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WO2005023209A1 - Agent et procede pour colorer des fibres de keratine - Google Patents

Agent et procede pour colorer des fibres de keratine Download PDF

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Publication number
WO2005023209A1
WO2005023209A1 PCT/EP2004/002473 EP2004002473W WO2005023209A1 WO 2005023209 A1 WO2005023209 A1 WO 2005023209A1 EP 2004002473 W EP2004002473 W EP 2004002473W WO 2005023209 A1 WO2005023209 A1 WO 2005023209A1
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WO
WIPO (PCT)
Prior art keywords
group
diamino
branched
straight
chain
Prior art date
Application number
PCT/EP2004/002473
Other languages
German (de)
English (en)
Inventor
Martina Glattfelder
Iris Bahnmüller
Uwe Lenz
Original Assignee
Wella Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wella Aktiengesellschaft filed Critical Wella Aktiengesellschaft
Publication of WO2005023209A1 publication Critical patent/WO2005023209A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to an agent for coloring keratin fibers, in particular human hair, which is mixed with an oxidizing agent before use and contains at least one 4,5-diaminopyrazole derivative and at least one 1-naphthol derivative substituted in the 2-position ,
  • R1 is a straight-chain or branched (C1-C10) alkyl group, a straight-chain or branched (C1-C10) alkenyl group, a straight-chain or branched (C1-C10) interrupted by one to three heteroatoms or hetero groups (O, S, NH) ) Alkyl group, a straight-chain or branched (C2-C10) alkoxyalkyl group, a straight-chain or branched (C2-C10) aminoalkyl group, a straight-chain or branched di (C4-C12) alkylamino (C2-C6) alkyl group, a straight-chain or branched morpholino (C6-C14) alkyl group, a benzoaromatic of the formula (A) [where R 'and R "independently of one another are hydrogen, a straight-chain or branched (C1-C6) alkyl group, a hydroxyl group, a straight-chain or branched (C1
  • L is a benzyl group of the formula (B) [where R '"is hydrogen, a straight-chain or branched (C1-C6) alkyl group, a straight-chain or branched (C1-C6) alkoxy group or a halogen atom (for example F, Cl, Br)],
  • an optionally substituted pyridinyl group an optionally substituted pyrazinyl group, an optionally substituted pyrimidinyl group, an optionally substituted pyridazinyl group, an optionally substituted pyrrolyl group, an optionally substituted imidazolyl group, an optionally substituted pyrazolyl group, an optionally substituted furyl group, an optionally substituted thiophenyl group, an optionally substituted triazolyl group, an optionally substituted triazinyl group, an optionally substituted naphthyl group, an optionally substituted azanaphthyl group, an optionally substituted diaza-naphthyl group, an optionally substituted triazanaphthyl group, an optionally substituted tetra group represents an optionally substituted acridinyl group, an optionally substituted pyrazolo [3,4-b] pyridinyl group, an optionally substituted pyrazolo [
  • R3 represents hydrogen, a straight-chain or branched (C1-C4) alkyl group, a straight-chain or branched (C2-C4) hydroxyalkyl group, a straight-chain or branched (C3-C6) dihydroxyalkyl group or a benzyl group;
  • R4 is hydrogen, a straight chain or branched (C1-C6) alkyl group, a (C1-C4) hydroxyalkyl group, a (C1-C4) aminoalkyl group, a (C1-C8) alkylamino group, a di (C1-C8) - alkylamino group, a (C1-C4) alkylamino (C1-C4) alkyl group or a di (C1-C4) alkylamino (C1-C4) alkyl group, an aryl group or a heteroaryl group;
  • R5 and R6 independently of one another are hydrogen, a straight-chain or branched (C1-C6) alkyl group, an aryl group, a heteroaryl group, a carboxylic acid group, a carboxylic ester group, an unsubstituted or substituted carboxamide group, a hydroxy group or a (C1-C4) hydroxyalkyl group represent, or R4 and R5 together form an (optionally substituted) (C1-C6) alkylene group;
  • Z is a (C1-C10) alkyl diradical which is optionally interrupted by a hetero atom (for example a nitrogen, oxygen or sulfur atom), a - optionally one or two times benzo-condensed and / or with a hydroxyl group or ( C1-C6) -alkyl group substituted- aromatic or heteroaromatic diradical, or a diradical of the formula -Ar- (Alk) n -Ar-, where Ar is equal to one (optionally substituted) arylene radical or heteroarylene radical (in particular phenylene radical or pyridylene radical), Alk is a —CH 2 group and n is an integer from 0 to 6; and x and y are each independently 0 or 1; and
  • R is a straight-chain or branched (C1-C6) -alkyl group, a straight-chain or branched (C1-C6) -hydroxyalkyl group, a straight-chain or branched (C1-C6) -aminoalkyl group [wherein the amino group has one or two radicals from the Group consisting of hydrogen, a straight-chain or branched (C1-C6) -alkyl group or a straight-chain or branched (C1-C6) -hydroxyalkyl group may be substituted], an optionally substituted pyrrolidinyl group or piperidinyl group, a halogen atom (for example F, Cl, Br , J) represents an ethylene group, a propylene group or a butylene group; R7 is hydrogen or a (C1-C4) acyl group, especially an acetyl group; and
  • X is hydrogen, a (C1-C6) alkoxy group or a halogen atom (e.g. F, Cl, Br, J).
