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EP1043972A1 - Verwendung von estergruppe enthaltenden silikonen als übertragungswiderstandsmittel in kosmetischen zubereitungen - Google Patents

Verwendung von estergruppe enthaltenden silikonen als übertragungswiderstandsmittel in kosmetischen zubereitungen

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Publication number
EP1043972A1
EP1043972A1 EP98967123A EP98967123A EP1043972A1 EP 1043972 A1 EP1043972 A1 EP 1043972A1 EP 98967123 A EP98967123 A EP 98967123A EP 98967123 A EP98967123 A EP 98967123A EP 1043972 A1 EP1043972 A1 EP 1043972A1
Authority
EP
European Patent Office
Prior art keywords
cosmetic compositions
ester
formula
symbols
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98967123A
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English (en)
French (fr)
Inventor
Jean-Marc Ricca
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhodia Chimie SAS
Original Assignee
Rhodia Chimie SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodia Chimie SAS filed Critical Rhodia Chimie SAS
Publication of EP1043972A1 publication Critical patent/EP1043972A1/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the present invention relates to the use of liquid organopoiysiloxanes (silicones) with ester functions (acetoxyalkyls) as anti-transfer agents in cosmetic compositions. It also relates to a process for providing anti-transfer properties to cosmetic compositions by adding to said compositions at least one liquid polyorganosiloxane with ester functions (acetoxyalkyls), as well as cosmetic compositions, in particular in the form of sun gels, deodorants. , antiperspirants, make-up or care products, comprising said liquid polyorganosiloxane with ester functions (acetoxyalkyls).
  • liquid polyorganosiloxanes comprising acetoxyalkyl functions in which the alkyl group contains at least 3 carbon atoms, were very particularly advantageous for imparting anti-transfer properties to certain cosmetic compositions, in particular to make-up formulations, while providing a sensory profile closely resembling that of conventional non-transfer formulations.
  • a first subject of the invention therefore consists in the use as anti-transfer agents, in cosmetic compositions, of polyorganosiloxanes with ester functions of formula (I) below:
  • R 1 , R 2 are identical or different and represent.
  • R 7 represents a linear or branched C- alkyl radical
  • R 4 , R ⁇ and R> are identical or different and represent a C 1 to C 6 alkyl or phenyl radical, preferably methyl
  • R 7 represents a linear or branched C1 to C4 alkyl radical, preferably methyl
  • R ' represents a linear or branched C3 - C20 alkylene group. preferably in C3 - C-j 2. very particularly trimethylene or 2-methyl trimethylene,.
  • - ⁇ represents an average number greater than or equal to 0, preferably ranging from 5 to 100
  • - a represents an average number greater than or equal to 0, preferably ranging from 1 to 50, very particularly ranging from 1 to 30, at least one of the symbols R 3 representing the symbol Q ester of formula (1) when a is equal to 0, said polyorganosiloxanes having ester functions being in liquid form under normal conditions of temperature and pressure.
  • a second subject of the invention consists in a process for providing anti-transfer properties to cosmetic compositions by adding to said compositions at least one polyorganosiloxane with ester functions of formula (I), said polyorganosiloxane with ester functions being present in liquid form under normal conditions of temperature and pressure.
  • a third subject of the invention consists of cosmetic compositions comprising at least one polyorganosiloxane with ester functions of formula (I), said polyorganosiloxane with ester functions being in liquid form under normal conditions of temperature and pressure.
  • . ⁇ represents an average number of the order of 0 to 500, preferably of the order of 5 to
  • . ⁇ ! represents an average number of the order of 0 to 100, preferably of the order of 0 to 20
  • . al represents an average number of the order of 1 to 50, preferably of the order of 1 to
  • Q represents an acetoxyalkyl function of formula - ROCOCH3 or an alcohol function -R'OH, where R 'represents a trimethylene or 2-methyltrimethylene group, very particularly trimethylene, at least one of the symbols Q representing an acetoxyalkyl function - ROCOCH3.
  • R ' represents a trimethylene or 2-methyltrimethylene group, very particularly trimethylene
  • all the symbols Q represent an ester function.
  • Said polyorganosiloxanes containing ester functions of formula (I) can be obtained by * hydrosilylation between a hydrogenopolyorganosiloxane oil of formula (V)
  • R 3 ' represents. a linear or branched C- alkyl radical
  • R 7 represents a linear or branched C 1 to C 8 alkyl radical, preferably methyl and an olefinic alcohol of formula ROH, formula in which R represents an olefinic radical from which the bivalent radical R 'is derived by opening the double bond in ⁇ and adding hydrogen, preferably an allyl or methallyl radical, * then esterification of the hydroxyalkylated polyorganosiloxane of formula (VI) obtained
  • R 7 has the definition given above
  • X represents a halogen atom, notably chlorine.
  • the hydrosilylation step can be carried out in a well known manner at a temperature of the order of 20 ° C to 200 ° C, preferably of the order of 60 ° C to 120 ° C, in the presence of a hydrosilylation catalyst, in particular based on platinum.
  • the relative amounts of hydrogenopolyorganosiloxane of formula (V) and ⁇ olefinic alcohol ROH generally correspond to a molar ratio ⁇ olefinic alcohol / hydrogenopolyorganosiloxane greater than 1 and less than or equal to 5, preferably greater than 1 and less than or equal to 2.
  • Excess olefinic alcohol can be removed by vacuum distillation.
