CH302391A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH302391A
CH302391A CH302391DA CH302391A CH 302391 A CH302391 A CH 302391A CH 302391D A CH302391D A CH 302391DA CH 302391 A CH302391 A CH 302391A
Authority
CH
Switzerland
Prior art keywords
aminophenyl
dye
azo dye
aryl
sulfonic acid
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 CH302391A publication Critical patent/CH302391A/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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Description

  

  Verfahren zur Herstellung     eines        Azofarbstoffes.       Es wurde gefunden,     da.ss    man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man  eine     Diazoverbindung    des     Aminoazofarbstof-          fes    der Formel         CH3          Aryl-S020    N=N-     @        \@-NH2          OCH3     I       H03S        S03H       in alkalischem Medium mit der     2-[4'-(5"-Ox3--          nal)

  lithyl    - [ 2"] -     aminophenyl)        J    - 6 -     methylbenz.-          tiiiazol-X,7"-disulfonsä.urekuppelt,    in welcher  die in     X-Stellung    befindliche     Sulfonsäure-          gruppe    dieselbe Stellung einnimmt wie die       Sulfonsä        uregruppe    der durch Sulfonieren von       2-(4'        Ainiilophenyl)-6-methylbenzthiazol    mit  tels     konzentrierter    Schwefelsäure erhältlichen  <B><U>'</U></B>-     (4'-Aminophenyl)-6-metllylbenzthiazolsul-          fonsä,

  ure    und nach erfolgter Kupplung den       Ar;vl-SO@>-Rest    abspaltet.  



  Der neue Farbstoff bildet ein schwarzes       Pulver,    das sieh mit blauer Farbe löst     und          Baumwolle    in echten blauen Tönen färbt.  



  Der als     Ausgangsstoff    dienende     Aminoazo-          farbstoff    wird zweckmässig in der Weise her  gestellt, dass man den     4-Chlorbenzolsulfon-          säureester    der     1-Diazo-8-oxyilaplitlialin-3,6-di-          stilfonsäure        finit        1-Amino-2-methoxy-5-metliyl-          lien7o]    in schwach saurem     1Vledium    kuppelt.  



  Die Abspaltung des     4-Chlorbenzolsulfon-          säurerestes    erfolgt zweckmässig durch Erwär  men in stark     alkalischem    Mittel.    64,2 Teile des     Aminoazofarbstoffes,    der er  halten wird, wenn man     diazotierte        1-Amino-8-          (4'    -     chlorbenzolsulfoyloxy)-naphthalin    - 3,6 -     di-          sulfonsälire    mit     1-Amino-2-methoxy-5-methyl-          benzol    in schwach saurem Medium kuppelt,

    werden w     eiterdiazotiert    und mit 55 Teilen  2 - [4'-<B>(5"</B> -     Oxynaphthyl-        [2"]    -     aminophenyl)    ]     -          6-methylbenzthiazol-X,7"-disulfonsäure    in     na-          triumearbonatalka.lischer    Lösung gekuppelt.  Nach vierstündigem Rühren wird das Volu  men auf 1600 Teile eingestellt, auf 75  er  wärmt, 80     Volumteile    einer     301loigen    Na  triumhydroxydlösung zugegeben und 45 Minu  ten bei 78 bis 80  gerührt, zur Abspaltung des       4-Chlorbenzolsulfonsällrerestes.     



  Durch Zugabe von     Natriumchlorid    und  Neutralisieren des     Alkaliübersehusses    mit.  Salzsäure bis fast zum     Neutralpunkt    wird der  neue     Disazofarbstoff    abgeschieden.



  Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if a diazo compound of the aminoazo dye of the formula CH3 aryl-SO20 N = N- @ \ @ - NH2 OCH3 I H03S SO3H in an alkaline medium with the 2- [4 '- (5 "-Ox3-- nal)

  lithyl - [2 "] - aminophenyl) J - 6 - methylbenz.- tiiiazol-X, 7" -disulfonic acid, in which the sulfonic acid group in the X position occupies the same position as the sulfonic acid group obtained by sulfonating 2 - (4'-aminophenyl) -6-methylbenzthiazole with concentrated sulfuric acid available <B><U>'</U> </B> - (4'-aminophenyl) -6-metllylbenzthiazolsulfonsä,

  ure and, after coupling, the Ar; vl-SO @> residue is split off.



