FR2772605A1 - Cosmetic composition, especially for hair treatment - Google Patents

Abstract

Cosmetic composition contains a silicone with at least one substituent containing at least two groups selected from carboxylic acids, carboxylate salts, carboxamides and carboxylate esters, at least one of the groups being a carboxylic acid or carboxylate salt group.

Description

COSMETIC COMPOSITIONS CONTAINING SILICONE
CARBOXYLENE AND METHODS.

The present invention relates to novel cosmetic compositions comprising, in a cosmetically acceptable medium, at least one silicone comprising at least one substituent containing at least two groups, identical or different, chosen from carboxylic acids, amides and esters, at least one these groups being a carboxylic acid and the process for the cosmetic treatment of keratin materials using this composition.

 It is well known that hair which has been sensitized (ie damaged and / or embrittled) to varying degrees under the action of atmospheric agents or under the action of mechanical or chemical treatments, such as coloring, discoloration and / or perms, are often difficult to disentangle and comb, and lack softness.

It has already been advocated in the compositions for washing or caring for keratin materials such as the hair, the use of silicones, in particular cationic silicones, to facilitate disentangling of the hair and to impart to it softness and suppleness. However, the use of cationic silicones for this purpose has various disadvantages. Because of their high affinity for the hair, some of these polymers deposit significantly during repeated uses, and lead to undesirable effects such as an unpleasant, loaded feel. These disadvantages are accentuated in the case of fine hair, which lack of nervousness and volume.

The object of the invention is therefore to propose cosmetic compositions having improved cosmetic properties, in particular with regard to the feel and softness of the hair or the skin.

Now, the Applicant has now found that a particular carboxylic silicone makes it possible to achieve these goals.

The subject of the invention is thus a cosmetic composition, characterized in that it comprises, in a cosmetically acceptable medium, at least one silicone comprising at least one substituent containing at least two groups, identical or different, chosen from carboxylic acids or their salts, amides and esters, at least one of these groups being a carboxylic acid or its salts.

Another subject of the invention relates to a process for the cosmetic treatment of keratin materials, such as the hair, characterized in that it consists in applying to said keratin materials a cosmetic composition according to the invention.

The different objects of the invention will now be detailed. All the meanings and definitions of the compounds used in the present invention given below are valid for all the objects of the invention.

According to the present invention, keratin materials include hair, eyelashes, eyebrows, skin, nails, mucous membranes or scalp and more particularly hair.

According to the present invention, the carboxylic acid groups may be in the free acid form, in the form neutralized with a base.

In all that follows or which precedes, is meant by silicone, in accordance with the general meaning, all polymers or organosilicon oligomers with linear or cyclic structure, branched or crosslinked, of variable molecular weight, obtained by polymerization and / or polycondensation silanes suitably functionalized, and consisting essentially of a repetition of main units in which the silicon atoms are connected to each other by oxygen atoms (siloxane bond -Si-O-Si-), optionally substituted hydrocarbon radicals being directly bonded via a carbon atom to said silicon atoms. The most common hydrocarbon radicals are alkyl radicals, especially C 1 -C 10 and in particular methyl radicals, fluoroalkyl radicals, aryl radicals and in particular phenyl radicals. More particularly, the silicone is a polydimethylsiloxane.

dans laquelle:
W, R2 et R4, identiques ou différents, sont choisis parmi une liaison covalente et un radical alkylène linéaire ou ramifié ayant de 1 à 6 atomes de carbone pouvant comprendre un groupement hydroxyle,
R3 désigne un atome d'hydrogène, un radical alkyle linéaire ou ramifié en C1 c6R
X et X', identiques ou différents, sont choisis parmi les radicaux OM, NRsR6 et
OR7,
M désigne un atome d'hydrogène, un métal alcalin (par exemple Na+, K+), NH4,+ les ammoniums comportant un reste choisi parmi les aminoacides basiques tels que la lysine, I'arginine, la sarcosine, I'ornithine, la citrulline ou bien encore parmi les amino-alcools tels que la monoéthanolamine, la diéthanolamine, la triéthanolamine, la glucamine, la N-méthyl glucamine,
I'amino-3 propanediol-1 ,2. According to the invention, the silicone preferably comprises at least one unit of formula (I) ZRaSiO (3-a) / 2 (1) in which:
Z is a radical of formula (II) below:

