Tuning the Dynamics of Enamine-One-Based Vitrimers through Substituent Modulation of Secondary Amine Substrates

Article Chemistry, Multidisciplinary

Suppressing Creep and Promoting Fast Reprocessing of Vitrimers with Reversibly Trapped Amines

Filip Van Lijsebetten et al.

Summary: A straightforward chemical strategy was developed to improve the properties of VU vitrimers by controlling the availability of exchangeable functional groups at the molecular level.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Polymer Science

Catalyst-Free Epoxy Vitrimers Based on Transesterification Internally Activated by an α-CF3 Group

Dimitri Berne et al.

Summary: This study presents a catalyst-free epoxy vitrimer with alpha-CF3-substituted ester functions, demonstrating the potential of fluorinated groups as powerful internal activators for transesterification vitrimers. The mechanical and thermal properties of the reshaped materials were similar to those of the initial ones, indicating good reprocessability and preservation of vitrimer properties.

MACROMOLECULES (2022)

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Article Chemistry, Multidisciplinary

High-T-g and Degradable Isosorbide-Based Polybenzoxazine Vitrimer

Antoine Adjaoud et al.

Summary: This work introduces new fully bio-based vitrimers derived from isosorbide, showcasing high T-g values and fast dynamic exchanges, as well as self-healing and chemical and mechanical recycling capabilities. However, the materials are prone to degradation under acidic or alkaline conditions due to the isosorbide structure.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

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Article Chemistry, Physical

Reprocessable and Recyclable Polymer Network Electrolytes via Incorporation of Dynamic Covalent Bonds

Yangju Lin et al.

Summary: This article discusses the challenges in reprocessing and recycling of polymer network electrolytes and proposes the use of dynamic covalent bonds for addressing these challenges. The study incorporates the associative dynamic vinylogous urethane motif into a poly(ethylene oxide) network electrolyte and demonstrates the reprocessability and ion conductivity of the resulting dynamic covalent network electrolyte.

CHEMISTRY OF MATERIALS (2022)

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Article Polymer Science

Relaxation of Vitrimers with Kinetically Distinct Mixed Dynamic Bonds

Laura Porath et al.

Summary: Designing materials with tunable modulus and viscosity is crucial for various applications. Vitrimers, with their dynamic bond exchange mechanism, provide an ideal platform for viscoelastic design. By using different cross-linkers with varied functionalities and kinetics, control over cross-link density and exchange kinetics can be achieved. Furthermore, combining multiple cross-linkers into a single network allows for a better understanding of the effect of multiple dynamic bonds on the viscoelastic response.

MACROMOLECULES (2022)

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Article Polymer Science

Correlation between Self-Assembled Nanostructures and Bond Exchange Properties for Polyacrylate-Based Vitrimer-like Materials with a Trans-N-Alkylation Bond Exchange Mechanism

Yuta Oba et al.

Summary: In this study, a new approach for tuning the bond exchange properties of vitrimer-like materials with self-assembled structures was demonstrated. By quaternization of pyridine side groups in polyacrylate-based random copolymers, nanoscale aggregations were formed, and the size of the aggregates varied with the length of alkyl side groups. This research provides important knowledge for analyzing the physical properties of vitrimer or vitrimer-like materials.

MACROMOLECULES (2022)

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Article Polymer Science

Reprocessable and Recyclable Chain-Growth Polymer Networks Based on Dynamic Hindered Urea Bonds

Mohammed A. Bin Rusayyis et al.

Summary: Conventional cross-linked polymers cannot be reprocessed, while covalent adaptable networks can undergo dynamic reactions and achieve recyclability. This study presents a simple method to synthesize a hindered-urea-based dynamic cross-linker, which enables the formation of reprocessable networks. These networks exhibit excellent recovery and stability, maintaining their structure even at high temperatures.

ACS MACRO LETTERS (2022)

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Article Polymer Science

Regulating the Dynamic Behaviors of Transcarbamoylation-Based Vitrimers via Mono-Variation in Density of Exchangeable Hydroxyl

Pengcheng Miao et al.

Summary: The dynamic behaviors of vitrimer can be tuned by changing the density of exchangeable hydroxyls alone. The relationship between the density of exchangeable hydroxyls and essential dynamic behavioral parameters was quantitatively discussed.

