CH247442A - Process for the preparation of a new yellow azo dye. - Google Patents

Process for the preparation of a new yellow azo dye.

Info

Publication number
CH247442A
CH247442A CH247442DA CH247442A CH 247442 A CH247442 A CH 247442A CH 247442D A CH247442D A CH 247442DA CH 247442 A CH247442 A CH 247442A
Authority
CH
Switzerland
Prior art keywords
azo dye
new
preparation
parts
dye
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH247442A publication Critical patent/CH247442A/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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/001—Dyes containing an onium group attached to the dye skeleton via a bridge
    • C09B69/005—Isothiuronium group
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/54—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an epoxy or halohydrin group
    • C09B62/58—Azo dyes

Landscapes

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

Description

  

      Verfahren    zur Herstellung eines neuen     gelben        Azofarbstoffes.       Die vorliegende Erfindung betrifft     ein     Verfahren zur Herstellung eines     neuen,    gel  ben     Azofarbstoffes    und ist dadurch gekenn  zeichnet,     da3        Di-(chlormethyl)-4,4'-di-(6-          methylbenzthiazyl-2)-azobenzol    mit     Pyridin          unter    Bildung eines     quaternären    Ammonium  salzes erhitzt wird.  



  Der neue Farbstoff ist einhellgelbes Pul  ver, welches sich in Wasser unter Bildung  einer gelben Lösung löst, welche Baumwolle  in hellgelben Tönen von guten Echtheits  eigenschaften gegen Waschen und Kochen in  Soda an der Luft anfärbt.  



  <I>Beispiel:</I>  12 Teile     Di-(chlormethyl)-4,4'-di-(6-me-          thylbenzthiazyl-2)-azobenzol    (hergestellt     wie     weiter unten beschrieben) werden mit 150  Teilen     Pyridin    gemischt. Die erhaltene Sus  pension wird während 10 Minuten gekocht,  wobei sie in hellgelb umschlägt, sobald das       quaternäre        Ammoniums-alz    erzeugt wird.  Nach dem Verdünnen mit dem doppelten  Volumen Aceton wird die     Suspension    ab  filtriert und der Filterkuchen mit Aceton ge  waschen, um das     Pyridin    zu entfernen.  Schliesslich wird an der Luft getrocknet.

   Das  neue     quaternäre        Ammoniumsalz    stellt ein  hellgelbes Pulver dar.  



  Das     verwendete        Di-chlormethyl-4,4'-di-          (6-methylbenzthiazyl-2)-azobenzol    wird wie  folgt erhalten: 10 Teile     4,4'-Di-(6-methyl-          benzthiazyl-2)-azobenzol    werden     in    150  Teilen 100     %        iger    Schwefelsäure unterhalb         30     C gelöst und     mit    50 Teilen     sym.        Di-          chlorcU#methyläther    versetzt. Das Gemisch  wird rasch auf 60  C :erhitzt und bei dieser  Temperatur während 20     Minuten    gehalten.

    Die :erhaltene rote Lösung wird auf 100 Teile  eines     Eis-Wassergemisches    gegossen, filtriert  und der Filterkuchen mit Wasser säurefrei  gewaschen. Das Produkt wird an der Luft  getrocknet. 12 Teile eines     blassgelben    Pul  vers werden     erhalten.     



  Man stellt     ein    Färbebad her, indem man  1 Teil des so erhaltenen Farbstoffes in 1500  Teilen Wasser löst. 50 Teile gebleichten  Baumwollgarns werden in das Färbebad ein  geführt. Nun wird die Temperatur auf 60  C  erhöht und gehalten. Man versetzt bei<B>60'C</B>  dreimal nach je 10     Minuten    mit 1 Teil Soda  asche. Das Baumwollgarn wird gelegentlich  gewendet. Das Färbebad wird während wei  teren 15     Minuten    auf 60  C gehalten. Schliess  lich wird die Baumwolle     herausgenommen,     mit Wasser gespült und getrocknet.

   Das  Baumwollgarn weist einen hellgelben Farb  ton auf, wobei die Färbung sich durch     gute          Echtheitseigenschaften    gegen Waschen und  Kochen in Soda an der Luft     auszeichnet.    Die  Echtheit ähnelt derjenigen von Färbungen,  welche mit     Caledon    Gelb G     (Colour    Index  Nr. 1118)     erhalten    werden.



