Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a sparingly or non-ethoxylated fatty alcohol, a cationic surfactant, an alkaline agent and a reducing agent

Patent metadata

Field	Value
Publication number	US-9345652-B2
Application number	US-201214001318-A
Country	US
Kind code	B2
Filing date	Feb 17, 2012
Priority date	Feb 25, 2011
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

The invention relates to a process for dyeing and/or lightening keratin fibers such as the hair, using i) at least one direct dye bearing a disulfide, thiol or protected-thiol function and ii) at least one sparingly or non-ethoxylated fatty alcohol, iii) at least one cationic surfactant, iv) at least one alkaline agent, and v) at least one reducing agent. The invention also relates to a composition comprising the ingredients i) to v), to the use of the combination of i), ii), iii), iv) and v) for the dyeing and/or lightening of keratin fibers, and to a multi-compartment kit comprising the ingredients i) to v). The dyeing process and the composition according to the invention especially afford a long-lasting coloration on keratin fibers, which is strong, chromatic and/or homogeneous, with or without the use of an oxidizing agent.

First claim

The invention claimed is:

1. A cosmetic composition comprising:
i) at least one direct dye chosen from dyes of formula (I) comprising at least one functional group chosen from disulfide, thiol, and protected-thiol functional groups:
A-(X) p —C sat —S—U  (I)

the salts thereof with an organic or mineral acid, optical or geometric isomers thereof, tautomers thereof, and solvates thereof,
wherein:
U is a radical chosen from:
a) —S—C′ sat —(X′) p′ -A′; and
b) —Y;

A and A′, which may be identical or different, are chosen polymethine radicals of formula (VI′), below:
Ar—[C(R d )═C(R c )] m′ —W′ + —(*)Q −   (VI′)

wherein:
W + is chosen from cationic heterocyclic and heteroaryl groups;
Ar is an optionally substituted aryl group;
m′ is an integer ranging from 1 to 4 inclusive;
R c and R d , which may be identical or different, are chosen from hydrogen and optionally substituted (C 1 -C 8 )alkyl groups, or alternatively R c contiguous with W′ + and/or R d contiguous with Ar form, with the atoms that bear them, a (hetero)cycloalkyl;
Q − is an anionic counterion;
(*) is the part of the chromophore linked to the rest of the molecule of formula (I);
Y is chosen from hydrogen and thiol-function protecting groups;
X and X′, which may be identical or different, are chosen from linear or branched, saturated or unsaturated divalent C 1 -C 30 hydrocarbon-based chains, optionally interrupted and/or optionally terminated at one or both ends with at least one divalent group chosen from:
—N(R)—, —N + (R)(R)—, —O—, —S—, —CO—, and —SO 2 —, wherein R, which may be identical or different, is chosen from hydrogen and C 1 -C 4 alkyl, hydroxyalkyl and aminoalkyl radicals;
aromatic or non-aromatic, saturated or unsaturated, fused or non-fused (hetero)cyclic radicals optionally comprising at least one identical or different, optionally substituted heteroatom;

p and p′, which may be identical or different, are equal to 0 or 1;
C sat and C sat , which may be identical or different, are chosen from optionally cyclic, optionally substituted linear or branched C 1 -C 18 alkylene chains;

ii) at least one fatty alcohol chosen from sparingly ethoxylated and non-ethoxylated fatty alcohols;
iii) at least one cationic surfactant;
iv) at least one alkaline agent; and
v) at least one reducing agent chosen from thioglycolic acid, thiolactic acid, 3-mercaptopropionic acid, thiomalic acid, 2,3-dimercaptosuccinic acid, cysteine, N-glycyl-L-cysteine, L-cysteinylglycine, and esters and salts thereof; thioglycerol; cysteamine and C 1 -C 4 acyl derivatives thereof; N-mesylcysteamine; N-acetylcysteine; N-(mercapto-2-ethyl) gluconamide; pantetheine, N-(mercaptoalkyl)-ω-hydroxyalkylamides; N-mono- or N,N-dialkylmercapto-4-butyramides; aminomercaptoalkyl amides; N-(mercaptoalkyl)succinamic acids and N-(mercaptoalkyl)succinimides; alkylamino mercaptoalkyl amides; the azeotropic mixture of 2-hydroxypropyl thioglycolate and of (2-hydroxy-1-methyl)ethyl thioglycolate; ammonium thioglycolate; mercaptoalkylamino amides; and N-mercaptoalkylalkanediamides.

2. The composition according to claim 1 , wherein the radicals A and/or A′ of the at least one direct dye of formula (I), which may be identical or different, are chosen from radicals comprising at least one quaternized cationic chromophore.

3. The composition according to claim 1 , wherein which the at least one direct dye of formula (I) is a disulfide dye, wherein U is a radical chosen from a) —S—C′ sat —(X′) p′ -A′.

4. The composition according to claim 3 , wherein the at least one direct dye of formula (I) is a symmetrical disulfide dye of the following formula (Ia):
A-(X) p —C sat —S—S—C′ sat —(X′) p′ -A′  (Ia)

wherein A=A′, X=X′, p=p′, and C sat =C′ sat .

