Photopolymerization and shrinkage kinetics of in situ crosslinkable N-vinyl-pyrrolidone/poly(ε-caprolactone fumarate) networks

Journal of Biomedical Materials Research - Part A

Volumn 84, Issue 2, 2008, Pages 545-556

  Sharifi, Shahriar ^a   Mirzadeh, Hamid ^a,b   Imani, Mohammad ^b   Atai, Mohammad ^b   Ziaee, Farshid ^b  

^a AMIRKABIR UNIVERSITY OF TECHNOLOGY   (Iran)

^b IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

Author keywords

Injectable biomaterials; N vinyl pyrollidone; Photocrosslinking; Poly(caprolactone fumarate); Shrinkage strain; Shrinkage strain rate

Indexed keywords

INJECTABLE BIOMATERIALS; N-VINYL PYROLLIDONE; PHOTOCROSSLINKING; POLYCAPROLACTONE FUMARATE; SHRINKAGE STRAIN;

FOURIER TRANSFORM INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PHOTOPOLYMERIZATION; SHRINKAGE;

KETONES;

1 VINYL 2 PYRROLIDINONE; FUMARIC ACID DERIVATIVE; MONOMER; POLYCAPROLACTONE; POLYCAPROLACTONE FUMARATE; POLYMER; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; BIOCOMPATIBILITY; BIODEGRADABILITY; BIODEGRADABLE IMPLANT; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CROSS LINKING; DRUG DELIVERY SYSTEM; FOURIER TRANSFORMATION; GEL PERMEATION CHROMATOGRAPHY; INFRARED SPECTROSCOPY; KINETICS; MEASUREMENT; MOLECULAR WEIGHT; PHOTOCHEMISTRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CARBONATES; CHEMISTRY, PHYSICAL; CROSS-LINKING REAGENTS; CRYSTALLIZATION; FUMARATES; INDICATORS AND REAGENTS; KINETICS; LIGHT; MOLECULAR WEIGHT; PHOTOCHEMISTRY; POLYESTERS; POTASSIUM; POVIDONE; PROTONS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 38049086742     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.31384     Document Type: Article

References (44)

