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CH298139A - Process for the preparation of a disazo dye. - Google Patents

Process for the preparation of a disazo dye.

Info

Publication number
CH298139A
CH298139A CH298139DA CH298139A CH 298139 A CH298139 A CH 298139A CH 298139D A CH298139D A CH 298139DA CH 298139 A CH298139 A CH 298139A
Authority
CH
Switzerland
Prior art keywords
yellow
parts
phosgene
dye
dyes
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 CH298139A publication Critical patent/CH298139A/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

  

  Verfahren zur Herstellung eines     Disazofarbstoffes.       Es wurde gefunden,     dass    man zu einem wertvollen     Disazolarbstoff    gelangt, wenn man       die.Aminoinonoazofarbstoffe    der Formeln  
EMI0001.0005     
    mittels     Phosgen    zum     Harnstoffderivat    ver  einigt.  



  Der neue Farbstoff bildet ein gelbbraunes  Pulver, das sich in Wasser mit gelber Farbe,  löst und Baumwolle und regenerierte     Cellulose     in leuchtend     grünstichig    gelben Tönen     *von     guter     Nass-    und Lichtechtheit anfärbt. Nach  dem ein- oder     zweibadigen        Nachkupferungs-          verfahren    erhält man     grünstichig    gelbe Töne  von hoher Reinheit und sehr guter     Nass-    und  Lichtechtheit.  



  Die Vereinigung der beiden     Aminomono-          azofarbstoffe    zum asymmetrischen     Harnstoff-          derivat    mittels     Phosgen    erfolgt zweckmässig  in     wässrigem,    schwach alkalischem, z.

   B.     alka-          licarbonatalkalischem    Medium bei leicht er  höhter Temperatur in Gegenwart einer Puffer  substanz, wie beispielsweise     Natriumacetat.     Der für die Reaktion günstige     pH7Wert    liegt  zwischen     9,5    und     5,5.       <I>Beispiel:</I>    <B>17,25</B> Teile     1-Amino-2-chlor-4-nitrobenzol     werden in bekannter Weise     diazotiert    und mit  <B>13,8</B> Teilen     1-Oxybenzol-2-earbonsäure    in  schwach saurer bis alkalischer Lösung gekup  pelt.  



  <B>32,15</B> Teile des     aIgeschiedenen    und getrock  neten Farbstoffes werden in 120 Teilen rau  chende Schwefelsäure mit einem Gehalt an  freiem     Anhydrid    von '20     %    eingetragen     und-          unter    gutem Rühren<B>10</B> Stunden auf<B>95</B> bis       10011    erhitzt. Nach dem Erkalten -wird die  Reaktionsmasse auf Eis ausgetragen, einige  Stunden gerührt und filtriert. Die     Farbstoff-          paste    wird in<B>350</B> Teilen heissem Wasser ge  löst und filtriert, wobei ein kleiner Teil     un-          sulfonierten    Farbstoffes auf dem Filter bleibt.

    Das Filtrat wird mit<B>30</B>     %        iger        Natrium-          hydroxydlösung    versetzt, bis alkalische Reak  tion auf Brillantgelb eintritt und das Natrium-      salz des Farbstoffes mit     Natriumchlorid    ge  fällt.  



  Die     Parbstoffpaste    wird in<B>500</B> Teilen  Wasser gelöst und die Nitrogruppe mit<B>9,2</B>  Teilen     Natriumsulihydrat    bei<B>60</B> bis     7011    in die       Aminogruppe    übergeführt, der     Aminoazofarb-          stoff    mit     Natri-Lunehlorid    abgeschieden und fil  triert.  



  Zu der in<B>800</B>     Teil-en    Wasser gelösten     Farb-          stoffpaste    gibt man<B>16</B> Teile wasserfreies     Na-          triumearbonat    und     lässt    dann bei 40 bis     5011     <B>26</B> Teile     p-Nitrobenzoylehlorid,    in<B>50</B> Teilen  Aceton gelöst, zufliessen. Nachdem die Konden  sation beendet ist, wird der ausgefallene  Farbstoff filtriert Lind die Nitrogruppe wie  üblich mit     Natriumsullid    bei etwa<B>60</B> bis     6511     in die     Aminogruppe    übergeführt.

      49 Teile des     abgesehiedenen    und getrock  neten Farbstoffes, oder eine entsprechende  Menge     Farbstoffpaste    und<B>37,1</B> Teile     4-Amino-          2-chlor   <B>-</B>     4'-        oxy-1,1'-azobenzol-3'-earbonsäiire-5'-          sulionsä-Lire    werden in bekannter Weise in Ge  genwart von     Natriumearbonat    als säurebinden  dem Mittel und     Natriumaeetat    als Puffer  substanz mit     Phosgen    behandelt, bis keine       Aminogruppe    mehr nachweisbar ist. Der voll  ständig ausgefallene Farbstoff wird filtriert  und getrocknet.



