DE4133957A1 - Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate - Google Patents

Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate

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Publication number
DE4133957A1
DE4133957A1 DE4133957A DE4133957A DE4133957A1 DE 4133957 A1 DE4133957 A1 DE 4133957A1 DE 4133957 A DE4133957 A DE 4133957A DE 4133957 A DE4133957 A DE 4133957A DE 4133957 A1 DE4133957 A1 DE 4133957A1
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Prior art keywords
amino
hair
pyrazolo
tetrahydro
pyrimidine
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Hans Prof Dr Neunhoeffer
Stefan Gerstung
Thomas Dr Clausen
Wolfgang R Dr Balzer
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Procter and Gamble Deutschland GmbH
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Wella GmbH
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Priority to DE4133957A priority Critical patent/DE4133957A1/de
Priority to EP92917565A priority patent/EP0562061B1/de
Priority to PCT/EP1992/001887 priority patent/WO1993007849A1/de
Priority to US08/027,171 priority patent/US5380340A/en
Priority to ES92917565T priority patent/ES2058040T3/es
Priority to DE59207951T priority patent/DE59207951D1/de
Priority to BR9205395A priority patent/BR9205395A/pt
Publication of DE4133957A1 publication Critical patent/DE4133957A1/de
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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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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

Description

Gegenstand der Erfindung sind Mittel zur oxidativen Färbung von Keratinfasern auf Basis von Aminopyrazol­ derivaten sowie neue Pyrazolderivate.
Auf dem Gebiet der Haarfärbung haben Oxidationsfarb­ stoffe eine wesentliche Bedeutung erlangt. Die Färbung entsteht hierbei durch Reaktion bestimmter Entwickler­ substanzen mit bestimmten Kupplersubstanzen in Gegen­ wart eines geeigneten Oxidationsmittels.
Als Entwicklersubstanzen werden insbesondere 2,5-Diami­ notoluol, 2,5-Diaminophenylethylalkohol, p-Aminophenol und 1,4-Diaminobenzol eingesetzt. Von den vorzugsweise verwendeten Kupplersubstanzen sind Resorcin, 4-Chlor­ resorcin, 1-Naphthol, 5-Amino-2-methylphenol und Deri­ vate des m-Phenylendiamins zu nennen.
An Oxidationsfarbstoffe, die zur Färbung menschlicher Haare verwendet werden, sind zahlreiche besondere An­ forderungen gestellt. So müssen sie in toxikologischer und dermatologischer Hinsicht unbedenklich sein und Färbungen in der gewünschten Intensität ermöglichen. Ferner wird für die erzielten Haarfärbungen eine gute Licht-, Dauerwell-, Säure- und Reibechtheit gefordert. Auf jeden Fall aber müssen solche Haarfärbungen ohne Einwirkung von Licht, Reibung und chemischen Mitteln über einen Zeitraum von mindestens 4 bis 8 Wochen sta­ bil bleiben. Außerdem ist es erforderlich, daß durch Kombinationen geeigneter Entwickler- und Kupplerkompo­ nenten eine breite Palette verschiedener Farbnuancen erzeugt werden kann. Zur Erzielung natürlicher und ins­ besondere modischer Nuancen im Rotbereich wird vor al­ lem 4-Aminophenol, allein oder im Gemisch mit anderen Entwicklersubstanzen, in Kombination mit geeigneten Kupplersubstanzen eingesetzt.
Gegen den für den Rotbereich der Farbskala bisher hauptsächlich eingesetzten Entwickler 4-Aminophenol wurden in letzter Zeit Bedenken in bezug auf die phy­ siologische 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 Pyrazolderivate, wie zum Beispiel das 3-Amino-1-phenyl-2-pyrazolon-5, färben Haare nur in sehr geringen, für die Haarfärbepraxis unbrauchbaren, Farbtiefen an.
Die in der DE-OS 38 43 893 beschriebenen 4,5-Diamino­ pyrazole erfüllen zwar die im Hinblick auf Farbintensi­ tät geforderten Ansprüche, besitzen aber noch Nachtei­ le, die eine Verwendung als Haarfarbstoffe erschweren. So zeigt z. B. das 3(5),4-Diaminopyrazol ein leicht sensibilisierendes Potential. Andere Verbindungen, wie das 4,5-Diamino-1-methyl-pyrazol oder das 4,5-Diamino- 1-benzyl-pyrazol sind nur aufwendig herzustellen, da im Verlauf der Synthese Isomerengemische anfallen, welche chromatographisch aufgetrennt werden müssen.
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 gut verträglich ist, einfach herzustellen ist und welche mit üblichen Kupplersub­ stanzen 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 Ent­ wicklersubstanz-Kupplersubstanz-Kombination, welches als Entwicklersubstanz ein Aminopyrazolderivat der all­ gemeinen Formel (I)
in der R = Wasserstoff oder (C1-C4)-Alkyl bedeutet und n = 2 oder 3 ist oder dessen physiologisch verträg­ liche, wasserlösliche Salze enthält, die gestellte Auf­ gabe in hervorragender Weise gelöst wird.
In den Haarfärbemitteln sollen die Entwicklersubstanzen der Formel (I), von denen das 3-Amino-4,5,8,7-tetrahy­ dro-pyrazolo[1,5-a]pyrimidin (R=H, n=3), das 7-Ami­ no-2,3-dihydro-1H-imidazo[1,2-b]pyrazol (R = H, n = 2) und das 3-Amino-8-methyl-4,5,8,7-tetrahydro-pyrazolo- [1,5-a]pyrimidin (R = CH3, n=3) bevorzugt sind, in einer Menge von 0,01 bis 3,0 Gewichtsprozent, vorzugs­ weise in einer Menge von 0,1 bis 2,5 Gewichtsprozent, enthalten sein.
Obwohl die vorteilhaften Eigenschaften der hier be­ schriebenen neuen Entwicklersubstanzen es nahelegen, diese als alleinige Entwicklersubstanz zu verwenden, ist es selbstverständlich auch möglich, die Entwickler­ substanzen der Formel (I) gemeinsam mit bekannten Ent­ wicklersubstanzen, wie zum Beispiel 1,4-Diaminobenzol, 2,5-Diaminotoluol oder 2,5-Diaminophenylethylalkohol, einzusetzen.
