Simultaneous Recovery of Matrix and Fiber in Carbon Reinforced Composites through a Diels–Alder Solvolysis Process

Fortunato, Giovanni; Anghileri, Luca; Griffini, Gianmarco; Turri, Stefano

doi:10.3390/polym11061007

Cited by 31 publications

(27 citation statements)

References 56 publications

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“…Therefore, the r‐DA/DA sequence can be exploited to repair cracks or to remold the crosslinked material . The concept, firstly described in a patent and then in the milestone work of Wudl has been exploited for the dynamic crosslinking of different polymer matrices like epoxies, elastomers, polyesters, and polyketones …”

Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 99%

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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Section: Thermal Properties Of Copolymers After Crosslinking With C6 mentioning

confidence: 99%

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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“…[10][11][12] The introduction of DA adduct through the reaction between bismaleimide and furan groups has also been extensively explored. [13][14][15] However, according to different authors, the Michael's addition that may happen between bismaleimide and amines used as epoxy crosslinkers can limit the applicability of this strategy. [16][17][18] Another problem that arises when introducing DA moieties into the epoxy resin is related to the bismaleimide homopolymerization, which can take place at high temperatures, and results in a nonreversible crosslinking.…”

Section: Introductionmentioning

confidence: 99%

Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry

Puyadena

Calafel

Román

et al. 2021

Macro Chemistry & Physics

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Taking advantage of the reversible Diels-Alder (DA) reaction, a simple strategy to obtain recyclable epoxy resins is presented. For this purpose, blends of furan-functionalized and nonfunctionalized epoxy resin are prepared. After the addition of diamine and bismaleimide, blends are heated at 150°C for 5 min, where the permanent amine/epoxy reaction has taken place and upon cooling to room temperature the reversible DA reaction has happened, giving rise to a dual permanent/nonpermanent network. Both reactions are confirmed by Fourier-transform infrared (FTIR) and 13 C-crosspolarization, magic-angle spinning (CP/MAS) nuclear magnetic resonance (NMR). Modulated differential scanning calorimetry (MDSC)shows that the epoxy/amine and bismaleimide/amine curing reaction take place, after the DA reaction, simultaneously with the retroDA reaction and before the bismaleimide homopolymerization. Therefore, under the appropriate curing conditions, the Michael's addition and the bismaleimide homopolymerization do not avoid the formation of a hybrid network, as stated in other reports. The reversibility of the DA reaction in three consecutive cycles is confirmed by DSC. Finally, the dual-cured sample is reprocessed three times without significant loss of mechanical properties.

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“…The use of Diels–Alder [4 + 2] cycloaddition (DA) in the preparation of thermally reversible polymeric materials has been explored extensively in the last three decades. [ 1–4 ] The possibility to reversibly decouple the DA adduct at relatively low temperature (retro‐DA), allows the introduction of reversible cross‐links, thus the preparation of self‐healing and shape‐memory materials, [ 5–7 ] as well as recyclable thermosets, [ 8 ] and reversible fiber reinforced composites, [ 9,10 ] with potentially limitless application, usually in the fields of smart coatings, [ 11–13 ] adhesives, [ 14 ] hydrogels [ 15–17 ] and 3D printing. [ 18 ] The probably most exploited diene/dienophile couple for this purpose is constituted by a furan/maleimide system.…”

Section: Introductionmentioning

confidence: 99%

A Structure‐Properties Relationship Study of Self‐Healing Materials Based on Styrene and Furfuryl Methacrylate Cross‐Linked via Diels–Alder Chemistry

Raffa

Kassi

Gosschalk

et al. 2021

Macro Materials & Eng

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A series of copolymers of styrene and furfuryl methacrylate characterized by various molecular structures (linear and star, block and random) is synthesized via atom transfer radical polymerization, and cross‐linked with a bismaleimide by means of thermally reversible Diels–Alder (DA) reaction, to obtain self‐healing materials. The prepared materials are studied in terms of gelation, swelling, thermal, and dynamic‐mechanical analysis, with the aim of correlating relevant properties to their chemical structure. It is found that the furan/styrene ratio, as well as the molecular architecture, have a major influence on the properties. It is also found that the reversibility of the DA reaction is not complete in the solid state for materials with high cross‐linking density. This study provides some important tools for the design of materials characterized by thermally reversible behavior, which find usually application as self‐healing thermosets, coatings, or adhesives.

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Simultaneous Recovery of Matrix and Fiber in Carbon Reinforced Composites through a Diels–Alder Solvolysis Process

Cited by 31 publications

References 56 publications

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

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

Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry

A Structure‐Properties Relationship Study of Self‐Healing Materials Based on Styrene and Furfuryl Methacrylate Cross‐Linked via Diels–Alder Chemistry

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