Synthesis of polyester having pendent hydroxyl groups via regioselective dehydration polycondensations of dicarboxylic acids and diols by low temperature polycondensation

作者: Yosuke Shibata , Akinori Takasu

DOI: 10.1002/POLA.23619

关键词:

摘要: In this article, we describe the one-step synthesis of polyesters having pendent hydroxyl groups by Lewis acid-catalyzed, regioselective, dehydration polycondensations diols (glycerol and sorbitol) dicarboxylic acids [tartaric acid (TA) malic (MA)] containing groups, using low temperature polycondensation technique. Direct TA or MA 1,9-nonanediol catalyzed scandium trifluoromethanesulfonate [Sc(OTf)3] successfully yielded linear functionality (Mn = ca. 1.0 × 104). To demonstrate reactivity group, a glycosidation was performed. Poly(nonamethylene L-malate) showed significant higher biodegradability, compared with poly(nonamethylene L-tartrate) succinate). Stable emulsion could be prepared poly(vinyl alcohol) as surfactant, although emulsions consisting succinate) were unstable phase-separated within few days. Furthermore, direct diethylene glycol (DEG) triethylene (TEG) produced water-soluble groups. This new system may extremely effective not only for advanced material design functional monomers but also utilization biomass resources chemical substances. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Chem 47: 5747–5759,

参考文章(20)
Akinori Takasu, Yoshitaka Iio, Yoshika Oishi, Yuuki Narukawa, Tadamichi Hirabayashi, Environmentally Benign Polyester Synthesis by Room Temperature Direct Polycondensation of Dicarboxylic Acid and Diol Macromolecules. ,vol. 38, pp. 1048- 1050 ,(2005) , 10.1021/MA0475378
Helen C. Aspinall, Jennifer L. M. Dwyer, Nicholas Greeves, Edward G. McIver, J. Christopher Woolley, Solubilized Lanthanide Triflates: Lewis Acid Catalysis by Polyether and Poly(ethylene glycol) Complexes of Ln(OTf)3 Organometallics. ,vol. 17, pp. 1884- 1888 ,(1998) , 10.1021/OM9709087
Kristien Mortelmans, Errol Zeiger, The Ames Salmonella/microsome mutagenicity assay Mutation Research. ,vol. 455, pp. 29- 60 ,(2000) , 10.1016/S0027-5107(00)00064-6
Jindřich Kopeček, Karel Ulbrich, Biodegradation of biomedical polymers Progress in Polymer Science. ,vol. 9, pp. 1- 58 ,(1983) , 10.1016/0079-6700(83)90005-9
Akinori Takasu, Yoshika Oishi, Yoshitaka Iio, Yoshihito Inai, Tadamichi Hirabayashi, Synthesis of Aliphatic Polyesters by Direct Polyesterification of Dicarboxylic Acids with Diols under Mild Conditions Catalyzed by Reusable Rare-Earth Triflate Macromolecules. ,vol. 36, pp. 1772- 1774 ,(2003) , 10.1021/MA021462V
Akinori Takasu, Yosuke Shibata, Yuuki Narukawa, Tadamichi Hirabayashi, Chemoselective Dehydration Polycondensations of Dicarboxylic Acids and Diols Having Pendant Hydroxyl Groups Using the Room Temperature Polycondensation Technique Macromolecules. ,vol. 40, pp. 151- 153 ,(2007) , 10.1021/MA062514+
Qinghui Hao, Jing Yang, Qiaobo Li, Yang Li, Lin Jia, Qiang Fang, Amin Cao, None, New facile approach to novel water-soluble aliphatic poly(butylene tartarate)s bearing reactive hydroxyl pendant groups. Biomacromolecules. ,vol. 6, pp. 3474- 3480 ,(2005) , 10.1021/BM050317X
Ajay Kumar, Ankur S. Kulshrestha, Wei Gao, Richard A. Gross, Versatile Route to Polyol Polyesters by Lipase Catalysis Macromolecules. ,vol. 36, pp. 8219- 8221 ,(2003) , 10.1021/MA0351827
Nobuyoshi Nomura, Atsuko Taira, Takashi Tomioka, Masahiko Okada, A catalytic approach for cationic living polymerization : Sc(OTf)3-Catalyzed ring-opening polymerization of lactones Macromolecules. ,vol. 33, pp. 1497- 1499 ,(2000) , 10.1021/MA991580R