DE2739842A1 - Di:cyano mono:azo dyes - used for dyeing polyester(s) in fast red to violet shades - Google Patents

Di:cyano mono:azo dyes - used for dyeing polyester(s) in fast red to violet shades

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Publication number
DE2739842A1
DE2739842A1 DE19772739842 DE2739842A DE2739842A1 DE 2739842 A1 DE2739842 A1 DE 2739842A1 DE 19772739842 DE19772739842 DE 19772739842 DE 2739842 A DE2739842 A DE 2739842A DE 2739842 A1 DE2739842 A1 DE 2739842A1
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Germany
Prior art keywords
alkyl
hydrogen
halogen
alkenyl
radicals
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.)
Granted
Application number
DE19772739842
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German (de)
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DE2739842C2 (en
Inventor
Rainer Dr Hamprecht
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Bayer AG
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Bayer AG
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Filing date
Publication date
Priority to DE19772739842 priority Critical patent/DE2739842A1/en
Application filed by Bayer AG filed Critical Bayer AG
Priority to JP53027838A priority patent/JPS6027695B2/en
Priority to GB09821/78A priority patent/GB1559562A/en
Priority to CH272278A priority patent/CH645232GA3/de
Priority to IT21186/78A priority patent/IT1093708B/en
Priority to BR7801540A priority patent/BR7801540A/en
Priority to ES467845A priority patent/ES467845A1/en
Priority to FR7807285A priority patent/FR2383924A1/en
Publication of DE2739842A1 publication Critical patent/DE2739842A1/en
Priority to US06/449,310 priority patent/US4452609A/en
Priority to US06/470,080 priority patent/US4479899A/en
Application granted granted Critical
Publication of DE2739842C2 publication Critical patent/DE2739842C2/de
Granted legal-status Critical Current

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Classifications

    • 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
    • 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
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines

Abstract

New azo cpds. are of formula (I). In (I), R1 is (ar)alkyl, alkenyl or (hetero)aryl; R2 is H or alkyl; R3 is H, alkyl, a halogen, CN, OR' or C COOR'; R4 is H, (ar)alkyl, aryl or cycloalkyl, R5 is H (ar)alkyl or alkenyl; Y is CN, halogen, CF3, NO2 or SO2R1; Y1 is halogen or CN. X1 is H or a substit. having a para equiv. of -0.3 to +0.3 (Hammet); X2 is H, halogen, or OR1, COOR1, COOH, NR2CHO, CF3, NR2COR1; N(COR1)2, NR2SO2R1 or NR2SO2N(R2)2, X3 is alkyl or X2; and X1 forms with X2 and X3 the gp.- and R4, as well as R4 and R5, can be joined by an alkenyl chain, the alkyl, aralkyl, alkenyl, aryl and heteroaryl residues mentioned here alone optionally carrying non-ionic or COOH substs. Red to violet colourants for spin dying and mass colouring synthetic textiles such as polyamides and partic. polyesters such as polyethylene terephthalate. They can also be used for cellulose acetates, cellulose triacetate, polyurethanes, polyolefines and hydrocarbons.

