CH271832A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH271832A
CH271832A CH271832DA CH271832A CH 271832 A CH271832 A CH 271832A CH 271832D A CH271832D A CH 271832DA CH 271832 A CH271832 A CH 271832A
Authority
CH
Switzerland
Prior art keywords
blue
azo dye
red
preparation
tertiary
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 CH271832A publication Critical patent/CH271832A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/24Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28Amino naphthols
    • C09B29/30Amino naphtholsulfonic acid

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbatoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff        gelangt,    wenn man       diazotiertes        2-Amino-l-n-butvloxS--4-t.ertiär--          amylbenzol    mit     1-p-Toluolsrilfovjamino-8-oxy-          naphthalin-3,6-disulfonsäure    vereinigt..  



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



  Das beim vorliegenden Verfahren als Aus  gangsstoff dienende     \?-Arnino-l-n-butyloxy-4-          tertiäramylbenzol    lässt sich beispielsweise her  stellen durch     Nitrierung    von     1-Oxy-4-tertiär-          amylbenzol,        Butylierung    der     Hydroxy        l-          gruppe    und Reduktion des Nitroäthers.  



  Die     Diazotierung    kann     naeh    bekannten, für  schwer     diazotierbare    Amine üblichen Metho  den, beispielsweise in Gegenwart von Alkohol  oder Essigsäure, durchgeführt werden.  



  Die Kupplung erfolgt mit Vorteil in alka  lischem, vorzugsweise     alkaliearbonatalkali-          scbem    Medium,.    <I>Beispiel:</I>  23,5 Teile     2-Amino-l-n-butyloxy-4-tertiär-          amylbenzol    werden mit 140 Teilen     Äthylalko-          hol    vermischt.

   Unterhalb +100 werden 35 Teile  konzentrierter Salzsäure zugesetzt und unter-    halb + 50 lässt man eine konzentrierte wässe  rige Lösung von 7,2 Teilen     Natriumnitrit        züi-          tropfen.    Diese     Diazolösung    wird bei     0()    mit der  Lösung von 52 Teilen des     Dinatriumsalzes    der  1- p     @Toluolsulfoy        lamino    -8-     oxynapht.ha.lin    -     3,6,-          disulfonsä.ure    in 330 Teilen einer gesättigten       Natriurnearbonatlösiin,@    vermischt.

   Nach eini  gen<B>'</B> tunden wird der blaurote Farbstoff nach       Zugabe    von     Natriumchlorid        abfiltriert    und  hierauf wieder in heissem Wasser gelöst. Die  Lösung wird von geringen Verunreinigungen       abfiltriert    und mit so viel     Natriumchlorid    ver  setzt, dass die Hauptmenge des Farbstoffes ge  fällt wird. Dieser wird     abfiltriert,    mit ver  dünnter     Natrinmehloridlösung    gewaschen und  getrocknet.



  Process for the production of an azo carbate. It has been found that a valuable azo dye is obtained if diazotized 2-amino-in-butvloxS-4-tertiary-amylbenzene is used with 1-p-toluenesilfovjamino-8-oxynaphthalene-3,6-disulfonic acid united..



  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.



  The amino-1-n-butyloxy-4-tertiary amylbenzene used as the starting material in the present process can be produced, for example, by nitration of 1-oxy-4-tertiary amylbenzene, butylation of the hydroxyl group and reduction of the nitro ether.



  The diazotization can be carried out according to known methods customary for amines which are difficult to diazotize, for example in the presence of alcohol or acetic acid.



  The coupling is advantageously carried out in an alkaline, preferably alkali carbonate alkaline medium. <I> Example: </I> 23.5 parts of 2-amino-1-n-butyloxy-4-tertiary amylbenzene are mixed with 140 parts of ethyl alcohol.

   Below +100, 35 parts of concentrated hydrochloric acid are added and below +50 a concentrated aqueous solution of 7.2 parts of sodium nitrite is added dropwise. This diazo solution is mixed at 0 () with the solution of 52 parts of the disodium salt of 1- p @Toluolsulfoylamino -8- oxynapht.ha.lin - 3,6, - disulfonic acid in 330 parts of a saturated sodium carbonate solution.

   After a few hours, the blue-red dye is filtered off after the addition of sodium chloride and then dissolved again in hot water. Small 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)

P ATEN TAI'TSPRUCH Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet., dass man di- azotiertes 2-Amino-l-n-buti-loxy.4-tertiäramy 1-, Benzol mit 1-p-Toluolsulfoylamino@-8-oxynaph- tlralin-3,6-disulforisäure vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das sich in Wasser mit blauroter Farbe löst und Wolle aus essigsaurem Bade in blau roten Tönen färbt. P ATEN TAI'TSPRUCH Process for the production of an azo dye, characterized in that diazotized 2-amino-ln-buti-loxy.4-tertiary amy1-, benzene with 1-p-toluenesulfoylamino®-8-oxynaph - tlraline-3,6-disulforic acid combined. 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 shades.
CH271832D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH271832A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH271832T 1948-02-26
CH268842T 1948-02-26

Publications (1)

Publication Number Publication Date
CH271832A true CH271832A (en) 1950-11-15

Family

ID=25731034

Family Applications (1)

Application Number Title Priority Date Filing Date
CH271832D CH271832A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH271832A (en)

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