Dyeing composition at acidic pH comprising a direct dye of triarylmethane structure

Abstract

The present invention relates to a composition for dyeing keratin fibres comprising, in a cosmetically acceptable medium of acidic pH, the pH of which is preferably less than 5, one or more direct dyes of triarylmethane structure, which are preferably cationic. The invention also relates to a process for dyeing keratin fibres using said composition and also to a use for dyeing keratin fibres.

Claims

1. A process for dyeing human hair, comprising: applying to human hair a composition comprising, in a cosmetically acceptable medium of acidic pH less than 5, at least one cationic direct dye of triarylmethane structure.

2. The process according to claim 1, wherein the pH of the composition ranges from 1 to 4.9.

3. The process according to claim 1, wherein the cationic direct dye of triarylmethane structure is chosen from the cationic dyes of formula (I) ##STR00042## or the organic or mineral, acid or base addition salts thereof, the geometrical isomers, optical isomers, or tautomers thereof, the mesomeric forms thereof, or the solvates or hydrates thereof; wherein in formula (I): A, B and C are identical or different, and each represents a (hetero)aryl group which is optionally substituted, and ═ represents a single bond or a double bond.

4. The process according to claim 1, wherein the cationic direct dye of triarylmethane structure is chosen from the cationic dyes of formulae (IIa) and (II′a) below: ##STR00043## or the organic or mineral, acid or base addition salts thereof, the geometrical isomers, optical isomers, or tautomers thereof, the mesomeric forms thereof, or the solvates or hydrates thereof: wherein in formulae (IIa) and (II′a) below: R1, R2, R3 and R4, which may be identical or different, each represents a hydrogen atom or a (C1-C6)alkyl group which is optionally substituted with a hydroxyl group, an aryl group, phenyl, an aryl(C1-C4)alkyl group, benzyl, a heteroaryl, or a heteroaryl(C1-C4)alkyl group, or else two groups R1 and R2, and/or R3 and R4, borne by the same nitrogen atom, form, together with the nitrogen atom which bears them, an optionally substituted heterocycloalkyl group, morpholino, piperazino, or piperidino; R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16, which may be identical or different, each represents a hydrogen atom, a halogen atom, or a group chosen from i) hydroxyl; ii) thiol; iii) amino; iv) (di)(C1-C4)(alkyl)amino; v) (di)arylamino or (di)phenylamino; vi) nitro; vii) acylamino (—NR—C(O)R′) in which the radical R is a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group, and the radical R′ is a C1-C2 alkyl radical; viii) carbamoyl ((R).sub.2N—C(O)—) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group; ix) carboxylic acid or ester, (—O—C(O)R′) or (—C(O)OR′), in which the radical R′ is a hydrogen atom, or C1-C4 alkyl optionally bearing at least one hydroxyl group and the radical R′ is a C1-C2 alkyl radical; x) alkyl optionally substituted in particular with a hydroxyl group; xi) alkylsulfonylamino (R′SO.sub.2—NR—) in which the radical R represents a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the radical R′ represents a C1-C4 alkyl radical or a phenyl radical; xii) aminosulfonyl ((R).sub.2N—SO2-) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group; xiii) (C1-C4)alkoxy; or xiv) (C1-C4)alkylthio; or else two radicals borne by two contiguous carbon atoms R5 and R6 and/or R7 and R8 and/or R9 and R10 and/or R11 and R12 and/or R13 and R14 and/or R15 and R16 form, together with the carbon atoms which bear them, an aryl or heteroaryl, said ring being optionally substituted; Q- represents an anionic counterion for achieving electroneutrality.

5. The process according to claim 1, wherein the cationic direct dye of triarylmethane structure is chosen from those of formula (IIa) or (II′a), wherein, taken together or separately: R1, R2, R3 and R4 each represents a hydrogen atom, a (C1-C4)alkyl group, methyl, or ethyl, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, and R16 each represents a hydrogen atom, a halogen atom, chlorine, a (C1-C4)alkyl group, methyl, ethyl, an amino group, or a (di)(C1-C4)(alkyl)amino group.

6. The process according to claim 1, wherein the cationic direct dye of triarylmethane structure is chosen from Basic Violet 1, Basic Violet 2, Basic Violet 3, Basic Violet 4, Basic Violet 14, Basic Blue 1, Basic Blue 7, Basic Blue 26, Basic Green 1, Basic Blue 77, or mixtures thereof.

7. The process according to claim 1, wherein the total amount of cationic direct dye of triarylmethane structure ranges from 0.0001% to 10% by weight, relative to the total weight of the composition.

