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Lignin-Inspired Polymers with High Glass Transition Temperature and Solvent Resistance from 4-Hydroxybenzonitrile, Vanillonitrile, and Syringonitrile Methacrylates

Bonjour, Olivier LU ; Nederstedt, Hannes LU ; Arcos-Hernandez, Monica V. LU ; Laanesoo, Siim ; Vares, Lauri and Jannasch, Patric LU orcid (2021) In ACS Sustainable Chemistry & Engineering 9(50). p.16874-16880
Abstract
We here report on the synthesis and polymerization of nitrile-containing
methacrylate monomers, prepared via straightforward nitrilation of the
corresponding lignin-inspired aldehyde. The polymethacrylates reached
exceptionally high glass transition temperatures (Tg
values), i.e., 150, 164, and 238 °C for the 4-hydroxybenzonitrile,
vanillonitrile, and syringonitrile derivatives, respectively, and were
thermally stable up to above 300 °C. Copolymerizations of the nitrile
monomers with styrene and methyl methacrylate, respectively, gave
potentially melt processable materials with tunable Tg
values and enhanced solvent resistance. The use of lignin-derived
... (More)
We here report on the synthesis and polymerization of nitrile-containing
methacrylate monomers, prepared via straightforward nitrilation of the
corresponding lignin-inspired aldehyde. The polymethacrylates reached
exceptionally high glass transition temperatures (Tg
values), i.e., 150, 164, and 238 °C for the 4-hydroxybenzonitrile,
vanillonitrile, and syringonitrile derivatives, respectively, and were
thermally stable up to above 300 °C. Copolymerizations of the nitrile
monomers with styrene and methyl methacrylate, respectively, gave
potentially melt processable materials with tunable Tg
values and enhanced solvent resistance. The use of lignin-derived
nitrile-containing monomers represents an efficient strategy toward
well-defined biobased high Tg polymer materials. (Less)
Please use this url to cite or link to this publication:
author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Vanillin, Syringaldehyde, Lignocellulose, Biobased plastics, Copolymers, Acrylate polymers, Glass transition temperature
in
ACS Sustainable Chemistry & Engineering
volume
9
issue
50
pages
7 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85121048148
  • pmid:34956739
ISSN
2168-0485
DOI
10.1021/acssuschemeng.1c07048
language
English
LU publication?
yes
id
32840171-12da-43e7-b227-8e07152e6e0a
date added to LUP
2021-07-22 08:30:54
date last changed
2025-10-14 11:09:06
@article{32840171-12da-43e7-b227-8e07152e6e0a,
  abstract     = {{We here report on the synthesis and polymerization of nitrile-containing<br>
 methacrylate monomers, prepared via straightforward nitrilation of the <br>
corresponding lignin-inspired aldehyde. The polymethacrylates reached <br>
exceptionally high glass transition temperatures (<i>T</i><sub>g</sub> <br>
values), i.e., 150, 164, and 238 °C for the 4-hydroxybenzonitrile, <br>
vanillonitrile, and syringonitrile derivatives, respectively, and were <br>
thermally stable up to above 300 °C. Copolymerizations of the nitrile <br>
monomers with styrene and methyl methacrylate, respectively, gave <br>
potentially melt processable materials with tunable <i>T</i><sub>g</sub><br>
 values and enhanced solvent resistance. The use of lignin-derived <br>
nitrile-containing monomers represents an efficient strategy toward <br>
well-defined biobased high <i>T</i><sub>g</sub> polymer materials.}},
  author       = {{Bonjour, Olivier and Nederstedt, Hannes and Arcos-Hernandez, Monica V. and Laanesoo, Siim and Vares, Lauri and Jannasch, Patric}},
  issn         = {{2168-0485}},
  keywords     = {{Vanillin; Syringaldehyde; Lignocellulose; Biobased plastics; Copolymers; Acrylate polymers; Glass transition temperature}},
  language     = {{eng}},
  number       = {{50}},
  pages        = {{16874--16880}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{ACS Sustainable Chemistry & Engineering}},
  title        = {{Lignin-Inspired Polymers with High Glass Transition Temperature and Solvent Resistance from 4-Hydroxybenzonitrile, Vanillonitrile, and Syringonitrile Methacrylates}},
  url          = {{http://dx.doi.org/10.1021/acssuschemeng.1c07048}},
  doi          = {{10.1021/acssuschemeng.1c07048}},
  volume       = {{9}},
  year         = {{2021}},
}