WO2000048557A1

WO2000048557A1 - Washing composition for keratinous materials based on water-soluble organic silicon compounds

Info

Publication number: WO2000048557A1
Application number: PCT/FR2000/000250
Authority: WO
Inventors: Henri Samain; Isabelle Rollat-Corvol; Patrice Lerda; Nathalie Garnier
Original assignee: L'oreal
Priority date: 1999-02-18
Filing date: 2000-02-03
Publication date: 2000-08-24
Also published as: FR2789896A1; EP1154750A1; FR2789896B1; KR20010102244A; BR0008338A; AU2302100A; JP2002537238A; CN1336814A; CA2368434A1

Abstract

The invention concerns a composition comprising, in a cosmetically acceptable aqueous medium, at least 0.02 wt. % relative to the composition total weight, one or several water-soluble organic silicon compounds, containing at least two or three silicon atoms, at least a basic chemical function, and at least two hydroxyl or hydrolysable groups per molecule, and at least 4 wt. % relative to the composition total weight, of a detergent surfactant selected among the anionic, non-ionic, amphoteric surfactants and their mixtures. The invention is useful for producing shampoos.

Description

Composition for washing keratin materials based on water-soluble organic silicon compounds.

The present invention relates generally to aqueous compositions for washing keratin materials, and in particular hair and / or skin, comprising water-soluble organic silicon compounds, as well as to washing methods using using these compositions.

It is known that the introduction of cosmetically active organic compounds such as cationic polymers and silicones in detergent cosmetic compositions such as shampoos, gives these compositions properties of disentangling, of providing flexibility and lightness to washed hair. . However, the properties

"styling" characterized by a body maintenance effect and hair discipline, are not sufficient and do not resist washing the hair with a conventional shampoo.

It is also known to use polymeric compounds made partially soluble in water. Thus, certain polymeric compounds can be used in water without adding any co-solvent. In this case, the limitation lies in the fact that these polymeric compounds are eliminated partially, or even completely, by rinsing the hair. Therefore, the effect due to polymeric compounds is very limited after rinsing. In the end, this limits the effect of rinsed treatments

(shampoo, after shampoo), but also reduces the interest of such compositions used in leave-in mode (lacquers, foams, styling lotions, etc.) insofar as the user loses the effect acquired by the treatment when washing his hair. Efforts have therefore been made to find compounds for the formulation of cosmetic compositions which can be used in water and which exhibit a persistence of their effect when the hair is rinsed.

Thus, US Patent No. 4,347,763 (GILLETTE) describes cosmetic compositions comprising an organosiloxane monomer such as an aminoalkylalkoxysilane and an organic titanate in solution in an alcohol.

Patent EP-159,628 describes a composition for perming and fortifying the hair containing an alkyl trialkoxy silane, and patent FR-2,029,696 describes a process for manufacturing a hair fixing product containing an organic resin comprising groups. acids totally or partially neutralized by means of organic silicon compounds containing amino radicals.

The compositions and products described in these documents do not correspond to washing compositions and in particular for washing hair such as shampoos.

There is therefore a need for a detergent cosmetic composition, in particular for washing the hair, which is essentially aqueous and which makes it possible to obtain body effects, for maintaining and texturing very marked hair which is remanent to the washing cycles. while maintaining hair care effects.

The present invention therefore relates to aqueous detergent cosmetic compositions, for washing keratin materials, in particular shampoos, giving the hair a long-lasting styling effect and a pleasant feel, and in particular pronounced body and maintenance and texturing effects, and persistent in the washing cycles.

