Patent GB-327711-A (GB)
Abstract: 327,711. Johnson, J. Y., (I. G. Farbenindustrie Akt.-Ges.). Oct. 29, 1928. The first Provisional Specification is divided on 327,702. Iodo-halogen organic compounds capable of being vatted are prepared by acting on iodo derivatives of organic compounds capable of being vatted with chlorine or bromine or agents supplying these in dissolving or suspending media and in presence of catalysts, if desired. The iodinated vattable organic substances may be treated simultaneously or successively with chlorine or bromine or agents supplying these to give substances containing all three halogens. Halogenating conditions must be chosen to avoid elimination of iodine by the entering halogen; generally an excess of halogenating agent and temperatures above 100‹ C. are to be avoided, but in cases where halogenation is difficult a large excess of halogenating agent employed at a lower temperature may be effective. Advantageous chlorination conditions comprise the use of nitrobenzene, trichlorbenzene, sulphuric acid, oleum and chlorsulphonic acid as suspending media, of sulphuryl chloride as halogenating agent, of temperatures below 100‹ C., and iodine and sulphur are suitable catalysts. For bromination the same suspending media may be advantageously used or the iodinated compound treated with liquid bromine or bromine vapour in absence of any media, and antimony and iron are suitable catalysts. By selecting conditions iodo derivatives of anthraquinone, anthanthrone, pyranthrone, msbenzodianthrone, ms-naphthodianthrone, allo-msnaphthodianthrone, ms-anthradianthrone, dibenzanthrone, pyrazolanthrone, acridones, thioacridones and their isomers and substitution products may all be further halogenated. The products may be purified by crystallization from high-boiling solvents, by treatment with oxidizing agents, or by means of the oxonium sulphates which separate from an aqueous sulphuric acid solution. The following products, which are dyes are prepared in examples, dyeing shades being indicated in brackets:-(1) a chloroiodoanthanthrone (scarlet-red) and a bromoiodoanthanthrone (scarlet-red) from the iodo derivative obtained from monoaminoanthanthrone (Specification 325,797); (2) a chloroiodoanthanthrone and chlorbromiodoanthanthrone (orange) from the iodo derivative prepared according to Specification 327,702; (3) a bromoiodo-3.4.8.9-dibenzpyrene-5- 10-quinone (orange) from the iodo derivative obtained by nitrating the dibenzpyrenequinone in nitrobenzene, reducing, diazotizing, and a Sandmeyer replacement; (4) a chloroiodo-3.4.8.9-dibenzpyrene-5-10-quinone (orange-yellow) from the iodo derivative obtained according to Specification 327,756; (5) a bromoiodopyranthrone (orangered) and a chlorbromiodopyranthrone (orange-red) from the iodo derivative prepared according to Specification 327,702; (6) a chloroiodopyranthrone (orange) from the iodo derivative obtained by nitrating pyranthrone in nitrobenzene, reducing, diazotizing and a Sandmeyer replacement (Specification 325,250); (7) a chloroiododibenzanthrone (navy blue) and a chlorbromiododibenzanthrone (reddish-blue) from the iodo derivative prepared by nitrating dibenzanthrone in nitrobenzene at low temperatures, reducing the mononitro body, diazotizing and a Sandmeyer replacement; (8) a chlorbromoiodoisodibenzanthrone (blue-violet) from the iodo derivative prepared by the process stated above for iododibenzanthrone; (9) a chloroiodobenzanthrone-pyrazolanthrone (blue) and a bromiodobenzanthrone-pyrazolanthrone (blue) from the iodo compound obtained by alkali fusion of Bz.1 : N-benzanthrone-pyrazolanthrone, nitration in glacial acetic acid, reduction, diazotization and a Sandmeyer replacement; (10) a chloroiodothioindigo (blue-red) and a bromoiodothioindigo (violet) from 7.7<1>-diiodothioindigo prepared from the corresponding nitro compound (Specification 8162/07) by reduction, diazotization and a Sand meyer replacement. Specification 327,756, also is referred to.