DOCSLIB.ORG

Poly(P-Dioxanone) (PPDO), and Its Copolymers

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Poly(P-Dioxanone) (PPDO), and Its Copolymers http://www.paper.edu.cn MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016 ©2002 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc. JOURNAL OF MACROMOLECULAR SCIENCE Part C—Polymer Reviews Vol. C42, No. 3, pp. 373–398, 2002 POLY( p-DIOXANONE) AND ITS COPOLYMERS Ke-Ke Yang, Xiu-Li Wang, and Yu-Zhong Wang* Center for Degradable and Flame-Retardant Polymeric Materials, School of Chemistry, Sichuan University, Chengdu 610064, P. R. China CONTENTS 1. Introduction ............................................................ 374 2. Synthesis of PDO ....................................................... 374 2.1. Physical Properties of PDO ........................................374 2.2. Synthesis of PDO ..................................................375 3. Ring-Opening Polymerization of PDO . ................................ 376 3.1. Catalyst............................................................376 3.2. Copolymerization Based on PDO ..................................381 4. Properties of PPDO ..................................................... 383 4.1. Solubility ..........................................................384 4.2. Biodegradability ...................................................384 4.3. Thermal Properties.................................................386 4.4. Crystallization and Morphology ....................................386 4.5. Mechanical Properties. ...........................................390 5. Application of PPDO ................................................... 390 5.1. Surgical Suture.....................................................390 5.2. Bone and Tissue Fixation Device ...................................391 5.3. Drug Delivery System. ...........................................391 *Corresponding author. Fax: þ86-28-5412907; E-mail: [email protected] 373 DOI: 10.1081/MC-120006453 1532-1797 (Print); 1532-9038 (Online) Copyright # 2002 by Marcel Dekker, Inc. www.dekker.com 中国科技论文在线 http://www.paper.edu.cn MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016 ©2002 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc. 374 YANG, WANG, AND WANG 6. Conclusion .............................................................. 391 References .............................................................. 392 ABSTRACT This paper reviews the synthesis, properties, and applications of bio- degradable polymer, poly(p-dioxanone) (PPDO), and its copolymers. Recent progress in ring-opening polymerization of p-dioxanone employ- ing several effective catalysts is described. Properties of PPDO are given. The copolymers based on PPDO are also discussed. Key Words: Poly(p-dioxanone); Copolymers; Ring-opening polymeri- zation; Biodegradable 1. INTRODUCTION Aliphatic polyesters, with outstanding biodegradability, bioabsorb- ability, and biocompatibility, have attracted great interest from researchers in recent decades. The related papers and patents increased sharply in a very short period, and remarkable progress has been achieved in this field.[1–9] As a result, a series of polyesters and copolyesters have been synthesized success- fully from the lactone monomers including glycolide (GA),[10] lactide (LA),[3,7–9] e-caprolactone (CL),[2,11,12] p-dioxanone (PDO),[4,5,13,14] 1,5-diox- epan-2-one (DXO),[15] 1,3-dioxan-2-one (TMC),[16–18] and so on. Most of them have been applied to make biodegradable products, especially surgical devices such as surgical suture, anchors, staples, tacks, clips, plates, screws, and bone fixation devices.[7,8,14] Compared with other aliphatic polyesters, poly( p-dioxanone) (PPDO) has its own special characteristics. Except for its ultimate biodegradability due to the existence of ester bonds in polymer chains, the unique ether bonds endow it with good flexibility.[19] It has also received the approval of the Food and Drug Administration (FDA) to be used as suture material in gynecology.