# US 5,710,311 A · 2-sulphured metaphenylenediamines for dyeing hair

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- Number: US 5,710,311 A
- Document ID: US5710311A
- Status: Granted
- Kind: A
- Application number: 08/536,369
- Filed: 1995-09-29
- Granted: 1998-01-20
- Earliest claimed: 1992-03-25
- Assignees: L'oreal
- Inventors: Alex Junino; Alain Genet; Alain Lagrange
- Web page: https://patentgrep.com/patent/US5710311A

## CPC

- A61K 8/46: containing sulfur (A61K8/44 takes precedence)
- A61Q 5/10: Preparations for permanently dyeing the hair
- C07C 323/36: the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
- C07C 323/41: Y being a hydrogen or an acyclic carbon atom
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

At least one 2-sulphured metaphenylenediamine of formula (I) ##STR1## used for dyeing keratin fibres, wherein Z is alkyl, aralkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or aminoalkyl; R.sub.1 and R.sub.2, which are the same or different, are hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, monocarbamylalkyl, dialkylcarbamyl, aminoalkyl, acyl carbalkoxy, carbamyl, or monoalkylcarbamyl; R.sub.3 is hydrogen, alkyl, nitrile, amide, fluoroalkyl, or --COOR; and the corresponding acid salts. A method for dyeing keratin fibres, and novel 2-sulphured metaphenylenediamines, are also disclosed.

## Claims

### Claim 1

A 2-sulfurated metaphenylenediamine having the formula ##STR19## wherein Z' represents C.sub.1 -C.sub.18 alkyl, aralkyl wherein the alkyl moiety is C.sub.1 -C.sub.6, C.sub.1 -C.sub.6 monohydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, aryl, aminoalkyl having the formula ##STR20## wherein n is an integer from 1 to 6;
R'.sub.4 and R'.sub.5, each independently, represent hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl or C.sub.1 -C.sub.6 acyl;
R'.sub.1 and R'.sub.2, each independently, represent hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 monohydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, C.sub.1 -C.sub.6 monocarbamoylalkyl, C.sub.1 -C.sub.6 dialkylcarbamoyl, C.sub.1 -C.sub.6 aminoalkyl, C.sub.1 -C.sub.6 acyl, C.sub.2 -C.sub.6 carbalkoxy, carbamyl or C.sub.1 -C.sub.6 monoalkylcarbamoyl;
R'.sub.3 represents hydrogen, C.sub.1 -C.sub.4 alkyl, nitrile, amide, C.sub.1 -C.sub.4 fluoroalkyl or --COOR wherein R represents hydrogen or C.sub.1 -C.sub.4 alkyl; and the acid salt thereof, with the proviso that:
(a) when R'.sub.1, R'.sub.2 and R'.sub.3 represent hydrogen, Z' is other than said C.sub.1 -C.sub.18 alkyl or said aryl;
(b) when Z' represents methyl and R'.sub.3 represents hydrogen, R'.sub.1 and R'.sub.2 do not represent the same C.sub.1 -C.sub.6 acyl,
(c) when Z' represents methyl and when R'.sub.3 represents hydrogen and when one of R'.sub.1 and R'.sub.2 represents hydrogen, the other R'.sub.1 and R'.sub.2 do not represent a C.sub.4 acyl;
(d) when R'.sub.1 and R'.sub.2 represent hydrogen and R'.sub.3 represents a trifluoromethyl in the 5 position, Z' does not represent C.sub.1 -C.sub.4 alkyl; and
(e) when R'.sub.1 and R'.sub.2 represent hydrogen and R'.sub.3 represents methyl in the 4 position, Z' does not represent methyl.

### Claim 2

A 2-sulfurated metaphenylenediamine selected from the group consisting of
2-(.beta.-acetylaminoethylthio)-1,3-diaminobenzene,
2-methylthio-5-methyl-1,3-diaminobenzene,
2-methylthio-5-amido-1,3-diaminobenzene and
2-methylthio-5-nitrilo-1,3-diaminobenzene.