US3546294A - 2,5-dihydroxy-monomethyl- or -diethylamino benzene and the salts thereof - Google Patents

2,5-dihydroxy-monomethyl- or -diethylamino benzene and the salts thereof Download PDF

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Publication number
US3546294A
US3546294A US671620A US3546294DA US3546294A US 3546294 A US3546294 A US 3546294A US 671620 A US671620 A US 671620A US 3546294D A US3546294D A US 3546294DA US 3546294 A US3546294 A US 3546294A
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US
United States
Prior art keywords
dihydroxy
dyeing
hair
solution
mol
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Expired - Lifetime
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US671620A
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English (en)
Inventor
Gregoire Kalopissis
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LOreal SA
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LOreal SA
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Publication date
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Publication of US3546294A publication Critical patent/US3546294A/en
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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
    • A61K8/415—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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • 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

  • This invention relates to compounds for dyeing hair, furs, and other keratinous fibers.
  • the known hair-dyeing processes are based almost exclusively upon the use of a mixture of aromatic paradiamines and aminophenols, that is to say, on the use of intermediate bases which are converted by oxidation to dyes which have a true dyeing action on the fiber, with the aid of modifiers such as metadiamines and phenols or polyphenols.
  • the formation, from these mixtures, of the coloring matter which has the dyeing effect results from a series of very complex chemical reactions.
  • the method necessitates, on the one hand, the use of an oxidizing substance, such as hydrogen peroxide, and the presence of a base, such as an alkali hydroxide, ammonia, etc. Consequently, the pH of these dyeing compositions is usually between 9 and 10.
  • US. Pat. 3,011,858 describes a process for dyeing live human hair, fur and other keratinous fibers which comprises impregnating the fibers with an aqueous solution of at least one dihydroxyaminobenzene selected from 2,S-dihydroxyaminobenzene, 2,4-dihydroxyaminobenzene and 3,4-dihydroxyaminobenzene, and acid addition salts thereof, and subjecting the impregnated fibers to the action of an oxidizing agent. It has been possible by this process to obviate or greatly to lessen, the aforesaid disadvantages.
  • new compounds for dyeing live human hair, fur or other keratinous fibers which comprises impregnating said fibers with an aqueous solution of at least one compound set forth below, and causing or allowing oxidation of the compound to take place on the fibers.
  • the hair, fur or other keratinous fiber is impregnated with an aqueous solution containing at least one compound of the above general formula, in contact with the air, the pH of the solution being between approximately 3 and 10.
  • the pH of the solution being between approximately 3 and 10.
  • New compounds of the above general formula which are particularly suitable for carrying out the process of the invention are: 2,S-dihydroxy-monomethylaminobenzene, 2,5-dihydroxy-diethylaminobenzene and 2,5-dihydroxy- B-diethylaminoethyl -aminobenzene.
  • aqueous dyeing compositions of this invention the conventional employed in hair dyeing and intended to increase the yield or to produce other effects, such as, for example, wetting agents, thickening agents, foaming agents, and reducing agents such as sodium sulphite.
  • the compounds 2,5 dihydroXy-monomethylaminoben zene, 2,S-dihydroxy-diethylaminobenzene and 2,5-dihydroxy-(fi-diethylaminoethyl)aminobenzene are novel per se and the invention includes these compounds and the processes for their production, referred to later herein, and also dyeing compositions containing them.
  • reaction mixture After cooling and extraction with methylisobutylketone to remove the unconverted products, the reaction mixture is made alkaline by the addition of 200 g. of 40% sodium hydroxide and again extracted with methylisobutylketone. The product is distilled in vacuo. It passes over at 130-135 C. under 0.1 mm. Hg pressure. The yield is of the order of 78%.
  • Example 11 In the same way as Example I, there is prepared a solution containing:
  • Example III When, under the same conditions as in Example II, there is applied to the hair a solution prepared from:

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US671620A 1961-09-25 1967-09-29 2,5-dihydroxy-monomethyl- or -diethylamino benzene and the salts thereof Expired - Lifetime US3546294A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR874113A FR80568E (fr) 1961-09-25 1961-09-25 Procédé pour teindre les cheveux, fourrures et autres fibres kératiniques

Publications (1)

Publication Number Publication Date
US3546294A true US3546294A (en) 1970-12-08

Family

ID=8763456

Family Applications (2)

Application Number Title Priority Date Filing Date
US671620A Expired - Lifetime US3546294A (en) 1961-09-25 1967-09-29 2,5-dihydroxy-monomethyl- or -diethylamino benzene and the salts thereof
US671610A Expired - Lifetime US3485568A (en) 1961-09-25 1967-09-29 2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers

Family Applications After (1)

Application Number Title Priority Date Filing Date
US671610A Expired - Lifetime US3485568A (en) 1961-09-25 1967-09-29 2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers

Country Status (7)

Country Link
US (2) US3546294A (en, 2012)
CH (1) CH382376A (en, 2012)
DE (1) DE1492062C3 (en, 2012)
FR (1) FR80568E (en, 2012)
GB (1) GB951509A (en, 2012)
IT (1) IT972004B (en, 2012)
NL (2) NL110373C (en, 2012)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1489344A (en) * 1974-01-18 1977-10-19 Unilever Ltd Hair dyeing composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1222700A (fr) * 1959-01-20 1960-06-13 Oreal Nouveaux dérivés aminohydroxylés aromatiques utilisables comme colorants d'oxydation, procédé de préparation et procédé d'utilisation de ces dérivés
US3011858A (en) * 1958-04-15 1961-12-05 Oreal Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes
US3214472A (en) * 1962-08-29 1965-10-26 Oreal N-(substituted-phenyl)-2, 4-dihydroxy-anilines

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3011858A (en) * 1958-04-15 1961-12-05 Oreal Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes
FR1222700A (fr) * 1959-01-20 1960-06-13 Oreal Nouveaux dérivés aminohydroxylés aromatiques utilisables comme colorants d'oxydation, procédé de préparation et procédé d'utilisation de ces dérivés
US3236734A (en) * 1959-01-20 1966-02-22 Oreal Process for dyeing hair with aromatic aminohydroxyl derivatives
US3214472A (en) * 1962-08-29 1965-10-26 Oreal N-(substituted-phenyl)-2, 4-dihydroxy-anilines

Also Published As

Publication number Publication date
GB951509A (en) 1964-03-04
DE1492062C3 (de) 1974-12-19
US3485568A (en) 1969-12-23
NL110373C (en, 2012) 1964-11-17
IT972004B (it) 1974-05-20
DE1492062A1 (de) 1972-04-20
DE1492062B2 (de) 1974-05-02
NL281188A (en, 2012)
CH382376A (fr) 1964-09-30
FR80568E (fr) 1963-05-17

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