DE4220388A1 - Cationic azo dyes - for keratin materials showing improved evenness - Google Patents

Cationic azo dyes - for keratin materials showing improved evenness

Info

Publication number
DE4220388A1
DE4220388A1 DE19924220388 DE4220388A DE4220388A1 DE 4220388 A1 DE4220388 A1 DE 4220388A1 DE 19924220388 DE19924220388 DE 19924220388 DE 4220388 A DE4220388 A DE 4220388A DE 4220388 A1 DE4220388 A1 DE 4220388A1
Authority
DE
Germany
Prior art keywords
dyes
keratin materials
cationic
azo dyes
cationic azo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
DE19924220388
Other languages
German (de)
Inventor
Horst Dipl Chem Noack
Regina Dipl Chem Muehlberg
Bernd Dr Noll
Herbert Dr Weinelt
Heinz-Georg Dipl Chem Bromann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chemie GmbH Bitterfeld Wolfen
Original Assignee
Chemie GmbH Bitterfeld Wolfen
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Filing date
Publication date
Application filed by Chemie GmbH Bitterfeld Wolfen filed Critical Chemie GmbH Bitterfeld Wolfen
Priority to DE19924220388 priority Critical patent/DE4220388A1/en
Publication of DE4220388A1 publication Critical patent/DE4220388A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C09B44/04—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing amino as the only directing group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/18—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having three nitrogen atoms as the only ring hetero atoms

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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)

Abstract

Cationic azo dyes for keratin materials contg. dye and additives are characterised by contg. a cationic monoazo dye of formula (I), where, R1, R2 = methyl or ethyl. USE/ADVANTAGE - The dyes give improved evenness.

Description

Die Erfindung betrifft kationische Monoazofarbstoffe zum Färben von Keratinmaterialien.The invention relates to cationic monoazo dyes Staining keratin materials.

Es ist bekannt, daß zum Färben von Keratinmaterialien kationische Azofarbstoffe verwendet werden. In den US-PS 3869454 und 3985499 sind Farbsalz heterocyclischer p-Aminoazofarbstoffe der FormelIt is known that cationic for coloring keratin materials Azo dyes are used. In U.S. Patent Nos. 3,869,454 and 3,985,499 are color salts of heterocyclic p-aminoazo dyes of the formula

in der X=N oder S bedeuten und A der Rest eines aromatischen Ringes darstellt, beschrieben.in which X = N or S and A is the remainder of an aromatic Ringes described.

Die bevorzugten Heterocyclen sind der Benzthiazol- und der Benz­ imidazolrest.The preferred heterocycles are benzothiazole and benz imidazole residue.

Mit diesen Farbstoffen werden violette und blaue Farbtöne erhal­ ten.With these dyes, violet and blue shades are obtained ten.

Für die Erzielung roter Nuancen sind die kationischen Farbstoffe
CI Basic Red. 22,
CI Basic Red. 29 und
CI Basic Red. 76
bekannt.The cationic dyes are used to achieve red shades
CI Basic Red. 22,
CI Basic Red. 29 and
CI Basic Red. 76
known.

Diese Farbstoffe zeigen jedoch den Nachteil, daß sie ein ungenügendes Ausgleichsvermögen besitzen.However, these dyes have the disadvantage that they are insufficient Have compensation.

Die Aufgabe der Erfindung ist es, rote kationische Farbstoffe mit einem guten Ausgleichsvermögen aufzufinden.The object of the invention is to use red cationic dyes to find a good balance.

Aus der DE-AS 16 44 112 sind kationische Monoazofarbstoffe bekannt, die durch Kupplung von N-Aryl-,N-alkylaminoethyl-N′,N′-dialkyl-, N′-arylammoniumsalzen der FormelCationic monoazo dyes are known from DE-AS 16 44 112, by coupling N-aryl-, N-alkylaminoethyl-N ′, N′-dialkyl-, N'-arylammonium salts of the formula

mit geeigneten Benzendiazoniumverbindungen erhalten werden. Das Hauptanwendungsgebiet der Farbstoffe ist die Färbung von Polyacrylnitrilfasern. Der Einsatz zum Färben von Keratinmateria­ lien ist nicht bekannt. Auf Polyacrylnitril werden intensive Fär­ bungen erzielt. Die Leuchtkraft der Farbstoffe ist jedoch verhält­ nismäßig gering.can be obtained with suitable benzene diazonium compounds. The main application of the dyes is the coloring of Polyacrylonitrile fibers. The use for dyeing keratin matter lien is not known. Intensive color on polyacrylonitrile exercises achieved. However, the luminosity of the dyes is behaving moderately low.

