Aromatic diselenide crosslinkers to enhance the reprocessability and self-healing of polyurethane thermosets

An, Xiaowei; Aguirresarobe, Robert H.; Irusta, L.; Ruipérez, Fernando; Matxain, Jon M.; Pan, Xiangqiang; Aramburu, Nora; Mecerreyes, David; Sardón, Haritz; Zhu, Jian

doi:10.1039/c7py00448f

Cited by 109 publications

(84 citation statements)

References 29 publications

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“…Besides, after the same healing process, the tensile strength and ultimate elongation of PTPU‐T restore to 29.3% and 24.5% of the original values, respectively, also both lower than that of A‐LP23‐T (61.2% and 29.7%). The healing efficiencies of PTPU‐I and PTPU‐T, without dynamic disulfide bonds, may be attributed to the contribution of the hydrogen bonds interaction . The higher healing efficiencies of A‐LP23‐I and A‐LP23‐T are inseparable from the effect of the disulfide metathesis reaction.…”

Section: Resultsmentioning

confidence: 99%

Aromatic amine‐terminated polysulfide oligomer: Synthesis and application in self‐healable polyurea

Gao

Zuo

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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The dynamic chemistry of disulfide bonds has emerged as one of the most powerful tools used for the fabrication of organic compounds and self‐healing materials. In this article, a novel aromatic amine‐terminated polysulfide oligomer is first synthesized from thiol‐terminated polysulfide oligomer and bis(4‐aminophenyl) disulfide via disulfide metathesis mechanism. The resulting oligomer is confirmed by FTIR and 1H NMR spectra and then successfully applied in constructing self‐healable polyurea material (A‐LP23‐I), which combines the advantages of higher strength of polyureas and excellent self‐healing ability of polysulfide‐based materials. After subjecting to a temperature of 75 °C for 48 h, both the tensile strength and ultimate elongation of A‐LP23‐I restore to more than 90% of the original values (3.32 MPa and 396%). This study demonstrates a novel strategy for synthesizing aromatic amine‐terminated oligomer. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1460–1466

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Section: Resultsmentioning

confidence: 99%

Aromatic amine‐terminated polysulfide oligomer: Synthesis and application in self‐healable polyurea

Gao

Zuo

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…In comparison with disulfide bonds, diselenide bonds are more dynamic due to a lower bond energy. Thereby, PU networks with aromatic diselenide exhibit the greater ability to be processed . What is more, Cheng's group reported that the hindered urea bonds showed a dynamic nature under ambient/catalyst‐free conditions .…”

Section: Introductionmentioning

confidence: 99%

Reconfigurable and Reprocessable Thermoset Shape Memory Polymer with Synergetic Triple Dynamic Covalent Bonds

Wang

Pan

Zheng

et al. 2018

Macromol. Rapid Commun.

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Degradable shape memory polymers (SMPs), especially for polyurethane-based SMPs, have shown great potential for biomedical applications. How to reasonably fabricate SMPs with the ideal combination of degradability, shape reconfigurability, and reprocessability is a critical issue and remains a challenge for medical disposable materials. Herein, a shape memory poly(urethane-urea) with synergetic triple dynamic covalent bonds is reported via embedding polycaprolactone unit into poly(urethane-urea) with the hindered urea dynamic bond. The single polymer network is biodegradable, thermadapt, and reprocessable, without sacrificing the outstanding shape memory performance. Such a shape memory network with plasticity and reprocessability is expected to have significant and positive impact on the medical device industry.

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“…In contrast, taking the reversible nature of dynamic covalent bond to fabricate self‐healing materials becomes the intriguing challenge of the scientists and engineers. Currently known self‐healing materials containing disulfide bonds are regarded as one of the most promising alternatives due to the reversible nature, high versatility, and low price . Although many significant results have been reported, some of these materials needed high temperatures and even external pressures to be healed and remolded .…”

Section: Introductionmentioning

confidence: 99%

“…This indicates that diselenide bonds can be more dynamic, and their exchange reactions are probably occurred under much milder conditions. In fact, diselenide bonds have been incorporated into PU materials that can be self‐healed under light or heat . Ji et al .…”

Section: Introductionmentioning

confidence: 99%

“…proposed the introduction of aromatic diselenide compounds to prepare healable PU in which the exchange of diselenide bonds can be occurred at ambient temperature, even in the dark condition . Likewise, the dynamic metathesis of diselenide bonds also increased with the increase of temperature, resulting in an improved self‐healing and reprocessing performances . As inspired by this property, we envision that incorporating the diselenide into the segmented PU chains, the design of novel PU material possessing both shape memory and healable properties is implementable.…”

Section: Introductionmentioning

confidence: 99%

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Thermal induced shape‐memory and self‐healing of segmented polyurethane containing diselenide bonds

Jin

Pan

et al. 2018

J of Applied Polymer Sci

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Herein, we synthesized a series of polyurethane copolymers (PUs) with poly(1,4-butylene adipate) glycol as soft segment and 2,4-toluene diisocyanate as well as extenders including 1,4-butanediol and di(1-hydroxyethylene) diselenide as hard segment. The chemical structure, thermal property, crystallization behavior, shape memory, and self-healing performances of the PUs were systematically characterized by a series of experiments. It was found that the PU2 containing a higher diselenide component (33 mol %) exhibited both shape memory and self-healing behaviors under a moderate temperature (57 8C). Meanwhile, the PUs showed a good repeatability of shape memory function, and their fixity and recovery ratios were all above 90%. Additionally, the dynamic exchangeable feature of diselenide bonding endues the PUs chains with an acceptable reprocessability and self-healing performances, and the PU2 sample could be healed for five times by thermal treatment with the healing efficiencies above 70%. This work provides a heuristic perspective for the development of shape memory and self-healing materials. V C 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46326.

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Aromatic diselenide crosslinkers to enhance the reprocessability and self-healing of polyurethane thermosets

Abstract: We explore the utilization of aromatic diselenides as new low temperature exchangeable monomers for their utilization in thermosets.

Cited by 109 publications

References 29 publications

Aromatic amine‐terminated polysulfide oligomer: Synthesis and application in self‐healable polyurea

Aromatic amine‐terminated polysulfide oligomer: Synthesis and application in self‐healable polyurea

Reconfigurable and Reprocessable Thermoset Shape Memory Polymer with Synergetic Triple Dynamic Covalent Bonds

Thermal induced shape‐memory and self‐healing of segmented polyurethane containing diselenide bonds

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