CH239338A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH239338A
CH239338A CH239338DA CH239338A CH 239338 A CH239338 A CH 239338A CH 239338D A CH239338D A CH 239338DA CH 239338 A CH239338 A CH 239338A
Authority
CH
Switzerland
Prior art keywords
red
nitrophenyl
methyl
azo dye
pyrazolone
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba 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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH239338A publication Critical patent/CH239338A/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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/38—Trisazo dyes ot the type
    • 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
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • 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
    • C09B35/36—Trisazo dyes of the type
    • C09B35/366—D is diphenyl

Landscapes

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 237187.    Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass ein wertvoller       Azofarbstoff    hergestellt werden kann,     wenn     man     tetrazotiertes        3-Oxy-3'-methoxybenzidin     einerseits mit     :Salicylsäure    und anderseits  mit     1-(3'-Nitrophenyl)-3-methyl-5-pyrazolon     kuppelt.  



  Der neue Farbstoff ist ein grünschwarz  bronzierendes Pulver, das sich in     Wasser        mit          orangebrauner,    in     verdünnten        Atzalkalien    mit  orangeroter und in konzentrierter Schwefel  säure mit rubinroter Farbe löst und Baum  wolle nach dem ein- oder     zweibadigen    Nach  kupferungsverfahren in waschechten, roten  Tönen färbt.  



  Das für das vorliegende Verfahren be  nötigte     3-Oxy-3'-methoxybenzidin    kann nach  den Angaben des Hauptpatentes hergestellt  werden.  



  Die     Tetrazotierung    des     3-Oxy-3'-methoxy-          benzidins    erfolgt in bekannter Weise. Die  Kupplung der     Tetrazoverbindung    mit den  oben genannten     Azokomponenten    wird zweck  mässig in zwei Stufen durchgeführt, derart,    dass man zuerst nur eine     einseitige    Kupplung  m it     Salicylsäure    und hierauf     die    weitere  Kupplung mit     1-(3'-Nitrophenyl)-3-methyl-          5.-pyrazolon        bewirkt.    Beide Kupplungen wer  den zweckmässig in alkalischem,

   zum Beispiel       Alkalicarbonat    oder     Atzalkali    oder beide ent  haltendem,     Medium    durchgeführt.  



       Beispiel:     5,75 g     3-Oxy-3'-methoxybenzidin    werden  in üblicher Weise in Gegenwart von Salz  säure mit     Natriumnitrit        tetrazotiert.    Die klare  Lösung der     Tetrazoverbindung    wird bei 5   mit einer Lösung von 3,5 g     Salicylsäure    und  6 g     Natriumhydroxyd    in 40     cm3    Wasser ver  einigt und das     Gemisch    während 1/2 Stunde  bei     4-6     gerührt. Nach dieser Zeit ist der       Monoazofarbstoff    gebildet.

   Man gibt nun  zum     Kupplungsgemisch    eine Lösung von  5,48 g     1-(3'-Nitrophenyl)-3-methyl-5-pyrazo-          lcn    und 2 g     Natriumhydrogyd    in 50 cm'  Wasser. Man rührt das Gemisch     während     1 Stunde bei 10-12  und 20     Stunden    bei  15-20 . Durch Zusatz von Kochsalz wird      der Farbstoff abgeschieden, dann     abfiltriert     und getrocknet.



  <B> Additional patent </B> to main patent no. 237187. Process for the production of an azo dye. It has been found that a valuable azo dye can be produced if tetrazotized 3-oxy-3'-methoxybenzidine is coupled on the one hand with: salicylic acid and on the other hand with 1- (3'-nitrophenyl) -3-methyl-5-pyrazolone.



  The new dye is a greenish-black bronzing powder that dissolves in water with orange-brown, in dilute caustic alkalis with orange-red and in concentrated sulfuric acid with ruby-red color, and after the one- or two-bath copper plating process, cotton is dyed in washfast red tones.



