AU749034B2

AU749034B2 - Cosmetic composition comprising at least one silicone/ acrylate copolymer and at least one conditioning agent

Info

Publication number: AU749034B2
Application number: AU56486/00A
Authority: AU
Inventors: Christine Dupuis
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1999-09-16
Filing date: 2000-09-05
Publication date: 2002-06-20
Anticipated expiration: 2020-09-05
Also published as: DE60006911T2; ES2211473T3; KR20010039896A; EP1319391A1; AU5648600A; DE60006911T3; PL342562A1; FR2801198B1; DE60006911D1; CA2319929A1; JP2001114656A; BR0004304A; FR2801198A1; ES2211473T5; CN1293030A; ATE255399T1; CA2319929C; JP2004307518A; EP1084694B1; EP1084694A1

Abstract

Cosmetic composition comprises: <??>(a) Silicone/acrylate copolymer produced by radical polymerization of ethylenically unsaturated monomer in presence of silicone derivative with oxyalkylene groups; <??>(b) Conditioner selected from cationic polymers, cationic and amphiphilic surfactants, aliphatic hydrocarbons, fatty alcohols, esters of fatty acids and alcohols, esters of (di)acids and alcohols, ceramides (analogs). <??>Cosmetic composition comprises: <??>(a) a silicone/acrylate copolymer produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a silicone with oxyalkylene groups; and <??>(b) a conditioner selected from cationic polymers, cationic and amphiphilic surfactants, C8-C300 aliphatic hydrocarbons, C8-C30 fatty alcohols, esters of C8-C30 fatty acids and C1-C30 alcohols, esters of C1-C7 (di)acids and C8-C30 alcohols, ceramides and ceramide analogs. <??>Where the cationic polymers are selected from cellulose derivatives, diallyl dimethyl ammonium halide (co)polymers, methacryloyloxyethyl trimethyl ammonium halide (co)polymers, polyquaternary ammonium polymers, polysiloxanes, polysaccharides and polyamidoamines. <??>Independent claims are also included for: <??>(1) An aerosol device containing the above composition and a propellant gas; <??>(2) Cosmetic method comprising application of the above composition.

Description

AUSTRALIA

Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Applicant(s):

L'OREAL

Invention Title: COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE/ACRYLATE COPOLYMER AND AT LEAST ONE CONDITIONING AGENT The following statement is a full description of this invention, including the best method of performing it known to me/us: COSMETIC COMPOSITION COMPRISING AT LEAST ONE SILICONE/ACRYLATE COPOLYMER AND AT LEAST ONE CONDITIONING AGENT The invention relates to a cosmetic composition comprising at least one specific silicone/acrylate copolymer and at least one *..*.conditioning agent. The invention also relates to a cosmetic process, in particular a process for fixing and/or holding the hairstyle by using the said composition, as well as to the use of this composition for the manufacture of a cosmetic formulation intended oooo in particular for holding and/or shaping the hairstyle.

Among hair products, in particular those intended for shaping and/or holding the hairstyle which are most widely available on the cosmetics market, :there may be distinguished the spray compositions essentially consisting of a solution, usually an alcoholic or aqueous solution, and one or more materials.

When the compositions are intended for fixing and/or holding the hairstyle, these materials are generally polymeric resins, whose function is to form welds between the hairs, and these are also known as fixing materials, mixed with various cosmetic adjuvants. These compositions are generally packaged either in a suitable aerosol container placed under 2 pressure with the aid of a propellant, or in a pumpdispenser bottle.

Hair gels and hair mousses which are generally applied to wet hair before blow-drying or setting the hair are also known. A drying or blowdrying operation is then carried out in order to shape and fix the hairstyle. These gels or mousses can also contain polymeric resins.

However, these hair compositions often have 10 the drawback of adversely affecting the cosmetic properties of the hair. Thus, the hair can become coarse and difficult to disentangle, it can lose its pleasant feel and appearance or it may lack body.

Styling compositions are thus sought which afford good cosmetic properties, in particular in terms of disentangling, softness and feel.

In addition, these hair compositions also have the major drawback of giving rise to a powdering effect. For the purposes of the present invention, the term "powdering" means the aptitude of the material obtained, by drying the hair composition, to form a powder after it has been applied to the hair. Needless to say, the powder falls on the user's shoulders or clothing, or it attaches to the comb or the brush, and this is a detrimental effect.

There is thus a need to find cosmetic compositions, in particular for styling the hair, which do not have the set of drawbacks mentioned above, and 3 which in particular fix the hairstyle well, while at the same time affording good cosmetic properties without a powdering effect.

The Applicant has discovered, surprisingly and unexpectedly, that when specific silicone/acrylate copolymers are combined with certain conditioning agents, it is possible to obtain cosmetic compositions which satisfy the requirements expressed above.

One subject of the invention is a cosmetic 10 composition comprising, in a cosmetically acceptable medium, at least one silicone/acrylate copolymer and at least one conditioning agent, the silicone/acrylate copolymer being obtained by radical-mediated polymerization 15 of at least one ethylenically unsaturated monomer in the presence of at least one S" silicone derivative comprising oxyalkylene groups, and the conditioning agent being chosen from the group comprising cationic polymers, cationic or amphiphilic surfactants, organosiloxanes, linear or branched C 8 to C 300 hydrocarbons, linear or branched C 8 to C 30 fatty alcohols, esters of a C 8 to C 30 fatty acid and of a C 1 to C 30 alcohol, esters of a C 1 to C 7 acid or diacid and of a C 8 to C 30 fatty alcohol, and ceramides or ceramide analogues.

