Copolymerization of photocrosslinkable anhydride monomers for use as a biodegradable bone cement

A multifunctional anhydride monomer, methacrylated sebacic anhydride (MSA), was synthesized and copolymerized with methacrylic anhydride via photoinitiated polymerization to form highly crosslinked, degradable networks. This material system was investigated as a potential degradable bone cement. Several aspects were examined, including curing characteristics, degradation rates and mechanical properties. These copolymer networks reached high double-bond conversions on clinically acceptable time scales (<5 min). Furthermore, these divinyl monomer copolymerizations exhibit features of classical crosslinking polymerizations, including autoacceleration, autodeceleration and limited double-bond conversion. Additionally, the networks degrade via a surface erosion mechanism by which the degradation rate can be controlled through varying the degree of oligomerization of the multifunctional monomer backbone, varying the copolymer precursor composition and changing the monomer backbone chemistry. Finally, the copolymer was found to have improved mechanical properties over homopolymerized MSA. Compressive strengths as high as 78 +/- 5 MPa were attained with a 70/30 wt% MSA/methacrylic anhydride copolymer, which are comparable to measured (91 +/- 7 MPa) and literature (approx. 100 MPa) values for conventional poly(methyl methacrylate) bone cement.