Sustainable polyacetals from isohexides

Abstract

A single step synthetic protocol to access a small family of renewable diacetals was established. The resultant chiral diacetals are valuable building blocks in pharmaceuticals and materials science. To demonstrate their synthetic competence, isohexide-diacetals (2a–c) were subjected to acetal metathesis polymerization and the corresponding polymers (poly2a–c) were isolated as white solids with molecular weights in the range 3200–27 600 (g mol⁻¹). The semi-crystalline polymers displayed glass transition temperatures between 38–65 °C and melting temperatures in the range 103–156 °C. The isohexide derived polyacetals are stable under practical washing and rinsing conditions but degrade in slightly acidic media.