CH137654A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH137654A
CH137654A CH137654DA CH137654A CH 137654 A CH137654 A CH 137654A CH 137654D A CH137654D A CH 137654DA CH 137654 A CH137654 A CH 137654A
Authority
CH
Switzerland
Prior art keywords
mol
amino
aniline
copper
oxynaphthalene
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 CH137654A publication Critical patent/CH137654A/en

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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
    • 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
    • C09B45/28—Disazo or polyazo compounds containing copper
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

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

Description

  

  verfahren zur Herstellung eines     Azofarbstoffes.            chlorid,    2 Hol.     2-Amino-5-oxynaphthalin-7-          sulfo@säure    und 1 Hol. Anilin dar.  



  64,8 Teile     des    obigen     tertiären    Konden  sationsproduktes werden in 900 Teilen Was  ser unter Zusatz von 50 Teilen     Natrium-          karbo@nat    gelöst und bei 0 bis 5   eine     Diazo-          lösung    aus 27,4 Teilen     1-Amino-2-benzol-          carbonsäure    zugesetzt.

   Nach vollendeter Kom  bination wird der Farbstoff in üblicher     \Weise     isoliert, .alsdann in 3000 Teilen Wasser an  gerührt und bei 40   mit einer     ammoniaka-          lischen    Lösung von 60     gr    kristallisiertem  Kupfersulfat in 200 Teilen Wasser versetzt.  Man rührt zwei bis drei Stunden und isoliert  das     Ammonsalz    der Kupferverbindung des  Farbstoffes in üblicher Weise.  



  Zum gleichen Produkt gelangt man     selbst-          verständlich#    auch, wenn     man    die Reihenfolge  der beschriebenen     bezw.        erwähnten        Operatio-          rien        :sinngemäss    ändert.    Es wurde gefunden,, dass man einen neuen  metallhaltigen     Azofarbstoff    erhält, wenn man  2 Hol.     2-Amino-5-oxynaphthalin-7-sulfosäure,     2 Mal.     diazotierte        Anthranilsäure,    1 Hol.       Cyanurchlorid,    1 Hol.

   Anilin und kupfer  abgebende Mittel aufeinander einwirken  lässt und diese verschiedenen Operationen  derart vornimmt, dass die Behandlung mit  den kupferabgebenden Mitteln nicht vor der  Kupplungsreaktion vorgenommen und die       Kondensation    mit     Cya,nurchlorid        derart          durchgeführt    wird, dass ,die 2 Hol.     2-Amino-          5-oxyna.phtha.Iin-7-sulfosäure    und das Hol.       Anilin        durch    eine     NH-Gruppe    an den     Tri-          a.zink:ern    gebunden werden.  



  Der neue Farbstoff bildet ein dunkel  rotbraunes Pulver, löst sich in Wasser mit  rotbrauner Farbe und erzeugt auf Baum  wolle oder     Kunstseiden,    wie Viskose- oder       Iiupferoxydamm.oniakseide,.    rotbraune Töne  von vorzüglicher     Liehtechtheit.     



  <I>Beispiel</I>  Man stellt in bekannter Weise das tertiäre       Kondensationsprodukt    aus 1     Mol.    Cyanur-



  process for the production of an azo dye. chloride, 2 hol. 2-Amino-5-oxynaphthalene-7-sulfo @ acid and 1 hol. Aniline.



  64.8 parts of the above tertiary condensation product are dissolved in 900 parts of water with the addition of 50 parts of sodium carbonate and, at 0 to 5, a diazo solution of 27.4 parts of 1-amino-2-benzenecarboxylic acid is added .

   When the combination is complete, the dyestuff is isolated in the usual way, then stirred in 3000 parts of water and, at 40, an ammoniacal solution of 60 g of crystallized copper sulfate in 200 parts of water is added. The mixture is stirred for two to three hours and the ammonium salt of the copper compound of the dye is isolated in the customary manner.



  Of course, you get the same product # if you follow the order of the described or mentioned operations: changes accordingly. It has been found that a new metal-containing azo dye is obtained if you take 2 Hol. 2-Amino-5-oxynaphthalene-7-sulfonic acid, 2 times. diazotized anthranilic acid, 1 hol. Cyanuric chloride, 1 hol.

   Lets aniline and copper donating agent act on each other and carries out these different operations in such a way that the treatment with the copper donating agents is not carried out before the coupling reaction and the condensation with cyano chloride is carried out in such a way that the 2 Hol. 2-Amino-5-oxyna.phtha.Iin-7-sulfonic acid and the hol. Aniline are bound to the tri-zinc by an NH group.



  The new dye forms a dark red-brown powder, dissolves in water with a red-brown color and is produced on cotton or artificial silk, such as viscose or Iupferoxydamm.oniakseide. red-brown tones of excellent light fastness.



  <I> Example </I> The tertiary condensation product is prepared in a known manner from 1 mol. Cyanuric

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen metallhaltigen Azofarbstoffes, dadurch ge- kennzeichnet, dass man 2 Mo1. 2-Amino-5- oxynaphthalin-7-sulfosäure, 2 Mol. diazo- tierte Anthranilsäure, 1 Mol. Cyanurchlorid, 1 Mol. Anilin und kupferabgebende Mittel aufeinander einwirken lässt und diese ver schiedenen Operationen derart vornimmt, PATENT CLAIM: Process for the production of a new metal-containing azo dye, characterized in that 2 Mo1. 2-amino-5-oxynaphthalene-7-sulfonic acid, 2 mol. Diazo- tated anthranilic acid, 1 mol. Cyanuric chloride, 1 mol. Aniline and copper-releasing agents interact and carry out these various operations in such a way that dass die Behandlung mit den kupferabgebenden Mitteln nicht vor der Kupplungsreaktion vorgenommen und die Kondensation mit Cyanurchlorid derart durchgeführt wird, dass die 2 Mol. 2-Amino-5-oxynaphthalin-7-sulfo- säure und das Mol. Anilin durch eine NH- Gruppe an den T'riazinkern gebunden werden. Der neue Farbstoff bildet ein dunkel rotbraunes Pulver, löst sich in Wasser mit rätbrauner Farbe und erzeugt auf Baum wolle oder Kunstseiden rotbraune Töne von vorzüglicher Lichtechtheit. that the treatment with the copper-releasing agents is not carried out before the coupling reaction and the condensation with cyanuric chloride is carried out in such a way that the 2 moles of 2-amino-5-oxynaphthalene-7-sulfonic acid and the mole of aniline are attached by an NH group be bound to the triazine nucleus. The new dye forms a dark red-brown powder, dissolves in water with a raspy-brown color and produces red-brown tones of excellent lightfastness on cotton or artificial silk.
CH137654D 1928-07-14 1928-07-14 Process for the preparation of an azo dye. CH137654A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH137654T 1928-07-14
CH135748T 1928-07-14

Publications (1)

Publication Number Publication Date
CH137654A true CH137654A (en) 1930-01-15

Family

ID=25712562

Family Applications (1)

Application Number Title Priority Date Filing Date
CH137654D CH137654A (en) 1928-07-14 1928-07-14 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH137654A (en)

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