CH273306A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

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Publication number
CH273306A
CH273306A CH273306DA CH273306A CH 273306 A CH273306 A CH 273306A CH 273306D A CH273306D A CH 273306DA CH 273306 A CH273306 A CH 273306A
Authority
CH
Switzerland
Prior art keywords
dehydrothio
yellow
acid
tol
ethoxy
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 CH273306A publication Critical patent/CH273306A/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group

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

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden,     dass    man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  die     DiazoverbindLing    der durch Backen des  sauren Sulfates der     Dehydrothio-p-toluidin-          monsulfonsäure    erhältlichen     Dehydrothio-p-          tol-Liidin-disulionsäure    mit     1-Acetoacetylamino-          2-äthoxy-4-chlor-5-methylbenzol    vereinigt.  



  Der neue Farbstoff bildet ein gelbes Pul  ver, das sich in Wasser oder verdünnter     Na-          triumhydroxydlösung    mit gelber und in kon  zentrierter Schwefelsäure mit     oranger    Farbe  löst. Seine direkten Färbungen auf Baum  wolle oder regenerierter Zellulose sind     gTün-          stichig    gelb.  



  Das     1-Acetoacet.ylamino-2-äthoxy-4-chlor-5-          methylbenzol    (Schmelzpunkt<B>133</B> bis     137')    er  hält man z. B. durch Kondensation von     Acet-          essigester    mit     1-Amino-2-äthoxy-4-chlor-5-me-          thylbenzol    (in Chlorbenzol in Gegenwart von       Triäthanolamin).        1-Amino-2-ätlioxy-4-chlor-          5-methylbenzol    kann man aus     1-Formylamino-          2-äthoxy-5-methylbenzol    durch Einwirken von  Chlor und nachfolgende     Verseilung    herstel  len.

   Es schmilzt bei K5 bis<B>65".</B>  



  Die     Diazotierung    der     Dehydrothio-p-tolui-          din-disullonsäure    kann in bekannter Weise,  z. B. mittels Salzsäure und     Natriumnitrit,    vor  genommen werden. Die Kupplung mit der  genannten     Aeeto-acetylverbindung    wird zweck  mässig in schwach saurem bis schwach alka  lischem Medium durchgeführt. Die Aufarbei  tung des erhaltenen     Farbstoffes    kann in übli  cher Weise erfolgen.  



  <I>Beispiel:</I>  Man löst<B>27</B> Teile     1-Acetoaectylamino-2-          äthoxy-4-ehlor-5-methylbenzel    in<B>250</B> Teilen    Wasser und<B>13,5</B> Teilen 30prozentiger     Na-          triumhydroxydlösung    und gibt 20 Teile kri  stallisiertes     Natriumacetat    zu.

   Zu dieser Lö  sung giesst man eine aus 40 Teilen     Dehydro-          tliio-p-toluidin-disulionsäure    (die selber durch  Backen von     Dehydrothio-p-toluidin-monosul-          fonsäure    erhalten wird) mittels<B>25</B> Raumteilen  30prozentiger Salzsäure und der nötigen  Menge Nitrit in bekannter Weise hergestellte       Diazolösung    in dünnem Strahle unter gutem  Rühren bei Zimmertemperatur zu. Man     rühlt     vier Stunden weiter.

   Dann tropft man eine       10prozentige    wässerige Lösung von wasser  freiem     --#\'atriumearbonat    bis zur alkalischen  Reaktion gegen Brillantgelb mir     Farbstofis-Lis-          pension    zu und erwärmt hierauf     auf   <B>50'.</B> Der  Farbstoff wird mit wenig     Natriumehlorid     vollständig     ausgesalzen,        abfiltriert    und ge  trocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if the diazo compound of the dehydrothio-p-tol-liidin-disulionic acid, which can be obtained by baking the acidic sulfate of dehydrothio-p-toluidinemonsulfonic acid, is mixed with 1-acetoacetylamino-2-ethoxy-4 -chlor-5-methylbenzene combined.



