4-Vinylphenyl Glycidyl Ether: Synthesis, RAFT Polymerization, and Postpolymerization Modifications with Alcohols
4-Vinylphenyl glycidyl ether (4VPGE), an epoxide-containing styrenic monomer, was synthesized and then polymerized in a controlled fashion under reversible addition-fragmentation chain-transfer (RAFT) polymerization conditions using butyl 1-phenylethyl trithiocarbonate as the chain-transfer agent. The high degree of chain-end functionalization of the produced polymers was confirmed by chain extension reactions with styrene that afforded well-defined block copolymers. Phenyl glycidyl ether was utilized as a model compound to identify the optimal reaction conditions for alcoholysis of the glycidyl moiety using BF3 as a Lewis acid catalyst, and postpolymerization modifications were subsequently carried out on the epoxide groups of poly4VPGE with a library of structurally diverse alcohols to yield a number of β-hydroxy ether-functionalized polymers.
McLeod, David C.,Tsarevsky, Nicolay V.
p. 1135 - 1142
(2016/03/25)
METHOD FOR PREPARING GLYCIDYLOXYSTYRENE MONOMERS AND POLYMERS THEREOF
It was found that glycidyloxystyrenes, including glycidyloxystyrene and substituted glycidyloxystyrene, can be synthesized from hydroxycinnamic acid or substituted hydroxycinnamic acids in a one-pot, two-step process. The substrate can be thermally decarboxylated and then without purification, reacted in the presence of a halomethyl-oxirane and a base. The resulting product can be polymerized or coppolymerized to a fully substituted product.
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(2008/12/06)
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