Synthesis and polymerization of some iodine-containing monomers for biomedical applications

Abstract

Triiodophenol and iothalamic acid (5-acetamido-2,4,6-triio-N-methyl isophthalamic acid) were converted to their acrylic derivatives by esterfication with methacryloyl chloride and 2-hydroxyethyl methacrylate (HEMA), respectively. The monomers due to presence of heavy iodine atoms were expected to be radiopaque in nature. The monomers were characterized using TLC, IR, and ¹H-NMR spectroscopy. Both monomers were highly resistant to homopolymerization and copolymerization with other acrylic monomers such as methyl methacrylate (MMA) or HEMA by initiators such as 2,2'-azobis isobutyronitriie (AIBN) or benzoyl peroxide (BPO) yielding only polymers of low molecular weight. The polymers obtained were charactrized by gel permeation chromatography (GPC) and differential thermal analysis (DTA). The resistance to polymerization is presumably due to the presence of bulky iodine atoms in the monomers sterically hindering the propagation step. The decomposition temperatures of the homopolymers and copolymers were close to 300°. Copolymers of HEMA with both radiopaque monomers incorporated to the extent of 25 wt % in the feed, however, produced polymers with good radiopacity. Copolymers with HEMA were also prepared in the form of microspheres by a solvent evaporation method with the aim of using them as particles in therapeutic embolization. While the polymer based on triiodophenol was found to cause extensive blood haemolysis in in vitro tests, polymer based on iothalamic acid was found to be nonhemolytic in character suggesting that copolymers based on iothalamic acid would be suitable for implantation in the living tissue.