in which:
W, R2 and R4, which are identical or different, are chosen from a covalent bond and a linear or branched alkylene radical having from 1 to 6 carbon atoms which may comprise a hydroxyl group,
R3 denotes a hydrogen atom, a linear or branched C1-C6R alkyl radical;
X and X ', which are identical or different, are chosen from the radicals OM, NRsR6 and
OR7,
M denotes a hydrogen atom, an alkali metal (for example Na +, K +), NH4, + the ammoniums containing a residue chosen from basic amino acids such as lysine, arginine, sarcosine, ornithine, citrulline or even among amino-alcohols such as monoethanolamine, diethanolamine, triethanolamine, glucamine, N-methylglucamine,
3-amino-propanediol-1,2.

R5 and R6, which are identical or different, are chosen from hydrogen, linear or branched C1-C6 alkyls or R5 and R6 may together form a 5- or 6-membered heterocycle such as morpholine,
R7 is chosen from linear or branched C1-C30 alkyl radicals,
At least one of the groups X and X 'denotes OM, the radicals R, which are identical or different, are chosen from alkyl radicals, especially C1-C10 and in particular methyl radicals, fluoroalkyl radicals, especially C1-C10 radicals, aryl radicals; in C6-C12 and in particular phenyl, a is chosen from 0, 1 and 2 and preferably 1 or 2.

Preferably, the silicones comprising at least one unit of general formula (I) which correspond to at least one of, and preferably all, the following conditions are used.
W denotes a covalent bond.

R3 denotes a hydrogen atom.

R is methyl.

X and X 'are selected from OM and N5R6
R2 and R4, which are identical or different, are chosen from a covalent bond and a methyl radical.

The other units of the silicone are preferably chosen from those of formula (III): RbSiO (4-b) 12 (III) in which:
R has the same meaning as above and b is 0, 1, 2 or 3 and preferably 2 or 3.

The number of units of formula (I) is preferably between 1 and 20 and more particularly between 1 and 5.

The number of units of formula (III) is preferably between 5 and 150 and more particularly between 10 and 50.

dans laquelle les radicaux R et Z ont la même signification que ci-dessus, les radicaux Z', identiques ou différents, sont choisis parmi les radicaux R et Z, r est un entier compris entre 5 et 150 inclus, s est un entier compris entre 0 et 20 inclus et si s=0, alors au moins un des deux radicaux Z' est égal à Z.For example, the silicones of formula (IV) can be used:

in which the radicals R and Z have the same meaning as above, the radicals Z ', which are identical or different, are chosen from the radicals R and Z, r is an integer between 5 and 150 inclusive, s is an integer understood. between 0 and 20 inclusive and if s = 0, then at least one of the two radicals Z 'is equal to Z.

dans lequel X et X' sont définis ci-dessus, I'un au moins désignant OM. r est de préférence un entier compris entre 20 et 40 inclus, s est un entier compris entre 0 et 10 inclus.More particularly, R denotes the methyl radical, Z denotes the radical

wherein X and X 'are defined above, at least one being OM. r is preferably an integer from 20 to 40 inclusive, s is an integer from 0 to 10 inclusive.

More particularly, X and X 'denote OM or X denotes OM and X' denotes NR5R6.

Preferred silicones according to the invention are polydimethylsiloxanes having at least one succinic anhydride substituent neutralized with alkanolamines such as triethanolamine or hydrolyzed with morpholine.