  The new dye forms a yellow powder which dissolves in water or dilute sodium hydroxide solution with yellow and in concentrated sulfuric acid with orange color. Its direct dyeing on cotton or regenerated cellulose is beneficial yellow.



  The 1-Acetoacet.ylamino-2-ethoxy-4-chloro-5-methylbenzene (melting point <B> 133 </B> to 137 ') he holds z. B. by condensation of acetoacetic ester with 1-amino-2-ethoxy-4-chloro-5-methylbenzene (in chlorobenzene in the presence of triethanolamine). 1-Amino-2-ätlioxy-4-chloro-5-methylbenzene can be produced from 1-formylamino-2-ethoxy-5-methylbenzene by the action of chlorine and subsequent stranding.

   It melts at K5 to <B> 65 ". </B>



  The diazotization of dehydrothio-p-tolui- din-disullonic acid can be carried out in a known manner, for. B. by means of hydrochloric acid and sodium nitrite, be taken before. The coupling with the aeto-acetyl compound mentioned is expediently carried out in a weakly acidic to weakly alkaline medium. The dye obtained can be worked up in a customary manner.



  <I> Example: </I> <B> 27 </B> parts of 1-acetoaectylamino-2-ethoxy-4-chloro-5-methylbenzel are dissolved in <B> 250 </B> parts of water and <B> 13.5 parts of 30 percent sodium hydroxide solution and 20 parts of crystallized sodium acetate are added.

   One of 40 parts of dehydrothio-p-toluidine-disulionic acid (which is itself obtained by baking dehydrothio-p-toluidine-monosulphonic acid) using 25 parts by volume of 30 percent hydrochloric acid is poured into this solution the necessary amount of nitrite in a known manner prepared diazo solution in a thin stream with thorough stirring at room temperature. You keep churning for four hours.

   Then a 10 percent aqueous solution of anhydrous atrium carbonate is added dropwise until it has an alkaline reaction against brilliant yellow with dye lis- sion and then heated to <B> 50 '. </B> The dye is complete with a little sodium chloride salted out, filtered off and dried.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines Azolarb- stoffes, dadurch gekennzeichnet, dass man die Diazoverbindung der durch Backen des sau ren Sulfates der Dehydrothio-p-tol-Liidin-inono- sulfonsäure erhältlichen Dehydrothio-p-tol-Lü- diii-disulionsä-tire -mit 1-Aeetoaeetyl-amino-2- äthoxy-4-chlor-5-met.liylbeiizol vereinigt. <B> PATENT CLAIM: </B> Process for the production of an azo substance, characterized in that the diazo compound of the dehydrothio-p-tol obtainable by baking the acidic sulfate of dehydrothio-p-tol-liidin-inonosulfonic acid is Lüdiii-disulionsä-tire combined with 1-aeetoaeetyl-amino-2-ethoxy-4-chloro-5-met.liylbeiizol. Der neue Farbstoff bildet ein gelbes Pul ver, das sich in Wasser oder verdünnter Na- triiimliydroxydlösung mit gelber und in kon zentrierter Schwefelsäure mit oranger Farbe löst. Seine direkten Färbungen auf Baum wolle oder regenerierter Zellulose sind grün- stichig gelb. The new dye forms a yellow powder which dissolves in water or dilute sodium hydroxide solution with yellow and in concentrated sulfuric acid with orange color. Its direct dyeing on cotton or regenerated cellulose is greenish yellow.
CH273306D 1949-02-10 1949-02-10 Process for the preparation of an azo dye. CH273306A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH273306T 1949-02-10
CH270541T 1949-02-10

Publications (1)

Publication Number Publication Date
CH273306A true CH273306A (en) 1951-01-31

Family

ID=25731213

Family Applications (1)

Application Number Title Priority Date Filing Date
CH273306D CH273306A (en) 1949-02-10 1949-02-10 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH273306A (en)

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