# US 5,344,463 A · Hair dye compositions and methods utilizing 2-substituted-1-naphthol couplers

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- Number: US 5,344,463 A
- Document ID: US5344463A
- Status: Granted
- Kind: A
- Application number: 08/061,517
- Filed: 1993-05-17
- Granted: 1994-09-06
- Earliest claimed: 1993-05-17
- Assignees: Clairol Incorporated
- Inventors: Alexander Chan; Yuh-Guo Pan; Mu-Ill Lim; Richard Demarco
- Web page: https://patentgrep.com/patent/US5344463A

## CPC

- A61K 8/347: {Phenols}
- A61Q 5/10: Preparations for permanently dyeing the hair
- 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

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.

## Claims

### Claim 1

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.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, amino C.sub.1 -C.sub.6 alkyl wherein the amino group is substituted by R.sup.1 and R.sup.2, R.sup.1 and R.sup.2 being independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.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 (depends on 1)

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 3 (depends on 1)

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.sub.3 and R.sub.4 are, independently, hydrogen, C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, amino C.sub.1 -C.sub.6 alkyl, or acylamino C.sub.1 -C.sub.6 alkyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or halogen; R.sub.6 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; and n is 1 or when R.sub.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.sub.7 is hydrogen, C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 carboxyl, or halogen, and n is 1 or when R.sub.7 is methyl n is 1 or 2; and
(iii) 4-amino-1naphthol or 4-[(2-acetamidoethyl)amino]phenol, or (iv) mixtures thereof.

### Claim 4 (depends on 3)

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 5 (depends on 1)

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 6 (depends on 1)

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 7

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.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, amino C.sub.1 -C.sub.6 alkyl, wherein the amino group is substituted by R.sup.1 and R.sup.2, R.sup.1 and R.sup.2 being independently selected from the group consisting of hydrogen, hydroxy C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.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 8 (depends on 7)

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 9 (depends on 7)

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.sub.3 and R.sub.4 are, independently, hydrogen, C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, amino C.sub.1 -C.sub.6 alkyl, or acylamino C.sub.1 -C.sub.6 alkyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or halogen; R.sub.6 is hydrogen, halogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy and n is 1 or when R.sub.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.sub.7 is hydrogen, C.sub.1 -C.sub.6 alkyl, hydroxy C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 carbonyl, or halogen, and n is 1 or when R.sub.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 10 (depends on 9)

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 11 (depends on 7)

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 12 (depends on 7)

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 13 (depends on 5)

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 14 (depends on 11)

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.