Patent GB-467770-A (GB)
Title: The manufacture of nitrogenous condensation products of the anthrone series
IPC: C09B3/00
Filed: 1936-06-24
Abstract: Nitrogenous condensation products of the anthrone series are manufactured by condensing, at a temperature below 100 DEG  C., anthrone derivatives which do not contain primary or secondary amino groups and which have the general formula  <FORM:0467770/IV/1> where R is a carbocyclic ring or a heterocyclic ring containing no free cyclic imino group, the total number of rings of the whole molecule being not more than seven, with a primary amine of a vattable ring system in the presence of a strongly alkaline acting condensing agent, e.g. caustic alkali or sodamide, advantageously in the presence of a diluent, e.g. pyridine, quinoline or nitrobenzene, and if desired in the presence of an oxidizing agent, e.g. by blowing in air.  Suitable starting materials are N-alkyl-anthrapyridones, N - alkylpyrazolanthrones, benzanthrones, phthaloylbenzanthrones, anthanthrones, dibenzoperylenequinones and dibenzopyrenequinones. The products may be used for dyeing fibres or as intermediates for the production of dyestuffs.  In examples: (1) benzanthrone and 1-amino-5-benzoylaminoanthraquinone are stirred in the cold with pyridine and caustic potash while passing air through the mixture; (2) Bz1-bromobenzanthrone is stirred in the cold with 1-aminoanthraquinone or 1 - amino - 5 - benzoylaminoanthraquinone in the presence of pyridine and caustic potash; (3) N-methylanthrapyridone and 1-aminoanthraquinone are similarly condensed at 50 DEG  C.; (4) Bz1-Bz2-phthaloylbenzanthrone and 1-aminoanthraquinone are condensed as in (2); (5) anthanthrone and 1-aminoanthraquinone are stirred at 50 DEG  C. with pyridine and sodamide; the product dyes cotton corinth shades; if the sodamide is replaced by caustic potash and a larger amount of 1- or of 2-aminoanthraquinone is employed, there are obtained products which dye cotton reddish corinth and reddish brown shades respectively; (6) anthanthrone and 1-amino-4-benzoylaminoanthraquinone are milled with pyridine and caustic potash, yielding products containing the anthraquinone residue once or twice and dyeing cotton grey and bluish grey shades respectively; (7) dibromanthanthrone and 1-aminoanthraquinone are stirred at 50--60 DEG  C. with pyridine or nitrobenzene and caustic potash; the product dyes cotton violet-brown shades; (8) dibenzoperylenequinone and 1-amino-4-benzoylaminoanthraquinone are stirred in the cold with pyridine and caustic potash; the product dyes cotton violet shades; 4 : 5 : 8 : 9-dibenzopyrenequinone and 1-amino-5-benzoylaminoanthraquinone may be similarly condensed, the product dyeing cotton corinth shades.  Specifications 260,998, 275,283, [both in Class 2 (iii)], and 405,949 are referred to.  The Specification as open to inspection under Sect. 91 comprises generally the condensation of any compounds of the general formula given above, in which R is any carbocyclic or heterocyclic ring, with primary amines of vattable ring systems in the presence of alkaline condensing agents.  Anthrapyridones are additionally specified as starting materials.  This subject-matter does not appear in the Specification as accepted.