CH268842A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH268842A
CH268842A CH268842DA CH268842A CH 268842 A CH268842 A CH 268842A CH 268842D A CH268842D A CH 268842DA CH 268842 A CH268842 A CH 268842A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
parts
blue
red
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 CH268842A publication Critical patent/CH268842A/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
    • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28—Amino naphthols
    • C09B29/30—Amino naphtholsulfonic acid

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

Description

  

  Verfahren zur Herstellung eines     Azofarbatoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotiertes        2-Amino-l-benzyloxy-4-tertiär-          amylbenzol    mit     1-p-Toluolsulfoy        lamino-8-oxy        -          naphthaliri-3,6-disulfonsäure    vereinigt.  



  Der neue     Farbstoff    bildet ein blaurotes  Pulver, das sich in Wasser mit roter Farbe  löst und  'olle aus essigsaurem Bade in  blauroten Tönen färbt.  



  Das beim vorliegenden Verfahren als Aus  gangsstoff dienende     2-Amino-l-benzyloxy-4-          tertiäramylbenzol        lässt    sich beispielsweise     her-          atellen    durch     Nitrierung    von     1-Oxy-4-tertiär-          amylbenzol,        Benzylierung    der     Hy        droxylgruppe     und Reduktion des Nitroäthers.  



  Die     Diazotierung    kann nach bekannten,  für schwer     diazotierbare    Amine üblichen     3Ze-          thoden,    beispielsweise in Gegenwart von  Alkohol oder     Essigsäure    oder mit Hilfe von       Nitrosylschwefelsäure    durchgeführt werden.  



  Die Kupplung erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkalicarbonatalkali-          schem    Medium.  



  <I>Beispiel:</I>  8,1 Teile     2-Amino-l-benzyloxy-4-tertiär-          amvlbenzol    werden in 65 Teilen heissem    Äthylalkohol gelöst und unterhalb<B>300</B> mit  11 Teilen     konz.    Salzsäure versetzt. Diese  alkoholische Lösung des Chlorhydrates wird  unterhalb<B>10'</B> durch Zugabe einer gesättigten  wässerigen Lösung von 2,1 Teilen Natrium  nitrit     diazotiert.    Der Lösung von 16 Teilen  des     Dinatriumsalzes    der     1-p-Toluolsulfoyl-          amino-8-oxynaphthalin-3,6-disulfonsäure    in  150 Teilen Wasser werden noch 10 Teile  wasserfreies N     atriumcarbonat    zugesetzt.

   Hier  auf wird obige     Diazoniumlösung    bei 0  ein  getragen. Die Kupplung ist nach 2 Stunden  beendigt. Der     Farbstoff    wird hierauf     abfiltriert     und getrocknet.



  Process for the production of an azo carbate. It has been found that a valuable azo dye is obtained if diazotized 2-amino-1-benzyloxy-4-tertiary-amylbenzene is combined with 1-p-toluenesulfylamino-8-oxy-naphthalen-3,6-disulfonic acid.



  The new dye forms a blue-red powder, which dissolves in water with a red color and colors ole from acetic acid bath in blue-red tones.



  The 2-amino-1-benzyloxy-4-tertiary amylbenzene used as starting material in the present process can be produced, for example, by nitration of 1-oxy-4-tertiary amylbenzene, benzylation of the hydroxyl group and reduction of the nitro ether.



  The diazotization can be carried out according to known 3-methods customary for amines which are difficult to diazotize, for example in the presence of alcohol or acetic acid or with the aid of nitrosylsulfuric acid.



  The coupling is advantageously carried out in an alkaline, preferably alkaline carbonate-alkaline medium.



  <I> Example: </I> 8.1 parts of 2-amino-1-benzyloxy-4-tertiary amvlbenzene are dissolved in 65 parts of hot ethyl alcohol and concentrated below <B> 300 </B> with 11 parts. Hydrochloric acid added. This alcoholic solution of the chlorohydrate is diazotized below <B> 10 '</B> by adding a saturated aqueous solution of 2.1 parts of sodium nitrite. 10 parts of anhydrous sodium carbonate are added to the solution of 16 parts of the disodium salt of 1-p-toluenesulfoylamino-8-oxynaphthalene-3,6-disulfonic acid in 150 parts of water.

   The above diazonium solution is entered here at 0. The coupling is completed after 2 hours. The dye is then filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man diazotiertes 2-Amino-l-benzyloxy-4-tertiär- amylbenzol mit 1-p-Toluolsulfoylamino-8-oxy- naphthalin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das sich in Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade in blauroten Tönen färbt. PATENT CLAIM: A process for the production of an azo dye, characterized in that diazotized 2-amino-1-benzyloxy-4-tertiary amylbenzene is combined with 1-p-toluenesulfoylamino-8-oxynaphthalene-3,6-disulfonic acid. The new dye forms a blue-red powder that dissolves in water with a red color and dyes wool from an acetic acid bath in blue-red tones.
CH268842D 1948-02-26 1947-04-30 Process for the preparation of an azo dye. CH268842A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH268842T 1948-02-26

Publications (1)

Publication Number Publication Date
CH268842A true CH268842A (en) 1950-06-15

Family

ID=4477035

Family Applications (1)

Application Number Title Priority Date Filing Date
CH268842D CH268842A (en) 1948-02-26 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH268842A (en)

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