Synthesis and degradabilities of polyesters from 1,4:3,6‐dianhydrohexitols and aliphatic dicarboxylic acids

Six different polyesters ( 6a–6c and 7a–7c ) were prepared by the bulk polycondensations of the respective combinations of 1,4:3,6‐dianhydro‐D‐glucitol ( 3 ) and 1,4:3,6‐dianhydro‐D‐mannitol ( 4 ) with succinyl dichloride ( 5a ), glutaryl dichloride ( 5b ), and adipoyl dichloride ( 5c ) at 140–180°C. Polyesters having number average molecular weights up to 2.6 ×10 4 were obtained in high yields. Only polyester 7a based on 4 and 5a was partially crystalline, whereas all the other polyesters were amorphous. Thin films of these polyesters except that of 7a were spontancously hydrolyzed in a neutral phosphate buffer solution at 50°C, whereas they were reluctant to be hydrolyzed at 27°C. The polyesters were more or less degraded at 27°C by treatment with an activated sludge or by prolonged burial in soil.