Jump to main content
Jump to site search

Issue 52, 2017
Previous Article Next Article

Aromatic poly(ether ester)s derived from a naturally occurring building block nipagin and linear aliphatic α,ω-diols

Author affiliations

Abstract

Nipagin, the methyl ester of p-hydroxybenzoic acid, which is present naturally in campanulaceae and ericaceous plants, was used to prepare poly(ether ester)s. In this study, two nipagin-based aromatic dimethyl esters were synthesized via one-step simple nucleophilic substitutions with methyl chloroacetate and 1,4-dibromobutane, respectively. Subsequently, two series of poly(ether ester)s, PN1-ωs and PN2-ωs, were synthesized using linear aliphatic α,ω-diols (n = 2, 3, 4, 6, 10, 12) after optimizing the reaction conditions, like feed ratio, reaction catalyst, time and temperature. The synthesized poly(ether ester)s exhibit weight-average molecular weights (Mws) in the range of 9300–32 100 g mol−1, together with dispersity (D) values between 1.5 and 1.8. 1H NMR, 13C NMR and FTIR spectroscopy were used to characterize their chemical structures. The thermal properties were studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The results show that the nipagin-based poly(ether ester)s exhibit excellent thermal stability with the initial decomposition temperature above 350 °C and a two-step degradation mechanism. Glass transition (Tg), melting and crystallization temperatures (Tm, Tc), and the corresponding melting and crystallization enthalpies (ΔHm, ΔHc) are closely related to the lengths of the α,ω-diols. The Tg values show a decreasing trend with a gradual increase in α,ω-diol length in both PN1-ωs and PN2-ωs. The crystallization behaviors were also studied by isothermal crystallization and wide-angle X-ray diffraction (WAXD). The crystallizability proves to be enhanced with a gradual increase in α,ω-diol length in each series. The mechanical properties were studied using tensile assays and dynamic mechanical analysis (DMA), which show that the nipagin-based poly(ether ester)s feature excellent mechanical properties with elastic modulus and tensile strength values reaching 600–800 MPa and 10–35 MPa, respectively. Finally, the nipagin-based poly(ether ester)s feature excellent comprehensive performance and the renewable nipagin will broaden the thermoplastic spectrum and have practical applications in the field of polymeric materials.

Graphical abstract: Aromatic poly(ether ester)s derived from a naturally occurring building block nipagin and linear aliphatic α,ω-diols

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Feb 2017, accepted on 23 Jun 2017 and first published on 29 Jun 2017


Article type: Paper
DOI: 10.1039/C7RA01810J
RSC Adv., 2017,7, 32989-33000
  • Open access: Creative Commons BY license
  •   Request permissions

    Aromatic poly(ether ester)s derived from a naturally occurring building block nipagin and linear aliphatic α,ω-diols

    K. Hu, D. Zhao, G. Wu and J. Ma, RSC Adv., 2017, 7, 32989
    DOI: 10.1039/C7RA01810J

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements