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

Laanesoo, Siim ; Bonjour, Olivier LU ; Parve, Jaan ; Parve, Omar ; Matt, Livia ; Vares, Lauri and Jannasch, Patric LU (2021) In Biomacromolecules 22(2). p.640-648
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... (More)
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. (Less)
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Biomacromolecules
volume
22
issue
2
pages
9 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85098754018
  • pmid:33307669
ISSN
1526-4602
DOI
10.1021/acs.biomac.0c01474
language
English
LU publication?
yes
id
35abf2a7-3bc3-4aeb-92fc-504cc3a9d039
date added to LUP
2020-11-27 12:08:53
date last changed
2021-03-05 03:00:31
@article{35abf2a7-3bc3-4aeb-92fc-504cc3a9d039,
  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.},
  author       = {Laanesoo, Siim and Bonjour, Olivier and Parve, Jaan and Parve, Omar and Matt, Livia and Vares, Lauri and Jannasch, Patric},
  issn         = {1526-4602},
  language     = {eng},
  number       = {2},
  pages        = {640--648},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Biomacromolecules},
  title        = {Poly(alkanoyl isosorbide methacrylate)s: from amorphous to semi-crystalline and liquid crystalline biobased materials},
  url          = {http://dx.doi.org/10.1021/acs.biomac.0c01474},
  doi          = {10.1021/acs.biomac.0c01474},
  volume       = {22},
  year         = {2021},
}