A facile synthesis of a novel polyacetal containing trehalose residue in the main chain

A novel polyacetal containing α,α-d-trehalose residue in the main chain was successfully synthesized by the reaction of α,α-d-trehalose with terephthalaldehyde bis(dimethyl acetal) in the presence of p-toluenesulfonic acid. As a result of examination of reaction condition, weight-average molecular weight (Mw) of the polyacetal ranged from 2000 to 8500 when measured by GPC. The polyacetal was soluble in dipolar aprotic solvents such as DMSO and DMF. The 1H-NMR and MALDI-TOF MS spectra revealed that the polyacetal is composed of the molecules terminated by glucopyranosyloxy group, dimethylacetal group, and aldehyde group generated by the hydrolysis of dimethyl acetal group. The polyacetal with Mw 8500 showed no glass transition temperature up to the decomposition temperature (325 °C).