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Cited by 62biodegradable polymer synthesis and propertiesPolymer crystallization and propertiesPolymer composites and self-healing

Synthesis and Characterization of Poly(butylene succinate-co-butylene malate): A New Biodegradable Copolyester Bearing Hydroxyl Pendant Groups

Zhang, Shiping, Yang, Jing, Liu, Xiaoyun, Chang, Jianhua, Cao, Amin·2003·Biomacromolecules
DOI 10.1021/bm0201183
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Abstract

A new biodegradable copolyester, poly(butylene succinate-co-butylene malate) P(BS-co-BM), has been preliminarily prepared with optically active centers and lateral hydroxyl functional groups via a four-step synthetic strategy. First, an optically active benzyl-protected dimethyl malate was synthesized from a starting material of (S)-dimethyl malate and purified with good yield. Then, copolyester poly(butylene succinate-co-benzyl-protected butylene malate), P(BS-co-BBM), was prepared through a skilled condensation copolymerization of the benzyl-protected dimethyl malate, dimethyl succinate, and 1,4-butanediol in the presence of titanium tetraisopropoxide as the catalyst. Finally, a Pd/C catalyzed hydrogenation was applied to eliminate the benzyl protection group in a mixed solution of THF and methanol; thus the target copolyester P(BS-co-BM) was attained. On the other hand, physical properties of the synthesized copolyesters were systematically characterized by means of nuclear magnetic resonance spectrometer, Fourier transformed infrared spectrometer, gel permeation chromatography, optical polarimeter, quantitative hydroxyl titration, and thermal analytical instruments. The experimental evidence demonstrated a successful construction of the product P(BS-co-BM) bearing lateral hydroxyl functional groups. It was also revealed that the lower BBM unit content was in the benzyl-protected optically active P(BS-co-BBM) copolyester, the higher melting point T(m), crystallinity, the broader molecular distribution, and the lower glass transition temperature T(g) would be detected, and these results can be accounted for the presence of bulky lateral benzyl moieties. In contrast, the deprotected product P(BS-co-55 mol % BM) showed a higher T(m), crystallinity and lower T(g) than its counterpart P(BS-co-55 mol % BBM). Interestingly, a thermal stability as high as that of the linear PBS was observed for P(BS-co-55 mol % BM) while a strong BBM unit content dependence of thermal stability was detected for the benzyl-protected copolyester P(BS-co-BBM)s. Therefore, these results may be beneficial for the new optically active P(BS-co-BM) bearing hydrophilic hydroxyl functional groups as a potential biomaterial.

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  • The use of a chemoselective catalyst is critical to eliminate the need for tedious and uneconomical protection chemistry and to enhance product specificity.

    “The use of a chemoselective catalyst is critical to eliminate the need for tedious and uneconomical protection chemistry 239,240 and to enhance the product specificity.”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [239]

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Authors
Zhang, S., Yang, J., Liu, X., Chang, J., & Cao, A.
Affiliations
  • Chinese Academy of Sciences (CN)
  • Polymer Materials Lab, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Street, Shanghai 200032, People's Republic of China, and Department of Chemistry, Northwest University, 229 North Taibai Road, Xi'an, Shanxi 710069, People's Republic of China
ORCID
Venue
Biomacromolecules
Publisher
American Chemical Society (ACS)
Published
2003-02-13
Volume
4
Issue
2
Pages
437-445
ISSN
  • 1525-7797 (ISSN-L)
  • 1526-4602
DOI
10.1021/bm0201183
OpenAlex
W2061944824
Cited by
62
References
30
Citations by year
2025: 1 · 2023: 2 · 2022: 3 · 2021: 1 · 2020: 4 · 2019: 2 · 2018: 7 · 2017: 5 · 2016: 2 · 2015: 3 · 2014: 1 · 2013: 4 · 2012: 3
FWCI
1.42
Type
journal article
Language
en
Open access
closed
Locations
  • Biomacromolecules (publishedVersion)
  • PubMed (publishedVersion)
Funders
National Science Foundation
Topics
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
Keywords
biodegradable copolyesters, thermal stability, crystallinity, glass transition temperature, biomaterials
MeSH terms
Biodegradation, Environmental, Chromatography, Gas, Magnetic Resonance Spectroscopy, Polyesters, Spectrophotometry, Infrared, Hydroxyl Radical

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