Abstract
This chapter deals with the biodegradability of vinyl ester-based polymers with a special emphasis on poly(vinyl acetate) and poly(vinyl alcohol). A proper discussion of the importance of the biodegradability of a certain polymer class cannot be made without understanding the impact that polymer class has on the environment. Therefore, apart from discussing the actual biodegradation mechanisms, other issues will be addressed. These include, but are not limited to, how long the class of vinyl ester-based polymers has been known and produced on an industrial scale, what quantities are produced and released into the environment each year, and what applications are addressed with this polymer class. We will also look at the general physical and chemical properties of this polymer class and how these properties can influence biodegradability. After a discussion of what “biodegradability” actually means – and what not – the mechanisms for the biodegradation of poly(vinyl ester)s will be discussed in more detail and a summary given of the biological systems able to process poly(vinyl ester)s.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Klatte F (1912) “Verfahren zur Herstellung technisch wertvoller Produkte aus organischen Vinylestern”, German Patent DP271381
Finch CA (1973) Polyvinyl alcohol. Wiley Interscience, New York
Staudinger H (1919) Über hochpolymere Verbindungen. Schweiz Chem Z 3:1–5, 28–33, 60–64
Staudinger H (1920) Über hochpolymere Verbindungen. Ber Dtsch Chem Ges 53:1073
Herrmann WO (1963) Vom Ringen mit den Molekülen. Econ-Verlag, Dusseldorf
Herrmann WO, Haehnel W (1925) “Polymerisation von Vinylestern”, German Patent DE490041
Hermann WO, Haehnel W (1924) “Verfahren zur Herstellung von polymerem Vinylalkohol”, German Patent DE450286
Hermann WO, Haehnel W (1926) “Alcohol Production”, Canadian Patent 265172
Staudinger H (1926) Über hochpolymere Verbindungen. Chem Ber 59:3019
Halle F, Hofmann W (1935) Faserdiagramme von Polyvinylalkohol. Naturwissens 23:770
Kim N, Sudol ED, Friedel P, El-Aasser MS (2003) Poly(vinyl alcohol) stabilization of acrylic emulsion polymers using the miniemulsion approach. Macromolecules 36:5573–5579
Nichols RT, Sowers RM (2009) Laminated materials, glass. Kirk-Othmer encyclopedia of chemical technology, Wiley, Weinheim, 1–17. doi: 10.1002/0471238961.1201130914090308
Tecnon OrbiChem (2007) S/Db-CHEM: acetic acid & vinyl acetate. Tecnon OrbiChem, London
Baerns M, Behr A, Brehm A, Gmehling J, Hofmann H, Onken U, Renken A (2006) Technische Chemie 1, Wiley-VCH, 573
Malveda M, Funada C (2010) Acetic acid. Chemical economics handbook report. SRI Consulting, Englewood
Weissermel K, Arpe HJ (1997) Industrial organic chemistry, 3rd edn. VCH, Weinheim, p 228
Nuyken O, Kricheldorf HR, Swift G (eds) (2005) Handbook of polymer synthesis. Marcel Dekker, New York
Henderson AM (1993) Ethylene-vinyl acetate (EVA) copolymers: a general review. Electrical Insulation Magazine 9:30–38
Chin H, Kälin T, Yokose K (2008) Polyvinyl acetate. Chemical economics handbook report. SRI Consulting, Englewood
Eubeler JP, Bernhard M, Zok S, Knepper TN (2009) Environmental biodegradation of synthetic polymers I. Test methodologies and procedures. Trends Anal Chem 28:1057–1072
Eubeler JP, Bernhard M, Zok S, Knepper TN (2010) Environmental biodegradation of synthetic polymers II. Biodegradation of different polymer groups. Trends Anal Chem 29:84–99
