CH221170A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH221170A
CH221170A CH221170DA CH221170A CH 221170 A CH221170 A CH 221170A CH 221170D A CH221170D A CH 221170DA CH 221170 A CH221170 A CH 221170A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
ethyl
aminobenzene
nitro
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH221170A publication Critical patent/CH221170A/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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung     eines        Azofarbstoffes.       Gegenstand des Hauptpatentes ist ein  Verfahren zur Herstellung eines     Azofarb-          stoffes,    gemäss welchem man     4-Nitro-2-chlor-          1=aminobenzol        diazotiert    und mit .dem sauren       Schwefelsäureester    des     3-(N-Äthyl-phenyl-          amino-)butanols-(1)    kuppelt.  



  Es wurde nun gefunden, dass man eben  falls einen sehr     wertvollen        Azofarbstoff     dann erhält, wenn man     4-Nitro-l-amino-          benzol        diazotiert    und mit dem sauren     Schwe-          felsäureester    des     3-(N-Äthyl-3'-methyl-          phenylamino-)        butanols-(1)    kuppelt.  



       Beispiel:     Man lässt die in     üblicher    Weise aus 13,8  Teilen     4-Nitro-l-aminobenzol    bereitete     Diazo-          verbindung    unter Hinzufügung von Eis in  eine kalte Lösung von 28,7 Teilen des       Schwefelsäureesters    von 3 - (N - Äthyl - 3'     -          methyl-phenylamino-)butanol-(1)

      (erhalten  durch Kondensation von     3-Chlorbutanol    mit       Äthyl-m-toluidin    und Überführung der so  erhaltenen Base durch nachfolgende Einwir-         kung    von     Chlorsulfonsäure    in den     Sulfato-          ester)    einfliessen. Die Kupplung wird durch  allmähliches     Zutrop.fen    von     Natriumhy-          drogydlö3ung    beschleunigt, wobei ein Alkali  überschuss tunlichst zu vermeiden ist; erst  gegen     Sehluss    der Kupplung ist schwach  alkalische Reaktion herzustellen.

   Hiernach  wird     anisgesalzen.    Der erhaltene Farbstoff  ist in Wasser mit roter Farbe löslich und  färbt     Acetatseide    .sehr echt in     Rubintönen.  



  Process for the preparation of an azo dye. The subject of the main patent is a process for the production of an azo dye, according to which 4-nitro-2-chloro-1 = aminobenzene is diazotized and the acidic sulfuric acid ester of 3- (N-ethyl-phenyl-amino) butanol- ( 1) couples.



  It has now been found that a very valuable azo dye is also obtained if 4-nitro-1-aminobenzene is diazotized and treated with the acidic sulfuric acid ester of 3- (N-ethyl-3'-methylphenylamino- ) butanols- (1) coupling.



       Example: The diazo compound, prepared in the usual way from 13.8 parts of 4-nitro-1-aminobenzene, is left with the addition of ice in a cold solution of 28.7 parts of the sulfuric acid ester of 3 - (N - ethyl - 3 '- methyl-phenylamino-) butanol- (1)

      (obtained by condensation of 3-chlorobutanol with ethyl-m-toluidine and conversion of the base thus obtained into the sulfate ester by subsequent action of chlorosulfonic acid). The coupling is accelerated by the gradual dropwise addition of sodium hydroxide solution, an excess of alkali being avoided as far as possible; A weakly alkaline reaction can only be produced when the coupling fails.

   Then anise is salted. The dye obtained is soluble in water with a red color and dyes acetate silk .very real in ruby tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azo- farbstoffes, dadurch gekennzeichnet, dass man 4-Nitro-l-aminobenzol diazotiert und mit dem :sauren Schwefelsäureester des 3-(N- Athyl-3'-methyl-phenylamino-) butanols-(1) kuppelt. Der erhaltene Farbstoff ist in Wasser mit roter Farbe löslich und färbt Acetatseide sehr echt in Rubintönen. PATENT CLAIM: Process for the production of an azo dye, characterized in that 4-nitro-l-aminobenzene is diazotized and with the: acidic sulfuric acid ester of 3- (N-ethyl-3'-methyl-phenylamino) butanol- (1) clutch. The dye obtained is soluble in water with a red color and dyes acetate silk very fast in ruby tones.
CH221170D 1939-05-03 1940-04-09 Process for the preparation of an azo dye. CH221170A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE221170X 1939-05-03
CH216418T 1940-04-09

Publications (1)

Publication Number Publication Date
CH221170A true CH221170A (en) 1942-05-15

Family

ID=25725856

Family Applications (1)

Application Number Title Priority Date Filing Date
CH221170D CH221170A (en) 1939-05-03 1940-04-09 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH221170A (en)

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