Versatile sugar derivatives for the synthesis of potential degradable hydrophilic-hydrophobic polyurethanes and polyureas

Biodegradable polymers obtained from renewable natural sources are currently receiving increasing attention because they are an alternative to the traditional petroleum-based plastics. In the present communication we describe the synthesis of the diol monomers 2,3,4-tri-O-benzyl-L-arabinitol (ABnOH) and 2,3,4-tri-O-benzylxylitol (XBnOH), and the diamino monomers 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzyl-L-arabinitol (ABnNH(2)) and 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-benzylxylitol (XBnNH(2)), which can be used in the preparation of new potentially biodegradable sugar-based polymers. As an example, we describe the synthesis and characterization of a polyurethane [PU-(ABnOH-HMDI)] and a polyurea [PUR-(ABnNH(2)-HMDI)] by poly addition reaction of ABnOH and ABnNH(2) with 1,6-hexamethylene diisocyanate.