DE1032865B - Process for the production of cobalt-containing monoazo dyes - Google Patents

Process for the production of cobalt-containing monoazo dyes

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Publication number
DE1032865B
DE1032865B DEB38187A DEB0038187A DE1032865B DE 1032865 B DE1032865 B DE 1032865B DE B38187 A DEB38187 A DE B38187A DE B0038187 A DEB0038187 A DE B0038187A DE 1032865 B DE1032865 B DE 1032865B
Authority
DE
Germany
Prior art keywords
cobalt
dyes
monoazo dyes
alkyl
oxynaphthalene
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
DEB38187A
Other languages
German (de)
Inventor
Dr Helmut Pfitzner
Dr Otto Kaufmann
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEB38187A priority Critical patent/DE1032865B/en
Publication of DE1032865B publication Critical patent/DE1032865B/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14Monoazo compounds
    • C09B45/20Monoazo compounds containing cobalt

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

Description

Verfahren zur Herstellung von kobalthaltigen Monoazofarbstoffen Es wurde gefunden, daß man wertvolle kobalthaltige Monoazofarbstoffe in vorteilhafter Weise herstellen kann, indem man diazotierte Aminobenzole der allgemeinen Formel in der V und Z Wasserstoff, Alkyl- oder Arylgruppen und R und R' gleiche oder verschiedene niedrigmolekulare Alkylgruppen bedeuten, mit 2-Oxynaphthalin oder seinen Alkyl-, Halogen- und bzw. oder Alkoxyderivaten kuppelt und die erhaltenen o-Oxy-o'-alkoxymonoazofarbstoffe nach an sich bekannten Verfahren in Kobaltkomplexverbindungen der entsprechenden o,o'-Dioxyazofarbstoffe überführt, die auf 2 Azofarbstoffmoleküle etwa 1 Kobaltatom enthalten.Process for the preparation of cobalt-containing monoazo dyes It has been found that valuable cobalt-containing monoazo dyes can be prepared in an advantageous manner by using diazotized aminobenzenes of the general formula in which V and Z are hydrogen, alkyl or aryl groups and R and R 'are identical or different low molecular weight alkyl groups, are coupled with 2-oxynaphthalene or its alkyl, halogen and / or alkoxy derivatives and the o-oxy-o'- alkoxymonoazo dyes converted by processes known per se into cobalt complex compounds of the corresponding o, o'-dioxyazo dyes which contain about 1 cobalt atom for every 2 azo dye molecules.

Geeignete Azokomponenten sind z. B. das 2-Oxynaphthalin, das 4,8-Dichlor-2-oxvnaphthalin, das 2-Oxy-6-bromnaphthalin, das 3- oder 6-Methyl-2-oxynaphthalin oder das 2-Oxy-6-methoxynaphthalin.Suitable azo components are, for. B. 2-oxynaphthalene, 4,8-dichloro-2-oxynaphthalene, 2-oxy-6-bromonaphthalene, 3- or 6-methyl-2-oxynaphthalene or 2-oxy-6-methoxynaphthalene.

Die Umwandlung in die Kobaltkomplexverbindungen kann z. B. nach den in den deutschen Patentschriften 715 082 oder 715 948 oder in der französischen Patentschrift 836 257 beschriebenen Verfahren vorgenommen werden.The conversion into the cobalt complex compounds can e.g. B. after the in German patents 715 082 or 715 948 or in French Patent 836 257 described method can be made.

Die so erhältlichen kobalthaltigen Farbstoffe zeichnen sich durch hohe Echtheiten und gutes Egalisiervermögen aus und sind insbesondere zum Färben von Wolle und Polyamidfasern aus neutralem oder schwach saurem Bade geeignet.The cobalt-containing dyes obtainable in this way are distinguished by high fastness properties and good leveling properties and are particularly useful for dyeing Suitable for wool and polyamide fibers from neutral or slightly acidic baths.

Die gemäß der Erfindung hergestellte Kobaltkomplexverbindung der Azofarbstoffs 1,4-Dimethoxy-2-aminobenzol-5-sulfonsäureamid -- 2-Oxynaphthalin ist, auf Wolle gefärbt, besser lichtecht als die entsprechende Chromkomplexverbindung, die aus Beispiels der britischen Patentschrift 681653 bekannt ist. Die gleiche Wollfärbung des gleichen erfindungsgemäßen Farbstoffs ist auch besser walkecht als die der Kobaltkomplexverbindung des Azofarbstoffs 1-Oxy-2-amino-4-methylbenzol-5-sulfonsäureamid -@ 2-Oxynaphthalin, die in der Tabelle der deutschen Patentschrift 937 367 als Nr. 14 genannt ist.The cobalt complex compound of the azo dye 1,4-dimethoxy-2-aminobenzene-5-sulfonic acid amide - 2-oxynaphthalene prepared according to the invention is, when dyed on wool, better lightfast than the corresponding chromium complex compound known from the example of British patent 681653. The same wool dyeing of the same dye according to the invention is also better than that of the cobalt complex compound of the azo dye 1-oxy-2-amino-4-methylbenzene-5-sulfonic acid amide - @ 2-oxynaphthalene, which is listed in the table of German patent 937 367 as no. 14 is mentioned.

