[go: up one dir, main page]

CH238465A - Process for the production of a new azo dye. - Google Patents

Process for the production of a new azo dye.

Info

Publication number
CH238465A
CH238465A CH238465DA CH238465A CH 238465 A CH238465 A CH 238465A CH 238465D A CH238465D A CH 238465DA CH 238465 A CH238465 A CH 238465A
Authority
CH
Switzerland
Prior art keywords
parts
dye
azo dye
pyrazolone
new
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 CH238465A publication Critical patent/CH238465A/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

Landscapes

  • 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-oxyäthylsulfamid,     1     Mol        1-(2'-Chlor)-phenyl-3-methyl-5-pyrazo-          lon    und ein     Sulfonierungsmittel    derart auf  einander einwirken lässt,

   dass die     Diazoverbin-          dung    in     4-.Stellung    des     Pyrazolonkernes    ein  greift und die     Oxygruppe    des     OxyäthyIsulf-          amidrestes    zu einem sauren Schwefelsäure  ester 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  triumsulfat in gelben Tönen von vorzüg  lichen Echtheitseigenschaften färbt.  



       Beispiel:     21,6 Teile     1-Aminobenzol-4-ss-oxyäthyl-          sulfamid    werden mit 25 Teilen 30%iger Salz  säure in 50 Teilen Wasser gelöst und bei 5  bis     '-0     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 .  



  20 Teile des so erhaltenen Farbstoffes  werden bei 0-5  in 100 Teile Schwefelsäure  von 60      B6    eingetragen. Nach kurzer Zeit ist  alles mit gelber Farbe in Lösung gegangen.  Man rührt 1     Stunde    bei Raumtemperatur,  giesst dann auf 250 Teile Eis, filtriert ab und  wäscht mit 10%iger Kochsalzlösung nach.  Den Filterrückstand löst man mit der nötigen  Menge     Natriumcarbonat    in 200 Teilen Was  ser von 20-30 . Aus der klaren Lösung wird  das     Natriumsalz    des Farbstoffes durch Zu  gabe von     30-40    Teilen     Natriumchlorid    ge  fällt.

   Man saugt ab, wäscht mit 15%iger Na  triumchloridlösung und trocknet im Vakuum  bei     50-55 .    An Stelle der     Schwefelsäure     kann auch eine     schwefelsäureanhydridhaltige         Schwefelsäure oder     Chlorsulfonsäure    verwen  det werden.



  Process for the production of a new azo dye. It has been found that a new azo dye is obtained if 1 mole of diazotized 1-aminobenzene-4-ss-oxyethylsulfamide and 1 mole of 1- (2'-chloro) -phenyl-3-methyl-5-pyrazolone are used and lets a sulfonating agent act on each other in such a way that

   that the diazo compound intervenes in the 4-position of the pyrazolone nucleus and the oxy group of the oxyethyl sulfamide residue is esterified to form 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 neutral aqueous solution with the addition of sodium sulfate in yellow shades with excellent fastness properties.



       Example: 21.6 parts of 1-aminobenzene-4-ss-oxyethyl sulfamide are dissolved with 25 parts of 30% hydrochloric acid in 50 parts of water and diazotized at 5 to '-0 with 25 parts of 4-n-sodium nitrite solution. The clear, yellow-orange diazo solution is left 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 flow in 200 parts of water. The mixture is stirred until the formation of the dye is at 10-15, then the insoluble dye is filtered off with suction, washed with 200 parts of water and dried at 50 to 60.



  20 parts of the dye thus obtained are introduced at 0-5 in 100 parts of sulfuric acid of 60 B6. After a short time everything has dissolved 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 from 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% sodium chloride solution and dried in vacuo at 50-55. Instead of sulfuric acid, sulfuric acid or chlorosulfonic acid containing sulfuric acid anhydride can also be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Azofarbstoffes, dadurch gekennzeichnet, da.ss man 1 Mol diazotiertes 1-Aniinobenzol-4-ss- oxyäthylsulfamid, 1 Mol 1-(?'-Chlor)-phenyl- 3-methyl-5-pyrazolon und ein Sulfonierungs- mittel derart aufeinander einwirken lä.sst, PATENT CLAIM: Process for the preparation of a new azo dye, characterized in that 1 mol of diazotized 1-aniinobenzene-4-ss- oxyethylsulfamide, 1 mol of 1 - (? '- chloro) -phenyl-3-methyl-5-pyrazolone and a sulfonating agent can act on each other in such a way that dass die Diazoverbindung in 4-Stellung des Pyr- azolonkernes eingreift und die Oxvgruppe des Oxyäthylsulfaiiiidrestes zu einem sauren Sehwefelsäureester 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 triumsulfat in gelben Tönen von vorzüg lichen Echtheitseigenschaften färbt. that the diazo compound intervenes in the 4-position of the pyrazolone nucleus and the oxy group of the Oxyäthylsulfaiiiidrestes is esterified to an acidic sulfate. The new dye is a brownish-yellow powder that dissolves in water with a clear yellow color and dyes acetate artificial silk from neutral aqueous solution with the addition of sodium sulfate in yellow shades with excellent fastness properties.
CH238465D 1943-09-02 1943-09-02 Process for the production of a new azo dye. CH238465A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
CH238465A true CH238465A (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 (2)

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.

Family Applications After (5)

Application Number Title Priority Date Filing Date
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
CH238463A (en) 1945-07-15
CH238466A (en) 1945-07-15

Similar Documents

Publication Publication Date Title
CH238465A (en) Process for the production of a new azo dye.
CH211819A (en) Process for the preparation of an azo dye.
CH211822A (en) Process for the preparation of an azo dye.
CH251799A (en) Process for the preparation of an azo dye.
CH220110A (en) Process for the production of a new azo dye.
CH209566A (en) Process for the preparation of an azo dye.
CH309791A (en) Process for the preparation of a yellow monoazo dye.
CH211803A (en) Process for the preparation of an azo dye.
CH211831A (en) Process for the preparation of an azo dye.
CH211825A (en) Process for the preparation of an azo dye.
CH211804A (en) Process for the preparation of an azo dye.
CH112532A (en) Process for the production of a new dye.
CH309793A (en) Process for the preparation of a yellow monoazo dye.
CH219413A (en) Process for the preparation of a new, water-soluble dye for dyeing and printing acetate silk.
CH211815A (en) Process for the preparation of an azo dye.
CH249780A (en) Process for the preparation of an azo dye.
CH229358A (en) Process for the preparation of a trisazo dye.
CH202248A (en) Process for the preparation of an azo dye.
CH207512A (en) Process for the preparation of an azo dye.
CH238336A (en) Process for the preparation of a new disazo dye.
CH211806A (en) Process for the preparation of an azo dye.
CH249784A (en) Process for the preparation of an azo dye.
CH178224A (en) Process for the production of a new dye.
CH200063A (en) Process for the preparation of an azo dye.
CH182399A (en) Process for the production of a new azo dye.