The applicant has surprisingly noticed that it is possible to formulate compositions for washing keratin materials, in particular shampoos, having the desired properties, by using in these compositions organic silicon compounds, soluble in water, having 1 to 3 silicon atoms, at least one basic chemical group and at least two hydrolyzable or hydroxyl groups per molecule. It has been observed that the application of such compositions allows to obtain a marked styling effect which resists rinsing and washing well. According to the invention, the compositions for washing keratin materials comprise, in a cosmetically acceptable aqueous medium, at least 0.02% by weight relative to the total weight of the composition, of one or more organic silicon compounds soluble in l water, chosen from organosilanes comprising one silicon atom and organosiloxanes comprising two or three silicon atoms, organic silicon compounds further comprising at least one basic chemical function and at least two hydrolysable or hydroxyl groups per molecule, and at least 4% by weight relative to the total weight of the composition of a detergent surfactant chosen from anionic, amphoteric, nonionic surfactants and mixtures thereof.

The organic silicon compounds useful in the compositions of the present invention are chosen from water-soluble organosilanes, comprising one silicon atom and water-soluble organosiloxanes, comprising two or three silicon atoms, preferably two atoms. of silicon. They must also comprise at least one basic chemical function, and preferably only one basic chemical function. The basic chemical function can be any function conferring a basic character on the silicon compound without harming its solubility in water and is preferably an amine function such as a primary, secondary or tertiary amine function. The basic chemical function of the silicon compounds according to the invention may optionally include other functions, such as, for example, another amino function, an acid function or a halogen function.

The organic silicon compounds useful in the compositions of the present invention additionally comprise at least two hydrolyzable or hydroxyl groups per molecule. The hydrolyzable groups are preferably alkoxy, aryloxy or halogen groups. They can also, optionally, include other chemical functions such as acid or amino functions.

The preferred organosilanes according to the invention correspond to the formula:

in which :

R represents a halogen, an OR 'or R' _{j group} ; R ₅ represents a halogen, an OR "or R ' _{2 group} ; Rg represents a halogen, an OR'" or R ' _{3 group} ; and R _j , R ₂ , R ₃ , R ', R ", R'", R, R ' ₂ , R' ₃ represent, independently of each other, a saturated or unsaturated, linear or branched hydrocarbon group, optionally carrying additional chemical groups such as acid or amino groups, R _j , R ₂ , R ', R "and R'" can also denote hydrogen, and at least two of the groups R, R ₅ and R ₆ being different groups R, R ' ₂ and R' ₃ .

Preferably, R _j , R ₂ , R ', R "and R'", R ^* _1? R ' ₂ and R' ₃ represent a C _j to C ₁₂ alkyl group, a C ₆ to C ₁ aryl group, a C _j to C ₆ -alkyl C ₆ to C ₁₄ aryl group, and a C ₆ to C aryl group ₁ -alkyl C to C _g ; and

R ₃ is preferably an alkyl group of C _j to C _12, aryl from C ₆ to C _14, alkyl of C _j to C-aryl from C ₆ to C ₁₄ and aryl from C ₆ to C ₁₄ alkyl C _j to C _g .

The organosiloxanes preferred in the compositions of the present invention can be represented by the formula:

in which :

R _j , R ₂ , R ₃ , R ₅ and R ₆ are defined as above;

R ' ₄ represents a halogen or an ORJ J group;

R ₇ represents a halogen, an OR ₁₀ or R " _{j group} ; R9 represents a halogen, an OR _g , R" ₂ or R ₃ NR _j R _{2 group} ; R " _j , R" ₂ , R ₈ , R ₁₀ and R _π represent a hydrocarbon group, saturated or unsaturated, linear or branched, optionally carrying additional chemical groups such as basic solubilizing groups; R _{] j} , R ₁₀ and R ₈ can also denote hydrogen.

Preferably R " _j , R" ₂ , R _g or R ₁₀ and R _π represent an alkyl group from C _j to C ₁₂ , an aryl group from C ₆ to C ₁ , an alkyl group from C _j to C _{6 -} aryl from C ₆ to C ₁ , and a C ₆ to C ₁ aryl group - C _| to C _g .

At least one of the groups R ₆ , R ₇ and R ₉ denotes a halogen or an OR '", OR ₁₀ or ORg group.

