Vanillin-based polymers: IV. Hydrovanilloin epoxy resins
Corresponding Author
Ananda S. Amarasekara
Department of Chemistry, Prairie View A&M University, Prairie View, Texas, 77446 USA
Correspondence to: A. S. Amarasekara (E-mail: [email protected])Search for more papers by this authorRocio Garcia-Obergon
Department of Chemistry, Prairie View A&M University, Prairie View, Texas, 77446 USA
Search for more papers by this authorAudie K. Thompson
Department of Chemical Engineering, Prairie View A&M University, Prairie View, Texas, 77446 USA
Search for more papers by this authorCorresponding Author
Ananda S. Amarasekara
Department of Chemistry, Prairie View A&M University, Prairie View, Texas, 77446 USA
Correspondence to: A. S. Amarasekara (E-mail: [email protected])Search for more papers by this authorRocio Garcia-Obergon
Department of Chemistry, Prairie View A&M University, Prairie View, Texas, 77446 USA
Search for more papers by this authorAudie K. Thompson
Department of Chemical Engineering, Prairie View A&M University, Prairie View, Texas, 77446 USA
Search for more papers by this authorABSTRACT
In this study, hydrovanilloin synthesized by electrochemical dimerization of vanillin has been used as a renewable substitute for bisphenol A for the preparation of epoxy resins. The reaction of the disodium salt of hydrovanilloin:epichlorohydrin 1:2 mol ratio at 80°C for 30 min in water gave a hydrovanilloin – diglycidyl ether phenoxy resin. This hard thermoplastic resin showed Tg of 135°C and stable up to 255°C in air. On the other hand, the disodium salt of hydrovanilloin:epichlorohydrin 1:4 mol ratio at 80°C for 30 min in water gives a curable oligomer of hydrovanilloin – diglycidyl ether with 2.1 repeating units. This oligomer could be cured with aliphatic diamines: 1,2-diaminoethane, 1,4-diaminobutane, 1,6-diaminohexane, and isophorone diamine to give hard epoxy resins with Tg values of 116, 118, 149 and 146°C, respectively. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47000.
Supporting Information
| Filename | Description |
|---|---|
| app47000-sup-0001-supinfo.pdfPDF document, 52.8 KB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1Kobayashi, S. Struct. Chem. 2017, 28, 461.
- 2Zhu, Y.; Romain, C.; Williams, C. K. Nature. 2016, 540, 354.
- 3 V. Mittal, Ed. Renewable Polymers; Salem, MA: Scrivener-Wiley, 2012.
- 4Jiang, Y.; Ding, D.; Zhao, S.; Zhu, H.; Kenttamaa, H. I.; Abu-Omar, M. M. Green Chem. 2018, 20, 1131.
- 5Montero De Espinosa, L.; Meier, M. A. R. Eur. Polym. J. 2011, 47, 837.
- 6Sharma, V.; Kundu, P. P. Prog. Polym. Sci. 2006, 31, 983.
- 7Pang, X.; Zhuang, X.; Tang, Z.; Chen, X. Biotechnol. J. 2010, 5, 1125.
- 8Arora, P. B.; Patel, H. S.; Patel, S. R. Eur. Polym. J. 1987, 23, 307.
- 9Gandini, A. Polym. Chem. 2010, 1, 245.
- 10Amarasekara, A. S.; Razzaq, A.; Bonham, P. ISRN Polym. Sci. 2013, 2013, 645169.
- 11Amarasekara, A. S.; Hawkins, S. A. Eur. Polym. J. 2011, 47, 2451.
- 12Mazière, A.; Prinsen, P.; García, A.; Luque, R.; Len, C. Biofuel. Bioproduct. Biorefin. 2017, 11, 908.
- 13Fache, M.; Boutevin, B.; Caillol, S. Eur. Polym. J. 2015, 68, 488.
- 14Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Green Chem. 2014, 16, 1987.
- 15Kayser, L. V.; Hartigan, E. M.; Arndtsen, B. A. ACS Sustain. Chem. Eng. 2016, 4, 6263.
- 16Barbara, I.; Flourat, A. L.; Allais, F. Eur. Polym. J. 2015, 62, 236.
- 17Takeshima, H.; Satoh, K.; Kamigaito, M. Macromolecules. 2017, 50, 4206.
- 18Sinha, A. K.; Sharma, U. K.; Sharma, N. Int. J. Food Sci. Nutr. 2008, 59, 299.
- 19Araújo, J. D. P.; Grande, C. A.; Rodrigues, A. E. Chem. Eng. Res. Des. 2010, 88, 1024.
- 20Voitl, T.; Von Rohr, P. R. Ind. Eng. Chem. Res. 2010, 49, 520.
- 21Kaur, B.; Chakraborty, D. Appl. Biochem. Biotechnol. 2013, 169, 1353.
- 22Havkin-Frenkel, D.; Belanger, F. C. Biotechnology in Flavor Production; New York, NY: John-Wiley, 2009.
