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
  • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa

Definitions

• an aqueous composition for dyeing human hair comprising an oxidation dyestuffs combination of a Nov, l9, i974 developer component and a coupling component and customary oxidation dyestuff adjuvants, the improvement which comprises utilizing as said oxidation dyestuff combination, (a) from 0.3 to .5 percent by weight of said composition, of a coupling component 3- aminopyrazol-S-one having the formula Ill 1 0 wherein R is selected from the group consisting of NH--COR ---Nl-l CO--Nl-l-R and N- H-CS-NH-R wherein R is selected from the group consisting of a hydrocarbon radical with l to 12 carbon atoms and a heterocyclic radical, and (b) from 0.3 to 5 percent by weight of said composition, of a developer component compound, known for hair dyes, selected from the group consisting of aromatic polyfunctional amines
• An object of the present invention is, in an aqueous composition for dyeing human hair comprising an oxidation dyestuffs combination of a developer component and a coupling component and customary oxidation dyestuff adjuvants, the improvement which comprises utilizing as said oxidation dyestuff combination, (a) from 0.3 percent to 5 percent by weight of said composition, of a coupling component 3-aminopyrazol-S-one having the formula wherein R is selected from the group consisting of N- H-COR NH-CONHR and NHC- S--NH-R wherein R is selected from the group consisting of alkyl having one to six carbon atoms, phenyl, halophenyl, alkylphenyl having 7 to 12 carbon atoms, alkoxyphenyl having 7 to 12 carbon atoms, dialkylaminophenyl having one to four carbon atoms in the alkyls, cyclohexyl, alkylcyclohe
• R is selected from the group consisting of hydrogen, alkyl having 1 to 10 carbon atoms, phenyl, alkylphenyl having 7 to 10 carbon atoms, alkoxyphenyl having 1 to 10 carbon atoms, aminophenyl-hydroxyphenyl, carboxyphenylfcarbamoylphnyl, "suirafili'riy'r'ana" timinosuifonylphenyl, and (3) amino-pyridines having the formula wherein R is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms and phenyl.
• Another object of the present invention is in the process of dyeing human hair which comprises treating the hair at temperatures of from 10C to 40C with an aqueous composition for dyeing human hair comprising an oxidation deystuff combination of a developer component and a coupling component and customary dyestuff adjuvants, in the presence of an oxidizing agent, the improvement which comprises utilizing as said oxidation dyestuff combination, (a) from 0.3 percent to 5 percent by weight of said composition, of a coupling component 3-amino-pyrazol-5-one having the formula wherein R is selected from the group consisting of -N- HCOR NHCO--NHR, and -NH-C- SNH-R wherein R is selected from the group consisting of alkyl having one to six carbon atoms, phenyl, halophenyl, alkylphenyl having 7 to 12 carbon atoms, alkoxyphenyl having 7 to l2 carbon atoms, dialkylaminophenyl having one to
• NH NHR' and NR' R is selected from the group consisting of alkyl having one to four carbon atoms, hydroxyalkyl having one to four carbon atoms, phenyl and p-aminophenyl, and R is selected from the group consisting of hydrogen, alkyl having one to four carbon atoms, alkoxy having one to four carbon atoms, hydroxyl and amino, (2) 4-amino-pyrazolones having the formula N(Ra)2 wherein R is selected frorn the group consisting of hydrogen, alkyl having one to four carbon atoms and phenyl.
• the new method of dyeing human hair with solutions, emulsions or creams, which contain oxidation dyestuffs and other additives customary for hair dyes is characterized in that the hair is treated in the presence of an oxidizing agent and at temperatures from l0C to 40C with 3-aminopyrazol-5-ones (coupling components) of the general formula I wherein R represents --NHCO-R or -N- HCONH-R or -NH*-CSNH-R and R denotes a hydrocarbon radical with l to l2 carbon atoms or a heterocyclic radical, and of developer components, known for hair dyes, based on aromatic dior polyfunctional amines with at least one primary amino group as well as one additional functional group in para-position, or on heteroaromatic amino compounds.
• the hydrocarbon radical R can be present in the form of an aliphatic, aromatic or cyclo-aliphatic radical and also contain halogen atoms, particularly chlorine, or, in the case of cyclic compounds, alkylor alkoxy groups or dialkylamino groups with alkyl chains of one to four carbon atoms.
• Suitable heterocyclic radicals for R are the pyridyl and piperidyl radicals.
• R can be alkyl having one to six carbon atoms such as methyl, ethyl, isopropyl, n-propyl, n-butyl; phenyl; halophenyl such as pchlorophenyl; alkylphenyl having from 7 to 12 carbon atoms such as p-methylphenyl, p-ethylphenyl, opropylphenyl; alkoxyphenyl having from 7 to 12 carbon atoms such as o-methoxyphenyl, pisopropoxyphenyl; dialkylaminophenyl having one to four carbon atoms in the alkyl such as pdimethylaminophenyl; cyclohexyl; alkylcyclohexyl having from 7 to l2 carbon atoms such as methylcyclohexyl; pyridyl; and piperidyl.
• 3-aminopyrazol-5-ones of the general formula ll are used as the coupling component compound where R is alkyl having one to six carbon atoms.
• Suitable developer components are aromatic di-and polyfunctional amines with at least one primary amino groups as well as one additional functional group in the ortho or para, preferably the para position.
