CH304721A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH304721A
CH304721A CH304721DA CH304721A CH 304721 A CH304721 A CH 304721A CH 304721D A CH304721D A CH 304721DA CH 304721 A CH304721 A CH 304721A
Authority
CH
Switzerland
Prior art keywords
azo dye
oxy
aminopyrimidine
preparation
dyes
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Farbe Bayer
Original Assignee
Bayer Ag
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 Bayer Ag filed Critical Bayer Ag
Publication of CH304721A publication Critical patent/CH304721A/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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom

Description

  

  Verfahren zur Herstellung     eines        Azofarbstofes:       Es wurde gefunden, dass man neue wert  volle     Azofarbstoffe    erhält, wenn man     Diazo-          v        erbindungen    der Benzol- oder     Naphthalin-          reihe    oder     Tetrazoverbindlmgen    mit Abkömm  lingen des     4-Oxy-6-aminopyrimidins        kuppelt     und die so erhältlichen     Azofarbstoffe    gege  benenfalls in ihre     Metallkomplexverbindungen     überführt.

   Als derartige Abkömmlinge des       4-Oxy-6-aminopyrimidins    kommen beispiels  weise in Frage:     2,4-Dioxy-6-aminopyrimidin,          3-Phenyl-2,4-dioxy-6-aminopyrimidin,        3-Me-          thyl    - 2,4 -     dioxy    - 6 -     aminopyrimidin,    2     -Thiol-4-          oxy-6-aminopyrimidin,        3-Phenyl-2-thiol-4-oxy-          6    -     aminopyrimidin,

      4 -     Oxy-    6 -     amino    - 2 -     cyan-          aminopyrimidin.     



  Je nachdem, ob die verwendeten     Diazokom-          ponenten        Sulfonsäuregruppen        und/oder        Carb-          oxylgruppen    enthalten oder nicht, eignen sich  die erhaltenen Farbstoffe zum Färben von  Wolle, Baumwolle, Viskose, Kunstseide und  Papier oder als Pigmentfarbstoffe. Die neuen  Farbstoffe ergeben auf den genannten Faser  materialien volle klare gelbe Töne. von guter       Alkali-    und Säureechtheit.

   Obwohl die Kupp  lungsfähigkeit der     Barbitursäure    bekannt ist,  war es nicht ohne weiteres vorauszusehen, dass  auch ihre     Stickstoffabkömmlinge        kuppeln        lind     Farbstoffe von den     genannten    Eigenschaften  liefern     würden.     



  Gegenstand dieses Patentes ist nun ein  Verfahren zur Herstellung eines neuen     Mono-          azofarbstoffes.    Das Verfahren besteht darin,  dass man     diazotierte        1-Aminobenzol-2-carbon-          sällre-4-snlfonsäure    mit 4-Oxy-6-amino-2-cyan-         aminopyrimidin    kuppelt. Der so hergestellte       Monoazofarbstoff    ist     ein    gelbes Pulver, wel  ches aus wässriger Lösung Papier in sehr kla  ren,     lichtechten        grünstichig    gelben Tönen  färbt.

           Beispiel:     21,7g (=     1/1o        Mol)        1-Aminobenzol-2-.car-          bonsäure-4-sulfonsäure    werden in 200     cm3     Eiswasser mit 25     eins    technischer Salzsäure  angerührt und mit 6,9g     Natriumnitrit        diazo-          tiert.    Die     Diazoverbindung        läuft    zu einer Lö  sung von 15,2 g (=     111o        Mol)

          4-Oxy-6-amino-          2-cyanaminopyrimidin    in 500     cm3    Wasser  und 30 g Soda. Der mit Kochsalz     ausge'salzene,     isolierte und getrocknete     Monoazofarbstoff    ist  ein gelbes Pulver, welches aus wässriger Lö  sung Papier in sehr klaren, lichtechten grün  stichig gelben Tönen färbt.



  Process for the preparation of an azo dye: It has been found that new valuable azo dyes are obtained if diazo compounds of the benzene or naphthalene series or tetrazo compounds with derivatives of 4-oxy-6-aminopyrimidine are coupled and the azo dyes obtainable in this way possibly converted into their metal complex compounds.

