US4666453A
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Nitro-meta-phenylenediamines halogenated in the 6th position and their use in dyeing keratinic substances
Assignee: L'Oréal SA
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Filing: 1986-06-10
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Granted: 1987-05-19
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Expires: 2006-06-10
Abstract
Abstract The invention relates to compounds of formula <IMAGE> in which X denotes a halogen atom, and R and R' denote a hydrogen atom, an alkyl, polyhydroxyalkyl, hydroxyalkoxyalkyl or alkoxyalkyl radical or an aminoalkyl radical optionally substituted on the nitrogen atom provided that at least one of the groups R and R' is a polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical, and to dye compositions for keratinic fibres in which they are employed, to the preparation process and to intermediates.
Inventors
- 👤 Alex Junino
- 👤 Gerard Lang
- 👤 Ginette Jeanminet
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 00:25
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/418; A61Q; A61Q5/00; A61Q5/06; A61Q5/065; A61Q5/10; C; C07; C07C; C07C211/00; C07C211/43; C07C211/44; C07C211/52; C07C215/00; C07C215/02; C07C215/04; C07C215/06; C07C215/16; C07C217/00; C07C217/02; C07C217/04; C07C217/06; C07C217/08; C09; C09B; C09B51/00
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
55 words
Compound corresponding to the formula: ##STR20## in which x denotes a halogen atom, R and R' denote a hydrogen atom, an alkyl, polyhydroxyalkyl, hydroxyalkoxyalkyl or alkoxyalkyl radical or an aminoalkyl radical optionally substituted on the nitrogen atom provided that at least one of the groups R or R' is a polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical.
Claim 2
Dependent Claim
55 words
Compound corresponding to the formula: ##STR20## in which x denotes a halogen atom, R and R' denote a hydrogen atom, an alkyl, polyhydroxyalkyl, hydroxyalkoxyalkyl or alkoxyalkyl radical or an aminoalkyl radical optionally substituted on the nitrogen atom provided that at least one of the groups R or R' is a polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical.
Claim 3
Dependent Claim
14 words
Compound according to claim 1, corresponding to formula (I) in which X denotes chlorine.
Claim 4
Dependent Claim
42 words
Compound according to claim 1, wherein R' and/or R denote the group --CH 2 --CHOHCH 2 OH, --CH 2 --CH 2 --OCH 2 --CH 2 --OH, --CH 2 --CH 2 --O--CH 3 or --CH 2 --CH 2 --CH 2 --O--CH 3 .
Claim 5
Dependent Claim
17 words
Use of the compound as defined in claim 1 for dyeing keratinic fibres and especially human hair.
Claim 6
Dependent Claim
51 words
Dye composition for keratinic fibres and especially for human hair containing in a cosmetically acceptable solvent medium, a compound as defined in claim 1, in an amount effective for direct dyeing of the keratinic fibres or for imparting complementary highlights to the base colour in the case of an oxidation dyeing.
Claim 7
Dependent Claim
30 words
Composition according to claim 5, wherein the compound of formula (I) is present in proportions of between 0.001 and 5% by weight relative to the total weight of the composition.
Claim 8
Dependent Claim
30 words
Composition according to claim 5 containing additionally other direct dyes chosen from azo or anthraquinone dyes, or nitro dyes of the benzene series other than the compounds of formula (I).
Claim 9
Dependent Claim
68 words
Composition according to claim 7, wherein the nitro dyes of the benzene series other than the compounds of formula (I) are chosen from the blue or violet nitro dyes corresponding to the formula (IX): ##STR21## in which R 2 denotes a hydrogen atom, an alkyl, hydroxyalkyl, polyhydroxyalkyl or alkoxyalkyl radical, and R 3 and R 4 have the same meanings as R 2 and may not denote hydrogen.
Claim 10
Dependent Claim
45 words
Compositions according to claim 5 containing organic solvents chosen from benzyl or phenylethyl alcohols, lower alkanols, polyols, glycols or glycol ethers used by themselves or mixed and present in proportions of between 1 and 75% by weight relative to the total weight of the composition.
Claim 11
Dependent Claim
38 words
Composition according to claim 5 containing additionally anionic, cationic, nonionic or amphoteric surface-active agents or a mixture thereof, which are present in proportions of between 0.5 and 55% by weight relative to the total weight of the composition.
Claim 12
Dependent Claim
18 words
Composition according to claim 5 containing additionally thickeners present in proportions of between 0.1 and 10% by weight.
Claim 13
Dependent Claim
21 words
Composition according to claim 5 under the form of an aqueous, alcoholic or aqueous-alcoholic solution containing at least one cosmetic resin.
Claim 14
Dependent Claim
15 words
Dye composition according to claim 5 containing additionally one or more precursors of oxidation dyes.
