Synthesis of imidazolium-containing mono-methacrylates as polymerizable antibacterial agents for acrylic bone cements

Abstract

With the aim to prepare antibacterial acrylic bone cements, a series of imidazolium-containg mono-methacrylates with N-alkyl chain length varied from 10 to 18 (MEIM-x) were synthesized as polymerizable antibacterial agents through a two-step reaction. The structures of the monomers were confirmed by 1H NMR. Methyl methacrylate in the liquid compoent of cements was partially replaced by MEIM-x to prepare bone cements with 5wt% of MEIM-x. Properties of prepared cements like antibacterial activity, doughing time, curing parameters including maximum temperature (Tmax) and setting time (tset), flexual strength (FS) and modulus (FM), compressive strength (CS) and fluid uptake (FU) in Ringer's solution were investigated. Acrylic bone cement without any MEIM-x was used as control. Compared with the control cement, MEIM-x-containing cements had shorter doughing time, lower Tmax, same or longer tset, and higher FU. Though MEIM-x could endow cements with strong antibacterial activity, it could reduce mechanical properties of bone cements. Therefore, further study should be taken to optimize the content of MEIM-x in cement which could supply sufficient antibacterial activity and maintain mechanical performance.