COMPOSITION COMPRISING AT LEAST ONE ALKOXYSILANE OF FORMULA (I), AT LEAST ONE ALKOXYSILANE OF FORMULA (II), AT LEAST ONE NONAMINO SILICONE, AND OPTIONALLY PIGMENTS AND/OR DIRECT DYES

Abstract

The present invention relates to a composition (F) for treating keratin fibers, notably human keratin fibers such as the hair, comprising at least one alkoxysilane of formula (I), at least one alkoxysilane of formula (II), at least one nonamino silicone of formula (III), optionally at least one coloring agent chosen from pigments, direct dyes and mixtures thereof, and optionally water.

Claims

1-22. (canceled)

23. A composition (F) for treating keratin fibers comprising: a) at least one alkoxysilane chosen from compounds of formula (I) below, oligomers thereof, or mixtures thereof: ##STR00028## in which: R′a, R′b, R′c, and R’d are independently chosen from alkyl groups containing from 1 to 10 carbon atoms; b) at least one alkoxysilane chosen from compounds of formula (II) below, oligomers thereof, or mixtures thereof: ##STR00029## in which: R.sub.0 is chosen from alkyl groups containing from 4 to 24 carbon atoms, optionally interrupted with a dialkylammonium divalent radical R.sub.aR.sub.bN+An.sup.-, with: R.sub.a and R.sub.b independently chosen from alkyl groups containing from 1 to 10 carbon atoms, and An.sup.- represents a cosmetically acceptable anion chosen from fluoride, chloride, bromide, or iodide; R′ is independently chosen from a hydrogen atom or alkyl groups containing from 1 to 20 carbon atoms; and p denotes an integer ranging from 0 to 1; c) at least one non-amino silicone chosen from compounds of formula (III) below: ##STR00030## in which: R1 is independently chosen from hydroxyl groups, alkoxy groups containing from 1 to 2 carbon atoms, or alkyl groups containing from 1 to 2 carbon atoms; R2 is independently chosen from alkyl groups containing from 1 to 20 carbon atoms; R3 is chosen from a hydroxyl group, an alkyl group containing from 1 to 10 carbon atoms, said alkyl group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), a cycloalkyl group containing from 3 to 20 carbon atoms, said cycloalkyl optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), an alkoxy group containing from 1 to 2 carbon atoms, said alkoxy group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), an aryl group containing from 6 to 12 carbon atoms, said aryl group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), or a radical —(O)p′—Si(R.sub.1)m′(R.sub.2)n′; A is independently chosen from saturated divalent hydrocarbon-based radicals containing from 1 to 2 carbon atoms, X is chosen from a hydrogen atom or a saturated divalent hydrocarbon-based radical containing from 1 to 2 carbon atoms; m independently denotes an integer ranging from 1 to 3; n independently denotes an integer ranging from 0 to 2; m′ independently denotes an integer ranging from 1 to 3; n′ independently denotes an integer ranging from 0 to 2; p is an integer equal to 0, 1, 2, or 3; p′ is an integer equal to 0 or 1; k is an integer equal to 0, 1, 2, or 3; q is an integer equal to 0 or 1; j independently denotes an integer equal to 0 or 1; t is an integer equal to 0 or 1; y is an integer ranging from 0 to 10; z is an integer ranging from 0 to 500; m+n = 3; m′+n′ = 3; x+z ranges from 0 to 500; and x+y+z ≥ 4; with the proviso that: if X represents a hydrogen atom, then t = 0 and p = 1, and if p = 0, then t = 1 and q = 1, and that at least one of the radicals R.sub.1 or R.sub.3 denotes a hydroxyl radical or an alkoxy radical containing from 1 to 2 carbon atoms; and d) optionally at least one coloring agent chosen from pigments, direct dyes, or mixtures thereof.

24. The composition according to claim 23, wherein in formula (I), R′a, R′b, R′c, and R’d are identical and denote an ethyl radical.

25. The composition according to claim 23, comprising at least one alkoxysilane of formula (I) chosen from tetraethoxysilane (TEOS), tetrapropoxysilane, tetrabutoxysilane, tetrapentoxysilane, tetrahexyloxysilane, or mixtures thereof.

26. The composition according to claim 23, comprising a total amount of alkoxysilanes of formula (I) and oligomers thereof ranging from 0.1% to 30% by weight, relative to the total weight of composition (F).

27. The composition according to claim 23, wherein in formula (II): R′ are identical and are chosen from alkyl groups containing from 1 to 4 carbon atoms, and p is equal to 1.

28. The composition according to claim 27, wherein in formula (II), R.sub.0 is chosen from an alkyl group containing from 6 to 18 carbon atoms.

29. The composition according to claim 23, comprising a total amount of alkoxysilanes of formula (II) and oligomers thereof ranging from 0.1% to 30% by weight, relative to the total weight of composition (F).

30. The composition according to claim 23, wherein in formula (III): R2 is independently chosen from alkyl groups containing from 1 to 4 carbon atoms; R3 is chosen from a hydroxyl group or an alkyl group containing from 1 to 10 carbon atoms; j is equal to 0; and k is equal to 0.

31. The composition according to claim 30, wherein in formula (III): R2 is independently chosen from alkyl groups containing from 1 to 2 carbon atoms; m denotes an integer ranging from 1 to 3; n denotes an integer ranging from 0 to 2; j is equal to 0; - y is equal to 0; m+n = 3; and x+z ≥ 4; wherein at least one of the radicals R1 denotes a hydroxyl radical or an alkoxy radical containing from 1 to 2 carbon atoms.

