CH276907A - Process for the preparation of an azo dye of the stilbene series. - Google Patents

Process for the preparation of an azo dye of the stilbene series.

Info

Publication number
CH276907A
CH276907A CH276907DA CH276907A CH 276907 A CH276907 A CH 276907A CH 276907D A CH276907D A CH 276907DA CH 276907 A CH276907 A CH 276907A
Authority
CH
Switzerland
Prior art keywords
azo dye
mol
condensation
stilbene series
carried out
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 CH276907A publication Critical patent/CH276907A/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
    • C09B56/00—Azo dyes containing other chromophoric systems
    • C09B56/04—Stilbene-azo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Ziisatzpatent        zum    Hauptpatent     Nr.    274240.    Verfahren zur Herstellung eines     Azofarbstoffes    der     Stilbenreihe.       Es wurde gefunden,     dass    man zu einem  wertvollen     Azofarbstoff    der     Stilbenreihe    ge  langt, wenn man<B>1</B>     Mol        4,4#-Dinitrostilben-2,-')'-          disulfonsäure    mit<B>1</B> -.Hol des durch Kuppeln  von     diazotierter        1-Aniinonaphthalin-5-sulfoii-          säure    mit     1,

  3-Diaminobenzol    in     essi",saurem     Medium erhältlichen     Aminomonoazolarbstof-          fes    kondensiert.  



       Der    neue Farbstoff bildet ein dunkles Pul  ver, das sieh in Wasser mit brauner Farbe  löst. Er färbt Chromleder in satten, rotbrau  nen Tönen.  



  Die Kondensation der     4,4'-Dinitrostilben-          2,2'-disulfonsäure    wird zweckmässig in     wässe-          ri,-em    -Medium und in Gegenwart von     Alkali-          hydroxyd    durchgeführt.

   Hierbei werden die       ii;iteinander        umcz'usetzenden    Ausgangsstoffe       mit        Vorteil        in        verdünnter,        z.        B.        2-        bis   <B>8</B>     %in-er          Alkalilivdroxydlösung    während längerer Zeit,  beispielsweise fünf bis zwanzig Stunden bei  erhöhter Temperatur, z.

   B. in offenem Gefäss  bei Siedetemperatur des Reaktionsgemisches       und    unter     Rüekilusskfihlun,-,    oder bei noch  höheren Temperaturen und -unter Druck auf  einander einwirken gelassen.  



  <I>Beispiel:</I>  34,1 Teile<B>(0,1</B>     THol)    des     Monoazofarbstof-          fes,    der durch Kuppeln von     diazotierter          1-Aininonaphthalin-5-sulionsäure    mit     1,3-1)i-          aminobenzol    in     essiYsaurem    Medium erhalten  wird, werden mit 43,0 Teilen<B>(0,1</B>     Mol)        4,4'-Di-          iiitrostilben-2,

  2'-disulfonsäure    in<B>500</B> Teilen       Wasser        unter        Zusatz        von        50        Teilen        30%iger          Natriumhvdroxydlösung    warm gelöst und  dann unter Rühren     und        Rückflusskühlung       fünfzehn Stunden zum Sieden erhitzt.

   Dem  erkalteten Reaktionsgemisch werden<B>50</B> Teile       Natriumehlorid    zugegeben und durch Zusatz  von so viel Salzsäure das     übersehüssige        Na-          friumhydroxyd    so weit neutralisiert, bis     Bril-,          lantgelbpapier    noch schwach     oran-e    verfärbt  wird. Das Kondensationsprodukt ist praktisch  vollständig abgeschieden und kann     abfiltriert     und     getroeknet    werden.



      Additional patent to main patent No. 274240. Process for the production of an azo dye of the stilbene series. It has been found that a valuable azo dye of the stilbene series is obtained if <B> 1 </B> mol of 4,4 # -dinitrostilbene-2, - ')' - disulfonic acid with <B> 1 </B> -.Hol des by coupling of diazotized 1-aniinonaphthalene-5-sulfoii- acid with 1,

  3-diaminobenzene in essi ", acidic medium available aminomonoazolar substance condensed.



       The new dye forms a dark powder that dissolves in water with a brown color. It colors chrome leather in rich, red-brown tones.