Als Kupplersubstanzen kommen als Bestandteil des hier beschriebenen Haarfärbemittels vorzugsweise Resorcin, 4-Chlorresorcin, 4,8-Dichlorresorcin, 2-Methylresorcin, 2-Amino-4-(2′-hydroxyethyl)amino-anisol, 2,4-Diamino­ benzylalkohol, 2,4-Diaminophenylethylalkohol, m-Pheny­ lendiamin, 2,4-Diamino-5-(2′-hydroxyethoxy)toluol, 5-Amino-2-methylphenol, 5-Amino-4-fluor-2-methylphenol, 5-Amino-2-ethyl-4-fluorphenol, 5-Amino-4-methoxy-2-me­ thylphenol, 2,4-Diaminophenoxyethanol, 4-Amino-2-hydro­ xyphenoxyethanol, 1-Naphthol, 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-Diaminophenetol, 2,4-Diamino-5-methylphenetol, 4-Hydroxyindol, 3-Amino- 5-hydroxy-2,6-dimethoxypyridin und 3,5-Diamino-2,6-di­ methoxypyridin 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 Entwicklerkomponente diesbezüglich in einem gewissen Überschuß oder Unterschuß vorhanden ist.
Weiterhin kann das erfindungsgemäße Haarfärbemittel zusätzlich andere Farbkomponenten, beispielsweise 8-Amino-2-methyl-phenol und 2-Amino-5-methylphenol, sowie ferner übliche direktziehende Farbstoffe, zum Beispiel Triphenylmethanfarbstoffe wie Diamond Fuchsine (C.I. 42 510) und Leather Ruby HF (C.I. 42 520), aroma­ tische Nitrofarbstoffe wie 2-Nitro-1,4-diaminobenzol, 2-Amino-4-nitrophenol, 2-Amino-5-nitrophenol, 2-Amino- 4,6-dinitrophenol, 2-Amino-5-(2′-hydroxyethyl)amino­ nitrobenzol und 2-Methylamino-5-bis(2′-hydroxyethyl)- amino-nitrobenzol, Azofarbstoffe wie Acid Brown 4 (C.I. 14 805) und Dispersionsfarbstoffe wie beispiels­ weise 1,4-Diaminoanthrachinon und 1,4,5,8-Tetraamino­ anthrachinon enthalten. Das Haarfärbemittel kann 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, Isopropanol, Glycerin, oder Glykole wie 1,2- Propylenglykol, weiterhin Netzmittel oder Emulgatoren aus den Klassen der anionischen, kationischen, ampho­ teren oder nichtionogenen oberflächenaktiven Substanzen wie Fettalkoholsulfate, oxethylierte Fettalkohol­ sulfate, Alkylsulfonate, Alkylbenzolsulfonate, Alkyl­ trimethylammoniumsalze, Alkylbetaine, oxethylierte Fettalkohole, oxethylierte Nonylphenole, Fettsäurealka­ nolamide, oxethylierte Fettsäureester, ferner Verdicker wie höhere Fettalkohole, Stärke, Cellulosederivate, Vaseline, Paraffinöl und Fettsäuren sowie außerdem Pflegestoffe wie kationische Harze, Lanolinderivate, Cholesterin, Pantothensäure und Betain. Die erwähnten Bestandteile werden in den für solche Zwecke üblichen Mengen verwendet, zum Beispiel die Netzmittel und Emul­ gatoren 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, normal oder alkalisch reagieren. Insbesondere weist es einen pH-Wert von 8,0 bis 11,5 auf, wobei die Einstellung vorzugsweise mit Ammoniak erfolgt. Es können aber auch organische Amine, zum Beispiel Monoethanolamin und Triethanolamin, oder auch organische Basen wie Natriumhydroxid und Kalium­ hydroxid Verwendung finden.
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 12prozentigen, vorzugsweise 6 prozentigen, wäßrigen Lösung in Betracht. Wird eine 6prozentige Wasserstoffperoxid- Lösung als Oxidationsmittel verwendet, so beträgt das Gewichtsverhältnis zwischen Haarfärbemittel und Oxidationsmittel 5 : 1 bis 1 : 2, vorzugsweise jedoch 1 : 1.
Größere Mengen an Oxidationsmittel werden vor allem bei höheren Farbstoffkonzentrationen im Haarfärbemittel oder wenn gleichzeitig eine stärkere Bleichung des Haares beabsichtigt ist, verwendet. Man läßt das Gemisch bei 15 bis 30 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 Herstellung der erfindungsgemäßen Entwickler­ substanzen ist in der Literatur noch nicht beschrieben.
Die Herstellung von 7-Nitro-2,3-dihydro-1H-imidazo- (1,2-b)pyrazol ist bei A. J. Goddard et al., Anti Cancer Drug Design 2, 235 (1987) beschrieben. Ausgangspunkt ist dort ein 5-Amino-4-cyano-1-(2′-hydroxyethyl)pyra­ zol, aus dem nach Ringschluß und anschließender Nitrie­ rung die gewünschte Verbindung in einer Ausbeute von etwa 10% erhalten wird.
Bessere Ausbeuten wurden dagegen durch Alkylierung mit Dibromalkanen und anschließende Reduktion der Nitro­ gruppe des bei H. Dorn et al., Liebigs-Ann. Chem. 707, (1967) 141-146 beschriebenen 3(5)-Amino-4-nitropyra­ zols erhalten.
Die erfindungsgemäßen Verbindungen lassen sich analog zu den vorstehend beschriebenen Verfahren herstellen.
Die Entwicklersubstanzen der Formel (I) sollen in dem Haarfärbemittel entweder als freie Basen oder in Form ihrer physiologisch verträglichen Salze mit anorgani­ schen oder organischen Säuren, wie zum Beispiel Salz­ säure, Schwefelsäure, Phosphorsäure, Essigsäure, Pro­ pionsäure, Milchsäure oder Zitronensäure, eingesetzt werden. Die Verbindungen der Formel (I) sind gut in Wasser löslich, sie weisen außerdem eine ausgezeichnete Lagerstabilität, insbesondere als Bestandteil der hier beschriebenen Haarfärbemittel auf.
Das erfindungsgemäße Haarfärbemittel mit einem Gehalt an Aminopyrazolderivaten als Entwicklersubstanz ermög­ licht Haarfärbungen mit ausgezeichneter Farbechtheit, insbesondere was die Licht-, Wasch- und Reibechtheit anbetrifft, und die Haarfärbungen lassen sich mit Reduktionsmitteln wieder abziehen.
