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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

• THE PRIOR ART OBJECTS OF THE INVENTION object of the present invention is the development of a process for the dyeing of living human hair consisting essentially of treating human hair at a temperature of from 10 C. to 40 C. with an aqueous dyestufi composition containing, as sole dyestutf ingredient, from 0.3% to by weight of a nitropyridine having the formula NH Y Y wherein Y is selected from the group consisting of NH;; and
• R is a member selected from the group consisting of alkyl having 1 to 8 carbon atoms, alkoxyalkyl having 2 to 8 carbon atoms, hydroxylalkyl having 2 to 8 carbon atoms, aminoalkyl having 2 to 8 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, dialkylaminoalkyl having 3 to 12 carbon atoms, alkylaminoalkyl having 2 to 8 carbon atoms, dialkanolaminoalkyl' having 5 to 12 carbon atoms and alkanolaminoalkyl having 3 to 8 carbon atoms;
• a further object of the present invention is the development of an aqueous composition for dyeing living 3,826,608 Patented July 30, 1974 human hair consisting essentially of at least by weight of water, from 0.5% to 55% by weight of customary dyestuif adjuvants, no chemical oxidizing agents and from 0.3% to 5% by Weight of a nitropyridine having the formula NH Y wherein Y is selected from the group consisting of -NH;; and
• R is a member selected from the group consisting of alkyl having 1 to 8 carbon atoms, alkoxyalkyl 2' to 8 carbon atoms, hydroxyalkyl having 2 to 8 carbon atoms, ,aminoalkyl having 2 to 8 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, dialkylaminoalkyl having 3- to 12 carbon atoms, alkylaminoalkyl having 2 to 8 carbon atoms, dialkanolaminoalkyl having 5 to 12 carbon atoms and alkanolaminoalkyl having 3 to 8 carbon atoms;
• R is a member selected from the group consisting of hydrogen and R and R and R taken together are selected from the group consisting of alkylene having 4 to 5 carbon atoms, ethoxyethylene and ethylaminocthylene, said aqueous composition having a pH of from about 8 toabout 10.
• a yet further object of the present invention is the obtention of a 3-amino-5-nitropyridine having the formula NO N H:
• R and R are members selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 2 to 4 carbon atoms, and when taken to: gether, alkylene having 4 to 5 carbon atoms.
• N 1 wherein X and Y are amino or substituted amino groups, possibly heterocyclic with the nitrogen atom.
• the substituents X and Y can be identical ordifferent.
• substituted amino groups of the formula can be used where R denotes an alkyl radical with 1 to 8, preferably 1 to 4 carbon atoms, which contains, preferably terminal alkoxy, amino or amino group substituted by alkyl or alkanol radicals, and where the alkyl radical or the alkanol can contain 1 to 4 carbon atoms, and where R, denotes a hydrogen atom or a radical as indicated for R R and R; can, together with the nitrogen atom, also represent a heterocyclic ring.
• Suitable substituted amino groups according to the compounds of formula I which contain heterocyclic rings are the pyrolidino, pipen'dino, or morpholino groups.
• R is a member selected from the group consisting of alkyl having 1 to 8 carbon atoms, alkoxyalkyl having 2 to 8 carbon atoms, hydroxyalkyl having 2 to 8 carbon atoms, aminoalkyl having 2 to 8 carbon atoms, cycloalkyl having to 8 carbon atoms, dialkylaminoalkyl having 3 where Z denotes an aminoor a substituted amino group, which likewise form a heterocyclic ring.
• R is a member selected from the group consisting of alkyl having 1 to 8 carbon atoms, alkoxyalkyl having 2 to 8 carbon atoms, hydroxyalkyl having 2 to 8 carbon atoms, aminoalkyl having 2 to 8 carbon atoms, cycloalkyl having to 8 carbon atoms, dialkylaminoalkyl having 3 where Z denotes an aminoor a substituted amino group, which likewise form a heterocyclic ring.
• S-amino-S-nitropyridines having the formula NO NH wherein R and R are members selected from the group consisting of alkyl having 1 to 4 carbon atoms, hydroxyalkyl having 2 to 4 carbon atoms, and, when taken together, alkylene having 4 to 5 carbon atoms.
• nitropyridines used can be produced in various ways. For example, monohalogen pyridines can be reacted in the presence of dimethyl sulfoxide with the corresponding amines or alkanol amines. Subsequently, two nitro groups are introduced by nitration, of which one is converted to an amino group by reduction, for example, with ammonium sulfide. The corresponding amino halogen-pyridines can also be utilized as starting material, where the amino groups can be substituted, if necessary.
• nitrating hydroxyaminopyridines substituted on the amino-function if necessary, chlorinating the hydroxy group with phosphorus oxychloride to obtain nitro-chloro-aminopyridines, and converting the latter as above, for example, in dimethyl sulfoxide with amines or alkanol amines to the desired susbtituted diarnino nitropyridines.
