Synthesis and Characterization of Polyamide of Trans-4-hydroxy-L-proline used as Porogen Filler in Acrylic Bone Cement

Abstract

The aim of this study was to synthesize on a larger scale, an experimental polyamide based on an amino acid of trans-4-hydroxy-L-proline. The polyamide of trans-4-hydroxy-L-proline has been used as porogen filler (i.e., a hydrophilic pore generating material) in nondegradable acrylic bone cement. In in vitro studies, this hydrophilic filling component has been shown to form porosity within the acrylic bone cement in an aqueous environment. The formation of in situ porosity in the acrylic polymer matrix is believed to improve the fixation between the cement and the living bone. Namely, a porous structure can support bone ingrowth and strengthen the mechanical connection between the acrylic bone cement and the bone. The monomer, trans-4-hydroxy-L-proline methyl ester, was prepared from trans-4-hydroxy-L-proline by means of two steps, and the monomer was then polymerized to polyamide of trans-4-hydroxy-L-proline. The polymerization was carried out using a melt polycondensation method. The molecular weights (Mψ) of the produced polyamides were between 1800 and 3600. The products were characterized by FTIR and 1H-NMR spectroscopy.