US5984975A
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3-substituted para-aminophenols and use thereof in dyeing keratinous fibers
Assignee: L'Oréal SA
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Filing: 1997-06-04
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Granted: 1999-11-16
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Expires: 2017-06-04
Abstract
Abstract A method or composition for dyeing keratinous fibres using as an oxidation dye precursor a 3-substituted para-aminophenol of formula: ##STR1## where R 1 represents alkyl, alkenyl, mono- or polyhydroxyalkyl, cyano, cyanoalkyl, halogenoalkyl, aminoalkyl or alkoxyalkyl and R 2 represents hydrogen, alkyl or mono- or polyhydroxyalkyl, provided that when R 2 is hydrogen R 1 is not methyl or trifluoromethyl, and addition salts thereof with an acid.
Inventors
- 👤 Alain Lagrange
- 👤 Jean Jacques Vandenbosche
- 👤 Jean Cotteret
- 👤 Marie Pascale Audousset
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:03
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/41; A61K8/415; A23; A23L; A23L15/00; A23L5/00; A23L5/20; A23L5/23; A61Q; A61Q5/00; A61Q5/10; C; C07; C07C; C07C215/00; C07C215/74; C07C215/76; C07C215/78; C07C217/00; C07C217/76; C07C255/00; C07C255/01; C07C255/32; C07C255/42; C07C255/43; A23V; A23V2002/00; A23V2200/00; A23V2200/30; A23V2200/3262; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/54
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
196 words
Dye composition for keratinous fibres, comprising, in an aqueous dye medium, an amount effective for oxidation dyeing said fibres of at least one 3-substituted para-aminophenol as an oxidation dye precursor, said compound having the formula: ##STR19## wherein R 1 represents a C 1 -C 4 alkyl radical, a C 2 -C 4 alkenyl radical, a C 1 -C 6 monohydroxyalkyl, a C 2 -C 6 polyhydroxyalkyl radical, a C 2 -C 6 alkoxyalkyl radical, a C 1 -C 4 cyanoalkyl radical, a C 1 -C 4 halogenoalkyl radical, an aminoalkyl radical having the formula: ##STR20## where: n is a whole number from 1 to 6 inclusive; R 3 and R 4 , which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical, a C 1 -C 4 hydroxyalkyl radical or a C 1 -C 6 acyl radical; R 2 represents a hydrogen atom, a C 1 -C 6 alkyl radical, a C 1 -C 6 monohydroxyalkyl radical or a C 2 -C 6 polyhydroxyalkyl radical, provided that: when R 2 is hydrogen, R 1 does not represent methyl or trifluoromethyl, or an addition salt thereof with an acid.
Claim 2
Dependent Claim
196 words
Dye composition for keratinous fibres, comprising, in an aqueous dye medium, an amount effective for oxidation dyeing said fibres of at least one 3-substituted para-aminophenol as an oxidation dye precursor, said compound having the formula: ##STR19## wherein R 1 represents a C 1 -C 4 alkyl radical, a C 2 -C 4 alkenyl radical, a C 1 -C 6 monohydroxyalkyl, a C 2 -C 6 polyhydroxyalkyl radical, a C 2 -C 6 alkoxyalkyl radical, a C 1 -C 4 cyanoalkyl radical, a C 1 -C 4 halogenoalkyl radical, an aminoalkyl radical having the formula: ##STR20## where: n is a whole number from 1 to 6 inclusive; R 3 and R 4 , which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical, a C 1 -C 4 hydroxyalkyl radical or a C 1 -C 6 acyl radical; R 2 represents a hydrogen atom, a C 1 -C 6 alkyl radical, a C 1 -C 6 monohydroxyalkyl radical or a C 2 -C 6 polyhydroxyalkyl radical, provided that: when R 2 is hydrogen, R 1 does not represent methyl or trifluoromethyl, or an addition salt thereof with an acid.
Claim 3
Dependent Claim
27 words
Dye composition according to claim 1, wherein the 3-substituted para-aminophenol is 3-ethyl p-aminophenol, 3-hydroxymethyl p-aminophenol, 3-cyanomethyl p-aminophenol, 3-tert-butyl p-aminophenol, 3-(β-methoxyethyl) p-aminophenol, 3-(β-ethoxyethyl) p-aminophenol or a salt thereof.
