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-C-2), of which the latter is derived from renewable itaconic acid and 1,2-ethanediamine. Copolymers with a varying amount of BP-C-2 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-C-2 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-C-2 moiety is excluded from the crystal structure of poly(hexamethylene sebacate), the increase in BP-C-2 concentration effectively results in a suppression in both melting temperature and crystallinity of the polymers. Overall, we demonstrate that the BP-C-2 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.
Original language | English |
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Article number | 1654 |
Number of pages | 14 |
Journal | Polymers |
Volume | 11 |
Issue number | 10 |
DOIs | |
Publication status | Published - Oct 2019 |
Keywords
- bis-pyrrolidone dicarboxylic acid
- aliphatic polyester
- hydrolysis
- enzymatic depolymerization
- itaconic acid
- polycondensation
- VERSATILE BUILDING-BLOCK
- ITACONIC ACID
- ENZYMATIC-HYDROLYSIS
- DEGRADATION
- POLYESTERS
- BIODEGRADATION
- POLY(L-LACTIDE)
- BIOPOLYAMIDES
- PERFORMANCE
- POLYAMIDES