• [Review]
  • Precise Polymerization Control and Applications of Polyvinyl Acetate

  • Seulah Lee# , Sungyoung Yoon# , and Jongbok Lee†

  • Department of Biological and Chemical Engineering, Hongik University, Sejong 30016, Korea

  • 폴리비닐아세테이트의 정밀한 중합 제어 및 응용

  • 이슬아# · 윤성영# · 이종복†

  • 홍익대학교 바이오화학공학과

  • Reproduction, stored in a retrieval system, or transmitted in any form of any part of this publication is permitted only by written permission from the Polymer Society of Korea.

References
  • 1. Joseph, A.; Mathai, A. E.; Thomas, S. Sorption and Diffusion of Methyl Substituted Benzenes Through Cross-linked Nitrile Rubber/poly(ethylene co-vinyl acetate) Blend Membranes. J. Membr. Sci. 2003, 220, 13-30.
  •  
  • 2. Chung, J. W.; Oh, K. S.; Kwak, S. Y. Evaluation of the Degree of Exfoliation in Poly(e-caprolactone)/Organoclay Nanocomposites Based on Viscoelastic Relaxation. Macromol. Mater. Eng. 2007, 292, 627-633.
  •  
  • 3. Cherifi, B. I.; Belbachir, M.; Rahmouni, A. Green Anionic Polymerization of Vinyl Acetate Using Maghnite-Na+ (Algerian MMT): Synthesis Characterization and Reactional Mechanism. Discov. Chem. Eng. 2021, 1.
  •  
  • 4. Chinchkar, A. V.; Singh, A.; Singh, R.; Kamble, M. G.; Dar, A. H.; Sagar, N. A. Effect of Polyvinyl Acetate (PVAc) Based Coating on Quality Characteristics of Capsicum During Storage. J. Food. Sci. Technol. 2023, 60, 1077-1087.
  •  
  • 5. Koo, G.-H.; Yoon, S.-J.; Jang, J. Preparation of Superabsorbent PVA Films with Polycarboxylic Acid Crosslinkers. Text. Color. and Finish. 2009, 21, 39-45.
  •  
  • 6. Di, X.; Ma, Q.; Xu, Y.; Yang, M.; Wu, G.; Sun, P. High-performance ionic Conductive Poly(vinyl alcohol) Hydrogels for Flexible Strain Sensors Based on a Universal Soaking Strategy. Mater. Chem. Front. 2021, 5, 315-323.
  •  
  • 7. Lim, J. I. Drug-Releasing Type Teeth Anti-Aging Coating Agent Using Shellac and Polyvinyl Acetate Composites. Polym. Korea. 2023, 47, 326-331.
  •  
  • 8. Joo, Y. S.; Cha, J. R.; Gong, M. S. Preparation of Cool-off Type Thermosensitive Adhesives Based on a Vinyl Acetate and Their Properties. Polym. Korea. 2018, 42, 729-735.
  •  
  • 9. Lee, K. Y.; Mooney, D. J. Hydrogels for Tissue Engineering. Chem. Rev. 2001, 101, 1869-1880.
  •  
  • 10. Theis, A.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C. Probing the Reaction Kinetics of Vinyl Acetate Free Radical Polymerization via Living Free Radical Polymerization (MADIX). Polymer 2006, 47, 999-1010.
  •  
  • 11. Kawai, F.; Hu, X. Biochemistry of Microbial Polyvinyl Alcohol Degradation. Appl. Microbiol. Biotechnol. 2009, 84, 227-237.
  •  
  • 12. Kawagoshi, Y.; Fujita, M. Purification and Properties of the Polyvinyl Alcohol-degrading Enzyme 2, 4-pentanedione Hydrolase Obtained from Pseudomonas Vesicularis var. Povalolyticus PH. World J. Microbiol. Biotechnol. 1997, 14, 95-100.
  •  
  • 13. Nord, F. Dehydrogenation Activity of Fusarium Lini B. Sci. Nat. 1936, 24, 10.1007.
