Preparation, Characterization and Antimicrobial Activity of Poly(3-hydroxybutyrate-co-3-hydroxyvalerate)-g-Poly(N-vinylpyrrolidone) Copolymers

Polymer - Plastics Technology and Engineering

Volumn 51, Issue 11, 2012, Pages 1113-1121

  Saad, Gamal R ^a   Elsawy, Moataz A ^b   Elsabee, Maher Z ^a  

^a CAIRO UNIVERSITY   (Egypt)

^b EGYPTIAN PETROLEUM RESEARCH INSTITUTE   (Egypt)

Author keywords

Antimicrobial activity; Biodegradability; Graft copolymers; N vinylpyrrolidone; Poly(3 hydroxybutyrate co 3 hydroxyvalerate); Swelling; Thermal analysis

Indexed keywords

ACTIVE SOILS; ANTI-BACTERIAL ACTIVITY; ANTI-MICROBIAL ACTIVITY; COLD CRYSTALLIZATION TEMPERATURE; FTIR; GLASS STATE; GRAFT POLYMERIZATION; N VINYLPYRROLIDONE; POLY(3-HYDROXYBUTYRATE-CO-3-HYDROXYVALERATE);

BIODEGRADABILITY; BIODEGRADATION; GRAFT COPOLYMERS; SWELLING; THERMOANALYSIS;

GRAFTING (CHEMICAL);

EID: 84864579545     PISSN: 03602559     EISSN: 15256111     Source Type: Journal    
DOI: 10.1080/03602559.2012.680568     Document Type: Article

References (59)

