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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/347—Phenols
• • 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
  • 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
  • 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
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
  • A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
• • 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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
• • 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

• the invention relates to dyeing keratinic fibers with a l-amino-4-amino-benzene which can have halogen, alkyl or alkoxy groups on the benzene ring and a coupler selected from the group consisting of substituted phenols, R COCH COR and in which R and R are both Cl-I R is CH and R is OC H and R is phenyl and R is OOzH and Z is a sulphophenyl or chloro-sulphophenyl.
• This invention relates to new compositions for use in dyeing hair and to other keratinic fibers.
• the present invention provides a means of dyeing hair and other keratinic fibres by the conjoint use of p-diamines and certain couplers which produce dyestuffs that have exceptional stability to light for periods of the order of 12 months, which is an ample time with regard to the dyeing of human hair.
• the p-diamines of this invention are capable when used alone, of forming an intense coloration which may range from light brown to black, their association with the couplers of the invention brings about a formation of dyestuffs which are much more rapid than when the p-diamine is used alone. Consequently, the formation of the browns due to the pdiamine is insignificant as compared with the formation of the dye obtained by the p-diamine-coupler association,
• the dyeing compositions of the invention comprise a compound of Formula I and at least one coupler of 5 Formulas II, III or IV, the Formula I being:
• R represents OCH in the 4-position and R represents H or CH, in the 2-position, or
• R represents H or -CH in the 6-position and R in the 3-position is represented by: -CH -OCH NHCOCH NHCH CONH or NHCOCH N(C H or R represents CH in the 6-position and R represents a halogen in the 3- or 5-position;
• R and R are both CH or R represents CH and R represents OC H or R represents phenyl and R represents 00211 and Formula 1V being:
• Z represents a phenyl, 3-sulphophenyl, 4-su1- phophenyl or 2-chloro-5-sulphophenyl radical.
• X or Y is an alkyl or alkoxy radical it is preferably methyl, methoxy, ethyl or ethoxy; and where X or Y is halogen it is preferably chlorine.
• An essential feature of the invention resides in the fact that the ratio of the molecular concentration of the pdiamine to the molecular concentration of the coupler or couplers employed should be always less than unity.
• the dye compositions of the invention are conveniently used in the form of aqueous solutions having a pH of from 6 to 10.
• the compositions can contain dyestufis other than those of the invention, for instance ones which may be used under the same conditions as diirect dye- 3 stuffs, for example azo dyestuffs, or dyestuffs produced, in accordance with our French patent application No. 943,485 of Aug. 1, 1963, from the same couplers and an N-disubstituted p-diamine.
• the compositions can also con tain wetting agents, dispersing agents, penetration agents and other ingredients generally employed for hair dyeing.
• the dyeing solutions according to the invention provide a wide range of shades.
• use of couplers of Formula II gives blue shades
• couplers of the Formula III give yellow shades
• couplers of the Formula IV give red shades.
• the dyes formed by the inventive dye solutions have been found to be exceptionally resistant to ageing with no chemical evolution of the dyeing products obtained.
• the present invention has also for its object a new process of hair dyeing, said process being essentially characterized by that after having added hydrogen peroxide thereto, one applies on the hair a dyeing solution such as above defined, said hair being afterwards rinsed, shampooed, washed and dried.
• Ethyl alcohol 5 cc.
• Sodium hydroxide 0.02 g.
• Ammonia solution (22 Be.) 6 cc.
