Reactions of DGEBA epoxy cured with diethanolamine: Isoconversional kinetics and implications to network structure

McCoy, John D.; Ancipink, Windy; Maestas, Salomon; Draelos, Lara R.; Devries, David; Kropka, Jamie Michael

doi:10.1016/j.tca.2018.11.013

Cited by 14 publications

(8 citation statements)

References 38 publications

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“…Due the absence of active hydrogen on tertiary amine structure, this latter cannot take part to the epoxy-amine polyaddition but can act as catalyst, resulting in the acceleration of the epoxy-amine curing. 73 Tertiary amines are indeed a really important class of accelerators or co-curing agents for phenol, acid anhydride, polyamide and polyamine curing agents. 7,74 Due to an anionic mechanism, tertiary amine formed during the epoxy-amine curing could also catalyze the homopolymerization reaction between the secondary alcohols with epoxy groups, which is actually a really slow reaction.…”

Section: Catalytic Effect Of the Tertiary Aminementioning

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: Catalytic Effect Of the Tertiary Aminementioning

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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“…The reason could be ascribed to the destruction of a stable structure of zein affected by the hydroxyl generated from the ring-opening reaction with EGDE and DEA. Compared to raw zein, the thermal degradation peak in the DTG curves became broader, while forming Zein-EGDE and Zein-EGDE/DEA, and such a thermostability change could be the result of the accidental cross-linking reaction of small partial EGDE with zein to form a more solid structure, , and the DTG curve for Zein-EGDE/DEA even splits into a new shoulder decomposition peak centered at 393 °C, owing to the existence of bonds between epoxy from EGDE and amine from DEA. − …”

Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Zein-Based Nanoparticles via Ring-Opening Reaction and Self-Assembly as Aqueous Nanocarriers for Pesticides

Lin

Wang

et al. 2020

J. Agric. Food Chem.

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Herein, we prepared and compared two water-soluble amphiphilic zein-based nanocarrier systems with avermectin (AVM) payload to enhance pesticide's water-dispersity, foliage wettability, adhesion, anti-UV, and pH-responsive controlled release property. Ethylene glycol diglycidyl ether (EGDE) and diethanolamine (DEA) were utilized to conjugate with hydrophobic zein via a ring-opening reaction and then encapsulated with AVM via a hydrophobic interaction to fabricate a nanopesticide marked as AVM@Zein-EGDE/DEA. For the sake of further improving the nanocarrier's performance, sodium carboxymethyl cellulose (CMC) was grafted with methyl methacrylate (MMA) and 2-hydroxyethyl methacrylate (HEMA) to form a kind of copolymer CMC-g-P(HEMA-MMA), which was applied to conjugate with Zein-EGDE via a ring-opening reaction. Likewise, another nanopesticide system named AVM@Zein-EGDE/CMC-g-P(HEMA-MMA) was obtained through hydrophobic interactions as well as the electrostatic effect. Various techniques were utilized to confirm chemical interaction, thermal behavior, structural characteristics, and stability. The results showed that AVM encapsulated in Zein-EGDE/CMC-g-P(HEMA-MMA) possessed a larger particle size with an average value of 180−254 nm than AVM loaded in Zein-EGDE/DEA with 144−175 nm but had better stability in aqueous solution. Also, AVM loaded in Zein-EGDE/CMC-g-P(HEMA-MMA) enhanced the encapsulation efficiency, and both of them exhibited excellent pH-responsive sustained release behavior. Besides, the former improved wettability on a cucumber leaf surface and enhanced adhesion ability compared to AVM@Zein-EGDE/DEA because of CMC-g-P(HEMA-MMA) with hydrophobic segments. Similarly, anti-UV performance was also enhanced owing to CMC-g-P(HEMA-MMA) as an additional protective layer. More importantly, the encapsulation of Zein-EGDE/DEA and Zein-EGDE/CMC-g-P(HEMA-MMA) as protective barriers for AVM still retained a similar toxicity level. Overall, we demonstrated the proof of concept for the application of amphiphilic zeinbased nanomaterials as aqueous nanocarriers for hydrophobic pesticides.

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“…Previous work by Kropka et al focused on the reaction kinetics of epoxy monomers with diethanolamine as the hydroxyl donor. 22 With high concentrations of the hydroxyl components, proton transfer is possible and the alkoxide is transferred away from the polymer chain to small molecules (Scheme 1c, pathway iv), resulting in the formation of many small network clusters compared to few high molecular weight clusters in the anionic chain-growth Scheme 1. Proposed Mechanisms for the Nucleophilic Attack a a (a) 1-Unsubstitued and (b) 1-substitued imidazoles toward epoxy monomers with the formation of (1:1) and (1:2) adducts that initiate the polymerization via the alkoxide ion.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Furthermore, hyperbranched additives led to increased toughness of the materials. Previous work by Kropka et al focused on the reaction kinetics of epoxy monomers with diethanolamine as the hydroxyl donor . With high concentrations of the hydroxyl components, proton transfer is possible and the alkoxide is transferred away from the polymer chain to small molecules (Scheme c, pathway iv), resulting in the formation of many small network clusters compared to few high molecular weight clusters in the anionic chain-growth polymerization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Homogeneous Epoxy Networks: Development of a Sustainable Material Platform Using Epoxy-Alcohol Polyaddition

Fantoni

Koch

Baudis

et al. 2022

ACS Appl. Polym. Mater.

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The development of bio-based epoxy resins from aliphatic biomass and lignin has rapidly increased over the past few decades. While thermal curing of such monomers with polyfunctional amines and anhydrides has been intensively discussed in literature, surprisingly, their polymerization behavior using alcohols as co-curing agents and the resulting mechanical properties have not been investigated in detail up to now. Herein, the polymerization mode of bio-based epoxides with alcohols using imidazoles as catalysts was studied via 1H-NMR analysis, revealing a controlled alternating co-polymerization between difunctional epoxy and alcohol monomers. Furthermore, differential scanning calorimetry analysis was used to obtain the theoretical heat of polymerization (∼100 kJ mol–1) of multifunctional monomers and the formulations exhibited high storage stabilities of up to 28 days. By varying the core structure and functionality of the epoxy monomers, high-performance thermosets with a tunable T G (0–110 °C) and high tensile toughness of up to 18 MJ m–3 were obtained. These performances show potential for the application of bio-based epoxy networks as coatings for key industrial sections such as automotive technologies.

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Reactions of DGEBA epoxy cured with diethanolamine: Isoconversional kinetics and implications to network structure

Cited by 14 publications

References 38 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

Preparation and Characterization of Zein-Based Nanoparticles via Ring-Opening Reaction and Self-Assembly as Aqueous Nanocarriers for Pesticides

Synthesis and Characterization of Homogeneous Epoxy Networks: Development of a Sustainable Material Platform Using Epoxy-Alcohol Polyaddition

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