CH279523A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH279523A
CH279523A CH279523DA CH279523A CH 279523 A CH279523 A CH 279523A CH 279523D A CH279523D A CH 279523DA CH 279523 A CH279523 A CH 279523A
Authority
CH
Switzerland
Prior art keywords
azo dye
sulfuric acid
preparation
yellow
acid ester
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 CH279523A publication Critical patent/CH279523A/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
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group

Landscapes

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

Description

  

  Verfahren zur     Herstellung    eines     Azofarbstoffes.       Es     wurde    gefunden, dass     man    zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  den     Leukoschwefelsäureester    der Verbindung  der Formel  
EMI0001.0007     
    mit dianotiertem     1.-Amino-4-methylbenzol    ver  einigt.  



  Der neue Farbstoff bildet ein gelbes Pul  ver, das sich in Wasser leicht     mit    gelber Farbe  löst. und ergibt,     auf    Baumwolle     gedruekt    und  mit     Natriumnitrit    und verdünnter Schwefel  säure     entwickelt,    reine     grünstichig    gelbe Töne  von sehr guten     Echtheitseigenschaften.     



  Der beim vorliegenden     Verfahren    als Aus  gangsstoff dienende     Leukoschwefelsäureester     kann beispielsweise aus dem     Leukoschwefel-          säureester    des     3-Brom-2-aminoanthrachinons     durch Umsetzung mit     Diketen    erhalten wer  den. Die Kupplung mit dem     diazötierten        1-          Amino-4-methylbenzol    kann in üblicher Weise,  z.

   B. in schwach alkalischem,     Natriumcarbonat     enthaltendem Medium bei Temperaturen     zwi-          schen    0  und etwa 25      durehgeführt    werden.       Beispiel:     10,7 Teile     1-Amino-4-methylbenzol    werden.

    in üblicher Weise dianotiert und die Diazo-         lösung    bei 5 bis 8  zu     einer        Lösung    von 58,1       Teilen        Dinatriumsalz    des     Leukoschwefelsäure-          esters    des     3-Brom-2-acetoacetyl-aminoanthra-          chinons    und 30 Teilen     Natriumcarbonat        in     500 Teilen     Wasser        fliessengelassen.    Man  rührt 2 Stunden bei 5 bis 10  und 6 Stunden  bei 10 bis 15 . Der gebildete Farbstoff schei  det sich in Form eines gelben Niederschlages  ab.

   Man saugt ab, wäscht mit verdünnter       Natriumchloridlösung    nach und trocknet im  Vakuum bei 50 bis 60 .



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if the leucosulfuric acid ester of the compound of the formula
EMI0001.0007
    united with dianotated 1.-amino-4-methylbenzene ver.



  The new dye forms a yellow powder that easily dissolves in water with a yellow color. and when printed on cotton and developed with sodium nitrite and dilute sulfuric acid, it produces pure greenish yellow tones with very good fastness properties.



  The leuco-sulfuric acid ester used as starting material in the present process can be obtained, for example, from the leuco-sulfuric acid ester of 3-bromo-2-aminoanthraquinone by reaction with diketene. The coupling with the diazotized 1-amino-4-methylbenzene can be carried out in a conventional manner, for.

   B. in a weakly alkaline medium containing sodium carbonate at temperatures between 0 and approx. Example: 10.7 parts of 1-amino-4-methylbenzene are used.

    dianotized in the usual way and allowed the diazo solution to flow at 5 to 8 to a solution of 58.1 parts of the disodium salt of the leucosulfuric acid ester of 3-bromo-2-acetoacetylaminoanthraquinone and 30 parts of sodium carbonate in 500 parts of water. The mixture is stirred for 2 hours at 5 to 10 and 6 hours at 10 to 15. The dye formed separates out in the form of a yellow precipitate.

   It is filtered off with suction, washed with dilute sodium chloride solution and dried in vacuo at 50 to 60.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man den Leukoschwefelsäureester der Verbindung der Formel EMI0001.0050 mit dianotiertem 1-Amino-4-methylbenzol ver einigt. Der neue Farbstoff bildet ein gelbes Pul ver, das sich in Wasser leicht mit gelber Farbe löst und ergibt, auf Baumwolle gedruckt und mit Natriumnitrit und verdünnter Schwefel säure entwickelt, reine grünstichig gelbe Töne von sehr guten Echtheitseigenschaften. PATENT CLAIM: Process for the production of an azo dye, characterized in that the leuco-sulfuric acid ester of the compound of the formula EMI0001.0050 united with dianotated 1-amino-4-methylbenzene ver. The new dye forms a yellow powder that dissolves easily in water with a yellow color and results, printed on cotton and developed with sodium nitrite and dilute sulfuric acid, pure greenish yellow shades with very good fastness properties.
CH279523D 1950-01-18 1950-01-18 Process for the preparation of an azo dye. CH279523A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH279523T 1950-01-18
CH275436T 1950-01-18

Publications (1)

Publication Number Publication Date
CH279523A true CH279523A (en) 1951-11-30

Family

ID=25731612

Family Applications (1)

Application Number Title Priority Date Filing Date
CH279523D CH279523A (en) 1950-01-18 1950-01-18 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH279523A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820787A (en) * 1954-08-04 1958-01-21 Gen Aniline & Film Corp Anthraquinone azo dye

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820787A (en) * 1954-08-04 1958-01-21 Gen Aniline & Film Corp Anthraquinone azo dye

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