High Tg bio-based aliphatic polyesters from bicyclic D-mannitol

The carbohydrate-based diol 2,4:3,5-di- O -methylene- D -mannitol (Manx) has been used to obtain aliphatic polyesters. Manx is a symmetric bicyclic compound consisting of two fused 1,3-dioxane rings and bearing two primary hydroxyl groups. In terms of sti ff ness, it is comparable to the widely known isosorbide, but it a ff ords the additional advantages of being much more reactive in polycondensation and capable of producing stereoregular polymers with fairly high molecular weights. A fully bio-based homopolyester (PManxS) has been synthesized by polycondensation in the melt from dimethyl succinate and Manx. The high thermal stability of PManxS, its relatively high glass transition temperature ( T g =68 ° C) and elastic modulus, and its enhanced sensitivity to the action of lipases point to PManxS as a polyester of exceptional interest for those applications where biodegradability and molecular sti ff ness are priority requirements. In addition, random copolyesters (PB x Manx y S) covering a broad range of compositions have been obtained using mixtures of Manx and 1,4-butanediol in the reaction with dimethyl succinate. All PB x Manx y S were semicrystalline and displayed T g values from − 29 to +51 ° C steadily increasing with the content in Manx units. The stress − strain behavior of these copolyesters largely depended on their content in Manx and they were enzymatically degraded faster than PBS.Peer Reviewe