Bio-based Non-estrogenic Dimethacrylate Dental Composite from Cloves

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.