Thermo-reversible Diels-Alder polymerization of difurfurylidene trehalose and bismaleimides

摘要

Difurfurylidene trehalose (DFTreh)was synthesized by the reaction of trehalose and furfural,both of which are renewable resources.Diels-Alder polymerization of DFTreh with 4,4'-bismaleimidodiphenylmethane (BMIDP)or 1,6-bismaleimidohexane (BMIH)at 40-70 deg C in DMF afforded novel trehalose-based linear polymer with M_w of ca.15,000 in good yield.The retro Diels-Alder degradation of the obtained polymers in DMF rapidly progressed at ca.140 deg C to afford the corresponding monomers quantitatively,as is obvious from the GPC analysis.In case of DFTreh/BMIDP,the prolonged maintenance of the degraded mixture at 140 deg C resulted in the homo-polymerization of the formed BMIDP.