Synthesis and properties of biodegradable elastomeric epoxy modified polyurethanes based on poly(ε-caprolactone) and poly(ethylene glycol)

Abstract Biodegradable polyurethane elastomers with potential for applications in medical implants with tunable degradation rate and physical properties were synthesized from reaction of epoxy terminated polyurethanes (EUP) with 1,6-hexamethylene diamine (HMDA) as curing agent. Poly( e -caprolactone) (PCL) and poly(ethylene glycol) (PEG) as well as 1,6-hexamethylene diisocyanate (HDI) were used for preparation of isocyanate terminated polyurethanes which were subsequently blocked with glycidol to prepare EUPs. All materials were characterized by conventional methods, and their properties were studied fully. Results showed that elastomers based on PEG exhibit superior degradation rate and inferior mechanical properties in comparison to elastomers based on PCL. Optimum degradation rate and mechanical properties were obtained from elastomers made from mixture of PCL and PEG base EUPs.

[1]  S. F. Zawadzki,et al.  Polycaprolactone based biodegradable polyurethanes , 2003 .

[2]  Y. Inoue,et al.  Structure and physical properties of bacterially synthesized polyesters , 1992 .

[3]  Mauli Agrawal,et al.  Synthetic Bioabsorbable Polymers for Implants , 2000 .

[4]  Joseph Kost,et al.  Handbook of Biodegradable Polymers , 1998 .

[5]  D. J. Hourston,et al.  Polyurethane-polysiloxane interpenetrating polymer networks: 1. A polyether urethane-poly(dimethylsiloxane) system , 1984 .

[6]  S. Kansara,et al.  THE EFFECT OF CHAIN LENGTH OF POLYETHYLENE GLYCOL ON PROPERTIES OF CASTOR OIL BASED POLYURETHANE ELASTOMERS , 2002 .

[7]  K. Woodhouse,et al.  Synthesis and characterization of degradable polyurethane elastomers containing and amino acid-based chain extender. , 1998, Journal of biomaterials science. Polymer edition.

[8]  Y. Inoue,et al.  Surface composition and biodegradability of poly(3-hydroxybutyric acid)/poly(vinyl alcohol) blend films , 1998 .

[9]  K. Woodhouse,et al.  Structure‐property relationships of degradable polyurethane elastomers containing an amino acid‐based chain extender , 2000 .

[10]  H. Janik,et al.  Morphology, thermal and mechanical properties of solution-cast polyurethane films , 1990 .

[11]  V. Shilov,et al.  Structural peculiarities of block copolyurethanes with peptide links as rigid block extenders. , 1983, Biomaterials.

[12]  N. Lamba.  Polyurethanes in Biomedical Applications , 1997 .

[13]  Henry Lee,et al.  Handbook of Epoxy Resins , 1967 .

[14]  A. H. Navarchian,et al.  Effects of NCO/OH ratio and catalyst concentration on structure, thermal stability, and crosslink density of poly(urethane-isocyanurate) , 2003 .

[15]  K. Woodhouse,et al.  Elastomeric biodegradable polyurethane blends for soft tissue applications , 2002, Journal of biomaterials science. Polymer edition.

[16]  R. Storey,et al.  Hydrolyzable poly (ester-urethane) networks from L-lysine diisocyanate and D,L-lactide/ε-caprolactone homo- and copolyester triols , 1994 .

[17]  S. Cooper,et al.  Structure‐property relationships in polycaprolactone‐polyurethanes , 1983 .

[18]  K. Woodhouse,et al.  In vitro degradation and erosion of degradable, segmented polyurethanes containing an amino acid-based chain extender , 2001, Journal of biomaterials science. Polymer edition.

[19]  S. Gogolewski,et al.  In vitro degradation of novel medical biodegradable aliphatic polyurethanes based on ϵ-caprolactone and Pluronics® with various hydrophilicities , 2002 .

[20]  J. Smedinga,et al.  Biodegradable lysine diisocyanate-based poly(glycolide-co-epsilon-caprolactone)-urethane network in artificial skin. , 1990, Biomaterials.

[21]  K. Menard.  Dynamic Mechanical Analysis: A Practical Introduction , 1997 .

[22]  M. Okada.  Chemical syntheses of biodegradable polymers , 2002 .

[23]  S. Gogolewski,et al.  Guided tissue regeneration using biodegradable membranes of polylactic acid or polyurethane. , 1992, Journal of clinical periodontology.

[24]  Paul Nieuwenhuis,et al.  Growth of a neo‐artery induced by a biodegradable polymeric vascular prosthesis , 1983 .

[25]  G Galletti,et al.  Long-term patency of regenerated neoaortic wall following the implant of a fully biodegradable polyurethane prosthesis: experimental lipid diet model in pigs. , 1989, Annals of vascular surgery.

[26]  Toshio Hayashi,et al.  BIODEGRADABLE POLYMERS FOR BIOMEDICAL USES , 1994 .

[27]  S. Gogolewski,et al.  Degradable, microporous vascular prosthesis from segmented polyurethane , 1986 .

[28]  A. White,et al.  Cellulose acetate butyrate and poly(hydroxybutyrate-co-valerate) copolymer blends , 1992 .

[29]  T. Hatakeyama,et al.  Synthesis and physical properties of polyurethanes from saccharide-based polycaprolactones , 1998 .

[30]  S. Gogolewski,et al.  Synthesis and characterization of biodegradable poly(?-caprolactone urethane)s. I. Effect of the polyol molecular weight, catalyst, and chain extender on the molecular and physical characteristics , 2002 .

[31]  Y. Doi,et al.  Physical properties and biodegradability of microbial poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) , 1994 .

[32]  S. Gogolewski,et al.  An artificial skin based on biodegradable mixtures of polylactides and polyurethanes for full-thickness skin wound covering , 1983 .

[33]  P. Dubois,et al.  Macromolecular engineering of lactones and lactides. 24. Controlled synthesis of (R,S)-β-butyrolactone-b-ε-caprolactone block copolymers by anionic and coordination polymerization , 1997 .

[34]  J. Seppälä,et al.  Synthesis and Characterization of a Biodegradable Thermoplastic Poly(ester−urethane) Elastomer , 1997 .

[35]  B. Ramsay,et al.  Polymer blends containing poly(3-hydroxyalkanoate)s , 1994 .

[36]  J. Seppälä,et al.  Crosslinked poly(ester anhydride)s based on poly(ε‐caprolactone) and polylactide oligomers , 2003 .