Access to thermally robust and abrasion resistant antimicrobial plastics: synthesis of UV-curable phosphonium small molecule coatings and extrudable additives

Bedard, Joseph; Caschera, Alexander; Foucher, Daniel A.

doi:10.1039/d1ra00555c

Cited by 8 publications

(7 citation statements)

References 50 publications

(77 reference statements)

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“…Despite what Shum et al reported about shorter chain substituents demonstrating greater antimicrobial efficacy, the results from Figure 32 and Figure 33 showed the opposite effect, which is what is more commonly observed in the literature. 54,55 In addition, while our longer chain systems did not exhibit complete killing, the shorter chain systems of Shum et al did. 55 This can be attributed to the balance between the anchor and tail of the antimicrobial compound of interest.…”

Section: Biological Testing Of Treated Surfacescontrasting

confidence: 50%

“…Other common-touch plastics such as PS or PP have previously been looked at in the Foucher group, and it was shown that antimicrobial activity was independent of substrate type. 39,51,54,55 Approximately 0.5 mL of the polymer coating was spin coated onto the HDPE plastic substrates to deposit the coating and UV cured for 1 min to graft it to the surface. After rinsing off the unbound polymer and benzophenone, a second coating was applied to obtain a 1 mL polymer coating deposited on the HDPE substrate.…”

Section: Preparation Of Quaternary Polymer Coatingsmentioning

confidence: 99%

“…The biological testing of these coated surfaces was done using the LDI protocol, a method used for an accurate representation of bacterial growth on surfaces at the solidair interface with natural desiccation processes that bacteria on biofilms are subjected to. 46,54,55 The gram-positive Glutamicibacter soli (IAI-3) and gram-negative E. coli (ATCC 11229) were selected as our bacterial strains of interest for these studies. 46 Biological testing was performed on the non-plasma treated coating with homopolymer 5, which had the highest surface charge value, as well as the plasma treated coatings with homopolymer 4 and random copolymer 7 against G. soli and E. coli after a 24 h drying period, with the results shown in Figure 32 and Figure 33.…”

Section: Biological Testing Of Treated Surfacesmentioning

confidence: 99%

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The Preparation of New Polystyrenic Onium and Substituted Poly(Thionylphosphazene) Antimicrobials

Carafa

2024

Preprint

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<p>With increasing concern over AMR in bacteria, the synthesis of traditional and non-traditional antimicrobial polymers is of interest. The first project focuses on preparing new polystyrenic quaternary compounds that will be grafted to plastic surfaces. Three quaternary styrenic polymers (4-6) and their respective random copolymers with styrene (7-9) were synthesized and grafted onto HDPE, where biological testing of coatings 4, 5 and 7 using the LDI protocol showed some bacterial reduction with alkyl chain lengths ≥ 4. The second project focuses on synthesizing novel thionylphosphazene monomers and looking into greener polymerization routes. Two novel thionylphosphazene monomers (13-14) were synthesized and a greener polymerization route was obtained using Lewis acid-catalyzed microwave irradiation. The third project involves undertaking DFT calculations of various cyclic thionylphosphazenes to study alternate polymerization routes of these compounds. Energy calculations showed the potential for substituted thionylphosphazenes with small substituents to polymerize under ambient temperatures with Lewis acid catalysts.</p>

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Section: Biological Testing Of Treated Surfacescontrasting

confidence: 50%

Section: Preparation Of Quaternary Polymer Coatingsmentioning

confidence: 99%

Section: Biological Testing Of Treated Surfacesmentioning

confidence: 99%

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The Preparation of New Polystyrenic Onium and Substituted Poly(Thionylphosphazene) Antimicrobials

Carafa

2024

Preprint

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“…Benzaldehyde (Acros Organics) was distilled with a dephlegmator under reduced pressure prior to use. Diphenylphosphine, , [M(COD)Cl 2 ] (M = Pd, Pt), and 2-(benzo[ d ]thiazol-2-yl)aniline (NH 2 –Pbt) were prepared as reported previously. IR spectra were recorded in KBr pellets by means of an FT-801 Fourier spectrometer (Simex).…”

Section: Experimental Sectionmentioning

confidence: 99%

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Afonin,

Martynenko,

Kolybalov

et al. 2023

Inorg. Chem.