• Water, q.s. for 50 cc. This solution, which may be kept, is mixed with an equal volume of 6% hydrogen peroxide. The pH is 9.2. The mixture is then applied to white hair for 20 to 30 minutes. After shampooing, the hair is rinsed and dried. There is obtained a greyish purple-blue shade.
• Ammonia solution (22 Be.): 12 cc. Water, q.s. for 50 cc.
• the mixture is then applied to white hair for 20 to 30 minutes. After washing, rinsing and drying, a moderate yellow shade is obtained.
• This solution is mixed with an equal volume of hydrogen peroxide (6%).
• the pH is 9.5.
• the mixture is then applied to white hair for 20 to 30 minutes. After washing, rinsing and drying, there is obtained a light greyish-red shade.
• EXAMPLE 4 A solution having the composition given in Example 2 and a solution having the composition given in Example 3 are mixed in any proportions. An equal volume of hydrogen peroxide (6%) is then added, and the mixture is applied to white hair for 20 to 30 minutes. When the hair has been washed, rinsed and dried, there is obtained, depending upon the proportions in which the solutions of Examples 2 and 3 are employed, shades ranging from moderate yellow, through shades of orange to faint greyish-red.
• EXAMPLE 6 A solution having the composition given in Example 3 and a solution having the composition given in Example 1 are mixed in any proportions. An equal volume of hydrogen peroxide (6%) is added, and the mixture is applied to white hair for 20 to 30 minutes. When the hair has been Washed, rinsed and dried, a dyeing eifect ranging from faint greyish-purple-blue, passing through the purple shades, is obtained.
• the mixture is applied to white hair for 20 to 30 minutes. After washing, rinsing and drying, a dark greenish-blue tint is obtained.
• the mixture is applied to white hair for 20 to 30 minutes. After washing, rinsing and drying, a blueishgreen shade is obtained.
• Ammonia solution (22 Be.): 6 cc. Water, q.s. for 50 cc.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.6.
• the mixture is then applied to white hair for 20 to 30 minutes.
• a dark violet shade is obtained.
• Ammonia solution (22 Be.): 6 cc. Water, q.s. for 50 cc.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.6.
• the mixture is then applied to white hair for 20 to 30 minutes.
• the hair has been Washed, rinsed and dried, a greyish purple-red shade is obtained.
• the mixture is then applied to white hair for 20 to 30 minutes.
• the hair has been washed, rinsed and dried, there is obtained a greyish reddish-purple shade.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.3.
• the mixture is then applied to white hair for 20 to 30 minutes. When the hair has been washed, rinsed, and dried, there is obtained a dark blue shade.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.3.
• the mixture is then applied to white hair for 20 to 30 minutes.
• the hair has been Washed, rinsed, and dried, a dark blue shade is obtained.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.4.
• the mixture is then applied to white hair for to minutes. When the hair has been washed, rinsed, and dried, a dark blue shade is obtained.
• This mixture is applied to white hair for 20 to 30 minutes. When the hair has been Washed, rinsed and dried a greyish purple-blue shade is obtained.
• Ammonia solution (22 Be.) 8 cc. Water, q.s. for 50 cc. This solution is mixed with an equal volume of hydrogen peroxide (6%). The pH is 9.7.
• This mixture is applied to white hair for 20 to 30 minutes. When the hair has been washed, rinsed and dried, a faint reddish-brown shade is obtained.
• Aqueous solution of NH (24 g./l.): 50 co.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• This mixture is applied to white hair for 20 to 30 minutes. After the hair has been washed, rinsed and dried, a dark greyish-blue shade is obtained.
• 2,5-diaminotoluene 0.25 g. Hydrogen peroxide (20 vol.) 50 cc. Water q.s. for 100 cc.
• White hair is treated with a solution A and, after 20 minutes, the hair is rinsed and treated with solution B. After application for 20 minutes, the hair is washed, rinsed and dried.
• the dyeing effect obtained has a greenish-grey shade.
• White hair is treated with a solution A and, after 20 minutes, the hair is rinsed and treated with solution B. After application for 20 minutes, the hair is washed, rinsed and dried.
• the dyeing effect obtained has a pale green shade.
