DE19543988A1 - Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate - Google Patents
Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-TriaminopyrazolderivateInfo
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- DE19543988A1 DE19543988A1 DE19543988A DE19543988A DE19543988A1 DE 19543988 A1 DE19543988 A1 DE 19543988A1 DE 19543988 A DE19543988 A DE 19543988A DE 19543988 A DE19543988 A DE 19543988A DE 19543988 A1 DE19543988 A1 DE 19543988A1
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- amino
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/32—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using oxidation dyes
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- Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Textile Engineering (AREA)
- Cosmetics (AREA)
Description
Gegenstand der Erfindung sind Mittel zur oxidativen
Färbung von Haaren auf der Basis von 3,4,5-Triamino
pyrazolderivaten als Entwicklersubstanz sowie neue
3,4,5-Triaminopyrazolderivate.
Auf dem Gebiet der Haarfärbung haben Oxidations
farbstoffe eine wesentliche Bedeutung erlangt. Die
Färbung entsteht hierbei durch Reaktion bestimmter
Entwicklersubstanzen mit bestimmten Kupplersubstanzen
in Gegenwart eines geeigneten Oxidationsmittels.
Als Entwicklersubstanzen werden insbesondere 2,5-
Diaminotoluol, 2,5 -Diaminophenylethylalkohol, p-
Aminophenol und 1,4-Diaminobenzol eingesetzt. Von den
vorzugsweise verwendeten Kupplersubstanzen sind
Resorcin, 4-Chlorresorcin, 1-Naphthol, 3-Aminophenol,
5-Amino-2-methylphenol und Derivate des m-Phenylen
diamins zu nennen.
An Oxidationsfarbstoffe, die zur Färbung menschlicher
Haare verwendet werden, sind zahlreiche besondere
Anforderungen gestellt. So müssen sie in toxikolo
gischer und dermatologischer Hinsicht unbedenklich sein
und Färbungen in der gewünschten Intensität ermög
lichen. Ferner wird für die erzielten Haarfärbungen eine
gute Licht-, Dauerwell-, Säure und Reibeechtheit
gefordert. Auf jeden Fall aber müssen solche Haar
färbungen ohne Einwirkung von Licht, Reibung und
chemischen Mitteln über einen Zeitraum von mindestens
4 bis 6 Wochen stabil bleiben. Außerdem ist es er
forderlich, daß durch Kombination geeigneter Ent
wickler- und Kupplerkomponenten eine breite Palette
verschiedener Farbnuancen erzeugt werden kann. Zur
Erzielung natürlicher und besonders modischer Nuancen
im Rotbereich wird vor allem 4-Aminophenol, allein oder
im Gemisch mit anderen Entwicklersubstanzen in Kombina
tion mit geeigneten Kupplungssubstanzen eingesetzt.
Gegen den für den Rotbereich der Farbskala bisher
hauptsächlich eingesetzten Entwickler 4-Aminophenol
wurden in letzter Zeit Bedenken in bezug auf die
physiologische Verträglichkeit erhoben, während die in
neuerer Zeit empfohlenen Entwicklersubstanzen, wie zum
Beispiel Pyrimidinderivate, in färberischer Hinsicht
nicht völlig zufriedenstellen können.
Die in der DE-OS 21 60 317 beschriebenen Pyrazol
derivate, wie zum Beispiel das 3-Amino-1-phenyl-2-
pyrazolon-5, färben Haare nur in sehr geringen, für die
Haarfärbepraxis unbrauchbaren, Farbtiefen an.
Es bestand daher die Aufgabe, ein Oxidationshaarfärbe
mittel auf der Basis einer Entwicklersubstanz/Kuppler
substanz-Kombination zur Verfügung zu stellen, in dem
eine Entwicklersubstanz für den Rotbereich enthalten
ist, welche physiologisch sehr gut verträglich ist und
mit üblichen Kupplersubstanzen das Haar in brillanten
roten Farbtönen mit einer hohen Farbtiefe färbt.
Hierzu wurde nun gefunden, daß durch ein Mittel zur
oxidativen Färbung von Haaren auf der Basis einer
Entwicklersubstanz-Kupplersubstanz-Kombination, welche
als Entwicklersubstanz ein 3,4,5-Triaminopyrazol der
allgemeinen Formel (I),
in der R¹ gleich Wasserstoff, Alkyl mit 1 bis 4 Koh
lenstoffatomen oder Hydroxyalkyl mit 2 bis 4 Kohlen
stoffatomen darstellt und R² Wasserstoff, Alkyl mit 1
bis 4 Kohlenstoffatomen oder Hydroxyalkyl mit 2
bis 4 Kohlenstoffatomen bedeutet, oder dessen phy
siologisch verträgliche, wasserlösliche Salze enthält,
diese Aufgabe in hervorragender Weise gelöst wird.
In dem Haarfärbemittel sollen die Entwicklersubstanzen
der Formel (I), von denen das 1-Methyl-3,4,5-triamino
pyrazol, das 3,5-Diamino-1-methyl-4-methylaminopyrazol
und das 3,5-Diamino-4-(2′-hydroxyethyl) amino-1-methyl
pyrazol bevorzugt ist, in einer Menge von 0,01 bis
3,0 Gewichtsprozent, vorzugsweise in einer Menge von
0,1 bis 2,5 Gewichtsprozent, enthalten sein.
Obwohl die vorteilhaften Eigenschaften der hier
beschriebenen neuen Entwicklersubstanzen es nahelegen,
diese als alleinige Entwicklersubstanz zu verwenden,
ist es selbstverständlich auch möglich, die Ent
wicklersubstanzen der Formel (I) gemeinsam mit be
kannten Entwicklersubstanzen, wie zum Beispiel 1,4-
Diaminobenzol, 2,5-Diaminotoluol oder 2, 5-Diamino
phenylethylalkohol, einzusetzen.
Als Kupplersubstanzen kommen vorzugsweise α-Naphthol,
Resorcin, 4-Chlorresorcin, 2-Methylresorcin, 2-Amino-4-
(2′-hydroxyethyl) amino-anisol, 2,4-Diaminophenyl
alkohol, m-Phenylendiamin, 5-Amino-2-methylphenol, 2,4-
Diaminophenoxyethanol, 4-Amino-2-hydroxyphenoxyethanol,
3-Aminophenol, 3-Amino-2-methylphenol, 4-Hydroxy-1,2-
methylendioxybenzol, 4-Amino-1,2-methylendioxybenzol,
4-(2′-Hydroxyethyl) amino-1-2,-methylendioxybenzol, 2,4-
Diamino-5-fluortoluol, 4-Amino-5-fluor-2-hydroxytoluol,
2,4-Diaminobenzylalkohol, 2,4-Diamino-phenetol, 2,4-
Diamino-5-methylphenetol, 4-Hydroxyindol, 3-Amino-5-
hydroxy-2, 6-dimethoxypyridin und 3,5-Diamino-2,6-
dimethoxypyridin in Betracht.