Description

AzoverbindungenAzo compounds

Gegenstand der Erfindung sind Azoverbindungen der Formel worin R1 Alkyl, Alkenyl, Aralkyl, Aryl oder Hetaryl, R2 Wasserstoff oder Alkyl, R3 Wasserstoff, Alkyl, Halogen, Cyan, OR1 oder COOR1 R4 Wasserstoff, Alkyl, Aralkyl, Aryl oder Cycloalkyl, R5 Wasserstoff, Alkyl, Alkenyl oder Aralkyl Y Chlor, Brom oder Jod, X1 Wasserstoff oder ein Substituent mit einem Hammet'schen #-para-Wert von -0,3 bis +0,3 X2 Wasserstoff, Alkyl, Halogen, OR1, COOR1, COOH, NR2CHO, CF3, NR2COR1, N(COR1)2 NR2SO2R1 oder NR2S02(R2)2' X3 Alkyl oder X2 und X1 mit X2 oder X3 die Gruppierung -OCH2OCH2- sind, und R3 und R4, sowie R4 und R5 durch eine Alkylenkette verbunden sein können, wobei die vorstehend genannten Alkyl-, Aralkyl-, Alkenyl-, Aryl und Hetarvlreste gegebenenfalls durch nichtionische Substituenten oder COOH substituiert sind.The invention relates to azo compounds of the formula wherein R1 is alkyl, alkenyl, aralkyl, aryl or hetaryl, R2 is hydrogen or alkyl, R3 is hydrogen, alkyl, halogen, cyano, OR1 or COOR1, R4 is hydrogen, alkyl, aralkyl, aryl or cycloalkyl, R5 is hydrogen, alkyl, alkenyl or aralkyl Y is chlorine , Bromine or iodine, X1 hydrogen or a substituent with a Hammet's #para value of -0.3 to +0.3 X2 hydrogen, alkyl, halogen, OR1, COOR1, COOH, NR2CHO, CF3, NR2COR1, N (COR1) 2 NR2SO2R1 or NR2S02 (R2) 2 'X3 alkyl or X2 and X1 with X2 or X3 are the grouping -OCH2OCH2-, and R3 and R4, as well as R4 and R5 can be connected by an alkylene chain, the above-mentioned alkyl, aralkyl- , Alkenyl, Aryl and Hetarvlreste are optionally substituted by nonionic substituents or COOH.

Geeignete Substituenten X1 mit einem Hammet'schen cSpara-Wert von -0,3 bis +0,3 sind solche, wie sie in H.A. Staab "Einführung in die theoretische organische Chemie", Verlag Chemie, Weinheim/Bergstraße 1970, aufgeführt sind bzw. sind in der Farbstoffchemie übliche, schwach elektronenabgebende oder schwach elektronenanziehende bevorzugt nichtionische Substituenten und Wasserstoff. Beispielsweise seien genannt: Alkyl, Aryl, Aralkyl, O-Alkyl, O-Aryl, O-Aralkyl, Halogen, -NR2COR1, -N(COR1)2, -NR2CHO, und -NR2S02R1, wobei Alkyl bevorzugt ist.Suitable substituents X1 with a Hammet cSpara value of -0.3 to +0.3 are those as listed in HA Staab "Introduction to Theoretical Organic Chemistry", Verlag Chemie, Weinheim / Bergstrasse 1970, or Weak electron-donating or weakly electron-withdrawing, preferably nonionic substituents and hydrogen, are customary in dye chemistry. Examples include: alkyl, aryl, aralkyl, O-alkyl, O-aryl, O-aralkyl, halogen, -NR2COR1, -N (COR1) 2, -NR2CHO, and -NR2SO2R1, with alkyl being preferred.

Die Alkylenketten welche R3 und R4 bzw. R4 und R5 verbinden können, weisen vorzugsweise 3 bis 5 C-Atome auf.The alkylene chains which R3 and R4 or R4 and R5 can connect, preferably have 3 to 5 carbon atoms.

Bevorzugte Verbindungen sind solche der Formel I, worin X1 Alkyl, X2 Wasserstoff, Wasserstoff, Alkyl oder -O-Alkyl Y Brom und Chlor R1 Alkyl, R2 Wasserstoff R3 Wasserstoff R4 Wasserstoff, Aralkyl, Alkyl oder Cycloalkyl R5 Alkenyl oder R4 bedeuten, wobei die vorstehend im beliebigen Zusammenhang genannten Alkylreste vorzugsweise 1-4 C-Atome aufweisen und vorzugsweise einfach durch Halogen, -CN, COOH oder Aryl oder eine Gruppe (-OCH2CH2)nOR1 (n = 1-8) substituiert sein können, die Alkenylreste vorzugsweise 3-5 C-Atome aufweisen und gegebenenfalls durch Halogen substituiert sein können, die Aralkylreste vorzugsweise Benzyl und Phenyläthylreste sind, die vorzugsweise 1-3-mal durch Alkyl, O-Alkyl, Halogen und Nitro substituiert sein können, die Arylreste vorzugsweise Phenylreste sind, die vorzugsweise 1-3-mal durch Alkyl, O-Alkyl, Halogen, -CN, N02 oder -C00-C1-C4-Alkyl substituiert sein können, die Hetarylreste vorzugsweise Pyridin-, Chinolin-oder Thiophenreste sind, und unter Halogen vorzugsweise Brom und Chlor zu verstehen ist.Preferred compounds are those of the formula I in which X1 is alkyl, X2 is hydrogen, hydrogen, alkyl or -O-alkyl, Y is bromine and chlorine, R1 is alkyl, R2 is hydrogen, R3 is hydrogen, R4 is hydrogen, aralkyl, alkyl or cycloalkyl, R5 is alkenyl or R4, where the alkyl radicals mentioned above in any context preferably have 1-4 carbon atoms and preferably simply by halogen, -CN, COOH or aryl or a group (-OCH2CH2) nOR1 (n = 1-8) can be substituted, the alkenyl radicals preferably have 3-5 carbon atoms and can optionally be substituted by halogen, the aralkyl radicals are preferably benzyl and phenylethyl radicals, which are preferably 1 -3 times can be substituted by alkyl, O-alkyl, halogen and nitro, the aryl radicals are preferably phenyl radicals, which are preferably 1-3 times by alkyl, O-alkyl, halogen, -CN, NO2 or -C00-C1- C4-alkyl can be substituted, the hetaryl radicals are preferably pyridine, quinoline or thiophene radicals, and halogen is preferably to be understood as meaning bromine and chlorine.

