CH263524A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH263524A
CH263524A CH263524DA CH263524A CH 263524 A CH263524 A CH 263524A CH 263524D A CH263524D A CH 263524DA CH 263524 A CH263524 A CH 263524A
Authority
CH
Switzerland
Prior art keywords
dye
azo dye
preparation
yellow
phosgene
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 CH263524A publication Critical patent/CH263524A/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
    • 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
    • C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde     gefunden,    dass ein wertvoller man je ein     Mol    der beiden     Aminoazofarb-          Azofarbstoff    hergestellt werden kann, wenn Stoffe der Formeln  
EMI0001.0006     
    und  
EMI0001.0007     
    mit Hilfe von     Phosgen    zum     Harnstoffderivat     vereinigt.  



  Der neue Farbstoff stellt in trockenem  Zustand ein gelbbraunes Pulver dar, das sich  in Wasser mit oranger Farbe löst und Baum-    wolle in gelben Tönen färbt. Die Färbungen  zeichnen sich durch gute neutrale und     alka-          lisehe        Ätzbarkeit    aus.  



  Der als     Ausgangsstoff    dienende Farbstoff  der Formel  
EMI0001.0014     
    kann z. B. durch Vereinigen von     diazotierter          1-Aminonaphthalin-4-sulfonsäure    mit     1-Amino-          2-methoxy-5-methylbenzol    in vorzugsweise    Der beim vorliegenden Verfahren eben  falls als Ausgangsstoff dienende Farbstoff  der Formel  
EMI0001.0019     
  
     kann z. B. gemäss dem im Patent Nr. 243602  angegebenen Verfahren hergestellt werden.  



  Die Vereinigung von je einem Molekül  der beiden     Aminoazofarbstoffe    zum Harn-    Stoffderivat mit Hilfe von     Phosgen    kann in  an sich bekannter Weise, z. B. in alkalisch ge  haltenem Medium, vorgenommen werden.      <I>Beispiel:

  </I>  37,1 Teile des durch     Kuppeln    von     diazo-          tierter        1-Aminonaphthalin-4-sulfonsäure        mit          1-Amino-2-methoxy-5-methylbenzol    erhaltenen       Aminoazofarbstoffes-werden    mit 33,7 Teilen       4-Amino    -4' -     oxy-1,

  1'-azobenzol-3'-carbonsäure-          5'-sulfonsäure    unter Zusatz von     Natrium-          carbonat    bis zur deutlich     alkalischen    Reak  tion in 4000 Teilen Wasser gelöst und     unter     Rühren bei 30-35  so lange mit     Phosgen    be-    handelt, bis sich keine freie     NHZ-Gruppe     mehr nachweisen lässt. Das gebildete Harn  stoffderivat wird als     Na-Salz    mit     Hilfe    von       Kochsalz    abgeschieden,     abfiltriert    und ge  trocknet.



  Process for the preparation of an azo dye. It has been found that a valuable one per mole of the two Aminoazofarb-Azo dye can be produced when substances of the formulas
EMI0001.0006
    and
EMI0001.0007
    combined with the help of phosgene to the urea derivative.



  When dry, the new dye is a yellow-brown powder that dissolves in water with an orange color and dyes cotton in yellow tones. The colorations are characterized by their good neutral and alkaline etchability.



  Serving as starting material dye of the formula
EMI0001.0014
    can e.g. B. by combining diazotized 1-aminonaphthalene-4-sulfonic acid with 1-amino-2-methoxy-5-methylbenzene in preferably the dye of the formula also serving as starting material in the present process
EMI0001.0019
  
     can e.g. B. be prepared according to the method specified in Patent No. 243602.



  The combination of one molecule each of the two aminoazo dyes to form the urea derivative with the aid of phosgene can be carried out in a manner known per se, for B. in alkaline ge held medium are made. <I> example:

  </I> 37.1 parts of the aminoazo dye obtained by coupling diazo-tated 1-aminonaphthalene-4-sulfonic acid with 1-amino-2-methoxy-5-methylbenzene-are with 33.7 parts of 4-amino -4 '- oxy-1,

  1'-azobenzene-3'-carboxylic acid-5'-sulfonic acid with the addition of sodium carbonate is dissolved in 4000 parts of water until the reaction is clearly alkaline and treated with phosgene with stirring at 30-35 until it is not free NHZ group can prove more. The urea derivative formed is deposited as sodium salt with the help of common salt, filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man je ein Mol der beiden Aminoazofarbstoffe der Formeln EMI0002.0028 mit Hilfe von Phosgen zum Harnstoffderivat vereinigt. Der neue Farbstoff stellt in trockenem Zustand ein gelbbraunes Pulver dar, das sich in Wasser mit oranger Farbe löst und Baum wolle in gelben Tönen färbt. Die Färbungen zeichnen sich durch gute neutrale und alka lische Ätzbarkeit aus. PATENT CLAIM: Process for the production of an azo dye, characterized in that one mole of each of the two amino azo dyes of the formula EMI0002.0028 combined with the help of phosgene to the urea derivative. When dry, the new dye is a yellow-brown powder that dissolves in water with an orange color and dyes cotton in yellow tones. The colorations are characterized by their good neutral and alkaline etchability.
CH263524D 1947-06-19 1947-06-19 Process for the preparation of an azo dye. CH263524A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH263524T 1947-06-19
CH257720T 1948-10-31

Publications (1)

Publication Number Publication Date
CH263524A true CH263524A (en) 1949-08-31

Family

ID=25730113

Family Applications (1)

Application Number Title Priority Date Filing Date
CH263524D CH263524A (en) 1947-06-19 1947-06-19 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH263524A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2777840A (en) * 1951-05-25 1957-01-15 Ciba Ltd Asymmetrical urea derivatives of monoazo-dyestuffs

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2777840A (en) * 1951-05-25 1957-01-15 Ciba Ltd Asymmetrical urea derivatives of monoazo-dyestuffs

Similar Documents

Publication Publication Date Title
CH238453A (en) Process for the preparation of a copper-compatible polyazo dye.
CH263524A (en) Process for the preparation of an azo dye.
CH263523A (en) Process for the preparation of an azo dye.
CH263522A (en) Process for the preparation of an azo dye.
CH263521A (en) Process for the preparation of an azo dye.
CH263519A (en) Process for the preparation of an azo dye.
CH263520A (en) Process for the preparation of an azo dye.
CH257720A (en) Process for the preparation of an azo dye.
CH198053A (en) Process for the preparation of a polyazo dye.
CH198059A (en) Process for the preparation of a polyazo dye.
CH191165A (en) Process for the preparation of a new monoazo dye.
CH288958A (en) Process for the preparation of a disazo dye.
CH302407A (en) Process for the preparation of a trisazo dye.
CH283761A (en) Process for the preparation of a disazo dye.
CH288957A (en) Process for the preparation of a disazo dye.
CH144489A (en) Process for the preparation of a disazo dye.
CH253649A (en) Process for the preparation of an azo dye.
CH204144A (en) Process for the preparation of a water-soluble disazo dye.
CH302408A (en) Process for the preparation of a trisazo dye.
CH272491A (en) Process for the preparation of an azo dye.
CH204143A (en) Process for the preparation of a water-soluble disazo dye.
CH299605A (en) Process for the preparation of a monoazo dye.
CH277531A (en) Process for the preparation of an optical brightening agent.
CH222993A (en) Process for the preparation of an azo dye.
CH302410A (en) Process for the preparation of a trisazo dye.