US3632292A - 1-methylamino-2-nitro-4-(2{40 -hydroxyethyl)-methylaminobenzene for dyeing human hair - Google Patents

1-methylamino-2-nitro-4-(2{40 -hydroxyethyl)-methylaminobenzene for dyeing human hair Download PDF

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Publication number
US3632292A
US3632292A US508578A US50857865A US3632292A US 3632292 A US3632292 A US 3632292A US 508578 A US508578 A US 508578A US 50857865 A US50857865 A US 50857865A US 3632292 A US3632292 A US 3632292A
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US
United States
Prior art keywords
hair
nitro
dyeing
methylaminobenzene
methylamino
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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
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US508578A
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English (en)
Inventor
Gregoire Kalopissis
Andree Bugaut
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LOreal SA
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LOreal SA
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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/418—Amines containing nitro groups
    • 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
    • C09B51/00—Nitro or nitroso dyes

Definitions

  • ABSTRACT An improved dye compound l-methylamino-Z- nitro'-4-(2'-hydroxyethyl)-methylaminobenzene and a method of making it.
  • Nitroparaphenylenediamine is a known active ingredient used in dyes for living hair.
  • trihydroxyalkylated derivatives of nitroparaphenylenediamine has been suggested, and especially those trihydroxyethyls having a hydroxyethyl radical on the amino group in the ortho position of the nitro group and two hydroxyethyl radicals on the amino group in the meta position of the nitro group.
  • the object of the present invention is to provide a new nitrated hair dye and the coloring compositions which can be made with this new dye.
  • the new dye is 1-methylamino-2-nitro-4-(2-hydroxyethyl)- methylaminobenzene.
  • the invention also comprises a method of manufacturing this new dye.
  • This process consists in starting with l-amino- 2- nitro-4-methylaminobenzene, transforming this by methylation into l-methylamino-2-nitro-4-methylaminobenzene, and subjecting the resulting product to hydroxyethylation, using a glycol halohydrin.
  • the amine function in position 1 is methylated by blocking the position of the hydrogen atom carried by the amine group in position 4with acetic anhydride, then blocking the position of one of the hydrogen atoms of the amine function in position 1 with paratoluene-sulfochloride, methylating the resulting product with a neutral methyl sulfate, and finally freeing the two previously blocked positions using first sulfuric acid to detach the tosyl group carried by the nitrogen atom in position 1, and then hydrochloric acid to detach the acetyl group carried by the nitrogen atom in position 4.
  • the nitro group is readily hydroxyethylated in the meta position with a commercially satisfactory yield, and without impurities.
  • a methyl group on one of the amine groups may be easily substituted on the initial product, after which a hydroxyethyl group is substituted on the other amino group, a product which will produce constant, reproducible, results is obtained, since there is no contamination by any secondary coloring agent.
  • the hair dyes comprising the composition according to the invention are simple aqueous solutions containing the composition, preferably having an alkaline pH. No oxidizing agent is required to develop the color.
  • Various additives known in the hair-coloring art may be included, such as organic solvents, thickening agents, detergents, and lacquers.
  • the time during which the hair-coloring solutions should be kept in contact with the hair varies within broad limits, but is preferably between 5 and 30 minutes.
  • the temperature of application may also be varied, but in most cases the dye is applied at room temperature.
  • the pH of these solutions is usually between 7 and 10 and preferably between 8 and 9.5.
  • alkaline products which may be used to adjust the pH are ammonia, any organic base, for example and alkylamine, an alkanolamine, or a heterocyclic amine.
  • concentration of the dye may be varied over a wide range, but this concentration is preferably between 0.l and 3 percent.
  • the dye according to the invention may be mixed with other dyes, whether nitrated, azo,
  • anthraquinone or of any other type conventionally used for dyeing hair.
  • EXAMPLE 2 1-methylamino-2-nitr0-4-(2'-hydroxy- This solution is applied to completely white hair. It is left for 15 to 20 minutes, after which the hair is rinsed, shampooed, and dried. A clear copperish chestnut shade is obtained.
  • composition for dyeing hair comprising an aqueous solution containing hair-dyeing amounts of the compound of claim 1.
  • a hair-dyeing composition as claimed in claim 2 having a pH between 8 and 9.5.
  • a hair-dyeing composition as claimed in claim 2 in which the concentration of said compound lies between 0.1 and 3 percent.
  • the method of dyeing human hair which comprises the step of applying thereto a composition containing dyeing amounts of 1-methylamino-2-nitro-4-(2'-hydroxyethyl)- methylaminobenzene.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)
US508578A 1964-11-19 1965-11-18 1-methylamino-2-nitro-4-(2{40 -hydroxyethyl)-methylaminobenzene for dyeing human hair Expired - Lifetime US3632292A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU47385A LU47385A1 (is") 1964-11-19 1964-11-19

