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
• • 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
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
  • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
• • 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
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
• • 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

Definitions

• the novel means for dyeing human hair according to the invention are based on oxidation dyes and comprise [54] DYES heterocyclic amino compounds and suitable coupling com- COMPOUNDS ponents.
• 2 parts of G-aminotetrahydroquinoline 5 Claims No Draw 5 hydrochloride, 1 part of a-naphthol, 1 part of hydrogen peroxg ide are mixed with 96 parts of water and adjusted to a pH of [52] US. Cl 8/11, 9.5.
• By treating gray human hair with the resulting solution a l 8/ 10.2 dark blue coloration is obtained.
• the hair dyes according to the invention have, in addition to D06p 1/32 other favorable characteristics, the advantage of being easily [50] Field of Search 8/102, 11, removable from the hair, e.g., by reducing agents.
• This invention relates to'agentsfor dyeing human hair by means of'oxidation dyes, particularly by means of heterocyclic amino compounds.
• the radical or group R is an aliphatic'radical having-not more than 10 carbon atoms, especially an alkyl group or a hydroxy-alkyl group having in each case one-four carbon atoms.
• Said alkyl group may be rectilinear or branched.
• Substitutents of the first orderdescribed above for the symbol R of the heterocyclic amino compounds of the formula (l) are, for example, the following: halogen atoms, especially chlorine or bromine atoms, rectilinear or branched alkyl groups containing one-four carbon atoms, substituted alkyl groups of said chain length, such as, for example, hydroxyalkyl groups or aminoalkyl groups, and also amino groups, amino groups substituted by alkyl radicals or alkanol radicals and also hydroxyl groups substituted by alkyl groups, such as --OCH or -C 'l-l
• halogen atoms especially chlorine or bromine atoms
• rectilinear or branched alkyl groups containing one-four carbon atoms substituted alkyl groups of said chain length, such as, for example, hydroxyalkyl groups or aminoalkyl groups, and also amino groups, amino groups substituted by alkyl radicals or alkanol radicals and also hydroxyl
• heterocyclic amino compounds'corresponding to the above formula (I) can be used in which X stands for one of the groups aminoindolenine; (Cl-lphd 2) CH,-CH-,, --CH CH(CH '-NR-CH,'-CH,-, -Cl-l,NR--CH O-CH,CH,; (R being Hor an alkyl group having one to four carbon atoms).
• amino compounds corresponding to the formula (I) in which X stands for the group CONH'- or NHCOCH As individual compounds, especially the following can be considered: 6- aminotetrahydroquinoline; l-methyl-6-aminotetrahydroquinoline; 1-methyl-6,8-diaminotetrahydroquinoline; l-methyl-6- amino-8-methoxytetrahydroquinoline; l-ethyl-6- aminotetrahydroquinoline; l-(B-hydroxyethyl)-6- aminotetrahydroquinoline; 4-methyl-7-aminodihydrobenzoxazine [,4); l-(B-hydroxyethyl)-2-methyl-5-aminoindolenine; 2-methyl-5-aminoindolenine; S-aminoindazolone-Ii; 7-amino- 2-oxo-tetrahydroquinoxaline; o-aminotetrahydroquinoxaline.
• Preparation of the amino compounds used is
• Known coupling components on the basis of aromatic compounds containing amino groups or hydroxyl'groups areQby way of example, diamines, phenols, naphthols, polyphenols and aminophenols. ln-thecase of diamines, aminophenols and phenols,-preferably-the orthoor meta-compounds are used.
• the coupling components are used "appropriately in about molecularquantities'with relation to'the'heterocyclic aminocompoundsHowever, itis, iii-"general, not detrimental if 'the latter are used in a certainexcessfln some-cases it has been found expedient to apply theheterocyclic amino compou'nds of the above-describedtype in'the form of salts with strong organic or inorganic acids, such *as oxalic acid, maleic' acid, sulfuric acid and hydrochloric acid.
• the use of the easily accessible hydrochlorides is preferred.
• Dyeing of the'hair is carried out in the temperature range of l'5-'40 C., preferably at ordinary room temperature.
• the hair dyes can be applied in the form of aqueous solutions, particularly however in form of a cream or emulsion.
• the dye components are mixed with any tensides, particularly anionic or nonionog'enic tensides'.
• Examples of tensides are especially alkylbenzeriesulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, additionproducts of'ethyleneoxide to fatty alcohols and alkylphenols.
• the absorptive power of the above-named dyes is good, even in mixture with such additions. Therefore,'t he hair dyes can be produced in the form of'shampoo's, particularly creamlike shampoos which are frequently demanded in practice.
• thickening agents such'as methylcellulose,starch. higher-fatty alcohols, Vaseline (petrolatum), Paraffin oil, and fatty acids, and also perfume oils or substances 'for the'care of the hair, e.g. pantothenic acid and cholesterol'may be admixed.
