CH87889A - Process for the preparation of a related disazo dye. - Google Patents

Process for the preparation of a related disazo dye.

Info

Publication number
CH87889A
CH87889A CH87889DA CH87889A CH 87889 A CH87889 A CH 87889A CH 87889D A CH87889D A CH 87889DA CH 87889 A CH87889 A CH 87889A
Authority
CH
Switzerland
Prior art keywords
orange
disazo dye
yellow
dye
parts
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 CH87889A publication Critical patent/CH87889A/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
    • 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
    • C09B31/143—1,2-Diazoles
    • C09B31/147—Pyrazoles
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds
    • C09B45/26—Disazo or polyazo compounds containing chromium
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
    • C09B45/40—Chromium compounds

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     beizenziehenden        Disazofarbstoffes.       Es wurde gefunden, dass durch Kuppeln  von     diazotierter        m-Aininobenzoesäure    mit der       N-Methyl-co-sulfosäure    der     m-Aininobenzoe-          säure,    Abspalten des     N-Methyl-io-sulfosäure-          restes,        Weiterdiazotieren    der so erhaltenen       Aminoazobenzoldicarbonsäure    und Kuppeln  mit     1-(4'-oxy-5'-carboxy-)

  phenyl-3-methylpyra-          zolon    ein neuer     Disazofarbstoff    erhalten wird.  Dieser     Disazofarbstoff,    welcher ein orange  rotes Pulver bildet, löst sich in Wasser mit  orangegelber, in     konzentrierter        Schwefelsäure     mit roter Farbe und gibt auf Baumwolle,     niit     Hilfe von Chromacetat gedruckt, gelborange  Färbungen von hervorragender Licht-,     Chlor-          und    Seifenechtheit.  



  <I>Beispiel:</I>  13,7 Teile     m-Aminobenzoesäure        werden     in 100 Teilen Wasser und 4,0 'feilen     NaOH     gelöst und mit der molekularen Menge     Fornial-          dehydbisulfitlösung        aus    3,0 Teilen Formal  dehyd und 10,4 Teilen     NaHS03    kondensiert  durch achtstündiges Erwärmen auf 40-50'.

    Die erhaltene     Lösung    der     Methyl-m-Sulfover-          bindung    aus     m-Aminobenzoesäure    wird bei  Gegenwart von     Natriumacetat    vereinigt mit    der auf übliche Weise erhaltenen     Diazover-          bindung    aus<B>13,7</B> Teilen     m-Aniinobenzoe-          säure.    Nach mehrtägigem     Rühren    bei Eis  temperatur verschwindet die     Diazoverbindung     unter     Ausscheidung    eines     orangegelben        Farb-          stoffes,

      der durch     Aussalzen    isoliert wird.  Die     @Ietliy        1-(o-Salfogruppe    wird hierauf auf  bekannte Weise abgespalten,     zuin    Beispiel  durch     viertelstündiges    Kochen mit     500    Teilen       2 'o        Na011.    Die nunmehr gebildete     4-r@mino-          azobenzol-2,3'-dicarbonsiiure    wird nun durch       Ansäuren    mit Essigsäure und     Aussalzen    -iso  liert und stellt ein Hellgelbes Pulver dar,

   das  in 250 Teilen     Wasser    und 8 Teilen     Na0H          neuerdings    gelöst wird. Die tief orangegelbe  Lösung wird     finit   <B>6,9</B> Teilen     NaNOs    versetzt  und durch plötzliches     Ansäuren    mit Salz  säure unter Eiszugabe     diazotiert    und mit der       soloalkalischen        Lösung    aus     23,-1    Teilen     1-          (4'-oxy-5'-earboxy-)        phenyl-I-inethylpyrazoloii          kombiniert.  



