CH133385A - Process for the production of an anthraquinone derivative. - Google Patents

Process for the production of an anthraquinone derivative.

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Publication number
CH133385A
CH133385A CH133385DA CH133385A CH 133385 A CH133385 A CH 133385A CH 133385D A CH133385D A CH 133385DA CH 133385 A CH133385 A CH 133385A
Authority
CH
Switzerland
Prior art keywords
production
anthraquinone derivative
water
formic acid
parts
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 CH133385A publication Critical patent/CH133385A/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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
    • C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
    • C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
    • C07C225/34—Amino anthraquinones

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

Description

  

  <B>Zusatzpatent</B> zum Hauptpatent Nr. 131358.         Verfahren    zur Herstellung eines     Anthr        achinonderivates.       Es wurde gefunden, dass man ein     Anthra-          chinonderivat    erhält, wenn man     1,4-Diainino-          anthrachinon,        Benzaldehyd    und Ameisensäure  aufeinander einwirken lässt und das so er  haltone Produkt     sulfiert.    Der entstandene       Farbstoff    stellt wahrscheinlich eine     Disulfo-          säure    eines     Dibenzyl-1,4-diaminoanthrachinons     dar,

   welches selbst durch die Einwirkung  der Ameisensäure auf das Kondensations  produkt des     Aldehydes    mit dein     Amino-          anthrachinon    oder durch die Einwirkung des       Aldehydes    auf das Kondensationsprodukt der  Ameisensäure mit dem     Aminoanthrachinon     entstanden sein kann. Er bildet ein dunkel  blaues, in Wasser leicht mit     reinblauer    Farbe  lösliches Pulver und färbt urgebeizte Wolle  aus saurem Bad in blauen Tönen an.  



       Beispiel:     30 Teile     1,4-Diaminoanthrachinon    werden  im emaillierten Kessel unter gutem Rühren  in 150 Teilen 83,5     o/oiger    Ameisensäure sus  pendiert. Zu dieser Suspension werden bei    gewöhnlicher Temperatur 30 Teile Benz  aldehyd zugesetzt. Es wird alsdann bei       Wasserbadtemperatur    so lange gerührt, bis  eine in Nitrobenzol gelöste Probe keine wei  tere     Nuancenversohiebung    nach grün mehr  zeigt. Nach Erreichung dieses Zustandes wird  das Reaktionsprodukt mit Wasser verdünnt,  abgerutscht, gewaschen und getrocknet. Das  neue Produkt stellt ein dunkelgefärbtes Pulver  dar, welches in organischen Lösungsmitteln  mit     reinblauer    Farbe löslich ist.

   Die Lösung  in konzentrierter Schwefelsäure ist braun  gefärbt.  



  50 Teile des nach Angaben des obigen  Absatzes dargestellten Kondensationsproduk  tes werden in 200 Teilen Monohydrat gelöst  und langsam mit 200 Teilen 28     o/oigem        Oleum     versetzt. Die     Sulfierungsmasse    wird so lange  bei 40 bis 45 o gehalten, bis eine Probe in  Wasser vollständige Löslichkeit zeigt. Nach  Eingiessen in Eiswasser wird in üblicher  Weise     ausgesalzen,    abgesaugt und getrocknet.  Der     Farbstoff    stellt ein dunkelblaues Pulver      dar, das Wolle aus     saurem    Bad in     blauere     Tönen färbt.



  <B> Additional patent </B> to main patent no. 131358. Process for the production of an anthracinone derivative. It has been found that an anthraquinone derivative is obtained if 1,4-diaininoanthraquinone, benzaldehyde and formic acid are allowed to act on one another and the product thus obtained is sulfated. The resulting dye is probably a disulphonic acid of a dibenzyl-1,4-diaminoanthraquinone,

   which itself may have arisen through the action of formic acid on the condensation product of the aldehyde with the aminoanthraquinone or through the action of the aldehyde on the condensation product of formic acid with the aminoanthraquinone. It forms a dark blue powder that is easily soluble in water with a pure blue color and stains primed wool from an acid bath in blue tones.



       Example: 30 parts of 1,4-diaminoanthraquinone are suspended in 150 parts of 83.5% formic acid in an enamelled kettle with thorough stirring. To this suspension, 30 parts of benzaldehyde are added at ordinary temperature. It is then stirred at water bath temperature until a sample dissolved in nitrobenzene no longer shows any further shifts in shades to green. After this state has been reached, the reaction product is diluted with water, slipped off, washed and dried. The new product is a dark-colored powder that is soluble in organic solvents with a pure blue color.

   The solution in concentrated sulfuric acid is brown in color.



  50 parts of the condensation product presented according to the above paragraph are dissolved in 200 parts of monohydrate and slowly mixed with 200 parts of 28% strength oleum. The sulphonation mass is kept at 40 to 45 o until a sample shows complete solubility in water. After pouring into ice water, it is salted out in the usual way, filtered off with suction and dried. The dye is a dark blue powder that dyes wool from an acid bath in bluer tones.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Anthra- chinonderivates, dadurch gekennzeichnet, dass man 1,4-Diaminoanthrachinorr, Benzaldehyd und Ameisensäure aufeinander einwirken lässt und das so erhaltene Produkt sulfiert. Der entstandene Farbstoff bildet ein dunkelblaues, in Wasser leicht mit reinblauer Farbe lös liches Pulver und färbt ungebeizte Wolle aus saurem Bad in blauen Tönen an. PATENT CLAIM: Process for the production of an anthrachinone derivative, characterized in that 1,4-diaminoanthraquinone, benzaldehyde and formic acid are allowed to act on one another and the product thus obtained is sulfated. The resulting dye forms a dark blue powder that is easily soluble in water with a pure blue color and stains unstained wool from an acidic bath in blue tones.
CH133385D 1926-08-26 1926-08-26 Process for the production of an anthraquinone derivative. CH133385A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH133385T 1926-08-26
CH131358T 1927-12-07

Publications (1)

Publication Number Publication Date
CH133385A true CH133385A (en) 1929-05-31

Family

ID=25711601

Family Applications (1)

Application Number Title Priority Date Filing Date
CH133385D CH133385A (en) 1926-08-26 1926-08-26 Process for the production of an anthraquinone derivative.

Country Status (1)

Country Link
CH (1) CH133385A (en)

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