US5344463A
Expired / Lapsed
US
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Hair dye compositions and methods utilizing 2-substituted-1-naphthol couplers
Assignee: P&G Hair Care Holding Inc
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Filing: 1993-05-17
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Granted: 1994-09-06
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Expires: 2013-05-17
Abstract
Abstract 2-substituted-1-naphthols when coupled with an oxidation dye precursor in an oxidative dye system produce a long lasting intense color to hair. Use of such couplers makes available to the colorist novel oxidation hair dyes which surprisingly show a color shift to the red. Dyestuffs prepared through use of the 2-substituted-1-naphthol couplers are substantially more acid-fast compared to like dyestuffs using a 1-naphthol coupler. Compositions and a method of dyeing hair are also disclosed.
Inventors
- 👤 Alexander Chan
- 👤 Yuh-Guo Pan
- 👤 Mu-Ill Lim
- 👤 Richard DeMarco
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 21:02
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/34; A61K8/347; A61Q; A61Q5/00; A61Q5/10
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
198 words
In an oxidative dye composition for dyeing a keratin fiber, the composition containing an oxidation dye precursor, a coupler, at least one material selected from the group consisting of perfumes, antioxidants, sequestering agents, alkalizing agents, acidifying agents and developers and a cosmetically acceptable vehicle, the precursor and the coupler being present in respective amounts such that when the precursor is activated it reacts with the coupler to produce a tinctorially effective amount of a dye compound, the improvement which comprises the coupler is a 2-substituted-1-naphthol compound having the formula I ##STR4## or a salt thereof, wherein R is C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, amino C 1 -C 6 alkyl wherein the amino group is substituted by R 1 and R 2 , R 1 and R 2 being independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, or R 1 and R 2 taken together with the nitrogen atom to which they are attached forming a 5 or 6 membered saturated ring, or an olefinic group selected from the group consisting of ethylene, propylene and butylene, and X is hydrogen or halogen.
Claim 2
Dependent Claim
198 words
In an oxidative dye composition for dyeing a keratin fiber, the composition containing an oxidation dye precursor, a coupler, at least one material selected from the group consisting of perfumes, antioxidants, sequestering agents, alkalizing agents, acidifying agents and developers and a cosmetically acceptable vehicle, the precursor and the coupler being present in respective amounts such that when the precursor is activated it reacts with the coupler to produce a tinctorially effective amount of a dye compound, the improvement which comprises the coupler is a 2-substituted-1-naphthol compound having the formula I ##STR4## or a salt thereof, wherein R is C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, amino C 1 -C 6 alkyl wherein the amino group is substituted by R 1 and R 2 , R 1 and R 2 being independently selected from the group consisting of hydrogen, C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, or R 1 and R 2 taken together with the nitrogen atom to which they are attached forming a 5 or 6 membered saturated ring, or an olefinic group selected from the group consisting of ethylene, propylene and butylene, and X is hydrogen or halogen.
Claim 3
Dependent Claim
36 words
The composition according to claim 1, wherein the oxidation dye precursor is a primary intermediate and the compound of formula I is selected from the group consisting of 2-methyl-1-naphthol, 2-ethyl-1-naphthol, 2-propyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, and salts thereof.
Claim 4
Dependent Claim
174 words
The composition according to claim 1, wherein the oxidation dye precursor is a primary intermediate selected from the group consisting of (i) p-phenylenediamines having the formula II ##STR5## wherein R 3 and R 4 are, independently, hydrogen, C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, amino C 1 -C 6 alkyl, or acylamino C 1 -C 6 alkyl; R 5 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen; R 6 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy; and n is 1 or when R 6 is methyl n is 1 or 2 and acid addition salts thereof; (ii) p-aminophenols of the formula III ##STR6## or a salt thereof, wherein R 7 is hydrogen, C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 carboxyl, or halogen, and n is 1 or when R 7 is methyl n is 1 or 2; and (iii) 4-amino-1naphthol or 4-[(2-acetamidoethyl)amino]phenol, or (iv) mixtures thereof.
Claim 5
Dependent Claim
32 words
The composition according to claim 3, wherein the oxidation dye precursor is p-phenylenediamine, 2,6-dimethyl-3-methoxy-p-phenylenediamine dihydrochloride, 3-methoxy-4-amino-N,N-dimethylaniline sulfate or N,N-bis (2-hydroxyethyl)-p-phenylenediamine sulfate, p-aminophenol, 4-amino-2,6-dimethylphenol, 5-aminosalicylic acid, 4-[(2-acetamidoethyl)amino]phenol sulfate, 4-amino-2-methylphenol, 4-amino-3-methylphenol hydrochloride or 2,5-dimethyl-4-aminophenol.
Claim 6
Dependent Claim
22 words
The composition according to claim 1, wherein the oxidation dye precursor is p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, p-aminophenol, p-amino-m-methylphenol, p-amino-o-methylphenol, 5-aminosalicylic acid, 2,5-diaminotoluene or 4-amino-1-naphthol.
