Preparation of biodegradable networks by photo-crosslinking lactide, epsilon-caprolactone and trimethylene carbonate-based oligomers functionalized with fumaric acid monoethyl ester.
Biodegradable polymer networks were prepared from fumaric acid derivatives of oligomeric esters. Photo-crosslinkable macromers were prepared by reacting star-shaped hydroxyl-group terminated lactide, epsilon-caprolactone and trimethylene carbonate based oligomers and fumaric acid monoethyl ester in the presence of N,N-dicyclohexylcarbodiimide and 4-dimethylamino pyridine at room temperature. The functionalization method is facile and suited for many hydroxyl-terminated oligomers. The reactivity of the fumarate end groups is such that, upon crosslinking by UV radical polymerization, networks with high gel contents (up to 96%) can be obtained without the addition of reactive diluents. The physical properties of the networks can be tuned by adjusting the composition, architecture and molecular weight of the oligomeric precursors. Such networks, built up of non-toxic compounds and designed to release benign degradation products, may find wide application in tissue engineering and other areas of biomedical research.
Grijpma
Dirk W
DW
Faculty of Science and Technology, Department of Polymer Chemistry and Biomaterials, Institute for Biomedical Technology (BMTI), University of Twente, P.O. Box 217, 7500 AE, Enschede, The Netherlands. d.w.grijpma@utwente.nl
Hou
Qingpu
Q
Feijen
Jan
J
D015761:4-Aminopyridine / Q000031:analogs & derivatives* / Q000737:chemistry; D001672:Biocompatible Materials / Q000737:chemistry*; D001673:Biodegradation, Environmental; D002208:Caproates / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000494:pharmacology*; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry*; D005609:Free Radicals; D005650:Fumarates / Q000737:chemistry*; D005898:Glass / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D008027:Light; D046911:Macromolecular Substances / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008855:Microscopy, Electron, Scanning; D008956:Models, Chemical; D011091:Polyesters / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D013696:Temperature; D013718:Tensile Strength; D023822:Tissue Engineering / Q000379:methods; D014466:Ultraviolet Rays
D001672:Biocompatible Materials; D002208:Caproates; D003432:Cross-Linking Reagents; D004146:Dioxanes; D005609:Free Radicals; D005650:Fumarates; D007783:Lactones; D046911:Macromolecular Substances; D011091:Polyesters; D011108:Polymers; C443643:trimethylene carbonate; C033616:poly(lactide); D004024:Dicyclohexylcarbodiimide; C121056:caprolactone; D015761:4-Aminopyridine; C003885:4-dimethylaminopyridine; C061175:ethyl fumarate