Polyurethanes with radiopaque properties

Abstract

An aliphatic, commercially available, medical grade polyurethane, Tecoflex 80 A was made radiopaque by coupling a 5-iodine-containing molecule, N-(2,6- diiodocarboxyphenyl)-3,4,5-triiodo benzamide (DCPTB) onto the polymer backbone. DCPTB was synthesized by coupling 4-amino-3,5-diiodobenzoic acid and 3,4,5-triiodobenzoic acid using dicyclohexyl carbodiimide. Radiopaque polyurethane thus obtained was characterized by IR, TGA, DSC and X-radiography. By optimizing the reaction conditions, it was possible to incorporate about 8% iodine in the polymer (wt/wt) to achieve radiopacity almost equivalent to that of a 2 mm thick aluminium wedge. However, the products differed from the starting polymer in thermal characteristics. The starting polymer showed two endothermic transitions, the first one due to glass transition of the soft segment and the second one due to disruption of the hard segments. After modification, the second transition shifted to a lower temperature, while the first transition remained unaltered. Also, the modified polymers showed reduced thermal stability compared to the starting polymer. These observations could be explained on the basis of the reduced extent of intermolecular hydrogen bonding among the hard segments of the end product. Radiopaque polyurethanes are expected to have significant advantage over their non-radiopaque counterparts in many medical and related applications.