32. The composition according to claim 30, wherein the at least one non-amino silicone is chosen from compounds of formula (IIIa) below: ##STR00031## in which: R.sub.1 is independently chosen from a hydroxyl group, alkyl groups containing from 1 to 10 carbon atoms, alkoxy groups containing from 1 to 2 carbon atoms, or a group —(CH.sub.2).sub.s—Si(R.sub.4).sub.3 in which s denotes an integer ranging from 1 to 4 and R.sub.4 is independently chosen from alkoxy radicals containing from 1 to 2 carbon atoms; R′.sub.2 and R″.sub.2 are independently chosen from alkyl groups containing from 1 to 10 carbon atoms; a denotes an integer ranging from 0 to 10; b denotes an integer ranging from 0 to 500; and a+b ≥ 4.

33. The composition according to claim 32, wherein in formula (IIIa): R.sub.1 is independently chosen from alkyl groups containing from 1 to 4 carbon atoms; R′.sub.2 and R″.sub.2 are independently chosen from a hydroxyl group or alkyl groups containing from 1 to 4 carbon atoms; a denotes an integer ranging from 0 to 5; and b denotes an integer ranging from 0 to 10.

34. The composition according to claim 23, wherein the at least one non-amino silicone is chosen from compounds of formula (lllc) below: ##STR00032## in which: R.sub.1 is independently chosen from alkyl groups containing from 1 to 10 carbon atoms, alkoxy groups containing from 1 to 2 carbon atoms, or a group —O—(X).sub.p—Si(OR.sub.2).sub.3with X representing a saturated divalent hydrocarbon-based radical containing from 1 to 2 carbon atoms, and p denoting an integer ranging from 0 to 3; R.sub.2 is independently chosen from alkyl groups containing from 1 to 10 carbon atoms; R′.sub.2 and R″.sub.2 are independently chosen from alkyl groups containing from 1 to 10 carbon atoms or alkoxy groups containing from 1 to 10 carbon atoms; i denotes an integer ranging from 0 to 10; n denotes an integer ranging from 0 to 500; and n+i ranges from 0 to 510.

35. The composition according to claim 34, wherein in formula (lllc): R.sub.1 and R.sub.2 are independently chosen from alkyl groups containing from 1 to 4 carbon atoms; R′.sub.2 and R″.sub.2 are independently chosen from alkoxy groups containing from 1 to 4 carbon atoms; and - n+i≥ 4.

36. The composition according to claim 23, comprising a total amount of non-amino silicones of formula (III) ranging from 0.1% to 25% by weight, relative to the total weight of composition (F).

37. The composition according to claim 23, wherein composition (F) comprises one or more organic solvent(s) chosen from C.sub.1-C.sub.4 lower alkanols.

38. A method for treating keratin fibers, comprising applying an effective amount of a composition (F) according to claim 23 to the keratin fibers.

39. A kit for treating keratin fibers comprising at least two compartments, wherein: a first compartment (E1) comprises a composition (A) comprising: a) at least one alkoxysilane chosen from compounds of formula (I) below, oligomers thereof, or mixtures thereof: ##STR00033## in which: R′a, R′b, R′c, and R’d are independently chosen from alkyl groups containing from 1 to 10 carbon atoms; and b) at least one alkoxysilane chosen from compounds of formula (II) below, oligomers thereof, or mixtures thereof: ##STR00034## in which: R.sub.0 is chosen from alkyl groups containing from 4 to 24 carbon atoms, optionally interrupted with a dialkylammonium divalent radical R.sub.aR.sub.bN+An.sup.-, with: R.sub.a and R.sub.b independently chosen from alkyl groups containing from 1 to 10 carbon atoms, and An.sup.- represents a cosmetically acceptable anion chosen from fluoride, chloride, bromide, or iodide; R′ is independently chosen form a hydrogen atom or alkyl groups containing from 1 to 20 carbon atoms; and p denotes an integer ranging from 0 to 1; and - a second compartment (E2) comprises a composition (B) comprising: c) at least one non-amino silicone chosen from compounds of formula (III) below: ##STR00035## in which: R1 is independently chosen from hydroxyl groups, alkoxy groups containing from 1 to 2 carbon atoms, or alkyl groups containing from 1 to 2 carbon atoms; R2 is independently chosen from alkyl groups containing from 1 to 20 carbon atoms; R3 is chosen from a hydroxyl group, an alkyl group containing from 1 to 10 carbon atoms, said alkyl group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), a cycloalkyl group containing from 3 to 20 carbon atoms, said cycloalkyl optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), an alkoxy group containing from 1 to 2 carbon atoms, said alkoxy group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), an aryl group containing from 6 to 12 carbon atoms, said aryl group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), or a radical —(O).sub.p’—Si(R.sub.1).sub.m’(R.sub.2).sub.n’; A is independently chosen from saturated divalent hydrocarbon-based radicals containing from 1 to 2 carbon atoms, X is chosen from a hydrogen atom or a saturated divalent hydrocarbon-based radical containing from 1 to 2 carbon atoms; m independently denotes an integer ranging from 1 to 3; n independently denotes an integer ranging from 0 to 2; m′ independently denotes an integer ranging from 1 to 3; n′ independently denotes an integer ranging from 0 to 2; p is an integer equal to 0, 1, 2, or 3; p′ is an integer equal to 0 or 1; k is an integer equal to 0, 1, 2, or 3; q is an integer equal to 0 or 1; j independently denotes an integer equal to 0 or 1; t is an integer equal to 0 or 1; y is an integer ranging from 0 to 10; z is an integer ranging from 0 to 500; m+n = 3; m′+n′ = 3; x+z ranges from 0 to 500; and x+y+z ≥ 4; with the proviso that: if X represents a hydrogen atom, then t = 0 and p = 1, and if p = 0, then t = 1 and q = 1, and that at least one of the radicals R.sub.1 or R.sub.3 denotes a hydroxyl radical or an alkoxy radical containing from 1 to 2 carbon atoms; wherein composition (A) and/or composition (B) optionally further comprise at least one coloring agent chosen from pigments, direct dyes, or mixtures thereof.

