Vanillin-based degradable epoxy vitrimers: Reprocessability and mechanical properties study

Yu, Qingqing; Peng, Xionghou; Wang, Yuli; Geng, Hongwei; Xu, Anchang; Zhang, Xi; Xu, Weilin; Ye, Dezhan

doi:10.1016/j.eurpolymj.2019.04.053

Cited by 123 publications

(100 citation statements)

References 51 publications

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“…E a was found to be 53.3 kJ/mol, which was lower than that of the resin systems published recently. [33,35,36] This lower activation energy suggested that the aromatic Weight loss by TGA (%)…”

Section: Dynamic Propertiesmentioning

confidence: 99%

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Welding and reprocessing of disulfide‐containing thermoset epoxy resin exhibiting behavior reminiscent of a thermoplastic

Memon

Wei

2020

J of Applied Polymer Sci

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Thermoset resins generally lack the ability to be welded or reprocessed like thermoplastics because of their cross‐links. Increasing use of fiber‐reinforced composites in large structures, such as rail and aircraft parts, as well as wind blades, calls for better ways to repair damages and be compliant with recycling and environmental regulations. In this article, an epoxy resin containing disulfide bonds was prepared and characterized by Fourier transform infrared, 1H‐NMR, and 13C‐NMR. The dynamic nature of the disulfide bonds allowed the cured epoxy resin to be welded like thermoplastics, and the welded joints had strength that matched the resin's cohesive strength. It could also be reprocessed with 90% tensile strength retention after three reprocessing cycles, allowing the parts to be repaired instead of being replaced. In addition, the cured resin was chemically degradable in a thiol‐based solvent, allowing it to be recycled in closed‐loop processes. Moreover, the cured epoxy resin showed a glass transition temperature of 116°C, demonstrating its potential for advanced composite applications.

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Section: Dynamic Propertiesmentioning

confidence: 99%

“…The protons belonging to epoxy rings were located at 2.7 and 2.8 ppm ( CH 2 in oxirane), 3.32 ppm ( CH in oxirane), 3.83 and 4.33 ppm ( O CH 2 ). [35,36] The disappearance of the peak at 3.47 ppm (Ar-OH) in the 1 H-NMR spectrum of BGPDS signified the full epoxidation of BHPDS.…”

Section: Synthesis and Curing Of Disulfidecontaining Epoxy Resinmentioning

confidence: 99%

Welding and reprocessing of disulfide‐containing thermoset epoxy resin exhibiting behavior reminiscent of a thermoplastic

Memon

Wei

2020

J of Applied Polymer Sci

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“…In the past couple of years, others have adapted the original epoxy-alcohol vitrimers to bio-based systems with higher amounts of crosslinks by incorporating multifunctional epoxies with other multifunctional alcohol or anhydride [216][217][218][219] or amine crosslinking groups. [220][221][222][223][224] Overall, these systems resulted in reversible, recyclable, high-T g dynamic polymer networks synthesized from renewable resources with the goal of increasing the operational windows of bio-based systems. 204 Transamination.…”

Section: Permanent Dynamic Network or Vitrimersmentioning

confidence: 99%

“…Although similar to transesterification, transamination reactions include transamination of vinylogous urethanes, 225,226 diketoenamines 207,208 and imines. [220][221][222][227][228][229][230] Typically considered an associative dynamic reaction (Scheme 3), free primary amines attack either vinylogous urethane ⊎-carbons, diketoenamines or imine functional groups in a mechanism similar to that of transesterification. A wide range of amine hardeners appear in the literature producing a library similar to traditional epoxyamine systems, where concentration (network density) and chemical composition (energetics of bond exchange and entropy of polymer chains) affect T g and T v .…”

Section: Permanent Dynamic Network or Vitrimersmentioning

confidence: 99%

Stimuli‐responsive mechanical properties in polymer glasses: challenges and opportunities for defense applications

Dennis

Savage

Mrozek

et al. 2020

Polymer International

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The potential utility that responsive glasses provide in the areas of aeronautics, protection and unmanned systems is reviewed in this article. The article focuses on two broad classes of stimuli, photo and thermal, to better illustrate the challenges and convey some of the potential in developing these materials for the often extreme operational environments of defense applications. Three response mechanisms are outlined to provide a range of mechanical behaviors on demand: (i) shape-changing functionalities which locally yield or soften the material to stimulate chain mobility; (ii) bond forming (or breaking) chemistries which increase (or decrease) the stiffness of the material; and (iii) energy absorbing groups which convert the incoming stimuli into a spatially controlled heating and result in a designed softening of the material. Overall, continuing to develop responsive polymer glasses that respond rapidly and efficiently under low energy inputs will be critical for future defense applications.

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“…Due to its aromatic structure, vanillin could replace widely used petro-based aromatic monomers [13]. Vanillin polymers exhibit re-processability and biodegradability under acid solution [14], as well as biodegradability in soil [15]. Recently, vanillin has been used to synthesize high-performance flame-retardant epoxy resins containing phosphorus [16].…”

Section: Introductionmentioning

confidence: 99%

Vanillin Acrylate-Based Resins for Optical 3D Printing

et al. 2020

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The investigation of biobased systems as photocurable resins for optical 3D printing has attracted great attention in recent years; therefore, novel vanillin acrylate-based resins were designed and investigated. Cross-linked polymers were prepared by radical photopolymerization of vanillin derivatives (vanillin dimethacrylate and vanillin diacrylate) using ethyl(2,4,6-trimethylbenzoyl)phenylphosphinate as photoinitiator. The changes of rheological properties were examined during the curing with ultraviolet/visible irradiation to detect the influences of solvent, photoinitiator, and vanillin derivative on cross-linking rate and network formation. Vanillin diacrylate-based polymers had higher values of yield of insoluble fraction, thermal stability, and better mechanical properties in comparison to vanillin dimethacrylate-based polymers. Moreover, the vanillin diacrylate polymer film showed a significant antimicrobial effect, only a bit weaker than that of chitosan film. Thermal and mechanical properties of vanillin acrylate-based polymers were comparable with those of commercial petroleum-derived materials used in optical 3D printing. Also, vanillin diacrylate proved to be well-suited for optical printing as was demonstrated by employing direct laser writing 3D lithography and microtransfer molding techniques.

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Vanillin-based degradable epoxy vitrimers: Reprocessability and mechanical properties study

Cited by 123 publications

References 51 publications

Welding and reprocessing of disulfide‐containing thermoset epoxy resin exhibiting behavior reminiscent of a thermoplastic

Welding and reprocessing of disulfide‐containing thermoset epoxy resin exhibiting behavior reminiscent of a thermoplastic

Stimuli‐responsive mechanical properties in polymer glasses: challenges and opportunities for defense applications

Vanillin Acrylate-Based Resins for Optical 3D Printing

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