Die Kuppler- und Entwicklersubstanzen können in dem
Haarfärbemittel jeweils einzeln oder im Gemisch mit
einander enthalten sein.
Die Gesamtmenge der in dem hier beschriebenen Haar
färbemittel enthaltenen Entwicklersubstanz-Kuppler
substanz-Kombination beträgt 0,1 bis 5,0 Gewichts
prozent, wobei eine Menge von 0,5 bis 4,0 Gewichts
prozent bevorzugt ist. Die Entwicklerkomponenten werden
im allgemeinen in etwa äquimolaren Mengen, bezogen auf
die Kupplerkomponenten, eingesetzt. Es ist jedoch nicht
nachteilig, wenn die Entwicklerkomponenten diesbezüg
lich in einem gewissen Überschuß oder Unterschuß
vorhanden sind.
Weiterhin kann das erfindungsgemäße Haarfärbemittel
zusätzlich andere Farbkomponenten, beispielsweise 6-
Amino-2-methylphenol und 2-Amino-5-methylphenol, sowie
ferner übliche direktziehende Farbstoffe, zum Beispiel
Triphenylmethanfarbstoffe wie 4-[(4′aminophenyl)-(4′-
imino-2′′,5′′-cyclohexadien-1′′-yliden)-methyl]-2-methyl
aminobenzol-monohydrochlorid (C.I. 42 510) und 4-
[(4′amino-3′-methyl-phenyl)-(4′′-imino-3′′-methyl-2′′,5′′-
cyclohexadien-1′′-yliden)-methyl]-2-methyl-aminobenzol
mohohydrochlorid (C.I. 42 520), aromatische Nitrofarb
stoffe wie 2-Nitro-1,4-diaminobenzol, 2-Amino-4-nitro
phenol, 2-Amino-5-nitrophenol, 2-Amino-4-6-dinitro
phenol, 2-Amino-5-(2′-hydroxyethyl) amino-nitrobenzol
und 2-Methylamino-5-bis-(2′-hydroxyethyl) amino-nitro
benzol, Azofarbstoffe wie 6-[(4′-Aminophenyl) azo]-5-
hydroxy-naphthalin-1-sulfonsäure-Natriumsalz (C.I.
14 805) und Dispersionsfarbstoffe wie beispielsweise
1,4-Diaminoanthrachinon und 1,4,5,8-Tetraamino
anthrachinon enthalten. Die Haarfärbemittel können
diese Farbkomponenten in einer Menge von etwa 0,1 bis
4,0 Gewichtsprozent enthalten.
Selbstverständlich können die Kuppler- und Entwickler
substanzen sowie die anderen Farbkomponenten, sofern es
Basen sind, auch in Form der physiologisch verträg
lichen Salze mit organischen oder anorganischen Säuren,
wie beispielsweise Salzsäure oder Schwefelsäure,
beziehungsweise - sofern sie aromatische OH-Gruppen
besitzen - in Form der Salze mit Basen, zum Beispiel
als Alkaliphenolate, eingesetzt werden.
Darüber hinaus können in dem Haarfärbemittel noch
weitere übliche kosmetische Zusätze, beispielsweise
Antioxidantien wie Ascorbinsäure, Thioglykolsäure oder
Natriumsulfit, sowie Parfümöle, Komplexbildner, Netz
mittel, Emulgatoren, Verdicker und Pflegestoffe ent
halten sein.
Die Zubereitungsform des neuen Haarfärbemittels kann
beispielsweise eine Lösung, insbesondere eine wäßrige
oder wäßrig-alkoholische Lösung sein. Die besonders
bevorzugten Zubereitungsformen sind jedoch eine Creme,
ein Gel oder eine Emulsion. Ihre Zusammensetzung stellt
eine Mischung der Farbstoffkomponenten mit den für
solche Zubereitungen üblichen Zusätzen dar.
Übliche Zusätze in Lösungen, Cremes, Emulsionen oder
Gelen sind zum Beispiel Lösungsmittel wie Wasser,
niedere aliphatische Alkohole, beispielsweise Ethanol,
Propanol oder Isopropanol, Glycerin oder Glykole wie
1,2-Propylenglykol, weiterhin Netzmittel oder Emulga
toren aus den Klassen der anionischen, kationischen,
amphoteren oder nichtionogenen oberflächenaktiven Sub
stanzen wie Fettalkoholsulfate, oxethylierte Fettal
kohlsulfate, Alkylsulfonate, Alkylbenzolsulfonate,
Alkyltrimethylammoniumsalze, Alkylbetaine, oxethylierte
Fettalkohole, oxethylierte Nonylphenole, Fettsäure
alkanolamide, oxethylierte Fettsäureester, ferner
Verdicker wie höhere Fettalkohole, Stärke, Cellulose
derivate, Petrolatum, Paraffinöl und Fettsäuren sowie
außerdem Pflegestoffe wie kationische Harze, Lanolin
derivate, Cholesterin, Pantothensäure und Betain. Die
erwähnten Bestandteile werden in den für solche Zwecke
üblichen Mengen verwendet, zum Beispiel die Netzmittel
und Emulgatoren in Konzentrationen von etwa 0,5 bis
30 Gewichtsprozent, die Verdicker in einer Menge von
etwa 0,1 bis 25 Gewichtsprozent und die Pflegestoffe in
einer Konzentration von etwa 0,1 bis 5,0 Gewichts
prozent.
Je nach Zusammensetzung kann das erfindungsgemäße
Haarfärbemittel schwach sauer, neutral oder alkalisch
reagieren. Insbesondere weist es einen pH-Wert von 6,0
bis 11,5 auf, wobei die basische Einstellung mit
Ammoniak erfolgt. Es können aber auch organische Amine,
zum Beispiel Monoethanolamin und Triethanolamin, oder
auch anorganische Basen wie Natriumhydroxid und Kalium
hydroxid Verwendung finden. Für eine pH-Einstellung im
sauren Bereich kommen zum Beispiel Phosphorsäure sowie
Essigsäure oder andere organische Säuren, wie zum
Beispiel Zitronensäure oder Weinsäure, in Betracht.
Für die Anwendung zur oxidativen Färbung von Haaren
vermischt man das vorstehend beschriebene Haarfärbe
mittel unmittelbar vor dem Gebrauch mit einem Oxida
tionsmittel und trägt eine für die Haarfärbebehandlung
ausreichende Menge, je nach Haarfülle, im allgemeinen
etwa 60 bis 200 g, dieses Gemisches auf das Haar auf.
