Biodegradable isocyanate-free polyurethane films <i>via</i> a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors

Chelike, Dinesh Kumar; Andavan, Gurusamy Thangavelu Senthil

doi:10.1039/d2ra05710g

Cited by 9 publications

(8 citation statements)

References 58 publications

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“…From Figure b, the aminolysis of polyurethane is confirmed by the induced smooth broad peak at 22.5°, and sharp crystalline peaks at 21.9 and 23.9° confirm the perfect blending of PCL. The PU and PU/PCL films confirm the amorphous nature of polyurethane at 20.4° as a broad valley; after the modification with PCL, the amorphous nature of PU changed into semicrystalline at 21.9 and 23.5°, as shown in Figure S2, due to the presence of PCL. Thus, the XRD analysis proves that the material has not undergone a complete loss of its nature; rather, there is clear evidence of a slight shift in its crystalline nature.…”

Section: Resultsmentioning

confidence: 65%

Sustainable Routed Mxene-Based Aminolyzed PU/PCL Film for Increased Oxidative Stress and a pH-Sensitive Drug Delivery System for Anticancer Therapy

Bose,

Danagody,

Rajappan

et al. 2023

ACS Appl. Bio Mater.

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A remarkable challenge in the anticancer drug delivery system is developing an implantable system that can improve the chemotherapeutic effect. Polyurethane is an excellent implantable substrate, with flaws in hydrophobicity. We modified polyurethane via the chemical aminolysis technique to enhance the wettability and protein interaction. The created pores can release the rutin complex incorporated in the polyurethane matrix. In this work, the hybrid polymer matrix consists of Mxene synthesized via a sustainable and simple method by introducing a toxic-free MAX phase and etchants. The incorporation of Mxene and PCL can enhance physicochemical and biological compatibility. Sustainable Mxene increases oxidative stress, cell death, and antibacterial activity, which also resulted in the Mxene@APU/PCL film. Meanwhile, the drug release with respect to pH sensitivity was demonstrated in which Mxene and Mxene@APU/PCL films showed the highest release at pH 5.2; this indicates that the prepared Mxene and aminolyzed polyurethane can function according to the biological system and release the drug from the polymer matrix on slow degradation and swellability. The Mxene and Mxene@APU/PCL films showed 93.2% drug release with oxidative stress on THP-1 cells, which causes rupturing and apoptosis of cancerous cells. The Mxene@APU/PCL film can show great potential in future implantable anticancer drug delivery systems.

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Section: Resultsmentioning

confidence: 65%

Sustainable Routed Mxene-Based Aminolyzed PU/PCL Film for Increased Oxidative Stress and a pH-Sensitive Drug Delivery System for Anticancer Therapy

Bose,

Danagody,

Rajappan

et al. 2023

ACS Appl. Bio Mater.

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“…Furthermore, the XRD patterns of the crafted PBU, showcased in Figure 2d, mirror the diffraction patterns frequently seen in other urethane-based polymer films, predominantly characterized by a singular, expansive peak around 2θ = 20°. 36 The DA reaction emerges as a cornerstone in the curing mechanism of PBU within the scope of this research. As elucidated in Figure 2e, the DA reaction, in essence, represents a cycloaddition process.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

“…Diving into the C 1s XPS spectrum deconvolution for the PBU, peaks indicative of C–C, C–H, and C–O bonds manifest at 285.28 and 286.5 eV, aligning harmoniously with the observations from the FT-IR spectra (as seen in Figure c). Furthermore, the XRD patterns of the crafted PBU, showcased in Figure d, mirror the diffraction patterns frequently seen in other urethane-based polymer films, predominantly characterized by a singular, expansive peak around 2θ = 20° . The DA reaction emerges as a cornerstone in the curing mechanism of PBU within the scope of this research.…”

Section: Resultsmentioning

confidence: 99%

Convolution Neural Networks for Motion Detection with Electrospun Reversibly-Cross-linkable Polymers and Encapsulated Ag Nanowires

