Epoxy vitrimers with a covalently bonded tertiary amine as catalyst of the transesterification reaction

Altuna, Facundo Ignacio; Hoppe, Cristina Elena; Williams, Roberto J. J.

doi:10.1016/j.eurpolymj.2019.01.045

Cited by 143 publications

(132 citation statements)

References 25 publications

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“…In an elegant article by Altuna and co-workers, a tertiary amine catalyst was covalently introduced in epoxy vitrimers using a primary or secondary amine that reacted with the matrix constituents. 30 Due to the ability of tertiary amines to catalyse transesterication reactions through general base catalysis, this material design enabled exchange reactions without the addition of external catalysts, solving partially some related drawbacks thereof. A similar but more elaborate strategy was introduced by Guo, Zhang and co-workers who introduced very hydroxyl-rich monomers, like glycerol or hyperbranched epoxy precursors to accelerate the rate of the non-catalysed transesterication.…”

Section: Internal Catalysis and Neighbouring Group Participation (Ngp)mentioning

confidence: 99%

Vitrimers: directing chemical reactivity to control material properties

et al. 2020

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Section: Internal Catalysis and Neighbouring Group Participation (Ngp)mentioning

confidence: 99%

Vitrimers: directing chemical reactivity to control material properties

et al. 2020

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“…Firstly, the commonly used catalysts are usually not bound in the network and have poor compatibility with organic compounds [ 40 ]. High catalyst loading may lead to the aggregation and leaching of catalysts, resulting in a decrease in the material performance [ 16 , 46 ]. Secondly, these catalysts are toxic and corrosive, which may cause corrosion damage to materials [ 47 ].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, researchers developed a new type of catalyst-free epoxy vitrimers by introducing abundant hydroxyl groups or covalently bonded tertiary amines as the internal catalyst of TERs [ 46 , 47 , 49 , 50 ]. However, these polymers usually had the problems of complex synthesis processes, low glass transition temperatures ( T g ), and low strengths.…”

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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“…They obtained a gel when the ratio epoxy to acid groups was higher than 3, but with a drop of Tg from 90 to 0°C. Recently, Altuna et al 46 synthesised poly hydroxy-ester vitrimer networks with a fraction of nonexchangeable amine links as internal catalysts in the network, they developed a statistical analysis of the network structure to estimate the partition of the tertiary amine between sol and gel fractions.…”

mentioning

confidence: 99%