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
  • A61K8/418—Amines containing nitro groups
• • 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
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

• Nitroparaphenylenediamine is a well known ingredient in hair dyeing solutions. This dye, when cold, has an excellent affinity for keratinic fibers, but is incapable of producing any colors other than red-orange shades.
• the purpose of the present invention is to alleviate this difiiculty by providing new dyes which produce even deeper shades, that is to say, tending more toward the blue, which may be used over a wider range of acid pH values.
• the object of the invention is therefore to provide a new article of manufacture which consists of a dye for keratinic fibers and especially for hair, which dye is essentially characterized by the fact that it contains at least one derivative of nitroparaphenylenediamine having the formula:
• R may represent hydrogen, or a methyl radical and R may represent either CH or the radical CH CH OH and n is a whole number falling between 1 and 4 inclusive.
• the dyes defined in this manner make it possible to obtain deep shades in the blue portion of the spectrum over a wide range of acid pH values and especially between pH 3 and pH 10.
• Another object of the present invention is to provide the new article of manufacture which consists of the new chemical compound derived from nitroparaphenylenediamine, and responding to the above formula.
• 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 fact that an aqueous solution comprising at least one dye responding to the above formula is applied to the hair, and that after from about 15 to minutes of application the hair is rinsed, shampooed, and dried.
• EXAMPLE 1 Preparation of monohydrochloride of 1-methylamino-2- nitro-4-carboxyrnethylamino benzene
• the method of preparing the above compound is new.
• -It is essentially characterized by the fact that l-rnethylamino-2-nitro-4-amino benzene is reacted with chloroacetamide to obtain 1-methylamino-2-nitro-4-carbamylmethylamino benzene, and that the amide function of the resulting compound is hydrolyzed with hydrochloric acid to yield the monohydrochloride of l-methylarnino-Z-nitro- 4-carboxymethylamino benzene.
• This process may be represented by the following diagram:
• EXAMPLE 2 Preparation of 1 methylamino-2-nitro-4-(N,N-1nethyl carboxymethyl) amino benzene
• the above compound is prepared by a new method essentially characterized by the fact that the primary amine function of 1 amino-2-nitro-4-N,N-methyl-carbamylamino benzene is blocked, using parato-luene sulfochloride, for example, after which a methyl radical is substituted for the free hydrogen remaining on this primary amine function, using for example methyl sulfate in a basic medium.
• the tosyl radical fixed in the first step of the process is then eliminated, using concentrated sulfuric acid, for example.
• EXAMPLE 4 Preparation of the monohydrochloride of l-methylamino- Z-nitro-B-carboxyethylamino benzene
• the above compound has been prepared by a new method essentially characterized by the fact that B- chloropropionamide is condensed on l-methylamino 2- nitro-4-amino benzene and that the amino function of the resulting product is hydrolyzed with hydrochloric acid to yield the monohydrochloride of l-methylamino 2- nitro-4-fl-carboxymethylamino benzene.
• This composition is applied to deep blond hair and left in contact therewith for 30 minutes. The hair is then shampooed and rinsed. A light violine chestnut shade results.
• This composition is applied to bleached straw-colored hair, and left in contact therewith for 15 minutes.
• the hair is then rinsed, shampooed, and rinsed again. After drying, the result is a beige with glints of burnt pearl.
• This composition is applied to bleached platinum blond hair, and left in contact therewith for 15 minutes. The hair is then rinsed, shampooed, rinsed again, and dried. A warm golden beige shade results.
• This composition applied to 100% white hair, for 20 minutes, produces after rinsing, shampooing and drying, a very light blond with a slightly pearlescent glint.
• the method of preparing the monohydrochloride of 1-( ,B-hydroxy-ethylamino)-2-nitro-4-(N ,N methyl-carboxymethyl)amino benzene which comprises the steps of reacting about 3 mols of chloroacetamide with each mol of the secondary amine function in the methylamine group of 1-amino-2-nitro-4-methylarnino benzene under reflux conditions, reacting about 1.2 mols of ,S-chloroethyl chloroformate with each mol of the resulting product under reflux conditions to obtain the ,B-chloroethylic ester of [2-nitro-4-(N,N-methyl carbamylmethyl)amino] phenylcarbamic acid, hydrolyzing the amide function of said ester, hydrolyzing the resulting product in an alkaline solution, and then acidify the resulting product.

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

Applications Claiming Priority (1)

Publications (1)

Family

ID=8577186

Family Applications (2)

Family Applications After (1)

Country Status (7)

Cited By (8)

Families Citing this family (1)

Citations (1)

• 1965
  • 1965-04-23 FR FR14482A patent/FR1458155A/fr not_active Expired
• 1966
  • 1966-04-20 BE BE679760D patent/BE679760A/xx unknown
  • 1966-04-21 CH CH1603467A patent/CH457482A/fr unknown
  • 1966-04-21 CH CH580066A patent/CH496444A/fr not_active IP Right Cessation
  • 1966-04-21 CH CH1603267A patent/CH457480A/fr unknown
  • 1966-04-21 US US544079A patent/US3532743A/en not_active Expired - Lifetime
  • 1966-04-21 CH CH1603367A patent/CH457481A/fr unknown
  • 1966-04-21 NL NL6605333A patent/NL6605333A/xx unknown
  • 1966-04-23 DE DE19661569809 patent/DE1569809A1/de active Pending
  • 1966-04-23 DE DE19661569811 patent/DE1569811A1/de active Pending
  • 1966-04-23 DE DE1617693A patent/DE1617693C3/de not_active Expired
  • 1966-04-23 DE DE19661569810 patent/DE1569810A1/de active Pending
  • 1966-04-25 GB GB18078/66A patent/GB1076915A/en not_active Expired
• 1970
  • 1970-07-20 US US56756A patent/US3676049A/en not_active Expired - Lifetime

Patent Citations (1)

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