EP0988027A1

EP0988027A1 - Cosmetic composition comprising a functionalised polyorganosiloxane

Info

Publication number: EP0988027A1
Application number: EP98941501A
Authority: EP
Inventors: Paul Branlard; Gérard Mignani; Claudie Willemin; Philippe Olier
Original assignee: Rhodia Chimie SAS
Current assignee: Rhodia Chimie SAS
Priority date: 1997-07-31
Filing date: 1998-07-30
Publication date: 2000-03-29
Also published as: JP2001511437A; AU8985898A; US6509023B1; WO1999006018A1

Abstract

The invention concerns a cosmetic composition comprising at least a functionalised organopolysiloxane of formula (I) or (I'): (R?1)(R2)(R3¿)Si-O-[Si(R4)(Z)-O]¿n?-[Si(R?5)(R6)-O]¿m-Si(R?7)(R8)(R9¿) where in formula (I), m ranges between 0 and 5, n ranges between 0 and 5, at least one of the radicals R?1 and R9¿ representing Z when n is equal to 0; in formula (I'), n ranges between 1 and 5, m ranges between 1 and 5, with n+m equal to at least 3; in formulae (I) and (I') R?1 and R9¿ are identical or different and represent Z or an alkyl radical; R?2, R3, R4, R5, R6, R7 and R8¿ are identical or different and represent an alkyl radical; Z represents a halogenoaliphatic radical, an -X-Y radical, where X represents a polyvalent aliphatic group and Y represents: an aryl radical optionally substituted by an alkyl, aryl group or a halogen atom; an ethylenically unsaturated cycloaliphatic radical optionally substituted by an alkyl group or a halogen atom; a saturated cycloaliphatic radical optionally substituted by a halogen atom; a hydrocarbon heterocyclic radical containing at least one hetereoatom N and/or O and/or S, radical optionally substituted by an alkyl, aryl group or a halogen atom; said symbol Z further capable of representing a phenyl radical when n+m is equal to 0. Said functionalised organotrisiloxane function is used as emollient and/or carrier and/or anti-transfer agent in cosmetic compositions.

Description

COSMETIC COMPOSITION COMPRISING A FUNCTIONALIZED ORGANOPOLYSILOXANE

The subject of the present invention is a cosmetic composition comprising at least one functionalized organopolysiloxane, as well as the use of said organopolysiloxane as an emollient and / or vehicle and / or anti-transfer agent in cosmetic compositions for the skin and / or the hair.

A first subject of the invention consists of a cosmetic composition comprising at least one linear functionalized organopolysiloxane of formula (I)

(R1) (R ² ) (R ³ ) Si - O - [Si (R ⁴ ) (Z) - O] _n - [Si (R5) (R6) - 0] _m - Si (R ⁷ ) (R8) (R9) (I)

or cyclic of formula (I ")

- [Si (R ⁴ ) (Z) - O] _n - [Si (Rδ) (R ^β ) - Q] _m - (I ')

or :

* in formula (I) ° n is an integer or decimal number which can range from 0 to 5, preferably equal to 0 or 1, at least one of the radicals R1 and R ^ representing the symbol Z when n is equal to 0

° m is an integer or decimal number which can range from 0 to 5, preferably equal to 0

* in formula (I ') ° n is an integer or decimal number which can range from 1 to 5, preferably equal to 1

° m is an integer or decimal number which can range from 1 to 5, with n + m at least equal to 3

* in formulas (I) and (D

. the symbols R ^ and R ^ are similar or different and represent the symbol Z or an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, very particularly 1 carbon atom

. the symbols R ² , R ³ , R ⁴ , R ^, Rδ, R ⁷ and R ³ are similar or different and represent an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, very particularly 1 carbon atom. the symbol Z represents,

° a linear or branched, saturated or unsaturated haloaliphatic radical, C5-C20. especially chloro or fluoroaliphatic

° a radical -XY, where X represents a polyvalent saturated or unsaturated, linear or branched aliphatic group containing from 2 to 10 carbon atoms, and Y represents . an aryl radical, preferably Cg, optionally substituted by at least one CjC-8 alkyl or Cg aryl group or a halogen atom (in particular chlorine or fluorine),

. an ethylenically unsaturated C5-C cycloaliphatic radical optionally substituted with at least one C- | -C-8 alkyl group or a halogen atom (in particular chlorine or fluorine),

. a saturated Cs-Cg cycloaliphatic radical substituted by at least one halogen atom (in particular chlorine or fluorine),

. a heterocyclic C 4 -C 9 hydrocarbon radical containing at least one nitrogen and / or oxygen and / or sulfur heteroatom, radical optionally substituted by at least one C 1 -C 6 alkyl or C 6 aryl group or a halogen atom

