Epoxy oligomers based on eugenol cyclotriphosphazene derivatives

Киреев, В. В.; Bredov, N. S.; Bilichenko, Yu. V.; Лысенко, К. А.; Борисов, Р. С.; Чуев, В. П.

doi:10.1134/s0965545x08060035

Cited by 25 publications

(7 citation statements)

References 7 publications

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“…To the best of our knowledge, however, so far only two kinds of eugenol-based epoxy resins have been reported. Kireev et al [23,24] reported the synthesis and structural characterization of epoxy resins derived from eugenol and hexachlorocyclotriphosphazene with a very high molecular weight, but did not address their cure and ultimate properties likely due to limitation of the processing ability. Another publication [25] reported a liquid eugenol-based epoxy resin (Eu-Ep) with two epoxy groups attached to one eugenol moieties, high theoretical epoxy value of 0.846 mol/100g and the biobased content of 62.7% (the inherent weight percentage from eugenol).…”

Section: Introductionmentioning

confidence: 99%

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

Wan

Gan

et al. 2016

Chemical Engineering Journal

229

138

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Abstract:To develop functional sustainable epoxy resins, we report a novel epoxy resin (DEU-EP) with high net biobased content (70.2 wt%) derived from renewable eugenol. We comparatively study DEU-EP with a commercial bisphenol A epoxy resin (DGEBA) in the presence of a most representative aromatic diamine curing agent, 4,4'-diaminodiphenyl methane (DDM).Differential scanning calorimetry reveals that DEU-EP can be sufficiently cured by DDM at a slower rate than DGEBA. By applying an autocatalytic reaction model, we adequately simulate the curing rate of DEU-EP/DDM, and reveal its detailed kinetic mechanisms from model-free isoconversional analysis. Dynamic mechanical analysis shows that DEU-EP/DDM takes higher storage modulus up to ~97 o C than DGEBA/DDM with the glass temperature of 114 o C. Nanoindentation and thermogravimetric analysis demonstrate that compared with DGEBA/DDM, DEU-EP/DDM exhibits a 20%, 6.7% and 111% increase in Young's modulus, hardness and char yield, respectively. Microscale combustion calorimetry data show that DEU-EP/DDM expresses 55% and 38% lower heat release rate and total heat release than DGEBA/DDM, respectively.Macroscopically, the horizontal burning test approves DEU-EP/DDM can self-extinguish in a short time. Our results demonstrate that the eugenol building blocks and their arrangement greatly affect the cure behaviors of DEU-EP/DDM, and contribute significantly to its enhanced mechanical properties, high-temperature charring ability and chain motions at glass state, as well as the reduced flammability. To summarize, DEU-EP exhibits a high promise as a new sustainable epoxy monomer for fabricating high biobased content, high rigid and low flammable epoxy materials.

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Section: Introductionmentioning

confidence: 99%

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

Wan

Gan

et al. 2016

Chemical Engineering Journal

229

138

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“…Moreover, eugenol exhibits several pharmacological properties, such as antibacterial and antioxidant properties, because of the presence of phenol groups, leading to its utilization in perfume, cosmetic and flavoring applications . So far numerous studies have used eugenol as a building block for the synthesis of bio‐based polymers, such as benzoxazine resins, allyl‐etherified eugenol, polyester resins, cyanate ester resins, bismaleimide, epoxy resins, methacrylated eugenol (ME), etc . Among them, ME, prepared by incorporation of a polymerizable methacrylate group to eugenol, shows promising potential for use as a co‐monomer replacement for styrene in VE resins because both methacrylate groups and allyl groups can participate in free radical polymerization.…”

Section: Introductionmentioning

confidence: 99%

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

Zhang

Thakur

et al. 2018

Polymer International

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A renewable chemical, eugenol, is methacrylated to produce methacrylated eugenol (ME) employing the Steglich esterification reaction without any solvent. The resulting ME is used as a low‐viscosity co‐monomer to replace styrene in a commercial epoxy‐based vinyl ester resin (VE). The volatility and viscosity of ME and styrene are compared. The effect of ME loading and temperature on the viscosity of the VE–ME resin is investigated. Moreover, the thermomechanical properties, curing extent and thermal stability of the fully cured VE–ME thermosets are systematically examined. The results indicate that ME is a monomer with low volatility and low viscosity, and therefore the incorporation of ME monomer in VE resins allows significant reduction of viscosity. Moreover, the viscosity of the VE–ME resin can be tailored by adjusting the ME loadings and processing temperature to meet commercial liquid molding technology requirements. The glass transition temperatures of VE–ME thermosets range from 139 to 199 °C. In addition, more than 95% of the monomer is incorporated and fixed in the crosslinked network structure of VE–ME thermosets. Overall, the developed ME monomer exhibits promising potential for replacing styrene as an effective low‐viscosity co‐monomer. The VE–ME resins show great advantages for use in polymer matrices for high‐performance fiber‐reinforced composites. This work is of great significance to the vinyl ester industry by providing detailed experimental support. © 2018 Society of Chemical Industry

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“…In a first study 63 Kireev et al reported authors proposed some hypotheses on the nature of side reactions that occurred during epoxidation, coming from uncomplete epoxidation of eugenol, hydrolysis of epoxides, the presence of eugenol/m-CPBA adduct and, as in previous study, the presence of dimer. However both studies did not report the elaboration of any materials.…”

Section: Iv2f Phosphazene Spacermentioning

confidence: 86%

Eugenol, a developing asset in biobased epoxy resins

Caillol

Boutevin

Auvergne

2021

Polymer

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bisphenol A (BPA), bisphenol F (BPF), metachloroperbenzoïc acid (m-CPBA), Steric exclusion chromatography (SEC), nuclear magnetic resonance (NMR), Dichloromethane (DCM), Acetic anhydride (Ac2O)Mono glycidyl silyl etherated eugenol (GSE), diglycidylether of bisphenol A (DGEBA), hexahydrophtalic anhydride (HHPA), Methylhexahydrophthalic anhydride (MHHPA),2,4,6tris(diMethylaminomethyl)phenol (DMP), diglycidylether diphenolates n-pentyle (DGEDP-Pe), eugenol mono-glycidyl ether (GE), 2-ethyl-4methylimidazole (EMID), diepoxidized isoeugenol (Iso-eug), diepoxidized eugenol (Eug), maleopimaric acid (MPA), isophoronediamine (IPDA), diglycidyl benzyl bis-eugenol (DEU-EP), diglycidyl butyl bis-eugenol (Eu-EP), 3,3'-Diaminodiphenylsulfone (33DDS), N,N-Dimethylacetamide (DMAc), N,N-diméthylpyridin-4-amine (DMAP), 4,4′-methylenedianiline (DDM), m-xylylenediamine (MXDA), hexachlorocyclotriphosphazene (HCP), Matrix Assisted Laser Desorption Ionisation/Time Of Flight (Maldi-TOF), hexachlorocyclotriphosphazene (HCP).

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Epoxy oligomers based on eugenol cyclotriphosphazene derivatives

Cited by 25 publications

References 7 publications

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

Eugenol, a developing asset in biobased epoxy resins

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