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CH238463A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH238463A
CH238463A CH238463DA CH238463A CH 238463 A CH238463 A CH 238463A CH 238463D A CH238463D A CH 238463DA CH 238463 A CH238463 A CH 238463A
Authority
CH
Switzerland
Prior art keywords
parts
dye
azo dye
oxyethylsulfone
pyrazolone
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 CH238463A publication Critical patent/CH238463A/en

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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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • 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

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

Description

  

      Verfahren    zur     Herstellung    eines neuen     Azofarbstoffes.       Es wurde gefunden, dass man einen neuen       Azofarbstoff    erhält, wenn man 1     142o1        dia.zo-          tiertes        1-Aminobenzol-4-ss-oxyäthyl-sulfon,     1     Mol        1-(2'-Chlor)-phenyl-3-methyl-5-pyrazo-          lon    und 1     Mol        Bernsteinsäureanhydrid    derart  aufeinander einwirken lässt,

   dass die     Diazo-          verbindung    in     4-Stellung    des     Pyrazolonker-          nes    eingreift und dass die     Oxygruppe    des       Oxyäthylsulfonrestes    zu einem sauren Bern  steinsäureester verestert wird.  



  Der neue Farbstoff ist ein     gelboranges     Pulver, das sich in Wasser klar mit gelber  Farbe löst und     Acetatkunstseide    aus neutra  ler wässeriger Lösung unter Zusatz von Na  triumsulfat in reinen gelben Tönen von vor  züglichen Echtheitseigenschaften färbt.  



       Beispiel:     20,1 Teile     1-Aminobenzol-4-ss-oxyäthyl-          sulfon    werden     mit    25 Teilen 30%iger Salz  säure in 50 Teilen Wasser gelöst und bei 5  bis 10  mit 25 Teilen     4-n-Natriumnitritlösung          diazotiert.    Die klare, gelborange     Diazolösung     lässt man bei 5-10  zu einer Lösung von    21 Teilen     1-(2'-Chlor)-phenyl-3-methyl-5-pyr-          azolon,    15 Teilen 30%iger Natronlauge und  25 Teilen     Natriumcarbonat    in 200 Teilen  Wasser fliessen.

   Man     rührt    bis zur Beendi  gung der     Farbstoffbildung    bei 10-15 , saugt  dann den unlöslichen Farbstoff ab, wäscht  mit 200 Teilen Wasser und     trocknet    bei 50  bis 60 .  



  42 Teile des so erhaltenen Farbstoffes  werden bei 60-70  in 250 Teilen Eisessig ge  löst und in diese Lösung 12,5 Teile Bernstein  säureanhydrid eingetragen. Man erwärmt  während 2     Stunden    auf 100-110 , lässt er  kalten und giesst dann in 500 Teile Eiswasser,  filtriert den ausgefallenen Farbstoff ab und  wäscht mit 10%iger     Kochsalzlösung    nach.  Den Filterrückstand löst man mit der nötigen  Menge     Natriumcarbonat    in 400 Teilen Was  ser von     20-30 .    Aus der klaren Lösung     wird     das     Natriumsalz    des     Parbstoffes    durch Zu  gabe von 50 Teilen     Natriumchlorid    gefällt.

    Man saugt ab, wäscht mit 10 %     iger        Natrium-          chloridlösung    und trocknet im     Vakuum    bei  50-55 . Als     Lösungsmittel        für    die Vereste-           rung    können ausser Eisessig auch andere ge  eignete Lösungsmittel, wie     Toluol,    Benzol,       Xylol    usw., verwendet werden.



      Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 142o1 dia.zo- tosed 1-aminobenzene-4-ss-oxyethylsulfone, 1 mole of 1- (2'-chloro) -phenyl-3-methyl-5 pyrazolone and 1 mole of succinic anhydride to act on each other

   that the diazo compound intervenes in the 4-position of the pyrazolone nucleus and that the oxy group of the oxyethylsulfone residue is esterified to an acidic succinic acid ester.



  The new dye is a yellow-orange powder that dissolves in water with a clear yellow color and dyes acetate rayon from neutral aqueous solution with the addition of sodium sulfate in pure yellow shades with excellent fastness properties.