  •  
  • 14. Ben Halima, N. Poly(vinyl alcohol): Review of Its Promising Applications and Insights Into Biodegradation. RSC Advances 2016, 6, 39823-39832.
  •  
  • 15. Marušincová, H.; Husárová, L.; Růžička, J.; Ingr, M.; Navrátil, V.; Buňková, L.; Koutny, M. Polyvinyl Alcohol Biodegradation Under Denitrifying Conditions. Int. Biodeterior. Biodegrad. 2013, 84, 21-28.
  •  
  • 16. Min, L.; Zhang, D.; Du, G.; Chen, J. Enhancement of PVA-degrading Enzyme Production by the Application of pH Control Strategy. J. Microbiol. Biotechnol. 2012, 22, 220-225.
  •  
  • 17. Watanabe, Y.; Morita, M.; Hamada, M.; Tsujisaka, Y. Studies on the Polyvinyl Alcohol-degrading Enzyme. Part 1. Purification and Properties of a Polyvinyl Alcohol-degrading Enzyme Produced by a Strain of Pseudomonas. Arch. Biochem. Biophys. 1976, 174, 573-579.
  •  
  • 18. Shimao, M.; Fukuta, I.; Kato, N.; Sakazawa, C. Mixed Continuous Cultures of Polyvinyl Alcohol-utilizing Symbionts Pseudomonas Putida VM15A and Pseudomonas sp. Strain VM15C. Appl. Environ. Microbiol. 1984, 48, 751-754.
  •  
  • 19. Suzuki, T.; Tsuchii, A. Degradation of Diketones by Polyvinyl Alcohol-degrading Enzyme Produced by Pseudomonas sp. Process Biochem. 1983, 18, 13-16.
  •  
  • 20. Chiellini, E.; Corti, A.; D'Antone, S.; Solaro, R. Biodegradation of Poly(vinyl alcohol) Based Materials. Prog. Polym. Sci. 2003, 28, 963-1014.
  •  
  • 21. Lyoo, W. Poly(vinyl alcohol) Functional Materials. Fiber. Technol. Ind. 2002, 6, 96-123.
  •  
  • 22. Miyazaki, T.; Katayama, S.; Funai, E.; Tsuji, Y.; Sakurai, S. Role of Adsorbed Iodine Into Poly(vinyl alcohol) Films Drawn in KI/I2 solution. Polymer 2005, 46, 7436-7442.
  •  
  • 23. Ham, S. K.; Jung, M. H.; Chang, J. H. Blend Films of Poly(acrylic acid-co-maleic acid) with Poly(vinyl alcohol) (I) : Thermo-mechanical Properties and Gas Permeability. Polym. Korea 2006, 30, 298-304.
  •  
  • 24. Karakus, G.; Polat, Z. A.; Yenidunya, A. F.; Zengin, H. B.; Karakus, C. B. Synthesis, Characterization and Cytotoxicity of Novel Modified Poly[(maleic anhydride)-co-(vinyl acetate)]/noradrenaline conjugate. Polym. Int. 2012, 62, 492-500.
  •  
  • 25. Yang, D.-Y.; Liu, Q.-X.; Xie, X.-L.; Zeng, F.-D. Structure and Thermal Properties of Exfoliated PVC/layered Silicate Nanocomposites via in situ Polymerization. J. Therm. Anal. Calorim. 2006, 84, 355-359.
  •  
  • 26. Lozinsky, V. I.; Vainerman, E. S.; Domotenko, L. V.; Mamtsis, A. M.; Titova, E. E.; Belavtseva, E. M.; Rogozhin, S. V. Study of Cryostructurization of Polymer Systems VII. Structure Formation Under Freezing of Poly(vinyl alcohol) Aqueous Solutions. Colloid. Polym. Sci. 1986, 264, 19-24.