MACROMOLECULES (2022)

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Review Materials Science, Multidisciplinary

Elastic vitrimers: Beyond thermoplastic and thermoset elastomers

Jiancheng Luo et al.

Summary: Thermoset elastomers possess mechanical robustness, high thermal/chemical resistance, and good dimensional stability, making them widely used in industry and frontier research. However, the presence of permanent crosslinks significantly limits their recyclability. Vitrimers, polymer networks with associative exchangeable crosslinkers, provide a solution for the circularity of thermoset elastomers. This review focuses on the design, synthesis, fundamental physics, and property evaluation of elastic vitrimers based on different types of dynamic covalent bonds. Control over the network parameters allows for tailoring of mechanical performance, network dynamics, self-healing capability, and recyclability. The responsive behavior of elastic vitrimers to external stimuli such as temperature, light, and moisture can be controlled due to the dynamic nature of reversible chemical bonds. The review also discusses the critical physical parameters of elastic vitrimers and their comparison with commonly used thermoset and thermoplastic elastomers, as well as the merits, bottlenecks, and future research directions of elastic vitrimers for practical applications in various fields.

MATTER (2022)

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Article Materials Science, Multidisciplinary

Healable and Recyclable Polymeric Materialswith High Mechanical Robustness

Xiaokong Liu et al.

Summary: This article introduces the development and challenges of healable and recyclable polymers. It focuses on the mechanically robust polymers based on noncovalent and dynamic covalent cross-linking, as well as reinforcement strategies and emerging applications.

ACS MATERIALS LETTERS (2022)

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Article Polymer Science

Combining vinylogous urethane and β-amino ester chemistry for dynamic material design

Joshua O. Holloway et al.

Summary: This study combines vinylogous urethane (VU) and beta-amino ester chemistry to synthesize covalent adaptable networks (CANs). The thermal and rheological properties of the resulting CANs are extensively analyzed. The study shows that these CANs have good storage modulus and re-processability.

POLYMER CHEMISTRY (2022)

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Article Polymer Science

Dynamic Polyamide Networks via Amide-Imide Exchange

Yinjun Chen et al.

Summary: The diamide-imide equilibrium was utilized to synthesize dynamic covalent polymer networks with high processibility and processible viscoelasticity at elevated temperatures. The temperature-dependent mechanical properties of the materials were fully reversible, transitioning from elastic solids to predominantly viscous materials around 110 degrees Celsius.

MACROMOLECULES (2021)

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Article Polymer Science

The Crucial Role in Controlling the Dynamic Properties of Polyester-Based Epoxy Vitrimers: The Density of Exchangeable Ester Bonds (ν)

Mao Chen et al.

Summary: Vitrimer materials, which blur the boundary between thermosets and thermoplastics, have dynamic properties that can be influenced by key factors such as the density of exchangeable ester bonds. This control can impact stress relaxation behavior, activation energy, and other intrinsic parameters important for the dynamic properties of vitrimers. Adjusting the density of exchangeable bonds shows promise in designing vitrimer materials for various applications.

MACROMOLECULES (2021)

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Article Chemistry, Multidisciplinary

Reprocessable, Self-Adhesive, and Recyclable Carbon Fiber-Reinforced Composites Using a Catalyst-Free Self-Healing Bio-Based Vitrimer Matrix

Yazhou Xu et al.

Summary: The study successfully developed a chemically degradable bio-based vitrimer matrix by curing tung oil-based triglycidyl ester with menthane diamine, enabling the effective recycling of CFRCs with excellent performance.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

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Article Polymer Science

Mechanical and Structural Consequences of Associative Dynamic Cross-Linking in Acrylic Diblock Copolymers

Jacob S. A. Ishibashi et al.

Summary: The composition of low-T-g n-butylacrylate-block-(acetoxyaceto)-ethyl acrylate block polymers is investigated as a strategy to tune the properties of dynamically cross-linked vinylogous urethane vitrimers. Increasing the proportion of the cross-linkable block results in changes in thermorheological properties, structure, and stress relaxation that cannot be solely explained by increasing cross-link density. The thermomechanical and viscoelastic properties of block-copolymer-derived vitrimers are determined by the subtle interplay of microphase separation and network defects.

