DE1276843B - Process for the production of water-insoluble azo dyes - Google Patents

Process for the production of water-insoluble azo dyes

Info

Publication number
DE1276843B
DE1276843B DEF37563A DEF0037563A DE1276843B DE 1276843 B DE1276843 B DE 1276843B DE F37563 A DEF37563 A DE F37563A DE F0037563 A DEF0037563 A DE F0037563A DE 1276843 B DE1276843 B DE 1276843B
Authority
DE
Germany
Prior art keywords
water
production
azo dyes
insoluble azo
ococh
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
DEF37563A
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 DEF37563A priority Critical patent/DE1276843B/en
Priority to DEF39347A priority patent/DE1220061B/en
Priority to CH939264A priority patent/CH467840A/en
Priority to CH747966A priority patent/CH453288A/en
Priority to CH896663A priority patent/CH436213A/en
Priority to US299692A priority patent/US3268507A/en
Priority to AT638863A priority patent/AT251137B/en
Priority to DK382263AA priority patent/DK109458C/en
Priority to GB31559/63A priority patent/GB1024485A/en
Priority to NO149689A priority patent/NO121798B/no
Publication of DE1276843B publication Critical patent/DE1276843B/en
Priority to NL7106458A priority patent/NL7106458A/xx
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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
    • D06P1/08—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal cationic azo dyes

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.:Int. Cl .:

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

C09bC09b

Deutsche KL: 22 a -1German KL: 22 a -1

P 12 76 843.3-43 (F 37563)P 12 76 843.3-43 (F 37563)

10. August 1962August 10, 1962

5. September 19685th September 1968

Es wurde gefunden, daß man wertvolle wasserunlösliche Azofarbstoffe erhält, wenn man die Diazoverbindung eines der folgenden Cyananiline: 2,4-, 2,5- oder 3,4-Dicyananilin, 3-Chlor-4-cyananilin, 2-Cyan-5-chloranilin, 2-Chlor-4-cyananilin, 2-Cyan-4,5,6-trichloranilin oder 2,4-Dicyan-6-chloranilin mit einem Amin der allgemeinen FormelIt has been found that valuable water-insoluble azo dyes are obtained if the diazo compound is used one of the following cyananilines: 2,4-, 2,5- or 3,4-dicyananiline, 3-chloro-4-cyananiline, 2-cyano-5-chloroaniline, 2-chloro-4-cyanoaniline, 2-cyano-4,5,6-trichloroaniline or 2,4-dicyan-6-chloroaniline with an amine of the general formula

Verfahren zur Herstellung von wasserunlöslichen AzofarbstoffenProcess for the production of water-insoluble azo dyes

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,

5090 Leverkusen5090 Leverkusen

Als Erfinder benannt:Named as inventor:

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

worin X Wasserstoff, Alkyl, Alkoxy oder Halogen und Ri eine Gruppe gruppe kuppelt und dabei die Ausgangskomponenten frei von Sulfonsäure- und Carbonsäuregruppenwherein X is hydrogen, alkyl, alkoxy or halogen and Ri is a group group and the starting components are free of sulfonic acid and carboxylic acid groups

wählt.
Die Kupplung der Ausgangskomponenten erfolgtchooses.
The coupling of the starting components takes place

in üblicher Weise in vorzugsweise saurer Lösung bedeutet, wobei R3 einen niederen Alkylrest darstellt, 20 oder Suspension, und worin R2 für Cyanalkyl, /i-Carboalkoxyäthyl oder für einen Rest Ri steht, in p-Stellung zur Amino-in the usual way in preferably acidic solution, where R3 is a lower alkyl radical, 20 or suspension, and where R 2 is cyanoalkyl, / i-carboalkoxyethyl or a radical Ri, in the p-position to the amino

— CH2CH2 — OCOR:!
O- CH 2 CH 2 - OCOR :!
O

Als Kupplungskomponente können z. B. die Amine mit nachstehenden Formeln Verwendung finden:As a coupling component, for. B. the amines with the following formulas are used:

-C2H4CN-C 2 H 4 CN / \ / \ /C2H4COOCH3 / C 2 H 4 COOCH 3 — Ν- Ν ^C2H4OCOCH3
0^ C 2 H 4 OCOCH 3
0 CH3 CH 3 OO C2H4OCOC2H5
0C 2 H 4 OCOC 2 H 5
0 /C2H4OCOCH3
— Ν/ C 2 H 4 OCOCH 3
- Ν O
Μ O
Μ OO ^C2H4OCOCH3 ^ C 2 H 4 OCOCH 3 C2H4OCOCH3 C 2 H 4 OCOCH 3 IlIl
οο C2H4OCOCH3 C 2 H 4 OCOCH 3 00

Die verfahrensgemäß erhältlichen Farbstoffe eignen sich vorzüglich zum Färben und Bedrucken hydrophober Materialien, wie Textilien oder Fasern aus aromatischen Polyestern, ζ. B. von Polyäthylenterephthalaten oder von Kondensationsprodukten aus Terephthalsäure und l,4-(bis-Hydroxymethyl)-benzol. Man erhält auf diesen Materialien Färbungen und Drucke mit sehr guten Echtheitseigenschaften, insbesondere sehr guter Licht-, Wasch-, und Sublimierechtheit. The dyes obtainable according to the process are eminently suitable for dyeing and printing more hydrophobic Materials such as textiles or fibers made from aromatic polyesters, ζ. B. of polyethylene terephthalates or of condensation products from terephthalic acid and 1,4- (bis-hydroxymethyl) benzene. Dyes and prints with very good fastness properties are obtained on these materials, especially very good fastness to light, washing and sublimation.

