DE2109756A1 - Monoazo dyes - from diphenylamine coupling components for polyester fibres - Google Patents

Monoazo dyes - from diphenylamine coupling components for polyester fibres

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Publication number
DE2109756A1
DE2109756A1 DE19712109756 DE2109756A DE2109756A1 DE 2109756 A1 DE2109756 A1 DE 2109756A1 DE 19712109756 DE19712109756 DE 19712109756 DE 2109756 A DE2109756 A DE 2109756A DE 2109756 A1 DE2109756 A1 DE 2109756A1
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Prior art keywords
diphenylamine
methyl
hydrogen
acetylamino
cyano
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DE19712109756
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German (de)
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Hans Jürgen Dr 6700 Ludwigshafen Klipper Gerhard Dr 6800 Mannheim Quadbeck Seeger
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BASF SE
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Badische Anilin and Sodafabrik AG
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Priority to DE19712109756 priority Critical patent/DE2109756A1/en
Publication of DE2109756A1 publication Critical patent/DE2109756A1/en
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    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The dyes are of formula: (in which R is hydrogen, 1-4C alkyl, 2-3C hydroxyalkyl, beta-hydroxy gamma-chloro-proply, beta-chloroethyl, beta-acetoxyethyl, beta-acetoxypropyl or beta-propionyl oxyethyl. R1 is H or 1-4C alkyl, R2 is H, 2-9C carbalkoxy, cyano, carbonamido, opt. N-substd. with 1-8c alkyl gps. opt. substd. with hydroxy, 1-4C alkoxy or cyano. X is H, Cl, Br, OCH3, OC2H5, or CH3 and Y is H, Cl, OCH3, OC2H5, 2-9C carbalkoxy, opt. N-substd. carbonamido cyano or methyl). They are made by diazotising 2,4-dinitro- 6-cyano aniline and coupling with substd. diphenylamines. The dyes are suitable for dyeing and printing polyester fibres in violet to blue shades with good fastness to light and thermofixing.

Description

Neue Azofarbstoffe mit Diphenylaminkupplungskomponenten Die Erfindung betrifft Farbstoffe der allgemeinen Formel I in der R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Hydroxyalkyl mit 2 oder 9 C-Atomen, ß-Hydroxy- γ-chlorpropyl, ß-Chloräthvl, B-Acetoxyäthyl, ß-Acetoxypropyl oder ß-Propionyloxyäthyl, R1 Wasserstoff oder Alkyl mit 1 bis 4 C-Atomen, R2 Wasserstoff, Carbalkoxy mit insgesamt 2 bis 9 C-Atomen, Cyan,-Carbonamid, N-monosubstituiertes- oder N,N-disubstituiertes Carbonamid, wobei die gegebenenfalls durch Hydroxy, Alkoxy mit 1 bis 4 C-Atomen oder Oyan substituierten N-Substituenten Alkylreste mit 1 bis 8 C-Atomen sind, X Wasserstoff, Chlor, Brom, Methoxy, Äthoxy oder Methyl und Y Wasserstoff, Chlor, Methoxy, Äthoxy, Carbalkoxy mit 2 bis 9 C-Atomen, Carbonamid, N-mono- oder N,N-disubstituiertes Carbonamid, Cyan oder Methyl bedeuten.New azo dyes with diphenylamine coupling components The invention relates to dyes of the general formula I. in which R is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl with 2 or 9 carbon atoms, ß-hydroxy- γ-chloropropyl, ß-chloroethvl, B-acetoxyethyl, ß-acetoxypropyl or ß-propionyloxyethyl, R1 hydrogen or Alkyl with 1 to 4 carbon atoms, R2 hydrogen, carbalkoxy with a total of 2 to 9 carbon atoms, cyano, carbonamide, N-monosubstituted or N, N-disubstituted carbonamide, the optionally substituted by hydroxy, alkoxy with 1 to 4 C atoms or Oyan-substituted N substituents are alkyl radicals with 1 to 8 C atoms, X is hydrogen, chlorine, bromine, methoxy, ethoxy or methyl and Y is hydrogen, chlorine, methoxy, ethoxy, carbalkoxy with 2 to 9 C atoms, Mean carbonamide, N-mono- or N, N-disubstituted carbonamide, cyano or methyl.