Als Oxidationsmittel zur Entwicklung der Haarfärbung
kommen hauptsächlich Wasserstoffperoxid oder dessen
Additionsverbindungen an Harnstoff, Melamin oder
Natriumborat in Form einer 3- bis 12-prozentigen,
vorzugsweise 6-prozentigen, wäßrigen Lösung, aber auch
Luftsauerstoff in Betracht. Wird eine 6-prozentige
Wasserstoffperoxid- Lösung als Oxidationsmittel ver
wendet, so beträgt das Gewichtsverhältnis zwischen
Haarfärbemittel und Oxidationsmitte 5 : 1 bis 1 : 2, vor
zugsweise jedoch 1 : 1. Größere Mengen an Oxidations
mittel werden vor allem bei höheren Farbstoffkonzen
trationen im Haarfärbemittel oder wenn gleichzeitig
eine stärkere Bleichung des Haares beabsichtigt ist
verwendet. Man läßt das Gemisch bei 15 bis 50 Grad
Celsius etwa 10 bis 45 Minuten lang, vorzugsweise
30 Minuten lang, auf das Haar einwirken, spült sodann
das Haar mit Wasser aus und trocknet es. Gegebenenfalls
wird im Anschluß an diese Spülung mit einem Shampoo
gewaschen und eventuell mit einer schwachen organischen
Säure, wie zum Beispiel Zitronensäure oder Weinsäure,
nachgespült. Anschließend wird das Haar getrocknet.
Die in dem erfindungsgemäßen Haarfärbemitteln
enthaltenen 3,4,5-Triamino-pyrazole der allgemeinen
Formel (I) lassen sich gut nach folgendem Schema
herstellen:
Die Salze der Verbindungen der Formel (I) sollen in dem
Haarfärbemittel entweder als freie Basen oder in Form
ihrer physiologisch verträglichen Salze mit anorga
nischen oder organischen Säuren, wie zum Beispiel
Salzsäure, Milchsäure oder Zitronensäure, eingesetzt
werden. Die Verbindungen der Formen (I) sind gut in
Wasser löslich und sie weisen zusätzlich eine ausge
zeichnete Lagerstabilität, insbesondere als Bestandteil
der hier beschriebenen Haarfärbemittel, auf.
Das erfindungsgemäße Haarfärbemittel mit einem Gehalt
an 3,4,5-Triaminopyrazolderivaten als Entwicklersub
stanzen ermöglicht Haarfärbungen mit ausgezeichneter
Farbechtheit, insbesondere was die Licht-, Wasch- und
Reibeechtheit anbetrifft.
Hinsichtlich der färberischen Eigenschaften bieten die
erfindungsgemäßen Haarfärbemittel Möglichkeiten, die
weit über einen Ersatz der üblicherweise verwendeten 4-
Aminophenole hinausgehen. So lassen sich brillante Rot
töne mit außerordentlicher Farbtiefe erzeugen, wie sie
mit den gängigen Farbkomponenten nicht zu erzielen
sind. Neben dieser Anwendung im hochmodischen Bereich
können aber auch durch die Verwendung in Kombination
mit geeigneten Kupplungskomponenten natürliche Farbtöne
erzeugt werden, ohne daß eine weitere Entwicklungskom
ponente vom Typ der p-Phenylendiamine erforderlich
wäre.
Die sehr guten färberischen Eigenschaften der Haar
färbemittel gemäß der vorliegenden Anmeldung zeigen
sich weiterhin darin, daß diese Mittel eine Anfärbung
von ergrauten, chemisch nicht vorgeschädigten Haaren
problemlos und mit guter Deckkraft ermöglichen.
Gegenstand der vorliegenden Patentanmeldung sind ferner
die neuen 3,4,5-Triaminpyrazolderivate der allgemeinen
Formel (I), wobei insbesondere 1-Methyl-3,4-5-triamino
pyrazol, 3,5-Diamino-1-methyl-4-methylamino-pyrazol und
3,5-Diamono-4-(2′-hydroxyethyl) amino-1-methylpyrazol zu
nennen sind.
Die nachfolgenden Beispiele sollen den Gegenstand der
Erfindung näher erläutern, ohne ihn darauf zu be
schränken.
5 g (20 mmol) 4-Brom-3,5-dinitro-1-methylpyrazol werden
in 20 ml Dimethylsulfoxid (DMSO) mit dem dreifachen
molaren Überschuß an Alkylamin versetzt und 2 Stunden
auf dem Wasserbad erwärmt. Anschließend wird das
Reaktionsprodukt auf Eis gegossen und der Niederschlag
abfiltriert und aus Ethanol umkristallisiert.
Verwendetes Amin: Benzylamin
Es werden 3,46 g (= 63 Prozent der Theorie) 4- Benzylamino-3,5-dinitro-1-methylpyrazol in Form gelber Kristalle erhalten.
Schmelzpunkt: 92°C
Es werden 3,46 g (= 63 Prozent der Theorie) 4- Benzylamino-3,5-dinitro-1-methylpyrazol in Form gelber Kristalle erhalten.
Schmelzpunkt: 92°C
Verwendetes Amin: Methylamin
Es werden 2,71 g(= 67 Prozent der Theorie) 4- Methylamino-3,5-dinitro-1-methylpyrazol in Form gelber Kristalle erhalten.
Schmelzpunkt: 128°C.
Es werden 2,71 g(= 67 Prozent der Theorie) 4- Methylamino-3,5-dinitro-1-methylpyrazol in Form gelber Kristalle erhalten.
Schmelzpunkt: 128°C.
Verwendetes Amin: Ethanolamin
Es werden 2,22 g (= 50 Prozent der Theorie) 4- (2′-Hydroxyethyl) amino-3,5-dinitro-1- methylpyrazol in Form gelber Kristalle erhalten.
Schmelzpunkt: 101 bis 103°C
Es werden 2,22 g (= 50 Prozent der Theorie) 4- (2′-Hydroxyethyl) amino-3,5-dinitro-1- methylpyrazol in Form gelber Kristalle erhalten.
Schmelzpunkt: 101 bis 103°C
10 mmol der entsprechenden Nitroverbindung 1a., 1b.
oder 1c. werden in Methanol unter Verwendung eines
Palladium-Aktivkohle-Katalysators (10%) bei Raumtem
peratur (20 bis 30°C) hydriert. Nach Beendigung der
Reaktion wird vom Katalysator in ein Gemisch aus
Schwefelsäure und Wasser abfiltriert. Nach Zugabe von
Methanol kristallisieren die entsprechenden Sulfate
aus.
Verwendete Nitroverbindung: 1a)
Man erhält 2 g (= 89 Prozent der Theorie) 1- Methyl-3,4,5-Triaminopyrazol-sulfat in Form farbloser Kristalle, welche bei 205°C unter Zersetzung schmelzen.
Man erhält 2 g (= 89 Prozent der Theorie) 1- Methyl-3,4,5-Triaminopyrazol-sulfat in Form farbloser Kristalle, welche bei 205°C unter Zersetzung schmelzen.
Verwendete Nitroverbindung: 1b)
Man erhält 2 g (= 84 Prozent der Theorie) 3,5- Diamino-1-methyl-4-methylaminopyrazol-sulfat in Form farbloser Kristalle, welche bei 214°C unter Zersetzung schmelzen.
