CH272485A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272485A
CH272485A CH272485DA CH272485A CH 272485 A CH272485 A CH 272485A CH 272485D A CH272485D A CH 272485DA CH 272485 A CH272485 A CH 272485A
Authority
CH
Switzerland
Prior art keywords
azo dye
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 CH272485A publication Critical patent/CH272485A/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)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  dianotierten     4'-Tertiärainyl-2-aminodiphenyl-          äther    mit     l.-Oxynaphthalin-3,6-disulfonsäure     vereinigt.  



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



  Der beim vorliegenden Verfahren als     Aus-          gannsstoff    dienende     4'-Tertiäramyl-2-amino-          diphenyläther    kann nach an sich bekannter  Methode durch Kondensation von     4-Tertiär-          aniyl-l-oxybenzol    mit     7.-Chlor-2-nitrobenzol     und nachfolgende     Reduktion    der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-2-nitrodiphenyl-          äthers    zur     Aminogruppe    hergestellt werden.  



  Die Dianotierung kann wie üblich, z. B. mit  Salzsäure und     Natriunmitrit,    durchgeführt  werden.  



  Die Kupplung erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkaliearbonatalkali-          sehem    Medium.  



       Beispiel:     25,5 Teile     4'-Tert.iäramyl-2-amino-7.,1'-di-          plienylät.herwerden    mit     .16    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 all  inählich mit einer konzentrierten wässerigen  Lösung von 7,2 Teilen     Natriumnitrit    versetzt.

    Die schwach gelb gefärbte     Diazolösung    wird  bei 00 mit der Lösung von 35 Teilen des     Di-          natriumsalzes    der     1-Ox-ynaphthalin-3,6-disul-          fonsä.ure    in 330 Teilen einer gesättigten Na  triumcarbonat.lösung vermischt. Nach einigen  Stunden     wird    der rote Farbstoff durch     Zusatz     von     Natriumehlorid    ausgefällt und     abfiltriert.     Der Farbstoff wird in heissem Wasser gelöst.

    Die Lösung wird von allfälligen geringen Ver  unreinigungen     abfiltriert    und mit so viel Na  triumchlorid versetzt, dass der Farbstoff zum  grössten Teil wieder ausgefällt wird. Hierauf  wird der Farbstoff     abfiltriert    und getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if dianotated 4'-tertiaryyl-2-aminodiphenyl ether is combined with l-oxynaphthalene-3,6-disulfonic acid.



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



  The starting material used in the present process 4'-tertiaryamyl-2-aminodiphenyl ether can be prepared according to a method known per se by condensation of 4-tertiary-aniyl-1-oxybenzene with 7-chloro-2-nitrobenzene and subsequent reduction of the Nitro group of the 4'-tertiaryamyl-2-nitrodiphenyl ether obtained to the amino group are prepared.



  The dianotation can be carried out as usual, e.g. B. with hydrochloric acid and sodium mitrite.



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



       Example: 25.5 parts of 4'-tert.iäramyl-2-amino-7., 1'-di-plienyl ether with .16 parts of conc. Triturated with hydrochloric acid. After one hour, the suspension of the chlorohydrate is lamed with 120 parts of a saturated sodium 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 35 parts of the disodium salt of 1-oxynaphthalene-3,6-disulphonic acid in 330 parts of a saturated sodium carbonate solution. After a few hours, the red dye is precipitated by adding sodium chloride and filtered off. The dye is 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 again. The dye is then filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man dianotierten 4'-Tertiäramyl-2-aminodiphenyl- äther mit 1-Oxynaphthalin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pulver, das sich in Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade in seharlaehroten Tönen färbt. Claim: Process for the production of an azo dye, characterized in that dianotated 4'-tertiaryamyl-2-aminodiphenyl ether is combined with 1-oxynaphthalene-3,6-disulfonic acid. The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acetic acid bath in shades of dark red.
CH272485D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272485A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272485T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272485A true CH272485A (en) 1950-12-15

Family

ID=25731196

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272485D CH272485A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272485A (en)

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