Impact of aliphatic amine comonomers on DGEBA epoxy network properties

Amaral, Camila Rodrigues; Rodríguez, Rubén Jesus Sánchez; García, Filiberto González; Júnior, Lima; Carvalho, Eduardo Atem de

doi:10.1002/pen.23751

Cited by 23 publications

(11 citation statements)

References 30 publications

(25 reference statements)

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“…The tan δ peak provides important information about the cured epoxy networks. Typically, a higher tan δ peak represents improved fracture toughness. , Clearly, EDV/IPDA networks exhibited a notably higher peak (Figure b, solid red) than did other three networks. The width of tan δ reflects the sample homogeneity; the sharper and narrower the peak, the more homogeneous the sample .…”

Section: Resultsmentioning

confidence: 95%

Biobased Divanillin As a Precursor for Formulating Biobased Epoxy Resin

Fang

Nikafshar

Hegg

et al. 2020

ACS Sustainable Chem. Eng.

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Divanillin (DV), which can be facilely synthesized via vanillin dimerization, was employed as a building block to formulate epoxy resin. DV was synthesized through a novel approach in hot water in only 30 min with a yield of 87.5%. The process involved FeSO4-catalyzed Na2S2O8-based oxidative coupling of vanillin without any purification, followed by treatment with biobased epichlorohydrin. Epoxidized-divanillin (EDV) was cured with the petroleum-based, commercially available hardener isophorone diamine (IPDA) and a biobased-diamine (GX-3090). Complete curing of the mixture was confirmed by Fourier transform infrared (FTIR) spectroscopy and statistical heat resistant-indices (Ts), which indicated the formation of cross-linked networks with a thermostability similar to materials prepared with diglycidyl ether bisphenol A (DGEBA, the commercial BPA-based resin). The epoxy resin developed with this new formulation had comparable storage moduli (1.7–2.3 GPa) and similar glass transition temperatures as commercial resins. The epoxy networks exhibited good solvent resistance, while the presence of aldehyde groups in EDV yielded in more readily cleavable ester and amide bonds during the cross-linking process, yielding a resin with improved degradation under acidic conditions. Almost 40% of the segments in networks cured with EDV/IPDA were solubilized in acetone after treatment with 1 M HCl at room temperature in 24 h.

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Section: Resultsmentioning

confidence: 95%

Biobased Divanillin As a Precursor for Formulating Biobased Epoxy Resin

Fang

Nikafshar

Hegg

et al. 2020

ACS Sustainable Chem. Eng.

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“…As shown in Table 2 , the yield strength of the system with a degree of cross-linking of 85.4% was close to other simulation results and experimental values. The results were calculated at 300 K with average rate of 2.4 × 10 8 s −1 in this work and the experiment value was measured at strain rates from 5.7 × 10 −4 to 8.3 × 10 −3 s −1 [ 53 , 54 , 55 ].…”

Section: Resultsmentioning

confidence: 99%

Molecular Dynamics Investigation of the Thermo-Mechanical Properties of the Moisture Invaded and Cross-Linked Epoxy System

Sheng

Sun

et al. 2021

Polymers

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In spite of a high market share of plastic IC packaging, there are still reliability issues, especially for the effects of moisture. The mechanism between moisture and epoxy polymer is still obscure. A multi-step cross-linking approach was used to mimic the cross-linking process between the DGEBA resin and JEFFAMINE®-D230 agent. Based on the molecular dynamics method, the thermo-mechanical properties and microstructure of epoxy polymer were analyzed. In this paper, the degree of cross-linking ranged from 0% to 85.4% and the moisture concentration ranged from 0 wt.% to 12 wt.%. The hydrogen bonds were investigated in the moisture invaded epoxy polymer. Although most of the hydrogen bonds were related to water molecules, the hydrogen bonds between the inside of epoxy polymer were reduced only a little as the concentration of moisture increased. The diffusion coefficient of the water molecules was found to increase with the increase of moisture concentration. When the moisture concentration was larger than 12 wt.% or smaller than 1.6 wt.%, the diffusion coefficient was less affected by the epoxy polymer. In addition, the free volume and the thermal conductivity of the epoxy polymer were considered. It was found that the moisture could increase the thermal conductivity from 0.24 to 0.31 W/m/K, identifying a coupling relationship between moisture and thermal properties. Finally, the mechanical properties of epoxy polymer were analyzed by uniaxial tensile simulation. The COMPASS and DREIDING force fields were used during the uniaxial tensile simulation. A better result was achieved from the DREIDING force field compared with the experiment. The degree of cross-linking was positively correlated with mechanical properties. For the system with the largest degree of cross-linking of 85.4%, the Young’s modulus was 2.134 ± 0.522 GPa and the yield strength was 0.081 ± 0.01 GPa. There were both plasticizing and anti-plasticizing effects when the water molecules entered the epoxy polymer. Both the Young’s moduli and yield strength varied in a large range from 1.38 to 2.344 GPa and from 0.062 to 0.128 GPa, respectively.

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“…Overall the molecular weights between crosslinks are high when compared to molecular weights of epoxy resins determined by other methods (30,31). While the molecular weights are higher than other reported methods the shear parallel plate rheometer represents a method to explore the network of a thermoset material that minimizes clamping effects.…”

Section: Dynamic Mechanical Analysis and Parallel Plate Oscillatory Rmentioning

confidence: 86%

Bio-Based Epoxy Resins from Diphenolate Esters—Replacing the Diglycidyl Ether of Bisphenol A

Maiorana

Spinella

Gross

2015

ACS Symposium Series

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Bio-based epoxy monomers were synthesized from diphenolic acid (DPA) with the goal of producing a drop-in replacement for the diglycidyl ether of bisphenol A (DGEBA). A series of resins was prepared from alkyl diphenolate esters. The purity and properties of the resins were investigated through 1 H NMR and mass spectrometry, rheology, and differential scanning calorimetry.The bio-based resins were cured under identical conditions using the same crosslinker and the thermomechanical properties were compared by dynamic mechanical analysis (DMA), tensile testing, parallel plate rheology, and thermogravimetric analysis.The thermal properties of the diphenolate epoxy resins were tunable through the length of the ester chain.

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Impact of aliphatic amine comonomers on DGEBA epoxy network properties

Cited by 23 publications

References 30 publications

Biobased Divanillin As a Precursor for Formulating Biobased Epoxy Resin

Biobased Divanillin As a Precursor for Formulating Biobased Epoxy Resin

Molecular Dynamics Investigation of the Thermo-Mechanical Properties of the Moisture Invaded and Cross-Linked Epoxy System

Bio-Based Epoxy Resins from Diphenolate Esters—Replacing the Diglycidyl Ether of Bisphenol A

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