High performance bio‐based thermosetting resins composed of tung oil and bismaleimide

Abstract

The reaction of tung oil (TO) and 1,1 0 -(methylenedi-4,1-phenylene)bismaleimide (BMI) in 1,3-dimethyl-2-imidazolidinone (DMI) at 150 C for 4 h and subsequent precipitation gave TO/BMI prepolymer, which was cured at 200 C for 2 h gave crosslinked TO/BMI product with C¼ ¼C ratio from 1/1 to 1/4. The FE-SEM analysis revealed that all the cured products are homogeneous and no phase separation was observed. The glass transition temperature and 5% weight loss temperature of the cured TO/BMI increased with increasing BMI content. The maximal tensile strength (38.1 MPa) and modulus (2.6 GPa) were obtained for the cured products with the C¼ ¼C ratios of 1/2 and 1/3, respectively. To evaluate the reaction of TO and BMI, the model reaction products of TO and N-phenylmaleimide (PMI) in DMI were analyzed by 1 H-NMR spectroscopy. The NMR data of the reaction products of TO/PMI with the C¼ ¼C ratio 2/1, 1/1, 1/2, 1/3, and 1/4 at 150 C for 24 h revealed that Diels-Alder reaction preferentially occurred at 2/1, and that ene reaction and other reactions such as radical homo and copolymerization gradually increased with decreasing C¼ ¼C ratio of TO/PMI. V C 2010 Wiley Periodicals, Inc. J Appl Polym Sci 119: [896][897][898][899][900][901] 2011

Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides

“…XXXX, XXX, XXX−XXX which led to inevitable side reactions. 161 Our system was broadened with three different BMIs to obtain products with different properties, under milder conditions (80°C). 162 Scheme 31 illustrates the mechanism of this nonlinear DA polycondensation.…”

High-performance hybrid materials prepared by the thermo-reversible Diels–Alder polymerization of furfuryl ester-terminated butylene succinate oligomers and maleimide compounds

“…However, the influence of layered silicates on the biodegradability of the polyesters is still controversial, [11][12][13] and the environmental and toxicological implications of such nano-sized fillers are not fully understood. 15 We had already reported the crosslinking reaction of tung oil or dehydrated castor oil with BMI, 16,17 and the reaction of itaconate unit-containing PBS with methacryl-substituted polysilsesquioxane 18 as an effective reinforcement method for C¼C unsaturated group-containing bio-based resins. However, the incorporation of the rigid phenyl maleimide and silsesquioxane units causes the retardation of biodegradation, which is an important characteristic of the biobased materials.…”

Maleimide-Based Alder-Enes

“…A co-cured product of Tung oil (TO)/BMI prepolymer (cured at 200°C for 2 h) gave a bio-based high-performance cross-linked TO/BMI product (Scheme 12.24) [90] with C-C ratio from 1/1 to 1/4. To evaluate the reaction of TO and BMI, the model reaction products of TO and N-phenylmaleimide (PMI) in DMI were analyzed by 1 H-NMR spectroscopy.…”

“…14 Mechanical and Thermal Properties of Boron-Containing Alder-Ene Polymers[87] Scheme 12.24 Bio-based high-performance cross-linked TO/BMI polymer[90].…”