CH302394A - Process for the preparation of an azo dye. - Google Patents

Process for the preparation of an azo dye.

Info

Publication number
CH302394A
CH302394A CH302394DA CH302394A CH 302394 A CH302394 A CH 302394A CH 302394D A CH302394D A CH 302394DA CH 302394 A CH302394 A CH 302394A
Authority
CH
Switzerland
Prior art keywords
aminophenyl
sulfonic acid
methylbenzthiazole
azo dye
dark brown
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 CH302394A publication Critical patent/CH302394A/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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 285138.    Verfahren zur Herstellung eines     Azofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Azofarbstoff    gelangt, wenn man       3-Methyl-5-pyrazolon    mit einer     Diazoverbin-          dung    kuppelt, die man erhält, wenn man       tetrazotiertes        4,4'-Diaminodiphenyl    einseitig  mit der     2-[4'-(8"-Oxynaphthyl-[2"]-aminophe-          nyl)    ] -     6-methy        lbenzthiazol-X',6"-disulfonsäure     kuppelt,

   in welcher die in     X'-Stellung    befind  liche     Sulfonsäuregruppe    dieselbe Stellung ein  nimmt wie die     Sulfonsäuregruppe    der durch  Sulfonieren von     2-(4'-Aminophenyl)-6-methyl-          benzthiazol    mittels konzentrierter Schwefel  säure erhältlichen     2-(4'-Aminophenyl)-6-me-          thylbenzthiazolsulfonsäure.     



  Der neue     Disazofarbstoff    bildet ein dunk  les Pulver, das sich in Wasser mit dunkel  brauner Farbe löst und die     Cellulosefaser    in       violettstichigen,    dunkelbraunen Tönen färbt,  die sich besonders durch gute Waschechtheit  auszeichnen.

      <I>Beispiel:</I>  18,4 4 Teile     4,4'-Diaminodiphenyl    werden  in üblicher Weise     tetrazotiert.    Die klare     Tetra-          zolösung    vereinigt man mit einer neutralen  Lösung von 55 Teilen     2-[4'-(8"-Oxynaphthyl-          [    2"]     -aminophenyl)    ]     -6-methylbenzthiazol-X,        6"-          disulfonsäure,    die mit 28 Teilen kristallisier  tem     Natriumacetat    versetzt wurde.

   Bei einer  Kupplungstemperatur von 10 bis 15  ist nach  4 bis 6 Stunden keine     Tetrazoverbindung    mehr  im Reaktionsgemisch nachweisbar. Die Zwi-         schenverbindung    wird nun mit einer     bicar-          bonatalkalischen    Lösung von 10 Teilen     3-Me-          thyl-5-pyrazolon    vermischt und nötigenfalls  durch     Zutropfen    von verdünnter     Natriumcar-          bonatlösung    ein     pH-Wert    von 7,0 bis 8,0 einge  halten. Die Kupplung verläuft langsam und  ist erst nach vielstündigem     Rühren    beendet.

    Durch Zugabe von     Natriumchlorid    zum er  wärmten Kupplungsgemisch wird der gebil  dete     Disazofarbstoff    abgeschieden und     abfil-          trier    t.



  <B> Additional patent </B> to main patent no. 285138. Process for the production of an azo dye. It has been found that a valuable azo dye is obtained when 3-methyl-5-pyrazolone is coupled with a diazo compound, which is obtained when tetrazotized 4,4'-diaminodiphenyl is unilaterally connected to the 2- [4'- (8 "-oxynaphthyl- [2"] - aminophenyl)] - 6-methy lbenzthiazol-X ', 6 "-disulfonic acid couples,

   in which the sulfonic acid group in the X'-position occupies the same position as the sulfonic acid group of 2- (4'-aminophenyl) obtainable by sulfonating 2- (4'-aminophenyl) -6-methylbenzthiazole using concentrated sulfuric acid 6-methylbenzothiazole sulfonic acid.



