DE3517365A1

DE3517365A1 - Dyes containing thiophene radicals

Info

Publication number: DE3517365A1
Application number: DE19853517365
Authority: DE
Inventors: Karl-Heinz Dr. 6710 Frankenthal Etzbach; Günter Dr. Hansen; Helmut Dr. 6701 Niederkirchen Reichelt; Ernst Dr. 6700 Ludwigshafen Schefczik
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 1985-05-14
Filing date: 1985-05-14
Publication date: 1986-11-27
Also published as: DD259201A5; ZA863524B; JPS61266466A

Abstract

The invention relates to compounds of the general formula I <IMAGE> in which X is fluorine, chlorine, bromine or optionally substituted hydroxyl or mercapto, Y is cyano, nitro, alkanoyl, aroyl, alkylsulphonyl, arylsulphonyl, carboxyl, carboxylic ester or optionally substituted carbamoyl, T is hydrogen, C1- to C4-alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula -CH=T<1>, where T<1> is the radical of a methylene-active compound, and K is the radical of a coupling component. The compounds according to the invention are preferably suitable for the dyeing of textile material composed of synthetic polyesters.

Description

Farbstoffe mit ThiophenrestenDyes with thiophene residues

Die Erfindung betrifft Verbindungen der allgemeinen Formel I in der X Fluor, Chlor, Brom oder gegebenenfalls substituiertes Hydroxy oder Mercapto, Y Cyan, Nitro, Alkanoyl, Aroyl, Alkylsulfonyl, Arylsulfonyl, Carboxyl, Carbonester oder gegebenenfalls substituiertes Carbamoyl, T Wasserstoff, C1- bis C4-Alkyl, ein durch elektrophile Substitution einführbarer Rest oder ein Rest der Formel -CH=T1, wobei T1 der Rest einer methylenaktiven Verbindung ist,und K der Rest einer Kupplungskomponente sind.The invention relates to compounds of the general formula I. in which X is fluorine, chlorine, bromine or optionally substituted hydroxy or mercapto, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, carbon ester or optionally substituted carbamoyl, T is hydrogen, C1- to C4-alkyl, by electrophilic substitution introducable radical or a radical of the formula -CH = T1, where T1 is the radical of a methylene-active compound and K is the radical of a coupling component.

Reste X sind neben den bereits genannten z. B. Alkoxy-, Cycloalkoxy, Aralkyloxy- oder Aroxygruppen sowie die entsprechenden Mercaptoreste. Im einzelnen seien beispielsweise OH, OCH3, OC2Hs, OC3H7, OC4Hg, OCH2C6H5.X radicals are in addition to the z. B. alkoxy, cycloalkoxy, Aralkyloxy or aroxy groups and the corresponding mercapto radicals. In detail are for example OH, OCH3, OC2Hs, OC3H7, OC4Hg, OCH2C6H5.

OC6H11, OC6H5, OC6H4CH3, OC6H4C1, SH, SCH3, SC2H5, SC3H7, S4Hg, SCH2C6H5.OC6H11, OC6H5, OC6H4CH3, OC6H4C1, SH, SCH3, SC2H5, SC3H7, S4Hg, SCH2C6H5.

SC2H40H, SCH2COOCH3, SCH2COOC2H5, SC6H11, SC6H5 oder SC6H4CH3 genannt.Called SC2H40H, SCH2COOCH3, SCH2COOC2H5, SC6H11, SC6H5 or SC6H4CH3.

Elektrophil einführbare Reste T sind z. B. cl, Br, NO, NO2, CHO, CN oder Acylreste, wobei Acylreste z. B. CH3CO, C2H5CO, CSH5CO. CH3SO2, C2H5S02 oder C6H5S02 sind.Residues T which can be introduced electrophilically are, for. B. cl, Br, NO, NO2, CHO, CN or acyl radicals, where acyl radicals z. B. CH3CO, C2H5CO, CSH5CO. CH3SO2, C2H5S02 or C6H5S02 are.

Als Alkylreste für T sind z. B. CH3, C2Hs, C3H7 oder C4H9 ZU nennen.As alkyl radicals for T are, for. B. CH3, C2Hs, C3H7 or C4H9 to name.

Reste Y sind im einzelnen neben den bereits genannten z. B.: CH3CO, C2H5CO, C3H7CO, C4H9CO, C5Hj1CO, C7H15C°. Y are in detail in addition to the z. E.g .: CH3CO, C2H5CO, C3H7CO, C4H9CO, C5Hj1CO, C7H15C °.

C6H5CO, CH3C6H4CO, ClC6H4CO, (CH3)2C6H3CO, H3COC6H4CO, Cl2C6H3CO, CH3S02, C2H5SO2, C4H9S02, C6H5SO2, CH3C6H4SO2, ClC6H4SO2, COOCH31 COOC2Hs, COOC3H7, COOC4H9, COOC6H13, COOC8H17. C6H5CO, CH3C6H4CO, ClC6H4CO, (CH3) 2C6H3CO, H3COC6H4CO, Cl2C6H3CO, CH3S02, C2H5SO2, C4H9S02, C6H5SO2, CH3C6H4SO2, ClC6H4SO2, COOCH31 COOC2Hs, COOC3H7, COOC4H9, COOC6H13, COOC8H17.

COOC2H40CH3, COOC2H4OC2HS COOC2H4OC4H9. COOC6Hs, COOC6H4CH3, CONH2, CONHCH3, CONHC2HS, CONHC4H9, CONHC6H13, CONHC8H17, CON(CH3)2, CON(C2H5?2. CON(C4H9)2, Methylenaktive Verbindungen der Formel H2T1 sind beispielsweise Verbindungen der Formel wobei Z Cyan, Nitro, Alkanoyl, Aroyl, Alkylsulfonyl, Arylsulfonyi, Carboxyl, Carbonester oder gegebenenfalls substituiertes Carbamoyl ist, sowie die Verbindungen der Formeln: Einzelne besonders wichtige Verbindungen der Formel sind z.B.: H2C(CN)2, sowie Die Kupplungskomponenten der Formel HK-stammen vorzugsweise aus der Anilin-, a-Naphthylamin-, Pyrazol-, Aminopyrazol-, Indol-, Thiazol-, Thiophen-, Phenol-, Naphthol-, Tetrahydrochinolin, Pyridon- oder Pyridinreihe, wobei solche der Anilin-, Pyrazol-, Thiophen- oder Thiazolreihe bevorzugt sind.COOC2H40CH3, COOC2H4OC2HS COOC2H4OC4H9. COOC6Hs, COOC6H4CH3, CONH2, CONHCH3, CONHC2HS, CONHC4H9, CONHC6H13, CONHC8H17, CON (CH3) 2, CON (C2H5? 2. CON (C4H9) 2, Examples of methylene-active compounds of the formula H2T1 are compounds of the formula where Z is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyi, carboxyl, carbon ester or optionally substituted carbamoyl, as well as the compounds of the formulas: Individual particularly important compounds of the formula are for example: H2C (CN) 2, as The coupling components of the formula HK- preferably come from the aniline, α-naphthylamine, pyrazole, aminopyrazole, indole, thiazole, thiophene, phenol, naphthol, tetrahydroquinoline, pyridone or pyridine series, with those of the aniline -, pyrazole, thiophene or thiazole series are preferred.

Die Kupplungskomponenten HK entsprechen insbesondere den allgemeinen Formeln wobei R1 Wasserstoff, Alkyl, Aralkyl oder Aryl, R2 Wasserstoff oder R3, R3 gegebenenfalls substituiertes Alkyl, Cycloalkyl, Alkenyl, Aralkyl oder Aryl, R4 und Rs unabhängig voneinander Wasserstoff, Alkyl, Alkoxy, Phenoxy, Halogen, Alkylsulfonylamino, Dialkylaminosulfonylamino oder Acylamino, R6 Cyan, Carbamoyl, Nitro oder Carbalkoxy und R7 gegebenenfalls substituiertes Phenyl, Alkyl, Aralkyl, Halogen, substituiertes Hydroxy oder Mercapto sind.The coupling components HK correspond in particular to the general formulas where R1 is hydrogen, alkyl, aralkyl or aryl, R2 is hydrogen or R3, R3 is optionally substituted alkyl, cycloalkyl, alkenyl, aralkyl or aryl, R4 and Rs are independently hydrogen, alkyl, alkoxy, phenoxy, halogen, alkylsulfonylamino, dialkylaminosulfonylamino or acylamino, R6 Cyano, carbamoyl, nitro or carbalkoxy and R7 are optionally substituted phenyl, alkyl, aralkyl, halogen, substituted hydroxy or mercapto.

Einzelne Reste R1 sind neben den bereits genannten beispielsweise Methyl, Ethyl, Propyl, Butyl, Benzyl, Phenethyl,. Phenyl, o-, m-, p-Tolyl oder o-, m-, p-Chlorphenyl.Individual radicals R1 are, in addition to those already mentioned, for example Methyl, ethyl, propyl, butyl, benzyl, phenethyl ,. Phenyl, o-, m-, p-tolyl or o-, m-, p-chlorophenyl.

Reste R3 sind neben den bereits genannten z.B. C1- bis C6-Alkylgruppen, die durch Chlor, Brom, Hydroxy, C1- bis C8-Alkoxy, Phenoxy, Cyan, Carboxy, C1- bis C8-Alkanoyloxy, C1- bis C8-Alkoxy-C1-C4-alkoxy, Benzoyloxy, o-, m-, p-Methylbenzoyloxy, o-, m-, p-Chlorbenzoyloxy, C1- bis C8-Alkoxyalkanoyloxy, Phenoxyalkanoyloxy, Cj- bis Ca-Alkoxycarbonyloxy, C1- bis Co-Alkoxyalkoxycarbonyloxy, Benzyloxycarbonyloxy, Phenethyloxycarbonyloxy, Phenoxyethoxycarbonyloxy, C1 - bis C8-Alkylaminocarbonyloxy, Cyclohexylaminocarbonyloxy, Phenylaminocarbonyloxy, C1- bis Ce-Alkoxycarbonyl, C1- bis C8-Alkoxyalkoxycarbonyl, Phenoxycarbonyl, Benzyloxycarbonyl, Phenoxy-C1-C4-alkoxy oder Phenethyloxycarbonyl substituiert sein können sowie Phenyl, Benzyl, Phenethyl oder Cyclohexyl.R3s are in addition to the already mentioned e.g. C1- to C6-alkyl groups, by chlorine, bromine, hydroxy, C1- to C8-alkoxy, phenoxy, cyano, carboxy, C1- to C8-alkanoyloxy, C1- to C8-alkoxy-C1-C4-alkoxy, benzoyloxy, o-, m-, p-methylbenzoyloxy, o-, m-, p-chlorobenzoyloxy, C1- to C8-alkoxyalkanoyloxy, phenoxyalkanoyloxy, Cj- to Ca-alkoxycarbonyloxy, C1- to Co-alkoxyalkoxycarbonyloxy, benzyloxycarbonyloxy, Phenethyloxycarbonyloxy, phenoxyethoxycarbonyloxy, C1 - to C8-alkylaminocarbonyloxy, Cyclohexylaminocarbonyloxy, phenylaminocarbonyloxy, C1- to Ce-alkoxycarbonyl, C1- to C8-alkoxyalkoxycarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenoxy-C1-C4-alkoxy or phenethyloxycarbonyl and phenyl, benzyl, phenethyl or cyclohexyl.