Hinsichtlich der färberischen Eigenschaften bieten die erfindungsgemäßen Haarfärbemittel Möglichkeiten, die weit über einen Ersatz der üblicherweise verwendeten 4-Aminophenole hinausgehen. So lassen sich brillante Rottöne 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 Entwicklungs­ komponente 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 neue Pyrazolderivate der allgemeinen Formel (II),
in der R1 Wasserstoff oder (C1-C4)-Alkyl bedeutet, n = 2 oder 3 ist und X eine Nitro- oder Aminogruppe darstellt, wobei insbesondere 7-Amino-2,3-dihydro-1H- imidazo[1,2-b]pyrazol, 3-Nitro-4,5,6,7-tetrahydro-pyra­ zolo[1,5-a]pyrimidin, 3-Amino-4,5,6,7-tetrahydro- pyrazolo[1,5-a]pyrimidin, 3-Nitro-6-methyl-4,5,6,7- tetrahydro-pyrazolo [1,5-a]pyrimidin und 3-Amino-6- methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin zu nennen sind.
In den nachstehenden Beispielen soll der Gegenstand der Erfindung näher erläutert werden.
Herstellungsbeispiele Beispiel 1: Herstellung von 3-Amino-4,5,6,7-tetrahydro- pyrazolo[1,5-a]Pyrimidin Stufe 1: Synthese von 3-Nitro-4,5,6,7-tetrahydro-pyra­ zolo[1,5-a]pyrimidin
Zu einer Suspension von 10 g (0,4 mol) Natriumhydrid in 200 ml getrocknetem DMF tropft man langsam eine Lösung von 51,2 g (0,4 mol) 3-Amino-4-nitro-pyrazol in 650 ml getrocknetem DMF. Nach Beendigung der Reaktion werden 121 g (0,6 mol) 1,3-Dibrompropan in 250 ml DMF zugege­ ben. Anschließend wird das Gemisch 5 Stunden lang unter Rückfluß erhitzt. Nach dem Abkühlen wird der Ansatz bis zur Trockene eingeengt. Beim Versetzen des Rückstandes mit 300 ml Dichlormethan und anschließendem Abkühlen auf 0°C fällt das Produkt zusammen mit NaBr aus. Das Rohprodukt wird aus 1200 ml Ethanol umkristallisiert. Dabei werden 59 g (38%) ockerfarbene Kristalle mit einem Schmelzpunkt von 251-252°C erhalten.
¹H-NMR (DMSO-d₆, 60 MHz): = 7,89 (s, 1H, -NH, tauscht mit D₂O aus), 7,85 (s, 1H, 3-H), 3,99 (t, 2H, J = 7 Hz, 1N-CH₂-), 3,35 (mm, 2H, -NH-CH₂-CH₂) und 2,03 ppm (m, 2H, -CH₂-CH₂-CH₂).
MS (70 eV): m/3 = 168 (M⁺)
Stufe 2: Snyhtese von 3-Amino-4,5,6,7-tetrahydropyra­ zolo[1,5-a]pyrimidin
0,6 g (3,57 mmol) 3-Nitro-4,5,6,7-tetrahydropyrazolo [1,5-a]pyrimidin werden in 130 ml Methanol mit 0,1 g Pd/C (10 prozentig) 2 Tage lang bei 25°C und 50 bar hydriert. Nach dem Abfiltrieren des Katalysators wird das Filtrat mit methanolischer HCl versetzt und einge­ engt. Das ausgefallene Produkt wird abgesaugt und mit wenig Methanol gewaschen. Die Verbindung liegt in Form des Trihydrochlorid-Hydrats, welches einen Schmelzpunkt von 179-182°C aufweist, vor. Wird nach dem Abfiltrie­ ren des Katalysators das Filtrat mit einer äquimolaren Menge Schwefelsäure versetzt, erhält man nach der Auf­ arbeitung die Verbindung in Form des Sulfats mit einem Schmelzpunkt von 176-179°C.
¹H-NMR (DMSO-d₆, 60 MHz): = 9,50 (s, breit, 8H, NH₂, HCl, H₂O tauscht mit D₂O aus), 7,75 (s, 1H, 3-H), 4,10 (t, 2H, J = 7 Hz, 1N-CH₂), 3,29 (t, 2H, J = 7, NH-CH₂-CH₂) und 2,02 ppm (m, 2H, -CH₂-CH₂-CH₂).
MS (70 eV): m/e = 138 (M⁺)
Beispiel 2: Herstellung von 7-Amino-2,3-dihydro-1H- imidazo[1,2-b]pyrazol-hydrosulfat
0,15 g (0,97 mmol) 3-Nitro-2,3-dihydro-1H-imidazo[1,2-b] pyrazol werden wie in Beispiel 1, Stufe 2 hydriert.
Nach dem Abfiltrieren des Katalysators wird eine äqui­ molare Menge Schwefelsäure zugegeben. Nach dem Einengen und Versetzen mit wenig Ethanol fällt das Produkt in Form beiger Kristalle mit einem Schmelzpunkt von 177-179°C aus.
¹H-NMR (DMSO-d₆, 60 MHz): = 7,70 (s, breit 5H, NH, NH₂, H₂SO₄, tauscht mit D₂O aus), 7,30 (s, 1H, 3-H) und 4,00 ppm (m, 4H, -CH₂-CH₂-)
MS (70 eV): m/e = 124 (M⁺)
Beispiel 3: Herstellung von 3-Amino-6-methyl-4,5,6,7- tetrahydropyrazolo[1,5-a]pyrimidin Stufe 1: Synthese von 3-Nitro-6-methyl-4,5,6,7-tetra­ hydropyrazolo[1,5-a]pyrimidin
Die Durchführung der Reaktion erfolgt analog Beispiel 1, Stufe 1 mit 1-Brom-3-chlor-2-methylpropan als Alky­ lierungsmittel. Man erhält gelbe Kristalle mit einem Schmelzpunkt von 190-192°C in einer Ausbeute von 25%.
1H-NMR (DMSO-d₆, 60 mH): = 7,92 (s, 1H, -NH, tauscht mit D₂O aus), 7,84 (s, 1H, 2-CH), 4,07 (m, 1H, N-CH₂-), 3,59 (m, 1H, N-CH₂), 3,38 (m, 1H, N-CH₂-), 2,98 (m, 1H, NH-CH₂), 2,20 (m, 1H, 6C-H) und 1,02 ppm (d, 3H, J = 7 Hz, 6C-CH₃).
MS (70 eV): m/e = 182 (M⁺).