Neben den schon genannten seien im einzelnen folgende Reste genannt: für R: Methyl, Äthyl, n- oder i-Propyl, n- oder i-Butyl, ß-Hydroxyäthyl, ß-Hydroxypropyl oder T -Hydroxypropyl.In addition to those already mentioned, the following residues should be mentioned in detail: for R: methyl, ethyl, n- or i-propyl, n- or i-butyl, ß-hydroxyethyl, ß-hydroxypropyl or T -hydroxypropyl.

für R1: Methyl, Äthyl, n- oder i-Propyl, n- oder i-Butyl.for R1: methyl, ethyl, n- or i-propyl, n- or i-butyl.

für R2: Carbomethoxy-,-äthoxy, -propoxy, -butoxy, -hexoxy, -ß-äthylhexoxy, Carbonamid, N-Methyl-carbonamid, N-Äthyl-, N-Propyl-, N-Butyl-, ß-Äthyl-hexyl-, N-ß-Hydroxyäthyl-, N-ß-Hydroxypropyl-, N-ß-Cyanäthyl-, N-ß-Methoxyäthyl-, N-γ-Methoxypropyl-, N,N-Dimethylcarbonamid, N,N-Diäthyl-, N,N-Dibutyl-, N-Methyl-N-ß-hydroxyäthyl-, N-Äthyl-N-ß-hydroxyäthyl- oder N-Butyl-N-ß-hydroxyäthyl-carbonamid.for R2: carbomethoxy -, - ethoxy, -propoxy, -butoxy, -hexoxy, -ß-ethylhexoxy, Carbonamide, N-methyl-carbonamide, N-ethyl-, N-propyl-, N-butyl-, ß-ethyl-hexyl-, N-ß-hydroxyethyl, N-ß-hydroxypropyl, N-ß-cyanoethyl, N-ß-methoxyethyl, N-γ-methoxypropyl-, N, N-dimethylcarbonamide, N, N-diethyl-, N, N-dibutyl-, N-methyl-N-ß-hydroxyethyl-, N-ethyl-N-ß-hydroxyethyl or N-butyl-N-ß-hydroxyethyl carbonamide.

für Y: Carbomethoxy, -äthoxy, -propoxy, -butoxy, -hexoxy oder äthylhexoxy sowie die für R2 genannten Oarbonamidreste.for Y: carbomethoxy, -ethoxy, -propoxy, -butoxy, -hexoxy or ethylhexoxy as well as the carbonamide residues mentioned for R2.

Die neuen Farbstoffe sind violett bis blau und eignen sich insbesondere zum Färben von synthetischen Polyestern wie Polyäthylenglykol-terephthalat oder chemisch analog aufgebauten Polymeren. Man erhält farbstarke Färbungen mit vorzüglichen Echtheiten, besonders sehr guter Licht- und Thermofixierechtheit.The new dyes are purple to blue and are particularly suitable for dyeing synthetic polyesters such as polyethylene glycol terephthalate or chemically analogous polymers. Strong dyeings with excellent color are obtained Fastness properties, especially very good fastness to light and heat-setting.

Anstelle von einheitlichen Farbstoffen kann beim Färben die Verwendung von Farbstoffgemischen vorteilhaft sein, die man durch mechanisches Mischen oder vorzugsweise durch den Gebrauch von mehr als einer Eupplungskomponente bei der Herstellung der Farbstoffe erhält.Instead of uniform dyes when dyeing can use of dye mixtures that can be obtained by mechanical mixing or preferably through the use of more than one coupling component in manufacture which receives dyes.

Von besonderer technischer Bedeutung sind Farbstoffe der Formel Ia in der R3 Methyl oder Äthyl, R4 Wasserstoff, Methyl, Äthyl, ß-Hydroxyäthyl, ß-Hydroxypropyl, ß-Chloräthyl, ß-Acetoxyäthyl oder B-Acetoxypropyl, X1 Wasserstoff, Chlor, Methoxy, Äthoxy oder Methyl und Y1 Wasserstoff, Chlor, Methoxy, Äthoxy oder Methyl bedeuten.Dyes of the formula Ia are of particular industrial importance in which R3 is methyl or ethyl, R4 is hydrogen, methyl, ethyl, ß-hydroxyethyl, ß-hydroxypropyl, ß-chloroethyl, ß-acetoxyethyl or B-acetoxypropyl, X1 is hydrogen, chlorine, methoxy, ethoxy or methyl and Y1 is hydrogen, chlorine, Mean methoxy, ethoxy or methyl.

Von den Verbindungen der Formel Ia sind insbesondere Farbstoffe mit R3 = H3 und R4 = H bevorzugt.Of the compounds of the formula Ia, there are in particular dyes with R3 = H3 and R4 = H preferred.

Zur Herstellung der neuen Farbstoffe der Formel I kann man die nach üblichen Methoden hergestellte Diazoverbindung des 2.4-Dinitro-6-cyan-anilins mit Diphenylaminen der Formel III umsetzen.To prepare the new dyes of the formula I, the diazo compound of 2,4-dinitro-6-cyano-aniline, prepared by customary methods, can be used with diphenylamines of the formula III realize.

