A new recyclable crosslinked polymer combined polyurethane and epoxy resin

Peng, Yong-jin; He, Xin; Wu, Qiang; Sun, Pingchuan; Wang, Changjun; Liu, Xuezheng

doi:10.1016/j.polymer.2018.06.082

Cited by 27 publications

(10 citation statements)

References 31 publications

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“…One of the most effective healing methods is the incorporation of furan/ maleimide Diels-Alder (DA) adducts into polymer networks because the DA and retro DA (rDA) reactions occur thermoreversibly at high chemoselectivity [3,4]. To date, self-healing epoxy [5][6][7][8][9] and polyurethane [10][11][12][13][14] networks have been extensively synthesized through thermoreversible furan/maleimide DA/ rDA reactions. However, although the reversible bonds generated through the DA reaction have been exclusively utilized as cross-linkages in most previous studies, heat resistance and mechanical performance are deteriorated significantly because of the rapid lowering of cross-linking density caused by the rDA reaction at temperatures higher than 100 °C.…”

Section: Introductionmentioning

confidence: 99%

Self-healing high-performance thermosets utilizing furan/maleimide Diels–Alder, epoxy/amine nucleophilic ring-opening, and maleimide/amine Michael reactions

et al. 2021

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The epoxy/amine nucleophilic ring-opening reaction of furfurylamine (FA) with diglycidyl ether of bisphenol A (DGEBA) at a molar ratio of 1/1 generated a polyaddition oligomer (FADGEBA). Mixtures of FADGEBA, 4,4-bismaleimidodiphenylmethane (BMI), and melamine (ML) at FADGEBA(as a repeating unit)/BMI/ ML molar ratios of 2/4/1, 4/5/1, 6/6/1, and 2/1/0 were prepolymerized at 110 °C and hot-pressed at 110-130 °C to produce cured products (FADGBA-BMI-ML-241, -451, -661, and -210). Fourier transform infrared (FT-IR) spectroscopy revealed the occurrence of the maleimide/amine Michael addition of BMI/ML and the furan/ maleimide Diels-Alder (DA) reaction of FADGEBA/BMI. The onset temperatures of the endothermal retro DA reaction for FADGBA-BMI-MLs were ~ 150 °C. The 5% mass loss temperature of FADGEBA-BMI-ML-241 at 347 °C was significantly higher than those of the other cured products. The flexural strengths and flexural strains at break of FADGBA-BMI-MLs increased in the order of FADGEBA-BMI-ML-241 < FADGEBA-BMI-ML-451 < FADGEBA-BMI-ML-661 < FADGEBA-BMI-ML-210, whereas the flexural moduli decreased in the same order. All cured products showed healing properties when hot-pressed at 160 °C/5 MPa. The healing efficiencies on flexural strength were 57-82%.

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Section: Introductionmentioning

confidence: 99%

Self-healing high-performance thermosets utilizing furan/maleimide Diels–Alder, epoxy/amine nucleophilic ring-opening, and maleimide/amine Michael reactions

et al. 2021

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“…DRC involves breaking reversible covalent cross‐links under stimulus, leading to branched and linear chains, and reforming covalent cross‐links upon stimulus removal. Examples of DRC include the Diels–Alder reaction and alkoxyamine chemistry . AEC involves bond exchange, maintaining the number of cross‐links during rearrangement, leaving the network malleable at sufficient exchange rate.…”

Section: Introductionmentioning

confidence: 99%

Reprocessable Polymer Networks Designed with Hydroxyurethane Dynamic Cross‐links: Effect of Backbone Structure on Network Morphology, Phase Segregation, and Property Recovery

Chen

Wei

et al. 2019

Macro Chemistry & Physics

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Polybutadiene (PB), poly(tetramethylene oxide) (PTMO), and polydimethylsiloxane (PDMS) networks are synthesized using relatively low wt% of dynamic hydroxyurethane cross‐links, and recovery of cross‐link density, network morphology, and properties are investigated as a function of reprocessing. PB and PTMO networks exhibit full recovery of rubbery plateau modulus, and thus cross‐link density, and tensile properties after multiple melt‐state recycling steps. PDMS networks exhibit a small loss in rubbery plateau modulus with reprocessing. Small‐angle X‐ray scattering reveals nanophase separation in PB and PDMS networks. Although PTMO networks are not nanophase separated, cold crystallization is observed, with crystallinity increasing after reprocessing because of chain alignment. This work establishes the effective use of hydroxyurethane cross‐links toward full property recovery in different networks and provides insights on the design of reprocessable networks with distinctive morphology and sustainability.

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“…Recently, introducing dynamic covalent bonds and dynamic noncovalent bonds into CCPUs molecular chain can be used to realize reprocessing function, such as oxime-urethane structure, [11] hydrogen bonds, [12] dynamic ionic bonds, [13,14] disulfide, [15,16] diselenide, [17,18] imine, [19] boronic ester bonds, [20] and Diels-Alder (DA). [21,22] Among them, oxime-urethane structure consisting of a carbamate group (-NH-COO-) and an imine bond (C═N), is usually prepared through the reaction between oxime groups and isocyanate groups. The oxime-urethane structure can be easily split into oxime and isocyanate groups because of the strong electric-absorbing effect of C═N.…”

Section: Doi: 101002/marc202100781mentioning

confidence: 99%

Oxime–Urethane Structure‐Based Dynamically Crosslinked Polyurethane with Robust Reprocessing Properties

Yuan

Jiang

et al. 2022

Macromol. Rapid Commun.

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Crosslinked polyurethane with excellent mechanical property, solvent resistance, and transparency has become one of the most widely used materials. However, the presence of chemical crosslinks makes it difficult to be reprocessed once molded, which largely restricts its recycling and reusing, resulting in the serious waste problems. Therefore, it is of great significance to prepare a new type of crosslinked polyurethane with reprocessing function. In this work, a novel reprocessable polyurethane (DOPU) based on reversible dibutanone oxime-carbamate bonds is facilely prepared. The gel fraction of DOPUs is all higher than 95%, endowing it with excellent solvent resistance. Meanwhile, the visible light transmittance of DOPUs can reach up to 97.48%. After four thermal recycles, the tensile strength and elongation at break of recycled DOPUs can still remain at 3.21 MPa and 219.09%, respectively. Importantly, the synthesized DOPUs exhibit excellent elastic shape memory and permanent shape reconstruction properties under thermal stimulation. The dibutanone oxime-carbamate bonds can also be degraded under UV irradiation, making this material easily degradable. Hence, this material has potential applications in coatings, elastomers, and some other fields.

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A new recyclable crosslinked polymer combined polyurethane and epoxy resin

Cited by 27 publications

References 31 publications

Self-healing high-performance thermosets utilizing furan/maleimide Diels–Alder, epoxy/amine nucleophilic ring-opening, and maleimide/amine Michael reactions

Self-healing high-performance thermosets utilizing furan/maleimide Diels–Alder, epoxy/amine nucleophilic ring-opening, and maleimide/amine Michael reactions

Reprocessable Polymer Networks Designed with Hydroxyurethane Dynamic Cross‐links: Effect of Backbone Structure on Network Morphology, Phase Segregation, and Property Recovery

Oxime–Urethane Structure‐Based Dynamically Crosslinked Polyurethane with Robust Reprocessing Properties

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