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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/415—Aminophenols
• • 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
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
  • D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes

Definitions

• oxidation dyes which are not true dyes but products which, on oxidation, give coloured derivatives.
• the known oxidation dyes are generally aromatic polyamines and/or polyaminophenols.
• oxidation dyes a solution of such a dye is mixed, a short time before use, with an oxidizing solution, for example dilute hydrogen peroxide, and the mixture is then applied to the hair to be dyed. Satisfactory results are obtained, but this method offers the disadvantages that the treatment is of excessively long duration, the hydrogen peroxide tends to act deleteriously on the substance of the hair during the application, and it is necessary to store the working solutions in separate bottles.
• R and R each represent a hydrogen atom, a lower alkyl group or a lower hydroxyalkyl group; and X represents a halogen atom, or an amine, hydroxyl, carboxyl, lower alkyl, lower alkoxy or nitro group, the nitro group with the additional feature that at least one out of the two radicals R R each represent a hydrogen atom, or else if X represents a hydrogen atom provided that at least one among said radicals R R is other than a hydrogen atom, have remarkable properties as oxidation dyes for the dyeing of animal fibres and more especially of the human hair.
• the said compounds oxidize rapidly in the air so that the use of an auxiliary oxidizing agent, such as hydrogen peroxide, is avoided, together with the concomitant disadvantages referred to above.
• a process for dyeing live hair comprises applying to the fibres a solution of a compound of the aforesaid general formula, allowing the oxygen of the ambient air to act on the hair impregnated with the compound for a time sufficient to the desired development of the shade, and thereafter rinsing the hair.
• aqueous solution of these compounds or of their derivatives is prepared, the pH of the solution is adjusted with the aid of an alkali, for example ammonium hydroxide, and the solution is applied to the fibres to be dyed, for example to the human hair.
• an alkali for example ammonium hydroxide
• the fibre is dyed to a shade depending upon the derivative chosen.
• the process is very simple, avoids the use of an oxidizing agent such as dilute hydrogen peroxide, and permits dyeing at room temperature.
• the present invention further provides compositions for application to animal fibres for dyeing the same, comprising an aqueous solution of a compound of the aforesaid general formula adjusted to a pH value of 5 to 8.
• This compound is nitrated by means of a mixture of concentrated nitric and sulphuric acids at a temperature below 5 C.
• the product is poured on to crushed ice and the precipitate obtained is filtered and washed with water. On recrystallization, there is obtained, in a yield of 6-nitro-2:4-diacetylarninophenol, melting at 214 C.
• This product is deacetylated by heating it on the Water bath in a hydrochloric acid medium for half an hour. Crystals of 6-nitro-2:4-diaminophenol monohydrochloride are obtained, in a yield of 76%.
• the pH of the solution is adjusted to a value of from 5 to 6 with the aid of an organic acid, such for example as citric acid.
• an organic acid such for example as citric acid.
• This hydrochloride is obtained in the form of a white powder which decomposes at about 225 C. to 230 C.
• Dyeing A 3% aqueous solution of this hydrochloride is prepared and is brought to BS by means of ammonia and immediately applied to the hair. On oxidation in contact wtih the ambient air, the hair is dyed a greenish blond.
• EXAMPLE IV 183 g. (1 mole) of 2:4-dinitroaniline are dissolved in 1200 ml. of glacial acetic acid. This solution is heated to 60 C. and a solution of 192 g. of bromine in 200 ml. of glacial acetic acid is gradually added. The mixture is maintained at the ter'iperature of 60 C. for 8 hours, and then allowed to cool. The bromo derivative, which crystallizes on cooling, melts at #153 54 C. The yield is about 70%. This bromo derivative (170 g.) is introduced into a round flask equipped with a reflux condenser and containing 1400 ml. of a 5% aqueous solution of potassium hydroxide.
• Dyeing-3 g. of 6-bromo-2:4-diaminophenol sulphate are dissolved in 100 ml. of water. At the time of application of this solution to live hair, it is adjusted to pH 8 by adding ammonia. After exposure to ambient air for 10 to minutes, the hair is dyed in a beautiful brown shade having a violet tinge.
• S-dinitrosalicylic acid is reduced by means of tin and hydrochloric acid. After neutralization and acidification by means of sulphuric acid, the sulphate is obtained as a white powder which is insoluble in water and difficultly oxidizable when dry. The yield is 60%.
• Dyeing.-3 g. of the powdered sulphate are introduced into ml. of water.
• the addition of ammonia immediately before the application to the hair and in sulficient quantity to bring the pH to 8 produced complete dissolution of the powder.
• the hair impregnated with the resulting solution is dyed a beautiful ash-blond shade on mere exposure to the air for :10 to 15 minutes.
• EXAMPLE VII 6-Methyl-2.'4-Diamin0phen0l 1130- NHQ 4-nitro-orthotoluidine is heated for several hours with a 15% potassium hydroxide solution. The corresponding phenol melting at 94 C. is quantitatively obtained. This phenol is treated with a sulphuric/nitric acid mixture to form the dinitro derivative. On reduction, the desired diamine is obtained, which is isolated in the form of its sulphate.
• a process for dyeing live human hair which comprises, applying thereto an aqueous solution as an oxidative dyestuff containing 6-nitro-2:4 diaminophenol, thereafter said hair is oxidized to promote the development of the dyestuif before the hair is rinsed.
• a process for dyeing live human hair which comprises, applying thereto an aqueous solution as an oxidative dyestuif containing 2:4:6-triaminophenol, thereafter said hair is aerated to promote substantial oxidation of this compound before being rinsed.
• a process for dyeing live human hair which comprises, applying thereto an aqueous solution as an oxidative dyestuff containing 1:2-dihyd1-0xy 3:5 diaminobenzene, thereafter said hair is aerated to promote substantial oxidation of this compound before being rinsed.
• a process for dyeing live human hair which comprises, applying thereto an aqueous solution as an oxidative dyestuff containing 6-methoxy-2:4-diaminophenol, thereafter said hair is aerated to promote substantial oxidation of this compound before being rinsed.
• a process for dyeing live human hair which comprises, applying thereto an aqueous solution as an oxidative dyestuif containing 3:5-diaminosalicylic acid, thereafter said hair is aerated to promote substantial oxidation of this compound before being rinsed.
• a process for dyeing live human hair which comprises, applying thereto an aqueous solution as an oxidative dyestuff containing 6 methyl 2:4 diaminophenol, thereafter said hair is aerated to promote substantial oxidation of this compound before being rinsed.

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• 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)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Cosmetics (AREA)
• Coloring (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=26213974

Family Applications (1)

Country Status (3)

Cited By (5)

Citations (4)

Family Cites Families (4)

• 1956
  • 1956-08-04 DE DES49849A patent/DE1096552B/de active Pending
  • 1956-11-21 CH CH348783D patent/CH348783A/fr unknown
• 1959
  • 1959-12-07 US US857988A patent/US3134721A/en not_active Expired - Lifetime

Patent Citations (4)

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