Bevorzugte Alkylreste sind Methyl, Äthyl, n-Propyl und n-Butyl.Preferred alkyl radicals are methyl, ethyl, n-propyl and n-butyl.

Bevorzugter Arylrest ist Phenyl, "sperrige" Reste (z.B.The preferred aryl group is phenyl, "bulky" groups (e.g.

t-Butyl) befinden sich vorzugsweise in solchen Positionen, wo sie keine sterische Hinderung bewirken (z.B. in m- oder vorzugsweise p-Stellung eines Phenylrestes).t-Butyl) are preferably in those positions where they do not cause steric hindrance (e.g. in the m- or preferably p-position of a Phenyl radicals).

Cycloalkyl ist vorzugsweise Cyclohexyl.Cycloalkyl is preferably cyclohexyl.

Ganz besonders bevorzugt sind Verbindungen der Formel I, worin X2, X3, R2 und R3 Wasserstoff x1 C1-C4-Alkyl, Y Brom R1 C1-C4-Alkyl R4 Wasserstoff, C1-C4-Alkyl, das durch C1-C4-Alkoxy substituiert sein kann, R5 Benzyl, Phenäthyl, C1-C4-Alkyl, das durch C1-C4-Alkoxy substituiert sein kann, bedeuten.Compounds of the formula I in which X2, X3, R2 and R3 hydrogen x1 C1-C4-alkyl, Y bromine R1 C1-C4-alkyl R4 hydrogen, C1-C4-alkyl, which can be substituted by C1-C4-alkoxy, R5 benzyl, phenethyl, C1-C4-alkyl, which can be substituted by C1-C4-alkoxy, mean.

Die Herstellung der neuen Verbindungen der Formel (I) erfolgt in an sich bekannter Weise z.B. durch Kupplung diazotierter Aniline der Formel (II) auf Kupplungskomponenten der Formel (III) worin X1-X3 Y, R1 -R5 die vorbeschriebene Bedeutung haben.The new compounds of the formula (I) are prepared in a manner known per se, for example by coupling diazotized anilines of the formula (II) on coupling components of the formula (III) wherein X1-X3 Y, R1 -R5 have the meaning described above.

Die erfindungsgemäßen Verbindungen eignen sich zuB PãrteMh~ von synthetischen Textilmaterialien, insbesondere Textilmaterialien aus sekundärem Celluloseacetat und Cellulosetriacetat, Polyamid, wie z.B. Polyhexamethylenadipamid, und ganz besonders aromatischem Polyester, wie z.B. Polyäthylenterephthalat nach den für diese Faserarten üblichen Färbemethoden unter Verwendung wäßriger oder nicht wäßriger Flotten eingesetzt werden.The compounds according to the invention are suitable for the preparation of synthetic products Textile materials, in particular textile materials made from secondary cellulose acetate and cellulose triacetate, polyamide such as polyhexamethylene adipamide, and most particularly aromatic polyester such as polyethylene terephthalate according to the type of fiber used for these types of fibers customary dyeing methods using aqueous or non-aqueous liquors are used will.

