JOURNAL OF POLYMER SCIENCE: PART A: POLYMER CHEMISTRY DOI 10.1002/POLA
condensation agent in the presence of DMAP has been dem-
onstrated to accomplish a facile mode of amino acid esterifi-
cation of EC without any polymer chain cleavage in the
course of the reaction. The bulk of the substituent on the
a-carbon of the amino acid pendants was revealed to be the
most significant parameter effecting the extent of substitu-
11 Wang, Y.; Easteal, A. J. J Membr Sci 1999, 157, 53–61.
2 Li, X.-G.; Huang, M.-R.; Hu, L.; Lin, G.; Yang, P.-C. Eur Polym
J 1999, 35, 157–166.
1
1
3 He, Y.; Yang, J.; Li, H.; Huang, P. Polymer 1998, 39,
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393–3397.
1
4 Li, X.-G.; Huang, M.-R. J Appl Polym Sci 1997, 66,
tion of the hydroxy protons of EC (DS , 2.69), and complete
Et
2
139–2147.
incorporation of amino acid functionalities (DSEst ꢄ 100%)
was observed for t-Boc-protected glycine and alanine in the
presence of EDCꢃHCl. Moreover, complete esterification could
also be attained for serine by using its activated ester, as evi-
15 Houde, A. Y.; Stern, S. A. J Membr Sci 1997, 127, 171–183.
1
6 Suto, S.; Niimi, T.; Sugiura, T. J Appl Polym Sci 1996, 61,
1
621–1630.
1
denced by H NMR. The esterification of EC with bulky
1
7 Houde, A. Y.; Stern, S. A. J Membr Sci 1994, 92, 95–101.
organic moieties resulted in enhanced solubility in common
organic solvents, notably in acetone. Fair thermal stability
was revealed, and initiation of weight loss was elucidated to
18 Baughman, T. W.; Wagener, K. B. Adv Polym Sci 2005, 176,
1–42.
ensue from the degradation of t-butyl moieties around
1
9 Okoshi, K.; Sakajiri, K.; Kumaki, J.; Yashima, E. Macromole-
ꢀ
200 C in air. The amino acid functionalization of EC accom-
cules 2005, 38, 4061–4064.
panied the lowering of glass transition temperature. Free-
standing membranes were fabricated by solution casting,
and the presence of polar groups led to the decreased gas
permeability, due to the augmented interactions and thus
reduced free volume space inside the polymer matrix, along
2
0 Vriezema, D. M.; Kros, A.; de Gelder, R.; Cornelissen, J.;
Rowan, A. E.; Nolte, R. J. M. Macromolecules 2004, 37,
4
736–4739.
2
1 Vriezema, D. M.; Hoogboom, J.; Velonia, K.; Takazawa, K.;
Christianen, P. C. M.; Maan, J. C.; Rowan, A. E.; Nolte, R. J. M.
Angew Chem Int Ed 2003, 42, 772–776.
with the improved/increased CO permselectivity.
2
The authors express their sincere gratitude for financial sup-
port by the Research Institute of Innovative Technology for
the Earth (RITE), The Sumitomo Foundation (No. 073328),
and The Nissan Science Foundation.
2
2 Katsarava, R. Macromol Symp 2003, 199, 419–429.
2
3 Vandermeulen, G. W. M.; Tziatzios, C.; Klok, H.-A. Macromo-
lecules 2003, 36, 4107–4114.
2
4 Checot, F.; Lecommandoux, S.; Gnanou, Y.; Klok, H.-A.
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