Verbindungen der Formel III sind beispielsweise: 3-Pormylamino-diphenylamin, 3-Acetylamino-diphenylamin, 3-Propionylamino-diphenylamin, 3-Acetylamino-N-methyl diphenylamin, 3-Acetylamino-N-äthyl-diphenylamin, 3-Acetylamino-N-ß-hydroxyäthyl-diphenylamin, 3-Acetylamino-N-ßhydroxypropyl-diphenylamin, 3-Acetylamino-N-ß-acetoxy-diphenylamin, 3-Acetylamino-N-ß-acetoxypropyl-diphenylamin, 3-Propionylamino-N-methyl-diphenylamin, 3-Propionylamino-N-äthyl-diphenylamin, 3-Propionylamino-N-ß-hydroxyäthyldiphenylamin, 3-Propionyl-amino-N-ß-hydroxypropyl-diphenylamin, 3-Acetylamino-4'-chlor-diphenylamin, 3-Acetylamino-4'-methyl-diphenylamin, 3-Acetylamino-2'-äthoxy-diphenylamin, 3-Acetylamino-2'-methoxy-diphenylamin, 3-Acetylamino-2'-methyl-diphenyl-amin, 3-Acetylamino-2'-chlor-diphenylamin, 3-Acetylamino-2',4'-dimethyl-diphenylamin, 3-Acetylamino-2'-4' -dimethoxy-diphenylamin, 3-Acetylamino-2'-carbomethoxydiphenylamin, 3-Acetylamino-2'-carboäthoxy-diphenylamin, 3-Acetylamino-2'-carbo-butoxy-diphenylamin, 3-Propionylamino-4'-chlor-diphenylamin, 3-Propionylamino-4'-methyldiphenylamin, 3-Propionylamino-2'-äthoxy-diphenylamin, 3-Propionylamino-2'-methoxy-diphenylamin, 3-Acetylamino-N-ßhydroxyäthyl-4'-methyl-diphenylamin, 3-Acetylamino-N-methyl-4'-chlor-diphenylamin, 3-Acetylamino-N-ß-hydroxypropyl-4'-methyl-diphenylamin, 3-Acetylamino-N-ß-hydroxyäthyl-4'-methyl-diphenylamin, 3-Propionylamino-N-ß-hydroxyäthyl-4'-methyl-diphenylamin, 3-Propionylamino-N-ß-hydroxyäthyl-4' -chlor-diphenylamin, 3-Propionylamino-N-ß-hydroxyäthyl-2'-methoxydiphenylamin, 3-Acetylamino-6-cyandiphenylamin, 3-Propionylamino-6-cyan-diphenylamin, 3-Acetylamino-6-cyan- 2'-äthoxy-diphenylamin, 3-Acetylamlno-6-cyan-4'-methyl-diphenylamin, 3-Acetylamino-6-cyan-2'-methoxy-diphenylamin, 3-Acetylamino-6-carbonamido-diphenylamin, 3-Propionylamino-6-carbonamido-diphenylamin, 3-Acetylamino-6-(N-methylcarbonamido)-diphenylmin, 3-Acetylamino-6-(N,N-dimethylcarbonamido)-diphenylamin, 3-Acetylamino-6-(N-n-butyl-carbonamido )-diphenylamin, 3-Acetylamino-6-(N-ß-hydroxyäthyl-carbonamido)-diphenylamin, 3-Acetylamino-6-carbonamido-4' -methyl-diphenylamin, 3-Acetvlamino-6-carbonamido-4' -chlor-diphenylamin, 3-Acetylamino-6-(N,N-dimethyl-carbonamido)-4'-methyl-diphenylamin, 3-Acetylamino-6-carbomethoxy-diphenylamin, 3-Propionylamino-6-carboäthoxy-diphenylamin, 3-Acetylamino-6-carbobutoxydiphenylamin, 3-Acetylamino-6-carbohexoxy-diphenylamin, 3-Acetylamino-6-carbomethoxy-4'-methyl-diphenylamin oder 3-Acetylamino-6-carboäthoxy-4 -chlor-diphenylamin' 3-Acetylamino-2'-carbonamido-diphenylamin, 3-Propionylamino-2'-(N-methylcarbonamido)-diphenylamin, 3-Acetylamino-2'-(N,N-dimethylcarbon-amido)-diphenylamin, 3-Acetylamino-2'-cyandiphenylamin, 3-Acetylamino-2' . 