  The new disazo dye forms a dark powder that dissolves in water with a dark brown color and dyes the cellulose fiber in purple-tinged, dark brown shades, which are particularly characterized by good washfastness.

      <I> Example: </I> 18.4 4 parts of 4,4'-diaminodiphenyl are tetrazotized in the usual way. The clear tetrazole solution is combined with a neutral solution of 55 parts of 2- [4 '- (8 "-oxynaphthyl- [2"] -aminophenyl)] -6-methylbenzthiazole-X.6 "- disulfonic acid, which with 28 parts crystallized sodium acetate was added.

   At a coupling temperature of 10 to 15, no more tetrazo compounds can be detected in the reaction mixture after 4 to 6 hours. The intermediate compound is then mixed with a bicarbonate-alkaline solution of 10 parts of 3-methyl-5-pyrazolone and, if necessary, a pH of 7.0 to 8.0 is maintained by adding dropwise dilute sodium carbonate solution. The coupling proceeds slowly and is only complete after stirring for many hours.

    By adding sodium chloride to the heated coupling mixture, the disazo dye formed is deposited and filtered off.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Azofarb- stoffes, dadurch gekennzeichnet, dass man 3 Methyl-5-pyrazolon mit einer Diazoverbindung kuppelt, die man erhält, wenn man tetrazotier- tes 4,4'-Diaminodiphenyl einseitig mit der 2- [V- (8"- Oxynaphthyl - [2"] - aminophenyl) ] - 6 - methylbenzthiazol-X',6"-disulfonsäure kuppelt, PATENT CLAIM: Process for the production of an azo dye, characterized in that 3 methyl-5-pyrazolone is coupled with a diazo compound which is obtained when tetrazotized 4,4'-diaminodiphenyl on one side with the 2- [V- ( 8 "- Oxynaphthyl - [2"] - aminophenyl)] - 6 - methylbenzthiazol-X ', 6 "-disulfonic acid couples, in welcher die in X'-Stellung befindliche Sul- fonsäuregruppe dieselbe Stellung einnimmt wie die Sulfonsäuregruppe der durch Sulfonieren von 2-(4'-Aminophenyl)-6-methylbenzthiazol mittels konzentrierter Schwefelsäure erhältli chen 2-(4'-Aminophenyl)-6-methylbenzthiazol- sulfonsäure. Der neue Disazofarbstoff bildet ein dunk les Pulver, in which the sulfonic acid group in the X'-position occupies the same position as the sulfonic acid group of the 2- (4'-aminophenyl) -6- obtainable by sulfonating 2- (4'-aminophenyl) -6-methylbenzthiazole with concentrated sulfuric acid methylbenzthiazole sulfonic acid. The new disazo dye forms a dark powder, das sich in Wasser mit dunkel- brauner Farbe löst und die Cellulosefaser in violettstichigen, dunkelbraunen Tönen färbt, die sich besonders durch gute Waschechtheit auszeichnen. which dissolves in water with a dark brown color and dyes the cellulose fiber in purple-tinged, dark brown tones, which are particularly characterized by good washfastness.
CH302394D 1949-08-25 1952-02-12 Process for the preparation of an azo dye. CH302394A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH285138T 1949-08-25
CH302394T 1952-02-12

Publications (1)

Publication Number Publication Date
CH302394A true CH302394A (en) 1954-10-15

Family

ID=25732482

Family Applications (2)

Application Number Title Priority Date Filing Date
CH285138D CH285138A (en) 1949-08-25 1949-08-25 Process for the preparation of an azo dye.
CH302394D CH302394A (en) 1949-08-25 1952-02-12 Process for the preparation of an azo dye.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH285138D CH285138A (en) 1949-08-25 1949-08-25 Process for the preparation of an azo dye.

Country Status (1)

Country Link
CH (2) CH285138A (en)

Also Published As

Publication number Publication date
CH285138A (en) 1952-08-31

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