  The new dye forms a black powder that dissolves with blue color and dyes cotton in true blue tones.



  The aminoazo dye used as starting material is conveniently prepared in such a way that the 4-chlorobenzenesulfonic acid ester of 1-diazo-8-oxyilaplitlialin-3,6-di-stilfonic acid is finitely 1-amino-2-methoxy-5- metliyllien7o] in weakly acidic 1Vledium.



  The 4-chlorobenzenesulfonic acid residue is expediently split off by heating in a strongly alkaline medium. 64.2 parts of the aminoazo dye, which he will keep if you diazotized 1-amino-8- (4 '- chlorobenzenesulfoyloxy) naphthalene - 3,6 - disulfonic acid with 1-amino-2-methoxy-5-methyl- benzene couples in a weakly acidic medium,

    are further diazotized and with 55 parts of 2- [4'- <B> (5 "- Oxynaphthyl- [2"] - aminophenyl)] - 6-methylbenzthiazol-X.7 "-disulfonic acid in sodium carbonate alkali. After four hours of stirring, the volume is adjusted to 1,600 parts, heated to 75, 80 parts by volume of a 301loigen sodium hydroxide solution are added and the mixture is stirred for 45 minutes at 78 to 80 to split off the 4-chlorobenzenesulphonic residue.



  By adding sodium chloride and neutralizing the excess alkali with. Hydrochloric acid is deposited almost to the neutral point of the new disazo dye.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man eine Diazoverbindung des Aminoazofarbstoffes der Formel CH3 ->-NH2 Aryl-S020 N=N-I OCHS H03S S03H in alkalischem Medium mit der 2-[4'-(5"-Oxy- naphthyl-[2"]-aminophenyl) ]-6-methylbenz- thiazol-X,7"-disulfonsäure kuppelt, Claim: Process for the production of an azo dye, characterized in that a diazo compound of the aminoazo dye of the formula CH3 -> - NH2 Aryl-S020 N = NI OCHS H03S S03H in an alkaline medium with the 2- [4 '- (5 "- Oxynaphthyl- [2 "] - aminophenyl)] -6-methylbenzthiazol-X, 7" -disulfonic acid couples, in welcher die in X-Stellung befindliche Sulfonsäure- gruppe dieselbe Stellung einnimmt wie die Sulfonsäuregruppe der durch Sulfonieren von 2-(4'-Aminophenyl)-6-methylbenzthiazol mit- tels konzentrierter Schwefelsäure erhältlichen - (4'-Aminophenyl) -6-methylbenzthiazolsul- fonsä.ure und nach erfolgter Kupplung den Aryl-SO.-Rest abspaltet. Der nette Farbstoff bildet ein schwarzes Pulver, das sich mit blauer Farbe löst und Baumwolle in echten blauen Tönen färbt. in which the sulfonic acid group in the X position occupies the same position as the sulfonic acid group of the - (4'-aminophenyl) -6-methylbenzthiazolesul obtainable by sulfonating 2- (4'-aminophenyl) -6-methylbenzthiazole with concentrated sulfuric acid - Fonsä.ure and, after coupling, the aryl-SO.-residue is split off. The nice dye forms a black powder that dissolves with blue paint and dyes cotton in true blue tones. CIBA Aktiengesellschaft. CIBA Aktiengesellschaft.
CH302391D 1949-08-25 1950-08-11 Process for the preparation of an azo dye. CH302391A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH285138T 1949-08-25
CH302391T 1950-08-11

Publications (1)

Publication Number Publication Date
CH302391A true CH302391A (en) 1954-10-15

Family

ID=25732479

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302391D CH302391A (en) 1949-08-25 1950-08-11 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (1) CH302391A (en)

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