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Synthesis of Homo- and Copolyesters Using an AB-Type Aromatic Monomer Based on Homovanillic Acid

Nguyen, Tam T. LU ; Olsson, Emma ; Mankar, Smita V. LU ; Warlin, Niklas LU ; Valsange, Nitin G. LU ; Engqvist, Jonas LU ; Rehnberg, Nicola LU orcid ; Jannasch, Patric LU orcid and Zhang, Baozhong LU (2024) In Macromolecules 57(19). p.9289-9301
Abstract
There is currently intensive research ongoing with the aim to utilize
various lignin-derived molecules to produce aromatic monomers and
polymers. In the present work, homovanillic acid (HVA), derived from
lignin, was used to prepare sustainable polyesters for the first time.
An AB-type monomer with an alcohol group and a carboxylate ester group
was conveniently synthesized by using HVA and ethylene carbonate. The
monomer was employed in bulk polycondensation to yield the corresponding
homopolyester. The polymerization temperature, catalyst, and time were
optimized, and it was found that the addition of a small quantity of a
dicarboxylate monomer facilitated a stoichiometric balance throughout... (More)
There is currently intensive research ongoing with the aim to utilize
various lignin-derived molecules to produce aromatic monomers and
polymers. In the present work, homovanillic acid (HVA), derived from
lignin, was used to prepare sustainable polyesters for the first time.
An AB-type monomer with an alcohol group and a carboxylate ester group
was conveniently synthesized by using HVA and ethylene carbonate. The
monomer was employed in bulk polycondensation to yield the corresponding
homopolyester. The polymerization temperature, catalyst, and time were
optimized, and it was found that the addition of a small quantity of a
dicarboxylate monomer facilitated a stoichiometric balance throughout
the homopolycondensation of the AB-type monomer, and thus significantly
enhanced the molecular weight of the polyester (Mn = 36 kg mol–1, [η] ∼ 1.1 dL g–1).
Copolymerization of the HVA-based monomer with another lignin-based AB
monomer, methyl 4-(2-hydroxyethoxy) benzoate, produced a series of
copolyesters with high yields and moderate molecular weights (Mn = 9.5–11 kg mol–1, [η] ∼ 0.5 dL g–1). The resulting copolyesters showed a reasonably high thermal stability (Td,5% > 318 °C) and tunable thermal properties, e.g., Tg = 44–72 °C and Tm
= 154–200 °C, depending on the monomeric composition. Consequently, the
findings of this work demonstrated the great potential of HVA in the
development of new biobased aromatic (co)polyesters with modulated
crystallinity. (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
in
Macromolecules
volume
57
issue
19
pages
9289 - 9301
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85205753112
ISSN
0024-9297
DOI
10.1021/acs.macromol.4c00877
language
English
LU publication?
yes
id
2cf52dd5-902f-47f4-a89f-b2081eb98bc2
date added to LUP
2024-04-17 14:44:17
date last changed
2024-12-08 04:06:36
@article{2cf52dd5-902f-47f4-a89f-b2081eb98bc2,
  abstract     = {{There is currently intensive research ongoing with the aim to utilize <br>
various lignin-derived molecules to produce  aromatic monomers and <br>
polymers. In the present work, homovanillic acid (HVA), derived from <br>
lignin, was used to prepare sustainable polyesters for the first time. <br>
An AB-type monomer with an alcohol group and a carboxylate ester group <br>
was conveniently synthesized by using HVA and ethylene carbonate. The <br>
monomer was employed in bulk polycondensation to yield the corresponding<br>
  homopolyester. The polymerization temperature, catalyst, and time were<br>
 optimized, and it was found that the addition of a small quantity of a <br>
dicarboxylate monomer facilitated a stoichiometric balance throughout <br>
the homopolycondensation of the AB-type monomer, and thus significantly <br>
enhanced the molecular weight of the polyester (<i>M</i><sub>n</sub> = 36 kg mol<sup>–1</sup>, [η] ∼ 1.1 dL g<sup>–1</sup>).<br>
 Copolymerization of the HVA-based monomer with another lignin-based AB <br>
monomer, methyl 4-(2-hydroxyethoxy) benzoate, produced a series of <br>
copolyesters with high yields and moderate molecular weights (<i>M</i><sub>n</sub> = 9.5–11 kg mol<sup>–1</sup>, [η] ∼ 0.5 dL g<sup>–1</sup>). The resulting copolyesters showed a reasonably high thermal stability (<i>T</i><sub>d,5%</sub> &gt; 318 °C) and tunable thermal properties, e.g., <i>T</i><sub>g</sub> = 44–72 °C and <i>T</i><sub>m</sub><br>
 = 154–200 °C, depending on the monomeric composition. Consequently, the<br>
 findings of this work demonstrated the great potential of HVA in the <br>
development of new biobased aromatic (co)polyesters with modulated <br>
crystallinity.}},
  author       = {{Nguyen, Tam T. and Olsson, Emma and Mankar, Smita V. and Warlin, Niklas and Valsange, Nitin G. and Engqvist, Jonas and Rehnberg, Nicola and Jannasch, Patric and Zhang, Baozhong}},
  issn         = {{0024-9297}},
  language     = {{eng}},
  number       = {{19}},
  pages        = {{9289--9301}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Macromolecules}},
  title        = {{Synthesis of Homo- and Copolyesters Using an AB-Type Aromatic Monomer Based on Homovanillic Acid}},
  url          = {{http://dx.doi.org/10.1021/acs.macromol.4c00877}},
  doi          = {{10.1021/acs.macromol.4c00877}},
  volume       = {{57}},
  year         = {{2024}},
}