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Aromatic Polymethacrylates from Lignin-Based Feedstock: Synthesis, Thermal Properties, Life-Cycle Assessment and Toxicity

Sedrik, Rauno ; Bonjour, Olivier LU ; de Souza, Nariê Rinke Dias ; Ismagilova, Alina ; Tamsalu, Iris ; Kisand;, Veljo ; Cherubini, Francesco ; Jannasch, Patric LU orcid and Vares, Lauri (2024) In ChemSusChem
Abstract
There is currently a great need for rigid, high-performance and processable bio-based polymers and plastics as alternatives to the fossil-based materials used today. Here, we report on the straightforward synthesis and polymerization of lignin-derived methacrylate monomers based on the methyl esters of syringic, vanillic, and 4-hydroxybenzoic acid, respectively. The corresponding homopolymethacrylates exhibit high glass transition temperatures (Tgs) at 106, 128, and 197 °C, respectively. Rheological properties and thermal stability up to at least 277 °C indicate that these polymers are melt-processable. In addition, copolymers with methyl methacrylate are prepared to further vary and tune the polymer properties. An... (More)
There is currently a great need for rigid, high-performance and processable bio-based polymers and plastics as alternatives to the fossil-based materials used today. Here, we report on the straightforward synthesis and polymerization of lignin-derived methacrylate monomers based on the methyl esters of syringic, vanillic, and 4-hydroxybenzoic acid, respectively. The corresponding homopolymethacrylates exhibit high glass transition temperatures (Tgs) at 106, 128, and 197 °C, respectively. Rheological properties and thermal stability up to at least 277 °C indicate that these polymers are melt-processable. In addition, copolymers with methyl methacrylate are prepared to further vary and tune the polymer properties. An integrated ex-ante and prospective life-cycle assessment of key environmental impact parameters indicates similar or only slightly higher values compared to well-established fossil-based methyl methacrylate. Moreover, the toxicity towards human HeLa cell lines compares well with that of poly(methyl methacrylate). Hence, the potential availability of lignin-derived acids, combined with the straightforward and potentially upscalable monomer synthesis, make these rigid polymers appealing alternatives towards bio-based high-Tg thermoplastic materials with low toxicity. (Less)
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author
; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
epub
subject
in
ChemSusChem
article number
e202401239
publisher
John Wiley & Sons Inc.
ISSN
1864-564X
DOI
10.1002/cssc.202401239
language
English
LU publication?
yes
id
c547b861-8c58-4d53-bb05-b5c18f628e0b
date added to LUP
2024-03-23 09:16:00
date last changed
2024-08-29 10:21:09
@article{c547b861-8c58-4d53-bb05-b5c18f628e0b,
  abstract     = {{There is currently a great need for rigid, high-performance and processable bio-based polymers and plastics as alternatives to the fossil-based materials used today. Here, we report on the straightforward synthesis and polymerization of lignin-derived methacrylate monomers based on the methyl esters of syringic, vanillic, and 4-hydroxybenzoic acid, respectively. The corresponding homopolymethacrylates exhibit high glass transition temperatures (<i>T</i><sub>g</sub>s) at 106, 128, and 197 °C, respectively. Rheological properties and thermal stability up to at least 277 °C indicate that these polymers are melt-processable. In addition, copolymers with methyl methacrylate are prepared to further vary and tune the polymer properties. An integrated ex-ante and prospective life-cycle assessment of key environmental impact parameters indicates similar or only slightly higher values compared to well-established fossil-based methyl methacrylate. Moreover, the toxicity towards human HeLa cell lines compares well with that of poly(methyl methacrylate). Hence, the potential availability of lignin-derived acids, combined with the straightforward and potentially upscalable monomer synthesis, make these rigid polymers appealing alternatives towards bio-based high-<i>T</i><sub>g</sub> thermoplastic materials with low toxicity.}},
  author       = {{Sedrik, Rauno and Bonjour, Olivier and de Souza, Nariê Rinke Dias and Ismagilova, Alina and Tamsalu, Iris and Kisand;, Veljo and Cherubini, Francesco and Jannasch, Patric and Vares, Lauri}},
  issn         = {{1864-564X}},
  language     = {{eng}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{ChemSusChem}},
  title        = {{Aromatic Polymethacrylates from Lignin-Based Feedstock: Synthesis, Thermal Properties, Life-Cycle Assessment and Toxicity}},
  url          = {{http://dx.doi.org/10.1002/cssc.202401239}},
  doi          = {{10.1002/cssc.202401239}},
  year         = {{2024}},
}