Man erhält 2 g (= 84 Prozent der Theorie) 3,5- Diamino-1-methyl-4-methylaminopyrazol-sulfat in Form farbloser Kristalle, welche bei 214°C unter Zersetzung schmelzen.
Verwendete Nitroverbindung: 1c.)
Man erhält 1,6 g (= 59 Prozent der Theorie) 3,5- Diamino-4-(2′-hydroxyethyl) amino-1-methylpyrazol sulfat in Form farbloser Kristalle, welche bei 198°C unter Zersetzung schmelzen.
Man erhält 1,6 g (= 59 Prozent der Theorie) 3,5- Diamino-4-(2′-hydroxyethyl) amino-1-methylpyrazol sulfat in Form farbloser Kristalle, welche bei 198°C unter Zersetzung schmelzen.
1,40 g 1-Methyl-3,4,5-triaminopyrazol-sulfat
0,67 g α-Naphthol
0,28 g 2-Amino-4-(2′-hydroxyethyl)amino-anisolsulfat
15,00 g Cetylalkohol
3,50 g Natrium-laurylalkohol-diglycolethersulfat (28prozentige wäßrige Lösung)
0,30 g Natriumsulfit, wasserfrei
0,19 g NaOH (10prozentige wäßrige Lösung)
1,77 g Ammoniak (25prozentige wäßrige Lösung)
76,89 g
0,67 g α-Naphthol
0,28 g 2-Amino-4-(2′-hydroxyethyl)amino-anisolsulfat
15,00 g Cetylalkohol
3,50 g Natrium-laurylalkohol-diglycolethersulfat (28prozentige wäßrige Lösung)
0,30 g Natriumsulfit, wasserfrei
0,19 g NaOH (10prozentige wäßrige Lösung)
1,77 g Ammoniak (25prozentige wäßrige Lösung)
76,89 g
Wasser
100,00 g
100,00 g
50 g des vorstehenden Haarfärbemittels werden kurz vor
dem Gebrauch mit 50 g Wasserstoffperoxidlösung (6-
prozentig) vermischt und das Gemisch wird anschließend
auf blonde Naturhaare aufgetragen. Nach einer Einwirk
zeit von 30 Minuten bei 40 Grad Celsius wird das Haar
mit Wasser gespült und getrocknet. Das Haar hat eine
intensive auberginefarbene Färbung erhalten.
1,44 g 3,5-Diamino-1-methyl-4-methylaminopyrazolsulfat
0,31 g 5-Amino-2-methyl-phenol
0,36 g α-Naphthol
15,00 g Cetylalkohol
3,50 g Natrium-laurylalkohol-diglycolethersulfat (28prozentige Lösung)
0,30 g Natriumsulfit, wasserfrei
0,19 g NaOH (10prozentige wäßrige Lösung)
1,00 g Ammoniak (25prozentige wäßrige Lösung)
77,90 g
0,31 g 5-Amino-2-methyl-phenol
0,36 g α-Naphthol
15,00 g Cetylalkohol
3,50 g Natrium-laurylalkohol-diglycolethersulfat (28prozentige Lösung)
0,30 g Natriumsulfit, wasserfrei
0,19 g NaOH (10prozentige wäßrige Lösung)
1,00 g Ammoniak (25prozentige wäßrige Lösung)
77,90 g
Wasser
100,00 g
100,00 g
Man vermischt kurz vor dem Gebrauch 50 g des vorstehend
beschriebenen Haarfärbemittels mit 50 g Wasserstoffper
oxidlösung (6-prozentig) und läßt die Mischung
30 Minuten bei 40 Grad Celsius auf blonde Naturhaare
einwirken. Das Haar wird mit Wasser gespült und ge
trocknet. Das Haar wird intensiv purpurrot gefärbt.
Es werden Haarfärbelösungen folgender Zusammensetzung
hergestellt:
Die Haarfärbelösungen werden gemäß Beispiel 3
zubereitet und auf zu 90 Prozent ergraute, menschliche
Haare aufgetragen. Die resultierenden Färbungen sind in
Tabelle 1 zusammengefaßt.
Alle Prozentangaben stellen, soweit nicht anders
angegeben, Gewichtsprozente dar.
Claims (10)
1. Mittel zur oxidativen Färbung von Haaren auf der
Basis einer Entwicklersubstanz-Kupplersubstanz-
Kombination, dadurch gekennzeichnet, daß es als
Entwicklersubstanz ein 3,4,5-Triaminopyrazol der
allgemeinen Formel (I)
in der R¹ Wasserstoff, Alkyl mit 1 bis 4 Kohlen
stoffatomen oder Hydroxyalkyl mit 2 bis 4 Kohlen
stoffatomen darstellt und R² Wasserstoff, Alkyl mit
1 bis 4 Kohlenstoffatomen oder Hydroxyalkyl mit
2 bis 4 Kohlenstoffatomen bedeutet, oder dessen
physiologisch verträgliche, wasserlösliche Salze
enthält.
2. Mittel nach Anspruch 1, dadurch gekennzeichnet, daß
die Entwicklersubstanz der allgemeinen Formel (I)
ausgewählt ist aus 1-Methyl-3,4,5-triaminopyrazol,
3,5-Diamino-1-methyl-4-methylamino-pyrazol und 3,5-
Diamino-4-(2′-Hydroxyethyl) amino-1-methyl-pyrazol.
3. Mittel nach Anspruch 1 oder 2, dadurch gekenn
zeichnet, daß die Entwicklersubstanz der Formel (I)
in einer Menge von 0,01 bis 3,0 Gewichtsprozent
enthalten ist.
4. Mittel nach einem der Ansprüche 1 bis 3, dadurch
gekennzeichnet, daß die Kupplersubstanz ausgewählt
ist, aus α-Naphthol, Resorcin, 4-Chlorresorcin, 2-
Methylresorcin, 2-Amino-4-(2′-hydroxyethyl) amino
anisol, 5-Amino-2-methylphenol, 3-Amino-2-methyl
phenol, 4-Hydroxy-1,2-methylendioxybenzol, 4-Amino-
1,2-methylendioxybenzol, 4-(2′-Hydroxyethyl) amino-
1,2-methylendioxybenzol, 2,4-Diamino-phenetol, 2,4-
Diamino-5-methylphenetol, 2,4-Diamino-5-fluor
toluol, 4-Amino-5-fluor-2-hydroxytoluol, 2,4-
Diaminobenzylalkohol, m-Phenylendiamin, 2,4-
Diaminophenoxyethanol, 4 -Hydroxyindol, 3 -Amino-5-
hydroxy-2,6-dimethoxypyridin und 3,5-Diamino-2,6-
dimethoxy-pyridin.
5. Mittel nach einem der Ansprüche 1 bis 4, dadurch
gekennzeichnet, daß die Gesamtmenge der Ent
wicklersubstanz-Kupplersubstanz-Kombination 0,1 bis
5,0 Gewichtsprozent beträgt.
