Biodegradation of Polydioxanone
Part 9. Miscellaneous Biopolymers and Biodegradation of Polymers
Dr. Haruo Nishida,
Dr. Haruo Nishida
- [email protected]
- +81-948-22-5706 | Fax: +81-948-22-5706
Kinki University, Molecular Engineering Institute, 11-6 Kayanomori, Iizuka, Fukuoka, Japan, 820-8555
Search for more papers by this authorDr. Haruo Nishida,
Dr. Haruo Nishida
- [email protected]
- +81-948-22-5706 | Fax: +81-948-22-5706
Kinki University, Molecular Engineering Institute, 11-6 Kayanomori, Iizuka, Fukuoka, Japan, 820-8555
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Chemical Structure
- Chemical Analysis and Detection
- Functions
- Hydrolyzability
- Depolymerizability
- Physiology
- Biodegradation
- In-vivo Degradation
- Enzymatic Degradation
- Microbial Degradation
- Production
- PDO
- PPDO
- Ring-opening Polymerization
- Enzymatic Polymerization
- Producers, Costs, and World Market
- Applications
- Outlook and Perspectives
- Patents
Polymer/Polymerization
- Akieda, H., Shioya, Y., Kajita, M., Ozu, K. (2001P) Process for producing poly(p-dioxanone), and poly(p-dioxanone) monofilament and process for producing the same. WO 2001019891.
- Baggett, J. M., Horvath, J. W., Wilson, B. W. (1968P) Polymerization of para-dioxanone and derivatives. US Patent 3,391,126.
- Bezwada, R. S., Shalaby, S. W., Newman, H., Jr., Kafrawy, A. (1987) Crystalline copolymers of p-dioxanone and lactide and surgical devices made therefrom. US Patent 4,643,191.
- Bezwada, R. S., Kronenthal, R. L. (1991P) Random copolymers of p-dioxanone, lactide and/or glycolide as coating polymers for surgical filaments. European Patent 0,411,545 A1.
- Cox, E. F., Hostettler, F. (1962Pa-i) Polymerization of cyclic esters. US Patent 3,021,309-17.
- Cox, E. F., Hostettler, F. (1965P) Polymerization of cyclic esters. US Patent 3,190,858.
- Critchfield, F. E., Lundberg, R. D. (1972Pa) Production of relatively high molecular weight polymers of cyclic esters. Canadian Patent 900091.
- Critchfield, F. E., Lundberg, R. D. (1972Pb) Method for the manufacture of relatively high molecular weight polymers of cyclic esters. Canadian Patent 900093.
- Forschner, T. C. (1997P) Method for preparing poly-p-dioxanone polymer. WO 97/21753.
- Forschner, T. C., Gwyn, D. E., Veith, C. A. (1998P) Method for preparing poly-p-dioxanone polymer in the melt. WO 98/08887.
- Nishida, H., Yamashita, M. (2000Pa) Metal-free p-dioxanone polymers, their enzymatic preparation, and medical goods or sanitary products therefrom. Japanese Patent 2000044658 A2.
- Schultz, H. S. (1962Pa) Polymers of 2-p-dioxanone and method for making same. US Patent 3,063,967.
- Schultz, H. S. (1962Pb) Polymers of 2-p-dioxanone. US Patent 3,063,968.
- Shalaby, S. W., Koelmel, D. F. (1984P) Copolymers of p-dioxanone and 2,5-morpholinediones and surgical devices formed therefrom having accelerated absorption characteristics. US Patent 4,441,496.
- Snapp, T. C., Blood, A. E. (1972P) Method of preparing 2-p-dioxanone polymers. US Patent 3,645,941.
- Weipert, E. A. (1962P) Polymerization of 2-p-dioxanone with sulfuric acid. US Patent 3,020,289.
Processing
- Broyer, E (1991P) Thermal treatment of thermoplastic filaments. European Patent 0,415,783 A2.