Stufe 2: Synthese von 3-Amino-6-methyl-4,5,6,8-tetra­ hydropyrazolo[1,5-a]pyrimidin-sulfat
Entsprechend Beispiel 1, Stufe 2 erhält man nach kata­ lytischer Reduktion und Versetzen des Reaktions­ gemisches mit Schwefelsäure das Sulfat mit einem Schmelzpunkt von 170°C in Form farbloser Kristalle, in einer Ausbeute von 88 Prozent.
1H-NMR (DMSO-d₆, 60 mHz): = 7,40 ppm (s, 5H, NH₂, NH, H₂SO₄ (tauscht mit D₂O aus), 7,23 (s, 1H, 2C-H), 4,25-1,80 (m, 5H, -CH₂CH-CH₂), 0,97 ppm (d, J = 7 Hz, 6C-CH₃)
MS (70 eV): m/e = 152 (M⁺)
Beispiele für Haarfärbemittel Beispiel 3: Haarfärbemittel in Gelform
  1,00 g 3-Amino-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin-sulfat
  0,50 g 5-Amino-2-methylphenol
  0,15 g Natriumsulfit, wasserfrei
  5,00 g Laurylalkohol-diglykolethersulfat-Natriumsalz (28prozentige wäßrige Lösung)
  1,00 g Hydroxyethylcellulose, hochviskos
 10,00 g Ammoniak (22prozentige wäßrige Lösung)
 82,35
g Wasser
100,00 g
50 g des vorstehenden Haarfärbemittels werden kurz vor dem Gebrauch mit 50 g Wasserstoffperoxidlösung (6prozentig) vermischt und das Gemisch anschließend auf blonde Naturhaare aufgetragen. Nach einer Einwirkungs­ zeit von 30 Minuten bei 40 Grad Celsius wird das Haar mit Wasser gespült und getrocknet. Das Haar hat eine intensive purpurrote Färbung erhalten.
Beispiel 5: Haarfärbemittel in Gelform
  0,55 g 3-Amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazolhydrosulfat
  0,27 g 3-Aminophenol
  0,30 g Ascorbinsäure
 15,00 g Ölsäure
  7,00 g Isopropanol
 10,00 g Ammoniak (22prozentige wäßrige Lösung)
 66,88
g Wasser
100,00 g
Man vermischt kurz vor dem Gebrauch 50 g dieses Haar­ färbemittels mit 50 g Wasserstoffperoxid-Lösung (6prozentig) und läßt das Gemisch 30 Minuten lang bei 40 Grad Celsius auf weiße menschliche Haare einwirken. Sodann wird das Haar mit Wasser gespült und getrocknet. Das Haar ist in einem rot-violetten Farbton gefärbt.
Beispiel 6: Färbemittel in Gelform
  1,05 g 3-Amino-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin-sulfat
  0,80 g 2,5-Diaminotoluolsulfat
  1,70 g 2-Amino-4-(2′hydroxyethyl)aminoanisolsulfat
  0,10 g 1-(2′-Ureidoethyl)amino-4-nitrobenzol
  0,15 g Natriumsulfit, wasserfrei
  2,50 g Laurylalkohol-diglykolethersulfat-Natriumsalz (28prozentige wäßrige Lösung)
  0,80 g Hydroxyethylcellulose, hochviskos
  6,00 g Ammoniak (22prozentige wäßrige Lösung)
 86,90
g Wasser
100,00 g
50 g des obigen Haarfärbemittels werden kurz vor dem Gebrauch mit 50 g Wasserstoffperoxid-Lösung (6prozen­ tig) vermischt und die Mischung anschließend auf blonde Naturhaare aufgebracht. Nach einer Einwirkungszeit von 30 Minuten bei 40 Grad Celsius wird mit Wasser gespült und getrocknet. Das Haar hat eine aubergine Färbung erhalten.
Beispiel 7: Haarfärbemittel in Gelform
  1,05 g 3-Amino-6-methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin-sulfat
  0,40 g 5-Amino-2-methylphenol
  0,12 g 3-Aminophenol
  0,15 g Natriumsulfit, wasserfrei
  5,00 g Laurylalkohol-diglykolethersulfat-Natriumsalz (28prozentige wäßrige Lösung)
  1,00 g Hydroxyethylcellulose, hochviskos
 10,00 g Ammoniak (22prozentige wäßrige Lösung)
 82,28
g Wasser
100,00 g
50 g des vorstehenden Haarfärbemittels werden kurz vor dem Gebrauch mit 50 g Wasserstoffperoxidlösung (6prozentig) vermischt und das Gemisch anschließend auf blonde Naturhaare aufgetragen. Nach einer Einwirkungs­ zeit von 30 Minuten bei 40 Grad Celsius wird das Haar mit Wasser gespült und getrocknet. Die Haare sind in einem intensiven Bordeaux-Ton gefärbt.

Claims (12)

1. Mittel zur oxidativen Färbung von Haaren auf der Basis einer Entwicklersubstanz-Kupplersubstanz- Kombination, dadurch gekennzeichnet, daß es als Entwicklersubstanz ein Aminopyrazolderivat der allgemeinen Formel (I), in der R = Wasserstoff oder (C1-C4)-Alkyl bedeutet und n=2 oder 3 ist, oder dessen physio­ logisch verträgliche wasserlösliche Salze enthält.
2. Mittel nach Anspruch 1, dadurch gekennzeichnet, daß das Aminopyrazol-Derivat der Formel (I) ausgewählt ist aus 3-Amino-4,5,6,7-tetrahydro- pyrazolo[1,5-a]pyrimidin, 7-Amino-2,3-dihydro-1H- imidazo[1,2-b]pyrazol oder 3-Amino-6-methyl- 4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin.
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 Gewichts­ prozent enthalten ist.
