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Cited by 144biodegradable polymer synthesis and propertiesAdvanced Polymer Synthesis and CharacterizationAdvanced Drug Delivery Systems

The DOI matches its Crossref record; 15 of the 15 references it cites were found in a registry or an index.

Ring-Opening Polymerization of 1,4,8-Trioxaspiro[4.6]-9-undecanone: A New Route to Aliphatic Polyesters Bearing Functional Pendent Groups

Tian, Dong, Dubois, Philippe, Grandfils, Christian, Jérôme, Robert·1997·Macromolecules
DOI 10.1021/ma961631+
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Abstract

A straightforward and very efficient pathway has been reported for the synthesis of a functional derivative of ε-caprolactone, i.e. 5-ethylene ketal ε-caprolactone. This new monomer has been homopolymerized and copolymerized with ε-caprolactone in a well-controlled manner, strongly suggesting absence of any side reactions. Deacetalization of the polyester chains is complete and reduction of the ketone groups into hydroxyl groups as well. No chain scission is observed to occur in the course of these two derivatization reactions. Thus, aliphatic polyesters bearing either ketone pendent groups or hydroxyl pendent groups can be easily prepared, which raises new application prospects. These materials proved to be easily redispersed in an aqueous medium. They form stable colloidal nanodispersions (e.g. 100 nm). These suspensions are stable more than 48 h at room temperature and may be viewed as potential drug colloidal vectors with a core−shell like structure. Different types of reactive groups on the surface of these nanoparticulate vectors are indeed available to the binding of species selected for molecular recognition and drug targeting. For instance, the well-known reactivity of ketones toward primary amines is a direct route to attach peptides onto biodegradable and biocompatible aliphatic polyesters. Poly(ε-caprolactone) with hydroxyl groups reactive toward triethylaluminum provides a macroinitiator for lactone and lactide polymerization, so that biodegradable and biocompatible functional comb, graft, and dendritic aliphatic polyesters can now be synthesized.

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Crossref · 10.1021/ma961631+

Cites

15 of 15 references verified0 citation errors · 0 not checkable

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  • Ketal groups in the γ-ketal lactone polymer are used as protected ketones, whose reduction by sodium borohydride led to pendent hydroxyl groups, together with an increase of the hydrophilic character of the hydroxy-polyester.

    “The ketal groups are used as protected ketones, whose reduction by sodium borohydride led to pendent hydroxyl groups, together with an increase of the hydrophilic character of the hydroxy-polyester.”

    From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [101]

  • 1,4,8-trioxaspiro[4.6]-9-undecanone is homo-polymerized and copolymerized with ε-caprolactone.

    “This γ-ketal lactone is homo-polymerized [101] and copolymerized [102] with ε-caprolactone.”

    From Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization☆ (2008) · cites this paper as [101]

Citations

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Research works printed but not linked: 5

  1. Pitt C. G., 1980, Biodegradable Drug Delivery Systems based on Aliphatic Polyester: Application of Contraceptives and Narcotic Antagonists In Controlled Release of Bioactive Materials
  2. Vert M., 1979, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 20, 608
  3. Braud C., 1988, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 29, 600
  4. Arnold S. C., 1986, Macromol. Symp.
  5. Sepulchre M. O., 1994, Macromol. Rep., 31, 1085

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Metadata

Authors
Tian, D., Dubois, P., Grandfils, C., & Jérôme, R.
Affiliations
  • University of Liège (BE)
  • Center for Education and Research on Macromolecules (CERM), University of Liège, Sart-Tilman, B6, 4000 Liège, Belgium
ORCID
Grandfils, Christian
Venue
Macromolecules
Publisher
American Chemical Society (ACS)
Published
1997-02-01
Volume
30
Issue
3
Pages
406-409
ISSN
  • 0024-9297 (ISSN-L)
  • 1520-5835
DOI
10.1021/ma961631+
OpenAlex
W2030275481
Cited by
140
References
15
Citations by year
2025: 2 · 2024: 1 · 2023: 3 · 2022: 3 · 2020: 2 · 2019: 2 · 2018: 5 · 2017: 3 · 2016: 3 · 2015: 4 · 2014: 2 · 2013: 4 · 2012: 11
FWCI
5.62
Type
journal article
Language
en
Open access
closed
Locations
  • Macromolecules (publishedVersion)
  • ORBi (University of Liège) (submittedVersion)
Topics
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
  • Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Advanced Drug Delivery Systems
Keywords
ring-opening polymerization, aliphatic polyesters, deacetalization, ketone reduction, aqueous dispersion stability, drug delivery vectors, peptide conjugation, biodegradable polyesters

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