Synthesis and properties of novel segmented polyurethanes containing alkyl phosphatidylcholine side groups

In this article, we report the synthesis and properties of novel segmented polyurethanes containing alkyl phosphatidylcholine side groups. Alkyl phosphatidylcholine groups were attached to the hard blocks of the polyurethanes. A novel diol, 9-(2-hydroxy-1-hydroxymethyl-1-methyl-ethylcarbamoyl)-nonyl-phosphatidylcholine (HDEAPC), was synthesized and characterized by FTIR, 1H-NMR and mass spectroscopy. Two types of polyurethanes, poly(ether urethane)s and poly(carbonate urethane)s, containing alkyl phosphatidylcholine side groups were synthesized using methylenebis(phenylene isocyanate) (MDI), polytetramethyleneoxide (PTMO), poly(1,6-hexyl-1,5-pentylcarbonate) diol (PHPCD), 1,4-butanediol (BDO) and HDEAPC. The obtained phosphatidylcholine polyurethanes had relatively high molecular weights and good mechanical strength, as characterized by GPC and Instron. XPS and contact angle studies revealed that there was enrichment of alkyl phosphatidylcholine side groups near the surface of the polyurethanes. Biocompatibility was evaluated by protein adsorption using conventional polyurethanes as references. The surface of phosphatidylcholine poly(carbonate urethane)s effectively suppressed protein adsorption.