  • Particularly preferred derivatives of the general formula (I) are the following compounds or their physiologically tolerable salts: 4,5-diamino-1- (4'-methylbenzyl) pyrazole; 4,5-diamino-1- (2'-hydroxyethyl) -1 H-pyrazole; 4,5-diamino-1-benzyl-1 H-pyrazole; 4,5-diamino-1-ethyl-1H-pyrazole; 4,5-diamino-1-isopropyl-1H-pyrazole; 4,5-diamino-1- (4'-methoxybenzyl) -1 H-pyrazole; 4,5-diamino-1 H-pyrazole; 4,5-diamino-1- (3'-methoxybenzyl) -1 H-pyrazole, 4,5-diamino-1- (4'-chlorobenzyl) -1 H-pyrazole, 4,5-diamino-1- benzyl-1 H
  • Preferred derivatives of the general formula (II) are the following compounds or their physiologically tolerable salts: bis (4,5-diamino-pyrazol-1-yl) methane, 1,2-bis (4,5-diamino-pyrazole) -1 -yl) -ethane, 1,3-bis (4,5-diamino-pyrazol-1-yl) propane, 1,3-bis (4,5-diamino-3-phenyl-pyrazole-1 -yl) -propane, 2,3-bis- (4,5-diamino-pyrazol-1-yl) -propan-1-ol, N-benzyl-2,3-bis- (4,5-diamino-pyrazole -1-yl) propionamide, 1,3-bis (4,5-diamino-pyrazol-1-yl) cyclohexane, 1,4-bis (4,5-diamino-pyrazol-1-yl-methyl) ) -benz
  • the following compounds of the general formula (III) and their physiologically tolerable salts are preferred: 2-methyl-1-naphthol, 2-ethyl-1-naphthol, 2-propyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2 -Hydroxyethyl-1-naphthol and especially the acetic acid (2-methylnaphtalin-1-yl) ester.
  • the colorant according to the invention can round off the color result and produce special color effects, further oxidation dye precursors, for example derivatives of p-phenylene diamine such as 2- (2 ', 5'- Diaminophenyl) ethanol, resorcinol derivatives such as resorcinol, 2-methylresorcinol or 4-chlororesorcinol, amino and hydroxy derivatives of 1,3-benzodioxole, as well as substantive dyes, such as 2-amino-4,6-dinitrophenol, 2- Ethylamino-4,6-dinitrophenol, 2 - [(2'-hydroxyethyl) amino] -4,6-dinitrophenol, 2-amino-6-chloro-4-nitrophenol or 2-chloro-6-ethylamino-4-nitrophenol, be added.
  • p-phenylene diamine such as 2- (2 ', 5'- Diaminophenyl) ethanol
  • resorcinol derivatives such as res
  • the compounds of the formulas (I), (II) and (III) can, like the oxidative and direct dyes described above both in the form of the free base and in the form of their physiologically tolerable salts with inorganic or organic acids, such as, for example, hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, lactic acid or citric acid, in particular in the form of the hydrochlorides or sulfates.
  • inorganic or organic acids such as, for example, hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, lactic acid or citric acid, in particular in the form of the hydrochlorides or sulfates.
  • these compounds can also be present as alkali phenolates.
  • the total concentration of dye precursors in the colorant according to the invention is about 0.1 to 20 percent by weight, preferably 0.2 to 6 percent by weight.
  • concentration of the compounds of the formula (I), (II) and (III) and of the oxidation dye precursors and substantive dyes is in each case about 0.01 to 5 percent by weight, preferably 0.1 to 4 percent by weight.
  • antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite; Perfume oils; complexing; Wetting agents; emulsifiers; Thickener; Care substances and other auxiliaries and additives suitable for cosmetic products are included.
  • the preparation form for the colorant according to the invention can, for example, be a solution, in particular an aqueous or aqueous-alcoholic solution; a cream; be a gel or an emulsion.
  • Their composition represents a mixture of the dye components with the additives customary for such preparations.
  • Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, n-propanol and isopropanol or glycols such as glycerol and 1,2-propylene glycol, furthermore wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric or non-ionic surface-active substances such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanolamides, ethoxylated fatty alcohol alcohols, higher fatty alcohol alcohols, ethoxylated fatty alcohol alcohols, ethoxylated fatty alcohols,
  • the constituents mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight (based on the colorant), the thickeners in an amount of about 0.1 to 25 percent by weight ( based on the colorant) and the care substances in a concentration of about 0.1 to 5.0 percent by weight (based on the colorant).
  • the hair dye according to the invention is mixed with a liquid oxidizing agent in a suitable ratio.
  • the colorant and the oxidizing agent are preferably mixed with one another in a weight ratio of about 5: 1 to 1: 3, a weight ratio of 1: 1 to 1: 2 being particularly preferred.
  • the pH value of the ready-to-use hair dye according to the invention is adjusted to a pH value when the colorant composition, which is preferably alkaline, is mixed with the mostly acidic oxidizing agent, which is influenced by the amounts of alkali in the colorant and the amounts of acid in the oxidizing agent and by the mixing ratio.
  • the pH of the finished hair dye is about 3 to 11, preferably 5 to 9.
  • organic and inorganic acids such as phosphoric acid, ascorbic acid and lactic acid, or alkalis such as monoethanolamine, triethanolamine, 2-amino-
  • alkalis such as monoethanolamine, triethanolamine, 2-amino-
  • 2-methyl-1-propanol, ammonia, sodium hydroxide solution, potassium hydroxide solution or tris (hydroxymethyl) aminomethane can be used.
  • the colorant according to the invention described above is mixed with the oxidizing agent immediately before use and an amount sufficient for hair dyeing treatment is applied to the hair, generally about 60 to 200 grams of the ready-to-use oxidizing dye obtained, depending on the hair volume on.
