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DE532079C - Process for the production of azo dyes - Google Patents

Process for the production of azo dyes

Info

Publication number
DE532079C
DE532079C DEG73833D DEG0073833D DE532079C DE 532079 C DE532079 C DE 532079C DE G73833 D DEG73833 D DE G73833D DE G0073833 D DEG0073833 D DE G0073833D DE 532079 C DE532079 C DE 532079C
Authority
DE
Germany
Prior art keywords
production
azo dyes
carboxylic acid
pyrazolone
diazotized
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
DEG73833D
Other languages
German (de)
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 Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Application granted granted Critical
Publication of DE532079C publication Critical patent/DE532079C/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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/12—Disazo dyes from other coupling components "C"
    • C09B31/14—Heterocyclic components

Landscapes

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

Description

Verfahren zur Herstellung von Azofarbstoffen Es wurde gefunden, daß man neue wertvolle Farbstoffe erhält, wenn man Diazoniumverbindungen, welche weder Sulfon- noch Carbonsäuregruppen enthalten und die sich von chromophore Gruppen enthaltenden primären aromatischen Aminen ableiten, mit Estern der 5-Pyrazolon-3-carbonsäure kuppelt. Solche Ester entstehen, wenn man Oxalessigester mit Hydrazin kondensiert.Process for the preparation of azo dyes It has been found that you get new valuable dyes if you diazonium compounds, which neither Sulphonic or carboxylic acid groups and those containing chromophoric groups Derive primary aromatic amines with esters of 5-pyrazolone-3-carboxylic acid clutch. Such esters are formed when oxaloacetic esters are condensed with hydrazine.

Infolge der Löslichkeit dieser Farbstoffe in verschiedenen organischen Lösungsmittehl können dieselben zur Herstellung von gefärbten Lacken verwendet werden. je nach der Wahl der Diazotierungskomponente können u.a. gelb, orange, rot und braunrot gefärbte Lacke erhalten werden. Beispiel i 15,6 Teile 2-Nitro-i-amino-4-methylbenzol werden wie üblich diazotiert und in sodaalkalischer Lösung mit 15,6 Teilen 5-Pyrazolon-3-carbonsäureäthylester gekuppelt. Der so erhaltene Farbstoff bildet getrocknet ein gelbes Pulver, welches zum Färben der Celluloselacke, wie Zaponlacke, in klaren, lichtechten gelben Tönen sehr gut geeignet ist.As a result of the solubility of these dyes in various organic solvents, they can be used for the production of colored lacquers. Depending on the choice of the diazotization component, varnishes colored, inter alia, yellow, orange, red and brown-red can be obtained. Example i 15.6 parts of 2-nitro-i-amino-4-methylbenzene are diazotized as usual and coupled with 15.6 parts of 5-pyrazolone-3-carboxylic acid ethyl ester in an alkaline soda solution. The dyestuff obtained in this way forms a yellow powder when dried, which is very suitable for coloring cellulose lacquers, such as zapon lacquers, in clear, lightfast yellow tones.

Ähnliche unlösliche, gelbe bis rote Produkte bekommt man mit folgenden Diazotierungsbasen: o-Nitro-p-toluidin, o-, m-, p-Nitranilin, p-Chlor-o-nitranilin usw.Similar insoluble, yellow to red products are obtained with the following Diazotization bases: o-nitro-p-toluidine, o-, m-, p-nitroaniline, p-chloro-o-nitroaniline etc.

Beispiel 2 19,7 Teile Aminoazobenzol werden wie üblich diazotiert. Die filtrierte Diazolösung wird in eine sodaalkalische oder essigsaure Lösung von 15,6 Teilen 5-Pyrazolon-3-carbonsäureäthylester gegossen. Der gebildete Farbstoff wird durch Abnutschen isoliert. Getrocknet bildet er ein orangegelbes Pulver, welches zum Färben von Celluloselacken, wie Zaporilacken usw., verwendet werden kann und diese Materialien in klaren, sehr lichtechten orangen Tönen anfärbt.Example 2 19.7 parts of aminoazobenzene are diazotized as usual. The filtered diazo solution is converted into a soda-alkaline or acetic acid solution of Poured 15.6 parts of 5-pyrazolone-3-carboxylic acid ethyl ester. The dye formed is isolated by suction. When dried it forms an orange-yellow powder, which can be used for dyeing cellulose lacquers, such as zapori lacquers, etc., and colors these materials in clear, very lightfast orange tones.