Darüber hinaus sind die neuen Verbindungen Ausgangsmaterialien zur Herstellung wertvoller bekannter o-Cyanazofarbstoffe, wie wie z.B. in DT-PS 1 544 563 (US-PS 3 962 209) beschrieben sind.In addition, the new compounds are starting materials for Production of valuable known o-cyanazo dyes, such as in DT-PS 1 544 563 (U.S. Patent 3,962,209).

Beispiel 1 Herstellung der Farbstoffe der Formel Eine Lösung von 26,5 g 2.6-Dibrom-4-methyl-anilin in 125 ml 60 %iger Schwefelsäure wird bei 38-400C mit 17 ml einer 42 %igen Nitrosylschwefelsäure diazotiert. Man rührt noch 60 Minuten bei 400 und fügt dann die Lösung der Diazokomponente bei 0-5 0C zu einer Lösung bzw. Suspension von 24,2 g 3-Diäthylamino-methansulfonanilid und 2 g Amidosulfonsäure in 200 ml Wasser. Durch Zufügen von Natriumacetat wird der pH-Wert auf 3 gehoben. Man saugt ab und wäscht mehrmals mit Wasser.Example 1 Preparation of the dyes of the formula A solution of 26.5 g of 2,6-dibromo-4-methyl-aniline in 125 ml of 60% strength sulfuric acid is diazotized at 38-400 ° C. with 17 ml of a 42% strength nitrosylsulfuric acid. The mixture is stirred for a further 60 minutes at 400 and then the solution of the diazo component is added at 0-5 ° C. to a solution or suspension of 24.2 g of 3-diethylamino-methanesulphonanilide and 2 g of amidosulphonic acid in 200 ml of water. The pH is raised to 3 by adding sodium acetate. It is suctioned off and washed several times with water.

Ausbeute: 45,5 g Der Farbstoff färbt Polyesterfasern in oranger Nuance mit guten allgemeinen Echtheiten, insbesondere Licht-, Sublimier- und Naßechtheiten.Yield: 45.5 g. The dye dyes polyester fibers in an orange shade with good general fastness properties, in particular light, sublimation and wet fastness properties.

Bei analoger oder ähnlicher Arbeitsweise erhält man die in nachfolgender Tabelle angegebenen Farbstoffe. Beispiel Formel Farbton auf Nr. Polyester 2 CH3-/ NHS02CH3 orange NHS02CH3 r 3 H3C < -N=N 2 N(C4 orange r 4 CH3'\-N=NN(C2H40C4H9) orange r NHS02CH3 Cl 5 CH3 4 -N=N 9 -N(C2H4°c3H7)2 orange NHS02CH3 ßr 6 CH3 < -N=N 9 -N(CH2CH=CH2)2 orange NHS0 2CH3 If the procedure is analogous or similar, the dyes given in the table below are obtained. Example formula hue on No. polyester 2 CH3- / NHS02CH3 orange NHS02CH3 r 3 H3C <-N = N 2 N (C4 orange r 4 CH3 '\ - N = NN (C2H40C4H9) orange r NHS02CH3 Cl 5 CH3 4 -N = N 9 -N (C2H4 ° c3H7) 2 orange NHS02CH3 ßr 6 CH3 <-N = N 9 -N (CH2CH = CH2) 2 orange NHS0 2CH3

Claims (6)