4 Another subject of the invention relates to a cosmetic hair process, in particular a process for fixing and/or holding the hairstyle using the said composition.

Yet another subject of the invention relates to the use of this composition for the manufacture of a cosmetic hair formulation which is intended in particular for holding and/or shaping the hairstyle.

The silicone/acrylate copolymers particularly 10 targeted by the present invention are those described in International patent application WO 99/04750. In particular, the copolymer sold by BASF under the name Luviflex Silk is preferred. This polymer is a grafted copolymer of tert-butyl acrylate/methacrylic acid and 15 silicone copolyol.

Preferably, the monomer corresponds to formula (Ia):

X-C-CR

7

=CHR

6 (Ia) 0 in which: X is chosen from the group comprising OH, OM, OR 8

NH

2 NHR and N(R 8 2 M is a cation chosen from Na K Mg",

NH

4 alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium; the radicals R 8 may be identical or different and are chosen from the group comprising hydrogen, linear or branched Ci to C 40 alkyl groups, mono- or polyhydroxylated Ci to C40 alkyl groups, optionally substituted with one or more alkoxy, amino or carboxyl groups, hydroxylated polyethers, and N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, hydroxypropyl, methoxypropyl and S ethoxypropyl groups; 10 R 7 and R 6 are chosen, independently of each other, from the group comprising hydrogen, linear or branched Ci to C8 alkyl groups, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl groups, and CN, COOH and COOM groups.

15 In particular, the monomers of formula (Ia) are acrylic acid and its salts, esters or amides.

The esters may be derivatives of linear Ci to alkyls, of branched C3 to C40 alkyls or of C3 to carboxylic alcohols, of polyfunctional alcohols containing 2 to 8 hydroxyls, such as ethylene glycol, hexylene glycol, glycerol and 1,2,6-hexanetriol, of amino alcohols or of alcohol ethers such as methoxymethanol and ethoxyethanol, or polyalkylene glycols.

The monomers of formula (Ia) may also be chosen from N,N-dialkylaminoalkyl acrylates and methacrylates and N-dialkylaminoalkyl-acrylamides and -methacrylamides, the amide group possibly being unsubstituted, N-alkyl- or N-alkylamino-monosubstituted or N,N-dialkylamino-disubstituted, the alkyl or alkylamino groups being derived from linear C 1 to C 40 or branched C 3 to C 40 carboxylic units.

The monomers of formula (Ia) which can be used may also be substituted compounds derived from acrylic acid or its salts, esters or amides. Mention may be made, for example, of methacrylic acid, ethacrylic acid and 3-cyanoacrylic acid.

10 Other monomers which are particularly suitable are C 1 to C 40 vinyl and allyl esters, linear C 3 to C 40 carboxylic acids or C 3 to C 40 carboxycyclic acids, vinyl or allyl haldides, vinyllactams, preferably vinylpyrrolidone and vinylcaprolactam, heterocyclic 15 compounds substituted with vinyl or allyl groups, preferably vinylpyridine, vinyloxazoline and allylpyridine, N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds, such as styrene or isoprene, and acrylic or methacrylic acid derivatives quaternized with epichlorohydrin.

Other monomers which may finally be mentioned are N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds such as styrene and isoprene, and acrylic or methacrylic acid derivatives quaternized with epichlorohydrin.

Monomers which are most particularly preferred are acrylic, methacrylic and ethacrylic acid; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-thylhexyl and decyl acrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl methacrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl ethacrylate; 2,3-ihydroxypropyl acrylate; 2,3-dihydroxypropyl methacrylate; 2-dihydroxyethyl acrylate; hydroxypropyl 10 acrylate; 2-hydroxyethyl methacrylate; 2-hydroxyethyl

S.

ethacrylate; 2-methoxyethyl acrylate; 2-ethoxyethyl ethacrylate; 2-ethoxyethyl ethacrylate; 2-ethoxypropethyl methacrylate; 2-ethoxyethyl ethacrylate; hydroxypropyl methacrylate; glyceryl monoacrylate; glyceryl monomethacrylate; polyalkylene glycol (meth)acrylates, 15 unsaturated sulphonic acids, acrylamide, methacrylamide, ethacrylamide, N,N-dimethylacrylamide, N-ethylacrylamide, N-ethylmethacrylamide, 1-vinylimidazole, N,N-dimethylaminoethyl (meth)acrylate, maleic acid, fumaric acid, maleic anhydride and its monoesters, crotonic acid, itaconic acid, vinyl ethers, vinylformamide, vinylamine, vinylpyridine, vinylimidazole, vinylfuran, styrene, styryl sulphonate and allyl alcohol, and mixtures thereof.

The monomer can also contain silicon or fluorine atoms or alternatively thio groups. The monomers can be neutralized if they contain acid groups, this being carried out before or after the polymerization, and partially or totally, so as to 8 adjust the solubility or the degree of dispersion in water to the desired level. Agents serving for the neutralization which may be used are mineral bases, such as sodium carbonate, and organic bases such as amino alcohols, for instance alkanolamines such as methanolamine, 2-amino-2-methyl-l-propanol or triethanolamine, and diamines such as lysine.

The monomers can also be quaternized when they contain a basic nitrogen atom. If they contain at 10 least two ethylenic double bonds, the monomers can be partially crosslinked.

The silicone derivatives are in particular the compounds known under the INCI name of dimethicone copolyols or silicone surfactants. Mention 15 may be made of those sold under the brand names Abil® by Goldschmidt, Alkasil" by Rh6ne-Poulenc, silicone Polyol Copolymer by Genesee, Besil by Wacker, Silwet® by OSI or Dow Corning 190® by Dow Corning.

