CH271835A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH271835A
CH271835A CH271835DA CH271835A CH 271835 A CH271835 A CH 271835A CH 271835D A CH271835D A CH 271835DA CH 271835 A CH271835 A CH 271835A
Authority
CH
Switzerland
Prior art keywords
azo dye
red
preparation
parts
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 CH271835A publication Critical patent/CH271835A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbatoffes.            I,s    wurde gefunden, dass     inan    zu einem  wertvollen     Azofarbstoff    gelangt, wenn man     di          azotiertes        '-Ainino-l-n-butyloxy-4-isoainylben.-          zol    mit     1-p-Toluolsulfoylamino-8-oxy        napht-ha-          lin-3,6-disulfonsäure    vereinigt.  



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



  Das beim vorliegenden Verfahren als Aus  gangsstoff dienende     2-Amino-l-nr@butyloxy-4-          isoamylbenzol    lässt sieh beispielsweise herstel  len durch     Nitrierung    von     1-0x-          kn        Butylierung    der     Hydroxylgruppe    und Re  duktion des Nitroäthers.  



  Ne     Diazotierung    kann nach bekannten,  für schwer     diazotierbare    Amine üblichen Me  thoden, beispielsweise in Gegenwart von Alko  hol oder     Essigsäure,        dureligeführt    werden.  



  Die     Kupplun-        erfolgt    mit Vorteil in al  kalischem, vorzugsweise     alkalicarbonatalka-          lischem        ,Medium.     



  <I>Beispiel:</I>  23,5 Teile     2-Amino-l-n-buty        loxy--1-isoamyl-          benzol    werden mit 140 Teilen Äthylalkohol  vermischt.. Unterhalb + 100 werden 35 Teile  konzentrierte Salzsäure zugesetzt, und unter-    halb +     50    lässt man eine konzentrierte wässe  rige Lösung von 7,2 Teilen     Natriumnitrit        zu,-          tropfen.    Diese     Diazolösung    wird bei 00 mit  der Lösung von 52 Teilen des     Dinatriumsalzes     der     1-p-Toluolsulfoylamino-8-oxynaphthalin-          3,

  6-disulfonsäure    in 330 Teilen einer gesättig  ten     Natriumcarbonatlösung    vermischt. Nach  einigen Stunden wird der blaurote Farbstoff  nach Zugabe von     Natriumehlorid        abfiltriert     und hierauf wieder in heissem Wasser gelöst.  Die Lösung wird von geringen Verunreinigun  gen     abfiltriert    und mit so viel     Natriumchlorid     versetzt, dass die Hauptmenge des Farbstoffes  gefällt wird. Dieser wird     abfiltriert,    mit ver  dünnter     Natriumchloridlösung    gewaschen und  getrocknet.



  Process for the production of an azo carbate. It has been found that a valuable azo dye is obtained inan if di azo-ainino-ln-butyloxy-4-isoainylben.-zene is combined with 1-p-toluenesulfoylamino-8-oxy naphth-halin-3, 6-disulfonic acid combined.



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



  The 2-amino-1-nr @ butyloxy-4-isoamylbenzene used as starting material in the present process can be produced, for example, by nitration of 1-0x-kn butylation of the hydroxyl group and reduction of the nitro ether.



  Ne 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 alkaline carbonate-alkaline medium.



  <I> Example: </I> 23.5 parts of 2-amino-in-buty loxy - 1-isoamylbenzene 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 allowed to - drop. This diazo solution is mixed at 00 with a solution of 52 parts of the disodium salt of 1-p-toluenesulfoylamino-8-oxynaphthalene-3,

  6-disulfonic acid mixed in 330 parts of a saturated sodium carbonate solution. After a few hours, the blue-red dye is filtered off after addition of sodium chloride and then dissolved again in hot water. Small amounts of 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 di- azotiertes 2-Amino-l-n-butyloxy-l-isoamylben- zol mit 1-p-Toluolsulfoylamino-8-oxynaphtha- lin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein blaurotes Pulver, das sich in Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade in blau roten Tönen färbt. PATENT CLAIM A process for the production of an azo dye, characterized in that diazo-in-butyloxy-1-isoamylbenzene is combined with 1-p-toluenesulfoylamino-8-oxynaphthalin-3,6-disulfonic acid . The new dye forms a bluish-red powder that dissolves in water with a red color and dyes wool from an acetic acid bath in blue-red shades.
CH271835D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH271835A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH268842T 1948-02-26
CH271835T 1948-02-26

Publications (1)

Publication Number Publication Date
CH271835A true CH271835A (en) 1950-11-15

Family

ID=25731037

Family Applications (1)

Application Number Title Priority Date Filing Date
CH271835D CH271835A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH271835A (en)

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