• these compounds are ortho or para aromatic diamines or hydroxyamines which can contain in addition other functional groups, such as -OH, NH NHR and -N(R')
• the preferred aromatic developer components of the aromatic amine type are aromatic amines having the formulae R3 R2 R --Nm and Q-Nm wherein R, and R are each, in general, hydrogen or an organic radical with l to 10 carbon atoms.
• the organic radical R of the 4-amino-pyrazolone can consist, for example, of an alkyl radical with l to l carbon atoms or of an aryl or heterocyclic radical.
• functional groups such as --OH, NH NHCH N(CH or halogen atoms, particularly chlorine, can be present.
• suitable organic radicals are the following groups: COOH, COOR', CONHR' and CON(R') where R is lower alkyl or hydroxyalkyl with one to four carbon atoms.
• the organic radical R of the 4-amino-pyrazolone may be an alkyl radical of l to carbon atoms or also an aryl or heterocyclic radical.
• E inctional groups may Preferably in the above formula Ill, R is selected from the group consisting of hydrogen, alkyl having I to l0 carbon atoms, phenyl, p-aminophenyl, phalophenyl, p-hydroxyphenyl, p-methylaminophenyl,
• R is selected from the group consisting of hydrogen, alkyl having 1 to 10 carbon atoms, phenyl, alkylphenyl having 7 to 10 carbon atoms, al koxyphenyl having 1 to 10 carbon atoms, aminophenyl, hydroxyphenyl, carboxyphenyl, carbamoylphenyl, sulfophenyl and aminosulfonylphenyl.
• Particularly suitable is lphenyl-3-carbamoyl-4-aminopyrazol-5onc.
• Suitable aminopyrdines which can be utilized as developer component compounds are the aminopyridines having the formula wherein R is selected from the group consisting of hyfurther also be present.
• hydrocarbon radicals with l to ID carbon atoms can be present which contain as functional groups OH, -NH COOH, -CONH SO H and'SO NH
• phenyl is utilized for R
• the latter can contain alkylor hydroxyalkyl groups with one to four carbon atoms or other substituents, such as NH --OH, -COOH, CONH Ol' "SO gNHg.
• the colors can be developed both by atmospheric oxygen and by chemical oxidants.
• hydrogen peroxide or its addition products like percarbamide, melamine perhydrate and sodium perborate are used.
• the dyeing of the hair is effected at temperatures of to 40C, preferably at room temperature.
• the dye treatment of the living human hair is preferably for a period of 10 minutes to 1 hour followed by a rinsing of the hair.
• the hair dyeing compositions may be applied in the form of aqueous solutions, but expecially in the form of creams or emulsions.
• the developer and coupling component compounds are mixed with any optional wetting agents or washing compositions, especially anionic or non-ionic substances.
• Suitable wetting and washing agents are especially alkylbenzenesulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, products of addition of ethylene oxide to higher alkyl amines and fatty alcohols, and fatty alcohol alkyl ether and polyalkyl ether sulfates.
• the absorptive capacity of the above-mentioned dyestuffs is also good when they are in admixture with such compositions. Consequently, the hair dyes can be produced in the form of shampoos, especially of cream shampoos, which are much desired in practice.
• thickeners such as, for example, methylcellulose, starch, higher fatty alcohols, vaselines, paraffin oil and fatty acids, and also perfume or hair conditioning substances such as, for example, pantothenic acid and cholesterol, may be admixed with the compositions of the invention.
• the added substances are used in the amount customary for these purposes. Suitable added amounts of wetting agents are, especially, 0.5 percent to 30 per cent by weight, and of thickeners, are 0.1 percent to 25 percent by weight, referred in each case to the total composition.
• concentration of the dyestuff components is to a certain extent dependent on the purpose of use and amounts, in each case, to 0.3 to 5 percent by weight, preferably 0.5 to 2.5 percent by weight. These quantities are also with reference to the total composition.
• the hair dyes are adjusted so that they are alkaline, preferably to a pH value of 8 to 10.
• the dyeings obtained with the hair dyes described above have good properties with respect to light, washing and rubbing.
• the dye cream so obtained dyed grey hair a yellowbrown when treated at room temperature over a period of 30 minutes. After the dye treatment, the hair was rinsed with water and shampooed.
• EXAMPLE 2 2 Parts by weight of p-(2,5-diaminopyridine)- dihydrochloride and 2 parts by weight of l-phenyl-3- (3'-ethylureido)-pyrazol-5-one were dissolved in water and worked into an emulsion as in Example 1. The mixture was adjusted to a pH of 9.5. 1 Part by weight of hydrogen peroxide was added and made up to 100 parts by weight with water.
• EXAMPLE 3 used as developer and coupling components. Under similar conditions with a period of action of 25 minutes at a temperature of about 30C, the dye colors indicated in the right column of the Table were obtained.
• the coupling components used correspond all to the general formula 1.
• CiHr-NHC-NH 4 El CiHr-NHC-NH 4 El
• a developer component compound selected from the group consisting of (1) an aromatic amine,
• said developer component compound is selected from the group consisting of l-phenyl-3-carbamoyl-4-amino-pyrazol- 5-one, p-toluylene-diamine, p-diaminoanisole, p-(N,N- dimethylamino)-aniline, p-aminodiphenylamine and 2,5-diaminopyridine.

