US3617167A - Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair - Google Patents

Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair Download PDF

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Publication number
US3617167A
US3617167A US568750A US3617167DA US3617167A US 3617167 A US3617167 A US 3617167A US 568750 A US568750 A US 568750A US 3617167D A US3617167D A US 3617167DA US 3617167 A US3617167 A US 3617167A
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US
United States
Prior art keywords
hair
dyeing
percent
dyestuff
human hair
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
US568750A
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English (en)
Inventor
Peter Berth
Karl-Josef Boosen
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Therachemie Chemische Therapeutische GmbH
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Therachemie Chemische Therapeutische GmbH
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Priority claimed from CH725366A external-priority patent/CH489246A/de
Application filed by Therachemie Chemische Therapeutische GmbH filed Critical Therachemie Chemische Therapeutische GmbH
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Publication of US3617167A publication Critical patent/US3617167A/en
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Classifications

    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom

Definitions

  • an aqueous composition for dyeing human hair comprising an oxidation dyestuff and customary dyestuff adjuvants in the presence of an oxidizing agent, and thereafter 4 rinsing the hair
  • R is a member selected from the group consisting of [56] Cm hydrogen, coma. coon, -COOR', alkyl having 1 to 10 UNITED STATES PATENTS carbon atoms, phenyl and nicotinoyl; R represents an alkyl 2,9 /l K lOPiS i a l- 3/l0.2 having 1 to 4 carbon atoms consisting of hydrogen. alkyl hav- 3,01 1,858 l2/l96l Lantz et al. 8/l0.2 ing 1 to 10 carbon atoms, phenyl and p-sulfonamidophenyl; .12 .2 2 4/1 4 wilmsm nn et l.-
  • R and R individually may be hydrogen or an organic radical having no more than ten carbon atoms or coupling components known per se for dyes.
  • the organic radical R of the 4-aminopyrazolone may be an alkyl having one-l C-atoms or an aryl or a heterocyclic radical.
  • functional groups may be present, such as -OH, -NH NHCH -N(Cl-l;,) or halogen, especially chlorine.
  • the following groups should be named: -COOH, -COOR, -CONHR', CONRR", wherein R and R" are an alkyl or hydroxyalkyl having one to four carbon atoms.
  • the organic radical R in the above formula may be an alkyl having one to carbon atoms or an aryl or a heterocyclic radical, Functional groups may be present therein. Particularly to be named are hydrocarbon radicals having one to 10 C-atoms containing as functional groups -OH, -NH -COOH, CONH -SO H and -SO,NH
  • aromatic radical is phenyl.
  • the same may contain alkyl or hydroxyalkyl groups having one to four carbon atoms or other substituents, such as NH OH, COOH, CONH SO H and SO NH Pyrazolones substituted with a radical R as named are produced by the reaction of beta-ketoacidesters with correspondingly substituted hydrazines, followed by nitrozation and reduction to the amino-compounds.
  • Suitable coupling components are known for hair dyeing agents. Suitable are amines, diamines, phenols, napthols, polyphenols and aminophenols. When using diamines, aminophenols and phenols, the orthoor meta-compounds are preferred. The following compounds are especially suited:
  • Coloring oftli hair with these agents cfii be az'cam nshed, as with other oxidizing dyes, by means of atmospheric oxygen or with chemical oxidizers, preferably hydrogen peroxide or its additives, especially on urea, melamine and sodium borate.
  • the hair is dyed at temperatures ranging from 15 to 40 C preferably at room temperature.
  • the dyeing agents can be applied in aqueous solution but preferably as emulsion or as a cream or paste.
  • the 4-aminopyrazolones and the coupling components can be admixed to any desired wetting agents or detergents, especially anionic or nonionic ones.
  • suitable detergents or wetting agents are alkylbenzenesulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamines, ethylene additives on fatty acids or fatty alcohols.
  • the coloring properties of the dyes on the human hair are good also in mixture with the agents named.
  • the hair dyeing agents can be produced in the form of shampoos, especially cream shampoos, which frequently is desirable in practice.
  • the agents may contain thickeners, e.g. methylcellulose, starch, higher fatty alcohols, petrolatum (Vaseline), paraffin oil and fatty acids; also perfumes, i.e., essential oils; or hair treating agents such as pantothenic acid and cholesterol.
  • thickeners e.g. methylcellulose, starch, higher fatty alcohols, petrolatum (Vaseline), paraffin oil and fatty acids; also perfumes, i.e., essential oils; or hair treating agents such as pantothenic acid and cholesterol.
  • additives named are applied in the quantities customary for these purposes.
  • Detergents or wetting agents preferably are employed in amounts of -b 0.5-30 weight percent, thickeners in amounts of 0. l-25 percent, all calculated on the total composition.
  • concentration of the dyes, also calculated on the total composition is up to 5 percent, and preferably 0.l to 2 percent by weight.
  • the hair dyeing agents can be applied in weakly acid, neutral or especially in alkaline pH range.
  • the coloration of the hair thus attained has good light-, washand abrasion-resistance (rub-resistance) and can readily be removed again with reducing agents, e.g., sodium hydroxymethanesulfinate. This contrasts from the commonly known hair dyeing agents which greatly resist their removal, once applied to the hair.
  • Parts named in the examples are parts by weight; temperatures are degrees centigrade.
  • EXAMPLE I A solution was prepared from 2 parts 3-methyl-4-aminopyrazolone hydrochloride, 1 part resorcinol and 0.5 parts sodium sulfite in parts water. The pH was adjusted to 9.5 with ammonia, and the solution made up to 100 parts with water. Shortly before application, 4 parts H 0, (30 percent) were admixed thereto. This mixture was allowed to act on naturally grey living human hair at room temperature. After 20 minutes, the hair was rinsed and thoroughly shampooed. A strong red color was obtained. When, in lieu of the resorcinol, 1 part m-toluylenediamine was used, the hair assumed a redviolet color.
  • EXAMPLE 2 A solution was prepared as described in the preceding example except that 3 parts 4-aminopyrazolone-3-carboxylic acid amide hydrochloride were used instead of 3-methyl-4- aminopyrazolone. Under the conditions of example 1, a strong red color was obtained.
  • EXAMPLE 3 A solution consisting of 1.5 parts 4-aminopyrazolone hydrochloride, l part m-diaminoanisol, 1 part sodium sulfite, 5 parts of a thickener consisting of celluloseglycolate, in parts water was adjusted to a pH or nine with ammonia and made up to parts with water. The paste thus obtained dyed gray hair, after mixing with 8 parts melamine perhydrate, to a red-violet color within 30 minutes at room temperature.
  • EXAMPLE 4 A paste was prepared as described in example 3, except that, instead of the 4-aminopyrazolone, parts 3-phenyl-4- aminopyr-azolone were used, and the pH was held at 8. Living grey hair attained a red-violet color under the same conditions as given above.
  • EXAMPLE 5 An emulsion was prepared from parts fatty alcohol (C -C 10 parts fatty alcohol sulfate, 2 parts of the hydrochloride of 4-aminopyrazolone-3-carboxylic acid ethylester, 1 part alpha-naphthol and 77 parts water. The emulsion had a pH of 3.0 and was mixed with 10 parts sodiumperborate. This cream was applied to grey hair for minutes at C. and imparted thereto a deep blue color. This color could be completely removed again by a 20 minute treatment with a 3 percent aqueous Rongalit C solution (trade mark for sodium hydroxymethanesulfinate).
  • EXAMPLE 6 A cream was prepared as described in example 5, except that the alpha-naphthol used therein was replaced by 1 part of one of the coupling components listed in table 1. The color obtained under like conditions as in example 5, also is listed in table 1.
  • oxidation dyestuff utilizin as said oxidation dyestuff, from 0.1 percent to 5 percent y weight, based on the total aqueous composition, of an oxidation dyestuff combination of (a) a developer component compound having the formula wherein R is a member selected from the group consisting of hydrogen, -COOH, COOR', alkyl having one to 10 carbon atoms, and phenyl; R represents an alkyl having one to four carbon atoms, and R is a member selected from the group consisting of hydrogen, alkyl having one to 10 carbon atoms, phenyl and p-sulfonamidophenyl; and (b) a coupling component compound selected from the group consisting of oand m-phenylenediamine, oand m-amino-phenyl, oand mtoluylenediamine, o-anisidine, 2,4-diaminoanisol, 2,4- diaminophenyl

