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CH230072A - Process for the preparation of a urea-like disazo dye. - Google Patents

Process for the preparation of a urea-like disazo dye.

Info

Publication number
CH230072A
CH230072A CH230072DA CH230072A CH 230072 A CH230072 A CH 230072A CH 230072D A CH230072D A CH 230072DA CH 230072 A CH230072 A CH 230072A
Authority
CH
Switzerland
Prior art keywords
urea
amino
azobenzene
oxy
weight
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 CH230072A publication Critical patent/CH230072A/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)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     harnstoffartigen        Disazofarbstoffes.       Es wurde gefunden,     dass    man einen neuen       harnstoffartigen        Dis:azofarbstoff    erhält, wenn  man     ein        Mol        4'-(3"-Amino)-benzoylamino-          1,1'-azobenzol-4-oxy-3-ca;

  rbonsäure    -2'-     sulf        on-          säure    mit Hilfe von     Phosgen    mit 1     Mol     4'-     Amino-1,1'-azobenzol-4-oxy-3-carbonsäure     zu einem     asymmetrischen    Harnstoff vereinigt.  



  Der neue Farbstoff stellt ein     gelbbraunes     Pulver dar und färbt Baumwolle in schwach       alkalischem    Bade, das mit einer Kupfersalz  lösung aus Kupfersulfat und weinsaurem       Natrium    versetzt wurde, in waschechten       grünstichiggelben    Tönen an.  



       Beispiel:     33,7     Gewichtsteile    des verseiften     Mono-          azofarbstoffes    aus     diazotierter        1-Amino-4-          acetylaminobenzol-2-sulfonsäure    und     1-Oxy-          benzol-2-earbonsäure    werden als     Na-Salz          -unter    Zusatz von 13,5 Gewichtsteilen Na  triunacetat in 250     Gewichtsteilen    Wasser  gelöst.

   Diese Lösung wird bei etwa 60  mit  <B>1.8.5</B> Gewichtsteilen     3-Nitrobenzoylchlorid,       die mit 5     Gewichtsteilen    Aceton versetzt  wurden, behandelt. Man reduziert das gebil  dete     Nitrobenzoylpro-dukt    mit 42     Gewichts-          teilen        kristallisiertem        Natriumsulfid,    die in  75     Gewichtsteilen    Wasser gelöst wurden, bei  65-70  zum     Aminobenzoylprodukt.     



  45,6 Gewichtsteile des abgeschiedenen       Reduktionsprolduktes    werden mit 25,7 Ge  wichtsteilen     4-Amino-4'-oxy-1,1'-azobenzol-          3'-carbonsäure    unter Zusatz von     Natriumcar-          bonat    bis zur deutlichen     alkalischen        Reaktion     in 3000 Gewichtsteilen Wasser gelöst und  während 20 Stunden unter     Rühren    bei 30 bis  40  mit     Phosgen    behandelt,     bis    sich keine       freie        NH2-Gruppe    mehr nachweisen lässt.

   Das  gebildete     Harnstoffderivat    wird als     Natrium-          salz    gefällt, filtriert und     .getrocknet.  



  Process for producing a urea-like disazo dye. It has been found that a new urea-like dis: azo dye is obtained if one mole of 4 '- (3 "-amino) -benzoylamino-1,1'-azobenzene-4-oxy-3-ca;

  Rboxylic acid -2'-sulfonic acid combined with 1 mol of 4'-amino-1,1'-azobenzene-4-oxy-3-carboxylic acid with the aid of phosgene to form an asymmetric urea.



  The new dye is a yellow-brown powder and dyes cotton in a weakly alkaline bath to which a copper salt solution of copper sulfate and tartrate of sodium has been added in washfast greenish-yellow tones.



       Example: 33.7 parts by weight of the saponified monoazo dye from diazotized 1-amino-4-acetylaminobenzene-2-sulfonic acid and 1-oxybenzene-2-carboxylic acid are triunacetat in the form of the sodium salt - with the addition of 13.5 parts by weight of sodium 250 parts by weight of water dissolved.

   This solution is treated at about 60 with 1.8.5 parts by weight of 3-nitrobenzoyl chloride to which 5 parts by weight of acetone have been added. The nitrobenzoyl product formed is reduced with 42 parts by weight of crystallized sodium sulfide, which were dissolved in 75 parts by weight of water, at 65-70 to the aminobenzoyl product.



  45.6 parts by weight of the precipitated reduction product are dissolved in 3000 parts by weight of water with 25.7 parts by weight of 4-amino-4'-oxy-1,1'-azobenzene-3'-carboxylic acid with the addition of sodium carbonate until a distinctly alkaline reaction and treated with phosgene for 20 hours with stirring at 30 to 40, until no more free NH2 groups can be detected.

   The urea derivative formed is precipitated as sodium salt, filtered and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen harnstoffartigen Disazofarbstoffes, dadurch gekennzeichnet, dass man ein Alol 4'-(3" Amino) -benzoyla.mino-1,1'-azobenzol-4-oxy- 3-carbonsäure-2'-sulfonsäure mit Hilfe von Phosgen mit 1 Mol 4'-Amino-1,1'-azobenzol- 4-oxy-3-carbonsäure zu einem asymmetri schen Harnstoff vereinigt. Claim: Process for the production of a new urea-like disazo dye, characterized in that an Alol 4 '- (3 "amino) -benzoyla.mino-1,1'-azobenzene-4-oxy-3-carboxylic acid-2'-sulfonic acid is used Using phosgene combined with 1 mole of 4'-amino-1,1'-azobenzene-4-oxy-3-carboxylic acid to form an asymmetric urea. Der neue Farbstoff stellt ein gelbbraunes Pulver dar und färbt Baumwolle in schwach alkalisehem Bade, das mit einer Kupfersalz lösung aus Kupfersulfat und weinsaurem Natrium versetzt wurde, in waschechten griinstichiggelben Tönen an. The new dye is a yellow-brown powder and dyes cotton in a weakly alkaline bath to which a copper salt solution of copper sulfate and tartaric acid sodium has been added in washable green-tinged yellow tones.
CH230072D 1942-06-20 1942-06-20 Process for the preparation of a urea-like disazo dye. CH230072A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH230072T 1942-06-20

Publications (1)

Publication Number Publication Date
CH230072A true CH230072A (en) 1943-12-15

Family

ID=4456422

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230072D CH230072A (en) 1942-06-20 1942-06-20 Process for the preparation of a urea-like disazo dye.

Country Status (1)

Country Link
CH (1) CH230072A (en)

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