Macromolecular synthesis from saccharic lactones. Ring‐opening polyaddition of D‐glucaro‐ and D‐mannaro‐1,4:6,3‐dilactones with alkylenediamines

Abstract

AbstractRing‐opening polyaddition of a saccharic acid dilactone prepared from D‐glucose, D‐glucaro‐1,4 : 6,3‐dilactone, with several alkylenediamines proceeded at room temperature with no catalyst. The resulting new polyamides carrying many pendant hydroxyl groups, poly(alkylene D‐glucaramide)s, were more amorphous and hydrophilic than the corresponding nylons having no hydroxyl groups, and were hydrolyzed more easily than the latter in an acidic condition. The ring‐opening ability of D‐mannaro‐1,4:6,3‐dilactone, which was another saccharic acid dilactone obtained from D‐mannitol, was found to be lower than that of the D‐glucaric analogue. © 1993 John Wiley & Sons, Inc.