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WO1993016679A1 - DERIVES DE p-PHENYLENE DIAMINE UTILISES COMME PRODUITS INITIAUX DE COLORANTS D'OXYDATION - Google Patents

DERIVES DE p-PHENYLENE DIAMINE UTILISES COMME PRODUITS INITIAUX DE COLORANTS D'OXYDATION Download PDF

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Publication number
WO1993016679A1
WO1993016679A1 PCT/EP1993/000351 EP9300351W WO9316679A1 WO 1993016679 A1 WO1993016679 A1 WO 1993016679A1 EP 9300351 W EP9300351 W EP 9300351W WO 9316679 A1 WO9316679 A1 WO 9316679A1
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WO
WIPO (PCT)
Prior art keywords
formula
salts
hair
atom
oxidation
Prior art date
Application number
PCT/EP1993/000351
Other languages
German (de)
English (en)
Inventor
David Rose
Edgar Lieske
Horst Höffkes
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1993016679A1 publication Critical patent/WO1993016679A1/fr

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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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom

Definitions

  • the invention relates to the use of p-phenylenediamine derivatives as oxidation dye precursors, in particular as developer components in oxidation colorants for keratin fibers.
  • oxidation hair colorants play a preferred role for dyeing keratin fibers, in particular hair, furs and furs, because of their intensive colors and good fastness properties.
  • hair colorants contain oxidation dye precursors in an aqueous carrier.
  • Developer substances and coupler substances are used as oxidation dye precursors.
  • the developer components form the actual dyes under the influence of oxidizing agents or atmospheric oxygen with one another or under coupling with one or more coupler components.
  • developer substances Usually primary aromatic amines with a further free or substituted hydroxy or amino group in para or ortho position, furthermore diaminopyridine derivatives, heterocyclic hydrazone derivatives and 4-aminopyrazolone derivatives are used. Metaphenylene diamine derivatives, dihydroxynaphthalenes, naphthols, resorcinol derivatives, meta-aminophenols and pyrazolones are used as so-called coupler substances.
  • a certain developer substance can form very different color shades when combined with different couplers, but it is often not possible to achieve the multitude of natural hair color shades with the help of a single developer substance. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single natural-looking hair color. Therefore, there is a constant need for new developer components.
  • Good oxidation dye precursors must first of all meet the following requirements:
  • oxidation dye precursors p-Phenylenediamine and derivatives of this compound have long been known as oxidation dye precursors.
  • many of these compounds are toxicologically and dermatologically questionable because they have allergic properties. There is therefore a high level of interest in oxidation dye precursors which, on the one hand, form intensive colors with high fastness properties, but on the other hand are harmless from a toxicological and dermatological point of view.
  • German patent application DE 27 37 291 describes N- (2-alkoxyalkyl) -p-phenylenediamine derivatives, alkoxy being either methoxy or ethoxy and alkyl being either ethyl or propyl, as developer components in oxidation hair colorants.
  • the invention relates to the use of p-phenylenediamine derivatives of the formula I.
  • R ⁇ and R ⁇ independently of one another represent alkyl groups with 1 to 4 carbon atoms
  • X is a hydrogen atom or a halogen atom
  • n is a whole number between 2 and 4, or their salts as a precursor for producing oxidation colorations .
  • the p-phenylenediamine derivatives of the formula I are oxidation dye precursors of the developer substance type, ie they are able to form dyes under the action of oxidizing agents. However, particularly brilliant and intense colors are formed in the presence of coupler substances. Compounds such as, for example, are particularly suitable as coupler substances.
  • ⁇ -naphthol ortho-cresol, meta-cresol, 2,6-dimethylphenol, 2,5-dimethylphenol, pyrocatechol, pyrogallol, 1,5- or 1,7-dihydroxynaphthalene, 5-amino- 2-methylphenol, meta-aminophenol, 2,4-diaminoanisole, meta-toluenediamine, resorcinol, resorcinol monomethyl ether, meta-phenylene diamine in, l-phenyl-3- methyl-pyrazolone-5, l-Am ⁇ 'no-3-nitrobenzene, 2,4-dichloro-3-aminophenol, 1,3-B ⁇ s- (2,4-diaminophenoxy) propane, 2-Chlorresorc ⁇ n, 2-chloro- 6-methyl-3-aminophenol, 2,7-dihydroxynaphthalene, 2-methylresorc n, 2,4-diaminophenol.
  • the p-phenylenediamine derivatives of the formula I form a broad spectrum of color shades, of which those in the ruby to blue range are particularly noteworthy because of their good fastness properties.
  • the p-phenylenediamine derivatives of the formula I according to the invention are therefore eminently suitable for use as oxidation dye precursors of the developer type in hair colorants.
  • p-phenylenediamine derivatives of the formula I can either as such or in the form of their water-soluble salts with inorganic or organic
  • Acids e.g. B. as hydrochlorides, sulfates, phosphates, acetates, propionates, lactates or citrates.