6-dicyan-diphenylamin, 3-Acetylamino-N-ß-chloräthyl-diphenylamin.Compounds of the formula III are for example: 3-pormylamino-diphenylamine, 3-acetylamino-diphenylamine, 3-propionylamino-diphenylamine, 3-acetylamino-N-methyl diphenylamine, 3-acetylamino-N-ethyl-diphenylamine, 3-acetylamino-N-ß-hydroxyethyl-diphenylamine, 3-acetylamino-N-ß-hydroxypropyl-diphenylamine, 3-acetylamino-N-ß-acetoxy-diphenylamine, 3-acetylamino-N-ß-acetoxypropyl-diphenylamine, 3-propionylamino-N-methyl-diphenylamine, 3-propionylamino-N-ethyl-diphenylamine, 3-propionylamino-N-ß-hydroxyethyldiphenylamine, 3-propionyl-amino-N-ß-hydroxypropyl-diphenylamine, 3-acetylamino-4'-chloro-diphenylamine, 3-acetylamino-4'-methyl-diphenylamine, 3-acetylamino-2'-ethoxy-diphenylamine, 3-acetylamino-2'-methoxy-diphenylamine, 3-acetylamino-2'-methyl-diphenyl-amine, 3-acetylamino-2'-chloro-diphenylamine, 3-acetylamino-2 ', 4'-dimethyl-diphenylamine, 3-acetylamino-2'-4'-dimethoxy-diphenylamine, 3-acetylamino-2'-carbomethoxydiphenylamine, 3-acetylamino-2'-carboethoxy-diphenylamine, 3-acetylamino-2'-carbo-butoxy-diphenylamine, 3-propionylamino-4'-chloro-diphenylamine, 3-propionylamino-4'-methyldiphenylamine, 3-propionylamino-2'-ethoxy-diphenylamine, 3-propionylamino-2'-methoxy-diphenylamine, 3-acetylamino-N-ß-hydroxyethyl-4'-methyl-diphenylamine, 3-acetylamino-N-methyl-4'-chloro-diphenylamine, 3-acetylamino-N-ß-hydroxypropyl-4'-methyl-diphenylamine, 3-acetylamino-N-ß-hydroxyethyl-4'-methyl-diphenylamine, 3-propionylamino-N-ß-hydroxyethyl-4'-methyl-diphenylamine, 3-propionylamino-N-ß-hydroxyethyl-4 ' -chlor-diphenylamine, 3-propionylamino-N-ß-hydroxyethyl-2'-methoxydiphenylamine, 3-acetylamino-6-cyandiphenylamine, 3-propionylamino-6-cyano-diphenylamine, 3-acetylamino-6-cyano- 2'-ethoxy-diphenylamine, 3-acetylamino-6-cyano-4'-methyl-diphenylamine, 3-acetylamino-6-cyano-2'-methoxy-diphenylamine, 3-acetylamino-6-carbonamido-diphenylamine, 3-propionylamino-6-carbonamido-diphenylamine, 3-acetylamino-6- (N-methylcarbonamido) -diphenylmin, 3-acetylamino-6- (N, N-dimethylcarbonamido) -diphenylamine, 3-acetylamino-6- (N-n-butyl-carbonamido) -diphenylamine, 3-acetylamino-6- (N-ß-hydroxyethyl-carbonamido) -diphenylamine, 3-acetylamino-6-carbonamido-4 '-methyl-diphenylamine, 3-acetylamino-6-carbonamido-4' -chlor-diphenylamine, 3-acetylamino-6- (N, N-dimethyl-carbonamido) -4'-methyl-diphenylamine, 3-acetylamino-6-carbomethoxy-diphenylamine, 3-propionylamino-6-carboethoxy-diphenylamine, 3-acetylamino-6-carbobutoxydiphenylamine, 3-acetylamino-6-carbohexoxy-diphenylamine, 3-acetylamino-6-carbomethoxy-4'-methyl-diphenylamine or 3-acetylamino-6-carboethoxy-4 -chlor-diphenylamine '3-acetylamino-2'-carbonamido-diphenylamine, 3-propionylamino-2' - (N-methylcarbonamido) -diphenylamine, 3-acetylamino-2 '- (N, N-dimethylcarbon-amido) -diphenylamine, 3-acetylamino-2'-cyandiphenylamine, 3-acetylamino-2 '. 6-dicyanodiphenylamine, 3-acetylamino-N-ß-chloroethyl-diphenylamine.

