COMPOSITIONS COMPRISING AT LEAST ONE COMPOUND OF THE N-ACYLAMINO AMIDE FAMILY AND AT LEAST ONE ALKYL POLYGLYCOSIDE

Abstract

The invention relates to a composition, in particular a cosmetic composition, preferably in the form of an oil-in-water emulsion, comprising: at least one compound of the family of N-acylamino amides of formula (I); [Chem 10] at least one alkyl polyglycoside of formula (IV) below: R9(0)(G)x (iv) in which the radical R9 is a linear or branched C14-C24 alkyl radical, G represents a reduced sugar comprising from 5 to 6 carbon atoms; and x denotes a value ranging from 1 to 10 and preferably from 1 to 4. In particular, said composition also comprises at least one compound chosen from oxyethylenated sorbitan esters and fatty acid esters of a polyoxyalkylene glycol. Use for caring for, making up and/or cleansing keratin materials, in particular the skin.

##STR00001##

Claims

1. A composition comprising: at least one alkyl polyglycoside of formula (IV) below:
R.sub.9(O)(G).sub.x   (IV) in which the radical R.sub.9 is a linear or branched C.sub.14-C.sub.24 alkyl radical; G represents a reduced sugar comprising from 5 to 6 carbon atoms; and x denotes a value ranging from 1 to 10; and at least one compound of formula (I) below: ##STR00009## in which: the radical Y represents O or S, the radical R1 represents: (i) a hydrogen atom; (ii) a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 18 carbon atoms, optionally substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR; —O—COR; —SH; —SR; —S—COR; —NH.sub.2; -—NHR; —NRR′; —NH—COR; -Hal (halogen); —CN; —COOR; —COR; —P(O)—(OR).sub.2; —SO.sub.2—OR; with R and R′ representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated, or even perhalogenated, it being possible for said radicals R and R′ to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; (iii) a radical chosen from the radicals —OR; —NH.sub.2; —NHR; —NRR′; —NH—COR; —COOR; —COR; with R and R′ representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated, it being possible for said radicals R and R′ to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; the radical R2 represents a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based group comprising 1 to 18 carbon atoms, optionally substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR; —O—COR; —SH; —SR; —S—COR; —NH.sub.2; —NHR; —NRR′; —NH—COR; -Hal (halogen); —CN; —COOR; —COR; with R and R′ representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated, it being possible for said radicals R and R′ to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; the radical R3 represents a radical chosen from those of formula (II) or (III): (II) —A—C6H(5-y)-By (III) —C6H(5-y′)-By in which: y is an integer between 0 and 5 included, and y′ is an integer between 1 and 5 included; A is a linear or branched, saturated or unsaturated, divalent hydrocarbon-based radical comprising 1 to 18 carbon atoms, optionally substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR; —O—COR; —SH; —SR; —S—COR; —NH.sub.2; —NHR; —NRR′; —NH—COR; -Hal (halogen or perhalogen); —CN; —COOR; —COR; -—NO.sub.2; —SO.sub.2—OR; with R and R′ representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated, it being possible for said radicals R and R′ to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; B is a linear or branched, saturated or unsaturated hydrocarbon-based radical comprising 1 to 18 carbon atoms, optionally substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR; —O—COR; —SH; —SR; —S—COR; —NH.sub.2; —NHR; —NRR′; —NH—COR; -Hal (halogen or perhalogen); —CN; —COOR; —COR; —NO.sub.2; —SO.sub.2—OR; with R and R′ representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated, it being possible for said radicals R and R′ to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; the radical X represents a radical chosen from —OH, —OR4, —NH.sub.2, —NHR4, —NR4R5, —SR4, ——COOR4; —COR4; with R4 and R5 representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, optionally substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR; —O—COR; —SH; —SR; —S—COR; —NH.sub.2; —NHR; —NRR′; —NH—COR; -Hal (halogen or even perhalogen); —CN; —COOR; —COR; with R and R′ representing, independently of one another, a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; it being possible for said radicals R and R′ to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; it being possible for said radicals R4 and R5 to form, together with N, a 5 or 6-membered carbon-based ring which may also comprise at least one heteroatom chosen from O, N and/or S in the ring, and/or to be substituted with 1 to 5 groups, which may be identical or different, chosen from —OH; —OR″; —O—COR″; —SH; —SR″; —S—COR″; —NH.sub.2; —NHR″; —NH—COR″; -Hal (halogen); —CN; —COOR″; —COR″; with R″ representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; inorganic or organic acid salts thereof, optical isomers thereof, in isolated form or as a racemic mixture.

2. The composition according to claim 1 1, which is a composition in the form of an oil-in-water emulsion.

3. The composition according to claim 1, wherein said composition also comprises at least one additional emulsifying surfactant.