Einzelne Reste R3 sind z.B. Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Allyl, Methallyl, 2-Chlorethyl, 2-Bromethyl, 2-Cyanethyl, 2-Hydroxyethyl, 2-Phenyl-2-hydroxyethyl, 2,3-Dihydroxypropyl, 2-Hydroxypropyl, 2-Hydroxybutyl, 2-Hydroxy-3-phenoxypropyl, 2-Hydroxy-3-methoxypropyl, 2-Hydroxy-3-butoxypropyl, 3-Hydroxypropyl, 2-Methoxyethyl, 2-Ethoxyethyl, 2-Propoxyethyl, 2-Butoxyethyl, 2-Phenoxyethyl, 2-Phenoxypropyl, 2-Acetoxyethyl, 2-Propionyloxyethyl, 2-Butyryloxyethyl, 2-Isobutyryloxyethyl, 2-Methoxymethylcarbonyloxyethyl, 2-Ethoxymethylcarbonyloxyethyl, 2-Phenoxymethylcarbonyloxyethyl, 2-Methoxycarbonyloxyethyl, 2-Ethoxycarbonyloxyethyl, 2-Propoxyzarbonyloxyethyl, 2-Butoxycarbonyloxyethyl, 2-Phenyloxyzarbonyloxyethyl, 2-Benzyloxycarbonyloxyethyl, 2-Methoxyethoxycarbonyloxyethyl, 2-Ethoxyethoxycarbonyloxyethyl, 2-Propoxyethoxycarbonyloxyethyl, 2-Butoxyethoxycarbonyloxyethyi, 2-Methylaminocarbonyloxyethyl, 2-Ethylaminocarbonyloxyethyl, 2-Propylaminocarbonyloxyethyl, 2-Butylaminocarbonyloxyethyl, 2-Methoxycarbonylethyl, 2-Ethoxycarbonylethyl, 2-Propoxycarbonylethyl, 2-Butoxyzarbonylethyl, 2-Phenoxycarbonylethyl, 2-Benzyloxycarbonylethyl, 2-ß-Phenylethoxycarbonylethyl, 2-Methoxyethoxycarbonylethyl, 2-Ethoxyethoxy-carbonylethyl, 2-Propoxyethoxycarbonylethyl, 2-Butoxyethoxycarbonylethyl, 2-Phenoxyethoxycarbonylethyl oder 2-Benzoylethyl.Individual radicals R3 are e.g. methyl, ethyl, propyl, butyl, pentyl, Hexyl, allyl, methallyl, 2-chloroethyl, 2-bromoethyl, 2-cyanoethyl, 2-hydroxyethyl, 2-phenyl-2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl, 2-hydroxybutyl, 2-hydroxy-3-phenoxypropyl, 2-hydroxy-3-methoxypropyl, 2-hydroxy-3-butoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2-phenoxypropyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-isobutyryloxyethyl, 2-methoxymethylcarbonyloxyethyl, 2-ethoxymethylcarbonyloxyethyl, 2-phenoxymethylcarbonyloxyethyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxyzarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2-phenyloxyzarbonyloxyethyl, 2-benzyloxycarbonyloxyethyl, 2-methoxyethoxycarbonyloxyethyl, 2-ethoxyethoxycarbonyloxyethyl, 2-propoxyethoxycarbonyloxyethyl, 2-butoxyethoxycarbonyloxyethyi, 2-methylaminocarbonyloxyethyl, 2-ethylaminocarbonyloxyethyl, 2-propylaminocarbonyloxyethyl, 2-butylaminocarbonyloxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-butoxycarbonylethyl, 2-phenoxycarbonylethyl, 2-benzyloxycarbonylethyl, 2-ß-phenylethoxycarbonylethyl, 2-methoxyethoxycarbonylethyl, 2-ethoxyethoxycarbonylethyl, 2-propoxyethoxycarbonylethyl, 2-butoxyethoxycarbonylethyl, 2-phenoxyethoxycarbonylethyl or 2-benzoylethyl.

Als Reste R4 und R5 kommen beispielsweise Wasserstoff, Methyl, Ethyl, Propyl, Brom, Chlor, Methoxy, Ethoxy, Phenoxy, Benzyloxy, C1- bis C6-Alkanoylamino, Benzylamino sowie C1- bis C4-Alkylsulfonylamino oder -Dialkylaminosulfonylamino in Betracht.The radicals R4 and R5 are, for example, hydrogen, methyl, ethyl, Propyl, bromine, chlorine, methoxy, ethoxy, phenoxy, benzyloxy, C1- to C6-alkanoylamino, Benzylamino and C1 to C4 alkylsulfonylamino or dialkylaminosulfonylamino into consideration.

Reste 6 sind neben den bereits genannten z.B. Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Ethylaminocarbonyl, Diethylaminocarbonyl, Methoxycarbonyl, Ethoxycarbonyl, n- und i-Propoxycarbonyl, n-, i- und sek.-Butoxycarbonyl, Methoxyethoxycarbonyl, Ethoxyethoxycarbonyl, n- und i-Propoxyethoxycarbonyl oder n-, i- und sek.-Butoxyethoxycarbonyl.Residues 6 are in addition to those already mentioned e.g. aminocarbonyl, methylaminocarbonyl, Dimethylaminocarbonyl, ethylaminocarbonyl, diethylaminocarbonyl, methoxycarbonyl, Ethoxycarbonyl, n- and i-propoxycarbonyl, n-, i- and sec-butoxycarbonyl, methoxyethoxycarbonyl, Ethoxyethoxycarbonyl, n- and i-propoxyethoxycarbonyl or n-, i- and sec-butoxyethoxycarbonyl.

Reste R7 sind beispielsweise C1- bis Cro-Alkyl, C1- bis Cro-Alkoxy, Phenoxy, Benzyloxy, Phenyl, Chlor, Brom, Nitro, C1- bis C4-Alkoxycarbonyl, C1-bis C4-Mono- oder Dialkylamino, C1- bis C4-Alkoxy-ethoxy, C1- bis C4Alkyl-oder Phenylmercapto, C1- bis Cs-Alkanoylamino, wie Acetylamino, Propionylamino, Butyrylamino oder Valerylamino, ein- oder mehrfach substituiertes Phenyl, C1- bis C4-Alkyl, C1- bis C4-Alkoxycarbonylmethyl, Cyanmethyl oder Benzyl.R7s are, for example, C1- to Cro-alkyl, C1- to Cro-alkoxy, Phenoxy, benzyloxy, phenyl, chlorine, bromine, nitro, C1- to C4-alkoxycarbonyl, C1-bis C4-mono- or dialkylamino, C1- to C4-alkoxy-ethoxy, C1- to C4-alkyl or phenyl mercapto, C1- to Cs-alkanoylamino, such as acetylamino, propionylamino, butyrylamino or valerylamino, mono- or polysubstituted phenyl, C1- to C4-alkyl, C1- to C4-alkoxycarbonylmethyl, Cyanomethyl or benzyl.

Die Verbindungen der Formel 1 haben gelbe bis türkisfarbene Farbtöne und eignen sich insbesondere zum Färben von Polyester, Polyamiden, Celluloseestern und Mischgeweben aus Polyestern und Cellulosefasern. Man erhält Färbungen mit in der Regel guten bis sehr guten Echtheiten insbesondere auf Polyestern.The compounds of formula 1 have yellow to turquoise shades and are particularly suitable for dyeing polyesters, polyamides and cellulose esters and blended fabrics made from polyesters and cellulose fibers. One obtains colorations with in generally good to very good fastness properties, especially on polyesters.

Bei geeigneter Konstitution sind die Farbstoffe auch alkalich ätzbar.With a suitable constitution, the dyes can also be etched using alkali.

Die Herstellung der Verbindungen der Formel I kann nach an sich bekannten Methoden erfolgen. Einzelheiten können den Beispielen entnommen werden, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen.The compounds of the formula I can be prepared according to known methods Methods are done. Details can be found in the examples in which Information about parts and percentages is based on weight, unless otherwise stated relate.

Von besonderer Bedeutung sind Verbindungen der Formeln I a und 1 b in denen Xt Chlor, Brom, gegebenenfalls substituiertes Hydroxy oder Mercapto, y2 Cyan, Carbonester oder substituiertes Carbamoyl, T2 Formyl, Nitro, Cyan, z2 Cyan, Carbonester oder substituiertes Carbamoyl und K1 der Rest einer Kupplungskomponente der Anilin-, Thiazol-, Pyrazol-, Thiophen- oder Pyridinreihe sind.Compounds of the formulas I a are of particular importance and 1 b in which Xt chlorine, bromine, optionally substituted hydroxy or mercapto, y2 cyano, carbon ester or substituted carbamoyl, T2 formyl, nitro, cyano, z2 cyano, carbon ester or substituted carbamoyl and K1 the remainder of a coupling component of the aniline, thiazole, pyrazole , Thiophene or pyridine series.

Technisch besonders wertvoll sind Verbindungen der Formeln I a und I b, bei denen X1 Chlor, Ethoxy oder Phenylmercapto, y2 Cyan, T2 Formyl, z2 Cyan, Carbonester oder substituiertes Carbamoyl und K der Rest einer Kupplungskomponente der Anilin-, Thiazol, Thiophen oder Pyridinreihe sind.Compounds of the formulas I a and I are particularly useful from a technical point of view I b, where X1 is chlorine, ethoxy or phenylmercapto, y2 is cyano, T2 is formyl, z2 is cyano, Carbon ester or substituted carbamoyl and K is the remainder of a coupling component are of the aniline, thiazole, thiophene or pyridine series.

Beispiel 1 4,7 Teile 2-Amino-4-chlor-3-cyan-5-formyl-thiophen wurden bei maximal 30 OC in 30 Vol.-Teilen 85 %iger Schwefelsäure angerührt. Nach dem Zutropfen von 8,3 Teilen Nitrosylschwefelsäure (11,5 % N203) bei 0 - 5 OC wurde bei dieser Temperatur 4 Stunden gerührt.Example 1 4.7 parts of 2-amino-4-chloro-3-cyano-5-formyl-thiophene were at a maximum of 30 ° C. in 30 parts by volume of 85% sulfuric acid. After dropping of 8.3 parts of nitrosylsulfuric acid (11.5% N203) at 0-5 OC was in this Stirred temperature for 4 hours.

Die so erhaltene Diazoniumsalzlösung ließ man bei 0 °c in eine Lösung von 5,8 Teilen N,N-Diallyl-3-amino-acetanilid in einer Mischung aus 25 Vol.-Teilen DMF, 125 Teilen Wasser, 300 Teilen Eis, 20 Vol.-Teilen 32 %iger Salzsäure und 0,5 Teilen Amidosulfonsäure langsam einfließen. Nach Beendigung der Kupplung wurde der Farbstoff abgesaugt, neutral gewaschen und getrocknet. Man erhielt 9 Teile des Farbstoffs der Formel der Polyesterfasern in blauen, echten Nuancen färbt.The diazonium salt solution obtained in this way was left at 0 ° C. in a solution of 5.8 parts of N, N-diallyl-3-amino-acetanilide in a mixture of 25 parts by volume of DMF, 125 parts of water, 300 parts of ice, 20 parts by volume . -Parts of 32% hydrochloric acid and 0.5 part of sulfamic acid slowly flow in. After the coupling had ended, the dye was filtered off with suction, washed neutral and dried. 9 parts of the dye of the formula were obtained which dyes polyester fibers in real blue shades.

Beispiel 2 4,7 Teile2-Amino-4-chlor-3-cyan-5-forniylthiophen wurden analog Beispiel 1 diazotiert. Die Diazoniumsalzlösung wurde bei 0 OC in eine Lösung von 8,8 Teilen o-(Bisacetoxethyl)-amino-p-acetanisidin in einer Mischung aus 125 Teilen Wasser, 350 Teilen Eis, 1 Teil 96 %iger Schwefelsäure und 0,5 Teile Amidosulfonsäure eingetropft. Nach Beendigung der Kupplung wurde der Farbstoff abgesaugt, neutral gewaschen und getrocknet. Man erhielt 9,5 Teile eines grünschwarzen Pulvers der Formel das Polyestergewebe in echten, grünstichig blauen Tönen färbt.Example 2 4.7 parts of 2-amino-4-chloro-3-cyano-5-formylthiophene were diazotized analogously to Example 1. The diazonium salt solution was added dropwise at 0 ° C. to a solution of 8.8 parts of o- (bisacetoxethyl) amino-p-acetanisidine in a mixture of 125 parts of water, 350 parts of ice, 1 part of 96% strength sulfuric acid and 0.5 part of sulfamic acid . After the coupling had ended, the dye was filtered off with suction, washed neutral and dried. 9.5 parts of a green-black powder of the formula were obtained dyes the polyester fabric in real, greenish blue tones.

