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Toward Fully Biobased Polyesters with Spiroacetal Units: Synthesis and Enzymatic Depolymerization

Mankar, Smita V. LU ; Linares-Pastén, Javier A. LU orcid ; Nguyen, Tam T. LU ; Wahlberg, Jan ; Warlin, Niklas LU ; Valsange, Nitin G. LU ; Rehnberg, Nicola LU orcid ; Lundmark, Stefan ; Jannasch, Patric LU orcid and Zhang, Baozhong LU (2026) In Macromolecular Materials and Engineering 311(5).
Abstract
There has been active research in the development of new rigid biobased
aromatic dicarboxylate monomers that can replace the widely used
fossil-based dimethyl terephthalate in polyester production. In this
work, a new biobased dicarboxylate monomer with a spiroacetal unit was
synthesized from biobased vanillin and pentaerythritol, which aims to
partially or completely replace the fossil-based dimethyl terephthalate
monomer in the production of polyesters. Polyesterification of the new
spirocetal diester monomer, 1,6-hexanediol, in the presence or absence
of dimethyl terephthalate, yielded a series of copolyesters with a
tunable monomer composition and properties. The incorporated rigid
... (More)
There has been active research in the development of new rigid biobased
aromatic dicarboxylate monomers that can replace the widely used
fossil-based dimethyl terephthalate in polyester production. In this
work, a new biobased dicarboxylate monomer with a spiroacetal unit was
synthesized from biobased vanillin and pentaerythritol, which aims to
partially or completely replace the fossil-based dimethyl terephthalate
monomer in the production of polyesters. Polyesterification of the new
spirocetal diester monomer, 1,6-hexanediol, in the presence or absence
of dimethyl terephthalate, yielded a series of copolyesters with a
tunable monomer composition and properties. The incorporated rigid
spiroacetal units in the polyesters significantly enhanced the glass
transition temperature Tg (up to 72°C) and the storage
moduli according to differential scanning calorimetry (DSC) and dynamic
mechanical analysis (DMA) measurements, respectively. Furthermore, the
obtained polymer films displayed improved oxygen gas barrier by the
incorporation of spiroacetal structures, which indicated their potential
toward food packaging. Finally, we discovered that the obtained
polyesters could be enzymatically depolymerized by the cutinase HiCut
from Humicola insolens, indicating potential biodegradability or enzymatic recyclability. (Less)
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author
; ; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Macromolecular Materials and Engineering
volume
311
issue
5
article number
e00469
pages
15 pages
publisher
Wiley-VCH Verlag
ISSN
1438-7492
DOI
10.1002/mame.202500469
language
English
LU publication?
yes
id
c1d5b7dc-33b7-4f8f-95aa-00bf2bdf8a7a
date added to LUP
2024-12-12 15:35:06
date last changed
2026-05-18 08:49:17
@article{c1d5b7dc-33b7-4f8f-95aa-00bf2bdf8a7a,
  abstract     = {{There has been active research in the development of new rigid biobased <br>
aromatic dicarboxylate monomers that can replace the widely used <br>
fossil-based dimethyl terephthalate in polyester production. In this <br>
work, a new biobased dicarboxylate monomer with a spiroacetal unit was <br>
synthesized from biobased vanillin and pentaerythritol, which aims to <br>
partially or completely replace the fossil-based dimethyl terephthalate <br>
monomer in the production of polyesters. Polyesterification of the new <br>
spirocetal diester monomer, 1,6-hexanediol, in the presence or absence <br>
of dimethyl terephthalate, yielded a series of copolyesters with a <br>
tunable monomer composition and properties. The incorporated rigid <br>
spiroacetal units in the polyesters significantly enhanced the glass <br>
transition temperature <i>T</i><sub>g</sub> (up to 72°C) and the storage<br>
 moduli according to differential scanning calorimetry (DSC) and dynamic<br>
 mechanical analysis (DMA) measurements, respectively. Furthermore, the <br>
obtained polymer films displayed improved oxygen gas barrier by the <br>
incorporation of spiroacetal structures, which indicated their potential<br>
 toward food packaging. Finally, we discovered that the obtained <br>
polyesters could be enzymatically depolymerized by the cutinase HiCut <br>
from <i>Humicola insolens</i>, indicating potential biodegradability or enzymatic recyclability.}},
  author       = {{Mankar, Smita V. and Linares-Pastén, Javier A. and Nguyen, Tam T. and Wahlberg, Jan and Warlin, Niklas and Valsange, Nitin G. and Rehnberg, Nicola and Lundmark, Stefan and Jannasch, Patric and Zhang, Baozhong}},
  issn         = {{1438-7492}},
  language     = {{eng}},
  month        = {{05}},
  number       = {{5}},
  publisher    = {{Wiley-VCH Verlag}},
  series       = {{Macromolecular Materials and Engineering}},
  title        = {{Toward Fully Biobased Polyesters with Spiroacetal Units: Synthesis and Enzymatic Depolymerization}},
  url          = {{http://dx.doi.org/10.1002/mame.202500469}},
  doi          = {{10.1002/mame.202500469}},
  volume       = {{311}},
  year         = {{2026}},
}