  • methyl-2-methoxyethylamine (CH3-H- (CH2) 2-0CH3), which is known per se from the literature, is reacted with a nitrobenzene derivative of the formula II, where Y represents a fluorine atom, if X is a hydrogen atom or a fluorine atom and Y represents a chlorine atom when X is a chlorine atom and then converts the nitro group into the amino group in the reaction product of the formula III by catalytic hydrogenation.
  • Another object of the invention are hair dyes with a content of oxidation dye precursors in a cosmetic carrier, the oxidation dye precursors being p-phenylenediamine derivatives of the formula I, where R * and R ⁇ independently of one another are alkyl groups with 1 to 4 carbon atoms, X is a hydrogen atom or is a halogen atom and n is an integer from 2 to 4, or their salts as developer component in an amount of 0.05 to 10 mmol per 100 g of the hair dye and, if appropriate, conventional coupler components.
  • the developer substances and the coupler substances are generally used in equimolar amounts, but a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer substances and coupler substances can be used in a molar ratio of 1: 0.5 to 1: 2 .
  • the hair dye compositions according to the invention can also be known direct hair dyes, for. B. nitrophenylenediamine derivative, antrachinone dyes or indophenols can be added.
  • the oxidation dye precursors and optionally direct hair dyes are incorporated into an aqueous cosmetic carrier.
  • aqueous cosmetic carrier are e.g. B. creams, emulsions, gels or surfactant-containing foaming solutions z. B. shampoos or other preparations that are suitable for use on the hair.
  • Common components of such cosmetic preparations are e.g. B. wetting and emulsifying agents such as anionic, nonionic or ampholytic surfactants, e.g. B. fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, ethylene oxide addition products to fatty alcohols, fatty acids and alkylphenols, sorbitan fatty acid esters and fatty acid partial glycerides, fatty acid alkanolamides and thickeners, such as. As methyl or hydroxyethyl cellulose, starch, fatty alcohols, paraffin oils ,. Fatty acids, also perfume oils and hair care additives, such as. B. water-soluble cationic polymers, protein derivatives, pantothenic acid and cholesterol.
  • anionic, nonionic or ampholytic surfactants e.g. B. fatty alcohol sulfates, alkane
  • the constituents of the cosmetic carriers are used for the production of the hair colorants according to the invention in amounts customary for this purpose; z.
  • emulsifiers are used in concentrations of 0.5 to 30% by weight and thickeners in concentrations of 0.1 to 25% by weight of the total colorant.
  • Particularly suitable as a carrier is a gel with a content of 1 to 20% by weight of a soap, preferably ammonium oleate, or an oil-in-water emulsion with a content of 1 to 25% by weight of a fat component with 0.5 up to 30% by weight of an emulsifier from the group of anionic, nonionic, ampholytic or zwitterionic surfactants.
  • the oxidation dye precursors are mixed into the carrier in amounts of 0.2 to 5% by weight, preferably 1 to 3% by weight, of the total colorant.
  • the oxidative development of the coloring can in principle be carried out with atmospheric oxygen, but a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a brightening effect on the hair is desired.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a brightening effect on the hair is desired.
  • Particularly suitable oxidizing agents are hydrogen peroxide or its addition products with urea, melamine or sodium borate, as well as mixtures of such hydrogen peroxide addition products with potassium peroxide disulfate.
  • a preparation of the oxidizing agent is preferably mixed with the preparation of oxidation dye precursors and carrier immediately before hair coloring.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10.
  • the application temperatures can be in a range between 15 and 40 ° C.
  • the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. B. eim coloring shampoo was used.
  • Step 2 N-methyl-N- (2-methoxyethyl) -p-phenylenediamine dihydrochloride
  • step 1 The oil from step 1 was taken up in 200 ml of ethanol and in
  • Step 1 N-methyl-N- (2-methoxyethyl) -2-chloro-4-nitroaniline
  • Step 1 N-methyl-N- (2-methoxyethyl) -2-fluoro-4-nitroaniline
  • Stage 2 N-methyl-N- (2-methoxyethyl) ⁇ 2-fluoro-p-phenylenediamine dihydrochloride as in Example 1, stage 2,
  • Hair colorants according to the invention were produced in the form of a hair color cream emulsion of the following composition: Fatty alcohol C12-14 10.0 g
  • the constituents were mixed with one another in succession; after the developer components and the inhibitor had been added, the concentrated ammonia solution was first adjusted to pH 9.5 in the emulsion and then made up to 100 g with water.
  • the oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidation solution.
  • 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was applied to strands approx. 5 cm long, 90% gray, but not specially pretreated, and left there for 30 minutes at 27 ° C. After the dyeing process was completed, the hair was rinsed, washed with a conventional shampoo and then dried.
  • the developer components E1 to E3 according to the invention were used as developer components.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

