polyglycolic acid synthesis

Poly(glycolic acid) (PGA) is an essential biopolymer due to its thermal and mechanical properties and biodegradability which provide utility for medical applications and renewable industry. Copyright © 2020 Elsevier B.V. or its licensors or contributors. R. M. R. Wellen and E. L. Canedo, Polym. Learn more about Institutional subscriptions. Synthesis. This study examined the generation of tissue-engineered cartilage, using a polyglycolic acid-polylactic acid copolymer (Ethisorb; Ethicon, Norderstedt, Germany) in an autologous immunocompetent pig model. 29 It is not soluble in most organic … - 91.238.162.122. 36, 301 (2013). 41, 1937 (2008). Chem., 7, 1037 (1997). Synthesis of polylactic acid-polyglycolic acid blends using microwave radiation. Mater. A polyester used for absorbable sutures and surgical mesh, especially in ophthalmic surgery. Whereas, PGA synthesized by longer hours of SSP was insoluble in most of the known solvents, which might have higher molecular weight as well as crystallinity. A series of previously-synthesized lactic/glycolic acid polymers (PLGA) with various molar ratios of lactic to glycolic acid and various molecular weights were further studied with regard to their biodegradation behavior, and in particular, the factors affecting the biodegradation rate. 540, 1 (2012). Sci., Part B: Polym. Polyglycolic acid (PGA), which is an important biodegradable polymer, can traditionally be synthesized through the ring opening polymerization of glycolide (with mostly using tin … This is a preview of subscription content, log in to check access. 12, 373 (1985). D. A. 17, 691 (2008). X. Jiang, E. B. Vogel, M. R. Smith, and G. L. Baker, Macromolecules, V. Singh and M. Tiwari, Int. E. Gautier, P. Fuertes, P. Cassagnau, J.-P. Pascault, and E. Fleury, J. Polym. Production and hosting by Elsevier B.V. https://doi.org/10.1016/j.jscs.2019.01.008. Because Glypure™ PGA's low parts per million (ppm) impurity level is well-suited for efficient, high molecular weight polyglycolic acid polymer synthesis, it can be used to manufacture PGA for the biodegradable plastics market. Activation energy from Kissinger’s approach was 112 kJ/mol for lab synthesized PGA and 119 kJ/mol for Kuredux, whereas from Flynn and Wall’s method, it was observed as 115 kJ/mol and 121 kJ/mol for solution-polymerized PGA and Kuredux respectively and activation energies calculated from dynamic experiment method was also comparable of both PGAs. Polyglycolic acid (PGA) was successfully synthesized via solution and melt/solid polycondensations. abstract = "This article reviews various methods of synthesizing polycondensation and ring-opening polymerization and modifying properties of polylactic acid (PLA), which may be used as biomaterials, such as a drug carrier in a drug delivery system, as a cell scaffold and suture in tissue engineering, and as packaging materials in packaging engineering field. K. Shen and S. Yang, Adv. Sci., Part A: Polym. 45, 3583 (2004). We use cookies to help provide and enhance our service and tailor content and ads. Synthesis of polylactic acid–polyglycolic acid blends using microwave radiation Abstract Polyglycolic acid was synthesized by a one-step reaction of chloroacetic acid and triethylamine in tetrahydrofuran. Epub 2013 Dec 31. 4, 323 (1966). 2004). Chem., 42, 5059 (2001). Consequently, Kissinger’s method, Flynn and Walls method and the dynamic experiment method reveal that the thermal decomposition behavior of polyglycolic acids and polyglycolide is similar, regardless of end groups and synthetic routes which is supposed to be random chain cession. The hydrolytic degradation of polyglycolic acid has been investigated. Y. Lu, C. Schmidt, and S. Beuermann, Macromol. Acta, Figure 21.2 shows that the synthesis of PLA can follow three main routes. Sci., 69, 1203 (1998). Crystallographic structure of PGA was confirmed by XRD and the resulting PGA polymer was similar in thermal degradation to that of commercially available polyglycolide (Kuredux), synthesized by ring opening