CH212118A - Process for the production of a new dye. - Google Patents
Process for the production of a new dye.Info
- Publication number
- CH212118A CH212118A CH212118DA CH212118A CH 212118 A CH212118 A CH 212118A CH 212118D A CH212118D A CH 212118DA CH 212118 A CH212118 A CH 212118A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- dye
- new
- pyrazolone
- sulfonic acid
- Prior art date
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Farbstoffes. Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man das Pyrazolon der Formel
EMI0001.0004
das aus 1-Phenyl-3-methyl-5-pyrazolon-4'- carbonsäure und der durch Sulfieren von Dehy- drothio-p-toluidin mit Schwefelsäure erhältli chen Sulfonsäure hergestellt werden kann, mit diazotierter2-Amino-l-oxybenzol-4-sulfon- säure behandelt.
Der neue Pyrazolonazofarbstoff stellt ge trocknet ein braunes Pulver dar. Er erzeugt auf der vegetabilen Faser orange Färbungen, die durch Nachkupfern gut licht- und wasch echt werden. <I>Beispiel:</I> 52,1 Teile des Pyrazolons der Formel
EMI0001.0016
werden in 26 Teilen Natronlauge von<B>36'</B> B@ und 400 Teilen Wasser gelöst. In die fil trierte Lösung gibt man 33 Teile Natronbi- carbonat und etwas Eis und hierauf die Di- azoverbindung aus 18,9 Teilen 2-Amino-l- oxyberrzol-4-sulfonsäure.
Nach beendigter Kupplung wird das Ge misch auf zirka<B>60'</B> aufgewärmt, der teil weise ausgefallene Farbstoff vollends ausge- salzen und nach dem Erkalten abgenutscht.
Das zur Farbstotfherstellung verwendete Pyrazolonderivat kann zum Beispiel durch Kondensation von 4-Nitrobenzol.l.carbonsäure- chlorid mit dem Monosulfierungsprodukt aus Dehydrothioparatoluidin, Reduktion der Nitro- zur Aminogruppe, Hydrazinierung der letz teren nach üblichen Methoden, und Über führung des Hydrazins durch Kondensation mit Acetessigester in das entsprechende 3- Methyl-5-pyrazolori,
oder auch durch Konden sation in Gegenwart eines Phosphorchlorides von 1-Phenyl-3-methyl-5-pyrazolou-4'-carbor)- säure mit dem Monosulfierungsprodukt aus Dehydrothio--p-toluidin erhalten werden.
Process for the production of a new dye. It has been found that a new dye is obtained by using the pyrazolone of the formula
EMI0001.0004
which can be prepared from 1-phenyl-3-methyl-5-pyrazolone-4'-carboxylic acid and the sulfonic acid obtained by sulfating dehydrothio-p-toluidine with sulfuric acid, with diazotized 2-amino-1-oxybenzene-4- sulfonic acid treated.
The new pyrazolonazo dye is a brown powder when dried. It produces orange dyes on the vegetable fibers, which are made lightfast and washfast by re-coppering. <I> Example: </I> 52.1 parts of the pyrazolone of the formula
EMI0001.0016
are dissolved in 26 parts of sodium hydroxide solution of <B> 36 '</B> B @ and 400 parts of water. 33 parts of sodium bicarbonate and a little ice are added to the filtered solution, followed by the diazo compound from 18.9 parts of 2-amino-l-oxyberrzene-4-sulfonic acid.
After the coupling is complete, the mixture is warmed up to about <B> 60 '</B>, the partially precipitated dye is completely salted out and, after cooling, sucked off.
The pyrazolone derivative used for dye production can be obtained, for example, by condensation of 4-Nitrobenzol.l.carbonsäure- chloride with the monosulfation product of dehydrothioparatoluidine, reduction of the nitro to the amino group, hydrazination of the latter by conventional methods, and transfer of the hydrazine by condensation with acetoacetic ester into the corresponding 3-methyl-5-pyrazolori,
or by condensation in the presence of a phosphorus chloride of 1-phenyl-3-methyl-5-pyrazolou-4'-carboric acid with the monosulfation product of dehydrothio - p-toluidine.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH212118T | 1937-05-22 | ||
CH204242T | 1937-05-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH212118A true CH212118A (en) | 1940-10-31 |
Family
ID=25724035
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH212118D CH212118A (en) | 1937-05-22 | 1937-05-22 | Process for the production of a new dye. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH212118A (en) |
-
1937
- 1937-05-22 CH CH212118D patent/CH212118A/en unknown
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