CH268075A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH268075A
CH268075A CH268075DA CH268075A CH 268075 A CH268075 A CH 268075A CH 268075D A CH268075D A CH 268075DA CH 268075 A CH268075 A CH 268075A
Authority
CH
Switzerland
Prior art keywords
azo dye
parts
preparation
red
amino
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 CH268075A publication Critical patent/CH268075A/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
    • C09B29/16—Naphthol-sulfonic acids
    • 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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone

Landscapes

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

Description

  

      Verfahren    zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotiertes        2-Amino-l-methoxy-4-tertiäramyl-          benzol    mit     2-Oxynaphtlialin-6,8-disulfonsäure     vereinigt.  



  Der neue Farbstoff bildet ein rotes Pulver,  das sich in Wasser mit roter Farbe löst und  Wolle aus saurem Bade in     gelbstichig    roten  Tönen färbt.  



  Das beim vorliegenden Verfahren als Aus  gangsstoff dienende     2-Amino-l-methoxy-4-          tertiäramylbenzol    lässt sich beispielsweise her  stellen durch     Nitrierung    von     1-Oxy-4-tertiär-          amylbenzol,        Methylierung    der     Hydroxyl-          gruppe    und Reduktion des Nitroäthers.  



  Die     Diazotierung    kann nach an sich be  kannten Methoden zum Beispiel mit Hilfe von  Salzsäure und     Natriumnitrit    durchgeführt  werden.  



  Die Kupplung erfolgt. mit Vorteil in alka  lischem Medium.  



  <I>Beispiel:</I>  7,8 Teile     2-Amino-l-methoxy-4-tertiärainyl-          benzolwerden    in 70 Teilen Eiswasser und 12  Teilen konzentrierter Salzsäure als Chlor-         hydrat    gelöst und hierauf unterhalb 50 mit  einer konzentrierten Lösung von 2,8 Teilen       Natriumnitrit        diazotiert.     



  Der Lösung von 15 Teilen des     Dinatrium-          salzes    der     2-Oxynaplithalin-6,8-disulfonsäure     in 200 Teilen Wasser werden noch 10 Teile       wasserfreies        Nat.riumearbonat    zugesetzt, wor  auf bei 00 obige     Diazolösung    eingetragen wird.  Die Kupplung findet. nur langsam. statt und  wird nach einigen Stunden     durch    Zusatz von  5 Teilen     Natriumhydroxyd    beschleunigt. Nach  10 Stunden wird die tiefrote Lösung mit Na  triumehlorid versetzt. Der     ausfallende    rote  Farbstoff wird abgesaugt und getrocknet.



      Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized 2-amino-1-methoxy-4-tertiaryamylbenzene is combined with 2-oxynaphthalene-6,8-disulfonic acid.



  The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acid bath in yellowish red tones.



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



  The diazotization can be carried out by methods known per se, for example with the aid of hydrochloric acid and sodium nitrite.



  The coupling takes place. with advantage in alkaline medium.



  <I> Example: </I> 7.8 parts of 2-amino-1-methoxy-4-tertiary-arylbenzene are dissolved in 70 parts of ice water and 12 parts of concentrated hydrochloric acid as the chlorohydrate and then below 50 with a concentrated solution of 2 , 8 parts of sodium nitrite diazotized.



  10 parts of anhydrous sodium carbonate are added to the solution of 15 parts of the disodium salt of 2-oxynaplithalin-6,8-disulfonic acid in 200 parts of water, and the above diazo solution is added at 00. The clutch takes place. only slowly. instead and is accelerated after a few hours by adding 5 parts of sodium hydroxide. After 10 hours, sodium chloride is added to the deep red solution. The red dye which precipitates is filtered off with suction and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- azotiertes 2-Amino-l-metlioxy-4-tertiäramyl- benzol mit 2-Oxynaphthalin-6,8-disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pul ver, das sich in Wasser mit roter Farbe löst und Wolle aus saurem Bade in gelbstichig roten Tönen färbt. Claim: Process for the production of an azo dye, characterized in that diazo-2-amino-1-metlioxy-4-tertiaryamylbenzene is combined with 2-oxynaphthalene-6,8-disulfonic acid. The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acid bath in yellowish red shades.
CH268075D 1947-04-30 1947-04-30 Process for the preparation of an azo dye. CH268075A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH268075T 1947-04-30
CH262279T 1947-04-30

Publications (1)

Publication Number Publication Date
CH268075A true CH268075A (en) 1950-04-30

Family

ID=25730563

Family Applications (1)

Application Number Title Priority Date Filing Date
CH268075D CH268075A (en) 1947-04-30 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH268075A (en)

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