• nitro groups can also be effected in some cases with advantage by nitrosating and subsequent oxidation with ammoniacal hydrogen peroxide.
• 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 especially in the form of creams or emulsions.
• the nitropyridine compounds are mixed with an 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 fatty acids 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, vaseline, paraflin 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% to 30% by weight, and of thickeners, are 0.1% to 25% by weight, referred in each case to the total composition.
• concentration of the dyestufi components is, to a certain extent dependent on the purpose of use and'a'mounts, from 0.3% to 5% by weight, preferably 0.5% to 2.5% 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.
• EXAMPLE IV 4 parts by weight of cetyl alcohol, 4 parts by weight of stearyl alcohol, 3 parts by weight of lauryl alcohol and parts by weight of sodium lauryl ether sulfate were melted together at 70 C., and an aqueous alcoholic solution of 1 part by weight of 2,6-diamino-3-nitropyridine was stirred into this mixture.
• the cream was brought with hot water to 98 parts by weight, cooled to room temperature, adjusted to a pH of 9.5 with concentrated ammonia, to obtain 100 parts by weight.
• the dye cream so obtained dyed grey hair an intense yellow when treated at room temperature over a period of minutes. After the dye treatment, the hair was rinsed with water and shampooed.
• EXAMPLE V 5 parts by weight of cetyl alcohol, 4 parts by weight of stearyl alcohol, 1 part by weight of lauryl alcohol and 18 parts by weight of a mixture of fatty alcohol sulfates (C to C were melted at 70 C. and a solution of 1 part by weight of 2-pyrrolidino-3-amino-5- nitropyridine in some ethyl alcohol was stirred in.
• the cream was brought with hot water to 98 parts by weight, cooled to room temperature and adjusted to a pH of 9.5 with concentrated ammonia, to obtain 100 parts by weight.
• the dye cream so obtained dyed grey hair orange when treated at a temperature of 30 C. for 25 minutes.
• EXAMPLE VI A hair dyeing cream was produced as in Example 4, but, as a nitropyridine compound 1 part by weight of 2-dimethylamino-3-arnino-5-nitropyridine was utilized. The cream dyed grey hair yellow when treated at room temperature over a period of 30 minutes.
• a .process for the dyeing of human hair consisting essentially of applying to human hair at a temperature of from 10 C. to 40 C. an etfective amount of an aqeuous dyestuflf composition containing, as sole dyestutf ingredient, from 0.3% to 5% by weight of a nitropyridine having the formula NH Y wherein Y is selected from the group consisting of --NH, and
• R is alkyl having 1 to 8 carbon atoms;
• R is a member selected from the group consisting of hydrogen and R or R and R; taken together are alkylene having 4 to 5 carbon atoms, and rinsing said hair.
• nitropyridine is 2,6-diamino-3-nitropyridine.
• nitropyridine is a 3-amino-5-nitropyridine having the formula NO NH:
• R and R are alkyl having 1 to 4 carbon atoms, or, when taken. together, are alkylene having 4 to 5 carbon atoms.
• An aqueous composition for dyeing living human hair consisting essentially of at least 40% by weight of water, from 0.5% to 30% by weight of wetting agents, from 0.1% to 25% by weight of thickeners, and, as sole dyestufi ingredient, from 0.3% to 5% by weight of a nitropyridine having the formula NH Y wherein Y is selected from the group consisting of ---NH; and
• R is alkyl having 1 to 8 carbon atoms;
• R is a member selected from the group consisting of hydrogen and R or R and R taken together are alkylene having 4 to 5 carbon atoms, said aqueous composition having a pH of from about 8 to about 10.
• nitropyridine is 2,6-diamino-3-nitropyridine.
• nitropyridine is a B-amino-S-nitropyridine having the formula N0 NH:

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• 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)
• Pyridine Compounds (AREA)

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=5747149

Family Applications (1)

Country Status (8)

Cited By (4)

Families Citing this family (4)

• 1969
  • 1969-10-02 DE DE1949750A patent/DE1949750C3/de not_active Expired
• 1970
  • 1970-09-07 SE SE7012120A patent/SE375006B/xx unknown
  • 1970-09-07 NL NLAANVRAGE7013199,A patent/NL169679C/xx not_active IP Right Cessation
  • 1970-09-24 US US00075305A patent/US3826608A/en not_active Expired - Lifetime
  • 1970-09-24 CA CA093973A patent/CA923041A/en not_active Expired
  • 1970-09-29 FR FR7035098A patent/FR2064099B1/fr not_active Expired
  • 1970-10-01 CH CH1453170A patent/CH530790A/de not_active IP Right Cessation
  • 1970-10-01 GB GB1266816D patent/GB1266816A/en not_active Expired

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