Für glänzende Haarfärbungen werden vorzugsweise Farbstoffe mit hoher Leuchtkraft verwendet.For glossy hair colors, dyes with a high color are preferred Luminosity used.

Aufgabe der Erfindung ist es, rote kationische Farbstoffe mit einem guten Ausgleichsvermögen aufzufinden.The object of the invention is to use red cationic dyes to find a good balance.

Es wurde gefunden, daß die kationischen Farbstoffe der FormelIt has been found that the cationic dyes of the formula

in der
R1und R2 = CH3- und C2H5-Reste bedeuten, wobei R1und R2 gleich oder verschieden sein kann für die Färbung von Keratinmaterialien, insbesondere für die Färbung von Humanhaar geeignet ist.in the
R 1 and R 2 = CH 3 and C 2 H 5 radicals, where R 1 and R 2 may be the same or different for the coloring of keratin materials, in particular for the coloring of human hair.

Die Kupplungskomponenten für die erfindungsgemäßen Farbstoffe können erhalten werden durch Kondensation eines N-Ethyl-N-halogen­ methylanilins mit Dimethyl- oder Diethylanilin oder durch Alkylie­ rung von N,N′-Diphenyl-N-ethyl-,N′-(methyl- oder ethyl)-ethylen­ diamin.The coupling components for the dyes of the invention can be obtained by condensing an N-ethyl-N-halogen methylaniline with dimethyl or diethylaniline or by alkylly tion of N, N'-diphenyl-N-ethyl-, N '- (methyl- or ethyl) -ethylene diamine.

Aus dem Houben-Weyl (IV. Auflage, 1958) Bd. XI, 2, N-Verbindungen, Bd. II/III, Seite 606 ist bekannt, daß die Alkylierung des N,N′-Diphenyl-N,N′-diethylethylendiamins in Abhängigkeit vom Alkylierungsmittel zu unterschiedlichen Produkten führt. Mit Methyljodid als Alkylierungsagenz wird die Methylierung eines tertiären Aminstickstoffs zum N-Methyl-N-ethyl-N-phenyl-N- (N′-ethyl-N′-phenylaminoethyl)-ammoniumjodid der FormelFrom the Houben-Weyl (IV. Edition, 1958) vol. XI, 2, N-connections, Vol. II / III, page 606 it is known that the alkylation of N, N'-diphenyl-N, N'-diethylethylenediamine depending on Alkylating agent leads to different products. With Methyl iodide as the alkylation agent becomes the methylation of a tertiary amine nitrogen to N-methyl-N-ethyl-N-phenyl-N-  (N'-ethyl-N'-phenylaminoethyl) ammonium iodide of the formula

erreicht.reached.

Dimethylsulfat ergibt das bisquaternäre Ammoniumsalz der FormelDimethyl sulfate gives the bisquaternary ammonium salt formula

Erfindungsgemäß ist das N-Methyl-N-ethyl-N-phenyl-N-(N′ethyl- N′-phenylaminoethyl)-ammonium-methosulfat der Formel 7 zu er­ halten, wenn die Methylierung mit Dimethylsulfat in organischen Lösungsmitteln, wie z. B. Benzen oder Dimethylformamid erfolgt.According to the invention, the N-methyl-N-ethyl-N-phenyl-N- (N'ethyl- N'-phenylaminoethyl) ammonium methosulfate of formula 7 to he hold when the methylation with dimethyl sulfate in organic Solvents such as B. benzene or dimethylformamide.

Im Vergleich zu CI Basic Red 22, führen die erfindungsgemäßen Farbstoffe zu gleichmäßigeren Haarfärbungen.Compared to CI Basic Red 22, the inventive lead Dyes for more even hair coloring.

Gegenüber den bekannten kationischen DisazofarbstoffenCompared to the known cationic disazo dyes

die rotstichige Violettnuancen ergeben, werden mit den erfin­ dungsgemäßen Farbstoffen klare Rottöne erzielt.the reddish violet shades result with the inventions dyes according to the invention achieved clear shades of red.