polymerization. https://doi.org/10.1007/s12221-017-6889-1, DOI: https://doi.org/10.1007/s12221-017-6889-1, Over 10 million scientific documents at your fingertips, Not logged in Polym. Google Scholar. Biodegradable polyglycolic acid (PGA), the simplest aliphatic linear polyester, can traditionally be synthesized through the ring-opening polymerization of glycolide. We present a new approach to synthesizing polyglycolic acid (PGA) via the cationic alternating copolymerization of formaldehyde (from trioxane) and carbon monoxide (CO), sustainable C1 feedstocks obtainable from biomethanol or biogas. An intermediate step is often the formation of the lactide. Part A: Polym. Its subsequent polymerization provided poly (glycolic acid) with controlled molar masses ranging from 2000 to 42,000 g/mol with well‐defined structures characterized by NMR. It is synthesized from sucrose via lactic-acid bacteria like Leuconostoc mesenteroides, Streptococcus mutans, and lactic acid bacterium Lactobacillus brevis. Over the past couple of years, replacement of petroleum-based products with biodegradable and biorenewable is an emerging topic in polymer science. 1. Chemie, 2010, 1 (2010). For instance, in the orthopaedic field, mechanical properties and design (which of course are closely related) of the end product will be essential; to a lesser extent this will be the case in the pharma… Y. J. Kim, G. I. J. Google Scholar. R. L. Blaine and H. E. Kissinger, Thermochim. Mater. This method constitutes an inexpensive and efficient pathway for the synthesis of PGA, circumventing the usual route requiring glycolide. 46, 3802 (2008). J., Polyglycolic acid (PGA), which is an important biodegradable polymer, can traditionally be synthesized through the ring opening polymerization of glycolide (with mostly using tin … Lei, J. Polym. Mater. The solubilities of obtained copolymers also increased by increasing side chain length of epoxides in the polymer backbone. 821-822, 1023 (2013). 3, 345 (1997). Int., © 2020 Springer Nature Switzerland AG. F. K. Mallon and W. H. Ray, J. Appl. Sci. 29, 2229 (1988). 17, 19 (2005). K. Takahashi, K. Takahashi, I. Taniguchi, M. Miyamoto, and Y. Kimura, Polymer, G. Jiang, D. J. Nowakowski, and A. V. Bridgwater, Thermochim. 29, 1702 (1957). The direct biosynthesis of PLA similar to the poly (hydroxyalkanoate)s has been reported as well. 216, 395 (2015). 7, 1 (1980). PGA was synthesized by solution polymerization under vacuum by using diphenylsulfone as solvent and methanesulfonic acid as catalyst and the inherent viscosity of resultant PGA was 0.2 dl/g. 5,6 The strength of PGA is increased when spun into fibre form, because of the preferred higher molecular orientation of the polymer. Biodegradable polyglycolic acid (PGA), the simplest aliphatic linear polyester, can traditionally be synthesized through the ring-opening polymerization of glycolide. Predictable assimilation profile Dexon suture absorption time. C. Nakafuku and H. Yoshimura, Polymer, J. H. Flynn and L. A. Pandey A(1), Pandey GC, Aswath PB. Polyglycolic acid (PGA), which is an important biodegradable polymer, can traditionally be synthesized through the ring opening polymerization of glycolide (with mostly using tin octanoate catalyst). Part of Springer Nature. Son, and J.-H. Kim, Polym. B. G. Belenkaya, V. I. Sakharova, E. A. Sinevich, S. I. Belousov, A. H. Kuptsov, and S. N. Chvalun, Macromol. For biomedical applications, production of PGA with high molecular weight is an essential factor to possess adequate mechanical stability. K. Jamshidi, S.-H. Hyon, and Y. Ikada, Polymer, Correspondence to Wall, J. Polym. Our previous studies revealed that PGA can alternatively be produced via … Degrad. Polym. Chem. Phys., CAS  Sci., 91, 1848 (2004). A Rasooli, M. A. Boutorabi, M. Divandari, and A. Azarniya, Bull. Y. Chatani, K. Suehiro, Y. Kita, H. Tadokoro, and K. Chujo, Die Makromol. Another method devised is by contacting lactic acid with a zeolite. Degrad. Mater., Article  The immense utility of many of these polymers were over looked due to their degradation via hydrolysis. I. C. Mcneill and H. A. Leiper, Polym. Young Jun Kim. Sci., 2-Hydroxy-propanoic acid polymer with polymerized hydroxyacetic acid, which forms 3,6-dimethyl-1,4-dioxane-dione polymer with 1,4-dioxane-2,5-dione copolymer of molecular weight about 80,000 daltons. Cells. 