CH302410A - Process for the preparation of a trisazo dye. - Google Patents

Process for the preparation of a trisazo dye.

Info

Publication number
CH302410A
CH302410A CH302410DA CH302410A CH 302410 A CH302410 A CH 302410A CH 302410D A CH302410D A CH 302410DA CH 302410 A CH302410 A CH 302410A
Authority
CH
Switzerland
Prior art keywords
preparation
parts
trisazo dye
oxynaphthalene
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 CH302410A publication Critical patent/CH302410A/en

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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  
EMI0001.0005     
    worin     N    eine dianotierte     Aminogruppe    bedeu  tet, mit 2 -     Oxynaphthalin    - 6,8 -     disulfonsäure     kuppelt.  



  Der neue Farbstoff bildet ein schwarzes  Pulver, das sich in Wasser leicht löst und     Ve-          lout:sIeder    in     grünstichig    marineblauen Tönen  färbt.  



  Die     Diazoverbindungen    der obigen Formel  können hergestellt werden, indem man     tetrazo-          tiertes        4,4'-Diaminodiphenyl    in saurem Me  dium einseitig mit     1-Amino-8-oxynaphthalin-          3,6-disulfonsäure    kuppelt und die so erhaltene  Verbindung hierauf in alkalischem Medium  mit dianotierter     1-Aminobenzol-4-sulfonsäure     vereinigt.

   Die Kupplung der so erhältlichen       Diazodisazoverbindungen    mit der     2-Oxynaph-          thalin-6,8-disulfonsäure    erfolgt     zweekmässig    in  alkalischem     3ledium.     



  <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 Tei-         len    Wasser, die einen     pH-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  17,3 Teilen 1-     Aminobenzol-4-sulfonsäure    zu  laufen und stürzt unter kräftigem Rühren eine  Lösung von 26 Teilen     Natriumcarbonat    in 120  Teilen Wasser zum Kupplungsgemisch; der     p$-          Wert    soll nicht höher als 8,5 sein.

   Nach 30 Mi  nuten wird eine Lösung aus 30,4 Teilen     2-          Oxyna.phthalin-6,8-disiilfonsäure    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
EMI0001.0005
    wherein N is a dianotated amino group, couples with 2 - oxynaphthalene - 6,8 - disulfonic acid.



  The new dye forms a black powder that dissolves easily in water and velout: it dyes in greenish navy blue tones.



  The diazo compounds of the above formula can be prepared by coupling tetrazolated 4,4'-diaminodiphenyl in acidic medium on one side with 1-amino-8-oxynaphthalene-3,6-disulfonic acid and the compound thus obtained thereupon in an alkaline medium dianotized 1-aminobenzene-4-sulfonic acid combined.

   The coupling of the diazodisazo compounds obtainable in this way with 2-oxynaphthalene-6,8-disulfonic acid takes place in two ways in alkaline 3ledium.



  <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 pH 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, but the mixture should always be clearly acidic to the Congo. After 12 hours, the diazonium solution of 17.3 parts of 1-aminobenzene-4-sulfonic acid is allowed to run at 5 and a solution of 26 parts of sodium carbonate in 120 parts of water is added to the coupling mixture with vigorous stirring; the p $ value should not be higher than 8.5.

   After 30 minutes, a solution of 30.4 parts of 2-Oxyna.phthalin-6,8-disilphonic 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 be deutet, mit 2-Oxynaphthalin-6,8-disulfonsäure kuppelt. Der neue Farbstoff bildet ein schwarzes Pulver, das sich in Wasser leicht löst und Veloursleder in grünstichig marineblauen Tönen färbt. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man die Kupplung in alkalischem Medium durchführt. PATENT 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, couples with 2-oxynaphthalene-6,8-disulfonic acid. The new dye forms a black powder that dissolves easily in water and dyes suede in greenish navy blue tones. SUBCLAIM: Method according to claim, characterized in that the coupling is carried out in an alkaline medium.
CH302410D 1951-06-25 1951-06-25 Process for the preparation of a trisazo dye. CH302410A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH300023T 1951-06-25
CH302410T 1951-06-25

Publications (1)

Publication Number Publication Date
CH302410A true CH302410A (en) 1954-10-15

Family

ID=25734135

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302410D CH302410A (en) 1951-06-25 1951-06-25 Process for the preparation of a trisazo dye.

Country Status (1)

Country Link
CH (1) CH302410A (en)

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