- Gertzman, A. A., Thompson, D. R. (1983P) Formteile für chirurgische Zwecke und Verfahren zu ihrer Herstellung. DE 3227828 A1.
Alloys/Composites
- Borysko, E. (1984P) Sucrose and/or lactose nucleating agents for the crystallization of polydioxanone. US Patent 4,444,927.
- Brizzolara, N. S., Lanzilotti, M. G., Lawter, J. R. (1990P) Method for the treatment of periodontal disease by sustained delivery of a therapeutic agent to the periodontal pocket, composition of matter therefor and apparatus for the administration thereof. European Patent 0,374,531 A2.
- Doddi, N., Versfelt, C. C., Wasserman, D. (1977Pa) Arzneimittel mit Depotwirkung. DE 2821949 A1.
- Farr, M. P., Lincoln, D. M., Moyers, C. G. (1997P) Stabilized dioxanone polymers. European Patent 0,763,559 A2.
- Koelmel, D. F., Shalaby, S. W., Jamiolkowski, D. D. (1986P) Compatible blends of poly(p-dioxanone) and poly(alkylene phenylene-bis-oxyacetate) and absorbable surgical devices made therefrom. European Patent 0,185,467,A2.
- Nishida, H., Yamashita, M. (1998Pa) Biodegradable poly(p-dioxanone) compositions with improved stability and their moldings. Japanese Patent 10259297 A2.
- Walter, E. R., Koleske, J. V. (1972P) Crystalline polymer alloys comprising a polymer from a cyclic ester and an alkene polymer. US Patent 3,632,687.
Applications
- Bezwada, R. S., Hunter, A. W. (1994P) Castor oil polymers for needle coatings. European Patent 0,610,086 A2.
- Chen, C., Weaver, G., Kindberg, R., Carroll, K., Spengler, R. (1992P) Polymeric endoscopic ligature. European Patent 0,477,020 A1.
- Cooper, K., Chen, C. C., Scopelianos, A. G. (1996P) Hard tissue bone cements and substitutes. European Patent 0,714,666 A1.
- Doddi, N., Versfelt, C. C. (1977Pb) Synthetic absorbable surgical devices of poly-dioxanone. US Patent 4,052,988.
- Dorband, G. C., Liland, A., Menezes, E. V., Steinheuser, P., Popadiuk, N., Failla, S. J. (1986P) Surgical fastening device and method for manufacture. European Patent 0,202,090 A2.
- Dunn, R. L., Tipton, A. J., Southard, G. L., Rogers, J. A. (1991P) Biodegradable system for regenerating the periodontium. WO 91/01126.
- Jamiolkowski, D. D., Newman, H. D., Jr., Datta, A., Tandon, R., Chen, I-J., Suryadevara, J., Canterberry, B. A., Fitzgerald, S. E. (1996P) Medical devices containing high inherent viscosity poly(p-dioxanone). European Patent 0,691,359 A2.
- Lipinsky, E. S., Browning, J. D. (1995P) Degradable polydioxanone-based materials. WO 95/09164.
- Nagashima, M., Yamashita, M., Nishida, H. (2001P) Biodegradable heat-sealable p-dioxanone polymer bags and their manufacture. Japanese Patent 2001018983.
- Nishida, H. (2000Pb) Nonporous moisture-permeable films with excellent biodegradability. Japanese Patent 2000017066 A2.
- Nishida, H., Nagashima, M., Ohura, M. (2001P) Biodegradable p-dioxanone polymer porous film. Japanese Patent 2001002810.
- Potts, E. J. (1983P) Disposable articles coated with degradable water insoluble polymers. US Patent 4,372,311.
- Potts, J. E. (1985P) Disposable articles coated with degradable water insoluble polymers. US Patent 4,503,098.
- Prisell, P., Norstedt, G. (1990P) Pharmaceutical preparation. WO 90/05522.
- Schechtman, L. A. (1991P) Disposable sanitary articles. WO 91/10004; US Patent 5,026,589.
- Suzuki, K., Fukuda, K. (1993P) Minute polymeric rod for preventing tear flow into the lacrimal duct. Japanese Patent 05092015 A2.
