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Biodegradable Functional Copolymers
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Biodegradable Functional Copolymers

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Macromolecular Chemistry".

Deadline for manuscript submissions: closed (31 July 2024) | Viewed by 8701

Special Issue Editor

Prof. Dr. Jean Coudane

E-Mail Website
Guest Editor
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Faculté de Pharmacie, Université Montpellier, ENSCM, Bâtiment I, 15 Avenue Charles Flahault, BP14491, 34093 Montpellier Cedex 5, France
Interests: macromolecular chemistry; degradable (co)polymers; chemical modifications; biomedical and environmental fields; biomaterials and drug delivery; aliphatic polyesters
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Many (co)polymers have applications in the environmental or biomedical fields. More and more often, (bio)degradable structures are being sought out, in particular for temporary applications and/or to limit the environmental impact of waste. In order to be able to chemically modify the properties of these (co)polymers, it is helpful or even necessary for their chains to be functionalized. The research on functionalization methods of biodegradable structures, in particular aliphatic polyesters but also polyamides, polyurethanes, etc., is therefore of high interest. These modifications lead to new properties (mechanical properties, degradation, hydrophilicity, compatibility, etc.) with promising applications in the fields of the environment and medicine.

Prof. Dr. Jean Coudane
Guest Editor

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Keywords

  • biodegradable (co)polymers
  • chemical functionalization
  • macromolecular synthesis
  • macromolecular bioconjugates
  • environmental and biomedical applications

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Related Special Issue

Published Papers (5 papers)

