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Application of Quaternary Ammonium and Sulfonium Compounds

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Materials Chemistry".

Deadline for manuscript submissions: closed (30 September 2020) | Viewed by 6021

Special Issue Editor


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Guest Editor
University of Groningen, Groningen, The Netherlands
Interests: biomedical materials; biomedical coatings; hyperbranched polymers and the corresponding monomers; polyurethanes, polyurea; blocked isocyanates; degradable polymers; coupling agents; immobilization of coatings; antibacterial surfaces; hydrophobic surfaces; hydrophilic surface; lubricious surfaces

Special Issue Information

Dear Colleagues,

This Special Issue of Molecules encompasses the preparation and application of quaternary ammonium compounds (QACs). Quaternary ammonium compounds are a versatile group of compounds, which are broadly applicable. They are, in general, easy to prepare, making them very attractive from an economical point of view. Although at first glance, QACs look like very simple compounds, their possible structural compositions are nearly unlimited. The alkyl moiety connected to the nitrogen atom can be linear, aromatic, or cyclic, as well as a have varying number of nitrogen atoms per molecule. A general feature of useful QACs is that they carry a positive charge and a hydrophobic moiety. Amines are in an aqueous environment, highly protonated at a pH of ≤7. However, these protonated QACs and compounds with only short alkyl chains do not, in general, have the special properties that are desired. The interesting properties for nearly all of the applications appear when at least one of the alkyl chains is C6 or longer. In some respects, phosphonium and sulfonium compounds may have advantages over QACs, but they are more difficult (expensive) to prepare in the same abundant amounts of structural compositions as can be achieved with QACs.

QACs have a long history and have already been for about 100 years (first introduced in 1917). The main areas of use are in medical applications, cosmetics and disinfectants, and as surfactants and (ionic) solvents. QACs are very potent biocidal compounds, effective against bacteria, viruses, and fungi, while other disinfectants (e.g., phenolics, iodophors) are often less operative. QACs kill bacterial by destroying the cytoplasmic membrane, but do not interfere in the proliferation process, as antibiotics do. This makes them less susceptible to build-up resistance. Although QACs are not toxic chemicals, they are not harmless for the human body, but are nevertheless indispensable for combating infections. Because of the increasing resistance of bacteria against antibiotics (e.g., MRSA and VRSA) this biocidal behaviour becomes even more important. In addition, antibiotics are, unfortunately, not considered as blockbusters by the pharmaceutical industry. Phase transfer catalysts and surfactants make abundant use of the intrinsic amphiphilic character of QACs, in order to bridge the difference of the surface energy of water and organic compounds. Interestingly, some other QACs in a neat state have (such as salts) such a low melting that they are liquids at room temperature, and are applicable as highly polar solvents. One of the advantages is that their low vapor pressure (high boiling point) makes them suitable solvents under a high vacuum. In summary, quaternary ammonium compounds have excellent properties in many different fields.

This Special Issue aims to cover the recent progress and trends in the utilization of quaternary ammonium compounds and quaternary ammonium comprising polymers. Submissions are welcome to the list below, but are not limited to these topics. Types of contributions to this Special Issue can be full research articles, short communications, and reviews focusing on the preparation of quaternary ammonium compounds and quaternary ammonium comprising polymers, and their use in a variety of applications.

Prof. Ton J. A. Loontjens
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Antibacterial materials
  • Disinfectants
  • Cleaning
  • Cosmetics
  • Medicines
  • Drug carriers
  • Phospholipids (cell composition)
  • Phase transfer catalyst
  • Ionic liquids
  • Surfactant and emulsifier
  • Natural occurring compounds (e.g., lecitin)
  • Phosphonium and sulfonium compounds

Published Papers (2 papers)

