Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/72—Nitrogen atoms
  • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• • 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
  • 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

• ABSTRACT Hair is dyed in a natural-looking color with a composition comprising acarrier compatible with hair in which at least one of the following compounds is dispersed in an effective amount:
• the present invention relates to a method and composition for dyeing keratin-containing material, for instance furs or living human hair and the like, and particularly for dyeing human hair in natural-looking colors.
• dyeing intermediates which may be oxidized to a dyestuff while in contact with the hair for a period of about 30 minutes.
• These dyeing intermediates may be such which may be oxidized per se, i.e. without the presence of a second dye intermediate, or these intermediates may belong to a group which must be oxidized in the presence of another dye intermediate and of an oxidizing agent in order to give the hair dye.
• Dye intermediates which alone cannot be oxidized to a hair dye are generally called nuancing dyes or modifiers.
• Such modifiers include for instance 4-aminodiphenylamine and 4,4-diaminodiphenylamine. These diphenylamines will serve to give a gray or bluish gray shade to oxidation hair dyestuffs which are formed of p-diaminobenzenes.
• difficulties are encountered due to the poor water solubility of the diphenylamines and, furthermore, only a limited depth of color can be achieved in this manner.
• These compounds may be produced by condensation of the aminopyridine derivative with the corresponding chloropyridine or chlorobenzene derivative.
• the method of producing the compounds is described for instanceon pages 105 and 1 17 of "Das Pyridin und seine Derivate by H. Maier- Bode and J. Altpeter, published by Wilhelm Knapp at Halle
• These compounds which are used according to the present invention are much more easily soluble in water than the analogous diphenylamine derivatives, and thus considerably stronger and more intensive hair colors or colorations of other keratin-containing material can be obtained according to the present invention.
• oxidation dye intermediates which may be used in combination with the bis-(pyridyDamines and pyridylarninobenzenes of the present invention are described, for instance, on page 504 of Cosmetic Science and Technology by E. Sagarin and include the following: p-phenylenediamine, p-toluylenediamine, m-phenylenecliamine, mtoluylenediamine, p-aminophenol, p-amino-N- dimethylaniline, 4,4-diaminodiphenylamine, 4-aminodiphenylamine, 4-amino-4'-oxydiphenylamine, m-diaminoanisole and m-diethylaminophenol.
• pyridine dyes are described in three German published applications, DAS 1,142,045, DAS 1,141,748 and DAS 1,149,496 and include the following: 2,6- diaminopyridine, 2,3-diaminopyridine, 4-methoxy-2,6- diaminopyridine, 4-ethoxy-2,6-diaminopyridine, 4-methy1- 2,6-diaminopyridine, 4-hydroxy-2,6-diaminopyridine, 3- hydroxy-2,6-diaminopyridine, 3-hydroxy-4-methyl-2,6- diaminopyridine, 3-hydroxy-4-methoxy-2,6-diaminopyridine, 6-hydroxy-4methyl-2,3-diaminopyridine, 6-methoxy-2,3- diaminopyridine, 6-ethoxy-2,3-diaminopyridine, 2,5- diarninopyridine, 2-dimethylamino-S-aminopyridine, 2- methyla
• the hair dyes formed according to the present invention may be used within a pH range of from 1.5 to 12.0 and preferably are used within a pH range from 3.0 to 10.0.
• EXAMPLE 1 The cream formed according to Example I is evenly brushed onto the hair and left in contact with the hair for 30 minutes. Thereafter, the hair is rinsed and dried. A light dull-brown color is obtained.
• EXAMPLE IB 80.0 grams of the cream of Example I are mixed with 20.0 ml. of 6 percent aqueous hydrogen peroxide and thereafter applied to gray hair. After contact with the hair for 30 minutes at body temperature, rinsing and drying, the hair will have an intensive dull brown color.
• EXAMPLE II A cream is produced according to Example I, utilizing, however, as dye intermediates: 2.0 grams p-toluylene-fiamino.
• EXAMPLE III A cream is produced according to Example I, using, however, as the dye intermediate 3.0 grams 6-amino-pyridylamino(2)- l ,4-diaminobenzene l-ICl of the formula:
• Dyeing hair with the thus-formed composition in accordance with Example [8 will result in a very natural-looking light ash-brown color.
• composition for dyeing hair comprising a alkaline aqueous suitable carrier compatible with the hair to be dyed and having distributed therethrough and dispersed therein an effective amount of at least one compound selected from the group consisting of:
• composition as defined in claim 1 and also including an effective amount of an oxidizing agent suitable for application to hair.
• composition as defined in claim 1 and also including an effective amount of an additional oxidation dye inter mediate.
• composition as defined in claim 3, wherein said additional oxidation dye intermediate is selected from the group consisting of p-phenylenediamine, p-toluylenediamine, mphenylenedia'mine, m-toluylenediarnine, p-aminophenol, pamino-N-dimethylaniline, 4,4-diarninodiphenylamine, 4- aminodiphenylamine, 4-amino-4'-hydroxydiphenylamine, mdiaminoanisole and m-diethylaminophenol.
• composition as defined in claim 3 and also containing an effective amount of an oxidizing agent suitable for application to hair.
• composition as defined in claim 1 wherein said compound is present in said carrier in an amount equal to between about 0.5 and 3 percent of the weight of said composition.
• composition as defined in claim 9, wherein said compound is selected from the group consisting of 2,5-diaminobis-(3,2"pyridyl) amine and the hydrochloride thereof.
• composition as defined in claim 9, wherein said compound is selected from the group consisting of 5-hydroxy-5- amino-bis-(2,2'pyridyl)amine and the hydrochloride thereof.
• composition as defined in claim 9, wherein said compound is selected from the group consisting of 6-aminopyridylamino(2)-l, l-diaminobenzene and the hydrochloride thereof.
• the method of dyeing hair which comprises applying to the hair an effective amount of the composition of claim l.
• the method of dyeing hair which comprises applying to the hair an effective amount of the composition of claim 2.

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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)
• Pyridine Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=7432678

Family Applications (1)

Country Status (4)

Cited By (9)

Families Citing this family (1)

Citations (2)

• 1963
  • 1963-04-19 DE DESCH33135A patent/DE1218116B/de active Pending
• 1964
  • 1964-04-17 AT AT337164A patent/AT253681B/de active
  • 1964-04-17 GB GB16024/64A patent/GB1025414A/en not_active Expired
• 1968
  • 1968-03-11 US US711906A patent/US3647351A/en not_active Expired - Lifetime

Patent Citations (2)

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