  • the hydrogenopolyorganosiloxane used in the hydrosilylation step is preferably chosen from those of formulas: Me 3 Si O (SiMe 2 O) p - (SiMeHO) q - SiMe 3
  • . ⁇ ! represents an average number of the order of 0 to 100, preferably of the order of 0 to 20
  • . if represents an average number of the order of 1 to 50, preferably of the order of 1 to 30.
  • the ⁇ olefinic alcohol of formula ROH used in the hydrosilylation stage is preferably allylic or methallylic alcohol.
  • the esterification operation can be carried out at a temperature of the order of 0 ° C to 100 ° C, preferably of the order of 25 ° C to 50 ° C, in the absence or in the presence of a esterification catalyst.
  • hydroxyalkylated polyorganosiloxane and of acyl halide of formula XCOR generally correspond to a molar ratio of acyl halide / hydroxy-alkylated polyorganosiloxane of the order of 0.1 to 2, preferably of the order of 0.1 to 1.
  • acyl halide of formula XCOR "most particularly used in the esterification step is acetyl chloride.
  • the acid halide formed by esterification can be removed by entrainment using an inert gas, then by treatment with a base. After devolatization of the by-products, the polyorganosiloxane having an ester function can then be recovered by filtration, for example.
  • This process has the advantage of leading to polyorganosiloxanes with ester functions, of very high purity, that is to say products in which the overall contents of olefinic siloxane units and / or olefinic impurities, with undesirable effects. or capable of reacting, correspond to a number of ⁇ olefinic groups per 100 g of polyorganosiloxane with ester function obtained less than 10 ⁇ 3 , preferably less than 5 ⁇ 1 O * 4 .
  • ⁇ olefinic siloxane units and ⁇ olefinic impurities are those of formulas - Si - O - R, ROH and R "COOR, where R represents an ⁇ olefinic radical, linear or branched, having 3 to 20 carbon atoms, as defined above (allyl or methallyl for example).
  • the polyorganosiloxanes with ester functions of formula (I) are present in the liquid state under normal conditions of temperature and pressure, that is to say at a temperature of the order of 10 to 30 ° C under atmospheric pressure . They have viscosities generally less than 5000 mPa.s.
  • cosmetic composition or formulation means all cosmetic products or preparations such as those described in Annex I ("illustrative list by category of cosmetic products") of European Directive No. 76/768 / EEC of July 27, 1976, so-called cosmetic directive.
  • said polyorganosiloxanes with ester functions of the above formulas can be used at a rate of 0.1% to 30%, preferably from 3% to 10% by weight said cosmetic compositions.
  • the cosmetic compositions containing said polyorganosiloxanes with ester functions of the above formulas as anti-transfer agents can be formulated in a large number of types of products for the skin and / or the hair (or more generally keratin), such as foams. , gels (especially styling), conditioners, formulations for styling or to facilitate combing of hair, rinsing formulas, hand and body lotions, products regulating the hydration of the skin, toilet milks, makeup-removing compositions, creams or lotions for protection against the sun and ultraviolet radiation, care creams, anti-acne preparations, local analgesics, mascaras, deodorants , antiperspirants, lipsticks and many other compositions of the same type.
  • said polyorganosiloxanes having ester functions are used in cosmetic anti-transfer compositions for the skin.
  • Said cosmetic compositions may use a vehicle or a mixture of vehicles compatible with application to the hair and / or the skin.
  • Said vehicle can represent from 0.5% to 99.5% approximately of the weight of said composition, preferably from 5 to 90% approximately.
  • the term "compatible with an application on the hair and / or the skin” means here that the other vehicle does not damage or exert any negative effects on the appearance of the hair and / or the skin or does not create no skin and / or eye and / or scalp irritation.
  • the vehicles compatible with the applications described in this invention include those usually used in cosmetic compositions for the hair and / or the skin, for example those present in sprays, mousses, tonics, gels, shampoos, or lotions rinse.
  • the choice of the appropriate vehicle will depend on the nature of the ingredients used, and the destination of the formulated product, depending on whether it is supposed to be left on the surface where it has been applied (e.g. sprays, foams, tonic lotion, cream, or gels) or rinsed off after use (e.g. shampoo, conditioner, rinse lotions).
  • Said vehicles can consist of at least one solvent to dissolve or disperse the ingredients used, such as water, Cf-Cg alcohols, and their mixtures (in particular water and methanol, ethanol, isopropanol, and mixtures thereof), or other solvents such as acetone, hydrocarbons (such as isobutane, hexane, decane), halogenated hydrocarbons (such as freons), linalool, esters (such as acetate, dibutyl phthalate), volatile silicones (in particular phenyl pentamethyl siloxane, methoxypropyl heptamethyl cyclotetrasiloxane, chloropropyl pentamethyldisiloxane, hydroxypropyl pentamethyl disiloxane, octamethyl cyclotetrasiloxane, decamethyl cycloxane hexamethyl disiloxane, octamethyltrisiloxane, deca
  • All of the vehicles used can consist of solvents which are miscible or immiscible with each other.
  • the preferred preferential solvents include water, ethanol, volatile silicones and their mixtures.
  • Foams and aerosol sprays can also use any propellant capable of generating the products in the form of foam or in the form of fine, uniform sprays.
  • the polyorganosiloxanes with ester function of formula (I) are particularly well suited for uses as anti-transfer agents in cosmetic compositions containing at least 3%, preferably from 5 to 90% of alcoholic solvents such as ethanol, propylene glycol , glycerol.
  • Vehicles can take many forms, for example, the form of emulsions including water in oil, oil in water emulsions, and multiple emulsions. These emulsions cover a wide viscosity range, from 100 to 2,000,000 mPa.s. .
