Epoxy resins based on resorcinol and its derivatives

Sorokin, V. P.; Bobylev, V. A.; Eselev, A. D.

doi:10.1134/s1811238207030149

Cited by 6 publications

(5 citation statements)

References 3 publications

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“…[42][43][44] Resorcinol is one of the chemical valorization products of cellulose or lignocellulosic biomass, [45,46] which can simply be converted into diglycidyl resorcinol ether (DGRE) in a single step using bio-based epichlorohydrin alternative Epicerol, a registered trademark of Solvay. [47,48] Herein, a straightforward approach for vitrimer synthesis and corresponding composites, using an industrially relevant epoxy-amine chemistry protocol, is proposed. In this context, the resorcinol-derived DGRE will be investigated in the curing process in combination with a siloxane amine that is used with the aim to produce vitrimer materials showing fast dynamic exchange.…”

Section: Introductionmentioning

confidence: 99%

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Resorcinol‐Derived Vitrimers and Their Flax Fiber‐Reinforced Composites Based on Fast Siloxane Exchange

Debsharma

Engelen

Baere

et al. 2023

Macromol. Rapid Commun.

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Natural fiber‐reinforced composites are gaining increased interest for their significantly reduced carbon footprint compared to conventional glass or carbon fiber‐based counterparts. In this study, natural fibers are used in a resorcinol‐based epoxy resin that is thermally reshapable at higher temperatures (>180 °C) by using fast exchanging siloxane bonds, catalyzed by 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene. Stress relaxation times of only about 6 s at 220 °C can be reached. A resorcinol‐based epoxy compound is selected because it can be derived from cellulose, opening ways for more sustainable and reshapable composite materials. In a last step of the research, the low viscosity vitrimer formulation (<200 mPa s) is applied to make a flax fiber‐reinforced composite using an industrially relevant vacuum‐assisted resin infusion process. A section of this composite is successfully reshaped, which allows for envisioning a second life for natural fiber‐reinforced composites.

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Section: Introductionmentioning

confidence: 99%

“…[ 42–44 ] Resorcinol is one of the chemical valorization products of cellulose or lignocellulosic biomass, [ 45,46 ] which can simply be converted into diglycidyl resorcinol ether (DGRE) in a single step using bio‐based epichlorohydrin alternative Epicerol, a registered trademark of Solvay. [ 47,48 ]…”

Section: Introductionmentioning

confidence: 99%

Resorcinol‐Derived Vitrimers and Their Flax Fiber‐Reinforced Composites Based on Fast Siloxane Exchange

Debsharma

Engelen

Baere

et al. 2023

Macromol. Rapid Commun.

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“…Epoxy polymers with aromatic units are somehow required to have high thermosetting performances. Resorcinol diglycidyl ether (RE) obtained from resorcinol, a meta-substituted diphenol is a commercially available product and has been already used to form biobased epoxy resins. − Furthermore, eugenol is an aromatic molecule extracted from cloves in which the allylic function and the phenolic group allows various functionalizations . Tri(epoxized-eugenyl)phosphate has been synthesized by treating phosphorus oxychloride with eugenol followed by epoxidation with m -CPBA .…”

Section: Introductionmentioning

confidence: 99%

Resorcinol-Based Epoxy Resins Hardened with Limonene and Eugenol Derivatives: From the Synthesis of Renewable Diamines to the Mechanical Properties of Biobased Thermosets

Mattar

Anda

Vahabi

et al. 2020

ACS Sustainable Chem. Eng.