(in particular chlorine or fluorine), said symbol Z possibly further representing a phenyl radical (directly linked to silicon) when n + m is equal to 0. Said functionalized organopolysiloxanes of formula (I) or (D have in the solubility space from Hansen the following parameters

. ÔD of London interactions ranging from 8 to 21 (J / cm ³ ) ^{1 2}

. 6p of Keesom interactions greater than 0 and up to 25 (J / cm ³ ) ^{1 2}

. OH of hydrogen bonding going from 0 to 23 (J / cm ³ ) ^{1 2} . The three-dimensional solubility space, in which solvents and all organic molecules take place, is defined by CM Hansen in "The three dimensional solubility parameters" J. Paint Technol. 39, 105 (1967); ô, δp and ô _| _ _j represent the partial solubility parameters related respectively to the London dispersion forces, Keesom polarity and hydrogen bonding, knowing that these partial parameters are the components of the global solubility parameter δ, known as

Hildebrand, linked to the volume cohesion of the molecule.

Said polyvalent group X linking the radical Y to the silicon may preferably be a divalent alkanediyl or alkenediyl group containing two carbon atoms, ethylene, methylmethylene, ethenylene, or three carbon atoms, methylethylene, methylethenylene.

As examples of radicals Z, there may be mentioned more particularly the radicals obtained by opening the vinyl double bond of styrene, of methylstyrene, of the dimer of methylstyrene, of limonene, of vinyl pyrrolidone, etc., or of the terminal triple bond of phenylacetylene ... Preferably, said radical Z is a phenyl radical, phenylalkyl in which the alkyl residue contains from 2 to 10 carbon atoms or phenylalkenyl in which the alkenyl residue contains from 2 to 10 atoms of carbon, in particular phenyl (methyl) methyl, phenylethenyl and very particularly phenylethyl. Most preferably the cosmetic composition comprises a mixture of organopolysiloxanes containing mainly an organopolysiloxane with phenylethyl radical, in lesser quantity an organopolysiloxane with phenyl (methyl) methyl radical and in small quantity an organopolysiloxane with phenylethenyl radical. Preferably, said organopolysiloxane is a diorganosiloxane MM of formula (I), in which n and m are equal to 0 and Z is a phenyl radical, in particular diphenyltetramethyldisiloxane, or a linear organotrisiloxane MDM of formula (I) in which n is equal to 1 and m is equal to O, the symbols R ¹ , R ² , R ³ , R ⁴ , R ⁷ , R ³ and R9 are preferably methyl radicals. Very particularly, the invention relates to a cosmetic composition comprising at least one organotrisiloxane with phenylalkyl or phenylalkenyl function of formula (III)

(R ¹ ) (R ² ) (R ³ ) Si - O - Si (R ⁴ ) (Z) - O - Si (R ⁷ ) (R ⁸ ) (R ⁹ ) (III) formula in which. the symbols R ^, R ² , R ³ , R ⁴ , R ⁷ , R ³ and R ⁹ are similar or different and represent an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, all particularly 1 carbon atom. the symbol Z represents a phenyl radical bonded to silicon via a divalent linear or branched alkanediyl or alkenediyl group containing 2 or 3 carbon atoms, preferably 2 carbon atoms. Examples of functionalized organopolyisiloxanes which are particularly advantageous according to the invention are the organotrisiloxanes with phenylalkyl or phenylalkenyl function of formula (a) to (e) below Me ₃ SiO - (Me) Si (CH ₂ -CH ₂ -Ph) O - SiMe ₃ (a)

Me ₃ SiO - (Me) Si [CH (Me) -Ph] O - SiMe ₃ (b) Me ₃ SiO - (Me) Si (CH = CH-Ph) O - SiMe ₃ (c)

Me ₃ SiO - (Me) Si (CH ₂ -CH (Me) -Ph) O - SiMe ₃ (d)

Me ₃ SiO - (Me) Si [CH = C (Me) -Ph] O - SiMe ₃ (e) and the diphenyltetramethyldisiloxane of formula Ph Si (Me) ₂ - O -Si (Me) ₂ Ph

Said organopolysiloxanes of formula (I) or (Y) whose radical (Z) is other than phenyl, can be obtained in known manner by hydrosilylation between at least one hydrogen polyorganosiloxane of formula (II) or (II ')

(R ¹ ) (R ² ) (R ³ ) Si - O - [Si (R ⁴ ) (H) - O] _n - [Si (Rδ) (R6) - 0] _m - Si (R ⁷ ) (R ⁸ ) (R9) (||)

[Si (R ⁴ ) (H) - O] _n - [Si (R5) (R6) - θ] m (II ') formulas in which the symbols R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , n and m have the same definition as that given above, and the compound to terminal vinyl or acetylene unsaturation from which the radical Z is derived, in the presence of a hydrosilylation catalyst such as platinum in particular. This operation can be carried out with a slight excess of one or other of the reactants, generally up to 10 mol% relative to the stoichiometry, at a temperature of the order of 50 ° C to 100 ° C, preferably of the order of 50 ° C. to 80 ° C., in the presence of 5 to 50 parts by mass of platinum (KARSTEDT catalyst for example) per million parts by mass of monomers used. The hydrogenopolyorganosiloxanes preferably used are the hydrogenheptaorganotrisiloxanes MD'M, particularly the hydrogen heptamethyltrisiloxane.

