Antibacterial poly(ethylene terephthalate) surfaces obtained from thymyl methacrylate polymerization

Abstract

Thymol, an antibacterial agent was used for the preparation of a methacrylic monomer. The conventional and atom transfer radical (ATRP) polymerizations of this monomer were studied using different conditions. Then, the functionalization of poly(ethylene terephthalate) (PET) films by “grafting from” ATRP using this monomer was investigated. In this aim, a three steps procedure was developed. The surfaces were first treated by NH3 plasma treatment to incorporate primary amino functions. Then, in a second step, ATRP initiator was grafted by reaction with bromoisobutyryl bromide. Surface initiated ATRP of thymyl methacrylate was performed in solution in the presence of a sacrificial initiator. The efficiency of these reactions was confirmed by X‐ray photoelectron spectroscopy. Wetting properties and surface energy were found to vary systematically depending to the type of functionalization and grafting. The poly(thymyl methacrylate)‐grafted PET surfaces exhibit resistance to bacterial adhesion toward Pseudomonas aeruginosa, Listeria monocytogenes, and Staphylococcus aureus strains. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1975–1985

Control of surface radical graft polymerization on polyester fibers by using Hansen solubility parameters as a measurement of the affinity of chemicals to materials

“…Radical gra polymerization has been considered as a possible and effective method for surface modication of inert polymers where various functional vinyl monomers can be incorporated. [10][11][12][13][14][15] The most common initiation process is thermal decomposition of initiators through homolytic cleavage of weak covalent bonds in the molecule to free radicals. These initiators mainly fall into peroxy molecules due to the structural features and tendency in abstracting active hydrogens on polymers.…”

Exploring the potential of polyethylene terephthalate in the design of antibacterial surfaces

“…The effectiveness against S. aureus and E. coli increased with the increased grafting percentage. Bedel et al [30] performed ATRP polymerization of thymol monomer. The results showed that the water contact angle increased from 81° to 99° for samples treated with thymyl methacrylate.…”

Hydrophilic PET surfaces by aminolysis and glycopolymer brushes chemistry

“…The contact angle was measured within 10 s of placing the drop (3 μL) on the surfaces and an average of six measurements was reported. The approach of Good, Van Oss, and Chaudhury (acid–base theory) was used to calculate the surface free energy as previously reported . The surface energy parameters of the acid–base component of the probe liquids were previously described …”

“…However, the low hydrophilicity of PET had limited its applications. There are many researches studying on the modification of polymers such as plasma treatment, UV irradiation, “grafting onto” and “grafting from” treatments, and so on . Grafting of hydrophilic monomers containing hydroxyl groups onto PET is one of the effective ways to increase its hydrophilicity.…”

“…In our previous work, we have published different methods to modify PET surfaces as films and fibers . Among them, we have studied a two‐step procedure allowing the grafting of carbohydrates on PET surfaces: (1) primary amino groups were generated on PET surfaces by aminolysis reaction with diamines (2) grafting of mono‐ and disaccharides by reductive amination .…”