1. Chen, G.Q.; Page, W.J. Production of poly-β-hydroxybutyrate by Azotobacter vinelandii in a two-stage fermentation process. Biotechnol. Techn. 1997, 11, 347-350.
2. Chen, G.Q.; Wu, Q.; Xi, J.Z.; Yu, H.P.; Chan, A. Microbial production of biopolyesters-polyhydroxyalkanoates. Prog. Nat. Sci. 2000, 10, 843-850.
3. Freier, T.; Kunze, C.; Nischan, C.; Kramer, S.; Sternberg, K.; Sas, M.; Hopt, U.T.; Schmitz, K.P. In vitro and in vivo degradation studies for development of a biodegradable patch based on poly(3-hydroxybutyrate). Biomaterials 2002, 23, 2649-2657.
4. Chen, G.Q.; Wu, Q. The application of polyhydroxyalkanoates as tissue engineering materials. Biomaterials. 2005, 26, 6565-6578.
5. Valappil, S.P.; Misra, S.K.; Boccaccini, A.R.; Roy, I. Biomedical applications of polyhydroxyalkanoates, an overview of animal testing and in vivo responses. Expert Rev. Med. Dev. 2006, 3, 853-868.
6. Yu, H.; Meifang, Z.; Zhang, Y.; Chen, Y. Mechanism of the Formation of Concentric Ring-like Patterns on PHBV Spherulites. Polymer Plast. Techn. Eng. 2004, 43, 1-15.
7. Lee, S.N.; Lee, M.Y.; Park, W.P. Thermal stabilization of poly(3-hydroxybutyrate) by poly(glycidyl methacrylate). J. Appl. Polym. Sci. 2002, 83, 2945-2952.
8. Doi, Y. Microbial Polyester, VCH Publishers: New York, 1991, chapter 1.
9. Zhang, L.; Xiong, C.; Deng, X. Miscibility, crystallization and morphology of poly(b-hydroxybutyrate)/poly(D,L-lactide). Polymer 1996, 37, 235-241.
10. Ol'Khov, A.A.; Iordanskii, A.L.; Zaikov, G.E.; Shibryaeva, L.S.; Litvinov, I.A.; Vlasov, S.V. Morphology special features of poly(3-hydroxybutyrate)/low density polyethylene blends. Polym. Plast. Techn. Eng. 2000, 39, 783-792.
11. Koyama, N.; Doi, Y. Miscibility of binary blends of poly[(R)-3-hydroxybutyric acid] and poly[(S)-lactic acid]. Polymer 1997, 38, 1589-1593.
12. Scandola, M.; Focarete, M.L.; Adamus, G.; Sikorska, W.; Baranowska, I.; Swierczek, S.; Gnatowski, M.; Kowalczuk, M.; Jedlinski, Z.Polymer blends of natural poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and a synthetic atactic poly(3-hydroxybutyrate). Character. Biodegrad. Stud. Macromol.1997, 30, 2568-2574.
13. Singh, B.; Bhalla, T.C.; Sharma, N. Induction of biodegradability in the plastic waste through graft copolymerization. Polym. Plast. Techn. Eng. 2009, 48, 1324-1332.
14. Khan, M.A.; Alam, R.; Rahman, A.; Noor, F.G.; Khan, R.A. Physico-mechanical and degradation properties of urea-modified chitosan film photocured with 1-vinyl-2 pyrrolidone. Polym. Plast. Techn. Eng. 2009, 48, 1206-1215.
15. Yoon, J.S.; Lee, W.S.; Jin, H.J.; Chin, I.N. Toughening of poly(3-hydroxybutyrate) with poly(cis-1,4-isoprene). Eur Polym J. 1999, 35, 781-788.
16. Iordanskii, A.L.; Dmitriev, E.V.; Kamaev, P.P.; Zaikov, G.E. Desorption of human serum albumin and human fibrinogen from the poly(3-hydroxybutyrate) surface. Inter. J. Polym. Mater. 2000, 46, 629-639.
17. Ha, C.S.; Cho, W.J. Miscibility, properties, and biodegradability of microbial polyester containing blends. Prog. Polym. Sci. 2002, 27, 759-809.
18. Saad, G.R. Blends of bacterial poly[(R)-3-hydroxybutyrate] with oligo[(R,S)-3-hydroxybutyrate]-diol. Polym. Int. 2002, 51, 338-348.
19. Huang, H.; Hu, Y.; Zhang, J.; Zhang, S.H.; Noda, I.H., Ozaki, Y. Miscibility and hydrogen-bonding interaction in biodegradable polymer blends of poly(3-hydroxybutyrate) and a partially hydrolyzed poly(vinil alcohol). J. Phys. Chem. 2005, 109, 19175-19183.
20. Innocentini-Mei, L.H.; Bartoli, J.R.; Rodrigo, C.B. Mechanical and thermal properties of poly(3-Hydroxybutyrate) blend with starch and starch derivates. Macromol. Symp. 2003, 197, 77-87.
