DE2334738A1 - Hair-dyestuff for oxidation-dyeing process - contg. 4-hydroxy-quinolone-2-derivs as coupling components - Google Patents

Hair-dyestuff for oxidation-dyeing process - contg. 4-hydroxy-quinolone-2-derivs as coupling components

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Publication number
DE2334738A1
DE2334738A1 DE19732334738 DE2334738A DE2334738A1 DE 2334738 A1 DE2334738 A1 DE 2334738A1 DE 19732334738 DE19732334738 DE 19732334738 DE 2334738 A DE2334738 A DE 2334738A DE 2334738 A1 DE2334738 A1 DE 2334738A1
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Germany
Prior art keywords
hydroxy
quinolone
hair
gray
dyestuff
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.)
Pending
Application number
DE19732334738
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German (de)
Inventor
Ferdi Dipl-Chem Dr Saygin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to DE19732334738 priority Critical patent/DE2334738A1/en
Publication of DE2334738A1 publication Critical patent/DE2334738A1/en
Pending legal-status Critical Current

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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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • 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

Abstract

Hair-dyestuff compsn. for the oxidation-dyeing process contains as a coupling component a deriv. of 4-hydroxy-quinolone-2 having the formula (I) (in which R is H or a 1-4C alkyl; R' is H, a 1-4C alkyl; a halogen atom, OH, lower alkoxy gp., beta-hydroxyethyl or a dialkylamino gp. contg. 1-4C alkyls). The dyestuff is applied in the form of a soln., emulsion, cream or gel, wt. 15-40 degrees C. Alkaline reaction is pref. Intensive colouration in various shades is obtained; the exhaustion is very good; fast colours are produced; they may be eliminated by means of a reducing agent. The colour range is from pale blonde to dark brown, and from green to blue and violet.

Description

Gegenstand der Erfindung sind Mittel zur oxidativen Färbung von Haaren auf Basis von 4-Hydroxy-chinolon-2-derivaten als Kupplerkomponente.The invention relates to agents for the oxidative coloring of hair based on 4-hydroxy-quinolone-2-derivatives as Coupler component.

Für das Färben von Haaren spielen die sogenannten Oxidationsfarben, die durch oxidative Kupplung einer Entwicklerkomponente mit einer Kupplerkomponente entstehen, wegen ihrer intensiven Farben und sehr guten Echtheitseigenschaften eine bevorzugte Rolle. Als Entwicklersubstanzen werden üblicherweise Stickstoffbasen wie p-Phenylendiaminderivate, Diaminopyridine, 4-Amino-pyrazolon-derivate, heterocyclische Hydrazone eingesetzt. Als sogenannte Kupplerkomponenten werden m-Phenylen-diaminderivate, Phenole, Naphthole, Resorcinderivate und Pyrazolone genannt.The so-called oxidation colors, which are produced by the oxidative coupling of a developer component, play a role in the coloring of hair with a coupler component arise because of their intense colors and very good fastness properties preferred role. Nitrogen bases such as p-phenylenediamine derivatives, diaminopyridines, 4-amino-pyrazolone derivatives, heterocyclic hydrazones used. So-called coupler components are m-phenylene-diamine derivatives, phenols, naphthols, resorcinol derivatives and called pyrazolones.

Gute Oxidationshaarfarbstoffkomponenten müssen in erster Linie folgende Voraussetzungen erfüllen:Good oxidation hair dye components must primarily meet the following requirements:

Sie müssen bei der oxidativen Kupplung mit den jeweiligen Entwickler- beziehungsweise Kupplerkomponenten die gewünschten Farbnuancen in ausreichender Intensität ausbilden. Sie müssen ferner ein ausreichendes bis sehr gutes Aufziehvermögen auf menschlichem Haar besitzen.In the oxidative coupling with the respective developer or coupler components, you must have the desired Develop color nuances with sufficient intensity. You must also have a sufficient to very good absorption capacity own human hair.

409885/1343409885/1343

Henkel & CIe GmbHHenkel & CIe GmbH

xur Palantanmtldung Dxur palant declaration D

47144714

Es besteht daher bei der Suche nach brauchbaren Oxidationshaarfarbstoffen die Aufgabe, geeignete Komponenten aufzufinden, die vorstehende Voraussetzungen in optimaler Weise erfüllen.There is therefore a search for useful oxidation hair dyes the task of finding suitable components that meet the above requirements in an optimal way fulfill.

