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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/418—Amines containing nitro groups
• • 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
• • 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
  • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
• • 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
  • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil

Definitions

• the invention relates to a process for dyeing hair using direct hair dyes, a preparation which contains a leveling aid to increase the uniformity of the dye application being applied to the hair either before or simultaneously with the application of a direct hair dye.
• Direct hair dyes In addition to the oxidation dyes which are formed from oxidation dye precursors by oxidative coupling, the direct hair dyes play an important role in dyeing hair. Direct hair dyes have the advantage that they are used without the addition of oxidizing agents.
• the main direct dyes are nitrobenzene derivatives, e.g. B. nitrophenylenediamines and nitroaminophenols, antrachinone dyes, azo compounds and indophenols in question. Because of the lower fastness properties, direct dyes are mostly only used for temporary or semi-permanent hair dyeing.
• this goal can be achieved by a process for dyeing the hair, which is characterized in that a preparation is applied to the hair prior to or simultaneously with the application of a direct hair dye, which is used as an aid for increasing the uniformity of the color application contains a 5- or 6-membered heterocyclic ring compound which has a grouping of the formulas I - VI in the ring,
• ethylene 1,2-propylene, trimethylene, vinylene, propenylene, 1-ethanyl-2-ylidene, 1-propanyl-3-ylidene and 1-propenyl-3 -ylidene groups are understood.
• the preparation containing the leveling aid to be used according to the invention before the application of the direct hair dye this can preferably be done in the form of an aqueous preparation, e.g. B. a shampoo or conditioner, which the heterocyclic ring compound, possibly together with formulation aids and contains hair cosmetic active ingredients.
• the leveling aid is preferably contained in such a preparation in an amount of 0.1-5% by weight.
• further formulation auxiliaries include, in particular, water-soluble surface-active substances in an amount of 0.1-10% by weight, water-soluble, polymeric thickeners in an amount of 0.1
• hair cosmetic active ingredients such.
• leveling aid to be used according to the invention is to be applied to the hair at the same time as the substantive hair dye, a suitable heterocyclic ring compound is incorporated directly into the hair dye.
• the 5- or 6-membered heterocycles which are suitable according to the invention as leveling aids are predominantly known from the literature, and derivatives which may not be known from the literature can be easily synthesized by customary processes for the preparation of such ring systems.
• heterocyclic ring compounds from the group urazole, hexahydropyrimidin-2-one, 1,3-bis (2-hydroxyethyl) imidazolidin-2-one, imidazol-2-one, hydantoin, parabanic acid, barbituric acid , Pyrrolidin-2-one, imidazole, 2-aminoimidazole, 1,2,4-triazole, 2-aminopyrimidine, 2-aminothiazoline and 1,2,3-triazole are used as leveling agents.
• Particularly preferred among the 5- or 6-membered heterocyclic ring compounds mentioned are those which contain a group of the formula -NR 1 -CO-NR 1 - in the ring, in which R 1 is hydrogen, an alkyl group with 1-4 C- Atoms or a hydroxyalkyl group with 2-4 C atoms.
• the leveling aid is preferably contained in the preparation in an amount of 0.1-5% by weight.
• Suitable direct hair dyes are all dyes suitable for dyeing hair under physiologically acceptable conditions, ie in particular those dyes which attract hair keratin at temperatures below + 40 ° C. These are especially nitrobenzene dyes, e.g. B. nitrophenylenediamines, nitroaminophenols, antrachinone dyes, naphthoquinones and azo compounds.
• Suitable direct dyes for hair dyeing can be found in relevant manuals, e.g. B. from "The Chemistry of Synthetic Dyes” (edited by K. Venkataraman, Academic Press 1971 New York and London), Vol. V, Chapter VII (Hair Dyes), pages 507-529. Examples of suitable direct pulling hair dyes are e.g. B.
• the substantive hair dyes are usually contained in the preparations for hair coloring according to the invention in amounts of 0.05-5.0% by weight.
• the hair colorants according to the invention can also contain oxidation dye precursors for shading and producing natural shades.
• an oxidizing agent e.g. B. of hydrogen peroxide to initiate the oxidative development of the oxidation dye.
• the direct hair dye compositions according to the invention can also contain further auxiliaries. Among these, special mention should be made
• - Hair cosmetic active ingredients e.g. B. water-soluble, cationic polymers, glucose, D-panthenol, water-soluble proteins, protein degradation products or protein derivatives, cholesterol, vitamins, plant extracts, saponins or antiseborrheic agents and
