DE286095C - - Google Patents

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- M 286095 CLASS 22 #. GROUP

FARBENFABRIKEN vorm. FRIEDR. BAYER & CO. in LEVERKUSEN b. CÖLN a. Rh.

Process for the preparation of anthraquinone acridones. Patented in the German Empire on March 3, 1914.

It became a surprising observation

■ made that the 'N-anthraquinonylization, which one z. B. by the action of oxalyl chloride on arylaminoanthraquinones or obtained by condensation of chloranthraquinones with isatins, under the influence of Condensing agents, such as aluminum chloride, sulfuric acid, alkalis, etc., are used as vat dyes skip technically important anthraquinone acridones.

Instead of the anthraquinonylisatins, the anthraquinonylisatin acids obtainable therefrom by hydrolysis can also be used or the salts thereof are subjected to condensation.

When carrying out the condensation in alkaline solution, taking as intermediates If anthraquinonylizatin acid salts are formed, one obtains a by adding hydrosulfite Vat, which can be used directly for dyeing.

Example 1.

10 parts of isatin obtained by exposure from oxalyl chloride to i-phenylaminoanthraquinone (orange colored crystals, whose Solution in organic solvents such as sulfuric acid is yellow, in alkali it is red) heated to boiling for a short time in 50 parts of nitrobenzene with 10 parts of aluminum chloride.

It is then allowed to cool to 70 ° and mixed with 20 parts of alcohol. When cooling down the reaction product separates out in the form of shiny metallic needles. It turns out to be identical to the anthraquinone acridone, which is composed of i-chloroanthraquinone and Anthranilic acid is formed (see patent specification 221853, class 22 b, example 1).

Example 2.

10 parts of isatin, obtained by condensation of i-chloroanthraquinone and isatin (identical to the isatin from i-phenylaminoanthraquinone and oxalyl chloride) are suspended in 200 parts of water and boiled with 10 parts of sodium hydroxide solution (33 percent) heated. The substance turns red with the formation of anthraquinonylisatin acid Salt (red crystals, the solution of which in concentrated sulfuric acid is yellow) in solution and with further boiling a condensation product separates in the form of violet ones Crystals from which are sucked off, washed and dried. The received The dye is identical to the product obtained in Example 1.

Example 3.

10 parts of the isatin obtained by the action of oxalyl chloride on i-p-tolylaminoanthraquinone (orange colored crystals, which are concentrated in organic solvents as well Sulfuric acid yellow, dissolve red in alkali), become sulfuric acid in 100 parts (66 ° Be) entered at 100 ° and heated for 2 hours at this temperature with stirring. It is then allowed to cool, then poured into cold water, boiled, filtered and washed acid free. After drying, the re-

Action product recrystallized from boiling nitrobenzene or quinoline. So you get metallic shiny crystals which are identical to that from i-p-tolylaminoanthraquinone-2-carboxylic acid (see patent specification 237236, class 22 b, example 2) obtained anthraquinone acridone.

In an analogous manner, the isatin is obtained from ι · 5-di-p-tolylaminoanthraquinone and oxalyl chloride (orange colored crystals, which in organic solvents as well as concentrated Sulfuric acid with yellow, go into solution in alkali with blue color) until now not described acridone, which is in nitrobenzene with violet and in concentrated Dissolves sulfuric acid with a red color. When treated with alkaline hydrosulphite it is preserved a blue-violet vat, which on cotton has excellent blue colorations Creates authenticity.

Example 4.

10 parts of the isatin obtained by condensation of i-p-Tolylaminoanthraquinone with oxalyl chloride, are in the form of a fine Paste in 500 parts of water with 10 parts of hydrosulfite and 75 parts of sodium hydroxide solution (30 ° Be) heated to 60 °. The substance goes into solution and forms a red-brown vat, which can be used directly for dyeing after dilution and cooling. From this dyeings are obtained on cotton, which correspond to those of the acridone described in Example 3. From the The acridone can be isolated from the vat by blowing it out.

Example 5.

5 parts of isatin, obtained by condensation of i-s-di-ß-naphthy'laminoanthraquinone and oxalyl chloride (brown crystals, which in organic solvents as well as concentrated Sulfuric acid with red-brown, in alkali with red color go into solution) registered in 30 parts of molten caustic potash at 180 °. After the strong foam development has stopped, you continue to heat to 220 ° until nothing has changed Starting material is more to be proven. It is then allowed to cool, the melt is dissolved in Water on and heated for complete separation of the dye formed 'under Introducing air to boil. The reaction product separates in the form of a bronze-shining crystal powder, which is filtered, washed and dried. That Acridon obtained in this way, as yet unknown, is extremely difficult to dissolve in boiling Quinoline is red in color and can be obtained from it in crystallized form in the form of fine needles which give a red solution in concentrated sulfuric acid. By alkaline Hydrosulfite solution, it can be brought into solution and thus provides a blue-violet vat, from which brown-violet dyeings are obtained on cotton.

Instead of the anthraquinonylisatins mentioned, their derivatives, which are substituted in the aromatic or in the anthraquinone nucleus, e.g. B. Anthraquinonylhalogenisatins, Anthraquinonylmethylisatins, anthraquinonylnaphthisatins, 1x4-methylaminoanthraquinonylisatins etc., for example, isatin provides i-m-chlorophenylanthraquinone and oxalyl chloride, an acridone which dissolves in concentrated sulfuric acid with a red-brown color and from which Vat produces vivid red colors on cotton. From the isatin from i-benzoylamino-4-p-tolylaminoanthraquinone and oxalyl chloride, an acridone is obtained, which dissolves brown in concentrated sulfuric acid and turns off the vat dyes cotton in excellent, genuine dark brown tones.

Claims (1)

Patent claim: _g Process for the preparation of anthraquinone acridones, characterized in that the N-anthraquinonylisatins or anthraquinonylisatin acids or their salts treated with condensing agents.