Preferably, the halogen is chlorine.

A particularly preferred class of organic silicon compounds consists of the compounds of formula:

in which the radicals R, identical or different, are chosen pairni the alkyl radicals in C Cg such as methyl, ethyl, propyl, butyl and n is an integer from 1 to 6, preferably from 2 to 4. An organic compound of particularly recommended silicon is γ-aminopropyl triethoxysilane.

The content of organic silicon compounds in the compounds of the invention relative to the total weight of the composition is at least

0.02% by weight, and preferably at least 0.5% and up to 20% by weight. The level of organic silicon compounds according to the invention is determined by usual analysis methods such as NMR spectroscopy of silicon 29 and the proton, and by chromatography.

As indicated above, the detergent compositions according to the invention contain at least one detergent surfactant chosen from anionic, amphoteric and nonionic surfactants having detergent properties.

Among the anionic surfactants, there may be mentioned the alkaline salts, the ammonium salts, the amine salts, the amino alcohol salts, the magnesium salts of the following compounds: alkylsulphates, alkylethersulphates, alkylamidoethersulphates, alkylarylpolyethersulphates, sulphate monoglycerides; alkylsulfonates, alkylamides sulfonates, alkylarylsulfonates, olefins sulfonates, paraffins sulfonates; alkylsulfosuccinates, alkylethersulfosuccinates, alkylamides sulfosuccinates; alkyl sulfosuccinamates; alkyl sulfoacetates; alkylphosphates, alkyl ether phosphates; acylsarcosinates, acylisethionates, N-acyltaurates.

The alkyl or acyl radical of these various compounds generally consists of a carbon chain comprising from 12 to 20 carbon atoms. Among the anionic surfactants, mention may also be made of the salts of fatty acids such as the salts of oleic, ricinoleic, palmitic, stearic acids; coconut oil or hydrogenated coconut oil acids; acyl lactylates, the acyl radical of which contains from 8 to 20 carbon atoms. It is also possible to use surfactants considered to be weakly anionic, such as polyoxyalkylenated alkyl or alkylaryl ether carboxylic acids or their salts, polyoxyalkylenated alkylamido ether carboxylic acids or their salts, uronic alkyl D-galactoside acids or their salts. The nonionic surfactants are more particularly chosen from alcohols or alkylphenols or polyethoxylated, polypropoxylated or polyglycerol fatty acids with a fatty chain containing 8 to 18 carbon atoms, the number of ethylene oxide or oxide groups. propylene being between 2 and 50 and the number of glycerol groups being between 2 and 30.

Mention may also be made of copolymers of ethylene and propylene oxides; condensates of ethylene and propylene oxides on fatty alcohols; polyethoxylated fatty amides preferably having 2 to 30 moles of ethylene oxide; polyglycerol fatty amides preferably comprising 1 to 5 glycerol groups and in particular 1.5 to 4; polyethoxylated fatty amines preferably having 2 to 30 moles of ethylene oxide; fatty acid esters of sorbitan oxyethylene with 2 to 30 moles of ethylene oxide; sucrose fatty acid esters, polyethylene glycol fatty acid esters, alkylpolyglycosides, carbamate or amide derivatives of N-alkyl glucamines, aldobionamides, amine oxides such as the oxides of alkylamines or of N-acylamidopropyl-morpholine.

The preferred amphoteric surfactants are derivatives of aliphatic secondary or tertiary amines, in which the aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and which contains at least one water-soluble anionic group carboxylate, sulfonate, sulfate , phosphate or phosphonate; (C ₈ -C ₂ o) alkyl betaines, sulfobetaines, (Cg-C ₂ o) amidoalkyl (C _j -C ₆ ) betaines alkyl or (C ₈ -C ₂ o) armdoalkyl (C ₁ -C) alkyl ₆ ) sulfobetaines. Among the amine derivatives, mention may be made of the products sold under the name Miranol, as described in patents US-A-2,528,378 and 2,781,354 and classified in the CTFA dictionary, 7th edition, 1997, under the name Disodium Cocoamphodiacetate, Disodium Lauroamphodiacetate, Disodium Capryloamphodiacetate, Disodium Caproamphodiacetate, Disodium Cocoamphodipropionate,

Disodium Lauroamphodipropionate, Disodium Caproamphodipropionate, Disodium Capryloamphodipropionate, Lauroamphodipropionate acid, Cocoamphodipropionate acid.

