Thermo-reversible self-healing in a fluorous crosslinked copolymer

Padhan, Anil K.; Mandal, Debaprasad

doi:10.1039/c8py00471d

Cited by 28 publications

(27 citation statements)

References 58 publications

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“…This is quite similar to the reported observation on several methacrylate, furan/maleimide systems for DA adduct formation . The retro‐DA product shows the appearance of CO stretching and furan peaks at 1722 and 1497 cm −1 , respectively.…”

Section: Resultssupporting

confidence: 90%

“…Self‐healing polymers have interesting characteristics to self‐repair damages inside the polymer matrix and can recover the materials' original shape and properties. There have been several approaches to achieve self‐healing characteristics in the polymer . Among them, the approach via DA “Click Reaction” is very important, as this is thermally reversible in nature leading to the multiple time of healing .…”

Section: Introductionmentioning

confidence: 99%

“…Among them, the approach via DA “Click Reaction” is very important, as this is thermally reversible in nature leading to the multiple time of healing . One of the excellent examples of reversible crosslinking reaction is between a furan and a maleimide, that is, DA reaction . FMA is an interesting monomer due to its pendent reactive furfuryl group, which can be used as a diene for DA reaction to prepare self‐healing polymer.…”

Section: Introductionmentioning

confidence: 99%

“…There have been several approaches to achieve self-healing characteristics in the polymer. [36][37][38][39] Among them, the approach via DA "Click Reaction" is very important, as this is thermally reversible in nature leading to the multiple time of healing. 40,41 One of the excellent examples of reversible crosslinking reaction is between a furan and a maleimide, that is, DA reaction.…”

Section: Introductionmentioning

confidence: 99%

“…40,41 One of the excellent examples of reversible crosslinking reaction is between a furan and a maleimide, that is, DA reaction. 29,[38][39][40][41] FMA is an interesting monomer due to its pendent reactive furfuryl group, which can be used as a diene for DA reaction to prepare self-healing polymer. However, the healing nature of the polymers requires external factors like heating or use of an external maleimide-based crosslinker involving bond-breaking and making process.…”

Section: Introductionmentioning

confidence: 99%

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Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

Sahu

Bhowmick

2019

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

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Motivated by the growing demand for greener and sustainable polymer systems, self‐healing elastomers were prepared by emulsion polymerization of terpene and furfural‐based monomers. Both the method and the monomers were green and sustainable. The synthesized copolymers showed molecular weights between 59,080 and 84,210 Da and glass‐transition temperature (Tg) between −25 and −40 °C, implying rubbery properties. A set of one‐dimensional (1D) and two‐dimensional (2D) NMR spectroscopy supported the formation of the copolymer and nuclear spin–spin coupling in the copolymer. Reactivity ratios were determined by conventional linear method. A thermoreversible network was achieved for the first time by reacting the furan‐based polymer with bismaleimide (BM) as a crosslinker, via a Diels−Alder (DA) coupling reaction. The reversible nature of the polymer network was evidenced from infrared and NMR spectroscopy. The thermoreversible character of the DA crosslinked adduct was confirmed by applying retro‐DA reaction (observed in differential scanning calorimeter [DSC] analysis) and mechanical recovery was verified by repeated heating and cooling cycles. The network polymers displayed excellent self‐healing ability, triggered by heating at 130 °C for 4–12 h, when their scratched surface was screened by microscopic visualization. The healing efficiency of the crosslinked DA‐adduct was calculated as 78%, using atomic force microscopy. This work provides a green and efficient approach to prepare new green and functional materials. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 738–751

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

Sahu

Bhowmick

2019

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

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Self‐Healing of Elastomers

2021

Rubber to Rubber Adhesion

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Highly Transparent and Colorless Self‐Healing Polyacrylate Coatings Based on Diels–Alder Chemistry

Fortunato

Tatsi

Rigatelli

et al. 2020

Macro Materials & Eng

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the development of approaches based on disulfide bond exchange, [3] alkoxyamine dissociation, [4] thiol-Michael reaction, [5] Alder-ene addition, [6] and bulky urea bonds, [7] the most widely reported systems are based on the well-established Diels-Alder (DA) cycloaddition. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] DA is a click-type addition reaction between a dienophile and a diene, typically a maleimide and a furan. The design of a polymer network where crosslinks are constituted by DA adducts would result in the ability to cleave the crosslinks at mildto-high temperature through a retro Diels-Alder process (r-DA), while enabling their reformation upon cooling through the direct DA reaction. Therefore, the r-DA/ DA sequence can be exploited to repair cracks or to remold the crosslinked material. [24] The concept, firstly described in a patent [25] and then in the milestone work of Wudl [26] has been exploited for the dynamic crosslinking of different polymer matrices like epoxies, [27,28] elastomers, [29,30] polyesters, [31,32] and polyketones. [33,34] A straightforward strategy to design DA crosslinked acrylates is based on the combination of linear copolymers of furfuryl methacrylates (FMAs) with difunctional maleimide linkers. [8][9][10]12,16,20] The reported systems are typically characterized by high healing efficiency. However, they lack in transparency and usually exhibit a yellow-to-orange color, predominantly due to the use of aromatic bismaleimide linkers. This feature factually forbids the utilization of DA-based acrylates for optical applications, where high levels of transmittance in the visible wavelength range are inevitably required.To bridge this gap, a straightforward strategy to prepare colorless and transparent thermoresponsive acrylates based on the DA chemistry is proposed in this work. Furan functional polyacrylates were synthetized via free radical polymerization of FMA with methacrylates bearing different aliphatic groups. Two aliphatic bismaleimides, with different chain length, were synthesized starting from the respective diamines. The obtained linear copolymers containing furan moieties were combined with the bismaleimides in solvent, and colorless, high-transmittance, crosslinked coatings were obtained. The thermal reversibility of the DA-coatings was assessed by means of differential scanning calorimetry (DSC) and solubility experiments. After assessing the self-healing ability of the acrylicbased polymeric materials, the effect of network structure (i.e.,

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Thermo-reversible self-healing in a fluorous crosslinked copolymer

Abstract: Self-healing in a fluorous copolymer material enhances its safety index and extends its working lifetime.

Cited by 28 publications

References 58 publications

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

Self‐Healing of Elastomers

Highly Transparent and Colorless Self‐Healing Polyacrylate Coatings Based on Diels–Alder Chemistry

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