• This mixture is applied to white hair for to minutes.
• the hair has been washed, rinsed and dried, a moderate yellowish-brown dyeing effect is obtained.
• Ammonia solution (22 Be.) 8 cc. Water, q.s. for 50 cc.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.5.
• the mixture is applied to white hair for 20 to 30 minutes.
• the hair has been washed, rinsed and dried, there is obtained a dark reddish-brown dyeing effect.
• Ammonia solution (22 Be.): 12 cc. Water, q.s. for 50 cc. This solution is mixed with an equal volume of 6% hydrogen peroxide. The pH is 9.5.
• This mixture is applied to white hair for 20 to 30 minutes. After washing, rinsing and drying, a moderate yellow dyeing effect is obtained.
• Ammonia solution (22 Be.): 12 cc. Water, q.s. for 50 cc.
• This solution is mixed with an equal volume of 6% hydrogen peroxide.
• the pH is 9.0.
• This mixture is applied to white hair for 20 to 30 minutes.
• the pH is 9.0.
• This mixture is applied to white hair for 20 to 30 minutes. After washing, rinsing and drying, there is obtained a moderate olive-brown shade.
• Solutions A and B are mixed in any proportions, and there is added to this mixture an equal volume of 6% hydrogen peroxide.
• the pH is 9.6.
• Solutions A and B are mixed in any proportions, and there is added to the mixture obtained an equal volume of 6% hydrogen peroxide.
• the pH is 9.5.
• the mixture is then applied to 'white hair for 20 to 30 minutes.
• a dyeing eflect ranging from dark yellowish-blue to dark greenish-blue, depending upon the proportions of A and B.
• 2,4,4-triphydroxyazobenzene 0.5 g.
• Sodium hydroxide 0.08 g. Water, q.s. for 50 cc.
• R represents OCH in the 4-position and R represents H or CH in the 2-position, or
• R represents H or CH in the 6-position and R in the 3-position is represented by: CH OCH NHCOCH NHCH CONH NHCH CON (C 5) 2 0r or R represents CH in the 6-position and R represents a halogen in the 3- or 5-position;
• Formula 111 being:
• R and R are both CH or R represents CH and R represents OC H or R represents phenyl and R represents 1 1 and Formula IV being:
• Z represents phenyl, 3-sulphophenyl, 4-sulphophenyl or 2-chloro-5-sulphophenyl, in aqueous solution having a pH of 6-10.
• composition of claim 1, in which the said coupler is selected from the group consisting of 2,5-dimethylphenol, S-chloro 2 methylphenol, chloro-3-methyl-2- phenol, 3 N carbamylmethylaminophenol, 3-N-(N- diethylcarbamylmethyl) aminophenol, 2 methyl-S-N- carbamylmethylaminophenol, 4-methoxyphenol, 2-methyl- 4-methoxyphenol, Z-acetamino 4 methoxyphenol, 2- methyl 5 acetaminophenol, 3-acetaminophenol, 3-6- (N-diethylamino) acetaminophenol, Z-methyI-S-fi-(Ndimethyl)aminoacetaminophenol, 4 N benzoylacetaminobenzoic acid, 3-N-benzoylacetaminobenzoic acid, ethyl acetylacetate, acetyl acetone, 1-pheny1-3-methy1
• composition of claim 1, in which said p-diamine is selected from the group consisting of 1,2-dimethyl-3,6- diaminobenzene, 2,5-diaminotoluene, 2,5-diamino-4-methoxytoluene, 2,5-diaminoanisole, 4-chloro-2,5-diaminotoluene, 1,4-diaminobenzene hydrochloride, 1,3-dimethyl- 2,5-diaminobenzene and 4 amino-3-methyl-N- 3-sulphamidoethyl-aniline.
• composition of claim 1 which also contains hair treating amounts of hydrogen peroxide.
• a method of dyeing keratinic fibers which comprises applying to the fibers coloring amounts of the composition of claim 1.

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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)
• Epidemiology (AREA)
• Birds (AREA)
• Emergency Medicine (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Cosmetics (AREA)
• Coloring (AREA)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (8)

Cited By (16)

Families Citing this family (3)

• 1964
  • 1964-03-02 FR FR965802A patent/FR1426889A/fr not_active Expired
• 1965
  • 1965-02-25 US US435346A patent/US3563684A/en not_active Expired - Lifetime
  • 1965-02-26 CH CH266065A patent/CH436574A/fr unknown
  • 1965-02-26 DE DE1965O0010680 patent/DE1469790B2/de active Granted
  • 1965-03-01 AT AT177665A patent/AT267071B/de active
  • 1965-03-02 BE BE660519D patent/BE660519A/xx unknown
  • 1965-03-02 NL NL6502596A patent/NL6502596A/xx unknown
  • 1965-03-02 GB GB8931/65A patent/GB1079553A/en not_active Expired

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