DE1266421B - Process for the preparation of water-insoluble monoazo dyes - Google Patents

Process for the preparation of water-insoluble monoazo dyes

Info

Publication number
DE1266421B
DE1266421B DEF32117A DEF0032117A DE1266421B DE 1266421 B DE1266421 B DE 1266421B DE F32117 A DEF32117 A DE F32117A DE F0032117 A DEF0032117 A DE F0032117A DE 1266421 B DE1266421 B DE 1266421B
Authority
DE
Germany
Prior art keywords
water
hydrogen
cyananiline
chloro
och
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.)
Pending
Application number
DEF32117A
Other languages
German (de)
Inventor
Dr Winfried Kruckenberg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF32117A priority Critical patent/DE1266421B/en
Priority to CH958961A priority patent/CH405548A/en
Priority to GB3071661A priority patent/GB933160A/en
Priority to BE607974A priority patent/BE607974A/en
Publication of DE1266421B publication Critical patent/DE1266421B/en
Pending legal-status Critical Current

Links

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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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

Landscapes

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

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.:Int. Cl .:

C09bC09b

Deutsche Kl.: 22a-lGerman class: 22a-l

Nummer: 1266421Number: 1266421

Aktenzeichen: F 32117IV c/22 aFile number: F 32117IV c / 22 a

Anmeldetag: 14. September 1960Filing date: September 14, 1960

Auslegetag: 18. April 1968Open date: April 18, 1968

Es wurde gefunden, daß man wertvolle wasserunlösliche Monoazofarbstoffe erhält, wenn mäh die Diazoverbindung eines der folgenden Amine 4-Nitro-2-cyananilin, 2,4-, 3,4- oder 2,5-Dicyananilin, 3-Chlor-4-cyananilin, 2-Cyan-5-chloranilin, 2-Chlor-4-cyananilin, 2,4-Dicyan-6-chloranilin, 2-Cyan-o-brom-4-nitranilin mit einem Amin der allgemeinen FormelIt has been found that valuable water-insoluble monoazo dyes are obtained if the Diazo compound one of the following amines 4-nitro-2-cyananiline, 2,4-, 3,4- or 2,5-dicyananiline, 3-chloro-4-cyananiline, 2-cyano-5-chloroaniline, 2-chloro-4-cyanoaniline, 2,4-dicyano-6-chloroaniline, 2-cyano-o-bromo-4-nitroaniline with an amine of the general formula

CH2CH2OCH2CH2COOZCH 2 CH 2 OCH 2 CH 2 COOZ

in p-Stellung zur Aminogruppe kuppelt. In der . allgemeinen Formel bedeutet der Substituent X Wasserstoff, eine Alkyl- oder Alkoxygruppe, Y Wasserstoff oder eine Alkoxygruppe, R steht für Wasserstoff, Alkyl, Cyanalkyl oder eine Gruppierungcouples in the p-position to the amino group. In the . In general formula, the substituent X denotes hydrogen, an alkyl or alkoxy group, Y Hydrogen or an alkoxy group, R represents hydrogen, alkyl, cyanoalkyl or a group

— CH2CH2OCH2CH2COOz- CH 2 CH 2 OCH 2 CH 2 COOz

und Z für einen niederen Alkylrest.and Z is a lower alkyl radical.

Die Kupplung der Ausgangskomponenten erfolgt in üblicher Weise in vorzugsweise saurer Lösung oder Suspension.The starting components are coupled in the customary manner, preferably in an acidic solution or suspension.

