WO1992013824A1 - 2,5-diaminophenoxy-oxaalcanes et leur utilisation comme precurseurs de colorants par oxydation - Google Patents

2,5-diaminophenoxy-oxaalcanes et leur utilisation comme precurseurs de colorants par oxydation Download PDF

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Publication number
WO1992013824A1
WO1992013824A1 PCT/EP1991/002453 EP9102453W WO9213824A1 WO 1992013824 A1 WO1992013824 A1 WO 1992013824A1 EP 9102453 W EP9102453 W EP 9102453W WO 9213824 A1 WO9213824 A1 WO 9213824A1
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WO
WIPO (PCT)
Prior art keywords
bis
formula
diaminophenoxy
oxaalkanes
hair
Prior art date
Application number
PCT/EP1991/002453
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German (de)
English (en)
Inventor
David Rose
Horst Höffkes
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 WO1992013824A1 publication Critical patent/WO1992013824A1/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
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Definitions

  • the invention relates to 2,5-diaminophenoxy-oxaalkanes, their preparation and use as oxidation dye precursors for the production of oxidation dyeings, in particular for the preparation of hair dyes.
  • Oxidation dyes contain oxidation dye precursors in a suitable carrier. Developments are used as oxidation dye precursors which form intensive colorations by oxidative coupling with one another or with one or more coupler substances in the presence of atmospheric oxygen or oxidizing agents.
  • z. B primary aromatic amines with a further in para or orthoposition free or substituted hydroxy ode A ino group, further diaminopyridines, heterocyclic hydrazone derivatives 4-aminopyrazolone derivatives and tetraaminopyrimidines.
  • the dyestuff which can be obtained by self-coupling of the developer substances is usually unsatisfactory. Coupling with phenols or aromatic amines can often be used to achieve high intensity and brilliant colors.
  • Suitable so-called coupler substances are, for example, -phenylenediamines, m-aminophenols for resorcinols, naphthol and pyrazolones.
  • oxidation hair dye precursors must first of all meet the following prerequisites: b they must develop the desired color shades with sufficient intensity in the oxidative coupling. You must also have a good ability to draw on human hair without staining the scalp too much. Au The color should be applied evenly, ie the more heavily used hair tips should not be colored more than the little damaged hairline. The dyeings thus produced must have a high stability against heat, light, shampoo and the chemicals used in the permanent waving. Finally, the oxidation hair dye precursors should be harmless from a toxicological and dermatological point of view.
  • the invention relates to bis (2,5-diaminophenoxy) oxaalkanes of the general formula I
  • n »2 or 3 and x is an integer from 1 to 3.
  • the compounds of formula I are new. However, they can be prepared in a conventional manner by adding a bis (2-amino-5-nitro-phenoxy) oxaalkane of the formula II , ,
  • n 2 or 3 and x is an integer from 1 to 3 is catalytically hydrogenated to the corresponding bis- (2,5-diamino-phenoxa) -oxaalkane of the formula I.
  • the hydrogenation is carried out by known processes using hydrogen in the presence of a catalyst, preferably from the group of platinum metals, e.g. B. in finely divided form or on activated carbon or in the presence of Raney nickel.
  • a catalyst preferably from the group of platinum metals, e.g. B. in finely divided form or on activated carbon or in the presence of Raney nickel.
  • the two nitro groups are converted into amino groups.
  • the new bis- (2,5-diaminophenoxy) oxaalkanes of the formula I or their water-soluble salts are suitable as developer compounds (primary intermediate) for producing oxidation colorations.
  • the oxidation stains that can be obtained from this apply particularly well to hair and other keratin fibers.
  • a particular advantage lies in the fact that the hair coloration obtained is applied evenly to damaged hair of different degrees and has a high resistance to shampoos. Even after repeated shampooing, the hair dyed according to the invention is evenly dyed.
  • the colors which can be produced by oxidation with the new bis- (2,5-diaminophenoxy) -oxaalkanes of the formula I can be modified considerably in terms of their intensity, brilliance and nuance by joint oxidation with numerous customary coupler compounds.
  • hair colorants which contain oxidation dye precursors in a carrier, the oxidation dye precursors being at least one bis- (2,5-diaminophenoxy) oxaalkane of formula I or its water-soluble salt as developer component and at least one in oxidation hair dye
  • Common coupler components are included.
  • those from the group of resorcinols, naphthols, aminophenols or hydroxypyridines are particularly suitable for the new developers of the formula (I).
  • hair dye of the type mentioned above which contains at least one compound from the group of resorcinols, naphthols, aminophenols or hydroxypyridines as a coupler component.
  • the bis (2,5-diaminophenoxy) oxaalkanes of the formula I form salts with acids.
  • the water-soluble salts which are formed with inorganic or organic acids, for. B. hydrochlorides, sulfates, phosphates, acetates, propionates, lactates or citrates.
  • the hair colorants according to the invention can also contain other known developer compounds if this is necessary to achieve certain shades.
  • known, direct hair dyes e.g. B. nitrophenylenediamine derivatives, anthraquinone dyes or indophenols can be added.
  • the new developers of the formula I and the known developer compounds which may additionally be present are generally used in approximately molar amounts, based on the coupler substances used. Even if the molar use has proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer substances and coupler substances can be contained in a molar ratio of 1: 0.5 to 1: 2.
  • the oxidation dye precursors are incorporated into a suitable cosmetic carrier.
  • suitable cosmetic carrier are e.g. B. creams, emulsions, gels or surfactant-containing, foaming solutions, eg. B. shampoos or other preparations, which are suitable for use on the hair.
  • Common components of such cosmetic preparations are e.g. B. wetting and emulsifying agents such as ' onic, nonionic, a pholytic or zwitterionic surfactants, e.g. B.
  • soaps fatty alcohol sulfates, alkane sulfonates, alpha-olefin sulfonates, fatty alcohol polyglycol ether sulfates, ethylene oxide addition products to fatty alcohols, to fatty acids and to alkylphenols, sorbitan fatty acid esters and fatty acid partial glycerides, fatty acid alkanolamides and thickeners such as, for. As methyl or hydroxyethylene cellulose, starch, fat components such as. B. fatty alcohols, paraffin oils or fatty acid esters, also perfume oils and hair care additives, such as. B. water-soluble cationic polymers, protein derivatives, pantothenic acid and cholesterol.
  • Particularly suitable as a carrier is a gel with a content of 1-20% by weight of a soap, preferably ammonium oleate or an oil-in-water emulsion with a content of 1-25% by weight of a fat component and 0, 5 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 0.2-5% by weight, preferably 1-3% by weight, of the total colorant.
  • the content of bis- (2,5-diaminonphenoxy) -oxaalkanes of the formula (I) in the hair colorants according to the invention can be about 0.05-10 millimoles per 100 g of the hair colorant.
  • the oxidative development of the color can basically be done with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a whitening effect on the hair is desired.
  • 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.
  • 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 of 6-10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can be in a range between 15 ° C and 40 ° C.
  • the hair dye is removed from the hair to be dyed 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 colorants according to the invention were produced in the form of a hair dyeing cre e-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 strands approx. 5 cm long, 90% gray, but not specially pretreated, and left there for 30 minutes at 27 ° C. After the dyeing process had ended, the hair was rinsed, washed out with a customary shampoo and then dried.
  • Example 1.1 (E1) and Example 1.2 (E2) were used as developer components.
  • the following compounds were used as coupler components
  • Example 2.19 the developer El was used instead of a coupler (thus a total of 15 mmol El).