The silicones according to the invention may be random polymers or block polymers.
Silicones comprising at least one unit of formula (I) are described in particular in US Pat. No. 4,931,062.

The silicones according to the present invention are preferably in the form of O / W emulsions, the average particle size of which is generally between 10 nm and 1 micron.

The number-average molecular mass is preferably between 800 and 30,000.

Such silicones are for example marketed under the name
SLM 23 105 by the company WACKER and under the name DENSODRINe OF by the company BASF.

According to the invention, the silicone or silicones can represent from 0.001% to 15% by weight, preferably from 0.005% to 5% by weight, and still more preferably from 0.01% to 3% by weight, of the total weight of the final composition.

The compositions of the invention may contain active agents having a cosmetic or dermopharmaceutical activity. Examples of active ingredients that may be mentioned include vitamins such as vitamin E and its derivatives, provitamines such as panthenol, humectants, sunscreens, surfactants, preservatives, sequestering agents, softeners, fragrances, colorants, viscosity modifying agents, foam modifiers, foam stabilizers, pearlescent agents, moisturizing agents, anti-dandruff agents, antiseborrhoeic agents, proteins, natural or synthetic oils, silicones different from the carboxylic silicones of the invention, ceramides, pseudoceramides, C16-C40 linear or branched chain fatty acids such as 18-methyl eicosanoic acid, thickeners, plasticizers, hydroxy acids, polymers , electrolytes.

The compositions according to the invention preferably comprise a fixing material. The fixing material consists essentially of at least one fixing polymer. In particular, it is possible to use a fixing polymer chosen from anionic, cationic, amphoteric and nonionic polymers, and mixtures thereof. Such polymers are described in particular in patent application FR 2 747 036, the content of which is totally included by way of reference.

The fixing polymers can be used in solubilized form or in the form of dispersions of solid particles of polymer.

The fixing polymer or polymers are, for example, present in concentrations of between 0.05% and 20% by weight, and preferably in concentrations of between 0.1% and 10% by weight relative to the total weight of the composition.
These additives are present in the composition according to the invention in proportions ranging from 0 to 20% by weight relative to the total weight of the composition. The precise amount of each additive is readily determined by those skilled in the art according to its nature and function.

Of course, those skilled in the art will take care to choose the optional compounds to be added to the composition according to the invention so that the advantageous properties intrinsically attached to the composition according to the invention are not, or substantially not, altered by the proposed addition.

The compositions according to the invention can be used for washing and cleaning keratin materials such as hair and skin. The compositions may for example be used for cleaning or removing makeup from the skin.

The compositions of the invention may be in the form of shampoo, conditioner to be rinsed or not, compositions for permanent, straightening, coloring or bleaching, or in the form of compositions to be applied before or after coloring, discoloration, a permanent or a straightening or between the two stages of a perm or straightening.

The compositions may also be makeup compositions such as foundations, tinted day creams, mascaras, blushers and eyeshadow, lipsticks, nail polish.

More particularly, the compositions may be styling lotions, blow-drying lotions, fixing (lacquer) and styling compositions such as, for example, gels, or foams. The lotions may be packaged in various forms, in particular in vaporizers, pump bottles or in aerosol containers to ensure application of the composition in vaporized form or in the form of foam.

Such forms of packaging are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating the hair.

When the composition according to the invention is packaged in the form of an aerosol in order to obtain a spray or an aerosol foam, it comprises at least one propellant which may be chosen from volatile hydrocarbons such as n-butane and propane. Isobutane, pentane, chlorinated and / or fluorinated hydrocarbons and mixtures thereof. It is also possible to use as propellant carbon dioxide, nitrous oxide, dimethyl ether, nitrogen or compressed air.

According to the invention, the concentration of propellant (s) is generally between 5 and 90% by weight relative to the total weight of the composition and preferably between 10 and 70% by weight. The pressurized compositions in the form of an aerosol foam preferably comprise from 5 to 30% by weight of propellant relative to the total weight of the composition.