       Example: 20.1 parts of 1-aminobenzene-4-ss-oxyethyl sulfone are dissolved with 25 parts of 30% hydrochloric acid in 50 parts of water and diazotized at 5 to 10 with 25 parts of 4-n-sodium nitrite solution. The clear, yellow-orange diazo solution is added at 5-10 to a solution of 21 parts of 1- (2'-chloro) -phenyl-3-methyl-5-pyrazolone, 15 parts of 30% strength sodium hydroxide solution and 25 parts of sodium carbonate in 200 Share water flow.

   The mixture is stirred until the formation of the dye has ended at 10-15, then the insoluble dye is filtered off with suction, washed with 200 parts of water and dried at 50 to 60.



  42 parts of the dye thus obtained are dissolved in 250 parts of glacial acetic acid at 60-70 and 12.5 parts of succinic anhydride are introduced into this solution. The mixture is heated to 100-110 for 2 hours, allowed to cool and then poured into 500 parts of ice water, the precipitated dye is filtered off and washed with 10% sodium chloride solution. The filter residue is dissolved with the necessary amount of sodium carbonate in 400 parts of water from 20-30. The sodium salt of the paraffin is precipitated from the clear solution by adding 50 parts of sodium chloride.

    It is suctioned off, washed with 10% sodium chloride solution and dried in vacuo at 50-55. In addition to glacial acetic acid, other suitable solvents, such as toluene, benzene, xylene, etc., can also be used as solvents for the esterification.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man 1 Mol diazotiertes 1-Aminobenzol-4-ss- oxyäthylsulfon, 1 Mol 1-(2'-Chlor)-pheny 1-3- methyl-5-pyrazolon und 1 Mol Bernstein säureanhydrid derart aufeinander einwirken lässt, PATENT CLAIM: Process for the preparation of a new azo dye, characterized in that 1 mol of diazotized 1-aminobenzene-4-ss- oxyethylsulfone, 1 mol of 1- (2'-chloro) -pheny 1-3-methyl-5-pyrazolone and 1 Mols of succinic anhydride interact da.ss die Diazoverbindung in 4-Stellung des Pyrazolonkernes eingreift und dass die Oxygruppe des Oxyäthylsulfonrestes zu einem sauren Bernsteinsäureester verestert wird. Der neue Farbstoff ist ein gelboranges Pulver, das sich in Wasser klar mit gelber Farbe löst und Acetatkunstseide aus neutra ler wässeriger Lösung unter Zusatz von Na triumsulfat in reinen gelben Tönen von vor züglichen Echtheitseigenschaften färbt. da.ss the diazo compound intervenes in the 4-position of the pyrazolone nucleus and that the oxy group of the oxyethylsulfone residue is esterified to an acidic succinic acid ester. The new dye is a yellow-orange powder that dissolves in water with a clear yellow color and dyes acetate rayon from neutral aqueous solution with the addition of sodium sulfate in pure yellow shades with excellent fastness properties.
CH238463D 1943-09-02 1943-09-02 Process for the production of a new azo dye. CH238463A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH236764T 1943-09-02

Publications (1)

Publication Number Publication Date
CH238463A true CH238463A (en) 1945-07-15

Family

ID=4459600

Family Applications (8)

Application Number Title Priority Date Filing Date
CH238466D CH238466A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238463D CH238463A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238465D CH238465A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238464D CH238464A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238462D CH238462A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238460D CH238460A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH236764D CH236764A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238461D CH238461A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH238466D CH238466A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.

Family Applications After (6)

Application Number Title Priority Date Filing Date
CH238465D CH238465A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238464D CH238464A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238462D CH238462A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238460D CH238460A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH236764D CH236764A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.
CH238461D CH238461A (en) 1943-09-02 1943-09-02 Process for the production of a new azo dye.

Country Status (1)

Country Link
CH (8) CH238466A (en)

Also Published As

Publication number Publication date
CH238461A (en) 1945-07-15
CH238460A (en) 1945-07-15
CH238462A (en) 1945-07-15
CH236764A (en) 1945-03-15
CH238464A (en) 1945-07-15
CH238466A (en) 1945-07-15
CH238465A (en) 1945-07-15

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