CH272486A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272486A
CH272486A CH272486DA CH272486A CH 272486 A CH272486 A CH 272486A CH 272486D A CH272486D A CH 272486DA CH 272486 A CH272486 A CH 272486A
Authority
CH
Switzerland
Prior art keywords
azo dye
dye
red
preparation
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 CH272486A publication Critical patent/CH272486A/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)
  • Optical Filters (AREA)

Description

  

  <B>Verfahren zur</B>     Herstellung   <B>eines</B>     Azofarbatoffes.            hs    wurde     gefunden,    dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       diazotierten        4'-Tertiä.ramyl-2-aminodiphenyl-          äther    mit     1-Oxynaphthalin-3,8-disulfonsäure     vereinigt.  



  Der neue Farbstoff bildet ein rotes Pulver,  (las sieh in Wasser mit roter Farbe löst und        'olle    aus essigsaurem Bade in roten Tönen  färbt.  



  Der beim     vorliegenden    Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-2-amino-          diphenyläther    kann nach an sieh bekannter  Methode durch Kondensation von     4-Tertiä,r-          amvl-1        -oxvbenzol    mit 7 -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  lischem, vorzugsweise     alkalicarbonatalkali-          schem    Medium,     gewünschtenfalls    unter Ver  wendung geeigneter, die Kupplungsreaktion  befördernder Zusätze, wie Alkohol,     Pyridin     usw.  



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

    Die sehwach gelb gefärbte     Diazolösung    wird  bei 00 mit einer Lösung von 35 Teilen des       Dinatriumsalzes    der     1-Oxy        naphthalin-3,8        di-          sulfonsäure    in 330 Teilen einer gesättigten       \atriumearbonatlösung    vermischt. Nach eini  gen Stunden wird der rote Farbstoff durch  Zusatz von     Natriumehlorid        ausgefällt    und ab  filtriert. Der Farbstoff wird in heissem Was  ser gelöst.

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



  <B> Process for </B> production <B> of </B> azo carbate. It has been found that a valuable azo dye is obtained if diazotized 4'-tertiary ramyl-2-aminodiphenyl ether is combined with 1-oxynaphthalene-3,8-disulfonic acid.



  The new dye forms a red powder, (as it dissolves in water with a red color, and it colors oil from an acetic acid bath in red tones.



  The starting material used in the present process 4'-Tertiäramyl-2-aminodiphenyl ether can by known method by condensation of 4-Tertiä, r-amvl-1-oxvbenzene 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 diazotization can as usual, for. B. with hydrochloric acid and sodium nitrite, Runaway leads.



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



  <I> Example: </I> <B> 25.5 </B> parts of 4'-tertiaryamyl-2-amino-1,1'-diphenyl ether are mixed with. 46 parts conc. Triturated with 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 slightly yellow colored diazo solution is mixed at 00 with a solution of 35 parts of the disodium salt of 1-oxynaphthalene-3,8 disulfonic acid in 330 parts of a saturated carbonate solution. After a few hours the red dye is precipitated by the addition of 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 diazotierten 4'-Tertiäramyl-2-aminodiphenyl- ät.her mit 1-Oxynaphthalin-3,8-disulfonsäure vereinigt. Der neue Farbstoff bildet, ein rotes Pul ver, das sich in Wasser mit roter Farbe löst und \Volle aus essigsaurem Bade in roten Tönen färbt. Claim: Process for the production of an azo dye, characterized in that diazotized 4'-tertiaryamyl-2-aminodiphenyl ether is combined with 1-oxynaphthalene-3,8-disulfonic acid. The new dye forms, a red powder that dissolves in water with a red color and colors Volle from acetic acid bath in red tones.
CH272486D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272486A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH272486T 1948-02-26
CH270538T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272486A true CH272486A (en) 1950-12-15

Family

ID=25731197

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272486D CH272486A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272486A (en)

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