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Synthesis of PEG‐functionalized poly(diphenylacetylene)s and their gas permeation properties
Author(s) -
Sakaguchi Toshikazu,
Kameoka Koji,
Hashimoto Tamotsu
Publication year - 2009
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.30235
Subject(s) - diphenylacetylene , phenylacetylene , polymer chemistry , diethylene glycol , polyethylene glycol , polymer , peg ratio , trimethylsilyl , materials science , isocyanate , gel permeation chromatography , chemistry , organic chemistry , polyurethane , ethylene glycol , catalysis , finance , economics
Abstract The polymerizations of 1‐(3‐methylphenyl)‐2‐(4‐trimethylsilyl)phenylacetylene ( 1a ) and 1‐(4‐methylphenyl)‐2‐(4‐trimethylsilyl)phenylacetylene ( 1b ) were carried out with TaCl 5 ‐ n ‐Bu 4 Sn to give relatively high‐molecular‐weight polymers ( 2a and 2b ) ( M n > 5 × 10 5 ). The obtained polymers were brominated by using benzoyl peroxide and N ‐bromosuccinimide first, followed by substitution reaction of three types of polyethylene glycol. When diethylene glycol was used as a reagent on substitution reaction of meta‐substituted polymer, PEG‐functionalized poly(diphenylacetylene) with the highest content of oxyethylene unit [ 4a(2) ] was obtained, and the degree of substitution was 0.60. The degrees of substitution decreased to 0.15 and 0.08 when the polyethylene glycols with higher molecular weights were used. PEG‐substitution reaction to the para‐substituted polymers was difficult to proceed, and hence the degree of substitution was 0.18 even when diethylene glycol was used. The CO 2 /N 2 separation factor of PEG‐functionalized polymer [ 4a(2) ] was as large as 28.8, although that of 2a was 7.41. The other PEG‐functionalized polymers also exhibited high CO 2 permselectivity, and their CO 2 /N 2 separation factors were over 20. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009