CH272495A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272495A
CH272495A CH272495DA CH272495A CH 272495 A CH272495 A CH 272495A CH 272495D A CH272495D A CH 272495DA CH 272495 A CH272495 A CH 272495A
Authority
CH
Switzerland
Prior art keywords
azo dye
parts
preparation
blue
solution
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 CH272495A publication Critical patent/CH272495A/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  dianotierten     4'-Secundäramyl-2-aminodiphe-          nyläther    mit     1-(2',5'-Dichlor)-benzoylamino-8-          oxynaphthalin-3,6-disulfonsäure    vereinigt.  



  Der neue Farbstoff bildet ein blaurotes  Pulver, das Wolle aus     essigsaurem    Bade in  blauroten Tönen färbt.  



  Der beim vorliegenden Verfahren als     Aus-          "giigsstoff        dienende        4'-Secundäramyl-?-amino-          diphenyläther    kann nach an sich bekannter       Bethode    durch Kondensation von     4-SecLmdär-          amyl-l-oxybenzol    mit     1-Chlor-2-nitrobenzol     und nachfolgende Reduktion der Nitrogruppe  des erhaltenen     4'-Secundäramyl-2-nitrodiphe-          npläthers    zur     Aminogruppe    hergestellt  werden.  



  Die Dianotierung kann ebenfalls nach be  kannten, für schwer     diazotierbare    Amine  üblichen Methoden, beispielsweise in Gegen  wart von Alkohol oder Essigsäure oder mit  Hilfe von     Nitrosylschwefelsäure    durchgeführt  werden.  



  Die Kupplung erfolgt. mit Vorteil in     alka-          lisehem,    vorzugsweise     alkalicarbonatalkali-          schem    Medium,     gewünschtenfalls    unter     Ver-          wendung    geeigneter, die     Kupplungsreaktion     befördernder Zusätze wie Alkohol,     Pyridin     usw.  



  <I>Beis</I>     triel:     25,5 Teile     4'-Secuiidäramyl-2-anllno-1,1'-          diphenyläther    der Formel  
EMI0001.0034     
    werden in 100 Teilen     Essigsäure    gelöst. und  hierauf mit. 35 Teilen konzentrierter wässriger       Salzsäurelösuno-        versetzt.    Man lässt bei 5 bis  100 in 30 Minuten eine konzentrierte,     wä.ssrige     Lösung von<B>7.2</B> Teilen N     atriuinnitrit        zutrop-          fen    und erhält nach Verdünnen mit.

   50 Teilen  Eis eine klare, schwach gelblich gefärbte       Diazolösung.    55 Teile der Lösung des     Dina-          triumsalzesder        1-(2',5'-Diehlor-)benzoylamino-          8-oxynaphthalin-3,6-disulfonsäure    in 500 Tei  len Wasser werden mit der 350 warmen Lö  sung von 300 Teilen wasserfreiem. Natrium  carbonat in 1000 Teilen Wasser versetzt. Man  kühlt     äusserlieh    auf 00 und lässt obige     Dia.zo-          lösung    bei 0 bis 50 in 30 Minuten zufliessen.

    Nach einigen     Stunden    wird der blaurote Farb  stoff     abfiltriert,    mit verdünnter Natrium  chloridlösung     ;ewasclien    und getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if dianotated 4'-secondary amyl-2-aminodiphenyl ether is combined with 1- (2 ', 5'-dichloro) -benzoylamino-8-oxynaphthalene-3,6-disulfonic acid .



  The new dye forms a blue-red powder that dyes wool from an acetic acid bath in blue-red shades.



  The 4'-secondary amyl -? - aminodiphenyl ether, which is used as the starting material in the present process, can, according to a known method, by condensation of 4-secondary amyl-1-oxybenzene with 1-chloro-2-nitrobenzene and subsequent reduction of the Nitro group of the 4'-secondary amyl-2-nitrodiphenpläthers obtained to the amino group are produced.



