Enhancement of bio-compatibility via specific interactions in polyesters modified with a bio-resourceful macromolecular ester containing polyphenol groups

Journal of Biomedical Materials Research - Part A

Volumn 86, Issue 3, 2008, Pages 701-712

  Yen, Kai Cheng ^a   Mandal, Tarun K ^a,b   Woo, E M ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^b DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Miscibility; Polyesters; Polymer blends

Indexed keywords

BUTENES; CRYSTAL GROWTH; ESTERIFICATION; ESTERS; ETHYLENE; FLOW INTERACTIONS; GRAIN BOUNDARIES; INFRARED SPECTROSCOPY; MACROMOLECULES; OPTICAL MICROSCOPY; ORGANIC COMPOUNDS; POLYESTERS; SPECTROSCOPIC ANALYSIS; THERMOANALYSIS;

CAPROLACTONE; FAVORABLE INTERACTIONS; GLASS TRANSITION TEMPERATURE TG; LIGHT OPTICAL MICROSCOPY; MISCIBILITY; MISCIBLE BLENDS; POLY (PBA); POLYETHYLENE ADIPATE; POLYMER BLENDS; POLYPHENOL; SPECIFIC INTERACTIONS; TANNIC ACID; THERMAL ANALYSIS;

GLASS TRANSITION;

ADIPIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ESTER; HYDROXYL GROUP; POLYCAPROLACTONE; POLYESTER; POLYPHENOL; TANNIN;

ARTICLE; BIOCOMPATIBILITY; BIODEGRADABILITY; CHEMICAL INTERACTION; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; GLASS TRANSITION TEMPERATURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; MACROMOLECULE; MICROSCOPY; THERMAL ANALYSIS;

BIOCOMPATIBLE MATERIALS; CALORIMETRY, DIFFERENTIAL SCANNING; ESTERS; FLAVONOIDS; MACROMOLECULAR SUBSTANCES; MATERIALS TESTING; PHENOLS; POLYESTERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TANNINS;

EID: 49149109701     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.31461     Document Type: Article

References (50)

