Renewable polyamides via thiol-ene ‘click’ chemistry and long-chain aliphatic segments

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Abstract

Thiol-ene ‘click’ chemistry was utilised to prepare dicarboxylic acid monomers containing two sulphur units within the backbone, which subsequently underwent polycondensation to yield a series of renewable, long-chain, fatty-acid derived linear polyamides. The linear sulphur-containing polyamides displayed number-average molecular weights of 8000–55,000 g·mol−1 and broad polydispersities biased towards higher weight fractions. Glass transition values were slightly above room temperature (31–35 °C), while melting temperatures ranged from 121 to 170 °C. This novel class of polymers exhibited an impressive property profile, most notably exceptional impact resistance, tear strength, high elasticity, very low water absorption yet high oxygen- and water vapour permeability. The presence of sulphur and the increased aliphatic segment length influenced a wide spectrum of polyamide properties due to the reduced amide linkage (and inter-chain hydrogen bonding) density and less-effective chain packing ability due to the increased atomic radii of the sulphur atoms. The data highlights the technical advantages of these polymers, while also expanding the repertoire and structure-property relationships of both long-chain- and sulphur-containing polyamides, and encouraging further development of polyamide derivatives from renewable sources.

Details

Original languageEnglish
Pages (from-to)183-192
Number of pages10
JournalPolymer
Volume153
Publication statusPublished - 26 Sep 2018
MoE publication typeA1 Journal article-refereed

    Research areas

  • Impact resistance, Polyamide, Thiol-ene ‘click’ chemistry

ID: 28561163