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Research

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16 pages, 3744 KiB  
Article
Self-Healable, Transparent, Biodegradable, and Shape Memorable Polyurethanes Derived from Carbon Dioxide-Based Diols
by Xin Huang, Tingting Zhao, Shuanjin Wang, Dongmei Han, Sheng Huang, Hui Guo, Min Xiao and Yuezhong Meng
Molecules 2024, 29(18), 4364; https://doi.org/10.3390/molecules29184364 - 13 Sep 2024
Viewed by 620
Abstract
A series of CO2-based thermoplastic polyurethanes (TPUs) were prepared using CO2-based poly(polycarbonate) diol (PPCDL), 4,4′-methylenebis (cyclohexyl isocyanate) (HMDI), and polypropylene glycol (PPG and 1,4-butanediol (BDO) as the raw materials. The mechanical, thermal, optical, and barrier properties shape memory behaviors, [...] Read more.
A series of CO2-based thermoplastic polyurethanes (TPUs) were prepared using CO2-based poly(polycarbonate) diol (PPCDL), 4,4′-methylenebis (cyclohexyl isocyanate) (HMDI), and polypropylene glycol (PPG and 1,4-butanediol (BDO) as the raw materials. The mechanical, thermal, optical, and barrier properties shape memory behaviors, while biocompatibility and degradation behaviors of the CO2-based TPUs are also systematically investigated. All the synthesized TPUs are highly transparent amorphous polymers, with one glass transition temperature at ~15–45 °C varying with hard segment content and soft segment composition. When PPG is incorporated into the soft segments, the resultant TPUs exhibit excellent self-healing and shape memory performances with the average shape fixity ratio and shape recovery ratio as high as 98.9% and 88.3%, respectively. Furthermore, the CO2-based TPUs also show superior water vapor permeability resistance, good biocompatibility, and good biodegradation properties, demonstrating their pretty competitive potential in the polyurethane industry applications. Full article
(This article belongs to the Special Issue Biodegradable Functional Copolymers)
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15 pages, 10313 KiB  
Article
Long-Term Biodegradation of Polyacrylamide Gel Residues in Mammary Glands: Physico-Chemical Analysis, Chromatographic Detection, and Implications for Chronic Inflammation
by Olga A. Legonkova, Naida O. Sultanova, Victoria V. Stafford, Anastasia A. Zavitaeva, Dmitry S. Kopitsyn, Elena R. Tolboeva, Abdul M. Mahmydov, Vladimir A. Vinokurov, Galina A. Davydova, Natalia B. Svishcheva, Katia Barbaro and Julietta V. Rau
Molecules 2024, 29(14), 3247; https://doi.org/10.3390/molecules29143247 - 9 Jul 2024
Viewed by 902
Abstract
In the past, polyacrylamide hydrogel was a popular choice for breast augmentation filler, and many women underwent mammoplasty with this gel. However, due to frequent complications, the use of polyacrylamide hydrogel in mammoplasty has been banned. Despite this ban, patients experiencing complications still [...] Read more.
In the past, polyacrylamide hydrogel was a popular choice for breast augmentation filler, and many women underwent mammoplasty with this gel. However, due to frequent complications, the use of polyacrylamide hydrogel in mammoplasty has been banned. Despite this ban, patients experiencing complications still seek medical treatment. The aim of this study was to investigate the fate of the polymer over a defined implantation period. Biopsies of breast implants were obtained from patients with 23 and 27 years of post-mammoplasty. These biopsies were meticulously purified from biological impurities and subjected to analysis using IR spectrometry, liquid chromatography—mass spectrometry, gas chromatography, and differential scanning calorimetry. The findings revealed the presence of polyacrylamide hydrogel residues, along with degradation products, within the infected material. Notably, the low-molecular-weight degradation products revealed via gas chromatography are aggressive and toxic substances capable of inducing chronic inflammation. This study sheds light on the long-term consequences of polyacrylamide hydrogel implantation, highlighting the persistence of harmful degradation products and their role in exacerbating patient complications. Full article
(This article belongs to the Special Issue Biodegradable Functional Copolymers)
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14 pages, 2135 KiB  
Article
Influence of Selected Factors on the Adsorption Layer Structure of Polyamino Acids and Their Block Copolymers at the Solid–Aqueous Solution Interface
by Iwona Ostolska and Małgorzata Wiśniewska
Molecules 2023, 28(24), 8080; https://doi.org/10.3390/molecules28248080 - 14 Dec 2023
Cited by 1 | Viewed by 1011
Abstract
The adsorption mechanism of different polymers containing ionic polyamino acids monomers in the chain structure at the solid–liquid interface was investigated. Initially, the influence of molecular weight and solution pH on simple polyamino acids (poly(L-aspartic acid) and poly(L-lysine) binding was determined. Considering the [...] Read more.
The adsorption mechanism of different polymers containing ionic polyamino acids monomers in the chain structure at the solid–liquid interface was investigated. Initially, the influence of molecular weight and solution pH on simple polyamino acids (poly(L-aspartic acid) and poly(L-lysine) binding was determined. Considering the obtained dependencies, the polymer adsorption layer conformation was proposed in the systems containing block copolymers (both diblock and symmetrical triblock) consisting of polypeptide as well as poly(ethylene glycol) fragments. The presented studies focused on the application of two experimental methods. The polymer adsorption was carried out using the batch method and the adsorbate concentration was determined spectrophotometrically. Then, the turbidimetric measurements were taken. The analysis of the obtained results showed that the adsorption process of block copolymers depends on two factors. Firstly, the solution pH determines both the nature of the interactions of the copolymer structural units with the solid surface and the conformation of the polypeptide chains. The second parameter influencing the adsorption layer structure is the ratio of the lengths of both blocks. Introducing a short PEG fragment into the polymer main chain may improve the polymer adsorption properties by increasing the number of interactions with the adsorbent surface. Full article
(This article belongs to the Special Issue Biodegradable Functional Copolymers)
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20 pages, 5707 KiB  
Article
Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
by Lesly Dasilva Wandji Djouonkep, Christian Tatchum Tamo, Belle Elda Simo, Nasiru Issah, Marc Nivic Tchouagtie, Naomie Beolle Songwe Selabi, Ingo Doench, Arnaud Kamdem Tamo, Binqiang Xie and Anayancy Osorio-Madrazo
Molecules 2023, 28(4), 1825; https://doi.org/10.3390/molecules28041825 - 15 Feb 2023
Cited by 7 | Viewed by 2033
Abstract
Volatile global oil prices, owing to the scarcity of fossil resources, have impacted the cost of producing petrochemicals. Therefore, there is a need to seek novel, renewable chemicals from biomass feedstocks that have comparable properties to petrochemicals. In this study, synthesis, thermal and [...] Read more.
Volatile global oil prices, owing to the scarcity of fossil resources, have impacted the cost of producing petrochemicals. Therefore, there is a need to seek novel, renewable chemicals from biomass feedstocks that have comparable properties to petrochemicals. In this study, synthesis, thermal and mechanical properties, and degradability studies of a novel series of sustainable thiophene-based copolyesters like poly(hexylene 2,5-thiophenedicarboxylate-co-bis(2-hydroxyethoxybenzene) (PTBxHy) were conducted via a controlled melt polymerization method. Fourier-transform infrared (FTIR) and nuclear magnetic resonance (1H NMR) spectroscopy techniques elucidated the degree of randomness and structural properties of copolyesters. Meanwhile, gel permeation chromatography (GPC) analysis showed a high average molecular weight in the range of 67.4–78.7 × 103 g/mol. The glass transition temperature (Tg) was between 69.4 and 105.5 °C, and the melting point between 173.7 and 194.2 °C. The synthesized polymers outperformed poly(ethylene 2,5-thiophenedicarboxylate) (PETF) and behaved similarly to polyethylene terephthalate. The copolyesters exhibited a high tensile strength of 46.4–70.5 MPa and a toughness of more than 600%, superior to their corresponding homopolyesters. The copolyesters, which ranged from 1,4-bis(2-hydroxyethyl)benzene thiophenedicarboxylate (TBB)-enriched to hexylene thiophenedicarboxylate (THH)-enriched, offered significant control over crystallinity, thermal and mechanical properties. Enzymatic hydrolysis of synthetized polymers using porcine pancreatic lipase (PP-L) over a short period resulted in significant weight losses of 9.6, 11.4, 30.2, and 35 wt%, as observed by scanning electron microscopy (SEM), with perforations visible on all surfaces of the films. Thus, thiophene-based polyesters with cyclic aromatic structures similar to terephthalic acid (TPA) show great promise as PET mimics. At the same time, PP-L appears to be a promising biocatalyst for the degradation of bioplastic waste and its recycling via re-synthesis processes. Full article
(This article belongs to the Special Issue Biodegradable Functional Copolymers)
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Review