Als Kupplungskomponenten der Formel I können z. B. Verwendung finden: N,N-Di-(carboxymethyläthoxy-äthyl)-anilin, N,N-Di-(carboxymethyl-äthoxy-äthyl)-m-toluidin, N,N-Di-(carboxymethyl-äthoxy-äthyl)-kresidin, N,N-Di-(carboxymethyl-äthoxyäthyl) - aminohydrochinon - dimethyläther, N - Äthyl-N - (carboxymethyl - äthoxy - äthyl) - anilin, N - Cyanäthyl - N - (carboxymethyl - äthoxy - äthyl) - anilin, N-iCarboxymethyl-äthoxy-äthylJ-N^carboxymethyläthoxy-äthyl)-m-toluidin, N-(carboxymethyl-äthoxyäthyl)-N-(carboxymethyl-äthoxy-äthyl)-kresidin. As coupling components of the formula I, for. B. Use: N, N-Di- (carboxymethylethoxy-ethyl) -aniline, N, N-Di- (carboxymethyl-ethoxy-ethyl) -m-toluidine, N, N-Di- (carboxymethyl-ethoxy-ethyl) -cresidine, N, N-Di- (carboxymethyl-ethoxyethyl) - aminohydroquinone - dimethyl ether, N - ethyl-N - (carboxymethyl - ethoxy - ethyl) - aniline, N - cyanoethyl - N - (carboxymethyl - ethoxy - ethyl) - aniline, N-iCarboxymethyl-ethoxy-ethylJ-N ^ carboxymethylethoxy-ethyl) -m-toluidine, N- (carboxymethyl-ethoxyethyl) -N- (carboxymethyl-ethoxy-ethyl) -cresidine.

Gegenüber den aus der britischen Patentschrift 593 567 bekannten nächstvergleichbaren Farbstoffen zeigen die verfahrensgemäß erhältlichen Farbstoffe den Vorteil der besseren Sublimierechtheit der Färbung auf Polyäthylenterephthalat.Compared to the closest comparable dyes known from British patent specification 593 567 the dyes obtainable according to the process show the advantage of better fastness to sublimation Coloring on polyethylene terephthalate.

Beispielexample

14,3 Gewichtsteile l-Amino-2,4-dicyanbenzol werden in 400 Gewichtsteilen konzentrierter Schwefelsäure bei 0 bis 150C gelöst und mit 170 Gewichtsteilen Nitrosylschwefelsäure (42 g Nitrit in 100 ml H2SO4) unter gutem Rühren und Kühlen diazotiert und nach etwa 3 Stunden auf etwa 3000 Gewichtsteile Eis Verfahren zur Herstellung wasserunlöslicher
Monoazofarbstoffe14.3 parts by weight of l-amino-2,4-dicyanobenzene are dissolved in 400 parts by weight of concentrated sulfuric acid at 0 to 15 0 C and (2 SO 4 42 g nitrite in 100 ml H) diazotized with 170 parts by weight nitrosylsulfuric acid under good agitation and cooling, and after about 3 hours on about 3000 parts by weight of ice process for the preparation of water-insoluble
Monoazo dyes

AnmeldenRegister

Farbenfabriken Bayer Aktiengesellschaft,
5090 LeverkusenPaint factories Bayer Aktiengesellschaft,
5090 Leverkusen

Als Erfinder benannt:Named as inventor:

Dr. Winfried Kruckenberg, 5090 LeverkusenDr. Winfried Kruckenberg, 5090 Leverkusen

gegossen. Ein geringer Nitritüberschuß wird mit Amidosulfonsäure entfernt und die Lösung filtriert. Diese Lösung wird dann mit einer Lösung von 35,3 Gewichtsteilen N,N-Di-(carboxymethyl-äthoxyäthyl)-anilin der Formelpoured. A small excess of nitrite is removed with sulfamic acid and the solution is filtered. This solution is then mixed with a solution of 35.3 parts by weight of N, N-di- (carboxymethyl-ethoxyethyl) -aniline the formula

/CH2CH2- 0-CH2CH2-COOCH3
^CH7CH2- O - CH7CH,- COOCH3 / CH 2 CH 2 - O-CH 2 CH 2 -COOCH 3
^ CH 7 CH 2 - O - CH 7 CH, - COOCH 3

vereinigt, mit verdünnter Natronlauge teilweise neutralisiert und die Kupplung mit Natriumacetat zu Ende geführt. Der Farbstoff wird filtriert und gewaschen. Es bildet in trockenem Zustand ein schwarzrotes Pulver, das sich in organischen Lösungsmitteln, wie Aceton oder Alkohol, mit roter Farbe löst. Acetatseide- und Polyamidgewebe färbt es, durch geeignete Zusätze in feine Verteilung gebracht, in klaren blaustichigroten Tönen von guter Wasch- und Lichtechtheit an.combined, partially neutralized with dilute sodium hydroxide solution and the coupling with sodium acetate brought to the end. The dye is filtered and washed. It forms a when dry Black-red powder that turns red in organic solvents, such as acetone or alcohol solves. It dyes acetate silk and polyamide fabrics, finely divided by suitable additives, in clear blue-tinged red tones with good wash and lightfastness.