   Examples of such derivatives of 4-oxy-6-aminopyrimidine are: 2,4-dioxy-6-aminopyrimidine, 3-phenyl-2,4-dioxy-6-aminopyrimidine, 3-methyl-2,4 - dioxy - 6 - aminopyrimidine, 2-thiol-4-oxy-6-aminopyrimidine, 3-phenyl-2-thiol-4-oxy- 6 - aminopyrimidine,

      4-oxy-6-amino-2-cyano-aminopyrimidine.



  Depending on whether or not the diazo components used contain sulfonic acid groups and / or carbonyl groups, the dyes obtained are suitable for dyeing wool, cotton, viscose, rayon and paper or as pigment dyes. The new dyes produce full, clear yellow tones on the fiber materials mentioned. of good alkali and acid fastness.

   Although the coupling ability of barbituric acid is known, it was not easy to foresee that its nitrogen derivatives would also couple and produce dyes with the properties mentioned.



  The subject of this patent is a process for the production of a new monoazo dye. The process consists in coupling diazotized 1-aminobenzene-2-carbo-sallre-4-sulfonic acid with 4-oxy-6-amino-2-cyano-aminopyrimidine. The monoazo dye produced in this way is a yellow powder which, from aqueous solution, colors paper in very clear, lightfast greenish yellow tones.

           Example: 21.7 g (= 1/10 mol) of 1-aminobenzene-2-carboxylic acid-4-sulfonic acid are stirred into 200 cm3 of ice water with technical grade hydrochloric acid and diazotized with 6.9 g of sodium nitrite. The diazo compound leads to a solution of 15.2 g (= 111o mol)

          4-Oxy-6-amino-2-cyanaminopyrimidine in 500 cm3 of water and 30 g of soda. The isolated and dried monoazo dye is salted out with common salt and is a yellow powder which, from aqueous solution, colors paper in very clear, lightfast green, yellowish tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man diazotierte 1-Aminobenzol-2-earbonsäure- 4-sulfonsäure mit 4-Oxy-6-amino-2-cyanamino- pyrimidin kuppelt. Der neue Azofarbstoff ist ein gelbes Pul ver, welches @ aus wässriger Lösung Papier in sehr klaren, lichtechten grünstichig gelben Tönen färbt. PATENT CLAIM: Process for the production of a new azo dye, characterized in that diazotized 1-aminobenzene-2-carboxylic acid-4-sulfonic acid is coupled with 4-oxy-6-amino-2-cyanamino-pyrimidine. The new azo dye is a yellow powder which @ dyes paper in very clear, lightfast greenish yellow tones from an aqueous solution.
CH304721D 1951-05-07 1952-04-28 Process for the preparation of an azo dye. CH304721A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE304721X 1951-05-07

Publications (1)

Publication Number Publication Date
CH304721A true CH304721A (en) 1955-01-31

Family

ID=6119205

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304721D CH304721A (en) 1951-05-07 1952-04-28 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH304721A (en)

Similar Documents

Publication Publication Date Title
CH286500A (en) Process for the preparation of a monoazo dye.
CH238459A (en) Process for the preparation of a copper-compatible polyazo dye.
CH304721A (en) Process for the preparation of an azo dye.
DE870304C (en) Process for the production of azo dyes
CH208541A (en) Process for the preparation of a disazo dye.
CH268843A (en) Process for the production of a new dye.
CH251879A (en) Process for the production of a new azo dye.
CH241152A (en) Process for the preparation of a new monoazo dye.
CH302038A (en) Process for the preparation of a chromable disazo dye.
CH302036A (en) Process for the preparation of a chromable disazo dye.
CH267873A (en) Process for the production of a new azo dye.
CH197176A (en) Process for the preparation of a black disazo dye.
CH181809A (en) Process for the preparation of an azo dye.
CH159047A (en) Process for the preparation of a primary disazo dye.
CH273617A (en) Process for the preparation of a monoazo dye.
CH243007A (en) Process for the preparation of a new yellow wool dye.
CH159051A (en) Process for the preparation of a primary disazo dye.
CH159048A (en) Process for the preparation of a primary disazo dye.
CH302020A (en) Process for the preparation of an azo dye.
CH241157A (en) Process for the preparation of a new monoazo dye.
CH293868A (en) Process for the preparation of a copper-compatible polyazo dye.
CH182595A (en) Process for the preparation of a monoazo dye.
CH159049A (en) Process for the preparation of a primary disazo dye.
CH222995A (en) Process for the preparation of an azo dye.
CH197177A (en) Process for the preparation of a black disazo dye.