  •  
  • 27. Braunecker, W. A.; Matyjaszewski, K. Controlled/living Radical Polymerization: Features, Developments, and Perspectives. Prog. Polym. Sci. 2007, 32, 93-146.
  •  
  • 28. Guan, Y.; Li, J.; Shao, L.; Wang, F.; Dong, D.; Wang, Y. Controlled Synthesis of Poly(vinyl acetate) by Traditional Radical Emulsion Polymerization. Polym. Int. 2016, 65, 1382-1386.
  •  
  • 29. Davidson, R.; Bartholomew, R. The Photosensitized Oxidation of Amines. Part I. The Use of Benzophenone as a Sensitiser. J. Chem. Soc. C 1971, 12, 2342-2346.
  •  
  • 30. Decker, C.; Jenkins, A. D. Kinetic Approach of Oxygen Inhibition in Ultraviolet-and Laser-induced Polymerizations. Macromolecules 1985, 18, 1241-1244.
  •  
  • 31. Goto, A.; Fukuda, T. Kinetics of Living Radical Polymerization. Prog. Polym. Sci. 2004, 29, 329-385.
  •  
  • 32. Greszta, D.; Mardare, D.; Matyjaszewski, K. “Living” Radical Polymerization. 1. Possibilities and Limitations. Macromolecules 1994, 27, 638-644.
  •  
  • 33. Matyjaszewski, K. Atom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives. Macromolecules 2012, 45, 4015-4039.
  •  
  • 34. Truong, N. P.; Jones, G. R.; Bradford, K. G. E.; Konkolewicz, D.; Anastasaki, A. A Comparison of RAFT and ATRP Methods for Controlled Radical Polymerization. Nat. Rev. Chem. 2021, 5, 859-869.
  •  
  • 35. Hawker, C. J.; Bosman, A. W.; Harth, E. New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations. Chem. Rev. 2001, 101, 3661-3688.
  •  
  • 36. Likhtenshtein, G. I. Nitroxide-Mediated Polymerization. In Nitroxides Brief History, Fundamentals, and Recent Developments; Springer: 2020; pp161-186.
  •  
  • 37. Mardare, D.; Matyjaszewski, K. “Living” Radical Polymerization of Vinyl acetate. Macromolecules 1994, 27, 645.
  •  
  • 38. Yoshida, E. Nitroxide-mediated Photo-living Radical Polymerization of Vinyl Acetate. Colloid. Polym. Sci. 2009, 288, 73-78.
  •  
  • 39. Krishna Rao, K. S. V.; Kummara, M. R. A Review on Radical Polymerization Used for Design and Development of Biomaterials by NOVA Publications. In Radical Polymerization: New Developments; I. O. P. a. L. A. Urbonas; NOVA Publications: 2012; pp175-198.
  •  
  • 40. Kamigaito, M.; Ando, T.; Sawamoto, M. Metal-Catalyzed Living Radical Polymerization. Chem. Rev. 2001, 101, 3689-3746.
  •  
  • 41. Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. Synthesis of well defined polymers by Controlled Radical Polymerization. Macromol. Symp. 1995, 98, 73-89.
  •  
  • 42. Tang, W.; Fukuda, T.; Matyjaszewski, K. Reevaluation of Persistent Radical Effect in NMP. Macromolecules 2006, 39, 4332-4337.
  •  
  • 43. Kim, S. Synthesis of Block Copolymer of Polystyrene and Polyethylene Glycol Methyl Ether Methacrylate(PEGMA) by ATRP(atom transfer radical polymerization). J. Korean Appl. Sci. and Tech. 2009, 26, 306-316.
  •  
  • 44. Koumura, K.; Satoh, K.; Kamigaito, M. Manganese-Based Controlled/Living Radical Polymerization of Vinyl Acetate, Methyl Acrylate, and Styrene: Highly Active, Versatile, and Photoresponsive Systems. Macromolecules 2008, 41, 7359-7367.