[19,20] However, PPDO did not become the focus of polyesters for quite a long period. There are two main reasons for this. One reason is that the monomer PDO was not commercially available in the past. The other reason is that the activity of the PDO monomer is comparatively low, and most catalysts that have been mentioned in the available infor- mation are not effective enough to produce the polymer at reasonable cost. Fortunately, the synthetic method of producing PDO has been sim- plified greatly, and studies on PPDO have made rapid development in recent years. 中国科技论文在线 http://www.paper.edu.cn MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016 ©2002 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc. POLY( p-DIOXANONE) AND ITS COPOLYMERS 375 This article presents a review of the synthesis, properties, and applica- tions of PPDO and its copolymers. 2. SYNTHESIS OF PDO 2.1. Physical Properties of PDO p-Dioxanone or 1,4-dioxan-2-one, abbreviated as PDO, is a colorless crystal or liquid. Its molecular weight is 102, and melt point is 24C.[21] Boiling points are 220C, 213–214C, 109–110C, and 92–93C, respectively, under different pressures [760 mmHg (calculated value), 747 mmHg, 22 mmHg, and 10 mmHg].[13,22] There are many ways to characterize its molecular structure, such as nuclear magnetic resonance (NMR) spectroscopy (1H-NMR spectrum), infrared (IR) spectroscopy, and mass spectrometry (MS).[22] The NMR spectrum of PDO exhibits a sharp singlet at d4.40 and two multiplets of equal intensity centered at d3.9 and 4.5. The IR spectrum shows the following absorptions: CH stretching at À1 À1 2900 cm ,C¼O stretching at 1740 cm ,CH2 bending at 1455 and 1432 cmÀ1, CO stretching at 1200, 1130, and 1053 cmÀ1, and other weaker bands at 876, 853, 726 cmÀ1. The mass spectrum of PDO, including parent, Pþ1, and major peaks, appear at 103, 102, 101, 87, 86, 75, 73, 58, 57, 45, 44, 43, 42, 32 m/e, respectively.[22] 2.2. Synthesis of PDO In the early 1970s, Doddi et al.[14] had used ethylene glycol, metallic sodium, and chloroacetic acid to synthesize PDO (Scheme 1). However, the procedure was so complex and the yield so low that it caused a high cost of PDO and seriously hampered the application of PPDO. So this method was substituted in the last decade by a simple method that prepared PDO by oxidative dehydrogenation of diethylene glycol over Cu(O) catalyst supported on silica particles (Scheme 2).[23] Because the resource, diethylene glycol, was very cheap, this one-step reaction sharply decreased the cost of PDO. Purification of PDO is also an important step in order to achieve high molecular weight PPDO. Distillation and recrystallization are both effective ways to purify the monomer. Distillation is usually conducted under high vacuum, considering the rather high boiling point of PDO at normal pressure. Commonly, ethylacetate has been chosen as the recrystallizing solvent. However, the yield of recrystallization is lower than that of distillation. Jiang[24] supplied a method to gain excellent purified PDO by double recrystallization using ethylacetate as solvent with a yield of 30%. 中国科技论文在线 http://www.paper.edu.cn MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016 ©2002 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc. 376 YANG, WANG, AND WANG HOCH2CH2OH + Na HOCH2CH2ONa + H2 + HOCH2CH2OH 1/2ClCH2COOH HOCH2CH2OCH2OONa + NaCl + HOCH2CH2OH distillation HOCH2CH2OCH2COONa + NaCl HOCH2CH2OH washing by acetone HOCH CH OCH COONa 2 2 2 CH3COCH3 + NaCl + - H3O + Cl HOCH2CH2OCH2COOH + H2O + NaCl precipitation with ethanol and filtration HOCH2CH2OCH2COOH ++ H2O C2H5OH NaCl + C2H5OH distillation HOCH2CH2OCH2COOH H2O + C2H5OH O O O Scheme 2. O Catalyst O HOCH2CH2OCH2CH2OH O Scheme 1. 3. RING-OPENING POLYMERIZATION OF PDO 3.1. Catalyst The polyester PPDO is synthesized by ring-opening polymerization from the monomer PDO. In this polymerization process, the catalyst plays an important role, which influences not only the polymeric parameters such as reaction rate, conversion, and yield, but also the properties of the polymer such as molecular weight and polydispersity. Several catalysts, especially organometallics, have been found effective to initiate the ring-opening polymerization of lactone, even if some of them have not been reported to apply to PDO. Most catalysts are the derivatives of organometallics of heavy metals such as Ti, Zr, Sn, Cd, Al, Zn, Y, La, and Yb. Thereafter, the catalysts that have been used frequently will be listed in detail. 