Among the vinyl unsaturated or terminal acetylenic compounds which can be used, there may be mentioned styrene, a methylstyrene, the dimer of a methylstyrene, limonene, vinyl pyrrolidone, phenylacetylene. Preferably, said compound is styrene.

A particular embodiment of the first subject of the invention consists of a cosmetic composition comprising phenymethylheptamethyltrisiloxane of formula Me ₃ Si -O- Si (Me) (Z ¹ ) -O- Si Me ₃ , where Z ¹ represents the function - CH -CH -Ph or a mixture (M) of functionalized heptamethyltrisiloxanes consisting

* for more than 70% by mass, generally for at least 75% by mass of trisiloxane of formula

Me ₃ Si -O- Si (Me) (Z ¹ ) -O- Si Me ₃ , where Z ¹ represents the function -CH ₂ -CH ₂ -Ph

* for less than 25% by mass, generally from 10 to 20% by mass, of trisiloxane of formula

Me ₃ Si -O- Si (Me) (Z ² ) -O- Si Me ₃ , where Z ² represents the function -CH (CH ₃ ) -Ph

* and less than 5% by mass, generally from 0 to 2% by mass of trisiloxane of formula

Me ₃ Si -O- Si (Me) (Z ³ ) -O- Si Me ₃ , where Z ³ represents the function -CH = CH-Ph formulas where Me represents a methyl radical and Ph a phenyl radical.

Said mixture (M) can be obtained by hydrosilylation reaction at a temperature of 50 to 150 ° C, preferably from 50 to 100 ° C, most particularly from 60 to 90 ° C, of hydrogen heptamethyltrisiioxane (reagent SiH) and of styrene (reagent Vi), in the presence of hexamethyldisiloxane as solvent. This hydrosilylation operation is carried out by simultaneous introduction of the two reactants (Vi) and (SiH) into the reaction medium comprising the solvent and a hydrosilylation catalyst, this introduction being carried out in such a way that the respective amounts of the two reactants (Vi ) and (SiH) correspond to a reactive (Vi) / reactive (SiH) molar ratio of more than 0.5 to 1.5, preferably more than 1 to 1, 2, and that at any time during the hydrosilylation reaction, the quantity of reagent (SiH) present, expressed in mass of SiH functions (29 g for 1 function), corresponds to less than 2%, preferably less than 1% of the reaction mass, excluding the mass of solvent. In the definition of the mole of hydrogenheptamethyltrisiloxane, reactive (SiH), the function -SiH is considered as an elementary entity. In the definition of the mole of styrene, reactive (Vi), the gram molecule of styrene is considered as an elementary entity. KARSTEDT hydrosilylation catalyst is used for example at a rate of 1 to 300 parts, preferably from 5 to 100 parts by mass of platinum per million parts by mass of reactants (SiH) and (Vi) used .

The hydrosilylation operation is preferably carried out at atmospheric pressure. The introduction of the reactants (SiH) and (Vi) is preferably carried out by simultaneous casting of the two reactants continuously on the reaction mass comprising the solvent and the catalyst. The duration of the flows is adjusted so as to consume the reagent (Vi) by hydrosilylation as and when it is introduced.

The solvent and unreacted reagents are then removed. Their elimination can be carried out by distillation under vacuum or reduced pressure (for example of the order of 1.013 Pa to 101.300 Pa). This distillation operation is followed by a hydrogenation operation. This can be carried out at a temperature of the order of 25 to 200 ° C, preferably of the order of 50 to 150 ° C, at a hydrogen pressure of the order of 0 to 50 bar, of preferably of the order of 5 to 25 bar, in the presence of a hydrogenation catalyst such as platinum and palladium, in an amount of 0.01 to 5%, preferably from 0.01 to 1% by weight of metal per relative to the mass to be hydrogenated.

The medium is then optionally subjected to an operation for removing products other than heptamethyltrisiloxanes with polarizable functions. This removal operation can be carried out by distillation under vacuum or reduced pressure, for example of the order of 1.013 Pa to 101 300 Pa. The term cosmetic composition or formulation means all cosmetic products or preparations of the type of those or those described in Annex I ("Illustrative list by category of cosmetic products") of European Directive No. 76/768 / EEC of July 27, 1976, known as the Cosmetic Directive.

