Synthesis and Characterization of Novel Radiopaque Polycarbonate

• Published in: Macromolecular rapid communications. Vol. 43; no. 7; pp. e2100906 - n/a
• Main Authors: Fan, You Kun, Feng, Shao Min, Liu, Xi Liang, Li, Kai Qi, Chen, Dong Liang, Xiong, Cheng Dong
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 01.04.2022
• Subjects: Benzamide; Carbonates; Catalysis; Chemical bonds; Computed tomography; Covalent bonds; Degradation; Heavy metals; Humans; Iodine; Liquid chromatography; NMR; Nuclear magnetic resonance; Opacity; Photoelectron spectroscopy; Photoelectrons; Polycarbonate; Polycarbonate resins; Polycarboxylate Cement - chemistry; Polymerization; Polymers; radiopacity; Ring opening polymerization; Room temperature; Salts; Spectroscopy; Spectrum analysis; X ray photoelectron spectroscopy; X-Ray Microtomography; iodine; polycarbonate; radiopacity; ring-opening polymerization
• ISSN: 1022-1336; 1521-3927
• DOI: 10.1002/marc.202100906

Polymeric materials implanted in the human body are usually invisible under X‐ray, and the mixing of heavy metal salts into polymeric materials by physical compounding often poses compatibility problems. A new iodine‐containing cyclic carbonate monomer, 4‐iodo‐N‐(2‐oxo‐1,3‐dioxan‐5‐yl)benzamide (IBTMC), is synthesized, which has a degradable carbonate group as its basic structural unit and iodine atoms attached to the side chain in the form of covalent bonds. The ring‐opening polymerization of IBTMC is achieved at room temperature under the catalysis of the solid superbase 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD). The structure and X‐ray developing ability of the synthesized polycarbonate are characterized by 1H‐NMR, X‐ray photoelectron spectroscopy (XPS), energy dispersive X‐ray spectroscopy (EDS), Gel Permeation Chromatography (GPC), and micro‐computed tomography (Micro‐CT). The iodine atoms remain bound to the polymer as covalent bonds after a series of reactions and exhibit a high level of X‐ray opacity. In vitro degradation experiments of the polymer prove that the polymer is degradable. A novel iodine‐containing cyclic carbonate monomer 4‐iodo‐N‐(2‐oxo‐1,3‐dioxan‐5‐yl)benzamide (IBTMC) is synthesized in two steps. The polymerization of iodine‐containing cyclic carbonates is initiated under mild conditions. Iodine atoms covalently attached to the polymer make the polymer visible under X‐rays, while the carbonate groups on the polymer backbone allow the polymer to degrade.