# US 7,744,658 B2 · Indole-derived styryl dye comprising an alkylene linker, a dye composition comprising this dye, and a process for lightening keratin materials using this dye

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- Number: US 7,744,658 B2
- Document ID: US7744658B2
- Status: Granted
- Kind: B2
- Application number: 12/234,072
- Filed: 2008-09-19
- Published: 2009-04-09
- Granted: 2010-06-29
- Earliest claimed: 2007-09-21
- Assignees: L'oreal
- Inventors: Andrew Greaves; Nicolas Daubresse
- Web page: https://patentgrep.com/patent/US7744658B2

## CPC

- C09B 23/04: one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
- A61K 8/4913: {having five membered rings, e.g. pyrrolidone carboxylic acid}
- A61K 8/492: {having condensed rings, e.g. indol}
- A61K 8/4926: {having six membered rings}
- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61K 8/4953: {containing pyrimidine ring derivatives, e.g. minoxidil}
- A61Q 5/065: {Preparations for temporary colouring the hair, e.g. direct dyes}
- C09B 23/0091: {having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol (styryl dyes see C09B23/14)}
- A61K 2800/434: Luminescent, Fluorescent; Optical brighteners; Photosensitizers
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

The disclosure relates to the dyeing of keratin materials using indole-derived styryl dyes comprising an alkylene linker. Disclosed herein is a dye composition comprising an indole-derived styryl dye comprising an alkylene linker, and a dyeing process with, for example, a lightening effect on keratin materials such as hair, using said composition. Disclosed herein are novel indole-derived styryl dyes comprising an alkylene linker and the uses thereof in lightening keratin materials. This composition makes it possible to obtain a coloring with a lightening effect which can be resistant and visible on dark keratin fibers.

## Claims

### Claim 1

A fluorescent dye of formula (I):
the organic or mineral acid salts thereof, optical isomers and geometric isomers thereof, or the solvates thereof:
wherein:
n is an integer ranging from 1 to 2;
m is an integer ranging from 0 to 1;
p is an integer ranging from 0 to 4;
Q− is an anionic counterion;
W is chosen from a (C2-C3)alkylene and a (C2-C3)alkenylene chain optionally substituted with at least one (C1-C4)alkyl or aryl group;
Z1 is chosen from a carbon atom and a nitrogen atom N+ which is quaternized;
Z2, Z3, and Z4, which may be identical or different, are chosen from a nitrogen atom, a CR4 group, and a N+R5 group; with the proviso that only one quaternized nitrogen atom N+ or N+R5 is present in the aromatic ring A;
R1, R2, and R4, which may be identical or different, are chosen from a hydrogen atom, a halogen atom, a (di)(C1-C6)(alkyl)amino, a cyano, a hydroxyl, a (poly)halo(C1-C6)alkyl, an acyl(C1-C4)(alkyl)amino, a (C1-C6)alkoxy, a (C1-C6)alkylthio, a (poly)hydroxy(C2-C6)alkoxy, a (C1-C6)alkylcarbonyloxy, a (C1-C6)alkoxycarbonyl, a (C1-C6)alkylcarbonylamino, a (di)(C1-C4)(alkyl)aminocarbonyl, a (C1-C6)alkylsulfonyl(C1-C4)(alkyl)amino, a (di)(C1-C4)(alkyl)aminosulfonyl group, and a (C1-C6)alkyl group optionally substituted with a group chosen from (C1-C6)alkoxy, hydroxyl, and (di)(C1-C6)(alkyl)amino; or, when p is an integer greater than or equal to 2, two contiguous radicals R2 form, together with the carbon atoms to which they are attached, a benzo ring;
R3 is chosen from a hydrogen atom, an optionally substituted (C1-C6)alkyl group, a (di)(C1-C6)(alkyl)amino group, an aryl group, and a heterocycloalkyl group which is optionally substituted;
R5 is chosen from an optionally substituted (C1-C6)alkyl group and an aryl(C1-C6)alkyl;
L is chosen from a σ bond and an optionally substituted C1-C20 divalent hydrocarbon-based chain, optionally interrupted i) with at least one divalent group or combination thereof chosen from: —N(R)—, —N+(R)(Ro)—, An−, —O—, —C(O)—, and —S(O)2—, wherein R and Ro, which may be identical or different, are chosen from a hydrogen, a (C1-C4)alkyl, a hydroxy(C1-C4)alkyl, and an amino(C1-C4)alkyl radical, and An− is an anionic counterion, or ii) with a cationic heterocycle or cationic heteroaryl Het+, An−, wherein An− is an anionic counterion and Het+ is chosen from a saturated or unsaturated heterocycle comprising from 5 to 10 members and a heteroaryl comprising from 5 to 10 members;
with the proviso that, when n is 2, then m is 0, and when n is 1, then m is 1.