Among the preferred monomers are those which have the formula I below: in which formula

R

2 is chosen from CH 3 and the group

R

3 is chosen from CH 3 and the group R2

R

4 is chosen from hydrogen, CH 3 and the groups R R 6 is an organic C to C 40 group which can contain amino, carboxyl or suiphonated groups, and if c=O, R 6 is the anion of an inorganic acid; the radicals R 1 may be identical or different and are chosen from C 1 to C 2 0 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: [lacuna] Among the preferred silicone derivatives (b) are those which have the formula I below: x ioin which formula -R 2is chosen from CH- 3 and the group 3 2

R

3 is chosen from CH 3 and the group R

R

4 is chosen from hydrogen, CH 3 and the groups 1R11

I

A

1 -41 -CN~ -R 6is a C 1 to C 4 0 organic group which can contain amino, carboxyl or suiphonate groups, and if C=O, R 6 is the anion of an inorganic acid; 11 the radicals R 1 may be identical or different and are chosen from C 1 to C 20 aliphatic hydrocarbons, C 3 to C 20 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: n is an integer between 1 and 6, x and y are integers chosen such that the molecular weight of the polysiloxane is between 300 and 10 30,000, a and b are integers between 0 and 50, and c is 0 or 1.

R

1 is preferably chosen from methyl, ethyl, 15 propyl, butyl, isobutyl, pentyl, isopentyl, hexyl, octyl, decyl, dodecyl and octadecyl groups, cycloaliphatic radicals, in particular cyclohexyl groups, aromatic groups, in particular phenyl or naphthyl groups, and mixtures of aromatic and aliphatic radicals, such as benzyl and phenylethyl, and also tolyl and xylyl.

The preferred radicals R 4 are those having the formula -(CO)c-R 6

R

6 being an alkyl, cycloalkyl or aryl containing 1 to 4 carbon atoms which can contain additional groups such as NH 2 COOH and/or SO 3

H.

12 The preferred radicals R 6 are those for which c=0, which are phosphates or sulphates.

The silicone derivatives which are particularly preferred are those having the general formula below:

JYCH

3 ***The relative proportion of derivative in :the copolymer is generally from 0.1% to 50% and preferably from 1% to 20% by weight.

The preferred copolymers are the watersoluble silicone/acrylate copolymers or those whose dispersibility in water is such that, in a water/ethanol mixture dosed at 50/50 by volume, they are soluble in a proportion of greater than 0.1 g/l and preferably greater than 0.2 g/l.

The composition advantageously comprises, as a relative percentage by weight of the composition, from 0.1% to 20% of silicone/acrylate copolymer and more preferably from 0.5% to 10% of this copolymer.

The composition advantageously comprises, as a relative percentage by weight of the composition, from 0.01% to 20% of conditioning agent and preferably from 0.05% to A conditioning agent which is insoluble in the group comprising poly-cc-olef ins, fluoro oils, plant oils, natural waxes, fluoro waxes, fluoro gums, fatty acid esters, insoluble silicones and amide compounds comprising at least one fatty chain can advantageously be chosen; the said agents can be present in the form of mixtures.

The cationic polymers which can be used as conditioning agents according to the present invention are preferably chosen from polymers comprising primary, secondary, tertiary and/or quaternary amine groups forming part of the polymer chain or directly attached thereto, and having a molecular weight of between 500 and about 5,000,000 and preferably between 1000 and 3,000,000.

When the conditioning agent is a cationic polymer, it is advantageously chosen from the group formed by: cationic cellulose derivatives; dimethyldiallylammonium halide homopolymers and copolymers; methacryloyloxyethyltrimethylammonium halide homopolymers and copolymers; polyquaternary ammonium polymers; vinylpyrrolidone copolymers containing cationic units; cationic polysiloxanes; cationic polysaccharides; polyamidoamines.

14 Among these polymers, mention may be made more particularly of the following cationic polymers: homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the units of the following formulae: -CH-C-

-CH--C-

I 2 or 2 I i I c=o c=o c-==o 0 0 NH .I I I A A (C) I R, N-R X.-N- *in which:

R

3 denotes H or CH 3 A is a linear or branched alkyl group of 1 to 9 6 carbon atoms or a hydroxyalkyl group of 1 to 4 carbon atoms;

R

4 Rs and Re, which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical; RI and R 2 represent hydrogen or an alkyl group containing from 1 to 6 carbon atoms; X denotes a methosulphate anion or a halide such as chloride or bromide.

The copolymers also contain one or more units derived from comonomers which can be chosen from the family of acrylamides, methacrylamides, diaceton acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower alkyls, acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone, and vinyl esters.

Among these compounds, mention may be made of: the copolymer of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate, sold under the name Hercofloc by the company Hercules, 10 the copolymer of acrylamide and of methacryloyloxyethyltrimethylammonium chloride, described in patent application EP-A-080 976 and sold under the name Bina Quat P 100 by the company Ciba Geigy, 15 the copolymer of acrylamide and of methacryloyloxyethyltrimethylammonium methosulphate, sold under the name Reten by the company Hercules, vinylpyrrolidone/dialkylaminoalkyl acrylate or methacrylate copolymers which may or may not be quaternized, such as the products sold under the name "Gafquat" by the company ISP, such as, for example, "Gafquat 734" or "Gafquat 755" or alternatively the products known as "Copolymer 845, 958 and 937". These polymers are described in detail in French patents 2 077 143 and 2 393 573, and the quaternized vinylpyrrolidone/dimethylaminopropylmethacrylamide copolymer, such as the product sold under the name "Gafquat HS 100" by the company ISP; the quaternized polysaccharides described more particularly in US patents 3 589 578 and 4 031 307, such as the product sold under the name Jaguar C 13 S by the company Meyhall; quaternized copolymers of vinylpyrrolidone and of vinylimidazole, such as the products sold under the general name Luviquat by the 10 company BASF.