Durch Verwendung anderer diazotierter Aminoazofarbstoffe, wie z. B. Aminoazotoluol oder die Kupplungsprodukte aus diazotiertem Anilin und -Naphthylamin, diazotiertem p-Chloranilin und m-Amino-p-Icresoläther usw., können mit dem 5-Pyrazolon-3-carbonsäureäthylester orange bis braun gefärbte Lacke erzeugt werden. Beispiel 3 Man löst 4 bis 5 Teile des nach Beispiel 2 erhaltenen Farbstoffes aus diazotiertem p-Aminoazobenzol und 5-Pyrazolon-3-carbonsäureäthylester in iooo Teilen eines f#rägen. Zaponlackes. Die so erhaltene Flüssigkeit, in dünner Schicht auf die verschiedensten Unterlagen (Metalle, Glas, Leder-, Holz, Celluloid, Seide usw.) aufgetragen, hinterläßt beim Eintrocknen einen transparenten Überzug von oranger Farbe. Durch geeignete Zusätze, wie Substrate (Zinkweiß, Bariumsulfat, Gips usw.) oder von unlöslichen Pigmentfarbstoffen, kann der transparente Lack in einen Mattlack oder Decklack übergeführt werden.By using other diazotized aminoazo dyes, such as. B. aminoazotoluene or the coupling products of diazotized aniline and naphthylamine, diazotized p-chloroaniline and m-amino-p-icresol ether, etc., can be produced with the 5-pyrazolone-3-carboxylic acid ethyl ester orange to brown colored paints. EXAMPLE 3 4 to 5 parts of the dye obtained according to Example 2 are dissolved from diazotized p-aminoazobenzene and ethyl 5-pyrazolone-3-carboxylate in 1,000 parts of a dye. Zapon varnishes. The liquid obtained in this way, applied in a thin layer to a wide variety of substrates (metals, glass, leather, wood, celluloid, silk, etc.), leaves behind a transparent coating of orange color when it dries. With suitable additives, such as substrates (zinc white, barium sulfate, gypsum, etc.) or insoluble pigment dyes, the transparent lacquer can be converted into a matt lacquer or top lacquer.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Azofarbstoffen, dadurch gekenn eichnet, daß man Diazoniumverbindungen, welche weder Sulfon- noch Carbonsäuregruppen enthalten und die sich von ehromophore Gruppen enthaltenden primären aromatischen Aminen ableiten, mit 5-Pyrazolon-3-carbonsäureestem kuppelt. PATENT CLAIM: Process for the production of azo dyes, characterized in that diazonium compounds which contain neither sulfonic nor carboxylic acid groups and which are derived from primary aromatic amines containing Ehromophoric groups are coupled with 5-pyrazolone-3-carboxylic acid esters.
DEG73833D 1927-07-26 1928-07-15 Process for the production of azo dyes Expired DE532079C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH532079X 1927-07-26

Publications (1)

Publication Number Publication Date
DE532079C true DE532079C (en) 1931-08-20

Family

ID=4518509

Family Applications (1)

Application Number Title Priority Date Filing Date
DEG73833D Expired DE532079C (en) 1927-07-26 1928-07-15 Process for the production of azo dyes

Country Status (1)

Country Link
DE (1) DE532079C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439798A (en) * 1944-01-21 1948-04-20 Eastman Kodak Co Monoazo compounds containing a pyrazolone nucleus

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439798A (en) * 1944-01-21 1948-04-20 Eastman Kodak Co Monoazo compounds containing a pyrazolone nucleus

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