Fig 1 - uploaded by Yudovin-Farber Ira
Content may be subject to copyright.
Source publication
Quaternary ammonium polyethyleneimine (QA-PEI)-based nanoparticles were synthesized by crosslinking with dibromopentane followed
by N-alkylation with various alkyl halides and further N-methylation with methyl iodide. Insoluble pyridinium-type particles
were prepared by suspension polymerization of 4-vinyl pyridine followed by N-alkylation with alk...
Citations
... In addition, The DCs of 20(QA10+TMXDI) p and 20(QA12+TMXDI) p were higher than 0.55, which is recommended for clinical applications [57]. Thus, we can conclude that polymerization of 20(QA10+TMXDI) m and 20(QA12+TMXDI) m exhibited high efficiency and was not negatively influenced by a central benzene ring (which increases system stiffness [54]) and N-alkyl substituents (which increase the distance between polymerizing species [58,59]) present in their molecules. ...
In this study, two novel quaternary ammonium urethane-dimethacrylates (QAUDMAs) were designed for potential use as comonomers in antibacterial dental composite restorative materials. QAUDMAs were synthesized via the reaction of 1,3-bis(1-isocyanato-1-methylethyl)benzene with 2-(methacryloyloxy)ethyl-2-decylhydroxyethylmethylammonium bromide (QA10+TMXDI) and 2-(methacryloyloxy)ethyl-2-dodecylhydroxyethylmethylammonium bromide (QA12+TMXDI). Their compositions with common dental dimethacrylates comprising QAUDMA 20 wt.%, urethane-dimethacrylate monomer (UDMA) 20 wt.%, bisphenol A glycerolate dimethacrylate (Bis-GMA) 40 wt.%, and triethylene glycol dimethacrylate (TEGDMA) 20 wt.%, were photocured. The achieved copolymers were characterized for their physicochemical and mechanical properties, including their degree of conversion (DC), glass transition temperature (Tg), polymerization shrinkage (S), water contact angle (WCA), flexural modulus (E), flexural strength (FS), hardness (HB), water sorption (WS), and water leachability (WL). The antibacterial activity of the copolymers was characterized by the minimum bactericidal concentration (MBC) and minimum inhibitory concentration (MIC) against Staphylococcus aureus and Escherichia coli. The achieved results were compared to the properties of a typical dental copolymer comprising UDMA 40 wt.%, Bis-GMA 40 wt.%, and TEGDMA 20 wt.%. The introduction of QAUDMAs did not deteriorate physicochemical and mechanical properties. The WS and WL increased; however, they were still satisfactory. The copolymer comprising QA10+TMXDI showed a higher antibacterial effect than that comprising QA12+TMXDI and that of the reference copolymer.
... The antimicrobial activity of QA-PEI-NPs against standard Gram-positive (such as Staphylococcus aureus) and Gram-negative (such as Escherichia coli) strains and numerous other pathogenic bacteria strains has been proven 33-36 . It was also confirmed with diversified methodology that QA-PEI-NPs show activity against cariogenic bacteria Streptococcus mutans in in vitro tests [37][38][39][40] and even against intraoral biofilm during an in vivo experiment 41 . However, little is known about other consequences of using QA-PEI-NPs as additives to resin-composite materials, because only in few studies modified commercially available resin-composite materials were investigated. ...
... Beyth et al. 39 and Shvero et al. 38 found that commercially available flow and hybrid composites modified with 1% of QA-PEI-NPs present durable antibacterial activity against S. mutans in a direct contact test and strong activity during 24 h contact confirmed by SEM investigations. Similar results were obtained with an analogous methodology for additional modified commercial composites 37,40 . In these investigations, only formulations that contained 1% and 2% were tested. ...
