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US3485568A - 2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers - Google Patents

2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers Download PDF

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Publication number
US3485568A
US3485568A US671610A US3485568DA US3485568A US 3485568 A US3485568 A US 3485568A US 671610 A US671610 A US 671610A US 3485568D A US3485568D A US 3485568DA US 3485568 A US3485568 A US 3485568A
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US
United States
Prior art keywords
dihydroxy
dyeing
aminobenzene
human hair
diethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US671610A
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English (en)
Inventor
Gregoire Kalopissis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Application granted granted Critical
Publication of US3485568A publication Critical patent/US3485568A/en
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/415Aminophenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/30Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • D06P3/305Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes

Definitions

  • This invention relates to the. dycing of hair, furs and other keratinous fibers.
  • the known hair-dyeing processes are based almost exclusively upon the'us of a' hammer aromatic paradiamines and aminophe'nols, that is to say, on the use of intermediate bases which are converted by oxidation to it has beenfound that aqueous solutions of 2,4-dihydroxyaminobenzene and of 3,4-dihydroxyaminobenzene, in contradistinction to those of 2,S-dihydroxyaminobenzene, have an inconvenient color instability even at a pH of 7, and that their dyeing power decreases. and may even dis appear at the end of several months.
  • a process for dyeing live human hair, fur or other keratinous fibers which comprises impregnating said fibers with dyes which have a true dyeing action on;the. fiber, with the aid of modifiers such as metadiamines and phenols or polyphenols.
  • US. Patent 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 2,5 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.
  • aqueous dyeing compositions of this invention it is also possible to add to the aqueous dyeing compositions of this invention the conventional products employed in hair dyeing 'andintended 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 -'monornethylaminobenzene, 2,5 dihydroxy diethylaminobenzene and 2,5- dihydroxy-(/8-diethylaminoethyl) aminobenzene are novel per se and the invention includes these compounds and the processesfor theirproduction, 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 bydroxide and again extracted with methylisobutylketone. The product is distilled in vacuo. It passes over at C. under 0.1 mm. Hg pressure. The yield is of the order of 78%.
  • Example II In the same way as in Example I, there is prepared a solution containing:
  • 2,S-dihydroxy-diethylarninobenzene hydrobromide 3 Fatty alcohol C -C condensed with 2 mol of ethylene oxide, sulphated, sodium salt containing 20% of initial hydroxy-ethylenated alcohol g 4 5 N sodium hydroxide solution, q.s. for pH 7. Water, q.s. for cc 100 When this solution is applied to grey hair for 20 minutes, and then rinsed and dried, a pink-tinged light blond shade is obtained.
  • Example III When, under the same conditions as in Example II, there is applied to the hair a solution prepared from:
  • a dye composition for live human hair, fur and other keratinous fibers comprising an aqueous solution containing an effective dyeing amount of 2,5-dihydroxymonomethylarninobenzene or its acid addition salt and having a pH of about 3 to 10.
  • a dye composition for live human hair, fur and other keratinous fibers comprising an aqueous solution containing an effective dyeing amount of 2,5-dihydroxydiethylaminobenzene or its acid addition salt and having a pH of about 3 to 10.
  • composition of claim 1 wherein said compound is in the form of its acid addition salt.
  • composition of claim 2, wherein said compound is in the form of its acid addition salt.
  • a process for dyeing live human hair, fur and other keratinous fibers which comprises the steps of impregnating said fibers with dyeing amounts of the composition of claim 1 and allowing oxidation of the compound to take place on the fibers by exposing the same to air or an oxidizing agent.

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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)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US671610A 1961-09-25 1967-09-29 2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers Expired - Lifetime US3485568A (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
US3485568A true US3485568A (en) 1969-12-23

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 Before (1)

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

Country Status (7)

Country Link
US (2) US3546294A (no)
CH (1) CH382376A (no)
DE (1) DE1492062C3 (no)
FR (1) FR80568E (no)
GB (1) GB951509A (no)
IT (1) IT972004B (no)
NL (2) NL110373C (no)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4212645A (en) * 1974-01-18 1980-07-15 Lever Brothers Company Hair dyeing composition containing an aryldiamine and a substituted catechol

Citations (2)

* 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

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3214472A (en) * 1962-08-29 1965-10-26 Oreal N-(substituted-phenyl)-2, 4-dihydroxy-anilines

Patent Citations (2)

* 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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4212645A (en) * 1974-01-18 1980-07-15 Lever Brothers Company Hair dyeing composition containing an aryldiamine and a substituted catechol

Also Published As

Publication number Publication date
GB951509A (en) 1964-03-04
CH382376A (fr) 1964-09-30
NL281188A (no)
NL110373C (no) 1964-11-17
DE1492062B2 (de) 1974-05-02
FR80568E (fr) 1963-05-17
IT972004B (it) 1974-05-20
US3546294A (en) 1970-12-08
DE1492062A1 (de) 1972-04-20
DE1492062C3 (de) 1974-12-19

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