High Glass Transition Temperature Renewable Polymers via Biginelli Multicomponent Polymerization

Macromolecular Rapid Communications
Andreas C BoukisMichael A R Meier

Abstract

A novel and straightforward one-pot multicomponent polycondensation method was established in this work. The Biginelli reaction is a versatile multicomponent reaction of an aldehyde, a β-ketoester (acetoacetate) and urea, which can all be obtained from renewable resources, yielding diversely substituted 3,4-dihydropyrimidin-2(1H)-ones (DHMPs). In this study, renewable diacetoacetate monomers with different spacer chain lengths (C3, C6, C10, C20) were prepared via simple transesterification of renewable diols and commercial acetoacetates. The diacetoacetate monomers were then reacted with renewable dialdehydes, i.e., terephthalaldehyde and divanillin in a Biginelli type step-growth polymerization. The obtained DHMP polymers (polyDHMPs) displayed high molar masses, high glass transition temperatures (Tg) up to 203 °C and good thermal stability (Td5%) of 280 °C. The Tg of the polyDHMPs could be tuned by variation of the structure of the dialdehyde or the diacetoacetate component.

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Citations

Jul 2, 2016·Angewandte Chemie·Rosemary L KanastyDaniel G Anderson
Jul 7, 2016·Journal of the American Chemical Society·Haodong XueLei Tao
May 18, 2018·Macromolecular Rapid Communications·Haibo WuLei Tao
Sep 12, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anne-Sophie MoraSylvain Caillol
Feb 10, 2017·Beilstein Journal of Organic Chemistry·Andreas C BoukisMichael A R Meier
Oct 3, 2020·Macromolecular Rapid Communications·Guoqiang LiuLei Tao
Mar 16, 2017·Natural Product Reports·Samantha L KristufekKaren L Wooley
Sep 14, 2019·Macromolecular Rapid Communications·Eren Esen, Michael A R Meier
Dec 7, 2021·Journal of the American Chemical Society·Hongxu LiuS Thayumanavan

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