Synthesis of Novel Sulfobetaine Polymers with Differing Dipole Orientations in Their Side Chains, and Their Effects on the Antifouling Properties

Abstract

The impact of the orientation of zwitterionic groups, with respect to the polymer backbone, on the antifouling performance of thin hydrogel films made of polyzwitterions is explored. In an extension of the recent discussion about differences in the behavior of polymeric phosphatidylcholines and choline phosphates, a quasi‐isomeric set of three poly(sulfobetaine methacrylate)s is designed for this purpose. The design is based on the established monomer 3‐[N‐2‐(methacryloyloxy)ethyl‐N,N‐dimethyl]ammonio‐propane‐1‐sulfonate and two novel sulfobetaine methacrylates, in which the positions of the cationic and the ionic groups relative to the polymerizable group, and thus also to the polymer backbone, are altered. The effect of the varied segmental dipole orientation on their water solubility, wetting behavior by water, and fouling resistance is compared. As model systems, the adsorption of the model proteins bovine serum albumin (BSA), fibrinogen, and lysozyme onto films of the various polyzwitterion surfaces is studied, as well as the settlement of a diatom (Navicula perminuta) and barnacle cyprids (Balanus improvisus) as representatives of typical marine fouling communities. The results demonstrate the important role of the zwitterionic group's orientation on the polymer behavior and fouling resistance.

Synthetic and natural polyampholytes: Structural and behavioral similarity

“…Due to high charge density, biocompatibility, nontoxicity, protein‐ and cell‐repellent properties, antithrombogenic, and antipolyelectrolyte behavior in saline media, polyzwitterions continue to attract interest in the area of biomedical application 55,85,86 . The biological effects of polyzwitterionic hydrogel films of about 100 nm thickness have been evaluated with respect to model proteins (BSA, lysozyme, fibrinogen).…”

Polybetaines in Biomedical Applications

“…Some structures of betainic monomers and polybetaines with antifouling properties are presented in [33] P4VPPC-co-PDMAPC copolymer [33] P4VPPC-co-PDMAPC copolymer Polybetaines based on poly(acrylamides) (PAA)…”

Biomedical Uses of Sulfobetaine-Based Zwitterionic Materials

“…A more comprehensive set of structures has also been examined by altering the alkyl chain lengths and ammonium functional moieties (Figure 4d). 62 The results from studies to vary the chemical topology and features of SB motifs point to subtle and complex structureproperty relationships for antifouling performance. 63 The continued exploration of new structural variants is important to further understand and optimize the performance of SB materials for antifouling applications.…”