  Process for the preparation of a related disazo dye. It has been found that by coupling diazotized m-amino benzoic acid with the N-methyl-co-sulfonic acid of m-amino benzoic acid, splitting off the N-methyl-io-sulfonic acid residue, further diazotizing the aminoazobenzenedicarboxylic acid thus obtained and coupling with 1- (4'-oxy-5'-carboxy-)

  phenyl-3-methylpyrazolone a new disazo dye is obtained. This disazo dye, which forms an orange-red powder, dissolves in water with an orange-yellow color and in concentrated sulfuric acid with a red color and, printed with the help of chromium acetate, gives yellow-orange colorations of excellent light, chlorine and soap fastness.



  <I> Example: </I> 13.7 parts of m-aminobenzoic acid are dissolved in 100 parts of water and 4.0 parts of NaOH, and with the molecular amount of formaldehyde bisulfite solution of 3.0 parts of formaldehyde and 10.4 parts of NaHSO3 condensed by heating to 40-50 'for eight hours.

    The resulting solution of the methyl-m-sulfo compound from m-aminobenzoic acid is combined in the presence of sodium acetate with the diazo compound obtained in the customary manner from 13.7 parts of m-aniinobenzoic acid. After several days of stirring at ice temperature, the diazo compound disappears with the excretion of an orange-yellow dye,

      which is isolated by salting out. The @Ietliy 1- (o-salfo group is then split off in a known manner, for example by boiling for 15 minutes with 500 parts of 2 'o Na011 -isolated with acetic acid and salting out and is a light yellow powder,

   which has recently been dissolved in 250 parts of water and 8 parts of NaOH. The deep orange-yellow solution is finitely <B> 6.9 </B> parts of NaNOs and diazotized by sudden acidification with hydrochloric acid with the addition of ice and mixed with the solo alkaline solution of 23.1 parts of 1- (4'-oxy-5 ' -earboxy-) phenyl-I-inethylpyrazoloii combined.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines beizen ziehenden Disazofarbstoffes, dadurch gekenn- zeichnet, dass man dianotierte m-Aminoben- zoe -ihre mit der N-21ethyl-u)-sulfosäui,e der iri--zlrninobenzoesiiui@e kuppelt, dah man hier auf den ', PATENT CLAIM: A process for the production of a pickling disazo dye, characterized in that dianotated m-aminobenzoes -yours are coupled with the N-21ethyl-u) -sulfosäui, e of the iri-zlrninobenzoesiiui @ e the ', \-Metlivl-co-sulfosäui-eiest des erhal tenen ILIonoazofarbstoffes abspaltet ruid die so erhaltene Amirioazoberrzoldicai-borisäure weiter dianotiert und. mit 1-(4'-oxy-5'-eai@boxy-) phenvl-3-metli@-Ipj-razolon kuppelt. Der so er haltene Disazofarbstoff bildet ein orangerotes Pulver. \ -Metlivl-co-sulfosäui-eiest of the obtained IL-ionazo dye splits off ruid the amirioazoberrzoldicai-boric acid further dianotized and. with 1- (4'-oxy-5'-eai @ boxy-) phenvl-3-metli @ -Ipj-razolon. The disazo dye obtained in this way forms an orange-red powder. Bist sich in Wasser mit orangegelber und in konzentrierter Schivefcls@iure mit roter Farbe und gibt auf Baumwolle, reit Hilfe voll C,'hrornaeetat -edruckt, gelborange Fiir- burigen von hervorragender Licht-. Chlor- und Seifenechtheit. If you are in water with orange-yellow and in concentrated Schivefcls @ iure with red color and give up on cotton, rides aid full of C, hornate-printed, yellow-orange filaments of excellent light. Chlorine and soap fastness.
CH87889D 1917-10-03 1917-10-03 Process for the preparation of a related disazo dye. CH87889A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH55711T 1917-10-03
CH87889T 1917-10-03

Publications (1)

Publication Number Publication Date
CH87889A true CH87889A (en) 1921-01-03

Family

ID=25698009

Family Applications (1)

Application Number Title Priority Date Filing Date
CH87889D CH87889A (en) 1917-10-03 1917-10-03 Process for the preparation of a related disazo dye.

Country Status (1)

Country Link
CH (1) CH87889A (en)

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