IP Library › Granted Patent US 8,366,792
Granted Patent B2
US 8,366,792 · App. 13/389,832 · Granted Feb 5, 2013

Dye composition comprising a heterocyclic oxidation base and an indole coupler

Inventors: Anne-Marie Couroux (Saint-Ouen-d'Aunis, FR); Aziz Fadli (Chelles, FR)
Assignee: L'OREAL
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Quick Facts
Patent No.
US 8,366,792
App. No.
13/389,832
Granted
Feb 5, 2013
Kind
B2
Abstract

The subject of the present invention is dye composition for keratin fibers, comprising, in suitable dyeing medium, a coupler of formula (I) or addition salts thereof with an acid a particular cationic or noncationic aminopyrazolopyridine derivative. The composition of the present invention makes it possible in particular to obtain a coloring with varied, intense and/or chromatic, aesthetic and relatively nonselective shades which are highly resistant to the various attacks to which the hair may be subjected.

Claims (51)

1. Dye composition for keratin fibres, comprising, in a suitable dyeing medium,

a coupler of formula (I) or addition salts thereof with an acid

one or more heterocyclic oxidation bases chosen from the aminopyrazolopyridine bases of formula (II) or (III) and the diamino-N,N-dihydropyrazolone bases of formula (IV),

in which:

R 1 , R 2 , R 3 , R 4 and R 5 , which may be identical or different, represent a hydrogen or halogen atom; an —NHSO 3 H radical; a hydroxyl radical; a (C 1 -C 4 ) alkyl radical; a (C 1 -C 4 ) alkoxy radical; a (C 1 -C 4 ) alkylthioradical; mono (C 1 -C 4 ) alkylamino; a di (C 1 -C 4 ) alkylamino radical in which the two alkyl groups can, together with the nitrogen atom to which they are attached, form a ring which can be interrupted with one or more nitrogen, oxygen or sulphur atoms; a heterocycle; a nitro radical; a phenyl radical; a carbonyl radical; a (C 1 -C 4 ) alkoxycarbonyl radical; a carboxamido radical; a cyano radical; an amino radical; a sulphonyl radical; a —CO 2 H radical, an —SO 3 H radical; a —PO 3 H 2 radical; a —PO 4 H 2 radical; or a group:

in which R′″ represents an oxygen or nitrogen atom, Q represents an oxygen atom, an NH group or an NH(C 1 -C 4 ) alkyl group, and Y represents a hydroxyl, amino, C 1 -C 4 alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino, or di(C 1 -C 4 ) alkylamino radical; or

in which:

Z 1 and Z 2 independently represent

a single covalent bond,

a divalent radical chosen from:

an —O(CH 2 ) p — radical, p denoting an integer ranging from 0 to 6,

an —NR' 6 (CH 2 ) q (C 6 H 4 ) t — radical, q denoting an integer ranging from 0 to 6 and t denoting 0 or 1. R′ 6 represents a hydrogen atom or a C 1 -C 6 alkyl radical optionally substituted with one or more hydroxyl groups,

Z 1 can also represent a divalent radical —S—, —SO— or —SO 2 — when R′ 1 , is a methyl radical,

R′ 1 , and R′ 2 represent independently:

a hydrogen,

a C 1 -C 10 alkyl radical, which is optionally substituted and optionally interrupted with a heteroatom or a group chosen from O, N, Si, S, SO and SO 2 ,

a halogen,

an SO 3 H radical,

a saturated, unsaturated or aromatic, substituted or unsubstituted, 5- to 8-membered ring optionally containing one or more heteroatoms or groups chosen from N, O, S, SO 2 and —CO—, it being possible for the ring to be cationic and/or substituted with a cationic radical,

an —N + R 17 R 18 R 19 group, R 17 , R 18 , and R 19 being linear or branched

C 1 -C 5 alkyls optionally substituted with one or more hydroxyl groups, when Z 1 or Z 2 represents a covalent bond, then R′ 1 , or R′ 2 can also represent one of the following radicals:

optionally substituted C 1 -C 6 alkylcarbonyl,

—O—CO—R, —CO—O—R, NR—CO—R′ or —CO—NRR′ in which R and R′ independently represent a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical,

