CH271834A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH271834A
CH271834A CH271834DA CH271834A CH 271834 A CH271834 A CH 271834A CH 271834D A CH271834D A CH 271834DA CH 271834 A CH271834 A CH 271834A
Authority
CH
Switzerland
Prior art keywords
blue
azo dye
preparation
red
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 CH271834A publication Critical patent/CH271834A/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.       Es wurde gefunden, dass man zu einem       wertvollen        Azofarbstoff    gelangt, wenn man       diazotiertes        2-Amino-l-n-butyloxy-4-tertiär-          arnylbenzol    mit     1-Beiizoylamiiio-8-oxynaphtha-          lin-3,6-disulfonsäure    vereinigt.  



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



  Das beim vorliegenden Verfahren als     Aus-          gangsstoff    dienende     o-Amiiio-l-n-biityioxy-4-          tertiäramylbenzol    lässt sich beispielsweise her  stellen durch     Nitrierung    von     1-Oxy-4-tertiär-          amylbenzol,        Butylierung    der     Hy        droxylgruppe     und Reduktion des Nitroäthers.  



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



  Die Kupplung erfolgt mit Vorteil in     alka-          lisehem,    vorzugsweise     a.lkaliearbonatalkali-          schem        Medium.     



  <I>Beispiel:</I>  23,5 Teile     ?-Amino-l-n-butvloxv-4-tertiär-          amylbetizol    werden     finit.    140 Teilen     @.'3thylalko-          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    zu  tropfen.

   Diese     Diazolösung    wird bei 00 mit der  Lösung von 51 Teilen des     Dinatriumsalzes    der       1-Benzoylamino-8-oxy        naphthalin-3,6,disulfon-          säure    in 330 Teilen einer gesättigten     Natrium-          carbonatlösung    vermischt. Nach einigen Stun  den wird der blaurote Farbstoff     naeh    Zugabe  von     Natriumchlorid        abfiltriert    und hierauf       wieder    in heissem Wasser gelöst.

   Die Lösung  wird von     geringen    Verunreinigungen     abfil-          tr    fiert und mit so viel N     atr        iumchlorid    versetzt,  dass die Hauptmenge des Farbstoffes gefällt  wird. Dieser wird     abfiltriert,    mit verdünnter  N     atriumchloridlösung    gewaschen und getrock  net.



  Process for the production of an azo carbate. It has been found that a valuable azo dye is obtained if diazotized 2-amino-1-n-butyloxy-4-tertiary-arnylbenzene is combined with 1-beiizoylamino-8-oxynaphthalin-3,6-disulfonic acid.



  The new dye forms a blue-red powder, which dissolves in water with a blue-red color and colors Volle from acetic acid bath in blue-red shades.



  The starting material used in the present process o-Amiiio-1-n-biityioxy-4-tertiary amylbenzene 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 by 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? -Amino-l-n-butvloxv-4-tertiary-amylbetizole become finite. 140 parts of ethyl alcohol mixed. 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 drip in.

   This diazo solution is mixed at 00 with a solution of 51 parts of the disodium salt of 1-benzoylamino-8-oxy naphthalene-3,6-disulphonic 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.

   Minor impurities are filtered off from the solution and sufficient sodium chloride is added to precipitate most of the dye. 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-4-tertiäramyl- benzol mit 1-Benzoylamino-8-oxynaphthalin- 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. PATENT CLAIM: Process for the production of an azo dye, characterized in that diazotized 2-amino-1-n-butyloxy-4-tertiaryamylbenzene is 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 an acetic acid bath in blue-red shades.
CH271834D 1948-02-26 1948-02-26 Process for the preparation of an azo dye. CH271834A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH271834T 1948-02-26
CH268842T 1948-02-26

Publications (1)

Publication Number Publication Date
CH271834A true CH271834A (en) 1950-11-15

Family

ID=25731036

Family Applications (1)

Application Number Title Priority Date Filing Date
CH271834D CH271834A (en) 1948-02-26 1948-02-26 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH271834A (en)

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