4. Mittel nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß die Kupplersubstanz ausgewählt ist aus Resorcin, 4-Chlorresorcin, 4,6-Dichlor­ resorcin, 2-Methylresorcin, 2-Amino-4-(2′-hydro­ xyethyl)amino-anisol, 2,4-Diaminobenzylalkohol, 2,4-Diaminophenylethylalkohol, m-Phenylendiamin, 2,4-Diamino-5-(2′-hydroxyethoxy)toluol, 5-Amino- 2-methylphenol, 5-Amino-4-fluor-2-methylphenol, 5-Amino-2-ethyl-4-fluorphenol, 5-Amino-4-methoxy- 2-methylphenol, 2,4-Diaminophenoxyethanol, 4-Ami­ no-2-hydroxyphenoxyethanol, 1-Naphthol, 3-Amino- phenol, 3-Amino-2-methylphenol, 4-Hydroxy-1,2- methylendioxybenzol, 4-Amino-1,2-methylendioxy­ benzol, 4-(2′-Hydroxyethyl)amino-1,2-methylen­ dioxybenzol, 2,4-Diaminophenetol, 2,4-Diamino­ 5-methylphenetol, 4-Hydroxyindol, 3-Amino-5-hy­ droxy-2,6-dimethoxypyridin und 3,5-Diamino-2,6- dimethoxypyridin.
5. Mittel nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß die Gesamtmenge der Entwick­ ler-Kupplersubstanz-Kombination 0,1 bis 5,0 Gewichtsprozent, vorzugsweise 0,5 bis 4,0 Gewichtsprozent, beträgt.
6. Mittel nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß es eine Farbkomponente ent­ hält, die ausgewählt ist aus 6-Amino-2-methyl­ phenol, 2-Amino-5-methylphenol, Diamond Fuchsine (C.I. 42 510), Leather Ruby HF (C.I. 42 520), 2-Nitro-1,4-diaminobenzol, 2-Amino-4-nitrophenol, 2-Amino-5-nitrophenol, 2-Amino-4,6-dinitrophenol, 2-Amino-5-(2′-hydroxyethyl)amino-nitrobenzol, 2-Methylamino-5-bis(2′-hydroxyethyl)amino-nitro­ benzol, Acid Brown 4 (C.I. 14 805), 1,4-Diamino­ anthrachinon und 1,4,5,8-Tetraaminoanthrachinon.
7. Pyrazolderivat der allgemeinen Formel (II), in der R1=Wasserstoff oder (C1-C4)-Alkyl bedeutet, n = 2 oder 3 ist und X eine Nitro- oder Aminogruppe darstellt.
8. 7-Amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazol
9. 3-Nitro-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin
10. 3-Amino-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyramidin
11. 3-Nitro-6-methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrimidin
12. 3-Amino-6-methyl-4,5,6,7-tetrahydro-pyrazolo [1,5-a]pyrimidin.
DE4133957A 1991-10-14 1991-10-14 Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate Withdrawn DE4133957A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE4133957A DE4133957A1 (de) 1991-10-14 1991-10-14 Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
EP92917565A EP0562061B1 (de) 1991-10-14 1992-08-19 Haarfärbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
PCT/EP1992/001887 WO1993007849A1 (de) 1991-10-14 1992-08-19 Haarfärbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
US08/027,171 US5380340A (en) 1991-10-14 1992-08-19 Hair dye containing aminopyrazole derivatives as well as pyrazole derivatives
ES92917565T ES2058040T3 (es) 1991-10-14 1992-08-19 Colorante para teñir el cabello con un contenido en derivados del amino-pirazol y nuevos derivados del pirazol.
DE59207951T DE59207951D1 (de) 1991-10-14 1992-08-19 Haarfärbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
BR9205395A BR9205395A (pt) 1991-10-14 1992-08-19 Agentes para o tingimento de cabelos com um teor de derivados de aminopirazol, bem como novos derivados de pirazol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE4133957A DE4133957A1 (de) 1991-10-14 1991-10-14 Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate

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DE4133957A1 true DE4133957A1 (de) 1993-04-15

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DE4133957A Withdrawn DE4133957A1 (de) 1991-10-14 1991-10-14 Haarfaerbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate
DE59207951T Expired - Lifetime DE59207951D1 (de) 1991-10-14 1992-08-19 Haarfärbemittel mit einem gehalt an aminopyrazolderivaten sowie neue pyrazolderivate

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US (1) US5380340A (de)
EP (1) EP0562061B1 (de)
BR (1) BR9205395A (de)
DE (2) DE4133957A1 (de)
ES (1) ES2058040T3 (de)
WO (1) WO1993007849A1 (de)

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FR3115987A1 (fr) 2020-11-06 2022-05-13 L'oreal Composition pour fibres kératineuses
FR3116199A1 (fr) 2020-11-17 2022-05-20 L'oreal Composition pour fibres kératineuses
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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
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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
WO2022129349A1 (en) 2020-12-17 2022-06-23 L'oreal Dyeing composition based on 2-gamma-hydroxypropyl-para-phenylenediamine and a phosphoric surfactant
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
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
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
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
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WO2022238545A1 (en) 2021-05-12 2022-11-17 L'oreal Device for the oxidation dyeing of keratin fibres
WO2023275198A1 (en) 2021-06-30 2023-01-05 L'oreal Composition comprising an alkanolamine, a (meta)silicate, glycine, a dye and a polysaccharide
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
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
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
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
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
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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
WO2023275187A1 (en) 2021-06-30 2023-01-05 L'oreal Composition comprising shea, an alkyl(poly)glycoside, a polysaccharide and a dye
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
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
WO2023275170A1 (en) 2021-06-30 2023-01-05 L'oreal Composition comprising at least one alkanolamine, a (meta)silicate, glycine and 1,3-propanediol
WO2023278726A1 (en) 2021-06-30 2023-01-05 L'oreal Compositions containing direct dyes for imparting color and tone to the hair
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
FR3124721A1 (fr) 2021-06-30 2023-01-06 L'oreal Un kit de teinture
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.
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.
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.
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.
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
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
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
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.
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.
