Synthesis and evaluation of antibacterial polyurethane coatings made from soybean oil functionalized with dimethylphenylammonium iodide and hydroxyl groups

• Published in: Journal of biomedical materials research. Part A 2013-06, Vol.101A (6), p.1599-1611
• Main Authors: Bakhshi, Hadi, Yeganeh, Hamid, Mehdipour-Ataei, Shahram
• Format: Article
• Language: English
• Subjects: Adhesion; Adhesiveness - drug effects; Aniline Compounds - chemistry; Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; antibacterial; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Bacteria; biocompatibility; Biological and medical sciences; Cell Survival - drug effects; Coated Materials, Biocompatible - chemical synthesis; Coated Materials, Biocompatible - pharmacology; coating; Coatings; Elasticity - drug effects; Escherichia coli; Escherichia coli - drug effects; Fibroblasts - cytology; Fibroblasts - drug effects; Hardness - drug effects; Hydrophobic and Hydrophilic Interactions - drug effects; Hydroxylation; Iodides; Iodides - chemistry; Magnetic Resonance Spectroscopy; Materials Testing; Medical sciences; Mice; Microbial Sensitivity Tests; Pharmacology. Drug treatments; Polymers - chemical synthesis; Polymers - chemistry; Polyols; Polyurethane resins; polyurethanes; Polyurethanes - chemical synthesis; Polyurethanes - pharmacology; Raw materials; Soya bean oil; soybean oil; Soybean Oil - chemistry; Spectroscopy, Fourier Transform Infrared; Staphylococcus aureus; Staphylococcus aureus - drug effects; Stress-strain relationships; Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases; Technology. Biomaterials. Equipments; Tensile Strength - drug effects; Viscosity - drug effects
• ISSN: 1549-3296; 1552-4965
• DOI: 10.1002/jbm.a.34461

Preparation of antibacterial polyurethane coatings from novel functional soybean oil was considered in this work. First, epoxidized soybean oil (ESBO) as a low price and widely available renewable resource raw material was subjected to the reaction with aniline using an ionic liquid as a green catalyst. The intermediate phenylamine containing polyol (SAP) was then methylated by reaction with methyl iodide to produce a polyol (QAP) with pendant dimethylphenylammonium iodide groups. To regulate the physical and mechanical properties as well as biological characteristics of final coatings, QAP was mixed with different portions of a similar soybean oil‐based polyol (MSP) without quaternary ammonium groups. The mixtures were reacted with isophorone diisocyanate to produce crosslinked polyurethane coatings. Evaluation of viscoelastic properties by DMA method revealed single phase structure with Tg in the range of 50–82°C. Stress–strain analysis of the prepared polyurethanes showed initial modulus, tensile strength, and elongation at break in the ranges of 13–299 MPa, 4.5–13.8 MPa, and 16–109%, respectively. Additionally, the coatings showed good adherence to aluminum and PVC substrates. The solvent extracted samples showed excellent biocompatibility as determined by monitoring L929 fibroblast cells morphology and MTT assay. Meanwhile, very promising antibacterial properties against both Gram‐positive (S. aureus) and Gram‐negative (E. coli) bacteria with bacterial reduction in the range of 83–100% was observed. © 2012 Wiley Periodicals, Inc. J Biomed Mater Res Part A, 2013.