One‐pot synthesis of cobalt‐incorporated polyglycerol ester as an antimicrobial agent for polyurethane coatings

Abstract

Cobalt-incorporated poly(glycerol ester) (Co-PGE) was synthesized by the polycondensation of glycerol and adipic acid followed by the reaction with cobalt(II) hydroxide under solvent-free and noncatalyzed one-pot synthesis conditions. The reaction was monitored through the acid value and hydroxyl value determination. The chemical structure and molecular weight of the poly (glycerol ester) (PGE) and Co-PGE were characterized by Fourier transform infrared spectroscopy, 13 C-NMR, gel permeation chromatography, and inductively coupled plasma mass spectrometry. Co-PGE with a 59.3% degree of branching was incorporated with up to 5.0% w/w cobalt, and it exhibited antimicrobial inhibition against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans in a broth microdilution study. Polyurethane (PU) coatings were prepared by the blending of 0.5-35% w/w Co-PGE containing with 5% w/w of cobalt with blank PGE, poly(ethylene glycol) with a molecular weight of 6000, poly(caprolactone diol) with a molecular weight of 2000, and additives to react with isophorone diisocyanate. The prepared PUs demonstrated mild to high antimicrobial activities against E. coli, S. aureus, Bacillus subtilis, and C. albicans strains in a disc diffusion test. PU prepared with 0.5% w/w Co-PGE showed a mild inhibition activity against S. aureus, and PU prepared with 10% w/w Co-PGE demonstrated a high inhibition activity against C. albicans. This study demonstrated that value-added Co-PGE synthesized from glycerol has the potential as an antimicrobial agent for polymer coatings in biomedical devices. V C 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46045.

Biobased polyurethanes for biomedical applications

“…With this approach, not only PUs access intrinsic antibacterial, anti-inflammatory [ 77 ] and/or antiplatelet adhesion properties [ 78 ], but in the case of implants, the bioactive compound can also be released during PU biodegradation, allowing a stable compound release over time [ 79 ]. In order to increase PU antimicrobial activity, known bactericide with initial active hydrogen functionalities might be used, such as chloramphenicol [ 80 ] or metal derivatives such as cobalt (II) hydroxide Co(OH)2 [ 81 ]. Quaternary ammonium salts (QAS) are also proven to be bacterial adhesive inhibitors.…”

Recycling Polymeric Materials for Corrosion Control

“…High-molecular weight PEG is synthesized by suspension polymerization of waste materials [32]. It is necessary to hold the growing polymer chain in solution in the course of the poly-condensation process.…”

Thermoplastic polyurethanes for biomedical application: A synthetic, mechanical, antibacterial, and cytotoxic study

“…The most commonly used agents to exert antimicrobial effects are the quaternary onium salts, N ‐halamine, chitosan, peptides, antibiotics, nitric oxide, and metal ions 26 . As far as developing antibacterial TPUs is concerned, various active moieties have already been incorporated along with a segmented PU such as chloramphenicol, 27 cobalt, 28 or silver nanoparticles, 29 preventing thus adhesion/biofilm formation and spreading of bacteria 30–34 . Cationic agents are among the most frequently used antibacterial moieties when in contact with active surfaces, together with a potentially limited level of resistance development 35 .…”