- Yamashita, M., Hattori, N., Nishida, H. (1999P) Biodegradable poly(p-dioxanone) compositions and its moldings as hygienic products. Japanese Patent 11005893 A2.
- Yamashita, M., Nishida, H. (2000Pa) Biodegradable heat-shrinkable p-dioxanone polymer films and their manufacture. Japanese Patent 2000301608.
Biodegradation/Recycling
- Nishida, H., Yamashita, M., Hattori, N. (1998Pb) Methods for the preparation of 2-p-dioxanone. Japanese Patent 10045744.
- Nishida, H., Hattori, N., Yamashita, M (1998Pc) Methods for preparation of 2-p-dioxanone by thermolysis. Japanese Patent 10045745.
- Nishida, H., Konno, M. (2000Pc) Treatment of aliphatic polyether-ester polymers. Japanese Patent 2000103843.
Monomer Production
- Forschner, T. C. (1994P) process for preparing para-dioxanones. US Patent 5,310,945.
- Gresham, W. F. (1944P) Preparation of organic esters. US Patent 2,364,438.
- Guest, H. R., Kiff, B. W. (1959P) Process for the production of 2-paradioxanone. US Patent 2,900,395.
- Hattori, N. (1998P) Preparation of 2-p-dioxanone as monomers. Japanese Patent 10120675 A2.
- Mayhew, R. L., Glickman, S. A. (1964P) Preparation of 2-p-dioxanone by dehydrogenating diethylene glycol in the presence of added hydrogen. US Patent 3,119,840.
- McNamee, R. W., Blair, C. M. (1938P) Process for the production of 2-p-dioxanone. US Patent 2,142,033.
- Nakatani, S., Matsumoto, T., Nakahara, Y., Akieda, H., Ishitoku, T. (2001P) Process for the preparation of purified salts of (2-hydroxyethoxy)acetic acid. European Patent 1,138,664 A2.
- Suzuki, S. (1978P) Process for preparing 1,4-dioxan-2-ones. US Patent 4,070,375.
- Souma, Y. (1991P) Process for producing lactones. US Patent 4,990,629.
- Yamashita, M., Nagashima, M., Nishida, H. (2000Pb) Manufacture of 2-p-dioxanones from diethylene glycols. Japanese Patent 2000351775 A2.
References
- Ajioka, M., Enomoto, K., Suzuki, K., Yamaguchi, A. (1995) The basic properties of poly(lactic acid) produced by the direct condensation polymerization of lactic acid, J. Environ. Polym. Degrad. 3, 225–234.
- Bezwada, R. S., Jamiolkowski, D. D., Cooper, K. (1997) Poly(p-dioxanone) and its copolymers, in: Handbook of Biodegradable Polymers ( A. J. Domb, J. Kost, D. M. Wiseman, Eds.), Singapore: Harwood, pp. 29–61.
- Böstman, O. M. (1991) Absorbable implants for the fixation of fractures, J. Bone Joint Surg. 73A, 148–153.
-
Cady, R. B.,
Siegel, J. A.,
Mathien, G.,
Spadaro, J. A.,
Chase, S. E.
(1999)
Physical response to absorbable polydioxanone bone pins in growing rabbits,
J. Biomed. Mater. Res. 48,
211–215.
10.1002/(SICI)1097-4636(1999)48:3<211::AID-JBM2>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- Carothers, W. H., Dorough, G. L., Van Natta, F. J. (1932) Studies of polymerization and ring formation. X. The reversible polymerization of six-membered cyclic esters, J. Am. Chem. Soc. 54, 761–772.
- Feng, X.-D., Jia, Y. (1997) Synthesis and drug controlled release of block copolymers of poly(L-lactide) with poly(D,L-lactide) and related monomers, Macromol. Symp. 118, 625–630.
- Fraunhofer, J. A., Storey, R. S., Stone, I. K., Masterson, B. J. (1985) Tensile strength of suture materials, J. Med. Mater. Res. 19, 595–600.
