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.
Highlights
The development of both renewable monomers and polymers has received considerable interest in recent years, resulting from both declining petroleum resources and increasing environmental awareness [1,2]
In the polymerization reactions performed in this study, as shown in Scheme 1, we made use of the BP-C2 in the dicarboxylic acid form, as it can be synthesized using a green route in high yield and purity
The use of BP-C2 does not appear to limit the molecular weight build-up during polymerization as we obtain polymers with a molecular weight (Mw ) close to 20 kg/mol or higher, values common for polymers synthesized via melt-polycondensation routes
Summary
The development of both renewable monomers and polymers has received considerable interest in recent years, resulting from both declining petroleum resources and increasing environmental awareness [1,2]. An end-of-life scenario, for example biological, chemical, or mechanical recycling should be envisioned when designing polymers that are to be used in a circular economy. Known as biodegradation, could be of interest for polymers that are likely to end up in nature or other bioactive environments [3]. As is described by Swift [4], biodegradable polymers should undergo complete biodegradation in order to be considered biologically recyclable. The observance of progressive weight loss of polymers exposed to bioactive environments does not necessarily confirm their biodegradation; the polymer could erode into smaller (soluble) fragments that accumulate in nature without further degradation, as is generally the scenario for oxo-degradable polyolefin materials.
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