According to the invention, cationic polymers with film-forming properties are preferably used.

Water-insoluble cationic surfactants can advantageously be chosen from the group consisting of 15 fatty amines and salts thereof, as well as quaternary ammonium salts. The fatty amines are preferably chosen from the group comprising dioctylamine, Sstearyldimethylamine, palmityldimethylamine, oleocetyldimethylamine and amidoamines such as stearylamidoethyldiethylamine, behenylamidopropyldimethylamine, stearylamidopropyldimethylamine, oleylamidopropyldimethylamine and stearylamidoethyldimethylamine.

The cationic surfactant of quaternary ammonium salt type is advantageously chosen from those which have the general formula below: L N X (I) R

R

2 4 in which RI to R 4 which may be identical or different, represent an aliphatic radical comprising from 1 to 22 carbon atoms, or an aromatic, alkoxy, 5 polyoxyalkylene, alkylamide, hydroxyalkyl, aryl or alkylaryl radical comprising from 12 to 22 carbon atoms; X is an anion chosen from the group of halides, phosphates, acetates, lactates and alkylsulphates, or quaternary ammoniumimidazolinium salts of 10 formula (II) below: C H2 -CH,-NHCO-R cH3So4 II) ~in which Rs represents a mixture of alkenyl and/or alkyl radicals comprising from 13 to 21 carbon atoms and tallow fatty acid derivatives, or quaternary diammonium salts of formula

(III):

R 2 (II) in which R 6 denotes an aliphatic radical comprising from 16 to 22 carbon atoms, R 7 Re, R 9

R

10 and R 11 are chosen from hydrogen and an alkyl radical comprising from 1 to 4 carbon atoms, and X is an anion chosen from the group of halides, acetates, phosphates and sulphates.

Among the organosiloxanes used in accordance with the present invention, mention may be made, in a non-limiting manner, of: I. Volatile silicones 10 These have a boiling point of between 60 0

C

and 260 0 C. Among the silicones of this type which are *mentioned are: cyclic silicones of 3 to 7 and preferably a.° 4 to 5 silicon atoms. These are, for example, octamethylcyclotetrasiloxane sold under the name "Volatile Silicone 7207®" by the company Union Carbide or "Silbione 70045 V2®" by the company Rh8ne-Poulenc, decamethylcyclopentasiloxane sold under the name "Volatile Silicone 7158®" by the company Union Carbide, and "Silbione 70045 V5®" by the company Rh6ne-Poulenc, and mixtures thereof.

Mention is also made of cyclopolymers of the dimethylsiloxane/methylalkylsiloxane type, such as "Volatile Silicone FZ 3109®" sold by the company Union Carbide, which is a dimethylsiloxane/methyloctylsiloxane cyclocopolymer; (ii) linear volatile silicones containing 2 to 9 silicon atoms and having a viscosity of less than or equal to 5 x 10 6 m 2 /s at 25 0 C. An example is hexamethyldisiloxane sold under the name "Silbione 70041 V0.65®" by the company Rh8ne-Poulenc. This type of product is described in the article by Todd Byers "Volatile silicone fluids for cosmetics", Cosmetics and Toiletries, Vol. 91, Jan 76, pages 27-32.

10 II. Non-volatile silicones These consist mainly of poly(CI-C 35 alkylsiloxanes, polyarylsiloxanes, poly(Cl-C 3 5 )alkylarylsiloxanes, silicone gums and resins and organomodified polysiloxanes, as well as mixtures 15 thereof.

Among the polyalkylsiloxanes which may be mentioned mainly are linear polydimethylsiloxanes with a viscosity of greater than 5 x 10- 6 m 2 and preferably less than 2.6 m 2 i.e.: containing trimethylsilyl end groups, such as, for example, and in a non-limiting manner, the "Silbione®" oils of the series 70047 sold by the company Rh6ne-Poulenc, the oil "47 V 500,000®" from Rh6ne-Poulenc or certain "Viscasil®" from the company General Electric, containing trihydroxysilyl end groups, such as the oils of the series "48 from the company Rh6ne-Poulenc.

In this class of polyalkylsiloxanes, mention may also be made of the polyalkylsiloxanes sold by the company Goldschmidt under the names "Abilwax 9800®, and "Abilwax 9801®", which are poly(C 1

-C

20 )alkylsiloxanes.

Among the polyalkylarylsiloxanes which may be mentioned are linear and/or branched polydimethylphenylsiloxanes and r' polydimethyldiphenylsiloxanes, with a viscosity from 10-5 m 2 /s to 5 x 10 2 m 2 such as, for example: 10 the oil "Rhodorsil®" 763 from Rh8ne- Poulenc, the "Silbione®" oils of the'series 70641 from-Rh6ne-Poulenc, such as the oils "Silbione 70641 and "Silbione 70641 V200®" from Rh6ne-Poulenc, the product "DC 556®" cosmetic grade fluid from Dow Corning, silicones of the PK series from Bayer, such ~as silicones of the PN and PH series from Bayer, such as "PN 1000®" and "PH 1000", certain oils of the SF series from General Electric, such as "SF 1250®", "SF 1265®", "SF 1154®" and "SF 1023®".

