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CH253882A - 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
CH253882A
CH253882A CH253882DA CH253882A CH 253882 A CH253882 A CH 253882A CH 253882D A CH253882D A CH 253882DA CH 253882 A CH253882 A CH 253882A
Authority
CH
Switzerland
Prior art keywords
mole
methyl
diazo
pyrazolone
aminophenyl
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 CH253882A publication Critical patent/CH253882A/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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound

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

Description

  

      Zusatzpatent    zum Hauptpatent Nr. 248805.    Verfahren zur Herstellung eines     Azofarbstoffes    der     Pyrazolonreihe.            Clegenstand    vorliegenden Patentes ist ein       Verfahren    zur Herstellung eines     Azofarb-          stoffes    der     Pyrazolonreihe.    Das Verfahren  ist dadurch gekennzeichnet, dass man 1     Mol     1-     Diazo    - 6 -     nitro    - 2 -     oxy-naphthalin-4-sulf    on-    säure,

   1     Mol        5-Methyl-2-methoxy-l-.diazo-          benzol,    2     Mol        1-(4'-Amino-phenyl)-3-methyl-          5-pyrazolon    und 1     Mol        Phosgen    derart auf  einander einwirken lässt, dass ein     Disazofarb-          stoff    der Formel -  
EMI0001.0023     
         entsteht.     Der neue,     metallisierbare        Disazofarbstoff          stellt    ein dunkles Pulver dar,

   das sich in Was  ser mit dunkelrotbrauner     und    in konzentrier  ter Schwefelsäure mit oranger Farbe löst und       Cellulosefasern    aus dem neutralen     Crlauber-          alzbad    in     rotstichig    braunen Tönen färbt,  welche durch Nachbehandlung mit Kupfer  sulfat in ein Rot von sehr guter     Na.ss-    und       Lichtechtheit    übergehen.  



       Beispiel:          29,5        \feile        1-Diazo-6-nitro-2-oxy-naph.          thalin-4-sulfonsäure    werden mit     4(1,4    Teilen  Harnstoff aus     1-(4'-Amino-phenyl)-3-methyl-          5-pyrazolon    und     Phosgen    bei Eiskühlung in  Gegenwart von     überschüssiger    Soda. zum  Zwischenprodukt vereinigt. Nach einigen  Stunden ist die Bildung des     Zwischenproduk-          tes    beendet.

   Man stumpft die überschüssige       Soda        mit;    Salzsäure auf     bicarbonatische    Reak  tion ab und     kuppelt-    mit der Dia.zoniumver-    Bindung von 13,7 Teilen     5-Methyl-2-methoxy-          l.-amino-benzol        weiter.    Der gebildete     Disazo-          farbstoff    wird mit Salz gefällt, filtriert und  getrocknet.  



  Zu demselben Farbstoff gelangt man,  wenn man 1.     Mol    des     Aminoazofarbstoffes;     erhalten durch Kupplung von     diazotierter        1-          Amino-6-nitro-2-oxy-naphthalin-4-sulfonsäure     mit l     -(4'-Amino-phenyl)    - 3 -     methyl-5-pyrazo-          lon,    und 1.

       Mol    des     Aminoazofarbstoffes,    er  halten durch Kupplung von 5 -     Methyl    - 2     -          methoxy    -1-     diazo    -Benzol mit 1- (4' -     Amino-          phenyl)-3-methyl-5-pyrazolon,    mit     Phosgen    in       sodaalkalischem        Mediurn    bis zum Verschwin  den der freien     Aminogruppen    zum asymme  trischen Harnstoff kondensiert.



      Additional patent to main patent No. 248805. Process for the production of an azo dye of the pyrazolone series. The present patent is a process for the production of an azo dye of the pyrazolone series. The method is characterized in that 1 mole of 1- diazo - 6 - nitro - 2 - oxy-naphthalene-4-sulfonic acid,

   1 mol of 5-methyl-2-methoxy-l-.diazo-benzene, 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 disazo color - substance of the formula -
EMI0001.0023
         arises. The new, metallizable disazo dye is a dark powder,

   which dissolves in water with dark red-brown and concentrated sulfuric acid with an orange color and dyes cellulose fibers from the neutral Crlauberalzbad in reddish brown tones, which after treatment with copper sulfate turn into a red with very good moisture and lightfastness.