Im folgenden beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following, information on parts and percentages relate to the extent that not otherwise noted, on weight.

Beispiel 1 5,2 Teile (0,025 Mol) 2,4-Dinitro-6-cyan-anilin werden in 33 Volumteilen konzentrierter Schwefelsäure gelöst und bei 0 bis 5 °0 langsam mit 25 Volumteilen Eisessig/Propionsäure (17 : 3) versetzt. Dann werden bei 0 bis 5 °a langsam 7,5 Teile Nitrosylschwefelsäure zugefügt und min rührt 3 Stunden bei dieser Temperatur. Die Diazolö,ung gibt man dann bei 0 bis 5 °O allmählich zur Lösung von 6,0 Teilen (0,025 Mol) 3-Acetylamino-4'-methyl-diphenylamin in 40 Volumteilen Methanol, 40 Teilen Wasser und ungefähr 0,5 Teilen Amidosulfonsäure. Nach beendeter Kupplung wird der Farbstoff abgesaugt und mit Wasser neutral gewaschen. Nach dem Trocknen bei 60 0 unter vermindertem Druck erhält man 8,0 Teile des Farbstoffs der Formel der Polyester in blauen Farbtönen mit sehr guter Licht- und Thermofixierechtheit färbt.Example 1 5.2 parts (0.025 mol) of 2,4-dinitro-6-cyano-aniline are dissolved in 33 parts by volume of concentrated sulfuric acid and 25 parts by volume of glacial acetic acid / propionic acid (17: 3) are slowly added at 0 to 5 °. 7.5 parts of nitrosylsulfuric acid are then slowly added at 0 ° to 5 ° C. and the mixture is stirred for 3 hours at this temperature. The diazole solution is then gradually added at 0 ° to 5 ° C. to a solution of 6.0 parts (0.025 mol) of 3-acetylamino-4'-methyl-diphenylamine in 40 parts by volume of methanol, 40 parts of water and about 0.5 part of sulfamic acid . After the coupling has ended, the dye is filtered off with suction and washed neutral with water. After drying at 60 ° under reduced pressure, 8.0 parts of the dye of the formula are obtained the polyester dyes in blue shades with very good fastness to light and thermosetting.

Beispiel 2 5,2 Teile 2.4-Dinitro-6-cyano-anilin werden wie in Beispiel 1 diazotiert und mit der Lösung von 5,6 Teilen 3-Acetylaminodiphenylamin in 40 Volumteilen Methanol, 40 Teilen Wasser und ungefähr 0,5 Teilen Amidosulfonsäure vereinigt. Der ausgefallene Farbstoff wird abgesaugt und mit Wasser neutral gewaschen. Nach dem Trocknen bei 60 °C unter vermindertem Druck erhält man 10,6 Teile des Farbstoffs der Formel der Polyester in blauen Tönen mit sehr guten Echtheiten färbt.Example 2 5.2 parts of 2,4-dinitro-6-cyano-aniline are diazotized as in Example 1 and combined with the solution of 5.6 parts of 3-acetylaminodiphenylamine in 40 parts by volume of methanol, 40 parts of water and approximately 0.5 part of sulfamic acid. The precipitated dye is filtered off with suction and washed neutral with water. After drying at 60 ° C. under reduced pressure, 10.6 parts of the dye of the formula are obtained the polyester dyes in blue tones with very good fastness properties.

Beispiel 3 5,2 Teile 2.4-Dinitro-6-cyano-anilin werden wie in Beispiel 1 diazotiert und mit der Lösung von 9,1 Teilen 3-Acetylamino-4'-chlor-diphenvlamin in 40 Teilen Methanol, 40 Teilen Wasser und Amidosulfonsäure vereinigt. Man erhält nach Trocknen bei 60 °O unter vermindertem Druck 9,5 Teile des Farbstoffs der Formel der Polyester in blauen Tönen mit sehr guten Echtheiten färbt.Example 3 5.2 parts of 2,4-dinitro-6-cyano-aniline are diazotized as in Example 1 and mixed with the solution of 9.1 parts of 3-acetylamino-4'-chlorodiphenylamine in 40 parts of methanol, 40 parts of water and sulfamic acid united. After drying at 60.degree. C. under reduced pressure, 9.5 parts of the dyestuff of the formula are obtained the polyester dyes in blue tones with very good fastness properties.

Beispiel 4 5,2 Teile 2,4-Dinitro-6-cyano-anilin werden wie in Beispiel 1 diazotiert und mit der Lösung von 6,0 Teilen 3-Acetylamino-N-methyl-diphenylamin in 40 Volumteilen Methanol, 40 Teilen Wasser und Amidosulfonsäure vereinigt. Der ausgefallene Farbstoff wird abgesaugt und mit Wasser neutral gewaschen. Nach Trocknen bei 60 °C unter vermindertem Druck erhält man 8,5 Teile des Farbstoffs der Formel der Polyester in blauen Tönen mit sehr guten Echtheiten färbt.Example 4 5.2 parts of 2,4-dinitro-6-cyano-aniline are diazotized as in Example 1 and with the solution of 6.0 parts of 3-acetylamino-N-methyl-diphenylamine in 40 parts by volume of methanol, 40 parts of water and Amidosulfonic acid combined. The precipitated dye is filtered off with suction and washed neutral with water. After drying at 60 ° C. under reduced pressure, 8.5 parts of the dye of the formula are obtained the polyester dyes in blue tones with very good fastness properties.

