CH263506A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH263506A
CH263506A CH263506DA CH263506A CH 263506 A CH263506 A CH 263506A CH 263506D A CH263506D A CH 263506DA CH 263506 A CH263506 A CH 263506A
Authority
CH
Switzerland
Prior art keywords
dye
azo dye
acid
preparation
oxynaphthalene
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 CH263506A publication Critical patent/CH263506A/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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass ein wertvoller       Azofarbstoff    hergestellt werden kann, wenn  man     diazotiertes        6-Nitro-4-chlor-2-amino-l-          phenol    mit     2-Oxynaphthalin-6-oxyessigsäure     kuppelt.  



  Der neue Farbstoff stellt ein violett  schwarzes Pulver dar, das sich in Wasser und       verdünnter        Sodalösung    mit     rotst.ichig    blauer,  in konzentrierter     Schwefelsäure    mit violett  roter Farbe löst.. Der Farbstoff färbt Wolle  aus saurem Bade in     blauen    Tönen, die durch       Nachchromieren    in ein sehr echtes     grünstichi-          ges    Grau übergeführt werden.  



  Die     2-Oxvnaplithaliil-6-oxy        essigsäure    kann  wie folgt erhalten werden:  Unter     inerter        Gasatmosphäre    werden 160  Teile     2,6-Dioxynaphtlialin    in 1000 Teilen  Wasser, enthaltend 56 Teile 100     /001        iges        Ka-          liunihydroxyd,    bei 80 bis 850 gelöst.

   Unter  Einhaltung dieser     Temperatur    lässt man un  ter Rühren eine etwa 25     %        ige    neutrale Lösung  von     chloressigsaurem    Kalium, enthaltend 110  Teile     Monochloressigsäure,    innert 2 Stunden  zulaufen. Man erwärmt weitere 4 bis 5 Stun  den auf 90 bis<B>950</B> bis zum Eintritt fast. neu  traler Reaktion. Nach Erkalten der Reak  tionsmasse vervollständigt man die     Abschei-          dung    durch     Aussalzen        und    schwaches An  säuern und filtriert.

   Aus der     Nutsclipaste     lässt sich die     2-0xynaphthalin-6-oxyessigsäure     durch mehrmaliges     Digerieren    mit schwacher       Sodalösung    bei 40 bis 500 ausziehen. Die fil-         trierten        Sodaauszüge    ergeben beim Ansäuern  mit     Salzsäure    eine cremefarbige Fällung der       2-Oxy-naphthalin-6-oxyessigsäure,    die im Ge  gensatz zum Ausgangsmaterial auch in kalter  verdünnter     Sodalösung    klar löslich ist. Man  filtriert ab und trocknet.  



  Die Kupplung erfolgt zweckmässig in al  kalischem, z. B.     Alkalihydroxyd    und gegebe  nenfalls     Alkalicarbonat    enthaltendem     Medium.            Beispiel.:     <B>18,9</B> Teile     6-Nitro-4-chlor-2-amino-l-plienol          v    erden in bekannter Weise     diazotiert    und in  alkalischer Lösung mit 22 Teilen     2-Oxynaph-          tlialin-6-oxyessin.säure    gekuppelt. Nach erfolg  ter Kupplung wird der abgeschiedene Farb  stoff     abfiltriert    und     getroeknet.  



  Process for the preparation of an azo dye. It has been found that a valuable azo dye can be produced by coupling diazotized 6-nitro-4-chloro-2-amino-1-phenol with 2-oxynaphthalene-6-oxyacetic acid.



  The new dye is a purple-black powder that dissolves in water and dilute soda solution with reddish-tinged blue, in concentrated sulfuric acid with purple-red color. The dye dyes wool from acidic baths in blue tones, which by chroming into a very real greenish gray can be transferred.



  The 2-oxynaplithalil-6-oxy acetic acid can be obtained as follows: 160 parts of 2,6-dioxynaphthalene are dissolved in 1000 parts of water, containing 56 parts of 100/001 potassium hydroxide, at 80 to 850 under an inert gas atmosphere.

   While maintaining this temperature, an approximately 25% neutral solution of potassium chloroacetic acid containing 110 parts of monochloroacetic acid is allowed to run in within 2 hours, while stirring. It is heated for another 4 to 5 hours to 90 to <B> 950 </B> until almost entry. neutral reaction. After the reaction mass has cooled down, the separation is completed by salting out and weakly acidifying and then filtered.

   The 2-oxynaphthalene-6-oxyacetic acid can be extracted from the nuts clip paste by digesting it several times with a weak soda solution at 40 to 500. When acidified with hydrochloric acid, the filtered soda extracts produce a cream-colored precipitate of 2-oxynaphthalene-6-oxyacetic acid, which, in contrast to the starting material, is clearly soluble in cold, dilute soda solution. It is filtered off and dried.



  The coupling is expedient in al kalischem, z. B. alkali hydroxide and optionally alkali carbonate-containing medium. Example .: <B> 18.9 </B> parts of 6-nitro-4-chloro-2-amino-1-plienol are diazotized in a known manner and in an alkaline solution with 22 parts of 2-oxynaphthialin-6- oxyicinic acid coupled. After coupling has taken place, the deposited dye is filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di- azotiertes 6-Nitro-4-chlor-2-amino-l.-phenol mit 2-0xynaphthalin-6-oxyessigsäure kuppelt. Der neue Farbstoff stellt ein violett- scllwarzes Pulver dar, das sich in Wasser und verdünnter Sodalösung mit rotstickig blauer, in konzentrierter Schwefelsäure mit violett roter Farbe löst. PATENT CLAIM: Process for the production of an azo dye, characterized in that diazoated 6-nitro-4-chloro-2-amino-1.-phenol is coupled with 2-oxynaphthalene-6-oxyacetic acid. The new dye is a violet-black powder that dissolves in water and a dilute soda solution with a red-sticky blue color, and in concentrated sulfuric acid with a purple-red color. Der Farbstoff färbt Volle aus saurein Bade in blauen Tönen, die durch Nachchromieren in ein sehr echtes grünsticki ges Grau übergeführt werden. The dye dyes Volle from acidic bath in blue tones, which are converted into a very real green-tinged gray by subsequent chrome plating.
CH263506D 1942-12-22 1942-12-22 Process for the preparation of an azo dye. CH263506A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH263506T 1942-12-22
CH257111T 1943-11-04

Publications (1)

Publication Number Publication Date
CH263506A true CH263506A (en) 1949-08-31

Family

ID=25730045

Family Applications (1)

Application Number Title Priority Date Filing Date
CH263506D CH263506A (en) 1942-12-22 1942-12-22 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH263506A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE938144C (en) * 1952-06-26 1956-01-26 Hoechst Ag Process for the preparation of chromable monoazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE938144C (en) * 1952-06-26 1956-01-26 Hoechst Ag Process for the preparation of chromable monoazo dyes

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