Diese Aufgabe wurde dadurch gelöst, daß man als Kupplerkomponente 4-Hydroxy-chinolon-2-derivate der allgemeinen FormelThis object was achieved by using 4-hydroxy-quinolone-2-derivatives of the general as the coupler component formula

OHOH

in der R Wasserstoff oder einen gerad- oder verzweigtkettigen Alkylrest mit 1-4 Kohlenstoffatomen, R'Wasserstoff, einen gerad- oder verzweigtkettigen Alkylrest mit 1-4 Kohlenstoffatomen, ein Halogenatom, eine Hydroxylgruppe, eine niedere Alkoxygruppe, eine ß-Hydroxyäthylgruppe oder eine Dialkylaminogruppe mit Alkylresten mit 1-4 Kohlenstoffatomen bedeuten, verwendet.in which R is hydrogen or a straight or branched chain Alkyl radical with 1-4 carbon atoms, R'hydrogen, a straight or branched chain alkyl radical with 1-4 carbon atoms, a halogen atom, a hydroxyl group, a lower one Alkoxy group, a ß-hydroxyethyl group or a dialkylamino group with alkyl radicals with 1-4 carbon atoms are used.

Bei ihrem Einsatz als Kupplungskomponenten liefern die erfindungsgemäßen Verbindungen mit den verschiedenen Entwicklerkomponenten die unterschiedlichsten Farbnuancen und stellen eine wesentliche Bereicherung der oxidatlven Haarfärbemöglichkeiten dar.When used as coupling components, the inventive Connections with the various developer components the most varied of color nuances and represent an essential enrichment of the oxidative hair coloring possibilities.

Als Beispiele für erfindungsgemäß.zu verwendende Kupplerkomponenten sind 7-Dimethylamino-4-hydroxy-chinolon-2, 6-Methyl-4-hydroxy-chinolon-2f 6-Dimethylamino-4-hydroxychinolon-2, o-Methoxy^-hydroxy-chinolon^, 8-chlor-4-hydroxychinolon-2, l-Methyl-7-dimethylamino-4-hydroxy-chinolon-2,As examples of erfindungsgemäß.zu used intermediates are 7-dimethylamino-4-hydroxyquinolone-2, 6-methyl-4-hydroxyquinolone-2 f 6-dimethylamino-4-hydroxyquinolone-2, o-methoxy ^ -hydroxy- quinolone ^, 8-chloro-4-hydroxyquinolone-2, l-methyl-7-dimethylamino-4-hydroxy-quinolone-2,

409885/13 43409885/13 43

■- 3 -■ - 3 -

Henkel & Cie GmbH Μ* J zur Pal.nt«inn>.ld»n| D *♦ f J-1 Henkel & Cie GmbH Μ * J zur Pal.nt «inn> .ld» n | D * ♦ f J-1

l-Methyl-4-hydroxy-chinolon-2, l-Methyl-S-chlor^-hydroxychinolon-2, l^-Dimethyl^-hydroxy-chinolon^, 1-Methyl-6-dimethylamino-4-hydroxy-chinolon-2, 6-(2-Hydroxyäthyl)-4-hydroxy-chinolon-2, l-i-Propyl-4-hydroxy-chinolon-2, l-Methyl-7-i-propyl-4-hydroxy-chinolon-2, l-n-Butyl-8-brom-4-hydroxy-chinolon-2 zu nennen.l-methyl-4-hydroxy-quinolone-2, l-methyl-S-chloro ^ -hydroxyquinolone-2, l ^ -Dimethyl ^ -hydroxy-quinolone ^, 1-methyl-6-dimethylamino-4-hydroxy-quinolone-2, 6- (2-hydroxyethyl) -4-hydroxy-quinolone-2, l-i-propyl-4-hydroxy-quinolone-2, 1-methyl-7-i-propyl-4-hydroxy-quinolone-2, 1-n-butyl-8-bromo-4-hydroxy-quinolone-2 to call.

Die erfindungsgemäß als Kupplerkomponenten einzusetzenden 4-Hydroxy-chinolon-2-derivate stellen literaturbekannte Verbindungen dar und lassen sich nach Verfahren herstellen, wie sie von Harnisch und Brack in Liebigs Annalen der Chemie 740, 164- ff. (1970), sowie von Lamberton und Price in Australian Journal of Chemistry 6, 173 ff (1953) beschrieben sind.The 4-hydroxyquinolone-2-derivatives to be used according to the invention as coupler components are known from the literature Compounds represent and can be produced by processes as described by Harnisch and Brack in Liebig's Annalen der Chemie 740, 164ff. (1970), and by Lamberton and Price in Australian Journal of Chemistry 6, 173 ff (1953) are.