Beispiel 5 5,2 Teile 2,4-Dinitro-6-cyano-anilin werden wie in Beispiel 1 diazotiert und mit 8,7 Teilen 3-Acetylamino-N-ß-acetoxyäthyl 4'-chlordiphenylamin gekuppelt, die in 40 Volumteilen Methanol, 40 Teilen Wasser und Amidosulfonsäure gelöst sind. Man erhält nach Trocknen bei 60 OC unter vermindertem Druck 12,5 Teile des Farbstoffs der Formel der Polye3ter in blauen Tönen mit sehr guten Echtheiten färbt.Example 5 5.2 parts of 2,4-dinitro-6-cyano-aniline are diazotized as in Example 1 and coupled with 8.7 parts of 3-acetylamino-N-ß-acetoxyethyl 4'-chlorodiphenylamine, which is dissolved in 40 parts by volume of methanol, 40 parts of water and sulfamic acid are dissolved. After drying at 60 ° C. under reduced pressure, 12.5 parts of the dyestuff of the formula are obtained the polyether dyes in blue tones with very good fastness properties.

Analog der beschriebenen Arbeitsweise erhält man die in der folgenden Tabelle durch Angabe der Substituenten charakterisierten Farbstoffe: Farbton auf Beisp. Ri R2 X Y R Polyester 6 H H H H H blau 7 CH3 H H H H 02H5 blau 8 CH3 H H H H 50 % blau C2H40H 50 % 9 OH3 H K H H 60 % blau 3 CH2-CH-CH3 40 % 209838/1146 OH Farbton auf Beisp. R1 R2 X . Y R Polyester 10 CH3 H H H H 60 % blau CH2-CH-OH 40 % CH2Cl 11 CH3 H 11 2'-CONH2 H blauviolett 0 12 0113 H H H H 11 50 % blau 3 C2H4-OC-CH3 50% 13 CH3 H 11 4'O113 CH3 blau 14 OH3 H 2'-CH3 4'-CH3 H blau 15 CH3 H 11 2'-CON(CH3)2 H blauviolett 16 OH3 H K 4'-CH H 60 blau CH2-CH-OH 40 % CH2 C1 2 17 OH3 H 2'-OCH H H blauen 18 GE H 2'-OCHg H H 50 % blaugrün 3 3 CH2-CH2-OH 50 % 19 CH3 H 2'-Cl H K blau 20 CH3 11 H 4'-CH3 CH2-CH2-OH blau 21 OH3 3 H 4'-CH3 H 60 % blau CH2CH20-C-CH3 0 40 % 22 O2H5 H H 2'-CONHCH3 CH2-CH2-OH 40 % blauviolett H 60 % 23 CH3 H H 4'-Cl H 60 % blau CH2CH2-OH 40 ffi 24 CH3 H 2'-CH3 4'-CH3 H 50 ffi blau CH2CH2-OH 50 % 25 CH H H 4'-CH3 H 40 ffi blau 3 CH2-CH-OH 60 % CH3 26 CH3 3 2'00H3 5 H3 H blauen 27 02115 H H H H blau Farbton auf Beisp. R1 R2 X Y R Polyester 28 C2H5 H H H CH3 blau 29 C2H5 H H 4'-CH3 H blau 30 C2H5 H 2'-CH3 4'-CH3 H blau 31 C2H5 H H 4'-Cl H blau 32 C2H5 H H H H 40% blau 2 5 C2H4OH 60% 33 C2H5 H H 2'-OC2H5 H blaugrün 34 C2H5 H 2'-Cl 4'-Cl H blau 35 C3H7 H H H H blau 36 C3H7 H H 4'-CH3 H blau 37 C4H9 H H H H blau 38 CH3 COOC2H5 H H H blauviolett 39 CH3 COOCH3 H 4'-CH3 H " 40 CH3 COOCH3 H 4'-Cl H " 41 CH3 COOCH3 H 4'-OCH3 H 42 CH3 COOC3H7 H H H ?1 43 CH3 COOC4H9 H. H H 1I 44 CH3 COOC6H13 H H H " 45 C2H5 COOCH3 H 4'-CH3 H n 46 CH3 CN H H H " 47 CH3 CONH2 H H H " 48 CH3 CONHCH3 H H H " 49 CH3 CON(CH3)2 H H H " 50 CH3 CONHC4H9 H H H " 51 CH3 CONHC2H4-OH H H H " 52 CH3 " H 4'-CH3 H " 53 CH3 " H 4'-Cl H " Farbton auf Beisp. R1 R2 X Y R Polyester 54 0113 CON(C4Hg)2 H 4'-CH3 H blauviolett 55 02115 CONHC3H7 H H