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Research

11 pages, 7663 KiB  
Article
Surface Adsorption Properties and Layer Structures of Homogeneous Polyoxyethylene-Type Nonionic Surfactants in Quaternary-Ammonium-Salt-Type Amphiphilic Gemini Ionic Liquids with Oxygen- or Nitrogen-Containing Spacers
by Risa Kawai, Maiko Niki, Shiho Yada and Tomokazu Yoshimura
Molecules 2020, 25(21), 4881; https://doi.org/10.3390/molecules25214881 - 22 Oct 2020
Cited by 5 | Viewed by 2253
Abstract
The amphiphilic ionic liquids containing an alkyl chain in molecules form nano-structure in the bulk, although they also show surface activity and form aggregates in aqueous solutions. Although insights into the layer structures of ionic liquids were obtained using X-ray and neutron scattering [...] Read more.
The amphiphilic ionic liquids containing an alkyl chain in molecules form nano-structure in the bulk, although they also show surface activity and form aggregates in aqueous solutions. Although insights into the layer structures of ionic liquids were obtained using X-ray and neutron scattering techniques, the nanostructures of ionic liquids remain unclear. Herein, the surface adsorption and bulk properties of homogeneous polyoxyethylene (EO)-type nonionic surfactants (CxEO6; x = 8, 12, or 16) were elucidated in quaternary-ammonium-salt-type amphiphilic gemini ionic liquids with oxygen or nitrogen-containing spacers [2Cn(Spacer) NTf2; (Spacer) = (2-O-2), (2-O-2-O-2), (2-N-2), (2/2-N-2), (3), (5), or (6); n = 10, 12, or 14 for (2-O-2) and n = 12 for all other spacers] by surface tension, small- and wide-angle X-ray scattering, cryogenic transmission electron microscopy, and viscosity measurements. The surface tension of C12EO6 in 2Cn(Spacer) NTf2 with oxygen-containing spacers increased with increasing concentration of C12EO6, becoming close to that of C12EO6 alone, indicating that the amphiphilic ionic liquid adsorbed at the interface was replaced with CxEO6. In contrast, both 2Cn(Spacer) NTf2 with nitrogen-containing spacers and nonionic surfactants remained adsorbed at the interface at high concentrations. In the bulk, it was found that 2Cn(Spacer) NTf2 formed layer structures, in which the spacing depended on the alkyl chain length of CxEO6. These insights are expected to advance the practical applications of amphiphilic ionic liquids such as ion permeation, drug solubilization, and energy delivery systems. Full article
(This article belongs to the Special Issue Application of Quaternary Ammonium and Sulfonium Compounds)
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15 pages, 2865 KiB  
Article
Polymeric Coatings Based on Water-Soluble Trimethylammonium Copolymers for Antifouling Applications
by Artemis Tsagdi, Denisa Druvari, Dionisios Panagiotaras, Pavlos Avramidis, Vlasoula Bekiari and Joannis K. Kallitsis
Molecules 2020, 25(7), 1678; https://doi.org/10.3390/molecules25071678 - 6 Apr 2020
Cited by 11 | Viewed by 3056
Abstract
Crosslinked polymeric materials based on a quaternary trimethylammonium compound were developed and evaluated as potential antifouling coatings. For this purpose, two water-soluble random copolymers, poly(4-vinylbenzyltrimethylammonium chloride-co-acrylic acid) P(VBCTMAM-co-AAx) and poly(N,N-dimethylacrylamide-co-glycidylmethacrylate) P(DMAm-co-GMAx), were synthesized via free radical polymerization. A water based approach for the [...] Read more.
Crosslinked polymeric materials based on a quaternary trimethylammonium compound were developed and evaluated as potential antifouling coatings. For this purpose, two water-soluble random copolymers, poly(4-vinylbenzyltrimethylammonium chloride-co-acrylic acid) P(VBCTMAM-co-AAx) and poly(N,N-dimethylacrylamide-co-glycidylmethacrylate) P(DMAm-co-GMAx), were synthesized via free radical polymerization. A water based approach for the synthesis of P(VBCTMAM-co-AAx) copolymer was used. Coatings of the complementary reactive copolymers in different compositions were obtained by curing at 120 °C for one day and were used to coat aquaculture nets. These nets were evaluated in respect to their release rate using Total Organic Carbon (TOC) and Total Nitrogen (TN) measurements. Finally, the antifouling efficacy of these newly-composed durable coatings was investigated for 14 days in accelerated conditions. The results showed that this novel polymeric material provides contact-killing antifouling activity for a short time period, whereas it functions efficiently in biofouling removal after high-pressure cleaning. Full article
(This article belongs to the Special Issue Application of Quaternary Ammonium and Sulfonium Compounds)
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