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Efficient cationic ring-opening polymerization of diverse cyclic imino ethers: unexpected copolymerization behavior

(2011) MACROMOLECULES. 44(11). p.4320-4325
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Abstract
The recently developed fast microwave-assisted cationic ring-opening polymerization procedure for 2-oxazolines seems to be ideally suited for slower polymerizing cyclic imino ether monomers. In this study we report the effect of the cyclic imino ether structure on the polymerization rate under exactly the same microwave-assisted conditions revealing that indeed less reactive cyclic imino ethers, including 2-oxazines as well as 4- and 5-substituted 2-oxazolines, can be polymerized to at least 50% conversion for the slowest monomer, namely 5-methyl-2-butyl-2-oxazoline, within 10 h. In addition, the copolymerization behavior of 4-ethyl-2-butyl-2-oxazoline with 2-methyl-2-oxazoline and 2-phenyl-2-oxazoline unexpectedly revealed faster incorporation of the less reactive 4-ethy1-2-buty1-2-oxazoline monomer compared to 2-phenyl-2-oxazoline due to the increased bulk of the latter monomer amplifying the sterical hindrance for polymerization onto the 4-ethyl-2-butyl-2-oxazolinium propagating species.
Keywords
2-PHENYL-2-OXAZOLINE, MICROWAVE ACCELERATED POLYMERIZATION, 2-ETHYL-2-OXAZOLINE, POLY(2-OXAZOLINE)S, OXAZOLINES, CHEMISTRY

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Chicago
Lambermont-Thijs, Hanneke ML, Martin WM Fijten, AJ (Ton) van der Linden, Bart M van Lankvelt, Meta M Bloksma, Ulrich S Schubert, and Richard Hoogenboom. 2011. “Efficient Cationic Ring-opening Polymerization of Diverse Cyclic Imino Ethers: Unexpected Copolymerization Behavior.” Macromolecules 44 (11): 4320–4325.
APA
Lambermont-Thijs, H. M., Fijten, M. W., van der Linden, A. (Ton), van Lankvelt, B. M., Bloksma, M. M., Schubert, U. S., & Hoogenboom, R. (2011). Efficient cationic ring-opening polymerization of diverse cyclic imino ethers: unexpected copolymerization behavior. MACROMOLECULES, 44(11), 4320–4325.
Vancouver
1.
Lambermont-Thijs HM, Fijten MW, van der Linden A (Ton), van Lankvelt BM, Bloksma MM, Schubert US, et al. Efficient cationic ring-opening polymerization of diverse cyclic imino ethers: unexpected copolymerization behavior. MACROMOLECULES. 2011;44(11):4320–5.
MLA
Lambermont-Thijs, Hanneke ML, Martin WM Fijten, AJ (Ton) van der Linden, et al. “Efficient Cationic Ring-opening Polymerization of Diverse Cyclic Imino Ethers: Unexpected Copolymerization Behavior.” MACROMOLECULES 44.11 (2011): 4320–4325. Print.
@article{1851510,
  abstract     = {The recently developed fast microwave-assisted cationic ring-opening polymerization procedure for 2-oxazolines seems to be ideally suited for slower polymerizing cyclic imino ether monomers. In this study we report the effect of the cyclic imino ether structure on the polymerization rate under exactly the same microwave-assisted conditions revealing that indeed less reactive cyclic imino ethers, including 2-oxazines as well as 4- and 5-substituted 2-oxazolines, can be polymerized to at least 50\% conversion for the slowest monomer, namely 5-methyl-2-butyl-2-oxazoline, within 10 h. In addition, the copolymerization behavior of 4-ethyl-2-butyl-2-oxazoline with 2-methyl-2-oxazoline and 2-phenyl-2-oxazoline unexpectedly revealed faster incorporation of the less reactive 4-ethy1-2-buty1-2-oxazoline monomer compared to 2-phenyl-2-oxazoline due to the increased bulk of the latter monomer amplifying the sterical hindrance for polymerization onto the 4-ethyl-2-butyl-2-oxazolinium propagating species.},
  author       = {Lambermont-Thijs, Hanneke ML and Fijten, Martin WM and van der Linden, AJ (Ton) and van Lankvelt, Bart M and Bloksma, Meta M and Schubert, Ulrich S and Hoogenboom, Richard},
  issn         = {0024-9297},
  journal      = {MACROMOLECULES},
  keyword      = {2-PHENYL-2-OXAZOLINE,MICROWAVE ACCELERATED POLYMERIZATION,2-ETHYL-2-OXAZOLINE,POLY(2-OXAZOLINE)S,OXAZOLINES,CHEMISTRY},
  language     = {eng},
  number       = {11},
  pages        = {4320--4325},
  title        = {Efficient cationic ring-opening polymerization of diverse cyclic imino ethers: unexpected copolymerization behavior},
  url          = {http://dx.doi.org/10.1021/ma200426y},
  volume       = {44},
  year         = {2011},
}

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