An Acid-/Base-Degradable Epoxy Resin Cured by 1,3,5-Triacroylamino-hexahydro-s-triazine Derivative

Wang, Lei; Shi, Yan; Zhang, Lei; Mai, Yuliang; Li, Weihao; Pang, Hao

doi:10.1007/s13233-021-9060-1

Cited by 7 publications

(5 citation statements)

References 27 publications

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“…Wang et al. implemented the commercially available 1,3,5‐triacyloyl‐hexahydro‐1,3,5‐triazine (TAHT) structure into epoxy systems [126] . By employing an aza‐Michael reaction between the hexahydrotriazine structure and ethylamine, a novel triazine derivative was synthesized containing three amide and three secondary amine functionalities (h17 ).…”

Section: Classification Of Recyclable Epoxy Thermosetsmentioning

confidence: 99%

“…In contrast, carrying out this reaction in 1 M NaOH, it was observed that the triazine rings preserved their integrity but the amide bonds were hydrolyzed. Although a depolymerization experiment was executed on the polymer, the obtained depolymerization products were neither fully characterized nor reused for recycling purposes [126] …”

Section: Classification Of Recyclable Epoxy Thermosetsmentioning

confidence: 99%

“…[123][124][125] Wang et al implemented the commercially available 1,3,5triacyloyl-hexahydro-1,3,5-triazine (TAHT) structure into epoxy systems. [126] By employing an aza-Michael reaction between the hexahydrotriazine structure and ethylamine, a novel triazine derivative was synthesized containing three amide and three secondary amine functionalities (h17). Upon curing the epoxy precursor DGEBF, p(DGEBF-h17) with T g , tensile strength, and T d5 % values of 83 °C, 71 MPa, and 260 °C, respectively, were obtained.…”

Section: Recyclable Epoxy Thermosets Based On Hexahydrotriazine Struc...mentioning

confidence: 99%

“…Although a depolymerization experiment was executed on the polymer, the obtained depolymerization products were neither fully characterized nor reused for recycling purposes. [126]…”

Section: Recyclable Epoxy Thermosets Based On Hexahydrotriazine Struc...mentioning

confidence: 99%

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Epoxy Thermosets Designed for Chemical Recycling

Türel

Dağlar

Eisenreich

et al. 2023

Chemistry An Asian Journal

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Epoxy thermosets constitute a significant portion of high-performance plastics, as they possess excellent thermal and mechanical properties that are applicable in a wide range of industries. Nevertheless, traditional epoxy networks show strict limitations regarding chemical recycling due to their covalently crosslinked structures. Although existing methods provide partial solutions for the recycling of epoxy networks, it is urgent to develop more effective, sustainable, and permanent strategies that will solve the problem at hand. For this purpose, developing smart monomers with functional groups that enable the synthesis and development of fully recyclable polymers is of great importance. This review highlights recent advancements in chemically recyclable epoxy systems and their potential to support a circular plastic economy. Moreover, we evaluate the practicality of polymer syntheses and recycling techniques, and assess the applicability of these networks in industry.

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Section: Classification Of Recyclable Epoxy Thermosetsmentioning

confidence: 99%

Section: Classification Of Recyclable Epoxy Thermosetsmentioning

confidence: 99%

Section: Recyclable Epoxy Thermosets Based On Hexahydrotriazine Struc...mentioning

confidence: 99%

“…Although a depolymerization experiment was executed on the polymer, the obtained depolymerization products were neither fully characterized nor reused for recycling purposes. [126]…”

Section: Recyclable Epoxy Thermosets Based On Hexahydrotriazine Struc...mentioning

confidence: 99%

See 2 more Smart Citations

Epoxy Thermosets Designed for Chemical Recycling

Türel

Dağlar

Eisenreich

et al. 2023

Chemistry An Asian Journal

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show abstract

“…Epoxy resin, a major thermosetting polymer possessing outstanding mechanical properties, chemical resistance, and electrical insulation properties, has versatile applications, including as coating, insulation material, construction material, and paint [ 1 , 2 , 3 , 4 , 5 ]. Epoxy adhesive has been widely employed in various applications, from automobile to building materials, owing to its excellent adhesion property [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of Cardanol-Based Flame Retardant for Enhancing the Flame Retardancy of Epoxy Adhesives

