Composition for dyeing keratin fibres comprising a direct dye bearing a disulphide/thiol function, a nonionic surfactant, an amphoteric surfactant, an ethoxylated fatty alcohol, an alkaline agent and a reducing agent

Patent metadata

Field	Value
Publication number	US-9265705-B2
Application number	US-201214001324-A
Country	US
Kind code	B2
Filing date	Feb 17, 2012
Priority date	Feb 25, 2011
Publication date	Feb 23, 2016
Grant date	Feb 23, 2016

Abstract

The invention relates to a process for dyeing and/or lightening keratin fibres such as the hair, using i) at least one direct dye bearing a disulfide, thiol or protected-thiol function and ii) at least one nonionic surfactant, iii) at least one amphoteric 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 fibres, 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 fibres, 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 from polymethinyl radicals of formula (VI′) below:
Ar—[C(R d )═C(R c )] m′ —W′ + -(*)Q −   (VI′)

wherein:
W′ + is chosen from divalent heterocyclic and heteroaryl radicals 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, together with the atoms that bear them, a (hetero)cycloalkyl;
Q − is an anionic counterion;
(*) represents the part of the chromophore linked to the rest of the molecule of formula (I);
Y is chosen from i) hydrogen; and ii) 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 of its 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 nonionic surfactant;
iii) at least one amphoteric 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 also esters and salts thereof, thioglycerol, cysteamine and C 1 -C 4 acyl derivatives thereof, N-mesylcysteamine, N-acetylcysteine, N-mercaptoalkylamides of sugars such as 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, mercaptoalkylamino amides, and N-mercaptoalkylalkanediamides.

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

3. The composition according to claim 2 , 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 .

4. 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, for instance phenylcarbonyl;
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 atom 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, and Z 1 is chosen from oxygen and sulfur;

sterically hindered rings; and
optionally substituted alkoxyalkyl.

5. 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.

6. The composition according to claim 1 , wherein, in formula (I), when p and p′ are equal to 1, 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) 2—; —S(O) 2 —; and —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 a cationic or non-cationic, optionally monocyclic heterocycloalkyl or heteroaryl radical, 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 — radicals 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 metal ions and ammonium groups substituted with at least one identical or different, linear or branched C 1 -C 18 alkyl radical optionally bearing at least one hydroxyl group;

z is 0 or 1.

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

wherein:
G and G′, which may be identical or different, are chosen from —NR c R d , —NR′ c R′ d and C 1 -C 6 alkoxy groups which are optionally substituted;
R c , R′ c , R d and R′ d , which may be identical or different, are chosen from hydrogen and optionally substituted aryl(C 1 -C 4 )alkyl, C 1 -C 6 alkoxy and C 1 -C 6 alkyl groups; or alternatively

Assignees

• Guerin Frédéric
• Pourille Chrystel
• Oreal

Inventors

• Guerin Frédéric
• Pourille Chrystel

Classifications

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61Q5/065

  Preparations for temporary colouring the hair, e.g. direct dyes · CPC title

• A61K8/4933 Primary

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

• A61K8/4926 Primary

  having six membered rings · CPC title

• A61K2800/4322

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