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There is unceasing interest toward transformations of phosphine derivatives, which are facilitated by transition metals. We report a facile Pd(II)-and Pt(II)-assisted P−C bond cleavage in a luminescent 2-phenylbenzothiazole-based αmethylaminophosphine (PCN, 1). Specifically, reactions between 1 and [M(COD)Cl 2 ] (M = Pd, Pt; COD = cycloocta-1,5-diene) in different solvents (methylene chloride, acetonitrile, pyridine, toluene) resulted in the formation of PPh 2 − , captured either as a bridging ligand in binuclear complexes with a {M 2 (PPh 2 ) 2 } moiety or as an adduct to COD in [Pt 2 (PPh 2 COD) 2 Cl 2 ]. The heterocyclic part transforms to annulated c-CN + species with a 1,2-dihydroquinazoline cycle formed. In the presence of pyridine as a base, annulated form c-CN + destabilizes and undergoes reverse cyclization transforming to deprotonated CN form. Quantum-chemical density functional theory (DFT) calculations predict that a crucial step in the reactions involves proton transfer from the N atom of the amino group of PCN to a neighboring molecule. A combination of high photophysical sensitivity of c-CN + toward its immediate environment and rich structural capabilities in assembling (c-CN) 2 2+ pairs in different crystal packings in a family of phases with the general formula (c-CN) 2 [M 2 (PPh 2 ) 2 Cl 4 ] allows one to fine-tune the luminescence properties of the latter. The results were rationalized as a variation of π−π intercationic spacings, which tunes the degree of excitedstate charge transfer between c-CN + cations. As a result, compounds with relatively short interplanar π−π-separation between the cations show a stronger charge-transfer-mediated bathochromic shift.

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“…It should be mentioned that phosphonium compounds have also been applied as bactericides that are covalently bonded to plastic surfaces or used as co-extrusive additives for plastic materials in goods production [ 34 ]. Such surfaces are confirmed to demonstrate antibacterial properties.…”

Section: Introductionmentioning

confidence: 99%

Sterically Hindered Quaternary Phosphonium Salts (QPSs): Antimicrobial Activity and Hemolytic and Cytotoxic Properties

Ermolaev

Arkhipova

Miluykov

et al. 2021

IJMS

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Structure–activity relationships are important for the design of biocides and sanitizers. During the spread of resistant strains of pathogenic microbes, insights into the correlation between structure and activity become especially significant. The most commonly used biocides are nitrogen-containing compounds; the phosphorus-containing ones have been studied to a lesser extent. In the present study, a broad range of sterically hindered quaternary phosphonium salts (QPSs) based on tri-tert-butylphosphine was tested for their activity against Gram-positive (Staphylococcus aureus, Bacillus сereus, Enterococcus faecalis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and fungi (Candida albicans, Trichophyton mentagrophytes var. gypseum). The cation structure was confirmed to determine their biological activity. A number of QPSs not only exhibit high activity against both Gram-positive and -negative bacteria but also possess antifungal properties. Additionally, the hemolytic and cytotoxic properties of QPSs were determined using blood and a normal liver cell line, respectively. The results show that tri-tert-butyl(n-dodecyl)phosphonium and tri-tert-butyl(n-tridecyl)phosphonium bromides exhibit both low cytotoxicity against normal human cells and high antimicrobial activity against bacteria, including methicillin-resistant strains S. aureus (MRSA). The mechanism of QPS action on microbes is discussed. Due to their high selectivity for pathogens, sterically hindered QPSs could serve as effective tunable biocides.

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Access to thermally robust and abrasion resistant antimicrobial plastics: synthesis of UV-curable phosphonium small molecule coatings and extrudable additives

Abstract: Thermally robust UV-curable phosphoniums can be utilized as chemically bound surface coatings or as additives in extruded plastics to create an antimicrobial shield on high contact surfaces.

Cited by 8 publications

References 50 publications

The Preparation of New Polystyrenic Onium and Substituted Poly(Thionylphosphazene) Antimicrobials

The Preparation of New Polystyrenic Onium and Substituted Poly(Thionylphosphazene) Antimicrobials

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Sterically Hindered Quaternary Phosphonium Salts (QPSs): Antimicrobial Activity and Hemolytic and Cytotoxic Properties

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