Cosmetic compositions can be formulated in a large number of types of products for the skin and / or the hair, such as foams, gels (especially styling), masks for the skin or the hair, conditioners, formulations for improving styling or to facilitate combing, detangling of hair, to bring volume or shine, rinsing formulas, lotions and oils for the hands and the body, the products improving the hydration of the skin, the toilet milks, the makeup-removing compositions, the creams or lotions for protection against the sun and the ultraviolet radiation, the milks and creams and / or treating, anti-acne preparations, local analgesics, mascaras, products intended to be applied to the lips or other mucous membranes, sticks, deodorant and antiperspirant products, shaving lotions, bath oils, talcs and many other compositions of the same type.

These cosmetic compositions use a vehicle, or a mixture of several vehicles, present in said compositions at concentrations of between 0.5% and 99.5% approximately, generally between 5 and 90% approximately.

Said functionalized organopolysiloxanes of formula (I) or (Y) present in the cosmetic composition which is the subject of the invention can have several functions within said composition. On the one hand, they can at least partially constitute the vehicle for the natural or synthetic active substances present in said composition; they can thus at least partially replace the usual lipophilic vehicles. On the other hand, they give said composition specific sensory properties and can thus at least partially replace the usual emollients or conditioners, in particular the usual silicone oils. They also confer anti-transfer properties on cosmetic formulations. Said functionalized organopolysiloxanes of formula (I) or (Y) are capable of replacing the organopolysiloxanes of the phenyltrimethicone, octamethyltetramethicone type, etc.

The amounts of functionalized organopolysiloxanes of formula (I) or (Y) present in the cosmetic composition forming the subject of the invention depend on the function sought and the type of cosmetic formulation considered. Those skilled in the art are able to determine these quantities.

Mention may be made as follows, by way of indication, of the quantities by mass of functionalized organopolysiloxanes of formula (I) or () favorably present in the cosmetic composition depending on the desired application.

care products (creams, milks ...) 0.5-5% make-up removing products 1-2% body products 0.5-1.5% make-up products (foundations, powders up to 40% compact , mascaras, eyeshadows, lipsticks ...) hygiene and toilet products (deodorants, 1 -10% antiperspirants, shaving products and hydroalcoholic products) sun products (cream, milk, oil) up to 99%, or even more, preferably 10-40% hair products

(shampoo, after shampoo) up to 5%

(hair care, hair enhancer) up to 10%

The cosmetic compositions forming the subject of the invention also contain other additives and optionally other vehicles or emollients.

As other vehicles, mention may be made of water, alcohols such as ethanol, isopropanol, as well as other solvents such as hydrocarbons, halogenated hydrocarbons, linalool, esters and volatile silicones. The different solvents can be miscible or immiscible with each other.

When the cosmetic compositions are in the form of sprays, tonic lotions, gels or foams, the preferred vehicles include ethanol, volatile silicone derivatives or their mixtures.

Formulations for aerosol sprays and foams may also contain a propellant capable of generating the products in the form of foam or fine, uniform sprays. By way of examples, mention may be made of dimethyl ether, propane, n-butane or isobutane. Next to the vehicle, the cosmetic compositions may contain surfactants; there may be mentioned, by way of examples, anionic surfactants such as

. alkyl esters sulfonates

. alkyl sulfates. alkylamide sulfates

. the salts of saturated or unsaturated fatty acids nonionic surfactants such as

. polyoxyalkylenated alkylphenols

. glucosamides, glucamides; . glycerolamides derived from N-alkylamines

. polyoxyalkylenated C ₃ -C ₂ aliphatic alcohols

. the products resulting from the condensation of ethylene oxide with a hydrophobic compound resulting from the condensation of propylene oxide with propylene glycol,. amine oxides . alkylpolyglycosides and their polyoxyalkylenated derivatives; . amides of fatty acids C ₃ -C ₂ o. ethoxylated fatty acids. amides, amines, ethoxylated amidoamines amphoteric and zwitterionic surfactants such as

* those of betaine type such as

* betaines

* sulfo-betaines

* amidoalkylbetaines • and sulfo-betaines

* the alkylsultaines

* condensation products of fatty acids and protein hydrolysates,

* cocoamphoacetates and cocoamphodiacetates

* alkylamphopropionates or -dipropionates, * amphoteric derivatives of alkylpolyamines

