Synthesis and modification of poly(ethyl 2-(imidazol-1-yl)acrylate) (PEImA)

Rössel, Carsten; Billing, Mark; Görls, Helmar; Festag, Grit; Grube, Mandy; Bellstedt, Peter; Nischang, Ivo; Schacher, Felix H.

doi:10.1016/j.polymer.2017.08.058

Cited by 8 publications

(10 citation statements)

References 41 publications

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“…Although this singular case did not exhibit improved antifouling performance compared to that of established polyzwitterions, the strong effect of this structural variation on the fouling behavior is obvious and merits further investigation. This is equally true for attempts to vary the polyzwitterion architecture, e.g., of type D or E, seemingly realized only exceptionally for polycarboxybetaines. ,,, …”

Section: Conclusion and Perspectivementioning

confidence: 99%

“…Even if it might seem surprising, our expectations concerning the variation of the ionic groups within the zwitterionic moiety are low. Although the hydrophilicity of specific anionic groups in zwitterions may vary notably, ,, the sulfonate group appears to be the most useful one for the above-discussed reasons, with the important exception of the ammonio acetate motif (as in TGMA or derivatives with the ectoine or imidazolium moiety). Concerning the nature of the cationic group, the perspective is less clear but still seems limited.…”

Section: Conclusion and Perspectivementioning

confidence: 99%

“…This is equally true for attempts to vary the polyzwitterion architecture, e.g., of type D or E, seemingly realized only exceptionally for polycarboxybetaines. 95,140,153,154 ■ AUTHOR INFORMATION Corresponding Authors *E-mail: laschews@uni-potsdam.de. *E-mail: axel.rosenhahn@rub.de.…”

Section: Polymersmentioning

confidence: 99%

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Molecular Design of Zwitterionic Polymer Interfaces: Searching for the Difference

2018

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The widespread occurrence of zwitterionic compounds in nature has incited their frequent use in designing biomimetic materials. Therefore, zwitterionic polymers are a thriving field. A particular interest for this particular polymer class has currently focused on their use in establishing neutral, low-fouling surfaces. After highlighting strategies to prepare model zwitterionic surfaces as well as those that are more suitable for practical purposes relying strongly on radical polymerization methods, we present recent efforts to diversify the structure of the hitherto quite limited variety of zwitterionic monomers and of the derived polymers. We identify key structural variables, consider their influence on essential properties such as overall hydrophilicity and long-term stability, and discuss promising targets for the synthesis of new variants.

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Section: Conclusion and Perspectivementioning

confidence: 99%

Section: Conclusion and Perspectivementioning

confidence: 99%

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Molecular Design of Zwitterionic Polymer Interfaces: Searching for the Difference

2018

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“…Compared to the mostly employed anti-fouling materials based on poly(ethylene oxide), polyzwitterions excel for instance in their chemical stability, in particular against oxygen and other oxidants such as chlorine [14,15,16]. Although a large variety of zwitterionic moieties has been incorporated into polymers, the vast majority of studies have focused hitherto on three poly-zwitterion families, namely poly(phosphatidylcholine)s [10,17,18,19,20], poly(carboxybetaine)s [21,22,23,24,25,26,27,28,29], and poly(sulfobetaine)s [30,31,32,33,34,35,36,37,38,39]. While the interest in the former family is due to their similarity to phospholipids [40,41,42], the latter two families are characterized by good stability, high structural variability, and straightforward synthetic accessibility [2,3].…”

Section: Introductionmentioning

confidence: 99%

Surface Modification by Polyzwitterions of the Sulfabetaine-Type, and Their Resistance to Biofouling

et al. 2019

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Films of zwitterionic polymers are increasingly explored for conferring fouling resistance to materials. Yet, the structural diversity of polyzwitterions is rather limited so far, and clear structure-property relationships are missing. Therefore, we synthesized a series of new polyzwitterions combining ammonium and sulfate groups in their betaine moieties, so-called poly(sulfabetaine)s. Their chemical structures were varied systematically, the monomers carrying methacrylate, methacrylamide, or styrene moieties as polymerizable groups. High molar mass homopolymers were obtained by free radical polymerization. Although their solubilities in most solvents were very low, brine and lower fluorinated alcohols were effective solvents in most cases. A set of sulfabetaine copolymers containing about 1 mol % (based on the repeat units) of reactive benzophenone methacrylate was prepared, spin-coated onto solid substrates, and photo-cured. The resistance of these films against the nonspecific adsorption by two model proteins (bovine serum albumin—BSA, fibrinogen) was explored, and directly compared with a set of references. The various polyzwitterions reduced protein adsorption strongly compared to films of poly(n‑butyl methacrylate) that were used as a negative control. The poly(sulfabetaine)s showed generally even somewhat higher anti-fouling activity than their poly(sulfobetaine) analogues, though detailed efficacies depended on the individual polymer–protein pairs. Best samples approach the excellent performance of a poly(oligo(ethylene oxide) methacrylate) reference.

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“…Synthesis of poly(2-(imidazole-1-yl)acrylic acid) (PImAA), (Scheme ): The synthesis of ethyl 2-(imidazole-1-yl)acrylate (EImA) and anionic polymerization in tetrahydrofuran (THF) with potassium tert -butoxide (KO t Bu) as an initiator, as well as the polymer modifications, were performed as described in the literature . The polymers were characterized by proton nuclear magnetic resonance ( 1 H NMR) (300 MHz, D 2 O) and size exclusion chromatography (SEC, 0.1 M NaCl/0.3% TFA in water, P2VP calibration).…”

Section: Materials and Methodsmentioning

confidence: 99%

Thermal Transport in Ampholytic Polymers: The Role of Hydrogen Bonding and Water Uptake

et al. 2020

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The low thermal conductivity of amorphous polymers typically prevents their usage in thermal management applications. Therefore, increasing their intrinsic thermal conductivity poses an exciting scientific challenge. One approach is to promote attractive interchain interactions. Here, we investigate the thermal conductivity of several ampholytic polymers. This unique class of polymers offers H-bond donor and acceptor groups in each repeat unit and constitutes an onecomponent system. We use IR spectroscopy to characterize the bonding strength and motifs based on the carbonyl peak. For the dry ampholytic polymers, we find a correlation between H-bond strength and thermal conductivity. We also characterized the influence of hydration at various relative humidity conditions, which mostly led to an increase in thermal conductivity. This increase can be rationalized by the formation of a water-polymer nanocomposite material and can be described by volume-weighted mixing models. conductivity. This is an ongoing challenge to be addressed by polymer chemists and engineers over the next years. ASSOCIATED CONTENT Supporting Informationthermal conductivity measurements, IR spectroscopy of individual polymers, DSC measurements, effective medium mixing models, and microscopy of the transducer layer

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Synthesis and modification of poly(ethyl 2-(imidazol-1-yl)acrylate) (PEImA)

Cited by 8 publications

References 41 publications

Molecular Design of Zwitterionic Polymer Interfaces: Searching for the Difference

Molecular Design of Zwitterionic Polymer Interfaces: Searching for the Difference

Surface Modification by Polyzwitterions of the Sulfabetaine-Type, and Their Resistance to Biofouling

Thermal Transport in Ampholytic Polymers: The Role of Hydrogen Bonding and Water Uptake

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