Synthesis of well‐defined,soluble poly(3‐alkyl‐4‐benzamide) by chain‐growth condensation polymerization |
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| Authors: | Yoshihiro Ohta Makoto Karasawa Tetsurou Niiyama Akihiro Yokoyama Tsutomu Yokozawa |
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| Institution: | 1. Department of Material and Life Chemistry, Kanagawa University, , Rokkakubashi, Kanagawa‐ku, Yokohama, 221‐8686 Japan;2. Present Address: Department of Material and Life Science, Seikei University, , Kichijoji‐Kitamachi, Musashino‐shi, Tokyo, 180‐8633 Japan |
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| Abstract: | Well‐defined poly(3‐alkyl‐4‐benzamide) was synthesized by means of chain‐growth condensation polymerization of phenyl 3‐octyl‐4‐(4‐octyloxybenzyl(OOB)amino)benzoate ( 1c ) from initiator 2 , followed by removal of the OOB groups on amide nitrogen of poly 1c . Polymerization of 1c with phenyl 4‐(trifluoromethyl)benzoate ( 2b ) in the presence of 1,1,1,3,3,3‐hexamethyldisilazide (LiHMDS) and LiCl in THF at ?10 °C gave poly 1c with a narrow molecular weight distribution (Mw/Mn ≤ 1.08) and a well‐defined molecular weight (Mn = 4480–12,700) determined by the feed ratio of monomer to initiator (from 10 to 30). The OOB groups of poly 1c were removed with H2SO4 to give the corresponding N‐unsubstituted poly(p‐benzamide) (poly 1c′ ) with low polydispersity. The solublity of poly 1c′ in polar organic solvents was dramatically higher than that of poly(p‐benzamide), demonstrating that introduction of an alkyl group on the aromatic ring is very effective for improving the solubility of poly(p‐benzamide). © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 360–365 |
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| Keywords: | chain‐growth condensation polymerization hydrogen bonding living polymerization molecular weight distribution polyamides solubility |
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