The surfactants are used in the compositions in accordance with the invention in proportions sufficient to impart a detergent character to the composition, generally at a rate of at least 4% by weight, preferably between 5 and 50% by weight. relative to the total weight of the composition and in particular between 8 and 35%.

The compositions according to the invention have a pH generally between 5 and 12, and more particularly between 6 and 11.

The aqueous medium of the compositions consists either of water or of a mixture of water and of solvent (s) chosen from lower alcohols, alkylene glycols and polyol ethers; the water being present in proportions greater than 20% and preferably greater than 45%.

The compositions according to the invention may also contain viscosity regulating agents, such as electrolytes such as sodium chloride, thickeners such as cellulose derivatives, such as, for example, carboxymethylcellulose, hydroxypropylcellulose, hydroxyethylcellulose , guar gum, hydroxypropylated guar gums, scleroglucans, xanthan gum.

These viscosity regulating agents are used in proportions of up to 15% by weight relative to the total weight of the composition and preferably less than 6%.

The compositions in accordance with the invention may optionally also contain other agents, provided that they do not alter the stability of the compositions, such as cationic surfactants, cationic, anionic, amphoteric or nonionic polymers, or quaternized proteins or not, or oils, waxes, gums or silicone resins.

The polymers, cationic surfactants and quaternized or non-quaternized proteins, silicones, are used in the cosmetic or dermatological compositions, according to the invention, in proportions of between 0.05 and 10% and preferably between 0.1 and 5% relative to the total weight of the composition.

The compositions according to the invention can also contain various adjuvants usually used in cosmetics, such as perfumes, preservatives, sequestrants, foam stabilizers, propellants, dyes, dandruff agents, ceramides, vitamins or pro vitamins, hydroxy acids, acidifying or basifying agents or other adjuvants according to the intended use.

The methods of washing and / or conditioning the hair or the skin consist in applying to them a composition as defined above, this application being followed by rinsing.

The compositions in accordance with the invention can also be used as shower gels for washing the hair and the skin, in which case they are applied to wet skin and hair and rinsed after application.

The examples which follow are intended to illustrate the invention without however being limiting in nature. EXAMPLES

Example 1:

The washing compositions were formulated in Table I below.

TABLE I

A B

(invention) Alkyl (C _{j 2} -C _{j 4} ) ether sulphate oxyethylenated with 2.2 moles of ethylene oxide, sold at 70% of MA 8 MA 8 MA

Lauryl betaine in aqueous solution at 30% MA 2 MA 2 MA

Aminopropyl triethoxysilane (APTES) - 5 0.1N aqueous hydrochloric acid solution at pH = l 1.5 1.5

Water qs 100 100

Assessment of treatment properties

Natural locks of hair were treated with the two compositions, under the following conditions:

1 g of composition per 2.5 g wick Pause time = 10 minutes Rinsing with running water = 20 passages between 2 fingers

Drying = 10 minutes at 60 ° C.

The two wicks are then submitted to a panel of testers to whom the question was asked: "which is the most coated and most textured wick"?

The 10 testers unanimously judged that the locks treated with composition B are more coated and have more texture than the locks treated with composition A. Example 2:

The compositions of Table II below were formulated.

