Characterization of new acrylic bone cements prepared with oleic acid derivatives

Abstract

Acrylic bone-cement formulations were prepared with the use of a new tertiary aromatic amine derived from oleic acid, and also by incorporating an acrylic monomer derived from the same acid with the aim of reducing the leaching of toxic residuals and improving mechanical properties. 4-N,N dimethylaminobenzyl oleate (DMAO) was used as an activator in the benzoyl-peroxide radical cold curing of polymethyl methacrylate. Cements that contained DMAO exhibited much lower polymerization exotherm values, ranging between 55 and 62 °C, with a setting time around 16–17 min, depending on the amine/BPO molar ratio of the formulation. On curing a commercial bone cement, Palacos Rwith DMAO, a decrease of 20 °C in peak temperature and an increase in setting time of 7 min were obtained, the curing parameters remaining well within limits permitted by the standards. In a second stage, partial substitution of MMA by oleyloxyethyl methacrylate (OMA) in the acrylic formulations was performed, the polymerization being initiated with the DMAO/BPO redox system. These formulations exhibited longer setting times and lower peak temperatures with respect to those based on PMMA. The glass transition temperature of the experimental cements were lower than that of PMMA cement because of the presence of long aliphatic chains of both activator and monomer in the cement matrix. Number average molecular weights of the cured cements were in the range of 1.2 105. PMMA cements cured with DMAO/BPO revealed a significant (p<0.001) increase in the strain to failure and a significant (p<0.001) decrease in Young’s modulus in comparison to Palacos R, whereas ultimate tensile strength remained unchanged. When the monomer OMA was incorporated, low concentrations of OMA provided a significant increase in tensile strength and elastic modulus without impairing the strain to failure. The results demonstrate that the experimental cements based on DMAO and OMA have excellent promise for use as orthopaedic and/or dental grouting materials