CH272491A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH272491A
CH272491A CH272491DA CH272491A CH 272491 A CH272491 A CH 272491A CH 272491D A CH272491D A CH 272491DA CH 272491 A CH272491 A CH 272491A
Authority
CH
Switzerland
Prior art keywords
preparation
azo dye
formula
parts
red
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 CH272491A publication Critical patent/CH272491A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  eine     Diazoverbindung    des Amins der Formel  
EMI0001.0004     
    mit 1     -Oxynaplitlialin-3,6-disulfonsäure    ver  einigt.  



  Der neue Farbstoff bildet ein rotes Pul  ver, das sieh in siedendem Wasser mit roter  Farbe löst und Wolle scharlachrot färbt.  



  Die beim vorliegenden Verfahren als Aus  gangsstoff dienende Verbindung der obigen  Formel kann nach an sich bekannter     Methode     durch Kondensation des     4-Oetpl-7-oxvl)enzols     der Formel  
EMI0001.0008     
    mit     1.-Chlor-2-nitrobenzol    und nachfolgende  Reduktion der Nitrogruppe des erhaltenen  Nitroäthers zur     Aminogruppe    hergestellt wer  den.  



  Die     Diazotierung    kann wie üblich, z. B. mit  Salzsäure und     Natriumnitrit,    durchgeführt  werden.  



  Die Kupplung erfolgt mit Vorteil in alka  lischem,     vorzugsweise        alkaliearbonatalkali-          schem    Medium.         .Beispiel:     29,7 Teile     4'-Oct.yl-2-ainino-1,1'-diplienyl-          äther    der Formel  
EMI0001.0019     
    werden mit 100 Teilen konzentrierter Salz  säure verrieben. Nach einigen Stunden wird  das zuerst schmierig anfallende Chlorhydrat  fest und kann durch     Zusatz    einer gesättigten  wässerigen     Lösung    von 7,2 Teilen Natrium  nitrit     diazotiert    werden.

   Die schwach gelb ge  färbte     Diazolösung    wird bei     011    mit einer Lö  sung von 35 Teilen des     Dinatriumsalzes    der       1-Oxynaphthalin-3,6-disulfonsäure    in 800 Tei  len einer gesättigten     Natriumcarbonatlösung     vermischt. Der rote, sofort entstehende Farb  stoff wird nach einiger Zeit     abfiltriert    und  getrocknet.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained by using a diazo compound of the amine of the formula
EMI0001.0004
    united with 1-oxynaplitlialin-3,6-disulfonic acid.



  The new dye forms a red powder which dissolves in boiling water with a red color and dyes wool scarlet.



  The compound of the above formula which is used as starting material in the present process can be prepared by a method known per se by condensation of 4-Oetpl-7-oxvl) enzene of formula
EMI0001.0008
    with 1.-chloro-2-nitrobenzene and subsequent reduction of the nitro group of the nitro ether obtained to the amino group who prepared the.



  The diazotization can as usual, for. B. with hydrochloric acid and sodium nitrite.



  The coupling is advantageously carried out in an alkaline, preferably alkali carbonate-alkaline medium. .Example: 29.7 parts of 4'-Oct.yl-2-ainino-1,1'-diplienyl ether of the formula
EMI0001.0019
    are triturated with 100 parts of concentrated hydrochloric acid. After a few hours, the initially greasy hydrochloride obtained solidifies and can be diazotized by adding a saturated aqueous solution of 7.2 parts of sodium nitrite.

   The slightly yellow colored diazo solution is mixed at 011 with a solution of 35 parts of the disodium salt of 1-oxynaphthalene-3,6-disulfonic acid in 800 parts of a saturated sodium carbonate solution. The red, immediately produced dye is filtered off after a while and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- Stoffes, dadurch gekennzeichnet, dass man eine Diazoverbindung des Amins der Formel EMI0001.0033 mit 1-Oxynaphthalin-3,6-disulfonsä.ure ver einigt. Der neue Farbstoff bildet ein rotes Pulver, das sieh in siedendem Wasser mit roter Farbe löst und Wolle scharlachrot färbt. PATENT CLAIM: Process for the production of an azo color substance, characterized in that a diazo compound of the amine of the formula EMI0001.0033 united with 1-oxynaphthalene-3,6-disulfonic acid. The new dye forms a red powder, which dissolves in boiling water with a red color and dyes wool scarlet.
CH272491D 1948-02-26 1950-03-23 Process for the preparation of an azo dye. CH272491A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH270538T 1948-02-26
CH272491T 1950-03-23

Publications (1)

Publication Number Publication Date
CH272491A true CH272491A (en) 1950-12-15

Family

ID=25731202

Family Applications (1)

Application Number Title Priority Date Filing Date
CH272491D CH272491A (en) 1948-02-26 1950-03-23 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH272491A (en)

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