中国科技论文在线 http://www.paper.edu.cn MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016 ©2002 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc. POLY( p-DIOXANONE) AND ITS COPOLYMERS 377 3.1.1. Organic Tin Compounds Organic tin compounds, including stannous octoate,[25–29] stannous oxalate,[30] dibutyltin oxide,[31] stannic bromide, stannic chloride, stannous bromide, stannous chloride,[32–34] stannous acetylacetonate,[35] and [16] Bu2SnOct2, have been used most frequently in ring-opening polymeriza- tion of lactone. Among these, stannous octoate (SnOct2) has been found the most effective catalyst. Moreover,
Load more

Recommended publications
  • Absorbable Polymers
    Elastomeric Foams Films and Coatings Absorbable Sutures, Staples, Pledgets and Clips Polymers Tissue Engineering Orthopedic Fixation Devices Controlled Drug Delivery Wound Healing and Adhesion Prevention Bezwada Biomedical LLC 15-1 Ilene Court Hillsborough, NJ 08844 Tel: 908-281-7529, Email: [email protected] 1 Introduction to Absorbable Polymers Polymers that are designed to degrade under physiological conditions are referred to as absorbable polymers. These polymers are sometimes also referred to as biodegradable or bioerodible or bioabsorbable polymers. Bezwada Biomedical is pleased to offer a range of absorbable polymers for technical evaluation and product development. These absorbable polymers and copolymers can be used in various biomedical applications including: • Encapsulation and Controlled drug delivery • Gene Therapy • Dental and Medical Devices • Sutures, Staples, Clips and meshes • Orthopedic fixation devices • Tissue engineering scaffolds • Elastomeric films and medical device coatings Most of the synthetic absorbable polyesters are produced by ring opening homopolymerization or copolymerization of five key lactone based safe and biocompatible monomers. These are glycolide, L-lactide and its isomers, -caprolactone, p-dioxanone and trimethylene carbonate (TMC). The structures and IUPAC names of these monomers and corresponding polymers are shown below in Figure 1 and Figure 2 respectively. O O O O O O O O O O O Glycolide L (-) Lactide p-dioxanone (1,4-dioxane-2,5-dione) (3,6-dimethyl-1,4-dioxane-2,5-dione) (1,4-dioxane-2-one)
    [Show full text]
  • Tuning the Mechanical Properties and Degradation Properties of Polydioxanone Isothermal Annealing
    Turkish Journal of Chemistry Turk J Chem (2020) 44: 1430-1444 http://journals.tubitak.gov.tr/chem/ © TÜBİTAK Research Article doi:10.3906/kim-2006-55 Tuning the mechanical properties and degradation properties of polydioxanone isothermal annealing 1,2 1,2 1 1,2 1,2 1,2 1, Xiliang LIU , Shaomin FENG , Xin WANG , Jin QI , Dong LEI , Yadong LI , Wei BAI * 1 Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, P.R. China 2 University of Chinese Academy of Sciences, Beijing, P.R. China Received: 22.06.2020 Accepted/Published Online: 11.08.2020 Final Version: 26.10.2020 Abstract: Polydioxanone (PPDO) is synthesized by ring-opening polymerization of p-dioxanone, using stannous octoate as the catalyst. The polarized optical micrograph (POM) shows thes pherulite growth rate of PPDO decreases with an increase in the isothermal crystallization temperature. PPDO is compression-molded into bars, and PPDO bars are subjected to isothermal annealing at a range of temperatures (Ta = 50, 60, 70, 80, 90, and 100 °C), and correspond to three different annealing times (ta = 1h, 2h, 3h). The effect on PPDO is investigated by using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), X-ray diffraction (XRD), and scanning electron microscopy (SEM). With an increase in Ta and ta, the grain size and the degree of crystallinity also increase. Meanwhile, the tensile strength is significantly improved. The PPDO bars (90 °C, 2 h) reach the maximum crystallinity (57.21%) and the maximum tensile strength (41.1 MPa). Interestingly, the heat treatment process does not result in serious thermal degradation.