6. Mittel nach einem der Ansprüche 1 bis 5, dadurch
gekennzeichnet, daß es eine zusätzliche Farb
komponente enthält, die ausgewählt ist aus 6-Amino-
2-methylphenol, 2-Amino-5-methylphenol, 4-[(4′-
aminophenyl)-(4′-imino-2′′, 5′′-cyclohexadien-1′′-
yliden)-methyl]-2-methyl-aminobenzol-monohydro
chlorid (C.I. 42 510), 4-[(4′-amino-3′-methyl
phenyl)-(4′′-imino-3′′-methyl-2′′,5′′-cyclohexachen-1′′-
yliden)-methyl]-2-methyl-aminobenzol-monohydro
chlorid (C.I. 42 520), 2-Nitro-1,4-diaminobenzol,
2-Amino-4-nitro-phenol, 2-Amino-5-nitrophenol, 2-
Amino-4,6-dinitrophenol, 2-Amino-5-(2′-hydroxy
ethyl) amino-nitrobenzol, 2-Methylamino-5-bis- (2′-
hydroxyethyl) amino-nitrobenzol, 6-[(4′-Amino
phenyl)azo]-5-hydroxy-naphthalin-1-sulfonsäure-
Natriumsalz (C.I. 14 805), 1,4-Diamino-anthrachinon
und 1,4,5,8-Tetraaminoanthrachinon.
7. 3,4,5-Triamino-pyrazol der allgemeinen Formel (I)
in der R¹ Wasserstoff, Alkyl mit 1 bis 4 Kohlen
stoffatomen oder Hydroxyalkyl mit 2 bis 4 Kohlen
stoffatomen darstellt und R² Wasserstoff, Alkyl mit
1 bis 4 Kohlenstoffatomen oder Hydroxyalkyl mit 2
bis 4 Kohlenstoffatomen bedeutet.
8. 1-Methyl-3,4,5-triaminopyrazol.
9. 3,5-Diamino-1-methyl-4-methylaminopyrazol.
10. 3,5-Diamino-4-(2′-hydroxyethyl)amino-1-
methylpyrazol.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19543988A DE19543988A1 (de) | 1995-11-25 | 1995-11-25 | Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
JP24721696A JP3657707B2 (ja) | 1995-11-25 | 1996-08-28 | 3、4、5−トリアミノピラゾール誘導体を含有する酸化染毛剤並びに新規3、4、5−トリアミノピラゾール誘導体 |
US08/711,229 US5766576A (en) | 1995-11-25 | 1996-09-09 | Oxidation hair dye compositions containing 3,4,5-triaminopyrazole derivatives and 3,4,5-triaminopyrazole derivatives |
EP96116146A EP0786244B1 (de) | 1995-11-25 | 1996-10-09 | Oxidationshaarfärbemittel mit einem Gehalt an 3, 4, 5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
DE59607717T DE59607717D1 (de) | 1995-11-25 | 1996-10-09 | Oxidationshaarfärbemittel mit einem Gehalt an 3, 4, 5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
ES96116146T ES2105997T3 (es) | 1995-11-25 | 1996-10-09 | Productos para el teñido oxidativo del cabello. |
BR9605695A BR9605695A (pt) | 1995-11-25 | 1996-11-25 | Agente de tingimento de cabelos por oxidaçao com um teor de derivados de 3,4,5-triaminopirazol bem como derivados de 3,4,5-triaminopirazol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19543988A DE19543988A1 (de) | 1995-11-25 | 1995-11-25 | Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
Publications (1)
Publication Number | Publication Date |
---|---|
DE19543988A1 true DE19543988A1 (de) | 1997-05-28 |
Family
ID=7778418
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19543988A Withdrawn DE19543988A1 (de) | 1995-11-25 | 1995-11-25 | Oxidationshaarfärbemittel mit einem Gehalt an 3,4,5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
DE59607717T Expired - Fee Related DE59607717D1 (de) | 1995-11-25 | 1996-10-09 | Oxidationshaarfärbemittel mit einem Gehalt an 3, 4, 5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE59607717T Expired - Fee Related DE59607717D1 (de) | 1995-11-25 | 1996-10-09 | Oxidationshaarfärbemittel mit einem Gehalt an 3, 4, 5-Triaminopyrazolderivaten sowie neue 3,4,5-Triaminopyrazolderivate |
Country Status (6)
Country | Link |
---|---|
US (1) | US5766576A (de) |
EP (1) | EP0786244B1 (de) |
JP (1) | JP3657707B2 (de) |
BR (1) | BR9605695A (de) |
DE (2) | DE19543988A1 (de) |
ES (1) | ES2105997T3 (de) |
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- 1996-09-09 US US08/711,229 patent/US5766576A/en not_active Expired - Lifetime
- 1996-10-09 DE DE59607717T patent/DE59607717D1/de not_active Expired - Fee Related
- 1996-10-09 EP EP96116146A patent/EP0786244B1/de not_active Expired - Lifetime
- 1996-10-09 ES ES96116146T patent/ES2105997T3/es not_active Expired - Lifetime
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WO2022129369A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising two particular oxidation dye precursors, an oxyethylenated fatty acid ester of sorbitan and a fatty acid |
WO2022129373A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors and a particular oxyethylenated fatty acid ester of sorbitan |
WO2022129384A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of at least one fatty substance, a particular carboxylic acid and an oxidation dye and/or an alkaline agent |
WO2022129388A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors and an alkyl(poly)glycoside |
WO2022129352A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Cosmetic composition comprising a combination of two particular couplers and n,n-dicarboxymethylglutamic acid and/or its salts |
WO2022129372A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors and an alkyl(poly)glycoside |
WO2022129357A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Cosmetic composition comprising a combination of two particular couplers and at least one oxidation base |
FR3117828A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de trois précurseurs de coloration d’oxydation particuliers. |
WO2022129394A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising a particular oxidation dyeing base and at least two particular couplers |
FR3117826A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un alkyl(poly)glycoside. |
FR3117812A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition cosmétique comprenant une association de deux coupleurs particuliers et de l’acide N,N-dicarboxyméthyl glutamique et/ou ses sels |
FR3117835A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un alkyl(poly)glycoside. |
FR3117814A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant une base de coloration d’oxydation particuliere, au moins une gomme de guar et au moins un corps gras. |
FR3117866A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant une base de coloration d’oxydation particuliere, au moins un polymère associatif et au moins un corps gras. |
FR3117837A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier et un acide carboxylique particulier |
FR3117841A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant deux précurseurs de coloration d’oxydation particuliers, et un acide carboxylique particulier |
WO2022129393A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising a particular oxidation dyeing base, at least one associative polymer and at least one fatty substance |
FR3117817A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition cosmétique comprenant une association de deux coupleurs particuliers et au moins une base d’oxydation |
FR3117839A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et d’un acide carboxylique particulier |
FR3117816A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant une base de coloration d’oxydation particuliere et au moins deux coupleurs particuliers. |
FR3117819A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | COMPOSITION COLORANTE A BASE DE 2-γ-HYDROXYPROPYL-PARA-PHENYLENEDIAMINE ET D’UN TENSIOACTIF PHOSPHORIQUE |
FR3117829A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un alkyl(poly)glycoside. |
FR3117838A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un ester d’acide gras et de sorbitane oxyéthyléné particulier. |
