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Polymerization of acrylated epoxidized soybean oil with phenol furfural resins via repeated forward and retro diels–alder reactions

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Abstract

In this work, the Diels–Alder reaction between the acrylate groups of acrylated epoxidized soybean oil and the furan rings of p-tertiary butyl phenol furfural resin (TBPF) is described. The reaction was carried out at 110°C in presence of FeCl3 catalyst, and tough polymers were obtained in 1 h. Surprisingly, samples that were heated and cooled 5, 10, and 20 times to 140°C and room temperature had better mechanical properties than samples that were kept at 140°C for the same total duration. This unexpected behavior is attributed to a series of forward and retro Diels–Alder reactions between the functional groups. To prove this hypothesis, a model reaction between TBPF and n-butyl acrylate was studied. At 100°C, 1H-nuclear magnetic resonance signals of the furan ring protons disappeared, only to reappear at 140°C. Thermogravimetric analysis of the adduct showed a weight loss at 140–150°C, which was in quantitative agreement with the amount of butyl acrylate. Infrared analysis showed that furan rings were not completely consumed by extended heating at 110°C. After five heating and cooling cycles of much shorter duration at 140°C, the furan absorption in the infrared disappeared. The storage modulus of acrylated epoxidized soybean oil-TBPF samples after 20 heating cycles was 1.15 GPa. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

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