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Biodegradable Photo-Crosslinked Thin Polymer Networks Based on Vegetable Oil Hydroxy Fatty Acids

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  • Published:
Journal of the American Oil Chemists' Society

Abstract

Novel crosslinked thin polymer networks based on vegetable oil hydroxy fatty acids (HFAs) were prepared by UV photopolymerization and their mechanical properties were evaluated. Two raw materials, castor oil and 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) were used as sources of mono- and di-HFAs, respectively. Poly(ethylene glycol) (PEG) diacrylate and poly(ε-caprolactone) diacrylate were synthesized and used as crosslinking agents to form crosslinked polymer networks by UV-initiated free-radical polymerization with acrylated castor oil or acrylated DOD. The synthesis of acrylate derivatives was confirmed using FT-IR and 1H-NMR spectroscopic techniques. The composition of the reaction mixture and the type/length of crosslinking agent were changed to obtain crosslinked polymer networks with various mechanical properties. For polymers prepared from high molecular weight (20,000) PEG, a 58–60% of the initial weights decreased in 35 days in phosphate buffer solution (pH 7.2) containing lipase enzyme. These potentially biodegradable polymers based on vegetable oil HFAs can be used as eco-friendly materials for various applications to replace the existing petroleum-based polymers currently used.

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Abbreviations

ACO:

Acrylated castor oil

ADOD:

Acrylated 7,10-dihydroxy-8(E)-octadecenoic acid

AESO:

Acrylated epoxidized soybean oil

CO:

Castor oil

DMPA:

2,2-Dimethoxy-2-phenylacetophenone

DOD:

7,10-Dihydroxy-8(E)-octadecenoic acid

HFA:

Hydroxyfatty acid

PCLDA:

Poly(ε-caprolactone) diacrylate

PEGDA:

Poly(ethylene glycol) diacrylate

UV:

Ultraviolet

References

  1. Zimmerman DC (1966) A new product of linoleic acid oxidation by a flaxseed enzyme. Biochem Biophys Res Commun 23:398–402

    Article  CAS  Google Scholar 

  2. Chang I-A, Kim I-H, Kang S-C, Hou CT, Kim H-R (2007) Production of 7, 10-dihydroxy-8(E)-octadecenoic acid from triolein via lipase induction by Pseudomonas aeruginosa PR3. Appl Microbiol Biotechnol 74:301–306

    Article  CAS  Google Scholar 

  3. Bae J-H, Suh M-J, Kim BS, Hou CT, Lee I-J, Kim I-H, Kim H-R (2010) Optimal production of 7,10-dihydroxy-8(E)-hexadecenoic acid from palmitoleic acid by Pseudomonas aeruginosa. New Biotechnol. doi:10.1016/j.nbt.2009.11.005

  4. Hou CT, Forman RJ III (2000) Growth inhibition of plant pathogenic fungi by hydroxy fatty acids. J Ind Microbiol 24:275–276

    Article  CAS  Google Scholar 

  5. Kato T, Yamaguchi Y, Abe N, Uyehara T, Nakai T, Yamanaka S, Harada N (1984) Unsaturated hydroxy fatty acids, the self-defensive substances in rice plant against blast disease. Chem Lett 25:409–412

    Article  Google Scholar 

  6. Masui H, Kondo T, Kojima M (1989) An antifungal compound, 9, 12, 13-trihydroxy-(E)-octadecenoic acid, from Colocasia antiquorum inoculated with Ceratocytis fimbriata. Phytochemistry 28:2613–2615

    Article  CAS  Google Scholar 

  7. Dumont M-J (2010) Polyurethanes plastic sheets and foams synthesized from aromatic triols. Ph.D. Dissertation, University of Alberta

  8. Hou CT (2009) Biotechnology for fats and oils: new oxygenated fatty acids. New Biotechnol 26:2–10

    Article  CAS  Google Scholar 

  9. Kim H-R, Gardner HW, Hou CT (2000) 10(S)-hydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of oleic acid to 7, 10-dihydroxy-8(E)-octadecenoic acid. J Am Oil Chem Soc 77:95–99

    Article  CAS  Google Scholar 

  10. Hou CT, Hosokawa M (2005) Production of value-added industrial products from vegetable oils: oxygenated fatty acids. In: Hou CT (ed) Handbook of industrial biocatalysis. CRC Press, Boca Raton, FL, USA, pp 7-1–7-25

