Polyester-Based Materials II

A special issue of Polymers (ISSN 2073-4360). This special issue belongs to the section "Biomacromolecules, Biobased and Biodegradable Polymers".

Deadline for manuscript submissions: 25 July 2024 | Viewed by 12321

Special Issue Editors


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Guest Editor
Faculty of Material Sciences and Engineering, Politehnica University of Bucharest, Bucharest, Romania
Interests: biodegradable polymers; polymer processing technologies; characterization; applications of bio-based materials
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Guest Editor
Petru Poni Institute of Macromolecular Chemistry, Grigore Ghica Voda Alley 41A, 700487 Iasi, Romania
Interests: reactive processing (natural and synthetic polymers); physico-chemical characterization of polymers and composites (rheological, mechanical, thermal, and surface properties); biodegradable polymers; applications of bio-based materials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Polyesters represent one of the most important classes of polymers with an increased demand for them in the current market. In addition to the more well-known materials of polyethylene terephthalate (PET), polybutylene terephthalate (PBT), and polycaprolactone (PCL), which are petroleum-derived polyesters, the versatility of ester linkage has increased the development of novel biobased polyesters and co-polyesters from renewable resources, polylactic acid (PLA) and polyhydroxyalkanoates (PHAs) being the most competitive biodegradable polymers commercialized among them to date. Novel approaches are constantly being proposed to develop new sources for biobased polyesters for diverse applications, as well as to improve the properties of known polyesters and their resulting materials.

The current Special Issue invites original papers and reviews that report on the most valuable discoveries concerning polyester-based materials. Insights into polyester functionalization, copolymerization, surface modification, or the use of a variety of additives or fillers in order to increase the development and performance of polyester-based materials in various industries, such as packaging, automotive, constructions, electronics, textile, or the medical field, are also welcome. Studies regarding environmental impacts and, in particular, the recyclability or (bio)degradation of the polyester-based materials can also be included in this Special Issue.

Dr. Maria Râpă
Dr. Raluca Nicoleta Darie-Niță
Guest Editors

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Keywords

  • bio-based polyesters
  • synthetic polyesters
  • additives
  • bio(degradation)
  • materials
  • characterization
  • applications

Published Papers (7 papers)

