Synthesis and characterization of biobased isosorbide-containing copolyesters as shape memory polymers for biomedical applications.

Novel biobased isosorbide-containing copolyesters (PBISI copolyesters) with both biocompatibility and sustainability were synthesized by using commercially available biobased diols and diacids. Due to the presence of itaconate in copolyesters, it can be readily crosslinked by peroxide into a crystallizable network. The structure and thermal properties of PBISI copolyesters were determined by 1H NMR, FTIR, DSC, and WAXD. The chain composition, melting point and crystallinity of the PBISI copolyesters can be tuned continuously by changing the content of isosorbide. The crosslinked copolyester is demonstrated to be a promising shape memory polymer (SMP) with excellent shape memory properties including shape fixity and shape recovery rate close to 100%. The switching temperatures of PBISI-based SMPs can be tuned between 26 °C and 54 °C by altering the composition of PBISI copolyesters and curing extent. Cell adhesion and proliferation were adopted to evaluate the potential biocompatibility of PBISI-based SMPs, and the results indicated that all the PBISI-based SMPs were essentially noncytotoxic, making them suitable for fabricating biomedical devices.

[1]  Liang Xue,et al.  Synthesis and Characterization of Three-Arm Poly(ε-caprolactone)-Based Poly(ester−urethanes) with Shape-Memory Effect at Body Temperature , 2009 .

[2]  A. Loupy,et al.  Characterization of cyclic and non-cyclic poly-(ether-urethane)s bio-based sugar diols by a combination of MALDI-TOF and NMR , 2007 .

[3]  H. Sung,et al.  Mechanical properties of a porcine aortic valve fixed with a naturally occurring crosslinking agent. , 1999, Biomaterials.

[4]  A. Schmidt.  Electromagnetic Activation of Shape Memory Polymer Networks Containing Magnetic Nanoparticles , 2006 .

[5]  Patrick T. Mather,et al.  Chemically Cross-Linked Polycyclooctene: Synthesis, Characterization, and Shape Memory Behavior , 2002 .

[6]  Liang Xue,et al.  Biodegradable shape-memory block co-polymers for fast self-expandable stents. , 2010, Biomaterials.

[7]  Andreas Lendlein,et al.  Kinetics and dynamics of thermally-induced shape-memory behavior of crosslinked short-chain branched polyethylenes , 2009 .

[8]  Liqun Zhang,et al.  Vapor grown carbon nanofiber reinforced bio-based polyester for electroactive shape memory performance , 2013 .

[9]  Thrimoorthy Potta,et al.  Injectable, dual cross-linkable polyphosphazene blend hydrogels. , 2010, Biomaterials.

[10]  Li Liu,et al.  Preparation and characterization of high strength and noncytotoxic bioelastomers containing isosorbide , 2014 .

[11]  Donald Garlotta,et al.  A Literature Review of Poly(Lactic Acid) , 2001 .

[12]  Liqun Zhang,et al.  Biobased poly(propylene sebacate) as shape memory polymer with tunable switching temperature for potential biomedical applications. , 2011, Biomacromolecules.

[13]  A. M. D. Ilarduya,et al.  Bio-based aromatic copolyesters made from 1,6-hexanediol and bicyclic diacetalized D-glucitol , 2012 .

[14]  R. Langer,et al.  Light-induced shape-memory polymers , 2005, Nature.

[15]  A. Rozanski,et al.  Semicrystalline Polyesters Based on a Novel Renewable Building Block , 2012 .

[16]  R. Duchateau,et al.  Incorporation of isosorbide into poly(butylene terephthalate) via solid-state polymerization. , 2008, Biomacromolecules.

[17]  Liqun Zhang,et al.  Synthesis and characterization of novel soybean-oil-based elastomers with favorable processability and tunable properties , 2012 .

[18]  S. Chatti,et al.  Cyclic and Noncyclic Polycarbonates of Isosorbide (1,4:3,6-Dianhydro-d-glucitol) , 2006 .

[19]  Andreas Heise,et al.  Co- and terpolyesters based on isosorbide and succinic acid for coating applications: synthesis and characterization. , 2006, Biomacromolecules.

[20]  J. Hu,et al.  Effect of soft segment crystallization and hard segment physical crosslink on shape memory function in antibacterial segmented polyurethane ionomers. , 2009, Acta biomaterialia.

[21]  Andrew G. Glen,et al.  APPL , 2001 .

[22]  A. M. D. Ilarduya,et al.  D-Glucose-derived PET copolyesters with enhanced Tg , 2013 .

[23]  M. Ballauff,et al.  Synthesis and thermal analysis of copolyesters deriving from 1,4:3,6-dianhydrosorbitol, ethylene glycol, and terephthalic acid , 1996 .

[24]  R. Duchateau,et al.  Enhancing the functionality of biobased polyester coating resins through modification with citric acid. , 2007, Biomacromolecules.

[25]  Rashmi,et al.  Polyhydroxyalkanoates: an overview. , 2003, Bioresource technology.

[26]  Liqun Zhang,et al.  Design and Preparation of a Novel Cross-Linkable, High Molecular Weight, and Bio-Based Elastomer by Emulsion Polymerization , 2012 .

[27]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[28]  Wei Min Huang,et al.  Water-driven programmable polyurethane shape memory polymer: Demonstration and mechanism , 2005 .

[29]  S. Swain,et al.  Biodegradable Soy-Based Plastics: Opportunities and Challenges , 2004 .

[30]  A. Lendlein,et al.  Multifunctional Shape‐Memory Polymers , 2010, Advanced materials.

[31]  Andreas Lendlein,et al.  Biodegradable, amorphous copolyester-urethane networks having shape-memory properties. , 2005, Angewandte Chemie.

[32]  A. Gandini,et al.  Materials from renewable resources based on furan monomers and furan chemistry: work in progress , 2009 .

[33]  Liqun Zhang,et al.  Tough Bio‐Based Elastomer Nanocomposites with High Performance for Engineering Applications , 2012 .

[34]  H. Kricheldorf,et al.  Influence of Isosorbide on Glass‐Transition Temperature and Crystallinity of Poly(butylene terephthalate) , 2007 .

[35]  Y. Ohya,et al.  Biodegradable shape-memory polymers exhibiting sharp thermal transitions and controlled drug release. , 2009, Biomacromolecules.

[36]  J. Pascault,et al.  Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review , 2010 .

[37]  Daan S. van Es,et al.  Novel, Fully Biobased Semicrystalline Polyamides , 2011 .