Other emollients can be chosen from alkylmonoglycerides, alkyldiglycerides, triglycerides such as oils extracted from plants and plants (palm, coconut, cottonseed, soybean, sunflower, olive and seed oil. grape, sesame, peanut, castor, argan ...) or oils of marine origin (fish oils, ...), derivatives of these oils such as hydrogenated oils, derivatives of lanolin, mineral oils or paraffinic oils, perhydrosqualane, squalene, diols like 1-2-propanediol, 1-3-butanediol, cetyl alcohol, stearyl alcohol, oleic alcohol, polyethylene glycols or polypropylene glycols, fatty esters such as isopropyl palmitate, ethyl-2-hexyl cocoate, myristyl myristate, esters of lactic acid, stearic acid, behennic acid, isostearic acid, silicone oils including cyclic polydimethylsiloxanes, α-ω hydroxylated polydimethylsiloxanes, α-ω trimethylsilyllated polydimethylsiloxanes, polyorganosiloxanes such as polyalkylmethylsiloxanes, polymethylphenylsiloxanes, polydiphenylsiloxanes, amino derivatives of silicones, commercial waxes MIRMSIL co-oils MISCOsILOsilMR co-ethers -POULENC or DC 190 marketed by DOW CORNING) or mixed silicone derivatives including different types of derivatization (such as mixed polyalkylmethylsiloxanes-silicone copolyether copolymers). Other conditioning agents may also be present.

Among these, mention may be made of those of natural or synthetic origin, such as those known under the generic name CTFA of "Polyquaternium" such as the polymers MIRAPOL A15® or MIRAPOL 550® from the company RHONE-POULENC, cationic derivatives of polysaccharides (cationic derivatives of cellulose, guar or carob), such as cocodimonium hydroxyethyl cellulose, guar hydroxypropyl trimonium chloride, hydroxypropyl guar hydroxypropyl trimonium chloride (JAGUAR C13S®, JAGUAR C162® marketed by RHONE-POULENC), volatile or non-volatile derivatives of silicones such as amodimethicone, cyclomethicones, non-water-soluble and non-volatile organopolysiloxanes such as oils, resins or gums such as diphenyldimethicone gums. To these compositions, it is also possible to add various constituents useful for promoting hydration of the skin (humectants) such as certain carbohydrates (glycerol, sorbitol for example), polyethylene glycol or polypropylene glycol, alkoxylated derivatives of sugars or their derivatives (methyl glucose for example), water-soluble or water-dispersible polymers such as collagen or certain non-allergenic derivatives of marine or vegetable proteins (wheat protein hydrolysates for example).

May also be present thickeners, such as natural hydrocolloids (guar gum, carob, tara ...) or from fermentation processes such as xanthan gum, polysaccharides extracted from algae such as carrageenans, and polycarbohydrate derivatives such as modified celluloses (for example Hydroxyethylcellulose, carboxymethylcellulose, or nonionic derivatives (for example hydroxypropylguar), anionic derivatives (carboxymethylguar) or mixed nonionic / anionic derivatives such as carboxy-hydroxypropyl-guars or nonionic / To these compounds, it is possible to add in combination powders or mineral particles such as calcium carbonate, mineral oxides in the form of powder or in colloidal form (particles of smaller size or of the order of one micrometer, sometimes of a few tens of nanometers) such as titanium dioxide, silica, aluminum salts generally used co even antiperspirants, kaolin, talc, clays and their derivatives ... and all mineral pigments used in make-up formulations.

Preservatives such as methyl, ethyl, propyl and butyl esters of p-hydroxybenzoic acid, sodium benzoate, DMDM hydantoin, or any chemical agent that prevents bacterial growth or mold growth and is included in the list of preservatives admitted and / or provisionally admitted, mentioned in annex VI of the European Directive N ° 76/78 / EEC, traditionally used in cosmetic compositions are generally introduced into these compositions in an amount of 0.01 to 3% by weight. The quantity of these products is generally adjusted to avoid any proliferation of bacteria, molds or yeasts in cosmetic compositions.

To protect the skin or the hair from the aggressions of the sun and UV rays, we can add to these formulations sunscreens which are either chemical compounds strongly absorbing UV radiation like the compounds authorized in the European directive N ° 76/768 / EEC, its annexes and subsequent amendments to this directive or titanium dioxide or cerium oxides in the form of powder or colloidal particles. These powders can optionally be surface-treated to increase the effectiveness of their anti-UV action or to facilitate their incorporation into cosmetic formulations or to inhibit surface photoreactivity.

