Thermoresponsive behavior of non-isocyanate poly(hydroxyl)urethane for biomedical composite materials

Zhao, Yanzhi; Xia, Xue; Zhou, Juying; Zhong-jing, Huang; Lei, Fuhou; Tan, Xuecai; Yu, Dingshan; Zhu, Yong; Xu, Haowen

doi:10.1007/s42114-021-00379-x

Cited by 9 publications

(7 citation statements)

References 37 publications

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“…This is also the case for segmented PPG–poly(amide HU) electrospun as fibrous mats . Finally, this green chemistry reaction of a cyclic carbonate with an amine was applied to link the blocks of the thermoresponsive PEG–HU–PPG–HU–PEG triblock copolymers, and hemocompatibility tests performed on the latter demonstrated that the hydroxy-urethane junction did not alter their hemocompatibility, showing the high potential of these NIPUs for cardiovascular applications …”

Section: Introductionmentioning

confidence: 92%

“…45 Finally, this green chemistry reaction of a cyclic carbonate with an amine was applied to link the blocks of the thermoresponsive PEG−HU−PPG−HU− PEG triblock copolymers, and hemocompatibility tests performed on the latter demonstrated that the hydroxyurethane junction did not alter their hemocompatibility, showing the high potential of these NIPUs for cardiovascular applications. 46 In this work, we apply this new green chemistry approach, i.e., the reaction of an unsaturated CO 2 -sourced cyclic carbonate with an alcohol 47 for the functionalization of a PPG−PHU in order to allow its post-photo-cross-linking. Therefore, we exploit an easily accessible CO 2 -based 5membered cyclic carbonate, namely, αCC (see Scheme 1), for the preparation of PPG-carbonate-based NIPUs carrying pendant unsaturations.…”

Section: Introductionmentioning

confidence: 99%

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Design of 3D-Photoprintable, Bio-, and Hemocompatible Nonisocyanate Polyurethane Elastomers for Biomedical Implants

Pierrard,

Melo,

Thijssen

et al. 2024

Biomacromolecules

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Polyurethanes (PUs) have adjustable mechanical properties, making them suitable for a wide range of applications, including in the biomedical field. Historically, these PUs have been synthesized from isocyanates, which are toxic compounds to handle. This has encouraged the search for safer and more environmentally friendly synthetic routes, leading today to the production of nonisocyanate polyurethanes (NIPUs). Among these NIPUs, polyhydroxyurethanes (PHUs) bear additional hydroxyl groups, which are particularly attractive for derivatizing and adjusting their physicochemical properties. In this paper, polyether-based NIPU elastomers with variable stiffness are designed by functionalizing the hydroxyl groups of a poly-(propylene glycol)−PHU by a cyclic carbonate carrying a pendant unsaturation, enabling them to be post-photo-cross-linked with polythiols (thiol−ene). Elastomers with remarkable mechanical properties whose stiffness can be adjusted are obtained. Thanks to the unique viscous properties of these PHU derivatives and their short gel times observed by rheology experiments, formulations for light-based three-dimensional (3D) printing have been developed. Objects were 3D-printed by digital light processing with a resolution down to the micrometer scale, demonstrating their ability to target various designs of prime importance for personalized medicine. In vitro biocompatibility tests have confirmed the noncytotoxicity of these materials for human fibroblasts. In vitro hemocompatibility tests have revealed that they do not induce hemolytic effects, they do not increase platelet adhesion, nor activate coagulation, demonstrating their potential for future applications in the cardiovascular field.

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Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Design of 3D-Photoprintable, Bio-, and Hemocompatible Nonisocyanate Polyurethane Elastomers for Biomedical Implants

Pierrard,

Melo,

Thijssen

et al. 2024

Biomacromolecules

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“…PPOBC and PEGBC are oligomeric bis‐5CCs that are derived from CO 2 cycloaddition to terminal diglycidyl ethers (DGEs) of propylene oxide and ethylene oxide oligomers, respectively. PPOBC oligomers derived from commercially available DGEs with a molecular weight between 380 and 640 g·mol –1 have been applied for the preparation of PHU‐containing hybrid materials such as hydroxyurethane methacrylate thermosets, [ 126 ] thermoresponsive biocompatible poly(hydroxyl)urethanes [ 127 ] and photoresins for 3D printing. [ 128 ] PEGBC , prepared through an analogous strategy as for PPOBC , was recently used for the synthesis of isocyanate‐free polyurethane hydrogels, [ 129 ] adhesives, [ 130 ] water‐soluble PHUs [ 131 ] and amphiphilic PHUs.…”

Section: Overview Of Multi‐5ccsmentioning

confidence: 99%

Polyhydroxyurethanes from Biobased Monomers and CO₂: A Bridge between Sustainable Chemistry and CO₂ Utilization^†

Theerathanagorn,

Kessaratikoon,

Rehman

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryPolyhydroxyurethanes (PHUs) have received considerable attention in the last decade as potential alternatives to traditional phosgene‐based polyurethanes (PUs). The development of suitable 5CC (five membered‐ring cyclic carbonate) precursors bearing multiple carbonate moieties (multi‐5CCs) is a key requisite for preparing PHUs by polyaddition reaction with bis‐ or polyamines. Producing sustainable PHUs from CO2‐based five‐membered cyclic carbonates (5CCs) obtained from biobased epoxides is a valuable strategy to bridge CO2 utilization and the upcycling of renewable substrates. In this context, while many multi‐5CC monomers reported in the literature are oil‐based, recent efforts have led to the development of a large variety of multifunctional 5CCs that are produced by the combination of CO2 and renewable resources such as fatty acids and vegetable oils, lignin, terpenes, and sugars. In this work, recent crucial advances (2019—2023) on PHUs prepared from bis‐ and multi‐5CCs produced from CO2 and (partially/potentially) biobased substrates are reviewed with respect to their synthesis, thermal and mechanical properties, and their recent, emerging applications.