Als weitere Färbstoffkomponente werden in den erfindungsgemäßen Haarfärbemitteln die üblicherweise als Entwickler- · substanzen eingesetzten Verbindungen verwendet. Zu diesen sind primäre aromatische Amine mit einer weiteren in p-Stellung befindlichen funktionellen Gruppe zu zählen, wie z.B. p-Phenylendiamin, p-Toluylendiamin, p-Dimethylamino-anilin, p-Aminophenol, p-Diaminoanisol bzw. andere Verbindungen der genannten Art, die weiterhin eine oder mehrere funktioneile Gruppen wie OH-, NH2-, NHR-, NRg-Gruppe, wobei R einen niederen Alkyl- oder Hydroxylalkylrest mit 1-4 Kohlenstoffatomen darstellt, enthalten. Weitere geeignete Entwicklersubstanzen stellen die Diaminopyridinderivate, heterocyclische Hydrazonderivate und 4-Amino-pyrazolonderivate, wie sie in der österreichischen Patentschrift 277 4-65 beschrieben sind, dar.The compounds customarily used as developer substances are used as further dye components in the hair colorants according to the invention. These include primary aromatic amines with a further functional group in the p-position, such as p-phenylenediamine, p-tolylenediamine, p-dimethylamino-aniline, p-aminophenol, p-diaminoanisole or other compounds of the type mentioned, which also contain one or more functional groups such as OH, NH 2 , NHR, NRg groups, where R represents a lower alkyl or hydroxylalkyl radical having 1-4 carbon atoms. Other suitable developer substances are the diaminopyridine derivatives, heterocyclic hydrazone derivatives and 4-amino-pyrazolone derivatives, as described in Austrian patent specification 277 4-65.

In den erfindungsgemäßen Haarfärbemitteln werden die Kupplerkomponenten im allgemeinen in etwa molaren Mengen, bezogen auf die verwendeten Entwicklersubstanzen, eingesetzt. Wenn sich auch der molare Einsatz als zweckmäßig erweist, so ist es jedoch nicht nachteilig, wenn die Kupplerkomponente in einem gewissen Überschuß oder Unterschuß zum Einsatz gelangt.The coupler components are used in the hair colorants according to the invention generally used in approximately molar amounts, based on the developer substances used. if If the molar use proves to be expedient, however, it is not disadvantageous if the coupler component in a certain excess or deficit is used.

409885/1343409885/1343

Henkel & CIe GmbH s*. 4 «rf.^t.-«.id.n,dHenkel & CIe GmbH s *. 4 «rf. ^ T .-«. Id.n, d

Es ist ferner nicht erforderlich, daß die Kupplersubstanz und die Entwicklersubstanz einheitliche Produkte darstellen, vielmehr können sowohl die Kupplersubstanz Gemische der erfindungsgemäßen 4-Hydroxy-chinolen-2-derivate als auch die Entwicklersubstanz Gemische der vorstehend genannten Entwicklerkomponenten darstellen.Furthermore, it is not necessary that the coupler substance and the developer substance represent uniform products, rather, both the coupler substance mixtures of the 4-hydroxy-quinolene-2 derivatives according to the invention as well the developer substance represent mixtures of the aforementioned developer components.

Die oxidative Kupplung, d.h. die Entwicklung der Färbung, kann grundsätzlich wie bei anderen Oxidationshaarfarbstoffen auch, durch Luftsauerstoff erfolgen. Zweckmäßlgerweise werden jedoch chemische Oxidationsmittel eingesetzt. Als solche kommen insbesondere Wasserstoffperoxid oder dessen Anlagerungsprodukte an Harnstoff, Melamin und Natriumborat sowie Gemische aus derartigen Wasserstoffperoxidanlagerungsverbindungen mit Kaliumperoxidisulfat in Betracht.The oxidative coupling, i.e. the development of the color, can basically be the same as with other oxidation hair dyes also, done by atmospheric oxygen. However, chemical oxidizing agents are expediently used. In particular, hydrogen peroxide or its addition products with urea, melamine and sodium borate are used as such and mixtures of such hydrogen peroxide addition compounds with potassium peroxydisulfate are possible.