8. The process according to claim 1, wherein the composition further comprises at least one amino silicone, chosen from the silicones of formula (B) below:
R′aG3-a-Si(OSiG2)n-(OSiGbR′2-b)m-O—SiG3-a-R′a  (B) wherein: G, which may be identical or different, denotes a hydrogen atom or a phenyl, OH, C.sub.1-C.sub.8 alkyl, methyl, C.sub.1-C.sub.8 alkoxy, or methoxy group, a, which may be identical or different, represents 0 or an integer from 1 to 3, b denotes 0 or 1, m and n are numbers such that the sum (n+m) ranges from 1 to 2000, wherein n represents a number from 0 to 1999 and m represents a number from 1 to 2000; R′, which may be identical or different, represents a monovalent radical of formula —CqH2qL in which q is a number ranging from 2 to 8 and L is an optionally quaternized amino group chosen from —N(R″)2; —N+(R″)3 A-; —NR″-Q-N(R″)2, or —NR″-Q-N+(R″)3 A-, wherein: R″, which may be identical or different, represents hydrogen, phenyl, benzyl, a saturated monovalent hydrocarbon-based radical, a C1-C20 alkyl radical; Q denotes a linear or branched CrH2r group, r being an integer ranging from 2 to 6; and A- represents a cosmetically acceptable anion, a halide, fluoride, chloride, bromide, or iodide.

9. The process according to claim 8, wherein the amino silicone is chosen from the silicones of formula (F) below: ##STR00044## wherein: m and n are numbers such that the sum (n+m) ranges from 1 to 2000, wherein n represents a number from 0 to 1999, and m represents a number from 1 to 2000; A denotes a linear or branched alkylene radical containing from 4 to 8 carbon atoms.

10. The process according to claim 8, wherein the total amount of the amino silicone ranges from 0.01% to 10% by weight, relative to the total weight of the composition.

11. The process according to claim 1, wherein the composition comprises at least one surfactant.

12. The process according to claim 11, wherein the at least one surfactant is chosen from cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxyethylmethylammonium salts, and mixtures thereof.

13. The process according to claim 1, further comprising at least one fatty substance in a total amount of greater than or equal to 3% by weight, relative to the total weight of the composition.

14. The process according to claim 1, further comprising at least one additive chosen from a thickening polymer, a cationic polymer, an additional direct dye other than the dyes of triarylmethane structure, or mixtures thereof.

15. The process according to claim 12, wherein the surfactant is chosen from behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and dipalmitoylethyl-hydroxyethylmethylammonium methosulfate, and mixtures thereof.

Description

EXAMPLES

(1) In the examples that follow, the colour build-up (ΔE.sub.ab*) was evaluated in the CIE L*a*b* system.

(2) In this L*a*b* system, L* represents the intensity of the colour, a* indicates the green/red colour axis and b* the blue/yellow colour axis. The lower the value of L*, the darker or more intense the colour.

(3) The value of ΔE.sub.ab* was calculated from the values of L*a*b* according to equation (i) below:
ΔE.sub.ab*=√{square root over ((L*−L.sub.o*).sup.2+(a*−a.sub.o*).sup.2+(b*−b.sub.o*).sup.2)}  (i)

(4) The colour build-up (ΔE.sub.Lab*) was calculated from the colorimetric values for locks of untreated hair (L.sub.0*, a.sub.0* and b.sub.0*) and locks of dyed hair (L*, a* and b*).

(5) The greater the value of ΔE.sub.ab*, the better the colour build-up for the treated fibres.

(6) In the examples that follow, all the amounts are given as weight percentages of active materials relative to the total weight of the composition, unless otherwise indicated.

I. Example 1

(7) a. Compositions Tested

(8) Compositions (A1), (B1), (A2) and (B2) below were prepared from the ingredients as described below, the contents of which are indicated in gram % (unless otherwise mentioned) in Table 1 below.

(9) Compositions A1 and B1 are compositions according to the invention, the pH of which is acidic (pH 3.5), and comprising respectively the cationic direct dyes of triarylmethane structure Basic Blue 77 (also known as HC Blue 15) and Basic Violet 2.

(10) Compositions A2 and B2 are comparative compositions outside the invention, the pH of which is basic (pH 9).

