Synthesis and Photo-Polymerization of Bio-Based Furanic Compounds Functionalized by 2-Hydroxypropyl Methacrylate Group(s)

Bio-based compounds (FmHPM and FdHPM) with a furan backbone and photo-polymerizable 2-hydroxypropyl methacrylate (HPM) group(s) were synthesized from carbohydrate-derived furanyl alcohols (furan-2-methanol and furan-2,5-dimethanol) and their photo-polymerizing behaviors and mechanical properties after photo-polymerization were investigated. Half time values (t(1/2)) of bio-based FmHPM and FdHPM were 10.4 s and 3.0 s and their shrinkage ratios were 3.0 and 6.1% during photo-polymerization, respectively. Tensile-shear strength of glass and polycarbonate joints bonded by bio-based furanic compounds appeared in range of 0.2-0.6 MPa and pencil hardness of film coated by bio-based furanic compounds after photo-polymerization showed 2H-3H. Newly synthesized bio-based furanic compounds allowed the feasibility to alternate petroleum-based Bis-GMA/TEGDMA, photo-polymerizable composition widely utilized in a variety of applications. (C) 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 127: 2483-2489, 2013