Antimicrobial Polyurethane Thermosets Based on Undecylenic Acid: Synthesis and Evaluation

Abstract

In the present study, plant oil-derived surface-modifiable polyurethane thermosets are presented. Polyol synthesis is carried out taking advantage of thiol-yne photopolymerization of undecylenic acid derivatives containing methyl ester or hydroxyl moieties. The prepared methyl ester-containing polyurethanes allow surface modification treatment to enhance their hydrophilicity and impart antimicrobial activity through the following two steps: i) grafting poly(propylene glycol) monoamine (Jeffamine M-600) via aminolysis and ii) Jeffamine M-600 layer complexation with iodine. The antimicrobial activity of the iodine-containing polyurethanes is demonstrated by its capacity to inhibit the growth of Staphylococcus aureus, and Candida albicans in agar media.

Isocyanate‐Free, UV‐Crosslinked Poly(Hydroxyurethane) Networks: A Sustainable Approach toward Highly Functional Antibacterial Gels

“…With the model reactions discussed above in mind, there are two different ways to prepare a crosslinked PHU film. One route is aminolysis first followed by the thiol–ene crosslinking and the second route is the opposite, i.e., the thiol–ene addition first followed by the aminolysis crosslinking . Of the two routes, we chose the first one as the sole film preparation method due to the ambient reaction conditions (room temperature) and much shorter curing time (minutes compared to several hours), which is more practical during large‐scale application.…”

“…One route is aminolysis first followed by the thiol-ene crosslinking and the second route is the opposite, i.e., the thiol-ene addition first followed by the aminolysis crosslinking. [21] Of the two routes, we chose the first one as the sole film preparation method due to the ambient reaction conditions (room temperature) and much shorter curing time (minutes compared to several hours), which is more practical during large-scale application. Thiol-ene addition by nature is a radical reaction but has a superior oxygen resistance compared to the conventional radical reactions.…”

Click chemistry for the synthesis of biobased polymers and networks derived from vegetable oils

“…This PU was modified by a thiol-ene reaction using 7-mercapto-4-methylcoumarin (Cm-SH), DMPA (dissolved in ACN). In follow-up work, 195 intermediate reaction products to yield VSD, methyl 10-undecynoate (MUDY), and 10-undecynyl alcohol (UDYO) were reacted with 3,6-dioxa-1,8-octanedithiol and DMPA at room temperature for 1 h under UV radiation to yield different new polyols (Fig. 15-b).…”

Bio-Based Polymers with Antimicrobial Properties towards Sustainable Development

“…The synthesized polyols were used to prepare several PU formulations with enhanced surface hydrophilicity and antimicrobial properties after aminolysis with poly(propylene glycol) monoamine (Jeffamine ® M-600) and complexation with iodine. The antibacterial activity of these systems was tested against P. aeruginosa , S. aureus , and C. albicans [320], where effectiveness was only observed for Gram-positive bacteria and fungi but not for Gram-negative bacteria.…”