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Open AccessArticle

Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid

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Chemelot InSciTe, Urmonderbaan 20F, NL-6167 RD Geleen, The Netherlands
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Aachen-Maastricht Institute of Biobased Materials (AMIBM), Faculty of Science and Engineering, Maastricht University, Brightlands Chemelot Campus, 6167 RD Geleen, The Netherlands
*
Author to whom correspondence should be addressed.
Polymers 2019, 11(10), 1654; https://doi.org/10.3390/polym11101654
Received: 31 July 2019 / Revised: 26 September 2019 / Accepted: 4 October 2019 / Published: 11 October 2019
(This article belongs to the Collection Sustainable Polymeric Materials from Renewable Resources)
In this work, we report on the synthesis of a series of polyesters based on 1,6-hexanediol, sebacic acid, and N,N’-dimethylene-bis(pyrrolidone-4-carboxylic acid) (BP-C2), of which the latter is derived from renewable itaconic acid and 1,2-ethanediamine. Copolymers with a varying amount of BP-C2 as dicarboxylic acid are synthesized using a melt-polycondensation reaction with the aim of controlling the hydrolysis rate of the polymers in water or under bioactive conditions. We demonstrate that the introduction of BP-C2 in the polymer backbone does not limit the molecular weight build-up, as polymers with a weight average molecular weight close to 20 kg/mol and higher are obtained. Additionally, as the BP-C2 moiety is excluded from the crystal structure of poly(hexamethylene sebacate), the increase in BP-C2 concentration effectively results in a suppression in both melting temperature and crystallinity of the polymers. Overall, we demonstrate that the BP-C2 moiety enhances the polymer’s affinity to water, effectively improving the water uptake and rate of hydrolysis, both in demineralized water and in the presence of a protease from Bacillus licheniformis. View Full-Text
Keywords: bis-pyrrolidone dicarboxylic acid; aliphatic polyester; hydrolysis; enzymatic depolymerization; itaconic acid; polycondensation bis-pyrrolidone dicarboxylic acid; aliphatic polyester; hydrolysis; enzymatic depolymerization; itaconic acid; polycondensation
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MDPI and ACS Style

Noordzij, G.J.; Roy, M.; Bos, N.; Reinartz, V.; Wilsens, C.H. Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid. Polymers 2019, 11, 1654.

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