DE611338C - Process for the production of halogen-containing Kuepen dyes - Google Patents

Process for the production of halogen-containing Kuepen dyes

Info

Publication number
DE611338C
DE611338C DEI48204D DEI0048204D DE611338C DE 611338 C DE611338 C DE 611338C DE I48204 D DEI48204 D DE I48204D DE I0048204 D DEI0048204 D DE I0048204D DE 611338 C DE611338 C DE 611338C
Authority
DE
Germany
Prior art keywords
halogen
production
dyes
kuepen dyes
kuepen
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
DEI48204D
Other languages
German (de)
Inventor
Dr Ernst Honold
Dr Rudolf Mueller
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 DEI48204D priority Critical patent/DE611338C/en
Application granted granted Critical
Publication of DE611338C publication Critical patent/DE611338C/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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/40—Condensation products of benzanthronyl-amino-anthraquinones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung halogenhaltiger Küpenfarbstoffe In dem zweiten Zusatzpatent 61o 849 wird ein Verfahren zur Herstellung von halogenhaltigen Küpenfarbstoffen beschrieben, das darin besteht, daß man die Küpenfarbstoffe, welche gemäß Patent 52o 876 und dessen Zusatzpatenten 522 970, 525 945 und 541 267 erhalten werden und Acylaminogruppen -enthaltende. - Kondensationsprodukte aus Benzanthronyl-i-aminoanthrachinonen darstellen, gemäß dem Verfahren des Hauptpatents mit chlorierenden Mitteln unter milden Bedingungen behandelt. Gemäß dem Verfahren des ersten Zusatzpatents 6o8 795 werden die gleichen Ausgangskörper zunächst in hochchlorierte Derivate übergeführt und aus diesen durch Chlorwasserstoffabspaltung bzw. Enthalogenierung niedrigchlorierte Farbstoffe gewonnen.Process for the production of halogen-containing vat dyes In the second additional patent 61o 849 a process for the production of halogen-containing vat dyes is described, which consists in that the vat dyes which are obtained according to patent 52o 876 and its additional patents 522 97 0 , 525 945 and 541 267 and Acylamino groups -containing. - represent condensation products of benzanthronyl-i-aminoanthraquinones, treated according to the process of the main patent with chlorinating agents under mild conditions. According to the process of the first additional patent 6o8 795, the same starting bodies are first converted into highly chlorinated derivatives and dyes with low chlorine content are obtained from these by elimination of hydrogen chloride or dehalogenation.

Es wurde nun gefunden, daß man zu ähnlichen wertvollen Farbstoffen gelangt, welche im Vergleich zu den Ausgangskörpern ebenfalls durch eine nach blau verschobene Nuance und verbesserte Chlorechtheit der damit erzielten Färbungen ausgezeichnet sind, wenn man die obigen Ausgangskörper einer Bromierung unter milden Bedingungen unterwirft. Beispiel 25 kg des Farbstoffes, erhalten gemäß Patent 520 876, Beispiel i, werden in fein verteilter Form mit einer Lösung von 16 kg Brom in etwa Zoo kg Eisessig bei Gegenwart von 25 kg Natriumacetat und einer geringen Menge Jod versetzt, und die Mischung wird dann längere Zeit gerührt. Hierauf wird die Reaktionsmasse zum Kochen erhitzt und unter Rückflußkühlung noch etwa 3 Stunden gekocht. Nach Absaugen und Auswaschen wird ein Farbstoff erhalten, der ungefähr i i bis 12 % Brom enthält und der, aus Schwefelsäure gelöst, aus blauvioletter Küpe Baumwolle in echten olivfarbenen Tönen färbt, die wesentlich blauer sind als die des Ausgangsfarbstoffes. Bei starker Einwirkung von Chlorlauge auf -die Färbung ist eine gegenüber dem Ausgangsmaterial verbesserte Chlorechtheit festzustellen. Die Lösungsfarbe in konzentrierter Schwefelsäure ist grün.It has now been found that similar valuable dyes can be obtained which, in comparison to the original bodies, also goes through a to blue The shifted shade and improved chlorine fastness of the dyeings obtained therewith are excellent are, if one of the above starting bodies a bromination under mild conditions subject. Example 25 kg of the dye obtained according to patent 520,876, example i, are finely divided with a solution of 16 kg of bromine in about zoo kg Glacial acetic acid added in the presence of 25 kg of sodium acetate and a small amount of iodine, and the mixture is then stirred for a long time. The reaction mass then becomes heated to a boil and refluxed for about 3 hours. After suction and washing out a dye is obtained which contains about i i to 12% bromine and that, dissolved from sulfuric acid, from blue-violet cotton vat in real olive-colored Colors that are much bluer than that of the original dye. With strong Effect of chlorine lye on -the coloration is opposite to that of the starting material detect improved chlorine fastness. The solution paint in concentrated sulfuric acid is green.

