CH302018A - Process for the preparation of a vinyl sulfone dye. - Google Patents

Process for the preparation of a vinyl sulfone dye.

Info

Publication number
CH302018A
CH302018A CH302018DA CH302018A CH 302018 A CH302018 A CH 302018A CH 302018D A CH302018D A CH 302018DA CH 302018 A CH302018 A CH 302018A
Authority
CH
Switzerland
Prior art keywords
preparation
vinyl sulfone
dye
sulfone
bromovinyl
Prior art date
Application number
Other languages
German (de)
Inventor
Farbwerke Hoechst Akt Bruening
Original Assignee
Hoechst Ag
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 Hoechst Ag filed Critical Hoechst Ag
Publication of CH302018A publication Critical patent/CH302018A/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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves

Landscapes

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

Description

  

  Verfahren     zur        Herstellung    eines     Vinylsulfonfarbstoffes.       Gegenstand des vorliegenden Zusatzpaten  tes ist ein Verfahren zur Herstellung eines       Vinylsulfonfarbstoffes,    welches dadurch     ge-          kennzeiehnet    ist, dass man die     Diazoniumv        er-          bindLing    aus     1-Aminophenyl-3-(a-bromvinyl-          sulfon)    mit     1-(2'-Chlor-5'-sulfophenyl)-3-me-          thyl-5-py        razolon    kuppelt.  



  <I>Beispiel:</I>  7,86 Gewichtsteile     1-Aminophenyl-3-        (a-          bromvinylsulfon)    der Formel:  
EMI0001.0018     
    werden in salzsaurer Lösung mit 30     Volumtei-          1en        n-i\atriumnitritlösung        diazotiert.    Die     Di-          azolösung    lässt man bei 0-8  C in eine     Lösung     von 10,5 Gewichtsteilen     1-(2'-Chlor-5'-sulfo-          phenyl)-3-methyl-5-pyrazolon,

      30     Volumteilen          n-Natronlauge    und 7 Gewichtsteilen kristalli  siertem     Natriumacetat    in 150     Volumteilen     Wasser einfliessen. Durch Zusatz von kristalli  siertem     Natriumaeetat    wird dafür gesorgt, dass  das Reaktionsgemisch nicht kongosauer wird.  Nach beendeter Kupplung wird durch Erwär  men auf 40-50  C der Farbstoff in Lösung  gebracht. Durch Zugabe von     Kochsalz    wird  dann der Farbstoff der folgenden Formel:  
EMI0001.0034     
    abgeschieden, abgesaugt, mit Kochsalzlösung  neutral gewaschen     und        getrocknet.     



  Das so erhaltene Produkt stellt ein gelbes  Pulver dar, das Wolle     in    gelben Tönen von  guten     Echtheitseigenschaften.    färbt.  



  Das als     Diazokomponente    verwendete     1-          Aminophenyl    - 3 - (a -     bromv        inylsulfon)    kann  durch     Anlagerung    von Brom an     Phenyl-vinyl-          sulfon,        Abspaltung    von Bromwasserstoff,     Ni-          trierung    des     Pheriyl-a-bromvinylsulfons    in  schwefelsaurer     Lösung    und     'Reduktion    des     1-          Nitrophenyl-3-(a-bromvinylsulfons)    erhalten  werden.

   Das Amin schmilzt bei 94  C.



  Process for the preparation of a vinyl sulfone dye. The subject of the present additional patent is a process for the production of a vinyl sulfone dye, which is characterized in that the diazonium compounds are made from 1-aminophenyl-3- (a-bromovinyl sulfone) with 1- (2'-chloro 5'-sulfophenyl) -3-methyl-5-pyrazolone couples.



  <I> Example: </I> 7.86 parts by weight of 1-aminophenyl-3- (a-bromovinyl sulfone) of the formula:
EMI0001.0018
    are diazotized in hydrochloric acid solution with 30 parts by volume of n-i \ atrium nitrite solution. The diazo solution is left at 0-8 ° C. in a solution of 10.5 parts by weight of 1- (2'-chloro-5'-sulfophenyl) -3-methyl-5-pyrazolone,

      Pour 30 parts by volume of n-sodium hydroxide solution and 7 parts by weight of crystallized sodium acetate into 150 parts by volume of water. The addition of crystallized sodium acetate ensures that the reaction mixture does not become acidic to the Congo. After the coupling is complete, the dye is brought into solution by heating to 40-50 ° C. By adding table salt, the dye becomes the following formula:
EMI0001.0034
    deposited, filtered off with suction, washed neutral with sodium chloride solution and dried.



  The product obtained in this way is a yellow powder, the wool in yellow tones has good fastness properties. colors.



  The 1-aminophenyl - 3 - (a - bromovynylsulfon) used as a diazo component can be obtained by adding bromine to phenyl vinyl sulfone, splitting off hydrogen bromide, nitrating the pheriyl a-bromovinyl sulfone in a sulfuric acid solution and reducing the 1- Nitrophenyl-3- (a-bromovinyl sulfone) can be obtained.

   The amine melts at 94 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Vinylsul- fonfarbstoffes, dadurch gekennzeichnet, dass man die Diazoniumverbindung aus 1-Amino- phenyl-3-(a-bromvinylsulfon) mit 1-(2'-Chlor- 5'-sulfophenyl)-3-methyl-5-pyrazolon kuppelt. Das so erhaltene Produkt stellt ein gelbes Pulver dar, das Wolle in gelben Tönen von guten Echtheitseigenschaften färbt. PATENT CLAIM: Process for the production of a vinyl sulfon dye, characterized in that the diazonium compound is obtained from 1-aminophenyl-3- (a-bromovinyl sulfone) with 1- (2'-chloro-5'-sulfophenyl) -3-methyl- 5-pyrazolone couples. The product thus obtained is a yellow powder which dyes wool in yellow shades with good fastness properties.
CH302018D 1951-07-16 1951-07-16 Process for the preparation of a vinyl sulfone dye. CH302018A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH302018T 1951-07-16
CH296001T 1951-07-16

Publications (1)

Publication Number Publication Date
CH302018A true CH302018A (en) 1954-09-30

Family

ID=25733651

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302018D CH302018A (en) 1951-07-16 1951-07-16 Process for the preparation of a vinyl sulfone dye.

Country Status (1)

Country Link
CH (1) CH302018A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5231171A (en) * 1990-12-24 1993-07-27 Basf Aktiengesellschaft Reactive dyes having an allylsulfonyl or propargylesulfonyl group

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5231171A (en) * 1990-12-24 1993-07-27 Basf Aktiengesellschaft Reactive dyes having an allylsulfonyl or propargylesulfonyl group

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