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CH302411A - Process for the preparation of a trisazo dye. - Google Patents

Process for the preparation of a trisazo dye.

Info

Publication number
CH302411A
CH302411A CH302411DA CH302411A CH 302411 A CH302411 A CH 302411A CH 302411D A CH302411D A CH 302411DA CH 302411 A CH302411 A CH 302411A
Authority
CH
Switzerland
Prior art keywords
preparation
parts
oxynaphthalene
trisazo dye
coupling
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH302411A publication Critical patent/CH302411A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/38Trisazo dyes ot the type
    • C09B35/44Trisazo dyes ot the type the component K being a hydroxy amine
    • C09B35/46Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
    • C09B35/463D being derived from diaminodiphenyl

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Coloring (AREA)

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 300023.    Verfahren zur     Herstellung    eines     Trisazofarbstoffes.       Es wurde gefunden, dass man zu einem     wertvollen        Trisazofarbstoff    gelangt, wenn man  eine     Diazoverbindung    der Formel  
EMI0001.0006     
    worin<B>X</B> eine     diazotierte        Aminogruppe    be  deutet, mit 1-     Oxynaphthalin    - 4 -     sulfonsäure     kuppelt.  



  Der neue Farbstoff bildet ein schwarzes  Pulver, das sieh in Wasser leicht löst und  chromgegerbtes Leder, insbesondere     Velours-          lecler,    in vollen marineblauen Tönen färbt.  



  Die     Diazoverbindungen    der obigen Formel  können hergestellt werden, indem man     tetrazo-          tiertes4,4'-Diaminodiphenyl    in saurem Medium  einseitig mit     1-Amino-8-oxynaphthalin-3,6-di-          Sulfonsäure    kuppelt und die so erhaltene     Ver-          bindunc    hierauf in alkalischem Medium mit  dianotierter     1-Aminobenzol-2,5-disulfonsäure     vereinigt.

   Die     Kupplung    der so erhältlichen       1)iazodisazoverbindungen    mit der     1-0xynaph-          thalin-4-sulfonsäure        erfolgt    zweckmässig in  alkalischem     Medhtm.     



  <I>Beispiel:</I>  Man     tetrazotiert    19 Teile     4,4'-Diamino-          diphenyl    in bekannter Weise. Zu dieser       Tetrazolösung    tropft man innert 1 Stunde eine  klare Lösung von 34,1 Teilen     1-Amino-8-          oxynaphthalin-3,6-disulfonsäure    in 300 Teilen    Wasser, die einen     pil-Wert    von 5,6 zeigt. Die  Temperatur beträgt 10 bis 15 .

   Durch all  mähliches     Zutropfen    einer verdünnten,     wäss-          rigen    Lösung von     Natriumcarbonat    stumpft  man die bei der Kupplung freiwerdende Mi  neralsäure ab; das Gemisch soll aber immer  deutlich kongosauer reagieren. Nach 12 Stun  den lässt man bei 5  die     Diazoniumlösung    aus  25,3 Teilen     1-Aminobenzol-2,5-disulfonsäure     zulaufen und stürzt unter kräftigem Rühren  eine Lösung von 26 Teilen     Natriumearbonat    in  120 Teilen Wasser zum Kupplungsgemisch;  der     pH-Wert    soll nicht höher als 8,5 sein.

   Nach  30 Minuten wird eine Lösung aus 22,4 Teilen       1-Oxynaphthalin-4-sulfonsäure    und 5 Teilen       Natriumcarbonat    in 150 Teilen Wasser zuge  geben. Nach zweistündigem Rühren wird  durch Zugabe von Salzsäure das Reaktions  gemisch schwach sauer gestellt, der abgeschie  dene Farbstoff     abfiltriert    und     getrocknet.  



  <B> Additional patent </B> to main patent no. 300023. Process for the production of a trisazo dye. It has been found that a valuable trisazo dye is obtained by using a diazo compound of the formula
EMI0001.0006
    wherein <B> X </B> denotes a diazotized amino group, with 1-oxynaphthalene-4-sulfonic acid couples.



  The new dye forms a black powder that dissolves easily in water and colors chrome-tanned leather, especially suede lecler, in full navy blue tones.



  The diazo compounds of the above formula can be prepared by coupling tetrazoated4,4'-diaminodiphenyl in an acidic medium on one side with 1-amino-8-oxynaphthalene-3,6-disulphonic acid and then coupling the resulting compound in an alkaline medium Medium combined with dianotized 1-aminobenzene-2,5-disulfonic acid.

   The coupling of the 1) iazodisazo compounds thus obtainable with 1-oxynaphthalene-4-sulfonic acid is expediently carried out in an alkaline medium.



  <I> Example: </I> 19 parts of 4,4'-diaminodiphenyl are tetrazotized in a known manner. A clear solution of 34.1 parts of 1-amino-8-oxynaphthalene-3,6-disulfonic acid in 300 parts of water, which has a pil value of 5.6, is added dropwise to this tetrazo solution over a period of 1 hour. The temperature is 10 to 15.

   Gradual dropwise addition of a dilute, aqueous solution of sodium carbonate blunted the mineral acid released during the coupling; the mixture should always react clearly acidic to the Congo. After 12 hours, the diazonium solution of 25.3 parts of 1-aminobenzene-2,5-disulfonic acid is allowed to run in at 5 and, with vigorous stirring, a solution of 26 parts of sodium carbonate in 120 parts of water forms the coupling mixture; the pH should not be higher than 8.5.

   After 30 minutes, a solution of 22.4 parts of 1-oxynaphthalene-4-sulfonic acid and 5 parts of sodium carbonate in 150 parts of water is added. After two hours of stirring, the reaction mixture is made weakly acidic by adding hydrochloric acid, and the dyestuff deposited is filtered off and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Trisazo- farbstoffes, dadurch gekennzeichnet, dass man eine Diazoverbindung der Formel EMI0002.0001 worin X eine diazotierte Aminogruppe bedeu tet, mit 1-Oxynaphthalin-4-sulfonsäure kup pelt. Der neue Farbstoff bildet ein schwarzes Pulver, das sich in Wasser leicht löst und chromgegerbtes Leder, insbesondere Velours leder, in vollen marineblauen Tönen färbt. Claim: Process for the preparation of a trisazo dye, characterized in that a diazo compound of the formula EMI0002.0001 wherein X is a diazotized amino group, with 1-oxynaphthalene-4-sulfonic acid kup pelt. The new dye forms a black powder that dissolves easily in water and colors chrome-tanned leather, especially suede, in full navy blue tones. ZTNTERANSPRUC11 Verfahren gemäss Patentanspruch, dadurch gekennzeiehnet, dass man die Kupplung in alkalischem Medium durehfülirt. ZTNTERANSPRUC11 Method according to patent claim, characterized in that the coupling is carried out in an alkaline medium.
CH302411D 1951-06-25 1952-02-21 Process for the preparation of a trisazo dye. CH302411A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH300023T 1951-06-25
CH302411T 1952-02-21

Publications (1)

Publication Number Publication Date
CH302411A true CH302411A (en) 1954-10-15

Family

ID=25734136

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302411D CH302411A (en) 1951-06-25 1952-02-21 Process for the preparation of a trisazo dye.

Country Status (1)

Country Link
CH (1) CH302411A (en)

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