    [Show full text]
  • Biocompatible Polymer Materials with Antimicrobial Properties for Preparation of Stents
    nanomaterials Review Biocompatible Polymer Materials with Antimicrobial Properties for Preparation of Stents KateˇrinaŠkrlová 1,2, KateˇrinaMalachová 3, Alexandra Muñoz-Bonilla 4 , Dagmar Mˇeˇrinská 5, Zuzana Rybková 3, Marta Fernández-García 4 and Daniela Plachá 1,6,* 1 Nanotechnology Centre, VŠB–Technical University of Ostrava, 17. listopadu 15, 708 00 Ostrava-Poruba, Czech Republic; [email protected] 2 Center of Advanced Innovation Technologies, VŠB–Technical University of Ostrava, 17. listopadu 15, 708 00 Ostrava-Poruba, Czech Republic 3 Department of Biology and Ecology, Faculty of Science, University of Ostrava, Chittussiho 10, 71000 Ostrava, Czech Republic; [email protected] (K.M.); [email protected] (Z.R.) 4 Institute of Polymer Science and Technology (ICTP-CSIC), Juan de la Cierva 3, 28001 Madrid, Spain; [email protected] (A.M.-B.); [email protected] (M.F.-G.) 5 Faculty of Technology, Tomas Bata University in Zlín, Vavreˇckova275, 760 01 Zlín, Czech Republic; [email protected] 6 ENET Centre, VŠB–Technical University of Ostrava, 17. listopadu 15, 708 00 Ostrava -Poruba, Czech Republic * Correspondence: [email protected]; Tel.: +420-596-991-557 Received: 26 September 2019; Accepted: 29 October 2019; Published: 31 October 2019 Abstract: Biodegradable polymers are promising materials for use in medical applications such as stents. Their properties are comparable to commercially available resistant metal and polymeric stents, which have several major problems, such as stent migration and stent clogging due to microbial biofilm. Consequently, conventional stents have to be removed operatively from the patient’s body, which presents a number of complications and can also endanger the patient’s life.
    [Show full text]
  • Fabrication of Tri-Layered Electrospun Polycaprolactone Mats With
    www.nature.com/scientificreports OPEN Fabrication of tri‑layered electrospun polycaprolactone mats with improved sustained drug release profle S. Manjunath Kamath1*, K. Sridhar5, D. Jaison4, V. Gopinath2, B. K. Mohamed Ibrahim5, Nilkantha Gupta1, A. Sundaram3, P. Sivaperumal6, S. Padmapriya7 & S. Shantanu Patil1 Modulation of initial burst and long term release from electrospun fbrous mats can be achieved by sandwiching the drug loaded mats between hydrophobic layers of fbrous polycaprolactone (PCL). Ibuprofen (IBU) loaded PCL fbrous mats (12% PCL‑IBU) were sandwiched between fbrous polycaprolactone layers during the process of electrospinning, by varying the polymer concentrations (10% (w/v), 12% (w/v)) and volume of coat (1 ml, 2 ml) in fanking layers. Consequently, 12% PCL‑ IBU (without sandwich layer) showed burst release of 66.43% on day 1 and cumulative release (%) of 86.08% at the end of 62 days. Whereas, sandwich groups, especially 12% PCLSW‑1 & 2 (sandwich layers—1 ml and 2 ml of 12% PCL) showed controlled initial burst and cumulative (%) release compared to 12% PCL‑IBU. Moreover, crystallinity (%) and hydrophobicity of the sandwich models imparted control on ibuprofen release from fbrous mats. Further, assay for cytotoxicity and scanning electron microscopic images of cell seeded mats after 5 days showed the mats were not cytotoxic. Nuclear Magnetic Resonance spectroscopic analysis revealed weak interaction between ibuprofen and PCL in nanofbers which favors the release of ibuprofen. These data imply that concentration and volume of coat in fanking layer imparts tighter control on initial burst and long term release of ibuprofen. Electrospinning has attracted extensive attention in the recent years, due to its facile nature and ability to rapidly synthesize fbrous mats for applications such as tissue engineering, wound dressing, fltration devices and drug delivery1–3.
