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WO1991013881A1 - Derives de paraphenylene-diamine et utilisation desdits derives dans des teintures par oxydation - Google Patents

Derives de paraphenylene-diamine et utilisation desdits derives dans des teintures par oxydation Download PDF

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Publication number
WO1991013881A1
WO1991013881A1 PCT/EP1991/000409 EP9100409W WO9113881A1 WO 1991013881 A1 WO1991013881 A1 WO 1991013881A1 EP 9100409 W EP9100409 W EP 9100409W WO 9113881 A1 WO9113881 A1 WO 9113881A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
formula
hair
derivatives
developer
Prior art date
Application number
PCT/EP1991/000409
Other languages
German (de)
English (en)
Inventor
Günther KONRAD
Edgar Lieske
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 WO1991013881A1 publication Critical patent/WO1991013881A1/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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines

Definitions

  • the invention relates to new paraphenylenediamine derivatives, a process for their preparation and their use as oxidation dye precursors, in particular as developer components in oxidation hair colorants.
  • oxidation hair dyeing agents play a preferred role for dyeing hair because of their intense colors and good fastness properties.
  • hair colorants contain oxidation dye precursors in a cosmetic 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 of atmospheric oxygen with one another or under coupling with one or more coupler components.
  • Good oxidation dye precursors must first of all meet the following requirements: they have to develop the desired color shades with sufficient intensity and authenticity in the oxidative coupling. They must also have a good ability to draw on human hair, with no noticeable differences between damaged and freshly regrown hair. They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against permanent wave fluids. After all, they shouldn't stain the scalp too much and above all, they should be safe from a toxicological and dermatological point of view.
  • Primary aromatic amines with a further free or substituted hydroxyl or amino group located in para or ortho position, furthermore diaminopyridine derivatives, heterocyclic hydrazone derivatives and 4-aminopyrazolone derivatives are usually used as developer substances.
  • M-Phenylenediamine derivatives, naphthols, resorcinol derivatives and pyrazolones are used as so-called coupler substances.
  • oxidation dye precursors P-phenylenediamine and many derivatives of this compound have long been known as oxidation dye precursors.
  • many of these compounds are toxicologically and dermatologically questionable because they have utagenic and / or allergic properties.
  • oxidation dye precursors which, on the one hand, form intense colors with high fastness properties, but on the other hand are safe from a toxicological and dermatological point of view.
  • the compounds of the general formula (I) are new and are therefore themselves the subject of the present invention. They can be prepared by synthetic methods known per se from the literature by adding one mole of 4-nitro-N-aminoalkylaniline of the formula (II)
  • the new compounds of formula (I) or their salts are suitable for use as oxidation dye precursors of the developer type, in particular as developers in oxidation hair colorants. They are able to form dyes under the influence of oxidizing agents. However, particularly intense and brilliant dyes are formed by oxidative coupling in the presence of coupler substances.
  • paraphenylenediamine derivatives of the formula (I) according to the invention can be used either as such or in the form of their water-soluble salts with inorganic or organic acids, for.
  • Another object of the invention are hair dyes containing oxidation dye precursors in a cosmetic carrier, which as oxidation dye precursors 2- (4-amino-anilinoalkyl) -amino-4,6-diamino-l f 3,5-triazines.
  • coupler substances for the new developers of the formula (I) are especially those with phenolic hydroxyl groups, preferably phenols and resorcinols, or those of the 1,3-bis (2,4-diaminophenoxy) propane type are suitable.
  • Such hair dyes produce particularly brilliant colors in the range from blue to brown shades.
  • the developer substances and the coupler substances are generally used in equi-polar amounts, but a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer substances and coupler substances in a molar ratio of 1: 0.5 to 1 : 2 can be used.
  • the paraphenylene diamine derivatives according to the invention of the formula (I) or their salts can be used in an amount of 0.05 to 10 millimoles per 100 g of the hair dye. It is not necessary for the compounds of the formula (I) to be uniform compounds. Mixtures of such compounds can also be used.
  • the hair dye compositions according to the invention can also be known direct hair dyes, for. B. nitrophenylenediamine derivatives, anthraquinone dyes or indophenols can be added.
  • the oxidation dye precursors and any substantive dyes are incorporated into a suitable cosmetic carrier.
  • suitable cosmetic carriers are e.g. B. creams, emulsions, gels or surfactant-containing, foaming solutions, eg. 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, for example fatty alcohol sulfates, alkane sulfonates, alpha-olefin sulfonates, fatty alcohol polyglycol ether sulfates, ethylene oxide adducts with fatty alcohols, fatty acids and alkyl phthalates nols, sorbitan fatty acid esters and fatty acid partial glycerides, fatty acid alkanolamides and thickeners, such as.
  • anionic, nonionic or ampholytic surfactants for example fatty alcohol sulfates, alkane sulfonates, alpha-olefin sulfonates, fatty alcohol polyglycol ether sulfates, ethylene oxide adducts with fatty alcohols, fatty acids and alkyl phthalates nols, sorbitan fatty acid esters and fatty acid partial glycerides,
  • the constituents of the cosmetic carriers are used for the production of the hair colorants according to the invention in amounts customary for these purposes, for.
  • 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.
  • the oxidation dye precursors are mixed in the carrier in amounts of 0.2 to 5% by weight, preferably 1 to 3% by weight, of the total colorant.
  • Aminoanilinoalkyl) -amino-4,6-diamo, l, 3,5-triazines of the formula (I) are cream hair dye in the form of an oil-in-water emulsion with a content of
  • Alkali dithionite and ammonia in an amount to adjust the pH of the emulsion to a value between 8 and 10.
  • the alkyl sulfate or alkyl ether sulfate surfactant mentioned can be present as an alkali, ammonium or alkanolammonium salt with 2 or 3 carbon atoms in the alkanol group, e.g. B. as sodium, triethanol a monium or isopropanol moniu salt.
  • the alkyl (C ⁇ -C ⁇ s) ether sulfate surfactant a sulfuric acid monoester salt of an adduct of 1 to 10 moles of ethylene oxide with a Cifj-Ci ⁇ fatty alcohol can be used.
  • the oxidative development of the color can in principle be carried out with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially when a lightening effect on the hair is desired in addition to the coloring.
  • Particularly suitable oxidizing agents are hydrogen peroxide or its adducts with urea, melamine or sodium borate and mixtures of such hydrogen peroxide adducts with potassium peroxide disulfate.
  • the hair dye according to the invention can, regardless of the type of cosmetic preparation, for. B. as a cream, gel or shampoo, in a weakly acidic, neutral or alkaline environment.
  • the hair colorant in a pH range of 8 to 10.
  • the application temperatures is gron ⁇ nen in a range between 15 ° C and 40 lie ⁇ C.
  • the hair dye is removed from the hair to be colored by rinsing.
  • the hair is then washed with a mild shampoo and dried. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. B. a coloring shampoo was used.
  • Hair dyes according to the invention were produced in the form of a hair dyeing cream emulsion of the following composition:
  • the ingredients were mixed together in order. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to 9.5 with concentrated ammonia solution, and the mixture was then made up to 100 g with water.
  • the oxidative development of the color was carried out using 3% hydrogen peroxide solution as the oxidizing agent.
  • 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was applied to approx. 5 cm long strands of standardized, 90% gray, but not particularly pretreated human hair and left there at 27 ° C. for 30 minutes. After the dyeing process had ended, the hair was rinsed, washed out with a customary shampoo and then dried.
  • the following compounds were used as couplers:

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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

Nouveaux dérivés de paraphénylène-diamine de la formule générale (I) dans laquelle R1 et R2 sont de l'hydrogène, des groupes alkyles avec 1 à 4 atomes de carbone, des groupes hydroxyalkyle avec 2 à 4 atomes de carbone ou des groupes alkoxyalkyle avec 1 à 4 atomes de carbone dans le groupe alkoxy et 2 à 4 atomes de carbone dans le groupe alkyle et n est un nombre de 2 à 4, ainsi que leurs sels, qui constituent des produits préliminaires utiles pour les teintures par oxydation. Lesdits produits peuvent être utilisés en tant qu'ingrédients de développement, avec les ingrédients copulateurs habituels, afin de formuler des teintures par oxydation pour les cheveux, en particulier pour produire des nuances bleues à brunes.
PCT/EP1991/000409 1990-03-14 1991-03-05 Derives de paraphenylene-diamine et utilisation desdits derives dans des teintures par oxydation WO1991013881A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4008049.8 1990-03-14
DE19904008049 DE4008049A1 (de) 1990-03-14 1990-03-14 Paraphenylendiamin-derivate und deren verwendung in oxidationsfaerbemitteln

Publications (1)

Publication Number Publication Date
WO1991013881A1 true WO1991013881A1 (fr) 1991-09-19

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/000409 WO1991013881A1 (fr) 1990-03-14 1991-03-05 Derives de paraphenylene-diamine et utilisation desdits derives dans des teintures par oxydation

Country Status (2)

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DE (1) DE4008049A1 (fr)
WO (1) WO1991013881A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998001434A1 (fr) * 1996-07-03 1998-01-15 Hans Schwarzkopf Gmbh & Co. Kg Nouveaux derives de la piperazine et teintures d'oxydation
US6165230A (en) * 1997-02-26 2000-12-26 Henkel Kommanditgesellschaft Auf Aktien 1,4-diazacycloheptane derivatives and their use in hair oxidation dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10101206A1 (de) * 2001-01-11 2002-07-18 Henkel Kgaa Entwickler/Entwickler-Hybridfarbstoffe und hybridfarbstoffvorprodukte

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1519518A1 (de) * 1964-08-05 1970-01-15 Unilever Nv Verfahren zum Faerben von Keratinmaterial
DE2613707A1 (de) * 1976-03-31 1977-10-13 Henkel & Cie Gmbh Haarfaerbemittel
DE3510039A1 (de) * 1985-03-20 1986-09-25 Henkel KGaA, 4000 Düsseldorf Haarfaerbemittel
WO1990001022A2 (fr) * 1988-07-18 1990-02-08 Henkel Kommanditgesellschaft Auf Aktien 3,5-dimanophenyl-alkylamines et leur utilisation en tant que colorants pour cheveux

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1519518A1 (de) * 1964-08-05 1970-01-15 Unilever Nv Verfahren zum Faerben von Keratinmaterial
DE2613707A1 (de) * 1976-03-31 1977-10-13 Henkel & Cie Gmbh Haarfaerbemittel
DE3510039A1 (de) * 1985-03-20 1986-09-25 Henkel KGaA, 4000 Düsseldorf Haarfaerbemittel
WO1990001022A2 (fr) * 1988-07-18 1990-02-08 Henkel Kommanditgesellschaft Auf Aktien 3,5-dimanophenyl-alkylamines et leur utilisation en tant que colorants pour cheveux

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998001434A1 (fr) * 1996-07-03 1998-01-15 Hans Schwarzkopf Gmbh & Co. Kg Nouveaux derives de la piperazine et teintures d'oxydation
US6165230A (en) * 1997-02-26 2000-12-26 Henkel Kommanditgesellschaft Auf Aktien 1,4-diazacycloheptane derivatives and their use in hair oxidation dyes

Also Published As

Publication number Publication date
DE4008049A1 (de) 1991-09-19

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