- Gilbert, R. D., Stannett, V., Pitt, C. G., Schindler, A. (1982) The design of biodegradable polymers: Two approaches, in: Developments in Polymer Degradation-4 ( N. Grassie, Ed.), London: Applied Science Publishers, pp. 259–293.
- Greisler, H. P., Petsikas, D., Lam, T. M., Patel, N., Ellinger, J., Cabusao, E., Tattersall, C. W., Kim, D. U. (1993) Kinetics of cell prolification as a function of vascular graft material, J. Biomed. Mater. Res. 27, 955–961.
- Hall, Jr., H. K., Schneider, A. K. (1958) Polymerization of cyclic esters, urethanes, ureas and imides, J. Am. Chem. Soc. 80, 6409–6412.
- Hollo, E. (1928) Untersuchungen über den Einfluß des Ring-Sauerstoffatoms auf dìe Reaktionsgeschwindigkeit gewisser Lactone, Ber. Deutsch. Chem. Ges. 61B, 895–906.
- Ishaug-Riley, S. L., Okun, L. E., Prado, G., Mark, P., Applegate, M. A., Ratcliffe, A. (1999) Human articular chondrocyte adhesion and proliferation on synthetic biodegradable polymer films, Biomaterials 20, 2245–2256.
- Ishikiriyama, K., Pyda, M., Zhang, G., Forschner, T., Grebowicz, J., Wunderlich, B. (1998) Heat capacity of poly-p-dioxanone, J. Macromol. Sci.-Phys. B37, 27–44.
- Kemper, J. J., Schechtman, L. A. (1994) Synthesis and some properties of poly(p-dioxanone), Third National Meeting of the Bio/Environmentally Degradable Polymer Society, Boston, MA, p. 11.
-
Kricheldorf, H. R.,
Damrau, D.-O.
(1998)
Polylactones, 42 Zn L-lactate-catalyzed polymerizations of 1,4-dioxan-2-one,
Macromol. Chem. Phys. 199,
1089–1097.
10.1002/(SICI)1521-3935(19980601)199:6<1089::AID-MACP1089>3.0.CO;2-S CAS Web of Science® Google Scholar
- Lebedev, B. V., Bykova, T. A., Kiparisova, E. G., Belen'kaya, B. G., Filatova, V. N. (1995) Thermodynamics of p-dioxanone, of its polymerization, and of poly(p-dioxanone) at 0–450 K, Vysokomol. Soedin. Ser. A 37, 187–196.
-
Lee, K.-H.,
Chu, C. C.
(2000)
The role of superoxide ions in the degradation of synthetic absorbable sutures,
J. Biomed. Res. 49,
25–35.
10.1002/(SICI)1097-4636(200001)49:1<25::AID-JBM4>3.0.CO;2-I CAS PubMed Web of Science® Google Scholar
- Lin, H. L., Chu, C. C., Grubb, D. (1993) Hydrolytic degradation and morphologic study of poly-p-dioxanone, J. Biomed. Mater. Res. 27, 153–166.
- Nishida, H., Konno, M., Ikeda, A., Tokiwa, Y. (2000a) Microbial degradation of poly(p-dioxanone) I. Isolation of degrading microorganisms and microbial decomposition in pure culture, Polym. Degrad. Stab. 68, 205–217.
- Nishida, H., Konno, Tokiwa, Y. (2000b) Microbial degradation of poly(p-dioxanone) II. Isolation of hydrolyzates-utilizing microorganisms and utilization of poly(p-dioxanone) by mixed culture, Polym. Degrad. Stab. 68, 271–280.
- Nishida, H., Yamashita, M., Hattori, N., Endo, T., Tokiwa, Y. (2000c) Thermal decomposition of poly(1,4-dioxan-2-one), Polym. Degrad. Stab. 70, 485–496.