R′ 3 , R′ 4 and R′ 5 , which may be identical or different, represent:

a hydrogen atom,

a hydroxyl radical,

a C 1 -C 6 alkoxy radical,

a C 1 -C 6 alkylthio radical,

an amino radical,

a monoalkylamino radical,

a C 1 -C 6 dialkylamino radical in which the alkyl radicals can form, with the nitrogen atom to which they are attached, a saturated or unsaturated and aromatic or non-aromatic 5- to 8-membered heterocycle which can contain one or more heteroatoms or groups chosen from N, O, S, SO 2 and CO, it being possible for the hetrocycle to be cationic and/or substituted with a cationic radical,

an optionally substituted C 1 -C 6 alkylcarbonyl radical,

an —O—CO—R, —CO—O—R, NR—CO—R′ or —CO—NRR′ radical with R and R′ as defined above,

a halogen,

an —NHSO 3 H radical,

an optionally substituted C 1 -C 4 alkyl radical,

a saturated, unsaturated or aromatic and optionally substituted carbon ring,

it being possible for R′ 3 , R′ 4 and R′ 5 to form, in pairs, a saturated or unsaturated ring,

X represents an ion or a group of ions which makes it possible to provide the electronegativity of the derivative of formula (II),

with the condition that at least one of the groups R′ 1 , and R′ 2 represents a cationic radical,

in which:

R 11 , R 12 , R 13 and R 14 , which may be identical or different, represent:

a linear or branched C 1 -C 6 alkyl radical optionally substituted with one or more radicals chosen from the group constituted of an OR 15 radical, an NR 6 R 7 radical, a carboxyl radical, a sulphonic radical, a carboxamido radical CONR 16 R 17 , a sulphonamido radical SO 2 NR 16 R 17 , a heteroaryl, an aryl optionally substituted with a (C 1 -C 4 ) alkyl group, a hydroxyl, a C 1 -C 2 alkoxy, an amino, a (di) (C 1 -C 2 ) alkylamino;

an aryl radical optionally substituted with one or more (C 1 -C 4 ) alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, (di) (C 1 -C 2 ) alkylamino;

a 5- or 6-membered heteroaryl radical optionally substituted with one or more radicals chosen from (C 1 -C 4 ) alkyl and (C 1 -C 2 ) alkoxy;

R 13 and R 14 can also represent a hydrogen atom;

R 15 , R 16 and R 17 , which may be identical or different, represent a hydrogen atom; a linear or branched C 1 -C 4 alkyl radical optionally substituted with one or more radicals chosen from the group constituted of a hydroxyl, a C 1 -C 2 alkoxy, a carboxamido CONR 18 R 19 , a sulphonyl SO 2 R 18 , an aryl optionally substituted with a (C 1 -C 4 ) alkyl, a hydroxyl, a C 1 -C 2 alkoxy, an amino, a (di) (C 1 -C 2 ) alkylamino; an aryl optionally substituted with a (C 1 -C 4 ) alkyl, a hydroxyl, a C 1 -C 2 alkoxy, an amino, a (di) (C 1 -C 2 ) alkylamino;

R 16 and R 17 , which may be identical or different, can also represent a carboxamido radical CONR 18 R 19 ; a sulphonyl SO 2 R 18 ;

R 18 and R 19 , which may be identical or different, represent a hydrogen atom; a linear or branched C 1 -C 4 alkyl radical optionally substituted with one or more hydroxyl or C 1 -C 2 alkoxy;

R 11 and R 12 , on the one hand, and R 13 and R 14 , on the other hand, can form, with the nitrogen atoms to which they are attached, a saturated or unsaturated heterocycle comprising 5 to 7 ring members, optionally substituted with one or more radicals chosen from the group constituted of halogen atoms, amino, (di) (C 1 -C 4 ) alkylamino, hydroxyl, carboxyl, carboxamido and (C 1 -C 2 ) alkoxy radicals, and C 1 -C 4 alkyl radicals optionally substituted with one or more hydroxyl, amino, (di) alkylamino, alkoxy, carboxyl, or sulphonyl radicals;

R 13 and R 14 can also form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, the carbon atoms of which can be replaced with an optionally substituted oxygen or nitrogen atom.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2012
From: COUROUX, ANNE-MARIE; FADLI, AZIZ
To: L'OREAL S.A.
Reel/Frame 028281/0380 →
Priority Claims (3)
FR 09 55637 · Aug 12, 2009 · national
FR 09 55638 · Aug 12, 2009 · national
FR 09 55640 · Aug 12, 2009 · national
Continuity (4)
Provisional Application 61234386 · Aug 17, 2009
Provisional Application 61234381 · Aug 17, 2009
Provisional Application 61235110 · Aug 19, 2009
Related Publication 20120278997A1 · Nov 8, 2012