CH253879A - 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.

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Publication number
CH253879A
CH253879A CH253879DA CH253879A CH 253879 A CH253879 A CH 253879A CH 253879D A CH253879D A CH 253879DA CH 253879 A CH253879 A CH 253879A
Authority
CH
Switzerland
Prior art keywords
mol
pyrazolone
diazo
methyl
nitro
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 CH253879A publication Critical patent/CH253879A/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
    • 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

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 248805.    Verfahren zur Herstellung eines     Azofarbstoffes    der     Pyrazolonreihe.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     Azöfarb-          stoffes    der     Pyrazolonreihe.    Das Verfahren ist  dadurch gekennzeichnet, dass man 1     Mol        1-          Dia.zo-6-nitro-2-oxy-naphthalin-4-sulfonsäure,       1.

       Mol        2-Diazo-naphthalin,    2     Mol        1-(4'-Amino-          phenyl)    - 3 -     methyl    - 5     -pyrazolon    und 1     Mol          Phosgen    derart aufeinander     einwirken    lässt,  dass ein     Disazofarbstoff    der Formel  
EMI0001.0020     
    entsteht.

    Der neue,     metallisierbare        Disazofarbstoff     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     rotstiehig    braunen Tönen färbt;  welche durch Nachbehandlung mit Kupfer  sulfat in ein Rot von sehr guter Nass- und  Lichtechtheit übergehen.  



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

   Den erhaltenen     Monoäzofarb-          stoff    kuppelt man alsdann in     la.ekmusneutra-          lern    Medium mit der     Diazoniumverbindung     aus 14,3 Teilen     2-Amino-naphthalin    zum     Dis-          azofarbstoff    weiter und isoliert den Farbstoff  mit Kochsalz.

      Zu demselben Farbstoff gelangt man,  wenn man 1     Mol    des     Aminoazofarbstoffes,     erhalten 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,    er  balten durch Kupplung von     2-Diazo-naph-          thalin    mit     1-(4'-Amino-phenyl)-3-methyl-5-          pyrazolon,

      mit     Phosgen    in     sodaalkalischem     Medium bis zum Verschwinden der freien       Aminogruppen    zum asymmetrischen Harn  stoff kondensiert.



  <B> Additional patent </B> to main patent no. 248805. Process for the production of an azo dye of the pyrazolone series. The 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 1 mol of 1-Dia.zo-6-nitro-2-oxy-naphthalene-4-sulfonic acid, 1.

       Mol of 2-diazo-naphthalene, 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 dye of the formula
EMI0001.0020
    arises.

    The new, metallizable disazo dye is a dark powder that dissolves in water with a reddish brown color 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.



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

   The monoazo dye obtained is then coupled in an ecmus-neutral medium with the diazonium compound of 14.3 parts of 2-amino-naphthalene to give the disazo dye, and the dye is isolated with sodium chloride.

      The same dye is obtained if 1 mol 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 mole of the aminoazo dye, it was formed by coupling 2-diazo-naphthalene with 1- (4'-aminophenyl) -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 2-Diazo- ri.aphthalin, 2 Mol 1-(4'-Amino-phenyl)-3- methyl-5-pyrazolon und 1 Mol Phosgen der art aufeinander einwirken lässt, PATENT CLAIM: Process for the production of an azo dye of the pyrazolone series, characterized in that 1 mol of 1-diazo-6-nitro-2-oxynaphthalene-4-sulfonic acid, 1 mol of 2-diazo ri.aphthalene, 2 mol 1- (4'-Amino-phenyl) -3-methyl-5-pyrazolone and 1 mole of phosgene can act on one another dass ein Dis- azofarbstoff der Formel EMI0002.0001 entsteht. Der neue, metallisierbare Disazofarbstoff stellt ein dunkles Pulver dar, das sich in Was ser mit rotbrauner und in konzentrierter Schwefelsäure mit oranger Farbe löst und Cellulosefasern aus dem neutralen Glauber- salzbad in rotstichig braunen Tönen färbt. welche durch Nachbehandlung mit Kupfer sulfat in ein Rot von sehr guter Nass- und Lichtechtheit übergehen. UNTERANSPRÜCHE: 1. that a dis azo dye of the formula EMI0002.0001 arises. The new, metallizable disazo dye is a dark powder that dissolves in water with reddish-brown color and in concentrated sulfuric acid with 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. SUBCLAIMS: 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 - ogy- naphthalin-4-sulfonsäure und 1 Mol 2-Diazo- naphthalin einwirken lässt. 2. Process according to patent claim, characterized in that 1 mol of 1- (4'-aminophenyl) -3-methyl-5-pyrazolone is added to 1 mol of the urea of 1- (4'-aminophenyl) -3-methyl-5-pyrazolone one after the other in any order 1 mol of 1- diazo - 6 -nitro - 2 - ogynaphthalene-4-sulfonic acid and 1 mol of 2-diazo naphthalene can act. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man das Gemisch der Aminoazofarbstoffe aus 1 Mol 1-Diazo- 6-nitro-2-ogy-naphthalin-4-sulfonsäure einer seits, 1 Mol 2-Diazonaphthalin anderseits und je einem Mol 1-(4'-Amixio-phenyl)-3-methyl- 5-pyrazolon mit Phosgen bis zum Verschwin den der primären Aminogruppen kondensier. Process according to claim, characterized in that the mixture of aminoazo dyes is made from 1 mole of 1-diazo-6-nitro-2-ogy-naphthalene-4-sulfonic acid on the one hand, 1 mol of 2-diazonaphthalene on the other hand and one mole of 1- ( 4'-Amixio-phenyl) -3-methyl-5-pyrazolone condenses with phosgene until the primary amino groups disappear.
CH253879D 1945-12-27 1945-12-27 Process for the preparation of an azo dye of the pyrazolone series. CH253879A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH248805T 1945-12-27
CH253879T 1945-12-27

Publications (1)

Publication Number Publication Date
CH253879A true CH253879A (en) 1948-03-31

Family

ID=25729297

Family Applications (1)

Application Number Title Priority Date Filing Date
CH253879D CH253879A (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) CH253879A (en)

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