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Synthesis of fully eco-friendly thermosets based on renewable resorcinol diglycidyl ether (RE) hardenered with different biobased diamines having aliphatic, cyclic, or aromatic backbones were prepared. Two diamines were successfully synthesized from d-limonene and allyl-eugenol by thiol–ene addition in the presence of cysteamine hydrochloride to obtain cyclic diamine-limonene (DA-LIM) and aromatic diamine-allyl eugenol (DA-AE), respectively. New thermosets RE/HDMA (hexamethylene diamine), RE/DA-LIM, and RE/DA-AE were further obtained by an epoxy-amine curing process. Thermal stability, flammability, and mechanical properties were investigated by thermogravimetric analysis (TGA), pyrolysis combustion flow calorimeter (PCFC), and dynamic mechanical analysis (DMA), respectively. Although the α transition temperature T α of the cyclic and aromatic biobased thermosets were lower than the one based on HDMA (∼95 °C instead of 110 °C), the flexural moduli were comparable (>2 GPa). Interestingly though, it was observed that their fracture toughness behavior (K IC and G IC) is attractive, as the G IC of the cyclic biobased resin RE/DA-LIM (208 J/m2) is practically two times greater than that of RE/HMDA (90 J/m2). Indeed, the fully biobased thermosets containing cyclic or aromatic diamines offer an outstanding compromise between high stiffness and high fracture toughness properties. In terms of thermal stability, RE/DA-AE exhibits a char yield higher than RE/DA-LIM (21% vs 10%) which could lead to a potential material having better flame retardancy. These results suggested that the aromatic biobased epoxy/amine resin would be well suited for reinforced composite materials and could potentially be used as an alternative to current thermosets.

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“…The amount of unsaturation, that is, acrylate functional groups, is much higher in the resorcinol epoxy acrylate (REA) oligomer when compared to conventional bisphenol A epoxy acrylate, which will successively lead to optimum cross-linking at the curing stage. 3 It also exhibits low viscosity, a fast curing rate, high strength, and excellent thermal stability. 4 Moreover, it also has excellent wetting and dispersing properties, which aids in uniform blending for pigments, fillers, and additives.…”

Section: ■ Introductionmentioning

confidence: 99%

“…These resorcinol-based polymers have established a diverse profile for their applications as adhesives, coatings, plastic moldings, rubber composites, etc. , The reported studies reveal that the resorcinol-based epoxy acrylate resin exhibits the quality of a high-performance material. The amount of unsaturation, that is, acrylate functional groups, is much higher in the resorcinol epoxy acrylate (REA) oligomer when compared to conventional bisphenol A epoxy acrylate, which will successively lead to optimum cross-linking at the curing stage . It also exhibits low viscosity, a fast curing rate, high strength, and excellent thermal stability .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Fiber-Reinforced Resorcinol Epoxy Acrylate Applied to Stereolithography 3D Printing

Desai

Jagtap

2021

ACS Omega

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As perceived, fiber-reinforced photocuring resins possess various distinctive advantages over traditional reinforced resin systems. This includes a rapid curing rate, energy efficiency, no volatile organic compounds, high strength, good thermal stability, and chemical resistance. Printing 3D composite objects using vat polymerization techniques has been a center of interest where photocuring resins are applied. In our present study, we have synthesized resorcinol-based diglycidyl ether, that is, a resorcinol-based epoxy resin, and further acrylated to the resorcinol epoxy acrylate oligomer. This oligomer was further formulated to photocuring resins using a suitable quantity of reactive diluents and photoinitiators. Now, three types of synthetic fibers, that is, glass fibers, nylon fibers, and polyester fibers, were incorporated in this formulated resin at different loading percentages. The oligomer synthesized was analyzed for structural conformation using Fourier transform infrared spectroscopy and 13C nuclear magnetic resonance. Further, we comparatively examined the rheological behavior of prepared formulations, and compatible formulations were applied to stereolithography 3D printers. Finally, physical, mechanical, thermal, transmittance, and morphological characteristics were comparatively analyzed for prepared UV-cured composites. The outcomes obtained during characterizations of UV-cured composites will be inevitably reflected in 3D-printed objects.

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Epoxy resins based on resorcinol and its derivatives

Cited by 6 publications

References 3 publications

Resorcinol‐Derived Vitrimers and Their Flax Fiber‐Reinforced Composites Based on Fast Siloxane Exchange

Resorcinol‐Derived Vitrimers and Their Flax Fiber‐Reinforced Composites Based on Fast Siloxane Exchange

Resorcinol-Based Epoxy Resins Hardened with Limonene and Eugenol Derivatives: From the Synthesis of Renewable Diamines to the Mechanical Properties of Biobased Thermosets

Synthesis and Characterization of Fiber-Reinforced Resorcinol Epoxy Acrylate Applied to Stereolithography 3D Printing

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