CH302049A - Process for the preparation of a disazo dye. - Google Patents

Process for the preparation of a disazo dye.

Info

Publication number
CH302049A
CH302049A CH302049DA CH302049A CH 302049 A CH302049 A CH 302049A CH 302049D A CH302049D A CH 302049DA CH 302049 A CH302049 A CH 302049A
Authority
CH
Switzerland
Prior art keywords
condensation
sulfonic acid
cyanuric
remaining
chlorine atom
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 CH302049A publication Critical patent/CH302049A/en

Links

Classifications

    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01JELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J25/00Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
    • H01J25/34Travelling-wave tubes; Tubes in which a travelling wave is simulated at spaced gaps
    • H01J25/36Tubes in which an electron stream interacts with a wave travelling along a delay line or equivalent sequence of impedance elements, and without magnet system producing an H-field crossing the E-field
    • H01J25/38Tubes in which an electron stream interacts with a wave travelling along a delay line or equivalent sequence of impedance elements, and without magnet system producing an H-field crossing the E-field the forward travelling wave being utilised
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/14Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Microwave Tubes (AREA)
  • Coloring (AREA)
  • Particle Accelerators (AREA)

Description

  

  Zusatzpatent zum Hauptpatent Nr. 298139.    Verfahren zur Herstellung eines     Disazofarbstoffes.     



  Es wurde gefunden, dass man zu einem wertvollen     Disazofarbstoff        gelangt,    w       die        Aminomonoazofarbstoffe    der Formeln  
EMI0001.0006     
    mittels     Cyanurehlorid    miteinander konden  siert und das noch verbleibende dritte an den       Cyanurring    gebundene Chloratom durch den  Rest der     Aminobenzol-3-sulfonsäure    ersetzt.  



  Der neue Farbstoff bildet ein gelbes Pul  ver, das sich in Wasser mit gelber Farbe löst  und     Baumwolle    und regenerierte     Cellulose    in  sehr reinen, gelben Tönen anfärbt. Nach dem  ein- oder     zweibadigen        Naehkupferungsverfah-          ren    erhält man gelbe Töne von sehr guter  Nass- und Lichtechtheit.  



  Die Vereinigung der beiden     Aminomono-          azofa.rbstoffe    mittels     Cyanurehlorid    und der  Ersatz des noch verbleibenden dritten an den       Cy        anurring    gebundenen Chloratoms durch  den Rest der     Aminobenzol-3-sulfonsäure    er  folgen zweckmässig in wässerigem, schwach  alkalischem Medium. Es empfiehlt sich, den    H-     Vert    und/oder die     Umsetzungstemperatur     P<B>N</B>  bei jeder Kondensationsstufe gegenüber der  vorhergehenden zu erhöhen.

           Beispiel:     Eine Lösung aus 49 Teilen     4'-(4"-Amino)-          b        enzoylamino    - 2' - chlor -     4-oxy-1,1'-azobenzol-3-          carbonsäure-5-sulfonsäure    und 10,6 Teilen Na  triumcarbonat in 2000 Teilen Wasser giesst  man bei 5      innert    10 Minuten zu einer     Auf-          schlämmung    von 18,4 Teilen     Cyanurchlorid     in wenig Eiswasser und neutralisiert die ent  stehende Salzsäure     mit    einer Lösung von 8,4  Teilen     Natriumbicarbonat    in 30 Teilen Was  ser.

   Nach eine Stunde ist die     Kondensation     beendet. Hierauf giesst man eine 40  warme  Lösung von 37,1 Teilen     4'-Amino-2'-ehlor-4-          oxy-1,1'-        azobenzol-3-carbonsäure-5-sulfonsäure         in 1000 Teilen Wasser zu und hält die Tem  peratur 12 Stunden unter gutem Rühren bei  30 bis 35 . Während dieser Zeit tropft man  die Lösung von 10 Teilen     Natriumbicarbonat     in 35 Teilen Wasser zu. Anschliessend giesst  man 37 Teile     Anilin-3-sulfonsäure    zu, erwärmt  2 Stunden auf $5 bis 90 , streut 10,6g Na-         triumcarbonat    zu und salzt das Kondensa  tionsprodukt mit     Natriumchlorid    aus.



  Additional patent to main patent No. 298139. Process for the production of a disazo dye.



  It has been found that a valuable disazo dye is obtained such as the amino monoazo dyes of the formulas
EMI0001.0006
    condensed with each other by means of cyanuric chloride and the remaining third chlorine atom bound to the cyanuric ring is replaced by the remainder of the aminobenzene-3-sulfonic acid.



  The new dye forms a yellow powder that dissolves in water with a yellow color and dyes cotton and regenerated cellulose in very pure, yellow tones. After the one or two bath sewing process, yellow shades of very good wet and light fastness are obtained.



  The combination of the two aminomonoazofa dyes by means of cyanuric chloride and the replacement of the remaining third chlorine atom bound to the cyano ring by the remainder of the aminobenzene-3-sulfonic acid are expediently carried out in an aqueous, weakly alkaline medium. It is advisable to increase the H-Vert and / or the reaction temperature P <B> N </B> in each condensation stage compared to the previous one.

           Example: A solution of 49 parts of 4 '- (4 "-amino) - b enzoylamino - 2' - chloro - 4-oxy-1,1'-azobenzene-3-carboxylic acid-5-sulfonic acid and 10.6 parts of sodium carbonate 2000 parts of water are poured at 5 within 10 minutes into a slurry of 18.4 parts of cyanuric chloride in a little ice water and the hydrochloric acid formed is neutralized with a solution of 8.4 parts of sodium bicarbonate in 30 parts of water.

