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CH272489A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272489A
CH272489A CH272489DA CH272489A CH 272489 A CH272489 A CH 272489A CH 272489D A CH272489D A CH 272489DA CH 272489 A CH272489 A CH 272489A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
red
parts
dye
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 CH272489A publication Critical patent/CH272489A/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
    • 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)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  dianotierten     4'-Tertiäranivl-4-aminodiphenvl-          äther    mit.     1-OYynaplitlialin-3,6-disulfonsäure     vereinigt.  



  Der neue Farbstoff     bildet    ein rotes Pulver,  (las     sich    in Wasser mit roter Farbe löst und  Wolle aus essigsaurem Bade rein rot färbt.  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-4-aniino-          diphenyläther    kann nach an sieh bekannter       .Methode    durch Kondensation von     4-Tertiär-          aiiwl-l-oay#henzol    mit     1-Clilor-4-nitrobenzol     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-4-nitrodiphenyl-          äthers    zur     Aininogruppe    hergestellt werden.  



  Die Dianotierung kann wie     üblieli,    z. B. mit  Salzsäure und     Natriumnitrit,    durchgeführt  werden.  



  Die Kupplung erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkaliearbonatalkali-          sehem        Mediiini.     



  <I>Beispiel:</I>  13 Teile     4'-Tert.iäramyl-4-aminodiphenyl-          äther    werden     finit    19 Teilen konzentrierter    Salzsäure verrieben und mit Eis versetzt. Die  weisse     Chlorhydratsuspension    wird bei 00 mit.  einer konzentrierten Lösung von 3,5 Teilen Na  triumnitrit in Wasser vermischt. Man erhält  eine klare     Diazoniumlösung.     



  Der Lösung von 18 Teilen des     Dinatriuni-          salzes    der     1-Oxynaplithalin-3,6-disulfonsäure     in 350 Teilen Wasser werden noch 15 Teile  wasserfreies     Natriumearbona.t    zugesetzt. Obige       Diazoniumlösung    wird bei     0     langsam einge  tragen. Wenn in der braunroten Farbstoff  suspension keine     Diazoniumverbindung    mehr  nachgewiesen werden kann, wird der Farb  stoff abgesaugt, mit verdünnter     Na.trium-          ehloridlösüng        gewaschen    und     getrocknet.  



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if one with dianotated 4'-Tertiäranivl-4-aminodiphenvl- ether. 1-OYynaplitlialin-3,6-disulfonic acid combined.



  The new dye forms a red powder, (can be dissolved in water with a red color, and wool from acetic acid bath dyes pure red.



  The 4'-tertiaryamyl-4-aniino-diphenyl ether used as the starting material in the present process can, according to a known method, by condensation of 4-tertiary aiiwl-l-oay # henzene with 1-chloro-4-nitrobenzene and subsequent reduction the nitro group of the 4'-tertiaryamyl-4-nitrodiphenyl ether obtained to the amino group.



  The Dianotierung can as usual, z. B. with hydrochloric acid and sodium nitrite.



  The coupling is advantageously carried out in alkaline, preferably alkali carbonate alkaline media.



  <I> Example: </I> 13 parts of 4'-tert.iäramyl-4-aminodiphenyl ether are finely triturated with 19 parts of concentrated hydrochloric acid and mixed with ice. The white hydrochloride suspension is at 00 with. a concentrated solution of 3.5 parts of sodium nitrite mixed in water. A clear diazonium solution is obtained.



  A further 15 parts of anhydrous sodium carbonate are added to the solution of 18 parts of the dinatrium salt of 1-oxynaplithalin-3,6-disulfonic acid in 350 parts of water. The above diazonium solution is slowly entered at 0. If no more diazonium compounds can be detected in the brown-red dye suspension, the dye is suctioned off, washed with dilute sodium chloride solution and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man dianotierten 4'-Tertiäi@amyl-4-aminodiphenvl- äther mit 1-OYynaphthalin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pulver, das sieh in Wasser mit roter Farbe löst und .Volle aus essigsaurem Bade rein rot färbt. PATENT CLAIM: A process for the production of an azo dye, characterized in that dianotated 4'-tertiary amyl-4-aminodiphenyl ether is combined with 1-OYynaphthalin-3,6-disulfonic acid. The new dye forms a red powder, which dissolves in water with a red color and turns pure red from acetic acid bath.
CH272489D 1947-04-30 1947-04-30 Process for the preparation of an azo dye. CH272489A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272489T 1947-04-30
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272489A true CH272489A (en) 1950-12-15

Family

ID=25731200

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272489D CH272489A (en) 1947-04-30 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272489A (en)

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