Recyclable cross-linked hydroxythioether particles with tunable structures via robust and efficient thiol-epoxy dispersion polymerizations

Tan, Jiaojun; Li, Chunmei; Bruycker, Kevin De; Zhang, Guoxian; Gu, Junwei; Zhang, Qiuyu

doi:10.1039/c7ra10481b

Cited by 27 publications

(18 citation statements)

References 62 publications

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“…If the catalyst concentration is not high enough, the bond-exchange reaction will be not sufficiently fast, and the shape changing and self-healing properties are limited. , However, the use of catalyst could cause at least the following three negative effects. (1) The catalysts for epoxy vitrimer are usually organic salts (i.e., zinc(II), , stannous octoate) or strong bases (i.e., DBU, TBD). These catalysts are usually toxic, which may limit the application of vitrimer.…”

Section: Introductionmentioning

confidence: 99%

A Catalyst-Free Epoxy Vitrimer System Based on Multifunctional Hyperbranched Polymer

et al. 2018

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To date, all epoxy vitrimer systems reported in the literature rely on addition of significant amounts of catalysts to achieve the dynamic transesterification reaction (TER). However, the catalysts used in vitrimers are often toxic and have poor miscibility with organic compounds, and they may further comprise the application performance like corrosion resistance. Moreover, the reprocessing and recycling properties are highly dependent on the loading amount and the type of catalyst. In this study, two hyperbranched epoxy (HBE) prepolymers are synthesized and then reacted with succinic anhydride to prepare a catalyst-free epoxy vitrimer system. It is demonstrated that both the curing during the preparation of the cross-linked materials and the TER in the resulting cross-linked materials proceed properly without addition of external catalyst. We attributed this phenomenon to the abundant free hydroxyl groups in HBE which serve as both reacting moiety and catalyst in both curing and the TER processes. At elevated temperatures (>120 °C), the TER is activated to enable fast stress relaxation of the cross-linked network. In addition, the epoxy vitrimers exhibit glass transition temperatures (T g’s) in the range 70–96 °C, excellent thermostability, and mechanical properties similar to those of the traditional epoxy materials. By taking advantages of these features, we also demonstrate a promising self-healable and catalyst-free coating.

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Section: Introductionmentioning

confidence: 99%

A Catalyst-Free Epoxy Vitrimer System Based on Multifunctional Hyperbranched Polymer

et al. 2018

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“…In order to activate TERs between ester bonds and alcoholic hydroxyl groups, sufficient high-efficiency catalysts such as Zn(Ac) 2 [ 20 , 42 ], Sn(Oct) 2 [ 43 ], TBD [ 44 ], and DBU [ 45 ] are necessary. However, the use of these special catalysts causes a series of problems, which greatly limits the wide application of epoxy vitrimers.…”

Section: Introductionmentioning

confidence: 99%

Recyclable High-Performance Epoxy-Anhydride Resins with DMP-30 as the Catalyst of Transesterification Reactions

Zhao

Wang

2021

Polymers

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Epoxy-anhydride resins are widely used in engineering fields due to their excellent performance. However, the insolubility and infusibility make the recycling of epoxy resins challenging. The development of degradable epoxy resins with stable covalent networks provides an efficient solution to the recycling of thermosets. In this paper, 2,4,6-tris(dimethylaminomethyl)phenol (DMP-30) is incorporated into the epoxy-glutaric anhydride (GA) system to prepare high-performance epoxy resins that can be recycled below 200 °C at ordinary pressure via ethylene glycol (EG) participated transesterification. The tertiary amine groups in DMP-30 can catalyze the curing reaction of epoxy and anhydride, as well as the transesterification between ester bonds and alcoholic hydroxyl groups. Compared with early recyclable anhydride-cured epoxy resins, the preparation and recycling of diglycidyl ether of bisphenol A (DGEBA)/GA/DMP-30 systems do not need any special catalysts such as TBD, Zn(Ac)2, etc., which are usually expensive, toxic, and have poor compatibility with other compounds. The resulting resins have glass transition temperatures and strengths similar to those of conventional epoxy resins. The influences of GA content, DMP-30 content, and temperature on the dissolution rate were studied. The decomposed epoxy oligomer (DEO) is further used as a reaction ingredient to prepare new resins. It is found that the DEO can improve the toughness of epoxy resins significantly. This work provides a simple method to prepare readily recyclable epoxy resins, which is of low-cost and easy to implement.

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“…In addition, the self‐healing could be achieved at room temperature. Among the various dynamic motifs including Diels–Alder, disulfide metathesis, H‐bonding, π–π interactions, metal–ligand coordination, transesterification, imine bonds, metal–ligand interaction is a promising system, in which the mechanical properties of materials can be easily tuned by the ligand/metal (L/M) ratio and the type of metal over a broad range . The most usually used metal‐ligand systems involve multidentate nitrogen‐based aromatic ligands, such as terpyridines .…”

Section: Molecular Composition Of S‐icpsmentioning

confidence: 99%

A Three‐Armed Polymer with Tunable Self‐Assembly and Self‐Healing Properties Based on Benzene‐1,3,5‐tricarboxamide and Metal–Ligand Interactions

Tan

Guan

et al. 2019

Macromol. Rapid Commun.

Self Cite

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The dynamic nature of supramolecules makes them useful in the fields of smart devices. The combination of multiple dynamic interactions in one material may bring some enhanced properties in mechanical property, self‐healing property, or recyclability. Thus, it is significantly meaningful to design new materials with multi‐dynamic bonds and clarify their bonding mechanisms. Here, a novel three‐armed polymer based on benzene‐1,3,5‐tricarboxamide (BTA) is developed and the polymer could be further complexed by metal ions to form dynamic zinc–imidazole interactions. In this system, BTA is located in the center, and the ligand‐functionalized monomer is copolymerized with n‐butyl acrylate to form three chains. This is the first time BTA is introduced to a self‐healing system to endow the polymer with assembly and self‐healing properties. The composition, chemical structure, assembly behavior, mechanical properties, and self‐healing properties of the polymer are investigated. It is revealed that the assembly behavior of the polymer depends on the BTA contents and time. The mechanical property can be easily tuned by ligand/metal ratio and is significantly adjusted by the polymer chain length and environment humidity. Long polymer chains not only contribute to good mechanical property but also promote the self‐healing process due to the effective physical entanglement.

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Recyclable cross-linked hydroxythioether particles with tunable structures via robust and efficient thiol-epoxy dispersion polymerizations

Abstract: Thiol-epoxy reactions were first exploited as a simple method for the preparation of recyclable cross-linked hydroxythioether particles with tunable structures.

Cited by 27 publications

References 62 publications

A Catalyst-Free Epoxy Vitrimer System Based on Multifunctional Hyperbranched Polymer

A Catalyst-Free Epoxy Vitrimer System Based on Multifunctional Hyperbranched Polymer

Recyclable High-Performance Epoxy-Anhydride Resins with DMP-30 as the Catalyst of Transesterification Reactions

A Three‐Armed Polymer with Tunable Self‐Assembly and Self‐Healing Properties Based on Benzene‐1,3,5‐tricarboxamide and Metal–Ligand Interactions

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