AU2302100A

AU2302100A - Washing composition for keratinous materials based on water-soluble organic silicon compounds

Info

Publication number: AU2302100A
Application number: AU23021/00A
Authority: AU
Inventors: Nathalie Garnier; Patrice Lerda; Isabelle Rollat-Corvol; Henri Samain
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 1999-02-18
Filing date: 2000-02-03
Publication date: 2000-09-04
Also published as: CA2368434A1; KR20010102244A; WO2000048557A1; FR2789896B1; CN1336814A; EP1154750A1; JP2002537238A; BR0008338A; FR2789896A1

Description

WO 00/48557 PCT/FROO/00250 Composition for washing keratin materials, based on water-soluble organosilicon compounds The present invention relates in general to aqueous 5 compositions for washing keratin materials, and in particular the hair and/or the skin, comprising water soluble organosilicon compounds, and also to washing processes using these compositions. 10 It is known that introducing cosmetically active organic compounds such as cationic polymers and silicones into detergent cosmetic compositions such as shampoos gives these compositions disentangling properties and provides washed hair with softness and lightness. However, the 15 "styling" properties characterized by an effect of maintaining volume and hold on the hair are insufficient and do not withstand the hair being washed with a standard shampoo. 20 It is also known practice to use polymer compositions which have been made partially water-soluble. Thus, certain polymer compounds may be used in water without adding any co-solvent. In this case, the limitation lies in the fact that these polymer compounds are partially, 25 or even totally, removed by rinsing the hair. Consequently, the effect due to the polymer compounds is very limited after rinsing. Ultimately, this limits the effect of rinse-out treatments (shampooing, conditioning), but also reduces the advantage of such 30 compositions used in leave-in mode (lacquers, mousses, hairsetting lotions, etc.) since the user loses the effect acquired by the treatment when he washes his hair. Efforts have thus been devoted to finding compounds for 35 formulating cosmetic compositions which may be used in water and which show remanence of their effect when the -2 hair is rinsed. Thus, US patent No. 4 344 763 (Gillette) describes cosmetic compositions comprising an organosiloxane 5 monomer such as an aminoalkylalkoxysilane and an organic titanate dissolved in an alcohol. Patent EP-159 628 describes a permanent-waving and strengthening composition for the hair containing an 10 alkyltrialkoxysilane, and patent FR-2 029 696 describes a process for manufacturing a hair-fixing product containing an organic resin comprising acid groups that are totally or partially neutralized with organosilicon compounds containing amino radicals. 15 The compositions and products described in these documents do not correspond to washing compositions, and in particular compositions for washing the hair such as shampoos. 20 There is thus a need for a detergent cosmetic composition, in particular for washing the hair, which is essentially aqueous and which produces very pronounced volumizing, hold and texturing effects on the hair which 25 are resistant to washing cycles, while at the same time maintaining care effects on the hair. One subject of the present invention is thus aqueous detergent cosmetic compositions for washing keratin 30 materials, in particular shampoos, which give the hair a long-lasting styling effect and a pleasant feel, and in particular pronounced volumizing, hold and texturing effects which are resistant to washing cycles. 35 The Applicant has noted, surprisingly, that it is possible to formulate compositions for washing keratin - 3 materials, in particular shampoos, which have the desired properties, by using in these compositions water-soluble organosilicon compounds comprising 1 to 3 silicon atoms, at least one basic chemical group and at least two 5 hydrolyzable or hydroxyl groups per molecule. It has been found that applying such compositions produces a pronounced styling effect which withstands rinsing and washing. 10 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 water 15 soluble organosilicon compounds chosen from organosilanes comprising one silicon atom and organosiloxanes comprising two or three silicon atoms, the organosilicon compounds also comprising at least one basic chemical function and at least two hydrolyzable or hydroxyl groups 20 per molecule, and at least 4% by weight, relative to the total weight of the composition, of a detergent surfactant chosen from anionic, amphoteric and nonionic surfactants, and mixtures thereof. 25 The organosilicon compounds that are useful in the compositions of the present invention are chosen from water-soluble organosilanes comprising a silicon atom and water-soluble organosiloxanes comprising two or three silicon atoms, preferably two silicon atoms. They must 30 also comprise at least one basic chemical function, and preferably only one basic chemical function. The basic chemical function may be any function which gives the silicon compound a basic nature without harming its solubility in water and is preferably an amine function 35 such as a primary, secondary or tertiary amine function. The basic chemical function of the silicon compounds - 4 according to the invention may optionally comprise other functions such as, for example, another amine function, an acid function or a halogen function. 5 The organosilicon compounds that are useful in the compositions of the present invention also comprise at least two hydrolyzable or hydroxyl groups per molecule. The hydrolyzable groups are preferably alkoxy, aryloxy or halogen groups. They may also optionally comprise other 10 chemical functions such as acid or amine functions. The organosilanes that are preferred according to the invention correspond to the formula: R\ R4 15 N - R3 - Si-R R- R R2 R6 in which:

R

4 represents a halogen or a group OR' or R' 1 ; RK represents a halogen or a group OR" or R' 2 ; RK represents a halogen or a group OR"' or R',; 20 and R 1 , R 2 , R3, R', R", R"', R' 1 , R' 2 and R' 3 represent, independently of each other, a saturated or unsaturated, linear or branched hydrocarbon-based group optionally bearing additional chemical groups such as acid or amine groups, R 1 , R 2 , R', R" and R"' also possibly 25 denoting hydrogen, and at least two of the groups R 4 , R. and R 6 being other than groups R' 1 , R' 2 and R'_. Preferably, R 1 , R 2 , R', R" and R"', R' 1 , R' 2 and R' 3 30 represent a C1 to C12 alkyl group, a CE to C14 aryl group, a (C, to C.) alkyl (CG to C14) aryl group and a (C6 to C14) aryl (C1 to Cq) alkyl group; and R 3 is preferably a C1 to - 5 C 12 alkyl group, a C 8 to C 14 aryl group, a (C 1 to C 8 ) alkyl (C6 to C 14 ) aryl group and a (C6 to C1) aryl (C1 to C8) alkyl group. 5 The organosiloxanes that are preferred in the compositions of the present invention may be represented by the formula: Ril R4 N- R3-Si R2 O R5 IzR6 R9 - Si 10 in which:

R

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

R'

4 represents a halogen or a group OR,,; R7 represents a halogen or a group OR 1 or R" 1 ; 15 R 9 represents a halogen or a group OR, R" 2 or R 3

NR

1

R

2 ;

R"

1 , R" 2 , Re, RIO and R 11 represent a saturated or unsaturated, linear or branched hydrocarbon-based group optionally bearing additional chemical groups such as basic solubilizing groups; 20 R 1 , Rio and R, also possibly denoting hydrogen. Preferably, R" 1 , R" 2 , R. or RIO and R 11 represent a C 1 to C12 alkyl group, a C6 to C14 aryl group, a (C1 to C 8 ) alkyl (C. to C, 4 ) aryl group and a (C 6 to C,4) aryl (Cl to C8) alkyl 25 group. At least one of the groups R,, R 7 and R, denotes a halogen or a group OR"', ORio or OR. 30 Preferably, the halogen is chlorine.

- 6 One class of organosilicon compounds that is particularly preferred consists of compounds of formula: ,OR H2N-( CH2n - Si- OR 'NOR 5 in which the radicals R, which may be identical or different, are chosen from C 1 -C, alkyl radicals such as methyl, ethyl, propyl and butyl and n is an integer from 1 to 6 and preferably from 2 to 4. 10 One organosilicon compound which is particularly recommended is y-aminopropyltriethoxysilane. The content of organosilicon compounds in the compounds 15 of the invention relative to the total weight of the composition is at least 0.02% by weight and preferably at least 0.5% by weight, and up to 20% by weight. The content of organosilicon compounds according to the 20 invention is determined by the usual analytical methods such as silicon-29 and proton NMR spectroscopy and chromatography. As mentioned above, the detergent compositions according 25 to the invention contain at least one detergent surfactant chosen from anionic, amphoteric and nonionic surfactants with detergent properties. Among the anionic surfactants which may be mentioned are 30 the alkali metal salts, ammonium salts, amine salts, amino alcohol salts and magnesium salts of the following compounds: alkyl sulfates, alkyl ether sulfates, alkyl amidoether sulfates, alkylarylpolyether sulfates, mono glyceride sulfates; alkyl sulfonates, alkylamide sulf 35 onates, alkylaryl sulfonates, olefin sulfonates, paraffin -7 a sulfonates; alkyl sulfosuccinaes, alkyl ether sulfosuccinates, alkylamide sulfosuccinates; alkyl sulfosuccinamates; alkyl sulfoacetates; alkyl phosphates, alkyl ether phosphates; acyl sarcosinates, acyl isethio 5 nates and N-acyl taurates. The alkyl or acyl radical in these various compounds generally consists of a carbon-based chain containing from 12 to 20 carbon atoms. 10 Among the anionic surfactants which may also be mentioned are fatty acid salts such as oleic, ricinoleic, palmitic and stearic acid salts; coconut oil acid or hydrogenated coconut oil acid; acyl lactylates, in which the acyl 15 radical contains from 8 to 20 carbon atoms. Surfactants considered as weakly anionic can also be used, such as polyoxyalkylenated carboxylic alkyl or alkylaryl ether acids or salts thereof, polyoxyalkyl 20 enated carboxylic alkylamido ether acids or salts there of, and alkyl-D-galactosiduronic acids or salts thereof. The nonionic surfactants are chosen more particularly from polyethoxylated, polypropoxylated or poly 25 glycerolated fatty acids or alkylphenols or alcohols, with a fatty chain containing 8 to 18 carbon atoms, the number of ethylene oxide or propylene oxide groups being between 2 and 50 and the number of glycerol groups being between 2 and 30. 30 Mention may also be made of copolymers of ethylene oxide and propylene oxide; condensates of ethylene oxide and of propylene oxide with fatty alcohols; polyethoxylated fatty amides preferably containing 2 to 30 mol of 35 ethylene oxide; polyglycerolated fatty amides preferably comprising 1 to 5 and in particular 1.5 to 4 glycerol - 8 groups; polyethoxylated fatty amines preferably containing 2 to 30 mol of ethylene oxide; oxyethylenated fatty acid esters of sorbitan with 2 to 30 mol of ethylene oxide; fatty acid esters of sucrose, fatty acid 5 esters of polyethylene glycol, alkylpolyglycosides, carbamate or amide derivatives of N-alkylglucamines, aldobionamides, amine oxides such as alkylamine oxides or of N-acylamidopropylmorpholine. 10 The preferred amphoteric surfactants are secondary or tertiary aliphatic amine derivatives, in which the aliphatic radical is a linear or branched chain containing 8 to 22 carbon atoms and which contains at least one carboxylate, sulfonate, sulfate, phosphate or 15 phosphonate water-solubilizing anionic group; (C 8

-C

20

)

alkylbetaines, sulfobetaines, (C 2

-C

2 0 ) alkylamido (C 1

-C

6 ) alkylbetaines or (C 8

-C

2 0 ) alkylamido (C 1

-C

6 ) alkylsulfo betaines. 20 Among the amine derivatives which may be mentioned are the products sold under the name Miranol, such as those 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 25 Lauroamphodiacetate, Disodium Capryloamphodiacetate, Disodium Caproamphodiacetate, Disodium Cocoamphodipropionate, Disodium Lauroamphodipropionate, Disodium Caproamphodipropionate, Disodium Capryloamphodipropionate, Lauroamphodipropionate acid, 30 Cocoamphodipropionate acid. The surfactants are used in the compositions in accordance with the invention in proportions that are sufficient to give the composition a detergent nature, 35 generally in the proportion of at least 4% by weight and preferably between 5% and 50% by weight relative to the - 9 total weight of the composition, and in particular between 8% and 35%. The compositions according to the invention have a pH 5 generally of 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 solvent(s) chosen from 10 lower alcohols, alkylene glycols and polyolethers; the water is present in proportions of greater than 20% and preferably greater than 45%. The compositions according to the invention may also 15 contain viscosity modifiers, such as electrolytes, for instance sodium chloride, thickeners, for instance cellulose derivatives such as, for example, carboxy methylcellulose, hydroxypropylcellulose, hydroxyethyl cellulose, guar gum, hydroxypropyl guar gums, sclero 20 glucans or xanthan gum. These viscosity modifiers are used in proportions ranging up to 15% by weight relative to the total weight of the composition and preferably less than 6%. 25 The compositions in accordance with the invention can optionally also contain other agents, provided that they do not affect the stability of the compositions, such as cationic surfactants, cationic, anionic, amphoteric or 30 nonionic polymers, or quaternized or non-quarternized proteins, or silicone oils, waxes, gums or resins. The polymers, the cationic surfactants, the quaternized or non-quaternized proteins and the silicones are used in 35 the cosmetic or dermatological compositions according to the invention in proportions of between 0.05% and 10% and - 10 preferably between 0.1% and 5% relative to the total weight of the composition. The compositions according to the invention may also 5 contain various adjuvants commonly used in cosmetics, such as fragrances, preserving agents, sequestering agents, foam stabilizers, propellants, colorants, antidandruff agents, ceramides, vitamins or provitamins, hydroxy acids, acidifying or basifying agents or other 10 adjuvants depending on the use envisaged. The processes for washing and/or conditioning the hair or the skin consist in applying thereto a composition as defined above, this application being followed by 15 rinsing. The compositions in accordance with the invention may also be used as shower gels for washing the hair and the skin, in which case they are applied to wet skin and wet 20 hair and are rinsed out after application. The examples which follow are intended to illustrate the invention without, however, being limiting in nature. 25 EXAMPLES Example 1: The washing compositions in Table I below were formulated. Table I 30 A B (invention) Sodium (C 1 2