4. The composition according to claim 1, wherein, for said compound of formula (I): the radical Y represents oxygen; and/or the radical R1 represents hydrogen or an optionally substituted linear or branched, saturated or unsaturated hydrocarbon-based radical comprising 1 to 12 carbon atoms; and/or the substituents of R1 are chosen from —OH, —OR and/or —P(O)—-(OR).sub.2 with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; and/or the radical R2 represents an optionally substituted linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 12 carbon atoms; and/or the substituents of R2 are chosen from —OH and —OR with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; and/or the radical R3 represents a radical of formula —C.sub.6H(5-y′)-By′ for which y′=1, 2 or 3; or a radical of formula —A—C.sub.6H(5-y)-By for which y=0, 1 or 2; and/or the radical A of R3 is an optionally substituted linear or branched, saturated or unsaturated, divalent hydrocarbon-based radical comprising 1 to 12 carbon atoms; and/or the radical B of R3 is an optionally substituted linear or branched, saturated or unsaturated hydrocarbon-based radical comprising 1 to 12 carbon atoms; and/or the substituents of A and/or of B are chosen from -Hal (halogen, or perhalogen); —CN; —COOR; -—NO.sub.2; —SO.sub.2—OR; with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated; and/or the radical X represents a radical chosen from —OH or —OR4 with R4 representing an optionally substituted linear, cyclic or branched, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms; and/or the substituents of R4 of X are chosen from —OH and —OR with R representing a linear, branched or cyclic, saturated or unsaturated hydrocarbon-based radical comprising 1 to 6 carbon atoms, which is optionally halogenated or perhalogenated.

5. The composition according to claim 1, wherein, for said compound of formula (I): the radical R1 represents a methyl, ethyl, propyl or isopropyl radical, optionally substituted with an —OH for —P(O)—(OR).sub.2 group with R representing methyl, ethyl, propyl or isopropyl; and/or the radical R2 represents a methyl, ethyl, propyl, isopropyl, n-butyl, ter-butyl or isobutyl radical; and/or the radical R3 represents a group chosen from one of the formulae below: ##STR00010## in which the divalent radical A is a methylene, an ethylene, a propylene and/or the radical B is a methyl, ethyl, propyl or isopropyl radical, substituted with one or more halogens; the radical X represents a radical chosen from —OH, —OCH.sub.3, —OC.sub.2H.sub.5, —O—C.sub.3H.sub.7 or —OC.sub.4H.sub.9.

6. The composition according to claim 1, wherein, said compound of formula (I) is chosen from: [2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetic acid, ethyl[2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetate, [2-(acetylbenzylamino)-3-methylbutyrylamino]acetic acid, ethyl[2-(acetylbenzylamino)-3-methylbutyrylamino]acetate, and ethyl(2-[benzyl[(diethoxyphosphoryl)acetylamino]-3-methylbutyrylamino)acetate.

7. The composition according to claim 1, wherein the alkyl polyglycoside(s) are chosen from the compounds of formula (IV′) below:
R.sub.9′—O-G   (IV′) in which: the radical R.sub.9′ is a branched alkyl radical comprising from 14 to 24 carbon atoms and G denotes a reduced sugar comprising from 5 to 6 carbon atoms.

8. The composition according to claim 1, also comprising at least one fatty alcohol comprising from 14 to 24 carbon atoms and having the same fatty chain as that of the alkyl polyglycoside.

9. The composition according to claim 8, in which the alkyl polyglycoside is octyldodecyl xyloside and the fatty alcohol is octyldodecanol.

10. The composition according to claim 8, in which the mixture of octyldodecyl xyloside and octyldodecanol is present in a content ranging from 0.01% to 50% by weight relative to the total weight of the composition.

11. The composition according to claim 9, in which the amount of octyldodecyl xyloside ranges from 20% to 30% by weight relative to the total weight of the mixture of octyldodecyl xyloside and octyldodecanol.

12. The composition according to claim 9, in which the amount of octyldodecanol ranges from 70% to 80% by weight relative to the total weight of the mixture of octyldodecyl xyloside and octyldodecanol.

13. The composition according to claim 1, wherein said compound(s) of formula (I) is (are) present in a content ranging from 0.001% to 50% by weight relative to the total weight of the composition.

14. The composition according to claim 3, wherein the oxyethylenated sorbitan ester(s) is(are) chosen from C.sub.8-C.sub.30 fatty acid monoesters and polyesters of sorbitan, having from 1 to 50 ethylene oxide units.

15. The composition according to claim 3, wherein the fatty acid ester(s) of a polyoxyalkylene glycol is (are) chosen from polyhydroxylated fatty acid esters of polyethylene glycol, in particular in which the fatty acid comprises from 12 to 20 carbon atoms and the polyethylene glycol comprises from 4 to 5 mol of ethylene oxide.

