DE441439C - Process for the preparation of indigoid dyes - Google Patents

Process for the preparation of indigoid dyes

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Publication number
DE441439C
DE441439C DEK91104D DEK0091104D DE441439C DE 441439 C DE441439 C DE 441439C DE K91104 D DEK91104 D DE K91104D DE K0091104 D DEK0091104 D DE K0091104D DE 441439 C DE441439 C DE 441439C
Authority
DE
Germany
Prior art keywords
preparation
weight
dyes
parts
isatin
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
DEK91104D
Other languages
German (de)
Inventor
Dr Otto Herrmann
Dr Maximilian P Schmidt
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.)
Kalle GmbH and Co KG
Original Assignee
Kalle GmbH and Co KG
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 Kalle GmbH and Co KG filed Critical Kalle GmbH and Co KG
Priority to DEK91104D priority Critical patent/DE441439C/en
Application granted granted Critical
Publication of DE441439C publication Critical patent/DE441439C/en
Expired 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
    • C09B7/00—Indigoid dyes
    • C09B7/08—Other indole-indigos

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

Description

Verfahren zur Darstellung von indigoiden Küpenfarbstoffen. In den Patentschriften 241 997 und 269 123 sinn indigoide Küpenfarbstoffe, die durch Kondensation von Isatin-a-derivaten mit Oxynaphthocarbazolen ,entstehen, beschrieben. Diese Küpenfarbstoffe eignen sich wegen ihres trüben Tones vorzüglich zur Darstellung von grauen .oder schwarzen Färbungen.Process for the preparation of indigoid vat dyes. In the patents 241 997 and 269 123 sense indigoid vat dyes, which are formed by condensation of isatin-α-derivatives with oxynaphthocarbazoles, are described. Because of their cloudy tone, these vat dyes are ideally suited for the representation of gray or black colors.

Es ist nun gefunden worden, daß die hydrierten Oxynaphthocarbazole, die durch Einwirkung von hydroaromatischen Ringketonen auf Arylhydrazinsulfosäuren und nachträg. licher Verschmelzung entstehen, bei der Kondensation mit Isarin-a-derivaten überraschenderweise wertvolle Küpenfarbstoffe von ähnlichen Eigenschaften, aber besserer Chlorechtheit, geben.It has now been found that the hydrogenated oxynaphthocarbazoles, those caused by the action of hydroaromatic ring ketones on arylhydrazine sulfonic acids and afterwards. Licher amalgamation arise during the condensation with isarin-a-derivatives Surprisingly valuable vat dyes of similar properties, but better chlorine fastness.

Als Isatin-a-derivate kommen nicht nur die a-Derivate des Isatins selbst in Betracht, sondern auch die der Substitutionsprodukte, Homologe und Analoge.The isatin a-derivatives are not just the a-derivatives of isatin themselves into consideration, but also those of the substitution products, homologs and analogs.

Beispiele. i. 11,8 Gewichtsteile 5 - Oxy - 2, i - (tetrahydropheno-)naphthocarbazol werden mit 16 Gewichtsteilen Chlorisatinanilid in i2o Gewichtsteilen Essigsäureanhydrid i Stunde lang auf 8o bis ioo° erhitzt. Der ausfallende Farbstoff wird durch Auswaschen mit Benzol und Alkohol rein erhalten. Er ist in Schwefelsäure mit blauer Farbe löslich und färbt aus hellgelber Küpe Wolle und Baumwolle in trüben, blauvioletten Tönen an.Examples. i. 11.8 parts by weight of 5 - oxy - 2, i - (tetrahydropheno-) naphthocarbazole are heated with 1 6 parts by weight Chlorisatinanilid in i2o parts by weight of acetic anhydride i hour on 8o to ioo °. The precipitated dye is obtained in pure form by washing it out with benzene and alcohol. It is soluble in sulfuric acid with a blue color and dyes wool and cotton in cloudy, blue-violet shades from a light yellow vat.

z. 11,8 Gewichtsteile 5 - Oxy - i, a - (tetrahydropheno-)naphthocarbazol werden mit 1q. Gewichtsteilen Isatinanilid, wie in Beispiel i, zum Farbstoff kondensiert. Er färbt Wolle und Baumwolle in grauen Tönen an. Beim Bromieren mit der gleichen Gewichtsmenge Brom in der zehnfachen Gewichtsmenge Eisessig geht er in einen Farbstoff von noch besseren Echtheitseigenschaften über, der in Schwefelsäure mit blauer Farbe löslich ist und Wolle und Baumwolle aus gelber Küpe in trüben blauen Tönen anfärbt.z. 11.8 parts by weight of 5 - oxy - i, a - (tetrahydropheno-) naphthocarbazole are with 1q. Parts by weight of isatin anilide, as in Example i, condensed to form the dye. He dyes wool and cotton in gray tones. When brominating with the same Weight amount of bromine in ten times the amount by weight of glacial acetic acid, it goes into a dye of even better fastness properties over that in sulfuric acid with a blue color is soluble and dyes wool and cotton from a yellow vat in cloudy blue tones.

3. 12,5 Gewichtsteile 5-Oxy-a, i-(methvltetrahydropheno-)naphthocarbazol «-erden mit 14 Gewichtsteilen Isatinanilnd, wie im Beispiel i, kondensiert. Der entstehende Farbstoff gibt mit Schwefelsäure eine blaue Lösung und liefert auf Wolle und Baumwolle trübe, blauviolette Färbungen.3. 12.5 parts by weight of 5-oxy-a, i- (methyltetrahydropheno-) naphthocarbazole - earth with 14 parts by weight of isatin anilnd, as in example i, condensed. Of the The resulting dye gives a blue solution with sulfuric acid and delivers on wool and cotton cloudy, blue-violet colorations.

Die Farbstoffe lassen sich, wie weiter festgestellt worden ist, auch nachhalogenieren.As has been further stated, the dyes can also be used re-halogenate.

Claims (1)

VATRNTANSPRUCH: Verfahren zur Darstellung von indigoiden Küpenfarbstoffen, dadurch gekennzeichnet, daß hydrierte Oxynaphtho-carbazole mit Isatin-a-derivaten (einschließlich der Substitutionsprodukte, Homologen und Analogen) kondensiert und die erhaltenen Produkte gegebenenfalls halogeniert werden.CLAIM: Process for the preparation of indigoid vat dyes, characterized in that hydrogenated oxynaphtho-carbazoles with isatin-a-derivatives (including the substitution products, homologues and analogs) condensed and the products obtained are optionally halogenated.
DEK91104D 1924-09-27 1924-09-27 Process for the preparation of indigoid dyes Expired DE441439C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEK91104D DE441439C (en) 1924-09-27 1924-09-27 Process for the preparation of indigoid dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK91104D DE441439C (en) 1924-09-27 1924-09-27 Process for the preparation of indigoid dyes

Publications (1)

Publication Number Publication Date
DE441439C true DE441439C (en) 1927-03-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEK91104D Expired DE441439C (en) 1924-09-27 1924-09-27 Process for the preparation of indigoid dyes

Country Status (1)

Country Link
DE (1) DE441439C (en)

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