40. A process for treating keratin fibers which comprises mixing, at or about the time of use, compositions (A) and (B) to form a composition (F), and applying the composition (F) to the keratin fibers, with: composition (A) comprising: a) at least one alkoxysilane chosen from compounds of formula (l) below, oligomers thereof, or mixtures thereof: ##STR00036## in which: R′a, R′b, R′c, and R’d are independently chosen from alkyl groups containing from 1 to 10 carbon atoms; and b) at least one alkoxysilane chosen from compounds of formula (II) below, oligomers thereof, or mixtures thereof: ##STR00037## in which: R.sub.0 is chosen from alkyl groups containing from 4 to 24 carbon atoms, optionally interrupted with a dialkylammonium divalent radical R.sub.aR.sub.bN+An.sup.-, with: R.sub.a and R.sub.b independently chosen from alkyl groups containing from 1 to 10 carbon atoms, and An.sup.- represents a cosmetically acceptable anion chosen from fluoride, chloride, bromide, or iodide; R′ is independently chosen from a hydrogen atom or alkyl groups containing from 1 to 20 carbon atoms; and p denotes an integer ranging from 0 to 1; and composition (B) comprising: c) at least one non-amino silicone chosen from compounds of formula (III) below: ##STR00038## in which: R1 is independently chosen from hydroxyl groups, alkoxy groups containing from 1 to 2 carbon atoms, or alkyl groups containing from 1 to 2 carbon atoms; R2 is independently chosen from alkyl groups containing from 1 to 20 carbon atoms; R3 is chosen from a hydroxyl group, an alkyl group containing from 1 to 10 carbon atoms, said alkyl group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), a cycloalkyl group containing from 3 to 20 carbon atoms, said cycloalkyl optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), an alkoxy group containing from 1 to 2 carbon atoms, said alkoxy group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), an aryl group containing from 6 to 12 carbon atoms, said aryl group optionally substituted with at least one group chosen from a hydroxyl group (OH) or a thiol group (SH), or a radical —(O).sub.p′—Si(R.sub.1).sub.m′(R.sub.2).sub.n′; A is independently chosen from saturated divalent hydrocarbon-based radicals containing from 1 to 2 carbon atoms, X is chosen from a hydrogen atom or a saturated divalent hydrocarbon-based radical containing from 1 to 2 carbon atoms; m independently denotes an integer ranging from 1 to 3; n independently denotes an integer ranging from 0 to 2; m′ independently denotes an integer ranging from 1 to 3; n′ independently denotes an integer ranging from 0 to 2; p is an integer equal to 0, 1, 2, or 3; p′ is an integer equal to 0 or 1; k is an integer equal to 0, 1, 2, or 3; q is an integer equal to 0 or 1; j independently denotes an integer equal to 0 or 1; t is an integer equal to 0 or 1; y is an integer ranging from 0 to 10; z is an integer ranging from 0 to 500; m+n = 3; m′+n′ = 3; x+z ranges from 0 to 500; and x+y+z ≥ 4; with the proviso that: if X represents a hydrogen atom, then t = 0 and p = 1, and if p = 0, then t = 1 and q = 1, and that at least one of the radicals R.sub.1 or R.sub.3 denotes a hydroxyl radical or an alkoxy radical containing from 1 to 2 carbon atoms; wherein composition (A) and/or composition (B) optionally further comprise at least one coloring agent chosen from pigments, direct dyes, or mixtures thereof.

41. The process according to claim 40, comprising a step of treating the keratin fibers by applying to said keratin fibers a cosmetic composition (G) comprising at least one alkoxysilane chosen from the compounds of formula (XVIII) below, oligomers thereof, or mixtures thereof: ##STR00039## in which: Ra and Rb are independently chosen from a hydrogen atom, alkyl groups containing from 1 to 20 carbon atoms, cycloalkyl groups containing from 3 to 20 carbon atoms; aryl groups containing from 6 to 12 carbon atoms, or aminoalkyl groups containing from 1 to 20 carbon atoms; Rc represents a hydrogen atom, an alkyl group containing from 1 to 20 carbon atoms, or an alkoxy group containing from 1 to 10 carbon atoms Rd and Re are independently chosen from alkyl groups containing from 1 to 10 carbon atoms; and k denotes an integer ranging from 0 to 5; wherein composition (G) is applied to the keratin fibers before the application of composition (F).