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
US568750A 1965-08-05 1966-07-29 Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair Expired - Lifetime US3617167A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DET0029157 1965-08-05
CH725366A CH489246A (de) 1965-08-05 1966-05-18 Haarfärbemittel

Publications (1)

Publication Number Publication Date
US3617167A true US3617167A (en) 1971-11-02

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US568750A Expired - Lifetime US3617167A (en) 1965-08-05 1966-07-29 Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair

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US (1) US3617167A (enrdf_load_stackoverflow)
AT (1) AT272526B (enrdf_load_stackoverflow)
BE (1) BE688594A (enrdf_load_stackoverflow)
DE (2) DE1492198C3 (enrdf_load_stackoverflow)
DK (1) DK113867B (enrdf_load_stackoverflow)
FR (1) FR1488169A (enrdf_load_stackoverflow)
GB (1) GB1146061A (enrdf_load_stackoverflow)
IT (1) IT942002B (enrdf_load_stackoverflow)
NL (1) NL6609633A (enrdf_load_stackoverflow)
SE (1) SE342141B (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3849064A (en) * 1969-10-02 1974-11-19 Therachemie Chem Therapeut Method and compositions for the dyeing of human hair
US3907494A (en) * 1971-10-04 1975-09-23 Therachemie Chem Therapeut Hair dyes based on diamino-nitro-benzene compounds
US4737458A (en) * 1984-06-19 1988-04-12 Boehringer Mannheim Gmbh Aminopyrazolinones, reagent containing them and the use thereof in the enzymatic determinaton of hydrogen peroxide
US6080332A (en) * 1995-06-05 2000-06-27 C.I.R.S. S.P.A. Procedure for the anti-scaler production for coating the polymerizing reactor and respective resultant product
EP1086685A1 (de) * 1999-09-24 2001-03-28 GOLDWELL GmbH Zwei-komponenten-kit eine lösung und eine Emulsion enthaltend und verfahren zum entfärben von gefärbten Haaren
US6464732B2 (en) 1997-05-13 2002-10-15 L'oreal S.A. Composition for dyeing keratin fibres, comprising a pyrazolin-4,5-dione and an aromatic primary amine
US6503282B1 (en) * 2000-01-07 2003-01-07 Wella Aktiengesellschaft Means and method for dying keratinic fibers
US20090044348A1 (en) * 2007-06-22 2009-02-19 Aziz Fadli Coloring composition comprising at least one azomethine compound with a pyrazolinone unit