A significant problem related to the functioning of resin-based composites for dental fillings is secondary or recurrent caries, which is the reason for the need for repeated treatment. The cross-linked quaternary ammonium polyethylenimine nanoparticles (QA-PEI-NPs) have been shown to be a promising antibacterial agent against different bacteria, including cariogenic ones. However, little is known about the properties of dental dimethacrylate polymer-based composites enriched with QA-PEI-NPs. This research was carried out on experimental composites based on bis-GMA/UDMA/TEGDMA matrix enriched with 0.5, 1, 1.5, 2 and 3 (wt%) QA-PEI-NPs and reinforced with two glass fillers. The cured composites were tested for their adherence of Streptococcus Mutans bacteria, cell viability (MTT assay) with 48 h and 10-days extracts , degree of conversion (DC), water sorption (WSO), and solubility (WSL), water contact angle (CA), flexural modulus (E), flexural strength (FS), compressive strength (CS), and Vickers microhardness (HV). The investigated materials have shown a complete reduction in bacteria adherence and satisfactory biocompatibility. The QA-PEI-NPs additive has no effect on the DC, VH, and E values. QA-PEI-NPs increased the CA (a favorable change), the WSO and WSL (unfavorable changes) and decreased flexural strength, and compressive strength (unfavorable changes). The changes mentioned were insignificant and acceptable for most composites, excluding the highest antibacterial filler content. Probably the reason for the deterioration of some properties was low compatibility between filler particles and the matrix; therefore, it is worth extending the research by surface modification of QA-PEI-NPs to achieve the optimum performance characteristics.
... Two new peaks at 1250 and 1700 cm À 1 were observed, which can be attributed to the vibration of CÀ O and C=O of PAEtMA, respectively. The apparent peak at 1,000 cm À 1 indicates the presence of quaternary ammonium groups, [24] that have strong electrostatic forces with water molecules in the atmosphere. ...
Atmospheric water harvesting (AWH) has been recognized as a next‐generation technology to alleviate water shortages in arid areas. However, the current AWH materials suffer from insufficient water adsorption capacity and high‐water retention, which hinder the practical application of AWH materials. In this study, we developed a novel dual‐layered hydrogel (DLH) composed of a light‐to‐heat conversion layer (LHL) containing novel polydopamine‐manganese nanoparticles (PDA−Mn NPs) and a water adsorption layer (WAL) made of 2‐(acryloyloxyethyl) trimethylammonium chloride (AEtMA). The WAL has a strong ability to adsorb water molecules in the air and has a high‐water storage capacity, and the PDA−Mn NPs embedded in the LHL have excellent photothermal conversion efficiency, leading to light‐induced autonomous water release. As a result, the DLH displays a high‐water adsorption capacity of 7.73 g g⁻¹ under optimal conditions and could near‐quantitatively release captured water within 4 h sunlight exposure. Coupled with its low cost, we believed that the DLH will be one of the promising AWH materials for practical applications.
... A new sharp peak appeared around 1648.84 cm -1 and was attributed to C-N stressing vibrations as a result of quaternization. The peak at around 2933.20 cm -1 shifted from 2977.55 cm -1 and its intensity increased due to increase of -C-H stressing vibrations as a result of the methyl groups attached to nitrogen during quaternization [24], [43]- [45]. Mwangi and co-authors observed similar cases in their research. ...
Fluorides are one of the many pollutants found in water. At low concentration, fluorides are essential for improving the density and hardness of bones and teeth enamel during their growth. A concentration greater than 1.5 mg/L in drinking water has several detrimental effects on human health, including dental and skeletal fluorosis. There are several methods employed to rid water of fluorides. These include, reverse osmosis, adsorption, ion exchange, coagulation and flocculation. This study focuses on removal of fluorides from aqueous solutions by coagulation using quaternary ammonium functionalized waste paper bio-coagulant. Quaternary ammonium compounds were synthesized from waste paper by first nitrating cellulose present in waste paper. The attached nitro groups, were reduced to amine groups and quaternization was done using methyl iodide. The prepared bio-coagulant was characterized using FTIR and TGA. The coagulant was used to remove fluorides from model solutions and real water samples from Gilgil area in Nakuru county, Kenya. A fluoride ISE was used to determine fluoride ion concentration in each model solution and in the real water samples. Optimized parameters included pH, initial fluoride ion concentration, contact time and bio-coagulant dosage. Characterization data confirmed successful quaternization was achieved. Thermal stability of the material was up to a temperature of 563.15 K. The optimum pH value was 4.0 while the contact time was 15 minutes. Fluoride removal increased with increase in initial concentration up to an optimum 20 mg/L. Fluoride removal was also observed to increase with increase in coagulant dosage. Obtained data fitted well on Langmuir adsorption isotherm with R 2 value of 0.9707, confirming chemisorption as the predominant intermediate process. An adsorption capacity of 3.6311 mg/g was obtained. Fluoride ion removal percentage in the model solution was 81% and 66.25% in the real water sample.