1. Jeong B, Bae YH, Kim SW. In situ gelation of PEG-PLGA-PEG triblock copolymer aqueous solutions and degradation thereof. J Biomed Mater Res 2000;50:171-177.
2. Chenite A, Chaput C, Wang D, Coombes C, Buschmann MD, Hoemann CD, Leroux JC, Atkinson BL, Binette F, Selmani A. Novel injectable neutral solutions of chitosan form biodegradable gels in situ. Biomaterials 2000;21:2155-2161.
3. Sawhney AS, Pathak CP, Van Resburg JJ, Dunn RC, Hubbell JA. Optimization of photopolymerized bioerodible hydrogel properties for adhesion prevention. J Biomed Mater Res 1994;28:831-838.
4. Jeong B, Bae YH, Lee DS, Kim SW. Biodegradable block copolymers as injectable drug-delivery systems. Nature 1997;388:860-862.
5. Park ES, Kim HK, Shim JH, Kim HS, Jang LW, Yoon JS. Compatibility of poly(butadiene-co-acrylonitrile) with poly(L-lactide) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate). J Appl Polym Sci 2004;92:3508-3513.
6. Peter SJ, Miller MJ, Yasko AW, Yaszemski MJ, Mikos AG. Polymer concepts in tissue engineering. J Biomed Mater Res 1998;43:422-427.
7. Lowry KJ, Hamson KR, Bear L, Peng YB, Celaluce R, Evans ML, Anglen OJ, Allen WC. Polycaprolactone/glass bioabsorbable implant in a rabbit humerus fracture model. J Biomed Mater Res 1997;36:536-541.
8. Perez MH, Zinutti C, Lamprecht A, Ubrich N, Astier A, Hoffman M, Bodmeier R, Maincent PH. The preparation and evaluation of poly(ε-caprolactone) microparticles containing both a lipophilic and a hydrophilic drug. J Control Release 2000;65:429-438.
9. Ben-Shabat S, Abuganima E, Raziel A, Domb AJ. Biodegradable polycaprolactone polyanhydrides blends J Polym Sci Part A: Polym Chem 2003;41:3781-3787.
10. Chun YS, Kim WN. Thermal properties of poly(hydroxybutyrate-co-hydroxy valerate) and poly(ε-caprolactone) blends. Polymer 2000;41:2305-2308.
11. Geccoruli G, Pizzoli M, Scandola M. Effect on a low-molecular-weight plasticizer on the thermal and viscoelastic properties of miscible blends ofbacterial poly(3-hydroxybutyrate)-with cellulose acetate butyrate. Macromolecules 1993;26:6722-6726.
12. He Y, Shuai X, Cao AM, Kasuya K, Doi Y, Inoue Y. Enzymatic biodegradation of chemosynthetic atactic P(3HB) enhanced by an amorphous non-biodegradable polymer: Blend of atactic P(3HB) with PMMA. Macromol Rapid Commun 2000;21:1277-1281.
13. Kumagai Y, Doi Y. Enzymatic degradation and morphologies of binary blends of microbial poly(3-hydroxy butyrate) with poly(ε-caprolactone), poly(1,4-butylene adipate and poly(vinyl acetate). Polym Degrad Stab 1992;36:241-248.
14. Tsuji H, Ishizaka T. Porous biodegradable polyesters, 3. Preparation of porous Poly(ε-caprolactone) films from blends by selective enzymatic removal of Poly(L-lactide). Macromol Biosci 2001;1:59-65.
15. Wei M, Shuai XT, Tonelli AE. Melting and crystallization behaviors of biodegradable polymers enzymatically coalesced from their cyclodextrin inclusion complexes. Biomacromolecules 2003;4:783-792.
16. Koenig MF, Huang SJ. Biodegradable blends and composites of polycaprolactone and starch derivatives. Polymer 1995;36:1877-1882.
17. Qiu ZB, Ikehara T, Nishi T. Miscibility and crystallization of poly(ethylene oxide) and poly(ε-caprolactone) blends. Polymer 2003;44:3101-3106.
18. Qiu ZB, Komura M, Ikehara T, Nishi T. Miscibility and crystallization behavior of biodegradable blends of two aliphatic polyesters. Poly(butylene succinate) and Poly(ε-caprolactone). Polymer 2003;44:7749-7756.
19. Mochizuki M, Hirami M. Structural effects on the biodegradation of aliphatic polyesters. Polym Adv Technol 1996;8:203-209.
20. Senda T, He Y, Inoue Y. Biodegradable blends of poly(ε-caprolactone) with α-chitin and chitosan: Specific interactions, thermal properties and crystallization behavior. Polym Int 2001;51:33-39.
21. Honma T, Senda T, Tnoue Y. Thermal properties and crystallization behaviour of blends of poly(ε-caprolactone) with chitin and chitosan. Polym Int 2003;52:1839-1846.
22. Zhu B, Li JC, Yoshie N, Inoue Y. Hydrogen-bonding interaction and crystalline morphology in the binary blends of poly(ε-caprolactone) and polyphenol catechin. Macromol Biosci 2003;3:684-693.
23. Koleske JV, Lundberg RD. Lactone polymers-1, 2. J Polym Sci Polym Phys Ed 1969;7:795-807,897-907.
24. Mandal TK, Woo EM. Miscible blends comprising two carbonyl-containing polymers: Poly(ε-caprolactone) with Poly (benzyl methacrylate). Polym J 1999;31:226-232.
