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Poly(bromoundecyl acrylate) gels

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Abstract

Initial attempts to perform nearly bulk polymerization of bromoundecyl acrylate unexpectedly produced cross-linked gels, GelCH2Cl2 and GelDMF, exhibiting some interesting chemical features. Monomer concentrations were 50% by weight using methylene chloride (CH2Cl2) and dimethylformamide (DMF) as solvents. Thermal initiation was done with AIBN (azobis[isobutyronitrile]), and analysis of GelCH2Cl2 and GelDMF suggests the isobutyronitrile radical participates in both hydrogen and bromine atomic abstraction reactions. A higher cross-linking density was obtained in DMF, 2 mmol cm−3, than in CH2Cl2, 0.6 mmol cm−3, by measuring swelling in toluene and xylene. Differential scanning calorimetry analysis of these gels reveal melting and freezing transitions over − 30 to − 50 °C, similar to non-cross-linked poly(bromoundecyl acrylate), a room-temperature liquid. Thermally driven apparent evolution of bromine from GelDMF was quantified as corresponding to about 27% of the molar-available bromine by using Ag+ potentiometry. These gel materials represent a new class of telechelic gels that can easily be reacted with diverse reagents to make them interfacially compatible with other phases.

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Data availability

Most data are available in Ms. Li’s MS thesis (see URL provided as caption to manuscript title to download thesis); other data are available on request from the corresponding author.

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Funding

This work was supported by the School of Engineering and by the Department of Chemistry, Eastern Michigan University.

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  1. Shuxiao Li

    Present address: Department of Chemistry, Wayne State University, Detroit, MI, 48202, USA

Authors and Affiliations

  1. Coating Research Institute, School of Engineering, Eastern Michigan University, Ypsilanti, MI, 48197, USA

    Shuxiao Li & John Texter

  2. Department of Chemistry, Eastern Michigan University, Ypsilanti, MI, 48197, USA

    Harriet Lindsay

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  1. Shuxiao Li
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Contributions

SL executed the experimental work (except NMR). HL contributed NMR measurements and organic reaction mechanism depictions and discussion. JT conceived of this project and supervised Ms. Li. All authors contributed to writing the manuscript.

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Correspondence to John Texter.

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Li, S., Lindsay, H. & Texter, J. Poly(bromoundecyl acrylate) gels. Polym. Bull. 79, 5825–5842 (2022). https://doi.org/10.1007/s00289-021-03768-w

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