Patentansprüche 1. Azoverbindungen der Formel worin R1 Alkyl, Alkenyl, Aralkyl, Aryl oder Hetaryl, R2 Wasserstoff oder Alkyl, R3 Wasserstoff, Alkyl, Halogen, Cyan, ORl oder COOR1 R4 Wasserstoff, Alkyl, Aralkyl, Aryl oder Cycloalkyl, R5 Wasserstoff, Alkyl, Alkenyl oder Aralkyl Y Chlor, Brom oder Jod, xl Wasserstoff oder ein Substituent mit einem Hammet'schen #-para-Wert von -0,3 bis +0,3 X2 Wasserstoff, Alkyl, Halogen, OR1, COOR1, COOH, NR2CHO, CF3, NR2COR1, N(COR1)2 NR2SO2R1 oder NR2S02(R2)2, X3 Alkyl oder X2 und X1 mit X2 oder X3 die Gruppierung -OCH20CH2- sind, und R3 und R4, sowie R4 und Rj durch eine Alkylenkette verbunden sein können, wobei die vorstehend genannten Alkyl-, Aralkyl-, Alkenyl-, Ary und Hetarylreste gegebenenfalls durch nichtionische Substituenten oder COOH substituiert sind.Claims 1. Azo compounds of the formula wherein R1 is alkyl, alkenyl, aralkyl, aryl or hetaryl, R2 is hydrogen or alkyl, R3 is hydrogen, alkyl, halogen, cyano, ORl or COOR1, R4 is hydrogen, alkyl, aralkyl, aryl or cycloalkyl, R5 is hydrogen, alkyl, alkenyl or aralkyl Y is chlorine , Bromine or iodine, xl hydrogen or a substituent with a Hammet's #para value of -0.3 to +0.3 X2 hydrogen, alkyl, halogen, OR1, COOR1, COOH, NR2CHO, CF3, NR2COR1, N (COR1) 2 NR2SO2R1 or NR2S02 (R2) 2, X3 alkyl or X2 and X1 with X2 or X3 are the grouping -OCH20CH2-, and R3 and R4, as well as R4 and Rj can be connected by an alkylene chain, the aforementioned alkyl, aralkyl- , Alkenyl, ary and hetaryl radicals are optionally substituted by nonionic substituents or COOH. 2. Azoverbindungen gemäß Anspruch 1, worin X1 Alkyl, X2 Wasserstoff, X3 Wasserstoff, Alkyl oder -O-Alkyl, Y Brom und Chlor, R1 Alkyl, R2 Wasserstoff, R3 Wasserstoff, Rd Wasserstoff, Aralkyl, Alkyl oder Cycloalkyl, R5 Alkenyl oder R4 bedeuten, wobei die vorstehend im beliebigen Zusammenhang genannten Alkylreste 1-4 C-Atome aufweisen und einfach durch Halogen, oder Aryl oder eine Gruppe (-OCH2CH2)nOR1 (n = 1-8) substituiert sein können, die Alkenylreste 3-5 C-Atome aufweisen und gegebenenfalls durch Halogen substituiert sein können, die Aralkylreste Benzyl und Phenylätherreste sind, die 1-3-mal durch Alkyl, O-Alkyl, Halogen und Nitro substituiert sein können, die Arylreste Phenylreste sind, die 1-3-mal durch Alkyl, O-Alkyl, Halogen, -NC, N02 oder -COO-C1-C4-Alkyl substituiert sein können, die Heterylreste Pyridin-, Chinolin- oder Thiophenreste sind, und unter Halogen Brom und Chlor zu verstehen ist.2. Azo compounds according to claim 1, wherein X1 is alkyl, X2 is hydrogen, X3 is hydrogen, alkyl or -O-alkyl, Y is bromine and chlorine, R1 is alkyl, R2 is hydrogen, R3 is hydrogen, Rd is hydrogen, aralkyl, alkyl or cycloalkyl, R5 is alkenyl or R4, where the alkyl radicals mentioned above in any context have 1-4 carbon atoms and are simply replaced by halogen, or aryl or a group (-OCH2CH2) nOR1 (n = 1-8) can be substituted, the alkenyl radicals have 3-5 carbon atoms and can optionally be substituted by halogen, the aralkyl radicals are benzyl and phenyl ether radicals, the 1-3- times can be substituted by alkyl, O-alkyl, halogen and nitro, the aryl radicals are phenyl radicals which are substituted 1-3 times by alkyl, O-alkyl, halogen, -NC, NO2 or -COO-C1-C4-alkyl can, the heteryl radicals are pyridine, quinoline or thiophene, and halogen is to be understood as bromine and chlorine. 