WO2022129350A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Cosmetic composition comprising a combination of two particular couplers and an oxyethylenated fatty acid ester of sorbitan |
FR3117836A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un alkyl(poly)glycoside. |
WO2022129386A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising a particular oxidation dyeing base, at least one guar gum and at least one fatty substance |
FR3117827A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier et un acide carboxylique particulier |
FR3117830A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant une base de coloration d’oxydation particuliere, au moins un coupleur particulier et au moins un corps gras. |
FR3117815A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition cosmétique comprenant une association de deux coupleurs particuliers et un tensioactif non ionique de type alkylpolyglycoside |
WO2022129377A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors and a particular carboxylic acid |
FR3117840A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition comprenant deux précurseurs de coloration d’oxydation particuliers, un ester d’acide gras et de sorbitane oxyéthyléné et un acide gras |
WO2022129380A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising a particular oxidation dye precursor and a particular carboxylic acid |
FR3117811A1 (fr) | 2020-12-17 | 2022-06-24 | L'oreal | Composition cosmétique comprenant une association de deux coupleurs particuliers et un ester oxyéthyléné d'acide gras et de sorbitane |
WO2022129383A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Process for dyeing keratin fibres with a composition comprising a particular oxidation dye precursor, a particular carboxylic acid and a chemical oxidizing agent |
WO2022129391A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors and an alkyl(poly)glycoside |
WO2022129364A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of three particular oxidation dye precursors |
WO2022129349A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Dyeing composition based on 2-gamma-hydroxypropyl-para-phenylenediamine and a phosphoric surfactant |
WO2022129385A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors, an alkyl(poly)glycoside and a sulfated anionic surfactant |
WO2022129379A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Composition comprising two particular oxidation dye precursors, and a particular carboxylic acid |
WO2022129355A1 (en) | 2020-12-17 | 2022-06-23 | L'oreal | Cosmetic composition comprising a combination of two particular couplers and a nonionic surfactant of alkylpolyglycoside type |
FR3117806A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Composition pour la décoloration et la coloration simultanées des fibres kératiniques et procédé mettant en œuvre cette composition |
WO2022129344A1 (en) | 2020-12-18 | 2022-06-23 | L'oreal | Composition for lightening keratin fibres and process for lightening keratin fibres using this composition |
WO2022129345A1 (en) | 2020-12-18 | 2022-06-23 | L'oreal | Process for lightening keratin fibres |
WO2022129347A1 (en) | 2020-12-18 | 2022-06-23 | L'oreal | Composition for the simultaneous bleaching and dyeing of keratin fibres and process using this composition |
FR3117809A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3117823A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Procédé de coloration capillaire mettant en oeuvre des dérivés particuliers de résorcinol, compositions associées et nouveaux composés |
FR3117808A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Composition pour la décoloration et la coloration simultanées des fibres kératiniques et procédé mettant en œuvre cette composition |
WO2022129346A1 (en) | 2020-12-18 | 2022-06-23 | L'oreal | Composition for the simultaneous bleaching and dyeing of keratin fibres and process employing this composition |
FR3117807A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
WO2022129343A1 (en) | 2020-12-18 | 2022-06-23 | L'oreal | Process for lightening keratin fibres |
FR3117805A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
FR3118707A1 (fr) | 2021-01-08 | 2022-07-15 | L'oreal | Composition solide pour la teinture et/ou l’éclaircissement des fibres kératineuses |
FR3122814A1 (fr) | 2021-05-12 | 2022-11-18 | L'oreal | Dispositif pour la coloration d’oxydation des fibres kératiniques |
WO2022238545A1 (en) | 2021-05-12 | 2022-11-17 | L'oreal | Device for the oxidation dyeing of keratin fibres |
WO2023275206A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising n,n-dicarboxymethylglutamic acid, at least one fatty alcohol, at least one fatty acid, at least one polyol, at least one alkaline agent and optionally at least one dye |
FR3124719A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins un coupleur particulier, au moins une base d’oxydation particulière, au moins un corps gras et au moins un polysaccharide anionique. |
FR3124721A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Un kit de teinture |
FR3124713A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant de l’acide N,N-dicarboxyméthyl glutamique, du propane-1,3-diol, au moins un tensioactif non ionique, au moins un agent alcalin et/ou au moins un colorant |
FR3124716A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins une alcanolamine, un (méta)silicate, la glycine et l’acide N,N-dicarboxyméthyl glutamique. |
FR3124724A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins un alkyl(poly)glycoside, au moins un alcool gras, au moins un acide gras, et au moins un agent alcalin |
FR3124733A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins une base d’oxydation, au moins agent alcalin, et un corps gras issu du karité |
FR3124706A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins une alcanolamine, un (méta)silicate, la glycine et un acide gras. |
FR3124709A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins une alcanolamine, un (méta)silicate, la glycine et le propane-1,3-diol. |
FR3124702A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant du propane-1,3-diol et au moins un corps gras et un ou plusieurs agents alcalins et/ou un ou plusieurs colorants. |
FR3124720A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins un coupleur particulier, au moins un agent alcalin et au moins un alcool gras liquide et au moins un alcool gras solide. |
FR3124727A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant une alcanolamine, un (méta)silicate, la glycine, un colorant et un polysaccharide. |
FR3124705A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant du propan-1,3-diol, au moins une alcanolamine, au moins un corps gras et éventuellement au moins un polyol |
FR3124732A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant du karité, un alkyl(poly)glycoside, un polysaccharide et un agent alcalin et/ou un colorant |
FR3124707A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins une base particulière, le propane-1,3-diol, au moins un agent alcalin et au moins un corps gras. |
FR3124712A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition cosmétique comprenant de l’acide N,N-dicarboxyméthyl glutamique, au moins un ester oxyéthyléné d'acide gras en C8-C30 et de sorbitane, au moins un corps gras, au moins un agent alcalin et/ou un agent colorant |