Finally, the invention also relates to a process for the cosmetic treatment of human keratin materials, in particular the hair, characterized in that a composition as defined above is applied to said keratin materials.

In all that follows or the above, the percentages expressed are by weight.

The invention will now be more fully illustrated by the following examples which can not be considered as limiting the described embodiments.

In the examples, MA means active ingredient.

EXAMPLE 1
A composition A according to the invention was prepared and compared to two compositions B and C not in accordance with the invention. The three compositions are packaged in a pump bottle.

A panel of testers evaluated the smoothness and the feel of the hair after spraying 1 g of each of these compositions on strands of natural hair of 5 g.

The rating goes from 0 (very bad) to 5 (excellent).

The results are summarized in the table below:

<tb><SEP> In <SEP> gMA <SEP> A <SEP> (Invention) <SEP> B <SEP> C <SEP>
<tb><SEP> (comparative) <SEP> (comparative)
<tb> DENSODRIN <SEP> OF (1) <SEP> 1 <SEP><SEP> ~ <SEP> ~ <SEP>
<tb><SEP> BY22-84o (2) <SEP> - <SEP> 1 <SEP> ~~ <SEP>
<tb><SEP> DC <SEP> 939 <SEP> (3) <SEP> 1
<tb><SEP> pH <SEP> 8 <SEP> 8 <SEP> 8
<tb><SEP> Waterqsp <SEP> 100 <SEP> 100 <SEP> 100
<tb><SEP> Sweetness <SEP> 3.5 <SEP> 2.5 <SEP> 3
<tb><SEP> Touch <SEP> 3 <SEP> 2 <SEP> 2.5
BASF: Polydimethylsiloxane in aqueous emulsion at 20% MA containing at least one morphine monoamidified succinic anhydride substituent of formula: ## STR5 ##

 (2) BY22-840 by Dow Corning: A 35% by weight aqueous emulsion of polydimethyl siloxane with undecylenic acid substituents.

(3) DC 939 from Dow Corning: polydimethylsiloxane containing amino groups (Amodimethicone) sold in emulsion containing 35% of active ingredient
The hair treated with the composition (A) containing the silicone according to the invention are softer and have a better feel than the hair treated with the compositions containing the silicones of the prior art (B and C).

EXAMPLE 2
A styling and hair care gel of the following composition was prepared: Polydimethylsiloxane a, co-succinic neutralized with ammonia
marketed in aqueous emulsion at 23% MA under the
SLM 23105 denomination by the company WACKER 0.5 gMA crosslinked polyacrylic acid (SYNTHALEN K from SIGMA) 1 g - Polyvinylpyrrolidone and vinyl acetate copolymer 1 g
(PVP / VA S 630 from ISP) - Ethanol 8.6 g -Tethanolamine eg -Water qs 100 g
This gel is applied on dry hair. The hair is soft and has a nice touch. The holding of the hairstyle is good.

EXAMPLE 3
A styling foam of the following composition was prepared: hydroxyethylcellulose / diallyl dimethylchloride copolymer
ammonium sold under the name CELQUAT L 200 by
NATIONAL STARCH 0.5 gMA - Methacrylic acid / ethyl acrylate copolymer
sold under the name LUVIMER MAE
by BASF 0,5gMA - Polydimethylsiloxane &alpha;# -succinic neutralized with ammonia
marketed in aqueous emulsion at 23% MA under the
designation SLM 23105 by the company WACKER 0.1 gMA -Electric alcohol 8.6 g - 2-amino-2-methyl-1-propanol qs pH 7.5 -Perfume, dye qs - Demineralised water qs 100g
Aerosol packaging: 90 g of the above composition are packaged in an aerosol container in the presence of 10 g of a ternary mixture of n-butane, isobutane and propane (23/55/22), sold under the name "AEROGAZ" 3.2 N "by society
ELF AQUITAINE
Hair treated with this composition has the same properties as in Example 1.

