CH220648A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

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Publication number
CH220648A
CH220648A CH220648DA CH220648A CH 220648 A CH220648 A CH 220648A CH 220648D A CH220648D A CH 220648DA CH 220648 A CH220648 A CH 220648A
Authority
CH
Switzerland
Prior art keywords
mol
product
weight
parts
amino
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 CH220648A publication Critical patent/CH220648A/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
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16Preparation 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 neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    erhält, wenn man 1     Mol        Cyanur-          ehlorid,    1     Mol    des Produktes, das erhalten  wird durch Reduzieren des     Acylierungspro-          duktes    aus 1     Mol        m-Nitrobenzoylchlorid    und  1     Mol    des     Umsetzungsproduktes        aus    1     Mol          4,

  4'-Diaminodiphenyl-3-sulfonsäure    und 1     Mol          1-Amino-4-bromanthraehino@n-2-sulfonsäure,     1     Mol        4-Amino-4'-ogy-1,1'-azobenzol-3'-car-          bonsäure,    und 1     Mol    Anilin aufeinander ein  wirken lässt. Der neue Farbstoff stellt ein  dunkles Pulver dar, das sich in Wasser mit  grüner Farbe löst und Baumwolle in       schwach    alkalischem Bade in Gegenwart von  Kupfersulfat und weinsaurem Natrium in       wasch-    und lichtechten grünen Tönen färbt.

         Beispiel:     56,4     Gewichtsteile    des     Umsetzungspro-          duktes    aus 1     Mol        4,4'-Diaminodiphenyl-3-          sulfonsäure    und 1     Mol        1-Amino-4-b@rom-          anthrachinon-2-sulfonsäure    werden als     Di-          natriums@alz    in 2000     Gewichtsteilen    Wasser    unter Zusatz von 8,4 Gewichtsteilen     Na-          triumbicarbonat    .gelöst.

       Diese    Lösung wird  bei zirka 60   mit 18,5     Gewichtsteilen        meta-          Nitrobenzoylchlorid,    die mit 1,0 Gewichts  teilen Aceton versetzt wurden, behandelt.  Man     reduziert    das     entstandene        Nitrobenzoyl-          produkt    mit 42     Gewiehtsteilen    kristallisier  tem     Natriumsulfid,    die in     10'0        Gewichtsteilen     Wasser gelöst wurden,

   bei     60-70'    zum     ent-          sprechenden        Aminobenzoylprodukt.    68;3 Ge  wichtsteile des abgeschiedenen Reduktions  produkte-, werden als neutrale Lösung in  1000     Gewichtsteilen        Wasser    zu einer     An-          schlämmung    von 18,5     Gewichtsteilen        Cyanur-          chlorid    in 500 Gewichtsteilen kaltem     Wasser     gegeben.

   Man hält .die Temperatur     1Stunde     bei<B>10-15'.</B> Die bei der Kondensation ent  stehende .Salzsäure wird durch die entspre  chende Menge     Natriumcarbonat    neutrali  siert. Hernach werden 25,7 Gewichtsteile  4     -Amino    -     4'-ogy-1,1'-azobenzol-3'-carbonsäure     in 1000 Gewichtsteilen     warmem    Wasser ge  löst, zum     Monokondensationsprodukt    gegeben.      Die Temperatur wird dabei auf     40'    erhöht.  Nach 48 Stunden gibt man 18 Gewichtsteile  Anilin zu und hält .die Temperatur während  der bleichen     Zeit    auf 80  .

   Das tertiäre Kon  densationsprodukt ist nach dieser     Zeit        bebil-          det.    Es wird mit     Natriumehlorid        abbeschie-          den    und getrocknet.



  Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mol of cyanuric chloride, 1 mol of the product obtained by reducing the acylation product from 1 mol of m-nitrobenzoyl chloride and 1 mol of the reaction product from 1 mol of 4,

  4'-diaminodiphenyl-3-sulfonic acid and 1 mole of 1-amino-4-bromanthraehino @ n-2-sulfonic acid, 1 mole of 4-amino-4'-ogy-1,1'-azobenzene-3'-carboxylic acid, and 1 mole of aniline interacts. The new dye is a dark powder that dissolves in water with a green color and colors cotton in a weakly alkaline bath in the presence of copper sulfate and tartrate of sodium in washable and lightfast green tones.

         Example: 56.4 parts by weight of the reaction product from 1 mol of 4,4'-diaminodiphenyl-3-sulfonic acid and 1 mol of 1-amino-4-b @ romanthraquinone-2-sulfonic acid are sold as disodium @ alz in 2000 Parts by weight of water with the addition of 8.4 parts by weight of sodium bicarbonate .gelöst.

       This solution is treated at about 60 with 18.5 parts by weight of meta-nitrobenzoyl chloride to which 1.0 part by weight of acetone has been treated. The nitrobenzoyl product formed is reduced with 42 parts by weight of crystallized sodium sulfide, which was dissolved in 10 parts by weight of water,

   at 60-70 'to the corresponding aminobenzoyl product. 68; 3 parts by weight of the separated reduction products are added as a neutral solution in 1000 parts by weight of water to a suspension of 18.5 parts by weight of cyanuric chloride in 500 parts by weight of cold water.

   The temperature is kept at <B> 10-15 'for 1 hour. </B> The hydrochloric acid formed during the condensation is neutralized by the appropriate amount of sodium carbonate. Thereafter, 25.7 parts by weight of 4-amino-4'-ogy-1,1'-azobenzene-3'-carboxylic acid dissolved in 1000 parts by weight of warm water, added to the monocondensation product. The temperature is increased to 40 '. After 48 hours, 18 parts by weight of aniline are added and the temperature is kept at 80 during the bleaching time.

   The tertiary condensation product is formed after this time. It is coated with sodium chloride and dried.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man 1 Mol Cyanurchlorid, 1 Hol des Pro duktes, dass erhalten wird durch Reduzieren des Acylierunbsproduktes aus 1 Mol m-Nitro- benzoylchlori.d und 1 Mol des Umsetzungs produktes aus 1 Mol 4, PATENT CLAIM: Process for the preparation of a new azo dye, characterized in that 1 mol of cyanuric chloride, 1 hol of the product that is obtained by reducing the acylation product from 1 mol of m-nitrobenzoylchlori.d and 1 mol of the reaction product from 1 mol 4, 4'-Diaminodiphenyl-3- sulfonsäure und 1 Mol 1-Amino-4-brom- a.nthrachinon-2-sulfonsä.ure,1 Mo14- Amino-4'- oxy-1,1'-azobenzol-3'-carbonsäure, und 1 Mol Anilin aufeinander einwirken lässt. Der neue Farbstoff stellt ein dunkles Pulver dar, das sich in Wasser mit grüner Farbe löst und Baumwolle in sehwach alkalischem Bade in Clegenwart von Kupfersulfat; und wein saurem Natrium in wasch- und lichtechten grünen Tönen färbt. 4'-diaminodiphenyl-3-sulfonic acid and 1 mole of 1-amino-4-bromo-a.nthraquinone-2-sulfonic acid, 1 Mo14-amino-4'-oxy-1,1'-azobenzene-3'-carboxylic acid , and let 1 mole of aniline act on each other. The new dye is a dark powder that dissolves in water with a green color, and cotton in a weakly alkaline bath in copper sulphate; and wine acid sodium colors in washable and lightfast green tones.
CH220648D 1940-07-09 1940-07-09 Process for the production of a new azo dye. CH220648A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH220648T 1940-07-09
CH217241T 1940-07-09

Publications (1)

Publication Number Publication Date
CH220648A true CH220648A (en) 1942-04-15

Family

ID=25725991

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220648D CH220648A (en) 1940-07-09 1940-07-09 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH220648A (en)

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