42. The process according to claim 41, wherein: Ra and Rb, which are identical, represent a hydrogen atom; Rc represents an alkyl group containing from 1 to 10 carbon atoms or an alkoxy group containing from 1 to 4 carbon atoms; and k denotes an integer ranging from 1 to 3.

43. The process according to claim 41, wherein the at least one alkoxysilane of formula (XVIII) is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminopropylmethyldiethoxysilane (APMDES), N-cyclohexylaminomethyltriethoxysilane, or mixtures thereof.

44. The process according to claim 41, wherein a washing, rinsing, drying, and/or draining step is performed after applying composition (G) to the keratin fibers and before applying composition (F) to the keratin fibers.

Description

EXAMPLES

[0491] In the examples, the temperature is given in degrees Celsius and corresponds to room temperature (20-25° C.), unless otherwise indicated, and the pressure is atmospheric pressure, unless otherwise indicated.

Example 1: Measurement of the Contact Angle

[0492] In order to check the presence of a deposit at the surface of the hair, a contact angle measurement was performed on N90W (natural, 90% white) hair treated with a composition according to the invention, and compared with untreated N90W (natural, 90% white) hair.

Protocol for Measuring the Contact Angle

[0493] Hair strands mounted on supports are placed in contact with the surface of a liquid. The wetting force generated by the contact between the hair and the liquid is measured. This force varies according to the affinity of the hair for the liquid. Measurement of this force makes it possible to assess the surface state of the hair strands.

[0494] The hair strands are mounted on the support with the root upward and the end downward. Penetration is thus performed against the direction of lie of the scales.

[0495] The measuring machine used for the measurement is a Krüss K100SF tensiometer. The container containing the wetting liquid (water) is moved to come into contact with the solid sample (the hair).

[0496] The surface tension of the wetting liquid is measured with a platinum knife.

[0497] By using the equation for the knife method, the contact angle θ may be determined on establishing the value for the surface tension of ultrapure water, the wetting perimeter L and the measured force F, according to the following formula:

[00001]$\cos \theta =\frac{F}{L\cdot \sigma }$

[0498] In general, a contact angle of less than 90 ° indicates that the wettability of the surface is very favorable: the liquid then spreads over a large area of solid. Conversely, a contact angle of greater than 90 ° generally indicates that the wettability of the surface is unfavorable: the liquid will then minimize the contact with the surface and form a compact drop of liquid.

[0499] For water, a wettable surface is said to be hydrophilic, whereas a non-wettable surface is said to be hydrophobic.

[0500] Measurement of the contact angle of the untreated hair was performed on nine different hair strands and a mean was calculated.

[0501] Measurement of the contact angle of the treated hair using the composition according to the invention was performed on ten different hair strands and a mean was calculated.

[0502] The treated hair strands were treated with the composition according to the invention according to the protocol described below.

Hair Treatment Protocol

[0503] Composition P is prepared according to the following process: pure TEOS (reference 333859 sold by the company Sigma-Aldrich) and n-octyltriethoxysilane (reference 440213 sold by the company Sigma-Aldrich) are mixed with a solution of ethanol at pH = 3-4 and water, and said mixture is placed on a VWR brand magnetic stirrer (rotation speed 500 rpm) for 6 hours at a temperature of 50° C.

[0504] Composition Q is prepared according to the following process: the polydimethylsiloxane (PDMS) compound is diluted in an ethanol solution in which the pigment, present as tracer, is dispersed.

[0505] Compositions P and Q are vortex-mixed and the mixture of compositions P and Q, referred to as composition R, is applied to the locks of N90W (natural, 90% white) hair with a bath ratio of 0.75 g of composition per gram of hair.

[0506] The locks of hair are left for 5 minutes at room temperature before being dried with a hairdryer. After leaving to stand for one hour at room temperature, the locks of hair are placed in an oven at a temperature of 120° C. for 3 hours.

[0507] The various compounds are present in the amounts below (expressed in g/100 g).

TABLE-US-00001 Chemical name Composition R Tetraethoxysilane (TEOS, reference 333859 sold by the company Sigma-Aldrich ) 14 N-Octyltriethoxysilane (reference 440213 sold by the company Sigma-Aldrich ) 33.5 Polydimethylsiloxanes (PDMS) bearing hydroxyl end functions (reference DMS-S31 sold by the company Gelest) 12 Pigment (SunPURO™ Red Iron Oxide (C33-8001)) 2 Water 5.7 Ethanol qs

Result

[0508] Table 2 corresponds to the mean and standard deviation values for the entry contact angle measurements as a function of the depth for untreated N90W hair.

TABLE-US-00002 Depth (in mm) Contact angle Mean (in °) Contact angle Standard deviation 0 92.67 8.59 0.05 94.67 9.71 0.1 94.94 6.84 0.15 95.26 6.50 0.2 94.18 6.20 0.25 93.51 6.64 0.3 92.85 6.84 0.35 94.42 7.01 0.4 95.20 7.32 0.45 94.73 7.39 0.5 94.35 6.75 0.55 94.50 7.18 0.6 94.17 7.03 0.65 94.49 6.65 0.7 95.62 6.87 0.75 95.00 8.83 0.8 94.56 7.71 0.85 95.03 7.18 0.9 95.08 7.55 0.95 95.17 7.70 1 95.53 7.51 1.05 95.65 7.65 1.10 96.88 7.03 1.15 96.51 6.62 1.2 96.85 5.78 1.25 97.07 7.12 1.3 97.02 7.11 1.35 96.22 7.62 1.4 96.50 7.44 1.45 95.88 8.73 1.5 95.92 7.35 1.55 95.11 9.45 1.6 95.06 9.70 1.65 96.04 7.93 1.7 94.88 8.94 1.75 95.99 8.86 1.8 96.62 9.00 1.85 97.18 7.82 1.9 93.66 7.83

[0509] Table 3 corresponds to the mean and standard deviation values for the entry contact angle measurements as a function of the depth for N90W hair treated with composition R according to the invention.

