Development of amine-based latent accelerator for one-pot epoxy system with low curing temperature and high shelf life

Hesabi, Mohammadnabi; Salimi, Ali; Beheshty, Mohammad Hosain

doi:10.1016/j.eurpolymj.2018.10.044

Cited by 24 publications

(12 citation statements)

References 33 publications

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“…49 Accelerators are usually used for latent hardeners to reduce the curing temperature. 50 However, this summary of amine reactivity is an overall vision and the reality is more complexe by considering H bonds and inductive or mesomer effects induced by amine substituents. Some factors allow to modify the reactivity, such as the presence of heteroatom in the chain, allowing to form H bonds, or by adding moieties inducing inductive of mesomer effect.…”

Section: Reactivity Of Primary Amines Towards Epoxy Moietiesmentioning

confidence: 99%

A perspective approach on the amine reactivity and the hydrogen bonds effect on epoxy-amine systems

Mora

Tayouo

Boutevin

et al. 2020

European Polymer Journal

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Abbreviations: 3-cyclohexanedimethanamine (1,3-BAC), 2,5-bis[(2-oxiranylmethoxy)methyl]-benzene (BOB), 2,5-bis[(2-oxiranylmethoxy)-methyl]-furan (BOF), bisphenol A (BPA), 1,3-cyclohexanediamine (1,3-CHDA), carcinogenic, mutagenic and reprotoxic (CMR), 4,4'-diaminodiphenylmethane (DDM), density functional theory (DFT), diglycidyl ether of bisphenol A (DGEBA), dynamic mechanical analysis (DMA), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), high performance liquid chromatography (HPLC), isophoronediamine (IPDA), kinetic substitution effect (KSE), m-phenylenediamine (mPDA), m-xylylenediamine (MXDA), non-isocyanate polyurethane (NIPU), nuclear magnetic resonance (NMR), polyamide (PA), poly(εcaprolactone) (PCL), poly(diglycidyl ether of bisphenol A) (poly(DGEBA)), poly(ethylene oxide) (PEO), poly(methyl methacrylate) (PMMA), polyurethane (PU) size-exclusion (SEC), tetrafurane (THF), volatile organic compound (VOC).

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Section: Reactivity Of Primary Amines Towards Epoxy Moietiesmentioning

confidence: 99%

A perspective approach on the amine reactivity and the hydrogen bonds effect on epoxy-amine systems

Mora

Tayouo

Boutevin

et al. 2020

European Polymer Journal

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“…As the heating rate accelerated, the reaction of the active groups in the system intensified. The heat release of the system per unit time increased, thereby causing the DSC curve's peak value to increase with the heating rate 47 . Table 1 summarizes the data extracted from the DSC curves.…”

Section: Resultsmentioning

confidence: 99%

“…The heat release of the system per unit time increased, thereby causing the DSC curve's peak value to increase with the heating rate. 47 Table 1 summarizes the data extracted from the DSC curves. The table also lists the initial, peak, and final curing temperatures calculated by the extrapolation T-β method.…”

Section: Curing Kinetics Studiesmentioning

confidence: 99%

Synthesis and performance of flexible epoxy resin with long alkyl side chains via click reaction

Dai

Sui

et al. 2021

Journal of Polymer Science

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Epoxy resin is a thermosetting polymer with excellent performance and wide application. However, it suffers from low toughness and high brittleness because of its high crosslink density. To overcome these disadvantages, this study synthesizes a toughened, flexible, and hydrophobic epoxy resin (DGEBDBP) by introducing a flexible segment into the polymer network via a thiol-ene click reaction. The cured flexible epoxy resin is obtained by mixing E44, DGEBDBP, and polyamide curing agents of varying contents. The long alkyl side chains significantly improve the mechanical properties and hydrophobicity of the cured epoxy resin. The sample containing 75% DGEBDBP and 25% E44 achieve the highest breaking elongation that was nine times that of pure E44, the highest compressive strength of 112.8 MPa, and the highest contact angle of 101.4. The introduction of side chains through the thiol-ene click reaction can provide a simple and effective method for designing and preparing multifunctional epoxy resins.

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“…For one‐component liquid epoxy systems, the shelf life is usually assessed by measuring the changes in viscosity until it becomes double in value 28,29 . Besides, the pot life can also be evaluated by observing the changes in fluidity 13,14 or FT‐IR spectra 30 for different storage time. But as for the solid EPRS containing curing accelerators in this study, we employed DSC techniques to estimate the storage stability by monitoring the thermogram changes of samples stored at 30°C for different storage times with the heating rate of 10°C min −1 .…”

Section: Resultsmentioning

confidence: 99%

Imidazole derivative with an intramolecular hydrogen bond as thermal latent curing accelerator for epoxy/phenolic resins

Wei

Gou

Sun

et al. 2021

J of Applied Polymer Sci

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One‐component epoxy systems with long shelf life during storage or transportation, while high curing reactivity during molding as well as satisfactory mechanical and thermal performances after curing, are extremely essential for industrial application. Herein, we used salicylaldehyde and o‐phenylenediamine to synthesize 2‐(2′‐hydroxyphenyl)‐1H‐benzimidazole (HPBI), an imidazole derivative with an intramolecular hydrogen bond between the phenolic hydroxyl group and the pyridine‐type nitrogen atom of imidazole ring, and further employed HPBI as a thermal latent curing accelerator for epoxy/phenolic resins. The intramolecular hydrogen bond endowed HPBI with inert activity toward resins at room temperature, making the one‐component resin system a long‐term storage stability (21 days of shelf life at 30°C). Once rising the temperature to a high degree, a rather high activity of HPBI to accelerate the curing process of epoxy/phenolic resins. It was attributed to the effective release of high activity of the pyridine‐type nitrogen by breaking the intramolecular hydrogen bond at high temperature. In addition, the resulted thermosets from HPBI also possessed the comparable Tg (>130°C, determined by DMA) and thermostability (Td‐5% > 380°C) with that from common curing accelerators. Therefore, HPBI was proved to be a promising thermal latent curing accelerator applied in electronic packaging field.

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Development of amine-based latent accelerator for one-pot epoxy system with low curing temperature and high shelf life

Cited by 24 publications

References 33 publications

A perspective approach on the amine reactivity and the hydrogen bonds effect on epoxy-amine systems

A perspective approach on the amine reactivity and the hydrogen bonds effect on epoxy-amine systems

Synthesis and performance of flexible epoxy resin with long alkyl side chains via click reaction

Imidazole derivative with an intramolecular hydrogen bond as thermal latent curing accelerator for epoxy/phenolic resins

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