10.1002/9781444302493 Google Scholar
- 23Hernandez, E. D.; Bassett, A. W.; Sadler, J. M.; La Scala, J. J.; Stanzione, J. F., III. ACS Sustain. Chem. Eng. 2016, 4, 4328.
- 24Fache, M.; Viola, A.; Auvergne, R.; Boutevin, B.; Caillol, S. Eur. Polym. J. 2015, 68, 526.
- 25Harvey, B. G.; Guenthner, A. J.; Meylemans, H. A.; Haines, S. R. L.; Lamison, K. R.; Groshens, T. J.; Cambrea, L. R.; Davis, M. C.; Lai, W. W. Green Chem. 2015, 17, 1249.
- 26Nikafshar, S.; Zabihi, O.; Hamidi, S.; Moradi, Y.; Barzegar, S.; Ahmadi, M.; Naebe, M. RSC Adv. 2017, 7, 8694.
- 27Mialon, L.; Pemba, A. G.; Miller, S. A. Green Chem. 2010, 12, 1704.
- 28Amarasekara, A. S.; Ha, U.; Okorie, N. C. J. Polym. Sci. A Polym. Chem. 2018, 56, 955.
- 29Amarasekara, A. S.; Singh, T. B.; Larkin, E.; Hasan, M. A.; Fan, H.-J. Ind. Crop Prod. 2015, 65, 546.
- 30Amarasekara, A. S.; Hasan, M. A. Cat. Com. 2015, 60, 5.
- 31Amarasekara, A. S.; Green, D.; Williams, L. D. Eur. Polym. J. 2009, 45, 595.
- 32Amarasekara, A. S.; Owereh, O. S. Carbohydr. Polym. 2009, 78, 635.
- 33Amarasekara, A. S.; Razzaq, A. ISRN Polym. Sci. 2012, 532171.
- 34Amarasekara, A. S.; Wiredu, B.; Razzaq, A. Green Chem. 2012, 14, 2395.
- 35Amarasekara, A. S.; Hasan, M. A. Polym. Sci. B. 2016, 58, 307.
- 36Gorecki, S.; Bemrah, N.; Roudot, A.-C.; Marchioni, E.; Le Bizec, B.; Faivre, F.; Kadawathagedara, M.; Botton, J.; Rivière, G.; EDEN Mother−Child Cohort Study Group. Food Chem. Toxicol. 2017, 110, 333.
- 37vom Saal, F. S.; Hughes, C. Environ. Health Perspect. 2005, 113, 926.
- 38Pearl, I. A. J. Am. Chem. Soc. 1952, 74, 4260.
- 39Kumar, S.; Samal, S. K.; Mohanty, S.; Nayak, S. K. Polym.-Plastics Technol. Eng. 2018, 57, 133.
- 40Jin, F.-L.; Li, X.; Park, S.-J. J. Ind. Eng. Chem. 2015, 29, 1.
- 41Wan, J.; Gan, B.; Li, C.; Molina-Aldareguia, J.; Li, Z.; Wang, X.; Wang, D.-Y. J. Mater. Chem. A. 2015, 3, 21907.
- 42Rosu, D.; Mustata, F.; Tudorachi, N.; Musteata, V.; Rosu, L.; Varganici, C. RSC Adv. 2015, 5, 45679.
- 43Reddy Paluvai, N.; Mohanty, S.; Nayak, S. J. Reinforced Plastic. Composit. 2015, 34, 1476.
- 44Ma, S.; Liu, X.; Jiang, Y.; Fan, L.; Feng, J.; Zhu, J. Sci. China Chem. 2014, 57, 379.
- 45Mashouf Roudsari, G.; Mohanty, A. K.; Misra, M. ACS Sustain. Chem. Eng. 2014, 2, 2111.
- 46Jaillet, F.; Darroman, E.; Ratsimihety, A.; Auvergne, R.; Boutevin, B.; Caillol, S. Eur. J. Lipid Sci. Technol. 2014, 116, 63.
- 47Deng, J.; Liu, X.; Li, C.; Jiang, Y.; Zhu, J. RSC Adv. 2015, 5, 15930.
- 48Li, T.; Liu, X.; Jiang, Y.; Ma, S.; Zhu, J. Iran. Polym. J. 2016, 25, 957.
- 49Ngo, H. L.; LeCompte, K.; Hargens, L.; McEwen, A. B. Thermochim. Acta. 2000, 357, 97.
- 50Rigail-Cedeño, A.; Sung, C. S. P. Polymer. 2005, 46, 9378.
- 51Yang, G.; Rohde, B. J.; Tesefay, H.; Robertson, M. L. ACS Sustain. Chem. Eng. 2016, 4, 6524.
- 52Shibata, M.; Ohkita, T. Eur. Polym. J. 2017, 92, 165.
- 53François, C.; Pourchet, S.; Boni, G.; Rautiainen, S.; Samec, J.; Fournier, L.; Robert, C.; Thomas, C. M.; Fontaine, S.; Gaillard, Y. C. R. Chim. 2017, 20, 1006.
- 54Zhang, J.; Xu, Y.; Huang, P. Express Polym. Lett. 2009, 3, 534.
Citing Literature
