Granted Patent B2

US 8,444,711 · App. 13/397,974 · Granted May 21, 2013

Abstract

Claims (57)

1. A composition for the oxidative dyeing of keratin fibers, in particular human keratin fibers, comprising:

(A) a 1-hexyl/heptyl-4,5-diaminopyrazole compound of the general formula (I), a physiologically compatible water-soluble salt thereof, or mixtures thereof,

wherein a is equal to one or two;

wherein R 1 is selected from the group consisting of:

(a) C-linked substituents selected from the group consisting of:

(i) substituted or unsubstituted, straight or branched or cyclic, saturated or unsaturated, aliphatic or heteroaliphatic substituents, in particular alkyl or hydroxy-substituted alkyl, and

(ii) substituted or unsubstituted, mono- or poly-unsaturated aromatic or heteroaromatic substituents, in particular aryl or heteroaryl,

wherein said C-linked substituents comprise from 1 to 6 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of O, F, N, P and Si;

(b) S-linked substituents selected from the group consisting of SA 1 , SO 2 A 1 , SO 3 A 1 , SSA 1 , SOA 1 , SO 2 NA 1 A 2 , SNA 1 A 2 , and SONA 1 A 2 ;

(c) O-linked substituents selected from the group consisting of OA 1 and ONA 1 A 2 ;

(d) N-linked substituents selected from the group consisting of NA 1 A 2 ; (NA 1 A 2 A 3 ) + , NA 1 SA 2 , NO 2 ; and NA 1 A 2 ;

(e) halogens selected from the group consisting of F, Cl, Br, and I; and

(f) hydrogen;

wherein A 1 , A 2 , and A 3 are selected independently from each other from the group consisting of: hydrogen; substituted or unsubstituted, straight or branched or cyclic, saturated or unsaturated, aliphatic or heteroaliphatic or aromatic or heteroaromatic substituents, or A 1 and A 2 together with nitrogen atoms to which they are bound form a ring; wherein said substituents or ring comprise from 1 to 6 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;

wherein R 2 and R 3 are selected independently of each other from the group consisting of a hydrogen atom; a C1-C6 alkyl substituent; a trifluoromethyl substituent; a C1-C6 aminoalkyl substituent; a C1-C6 hydroxyalkyl substituent; and C1-C6 an alkoxyalkyl substituent;

(B) a benzene-1,3-diamine compound of the general formula (II), a physiologically compatible water-soluble salt thereof, or mixtures thereof,

wherein R 4 , R 5 , R 6 , R 7 are substituents selected independently of each other from the group consisting of:

(a) C-linked substituents selected from the group consisting of:

(i) substituted or unsubstituted, straight or branched or cyclic, saturated or unsaturated, aliphatic or heteroaliphatic substituents, in particular alkyl or hydroxy substituted alkyl, and

(ii) substituted or unsubstituted, mono- or poly-unsaturated aromatic or heteroaromatic substituents, in particular aryl or heteroaryl,

wherein said C-linked substituents comprise from 1 to 10 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of O, F, N, P and Si;

(b) S-linked substituents selected from the group consisting of SA 1 , SO 2 A 1 , SO 3 A 1 , SSA 1 , SOA 1 , SO 2 NA 1 A 2 , SNA 1 A 2 , and SONA 1 A 2 ;

(c) O-linked substituents selected from the group consisting of OA 1 and ONA 1 A 2 ;

(d) N-linked substituents selected from the group consisting of NA 1 A 2 ; (NA 1 A 2 A 3 ) + , NA 1 SA 2 , NO 2 ; and NA 1 A 2 ;

(e) halogens selected from the group consisting of F, Cl, Br, and I; and

(f) hydrogen;

wherein A 1 , A 2 , and A 3 are selected independently of each other from the group consisting of: hydrogen; substituted or unsubstituted, straight or branched or cyclic, saturated or unsaturated, aliphatic or heteroaliphatic or aromatic or heteroaromatic substituents, or A 1 and A 2 together with nitrogen atoms to which they are bound form a ring; wherein said substituents or ring comprise from 1 to 10 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of O, S, N, P, and Si;

wherein R 8 and R 9 are substituents selected independently of each other from the group consisting of:

(g) C-linked substituents selected from the group consisting of:

(i) substituted or unsubstituted, straight or branched or cyclic, saturated or unsaturated, aliphatic or heteroaliphatic substituents, in particular alkyl or hydroxy substituted alkyl, and

(ii) substituted or unsubstituted, mono- or poly-unsaturated aromatic or heteroaromatic substituents, in particular aryl or heteroaryl,

wherein said C-linked substituents comprise from 1 to 6 carbon atoms and from 0 to 5 heteroatoms selected from the group consisting of O, F, N, P and Si; and

(h) hydrogen; and

(C) an oxidizing agent.