Claim 4
Dependent Claim
34 words
Dye composition according to claim 1, wherein the composition further contains an effective amount of one or more couplers which are metadiphenols, metaaminophenols, metaphenylenediamines, metaacylaminophenols, metaureidophenols, metacarbalkoxyaminophenols, α-naphthol, indole derivatives, β-ketone compounds or pyrazoles.
Claim 5
Dependent Claim
49 words
Dye composition according to claim 1, wherein the composition further contains an effective amount of at least one para or ortho oxidation dye precursor which is a paraphenylenediamine, a para-aminophenol other than those with formula (I), a para heterocyclic derivative of pyridine or pyrimidine, an orthoaminophenol or a bis-phenylalkylenediamine.
Claim 6
Dependent Claim
52 words
Dye composition according to claim 1, wherein the composition contains 3-ethyl p-aminophenol or a salt thereof as an oxidation dye precursor, at least one coupler which is 2-methyl 5-aminophenol or 2-methyl 5-N-(β-hydroxyethyl) aminophenol or a salt thereof and at least one metaphenylenediamine or a salt thereof to act as an additional coupler.
Claim 7
Dependent Claim
60 words
Dye composition according to claim 1, wherein the composition contains 3-ethyl p-aminophenol or a salt thereof as an oxidation dye precursor, at least one coupler which is 2-methyl 5-aminophenol or 2-methyl 5-N-(β-hydroxyethyl) aminophenol or a salt thereof and an additional oxidation dye precursor which is an orthoaminophenol, a paraphenylenediamine, a bis-phenylalkylenediamine or a para-aminophenol other than those with formula (I).
Claim 8
Dependent Claim
29 words
Dye composition according to claim 1, wherein the composition contains 0.05% to 3.5% by weight with respect to the total composition weight of the at least one 3-substituted para-aminophenol.
Claim 9
Dependent Claim
34 words
Dye composition according to claim 1, wherein the composition contains a total of 0.3% to 7% by weight with respect to the total composition weight of ortho and para oxidation dye precursors and couplers.
Claim 10
Dependent Claim
98 words
Dye composition according to claim 1, wherein the composition further contains at least one additive which is an anionic, cationic, nonionic or amphoteric surfactant or a mixture thereof, in proportions of between 0.5% and 55% by weight, an organic solvent in concentrations of between 1% and 40% by weight, a thickening agent in proportions of between 0.1% and 5% by weight, an antioxidising agent in proportions of between 0.05% and 1.5% by weight, a direct dye, a penetrating agent, a sequestrating agent, a perfume or buffer, the percentages by weight being with respect to the total composition weight.
Claim 11
Dependent Claim
29 words
Dye composition according to claim 1, wherein the composition is in the form of a liquid, cream, gel or mousse and has a pH of between 4 and 11.
Claim 12
Independent Claim
216 words
A method of oxidation dyeing keratinous fibres, comprising applying to the fibres an effective amount for dyeing said fibres of at least one 3-substituted p-aminophenol as an oxidation dye precursor, said compound having the formula: ##STR21## wherein R 1 represents a C 1 -C 4 alkyl radical, a C 2 -C 4 alkenyl radical, a C 1 -C 6 monohydroxyalkyl, a C 2 -C 6 polyhydroxyalkyl radical, a C 2 -C 6 alkoxyalkyl radical, a C 1 -C 4 cyanoalkyl radical, a C 1 -C 4 halogenoalkyl radical, an aminoalkyl radical having the formula: ##STR22## where: n is a whole number from 1 to 6 inclusive; R 3 and R 4 , which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical, a C 1 -C 4 hydroxyalkyl radical or a C 1 -C 6 acyl radical; R 2 represents a hydrogen atom, a C 1 -C 6 alkyl radical, a C 1 -C 6 monohydroxyalkyl radical or a C 2 -C 6 polyhydroxyalkyl radical, provided that: when R 2 is hydrogen, R 1 does not represent methyl or trifluoromethyl, or an addition salt thereof with an acid, optionally in the presence of one or more couplers, wherein a color is developed by application of an oxidising agent.