FR3124714A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition cosmétique comprenant au moins un alkyl(poly)glycoside, de l’acide N,N-dicarboxyméthyl glutamique, du propane-1,3-diol, au moins un corps gras différent des acides gras, au moins un agent alcalin et/ou un agent colorant |
FR3124715A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant de l’acide N,N-dicarboxyméthyl glutamique, au moins un alcool gras, au moins un acide gras, au moins un polyol, au moins un agent alcalin et éventuellement au moins un colorant |
FR3124725A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins un tensioactif non ionique, du propane-1,3-diol, au moins un corps gras, au moins un agent alcalin et/ou au moins un agent colorant |
FR3124731A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins un coupleur d’oxydation particulier, au moins un corps gras issu du karité et au moins un agent alcalin |
FR3124722A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition retardatrice d’oxydation |
FR3124708A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins une base particulière, au moins un agent alcalin et au moins un alcool gras liquide et au moins un alcool gras solide. |
FR3124710A1 (fr) | 2021-06-30 | 2023-01-06 | L'oreal | Composition comprenant au moins un coupleur particulier, le propane-1,3-diol, au moins un agent alcalin et au moins un corps gras. |
WO2023275193A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one oxidation dye, 1,3-propanediol, at least one alkaline agent and at least one fatty substance |
WO2023275168A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one particular coupler, at least one particular oxidation base, at least one fatty substance and at least one anionic polysaccharide |
WO2023275198A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising an alkanolamine, a (meta)silicate, glycine, a dye and a polysaccharide |
WO2023275210A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising 1,3-propanediol and at least one fatty substance, one or more oxidation dyes |
WO2023275204A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one alkyl (poly)glycoside, at least one fatty alcohol, at least one fatty acid, and at least one alkaline agent |
WO2023278726A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Compositions containing direct dyes for imparting color and tone to the hair |
WO2023275207A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising propane-1,3-diol, at least one alkanolamine, at least one fatty substance and optionally at least one polyol |
WO2023275208A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least nonionic surfactant, 1,3-propanediol, at least one fatty substance, at least one colouring agent |
WO2023275187A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising shea, an alkyl(poly)glycoside, a polysaccharide and a dye |
WO2023275197A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one oxidation dye, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol |
WO2023275205A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Cosmetic composition comprising at least one alkyl (poly)glycoside, n,n-dicarboxymethylglutamic acid, propane-1,3-diol, at least one fatty substance other than fatty acids, at least one dye |
US12109289B2 (en) | 2021-06-30 | 2024-10-08 | L'oreal | Compositions for imparting color and tone to the hair |
WO2023275170A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one alkanolamine, a (meta)silicate, glycine and 1,3-propanediol |
WO2023275209A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising n,n-dicarboxymethylglutamic acid, 1,3-propanediol, at least one nonionic surfactant, at least one alkaline agent and/or at least one dye |
US12036299B2 (en) | 2021-06-30 | 2024-07-16 | L'oreal | Compositions containing direct dyes for imparting color and tone to the hair |
WO2023275211A1 (en) | 2021-06-30 | 2023-01-05 | L'oreal | Composition comprising at least one particular oxidation dye, at least one shea-derived fatty substance and at least one alkaline agent |
WO2023034391A1 (en) | 2021-08-31 | 2023-03-09 | L'oreal | Compositions, kits, and methods for altering the color of hair |
US11707420B2 (en) | 2021-08-31 | 2023-07-25 | L'oreal | Compositions, kits, and methods for altering the color of hair |
FR3127130A1 (fr) | 2021-09-17 | 2023-03-24 | L'oreal | Compositions pour CONFÉRER UNE couleur et UN TON aux cheveux |
FR3127131A1 (fr) | 2021-09-17 | 2023-03-24 | L'oreal | Compositions pour CONFÉRER UNE couleur et UN TON aux cheveux |
FR3127400A1 (fr) | 2021-09-30 | 2023-03-31 | L'oreal | Procédé de coloration et/ou d’éclaircissement des fibres kératiniques comprenant une étape de coloration et/ou d’éclaircissement des fibres kératiniques et une étape de traitement des fibres kératiniques par une composition comprenant au moins une huile végétale. |
FR3127694A1 (fr) | 2021-10-05 | 2023-04-07 | L'oreal | compositions contenant des teintures directes pour CONFÉRER UNE couleur et UN TON aux cheveux |
FR3128120A1 (fr) | 2021-10-19 | 2023-04-21 | L'oreal | compositions, nécessaires et procédés pour modifier la couleur de fibres kératineuses |
WO2023072944A1 (en) | 2021-10-26 | 2023-05-04 | L'oreal | Process for dyeing and/or lightening keratin fibers |
FR3128377A1 (fr) | 2021-10-26 | 2023-04-28 | L'oreal | Procédé de coloration et/ou d’éclaircissement des fibres kératiniques |
FR3128637A1 (fr) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un tensioactif amphotère ou zwittérionique. |
FR3128633A1 (fr) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un tensioactif amphotère ou zwittérionique. |
FR3128635A1 (fr) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier et deux acides particuliers. |
FR3128634A1 (fr) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un ester d’acide gras et de glycérol. |
FR3128632A1 (fr) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprenant l’association de deux précurseurs de coloration d’oxydation particuliers et un ester d’acide gras et de glycérol. |
FR3128636A1 (fr) | 2021-10-29 | 2023-05-05 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier et deux acides particuliers. |
WO2023073133A1 (en) | 2021-10-29 | 2023-05-04 | L'oreal | Composition comprising a combination of two particular oxidation dye precursors, an amphoteric or zwitterionic surfactant and a solid fatty substance |
WO2023073130A1 (en) | 2021-10-29 | 2023-05-04 | L'oreal | Composition comprising the combination of two particular oxidation dye precursors and a fatty acid ester of glycerol |
WO2023073136A1 (en) | 2021-10-29 | 2023-05-04 | L'oreal | Composition comprising a particular oxidation dye precursor and two particular acids |
WO2023073131A2 (en) | 2021-10-29 | 2023-05-04 | L'oreal | Composition comprising the combination of two particular oxidation dyeing precursors, an amphoteric or zwitterionic surfactant and a solid fatty substance |
WO2023073128A1 (en) | 2021-10-29 | 2023-05-04 | L'oreal | Composition comprising a specific oxidation dye precursor and two specific acids |
WO2023073135A1 (en) | 2021-10-29 | 2023-05-04 | L'oreal | Composition comprising a combination of two particular oxidation dye precursors and a fatty acid ester of glycerol |
US11839678B2 (en) | 2021-11-30 | 2023-12-12 | L'oreal | Compositions, methods, and kits for altering the color of hair |