Landscapes

• 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)

Applications Claiming Priority (1)

Publications (1)

Family

ID=5747147

Family Applications (1)

Country Status (12)

Cited By (3)

Families Citing this family (1)

Citations (6)

• 0
  • BE BE756849D patent/BE756849A/xx unknown
• 1969
  • 1969-10-02 DE DE19691949748 patent/DE1949748A1/de active Pending
• 1970
  • 1970-09-07 NL NL7013198A patent/NL7013198A/xx unknown
  • 1970-09-07 SE SE7012119A patent/SE375447B/xx unknown
  • 1970-09-07 DK DK458770AA patent/DK126969B/da unknown
  • 1970-09-24 US US00075304A patent/US3849064A/en not_active Expired - Lifetime
  • 1970-09-24 CA CA093,972A patent/CA939270A/en not_active Expired
  • 1970-09-29 FR FR7035097A patent/FR2064098B1/fr not_active Expired
  • 1970-10-01 AT AT887370A patent/AT301760B/de not_active IP Right Cessation
  • 1970-10-01 CH CH1453270A patent/CH530791A/de not_active IP Right Cessation
  • 1970-10-01 ZA ZA706682A patent/ZA706682B/xx unknown
  • 1970-10-01 GB GB4665670A patent/GB1312109A/en not_active Expired

Patent Citations (6)

Also Published As

Similar Documents