CH291428A

CH291428A - Process for the preparation of a dye of the anthrapyridone series.

Info

Publication number: CH291428A
Authority: CH
Inventors: Ag Sandoz
Original assignee: Ag Sandoz
Priority date: 1950-06-30
Filing date: 1950-06-30
Publication date: 1953-06-15

Description

  

  Verfahren     zur        Herstellung    eines     Farbstoffes    der     Anthrapyridonreihe.            Clegenstand    des vorliegenden Patentes ist  ein Verfahren zur     Herstellung    eines Farbstof  fes der     Anthrapyridonreihe,    welches dadurch  gekennzeichnet ist,

   dass man     1-Amino-2-p-tert.          oety        lplienoxy-4-anilidoanthraehinon    mit einem       Benzoylessigsäurealkylester    umsetzt und das       erhaltene        C-Benzoylanthrapyridon    durch Be  handeln mit einem sulfonierenden Mittel in  die entsprechende     Disulfonsä.ure    überführt.

         Beispiel:          ?2,5    Teile     1-Aniino-2-p-tert.        octylphenoyy-          -1- < iililidoant.hrachinon    werden mit. 21 Teilen       Beilzoylessigsäureäthylester,    15 Teilen Nitro  benzol und 1,5 Teilen     Natriumcarbonat    auf  <B>1700</B> erhitzt und während 5 Stunden bei dieser  Temperatur unter     Abdestillieren    der<B>flüch-</B>  tigen     Reaktionsprodukte,    vorzugsweise mittels       ("begleiten    eines mässigen Stickstoffstromes  über die     Reaktionsmasse,    gerührt.

   Man kühlt       auf        l(_10     ab, verdünnt mit     -10    Teilen     Isopro-          pylalkoliol    und trennt die Base ab. Man er  hält rote Nadeln von     C-Benzoyl-2-p-tert.          oetylphenoxy-l-anilidoanthrapyridon,    die sich  in konzentrierter Schwefelsäure mit rein roter  Farbe lösen.  



  Bei einer Temperatur unterhalb 20  trägt       iuan    10 Teile der     Farbstoffbase    in eine     Mi-          schung    von 55 Teilen     Schwefelsäuremonohydrat          nn        d    1 3 'feilen     28o/oigeni        Oleum    ein. Nach       :3        Stunden    soll eine Probe in Wasser ohne       Rückstand    löslich sein; ist. dies nicht der Fall,  so muss noch etwas     Oleum    zugesetzt werden.

    Die     Sulfonieitzngsmasse    wird in eine Lösung    von 25 Teilen Kochsalz in 500 Teilen Wasser  gegossen, worauf der abgeschiedene Farbstoff  abgesaugt, gewaschen     and    getrocknet wird.  Er ist ein rotviolettes Pulver, das tierische  und synthetische     Polyamidfasern    in roten  Tönen von ausgezeichneter Walk- und Licht  echtheit färbt.



  Process for the preparation of a dye of the anthrapyridone series. The status of the present patent is a process for the preparation of a dye of the anthrapyridone series, which is characterized by

   that one 1-amino-2-p-tert. Oetylplienoxy-4-anilidoanthraehinone is reacted with an alkyl benzoylacetate and the C-benzoylanthrapyridone obtained is converted into the corresponding disulfonic acid by treatment with a sulfonating agent.

         Example:? 2.5 parts 1-aniino-2-p-tert. octylphenoyy- -1- <iililidoant.hrachinon are with. 21 parts of ethyl acetate, 15 parts of nitrobenzene and 1.5 parts of sodium carbonate are heated to 1700 and at this temperature for 5 hours while distilling off the volatile reaction products, preferably by means of (" accompanied by a moderate stream of nitrogen over the reaction mass, stirred.

   The mixture is cooled to 1/10, diluted with -10 parts of isopropyl alcohol, and the base is separated off. Red needles of C-benzoyl-2-p-tert-oetylphenoxy-1-anilidoanthrapyridone are obtained, which are dissolved in concentrated sulfuric acid solve pure red color.



  At a temperature below 20, 10 parts of the dyestuff base are incorporated into a mixture of 55 parts of sulfuric acid monohydrate and 13 'file 28% of oleum. After: 3 hours a sample should be soluble in water without residue; is. if this is not the case, some oleum must be added.

    The sulfonylation mass is poured into a solution of 25 parts of sodium chloride in 500 parts of water, whereupon the deposited dye is filtered off with suction, washed and dried. It is a red-violet powder that dyes animal and synthetic polyamide fibers in red shades with excellent fullness and lightfastness.

Claims

PATENT CLAIM: Process for the production of a dye of the anthrapyridone series, characterized in that 1-amino-2-p-tert. octylphenoxy-4-anilidoanthraquinone is reacted with an alkyl benzoylacetate and the C-benzoylanthrapyridone obtained is converted into the corresponding disulfonic acid by treatment with a sulfonating agent.

The new dye is a red-violet powder that dyes animal and synthetic polyamide fibers in red shades with excellent mill and lightfastness. SUBClaims: 1. Process according to claim, characterized in that the reaction with the alkyl benzoyl acetate is carried out in the presence of an organic solvent. 2. The method according to claim, characterized in that the implementation is carried out with the alkyl benzoyl acetate at elevated temperature. 3.

Process according to patent claim, characterized in that the reaction with the alkyl benzoyl acetate is carried out in the presence of a small amount of a weakly alkaline condensing agent. 4. The method according to claim, characterized in that the volatile reaction products are continuously removed during the reaction with the alkyl benzoyl acetic acid ester by passing a weak stream of an inert gas over the reaction mass. 5.

Process according to patent claim, characterized in that the benzoyl acetic acid ethyl ester is chosen as the benzoyl acetic acid alkyl ester.