Abstract
Enzymatic hydrolytic degradation of polybutylene succinate (PBS), poly(polybutylenesuccinate-co-1,4-cyclohexane dimethanol) (PBS/CHDM) and poly(polybutylene succinate-co-diglycolic acid) (PBS/DGA) in mixed solvent of tetrahydrofuran (THF) and toluene was examined. Lipase was used as catalyst to degrade polymers with molecular weight of more than 100,000, and the molecular weight of products ranged from hundreds to thousands. Thermal decomposition temperatures of all products were below 250°C. The degradation products of both PBS/CHDM and PBS/DGA showed two melting points at about 85 and 99°C. Mass spectrometry (MS) was employed to obtain the molecular weight of oligomers extracted from the products, which proved to be low-polyesters with the molecular weight of less 1,000. The butanediol (BDO) monomer was found in PBS/CHDM degradation product for the first time.
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Abbreviations
- PBS:
-
Polybutylene succinate
- PBS/CHDM:
-
Poly(polybutylene succinate-co-1,4-cyclohexane dimethanol)
- PBS/DGA:
-
Poly(polybutylene succinate-co-diglycolic acid)
- SA:
-
Succinate
- BDO:
-
Butanediol
- CHDM:
-
1,4-Cyclohexane dimethanol
- DGA:
-
Diglycolic acid
References
Abou-Zeid DM, Müller RJ, Deckwer WD (2004) Biodegradation of aliphatic homopolyesters and aliphatic–aromatic copolyesters by anaerobic microorganisms. Biomacromolecules 5:1687–1697
Azim H, Dekhterman A et al (2006) Candida antarctica lipase B-catalyzed synthesis of poly (butylene succinate): shorter chain building blocks also work. Biomacromolecules 7:3093–3097
Chen Y, Jia Z, Schaper A, Kristiansen M (2004) Hydrolytic and enzymatic degradation of liquid–crystalline aromatic/aliphatic copolyesters. Biomacromolecules 5:11–16
He F, Li S, Vert M, Zhuo R (2003) Enzyme-catalyzed polymerization and degradation of copolymers prepared from e-caprolactone and poly (ethylene glycol). Polymer 44:5145–5151
He F, Li S, Garreau H, Vert Michel, Zhuo R (2005) Enzyme-catalyzed polymerization and degradation of copolyesters of ε-caprolactone and γ-butyrolactone. Polymer 46:12682–12688
Hoshino A, Isono Y (2002) Degradation of aliphatic polyester films by commercially available lipases with special reference to rapid and complete degradation of poly (l-lactide) film by lipase PL derived from Alcaligenes sp. Biodegradation 13:141–147
Kurokawa K, Yamashita K, Doi Y, Abe H (2008) Structural effects of terminal groups on nonenzymatic and enzymatic degradations of end-capped poly (l-lactide). Biomacromolecules 9:1071–1078
Lenglet S, Li S, Vert M (2009) Lipase-catalyzed degradation of copolymers prepared from 3-caprolactone and dl-lactide. Polym Degrad Stab 94(4):688–692
Li S, Liu L, Garreau H (2003) Lipase-catalyzed biodegradation of poly (ε-caprolac tone) blended with various polylactide-based polymers. Biomacromolecules 4:372–377
Marcilla R, de Geus M, Mecerreyes D (2006) Enzymatic polyester synthesis in ionic liquids. Eur Polym J 42:1215–1221
Massardier-Nageotte V, Pestre C, Cruard-Pradet T (2006) Aerobic and anaerobic biodegradability of polymer films and physico-chemical characterization. Polym Degrad Stab 91(3):620–627
Min Z, Shuili L, Jie S (2008) Copolymerization and modification of biodegradable poly (butylene succinate) by 1,4-CHDM. Chem J Chin Univ 29(6):1246–1249
Okajima S, Kondo R, Toshima K (2003) Lipase-catalyzed transformation of poly (butylene adipate) and poly (butylene succinate) into repolymerizable cyclic oligomers. Biomacromolecules 4:1514–1519
Rizzarelli P, Impallomeni G (2004) Biomacromolecules 5:433–444
Ronkvist AM, Xie W, Lu W, Gross RA (2009) Cutinase-catalyzed hydrolysis of poly (ethylene terephthalate). Macromolecules 42:5128–5138
Rosario Vidal, Pilar Martínez, Elena Mulet (2007) Environmental assessment of biodegradable multilayer film derived from carbohydrate polymers. J Polym Environ 15:159–168
Shuai X, Jedlinski Z, Kowalczuk M, Rydz J (1999) Enzymatic synthesis of polyesters from hydroxyl acids. Eur Polym J 35:721–725
Soledad Marque’s-Calvo M, Cerdà-Cue’llar Marta, Kint DPR (2006) Enzymatic and microbial biodegradability of poly (ethylene terephthalate) copolymers containing nitrated units. Polym Degrad Stab 91(4):663–671
Tokiwa Y, Calabia BP (2007) Biodegradability and biodegradation of polyesters. J Polym Environ 15:259–267
Uyama H, Kobayashi S (2002) Enzyme-catalyzed polymerization to functional polymers. J Mol Catal B 19–20:117–127
Acknowledgments
The author thanks National Natural Science Foundation of China and Zhejiang Wenzhou Research Institute of Light Industry for their financial support. This project was supported by the Graduate Innovation Fund of Shaanxi University of Science and Technology and Key Laboratory of Auxiliary Light Chemical Industry in Shaanxi Province.
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Ding, M., Zhang, M., Yang, J. et al. Study on the enzymatic degradation of PBS and its alcohol acid modified copolymer. Biodegradation 23, 127–132 (2012). https://doi.org/10.1007/s10532-011-9492-y
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DOI: https://doi.org/10.1007/s10532-011-9492-y