Die erfindungsgemäßen Haarfärbemittel werden für den Einsatz in entsprechende kosmetische Zubereitungen wie Cremes, Emulsionen, Gele oder auch einfache Lösungen eingearbeitet und unmittelbar vor der Anwendung auf dem Haar mit einem der genannten Oxidationsmittel versetzt. Die Konzentration derartiger färberischer Zubereitungen an Kuppler-Entwicklerkombination beträgt 0,2 bis 5 Gewichtsprozent, vorzugsweise 1-3 Gewichtsprozent. Zur Herstellung von Cremes, Emulsionen oder Gelen werden die Farbstoffkomponenten mit den für derartige Präparationen üblichen weiteren Bestandteilen gemischt. Als solche zusätzlichen Bestandteile sind z.B. Netzoder Emulgiermittel vom anionischen oder nichtionogenen Typ wie Alkylbenzolsulfonate, Fett-, Alkoholsulfate, Alkylsulfonate, Fettsäurealkanolamide, Anlagerungsprodukte von Äthylenoxid an Fettalkohole, Verdickungsmittel wie Methylcellulose, Stärke, höhere Fettalkohole, Paraffinöl, Fettsäuren, ferner Parfümöle und Haarpflegemittel wie Pantothensäure und CholesterinThe hair dyes according to the invention are used in corresponding cosmetic preparations such as creams, Emulsions, gels or even simple solutions incorporated and immediately before application on the hair with a the said oxidizing agents added. The concentration of such dyeing preparations in coupler-developer combinations is 0.2 to 5 percent by weight, preferably 1-3 percent by weight. For the production of creams, emulsions or gels, the dye components are mixed with the other ingredients customary for such preparations. Such additional ingredients are, for example, wetting agents or emulsifying agents of the anionic or nonionic type such as alkylbenzenesulfonates, fatty and alcohol sulfates, alkylsulfonates, Fatty acid alkanolamides, addition products of ethylene oxide with fatty alcohols, thickeners such as methyl cellulose, starch, higher fatty alcohols, paraffin oil, fatty acids, and also perfume oils and hair products such as pantothenic acid and cholesterol

409885/1343 " 5 409885/1343 " 5th

Henkel & Cie GmbH μ ^ «rraimanm.idum ο 4714Henkel & Cie GmbH μ ^ «rraimanm.idum ο 4714

zu nennen. Die genannten Zusatzstoffe werden dabei in den für diese Zwecke üblichen Mengen eingesetzt, wie.z.B. Metz- und Emulgiermittel in Konzentrationen von 0,5-30 Gewichtsprozent und Verdickungsmittel in Konzentrationen von 0,1 - 25 Gewichtsprozent, jeweils bezogen auf die gesamte Zubereitung.to call. The additives mentioned are used in the amounts customary for these purposes, such as e.g. Butchering and emulsifying agents in concentrations of 0.5-30 Percentage by weight and thickener in concentrations of 0.1-25 percent by weight, each based on the total Preparation.

Die Anwendung der erfindungsgemäßen Haarfärbemittel kann, unabhängig davon, ob es sich um eine Lösung, eine Emulsion, eine Creme oder ein Gel handelt, im schwach sauren, neutralen oder insbesondere alkalischen Milieu erfolgen. Die Anwendungstemperaturen bewegen sich dabei im Bereich von 15 bis 40°C. Nach einer Einwirkungsdauer von ca. J50 Minuten wird das Haarfärbemittel vom zu färbenden Haar durch Spülen entfernt. Hernach wird das Haar mit einem milden Shampoo nachgewaschen und getrocknet.The hair dye according to the invention can be used, regardless of whether it is a solution, an emulsion, a cream or gel is done in a weakly acidic, neutral or, in particular, alkaline medium. The application temperatures are in the range from 15 to 40 ° C. After an exposure time of about J50 minutes, the hair dye becomes removed from the hair to be colored by rinsing. Then the hair is washed with a mild shampoo and dried.

Die mit den erfindungsgemäßen Haarfärbemitteln erzielbaren Farbtöne zeigen unter Einsatz unterschiedlicher Kuppler- und Entwicklerkomponenten eine außerordentliche Variationsmöglichkeit, die von hellblond bis dunkelbraun und grün über blau bis violett reicht. Die erzielten Färbungen haben gute Licht-, Wasch- und Reibechtheitseigenschaften und lassen sich leicht mit Reduktionsmitteln wieder abziehen.The hues that can be achieved with the hair colorants according to the invention show when using different couplers and Developer components an extraordinary possibility of variation, from light blonde to dark brown and green to blue until purple reaches. The dyeings obtained have good light, wash and rub fastness properties and are easy to use remove again with reducing agents.

