CH302045A - Process for the preparation of a disazo dye. - Google Patents

Process for the preparation of a disazo dye.

Info

Publication number
CH302045A
CH302045A CH302045DA CH302045A CH 302045 A CH302045 A CH 302045A CH 302045D A CH302045D A CH 302045DA CH 302045 A CH302045 A CH 302045A
Authority
CH
Switzerland
Prior art keywords
phosgene
preparation
disazo dye
dyes
good
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 CH302045A publication Critical patent/CH302045A/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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Zusatzpatent    zum Hauptpatent Nr. 298138.         Verfahren    zur Herstellung eines     Disazofarbstoffes.       Es wurde gefunden, dass man zu einem  wertvollen     Disazofarbstoff    gelangt, wenn man  die Farbstoffe der Formeln  
EMI0001.0005     
  
EMI0001.0006     
    mittels     Phosgen    zum     Harnstoffderivat    ver  einigt.  



  Der neue Farbstoff bildet ein braunes<B>Pul-</B>  ver, das sich in Wasser mit oranger Farbe  löst und Baumwolle und regenerierte     Cellulose     in schönen gelben Tönen von guter Nass- und  Lichtechtheit und sehr guter neutraler und  alkalischer     Ätzbarkeit    färbt. Nach dem     ein-          oder        zweibadigen        Nachkupferungsverfahren     erhält man etwas rötere Töne von sehr guter       @T    ass- und Lichtechtheit.  



  Die Vereinigung der beiden     Aminomono-          azofarbstoffe    zum asymmetrischen Harnstoff  deriva.t mittels     Phosgen    erfolgt zweckmässig  in wässerigem, schwach alkalischem, z. B.       alkalicarbonatalkalischem,    Medium bei leicht  erhöhter Temperatur in Gegenwart einer Puf  fersubstanz, wie beispielsweise     Natriumacetat.     Der für die Reaktion günstige     pH-Wert    liegt  zwischen 9,5     \und    5,5.

      <I>Beispiel:</I>  17,25 Teile     1-Amino-2-chlor-4-nitrobenzol     werden in bekannter Weise     diazotiert        und    mit  13,8 Teilen     1-Oxybenzol-2-carbonsäure    in  schwach alkalischer Lösung gekuppelt. Hier  auf lässt man eine Lösung von 9,2 Teilen     Na-          triumsulfhydrat    in 50 Teilen Wasser zuflie  ssen und rührt bei 60 bis 70 , bis die Reduk  tion der Nitrogruppe beendet ist.  



  29,1 Teile des abgeschiedenen und getrock  neten     Aminoazofarbstoffes    oder eine entspre  chende Menge Filterpaste werden mit 36,5 Tei  len     4-Amino-2,5-dimethyl-4'-oxy-1,1'-azoben-          zol-3'-carbonsäure-5'-sulfonsäure    unter Zusatz  von     Natriumcarbonat    bis zur deutlich alkali  schen Reaktion in 2000 Teilen Wasser gelöst  und bei 35 bis 40  in Gegenwart von Natrium  acetat als     säurebindendes    Mittel so lange unter  häufigem Ersatz des verbrauchten     Natrium-          carbonats    mit     Phosgen    behandelt, bis keine       Aminogruppe    mehr nachgewiesen werden  kann.

   Der vollständig ausgeschiedene Farb  stoff wird filtriert und     -cetrocknet.  



      Additional patent to main patent No. 298138. Process for the production of a disazo dye. It has been found that a valuable disazo dye is obtained by using the dyes of the formulas
EMI0001.0005
  
EMI0001.0006
    united by means of phosgene to form the urea derivative.



  The new dye forms a brown <B> powder </B> which dissolves in water with an orange color and dyes cotton and regenerated cellulose in beautiful yellow tones with good wet and light fastness and very good neutral and alkaline etchability. After the one or two bath post-copper plating process, you get slightly redder tones of very good @Tass and lightfastness.



  The combination of the two amino monoazo dyes to form the asymmetrical urea deriva.t by means of phosgene is expediently carried out in aqueous, weakly alkaline, e.g. B. alkaline carbonate alkaline medium at a slightly elevated temperature in the presence of a Buf fersubstanz such as sodium acetate. The pH value favorable for the reaction is between 9.5 and 5.5.

      <I> Example: </I> 17.25 parts of 1-amino-2-chloro-4-nitrobenzene are diazotized in a known manner and coupled with 13.8 parts of 1-oxybenzene-2-carboxylic acid in a weakly alkaline solution. A solution of 9.2 parts of sodium sulfhydrate in 50 parts of water is allowed to flow in here and the mixture is stirred at 60 to 70 until the reduction of the nitro group has ended.



  29.1 parts of the separated and getrock designated aminoazo dye or a corresponding amount of filter paste are mixed with 36.5 parts of 4-amino-2,5-dimethyl-4'-oxy-1,1'-azoben- zol-3'- carboxylic acid-5'-sulfonic acid with the addition of sodium carbonate until the clearly alkaline reaction is dissolved in 2000 parts of water and treated with phosgene at 35 to 40 in the presence of sodium acetate as an acid-binding agent, frequently replacing the used sodium carbonate, until none Amino group can be detected more.

   The completely separated dye is filtered and dried.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Disazo- farbstoffes, dadurch gekennzeichnet, dass man die Farbstoffe der Formeln EMI0001.0041 und EMI0002.0001 mittels Phosgen zum Harnstoffderivat ver einigt. Der neue Farbstoff bildet ein braunes Pul ver, das sieh in Wasser mit oranger Farbe löst und Baumwolle und regenerierte Cellulose in schönen gelben Tönen von guter Nass- und Lichtechtheit und sehr guter neutraler und alkalischer Ätzbarkeit färbt. PATENT CLAIM: Process for the preparation of a disazo dye, characterized in that the dyes of the formulas EMI0001.0041 and EMI0002.0001 united by means of phosgene to form the urea derivative. The new dye forms a brown powder that dissolves in water with an orange color and dyes cotton and regenerated cellulose in beautiful yellow shades of good wet and light fastness and very good neutral and alkaline etchability. Nach dem ein- oder zweibadigen Nachkupferungsverfahren erhält man etwas rötere Töne von sehr guter Nass- und Lichtechtheit. UNTERANSPRUCH Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man die Behand lung mit Phosgen in wässerigem Medium bei einem pH-Wert durchführt, der zwischen 9,5 und 5,5 liegt. After the one or two bath re-coppering process, slightly redder tones with very good wet and light fastness are obtained. SUBCLAIM Method according to claim, characterized in that the treatment with phosgene is carried out in an aqueous medium at a pH between 9.5 and 5.5.
CH302045D 1951-05-25 1951-05-25 Process for the preparation of a disazo dye. CH302045A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH302045T 1951-05-25
CH298138T 1951-05-25

Publications (1)

Publication Number Publication Date
CH302045A true CH302045A (en) 1954-09-30

Family

ID=25733944

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302045D CH302045A (en) 1951-05-25 1951-05-25 Process for the preparation of a disazo dye.

Country Status (1)

Country Link
CH (1) CH302045A (en)

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