    Chapter  Google Scholar 

  11. Shogren RL, Petrovic Z, Liu Z, Erhan SZ (2004) Biodegradation behavior of some vegetable oil-based polymers. J Polym Environ 12:173–178

    Article  CAS  Google Scholar 

  12. Petrovic ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:109–155

    Article  CAS  Google Scholar 

  13. Campanella A, Bonnaillie LM, Wool RP (2009) Polyurethane foams from soyoil-based polyols. J Appl Polym Sci 112:2567–2578

    Article  CAS  Google Scholar 

  14. Bonnaillie LM, Wool RP (2007) Thermosetting foam with a high bio-based content from acrylated epoxidized soybean oil and carbon dioxide. J Appl Polym Sci 105:1042–1052

    Article  CAS  Google Scholar 

  15. Can E, Wool RP, Küsefoglu S (2006) Soybean and castor oil based monomers: synthesis and copolymerization with styrene. J Appl Polym Sci 102:2433–2447

    Article  CAS  Google Scholar 

  16. Li F, Hasjim J, Larock RC (2003) Synthesis, structure, and thermophysical and mechanical properties of new polymers prepared by the cationic copolymerization of corn oil, styrene, and divinylbenzene. J Appl Polym Sci 90:1830–1838

    Article  CAS  Google Scholar 

  17. Kim HM, Kim H-R, Kim BS (2010) Soybean oil-based photo-crosslinked polymer networks. J. Polym Environ. doi:10.1007/s10924-010-0174-3

  18. Kim BS, Hrkach JS, Langer R (2000) Biodegradable photo-crosslinked poly(ether-ester) networks for lubricious coatings. Biomaterials 21:259–265

    Article  CAS  Google Scholar 

  19. Lee K-S, Kim DS, Kim BS (2007) Biodegradable molecularly imprinted polymers based on poly(ε-caprolactone). Biotechnol Bioprocess Eng 12:152–156

    Article  CAS  Google Scholar 

  20. Nelson JS, Applewhite TH (1966) Castor-based derivatives: synthesis of some acrylate esters. J Am Oil Chem Soc 43:542–545

    Article  CAS  Google Scholar 

  21. Kim BS, Hrkach JS, Langer R (2000) Synthesis and characterization of novel degradable poly(ether-anhydride) networks. J Polym Sci Pt A Polym Chem 38:1277–1282

    Article  CAS  Google Scholar 

  22. Kawai F (1994) Biodegradation of polyethers and polyacrylate. In: Doi Y, Fukuda K (ed) Biodegradable plastics and polymers. Elsevier, pp 24–38

  23. Wu S, Rong M, Zhang M, Hu J (2007) Mechanical performance and biodegradability of the foams derived from soybean oil resin. Acta Polym Sin 10:993–998

    Google Scholar 

  24. Rong MZ, Zhang MQ, Wu SP, Wang HJ, Czigany T (2007) Ecomaterials-foam plastics synthesized from plant oil-based resins. Mat Sci Forum 539–543:2311–2316

    Article  Google Scholar 

  25. Wang HJ, Rong MZ, Zhang MQ, Hu J, Chen HW, Czigany T (2008) Biodegradable foam plastics based on castor oil. Biomacromolecules 9:615–623

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by grant No. 2009-0083983 from the Basic Research Program of the National Research Foundation and by the Ministry of Knowledge Economy (MKE) and Korea Institute for Advancement in Technology (KIAT) through the Workforce Development Program in Strategic Technology.

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Authors and Affiliations

  1. Department of Chemical Engineering, Chungbuk National University, Cheongju, Chungbuk, 361-763, Republic of Korea

    Han-Min Kim & Beom Soo Kim

  2. Department of Animal Science and Biotechnology, Kyungpook National University, Daegu, 702-701, Republic of Korea

    Hak-Ryul Kim

  3. National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, Peoria, IL, 61604, USA

    Ching T. Hou

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  1. Han-Min Kim
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  2. Hak-Ryul Kim
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  3. Ching T. Hou
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  4. Beom Soo Kim
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Correspondence to Beom Soo Kim.

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Kim, HM., Kim, HR., Hou, C.T. et al. Biodegradable Photo-Crosslinked Thin Polymer Networks Based on Vegetable Oil Hydroxy Fatty Acids. J Am Oil Chem Soc 87, 1451–1459 (2010). https://doi.org/10.1007/s11746-010-1634-6

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  • DOI: https://doi.org/10.1007/s11746-010-1634-6

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