with a mixture (M1) comprising, for 100 mol%: from 5 mol% to 20 mol%, or from a compound of formula (III), or from a mixture of compounds represented by said formula (III); and from 80% to 95% molar, or an alcohol of formula (II), or a mixture of alcohols represented by said formula (II); in the presence of an excess of acid of formula (IX): HX (IX) to form the composition (CM1) comprising: - either the compound of formula (I) or a mixture of compounds represented by said formula (I); and - either the compound of formula (IV) or a mixture of compounds represented by said formula (IV); and - the compound of formula (V); and a proportion of unreacted compound of formula (X); and optionally a proportion of the alcohol of formula (II) or a mixture of alcohols represented by said unreacted formula (II), and / or the excess of acid of formula (IX) and / or a proportion of the compound of formula (III), a mixture of compounds represented by said formula (III) unreacted.
    [0007] In step a) of the process as defined above, the function of the strong acid of formula (IX) is to convert the carboxylate function of glycine betaine into its protonated form. It is used in a molar stoichiometric excess relative to glycine betaine, generally less than or equal to 4 and in particular between 1.5 and 2.5. Step a) of the process as defined above is carried out at a temperature generally between 50 ° C and 120 ° C, more particularly between 60 ° C and 90 ° C, maintaining the pressure between 5x103Pa and 1.5 x 105 Pa, more particularly between 4 x 102 Pa and 4 x 103 Pa, for a period not exceeding twenty-four hours, generally between ten and twenty hours. The subject of the invention is also the use of a composition (Ci), as defined above, as an emulsifying agent, for preparing emulsions intended for cleaning the skin, the hair, the scalp or the mucous membranes, or topical cosmetic emulsions for the care of skin, hair, scalp or mucous membranes. The term "cleaning the skin, hair, scalp or mucous membranes" means any action intended to allow the removal of dirt on the skin, hair, scalp or mucous membranes of humans or animals. Examples of soiling on the skin, hair, scalp or mucous membranes of humans or animals include dust, dirt, sebaceous secretions, sweat, dandruff, dead cells, microorganisms or various chemical substances such as residues of make-up and skincare compositions, hair, scalp or mucous membranes. The invention finally relates to a cosmetic emulsion (E1) intended for cleaning the skin, the hair, the scalp or the mucous membranes, or for the care of the skin, the hair, the scalp or the mucous membranes, comprising as an agent emulsifier, an effective amount of a composition (C1), as defined above. When used for cosmetic purposes, namely to modify the external appearance of the skin, hair, scalp or mucous membranes, as for example to prevent unsightly effects of aging, or to clean, the emulsion ( E1) object of the present invention is more particularly administered topically. The expression "topical" means that the emulsion (E1) according to the invention is used by application to the skin, the hair, the scalp or the mucous membranes, whether it be a direct application or indirect application, when for example the emulsion (E1) according to the invention is incorporated in a support intended to be brought into contact with the skin (paper, wipe, textile, transdermal device, etc.). The topical emulsion (E1) according to the invention may be packaged in a bottle, and also in pressurized form in an aerosol device or in a "pump bottle" type device, in a device provided with a perforated wall such as, for example a grid, in a device provided with a ball applicator (called "roll-on") The topical emulsion (E1) according to the invention generally comprises chemical additives usually used in the field of formulations for topical use. , in particular cosmetics, dermocosmetics, pharmaceuticals or dermopharmaceuticals, such as foaming and / or detergent surfactants, thickening and / or gelling surfactants, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-polymers. solvents, hydrotropic agents, plasticizers, emulsifiers and co-emulsifiers, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, perfumes, essential oils, preservatives, conditioners, deodorants, bleaching agents for hair and skin discoloration, the active ingredients intended to provide a treating and / or protective action with respect to the skin or the hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients, exfoliating particles, texture agents, optical brighteners, repellents for insects. As examples of foaming surfactants and / or detergents, optionally present in the topical emulsion (E1) according to the invention, mention may be made of foaming surfactants and / or cationic, amphoteric or nonionic detergents. Among the foaming and / or detergent amphoteric surfactants which may be included in the topical emulsion (E1) according to the invention, mention may be made of alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates. Among the foaming and / or detergent cationic surfactants that may be included in the topical emulsion (E1) according to the invention, mention may be made especially of quaternary ammonium derivatives. Among the foaming and / or detergent nonionic surfactants which may be included in the topical emulsion (E1) according to the invention, mention may be made more particularly of alkylpolyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical, and comprising from 8 to 16 carbon atoms, such as