Analog den Beispielen 1 - 2 erhält man die in der folgenden Tabelle gekennzeichneten Farbstoffe. Bsp. T X Y -K Farbung auf Nr. Palyester 3 CHO C1 CN zuCNC2H5)2 )=/ 4 CHO C1 CN e N{C2Hs)2 blauviolett 5 CHO C1 CN > (C2Hs)2 blau CH3 6 CHO C1 CN 9 CNC2H40COCH3)2 blau NHCOCH3 7 CHO C1 CN 9 (C2H40COCHu)2 blau HHC O C2H4CN 8 CHO Cl CN < ,C2H4CN blau )e/ CH2CH=CH2 HNCOCH3 C2H4CN 9 CHO C1 CN > ,C2H4CN blau )r/ CHZCH=CH2 HNCO < U 10 CHO C1 CN > ,C2H4CN blau 10 CHO C1 CNN/C2HeCN blau HNCO 9 v l Bsp. T X Y -K Färbung auf Nr. j Polyester ,CH2CH=CH2 11 CHO Cl CN 9 N-CH2CH=CH2 rotstichig blau blau CH3 12 CHO Cl CN > ,C2H4CN blau - rotstichig CH3 CH3 13 CHO Cl CN 9 C2Hs blauviolett 25 14 CHO Cl CN < C2H4CN violett OCH3 15 CHO Cl CN - ~-N(C2Hsl2 türkis NHCOCH3 OCH2 16 CHO Cl CN + NHC2H4CO2CH3 turkis )=J OCH3 17 CHO Cl CN + C2H4CÑ turkis NHCOCH3 OCH3 18 CHO Cl CN 4 N(CH2CH=CH2)2 turkis NHCOCH3 OCH3 C2H4OH 19 1 CHO Cl CN > C2H4CN türkis NHCOCH3 OCH3 2Q CHO Cl CN + NHC2H4CN grünstichig blau NHCOCH3 Bsp. T X ~ ~ ~ ~ ~ ~ ~ Fãrbung auf -Nr. Polyester 21 CHO Cl CN > N(C2H4oCoCH3)2 grünstichig - CHO C1 CN blau OCH3 OCH3 22 CHO Cl CN > N(C2H40COCH3)2 blau CH3 23 CHO Cl CN zuN(C4H9)2 blau NHCOCH3 24 CHO I Cl CO2C Hs N(C6HI3)2 blau NHCOCH3 25 CHO Cl CM zuN(C4Hg)2 blau CH3 26 CHO Cl CN N(C2H5)2 blau OCH3 27 CHO Cl CM zuM(C2H5)2 blau NHS02CH3 OCH3 28 CHO Cl CM H(C2H5)2 blau OCH3 29 CHO C1 CN /C2Hr blau Y CHO Cl CM blau CH3 II 0 CH3 30 CHO Cl CN > HC2H4CO2CH3 blau CH3 Bsp. T X Y -K Färbung auf Nr. Polyester 31 1 CHO Cl COOCH3 4 {C2H5)2 blau CH3 32 CNO Cl SO2CH3 9 M(C4HS)2 blau NHCOCH3 C2H4CM 33 CHO Cl CONH2 < ,CZH4CN rotstichig C2Hs blau C113 34 CIiO C1 COM(CH32 > N(C2H40COCH3)2 blau NHCOCH3 35 CHO Cl CO2C2H5 ½j/(C2H.5)2 blau NHCOCH3 36 CHO C1 cO2C2H5 o N(C2HS>2 blauviolett 37 CHO Cl C02C2Hs zuN(C4Hgl2 blau CH3 NOCH3 C2H4CM 38 CHO Cl CO2C2Hs ~<t x>~N grünstichig )=/ CH2CH=CH2 blau NHCOCH3 C2H4CM 39 CNO 8r CM zu N,C2H4CN violett C2Hs 40 CHO Br CN zu,C2H4CN blauviolett C2Hs CH3 41 CHO ar CN < N(C2Hs)2 blau NHCOCH3 Ssp. T X -K fãrbung auf Nr. ~ . polyester OCH3 42 42 CHO Br CM > N{C2H40COCH3)2 grünstichig - blau NHCOCH3 43 CNO Br C02CzHs zuN(CH2CH=CH2)2 blau NHCOCH3 44- CHO F CNN(CZHs)2 blau NHCOCH3 45 CHO F CN o NtC2Hs)2 rots tichig blau 46 CHO F CN - N(CH2CH=CH2)2 blau CH3 47 CHO F C02C2Hs ,MCH2CH=CH2 rotstichig 2H4CN blau 48 CllO Cl C02C2H5 9 N(C2Hs)2 blau NHCOCH3 49 CHO Cl CONH2 9 N(C2Hs)2 f blau CH3 50 CHO Cl NO2 9 C2Hs blau NHCOCH3 51 CHO Cl CON(CH3)2 zuN(C2Hs)2 blau CH3 52 CHO Cl 502CH3 9 C2Hs blau CH3 Bsp. T X Y -K Färbung auf Nr. Polyester 53 CHO 8r C02C2HS ,C2H4CN 53 CHO Sr CO2C2HS 1NC2H5 blau CH3 54 CHO Cl CN vor blau blau ll3C 55 CHO Cl CN -N ( C2H5 2 blau S'N(C2H52 56 CHO Br CM ¼½SM ( C4H9) 2 blau H3C CM 57 CHO C1 CN + HC4Hg violett NHC4Hs 58 CHO Cl CN 8NHC2Hs blau 1 59 CHO C1 C02C2Hg 5S CHO Cl CO2C2H5 + HC2HxOH blau @ 60 CHO Cl CN ii--GfCHs gelbbraun $1) 61 CHO Cl CN ii rot H 2NN1-N IH24 BSPE T X ~ ~ ~ FarbUn9 RUf Nr. PO1YeSter 62 CHO C1 CN ^9r rot CH3 63 CHO C1 CNli,/CH3 blau CH3 COM 64 CKO C1 CN S N Msi blau N1 65 CHO Br CN ¾s1CM blau NC 66 CllO C1 CN 1I 11 blau 95 ^N(C4H9)2 67 CHO C1 CM w ;3F-NS SO violett 68 CiiO C1 CN OH 3F-OH rot OH 69 CHO C1 CN i%O;; rot I O Bsp. T X Y -K Färbung auf Nr. Polyester 70 CHO Cl CN o N 9 blau CaHs 71 CH(1 Cl CN o N / Nst CH3 blau H3 X CH3 C2H5 72 H Cl CM CN/CPHS rot CH3 73 -CH3 Cl CN > N(C2Hs)2 rot NHCOCH3 74 CH3 Cl CM 9 N{C2H5)2 rot CH3 OCH3 75 CH3 Cl CN + N(CH2CH2OCOCH3)2 rotviolett NHCOCH3 C2H5 76 C2H5 Cl CN < ,C2Hs rot CH3 C2H5 7? CH3 8r CM < ,C2Hs rot CH3 78 CN Cl CM 9 CNN(C2H5)2 blau CH3 79 CN Cl CN zuM(C2H4OCOCH3?2 blau ~ NHCOCH3 ~ Bsp. T X Y -K Färbung auf Nr. Polyester OCH3 80 CN Cl CM zuNtC2H40COCH3)2 türkis NHCOCH3 81 CN Br CM o N(CH2CH=CH2)2 rotstichig - blau 82 CN Cl CN "k, blau (C2Hg)2 83 NO2 Cl CN o -LLN(C2HS)2 rotstichig blau C2Hs 8; No2 Cl CN C2Hs blau CH3 C2H5 85 M02 Cl CM < c2Hs blau C2Hs OCH3 86 N02 Cl CM 4 NlC2H40COCH3)2 grünstichig blau OCH3 87 CH3lCl- Cl CM < N(C2Hs)2 blau 0 1 NHCOCH3 88 N02 Br CM 4 N(C2Hs)2 blau CH3 89 NO2 Cl CM < 2 blau ~ . Sl(c2H5) 2 Bsp. T X Y -K Färbung auf Nr. Polyester 90 N02 Cl CN < blau N C2Hs)2 91 Br C1 CNa .~C2H5 jrn blaustichig C2H4CN rot CH3 OCH3 92 Br Cl CM zu (C2H4OCOCH3 >2 blauviolett OCH3 C2H5 93 8r Cl CM + ,C2Hs rot C2H4CM 94 6r Cl CM e N,C2H4CN rot 95 Br Cl CN < N(C2Hs)2 blauviolett II 96 Cl C1 CN 9 C2H4CN blaustichig :2HbCN rot CH3 - 97 Cl Cl CM 9 N(C2H40COCH3)2 rotstichig blau NHCOCH3 98 ßr Br CM ,C2Hs rotstichig Sa Br Br CN 9 NC2Hs blau NHCOCH3 Beispiel 99 11,7 Teile 2-Amino-3-cyan-4-ethoxy-5-formylthiophen wurden bei maximal 20 OC in 200 Vol.-Teilen Eisessig/Propionsäure (3 : 1) und 25 Vol.-Teilen 96 %iger Schwefelsäure angerührt. Bei 0 - 5 OC ließ man unter Rühren 23 Teile Nitrosylschwefelsäure (11,5 te N203) zutropfen und anschließend 1 Stunde rühren.The dyes identified in the table below are obtained analogously to Examples 1-2. E.g. TXY -K coloring on No. Palyester 3 CHO C1 CN to CNC2H5) 2 ) = / 4 CHO C1 CN e N (C2Hs) 2 blue-violet 5 CHO C1 CN> (C2Hs) 2 blue CH3 6 CHO C1 CN 9 CNC2H40COCH3) 2 blue NHCOCH3 7 CHO C1 CN 9 (C2H40COCHu) 2 blue HHC O C2H4CN 8 CHO Cl CN <, C2H4CN blue ) e / CH2CH = CH2 HNCOCH3 C2H4CN 9 CHO C1 CN>, C2H4CN blue ) r / CHZCH = CH2 HNCO < U 10 CHO C1 CN>, C2H4CN blue 10 CHO C1 CNN / C2HeCN blue HNCO 9 v l E.g. TXY -K staining No. j polyester , CH2CH = CH2 11 CHO Cl CN 9 N-CH2CH = CH2 reddish blue blue CH3 12 CHO Cl CN>, C2H4CN blue - reddish CH3 CH3 13 CHO Cl CN 9 C2Hs blue-violet 25th 14 CHO Cl CN <C2H4CN purple OCH3 15 CHO Cl CN - ~ -N (C2Hsl2 turquoise NHCOCH3 OCH2 16 CHO Cl CN + NHC2H4CO2CH3 turquoise ) = J OCH3 17 CHO Cl CN + C2H4CÑ turquoise NHCOCH3 OCH3 18 CHO Cl CN 4 N (CH2CH = CH2) 2 turquoise NHCOCH3 OCH3 C2H4OH 19 1 CHO Cl CN> C2H4CN turquoise NHCOCH3 OCH3 2Q CHO Cl CN + NHC2H4CN greenish blue NHCOCH3 E.g. TX ~ ~ ~ ~ ~ ~ ~ coloring on -No. polyester 21 CHO Cl CN> N (C2H4oCoCH3) 2 green-tinged - CHO C1 CN blue OCH3 OCH3 22 CHO Cl CN> N (C2H40COCH3) 2 blue CH3 23 CHO Cl CN to N (C4H9) 2 blue NHCOCH3 24 CHO I Cl CO2C Hs N (C6HI3) 2 blue NHCOCH3 25 CHO Cl CM zuN (C4Hg) 2 blue CH3 26 CHO Cl CN N (C2H5) 2 blue OCH3 27 CHO Cl CM zuM (C2H5) 2 blue NHS02CH3 OCH3 28 CHO Cl CM H (C2H5) 2 blue OCH3 29 CHO C1 CN / C2Hr blue Y CHO Cl CM blue CH3 II 0 CH3 30 CHO Cl CN> HC2H4CO2CH3 blue CH3 E.g. TXY -K staining No. polyester 31 1 CHO Cl COOCH3 4 (C2H5) 2 blue CH3 32 CNO Cl SO2CH3 9 M (C4HS) 2 blue NHCOCH3 C2H4CM 33 CHO Cl CONH2 <, CZH4CN reddish C2Hs blue C113 34 CIiO C1 COM (CH32> N (C2H40COCH3) 2 blue NHCOCH3 35 CHO Cl CO2C2H5 ½j / (C2H.5) 2 blue NHCOCH3 36 CHO C1 cO2C2H5 o N (C2HS> 2 blue-violet 37 CHO Cl C02C2Hs zuN (C4Hgl2 blue CH3 STILL3 C2H4CM 38 CHO Cl CO2C2Hs ~ <t x> ~ N tinted green ) = / CH2CH = CH2 blue NHCOCH3 C2H4CM 39 CNO 8r CM to N, C2H4CN purple C2Hs 40 CHO Br CN to, C2H4CN blue-violet C2Hs CH3 41 CHO ar CN <N (C2Hs) 2 blue NHCOCH3 Ssp. TX -K coloring on No. ~. polyester OCH3 42 42 CHO Br CM> N {C2H40COCH3) 2 greenish tinge - blue NHCOCH3 43 CNO Br C02CzHs zuN (CH2CH = CH2) 2 blue NHCOCH3 44- CHO F CNN (CZHs) 2 blue NHCOCH3 45 CHO F CN o NtC2Hs) 2 red tint blue 46 CHO F CN - N (CH2CH = CH2) 2 blue CH3 47 CHO F C02C2Hs, MCH2CH = CH2 reddish 2H4CN blue 48 CllO Cl C02C2H5 9 N (C2Hs) 2 blue NHCOCH3 49 CHO Cl CONH2 9 N (C2Hs) 2 f blue CH3 50 CHO Cl NO2 9 C2Hs blue NHCOCH3 51 CHO Cl CON (CH3) 2 to N (C2Hs) 2 blue CH3 52 CHO Cl 502CH3 9 C2Hs blue CH3 E.g. TXY -K staining No. polyester 53 CHO 8r C02C2HS, C2H4CN 53 CHO Sr CO2C2HS 1NC2H5 blue CH3 54 CHO Cl CN before blue blue ll3C 55 CHO Cl CN -N (C2H5 2 blue S'N (C2H52 56 CHO Br CM ¼½SM (C4H9) 2 blue H3C CM 57 CHO C1 CN + HC4Hg purple NHC4Hs 58 CHO Cl CN 8NHC2Hs blue 1 59 CHO C1 C02C2Hg 5S CHO Cl CO2C2H5 + HC2HxOH blue @ 60 CHO Cl CN ii - GfCHs yellow-brown $ 1) 61 CHO Cl CN ii red H 2NN1-N IH24 BSPE TX ~ ~ ~ FarbUn9 RUf No. PO1YeSter 62 CHO C1 CN ^ 9r red CH3 63 CHO C1 CNli, / CH3 blue CH3 COM 64 CKO C1 CN SN Msi blue N1 65 CHO Br CN ¾s1CM blue NC 66 CllO C1 CN 1I 11 blue 95 ^ N (C4H9) 2 67 CHO C1 CM w; 3F-NS SO purple 68 CiiO C1 CN OH 3F-OH red OH 69 CHO C1 CN i% O ;; Red IO E.g. TXY -K staining No. polyester 70 CHO Cl CN o N 9 blue CaHs 71 CH (1 Cl CN o N / Nst CH3 blue H3 X CH3 C2H5 72 H Cl CM CN / CPHS red CH3 73 -CH3 Cl CN> N (C2Hs) 2 red NHCOCH3 74 CH3 Cl CM 9 N {C2H5) 2 red CH3 OCH3 75 CH3 Cl CN + N (CH2CH2OCOCH3) 2 red-violet NHCOCH3 C2H5 76 C2H5 Cl CN <, C2Hs red CH3 C2H5 7? CH3 8r CM <, C2Hs red CH3 78 CN Cl CM 9 CNN (C2H5) 2 blue CH3 79 CN Cl CN zuM (C2H4OCOCH3? 2 blue ~ NHCOCH3 ~ E.g. TXY -K staining No. polyester OCH3 80 CN Cl CM to NTC2H40COCH3) 2 turquoise NHCOCH3 81 CN Br CM o N (CH2CH = CH2) 2 reddish - blue 82 CN Cl CN "k, blue (C2Hg) 2 83 NO2 Cl CN o -LLN (C2HS) 2 red-tinged blue C2Hs 8th; No2 Cl CN C2Hs blue CH3 C2H5 85 M02 Cl CM <c2Hs blue C2Hs OCH3 86 N02 Cl CM 4 NlC2H40COCH3) 2 green-tinged blue OCH3 87 CH3lCl- Cl CM <N (C2Hs) 2 blue 0 1 NHCOCH3 88 N02 Br CM 4 N (C2Hs) 2 blue CH3 89 NO2 Cl CM <2 blue ~. Sl (c2H5) 2 E.g. TXY -K staining No. polyester 90 N02 Cl CN <blue N C2Hs) 2 91 Br C1 CNa. ~ C2H5 jrn has a bluish cast C2H4CN red CH3 OCH3 92 Br Cl CM to (C2H4OCOCH3> 2 blue-violet OCH3 C2H5 93 8r Cl CM +, C2Hs red C2H4CM 94 6r Cl CM e N, C2H4CN red 95 Br Cl CN <N (C2Hs) 2 blue-violet II 96 Cl C1 CN 9 C2H4CN bluish tint : 2HbCN red CH3 - 97 Cl Cl CM 9 N (C2H40COCH3) 2 reddish tinged blue NHCOCH3 98 ßr Br CM, C2Hs reddish Sa Br Br CN 9 NC2Hs blue NHCOCH3 Example 99 11.7 parts of 2-amino-3-cyano-4-ethoxy-5-formylthiophene were added to 200 parts by volume of glacial acetic acid / propionic acid (3: 1) and 25 parts by volume of 96% strength sulfuric acid at a maximum of 20 ° C. touched. At 0-5 ° C., 23 parts of nitrosylsulfuric acid (11.5 N 2 O 3) were added dropwise with stirring, and the mixture was then stirred for 1 hour.

