Development of a New Monomer for the Synthesis of Intrinsic Antimicrobial Polymers with Enhanced Material Properties

Abstract

The use of biocidal compounds in polymers is steadily increasing because it is one solution to the need for safety and hygiene. It is possible to incorporate an antimicrobial moiety to a polymer. These polymers are referred to as intrinsic antimicrobial. The biocidal action results from contact of the polymer to the microorganisms, with no release of active molecules. This is particularly important in critical fields like food technology, medicine and ventilation technology, where migration or leaching is crucial and undesirable. The isomers N-(1,1-dimethylethyl)-4-ethenyl-benzenamine and N-(1,1-dimethyl-ethyl)-3-ethenyl-benzenamine (TBAMS) are novel (Co-)Monomers for intrinsic anti-microbial polymers. The secondary amines were prepared and polymerized to the corresponding water insoluble polymer. The antimicrobial activity was analyzed by the test method JIS Z 2801:2000. Investigations revealed a high antimicrobial activity against Staphylococcus aureus and Escherichia coli with a reduction level of >4.5 log10 units. Furthermore, scanning electron microscopy (SEM) of E. coli. in contact with the polymer indicates a bactericidal action which is caused by disruption of the bacteria cell membranes, leading to lysis of the cells.

Potential of the polymer poly-[2-(tert-butylamino) methylstyrene] as antimicrobial packaging material for meat products

“…Therefore, poly(TBAMS) was synthesized according to Brodkorb et al . (). Petri dishes coated with a thin film of poly(TBAMS) were prepared in the following manner.…”

“…This SAM ® polymer was developed in 2001 by Creavis Technologies & Innovation of Degussa (Brodkorb et al . ). According to Thölmann et al .…”

“…The first industrial prototype of SAM â polymers was poly-[2-(tert-butylamino)ethyl methacrylate] (poly(TBAEMA)). This SAM â polymer was developed in 2001 by Creavis Technologies & Innovation of Degussa (Brodkorb et al 2015). According to Th€ olmann et al (2003), the antimicrobial activity of these polymers is based on the three-dimensional helical structure with a high concentration of protonated functional amino groups.…”

“…A low T G leads to a sticky surface. Based on this polymer, a new SAM â polymer, poly-[2-(tert-butylamino) methylstyrene] (poly(TBAMS)), with a raised T G was developed (Brodkorb et al 2015). Figure 1 shows the chemical structure of poly(TBAEMA) and the new polymer poly (TBAMS).…”

“…The new polymer poly(TBAMS) has a glass transition temperature (T G ) of 68°C. Furthermore, a high antimicrobial activity was detected against Staphylococcus aureus and Escherichia coli at 35°C after 2 h of contact time (Brodkorb et al 2015). For the implementation as antimicrobial packaging material, however, typical conditions of meat supply chains have to be considered.…”