16. The composition according to claim 15, also comprising at least one N-acylamino acid ester of formula (VII) below:
R′.sub.1(CO)N(R′.sub.2)CH(R′.sub.3)(CH.sub.2)n(CO)OR′.sub.4   (VII) in which: n is an integer equal to 0, 1 or 2, R′.sub.1 represents a linear or branched C.sub.5-C.sub.21 alkyl or alkenyl radical, R′.sub.2 represents a hydrogen atom or a C.sub.1 to C.sub.3 alkyl group, R′.sub.3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C.sub.3 or C.sub.4 alkyl radical, R′.sub.4 represents a linear or branched C.sub.1 to C.sub.10 alkyl or C.sub.2 to C.sub.10 alkenyl radical, or a sterol residue.

17. The composition according to claim 16, in which the N-acylamino acid ester of formula (VII) is isopropyl N-lauroylsarcosinate of formula: ##STR00011##

18. A cosmetic process for treating keratin materials, comprising the application to the keratin materials of a composition as claimed in claim 1.

19. A cosmetic process for treating ageing, for improving the quality of the barrier function of and/or for regenerating keratin materials comprising the application to said keratin materials of a composition as defined according to claim 1.

20. A cosmetic process for caring for, protecting and/or making up of bodily and/or facial skin.

Description

Example 1

[0326] The following compositions in accordance with the invention were prepared:

TABLE-US-00001 TABLE 1 Starting Commercial Phase material Reference Composition 3 Composition 4 Composition 1 Composition 2 A WATER 72.3 66.894 73.19 67.47 SODIUM CAUSTIC 0.206 0.11 0.03 HYDROXIDE LYE(GUJARAT ALKALIES AND CHEMICALS) SODIUM CRISTALHYAL LO 0.1 0.5 HYALURONATE (SOLIANCE (GIVAUDAN)) ACETYL MEXORYL SAR 2 2 1 1 TRIFLUOROMETHYLPHENYL (CHIMEX) VALYLGLYCINE ([2-[acetyl- (3-trifluoro- methylphenyl)amino]- 3-methylbutyrylamino]- acetic acid) PHENOXYETHANOL SEPICIDE LD 0.5 0.5 0.5 0.5 (SEPPIC) DIPROPYLENE DIPROPYLENEGLYCOL 2 2 GLYCOL CARE (BASF) BUTYLENE 1,3 BUTYLENE 2 2 GLYCOL GLYCOL (DAICEL) DENAT. SURFIN 2 2 ALCOHOL DEHYDRATED ABSOLUTE ALCOHOL 0.1% TBA + 10 MG/L BITREX (TEREOS) GLYCERIN ECOCEROL 7 7 7 7 (ECOGREEN OLEOCHEMICALS) PENTYLENE 616751 2 2 GLYCOL HYDROLITE-5 ® (SYMRISE) CAPRYL HYDROLITE CG ® 0.7 0.3 0.7 0.3 GLYCOL (SYMRISE) B POLYSORBATE TWEEN 20- 0.2 0.2 20 LQ-(AP) ® from the company Croda PEG-30 CITHROL 0.5 0.5 DIPOLYHYDROXYSTEARATE DPHS-SO- (MV) ® by the company Croda OCTYLDODECANOL FLUIDANOV 2 2 2 2 (and) OCTYLDODECYL 20 X ® XYLOSIDE (SEPPIC) ISOPROPYL LAUROYL ELDEW SL-205 4.5 4.5 SARCOSINATE (AJINOMOTO) C CYCLOHEXASILOXANE XIAMETER PMX-0246 6 6 CYCLOHEXASILOXANE(DOW CORNING (DOW CHEMICAL) DIMETHICONE XIAMETER PMX-200 2 2 SILICONE FLUID 5 CST (DOW CORNING (DOW CHEMICAL)) DIMETHICONE DOW CORNING EL- 2 2 CROSSPOLYMER 9240 SILICONE ELASTOMER BLEND (DOW CORNING (DOW CHEMICAL)) DIMETHICONE (and) X-25-7034H (SHIN 5 5 DIMETHICONE/VINYL ETSU) DIMETHICONE CROSSPOLYMER D XANTHAN GUM RHODICARE 0.3 0.3 XC (PMC OUVRIE) SODIUM SIMULGEL 5 5 ACRYLATE/SODIUM EG (SEPPIC) ACRYLOYLDIMETHYL TAURATE COPOLYMER (and) ISOHEXADECANE (and) POLYSORBATE 80 POLYACRYLATE SEPIMAX ZEN 1 1 CROSSPOLYMER-6 (SEPPIC) E TOCOPHERYL VITAMIN 0.2 ACETATE E ACETATE CARE (BASF) BORON NITRIDE 2 2

[0327] Method for preparing compositions 1, 2, 3 and 4 according to the invention:

[0328] Mix phase A and heat to 50° C. to dissolve the active agent.

