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Polymers 2018, 10(6), 639; https://doi.org/10.3390/polym10060639

Exploring the Long-Term Hydrolytic Behavior of Zwitterionic Polymethacrylates and Polymethacrylamides

1
Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, D-14476 Potsdam-Golm, Germany
2
Fraunhofer Institute of Applied Polymer Research IAP, Geiselberg-Str. 69, D-14476 Potsdam-Golm, Germany
3
Institute of Analytical Chemistry—Biogrenzflächen, Ruhr-Universität Bochum, Universitätsstr. 150, D-44801 Bochum, Germany
*
Author to whom correspondence should be addressed.
Received: 19 May 2018 / Revised: 4 June 2018 / Accepted: 6 June 2018 / Published: 8 June 2018
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Abstract

The hydrolytic stability of polymers to be used for coatings in aqueous environments, for example, to confer anti-fouling properties, is crucial. However, long-term exposure studies on such polymers are virtually missing. In this context, we synthesized a set of nine polymers that are typically used for low-fouling coatings, comprising the well-established poly(oligoethylene glycol methylether methacrylate), poly(3-(N-2-methacryloylethyl-N,N-dimethyl) ammoniopropanesulfonate) (“sulfobetaine methacrylate”), and poly(3-(N-3-methacryamidopropyl-N,N-dimethyl)ammoniopropanesulfonate) (“sulfobetaine methacrylamide”) as well as a series of hitherto rarely studied polysulfabetaines, which had been suggested to be particularly hydrolysis-stable. Hydrolysis resistance upon extended storage in aqueous solution is followed by 1H NMR at ambient temperature in various pH regimes. Whereas the monomers suffered slow (in PBS) to very fast hydrolysis (in 1 M NaOH), the polymers, including the polymethacrylates, proved to be highly stable. No degradation of the carboxyl ester or amide was observed after one year in PBS, 1 M HCl, or in sodium carbonate buffer of pH 10. This demonstrates their basic suitability for anti-fouling applications. Poly(sulfobetaine methacrylamide) proved even to be stable for one year in 1 M NaOH without any signs of degradation. The stability is ascribed to a steric shielding effect. The hemisulfate group in the polysulfabetaines, however, was found to be partially labile. View Full-Text
Keywords: polyzwitterions; stability; polymer degradation; hydrolysis; polysulfobetaine; polysulfabetaine; anti-fouling materials polyzwitterions; stability; polymer degradation; hydrolysis; polysulfobetaine; polysulfabetaine; anti-fouling materials
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Schönemann, E.; Laschewsky, A.; Rosenhahn, A. Exploring the Long-Term Hydrolytic Behavior of Zwitterionic Polymethacrylates and Polymethacrylamides. Polymers 2018, 10, 639.

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