Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
  • C07C211/53—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
• • 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
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
  • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
  • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
  • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Definitions

• the invention relates to novel p-diaminobenzene derivatives and agents containing these compounds for dyeing keratin fibers.
• oxidation dyes have gained substantial importance.
• the coloration is formed by reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
• a suitable oxidizing agent for example, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol, 4-amino-3-methylphenol and 1,4-diaminobenzene are used as developer substances, while as coupler substances, for example resorcinol, 4-chlororesorcinol, 1- Naphthol, 3-aminophenol, 5-amino-2-methylphenol and derivatives of m-phenylenediamine are mentioned.
• DE-OS 100 14 855 describes colorants which contain p-phenylenediamines substituted as developers in the 2-position.
• Oxidative dyes used to dye human hair have many additional requirements in addition to the desired intensity of dyeing.
• the dyes must be harmless from a toxicological and dermatological point of view, and the hair dyeings obtained must have good fastness to light, durability, acid fastness and rubbing fastness. In any case, such dyeings must be stable for at least 4 to 6 weeks without exposure to light, friction and chemical agents stay.
• the present invention therefore relates to p-diaminobenzene derivatives of the general formula (I) or their physiologically compatible, water-soluble salts,
• R 1, R 2, R 3, R 4, R 5, R 6 and R 7 are independently hydrogen, a C 1 -C 6 -alkyl group, a C 2 -C 4 -hydroxyalkyl group, a
• Alkyl group C 3 -C 4 -dihydroxyalkyl group or a Ci-C4-alkoxy- (Ci-C 4), or R1 and R2 or R3 and R4 or
• R5 and R6 together with the N atom form a four-membered to eight-membered aliphatic ring, wherein at least two of the
• Radicals R 1 to R 7 are hydrogen
• R 8 is hydrogen or a C 1 -C 4 alkyl group
• R9 and R10 are each independently hydrogen, one
• Halogen atom a Ci-C 4 alkyl group, a Ci-C 4 -Hydroxyalkyl distr, a C- ⁇ -C 4 -Hydroxyalkoxy distr or a Ci-C 4 alkoxy group.
• Particularly preferred p-diaminobenzene derivatives of the formula (I) are 3- [3- (2,5-diaminophenyl) -allylamino] -aniline, 3- [3- (2,5-diamino-phenyl) -allylamino] - 6- (2-hydroxyethoxy) -aniline, 3- [3- (2,5-diaminophenyl) allylamino] -6-methyl-aniline and 3- [3- (2,5-diaminophenyl) -allylamino] -6- fluoroaniline or its physiologically acceptable salts.
• the compounds of the formula (I) can be used both as free bases and in the form of their physiologically tolerated salts with inorganic or organic acids, for example hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
• inorganic or organic acids for example hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
• the preparation of the p-diaminobenzene derivatives of the formula (I) according to the invention can be carried out using known synthesis methods, for example according to the following method.
• Ra represents a suitable protecting group as described, for example, in Organic Synthesis, Chapter 7, "Protection for the Amino Group", page 309 et seq., Wiley Interscience, 1991;
• Rb is NRIRa or NR1 R2;
• Rc is Ra or R6, and R1, R2, R5, R6, R7, R8, R9 and R10 are as defined in formula (I).
• the p-diaminobenzene derivatives of the formula (I) according to the invention are readily soluble in water and allow dyeings with high color intensity and excellent color fastness, in particular with regard to light fastness, wash fastness and rubbing fastness.
• the compounds of the formula (I) furthermore have excellent storage stability, in particular as a constituent of the colorants described below.
• Another object of the present invention are therefore agents for the oxidative dyeing of Keratinfasem, such as hair, furs, feathers or wool, especially human hair, based on a developer substance-coupler substance combination containing as developer at least one p-diaminobenzene derivative of the formula (I).