Die im Beispiel genannten Teile sind Gewichtsteile. Beispiel 23,2 Teile 1,4-Dimethoxy-2-aminobenzol-5-sulfonsäureamid werden in üblicher Weise dianotiert und mit einer alkalischen Lösung von 14,4 Teilen 2-Oxynaphthalin gekuppelt.The parts mentioned in the example are parts by weight. Example 23.2 Parts of 1,4-dimethoxy-2-aminobenzene-5-sulfonic acid amide are dianotized in the usual way and coupled with an alkaline solution of 14.4 parts of 2-oxynaphthalene.

20 Teile. des so erhaltenen Monoazofarbstoffs werden mit einer Lösung von 6 Teilen Kobalt(II)-chlorid (Co C12 . 6 H2 O) in 200 Teilen Acetamid 5 Stunden auf 130°C erhitzt. Dann trägt man das Gemisch in 2000 Teile Wasser ein, fällt den kobalthaltigen Farbstoff mit 200 Teilen Natriumchlorid aus, saugt ab, wäscht mit etwas Wasser und trocknet bei 80°C.20 parts. of the monoazo dye thus obtained are mixed with a solution of 6 parts of cobalt (II) chloride (Co C12. 6 H2 O) in 200 parts of acetamide for 5 hours heated to 130 ° C. Then the mixture is introduced into 2000 parts of water, the falls cobalt-containing dye with 200 parts of sodium chloride, filtered off with suction, washed with some water and dry at 80 ° C.

Der so hergestellte kobalthaltige Farbstoff färbt Wolle und Polyamidfasern aus schwach saurem Bade in blaustichig violetten Tönen von sehr guten Echtheiten.The cobalt-containing dye produced in this way dyes wool and polyamide fibers from a weakly acidic bath in bluish violet shades of very good fastness properties.

In entsprechender Weise kann man kobalthaltige Farbstoffe aus den folgenden Komponenten herstellen Färbung der Kobalt- Diazokomponente Azokomponente komplexverbindung auf Wolle 1,4-Dimethoxy-2- 2-Oxy-6-brom- Blauviolett aminobenzol-5- naphthalin sulfonsäureamid 1,4-Diäthoxy-2- 2-Oxy-6-methoxy- Blau aminobenzol-5- naphthalin sulfonsäureamid In a corresponding manner, cobalt-containing dyes can be prepared from the following components Coloring of the cobalt Diazo component Azo component complex compound on wool 1,4-dimethoxy-2- 2-oxy-6-bromo-blue-violet aminobenzene-5-naphthalene sulfonic acid amide 1,4-diethoxy-2-oxy-6-methoxy blue aminobenzene-5-naphthalene sulfonic acid amide

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von kobalthaltigen Monoazofarbstoffen, dadurch gekennzeichnet, daß man diazotierte Aminobenzole der allgemeinen Formel in der V und Z Wasserstoff, Alkyl- oder Arylgruppen und R und R' gleiche oder verschiedene niedrigmolekulare Alkylgruppen bedeuten, mit 2-Oxynaphthalin oder seinen Alkyl-, Halogen- und bzw. oder Alkoxyderivaten kuppelt und die erhaltenen o-Oxy-o'-alkoxy monoazofarbstoffe in Kobaltkomplexverbindungen der entsprechenden o,o'-Dioxyazofarbstoffe überführt, die auf 2 Azofarbstoffmoleküle etwa 1 Kobaltatom enthalten. In Betracht gezogene Druckschriften: Deutsche Patentanmeldung C 6261 IVb,l22a (bekanntgemacht am 5. B. 1954), britische Patentschrift Nr. 681653. Bei der Bekanntmachung der Anmeldung sind zwei Färbetafeln mit Erläuterungen ausgelegt worden.PATENT CLAIM: Process for the preparation of cobalt-containing monoazo dyes, characterized in that diazotized aminobenzenes of the general formula in which V and Z are hydrogen, alkyl or aryl groups and R and R 'are identical or different low molecular weight alkyl groups, are coupled with 2-oxynaphthalene or its alkyl, halogen and / or alkoxy derivatives and the o-oxy-o'- alkoxy monoazo dyes converted into cobalt complex compounds of the corresponding o, o'-dioxyazo dyes, which contain about 1 cobalt atom for every 2 azo dye molecules. Considered publications: German patent application C 6261 IVb, 122a (published on 5th B. 1954), British patent specification No. 681653. When the application was published, two color tables were laid out with explanations.
DEB38187A 1955-12-07 1955-12-07 Process for the production of cobalt-containing monoazo dyes Pending DE1032865B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB38187A DE1032865B (en) 1955-12-07 1955-12-07 Process for the production of cobalt-containing monoazo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB38187A DE1032865B (en) 1955-12-07 1955-12-07 Process for the production of cobalt-containing monoazo dyes

Publications (1)

Publication Number Publication Date
DE1032865B true DE1032865B (en) 1958-06-26

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEB38187A Pending DE1032865B (en) 1955-12-07 1955-12-07 Process for the production of cobalt-containing monoazo dyes

Country Status (1)

Country Link
DE (1) DE1032865B (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB681653A (en) * 1950-06-29 1952-10-29 Du Pont Improvements in azo dye

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB681653A (en) * 1950-06-29 1952-10-29 Du Pont Improvements in azo dye

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