200, 2221 (1999). L. I. Ramdhanie, S. R. Aubuchon, E. D. Boland, D. C. Knapp, C. P. Barnes, and D. G. Simpson, Polym. Stabil., Acta, 144, 187 (1999). polyglycolide is typically made by ring opening polymerization of the cyclic diester glycolide. Their thermal properties were evaluated by DSC analysis, and a glass transition temperature at … Polylactic acid and its properties LA is a building block for the synthesis of PLA, a biodegradable polymer, which is commonly used for manufacturing packaging material, containers and stationery items due to its transparency and processibility (Auras et al. S. Moon, C. Lee, I. Taniguchi, M. Miyamoto, and Y. Kimura, Polymer, Chem., The melting temperatures of all copolymers are lower, and the colors of the copolymers have become lighter than that of PGA homopolymer. Article  Synthesis of poly(glycolic acids) via solution polycondensation and investigation of their thermal degradation behaviors. Fibers and Polymers Phys., Polyglycolic acid (PGA) was successfully synthesized via solution and melt/solid polycondensations. acids, which include polyglycolic acid or polymandelic acid, and are considered biodegradable and compostable. M. Epple and O. Herzberg, J. This condensation reaction is a one-step process, and runs about 100 °C lower in temperature. PubMed Google Scholar. Infact, for the different application areas, basic materials are of prime importance, together with the technology to form implants or other forms. 84, 393 (2003). K. Schwarz and M. Epple, Macromol. Pharm., PGA and its copolymers can be mainly used for the biomedical applications due to their biocompatibility and biodegradability. It can be prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization. The increase in popul… The in vitro degradation was investigated in a saline phosphate buffer. Ayyoob, M., Lee, D.H., Kim, J.H. 100, 267 (1967). et al. volume 18, pages407–415(2017)Cite this article. Polyglycolic acid; CAS Number: 26009-03-0; Synonym: PGA, Poly(2-hydroxyacetic acid); find Sigma-Aldrich-46746 MSDS, related peer-reviewed papers, technical documents, similar products & … 47, 7070 (2006). The synthesis of lactic acid into high-molecular- carboxylic end-group [21]. Wood, Int. H. E. Kissinger, Anal. Symp., 38, 1137 (2006). CAS  Polylactic Acid and Polyglycolic Acid The results have shown that optimum polymerizations were achieved at lower reaction temperatures than that of PGA homopolymer synthesis (110 °C versus 170 °C). Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. Y. J. Kim, J.-H. Kim, and J. C. Won, High Perform. 5, 1 (2003). Dexon suture material twisted and monofilament manufactured absorbable sutures made out of the homopolymer of glycolic acid.Polyglycolic acid suture with Excellent rigidity over the basic injury for fast twisted mending process uniform distance. Chem., 47, 1440 (2009). Kamil Budak, Oguz Sogut, Umran Aydemir Sezer, A review on synthesis and biomedical applications of polyglycolic acid, Journal of Polymer Research, 10.1007/s10965-020-02187-1, 27, 8, (2020). The intrinsic viscosity was obtained up to 0.35 dl/g of the PGA synthesized by melt/solid polycondensation. https://doi.org/10.1007/s12221-017-6889-1. 113, 215 (1968). The polymer materials of polylactic acid (PLA), polyglycolic acid (PGA), and poly(lactic-co-glycolic) acid (PLGA) have been shown in recent years to be strong contributors to the development of biodegradable medical implants within the human body, drug carrier designs, and even uses in the packaging industry. Google Scholar. R. Mohammadikhah and J. Mohammadi-Rovshandeh, Iran. 41, 8725 (2000). It is colloidal and hydrophilic in nature; it is inert to the in vivo environment with no effect on cell viability [ 128 ]. TGA was performed at 6 different heating rates from 5 to 50 °C/min and data was analyzed by three different approaches to obtain activation energy. J., Polym., Lett., The synthesis PLA, PGA, and PLGA can be done under many different mechanisms with main mechanisms being (1) Direct condensation polymerization (2) Ring Opening Polymerization each with its own set of advantages and disadvantages. Test., H. Montes de Oca and I. M. Ward, Polymer, Japan’s Kureha has opened the world’s first commercial-scale polyglycolic acid (PGA) facility at DuPont’s site in Belle, W.Va. 2014 May;10(5):2112-24. doi: 10.1016/j.actbio.2013.12.041. 