  •  
  • 45. Koumura, K.; Satoh, K.; Kamigaito, M.; Okamoto, Y. Iodine Transfer Radical Polymerization of Vinyl Acetate in Fluoroalcohols for Simultaneous Control of Molecular Weight, Stereospecificity, and Regiospecificity. Macromolecules 2006, 39, 4054-4061.
  •  
  • 46. Champouret, Y.; MacLeod, K. C.; Smith, K. M.; Patrick, B. O.; Poli, R. Controlled Radical Polymerization of Vinyl Acetate with Cyclopentadienyl Chromium β-Diketiminate Complexes: ATRP vs. OMRP. Organometallics 2010, 29, 3125-3132.
  •  
  • 47. Tang, H.; Radosz, M.; Shen, Y. Atom Transfer Radical Polymerization and Copolymerization of Vinyl Acetate Catalyzed by Copper Halide/terpyridine. AIChE 2009, 55, 737-746.
  •  
  • 48. Kermagoret, A.; Chau Ndo, Q.; Grignard, B.; Cordella, D.; Debuigne, A.; Jerome, C.; Detrembleur, C. Cobalt-Mediated Radical Polymerization of Vinyl Acetate and Acrylonitrile in Supercritical Carbon Dioxide. Macromol. Rapid Commun. 2016, 37, 539-544.
  •  
  • 49. Morin, A. N.; Detrembleur, C.; Jérôme, C.; De Tullio, P.; Poli, R.; Debuigne, A. Effect of Head-to-Head Addition in Vinyl Acetate Controlled Radical Polymerization: Why Is Co(acac)2-Mediated Polymerization so Much Better? Macromolecules 2013, 46, 4303-4312.
  •  
  • 50. Debuigne, A.; Champouret, Y.; Jerome, R.; Poli, R.; Detrembleur, C. Mechanistic Insights Into the Cobalt-mediated Radical Polymerization (CMRP) of Vinyl Acetate with Cobalt(III) Adducts as Initiators. Chem. Eur. J. 2008, 14, 4046-4059.
  •  
  • 51. Enikolopyan, N. S.; Smirnov, B. R.; Ponomarev, G. V.; Belgovskii, I. M. Catalyzed Chain Transfer to Monomer in Free Radical Polymerization Polym. Chem. 1981, 19, 879-889.
  •  
  • 52. Debuigne, A.; Caille, J.-R.; Jérôme, R. Highly Efficient Cobalt-Mediated Radical Polymerization of Vinyl Acetate. Angew. Chem. Int. Ed. 2005, 44, 1101-1104.
  •  
  • 53. Debuigne, A.; Poli, R.; Jérôme, C.; Jérôme, R.; Detrembleur, C. Overview of Cobalt-mediated Radical Polymerization: Roots, State of the Art and Future Prospects. Prog. Polym. Sci. 2009, 34, 211-239.
  •  
  • 54. Rayna Bryaskova; Christophe Detrembleur; Antoine Debuigne; R. Jéroˆme. Cobalt-Mediated Radical Polymerization (CMRP) of Vinyl Acetate Initiated by Redox Systems: Toward the Scale-Up of CMRP. Macromolecules 2006, 39, 8263-8268.
  •  
  • 55. Benchaphanthawee, W.; Peng, C. H. Organo-Cobalt Complexes in Reversible-Deactivation Radical Polymerization. Chem. Rec. 2021, 21, 3628-3647.
  •  
  • 56. Wang, F. S.; Yang, T. Y.; Hsu, C. C.; Chen, Y. J.; Li, M. H.; Hsu, Y. J.; Chuang, M. C.; Peng, C. H. The Mechanism and Thermodynamic Studies of CMRP: Different Control Mechanisms Demonstrated by CoII(TMP), CoII(salen*), and CoII(acac) 2 Mediated Polymerization, and the Correlation of Reduction Potential, Equilibrium Constant, and Control Mechanism. Macromol. Chem. Phys. 2016, 217, 422-432.
