Thermal study and evaluation of new menthol-based ionic liquids as polymeric additives

Andrade, Carlos Kleber Z.; Matos, Ricardo Alexandre F.; Oliveira, Viviane Bastos de; Durães, Jussara A.; Sales, Maria J. A.

doi:10.1007/s10973-009-0203-4

Cited by 16 publications

(8 citation statements)

References 14 publications

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“…Those isoprene derivatives are ideal naturally renewable materials for IL design and synthesis from the viewpoints of both environmental and bioapplication concerns. Surprisingly, the applications of terpene-based ILs mainly concern asymmetric catalysis in which optically active salts are added as chiral reaction media and/or catalysts − and other applications of such chiral ILs are mainly due to the presence of the optically active centers. − Unexpectedly, strongly biologically active terpene-based IL fragments are seldom utilized. These types of salts possess excellent antimicrobial properties, , are effective wood preservatives, might strongly activate, and stabilize enzymes, and/or even act as fragrance delivery systems …”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids with Natural Origin Component: A Path to New Plant Protection Products

Feder‐Kubis

Czerwoniec

Lewandowski

et al. 2019

ACS Sustainable Chem. Eng.

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One of the major problems in environmental industries is plant protection using ecologically and human friendly plant resistance inducers. To address this problem in an advantageous way, we used plant sources and substance that is responsible for plant resistance induction as the starting materials to synthesize new ionic liquids (ILs). Engineered ammonium and imidazolium salts with excellent yields of ≥98% were obtained under mild process conditions, using the (−)-menthol moiety, which is economically viable, widely used in many industries, and easily available from natural origins. This monoterpene alcohol, derived from renewable raw resources, was introduced to the cation part of the synthesized ILs. As a counterion, benzo[1.2.3]thiadiazole-7-carboxylate, which has resistance induction properties in plants, was introduced. In this study, we demonstrated that the careful design of IL’s cations and anions leads to new dual function compounds. This biological property manifests itself as a high level of antimicrobiological activity of the obtained salts, which allows new compounds to be concurrently classified as antimicrobial agents and at the same time as plant resistance inducers. Tested ammonium and imidazolium ILs exhibited antimicrobial activities higher than benzalkonium chloride, which is commonly used in biocides. When analyzing ILs, it was noted that the length of the alkyl chain, presence of the naturally occurring substituent, type of anion, type of cation core, and steric hindrance of the cyclic group are the principal factors determining antimicrobial properties. Work presented in this article shows one of the possibilities of enhancing biological properties, such as resistance induction, of the ILs, by pairing them in a sustainable manner with the antibiocidal agent to form bifunctional salts. Using this approach, it is possible to prepare bifunctional salts that maintain their systemic acquired resistance induction activity at very high levels, enhance solubility in water owing to their ionic characteristics, and deliver additional activities, such as antibacterial. Our design strategy indicates that the choice of the IL components can result in antimicrobial SAR plant resistance inducers, which might be successfully applied as disinfectants or plant resistance inducers.

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Section: Introductionmentioning

confidence: 99%

Ionic Liquids with Natural Origin Component: A Path to New Plant Protection Products

Feder‐Kubis

Czerwoniec

Lewandowski

et al. 2019

ACS Sustainable Chem. Eng.

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“…In order to further improve its characteristics, research has been performed with the addition of different substances to this polymer. [1,2] Recently, ionic liquids (ILs) have been studied as additives for polymers. Studies report, among other applications, the performance of ILs as solvents for polymerization, modifiers of spectroscopic properties and their addition to provide conductivity to polymers.…”

Section: Introductionmentioning

confidence: 99%

“…BMIM.BF 4 and BMIM.PF 6 were chosen for being commercially available and widely used as a reaction media and the menthol-based chiral ILs were chosen in view of our earlier studies about their properties as polymeric additives. [2] Experimental Part Synthesis of ILs BMIM.BF 4 and BMIM.PF 6 were synthesized in two steps. The first involved to the alkylation of N-methylimidazolium with 10 equivalents of butyl iodide, producing 1-butyl-3-methylimidazolium (BMIM.I), as a viscous reddish liquid (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…Poly(methyl methacrylate) (PMMA) is used mainly on billboards, signs and in the manufacture of lenses due to its similarity to glass and its optical characteristics. In order to further improve its characteristics, research has been performed with the addition of different substances to this polymer 1, 2. Recently, ionic liquids (ILs) have been studied as additives for polymers.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, the objective of this study is to investigate the influence of the ILs 1‐butil‐3‐methylimidazolium tetrafluoroborate (BMIM.BF 4 ), 1‐butyl‐3‐methylimidazolium hexafluorophosphate (BMIM.PF 6 ) (Figure 1a), acetyl‐(−)‐menthol‐1‐butylimidazolium tetrafluoroborate ([amebim]BF 4 ) and acetyl‐(−)menthol‐1‐buthylimidazole hexafluorophosphate ([amembim]PF 6 ) (Figure 1b) on the spectroscopic properties of PMMA. BMIM.BF 4 and BMIM.PF 6 were chosen for being commercially available and widely used as a reaction media and the menthol‐based chiral ILs were chosen in view of our earlier studies about their properties as polymeric additives 2…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of Spectroscopic and Morphological Properties of PMMA Modified with ILs

Oliveira

Pereira

Andrade

et al. 2012

Macromolecular Symposia

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In recent years, an important class of new compounds, ionic liquids (ILs), has been investigated as additives for polymers. In this work, we carried out the synthesis of 4 different ILs: 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM.BF 4 ), 1-butyl-3-methylimidazolium hexafluorophosphate (BMIM.PF 6 ), and the chiral ILs acetyl-(À)menthol-1-buthylimidazole tetrafluoroborate ([amebim]BF 4 ) and acetyl-(À)menthol-1-buthylimidazole hexafluorophosphate ([amebim]PF 6 ). These ILs were added to poly(methyl methacrylate) (PMMA) in 10, 20 and 30% ratios by weight and the ILs, PMMA and the obtained materials (PMMA:ILs) were characterized by infrared, visible spectroscopy and atomic force microscope. The ILs added to PMMA did not provide significant changes in the infrared spectra, compared to pure PMMA. However, the absorption spectra in the visible region of the PMMA:ILs materials showed differences, compared to the spectrum of pure PMMA.

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Artificial Neural Network and Response Surface Methodology Modelling of Surface Tension of 1-Butyl-3-methylimidazolium Bromide Solution

Soman

Kalaichelvi

Radhakrishnan

2018

Communications in Computer and Information Science

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Thermal study and evaluation of new menthol-based ionic liquids as polymeric additives

Cited by 16 publications

References 14 publications

Ionic Liquids with Natural Origin Component: A Path to New Plant Protection Products

Ionic Liquids with Natural Origin Component: A Path to New Plant Protection Products

Evaluation of Spectroscopic and Morphological Properties of PMMA Modified with ILs

Artificial Neural Network and Response Surface Methodology Modelling of Surface Tension of 1-Butyl-3-methylimidazolium Bromide Solution

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