Phosgene-Free Syntheses and Hydrolytic Properties of Water-Soluble Polyhydroxyurethanes with Ester–Carbonate–Ether Structures in Their Main Chains

Abstract

Three types of bifunctional 6-membered cyclic carbonates bearing ester, acyclic carbonate or ether moieties have been derived from nonexpensive trimethylolpropane or di(trimethylolpropane) through phosgene-free routes and used for the polyaddition reaction with 1,3-diaminopropane to design polyhydroxyurethanes (PHUs) containing the corresponding linkages in their main chains. Furthermore, these PHUs have been chemically modified via their OH groups to afford water-soluble PHUs (WSPHUs) and characterized for their hydrolytic properties at different pH conditions. Carbonate and ester bonds in these WSPHUs are easily hydrolyzed under basic conditions and their hydrolytic rates depend on their main chain structures; WSPHUs bearing carbonate structures are degraded faster than WSPHUs with ester linkages, while WSPHUs having ether bonds are slowest hydrolyzed. Moreover, the hydrolytic rates of these WSPHUs can be modulated by the copolymerization of these monomers at different feed ratios. (Figure presented.).