Chain extenders for polyesters. I. Addition-type chain extenders reactive with carboxyl end groups of polyesters

Effective chain extenders for linear polyesters were investigated among some bis-heterocycles, which were capable of coupling carboxyl terminals of the polyesters through addition reaction. Consequently, 2,2′-bis(2-oxazoline), 2,2′-bis(5,6-dihydro-4H-1,3-oxazine) and N,N′-hexamethylenebis(carbamoyl-2- oxazoline) were found to be the most effective chain extenders. Starting from a poly(ethylene terephthalate) (PET) having intrinsic viscosity ([η]) of 0.66 and carboxyl content (CV) of 46 eq/10⁶ g, one could obtain polyesters with [η] of above 1.0 and CV of below 5 eq/10⁶ g in the presence of the chain extenders. Typical reaction condition for the coupling of PET was heating PET under atmospheric nitrogen above its melting temperature with 0.5 mol % of a chain extenders only for several minutes. Bis-2-thiazolines showed no effect under the condition investigated, while in case of bis-2-imidazolines definite degradation was observed. Bis-N-acylaziridines and bisiminocarbonates resulted in some gell formation, indicative of side reactions.