CH253881A - Process for the preparation of an azo dye of the pyrazolone series. - Google Patents

Process for the preparation of an azo dye of the pyrazolone series.

Info

Publication number
CH253881A
CH253881A CH253881DA CH253881A CH 253881 A CH253881 A CH 253881A CH 253881D A CH253881D A CH 253881DA CH 253881 A CH253881 A CH 253881A
Authority
CH
Switzerland
Prior art keywords
mole
pyrazolone
orange
dye
diazo
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R 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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH253881A publication Critical patent/CH253881A/en

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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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/38—Trisazo dyes ot the type
    • C09B35/48—Trisazo dyes ot the type the component K being heterocyclic

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

Description

  

  Verfahren zur Herstellung eines     Azofarbatoffes    der     Pyrazolonreihe.       Gegenstand vorliegenden Patentes ist. ein  Verfahren zur Herstellung eines     Azofarbstof-          fes    der     Pyrazolonreihe.    Das Verfahren ist da  durch gekennzeichnet,     dass    man 1     Mol        1-          1)iazo-6-nitro-2-oxy-naphthalin-4-stxlfonsäure.       1     Mol        4-(4"-Diazo-benzoylamino)-4'-oxy-3'-          carboxy-1,1'-azobenzol,

      2     Mol        1-(4'-Amino-          phenyl)    - 3 -     methyl    - 5     -pyrazolon    und 1     Mol          Phosgen    derart aufeinander     einwirken        lässt,     dass ein     Trisazofarbstoff    der Formel  
EMI0001.0023     
         entsteht.          Der    neue,     tnetallisierbare        Trisazofarbstoff     stellt ein dunkles Pulver dar,

   das sich in     Was--          se    r mit rotbrauner und in konzentrierter  Schwefelsäure mit oranger Farbe löst und       Cellulosefasern    aus dem neutralen     Glauber-          salzbad    in orangeroten Tönen färbt, welche  durch Nachbehandlung mit Kupfersulfat in  ein Orange von sehr guter Nass- und Licht  echtheit übergehen.  



       Beispiel:          29,5    Teile     1.-Diazo-6-nitro-2-oxy-naph-          thalin-4-sulfonsäure    werden mit 40,4 Teilen       Ilarnstoff    des     1-(4'-Amino-phenyl)-3-methyl-          5-pyrazolons    bei Eiskühlung in Gegenwart  von überschüssiger Soda zum Zwischenpro-    Bukt vereinigt.

   Nach einigen Stunden ist die  Bildung des Zwischenproduktes     beendet.    Man  stumpft die überschüssige Soda mit Salzsäure  auf     bicarbonatische    Reaktion ab und kuppelt  alsdann in     bicarbonatischem    Medium mit der       Diazoverbindung    aus 37,6 Teilen     4-(4"-Amino-          benzoylamino)    -     4'-oxy-3'-carboxy-1,1'-azoben-          zol    zum     Trisazofarbstoff    weiter und isoliert  den Farbstoff mit Kochsalz.  



  Zu demselben Farbstoff gelangt man,  wenn man 1     Mol    des     Aminoazofarbstoffes,    er  halten durch Kupplung von     diazotierter        1-          Amino-6-nitro-2-oxy-naphthalin-4-sulf        onsäure     mit 1-     (4'-Amino-phenyl)-3-methyl-5-pyrazo-          lon    und 1     Mol    des     Aminoazofarbstoffes,    erhal  ten durch Kupplung von     4-(4"-Diazo-benzoyl-          1          amino)-4'-oxy-3'-carboxy-,1'-azobenzol    mit      1- (4'-     Amino-phenyl)

      - 3 -     methyl-5-pyrazolon.     mit     Phosgen    in     sodaalkalischem    Medium bis  zum Verschwindender freien     Aminogruppen     zum asymmetrischen Harnstoff kondensiert.



  Process for the production of an azo carbate of the pyrazolone series. Subject of the present patent is. a process for the production of an azo dye of the pyrazolone series. The process is characterized in that one mole of 1- 1) iazo-6-nitro-2-oxy-naphthalene-4-stxlfonic acid. 1 mole of 4- (4 "-diazo-benzoylamino) -4'-oxy-3'-carboxy-1,1'-azobenzene,

      2 mol of 1- (4'-aminophenyl) -3-methyl-5-pyrazolone and 1 mol of phosgene can act on one another in such a way that a trisazo dye of the formula
EMI0001.0023
         arises. The new, metalizable trisazo dye is a dark powder,

   which dissolves in water with red-brown and in concentrated sulfuric acid with an orange color and dyes cellulose fibers from the neutral Glauber's salt bath in orange-red tones, which after treatment with copper sulfate turn into an orange with very good wet and lightfastness.