5. The composition according to claim 1 , wherein the at least one direct dye of formula (I) is a dye comprising a thiol or protected-thiol function, wherein U is the radical b) Y, chosen from hydrogen and the following radicals:
(C 1 -C 4 )alkylcarbonyl;
(C 1 -C 4 )alkylthiocarbonyl;
(C 1 -C 4 )alkoxycarbonyl;
(C 1 -C 4 )alkoxythiocarbonyl;
(C 1 -C 4 )alkylthio-thiocarbonyl;
(di)(C 1 -C 4 )(alkyl)aminocarbonyl;
(di)(C 1 -C 4 )(alkyl)aminothiocarbonyl;
arylcarbonyl;
aryloxycarbonyl;
aryl(C 1 -C 4 )alkoxycarbonyl;
(di)(C 1 -C 4 )(alkyl)aminocarbonyl;
(C 1 -C 4 )(alkyl)arylaminocarbonyl;
carboxyl;
SO 3 − M + , wherein M + is chosen from alkali metal ions, or alternatively a counterion of the cationic chromophore A and M + are absent;
optionally substituted aryl;
optionally substituted heteroaryl;
optionally cationic, optionally substituted heterocycloalkyl;
—C(NR′ c R′ d )═N + R′ e R′ f ; An′″ − , wherein R′ c , R′ d , R′ e and R′ f , which may be identical or different, are chosen from hydrogen and (C 1 -C 4 )alkyl groups and An′″ − is a counterion;
—C(NR′ c R′ d )═NR′ e ; wherein R′ c , R′ d and R′ e are defined above;
optionally substituted (di)aryl(C 1 -C 4 )alkyl;
optionally substituted (di)heteroaryl(C 1 -C 4 )alkyl;
CR 1 R 2 R 3 , wherein R 1 , R 2 and R 3 , which may be identical or different, are chosen from halogen and the following groups:
(C 1 -C 4 )alkyl;
(C 1 -C 4 )alkoxy;
optionally substituted aryl;
optionally substituted heteroaryl;
—P(Z 1 )R′ 1 R′ 2 R′ 3 , wherein R′ 1 and R′ 2 , which may be identical or different, are chosen from hydroxyl, (C 1 -C 4 )alkoxy and alkyl groups, R′ 3 is chosen from hydroxyl and (C 1 -C 4 )alkoxy groups, and Z 1 is chosen from oxygen and sulfur;

sterically hindered rings; and
optionally substituted alkoxyalkyl.

6. The composition according to claim 1 , wherein, in formula (I), C sat and C′ sat , which may be identical or different, are chosen from —(CH 2 ) k — chains, wherein k is an integer ranging from 1 to 8 inclusive.

7. The composition according to claim 1 , wherein, in formula (I), p and p′ are equal to 1, and X and X′, which may be identical or different, are chosen from the following sequence:
-(T) t -(Z) z -(T) t′ -
wherein the sequence is linked in formula (I) symmetrically as follows:
—C sat (or C′sat)-(T) t -(Z) z -(T′) t′ -(A or A′);

wherein:
T and T′, which may be identical or different, are chosen from at least one of: —O—; —S—; —N(R)—; —N+(R)(R o )—; —S(O)—; —S(O) 2 —; —C(O)—; wherein R, R o , which may be identical or different, are chosen from hydrogen, C 1 -C 4 alkyl radicals, C 1 -C 4 hydroxyalkyl radicals and aryl(C 1 -C 4 )alkyl radicals; and cationic or non-cationic heterocycloalkyl or heteroaryl radicals, optionally monocyclic and optionally comprising two heteroatoms;
t and t′, which may be identical or different, are equal to 0 or 1;
Z is chosen from:
—(CH 2 ) m —, wherein m is an integer ranging from 1 to 8 inclusive;
—(CH 2 CH 2 O) q — and —(OCH 2 CH 2 ) q —, wherein q is an integer ranging from 1 to 5 inclusive;
aryl, alkylaryl and arylalkyl radicals, wherein the alkyl radical is chosen from C 1 -C 4 alkyl radicals, optionally substituted with at least one group SO 3 M, wherein M is chosen from hydrogen, alkali metals and ammonium groups substituted with at least one radical, which may be identical or different, chosen from linear or branched C 1 -C 18 alkyl radicals optionally bearing at least one hydroxyl group; and

z is 0 or 1.

8. The composition according to claim 1 , wherein the at least one dye of formula (I) is chosen from disulfide dyes of formulae XII and thiol or protected-thiol dyes of formulae XII′ below:

Assignees

• Pourille Chrystel
• Oreal

Inventors

• Pourille Chrystel

Classifications

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61K8/4933 Primary

  having sulfur as an exocyclic substituent, e.g. pyridinethione · CPC title

• A61K8/416

  Quaternary ammonium compounds (A61K8/35 takes precedence) · CPC title

• A61K2800/4322

  in preparations for temporarily coloring the hair further containing an oxidizing agent · CPC title

• A61K8/342

  Alcohols having more than seven atoms in an unbroken chain · CPC title