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
  • A61Q5/10—Preparations for permanently dyeing the hair
• • 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

Definitions

• Substituted nitro-paraphenylenediamine products are well known as active ingredients in solutions for dyeing keratinic fibers and in particular for dyeing living hair.
• the alkyl and hydroxyalkyl groups are especially well known as substituents for modifying the shades which may be obtained with nitro-paraphenylenediamine itself.
• the object of the present invention is to provide a new dye which is a di-substituted derivative of nitro-paraphenylenediamine.
• This new dye is 1-amino-2-nitro-4-(2- hydroxyethyl)-methylaminobenzene, which has the formula:
• the invention also comprises two new methods of preparing the compound according to the above formula.
• the first of these methods of preparation is essentially characterized by the fact that 1-amino-2-nitro-4-methylaminobenzene is hydroxyalkylated by means of a halohydrin, for example. Hydroxyalkylation in the meta position of the nitro group can be effectuated in commercial quantities, without impurities, especially when using a bromohydrin.
• the second method of preparation according to the invention which makes it possible to obtain the compound according to Formula I is essentially characterized by the fact that 1-acetamino-4-(2-hydroXyethyl)-methylaminobenzene is nitrated with a sulfonitric mixture and that the resulting product is deacetylated by means of "ice broad limits, but falls preferably between 10 and 30 minutes.
• the temperature at which these dyes are applied may also be varied, but in most cases they are preferably applied at room temperature.
• the pH of these solutions is in general between 7 and 10 and preferably between 8 and 9.5.
• An alkali such as plain ammonia, or an organic base such as an alkylamine, an alkanolamine, or a heterocyclic amine may be used to adjust this pH.
• concentration of the dyes according to the invention may be varied, but this concentration is preferably between 0.1% and 3%.
• the new dye may be mixed with other nitro, azo or anthraquinone dyes, or any other dyes conventionally used for dyeing hair.
• a further object of the present invention is to provide a new method of dyeing keratinic fibers and especially human hair, which method is essentially characterized by the steps of applying to the hair a dyeing composition comprising in solution at least one compound according to Formula I and leaving this composition in contact with the hair for from 10 to 30 minutes.
• the compound according to Formula I may also be used as a base product in the organic synthesis of tri-substituted derivatives of nitroparaphenylenediamine.
• the present invention therefore envisages as a particular method of using the compounds according to the invention, a process of synthesizing 1- methylamino-2-nitro-4-(2' hydroxyethyl)-methylamino benzene by using the compound of Formula I.
• This process is essentially characterized by the fact that benzenesulfochloride is reacted with the compound of Formula I so that the former becomes attached to the unsubstituted nitrogen atom.
• the resulting product is treated with methyl sulfate in an alkaline medium, and the sulfonylbenzene radical fixed in the first step of the process is removed by hydrolysis in a hydrochloric acid medium.
• the present invention also envisages, as a particular use for the compound according to the invention, a process of preparation which makes it possible to synthesize 1-(2- hydroxyethyl)-amino 2 nitro-4-(2' hydroxyethyl)- methylaminobenzene.
• This process is essentially characterized by the fact that chloroethyl-chloroformate is reacted with the compound according to Formula I to yield the fi-chloroethylic ester of [2-nitro-4-(2'-hydroxyethyl)- methylamino]-phenylcarbamic acid and this ester is then hydrolyzed with caustic potash purified by solution in alcohol.
• EXAMPLE 1 First method of preparing l-amino-2-nitro-4-(2'- hydroxyethyl) -methylamino'benzene
• One mol (167 g.) of 1-amino-2-nitro-4-methylaminobenzene' is mixed with 1000 cm. of water and 60 g. of calcium carbonate.
• the mixture is boiled under reflux and 1.2 mols (150 g.) of glycol bromohydrin is added drop by drop, while stirring.
• 1500 cm. of boiling water is added, and after having continued the reflux for several minutes, the mixture is filtered through a funnel for hot filtration. After cooling, the filtrate yields 161 g. of the crude product, which, after two recrystallizations in methylisobutylketone, melts at C.
• Second step deacetylation and purificati0n.
• the acetylated derivative obtained in the first step is introduced into a mixture of 30 cm. of concentrated hydrochloric acid and 60 cm. of water. This is kept for /2 hour in a boiling water bath. A little animal black is added, the product is filtered, and after drying and cooling yields 16 g. of crystallized hydrochloride. This is dissolved in boiling water, which is rendered alkaline by adding ammonia, cooled, and on drying yields 13 g. of 1-amino-2-nitro-4-(2 hydroxyethyl) methylaminobenzene, whichafter recrystallization in chloroform, melts at 115 C.
• tosylatiom-A solution is prepared comprising 0.15 mol (31.65 g.) of 1-amino-2-nitro-4-(2'- hydroxyethyl)-methylaminobenzene in 110 cm. of pyridine. 0.15 mol (19.2 cm. of benzene-sulfochloride is added little by little, while stirring, at between 45 and 50 C. The reaction mixture is kept at 45 C.
• a composition for dyeing keratinic fibers comprising dyeing amounts of the compound of claim 1 in an aqueous solution having a pH between 7 to 10.
• composition as claimed in claim 2 in which the concentration of said compound lies between 0.1% and 3% inclusive.

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

Applications Claiming Priority (1)

Publications (1)

Family

ID=19724261

Family Applications (1)

Country Status (6)

Cited By (3)

Families Citing this family (3)

Citations (6)

• 1965
  • 1965-04-26 LU LU48468A patent/LU48468A1/xx unknown
• 1966
  • 1966-04-15 AT AT357966A patent/AT274782B/de active
  • 1966-04-15 AT AT302568A patent/AT276636B/de active
  • 1966-04-15 AT AT302668A patent/AT273070B/de active
  • 1966-04-21 US US544094A patent/US3549303A/en not_active Expired - Lifetime
  • 1966-04-25 DE DE1569815A patent/DE1569815C3/de not_active Expired
  • 1966-04-25 DE DE1569812A patent/DE1569812C3/de not_active Expired
  • 1966-04-25 DE DE1966O0011628 patent/DE1569813B2/de active Granted
  • 1966-04-26 GB GB18289/66A patent/GB1138171A/en not_active Expired
  • 1966-04-26 NL NL6605558A patent/NL6605558A/xx unknown

Patent Citations (6)

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