CH192976A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH192976A
CH192976A CH192976DA CH192976A CH 192976 A CH192976 A CH 192976A CH 192976D A CH192976D A CH 192976DA CH 192976 A CH192976 A CH 192976A
Authority
CH
Switzerland
Prior art keywords
azo dye
parts
dye
diazotized
ogynaphthalene
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH192976A publication Critical patent/CH192976A/en

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Classifications

    • 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
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02Disazo dyes
    • C09B31/08Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
    • 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
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/30Other polyazo dyes
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

  

      Zusatzpatent    zum     Hauptpatent    Nr. 187120.    Verfahren zur Herstellung eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    erhält,     wenn.    man 1     Mol    4',4"  Diaminodibenzoyl -1,     3;

      -     diamino    - 8 -     ogynaph        -          thalin-6-sulfonsäure    mit 1     Mol,des        ,diazotier-          ten        Azofarbstoffes    aus einem     diazotierten        0-          Ester    der     1-Amino-$-ogynaphthalin-3"6-@di-          sulfonsäure    und     a-Naphthylamin        vereinigt,     und indem     erhaltenen    Kupplungsprodukt die       Estergruppe    ,

  durch     Behandeln    mit     Versei-          fungsmitteln    spaltet. Der so erhaltene Farb  stoff bildet ein dunkles Pulver, das sich in  Wasser mit blauer Farbe löst und Baumwolle  in blauen Tönen färbt, ,die durch Weiter  diazotieren auf -der Faser und Entwickeln       mit        1-Phenyl-3-methyl-@5-pyrazolon    grün,  licht und waschecht     werden.     



  <I>Beispiel:</I>  23,7 Teile der     1-Amino-8-toluolsulfogy-          naphthalin-3.        6-disulfonsäure    werden in 600  Teilen Wasser gelöst und auf 0   abgekühlt.  Hierauf     gibt    man 121 Teile einer 30%igen  Salzsäure zu und lässt unter gutem Rühren    17,5     Teile    einer     2;0    %     igen        Natriumnitritlösung     unter die     Flüssigkeitsoberfläche    einlaufen.  Nach beendigter     Diazotierung    .gibt man 7,2  Teile     a-Naphthylamin    als Chlorhydrat ge  löst zu.

   Die     Kupplung    geht ohne     weitere    Zu  sätze sehr gut und man lässt über Nacht  rühren. Durch Zusatz von 8 Teilen Natrium  karbonat und 40 Teilen einer 4%igen     Na-          triumhydrogydlösung    wird der gebildete       Monoazofarbstoff    in Lösung gebracht, 17,5       Teile    einer 2,0 %     igen        Natriumnitritlösung     eingetragen und bei 0 bis 5   indirekt     diazo-          tiert,

      indem man 30 Teile einer 30 %     igen     Salzsäure     unter    gutem Rühren auf einmal       einstürzt.    Dann lässt man noch 2     Stunden     bei 10 bis 15   rühren, filtriert die ausge  schiedene     Diazoverbindung    ab und schwemmt  sie in 1000 Teilen Eiswasser an.

   Diese     Di-          azoverbindung    des     Monoazofarbstoffes    lässt  man in eine kalte Lösung aus 24,6 Teilen  4',4" -     Diaminodibenzoyl-1,    3 -     diamino    -,8     -ogy-          naphthalin-6-sulfonsäure    und 15 Teilen Na  triumkarbonat in 500 Teilen Wasser ein-      laufen und einige     Stunden    rühren. Nach be  endeter     Kupplung    wird der     Disazofarbstoff          ausgesalzen,        abfiltriert    und in 500 Teilen  einer 2%igen     Natriumhydrogydlösung    an  gerührt.

   Zur     Verseifung    des     Toluolsulfo-          esters    erwärmt man etwa 1/4 Stunde auf     ,6!0     bis     7O',    neutralisiert mit Essigsäure     und        fil-          triert    den ausgefallenen verseiften     Disazo-          farbstoff    ab.