Lucas N, Bienaime C, Belloy C, Queneudec M, Silvestre F, Nava-Saucedo JE (2008) Polymer biodegradation: mechanisms and estimation techniques. Chemosphere 73:429–442
Giardina P, Faraco V, Pezzella V, Piscitelli A, Vanhulle S, Sannia G (2010) Laccases: a never-ending story. Cell Mol Life Sci 67:369–385
Endres HJ, Siebert-Raths A (2009) Polyvinylalkohole. In: Technische Biopolymere. Hanser, München, pp 176–182
Aso J, Miyamoto Y, Harada KM et al (2006) Engineered membrane superchannel improves bioremediation potential of dioxin-degrading bacteria. Nature Biotechnology 24:188–189
Vaclavkova J, Ruzicka J, Julinova M, Vicha R, Koutny M (2007) Novel aspects of symbiotic poly(vinyl alcohol) biodegradation. Appl Microbiol Biotechnol 76:911–917
Chiellini E, Corti A, Politi B, Solaro R (2000) Adsorption/desorption of polyvinyl alcohol on solid substrates and relevant biodegradation. J Polym Environ 8:67–79
Solaro R, Corti A, Chiellini E (2000) Biodegradation of poly(vinyl alcohol) with different molecular weights and degree of hydrolysis. Polym Adv Technol 11:873–878
Kawai F, Hu X (2009) Biochemistry of microbial polyvinyl alcohol degradation. Appl Microbiol Biotechnol 84:227–237
Sakai K, Fukuba M et al (1998) Purification and characterization of an esterase involved in poly(vinyl alcohol) degradation by Pseudomonas vesicularis PD. Biosci Biotechnol Biochem 62:2000–2007
Haschke H, Tomka I, Keilbach A (1998) Systematische Untersuchungen zur biologischen Abbaubarkeit von Verpackungsmaterial, 2.Mitt. Zur biologischen Abbaubarkeit von auf Polyvinylalkohol basierenden Verpackungsfolien. Monatsh Chem 129:365–386
Haschke H, Tomka I, Keilbach A (1998) Systematische Untersuchungen zur biologischen Abbaubarkeit von Verpackungsmaterial, 1.Mitt Zur tatsächlichen biologischen Abbaubarkeit von sogenannten bioabbaubaren Kunststofffolien. Monatsh Chem 129:253–279
Haschke H, Tomka I, Keilbach A (1998) Systematische Untersuchungen zur biologischen Abbaubarkeit von Verpackungsmaterial, 3.Mitt Neue Polyvinylalokohol-Stärke-Acetal-Folien. Monatsh Chem129:487–507
Matsumura S, Shimura Y, Terayama K, Kiyohara T (1994) Effects of molecular weight and stereo regularity on biodegradation of poly(vinyl alcohol) by Alcaligenes faecalis. Biotechnol Lett 16:1205–1210
Chiellini E, Corti A, Del Sarto G, D’Antone S (2006) Oxo-biodegradable polymers – effect of hydrolysis degree o biodegradation behaviour of poly(vinyl alcohol). Polym Degrad Stab 91:3397–3406
Zhang Y, Du G, Fan X, Chen J (2008) Effects and statistical optimization of fermentation conditions on growth and poly(vinyl alcohol) – degrading enzyme production of Streptomyces venezuelae GY1. Biocatal Biotransform 26:430–436
Corti A, Solaro R, Chiellini E (2002) Biodegradation of poly(vinyl alcohol) in selected mixed microbial culture and relevant culture filtrate. Polym Degrad Stab 75:447–458
Chiellini E, Corti AD’Antone S, Solaro R (2003) Biodegradation of poly(vinyl alcohol) based materials. Prog Polym Sci 28:963–1014
Cheng Q (2010) Green nanocomposites reinforced with cellulosic crystals isolated from juvenile poplar. In: Proceedings International Convention of Society of Wood Science and Technology and United Nations Economic Commission for Europe – Timber Committee October 11–14, Geneva, Switzerland, Paper NT-6 1