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29 pages, 9636 KiB  
Review
Poly(ε-caprolactone)-Based Graft Copolymers: Synthesis Methods and Applications in the Biomedical Field: A Review
by Jean Coudane, Benjamin Nottelet, Julia Mouton, Xavier Garric and Hélène Van Den Berghe
Molecules 2022, 27(21), 7339; https://doi.org/10.3390/molecules27217339 - 28 Oct 2022
Cited by 20 | Viewed by 3656
Abstract
Synthetic biopolymers are attractive alternatives to biobased polymers, especially because they rarely induce an immune response in a living organism. Poly ε-caprolactone (PCL) is a well-known synthetic aliphatic polyester universally used for many applications, including biomedical and environmental ones. Unlike poly lactic acid [...] Read more.
Synthetic biopolymers are attractive alternatives to biobased polymers, especially because they rarely induce an immune response in a living organism. Poly ε-caprolactone (PCL) is a well-known synthetic aliphatic polyester universally used for many applications, including biomedical and environmental ones. Unlike poly lactic acid (PLA), PCL has no chiral atoms, and it is impossible to play with the stereochemistry to modify its properties. To expand the range of applications for PCL, researchers have investigated the possibility of grafting polymer chains onto the PCL backbone. As the PCL backbone is not functionalized, it must be first functionalized in order to be able to graft reactive groups onto the PCL chain. These reactive groups will then allow the grafting of new reagents and especially new polymer chains. Grafting of polymer chains is mainly carried out by “grafting from” or “grafting onto” methods. In this review we describe the main structures of the graft copolymers produced, their different synthesis methods, and their main characteristics and applications, mainly in the biomedical field. Full article
(This article belongs to the Special Issue Biodegradable Functional Copolymers)
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