  •  
  • 57. Sabzevari, A.; Dadkhah, A. S.; Kohestanian, M.; Mahdieh, A.; Semsarzadeh, M. A. Cobalt-mediated Radical Polymerization of Vinyl Acetate in a Packed Column System: Simultaneous Effective Control of Molecular Weight, Separation, and Purification. J. Polym. Res. 2022, 29.
  •  
  • 58. Tian, X.; J. Ding; B. Zhang; F. Qiu; X. Zhuang; Y. Chen. Recent Advances in RAFT Polymerization: Novel Initiation Mechanisms and Optoelectronic Applications. Polymers 2018, 10, 318.
  •  
  • 59. Zard, S. Z. Discovery of the RAFT/MADIX Process: Mechanistic Insights and Polymer Chemistry Implications. Macromolecules 2020, 53, 8144-8159.
  •  
  • 60. Ding, C.; Fan, C.; Jiang, G.; Pan, X.; Zhang, Z.; Zhu, J.; Zhu, X. Photocatalyst-Free and Blue Light-Induced RAFT Polymerization of Vinyl Acetate at Ambient Temperature. Macromol. Rapid Commun. 2015, 36, 2181-2185.
  •  
  • 61. Hedayati, H. R.; Khorasani, M.; Ahmadi, M.; Ballard, N. Preparation of Well-defined Poly(Vinyl alcohol) by Hydrolysis of Poly(Vinyl acetate) Synthesized by RAFT Suspension Polymerization. Polymer 2022, 246, 124674.
  •  
  • 62. Corpart, P.; Charmot, D.; Zard, S. Z.; Biadatti, T.; Michelet, D. Method for Block Polymer Synthesis by Controlled Radical Polymerisation. US Patent 6,153,705, 2000.
  •  
  • 63. Chiefari, J.; Mayadunne, R. T.; Moad, G.; Rizzardo, E. Polymerization Process with Living Characteristics and Polymers Made Therefrom. US Patent 6,642,318 B1, 2003.
  •  
  • 64. Stenzel, M. H.; Cummins, L.; Roberts, G. E.; Davis, T. P.; Vana, P.; Barner-Kowollik, C. Xanthate Mediated Living Polymerization of Viny Acetate: A Systematic Variation in MADIX/RAFT Agent Structure. Macromol. Chem. Phys. 2003, 204, 1160-1168.
  •  
  • 65. Benaglia, M.; Chiefari, J.; Chong, Y. K.; Moad, G.; Rizzardo, E.; Thang, S. H. Universal (switchable) RAFT agents. J. Am. Chem. Soc. 2009, 131, 6914-6915.
  •  
  • 66. Keddie, D. J.; Guerrero-Sanchez, C.; Moad, G.; Mulder, R. J.; Rizzardo, E.; Thang, S. H. Chain Transfer Kinetics of Acid/base Switchable N-aryl-N-pyridyl Dithiocarbamate RAFT Agents in Methyl Acrylate, N-vinylcarbazole and Vinyl Acetate Polymerization. Macromolecules 2012, 45, 4205-4215.
  •  
  • 67. Matioszek, D.; Brusylovets, O.; Wilson, D. J.; Mazières, S.; Destarac, M. Reversible Addition–fragmentation Chain-transfer Polymerization of Vinyl Monomers with N, N-dimethyldiselenocarbamates. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4361-4368.
  •  
  • 68. Matioszek, D.; Mazières, S.; Brusylovets, O.; Lin, C. Y.; Coote, M. L.; Destarac, M.; Harrisson, S. Experimental and Theoretical Comparison of Addition–Fragmentation Pathways of Diseleno- and Dithiocarbamate RAFT Agents. Macromolecules 2019, 52, 3376.
  •  
  • 69. Zhan, Y.; Zhang, Z.; Pan, X.; Zhu, J.; Zhou, N.; Zhu, X. A Cyclic Selenium-based Reversible Addition-fragmentation Chain Transfer Agent Mediated Polymerization of Vinyl Acetate. J. Polym. Sci. 2013, 51, 1656.