      Process for the preparation of a new yellow azo dye. The present invention relates to a process for the production of a new, yellow azo dye and is characterized in that di- (chloromethyl) -4,4'-di- (6-methylbenzthiazyl-2) -azobenzene with pyridine to form a quaternary ammonium salt is heated.



  The new dye is a light yellow powder which dissolves in water to form a yellow solution which stains cotton in light yellow tones with good fastness properties against washing and boiling in soda in the air.



  <I> Example: </I> 12 parts of di- (chloromethyl) -4,4'-di- (6-methylbenzthiazyl-2) -azobenzene (prepared as described below) are mixed with 150 parts of pyridine. The suspension obtained is boiled for 10 minutes, turning light yellow as soon as the quaternary ammonium salt is generated. After diluting with twice the volume of acetone, the suspension is filtered off and the filter cake is washed with acetone in order to remove the pyridine. Finally, it is air-dried.

   The new quaternary ammonium salt is a light yellow powder.



  The di-chloromethyl-4,4'-di- (6-methylbenzthiazyl-2) -azobenzene used is obtained as follows: 10 parts of 4,4'-di- (6-methylbenzthiazyl-2) -azobenzene are obtained in 150 Parts of 100% sulfuric acid dissolved below 30 ° C. and mixed with 50 parts of symmetrical dichlorocU # methyl ether. The mixture is heated rapidly to 60 ° C. and held at this temperature for 20 minutes.

    The red solution obtained is poured onto 100 parts of an ice-water mixture, filtered and the filter cake is washed acid-free with water. The product is air dried. 12 parts of a pale yellow powder are obtained.



  A dye bath is prepared by dissolving 1 part of the dye thus obtained in 1500 parts of water. 50 parts of bleached cotton yarn are introduced into the dye bath. The temperature is now increased to 60 ° C. and maintained. At <B> 60'C </B>, 1 part of soda ash is added three times every 10 minutes. The cotton yarn is turned occasionally. The dyebath is kept at 60 ° C. for 15 more minutes. Finally the cotton is removed, rinsed with water and dried.

   The cotton yarn has a light yellow shade, the dyeing being characterized by good fastness properties to washing and boiling in soda in the air. The fastness is similar to that of dyeings obtained with Caledon Yellow G (Color Index No. 1118).

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen, gelben Azofarbstoffes, dadurch gekennzeich- rnet, dass Di-(chlormethyl)-4,4'-di-(6-methyl- benzthiazyl-2)-azobenzol mit Pyridin unter Bildung eines quaternären Ammoniumsalzes erhitzt wird. PATENT CLAIM: Process for the production of a new, yellow azo dye, characterized in that di- (chloromethyl) -4,4'-di- (6-methylbenzthiazyl-2) -azobenzene is heated with pyridine to form a quaternary ammonium salt . Der neue Farbstoff ist ein hellgelbes Pul ver, welches sich in Wasser unter Bildung einer gelben Lösung löst, welche Baumwolle in hellgelben Tönen von guten Echtheits eigenschaften gegen Waschen und Kochen in Soda an der Luft anfärbt. The new dye is a light yellow powder which dissolves in water to form a yellow solution which stains cotton in light yellow tones with good fastness properties against washing and boiling in soda in the air.
CH247442D 1944-05-08 1945-05-07 Process for the preparation of a new yellow azo dye. CH247442A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB247442X 1944-05-08

Publications (1)

Publication Number Publication Date
CH247442A true CH247442A (en) 1947-03-15

Family

ID=10216566

Family Applications (2)

Application Number Title Priority Date Filing Date
CH247442D CH247442A (en) 1944-05-08 1945-05-07 Process for the preparation of a new yellow azo dye.
CH252479D CH252479A (en) 1944-05-08 1945-05-07 Process for the preparation of a new yellow azo dye.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH252479D CH252479A (en) 1944-05-08 1945-05-07 Process for the preparation of a new yellow azo dye.

Country Status (1)

Country Link
CH (2) CH247442A (en)

Also Published As

Publication number Publication date
CH252479A (en) 1947-12-31

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