Die so erhaltene Diazoniumsalzlösung wurde bei 0 OC in eine Lösung von 21 Teilen o-(Bisacetoxethyl)-amino-p-acetanisidin in einer Mischung aus 100 Vol.-Teilen Dimethylformamid, 500 Teilen Wasser, 25 Vol.-Teilen 18 %iger Salzsäure, 250 Teilen Eis und 1 Teil Amidosulfonsäure getropft. Nach Beendigung der Kupplung wurde der Farbstoff abgesaugt, neutral gewaschen und getrocknet. Man erhielt 25 Teile des Farbstoffs der Formel das Polyesterfasern in grünstichig blauen, echten Nuancen anfärbt.The diazonium salt solution thus obtained was at 0 ° C. in a solution of 21 parts of o- (bisacetoxethyl) -amino-p-acetanisidine in a mixture of 100 parts by volume of dimethylformamide, 500 parts of water, 25 parts by volume of 18% hydrochloric acid, 250 parts of ice and 1 part of sulfamic acid were added dropwise. After the coupling had ended, the dye was filtered off with suction, washed neutral and dried. 25 parts of the dye of the formula were obtained that dyes polyester fibers in greenish blue, real nuances.

Analog Beispiel 99 wurden die in der folgenden Tabelle angegebenen Farbstoffe erhal-ten. Bsp. T X Y -K Färbung auf Nr. Polyester 100 CllO OC2H5 CN > N(C2Hs}2 blau NHCOCH3 101 CHO OCLHS CN o NlC2Hs)2 blauviolett 102 CllO oC2H5 CM 9 M(C2H5)2 blau CH3 103 CHO OC2HS CN < N(C2H40COCH3)2 blau NHCOCH3 104 CHO OC2Hs CM < ,C2H4CN blau HNCOCH3 C2 N4CN 105 CNO OC2Hs CN 2 C2H40COCH3 blau HNCO 4 106 CHO OC2Hs CN , > -CH2CH=CH2 rotstichig - rotstichig CH3 107 CHO oC2H5 CN > ,C2H4CN rotstichig C2H5 blau CH3 108 CHO OC2H5 CM < C2H5 blauviolett C2H4CN 109 CHO oC2H5 CM o ,C2H4CN violett C2 H4OCOCH3 Ssp. T X Y -K Färbung auf Nr. . Polyester OCH3 110 CHO OC2Hs CN -('N(C2Hs)2 turkis NHCOCH3 OCH3 111 CHO OC2H5 CN zuNHC2H4C02CH3 turkis NHCOCH3 OCH3 112 CHO oC2H5 CN < N(CH2CH=CH2)2 türkis NHCOCH3 OCH3 113 CHO OC2H5 CN zu N(C2H40COCH3)2 grünstichig - blau OCH3 blau OCH3 11; CHO oC2H5 CN > N{C2H40C°CH3)2 blau CH3 115 CHO OC2H5 C02C2H5 9 N(C6H13)2 blau NHCOCH3 116 CHO OC2Hs COOCH3 < N(C2Hs)2 blau CH3 117 CHO OC2H5 S02CH3 N(C4H9)2 blau NHCOCH3 C2H4CM 118 CHO OC2Hs CONH2 < N,C2HsCN rotstichig C2H5 blau CH3 119 CHO OC2Hg CoN(CH3)2 < N(C2H40COCH3)2 blau . ~ | NHCOCH3 ~ ~ ~ Bsp. T X Y -K Fãrbung auf Nr. Polyester 120 CNO OC2H5 CO2C2H5 9 N(C2Hs)2 blau NHCOCH3 121 CHO oC2Hs C02C2H5 o NtC2Hs)2 blauviolett 122 CHO oC2H5 C02C2H5 < NlC4Hg)2 blau CH3 123 CHO oc2Hs co2c2Hs @ MC2H4CM grünstichig CH2CH=CH2 blau NHCOCH3 124 CHO OCH3 CN o NC2H4CN violett 125 CHO OCH3 CN - ,CHGCN 125 CHO OCH3 CM 9 C2Hs blauviolett CH3 126 CHO OCH3 CN - \)-N(C2HS]2 blau NHCOCH3 OCH3 127 CHO OCH3 CN -(C2H*OCOCH3)2 grünstichig blau NHCOCH3 128 CHO OCH3 cozc2Hs a M(CH2CH=CH2)£ blau NHCOCH3 129 CHO OC6Hs CN > N(C2Hs)2 blau NHCOCH3 CH2CH=CH2 130 CHO OC6Hs | CM zu NoCH2CH=CH2 blauviolett I CzH4CN Bsp. T X Y -K Färbung auf Nr. Polyester 131 CHO SCsHs Co2c2Hs 9 M(C2H5>2 blau NHCOCH3 132 CllO Sc2Hs CM CNC2HGCN blauviolett C2HS 133 CHO SCsHs CN ,COH6CN I 133 CHO SCsHs CM MC2 H5 blau CH3 136 CHO OC2Hs CN 0 134 CHO oC2Hs CN <g blau H3C'I 135 CllO oC2H5 CN IIT-N blau 136 CHO oC2Hs CN < 2 blau H3C CM 137 CllO OC2H5 CN VNHC4H9 rotstichig blau NHC4H9 138 CHO OC2Hs CN zuNHC2Hs blau Y 139 CHO OCH3 C02C2Hs 4 NHC2H40H blau J> 140 CHO OC2H5 CM < CHs gelbbraun HO cN ¼ Bsp. T X Y -K Farbung auf Nr. Polyester t41 CHO oC2Hs CN N 2 N rot H2 Nlz2 4 142 CHO oC2H5 CN 4 M-CH3 rot CH3 CH3 143 CHO 0C2H5 CM blau CH3 i) CM 144 CHO oC2Hs CN (S + blau Miö 145 CHO OCH3 CM blau I I 146 CHO OC6HS CN (S X N(C4Hg)z 2 blau 14? CH3 OC2Hs CM 9 N(C2Hs)2 rot NHCOCH3 148 CH3 0c2Hs CN 9 -N(C2Hs)2 rot CH3 Bsp. T X Y -K Färbung auf Nr. Polyester OCH3 149 CH3 oC2H5 CN > N(CH2CH2oCoCH3)2 rotviolett MHCOCH3 C2H5 150 C2HS oC2H5 CN > ,C2Hs rot rot CM CH3 151 CH3 OC2H5 CN --N/C2Hf 151 CH3 OC2HS CM rot CH3 152 CN OC2HS CN C2H5) blau CH3 153 CN OC2Hs CN zuN(CzH40COCH3)2 blau MHCOCH3 C2H4CM 154 N02 OC2Hs CN 9 CH2CH=CH2 blau NHCOCH3 ~ Beispiel 155 5,8 Teile des in Beispiel 12 beschriebenen Farbstoffs wurden in 60 Vol.-Teilen Dioxan gelöst, mit 3,4 Teilen Cyanessigsäureethylester, 1 Teil Eisessig und 1 Teil-Piperidin versetzt und 16 Stunden bei Raumtemperatur gerührt. Anschließend wurden 50 Teile Wasser und 50 Teile Eis zugegeben. Es wurde 15 Minuten gerührt, das Produkt abgesaugt und neutral gewaschen.The dyes given in the table below were obtained analogously to Example 99. E.g. TXY -K staining No. polyester 100 CllO OC2H5 CN> N (C2Hs} 2 blue NHCOCH3 101 CHO OCLHS CN o NlC2Hs) 2 blue-violet 102 CllO oC2H5 CM 9 M (C2H5) 2 blue CH3 103 CHO OC2HS CN <N (C2H40COCH3) 2 blue NHCOCH3 104 CHO OC2Hs CM <, C2H4CN blue HNCOCH3 C2 N4CN 105 CNO OC2Hs CN 2 C2H40COCH3 blue HNCO 4 106 CHO OC2Hs CN,> -CH2CH = CH2 reddish - reddish CH3 107 CHO oC2H5 CN>, C2H4CN reddish C2H5 blue CH3 108 CHO OC2H5 CM <C2H5 blue-violet C2H4CN 109 CHO oC2H5 CM o, C2H4CN purple C2 H4OCOCH3 Ssp. TXY -K staining on No. . polyester OCH3 110 CHO OC2Hs CN - ('N (C2Hs) 2 turquoise NHCOCH3 OCH3 111 CHO OC2H5 CN to NHC2H4C02CH3 turquoise NHCOCH3 OCH3 112 CHO oC2H5 CN <N (CH2CH = CH2) 2 turquoise NHCOCH3 OCH3 113 CHO OC2H5 CN to N (C2H40COCH3) 2 greenish tint - blue OCH3 blue OCH3 11; CHO oC2H5 CN> N {C2H40C ° CH3) 2 blue CH3 115 CHO OC2H5 C02C2H5 9 N (C6H13) 2 blue NHCOCH3 116 CHO OC2Hs COOCH3 <N (C2Hs) 2 blue CH3 117 CHO OC2H5 S02CH3 N (C4H9) 2 blue NHCOCH3 C2H4CM 118 CHO OC2Hs CONH2 <N, C2HsCN reddish C2H5 blue CH3 119 CHO OC2Hg CoN (CH3) 2 <N (C2H40COCH3) 2 blue . ~ | NHCOCH3 ~ ~ ~ E.g. TXY -K coloring on No. polyester 120 CNO OC2H5 CO2C2H5 9 N (C2Hs) 2 blue NHCOCH3 121 CHO oC2Hs C02C2H5 o NtC2Hs) 2 blue-violet 122 CHO oC2H5 C02C2H5 <NlC4Hg) 2 blue CH3 123 CHO oc2Hs co2c2Hs @ MC2H4CM greenish CH2CH = CH2 blue NHCOCH3 124 CHO OCH3 CN o NC2H4CN purple 125 CHO OCH3 CN-, CHGCN 125 CHO OCH3 CM 9 C2Hs blue-violet CH3 126 CHO OCH3 CN - \) - N (C2HS] 2 blue NHCOCH3 OCH3 127 CHO OCH3 CN - (C2H * OCOCH3) 2 tinted green blue NHCOCH3 128 CHO OCH3 cozc2Hs a M (CH2CH = CH2) £ blue NHCOCH3 129 CHO OC6Hs CN> N (C2Hs) 2 blue NHCOCH3 CH2CH = CH2 130 CHO OC6Hs | CM to NoCH2CH = CH2 blue-violet I CzH4CN E.g. TXY -K staining No. polyester 131 CHO SCsHs Co2c2Hs 9 M (C2H5> 2 blue NHCOCH3 132 CllO Sc2Hs CM CNC2HGCN blue-violet C2HS 133 CHO SCsHs CN, COH6CN I 133 CHO SCsHs CM MC2 H5 blue CH3 136 CHO OC2Hs CN 0 134 CHO oC2Hs CN <g blue H3C'I 135 CllO oC2H5 CN IIT-N blue 136 CHO oC2Hs CN <2 blue H3C CM 137 CllO OC2H5 CN VNHC4H9 reddish blue NHC4H9 138 CHO OC2Hs CN to NHC2Hs blue Y 139 CHO OCH3 C02C2Hs 4 NHC2H40H blue J> 140 CHO OC2H5 CM <CHs yellow-brown HO cN ¼ E.g. TXY -K coloring on No. polyester t41 CHO oC2Hs CN N 2 N red H2 Nlz2 4 142 CHO oC2H5 CN 4 M-CH3 red CH3 CH3 143 CHO 0C2H5 CM blue CH3 i) CM 144 CHO oC2Hs CN (S + blue Miö 145 CHO OCH3 CM blue II 146 CHO OC6HS CN (SXN (C4Hg) z 2 blue 14? CH3 OC2Hs CM 9 N (C2Hs) 2 red NHCOCH3 148 CH3 0c2Hs CN 9 -N (C2Hs) 2 red CH3 E.g. TXY -K staining No. polyester OCH3 149 CH3 oC2H5 CN> N (CH2CH2oCoCH3) 2 red-violet MHCOCH3 C2H5 150 C2HS oC2H5 CN>, C2Hs red red CM CH3 151 CH3 OC2H5 CN --N / C2Hf 151 CH3 OC2HS CM red CH3 152 CN OC2HS CN C2H5) blue CH3 153 CN OC2Hs CN zuN (CzH40COCH3) 2 blue MHCOCH3 C2H4CM 154 N02 OC2Hs CN 9 CH2CH = CH2 blue NHCOCH3 ~ Example 155 5.8 parts of the dye described in Example 12 were dissolved in 60 parts by volume of dioxane, 3.4 parts of ethyl cyanoacetate, 1 part of glacial acetic acid and 1 part of piperidine were added and the mixture was stirred at room temperature for 16 hours. Then 50 parts of water and 50 parts of ice were added. The mixture was stirred for 15 minutes, and the product was filtered off with suction and washed neutral.