Die Farbstoffe eignen sich auch zum Färben und Bedrucken von Celluloseacetat und Triacetylcellulose und von Polyamid- und Polyacrylnitrilfasermaterial. Die Farbstoffe zeichnen sich ferner durch gute Kristallisationsfähigkeit und gutes Ziehvermögen aus.The dyes are also suitable for dyeing and printing cellulose acetate and triacetyl cellulose and of polyamide and polyacrylonitrile fiber material. The dyes are also characterized by good quality Crystallizability and good drawability.

Gegenüber dem in der USA.-Patentschrift 2 249 749 (fünftletzte Diazokomponente der Tabelle auf S. 5 in Kombination mit der Kupplungskomponente Nr. 8 der Tabelle auf S. 4) beschriebenen Farbstoff zeigt der erfindungsgemäß erhältliche Farbstoff derCompared to that in US Pat. No. 2,249,749 (fifth from last diazo component in the table on p. 5 in combination with the coupling component no. 8 of the table on page 4) described dye shows the dye obtainable according to the invention

809 599/493809 599/493

V- N = N -/"V- N = N - / "

Formelformula

den Vorteil der besseren Lichtechtheit der Färbungen auf Superpolyamidgewebe.the advantage of the better lightfastness of the dyeings on super polyamide fabrics.

Beispielexample

N(CH2CH2OCOOC2Hs)2 N (CH 2 CH 2 OCOOC 2 Hs) 2

schwefelsäure (42 g Nitrit in 100 ml H2SO4) unter gutem Rühren und Kühlen diazotiert und nach etwa 3 Stunden auf etwa 3000 Gewichtsteile Eis gegossen. Ein geringer Nitritüberschuß wird mit Amidosulfon-sulfuric acid (42 g nitrite in 100 ml H2SO4) with thorough stirring and cooling diazotized and after about Poured onto about 3000 parts by weight of ice for 3 hours. A small excess of nitrite is used with amidosulfone

14,4 Gewichtsteile 2,4-Dicyananilin werden in 10 säure entfernt und die Lösung filtriert. Diese Lösung 400 Gewichtsteilen konzentrierter Schwefelsäure bei wird dann mit einer Lösung von 29,7 Gewichtsteilen 0 bis 15° C gelöst und mit 170 Volumteilen Nitrosyl- der Aminoverbindung der Formel14.4 parts by weight of 2,4-dicyananiline are removed in 10 acid and the solution is filtered. This solution 400 parts by weight of concentrated sulfuric acid at is then with a solution of 29.7 parts by weight 0 to 15 ° C and with 170 parts by volume of nitrosyl the amino compound of the formula

IlIl

C2H4OCOCH3
C2H4OCOCH3 C 2 H 4 OCOCH 3
C 2 H 4 OCOCH 3

Il οIl ο

gebracht, in klaren orangeroten Tönen von guter Wasch- und Lichtechtheit.brought, in clear orange-red tones of good wash and lightfastness.

Auf gleichem Wege lassen sich aus den. entsprechenden Ausgangskomponenten die nachfolgenden Farbstoffe erhalten, die Gewebe aus aromatischen Polyestern, wie Polyäthylenterephthalaten, in den angegebenen Farbtönen färben:In the same way, the. corresponding starting components the following Dyes obtained, the fabrics made of aromatic polyesters, such as polyethylene terephthalates, in the specified Coloring shades:

vereinigt,' mit verdünnter Natronlauge teilweise neutralisiert und die Kupplung mit Natnumacetat zu Ende geführt. Der Farbstoff wird filtriert und gewaschen. Es bildet sich in trockenem Zustand ein orangerotes Pulver, das sich in organischen Lösungsmitteln, wie Aceton oder Alkohol, mit orangeroter Farbe löst. Acetatseide und Polyamidgewebe färbt es, durch geeignete Zusätze in feine Verteilungcombined, '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 when dry Orange-red powder that dissolves in organic solvents, such as acetone or alcohol, with orange-red Color dissolves. It dyes acetate silk and polyamide fabric, finely dispersed with suitable additives

