title: Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols.
abstract: In this study, a simple and versatile synthetic approach was developed to prepare bactericidal polyurethane coatings. For this purpose, introduction of both quaternary ammonium salts (QASs), with well-known antibacterial activity, and reactive hydroxyl groups on to the backbone of soybean oil was considered. Epoxidized soybean oil was reacted with diethylamine and the intermediate tertiary amine containing polyol was reacted with two different alkylating agents, methyl iodide and benzyl chloride, to produce MQAP and BQAP, respectively. These functional polyols were reacted with different diisocyanate monomers to prepare polyurethane coatings. Depending on the structure of monomers used for the preparation of polyurethane coatings, initial modulus, tensile strength and elongation at break of samples were in the ranges of 122-339 MPa, 4.6-12.4 MPa and 8.4-46%, respectively. Polyurethane coatings based on isophorone diisocyanate showed proper mechanical properties and adhesion strength (0.41 MPa) for coating application. Study of fibroblast cells interaction with prepared polyurethanes showed promising cells viability in the range of 78-108%. Meanwhile, MQAP based samples with higher concentration of QASs showed better adhesion strength, surface hydrophilicity and antibacterial activity (about 95% bacterial reduction). Therefore, these materials can find applications as bactericidal coating for biomedical devices and implants.
authors.affiliation: Polyurethane Department, Iran Polymer and Petrochemical Institute, P.O. Box: 14965-115, Tehran, Iran.
authors.forename: Hadi
authors.initials: H
authors.lastname: Bakhshi
authors.affiliation: Polyurethane Department, Iran Polymer and Petrochemical Institute, P.O. Box: 14965-115, Tehran, Iran. Electronic address: h.yeganeh@ippi.ac.ir.
authors.forename: Hamid
authors.initials: H
authors.lastname: Yeganeh
authors.affiliation: Polyurethane Department, Iran Polymer and Petrochemical Institute, P.O. Box: 14965-115, Tehran, Iran.
authors.forename: Shahram
authors.initials: S
authors.lastname: Mehdipour-Ataei
authors.affiliation: National Cell Bank of Iran, Pasteur Institute of Iran, P.O. Box: 13185-1667, Tehran, Iran.
authors.forename: Mohammad Ali
authors.initials: MA
authors.lastname: Shokrgozar
authors.affiliation: Polyurethane Department, Iran Polymer and Petrochemical Institute, P.O. Box: 14965-115, Tehran, Iran.
authors.forename: Abbas
authors.initials: A
authors.lastname: Yari
authors.affiliation: National Cell Bank of Iran, Pasteur Institute of Iran, P.O. Box: 13185-1667, Tehran, Iran.
authors.forename: Seyyed Nasirodin
authors.initials: SN
authors.lastname: Saeedi-Eslami
mesh_terms: D000477:Alkylating Agents / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D020099:Coated Materials, Biocompatible / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D004548:Elasticity; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006244:Hardness; D057927:Hydrophobic and Hydrophilic Interactions; D051379:Mice; D011108:Polymers / Q000737:chemistry*; D011140:Polyurethanes / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013024:Soybean Oil / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013499:Surface Properties; D013718:Tensile Strength; D014783:Viscosity
chemical_list: D000477:Alkylating Agents; D000588:Amines; D000900:Anti-Bacterial Agents; D020099:Coated Materials, Biocompatible; D011108:Polymers; D011140:Polyurethanes; D000644:Quaternary Ammonium Compounds; C554142:epoxidized soybean oil; C024617:polyol; D013024:Soybean Oil