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

Ring-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.     

Macromolecular synthesis from saccharic lactones. Polyaddition of D-glucaro- and D-mannaro- 1,4:6, 3-dilactones with diisocyanates and hydrolyzability of the resulting polyurethanes having dilactone rings in the main chains

Polyaddition of saccharic acid dilactones prepared from D-glucose and D-mannitol, D-glu-caro-, and D-mannaro-1,4:6,3-dilactones ( 1 and 2 , respectively), with hexamethylene di-isocyanate ( 3a ) and methyl (S)-2,6-diisocyanatocaproate ( 3b ) was carried out by using dibutyltin dilaurate as a catalyst at 50, 25, and 0°C to give polyurethanes ( 4 and 5 ) having dilactone moieties in the main chains. The resulting polymers were found to decompose easily in phosphate buffers under neutral or slightly basic conditions (pH 7 or 8). Therefore, the polyurethanes may be used as novel degradable polymeric materials. © 1995 John Wiley & Sons, Inc.