• the p-diaminobenzene derivatives of the formula (I) are present in the colorant according to the invention in a total amount of about 0.005 to 20 percent by weight, with an amount of about 0.01 to 10 percent by weight and in particular of 0.1 to 5 percent by weight being preferred is.
• coupler substances are preferably 2,6-diamino-pyridine, 2-amino-4 - [(2-hydroxyethyl) amino] -anisole, 2,4-diamino-1-fluoro-5-methyl-benzene, 2,4-diamino 1-methoxy-5-methylbenzene, 2,4-diamino-1-ethoxy-5-methylbenzene, 2,4-diamino-1- (2-hydroxyethoxy) -5-methylbenzene, 2,4 -Di [(2-hydroxyethyl) amino] -1, 5-dimethoxybenzene, 2,3-diamino-6-methoxy-pyridine, 3-amino-6-methoxy-2- (methylamino) -pyridine, 2.6 Diamino-3,5-dimethoxy-pyridine, 3,5-diamino-2,6-dimethoxy-pyridine, 1, 3-diamino-benzene, 2,4-diamino-1- (2-
• the advantageous properties of the p-diaminobenzene derivatives of the formula (I) described herein suggest it to be used as the sole developing agent, it is of course also possible to use the p-diaminobenzene derivatives of the formula (I) together with known developing agents, such as for example 1, 4-diaminobenzene, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, 4-aminophenol and its derivatives, for example 4-amino-3-methylphenol, 4,5-diaminopyrazole derivatives, for example 4, 5-diamino-1- (2-hydroxyethyl) pyrazole, 4,5-diamino-1-isopropyl-pyrazole or 4,5-diamino-1-pentyl-pyrazole, or Tetraaminopyrimidinen use.
• known developing agents such as for example 1, 4-diaminobenzene, 2,5-diaminoto
• the coupler substances and developer substances can in the colorant according to the invention in each case individually or in a mixture the total amount of Kuppler ⁇ substances and developing agents in the colorant of the invention (based on the total amount of the colorant) each about 0.005 to 20 weight percent, preferably about 0.01 to 5.0 weight percent and in particular 0.1 to 2, 5 percent by weight.
• the total amount of the developer-coupler substance combination contained in the colorant described herein is preferably about 0.01 to 20 weight percent, with an amount of about 0.02 to 10 weight percent and especially 0.2 to 6 weight percent being particularly preferred.
• the developer substances and coupler substances are generally used in approximately equimolar amounts; however, it is not disadvantageous if the developing agents are present in a certain excess or deficiency in this respect (for example, in a ratio of coupler substance to developing agent of 1: 2 to 1: 0.5).
• the colorant according to the invention may additionally contain other color components, for example 6-amino-2-methylphenol and 2-amino-5-methylphenol, as well as further conventional substantive dyes, for example triphenylmethane dyes such as 4 - [(4'-aminophenyl) - (4'imino -2 ", 5" - cyclohexadiene-1 "-ylidene) -methyl] -2-methylaminobenzene monohydrochloride (CI 42 510) and 4 - [(4'-amino-3'-methyl-phenyl) - (4" -imino-3 "-methyl-2", 5 "-cyclohexadiene-1" -ylidene) -methyl] -2-methyl-aminobenzene monohydrochloride (CI 42 520), aromatic nitro dyes such as 4- (2'-hydroxyethyl ) - amino-nitrotoluene, 2-amino-4,6-dinitrophenol, 2-amino
• the coupler substances and developers and the other color components if they are bases, in the form of physiologically acceptable salts with organic or inorganic acids, such as hydrochloric acid or sulfuric acid, or - if they have aromatic OH groups - in the form of Salts with bases, for example as Alkaliphenolate used.
• colorants if they are to be used for dyeing hair, other conventional cosmetic additives, such as antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, and perfume oils, complexing agents, wetting agents, emulsifiers, thickeners and conditioners may be included.
• antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite
• perfume oils such as perfume oils, complexing agents, wetting agents, emulsifiers, thickeners and conditioners may be included.
