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Preparation and Modifications of Biodegradable Polyesters for Medical Applications

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Preparation and Modifications of Biodegradable Polyesters for Medical Applications Doctoral Thesis Preparation and modifications of biodegradable polyesters for medical applications Příprava a modifikace biodegradabilních polyesterů pro medicinální aplikace Pavel Kucharczyk September 2013 Zlín, Czech Republic Doctoral study programme: P 2808 Chemistry and Materials Technology 2808V006 Technology of Macromolecular Compounds Supervisor: doc. Ing. Vladimír Sedlařík, Ph.D. Consultant: doc. Ing. Marián Lehocký, Ph.D. CONTENTS CONTENTS .......................................................................................................... 3 ABSTRACT .......................................................................................................... 4 ABSTRAKT .......................................................................................................... 5 LIST OF PAPERS ................................................................................................ 6 THEORETICAL BACKGROUND ...................................................................... 7 1. Introduction to materials for medicine ......................................................................... 7 2. Biodegradable polyesters ........................................................................................... 11 2.1. Polylactic acid (PLA) ..................................................................................... 12 2.2. Polyglycolic acid (PGA) ................................................................................. 13 2.3. Poly(ε-caprolactone) (PCL) ............................................................................ 14 2.4. Polydioxanone (PDO) .................................................................................... 15 2.5. Poly(lactic-co-glycolic acid) (PLGA) ............................................................ 15 3. Chemical synthesis of biodegradable polyesters ........................................................ 16 4. Conducting polycondensation of polyesters .............................................................. 18 5. Modifications to biodegradable polyesters................................................................. 21 5.1. Bulk modifications ......................................................................................... 21 5.2. Surface modifications ..................................................................................... 26 6. Biodegradation of synthetic polyesters under physiological conditions .................... 28 7. Applications of synthetic biodegradable polyesters in medicine ............................. 31 AIMS OF THE DOCTORAL STUDY............................................................... 34 SUMMARY OF THE PAPERS ......................................................................... 35 CONCLUSIONS ................................................................................................. 39 CONTRIBUTIONS TO SCIENCE AND PRACTICE ...................................... 41 ACKNOWLEDGEMENTS ................................................................................ 43 LIST OF SYMBOLS AND ACRONYMS ......................................................... 44 LIST OF FIGURES AND TABLES ................................................................... 45 REFERENCES .................................................................................................... 47 ABSTRACT The work presented here summarizes the very latest advances in the synthesis, modification and degradation of biodegradable polyesters. This body of recognized knowledge was applied to specific polymer systems based on lactic acid – polylactides. Within the experimental part of this work, most attention is paid to polylactide synthesis optimization, involving non-metallic and non- toxic catalyst. Furthermore, chemical modification, through introducing specific groups into the polylactide structure, in addition to chain length prolongation of polymers, by using special postpolycondensation techniques, were undertaken and thoroughly studied in order to meet the relevant requirements for complex polymer applications in medicine. Degradation studies of the polylactides developed under various conditions that simulate the human body provide a comprehensive view on the topic under study. Keywords: biodegradable polymers, synthetic polyesters, synthesis, modification, biodegradation, postpolycondensation, medical application ABSTRAKT Tato doktorská práce poskytuje shrnutí dosavadního stavu poznání v oblasti syntézy, modifikace a degradace biologicky rozložitelných polyesterů. Tento přehled doposud známých poznatků byl aplikován na konkrétní polymerní systémy na bázi polymerů kyseliny mléčné, polylaktidu. Hlavní