Des dérivés de p-phénylène diamine de la formule générale (I) où R1 et R2 représentent indépendamment l'un de l'autre des groupes alkyle avec 1 à 4 atome de C, X représente un atome d'hydrogène ou un atome d'halogène et n est un nombre entier compris entre 2 et 4, ou leurs sels, constituent des produits initiaux de colorants d'oxydation intéressants qui se prêtent en tant que composants développeurs, conjointement avec les composants copulateurs habituels, à la formulation d'agents de coloration capillaire par oxydation, notamment pour obtenir des nuances dans la gamme allant du rubis au bleu.
PCT/EP1993/000351 1992-02-21 1993-02-13 DERIVES DE p-PHENYLENE DIAMINE UTILISES COMME PRODUITS INITIAUX DE COLORANTS D'OXYDATION WO1993016679A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924205329 DE4205329A1 (de) 1992-02-21 1992-02-21 P-phenylendiaminderivate als oxidationsfarbstoffvorprodukte
DEP4205329.3 1992-02-21

Publications (1)

Publication Number Publication Date
WO1993016679A1 true WO1993016679A1 (fr) 1993-09-02

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PCT/EP1993/000351 WO1993016679A1 (fr) 1992-02-21 1993-02-13 DERIVES DE p-PHENYLENE DIAMINE UTILISES COMME PRODUITS INITIAUX DE COLORANTS D'OXYDATION

Country Status (2)

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DE (1) DE4205329A1 (fr)
WO (1) WO1993016679A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007500245A (ja) * 2003-06-10 2007-01-11 スミスクライン ビーチャム コーポレーション 化合物
EP3727599B1 (fr) 2017-12-21 2023-03-22 Laboratoire Biosthetique Kosmetik GmbH&Co. KG Agent de coloration de fibres de kératine contenant une combinaison d'un dérivé de p-phénylène et de 2,7-naphthaline diol et son utilisation pour déduire la dominante jaune dans la chevelure