TABLE II

C D

(invention)

Alkyl (C ₁₂ -C ₁₄ ) ether sulphate oxyethylenated to 2.2 moles of ethylene oxide, sold at 70% of MA 10 MA 10 MA

Alkyl polyglucoside in aqueous solution at 53% MA, 5 MA 5 MA sold under the name PLANT ACARE®2000 UP by the company HENKEL

Water qs 100 100

Evaluation of the treating properties:

Wicks were treated as in Example 1.

The two wicks are then submitted to a panel of testers to whom the question was asked: "which is the most coated and the most textured wick"?

The 10 testers unanimously judged that the locks treated with composition D are more coated and have more texture than the locks treated with composition C.

Claims

1. Composition for washing keratin materials, characterized in that it comprises, in a cosmetically acceptable aqueous medium, at least 0.02% by weight relative to the total weight of the composition of at least one organic compound of soluble silicon in water, chosen from silanes comprising a silicon atom and siloxanes comprising two or three silicon atoms, this organic silicon compound further comprising at least one basic chemical function and at least two hydroxyl or hydrolysable groups per molecule, and at least 4% by weight relative to the total weight of the composition of a detergent surfactant chosen from anionic or amphoteric, nonionic surfactants and their mixtures.

2. Composition according to claim 1, characterized in that the organic silicon compound, soluble in water, represents from 0.02 to 20% by weight of the composition.

3. Composition according to claim 1 or 2, characterized in that the basic chemical function of the organic silicon compound is chosen from primary, secondary or tertiary amines.

4. Composition according to any one of claims 1 to 3, characterized in that the hydrolyzable groups are chosen from alkoxy, aryloxy and halogen groups.

5. Composition according to any one of the preceding claims, characterized in that the organic silicon compound (s) are chosen from the compounds of formulas:

in which: R ₄ represents a halogen, an OR 'or R group;

R ₅ represents a halogen, an OR "or R ' _{2 group} ; Rg represents a halogen, an OR'" or R ' _{3 group} ; R _j , R ₂ , R ₃ , R ', R ", R'", R ' _j , R' ₂ , R ' ₃ represent, independently of each other, a saturated or unsaturated, linear or branched hydrocarbon-based group, optionally carrying additional chemical groups, R _j , R ₂ , R ', R "and R""which may also denote hydrogen, at least two groups R, R ₅ and R ₆ being different from groups R, R ' ₂ and R'₃; and

in which: R _j , R ₂ , R, R5 and R ₆ are defined as above;

R ' ₄ represents a halogen or an OR ^ group;

R ₇ represents a halogen, an OR ₁₀ or R 'group,

R represents a halogen, an ORg, R " ₂ or R ₃ NR _j R _{2 group} ;

R " _j , R" ₂ , R _g , R ₁₀ and RJ J represent a hydrocarbon group, saturated or unsaturated, linear or branched, optionally carrying additional chemical groups, the groups R _j , R ₁₀ and R ₈ can also denote hydrogen; at least one of the groups R ₆ , R ₇ and R ₉ denoting a halogen, an OR '"group, OR ₁₀ or ORg.

6. Composition according to claim 5, characterized in that the groups R _j , R ₂ , R ', R, R' ₂ , R ' ₃ , R ", R'", R " _j , R" ₂ , Rg, R ₁₀ and R _n are selected from alkyl of C _j -C _12, aryl from C ₆ AC _1, alkyl of C _j to C-aryl from C ₆ to C _1, and aryl from C ₆ to C ₁ alkyl from C _j to C _g .

7. Composition according to any one of claims 1 to 6, characterized in that the organic silicon compound has the formula:

wherein the radicals R, identical or different, are selected from alkyl C _j -C ₆ alkyl and n is an integer from 1 to 6, preferably 2 to 4.

8. Composition according to claim 7, characterized in that the organic silicon compound is γ-aminopropyl triethoxysilane.

9. Composition according to any one of the preceding claims, characterized in that the detergent surfactant is present in an amount of 5 to 50% by weight, preferably 8 to 35% by weight relative to the total weight of the composition.