Die nachfolgenden. Beispiele sollen den Erfindungsgegenstand näher erläutern ohne ihn jedoch hierauf zu beschränken.The following. Examples are intended to explain the subject matter of the invention in greater detail without, however, restricting it thereto.

409885/1343409885/1343

Henkel A Cie GmbHHenkel A Cie GmbH

xur Pot«ntanm«Idung Oxur Pot "ntanm" Idung O

47144714

BeispieleExamples

Die erfindungsgemäßen Haarfärbemittel wurden in Form einer Cremeemulsion eingesetzt. Dabei wurden in eine Emulsion ausThe hair colorants according to the invention were used in the form of a cream emulsion. In a Emulsion

10 Gew.-Teilen Fettalkoholen der Kettenlänge C12-C1Q10 parts by weight of fatty alcohols of chain length C 12 -C 1 Q

10 Gew.-Teilen Fettalkoholsulfat (Natriumsalz) Kettenlänge cip~Cl810 parts by weight of fatty alcohol sulfate (sodium salt) chain length c ip ~ C l8

75 Gew.-Teilen Wasser75 parts by weight of water

jeweils 0,01 Mol der in nachstehender Tabelle aufgeführten Kuppler- und Entwicklersubstanzen eingearbeitet. Danach wurde der pH-Wert der Emulsion mittels Ammoniak auf 9*5 eingestellt und die Emulsion mit Wasser auf 100 Gew.-Teile aufgefüllt. Die oxidative Kupplung wurde mit 1 #iger Wasserstoffperoxidlösung durchgeführt, wobei die Entwicklungszeit 30 Minuten betrug. Die in der Tabelle verzeichneten Färbeergebnisse wurden auf zu 80 % ergrautem menschlichem Haar erzielt.in each case 0.01 mol of the coupler and developer substances listed in the table below are incorporated. The pH of the emulsion was then adjusted to 9 * 5 by means of ammonia and the emulsion was made up to 100 parts by weight with water. The oxidative coupling was carried out with 1 # hydrogen peroxide solution, the development time being 30 minutes. The coloring results recorded in the table were achieved on 80 % gray human hair.

Tabelle 1 Table 1

Beispiel
Nr. example
No.

Entwicklerdeveloper

KupplerCoupler

Farbtonhue

4-Amino-jJ-carbonamido-1-phenylpyrazolon-5 4-Amino-jJ-carbonamido-1-phenylpyrazolone-5

7-Dimethylamino- blaugrau 4-hydroxy-chinolon-2 7-dimethylamino blue-gray 4- hydroxy-quinolone-2

1-Me thy 1-7-dime thy 1-1-Me thy 1-7-dime thy 1-

amlno-4-hydroxy- dunkel-amlno-4-hydroxy- dark-

chinolon-2 blauquinolone-2 blue

1-Methy1-4-hydroxy- violett-1-methy1-4-hydroxy- violet-

chinolon-2 ' grau 409885/1343 quinolone-2 'gray 409885/1343

Henkel & CIe GmbHHenkel & CIe GmbH

*7 lur Pol«nlanm«!dun» D if "J ]_ i\ * 7 lur Pol «nlanm«! Dun »D if " J] _ i \

Beispiel
Nr.example
No. Entwicklerdeveloper KupplerCoupler Farbtonhue grau-
magentaGray-
magenta 44th 4-Amino-3-carbon-
amido-1-phenyl-
pyrazolon-54-amino-3-carbon
amido-1-phenyl-
pyrazolone-5 8-chlor-4-hydroxy-
chinolon-28-chloro-4-hydroxy
quinolone-2 birken
graubirch trees
Gray grau-
violettGray-
violet 55 IlIl 6-Methyl-4-hydroxy-
chinolon-26-methyl-4-hydroxy
quinolone-2 rotgraured-gray grau-
violettGray-
violet 66th IlIl 6-Methoxy-4hydroxy-
chinolon-26-methoxy-4hydroxy
quinolone-2 graubraungray-brown 77th ttdd l-Methyl-6-dimethyl-
amino-4-hydroxy-
chinolon-2l-methyl-6-dimethyl-
amino-4-hydroxy
quinolone-2 rotbraunred-brown 88th titi l,6-Dimethyl-4-hy-
droxy-chinolon-21,6-dimethyl-4-hy-
droxy-quinolone-2 grauviolettgray-violet 9
109
10 4-Amino-3-äthoxy-
carbonyl-1-phenyl-
pyra.zolon-5
ti4-amino-3-ethoxy
carbonyl-1-phenyl-
pyra.zolon-5
ti 7-Dimethylamino-4-
hydroxychinolon-2 grauviolett
1-Methy1-7-dimethyl- grau-
amino-4-hydroxy-chinolon-2 violett7-dimethylamino-4-
hydroxyquinolone-2 gray-violet
1-Methy1-7-dimethyl- gray-
amino-4-hydroxy-quinolone-2 purple 1111 IlIl 1-Methyl-4-hydroxy-
chinolon-21-methyl-4-hydroxy
quinolone-2 1212th ttdd 8-Chlor-4-hydroxy-
chinolon-28-chloro-4-hydroxy
quinolone-2 1313th IlIl 6-Methy1-4-hydroxy-
chinolon-26-methy1-4-hydroxy-
quinolone-2

