GB1075166A - Fluorinated aromatic diamides - Google Patents

Abstract

The invention relates to diamides of the formula A-Ar-A, in which Ar denotes a divalent aromatic structure containing one or more aromatic nuclei and A denotes an amide grouping of the formula R.CO.N(R1)- or R.N(R1).CO- attached to a nuclear carbon atom of Ar, R denoting a monovalent aromatic radical containing one or more aromatic nuclei and R1 denoting hydrogen or a monovalent aromatic radical containing one or more aromatic nuclei and the product containing at least one fluorine atom as a nuclear substituent. The diamides may be made by reacting a diamine of the formula R1NH-Ar-NHR1 or a monoamine of the formula R.R1.NH with, respectively, a monocarboxylic halide of the formula R.CO.X or a dicarboxylic halide of the formula X.CO.Ar.CO.X, in which X denotes a halogen atom, it being stipulated that, when R1 denotes an aromatic radical, at least one of the nuclei to which each nitrogen atom is linked should be free from fluorine. Alternatively, when both R and R1 denote aromatic radicals, the products may be prepared by reacting an alkali-metal derivative of a di-secondary amine of the formula M.(R1)N-Ar-N(R1)M or an alkali-metal derivative of a mono-secondary amine of the formula RR1NM, in which M denotes an alkali-metal atom, with, respectively, a monocarboxylic halide R.CO.X or a dicarboxylic halide X.CO.Ar.CO.X. Suitably, Ar is a phenylene, fluorophenylene, biphenylene or fluorobiphenylene radical, R is a phenyl, fluorophenyl, biphenylyl or fluorobiphenylyl radical and R1 is the same as R, unless it is hydrogen, but any of Ar, R and R1 may also denote an optionally fluorinated naphthalene nucleus or two optionally fluorinated benzene nuclei linked through an intermediate atom or group, e.g. an alkylene, carbonyl or sulphonyl group. In typical examples of reactions effected with aromatic monoamines or diamines, (1) m-phenylene diamine and pentafluorobenzoyl chloride yield 1,3 - bis - (pentafluorobenzamido) benzene, (2) 4,41-diaminooctafluorobiphenyl and pentafluorobenzoyl chloride yield 4,41-bis-(pentafluorobenzamido) octafluorobiphenyl, (3) aniline and tetrafluoroterephthaloyl chloride yield tetrafluoroterephthaloyl dianilide and (4) pentafluoroaniline and tetrafluoroisophthaloyl chloride yield tetrafluoroisophthaloyl di-(pentafluoroanilide). In typical examples of the use of alkali-metal compounds of aromatic monoamines or diamines, (1) decafluorodiphenylamine is treated with butyl lithium and the product is reacted with tetrafluoroterephthaloyl chloride to yield N,N,N1,N1-tetra-(pentafluorophenyl) tetrafluoroterephthalamide and (2) N,N1 - bis - (pentafluorophenyl) tetrafluorop-phenylene diamine is treated with sodium hydride and the product is reacted with pentafluorobenzoyl chloride to yield N,N1-bis-(pentafluorophenyl) - 1,4 - bis - (pentafluorobenzamido) tetrafluorobenzene. A number of other products of the invention are specified.