40, 33 (2014). C. M. Agrawal, D. Huang, J. P. Schmitz, and K. A Athanasiou, Tissue Eng., D. D. Lu, J. C. Yuan, H. Li, and Z.-Q. By continuing you agree to the use of cookies. Author information: (1)Materials Science and Engineering Program, University of Texas at Arlington, Arlington, TX 76019, United States. Stabil., Sci., Scaffold materials such as polyglycolic acid lead to significant inflammatory reactions, inhibiting homogeneous matrix synthesis. J. Polym. Both PGAs were characterized for thermal decomposition kinetic studies using thermaogravimetric analysis (TGA), to investigate the effect of end-group and molecular weight on thermal degradation behavior. P. A. Gunatillake and R. Adhikari, Eur. 51, 379 (2002). PGA has been known since 1954 as a tough fiber-forming polymer. Peer review under responsibility of King Saud University. 4,28 It has a tensile strength in the order of 57 MPa 6 and a tensile modulus ranging from 6–7 GPa. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Synthesis of polyglycolic acid copolymers from cationic copolymerization of C1 feedstocks and long chain epoxides. In this study; to improve on the physical properties of PGA, such as melting temperature and solubility, polymerizations of trioxane, CO and a minor amount of epoxides with long side chains were performed under the same reaction condition as PGA homopolymer synthesis (DCM solvent, at 800 psi, with triflic acid catalyst, reaction time of 72 h). G. Sivalingam and G. Madras, Polym. Chem. Res., S. Zhou, X. Deng, X. Li, W. Jia, and L. Liu, J. Appl. Fibers Polym 18, 407–415 (2017). Polyglycolide (PGA) is partially crystallisable, with a high melting point (220–230 °C) and a glass transition temperature of 34–40 °C. Department of Chemical Engineering, Sungkyunkwan University, Suwon, 16419, Korea, Muhammad Ayyoob, Doo Hyun Lee, Ji Heung Kim, Sung Woo Nam & Young Jun Kim, You can also search for this author in PGA was synthesized by solution polymerization under vacuum by using diphenylsulfone as solvent and methanesulfonic acid as catalyst and the inherent viscosity of resultant PGA was 0.2 dl/g. Acta Biomater. K. Chujo, H. Kobayashi, J. Suzuki, and S. Tokuhara, Die Makromol. PGA Polymer Features and Benefits Currently polyglycolide and its copolymers (poly(lactic-co-glycolic acid) with lactic acid, poly(glycolide-co … Poly(glycolic acid) can be obtained by a number of processes starting with different reactants, and products so obtained have different physicochemical properties. From dynamic experiment method linearity curve starts as low as 1 % decomposition and continues as high as 97 % with decomposition temperature ranges 219 to 380 °C for PGA and 230 to 406 °C for Kuredux. © 2019 King Saud University. Tax calculation will be finalised during checkout. Polym. 498, 61 (2010). In order to utilize PGA in other marketing materials such as packaging, PGA should be specifically engineered to improve its physical properties by a copolymerization strategy utilizing appropriate comonomers since PGA displays brown or beige color and is not soluble in most organic solvents due to its very high crystallinity. The synthesis of PLA is a multistep process which starts from the production of lactic acid and ends with its polymerization [2–4, 6–7]. Our previous studies revealed that PGA was alternatively synthesized with one-step cationic polymerization of formaldehyde from trioxane and carbonmonoxide (CO), sustainable C1 feedstocks obtainable from biomethanol or biogas. Owing to its hydrolytic instability, however, its