Affiliation:
1. Key Laboratory of High Performance Plastics, Ministry of Education, College of Chemistry, Jilin University, Changchun, People’s Republic of China
2. Endodontics Department of Stomatological Hospital, Jilin University, Changchun, China
Abstract
Bisphenol A (BPA), as an endocrine disruptor derived from petroleum-based chemicals, has been prohibited by several regulatory agencies for use in a wide variety of consumer products. For the sake of reducing human exposure to BPA derivatives and in the context of sustainability, it is far-reaching to develop high-performance and low-toxic materials from bountiful biomass sources. The objective of this work was to synthesize 2 bio-based dimethacrylate monomers, 2,2′-dially-4,4′-dimethoxy-5,5′-diglycerolate acrylatediphenylmethane (BEF-EA) and 2,2′-dially-4,4′-dimethoxy-5,5′-diglycerolate methacrylatediphenylmethane (BEF-GMA), using eugenol as the raw material. The estrogenic activity of bio-based bisphenol 2,2′-dially-4,4′-dimethoxy-5,5′-dihydroxydiphenylmethane (BEF) was evaluated and compared with estrogen and commercial bisphenols. After photopolymerization of the di(meth)acrylates diluted with tri(ethyleneglycol) dimethacrylate (TEGDMA), bio-based visible light-curing materials were prepared, and their properties were systematically investigated. Notably, di(meth)acrylates BEF-GMA and BEF-EA derived from these nonestrogenic bio-based phenols exhibited improved biocompatibility and low viscosity (down to 220–280 Pa.s). BEF-GMA and BEF-EA resin matrix exhibits lower volumetric polymerization shrinkage (about 8.5%), high photopolymerization reactivity (>50% in 60 s), and mechanical properties (fracture energy >5.5 N mm; flexural strength of 87–91 MPa, etc), which were comparable or superior to commercial Bis-GMA. The respective bio-based composites still exhibit adequate properties. Therefore, introducing eugenol-based visible light-curable dimethacrylate monomers into dental materials is a potential strategy to establish green sustainability and biocompatible dental materials without BPA.
Funder
State Grid Corporation of China
National Natural Science Foundation of China
Cited by
8 articles.
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