Highly reprocessable, room temperature self-healable bio-based materials with boronic-ester dynamic cross-linking

Tajbakhsh, Saeid; Hajiali, Faezeh; Guinan, Kieran J.; Marić, Milan

doi:10.1016/j.reactfunctpolym.2020.104794

Cited by 13 publications

(32 citation statements)

References 89 publications

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“…It was previously shown that polymers containing boronic ester bonds have selfhealing properties at room temperature because of the ability of boronic ester groups to change bonds (associative dynamic covalent network) within the polymer structure in the presence of water. 17 In this study, the network formation probably happened during the film formation process, and boronic ester bonds can be formed between polymer chains, while the polymers remained relatively flexible because of the relatively low melting point. There was a sufficient concentration of water in the early drying stages to permit some movement before the polymers eventually stiffened as the water was evaporated.…”

Section: ■ Results and Discussionmentioning

confidence: 80%

“…51 Furthermore, similar results (G′ > G″ for frequencies lower than the crossover) were obtained in our previous studies on the polymers with similar compositions. 17,22 By increasing the BG dimer content, the G′ increased, while preserving the linear trend and constant value up to ω ≅ 100 rad s −1 . For dimer 5% and 10%, a minimum was observed for G″, which shows the quasi-solid-like properties for these polymers.…”

Section: ■ Results and Discussionmentioning

confidence: 97%

“…22 Based on our previous study, a lower incorporation of vinylic head of BG dimer into the polymer chains is expected compared to the methacrylic group. 17 This probably results in the incomplete incorporation of some BG dimers into the polymer chains. A schematic miniemulsion polymerization of the monomers is presented in Figure 1.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…22 This decrease in T dec,1 's is even higher if it is compared to our previous results on boronic ester cross-linked polymer blends with similar monomer compositions (ΔT dec,1 up to 104 °C). 17 The difference in T dec,1 's is due to the presence of unreacted monomers, surfactant, and costabilizer within the polymer chains. The decomposition temperatures at highest weight loss (T dec,max ) for the prepared samples were significantly higher than the IBOMA/C13MA copolymers with similar compositions (ΔT dec,max up to 121 °C).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…3,16 We prepared polymers containing boronic ester dynamic cross-linking bonds in an organic solvent (toluene) previously, where we attempted to use commercially available monomers with high biocontent. 17 This was done presumably to decrease the carbon footprint of the process while still getting the desirable properties incorporated into the polymer. We attempted to take our process one step farther and eliminate the use of organic solvent in the synthesis of the recyclable polymers with boronic ester dynamic crosslinks by adopting reversible deactivation radical polymerization in miniemulsion.…”

Section: ■ Introductionmentioning

confidence: 99%

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Recyclable Polymers with Boronic Ester Dynamic Bonds Prepared by Miniemulsion Polymerization

Tajbakhsh

Hajiali

Marić

2021

ACS Appl. Polym. Mater.

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Polymers with boronic ester dynamic covalent bonds were synthesized by nitroxide-mediated miniemulsion polymerization of isobornyl methacrylate (IBOMA), alkyl methacrylates (average aliphatic size of 13.0, C13MA), glycerol monomethacrylate (GMMA), and 4-vinylphenylboronic acid (VPBA). The miniemulsion polymerization of all monomers was enabled by the esterification reaction between GMMA and VPBA and the synthesis of (VPBA + GMMA) dimer prior to the polymerization. The formation of boronic ester dynamic covalent bonds was confirmed by rheological and mechanical measurements, indicating a higher stiffness by increasing the dimer content from 5% to 15% in the initial feed. Cross-linked polymers showed high reprocessing capability with a comparatively simple recycling process (at 80 °C for 45 min) and a high organic solvent absorbance of polymers (swelling ratio up to 153%). Furthermore, it was shown that the addition of VPBA and GMMA significantly improved the heat resistance of polymers up to 121 °C, compared to the IBOMA/C13MA copolymers (without GMMA and VPBA functional monomers).

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Section: ■ Results and Discussionmentioning

confidence: 80%

Section: ■ Results and Discussionmentioning

confidence: 97%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Recyclable Polymers with Boronic Ester Dynamic Bonds Prepared by Miniemulsion Polymerization

Tajbakhsh

Hajiali

Marić

2021

ACS Appl. Polym. Mater.

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Bio‐Based and Recyclable Self‐Healing Elastomer for the Application of Self‐Powered Triboelectric Nanogenerator in Low‐Temperature

Wang,

Yin,

et al. 2023

Adv Funct Materials

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The cracks in flexible triboelectric nanogenerators (TENG) cannot naturally repair themselves during low‐temperature operation, which significantly restricts their practical applications. Yet, the development of elastomers capable of self‐repair at low temperatures has remained a formidable challenge. In this study, a dual dynamic cross‐linking network using multiple hydrogen bonds and β‐hydroxy esters is constructed to fabricate a fully bio‐based elastomer known as PLMBE. This elastomer can be stretched up to an impressive 1200% of its original length and possesses a remarkable autonomous self‐healing capability even under harsh conditions, including low temperatures (−10 °C, 12 h, with a 75% efficiency rate) and exposure to supercooled, high‐concentration saline (10% NaCl solution at −10 °C, 12 h, with a 64% efficiency rate). These remarkable properties are attributed to the elastomer's low glass transition temperature (Tg) of −30 °C and the abundance of hydrogen‐bonded supramolecular interactions. Importantly, this elastomer is highly suitable as a triboelectric layer for creating bio‐based TENG (Bio‐TENG) . These results demonstrate that Bio‐TENG can achieve an impressive output power density of 2.4 W m−2, and the output voltage recovers up to 95% after self‐healing at −10 °C. Consequently, these bio‐based elastomers have promising applications in various fields, including energy storage devices.

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Dynamic Bonds: Adaptable Timescales for Responsive Materials

2022

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Dynamic bonds introduce unique properties such as self-healing, recyclability, shape memory, and malleability to polymers. Significant efforts have been made to synthesize a variety of dynamic linkers, creating a diverse library of materials. In addition to the development of new dynamic chemistries, fine-tuning of dynamic bonds has emerged as a technique to modulate dynamic properties. This Review highlights approaches for controlling the timescales of dynamic bonds in polymers. Particularly, eight dynamic bonds are considered, including urea/urethanes, boronic esters, Thiol-Michael exchange, Diels-Alder adducts, transesterification, imine bonds, coordination bonds, and hydrogen bonding. This Review emphasizes how structural modifications and external factors have been used as tools to tune the dynamic character of materials. Finally, this Review proposes strategies for tailoring the timescales of dynamic bonds in polymer materials through both kinetic effects and modulating bond thermodynamics.

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Highly reprocessable, room temperature self-healable bio-based materials with boronic-ester dynamic cross-linking

Cited by 13 publications

References 89 publications

Recyclable Polymers with Boronic Ester Dynamic Bonds Prepared by Miniemulsion Polymerization

Recyclable Polymers with Boronic Ester Dynamic Bonds Prepared by Miniemulsion Polymerization

Bio‐Based and Recyclable Self‐Healing Elastomer for the Application of Self‐Powered Triboelectric Nanogenerator in Low‐Temperature

Dynamic Bonds: Adaptable Timescales for Responsive Materials

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