21. Godbole, S.; Gote, S.; Latkar, M.; Chakrabarti, T. Preparation and characterization of biodegradable poly-3-hydroxybutyrate-starch blend films. Bioresour. Techn. 2003, 86, 33-37.
22. Fernandes, E.G.; Pietrini, M.; Chiellini, E. Thermo-mechanical and morphological characterization of plasticized poly[(R)-3-hydroxybutyric acid]. Macromol. Symp. 2004, 218, 157-164.
23. Reeve, R.S.; McCarthy, S.; Gross, R.A. Preparation and characterization of (R)-poly(3-hydroxybutyrate)-poly(ε-capro1actone) and (r)-poly(3-hydroxybutyrate)-poly(1actide) degradable diblock copolymers. Macromolecules 1993, 26, 888-894.
24. Lotti, N.; Pizzoli, M.; Ceccorulli, G.; Scandola, M. Binary blends of microbial poly(3-hydroxybutyrate) with polymethacrylates. Polymer 1993, 34, 4935-4940.
25. Yalpani, M.; Marchessault, R.H.; Moin, F.G.; Monaseterios, C.J. Synthesis of poly(3-hydroxyalkanoate) (PHA) conjugates: PHA-carbohydrate and PHA-synthetic polymer conjugates. Macromol. 1991, 24, 6046-6049.
26. Hirt, T.D.; Neuensch, W.P.; Suter, U.W. Synthesis of degradable, biocompatible, and tough block-copolyesterurethanes. Macromol. Chem. Phys. 1996, 197, 4253-4268.
27. Lendlein, A.; Neuensch, W.P.; Suter, U.W. Tissue-compatible multiblock copolymers for medical applications, controllable in degradation rate and mechanical properties. Macromol. Chem. Phys. 1998, 199, 2785-2796.
28. Saad, G.R.; Lee, Y.J.; Seliger, H. Synthesis and characterization of biodegradable poly(ester-urethanes) based on bacterial poly(R-3-hydroxybutyrate). J. Appl. Polym. Sci. 2002, 83, 703-18.
29. Andrade, A.P.; Neuenschwander, P.; Hany, R.; Egli, T.; Witholt, B.; Li, Z. Synthesis and characterization of novel copoly(ester-urethane) containing blocks of poly-[(r)-3-hydroxyoctanoate] and poly-[(r)-3-hydroxybutyrate] (2). Macromol. 2003, 5, 4946-4950.
30. Zhao, Q.; Cheng, G.X. Preparation of biodegradable poly(3-hydroxybutyrate) and poly(ethylene glycol) multiblock copolymers. J. Mater. Sci. 2004, 39, 3829-3831.
31. Li, J.; Li, X.; Ni, X.; Leong, K.W. Synthesis and Characterization of New Biodegradable Amphiphilic Poly(ethylene oxide)-b-poly[(R)-3-hydroxy butyrate]-b-poly(ethylene oxide) Triblock Copolymers. Macromol. 2003, 36, 2661-2667.
32. Zhao, Q.; Cheng, G.X.; Li, H.M.; Ma, X.L.; Zhang, L.G. Synthesis and characterization of biodegradable poly(3-hydroxybutyrate) and poly(ethylene glycol) multiblock copolymers. Polymer 2005, 46, 10561-10567.
33. Bahari, K.; Mitomo, H.; Enjoji, T.; Hasegawa, S.; Yoshii, F.; Makuuchi, K. Radiation-induced graft polymerization of styrene onto poly(3-hydroxybutyrate) and its copolymer with 3-hydroxyvalerate. Angew. Makromol. Chem. 1997, 250, 31-44.
34. Mitomo, H.; Enjoji, T.; Watanabe, Y.; Yoshii, F.; Makuuchi, K. Radiation induced graft polymerization of poly (3-hydroxybutyrate) and its copolymer. Pure Appl. Chem. 1995, A32 (3), 429-442.
35. Mitomo, H.; Yoshii, F.; Makuuchi, K.; Saito, T. Int. Symp. Biodeg. Polym. 1995, 73.
36. Lee, H.S.; Lee, T.Y. Graft polymerization of acrylamide onto poly(hydroxybutyrate-co-hydroxyvalerate) films. Polymer 1997, 38, 4505-4511.
37. Chen, C.; Peng, S.; Fei, B.; Zhuang, Y.; Dong, L.; Feng, Z.; Chen, S.; Xia, Z. Synthesis and characterization of maleated poly(3-hydroxybutyrate). J. Appl. Polym. Sci. 2003, 88, 659-668.
38. Wang, W.; Zhang, Y.; Chen, Y. Graft Copolymerization of N-vinylpyrrolidone onto poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in homogeneous solution. Iran. Polym. J. 2007, 16, 195-205.