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4440955A1 (de) * 1994-11-17 1996-05-23 Henkel Kgaa Oxidationsfärbemittel
FR2767687B1 (fr) 1997-09-01 1999-10-01 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant du 2-chloro 6-methyl 3-aminophenol, une base d'oxydation et un coupleur additionnel, et procede de teinture
FR2767686B1 (fr) * 1997-09-01 2004-12-17 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant du 2-chloro 6-methyl 3-aminophenol et deux bases d'oxydation, et procede de teinture
FR2767685B1 (fr) * 1997-09-01 2004-12-17 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant du 2-chloro 6-methyl 3-aminophenol et une base d'oxydation, et procede de teinture
DE19847192A1 (de) 1998-10-13 2000-04-27 Wella Ag Mittel und Verfahren zur Färbung von Fasern

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2156527A1 (fr) * 1971-10-04 1973-06-01 Bristol Myers Co
FR2247202A1 (fr) * 1973-10-15 1975-05-09 Bristol Myers Co
US3970423A (en) * 1971-10-04 1976-07-20 Clairol Incorporated Oxidative hair dye compositions
DE2604804A1 (de) * 1975-02-10 1976-08-19 Konishiroku Photo Ind Fotografischer farbentwickler
FR2362112A1 (fr) * 1976-08-20 1978-03-17 Oreal Nouvelles paraphenylenediamines et compositions tinctoriales pour fibres keratiniques les contenant
DE2830497B1 (de) * 1978-07-12 1980-01-17 Schwarzkopf Gmbh Hans Verfahren zum Faerben von Humanhaar sowie Mittel zu seiner Durchfuehrung
EP0081790A1 (fr) * 1981-12-14 1983-06-22 Henkel Kommanditgesellschaft auf Aktien p-Phénylène diamines, leur préparation et usage
FR2626771A1 (fr) * 1988-02-08 1989-08-11 Oreal Composition de teinture des fibres keratiniques mettant en oeuvre un colorant indolique et au moins une paraphenylenediamine disubstituee sur l'un des groupements amino et procedes de mise en oeuvre

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2156527A1 (fr) * 1971-10-04 1973-06-01 Bristol Myers Co
US3970423A (en) * 1971-10-04 1976-07-20 Clairol Incorporated Oxidative hair dye compositions
FR2247202A1 (fr) * 1973-10-15 1975-05-09 Bristol Myers Co
DE2604804A1 (de) * 1975-02-10 1976-08-19 Konishiroku Photo Ind Fotografischer farbentwickler
FR2362112A1 (fr) * 1976-08-20 1978-03-17 Oreal Nouvelles paraphenylenediamines et compositions tinctoriales pour fibres keratiniques les contenant
DE2830497B1 (de) * 1978-07-12 1980-01-17 Schwarzkopf Gmbh Hans Verfahren zum Faerben von Humanhaar sowie Mittel zu seiner Durchfuehrung
EP0081790A1 (fr) * 1981-12-14 1983-06-22 Henkel Kommanditgesellschaft auf Aktien p-Phénylène diamines, leur préparation et usage
FR2626771A1 (fr) * 1988-02-08 1989-08-11 Oreal Composition de teinture des fibres keratiniques mettant en oeuvre un colorant indolique et au moins une paraphenylenediamine disubstituee sur l'un des groupements amino et procedes de mise en oeuvre

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RESEARCH DISLOSURE Bd. 147, Juli 1976, HAMPSHIRE Seiten 40 - 41 'Colour photographic developing composition' *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007500245A (ja) * 2003-06-10 2007-01-11 スミスクライン ビーチャム コーポレーション 化合物
EP3727599B1 (fr) 2017-12-21 2023-03-22 Laboratoire Biosthetique Kosmetik GmbH&Co. KG Agent de coloration de fibres de kératine contenant une combinaison d'un dérivé de p-phénylène et de 2,7-naphthaline diol et son utilisation pour déduire la dominante jaune dans la chevelure

Also Published As

Publication number Publication date
DE4205329A1 (de) 1993-08-26

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