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

Aachen-Maastricht Institute of Biobased Materials (AMIBM), Faculty of Science and Engineering, Maastricht University, Brightlands Chemelot Campus, 6167 RD Geleen, The Netherlands

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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)

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Abstract

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

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MDPI and ACS Style

Noordzij, G.J.; Roy, M.; Bos, N.; Reinartz, V.; Wilsens, C.H.R.M. Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid. Polymers 2019, 11, 1654. https://doi.org/10.3390/polym11101654

AMA Style

Noordzij GJ, Roy M, Bos N, Reinartz V, Wilsens CHRM. Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid. Polymers. 2019; 11(10):1654. https://doi.org/10.3390/polym11101654

Chicago/Turabian Style

Noordzij, Geert. J., Manta Roy, Natasja Bos, Vincent Reinartz, and Carolus H.R.M. Wilsens. 2019. "Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid" Polymers 11, no. 10: 1654. https://doi.org/10.3390/polym11101654

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

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