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

Abstract

Des bis-(2,5-diaminophénoxy)-oxaalcanes ayant la formule (I), dans laquelle n vaut 2 ou 3 et x représente un nombre entier compris entre 1 et 3, sont utiles comme développeurs générateurs de colorations par oxydation, notamment pour produire des colorants pour cheveux. Avec des copulateurs appropriés, sélectionnés de préférence parmi les résorcines, les naphtols, les aminophénols ou les hydroxypyrines, on obtient des colorations très brillantes et uniformes des cheveux, avec de bonnes propriétés de résistance.
PCT/EP1991/002453 1991-01-31 1991-12-19 2,5-diaminophenoxy-oxaalcanes et leur utilisation comme precurseurs de colorants par oxydation WO1992013824A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914102907 DE4102907A1 (de) 1991-01-31 1991-01-31 2,5-diaminophenoxy-oxaalkane und deren verwendung als oxidationsfarbstoffvorprodukte
DEP4102907.0 1991-01-31

Publications (1)

Publication Number Publication Date
WO1992013824A1 true WO1992013824A1 (fr) 1992-08-20

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PCT/EP1991/002453 WO1992013824A1 (fr) 1991-01-31 1991-12-19 2,5-diaminophenoxy-oxaalcanes et leur utilisation comme precurseurs de colorants par oxydation

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Country Link
EP (1) EP0569368A1 (fr)
DE (1) DE4102907A1 (fr)
PL (1) PL296187A1 (fr)
WO (1) WO1992013824A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997031886A1 (fr) * 1996-02-29 1997-09-04 Henkel Kommanditgesellschaft Auf Aktien Derives d'aminophenol et leur utilisation dans des colorants d'oxydation pour les cheveux
FR2779948A1 (fr) * 1998-06-19 1999-12-24 Oreal Composition tinctoriale contenant du 1,8-bis- (2,5-diaminophenoxy)-3,5-dioxaoctane, une base d'oxydation additionnelle et un coupleur, et procedes de teinture
WO2007073562A2 (fr) * 2005-12-20 2007-06-28 Invitrogen Corporation Indicateurs d’ions fluorescents pour detection ionique de cadmium et de lanthanides
EP0966252B2 (fr) † 1997-09-01 2009-10-07 L'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