10. Composition according to any one of the preceding claims, characterized in that the anionic surfactants are chosen from alkaline salts, magnesium salts, ammonium salts, amine salts or salts of amino alcohols of the following compounds: alkyl sulfates, alkyl ether sulfates, alkylamidoethersulfates, alkylarylpolyethersulfates, monoglycerides sulfates; alkyl sulfonates, alkylamide sulfonates, alkylaryl sulfonates, olefin sulfonates, paraffin sulfonates; alkylsulfosuccinates, alkylethersulfosuccinates, alkylamides sulfosuccinates; alkyl sulfosuccinamates; alkyl sulfoacetates; alkylphosphates, alkyl ether phosphates; acylsarcosinates, acylisethionates, N-acyltaurates; the alkyl or acyl radical of these various compounds being constituted by a carbon chain comprising from 12 to 20 carbon atoms; fatty acid salts of oleic, ricinoleic, palmitic, stearic acids; coconut oil or hydrogenated coconut oil acids; acyl lactylates, the acyl radical of which contains from 8 to 20 carbon atoms; uronic alkyl D-galactoside acids and their salts, polyoxyalkylenated alkyl or alkylaryl ether carboxylic acids or their salts, polyoxyalkylenated alkylamido ether carboxylic acids or their salts.

11. Composition according to any one of claims 1 to 9, characterized in that the nonionic surfactants are chosen from alcohols or alkylphenols or polyethoxylated, polyoxypropylenated or polyglycerole fatty acids, with fatty chain comprising 8 with 18 carbon atoms, the number of ethylene oxide groups, propylene oxide being between 2 and 50 and the number of glycerol groups being between 2 and 30; ethylene propylene oxide copolymers; ethylene propylene oxide condensates on fatty alcohols; polyethoxylated fatty amides; the amides polyglycerol fats; polyethoxylated fatty amines; the oxyethylene sorbitan fatty acid exters; fatty acid esters of sucrose or polyethylene glycol; alkylpolyglycosides; the amide or carbamate derivatives of N-alkylglucamide, the aldobionamides and the amine oxides.

12. Composition according to any one of claims 1 to 9, characterized in that the amphoteric surfactants are chosen from derivatives of aliphatic secondary or tertiary amines, in which the aliphatic radical is a linear or branched chain comprising from 8 to 18 carbon atoms and which contains at least one water-soluble anionic group, carboxylate, sulfonate, sulfate, phosphate, phosphonate; alkyl _(Cg-C20) alkylbetaines, sulfobetaines, (Cg-C ₂₀ alkyl) betaines or (C ₈ -C2o) alkylamido (C _j -C ₆₎ sulfobetaines.

13. Composition according to any one of claims 1 to 12, characterized in that the aqueous medium consists of water or of a mixture of water and a cosmetically acceptable solvent chosen from lower alcohols, alkylene glycols and polyol ethers, water being present in proportions greater than 20%.

14. Composition according to any one of claims 1 to 13, characterized in that the composition additionally contains viscosity regulating agents chosen from electrolytes, hydrotropes or thickening agents present in proportions of up to 15 % by weight relative to the total weight of the composition.

15. Composition according to any one of claims 1 to 14, characterized in that it additionally contains one or more adjuvants chosen from cationic surfactants, anionic or nonionic or cationic or amphoteric polymers, proteins optionally quaternized or an oil, wax, gum or silicone resin.

16. Composition according to any one of claims 1 to

15, characterized in that it contains various cosmetically acceptable adjuvants chosen from perfumes, preservatives, sequestrants, foam synergists, foam stabilizers, acidifying or basifying agents.

17. Use as a shampoo of the composition as defined in any one of claims 1 to 16.

18. Use as a shower gel of the composition as defined in any one of claims 1 to 16.

19. A method for washing keratin materials, characterized in that at least one composition as defined in any one of claims 1 to 16 is applied to these materials, and that after an exposure time, it is rinsed the treated materials with water.