HIGH TEMPERATURE POLYMERS FROM 1,3-DIPOLAR ADDITION REACTIONS.

The synthesis of N-(3-pyridyl)-sydnone has been effected by the dehydration of N-nitroso-N-(3-pyridyl)-glycine. The synthesis of 3-phenylsydnone-4-carboxylic acid has been carried out by lithiation and carbonation of 3-phenylsydnone and this acid has been converted to the acid chloride. The disydnone 4,4'-bis(3-phenylsydnonyl)sulfone has been prepared from the lithium salt of 3-phenylsydnone. The 1,1'-diphenyl-3, 3'-m-phenylene-delta 2-pyrazoline has been synthesized. The dinitrilimine precursor, 5,5'-p-phenylene-ditetrazole, has been synthesized by the reaction of terephthalonitrile with sodium azide. The polymerization of p-phenylene-3,3'-disydnone with m-divinylbenzene to yield poly(1,1'-p-phenylene-3,3'-m-phenylene-di-delta 2-pyrazoline) has been effected. A series of polymerizations with terephthaloylphenylhydrazide chloride in which the monomer balance was varied has been carried out. The polymerization of 2,2'-diphenyl-5,5'-p-phenyleneditetrazole with 4,4'-dicyanobiphenyl has afforded poly(1,1'-diphenyl-3,3' -p-phenylene-5,5'-p-biphenylene-ditriazole). (Author)