2022

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Epoxy resin has a versatile set of applications due to its excellent properties. However, its easily flammable property limits further applications. A bio-based flame retardant, cardanyl diphenylphosphate (CDPP), was successfully synthesized via condensation reaction between cardanol and diphenyl phosphoryl chloride. The chemical structure of CDPP was confirmed via 1H nuclear magnetic resonance and Fourier transform infrared spectroscopy. To overcome the flammable property of epoxy resin, different amounts of CDPP were incorporated into the epoxy resin. The thermal stability of epoxy resin with CDPP was reduced due to its phosphorus component, which had a relatively weak bond. Meanwhile, the measured char residue of epoxy resin with CDPP was increased compared to its calculated value, which indicated that CDPP promoted the formation of char residue. The limiting oxygen index of epoxy resin with CDPP was enhanced as the amount of CDPP increased from 22.1% for EP0 to 32.7% for EP10. The maximum value of the heat release rate per unit area and total heat release values of EP10 decreased by 23.23% and 12.02%, respectively, as compared to those of EP0. Additionally, single lap shear strength confirmed the improvement in the adhesion property of EP5. The lap shear strength increased to 7.19 MPa for EP5 compared to 6.27 MPa for EP0. This behavior might be due to the higher polarity of the phosphorus components. Based on the findings gathered in the present study, the incorporation of a bio-based flame retardant (CDPP) in epoxy resin has the potential for improving flame retardancy and adhesion property, which will be promising for the industrial area.

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Chemical and Solvent‐Based Recycling of High‐Performance Epoxy Thermoset Utilizing Imine‐Containing Secondary Amine Hardener

Dağlar,

Eisenreich,

Tomović

2024

Adv Funct Materials

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Epoxy thermosets are indispensable in various industrial applications due to their exceptional material properties. However, their limited recyclability poses a significant challenge for sustainability. To address this issue, integrating recyclable imine moieties into epoxy systems has emerged as a promising strategy. Despite recent advancements, challenges persist concerning the hydrolytic stability of imine‐based epoxy thermosets and the formation of irregular oligomeric structures upon depolymerization. In this study, these shortcomings are solved by designing a liquid imine monomer with secondary amine functionalities, which is subsequently reacted with commercially available epoxy monomers to produce high‐performance epoxy thermosets. Remarkably, the developed imine‐based epoxy system shows no sign of hydrolysis even under high‐temperature aqueous conditions, underscoring its potential for various industrial applications. Only the treatment with aqueous HCl results in the selective formation of exclusively well‐defined molecules, in high isolated yields after depolymerization. Crosslinking these building blocks once again yields recycled polymers with properties identical to pristine material. Moreover, it is discovered that, despite the crosslinked nature of the epoxy thermoset, the complete dissolution of the intact polymer in dichloromethane allowed for simple solvent‐based recycling. Through design on the molecular level, the recycling of imine‐based epoxy polymers is achieved via chemical and solvent‐based techniques.

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An Acid-/Base-Degradable Epoxy Resin Cured by 1,3,5-Triacroylamino-hexahydro-s-triazine Derivative

Cited by 7 publications

References 27 publications

Epoxy Thermosets Designed for Chemical Recycling

Epoxy Thermosets Designed for Chemical Recycling

Preparation and Characterization of Cardanol-Based Flame Retardant for Enhancing the Flame Retardancy of Epoxy Adhesives

Chemical and Solvent‐Based Recycling of High‐Performance Epoxy Thermoset Utilizing Imine‐Containing Secondary Amine Hardener

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