MACROMOLECULES (2021)

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Article Polymer Science

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

Florian Cuminet et al.

Summary: Vitrimers are promising polymer materials with chemical resistance, reshaping ability, and unique rheological behavior, but many require high catalyst loadings, limiting their potential applications; internal catalysis and neighboring group participation can enhance the reshaping ability of such materials; knowledge on the effect of activating groups on exchange reactions in Vitrimers remains scarce.

MACROMOLECULES (2021)

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Article Nanoscience & Nanotechnology

Dynamic Semicrystalline Networks of Polypropylene with Thiol-Anhydride Exchangeable Crosslinks

Mohand O. Saed et al.

Summary: Dynamic crosslinked polypropylene (xTPO) shows great potential for various applications, offering improved mechanical strength and stability through dynamic covalent bond crosslinking. The performance of xTPO material can be tailored by the degree of crosslinking, and it is easily reprocessable for multiple uses.

ACS APPLIED MATERIALS & INTERFACES (2021)

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Article Polymer Science

Polyaddition Synthesis Using Alkyne Esters for the Design of Vinylogous Urethane Vitrimers

Yann Spiesschaert et al.

Summary: Vitrimers are a type of covalent network materials with reshaping and recyclability properties. By using alkyne esters as alternative building blocks, water-free formulations and defect-free cured VU vitrimer materials can be easily obtained. This novel approach also allows for the preparation of processable epoxy materials with tunable viscoelastic properties.

MACROMOLECULES (2021)

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Article Polymer Science

Dynamic Enamine-one Bond Based Vitrimer via Amino-yne Click Reaction

Xinru Guo et al.

Summary: The vitrimer fabricated through amino-yne click chemistry exhibits superior mechanical properties and faster dynamic exchange compared to the reference vitrimer derived from amine-acetoacetate condensation, due to fewer network defects and less sterically hindered exchange reaction. The efficient and side product-free amino-yne reaction provides a powerful chemical tool for vitrimer fabrication and is potentially suitable for sealing and adhesion applications.

ACS MACRO LETTERS (2021)

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Article Polymer Science

The effect of polarity on the molecular exchange dynamics in imine-based covalent adaptable networks

Sybren K. Schoustra et al.

Summary: Research has shown that the presence of polar domains in polyimine-based CANs significantly influences both the thermal and dynamic mechanical properties of the materials, as well as the kinetics of dynamic imine bond exchange, enhancing the exchange rate greatly. The presence of polar groups surrounding reactive imine species can lead to a wider range of phase transition temperatures and affect stress relaxation processes related to network topology, local imine exchange, and diffusion-induced imine exchange in the polymer network.

POLYMER CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Molecular control over vitrimer-like mechanics - tuneable dynamic motifs based on the Hammett equation in polyimine materials

Sybren K. Schoustra et al.

Summary: This study demonstrates the fine-tuned control over macroscopic dynamic material properties using the Hammett equation in tuneable dynamic covalent polyimine materials. By systematically varying the dynamic covalent bond dynamics through selection of appropriate substituents, the research shows a correlation between Hammett parameter and various dynamic material properties. The results showcase the direct tunability and design of dynamic material properties in a quantitative and predictable manner, with the potential for recycling and self-healing over multiple cycles.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Block Copolymer Vitrimers

Jacob J. Lessard et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Polymer Science

Investigation on Self-healing Property of Epoxy Resins Based on Disulfide Dynamic Links

Zi-Jian Li et al.

CHINESE JOURNAL OF POLYMER SCIENCE (2020)

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Review Polymer Science

Vitrimers: Permanently crosslinked polymers with dynamic network topology

Nathan J. Van Zee et al.

PROGRESS IN POLYMER SCIENCE (2020)

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Article Polymer Science

Aroylacetylene-Based Amino-Yne Click Polymerization toward Nitrogen-Containing Polymers

Xu Chen et al.

MACROMOLECULES (2020)

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Article Chemistry, Multidisciplinary

Reprocessable Cross-Linked Polymer Networks: Are Associative Exchange Mechanisms Desirable?

Benjamin R. Elling et al.

ACS CENTRAL SCIENCE (2020)

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Article Polymer Science

Preparation of Multifunctional Hyperbranched Poly(β-aminoacrylate)s by Spontaneous Amino-yne Click Polymerization

Benzhao He et al.

