Self-healing polymers based on thermally reversible Diels–Alder chemistry

Liu, Ying‐Ling; Chuo, Tsai-Wei

doi:10.1039/c2py20957h

Cited by 560 publications

(438 citation statements)

References 91 publications

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“…1 H NMR (300 MHz, DMSO-d 6 ): δ 6.59 (t, J = 0.9 Hz, 2H, Furan (21.82 mL, 300.0 mmol, 1 equivalent) was added to a solution of maleic anhydride (22.09 g, 225.3 mmol, 0.75 equivalents) in 13 mL ethyl acetate and the reaction mixture was stirred for 24 h at room temperature The obtained white precipitate was filtered off and dried in vacuum to yield mainly the exo-compound as a white solid (65%). 1 H NMR (300 MHz, DMSO-d6): δ 6.59 (t, J = 0.9 Hz, 2H, CH=CH), 5.36 (t, J = 0.9 Hz, 2H, CH-O-CH), 3.32 (s, 2H, CH-CH); 13 In a 25 mL Schlenk flask under an argon atmosphere, methacryloyl chloride (0.15 mL, 1.5 mmol, 1.05 equivalent) was added dropwise to a solution of 2-(2-hydroxyethyl) 3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (0.31 g, 1.5 mmol, 1 equivalent) and triethylamine (0.25 mL, 1.8 mmol, 1.2 equivalent) in 7 mL of dry dichloromethane at 0 °C. The reaction mixture was stirred for 2 h at 0 °C.…”

Section: Synthesis Of Monomer Mima and Blank Linear Polymer Pmentioning

confidence: 99%

“…By using supramolecular polymers, or some dynamic covalent chemistry, one can introduce reversible connections in the polymer structure. In particular, the reversible Diels-Alder chemical reaction of furans with maleimides is widely known [12,13]. This reaction needs no more catalysts and it results in useful secondary products, which leads to enhancing the cross-linking mechanisms at simple conditions such as ambient conditions.…”

Section: Introductionmentioning

confidence: 99%

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RETRACTED: Controlled Light Cross-Linking Technique to Prepare Healable Materials

et al. 2017

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Detection of defects, damages and cracks in structural polymers is very difficult, and even if they are detected, they will be very hard to be repaired. This is because different kinds of stress can reduce the mechanical efficiency of structural and functional thermosetting composite materials and they can damage the polymer matrix, thus reducing the purposed properties. General healing processes use thermal energy "alone" to heal these materials, thus impairing the intended properties of the materials. Therefore, we present a thermal healing ability that can be switched-on and/or -off at desire using illumination by photon energy (visible and ultra violet). By this technique, one can control local heal while keeping the efficiency of the material nearly unchanged. Furan-based cross-linker chemically reacts (forward-and reverse-reaction) with short-chains of maleimide-substituted poly(lauryl methacrylate) to form robust chemical bonds. This permits us to perform local control over thermally induced de-and/or re-cross-linking techniques. One can extend and apply this technique to cover micro-devices, coating-techniques, fine lithography, micro-and nano-fabrication processes, etc. Therefore, the present work developed a suitable technology with structural polymeric material, which has the ability to self-heal cracks (and damages) and recover structural function.

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Section: Synthesis Of Monomer Mima and Blank Linear Polymer Pmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

RETRACTED: Controlled Light Cross-Linking Technique to Prepare Healable Materials

et al. 2017

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“…Reactant 3-(furan-2-ylmethyl)-8-methoxy-3,4-dihydro-2H-benzo[e] [1,3]oxazine (GF) was synthesized according to the literature [33]. Aniline (99.5%), acetic anhydride (98.5%) and hexane were purchased from Merck (Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…The Diels-Alder (DA) reaction, known as (4+2) cycloaddition reaction between diene and dienophile, is one of the most useful reactions in organic [1] and material synthesis [2,3]. DA reaction belongs to the group of 'click' reactions known as almost completely versatile, efficient and selective synthesis [4].…”

Section: Introductionmentioning

confidence: 99%

Characterization and kinetic study of Diels-Alder reaction: Detailed study on N-phenylmaleimide and furan based benzoxazine with potential self-healing application

Štirn¹,

Ručigaj²,

Krajnc³

2016

Express Polym. Lett.

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Abstract. The Diels-Alder reaction between N-phenylmaleimide and benzoxazine bearing furan group was investigated for the purpose of successful appliance of self-healing in benzoxazine polymer networks. The reaction as a function of temperature/time was performed in molten state and in a solution, where also the kinetic study was performed. The Diels-Alder reaction leads to a mixture of two diastereomers: endo presented at lower cyclo-reversion temperature and exo at higher. Therefore, the conversion rates and exo/endo ratio were studied in detail for both systems. For instance, in molten state the Diels-Alder reaction was triggered by the temperature of the melting point at 60°C with exo/endo ratio preferable to the endo adduct. The study of the kinetics in a solution revealed that the Diels-Alder reaction followed typical bimolecular reversible second-order reaction. The activation energies were close to the previous literature data; 48.4 and 51.9 kJ·mol -1 for Diels-Alder reaction, and 91.0 and 102.3 kJ·mol -1 for retro-Diels-Alder reaction, in acetonitrile and chloroform, respectively. The reaction equilibrium in a solution is much more affected by the retro-Diels-Alder reaction than in a molten state. This study shows detailed investigation of DA reaction and provides beneficial knowledge for further use in self-healing polymer networks.

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“…Self-healing is a biological phenomenon that provides a spontaneous recovery of the wound without any external stimuli. In synthetic polymeric system self-healing can be of two types; (i) induced self-healing like pH 34 , light 35 , heat 36 etc. and (ii) non-induced self-healing via formation of ionic interaction 34 , H-bonding 37 , π-π stacking 38 , metal coordination 39 etc.…”

Section: Introductionmentioning

confidence: 99%

A self-healable fluorescence active hydrogel based on ionic block copolymers prepared via ring opening polymerization and xanthate mediated RAFT polymerization

et al. 2018

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Self-healing polymers based on thermally reversible Diels–Alder chemistry

Cited by 560 publications

References 91 publications

RETRACTED: Controlled Light Cross-Linking Technique to Prepare Healable Materials

RETRACTED: Controlled Light Cross-Linking Technique to Prepare Healable Materials

Characterization and kinetic study of Diels-Alder reaction: Detailed study on N-phenylmaleimide and furan based benzoxazine with potential self-healing application

A self-healable fluorescence active hydrogel based on ionic block copolymers prepared via ring opening polymerization and xanthate mediated RAFT polymerization

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