octylpolyglucoside, decylpolyglucoside, undecylenylpolyglucoside, dodecylpolyglucoside, tetradecylpolyglucoside, hexadecylpolyglucoside, 1-12 dodecanediylpolyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil"; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines. As examples of thickening and / or gelling surfactants optionally present in the topical emulsion (E1) according to the invention, mention may be made of fatty esters of optionally alkoxylated alkylpolyglycosides, such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose. trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATETM LT and GLUMATETM DOE120; alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate marketed under the name CROTHIX ™ DS53, PEG 55 propylene glycol oleate sold under the name ANTI Ln "141, carbamates of polyalkylene glycols with fatty chains, for example PPG-14. laureth isophoryl dicarbamate marketed under the name ELFACOSTM T211, PPG-14 palmeth-60 hexyl dicarbamate marketed under the name ELFACOSTM GT2125. Examples of thickening and / or gelling agents that may be present in the topical emulsion (E1) according to US Pat. the invention includes polyelectrolytes, linear or branched or crosslinked polymers, such as, for example, the homopolymer of acrylic acid, the homopolymer of methacrylic acid, the homopolymer of the acid 2-methyl- [(1-oxo-2-propenyl) amino] 1-propanesulfonic acid (AMPS), copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of polymers of vinylpyrrolidone and AMPS, copolymers of AMPS and (2-hydroxyethyl) acrylate, copolymers of AMPS and (2-hydroxyethyl) methacrylate, copolymers of AMPS and hydroxyethylacrylamide, copolymers of AMPS and N, N-dimethylacrylamide, copolymers of AMPS and tris (hydronyl) (THAM), copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) acrylate, copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) methacrylate, copolymers of acrylic or methacrylic acid and hydroxyethylacrylamide, copolymers of acrylic or methacrylic acid and THAM, copolymers of acrylic or methacrylic acid and N, N-dimethylacrylamide, terpolymers of acrylic or methacrylic acid, AMPS and (2-hydroxyethyl acrylate), terpolymers of acrylic or methacrylic acid, AMPS and methacrylate (2-hydroxyethyl), terpolymers of acrylic or methacrylic acid, AMPS and THAM, terpolymers of acrylic or methacrylic acid, AMPS and N, N-dimethylacrylamide, terpolymers of acrylic or methacrylic acid, AMPS and acrylamide, copolymers of acrylic acid or methacrylic acid and alkyl acrylates having a carbon chain of from four to thirty carbon atoms and more particularly between ten and thirty carbon atoms, copolymers of AMPS and alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms. The polymers, and more particularly the crosslinked copolymers, terpolymers and tetrapolymers comprising AMPS and macromers, such as those described in the European patent applications published under the numbers EP 1 069 142 A1 and EP 1 339 789 A2, in the international patent application published under the number WO 2011/030044 A1 and in the French patent application published under the number 2 910 899 A1. Polyelectrolytes, linear or branched or crosslinked polymers optionally present in the topical emulsion. (E1) according to the invention may be in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder. The polyelectrolytes, linear or branched or crosslinked polymers optionally present in the topical composition according to the invention can be selected from the products sold under the names SIMULGELTM EG, SIMULGELTMEPG, SEPIGELTM 305, SIMULGELTM 600, SIMULGELTM NS, SIMULGELTM INS 100, SIMULGELTM FL, SIMULGELTM A, SIMULGELTM SMS 88 SEPINOVTMEMT 10 SEPIPLUSTM400, SEPIPLUSTM265, SEPIPLUSTMS, SEPIMAXTMZEN, ARISTOFLEXTM HMB, ARISTOFLEXTMVELVET, ARISTOFLEXTMAVC, ARISTOFLEXTMAVS, NOVEMERTmEC-1, NOVEMERTMEC-2 FLOCARETMET 25 FLOCARETMET 75, FLOCARETMET 26 FLOCARETMET 30 FLOCARETMET 58, FLOCARETMPSD 30, VISCOLAMTMAT 64, VISCOLAMTMAT 100. As examples of thickening and / or gelling agents optionally present in the topical emulsion (E1) according to the invention, mention may be made of polysaccharides consisting solely of monosaccharides, for example Glucans or homopolymers of glucose, glucomannoglucans, xyloglycans, galacs tomannanes whose degree of substitution (DS) of the D-galactose units on the main D-mannose chain is between 0 and 1, and more particularly between 1 and 0.25, such as, for example, galactomannans originating from the gum of cassia (DS = 1/5), locust bean gum (DS = 1/4), tara gum (DS = 1/3), guar gum (DS = 1/2), fenugreek gum (DS = 1). Examples of thickening and / or gelling agents that may be present in the topical emulsion (E1) according to the invention include polysaccharides consisting of monosaccharides, for example sulphated galactans, and more particularly carrageenans, and agar, uronans and more particularly algin, alginates and pectins, heteropolymers of oses and uronic acids and more particularly xanthan gum, gellan gum, exudates of arabic gum and karaya gum, glucosaminoglycans. Examples of thickening and / or gelling agents that may be present in the topical emulsion (E1) according to the invention include cellulose, cellulose derivatives such as, for example, methylcellulose, ethylcellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
    [0008] Examples of stabilizing agents that may be present in the topical emulsion (E1) according to the invention include, for example, microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or sodium chloride. magnesium, silicone polymers such as polysiloxane polyalkyl polyether copolymers.
