# US 8,784,505 B2 · 1-hexzl-1H-pyrazole-4,5-diamine hemisulfate, and its use in dyeing compositions

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- Number: US 8,784,505 B2
- Document ID: US8784505B2
- Status: Granted
- Kind: B2
- Application number: 13/768,570
- Filed: 2013-02-15
- Published: 2013-08-22
- Granted: 2014-07-22
- Earliest claimed: 2012-02-16
- Assignees: The Procter & Gamble Company
- Applicants: The Procter & Gamble Company
- Inventors: Wolfram Geibel; Ingo Weber; Armin Osan; Markus Speckbacher
- Web page: https://patentgrep.com/patent/US8784505B2

## CPC

- A61K 8/494: {with more than one nitrogen as the only hetero atom}
- A61Q 5/10: Preparations for permanently dyeing the hair
- C07D 231/38: Nitrogen atoms (nitro radicals C07D231/16)
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

1-hexyl-1H-pyrazole-4,5-diamine hemisulfate, as represented in formula (IX-a), and its use in oxidative dyeing composition. This pyrazole salt was found to combine good stability as raw material and good shade intensity with a range of common couplers when formulated in hair dyeing composition.

## Claims

### Claim 1

A method for imparting improved color intensity as a result of dyeing human keratin fibers, the method comprising applying to human keratin fibers a composition comprising 1-hexyl-1H-pyrazole-4,5-diamine hemisulfate.

### Claim 2 (depends on 1)

The method of claim 1 wherein 1-hexyl-1H-pyrazole-4,5-diamine hemisulfate is a primary intermediate.

### Claim 3 (depends on 2)

The method of claim 2, wherein the composition further comprises one or more couplers selected from the group consisting of: resorcinol, 4-chlororesorcinol, 2-chlororesorcinol, 2-methylresorcinol, 4,6-dichlorobenzene-1,3-diol, 2,4-dimethylbenzene-1,3-diol, m-aminophenol, 4-amino-2-hydroxytoluene, 2-methyl-5-hydroxyethylaminophenol, 3-amino-2,6-dimethylphenol, 3-amino-2,4-dichlorophenol, 5-amino-6-chloro-o-cresol, 5-amino-4-chloro-o-cresol, 6-hydroxybenzomorpholine, 2-amino-5-phenylphenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 2-amino-5-ethoxyphenol, 5-methyl-2-(methylamino)phenol, 2,4-diaminophenoxyethanol, 2-amino-4-hydroxyethylaminoanisole, 1,3-bis-(2,4-diaminophenoxy)-propane, 2,2′-(2-methyl-1,3-phenylene)bis(azanediyl)diethanol, benzene-1,3-diamine, 2,2′-(4,6-diamino-1,3-phenylene)bis(oxy)diethanol, 3-(pyrrolidin-1-yl)aniline, 1-(3-(dimethylamino)phenyl)urea, 1-(3-aminophenyl)urea, 1-naphthol, 2-methyl-1-naphthol, 1,5-naphthalenediol, 2,7-naphthalenediol or 1-acetoxy-2-methylnaphthalene, 4-chloro-2-methylnaphthalen-1-ol, 4-methoxy-2-methylnaphthalen-1-ol, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dimethoxy-3,5-pyridinediamine, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine, 2,6-diaminopyridine, pyridine-2,6-diol, 5,6-dihydroxyindole, 6-hydroxyindole, 5,6-dihydroxyindoline, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, 1,2,4-trihydroxybenzene, 2-(benzo[d][1,3]dioxol-5-ylamino)ethanol (also known as hydroxyethyl-3,4-methylenedioxyaniline), physiologically compatible water-soluble salts thereof and mixtures thereof.

### Claim 4 (depends on 2)

The method of claim 2, wherein the composition further comprises one or more additional primary intermediates selected from the group consisting of: toluene-2,5-diamine, p-phenylenediamine, N-phenyl-p-phenylenediamine, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-hydroxyethyl-p-phenylenediamine, hydroxypropyl-bis-(N-hydroxyethyl-p-phenylenediamine), 2-methoxymethyl-p-phenylenediamine, 2-(1,2-dihydroxyethyl)-p-phenylenediamine, 2,2′-(2-(4-aminophenylamino)ethylazanediyl) diethanol, 2-(2,5-diamino-4-methoxyphenyl)propane-1,3-diol, 2-(7-amino-2H-benzo[b][1,4]oxazin-4(3H) -yl)ethanol, 2-chloro-p-phenylenediamine, p-aminophenol, p-(methylamino)phenol, 4-amino-m-cresol, 2-methoxy-p-phenylenediamine, 2,2′-methylenebis-4- aminophenol, 2,4,5,6-tetraminopyrimidine, 2,5,6-triamino-4-pyrimidinol, 1-hydroxyethyl-4,5-diaminopyrazole sulfate, 4,5-diamino-1-methylpyrazole, 4,5-diamino-1-ethylpyrazole, 4,5diamino-1-isopropylpyrazole, 4,5-diamino-1-butylpyrazole, 4,5-diamino-1-pentylpyrazole, 4,5-diamino-1-benzylpyrazole, 2,3-diamino-6,7-dihydropyrazolo[1,2-a]pyrazol-1(5H)-one dimethosulfonate, physiologically compatible water-soluble salts thereof, and mixtures thereof.