Publications (1)

Publication Number Publication Date
US3632292A true US3632292A (en) 1972-01-04

Family

ID=19724034

Family Applications (1)

Application Number Title Priority Date Filing Date
US508578A Expired - Lifetime US3632292A (en) 1964-11-19 1965-11-18 1-methylamino-2-nitro-4-(2{40 -hydroxyethyl)-methylaminobenzene for dyeing human hair

Country Status (6)

Country Link
US (1) US3632292A (is")
BE (1) BE672400A (is")
DE (1) DE1569806C3 (is")
GB (1) GB1061515A (is")
LU (1) LU47385A1 (is")
NL (2) NL131840C (is")

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3619228A1 (de) * 1985-06-10 1986-12-11 L'oreal, Paris Faerbemittel fuer keratinfasern auf basis von halogenierten m-phenylendiaminen
US4637821A (en) * 1981-10-08 1987-01-20 L'oreal Tinctorial composition for keratin fibres, based on nitrated benzene dyestuffs

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2519251B1 (fr) * 1982-01-05 1985-11-22 Oreal Composition tinctoriales a base de precurseurs de colorants d'oxydation et d'orthonitranilines n-substituees comprenant une alcanolamine et du bisulfite de sodium et leur utilisation en teinture des fibres keratiniques
LU85098A1 (fr) * 1983-11-21 1985-07-17 Oreal Composition tinotoriale pour fibres keratiniques renfermant au moins une nitro-2 paraphenylenediamine n-substituee cosolubilisee et procedes de teinture de fibres keratiniques correspondants

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB190413956A (en) * 1904-06-20 1905-04-13 James Yate Johnson Improvements in the Manufacture and Production of Hydroxy-ethylaniline and of Derivatives thereof.
US2687431A (en) * 1950-12-20 1954-08-24 Gen Aniline & Film Corp Process of preparing nitro phenylenediamines
US2750327A (en) * 1953-06-01 1956-06-12 Lever Brothers Ltd Process of dyeing animal fibers and dyes and dyeing compositions therefor
US2750326A (en) * 1951-02-07 1956-06-12 Lever Brothers Ltd Process and composition for dyeing hair
US3168442A (en) * 1964-06-12 1965-02-02 Clairol Inc Compositions and methods of dyeing human hair with nitro-p-phenylenediamines

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB190413956A (en) * 1904-06-20 1905-04-13 James Yate Johnson Improvements in the Manufacture and Production of Hydroxy-ethylaniline and of Derivatives thereof.
US2687431A (en) * 1950-12-20 1954-08-24 Gen Aniline & Film Corp Process of preparing nitro phenylenediamines
US2750326A (en) * 1951-02-07 1956-06-12 Lever Brothers Ltd Process and composition for dyeing hair
US2750327A (en) * 1953-06-01 1956-06-12 Lever Brothers Ltd Process of dyeing animal fibers and dyes and dyeing compositions therefor
US3168442A (en) * 1964-06-12 1965-02-02 Clairol Inc Compositions and methods of dyeing human hair with nitro-p-phenylenediamines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Noller, Chemistry of Organic Compounds, 2nd Ed., W. B. Saunders Co., Philadelphia, Pa. (1957), pp. 478 479. *
Wagner et al., Synthetic Organic Chemistry, John Wiley & Sons, Inc., New York, (1953), pp. 572, 666 667, 678 and 679. *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4637821A (en) * 1981-10-08 1987-01-20 L'oreal Tinctorial composition for keratin fibres, based on nitrated benzene dyestuffs
DE3619228A1 (de) * 1985-06-10 1986-12-11 L'oreal, Paris Faerbemittel fuer keratinfasern auf basis von halogenierten m-phenylendiaminen
JPS61286313A (ja) * 1985-06-10 1986-12-16 ロレアル ケラチン繊維用染料組成物
GB2176212A (en) * 1985-06-10 1986-12-17 Oreal Dyeing compositions for keratinic fibres
US4725283A (en) * 1985-06-10 1988-02-16 L'oreal Dyeing compositions for keratinic fibres, based on halogenated meta-phenylenediamines
GB2176212B (en) * 1985-06-10 1989-07-05 Oreal Dyeing compositions for keratinic fibres

Also Published As

Publication number Publication date
DE1569806A1 (de) 1970-07-09
DE1569806B2 (de) 1974-11-14
NL131840C (is") 1971-06-16
NL7019082A (is") 1971-03-25
BE672400A (is") 1966-05-16
GB1061515A (en) 1967-03-15
DE1569806C3 (de) 1975-07-03
NL6514989A (is") 1966-05-20
LU47385A1 (is") 1966-05-20

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