Materials 2010, 3(1), 369-385; doi:10.3390/ma3010369
Article

Synthesis and Properties of Trehalose-Based Flexible Polymers Prepared from Difurfurylidene Trehalose and Maleimide- Terminated Oligo(dimethylsiloxane) by Diels-Alder Reactions

Received: 13 November 2009; in revised form: 16 December 2009 / Accepted: 8 January 2010 / Published: 12 January 2010
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Difurfurylidene trehalose (DFTreh) was synthesized from trehalose and furfural by an acetalization reaction. Maleimide-terminated dimethylsiloxane oligomers (DMS-BMI) were synthesized from amine-terminated dimethylsiloxane oligomers by condensation with maleic anhydride. Three types of DMS-BMI with different length were prepared. Trehalose-based polymers were synthesized by Diels-Alder reaction of DFTreh and DMS-BMI. The reaction proceeded at 40~70 °C to produce a polymer with a maximum weight average molecular weight of ~19,000. The thermal degradation temperature increased with the increase of the length of the oligo(dimethylsiloxane) units. The differential scanning calorimetry (DSC) measurements revealed the glass transition temperature (Tg) of the polymer at -130~-120 °C, and no distinct Tg not observed above room temperature in the DSC measurement. The polymer products are not liquid at room temperature, and solid films can be obtained by casting from solution, implying a phase-separated structure made up of soft and hard segments. The phase-separated structure was confirmed by transmission electron microscope (TEM) study. The DSC curve of the polymer showed a broad endothermic peak at 110~160 °C, suggesting that a retro-Diels-Alder reaction occurred. When a N,N-dimethylformamide solution of the polymer was kept at 100 °C and the resulting solution was analyzed by gel permeation chromatography (GPC), the molecular weight decreased and monomers appeared.
Keywords: trehalose; poly(dimethylsiloxane); Diels-Alder reaction; furfural; renewable resources
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MDPI and ACS Style

Teramoto, N.; Niwa, M.; Shibata, M. Synthesis and Properties of Trehalose-Based Flexible Polymers Prepared from Difurfurylidene Trehalose and Maleimide- Terminated Oligo(dimethylsiloxane) by Diels-Alder Reactions. Materials 2010, 3, 369-385.

AMA Style

Teramoto N, Niwa M, Shibata M. Synthesis and Properties of Trehalose-Based Flexible Polymers Prepared from Difurfurylidene Trehalose and Maleimide- Terminated Oligo(dimethylsiloxane) by Diels-Alder Reactions. Materials. 2010; 3(1):369-385.

Chicago/Turabian Style

Teramoto, Naozumi; Niwa, Masashi; Shibata, Mitsuhiro. 2010. "Synthesis and Properties of Trehalose-Based Flexible Polymers Prepared from Difurfurylidene Trehalose and Maleimide- Terminated Oligo(dimethylsiloxane) by Diels-Alder Reactions." Materials 3, no. 1: 369-385.

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