Synthesis, characterization and biocompatibility of biodegradable elastomeric poly(ether-ester urethane)s based on poly(3-hydroxybutyrate-co-3- hydroxyhexanoate) and poly(ethylene glycol) via melting polymerization

Zibiao Li, Xiaodi Yang, Linping Wu, Zhifei Chen, Yuting Lin, Kaitian Xu, Guo Qiang Chen

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Poly(ether-ester urethane)s (PUs) multiblock co-polymers were synthesized from telechelic hydroxylated poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) (PHBHHx) and poly(ethylene glycol) (PEG) via a melting polymerization (MP) process using 1,6-hexamethylene diisocyanate (HDI) as a non-toxic coupling agent for the first time. The PHBHHx segments and PEG segments in the multiblock co-polymers behaved as a hard, hydrophobic and a soft, hydrophilic part, respectively. Their chemical structures and molecular characteristics were studied by gel-permeation chromatography (GPC), 1H-NMR and Fourier transform infrared spectroscopy (FT-IR). The PU produced via the MP method showed a higher molecular weight than those resulting from the solvent polymerization (SP) reported previously. Thermal properties showed enhanced thermal stability with semi-crystalline morphology via incorporation of PEG. The segments compositions evaluated from thermogravimetric analysis (TGA) two-step thermal decomposition profiles suggested that MP enhanced the reactivity of PEG compared with the SP process. It was in good agreement with those calculated from 1H-NMR, as well as the precursor feed ratio, respectively. Water contact angle measurements revealed that surface hydrophilicity of the PUs was enhanced by incorporating the PEG segment into PHBHHx polymer backbone. The mechanical properties assessment of the PUs recorded an improved and adjustable ductility and toughness than pure PHBHHx while preserving the tensile strength. Samples synthesized via MP were resistant to hydrolytic and lipase degradation, yet the multiblock co-polymers incorporating the highest amount of PEG degraded at the highest rate. SEM studies revealed that the surface of the PU films became increasingly porous as the degradation proceeded. Implantation of PU in mouse abdominal cavity indicated that tissue regeneration and tissue compatibility of PU film was better than that of PHBHHx-only film.

Original languageEnglish (US)
Pages (from-to)1179-1202
Number of pages24
JournalJournal of Biomaterials Science, Polymer Edition
Volume20
Issue number9
DOIs
StatePublished - May 1 2009

Fingerprint

Ethylene Glycol
Urethane
Biocompatibility
Polymerization
Ether
Freezing
Polyethylene glycols
Ethers
Esters
Melting
Polymers
Hot Temperature
Nuclear magnetic resonance
Degradation
Tissue regeneration
Histocompatibility
Abdominal Cavity
Tensile Strength
Coupling agents
Lipases

All Science Journal Classification (ASJC) codes

  • Biophysics
  • Bioengineering
  • Biomaterials
  • Biomedical Engineering

Cite this

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title = "Synthesis, characterization and biocompatibility of biodegradable elastomeric poly(ether-ester urethane)s based on poly(3-hydroxybutyrate-co-3- hydroxyhexanoate) and poly(ethylene glycol) via melting polymerization",
abstract = "Poly(ether-ester urethane)s (PUs) multiblock co-polymers were synthesized from telechelic hydroxylated poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) (PHBHHx) and poly(ethylene glycol) (PEG) via a melting polymerization (MP) process using 1,6-hexamethylene diisocyanate (HDI) as a non-toxic coupling agent for the first time. The PHBHHx segments and PEG segments in the multiblock co-polymers behaved as a hard, hydrophobic and a soft, hydrophilic part, respectively. Their chemical structures and molecular characteristics were studied by gel-permeation chromatography (GPC), 1H-NMR and Fourier transform infrared spectroscopy (FT-IR). The PU produced via the MP method showed a higher molecular weight than those resulting from the solvent polymerization (SP) reported previously. Thermal properties showed enhanced thermal stability with semi-crystalline morphology via incorporation of PEG. The segments compositions evaluated from thermogravimetric analysis (TGA) two-step thermal decomposition profiles suggested that MP enhanced the reactivity of PEG compared with the SP process. It was in good agreement with those calculated from 1H-NMR, as well as the precursor feed ratio, respectively. Water contact angle measurements revealed that surface hydrophilicity of the PUs was enhanced by incorporating the PEG segment into PHBHHx polymer backbone. The mechanical properties assessment of the PUs recorded an improved and adjustable ductility and toughness than pure PHBHHx while preserving the tensile strength. Samples synthesized via MP were resistant to hydrolytic and lipase degradation, yet the multiblock co-polymers incorporating the highest amount of PEG degraded at the highest rate. SEM studies revealed that the surface of the PU films became increasingly porous as the degradation proceeded. Implantation of PU in mouse abdominal cavity indicated that tissue regeneration and tissue compatibility of PU film was better than that of PHBHHx-only film.",
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Synthesis, characterization and biocompatibility of biodegradable elastomeric poly(ether-ester urethane)s based on poly(3-hydroxybutyrate-co-3- hydroxyhexanoate) and poly(ethylene glycol) via melting polymerization. / Li, Zibiao; Yang, Xiaodi; Wu, Linping; Chen, Zhifei; Lin, Yuting; Xu, Kaitian; Chen, Guo Qiang.

In: Journal of Biomaterials Science, Polymer Edition, Vol. 20, No. 9, 01.05.2009, p. 1179-1202.

Research output: Contribution to journalArticle

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T1 - Synthesis, characterization and biocompatibility of biodegradable elastomeric poly(ether-ester urethane)s based on poly(3-hydroxybutyrate-co-3- hydroxyhexanoate) and poly(ethylene glycol) via melting polymerization

AU - Li, Zibiao

AU - Yang, Xiaodi

AU - Wu, Linping

AU - Chen, Zhifei

AU - Lin, Yuting

AU - Xu, Kaitian

AU - Chen, Guo Qiang

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