DE450921C - Process for the preparation of Kuepen dyes of the anthraquinone series - Google Patents

Description

Process for the preparation of vat dyes of the anthraquinone series. In the patent 237 236 (see also additional patents 237 237 and 248 i7o) the production of vat dyes of the anthraquinone series from i-nitro or i-chloroanthraquinone-2-carboxylic acids described. These acids are first converted into the aryl-i-aminoanthraquinone-2-carboxylic acids by heating with arylamines convicted; in a further operation the condensation takes place to one Acridone in such a way that those arylidoanthraquinone carboxylic acids are either directly or after the intermediate representation of derivatives, such as. B. the corresponding Acid halides treated with condensing agents.

It has now been found that it is possible to condense i-chloroanthraquinone-2-carboxylic acids with arylamines to aryl-i-amino - anthraquinone-2-carboxylic acids and the conversion to make these acids into the acridones in one operation and so the technically important acridones of the antraquinone series in a far more advantageous manner. It is sufficient here simply to heat the starting materials in solvents Absence of condensation agents or catalytically active substances, yes is their use sometimes for the rapid course of the reaction and the yield advantageous. The yields obtained in this process are very good. example i.

300 parts of nitrobenzene, 28.6 parts of i-chloroanthraquinone-a-carboxylic acid and 17.2 parts of ß-naphthylamine are heated to boiling under reflux until the Formation of the dye is complete. After cooling, the excreted ones are sucked up Crystals and freed them from the solvent in the usual way. The thus obtained The product is identical to that described in Patent Specification 237,236, Example 4 Dye.

Example 2.

300 parts of naphthalene, 28.6 parts of i-chloroanthraquinone-2-carboxylic acid, 15 parts of oxalic acid and 17.2 parts of β-naphthylamine are treated as in Example i. The cooled melt is freed from naphthalene by treatment with an organic solvent, whereby the dye is obtained in shiny red flakes.

Example 3.

300 parts of trichlorobenzene, 28.6 parts of i-chloroanthraquinone-2-carboxylic acid, 15.3 parts of p-chloroaniline and 12.4 parts of boric acid are brought to the boil on the reflux condenser heated until no more unchanged i-chloroanthraquinone-2-carboxylic acid available is. The work-up is carried out as indicated in the example. The product as well the yields are the same as in Example 3 of patent 237236.

Example q ..

300 parts of tricblobenzene, 28.6 parts of 1-chloroanthraquinone-2-carboxylic acid, 8.2 parts of anhydrous sodium acetate and 17.2 parts of β-naphthylamine. will be so long heated to boiling until no more acetic acid escapes, then 12.4 parts are added Boric acid is added and it boils until the dye formation has ended. It will suctioned off after cooling, the dye, as in Example 1, in crystallized Condition remains.

Example 5.

300 parts of trichlorobenzene, 28.6 parts of 1-chloroanthraquinone-2-caxboxylic acid, 24 parts of borax and 17.2 parts of ß-naphthylamine are heated to boiling under reflux, until no more unchanged 1-chloroanthraquinone-2-caxboxylic acid is present. the further work-up takes place as indicated above.

Instead of the condensing agents mentioned in the previous examples can also others, such as B. potassium bisulfate, phthalic acid, benzoic acid, arsenic Use acid, etc.

Claims (1)

PATENT CLAIM 'method for the representation of vat dyes Anthraquinone series, consisting in that 1-chloroanthraquinone-2-carboxylic acids with Arylamines in suitable solvents in the absence or in the presence of condensing agents condensed into acridones in one operation.