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FR3127131A1 (fr) 2021-09-17 2023-03-24 L'oreal Compositions pour CONFÉRER UNE couleur et UN TON aux cheveux
FR3127130A1 (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
FR3128377A1 (fr) 2021-10-26 2023-04-28 L'oreal Procédé de coloration et/ou d’éclaircissement des fibres kératiniques
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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
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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
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
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
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WO2023105016A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising two particular oxidation dye precursors and a phosphoric surfactant
WO2023105015A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising a particular oxidation dye precursor, an oxyalkylenated fatty alcohol and a polysaccharide
WO2023105021A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising a particular oxidation dye precursor and a particular amino silicone
WO2023105022A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising two particular oxidation dye precursors and a particular amino silicone
WO2023105025A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising a particular oxidation dye precursor, a particular amino silicone and a polyol
WO2023105019A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising a particular oxidation dye precursor and a particular amino silicone
WO2023110943A1 (en) 2021-12-16 2023-06-22 L'oreal Process for lightening or simultaneously bleaching and dyeing keratin fibres
WO2023110950A1 (en) 2021-12-16 2023-06-22 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using this composition
WO2023110947A1 (en) 2021-12-16 2023-06-22 L'oreal Process for lightening or for simultaneously bleaching and dyeing keratin fibres
WO2023110949A1 (en) 2021-12-16 2023-06-22 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using this composition
WO2023110946A1 (en) 2021-12-16 2023-06-22 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using this 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
FR3130580A1 (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 polymères cellulosiques associatifs et un ou plusieurs colorants
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
FR3130582A1 (fr) 2021-12-22 2023-06-23 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre une composition cosmétique comprenant du propane-1,3-diol et une composition colorante
FR3130577A1 (fr) 2021-12-22 2023-06-23 L'oreal Composition comprenant deux polyols différents l’un de l’autre, un agent alcalin et un colorant
FR3131695A1 (fr) 2022-01-12 2023-07-14 L'oreal Composition comprenant au moins un tensioactif anionique, une silicone particulière et un agent oxydant chimique
FR3131696A1 (fr) 2022-01-13 2023-07-14 L'oreal Composition pour fibres kératiniques
US11701311B2 (en) 2018-06-20 2023-07-18 L'oreal Device for dispensing a hair dyeing product using a dye composition and an oxidizing composition comprising a scleroglucan gum
FR3131843A1 (fr) 2022-01-20 2023-07-21 L'oreal Composition de coloration d’oxydation comprenant un tensioactif anionique, un tensioactif amphotere choisi parmi une betaïne et un catalyseur metallique
FR3132635A1 (fr) 2022-02-17 2023-08-18 L'oreal compositions, procédés et nécessaires pour modifier la couleur des cheveux
WO2023164307A1 (en) 2022-02-28 2023-08-31 Rughani Ronak Compositions and methods for hair
FR3134719A1 (fr) 2022-04-26 2023-10-27 L'oreal compositions et procédés pour le traitement des cheveux
US11826451B2 (en) 2019-12-31 2023-11-28 L'oreal Compositions for treating hair
WO2023228870A1 (en) 2022-05-25 2023-11-30 L'oreal Composition for coloring keratin fibers
US11839678B2 (en) 2021-11-30 2023-12-12 L'oreal Compositions, methods, and kits for altering the color of hair
WO2023247618A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
WO2023247612A1 (en) 2022-06-22 2023-12-28 L'oreal Process for treating keratin fibres using a carnitine salt or a carnitine derivative
WO2023247617A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
WO2023247615A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
WO2023247610A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
WO2023247616A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
WO2023247614A1 (en) 2022-06-22 2023-12-28 L'oreal Method for the treatment of keratin fibres comprising a pretreatment or post-treatment step
WO2023247620A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
FR3136970A1 (fr) 2022-06-22 2023-12-29 L'oreal Procédé de traitement des fibres kératiniques
FR3136973A1 (fr) 2022-06-22 2023-12-29 L'oreal Procédé de traitement des fibres kératiniques
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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.
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.
FR3117813A1 (fr) 2020-12-17 2022-06-24 L'oreal Composition comprenant l’association d’au moins un corps gras, d’un acide carboxylique particulier et d’un colorant d’oxydation et/ou un agent alcalin
US12390408B2 (en) 2020-12-17 2025-08-19 L'oreal Composition comprising two particular oxidation dye precursors, and a particular carboxylic acid
US12337051B2 (en) 2020-12-17 2025-06-24 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
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.
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
FR3117841A1 (fr) 2020-12-17 2022-06-24 L'oreal Composition comprenant deux précurseurs de coloration d’oxydation particuliers, et un acide carboxylique particulier
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.
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.
US12296035B2 (en) 2020-12-17 2025-05-13 L'oreal Composition comprising a particular oxidation dyeing base, at least one particular coupler and at least one fatty substance
WO2022129389A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dyeing base, at least one particular coupler and at least one fatty substance
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.
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
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
FR3117837A1 (fr) 2020-12-17 2022-06-24 L'oreal Composition comprenant un précurseur de coloration d’oxydation particulier et 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.
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
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.
US12263237B2 (en) 2020-12-17 2025-04-01 L'oreal Composition comprising two particular oxidation dye precursors, an oxyethylenated fatty acid ester of sorbitan and a fatty acid
FR3117827A1 (fr) 2020-12-17 2022-06-24 L'oreal Composition comprenant un précurseur de coloration d’oxydation particulier et un acide carboxylique particulier
WO2022129379A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising two particular oxidation dye precursors, and a particular carboxylic acid
US12178898B2 (en) 2020-12-17 2024-12-31 L'oreal Composition comprising the combination of two particular oxidation dye precursors and a particular oxyethylenated fatty acid ester of sorbitan
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
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
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
US12178899B2 (en) 2020-12-17 2024-12-31 L'oreal Composition comprising the combination of two particular oxidation dye precursors and an alkyl(poly)glycoside
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
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
WO2022129394A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dyeing base and at least two particular couplers
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
WO2022129380A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising a particular oxidation dye precursor and a particular carboxylic acid
WO2022129364A1 (en) 2020-12-17 2022-06-23 L'oreal Composition comprising the combination of three particular oxidation dye precursors
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
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
WO2022129344A1 (en) 2020-12-18 2022-06-23 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using this composition
WO2022129343A1 (en) 2020-12-18 2022-06-23 L'oreal Process for lightening keratin fibres
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
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
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
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
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
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
FR3118707A1 (fr) 2021-01-08 2022-07-15 L'oreal Composition solide pour la teinture et/ou l’éclaircissement des fibres kératineuses
WO2022238545A1 (en) 2021-05-12 2022-11-17 L'oreal Device for the oxidation dyeing of keratin fibres
FR3122814A1 (fr) 2021-05-12 2022-11-18 L'oreal Dispositif pour la coloration d’oxydation des fibres kératiniques
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
FR3124721A1 (fr) 2021-06-30 2023-01-06 L'oreal Un kit de teinture
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.
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
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.
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
WO2023275198A1 (en) 2021-06-30 2023-01-05 L'oreal Composition comprising an alkanolamine, a (meta)silicate, glycine, a dye and a polysaccharide
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.
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
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
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.
FR3124722A1 (fr) 2021-06-30 2023-01-06 L'oreal Composition retardatrice d’oxydation
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
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.
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.
