Novel refreshable N‐halamine polymeric biocides containing imidazolidin‐4‐one derivatives

Abstract

A novel cyclic‐amine monomer, 1‐acryloyl‐2,2,5,5‐tetramethylimidazolidin‐4‐one (ACTMIO), was synthesized in a good yield through the reaction of acryloyl chloride with 2,2,5,5‐tetramethylimidazolidin‐4‐one and was fully characterized with Fourier transform infrared and 1H NMR studies. ACTMIO was copolymerized with several widely used acrylic and vinyl monomers under ordinary conditions. In the presence of triallyl‐1,3,5‐triazine‐2,4,6(1H,3H,5H)‐trione, ACTMIO was easily grafted onto most textile fabrics. After regular chlorine bleach treatment, N‐halamine derivatives of the corresponding polymeric materials exhibited antibacterial properties against Escherichia coli, and these properties were durable and refreshable with chlorine bleaching. The relationship between the structures and antibacterial properties of the samples is further discussed. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3073–3084, 2001

Acyclic N-Halamine Coated Kevlar Fabric Materials: Preparation and Biocidal Functions

“…N-Halamines are compounds containing one or more nitrogen-halogen covalent bonds that are normally formed by the chlorination or bromination of imide, amide, or amine groups. [6][7][8] The biocidal actions of N-halamines are attributed to the oxidative properties of the N-Cl or N-Br bonds; that is, upon contact with microorganisms, an oxidative reaction occurs, leading to the inactivation of bioagents. This process consumes halogens, but the consumed halogens can be easily recharged by another chlorination or bromination treatment.…”

“…Thanks to these attractive properties, monomeric and polymeric N-halamines have found broad applications as disinfectants in the field of water treatments, coatings, textiles, and so forth. [6][7][8][9][10][11][12][13] To introduce N-halamine functionality into fire/thermal protective fabrics to achieve multipurpose protections, polymethacrylamide (PMAA) was coated onto Kevlar fabrics using a simple dip-pad-cure approach. After exposure to chlorine bleach, part of the amide groups of the coated PMAA chains were transformed into N-halamines, 14 providing potent, durable, and rechargeable antibacterial, antifungal, antiviral, and antispore functions without compromising the original thermal and mechanical properties of Kevlar fabrics.…”

Recent Developments in Finishing of Synthetic Fibers for Medical Applications

“…The grafting process is the same for that used for polyester (as reported before) [53][54][55]. Highperformance fibers, such as Nomex and Kevlar, have found large markets and many demanding end-uses because of their superior mechanical properties, fire resistance, and excellent thermal, chemical and oxidative stabilities.…”

“…After regular chlorine bleach treatment, some of the N -3 amide groups of the imidazolidin-4-one structures in the co-polymers and the grafted fabrics could be transformed into stable N -halamine groups, which provided powerful durable and refreshable antibacterial efficacies against E. coli. The antimicrobial efficacies and stabilities of the polymeric N -halamines could be rationalized by the hydrophilic/hydrophobic property of the substrates and mobility/swellability of the polymeric molecules as well as the surface area of the materials and migration of active chlorine [54].…”

“…-5,5-dimethyl) Hydantoin. Grafting of PP with this monomer in order to produce antimicrobial fabric was done with the same procedure as explained before in case of PET grafting [53][54][55].…”