  • These emulsions can also be delivered in the form of foams or sprays using either a device of the mechanical pump type, or in the form of an aerosol pressurized by the use of a propellant gas. They can also be rheologically modified (increase in viscosity) for example by the addition of gums, resins, polymers, waxes or salts.
  • At least 0.5% of at least one cosmetically acceptable ingredient may be present in said cosmetic compositions.
  • compositions can comprise at least one surfactant.
  • the polyorganosiloxanes having an ester function of formula (I) can be present in said compositions in the form of dispersed particles of size which can range from 0.02 to 100 microns (emulsions), or in the form of microemulsions.
  • Said cosmetic compositions can comprise:
  • At least one polyorganosiloxane with ester function of formula (I) are used to disperse, emulsify, dissolve and stabilize the various constituents of the composition, in particular those used for their anti-transfer, emollient or humectant properties.
  • the surfactants which may be present in said cosmetic compositions may be of the anionic, nonionic, cationic, zwitterionic or amphoteric type; examples that may be mentioned include anionic surfactants such as
  • alkyl sulfonate esters of formula R-CH (S ⁇ 3M) -COOR ' where R represents a C8-C 2 o alkyl radical. preferably in Cio-C-ig, R 'an alkyl radical in Cj-Cg, of preferably in C-
  • alkyl sulphates of formula ROSO3M where R represents a C-jo-C 2 4, preferably C-, alkyl or hydroxyalkyl radical
  • OE ethoxylenated
  • OP propoxylenated
  • the sulfonated alkylamides of formula RCONHROSO3M where R represents a C 2 -C 22 , preferably C 1 -C 22 alkyl radical, R 'a C -C 3 alkyl radical, M representing a hydrogen atom or a cation of the same definition as above, as well as their ethoxylenated (OE) and / or propoxylenated (OP) derivatives, having on average from 0.5 to 60 OE and / or OP units;
  • alkylglycerol sulfonates sulfonated polycarboxylic acids described in GB-A-1 082 179, paraffin sulfonates, N-acyl N-alkyltaurates, alkylphosphates, alkylisethionates, alkylsuccinamates, alkylsulfosuccinates, monoesters or diesters of sulfosuccinates, N-acyl sarcosinates, alkyl glycoside sulfates, polyethoxycarboxylates, the cation being an alkali metal (sodium, potassium, lithium), a substituted or unsubstituted ammonium residue (methyl-, dimethyl-, trimethyl-, tetramethylammonium, dimethylpiperidinium, etc.).
  • alkali metal sodium, potassium, lithium
  • a substituted or unsubstituted ammonium residue methyl-, dimethyl-, trimethyl-,
  • non-ionic surfactants such as: polyoxyalkylenated (polyethoxyethylenated, polyoxypropylenated, polyoxybutylenated) alkylphenols in which the alkyl substituent is Cg-C-
  • glycerolamides derived from N-alkylamines (US-A-5,223,179 and FR-A-1,585,966). polyoxyalkylenated Cg-C 22 aliphatic alcohols containing from 1 to 25 oxyalkylene units (oxyethylene, oxypropylene); by way of example, mention may be made of TERGITOL 15-S-9, TERGITOL 24-L-6 NMW sold by Union Carbide Corp., NEODOL 45-9, NEODOL 23-65, NEODOL 45-7, NEODOL 45-4 marketed by Shell Chemical Cy., KYRO EOB marketed by The Procter & Gamble Co. . the products resulting from the condensation of ethylene oxide with a hydrophobic compound resulting from the condensation of propylene oxide with propylene glycol, such as the Pluronic sold by BASF;
  • amine oxides such as Cig-Ci g dimethylamine oxides, Cg-C2 2 alkoxy ethyl dihydroxy ethylamines;
  • R1 has the above meaning and most often represents coconut and lauryl chains.
  • alkyl polyamines such as AMPHIONIC XL® marketed by RHONE-POULENC, AMPHOLAC 7T / X® and AMPHOLAC 7C / X® marketed by AKZO NOBEL.
  • the polyorganosiloxanes having an ester function of formula (I) also have a good affinity for surfaces, and, by their silicone character, contribute to the apparent modification of these surfaces, this being able to result in the case of the hair by more combability. easy on wet hair or an increase in shine or volume, and in the case of the skin by a sensory signal.
  • Said cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used can therefore also contain non-water-soluble and non-volatile organopolysiloxanes (also called hereinafter "non-water-soluble and non-volatile silicones").
  • non-water-soluble and non-volatile organopolysiloxanes also called hereinafter "non-water-soluble and non-volatile silicones”
  • Said organopolysiloxanes are considered to be non-water-soluble and non-volatile when their solubility in water is less than 50 grams / liter and their intrinsic viscosity is at least 300 mPa.s. at 25 ° C.
  • silicone gums such as, for example, diphenyl dimethicone gum sold by the company Rhône-Poulenc, and preferably polydimethylsiloxanes having a viscosity at least equal to 60,000 mPa.s. at 25 ° C, and even more preferably, those with a viscosity greater than 2,000,000 mPa.s. at 25 ° C, such as the Mirasil DM 500000® sold by the company Rhône-Poulenc.
  • the cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used may also contain conditioning agents.
