Classifications

• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/347—Phenols
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
  • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
  • C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms

Definitions

• the invention relates to an agent and a method for the oxidative dyeing of hair based on a substituted phenol of the general formula
• R 1 represents a hydroxyalkyl radical with 1 to 4 carbon atoms and R 2 represents a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, as a coupler substance.
• Oxidation dyes have become very important for hair coloring.
• the coloration arises from the reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
• Mainly 1,4-diaminobenzene, 2,5-diaminotoluene, 3-methyl-4-aminophenol and p-aminophenol are used as developer substances.
• the preferred coupler substances are ⁇ -naphthol, resorcinol, 4-chlororesorcinol, 2-methylresorcinol, m-aminophenol, 5-amino-o-k ⁇ esol and derivatives of m-phenylenediamine such as m-toluenediamine and 2,4-diaminoanisole.
• Oxidation dyes which are used to dye human hair, are subject to numerous special requirements. So they have to be safe from a toxicological and dermatological point of view and to achieve the desired coloration
• Allow intensity Furthermore, it is necessary that a wide range of different color shades can be produced by combining suitable developers and coupler components. In addition, good light, permanent wave, acid and rub fastness are required for the achievable hair coloring. In any case, such hair coloring must remain stable over a period of at least 4 to 6 weeks without exposure to light, chemical agents and rubbing.
• agents for the oxidative dyeing of hair which are a combination of developer substances known in hair dyeing with at least one substituted phenol of the general formula
• R 1 is a hydroxyalkyl radical with 1 to 4 carbon atoms and R 2 represents a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, also in the form of the phenolate with organic or inorganic bases, as a coupler substance, to an outstanding extent meet the task.
• the substituted phenols of the formula given as coupler substances in the hair colorants according to the invention are readily soluble in water with the addition of alkalis such as sodium hydroxide and, moreover, have an unexpectedly good shelf life, in particular as a constituent of the hair colorants according to the invention.
• alkalis such as sodium hydroxide
• suitable coupler substances of the formula given which are contained in the hair colorants according to the invention are in particular
• the coupler substances mentioned of which 2-hydroxymethyl-5-methylphenol and 3- ( ⁇ -hydroxyethyl) -6-methylphenol are preferred, in a concentration of about 0.01 to 3.0 percent by weight, in particular 0.1 to 2.0 percent by weight.
• the hair colorants can additionally contain known coupler substances, in particular ⁇ -naphthol, 3,4-diaminobenzoic acid, resorcinol, 4-chlororesorcinol, 2-methylresorein, m-aminophenol and 3-amino-6-methylphenol.
• coupler substances in particular ⁇ -naphthol, 3,4-diaminobenzoic acid, resorcinol, 4-chlororesorcinol, 2-methylresorein, m-aminophenol and 3-amino-6-methylphenol.
• 4-oxy-l, 2-methylenedioxy-benzene and 4-amino-1,2-methylenedioxybenzene can also be used advantageously as a coupler substance.
• 1,4-diaminobenzene, 2,5-diarainctoluene, 2,5-diaminoanisole, p-aminophenol and also come as a component of the hair colorants according to the invention 3-methyl-4-aminophenol into consideration.
• 2,5-Diaminobenzyl alcohol and 2- ⁇ ß-hydroxyethyl) -1,4-diaminobenzene can also be used advantageously as a developer substance.
• Both the substituted phenols of the formula given and the known couplers and developer substances used according to the invention can each be present in the hair dye alone or as a mixture with one another.
• the total amount of the developer substance-coupler substance combination contained in the hair colorants described here should be about 0.1 to 5.0 percent by weight, in particular 0.5 to 3.0 percent by weight.
• the developer components are generally used in approximately equimolar amounts, based on the coupler components. However, it is not disadvantageous if the developer component is present in a certain excess or deficit in this regard.
• the hair colorants of this application can additionally use other color components, for example 6-amino-3-methylphenol, 6-amino-2-methylphenol and 6-amino-3-ethoxyphenol, and also conventional direct dyes, for example triphenylmethane dyes such as Diamond Fuchsin (CI 42 510) and Leather Ruby HF (CI 42 520), aromatic nitro dyes such as 2-nitro-l, 4-diaminobenzene and 2-amino-4-nitrophenol, azo dyes such as Acid Brown 4 (CI 14 805) and Acid Blue 135 CC.I.
• anthraquinone dyes such as Disperse Red 15 (CI 60 710) and Disperse Violet 1 (CI 61 100), also contain 1,4,5,8-tetraamino-anthraquinone and 1,4-diamino anthraquinone.