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Research

19 pages, 3396 KiB  
Article
Mechanical Properties and Degradation Rate of Poly(Sorbitol Adipate-Co-Dioladipate) Copolymers Obtained with a Catalyst-Free Melt Polycondensation Method
by V. Kavimani, Sivarama Krishna Lakkaboyana, Herri Trilaksana and Leonard I. Atanase
Polymers 2024, 16(4), 499; https://doi.org/10.3390/polym16040499 - 11 Feb 2024
Cited by 1 | Viewed by 812
Abstract
A new family of polyester-based copolymers—poly(sorbitol adipate-co-ethylene glycol adipate) (PSAEG), poly(sorbitol adipate-co-1,4 butane diol adipate) (PSABD), and poly (sorbitol adipate-co-1,6 hexane diol adipate) (PSAHD)—was obtained with a catalyst-free melt polycondensation procedure using the multifunctional non-toxic monomer sorbitol, adipic acid, and diol, which are [...] Read more.
A new family of polyester-based copolymers—poly(sorbitol adipate-co-ethylene glycol adipate) (PSAEG), poly(sorbitol adipate-co-1,4 butane diol adipate) (PSABD), and poly (sorbitol adipate-co-1,6 hexane diol adipate) (PSAHD)—was obtained with a catalyst-free melt polycondensation procedure using the multifunctional non-toxic monomer sorbitol, adipic acid, and diol, which are acceptable to the human metabolism. Synthesized polyesters were characterized by FTIR and 1H NMR spectroscopy. The molecular weight and thermal properties of the polymers were determined by MALDI mass spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis. The degradation rate was investigated, at 37 °C, in 0.1M NaOH (pH 13) and in phosphate-buffered solution (PBS) at pH 7.4. It was found that the polymers degraded faster in NaOH (i.e., in a day) compared to their degradation in PBS, which was much slower (in a week). The highest degradation rate was noticed for the PSAEG sample in both media, whereas PSAHD was the most stable polymer at pH 7.4 and 13. A reduced hydrophilicity of the polymers with diol length was indicated by low swelling percentage and sol content in water and DMSO. Mechanical studies prove that all the polymers are elastomers whose flexibility increases with diol length, shown by the increase in percentage of elongation at break and the decrease in tensile stress and Young’s modulus. These biodegradable copolymers with adaptable physicochemical characteristics might be useful for a broad variety of biological applications by merely varying the length of the diol. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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15 pages, 6215 KiB  
Article
Acidic Metal-Based Functional Ionic Liquids Catalyze the Synthesis of Bio-Based PEF Polyester
by Qiao Zhou, Yuanyuan Zhao, Yafei Shi, Rongrong Zheng and Liying Guo
Polymers 2024, 16(1), 103; https://doi.org/10.3390/polym16010103 - 29 Dec 2023
Viewed by 1168
Abstract
Utilizing triethylenediamine (DA), 1,3-propanesultone (PS), whose ring opens during the formation of the dizwiterion-intermediate DA-2PS, and the metal chlorides XCly, where X = Sn(IV), Zn(II),Al(III), Fe(III) and Mn(II), are used for the synthesis of five kinds of acidic metal-based functionalized ionic liquid catalysts [...] Read more.
Utilizing triethylenediamine (DA), 1,3-propanesultone (PS), whose ring opens during the formation of the dizwiterion-intermediate DA-2PS, and the metal chlorides XCly, where X = Sn(IV), Zn(II),Al(III), Fe(III) and Mn(II), are used for the synthesis of five kinds of acidic metal-based functionalized ionic liquid catalysts ([DA-2PS][XCly]2). Their chemical structures, thermal stability and dual acidic active site were analyzed. We investigated the performance of [DA-2PS][XCly]2 in catalyzing the esterification reaction between 2,5-furandicarboxylic acid (FDCA) and ethylene glycol (EG) to synthesize poly (ethylene 2,5-furandicarboxylate)(PEF). Among the catalysts tested, [DA-2PS][SnCl5]2 exhibited the best catalytic performance under identical process parameters, and the optimal catalyst dosage was determined to be 0.05 mol% based on FDCA. The optimal conditions for the reaction were predicted using response surface methodology: a feed ratio of EG:FDCA = 1.96:1, an esterification temperature of 219.86 °C, a polycondensation temperature of 240.04 °C and a polycondensation time of 6.3 h, with a intrinsic viscosity of 0.67 dL·g−1. The resulting PEF was experimentally verified to exhibit an intrinsic viscosity of 0.68 dL·g−1 and a number average molecular weight of 28,820 g·mol−1. Finally, the structure and thermal properties of PEF were characterized. The results confirmed that PEF possessed the correct structure, exhibited high thermal stability and demonstrated excellent thermal properties. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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13 pages, 20267 KiB  
Article
Photocured Poly(Mannitol Sebacate) with Functional Methacrylic Monomer: Analysis of Physical, Chemical, and Biological Properties
by Víctor Hevilla, Águeda Sonseca, Coro Echeverría, Alexandra Muñoz-Bonilla and Marta Fernández-García
Polymers 2023, 15(6), 1561; https://doi.org/10.3390/polym15061561 - 21 Mar 2023
Cited by 1 | Viewed by 1756
Abstract
In this work, we described the formation of polymeric networks with potential antimicrobial character based on an acrylate oligomer, poly(mannitol sebacate) (PMS), and an enzymatically synthesized methacrylic monomer with thiazole groups (MTA). Networks with different content of MTA were prepared, and further physico-chemically [...] Read more.