       Example: 29.5 parts of 1.-diazo-6-nitro-2-oxy-naphthalene-4-sulfonic acid are mixed with 40.4 parts of ilarnea of 1- (4'-aminophenyl) -3-methyl-5 -pyrazolons combined with ice-cooling in the presence of excess soda to give the intermediate product.

   After a few hours, the formation of the intermediate product has ended. The excess soda is blunted with hydrochloric acid to a bicarbonate reaction and then coupled in a bicarbonate medium with the diazo compound of 37.6 parts of 4- (4 "-amino-benzoylamino) -4'-oxy-3'-carboxy-1,1 ' -azoben- zol to the trisazo dye and isolate the dye with salt.



  The same dye can be obtained if 1 mol of the aminoazo dye is obtained by coupling diazotized 1-amino-6-nitro-2-oxynaphthalene-4-sulfonic acid with 1- (4'-aminophenyl) -3 -methyl-5-pyrazolone and 1 mole of the aminoazo dye obtained by coupling 4- (4 "-diazo-benzoyl-1 amino) -4'-oxy-3'-carboxy-, 1'-azobenzene with 1 - (4'-Amino-phenyl)

      - 3 - methyl-5-pyrazolone. condensed with phosgene in a soda-alkaline medium until the free amino groups disappear to form asymmetric urea.

Claims (1)

PATENTANSPRUCH: . Verfahren zur Herstellung eines Azofarb- stoffes der Pyrazolonreihe, dadurch gekenn- zeichnet, dass man 1 Mol 1-Diazo-6-nitro-2- oxy-naphthalin-4-sulfonsäure, 1 Mol 4-(4"- Diazo - benzoylamino) - 4'- oxy-3'-carboxy-1,1'- azobenzol, 2 Mol 1-(4'-Amino-phenyl) PATENT CLAIM:. Process for the production of an azo dye of the pyrazolone series, characterized in that 1 mole of 1-diazo-6-nitro-2-oxynaphthalene-4-sulfonic acid, 1 mole of 4- (4 "- diazo - benzoylamino) - 4'-oxy-3'-carboxy-1,1'-azobenzene, 2 moles 1- (4'-aminophenyl) -3- methyl-5-pyrazolon und 1 Mol Phosgen der art aufeinander einwirken lässt, dass ein Trisazofarbstoff der Formel EMI0002.0026 entsteht. -3- methyl-5-pyrazolone and 1 mole of phosgene act on one another in such a way that a trisazo dye of the formula EMI0002.0026 arises. Der neue, metallisierbare Trisazofarbstoff stellt ein dunkles Pulver dar, das sich in Wasser mit rotbrauner und in konzentrierter Schwefelsäure mit oranger Farbe löst und Cellulosefasern aus dem neutralen Glauber- salzbad in orangeroten Tönen färbt, welche durch Nachbehandlung mit Kupfersulfat in ein Orange von sehr guter Nass- und Licht echtheit übergehen. EMI0002.0033 EMI0002.0034 The new, metallizable trisazo dye is a dark powder that dissolves in water with red-brown and in concentrated sulfuric acid with an orange color and dyes cellulose fibers from the neutral Glauber's salt bath in orange-red tones, which after treatment with copper sulfate turns into an orange that is very wet - and ignore light authenticity. EMI0002.0033 EMI0002.0034
CH253881D 1945-12-27 1945-12-27 Process for the preparation of an azo dye of the pyrazolone series. CH253881A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH253881T 1945-12-27
CH248805T 1945-12-27

Publications (1)

Publication Number Publication Date
CH253881A true CH253881A (en) 1948-03-31

Family

ID=25729299

Family Applications (1)

Application Number Title Priority Date Filing Date
CH253881D CH253881A (en) 1945-12-27 1945-12-27 Process for the preparation of an azo dye of the pyrazolone series.

Country Status (1)

Country Link
CH (1) CH253881A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE908900C (en) * 1951-06-04 1954-04-12 Geigy Ag J R Process for the production of copperable polyazo dyes
US2714589A (en) * 1951-06-04 1955-08-02 Geigy Ag J R Copperable trisazo dyestuffs

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE908900C (en) * 1951-06-04 1954-04-12 Geigy Ag J R Process for the production of copperable polyazo dyes
US2714589A (en) * 1951-06-04 1955-08-02 Geigy Ag J R Copperable trisazo dyestuffs

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