The silicone gums in accordance with the present invention are polydiorganosiloxanes with a high number-average molecular mass of between 200,000 and 1,000,000, which are used alone or as a mixture in a solvent chosen from volatile silicones, 21 polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, methylene chloride, pentane, dodecane, tridecane and tetradecane, or mixtures thereof.

Mention is made, for example, of the compounds having the following structures: poly[(dimethylsiloxane)/- (methylvinylsiloxane)], poly[(dimethylsiloxane)/- 10 (diphenylsiloxane)], poly[(dimethylsiloxane)/- (phenylmethylsiloxane)], 0- poly[(dimethylsiloxane)/- (diphenylsiloxane)/(methylvinylsiloxane)].

15 Mention may be made, for example, in a nonlimiting manner, of the following mixtures: 1) mixtures formed from a polydimethylsiloxane which is hydroxylated at the end of the chain (Dimethiconol according to the CTFA nomenclature) and of a cyclic polydimethylsiloxane (Cyclomethicone according to the CTFA nomenclature), such as the product "Q2 1401®" sold by the company Dow Corning; 2) mixtures formed from a polydimethylsiloxane gum with a cyclic silicone, such as the product "SF 1214 Silicone Fluid®" from General Electric, which is an "SE 30®" gum of MW 500,000 22 dissolved in "SF 1202 Silicone Fluid®" (decamethylcyclopentasiloxane); 3) mixtures of two PDMSs of different viscosities, in particular of a PDMS gum and of a PDMS oil, such as the products "SF 1236®" and "CF 1241®" from the company General Electric. The product "SF 1236®" is the mixture of an "SE 30®" gum defined above

S.

with a viscosity of 20 m 2 /s and of an "SF 96®" oil with S. a viscosity of 5 x 10- 6 m 2 /s (15% "SE 30®" gum and

*S

10 "SF 96®" oil) The product "CF 1241®" is a mixture of an "SE 30®" gum and of a PDMS with a viscosity of 10 3 m 2 /s.

The polyorganosiloxane resins which can be 15 used in accordance with the invention are crosslinked siloxane systems containing the units: R 2 SiO 2 RSiO 3 2 and SiO4/ 2 in which R represents a hydrocarbon-based group containing 1 to 6 carbon atoms or a phenyl group.

Among these products, those particularly preferred are the ones in which R denotes a lower alkyl radical or a phenyl radical.

Among these resins, mention may be made of the product sold under the name "Dow Corning 593" or those sold under the names "Silicone Fluid SS 4230" and "Silicone Fluid SS 4267" by the company General Electric and which are dimethyl/trimethylpolysiloxanes.

The organomodified silicones in accordance with the present invention are silicones as defined above, whose general structure comprises one or more organofunctional groups directly attached to the siloxane chain or attached via a hydrocarbon-based radical.

Mention is made, for example, of silicones comprising: a) perfluoro groups such as trifluoroalkyl groups, such as, for example, those sold by the company General Electric under the names "FF.150 Fluorosilicone 10 Fluid®" or by the company Shin-Etsu under the names "X-22-819®", "X-22-821®" and "X-22-822®"; b) hydroxyacylamino groups such as, for example, those described in patent application EP-A-0 342 834 and in particular the silicone sold by the company Dow Corning under the name "Q2-8413®"; c) thiol groups such as the silicones "X 2-8360®" from the company Dow Corning or "GP 72A®" and "GP 71®" from Genesee; d) substituted or unsubstituted amine groups, such as in "GP 4 Silicone Fluid®" from Genesee, "GP 7100®" from Genesee, "Q2 8220®" from Dow Corning, "AFL 40®" from Union Carbide or the silicone known as "Amodimethicone" in the CTFA dictionary; e) carboxylate groups, such as the products described in patent EP 186 507 from Chisso Corporation; f) hydroxylated groups, such as the polyorganosiloxanes containing a hydroxyalkyl function which are described in patent application FR-85/16334, corresponding to the following formula: R1 SSi--0i O-Si(RI) OSi(RI) 3

OH

in which: 5 the radicals RI, which may be identical or different, are chosen from methyl and phenyl radicals, S. at least 60 mol% of the radicals RI being methyl; the radical R'i is a C 2

-C

18 hydrocarbon-based divalent alkylene chain unit; p is between 1 and 30 inclusive; q is between 1 and 150 inclusive.

Mention may be made most particularly of the product sold by Dow Corning under the name DC 190; S. g) alkoxylated groups, such as in the silicone copolymer "F 755 from SWS Silicones and the products "Abilwax 2428 "Abilwax 2434®" and "Abilwax 2440®" from the company Goldschmidt; h) acyloxyalkyl groups such as, for example, the polyorganopolysiloxanes described in patent application FR-88/17433, corresponding to the following formula: -Si O- i- OH-i-

(I)

I I I L- IpL _q I in which:

R

2 denotes methyl, phenyl, OCOR'' or hydroxyl; only one of the radicals R 2 per silicon atom can be OH;

R'

2 denotes methyl or phenyl; at least 60 mol% of all of the radicals R 2 and R' 2 are methyl; R' denotes C 8

-C

20 alkyl or alkenyl; R denotes a linear or branched C 2

-C

1 8 divalent hydrocarbon-based alkylene; r is between 1 and 120 inclusive; p is between 1 and 30 inclusive; q is 0 or is less than 0.5 p, p q being between 1 and 30 inclusive; the polyorganosiloxanes of formula (II) can contain groups CH 3 -Si-OH in proportions not exceeding 02/2 15% of the sum p q r; i) quaternary ammonium groups, such as in the products "X2 81 08®" and "X2 81 09®" and the product "ABIL K 3270®" from the company Goldschmidt; j) amphoteric or betaine groups, such as in the product sold by the company Goldschmidt under the name "Abil B 9950®"; k) bisulphite groups, such as in the products sold by the company Goldschmidt under the names "Abil S 201®" and "Abil S 255".