-C

14 ) alkyl ether 8 AM 8 AM sulfate oxyethylenated with [2.2 mol of ethylene oxide, sold 35 containing 70% AM - 11 Laurylbetaine as an aqueous 2 AM 2 AM solution containing 30% AM Aminopropyltriethoxysilane - 5 (APTES) 5 Aqueous 0.1N hydrochloric acid 1.5 1.5 solution at pH = 1 Water qs 100 100 Evaluation of the treating properties: 10 Locks of natural hair were treated with the two compositions, under the following conditions: 1 g of composition per 2.5 g lock Exposure time = 10 minutes 15 Rinsing with running water = passed between 2 fingers 20 times Drying = 10 minutes at 60*C. The two locks were then submitted to a panel of testers 20 who were asked the question: "which lock is the more coated and the more textured"? The 10 testers unanimously considered that the locks treated with composition B are more coated and have 25 more texture than the locks treated with composition A. Example 2: The compositions in Table II below were formulated. 30 - 12 Table II C D (invention) Sodium (C 1 2

-C

1 4 )alkyl ether 10 AM 10 AM 5 sulfate oxyethylenated with [2.2 mol of ethylene oxide, sold containing 70% AM Alkylpolyglucoside as an aqueous 5 AM 5 AM solution containing 53% AM, sold 10 under the name Plantacare@2000 UP by the company Henkel Aminopropyltriethoxysilane - 5 (APTES) Aqueous 0.lN hydrochloric acid 1.5 1.5 15 solution at pH = 1 Water qs 100 100 Evaluation of the treating properties: 20 Locks were treated as in Example 1. The two locks were then submitted to a panel of testers who were asked the question: "which lock is the more coated and the more textured"? 25 The 10 testers unanimously considered 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 5 cosmetically acceptable aqueous medium, at least 0.02% by weight, relative to the total weight of the composition, of one or more water-soluble organo silicon compounds chosen from silanes comprising one silicon atom and siloxanes comprising two or three 10 silicon atoms, this organosilicon compound also comprising at least one basic chemical function and at least two hydrolyzable or hydroxyl groups per molecule, and at least 4% by weight, relative to the total weight of the composition, of a detergent 15 surfactant chosen from anionic, amphoteric and nonionic surfactants, and mixtures thereof.

2. Composition according to Claim 1, characterized in that the water-soluble organosilicon compound 20 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 25 organosilicon compound is chosen from primary, secondary and tertiary amines.

4. Composition according to any one of Claims 1 to 3, characterized in that the hydrolyzable groups are 30 chosen from alkoxy, aryloxy and halogen groups.

5. Composition according to any one of the preceding claims, characterized in that the organosilicon compound(s) is (are) chosen from the compounds of 35 formulae: - 14 RI R 4 N - R 3 - Si-R 5 Rj R6 in which: R 4 represents a halogen or a group OR' or R' 1 ; R 5 represents a halogen or a group OR" or R'; 5 R. represents a halogen or a group OR"' or R',; and R 1 , R 2 , R 3 , R', R", R"', R' 1, R' 2 and R', represent, independently of each other, a saturated or unsaturated, linear or branched hydrocarbon-based group optionally bearing 10 additional chemical groups, R 1 , R 2 , R', R" and R"' also possibly denoting hydrogen, at least two of the groups R4, R and R being other than groups R' 1 , R'2 and R' 3 ; and RI\R R7 15 in which: R 1 , R 2 , R 3 , R. and R are defined as above; R' 4 represents a halogen or a group ORu 1 ; R 7 represents a halogen or a group ORi, or R" 1 ; R, represents a halogen or a group ORE, R" 2 or 20 R 3 NR 1 R 2 ; R" 1 , R" 2 , R, RIO and R 11 represent a saturated or unsaturated, linear or branched hydrocarbon-based group optionally bearing additional chemical groups, the groups R 11 , Ri 0 and R also possibly denoting 25 hydrogen; at least one of the groups R, R 7 and R. - 15 denotes a halogen or a group OR"', ORIO or ORs.

6. Composition according to Claim 5, characterized in that the groups R 1 , R21, R', R' 1 , R' 2 , R' 3 , R", R"', 5 R" 1 , R" 2 , Rs, R, 0 and Ru are chosen from C 1 -C 1 , alkyl, C6 to C 14 aryl, (C 1 to C.) alkyl (C. to C 14 ) aryl and (C 6 to C 14 ) aryl (C 1 to C8) alkyl radicals.

