CH272484A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

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Publication number
CH272484A
CH272484A CH272484DA CH272484A CH 272484 A CH272484 A CH 272484A CH 272484D A CH272484D A CH 272484DA CH 272484 A CH272484 A CH 272484A
Authority
CH
Switzerland
Prior art keywords
azo dye
blue
red
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 CH272484A publication Critical patent/CH272484A/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.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotierten        4'-Tertiäramyl-2-ainino-diphenyl-          äther    mit     1-p-Toluolsulfoylamino-8-oxynaph-          tlialin-3,6-clisulfonsäure    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-          ,angsstoff    dienende     4'-Tert.iäi-aniyl-2-aniino-          diphenyläther    kann nach an     siele    bekannter  Methode durch Kondensation von     4-Tertiär-          amyl-l-oxybenzol    mit     1-Chlor-2-nitrobenzol     und nachfolgende Reduktion der     Nitrogruppe     des erhaltenen     4'-Tertiäramyl-2-iiitrodiphenyl-          äthers    zur     Aminogruppe    hergestellt werden.  



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



  Die     Kupplung    erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkalicarbonatalkali-          schem    Medium,     gewünschtenfalls    unter Ver  wendung geeigneter, die     Kupplungsreaktion     befördernder     Zusätze,    wie Alkohol,     Pyridin     <B>USW.</B>  



  <I>Beispiel:</I>  25,5 Teile     4'-Tertiäramyl-2-amino-1,7.'-di-          phenyläther    werden mit 46 Teilen     konz.    Salz  säure verrieben. Nach einer Stunde wird die         Suspension    des Chlorhydrates mit 120 Teilen  einer gesättigten     2'#-atriumchloridlösung        a.nge-          schlänmit    und hierauf unterhalb + 50 all  mählich mit einer konzentrierten wässerigen  Lösung von 7,2 Teilen     Natriumnitrit    versetzt.

    Die schwach gelb gefärbte     Diazolösung    wird  bei 00 mit der Lösung von 53 Teilen des     Di-          natriumsalzes    der     1-p-Toluolsulfoylanmino-8-          ox@#napht.halin-3,6-disulfonsäiire    in 330 Teilen  einer gesättigten     Natriumcarbonatlösimg    ver  mischt. Nach einigen Stunden wird der blau  rote Farbstoff     abfiltriert    und hierauf in hei  ssem Wasser gelöst.

   Die Lösung wird von all  fälligen geringen     Verunreinigungen        abfil-          triert    und mit so viel     Natriumehlorid    ver  setzt, dass die Hauptmenge des Farbstoffes  gefällt wird. Dieser wird     abfiltriert,    mit. ver  dünnter     Natrinmehloridlösnng    gewaschen 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-ainino-diphenyl ether is combined with 1-p-toluenesulfoylamino-8-oxynaphthalene-3,6-clisulfonic acid.



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



  The 4'-tert.iäi-aniyl-2-aniino-diphenyl ether, which is used as the starting material in the present process, can be prepared by a method known to many 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.



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



  <I> Example: </I> 25.5 parts of 4'-tertiaryamyl-2-amino-1,7 .'-diphenyl ether are mixed with 46 parts of conc. Triturated with hydrochloric acid. After one hour, the suspension of the chlorohydrate is mixed with 120 parts of a saturated 2% atrium chloride solution and then gradually mixed with a concentrated aqueous solution of 7.2 parts of sodium nitrite below + 50.

    The pale yellow colored diazo solution is mixed at 00 with the solution of 53 parts of the disodium salt of 1-p-toluenesulfoylanmino-8-ox @ # naphth.halin-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 with. Washed diluted sodium chloride solution and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man di anotierten 4' - Tertiäramy l - 2 - ainino-dipheny l- äther mit 1-p-Toluolsulfoylamino-8-oxynapli- tlialin-3,6-disulfonsäure 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. Claim: Process for the production of an azo dye, characterized in that the anotated 4 '- tertiary amy l - 2 - amino-diphenyl ether is combined with 1-p-toluenesulfoylamino-8-oxynapli- tlialine-3,6-disulfonic 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.
CH272484D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272484A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH270538T 1948-02-26
CH272484T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272484A true CH272484A (en) 1950-12-15

Family

ID=25731195

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272484D CH272484A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272484A (en)

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