- Nishida, H., Yamashita, M., Nagashima, M., Hattori, N., Endo, T., Tokiwa, Y. (2000d) Theoretical prediction of molecular weight on autocatalytic random hydrolysis of aliphatic polyesters, Macromolecules 33, 6595–6601.
- Nishida, H., Yamashita, M., Endo, T., Tokiwa, Y. (2000e) Equilibrium polymerization behavior of 1,4-dioxan-2-one in bulk, Macromolecules 33, 6982–6986.
-
Nishida, H.,
Yamashita, M.,
Nagashima, M.,
Endo, T.,
Tokiwa, Y.
(2000f)
Synthesis of metal-free poly(1,4-dioxan-2-one) by enzyme-catalyzed ring-opening polymerization,
J. Polym. Sci.: Part A: Polym. Chem. 38,
1560–1567.
10.1002/(SICI)1099-0518(20000501)38:9<1560::AID-POLA20>3.0.CO;2-F CAS Web of Science® Google Scholar
- Ray, J. A., Doddi, N., Regula, D., Williams, J. A., Melveger, A. (1981) Polydioxanone (PDS), A novel monofilament synthetic absorbable suture, Surg. Gynecol. Obstet. 153, 497–507.
- Sabino, M. A., Marquez, L., Feijoo, J. L. (1998) Hydrolytic degradation study of polydioxanone and lifetime prediction, Rev. Tec. Ing. Univ. Zulia. 21, 170–178.
- Sabino, M. A., Feijoo, J. L., Müller, A. J. (2000a) Crystallisation and morphology of poly(p-dioxanone), Macromol. Chem. Phys. 201, 2687–2698.
- Sabino, M. A., Gonzalez, S., Marquez, L., Feijoo, J. L. (2000b) Study of the hydrolytic degradation of polydioxanone PPDX, Polym. Degrad. Stab. 69, 209–216.
- Saito, N., Okada, T., Horiuchi, H., Murakami, N., Takahashi, J., Nawata, M., Ota, H., Nozaki, K., Takaoka, K. (2001) A biodegradable polymer as a cytokine delivery system for inducing bone formation, Nature Biotechnol. 19, 332–335.
- Slivka, M. A., Chu, C. C., Zhang, Y. L. (2001) Laser confocal microscopic study of pH profiles of synthetic absorbable fibers upon in vitro hydrolytic degradation, J. Mater. Sci.: Mater. Med. 12, 241–247.
- Song, C. X., Cui, X. M., Schindler, A. (1993) Biodegradable copolymers based on p-dioxanone for medical application, Med. & Biol. Eng. & Comput. 31, S147–S151.
- Törmälä, P. (1992) Bioabsorbable surgical composite materials, Adv. Mater. 4, 589–591.
- Tomihata, K., Suzuki, M., Oka, T., Ikada, Y. (1998) A new resorbable monofilament suture, Polym. Degrad. Stab. 59, 13–18.
- Viñas, F. C., Ferris, D., Kupsky, W. J., Dujovny, M. (1999) Evaluation of expanded polytetrafluoroethylene (ePTFE) versus polydioxanone (PDS) for the repair of dura mater defects, Neurol. Res. 21, 262–268.
- Wang, H., Dong, J. H., Qiu, K. Y., Gu, Z. W. (1998) Synthesis of poly(1,4-dioxan-2-one-co-trimethylene carbonate) for application in drug delivery system, J. Polym. Sci.: Part A: Polym. Chem. 36, 1301–1307.
-
Williams, D. F.
(1981)
Enzymic hydrolysis of polylactic acid,
Eng. Med. 10,
5–7.
10.1243/EMED_JOUR_1981_010_004_02 Google Scholar
- Williams, D. F. (1982) Biodegradation of surgical polymers, J. Mater. Sci. 17, 1233–1246.
- Williams, D. F., Chu, C. C., Dwyer, J. (1984) Effects of enzymes and gamma irradiation on the tensile strength and morphology of poly(p-dioxanone) fibers, J. Appl. Polym. Sci. 29, 1865–1877.
Citing Literature
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: