Blended vinylogous urethane/urea vitrimers derived from aromatic alcohols

Haida, Philipp; Signorato, Gloria; Abetz, Volker

doi:10.1039/d1py01237a

Cited by 19 publications

(14 citation statements)

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“…Vinylogous urethane is another associative dynamic bond, which is commonly incorporated into polymeric systems. There are several reports of intrinsic self-healing polymers with vinylogous urethane bonds. − Among them, poly((2-acetoacetoxy)ethyl methacrylate/methyl methacrylate/ n -butyl acrylate) P(AAEMA/MMA/nBA) copolymer networks show significant advancement (Figure c) . These networks are processable by compression molding at 120 °C and exhibit room temperature self-healing.…”

Section: Representative Intrinsic Self-healing Polymersmentioning

confidence: 99%

Intrinsically Self-Healing Polymers: From Mechanistic Insight to Current Challenges

et al. 2022

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Self-healing materials open new prospects for more sustainable technologies with improved material performance and devices' longevity. We present an overview of the recent developments in the field of intrinsically self-healing polymers, the broad class of materials based mostly on polymers with dynamic covalent and noncovalent bonds. We describe the current models of self-healing mechanisms and discuss several examples of systems with different types of dynamic bonds, from various hydrogen bonds to dynamic covalent bonds. The recent advances indicate that the most intriguing results are obtained on the systems that have combined different types of dynamic bonds. These materials demonstrate high toughness along with a relatively fast self-healing rate. There is a clear trade-off relationship between the rate of self-healing and mechanical modulus of the materials, and we propose design principles of polymers toward surpassing this trade-off. We also discuss various applications of intrinsically self-healing polymers in different technologies and summarize the current challenges in the field. This review intends to provide guidance for the design of intrinsic self-healing polymers with required properties. CONTENTS 4.3.4. Waiting Time 5. Applications of Intrinsically Self-Healing Polymers 5.1. Intrinsic Self-Healing Polymers for Additive Manufacturing 5.2. Intrinsic Self-Healing Polymers for Envelope Applications 5.3. Intrinsic Self-Healing Polymers for Energy Storage 5.4. Intrinsic Self-Healing Polymers for Stretchable Electronics 6. Current Challenges and Future Perspectives 6.1. Trade-off between Self-Healing Kinetics and Mechanical Strength 6.2. Employing Complex Architectures and Combination of Dynamic Bonds to Surpass the Modulus−Self-Healing Rate Trade-off 6.3. Needs for in Situ Analysis of Self-Healing 6.4. Theoretical and Modeling Challenges 7. Conclusions and Outlook Author Information

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Section: Representative Intrinsic Self-healing Polymersmentioning

confidence: 99%

Intrinsically Self-Healing Polymers: From Mechanistic Insight to Current Challenges

et al. 2022

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“…Given the unique feature of muti‐site reactive ability, acetoacetate group can mediate many classical reactions such as Michael addition reaction and transamination of vinylogous urethane under mild conditions. [ 25‐41 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Covalently Crosslinked Networks from Telechelic Polycyclooctene with Reinforced Properties

Zheng

Liu

et al. 2023

Chin. J. Chem.

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Comprehensive Summary Introducing covalently crosslinked network to telechelic polymers can enable the formation of advanced polymeric materials with enhanced material properties. In this contribution, well‐defined telechelic polymers bearing acetoacetate groups were synthesized via Ru‐catalyzed ring‐opening metathesis polymerization of cyclooctene in the presence of chain transfer agents. Given the unique feature of muti‐site reactive acetoacetate end groups, several crosslinked networks were constructed using different crosslinkers under mild conditions. In the Michael addition reaction system, the introduction of di/trifunctional aliphatic acrylate as crosslinkers significantly enhanced the mechanical properties of the generated crosslinked network (tensile strength up to 27 MPa, elongation at break up to 500%). On the other hand, vitrimers with dynamic covalent crosslinked networks were accessed via transamination of vinylogous urethane reaction using telechelic polymers and tris(2‐aminoethyl)amine. These vitrimers presented great mechanical properties and reprocessing properties. These strategies can be potentially applied to construct other types of high‐performance polymeric materials.

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“…Based on the reversible cross‐linking mechanism, CANs are divided into two types: in dissociative CANs; crosslinks first open and then new crosslinks form during heating, while in associative CANs; exchange reactions in the crosslinks occur in such a way that the crosslink density is constant. [ 17–21 ]…”

Section: Introductionmentioning

confidence: 99%

“…[ 25 ] Various associative exchange mechanisms in vitrimers have been studied, for example, transesterification, [ 26,27 ] transcarbamoylation, [ 28,29 ] transesterification, [ 30,31 ] and transamination of vinylogous urethanes. [ 21,25 ] Denissen and coworkers investigated a catalyst‐free synthetic route of vinylogous urethane vitrimers. [ 2 ] These vitrimers can be easily synthesized with commercially available chemicals and have excellent mechanical and recyclable properties.…”

Section: Introductionmentioning

confidence: 99%

“…Based on the reversible cross-linking mechanism, CANs are divided into two types: in dissociative CANs; crosslinks first open and then new crosslinks form during heating, while in associative CANs; exchange reactions in the crosslinks occur in such a way that the crosslink density is constant. [17][18][19][20][21] Recently, vitrimers have been developed as a new class of plastics with an associative exchange mechanism. They are thermoreversible covalent adaptable networks, in which a thermal trigger conducts a dynamic exchange of crosslinks, [22][23][24] resulting in reprocessable materials with reproducible properties.…”

Section: Introductionmentioning

confidence: 99%

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Tailor‐Made Vinylogous Urethane Vitrimers Based on Binary and Ternary Block and Random Copolymers: An Approach toward Reprocessable Materials

Weerathaworn

Abetz

2022

Macro Chemistry & Physics

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Vitrimers are promising reprocessable materials. To tune their properties, microphase separated block copolymers as backbones play an essential role in the thermal and mechanical properties of the resulting nanostructured networks. In this study, various narrow disperse di-and triblock copolymers containing a hydroxyethyl methacrylate block and, for comparison, random copolymers of the same comonomers are synthesized in a controlled manner by photoiniferter reversible addition-fragmentation chain transfer polymerization. Subsequently, the copolymers are modified by acetoacetate groups and cross-linked with diamines. After curing, the di-and triblock copolymer-based vitrimers exhibit excellent thermal and mechanical properties compared to random ones; moreover, their characteristic properties can be adjusted by different types and amounts of diamines. As the transamination reaction is a thermoreversible exchange reaction, the resulting vitrimers are reprocessable and therefore are recyclable materials. The combining of two of these classes of soft materials, namely vitrimers and block copolymers, leads to materials with a broad spectrum of adjustable mechanical properties for various applications with an improved end-of-life management, when compared to permanently crosslinked thermosets.

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Blended vinylogous urethane/urea vitrimers derived from aromatic alcohols

Abstract: Vitrimers belong to the class of covalent adaptable networks and are cross-linked polymers, which undergo dynamic, associative exchange reactions under thermal treatment, making these networks permanent as well as dynamic....

Cited by 19 publications

References 64 publications

Intrinsically Self-Healing Polymers: From Mechanistic Insight to Current Challenges

Intrinsically Self-Healing Polymers: From Mechanistic Insight to Current Challenges

Covalently Crosslinked Networks from Telechelic Polycyclooctene with Reinforced Properties

Tailor‐Made Vinylogous Urethane Vitrimers Based on Binary and Ternary Block and Random Copolymers: An Approach toward Reprocessable Materials

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