      Additional patent to main patent No. 187120. Process for the production of a new azo dye. It has been found that a new azo dye is obtained when. one mole of 4 ', 4 "diaminodibenzoyl -1, 3;

      - diamino - 8 - ogynaph - thalin-6-sulfonic acid combined with 1 mol of the, diazotized azo dye from a diazotized 0-ester of 1-amino- $ - ogynaphthalene-3 "6- @ disulfonic acid and a-naphthylamine , and in the coupling product obtained the ester group,

  splits by treatment with saponifying agents. The dye thus obtained forms a dark powder that dissolves in water with a blue color and dyes cotton in blue tones, which by further diazotizing on the fiber and developing with 1-phenyl-3-methyl- @ 5-pyrazolone green , light and washfast.



  <I> Example: </I> 23.7 parts of 1-amino-8-toluenesulfogynaphthalene-3. 6-disulfonic acid are dissolved in 600 parts of water and cooled to zero. 121 parts of a 30% strength hydrochloric acid are then added and 17.5 parts of a 20% strength sodium nitrite solution are allowed to run under the surface of the liquid with thorough stirring. When the diazotization is complete, 7.2 parts of a-naphthylamine are dissolved in the form of a hydrochloride.

   The coupling works very well without further additives and the mixture is left to stir overnight. By adding 8 parts of sodium carbonate and 40 parts of a 4% sodium hydrogen solution, the monoazo dye formed is dissolved, 17.5 parts of a 2.0% sodium nitrite solution are added and diazotized indirectly at 0 to 5,

      by collapsing 30 parts of 30% hydrochloric acid at once with thorough stirring. The mixture is then left to stir for a further 2 hours at 10 to 15, the diazo compound which has separated out is filtered off and washed up in 1000 parts of ice water.

   This di-azo compound of the monoazo dye is left in a cold solution of 24.6 parts of 4 ', 4 "- diaminodibenzoyl-1, 3 - diamino -, 8 -ogynaphthalene-6-sulfonic acid and 15 parts of sodium carbonate in 500 parts of water run in and stir for a few hours After the coupling has ended, the disazo dye is salted out, filtered off and stirred in 500 parts of a 2% strength sodium hydrogen solution.

   To saponify the toluenesulphoester, it is heated for about 1/4 hour to 6.10 to 70 ', neutralized with acetic acid and the precipitated saponified disazo dye is filtered off.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man 1 Mol 4',4"-Diaminodibenzoyl-1,3-di- amino-8-ogynaphthalin-6-sulfonsäure mit 1 Mol des diazotierten Azofarbstoffes aus einem diazotierten 0-Ester der 1-Amino-8- ogynaphthalin-3,6-disulfonsäure und a-Naph- thylamin vereinigt, PATENT CLAIM: Process for the preparation of a new azo dye, characterized in that 1 mol of 4 ', 4 "-diaminodibenzoyl-1,3-di-amino-8-ogynaphthalene-6-sulfonic acid is mixed with 1 mol of the diazotized azo dye from a diazotized 0- Esters of 1-amino-8-ogynaphthalene-3,6-disulfonic acid and a-naphthylamine combined, und in dem erhaltenen Kupplungsprodukt die Estergruppe durch Behandeln mit Verseifungsmitteln spaltet. Der so erhaltene Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit blauer Farbe löst und Baumwolle in blauen Tönen färbt, die durch Weiterdiazotieren auf der Faser und Entwickeln mit 1-Phenyl-3-methyl-5- pyrazolon grün, licht- und waschecht werden. and in the coupling product obtained cleaves the ester group by treatment with saponifying agents. The dye thus obtained forms a dark powder which dissolves in water with a blue color and dyes cotton in blue tones, which by further diazotizing on the fiber and developing with 1-phenyl-3-methyl-5-pyrazolone are green, lightfast and washable will.
CH192976D 1934-09-29 1934-09-29 Process for the production of a new azo dye. CH192976A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH192976T 1934-09-29
CH187120T 1934-09-29

Publications (1)

Publication Number Publication Date
CH192976A true CH192976A (en) 1937-09-15

Family

ID=25721478

Family Applications (1)

Application Number Title Priority Date Filing Date
CH192976D CH192976A (en) 1934-09-29 1934-09-29 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (1) CH192976A (en)

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