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
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes

Definitions

• R is selected from the group consisting of hydrogen and alkyl
• R is selected from the group consisting of hydroxy and alkyl
• R, which can be in position or 6 on the ring is selected from the group consisting of hydrogen, halogen, hydroxy and alkyl.
• This invention relates to improved compounds suitable for use in one step keratin fiber and hair dyeing.
• a number of compounds for dyeing keratinic fibers and notably hair are at present known, among the most commonly employed of these compounds are those which are oxidation dyes whose coloration results from polymerization under oxidizing conditions.
• the oxidation dyes employed are almost exclusively mixtures of aromatic diamines and aromatic aminophenols, generally known as bases, in combination with substances, generally called modifiers, such as substituted or unsubstituted monoand polyphenols. It is thus possible, by using a relatively limited number of aromatic bases and phenols, to obtain a fairly wide range of colorations, the proportions of the various constituents which enter into the composition of the dye bath being empirically varied.
• the formation of hair-coloring pigments from these mixtures results from a series of very complex chemical reactions which necessitate either the use of an oxidizing substance, hydrogen peroxide, or the presence of a substance having an alkaline reaction, which is generally ammonia. It is also known that by increasing the hydrogen peroxide and ammonia content there is obtained what is known as a decolorizing dye, there being simultaneously produced a decoloration of the hair to be dyed and a hair coloration in the desired shade.
• each of the selected bases employed develops its own shade. Consequently, an extensive range of commercially necessary shades may be made available merely by employing a number of these products, the final shade obtained being the component of the individual shades of the starting materials.
• the present invention provides new compounds which have the formula:
• R is selected from the group consisting of hydrogen and alkyl
• R is selected from the group consisting of hydroxy and alkyl
• R, which can be in position 5 or 6 on the ring is selected from the group consisting of hydrogen, halogen, hydroxy and alkyl.
• R and R are alkyls they are low molecular weight alkyls.
• a number of preferred compounds used in the composition of this invention are: 6 bromo- 4-methoxy-2- aminophenol, 6 methyl 4 methoxy Z-aminophenol, 4-methyl 5 hydroxy Z-methylaminophenol, 4-methyl- S-hydroxy 2 aminophenol, S-chloro 4 hydroxy-2- aminophenol, S-methyl 4 hydroxy 2 aminophenol, S-methoxy 4 hydroxy 2 aminophenol and 6-methyl- 4-hydroxy-2-aminophenol.
• the compounds are reduced by atmospheric oxygen.
• the dyeing solution may contain, in addition to the aforesaid compound or compounds, hydrogen peroxide and an alkali, in amounts which effect a decolorizing dyeing effect without modifying the dye compounds.
• the compounds of this invention make it possible to obtain greatly improved hair dyes that are color stable and do not require a modifier since each of the aforesaid bases develops its own shade as the result of air oxidation and it is possible to obtain all the shades required in practice by simply mixing two or more of these bases.
• these compounds may be stocked and brought into solution in the form of their salts, for instance in the form of their hydrochlorides or hydrobromides.
• a base such as ammonia is also 3 added to this solution the compounds are set free or activated at the time of use.
• Preferred hair dye compositions are aqueous solutions containing 1.75 to 3% by weight of the dye compound and which have a pH of 7 to 11.
• the corresponding nitro derivative crystallizes as it is formed and it is suflicient to separate it and to reduce it in the usual way by means of a mixture of tin and hydrochloric acid in order to obtain the hydrochloride of 6- bromo-4-methoxy-2-aminophenol which, when recrystallized from hydrochloric acid, takes the form of white crystals.
• EXAMPLE 2 Preparation of S-chloro-4-hydroxy-2-aminophenol This compound is prepared from chloro-dimethylhydroquinone which is nitrated in the usual manner with a mixture of sulphuric and nitric acids. After hydrolysis with caustic soda and acidification, 5-chloro-4-hydroxy-2-nitrophenol is filtered with suction. This nitro-derivative is reduced by hydrochloric acid and tin. After cooling the desired product, which crystallizes in the form of its hydrochloride with one molecule of water, is filtered with suction; it melts (dec.) at 163-166 C.
• EXAMPLE 3 Preparation of 5-methyl-4-hydroxy-2-aminophenol
• EXAMPLE 4 Preparation of 4-methyl-5-hydroxy-2-aminophenol is prepared using 2,4,5-trihyd roxytoluene which is left for a period of five days in a 6 N ammonia solution in an air-tight container. After acidification with hydrochloric acid and evaporation to dryness under vacuum, the residue is taken up in absolute alcohol and the inorganic salts are separated by filtration. The alcoholic filtrate is evaporated to dryness and the residue is dissolved again under heating in hydrochloric acid. On cooling the 2,4-dihydroxy aminotoluene crystallizes out with one molecule of water in the form of its hydrochloride.
• EXAMPLE 5 Preparation of 5-methoxy-4-hydroxy-2-aminophenol
• This product is prepared from methoxy-dimesylhydroquinone which is nitrated in the usual manner by means of a mixture of sulphuric and nitric acids, thus obtaining 4 2-methoxy-5-nitrochlorodimesylhydroquinone.
• This compound is then hydrolysed with a sodium hydroxide solution at a temperature of about 50 C., acidified and filtered to obtain 5-methoxy-4-hydroxy-Z-nitrophenol.