    [Show full text]
  • Absorbable Sutures in General Surgery
    REVIEW ARTICLE Absorbable sutures in general surgery – review, available materials, and optimum choices Marcin Gierek1, Katarzyna Kuśnierz2, Paweł Lampe2, Gabriela Ochała3, Józef Kurek1, Bartłomiej Hekner4, Katarzyna Merkel5, Jakub Majewski1 1Department of General, Endocrine and Oncological Surgery, Multispecialty Hospital, Jaworzno; Head: Józef Kurek MD PhD 2Department of Gastrointestinal Tract Surgery, Medical University of Silesia, Katowice2 Head: Prof. Paweł Lampe MD PhD 3Department of Skin and Venereal Diseases, Municipal Hospital, Sosnowiec; Head: Anita Lenartowska-Białek MD 4Silesian University of Technology, Katowice; Head: Prof. Jerzy Myalski PhD 5Department of Material Engineering, Central Mining Institute, Katowice; Head: Henryk Rydarowski PhD Article history: Received: 17.01.2016 Accepted: 01.03.2017 Published: 30.04.2018 ABstract: Sutures are the most versatile materials used in surgery. Despite recent technological advances and availability of novel ma- terials such as tissue cements, it appears that surgical sutures will continue to be used for many years to come. The objective of this study was to provide an overview of the most common absorbable sutures used in general surgery. The appropriate su- ture choice for a particular procedure is of key importance for the success of that procedure. KEYWORDS: Absorbable sutures, Polydioxanone, Polyglecaprone, Polyglactin INTRODUCTION cenna (980-1037). Appropriate suture choice for a particular procedure is a pre- The 19th century was an era of catgut. Catgut is a biodegradable requisite for the success of that procedure. Sutures inappro- fiber characterized by good mechanical properties. priate for a particular organ may have tragic consequences for patients, as shown by Allan Oldfather Whipple in 1934 [1]. In 1868, Joseph Lister made the first attempt to use sutures coated Whipple used catgut as the suturing material in his first ampulla with an antibacterial agent.
    [Show full text]
  • Recent Applications of Polylactic Acid in Pharmaceutical and Medical Industries
    Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research, 2015, 7(12):51-63 ISSN : 0975-7384 Review Article CODEN(USA) : JCPRC5 Recent applications of polylactic acid in pharmaceutical and medical industries Ramzi A. Abd Alsaheb 1, Azzam Aladdin 1, Nor Zalina Othman 1, Roslinda Abd Malek 1, Ong Mei Leng 2, Ramlan Aziz 1 and Hesham A. El Enshasy 1,3* 1Institute of Bioproduct Development (IBD), Universiti Teknologi Malaysia (UTM), Skudai, Johor, Malaysia 2Harita Go Green Snd. Bhd., 75450 Ayer Keroh, Melaka, Malaysia 3City for Scientific Research and Technology Applications, New Burg Al Arab, Alexandria, Egypt _____________________________________________________________________________________________ ABSTRACT Polylactic acid (PLA) is a biodegradable polymer with special properties that has been studied intensively during the last decades. PLA is one of the most promising biopolymers used in nowadays and have large number of applications in food, packaging, medical and pharmaceutical industries. In addition, with the extensive use of exogenous implementation of different materials in human body for repair of different types of soft and hard tissues in many surgeries, there was enormous need to apply natural, biodegradable, non-inflammatory and biocompatible materials. PLA and its co-polymer composites showed superior characters over other materials in tissue engineering applications. This review is focused on providing comprehensive information about the most recent and promising applications of PLA in the pharmaceutical
    [Show full text]
  • Study of Non-Isothermal Crystallization of Polydioxanone and Analysis of Morphological Changes Occurring During Heating and Cooling Processes