  • the main oxidizing agents that can be used are hydrogen peroxide or its addition compounds with urea, melamine or sodium bromate in the form of a 1 to 12 percent, preferably ⁇ percent, aqueous solution, hydrogen peroxide being particularly preferred.
  • the colorant according to the invention is allowed to act on the hair at 15 to 50 degrees Celsius for about 10 to 45 minutes, preferably for 25 to 40 minutes (in particular 30 minutes), then the hair is rinsed with water and dried. If necessary, after this rinse, wash with a shampoo and possibly rinse with a weak organic acid, such as citric acid or tartaric acid. The hair is then dried.
  • the agents according to the invention enable bright red and violet shades that do not change even in sunlight and have particularly good wash resistance.
  • the agents according to the invention are very well suited for the so-called "air oxidation dyeing" and, even without the addition of chemical oxidizing agents (such as hydrogen peroxide), result in a comparison with those available on the market Products with significantly more intense coloring.
  • the pH value of the hair dye solution is 10.5.
  • 10 g of the hair dye solution described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water).
  • the ready-to-use oxidation dye with a pH value of 9.5 to 9.8 is applied to the hair.
  • the hair is rinsed with water, shampooed and dried. The hair gets an intense raspberry red color.
  • the pH value of the hair dye cream is 10.5.
  • 10 g of the hair dye cream described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water).
  • the ready-to-use oxidation dye with a pH of 9.5 to 9.8 thus obtained is applied to the hair and, after an exposure time of 30 minutes at 40 ° C., rinsed with water and dried.
  • the hair treated in this way has a bright raspberry red color.
  • the pH value of the hair dye gel is 10.5.
  • the pH value of the hair dye solution is 10.5.
  • Example 5 Oxidation hair dye, acidic 10.00 g isopropanol 10.00 g lauryl alcohol diglycol ether sulfate sodium salt, (28 percent aqueous solution) 10.00 g ammonia (25 percent aqueous solution) 0.30 g of ascorbic acid 1, 50 g of 4,5-diamino-1 - (4'-methylbenzyl) -1 H-pyrazole sulfate 1, 20 g of acetic acid (2-methylnaphtalin-1-yl) ester ad 100.00 g of water, fully desalinated
  • the pH value of the hair dye solution is 10.5.
  • 10 g of the hair dye solution described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water) and the ready-to-use oxidation dye so obtained is adjusted to a pH of 6.8 with phosphoric acid.
  • the oxidation coloring agent is then applied to the hair. After an exposure time of 30 minutes at 40 ° C, the hair is rinsed with water, shampooed and dried. The hair gets an intense raspberry red color.
  • the pH value of the hair dye cream is 10.5.
  • 10 g of the hair coloring cream described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water) and the ready-to-use oxidation coloring agent thus obtained is adjusted to a pH of 6.8 with phosphoric acid.
  • the oxidation coloring agent is then applied to the hair and, after an exposure time of 30 minutes at 40 ° C., rinsed with water and dried.
  • the hair treated in this way has a bright red color.
  • the pH value of the hair dye cream is 10.5.
  • the pH value of the hair dye cream is 10.5.
  • the pH value of the hair dye cream is 10.5.
  • the pH value of the hair dye cream is 10.5.
  • the pH value of the hair dye cream is 10.5.
  • 10 g of the hair coloring cream described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water) and the ready-to-use oxidation coloring agent thus obtained is adjusted to a pH of 6.8 with phosphoric acid.
  • the oxidation coloring agent is then applied to the hair and, after an exposure time of 30 minutes at 40 ° C., rinsed with water and dried.
  • the hair treated in this way has been given a pink color.
  • the pH value of the hair dye cream is 10.5.
  • the pH value of the hair dye cream is 10.5.
  • the pH value of the hair dye cream is 10.5.
  • 10 g of the hair coloring cream described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water) and the ready-to-use oxidation coloring agent thus obtained is adjusted to a pH of 6.8 with phosphoric acid.
  • the oxidation coloring agent is then applied to the hair and, after an exposure time of 30 minutes at 40 ° C., rinsed with water and dried.
  • the hair treated in this way has received a pink-violet color.
  • 70 g of the hair dye is allowed to act on human hair for 15 minutes. It is then rinsed with water and then dried.
  • 70 g of the hair dye is allowed to act on human hair for 15 minutes. It is then rinsed with water and then dried.
  • 70 g of the hair dye is allowed to act on human hair for 15 minutes. It is then rinsed with water and then dried.
  • 70 g of the hair dye is allowed to act on human hair for 15 minutes. It is then rinsed with water and then dried.
  • 10 g of the hair dye described above are mixed with 10 g of a hydrogen peroxide solution ( ⁇ percent solution in water) and the ready-to-use oxidation dye thus obtained is adjusted to a pH of 6.8 with phosphoric acid.
  • the oxidation coloring agent is then applied to the hair and, after an exposure time of 30 minutes at 40 ° C., rinsed with water and dried.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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Abstract