Claim 7
Dependent Claim
19 words
The composition according to claim 1, wherein the oxidation dye precursor is p-phenylenediamine, p-toluenediamine, p-aminophenol, 4-amino-2-methylphenol or N,N-bis(2-hydroxyethyl)-p-phenylenediamine sulfate.
Claim 8
Dependent Claim
173 words
In a method for dyeing hair including the steps of activating an oxidation dye precursor, reacting the activated oxidation dye precursor with a coupler to produce a tinctorially effective amount of a hair dye and applying the hair dye to a hair fiber; the improvement which comprises the coupler is a 2-substituted-1-naphthol compound having the formula I ##STR7## or a salt thereof, wherein R is C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, amino C 1 -C 6 alkyl, wherein the amino group is substituted by R 1 and R 2 , R 1 and R 2 being independently selected from the group consisting of hydrogen, hydroxy C 1 -C 6 alkyl, or R 1 and R 2 taken together with the nitrogen atom to which they are attached forming a 5 or 6 membered saturated ring, or an olefinic group selected from the group consisting of ethylene, propylene and butylene, and X is hydrogen or halogen, whereby said hair fiber is imparted a coloration having increased resistance to shampooing.
Claim 9
Dependent Claim
173 words
In a method for dyeing hair including the steps of activating an oxidation dye precursor, reacting the activated oxidation dye precursor with a coupler to produce a tinctorially effective amount of a hair dye and applying the hair dye to a hair fiber; the improvement which comprises the coupler is a 2-substituted-1-naphthol compound having the formula I ##STR7## or a salt thereof, wherein R is C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, amino C 1 -C 6 alkyl, wherein the amino group is substituted by R 1 and R 2 , R 1 and R 2 being independently selected from the group consisting of hydrogen, hydroxy C 1 -C 6 alkyl, or R 1 and R 2 taken together with the nitrogen atom to which they are attached forming a 5 or 6 membered saturated ring, or an olefinic group selected from the group consisting of ethylene, propylene and butylene, and X is hydrogen or halogen, whereby said hair fiber is imparted a coloration having increased resistance to shampooing.
Claim 10
Dependent Claim
36 words
The method, according to claim 7, wherein the oxidation dye precursor is a primary intermediate and the compound of formula I is selected from the group consisting of 2-methyl-1-naphthol, 2-ethyl-1-naphthol, 2-propyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1naphthol, and salts thereof.
Claim 11
Dependent Claim
174 words
The method, according to claim 7, wherein the oxidation dye precursor is a primary intermediate selected from the group consisting of (i) p-phenylenediamines having the formula II ##STR8## wherein R 3 and R 4 are, independently, hydrogen, C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, amino C 1 -C 6 alkyl, or acylamino C 1 -C 6 alkyl; R 5 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or halogen; R 6 is hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy and n is 1 or when R 6 is methyl n is 1 or 2; and acid addition salts thereof; (ii) p-aminophenols of the formula III ##STR9## or a salt thereof, wherein R 7 is hydrogen, C 1 -C 6 alkyl, hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 carbonyl, or halogen, and n is 1 or when R 7 is methyl n is 1 or 2; and (iii) 4-amino-1-naphthol or 4-[(2-acetamidoethyl)amino]phenol; and (iv) mixtures thereof.
Claim 12
Dependent Claim
31 words
The method according to claim 9, wherein the oxidation precursor is p-phenylenediamine, 2,6-dimethyl-3-methoxy-p-phenylenediamine dihydrochloride, 3-methoxy-4-amino-N,N-dimethylaniline sulfate or N,N-bis (2-hydroxyethyl)-p-phenylenediamine sulfate, p-aminophenol, 4-amino-2, 6-dimethylphenol, 5-aminosalicylic acid, 4[(2-acetamidoethyl)amino]phenol sulfate, 4-amino-2-methylphenol, 4-amino-3-methylphenolhydrochloride or 2,5-dimethyl-4-aminophenol.
Claim 13
Dependent Claim
22 words
The method according to claim 7, wherein the oxidation dye precursor is p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, p-aminophenol, p-amino-m-methylphenol, p-amino-o-methylphenol, 5-aminosalicylic acid, 2,5-diaminotoluene, or 4-amino-1-naphthol.
Claim 14
Dependent Claim
19 words
The method according to claim 7, wherein the oxidation dye precursor is p-phenylenediamine, p-toluenediamine, p-amino-phenol, 4-amino-2methylphenol or N,N-bis(2-hydroxyethyl)-p-phenylenediamine sulfate.
Claim 15
Dependent Claim
22 words
The composition according to claim 5, wherein the oxidation dye precursor is p-amino-o-methyl phenol and the coupler of formula I is 2-methyl-1-naphthol.
Claim 16
Dependent Claim
22 words
The method according to claim 11, wherein the oxidation dye precursor is p-amino-o-methyl phenol and the coupler of formula I is 2-methyl-1-naphthol.
References Cited (Backward Citations)
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