CH100386A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH100386A
CH100386A CH100386DA CH100386A CH 100386 A CH100386 A CH 100386A CH 100386D A CH100386D A CH 100386DA CH 100386 A CH100386 A CH 100386A
Authority
CH
Switzerland
Prior art keywords
preparation
azo dye
chloro
nitrotoluene
dye
Prior art date
Application number
Other languages
German (de)
Inventor
Griesheim-Elektron Chem Fabrik
Original Assignee
Griesheim Elektron Chem Fab
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 Griesheim Elektron Chem Fab filed Critical Griesheim Elektron Chem Fab
Publication of CH100386A publication Critical patent/CH100386A/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
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

Landscapes

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

Description

  

  Verfahren zur Darstellung eines     Azofarbstoffes.       Es wurde gefunden, dass ein neuer wert  voller     Azofarbstoff    entsteht, wenn man die       Diazoverbindung    von     4-Chlor-2-toluidin    mit  ?.     3-oxynaphtoesäure-5-chlor-o-toluidid        (CH,-:          NH2    : Cl -1.2.5) kuppelt.

   Der Farbstoff  kann für sich allein zwecks Verwendung als  roter Pigmentfarbstoff hergestellt werden, er  kann aber auch auf der vegetabilischen Faser  erzeugt werden und liefert hierbei einen  leuchtend roten klaren Farbton von gegen  über .den bekannten Farbstoffen ähnlicher  Konstitution hervorragender     Bäuchechtheit,          Alkaliechtheit    und     Ätzbarkeit.     



  Von sehr grosser Wichtigkeit ist es, dass  hier ein ausgezeichnetes Verwendungsgebiet  für das     o-Toluidin        bezw.        o-Nitrotoluol    ge  funden ist. Bekanntlich entsteht bei der     Ni-          trierung    von     Toluol    in der Hauptsache     o-Ni-          trotoluol,    neben wenig     p-Nitrotoluol    und  ganz geringen Mengen     m-Nitrotoluol.    Wäh  rend nun für     m-Nitrotoluol    und besonders       p-Nitrotoluol    gute Verwendungsmöglichkei  ten bestanden, musste bisher das     o-Nitrotoluol,

       obwohl es     ini    grössten Prozentsatz zur Ver  fügung stand, als lästiges Abfallprodukt be  trachtet werden.    <I>Beispiel:</I>  Die aus 17,5     gr    salzsaurem     4-Chlor-2-to-          luidin    in üblicher Weise dargestellte     Diazo-          verbindung    lässt     man    unter Rühren in eine  wässerige Suspension von     33        gr        2.3-Oxy-          naphtoesäure-5-chlor-o-toluidid    einfliessen, be  reitet durch Auflösen in Natronlauge und  Wiederausfällen mit verdünnter Essigsäure.

    Der Farbstoff scheidet sich in blauroten  Flocken aus; darauf wird filtriert,     gewaschen     und getrocknet.



  Process for the preparation of an azo dye. It has been found that a new valuable azo dye is created if the diazo compound of 4-chloro-2-toluidine is mixed with?. 3-oxynaphthoic acid-5-chloro-o-toluidide (CH, -: NH2: Cl -1.2.5) couples.

   The dye can be produced on its own for the purpose of using it as a red pigment, but it can also be produced on the vegetable fiber and provides a bright red clear shade with an excellent stomach-fastness, alkali-fastness and etchability compared to the known dyes of a similar constitution.



  It is of very great importance that this is an excellent area of application for o-toluidine or. o-nitrotoluene is found. It is known that the nitration of toluene mainly produces o-nitrotoluene, along with a little p-nitrotoluene and very small amounts of m-nitrotoluene. While m-nitrotoluene and especially p-nitrotoluene were now used well, o-nitrotoluene,

       although it was available in the largest percentage, it should be regarded as an annoying waste product. <I> Example: </I> The diazo compound, prepared in the usual way from 17.5 g of 4-chloro-2-toluidine hydrochloric acid, is left with stirring in an aqueous suspension of 33 g of 2,3-oxynaphthoic acid-5 -fluor chlor-o-toluidide, be prepared by dissolving in sodium hydroxide solution and reprecipitating with dilute acetic acid.

    The dye separates out in blue-red flakes; it is then filtered, washed and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man die Diazoverbindung von 4-Chlor-2-to- luidin mit 2.3-Oxynaplztoesäure-5-chlor-o- toluidid kuppelt. Der neue Farbstoff ist von roter Farbe und die mit ihm auf der Faser hergestellten Färbungen besitzen einen klaren roten Farb ton und sind gegenüber den mit bekannten Farbstoffen ähnlicher Konstitution herge stellten von hervorragender Bäuchechtheit, Alkaliechtheit und Ätzbarkeit. PATENT CLAIM: Process for the preparation of a new azo dye, characterized in that the diazo compound of 4-chloro-2-toluidine is coupled with 2,3-oxynaplztoic acid-5-chloro-o-toluidide. The new dye is red in color and the dyeings produced with it on the fiber have a clear red hue and are compared to those made with known dyes of a similar constitution of excellent stomach fastness, alkali fastness and etchability.
CH100386D 1922-03-14 1922-09-15 Process for the preparation of an azo dye. CH100386A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH99282T 1922-03-14
CH100386T 1922-09-15

Publications (1)

Publication Number Publication Date
CH100386A true CH100386A (en) 1923-07-16

Family

ID=25705510

Family Applications (1)

Application Number Title Priority Date Filing Date
CH100386D CH100386A (en) 1922-03-14 1922-09-15 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH100386A (en)

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