CH272493A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272493A
CH272493A CH272493DA CH272493A CH 272493 A CH272493 A CH 272493A CH 272493D A CH272493D A CH 272493DA CH 272493 A CH272493 A CH 272493A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
red
parts
tertiaryamyl
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 CH272493A publication Critical patent/CH272493A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Paper (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       diazotierten        4'-Tertiäramyl-2-aminodipheny        1-          äther    mit     1-Acetylamino-8-oxynaphthalin-4,6-          disulfonsäure    vereinigt.  



  Der neue Farbstoff bildet ein rotes Pul  ver mit     messingfarbenem    Oberflächenglanz,  das sich in siedendem     Wasser    mit roter Farbe  löst. und Wolle aus essigsaurem Bade rein rot  färbt.  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-2-amino-          diphenyläther    kann nach an sich bekannter  Methode durch     Kondensation    von     4-Tertiär-          amyl-l-oxybenzol    mit     1_Chlor-2-nitrobenzol     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tertiärainyl-2-nitrodiphenyl-          äthers    zur     Aminogruppe    hergestellt werden.  



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



  Die     Kupphing    erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkalicarbonatalkali-          schem        liedium.     



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiäramyl-2-amino-1,1'-di-          phenyläther    werden mit 46 Teilen konzen-         trierter    Salzsäure verrieben. Nach einer  Stunde wird die Suspension des Chlorhydrates  mit 120 Teilen einer gesättigten Natrium  chloridlösung     angeschlämmt    und hierauf un  terhalb +50 allmählich     mit    einer konzen  trierten     wässrigen    Lösung von 7,2 Teilen Na  triumnitrit versetzt.

   Die schwach gelb ge  färbte     Diazolösung    wird bei 00 mit der Lö  sung von 41 Teilen des     Dinatriumsalzes    der  1-     Acetylamino-    8 -     oxynaplithalin-4,6-disulfon-          säure    in 500 Teilen einer gesättigten Natrium  carbonatlösung vermischt. Der entstehende  Farbstoff wird     abfiltriert    und hierauf mit  zwei Liter Wasser aufgekocht, heiss filtriert  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-2-aminodipheny 1-ether is combined with 1-acetylamino-8-oxynaphthalene-4,6-disulfonic acid.



  The new dye forms a red powder with a brass-colored surface sheen that dissolves in boiling water with a red color. and wool from acetic acid bath dyes pure red.



  The starting material used in the present process 4'-tertiaryamyl-2-aminodiphenyl ether can be obtained by a method known per se by condensation of 4-tertiary amyl-1-oxybenzene with 1-chloro-2-nitrobenzene and subsequent reduction of the nitro group of the 4 obtained '-Tertiärainyl-2-nitrodiphenyl ethers are produced to the amino group.



  The diazotization can as usual, for. B. carried out with hydrochloric acid and sodium nitrite. will.



  Kupphing is advantageously carried out in alkaline, preferably alkali carbonate alkaline, liedium.



  <I> Example: </I> 25.5 parts of 4'-tertiaryamyl-2-amino-1,1'-diphenyl ether are triturated with 46 parts of concentrated hydrochloric acid. After one hour, the suspension of the chlorohydrate is slurried 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 the solution of 41 parts of the disodium salt of 1-acetylamino-8-oxynaplithalin-4,6-disulfonic acid in 500 parts of a saturated sodium carbonate solution. The resulting dye is filtered off and then boiled with two liters of water, filtered hot and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man diazotierten 4'-Tertiäramyl-2-aminodiphenyl- äther mit 1-Acetylamino-8-oxynaphthalin-4,6- disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pulver mit messingfarbenem Oberflächenglanz, das sich in siedendem Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade rein rot färbt. PATENT CLAIM: A process for the production of an azo dye, characterized in that diazotized 4'-tertiaryamyl-2-aminodiphenyl ether is combined with 1-acetylamino-8-oxynaphthalene-4,6-disulfonic acid. The new dye forms a red powder with a brass-colored surface luster, which dissolves in boiling water with a red color and dyes wool from acetic acid baths pure red.
CH272493D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272493A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272493T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272493A true CH272493A (en) 1950-12-15

Family

ID=25731204

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272493D CH272493A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272493A (en)

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