• the admixed material is applied in proportions which are conventional for therespective purpose.
• Wetting agents can be used especially in proportions of 05-30 percent by weight calculated on the total composition.
• Thickening agents are added in proportions of 01-25 percent by weight based on the weight of the total composition.
• EXAMPLE 1 Two parts by weight of -aminotetrahydroquinoline hydrochloride, 1 part by weight of a-naphthol and 1 part by weight of hydrogen peroxide are mixed with 96 parts water and adjusted to a pH value of 9.5 with ammonia. Gray human hair is treated with this solution for 20 minutes at 15 C. A deep dark blue coloration is thus obtained.
• a dyeing cream is prepared in the following manner: 1 part by weight of 1-(B-hydroxyethyl)-6-aminotetrahydroquinoline hydrochloride and 1 part by weight of 3-aminopyrazolone-5, are dissolved in an emulsion consisting of 10 parts by weight of fat alcohols having chain lengths of 16-18 carbon atoms, 10 parts by weight of fatty alcohol sulfate based on coconut oil and 70 parts of water and adjusted with ammonia to a pH value of 9. The resulting solution is mixed with 1 part of hydrogen peroxide and filled up with water to 100 parts by weight. If gray hair is treated with this dyeing cream thus prepared at 20 C., for 20 minutes, a red-violet coloration is obtained.
• room temperature is used herein to denote about 18 to 25 C.
• tensides is used to denote and include surfactants like alkylbenzenesulfonates (alkyl group C C fatty alcohol sulfates (C -C alkylsulfonates (C -C fatty acid ethanolamides (alkyl group C,,C addition products of ethylene oxide to fatty alcohols (C -C and alkylphenols (alkyl group C -C
• the weakly acid, neutral and alkaline pH values preferred in carrying out the invention are in the range from 3 to 10.
• the hydrogen peroxide used according to the above examples refers to hydrogen peroxide of percent concentration.
• the recitation atoms necessary for forming a heterocyclic nonaromatic five-membered (or six-membered) ring means radicals, comprising for example -(CH,),, (CH,) (CH CH(CH --NRCH CH -CH NR CH,,OCH CH (R being H or alkyl group having one-four carbon atoms).
• wetting agents and/or washing agents may be added to the dyeing creams used in carrying out the invention.
• Suitable examples are 0.5-30 percent by weight of alkylbenzene sulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, addition products of ethylene oxide to fatty alcohols and alkylphenols.
• a process for the dyeing of human hair which consists essentially of applying to said hair at temperatures ranging substantially from 15 to 40 C. and for a time sufficient to effect dyeing, an effective amount of an aqueous solution containing from 0.1 to 5 percent by weight of a mixture of a coupling component and a developer component in a mole ratio of 1:1 to 1:3 said coupling component being selected from the group consisting of aromatic diamines, phenols, naphthols, aminophenols, 3-methylpyrazoline-( 5 l-phenyl-3-methylpyrazolone-(S 1,3-dimethylpyrazolone-(5 3- aminopyrazolone-( 5 acetoacetic acid anilide, benzoylacetanilide, benzoylacettoluidide and nicotinoylacetanilide and said developer component being selected from the group consisting of l a heterocyclic amino compound of the formula NIIg wherein R, is a member selected from the group consisting of hydrogen, al,
• heterocyclic amino compound is in the form of an acid addition salt of a strong acid selected from the group consisting of inorganic and organic acids.
• aqueous solution has a further content of from 0.5 to 30 percent by weight of an agent selected from the group consisting of alkylbenzene sulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, ethylene oxide adducts of fatty alcohols and ethylene oxide adducts of alkylphenols.
• an agent selected from the group consisting of alkylbenzene sulfonates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethanolamides, ethylene oxide adducts of fatty alcohols and ethylene oxide adducts of alkylphenols.

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

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Family

ID=3618898

Family Applications (1)

Country Status (10)

Cited By (10)

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Citations (1)

• 1967
  • 1967-11-06 AT AT997767A patent/AT277464B/de not_active IP Right Cessation
• 1968
  • 1968-07-19 SE SE09944/68A patent/SE348368B/xx unknown
  • 1968-07-24 DK DK357768AA patent/DK120448B/da unknown
  • 1968-10-09 NL NL6814457.A patent/NL159880C/xx not_active IP Right Cessation
  • 1968-10-19 DE DE19681804066 patent/DE1804066B2/de active Granted
  • 1968-10-22 US US769749A patent/US3630655A/en not_active Expired - Lifetime
  • 1968-11-05 BE BE723373D patent/BE723373A/xx unknown
  • 1968-11-05 GB GB52357/68A patent/GB1223270A/en not_active Expired
  • 1968-11-05 FR FR1602547D patent/FR1602547A/fr not_active Expired
  • 1968-11-05 CH CH1646568A patent/CH537187A/de not_active IP Right Cessation

Patent Citations (1)

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