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“…TPUs are generally synthesized through the reaction of isocyanates, polyols, and chain extenders, in the presence of tin-based catalysts. The principal limitation of this route is the high toxicity of isocyanate compounds causing irreversible environmental and human health damage. − Isocyanates are not completely consumed during the polymerization process, and traces of isocyanate residues were detected in the final polyurethanes. , Tin-based catalysts, for example, dibutyl-tin-dilaurate (DBTDL), are not removed after the polymerization process and can result in toxicity. , Therefore, synthesis routes for TPUs excluding isocyanates and tin-based catalysts have attracted great interest, especially for the fabrication of biomedical materials, − food packaging, , and children products.…”

Section: Introductionmentioning

confidence: 99%

“… 4 , 5 Tin-based catalysts, for example, dibutyl-tin-dilaurate (DBTDL), are not removed after the polymerization process and can result in toxicity. 6 , 7 Therefore, synthesis routes for TPUs excluding isocyanates and tin-based catalysts have attracted great interest, especially for the fabrication of biomedical materials, 8 − 10 food packaging, 11 , 12 and children products.…”

Section: Introductionmentioning

confidence: 99%

Green Chemistry for Biomimetic Materials: Synthesis and Electrospinning of High-Molecular-Weight Polycarbonate-Based Nonisocyanate Polyurethanes

et al. 2022

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Conventional synthesis routes for thermoplastic polyurethanes (TPUs) still require the use of isocyanates and tinbased catalysts, which pose considerable safety and environmental hazards. To reduce both the ecological footprint and human health dangers for nonwoven TPU scaffolds, it is key to establish a green synthesis route, which eliminates the use of these toxic compounds and results in biocompatible TPUs with facile processability. In this study, we developed high-molecular-weight nonisocyanate polyurethanes (NIPUs) through transurethanization of 1,6hexanedicarbamate with polycarbonate diols (PCDLs). Various molecular weights of PCDL were employed to maximize the molecular weight of NIPUs and consequently facilitate their electrospinnability. The synthesized NIPUs were characterized by nuclear magnetic resonance, Fourier-transform infrared spectroscopy, gel permeation chromatography, and differential scanning calorimetry. The highest achieved molecular weight (M w ) was 58,600 g/mol. The NIPUs were consecutively electrospun into fibrous scaffolds with fiber diameters in the submicron range, as shown by scanning electron microscopy (SEM). To assess the suitability of electrospun NIPU mats as a possible biomimetic load-bearing pericardial substitute in cardiac tissue engineering, their cytotoxicity was investigated in vitro using primary human fibroblasts and a human epithelial cell line. The bare NIPU mats did not need further biofunctionalization to enhance cell adhesion, as it was not outperformed by collagen-functionalized NIPU mats and hence showed that the NIPU mats possess a great potential for use in biomimetic scaffolds.

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Thermoresponsive behavior of non-isocyanate poly(hydroxyl)urethane for biomedical composite materials

Cited by 9 publications

References 37 publications

Design of 3D-Photoprintable, Bio-, and Hemocompatible Nonisocyanate Polyurethane Elastomers for Biomedical Implants

Design of 3D-Photoprintable, Bio-, and Hemocompatible Nonisocyanate Polyurethane Elastomers for Biomedical Implants

Polyhydroxyurethanes from Biobased Monomers and CO₂: A Bridge between Sustainable Chemistry and CO₂ Utilization^†

Green Chemistry for Biomimetic Materials: Synthesis and Electrospinning of High-Molecular-Weight Polycarbonate-Based Nonisocyanate Polyurethanes

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Thermoresponsive behavior of non-isocyanate poly(hydroxyl)urethane for biomedical composite materials

Cited by 9 publications

References 37 publications

Design of 3D-Photoprintable, Bio-, and Hemocompatible Nonisocyanate Polyurethane Elastomers for Biomedical Implants

Design of 3D-Photoprintable, Bio-, and Hemocompatible Nonisocyanate Polyurethane Elastomers for Biomedical Implants

Polyhydroxyurethanes from Biobased Monomers and CO2: A Bridge between Sustainable Chemistry and CO2 Utilization†

Green Chemistry for Biomimetic Materials: Synthesis and Electrospinning of High-Molecular-Weight Polycarbonate-Based Nonisocyanate Polyurethanes

Contact Info

Product

Resources

About

Polyhydroxyurethanes from Biobased Monomers and CO₂: A Bridge between Sustainable Chemistry and CO₂ Utilization^†