Radiopaque Copolymers of Styryldiphenylbismuth Vinylbenzylphosphonate and Methyl Methacrylate

Abstract

Styryldiphenylbismuth (SDB) has been copolymerized with vinylbenzylphosphonate ester (VBP) and methyl methacrylate (MMA) producing highly radiopaque copolymers and terpolymers. The phosphoryl ester groups were also converted to phosphonic acids and the polymers were characterized. Thermal analysis of the co- and terpolymers yielded single glass transition temperatures in the range 60−100 °C. Poly(styryldiphenylbismuth vinylbenzylphosphonate ester) copolymer is thermally stable up to 255 °C and degrades at ca. 285 °C, producing bismuth crystallites within the partially degraded polymer matrix. Radiopacities of the polymers were compared to aluminum standards and were found to be proportional to the bismuth contents. It was found that ca. 16 mol % (or 31.6 wt %) of styryldiphenylbismuth in the terpolymer of SDB, VBP, and MMA has double the radiopacity of aluminum.

Radiation Detection: Resistivity Responses in Functional Poly(Olefin Sulfone)/Carbon Nanotube Composites

“…Bismuth (Bi) is considered to be the heaviest, non-radioactive element in the periodic table [17] and doping polymers with Bi has been shown to increase the opacity of the resulting polymers towards ionizing radiation. [18] Bi complex 4 (Scheme 3) was used for the "click-chemistry" reaction. Bismuth loadings as high as 20% (characterized by GPC, 1 H-NMR and IR) were achieved in this manner without any reduction in solubility.…”

Transparent and Photochromic Material Prepared by Copolymerization of Bismuth(III) Methacrylate

“…Owing to the high X-ray shielding ability of bismuth, poly­(BiMA- co -DMAA) could similarly shield X-rays with previously reported polymers containing bismuth. − As a preliminary experiment, we measured X-ray (Cu Kα) transmittance of the poly­(BiMA- co -DMAA) films (Figure ). As the increase of the Bi content, the transmittance of X-ray was reduced.…”

“…From this point of view, some bismuth-containing polymers have been explored. Smid et al first reported the synthesis of bismuth-containing radiopacifying polymers by copolymerization of styrylbismuthine derivatives. − However, the synthesis of these monomers requires complicated procedures, and the other properties were not described enough. Mehring et al reported preparation of bismuth-containing polymer films by copolymerization of a soluble bismuth cluster having methacryloyl groups with methyl methacrylate in N , N -dimethyl­formamide (DMF) .…”

Homo‐ and Heteroleptic Coordination Polymers and Oxido Clusters of Bismuth(III) Vinylsulfonates

“…[23, 27e] To obtain homogeneous and radiopaque polymers, triarylbismuthanes have engaged interest because of their hydrophobic charactera nd compatibility with various monomers and polymers. For example, BiPh 3 [23,28] and polymerizable 4-vinylphenylbismuthanes [29] were studied as additives for acrylate-based bone and dental cements. Materials with BiPh 3 as ar adiopacifiere xhibit lower osteolytic potentialt han comparable materials with BaSO 4 and are less cytotoxict han other clinical materials.…”