39. Lao, H.; Renard, E.; Langlois, V.; Valleé-Rehel, K.; Linossier I. Surface functionalization of PHBV by HEMA grafting via UV treatment: Comparison with thermal free radical polymerization. J. Appl. Polym. Sci. 2010, 116, 288-297.
40. Källrot, M.; Edlund, U.; Albertsson, A.C. Surface functionalization of degradable polymers by covalent grafting. Biomaterials 2006, 27, 1788-1796.
41. Moulinex, J.P. Polyvinylpyrrolidone, In: Water-Soluble Synthetic Polymers: Properties and Behaviour, CRC: Boca Raton, FL, 1984.
42. Haaf, F.; Sanner, A.; Straub, F. Polymers of N-vinylpyrrolidone: Synthesis, characterization and uses. Polym. J. 1985, 17, 143-152.
43. Brunius, C.F.; Edlund, U.; Albertsson, A.C. Synthesis and in vitro degradation of poly(N-vinyl-2-pyrrolidone)-based graft copolymers for biomedical applications. J. Polym. Sci. A Polym. Chem. 2002, 40, 3652-3661.
44. Raghunath, K.; Panduranga, R.K.; Nagarajan, B.; Tomas, J.K. Grafting of poly(vinyl pyrrolidone) onto gelatin and its application as synthetic plasma expander. Eur. Polym. J. 1985, 21, 195-199.
45. Khan, M.A.; Alam, R.; Rahman, A.; Noor, F.G.; Khan, R.A. Physico-Mechanical and Degradation Properties of Urea-Modified Chitosan Film Photocured with 1-Vinyl-2 Pyrrolidone. Polym. Plast. Techn. Eng. 2009, 48, 1206-1215.
46. Nair, M.G.; Mishra, S.K.; Putnam, A.R. Antifungal anthracycline antibiotics, spartanamicins A and B from Micromonospora spp. J. Antibiot. 1992, 45, 1738-1745.
47. Barham, P.; Keller, A.J.; Otun, E.L.; Holmes, P.A. Crystallization and morphology of a bacterial thermoplastic: poly-3-hydroxybutyrate. J. Mater. Sci. 1984, 19, 2781-2794.
48. Organ, S.J. Variation in melting point with molecular weight for hydroxybutyrate/hydroxyvalerate copolymers. Polymer 1993, 34, 2175-2179.
49. Grassie, N.; Murray, E.J.; Holmes, P.A. The thermal degradation of poly(-(D)-β-hydroxybutyric acid): Part 1-Identification and quantitative analysis of products. Polym. Degrad. Stab. 1984, 6, 47-61.
50. Grassie, N.; Murray, E.J.; Holmes, P.A. The thermal degradation of poly(-(D)-β-hydroxybutyric acid): Part 2-Changes in molecular weight. Polym. Degrad. Stab. 1984, 6, 95-103.
51. Skrbic, Z.; Divjakovic, V.Temperature influence on changes of parameters of the unit cell of biopolymer PHB. Polym.1996, 37, 505-507.
52. Bluhm, T.L.; Hamer, G.K. Studies of composition and crystallinity of bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate). Macromolecules 1986, 19, 2865-2871.
53. Jones, R.P.; Greenfield, P.E. A review of yeast ionic nutrition. Part 1: growth and fermentation requriments. Proc. Biochem. 1984, 19, 48-60.
54. Jon, O.M.; Imada, Y.; Muruyama, T. Microbiology 1987, 51, 183-186.
55. Mergaert, J.; Webb, A.; Anderson, C.; Wouters, A.; Swings, J. Microbial degradation of poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in soils. Appl. Environ. Microbiol. 1993, 59, 3233-3238.
56. Kimura, M.; Toyota, K.; Iwatduki, M.; Sawada, H. Effects of soil conditions on biodegradation of plastics and responsible microorganisms. In Doi, Y. and Fukuda, K., eds., Biodegradable Plastics and Polymers, Elsevier Science: London, 1994 pp. 92-106.
57. Jendrossek, D.; Schirmer, A.; Schlegel, H.G. Biodegradation of polyhydroxyalkanoic acids. Appl. Microbiol. Biotechnol. 1996, 46, 451-463.
58. Molitoris, H.P.; Moss, S.T.; deKoning, G.J.M.; Jendrossek, D. Scanning electron microscopy of polyhydroxyalkanoate degradation by bacteria. Appl. Microbiol. Biol. 1996, 46, 570-579.
59. Tsuji, H.; Suzuyoshi, K. Environmental degradation of biodegradable polyesters 1. Poly(ε-caprolactone), poly[(R)-3-hydroxybutyrate], and poly(L-lactide) films in controlled static seawater. Polym. Degrad. Stab 2002, 75, 347-355.