Polyurethane Coatings Derived from 1,2,3-Triazole-Functionalized Soybean Oil-Based Polyols: Studying their Physical, Mechanical, Thermal, and Biological Properties

Abstract

Preparation of polyurethanes derived from novel 1,2,3triazole-functionalized soybean oil-based polyols and assessment of their possible biocidal activities were considered. Epoxidized soybean oil was reacted with sodium azide to produce an azide-containing polyol. The product was subjected to the cycloaddition reaction with various alkynes. Alkylation of tertiary amine-containing polyol with methyl iodide was also performed to prepare a quaternary ammonium salt (QAS)-containing polyol. The polyols and their mixtures with PEG1000 were reacted with isophorone diisocyanate to prepare polyurethane coatings. The influence of embedded functional groups on physical, mechanical, thermal and biological properties of polyurethanes was studied. Incorporation of 1,2,3-triazole groups within the polyol backbone resulted in higher storage modulus at glassy state, glass transition temperature, thermal stability and hardness of corresponding polyurethanes, while it led to lower adhesion strength and hydrophilicity. Although QAS-containing polyurethanes displayed better physical and mechanical properties, but their thermal stability were reduced. Studying the interaction of fibroblast cells with polyurethanes derived merely from oil-based polyols revealed their good cells viability (60− 110%). Moderate to high biocidal activity was detected for polyols and polyurethanes containing tertiary amine and QAS groups. Improving the hydrophilicity of polyurethanes via incorporation of PEG1000 improved their biocidal activity, while it reduced their cytocompatibility.

Biodegradable polymers from monomers based on vegetable oils

“…The carbon-carbon double bonds in glycerides are converted to epoxide groups by reaction with a peroxy acid. ESBO is nowadays commercially available [45].…”

“…Lu et al reported a further modification based on AESO to introduce carboxylic acid groups by the reaction of residual epoxy groups or hydroxyl groups with maleic anhydride (c) [44]. Recently, azide-containing polyols from soybean oil (Az-SBO) have been prepared from ESBO reacted with sodium azide (d) [45,47]. The Az-SBO products can be further subjected to the cycloaddition with different alkynes through click chemistry (e).…”

“…The Az-SBO products can be further subjected to the cycloaddition with different alkynes through click chemistry (e). These polyols were used to produce polymeric coatings with biocidal activity [45]. Other functional groups such as alcohols, double bonds in side chains, carboxylic acid or halogen groups have been introduced into vegetable oil structures though the ring opening reaction with alcohols (e.g.…”

Styrenated urethane oil synthesis via CuAAC “click” chemistry approach

“…During the CuAAC reaction, formed 1,2,3-triazole ring is chemically very stable and high conversion of functional groups can be achieved [15,[20][21][22][23]. Additionally, 1,2,3-triazole ring could establish hydrogen bonding with NH part of the urethane linkage and be in a dipole-dipole interaction with other 1,2,3-triazole ring because of 1,2,3-triazole's high polarity nature in the molecule [21][22][23]. It was mentioned that highly stable aromatic structure of 1,2,3-triazole part has an advantage of being resistant to acidic, basic and oxidative mediums [21][22][23].…”

“…Additionally, 1,2,3-triazole ring could establish hydrogen bonding with NH part of the urethane linkage and be in a dipole-dipole interaction with other 1,2,3-triazole ring because of 1,2,3-triazole's high polarity nature in the molecule [21][22][23]. It was mentioned that highly stable aromatic structure of 1,2,3-triazole part has an advantage of being resistant to acidic, basic and oxidative mediums [21][22][23]. Numerous applications of CuAAC introduce new routes in product design that have been recently studied for functionalization of polymers [22][23][24][25][26][27][28][29][30][31][32].…”