Patent GB-323750-A (GB)
Title: A process for the manufacture and production of valuable substitution products of the anthanthrone series
IPC: C09B3/64
Filed: 1928-08-25
Abstract: 323,750. Johnson, J. Y., (1. G. Farbenindustrie Akt.-Ges.). Aug. 25, 1928. Anthanthrone derivatives.- Mononitroanthanthrones are prepared by treating anthanthrone and derivatives thereof with strong nitric acid in a high boiling organic solvent or diluent which is present in quantities at least double, and preferably ten times that of the acid. Suitable solvents are nitrobenzene, or its homologues, and chlormated benzenes. The monaminoanthanthrones are prepared by reduction of the mononitro derivatives, for instance by means of alkali sulphide, hydrosulphite, or hydrazine. New dyestuffs are obtained by replacing one or both reactive hydrogen atoms in these amino compounds by negatively substituted organic compounds which comprise aliphatic, cycloaliphatic, aromatic and heterocyclic compounds containing at least one negative substituent and which may be further substituted. The condensation products with aroyl halides substituted in the mposition, for example, by a methoxy group, are partciularly valuable. These condensations are effected in a high boiling organic medium such as nitrobenzene or its homologues, or trichlorbenzene, and if desired, in presence of acid fixing agents such as sodium acetate, potassium carbonate, and of catalysts such as copper, copper salts, mercuric oxide, aluminium. Azomethanes with good vatting properties are obtained by treating these amino derivatives with aldehydes. The following products are prepared in examples, the dyeings on cotton being indicated in brackets :- mononitroanthant-hrone (blue-grey); monoaminoanthanthrone (blue-grey, and also dyes acetate silk this shade); mononitrobromanthanthrone (grey) from the dibromo derivative prepared by treating anthanthrone in nitrobenzene or oleum with bromine; mononitro-monohydroxyanthanthrone (violet-grey) from the monomethoxy derivative obtained by methylating the hydroxy anthanthrone derived from the diazotized amine; the mononitro derivatives of the monohalogen anthanthrones obtained by the Sandmeyer reaction from the monoamino derivatives, and of the dichloranthanthrone obtainable by chlorination of anthanthrone in nitrobenzene or oleum, are also mentioned; the condensation products of monoaminoanthanthrone with isophthalyl chloride (red), m-methoxybenzoyl chloride (red), benzoyl chloride (yellow-red), 1-chloranthraquinone-2-carboxylic acid chloride (brown-red), 1-aminoanthraquinone-2-carboxylic acid chloride (red), 2-chloranthraquinone (grey-violet), 1-chloranthraquinone (grey-violet), dibromanthanthrone (brown), methyl ester of p-toluene sulphonic acid (grey-blue), ochlorbenzaldehyde (raspberry red) 1-aminoanthraquinone-2-aldehyde (blue-red); cyanuryl chloride (1 mol.) (blue-red), (<1>/3 mol.) (violet), and octabromcyclohexane (grey) prepared by brominating cyclohexane; the condensation products of monaminoanthanthrone with p-chloro- or pbromobenzoyl chloride, monobromo- or mononitroanthranthrone and halogenalkyl esters of ptoluene sulphonic acid are also mentioned. Specifications 285,502, 286,669, 307,364 and 318,180 are referred to.