  • conditioning agents which can be used in the context of this invention, there are conditioning agents of animal origin, such as hydrolysates of animal proteins, such as the ammonium salt of dimethyl- or trimethyl stearate of collagen hydrolysates, silk, keratin; conditioning agents of synthetic origin, better known under the name polyquaternium, such as the copolymer of N, N'-bis ((dimethylamino) -3 propyl) urea and oxy-1,1 'bis (chloro-2) ethane or polyquaternium-2, the copolymer of diallyidimethyl ammonium chloride and acrylamide or polyquaternium-7; cationic derivatives of polysaccharides, such as cocodimonium hydroxyethyl cellulose, guar hydroxypropyl trimonium chloride, hydroxypropyl guar hydroxyprop
  • Conditioners are preferably chosen from conditioners of synthetic origin, in particular polyquaterniums -2, -7, and -10, and cationic derivatives of polysaccharides, such as cocodimonium hydroxyethyl cellulose, guar hydroxypropyl trimonium chloride, l 'hydroxypropyl guar hydroxypropyl trimonium chloride.
  • guar derivatives such as guar hydroxypropyl trimonium chloride and hydroxypropyl guar hydroxypropyl trimonium chloride.
  • the anti-transfer cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used may also contain polymers with film-forming properties which can also be used as fixing resins. These polymers with film-forming properties are generally present in said compositions at concentrations of between 0.01 and 10%, preferably between 0.5 and 5%.
  • the polymers with film-forming properties are preferably chosen from the following oligomers, polymers, copolymers or resins: * methyl acrylate / acrylamide copolymers, polyvinylmethylether / maleic anhydride copolymers, vinyl acetate / crotonic acid copolymers, octylacrylamide / methyl acrylate / butylaminoethylmethacrylate copolymers, polyvinylpyrrolidones, polyvinylpyrrolidone / methyl methacrylate copolymers, polyvinylpyrrolidone / vinyl acetate copolymers, polyvinyl alcohols, polyvinyl alcohol / crotonic acid copolymers, polyvinyl alcohol / maleic anhydride copolymers, hydroxypropyl celluloses, hydroxypropyl guyrones, hydroxyalkyl polypropylene guards, hydroxyalkyl hydroxypropyl guar
  • polyester copolymers based on ethylene terephthalate and / or propylene terephthalate and polyoxyethylene terephthalate units (US-A-3,959,230, US-A-3,893,929, US-A-4,116,896, US-A-4,702,857, US-A-4770666); . sulfonated polyester oligomers obtained by sulfonation of an oligomer derived from ethoxylated allyl alcohol, dimethyl terephthalate and 1,2 propylene diol (US-A-4968451) .
  • polyester copolymers based on propylene terephthalate and polyoxyethylene terephthalate units and terminated by ethyl or methyl units (US-A-4,711,730) or polyester oligomers terminated by alkylpolyethoxy groups (US-A-4,702,857) or groups anionic sulfopolyethoxy (US-A-4,721,580), sulfoaroyl (US-A-4877 896)
  • the polyester polyurethanes obtained by reaction of a polyester obtained from adipic acid and / or terephthalic acid and / or sulfoisophthalic acid and a diol, on a prepolymer with terminal isocyanate groups obtained from a polyoxyethylene glycol and a diisocyanate (FR-A-2334698).
  • FR-A-2334698 ethoxylated onoamines or polyamines, ethoxylated amine polymers
  • polyester oligomers obtained by condensation of isophthalic acid, of dimethyl sulfosuccinate and of diethylene glycol (FR-A-2236 926).
  • copolymers comprising polyester units derived from dimethyl terephthalate, isophthalic acid, dimethyl sulfoisophthalate and ethylene glycol and polyorganosiloxane units (FR-A-2728915).
  • cationic resins derived in whole or in part from cationic monomers such as, for example, dimethylaminoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethyl ammonium chloride, or mixtures thereof.
  • the film-forming polymers are of the polyvinylpyrrolidone (PVP) type, polyvinylpyrrolidone and methyl methacrylate copolymers, polyvinylpyrrolidone and vinyl acetate (VA) copolymer, polyterephthalic ethylene glycol / polyethylene glycol copolymers, polyterephthalate copolymers. ethylene glycol / polyethylene glycol / sodium polyisophthalate sulfonate, and mixtures thereof. These film-forming polymers are preferably dispersed or dissolved in the chosen vehicle.
  • PVP polyvinylpyrrolidone
  • VA vinyl acetate copolymer
  • VA vinyl acetate copolymer
  • polyterephthalic ethylene glycol / polyethylene glycol copolymers polyterephthalate copolymers.
  • ethylene glycol / polyethylene glycol / sodium polyisophthalate sulfonate and mixtures thereof.
  • the anti-transfer cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used may also contain polymeric derivatives exerting a protective function.
  • These polymer derivatives can be present in said compositions in amounts of the order of 0.01-10%, preferably about 0.1-5%, and very particularly of the order of 0.2-3% by weight, agents such as:
  • cellulose derivatives such as cellulose hydroxyethers, methylcellulose, ethylcellulose, hydroxypropyl methylcellulose, hydroxybutyl methylcellulose.
  • polyvinyl esters grafted on polyalkylene trunks such as polyvinyl acetates grafted on polyoxyethylene trunks (EP-A-219048).
  • polyvinyl alcohols such as polyvinyl alcohols
  • the performance of said cosmetic compositions can also be improved by the use of plasticizing agents. These constitute from 0.1 to 20% of the formulation, preferably from 1 to 15%.
  • plasticizing agents there may be mentioned adipates, phthalates, isophthalates, azelates, stearates, silicone copolyols, glycols, castor oil, or mixtures thereof.