• pH adjusting agents and buffer substances e.g. B. Triethanolamine, sodium citrate
• the direct dyes, the leveling aid and the other dyeing aids are incorporated into a suitable cosmetic carrier.
• the preparations according to the invention are aqueous solutions of the direct dyes, the leveling aid and possibly other auxiliaries.
• Gels, cream emulsions, shampoos, foam aerosols can also be used as carriers.
• Preferred carriers for direct dyes are setting agents, rinses and foaming aerosol preparations. The usual components of such carriers are water
• Emulsifier in amounts of 1 - 20% by weight
• - Solution brokers e.g. B. ethanol, isopropanol, 1,2-propylene glycol, glycerin, diethylene glycol monomethyl ether, butyl diglycol, polyethylene glycols in amounts of 1 - 10 wt .-%.
• Thickeners in particular water-soluble polymers in amounts of 0.1-2% by weight
• Preservatives e.g. B. p-hydroxybenzoic acid ester.
• the direct dyes are better absorbed on the undamaged hair areas, in particular in the area of the hairline, while the excessive coloring of severely damaged hair sections, in particular the hair tips, is markedly reduced.
• the following examples are intended to make this effect clear and to explain the subject matter of the invention in more detail without restricting it thereto.
• Hair dyes according to the invention were produced in the form of aqueous solutions, each containing 1% by weight of the direct dye and 1% by weight of the leveling heterocyclic ring compounds, dissolved in water (Examples 1 and 3). For comparison, hair colorants were produced without the addition of the leveling agent (Examples 2 and 4). Finally, an aqueous solution of 1% by weight of a leveling agent (Example 5) and, separately, a 1% solution of a direct dye was prepared (Example 6).
• the upper half of the strand of hair (the area of the hair tip) was treated with the aqueous solution of a cold waving agent based on ammonium thioglycolate for 30 minutes. After fixation (10 minutes, potassium bromate solution), the same half of the hair strand was ultrablonded with an aqueous solution of hydrogen peroxide and ammonium peroxide disulfate. Then treatment with the cold waving agent, fixation and ultrablonding was carried out again. The lower half of the hair strand (root area) was only ultrablonded once. In this way, two halves of hair strained to different degrees were obtained. The coloring solutions were left on the strands of hair at 27 ° C. for about 30 minutes, then washed out with a customary shampoo. After rinsing with water, the tresses were then dried.
• Each strand of hair was measured at eight points (4 in the area of the hairline and 4 in the area of the hair tip) using a color measurement system from Datacolor.
• the sample to be measured was fixed in a clamping device on the spectrophotometer and the reflectance values were measured over the range of visible light from 390 - 700 nm at a distance of 10 nm and processed by a computer (HP 2113 E mini computer).
• the computer program determined the standard color values according to the CIE system (Commission Internationale de l'Eclairage) according to DIN 5033 and converted them into color difference numbers according to DIN 6174.
• Example 5 The leveling agent solution of Example 5 was applied to a strand of hair of the type described above and pretreated in the same way, and after stripping off loosely attached solutions and drying the hair, the dyeing solution of Example 6 was applied (Examples 5 + 6). For comparison, a strand of hair without pretreatment with the leveling agent solution was only treated with the coloring solution of Example 6 (Example 6). The further tests were carried out as in Examples 1-4. 5. Results
• AT's leveling agent heterocyclic ring compound
• F1 1-hydroxy-2-amino-4,6-dinitrobenzene (picramic acid).
• the dyeings obtained with dyeing solutions 1 and 3 according to the invention and by the two-stage process (5 + 6) according to the invention show significantly smaller color differences between damaged and undamaged hair areas than the dyeings obtained without the use of leveling agents (examples 2, 4 and 6) and no perceptible color differences .

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (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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• 1989
  • 1989-09-02 DE DE3929173A patent/DE3929173A1/de not_active Withdrawn
• 1990
  • 1990-08-24 CA CA002066446A patent/CA2066446A1/en not_active Abandoned
  • 1990-08-24 JP JP2511746A patent/JPH05500048A/ja active Pending
  • 1990-08-24 KR KR1019920700440A patent/KR927002998A/ko not_active Application Discontinuation
  • 1990-08-24 EP EP90912646A patent/EP0489775A1/de not_active Withdrawn
  • 1990-08-24 WO PCT/EP1990/001420 patent/WO1991003231A1/de not_active Application Discontinuation
  • 1990-08-30 DD DD90343748A patent/DD297324A5/de not_active IP Right Cessation
• 1992
  • 1992-02-28 FI FI920897A patent/FI920897A0/fi not_active Application Discontinuation

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