Synthesis and Characterization of Amphiphilic Copolymers with Zwitterionic and Cardanol Moieties for Antifouling and Antibacterial Coating Applications

Abstract

A series of copolymers [PSH#s, where # means a mol % of sulfobetaine methacrylate (SBMA) unit in the polymers] with zwitterion and cardanol moieties were synthesized via free radical polymerization of 2-(dimethylamino)ethyl methacrylate (DMAEMA) and plant-derived monomer, 2-hydroxy-3-carbonylpropyl methacrylate (HCPM), followed by betainisation with 1,3-propane sultone. Cross-linked PSH# (PSH#C) films were prepared through spin-coating or drop-casting method and then UV light irradiation, and their surface properties were investigated. The PSH#C films showed high transparency to the visible light region, and a water static contact angle of their surfaces decreased when the amount of hydrophilic SBMA unit in the copolymers increased. Antifouling characteristics against both Escherichia coli (E.coli) and bovine serum albumin (BSA) of the PSH#C films were enhanced as the SBMA moiety in the copolymers increased. All of the PSH#C films were non-cytotoxic against Human dermal fibroblasts (HDFs) and the amount of HDFs attached to the surfaces decreased when the zwitterion moiety in the PSH increased. Furthermore, the PSH#C films exhibited high antibacterial property against E.coli because of a presence of the bactericidal HCPM moiety in the PSH. Consequently, it was demonstrated that the PSHs have good anti-adhesion and bactericidal characteristics due to the SBMA and HCPM respectively, and non-cytotoxicity. Especially, PSH42 having proper amount of the SBMA and HCPM units exhibited excellent antifouling and antibacterial properties, and is expected to be a candidate for coating material in anti-biofouling fields.