Julinova M, Kupec J et al (2010) Lignin and starch as potential inductors for biodegradation of films based on poly(vinyl alcohol) and protein hydrolysate. Polym Degrad Stab 95:225–233
Das K, Ray D et al (2010) Preparation and characterization of cross-linked starch/poly(vinyl alcohol) green films with low moisture absorption. Ind Eng Chem Res 49:2176–2185
Russo M, O’Sullivan C et al (2009) The anaerobic degradability of thermoplastic starch: Polyvinyl alcohol blends: Potential biodegradable food packaging materials. Bioresour Technol 100:1705–1710
Taghizadeh M, Abbasi Z (2010) Enzymatic degradation of starch/PVA composite film containing Montmorillonite nanoparticles. In: Proceedings 13th Asia Pacific Confederation of APCChE 2010 Chemical Engineering Congress October 5–8, Taipei
Peesan M, Rujiravanit R, Supaphol P (2003) Characterisation of beta-chitin/poly(vinyl alcohol) blend films. Polym Test 22:381–387
Kang YO, Yoon IS et al (2010) Chitosan-coated poly(vinyl alcohol) nanofibers for wound dressings. J Biomed Mater Res Part B: Appl Biomater 92B:568–576
Sua J-F, Yuanb XY et al (2010) Properties stability and biodegradation behaviors of soy protein isolate/poly(vinyl alcohol) blend films. Polym Degrad Stab 95:1226–1237
Matsumura S, Ii S, Shigeno H, Tanaka T, Okuda F, Shimura Y, Toshima K (1993) Molecular design of biodegradable functional polymers, 3. Biodegradability and functionality of poly[(sodium acrylate)-co-(vinyl alcohol)]. Die Makromolekulare Chemie 194:3237–3246
Argade A, Peppas N (1998) Poly(acrylic acid)–poly(vinyl alcohol) copolymers with superabsorbent properties. J Appl Polym Sci 70:817–829
Polinas (2003) EVOH-based barrier film, Polibarr (Tradename). Material safety data sheeet (91/155/EEC) MSDS No C2003/003. Available at http://www.polinas.com/grafik/File/msds/evoheng.pdf. Last accessed 16 Aug 2011
Arboleda C, Mejia AI, Lopez O (2004) Poly(vinylalcohol-co-ethylene) biodegradation on semi solid fermentation by Phanerochaete chrysosporium. Acta Farm Bonaerense 23(2):123–128
Simmons S, Thomas EL (1995) Structural characteristics of biodegradable thermoplastic starch/poly(ethylene–vinyl alcohol) blends. J Appl Polym Sci 58:2259–2285
Bastioli C (1998) Properties and applications of Mater-Bi starch-based materials. Polym Degrad Stab 59:263–272
Araújo MA, Cunha AM, Mota M (2010) Changes on surface morphology of corn starch blend films. J Biomed Mater Res A 94A:720–729
Matsumura S (2003) Biodegradation of poly(vinylalcohol) and its copolymers. In: Matsumura S, Steibüchel A (eds) Biopolymers, vol 9. Wiley VCH, Weinheim, pp 331–368
Kim MN, Yoona MG (2010) Isolation of strains degrading poly(vinyl alcohol) at high temperatures and their biodegradation ability. Polym Degrad Stab 95:89–93
Yamatsu A, Matsumi R, Atomi H, Imanaka T (2006) Isolation and characterization of a novel poly(vinylalcohol)-degrading bacterium, Sphingopyxis sp. PVA3. Appl Microbiol Biotechnol 72:804–811
Fukae R, Fujii T et al (1994) Biodegradation of poly(vinyl alcohol) with high isotacticity. Polym J 26:1381–1386
Hatanaka T, Kawahara T, Asahi N, Tsuji M (1995) Effects of the structure of poly(vinyl alcohol) on the dehydrogenation reaction by poly(vinyl alcohol) dehydrogenase from Pseudomonas sp. 113P3 T. Biosci Biotechnol Biochem 59:1229–1231
Lee J-A, Kim M-N (2003) Isolation of new and potent poly(vinyl alcohol)-degrading strains and their degradation activity. Polym Degrad Stab 81:303–308