    [0009] Examples of solvents that may be present in the topical emulsion (E1) according to the invention include water, organic solvents, for example glycerol, diglycerol, oligomers of glycerol, ethylene glycol and propylene. glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said organic solvents. Examples of emulsifying surfactants that may be present in the topical emulsion (E1) according to the invention include nonionic surfactants and cationic surfactants. Examples of emulsifying nonionic surfactants that may be present in the topical emulsion (E1) according to the invention include esters of fatty acids and of sorbitol, for example the products sold under the names MONTANET ™ 40, MONTANET ™ 60, MONTANET ™ 70 , MONTANETm80 and MONTANETm85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, for example the composition comprising stearic acid ethoxylated with 135 moles of ethylene oxide and stearate glycerol marketed under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; alkylpolyglycosides having a linear or branched, saturated or unsaturated aliphatic radical containing from 14 to 36 carbon atoms, for example tetradecylpolyglucoside, hexadecylpolyglucoside, octadecylpolyglucoside, hexadecylpolyxyloside, octadecylpolyxyloside, eicosylpolyglucoside, dodecosylpolyglucoside, 2-octyldodecylpolyxyloside, 12-hydroxystearylpolyglucoside; linear or branched fatty alcohol compositions, saturated or unsaturated, and comprising from 14 to 36 carbon atoms, and alkylpolyglycosides as described above.
    [0010] Examples of cationic emulsifying surfactants that may be present in the topical emulsion (E1) according to the invention include aminoxides, quaternium-82 and the surfactants described in the patent application WO 96/00719 and mainly those whose chain at least 16 carbon atoms, quaternary ammonium compounds, for example trimethyl stearyl ammonium chloride, behenyltrimonium methanesulphonate, trialkyl benzylammonium compounds, for example benzyl dimethyl stearyl ammonium chlorides. Examples of opacifying and / or nacrating agents optionally present in the topical emulsion (E1) according to the invention include sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols having from 12 to 22 carbon atoms. Examples of texturizing agents that may be present in the topical emulsion (E1) according to the invention include N-acyl derivatives of amino acids, such as, for example, lauroyl lysine sold under the name AMINOHOPETMLL, octenyl starch succinate marketed under the name DRYFLOTM, myristyl polyglucoside marketed under the name MONTANOVTM 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica.
    [0011] Examples of deodorant agents that may be present in the topical emulsion (E1) according to the invention include, for example, alkali silicates, zinc salts such as zinc sulphate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3-propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; Triclosan TM; aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulphate, aluminum and zirconium hydrochlorides, aluminum and zirconium trihydrochloride, aluminum zirconium tetrachlorohydrate , aluminum and zirconium pentachlorohydrate, aluminum and zirconium octochlorhydrate, aluminum sulphate, sodium and aluminum lactate, aluminum and glycol hydrochloride complexes, as well as propylene glycol aluminum dihydrochloride complex, aluminum and propylene glycol sesquichlorohydrate complex, polyethylene glycol aluminum aluminum and polyethylene glycol, the complex of aluminum sesquichlorohydrate and polyethylene glycol. Examples of oils that may be present in the topical emulsion (E1) according to the invention include mineral oils such as liquid paraffin, liquid petroleum jelly, isoparaffins or mineral white oils; oils of animal origin, such as squalene or squalane; vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil , pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil, bancoulier oil, passionflower oil , hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula, oils derived from flowers or vegetables vegetable oils ethoxylated; synthetic oils such as fatty acid esters such as butyl myristate, propyl myristate, isopropyl myristate, cetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, hexadecyl stearate, isopropyl stearate, octyl stearate, isocetyl stearate, dodecyl oleate, hexyl laurate, propylene glycol dicaprylate, lanolic acid derived esters, such as isopropyl lanolate, isocetyl lanolate, monoglycerides, diglycerides