Claim 15
Dependent Claim
44 words
Composition according to claim 13, wherein the precursors of oxidation dyes are p-phenylenediamines, para-aminophenols, heterocyclic pyridine or morpholine derivatives combined or not combined with couplers chosen from meta-diphenols, meta-aminophenols, meta-phenylenediamines, meta-acylaminophenols, meta-ureidophenols, meta-carbalkoxyaminophenols, α-naphthol, diketonic compounds, or pyrazolones and heterocyclic couplers derived from pyridine.
Claim 16
Dependent Claim
43 words
Composition according to claim 13 containing also reducing agents which are sodium sulphite, thioglycolic acid, thiolactic acid, sodium bisulphite, ascorbic acid and hydroquinone, which are present in proportions of between 0.05 and 1.5% by weight relative to the total weight of the composition.
Claim 17
Dependent Claim
32 words
Composition according to claim 13 wherein the precursors of oxidation dyes are present in proportions of between 0.001 and 5% by weight, the pH of the compositions being between 7 and 11.5.
Claim 18
Dependent Claim
36 words
Process for dyeing keratinic fibres, especially human hair, comprising the steps of applying a composition as defined in claim 5 to the said fibres for 5 to 40 minutes, and washing if appropriate, rinsing and drying.
Claim 19
Dependent Claim
51 words
Process for dyeing keratinic fibres, and especially human hair, wherein the composition according to claim 13 is applied to the said fibres, in an amount sufficient to develop the colour with the aid of an oxidizing agent present in the dye composition, or applied to the fibres in a second stage.
Claim 20
Dependent Claim
54 words
Process for the preparation of the compounds as defined in claim 1, wherein in an aliphatic amine of formula RNH 2 is reacted with a dihalogenated p-nitroaniline corresponding to the formula (II): ##STR22## in which R, R' and X have the same meanings as those indicated in any one of claims 1 to 3.
Claim 21
Dependent Claim
144 words
Process according to claim 19, wherein the compound of formula (II) is prepared by starting with the dihalogenated aniline converted to a monoarylsulphonamide by reaction with an arylsulphonyl chloride, followed by a nitration using concentrated nitric acid to obtain a compound of formula (V): ##STR23## which is then subjected to an acid hydrolysis to produce the compound of formula (II) in which R' denotes H, or that a halide of formula YR' in which Y denotes a halogen atom and R' has the meaning indicated in claim 1 is reacted with the compound of formula (V) in a solvent to produce a compound of formula (VI): ##STR24## which, by means of acid hydrolysis, produces the compound of formula (II) in which R' denotes an alkyl, polyhydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl radical or an aminoalkyl radical in which the nitrogen atom may be substituted if appropriate.
Claim 22
Dependent Claim
76 words
Process for the preparation of the compounds according to claim 1, wherein an aliphatic amine of formula R'NH 2 , in which R' has the meaning indicated in claim 1, is reacted with a dihalogenated ortho-nitroaniline of formula (VII): ##STR25## in which R and X have the same meanings as those indicated in any one of claims 1 to 3 at a temperature of between 20° C. and 180° C. in the presence of a solvent.
Claim 23
Dependent Claim
41 words
Process for the preparation of a compound defined in claim 1, in which R has the same meaning as R' other than hydrogen, wherein an amine RNH 2 is reacted with a 2,4,5-trihalonitrobenzene in the presence of a solvent if appropriate.
Claim 24
Dependent Claim
62 words
Compound corresponding to the formula (II): ##STR26## in which X denotes a halogen atom and R' denotes a (C 1 -C 6 )alkyl, polyhydroxy(C 2 -C 6 )alkyl, (C 1 -C 3 )alkoxy(C 1 -C 6 )alkyl or hydroxy(C 2 -C 6 )alkoxy(C 1 -C 4 )alkyl radical or an amino(C 1 -C 6 )alkyl radical optionally substituted on the nitrogen atom.
Claim 25
Dependent Claim
62 words
Compound corresponding to the formula (II): ##STR26## in which X denotes a halogen atom and R' denotes a (C 1 -C 6 )alkyl, polyhydroxy(C 2 -C 6 )alkyl, (C 1 -C 3 )alkoxy(C 1 -C 6 )alkyl or hydroxy(C 2 -C 6 )alkoxy(C 1 -C 4 )alkyl radical or an amino(C 1 -C 6 )alkyl radical optionally substituted on the nitrogen atom.
Claim 26
Dependent Claim
36 words
Compound corresponding to the formula (VII): ##STR27## in which X denotes halogen and R denotes a (C 1 -C 3 )alkoxy(C 1 -C 6 )alkyl or hydroxy(C 2 -C 4 )alkoxy(C 1 -C 4 )alkyl radical.
Claim 27
Dependent Claim
36 words
Compound corresponding to the formula (VII): ##STR27## in which X denotes halogen and R denotes a (C 1 -C 3 )alkoxy(C 1 -C 6 )alkyl or hydroxy(C 2 -C 4 )alkoxy(C 1 -C 4 )alkyl radical.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-05-18 | 1990-11-17 | 1991-05-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-18 | 1994-11-17 | 1995-05-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-18 | 1998-11-17 | 1999-05-19 | $7700.00 | Window Closed / Lapsed |