Abstract
In this study, the antimicrobial agents of mono(hydroxyethoxyethyl)phthalate (M(HEEP)2) with different metal of M = Zn, Mn, Pb, and Ca were synthesized from diethylene glycol (DEG), phthalic anhydride (PA), and divalent metal acetates including calcium acetate, zinc acetate, manganese acetate, and lead acetate, respectively. The waterborne urethane oil (WUO) dispersions synthesized from linseed oil, diisocyanates (hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI)), dimethylolpropionic acid at NCO/OH molars of 0.9, by acetone processing method were described as in our previous report. The M(HEEP)2 antimicrobial agents as well as the commercial nanosilver powder were added into WUO dispersions as the antimicrobial coatings. The effects of various antimicrobial agents and dosages (0.0, 0.2, 0.6, 0.8, 1.0, 2.0, and 4.0 phr) on antimicrobial activity of WUO films against gram-negative bacterium of Escherichia coli, gram-positive bacterium of Staphylococcus aureus, brown-rot fungus of Gloeophyllum trabeum, and white-rot fungus of Lenzites betulina were assessed. In addition, the film properties of the best antimicrobial WUO coatings were also examined. The results showed that the antimicrobial agents of mono(hydroxyethoxyethyl) phthalate M(HEEP)2 (M = Zn, Mn, Pb, and Ca) powders should certainly be synthesized by FTIR, 1H-NMR, 13C-NMR, and energy-dispersive X-ray spectroscopy (EDS) identifications and the yields of them were 43–55%. The results also revealed that the WUO film synthesizing with HDI films containing Zn(HEEP)2 of 2.0 phr and Pb(HEEP)2 of 0.4 phr had the best antibacterial activity for E. coli and S. aureus, respectively. The IPDI films containing Zn(HEEP)2 of 1.0 phr had the best antibacterial activity for both E. coli and S. aureus. For antifungal activity, the WUO film synthesizing with HDI films containing Pb(HEEP)2 of 0.8 phr and Zn(HEEP)2 of 2.0 phr as well as IPDI films containing Mn(HEEP)2 of 0.2 phr and Zn(HEEP)2 of 4.0 phr had the best performances against G. trabeum and L. betulina, respectively. Comparing with commercial nanoAg powder, the Zn(HEEP)2 and Pb(HEEP)2 had a superior antifungal efficiency for G. trabeum and L. betulina, while it had a slightly inferior efficiency in the antibacterial activity for E. coli and S. aureus. On the properties of WUO films, adding metal-containing antimicrobial agents could slightly enhance the thermal stability, but lowered the gloss of all films, however, the Tg value increased for HDI film and decreased for IPDI film. In addition to this, they had no significant difference in the film properties including hardness, impact resistance, bending resistance, adhesion, mass retention, and light-fastness between the WUO films with and without adding antimicrobial agents.
Highlights
The dwindling petroleum supplies have enormously increased the material cost as well as deep environmental concerns
The results revealed that the waterborne urethane oil (WUO) film synthesizing with hexamethylene diisocyanate (HDI) films containing Zn(HEEP)2 of 2.0 phr and Pb(HEEP)2 of 0.4 phr had the best antibacterial activity for E. coli and S. aureus, respectively
The results showed that the yields of the M(HEEP)2 were increased to 43.4–55.1%
Summary
The dwindling petroleum supplies have enormously increased the material cost as well as deep environmental concerns. In order to reduce the reliance on petrochemicals, employing renewable resources, such as natural linseed oil, tung oil, or castor oil, to replace petroleum derivatives for manufacturing wood coatings [1,2,3,4,5,6] and currently, waterborne coatings have received more attention as a substitute for solvent-borne coatings due to their nontoxic and nonflammable character as well as the emission of lesser or no volatile organic compounds (VOCs) [7,8]. Reported that zinc incorporated linseed oil based polyesteramide was successfully synthesized at a lower temperature without an organic solvent. It was found that minor incorporation of zinc in linseed oil based polyesteramide exhibited improved antibacterial activities against Escherichia coli and Staphylococcus aureus. Zafar et al [12] founded that zinc and cadmium incorporated linseed oil based poly(esteramide-urethane) (Zn/Cd-LPEAUr) were performed against E. coli and S. aureus, and compared with those of petroleum-based metal containing polyurethanes. Zafar et al [13,14]
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