Ausführungsbeispiel 1Embodiment 1

26,8 g N,N′-Diphenyl-N,N′-diethyl-ethylendiamin werden in 250 ml Benzen bei 80°C gelöst und 16,2 g Dimethylsulfat hin­ zugetropft und 4 h bei 80°C gerührt.26.8 g of N, N'-diphenyl-N, N'-diethyl-ethylenediamine are in 250 ml of benzene dissolved at 80 ° C and 16.2 g of dimethyl sulfate added dropwise and stirred at 80 ° C for 4 h.

Nach Abkühlen auf Raumtemperatur wird der ausgefallene Kristall­ brei vom Benzen abgetrennt und der Rückstand in 100 ml Wasser verrührt, und mit verdünnter Natronlauge auf pH6 gestellt, von einem geringen unlöslichen Rückstand wird abfiltriert. Die auf diese Weise erhaltene wäßrige Lösung enthält die Kupplungskom­ ponenteAfter cooling to room temperature, the precipitated crystal Porridge separated from the benzene and the residue in 100 ml of water stirred and adjusted to pH 6 with dilute sodium hydroxide solution, from a small insoluble residue is filtered off. The on the aqueous solution obtained in this way contains the coupling com component

Eine aus 8,4 g 3-Aminotriazol hergestellte salzsaure Diazo­ lösung wird unter gutem Rühren bei -2 bis -4°E zu der wäßrigen Lösung von 39,4 g der obigen Kupplungskomponente in ca. 30 min hinzugesetzt. Mit verdünnter Natronlauge wird auf pH5-6 gestellt. Die Kupplung ist danach beendet.A hydrochloric acid diazo made from 8.4 g of 3-aminotriazole Solution becomes the aqueous with good stirring at -2 to -4 ° E Solution of 39.4 g of the above coupling component in about 30 minutes added. The pH is adjusted to 5-5 with dilute sodium hydroxide solution. The clutch is then ended.

Nach Zugabe von 50 g Kochsalz wird 1 h nachgerührt und der Farb­ stoffAfter adding 50 g of sodium chloride, stirring is continued for 1 h and the color material

abgesaugt.aspirated.

λ max. (Methanol) 423,01 nm 41,3 g des obigen Kupplungsproduktes werden in 220 ml Wasser gelöst und mit 18 g ZnO verrührt. Bei 35-40°C werden 66 g Dimethylsulfat hinzugetropft und nach beendeter Zugabe weitere 2 h bei 35-40°C gerührt. λ max. (Methanol) 423.01 nm 41.3 g of the above coupling product are in 220 ml of water dissolved and stirred with 18 g ZnO. At 35-40 ° C, 66 g Dimethyl sulfate added dropwise and more after the addition Stirred at 35-40 ° C for 2 h.  

Nach beendeter Methylierung wird mit 100 ml Wasser versetzt und 1 h bei 60°C gerührt. Der Farbstoff wird mit 40 g Koch­ salz und 80 ml Zinkchloridlösung (17%ig) ausgefällt und abfil­ triert.After the methylation has ended, 100 ml of water are added and stirred at 60 ° C for 1 h. The dye is cooked with 40 g salt and 80 ml of zinc chloride solution (17%) precipitated and filtered trated.

Es werden 54 g des Farbstoffs der KonstitutionThere are 54 g of the dye of the constitution

λ max. (Methanol) 511,25 nm erhalten.λ max. (Methanol) 511.25 nm receive.

Ausführungsbeispiel 2Embodiment 2

Zu einer wäßrigen Lösung von 30,45 g N(N′-Ethyl-,N′-phenylamino­ ethyl)-N-phenyl-N,N-dimethyl-ammoniumchlorid (erhalten durch Um­ setzung von N-Ethyl-N-bromethylanilin mit Dimethylanilin) werden bei -2 bis -4°C die aus 8,4 g 3-Aminotriazol hergestellte Diazo­ lösung hinzugetropft.To an aqueous solution of 30.45 g of N (N'-ethyl, N'-phenylamino ethyl) -N-phenyl-N, N-dimethyl-ammonium chloride (obtained by Um setting of N-ethyl-N-bromethylaniline with dimethylaniline) at -2 to -4 ° C the diazo prepared from 8.4 g of 3-aminotriazole solution added dropwise.

Das Kupplungsgemisch wird mit verdünnter Natronlauge auf pH5-6 gestellt und nach beendeter Kupplung durch Zusatz von 50 g Koch­ salz und 1 stündigem Nachrühren der FarbstoffThe coupling mixture is adjusted to pH 5-6 with dilute sodium hydroxide solution provided and after coupling is completed by adding 50 g of cook salt and 1 hour stirring the dye

abgesaugt.aspirated.