1. Kim HW, Knowles JC, Kim HE. Hydroxyapatite and gelatin composite foams processed via novel freeze-drying and crosslinking for use as temporary hard tissue scaffolds. J Biomed Mater Res A 2005;72:136-145.
2. Guan L, Davies JE. Preparation and characterization of a highly macroporous biodegradable composite tissue engineering scaffold. J Biomed Mater Res A 2004;71:480-484.
3. Widmer MS, Mikos AG. In: Patrick CW, Mikos AG, McIntire LV, editors. Fabrication of Biodegradable Polymer Scaffolds for Tissue Engineering. NewYork: Pergamon; 1998. p 107-120.
4. Chen J, Park K. Synthesis and characterization of super porous hydrogel composites. J Controlled Release 2000;65:73-82.
5. Park A, Wu B, Griffith LG. Integration of surface modification and 3D fabrication techniques to prepare patterned poly(L-lactide) substrates allowing regionally selective cell adhesion. J Biometer Sci Polym Ed 1998;9:89-110.
6. Temenoff JS, Mikos AG. Injectable biodegradable materials for orthopedic tissue engineering. Biomaterials 2000;21:2405-2412.
7. Peter SJ, Yaszemski MJ, Suggs LJ, Payne RG, Langer R, Hayes WC, Unroe MR, Alemany LB, Engel PS, Mikos AG. Characterization of partially saturated poly(propylene fumarate) for orthopedic application. J Biomater Sci Polym Ed 1997;8:893-904.
8. Peter SJ, Suggs LJ, Yaszemski MJ, Engel PS, Mikos AG. Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger. J Biomater Sci Polym Ed 1999;10:363-373.
9. Jo S, Shin H, Shung AK, Fisher JP, Mikos AG. Synthesis and characterization of oligo(poly(ethylene glycol) fumarate) macromer. Macromolecules 2001;34:2839-2844.
10. Suggs LJ, Kao EY, Palombo LL, Krishnan RS, Widmer MS, Mikos AG. Preparation and characterization of polypropylene fumarate-co-ethylene glycol) hydrogels. J Biomater Sci Polym Ed 1998;9:653-666.
11. He S, Yaszemski MJ, Yasko AW, Engel PS, Mikos AG. Injectable biodegradable polymer composites based on poly (propylene fumarate) crosslinked with poly(ethylene glycol)-dimethacrylate. Biomaterials 2000;21:2389-2394.
12. Behravesh E, Jo S, Zygourakis K, Mikos AG. Synthesis of in situ cross-linkable macroporous biodegradable polypropylene fumarate-co-ethylene glycol) hydrogels. Biomacromolecules 2002;3:374-381.
13. Temenoff JS, Park H, Jabbari E, Conway DE, Sheffield TL, Ambrose CG, Mikos AG. Thermally cross-linked oligo(poly (ethylene glycol) fumarate) hydrogels support osteogenic differentiation of encapsulated marrow stromal cells In vitro. Biomacromolecules 2004;5:5-10.
14. Sawhney AS, Pathdak CP, Hubbel JA. Bioerodible hydrogels based on photopolymerized poly(ethylene glycol)-co-poly (alpha hydroxyl acid) diacrylate macromers. Macromolecules 1993;26:581-587.
15. Davis KA, Burdick JA, Anseth KS. Photoinitiated crosslinked degradable copolymer networks for tissue engineering applications. Biomaterials 2003;24:2485-2495.
16. Anseth KS, Burdick JA. New directions in photopolymerizable biomaterials. MRS Bull 2002;27:130-136.
17. Nguyen KT, West JL. Photopolymerizable hydrogels for tissue engineering applications. Biomaterials 2002;23:4307-4314.
18. Baroli B. Photopolymerization of biomaterials: issues and potentialities in drug delivery, tissue engineering, and cell encapsulation applications. J Chem Technol Biotechnol 2006;81:491-499.
19. Anseth KS, Svaldi DC, Laurencin CT, Langer R. In: Scranton AB, Christopher NB, Peiffer RW, editors. Photopolymerization of Novel Degradable Networks for Orthopedic Applications. Washington DC: American Chemical Society; 1997. p 189-202.
20. Fisher JP, Dean D, Mikos AG. Photo-crosslinking characteristics and mechanical properties of diethyl fumarate/poly(propylene fumarate) biomaterials. Biomaterials 2002;23:4325-4332.
21. Kweon H, Yoo MK, Park IK, Kim TH, Lee H, Lee H, Oh J, Akaike T, Cho C. A novel degradable polycaprolactone networks for tissue engineering. Biomaterials 2003;24:801-808.
22. Fisher JP, Timmer MD, Holland TA, Dean D, Engel PS, Mikos AG. Photoinitiated cross-Linking of the biodegradable polyester poly(propylene fumarate). I. Determination of network structure. Biomacromolecules 2003;4:1327-1334.