  The condensation of 4,4'-dinitrostilbene-2,2'-disulfonic acid is expediently carried out in an aqueous medium and in the presence of alkali metal hydroxide.

   Here, the starting materials which react with one another are advantageously in dilute, e.g. B. 2- to <B> 8 </B>% in-er Alkalilivdroxydlösung for a long time, for example five to twenty hours at an elevated temperature, e.g.

   B. in an open vessel at the boiling point of the reaction mixture and under Rüekilusskfihlun, -, or at even higher temperatures and under pressure allowed to act on each other.



  <I> Example: </I> 34.1 parts <B> (0.1 </B> THol) of the monoazo dye obtained by coupling diazotized 1-ainonaphthalene-5-sulionic acid with 1.3-1) i-aminobenzene is obtained in acidic medium, 43.0 parts (0.1 mol) 4,4'-di-iitrostilben-2,

  2'-disulfonic acid dissolved in 500 parts of water with the addition of 50 parts of 30% sodium hydroxide solution and then heated to the boil for fifteen hours while stirring and refluxing.

   <B> 50 </B> parts of sodium chloride are added to the cooled reaction mixture and the excess sodium hydroxide is neutralized by adding sufficient hydrochloric acid until the brilliant yellow paper is still slightly orange in color. The condensation product is practically completely separated and can be filtered off and dried.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines Azofarb- stoffes der Stilbenreihe, dadurch gekennzeieh- riet, dass man<B>1</B> Mol 4,4-Dinitrostilben-2,2-di- sulfonsäure mit<B>1</B> Mol des durch Kuppeln von diazotierter 1-Aminoiiaphthalin-5-sulfonsäure mit 1.,3-Diaminobenzol in essigsaurem Medium erhältlichen Aminomonoazolarbstoffes kon densiert. <B> PATENT CLAIM: </B> Process for the production of an azo dye of the stilbene series, characterized in that <B> 1 </B> mol 4,4-dinitrostilbene-2,2-disulfonic acid is mixed with < B> 1 </B> mol of the aminomonoazolar material obtainable by coupling diazotized 1-Aminoiiaphthalin-5-sulfonic acid with 1., 3-diaminobenzene in an acetic acid medium condenses. Der neue Farbstoff bildet ein dunkles Pul ver, das sieh in Wasser mit brauner Farbe löst. Er färbt Chromleder in satten, rotbrau nen Tönen. UNTERANSPRMIE: <B>1..</B> Verfahren gemäss Patentansprueh, da- dureh gekennzeiehnet, dass man die Konden sation in wässerigem Medium und in Gegen- -#vart von Alkalihydroxyd durehführt. <B><U>9.</U></B> Verfahren gemäss Patentansprueh und Unteranspruch<B>1,</B> dadurch gekennzeichnet, The new dye forms a dark powder that dissolves in water with a brown color. It colors chrome leather in rich, red-brown tones. SUBSTANTIAL CLAIM: <B> 1 .. </B> Process according to patent claim, characterized in that the condensation is carried out in an aqueous medium and in the presence of alkali hydroxide. <B><U>9.</U> </B> Method according to patent claim and dependent claim <B> 1, </B> characterized in that, dass man die Kondensation durch Erhitzen der miteinander umzusetzenden Ausgangs stoffe während längerer Zeit in verdünnter Alkalihydroxvdlösung durchführt. that the condensation is carried out by heating the starting materials to be reacted with one another for a long time in dilute alkali metal hydroxide solution.
CH276907D 1949-02-04 1949-02-04 Process for the preparation of an azo dye of the stilbene series. CH276907A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH276907T 1949-02-04
CH274240T 1949-12-13

Publications (1)

Publication Number Publication Date
CH276907A true CH276907A (en) 1951-07-31

Family

ID=25731529

Family Applications (1)

Application Number Title Priority Date Filing Date
CH276907D CH276907A (en) 1949-02-04 1949-02-04 Process for the preparation of an azo dye of the stilbene series.

Country Status (1)

Country Link
CH (1) CH276907A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4742162A (en) * 1981-05-18 1988-05-03 Ciba-Geigy Corporation Azo-stibene condensates as leather dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4742162A (en) * 1981-05-18 1988-05-03 Ciba-Geigy Corporation Azo-stibene condensates as leather dyes

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