CH212117A - Process for the production of a new dye. - Google Patents

Process for the production of a new dye.

Info

Publication number
CH212117A
CH212117A CH212117DA CH212117A CH 212117 A CH212117 A CH 212117A CH 212117D A CH212117D A CH 212117DA CH 212117 A CH212117 A CH 212117A
Authority
CH
Switzerland
Prior art keywords
pyrazolone
dye
production
new
carboxylic 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 CH212117A publication Critical patent/CH212117A/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)
  • Plural Heterocyclic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Farbstoffes.       Es wurde gefunden, dass man einen neuen Farbstoff erhält, wenn man das     Pyrazolon     der Formel  
EMI0001.0003     
    das aus     1-Phenyl-3-methyl-5-pyrazolon-3'-          carbonsäure    und der durch     Sulfieren    von       Dehydrothio-p-toluidin    mit Schwefelsäure  erhältlichen     Sulfonsäure    hergestellt werden  kann, mit     diazotierter        1-Amino-4-sulfobenzol-          2-carbonsäure    behandelt.

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



       Beispiel:     52,1 Teile des     Pyrazolons    der Formel  
EMI0001.0018     
      werden in 26 Teilen Natronlauge von 36       Be     und 400 Teilen Wasser     gelöst.    In die fil  trierte Lösung gibt man 33 Teile     Natrium-          bicarbonat    und etwas Eis und hierauf die       Diazoverbindung    aus 21,7 Teilen     1-Amino-          4-sulfobenzol-?-carbonsäure.     



  Nach beendigter Kupplung wird das Ge  misch auf etwa 60   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 -1-     earbon-          säurechlorid    mit dem     Monosulfierungspro-          dukt    aus     Dehydrothioparatoluidin,    Reduktion    der     Nitro-    zur     Aminogruppe,        Hydrazinie-          rung    der letzteren nach üblichen Methoden,

    und Überführung des Hydrazins durch Kon  densation mit     Acetessigester    in das entspre  chende 3 -     Methyl    - 5 -     pyrazolon,    oder auch  durch Kondensation in Gegenwart eines  Phosphorchlorids von     1-Phenyl-3-methyl-5-          pyrazolon-3'-carbonsä.ure        mit    dem Mono  sulfierungsprodukt aus     Dehydrothio-p-tolui-          din    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
EMI0001.0003
    which can be prepared from 1-phenyl-3-methyl-5-pyrazolone-3'-carboxylic acid and the sulfonic acid obtainable by sulfating dehydrothio-p-toluidine with sulfuric acid, treated with diazotized 1-amino-4-sulfobenzene-2-carboxylic acid .

      The new pyrazolone azo dye is a brown powder when dried. It creates yellow colorations on the vegetable fibers, which are made lightfast and washfast by re-coppering.



       Example: 52.1 parts of the pyrazolone of the formula
EMI0001.0018
      are dissolved in 26 parts of 36 Be sodium hydroxide solution and 400 parts of water. In the filtered solution are added 33 parts of sodium bicarbonate and a little ice and then the diazo compound from 21.7 parts of 1-amino-4-sulfobenzene -? - carboxylic acid.



  After the coupling is complete, the mixture is warmed up to around 60, the partially precipitated dye is completely salted out and suction filtered after cooling.



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

    and conversion of the hydrazine by condensation with acetoacetic ester in the corresponding 3 - methyl - 5 - pyrazolone, or by condensation in the presence of a phosphorus chloride of 1-phenyl-3-methyl-5-pyrazolone-3'-carboxylic acid with the Monosulfonation product can be obtained from dehydrothio-p-toluidine.

Claims (1)

<B>PATENTAN</B>SPRUCH Verfahren zur Herstellung eines neuen Farbstoffes, dadurch gekennzeichnet, daB man das Pyrazolon der Formel <B><I>1-N</I></B> - ---CONH--f #-C# s# N -CH] SOBH C- C@ l H9 0 das aus 1-Phenyl-3-methyl-5-pyrazolon-3'- carbonsäure und der durch Sulfieren von Dehydrothio-p-toluidin mit Schwefelsäure erhältlichen Sulfonsäure <B> PATENTAN </B> SPRUCH Process for the production of a new dye, characterized in that the pyrazolone of the formula <B><I>1-N</I> </B> - --- CONH - f # -C # s # N -CH] SOBH C- C @ l H9 0 that from 1-phenyl-3-methyl-5-pyrazolone-3'-carboxylic acid and the sulfonic acid obtainable by sulfonating dehydrothio-p-toluidine with sulfuric acid hergestellt werden kann, mit diazotierter 1-Amino-4-sulfobenzol- 2-carbonsäure 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. can be prepared, 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.
CH212117D 1937-05-22 1937-05-22 Process for the production of a new dye. CH212117A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204242T 1937-05-22
CH212117T 1937-05-22

Publications (1)

Publication Number Publication Date
CH212117A true CH212117A (en) 1940-10-31

Family

ID=25724034

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212117D CH212117A (en) 1937-05-22 1937-05-22 Process for the production of a new dye.

Country Status (1)

Country Link
CH (1) CH212117A (en)

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