TABLE-US-00003 Depth (in mm) Contact angle Mean (in °) Contact angle Standard deviation 0.02 103.05 2.11 0.05 111.08 4.14 0.1 118.60 9.50 0.15 113.83 7.25 0.2 116.73 8.82 0.25 115.14 6.73 0.3 114.27 7.97 0.36 115.33 8.54 0.4 11.73 6.25 0.46 116.31 7.42 0.47 114.43 7.41 0.48 113.76 5.90 0.49 114.06 6.63 0.51 115.15 6.37 0.55 114.53 5.80 0.59 113.96 6.78 0.65 113.88 7.28 0.7 113.50 7.46 0.76 113.56 6.35 0.8 113.16 4.91 0.85 113.15 6.04 0.9 114.28 7.11 0.95 113.36 9.02 1 113.21 6.92 1.05 112.26 9.84 1.1 114.05 7.71 1.16 112.77 7.43 1.2 113.77 6.92 1.25 111.83 5.18 1.3 113.95 3.86 1.36 114.84 5.22 1.4 112.74 6.00 1.45 112.58 6.26 1.5 115.81 6.51 1.55 115.32 7.47 1.6 116.07 8.15 1.65 114.77 7.28 1.71 113.11 5.12 1.75 114.04 6.42 1.8 112.77 6.12 1.85 114.53 5.95 1.88 113.47 5.81

[0510] The contact angle values greater than 90° for the locks of hair treated with composition R according to the invention confirm the presence of a hydrophobic deposit on the surface of the treated hair.

[0511] In order to evaluate the persistence of the deposit with respect to shampoo washing, the hair was subjected to a cycle of three successive shampoo washes, the locks of hair are first combed and each shampoo wash then comprises the following steps: the locks are washed using a standard shampoo (Garnier Ultra Doux), and then rinsed.

[0512] At the end of the last shampoo wash, the locks of hair are combed and dried with a hairdryer.

[0513] The contact angles were again measured and the following results were obtained.

[0514] Table 4 corresponds to the mean and standard deviation values for the entry contact angle measurements as a function of the depth for untreated N90W hair and after three shampoo washes.

TABLE-US-00004 Depth (in mm) Contact angle Mean (in °) Contact angle Standard deviation 0 83.67 5.64 0.05 88.74 5.42 0.1 89.59 6.88 0.15 88.70 6.89 0.2 88.65 6.52 0.25 88.57 7.08 0.3 88.43 7.11 0.35 88.28 6.05 0.4 88.97 6.16 0.45 88.34 6.12 0.5 89.43 5.29 0.55 90.24 5.96 0.6 89.50 5.33 0.65 89.34 6.13 0.7 89.51 5.69 0.75 89.70 6.74 0.8 88.58 6.66 0.85 88.42 6.00 0.91 88.24 6.08 0.95 88.80 6.01 1 88.96 6.33 1.05 89.10 5.15 1.06 88.77 5.38 1.10 87.98 5.50 1.15 88.68 7.61 1.2 88.25 6.75 125 88.75 7.12 1.3 88.20 6.28 1.36 88.22 6.12 1.40 88.61 5.27 1.45 88.80 4.12 1.50 88.45 5.35 1.55 88.82 5.82 1.60 90.56 6.90 1.65 86.67 10.91 1.71 87.17 10.53 1.75 87.90 9.49 1.80 88.58 9.10 1.85 87.58 8.55 1.9 87.10 8.56

[0515] Table 5 corresponds to the mean and standard deviation values for the entry contact angle measurements as a function of the depth for N90W hair treated with composition R according to the invention after three shampoo washes.

TABLE-US-00005 Depth (in mm) Contact angle Mean (in °) Contact angle Standard deviation 0.00 98.46 7.88 0.05 108.53 10.46 0.1 112.03 10.15 0.15 112.07 10.33 0.2 114.57 12.47 0.25 111.36 8.22 0.3 113.45 9.79 0.35 113.42 10.68 0.4 110.60 8.75 0.45 112.01 9.28 0.50 108.47 8.57 0.55 111.30 10.36 0.60 110.15 10.60 0.65 110.81 8.73 0.70 109.27 8.27 0.75 111.17 11.41 0.80 110.85 9.81 0.85 111.87 9.91 0.91 109.26 9.59 0.95 114.23 12.08 1.00 110.74 9.61 1.05 110.73 9.21 1.10 112.23 11.34 1.15 109.46 10.14 1.20 112.05 10.25 1.25 113.92 15.06 1.30 110.59 10.21 1.36 109.49 9.10 1.40 108.12 9.00 1.45 110.32 12.79 1.50 111.42 13.33 1.55 111.71 14.28 1.60 111.04 10.13 1.65 110.98 10.57 1.71 111.04 9.93 1.75 112.85 11.36 1.80 110.60 9.30 1.85 110.32 8.71 1.90 111.00 10.76

[0516] The contact angle values for the untreated hair after three shampoo washes are lower than those obtained for the hair treated with composition R and which has undergone three shampoo washes.

