[go: up one dir, main page]

CH252949A - Process for the preparation of a metallizable monoazo dye of the pyrazolone series. - Google Patents

Process for the preparation of a metallizable monoazo dye of the pyrazolone series.

Info

Publication number
CH252949A
CH252949A CH252949DA CH252949A CH 252949 A CH252949 A CH 252949A CH 252949D A CH252949D A CH 252949DA CH 252949 A CH252949 A CH 252949A
Authority
CH
Switzerland
Prior art keywords
pyrazolone
mol
methyl
monoazo dye
diazo
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R 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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH252949A publication Critical patent/CH252949A/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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/18—Monoazo compounds containing copper

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung eines     metallisierbaren        Monoazofarbatoffes    der     Pyrazolonreihe.            Gegenstand    vorliegenden     Patentes    ist ein  Verfahren zur Herstellung eines     metallisier-          baren        Monoazofarbstoffes    der     Pyrazolanreihe.     Das Verfahren ist dadurch gekennzeichnet,       da.ss    man 1     Mol    1-     Diazo    - 6 -     nitro    - 2 - ogy-         naphthalin    - 4 -     sulfansäure,

      2     Mol    1- (4'     -          Amino    -     phenyl)    - 3 -     methyl    - 5     -pyrazolon    und  1     Mol        Phosgen    derart aufeinander einwirken  lässt,     da.ss    ein     Monoazofarbstoff    der Formel  
EMI0001.0026     
    entsteht..

    Der neue     Mo.noazofarbstoff    stellt ein  dunkles Pulver dar, das sich in Wasser mit  roter und in konzentrierter Schwefelsäure  mit oranger Farbe löst und     Gellulosefasern     in braunorangen Tönen anfärbt, welche durch       Nachkupferung    in ein Rot von verbesserter  Nass- und Lichtechtheit übergehen.  



       Beispiel:     29,5 Teile     1-Diazo-6-nitro-2-ogy-naph-          t        halin    - 4 -     sulfonsäure    werden mit 40,4 Teilen  Harnstoff des 1 - (4' -     Aminophenyl)    - 3 -     me-          thyl    -     ä    -     py        razolons    in Gegenwart von über  schüssiger Soda zum     Monoazofarbstoff    ver  einigt. Nach mehrstündigem Rühren bei Eis  kühlung ist die     Diazoverbindung    verschwun  den. Man isoliert den Farbstoff mit Kochsalz.  Der getrocknete Farbstoff stellt ein dunkles  Pulver dar.

    



  Der Harnstoff des     1-(4'-Amino-phenyl)-          3-methyl-5-pyrazolons    lässt ,sich nach bekann-         ter    Methode darstellen, indem man 37,8 Teile       1-(4'-Amino-phenyl)-3-methyl-5-pyrazolon    in       sodaalkalischer    Lösung mit     Phosgen    konden  siert, bis keine freien     Aminogruppen    mehr  nachweisbar sind.  



  Zum gleichen Farbstoff gelangt man auch,  wenn man 29,5 Teile     1-Diazo-6-nitro-2-ogy-          naphthalin-4-sulfonsäure    mit 18,9 Teilen     1-(4'-          Amino-phenyl)-3-methyl-5-pyrazolon    in     soda-          alkalischer    Lösung kuppelt und den erhalte  nen     Aminomonoazofarbstoff    mit 18,9 Teilen       1-(4'-Amino-phenyl)-3-methyl-5-pyrazolon    in       sodaalkalischer        Lösung    mit     Phosgen    konden  siert, bis keine freien     Aminogruppen    mehr  nachweisbar sind.



  Process for the production of a metallizable monoazo carbate of the pyrazolone series. The present patent relates to a process for the production of a metallizable monoazo dye of the pyrazolane series. The process is characterized in that 1 mol of 1-diazo-6-nitro-2-ogynaphthalene-4-sulfanic acid,

      2 moles of 1- (4'-amino-phenyl) -3-methyl-5-pyrazolone and 1 mole of phosgene can act on one another in such a way that a monoazo dye of the formula
EMI0001.0026
    arises ..

    The new Mo.noazo dye is a dark powder that dissolves in water with red and in concentrated sulfuric acid with an orange color and dyes cellulose fibers in brown-orange tones, which change to a red with improved wet and light fastness through subsequent copper plating.



       Example: 29.5 parts of 1-diazo-6-nitro-2-ogy-naphthaline - 4 - sulfonic acid are mixed with 40.4 parts of urea of 1 - (4 '- aminophenyl) - 3 - methyl - Ä - Py razolons united in the presence of excess soda to form the monoazo dye. After stirring for several hours while cooling with ice, the diazo compound has disappeared. The dye is isolated with common salt. The dried dye is a dark powder.

    



  The urea of 1- (4'-aminophenyl) -3-methyl-5-pyrazolone can be prepared by a known method by adding 37.8 parts of 1- (4'-aminophenyl) -3- methyl-5-pyrazolone condenses in a soda-alkaline solution with phosgene until no more free amino groups can be detected.