Qian D, Du G, Chen J (2004) Isolation and culture characterization of a new polyvinyl alcohol-degrading strain Penicillium sp. WSH02-21. World J Microbiol Biotechnol 20:587–591
Lim JG, Park DH (2001) Degradation of polyvinyl alcohol by Brevibacillus laterosporus. J Microbiol Biotechnol 11:928–933
Zhang Y, Li Y (2006) A new strain, Streptomyces venezuelae GY1, producing a poly(vinyl alcohol)-degrading enzyme. World J Microbiol Biotechnol 22:625–628
Shimao M, Fukuta I et al (1984) Mixed continuous cultures of polyvinyl alcohol-utilizing symbionts Pseudomonas putida VM15A and Pseudomonas sp. strain VM15C. Appl Environ Microbiol 48:751–754
Mori T, Sakimoto M et al (1996) Isolation and characterization of a strain of Bacillus megaterium that degrades poly(vinyl alcohol). Biosci Biotechnol Biochem 60:330–332
Kim BC, Sohn CK, Lim SK et al (2003) Degradation of polyvinyl alcohol by Sphingomonas sp. SA3 and its symbiote. J Microbiol Biotechnol 30:70–74
Chen J, Zhang Y et al (2007) Biodegradation of polyvinyl alcohol by a mixed microbial culture. Enzyme Microb Technol 40:1686–1691
Pointing SB (2001) Feasibility of bioremediation by white-rot fungi. Appl Microbiol Biotechnol 57:20–33
Huang MH, Shih YP, Liu SM (2002) Biodegradation of polyvinyl alcohol by Phanerochaete chrysosporium after pretreatment with Fenton's reagent. J Environ Sci Health A Tox Hazard Subst Environ Eng 37:29–41
Chiellini E, Corti A, Solero R (1999) Biodegradation of poly(vinyl alcohol) based blown films under different environmental conditions. Polym Degrad Stab 64(2):305–312
Schonberger H, Baumann A, Keller W, Pogopetris P (1997) Study of microbial degradation of polyvinyl alcohol (PVA) in wastewater treatment plants. American Dyestuff Reporter August 1997:9-18. Available at http://www.p2pays.org/ref/02/01722.pdf. Last accessed 16 Aug 2011
Matsumura S, Kurita H, Shimokobe H (1993) Anaerobic biodegradability of polyvinyl alcohol. Biotechnol Lett 15:749–754
Ilcim M et al (2010) FT-IR study of gamma-radiation induced degradation of polyvinylalcohol (PVA) and PVA/humic acids blends. J Radioanal Nucl Chem 283:9–13
Mori T, Sakimoto M et al (1998) Secondary alcohol dehydrogenase from a vinyl alcohol oligomer-degrading Geotrichum fermentans; stabilization with Triton X-100 and activity toward polymers with polymerization degrees less than 20. World J Microbiol Biotechnol 14:349–356
Matsumura S, Tomizawa N et al. (1999) Novel poly(vinyl alcohol)-degrading enzyme and the degradation mechanism. Macromolecules 32:7753–7761
Hirota-Mamoto R, Nagai R, Tachibana S, Yasuda M, Tani A, Kimbara K, Kawai F (2006) Cloning and expression of the gene for periplasmic poly(vinyl alcohol) dehydrogenase from Sphingomonas sp. strain 113P3, a novel-type quinohaemoprotein alcohol dehydrogenase. Microbiology 152:1941–1949
Kawai F (2010) The biochemistry and molecular biology of xenobiotic polymer degradation by microorganisms. Biosci Biotechnol Biochem 74:1743–1759
Morozova OV, Shumakovich GP et al (2007) Laccase–mediator systems and their applications: a review. Appl Biochem Microbiol 43:523–535
Oh S-Y, Kim H-W, Park J-M, Park H-S, Yoon C (2009) Oxidation of polyvinyl alcohol by persulfate activated with heat, Fe2+, and zero-valent iron. J Hazard Mater 168:346–351
Lopez BL et al (1999) Biodegradability of poly(vinyl alcohol). Polym Eng Sci 39:1346–1352