and triglycerides of fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefin), polyolefins such as polyisobutane ) synthetic isoalkanes such as isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, amine-modified silicones, fatty acid-modified silicones, alcohols-modified silicones, alcohol-modified silicones and fatty acids, modified silicones, polyether groups, modified epoxy silicones, silicones modified with fluorinated groups, cyclic silicones and silicones modified with alkyl groups. By "oils" is meant herein the compounds and / or the mixtures of water-insoluble compounds having a liquid appearance at a temperature of 25 ° C. As examples of waxes that may be present in the topical emulsion (E1) according to the invention, mention may be made of beeswax, carnauba wax, candelilla wax, ouricoury wax, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and solid fatty acids at room temperature; glycerides solid at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, having a solid appearance at a temperature greater than or equal to 45 ° C. Examples of active principles that may be present in the topical emulsion (E1) according to the invention include vitamins and their derivatives, in particular their esters, such as retinol (vitamin A) and its esters (retinyl palmitate, for example ), ascorbic acid (vitamin C) and its esters, ascorbic acid sugar derivatives (for example ascorbyl glucoside) and its esters (for example tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action of the skin, for example w-undecelynoyl phenylalanine sold under the name SEPIWHITETMMSH, SEPICALMTMVG, the mono ester and / or the glycerol diester of w-undecylenoyl phenylalanine, the monoester and / or the erythritol diester of w-undecylenoyl phenylalanine, the mono-ester and / or the xylitol diester of w-undecylenoyl phenylalanine, the mono ester and / or the sorbitol diester of w-undecylenoyl phenylalanine, the wundecylenoyl dipeptides, for example w-undecylenoyl-leucine-leucine, wundecylenoyl-isoleucine-lsoleuci ne, w-undecylenoyl-leucine-lsoleuci ne, w-undecylenoyl-isoleucine-leucine, arbutin, kojic acid, hydroquinone; the compounds showing a soothing action including SEPICALM TM S, allantoin and bisabolol; anti-inflammatory agents; compounds showing a moisturizing action such as, for example, urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides, xylitylplucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM ™, ADIPOLES ™, fucoxanthin; N-acylated proteins; N-acylated peptides such as for example MATRIXILTM; N-acyl amino acids; partial hydrolysates of N-acylated proteins; amino acids; peptides; total hydrolysts of protein; soy extracts, for example Raffermine TM; wheat extracts, for example TENSINETM or GLIADINETM; plant extracts, such as tannin-rich plant extracts, plant extracts rich in isoflavones or plant extracts rich in terpenes; freshwater or marine algae extracts; marine plant extracts; marine extracts in general such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds showing an antimicrobial action or a purifying action, such as, for example, LIPAClDETM C8G, LIPACIDETM UG, SEPICONTROL ™ A5; OCTOPIROXTm or SENSIVATM SC50; compounds showing an energizing or stimulating property such as Physiogenyl ™, panthenol and its derivatives such as SEPICAP ™ MP; anti-aging actives such as SEPILIFTTM DPHP, LIPACIDETM PVB, SEPIVINOLTM, SEPIVITALTM, MANOLIVATM, PHYTO-AGETM, TIMECODETM; SURVICODETM; anti-aging photo active ingredients; the active ingredients protecting the integrity of the dermal-epidermal junction; the active agents increasing the synthesis of the components of the extracellular matrix, for example collagen, elastins, glycosaminoglycans; assets acting favorably on chemical cellular communication such as cytokines or physical ones such as integrins; the active ingredients that create a feeling of "heating" on the skin, such as the activators of cutaneous microcirculation (such as, for example, derivatives of nicotinic acid) or products that create a sensation of "freshness" on the skin (such as menthol for example) and derivatives); the active agents improving cutaneous microcirculation, for example the venotonic ones; draining assets; decongestant assets such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, small holly, centalla asiatica, fucus, rosemary, willow; tanning agents or skin browning agents, such as, for example, dihydroxyacetone, isatin, alloxane, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose.