• the preparation form of the colorant according to the invention can be, for example, a solution, in particular an aqueous or aqueous-alcoholic solution.
• the particularly preferred preparation forms are a cream, a gel or an emulsion.
• Their composition is a mixture of the dye components with the usual additives for such preparations.
• Typical additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol or isopropanol, glycerol or glycols such as 1, 2-propylene glycol, wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, oxyethylated fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanolamides and ethoxylated fatty acid esters also thickeners such as higher fatty alcohols, starch, cellulose derivatives, petrolatum, paraffin oil and fatty acids, as well as also care substances
• constituents mentioned are used in the quantities customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 25 percent by weight and the conditioners in a concentration of about 0.1 to 5.0 weight percent.
• the colorant of the invention may be slightly acidic, neutral or alkaline.
• the colorant according to the invention has a pH of 5 to 11, 5, with a pH of about 6.5 to 10.5 being particularly preferred.
• the basic adjustment is preferably carried out with ammonia, but it is also possible to use organic amines, for example monoethanolamine and triethanolamine, or else inorganic bases such as sodium hydroxide and potassium hydroxide.
• inorganic or organic acids for example phosphoric acid, acetic acid, citric acid or tartaric acid come into consideration.
• the above-described coloring agent is mixed immediately before use with an oxidizing agent and a quantity sufficient for the hair dyeing treatment, depending on the amount of hair, generally about 60 to 200 grams, of this mixture to the hair.
• the oxidizing agent for the development of hair coloring are mainly hydrogen peroxide or its addition compounds of urea, melamine, sodium borate or sodium carbonate in the form of a 3- to 12prozentigen, preferably ⁇ prozentigen, aqueous solution, but also atmospheric oxygen into consideration.
• a ⁇ prozentige hydrogen peroxide solution is used as the oxidizing agent, the weight ratio between hair dye and oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent, especially at higher dye concentrations in Haarfetzbe ⁇ medium, or if at the same time a greater bleaching of the hair is intended used.
• the mixture is allowed to act on the hair at 15 to 50 degrees Celsius for about 10 to 45 minutes, preferably 30 minutes, then the hair is rinsed with water and dried.
• the hair is washed with a shampoo and eventually rinsed with a weak organic acid such as citric acid or tartaric acid. Then the hair is dried.
• hair colorants according to the invention containing diaminobenzene derivatives of the formula (I) as developer substance enable hair colorations with excellent color fastness, in particular with regard to light fastness, wash fastness and rubbing fastness.
• hair colorants according to the invention offer a wide range of different color shades, depending on the nature and composition of the color components. which ranges from blond to brown, purple, purple to blue and black hues. Here, the shades are characterized by their special color intensity.
• the very good dyeing properties of the hair dyeing compositions according to the present application are further demonstrated by the fact that these compositions enable the dyeing of graying, chemically undamaged hair without problems and with good hiding power.
• Dye D2 15.0 g Cetyl alcohol 0.3 g Ascorbic acid 3.5 g Sodium lauryl alcohol diglycol ether sulfate, 28% aqueous

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• Chemical & Material Sciences (AREA)
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• Cosmetics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 2004
  • 2004-09-04 DE DE102004042850A patent/DE102004042850A1/de not_active Withdrawn
• 2005
  • 2005-06-30 CA CA002578337A patent/CA2578337A1/en not_active Abandoned
  • 2005-06-30 JP JP2007528630A patent/JP2008511558A/ja not_active Withdrawn
  • 2005-06-30 AU AU2005282015A patent/AU2005282015A1/en not_active Abandoned
  • 2005-06-30 CN CNA2005800297750A patent/CN101090882A/zh active Pending
  • 2005-06-30 WO PCT/EP2005/007045 patent/WO2006027039A1/de active Application Filing
  • 2005-06-30 EP EP05763134A patent/EP1784382A1/de not_active Withdrawn
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• 2006
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