In this work, we described the formation of polymeric networks with potential antimicrobial character based on an acrylate oligomer, poly(mannitol sebacate) (PMS), and an enzymatically synthesized methacrylic monomer with thiazole groups (MTA). Networks with different content of MTA were prepared, and further physico-chemically characterized by microhardness, water contact angle measurements, and differential scanning calorimetry. Monomer incorporation into the networks and subsequent quaternization to provide thiazolium moieties affected the mechanical behavior and the surface wettability of the networks. Moreover, the introduction of permanent cationic charges in the network surface could give antimicrobial activity to them. Therefore, the antibacterial behavior and the hemotoxicity were analyzed against Gram-positive and Gram-negative bacteria and red blood cells, respectively. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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24 pages, 3396 KiB  
Article
Thiophene End-Functionalized Oligo-(D,L-Lactide) as a New Electroactive Macromonomer for the “Hairy-Rod” Type Conjugated Polymers Synthesis
by Anca-Dana Bendrea, Luminita Cianga, Demet Göen Colak, Doina Constantinescu and Ioan Cianga
Polymers 2023, 15(5), 1094; https://doi.org/10.3390/polym15051094 - 22 Feb 2023
Viewed by 1872
Abstract
The development of the modern society imposes a fast-growing demand for new advanced functional polymer materials. To this aim, one of the most plausible current methodologies is the end-group functionalization of existing conventional polymers. If the end functional group is able to polymerize, [...] Read more.
The development of the modern society imposes a fast-growing demand for new advanced functional polymer materials. To this aim, one of the most plausible current methodologies is the end-group functionalization of existing conventional polymers. If the end functional group is able to polymerize, this method enables the synthesis of a molecularly complex, grafted architecture that opens the access to a wider range of material properties, as well as tailoring the special functions required for certain applications. In this context, the present paper reports on α-thienyl-ω-hydroxyl-end-groups functionalized oligo-(D,L-lactide) (Th-PDLLA), which was designed to combine the polymerizability and photophysical properties of thiophene with the biocompatibility and biodegradability of poly-(D,L-lactide). Th-PDLLA was synthesized using the path of “functional initiator” in the ring-opening polymerization (ROP) of (D,L)-lactide, assisted by stannous 2-ethyl hexanoate (Sn(oct)2). The results of NMR and FT-IR spectroscopic methods confirmed the Th-PDLLA’s expected structure, while the oligomeric nature of Th-PDLLA, as resulting from the calculations based on 1H-NMR data, is supported by the findings from gel permeation chromatography (GPC) and by the results of the thermal analyses. The behavior of Th-PDLLA in different organic solvents, evaluated by UV–vis and fluorescence spectroscopy, but also by dynamic light scattering (DLS), suggested the presence of colloidal supramolecular structures, underlining the nature of the macromonomer Th-PDLLA as an “shape amphiphile”. To test its functionality, the ability of Th-PDLLA to work as a building block for the synthesis of molecular composites was demonstrated by photoinduced oxidative homopolymerization in the presence of diphenyliodonium salt (DPI). The occurrence of a polymerization process, with the formation of a thiophene-conjugated oligomeric main chain grafted with oligomeric PDLLA, was proven, in addition to the visual changes, by the results of GPC, 1H-NMR, FT-IR, UV–vis and fluorescence measurements. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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13 pages, 2695 KiB  
Article
Synthesis, Thermal Behavior, and Mechanical Properties of Fully Biobased Poly(Hexamethylene 2,5-Furandicarboxylate-Co-Sebacate) Copolyesters
by Shiwei Feng, Zhiguo Jiang and Zhaobin Qiu
Polymers 2023, 15(1), 85; https://doi.org/10.3390/polym15010085 - 25 Dec 2022
Cited by 8 | Viewed by 1601
Abstract
In this research, three fully biobased poly(hexamethylene 2,5-furandicarboxylate-co-sebacate) (PHFSe) copolyesters with low contents of hexamethylene sebacate (HSe) unit (10 mol%, 20 mol%, and 30 mol%) were successfully synthesized through a two-step transesterification/esterification and polycondensation method. The chemical structure and actual composition [...] Read more.