H blauviolett 56 CH3 CO(0H3)2 H 4e-CH3 H n11 57 CH CON/ 3 H H 11 NO 2114011 OH 58 3 XCzH40H H 5 11 4'-CH3 H » O2H4011 59 CH3 COSH(CH2)3-OCH3 H H H 60 0113 COWH(CH2)3-OCH3 11 4'-CH3 H n 61 CX3 CORH-C2H4-CK H H H 11 62 CE3 H H 2'-COOCH3 H 63 02115 H H 2'-C00a2Hg 11 64 CH3 11 H 2'-COOC3H7 H 65 3 H 11 2'-COOC4Hg H 66 02115 H H 2'-COOC6H13 H 67 02115 H H 2'-CN H 68 CH3 CN H 2'-ON H » iCH, H It 69 02115 H B 2'-CON 21-O0N L rt 70 CH3 COOCH3 H 2'-COOCH3 H t11 71 CH3 H H 2'-CON(C4Hgu H The dyes characterized in the following table by specifying the substituents are obtained analogously to the procedure described: Color based on example Ri R2 XYR polyester 6 HHHHH blue 7 CH3 HHHH 02H5 blue 8 CH3 HHHH 50% blue C2H40H 50% 9 OH3 HKHH 60% blue 3 CH2-CH-CH3 40% 209838/1146 OH Color on example R1 R2 X. YR polyester 10 CH3 HHHH 60% blue CH2-CH-OH 40% CH2Cl 11 CH3 H 11 2'-CONH2 H blue-violet 0 12 0113 HHHH 11 50% blue 3 C2H4-OC-CH3 50% 13 CH3 H 11 4'O113 CH3 blue 14 OH3 H 2'-CH3 4'-CH3 H blue 15 CH3 H 11 2'-CON (CH3) 2 H blue-violet 16 OH3 HK 4'-CH H 60 blue CH2-CH-OH 40% CH2 C1 2 17 OH3 H 2'-OCH HH blue 18 GE H 2'-OCHg HH 50% blue-green 3 3 CH2-CH2-OH 50% 19 CH3 H 2'-Cl HK blue 20 CH3 11 H 4'-CH3 CH2-CH2-OH blue 21 OH3 3 H 4'-CH3 H 60% blue CH2CH20-C-CH3 0 40% 22 O2H5 HH 2'-CONHCH3 CH2-CH2-OH 40% blue-violet H 60% 23 CH3 HH 4'-Cl H 60% blue CH2CH2-OH 40 ffi 24 CH3 H 2'-CH3 4'-CH3 H 50 ffi blue CH2CH2-OH 50% 25 CH HH 4'-CH3 H 40 ffi blue 3 CH2-CH-OH 60% CH3 26 CH3 3 2'00H3 5 H3 H blue 27 02115 HHHH blue Color on example R1 R2 XYR polyester 28 C2H5 HHH CH3 blue 29 C2H5 HH 4'-CH3 H blue 30 C2H5 H 2'-CH3 4'-CH3 H blue 31 C2H5 HH 4'-Cl H blue 32 C2H5 HHHH 40% blue 2 5 C2H4OH 60% 33 C2H5 HH 2'-OC2H5 H blue-green 34 C2H5 H 2'-Cl 4'-Cl H blue 35 C3H7 HHHH blue 36 C3H7 HH 4'-CH3 H blue 37 C4H9 HH HH blue 38 CH3 COOC2H5 HHH blue-violet 39 CH3 COOCH3 H 4'-CH3 H "40 CH3 COOCH3 H 4'-Cl H" 41 CH3 COOCH3 H 4'-OCH3 H 42 CH3 COOC3H7 HHH? 1 43 CH3 COOC4H9 H. HH 1I 44 CH3 COOC6H13 HHH "45 C2H5 COOCH3 H 4'-CH3 H n 46 CH3 CN HHH "47 CH3 CONH2 HHH" 48 CH3 CONHCH3 HHH "49 CH3 CON (CH3) 2 HHH" 50 CH3 CONHC4H9 HHH "51 CH3 CONHC2H4-OH HHH" 52 CH3 "H 4'- CH3 H "53 CH3" H 4'-Cl H "shade on ex. R1 R2 XYR polyester 54 0113 CON (C4Hg) 2 H 4'-CH3 H blue-violet 55 02115 CONHC3H7 HHH blue-violet 56 CH3 CO (OH3) 2 H 4e-CH3 H n11 57 CH CON / 3 HH 11 NO 2114011 OH 58 3 XCzH40H H 5 11 4'-CH3 H » O2H4011 59 CH3 COSH (CH2) 3-OCH3 HHH 60 0113 COWH (CH2) 3-OCH3 11 4'-CH3 H n 61 CX3 CORH-C2H4-CK HHH 11 62 CE3 HH 2'-COOCH3 H 63 02115 HH 2'-C00a2Hg 11 64 CH3 11 H 2'-COOC3H7 H 65 3 H 11 2'-COOC4Hg H. 66 02115 HH 2'-COOC6H13 H 67 02115 HH 2'-CN H 68 CH3 CN H 2'-ON H » I, H It 69 02115 HB 2'-CON 21-O0N L rt 70 CH3 COOCH3 H 2'-COOCH3 H t11 71 CH3 HH 2'-CON (C4Hgu H.

