CH272481A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272481A
CH272481A CH272481DA CH272481A CH 272481 A CH272481 A CH 272481A CH 272481D A CH272481D A CH 272481DA CH 272481 A CH272481 A CH 272481A
Authority
CH
Switzerland
Prior art keywords
azo dye
red
preparation
blue
parts
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 CH272481A publication Critical patent/CH272481A/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
    • C09B29/24—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)
  • Optical Filters (AREA)
  • Detergent Compositions (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'-Tertiäramvl-4-ehlor-2-aniinodi-          phenyläther    mit 1- p -     Toluolstllfoylamino    -     #,-          oxynaplitlialin-3,6-disttlfonsiiure        vereinigt.     



  Der neue Farbstoff bildet ein     rotes    Pul  ver, das     siele    in     Wasser    mit     blauroter    Farbe  löst     imcl        Wolle        aus    essigsaurem Bade in blau  roten Tönen färbt.  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-4-ehlor-2-          aminodiplieiiyläther    kann nach an sieh be  kannter Methode durch     Kondensation    von     4-          Tertiärainyl-1.-oxybenzol    mit     1,4-Diclilor-2-ni-          trobenzol    und nachfolgende Reduktion der  Nitrogruppe des erhaltenen     4'-Tertiäramyl-4-          chlor-2-nit.rodiplienyläthers    zur     Aminogruppe     hergestellt werden.  



  Die Dianotierung kann ebenfalls nach be  kannten, für schwer     diazotierbare    Amine übli  chen Methoden, beispielsweise in Gegenwart  von Alkohol oder Essigsäure oder mit Hilfe  von     Nitrosylschwefelsäure,    durchgeführt wer  den.  



  Die Kupplung erfolgt mit. Vorteil in alka  lischem, vorzugsweise     alkalicarbonatalkali-          schem    Medium,     gewünsehtenfalls    unter Ver  wendung geeigneter, die     Kupplungsreaktion     befördernder Zusätze, wie Alkohol,     Pyridin          usw.            Beispiel:

       14,5 Teile     4'-Tei-t.iä.ramyl-4-elilor-2-amino-          diphen        i-läther        werden    in 50 Teilen 100     oloig,er          Essigsäure    gelöst und mit 1.9 Teilen     konz.     Salzsäure     versetzt.    Unterhalb     :5         wird    eine       konzentrierte,    wässerige Lösung von 3,6 Tei  len     Natriunmitrit        zu;

  etropft.    Beim.     Verdiin-          nen    mit Wasser erhält man eine gelbe, klare       Lösung    der     Diazoniumverbindung.     



  Der Lösung von 26 Teilen des     Dinatrium-          salzes    der     1-p-Tol.uolstilfoylamino-8-oxynapli-          t.lialin-3,6-disulfonsäure    in 1200 Teilen Was  ser werden     noeb    120 Teile wasserfreies     Na-          triuniearbonat        zugesetzt.    Obige     Diazonium-          lösung    wird bei 00 langsam eingetragen. Die       Farbstoffbildung    ist nach einigen Stunden be  endigt. Der Farbstoff wird abgesaugt, mit  verdünnter     Natriumchloridlösung    gewaschen       Lind    hierauf getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if dianotated 4'-tertiary-amyl-4-chloro-2-aniinodiphenyl ether is combined with 1- p - toluenesilfoylamino - #, - oxynaplitlialin-3,6-distalfonic acid.



  The new dye forms a red powder which dissolves in water with a blue-red color and dyes wool from an acetic acid bath in blue-red shades.



  The starting material used in the present process 4'-tertiaryamyl-4-chloro-2-aminodiplieiiyläther can be used by a known method by condensation of 4-tertiaryrainyl-1.-oxybenzene with 1,4-dicloro-2-nitrobenzene and subsequent reduction of the nitro group of the 4'-tertiaryamyl-4-chloro-2-nit.rodiplienyl ether obtained to the amino group.



  The dianotation can also be carried out by known 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 takes place with. Advantage in an alkaline, preferably alkaline carbonate alkaline medium, if desired using suitable additives that promote the coupling reaction, such as alcohol, pyridine, etc. Example:

       14.5 parts of 4'-Tei-t.iä.ramyl-4-elilor-2-aminiphen i-ether are dissolved in 50 parts of 100 oily acetic acid and concentrated with 1.9 parts. Hydrochloric acid added. Below: 5, a concentrated, aqueous solution of 3.6 parts of sodium mitrite is added;

  drips. At the. Dilution with water gives a yellow, clear solution of the diazonium compound.



  120 parts of anhydrous sodium carbonate are added to the solution of 26 parts of the disodium salt of 1-p-tol.uolstilfoylamino-8-oxynapli- t.lialin-3,6-disulfonic acid in 1200 parts of water. The above diazonium solution is slowly added at 00. The dye formation is finished after a few hours. The dye is filtered off with suction, washed with dilute sodium chloride solution and then dried.

Claims (1)

PATEN TANSPRUC'IH Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- a.zotierten 4'-Tertiäramyl-4-clilor-2-aminodi- phenyIäther mit 1-p-Toluolsulfoylamino-8- oxynaphthalin-3,6-clisulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pulver, das sich in Wasser mit. blauroter Farbe löst und Wolle aus essigsaurem Bade in blauroten Tönen färbt. PATEN TANSPRUC'IH Process for the production of an azo dye, characterized in that di- a.zotierten 4'-tertiaryamyl-4-chloro-2-aminodiphenyl ether with 1-p-toluenesulfoylamino-8-oxynaphthalene-3,6 -clisulfonic acid combined. The new dye forms a red powder that dissolves in water with. dissolves blue-red paint and dyes wool from acetic acid bath in blue-red shades.
CH272481D 1947-04-30 1947-04-30 Process for the preparation of an azo dye. CH272481A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272481T 1947-04-30
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272481A true CH272481A (en) 1950-12-15

Family

ID=25731192

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272481D CH272481A (en) 1947-04-30 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272481A (en)

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