In this research, three fully biobased poly(hexamethylene 2,5-furandicarboxylate-co-sebacate) (PHFSe) copolyesters with low contents of hexamethylene sebacate (HSe) unit (10 mol%, 20 mol%, and 30 mol%) were successfully synthesized through a two-step transesterification/esterification and polycondensation method. The chemical structure and actual composition of PHFSe copolyesters were confirmed by hydrogen nuclear magnetic resonance. The thermal behavior and mechanical property of PHFSe copolyesters were investigated and compared with those of the poly(hexamethylene 2,5-furandicarboxylate) (PHF) homopolymer. Both PHFSe copolyesters and PHF showed the high thermal stability. The basic thermal parameters, including glass transition temperature, melting temperature, and equilibrium melting temperature, gradually decreased with increasing the HSe unit content. PHFSe copolyesters crystallized more slowly than PHF under both the nonisothermal and isothermal melt crystallization conditions; however, they crystallized through the same crystallization mechanism and crystal structure. In addition, the mechanical property, especially the elongation at break of PHFSe copolyesters, was obviously improved when the HSe unit content was greater than 10 mol%. In brief, the thermal and mechanical properties of PHF may be easily tuned by changing the HSe unit content to meet various practical end-use requirements. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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19 pages, 3063 KiB  
Article
Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (P(3HB-co-3HV))/Bacterial Cellulose (BC) Biocomposites for Potential Use in Biomedical Applications
by Maria Râpă, Laura Mihaela Stefan, Ana-Maria Seciu-Grama, Alexandra Gaspar-Pintiliescu, Ecaterina Matei, Cătălin Zaharia, Paul Octavian Stănescu and Cristian Predescu
Polymers 2022, 14(24), 5544; https://doi.org/10.3390/polym14245544 - 18 Dec 2022
Cited by 5 | Viewed by 2306
Abstract
The aim of this study was to obtain biocomposites consisting of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV), bacterial cellulose (BC) and α-tocopherol by a melt processing technique for potential use in biomedical applications. The melt processing and roughness of biocomposites were evaluated and compared to [...] Read more.
The aim of this study was to obtain biocomposites consisting of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV), bacterial cellulose (BC) and α-tocopherol by a melt processing technique for potential use in biomedical applications. The melt processing and roughness of biocomposites were evaluated and compared to sample without BC. The degradation rate of PHBV/BC biocomposites was measured in phosphate buffer saline (PBS) by determining the mass variation and evidencing of thermal and structural changes by differential scanning calorimetry (DSC) and attenuated total reflectance-Fourier transformed infrared spectrometry (ATR-FTIR). The cell viability, cell morphology, cell cycle distribution and total collagen content were investigated on murine NCTC fibroblasts. Overall, the adding of BC to polyester matrix led to an adequate melt processing of biocomposites and increased surface roughness and cytocompatibility, allowing the cells to secrete the extracellular matrix (collagen) and stimulate cell proliferation. Results showed that the PHBV/BC biocomposites were favorable for long-term degradation and could be used for the design of medical devices with controlled degradability. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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11 pages, 1885 KiB  
Article
Formation and Characterization of Oregano Essential Oil Nanocapsules Applied onto Polyester Textile
by Carla Salinas, Manuel J. Lis, Luisa Coderch and Meritxell Martí
Polymers 2022, 14(23), 5188; https://doi.org/10.3390/polym14235188 - 29 Nov 2022
Viewed by 1857
Abstract
Oregano essential oil was encapsulated in poly-ϵ-caprolactone nanoparticles by a nanoprecipitation method using glycerin as a moisturizer. Nanocapsule characterization was performed by measuring the particle size, colloidal stability and encapsulation efficiency using dynamic light scattering, UV–Vis spectrophotometry and scanning electron microscopy (SEM). The [...] Read more.
Oregano essential oil was encapsulated in poly-ϵ-caprolactone nanoparticles by a nanoprecipitation method using glycerin as a moisturizer. Nanocapsule characterization was performed by measuring the particle size, colloidal stability and encapsulation efficiency using dynamic light scattering, UV–Vis spectrophotometry and scanning electron microscopy (SEM). The nanoparticles had a mean particle size of 235 nm with a monomodal distribution. In addition, a low polydispersity index was obtained, as well as a negative zeta potential of −36.3 mV and an encapsulation efficiency of 75.54%. Nanocapsules were applied to polyester textiles through bath exhaustion and foulard processing. Citric acid and a resin were applied as crosslinking agents to improve the nanocapsules’ adhesion to the fabric. The adsorption, desorption, moisture content and essential oil extraction were evaluated to determine the affinity between the nanocapsules and the polyester. The adsorption was higher when the citric acid and the resin were applied. When standard oregano nanocapsules were used, almost all of the impregnated nanoparticles were removed when washed with water. The moisture content was evaluated for treated and non-treated textiles. There was a significant increase in the moisture content of the treated polyester compared to the non-treated polyester, which indicates that the polyester hydrophilicity increased with an important absorption of the essential oil nanocapsules; this can improve fabric comfort and probably promote antibacterial properties. Full article
(This article belongs to the Special Issue Polyester-Based Materials II)
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