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CH238460A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH238460A
CH238460A CH238460DA CH238460A CH 238460 A CH238460 A CH 238460A CH 238460D A CH238460D A CH 238460DA CH 238460 A CH238460 A CH 238460A
Authority
CH
Switzerland
Prior art keywords
oxy
parts
production
dye
azo dye
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 CH238460A publication Critical patent/CH238460A/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
    • 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     Mol        diazo-          tiertes    1-     Aminobenzol    - 4     -ss-        oxyäthylsulfon,     1     Mol        1-Oxy-4-methylbenzol    und ein     Sulfo-          nierungsmittel    derart aufeinander einwirken       lässt,

      dass die     Diazoverbindung    in     2'-Stellung     des     1'-Oxy-4-methylbenzohs    eingreift und die       Oxygruppe    des     Oxyäthylsulfonrestes    zu  einem sauren     Schwefelsäureester        verestert     wird.  



  Der neue     Farbstoff    ist ein braungelbes  Pulver, das sich in     Wasser    klar mit gelber  Farbe löst und     Acetatkunstseide    aus neutra  ler wässeriger     Lösung    unter Zusatz von     Na-          triums@ulfat    in kräftigen     .gelben    Tönen von  vorzüglichen     Echtheitseigenschaften    färbt.

    <I>Beispiel:</I>  20,1 Teile     1-Amin.obenzol-4-ss-oxyäthyl-          sulfon    werden mit 25 Teilen     30%iger    Salz  säure in 50 Teilen Wasser gelöst und bei  5-10  mit<B>25</B> Teilen     4-n-Natriumnitritlösung          diazotiert.    Die klare, gelborange     Diazolösung     lässt man bei<B>5-10'</B> zu einer Lösung von    10,8 Teilen     1-Oxy-4-methylbenzol,    15 Teilen  30%iger Natronlauge und 25 Teilen     Na-          triumcarbonat    in 200 Teilen Wasser     fliessen.     Man rührt bis zur Beendigung der Farbstoff  bildung bei     10-159,

      saugt dann den unlös  lichen Farbstoff ab, wäscht mit 2100 Teilen  Wasser und trocknet bei 50-60 .  



  20 Teile des so     erhaltenen    Farbstoffes  werden bei 0-5  in 100 Teile Schwefelsäure  von<B>60'B6</B>     eingetragen.    Nach kurzer Zeit  ist alles mit gelber Farbe in Lösung gegan  gen. Man rührt 1 Stunde bei Raumtempera  tur, giesst dann auf 2'50 Teile Eis, filtriert  ab und wäscht mit 10%iger     Kochsalzlösung     nach.

   Den Filterrückstand löst man mit der       nötigen    Menge     Natriumcarbonat    in 200 Tei  len Wasser von     20=30 .    Aus der klaren Lö  sung wird das     Natriumsalz    des Farbstoffes  durch Zugabe von     30--40    Teilen     Natrium-          ehlorid    gefällt. Man saugt ab, wäscht mit  15 %     iger        Natriumch'loridlösung    und trocknet  im Vakuum bei 50=55  . An Stelle der  Schwefelsäure kann auch eine     echwefelsäure-          anhydridhaltige    Schwefelsäure oder auch       Chlorsulfonsäure    verwendet werden.



  Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mol of diazotized 1-aminobenzene-4-s-oxyethylsulfone, 1 mol of 1-oxy-4-methylbenzene and a sulfonating agent are allowed to act on one another in such a way that

      that the diazo compound intervenes in the 2'-position of the 1'-oxy-4-methylbenzoh and the oxy group of the Oxyäthylsulfonrestes is esterified to an acidic sulfuric acid ester.



  The new dye is a brownish-yellow powder that dissolves in water with a clear yellow color and dyes acetate artificial silk from a neutral aqueous solution with the addition of sodium sulphate in strong yellow tones with excellent fastness properties.

    <I> Example: </I> 20.1 parts of 1-amin.obenzene-4-ss-oxyethyl sulfone are dissolved with 25 parts of 30% hydrochloric acid in 50 parts of water and at 5-10 with <B> 25 </B> Divide diazotized 4N sodium nitrite solution. The clear, yellow-orange diazo solution is allowed to add at 5-10 parts to a solution of 10.8 parts of 1-oxy-4-methylbenzene, 15 parts of 30% strength sodium hydroxide solution and 25 parts of sodium carbonate in 200 parts Water flow. The mixture is stirred until the formation of the dye at 10-159,

      Then sucks off the insoluble dye, washed with 2100 parts of water and dried at 50-60.



  20 parts of the dye thus obtained are introduced at 0-5 in 100 parts of sulfuric acid of <B> 60'B6 </B>. After a short time everything has gone into solution with a yellow color. The mixture is stirred for 1 hour at room temperature, then poured onto 250 parts of ice, filtered off and washed with 10% sodium chloride solution.

   The filter residue is dissolved with the necessary amount of sodium carbonate in 200 parts of water of 20 = 30. The sodium salt of the dye is precipitated from the clear solution by adding 30-40 parts of sodium chloride. It is suctioned off, washed with 15% strength sodium chloride solution and dried in vacuo at 50 = 55. Instead of sulfuric acid, sulfuric acid containing anhydride or chlorosulfonic acid can also be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, dass man 1 Mdl diazotiertes 1-Aminobenzol-4-ss- oxyäthylsulfon, 1 Mol 1-Oxy-4-methylbenzol und ein Sulfonierungsmittel derart aufein ander einwirken lässt, PATENT CLAIM: Process for the production of a new azo dye, characterized in that 1 mol of diazotized 1-aminobenzene-4-ss-oxyethylsulfone, 1 mol of 1-oxy-4-methylbenzene and a sulfonating agent are allowed to act on one another, dass die Dia.zoverbin- dung in 2-Stellung des 1-Oxy-4-methy lben- zols eingreift und die Oxybruppe des Oxy- äthylsulfonrestes zu einem sauren Schwefel säureester verestert wird. that the dia.zo compound intervenes in the 2-position of the 1-oxy-4-methylbenzene and the oxy group of the oxyethylsulfone residue is esterified to an acidic sulfuric acid ester. Der neue Farbstoff ist ein braungelbes Pulver, das sich in Wasser klar mit gelber Farbe löst und Nceta,t,knnstseide aus neutra ler wässeriger Lösung unter Zusatz von Na- triumsulfa.t in kräftigen gelben Tönen von vorzüglichen Echtheitseigenschaften färbt. The new dye is a brownish-yellow powder that dissolves in water clearly with a yellow color and dyes Nceta, t, artificial silk from a neutral aqueous solution with the addition of sodium sulfa, t in strong yellow shades with excellent fastness properties.
CH238460D 1943-09-02 1943-09-02 Process for the production of a new azo dye. CH238460A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH238460A true CH238460A (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 (5)

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.

Family Applications After (2)

Application Number Title Priority Date Filing Date
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
CH238462A (en) 1945-07-15
CH236764A (en) 1945-03-15
CH238464A (en) 1945-07-15
CH238463A (en) 1945-07-15
CH238466A (en) 1945-07-15
CH238465A (en) 1945-07-15

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