7. Composition according to any one of Claims 1 to 6, 10 characterized in that the organosilicon compound has the formula: OR H 2 N ( CH2)n - Si -OR OR in which the radicals R, which may be identical or different, are chosen from C,-C6 alkyl radicals and 15 n is an integer from 1 to 6 and preferably from 2 to 4.

8. Composition according to Claim 7, characterized in that the organosilicon compound is y 20 aminopropyltriethoxysilane.

9. Composition according to any one of the preceding claims, characterized in that the detergent surfactant is present in a proportion of from 5% to 25 50% by weight and preferably from 8% to 35% by weight relative to the total weight of the composition.

10. Composition according to any one of the preceding 30 claims, characterized in that the anionic surfactants are chosen from the alkali metal salts, magnesium salts, ammonium salts, amine salts and - 16 amino alcohol salts of the following compounds: alkyl sulfates, alkyl ether sulfates, alkyl amidoether sulfates, alkylarylpolyether sulfates, monoglyceride sulfates; alkyl sulfonates, alkylamide 5 sulfonates, alkylaryl sulfonates, olefin sulfonates, paraffin sulfonates; alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates; alkyl sulfosuccinamates; alkyl sulfoacetates; alkyl phosphates, alkyl ether phosphates; acyl sarco 10 sinates, acyl isethionates and N-acyl taurates; the alkyl or acyl radical of these various compounds consists of a carbon-based chain containing from 12 to 20 carbon atoms; fatty acid salts of oleic, ricinoleic, palmitic or stearic acid; coconut oil 15 acid or hydrogenated coconut oil acid; acyl lactylates, in which the acyl radical comprises from 8 to 20 carbon atoms; alkyl-D-galactosiduronic acids and salts thereof, polyoxyalkylenated alkyl or alkylaryl ether carboxylic acids or salts thereof, 20 polyoxyalkylenated alkylamido ether carboxylic acids or salts thereof.

11. Composition according to any one of Claims 1 to 9, characterized in that the nonionic surfactants are 25 chosen from polyethoxylated, polypropoxylated or polyglycerolated fatty acids or alkylphenols or alcohols, with a fatty chain containing 8 to 18 carbon atoms, the number of ethylene oxide or propylene oxide groups being between 2 and 50 and 30 the number of glycerol groups being between 2 and 30; copolymers of ethylene oxide and propylene oxide; condensates of ethylene oxide and of propylene oxide with fatty alcohols; polyethoxylated fatty amides; polyglycerolated fatty amides; 35 polyethoxylated fatty amines; oxyethylenated fatty acid esters of sorbitan; fatty acid esters of - 17 sucrose or of polyethylene glycol, alkylpoly glycosides; carbamate or amide derivatives of N alkylglucamide, aldobionamides and amine oxides. 5

12. Composition according to any one of Claims 1 to 9, characterized in that the amphoteric surfactants are chosen from secondary or tertiary aliphatic amine derivatives, in which the aliphatic radical is a linear or branched chain containing 8 to 18 carbon 10 atoms and which contains at least one carboxylate, sulfonate, sulfate, phosphate or phosphonate water solubilizing anionic group; (C-C 2 0 )alkylbetaines, sulfobetaines, (C 8 -C 2 0 )alkylbetaines [sic) or (C 8 -C 0 ) alkylamido (C 1 -C 6 )alkylsulfobetaines. 15

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

14. Composition according to any one of Claims 1 to 13, characterized in that the composition also contains 25 viscosity modifiers chosen from electrolytes, hydrotropes or thickeners present in proportions which may be up to 15% by weight relative to the total weight of the composition. 30

15. Composition according to any one of Claims 1 to 14, characterized in that it also contains one or more adjuvants chosen from cationic surfactants, anionic, nonionic, cationic or amphoteric polymers, optionally quaternized proteins and a silicone oil, 35 wax, gum or resin. - 18

16. Composition according to any one of Claims 1 to 15, characterized in that it contains various cosmetically acceptable adjuvants chosen from fragrances, preserving agents, sequestering agents, 5 foam synergists, foam stabilizers and acidifying or basifying agents.

17. Use, as a shampoo, of the composition as defined in any one of Claims 1 to 16. 10

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

19. Process for washing keratin materials, characterized 15 in that at least one composition as defined in any one of Claims 1 to 16 is applied to these materials and, after an exposure time, the treated materials are rinsed with water.