Thermally Remendable Polyurethane Network Cross-Linked via Reversible Diels–Alder Reaction

Platonova, E. O.; Chechenov, Islam; Павлов, А. А.; Solodilov, V. I.; Afanasyev, E. S.; Shapagin, A. V.; Polezhaev, Alexander V.

doi:10.3390/polym13121935

Cited by 10 publications

(8 citation statements)

References 51 publications

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“…The latter change of volume is also associated with a change in the geometry of the individual cells. Simultaneously, the change in the viscoelastic and viscoplastic properties of the PU matrix should be assumed due to the PU matrix cross-linking [ 27 ], and partial hydrolysis [ 28 ]. As a complex material response, the varying degrees of swelling of the PU cell walls material were proposed.…”

Section: Resultsmentioning

confidence: 99%

Effect of Conditioning on PU Foam Matrix Materials Properties

et al. 2021

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This article deals with the characterization of the thermal-induced aging of soft polyurethane (PU) foams. There are studied thermal and mechanical properties by means of thermal analysis, tensile, compression and dynamic mechanical vibration testing. It was found in this study, that the increasing relative humidity of the surrounding atmosphere leads to the initiation of the degradation processes. This is reflected in the observed decreased mechanical stiffness. It is attributed to the plasticization of the PU foams wall material. It is in agreement with the observed increase of the permanent deformation accompanied simultaneously with the decrease of Young’s modulus of elasticity. The latter phenomenon is studied by the novel non-destructive forced oscillations vibration-damping testing, which is confirmed by observed lower mechanical stiffness thus indicating the loss of the elasticity induced by samples conditioning. In parallel, observed decreasing of the matrix hardness is confirming the loss of elastic mechanical performance as well. The effect of conditioning leads to the significant loss of the PU foam’s thermal stability.

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Section: Resultsmentioning

confidence: 99%

Effect of Conditioning on PU Foam Matrix Materials Properties

et al. 2021

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“…Recently, Zheng et al prepared self-healable PU composites based on furan–maleimide DA chemistry by incorporating tetramethylene tetranitramine (HMX) filler to improve the tensile strength (σ) up to 13.47 MPa. Similarly, Polezhaev et al reported a triarm thermally remendable and recyclable PU that exhibited σ up to 26 MPa via DA reaction. Yang et al prepared phase-change composites using the maleimide-terminated PEG-based PU and furan-modified dopamine to endow the significant self-healing and photothermal conversion abilities for energy storage applications.…”

Section: Introductionmentioning

confidence: 92%

Ultrafast Derived Self-Healable, Reprocessable Polyurethane Elastomer Based on Dynamic “Electrophilic Substitution (ES)-Click” Chemistry

et al. 2022

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Conventional self-healable polyurethanes (PUs) based on the furan−maleimide combination take several hours to prepare and require an elevated temperature to endow self-healing characteristics via Diels−Alder (DA) chemistry. In this work, furan end-capped triarm PU prepolymers (FAPUs) were prepared using polycaprolactone triol, 4,4′-methylene bis(phenyl isocyanate) (MDI), and furfuryl alcohol in the presence of a tin(II) catalyst. Cross-linked FAPUs were accomplished within 10 s under ambient conditions after reaction with bis-1,2,4-triazoline-3,5-dione (bis-TAD) via ES-Click chemistry. Structural elucidation of the synthesized prepolymer and ES-cross-linked FAPUs was carried out by 1 H NMR and FTIR analyzes. Differential scanning calorimetric (DSC) analysis revealed that TAD-derived FAPU elastomers were thermoreversible at 110 °C and room temperature via ES-Click chemistry, and the thermoreversibility of FAPUs was confirmed via solution reprocessability. The self-healing behavior of PUs was monitored under an optical microscope, by scanning electron microscopy, and by tensile measurement. Unlike pristine prepolymer with a tensile strength of σ = 0.1 N/mm 2 , TAD-derived FAPU 1 polymer showed a significant tensile strength of σ = 34.68 N/mm 2 with healing efficiency (H σ = 83%) without using any additive. The surface microhardness and depth penetration of FAPUs improved significantly after cross-linking with bis-TAD and retained their properties even after healing. Similarly, the resultant TAD-derived PUs had improved surface hydrophobicity compared to pristine PU prepolymers as supported by AFM analysis. These ES-Click-derived PU polymer materials showed significant mechanical, good self-healing, and hydrophobic characteristics and will be potential materials for advanced coatings, adhesives, and paint applications.

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“…Several approaches were used for the synthesis of CANs using fmDA reaction. The synthesis of highly reprocessable cross-linked polymers may be carried out using monomolecular substrates containing three or more furanic and/or maleimide functional groups [99][100][101]. Depending on the structure and ratio of the monomers, polycondensation by fmDA reaction can lead to branched or cross-linked polymers [102].…”

Section: Synthesis Of Cross-linked Dynamers Using the Fmda "Click" Reactionmentioning

confidence: 99%

Diels–Alder Cycloadditions of Bio-Derived Furans with Maleimides as a Sustainable «Click» Approach towards Molecular, Macromolecular and Hybrid Systems

2021

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This mini-review highlights the recent research trends in designing organic or organic-inorganic hybrid molecular, biomolecular and macromolecular systems employing intermolecular Diels–Alder cycloadditions of biobased, furan-containing substrates and maleimide dienophiles. The furan/maleimide Diels–Alder reaction is a well-known process that may proceed with high efficiency under non-catalytic and solvent-free conditions. Due to the simplicity, 100% atom economy and biobased nature of many furanic substrates, this type of [4+2]-cycloaddition may be recognized as a sustainable “click” approach with high potential for application in many fields, such as fine organic synthesis, bioorganic chemistry, material sciences and smart polymers development.

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Thermally Remendable Polyurethane Network Cross-Linked via Reversible Diels–Alder Reaction

Cited by 10 publications

References 51 publications

Effect of Conditioning on PU Foam Matrix Materials Properties

Effect of Conditioning on PU Foam Matrix Materials Properties

Ultrafast Derived Self-Healable, Reprocessable Polyurethane Elastomer Based on Dynamic “Electrophilic Substitution (ES)-Click” Chemistry

Diels–Alder Cycloadditions of Bio-Derived Furans with Maleimides as a Sustainable «Click» Approach towards Molecular, Macromolecular and Hybrid Systems

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