  • metal sequestering agents more particularly those sequestering calcium such as citrate ions.
  • Humectants can also be incorporated into these cosmetic compositions; there may be mentioned glycerol, sorbitol, urea, collagen, gelatin, aloe vera, hyaluronic acid, and emollients which are generally chosen from alkylmonoglycerides, alkyldiglycerides, triglycerides such as oils extracted from plants and plants (palm, copra, cottonseed, soybean, sunflower, olive, grapeseed, sesame, peanut, castor oil, etc.) or animal origin (tallow, fish oils, Among, derivatives of these oils such as hydrogenated oils, lanolin derivatives, mineral oils or paraffinic oils, perhydrosqualane, squalene, diols such as 1 - 2-propanediol, 1 -3-butanediol, cetyl alcohol, stearyl alcohol, oleic alcohol, polyethylene glycols or polypropylene glycols, fatty esters such as isoprop
  • water-soluble or water-dispersible polymers such as collagen or certain non-allergenic derivatives of animal or vegetable proteins (wheat protein hydrolysates for example), natural hydrocolloids ( guar, carob, tara gum) or derived from fermentation processes and derivatives of these polycarbohydrates such as modified celluloses (for example hydroxyethylcellulose, carboxymethylceliulose), guar or carob derivatives such as their cationic derivatives or non-derivatives -ionics (for example hydroxypropylguar), anionic derivatives (carboxymethylguar and carboxymethyl hydroxypropylguar).
  • Specific anti-transfer cosmetic compositions in which the polyorganosiloxanes having an ester function of formula (I) are used as anti-transfer agents are those comprising an oily medium.
  • oily media there may be mentioned, for example, those whose main fatty phase is of the type
  • the amount of polyorganosiloxane having an ester function of formula (I) which can be used in said oily media is preferably of the order of 0.2 to 50, preferably of the order of 2 to 10 parts by weight per 100 parts in weight of said oily media.
  • a fatty phase is considered to be the main in an oily medium, when the latter represents of the order of at least 10%, preferably at least 40% by weight of said oily medium.
  • PPG polypropylene glycol
  • WITCONOL APM® marketed by WITCO
  • PPG-4 myristyl ether PPG-4 lauryl ether
  • PPG-10 ketyl ether PPG-10 ketyl ether
  • CRODALAN LA® cetyl acetate and lanolin acetyl alcohol
  • Oily media composed of mixtures of cosmetic emollients of the type of those appearing in particular in "Cosmetics & Toiletries” / No. 93, page 107-July 1992, are very particularly preferred.
  • Said cosmetic composition can be constituted by said oily medium itself, optionally thickened, or by a single or multiple emulsion "water in oil” or “oil in water”, emulsion in which the oil phase consists of said oily medium optionally thickened .
  • Said composition containing said oily medium optionally thickened present as such or in the form of a single or multiple emulsion "water in oil” or “oil in water”, may also contain other conventional additives for cosmetic formulations such as for example waxes silicones, non-silicone waxes or mineral derivatives.
  • Said composition can also be a solid formulation which can optionally be shaped by molding, such as, for example, deodorants, antiperspirants or lipsticks.
  • Said ester-functional polyorganosiloxanes of formula (I) are very particularly advantageous for the formulation of oily media used in the composition of sun gels, deodorants, or make-up products.
  • Said oily media then contain more than 10%, preferably more than 50% of their weight of volatile silicone oils, media which can optionally be thickened in order to form translucent gels by using, for example, alkyl grafted silicone waxes such as MIRASIL WAX B from Rhône-Poulenc (behenic ester dimethicone).
  • alkyl grafted silicone waxes such as MIRASIL WAX B from Rhône-Poulenc (behenic ester dimethicone).
  • compositions generally contain silicones due to the sensory properties provided by them.
  • the volatile nature of cyclic silicones results in an absence of feeling of cold after deposition on the skin, a non-greasy, non-sticky feel and excellent lubricating behavior.
  • These highly appreciable properties for giving a cosmetically acceptable character to the compositions are transferred to the others constituents of these compositions such as the active constituents associated with silicones.
  • These compositions may also contain other types of silicone such as those known under the names dimethicone copolyol, diphenyl dimethicone, phenyl dimethicone, amodimethicone ... (CTFA dictionary).
  • deodorant or "antiperspirant” compositions either active against perspiration or the formation of unpleasant odors, or modifying the physical appearance of the compositions, depending on whether the final composition is in the form of a liquid, gel or solidified medium. Depending on their physical appearance and depending on the degree of gelation chosen, these compositions can be in the form of sticks, extruded gels, ball applicators, creams, etc.
  • the application to the skin of the gel, of thick or gelled cream or of the solidified medium is made more pleasant when the melting or softening temperature of the gel is close to the temperature of the skin, which results in an effect of slip during application.
  • Common thickening, gelling or solidifying agents are the lithium, sodium, potassium, aluminum, zirconium, cerium ... salts, stearic, hydroxystearic, behenic, montanic acids, esters of carboxylic or hydroxycarboxylic acids in C14-C30 and glycol, polyglycol, glycerol, polyglycerol, C 2 -C 30 aliphatic alcohols, C14-C30 ethers of polyethylene glycol or polypropylene glycol, 0-14-030 aliphatic alcohols, alkyl grafted silicone waxes and in particular waxes behenic ester dimethicone type ...
  • waxes having melting points between 30 ° C and 150 ° C such as beeswax, spermaceti, camauba wax, paraffin , microcrystalline waxes, ceresin, ozokerite.
