Renewable polyamides via thiol-ene ‘click’ chemistry and long-chain aliphatic segments
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 di...
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Published in | Polymer (Guilford) Vol. 153; pp. 183 - 192 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Kidlington
Elsevier Ltd
26.09.2018
Elsevier BV |
Subjects | |
Online Access | Get full text |
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Summary: | 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.
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•Renewable sulphur-containing polyamides were synthesised via ‘click’ chemistry.•Polyamides displayed exceptional impact- and tear resistance, low water absorption.•Polyamides also displayed high oxygen- and water permeability.•Properties influenced by the presence of sulphur and long repeating-unit length. |
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ISSN: | 0032-3861 1873-2291 |
DOI: | 10.1016/j.polymer.2018.08.033 |