[0329] Add phase B.

[0330] Mix and heat the fatty phase C to 30° C.

[0331] Incorporate phase C into phase A+B in one step. Mix slowly with a spatula.

[0332] Observation of diffusion, mix until an emulsion is obtained.

[0333] Mix for a few minutes using a deflocculating device.

[0334] Add phase D, then phase E after emulsification.

[0335] The compositions according to the invention 1, 2, 3 and 4 can be applied to the skin for cosmetic treatment of the skin, in particular in order to treat the signs of age.

[0336] These compositions may be applied regularly to facial skin in order to attenuate the signs of skin ageing.

Example 2: Evaluation of the Stability

[0337] Compositions 1, 2, 3 and 4 of Example 1, in accordance with the invention, were tested for stability according to the following methodology.

[0338] Samples of the three formulations were placed in storage for 2 months at 4° C., ambient temperature, 40° C. and/or 45° C. They were then controlled on the basis of the following criteria: macroscopic appearance, microscopic appearance (light microscope magnification ×10, normal and polarized light), pH, viscosity.

[0339] It was noted that the three compositions 1, 2, 3 and 4 in accordance with the invention are stable at ambient temperature and at 2 months at 45° C., and exhibit no recrystallization of the compound of formula (I); this compound, [2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetic acid, is therefore very well dissolved in these particular combinations.

Example 3: Evaluation of the Skin Bioavailability

[0340] Test for diffusion of the compound of formula (I) through the Strat-M© membrane

[0341] This method makes it possible to measure the amount of active agent that diffuses through a membrane which mimics the behaviour of the skin (Strat-M© from Millipore). Each formula is evaluated on 3 to 9 independent Franz cells.

[0342] Protocol:

[0343] The membrane is placed on a Franz cell, after the receptor compartment has been filled with a phosphate buffer (PBS). The formula containing the active agent is applied to the donor compartment, at a finite dose of 25 mg/cm.sup.2. The receptor compartment is stirred (600 rpm) for 5 h.

[0344] The receptor liquid is sampled after 5 h and the amount of active agent that has diffused is measured (UPLC/UV).

[0345] The table below presents the results obtained.

TABLE-US-00002 TABLE 2 Bioavailability on Stat-M Composition 1 Composition 2 mean μg/cm2 87.56 169.67 standard deviation 35.88 4.04

[0346] Surprisingly, a composition according to the invention comprising at least one alkyl polyglycoside compound of formula (IV), such as octyldodecyl xyloside, combined with an oxyethylenated sorbitan ester, such as polysorbate 20, or a fatty acid ester of a polyoxyalkylene glycol, such as PEG-30 dipolyhydroxystearate, allows very good membrane permeation of a compound of formula (I), such as [2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetic acid.

Test for Bioavailability of a Compound of Formula (I) on Human Skin Ex Vivo

[0347] This evaluation is carried out by characterization of the skin absorption of a compound of formula (I) such as [2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetic acid.

[0348] This skin absorption was evaluated according to OECD Guidelines (OECD guideline for the testing of chemicals: guideline 428, skin absorption: in vitro method (13 Apr. 2004)). The studies are performed on frozen human skin obtained from abdominal plastic surgery following application of a finite dose of formulation (e.g. 5 mg/cm.sup.2) for 16 hours. The quantitative analysis is carried by means of a validated LC/MS/MS method, the skin bioavailability being measured according to the definition provided by the SCCS.

[0349] A non-parametric statistical analysis based on R-estimators is used.

[0350] Table 3 below gives the results obtained.

TABLE-US-00003 TABLE 3 Skin bioavailability μg/cm.sup.2 (±SD) % Dose applied (±SD) Composition 3 2.81 ± 1.90 3.00 ± 1.88 according to the invention Composition 4 7.16 ± 5.32 7.87 ± 5.66 according to the invention

[0351] Surprisingly, a composition according to the invention comprising at least one alkyl polyglycoside compound of formula (IV), such as octyldodecyl xyloside, combined with an oxyethylenated sorbitan ester, such as polysorbate 20, or a fatty acid ester of a polyoxyalkylene glycol, such as PEG-30 dipolyhydroxystearate, allows good skin bioavailability of a compound of formula (I), such as [2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetic acid.

[0352] Taking these results into account along with those presented above in regard to stability shows that the compositions in accordance with the invention are able to jointly have excellent stability and a probably greater efficacy of [2-[acetyl-(3-trifluoromethylphenyl)amino]-3-methylbutyrylamino]acetic acid given the increase in skin bioavailability observed.