In gleicher Weise erhält man Farbstoffe, mit denen sich auf Polyäthylenterephthalatgewebe orange Färbungen erhalten lassen, wenn man als Kupplungskomponente 27,6 Gewichtsteile N-Cyanäthyl-N-carboxymethyl-äthoxy-äthyl-anilin oder 25,1 Gewichtsteile N-Äthyl-N-carboxymethylräthoxy-äthyl-anilin verwendet.In the same way, dyes are obtained with which the polyethylene terephthalate fabric turns orange Dyeings can be obtained if 27.6 parts by weight of N-cyanoethyl-N-carboxymethyl-ethoxy-ethyl-aniline are used as the coupling component or 25.1 parts by weight of N-ethyl-N-carboxymethylratshoxy-ethyl-aniline used.

Nach dem Verfahren dieses Beispiels erhält man bei Verwendung der entsprechenden Ausgangskomponenten gleichfalls die in der folgenden TabelleFollowing the procedure of this example, using the appropriate starting components, one obtains likewise those in the following table

3 43 4

angegebenen Farbstoife, die Polyäthylenterephthalatfasern in den angegebenen Tönen farben.specified dyes, the polyethylene terephthalate fibers in the specified tones colors.

O7NO 7 N

O,N 0>NO, N 0> N

N(CH2CH2OCH2CH2COOCH3)2 N (CH 2 CH 2 OCH 2 CH 2 COOCH 3 ) 2

N(CH2CH2OCH2CH2COOCH3)2 N (CH 2 CH 2 OCH 2 CH 2 COOCH 3 ) 2

N(CH2CH2OCH2CH2COOCH3)2 /CH2CH2CNN (CH 2 CH 2 OCH 2 CH 2 COOCH 3 ) 2 / CH 2 CH 2 CN

CH2CH2OCH2CH2COOCh3 CH2CH2CNCH 2 CH 2 OCH 2 CH 2 COOCh 3 CH 2 CH 2 CN

^CH2Ch2OCH2CH2COOCH3 ^ CH 2 Ch 2 OCH 2 CH 2 COOCH 3

CH2CH2CN
CH2CH2OCH2CH2COOCh3 CH 2 CH 2 CN
CH 2 CH 2 OCH 2 CH 2 COOCh 3

CH2CH2CN
CH2CH2OCH2CH2COOCh3 CH 2 CH 2 CN
CH 2 CH 2 OCH 2 CH 2 COOCh 3

Blaustichiges RotBluish red

Orangeorange

Orangeorange

BordoBordo

Gelbstichiges OrangeYellowish orange

Blaustichiges RotBluish red

Gelbstichiges RotYellowish red

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von wasserunlös- worin Y Wasserstoff oder eine Alkoxygruppe,Process for the production of water-insoluble in which Y is hydrogen or an alkoxy group, liehen Monoazofarbstoffe^ dadurch ge- X Wasserstoff, eine Alkyl- oder Alkoxygruppe,borrowed monoazo dyes ^ thereby being X hydrogen, an alkyl or alkoxy group, kennzeichnet, daß man die Diazover- R Wasserstoff, Alkyl, Cyanalkyl oder eine Grup^indicates that the diazo R is hydrogen, alkyl, cyanoalkyl or a group ^ bindung eines der folgenden Amine 4-Nitro- 45 pierung
2-cyananilin, 2,4-, 3,4- oder 2,5-Dicyananilin,binding of one of the following amines 4-nitro- 45 pation
2-cyananiline, 2,4-, 3,4- or 2,5-dicyananiline, 3-Chlor-4-cyananilin, 2-Cyan-5-chlor-anilin, — CHOCH2OCH2CH2COOZ3-chloro-4-cyananiline, 2-cyano-5-chloro-aniline, - CHOCH2OCH2CH2COOZ 2-Chlor-4-cyananilin, 2,4-Dicyan-6-chloranilin,2-chloro-4-cyananiline, 2,4-dicyan-6-chloroaniline, 2-Cyan-6-brom-4-nitranilin mit Aminen der all- bedeutet und Z einen niederen Alkylrest darstellt,2-cyano-6-bromo-4-nitroaniline with amines which means all and Z is a lower alkyl radical, gemeinen Formel 50 in p-Stellung zur Aminogruppe kuppelt.common formula 50 in the p-position to the amino group. CH2CH2OCH2CH2COOzCH 2 CH 2 OCH 2 CH 2 COOz In Betracht gezogene Druckschriften: Britische Patentschrift Nf. 593 567; USA.-Patentschrift Nr. 2 373 700.Documents considered: British Patent Nf. 593 567; U.S. Patent No. 2,373,700.
DEF32117A 1960-09-14 1960-09-14 Process for the preparation of water-insoluble monoazo dyes Pending DE1266421B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DEF32117A DE1266421B (en) 1960-09-14 1960-09-14 Process for the preparation of water-insoluble monoazo dyes
CH958961A CH405548A (en) 1960-09-14 1961-08-16 Process for the preparation of water-insoluble monoazo dyes
GB3071661A GB933160A (en) 1960-09-14 1961-08-25 Water-insoluble monoazo dyestuffs
BE607974A BE607974A (en) 1960-09-14 1961-09-08 Water insoluble monoazo dyes, their production process and application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF32117A DE1266421B (en) 1960-09-14 1960-09-14 Process for the preparation of water-insoluble monoazo dyes