[0517] The contact angle values greater than 90 ° for the locks of hair treated with composition R and which have undergone three shampoo washes confirm the presence of a hydrophobic deposit, which is persistent with respect to shampoo washing, on the surface of the treated hair.

[0518] Thus, treatment of the hair with composition R according to the invention leads to hydrophobization of the keratin fibers which makes them less sensitive to humidity and thus to the appearance of frizziness in a humid environment, and this hydrophobization is persistent with respect to shampoo washing.

Example 2

[0519] Solution 1 (i.e. solution of tetraethoxysilane (TEOS) and of n-octyltriethoxysilane) is prepared according to the process below: [0520] pure TEOS (reference 333859 sold by the company Sigma-Aldrich) and n-octyltriethoxysilane (reference 440213 sold by the company Sigma-Aldrich) are mixed with a solution of ethanol at pH = 3-4 and water, and said mixture is placed on a VWR brand magnetic stirrer (rotation speed 500 rpm) for 6 hours at a temperature of 50° C.

[0521] Solution 2 (i.e. solution of nonamino silicone) is prepared according to the process below: [0522] the polydimethylsiloxane (PDMS) compound bearing trialkoxysilane end functions (PDMS reference Silmer TMS Di-10 sold by the company Siltech) or the polydimethylsiloxane (PDMS) compound bearing hydroxyl end functions (PDMS reference DMS-S31 sold by the company Gelest) is diluted in an ethanol solution in which the pigment (iron oxide sold by the company Sun Chemical under the name SunPuro™ Red Iron Oxide (C33-8001)) is dispersed.

[0523] Solution 1 is mixed with solution 2 and said mixture (composition A or composition B depending on the nature of the PDMS used) is applied to the keratin fibers.

[0524] The various compounds are present in the amounts below (expressed in g/100 g).

TABLE-US-00006 Chemical name Composition A Composition B Tetraethoxysilane (TEOS) 13.9 13.9 N-Octyltriethoxysilane 3.5 3.5 Polydimethylsiloxanes (PDMS) bearing trialkoxysilane end functions 12 - Polydimethylsiloxanes (PDMS) bearing hydroxyl end functions - 12 Pigment (iron oxide sold by the company Sun Chemical under the name SunPuro™ Red Iron Oxide (C33-8001)) 3 3 Water 5.7 5.7 Ethanol qs qs

Protocol

[0525] Composition A and composition B according to the invention are applied to locks of dry natural hair containing 90% white hairs, at a rate of 1 g of composition per gram of lock.

[0526] The locks of hair are then combed and dried with a hairdryer.

[0527] The locks of hair are left for two weeks at room temperature and are then placed in an oven at a temperature of 120° C. for 10 hours.

[0528] The hair is dyed uniformly and intensely.

[0529] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

Shampoo Wash Protocol

[0530] The locks are washed with a standard shampoo (Garnier Ultra Doux).

[0531] The locks of hair are then rinsed, combed and dried with a hairdryer.

[0532] The next shampoo wash is performed on the locks obtained after the application of the hairdryer.

Results

[0533] The persistence of the color of the locks was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10 °, specular component included).

[0534] In this L*a*b* system, L* represents the intensity of the color, a* indicates the green/red color axis and b* the blue/yellow color axis.

[0535] The persistence of the coloring is evaluated by the color difference ΔE between the dyed locks before shampooing, then after having undergone one and three shampoo washes according to the protocol described above. The lower the ΔE value, the more persistent the color with respect to shampoo washing.

[0536] The ΔE value is calculated according to the following equation:

[00002]$\Delta \text{E}=\sqrt{{\left(\text{L*}-{\text{L}}_{\text{o}}*\right)}^2+{\left(\text{a*}-{\text{a}}_{\text{o}}*\right)}^2+{\left(\text{b*}-{\text{b}}_{\text{o}}*\right)}^2}$

[0537] In this equation, L*a*b* represent the values measured after dyeing the hair and after performing the shampoo washes, and L.sub.0*a.sub.0*b.sub.0* represent the values measured after dyeing the hair but before shampoo washing.

TABLE-US-00007 Compositions Number of shampoo washes L* a* b* ΔE Composition A 0 30.70 34.83 24.85 0 3 33.74 31.69 21.05 5.79 Composition B 0 35.47 33.91 24.75 0 3 38.30 34.12 25.52 2.94

[0538] The locks of hair dyed with composition A according to the invention or composition B according to the invention and washed with three shampoo washes have low ΔE values.

[0539] Thus, the coloring of the keratin fibers obtained using the compositions according to the invention shows good persistence with respect to shampoo washing. Specifically, the locks of hair dyed with the compositions according to the invention and washed with three shampoo washes show good persistence of the color.

Example 3: Pretreatment With APTES

[0540] Solution 1 (i.e. solution of tetraethoxysilane (TEOS) and of n-octyltriethoxysilane) is prepared according to the process below: [0541] pure TEOS (reference 333859 sold by the company Sigma-Aldrich) and n-octyltriethoxysilane (reference 440213 sold by the company Sigma-Aldrich) are mixed with a solution of ethanol at pH = 3-4 and water, and said mixture is placed on a VWR brand magnetic stirrer (rotation speed 500 rpm) for 6 hours at a temperature of 50° C.