EXAMPLE 4
A lacquer composition according to the invention was prepared in aerosol of the following composition: - Terpolymer vinyl acetate / p-tert-butyl vinyl benzoate /
Crotonic Acid (65/25/10) 5g - Ethyl Acrylate Terpolymer / Methyl Methacrylate /
methacrylic acid / acrylic acid sold in dispersion
aqueous 25% MA under the denomination
AMERHOLD DR 25 by AMERCHOL 10 gMA - Polydimethylsiloxane a, o-succinic neutralized with ammonia
marketed in aqueous emulsion at 23% MA under the
SLM 23105 name by the company WACKER 2 gMA - Amino-2-methyl-2 propanol-1 0.5 g - Dimethyl ether 30 g - Water qs 100 g
Hair treated with this composition has the same properties as in Example 1.

EXAMPLE 5
A lacquer composition according to the invention was prepared in aerosol of the following composition: - Terpolymer vinyl acetate / p-tert-butyl vinyl benzoate /
Crotonic acid (65/25/10) 7g - Polydimethylsiloxane oc, oesuccinic neutralized with ammonia
marketed in aqueous emulsion at 23% MA under the
SLM 23105 denomination by the company WACKER 1 gMA - Amino-2-methyl-2-propanol-1 0.5 g - Diethyl ether 30 g - Water qs 100 g
Hair treated with this composition has the same properties as in Example 1.

EXAMPLE 6
A fixing spray was prepared in a pump-bottle of the following composition - methacrylic acid terpolymer ethyl acrylate / acrylate
tert-butyl sold under the name LUVIMER 100 P
by BASF 5 g - Polydimethylsiloxane &alpha;# -succinic in aqueous emulsion with
23% MA marketed under the name SLM 23105
by the company WACKER 1 gMA - Ethanol 55 g - Amino-2 methyl-2 propanol-1 0.5 g - Water qs 100 g
Hair treated with this composition has the same properties as in Example 1.

EXAMPLE 7
A shampoo of the following composition was prepared: sodium lauryl ether sulphate (C12 / C14 at 70/30) with
2.2 moles of ethylene oxide in aqueous solution
at 70% of MA Il gMA - Cocobetaine at 32% MA 3gMA - Polydimethylsiloxane containing at least one anhydride substituent
succinic monoamidified by morpholine in emulsion
aqueous 20% MA marketed under the name
DENSODRIN # OF by BASF 2 gMA - Polyethylene glycol distearate 1 g - Coconut acid monoisopropanolamide 2 g - NaCl 2 g - Hydrochloric acid qs pH 7 - Fragrance, preservatives qs - Demineralised water qs 100 g
Shampooing was performed using the composition. Wet hair easily disentangles. The dried hair is easily disentangled, is soft and has an uncharged feel.

EXAMPLE 8
A conditioner of the following composition was prepared: - Hydoxyethylcellulose crosslinked with epichlorohydrin
and quaternized with marketed triethanolamine
under the name CELQUAT SC 240 by
STARCH NATIONAL 1 g - Polydimethylsiloxane &alpha;# - succinic neutralized with ammonia
marketed in aqueous emulsion at 23% MA under the
SLM 23105 denomination by the company WACKER 3 gMA -Hydroxyethylcellulose marketed under the name
NATROSOL 250 HHR by NATIONAL STARCH 1g -NaCl 4g - Mixture of cetylstearyl alcohols and cetylstearyl alcohols
oxyethylenated with 33 moles of ethylene oxide (80/20) 2 g-cetyl alcohol lg -HCl qs pH 5 - water qs 100 g
The composition is applied to washed and dewatered hair. The hair is easily disentangled, the dried hair is soft and has an uncharged feel.