Publications (1)

Publication Number Publication Date
DE1266421B true DE1266421B (en) 1968-04-18

Family

ID=7094498

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF32117A Pending DE1266421B (en) 1960-09-14 1960-09-14 Process for the preparation of water-insoluble monoazo dyes

Country Status (4)

Country Link
BE (1) BE607974A (en)
CH (1) CH405548A (en)
DE (1) DE1266421B (en)
GB (1) GB933160A (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2373700A (en) * 1940-06-29 1945-04-17 Eastman Kodak Co Azo compounds and material colored therewith
GB593567A (en) * 1940-07-10 1947-10-21 American Cyanamid Co Azo dyes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2373700A (en) * 1940-06-29 1945-04-17 Eastman Kodak Co Azo compounds and material colored therewith
GB593567A (en) * 1940-07-10 1947-10-21 American Cyanamid Co Azo dyes

Also Published As

Publication number Publication date
BE607974A (en) 1962-01-02
GB933160A (en) 1963-08-08
CH405548A (en) 1966-01-15

Similar Documents

Publication Publication Date Title
DE1220061B (en) Process for the production of water-insoluble azo dyes
DE1544375B1 (en) Water-insoluble monoazo dyes
DE2833854C2 (en) New navy blue disperse dyes, processes for their production and their use for dyeing or printing synthetic fiber materials
DE1940685C3 (en) Disperse dyes of the amino pyrazole series, process for their manufacture and use
DE1644150A1 (en) Water-insoluble azo dyes and process for their preparation and use
DE1282815B (en) Process for the preparation of water-insoluble monoazo dyes
DE1644052A1 (en) Process for the production of new, water-insoluble azo dyes
DE1544421A1 (en) Process for the preparation of water-insoluble monoazo dyes
DE1266421B (en) Process for the preparation of water-insoluble monoazo dyes
DE2612790C2 (en) Disperse monoazo dyes, their production and use
DE2623251A1 (en) DISPERSE MONOAZO DYES
DE2831675A1 (en) BENZISOTHIAZOLAZO DYES
DE942221C (en) Process for the preparation of water-insoluble monoazo dyes
DE2010491C3 (en) Azo dyes soluble in water and their use
DE692648C (en) Process for the production of azo dyes
DE1108355B (en) Process for the preparation of water-insoluble azo dyes
DE1217007B (en) Process for the production of dyes
DE1231364B (en) Process for the preparation of water-insoluble azo dyes
DE1644122C3 (en) Water-insoluble monoazo dyes free from sulfonic acid and carboxylic acid groups and process for their preparation
DE1544391C (en) Process for the preparation of water-insoluble monoazo dyes
DE1768979C (en) Water-insoluble p-aminoazo dyes
DE2137023C (en) Monoazo dyes, process for their preparation and their use
DE600544C (en) Process for the preparation of monoazo dyes
AT227852B (en) Process for the preparation of new water-insoluble monoazo dyes
DE1221746B (en) Process for the preparation of water-insoluble monoazo dyes