CH272487A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272487A
CH272487A CH272487DA CH272487A CH 272487 A CH272487 A CH 272487A CH 272487D A CH272487D A CH 272487DA CH 272487 A CH272487 A CH 272487A
Authority
CH
Switzerland
Prior art keywords
blue
azo dye
preparation
red
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 CH272487A publication Critical patent/CH272487A/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

Landscapes

  • 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       diazotierten        4'-Tertiäramyl-2-aminodiphenpl-          äther    mit     l.-Benzoylamino-8-oxynaphthalin-          3,6-disulfonsäure    vereinigt,.  



  Der neue Farbstoff bildet ein blaurotes  Pulver, das sich in Wasser mit, blauroter  Farbe löst und Wolle aus     essigsaurem    Bade  in blauroten Tönen färbt..  



  Der beim vorliegenden Verfahren als Aus  gangsstoff dienende     4'-Tertiäramyl-2-amino-          dipheiiyläther    kann nach an sieh bekannter  Methode durch Kondensation von     4-Tertiä.r-          amyl    -1-     oxy        benzol    mit 1- Chlor -     2-nitrobenzol     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Tertiäramyl-2-nitrodiphenyl-          ä        thers    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     alkaliearbonatalkali-          schem        Medium,        gewünsehtenfalls    unter Ver  wendung geeigneter, die Kupplungsreaktion  befördernder     Zusätze,    wie Alkohol,     Py        ridin     usw.  



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

    Die schwach gelb gefärbte     Diazolösung    wird  bei 00 mit der Lösung von 52 Teilen des     Di-          natriumsalzes    der     1-Benzoylainino-8-oxynaph-          tlialin-3,6-disulfonsäure    in 330 Teilen einer ge  sättigten     Natriumearbonatlösung    vermischt.  Nach einigen Stunden wird der blaurote Farb  stoff     abfiltriert    und hierauf in heissem 'Was  ser gelöst. Die Lösung wird von allfälligen       -geringen    Verunreinigungen     abfiltriert    und  mit so viel     Natriumclilorid    versetzt, dass die  Hauptmenge des Farbstoffes gefällt wird.

    Dieser wird     abfiltriert,    mit verdünnter     Na-          triumehloridlösung    gewaschen     Lind    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-aminodiphenyl ether is combined with l-benzoylamino-8-oxynaphthalene-3,6-disulfonic acid.



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



  The starting material used in the present process 4'-Tertiäramyl-2-aminodipheiiyläther can by known method by condensation of 4-Tertiä.r-amyl -1-oxy benzene with 1-chloro - 2-nitrobenzene and subsequent reduction 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, Runaway leads. will.



  The coupling takes place with. Advantage 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> 25.5 parts of 4'-tertiaryamyl-2-amino-1,1'-dipienyl 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 then gradually mixed with a concentrated aqueous solution of 7.2 parts of nat below + <B> 50 </B> .rium nitrite added.

    The pale yellow colored diazo solution is mixed at 00 with a solution of 52 parts of the disodium salt of 1-benzoylainino-8-oxynaphthalene-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, washed with dilute sodium chloride solution and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man diazotierten 4'-Tertiäramyl-2-aminodiphenyl- ätlier mit 1-Benzoy1amino-8-oxynaphthalin- 3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das sich in Wasser mit blauroter Farbe löst und Wolle aus essigsaurem Bade in blauroten Tönen färbt. PATENT CLAIM: A process for the production of an azo dye, characterized in that diazotized 4'-tertiaryamyl-2-aminodiphenyl ethers are combined with 1-benzoylamino-8-oxynaphthalene-3,6-disulfonic acid. The new dye forms a blue-red powder that dissolves in water with a blue-red color and dyes wool from acetic acid bath in blue-red shades.
CH272487D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272487A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH270538T 1948-02-26
CH272487T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272487A true CH272487A (en) 1950-12-15

Family

ID=25731198

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272487D CH272487A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272487A (en)

Similar Documents

Publication Publication Date Title
CH286500A (en) Process for the preparation of a monoazo dye.
CH272487A (en) Process for the preparation of an azo dye.
CH272483A (en) Process for the preparation of an azo dye.
CH272484A (en) Process for the preparation of an azo dye.
CH272486A (en) Process for the preparation of an azo dye.
CH272480A (en) Process for the preparation of an azo dye.
CH272492A (en) Process for the preparation of an azo dye.
CH272488A (en) Process for the preparation of an azo dye.
CH272494A (en) Process for the preparation of an azo dye.
CH272482A (en) Process for the preparation of an azo dye.
CH271835A (en) Process for the preparation of an azo dye.
CH273404A (en) Process for the preparation of a monoazo dye.
CH270538A (en) Process for the preparation of an azo dye.
CH263513A (en) Process for the preparation of an azo dye.
CH272485A (en) Process for the preparation of an azo dye.
CH262279A (en) Process for the preparation of an azo dye.
CH263515A (en) Process for the preparation of an azo dye.
CH263514A (en) Process for the preparation of an azo dye.
CH272495A (en) Process for the preparation of an azo dye.
CH272490A (en) Process for the preparation of an azo dye.
CH263538A (en) Process for the preparation of a disazo dye.
CH272493A (en) Process for the preparation of an azo dye.
CH268842A (en) Process for the preparation of an azo dye.
CH268075A (en) Process for the preparation of an azo dye.
CH271834A (en) Process for the preparation of an azo dye.