Claims (10)

 1-cosmetic composition, characterized in that it comprises, in a cosmetically acceptable medium, at least one silicone comprising at least one substituent containing at least two groups, identical or different, selected from carboxylic acids or their salts, amides and esters, at least one of these groups being a carboxylic acid or its salts. 2- Composition according to the preceding claim, characterized in that the silicone is an organopolysiloxane comprising per molecule at least one unit of formula (I) ZRaSiO (3-a) 12 (1) in which: Z is a radical of formula (II) below

 in which W, R2 and R4, which are identical or different, are chosen from a covalent bond and a linear or branched alkylene radical having from 1 to 6 carbon atoms which may comprise a hydroxyl group, R3 denotes a hydrogen atom or a linear or branched alkyl radical in C1-C6 X and X ', which are identical or different, are chosen from the radicals OM, NRsR6 and OR7 M is chosen from hydrogen, an alkali metal, NH4, and ammoniums containing a residue chosen from basic amino acids such as lysine, Arginine, sarcosine, ornithine, citrulline or even aminoalcohols such as monoethanolamine, diethanolamine, triethanolamine, glucamine, N-methylglucamine, 3-aminopropanediol-1,2, R5 and R6, which are identical or different, are chosen from hydrogen, linear or branched C1-C6 alkyls or R5 and R6 may together form a 5- or 6-membered heterocycle such as morpholine, R7 is chosen from linear or branched C1-C30 alkyl radicals, At least one of X and X 'is OM, R, which are identical or different, are chosen from alkyl radicals, in particular C1-C10 radicals, fluoroalkyl radicals, especially C1-C10 radicals, and C6-C12 aryl radicals, a is chosen from 0, 1 and 2. 3- Composition according to the preceding claim, characterized in that the silicones comprising at least one unit of general formula (I) meet at least one of, and preferably all, of the following conditions: W denotes a covalent bond R3 denotes a hydrogen atom, R denotes the methyl radical, X and X 'are selected from OM and NR5R6, M is chosen from hydrogen, an alkali metal, NH4, and ammoniums containing a residue chosen from basic amino acids such as lysine, Arginine, sarcosine, ornithine, citrulline or even aminoalcohols such as monoethanolamine, diethanolamine, triethanolamine, glucamine, N-methylglucamine, 3-aminopropanediol-1,2, R5 and R6, which are identical or different, are chosen from hydrogen, linear or branched C1-C6 alkyls or R5 and R6 may together form a 5- or 6-membered heterocycle such as morpholine, R2 and R4, which are identical or different, are chosen from a covalent bond and a methyl radical. 4- Composition according to Claim 2, characterized in that the silicone is chosen from those of formula (IV)

 in which the radicals R and Z have the same meaning as in claim 2, the radicals Z ', which are identical or different, are chosen from the radicals R and Z, r is an integer between 5 and 150 inclusive, s is an integer between 0 and 20 inclusive and if s = 0, then at least one of the two radicals Z 'is equal to Z. 5- Composition according to Claim 4, characterized in that R denotes the methyl radical, Z denotes the radical:

 wherein X and X 'are defined in claim 2, r is an integer from 20 to 40 inclusive, s is an integer from 0 to 10 inclusive. 6. Composition according to claim 5, characterized in that X and X 'denote OM, M being defined according to claim 2. OM and NR5R6 being defined according to claim 2. OM and X 'denotes NR5R6, 7- Composition according to claim 5, characterized in that X designates 7- Composition according to any one of the preceding claims, characterized in that the silicone is present at a concentration of between 0.001% and 10% by weight relative to the total weight of the composition, preferably between 0.005% and 5% by weight. weight and in particular between 0.01% and 3% by weight. 8- Composition according to any one of the preceding claims, characterized in that it comprises a fixing material. 9- Composition according to any one of the preceding claims, characterized in that it is in the form of lotions for setting hair, lotions for blow drying, fixing compositions (lacquers) and styling. 10- A process for the cosmetic treatment of human keratin materials, such as the hair, characterized in that it consists in applying to said keratin materials a cosmetic composition according to one of claims 1 to 9.