    [0012] As examples of sunscreens possibly present in the topical emulsion (E1) according to the invention, mention may be made of all those appearing in the cosmetic directive 76/768 / EEC modified Annex VII. Among the solar organic filters optionally present in the topical emulsion (E1) according to the invention, mention may be made of the family of benzoic acid derivatives such as para-aminobenzoic acids (PABA), in particular the monoglycerol esters of PABA, N, N-propoxy PABA ethyl esters, N, Ndiethoxy PABA ethyl esters, N, N-dimethyl PABA ethyl esters, N, N-dimethyl PABA methyl esters, N, N-butyl esters and the like; dimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate; the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate, p-methoxyisopropyl cinnamate , p-methoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (p-methoxy-2-ethyl hexyl cinnamate), p-methoxy 2-ethoxyethyl cinnamate, pmethoxycyclohexyl cinnamate, ethyl-a-cinnamate cyano-8-phenyl, 2-ethylhexyl-α-cyano-p-phenyl cinnamate, glyceryl diparamethoxy mono-2-ethylhexanoyl cinnamate; the family of benzophenone derivatives such as 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2 4-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-4 n-octyloxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3- (4'-methylbenzylidene) -d, 1-ca m phre, 3- (benzylidene) -d, 1-camphor, benzalkonium methosulfate camphor; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as sulfonic acid 2-phenylbenzimidazole-5 and its salts; the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillin-β-carbo-2'-ethylhexyl-t-oxy -1,3,5-triazine, 4,4 - ((6 - (((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazin-2 ester, Benzoic acid 4-diyl diimino) bis- (2-ethylhexyl), 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5 ') t-octylphenyl) benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4 "-t-butylbenzoylmethane, 543,3-dimethyl-2-norbornylidene) -3-pentan-2-one, the family of diphenylacrylate derivatives such as 2-ethylhexyl-2-cyano; 3,3-diphenyl-2-propenoate, ethyl-2-cyano-3,3-diphenyl-2-propenoate, the family of polysiloxanes such as benzylidene malonate siloxane, among the inorganic solar filters, also called "minerals", optionally present in the topical emulsion (E1) according to the invention, mention may be made of titanium oxides, zinc oxides, cerium oxide, zirconium oxide, iron oxides yellow, red or black, chromium oxides These inorganic screens may or may not be micronized, may or may not have undergone surface treatments and may optionally be presented in the form of aqueous or oily pre-dispersions The topical emulsion (E1) according to the invention may be more particularly a suspension of solid particles. Suspended present in the topical emulsion (E1) according to the invention can take different geometries, regular or irregular, and be in the form of beads, beads, rods, flakes, lamellae or polyhedra. These solid particles are characterized by an apparent average diameter of between 1 micrometer and 5 millimeters, more particularly between 10 micrometers and 1 millimeter. Among the solid particles, mention may be made of micas, iron oxide, titanium oxide, zinc oxide, aluminum oxide, talc, silica, kaolin, clays, nitride boron, calcium carbonate, magnesium carbonate, magnesium hydrogencarbonate, inorganic colored pigments, polyamides such as nylon-6, polyethylenes, polypropylenes, polystyrenes, polyesters, acrylic or methacrylic polymers such as polymethyl methacrylates, polytetrafluoroethylene, crystalline or microcrystalline waxes, porous spheres, selenium sulphide, zinc pyrithione, starches, alginates, plant fibers, Loofah particles, sponge particles.
    [0013] The following experimental study illustrates the invention without limiting it. EXAMPLE 1 Preparation of a Composition 19.9 mmol of methanesulphonic acid are added to a 13.33 mmol of glycine betaine reactor, 1.33 mmol of compound of formula (III) in which m is equal to 1, And R2 represents a tetradecyl radical, 11.95 mmol tetradecanol. The mixture thus obtained is placed under reduced pressure (5 to 10 mbar) and is heated at 70 ° C for about eighteen hours. The reaction is followed, on the one hand, by 1H NMR analysis in the solvent CDCl3 / MeOH (1: 1 v / v), and on the other hand, by thin layer chromatography by elution in the AcOEt / AcOH / H20 mixture. (7: 2: 1 v / v / v). The conversion of the compounds of formula (III) into compounds of formulas (I) determined by proton NMR is 39%. The composition (Ci) is obtained, comprising, in molar percentages, the following compounds: Glycine betaine mesylate [Compound of formula (V)]: 19% methanesulfonic acid [Compound of formula (IX)]: 34% tetradecyl alcohol [Compound of the formula Op]: 21% Glycine betaine tetradecyl ester mesylate [Compound of formula (IV)]: 24% Compounds of formula (I) in which R 2 represents a tetradecyl radical: 0.5% Compounds of formula ( III) in which R2 represents a tetradecyl radical: 1.5%. EXAMPLE 2 Preparation of an Emulsion of Interest for the Cosmetic Domain from a Composition According to the Invention The aqueous phase is an aliquot of a demineralised water solution whose pH is previously adjusted to 5.5 by means of controlled additions of acetic acid and sodium acetate. The fatty phase (20 g of a caprylic / capric type triglyceride mixture marketed by the Dubois company under the name Dub MCT ™ 5545) and the aqueous phase (171 g) are previously separately brought to 80 ° C. The emulsifying composition (C1) prepared in Example 1 is dissolved with stirring in the fatty phase, then 1 g of "Caesalpinia spinosa gum" gum sold by the company SEPPIC under the name Solagum Tara is introduced into the fatty phase just before the mixing of the two phases by means of a Silverson brand rotor-stator apparatus. The emulsion thus formed is then brought back to ambient temperature with gentle stirring (150 rpm) with an anchor type mobile. A preservative may possibly be added during this last phase. This type of emulsion remains stable in an oven at 45 ° C for one month.