Nach dem Trocknen im vakuum bei 50 OC erhielt man 6,6 Teile des Farbstoffs der Formel der Polyesterfasern in mittelblauen Tönen färbt.After drying in vacuo at 50 ° C., 6.6 parts of the dye of the formula were obtained which dyes polyester fibers in medium blue tones.

Beispiel 156 5,1 Teile des in Beispiel 13 beschriebenen Farbstoffes wurden in 65 Volumenteilen Dioxan gelöst, mit 4,2 Teilen Cyanessigsäurebutylester, 1 Teil Eisessig und 1 Teil Piperidin versetzt und 16 Stunden bei Raumtemperatur gerührt. Anschließend wurden 50 Teile Wasser und 50 Teile Eis zugegeben, 1 Stunde gerührt, das Produkt abgesaugt und neutral gewaschen. Nach dem Trocknen wurden 5,9 Teile des Farbstoffs der Formel erhalten, der Polyester in echten blauen Tönen färbt.Example 156 5.1 parts of the dye described in Example 13 were dissolved in 65 parts by volume of dioxane, 4.2 parts of butyl cyanoacetate, 1 part of glacial acetic acid and 1 part of piperidine were added and the mixture was stirred at room temperature for 16 hours. Then 50 parts of water and 50 parts of ice were added, the mixture was stirred for 1 hour, and the product was filtered off with suction and washed neutral. After drying there was 5.9 parts of the dye of the formula that dyes polyester in real blue tones.

