DE645964C - Process for the preparation of dyes and dye intermediates of the anthraquinone series - Google Patents

Description

Process for the preparation of dyes and dye intermediates the anthraquinone series. According to the procedure of the main patent 642 339 new Dyes and dye intermediates of the anthraquinone series obtained by that one such anthraquinone derivatives which on the nucleus in a, ß-positions one or more Thiazole rings attached as side rings don't contain linked to primary amines Ring systems can act in the presence of alkaline condensing agents. It has now been found that valuable dyes and dye intermediates can also be obtained the anthraquinone series can be achieved if one follows the procedure of the main patent the anthraquinone derivatives of the type identified there replaced by those that one or more optionally substituted on the anthraquinone nucleus in a, ß-positions Included pyridine rings attached.

The reaction probably proceeds in such a way that the amino group of the second reaction component bonds with a carbon atom of the pyridinoanthraquinone to form a secondary amine. The condensation product of i # a (N) -pyridinoanthraquinone and a-aminoanthraquinone probably has the following formula Since the reaction presumably takes place with the escape of hydrogen, it is advantageous, with the addition of a suitable oxidizing agent, e.g. B. with passage of air to work.

The products obtainable by the present process are mostly dyes which are characterized by very good boiling and chlorine fastness; they - should also be used as intermediate products "for the manufacture of other dyes. .... Example i 2 # 6 parts of i # 2 (N) -pyridinoantlirachine and z # 5 parts of ct-aminoanthraquinone are ° stirred in 40 parts of pyridine with 5 parts of powdered caustic potash for about 5 hours at 5o °. The condensation product formed is filtered off with suction and washed with a little pyridine and acidified water. The dried product can be obtained from higher-boiling organic solvents such as nitrobenzene in a nicely uniform crystallized form in the form of red needles. The product dissolves in concentrated sulfuric acid with blue, in 80 ° (oiger sulfuric acid with red color and provides, dyed from the vat, red colorations on cotton, which are characterized by very good boiling and chlorine fastness. The compound is identical to that in Example i, last paragraph, of patent 574c) 67.

If one replaces in the example above (read r # 2 (N) -Pyridinoanthraquinone by the corresponding amount of an i # 2 (\) - pyridinoanthraquinone, its Py-2 position is substituted by a 2 # 6-dichlorophenyl radical, a red one is obtained Dye, the shade of which is slightly shifted towards blue.

Example 2 .2-6 parts of i (N) 2-pyridinoanthraquinone and 2 # 5 parts a Aminoanthraquinone is mixed with 3o parts of alcohol and 3 parts of powdered caustic potash Boiled under reflux for 6 hours with stirring. The separated from the liquid and Rain washed out with water can be removed by stripping it with organic solvents, for example chlorobenzene, freed from any raw materials that may still be present will. The condensation product is obtained in crystallized form by dissolving from nitrobenzene. It dissolves in concentrated sulfuric acid with a pure blue color and delivers Cotton from a yellow-red vat red dyeings that are more yellow-safer than those of the dye described in Example i. Example 3 2 # 6 parts of i # 2 (N) -Pyridinoanthraquinone and 3 # 6 parts of i-amino-q.-benzoylaminoanthraquinone in 80 parts of pyridine stirred with 10 parts of caustic potash at 50 °. The liquid turns blue, and after The new condensation product has already formed in good yield about 1 hour. The precipitate formed is separated from the liquid and washed with a little Pyridine and water. The dried product dissolves in conc. sulfuric acid with a yellowish green color; from dichlorobenzene the condensation product becomes beautiful obtained uniformly crystallized. It is identical to that in Example 3, Para. i, of patent 574,967.

Example 2 # 6 parts of i # 2 (N) -pyridinoanthraquinone and 2 # 3 parts ß Aminoanthraquinone become finite together for 24 hours at ordinary temperature 10 parts of finely ground caustic potash in 6o parts of anhydrous pyridine. That The condensation product deposited in the form of an alkali salt is filtered off with suction and washed out. From the vat it delivers red dyeings on cotton.

Claims (1)

PATENTA1jSPRUCH Process for the preparation of dyes and dye intermediates of the anthraquinone series, characterized in that in the process of main patent 642 339 the anthraquinone derivatives of the type identified there are replaced by those which contain one or more optionally substituted pyridine rings in the a, ß positions in the anthraquinone nucleus .