Choi,

Shin,

Kim

2023

ACS Appl. Mater. Interfaces

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This paper presents the design, fabrication, and implementation of a novel composite film, a polybutadiene-based urethane (PBU)/AgNW/PBU sensor (PAPS), demonstrating remarkable mechanical stability and precision in motion detection. The sensor capitalizes on the integration of Ag nanowire (AgNW) electrodes into a neutral plane, embedded within a reversibly cross-linkable PBU polymer. The meticulous arrangement confers pore-free and interfaceless sensor formation, resulting in an enhanced mechanical robustness, reproducibility, and long-term reliability. The PBU polymer is subjected to an electrospinning process, followed by sequential Diels–Alder (DA) and retro-DA reactions to produce a planarized encapsulation layer. This pioneering technology, based on electrospinning, allows for more flawless engineering of the neutral plane as compared to conventional film lamination or layer-by-layer spin-coating processes. This encapsulation, matching the thickness of the preformed PBU film, effectively houses the AgNW electrodes. The PAPS outperforms conventional AgNW/PBU sensors (APS) in terms of mechanical stability and bending insensitivity. When affixed to various body parts, the PAPS generates distinctive signal curves, reflecting the specific body part and degree of motion involved. The PAPS sensor’s utility is further magnified by the application of machine learning and deep learning algorithms for signal interpretation. K-means clustering algorithm authenticated the superior reproducibility and consistency of the signals derived from the PAPS over the APS. Deep learning algorithms, including a singular 1D convolutional neural network (1D CNN), long short-term memory (LSTM) network, and dual-layered combinations of 1D CNN + LSTM and LSTM + 1D CNN, were deployed for signal classification. The singular 1D CNN model displayed a classification accuracy exceeding 98%. The PAPS sensor signifies a pivotal development in the field of intelligent motion sensors.

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“…[156] We have recently reported the isocyanate and catalyst free one-pot synthesis of biodegradable NIPU films by polyaddition of cyclic carbonate of polycaprolactone triol with biodegradable/sustainable diamines, hexamethylene diamine/isosorbide diamine and terpene-based linalool diamine to form NIPU films as represented in Scheme 70. [171]…”

Section: Chemistryselectmentioning

confidence: 99%

Catalyzed and Non‐catalyzed Synthetic Approaches to Obtain Isocyanate‐free Polyurethanes

Chelike

Andavan

2023

ChemistrySelect

Self Cite

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By reactions of both catalyzed and non-catalyzed pathway, we attempt to show that the synthetic route of non-isocyanate polyurethanes (NIPU) is developed quite recently. The advancement of sustainable, bio-renewable, impermeable and moisture-insensitive NIPU has started to contribute its role in academia and industry. In case of NIPU formulation, polycondensation of dicarbonate with diamine precursors as well as waste-free polyaddition of multifunctional cyclic carbonates with diamines via ring-opening polymerization. Obviously, since the hydroxyl groups (both primary and secondary hydroxyl group) arisen in NIPU is employed to reveal fairly different attributes compared to trivial polyurethanes (PU). The advantage of NIPU comprises of the role of carbon dioxide and renewable feedstock, while various cyclic carbonates obtained to react with diamine substrates to incorporate desired physicochemical and mechanical properties. Indeed, NIPU are noted to be non-toxic, biodegradable and exhibit remarkable properties. In this review, we account the imperative strategies employed in developing essential sustainable NIPU have been discussed in detail.

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Biodegradable isocyanate-free polyurethane films via a noncatalytic route: facile modified polycaprolactone triol and biobased diamine as precursors

Abstract: Synthesis of isocyanate free polyurethanes was executed via catalyst free condition by polyaddition of biodegradable cyclic carbonate from polycaprolactone triol and sustainable diamines formed from linalool and isosorbide diamine by chemical approach.

Cited by 9 publications

References 58 publications

Sustainable Routed Mxene-Based Aminolyzed PU/PCL Film for Increased Oxidative Stress and a pH-Sensitive Drug Delivery System for Anticancer Therapy

Sustainable Routed Mxene-Based Aminolyzed PU/PCL Film for Increased Oxidative Stress and a pH-Sensitive Drug Delivery System for Anticancer Therapy

Convolution Neural Networks for Motion Detection with Electrospun Reversibly-Cross-linkable Polymers and Encapsulated Ag Nanowires

Catalyzed and Non‐catalyzed Synthetic Approaches to Obtain Isocyanate‐free Polyurethanes

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