Perfumes, dyes or pigments may be added to increase the enjoyment when the composition is used by the consumer. Said compositions can also contain fixative resins on keratinous support, at concentrations of between 0.5 and 10%, preferably between 1 and 5%. They are preferably chosen from the following resins: methyl acrylate / acrylamide copolymers, polyvinylmethylether / maleic anhydride copolymers, vinyl acetate / crotonic acid copolymers, octylacrylamide / methyl acrylate / butylaminoethylmethacrylate, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone copolymers / vinyl acetate, polyvinyl alcohols, polyvinyl alcohol / crotonic acid copolymers, polyvinyl alcohol / maleic anhydride copolymers, hydroxypropyl celluloses, hydroypropyl guars, sodium polystyrene sulfonates, polyvinylpyrrolidone / ethyl methacrylate / methacrylic acid, methyl ethyl ethers maleic acid), polyterephthalic ethylene glycol / polyethylene glycol copolymers, polyethylene terephthalate / polyethylene glycol / polyisophthalate copolymers sodium sulfonate, sulfonated polyesters containing polyorganosiloxane units; 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. These cationic resins can also be based on natural water-soluble polymers, such as, for example, cationic polysaccharides such as cationic guar, cationic cellulose, or mixtures thereof. A second subject of the invention consists in the use, as emollient agent and / or vehicle and / or anti-transfer agent in cosmetic compositions, of at least one of said functionalized organopolysiloxanes of formula (I) or (). Specific examples of functionalized organopolysiloxanes of formula (I) or () as well as the concentrations to be used and the nature of the various other additives have already been mentioned above.

The functionalized organopolysiloxanes of formula (I) or (), in particular the organodisiloxanes with phenyl functions and the organotrisiloxanes with phenylalkyl or phenylalkenyl function of formula (III), very particularly phenylethylheptamethyltrisiloxane or mixtures (M) rich in phenylethylheptamethyltrisiloxane, confer on the composition cosmetic specific sensory properties.

They have in particular, as the values below show, a relatively high refractive index, compared to other silicones with a high sensory signal, providing superior properties of brilliance.

The indications below give, for comparison, an estimate of all the sensory properties of said mixture (M), compared with those of a phenyltrimethicone and a dimethicone V 50 (low viscosity).

"0" means "no": not sticky, non-greasy, non-soaping ... depending on the parameter considered "+++" means "very": very slippery, very greasy, very homogeneous, very shiny, very dry depending on the parameter considered ...

The use of functionalized organopolysiloxanes of formula (I and (Y), in particular organodisiloxanes with phenyl functions and organotrisiloxanes with phenylalkyl or phenylalkenyl function of formula (III), makes it possible to impart a silky feel to the skin and makes it possible to reduce touch. oily and sticky that other emollients introduced in the cosmetic formulation can provide.

In capillary application, said functionalized organopolysiloxanes of formula (I) or (D, in particular organodisiloxanes with phenyl functions and organotrisiloxanes with phenylalkyl or phenylalkenyl function of formula (III), are conditioning agents providing properties of shine, disentangling, volume, ease of styling, and improving the appearance of the hair.

In solar application, these are good solubilizers of solar filters. Thus the phenylethyl heptamethyltrisiloxane or the mixture (M) can dissolve more than 200% of its weight of octylmethoxycinnamate (PARSOL MCX from GIVAUDAN).

A third subject of the invention consists of a method for providing sensory and anti-transfer properties to cosmetic compositions, or for improving the sensory and anti-transfer properties of cosmetic compositions, by adding to said cosmetic compositions at least one of the functionalized organopolysiloxanes of formula (I) or (Y).

The present invention further relates to a process for conveying lipophilic active materials in cosmetic compositions, by dissolving said active materials in at least one of the functionalized organopolysiloxanes of formula (I) or (Y). The preferred functionalized organotrisiloxanes of formula (I) or (I '), the amounts of said organopolysiloxanes used, as well as other solvents or additives which may be present, have already been mentioned above.

The following examples are given as an indication.

Example 1

Hydrosilylation of stvrene with heptamethvltrisiloxane

Into a 10-liter reactor, 1803 g (11.12 moles) of hexamethyldisiloxane (HMDS) and 4.15 g of a Karstedt platinum solution containing 11.5% of platinum (0). The reaction mass is brought to 90 ° C. and 4150 g (19.3 moles) of heptamethyltrisiloxane (MD'M) and 2207 g (21, 22 moles) of styrene are poured in simultaneously at 5 hours. Monitoring of the majority species by gas chromatography shows that the reaction is practically quantitative (in% by weight).

The content of free styrene in the reaction mass, at the end of the reaction, represents 88% of the excess of styrene used, which is proof of a very low polymerization. The complement to 100% consists of the reaction product of MD'M by-products (MD'DM and MM "in particular) and styrene. In this table, * X-HMTS has the following meaning

Me ₃ Si -O- Si (Me) (X) -O- Si Me ₃ , where X represents the function -CH ₂ -CH ₂ -Ph

* Y-HMTS has the following meaning

Me ₃ Si -O- Si (Me) (Y) -O- Si Me ₃ , where Y represents the function -CH = CH-Ph

* Z-HMTS has the following meaning Me ₃ Si -O- Si (Me) (Z) -O- Si Me ₃ , where Z represents the function -CH (CH ₃ ) -Ph with Me representing methyl and Ph phenyl.