FR3124727A1 (fr) 2021-06-30 2023-01-06 L'oreal Composition comprenant une alcanolamine, un (méta)silicate, la glycine, un colorant et un polysaccharide.
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.
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
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
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.
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
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
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
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
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
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
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
US12036299B2 (en) 2021-06-30 2024-07-16 L'oreal Compositions containing direct dyes for imparting color and tone to the hair
US12109289B2 (en) 2021-06-30 2024-10-08 L'oreal Compositions for imparting color and tone to the hair
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
WO2023275187A1 (en) 2021-06-30 2023-01-05 L'oreal Composition comprising shea, an alkyl(poly)glycoside, a polysaccharide and a dye
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
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
WO2023275170A1 (en) 2021-06-30 2023-01-05 L'oreal Composition comprising at least one alkanolamine, a (meta)silicate, glycine and 1,3-propanediol
WO2023278726A1 (en) 2021-06-30 2023-01-05 L'oreal Compositions containing direct dyes for imparting color and tone to the hair
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
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
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
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.
US11707420B2 (en) 2021-08-31 2023-07-25 L'oreal Compositions, kits, and methods for altering the color of hair
WO2023034391A1 (en) 2021-08-31 2023-03-09 L'oreal Compositions, kits, and methods for altering the color of hair
FR3127131A1 (fr) 2021-09-17 2023-03-24 L'oreal Compositions pour CONFÉRER UNE couleur et UN TON aux cheveux
FR3127130A1 (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
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.
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
WO2023073136A1 (en) 2021-10-29 2023-05-04 L'oreal Composition comprising a particular oxidation dye precursor and two particular acids
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
WO2023073128A1 (en) 2021-10-29 2023-05-04 L'oreal Composition comprising a specific oxidation dye precursor and two specific acids
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
FR3128635A1 (fr) 2021-10-29 2023-05-05 L'oreal Composition comprenant un précurseur de coloration d’oxydation particulier et deux acides particuliers.
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.
FR3128636A1 (fr) 2021-10-29 2023-05-05 L'oreal Composition comprenant un précurseur de coloration d’oxydation particulier et deux acides particuliers.
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.
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.
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
WO2023105019A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising a particular oxidation dye precursor and a particular amino silicone
FR3130143A1 (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.
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
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
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
FR3130152A1 (fr) 2021-12-10 2023-06-16 L'oreal Composition comprenant deux précurseurs de coloration d’oxydation particuliers et un tensioactif phosphorique.
WO2023105016A1 (en) 2021-12-10 2023-06-15 L'oreal Composition comprising two particular oxidation dye precursors and a phosphoric surfactant
FR3130150A1 (fr) 2021-12-10 2023-06-16 L'oreal Composition comprenant un précurseur de coloration d’oxydation particulier et une silicone aminée particulière
FR3130142A1 (fr) 2021-12-10 2023-06-16 L'oreal Composition comprenant deux précurseurs de coloration d’oxydation particuliers et une silicone aminée particulière
WO2023110946A1 (en) 2021-12-16 2023-06-22 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using this composition
WO2023110947A1 (en) 2021-12-16 2023-06-22 L'oreal Process for lightening or for simultaneously bleaching and dyeing keratin fibres
FR3130569A1 (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
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
FR3130571A1 (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
FR3130572A1 (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
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
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
WO2023110948A1 (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
WO2023110943A1 (en) 2021-12-16 2023-06-22 L'oreal Process for lightening or simultaneously bleaching and dyeing keratin fibres
WO2023110950A1 (en) 2021-12-16 2023-06-22 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using this composition
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
FR3130582A1 (fr) 2021-12-22 2023-06-23 L'oreal Procédé de coloration des fibres kératiniques mettant en œuvre une composition cosmétique comprenant du propane-1,3-diol et une composition colorante
FR3130577A1 (fr) 2021-12-22 2023-06-23 L'oreal Composition comprenant deux polyols différents l’un de l’autre, un agent alcalin et un colorant
WO2023118332A1 (en) 2021-12-22 2023-06-29 L'oreal Composition comprising two polyols different from one another, an alkaline agent and a dye
FR3130580A1 (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 polymères cellulosiques associatifs et un ou plusieurs colorants
WO2023118333A1 (en) 2021-12-22 2023-06-29 L'oreal Process for dyeing keratin fibres using a cosmetic composition comprising propane-1,3-diol and a dyeing composition
FR3131695A1 (fr) 2022-01-12 2023-07-14 L'oreal Composition comprenant au moins un tensioactif anionique, une silicone particulière et un agent oxydant chimique
FR3131696A1 (fr) 2022-01-13 2023-07-14 L'oreal Composition pour fibres kératiniques
FR3131843A1 (fr) 2022-01-20 2023-07-21 L'oreal Composition de coloration d’oxydation comprenant un tensioactif anionique, un tensioactif amphotere choisi parmi une betaïne et un catalyseur metallique
FR3132635A1 (fr) 2022-02-17 2023-08-18 L'oreal compositions, procédés et nécessaires pour modifier la couleur des cheveux
US12268767B2 (en) 2022-02-28 2025-04-08 L'oreal Compositions and methods for treating hair
WO2023164307A1 (en) 2022-02-28 2023-08-31 Rughani Ronak Compositions and methods for hair
FR3134719A1 (fr) 2022-04-26 2023-10-27 L'oreal compositions et procédés pour le traitement des cheveux
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WO2023247617A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
FR3136966A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
WO2023247615A1 (en) 2022-06-22 2023-12-28 L'oreal Composition for lightening keratin fibres and process for lightening keratin fibres using said composition
FR3136976A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
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FR3136972A1 (fr) 2022-06-22 2023-12-29 L'oreal Composition d’éclaircissement des fibres kératiniques et procédé d’éclaircissement des fibres kératiniques mettant en œuvre cette composition
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US12144879B2 (en) 2022-07-31 2024-11-19 L'oreal Compositions and methods for altering the color of hair
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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.
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
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
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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
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FR3145686A1 (fr) 2023-02-10 2024-08-16 L'oreal Produit de teinture des fibres kératineuses et procédés associés
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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.
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.
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WO2024241333A1 (en) 2023-05-24 2024-11-28 L'oréal Product containing a dye composition comprising a fatty acid, a non-ionic surfactant, a non-associative polymer, at least 10% by weight of one or more fatty substances, a polyol, two specific dye precursors and an oxidizing composition
WO2024241332A1 (en) 2023-05-24 2024-11-28 L'oréal Product containing a dye composition comprising a fatty acid, a non-ionic surfactant, a non-associative polymer, at least 10% by weight of one or more fatty substances, a polyol, a specific dye precursor and an oxidizing composition
FR3150433A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant une glycoprotéine et un agent colorant.