       Example: 29.5 \ feile 1-Diazo-6-nitro-2-oxy-naph. Thalin-4-sulfonic acid are combined with 4 (1.4 parts of urea from 1- (4'-aminophenyl) -3-methyl-5-pyrazolone and phosgene with ice-cooling in the presence of excess soda. After a few hours the formation of the intermediate product is finished.

   The excess soda is blunted with it; Hydrochloric acid reacts to bicarbonate reaction and continues to couple with the Dia.zonium connection of 13.7 parts of 5-methyl-2-methoxy-l-aminobenzene. The disazo dye formed is precipitated with salt, filtered and dried.



  The same dye is obtained if you add 1. mole of the aminoazo dye; obtained by coupling diazotized 1-amino-6-nitro-2-oxy-naphthalene-4-sulfonic acid with 1- (4'-aminophenyl) -3-methyl-5-pyrazolone, and 1.

       Mol of the aminoazo dye, he keep by coupling 5 - methyl - 2 - methoxy -1- diazo-benzene with 1- (4 '- aminophenyl) -3-methyl-5-pyrazolone, with phosgene in a soda-alkaline medium until it disappears that of the free amino groups condensed 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 5-Methyl- 2-methoxy-1-diazo-benzol, 2 Mol 1-(4'-Amino- phenyl) - 3 - methyl - 5 - pyrazolon mit 1 Mol Phosgen derart aufeinander einwirken lässt, 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-oxy-naphthalene-4-sulfonic acid, 1 mole of 5-methyl-2-methoxy-1- diazo-benzene, 2 moles of 1- (4'-aminophenyl) - 3 - methyl - 5 - pyrazolone with 1 mole of phosgene can act on one another in such a way that dass ein Disazofarbstoff der Formel EMI0002.0010 entsteht. Der neue metallisierbare Disazofarbstoff stellt ein dunkles Pulver dar, das sich in Was ser mit dunkelrotbrauner und in konzen trierter Schwefelsäure mit orangen Farbe löst und Cellulosefasern aus dem neutralen Glau- bersaIzbad in rotstichig braunen Tönen färbt.; welche durch Nachbehandlung mit Kupfer sulfat in ein Rot von sehr guter Nass- und Lichtechtheit übergehen. that a disazo dye of the formula EMI0002.0010 arises. The new metallizable disazo dye is a dark powder that dissolves in water with dark red-brown and in concentrated sulfuric acid with an orange color and dyes cellulose fibers from the neutral Glauber's salt bath in reddish brown tones .; which after treatment with copper sulfate turn into a red with very good wet and light fastness. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man auf 1 Mol des Harnstoffes des 1- (4'- Amino-phenyl) - 3 -me- thyl-5-pyrazolons nacheinander in beliebiger Reihenfolge 1 Mol 1- Diazo - 6 - nitro - 2 - oxy- naphthalin-4-sulfonsäure und 114To15-M ethyl- 2-methoxy-I-diazo-benzol einwirken lässt. 2. SUBClaims: 1. The method according to claim, characterized in that 1 mole of 1- (4'-aminophenyl) -3-methyl-5-pyrazolone is added to 1 mole of the urea of 1- (4'-aminophenyl) - 6 - nitro - 2 - oxynaphthalene-4-sulfonic acid and 114To15-M ethyl-2-methoxy-1-diazo-benzene. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man das Gemisch der Aminoazofarbstoffe aus 1 Mol 1-Diazo-6- nitro-2-oxy-naphthalin-4-sulfonsäure einer seits, 1 Mol 5-Methyl-2-methoxy-l-diazo-ben- zol anderseits und je einem Mol 1-(4'-Amino- phenyl) Process according to claim, characterized in that the mixture of aminoazo dyes is made from 1 mole of 1-diazo-6-nitro-2-oxy-naphthalene-4-sulfonic acid on the one hand, 1 mole of 5-methyl-2-methoxy-1-diazo -benzene on the other hand and one mole each of 1- (4'-aminophenyl) - 3 -methyl- 5 -pyrazolon mit Phosgen bis zum Verschwinden der primären Amino- gruppen kondensiert. - 3 -methyl- 5 -pyrazolone condensed with phosgene until the primary amino groups disappear.
CH253882D 1945-12-27 1945-12-27 Process for the preparation of an azo dye of the pyrazolone series. CH253882A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH248805T 1945-12-27
CH253882T 1945-12-27

Publications (1)

Publication Number Publication Date
CH253882A true CH253882A (en) 1948-03-31

Family

ID=25729300

Family Applications (1)

Application Number Title Priority Date Filing Date
CH253882D CH253882A (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) CH253882A (en)

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