  • the deodorant or antiperspirant compositions also contain hydroxylated compounds such as ethanol, propylene glycol, glycerol.
  • volatile silicones are generally compatible with alcohols, the same does not apply to non-volatile silicones, the presence of which is desirable for providing emollience, water resistance, anti-transfer or afterglow. If certain non-volatile silicones, such as for example dimethicone copolyols, can be introduced in a limited quantity into media containing high proportions of alcohols, their negative contribution to the sensory profile of the composition makes their use very limited. Said polyorganosiloxanes having an ester function of formula (I) are particularly advantageous because they have the property of being compatible with media rich in alcohols, without harming the sensory profile of the formulation.
  • the polyorganosiloxanes having an ester function of formula (I) improve the cosmetic feel of the composition by providing a feel comparable to that of a mineral oil while benefiting from the specific properties of silicones, such as improving the spreading over the skin or non-comedogenicity.
  • active agents used in the deodorant and / or antiperspirant compositions astringent agents limiting perspiration, antibacterial agents, absorbent compounds, additives controlling unpleasant odors such as bis (pyridine) -2-2 ' disulfide described in EP-A-483428 or the amino acids described in WO 91/11998 or also undecylenic acid.
  • Examples of these compounds are aluminum chloride, aluminum and / or zirconium hydrochloride, dihydrochloride aluminum and / or zirconium, aluminum and / or zirconium trihydrochloride, aluminum and / or zirconium tetrachlorhydrate, aluminum and / or zirconium pentachlorhydrate, aluminum sesquichlorhydrate and / or zirconium, aluminum chlorhydrex, aluminum-zirconium chlorhydrex glycine, aluminum and zirconium octachlorhydrate, aluminum sulfate, zinc sulfate, zirconium and aluminum chlorohydroglycinate, Zirconium hydroxychloride, aluminum and zirconium lactate, aluminum and potassium sulphate, aluminum and sodium chlorohydroxylactate, aluminum bromohydrate, zinc sulfocarbonate, aluminum bromide, zinc phenolsulfonate associated with u alminium sulfate. All these astringent compounds can also be encapsulated or
  • Bactericidal or bacteriostatic compounds can also be added to these deodorant compositions in order to control the proliferation of the microbial flora developing on the body.
  • these compounds mention may be made of chlorhexidine and its derivatives, nisin, trichlosan, trichlorocarban.
  • the persistence of these compounds on the skin can be improved, if desired, by adding from 0 to 10% by weight of polymers such as polydimethylsiloxanes and high viscosity polydimethyldiphenylsiloxanes, preferably greater than 100,000 mPa.s.
  • the astringent compounds are generally present at concentrations of 1% to 70% by weight, preferably from 5 to 50% by weight.
  • the compounds controlling the proliferation of the bacterial flora on the skin can be introduced in concentrations of 0.1 to 10%.
  • volatile compounds such as ethanol, isopropanol, and emollients such as those described in the journal Cosmetics & Toiletries, July 1992, Nj 107, pages 93 et seq.
  • compounds such as alkylmonoglycerides, alkyldiglycerides, diols such as 1-2-propane diol, 1-3, butane diol, polyethylene glycols or polypropylene glycols and their C 2 -C esters
  • compatibilizing agents such as anionic, nonionic, cationic or zwitterionic surfactants can be used.
  • these surfactants those comprising a polyorganosiloxane skeleton are preferred.
  • Said ester-functional polyorganosiloxanes of formula (I) can be used as anti-transfer agents in cosmetic sunscreen compositions.
  • Other silicones may be present.
  • Cyclic volatile silicones such as octamethyl cyclotetrasiloxane, are used for their volatility which allows rapid drying of the composition applied to the skin without resulting in a feeling of cold.
  • they provide the compositions with the desired cosmetic properties by facilitating the spreading of the compositions on the skin and by reducing the oily or oily nature of these compositions, particularly when they are formulated in the form of oil, sun gel or oily continuous phase emulsion.
  • silicones are also used for their good emollient or protective properties for the skin. These properties are described for example in a monograph of PUS Food and Drug Administration (Department of Health and Human Services, Food and Drug Administration, Skin Protectant Drug Products for Over the Counter Human Use, 21 CFR Part 347).
  • the silicones best suited for their emollient properties are polydimethylsiloxanes, silicone copolyols, diphenyidimethicones, phenyltrimethicones, alkylpolysiloxanes, dimethiconols, with viscosities of between 20 and 10,000 mPa.s.
  • Water resistance is essential to ensure the persistence over time of sun protection or UV protection on the skin.
  • the use of high molecular weight polydimethylsiloxane to ensure better persistence on the skin of anti UV active agents is taught in EP-A-197485.
  • polydimethylsiloxane with a degree of polymerization greater than 5000 dimethylsiloxy units are substantially resistant to washing.
  • optimizing the sensory profile often involves the use of other compounds than silicones, in particular if the dry appearance needs to be modified.
  • mineral oils have this unwanted occlusiveness property.
  • the cosmetic compositions protecting against the effects of UV radiation contain organic molecules acting as UV filters, or mineral particles acting as a physical barrier to UV radiation.
  • UV filters or adsorbents are well known in the literature; they are for example described in the article in the journal Cosmetics & Toiletries, Vol 102, March 1987, p21 and following. Mention may be made, for example, of UV filters such as para amino benzoates and their derivatives, salicylates, cinnamates, benzophenones, benzylidene camphor, benzotriazoles and their derivatives and in general the filters cited in Annex 7 to European directive 76/768 / EEC. These UV filters can also be grafted onto a polymer chain, in particular onto a polysiloxane chain.
