Environmentally friendly polyurethanes based on non-isocyanate synthesis

A series of environmentally friendly non-isocyanate polyurethanes (NIPUs) was synthesized through a polycondensation reaction of as-synthesized semi-bio-based bis-cyclic carbonate with diamine derivatives. The synthesis of biscyclic carbonate was realized, for the first time, from 1-thioglycerol and...

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Main Authors: Afsoon Farzan, Sedigheh Borandeh, Hossein Baniasadi, Jukka Seppälä
Format: Article
Language:English
Published: Budapest University of Technology and Economics 2024-01-01
Series:eXPRESS Polymer Letters
Subjects:
Online Access:http://www.expresspolymlett.com/letolt.php?file=EPL-0012737&mi=cd
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author Afsoon Farzan
Sedigheh Borandeh
Hossein Baniasadi
Jukka Seppälä
author_facet Afsoon Farzan
Sedigheh Borandeh
Hossein Baniasadi
Jukka Seppälä
author_sort Afsoon Farzan
collection DOAJ
description A series of environmentally friendly non-isocyanate polyurethanes (NIPUs) was synthesized through a polycondensation reaction of as-synthesized semi-bio-based bis-cyclic carbonate with diamine derivatives. The synthesis of biscyclic carbonate was realized, for the first time, from 1-thioglycerol and polyethylene glycol diacrylate via thiol-ene click and transcarbonation reaction, respectively. The impacts of using different diamine derivatives on the chemical structural, mechanical properties, thermal stability, and surface wettability of the NIPUs were determined. It was found that the NIPU containing fatty acid-based diamine decomposed at a lower temperature than that of other polymers. Besides, it demonstrated a lower Young’s modulus and a higher tensile strain at break, possibly due to its four-branched structure and greater flexibility. Meanwhile, the NIPU prepared with p-xylylenediamine provided the highest decomposition temperature, owing to an aromatic moiety in the polymer’s backbone, which improved its stiffness and thermal stability. Furthermore, it was understood that the NIPU containing diamino-N-methyldipropyl-amine exhibited a higher Young’s modulus and a lower tensile strain at break, as it had a nitrogen atom in its structure and a trigonal pyramidal configuration with the highest density of hydrogen bonds between polymer chains. Most of the developed NIPUs displayed hydrophobic surface properties, offering promising alternatives to isocyanate-based coating materials.
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spelling doaj-art-61442f2415e94de9ae77c03b6920b7f12025-08-20T03:56:22ZengBudapest University of Technology and EconomicseXPRESS Polymer Letters1788-618X2024-01-011818810110.3144/expresspolymlett.2024.7Environmentally friendly polyurethanes based on non-isocyanate synthesisAfsoon FarzanSedigheh BorandehHossein BaniasadiJukka SeppäläA series of environmentally friendly non-isocyanate polyurethanes (NIPUs) was synthesized through a polycondensation reaction of as-synthesized semi-bio-based bis-cyclic carbonate with diamine derivatives. The synthesis of biscyclic carbonate was realized, for the first time, from 1-thioglycerol and polyethylene glycol diacrylate via thiol-ene click and transcarbonation reaction, respectively. The impacts of using different diamine derivatives on the chemical structural, mechanical properties, thermal stability, and surface wettability of the NIPUs were determined. It was found that the NIPU containing fatty acid-based diamine decomposed at a lower temperature than that of other polymers. Besides, it demonstrated a lower Young’s modulus and a higher tensile strain at break, possibly due to its four-branched structure and greater flexibility. Meanwhile, the NIPU prepared with p-xylylenediamine provided the highest decomposition temperature, owing to an aromatic moiety in the polymer’s backbone, which improved its stiffness and thermal stability. Furthermore, it was understood that the NIPU containing diamino-N-methyldipropyl-amine exhibited a higher Young’s modulus and a lower tensile strain at break, as it had a nitrogen atom in its structure and a trigonal pyramidal configuration with the highest density of hydrogen bonds between polymer chains. Most of the developed NIPUs displayed hydrophobic surface properties, offering promising alternatives to isocyanate-based coating materials.http://www.expresspolymlett.com/letolt.php?file=EPL-0012737&mi=cd biopolymer polymerisation thermal analysis tensile testing wettability x-ray
spellingShingle Afsoon Farzan
Sedigheh Borandeh
Hossein Baniasadi
Jukka Seppälä
Environmentally friendly polyurethanes based on non-isocyanate synthesis
eXPRESS Polymer Letters
biopolymer
polymerisation
thermal analysis
tensile testing
wettability
x-ray
title Environmentally friendly polyurethanes based on non-isocyanate synthesis
title_full Environmentally friendly polyurethanes based on non-isocyanate synthesis
title_fullStr Environmentally friendly polyurethanes based on non-isocyanate synthesis
title_full_unstemmed Environmentally friendly polyurethanes based on non-isocyanate synthesis
title_short Environmentally friendly polyurethanes based on non-isocyanate synthesis
title_sort environmentally friendly polyurethanes based on non isocyanate synthesis
topic biopolymer
polymerisation
thermal analysis
tensile testing
wettability
x-ray
url http://www.expresspolymlett.com/letolt.php?file=EPL-0012737&mi=cd
work_keys_str_mv AT afsoonfarzan environmentallyfriendlypolyurethanesbasedonnonisocyanatesynthesis
AT sedighehborandeh environmentallyfriendlypolyurethanesbasedonnonisocyanatesynthesis
AT hosseinbaniasadi environmentallyfriendlypolyurethanesbasedonnonisocyanatesynthesis
AT jukkaseppala environmentallyfriendlypolyurethanesbasedonnonisocyanatesynthesis