### Claim 2 (depends on 1)

The fluorescent dye according to claim 1, wherein m and n are 1.

### Claim 3 (depends on 1)

The fluorescent dye according to claim 1, wherein n=2 and m=0.

### Claim 4 (depends on 1)

The fluorescent dye according to claim 1, wherein unit A:
a) Z1 is a quaternized nitrogen atom N+, and Z2, Z3, and Z4 are CR4, or Z3 and Z4 are CH and Z2 is chosen from a (C1-C6)alkylcarbonylamino and a (di)(C1-C4)(alkyl)-aminocarbonyl group;
b) Z2 is a group N+R5, Z1 is a carbon atom, and Z3 and Z4 are CR4;
c) Z4 is a group N+R5, Z1 is a carbon atom, and Z3 and Z2 are CR4; or
d) Z1 is a quaternized nitrogen atom N+, Z2 and Z4 are CR4, and Z3 is a nitrogen atom.

### Claim 5 (depends on 1)

The fluorescent dye according to claim 1, wherein the dye is of formula (Ia) below:
wherein:
n, m, and Q− are as defined in claim 1;
wherein unit A:
a) Z1 is a quaternized nitrogen atom N+, and Z2, Z3, and Z4 are CR4, or Z3 and Z4 are CH and Z2 is chosen from a (C1-C6)alkylcarbonylamino and a (di)(C1-C4)(alkyl)-aminocarbonyl group;
b) Z2 is a group N+R5, Z1 is a carbon atom, and Z3 and Z4 are CR4;
c) Z4 is a group N+R5, Z1 is a carbon atom, and Z3 and Z2 are CR4; or
d) Z1 is a quaternized nitrogen atom N+, Z2 and Z4 are CR4, and Z3 is a nitrogen atom;
q is an integer ranging from 1 to 2;
R1 is chosen from a hydrogen atom and a (C1-C6)alkyl group;
R2 is absent or is chosen from a halogen atom, a (C1-C3)alkoxy, and a (C1-C3)alkoxycarbonyl group;
R3 is chosen from a hydrogen atom, a (C1-C6)alkyl group, a phenyl group, a (di)(C1-C6)(alkyl)amino group, and a monocyclic, 5- to 7-membered heterocycloalkyl group comprising from 1 to 3 heteroatoms chosen from oxygen and nitrogen, optionally substituted with a (C1-C2)alkyl group;
R5 is chosen from an optionally substituted (C1-C6)alkyl group and an aryl(C1-C6)alkyl;
L′ is chosen from a σ bond, a (C2-C6)alkylene chain, and an optionally substituted (C1-C6)alkyl group;
with the proviso that, when n is 2, then m is 0, and when n is 1, then m is 1.

### Claim 6 (depends on 1)

The fluorescent dye according to claim 1, wherein the dye is chosen from one of the following formulae:
wherein An−, which may be identical or different, is an anionic counterion.

### Claim 7 (depends on 1)

A dye composition comprising, in a cosmetically acceptable medium, at least one fluorescent dye of formula (I) according to claim 1.

### Claim 8 (depends on 7)

The dye composition according to claim 7, wherein the at least one fluorescent dye of formula (I) is present in an amount ranging from 0.001% to 50% by weight relative to the total weight of the composition.

### Claim 9 (depends on 1)

A process for dyeing keratin materials, comprising applying to the keratin materials a cosmetic dye composition comprising at least one fluorescent dye of formula (I) according to claim 1.

### Claim 10 (depends on 9)

The process according to claim 9, wherein the keratin materials are dark keratin fibers.

### Claim 11 (depends on 9)

The process according to claim 9, wherein the keratin materials are dark keratin fibers having a tone height of less than or equal to 6.

### Claim 12 (depends on 9)

The process according to claim 9, wherein the keratin materials are lightened.