Synthesis and photo‐polymerization of bio‐based furanic compounds functionalized by 2‐hydroxypropyl methacrylate group(s)

Abstract

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.

A chemical platform approach on cardanol oil: from the synthesis of building blocks to polymer synthesis

“…Literature reports interesting studies on the replacement of MDGEBA prepolymer for VE networks. Thus, the use of isosorbide diglycidyl ether (Lukaszczyk et al, 2012;Sadler et al, 2013;Chrysanthos et al, 2011) or furfuryl derivatives (Jeong et al, 2013) was reported, but the properties of obtained materials do not meet the needed thermal properties for targeted applications. The synthesis of VE networks from vegetable oils is also reported in literature.…”

Synthesis and characterization of novel vinylester prepolymers from cardanol

“…Among the available literature on the synthesis of VE resins from renewable resources, few refer to aromatic monomers, and particularly cardanol. Indeed, some publications deal with prepolymers from glucose derivatives such as isosorbide , from wood derivatives such as furan , and extracted from plants such as phloroglucinol and vanillin . However, several publications concern acrylated vegetable oils used as reactive diluents of VE resins , or used as VE prepolymers .…”

Photo‐curing behaviors of bio‐based isosorbide dimethacrylate by irradiation of light‐emitting diodes and the physical properties of its photo‐cured materials

“…The prepared assemblies were photo‐cured by irradiation using LED lamp. Based on a reported method, additional plates (2.54 × 5.08 cm 2 ) with the same thickness were attached on both ends of the specimens for grip. The tensile‐shear strengths of the joints bonded by the photo‐curing procedure were measured using universal testing machine (UTM) (5967, INSTRON, USA), and the loading rate was 1.27 cm/min.…”

“…Therefore, photo‐curable materials should be derived from petroleum‐independent and nontoxic chemicals instead of BPA. However, only a few examples of bio‐based photo‐curable materials bearing a rigid backbone have been reported …”