[0542] Solution 2 (i.e. solution of nonamino silicone) is prepared according to the process below: [0543] the polydimethylsiloxane (PDMS) compound bearing hydroxyl end functions (PDMS reference DMS-S31 sold by the company Gelest) or the polydimethylsiloxane (PDMS) compound bearing trialkoxysilane end functions (PDMS reference Silmer TMS Di-10 sold by the company Siltech) is diluted in an ethanol solution in which the pigment (iron oxide sold by the company Sun Chemical under the name SunPuro™ Red Iron Oxide (C33-8001)) is dispersed.

[0544] Solution 1 is mixed with solution 2 and said mixture (composition C or composition D depending on the nature of the nonamino silicone used) is applied to the keratin fibers.

[0545] The various compounds are present in the amounts below (expressed in g/100 g).

TABLE-US-00008 Chemical name Composition C Composition D Tetraethoxysilane (TEOS) 13.9 13.9 N-Octyltriethoxysilane 3.5 3.5 Polydimethylsiloxanes (PDMS) bearing hydroxyl end functions 12 - Polydimethylsiloxanes (PDMS) bearing trialkoxysilane end functions - 12 Pigment (iron oxide sold by the company Sun Chemical under the name SunPuro™ Red Iron Oxide (C33-8001) 3 3 Water 5.9 5.7 Ethanol qs qs

Protocol

[0546] Before applying composition C or composition D to the keratin fibers, the locks of natural hair containing 90% white hairs are pretreated with a solution 3 which is prepared according to the following process:

[0547] 3.66 g of 0.1 N HCl are added to 30 g of APTES (APTES Silsoft A- 1100 sold by the company Momentive Performance Materials) in 200 g of water. The solution obtained is stirred at room temperature for 2 hours. Once the hydrolysis is complete, the solution is transferred into a beaker containing 20 locks of natural hair containing 90% white hairs, and left under gentle stirring for 10 minutes. Once the impregnation is complete, the locks of hair are rinsed and left to dry between two sheets of absorbent paper.

[0548] Compositions C and D according to the invention are applied to dry pretreated locks of natural hair containing 90% white hairs, at a rate of 1 g of composition per gram of lock.

[0549] The locks of hair are then combed and dried with a hairdryer.

[0550] The locks of hair are left for two weeks at room temperature and are then placed in an oven at a temperature of 120° C. for 10 hours.

[0551] The hair is dyed uniformly and intensely.

[0552] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

[0553] The shampoo wash protocol is identical to that presented in Example 2.

Results

[0554] The persistence of the color of the locks was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10 °, specular component included), as explained in Example 1.

TABLE-US-00009 Compositions Number of shampoo washes L* a* b* ΔE Composition C 0 33.08 36.91 26.45 0 3 32.32 34.72 24.58 2.98 Composition D 0 28.16 34.61 25.12 0 3 28.93 34.54 23.19 2.08

[0555] The locks of hair pretreated with a solution of aminoalkoxysilane and dyed with compositions C or D according to the invention and washed with three shampoo washes have low ΔE values.

[0556] Thus, the coloring of the keratin fibers obtained using the compositions according to the invention shows good persistence with respect to shampoo washing. Specifically, the locks of hair dyed with the compositions according to the invention and washed with three shampoo washes show good persistence of the color.

Example 4

[0557] Solution 1 (i.e. solution of tetraethoxysilane (TEOS) and of n-octyltriethoxysilane) is prepared according to the process below: [0558] pure TEOS (reference 333859 sold by the company Sigma-Aldrich) and n-octyltriethoxysilane (reference 440213 sold by the company Sigma-Aldrich) are mixed with a solution of ethanol at pH = 3-4 and water, and said mixture is placed on a VWR brand magnetic stirrer (rotation speed 500 rpm) for 6 hours at a temperature of 50° C.

[0559] Solution 2 (i.e. solution of nonamino silicone) is prepared according to the process below: [0560] the polydimethylsiloxane (PDMS) compound bearing trialkoxysilane end functions (PDMS reference Silmer TMS Di-10 sold by the company Siltech) or the polydimethylsiloxane (PDMS) compound bearing hydroxyl end functions (PDMS reference DMS-S31 sold by the company Gelest) is diluted in an ethanol solution in which the pigment (iron oxide sold by the company Sun Chemical under the name SunPuro™ Red Iron Oxide (C33-8001)) is dispersed.

[0561] Solution 1 is mixed with solution 2 and said mixture (composition E or F depending on the nature of the nonamino silicone used) is applied to the keratin fibers.

[0562] Solution 1 alone is also applied, according to the same protocol, to the keratin fibers (composition G).

[0563] The various compounds are present in the amounts below (expressed in g/100 g).

TABLE-US-00010 Chemical name Composition E (Invention) Composition F (Invention) Composition G (comparative) Tetraethoxysilane (TEOS) 14 14 14 N-Octyltriethoxysilane 3.5 3.5 3.5 Polydimethylsiloxanes (PDMS) bearing hydroxyl end functions 12 - - Polydimethylsiloxanes (PDMS) bearing trialkoxysilane end functions - 12 - Pigment 2 2 2 Water 5.7 5.7 5.7 Ethanol qs qs qs

Protocol

[0564] Compositions E and F according to the invention and also comparative composition G are applied to locks of dry natural hair containing 90% white hairs, at a rate of 1 g of composition per gram of lock.