  • Said ester-functional polyorganosiloxanes of formula (I) can be introduced into the sun protection compositions at concentrations of between 0.5% and 90% by weight of the composition, preferably from 5% to 20% by weight of this composition, in order to improve the feel of these compositions, to facilitate their spreading, to convey ingredients making it possible to increase the persistence of active agents such as anti UV on the skin and to maintain over time the protective activity of the composition deposited on the skin.
  • Said ester-functional polyorganosiloxanes of formula (I) can be combined with gelling or thickening compounds such as the waxes or waxy media described above.
  • the sun protection compositions may include the emollients conventionally used in cosmetics, perfumes, dyes, pigments or lacquers, preservatives, active compounds against oxidation - or free radicals, skin moisturizers and water.
  • Said ester-functional polyorganosiloxanes of formula (I) can also be used in cosmetic make-up compositions to give them an anti-transfer property.
  • Anti-transfer effect makeup compositions may also contain volatile, low viscosity solvents such as isoparaffins containing 8 to 20 carbon atoms, or mixtures thereof, as well as non-volatile silicones such as cyclic or linear polydimethylsiloxanes.
  • These makeup compositions can also contain silicone waxes, the melting point of which is at least greater than 25 ° C. The function of these waxes consists in gelling the organic phase of the composition.
  • silicone waxes examples include lauroyl trimethylolpropane siioxy silicate, risostearyltrimethylolpropane siioxy silicate, alkyl C -C3Q polydimethylsiloxanes, silicone waxes with ester function such as behenic ester dimethicone marketed by the company Rhône-Poulenc.
  • the makeup compositions can also contain other waxes whose melting point is generally of the order of 35 to 120 ° C. such as synthetic waxes, ceresin, paraffins, okozerite, carnauba wax, candelilla wax, cocoa butter, or a mixture thereof.
  • the makeup compositions may also contain powders or more generally dry materials, the particle size of which is generally between 0.02 and 50 microns. These powders can be colored or not (white powder).
  • bismuth oxychloride mica and mica titanium, optionally functionalized silica, synthetic polymers such as Teflon, polyacrylates, polyethylenes or nylon, alumina silicate, bentonites , cellulose, magnesium derivatives such as aluminosilicate, oxide, carbonate, hydroxide, montmorillonites, talc, zinc stearate, titanium oxide, cerium oxide, or mixtures thereof .
  • synthetic polymers such as Teflon, polyacrylates, polyethylenes or nylon, alumina silicate, bentonites , cellulose, magnesium derivatives such as aluminosilicate, oxide, carbonate, hydroxide, montmorillonites, talc, zinc stearate, titanium oxide, cerium oxide, or mixtures thereof .
  • synthetic polymers such as Teflon, polyacrylates, polyethylenes or nylon, alumina silicate, bentonites , cellulose, magnesium derivatives such as aluminosilicate, oxide, carbonate, hydroxide, montmorillonites,
  • organic pigments are generally of aromatic nature such as azo, indigoid, triphenylmethane, anthraquinone, and xanthine and are included under the names D&C and FD&C.
  • Inorganic pigments are generally insoluble metal salts of coloring additives.
  • the pigment / powder weight ratio is between 1/20 and 20/1 depending on the type of makeup formulation. Depending on the type of formulation, the amount of pigment will generally vary between 5 and 50% of the total composition cosmetic. Likewise, the quantity of powder may vary from approximately 10 to 20% of the weight of the composition.
  • the makeup composition may also contain oils, preferably mixtures of oils of different viscosity. Oils with a viscosity between 5 and 100 mPa.s can be used at 25 ° C. For example, oils such as isotridecyl isonononoate, cetyl stearate, Pisodecyl neopentanoate, coco dicaprylate / caprate, isododecanol, or mixtures thereof, may be used. It is also possible to use oils with a viscosity of between 200 and 1,000,000 mPa.s at 25 ° C.
  • oils can generally constitute from 1-20% of the total of the makeup formulation.
  • .3 dosed by gasometry is less than 7.10 mole / Kg.
  • the volatiles are removed at atmospheric pressure for 1 hour at a temperature of 120 ° C. and then for 3 hours at a temperature of 120 ° C. under 20 mbar. Next, residual volatiles are entrained with nitrogen (2 h, 120 ° C., 40 mbar).
  • the number of moles of ⁇ -ethylenic units or impurities is of the order of 0.06 mole / Kg.
  • 3888 g (or approximately 12 moles of -OH units) of the above-prepared ⁇ -hydroxypropylated oil are introduced into a 5000 ml reactor under nitrogen equipped with a double-jacket cooling device.
  • hydrochloric acid content is 3.2% by weight.
  • the elimination continues at room temperature (22-25 ° C) for 8 hours so as to obtain a content of 1.56% by weight.
  • 330 g of sodium hydrogen carbonate (ie 3.9 moles) are then added and the mixture is left to react for 39 hours at room temperature (22-25 ° C.) so as to remove all the hydrochloric acid.
  • the volatiles are removed under reduced pressure for 9 hours at 10 mbar at 100 ° C. It is then filtered on cardboard (quality 616) and 3479.4 g of a clear oil of dynamic viscosity at 25 ° C. of 44 mPa.s are collected.
  • PEG-stearate polyethylene glycol stearate
  • the ingredients from 1 to 4 as well as the preservative are mixed at 70 ° C and added to the water heated to 70 ° C under shearing so as to ensure emulsification.
