Poly(alkanoyl isosorbide methacrylate)s: from amorphous to semi-crystalline and liquid crystalline biobased materials

Siim Laanesoo, Olivier Bonjour, Jaan Parve, Omar Parve, Livia Matt, Lauri Vares, Patric Jannasch

Research output: Contribution to journalArticlepeer-review

5 Citations (SciVal)

Abstract

We have prepared a series of twelve D-isosorbide-2-alkanoate-5-methacrylate monomers as single regioisomers with different pendant linear C2 to C20 alkanoyl chains by using biocatalytic and chemical acylations. By conventional radical polymerization, these monomers afforded high-molecular weight biobased poly(alkanoyl isosorbide methacrylate)s (PAIMAs). Samples with C2-C12 alkanoyl chains were amorphous with glass transition temperatures from 107 to 54 °C, while C14-C20 chains gave semi-crystalline materials with melting points up to 59 °C. Moreover, PAIMAs with C13-C20 chains formed liquid crystalline mesophases with transition temperatures up to 93 °C. The mesophases were studied by polarized optical microscopy, and rheology showed stepwise changes of the viscosity at the transition temperature. Unexpectedly, a PAIMA prepared from a regioisomeric monomer (C18) showed semi-crystallinity but no liquid crystallinity. Consequently, the properties of the PAIMAs were readily tunable by controlling the phase structure and transitions through the alkanoyl chain length and the regiochemistry to form fully amorphous, semi-crystalline or semi-/liquid crystalline materials.
Original languageEnglish
Pages (from-to)640-648
Number of pages9
JournalBiomacromolecules
Volume22
Issue number2
DOIs
Publication statusPublished - 2021

Subject classification (UKÄ)

  • Polymer Technologies
  • Polymer Chemistry
  • Organic Chemistry
  • Physical Chemistry

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