Abstract
The anionic ring-opening copolymerization of L-lactide (LL) with a five-membered cyclic carbonate having the glucopyranoside structure, methyl 4,6-O-benzilidene-2,3-O-carbonyl-α-D-glucopyranoside (MBCG), was carried out using potassium tert-butoxide (t-BuOK) as the initiator and tetrahydrofuran (THF) as the solvent at 30°C for 12h. The mole fractions of LL in the copolymer (fLL) of all copolymers were nearly equal to the corresponding mole fraction of LL in the feed (FLL). Deprotection of the copolymer was performed using trifluoroacetic acid in dichloromethane. 1H NMR spectra of the resulting product indicated that deprotection was completely achieved due to the absence of the aromatic proton signals.
Similar content being viewed by others
Article PDF
References
Z. G. Xie, T. C. Lu, X. S. Chen, C. H. Lu, Y. H. Zheng, and X. B. Jing, J. Appl. Polym. Sci., 105, 2271 (2007).
F. Li, S. M. Li, A. El Ghzaoui, H. Nouailhas, and R. X. Zhuo, Langmuir, 23, 2778 (2007).
Y. Lemmouchi, M. C. Perry, A. J. Amass, K. Chakraborty, and E. Schacht, J. Polym. Sci., Part A: Polym. Chem., 45, 3966 (2007).
C. Deng, X. S. Chen, H. J. Yu, J. Sun, T. C. Lu, and X. B. Jing, Polymer, 48, 139 (2007).
S. S. Venkatraman, P. Jie, F. Min, B. Y. C. Freddy, and G. Leong-Huat, Int. J. Pharm., 298, 219 (2005).
M. Baśko, and P. Kubisa, J. Polym. Sci., Part A: Polym. Chem., 45, 3090 (2007).
F. Fay, E. Renard, V. Langlois, I. Linossier, and K. Vallee-Rehel, Eur. Polym. J., 43, 4800 (2007).
R. Slivniak and A. J. Domb, Biomacromolecules, 6, 1679 (2005).
F. Tasaka, Y. Ohya, and T. Ouchi, Macromol. Rapid Commun., 22, 820 (2001).
J. Helder, F. E. Kohn, S. Sato, J. W. Vandenberg, and J. Feijen, Makromol. Chem., Rapid Commun., 6, 9 (1985).
F. He, Y. P. Wang, G. Liu, H. L. Jia, J. Feng, and R. X. Zhuo, Polymer, 49, 1185 (2008).
X. L. Hu, X. S. Chen, S. Liu, Q. Shi, and X. B. Jing, J. Polym. Sci., Part A: Polym. Chem., 46, 1852 (2008).
X. H. Chen and R. A. Gross, Macromolecules, 32, 308 (1999).
R. Kumar, W. Gao, and R. A. Gross, Macromolecules, 35, 6835 (2002).
B. D. Mullen, C. N. Tang, and R. F. Storey, J. Polym. Sci., Part A: Polym. Chem., 41, 1978 (2003).
O. Haba, H. Tomizuka, and T. Endo, Macromolecules, 38, 3562 (2005).
K. Soga, S. Hosoda, Y. Tazuke, and S. Ikeda, J. Polym. Sci., Part A: Polym. Chem., 15, 219 (1977).
L. Vogdanis and W. Heitz, Makromol. Chem., Rapid Commun., 7, 543 (1986).
L. Vogdanis, B. Martens, H. Uchtmann, F. Hensel, and W. Heitz, Macromol. Chem. Phys., 191, 465 (1990).
J. C. Lee and M. H. Litt, Macromolecules, 33, 1618 (2000).
M. E. Evans, in “Methods in Carbohydrate Chemistry,” R. L. Whistler and J. N. BeMiller, Ed., Academic Press, New York, 1980, Vol. 8, p 313.
W. M. Doane, B. S. Shasha, E. I. Stout, C. R. Russell, and C. E. Rist, Carbohydr. Res., 4, 445 (1967).
H. R. Kricheldorf and I. Kreisersaunders, Macromol. Chem. Phys., 191, 1057 (1990).
Z. Jedlin´ski, W. Walach, P. Kurcok, and G. Adamus, Macromol. Chem. Phys., 192, 2051 (1991).
H. R. Kricheldorf and C. Boettcher, Macromol. Chem. Phys., 194, 1665 (1993).
M. Bero, P. Dobrzynski, and J. Kasperczyk, J. Polym. Sci., Part A: Polym. Chem., 37, 4038 (1999).
M. H. Chisholm, D. Navarro-Llobet, and W. J. Simonsick, Macro-molecules, 34, 8851 (2001).
D. Nagai, M. Nishida, B. Ochiai, K. Miyazaki, and T. Endo, J. Polym. Sci., Part A: Polym. Chem., 44, 3233 (2006).
P. G. M. Wuts, and T. W. Greene, “Greene's Protective Groups in Organic Synthesis,” 4th ed., John Wiley&Sons, New Jersey, 2007, p321.
P. De Santis, and A. J. Kovacs, Biopolymers, 6, 299 (1968).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Haba, O., Furuichi, N. & Akashika, Y. Anionic Ring-Opening Copolymerization of L-Lactide with a Five-Membered Cyclic Carbonate Having a Glucopyranoside Structure. Polym J 41, 702–708 (2009). https://doi.org/10.1295/polymj.PJ2008327
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.PJ2008327
Keywords
This article is cited by
-
Anionic ring-opening polymerization of five-membered cyclic carbonates derived from aldohexopyranosides
Polymer Bulletin (2015)
-
Ring-opening polymerization of a five-membered lactone trans-fused to a cyclohexane ring
Polymer Journal (2014)