Analog den Beispielen 155 und 156 wurden die in der folgenden Tabelle aufgeführten Farbstoffe erhalten. Bsp. X Y y1 y2 -K Fãrbung Nr. auf PES 157 Cl CN COOC2Hs COOC2H5 zu,C2H4CN CH3 C2H4CM rot- 158 Cl CN COOC2H5 COOCzHs o C2H5 stichig C2H5 blau 159 Cl CN COOC2Hs COOC2H5 > N(C2Hs)2 blau OCH3 160 Cl CN COOC2Hs COOC2Hs < N(C4Hg)2 blau NHCOCH3 C2H5 161 Cl CN CN CN < ,C2H5 blau CH3 C2H5 162 Cl CN COCH3 COOC2H5 < C2H4CN blau CH3 163 Cl COOC2Hs CN COOC2H5 4 -(N(C2HS)2 blau 0 164 Cl cooc2Hs CM cOOC2Hs 9 N(C2H40CCH3 2 blau CH3 165 Cl COOC2H5 CN COOC2H5 < N{C2Hs)2 blau NHCOCH3 166 Cl C00C2ll5 COOC2H5 COOC2HS dunkel- 166 C1 COOC2Hs COOC2Hs COOC2Hs dunkel- CH3 Bsp. X Y t Y2 K -K Färbung Nr. auf PES C2H5 167 Cl COOC2H5 COCH3 C00C2115 N dunkel- - C1 COOC2Hs COCH3 COOC2HS C2HoCN blau CH3 168 Cl CooC2Hs COCH3 COCH3 9 C2H4CN blau CH3 C2HS 169 Cl COOC2HS COCH3 CN > oC2H5 dunkel- C2H 4CN blau C3 0 II C2H4CN 170 Cl C-NH2 CN COOCzHs , dunkel- CH2CH=CH2 blau CH3 0 171 Cl C-NH2 CN COOC2Hs 9 -N(C2Hs)2 blau )=/ C2H5 172 Cl so2CH3 CM COOC2Hs 9 oC2H5 dunkel- C C2H4CN blau CH3 173 Cl S02CH3 CN CQOC2Hs CH2CH=CH22 blau CH3 174 Cl S02CH3 CM COOC2HS N(C2Hs)2 blau MHCOCH3 )C/ NHCOCH3 175 Cl CN CN COOC2H5 e -=)2-N(C2H40CCH32 blau C2H4CM 176 Cl CM CM COOC2H5 MI dunkel- CH2CH=CHC blau CH3 Bsp. X Y1 y2 -K Fãrbung Nr. auf PCS 177 Cl CN CN COOC2H5 M II dunkel- C2H40CCH3 blau CH3 1 178 Cl CN i CN COOC2Hs 4 N dunkel- C2H4COO blau cH3 CH3 179 Cl CN CN COOC2H5N(C2HS)2 dunkel- - blau C113 180 Cl CM CM COOC2H5 dunkel- M(C4H9>2 blau CH3 181 Cl CN CM COOC2Hs 9 N(C2Hsl2 blau NHCOCH3 182 Cl CN CN COOC2H5 < S X N(C2Hs 2blau H3C CM 183 Cl CN CN COOC2Hs 4 NHC4Hg blau MHC4H9 184 Cl CN CN COOC2Hs - \)-N(C2Hs)2 blau MHSO2CH3 185 Cl CN CN COOC2H5 HO-N,N violett ¼ 186 Cl CN CN Cooc2Hs H2N l N-N violett CH Bsp. X Y y2 Y2 -K Färbung Nr. auf PES 187 Cl CN CN COOC2HS i /N-CH3 violett C CsH5 C2H4CN 188 Cl CM CN CONHCH3 ~< N dunkel- »== CH2CH=CH2 blau CH3 189 Cl CN CN CONHC2H5 > vC2H4CN dunkel- CH2CH=( blau CH3 C2H4CN 190 Cl CN CN S02CH3 v -41 dunkel- dunkel- CN3 191 Cl CN CN COCH3 4 N C2H4CM dunkel- . »=v CH2CH=CH2 blau CH3 192 Cl CN CN COOCH3 > ,C2H4CN dunkel- C CH2CH=CH2 blau CH3 193 Cl CM CM COOC4Hg(n < N(C4Hg}2 blau NHCOCH3 194 Cl CN CN COOC4H9(n 9 N(C2H5)2 blau NHCOCH3 195 Cl CN CN COOC4H9(n> NHCzH4COC4Hz w blau CH3 CM Cl CN CN COOC4H9(n) < C2Hs CH3 0 C2H5 197 Cl CN CN CO-NH M dunkel- 8 XC2H4CN blau CIi3 C2H5 198 Cl CN CN N zu XC2Hs dunkel- - - C2H4CM blau CH3 199 Cl CN CN CAN n v c2Hs dunkel- X \C2H4CN blau H CH3 /C2Hs 200 Cl CN CN CONH2 < M dunkel- C )r/ XC2H4CN blau CH3 201 Cl CM COOC2Hs COOC2HS < N{C4Hs)2 marine- blau ,CH2CH=CH2 202 Cl CN COCH3 COOC2Hs < NsCH2CH=CH2 dunkel- - C2H4OH blau CH3 ,CH2CH=CH2 202 Cl CM CM .CONHCH3 > NsCH2CH=CH2 dunkel- - C2H4OH blau CH3 ,C2H5 0 rot- 204 Br CN CN COOCzHs zu NxC2Hs Ii rotstichig uC2H40CCH3 blau ,C2Hs rot- 205 ßr CM CM COOC2Hs o C285 rotstichig \C2H4CN blau 206 8r CN CM COOC2Hs zuXCsH40CH3 blau *) Färbung auf Polyester Bsp. X Y VI Y2 -K Nr. dunkel- 207 Br CN CN coOC2Hs 9 N(C2Hs)2 blau H3C ,C2H4CN dunkel- 208 Br CN CN ' COOC2H5 H > XCH2CH=CH2 blau - CH2CH=CH2 H3C ,C2H4OCH3 dunkel- 209 i Br CN CN COOC2H5 9 XC2H4CN blau C2H4CM 113C 0 - II 0 210 Br CN CM COOC2H5 M(C2H4OCCH3>2 blau H3C ,C2H4CN dunkel- 211 Br CN CN COOC2Hs 4 N blau > C2H401CINHC Hs H3C CH3 4O0{INHCtH9une1 212 8 rBr CN CN COOC2Hg - HC2H4COOCH blau H3C ,C2H dunkel- 213 9r CM CM COOC4Hg(n < blau C2H4OCC2H H3C II 0 214 Br COOC2Hs CN CM a N(C2Hs)2 blau NHCOCH3 215 Sr COOC2H5 CM COOC2Hg 9 N(CzH40C2Hs blau N(C2H4OC2HS)2 dunkel- H3C 0 216 Br COOC2Hs CN CON!CNJ)2 N(CzH40CCH3 2 blau - violett *) Färbung auf Polyester w E s R E Bsp. X Y Y1 Y2 -K Nr. ,C2H4CM dunkel- 217 / 5r CONH2 CN COOC2Hs < XC2Hs blau H3C iH3C dunkel- 218 Br S02CH3 CN COOC2Hs > oC2H4CN blau H3C I \ oC2H4CN dunkel- 219 Br CON(CH3)2 CN COOC2H5 9 XC2Hs blau blau H3C CM 0 II dunkel- 220 Br CN CN cooc2Hs U NHC2H40CH3 dUbleal~ NHC2H40CH3 CH3O 221 Br CN CN COOC2Hs CH30 zu blau S N(l 2H5)2 222 Br CN CN COOCH3 zu blau S, N marine- 223 8r CM CN COOCH3 8NHC2HOH blau sC2H4CN dunkel- 224 Cl CN CN 4 > \CHzCH~CH2 blau H3C 225 F CN CN dunkel- 225 F CM CM COOC2H5 blau dunkel- 226 F CN CN COOC2Hs zuN(CH2CH=CH2 2 blau *) Färbung auf Polyester | - : Bsp. X Y y1 Y2 -K *) Nr. - 22? F CM CM C00C2H5 CO ,CN2CH=CH2 dunkel- J \C2HGCN ,CH2CH=CH2 dunkel- 228 F COOC2H5 CN COOC2Hs t3 blau blao oC2H4CN dunkel- 229 OC2H CM coOC2Hs COOC2HS a XCzHs blau >- LBXS H3C 230 OC2H5 CN COOC2Hs ClJoc2Hs z XC2H4CN dunkel- 231 OC2HT CN COOC2Hs COOC2H5 83N(C2H5)2 blau I OCHs 232 OC2H CM cOOCzHs COOCzHs NHCOCH3 blau NHCOCH3 ,C2Hs dunkel- 233 CM CN CN CN 83 XC2Ht,CN blau IN blau H3C ,C2Hs dunkel- 234 C2 CM COCH3 COOC2Hs 9 XC2H4CN blau OC2H C2H4CM NHCOCH3 235 CM COOC2H5 &i(C2HS>2 blau 235 OC2HS(COOC2Hs CN COOC2HS C2Hg)2 blau 236 CM COOC2H5 (C2ll4OCCll32 blau 236 0C2H|COOC2Hs CN )Y blau 237 - 0C2HslcOOc2Hs CN 1C00C2H5 NNCOCH3 l l NHCOCH3 *) Färbung auf Polyester Bsp. X Y Y2 -K Nr. C2H5 COOC2H5 COOC2H5 COOC2Hs /C2HJ dunkel- 238 OC2HlCOOC2H5 COOC2Hs cOOC2Hs $3 XC2H4CN blau H3C . XC2H5 dunkel- 239 OC2F1 |COOCZH5 COCH3 COOC2Hs H3C XC2H4CN blau \C2H4CN 240 OC2HlCOOC2H5 COCH3 COCH3 COCH3 » C2Hs violett H3C ,C2H5 OC2H(COOC2H5 COCH3 CN /C2H5 dunkel- 241 OC2HICOOC2Hs COCH3 CM < XC2HCN blau \C2HGCN 242 OC2HT C-MH2 CN COOC2Hs H3C N /C2H4CN blau H3C 243 OC2H C-NH2 CN COOC2Hs 43N(C2Hs}2 blau NHCOCH3 ,C2H5 dunkel- 244 OC2H S02CH3 CN COOC2Hs < XC2HxCN blau OC2H H3C H3C 245 0C2Hg; S02CH3 CM COOC2Hs vN(CH2CH=CH2 2 blau H3C 246 SO2CH3 CM COOC2Hs M(C2Hs>2 blau -| NHCOCH3 /C2H5 rotstichig NHCOCH3 24 7 OC2HT CN CN CON(CH3}2 < XC2H4CN -N blau j 248 OC2H5 CM CM COOC2Hs -N(C2H40CCH3)2 blau *) Färbung auf Polyester Bsp. X Y VI Y2 -K w w Nr. /C2HCN dunkel- OCH CzHiCN dunkel- 249 OC2H' CN CN COOC2H5 w blau \CH2CH=CHC, H3C /C2Hs 0 dunkel- 250 OC2H J CN CN COOC2Hs <t )-N 1 blau C2H4OCCH3 ,C2Hs dunkel- 251 OC2H CN CN COOCzH5 > blau XC2H4COOCH H3C 252 oC2H CM CM COOC2Hs g (C2H5)2 dUnbl ul- H3C dunkel- 253 OC2H; CN CN COOC2HsN(C4Hs)2 blau OC2H H3C blau 254 oc2 CN CN COOC2Hs 8 3 N(C2Hs)2 MHCOCH3 blau 255 OC2H CN CN COOC2Hs < S 1 N{C2H5) H3C CM 256 OC2H CN CN COOC2H5 WHC4H9 blau NHC4Hg 257 OC2H CN CN COOC4Hs ( n 9 N(C4Hg)2 blau NHCOCH3 258 OC2H CN CN COOC4Hg(n 9 N(C2H5>2 blau l | | NHCOCH3 l *) Färbung auf Polyester Bsp. X Y V1 Y2 -K *) Nr. 259 OC2H , CN CN COOC4Hgfn 33N(C2H4COOC41 19 blau H3C ,C2Hs dunkel- 260 OC2H ; CN CN COOC4H9(n < »N blau -C2H4COC2H 0C2H5 H3C 0 m x /c2Hs dunkel- 281 OC2H CM CN CoNH4> \> 4> 9N blau H3C ,C2H5 dunkel- 262 OC2H CM CM t3 aN blau H3C 263 OC2H CN CN dunkel- SN OC2H CM CM CMI N XC2H4CN blau H H3C n /c2Hs dunkel- 264 OC2H CM CM CONH2 \N\C2H4CN blau 2" \C2H4CN H3C marine- 265 OC2H; CN COOC2Hs COOC2Hs t3N(C4Hg) 2 blau t ,CH2CH=CH2 \ CH2CH=CH2 /CH2CH=CH2 dunkel- 265 OC2H CN COCH3 COOC2Hs <> \»N blau H3C /CH2CH=CH2 dunkel- 267 OC2 CN CN CONHCH3 nN blau H3C marine- 268 OC2H; CN CN COOC2Hs - vN(C2Hs)2 blau l NHS02CH3 *) Färbung auf Polyester Bsp. X | Y y1 y2 -K t) Nr. 269 OC2H CN CN COOC2Hs HO < violett ¼ E 270 OCzH CN CN Cooc2Hs N < violett I 271 OC2H CN CN COOC2HS violett tCSCH3 blau 272 Z CM C2H4CN N/CN24c11Cc2 dunkel- O&2H CM H3C H?C 273 OC2H5 CM CM ' COMHC2HS XCzH4CN dunkel- OC2H - blau DISC H3C 274 Of2H CM CM SO2CH3 /C2H6CN blau 27; OC2H - CN CH2CH=CH2 H3C -s sCzH4CN dunkel- 275 OCH CM CM COCH3 9 XCH2CH=CH2 blau OC2HJ H3C ,C2H4CN dunkel- 276 OC2H5 CN CN COOCH3 /C2H4CN dunke- I H3C 271 OCH3 CN OOCZHSC2Hg 0 277 OCH3 CN CN COOC2Hs o SC2Hs II blau- C2H4OCCH3 violett *) Färbung auf Polyester 278 OC6H CN CN cooc2Hs T XC2H4CN violett ,C2H5 279 SC6H CN CM COOC2HS C2Hs blau- 4 XC2H40CH3 violett dunkel- 280 SC6H CN CN COOC2Hs vN(C2Hs)2 blau H3C /C2H4CN dunkel- 281 OCH3 CM CM COOC2Hs 83 XCH2CH=CH2 blau H3C CH3 0 282 OCH3 CM CM COOC2H5 H$½\N HC2H4COO blau H3C 283 OCH3 CM CM COOC4Hg(n 83 xC2Hs blau H3C I) 0 dunkel- 284 OCsH CN CN COOC2H5 -N(CH3)2 blau dunkel- 285 SC6H CN CN COOC2Hs 3NtC2HS)2 blau I 286 SCsH CN CN COOC2HsLN(CH2CH=CH22 blau H3C C2H5 dunkel- 287 SCsH CM CM cOOC2Hs q3 xC2H5 | blau \C2H40COCF /CH2CH=CH2 dunkel- 288 sC2H? CM CN COOC2Hs 3 \C2H4CN blau *) Farbung auf Polyester ßsp. X V VI y2 1 -K Nr. 1 dunkel- 289 SC2H! SC2HICOOC2Hs CN COOC2Ns N C2H4CM blau *) Färbung auf Polyester BeisPiel 290 a) 18,6 Teile 2-Amino-4-chlor-3-cyan-5-formyl-thiophen wurden in 140 Volumenteilen Ethanol suspendiert und mit 2 Teilen Eisessig sowie 2 Teilen Piperidin versetzt. Anschließend ließ man bei Raumtemperatur 50 Volumenteile Cyanessigsäureethylester zutropfen und rührte 7 Stunden bei 60 OC. Der Ansatz wurde in 500 Teile einer Eis/Wassermischung eingerührt, der Niederschlag abgesaugt, mit Wasser gewaschen und bei 60 OC im Vakuum getrocknet. Man erhielt 20 Teile 2-Amino-4-chlor-3-cyan-5-(ßcyan-B-carboethoxy)-vinyl)-thiophen der Formel das ohne weitere Reinigung umgesetzt wird.The dyes listed in the table below were obtained analogously to Examples 155 and 156. E.g. XY y1 y2 -K coloring No. on PES 157 Cl CN COOC2Hs COOC2H5 to, C2H4CN CH3 C2H4CM red- 158 Cl CN COOC2H5 COOCzHs o C2H5 C2H5 blue 159 Cl CN COOC2Hs COOC2H5> N (C2Hs) 2 blue OCH3 160 Cl CN COOC2Hs COOC2Hs <N (C4Hg) 2 blue NHCOCH3 C2H5 161 Cl CN CN CN <, C2H5 blue CH3 C2H5 162 Cl CN COCH3 COOC2H5 <C2H4CN blue CH3 163 Cl COOC2Hs CN COOC2H5 4 - (N (C2HS) 2 blue 0 164 Cl cooc2Hs CM cOOC2Hs 9 N (C2H40CCH3 2 blue CH3 165 Cl COOC2H5 CN COOC2H5 <N {C2Hs) 2 blue NHCOCH3 166 Cl C00C2ll5 COOC2H5 COOC2HS dark 166 C1 COOC2Hs COOC2Hs COOC2Hs dark CH3 Ex. XY t Y2 K -K staining No. on PES C2H5 167 Cl COOC2H5 COCH3 C00C2115 N dark- - C1 COOC2Hs COCH3 COOC2HS C2HoCN blue CH3 168 Cl CooC2Hs COCH3 COCH3 9 C2H4CN blue CH3 C2HS 169 Cl COOC2HS COCH3 CN> oC2H5 dark- C2H 4CN blue C3 0 II C2H4CN 170 Cl C-NH2 CN COOCzHs, dark- CH2CH = CH2 blue CH3 0 171 Cl C-NH2 CN COOC2Hs 9 -N (C2Hs) 2 blue ) = / C2H5 172 Cl so2CH3 CM COOC2Hs 9 oC2H5 dark- C C2H4CN blue CH3 173 Cl S02CH3 CN CQOC2Hs CH2CH = CH22 blue CH3 174 Cl S02CH3 CM COOC2HS N (C2Hs) 2 blue MHCOCH3 ) C / NHCOCH3 175 Cl CN CN COOC2H5 e - =) 2-N (C2H40CCH32 blue C2H4CM 176 Cl CM CM COOC2H5 MI dark CH2CH = CHC blue CH3 Ex. X Y1 y2 -K coloring No. on PCS 177 Cl CN CN COOC2H5 M II dark C2H40CCH3 blue CH3 1 178 Cl CN i CN COOC2Hs 4 N dark- C2H4COO blue cH3 CH3 179 Cl CN CN COOC2H5N (C2HS) 2 dark- - blue C113 180 Cl CM CM COOC2H5 dark M (C4H9> 2 blue CH3 181 Cl CN CM COOC2Hs 9 N (C2Hsl2 blue NHCOCH3 182 Cl CN CN COOC2H5 <SXN (C2Hs 2blue H3C CM 183 Cl CN CN COOC2Hs 4 NHC4Hg blue MHC4H9 184 Cl CN CN COOC2Hs - \) - N (C2Hs) 2 blue MHSO2CH3 185 Cl CN CN COOC2H5 HO-N, N purple ¼ 186 Cl CN CN Cooc2Hs H2N l NN violet CH Ex. XY y2 Y2 -K coloring No. on PES 187 Cl CN CN COOC2HS i / N-CH3 violet C. CsH5 C2H4CN 188 Cl CM CN CONHCH3 ~ <N dark- »== CH2CH = CH2 blue CH3 189 Cl CN CN CONHC2H5> vC2H4CN dark- CH2CH = (blue CH3 C2H4CN 190 Cl CN CN S02CH3 v -41 dark- dark- CN3 191 Cl CN CN COCH3 4 N C2H4CM dark- . »= V CH2CH = CH2 blue CH3 192 Cl CN CN COOCH3>, C2H4CN dark- C CH2CH = CH2 blue CH3 193 Cl CM CM COOC4Hg (n <N (C4Hg} 2 blue NHCOCH3 194 Cl CN CN COOC4H9 (n 9 N (C2H5) 2 blue NHCOCH3 195 Cl CN CN COOC4H9 (n> NHCzH4COC4Hz w blue CH3 CM Cl CN CN COOC4H9 (n) <C2Hs CH3 0 C2H5 197 Cl CN CN CO-NH M dark 8 XC2H4CN blue CIi3 C2H5 198 Cl CN CN N to XC2Hs dark- - - C2H4CM blue CH3 199 Cl CN CN CAN nv c2Hs dark- X \ C2H4CN blue H CH3 / C2Hs 200 Cl CN CN CONH2 <M dark- C) r / XC2H4CN blue CH3 201 Cl CM COOC2Hs COOC2HS <N {C4Hs) 2 marine blue , CH2CH = CH2 202 Cl CN COCH3 COOC2Hs <NsCH2CH = CH2 dark- - C2H4OH blue CH3 , CH2CH = CH2 202 Cl CM CM .CONHCH3> NsCH2CH = CH2 dark- - C2H4OH blue CH3 , C2H5 0 red- 204 Br CN CN COOCzHs to NxC2Hs Ii reddish uC2H40CCH3 blue , C2Hs red- 205 ßr CM CM COOC2Hs o C285 reddish \ C2H4CN blue 206 8r CN CM COOC2Hs zuXCsH40CH3 blue *) Coloring on polyester Ex. XY VI Y2 -K No. dark- 207 Br CN CN coOC2Hs 9 N (C2Hs) 2 blue H3C , C2H4CN dark 208 Br CN CN 'COOC2H5 H> XCH2CH = CH2 blue - CH2CH = CH2 H3C , C2H4OCH3 dark- 209 i Br CN CN COOC2H5 9 XC2H4CN blue C2H4CM 113C 0 - II 0 210 Br CN CM COOC2H5 M (C2H4OCCH3> 2 blue H3C , C2H4CN dark 211 Br CN CN COOC2Hs 4 N blue > C2H401CINHC Hs H3C CH3 4O0 {INHCtH9une1 212 8 rBr CN CN COOC2Hg - HC2H4COOCH blue H3C , C2H dark 213 9r CM CM COOC4Hg (n <blue C2H4OCC2H H3C II 0 214 Br COOC2Hs CN CM a N (C2Hs) 2 blue NHCOCH3 215 Sr COOC2H5 CM COOC2Hg 9 N (CzH40C2Hs blue N (C2H4OC2HS) 2 dark- H3C 0 216 Br COOC2Hs CN CON! CNJ) 2 N (CzH40CCH3 2 blue - purple *) Coloring on polyester w E s RE Ex. XY Y1 Y2 -K No. , C2H4CM dark- 217 / 5r CONH2 CN COOC2Hs <XC2Hs blue H3C iH3C dark 218 Br S02CH3 CN COOC2Hs> oC2H4CN blue H3C I \ oC2H4CN dark 219 Br CON (CH3) 2 CN COOC2H5 9 XC2Hs blue blue H3C CM 0 II dark 220 Br CN CN cooc2Hs U NHC2H40CH3 dUbleal ~ NHC2H40CH3 CH3O 221 Br CN CN COOC2Hs CH30 to blue SN (l 2H5) 2 222 Br CN CN COOCH3 to blue S, N marine- 223 8r CM CN COOCH3 8NHC2HOH blue sC2H4CN dark 224 Cl CN CN 4> \ CHzCH ~ CH2 blue H3C 225 F CN CN dark 225 F CM CM COOC2H5 blue dark- 226 F CN CN COOC2Hs to N (CH2CH = CH2 2 blue *) Coloring on polyester | -: E.g. XY y1 Y2 -K *) No. - 22? F CM CM C00C2H5 CO, CN2CH = CH2 dark- J \ C2HGCN , CH2CH = CH2 dark- 228 F COOC2H5 CN COOC2Hs t3 blue blao oC2H4CN dark 229 OC2H CM coOC2Hs COOC2HS a XCzHs blue > - LBXS H3C 230 OC2H5 CN COOC2Hs ClJoc2Hs z XC2H4CN dark- 231 OC2HT CN COOC2Hs COOC2H5 83N (C2H5) 2 blue I OCHs 232 OC2H CM cOOCzHs COOCzHs NHCOCH3 blue NHCOCH3 , C2Hs dark 233 CM CN CN CN 83 XC2Ht, CN blue In blue H3C , C2Hs dark 234 C2 CM COCH3 COOC2Hs 9 XC2H4CN blue OC2H C2H4CM NHCOCH3 235 CM COOC2H5 & i (C2HS> 2 blue 235 OC2HS (COOC2Hs CN COOC2HS C2Hg) 2 blue 236 CM COOC2H5 (C2ll4OCCll32 blue 236 0C2H | COOC2Hs CN ) Y blue 237-0C2HslcOOc2Hs CN 1C00C2H5 NNCOCH3 ll NHCOCH3 *) Coloring on polyester Ex. XY Y2 -K No. C2H5 COOC2H5 COOC2H5 COOC2Hs / C2HJ dark- 238 OC2HlCOOC2H5 COOC2Hs cOOC2Hs $ 3 XC2H4CN blue H3C . XC2H5 dark 239 OC2F1 | COOCZH5 COCH3 COOC2Hs H3C XC2H4CN blue \ C2H4CN 240 OC2HlCOOC2H5 COCH3 COCH3 COCH3 »C2Hs violet H3C , C2H5 OC2H (COOC2H5 COCH3 CN / C2H5 dark- 241 OC2HICOOC2Hs COCH3 CM <XC2HCN blue \ C2HGCN 242 OC2HT C-MH2 CN COOC2Hs H3C N / C2H4CN blue H3C 243 OC2H C-NH2 CN COOC2Hs 43N (C2Hs} 2 blue NHCOCH3 , C2H5 dark 244 OC2H S02CH3 CN COOC2Hs <XC2HxCN blue OC2H H3C H3C 245 0C2Hg; S02CH3 CM COOC2Hs vN (CH2CH = CH2 2 blue H3C 246 SO2CH3 CM COOC2Hs M (C2Hs> 2 blue - | NHCOCH3 / C2H5 reddish NHCOCH3 24 7 OC2HT CN CN CON (CH3} 2 <XC2H4CN -N blue j 248 OC2H5 CM CM COOC2Hs -N (C2H40CCH3) 2 blue *) Coloring on polyester Ex. XY VI Y2 -K ww No. / C2HCN dark OCH CzHiCN dark- 249 OC2H 'CN CN COOC2H5 w blue \ CH2CH = CHC, H3C / C2Hs 0 dark 250 OC2H J CN CN COOC2Hs <t) -N 1 blue C2H4OCCH3 , C2Hs dark 251 OC2H CN CN COOCzH5> blue XC2H4COOCH H3C 252 oC2H CM CM COOC2Hs g (C2H5) 2 dUnbl ul- H3C dark- 253 OC2H; CN CN COOC2HsN (C4Hs) 2 blue OC2H H3C blue 254 oc2 CN CN COOC2Hs 8 3 N (C2Hs) 2 MHCOCH3 blue 255 OC2H CN CN COOC2Hs <S 1 N {C2H5) H3C CM 256 OC2H CN CN COOC2H5 WHC4H9 blue NHC4Hg 257 OC2H CN CN COOC4Hs (n 9 N (C4Hg) 2 blue NHCOCH3 258 OC2H CN CN COOC4Hg (n 9 N (C2H5> 2 blue l | | NHCOCH3 l *) Coloring on polyester E.g. XY V1 Y2 -K *) No. 259 OC2H, CN CN COOC4Hgfn 33N (C2H4COOC41 19 blue H3C , C2Hs dark 260 OC2H; CN CN COOC4H9 (n <»N blue -C2H4COC2H 0C2H5 H3C 0 mx / c2Hs dark 281 OC2H CM CN CoNH4>\>4> 9N blue H3C , C2H5 dark 262 OC2H CM CM t3 aN blue H3C 263 OC2H CN CN dark SN OC2H CM CM CMI N XC2H4CN blue H H3C n / c2Hs dark- 264 OC2H CM CM CONH2 \ N \ C2H4CN blue 2 "\ C2H4CN H3C marine- 265 OC2H; CN COOC2Hs COOC2Hs t3N (C4Hg) 2 blue t , CH2CH = CH2 \ CH2CH = CH2 / CH2CH = CH2 dark- 265 OC2H CN COCH3 COOC2Hs <> \ »N blue H3C / CH2CH = CH2 dark- 267 OC2 CN CN CONHCH3 nN blue H3C marine- 268 OC2H; CN CN COOC2Hs - vN (C2Hs) 2 blue l NHS02CH3 *) Coloring on polyester Ex. X | Y y1 y2 -K t) No. 269 OC2H CN CN COOC2Hs HO <violet ¼ E. 270 OCzH CN CN Cooc2Hs N <violet I. 271 OC2H CN CN COOC2HS violet tCSCH3 blue 272 Z CM C2H4CN N / CN24c11Cc2 dark O & 2H CM H3C H? C 273 OC2H5 CM CM 'COMHC2HS XCzH4CN dark- OC2H - blue DISC H3C 274 Of2H CM CM SO2CH3 / C2H6CN blue 27; OC2H - CN CH2CH = CH2 H3C -s sCzH4CN dark- 275 OCH CM CM COCH3 9 XCH2CH = CH2 blue OC2HJ H3C, C2H4CN dark- 276 OC2H5 CN CN COOCH3 / C2H4CN dark- I H3C 271 OCH3 CN OOCZHSC2Hg 0 277 OCH3 CN CN COOC2Hs o SC2Hs II blue- C2H4OCCH3 purple *) Coloring on polyester 278 OC6H CN CN cooc2Hs T XC2H4CN purple , C2H5 279 SC6H CN CM COOC2HS C2Hs blue- 4 XC2H40CH3 purple dark- 280 SC6H CN CN COOC2Hs vN (C2Hs) 2 blue H3C / C2H4CN dark- 281 OCH3 CM CM COOC2Hs 83 XCH2CH = CH2 blue H3C CH3 0 282 OCH3 CM CM COOC2H5 H $ ½ \ N HC2H4COO blue H3C 283 OCH3 CM CM COOC4Hg (n 83 xC2Hs blue H3C I) 0 dark- 284 OCsH CN CN COOC2H5 -N (CH3) 2 blue dark- 285 SC6H CN CN COOC2Hs 3NtC2HS) 2 blue I. 286 SCsH CN CN COOC2HsLN (CH2CH = CH22 blue H3C C2H5 dark 287 SCsH CM CM COOC2Hs q3 xC2H5 | blue \ C2H40COCF / CH2CH = CH2 dark- 288 sC2H? CM CN COOC2Hs 3 \ C2H4CN blue *) Color on polyester ßsp. XV VI y2 1 -K No. 1 dark 289 SC2H! SC2HICOOC2Hs CN COOC2Ns N C2H4CM blue *) Coloring on polyester Example 290 a) 18.6 parts of 2-amino-4-chloro-3-cyano-5-formylthiophene were suspended in 140 parts by volume of ethanol, and 2 parts of glacial acetic acid and 2 parts of piperidine were added. Then 50 parts by volume of ethyl cyanoacetate were added dropwise at room temperature and the mixture was stirred at 60 ° C. for 7 hours. The batch was stirred into 500 parts of an ice / water mixture, the precipitate was filtered off with suction, washed with water and dried at 60 ° C. in vacuo. 20 parts of 2-amino-4-chloro-3-cyano-5- (β-cyan-B-carboethoxy) vinyl) thiophene of the formula were obtained which is implemented without further purification.