Sakai K, Hamada N, Watanabe Y (1984) Non-enzymatic degradation of secondary alcohol oxidase-oxidized poly(vinyl alcohol). Agric Biol Chem 48:1093–1095
Kawagoshi Y, Fujita M (1998) Purification and properties of the polyvinyl alcohol-degrading enzyme 2,4-pentanedione hydrolase obtained from Pseudomonas vesicularis var. povalolyticus PH. World J Microbiol Biotechnol 14:95–100
Sakai K, Hamada N, Watanabe Y (1986) Degradation mechanism of poly(vinyl alcohol) by successive reactions of secondary alcohol oxidase and β-diketone hydrolase from Pseudomonas sp. Agric Biol Chem 50:989–996
Grogan G (2005) Emergent mechanistic diversity of enzyme- catalyzed beta-diketone cleavage. Biochem J 388:721–730
Klomklang W, Tani A et al (2005) Biochemical and molecular characterization of a periplasmic hydrolase for oxidized polyvinyl alcohol from Sphingomonas sp. strain 113P3. Microbiology 151:1255–1262
Skals PB, Krabek A, Nielsen PH, Wenzel H (2008) Environmental assessment of enzyme assisted processing in pulp and paper industry. Int J LCA 13:124–132
Ronkvist M, Lu W, Feder D, Gross R (2009) Cutinase-catalyzed deacetylation of poly(vinyl acetate). Macromolecules 42:6086–6097
Shimao M, Onishi S, Kato N, Sakazawa C (1989) Pyrroloquinoline quinone-dependent cytochrome reduction in polyvinyl alcohol-degrading Pseudomonas sp. strain VM15C. Appl Environ Microbiol 55:275–278
Shimao M, Tamogami T, Nishi K, Harayama S (1996) Cloning and characterization of the gene encoding pyrroloquinoline quinone-dependent poly(vinyl alcohol) dehydrogenase of Pseudomonas sp. strain VM15C. Biosci Biotechnol Biochem 60:1056–1062
Shimao M, Tamogami T, Kishida S, Harayama S (2000) The gene pvaB encodes oxidized polyvinyl alcohol hydrolase of Pseudomonas sp. strain VM15C and forms an operon with the poly-vinyl alcohol dehydrogenase gene pvaA. Microbiology 146:649–657
Mamoto R, Hu X, Chiue H, Fujioka Y, Kawai F (2008) Cloning and expression of soluble cytochrome c and its role in poly-vinyl alcohol degradation by polyvinyl alcohol-utilizing Sphingopyxis sp. strain 113P3. J Biosci Bioeng 105:147–151
Hu X, Mamoto R, Fujioka Y, Tani A, Kimbara K, Kawai F (2008) The pva operon is located on the megaplasmid of Sphingopyxis sp. strain 113P3 and is constitutively expressed, although expression is enhanced by PVA. Appl Microbiol Biotechnol 78:685–893
Tang B, Liaoa X et al (2010) Enhanced production of poly(vinyl alcohol)-degrading enzymes by mixed microbial culture using 1,4-butanediol and designed fermentation strategies. Polym Degrad Stab 95:557–563
Ishigaki T, Sugano W, Nakanishi A, Tateda M, Ike M, Fujita M (2004) The degradability of biodegradable plastics in aerobic and anaerobic waste landfill model reactors. Chemosphere 54:225–233
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2011 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Amann, M., Minge, O. (2011). Biodegradability of Poly(vinyl acetate) and Related Polymers. In: Rieger, B., Künkel, A., Coates, G., Reichardt, R., Dinjus, E., Zevaco, T. (eds) Synthetic Biodegradable Polymers. Advances in Polymer Science, vol 245. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2011_153
Download citation
DOI: https://doi.org/10.1007/12_2011_153
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-27153-3
Online ISBN: 978-3-642-27154-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)