Post-polymerization modification of poly(vinyl amine) with functional epoxides : multifunctional, antimicrobial, protein-like polymers

• Polymeranaloge Reaktion von Poly(vinyl amin) mit funktionellen Epoxiden : multifunktionelle, antimikrobielle, proteinartige Polymere

Schmalen, Angela; Möller, Martin (Thesis advisor); Pich, Andrij (Thesis advisor)

Aachen : Publikationsserver der RWTH Aachen University (2015)
Dissertation / PhD Thesis

Aachen, Techn. Hochsch., Diss., 2014

Abstract

The increasing resistance of bacteria towards common antimicrobial agents causes a significant need for new antimicrobial compounds. In this context, the present thesis deals with the preparation and characterization of novel multifunctional poly(vinyl amine)s. Poly(vinyl amine) was successfully functionalized with quaternary ammonium groups and alkyl groups with the goal to mimic natural antimicrobial peptides and give access to novel antimicrobial agents. The post polymerization modification with functional epoxides was chosen as a versatile approach to introduce hydrophobic and hydrophilic functionalities into the polymer. The degree of functionalization can easily be adjusted by the ratio of functional epoxides to amine groups giving access to a high variety of polymers. The novel multifunctional poly(vinyl amine)s were characterized in detail with regard to the influence of the hydrophilic/hydrophobic balance on several properties in aqueous solution and coated on surfaces. The influence of the hydrophilic/hydrophobic balance on the antimicrobial activity, the critical aggregation concentration, and the penetration ability into model membranes was thoroughly investigated. Different microstructures were successfully introduced into functional polymers having an identical chemical composition and molecular weight. The influence of these microstructures on the antimicrobial effect, the critical aggregation concentration, the viscosity, the ability to penetrate into a model DPPC membrane, the ability to penetrate into the outer/inner membrane of E. coli, and the hemolytic activity of the polymers was determined. The resulting multifunctional polymers can, e.g., be used as antimicrobial agents for surface coatings or textile finishings.