CH272494A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

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Publication number
CH272494A
CH272494A CH272494DA CH272494A CH 272494 A CH272494 A CH 272494A CH 272494D A CH272494D A CH 272494DA CH 272494 A CH272494 A CH 272494A
Authority
CH
Switzerland
Prior art keywords
blue
azo dye
preparation
red
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 CH272494A publication Critical patent/CH272494A/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

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

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.            1:wurde    gefunden,     dal;    man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotierten        4'-Tex-tiäramyl-2-aminodiphenyl-          iither    mit     l-(2',5'-Dichlor)-benzoylamino-8-          oxynaphthalin-4,6-disulfonsäure    vereinigt.  



  Der neue Farbstoff bildet. ein blaurotes  Pulver, das sich in siedendem Wasser mit  blauroter Farbe löst. und Wolle aus essigsau  rem Bade in echten blauroten Tönen 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-Clilor-2-nitrobenzol.     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-2-nit.rodiphenyl-          ät.hers    zur     Aminogruppe    hergestellt werden.  



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



  Die Kupplung erfolgt mit Vorteil in     alka-          li.sehem,    vorzugsweise     alkalicarbonatalkali-          schein    Medium.  



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiä.ramyl-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     Natriumchlorid-          lösung        angeschlämmt    und hierauf unterhalb       +5()    allmählich     finit    einer konzentrierten     wäss-          rigen    Lösung von 7,2 Teilen     Natriumnitrit     versetzt.

   Die schwach gelb gefärbte     Dia.zolö-          sung    wird bei     01)    mit der Lösung von  50 Teilen des     Dinatriumsalzes    der     1-(2',5'-          Dichlor)-benzoy        lamino-8-oxynaphthalin-4,6-di-          sulfonsäure    in 330 Teilen einer gesättigten       Natriumcarbonatlösung    vermischt. Der entste  hende Farbstoff wird     abfiltriert    und hierauf  aus heissem Wasser umkristallisiert und ge  trocknet.



  Process for the preparation of an azo dye. 1: was found dal; a valuable azo dye is obtained if diazotized 4'-tex-tiäramyl-2-aminodiphenyl iither is combined with 1- (2 ', 5'-dichloro) -benzoylamino-8-oxynaphthalene-4,6-disulfonic acid.



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



  The 4'-tertiaryamyl-2-aminodiphenyl ether used as the starting material in the present process can be prepared 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'-tertiaryamyl-2-nit.rodiphenyl ether obtained to the amino group.



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



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



  <I> Example: </I> 25.5 parts of 4'-tert.ramyl-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 gradually added below +5 ().

   The slightly yellow colored Dia.zolö- solution is at 01) with a solution of 50 parts of the disodium salt of 1- (2 ', 5'-dichloro) -benzoylamino-8-oxynaphthalene-4,6-disulfonic acid in 330 Parts of a saturated sodium carbonate solution mixed. The resulting dye is filtered off and then recrystallized from hot water and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeiehnet, dass man diazotierten 4'-Tertiäramyl-2-aminodiphenyl- äther mit. 1-(2',5'-Diehlor)-benzoylamino-8- oxyna.plitlia.lin-4,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das sieh in siedendem Wasser mit blauroter Farbe löst und Wolle aus essigsau rem Bade in echten blauroten Tönen färbt. PATENT CLAIM: Process for the production of an azo dye, characterized in that diazotized 4'-tertiaryamyl-2-aminodiphenyl ether is used. 1- (2 ', 5'-Diehlor) -benzoylamino-8-oxyna.plitlia.lin-4,6-disulfonic acid combined. The new dye forms a blue-red powder that dissolves in boiling water with a blue-red color and dyes wool from an acetic acid bath in real blue-red shades.
CH272494D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272494A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272494T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272494A true CH272494A (en) 1950-12-15

Family

ID=25731205

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272494D CH272494A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272494A (en)

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