The viscosities of the silicones can be determined in particular by ASTM standard D445-97 (viscometry).

When the conditioning agent in the composition according to the invention is a hydrocarbon, it is a linear or branched C 8 -C300 hydrocarbon. Among the hydrocarbons, that are liquid at room temperature, corresponding to this definition, mention may be made in particular of isododecane, 10 isohexadecane and its isomers (such as 2,2,4,4,6,6heptamethylnonane), isoeicosane, isotetracosane and ooo isomers of the said compounds. Isododecane or an isomer thereof is preferably used according to the invention.

When the conditioning agent is a fatty alcohol, it is of the linear or branched, saturated or unsaturated, Cs-C 30 type, and among those mention may be made of 2-butyloctanol, lauryl alcohol, oleyl alcohol, isocetyl alcohol, isostearyl alcohol and behenyl alcohol.

When the conditioning agent is a fatty ester, it may be either an ester of a Cs-C 30 fatty acid and of a Ci-C 30 alcohol or an ester of a Ci-C 7 acid or diacid and of a C 8

-C

30 fatty alcohol. Among these esters, mention may be made of ethyl, isopropyl, 2-ethylhexyl and 2-octyldecyl palmitate, isopropyl, butyl, cetyl and 2-octyldecyl myristate, butyl and hexyl stearate, hexyl and 2-hexyldecyl laurate, isononyl isononanoate and dioctyl malate.

The ceramides or analogues, such as the glycoceramides which can be used in the compositions according to the invention, are known per se and are natural or synthetic molecules which can correspond to the following general formula: R3CHOH-CH--CH 2

OR

2

NH

1

R

1 in which: C=0 R, denotes a linear or branched, saturated or unsaturated alkyl radical derived from C 14

-C

30 fatty *0 acids, it being possible for this radical to be substituted with a hydroxyl group in the a position, or a hydroxyl group in the o position esterified with a saturated or unsaturated C 16

-C

30 fatty acid;

R

2 denotes a hydrogen atom or a (glycosyl)n, (galactosyl)m or sulphogalactosyl radical, in which n is an integer ranging from 1 to 4 and m is an integer ranging from 1 to 8.

R

3 denotes a saturated or unsaturated C15-C 2 6 hydrocarbon-based radical in the position, it being possible for this radical to be substituted with one or more CI-C 14 alkyl radicals; more Ci-Cu4 alkyi radicals; it being understood that, in the case of the natural ceramides or glycoceramides, R 3 can also denote a C 15

-C

26 a-hydroxyalkyl radical, the hydroxyl group optionally being esterified with a C 16

-C

30 a-hydroxy acid.

In the context of the present invention, the preferred ceramides are those described by Downing in Arch. Dermatol., Vol. 123, 1381-1384, 1987, or those described in French patent FR-2 673 179, the structures 10 of which may be as follows: [lacuna] The ceramides more particularly preferred 9* according to the invention are the compounds for which RI denotes a saturated or unsaturated alkyl derived from

C

16

-C

22 fatty acids; R 2 denotes a hydrogen atom; and R 3 denotes a saturated linear C15 radical.

Such compounds are, for example: N-linoleoyldihydrosphingosine, N-oleoyldihydrosphingosine, N-palmitoyldihydrosphingosine, N-stearoyldihydrosphingosine, N-behenoyldihydrosphingosine, or mixtures of these compounds.

Even more preferably, the ceramides for which RI denotes a saturated or unsaturated alkyl radical derived from fatty acids; R 2 denotes a galactosyl or sulphogalactosyl radical; and R 3 denotes a

-CH=CH-(CH

2 12

-CH

3 group, are used.

By way of example, mention may be made of the product consisting of a mixture of these compounds, sold under the trade name Glycocer by the company Waitaki International Biosciences.

The cosmetically acceptable medium preferably consists of water or one or more cosmetically S.acceptable solvents such as alcohols or water/solvent(s) mixtures, the solvents preferably oooo being C 1

-C

4 alcohols.

0 Among these alcohols which may be mentioned are ethanol and isopropanol. Ethanol is particularly **preferred.

oo The composition of the invention can also contain at least one additive chosen from surfactants other than those of the invention, fragrances, screening agents, preserving agents, proteins, vitamins, polymers other than those of the invention, mineral, plant or synthetic oils other than those of the invention, thickening agents and any other additive conventionally used in cosmetic compositions.

Needless to say, a person skilled in the art will take care to select the optional compound(s) to be added to the composition according to the invention such that the advantageous properties intrinsically associated with the composition in accordance with the invention are not, or are not substantially, adversely affected by the addition envisaged.

These compositions may be packaged in various forms, in particular in pump-dispenser bottles or in aerosol containers, in order to ensure application of the composition in vaporized form or in the form of a mousse. Such packaging forms are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating hair. The compositions in accordance with the invention can also o o eeoc *be in the form of creams, gels, emulsions, lotions or 10 waxes.

When the composition according to the *ooo ooo invention is packaged in aerosol form in order to obtain a lacquer or a mousse, it comprises at least one propellant which may be chosen from volatile hydrocarbons such as n-butane, propane, isobutane and pentane, a halogenated hydrocarbon and mixtures thereof. Carbon dioxide, nitrous oxide, dimethyl ether (DME), nitrogen or compressed air can also be used as propellant. Mixtures of propellants can also be used.