• This is then reduced with a mixture of tin and hydrochloric acid.
• On cooling the product crystallizes out with one molecule of water in the form of its hydrochloride and melts at 131 C. (dec.).
• EXAMPLE 6 Preparation of 4-methyl-5-hydroxy-2-methylaminophenol Trihydroxytoluene is left for a period of four days in an aqueous solution of monomethylamine in an air tight container. Acidification is then effected by means of hydrochloric acid, the solution is evaporated under vacuum and the residue is taken up in absolute alcohol. After filtration to eliminate the inorganic salts, the alcohol is evaporated and the desired product is obtained; it is recrystallized in the form of its hydrochloride in concentrated hydrochloric acid.
• EXAMPLE 7 Preparation of 6-methyl-4-methoxy-2-aminophenol A solution of m-cresidine is nitrated by addition of nitric acid in a mixture of acetic acid and acetic anhydride and a mixture of two isomeric nitro derivatives is obtained. After having desacetylated by refluxing with concentrated hydrochloric acid and after having cooled, the non-desired isomer is eliminated by filtration. By dilution of the mother liquid, 6-methy1-4-hydroxy-2-nitroaniline is precipitated; it melts at 130 C. This compound is dissolved in a diluted sodium hydroxide solution and it is deaminated by heating with reflux.
• 6-methyl-4-methoxy- 2-nitrophenol is then obtained, M.P. 94.5 C.
• the nitro derivative is then reduced into the corresponding amine by means of an alkaline sodium hydrosulfite solution.
• 6- methyl-4-methoxy-2-aminopheno1 is thus obtained; the hydrochloride melts with decomposition at 215-222 C.
• a dyeing solution according to the invention is prepared by mixing:
• a dyeing solution according to the invention is prepared by mixing:
• a dyeing solution according to the invention is prepared by mixing:
• This solution is applied to hair containing 90% white hairs. It is left in contact therewith for to minutes and, after washing and rinsing, the hair has a blond coloration.
• a dyeing solution according to the invention is prepared by mixing:
• the solution obtained is applied to light brown hair containing 70% of white hairs. After a contact period of minutes, the hair is rinsed and shampooed; the hair thus treated has a gold-blond coloration.
• a dyeing solution according to the invention is prepared by mixing:
• a dyeing solution according to the invention is prepared by mixing:
• a dyeing solution according to the invention is prepared by mixing:
• This solution is applied to hair containing 90% of white hairs and left in contact therewith for about 20 minutes. After rinsing and shampooing the hair is given a strong orange coloration.
• a dyeing solution according to the invention is prepared by mixing:
• This solution is applied to hair containing 90% of white hairs and left in contact therewith for about 20 minutes. After rinsing and shampooing the hair has a golden blond tint.
• a dyeing solution according to the invention is prepared by mixing:
• This solution is applied to hair containing 90% of white hairs and left in contact therewith for about 20 minutes. After rinsing and shampooing the hair has a copper blond tint.
• EXAMPLE 19 A dyeing solution according to the invention is pre pared by mixing: 6-methyl-4-hydroxy-2-aminophenol hydrobromide-2.5 g. Ammonia q.s. for pH 9.5.
• This solution is applied to hair containing 90% white hairs and left in contact therewith for about 20 minutes. After rinsing and shampooing, the hair has a mahogany tint.
• a dyeing solution according to the invention is prepared by mixing: 4-methoxy-2-aminophenol hydrochloride-0.15 g. 6-amino-4-diethylamino 2 aminophenol trihydrochloride0.15 g.
• This solution is applied to light brown hair containing 80% of white hairs. It is left in contact therewith for 20 minutes and after washing and rinsing the hair has a light gold-brown tint.
• a dyeing solution according to the invention is prepared by mixing: 4-methoxy-2-aminophenol-hydrochloride0.15 g. 6-amino-4 diethylamino 2 aminophenol trihydrochloride-0.15 g. 4-methoxy-2-amino-(fi-hydroxyethyl) aniline0.8 g.
• a dyeing solution according to the invention is prepared by mixing:
• 50 cc. of this solution are mixed with 50 cc. of hydrogen peroxide and applied to hair containing 90% of white hairs. After 25 minutes of contact, the hair is shampooed, rinsed and dried. It has a fiat golden blond tint.
• R is selected from the group consisting of hydrogen and methyl
• R is selected from the group consisting of hydroxy, methyl and methoxy
• R; which can be in position 5 or 6 on the ring is selected from the group consisting of chloride, bromine, hydroxy, methyl and methoxy, in which R can be methoxy only when R; is bromo or methyl in the 6 position, and R can be methoxy only when R is hydroxy.

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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)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (2)

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• 0
  • NL NL295194D patent/NL295194A/xx unknown
  • BE BE634643D patent/BE634643A/xx unknown
• 1963
  • 1963-07-10 DE DE19631492064 patent/DE1492064A1/de not_active Ceased
  • 1963-07-11 CH CH865463A patent/CH415965A/fr unknown
  • 1963-07-11 GB GB27554/63A patent/GB987342A/en not_active Expired
• 1967
  • 1967-06-12 US US645522A patent/US3546293A/en not_active Expired - Lifetime
  • 1967-06-12 US US645519A patent/US3666812A/en not_active Expired - Lifetime
  • 1967-06-12 US US645520A patent/US3558259A/en not_active Expired - Lifetime
• 1970
  • 1970-08-31 US US00068488A patent/US3738799A/en not_active Expired - Lifetime

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