Chain‐growth condensation polymerization of 4‐aminobenzoic acid esters bearing tri(ethylene glycol) side chain with lithium amide base |
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Authors: | Kazuo Yoshino Kotaro Hachiman Akihiro Yokoyama Tsutomu Yokozawa |
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Institution: | Department of Material and Life Chemistry, Kanagawa University, Rokkakubashi, Kanagawa‐ku, Yokohama 221‐8686, Japan |
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Abstract: | Chain‐growth condensation polymerization of p‐aminobenzoic acid esters 1 bearing a tri(ethylene glycol) monomethyl ether side chain on the nitrogen atom was investigated by using lithium 1,1,1,3,3,3‐hexamethyldisilazide (LiHMDS) as a base. The methyl ester monomer 1a afforded polymer with low molecular weight and a broad molecular weight distribution, whereas the polymerization of the phenyl ester monomer 1b at ?20 °C yielded polymer with controlled molecular weight (Mn = 2800–13,400) and low polydispersity (Mw/Mn = 1.10–1.15). Block copolymerization of 1b and 4‐(octylamino)benzoic acid methyl ester ( 2 ) was further investigated. We found that block copolymer of poly 1b and poly 2 with defined molecular weight and low polydispersity was obtained when the polymerization of 1b was initiated with equimolar LiHMDS at ?20 °C and continued at ?50 °C, followed by addition of 2 and equimolar LiHMDS at ?10 °C. Spherical aggregates were formed when a solution of poly 1b in THF was dropped on a glass plate and dried at room temperature, although the block copolymer of poly 1b and poly 2 did not afford similar aggregates under the same conditions. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 1357–1363, 2010 |
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Keywords: | block copolymers chain‐growth condensation polymerization living polymerization polyamides self‐assembly |
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