DE818221C - Process for the preparation of yellow monoazo dyes - Google Patents

Process for the preparation of yellow monoazo dyes

Info

Publication number
DE818221C
DE818221C DEP35044A DEP0035044A DE818221C DE 818221 C DE818221 C DE 818221C DE P35044 A DEP35044 A DE P35044A DE P0035044 A DEP0035044 A DE P0035044A DE 818221 C DE818221 C DE 818221C
Authority
DE
Germany
Prior art keywords
yellow
preparation
monoazo dyes
pyrazolone
methyl
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
DEP35044A
Other languages
German (de)
Inventor
Richard Dr Fleischhauer
Werner Dr Zerweck
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEP35044A priority Critical patent/DE818221C/en
Application granted granted Critical
Publication of DE818221C publication Critical patent/DE818221C/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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von gelben Monoazofarbstoffen Es wurde gefunden, daß man wertvolle neue wasserunlösliche gelbe Monoazofarbstoffe erhält; wenn .man die Diazoverbindungen von Aminodiphenylmethanen mit einer Gelbkomponente, die keine Carboxyl- oder Sulfonsäuregruppe enthält, kuppelt.Process for the preparation of yellow monoazo dyes It has been found that valuable new water-insoluble yellow monoazo dyes are obtained; if the diazo compounds of aminodiphenylmethanes with a yellow component that does not contain any Contains carboxyl or sulfonic acid group, couples.

Diese Farbstoffe sind in Wasser unlöslich, aber in organischen Lösungsmitteln gut löslich. Sie lassen sich zum Färben von Ko-hlenwasserstoffen, Kerzen, Lacken und zur Herstellung von Druckfarben verwenden. Da die bei letzterer Verwendungsart erhaltenen Buntdrucke eine beachtliche Sublimierechtheit aufweisen, sind die Farbstoffe vorliegender Erfindung besonders für den Doppeltondruck geeignet. Beispiel: 19,7 kg 2-Aminodiphenylmethan werden mit überschüssiger Salzsäure in Lösung gebracht. Nach dem Abkühlen auf o° wird in üblicher Weise mit Natriumnitrit diazotiert. Die Diazolösung wird mit einer sodaalkalischen Lösung von 17,5 kg 1-Phenyl-3-methyl-5-pyrazolon vereinigt. Der Farbstoff, der sich sofort gebildet hat, wird abfiltriert und getrocknet. Er stellt ein gelbes wasserunlösliches Pulver dar, welches sich in organischen Lösungsmitteln mit grünstickig gelber Farbe löst.These dyes are insoluble in water but are insoluble in organic solvents easily soluble. They can be used for coloring hydrocarbons, candles, paints and use to make printing inks. Since the latter is used The color prints obtained have considerable fastness to sublimation, are the dyes The present invention is particularly suitable for double-tone printing. Example: 19.7 kg of 2-aminodiphenylmethane are brought into solution with excess hydrochloric acid. After cooling to 0 °, sodium nitrite is used for diazotization in the usual way. the Diazo solution is mixed with a soda-alkaline solution of 17.5 kg of 1-phenyl-3-methyl-5-pyrazolone united. The dye that has formed immediately is filtered off and dried. It is a yellow, water-insoluble powder that dissolves in organic solvents dissolves with a greenish yellow color.

Der Farbstoff färbt Stearin oder Paraffin in grünstickig gelben Farbtönen. Die Färbungen besitzen eine gute Sublimierechtheit, so daB der Farbstoff für den sogenannten Doppeltondruck geeignet ist.The dye colors stearin or paraffin in greenish yellow shades. The dyeings have good sublimation fastness, so that the dye for the so-called double-tone printing is suitable.

Andere gelbe Farbstoffe von ähnlichen Eigen,-schaften erhält man, wenn man das 1-Phenyl-3-methyl-5-pyrazolon durch äquivalente Mengen von anderen Pyrazolonen, z. B.Other yellow dyes of similar properties are obtained if you substitute the 1-phenyl-3-methyl-5-pyrazolone with equivalent amounts of others Pyrazolones, e.g. B.

3-Methyl-5-pyrazolon, 1(2'-Chlorphenyl)-3-methyl-5-pyrazolon, t (3'-Chlorphenyl)-3-methyl-5-pyrazolon, 1(4'-Chlorphenyl)-3-methyl-5-pyrazolon, 1(2', 5'-Dichlorphenyl)-3-methyl-5-pyrazolon ersetzt. Werden als Azokomponenten Acetessigsäurearylamide verwendet, so erhält rvan gleichfalls grünstichig gelb färbende Produkte, während mit N-Dimethylanilin ein etwas rotstichiger gelb färbender Farbstoff von ähnlichen Eigenschaften gewonnen wird.3-methyl-5-pyrazolone, 1 (2'-chlorophenyl) -3-methyl-5-pyrazolone, t (3'-chlorophenyl) -3-methyl-5-pyrazolone, 1 (4'-chlorophenyl) -3-methyl-5-pyrazolone, 1 (2 ', 5'-dichlorophenyl) -3-methyl-5-pyrazolone replaced. If acetoacetic acid arylamides are used as azo components, in this way rvan also receives greenish-tinged yellow products, while with N-dimethylaniline obtained a somewhat reddish yellow coloring material with similar properties will.

An Stelle von 2-Amirwdiphenylmethan kann man auch z. B. 4-Aminodiphenylmethan verwenden.Instead of 2-Amirwdiphenylmethan you can z. B. 4-aminodiphenylmethane use.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von gelben Monoazofarbstoffen, dadurch gekennzeichnet, daB man die Diazoverbindungen von Aminodiphenylmethanen mit einer Gelbkomponente, die keine Carboxyl- oder Sulfonsäuregruppe enthält, kuppelt.PATENT CLAIM: Process for the production of yellow monoazo dyes, characterized in that the diazo compounds of aminodiphenylmethanes with a yellow component that does not contain any carboxyl or sulfonic acid groups.
DEP35044A 1949-02-25 1949-02-25 Process for the preparation of yellow monoazo dyes Expired DE818221C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP35044A DE818221C (en) 1949-02-25 1949-02-25 Process for the preparation of yellow monoazo dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP35044A DE818221C (en) 1949-02-25 1949-02-25 Process for the preparation of yellow monoazo dyes

Publications (1)

Publication Number Publication Date
DE818221C true DE818221C (en) 1951-10-22

Family

ID=7374009

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP35044A Expired DE818221C (en) 1949-02-25 1949-02-25 Process for the preparation of yellow monoazo dyes

Country Status (1)

Country Link
DE (1) DE818221C (en)

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