  The dianotation can also be carried out by known methods customary for amines which are difficult to diazotize, for example in the presence of alcohol or acetic acid or with the aid of nitrosylsulfuric acid.



  The coupling takes place. with advantage in alkaline, preferably alkaline carbonate alkaline medium, if desired using suitable additives that promote the coupling reaction, such as alcohol, pyridine, etc.



  <I> Beis </I> triel: 25.5 parts of 4'-Secuiidäramyl-2-anllno-1,1'-diphenyl ether of the formula
EMI0001.0034
    are dissolved in 100 parts of acetic acid. and then with. 35 parts of concentrated aqueous hydrochloric acid solution are added. A concentrated, aqueous solution of 7.2 parts of sodium nitrite is added dropwise at 5 to 100 in 30 minutes and is obtained after dilution with.

   50 parts of ice are a clear, pale yellowish colored diazo solution. 55 parts of the solution of the dinatrium salt of 1- (2 ', 5'-Diehlor-) benzoylamino-8-oxynaphthalene-3,6-disulfonic acid in 500 parts of water with the 350 warm solution of 300 parts of anhydrous. Sodium carbonate is added to 1000 parts of water. It is cooled externally to 00 and the above Dia.zo solution is allowed to flow in at 0 to 50 in 30 minutes.

    After a few hours, the blue-red dye is filtered off, washed with dilute sodium chloride solution, washed and dried.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man diazoticrten 4'-Secundä.ramyl-2-aminodiphe- nyläther mit 1-(2',5'-Dichlor)-benzoylamino- 8-oxynapht.halin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das Wolle aus essigsaurem Bade in blauroten Tönen färbt. PATENT CLAIM Process for the production of an azo dye, characterized in that diazotic 4'-secundä.ramyl-2-aminodiphenyl ether with 1- (2 ', 5'-dichloro) -benzoylamino-8-oxynaphth.halin-3, 6-disulfonic acid combined. The new dye forms a blue-red powder that dyes wool from an acetic acid bath in blue-red shades.
CH272495D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH272495A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH270538T 1948-02-26
CH272495T 1948-02-26

Publications (1)

Publication Number Publication Date
CH272495A true CH272495A (en) 1950-12-15

Family

ID=25731206

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272495D CH272495A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272495A (en)

Similar Documents

Publication Publication Date Title
CH272495A (en) Process for the preparation of an azo dye.
CH272481A (en) Process for the preparation of an azo dye.
CH272484A (en) Process for the preparation of an azo dye.
CH272483A (en) Process for the preparation of an azo dye.
CH271835A (en) Process for the preparation of an azo dye.
CH270538A (en) Process for the preparation of an azo dye.
CH262279A (en) Process for the preparation of an azo dye.
CH272487A (en) Process for the preparation of an azo dye.
CH263514A (en) Process for the preparation of an azo dye.
CH268842A (en) Process for the preparation of an azo dye.
CH270539A (en) Process for the preparation of a monoazo dye.
CH302037A (en) Process for the preparation of a chromable disazo dye.
CH272486A (en) Process for the preparation of an azo dye.
CH263513A (en) Process for the preparation of an azo dye.
CH272498A (en) Process for the preparation of a monoazo dye.
CH272480A (en) Process for the preparation of an azo dye.
CH284997A (en) Process for the preparation of a monoazo dye of the pyrazolone series.
CH306271A (en) Process for the preparation of a substantive azo dye.
CH263515A (en) Process for the preparation of an azo dye.
CH306272A (en) Process for the preparation of a substantive azo dye.
CH272488A (en) Process for the preparation of an azo dye.
CH268077A (en) Process for the preparation of an azo dye.
CH302403A (en) Process for the preparation of a trisazo dye.
CH272489A (en) Process for the preparation of an azo dye.
CH284998A (en) Process for the preparation of a monoazo dye of the pyrazolone series.