Zu ähnlichen Farbstoffen gelangt man, wenn man die Bromierung nach anderen Methoden durchführt, z. B. durch Einwirkung von Brom in Tetrachloräthan oder Nitrobenzol als Suspensionsmittel mit oder ohne Zusatz von Jod als Katalysator.One arrives at similar dyes if one follows the bromination other methods, e.g. B. by the action of bromine in tetrachloroethane or nitrobenzene as a suspending agent with or without the addition of iodine as a catalyst.

Claims (1)

PATENTANSPRUCH Abänderung des Verfahrens des Hauptpätents 602 402 und des zweiten Zusatzpatents 61o849, dadurch gekennzeichnet, daB die gemäß Patent 520 876 und seiner Zusätze 5z2 970, 525 945 und 541 267 erhältlichen Küpenfarbstoffe einer Bromierung unter milden Bedhigungen unterworfen werden.PATENT CLAIM Modification of the process of the main patent 602 402 and the second additional patent 61o849, characterized in that the vat dyes obtainable according to patent 520 876 and its additions 5z2 97 0 , 525 945 and 541 267 are subjected to bromination under mild conditions.
DEI48204D 1933-10-26 1933-10-26 Process for the production of halogen-containing Kuepen dyes Expired DE611338C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI48204D DE611338C (en) 1933-10-26 1933-10-26 Process for the production of halogen-containing Kuepen dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI48204D DE611338C (en) 1933-10-26 1933-10-26 Process for the production of halogen-containing Kuepen dyes

Publications (1)

Publication Number Publication Date
DE611338C true DE611338C (en) 1935-03-26

Family

ID=7192194

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI48204D Expired DE611338C (en) 1933-10-26 1933-10-26 Process for the production of halogen-containing Kuepen dyes

Country Status (1)

Country Link
DE (1) DE611338C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1095968B (en) * 1957-05-13 1960-12-29 Bayer Ag Process for the production of Kuepen dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1095968B (en) * 1957-05-13 1960-12-29 Bayer Ag Process for the production of Kuepen dyes

Similar Documents

Publication Publication Date Title
DE611338C (en) Process for the production of halogen-containing Kuepen dyes
DE432801C (en) Process for the preparation of 2-chloro-4-nitro-1-aminobenzene
DE582613C (en) Process for the production of asymmetrical indigoid dyes
DE565247C (en) Process for the preparation of a Kuepen dye
DE554322C (en) Process for the preparation of Kuepen dyes of the 1íñ2-Benzanthraquinone series
DE610849C (en) Process for the production of halogen-containing Kuepen dyes
DE622656C (en) Process for the production of water-insoluble azo dyes
DE508108C (en) Process for the preparation of Kuepen dyes of the pyranthrone series
DE396111C (en) Process for the preparation of chlorine-free derivatives of N-dihydroanthraquinone azine
DE729230C (en) Process for printing animal fibers or cellulose fibers or fiber mixtures thereof with chromium stain dyes
DE526737C (en) Process for the preparation of Kuepen dyes of the N-dihydro-1íñ2íñ2'íñ1'-anthraquinonazine series
DE518230C (en) Process for the preparation of Kuepen dyes of the N-dihydro-1, 2, 2, 1-anthraquinonazine series
DE651249C (en) Process for the production of Kuepen dyes
DE536294C (en) Process for the preparation of Kuepen dyes of the anthraquinone series
DE484273C (en) Process for the preparation of Kuepen dyes
AT149664B (en) Process for the production of acidic dyes of the naphthophenosafranin series.
DE486517C (en) Process for the preparation of Kuepen dyes
DE441984C (en) Process for developing Kuepen dyes on the fiber
DE625851C (en) Process for the production of water-insoluble azo dyes
DE958947C (en) Process for the production of halogen-containing Kuepen dyes
DE645603C (en) Process for dyeing blended fabrics made from acetate silk and animal fibers
DE621475C (en) Process for the production of nitrodibenzanthrones
DE1174926B (en) Process for the preparation of a Kuepen dye
CH178544A (en) Process for the production of a brominated vat dye.
CH189315A (en) Process for the production of a new anthraquinone dye.