(11) TABLE-US-00001 TABLE 1 A1 A2 B1 B2 Inven- Compar- Inven- Compar- tion ative tion ative Sodium hydroxide pH = 3.5 pH = 9 pH = 3.5 pH = 9 Citric acid 0.025 0.025 0.025 0.025 Basic Blue 77 0.2 0.2 — — (HC Blue No. 15) Basic Violet 2 — — 0.1 0.1 Cetylstearyl Alcohol 3.75 3.75 3.75 3.75 (50/50 C16/C18) Cetyl Alcohol 1 1 1 1 Hydroxyethylcellulose 0.2 0.2 0.2 0.2 (MW: 1 300 000 Hydroxypropyl guar 0.1 0.1 0.1 0.1 trimethylammonium chloride Polydimethylsiloxane 2 2 2 2 containing aminoethyl aminopropyl groups, containing methoxy and/ or hydroxyl and alpha- omega silanol functions, as a cationic 60% aqueous emulsion (1) Deionized water qs 100 qs 100 qs 100 qs 100 Preservatives qs qs qs qs Behenyltrimethyl- 2.6 2.6 2.6 2.6 ammonium chloride as an aqueous solution containing 79% am

(12) (1) Amodimethicone (and) Trideceth-6 (and) cetrimonium chloride sold under the reference Xiameter MEM-8299 Emulsion by Dow Corning

(13) b. Direct Dyes Tested

(14) The direct dyes used in compositions (A1), (B1), (A2) and (B2) are indicated in Table 2 below.

(15) TABLE-US-00002 TABLE 2 BASIC BLUE 77 (HC BLUE No 15) BASIC VIOLET 2

(16) c. Procedure

(17) Compositions A1, A2, B1 and B2 are applied to locks of hair that is very sensitized owing to bleaching, in a proportion of 5 g of composition per 1 g of hair.

(18) After a leave-on time of 20 minutes at ambient temperature, the locks are rinsed with clear water, then dried.

(19) d. Evaluation

(20) The colorimetric measurements are performed using a Minolta CM2006D spectrocolorimeter (illuminant D65, angle 10°, specular component included) in the CIELab system.

(21) e Results

(22) The results are reported in Table 3 below.

(23) TABLE-US-00003 TABLE 3 L* B1 - BV2 pH 3.5 31.42 B2 - BV2 pH 9 36.22 A1 - BV77 pH 3.5 26.93 A2 - BV77 pH 9 34.56

(24) The power is represented by the value of L*: the lower the value of L*, the more powerful the colour obtained.

(25) As shown by the table above, the compositions according to the invention (A1 and B1) formulated at acidic pH allowing much greater colour power obtained at acidic pH.

II. Example 2

(26) a Compositions Tested

(27) Compositions (C1), (C2) and (D) below were prepared from the ingredients as described below, the contents of which are indicated in gram % (unless otherwise mentioned) in Table 4 below.

(28) Compositions C1 and C2 are compositions according to the invention, the pH of which is acidic, and comprising respectively the cationic direct dyes of triarylmethane structure Basic Blue 77 (also known as HC Blue 15) and Basic Blue 1. Composition D is a comparative composition outside the invention, the pH of which is acidic, but which comprises as direct dye Basic Blue 99 which is not a direct dye of triarylmethane structure.

(29) TABLE-US-00004 TABLE 4 C1 C2 D (invention) (invention) (comparative) Sodium Hydroxide pH = 3.5 pH = 3.5 pH = 3.5 Basic Blue 77 (HC Blue 0.5 — — No. 15) Basic Blue 1 — 0.5 — Basic Blue 99 — — 0.5 Cetyl alcohol 0.95 0.95 0.95 Guar 0.1 0.1 0.1 Hydroxypropyltrimonium Chloride Cetearyl Alcohol 3.75 3.75 3.75 Preservative qs qs qs Amodimethicone 1.15 1.15 1.15 Behentrimonium Chloride 2 2 2 Citric acid 0.025 0.025 0.025 Hydroxyethylcellulose 0.2 0.2 0.2 Water qs 100 qs 100 qs 100

(30) e. Direct Dyes Tested

(31) The direct dyes used in compositions (C1), (C2) and (D) are indicated in the table below:

(32) TABLE-US-00005 Basic Blue 77 (HC Blue No 15) 0 Basic Blue No 1 Basic Blue 99

(33) f. Procedure

(34) Compositions C1, C2 and D are applied to locks of natural hair containing 90% grey hairs, in a proportion of 5 g per gram of hair.

(35) After a leave-on time of 20 minutes at ambient temperature, the locks are rinsed with clear water, then dried.

(36) g. Evaluation

(37) The colorimetric measurements are performed using a Minolta CM2006D spectrocolorimeter (illuminant D65, angle 10°, specular component included) in the CIELab system.

(38) h. Results

(39) The results are reported in Table 5 below.

(40) TABLE-US-00006 TABLE 5 L* a* b* ΔE Non-dyed hair 63.66 2.07 16.43 C1 25.31 5.55 −32.55 62.30 (invention) C2 23.49 −16.61 −13.78 53.62 (invention) D 21.24 1.24 −7.46 48.96 (comparative)

(41) Compositions C1 and C2 according to the invention result in a better buildup of the colour compared with comparative composition D.