Synthesis of α-, ω-, and α,ω-End-Functionalized Poly(n-butyl acrylate)s by Organocatalytic Group Transfer Polymerization Using Functional Initiator and Terminator
2014
Takada, Kenji | Fuchise, Keita | Kubota, Naoya | Ito, Takahiro | Chen, Yougen | Satoh, Toshifumi | Kakuchi, Toyoji
The α-functionalized (hydroxyl, ethynyl, vinyl, and norbornenyl), ω-functionalized (ethynyl, vinyl, hydroxyl, and bromo), and α,ω-functionalized polyacrylates were precisely synthesized by the N-(trimethylsilyl)bis(trifluoroethanesulfonyl)imide (Me₃SiNTf₂)-catalyzed group transfer polymerization (GTP) of n-butyl acrylate (nBA). The α-functionalization and ω-functionalization were carried out using the functional triisopropylsilyl ketene acetal as the initiator (initiation approach) and 2-phenyl acrylate derivatives as the terminator (termination approach) for the organocatalytic GTP, respectively. All the polymerizations precisely occurred and produced well-defined end-functionalized poly(n-butyl acrylate)s which had predictable molecular weights and narrow molecular weight distributions. High-molecular-weight polyacrylates were easily synthesized using both approaches. In addition, the α,ω-functionalized (hetero)telechelic polyacrylates were synthesized by the combination of the initiation and termination approaches. The structure of the obtained polyacrylates and degree of functionalization were confirmed by the ¹H NMR and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDI-TOF MS) measurements. The spectra of the ¹H NMR and MALDI-TOF MS showed that the end-functionalization quantitatively proceeded without any side reactions.
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