Polymers from 1,3-dipole addition reactions. The nitrilimine dipole from tetrazoles

Polymers containing pyrazole and triazole units in the polymer chain were obtained through the 1,3-dipolar addition reaction of bisnitrilimines generated from tetrazoles with diynes and dinitrile dipolarophiles. The reaction of 2,2′-diphenyl-5,5′-m- and p-phenyleneditetrazole with the dipolarophiles m- and p-diethynylbenzene, terephthalonitrile, tetrafluoroterephthalonitrile, perfluoroglutarylnitrile, and 4,4′-dicyanobiphenyl gave a series of thermally stable polymers of high molecular weight. The polypyrazoles were soluble in acid and in some cases in chlorobenzene or 1,2,4-trichlorobenzene and had intrinsic viscosities as high as 1.67, while the polytriazoles were soluble in 1,2,4-trichlorobenzene and chlorobenzene, but not in acid, and had viscosities ranging up to 0.40. The thermogravimetric analyses of the finely powdered polymers showed breaks near 500°C in air and nitrogen atmospheres.