  The same dye can also be obtained if 29.5 parts of 1-diazo-6-nitro-2-ogynaphthalene-4-sulfonic acid are mixed with 18.9 parts of 1- (4'-aminophenyl) -3-methyl- Coupling 5-pyrazolone in an alkaline soda solution and condenses the aminomonoazo dye obtained with 18.9 parts of 1- (4'-aminophenyl) -3-methyl-5-pyrazolone in an alkaline soda solution with phosgene until no more free amino groups are detectable.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines metalli- sierbaren Monoazofarbstoffes der Pyrazolon- reihe, dadurch gekennzeichnet, dass man 1 Mol 1-Diazo-6-nitro-2-ogy-naphthalin- 4 - sul- fonsäure, 2 Mol 1-(4'-A.mino-ph-enyl)-3-me- thyl-5-pyrazolon und 1 Mol Phosgen derart aufeinander einwirken lässt, PATENT CLAIM: Process for the preparation of a metallizable monoazo dye of the pyrazolone series, characterized in that 1 mol of 1-diazo-6-nitro-2-ogy-naphthalene-4-sulphonic acid, 2 mol of 1- (4'- A.mino-ph-enyl) -3-methyl-5-pyrazolone and 1 mole of phosgene can act on one another in such a way that dass ein Monoazo- farbstoff der Formel EMI0002.0010 entsteht. - Der- neue _Monoazofarbstoff - stellt . ein dunkles Pulver dar, das sich in Wasser mit roter- und in konzentrierter Schwefelsäure mit oränger Farbe löst und Cellulosefasern in braunorangen Tönen anfärbt, welche durch Nachkupferung in ein Rot von verbesserter Nass- und Lichtechtheit übergehen. UNTERANSPRüCHE: 1. that a monoazo dye of the formula EMI0002.0010 arises. - The new _monoazo dye - represents. a dark powder, which dissolves in water with red and in concentrated sulfuric acid with an orange color and dyes cellulose fibers in brown-orange tones, which change into a red with improved wet and light fastness due to copper plating. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 1 -Hol des Harnstoffes des 1-(4'-Amino-phenyl)-3-me- thyl-5-pyrazolans mit 1 Mol 1-Diazo-6-nitro- @;.-oxynaphthalin-4-sulfonsäure vereinigt. A method according to claim, characterized in that 1 -hol of the urea of 1- (4'-aminophenyl) -3-methyl-5-pyrazolane is mixed with 1 mol of 1-diazo-6-nitro- @ ;. -oxynaphthalene-4-sulfonic acid combined. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 1 Mol des Monoazofarbstoffes aus 1-Diazo-6-nitro-2-ozy- naphthalin-4-sulfonsäure und 1-(4'-Amino- phenyl) - 3 - methyl - 5 - pyrazölon mit- 1 Mol 1- (4' - Amiuo-phenyl) 2. The method according to claim, characterized in that 1 mol of the monoazo dye from 1-diazo-6-nitro-2-ozy- naphthalene-4-sulfonic acid and 1- (4'-aminophenyl) - 3 - methyl - 5 - pyrazolone with - 1 mol 1- (4 '- amiuo-phenyl) -8-methyl - 5 - pyrazolon mit Phosgen bis zum Verschwinden der pri mären Äminogruppen kondensiert. -8-methyl - 5 - pyrazolone condensed with phosgene until the primary amino groups disappear.
CH252949D 1945-12-27 1945-12-27 Process for the preparation of a metallizable monoazo dye of the pyrazolone series. CH252949A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252949T 1945-12-27
CH247443T 1945-12-27

Publications (1)

Publication Number Publication Date
CH252949A true CH252949A (en) 1948-01-31

Family

ID=25729208

Family Applications (1)

Application Number Title Priority Date Filing Date
CH252949D CH252949A (en) 1945-12-27 1945-12-27 Process for the preparation of a metallizable monoazo dye of the pyrazolone series.

Country Status (1)

Country Link
CH (1) CH252949A (en)

Similar Documents

Publication Publication Date Title
CH238453A (en) Process for the preparation of a copper-compatible polyazo dye.
CH252949A (en) Process for the preparation of a metallizable monoazo dye of the pyrazolone series.
CH252951A (en) Process for the preparation of a metallizable monoazo dye of the pyrazolone series.
CH222693A (en) Process for the preparation of a monoazo dye.
CH253881A (en) Process for the preparation of an azo dye of the pyrazolone series.
CH233185A (en) Process for the production of a new azo dye.
CH242998A (en) Process for the preparation of a copper-compatible polyazo dye.
CH265416A (en) Process for the preparation of a stilbene dye.
CH202747A (en) Process for the preparation of an azo dye.
CH265418A (en) Process for the preparation of a stilbene dye.
CH202743A (en) Process for the preparation of an azo dye.
CH242999A (en) Process for the preparation of a copper-compatible polyazo dye.
CH259329A (en) Process for the preparation of an azo dye.
CH180293A (en) Process for the production of a new dye.
CH202750A (en) Process for the preparation of an azo dye.
CH202746A (en) Process for the preparation of an azo dye.
CH252950A (en) Process for the preparation of a metallizable monoazo dye of the pyrazolone series.
CH180294A (en) Process for the production of a new dye.
CH257030A (en) Process for the production of a metallizable azo dye.
CH257288A (en) Process for the preparation of a new monoazo dye.
CH202749A (en) Process for the preparation of an azo dye.
CH265415A (en) Process for the preparation of a stilbene dye.
CH117275A (en) Process for the production of a new dye.
CH240364A (en) Process for the preparation of a disazo dye.
CH116729A (en) Process for the production of a new dye.