  • the ingredients 5 to 7 are then added with stirring and the mixture cooled to 40 ° C.
  • the fragrance is added.
  • This emulsion has good properties of resistance to perspiration and of long duration.
  • ingredients from 1 to 8, 10, and 12 are melted under the effect of the temperature and the ingredient 11 is added with stirring.
  • Ingredients 13 to 18 are dispersed in 9 and added to the previous mixture. Homogenization is then carried out, then the mixture is transferred to molds and cooled.
  • mice Mica / titanium 5 bismuth oxychloride 10 Yello pigment 5 aluminum lake 3 Red pigment # 7 calcium lake 4 antioxidant qs preservative qs
  • Lipstick has a well-adapted sensory profile. In particular, it is easy to spread, comfortable to wear.
  • the anti-transfer properties are evaluated by a sensory test carried out by a group of thirty people, consisting of comparing the transfer to the skin, in comparison with a commercial formulation containing no anti-transfer agent of Example 1. After applying the lipstick on the lips and waiting for five minutes, each person proceeded to the application by kissing the upper part of their hand and judging the presence of trace of lipstick. The results are as follows:
  • Parsol MCX 5 isopropyl myristate 5 oleth-25 2 ceteth-20 1 potassium lauryl phosphate 2 glycerol 3 deionized water 62
  • This emulsion sunscreen has good spreading properties on the skin and resistance to water.
  • Waglinol 6016 isopropyl palmitate 7.00 camellia oil Camellia Kissi oil 4.00
  • Rhodicare S Xanthan gum 1 Rhodicare S Xanthan gum 1, 00
  • Myritol 318 Caprylic / Capric Triglyceride 17.5
  • Isostearic acid Isostearic Acid 3.6 PROCEDURE
  • PROCEDURE Disperse RHODICARE S in water, add water, then phase A in phase B with vigorous stirring. Add phase C and phase D. Adjust the pH with citric acid.
  • phase C Add phase C to phase B and mix until a homogeneous mixture is obtained.
  • Viscosity at 25 ° C 100600mPa.s (Brookfield LVT, spindle F, 6 rpm)
  • Example 20 Solar emulsion (oil in water) of SPF equal to 10
  • Disperse and hydrate Rhodicare S in water Add the glycerol and Arlatone 2121. Heat phases A and B separately to 75 ° C. Add phase A to phase B with vigorous stirring and homogenize for one minute. Cool to room temperature under low shear and add the preservative and fragrance.
  • Viscosity at 25 ° C 78,000 mPa.s (Brookfield LVT, sp E, 1,5 rpm)
  • Example 22 Deodorant - transparent gel
  • Example 1 MIRASIL DM 100 Dimethicone 3.0 Isopropyl Palmitate Isopropyl Palmitate 3.0 Tefose 2561 PEG-6 Stearate (and) Ceteth-20 (and) 7.0

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EP98967123A 1997-12-30 1998-12-29 Verwendung von estergruppe enthaltenden silikonen als übertragungswiderstandsmittel in kosmetischen zubereitungen Withdrawn EP1043972A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9716676A FR2773073B1 (fr) 1997-12-30 1997-12-30 Utilisation de silicones a fonctions esters comme agents anti-transfert dans les compositions cosmetiques
FR9716676 1997-12-30
PCT/FR1998/002898 WO1999034775A1 (fr) 1997-12-30 1998-12-29 Utilisation de silicones a fonctions esters comme agents anti-transfert dans les compositions cosmetiques

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EP1043972A1 true EP1043972A1 (de) 2000-10-18

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AU (1) AU4119499A (de)
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FR2827190A1 (fr) * 2001-06-22 2003-01-17 Rhodia Chimie Sa Utilisation d'une huile comprenant un groupement polaire comme aide au depot d'une huile polaire non ionisable
FR2940048B1 (fr) * 2008-12-18 2012-05-11 Oreal Procede de maquillage des matieres keratiniques et ensemble cosmetique pour la mise en oeuvre d'un tel procede.
FR2940047B1 (fr) * 2008-12-18 2012-05-11 Oreal Procede de maquillage et ensemble cosmetique pour la mise en oeuvre d'un tel procede.
KR101904570B1 (ko) 2011-05-17 2018-10-04 모멘티브 퍼포먼스 머티리얼즈 게엠베하 폴리실록산-폴리오가노 블록 공중합체
FR3132432B1 (fr) * 2022-02-07 2025-05-23 Oreal composition solide pour le traitement des fibres kératineuses
WO2023095719A1 (en) * 2021-11-26 2023-06-01 L'oreal Solid composition for treating keratin fibers

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FR2641185B1 (fr) * 1988-12-29 1991-04-05 Oreal Composition de rasage pour la peau a base de polyorganosiloxanes a fonction acyloxyalkyle et procede de mise en oeuvre
FR2653331B1 (fr) * 1989-10-20 1994-05-20 Oreal Utilisation en cosmetique, pour le traitement des cheveux ou de la peau et/ou en dermatologie, d'une dispersion aqueuse a base d'organopolysiloxanes et d'un copolymere acrylate d'ammonium/acrylamide reticule.
GB9506039D0 (en) * 1995-03-24 1995-05-10 Unilever Plc Underarm compositions
FR2733245B1 (fr) * 1995-04-18 1997-05-23 Rhone Poulenc Chimie Utilisation de cires silicones a fonctions esters pour epaissir des milieux huileux

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FR2773073B1 (fr) 2003-01-03

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