  •  
  • 70. Destarac, M.; Charmot, D.; Franck, X.; Zard, S. Z. Dithiocarbamates as Universal Reversible Addition-fragmentation Chain Transfer Agents. Macromol. Rapid Commun. 2000, 21, 1035-1039.
  •  
  • 71. Phommalysack-Lovan, J.; Chu, Y.; Boyer, C.; Xu, J. PET-RAFT Polymerisation: Towards Green and Precision Polymer Manufacturing. Chem. Commun. 2018, 54, 6591-6606.
  •  
  • 72. Shanmugam, S.; Xu, J.; Boyer, C. Utilizing the Electron Transfer Mechanism of Chlorophyll a Under Light for Controlled Radical Polymerization. Chem. Sci. 2015, 6, 1341-1349.
  •  
  • 73. Xu, J.; Jung, K.; Atme, A.; Shanmugam, S.; Boyer, C. A Robust and Versatile Photoinduced Living Polymerization of Conjugated and Unconjugated Monomers and Its Oxygen Tolerance. JACS 2014, 136, 5508-5519.
  •  
  • 74. Lee, Y.; Boyer, C.; Kwon, M. S. Photocontrolled RAFT Polymerization: Past, Present, and Future. Chem. Soc. Rev. 2023, 52, 3035-3097.
  •  
  • 75. Allegrezza, M. L.; Konkolewicz, D. PET-RAFT Polymerization: Mechanistic Perspectives for Future Materials. ACS Macro. Lett. 2021, 10, 433-446.
  •  
  • 76. Fu, C.; Xu, J.; Tao, L.; Boyer, C. Combining Enzymatic Monomer Transformation with Photoinduced Electron Transfer−reversible Addition–fragmentation Chain Transfer for the Synthesis of Complex Multiblock Copolymers. ACS Macro. Lett. 2014, 3, 633-638.
  •  
  • 77. Shanmugam, S.; Xu, J.; Boyer, C. Photoinduced Electron Transfer–reversible Addition–fragmentation Chain Transfer (PET-RAFT) Polymerization of Vinyl Acetate and N-Vinylpyrrolidinone: Kinetic and Oxygen Tolerance Study. Macromolecules 2014, 47, 4930-4942.
  •  
  • 78. Nagao, M.; Horie, A.; Matsumoto, H.; Hoshino, Y.; Miura, Y. Continuous-flow PET-RAFT Polymerization in a Packed-Bed Reactor with Porphyrin-Immobilized Silica Particles. Ind. Eng. Chem. Res. 2023, 63, 200-209.
  •  
  • 79. Corrigan, N.; Zhernakov, L.; Hashim, M. H.; Xu, J.; Boyer, C. Flow Mediated Metal-free PET-RAFT Polymerisation for Upscaled and Consistent Polymer Production. React. Chem. Eng. 2019, 4, 1216-1228.
  •  
  • 80. Rong, L. H.; Caldona, E. B.; Advincula, R. C. PET-RAFT Polymerization Under Flow Chemistry and Surface-initiated Reactions. Polym. Int. 2023, 72, 145-157.
  •  
  • 81. Micic, N.; Young, A.; Rosselgong, J.; Hornung, C. H. Scale-up of the Reversible Addition-Fragmentation Chain Transfer (RAFT) Polymerization Using Continuous Flow Processing. Processes 2014, 2, 58-70.
  •  
  • 82. Wenn, B.; Junkers, T. Continuous Microflow Photo RAFT Polymerization. Macromolecules 2016, 49, 6888-6895.
  •  
  • 83. Corrigan, N.; Rosli, D.; Jones, J. W. J.; Xu, J.; Boyer, C. Oxygen Tolerance in Living Radical Polymerization: Investigation of Mechanism and Implementation in Continuous Flow Polymerization. Macromolecules 2016, 49, 6779-6789.
