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Full and partial amidation of poly(methyl acrylate) as basis for functional polyacrylamide (co)polymers

Joachim Van Guyse (UGent) , Jente Verjans (UGent) , Stef Vandewalle (UGent) , Kevin De Bruycker (UGent) , Filip Du Prez (UGent) and Richard Hoogenboom (UGent)
(2019) MACROMOLECULES. 52(14). p.5102-5109
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Abstract
The direct modification of poly(methyl acrylate) (PMA) to obtain functional poly(acrylate ester)s or poly(N-alkyl acrylamide)s is generally considered to be an inefficient approach. Only in recent years, several research groups reported the possibility of the direct modification of unactivated poly(acrylate ester)s in order to obtain functional structures. Within this contribution, we explored the amidation kinetics of PMA with five different amines, utilizing triazabicyclodecene (TBD) as an organocatalyst. We demonstrate that the reaction conditions can be tuned to provide kinetic control over the functionalization degree of the polymer. The reaction kinetics revealed that amine nucleophilicity plays a larger role at the initial stages of the reaction, while steric factors and polymer solvation dominate the reaction kinetics at later stages. Finally, we demonstrate the utility of the developed approach to synthesize functional polymers with olefin side chains, which were subsequently crosslinked via thiol-ene and Alder-ene chemistry.
Keywords
CROSS-LINKING, SELECTIVE TRANSESTERIFICATION, POLYMERS, POLYMERIZATION, COPOLYMERS, CHEMISTRY, POSTFUNCTIONALIZATION, POLY(2-OXAZOLINE)S, TRIAZOLINEDIONES, ULTRAFAST

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MLA
Van Guyse, Joachim, et al. “Full and Partial Amidation of Poly(Methyl Acrylate) as Basis for Functional Polyacrylamide (Co)Polymers.” MACROMOLECULES, vol. 52, no. 14, 2019, pp. 5102–09.
APA
Van Guyse, J., Verjans, J., Vandewalle, S., De Bruycker, K., Du Prez, F., & Hoogenboom, R. (2019). Full and partial amidation of poly(methyl acrylate) as basis for functional polyacrylamide (co)polymers. MACROMOLECULES, 52(14), 5102–5109.
Chicago author-date
Van Guyse, Joachim, Jente Verjans, Stef Vandewalle, Kevin De Bruycker, Filip Du Prez, and Richard Hoogenboom. 2019. “Full and Partial Amidation of Poly(Methyl Acrylate) as Basis for Functional Polyacrylamide (Co)Polymers.” MACROMOLECULES 52 (14): 5102–9.
Chicago author-date (all authors)
Van Guyse, Joachim, Jente Verjans, Stef Vandewalle, Kevin De Bruycker, Filip Du Prez, and Richard Hoogenboom. 2019. “Full and Partial Amidation of Poly(Methyl Acrylate) as Basis for Functional Polyacrylamide (Co)Polymers.” MACROMOLECULES 52 (14): 5102–5109.
Vancouver
1.
Van Guyse J, Verjans J, Vandewalle S, De Bruycker K, Du Prez F, Hoogenboom R. Full and partial amidation of poly(methyl acrylate) as basis for functional polyacrylamide (co)polymers. MACROMOLECULES. 2019;52(14):5102–9.
IEEE
[1]
J. Van Guyse, J. Verjans, S. Vandewalle, K. De Bruycker, F. Du Prez, and R. Hoogenboom, “Full and partial amidation of poly(methyl acrylate) as basis for functional polyacrylamide (co)polymers,” MACROMOLECULES, vol. 52, no. 14, pp. 5102–5109, 2019.
@article{8621917,
  abstract     = {The direct modification of poly(methyl acrylate) (PMA) to obtain functional poly(acrylate ester)s or poly(N-alkyl acrylamide)s is generally considered to be an inefficient approach. Only in recent years, several research groups reported the possibility of the direct modification of unactivated poly(acrylate ester)s in order to obtain functional structures. Within this contribution, we explored the amidation kinetics of PMA with five different amines, utilizing triazabicyclodecene (TBD) as an organocatalyst. We demonstrate that the reaction conditions can be tuned to provide kinetic control over the functionalization degree of the polymer. The reaction kinetics revealed that amine nucleophilicity plays a larger role at the initial stages of the reaction, while steric factors and polymer solvation dominate the reaction kinetics at later stages. Finally, we demonstrate the utility of the developed approach to synthesize functional polymers with olefin side chains, which were subsequently crosslinked via thiol-ene and Alder-ene chemistry.},
  author       = {Van Guyse, Joachim and Verjans, Jente and Vandewalle, Stef and De Bruycker, Kevin and Du Prez, Filip and Hoogenboom, Richard},
  issn         = {0024-9297},
  journal      = {MACROMOLECULES},
  keywords     = {CROSS-LINKING,SELECTIVE TRANSESTERIFICATION,POLYMERS,POLYMERIZATION,COPOLYMERS,CHEMISTRY,POSTFUNCTIONALIZATION,POLY(2-OXAZOLINE)S,TRIAZOLINEDIONES,ULTRAFAST},
  language     = {eng},
  number       = {14},
  pages        = {5102--5109},
  title        = {Full and partial amidation of poly(methyl acrylate) as basis for functional polyacrylamide (co)polymers},
  url          = {http://dx.doi.org/10.1021/acs.macromol.9b00399},
  volume       = {52},
  year         = {2019},
}

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