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Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks

In this paper the preparation and detailed characterization of designed polyurethanes (SPURs) are reported for potential biological, biomedical and/or pharmaceutical applications. Importantly, in order to fulfill these goals all reactants and solvents used were selected according to the proposal of...

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Autores principales: Nagy, Lajos, Nagy, Miklós, Vadkerti, Bence, Daróczi, Lajos, Deák, György, Zsuga, Miklós, Kéki, Sándor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6587335/
https://www.ncbi.nlm.nih.gov/pubmed/31067812
http://dx.doi.org/10.3390/polym11050825
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author Nagy, Lajos
Nagy, Miklós
Vadkerti, Bence
Daróczi, Lajos
Deák, György
Zsuga, Miklós
Kéki, Sándor
author_facet Nagy, Lajos
Nagy, Miklós
Vadkerti, Bence
Daróczi, Lajos
Deák, György
Zsuga, Miklós
Kéki, Sándor
author_sort Nagy, Lajos
collection PubMed
description In this paper the preparation and detailed characterization of designed polyurethanes (SPURs) are reported for potential biological, biomedical and/or pharmaceutical applications. Importantly, in order to fulfill these goals all reactants and solvents used were selected according to the proposal of EUR-8 Pharmacopoeia. For the synthesis, a novel strategy was introduced and elaborated. A series of SPUR samples was prepared from poly(ε-caprolactone)-diol, 1,6-hexamethylene diisocyanate and sucrose as a chain extender/crosslinking agent to obtain sucrose containing polyurethanes. In addition, the mol ratios of the sucrose were varied within an order of magnitude. The prepolymers and the products of the syntheses were investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and infrared spectroscopy (IR), respectively. It was found that the reactivity of the eight free hydroxyl groups of sucrose are different, and after curing the SPUR samples at 60 °C no free isocyanate groups can be observed. Furthermore, swelling experiments performed with various solvents of different polarities revealed that the highest degree of swelling took place in dimethyl-sulfoxide. However, low degrees of swelling were recognized in water and hexane. It is important to note that the gel contents were around 90% in all cases, which demonstrate that the crosslinking was almost complete. In addition, the kinetics of swelling were also evaluated and successfully modeled. The crosslink densities were calculated from the data of the swelling experiments by means of the Flory-Rehner equation. Unexpectedly, it was found that the crosslink density decreased with the increasing sucrose content also in line with the results obtained by relaxation modulus experiments and dynamic mechanical analysis (DMA). The Tg and Tm of SPUR samples, determined from DSC and DMA measurements, were around −57 °C and 27 °C, respectively. According to the mechanical tests the SPUR samples showed high elongation at break values, i.e., high flexibilities. Furthermore, the stress-strain curves were also modeled and discussed.
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spelling pubmed-65873352019-07-08 Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks Nagy, Lajos Nagy, Miklós Vadkerti, Bence Daróczi, Lajos Deák, György Zsuga, Miklós Kéki, Sándor Polymers (Basel) Article In this paper the preparation and detailed characterization of designed polyurethanes (SPURs) are reported for potential biological, biomedical and/or pharmaceutical applications. Importantly, in order to fulfill these goals all reactants and solvents used were selected according to the proposal of EUR-8 Pharmacopoeia. For the synthesis, a novel strategy was introduced and elaborated. A series of SPUR samples was prepared from poly(ε-caprolactone)-diol, 1,6-hexamethylene diisocyanate and sucrose as a chain extender/crosslinking agent to obtain sucrose containing polyurethanes. In addition, the mol ratios of the sucrose were varied within an order of magnitude. The prepolymers and the products of the syntheses were investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) and infrared spectroscopy (IR), respectively. It was found that the reactivity of the eight free hydroxyl groups of sucrose are different, and after curing the SPUR samples at 60 °C no free isocyanate groups can be observed. Furthermore, swelling experiments performed with various solvents of different polarities revealed that the highest degree of swelling took place in dimethyl-sulfoxide. However, low degrees of swelling were recognized in water and hexane. It is important to note that the gel contents were around 90% in all cases, which demonstrate that the crosslinking was almost complete. In addition, the kinetics of swelling were also evaluated and successfully modeled. The crosslink densities were calculated from the data of the swelling experiments by means of the Flory-Rehner equation. Unexpectedly, it was found that the crosslink density decreased with the increasing sucrose content also in line with the results obtained by relaxation modulus experiments and dynamic mechanical analysis (DMA). The Tg and Tm of SPUR samples, determined from DSC and DMA measurements, were around −57 °C and 27 °C, respectively. According to the mechanical tests the SPUR samples showed high elongation at break values, i.e., high flexibilities. Furthermore, the stress-strain curves were also modeled and discussed. MDPI 2019-05-07 /pmc/articles/PMC6587335/ /pubmed/31067812 http://dx.doi.org/10.3390/polym11050825 Text en © 2019 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nagy, Lajos
Nagy, Miklós
Vadkerti, Bence
Daróczi, Lajos
Deák, György
Zsuga, Miklós
Kéki, Sándor
Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks
title Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks
title_full Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks
title_fullStr Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks
title_full_unstemmed Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks
title_short Designed Polyurethanes for Potential Biomedical and Pharmaceutical Applications: Novel Synthetic Strategy for Preparing Sucrose Containing Biocompatible and Biodegradable Polyurethane Networks
title_sort designed polyurethanes for potential biomedical and pharmaceutical applications: novel synthetic strategy for preparing sucrose containing biocompatible and biodegradable polyurethane networks
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6587335/
https://www.ncbi.nlm.nih.gov/pubmed/31067812
http://dx.doi.org/10.3390/polym11050825
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