A renewable glucose-derived methacrylate monomer for photopolymerization: synthesis, copolymerization with MMA, and structure–property relationships

Abstract

The development of sustainable polymers from renewable resources has attracted growing attention as an alternative to petroleum-based monomers. In this study, a renewable methacrylate monomer derived from protected D-glucose (MA-IPT-GF) was synthesized and copolymerized with methyl methacrylate (MMA) via UV-induced radical photopolymerization using benzophenone as the photoinitiator. The monomer structure was confirmed by FT-IR and NMR spectroscopy, verifying the successful introduction of the methacrylate functionality into the glucofuranose framework. Photopolymerization of MA-IPT-GF with MMA produced GF–MMA copolymers, which were characterized in terms of their structural, thermal, and morphological properties. Spectroscopic analyses revealed the disappearance of the methacrylate vinyl signals after polymerization, confirming effective copolymer formation. Thermal analysis by TG/DTG and DSC demonstrated that incorporation of the glucofuranose-derived monomer slightly reduced the onset thermal stability compared with PMMA and introduced a multistep degradation profile associated with cleavage of protecting groups and subsequent backbone decomposition. A decrease in glass transition temperature was observed, which was attributed to the presence of bulky carbohydrate side groups that disrupt efficient chain packing and increase free volume within the polymer matrix. SEM analysis revealed heterogeneous surface morphology with dispersed domains within a PMMA-rich matrix, while EDX analysis confirmed the presence of chlorine-containing protecting groups in the copolymer structure. XRD results further indicated that the copolymer maintains a predominantly amorphous structure with increased structural disorder due to the incorporation of the sugar-based monomer. Overall, the results demonstrate that glucose-derived methacrylate monomers can be incorporated into MMA-based copolymers through photopolymerization, providing renewable photocurable polymer systems.