CNCN

XC2H4COOCH3 XC 2 H 4 COOCH 3

N OrangeN orange

^C2H4OCOCH3 ^ C 2 H 4 OCOCH 3

/C2H4COOCH3 / C 2 H 4 COOCH 3

N gelbstichiges OrangeN yellowish orange

^C2H4OCOCH3 ^ C 2 H 4 OCOCH 3

/C2H4CN/ C 2 H 4 CN

C2H4OCOCH3 O stark gelbstichiges OrangeC 2 H 4 OCOCH 3 O strongly yellowish orange

NCNC

NCNC

NZC2H4OCOCH3^ rotstichiges OrangeNZC 2 H 4 OCOCH 3 ^ reddish orange

Il I O J2 Il IO J 2

NfC2H4OCOCH3^ O ι NfC 2 H 4 OCOCH 3 ^ O ι

RotRed

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung wasserunlöslicher Azofarbstoffe, dadurch gekennzeichnet, daß man die Diazoverbindung eines der folgenden Cyananiline: 2,4-, 2,5- oder 3,4-Dicyananilin, 3-Chlor-4-cyananilin, 2-Cyan-5-chloranilin, 2-Chlor-4-cyananilin, 2-Cyan-4,5,6-trichloranilin, 2,4-Dicyan-6-chloranilin mit einem Amin der allgemeinen FormelProcess for the production of water-insoluble azo dyes, characterized in that that the diazo compound is one of the following cyananilines: 2,4-, 2,5- or 3,4-dicyananiline, 3-chloro-4-cyananiline, 2-cyano-5-chloroaniline, 2-chloro-4-cyananiline, 2-cyano-4,5,6-trichloroaniline, 2,4-Dicyan-6-chloroaniline with an amine of the general formula /R2 / R 2 IOIO worin X Wasserstoff, Alkyl, Alkoxy oder Halogen und Ri eine Gruppewherein X is hydrogen, alkyl, alkoxy or halogen and Ri is a group — CH2CH2 — OCOR3 - CH 2 CH 2 - OCOR 3 bedeutet, wobei R3 einen niederen Alkylrest darstellt, und worin R2 für Cyanalkyl, /5-Carboalkoxyäthyl oder für einen Rest Ri steht, in p-Stellung zur Aminogmppe kuppelt und· dabei die Ausgangskomponenten frei von Sulfonsäure- und Carbonsäuregruppen wählt.where R3 is a lower alkyl radical, and where R 2 is cyanoalkyl, / 5-carboalkoxyethyl or a radical Ri, couples in the p-position to the amino group and · thereby selects the starting components free of sulfonic acid and carboxylic acid groups. In Betracht gezogene Druckschriften: 15 USA.-Patentschrift Nr. 2 249 749.References considered: 15 U.S. Patent No. 2,249,749. Bei der Bekanntmachung der Anmeldung ist eine Färbetafel mit Erläuterungen ausgelegt worden.When the application was announced, a coloring table with explanations was laid out. 809 599/493 8.68 Q Bundesdruckerei Berlin809 599/493 8.68 Q Bundesdruckerei Berlin
DEF37563A 1962-08-10 1962-08-10 Process for the production of water-insoluble azo dyes Pending DE1276843B (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
DEF37563A DE1276843B (en) 1962-08-10 1962-08-10 Process for the production of water-insoluble azo dyes
DEF39347A DE1220061B (en) 1962-08-10 1963-03-28 Process for the production of water-insoluble azo dyes
CH939264A CH467840A (en) 1962-08-10 1963-07-18 Process for the preparation of water-insoluble azo dyes
CH747966A CH453288A (en) 1962-08-10 1963-07-18 Process for dyeing and printing hydrophobic textile fibers with azo dyes
CH896663A CH436213A (en) 1962-08-10 1963-07-18 Process for dyeing and printing hydrophobic textile fibers
US299692A US3268507A (en) 1962-08-10 1963-08-01 Water-insoluble monoazo dyestuffs
AT638863A AT251137B (en) 1962-08-10 1963-08-08 Process for the production of new, water-insoluble azo dyes
DK382263AA DK109458C (en) 1962-08-10 1963-08-09 Process for the preparation of water-insoluble, sulfonic acid and carboxylic acid group-free monoazo dyes.
GB31559/63A GB1024485A (en) 1962-08-10 1963-08-09 Water-insoluble azo dyestuffs
NO149689A NO121798B (en) 1962-08-10 1963-08-09
NL7106458A NL7106458A (en) 1962-08-10 1971-05-11

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF37563A DE1276843B (en) 1962-08-10 1962-08-10 Process for the production of water-insoluble azo dyes

Publications (1)

Publication Number Publication Date
DE1276843B true DE1276843B (en) 1968-09-05

Family

ID=7096942

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF37563A Pending DE1276843B (en) 1962-08-10 1962-08-10 Process for the production of water-insoluble azo dyes

Country Status (1)

Country Link
DE (1) DE1276843B (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2249749A (en) * 1939-11-14 1941-07-22 Eastman Kodak Co Azo compounds and material colored therewith

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2249749A (en) * 1939-11-14 1941-07-22 Eastman Kodak Co Azo compounds and material colored therewith

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