Composition for dyeing keratinous fibres comprising a direct dye having a disulphide/thiol functional group, a thickening polymer, an ethoxylated fatty alcohol and/or a nonionic surfactant, an alkaline agent and a reducing agent

Patent metadata

Field	Value
Publication number	US-9522106-B2
Application number	US-201214001321-A
Country	US
Kind code	B2
Filing date	Feb 17, 2012
Priority date	Feb 25, 2011
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

A subject-matter of the invention is a method for dyeing and/or lightening keratinous fibres, such as the hair, employing i) at least one direct dye having a disulphide, thiol or protected thiol functional group and ii) at least one thickening organic polymer, iii) at least one (poly)ethoxylated fatty alcohol and/or one nonionic surfactant, iv) at least one alkaline agent and v) at least one reducing agent. Another subject-matter of the invention is a composition comprising the ingredients i) to v), the use of the combination of i), ii), iii), iv) and v) for dyeing and/or lightening keratinous fibres and a multicompartment kit comprising the ingredients i) to v). The dyeing method and the composition according to the invention make it possible in particular to obtain a lasting coloration on keratinous fibres which is intense, 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 disulphide, thiol and protected thiol functional groups:
A-(X) p —C sat —S—U  (I)

 the salts thereof with an organic or inorganic acid, the optical or geometric isomers thereof, the tautomers thereof, and the 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 alternative R c contiguous with W′ + and/or R d contiguous with Ar form, with the atoms that bear them, a (hetero)cycloalkvl;
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 i) hydrogen and ii) protective groups for the thiol functional group;
X and X′, which may be identical or different, are chosen from saturated or unsaturated and linear or branched divalent C 1 -C 30 hydrocarbon chains optionally interrupted and/or optionally terminated at one or both ends by 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, C 1 -C 4 alkyl radicals, hydroxyalkyl radicals and aminoalkyl radicals;
fused or nonfused, saturated or unsaturated and aromatic or nonaromatic (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 linear or branched C 1 -C 18 alkylene chains which may be optionally substituted and optionally cyclic;

ii) at least one thickening organic polymer;
iii) at least one (poly)ethoxylated fatty alcohol and/or at least one nonionic 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 disulphide 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 disulphide dye of 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 functional group, 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 else a counterion of the cationic chromophore A and M + are absent;
optionally substituted aryl;
optionally substituted heteroaryl;
optionally substituted heterocycloalkyl which is optionally cationic;
—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 atoms and the following groups:
(C 1 -C 4 )alkyl;
(C 1 -C 4 )alkoxy;
optionally substituted aryl;
optionally substituted heteroaryl; and
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 sulphur;

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), 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 symmetrically connected in the formula (I) 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.)—; —S(O)—; —S(O) 2 —; and —C(O)—; wherein R and R., which may be identical or different, are chosen from hydrogen; C 1 -C 4 alkyl radicals; C 1 -C 4 hydroxyalkyl radicals; aryl(C 1 -C 4 )alkyl radicals; and cationic or noncationic, 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 by at least one SO 3 M group, wherein M is chosen from hydrogen, alkali metals, and ammonium groups substituted by at least one radical, which may be identical or different, chosen from linear or branched C 1 -C 18 alkyl radicals optionally carrying 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:

wherein:
G and G′, which may be identical or different, are c

Assignees

• Guerin Frédéric
• Pourille Chrystel
• Oreal

Inventors

• Guerin Frédéric
• Pourille Chrystel

Classifications

• A61K8/4926

  having six membered rings · CPC title

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61Q5/065

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

• A61K8/49

  containing heterocyclic compounds · CPC title

• A61K8/731

  Cellulose; Quaternized cellulose derivatives · CPC title