1,6-Dimethy1-4-hydroxy- rotchinolon-2 violett 1,6- Dimethy1-4-hydroxy-redquinolone-2 violet

ρ-Toluylendiaminρ-tolylenediamine

7-Dimethylamino-4-hydroxy - chinolon-27-dimethylamino-4-hydroxy - quinolone-2

l-Methyl-7-dimethylamino-4-hydroxychinolon-2 1-methyl-7-dimethylamino-4-hydroxyquinolone-2

1-Methy1-4-hydroxychinolon-2 1-Methy1-4-hydroxyquinolone-2

8-chlor-4-hydroxychinolon-2 8-chloro-4-hydroxyquinolone-2

6-Methyl-4-hydroxychinolon-2 6-methyl-4-hydroxyquinolone-2

A09885/13A3 *A09885 / 13A3 *

dunkles graublaudark gray blue

dunkles braungraudark brown gray

graubraungray-brown

dunkelbraun dark brown

gelbbraunyellow-brown

Henkelhandle & Cio GmbH %^e 8& Cio GmbH % ^ e 8 p-Toluylendiaminp-tolylenediamine ηη 2334738
Ilt ι h.
xur Pot*ntonm*ldung O r [ L *T 2334738
Ilt ι h.
xur Pot * ntonm * ldung O r [L * T Farbtonhue dunkel
graudark
Gray Beispiel Entwickler
Nr.Example developer
No. ti
Itti
It IlIl KupplerCoupler kaffee
brauncoffee
Brown nickel
grünnickel
green 2020th 2,5-Diaminoanisol2,5 diamino anisole IlIl b-Me thoxy-4-hydroxy-
chinolon-2b-methoxy-4-hydroxy-
quinolone-2 l-Methyl-6-dimethyl-
amino-4-hydroxy- dunkel-
chinolon-2 braun
1,6-Dimethy1-4-hydroxy- rot-
chinolon-2 braunl-methyl-6-dimethyl-
amino-4-hydroxy dark
quinolone-2 brown
1,6-Dimethy1-4-hydroxy- red-
quinolone-2 brown dunkel-
graudark-
Gray 21
2221
22nd IlIl IlIl 7-Dimethylamino-4-
hydroxy-chinolon-27-dimethylamino-4-
hydroxy-quinolone-2 silber
grausilver
Gray 2323 N,N-Dime thylamino-
anilin
C N, N-dimethylamino-
aniline
C. l-Methyl-7-dimethyl-
amino-4-hydroxy-chino
lon-2l-methyl-7-dimethyl-
amino-4-hydroxy-quino
lon-2 grau
braunGray
Brown 2424 IlIl 1-Methy1-4-hydroxy-
chinolon-21-methy1-4-hydroxy-
quinolone-2 grau
grünGray
green 2525th IlIl 8-Chlor-4-hydroxy-
chinolon-28-chloro-4-hydroxy
quinolone-2 dunkel
gründark
green 2626th ηη 6-Me thoxy-4-hydroxy-
chinolon-26-methoxy-4-hydroxy
quinolone-2 dunkel
gründark
green 2727 IlIl 1-Methyl -6-dimethyl-
amino-4-hydroxy-chi-
nolon-21-methyl -6-dimethyl-
amino-4-hydroxy-chi-
nolon-2 tannen
grünfir trees
green 2828 ItIt 7-Dimethylamino-4-
hydroxy-chinolon-27-dimethylamino-4-
hydroxy-quinolone-2 grüngraugreen grey 2929 l-Methyl-7-dimethyl-
amino-4-hydroxy-
chinolon-2l-methyl-7-dimethyl-
amino-4-hydroxy
quinolone-2 mattes
graugrünmatt
gray-green 3030th 1-Methy1-4-hydroxy-
chinolon-21-methy1-4-hydroxy-
quinolone-2 grün
graugreen
Gray 3131 8-chlor-4-hydroxy-
chinolon-28-chloro-4-hydroxy
quinolone-2 3232 6-Methy1-4-hydroxy-
chinolon-26-methy1-4-hydroxy-
quinolone-2 3333 6-Methoxy-4-hydroxy-
chinolon-26-methoxy-4-hydroxy
quinolone-2 3434

