DE533795C - Process for the preparation of water-insoluble azo dyes - Google Patents

Process for the preparation of water-insoluble azo dyes

Info

Publication number
DE533795C
DE533795C DEJ35450D DEJ0035450D DE533795C DE 533795 C DE533795 C DE 533795C DE J35450 D DEJ35450 D DE J35450D DE J0035450 D DEJ0035450 D DE J0035450D DE 533795 C DE533795 C DE 533795C
Authority
DE
Germany
Prior art keywords
preparation
water
azo dyes
insoluble azo
dyes
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.)
Expired
Application number
DEJ35450D
Other languages
German (de)
Inventor
Dr Leopold Laska
Dr Arthur Zitscher
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEJ35450D priority Critical patent/DE533795C/en
Application granted granted Critical
Publication of DE533795C publication Critical patent/DE533795C/en
Expired 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
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films

Landscapes

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

Description

Verfahren zur Darstellung von wasserunlöslichen Azofarbstoffen Es wurde gefunden, daß man zu wertvollen, wasserunlöslichen Azofarbstoffen gelangt, wenn man Diazo-, Tetrazo- oder Diazoazoverbindungen, welche keine Sulfon- oder Carbonsäuregruppe enthalten, mit 2, 3-Oxviiaphthoyl-4-aminoacenaphthen kuppelt.Process for the preparation of water-insoluble azo dyes Es it was found that valuable, water-insoluble azo dyes can be obtained, if you have diazo, tetrazo or diazoazo compounds which do not have a sulfonic or carboxylic acid group contained, coupled with 2, 3-Oxviiaphthoyl-4-aminoacenaphthen.

Die neuen Farbstoffe können zur Herstellung echter Färbungen und Drucke auf der Faser Verwendung finden oder auch zur Bereitung wertvoller Pigmente.The new dyes can be used to produce real dyeings and prints can be used on the fiber or for the preparation of valuable pigments.

Bei Verwendung von :2, 3-0-xynaphthoyl-.4-aminoacenaphthen, welches bisher zur Herstellung von Azofarbstoffen noch nicht herangezogen worden ist, werden überraschenderweise gegenüber dem bekannten 2, 3-OXY-iiaphthoyl-i-naphthylamin die Nuancen der Farbstoffe außerordentlich vertieft, so daß man schon mit relativ einfachen Basen zu den für viele Verwendungszwecke wertvoll-en tiefen Bordeaux- und Granattönen gelangen kann. Da sich außerdem in dieser Reihe Farbstoffe mit guter Natronlaugekochechtheit aufbauen lassen, so stellt die Verwendung der vorliegenden Arylide eine wertvolle Bereicherung der Klasse der 2, 3-Oxvnaphthoesäurearviidfarbstoffe dar. Beispiel Gut ausgekochtes und getrocknetes Baumzn wollgarn wird mit einer Lösung von 5,5 g ?- 3-OxynaPhthOYI-4-aminoacenaphthen, 13 Teilen Natronlauge 34' B6 und io Teilen Türkischrotöl im Liter imprägniert, gründlich abgewunden und in einer mit Natriumacetat abgestumpften Diazolösung, welche 1,4 9 2-Nitroanitin im Liter enthält, entwickelt, gespült und geseift.When using: 2, 3-0-xynaphthoyl-.4-aminoacenaphthene, which has been hitherto not used for the preparation of azo dyestuffs, the shades of the dyes are extremely surprisingly over the prior art 2, 3-OXY-iiaphthoyl-i-naphthylamine deepened, so that one can get to the deep Bordeaux and garnet tones, which are valuable for many purposes, with relatively simple bases. Since dyes with good caustic soda boiling fastness can also be built up in this series, the use of the present arylides represents a valuable enrichment of the class of 2,3-Oxvnaphthoesäurearviid dyes. Example Well-boiled and dried cotton yarn is mixed with a solution of 5.5 g ? - 3-OxynaPhthOYI-4-aminoacenaphthen, 13 parts of sodium hydroxide solution 34 'B6 and 10 parts of Turkish red oil per liter impregnated, thoroughly wound and developed, rinsed and soaped in a diazo solution truncated with sodium acetate, which contains 1,4 9 2-nitroanitine per liter .

Man erhält- so eine braune Granatfärbung von guten Echtheitseigenschaften. In der gleichen Weise entsteht mit 2, 5_Dichloranilin ein Orangebraun 2, 4-Dichloranilin ein sattes Bordeaux 3 -Nitro-i, 4-toluidin ein tiefes Bordeaux 5-Nitro-2-tOlUidin ein blaues Granat 4-Nitro-2-anisidin ein Bordeaux 3-Nitro-I, 4-anisidin ein tiefes Korinth i-Am,inoanthrach.inon ein braunes Granat Dianisidin (nachgekupfert) ein dunkles Blau o-Aminoazotoluol ein tiefes blaues Korinth 5-Chlor-2-toluidi#n ein sattes blatistichiges Rot.A brown garnet dyeing with good fastness properties is obtained in this way. In the same way, with 2, 5_Dichloranilin an orange brown 2, 4-dichloroaniline a rich Bordeaux 3 -nitro-1,4-toluidine a deep Bordeaux 5-nitro-2-tOlUidin a blue garnet 4-nitro-2-anisidine a Bordeaux 3-Nitro-I, 4-anisidine a deep Corinth i-Am, inoanthrach.inon a brown garnet Dianisidine (re-coppered) a dark blue o-Aminoazotoluol a deep blue Corinth 5-chloro-2-toluidi # n a deep blue-tinged red.

Claims (1)

PATE1ITTANSPRUCH: Verfahren zur Darstellung von wasserunlöslichen Azofarbstoffen, darin b ' e stehend, daß man Diazo-, Tetrazo- oder DDiazoazoverbindungen, welche keine Sulfon- oder Carbonsäuregruppe enthalten, mit 2, 3-Oxynaphthoyl-4-,aminoacenaphthen für sich oder auf einer Grundlage kuppelt.PATE1ITTANSPRUCH: Procedure for the preparation of water-insoluble azo dyes, in 'e b standing, that diazo, tetrazo or DDiazoazoverbindungen which do not contain sulfonic or carboxylic acid group, with 2, 3-oxynaphthoyl 4-, aminoacenaphthene itself or on a basis of clutch.
DEJ35450D 1928-09-09 1928-09-09 Process for the preparation of water-insoluble azo dyes Expired DE533795C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEJ35450D DE533795C (en) 1928-09-09 1928-09-09 Process for the preparation of water-insoluble azo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEJ35450D DE533795C (en) 1928-09-09 1928-09-09 Process for the preparation of water-insoluble azo dyes

Publications (1)

Publication Number Publication Date
DE533795C true DE533795C (en) 1931-09-18

Family

ID=7205427

Family Applications (1)

Application Number Title Priority Date Filing Date
DEJ35450D Expired DE533795C (en) 1928-09-09 1928-09-09 Process for the preparation of water-insoluble azo dyes

Country Status (1)

Country Link
DE (1) DE533795C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921223C (en) * 1951-03-02 1954-12-13 Ciba Geigy Process for the preparation of acid amide derivatives of azo compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921223C (en) * 1951-03-02 1954-12-13 Ciba Geigy Process for the preparation of acid amide derivatives of azo compounds

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