CH211801A - Process for the production of a new dye. - Google Patents

Process for the production of a new dye.

Info

Publication number
CH211801A
CH211801A CH211801DA CH211801A CH 211801 A CH211801 A CH 211801A CH 211801D A CH211801D A CH 211801DA CH 211801 A CH211801 A CH 211801A
Authority
CH
Switzerland
Prior art keywords
production
new
dye
new dye
pyrazolone
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 CH211801A publication Critical patent/CH211801A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (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     
    mit     diazotierter        1-Amino-4-sulfobenzol-2-car-          bonsäure    behandelt.  



  Der neue     Pyrazolonazofarbstoff    stellt ge  trocknet ein braunes Pulver dar. Er erzeugt  auf der     vegetabilen    Faser gelbe Färbungen,    die durch Nachkupfern gut licht- und wasch  echt werden.  



  <I>Beispiel:</I>  52,1 Teile des     Pyrazolons    der Formel  
EMI0001.0011     
           werden    in 26 Teilen Natronlauge von 36   Bö  und 400 Teilen Wasser gelöst. In die fil  trierte Lösung gibt man 33 Teile     Natrium-          bicarbonat    und etwas Fis und hierauf die       Diazoverbindung    aus 21,7 Teilen     1-Amino-          4-sulf        obenzol-2-carbonsäure.     



  Nach beendigter Kupplung wird das Ge  misch auf zirka<B>60'</B>     aufgewärmt,    der teil  weise     ausgefallene    Farbstoff vollends aus  gesalzen und nach dem Erkalten     abgenutscht.     



  Das zur     Farbstoffherstellung        verwendete          Pyrazolonderivat    kann zum Beispiel durch  Kondensation von     3-Nitrobenzol-l-ca.rbon-          säurechlorid    mit dem Dehydrothioparatolui-         din,        Reduktion    der     Nitro-    zur     Aminogruppe,          Hy        drazinierung    der letzteren nach üblichen  Methoden.

   und     Cberführuing    des Hydrazins  durch     Kondensation    mit     Acetessigester    in das  entsprechende     3-hletliyl-5-pyrazolon,    oder  auch durch Kondensation in Gegenwart eines       Phosphorehlorides    von     1-Phenyl-3-meth@-l-5-          pyrazolon-3'-carbonsäure    mit dem     Dehydro-          thio-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
    treated with diazotized 1-amino-4-sulfobenzene-2-carboxylic acid.



  The new pyrazolonazo dye is a brown powder when dried. It produces yellow colorations on the vegetable fiber, which are made lightfast and washfast by re-coppering.



  <I> Example: </I> 52.1 parts of the pyrazolone of the formula
EMI0001.0011
           are dissolved in 26 parts of sodium hydroxide solution of 36 Bo and 400 parts of water. 33 parts of sodium bicarbonate and a little Fis and then the diazo compound from 21.7 parts of 1-amino-4-sulfobenzene-2-carboxylic acid are added to the filtered solution.



  After the coupling is complete, the mixture is warmed up to about <B> 60 '</B>, the partially precipitated dye is completely salted out and suction filtered after cooling.



  The pyrazolone derivative used to produce the dyestuff can be produced, for example, by condensation of 3-nitrobenzene-1-carbonic acid chloride with dehydrothioparatoluidine, reduction of the nitro to the amino group, and hydrazination of the latter by customary methods.

   and Conversion of the hydrazine by condensation with acetoacetic ester into the corresponding 3-halyl-5-pyrazolone, or by condensation in the presence of a phosphorus chloride of 1-phenyl-3-meth @ -l-5-pyrazolone-3'-carboxylic acid with the dehydro - thio-p-toluidine can be obtained.

Claims (1)

PATENTANSPRUCH: Zerfahren zur Herstellung eines neuen Farbstoffe, dadurch gekennzeichnet, dass man das Py razolon der Formel EMI0002.0035 mit diazotierter 1-Amino-4-sulfobenzol-?-car- bonsäure behandelt. Der neue Pyrazolonazofarbstoff stellt ge trocknet ein braunes Pulver dar. Er erzeugt auf der vegetabilen Faser gelbe Färbungen die durch Nachkupfern gut licht- und wasch echt werden. PATENT CLAIM: Process for the preparation of a new dyestuff, characterized in that the Py razolon of the formula EMI0002.0035 treated with diazotized 1-amino-4-sulfobenzene -? - carboxylic acid. The new pyrazolonazo dye is a brown powder when dried. It produces yellow colorations on the vegetable fibers which are made lightfast and washfast by re-coppering.
CH211801D 1937-05-22 1937-05-22 Process for the production of a new dye. CH211801A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204242T 1937-05-22
CH211801T 1937-05-22

Publications (1)

Publication Number Publication Date
CH211801A true CH211801A (en) 1940-10-15

Family

ID=25724033

Family Applications (1)

Application Number Title Priority Date Filing Date
CH211801D CH211801A (en) 1937-05-22 1937-05-22 Process for the production of a new dye.

Country Status (1)

Country Link
CH (1) CH211801A (en)

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