409885/1 3 Λ 3409885/1 3 Λ 3

Henkel & CIeHenkel & CIe GmbH s«·· na''«""11··11™!» Iy7\l± GmbH s «·· na ''« "" 11 ·· 11 ™! » Iy7 \ l ± KupplerCoupler Farbtonhue Beispiel-
Nr.Example-
No. Entwicklerdeveloper l,6-Dimethyl-4-
hydroxy-chinolon-21,6-dimethyl-4-
hydroxy-quinolone-2 gelb
braunyellow
Brown 3535 N,N-Dimethylamino-
anilinN, N-dimethylamino
aniline 7-Dimethylamino-4-
hydroxy-chinolon-27-dimethylamino-4-
hydroxy-quinolone-2 hell
blondbright
blond 3636 N-Methyl-benz-thia-
zolon-2-hydrazonN-methyl-benz-thia-
zolon-2-hydrazone 1-Methy1-7-dimethy1-1-Methy1-7-dimethy1- blass-pale- 3737 ItIt

1-Methyl-pyridon 2-hydrazon1-methyl-pyridone 2-hydrazone

amino-4-hydroxy-chine- rot lon-2amino-4-hydroxy-quinine red lon-2

1-Methy1-4-hydroxy- rot-1-Methy1-4-hydroxy- red-

chinolon-2 goldquinolone-2 gold

ß-Chlor-^-hydroxy- gelb-ß-chlorine - ^ - hydroxy- yellow-

chinolon-2 organgequinolone-2 organge

7-Dimethylamino- braun-7-dimethylamino brown

4-hydroxy-chinolon-2 grau4-hydroxy-quinolone-2 gray

l-Methyl-7-dimethylamino-4-hydroxychinolon-2 1-methyl-7-dimethylamino-4-hydroxyquinolone-2

l-Methyl-4-hydroxychinolon-2 l-methyl-4-hydroxyquinolone-2

8-Chlor-4-hydroxychinolon-2 8-chloro-4-hydroxyquinolone-2

l-Methyl-6-dimethylamino-4-hydroxychinolon-2 1-methyl-6-dimethylamino-4-hydroxyquinolone-2

rotbraunred-brown

braunviolett brown purple

blaugrau blue-gray

ge Iborange ge Iborange

- 10 -- 10 -

409885/1343409885/1343

Claims (1)

PatentansprücheClaims 1) Haarfärbemittel auf Basis von Oxidationsfarbstoffen, dadurch gekennzeichnet, daß man als Kupplerkomponente 4-Hydroxy-chinolon-2-derivate der allgemeinen Formel1) Hair dyes based on oxidation dyes, characterized in that one is used as the coupler component 4-Hydroxy-quinolone-2-derivatives of the general formula = 0= 0 in der R Wasserstoff oder einen gerad- oder verzweigtkettigen Alkylrest mit 1-4 Kohlenstoffatomen, Rf Wasserstoff, einen gerad- oder verzweigtkettigen Alkylrest mit 1-4 Kohlenstoffatomen, ein Halogenatom, eine Hydroxylgruppe, eine niedere Alkoxygruppe, eine /9-Hydroxy äthylgruppe oder eine Dialkylamlnogruppe mit Alkylresten mit 1-4 Kohlenstoffatomen bedeuten, verwendet.in which R is hydrogen or a straight or branched chain alkyl radical with 1-4 carbon atoms, R f is hydrogen, a straight or branched chain alkyl radical with 1-4 carbon atoms, a halogen atom, a hydroxyl group, a lower alkoxy group, a / 9-hydroxy ethyl group or a dialkylamino group with alkyl radicals having 1-4 carbon atoms is used. 409885/1343409885/1343
DE19732334738 1973-07-09 1973-07-09 Hair-dyestuff for oxidation-dyeing process - contg. 4-hydroxy-quinolone-2-derivs as coupling components Pending DE2334738A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19732334738 DE2334738A1 (en) 1973-07-09 1973-07-09 Hair-dyestuff for oxidation-dyeing process - contg. 4-hydroxy-quinolone-2-derivs as coupling components