La présente invention concerne un agent pour colorer des fibres de kératine, qui contient une combinaison formée (a) de 4,5-diaminopyrazoles de formule (I) et/ou (II) et (b) de dérivés de 1-naphtol substitués en position 2 de formule (II). La présente invention concerne également des procédés pour colorer des cheveux en utilisant le colorant susmentionné.
PCT/EP2004/002473 2003-08-07 2004-03-11 Agent et procede pour colorer des fibres de keratine WO2005023209A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10336202.9 2003-08-07
DE2003136202 DE10336202A1 (de) 2003-08-07 2003-08-07 Mittel und Verfahren zur Färbung keratinischer Fasern

Publications (1)

Publication Number Publication Date
WO2005023209A1 true WO2005023209A1 (fr) 2005-03-17

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PCT/EP2004/002473 WO2005023209A1 (fr) 2003-08-07 2004-03-11 Agent et procede pour colorer des fibres de keratine

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DE (1) DE10336202A1 (fr)
WO (1) WO2005023209A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8444711B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzene-1,3-diamine and derivatives thereof
US8444714B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-Hexy1/Hepty1-4,5-diaminopyrazole and a benzene-1,3-diol and derivatives thereof
US8444712B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzo[1,3]dioxol-5-ylamine and derivatives thereof
US8444710B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a m-aminophenol and derivatives thereof
US8444709B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a 2-aminophenol and derivatives thereof
US8444713B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a naphthalen-1-ol and derivatives thereof
US8460397B2 (en) 2011-02-22 2013-06-11 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a pyridine and derivatives thereof
US8785656B2 (en) 2012-02-16 2014-07-22 The Procter & Gamble Company Telescoping synthesis of 5-amino-4-nitroso-1-alkyl-1H-pyrazole salt
US8784505B2 (en) 2012-02-16 2014-07-22 The Procter & Gamble Company 1-hexzl-1H-pyrazole-4,5-diamine hemisulfate, and its use in dyeing compositions
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