  •  
  • 84. Railian, S.; Wenn, B.; Junkers, T. Photo-induced Copper-Mediated Acrylate Polymerization in Continuous-flow Reactors. J. Flow Chem. 2016, 6, 260-267.
  •  
  • 85. Amann, M.; O. Minge Biodegradability of Poly(vinyl acetate) and Related Polymers. In Synthetic Biodegradable Polymers; A. K. Bernhard Rieger, Geoffrey W. Coates, Robert Reichardt, Eckhard Dinjus, Thomas A. Zevaco; Springer: 2012; pp137-172.
  •  
  • 86. Delplace, V.; Nicolas, J. Degradable Vinyl Polymers for Biomedical Applications. Nat. Chem. 2015, 7, 771-784.
  •  
  • 87. Agarwal, S.; Kumar, R.; Kissel, T.; Reul, R. Synthesis of Degradable Materials Based on Caprolactone and Vinyl Acetate Units Using Radical Chemistry. Polym. J. 2009, 41, 650-660.
  •  
  • 88. Mulchandani, N.; Narayan, R. Redesigning Carbon–Carbon Backbone Polymers for Biodegradability–Compostability at the End-of-Life Stage. Molecules 2023, 28, 3832.
  •  
  • 89. Kim, Y. H.; Om, C. Y.; Hwang, Y. S.; Hong, Y. B. Adhesive Properties of Water-soluble and Biodegradable Hot-melt Adhesive Based on Partially Saponified Poly(vinyl acetate). Mater. Res. Express 2020, 7, 075301.
  •  
  • 90. Mothe, S. R.; Ang, P.; Lau, H. H.; Oh, A. B. Y.; Thoniyot, P. Investigating the Potential of Degradable Poly(vinyl acetate) Copolymer Microparticles for Encapsulation and in vitro Release Studies. Next Mater. 2023, 1, 100055.
  •  
  • 91. Schneider, C.; Langer, R.; Loveday, D.; Hair, D. Applications of Ethylene Vinyl Acetate Copolymers (EVA) in Drug Delivery Systems. J. Control. Release. 2017, 262, 284-295.
  •  
  • 92. He, W.; Zhao, Z.; Yuan, J.; Xiao, F. Recent Development of Ethylene–vinyl Acetate Modified Asphalt. Constr. Build. Mater. 2023, 363, 129800.
  •  
  • 93. Wang, C.; Zhang, Y.; Wang, Z. Mechanical Properties, Morphology, and Mullins Effect of Thermoplastic Vulcanizates Based on Ethylene–vinyl Acetate Copolymer/ethylene–vinyl Acetate Rubber. J. Thermoplast. Compos. Mater. 2017, 30, 827-839.
  •  
  • 94. Son, C. E.; Choi, S.-S. Characterization of Poly(ethylene-co-vinyl acetate)(EVA) Using Thermal Analytical Techniques. Elast. Compos. 2019, 54, 61-69.
  •  
  • 95. Meszlényi, G.; Körtvélyessy, G. Direct Determination of Vinyl Acetate Content of Ethylene-vinyl Acetate Copolymers in Thick Films by Infrared Spectroscopy. Polym. Test. 1999, 18, 551-557.
  •  
  • 96. Kost, J.; Wolfrum, J.; Langer, R. Magnetically Enhanced Insulin Release in Diabetic Rats. J. Biomed. Mater. Res. 1987, 21, 1367-1373.
  •  
  • 97. Creque, H. M.; Langer, R.; Folkman, J. One Month of Sustained Release of Insulin From a Polymer Implant. Diabetes 1980, 29, 37-40.
  •  
  • 98. Langer, R.; Folkman, J. Polymers for the Sustained Release of Proteins and Other Macromolecules. Nature 1976, 263, 797-800.