pozornost v rámci experimentální práce věnována optimalizaci syntézy polylaktidu za použití netoxických nekovových katalyzátorů. Vzhledem k aplikačnímu zaměření této směrem k medicinálním využitím a k požadavkům na fyzikálně chemické vlastnosti polymerních matric je významná pozornost věnována chemické modifikaci připravených polylaktidů ve smyslu zavádění polárních skupin do struktury polymeru a nebo zvyšování délek řetězců pomocí speciálních postpolykondenzačních technik. Pro ucelený přehled je experimentální část doplněna o komplexní studii zaměřující se na charakterizaci hydrolytického rozklady připraveného polylaktidu za specifických podmínek simulující různá prostředí lidského organismu. Klíčová slova: biodegradovatelné polymery, syntetické polyestery, syntéza, modifikace, postpolykondenzace, biodegradace, aplikace v medicíně LIST OF PAPERS Paper I SEDLARIK, V., KUCHARCZYK, P., KASPARKOVA, V., DRBOHLAV, J., SALAKOVA, A., SAHA, P. Optimization of the Reaction Conditions and Characterization of L-Lactic Acid Direct Polycondensation Products Catalyzed by a Non-Metal-Based Compound, J. Appl. Polym. Sci. 2010, vol. 116, no. 3, p. 1597-1602 Paper II KUCHARCZYK, P., POLJANSEK, I., SEDLARIK, V., KASPARKOVA, V., SALAKOVA, A., DRBOHLAV, J., CVELBAR, U., SAHA, P. Functionalization of Polylactic Acid Through Direct Melt Polycondensation in the Presence of Tricarboxylic Acid. J. Appl. Polym. Sci. 2011, vol. 122, p. 1275–1285. Paper III KUCHARCZYK, P., POLJANSEK, I., SEDLARIK, V. The effect of various catalytic systems on solid-state polymerization of poly-(L-lactic acid). J. Macromol. Sci. A. 2012, vol. 49, no. 10, p. 795-805. Paper IV KUCHARCZYK, P., HNATKOVA, E., DVORAK, Z., SEDLARIK, V. Novel aspects of the degradation process of PLA based bulky samples under conditions of high partial pressure of water vapour. Polym. Degrad. Stabil. 2012, vol. 98, no. 1, p. 150-157. THEORETICAL BACKGROUND 1. Introduction to materials for medicine During recent decades great progress has been made in the medical and pharmaceutical field around the world. It is also known that such development has been attributed to discovering and utilizing a new sort of material – biomaterial(s). [1] There are several definitions of biomaterial published in the literature: According to BLACK (1982): “A biomaterial is any pharmacologically inert material, viable or non-viable, natural product or man-made, that is a part of or is capable of interacting in a beneficial way with a living organism” [2, 3]. Later, WILLIAMS (1987) stated, that: “A biomaterial is any non-living material used in medical devices intended to interact with biological systems” [3, 4]. One of the first definitions of biomaterial was determined by the Clemson Advisory Board for Biomaterials and adopted at the sixth Annual International Biomaterials Symposium, 1974 [3, 5]. “A biomaterial is a systemically, pharmacologically inert substance designed for implantation within or for incorporation with a living system”, From a material point of view biomaterials can be divided into 5 groups [6, 7]. Of these, polymeric materials are of special interest due to their unique properties [8, 9, 10]. Biomaterials Ceramics Composites Natural Metals (Aluminum (Metals materials Polymers with ceramic (Steel 316, oxides, calcium (Teflon,PAs, coatings, (Colagen, PMMA,PE, PLA, 316L, Silver, aluminates, materials human tissues, Cobalt, alloys) titanium PEG and others) coated with hyaluronic acid) oxides) carbon) Figure 1 - Basic types of biomaterials Synthetic polymers for medicine On the basis of the definition of biomaterial, it is clear that this should fulfil some specific requirements/features [11, 12]. 1) The material should not cause a sustained inflammatory or undesirable toxic response after implantation into a living organism. 2) The shelf life of a material should be satisfactory. 3) The material should possess appropriate permeability and processability for the intended application. If a material is designed so as to be degradable, then: 4) The mechanical properties of a material should be appropriate for the designated purpose and their variation during degradation should be compatible and predictable with the healing or recovery process. 5) The time of degradation should match the duration of the healing or regeneration process. 6) The degradation products and intermediates should be harmless and able to become metabolized or filtered out from the body. In other words, the material should be bioresorbable (defined in section 2). Similar to other non-polymeric materials, biocompatibility is strictly affected by various factors (material properties), e.g. material chemistry, molecular weight, solubility, the shape and structure of the implant, hydrophilicity/hydrophobicity, lubricity, surface energy, water absorption, degradation and the erosion mechanism [9]. Although there are dozens of
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