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Unraveling the spontaneous zwitterionic copolymerization mechanism of cyclic imino ethers and acrylic acid
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Steinkoenig, Jan, de Jongh, Patrick A. J. M., Haddleton, David M., Goldmann, Anja S., Barner-Kowollik, Christopher and Kempe, Kristian (2018) Unraveling the spontaneous zwitterionic copolymerization mechanism of cyclic imino ethers and acrylic acid. Macromolecules, 51 (2). pp. 318-327. doi:10.1021/acs.macromol.7b02608 ISSN 0024-9297 .
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Official URL: http://doi.org/10.1021/acs.macromol.7b02608
Abstract
We report a high-resolution electrospray ionization mass spectrometric (HR ESI MS) access route leading to in-depths insight into the spontaneous zwitterionic copolymerization mechanism between cyclic imino ethers (i.e. 2-methyl-2-oxazoline (MeOx), 2-ethyl-2-oxazoline (EtOx) or 2-ethyl-2-oxazine (EtOz)) with acrylic acid (AA), exploiting the characteristic species accumulating during the copolymerization as well as tandem mass spectrometry (MS/MS). We demonstrate preferences in α,ω-end group formation by screening various feed ratios of cyclic imino ethers and acrylic acid (e.g. MeOx:AA = 1:1; MeOx:AA = 2:1; MeOx:AA = 1:2). Critically, a calibration curve – based on AA-MeOx-AA dimer – was established allowing for semi-quantitative determination of the end group ratios with different feed ratios of acrylic acid. The formation of, previously suggested, alternating copolymers was confirmed by MS/MS experiments. Deviations from an ideal alternating composition were found to decrease from MeOx to EtOx to EtOz. The results of (semi-quantitative) HR ESI MS and MS/MS measurements suggest, for the first time presented in such precision, a polymerization mechanism for the spontaneous zwitterionic (alternating) copolymerization indicating optimal monomer ratios and pairings.
| Item Type: | Journal Article | |||||||||||||||||||||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry | |||||||||||||||||||||||||||||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||||||||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Polyzwitterions, Copolymers, Acrylic acid, Imino compounds | |||||||||||||||||||||||||||||||||||||||
| Journal or Publication Title: | Macromolecules | |||||||||||||||||||||||||||||||||||||||
| Publisher: | American Chemical Society | |||||||||||||||||||||||||||||||||||||||
| ISSN: | 0024-9297 | |||||||||||||||||||||||||||||||||||||||
| Official Date: | 23 January 2018 | |||||||||||||||||||||||||||||||||||||||
| Dates: |
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| Volume: | 51 | |||||||||||||||||||||||||||||||||||||||
| Number: | 2 | |||||||||||||||||||||||||||||||||||||||
| Page Range: | pp. 318-327 | |||||||||||||||||||||||||||||||||||||||
| DOI: | 10.1021/acs.macromol.7b02608 | |||||||||||||||||||||||||||||||||||||||
| Status: | Peer Reviewed | |||||||||||||||||||||||||||||||||||||||
| Publication Status: | Published | |||||||||||||||||||||||||||||||||||||||
| Access rights to Published version: | Restricted or Subscription Access | |||||||||||||||||||||||||||||||||||||||
| Date of first compliant deposit: | 22 December 2017 | |||||||||||||||||||||||||||||||||||||||
| Date of first compliant Open Access: | 8 January 2019 | |||||||||||||||||||||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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