Claim 13
Independent Claim
216 words
A method of oxidation dyeing keratinous fibres, comprising applying to the fibres an effective amount for dyeing said fibres of at least one 3-substituted p-aminophenol as an oxidation dye precursor, said compound having the formula: ##STR21## wherein R 1 represents a C 1 -C 4 alkyl radical, a C 2 -C 4 alkenyl radical, a C 1 -C 6 monohydroxyalkyl, a C 2 -C 6 polyhydroxyalkyl radical, a C 2 -C 6 alkoxyalkyl radical, a C 1 -C 4 cyanoalkyl radical, a C 1 -C 4 halogenoalkyl radical, an aminoalkyl radical having the formula: ##STR22## where: n is a whole number from 1 to 6 inclusive; R 3 and R 4 , which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical, a C 1 -C 4 hydroxyalkyl radical or a C 1 -C 6 acyl radical; R 2 represents a hydrogen atom, a C 1 -C 6 alkyl radical, a C 1 -C 6 monohydroxyalkyl radical or a C 2 -C 6 polyhydroxyalkyl radical, provided that: when R 2 is hydrogen, R 1 does not represent methyl or trifluoromethyl, or an addition salt thereof with an acid, optionally in the presence of one or more couplers, wherein a color is developed by application of an oxidising agent.
Claim 14
Dependent Claim
22 words
Method according to claim 11, wherein the 3-substituted para-aminophenol is 3-ethyl p-aminophenol, 3-hydroxymethyl p-aminophenol, 3-cyanomethyl p-aminophenol, 3-tert-butyl p-aminophenol, 3-(β-methoxyethyl)p-aminophenol or 3-(β-ethoxyethyl) p-aminophenol.
Claim 15
Dependent Claim
33 words
Method according to claim 11, wherein the 3-substituted para-aminophenol with formula (I) according to claim one or more couplers are metadiphenols, metaaminophenols, metaphenylenediamines, metaacyl-aminophenols, metaureidophenols, metacarbalkoxyaminophenols, α-naphthol, indole derivatives, β-ketone compounds or pyrazoles.
Claim 16
Dependent Claim
88 words
Method according to claim 11, wherein a dye composition containing the at least one 3-substituted para-aminophenol and optionally at least one coupler in an aqueous dye medium is mixed just before application with a sufficient quantity of oxidising solution to develop a color, the pH of the resulting composition varying from 3 to 11, and the mixture thus produced is applied to the keratinous fibres, left on said fibers for 10 to 40 minutes and then rinsed out, after which said fibres are shampooed, rinsed again and dried.
Claim 17
Dependent Claim
108 words
Method according to claim 11, wherein the at least one 3-substituted para-aminophenol is applied in a first step to the keratinous fibres, and in a second step a dye composition containing at least one coupler or at least one other oxidation dye precursor other than that with formula (I) is applied to the keratinous fibres, color is developed with an oxidising agent present in the composition applied in the second step, or applied to the keratinous fibres in a third step, the resulting composition is left on said fibers for 10 to 40 minutes and then rinsed out, after which the fibres are shampooed, rinsed again and dried.
Claim 18
Dependent Claim
45 words
3-Substituted para-aminophenol with formula: ##STR23## where R' 1 represents a cyano radical; R' 2 represents a C 1 -C 6 alkyl radical, a C 1 -C 6 monohydroxyalkyl radical or a C 2 -C 6 polyhydroxyalkyl radical; or an addition salt thereof with an acid.
Claim 19
Dependent Claim
45 words
3-Substituted para-aminophenol with formula: ##STR23## where R' 1 represents a cyano radical; R' 2 represents a C 1 -C 6 alkyl radical, a C 1 -C 6 monohydroxyalkyl radical or a C 2 -C 6 polyhydroxyalkyl radical; or an addition salt thereof with an acid.
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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) | 2002-11-15 | 2003-05-17 | 2003-11-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2006-11-15 | 2007-05-17 | 2007-11-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2010-11-15 | 2011-05-17 | 2011-11-16 | $7700.00 | Window Closed / Lapsed |