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Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors

A facile synthesis of isocyanate free polyurethanes (PU) was executed by the reaction of biodegradable cyclic carbonate and sustainable diamines generated via chemical modification. The biodegradable polyol polycaprolactone triol (PCL) was transformed into a new glycerol carbonate derivative, PCL-(C...

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Autores principales: Chelike, Dinesh Kumar, Gurusamy Thangavelu, Senthil A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9766200/
https://www.ncbi.nlm.nih.gov/pubmed/36605652
http://dx.doi.org/10.1039/d2ra05710g
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author Chelike, Dinesh Kumar
Gurusamy Thangavelu, Senthil A.
author_facet Chelike, Dinesh Kumar
Gurusamy Thangavelu, Senthil A.
author_sort Chelike, Dinesh Kumar
collection PubMed
description A facile synthesis of isocyanate free polyurethanes (PU) was executed by the reaction of biodegradable cyclic carbonate and sustainable diamines generated via chemical modification. The biodegradable polyol polycaprolactone triol (PCL) was transformed into a new glycerol carbonate derivative, PCL-(COOGC)(3), and subjected to polyaddition with the diamines linalool diamine (LLDA), isosorbide diamine (ISODA) and hexamethylene diamine (HDA). Polyaddition of PCL-(COOGC)(3) with the above diamine precursors was conducted via a one-pot reaction under catalyst-free reaction conditions prior to film casting. The above precursors were characterized by Fourier-transform infrared (FTIR) and (1)H and (13)C nuclear magnetic resonance spectroscopies, high-resolution mass spectrometry and electrospray ionization matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, whereas the PU films were studied by attenuated total reflectance-FTIR spectroscopy, solid state (13)C NMR, scanning electron microscopy, energy-dispersive X-ray spectroscopy, Raman spectroscopy, X-ray diffractometry, differential scanning calorimetry and thermogravimetric analysis. High onset degradation temperature (T(d)) values were observed for the PU films PU-1 (345.8 °C), PU-2 (309.6 °C) and PU-3 (344.6 °C), and further studies, including cross-link density, water contact angle, swelling behaviour and biodegradation (phosphate-buffered saline medium, pH = 7.2 at 45 °C) measurements, were conducted.
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spelling pubmed-97662002023-01-04 Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors Chelike, Dinesh Kumar Gurusamy Thangavelu, Senthil A. RSC Adv Chemistry A facile synthesis of isocyanate free polyurethanes (PU) was executed by the reaction of biodegradable cyclic carbonate and sustainable diamines generated via chemical modification. The biodegradable polyol polycaprolactone triol (PCL) was transformed into a new glycerol carbonate derivative, PCL-(COOGC)(3), and subjected to polyaddition with the diamines linalool diamine (LLDA), isosorbide diamine (ISODA) and hexamethylene diamine (HDA). Polyaddition of PCL-(COOGC)(3) with the above diamine precursors was conducted via a one-pot reaction under catalyst-free reaction conditions prior to film casting. The above precursors were characterized by Fourier-transform infrared (FTIR) and (1)H and (13)C nuclear magnetic resonance spectroscopies, high-resolution mass spectrometry and electrospray ionization matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, whereas the PU films were studied by attenuated total reflectance-FTIR spectroscopy, solid state (13)C NMR, scanning electron microscopy, energy-dispersive X-ray spectroscopy, Raman spectroscopy, X-ray diffractometry, differential scanning calorimetry and thermogravimetric analysis. High onset degradation temperature (T(d)) values were observed for the PU films PU-1 (345.8 °C), PU-2 (309.6 °C) and PU-3 (344.6 °C), and further studies, including cross-link density, water contact angle, swelling behaviour and biodegradation (phosphate-buffered saline medium, pH = 7.2 at 45 °C) measurements, were conducted. The Royal Society of Chemistry 2022-12-20 /pmc/articles/PMC9766200/ /pubmed/36605652 http://dx.doi.org/10.1039/d2ra05710g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chelike, Dinesh Kumar
Gurusamy Thangavelu, Senthil A.
Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
title Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
title_full Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
title_fullStr Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
title_full_unstemmed Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
title_short Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
title_sort biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9766200/
https://www.ncbi.nlm.nih.gov/pubmed/36605652
http://dx.doi.org/10.1039/d2ra05710g
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AT gurusamythangavelusenthila biodegradableisocyanatefreepolyurethanefilmsviaanoncatalyticroutefacilemodifiedpolycaprolactonetriolandbiobaseddiamineasprecursors