3. Azoverbindungen gemäß Anspruch 1, worin X2, X3, R2 und R3 Wasserstoff X1 C1-C4-Alkyl, Y Brom R1 C1-C4-Alkyl R4 Wasserstoff, C1-C4-Alkyl, das durch C1-C4-Alkoxy substituiert sein kann, R5 Benzyl, Phenäthyl, C1-C4-Alkyl das durch C1-C4-Alkoxy substituiert sein kann, bedeuten.3. Azo compounds according to claim 1, wherein X2, X3, R2 and R3 are hydrogen X1 C1-C4-alkyl, Y bromine R1 C1-C4-alkyl R4 hydrogen, C1-C4-alkyl, replaced by C1-C4-alkoxy can be substituted, R5 benzyl, phenethyl, C1-C4-alkyl that by C1-C4-alkoxy may be substituted, mean. 4. Azoverbindung gemäß Anspruch 1 der Formel 4. Azo compound according to claim 1 of the formula 5. Verfahren zur Herstellung von Azoverbindungen gemäß Anspruch 1, dadurch gekennzeichnet, daB man diazotierte Aniline der Formel worin X1 - X3 und Y die in Anspruch 1 genannte Bedeutung haben, mit Kupplungskomponenten der Formel, in der R1-R5 die in Anspruch 1 genannte Bedeutung haben, vereinigt.5. Process for the preparation of azo compounds according to Claim 1, characterized in that diazotized anilines of the formula are used wherein X1 - X3 and Y have the meaning given in claim 1, with coupling components of the formula in which R1-R5 have the meaning given in claim 1, combined. 6. Verfahren zum Färben und/oder Bedrucken von Fasermaterialien, dadurch gekennzeichnet, daß man Azofarbstoffe gemäß Anspruch 1 verwendet.6. A method for dyeing and / or printing fiber materials, thereby characterized in that azo dyes according to Claim 1 are used.
DE19772739842 1977-03-15 1977-09-03 Di:cyano mono:azo dyes - used for dyeing polyester(s) in fast red to violet shades Granted DE2739842A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE19772739842 DE2739842A1 (en) 1977-09-03 1977-09-03 Di:cyano mono:azo dyes - used for dyeing polyester(s) in fast red to violet shades
GB09821/78A GB1559562A (en) 1977-03-15 1978-03-13 Azo compounds
CH272278A CH645232GA3 (en) 1977-03-15 1978-03-13
IT21186/78A IT1093708B (en) 1977-03-15 1978-03-13 AZOIC COMPOUNDS
JP53027838A JPS6027695B2 (en) 1977-03-15 1978-03-13 Azo compound
BR7801540A BR7801540A (en) 1977-03-15 1978-03-14 AZOCOMPOSTOS, PROCESS FOR ITS PREPARATION AND APPLICATION
ES467845A ES467845A1 (en) 1977-03-15 1978-03-14 Dyeing red with 2,6-dicyano-2'-sulfonamido-4'-amino-azo-benzenes
FR7807285A FR2383924A1 (en) 1977-03-15 1978-03-14 NEW AZOIC COMPOUNDS, THEIR PREPARATION PROCESS AND THEIR TINCTORIAL APPLICATIONS
US06/449,310 US4452609A (en) 1977-03-15 1982-12-13 Dyeing red with 2,6-dicyano-2'-sulfonamido-4'-amino-azo-benzenes
US06/470,080 US4479899A (en) 1977-03-15 1983-03-01 Red dyeing 2,6-dicyano-2'-sulfonamido-4'-amino-azo-benzenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19772739842 DE2739842A1 (en) 1977-09-03 1977-09-03 Di:cyano mono:azo dyes - used for dyeing polyester(s) in fast red to violet shades

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DE2739842A1 true DE2739842A1 (en) 1979-03-15
DE2739842C2 DE2739842C2 (en) 1987-02-05

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2004131A1 (en) * 1970-01-30 1971-08-05 Bayer Ag Monoazo dyes
DE2318294A1 (en) * 1972-04-12 1973-10-25 Nippon Kayaku Kk AZO COMPOUNDS, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE FOR THE COLORING OF TEXTILE GOODS

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2004131A1 (en) * 1970-01-30 1971-08-05 Bayer Ag Monoazo dyes
DE2318294A1 (en) * 1972-04-12 1973-10-25 Nippon Kayaku Kk AZO COMPOUNDS, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE FOR THE COLORING OF TEXTILE GOODS

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