Thermo-reversible crosslinked natural rubber: A Diels-Alder route for reuse and self-healing properties in elastomers

Tanasi, Paolo; Santana, Marianella Hernández; Carretero‐González, Javier; Verdejo, Raquel; López–Manchado, Miguel A.

doi:10.1016/j.polymer.2019.04.059

Cited by 94 publications

(67 citation statements)

References 41 publications

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“…The Diels-Alder reaction can be applied to various polymers. Most of all, there are many studies that apply the Diels-Alder reaction to acrylate polymer, which is widely 2 of 14 used in coating materials [22][23][24][25][26][27][28][29]. In particular, the application of graphene or modified graphene oxide to self-healing polymers not only improves their mechanical properties, but also their healing efficiency [30][31][32][33][34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Lee

Cha

2020

Polymers

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In this paper, a self-healable nanocomposite based on the Diels-Alder reaction is developed. A graphene-based nanofiller is introduced to improve the self-healing efficiency, as well as the mechanical properties of the nanocomposite. Graphene oxide (GO) is modified with maleimide functional groups, and the maleimide-modified GO (mGO) enhanced the compatibility of the polymer matrix and nanofiller. The tensile strength of the nanocomposite containing 0.030 wt% mGO is improved by 172%, compared to that of a polymer film incorporating both furan-functionalized polymer and bismaleimide without any nanofiller. Moreover, maleimide groups of the surface on mGO participate in the Diels-Alder reaction, which improves the self-healing efficiency. The mechanical and self-healing properties are significantly improved by using a small amount of mGO.

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Section: Introductionmentioning

confidence: 99%

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Lee

Cha

2020

Polymers

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“…Self-healing materials are designed with the intention of extending their life span, by fully or partially repairing damage autonomously, without any external stimulus. Several healing concepts have been studied and applied to rubber matrices [13][14][15][16][17][18]. The irreversible covalent crosslinked rubber network theoretically blocks its self-healing capability, since chain mobility is required for healing to take place.…”

Section: Introductionmentioning

confidence: 99%

Giving a Second Opportunity to Tire Waste: An Alternative Path for the Development of Sustainable Self-Healing Styrene–Butadiene Rubber Compounds Overcoming the Magic Triangle of Tires

et al. 2019

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Current regulations demand tires with long lifetime and reduced fuel consumption without sacrificing car safety. However, tire technology still needs to reach a suitable balance between these three indicators. Here, we address them by developing a self-healing tire compound using styrene–butadiene rubber (SBR) as the matrix and reclaimed tire waste as the sustainable filler. The addition of ground tire rubber (GTR) to the matrix simultaneously improved the rolling resistance and maintained both wet grip and healing ability. We provide an in-depth analysis of the healing behavior of the material at a scale close to the relevant molecular processes through a systematic dynamic-mechanical and dielectric analysis. We found that SBR and SBR/GTR compounds show a complete recovery of stiffness and relaxation dynamics after being damaged by cyclic deformation, resulting in a heterogeneous repaired rubber network. This new development could well overcome the so-called magic triangle of tires, which is certainly one of the key objectives of the tire industry.

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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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Thermo-reversible crosslinked natural rubber: A Diels-Alder route for reuse and self-healing properties in elastomers

Cited by 94 publications

References 41 publications

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Improvement of Mechanical and Self-Healing Properties for Polymethacrylate Derivatives Containing Maleimide Modified Graphene Oxide

Giving a Second Opportunity to Tire Waste: An Alternative Path for the Development of Sustainable Self-Healing Styrene–Butadiene Rubber Compounds Overcoming the Magic Triangle of Tires

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

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