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19732334738 DE2334738A1 (en) 1973-07-09 1973-07-09 Hair-dyestuff for oxidation-dyeing process - contg. 4-hydroxy-quinolone-2-derivs as coupling components

Publications (1)

Publication Number Publication Date
DE2334738A1 true DE2334738A1 (en) 1975-01-30

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1981000811A1 (en) * 1979-09-28 1981-04-02 Wella Ag Means and process allowing hair coloration by oxidation
WO2000038633A1 (en) * 1998-12-23 2000-07-06 Henkel Kommanditgesellschaft Auf Aktien Agent for dying keratin fibers
US6566372B1 (en) * 1999-08-27 2003-05-20 Ligand Pharmaceuticals Incorporated Bicyclic androgen and progesterone receptor modulator compounds and methods
FR2841777A1 (en) * 2002-07-05 2004-01-09 Oreal New 2-pyridone hydrazones useful as developers in oxidation dye compositions for dyeing keratinic fibers, especially human hair
FR2841779A1 (en) * 2002-07-05 2004-01-09 Oreal Composition for dyeing keratinic fibers, e.g. human hair, comprises a heteroaromatic hydrazone, an aldehyde precursor and an enzyme capable of generating an aldehyde from the precursor
EP1428510A1 (en) * 2002-12-13 2004-06-16 L'oreal Dyeing composition comprising a tertiary paraphenylenediamine containing a pyrrolidine, and a heterocyclic coupler or a hydroxybenzamide ; method and use
WO2004078153A1 (en) * 2003-03-05 2004-09-16 Wella Aktiengesellschaft Agent and method for dyeing keratin fibres
US7594936B2 (en) 2002-07-05 2009-09-29 L'oreal S.A. Dye composition for keratin fibers containing an aldehyde precursor, enzyme and hydrazone, and method using this composition
US7816372B2 (en) 2003-08-22 2010-10-19 Ligand Pharmaceuticals Incorporated 6-cycloamino-2-quinolinone derivatives as androgen receptor modulator compounds

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1981000811A1 (en) * 1979-09-28 1981-04-02 Wella Ag Means and process allowing hair coloration by oxidation
EP0026474A1 (en) * 1979-09-28 1981-04-08 Wella Aktiengesellschaft Composition and process for oxidative dyeing of hair
WO2000038633A1 (en) * 1998-12-23 2000-07-06 Henkel Kommanditgesellschaft Auf Aktien Agent for dying keratin fibers
US6566372B1 (en) * 1999-08-27 2003-05-20 Ligand Pharmaceuticals Incorporated Bicyclic androgen and progesterone receptor modulator compounds and methods
US7696246B2 (en) 1999-08-27 2010-04-13 Ligand Pharmaceuticals Incorporated Bicyclic androgen and progesterone receptor modulator compounds and methods
EP1415642A1 (en) * 2002-07-05 2004-05-06 L'oreal Composition for dyeing keratinous fibres containing an aldehyde precursor, an enzyme and a hydrazone
FR2841779A1 (en) * 2002-07-05 2004-01-09 Oreal Composition for dyeing keratinic fibers, e.g. human hair, comprises a heteroaromatic hydrazone, an aldehyde precursor and an enzyme capable of generating an aldehyde from the precursor
US7594936B2 (en) 2002-07-05 2009-09-29 L'oreal S.A. Dye composition for keratin fibers containing an aldehyde precursor, enzyme and hydrazone, and method using this composition
FR2841777A1 (en) * 2002-07-05 2004-01-09 Oreal New 2-pyridone hydrazones useful as developers in oxidation dye compositions for dyeing keratinic fibers, especially human hair
EP1428510A1 (en) * 2002-12-13 2004-06-16 L'oreal Dyeing composition comprising a tertiary paraphenylenediamine containing a pyrrolidine, and a heterocyclic coupler or a hydroxybenzamide ; method and use
FR2848434A1 (en) * 2002-12-13 2004-06-18 Oreal TINCTORIAL COMPOSITION COMPRISING CATIONIC TERTIARY PARAPHENYLENEDIAMINE AND HETEROCYCLIC COUPLER, METHODS AND USES
WO2004078153A1 (en) * 2003-03-05 2004-09-16 Wella Aktiengesellschaft Agent and method for dyeing keratin fibres
US7291183B2 (en) 2003-03-05 2007-11-06 Wella Ag Agent and method for dyeing keratin fibers
US7816372B2 (en) 2003-08-22 2010-10-19 Ligand Pharmaceuticals Incorporated 6-cycloamino-2-quinolinone derivatives as androgen receptor modulator compounds

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