WO2025003363A1 (en) 2023-06-30 2025-01-02 L'oreal Composition comprising hyaluronic acid and/or a derivative thereof, a (bi)carbonate, a fatty acid and a dye
FR3150415A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant un coupleur particulier et du bicarbonate d’ammonium.
FR3150439A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant une cire, un (bi)carbonate, un acide gras, un corps gras et un colorant.
WO2025003366A1 (en) 2023-06-30 2025-01-02 L'oreal Composition comprising a particular coupler ammonium bicarbonate and fatty acid
WO2025003345A1 (en) 2023-06-30 2025-01-02 L'oreal Composition comprising a particular base ammonium bicarbonate and fatty acid
WO2025003368A1 (en) 2023-06-30 2025-01-02 L'oreal Composition comprising a particular polycarboxylic acid or a salt thereof, a (bi)carbonate in a particular content, an additional alkaline agent, a fatty substance and a dye
FR3150434A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant de l’acide hyaluronique et/ou l’un de ses dérivés, un tensioactif anionique, un agent alcalin, un colorant, un alcool gras solide et un alcool gras liquide.
FR3150435A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant de l’acide hyaluronique et/ou l’un de ses dérivés, un (bi)carbonate, un acide gras et un colorant.
FR3150429A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant une base particulière et du bicarbonate d’ammonium.
FR3150428A1 (fr) 2023-06-30 2025-01-03 L'oreal Composition comprenant un acide carboxylique particulier ou l’un de ses sels, un (bi)carbonate dans une teneur particulière, un agent alcalin additionnel, un corps gras et un colorant.
WO2025003347A1 (en) 2023-06-30 2025-01-02 L'oreal Composition comprising hyaluronic acid and/or a derivative thereof, an anionic surfactant, an alkaline agent, a dye, a solid fatty alcohol and a liquid fatty alcohol
FR3151204A3 (fr) 2023-07-21 2025-01-24 L'oreal Produit de coloration de fibres keratiniques humaines et procede de coloration correspondant
FR3151203A3 (fr) 2023-07-21 2025-01-24 L'oreal Produit de coloration de fibres keratiniques humaines et procede de coloration correspondant
FR3151205A3 (fr) 2023-07-21 2025-01-24 L'oreal Produit de teinture de fibres keratineuses humaines comprenant une composition tinctoriale
FR3152389A3 (fr) 2023-08-30 2025-03-07 L'oreal Nécessaire de teinture des fibres de kératine
WO2025069042A1 (en) 2023-09-28 2025-04-03 L'oreal Compositions and methods for dyeing and/or lightening keratin fibres
WO2025069043A1 (en) 2023-09-28 2025-04-03 L'oreal Sustainable compositions and methods for dyeing and/or lightening keratin fibres
FR3155137A3 (fr) 2023-11-10 2025-05-16 L'oreal Composition et procédé de teinture et/ou d’éclaircissement des fibres de kératine
FR3155427A3 (fr) 2023-11-16 2025-05-23 L'oreal Compositions et procédés de teinture et/ou d'éclaircissement des fibres kératineuses
FR3155428A3 (fr) 2023-11-20 2025-05-23 L'oreal Composition de teinture et/ou d’éclaircissement des fibres de kératine, et leurs procédés
WO2025127156A1 (en) 2023-12-15 2025-06-19 L'oreal Composition for keratin fibers
WO2025126227A1 (en) 2023-12-15 2025-06-19 L'oreal A composition for dyeing /lightening of keratin fibres, and methods thereof
WO2025126228A1 (en) 2023-12-15 2025-06-19 L'oreal A composition for dyeing /lightening of keratin fibres
WO2025132607A1 (en) 2023-12-20 2025-06-26 L'oreal Aqueous composition comprising at least one (bi)carbonate and/or (bi)carbonate-generating systems and at least one silicate in a particular ratio
FR3157121A1 (fr) 2023-12-20 2025-06-27 L'oreal Composition aqueuse comprenant au moins un (bi)carbonate et/ou systèmes générateurs de (bi)carbonates et au moins un silicate dans un ratio particulier
FR3158440A3 (fr) 2024-01-19 2025-07-25 L'oreal Composition pour fibres kératineuses
FR3158441A3 (fr) 2024-01-19 2025-07-25 L'oreal Composition pour fibres kératineuses
FR3158884A1 (fr) 2024-02-05 2025-08-08 L'oreal Procédé de coloration comprenant au moins la mise en œuvre d’une composition comprenant au moins un colorant d’oxydation, au moins un agent alcalin, au moins un polymère acrylique anionique et au moins un polyol
WO2025168477A1 (en) 2024-02-05 2025-08-14 L'oreal Composition comprising an oxidation dye, an alkaline agent, a chemical oxidizing agent, an anionic acrylic polymer, a fatty acid, a nonionic surfactant and a fatty substance
FR3158883A1 (fr) 2024-02-05 2025-08-08 L'oreal Composition comprenant au moins un colorant d’oxydation, au moins un agent alcalin, au moins un agent oxydant chimique, au moins un polymère acrylique anionique, au moins un acide gras, au moins un tensioactif non ionique et au moins un corps gras
FR3159514A3 (fr) 2024-02-26 2025-08-29 L'oreal Composition de teinture/d'éclaircissement des fibres de kératine
FR3159513A3 (fr) 2024-02-27 2025-08-29 L'oreal Composition de teinture/d’éclaircissement des fibres de kératine, et procédés associés
FR3159744A3 (fr) 2024-02-29 2025-09-05 L'oreal Composition comprenant un tensioactif cationique spécifique, un polymère amphotère et un agent oxydant et/ou une teinture d’oxydation, et procédé de traitement des cheveux
FR3161858A3 (fr) 2024-05-06 2025-11-07 L'oreal Compositions et procédés de traitement des cheveux

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BR9205395A (pt) 1994-06-21
ES2058040T1 (es) 1994-11-01
DE59207951D1 (de) 1997-03-06
ES2058040T3 (es) 1997-05-16
US5380340A (en) 1995-01-10
EP0562061B1 (de) 1997-01-22
WO1993007849A1 (de) 1993-04-29
EP0562061A1 (de) 1993-09-29

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