Synthesis and characterization of new bio-based poly(acylhydrazone) vanillin vitrimers

Roig, Adrià; Ramis, Xavier; Flor, Silvia De la; Serra, Àngels

doi:10.1039/d1py01694f

Cited by 26 publications

(27 citation statements)

References 44 publications

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“…The key to solving this problem is to change the stable cross-linking structure in the material [ 11 , 12 ]. A covalent adaptive network (CAN) is one effective structure to solve this problem [ 13 ]. The reversible dynamic covalent bonds include the ester bond, [ 14 , 15 , 16 ] acetal bond, imine bond, [ 17 , 18 , 19 ] disulfide bond, [ 20 , 21 , 22 , 23 ] ester bond and Diels–Alder (DA) bond [ 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

High-Strength, Degradable and Recyclable Epoxy Resin Based on Imine Bonds for Its Carbon-Fiber-Reinforced Composites

et al. 2023

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Carbon fiber (CF) is widely used in the preparation of carbon-fiber-reinforced polymer composites (CFRP) in which it is combined with epoxy resin due to its good mechanical properties. Thermosetting bisphenol A epoxy resin, as one of the most common polymer materials, is a non-renewable resource, leading to a heavy environmental burden and resource waste. To solve the above problems and achieve high mechanical and thermal properties comparable to those of bisphenol A, herein, a high-performance, degradable and recyclable bio-based epoxy resin was developed by reacting the lignin derivative vanillin with 4-amino cyclohexanol via Schiff base. This bio-based epoxy resin showed a Young’s modulus of 2.68 GPa and tensile strength of 44 MPa, 36.8% and 15.8% higher than those of bisphenol A epoxy, respectively. Based on the reversible exchange reaction of the imine bond, the resin exhibited good degradation in an acidic environment and was recoverable by heat treatment. Moreover, the prepared epoxy resin could be used to prepare carbon fiber (CF)-reinforced composites. By washing off the epoxy resin, the carbon fiber could be completely recycled. The recovered carbon fiber was well preserved and could be used again for the preparation of composite materials to realize the complete recovery and utilization of carbon fiber. This study opens a way for the preparation of high-performance epoxy resin and the effective recycling of carbon fiber.

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Section: Introductionmentioning

confidence: 99%

High-Strength, Degradable and Recyclable Epoxy Resin Based on Imine Bonds for Its Carbon-Fiber-Reinforced Composites

et al. 2023

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“…12,13 Dynamic characteristics of the epoxy CANs can realize the reuse of resin and fiber under certain stimulus conditions while maintaining the dimensional stability of the composite material. 14−38 Many different categories of epoxy CANs based on Diels−Alder bonds, 14,15 transesterification exchange, 16−23 disulfide bonds, 19,24−26 acetal linkage, 27 imine amine exchange, [28][29][30][31][32][33]39 dynamic borate, 34,35 and thiol−epoxy click reaction 36 have been developed to realize the recyclable capability of the resin and carbon fiber from CFRP composites. However, many CANs still need additional agents to obtain the recycled epoxy resins, such as H 2 O 2 , HCl, NaOH, KOH, or relevant monomers (Table S1).…”

Section: Introductionmentioning

confidence: 99%

Carbon Fiber Reinforced Epoxy Resin Composites with Excellent Recyclable Performance via Dynamic Acylsemicarbazide Moieties

Yang

Wang

Zhang

et al. 2023

ACS Appl. Polym. Mater.

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Achieving the recycling of the carbon fiber reinforced epoxy resin composite is of great significance toward pursuing a sustainable and circular economy but remains a challenge due to the infusible and insoluble properties of epoxy resin. In this study, the acylsemicarbazide (ASC) moieties are introduced into the network to obtain the dynamic reversible cross-linked thermoset epoxy resin (EPOXY-ASC). An optimized EPOXY-ASC with a tensile stress of 81.27 MPa and an elongation at break of 13.80% exhibits excellent reprocessing performance due to the dynamic reversibility of ASC moieties. The carbon fiber reinforced polymer composites with the EPOXY-ASC resin were successfully prepared with an interlaminar shear strength of 44.86 MPa and can be fully recycled by a solvolysis method without additional agents. The recycled carbon fiber and resin still maintain the original properties well. This study provides a solution to recycle the CFRP composite, which conforms to a circular economy.

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“…In them, the bond exchange is produced in a concerted way, without any intermediate state, without losing the network integrity and always keeping the cross-linking density constant . Many organic reactions have been studied as a potential dynamic process in vitrimers such as transesterification, − disulfide metathesis, − transamination of vinylogous urethanes, , trans -thiocarbamoylation, , and imine exchange, − among others.…”

Section: Introductionmentioning

confidence: 99%

Vitrimeric Epoxy-Amine Polyimine Networks Based on a Renewable Vanillin Derivative

Roig

Hidalgo

Ramis

et al. 2022

ACS Appl. Polym. Mater.

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A series of bio-based polyimine vitrimers was obtained and characterized. A diimine-diglycidyl monomer (DIDG) was synthesized by condensing vanillin with 4,4′-oxydianiline (ODA) and further glycidylation with epichlorohydrin. This compound was cross-linked with three different Jeffamines (Jeff230, JeffD400, and JeffT403) with a different number of poly(propylene glycol) units in their structure and different functionalities. Trimethylolpropane triglycidyl ether (TMPTE) was added to the formulation to improve the thermal, mechanical, and thermomechanical properties. All of the materials prepared showed T g’s above 66 °C, good vitrimeric behavior being the maximum relaxation rate reached by the material prepared from JeffD400, which also allows the most extensive degradation when treated with an acidic aqueous solution. These polyimine vitrimers can entirely relax the stress in less than 10.5 min at 150 °C without any added catalyst. All of the materials prepared could be satisfactorily recycled up to 200 °C also presenting an excellent self-welding ability.

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Synthesis and characterization of new bio-based poly(acylhydrazone) vanillin vitrimers

Abstract: New poly(acylhydrazone) vitrimeric-type materials derived from vanillin have been studied.

Cited by 26 publications

References 44 publications

High-Strength, Degradable and Recyclable Epoxy Resin Based on Imine Bonds for Its Carbon-Fiber-Reinforced Composites

High-Strength, Degradable and Recyclable Epoxy Resin Based on Imine Bonds for Its Carbon-Fiber-Reinforced Composites

Carbon Fiber Reinforced Epoxy Resin Composites with Excellent Recyclable Performance via Dynamic Acylsemicarbazide Moieties

Vitrimeric Epoxy-Amine Polyimine Networks Based on a Renewable Vanillin Derivative

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