CH272483A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272483A
CH272483A CH272483DA CH272483A CH 272483 A CH272483 A CH 272483A CH 272483D A CH272483D A CH 272483DA CH 272483 A CH272483 A CH 272483A
Authority
CH
Switzerland
Prior art keywords
azo dye
red
blue
preparation
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 CH272483A publication Critical patent/CH272483A/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

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotierten        4'-Tertiäramyl        Z-amino-diphenyl-          äther    mit     1-Acetylamino-8-oxynaphtlialin-3,6-           < lisulfonsäure    vereinigt.  



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



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiiiramyl-2-amino-          dipheny        lädier    kann nach an sieh bekannter       :Methode    durch Kondensation von     4-Tertiär-          amyl    -1-     oxybenzol.    mit 1-     Chlor-2-nitrobenzol     Und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-2-nitrodiphenyl-          äthers    zur     Aminogruppe    hergestellt werden.  



  Die     Diazotierung    kann wie üblich, z. B.  mit Salzsäure und     Natriumnitrit,    durchge  führt werden.  



  Die Kupplung erfolgt mit Vorteil in     alka-          liscliem,    vorzugsweise     alkaliearbonatalkali-          schein    Medium,     gewünsehtenfalls    unter Ver  wendung geeigneter, die Kupplungsreaktion  befördernder Zusätze, wie Alkohol,     Pyridin     usw.  



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiärainyl-2-amino-1,7'-cli-          phenyläther    werden mit 46 Teilen     konz.    Salz-         säure    verrieben. Nach einer Stunde wird die  Suspension     des    Chlorhydrates mit 120 Teilen  einer gesättigten     Natriumchloridlösung        ange-          sehlämmt    und hierauf unterhalb + 50 allmäh  lich mit einer konzentrierten wässerigen Lö  sung von 7,2 Teilen     Natriumnitrit    versetzt.

    Die schwach gelb gefärbte     Diazolösung    wird  bei 00 mit     cler    Lösung von 41 Teilen des     Di-          natriumsalzes    der     l.-Acetyl-amino-8-oxynaph-          tlialin-3,6-disulfonsäure    in 330 Teilen einer       gesättigten        Natriumcarbonatlösung    vermischt.       Nacli    einigen Stunden wird der blaurote Farb  stoff     abfiltriert    und hierauf in heissem Was  ser gelöst.

   Die Lösung wird von allfälligen  geringen Verunreinigungen     abfiltriert    und  mit so viel     Natriumchlorid    versetzt, dass die  Hauptmenge des Farbstoffes gefällt wird.  Dieser wird     abfiltriert,    mit verdünnter Na  triumchloridlösung     gewasehen    und getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized 4'-tertiaryamyl-Z-aminodiphenyl ether is combined with 1-acetylamino-8-oxynaphthalene-3,6- <isulphonic acid.



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



  The 4'-tertiary amyl-2-aminodipheny used as starting material in the present process can be used according to a known method: method by condensation of 4-tertiary amyl-1-oxybenzene. with 1- chloro-2-nitrobenzene and subsequent reduction of the nitro group of the 4'-tertiaryamyl-2-nitrodiphenyl ether obtained to the amino group.



  The diazotization can as usual, for. B. with hydrochloric acid and sodium nitrite, Runaway leads.



  The coupling is advantageously carried out in alkali, preferably alkali carbonate alkaline medium, if desired using suitable additives that promote the coupling reaction, such as alcohol, pyridine, etc.



  <I> Example: </I> 25.5 parts of 4'-Tertiärainyl-2-amino-1,7'-cliphenyl ether are concentrated with 46 parts. Hydrochloric acid triturated. After one hour, the suspension of the chlorohydrate is lamed with 120 parts of a saturated sodium chloride solution, and a concentrated aqueous solution of 7.2 parts of sodium nitrite is then gradually added below + 50.

    The pale yellow colored diazo solution is mixed at 00 with a solution of 41 parts of the disodium salt of 1.-acetyl-amino-8-oxynaphthalene-3,6-disulfonic acid in 330 parts of a saturated sodium carbonate solution. After a few hours, the blue-red dye is filtered off and then dissolved in hot water.

   Any minor impurities are filtered off from the solution and so much sodium chloride is added that most of the dye is precipitated. This is filtered off, washed with dilute sodium chloride solution and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeiehnet, dass man di anotierten 4' - Tertiäramy1- 2 - amino-diphenyl- äther mit 1-Acetylamino-8-oxynaphthalin-3,6- disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pul ver, das sieh in Wasser mit blauroter Farbe löst und Wolle aus essigsaurem Bade in blau roten Tönen färbt. PATENT CLAIM: Process for the production of an azo dye, characterized in that the anotated 4 '- tertiary amy1-2 - amino-diphenyl ether is combined with 1-acetylamino-8-oxynaphthalene-3,6-disulphonic acid. The new dye forms a red powder that dissolves in water with a blue-red color and dyes wool from an acetic acid bath in blue-red tones.
CH272483D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272483A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272483T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272483A true CH272483A (en) 1950-12-15

Family

ID=25731194

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272483D CH272483A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272483A (en)

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