Synthesis and Characterization of Furan-Based Methacrylate Oligomers Containing the Imine Functional Group for Stereolithography

Abstract

Herein, a furan-based methacrylate oligomer (FBMO) featuring imine functional groups was synthesized for application in stereolithography. The preparation involved the imination reaction of 5-hydroxymethylfurfural (5-HMF) and amino ethanol. Utilizing 5-HMF as a sustainable building block for furan-based polymers, FBMO was formulated and subsequently integrated into photosensitive resin formulations along with methacrylate-containing diluents, such as PEGDMA and TEGDMA. The synthesized furan-based methacrylate oligomers underwent comprehensive characterization using FTIR, 1H NMR spectroscopy, and size exclusion chromatography. The impact of methacrylate-containing diluents on various properties of the formulated resins and the resulting 3D-printed specimens was systematically evaluated. This assessment included an analysis of rheological behavior, printing fidelity, mechanical properties, thermal stability, surface morphology, and cytotoxicity. By adjusting the ratios of FBMO to methacrylate-containing diluents within the range of 50:50 to 90:10, the viscosity of the resulting resins was controlled to fall within 0.04 to 0.28 Pa s at a shear rate of 10 s-1. The 3D-printed specimens exhibited precise conformity to the computer-aided design (CAD) model and demonstrated compressive moduli ranging from 0.53 ± 0.04 to 144 ± 6.70 MPa, dependent on the resin formulation and internal structure. Furthermore, cytotoxicity assessments revealed that the 3D-printed specimens were noncytotoxic to porcine chondrocytes. In conclusion, we introduce a new strategy to prepare the furan-based methacrylate oligomer (FBMO) and 3D-printed specimens with adjustable properties using stereolithography, which can be further utilized for appropriate applications. © 2024 The Authors. Published by American Chemical Society.