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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
  • A61K8/355—Quinones
• • 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
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/22—Dyes with unsubstituted amino groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/264—Dyes with amino groups substituted by hydrocarbon radicals sulfonated
  • C09B1/268—Dyes with amino groups substituted by hydrocarbon radicals sulfonated only sulfonated in a substituent
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
  • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
  • C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
• • 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

Definitions

• the invention relates to agents for dyeing of human hair and, more particularly, to certain substituted anthraquinone dyes, as hereinafter will become more apparent. These dyes have the advantage that they can be employed substantially at room temperature.
• anthraquinone derivatives for the dyeing of human hair is known. These derivatives contain, e.g., amino-, hydroxyl-, carboxylor sulfo groups in the nucleus.
• novel hair dyes are characterized by a content of anthraquinone compounds which are free of acid groups in the nucleus and which contain a side chain consisting of a hydrocarbon radical connected to the nucleus by way of an oxygen or nitrogen atom, this hydrocarbon radical further containing a secondary or, preferably, tertiary nitrogen atom in an aliphatic chain or else in a heterocyclic ring.
• anthraquinone dyes especially those are suited which contain a hydrocarbon group of the formula wherein n equals 14, and X denotes one of the following groups: C H N; a)2; 2)a aZ
• These anthraquinone derivatives can be manufactured by reacting aminoanthraquinones which contain a reactive halogen atom, an N02 or OH group, with compounds which contain in an aliphatic chain or in a heterocyclic ring at least a secondary, but preferably a tertiary, nitrogen group.
• these compounds must contain a group capable of reacting with the substituted anthraquinone, e.g., an OH group, an NH group or a halogen atom.
• pyridine-Z-carbinol pyridine-2- 3,401,003 Patented Sept. 10, 1968 ethanol
• 4-pico1ylamine 2-picolylchloride; dimethylaminoethanol; N-beta-oxethylpropanediamine-( 1,3); ethanolisopropanolamine; diethylenetriamine; triethylenetetramine; beta-oxethylurea; beta-oxethylthiourea; 3-allyloxy 2 oxypropylamine (l); N-beta-aminoethylmorpholine; and N-beta-oxethylmorpholine.
• the aminoanthraquinone radical must be free from acid groups in the nucleus, such as hydroxyl-, carboxylor sulfo-groups. However, it may contain other substituents, such as halogen or nitro groups.
• the hair dyes can be mixed with any desired wetting, dispersing and washing agents, preferably however with those which are anionic or nonionic. Suitable wetting, dispersing and Wash ing agents are, e.g., alkylbenzenesulfates, fatty alcohol sulfates, alkylsulfonates, fatty acid ethan-olamides, ethylene adducts on fatty acids and fatty alcohols.
• the fixing quality of the dyes according to the invention remains good on the hair when admixed with the agents named above and does not diminish to any practical extent. Therefore, these dyes can be manufactured in the form of shampoos, particularly cream shampoos, which frequently are desirable in practice.
• thickeners such as methylcellulose, starch, higher fatty alcohols, Vaseline, paraffin oil, fatty acids; also essential oils and hair grooming agents, e.g., pantothenic acid and cholesterol, can be admixed.
• the additives are employed in the customary quantities.
• permanent waving agents also can be admixed to the novel hair dyeing agents.
• These permanent waving materials are based on compounds containing mercapto groups, e.g., thioglycolic acid, thiolactic acid, mercaptopropaneor mercaptobutanesulfonic acid.
• the novel hair dyes can be produced with these additives since the dyes have the advantage of stability even in the presence of the materials named so that storage presents no problem, even over prolonged periods of time.
• Human hair can be dyed with these novel hair dyeing agents without the aid of heating caps or similar devices since temperatures below 40 C., and preferably room temperature, are required for the dyeing process.
• the pH of the agents may range from 7 to 10, preferably from 8.5 to 9.5.
• the agents can be used for dyeing naturally grey hair or for redyeing dyed hair from one color to another. The hair thus dyed. is not affected by repeated washing nor -by rubbing or other friction.
• a permanent wave treatment is imparted to hair dyed with the agents according to this invention, a change in color or hue does not occur. Finally, the fixing of the color on the hair is very good.
• EXAMPLE 4 34 parts 1,4-diamino-S-nitroanthraquinone and 135 parts N-beta-oxethylpropanediamine-( 1,3) were reacted at 30 for 15 hours, and were allowed to stand for another 48 hours at room temperature. In contrast to the preceding example, no additon of NaOH was made. Thereafter, the reaction mixture was poured into 500 parts ice water, suction-filtered and dried. 33 parts of blue powder of Formula 4 thus were obtained:
• EXAMPLE 6 14.2 parts 1,4 diamino S-nitroanthraquinone were reacted with 100 parts diethylenetriamine at for 15 hours. The reaction mixture was poured into 1000 parts water and suction-filtered. After drying at 60 in vacuo, 15 parts of a dark blue powder were obtained having the Formula 6:
• EXAMPLE 7 14.2 pants 1,4 diamino S-nitroanthraquinone were reacted wtih 7.1 parts ;3oxethylthiourea (respectively 6.8 parts ,B-oxethylurea) and 2.4 parts powdered NaOH in 100 parts benzene at for 10 hours. Benzene was: removed in vacuo, the residue was treated with diluted HCl and suction-filtered. 15 parts of a blue powder were obtained having the following constitution as shown in Formula 7 respectively 8:
• n is a Whole number from 1 to 4 and X is selected from the group consisting of -C H N; -N(CH -NHCO-NH and NI-I-CSNH 5.
• a process for the dyeing of human hair which comprises applying to said hair for approximately 15 to 30 mintues and substantially at room temperature a cream having as the active ingredient 0.1 to 5 percent by weight, calculated on total composition, of 1,4-diaminoanthnaquinone free of hydroxyl-, carboxyland su1fo-groups in the anthraquinone ring; a hydrogen in said ring being replaced by an atom selected from the group consisting of oxygen and nitrogen; said atom being linked to a group wherein n is a whole number from 1 to 4 and X is selected from the group consisting of -C H N; -N(CH -NH-CONH and -NHCS-NH References Cited UNITED STATES PATENTS 3,123,605 3/1964 Turetzky et