25. Woo EM, Mandal TK. Thermal transition behavior in the miscible polyester/ acrylic polymer pair poly(ε-caprolactone) and poly(phenyl methacrylate). Macromol Rapid Commun 1999;20:46-49.
26. 13C solid state NMR. Polymer 2002;43:1357-1364.
27. Chen HL, Wang SF, Lin TL. Morphological structure of crystalline polymer blend involving hydrogen bonding: Polycaprolactone/Poly(4-vinylphenol) system. Macromolecules 1998;31:8924-8930.
28. Brode GL, Koleske JV. Lactone polymerization and polymer properties. J Macromol Sci Chem 1972;6:1109-1144.
29. Eastmond GC. Poly(ε-caprolactone) blends. Adv Polym Sci 1999;149:59-223.
30. Li JC, He Y, Inoue Y. Thermal and infrared spectroscopic studies on hydrogen-bonding interactions between poly-(ε-caprolactone) and some dihydric phenols. J Polym Sci Part B: Polym Phys 2001;39:2108-2117.
31. He Y, Asakawa N, Inoue Y. Studies on poly(ε-caprolactone)/ thiodiphenol blends: The specific interaction and the thermal and dynamic mechanical properties. J Polym Sci Part B: Polym Phys 2000;38:1848-1859.
32. Kuo SW, Huang CF, Tung YC, Chang FC. Effect of bisphenol A on the miscibility, phase morphology, and specific interaction in immiscible biodegradable poly(ε-caprolactone)/poly(L-lactide) blends. J Appl Polym Sci 2006;100:1146-1161.
33. Haslam E. Natural polyphenols (vegetable tannins) as drugs: Possible modes of action. J Nat Prod 1996;59:205-215.
34. Edelmann A, Lendl B. Toward the optical tongue: Flow-through sensing of tannin-protein interactions based on FTIR spectroscopy. J Am Chem Soc 2002;124:14741-14747.
35. Frazier RA, Papadopoulou A, Mueller-Harvey I, Kissoon D, Green RJ. Probing protein-tannin interactions by isothermal titration microcalorimetry. J Agric Food Chem 2003;51:5189-5195.
36. Baxter NJ, Lilley TH, Haslam E, Williamson MP. Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemistry 1997;36:5566-5577.
37. Chibowski E, Espinosa-Jimenez M, Ontiveros-Ortega A, Gimenez-Martin E. Surface free energy, adsorption and zeta potential in leacril/tannic acid system. Langmuir 1998;14:5237-5244.
38. Zhang SH, Painter PC, Runt J. Dynamics of polymer blends with intermolecular hydrogen bonding: Broad-band dielectric study of blends of Poly(4-vinyl phenol) with Poly(vinyl acetate) and EVA70. Macromolecules 2002;35:8478-8487.
39. Shutava T, Prouty M, Kommireddy D, Lvov Y. pH Responsive decomposable layer-by-layer nanofilms and capsules on the basis of tannic acid. Macromolecules 2005;38:2850-2858.
40. Zhu B, He Y, Yoshie N, Asakawa N, Inoue Y. Partial phase segregation in strongly hydrogen-bonded and miscible blends. Macromolecules 2004;37:3257-3266.
41. Kuo SW, Chan SC, Chang FC. Miscibility enhancement on the immiscible binary blend of poly(vinyl acetate) and poly (vinyl pyrrolidone) with bisphenol A. Polymer 200243:3653-3660.
42. Kwei TK. Effect of hydrogen bonding on the glass transition temperatures of polymer mixtures. J Polym Sci Polym Lett Ed 1984;22:307-313.
43. Maldonado-Santoyo M, Ortiz-Estrada C, Luna-Barcenas G, Sanchez IC, Cesteros LC, Katime I, Nuno-Donlucas SM. Miscibility behavior and hydrogen bonding in blends of poly (vinyl phenyl ketone hydrogenated) and poly(2-ethyl-2-oxazoline). J Polym Sci Part B: Polym Phys 2004;42:636-645.
44. Kwei TK, Pearce EM, Pennacchia JR, Charton M. Correlation between the glass transition temperatures of polymer mixtures and intermolecular force parameters. Macromolecules 1987;20:1174-1176.
45. Chang LL, Woo EM. Thermal, morphology, and NMR characterizations on phase behavior and miscibility in blends of isotactic polystyrene with poly(cyclohexyl methacrylate). J Polym Sci Part B: Polym Phys 2003;41:772-784.
46. Mandal TK, Kuo JF, Woo EM. Miscibility and spherulite growth kinetics in the poly(ethylene oxide)/poly(benzyl methacrylate) system. J Polym Sci Part B: Polym Phys 2000;38:562-572.
47. g-composition dependence. Polymer 2000;41:6663-6670.
48. Meaurio E, Zuza E, Sarasua JR. Miscibility and specific interactions in blends of Poly(L-Lactide) with Poly(vinylphenol). Macromolecules 2005;38:1207-1215.
49. Moskala EJ, Varnell DF, Coleman MM. Concerning the miscibility of poly(vinyl phenol) blends - Ftir study. Polymer 1985;26:228-235.
50. Woo EM, Chiang CP. Glass transition behavior and miscibility in blends of poly(vinyl p-phenol) with two homologous aliphatic polyesters. Polymer 2004;45:8415-8424.