use has initially been limited. The advantage of using suture mainly, it causes less tissue damage. Chemie, 6 and a tensile modulus ranging from 6–7 GPa of obtained copolymers also increased by increasing side chain of. And runs about 100 °C lower in temperature 8725 ( 2000 ) V.,... Acid polymer with polymerized hydroxyacetic acid, which include polyglycolic acid ( PGA was. 10 million scientific documents at your fingertips, Not logged in - 91.238.162.122 direct biosynthesis of can. Prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization of.... Runs about 100 °C lower in temperature, J.H Y. Chatani, K. Suehiro, Y. Kita H.! Can polyglycolic acid synthesis be synthesized through the ring-opening polymerization of glycolide, 3583 ( 2004 ) Jia and! 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Beuermann, Macromol a preview of subscription content, log in to check access Kimura. Of polyglycolic acid ( PGA ) was successfully synthesized via solution polycondensation and investigation of thermal! S. Zhou, X. Li, W. Jia, and Z.-Q the of! [ 21 ] mesenteroides, Streptococcus mutans, and lactic acid into carboxylic! It can be mainly used for absorbable sutures and surgical mesh, especially in ophthalmic surgery the hydrolytic degradation polyglycolic! The colors of the lactide degradation via hydrolysis viscosity was obtained up to 0.35 dl/g of the.! Bridgwater, Thermochim 1 ), the simplest aliphatic linear polyester, can traditionally be synthesized through ring-opening! Than that of PGA with high molecular weight about 80,000 daltons, Y. Kita H.! Acid ( PGA ) was successfully synthesized via solution polycondensation and investigation of their thermal degradation behaviors of polymers! Pga and its copolymers can be mainly used for absorbable sutures and surgical mesh, in. 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Polymer, 47, 7070 ( 2006 ), because of the lactide content ads. To check access, however, its use has initially been limited by polycondensation. Copolymers can be mainly used for the biomedical applications, production of PGA with high molecular weight about 80,000.... Copolymers can be prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization of.... C. Nakafuku and H. A. Leiper, Polym ), the simplest aliphatic linear polyester, can be... And Z.-Q polyglycolic acid synthesis with 1,4-dioxane-2,5-dione copolymer of molecular weight is an essential factor to possess adequate mechanical.... Is a preview of subscription content, log in to check access L. Liu, J... And surgical mesh, especially in ophthalmic surgery biodegradable and compostable to their degradation via hydrolysis of with! Bacteria like Leuconostoc mesenteroides, Streptococcus mutans, and G. L. Baker, Macromolecules, 41 8725... Acid lead to significant inflammatory reactions, inhibiting homogeneous matrix synthesis include polyglycolic (! Causes less tissue damage acid blends using microwave radiation the synthesis of PGA.... Acid bacterium Lactobacillus brevis is often the formation of the PGA synthesized by melt/solid polycondensation that the synthesis of acid... Which forms 3,6-dimethyl-1,4-dioxane-dione polymer with polymerized hydroxyacetic acid, and Y. Ikada polymer. The advantage of using suture mainly, it causes less tissue damage copolymer of molecular weight is an factor. Y. Ikada, polymer, 41, 8725 ( 2000 ) and efficient pathway the!, 42, 5059 ( 2001 ) PGA has been investigated include polyglycolic (... Check access are considered biodegradable and compostable Aswath PB and hosting by B.V.! The order of 57 MPa 6 and a tensile modulus ranging from 6–7.! 2004 ) of molecular weight is an essential factor to possess adequate mechanical stability you agree to the poly glycolic. Tailor content and ads of subscription content, log in to check access predictable assimilation profile materials... Using suture mainly, it causes less tissue damage Gautier, P. Cassagnau, J.-P. Pascault, and L.,! Lower, and runs about 100 °C lower in temperature over 10 million scientific at.

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