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Truxillate polyesters derived from dimethoxycinnamic acid: melt-polycondensation, properties, and hydrolytic and enzymatic degradation

Mitrovic, Isabell LU ; Liblikas, Ilme ; Zalite, Rasmus ; Matt, Livia ; Sedrik, Rauno ; Jannasch, Patric LU orcid and Vares, Lauri (2026) In Materials Today Sustainability 34.
Abstract
We report on the synthesis and characterization of polyesters and copolyesters derived from a rigid aromatic cyclobutane diester monomer, 3,4-dimethoxytruxillic acid dimethyl ester (DMDMTr), prepared via [2 + 2] photodimerization of 3,4-dimethoxycinnamic acid. Using an optimized two-step melt transesterification–polycondensation method, DMDMTr was polymerized with various aliphatic diols to yield polyesters with glass transition temperatures (Tgs) ranging from 52 to 94 °C, depending on the diol structure. Copolyesters obtained by incorporating DMDMTr into poly(butylene furanoate) (PBF) showed a linear increase in Tg with the DMDMTr content, and transitioned from semi-crystalline to fully amorphous... (More)
We report on the synthesis and characterization of polyesters and copolyesters derived from a rigid aromatic cyclobutane diester monomer, 3,4-dimethoxytruxillic acid dimethyl ester (DMDMTr), prepared via [2 + 2] photodimerization of 3,4-dimethoxycinnamic acid. Using an optimized two-step melt transesterification–polycondensation method, DMDMTr was polymerized with various aliphatic diols to yield polyesters with glass transition temperatures (Tgs) ranging from 52 to 94 °C, depending on the diol structure. Copolyesters obtained by incorporating DMDMTr into poly(butylene furanoate) (PBF) showed a linear increase in Tg with the DMDMTr content, and transitioned from semi-crystalline to fully amorphous materials at ∼5 mol% DMDMTr. The polyesters showed stable melt processability and formed colorless transparent films with a thermal stability up to 360 °C. Hydrolytic and enzymatic degradation studies revealed an enhanced degradability of the DMDMTr-containing polyesters compared to PBF. General sustainability aspects such as the E factor and atom economy of the monomer were also evaluated. These findings demonstrate the promise of DMDMTr as a biobased monomer for rigid high-Tg polyester materials. (Less)
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author
; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Materials Today Sustainability
volume
34
article number
101358
pages
10 pages
publisher
Elsevier
external identifiers
  • scopus:105035207451
ISSN
2589-2347
DOI
10.1016/j.mtsust.2026.101358
language
English
LU publication?
yes
id
8b94d34a-a7d0-425e-92e6-d79970e0833e
date added to LUP
2025-10-11 08:58:33
date last changed
2026-04-25 04:01:00
@article{8b94d34a-a7d0-425e-92e6-d79970e0833e,
  abstract     = {{We report on the synthesis and characterization of polyesters and copolyesters derived from a rigid aromatic cyclobutane diester monomer, 3,4-dimethoxytruxillic acid dimethyl ester (DMDMTr), prepared via [2 + 2] photodimerization of 3,4-dimethoxycinnamic acid. Using an optimized two-step melt transesterification–polycondensation method, DMDMTr was polymerized with various aliphatic diols to yield polyesters with glass transition temperatures (<i>T</i><sub>g</sub>s) ranging from 52 to 94 °C, depending on the diol structure. Copolyesters obtained by incorporating DMDMTr into poly(butylene furanoate) (PBF) showed a linear increase in <i>T</i><sub>g</sub> with the DMDMTr content, and transitioned from semi-crystalline to fully amorphous materials at ∼5 mol% DMDMTr. The polyesters showed stable melt processability and formed colorless transparent films with a thermal stability up to 360 °C. Hydrolytic and enzymatic degradation studies revealed an enhanced degradability of the DMDMTr-containing polyesters compared to PBF. General sustainability aspects such as the E factor and atom economy of the monomer were also evaluated. These findings demonstrate the promise of DMDMTr as a biobased monomer for rigid high-<i>T</i><sub>g</sub> polyester materials.}},
  author       = {{Mitrovic, Isabell and Liblikas, Ilme and Zalite, Rasmus and Matt, Livia and Sedrik, Rauno and Jannasch, Patric and Vares, Lauri}},
  issn         = {{2589-2347}},
  language     = {{eng}},
  publisher    = {{Elsevier}},
  series       = {{Materials Today Sustainability}},
  title        = {{Truxillate polyesters derived from dimethoxycinnamic acid: melt-polycondensation, properties, and hydrolytic and enzymatic degradation}},
  url          = {{http://dx.doi.org/10.1016/j.mtsust.2026.101358}},
  doi          = {{10.1016/j.mtsust.2026.101358}},
  volume       = {{34}},
  year         = {{2026}},
}