CH302019A - Process for the preparation of a vinyl sulfone dye. - Google Patents

Process for the preparation of a vinyl sulfone dye.

Info

Publication number
CH302019A
CH302019A CH302019DA CH302019A CH 302019 A CH302019 A CH 302019A CH 302019D A CH302019D A CH 302019DA CH 302019 A CH302019 A CH 302019A
Authority
CH
Switzerland
Prior art keywords
vinyl sulfone
preparation
vinyl
amino
methylbenzene
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 CH302019A publication Critical patent/CH302019A/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)
  • 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-          kennzeichnet    ist, dass man die Diazoniumver-         bindung    aus     1-Amino-4-methylbenzol-3-sulfon-          säure-        (2'-methoxy-5'-vinylsulfonyl)-phenyl-          amid    mit     1-(6'-Chlor-2'-methyl-4'-sulfophe-          nyl)

  -3-methyl-5-pyrazolon        kuppelt.            Beispiel:     3,8 Gewichtsteile     1-Amino-4-methylbenzol-3-sulfonsäure-(2'-methoxy-5'-vinylsulfonyl)-          phenylamid    der folgenden Formel:

    
EMI0001.0017     
    werden in salzsaurer Lösung mit 10 Volum-    teilen     n-Natriumnitritlösung    in üblicher Weise  diazotig     #t.    Die     Diazolösung    lässt man dann bei         5-10 CineineLösimgvon3,6Gewichtsteilen1-          (6'-Chlor-2'-methyl-4'-sulfophenyl)    -3-methyl-         5-pyr        azolon        83        %        ig        und    8     Gewichtsteilen        Ka-          liumacetat    in 100     Volumteilen    Wasser einflie  ssen.

   Nach beendeter Kupplung wird der     Vi-          nylsulfonfarbstoff    der folgenden Formel:  
EMI0001.0035     
      mit     Kaliumchlorid        ausgesalzen,    abgesaugt, mit  einer     Kaliumchloridlösung    gewaschen und ge  trocknet.  



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



  Das als     Diazokomponente    verwendete 1  Amino-4-methylbenzol-3-sulfonsäure -     (2'-meth-          oxy-5'-vinylsulfonyl)-phenylamid    kann wie       folgt    dargestellt werden:

         1-Nitro-4-methylbenzol-3-sulfonsäurechlorid     wird mit dem     Alkalisalz    des     Schwefelsäure-          esters    aus     1-Amino-2-methoxyphenyl-5-ss-oxy-          äthylsulfon    kondensiert, das Kondensations  produkt durch Behandeln mit einem Alkali    in die     Vinylsulfonverbindung    übergeführt und  die     Nitrogruppe    zur     Aminogruppe    reduziert.  Das Amin     sehmilzt    bei 162-163  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 compound is obtained from 1-amino-4-methylbenzene-3-sulfonic acid- (2'-methoxy-5'- vinylsulfonyl) phenyl amide with 1- (6'-chloro-2'-methyl-4'-sulfophenyl)

  -3-methyl-5-pyrazolone couples. Example: 3.8 parts by weight of 1-amino-4-methylbenzene-3-sulfonic acid (2'-methoxy-5'-vinylsulfonyl) phenylamide of the following formula:

    
EMI0001.0017
    are diazotized in the usual way in hydrochloric acid solution with 10 parts by volume of n-sodium nitrite solution. The diazo solution is then allowed to dissolve 3.6 parts by weight of 1- (6'-chloro-2'-methyl-4'-sulfophenyl) -3-methyl-5-pyrazolone 83% and 8 parts by weight of potassium acetate in 100 parts by volume at 5-10 ° C Pour in water.

   After the coupling is complete, the vinyl sulfone dye has the following formula:
EMI0001.0035
      salted out with potassium chloride, filtered off with suction, washed with a potassium chloride solution and dried ge.



  The product thus obtained is a yellow, water-soluble powder which dyes wool in yellow shades of good fastness properties.



  The 1-amino-4-methylbenzene-3-sulfonic acid - (2'-methoxy-5'-vinylsulfonyl) -phenylamide used as the diazo component can be represented as follows:

         1-Nitro-4-methylbenzene-3-sulfonic acid chloride is condensed with the alkali salt of the sulfuric acid ester from 1-amino-2-methoxyphenyl-5-ss-oxy ethyl sulfone, and the condensation product is converted into the vinyl sulfone compound by treatment with an alkali and the nitro group is reduced to the amino group. The amine melts at 162-163 C.

Claims (1)

PATENTANSPR.LTCH Verfahren zur Herstellung eines Vinylsul- Tonfarbstoffes, dadurch gekennzeichnet, da13 man die Diazoniumv erbindung aus 1-Amino- 4-methylbenzol - 3 - sulf onsäure - (2' - methoxy-5- vinyIsulfonyl)-phenylamid mit 1-(6'-Chlor-2'- methyl-4'-sulfopheny 1) -3 - methy 1- 5 - pyrazolon kuppelt. PATENTANSPR.LTCH Process for the production of a vinyl sulphon clay dye, characterized in that the diazonium compound is obtained from 1-amino-4-methylbenzene-3-sulfonic acid (2'-methoxy-5-vinyl isulfonyl) -phenylamide with 1- (6 '-Chlor-2'-methyl-4'-sulfopheny 1) -3 - methy 1- 5 - pyrazolone couples. Das so erhaltene Produkt stellt, ein gelbes, wasserlösliches Pulver dar, das Wolle in gel ben Tönen von guten Eehtheitseigensehaften färbt. The product obtained in this way is a yellow, water-soluble powder which dyes wool in yellow shades with good integrity properties.
CH302019D 1951-07-16 1951-07-16 Process for the preparation of a vinyl sulfone dye. CH302019A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH296001T 1951-07-16
CH302019T 1951-07-16

Publications (1)

Publication Number Publication Date
CH302019A true CH302019A (en) 1954-09-30

Family

ID=25733652

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302019D CH302019A (en) 1951-07-16 1951-07-16 Process for the preparation of a vinyl sulfone dye.

Country Status (1)

Country Link
CH (1) CH302019A (en)

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