    [0014] Example 3 Preparation of an Emulsion of Interest for the Cosmetic Domain from a Composition According to the Invention An emulsion was prepared, as in Example 2 above, but without incorporating Caesalpinia spinosa gum gum, the emulsion thus formed remained stable in an oven at 45 ° C. for one month Example 4: Formulations In the following formulas the percentages are expressed as a percentage by mass for 100% of the mass of the formulation 4-1 Day fluid formulation Formula A Composition (C1) 3.00% MONTANOVTm 14: 1.50% DUBTM BB: 2.00% Butyrospermum Parkj (Bio) 1.50% DUBTmMUG: 1.50% Squalane: 3.00% Caprylic / capric triglyceride: 6.00% DUBTmISIP: 3.00% DERMOFEEL TOCO 70TM: 0.10% B Water QS 100.00% Aqueous Hordeum Vulgare extract 3.50% Tara Gum 0.60% C GEOGARDTM 221 0.60% AQUAXYLTM 3.00% DERMOSOFTTM 700 B 0.50% Soda QS pH = 5.5 Procedure: Phase B is added to phase A at a temperature of 80 ° C., with stirring with a turbine of the rotor / stator type, and then cooled with moderate stirring with a mechanical stirrer. united with an anchor-type stirring machine at a speed of 80 rpm. Phase C is then added under the same stirring conditions at a temperature of 40 ° C. 4-2 Intense body firmness milk Formula A Water: Q.S. 100.00% 48% Soda: Q.S. pH = 5.5 AVICELTMPC 611: 0.40% Glycerol: 2.00% B Composition (C1) 2.00% DUBTMISIP 4.00% Caprylic / capric triglyceride 7.00% Carthamus Tinctorius (Safflower) oil 1.00% SEPILIFTTM DPHP 1.00% C Aqueous Hordeum Vulgare extract 10.00% D GEOGARDTM 221 0.60% DERMOFEEL TOCO 70TM 0.10% Fragrance 0.10% Procedure: phase A is added to phase B at 80 ° C under stirring with a rotor / stator turbine. The resulting mixture is then cooled to a temperature of 40 ° C with moderate stirring using a mechanical stirrer with an anchor-type mobile at a speed of 80 rpm. Phase C is then added at 40 ° C, then phase D is then added at 40 ° C. 4-3 Care cream Cyclomethicone: 10% SIMULGELTM EG: 0.8% Composition (C1) 2% Stearyl alcohol: 1% Stearyl alcohol: 0.5% Preservative: 0.65% Lysine: 0.025% EDTA (disodium salt) : 0.05% Xanthan gum: 0.2% Glycerin: 3% Water: qs 100% 4-4 Moisturizing and mattifying foundation FORMULA A water: 20.0% Butylene glycol: 4.0% PEG-400: 4.0% PECOSILTM PS100: 1.0% Sodium hydroxide: q.s. pH = 9 Titanium dioxide: 7.0% Talc: 2.0% Iron oxide yellow: 0.8% Iron oxide red: 0.3% Iron oxide black: 0.05% B LANOLTM 99: 8% Caprylic capric triglyceride 8% Composition (C1): 5.00% C water: qs 100% MICROPEARLTM M305: 2.0% Tetrasodium EDTA: 0.05% D Cyclomethicone: 4.0% Xanthan Gum: 0.2% SIMULGELTM EG: 2.5% E SEPICIDETM HB: 0.5% SEPICIDE Cl: 0 , 3% Fragrance: 0.2% PROCEDURE Prepare at 60 ° C, mix B + D and A + C, then mix and emulsify the whole. 4-5 Capillary mask to rinse FORMULA A MONTANOVTM82: 1.0% SIMULSOLTM 165: 2.5% Cetearyl Alcohol: 1.5% Argania Spinosa kernel Oil 1.0% Hydrogenated Vegetable Oil & Prunus Amygdalus Dulcis Oil & Tocopherol Mineral Oil B Dimethicone & Dimethiconol C Water Composition (C1) D Hydroxyethylcellulose E AQUAXYL'm Phenoxyethanol & Ethylhexylglycerine SEPICAPTM MP Perfume / Fragrance 4-6 Anti-Frizz and Anti-Frizz Hair Spray MONTANOVTML FORMULA: Cyclopentasiloxane & Dimethiconol B SIMULGELTMINS 100 Water C Water Composition (C1) : D SEPICIDETMHB Perfume Lactic acid 3.0% 3.0% Qsp 10 (3.0% '1.0% 0.5% 2.0% 1.2% qs 60% qs 100% 0.5% 1, 0% 0.1% qs pH 5-5.5 The MONTANOVTM 14 is a mixture of myriizine nyristyl alcohol marketed by the company SEPPIC as agent: "rlulsionr DUBTM BB is behenyl behenate marketed by the company STEARINERIE DUBOIS DUBTMMUG is the glycerol undecylenate marketed by the company STEARINERIE DUBOIS BTM ISIP is isoprop yl isostearate marketed by STEARINERIE 30 DUBOIS. DERMOFEEL TOCO 7OTM is a mixture of tocopherols and Helianthus Annus seed oil used as an antioxidant and marketed by the company Dr. Straetmans. DERMOSOFT ™ 700 B: (INCI name: Levulinic Acid / Sodium Levulinate / Glycerin and Water) GEOGARD ™ 221 is a mixture of dehydroacetic acid and benzyl alcohol used as a preservative and marketed by LONZA.