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2799960B1 (fr) * 1999-10-21 2002-12-20 Oreal Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
FR2799962B1 (fr) * 1999-10-21 2002-07-26 Oreal Compostion de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition
DE10125880A1 (de) * 2001-05-28 2002-12-05 Henkel Kgaa Neue Entwicklerkomponenten für Oxidationshaarfarben
DE10128472A1 (de) * 2001-06-12 2002-12-19 Henkel Kgaa Neue Kupplerkomponenten für Oxidationshaarfarben
DE10160815A1 (de) * 2001-12-11 2003-06-18 Henkel Kgaa Neue Oxidationsfarbstoffe mit 2,4-Dichlor-3-aminophenol
DE102004045323A1 (de) * 2004-09-16 2006-03-30 Henkel Kgaa Polyalkoxylierte Diaminobenzole als Entwickler

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011843A2 (fr) * 1978-12-02 1980-06-11 Henkel Kommanditgesellschaft auf Aktien Composants de développement pour colorants d'oxydation de cheveux, leur préparation et colorants pour cheveux les contenant
EP0036591A1 (fr) * 1980-03-22 1981-09-30 Henkel Kommanditgesellschaft auf Aktien Composants de coupleur pour colorants d'oxydation de cheveux, leur préparation et utilisation ainsi que colorants pour cheveux les contenant
DE3149330A1 (de) * 1981-12-12 1983-06-16 Henkel KGaA, 4000 Düsseldorf Hydroxyethylierte bis-(2,5-diaminophenoxy)-alkane und deren verwendung in haarfaerbemitteln
EP0358550A2 (fr) * 1988-09-06 1990-03-14 L'oreal Procédé de préparation d'alfa, omega-diamines aliphatiques, composés nouveaux et leur utilisation en teinture capillaire

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011843A2 (fr) * 1978-12-02 1980-06-11 Henkel Kommanditgesellschaft auf Aktien Composants de développement pour colorants d'oxydation de cheveux, leur préparation et colorants pour cheveux les contenant
EP0036591A1 (fr) * 1980-03-22 1981-09-30 Henkel Kommanditgesellschaft auf Aktien Composants de coupleur pour colorants d'oxydation de cheveux, leur préparation et utilisation ainsi que colorants pour cheveux les contenant
DE3149330A1 (de) * 1981-12-12 1983-06-16 Henkel KGaA, 4000 Düsseldorf Hydroxyethylierte bis-(2,5-diaminophenoxy)-alkane und deren verwendung in haarfaerbemitteln
EP0358550A2 (fr) * 1988-09-06 1990-03-14 L'oreal Procédé de préparation d'alfa, omega-diamines aliphatiques, composés nouveaux et leur utilisation en teinture capillaire

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 112, no. 17, 23. April 1990, Columbus, Ohio, US; abstract no. 158214P, V.M.DZIOMKO ET. AL.: 'Synthesis of coronands containing sulfonamide units in the macrocycle' Seite 716 ;Spalte 1 ; in der Anmeldung erwähnt *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997031886A1 (fr) * 1996-02-29 1997-09-04 Henkel Kommanditgesellschaft Auf Aktien Derives d'aminophenol et leur utilisation dans des colorants d'oxydation pour les cheveux
US6635241B1 (en) 1996-02-29 2003-10-21 Henkel Kommanditgesellschaft Auf Aktien Aminophenol derivatives and their use in oxidative hair dyes
EP0966252B2 (fr) † 1997-09-01 2009-10-07 L'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
FR2779948A1 (fr) * 1998-06-19 1999-12-24 Oreal Composition tinctoriale contenant du 1,8-bis- (2,5-diaminophenoxy)-3,5-dioxaoctane, une base d'oxydation additionnelle et un coupleur, et procedes de teinture
EP0966951A1 (fr) * 1998-06-19 1999-12-29 L'oreal Composition tinctoriale contenant du 1,8-bis(2,5-diaminophénoxy)-3,5-dioxaoctane, une base d'oxydation additionnelle et un coupleur, et procédés de teinture
WO2007073562A2 (fr) * 2005-12-20 2007-06-28 Invitrogen Corporation Indicateurs d’ions fluorescents pour detection ionique de cadmium et de lanthanides
WO2007073562A3 (fr) * 2005-12-20 2007-08-16 Invitrogen Corp Indicateurs d’ions fluorescents pour detection ionique de cadmium et de lanthanides
US8604243B2 (en) 2005-12-20 2013-12-10 Life Technologies Corporation Fluorescent ion indicators for cadmium and lanthanide ion detection

Also Published As

Publication number Publication date
PL296187A1 (en) 1994-01-10
DE4102907A1 (de) 1992-08-06
EP0569368A1 (fr) 1993-11-18

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