λ max. (Methanol) 421,34 nm 40 g des obigen Kupplungsproduktes werden, wie in Beispiel 1 beschrieben, mit Dimethylsulfat in Wasser methyliert. λ max. (Methanol) 421.34 nm 40 g of the above coupling product are as in Example 1 described, methylated with dimethyl sulfate in water.  

Es werden 48 g des Farbstoffs der KonstitutionThere will be 48 g of the dye of the constitution

λ max. (Methanol) 510,21 nm erhalten.λ max. (Methanol) 510.21 nm receive.

Claims (1)

Kationische Azofarbstoffe zum Färben von Keratinmaterialien mit einem Farbstoffgehalt und für Keratinfärbemittel üblichen Zusätzen, gekennzeichnet durch den Gehalt an einem kationischen Monoazofarbstoff der allgemeinen Formel 1 worin R1 und R2 einen Methyl- und Ethylrest bedeuten, wobei R1 und R2 gleich oder verschieden sein kann.Cationic azo dyes for dyeing keratin materials with a dye content and additives customary for keratin dyes, characterized by the content of a cationic monoazo dye of the general formula 1 wherein R 1 and R 2 represent a methyl and ethyl radical, where R 1 and R 2 may be the same or different.
DE19924220388 1992-06-22 1992-06-22 Cationic azo dyes - for keratin materials showing improved evenness Withdrawn DE4220388A1 (en)

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US5879413A (en) * 1996-11-27 1999-03-09 Warner-Jenkinson Europe Limited Cationic diazo dyes for the dyeing of hair
FR2825703A1 (en) * 2001-06-11 2002-12-13 Oreal COMPOSITION FOR DYEING KERATINIC FIBERS COMPRISING A SPECIAL DICATION DIAZOIC DYE
US7172633B2 (en) 2003-06-16 2007-02-06 L'ORéAL S.A. Lightening dye composition comprising at least one cationic direct dye containing mixed chromophores
US7201779B2 (en) 2003-06-16 2007-04-10 L'oreal S.A. Dye composition comprising at least one direct dye containing mixed chromophores
US7300471B2 (en) 2004-02-27 2007-11-27 L'oreal S.A. Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes.
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US7488354B2 (en) 2004-10-14 2009-02-10 L'oreal S.A. Dyeing composition comprising at least one disulphide dye and method of dyeing human keratin fibers using this dye
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US7582122B2 (en) 2005-08-26 2009-09-01 L'oreal S.A. Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing
US8038731B2 (en) 2006-03-24 2011-10-18 L'oreal S.A. Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent disulphide dye
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FR2825703A1 (en) * 2001-06-11 2002-12-13 Oreal COMPOSITION FOR DYEING KERATINIC FIBERS COMPRISING A SPECIAL DICATION DIAZOIC DYE
WO2002100834A1 (en) * 2001-06-11 2002-12-19 L'oreal Dyeing composition for keratinous fibres comprising a particular dicationic diazo dye
US7001436B2 (en) 2001-06-11 2006-02-21 L'oreal S.A. Dyeing composition for keratinous fibres comprising a particular dicationic diazo dye
US7172633B2 (en) 2003-06-16 2007-02-06 L'ORéAL S.A. Lightening dye composition comprising at least one cationic direct dye containing mixed chromophores
US7201779B2 (en) 2003-06-16 2007-04-10 L'oreal S.A. Dye composition comprising at least one direct dye containing mixed chromophores
US7300471B2 (en) 2004-02-27 2007-11-27 L'oreal S.A. Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes.
US7488354B2 (en) 2004-10-14 2009-02-10 L'oreal S.A. Dyeing composition comprising at least one disulphide dye and method of dyeing human keratin fibers using this dye
US7582122B2 (en) 2005-08-26 2009-09-01 L'oreal S.A. Mixed cationic dyes comprising at least one anthraquinone chromophore and their use in methods of hair dyeing
US8038731B2 (en) 2006-03-24 2011-10-18 L'oreal S.A. Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent disulphide dye
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US8562693B2 (en) 2006-03-24 2013-10-22 L'oreal Method of dyeing and lightening keratin materials in the presence of a reducing agent comprising a fluorescent deisulphide dye
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