Patent GB-190620837-A (GB)
Title: Improvements in the Manufacture and Production of Anthracene Compounds and of Colouring Matters therefrom.
Inventor: JOHNSON JAMES YATE
Filed: 1906-09-19
Granted: 1907-05-30
Abstract: 20,837. Johnson, J. Y., [Badische Anilin & Soda Fabrik]. Sept. 19. Halogen derivatives of benzanthrone and its derivatives.-Compounds containing a benzanthrone group are treated with halogeoizing-agents, in the presence or absence of a dissolving-agent or diluting- agent. The products contain one or more than one atom of the halogen according to the method of carrying out the reaction. In examples, benzanthrone, the sodium salt of benzanthrone-2-sulphonic acid, and benzanthrone-quinoline, are treated with agents such as bromine, chlorine, potassium chlorate and hydrochloric acid, and sulphuryl chloride. Suitable dissolving or diluting agents are water, glacial acetic acid, and nitrobenzene. The reactions, which are sometimes effected at a raised temperature, yield solid products, and these are filtered off, washed with various liquids, and in some cases recrystallized from organic solvents, such as nitrobenzene, glacial acetic acid, alcohol, xylene, &c. The following halogen derivatives are mentioned, viz. : monobrombenzanthrone [melting-point 170‹ C.], dibrombenzanthrone [m.p. 257‹ C.], monochlorbenzanthrone [m.p. 176‹ C.], monobrombenzanthrone-2-sulphonic acid, monobrombenzanthronequinoline [m.p. 298‹ C.], and two isomeric dichlorbenzanthrone [m.p. 218‹ C. and 269‹ C.], these latter being obtained together and separated by frictional crystallization from nitrobenzene ; the isomer having the lower melting-point is the more difficultly soluble. It is also stated that other benzanthrone sulphonic acids may be brominated or chlorinated, and that benzanthroneaniline may be chlorinated. Various properties of the above-mentioned bodies are given, such as their behaviour towards organic and inorganic solvents &c. The products are stated to differ from those described in Specification No. 7022, A.D. 1905, in that they contain at least one halogen atom in the benzanthrone ring, and yield dye-stuffs more easily, the dyeings being brighter and redder in shade than those described in the above-mentioned case. Dyes, artificial. - Colouring- matters, which dye vegetable fibres from alkali hydrosulphite vats, are obtained by heating the above-mentioned halogen derivatives with caustic alkali, or alkali alcoholates, either alone or in the presence of diluting agents or solvents. In one example, sodium alcoholate suspended in a finely divided gelatinous condition in xylene, prepared by the action of metallic sodium upon a mixture of absolute alcohol and dry xylene at a raised temperature and with the exclusion of moisture and carbon dioxide, is employed for reacting upon monochlorbenzanthrone. The colouring-matters from monochlor-, monohrom-, and dibrombenzanthrone appear to be identical and free from halogen when certain methods of preparation are employed, while in other cases the dibrom body is stated to yield a dye stuff containing bromide. The melts are worked up by dissolving, precipitating the dye-stuff, filtering, washing, &c., the particular products mentioned yielding blue to reddishviolet shades on cotton. The dyestuffs are stated to differ from those obtained by halogenating benzanthrone colouring-matters, as described in Specification No. 22,519, A.D. 1905, and from the colouring-matters described in Specification No. 16,538, A.D. 1904, and Nos. 3819 and 7022, A.D. 1905.