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Issue 40, 2019
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Muconic acid esters as bio-based acrylate mimics

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Abstract

Over the course of the last century, a large number of synthetic polymers has been developed and introduced. Yet, most polymer materials are based on fossil fuels as raw materials and are associated with a considerable environmental impact. trans,trans-Muconic acid esters are interesting plant-based monomers that have not received much attention yet. The synthesis of a series of dialkyl muconates from muconic acid is described, followed by an optimization of the solution free-radical polymerization of these monomers. Unlike the claim in previous studies, dialkyl muconates can be polymerized efficiently in solution to polymers with significant molecular weights above 105 g mol−1. Polymerizations are, however, relatively slow, as can be expected for diene monomers (48 h at 120 °C). Mark–Houwink coefficients have been determined for diethyl muconate, dibutyl muconate and di(2-ethylhexyl) muconate. Furthermore, glass transition temperatures and thermal stability are assessed for the polymers, showcasing that polymuconates can serve as alternatives to polyacrylate materials. In a last step, also the reversible addition–fragmentation chain transfer (RAFT) polymerization of the muconates is investigated, showing excellent control over the molecular weight when a conventional trithiocarbonate is used to control polymerizations.

Graphical abstract: Muconic acid esters as bio-based acrylate mimics

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Publication details

The article was received on 30 Aug 2019, accepted on 23 Sep 2019 and first published on 24 Sep 2019


Article type: Paper
DOI: 10.1039/C9PY01313J
Polym. Chem., 2019,10, 5555-5563

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    Muconic acid esters as bio-based acrylate mimics

    G. Quintens, J. H. Vrijsen, P. Adriaensens, D. Vanderzande and T. Junkers, Polym. Chem., 2019, 10, 5555
    DOI: 10.1039/C9PY01313J

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