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Home  >  Journal list  >  Polymer Journal  >  Vol.43  No.5 (2011)  >  pp.455-463

Polymer Journal
<<Previous article Vol.43  No.5 (2011)   pp.455 - 463 Next article>>

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

Mitsuhiro Shibata1, Naozumi Teramoto1, Takayuki Akiba1 and Megumi Ogihara1
1Department of Life and Environmental Sciences, Faculty of Engineering, Chiba Institute of Technology, Narashino, Japan

A furfuryl ester-terminated butylene succinate oligomer (FBSO) with Mn 1800 and Mw 2800 was synthesized by the condensation of furfuryl alcohol with a carboxyl-terminated butylene succinate oligomer. The reaction of FBSO and 1,1′-(methylenedi-4,1-phenylene)bismaleimide (BMI) in chloroform at 60°C for 48h yielded an exo-rich Diels–Alder (DA) adduct ((P(FBSO-BMI)) with Mn 9000 and Mw 15500. The gel permeation chromatography analysis of the products of heating a reaction mixture of P(FBSO-BMI) in dimethylformamide (DMF) at 120°C for 1h revealed that FBSO and BMI are quantitatively recovered by the retro DA reaction. Maleimide/phenyl-substituted oligomeric silsesquioxane (MPOSS) was synthesized by the reaction of maleimidemethyl 3-(triethoxysilyl)propylcarbamate and triethoxyphenylsilane in the presence of hydrochloric acid. The DA reaction of FBSO and MPOSS in DMF at 60°C for 48h gave a partially crosslinked hybrid composite insoluble in general organic solvents. When the hybrid composite was heated in DMF at 140°C, the retro DA reaction proceeded smoothly. The hybrid film prepared by casting a DMF solution of FBSO and MPOSS and subsequently heating at 60°C for 48h had a much higher flexural strength than FBSO did.


Keyword:
bio-based polymer; Diels–Alder reaction; furan; maleimide; organic–inorganic hybrid; poly(butylene succinate); silsesquioxane

Received: November 22, 2010 , Revised: December 21, 2010
Accepted: January 13, 2011 , Published online: March 02, 2011
© 2011 The Society of Polymer Science, Japan

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