Dimethyl ether is preferably used.

The propellant is advantageously present in a concentration of between 5% and 90% by weight relative to the total weight of the composition in the aerosol device, and more particularly at a concentration of between 10% and The compositions in accordance with the invention can be applied to the skin, the nails, the lips, the hair, the eyebrows and the eyelashes.

The compositions in accordance with the invention are particularly suitable for application to dry or wet hair, as styling product.

The invention will be illustrated more fully with the aid of the non-limiting example which follows.

All the percentages are relative percentages by weight with respect to the total weight of the composition, and a.m. means active material.

.0 EXAMPLE: Composition A below is applied to a lock of 5 grams of European natural chestnut hair.

Composition A: Luviflex Silk (1) DC 190(2)

AMP

Ethanol 6% 0.6% qs 100% neutralization qs 100% (1) (t-butyl (2) Silicone/acrylate copolymer sold by BASF acrylate/methacrylic acid/PDMS polyether) Silicone dimethiconol sold by Dow Corning Composition A is applied to natural hair, using a pump-dispenser bottle. After drying, it is observed that the lock feels soft, has a pleasant appearance and produces little powdering on combing.

It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in the art, in Australia or in any other country.

For the purposes of this specification it will be clearly understood that the word "comprising" means "including but not limited to", and that the word "comprises" has a corresponding meaning.

*e

Claims

1. Cosmetic composition comprising, in a cosmetically acceptable medium, at least one silicone/acrylate copolymer and at least one conditioning agent, o* the silicone/acrylate copolymer being obtained by radical-mediated polymerization of at least one ethylenically unsaturated :10 monomer in the presence of at least one silicone derivative comprising oxyalkylene groups, and the conditioning agent being chosen Sfrom the group comprising cationic polymers, cationic or amphiphilic surfactants, organosiloxanes, linear or branched Ce to C 300 hydrocarbons, linear or branched C8 to C 30 fatty alcohols, esters of a Cs to C 30 fatty acid and of a C 1 to C 30 alcohol, esters of a C 1 to C 7 acid or diacid and of a C8 to C 30 fatty alcohol, and ceramides or ceramide analogues.

2. Cosmetic composition according to Claim 1, characterized in that the monomer corresponds to formula (Ia): X-C-CR 7 =CHR 6 (Ia) in which: X is chosen from the group comprising OH, OM, OR 8 NH 2 NHR 8 and N(R )2; M is a cation chosen from Na Mg", NH 4 alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium; the radicals R 8 may be identical or different and are chosen from the group comprising hydrogen, linear or branched Ci to C 40 alkyl groups, 10 mono- or polyhydroxylated Ci to C 40 alkyl groups, optionally substituted with one or more alkoxy, amino or carboxyl groups, hydroxylated polyethers, and N,N-dimethylaminoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, hydroxypropyl, methoxypropyl and ethoxypropyl groups; R 7 and R 6 are chosen, independently of each other, from the group comprising hydrogen, linear or branched Ci to C 8 alkyl groups, methoxy, ethoxy, 2-hydroxyethoxy, 2-methoxyethoxy and 2-ethoxyethyl groups, and CN, COOH and COOM groups.

3. Cosmetic composition according to Claim 1, characterized in that the silicone derivative (b) corresponds to the formula below: in which formula R2is chosen from CH 3 and the group 3 iscoe2rmCH n h ru R 4 is chosen fromhyrn CH 3 and thegruR .r 0 00 0 00 00*e 0000 00 0 0 Sloe *5 C C C V C C C'S. C S 05 CCCV C SC 0 0 eeC e eeoC C, C 5 groups R-17 SO 1 4 4 -R6 is an organic C 1 to C 4 0 group which can contain amino, carboxyl or suiphonate groups, and if c=0, R 6 is the anion of an inorganic acid; the radicals R 1 may be identical or different and are chosen from C 1 to C 20 aliphatic hydrocarbons, C 3 to C 2 0 aliphatic or cycloaliphatic hydrocarbons, and the groups R 5 corresponding to the formula below: IR =4 n is an integer between 1 and 6, x and y are integers chosen such that the molecular weight of the polysiloxane is between 300 and 30,000, a and b are integers between 0 and 50, and c is 0 or 1.

4. Composition according to Claim 1, characterized in that the monomer is chosen from C 1 to C 40 vinyl and allyl esters, linear C 3 to C 40 10 carboxylic acids or C 3 to C 40 carboxycyclic acids, vinyl eo or allyl haldides, vinyllactams, preferably vinylpyrrolidone and vinylcaprolactam, heterocyclic compounds substituted with vinyl or allyl groups, preferably vinylpyridine, vinyloxazoline and 15 allylpyridine, N-vinylimidazoles, diallylamines, vinylidene chloride, carbon-based unsaturated compounds, such as styrene or isoprene, and acrylic or o methacrylic acid derivatives quaternized with epichlorohydrin.