... The reduction in WS as the Cm increased can be explained by the increasing hydrophobicity of the longer N-alkyl chains [46]. It is also possible that the longer N-alkyl chains can shield the positively charged quaternary nitrogen ion, thus limiting its ability to absorb water [50]. ...
This study aimed to elucidate the physicochemical properties of copolymers comprising 40 wt.% bisphenol A glycerolate dimethacrylate (Bis-GMA), 40 wt.% quaternary ammonium urethane-dimethacrylate analogues (QAUDMA-m, where m corresponds to the number of carbon atoms in the N-alkyl substituent), and 20 wt.% triethylene glycol dimethacrylate (TEGDMA) copolymers (BG:QAm:TEGs). The BG:QAm:TEG liquid monomer compositions and reference compositions (40 wt.% Bis-GMA, 40 wt.% urethane-dimethacrylate (UDMA), 20 wt.% TEGDMA (BG:UD:TEG) and 60 wt.% Bis-GMA, 40 wt.% TEGDMA (BG:TEG)) were characterized in terms of their refractive index (RI) and monomer glass transition temperature (Tgm) and then photocured. The resulting copolymers were characterized in terms of the polymer glass transition temperature (Tgp), experimental polymerization shrinkage (Se), water contact angle (WCA), water sorption (WS), and water solubility (SL). The prepared BG:QAm:TEG liquid monomer compositions had RI in the range 1.4997–1.5129, and Tgm in the range −52.22 to −42.12 °C. The BG:QAm:TEG copolymers had Tgp ranging from 42.21 to 50.81 °C, Se ranging from 5.08 to 6.40%, WCA ranging from 81.41 to 99.53°, WS ranging from 25.94 to 68.27 µg/mm3, and SL ranging from 5.15 to 5.58 µg/mm3. Almost all of the developed BG:QAm:TEGs fulfilled the requirements for dental materials (except BG:QA8:TEG and BG:QA10:TEG, whose WS values exceeded the 40 µg/mm3 limit).
... The structure of polysiloxanes is characterized by good thermal, bio-, and chemical stability [8]. Ammonium salts have a wide range of activity against microorganisms, and they are also classified as surfactants [9][10][11]. These surfactants exhibit low critical micelle concentrations (CMC) in water, which arouses interest in treating soils and clays from contaminants [12]. ...
... It was found that the hydrophobicity of the QA:TEGs' surface, quantified by the water contact angle values, increased with the increase in the length of the N-alkyl substituent [27]. Third, there is also a hypothesis in the literature that long N-alkyl chains can adopt specific conformations that obscure the quaternary nitrogen atoms, reducing water affinity [46]. ...
The use of dental composites based on dimethacrylates that have quaternary ammonium groups is a promising solution in the field of antibacterial restorative materials. This study aimed to investigate the mechanical properties and behaviors in aqueous environments of a series of six copolymers (QA:TEG) comprising 60 wt.% quaternary ammonium urethane-dimethacrylate (QAUDMA) and 40 wt.% triethylene glycol dimethacrylate (TEGDMA); these copolymers are analogous to a common dental copolymer (BG:TEG), which comprises 60 wt.% bisphenol A glycerolate dimethacrylate (Bis-GMA) and 40 wt.% TEGDMA. Hardness (HB), flexural strength (FS), flexural modulus (E), water sorption (WS), and water solubility (SL) were assessed for this purpose. The pilot study of these copolymers showed that they have high antibacterial activity and good physicochemical properties. This paper revealed that QA:TEGs cannot replace BG:TEG due to their insufficient mechanical properties and poor behavior in water. However, the results can help to explain how QAUDMA-based materials work, and how their composition should be manipulated to produce the best performance. It was found that the longer the N-alkyl chain, the lower the HB, WS, and SL. The FS and E increased with the lengthening of the N-alkyl chain from eight to ten carbon atoms. Its further extension, to eighteen carbon atoms, caused a decrease in those parameters.
... THF was dried in a circulating distillation apparatus over sodium under an argon atmosphere until the added benzophenone indicator turned blue-violet and then stored over molecular sieves. 3,6-Bis(5-bromopyrid-2-yl)-2,5-dihydro-2,5bis(2-octyldodecyl)pyrrolo [3,4-c]pyrrole-1,4-dion (PyDPPPy), 36 PPyDPPPyT2, 36 and P(4VP•MeI-co-styrene) 46 were synthesized according to modified literature procedures (see Supporting Information for experimental details). The synthesis of P(g 4 2T-TT), 47 P(g 4 2T-T), 48 P(NDIOD2CN2T2), 49 P(EO-NDIT2), 50 PmmpP, 51 P3HT, 52 P(NDIOD2ThF4Th), 53 P(DPPThF4Th), 54 Pd 2 (dba) 3 , 51 and 2-octyldodec-1-yl iodide 55 is published elsewhere. ...
... Quaternary ammonium polyethyleneimine Streptococcus mutans [29] Preparation of chitosan-gpoly(acrylamide)/montmorillonite superabsorbent polymer composites: studies on swelling, thermal, and antibacterial properties Chitosan-gpoly(acrylamide)/ montmorillonite Chitosan Staphylococcus aureus; Escherichia coli [30] Polyethylene/silver-nanofiber composites: a material for antibacterial films Polyethylene Silver nanofiber Escherichia coli [31] A novel antibacterial resin composite for improved dental restoratives ...
The manufacturing of sanitary and household furniture on a large scale with inherently antimicrobial properties is an essential field of research. This work focuses on the synthesis of polymer composites based on the unsaturated polyester of resin loaded with 5 wt.%-Triclosan produced by a co-mixing approach on automated technological complex with a potential for broad applications. According to findings, the polymer composite has a non-porous structure (surface area < 1.97 m2/g) suitable for sanitary applications to reduce the growth of bacteria. The chemical composition confirmed the presence of major elements, and the inclusion of Triclosan was quantitatively confirmed by the appearance of chlorine on XRF (1.67 wt.%) and EDS (1.62 wt.%) analysis. Thermal analysis showed the difference of 5 wt.% in weight loss, which confirms the loading of Triclosan into the polymer matrix. The polymer composite completely inhibited the strains of S.aureus 6538-P, S. aureus 39, S.epidermidis 12228, and Kl. Pneumoniae 10031 after 5-min contact time. The antimicrobial effects against Kl.pneumoniae 700603, Ps.aeruginosa 9027 and Ps.aeruginosa ТА2 strains were 92.7%, 85.8% and 18.4%, respectively. The inhibition activity against C.albicans 10231 and C.albicans 2091 was 1.6% and 82.4%, respectively; while the clinical strain of C.albicans was inhibited by 92.2%. The polymer composite loaded with 5 wt.%-Triclosan displayed a stability over the period that illustrates the possibility of washing the composite surface.
... The broad spectrum against Gram-positive and Gram-negative bacteria led to the development of glass ionomer cements, sealers, adhesives, and resin composites containing QA-PEI [63]. Even at low concentrations such as 1 wt.% of QA-PEI, the materials show antibacterial activity against essential bacteria such as S. mutans immediately and after three months [64]. ...
... At a nano-sized level, quaternary ammonium polyethylenimine derivatives (QA-PEI) nanoparticles have gained interest due to their broad antimicrobial properties [63]. QA-PEI incorporated in resin composites has been demonstrated in several studies [64,82]. Other physical interaction approaches have been discussed in the literature, such as materials with zwitterion-based [83], ethylene glycol-based [84], and bacterial-release [81] surfaces. ...
Resin-based restorative dental materials such as composite resins, glass ionomer, and adhesive systems are primarily used to restore defective tooth structures. The development of pathogenic bacterial biofilm over the restorative material is one of the most significant trigger factors for secondary caries development. Dental caries lesions around restorations have been the main reason for operative treatment failure, and these lesions are related to the biofilm accumulation around these restorations. Recently, nanotechnology advances have led to incorporating nano-sized particles, particularly metals that exhibit antimicrobial properties. Diverse antimicrobial nanoparticles are promising the development of materials with antibiofilm properties. Dental materials formulated with nanoparticles presenting large surface-to-volume ratios and specific physical and chemical properties have demonstrated outstanding potential to control the formation of biofilms and could improve caries lesions inhibition. This chapter provides a broad overview of antibacterial nanoparticles applied to restorative dentistry, their synthesis, properties, and interactions with pathogenic microorganisms. Secondly, the range of dental restorative materials that demonstrate antimicrobial properties after nanoparticle incorporation is outlined, and in‐depth analysis and comparison of antimicrobial nanomaterials are provided, representing the next generation of antibacterial dental materials. Finally, this chapter looks into the potential future of these materials to researchers in other fields, dental materials science, and dental practitioners.
