CH268077A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH268077A
CH268077A CH268077DA CH268077A CH 268077 A CH268077 A CH 268077A CH 268077D A CH268077D A CH 268077DA CH 268077 A CH268077 A CH 268077A
Authority
CH
Switzerland
Prior art keywords
azo dye
preparation
red
dye
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 CH268077A publication Critical patent/CH268077A/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
    • C09B29/10—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)
  • 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-but.yloxy-4-tertiär-          amylbenzol    mit     1-OxYnaphthalin-3,6-disulfon-          säure    vereinigt.  



       Der    neue Farbstoff bildet ein rotes Pul  ver, das sich in Wasser mit roter Farbe löst  und Wolle aus saurem Bade in roten Tönen  färbt.  



  Das beim vorliegenden Verfahren als Aus  gangsstoff dienende     2-Amino-l-n-butyloxy-4-          tertiäramylbenzol    lässt sich beispielsweise her  stellen durch     Nitrierung    von     1-Oxy-4-tert,iär-          amylbenzol,        Butylierung    der     Hydroxylgruppe     und Reduktion des Nitroäthers.  



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



  Die Kupplung erfolgt mit. Vorteil in alka  lischem, vorzugsweise     alkalicarbonatalkali-          schem    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     konz.    Salzsäure zugesetzt, und unterhalb       +    50 lässt man eine     konz.    wässerige Lösung  von 7,2 Teilen     Natriumnitrit        zutropfen.    Diese       Diazolösung    wird bei 00 mit der Lösung von  35 Teilen des     Dinatriumsalzes    der     1-Oxcnaph-          thalin-3,

  6-disulfonsäure    in 330 Teilen einer       gesättigten        Natriumearbonatlösung    vermischt.  Nach einigen Stunden wird der rote Farbstoff  nach Zugabe von     Natriumchlorid        abfiltriert     und hierauf in heissem Wasser gelöst. Die Lö  sung wird geklärt und mit, so viel Natrium  chlorid versetzt, dass der Farbstoff zum gröss  ten Teil wieder ausgefällt wird. Hierauf wird  der Farbstoff     abfiltriert    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-1-n-butyloxy-4-tertiary-amylbenzene is combined with 1-oxynaphthalene-3,6-disulfonic acid.



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



  The 2-amino-l-n-butyloxy-4-tertiary amylbenzene used as starting material in the present process can be produced, for example, by nitration of 1-oxy-4-tert, iäramylbenzene, 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 takes place with. Advantage in alkaline, preferably alkaline 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 conc. Hydrochloric acid is added, and below + 50 a conc. add dropwise aqueous solution of 7.2 parts of sodium nitrite. This diazo solution is mixed at 00 with a solution of 35 parts of the disodium salt of 1-oxenaphthalin-3,

  6-disulfonic acid mixed in 330 parts of a saturated sodium carbonate solution. After a few hours, the red dye is filtered off after adding sodium chloride and then dissolved in hot water. The solution is clarified and enough sodium chloride is added so that most of the dye is precipitated again. The dye is then filtered off and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- st.offes, dadurch gekennzeichnet, dass man di- azotiertes 2-Amino-l-n-butyloxy-4-tertiäramyl- benzol mit 1-Oxynaphthalin-3,6-disulfonsäure vereinigt. Der neue Farbstoff bildet ein rotes Pul ver, das sich in Wasser mit roter Farbe löst und Wolle aus saurem Bade in roten Tönen färbt. PATENT CLAIM: A process for the production of an azo dye, characterized in that diazo-2-amino-1-n-butyloxy-4-tertiaryamylbenzene is combined with 1-oxynaphthalene-3,6-disulfonic acid. The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acid bath in red shades.
CH268077D 1947-04-30 1947-04-30 Process for the preparation of an azo dye. CH268077A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH268077T 1947-04-30
CH262279T 1947-04-30

Publications (1)

Publication Number Publication Date
CH268077A true CH268077A (en) 1950-04-30

Family

ID=25730565

Family Applications (1)

Application Number Title Priority Date Filing Date
CH268077D CH268077A (en) 1947-04-30 1947-04-30 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH268077A (en)

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