In this work, four isohexide-derived isomeric dianhydrides were synthesized through a four-step procedure using isohexide and chloro-N-phenylphthalimides as the starting materials. The one-step solution polymerization of these dianhydrides with petroleum- or bio-based diamines enabled the synthesis of poly(ether imide)s (PEIs), which had viscosities of 0.41 to 2.40 dL∙g-1. The isohexide-derived PEIs were characterized based upon their solubility and their thermal, mechanical, and optical properties. The results showed that most of the isohexide-derived PEIs possessed comparable glass transition temperatures (Tg), tensile strengths, and moduli to petroleum-based PEIs. However, the thermo-oxidative stability of the PEIs was found to be lower than that of the common petroleum-based PEIs. Moreover, the PEIs displayed good optical activity, which originated from their unique chiral isohexide moieties. The isomeric effects of dianhydride monomers on the properties of the resulting PEIs were comparatively studied. The results suggested that the corresponding 4,4'-linked PEIs possessed lower Tg, higher mechanical properties, and higher specific rotations compared to 3,3'-linked polymers. Meanwhile, the polyimides with isomannide residue displayed higher Tg and more specific rotations than the corresponding polymers with isosorbide residue. These results contributed to more restricted rotations of phthalimide segments in 3,3'-linked or isomannide containing polyimides.
Keywords: isohexides; isomeric dianhydrides; poly(ether imide)s.