DE593632C - Process for the production of azo dyes - Google Patents

Process for the production of azo dyes

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Publication number
DE593632C
DE593632C DEI45295D DEI0045295D DE593632C DE 593632 C DE593632 C DE 593632C DE I45295 D DEI45295 D DE I45295D DE I0045295 D DEI0045295 D DE I0045295D DE 593632 C DE593632 C DE 593632C
Authority
DE
Germany
Prior art keywords
azo dyes
weight
parts
production
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
DEI45295D
Other languages
German (de)
Inventor
Dr Gerhard Schrader
Dr Hugo Schweitzer
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 DEI45295D priority Critical patent/DE593632C/en
Application granted granted Critical
Publication of DE593632C publication Critical patent/DE593632C/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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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

Description

Es wurde gefunden, daß man zu wertvollen gelben Baumwollfarbstoffen gelangt, wenn man die Diazoverbindungen von Sulfonsäuren von Aminothiazolen, wie z. B. Dehydrothiotoluidin, Dehydrothioxylidin, Primulin, ihren Substitutionsprodukten und Derivaten, mit Acetessigsäureamiden kuppelt, in denen ein Wasserstoffatom der Amidgruppe durch den Benzothiazolrest oder einen substituierten Benzothiazolrest ersetzt ist.It has been found that valuable yellow cotton dyes can be obtained by the diazo compounds of sulfonic acids of aminothiazoles, such as. B. dehydrothiotoluidine, Dehydrothioxylidine, primulin, their substitution products and derivatives, with acetoacetic acid amides couples, in which a hydrogen atom of the amide group is replaced by the benzothiazole radical or a substituted benzothiazole radical is replaced.

Die so erhältlichen Farbstoffe haben neben guter Klarheit des Farbtons und guter Lichtechtheit gegenüber den bekannten Farbstoffen aus Dehydrothiotoluidinsulfonsäuren und Acet-The dyes obtainable in this way have not only good color shade clarity and good lightfastness compared to the known dyes from dehydrothiotoluidinsulfonic acids and acet-

CHS essigsäurearyliden den großen technischen Vorzug, daß sie neutral reinweiß ätzbar und außerdem avivierecht sind.CH S acetic acid arylides have the great technical advantage that they can be etched in a neutral, pure white and are also avivier-proof.

Beispiel 1example 1

44,4 Gewichtsteile dehydrothiotoluidindisulfonsaures Natrium werden, wie üblich, mit 6,9 Gewichtsteilen Natriumnitrit bei Gegenwart von 35 Gewichtsteilen roher Salzsäure diazotiert. Diese Diazolösung läßt man alsdann in eine mit 20 Gewichtsteilen krystallisiertem Natriumacetat versetzte wäßrige Suspension ^0 von 24,8 Gewichtsteilen 2-Acetoacetylamino-4-methylbenzothiazol von der Formel44.4 parts by weight of sodium dehydrothiotoluidindisulfonsaures are, as usual, diazotized with 6.9 parts by weight of sodium nitrite in the presence of 35 parts by weight of crude hydrochloric acid. This diazo solution is then allowed to crystallized in a 20 parts by weight of sodium acetate offset aqueous suspension 0 ^ 24.8 weight parts of 2-acetoacetylamino-4-methyl benzothiazole of the formula

/i/ i

2C-NH-CO —CH,-CO-CHo 2 C-NH-CO-CH, -CO-CHo

einlaufen.come in.

Ist die Kupplung beendet, so filtriert man den Farbstoff ab und arbeitet ihn nach bekannten Methoden auf. Er färbt auf Baumwolle ein grünstichiges Gelb, das eine gute Licht- und Avivierechtheit zeigt und sich neutral reinweiß ätzen läßt. When the coupling has ended, the dye is filtered off and it is worked according to known methods Methods on. It dyes cotton a greenish yellow, which is good light and It shows that it is fast to release and can be etched in a neutral, pure white.

Verwendet man an Stelle des obigen Benzothiazole das 2-Acetoacetylaminobenzothiazol oder 2 - Acetoacetylamino - 6 - methoxybenzothi-If 2-acetoacetylaminobenzothiazole is used instead of the above benzothiazole or 2 - acetoacetylamino - 6 - methoxybenzothi-

*) Von dein Patentsucher sind als die Erfinder angegeben worden: Dr. Hugo Schweitzer in Leverkusen-Wiesdorf und Dr. Gerhard S ehr ader in Opladen, RhId.*) Your patent seeker stated that the inventors were: Dr. Hugo Schweitzer in Leverkusen-Wiesdorf and Dr. Gerhard Ehrader in Opladen, RhId.

azol oder 2-x\cetoaeetylamino-6~äthoxybenzothiazol oder 2-Acetoacetylamino-4-methoxybenzothiazol oder 2-Acetoacetylamino-6-methyibenzothiazol,. so erhält man Farbstoffe von ähnlichen Eigenschaften.azole or 2-x \ cetoaeetylamino-6 ~ ethoxybenzothiazole or 2-acetoacetylamino-4-methoxybenzothiazole or 2-acetoacetylamino-6-methyibenzothiazole ,. this gives dyes with similar properties.

Beispiel 2Example 2

44,4 Gewichtsteile dehydrothiotoluidindisulfonsaures Natrium werden, wie in Beispiel 1 angegeben, diazotiert. Die Diazoverbindung läßt man in eine mit 20 Gewichtsteilen krystallisiertem Natriumacetat versetzte wäßrige Suspension von 24,8 Gewichtsteilen 6-Acetoacetylamino-2-ihethylbenzothiazol einlaufen. Ist die Kupplung beendet, so wird der Farbstoff wie üblich aufgearbeitet. Er färbt auf Baumwolle ein avivier- und lichtechtes Gelb, das sich neutral reinweiß ätzen läßt.44.4 parts by weight of dehydrothiotoluidinedisulfonic acid As indicated in Example 1, sodium is diazotized. The diazo compound is left in an aqueous suspension mixed with 20 parts by weight of crystallized sodium acetate of 24.8 parts by weight of 6-acetoacetylamino-2-ihethylbenzothiazole come in. When the coupling has ended, the dye is worked up as usual. He dyes on cotton an avivier and lightfast yellow that can be etched in a neutral, pure white.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von Azofarbstoffen, dadurch gekennzeichnet, daß man die Diazoverbindungen von Sulfonsäuren von Aminobenzothiazolen bzw. ihren Substitutionsprodukten mit Acetessigsäureamiden kuppelt, in denen ein Wasserstoffatom der Amidgruppe durch den Benzothiazolrest bzw.. einen substituierten Benzothiazolrest ersetzt ist.Process for the preparation of azo dyes, characterized in that one the diazo compounds of sulfonic acids of aminobenzothiazoles or their substitution products with acetoacetic acid amides, in which a hydrogen atom of Amide group through the benzothiazole residue or a substituted benzothiazole residue is replaced.
DEI45295D 1932-09-10 1932-09-10 Process for the production of azo dyes Expired DE593632C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI45295D DE593632C (en) 1932-09-10 1932-09-10 Process for the production of azo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI45295D DE593632C (en) 1932-09-10 1932-09-10 Process for the production of azo dyes

Publications (1)

Publication Number Publication Date
DE593632C true DE593632C (en) 1934-03-03

Family

ID=7191496

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI45295D Expired DE593632C (en) 1932-09-10 1932-09-10 Process for the production of azo dyes

Country Status (1)

Country Link
DE (1) DE593632C (en)

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