23. Grijpma DW, Hou O, Feijen J. Preparation of biodegradable networks by photo-crosslinking lactide, e-caprolactone and trimethylene carbonate-based oligomers functionalized with fumaric acid monoethyl ester. Biomaterials 2005;26: 2795-2802.
24. Mizutani M, Matsuda T. Liquid acrylate-endcapped biodegradable poly(ε-caprolactone-co-trimethylene carbonate). 1. Preparation and visible light-induced photocuring characteristics. J Biomed Mater Res 2002;62:387-394.
25. Grubbs RH, Coots RJ, Pine SH. US Pat 4,919,151, 1990.
26. Anseth KS, Newman SM, Bowman CN. Polymeric dental composites: properties and reaction behavior of multi-methacrylate dental restorations, Adv Polym Sci 1995;122:177-217.
27. Hill-West JL, Chowdhury SM, Sawhney AS, Pathak CP, Dunn RC, Hubbell JA. Prevention of postoperative adhesions in the rat by in situ photopolymerization of bioresorbable hydrogel barriers. J Obstet Gynecol 1994;83:59-64.
28. Muggli D, Burkoth AK, Keyser SA, Lee HR, Anseth KS. Reaction behavior of biodegradable, photo-crosslinkable polyanhydrides. Macromolecules 1998;31:4120-4125.
29. Jabbari E, Wang S, Lu L, Gruetzmacher JA, Ameenuddin S, Hefferan TE, Currier BL, Windebank AJ, Yaszemski MJ. Synthesis, material properties, and biocompatibility of a novel self-crosslinkable poly(caprolactone fumarate) as an injectable tissue engineering scaffold. Biomacromolecules 2005;6:2503-2511.
30. Woodward SC, Brewer PS, Moatamed F. The intracellular degradation of polycaprolactone. J Biomed Mater Res 1985;44:437-444.
31. Pitt CG, Gratzei MM, Kimmei GL, Surles J, Schindler A. Aliphatic polyesters. II. The degradation of poly(DL-lactide), polycaprolactone and their copolymer in vivo. Biomaterilas 1981;2:215-220.
32. He S, Timmer MD, Yaszemski MJ, Yasko AW, Engel PS, Mikos AG. Synthesis of biodegradable poly(propylene fumarate) networks with poly(propylene fumarate)-diacrylate macromers as crosslinking agents and characterization of their degradation products. Polymer 2001;42:1251-1260.
33. Frazier DD, Lathi VK, Gerhart TN, Hayes WC. Ex vivo degradation of a poly(propylene glycol-fumarate) biodegradable particulate composite bone cement. J Biomed Mater Res 1997;35:383-389.
34. Gresser JD, Hsu SH, Nagaoka H, Lyons CM, Nieratko DP, Wise DL, Barabino GA, Trantolo DJ. Analysis of a vinyl pyrrolidone/poly(propylene fumarate) resorbable bone cement. J Biomed Mater Res 1995;29:1241-1247.
35. White TJ, Liechty WB, Guymon CA.The influence of N-vinyl pyrrolidone on the photopolymerization kinetics and mechanical properties in copolymerization with acrylates with increasing functionality. 2005 Annual Meeting, Cincinnati, OH, AICHE.
36. Watts DC, Cash J. Kinetic measurements of photo-polymerization contraction in resins and composites. Meas Sci Technol 1991;2:788-794.
37. Silikas N, Kheraif A.Al, Watts DC. Influence of P/L ratio and peroxide/amine concentrations on shrinkage-strain kinetics during setting of PMMA/MMA biomaterial formulations. Biomaterials 2005;26:197-204.
38. W distribution. Macromolecules 1998;31:7187-7194.
39. Brandrup J, Immergut EH, editors. Polymer Handbook, 3rd ed. New York: Wiley; 1989.
40. Watts DC. Reaction kinetics and mechanics in photo-polymerised networks. Dental Mater 2005;21:27-35.
41. Atai M, Watts DC, Atai Z. Shrinkage strain-rates of dental resin-monomer and composite systems. Biomaterials 2005;26:5015-5020.
42. Andrzejewska E. Photopolymerization kinetics of multifunctional monomers. Prog Polym Sci 2001;26:605-665.
43. Jakubiak J, Nie J, Lindén L-Å, Rabek JF. Crosslinking photo-copolymerization of acrylic acid (and N-vinylpyrrolidone) with triethyleneglycol dimethacrylate initiated by camphorquinone/ethyl-4- dimethylaminobenzoate. J Polym Sci Part A: Polym Chem 2000;38:876-886.
44. Sharifi S, Imani M, Mirzadeh H, Atai M, Shirazi F.Synthesis and characterization of photocureable poly(ε-caprolactone fumarate)/N- vinyl pyrollidone networks: Cure kinetics and MTT cytotoxicity evaluation. 20th European Conference on Biomaterials, 2006, Nantes, France.