Synthesis and characterization of novel biodegradable aliphatic poly(ester amide)s containing cyclohexane units

Hélène A. Lecomte, J.J. Liggat, Adam S.G. Curtis

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Polyesters provide a good basis to work on for designing novel biodegradable materials that are also mechanically and thermally resistant. In this study, a series of aliphatic poly(ester amide)s (PEA) based on cyclohexane units was synthesized. Block-copolymers of cyclohexyl sebacate and cyclohexyl sebacamide were produced by controlling the length of the ester block and the amount of amide during a two-step melt/interfacial polycondensation reaction. Films produced from these materials could retain their shape above 373 K due to the physical network of amide hydrogen-bonding. Thermal properties were also evaluated, with various melting and softening points obtained depending on the PEA composition. The determining factor for mechanical properties was the amount of amide introduced, with films containing up to 10 mol % amide showing the best handleability and flexibility. Tensile properties typical of an amorphous viscoelastic material were observed, but with much superior elongation to break achievable (1700%). These materials were also shown to be hydrolyzable, noncytotoxic, and favorable for cell attachment: they may therefore have a promising future in the area of medical devices or packaging, especially as their properties can be tuned by changing their composition.
LanguageEnglish
Pages1785-1795
Number of pages11
JournalJournal of Polymer Science Part A: Polymer Chemistry
Volume44
Issue number6
DOIs
Publication statusPublished - 15 Mar 2006

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Cyclohexane
Amides
Esters
Interfacial polycondensation
Polyesters
Chemical analysis
Tensile properties
Block copolymers
Elongation
Packaging
Hydrogen bonds
Melting
Thermodynamic properties
Mechanical properties

Keywords

  • biocompatibility
  • biodegradable
  • polyesters
  • polyamides
  • synthesis

Cite this

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title = "Synthesis and characterization of novel biodegradable aliphatic poly(ester amide)s containing cyclohexane units",
abstract = "Polyesters provide a good basis to work on for designing novel biodegradable materials that are also mechanically and thermally resistant. In this study, a series of aliphatic poly(ester amide)s (PEA) based on cyclohexane units was synthesized. Block-copolymers of cyclohexyl sebacate and cyclohexyl sebacamide were produced by controlling the length of the ester block and the amount of amide during a two-step melt/interfacial polycondensation reaction. Films produced from these materials could retain their shape above 373 K due to the physical network of amide hydrogen-bonding. Thermal properties were also evaluated, with various melting and softening points obtained depending on the PEA composition. The determining factor for mechanical properties was the amount of amide introduced, with films containing up to 10 mol {\%} amide showing the best handleability and flexibility. Tensile properties typical of an amorphous viscoelastic material were observed, but with much superior elongation to break achievable (1700{\%}). These materials were also shown to be hydrolyzable, noncytotoxic, and favorable for cell attachment: they may therefore have a promising future in the area of medical devices or packaging, especially as their properties can be tuned by changing their composition.",
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Synthesis and characterization of novel biodegradable aliphatic poly(ester amide)s containing cyclohexane units. / Lecomte, Hélène A.; Liggat, J.J.; Curtis, Adam S.G.

In: Journal of Polymer Science Part A: Polymer Chemistry, Vol. 44, No. 6, 15.03.2006, p. 1785-1795.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Lecomte, Hélène A.

AU - Liggat, J.J.

AU - Curtis, Adam S.G.

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AB - Polyesters provide a good basis to work on for designing novel biodegradable materials that are also mechanically and thermally resistant. In this study, a series of aliphatic poly(ester amide)s (PEA) based on cyclohexane units was synthesized. Block-copolymers of cyclohexyl sebacate and cyclohexyl sebacamide were produced by controlling the length of the ester block and the amount of amide during a two-step melt/interfacial polycondensation reaction. Films produced from these materials could retain their shape above 373 K due to the physical network of amide hydrogen-bonding. Thermal properties were also evaluated, with various melting and softening points obtained depending on the PEA composition. The determining factor for mechanical properties was the amount of amide introduced, with films containing up to 10 mol % amide showing the best handleability and flexibility. Tensile properties typical of an amorphous viscoelastic material were observed, but with much superior elongation to break achievable (1700%). These materials were also shown to be hydrolyzable, noncytotoxic, and favorable for cell attachment: they may therefore have a promising future in the area of medical devices or packaging, especially as their properties can be tuned by changing their composition.

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