Journal
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 47, Issue 21, Pages 5747-5759Publisher
WILEY
DOI: 10.1002/pola.23619
Keywords
biodegradable; catalysts; chemoselective dehydration polycondensation; polyester; step-growth polymerization; water-soluble
Categories
Funding
- Nagoya Institute of Technology's Research Promotion Program
Ask authors/readers for more resources
In this article, we describe the one-step synthesis of polyesters having pendent hydroxyl groups by Lewis acid-catalyzed, regioselective, dehydration polycondensations of diols (glycerol and sorbitol) and dicarboxylic acids [tartaric acid (TA) and malic acid (MA)] containing pendent hydroxyl groups, using low temperature polycondensation technique. Direct polycondensations of TA or MA and 1,9-non-anediol catalyzed by scandium trifluoromethanesulfonate [Sc(OTf)(3)] successfully yielded linear polyesters having hydroxyl functionality (M-n = ca. 1.0 X 10(4)). To demonstrate the reactivity of the pendent hydroxyl group, a glycosidation was performed. Poly(nonamethylene L-malate) showed significant higher biodegradability, compared with poly(nonamethylene L-tartrate) or poly(nonamethylene succinate). Stable poly(nonamethylene L-tartrate) emulsion could be prepared using poly(vinyl alcohol) as the surfactant, although emulsions consisting of poly(nonamethylene succinate) were unstable and phase-separated within a few days. Furthermore, direct polycondensations of TA and diethylene glycol (DEG) or triethylene glycol (TEG) successfully produced water-soluble polyesters having hydroxyl groups. This new polycondensation system may be extremely effective not only for advanced material design using functional monomers but also for effective utilization of biomass resources as chemical substances. (C) 2009 Wiley Periodicals, Inc. J Polyrn Sci Part A: Polym Chem 47:5747-5759, 2009
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available