Epoxy‐amine based thermoresponsive networks designed by Diels–Alder reactions

Marref, Mohamed; Mignard, Nathalie; Jegat, Corinne; Taha, Mohamed; Belbachir, Mohammed; Méghabar, Rachid

doi:10.1002/pi.4287

Cited by 38 publications

(39 citation statements)

References 57 publications

(81 reference statements)

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“…22 Although not shown, similar results were obtained in the case of using Jeffamine V R ED 2003. Figure 2 shows the 1 H NMR spectra of Jeffamine V R , BMI I and BMI II.…”

supporting

confidence: 86%

“…22,23 Then, chain extension was performed by a Michael addition reaction between the obtained bismaleimides and the amine end groups of additional Jeffamine V R ED, resulting in bismaleimides of higher molecular weight. 24 This three-step procedure is depicted in Scheme 1.…”

Section: Bismaleimide Synthesismentioning

confidence: 99%

“…18,20,21 The modification of Jeffamines V R with maleic anhydride was studied for the design of DA networks based on epoxy-amine type oligomers bearing furan groups. 22 However, to the best of our knowledge there is no record of the use of Jeffamine V R -based bismaleimides as cross-linking agents in DA reaction for hydrogel synthesis.…”

mentioning

confidence: 98%

“…2(b,c)]. 22 The conversion of the amines was calculated by 1 H NMR spectroscopy by comparing the proton integration of the maleimide protons with that of the protons of the Jeffamine V R backbone, resulting in 71 and 51% for BMI II ED 900 and BMI II ED 2003, respectively.…”

mentioning

confidence: 99%

“…The average functionality of the samples was determined by 1 H NMR using an equation reported in the literature (eq 2), 22 by comparing the integration values of the proton signals corresponding to the maleamic acid and the maleimide ring:…”

mentioning

confidence: 99%

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Hydrogel synthesis by aqueous Diels‐Alder reaction between furan modified methacrylate and polyetheramine‐based bismaleimides

García‐Astrain

Algar

Gandini

et al. 2014

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

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A simple method for preparing cross-linked hydrogels in an aqueous medium is investigated using Diels-Alder (DA) "click" reaction, without employing a catalyst. A polymeric diene is first synthesized by the functionalization of poly(2-aminoethyl methacrylate) hydrochloride with furfural. Suited bisdienophiles are prepared by modification of Jeffamine V R ED of different molecular weights with maleic anhydride. Both precursors of the DA coupling are thoroughly characterized before their reactions. The ensuing hydrogels are analyzed in terms of their microstructure, swelling, and rheological behavior, as a function of the reaction conditions. The influence of the molecular weight of the cross-linker and the furan-to-maleimide ratio on the final properties of the hydrogels were also investigated.

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“…22 Although not shown, similar results were obtained in the case of using Jeffamine V R ED 2003. Figure 2 shows the 1 H NMR spectra of Jeffamine V R , BMI I and BMI II.…”

supporting

confidence: 86%

Section: Bismaleimide Synthesismentioning

confidence: 99%

mentioning

confidence: 98%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Hydrogel synthesis by aqueous Diels‐Alder reaction between furan modified methacrylate and polyetheramine‐based bismaleimides

García‐Astrain

Algar

Gandini

et al. 2014

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

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Relationship on structure and properties of polyurethane modified Diels–Alder addition polymer

Liu

et al. 2018

J of Applied Polymer Sci

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A series of linear and crosslinked polyurethane modified materials were prepared by Diels-Alder cycloaddition reaction. Based on raw materials, some novel equations were designed and effects of equation parameters on the mechanical properties of modified material were explored. It was demonstrated that tensile strength of modified materials and elongation at break were changed from 3.68 to 18.71 MPa, 200 to 866%, respectively. In addition, the optimal reaction temperature of retro-Diels-Alder (r-DA) reaction was determined by differential scanning calorimeter (DSC). Gel permeation chromatography (GPC) and tensile experiments were used to characterize the properties of repolymerized material after degradation. The results indicated the optimal temperature of r-DA for linear and crosslinked polyurethane modified materials is 127 and 150 C. Moreover, after decomposed, the product was slowly repolymerized at 60 C, and can more effectively restore material strength under the action of the solvent to achieve self-healing effect.

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Self‐healing semi‐IPN materials from epoxy resin by solvent‐free furan–maleimide Diels–Alder polymerization

Zolghadr

Shakeri

Zohuriaan‐Mehr³

et al. 2019

J of Applied Polymer Sci

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Novel self‐healing Diels–Alder (DA) polymer and the corresponding semi‐interpenetrated polymer networks (semi‐IPNs) were synthesized and characterized. Initially, a furan‐functionalized resin (FFR) was synthesized through the ring‐opening reaction of a conventional epoxy resin [diglycidyl ether bisphenol A (DGEBA)] with furfuryl alcohol as a bio‐based compound. Subsequently, semi‐IPNs with different compositions were obtained through the blending of DGEBA, FFR, 4,4′‐diaminodiphenylmethane, and 1,1′‐(methylenedi‐1,4‐phenylene) bismaleimide in the molten state by following a predetermined time–temperature program. Fourier transform infrared and nuclear magnetic resonance analyses confirmed the successful synthesis of the materials. Thermoreversibility via retro‐DA (rDA) reaction was evidenced by differential scanning calorimetry (DSC) and sol–gel transition tests. Repeated DSC cycle was successfully performed thrice on the DA polyadduct which corroborated repeatability of the DA/rDA association/dissociation. Self‐healing and mechanical properties were preliminarily evaluated by scanning electronic microscopy and flexural testing analyses, respectively. The self‐healing efficiencies were around 80 and 95% for semi‐IPN and DA polyadduct, respectively, based on flexural strength. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48015.

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Epoxy‐amine based thermoresponsive networks designed by Diels–Alder reactions

Cited by 38 publications

References 57 publications

Hydrogel synthesis by aqueous Diels‐Alder reaction between furan modified methacrylate and polyetheramine‐based bismaleimides

Hydrogel synthesis by aqueous Diels‐Alder reaction between furan modified methacrylate and polyetheramine‐based bismaleimides

Relationship on structure and properties of polyurethane modified Diels–Alder addition polymer

Self‐healing semi‐IPN materials from epoxy resin by solvent‐free furan–maleimide Diels–Alder polymerization

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