Reversible, Nondegradative Conversion of Crystalline Aromatic Poly(ether ketone)s into Organo-Soluble Poly(ether dithioketal)s

Crystalline aromatic poly(ether ketone)s such as PEEK and PEK may be cleanly and reversibly derivatized by dithioketalization of the carbonyl groups with 1,2-ethanedithiol or 1,3-propanedithiol under strong acid conditions. The resulting 1,3-dithiolane and 1,3-dithiane polymers are hydrolytically stable, amorphous, and readily soluble in organic solvents such as chloroform and THF and are thus (unlike their parent polymers) easily characterized by gel permeation chromatography (GPC). GPC analysis of a range of derivatized PEEK samples using light-scattering detection revealed, in some instances, a bimodal molecular weight distribution with a small but potentially significant (and previously undetected) very high-molecular-weight fraction.