    [0015] AQUAXYLTM (INCI name: Xylitylglucoside,), nhydroxylital 31) is a moisturizing and restruturizing composition of the epidermis marketed by the company SEPPIC. AVICELTM PC 611 is microcrystalline cellulose marketed by the company FMC. SEPILIFTTM DPHP is DiPalmitoylHydroxyProline marketed by the company SEPPIC as active ingredient anti-wrinkle. SIMULGELTM EG: (INCI name: Sodium acrylate / sodium acryloyldimethyl taurate copolymer and Isohexadecane and Polysorbate 80) marketed by the company SEPPIC; PECOSILTMPS 100 is dimethicone PEG-7 marketed by the company PHOENIX. MICROPEARL ™ M 305 is a silky, water-dispersible powder based on a cross-linked methyl methacrylate copolymer. LANOLTM 99 is isononyl isononanoate marketed by the company SEPPIC. SEPICIDETM HB, which is a mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative marketed by the company SEPPIC.
    [0016] SEPICIDETM Cl, imidazolidine urea, is a preservative marketed by the company SEPPIC.SIMULSOLT 165 is a mixture of PEG-100 Stearate and Glyceryl Stearate SEPICAPTMMP (INCI name: sodium cocoyl amino / potassium dimethicone copolyol prithenyl phosphate.
    [0017] LTANOVTmE32 (INCI name: Cetearyl Alcohol (and) Coco glucoside) is a nonionic emulsifier sold by the company SEPPIC. DATANOV ™ (INCI name: C14-22 Alcohol (and) C12-20 Glucoside) is an EEPPIC agent. SIMULGELTmlf 3100 (INCI name H / Sodium AcryloyI :: Copolymer Isohexadecane a thick agent by the company SEPPIC.
    权利要求:
    Claims (11)
    [0001]
    REVENDICATIONS1. Composition (C1) comprising, for 100 mol%: (a) - from 0.1 mol% to 5 mol% or from a compound of formula (I): ## STR2 ## ) in which each of the Z radicals independently represents one of the two other, a hydrogen atom or a monovalent radical (Z1): ## STR2 ## in which the X- anion represents an anion selected from bromide ion, chloride ion, iodide ion, para-toluenesulfonate ion, methanesulfonate ion or trifluoromethanesulfonate ion; it being understood that at least one of the Z radicals does not represent a hydrogen atom; formula (I) in which the radical R 2 represents a linear or branched alkyl radical containing from eight to twenty-two carbon atoms, and formula (I) in which m represents a number greater than or equal to 1 and less than or equal to 5; ; or a mixture of compounds represented by said formula (I); (b) - from 45 mol% to 60 mol% or from a compound of formula (IV); Or wherein the anion X- is as defined for said radical (Z1) and the radical R2 is as defined for said formula (I); or a mixture of compounds represented by said formula (IV); (c) - from 35% molar to 50% molar of a compound of formula (V): ## STR2 ## in which the anion X- is as defined for said radical (Z1 );
    [0002]
    2. Composition (C1) as defined in claim 1 further comprising, for 100 mol%: (d) - 5% to 15 mol% or an alcohol of formula (II): R20 H (II) formula (II) in which the radical R 2 represents a linear or branched alkyl radical containing from eight to twenty-two carbon atoms; or a mixture of alcohols represented by said formula (II).
