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
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH212118A publication Critical patent/CH212118A/en

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)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Farbstoffes. dadurch gekennzeichnet, dass man das Pyrazolon der Formel EMI0002.0029 das aus 1-Phenyl-3-methyl-5-pyr-azolorr-4'- carbonsäure und der durch Sulfieren von Dehydrothio-p-toluidin mit Schwefelsäure er hältlichen Sulfosäure hergestellt werden kann, mit diazotierter 2-Amino-l-oxybenzol-4-sul- fonsäure behandelt. Der neue Pyrazolonazofarbstoff stellt ge trocknet ein braunes Pulver dar. PATENT CLAIM: Process for the production of a new dye. characterized in that the pyrazolone of the formula EMI0002.0029 which can be prepared from 1-phenyl-3-methyl-5-pyr-azolorr-4'-carboxylic acid and the sulfonic acid obtainable by sulfating dehydrothio-p-toluidine with sulfuric acid, with diazotized 2-amino-1-oxybenzene-4 -sulfonic acid treated. The new pyrazolone azo dye is a brown powder when dried. Er erzeugt auf der vegetabilen Faser orange Färbungen, die durch Nachkupfern gut licht- und wasch echt werden. It creates orange colorations on the vegetable fibers, which are made lightfast and washfast by re-coppering.
CH212118D 1937-05-22 1937-05-22 Process for the production of a new dye. CH212118A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204242T 1937-05-22
CH212118T 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)

Similar Documents

Publication Publication Date Title
CH212118A (en) Process for the production of a new dye.
CH212117A (en) Process for the production of a new dye.
CH211801A (en) Process for the production of a new dye.
CH204242A (en) Process for the production of a new dye.
CH211800A (en) Process for the production of a new dye.
CH210997A (en) Process for the production of a new dye.
CH128905A (en) Process for the production of a new dye.
CH148005A (en) Process for the preparation of a disazo dye.
CH238518A (en) Process for the production of a new azo dye.
CH177833A (en) Process for the production of a copper-containing dye.
CH200997A (en) Process for the production of a new azo dye.
CH177839A (en) Process for the production of a new azo dye.
CH202248A (en) Process for the preparation of an azo dye.
CH203606A (en) Process for the production of a new azo dye.
CH220751A (en) Process for the production of a new azo dye.
CH223710A (en) Process for the production of a new azo dye.
CH194094A (en) Process for the production of a new azo dye.
CH204443A (en) Process for the production of a new azo dye.
CH238336A (en) Process for the preparation of a new disazo dye.
CH117996A (en) Process for the production of a new dye.
CH229358A (en) Process for the preparation of a trisazo dye.
CH246476A (en) Process for the production of a new azo dye.
CH204445A (en) Process for the production of a new azo dye.
CH99665A (en) Process for the preparation of a black azo dye.
CH204444A (en) Process for the production of a new azo dye.