  The 3-oxy-3'-methoxybenzidine required for the present process can be prepared according to the information in the main patent.



  The tetrazotization of 3-oxy-3'-methoxybenzidine takes place in a known manner. The coupling of the tetrazo compound with the abovementioned azo components is advantageously carried out in two stages, in such a way that first only one coupling with salicylic acid on one side and then the further coupling with 1- (3'-nitrophenyl) -3-methyl-5. -pyrazolone causes. Both couplings are expediently in alkaline,

   for example alkali carbonate or caustic alkali or both containing medium carried out.



       Example: 5.75 g of 3-oxy-3'-methoxybenzidine are tetrazotized with sodium nitrite in the usual manner in the presence of hydrochloric acid. The clear solution of the tetrazo compound is combined at 5 with a solution of 3.5 g of salicylic acid and 6 g of sodium hydroxide in 40 cm3 of water and the mixture is stirred for 1/2 hour at 4-6. After this time the monoazo dye is formed.

   A solution of 5.48 g of 1- (3'-nitrophenyl) -3-methyl-5-pyrazolein and 2 g of sodium hydrogen in 50 cm 'of water is then added to the coupling mixture. The mixture is stirred for 1 hour at 10-12 and 20 hours at 15-20. The dye is deposited by adding sodium chloride, then filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man tetrazotiertes 3-Oxy-3'-methoxybenzidin einer seits mit Salicylsäure und anderseits mit 1- (3'-Nitrophenyl)-3-methyl-5-pyrazolon kup pelt. Claim: Process for the production of an azo dye, characterized in that tetrazotized 3-oxy-3'-methoxybenzidine is coupled on the one hand with salicylic acid and on the other hand with 1- (3'-nitrophenyl) -3-methyl-5-pyrazolone. Der neue Farbstoff ist ein grünschwarz bronzierendes Pulver, das sich in Wasser mit orangebrauner, dn verdünnten Ätzalkalien mit orangeroter und in konzentrierter Schwefel säure mit rubinroter Farbe löst und Baum wolle nach dem ein- oder zweibadigen Nach- kupferungsverfahren in waschechten, roten Tönen färbt. The new dye is a greenish-black bronzing powder that dissolves in water with orange-brown, thinly diluted caustic alkalis with orange-red and in concentrated sulfuric acid with ruby-red color, and cotton after the one or two-bath re-coppering process dyes washable, red tones. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man die Tetrazoverbin- dung zuerst einseitig mit Salicylsäure und hierauf mit 1-(3'-Nitrophenyl)-3-methyl-5- pyrazolon kuppelt. SUBCLAIM: Process according to claim, characterized in that the tetrazo compound is first coupled on one side with salicylic acid and then with 1- (3'-nitrophenyl) -3-methyl-5-pyrazolone.
CH239338D 1942-09-02 1942-09-02 Process for the preparation of an azo dye. CH239338A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH237187T 1942-09-02
CH239338T 1942-09-02

Publications (1)

Publication Number Publication Date
CH239338A true CH239338A (en) 1945-09-30

Family

ID=25728238

Family Applications (5)

Application Number Title Priority Date Filing Date
CH239336D CH239336A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.
CH239338D CH239338A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.
CH239335D CH239335A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.
CH239334D CH239334A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.
CH237187D CH237187A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH239336D CH239336A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.

Family Applications After (3)

Application Number Title Priority Date Filing Date
CH239335D CH239335A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.
CH239334D CH239334A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.
CH237187D CH237187A (en) 1942-09-02 1942-09-02 Process for the preparation of an azo dye.

Country Status (2)

Country Link
CH (5) CH239336A (en)
NL (1) NL60356C (en)

Also Published As

Publication number Publication date
CH239335A (en) 1945-09-30
CH237187A (en) 1945-04-15
NL60356C (en)
CH239334A (en) 1945-09-30
CH239336A (en) 1945-09-30

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