    [0003]
    3. Composition (C1) as defined in any one of claims 1 or 2 further comprising, for 100 mol%: (e) - from 20% to 35 mol% of an acid of formula (IX): HX (IX) chosen from hydrobromic, hydrochloric, hydroiodic, para-toluenesulphonic, methanesulphonic or trifluoromethanesulphonic acids.
    [0004]
    4. Composition (C1) as defined in any one of claims 1 to 3, further comprising, for 100 mol%: (f) - from 0.1 mol% to 1.5 mol% or from a compound of formula (III): H OR2 (III) formula (III) in which the radical R2 represents a linear or branched alkyl radical containing from eight to twenty-two carbon atoms; or a mixture of compounds represented by said formula (III).
    [0005]
    5. A composition as defined in any one of claims 1, 2 or 4, wherein in the formulas (I), (II), (III) and (IV), the radical R2 is linear and is selected from tetradecyl, hexadecyl, octadecyl, eicosyl or docosyl radicals.
    [0006]
    6. Composition as defined in any one of claims 1, 3 or 4, wherein in the formulas (I), (IV) and (V), the X- ion represents the methanesulfonate anion and for which the The acid of formula (IX) is methanesulfonic acid.
    [0007]
    7. Composition as defined in any one of claims 1 or 4, wherein in the formulas (I) and (III), m is equal to 1.
    [0008]
    8. Composition as defined in any one of claims 1 or 4, wherein in formulas (I) and (III), m is greater than 1 and less than or equal to 2.5.
    [0009]
    9. Process for the preparation of a composition (C1), as defined in any one of Claims 1 to 8, characterized in that it comprises a step a), during which the 2-trimethylammonioacetate of formula ( X): Me Me N + Me is reacted with a mixture (M1) comprising for 100 mol%: - 5 mol% to 20 mol% or a compound of formula (III), or a mixture of compounds represented by said formula (III); and from 80% to 95% molar, or an alcohol of formula (II), or a mixture of alcohols represented by said formula (II); in the presence of an excess of acid of formula (IX): HX (IX) to form a mixture (M2) comprising: - either the compound of formula (I) or a mixture of compounds 4 represented by said formula (I); and - either the compound of formula (IV) or a mixture of compounds represented by said formula (IV); and - the compound of formula (V); and a proportion of unreacted compound of formula (X); and (X) optionally a proportion of the alcohol of formula (II) or a mixture of alcohols represented by said unreacted formula (II), and / or the excess of acid of formula (IX and / or a proportion of the compound of formula (III), a mixture of compounds represented by said formula (III) unreacted.
    [0010]
    10. Use of a composition (Ci), as defined in any one of claims 1 to 8, as an emulsifying agent, for preparing emulsions for cleaning the skin, hair, scalp or mucous membranes, or topical cosmetic emulsions for the care of skin, hair, scalp or mucous membranes.
    [0011]
    11. Cosmetic emulsion (E1) intended for cleaning the skin, hair, scalp or mucous membranes, or for the care of the skin, the hair, the scalp or the mucous membranes, comprising as emulsifying agent, an effective amount of a composition (Ci) as defined in any one of claims 1 to 8.
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    法律状态:
    2015-11-19| PLFP| Fee payment|Year of fee payment: 3 |
    2016-09-26| PLFP| Fee payment|Year of fee payment: 4 |
    2017-09-11| PLFP| Fee payment|Year of fee payment: 5 |
    2017-11-24| TQ| Partial transmission of property|Owner name: L'ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENN, FR Effective date: 20171023 Owner name: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, FR Effective date: 20171023 |
    2018-11-29| PLFP| Fee payment|Year of fee payment: 6 |
    2020-10-16| ST| Notification of lapse|Effective date: 20200914 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1361772A|FR3013589B1|2013-11-28|2013-11-28|COMPOSITION OF ALKYL POLYGLUCOSIDES AND CATIONED FATTY ACIDS|FR1361772A| FR3013589B1|2013-11-28|2013-11-28|COMPOSITION OF ALKYL POLYGLUCOSIDES AND CATIONED FATTY ACIDS|
    CA2931395A| CA2931395A1|2013-11-28|2014-11-26|Composition of alkyl polyglucosides and fatty esters of cationic amino acids|
    PCT/EP2014/075620| WO2015078893A1|2013-11-28|2014-11-26|Composition of alkyl polyglucosides and fatty esters of cationic amino acids|
    EP14808550.9A| EP3073988A1|2013-11-28|2014-11-26|Composition of alkyl polyglucosides and fatty esters of cationic amino acids|
    US15/100,142| US10149810B2|2013-11-28|2014-11-26|Composition of alkyl polyglucosides and fatty esters of cationic amino acids|
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