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Combining isosorbide and lignin-related benzoic acids for high-Tg polymethacrylates

Laanesoo, Siim ; Bonjour, Olivier LU ; Sedrik, Rauno ; Tamsalu, Iris ; Jannasch, Patric LU orcid and Vares, Lauri (2024) In European Polymer Journal 202.
Abstract
The insertion of rigid aliphatic or aromatic building blocks in polymer structures is an efficient synthetic strategy towards high-Tg polymer materials. In the present work, we have functionalized isosorbide 5-methacrylate with various aromatic lignin-inspired esters to yield a series of isosorbide-2-aryl carboxylate-5-methacrylate monomers (ArIMAs) as single regioisomers. The selection of phenyl carboxylate side groups included benzoate, p-cyanobenzoate, meta/para-methoxybenzoates, and different vanillic acid esters. This afforded a range of seven bio-based monomers with different size, polarity, and substitutions. Polymerizations were carried out by conventional free radical initiation to obtain the corresponding... (More)
The insertion of rigid aliphatic or aromatic building blocks in polymer structures is an efficient synthetic strategy towards high-Tg polymer materials. In the present work, we have functionalized isosorbide 5-methacrylate with various aromatic lignin-inspired esters to yield a series of isosorbide-2-aryl carboxylate-5-methacrylate monomers (ArIMAs) as single regioisomers. The selection of phenyl carboxylate side groups included benzoate, p-cyanobenzoate, meta/para-methoxybenzoates, and different vanillic acid esters. This afforded a range of seven bio-based monomers with different size, polarity, and substitutions. Polymerizations were carried out by conventional free radical initiation to obtain the corresponding high molecular-weight poly(aryl carboxylate isosorbide methacrylate)s (PArIMAs). The polymerizations were evaluated in different solvents, including toluene, EtOAc, γ-valerolactone, 2-MeTHF, and DMSO to identify the most suitable conditions. The polymers exhibited high glass transition temperatures (Tgs) in a broad range, from 80 to 168 °C, and were thermally stable up to 268 °C. Furthermore, dynamic rheology experiments indicated that the polymers were sufficiently stable for melt processing. The availability of the building blocks combined with the high stability of the polymers make these materials attractive for use as high-performance plastics and coatings.
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
isosorbide, lignin, polymethacrylate, bio-based plastic, high Tg
in
European Polymer Journal
volume
202
article number
112595
pages
8 pages
publisher
Elsevier
external identifiers
  • scopus:85178222757
ISSN
0014-3057
DOI
10.1016/j.eurpolymj.2023.112595
language
English
LU publication?
yes
id
102cba7a-7ec4-494b-93bd-a38e9c73ea1f
date added to LUP
2023-09-06 15:49:23
date last changed
2023-12-11 04:01:28
@article{102cba7a-7ec4-494b-93bd-a38e9c73ea1f,
  abstract     = {{The insertion of rigid aliphatic or aromatic building blocks in polymer structures is an efficient synthetic strategy towards high-<i>T</i><sub>g</sub> polymer materials. In the present work, we have functionalized isosorbide 5-methacrylate with various aromatic lignin-inspired esters to yield a series of isosorbide-2-aryl carboxylate-5-methacrylate monomers (ArIMAs) as single regioisomers. The selection of phenyl carboxylate side groups included benzoate, <i>p</i>-cyanobenzoate, meta/para-methoxybenzoates, and different vanillic acid esters. This afforded a range of seven bio-based monomers with different size, polarity, and substitutions. Polymerizations were carried out by conventional free radical initiation to obtain the corresponding high molecular-weight poly(aryl carboxylate isosorbide methacrylate)s (PArIMAs). The polymerizations were evaluated in different solvents, including toluene, EtOAc, γ-valerolactone, 2-MeTHF, and DMSO to identify the most suitable conditions. The polymers exhibited high glass transition temperatures (<i>T</i><sub>g</sub>s) in a broad range, from 80 to 168 °C, and were thermally stable up to 268 °C. Furthermore, dynamic rheology experiments indicated that the polymers were sufficiently stable for melt processing. The availability of the building blocks combined with the high stability of the polymers make these materials attractive for use as high-performance plastics and coatings.<br/>}},
  author       = {{Laanesoo, Siim and Bonjour, Olivier and Sedrik, Rauno and Tamsalu, Iris and Jannasch, Patric and Vares, Lauri}},
  issn         = {{0014-3057}},
  keywords     = {{isosorbide; lignin; polymethacrylate; bio-based plastic; high Tg}},
  language     = {{eng}},
  publisher    = {{Elsevier}},
  series       = {{European Polymer Journal}},
  title        = {{Combining isosorbide and lignin-related benzoic acids for high-<i>T</i><sub>g</sub> polymethacrylates}},
  url          = {{http://dx.doi.org/10.1016/j.eurpolymj.2023.112595}},
  doi          = {{10.1016/j.eurpolymj.2023.112595}},
  volume       = {{202}},
  year         = {{2024}},
}