MACROMOLECULES (2020)

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Article Chemistry, Multidisciplinary

Boronic Ester Based Vitrimers with Enhanced Stability via Internal Boron-Nitrogen Coordination

Xiaoting Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Computer Science, Artificial Intelligence

Complex Network Representation of the Structure-Mechanical Property Relationships in Elastomers with Heterogeneous Connectivity

Yoshifumi Amamoto et al.

PATTERNS (2020)

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Review Chemistry, Multidisciplinary

Internal catalysis for dynamic covalent chemistry applications and polymer science

Filip Van Lijsebetten et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Article Chemistry, Physical

Effects of dynamic covalent bond multiplicity on the performance of vitrimeric elastomers

Shuangjian Yu et al.

JOURNAL OF MATERIALS CHEMISTRY A (2020)

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Article Polymer Science

Influence of the polymer matrix on the viscoelastic behaviour of vitrimers

Yann Spiesschaert et al.

POLYMER CHEMISTRY (2020)

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Review Chemistry, Multidisciplinary

Vitrimers: directing chemical reactivity to control material properties

Marc Guerre et al.

CHEMICAL SCIENCE (2020)

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Fast surface immobilization of native proteins through catalyst-free amino-yne click bioconjugation

Yiru Zhang et al.

CHEMICAL SCIENCE (2020)

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Tuning the mechanical and dynamic properties of imine bond crosslinked elastomeric vitrimers by manipulating the crosslinking degree

Yingjun Liu et al.

POLYMER CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Closed-loop recycling of plastics enabled by dynamic covalent diketoenamine bonds

Peter R. Christensen et al.

NATURE CHEMISTRY (2019)

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Article Polymer Science

Ethynylsulfone-Based Spontaneous Amino-yne Click Polymerization: A Facile Tool toward Regio- and Stereoregular Dynamic Polymers

Xuemei Chen et al.

MACROMOLECULES (2019)

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Article Chemistry, Multidisciplinary

Poly(oxime-ester) Vitrimers with Catalyst-Free Bond Exchange

Changfei He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Malleable and Sustainable Poly(ester amide) Networks Synthesized via Melt Condensation Polymerization

Jia-Hui Chen et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2019)

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Review Chemistry, Multidisciplinary

Adaptable Crosslinks in Polymeric Materials: Resolving the Intersection of Thermoplastics and Thermosets

Georg M. Scheutz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Ambient Cross-linking System Based on the Knoevenagel Condensation Reaction between Acetoacetylated Sucrose and Aromatic Dicarboxaldehydes

Zhiyuan Cao et al.

ACS OMEGA (2019)

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Engineering of beta-Hydroxyl Esters into Elastomer-Nanoparticle Interface toward Malleable, Robust, and Reprocessable Vitrimer Composites

Yingjun Liu et al.

ACS APPLIED MATERIALS & INTERFACES (2018)

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Vitrimeric Silicone Elastomers Enabled by Dynamic Meldrum's Acid-Derived Cross-Links

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ACS MACRO LETTERS (2018)

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Bronsted-Acid-Catalyzed Exchange in Polyester Dynamic Covalent Networks

Jeffrey L. Self et al.

ACS MACRO LETTERS (2018)

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Fluorinated Vitrimer Elastomers with a Dual Temperature Response

Marc Guerre et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Spontaneous Amino-yne Click Polymerization: A Powerful Tool toward Regio- and Stereospecific Poly(β-aminoacrylate)s

Benzhao He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Effect of Sterics and Degree of Cross-Linking on the Mechanical Properties of Dynamic Poly(alkylurea-urethane) Networks

Longhe Zhang et al.

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Chemical control of the viscoelastic properties of vinylogous urethane vitrimers

Wim Denissen et al.

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Poly(thioether) Vitrimers via Transalkylation of Trialkylsulfonium Salts

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Fabrication of Liquid Crystalline Polyurethane Networks with a Pendant Azobenzene Group to Access Thermal/Photoresponsive Shape-Memory Effects

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ACS APPLIED MATERIALS & INTERFACES (2015)

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Tuning the Dynamics of Enamine-One-Based Vitrimers through Substituent Modulation of Secondary Amine Substrates

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