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CH169949A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH169949A
CH169949A CH169949DA CH169949A CH 169949 A CH169949 A CH 169949A CH 169949D A CH169949D A CH 169949DA CH 169949 A CH169949 A CH 169949A
Authority
CH
Switzerland
Prior art keywords
dye
chloro
azo dye
preparation
conc
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH169949A publication Critical patent/CH169949A/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
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
    • 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)

Description

  

  Zusatzpatent zum Hauptpatent     Nr.   <B>163895.</B>    Verfahren zur Darstellung eines     Azofarbstoffes.       Im     Ilauptpatent    ist ein Verfahren zur  Darstellung eines     Azehfarbstoffes    beschrieben,  bei welchem     diazotiertes    2. 4<B>-</B>     Dinitranilin     mit     Bis-(ss-oxäthyl)-m-toluidin    gekuppelt  wird.  



  Es wurde nun gefunden,     dass    man in  analoger Weise einen     Azofarbstoff    von wert  vollen Eigenschaften erhält, wenn man     di-          azotiertes        2-Chlor-4-nitranilin    in stark saurer  Lösung kuppelt mit     2-Bis-(ss-oxäthyl)-amino-          4-ohlor-l-met,hoxybenzol    vom Siedepunkt<B>217</B>  bis<B>225 '/15</B> mm.  



  Der Farbstoff ist ein in Wasser -unlös  liches, dunkles Pulver, das in Alkohol mit       seharlachroter,    in     konz.        Schwefels5,ure    mit       violettroter    Farbe     löslieh    ist und nach dem  üblichen Verfahren     Acetatseide    in schönen,  blaustichig roten Tönen     anfärbt.    Die Fär  bungen zeigen gute Echtheitseigenschaften  und sind rein weiss     ätzbar.    Das neue Pro  dukt ist auch ein gutes Färbemittel für  Lacke.  



  <I>Beispiel:</I>  <B>86</B> Teile     2-Chlor-4-nitranilin    werden in  bekannter Weise mit<B>35</B> Teilen Natrium-         nitrit        und    240 Teilen     konz.    Schwefelsäure  in verdünnter Lösung     diazotiert.    Die     Di-          azoniumlösung    wird nach dem ]Klären mit  <B>123</B> Teilen     2-Bis-(ss-oxäthyl)-amino-4-ohlor-          1-methoxybenzol,    mit der nötigen Menge  Salzsäure gelöst, bei<B>0</B> bis<B>5 '</B> zur Kupplung  gebracht.

   Nach einiger Zeit ist die     Farb-          stoffbildung    beendet, die man durch<B>Ab-</B>  stumpfen der stark sauren Reaktion be  schleunigen kann. Das Endprodukt wird  auf bekannte Weise isoliert,     verpastet    oder,  nach dem Trocknen bei mässig hoher Tem  peratur, zu einem     T'ärbepräparat    verarbeitet.  Es ist ein im Wasser unlösliches, dunkles  Pulver, das sich beispielsweise in Alkohol  mit     scharlacUroter,    in     konz.    Schwefelsäure  mit     violettroter    Farbe löst.



  Additional patent to main patent no. <B> 163895. </B> Process for the preparation of an azo dye. The main patent describes a process for the preparation of an azehic dye, in which diazotized 2,4-dinitraniline is coupled with bis- (s-oxethyl) -m-toluidine.



  It has now been found that an azo dye of valuable properties is obtained in an analogous manner if diazotized 2-chloro-4-nitroaniline is coupled in a strongly acidic solution with 2-bis- (ss-oxethyl) -amino- 4- ohlor-l-met, hoxybenzene with a boiling point of <B> 217 </B> to <B> 225 '/ 15 </B> mm.



  The dye is a water-insoluble, dark powder that is dissolved in alcohol with scarlet red, in conc. Sulfuric acid is soluble in violet-red color and dyes acetate silk in beautiful, bluish-tinged red tones using the usual method. The dyeings show good fastness properties and can be etched in pure white. The new product is also a good colorant for paints.



  <I> Example: </I> <B> 86 </B> parts of 2-chloro-4-nitroaniline are mixed in a known manner with <B> 35 </B> parts of sodium nitrite and 240 parts of conc. Sulfuric acid diazotized in dilute solution. After clarifying with 123 parts of 2-bis- (ss-oxethyl) -amino-4-chloro-1-methoxybenzene, the diazonium solution is dissolved with the necessary amount of hydrochloric acid, at <B> 0 </B> to <B> 5 '</B> brought to the coupling.

   After some time, the formation of the dye has ended, which can be accelerated by <B> dulling </B> the strongly acidic reaction. The end product is isolated in a known manner, pasted or, after drying at a moderately high temperature, processed into a T'ärepreparat. It is a dark powder which is insoluble in water and which, for example, can be found in alcohol with sharp acid, in conc. Dissolves sulfuric acid with a purple-red color.

Claims (1)

PATENTANSPRUCH- Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- azotiertes 2-Chlor-4-nitranilin in stark saurer Lösung kuppelt mit 2-Bis-(ss-oxätliyl)-amino- 4-ehlor-l-methoxybenzol vom Siedepunkt<B>217</B> bis 2#25 '/15 mm. Der Farbstoff ist ein in Wasser unlös- lielies, dunkles Pulver, PATENT CLAIM- Process for the production of an azo dye, characterized in that diazotized 2-chloro-4-nitroaniline is coupled in a strongly acidic solution with 2-bis- (ss-oxätliyl) -amino-4-chloro-1-methoxybenzene from boiling point <B> 217 </B> to 2 # 25 '/ 15 mm. The dye is a water-insoluble, dark powder, das in Alkohol mit scharlachroter, in konz. Schwefelsäure, mit violettroter Farbe löslich ist und nach dem üblichen Verfahren Acetatseide in schönen, blaustichig roteil Tönen anfärbt. Die Fär- biingen zeigen gute Echtheitseigenschaften und sind rein weiss ätzbar. Das neue Pro dukt ist auch ein gutes Färbemittel für Lacke. that in alcohol with scarlet, in conc. Sulfuric acid, is soluble in violet-red color and dyes acetate silk in beautiful, bluish red tones using the usual method. The dye rings show good fastness properties and can be etched in pure white. The new product is also a good colorant for paints.
CH169949D 1933-09-01 1933-09-01 Process for the preparation of an azo dye. CH169949A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH169949T 1933-09-01
CH163895T 1933-09-01

Publications (1)

Publication Number Publication Date
CH169949A true CH169949A (en) 1934-06-15

Family

ID=25717882

Family Applications (1)

Application Number Title Priority Date Filing Date
CH169949D CH169949A (en) 1933-09-01 1933-09-01 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH169949A (en)

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