Novel biodegradable amino acid containing anhydride oligomers for orthopedic applications

摘要

Novel synthetic biodegradable methacrylated anhydride oligomers (MAOs) based on methacrylated alaninyl maleamic acid (MAMA) and methacrylated aminocaproyl maleamic acid (MACMA) were synthesized and characterized. Injectable and in situ crosslinkable polymer networks were formulated by the copolymerization of MAOs with triethylene glycol dimethacrylate (TEGDMA). Furthermore, composites composed of MAOs, TEGDMA, and beta-tricalcium phosphate were prepared. The networks and composites were initiated by photopolymerization and redox polymerization, respectively. The initial compressive strength (CS) and diametral tensile strength (DTS) of these materials were determined and used to evaluate the effects of the MAO/TEGDMA ratios on the degradation behavior of the materials. The MAMA-based composites had initial DTS values of 5.7-17.1 MPa and CS values of 30.7-114.2 MPa. The MACMA-based composites had initial DTS values of 2.8-20.8 MPa and CS values of 19.1-119.5 MPa. During the course of degradation, the neat polymer resins lost 97 and 87% of their initial CS values after 6 months with 50/50 MAMA/TEGDMA and MACMA/TEGDMA ratios, respectively. The composite with a 25/75 MACMA/TEGDMA ratio showed a significant increase in CS after an initial decrease for 7 days and then lost 57% of its initial CS value after 3 months. The composite composed of 100% methacrylated anhydride oligomer (MAOs) showed complete degradation after 21 days. The degrees of conversion of the neat resins were 60-77%. Both the neat resins and the composites had low polymerization shrinkage ranging from 3.8 to 5.6%. (c) 2005 Wiley Periodicals, Inc.