b) 14 Teile 2-Amino-4-chlor-3-cyan-5-(ß-cyan-ß-carboethoxy)-vinyl)-thiophen wurden in 100 Volumenteilen Phosphorsäure 85 % suspendiert und bei 0 - 5 OC langsam mit 16 Teilen Nitrosylschwefelsäure (11,5 % N203) versetzt. Nach 2 h bei 0 - 5 OC ließ man die Diazoniumsalzlösung in eine Lösung von 9,75 Teilen N-Cyanethyl-N-ethyl-m-toluidin in einer Mischung aus 125 Teilen Wasser, 500 Teilen Eis, 25 Volumenteilen 32 %iger Salzsäure und 1 Teil Amidosulfonsäure einfließen. Nach Beendigung der Kupplung wurde der Farbstoff abgesaugt, neutral gewaschen und im Vakuum getrocknet. Man erhielt 20 Teile des in Beispiel 155 beschriebenen Farbstoffs der Formel der auf Polyester dunkelblaue Färbungen mit allgemein guten Echtheiten ergibt.b) 14 parts of 2-amino-4-chloro-3-cyano-5- (ß-cyano-ß-carboethoxy) vinyl) thiophene were suspended in 100 parts by volume of 85% phosphoric acid and slowly added 16 parts at 0-5 ° C Nitrosylsulfuric acid (11.5% N203) added. After 2 h at 0-5 ° C., the diazonium salt solution was left in a solution of 9.75 parts of N-cyanoethyl-N-ethyl-m-toluidine in a mixture of 125 parts of water, 500 parts of ice, 25 parts by volume of 32% strength hydrochloric acid and Pour in 1 part sulfamic acid. After the coupling had ended, the dye was filtered off with suction, washed neutral and dried in vacuo. 20 parts of the dye of the formula described in Example 155 were obtained which gives dark blue dyeings with generally good fastness properties on polyester.

