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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• Life Sciences & Earth Sciences (AREA)
• Health & Medical 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)

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Publications (1)

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Country Status (10)

Cited By (8)

Families Citing this family (1)

Citations (5)

• 1965
  • 1965-08-05 DE DE1492198A patent/DE1492198C3/de not_active Expired
• 1966
  • 1966-07-08 NL NL6609633A patent/NL6609633A/xx unknown
  • 1966-07-29 US US568750A patent/US3617167A/en not_active Expired - Lifetime
  • 1966-08-02 FR FR71724A patent/FR1488169A/fr not_active Expired
  • 1966-08-02 IT IT17954/66A patent/IT942002B/it active
  • 1966-08-03 AT AT745366A patent/AT272526B/de active
  • 1966-08-04 DK DK404566AA patent/DK113867B/da unknown
  • 1966-08-04 GB GB34906/66A patent/GB1146061A/en not_active Expired
  • 1966-08-05 SE SE10654/66A patent/SE342141B/xx unknown
  • 1966-09-08 DE DE1617876A patent/DE1617876C3/de not_active Expired
  • 1966-10-20 BE BE688594D patent/BE688594A/xx unknown

Patent Citations (5)

Non-Patent Citations (2)

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