Distillation

The reaction mass is then concentrated (evaporation of volatiles at 110 ° C. under 20 mbar for 7 hours). 5827 g of a colored product of the following composition are collected (values in% by weight):

Hydrogenation 700g of this colored product is charged to a 1 liter autoclave reactor.

14 g (ie 2% by weight) of a platinum on black catalyst titrating 2% of Pt are introduced. The reaction mass is brought to 100 ° C. under a pressure of 20 bar of hydrogen. After three hours of reaction with stirring, the reaction mass is cooled and brought back to atmospheric pressure. After filtration, 692 g of a colorless product of the following composition are obtained:

After distillation on a column packed with Rashig rings (height = 40 cm), 563.3 g are collected (yield = 81.4%) of a mixture (M) of the following composition:

Example 2

Deodorant in the form of a transparent stick

(1) mixture (M) based on phenylethyl heptamethyltrisiloxane 9% (2) myristyl polypropoxylated ester of propionic acid 70%

(3) propylene glycol 14%

(4) triclosan 0.3%

(5) 6% sodium stearate

(6) qs scent This composition is obtained by preparing a premix of (1), (2) and (3) at around 60 ° C., in which (4) and (5) are dissolved. Leave to cool and add the perfume.

EXAMPLE 3 Mixed dry sun oil (M) based on phenylethyl heptamethyltrisiloxane 27% isopropylpalmitate 25% diisopropyladipate 25%

Mirasil C-DPDM 20% octylmethoxycinnamate 3%

This composition is obtained by simple mixing of its constituents.

Example 4

Hair lotion for the treatment of hair tips mixture (M) based on phenylethyl heptamethyltrisiloxane 5%

Mirasil C-DPDM 90% ethanol 5% This composition is obtained by simple mixing of its constituents.

Example 5

Anti-transfer lipstick

(1) mixture (M) based on phenylethyl heptamethyltrisiloxane 35% (2) 25% pentacyclomethicone

(3) ozokerite 5%

(4) polyisobutene 5%

(5) microcrystalline wax 15% (6) pigments and titanium oxide qs 100% The mixture of (3), (4) and (5) is melted at around 60 ° C. A mixture of (1), (5) and (6) is prepared at around 60 ° C. The two preparations are mixed and added (2).

Example 6

Anti-transfer foundation

(1) mixture (M) based on phenylethyl heptamethyltrisiloxane 20%

(2) pentacyclomethicone 50%

(3) pigments and titanium oxide 20% (4) Parsol MCX de Givaudan 3%

(5) Bentone gel 3% Solubilize (4) in a mixture of (1) and (2). Then we introduce (3) and (5).

Claims

CLAIMS 1) Cosmetic composition comprising at least one linear functionalized organopolysiloxane of formula (I) (R1) (R2) (R3) Si - O - [Si (R4) (Z) - O]n - [Si (Rδ) (R6 ) - 0]m - Si (R7) (R8) (R9) (I) or cyclic of formula (Y) - [Si (R4) (Z) - O]n - [Si (R5) (R6) - O ]m - (Y) where: * in formula (I) ° n is an integer or decimal number which can range from 0 to 5, preferably equal to 0 or 1, at least one of the radicals R1 and R9 representing the symbol Z when n is equal to 0 ° m is an integer or decimal number which can range from 0 to 5, preferably equal 0 * in the formula (Y) ° n is an integer or decimal number which can range from 1 to 5, preferably equal at 1° m is an integer or decimal number that can range from 1 to 5, with n+m at least equal to 3 * in formulas (I) and (Y). the symbols R^ and R9 are similar or different and represent the symbol Z or an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, most particularly 1 carbon atom. the symbols R2, R3, R4, R5, R6, R7 and R8 are similar or different and represent an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, most particularly 1 carbon atom. the symbol Z represents, ° a linear or branched halogenoaliphatic radical, saturated or unsaturated, in Cg-C o, in particular chloro or fluoroaliphatic ° a radical -XY, where to 10 carbon atoms, and Y represents. an aryl radical, preferably Cg, optionally substituted by at least one C1 -C3 alkyl or Cg aryl group or a halogen atom (in particular chlorine or fluorine),. an ethylenically unsaturated C-5-Cg cycloaliphatic radical optionally substituted by at least one C1 -C3 alkyl group or a halogen atom (in particular chlorine or fluorine),. a saturated C5-Cg cycloaliphatic radical substituted by at least one halogen atom (in particular chlorine or fluorine),. a C4-C9 hydrocarbon heterocyclic radical containing at least one heteroatom of nitrogen and/or oxygen and/or sulfur, radical optionally substituted by at least one Cj-Cg alkyl or Cg aryl group or a halogen atom ( in particular chlorine or fluorine), said symbol Z can also represent a phenyl radical (directly linked to silicon) when n+m is equal to 0. 2) Composition according to claim 1), characterized in that the symbol Z is a radical phenyl or a radical obtained by opening the double vinyl bond of styrene, a-methylstyrene, the dimer of a-methylstyrene, limonene, vinyl pyrrolidone, or the terminal triple bond of phenylacetylene. 3) Composition according to claim 1) or 2), characterized in that said radical Z is a phenylalkyl radical whose alkyl radical contains from 2 to 10 carbon atoms or phenylalkenyl whose alkenyl radical contains from 2 to 10 carbon atoms, in particular phenyl(methyl)methyl, phenylethenyl and very particularly phenylethyl. 4) Composition according to any one of claims 1) to 3), characterized in that said functionalized organopolysiloxane is a diorganosiloxane MM of formula (I), in which n and m are equal to 0 and Z is a phenyl radical, or a linear organotrisiloxane MDM of formula (I) in which n is equal to 1 and m is equal to 0, the symbols R1, R2, R3, R4, R7, R8 and R9 preferably being methyl radicals. 5) Composition according to any one of claims 1) to 4), characterized in that said functionalized organopolysiloxane is an organotrisiloxane with phenylalkyl or phenylalkenyl function of formula (III)