Claims (5)

Patentansprüche 1. Neue Azofarbstoffe mit Diphenylaminkupplungskomponenten der allgemeinen Formel in der.Claims 1. New azo dyes with diphenylamine coupling components of the general formula in the. R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen,Hydroxyalkyl mit 2 oder 3 C-Atomen, ß-Hydroxy-γ-chlorpropyl, ß-Chloräthyl, ß-Acetoxyäthyl, ß-Acetoxypropyl oder ß-Propionyloxyäthyl, R1 Wasserstoff oder Alkyl mit 1 bis 4 C-Atomen, R2 Wasserstoff, Carbalkoxy mit insgesamt 2 bis 9 C-Atomen, Cyan, Carbonamid, N-monosubsttuiertes- oder N,N-disubstituiertes Carbonamid, wobei die gegebenenfalls durch Hydroxy, Alkoxy mit 1 bis 4 C-Atomen oder Cyan substituierten N-Substituenten Alkylreste mit 1 bis 8 C-Atomen sind, X Wasserstoff, Chlor, Brom, Methoxy, Äthoxy oder Methyl und Y Wasserstoff, Chlor, Methoxy, Äthoxy, Carbalkoxy mit 2 bis 9 C-Atomen, Carbonamid, N-mono- oder N,N-disubstituiertes Carbonamid, Cyan oder Methyl bedeuten. R is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl with 2 or 3 carbon atoms, ß-hydroxy-γ-chloropropyl, ß-chloroethyl, ß-acetoxyethyl, ß-acetoxypropyl or ß-propionyloxyethyl, R1 is hydrogen or alkyl with 1 to 4 carbon atoms, R2 is hydrogen, Carbalkoxy with a total of 2 to 9 carbon atoms, cyano, carbonamide, N-monosubstituted- or N, N-disubstituted carbonamide, the optionally substituted by hydroxy, alkoxy with 1 to 4 carbon atoms or cyano-substituted N-substituents alkyl radicals with 1 to 8 carbon atoms are, X is hydrogen, chlorine, bromine, methoxy, ethoxy or methyl and Y is hydrogen, Chlorine, methoxy, ethoxy, carbalkoxy with 2 to 9 carbon atoms, carbonamide, N-mono- or Mean N, N-disubstituted carbonamide, cyano or methyl. 2. Farbstoffe gemäß Anspruch 1 der allgemeinen Formel in der R3 Methyl oder Äthyl, R4 Wasserstoff, Methyl, Äthyl, ß-Hydroxyäthyl, ß-Hydroxypropyl, ß-Chloräthvl, ß-Acetoxyäthyl oder B-Acetoxypropyl, X1 Wasserstoff, Chlor, Methoxy, Äthoxy oder Methvl und y1 Wasserstoff, Chlor, Methoxy, Äthoxy oder Methyl bedeuten.2. Dyestuffs according to Claim 1 of the general formula in which R3 is methyl or ethyl, R4 is hydrogen, methyl, ethyl, ß-hydroxyethyl, ß-hydroxypropyl, ß-chloroethylene, ß-acetoxyethyl or B-acetoxypropyl, X1 is hydrogen, chlorine, methoxy, ethoxy or methyl and y1 is hydrogen, chlorine, Mean methoxy, ethoxy or methyl. 3. Die Verwendung der Farbstoffe gemäß Anspruch 1 oder 2 zum Färben von Textilmaterial aus Polvestern.3. The use of the dyes according to claim 1 or 2 for dyeing of textile material from Pole Eve. 4. Die Verwendung von Farbstoffgemischen gemäß Anspruch 3.4. The use of dye mixtures according to claim 3. 5. Ein Verfahren zur Herstellung von Farbstoffen gemäß Anspruch 1, dadurch gekennzeichnet, daß man eine Diazoverbindung des 2,4-Dinitro-6-cyananilins mit Diphenylaminen der allgemeinen Formel kuppelt.5. A process for the preparation of dyes according to claim 1, characterized in that a diazo compound of 2,4-dinitro-6-cyananiline with diphenylamines of the general formula clutch.
DE19712109756 1971-03-02 1971-03-02 Monoazo dyes - from diphenylamine coupling components for polyester fibres Pending DE2109756A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2193062A1 (en) * 1972-07-13 1974-02-15 Bayer Ag
US5270456A (en) * 1990-07-10 1993-12-14 Basf Aktiengesellschaft Azo dyes with A2-aminothiophene dye azo component and a coupling component and coupling component of the diphenylamine series

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2193062A1 (en) * 1972-07-13 1974-02-15 Bayer Ag
US5270456A (en) * 1990-07-10 1993-12-14 Basf Aktiengesellschaft Azo dyes with A2-aminothiophene dye azo component and a coupling component and coupling component of the diphenylamine series

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