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Short-Loop Chemical Recycling via Telechelic Polymers for Biobased Polyesters with Spiroacetal Units

Mankar, Smita V. LU ; Wahlberg, Jan ; Warlin, Niklas LU ; Valsange, Nitin G. LU ; Rehnberg, Nicola LU orcid ; Lundmark, Stefan ; Jannasch, Patric LU orcid and Zhang, Baozhong LU (2023) In ACS Sustainable Chemistry & Engineering 11(13). p.5135-5146
Abstract
Spirocyclic acetal structures have recently received growing attention
in polymer science due to their dual potential to raise the glass
transition temperature (Tg) and enable chemical
recycling of biobased polymers. In the present work, a vanillin-based
diol with a spirocyclic acetal structure was incorporated in a series of
rigid amorphous polyesters based on neopentyl glycol and dimethyl
terephthalate (DMT). Up to 50 mol % of spirocyclic diol (with respect to
DMT) could be incorporated in the copolyesters, but a reasonably high
molecular weight was only achieved when ≤30 mol % of the spirocyclic
diol was used. The presence of the spiroacetal units in the polyesters
not... (More)
Spirocyclic acetal structures have recently received growing attention
in polymer science due to their dual potential to raise the glass
transition temperature (Tg) and enable chemical
recycling of biobased polymers. In the present work, a vanillin-based
diol with a spirocyclic acetal structure was incorporated in a series of
rigid amorphous polyesters based on neopentyl glycol and dimethyl
terephthalate (DMT). Up to 50 mol % of spirocyclic diol (with respect to
DMT) could be incorporated in the copolyesters, but a reasonably high
molecular weight was only achieved when ≤30 mol % of the spirocyclic
diol was used. The presence of the spiroacetal units in the polyesters
not only enhanced the Tg (up to 103 °C) and thermal stability (T5
≥ 300 °C) but also the oxygen barrier of solution-cast films. We found
that the acetal units in the copolyesters could be selectively
hydrolyzed under acidic conditions while virtually retaining all of the
ester bonds in the polymer backbone. After acidic hydrolysis, telechelic
polymers exclusively terminated by two aldehyde end groups were
obtained. In this work, we have demonstrated that these telechelic
polyesters can be conveniently converted back into poly(acetal-ester)s
via cycloacetalization reactions with pentaerythritol. (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
ACS Sustainable Chemistry & Engineering
volume
11
issue
13
pages
12 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85151339003
ISSN
2168-0485
DOI
10.1021/acssuschemeng.2c07176
language
English
LU publication?
yes
additional info
Publication Date: March 23, 2023
id
6794189e-45c8-4aaf-bc35-7949457cee19
date added to LUP
2020-12-02 19:41:22
date last changed
2023-04-27 07:24:21
@article{6794189e-45c8-4aaf-bc35-7949457cee19,
  abstract     = {{Spirocyclic acetal structures have recently received growing attention <br>
in polymer science due to their dual potential to raise the glass <br>
transition temperature (<i>T</i><sub>g</sub>) and enable chemical <br>
recycling of biobased polymers. In the present work, a vanillin-based <br>
diol with a spirocyclic acetal structure was incorporated in a series of<br>
 rigid amorphous polyesters based on neopentyl glycol and dimethyl <br>
terephthalate (DMT). Up to 50 mol % of spirocyclic diol (with respect to<br>
 DMT) could be incorporated in the copolyesters, but a reasonably high <br>
molecular weight was only achieved when ≤30 mol % of the spirocyclic <br>
diol was used. The presence of the spiroacetal units in the polyesters <br>
not only enhanced the <i>T</i><sub>g</sub> (up to 103 °C) and thermal stability (<i>T</i><sub>5</sub><br>
 ≥ 300 °C) but also the oxygen barrier of solution-cast films. We found <br>
that the acetal units in the copolyesters could be selectively <br>
hydrolyzed under acidic conditions while virtually retaining all of the <br>
ester bonds in the polymer backbone. After acidic hydrolysis, telechelic<br>
 polymers exclusively terminated by two aldehyde end groups were <br>
obtained. In this work, we have demonstrated that these telechelic <br>
polyesters can be conveniently converted back into poly(acetal-ester)s <br>
via cycloacetalization reactions with pentaerythritol.}},
  author       = {{Mankar, Smita V. and Wahlberg, Jan and Warlin, Niklas and Valsange, Nitin G. and Rehnberg, Nicola and Lundmark, Stefan and Jannasch, Patric and Zhang, Baozhong}},
  issn         = {{2168-0485}},
  language     = {{eng}},
  number       = {{13}},
  pages        = {{5135--5146}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{ACS Sustainable Chemistry & Engineering}},
  title        = {{Short-Loop Chemical Recycling via Telechelic Polymers for Biobased Polyesters with Spiroacetal Units}},
  url          = {{http://dx.doi.org/10.1021/acssuschemeng.2c07176}},
  doi          = {{10.1021/acssuschemeng.2c07176}},
  volume       = {{11}},
  year         = {{2023}},
}