5. Composition according to Claim 1, characterized in that the monomer is chosen from the group comprising acrylic, methacrylic and ethacrylic acid; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl acrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl methacrylate; methyl, ethyl, propyl, n-butyl, isobutyl, t-butyl, 2-ethylhexyl and decyl ethacrylate; 2,3-dihydroxypropyl acrylate; 36 2,3-dihydroxypropyl methacrylate; 2-dihydroxyethyl acrylate; hydroxypropyl acrylate; 2-hydroxyethyl methacrylate; 2-hydroxyethyl ethacrylate; 2-methoxyethyl acrylate; 2-ethoxyethyl methacrylate; 2-ethoxyethyl ethacrylate; hydroxypropyl methacrylate; glyceryl monoacrylate; glyceryl monomethacrylate; polyalkylene glycol (meth)acrylates, unsaturated sulphonic acids, acrylamide, methacrylamide, ethacrylamide, N,N- dimethylacrylamide, N-ethylacrylamide, N- ethylmethacrylamide, 1-vinylimidazole, N,N- dimethylaminoethyl (meth)acrylate, maleic acid, fumaric acid, maleic anhydride and its monoesters, crotonic acid, itaconic acid, vinyl ethers, vinylformamide, vinylamine, vinylpyridine, vinylimidazole, vinylfuran, styrene, styryl 15 sulphonate and allyl alcohol, and mixtures thereof.

6. Composition according to any one of the preceding claims, characterized in that the silicone derivatives are chosen from dimethicone copolyols and silicone surfactants. 20

7. Composition according to any one of the preceding claims, characterized in that it comprises, as a relative percentage by weight, from 0.1% to 20% of silicone/acrylate copolymer.

8. Composition according to Claim 7, characterized in that it comprises, as a relative percentage by weight, from 0.5% to 10% of silicone/acrylate copolymer.

9. Composition according to any one of the preceding claims, characterized in that it comprises, as a relative percentage by weight, from 0.01% to 20% of conditioning agent. Composition according to Claim 9, characterized in that it comprises, as a relative percentage by weight, from 0.05% to 10% of conditioning agent.

H:\suza-net\Keep\Speci\56486-00.1 CLAIMS.doc 16/04/02 37

11. Composition according to any one of the preceding claims, characterized in that the conditioning agent is a cationic polymer chosen from the group comprising: cationic cellulose derivatives; dimethyldiallylammonium halide homopolymers and copolymers; methacryloyloxyethyltrimethyl-ammonium halide homopolymers and copolymers; polyquaternary ammonium polymers; vinylpyrrolidone copolymers containing cationic units; cationic polysiloxanes; cationic polysaccharides; 15 polyamidoamines.

12. Composition according to any one of Claims 1 to 8, characterized in that the conditioning agent is an organosiloxane chosen from poly(Ci-C 35 )alkylsiloxanes, polyarylsiloxanes, poly(C 1 -C 35 )alkylarylsiloxanes, silicone o 20 gums and resins and organomodified polysiloxanes.

13. Composition according to any one of Claims 1 to 10, characterized in that the conditioning agent is a linear or branched C 8 -C 300 hydrocarbon chosen from isododecane, isohexadecane and isomers thereof, isoeicosane, isotetracosane and isomers of the said compounds.

14. Composition according to any one of Claims 1 to characterized in that the conditioning agent is a fatty ester chosen from ethyl, isopropyl, 2-ethylhexyl and 2-octyldecyl palmitate, isopropyl, butyl, cetyl and 2- octyldecyl myristate, butyl and hexyl stearate, hexyl and 2-hexyldecyl laurate, isononyl isononanoate and dioctyl malate H:\suzannet\Keep\Speci\56486-00.1 CLAIMS.doc 16/04/02 38 Composition according to Claim 1, characterized in that the conditioning agent is a ceramide or analogue and corresponds to the formula: R 3 CHOH-CH-CH 2 OR 2 5 NH C=O I RI in which: RI denotes a linear or branched, saturated or unsaturated alkyl radical derived from C 14 -C 30 fatty acids, it being possible for this radical to be substituted with a hydroxyl group in the c position, or a hydroxyl group in the c position esterified with a saturated or unsaturated

15 C 16 -C 30 fatty acid; R 2 denotes a hydrogen atom or a (glycosyl)n, (galactosyl)m or sulphogalactosyl radical, in which n is an integer ranging from 1 to 4 and m is an integer ranging from 1 to 8; 20 R 3 denotes a saturated or unsaturated C 15 -C 26 hydrocarbon-based radical in the a position, it being possible for this radical to be substituted with one or more C 1 -C 14 alkyl radicals; it being understood that, in the case of the natural ceramides or glycoceramides, R 3 can also denote a C 1 5 -C 26 a- hydroxyalkyl radical, the hydroxyl group optionally being esterified with a C 16 -C 30 a-hydroxy acid.

16. Composition according to any one of the preceding claims, characterized in that it also contains at least one additive chosen from surfactants other than those of the invention, fragrances, screening agents, preserving agents, proteins, vitamins, polymers other than H:\suzarmet\Keep\Speci\56 4 8 6 -00.1 CLAIMS.doc 16/04/02 39 those of the invention, mineral, plant or synthetic oils other than those of the invention, and thickeners.

17. Aerosol device formed from a container containing a composition according to any one of the preceding claims and a propellent gas, as well as a means for distributing the composition.

18. Cosmetic process, characterized in that it comprises the application of a composition in accordance with any one of Claims 1 to 16, in particular to the hair.

19. Use of a composition according to any one of Claims 1 to 16, for the manufacture of a cosmetic product, in particular a hair product. 0'0

20. Use of a composition according to any one of Claims 1 to 16, for the skin, the nails, the lips, the 15 hair, the eyebrows and the eyelashes.

21. Cosmetic compositors, aerosol devices containing them or cosmetic processes or uses involving them, substantially as hereinbefore described with reference to oo the example. Dated this 16th day of April 2002 L'OREAL By their Patent Attorneys GRIFFITH HACK Fellows Institute of Patent and Trade Mark Attorneys of Australia H:\suzannet\Keep\Speci\56486-0O.1 CLAIMS.doc 16/04/02