Patent GB-255277-A (GB)
Title: Improvements in the manufacture and production of condensation products and dyestuffs of the benzanthrone series
IPC: C09B3/06
Filed: 1925-10-07
Abstract: 255,277. Johnson, J. Y., (Badische Anilin & Soda Fabrik). Oct. 7, 1925. Isodibenzanthrone dyes; 2: Bz1<1>-dibenzanthronyl and its derivatives.- Isodibenzanthrone dyes are obtained by treating with alkaline condensing agents mixtures of Bz1-halogenbenzanthrones with benzanthrones having the Bz1-position free, the 2-positions of the benzanthrones must in each case be free; the benzanthrones are used in approximately equimolecular proportions, or the Bz1-halogen body may be in excess. As condensing agents mixtures of caustic alkalies with alkali alcoholates in the. presence of an inert diluent, or metal arylides are particularly suitable : oxygen should be excluded as far as possible. When the condensation is effected under more moderate conditions 2 : Bz1<1>-dibenzanthronyls are formed and mav be separated from any admixture of dyestuff by treatment with hydrosulphite in which they are insoluble; they can be converted into the isodibenzanthrone dyes by further treatment with acid or alkaline condensing agents. According to examples the following dibenzanthronyls and isodibenzanthrones are obtained :-(1) 2 : Bz1<1>-dibenzanthronyl from benzanthrone, Bz1-chlorbenzanthrone (Specification 20837/06), and sodium anilide or monomethylanilide in aniline, or caustic potash and ethyl alcohol in toluene at 10-15‹ C. : (2) 6- or 7-chlor-2 : Bz1<1>-dibenzanthronyl from 6- or 7- chlorbenzanthrone and Bz1-chlorbenzanthrone; (3) 6-methyl-2 : Bz1<1>-dibenzanthronyl from 6- methylbenzanthrone and Bz1-chlorbenzanthrone; (4) isodibenzanthrone from 2 : Bz1<1>-dibenzanthronyl and sodium-anilide or caustic potash and alcohol at 140‹ C.; (5) 6-methyl- or 6-chlor-isodibenzanthrone from 6-methyl- or 6-chlor-2:- :- Bz1<1>-dibenzanthronyl ; (6) a chlorinated isodibenzanthrone from 2 : Bz1<1>-dibenzanthronyl and a mixture of ferric and sodium chlorides: the use of aluminium chloride, or sulphuric acid of 80 per cent strength in the presence of mercury salts, leads to formation of isodibenzanthrone; (7) isodibenzanthrone from a mixture of Bz1 brom- or Bz1-chlor-benzanthrone with benzanthrone by treatment with sodium ethylate, sodium ethylate and caustic potash in xylene, or isopropyl alcohol and caustic potash in benzene; (8) 6-chlor- or 6-methyl-isodibenzanthrone from a mixture of 6-chlor- or 6-methylbenzanthrone and Bz1-chlorbenzanthrone (9) 6-ohlorisodibenzanthrone from a mixture of 6 : Bz1-dichlorbenzanthrone and benzanthrone; (10) 6-bromisodibenzanthrone from a mixture of 6-brom-Bz1 chlorbenzanthrone and benzanthrone; (11) 8- chlorisodibenzanthrone from a mixture of 8-chlorbenzanthrone and Bz1-chlorbenzanthrone, or 8 : - Bz1-dichlorbenzanthrone and benzanthrone; (12) 8 : 8<1>-dichlorisodibenzanthrone from 8 : Bz1-dichlorbenzanthrone and 8-chlorbenzanthrone. Halogenbenzanthrones. - 8-Chlorbenzanthrone is obtained by fractional crystallization of the chlorbenzanthrone obtained from glycerol and 1- chloranthraquinone according to Specification 7022/05. 6 : Bz1- and 8 : Bz1-Dichlorbenzanthrones are respectively obtained by treating 6- and 8-chlorbenzanthrones with sulphuryl chloride; by oxidation they yield respectively the 6- and 8-chloranthraquinone-1-carboxylic acids which after conversion into the acid amides can be transformed into 6- and 8-chlor-1-aminoanthraquinones. 6-Brom-Bz1-chlorbenzanthrone is obtained by brominating Bz-1-chlorbenzanthrone, or by chlorinating 6-brombenzanthrone with sulphuryl chloride. Specification 16271/10 also is referred to.