   The condensation has ended after one hour. A warm solution of 37.1 parts of 4'-amino-2'-chloro-4-oxy-1,1'-azobenzene-3-carboxylic acid-5-sulfonic acid in 1000 parts of water is then poured in and the temperature is maintained 12 hours with good stirring at 30 to 35. During this time, the solution of 10 parts of sodium bicarbonate in 35 parts of water is added dropwise. 37 parts of aniline-3-sulfonic acid are then poured in, the mixture is heated to between $ 5 and 90 for 2 hours, 10.6 g of sodium carbonate are sprinkled in and the condensation product is salted out with sodium chloride.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Disazo- farbstoffes, dadurch gekennzeichnet, dass man die Aminomonoazofarbstoffe der Formeln EMI0002.0009 mittels Cyanurehlorid miteinander konden siert und das noch verbleibende dritte an den Cyanurring gebundene Chloratom durch den Rest der Aminobenzol-3-sulfonsäure ersetzt. Der neue Farbstoff bildet ein gelbes Pul ver, das sich in 'Wasser mit gelber Farbe löst und Baumwolle und regenerierte Cellulose in sehr reinen, gelben Tönen anfärbt. Claim: Process for the preparation of a disazo dye, characterized in that the aminomonoazo dyes of the formulas EMI0002.0009 condensed with each other by means of cyanuric chloride and the remaining third chlorine atom bound to the cyanuric ring is replaced by the remainder of the aminobenzene-3-sulfonic acid. The new dye forms a yellow powder that dissolves in water with a yellow color and dyes cotton and regenerated cellulose in very pure, yellow tones. Nach dem ein- oder zweibadigen Nachkupferungsverfah- ren erhält man gelbe Töne von sehr guter Nass- und Lichtechtheit. UNTERANSPRÜCHE: 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Konden sation mit Cyanurchlorid und den Ersatz des noch verbleibenden dritten an den Cyanur- ring gebundenen Chloratoms durch den 1test der Anilin-3-sulfonsäure in wässerigem, schwach alkalischem Medium und in der Weise durchführt, dass man den PH-Wert bei jeder Kondensationsstufe gegenüber der vorher gehenden erhöht. 2. After the one or two bath re-coppering process, yellow shades of very good wet and light fastness are obtained. SUBClaims: 1. The method according to claim, characterized in that the condensation with cyanuric chloride and the replacement of the remaining third chlorine atom bound to the cyanuric ring by the 1test of aniline-3-sulfonic acid in aqueous, weakly alkaline medium and in in such a way that the pH value is increased at each condensation stage compared to the previous one. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Konden sation mit Cyanurehlorid und den Ersatz des noch verbleibenden dritten an den Cva.nur- ring gebundenen Chloratoms durch den Rest der Anilin - 3 - sulfonsäure in wässerigem, schwach alkalischem Medium und in der Weise durehführt, dass man die Umsetzungstempera tur bei jeder Kondensationsstufe gegenüber der vorhergehenden erhöht. 3. Process according to claim, characterized in that the condensation with cyanuric chloride and the replacement of the remaining third chlorine atom bound to the Cva.nur- ring by the remainder of the aniline-3-sulfonic acid in an aqueous, weakly alkaline medium and in the manner dureheads that the reaction temperature is increased in each condensation stage compared to the previous one. 3. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Konden sation mit Cyanurchlorid und den Ersatz des noch verbleibenden dritten an den Cyanur- ring gebundenen Chloratoms durch den Rest der Anilin - 3 - sulfonsäure in wässerigem, schwach alkalischem Medium und in der Weise durchführt, dass man sowohl den pH-Wert als auch die Umsetzungstemperatur bei jeder Kondensationsstufe gegenüber der vorher gehenden erhöht. Process according to claim, characterized in that the condensation with cyanuric chloride and the replacement of the third remaining chlorine atom bound to the cyanuric ring with the remainder of the aniline-3-sulfonic acid is carried out in an aqueous, weakly alkaline medium and in the manner that both the pH and the reaction temperature are increased in each condensation stage compared to the previous one.
CH302049D 1949-11-08 1951-06-11 Process for the preparation of a disazo dye. CH302049A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB303049X 1949-11-08
GB2774869X 1949-11-08

Publications (1)

Publication Number Publication Date
CH302049A true CH302049A (en) 1954-09-30

Family

ID=26260377

Family Applications (2)

Application Number Title Priority Date Filing Date
CH302049D CH302049A (en) 1949-11-08 1951-06-11 Process for the preparation of a disazo dye.
CH298139D CH298139A (en) 1949-11-08 1951-06-11 Process for the preparation of a disazo dye.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH298139D CH298139A (en) 1949-11-08 1951-06-11 Process for the preparation of a disazo dye.

Country Status (3)

Country Link
US (1) US2774869A (en)
CH (2) CH302049A (en)
GB (1) GB671296A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2753481A (en) * 1952-06-14 1956-07-03 Sperry Rand Corp Travelling wave oscillators
US2981889A (en) * 1956-10-18 1961-04-25 Gen Electric Electron tube frequency multiplier of the traveling wave type

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL49857C (en) * 1935-11-30
NL62817C (en) * 1940-05-04
US2516944A (en) * 1947-12-18 1950-08-01 Philco Corp Impedance-matching device

Also Published As

Publication number Publication date
GB671296A (en) 1952-04-30
CH298139A (en) 1954-04-30
US2774869A (en) 1956-12-18

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