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

Geert. J. Noordzij, Manta Roy, Natasja Bos, Vincent Reinartz, Carolus H. R. M. Wilsens*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Web of Science)

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 languageEnglish
Article number1654
Number of pages14
JournalPolymers
Volume11
Issue number10
DOIs
Publication statusPublished - 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

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