Polyesters containing bicyclo[2.2.2]octane and bicyclo[3.2.2]nonane rings

Abstract
Polyesters containing bicyclo[2.2.2]octane and bicyclo[3.2.2]nonane rings are prepared from 1,4‐bis(carboethoxy)bicyclo[2.2.2]octane, 1,4‐bis(hydroxymethyl)bicyclo[2.2.2]‐octane and the 1,5‐disubstituted bicyclo[3.2.2]nonane analogs. These polyesters are compared to the related polymers containing 1,4‐phenylene and trans‐1,4‐cyclohexylene rings in terms of their melting point, thermal stabilities and oxidative stabilities. The lower symmetry of the bicyclo[3.2.2]nonane ring produces lower‐melting polymers than the other ring systems. The remaining three rings are approximately equivalent in their effect on the melting point of a polymer provided that no more than one bicyclo[2.2.2]octane ring is present per polymer repeat unit. Two such rings produce a highermelting polymer than any other combination. Both the thermal and oxidative stabilities of the polyesters is improved by the presence of the bicyclo rings. This is attributed to the rings providing an approximation of a ladder polymer.

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