• antioxidants such as ascorbic acid or sodium sulfite, perfume oils, complexing agents, wetting agents, emulsifiers, thickeners, care substances and others, can also be present in the hair colorants.
• the preparation form can be that of a solution, preferably a cream, a gel or an emulsion.
• Their composition is a mixture of the dye components with the constituents customary for such preparations.
• the usual constituents of creams, emulsions or gels are, for example, wetting agents or emulsifiers from the classes of anionic, cationic or nonionic surface-active substances such as fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, oxyethylated fatty alcohols, oxyethylated nonylphenols, fatty acid alkanolamides, further thickeners such as higher fatty alcohols, starch, cellulose derivatives, paraffin oil and fatty acids as well as care agents such as lanolin derivatives, cholesterol and pantothenic acid.
• ingredients mentioned are ver in the usual amounts for such purposes uses, for example, the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, while the thickeners can be contained in the preparations in an amount of about 0.1 to 25 percent by weight.
• the hair colorants according to the invention can react weakly acidic, neutral or alkaline.
• they have a pH in the alkaline range between 8.0 and 11.5, the setting preferably being made with ammonia.
• organic amines for example monoethanolamine or triethanolamine, can also be used.
• the hair colorants which contain a combination of developer substances known in hair dyeing with at least one substituted phenol of the stated formula as coupler substance and, if appropriate, additionally known coupler substances, are mixed with an oxidizing agent shortly before use and are worn Mix on hair.
• the main oxidizing agents used to develop hair color are hydrogen peroxide, for example as a 6% aqueous solution or its addition compounds with urea, melamine or sodium borate.
• the preparation of the 2-hydroxymethyl-5-methylphenol is based on the m-cresotinic acid available in industrial quantities, and this is esterified 1) into the corresponding m-cresotinic acid ester and reduced 2) with lithium aluminum hydride.
• 2-hydroxymethyl- ⁇ -methylphenol can be prepared from o-cresotinic acid.
• the hair colorants according to the invention offer a wide range of different color shades, which range from blonde to brown, ashy, purple, violet, golden to blue and matt colors.
• the colors are characterized by their special durability and fastness to wear.
• the observed coloring result is independent of the structure of the hair being dyed. This means that the shades achieved with the hair colorants according to the invention are easily reproducible.
• 50 g of the above hair dye are mixed shortly before use with 50 ml of hydrogen peroxide solution (6%) and the mixture is then applied to blonde human hair. After an exposure time of 30 minutes at about 40 ° C, rinsed with water and dried. The hair is colored with an intense shade of blue.
• this hair dye Shortly before use, 50 g of this hair dye is mixed with 50 ml of hydrogen peroxide solution (6%) and the mixture is left for 30 minutes Apply 40 ° C to blonde human hair. Then it is rinsed with water and dried. The hair has a gray-violet-bluish color.
• this hair dye 50 g of this hair dye are mixed with 50 ml of hydrogen peroxide solution (6%) shortly before use and the mixture is then applied to blonde human hair. After an exposure time of 30 minutes at 40 ° C rinsed with water and dried. The hair is colored light ash brown.

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• General Health & Medical Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Animal Behavior & Ethology (AREA)
• Emergency Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Coloring (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (1)

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ID=6106598

Family Applications (1)

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Cited By (1)

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Citations (3)

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• 1980
  • 1980-07-07 DE DE19803025715 patent/DE3025715A1/de not_active Withdrawn
• 1981
  • 1981-05-27 WO PCT/EP1981/000057 patent/WO1982000092A1/de not_active Ceased
  • 1981-05-27 EP EP81104079A patent/EP0043436B1/de not_active Expired
  • 1981-05-27 DE DE8181104079T patent/DE3160813D1/de not_active Expired
  • 1981-05-27 JP JP56501829A patent/JPS57501126A/ja active Pending
  • 1981-05-27 BR BR8108676A patent/BR8108676A/pt unknown
  • 1981-07-02 MX MX188136A patent/MX152694A/es unknown
• 1987
  • 1987-01-20 US US07/005,256 patent/US4755188A/en not_active Expired - Fee Related

Patent Citations (3)

Non-Patent Citations (3)

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