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High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)

Polyesters with a high glass transition temperature above 130 °C were obtained from limonene oxide (LO) or vinylcyclohexene oxide (VCHO) and phthalic anhydride (PA) in the presence of commercial salen-type complexes with different metals—Cr, Al, and Mn—as catalysts in combination with 4-(dimethylami...

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Autores principales: Silvano, Selena, Proverbio, Matteo, Vignali, Adriano, Bertini, Fabio, Boggioni, Laura
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10347009/
https://www.ncbi.nlm.nih.gov/pubmed/37447447
http://dx.doi.org/10.3390/polym15132801
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author Silvano, Selena
Proverbio, Matteo
Vignali, Adriano
Bertini, Fabio
Boggioni, Laura
author_facet Silvano, Selena
Proverbio, Matteo
Vignali, Adriano
Bertini, Fabio
Boggioni, Laura
author_sort Silvano, Selena
collection PubMed
description Polyesters with a high glass transition temperature above 130 °C were obtained from limonene oxide (LO) or vinylcyclohexene oxide (VCHO) and phthalic anhydride (PA) in the presence of commercial salen-type complexes with different metals—Cr, Al, and Mn—as catalysts in combination with 4-(dimethylamino) pyridine (DMAP), bis-(triphenylphosphorydine) ammonium chloride (PPNCl), and bis-(triphenylphosphoranylidene)ammonium azide (PPNN(3)) as cocatalysts via alternating ring-opening copolymerization (ROCOP). The effects of the time of precontact between the catalyst and cocatalyst and the polymerization time on the productivity, molar mass (M(w)), and glass transition temperature (T(g)) were evaluated. The polyesters were characterized by a molar mass (M(w)) of up to 14.0 kg/mol, a narrow dispersity T(g) of up to 136 °C, and low (<3 mol%) polyether units. For poly(LO-alt-PA) copolymers, biodegradation tests were performed according to ISO 14851 using the respirometric biochemical oxygen demand method. Moreover, the vinyl double bond present in the poly(LO-alt-PA) copolymer chain was functionalized using three different thiols, methyl-3-mercaptopropionate, isooctyl-3-mercaptopropionate, and butyl-3-mercaptopropionate, via a click chemistry reaction. The thermal properties of poly(LO-alt-PA), poly(VCHO-alt-PA) and thiol-modified poly(LO-alt-PA) copolymers were extensively studied by DSC and TGA. Some preliminary compression molding tests were also conducted.
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spelling pubmed-103470092023-07-15 High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP) Silvano, Selena Proverbio, Matteo Vignali, Adriano Bertini, Fabio Boggioni, Laura Polymers (Basel) Article Polyesters with a high glass transition temperature above 130 °C were obtained from limonene oxide (LO) or vinylcyclohexene oxide (VCHO) and phthalic anhydride (PA) in the presence of commercial salen-type complexes with different metals—Cr, Al, and Mn—as catalysts in combination with 4-(dimethylamino) pyridine (DMAP), bis-(triphenylphosphorydine) ammonium chloride (PPNCl), and bis-(triphenylphosphoranylidene)ammonium azide (PPNN(3)) as cocatalysts via alternating ring-opening copolymerization (ROCOP). The effects of the time of precontact between the catalyst and cocatalyst and the polymerization time on the productivity, molar mass (M(w)), and glass transition temperature (T(g)) were evaluated. The polyesters were characterized by a molar mass (M(w)) of up to 14.0 kg/mol, a narrow dispersity T(g) of up to 136 °C, and low (<3 mol%) polyether units. For poly(LO-alt-PA) copolymers, biodegradation tests were performed according to ISO 14851 using the respirometric biochemical oxygen demand method. Moreover, the vinyl double bond present in the poly(LO-alt-PA) copolymer chain was functionalized using three different thiols, methyl-3-mercaptopropionate, isooctyl-3-mercaptopropionate, and butyl-3-mercaptopropionate, via a click chemistry reaction. The thermal properties of poly(LO-alt-PA), poly(VCHO-alt-PA) and thiol-modified poly(LO-alt-PA) copolymers were extensively studied by DSC and TGA. Some preliminary compression molding tests were also conducted. MDPI 2023-06-24 /pmc/articles/PMC10347009/ /pubmed/37447447 http://dx.doi.org/10.3390/polym15132801 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Silvano, Selena
Proverbio, Matteo
Vignali, Adriano
Bertini, Fabio
Boggioni, Laura
High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)
title High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)
title_full High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)
title_fullStr High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)
title_full_unstemmed High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)
title_short High-Glass-Transition Polyesters Produced with Phthalic Anhydride and Epoxides by Ring-Opening Copolymerization (ROCOP)
title_sort high-glass-transition polyesters produced with phthalic anhydride and epoxides by ring-opening copolymerization (rocop)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10347009/
https://www.ncbi.nlm.nih.gov/pubmed/37447447
http://dx.doi.org/10.3390/polym15132801
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