Families Citing this family (1)

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FR2974503B1 (fr) * 2011-04-29 2013-04-12 Oreal Composition de coloration mettant en oeuvre un coupleur 1-hydroxynaphtalenique et une base heterocyclique en milieu riche en corps gras, le procede de coloration et le dispositif

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EP0630642A1 (fr) * 1993-05-17 1994-12-28 Bristol-Myers Company Naphtol comme coupleurs
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EP0943316A2 (fr) * 1998-03-12 1999-09-22 Wella Aktiengesellschaft Agent pour colorer et decolorer des cheveux
US20010009044A1 (en) * 1996-10-18 2001-07-26 Hans-Juergen Braun Oxidative hair dye precursor compositions containing 4-5-diaminopyrazole, 5-amino-2-methylphenol and m-phenylenediamine compounds and method of dyeing hair

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EP0630642A1 (fr) * 1993-05-17 1994-12-28 Bristol-Myers Company Naphtol comme coupleurs
US20010009044A1 (en) * 1996-10-18 2001-07-26 Hans-Juergen Braun Oxidative hair dye precursor compositions containing 4-5-diaminopyrazole, 5-amino-2-methylphenol and m-phenylenediamine compounds and method of dyeing hair
US5849042A (en) * 1997-11-19 1998-12-15 Bristol-Myers Squibb Hair dye compositions containing 2,3 dialkyl-4-aminophenol and a 2-alkyl-1-naphthol
EP0943316A2 (fr) * 1998-03-12 1999-09-22 Wella Aktiengesellschaft Agent pour colorer et decolorer des cheveux

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JP2016074719A (ja) * 2011-02-22 2016-05-12 ザ プロクター アンド ギャンブル カンパニー １−ヘキシル／ヘプチル−４，５−ジアミノピラゾール及びナフタレン−１−オール及びこれらの誘導体を含む酸化染色組成物
US8444714B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-Hexy1/Hepty1-4,5-diaminopyrazole and a benzene-1,3-diol and derivatives thereof
US8444712B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzo[1,3]dioxol-5-ylamine and derivatives thereof
US8444710B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a m-aminophenol and derivatives thereof
US8444709B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a 2-aminophenol and derivatives thereof
US8444713B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a naphthalen-1-ol and derivatives thereof
US8460397B2 (en) 2011-02-22 2013-06-11 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a pyridine and derivatives thereof
JP2014510059A (ja) * 2011-02-22 2014-04-24 ザ プロクター アンド ギャンブル カンパニー １−ヘキシル／ヘプチル−４，５−ジアミノピラゾール及びナフタレン−１−オール及びこれらの誘導体を含む酸化染色組成物
US8444711B2 (en) 2011-02-22 2013-05-21 The Procter & Gamble Company Oxidative dyeing compositions comprising an 1-hexyl/heptyl-4,5-diaminopyrazole and a benzene-1,3-diamine and derivatives thereof
US8785656B2 (en) 2012-02-16 2014-07-22 The Procter & Gamble Company Telescoping synthesis of 5-amino-4-nitroso-1-alkyl-1H-pyrazole salt
US20140289973A1 (en) * 2012-02-16 2014-10-02 The Procter & Gamble Company 1-Hexyl-1H-Pyrazole-4,5-Diamine Hemisulfate, and Its Use in Dyeing Compositions
JP2015507014A (ja) * 2012-02-16 2015-03-05 ザ プロクター アンド ギャンブルカンパニー １−ヘキシル−１ｈ−ピラゾール−４，５−ジアミンヘミサルフェート及びその染色組成物中での使用
JP2015507013A (ja) * 2012-02-16 2015-03-05 ザ プロクター アンド ギャンブルカンパニー ５−アミノ−４−ニトロソ−１−アルキル−１ｈ−ピラゾール塩のテレスコーピング合成
US9060953B2 (en) 2012-02-16 2015-06-23 The Procter & Gamble Company 1-hexyl-1H-pyrazole-4,5-diamine hemisulfate, and its use in dyeing compositions
US8784505B2 (en) 2012-02-16 2014-07-22 The Procter & Gamble Company 1-hexzl-1H-pyrazole-4,5-diamine hemisulfate, and its use in dyeing compositions
JP2016153411A (ja) * 2012-02-16 2016-08-25 ザ プロクター アンド ギャンブル カンパニー ５−アミノ−４−ニトロソ−１−アルキル−１ｈ−ピラゾール塩のテレスコーピング合成
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof

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