Microwave-assisted synthesis of isosorbide-derived diols for the preparation of thermally stable thermoplastic polyurethane

Designed Monomers and Polymers
Nejib KasmiAlessandra Lorenzetti

Abstract

In order to prepare thermally stable isosorbide-derived thermoplastic polyurethane, the synthesis of two new chiral exo-exo configured diols, prepared from isosorbide, and two types of diphenols (bisphenol A and thiodiphenol) was described. The synthesis conditions were optimized under conventional heating and microwave irradiations. To prove their suitability in polymerization, these monomers were successfully polymerized using 4,4'-diphenylmethane diisocyanate (MDI) and hexamethylene diisocyanate (HDI). Both monomers and polymers have been studied by NMR, FT-IR, TGA, DSC; intrinsic viscosity of polymers has also been determined. The results showed the effectiveness of the synthetic strategy proposed; moreover, a dramatic reduction of the reaction time and an important improvement of the monomers yield using microwave irradiation have been demonstrated. The monomers, as well as the polymers, showed excellent thermal stability both in air and nitrogen. It was also shown that the introduction of sulphur in the polyurethane backbone was effective in delaying the onset of degradation as well as the degradation rate.

References

Jan 4, 2012·ChemSusChem·Marcus Rose, Regina Palkovits
Dec 12, 2012·Angewandte Chemie·C Oliver KappeDoris Dallinger
Oct 23, 2016·Designed Monomers and Polymers·Asma SaadaouiMongia Said Zina

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Citations

Apr 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Se-Ra ShinDai-Soo Lee

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Methods Mentioned

BETA
differential scanning calorimetry
NMR

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