    polymers Article Study of Non-Isothermal Crystallization of Polydioxanone and Analysis of Morphological Changes Occurring during Heating and Cooling Processes Yolanda Márquez 1,2, Lourdes Franco 1, Pau Turon 2, Juan Carlos Martínez 3 and Jordi Puiggalí 1,* 1 Chemical Engineering Department, Escuela d’Enginyeria Barcelona Est (EEBE), c/ Eduard Maristany 19, Barcelona 08930, Spain; [email protected] (Y.M.); [email protected] (L.F.) 2 B. Braun Surgical S.A., Carretera de Terrassa 121, Barcelona 08191, Spain; [email protected] 3 ALBA Synchrotron Light Facility, Ctra BP 1413 km 3.3, Cerdanyola del Vallès, Barcelona 08290, Spain; [email protected] * Correspondence: [email protected]; Tel.: +34-934-016684 Academic Editor: Naozumi Teramoto Received: 11 August 2016; Accepted: 19 September 2016; Published: 28 September 2016 Abstract: Non-isothermal crystallization kinetics of polydioxanone (PDO), a polymer with well-established applications as bioabsorbable monofilar suture, was investigated by Avrami, Mo, and isoconversional methodologies. Results showed Avrami exponents appearing in a relatively narrow range (i.e., between 3.76 and 2.77), which suggested a three-dimensional spherulitic growth and instantaneous nucleation at high cooling rates. The nucleation mechanism changed to sporadic at low rates, with both crystallization processes being detected in the differential scanning calorimetry (DSC) cooling traces. Formation of crystals was hindered as the material crystallized because of a decrease in the motion of molecular chains. Two secondary nucleation constants were derived from calorimetric data by applying the methodology proposed by Vyazovkin and Sbirrazzuoli through the estimation of effective activation energies. In fact, typical non-isothermal crystallization analysis based on the determination of crystal growth by optical microscopy allowed secondary nucleation constants of 3.07 × 105 K2 and 1.42 × 105 K2 to be estimated.
    [Show full text]
  • Small-Diameter Hybrid Vascular Grafts Composed of Polycaprolactone And
    www.nature.com/scientificreports OPEN Small-diameter hybrid vascular grafts composed of polycaprolactone and Received: 25 August 2016 Accepted: 5 May 2017 polydioxanone fibers Published: xx xx xxxx Yiwa Pan1, Xin Zhou1, Yongzhen Wei1, Qiuying Zhang1, Ting Wang2, Meifeng Zhu1, Wen Li1, Rui Huang1, Ruming Liu1, Jingrui Chen3, Guanwei Fan3, Kai Wang1, Deling Kong1 & Qiang Zhao1 Electrospun polycaprolactone (PCL) vascular grafts showed good mechanical properties and patency. However, the slow degradation of PCL limited vascular regeneration in the graft. Polydioxanone (PDS) is a biodegradable polymer with high mechanical strength and moderate degradation rate in vivo. In this study, a small-diameter hybrid vascular graft was prepared by co-electrospinning PCL and PDS fibers. The incorporation of PDS improves mechanical properties, hydrophilicity of the hybrid grafts compared to PCL grafts. The in vitro/vivo degradation assay showed that PDS fibers completely degraded within 12 weeks, which resulted in the increased pore size of PCL/PDS grafts. The healing characteristics of the hybrid grafts were evaluated by implantation in rat abdominal aorta replacement model for 1 and 3 months. Color Doppler ultrasound demonstrated PCL/PDS grafts had good patency, and did not show aneurysmal dilatation. Immunofluorescence staining showed the coverage of endothelial cells (ECs) was significantly enhanced in PCL/PDS grafts due to the improved surface hydrophilicity. The degradation of PDS fibers provided extra space, which facilitated vascular smooth muscle regeneration within PCL/PDS grafts. These results suggest that the hybrid PCL/PDS graft may be a promising candidate for the small-diameter vascular grafts. Cardiovascular disease (CVD) is the NO.1 killer in the world, and it is responsible for >17.3 million deaths every year, a number that represents 31% of all global deaths1.