2. A composition according to claim 1 wherein R 5 is hydrogen or C2-C6 hydroxyalkoxy, R 4 and R 6 are independently selected from hydrogen, halogens, C1-C6 alkyl and C2-C6 hydroxalkyl, C2-C6 hydroxyalkoxy, C1-C4 alkoxy, and O(CH2)nO-Ph(2,4-diamino) wherein n is equal to 2 or 3, R 7 is selected from hydrogen, halogens, C1-C6 alkyl and C2-C6 hydroxalkyl, C1-C4 alkoxy and mixtures thereof and R 8 and R 9 are independently selected from hydrogen, C1-C3 alkyl or C1-C3 hydroxyalkyl, C1-C4 alkoxyalkyl and mixtures thereof, or NR 8 R 9 forms a pyrrolidine or piperidine ring.

3. A composition according to claim 1 , wherein the 1-hexyl/heptyl-4,5-diaminopyrazole compound (I) is a compound with formula (I.1):

4. A composition according to claim 1 , further comprising a primary intermediate selected from toluene-2,5-diamine, p-phenylenediamine, 2-hydroxyethyl-p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, 2-(2,5-diamino-4-methoxyphenyl)propane-1,3-diol, 2-chloro-p-phenylenediamine, 2-methoxy-p-phenylenediamine, 2-((2-(4-amino-phenylamino)-ethyl)-(2-hydroxyethyl)-amino)-ethanol, salts thereof and combination thereof.

5. A composition according to claim 1 , wherein the benzene-1,3-diamine compound (II) is selected from the group consisting of compounds (II.1) to (II.4) and combinations thereof:

6. A composition according to claim 1 , further comprising at least one auxiliary coupler selected from the group consisting of compounds with formula (III.1) to (III.8) below:

7. A composition according to claim 1 , further comprising fatty alcohols comprising from 14 to 30 carbon atoms, or oxyethylenated fatty alcohols comprising from 16 to 30 carbon atoms and 2 units or less of ethylene oxide.

8. A composition according to claim 7 , further comprising at least one ionic or nonionic surfactant selected from:

anionic surfactants selected from C8-C30 alkyl sulfates,

anionic surfactants according to the formula R n X m YM, wherein R is independently selected from alkyl, alkenyl or alkylaryl groups having from 8 to 30 carbon atoms, X is independently selected from polar groups comprising at least one carbon atom and at least one oxygen or nitrogen atom, Y is an anionic group selected from carboxylates, sulfates, sulfonates or phosphates, n and m are independently 1 or 2, and M is hydrogen or a salt forming cation and mixture thereof;

non-ionic surfactant comprising one or more polyethyleneoxide chains;

cationic surfactants selected from quaternary ammonium salts or amido-amines having at least one fatty chain; and

mixtures thereof.

9. A composition according to claim 8 comprising a mixture of cetearyl alcohol and dicetyl phosphate and ceteth-10 phosphate.

10. A composition according to claim 1 further comprising a chelant selected from the group consisting of: diethylenetriamine-N,N′,N″-polyacids, diethylenetriaminepentaacetic acid (DTPA), diethylenetriaminepenta(methylene phosphonic acid) (DTPMP), diamine-N,N′-dipolyacid, monoamine monoamide-N,N′-dipolyacid, and N,N′-bis(2-hydroxybenzyl)ethylenediamine-N,N′-diacetic acid chelants, carboxylic acids, phosphonic acids and polyphosphoric acids, their salts and derivatives.

11. A composition according to claim 1 wherein said oxidizing agent is selected from the group consisting of hydrogen peroxide, sodium periodate, urea peroxide, melamine peroxide, perborates, percarbonates, perphosphates, persilicates, persulfates, oxidizing enzymes such as uricases, oxidases, and peroxidases, a source of peroxymonocarbonate ions and mixtures thereof.

12. A composition according to claim 1 , wherein said composition is dispensed as a foam.

13. A method of dyeing hair comprising the steps of:

(i) providing a tint component comprising (a) a 1-hexyl/heptyl-4,5-diaminopyrazole compound of the general formula (I) as defined in claim 1 , a physiologically compatible, water-soluble salt thereof or mixtures thereof and; (b) a benzene-1,3-diamine compound of the general formula (II) as defined in claim 1 , a physiologically compatible water-soluble salt thereof or mixtures thereof;

(ii) providing a developer component comprising (c) an oxidizing agent;

(iii) mixing the tint component and the developer component to obtain a composition for the oxidative dyeing of keratin fibers according to claim 1 ; and

(iv) applying said composition for the oxidative dyeing of keratin fibers onto the hair.

14. An oxidative hair dyeing kit comprising: (i) a tint component comprising (a) a 1-hexyl/heptyl-4,5-diaminopyrazole compound of the general formula (I) as defined in claim 1 , a physiologically compatible water-soluble salt thereof or mixtures thereof and, (b) a benzene-1,3-diamine of the general formula (II) as defined in claim 1 , a physiologically compatible water-soluble salt thereof or mixtures thereof; and ii) a developer component comprising an oxidizing agent.

15. A tint component comprising (a) a 1-hexyl/heptyl-4,5-diaminopyrazole compound of the general formula (I) as defined in claim 1 , a physiologically compatible, water-soluble salt thereof or mixtures thereof, and (b) a benzene-1,3-diamine compound of the general formula (II) as defined in claim 1 , a physiologically compatible water-soluble salt thereof or mixtures thereof.

Assignments (7)