BeisPiel 291 14,5 Teile 2-Amino-3-cyan-4-ethoxy-5-( (ß-cyan-ß-carboethoxy)-vinyl)-thiophen wurden in 160 Volumenteilen Phosphorsäure 85 % suspendiert und bei 0-5 °C mit 16 Teilen Nitrosylschwefelsäure (11,5 % N203) diazotiert. Nach 2 h bei 0-5 OC setzt man die Diazoniumsalzlösung analog Beispiel 290 mit 9,75 Teilen N-Cyanethyl-N-ethyl-m-toluidin zu 20 Teilen des Farbstoffs der Formel um, mit dem auf Polyester blaue Färbungen mit guter Licht- und Thermofixierechtheit erhalten wurden.Example 291 14.5 parts of 2-amino-3-cyano-4-ethoxy-5- ((ß-cyano-ß-carboethoxy) vinyl) thiophene were suspended in 160 parts by volume of 85% phosphoric acid and at 0-5 ° C diazotized with 16 parts of nitrosylsulfuric acid (11.5% N203). After 2 hours at 0-5 ° C., the diazonium salt solution is added analogously to Example 290 with 9.75 parts of N-cyanoethyl-N-ethyl-m-toluidine to 20 parts of the dye of the formula um, with which blue dyeings with good lightfastness and heat-setting fastness were obtained on polyester.

Beispiel 292 14 Teile 2-Amino-4-cnlor-3-cyan-5-((ß-cyan-ß-methylaminocarbonyl)-vìnyl)-thiophen wurden in 120 Volumenteilen Phosphorsäure 85 % suspendiert, bei 0-5 OC mit 16 Teilen Nitrosylschwefelsäure umgesetzt und 2 h bei 0-5 OC gerührt. Die Diazoniumsalzlösung ließ man in eine Mischung aus 7,5 Teilen N,N-Diethylanilin, 100 Teilen Wasser1 300 Teilen Eis, 25 Volumenteilen 32 %iger Salzsäure und 1 Teil Amidosulfonsäure langsam einfließen. Nach beendeter Kupplung wurde die Suspension filtriert, neutral gewaschen und getrocknet. Man erhielt 16 Teile des Farbstoffs der Formel der auf Polyester dunkelblaue Färbungen mit allgemein guten Echtheiten ergibt.Example 292 14 parts of 2-amino-4-chloro-3-cyano-5 - ((β-cyano-β-methylaminocarbonyl) -vìnyl) -thiophene were suspended in 120 parts by volume of phosphoric acid 85%, at 0-5 ° C. with 16 parts Nitrosylsulfuric acid reacted and stirred at 0-5 ° C. for 2 h. The diazonium salt solution was allowed to slowly flow into a mixture of 7.5 parts of N, N-diethylaniline, 100 parts of water, 300 parts of ice, 25 parts by volume of 32% hydrochloric acid and 1 part of sulfamic acid. After the coupling had ended, the suspension was filtered, washed neutral and dried. 16 parts of the dye of the formula were obtained which gives dark blue dyeings with generally good fastness properties on polyester.

Analog den Beispielen 290 - 292 wurden auch die in der nachfolgenden Tabelle gekennzeichneten Verbindungen erhalten. asp. x Y Y1 Y2 -K Nr. dunkel- 293 Br CN CN COOCH3 3N(C2Hs}2 diaukel- 0 II dunkel- 294 8r CN CN COOCH:? t C2H40CCH 3 3 blau 295 8r CN CN COOCH3 83N(C2Hs}2 blau NHCOCH3 296 Br CN CN COOCH3 {¼1SM(CH> N baublau N(C2H5)i! 25f dunkel- 297 Cl CM CM COOC2H5 N<CH2CH=CH2>2 blau dunkel- 298 Cl CN CN COOC2H5 vN(4H9)2 blau H3C ,C2H4CN dunkel- 299 Cl CN CN COOC2Hs\CH2CH=CH2/ blau CH2CH=CH2 300 Cl CN CN COOC2H5 XN dunkel- 1SM(C2H5>2 blau x) Färbung auf Polyester NrP- X r y1 t2 K *} , \ dunkel- 301 Cl CN CN CONHCH3 <~»NlC2Hs)2 blau dunkel- 302 Cl COOCH3 CN CoOC2Hs t3N(C2Hs)2 blau ,C2H5 dunkel- 303 Cl SO2CH3 CN COOC2HS wN blau ll3C H3C CN rotstichig 304 Cl CN CN COOC2H5 aNHC2H40CH3 blau NHC2H40CH3 ,CH2CH=CH2 dunkel- 305 F CN CN COOC2Hs 9 XC2H4CN blau H3C dunkel- 306 F CN CN COOC2Hs t3N(C4Hg) 2 blau 307 F CN CN COOC2Hs 83N(C2H5)2 blau OCH3 308 Cl CN I CN CN t3N(C2H5)2 blau dunkel- 309 °C2 CN CN COOCH3 t3N (CzHs) 2 blau 310 OC2H CM CM COOCH3 - N(C2Hs)2 blau NHCOCH3 dunkel- 311 OCH3 CM CM jCOOC2Hs M(CH2CH=CH2>2 blau *) Färbung auf Polyester Bsp. X Y y1 y2 -K * } Nr. ,-> dunkel- 312 OC2H CN CN COOC2Hs NIC4Hg}2 blau H3C ,C2H4CM dunkel- 313 SC6H CN CN COOC2H5 9 N- blau XCH2CH=CH2 dunkel- 314 OC2 CN CN COOCH3(C2Hs)2 blau ,CH2CH=CH2 dunkel- 315 SC6H CN CN cOOC2HS ~<« F N blau \C2HCN H3C *) Färbung auf PolyesterThe compounds identified in the table below were also obtained analogously to Examples 290-292. asp. x Y Y1 Y2 -K No. dark- 293 Br CN CN COOCH3 3N (C2Hs} 2 dial- 0 II dark 294 8r CN CN COOCH :? t C2H40CCH 3 3 blue 295 8r CN CN COOCH3 83N (C2Hs} 2 blue NHCOCH3 296 Br CN CN COOCH3 {¼1SM (CH> N blue N (C2H5) i! 25f dark 297 Cl CM CM COOC2H5 N <CH2CH = CH2> 2 blue dark- 298 Cl CN CN COOC2H5 vN (4H9) 2 blue H3C , C2H4CN dark 299 Cl CN CN COOC2Hs \ CH2CH = CH2 / blue CH2CH = CH2 300 Cl CN CN COOC2H5 XN dark 1SM (C2H5> 2 blue x) coloring on polyester NrP- X r y1 t2 K *} , \ dark- 301 Cl CN CN CONHCH3 <~ »NlC2Hs) 2 blue dark- 302 Cl COOCH3 CN CoOC2Hs t3N (C2Hs) 2 blue , C2H5 dark 303 Cl SO2CH3 CN COOC2HS wN blue ll3C H3C CN reddish 304 Cl CN CN COOC2H5 aNHC2H40CH3 blue NHC2H40CH3 , CH2CH = CH2 dark- 305 F CN CN COOC2Hs 9 XC2H4CN blue H3C dark- 306 F CN CN COOC2Hs t3N (C4Hg) 2 blue 307 F CN CN COOC2Hs 83N (C2H5) 2 blue OCH3 308 Cl CN I CN CN t3N (C2H5) 2 blue dark- 309 ° C2 CN CN COOCH3 t3N (CzHs) 2 blue 310 OC2H CM CM COOCH3 - N (C2Hs) 2 blue NHCOCH3 dark- 311 OCH3 CM CM jCOOC2Hs M (CH2CH = CH2> 2 blue *) Coloring on polyester Ex. XY y1 y2 -K *} No. , -> dark- 312 OC2H CN CN COOC2Hs NIC4Hg} 2 blue H3C , C2H4CM dark- 313 SC6H CN CN COOC2H5 9 N- blue XCH2CH = CH2 dark- 314 OC2 CN CN COOCH3 (C2Hs) 2 blue , CH2CH = CH2 dark- 315 SC6H CN CN cOOC2HS ~ <«FN blue \ C2HCN H3C *) Coloring on polyester

Claims

Patent claims 1. Compounds of the general formula I in which X is fluorine, chlorine, bromine or optionally substituted hydroxy or mercapto, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, carbon ester or optionally substituted carbamoyl, T hydrogen, C1- to C4-alkyl, an introducible by electrophilic substitution A radical or a radical of the formula -CH = T1, where T1 is the radical of a methylene-active compound and K is the radical of a coupling component.

2. Compounds according to claim 1, in which K is a radical of the general formulas in which R1 is hydrogen, alkyl, aralkyl or aryl, R2 is hydrogen or R3 (R3 is optionally substituted alkyl, cycloalkyl, alkenyl, aralkyl or aryl, R4 and Rs are independently hydrogen, alkyl, alkoxy, phenoxy, halogen, alkylsulfonylamino, dialkylaminosulfonylamino or Acylamino, R6 are cyano, carbamoyl, nitro or carbalkoxy and R7 are optionally substituted phenyl, alkyl, aralkyl, halogen, substituted hydroxy or mercapto.

Compounds according to claim 1 of the formulas in which Xr chlorine, bromine, optionally substituted hydroxy or mercapto, y2 cyano, carbon ester or substituted carbamoyl, T2 formyl, nitro, cyano, Z2 cyano, carbon ester or substituted carbamoyl and K1 the remainder of a coupling component of the aniline, thiazole, pyrazole , Thiophene or pyridine series.

Use of the compounds according to Claim 1 for dyeing synthetic Polyester.