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Synthesis and melt-spinning of partly bio-based thermoplastic poly(cycloacetal-urethane)s toward sustainable textiles

Warlin, Niklas LU ; Nilsson, Erik ; Guo, Zengwei ; Mankar, Smita V. LU ; Valsange, Nitin LU ; Rehnberg, Nicola LU orcid ; Lundmark, Stefan ; Jannasch, Patric LU orcid and Zhang, Baozhong LU (2021) In Polymer Chemistry 12(34). p.4942-4953
Abstract
A rigid diol with a cyclic acetal structure was synthesized by facile acetalation of fructose-based 5-hydroxymethyl furfural (HMF) and partly bio-based di-trimethylolpropane (di-TMP). This diol (Monomer T) was copolymerized with potentially biobased flexible polytetrahydrofuran and diisocyanates to prepare thermoplastic poly(cycloacetal-urethane)s. A modified one step solution polymerization protocol resulted in relatively high molecular weights (Mn ~ 41.5 -98.9 kDa). All the obtained poly(cycloacetal-urethane)s were amorphous with tuneable glass transition temperatures up to 104 °C. Thermogravimetric analysis indicated that these polymers were thermally stable up to 253 °C and had a relatively high pyrolysis char... (More)
A rigid diol with a cyclic acetal structure was synthesized by facile acetalation of fructose-based 5-hydroxymethyl furfural (HMF) and partly bio-based di-trimethylolpropane (di-TMP). This diol (Monomer T) was copolymerized with potentially biobased flexible polytetrahydrofuran and diisocyanates to prepare thermoplastic poly(cycloacetal-urethane)s. A modified one step solution polymerization protocol resulted in relatively high molecular weights (Mn ~ 41.5 -98.9 kDa). All the obtained poly(cycloacetal-urethane)s were amorphous with tuneable glass transition temperatures up to 104 °C. Thermogravimetric analysis indicated that these polymers were thermally stable up to 253 °C and had a relatively high pyrolysis char residue, which may indicate potential inherent flame resistance. Melt rheology measurements were performed to determine a suitable processing window between 165-186 °C, after which the polymer was successfully melt-spun into ~150 meters of homogeneous fibres at 185 °C. The resulting fibres could be readily hydrolysed under acidic conditions, resulting in partial
recovery of the original chemical building blocks. (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
Polymer Chemistry
volume
12
issue
34
pages
4942 - 4953
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85114348253
ISSN
1759-9954
DOI
10.1039/D1PY00450F
project
STEPS – Sustainable Plastics and Transition Pathways, Phase 2
language
English
LU publication?
yes
additional info
First published 10 Aug 2021
id
8e8d3aad-262e-4cca-ae82-a2e1b094840d
alternative location
https://pubs.rsc.org/en/content/articlelanding/2021/py/d1py00450f
date added to LUP
2020-11-29 20:34:52
date last changed
2022-04-26 22:15:43
@article{8e8d3aad-262e-4cca-ae82-a2e1b094840d,
  abstract     = {{A rigid diol with a cyclic acetal structure was synthesized by facile acetalation of fructose-based 5-hydroxymethyl furfural (HMF) and partly bio-based di-trimethylolpropane (di-TMP). This diol (Monomer T) was copolymerized with potentially biobased flexible polytetrahydrofuran and diisocyanates to prepare thermoplastic poly(cycloacetal-urethane)s. A modified one step solution polymerization protocol resulted in relatively high molecular weights (<i>M<sub>n</sub></i> ~ 41.5 -98.9 kDa). All the obtained poly(cycloacetal-urethane)s were amorphous with tuneable glass transition temperatures up to 104 °C. Thermogravimetric analysis indicated that these polymers were thermally stable up to 253 °C and had a relatively high pyrolysis char residue, which may indicate potential inherent flame resistance. Melt rheology measurements were performed to determine a suitable processing window between 165-186 °C, after which the polymer was successfully melt-spun into ~150 meters of homogeneous fibres at 185 °C. The resulting fibres could be readily hydrolysed under acidic conditions, resulting in partial<br/>recovery of the original chemical building blocks.}},
  author       = {{Warlin, Niklas and Nilsson, Erik and Guo, Zengwei and Mankar, Smita V. and Valsange, Nitin and Rehnberg, Nicola and Lundmark, Stefan and Jannasch, Patric and Zhang, Baozhong}},
  issn         = {{1759-9954}},
  language     = {{eng}},
  number       = {{34}},
  pages        = {{4942--4953}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Polymer Chemistry}},
  title        = {{Synthesis and melt-spinning of partly bio-based thermoplastic poly(cycloacetal-urethane)s toward sustainable textiles}},
  url          = {{http://dx.doi.org/10.1039/D1PY00450F}},
  doi          = {{10.1039/D1PY00450F}},
  volume       = {{12}},
  year         = {{2021}},
}