(R1) (R ² ) (R ³ ) Si - O - Si (R ⁴ ) (Z) - O - Si (R ⁷ ) (R ⁸ ) (R ⁹ ) (III) formula in which

. the symbols R ¹ , R ² , R ³ , R ⁴ , R ⁷ , R ⁸ and R ⁹ are similar or different and represent an alkyl radical containing from 1 to 8 carbon atoms, preferably 1 or 2 carbon atoms, all particularly 1 carbon atom

. the symbol Z represents a phenyl radical linked to silicon via a bivalent linear or branched alkanediyl or alkenediyl group containing 2 or 3 carbon atoms, preferably 2 carbon atoms. 6) Composition according to any one of claims 1) to 5), characterized in that said functionalized organopolysiloxane is chosen from:

* organotrisiloxanes with a phenylalkyl or phenylalkenyl function of formula (a) to (e) below

Me ₃ SiO - (Me) Si (CH ₂ -CH ₂ -Ph) O - SiMe ₃ (a)

Me ₃ SiO - (Me) Si [CH(Me)-Ph] O - SiMe ₃ (b)

Me ₃ SiO - (Me) Si (CH=CH-Ph) O - SiMe ₃ (c)

Me ₃ SiO - (Me) Si (CH ₂ -CH(Me)-Ph) O - SiMe ₃ (d) Me ₃ SiO - (Me) Si [CH=C(Me)-Ph] O - SiMe ₃ (e) )

* diphenyltetramethyldisiloxane of formula Ph Si (Me) ₂ - O -Si (Me) ₂ Ph

7) Composition according to any one of claims 1) to 6), characterized in that said functionalized polyorganosiloxane comprises a mixture (M) of functionalized heptamethyltrisiloxanes consisting

* for more than 70% by weight, generally for at least 75% by weight of trisiloxane of formula

* for less than 25% by weight, generally 10 to 20% by weight, of trisiloxane of formula

* and less than 5% by weight, generally 0 to 2% by weight of trisiloxane of formula

Me ₃ Si -O- Si (Me) (Z ³ ) -O- Si Me ₃ , where Z ³ represents the function -CH=CH-Ph formulas where Me represents a methyl radical and Ph a phenyl radical.

8) Cosmetic composition according to any one of claims 1) to 7), characterized in that said functionalized organopolysiloxane represents from 0.5 to 99% of the weight of said composition.

9) Use, as an emollient agent and/or vehicle and/or anti-transfer agent in cosmetic compositions, of at least one functionalized organopolysiloxane as defined in any one of claims 1) to 7).

10) Use according to claim 9), characterized in that said functionalized organopolysiloxane is used at a rate of 0.5 to 99% of the weight of said cosmetic composition. 11) Process for providing sensory and anti-transfer properties to cosmetic compositions, or for improving the sensory and anti-transfer properties of cosmetic compositions, by adding to said cosmetic compositions at least one functionalized organopolysiloxane as defined in one any of claims 1) to 7).

12) Process for conveying lipophilic active materials in cosmetic compositions, by dissolving said active materials in at least one functionalized organopolysiloxane as defined in any one of claims 1) to 7).

13) Method according to claim 11) or 12), characterized in that said functionalized organopolysiloxane is used at a rate of 0.5 to 99% of the weight of said cosmetic composition.