    [Show full text]
  • Polydioxanone-Based Membranes for Bone Regeneration
    polymers Article Polydioxanone-Based Membranes for Bone Regeneration Sybele Saska 1,* , Livia Pilatti 1 , Edvaldo Santos de Sousa Silva 1, Magda Aline Nagasawa 1,2, Diana Câmara 3, Nelson Lizier 4, Eduardo Finger 5, Marta Dyszkiewicz Konwi ´nska 6 , Bartosz Kempisty 7,8,9, Samy Tunchel 1, Alberto Blay 1 and Jamil Awad Shibli 1,2,* 1 M3 Health Ind. Com. de Prod. Med. Odont. e Correlatos S.A., 640 Ain Ata, Jundiaí 13212-213, Brazil; [email protected] (L.P.); [email protected] (E.S.d.S.S.); [email protected] (M.A.N.); [email protected] (S.T.); [email protected] (A.B.) 2 Department of Periodontology and Oral Implantology, Dental Research Division, University of Guarulhos, Guarulhos 07023-070, Brazil 3 Nicell—Pesquisa e Desenvolvimento Ltd.a, 2721 Av. Indianápolis, São Paulo 04063-005, Brazil; [email protected] 4 CCB—Centro de Criogenia Brasil, 1861 Av. Indianápolis, São Paulo 04063-003, Brazil; [email protected] 5 Hospital Israelita Albert Einstein, 627 Av. Albert Einstein, São Paulo 05652-900, Brazil; fi[email protected] 6 Department of Anatomy, Pozna´nUniversity of Medical Sciences, 60-781 Poznan, Poland; [email protected] 7 Department of Histology and Embryology, Pozna´nUniversity of Medical Sciences, 60-781 Poznan, Poland; [email protected] 8 Department of Veterinary Surgery, Institute of Veterinary Medicine, Nicolaus Copernicus University in Toru´n, 87-100 Torun, Poland 9 Prestage Department of Poultry Science, North Carolina State University, Raleigh, NC 27695-7608, USA Citation: Saska, S.; Pilatti, L.; Silva, * Correspondence: [email protected] (S.S.); [email protected] (J.A.S.); Tel.: +55-11-3109-9045 (J.A.S.) E.S.d.S.; Nagasawa, M.A.; Câmara, D.; Lizier, N.; Finger, E.; Dyszkiewicz Abstract: Resorbable synthetic and natural polymer-based membranes have been extensively studied Konwi´nska,M.; Kempisty, B.; for guided tissue regeneration.
    [Show full text]
  • 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) ...........................................................................
    [Show full text]
  • Polymer Biomaterial Constructs for Regenerative
    POLYMER BIOMATERIAL CONSTRUCTS FOR REGENERATIVE MEDICINE AND FUNCTIONAL BIOLOGICAL SYSTEMS by LINGHUI MENG Submitted in partial fulfillment of the requirements For the degree of Doctor of Philosophy Dissertation Advisor: Dr. Gary E. Wnek Department of Macromolecular Science and Engineering CASE WESTERN RESERVE UNIVERSITY May, 2012 CASE WESTERN RESERVE UNIVERSITY SCHOOL OF GRADUATE STUDIES We hereby approve the thesis/dissertation of Linghui Meng s candidate for the Ph.D. degree *. (signed) Dr. Gary E. Wnek s (chair of the committee) Dr. David Schiraldi s Dr. Alexander M. Jamieson s Dr. Horst Von Recum s (date) 12/05/2011 s *We also certify that written approval has been obtained for any proprietary material contained therein. Table of Contents Chapter I Crosslinking and Modification of Collagen-based Materials ..................... 1 1.1 Introduction ............................................................................................................................ 1 1.2 Characteristics of Collagen as a Biomaterial ......................................................................... 2 1.2.1 Collagen Native Structures ............................................................................................. 2 1.2.2 Collagen Natural Crosslinks ........................................................................................... 6 1.3 Isolation and Purification of Collagen ................................................................................... 7 1.4 Exogeneous Crosslinking of Collagen ................................................................................
    [Show full text]
  • University of Groningen Synthesis and Properties of Starch Based
    University of Groningen Synthesis and properties of starch based biomaterials Sugih, Asaf Kleopas IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2008 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Sugih, A. K. (2008). Synthesis and properties of starch based biomaterials. s.n. Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date: 26-09-2021 Chapter 2 Experimental Studies on the Ring Opening Polymerization of p‐dioxanone using an Al(OiPr)3‐Monosaccharide Initiator System Abstract The ring opening polymerization (ROP) of p‐dioxanone using a protected i monosaccharide (1,2;3,4‐di‐O‐isopropylidene‐α‐D‐galactopyranose)/Al(O Pr)3 initiator system to yield polydioxanone with a protected monosaccharide end‐ group is described. The products were synthesized at 60‐100°C and characterized by 1H‐ and 13C‐NMR, and MALDI‐TOF mass spectrometry.
    [Show full text]