WO2023102011A1 (en) | 2021-11-30 | 2023-06-08 | Jasmine Martich | Compositions, methods, and kits for altering the color of hair |
WO2023106218A1 (en) | 2021-12-08 | 2023-06-15 | L'oreal | Composition for keratin fibers |
FR3130144A1 (fr) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier, une silicone aminée particulière et un polyol |
FR3130152A1 (fr) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprenant deux précurseurs de coloration d’oxydation particuliers et un tensioactif phosphorique. |
FR3130142A1 (fr) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprenant deux précurseurs de coloration d’oxydation particuliers et une silicone aminée particulière |
WO2023105016A1 (en) | 2021-12-10 | 2023-06-15 | L'oreal | Composition comprising two particular oxidation dye precursors and a phosphoric surfactant |
WO2023105025A1 (en) | 2021-12-10 | 2023-06-15 | L'oreal | Composition comprising a particular oxidation dye precursor, a particular amino silicone and a polyol |
WO2023105022A1 (en) | 2021-12-10 | 2023-06-15 | L'oreal | Composition comprising two particular oxidation dye precursors and a particular amino silicone |
FR3130150A1 (fr) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier et une silicone aminée particulière |
FR3130151A1 (fr) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier, un alcool gras oxyalkyléné et un polysaccharide. |
WO2023105021A1 (en) | 2021-12-10 | 2023-06-15 | L'oreal | Composition comprising a particular oxidation dye precursor and a particular amino silicone |
WO2023105015A1 (en) | 2021-12-10 | 2023-06-15 | L'oreal | Composition comprising a particular oxidation dye precursor, an oxyalkylenated fatty alcohol and a polysaccharide |
FR3130143A1 (fr) | 2021-12-10 | 2023-06-16 | L'oreal | Composition comprenant un précurseur de coloration d’oxydation particulier et une silicone aminée particulière |
WO2023105019A1 (en) | 2021-12-10 | 2023-06-15 | L'oreal | Composition comprising a particular oxidation dye precursor and a particular amino silicone |
FR3130570A1 (fr) | 2021-12-16 | 2023-06-23 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
WO2023110943A1 (en) | 2021-12-16 | 2023-06-22 | L'oreal | Process for lightening or simultaneously bleaching and dyeing keratin fibres |
FR3130567A1 (fr) | 2021-12-16 | 2023-06-23 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
WO2023110947A1 (en) | 2021-12-16 | 2023-06-22 | L'oreal | Process for lightening or for simultaneously bleaching and dyeing keratin fibres |
WO2023110946A1 (en) | 2021-12-16 | 2023-06-22 | L'oreal | Composition for lightening keratin fibres and process for lightening keratin fibres using this composition |
FR3130568A1 (fr) | 2021-12-16 | 2023-06-23 | L'oreal | Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition |
WO2023110948A1 (en) | 2021-12-16 | 2023-06-22 | L'oreal | Composition for lightening keratin fibres and process for lightening keratin fibres using this composition |
WO2023110950A1 (en) | 2021-12-16 | 2023-06-22 | L'oreal | Composition for lightening keratin fibres and process for lightening keratin fibres using this composition |
WO2023110949A1 (en) | 2021-12-16 | 2023-06-22 | L'oreal | Composition for lightening keratin fibres and process for lightening keratin fibres using this composition |
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FR3130575A1 (fr) | 2021-12-22 | 2023-06-23 | L'oreal | Composition cosmétique comprenant du propane-1,3-diol, un ou plusieurs agents alcalins, un ou plusieurs tensioactifs non ioniques, un ou plusieurs polymères acryliques anioniques non associatifs et un ou plusieurs colorants |
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WO2023247616A1 (en) | 2022-06-22 | 2023-12-28 | L'oreal | Composition for lightening keratin fibres and process for lightening keratin fibres using said composition |
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WO2023247614A1 (en) | 2022-06-22 | 2023-12-28 | L'oreal | Method for the treatment of keratin fibres comprising a pretreatment or post-treatment step |
FR3137835A1 (fr) | 2022-07-15 | 2024-01-19 | L'oreal | Composition pour la coloration des fibres kératineuses |
US12144879B2 (en) | 2022-07-31 | 2024-11-19 | L'oreal | Compositions and methods for altering the color of hair |
WO2024030362A1 (en) | 2022-07-31 | 2024-02-08 | L'oreal | Compositions and methods for altering the color of hair |
US12109287B2 (en) | 2022-07-31 | 2024-10-08 | L'oreal | Compositions and methods for altering the color of hair |
FR3139718A1 (fr) | 2022-09-19 | 2024-03-22 | L'oreal | Compositions et procédés pour modifier la couleur des cheveux. |
FR3139719A1 (fr) | 2022-09-21 | 2024-03-22 | L'oreal | Compositions et procédés de modification de la couleur des cheveux. |
FR3139991A1 (fr) | 2022-09-23 | 2024-03-29 | L'oreal | Compositions et méthodes de modification de la couleur des cheveux. |
FR3140541A1 (fr) | 2022-10-11 | 2024-04-12 | L'oreal | Composition comprenant un colorant d’oxydation, un agent alcalin, une gomme de galactomannane cationique, un acide gras solide particulier et un polymère acrylique anionique |
FR3140542A1 (fr) | 2022-10-11 | 2024-04-12 | L'oreal | Composition comprenant un colorant d’oxydation, un agent alcalin, une gomme de galactomannane cationique et un acide gras particulier |
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WO2024134667A1 (en) | 2022-12-23 | 2024-06-27 | L'oreal | A device comprising oxidative composition for dyeing of keratin fibres |
FR3144512A1 (fr) | 2022-12-29 | 2024-07-05 | L'oreal | Composition comprenant au moins l’acide N,N-dicarboxyméthyl glutamique, au moins un agent colorant, et au moins une amine grasse |
WO2024141615A1 (en) | 2022-12-29 | 2024-07-04 | L'oreal | Composition comprising at least n,n-dicarboxymethylglutamic acid, at least one colouring agent and at least one fatty amine |
FR3145686A1 (fr) | 2023-02-10 | 2024-08-16 | L'oreal | Produit de teinture des fibres kératineuses et procédés associés |
FR3145870A1 (fr) | 2023-02-20 | 2024-08-23 | L'oreal | Dispositif comprenant une composition oxydative pour la teinture des fibres kératineuses |
FR3146068A1 (fr) | 2023-02-27 | 2024-08-30 | L'oreal | Composition de colorant pour la teinture des fibres de kératine et nécessaire de teinture contenant celle-ci |
FR3147715A1 (fr) | 2023-04-14 | 2024-10-18 | L'oreal | Composition comprenant au moins un alkyl(poly)glycoside, de l’huile de babassu, au moins un agent alcalin et au moins un colorant d’oxydation. |
FR3147711A1 (fr) | 2023-04-14 | 2024-10-18 | L'oreal | Composition comprenant de l’acide N,N-dicarboxyméthyl glutamique, de l’huile de babassu, au moins un agent alcalin et au moins un colorant d’oxydation. |
FR3147710A1 (fr) | 2023-04-14 | 2024-10-18 | L'oreal | Composition comprenant au moins un acide gras liquide, de l’huile de babassu, au moins un agent alcalin et au moins un colorant d’oxydation. |
Also Published As
Publication number | Publication date |
---|---|
EP0786244A1 (de) | 1997-07-30 |
EP0786244B1 (de) | 2001-09-19 |
DE59607717D1 (de) | 2001-10-25 |
BR9605695A (pt) | 1998-08-18 |
ES2105997T1 (es) | 1997-11-01 |
JPH09143041A (ja) | 1997-06-03 |
JP3657707B2 (ja) | 2005-06-08 |
ES2105997T3 (es) | 2002-03-01 |
US5766576A (en) | 1998-06-16 |
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