  Process for the preparation of a disazo dye. It has been found that a valuable disazolar material is obtained by using the aminoinonoazo dyes of the formulas
EMI0001.0005
    united by means of phosgene to form the urea derivative.



  The new dye forms a yellow-brown powder that dissolves in water with a yellow color and dyes cotton and regenerated cellulose in bright greenish yellow tones * with good wet and lightfastness. After the one or two bath re-coppering process, greenish yellow shades of high purity and very good wet and light fastness are obtained.



  The combination of the two amino monoazo dyes to form the asymmetric urea derivative by means of phosgene is expediently carried out in an aqueous, weakly alkaline, e.g.

   B. alkali carbonate alkaline medium at a slightly elevated temperature in the presence of a buffer substance such as sodium acetate. The pH value favorable for the reaction is between 9.5 and 5.5. <I> Example: </I> <B> 17.25 </B> parts of 1-amino-2-chloro-4-nitrobenzene are diazotized in a known manner and <B> 13.8 </B> parts 1 -Oxybenzene-2-carboxylic acid in weakly acidic to alkaline solution gekup pelt.



  32.15 parts of the separated and dried dye are added to 120 parts of fuming sulfuric acid with a free anhydride content of 20% and for 10 hours with thorough stirring Heated <B> 95 </B> to 10011. After cooling, the reaction mass is poured onto ice, stirred for a few hours and filtered. The dye paste is dissolved in <B> 350 </B> parts of hot water and filtered, with a small part of the unsulfonated dye remaining on the filter.

    <B> 30 </B>% sodium hydroxide solution is added to the filtrate until an alkaline reaction to brilliant yellow occurs and the sodium salt of the dye precipitates with sodium chloride.



  The paraffin paste is dissolved in <B> 500 </B> parts of water and the nitro group is converted into the amino group with <B> 9.2 </B> parts of sodium sulphate at <B> 60 </B> to 7011, the aminoazo color The substance is separated and filtered with sodium chloride.



  <B> 16 </B> parts of anhydrous sodium carbonate are added to the dye paste dissolved in <B> 800 </B> parts of water and then <B> 26 </B> parts are left at 40 to 5011 p-Nitrobenzoyl chloride, dissolved in <B> 50 </B> parts of acetone, flow in. After the condensation has ended, the precipitated dye is filtered and the nitro group is converted into the amino group as usual with sodium sulphide at about 60 to 6511.

      49 parts of the separated and dried dye, or a corresponding amount of dye paste and <B> 37.1 </B> parts of 4-amino-2-chloro <B> - </B> 4'- oxy-1,1 ' -azobenzene-3'-earbonsäiire-5'-sulionsä-Lire are treated in a known manner in the presence of sodium carbonate as the acid-binding agent and sodium acetate as a buffer substance with phosgene until no amino group can be detected. The completely precipitated dye is filtered and dried.

 

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines Disazo- larbstoffes, dadurch gekennzeichnet, dass man die Aminomonoazofarbstoffe der Formeln EMI0002.0035 mittels Phosgen zum Harnstoffderivat ver einigt. Der neue Farbstoff bildet ein gelbbraunes Pulver, das sich in Wasser mit gelber Farbe löst und Baumwolle und regenerierte Cell-Li- lose in leuchtend grünstichig gelben Tönen von guter Nass- und Lichteehtheit anfärbt. <B> PATENT CLAIM: </B> Process for the production of a disazolar material, characterized in that the aminomonoazo dyes of the formulas EMI0002.0035 united by means of phosgene to form the urea derivative. The new dye forms a yellow-brown powder which dissolves in water with a yellow color and dyes cotton and regenerated cell-lilos in bright greenish yellow tones with good wetness and lightness. Nach dem ein- oder zweibadigen Nachkupferungs- verfahren erhält man grünstichig gelbe Töne von hoher Reinheit und sehr guter Nass- und Lichtechtheit. UNTERANSPRUCI-I: Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Behand lung mit Phosgen in wässrigein Medium bei einem pH-Wert durchführt, der zwischen<B>9,5</B> und<B>5,5</B> liegt. After the one or two bath re-coppering process, greenish yellow shades of high purity and very good wet and light fastness are obtained. SUB-CLAIM-I: Process according to patent claim, characterized in that the treatment with phosgene is carried out in an aqueous medium at a pH between <B> 9.5 </B> and <B> 5.5 </ B> lies.
CH298139D 1949-11-08 1951-06-11 Process for the preparation of a disazo dye. CH298139A (en)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number Publication Date
CH298139A true CH298139A (en) 1954-04-30

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 Before (1)

Application Number Title Priority Date Filing Date
CH302049D CH302049A (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
CH302049A (en) 1954-09-30
US2774869A (en) 1956-12-18
GB671296A (en) 1952-04-30

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