Preparation, characterization, and properties of poly(thioether imide)s from isomeric bis(chlorophthalimide)s and bisthiophenols

Abstract

A series of isomeric poly(thioether imide)s (PTIs) containing thioether linkages were prepared by aromatic nucleophilic substitution reaction of isomeric bis(chlorophthalimide)s (BCPIs) and bisthiophenols. The glass transition temperatures ( Tgs) of the isomeric PTIs were 190–264°C, the 5% weight loss temperature ( T5%) reached up to 441–508°C under nitrogen and 472–520°C in air atmospheres, respectively. It was found that the Tg values of the PTIs from three isomeric BCPIs with the same bisthiophenol increased in the order of 4,4′-BCPI < 3,4′-BCPI < 3,3′-BCPI, while the T5% values gradually decreased in the order of 4,4′-BCPI > 3,4′-BCPI > 3,3′-BCPI. Flexible films that could be cast from the polymer solutions exhibited good mechanical properties with tensile strengths of 91–121 MPa, elongations at break of 8–12%, and tensile moduli of 2.2–2.6 GPa. The minimum melt viscosity of isomeric PTIs decreased with increasing the content of asymmetric 3,4′-substituted phthalimide unit, and the PTI (2c) showed the lowest melt viscosity about 760 Pa·s at 264°C among these isomeric polymers.