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

Raffa, Patrizio; Kassi, Adamantia; Gosschalk, Julian; Migliore, Nicola; Polgar, Lorenzo Massimo; Picchioni, Francesco

doi:10.1002/mame.202170010

Cited by 5 publications

(4 citation statements)

References 44 publications

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“…Furan/maleimide chemistry has been used to crosslink rubbers, [ 14,76,78 ] poly sacharides, [ 5,10,13 ] carbon‐nanotubes, [ 79 ] poly ketones, [ 47 ] polyacrylates, [ 80 ] and poly ethers [ 55 ] to yield recyclable thermosets. The studies discussed in this section cover solely systems for which the kinetics were analyzed, The collected data are listed in Table 3 .…”

Section: Effect Of Architecture On Reported Kineticsmentioning

confidence: 99%

Designing End‐of‐Life Recyclable Polymers via Diels–Alder Chemistry: A Review on the Kinetics of Reversible Reactions

Tempel

Picchioni

Bose

2022

Macromol. Rapid Commun.

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The purpose of this review is to critically assess the kinetic behavior of the furan/maleimide Diels-Alder click reaction. The popularity of this reaction is evident and still continues to grow, which is likely attributed to its reversibility at temperatures above 100 °C, and due to its biobased "roots" in terms of raw materials. This chemistry is used to form thermoreversible crosslinks in polymer networks, and thus allows the polymer field to design strong, but also end-of-life recyclable thermosets and rubbers. In this context, the rate at which the forward reaction (Diels-Alder for crosslinking) and its reverse (retro Diels-Alder for decrosslinking) proceed as a function of temperature is of crucial importance in assessing the feasibility of the design in real-life products. Differences in kinetics based from various studies are not well understood, but are potentially caused by chemical side groups, mass transfer limitations, and the analysis methods being employed. In this work, all the relevant studies are attempted to be placed in perspective with respect to each other, and thereby offer a general guide is offered on how to assess their recycling kinetics.

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Section: Effect Of Architecture On Reported Kineticsmentioning

confidence: 99%

Designing End‐of‐Life Recyclable Polymers via Diels–Alder Chemistry: A Review on the Kinetics of Reversible Reactions

Tempel

Picchioni

Bose

2022

Macromol. Rapid Commun.

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“…Hence, they can lead to thermoreversible crosslinked materials, which can be used as thermoresponsive materials. Accordingly, RDRP copolymers containing FMA repeat units have been widely investigated for applications such as self‐healing materials, [ 129–132 ] responsive nanoparticles, [ 133 ] smart hydrogels, [ 134 ] and surfaces. [ 135 ] Representative examples are self‐healable materials based on well‐defined ABA triblock copolymers containing reactive PFMA end blocks.…”

Section: Well‐defined Poly(meth)acrylates Based On Lignocellulosic Su...mentioning

confidence: 99%

RDRP (Meth)acrylic Homo and Block Polymers from Lignocellulosic Sugar Derivatives

Palà

Woods

Hatton

et al. 2022

Macro Chemistry & Physics

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Currently, most commodity chemicals and polymers are manufactured from nonrenewable petroleum-based resources. However, due to its finite nature and social claims about environment preservation, alternative sources of value-added and building block chemicals are being intensively studied. Renewable lignocellulosic biomass has offered an attractive replacement for fossil-based chemicals. Lignin and C5/C6 sugars obtained from lignocellulosic biomass through chemical and enzymatic methods can be further transformed to targeted chemical platforms. In the present review, synthetic pathways for well-defined poly(meth)acrylates obtained from C5/C6 sugar-derived platforms in which the sugar structure is not retained are discussed. While bio-based polymers from these monomers are investigated using a wide range of polymerization techniques, this study focuses on precise synthesis of macromolecular structures taking advantage of reversible-deactivation radical polymerization methods and their applications.

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“…CANs operate on the principle of dynamic covalent chemistry, , where covalent bonds can exchange over time, as opposed to supramolecular chemistry, where noncovalent bonds can exchange. Examples of dynamic covalent bonds used in CANs are the Diels–Alder reaction, , N,S-acetals, nucleophilic transalkylation reactions, imines, − disulfides, − esters, , vinylogous urethanes, , diketoamines, , acylsemicarbazides, , and boronic esters. − In this study, we chose to use the well-known boronic ester bond, on which we reported previously, , for the formation of dynamically cross-linked networks. , …”

Section: Introductionmentioning

confidence: 99%

Recyclable Covalent Adaptable Polystyrene Networks Using Boronates and TetraAzaADamantanes

van Hurne,

Raut,

Smulders

2024

ACS Appl. Polym. Mater.

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With an ever-increasing annual production of polymers and the accumulation of polymer waste leading to progressively adverse environmental consequences, it has become important that all polymers can be efficiently recycled at the end of their life cycle. Especially thermosets are intrinsically difficult to recycle because of their permanent covalent cross-links. A possible solution is to switch from using thermosets to covalent adaptable networks, sparking the rapid development of novel dynamic covalent chemistries and derived polymer materials. Next to development of these innovative polymer materials, there is also an evident advantage of merging the virtues of covalent adaptable networks with the proven material properties of widely used commodity plastics, by introducing dynamic covalent bonds in these original thermoplastic materials to obtain recyclable thermosets. Here we report the synthesis and characterization of a polystyrene polymer, functionalized with TetraAzaADamantanes and cross-linked with dynamic covalent boronic esters. The material properties were characterized for different degrees of crosslinking. The materials showed good solvent resistance with a high remaining insoluble fraction. In line with the typical behavior of traditional covalent adaptable networks, the prepared polystyrene-based boronate-TetraAzaADamantane materials were able to undergo stress relaxation. The material relaxation was also shown to be tunable by mixing with an acid catalyst. Lastly, the materials could be recycled at least 2 times.

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

Abstract: 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.

Cited by 5 publications

References 44 publications

Designing End‐of‐Life Recyclable Polymers via Diels–Alder Chemistry: A Review on the Kinetics of Reversible Reactions

Designing End‐of‐Life Recyclable Polymers via Diels–Alder Chemistry: A Review on the Kinetics of Reversible Reactions

RDRP (Meth)acrylic Homo and Block Polymers from Lignocellulosic Sugar Derivatives

Recyclable Covalent Adaptable Polystyrene Networks Using Boronates and TetraAzaADamantanes

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