The effect of electron density in furan pendant group on thermal-reversible Diels–Alder reaction based self-healing properties of polymethacrylate derivatives

Byun, Keum-Seob; Choi, Won Jae; Lee, Ha-Young; Sim, Min‐Ji; Cha, Sang‐Ho; Lee, Jong-Chan

doi:10.1039/c8ra07268j

Cited by 8 publications

(5 citation statements)

References 35 publications

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“…Polymers 2020, 12, x FOR PEER REVIEW 7 of 14 the self-healable properties of the nanocomposites are described, the Diels-Alder reaction between the furan-functional group of FEEMA64 and the maleimide group of BM is characterized using FT-IR analyses of the FEEMA64 polymer film. As shown in Figure 3a, the characteristic peaks at 1581 and 1569 cm −1 , which originated from the furan double bond, decreased after mixing FEEMA64 polymer and BM, showing that the Diels-Alder reaction occurred in the FEEMA64 polymer film [51]. Furthermore, in the case of FEEMA64_mGO0.030 wt%, the characteristic peaks attributed to the furan double bond are reduced compared to the polymer film; this was additionally confirmed via the peak at 1014 cm −1 , attributed to furan ring breathing [52].…”

Section: Characterization Of Feema64 Nanocompositesmentioning

confidence: 93%

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Lee

Cha

2020

Polymers

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In this paper, a self-healable nanocomposite based on the Diels-Alder reaction is developed. A graphene-based nanofiller is introduced to improve the self-healing efficiency, as well as the mechanical properties of the nanocomposite. Graphene oxide (GO) is modified with maleimide functional groups, and the maleimide-modified GO (mGO) enhanced the compatibility of the polymer matrix and nanofiller. The tensile strength of the nanocomposite containing 0.030 wt% mGO is improved by 172%, compared to that of a polymer film incorporating both furan-functionalized polymer and bismaleimide without any nanofiller. Moreover, maleimide groups of the surface on mGO participate in the Diels-Alder reaction, which improves the self-healing efficiency. The mechanical and self-healing properties are significantly improved by using a small amount of mGO.

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Section: Characterization Of Feema64 Nanocompositesmentioning

confidence: 93%

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Lee

Cha

2020

Polymers

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“…125 A recent study suggests that more efficient self-healing was observed when the furan group is substituted with electron rich moieties. 126 Correspondingly, other monomers of similar chemical makeup should be investigated.…”

Section: Self-healing Resinsmentioning

confidence: 99%

Multifunctionality in Epoxy Resins

2019

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Epoxy resin will continue to be in the forefront of many thermoset applications due to its versatile properties. However, with advancement in manufacturing, changing societal outlook for the chemical industries and emerging technologies that disrupt conventional approaches to thermoset fabrication, there is a need for a multifunctional epoxy resin that is able to adapt to newer and robust requirements. Epoxy resins that behave both like a thermoplastic and a thermoset resin with better properties are now the norm in research and development. In this paper, we viewed multifunctionality in epoxy resins in terms of other desirable properties such as its toughness and flexibility, rapid curing potential, self-healing ability, reprocessability and recyclability, high temperature stability and conductivity, which other authors failed to recognize. These aspects, when considered in the synthesis and formulation of epoxy resins will be a radical advance for thermosetting polymers, with a lot of applications. Therefore, we present an overview of the recent finding as to pave the way for varied approaches towards multifunctional epoxy resins.

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“…[57] Entry RH OMO ah andful of other studies describe the use of furoic acid esters,namely in macromolecular applications,i nc ontrast to the abundant literature on the related furfuryl alcohol esters; this is again testament to the relative ease of cycloaddition in the latter systems. [74][75][76][77] At the other end of the spectrum, substituents with positive mesomeric effects (-OR, OCOR, -NR 2 ,N HCOR, etc. )l ead to the most notable rate enhancements,a s exemplified in Scheme 5; increased reactivity due to inductive effects is much less frequently observed and typically involves rather exotic functional groups (e.g.-BF 3 K).…”

Section: Methodsmentioning

confidence: 99%

“…Under neat conditions, the reaction rate benefits from the high concentration effect, while activation by hydrogen‐bond formation is likely again involved when the reaction is run on water. Notably, only a handful of other studies describe the use of furoic acid esters, namely in macromolecular applications, in contrast to the abundant literature on the related furfuryl alcohol esters; this is again testament to the relative ease of cycloaddition in the latter systems [74–77] …”

Section: Kineticsmentioning

confidence: 99%

The Interplay between Kinetics and Thermodynamics in Furan Diels–Alder Chemistry for Sustainable Chemicals Production

et al. 2022

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Biomass‐derived furanic platform molecules have emerged as promising building blocks for renewable chemicals and functional materials. To this aim, the Diels–Alder (DA) cycloaddition stands out as a versatile strategy to convert these renewable resources in highly atom‐efficient ways. Despite nearly a century worth of examples of furan DA chemistry, clear structure–reactivity–stability relationships are still to be established. Detailed understanding of the intricate interplay between kinetics and thermodynamics in these very particular [4+2] cycloadditions is essential to push further development and truly expand the scope beyond the ubiquitous addend combinations of electron‐rich furans and electron‐deficient olefins. Herein, we provide pertinent examples of DA chemistry, taken from various fields, to highlight trends, establish correlations and answer open questions in the field with the aim to support future efforts in the sustainable chemicals and materials production.

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The effect of electron density in furan pendant group on thermal-reversible Diels–Alder reaction based self-healing properties of polymethacrylate derivatives

Abstract: Herein, we discuss the effect of electron density in a furan pendant group on the thermally reversible Diels–Alder (DA) reaction based self-healing efficiency in polymethacrylate derivatives.

Cited by 8 publications

References 35 publications

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Multifunctionality in Epoxy Resins

The Interplay between Kinetics and Thermodynamics in Furan Diels–Alder Chemistry for Sustainable Chemicals Production

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