GB434027A - Manufacture of new dyestuffs of the pyrene series - Google Patents

Abstract

Coloured pyrene quinone derivatives are obtained by causing 2 : 5 : 7 : 10-tetrachlorpyrene-3 : 8 quinone (obtainable by the process of Specification 414,230) to react with ammonia, a primary aliphatic, or a primary or secondary aromatic amine, advantageously in presence of an organic solvent. One or more chlorine atoms may be replaced, singly or in turn, until they are wholly replaced by amino groups. The products obtainable may have the following structures <FORM:0434027/IV/1> in which the R's represent the amino or substituted amino residues corresponding to the amine used. The halogen atoms in periposition to the CO groups react most readily. Most of the products are dyes for cotton, and some may be converted into leuco-sulphuric esters and used according to known methods. According to examples, tetrachloropyrenequinone is heated with aniline, p-toluidine, b -naphthylamine, p-aminodiphenyl, a -aminoanthraquinone, anthranilic acid or ethyl ester, aminosalicylic acid, ammonia, methylamine, and ethylamine to give the corresponding substituted mono - amino - trichloropyrenequinones; substituted diamino-dichloropyrenequinones corresponding to ammonia, aniline, p - anisidine, a and b - naphthylamine are obtained with the use of further quantities of the amines, and condensing agents, and a tetra-anilinopyrenequinone may be obtained with aniline. Samples have been furnished under Sect. 2 (5) of products obtained by condensing (I) tetrachloropyrenequinone with m-chloraniline to give a di-m-chloranilinopyrenequinone; (II) p - diphenylaminotrichloropyrenequinone with aniline to give a p-phenylamino-anilino-dichloropyrenequinone; (III) dichlordianilinopyrenequinone with a -amino-anthraquinone; (IV) tetrachloropyrenequinone with N-methylaniline; (V) mono - N - methylanilinotrichloropyrenequinone with N-methylaniline to give a di-N-methylaninodichloropyrenequinone. The Specification as open to inspection under Sect. 91 refers also to the condensation with secondary aliphatic amines. This subject-matter does not appear in the Specification as accepted.