[0565] The locks of hair are then combed and dried with a hairdryer.

[0566] The locks of hair are left for 3 days at room temperature.

[0567] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

[0568] The shampoo wash protocol is identical to that presented in Example 2.

Results

[0569] The persistence of the color of the locks was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10 °, specular component included), as explained in Example 1.

TABLE-US-00011 Compositions Number of shampoo washes L* a* b* ΔE Composition E (Invention) 0 37.18 28.78 18.39 0 1 39.20 28.97 19.88 2.52 3 49.03 24.74 22.31 13.12 Composition F (invention) 0 34.20 31.02 18.72 0 1 37.46 30.50 20.17 3.61 3 45.50 27.41 23.12 12.65 Composition G (comparative) 0 35.29 33.51 20.39 0 1 39.64 30.53 19.82 5.30 3 52.30 21.83 17.11 20.89

[0570] The locks of hair dyed with compositions E and F according to the invention and washed with one or three shampoo washes have lower ΔE values than the locks of hair dyed with comparative composition G.

[0571] Thus, the coloring of the keratin fibers obtained using the compositions according to the invention shows good persistence with respect to shampoo washing. Specifically, the locks of hair dyed with the compositions according to the invention and washed with one or three shampoo washes show good persistence of the color.

Example 5: Pretreatment With APTES

Protocol

[0572] Before applying composition E to the keratin fibers (composition described in example 4), the locks of hair are pretreated with a solution 3 as described in example 3.

[0573] Composition E according to the invention is applied to pretreated locks of dry natural hair containing 90% white hairs, at a rate of 1 g of composition per gram of lock.

[0574] The locks of hair are then combed and dried with a hairdryer.

[0575] The locks of hair are left for three days at room temperature.

[0576] The hair is dyed uniformly and intensely.

[0577] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

[0578] The shampoo wash protocol is identical to that presented in Example 2.

Results

[0579] The persistence of the color of the locks was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10 °, specular component included), as explained in Example 1.

TABLE-US-00012 Compositions Number of shampoo washes L* a* b* ΔE Composition E + pretreatment with APTES 0 36.03 29.34 19.28 0 1 39.13 29.60 20.56 3.36 3 40.41 30.01 22.89 5.72

[0580] The locks of hair pretreated with a solution of aminoalkoxysilane, dyed with composition E according to the invention and washed with one or three shampoo washes have low ΔE values.

[0581] Thus, the coloring of the keratin fibers which is obtained using the composition according to the invention shows good persistence with respect to shampoo washing. Specifically, the locks of hair dyed wih the compositions according to the invention and washed with one or three shampoo washes show good persistence of the color.

Example 6 : Hair Coloration With and Without TEOS

[0582] The following compositions were prepared according to the protocols disclosed in the examples below The various compounds are present in the amounts below (expressed in g/100 g and active ingredients).

TABLE-US-00013 Chemical name Composition 6 (Invention) Composition 6C (Comparison) Tetraethoxysilane (TEOS) 14 - n-Octyltriethoxysilane 3.5 Polydimethylsiloxanes (PDMS) bearing hydroxyl end functions 12 Pigment 2 Water 5.7 Ethanol Qsp 100 g

[0583] Compositions 6 according to the invention and also comparative composition 6C are applied to locks of dry natural hair containing 90% white hairs, and also to locks of bleached hair, at a rate of 1 g of composition per gram of lock.

[0584] The locks of hair are then combed and dried with a hairdryer.

[0585] The locks of hair are left for 3 days at room temperature.

[0586] The locks of hair thus dyed are then subjected to a test of several repeated shampoo washes so as to evaluate the fastness (persistence) of the coloring obtained with respect to shampoo washing.

Shampoo Wash Protocol

[0587] The locks are washed with a standard shampoo (DOP).

[0588] The locks of hair are then rinsed, combed and dried with a hairdryer.

[0589] The next shampoo wash is performed on the locks obtained after the application of the hairdryer.

Results

[0590] The persistence of the color of the locks was evaluated in the CIE L* a* b* system, using a Minolta Spectrophotometer CM3600D colorimeter (illuminant D65, angle 10 °, specular component included), as explained in Example 1.

[0591] The color fastness evaluation was as followed:

TABLE-US-00014 Natural Hair with 90% white hair Compositions Number of shampoos L* a* b* ΔE Composition 6 (Invention) 0 39.1 27.01 22.06 0 1 39.82 22.28 19.62 5.4 3 40.98 20.39 18.51 7.744 Composition 6C (comparison) 0 40.27 24.35 20.98 0 1 51.97 10.76 16.7 18.444 3 57.41 7.91 20.08 23.8

TABLE-US-00015 Bleached hair Compositions Number of shampoos L* a* b* ΔE Composition 6 (Invention) 0 38.17 24.28 27.83 0 1 45.84 22.15 27.08 8.0 3 48.88 18.98 26.39 12.0 Composition 6C (comparison) 0 35.36 29.43 26.69 0 1 57.79 9.82 28.05 29.8 3 59.37 8.18 26.51 32.1

[0592] These results show that the color retention is improved with the composition of the invention over the same composition but without TEOS. The same improvement is obtained on nature and bleached hair.