US3576587A - Method for dyeing hair and anthraquinone dyestuff composition - Google Patents

Method for dyeing hair and anthraquinone dyestuff composition Download PDF

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Publication number
US3576587A
US3576587A US741284A US3576587DA US3576587A US 3576587 A US3576587 A US 3576587A US 741284 A US741284 A US 741284A US 3576587D A US3576587D A US 3576587DA US 3576587 A US3576587 A US 3576587A
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US
United States
Prior art keywords
anthraquinone
hair
dyeing
composition
formula
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
US741284A
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English (en)
Inventor
Gregoire Kalopissis
Andree Bugaut
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LOreal SA
Original Assignee
LOreal SA
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Filing date
Publication date
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Publication of US3576587A publication Critical patent/US3576587A/en
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Classifications

    • 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
    • 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
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives

Definitions

  • the present invention relates to a new chemical compound responding to the following general formula:
  • n is a whole number lying between 2 and 6 inelusive.
  • the compound of Formula I is obtained by brominating l-N-acetylaminoalkylamino anthraquinone responding to the formula:
  • n has the significance hereinbefore indicated.
  • the present invention relates to a composition for dyeing keratinic fibers, and in particular human hair, which is essentially characterized by the fact that it comprises, in aqueous solution, at least one dye responding to Formula I.
  • the pH of the dyeing compositions according to the invention lies between 6 and 12, and is preferably about 9.
  • the concentration of the dyes of Formula I in the dyeing compositions according to the invention may vary within broad limits, but is preferably between 0.01% and 3%.
  • the dyeing compositions according to the invention may be used at temperatures between 5 and C., but are preferably applied at room temperature.
  • the dyeing compositions according to the invention may also contain wetting agents, dispersing agents, penetrating agents, perfumes and lacquers, and any other ingredients conventionally included in hair dyeing compositions. They may also contain other dyes than those responding to Formula I, and particularly anthraquinone, azo, and nitro dyes.
  • the present invention also relates to a method of dyeing keratinic fibers and particularly human hair, essentially characterized by the fact that the hair is impregnated with an aqueous solution containing at least one dye responding to the Formula I for from 5 to 30 minutes, after which it is shampooed, rinsed and dried.
  • Second step Preparation of l-q acetylaminopropylamino-4-hydroxy anthraquinone 0.0238 mole (9.5 g.) of 1-'y-acetylaminopropylamino-4- bromo anthraquinone is heated for 4 hours at 120 C. in the presence of 95 g. of fuming sulfuric acid and 4.75 g. of boric acid. After cooling, the reaction mixture is poured over cracked ice and neutralized with a sodium hydroxide solution. 10 cc. of of acetic anhydride is added and the mixture heated for 30 minutes at 70 C. After cooling, drying and washing with water yields 7.7 g. of 1 'y acetylaminopropylamino-4-hydroxy anthraquinone which, after recrystallization in chlorobenzene, melts at 198 C.
  • This composition is applied to bright golden chestnut hair, and left to act for 10 minutes, after which the hair is shampooed and rinsed. A violine chestnut is obtained.
  • n is an integer of 2-6 inclusive, said dye being present in amounts of about 0.01-3 weight percent of said composition, permitting said composition to remain in contact with said hair for a period of about 5-30 minutes,
  • composition for dyeing human hair comprising an aqueous solution of an anthraquinone dye having the formula wherein n is an integer of 2-6 inclusive, said dye being present in amounts of about 0.01 weight percent of said composition.
  • composition of claim 2 having a pH between 6-12.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US741284A 1967-07-05 1968-07-01 Method for dyeing hair and anthraquinone dyestuff composition Expired - Lifetime US3576587A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU54036 1967-07-05

Publications (1)

Publication Number Publication Date
US3576587A true US3576587A (en) 1971-04-27

Family

ID=19725266

Family Applications (1)

Application Number Title Priority Date Filing Date
US741284A Expired - Lifetime US3576587A (en) 1967-07-05 1968-07-01 Method for dyeing hair and anthraquinone dyestuff composition

Country Status (8)

Country Link
US (1) US3576587A (zh)
BE (1) BE716436A (zh)
CH (1) CH497176A (zh)
DE (1) DE1768725C3 (zh)
FR (1) FR1574275A (zh)
GB (3) GB1227824A (zh)
IT (1) IT1014006B (zh)
LU (1) LU54036A1 (zh)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4894451A (en) * 1985-04-01 1990-01-16 The University Of Vermont Unsymmetrical 1,4-bis(aminoalkylamino)-anthracene-9, 10-diones and derivatives
US5314505A (en) * 1991-11-01 1994-05-24 Clairol, Inc. Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain
WO2013135503A1 (de) * 2012-03-14 2013-09-19 Henkel Ag & Co. Kgaa Mittel zum färben und/oder mattieren von keratinhaltigen fasern enthaltend neuartige 1,4-diaminoanthrachinonfarbstoffe

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU60732A1 (zh) * 1970-04-15 1972-03-02
FR2361447A1 (fr) * 1976-08-12 1978-03-10 Oreal Composes colorants constitues de polymeres cationiques hydrosolubles et compositions tinctoriales les contenant
LU83177A1 (fr) * 1981-02-27 1982-09-10 Oreal Utilisation d'hydroxyanthraquinones pour la coloration des fibres keratiniques humaines,procede et composition les mettant en oeuvre

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1277495A (fr) * 1960-01-08 1961-12-01 Gen Aniline & Film Corp Colorants anthraquinoniques basiques et procédé pour leur fabrication

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4894451A (en) * 1985-04-01 1990-01-16 The University Of Vermont Unsymmetrical 1,4-bis(aminoalkylamino)-anthracene-9, 10-diones and derivatives
US5314505A (en) * 1991-11-01 1994-05-24 Clairol, Inc. Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain
WO2013135503A1 (de) * 2012-03-14 2013-09-19 Henkel Ag & Co. Kgaa Mittel zum färben und/oder mattieren von keratinhaltigen fasern enthaltend neuartige 1,4-diaminoanthrachinonfarbstoffe
US9259380B2 (en) 2012-03-14 2016-02-16 Henkel Ag & Co. Kgaa Means for dyeing and/or matting keratinic fibres containing novel 1,4 diaminoanthraquinone dyes

Also Published As

Publication number Publication date
LU54036A1 (zh) 1969-03-24
CH497176A (fr) 1970-10-15
FR1574275A (zh) 1969-07-11
DE1768725B2 (de) 1972-07-13
GB1227825A (zh) 1971-04-07
IT1014006B (it) 1977-04-20
DE1768725A1 (de) 1971-01-28
DE1768725C3 (de) 1973-02-15
GB1227826A (zh) 1971-04-07
BE716436A (zh) 1968-12-12
GB1227824A (zh) 1971-04-07

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