Synthesis and Behavior of Hexamethylenetetramine-Based Ionic Liquids as an Active Ingredient in Latent Curing Formulations with Ethylene Glycol for DGEBA

Zielinski, Dawid; Szpecht, Andrea; Hinc, Paulina; Śmiglak, Marcin

doi:10.3390/molecules28020892

Cited by 5 publications

(3 citation statements)

References 49 publications

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“…(Figure ). Following that work, several other groups reported the decomposition studies of HMTA under acidic and thermal conditions. , Recently, Grimblat and co-workers reported the thermal decomposition of HMTA and showed the formation of iminium and N -methyl iminium compounds as the products (Figure ). HMTA and its substituted analogues are used as reagents and reactants in chemical synthesis.…”

Section: Introductionmentioning

confidence: 93%

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Ruthenium-Induced Decomposition of Hexamethylenetetramine as a Tool for the Acid-Free Sommelet Reaction in Aqueous Medium

Devi,

Ghule,

Muthaiah

2024

J. Org. Chem.

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Hexamethylenetetramine (HMTA) is one of the most versatile and most utilized nitrogen-containing heterocyclic compounds in academia and industry. Most of the reactions involving HMTA employ stoichiometric or excess amounts of acid, which hamper the sustainability of the reactions. Herein, we report the first example of the ruthenium-mediated decomposition of HMTA at room temperature, supported by a detailed mechanistic study using thermogravimetric analysis/differential thermal analysis, variable-temperature NMR, UV−vis spectroscopy, and density functional theory techniques. The mechanism study also involves a comparison of the decomposition of HMTA, protonated HMTA, [RuCl 3 (HMTA)], and [FeCl 3 (HMTA)], which revealed that [RuCl 3 (HMTA)] decomposes at the lowest temperature and has the lowest HOMO−LUMO band gap of 2.66 eV. The ruthenium-induced decomposition of HMTA is successfully used as a tool to increase the sustainability of the Sommelet reaction as it employs simple RuCl 3 •nH 2 O as a catalyst in as low as 0.5 mol % concentration in aqueous medium. The developed methodology is found to be very selective and efficient even for the very challenging substrates, namely, aliphatic aldehydes and substrates with electron-withdrawing substituents. The findings of this work are the first of its kind in which ruthenium is employed in the Sommelet reaction and also provide a possible platform to improve the sustainability of all reactions involving HMTA as a reactant/reagent.

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Section: Introductionmentioning

confidence: 93%

“…Thermal- or acid-induced decomposition of HMTA (1) leads to the formation of products such as NH 3 , H 2 , HCN, CH 3 NH 2 , CH 3 CN, CH 4 , and N 2 in the absence of oxygen and HCHO, CO, NO, H 2 O, and CO 2 in the presence of oxygen (Figure ). − …”

Section: Introductionmentioning

confidence: 99%

Ruthenium-Induced Decomposition of Hexamethylenetetramine as a Tool for the Acid-Free Sommelet Reaction in Aqueous Medium

Devi,

Ghule,

Muthaiah

2024

J. Org. Chem.

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“…ILs have a number of advantages for use in composite materials and resin systems themselves. One of their most important properties is their ability to initiate the polymerization process of the epoxy resin [5,31,32]. ILs can be designed to predict their performance as cure initiators in a selected range of temperatures and intensities.…”

Section: Introductionmentioning

confidence: 99%

Multifunctional Modifying Systems Based on Ionic Liquids for Epoxy Resin Systems and Composites

Zielinski,

Szpecht,

Pomázi

et al. 2023

Applied Sciences

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The continuous development of the industry of composite materials and epoxy resins requires the development of components that modify these systems. It is extremely beneficial to modify functionality by using one or two substances instead of modifying only one system parameter. Typically, this end-use will determine the key parameters of the resin system that should be modified and the modification systems designed as such. In this study, we introduce novel systems utilizing ionic liquids, strategically designed to concurrently alter multiple system parameters, including: (i) flexibility, (ii) crosslinking density, and (iii) fire resistance. The following techniques were used in the research: (i) Differential Scanning Calorimetry (DSC), (ii) Thermogravimetric Analysis (TGA), (iii) Dynamic Mechanical Analysis (DMA) and (iv) fire performance tests (UL-94, Limiting Oxygen Index and Mass loss type cone calorimetry (MLC)) to show as much dependence of material parameters on the type of modifying additive as possible. Both the cured resin and the curing process as well as a single-layer composite reinforced with carbon fiber were tested. The results show that properly designed ionic liquids are able to perform many functions in the composite material and simultaneously affect several parameters, both by lowering and increasing them. In addition, they can exhibit activity in the field of flame-retardant composites.

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Supported Ionic Liquid‐Phase Materials (SILP) as a Multifunctional Group of Highly Stable Modifiers and Hardeners for Carbon and Flax Epoxy Composites

Zielinski,

Szpecht,

Kukawka

et al. 2024

ChemPlusChem

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This paper introduces a novel approach to enhance epoxy resin formulations by using SILP materials as multifunctional hardeners and fillers in composite structures reinforced with carbon and flax fibers. This study explores the integration of ionic liquids (ILs) onto a silica support structure, presenting various permutations involving silica selection, ionic liquid choice, and concentration. The focus of this study was to elucidate the influence of SILP on resin curing ability and the mechanical properties of the resulting composites. Detailed research was conducted, including Brunauer‐Emmett‐Teller analysis (BET) for SILP materials and curing characterization for epoxy resin formulations with different SILP materials. Furthermore, the mechanical properties of the obtained composites were determined by Scanning Electron Microscopy analysis (SEM) (the force at break, the maximum elongation at break, tensile strength, and modulus of elasticity). Through SILP incorporation, the mechanical properties of composites, including the modulus of elasticity and tensile strength, are substantially improved, a phenomenon akin to traditional filler effects. The findings highlight SILP materials as prospective candidates for concurrent hardening and filling roles within composites (through a single‐step procedure, with prolonged storage stability and controlled processing conditions), particularly pertinent as the composite industry veers toward epoxy bioresins necessitating liquefaction via temperature application.

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Synthesis and Behavior of Hexamethylenetetramine-Based Ionic Liquids as an Active Ingredient in Latent Curing Formulations with Ethylene Glycol for DGEBA

Cited by 5 publications

References 49 publications

Ruthenium-Induced Decomposition of Hexamethylenetetramine as a Tool for the Acid-Free Sommelet Reaction in Aqueous Medium

Ruthenium-Induced Decomposition of Hexamethylenetetramine as a Tool for the Acid-Free Sommelet Reaction in Aqueous Medium

Multifunctional Modifying Systems Based on Ionic Liquids for Epoxy Resin Systems and Composites

Supported Ionic Liquid‐Phase Materials (SILP) as a Multifunctional Group of Highly Stable Modifiers and Hardeners for Carbon and Flax Epoxy Composites

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