  •  
  • 99. Prykhodko, Y.; Martin, A.; Oulyadi, H.; Marais, S.; Fatyeyeva, K. Polymer EVA-OH Membrane with Improved Water/gas Separation Performance: Influence of VAc/VOH Repeating Units Ratio on Membrane Physical Chemical Properties. J. Membr. Sci. 2023, 673, 121386.
  •  
  • 100. Vaidya, S.; Tozer, K. R.; Chen, J. An Overview of Embolic Agents. Semin. Interv. Radiol. 2008, 25, 204-215.
  •  
  • 101. Esquivel, C.; J. Antonio; Guadalupe; M. Guerrero-Avendaño; Enríquez-García; Rocío. Influencia de Los Materiales Embolizantes en el Tamaño de Los Miomas Posterior a La Embolización de Arterias Uterinas. An. radiol. Méx. 2018, 17, 3-9.
  •  
  • 102. Rowe, R. C.; P. Sheskey; M. Quinn Polyvinyl Alcohol. In Handbook of Pharmaceutical Excipients 6th Edition; the Pharmaceutical Press: UK, 2009; pp564-565.
  •  
  • 103. Korelc, K.; Larsen, B. S.; Heintze, A.-L.; Henrik-Klemens, Å.; Karlsson, J.; Larsson, A.; Tho, I. Towards Personalized Drug Delivery via Semi-solid Extrusion: Exploring Poly(vinyl alcohol-co-vinyl acetate) Copolymers for Hydrochlorothiazide-loaded Films. Eur. J. Pharm. Sci. 2024, 192, 106645.
  •  
  • 104. Alassaf, M.; Alqahtani, S. M.; Al Khulaifi, R. S.; Saeed, W. S.; Alsubaie, F. S.; Semlali, A.; Aouak, T. Mevacor/Poly(vinyl acetate/2-hydroxyethyl methacrylate) as Solid Solution: Preparation, Solubility Enhancement and Drug Delivery. Polymers 2023, 15.
  •  
  • 105. Sengupta, D.; Lu, L.; Gomes, D. R.; Jayawardhana, B.; Pei, Y.; Kottapalli, A. G. P. Fabric-like Electrospun PVAc–graphene Nanofiber Webs as Wearable and Degradable Piezocapacitive Sensors. ACS Appl. Mater. Interfaces 2023, 15, 22351-22366.
  •  
  • 106. Ko, S.; Kim, S. Research on Capacitive Tactile Sensor for Electronic Skin using Natural Rubber and Nitrile Butadiene Rubber. Elast. Compos. 2023, 58, 173-178.
  •  
  • 107. Chen, J.; Zhu, Y.; Chang, X.; Pan, D.; Song, G.; Guo, Z.; Naik, N. Recent Progress in Essential Functions of Soft Electronic Skin. Adv. Funct. Mater. 2021, 31, 2104686.
  •  
  • 108. Yang, G.; Liao, D.; Chen, A.; Li, C.; Bashir, M. S. Preparation of Poly(vinyl alcohol) with Enhanced Stereoselectivity via Hydrolysis of Poly(vinyl acetate) Produced by Radical Polymerization Using 7-membered Ring Controlling Agents. J. Mol. Struct. 2024, 1302, 137474.
  •  
  • 109. Ohgi, H.; Sato, T.; Hu, S.; Horii, F. Highly Isotactic Poly(vinyl alcohol) Derived From Tert-butyl Vinyl Ether. Part IV. Some Physical Properties, Structure and Hydrogen Bonding of Highly Isotactic Poly(vinyl alcohol) Films. Polymer 2006, 47, 1324-1332.
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  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2023 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2025; 49(1): 1-16

    Published online Jan 25, 2025

  • 10.7317/pk.2025.49.1.1
  • Received on Sep 12, 2024
  • Revised on Nov 26, 2024
  • Accepted on Dec 6, 2024

Correspondence to

  • Jongbok Lee

  • Department of Biological and Chemical Engineering, Hongik University, Sejong 30016, Korea

  • E-mail: jlee0917@hongik.ac.kr