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10148848A1 (de) * 2001-10-04 2003-04-17 Henkel Kgaa Verfahren zum Färben und späterem Entfärben von Haaren

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944869A (en) * 1957-01-21 1960-07-12 Oreal Process for dyeing keratinous material with ortho-diphenols
US3011858A (en) * 1958-04-15 1961-12-05 Oreal Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes
US3128232A (en) * 1959-03-21 1964-04-07 Wella Ag Oxidation dyestuff agent for human hair
US3200040A (en) * 1961-03-22 1965-08-10 Hans Schwarzkopf Hair dye comprising diaminopyridines
US3253980A (en) * 1959-08-08 1966-05-31 Therachemie Chem Therapeut Aminotriazine perhydrates oxidative hair compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944869A (en) * 1957-01-21 1960-07-12 Oreal Process for dyeing keratinous material with ortho-diphenols
US3011858A (en) * 1958-04-15 1961-12-05 Oreal Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes
US3128232A (en) * 1959-03-21 1964-04-07 Wella Ag Oxidation dyestuff agent for human hair
US3253980A (en) * 1959-08-08 1966-05-31 Therachemie Chem Therapeut Aminotriazine perhydrates oxidative hair compositions
US3200040A (en) * 1961-03-22 1965-08-10 Hans Schwarzkopf Hair dye comprising diaminopyridines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Harry, The Principles and Practice of Modern Cosmetics, p. 443, 1962. *
Vanieek et al., Collection of Czechoslovak Chemical Communications, Vol. 27, pp.2796 2800, (1962). *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3849064A (en) * 1969-10-02 1974-11-19 Therachemie Chem Therapeut Method and compositions for the dyeing of human hair
US3907494A (en) * 1971-10-04 1975-09-23 Therachemie Chem Therapeut Hair dyes based on diamino-nitro-benzene compounds
US4737458A (en) * 1984-06-19 1988-04-12 Boehringer Mannheim Gmbh Aminopyrazolinones, reagent containing them and the use thereof in the enzymatic determinaton of hydrogen peroxide
US6080332A (en) * 1995-06-05 2000-06-27 C.I.R.S. S.P.A. Procedure for the anti-scaler production for coating the polymerizing reactor and respective resultant product
US6464732B2 (en) 1997-05-13 2002-10-15 L'oreal S.A. Composition for dyeing keratin fibres, comprising a pyrazolin-4,5-dione and an aromatic primary amine
US6679923B2 (en) 1997-05-13 2004-01-20 L'oreal S.A. Composition for dyeing keratin fibers, comprising a pyrazoline-4,5-dione and an aromatic primary amine
EP1086685A1 (de) * 1999-09-24 2001-03-28 GOLDWELL GmbH Zwei-komponenten-kit eine lösung und eine Emulsion enthaltend und verfahren zum entfärben von gefärbten Haaren
US6379657B1 (en) 1999-09-24 2002-04-30 Goldwell Gmbh Composition and process for de-coloring dyed hair
US6503282B1 (en) * 2000-01-07 2003-01-07 Wella Aktiengesellschaft Means and method for dying keratinic fibers
US20090044348A1 (en) * 2007-06-22 2009-02-19 Aziz Fadli Coloring composition comprising at least one azomethine compound with a pyrazolinone unit
US7582123B2 (en) 2007-06-22 2009-09-01 L'oreal S.A. Coloring composition comprising at least one azomethine compound with a pyrazolinone unit

Also Published As

Publication number Publication date
DE1492198B2 (de) 1974-02-21
IT942002B (it) 1973-03-20
DE1617876A1 (de) 1971-06-03
BE688594A (enrdf_load_stackoverflow) 1967-03-31
NL6609633A (enrdf_load_stackoverflow) 1967-02-06
AT272526B (de) 1969-07-10
FR1488169A (fr) 1967-07-07
GB1146061A (en) 1969-03-19
SE342141B (enrdf_load_stackoverflow) 1972-01-31
DE1492198A1 (de) 1969-12-04
DE1492198C3 (de) 1974-10-17
DK113867B (da) 1969-05-05
DE1617876C3 (de) 1975-06-19
DE1617876B2 (de) 1974-08-08

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