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Emergency Medicine (AREA)
• Textile Engineering (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Engineering & Computer Science (AREA)
• Cosmetics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1963
  • 1963-09-04 DE DET24640A patent/DE1203915B/de active Pending
• 1964
  • 1964-07-13 NL NL646407966A patent/NL144831B/xx not_active IP Right Cessation
  • 1964-08-27 US US392586A patent/US3368942A/en not_active Expired - Lifetime
  • 1964-08-27 US US392607A patent/US3401003A/en not_active Expired - Lifetime
  • 1964-09-02 GB GB35863/64A patent/GB1005915A/en not_active Expired
  • 1964-09-02 GB GB35859/64A patent/GB1005913A/en not_active Expired
  • 1964-09-03 DK DK434864AA patent/DK112755B/da unknown
  • 1964-09-03 NL NL6410275A patent/NL6410275A/xx unknown
  • 1964-09-03 NO NO154628A patent/NO116772B/no unknown
  • 1964-09-03 BE BE652619D patent/BE652619A/xx unknown
  • 1964-09-04 CH CH1157864A patent/CH486245A/de not_active IP Right Cessation
  • 1964-09-04 SE SE10636/64A patent/SE324429B/xx unknown
  • 1964-09-04 SE SE10635/64A patent/SE320766B/xx unknown
  • 1964-09-04 FI FI1883/64A patent/FI42989B/fi active
  • 1964-09-04 LU LU46884D patent/LU46884A1/xx unknown
  • 1964-09-04 FI FI1882/64A patent/FI42859B/fi active

Patent Citations (5)

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