745
Views
18
CrossRef citations to date
0
Altmetric
Original Articles

Epoxidation of Methanol-Soluble Kraft Lignin for Lignin-Derived Epoxy Resin and Its Usage in the Preparation of Biopolyester

, &

REFERENCES

  • Auvergne, R.; Caillol, S.; David, G.; Boutevin, B.; Pascault, J.P. Biobased thermosetting epoxy: present and future. Chemical Reviews 2013, 114, 1082–1115.
  • Huo, S.P.; Wu, G.M.; Chen, J.; Liu, G.F.; Kong, Z.W. Curing kinetics of lignin and cardanol based novolac epoxy resin with methyl tetrahydrophthalic anhydride. Thermochimica Acta 2014, 587, 18–23.
  • Li, K.; Wang, K.; Zhan, M.S.; Xu, W. The change of thermal–mechanical properties and chemical structure of ambient cured DGEBA/TEPA under accelerated thermo-oxidative aging. Polymer Degradation and Stability 2013, 98, 2340–2346.
  • Bogdal, D.; Gorczyk, J.; Kwasek, B. Microwave-assisted synthesis of solid epoxy resins: study of molecular weight by GPC and MALDI-TOF/MS. ACS Sustainable Chemistry & Engineering 2016, 4, 3024–3031.
  • Asada, C.; Basnet, S.; Otsuka, M.; Sasaki, C.; Nakamura, Y. Epoxy resin synthesis using low molecular weight lignin separated from various lignocellulosic materials. International Journal of Biological Macromolecules 2015, 74, 413–419.
  • Aouf, C.; Lecomte, J.; Villeneuve, P.; Dubreucq, E.; Fulcrand, H. Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers. Green Chemistry 2012, 14, 2328–2336.
  • Basnet, S.; Otsuka, M.; Sasaki, C.; Asada, C.; Nakamura, Y. Functionalization of the active ingredients of Japanese green tea (Camellia sinensis) for the synthesis of bio-based epoxy resin. Industrial Crops and Products 2015, 73, 63–72.
  • Steinmetz, R.; Brown, N.G.; Allen, D.L.; Bigsby, R.M.; Ben-Jonathan, N. The environmental estrogen Bisphenol A stimulates prolactin release in vitro and in vivo. Endocrinology 1997, 138, 1780–1786.
  • Hirose, S.; Hatakeyama, T.; Hatakeyama, H. Curing and glass transition of epoxy resins from ester‐carboxylic acid derivatives of mono‐and disaccharides, and alcoholysis Lignin. Macromolecular Symposia 2005, 224, 343–354.
  • Ma, S.; Liu, X.; Jiang, Y.; Tang, Z.; Zhang, C.; Zhu, J. Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers. Green Chemistry 2013, 15, 245–254.
  • Campanella, A.; Baltanas, M.A.; Capel-Sanchez, M.C.; Campos-Martin, J.M.; Fierro, J.L.G. Soybean oil epoxidation with hydrogen peroxide using an amorphous Ti/SiO2 catalyst. Green Chemistry 2004, 6, 330–334.
  • Koike, T. Progress in development of epoxy resin systems based on wood biomass in Japan. Polymer Engineering & Science 2012, 52, 701–717.
  • Laurichesse, S.; Avérous, L. Chemical modification of lignins: towards biobased polymers. Progress in Polymer Science 2014, 39, 1266–1290.
  • Upton, B.M.; Kasko, A.M. Strategies for the conversion of lignin to high-value polymeric materials: review and perspective. Chemical Reviews 2015, 116, 2275–2306.
  • Lee, J.H.; Lee, E.Y. Biobutanediol-mediated liquefaction of empty fruit bunch saccharification residues to prepare lignin biopolyols. Bioresource Technology 2016, 208, 24–30.
  • Saito, T.; Perkins, J.H.; Jackson, D.C.; Trammel, N.E.; Hunt, M.A.; Naskar, A.K. Development of lignin-based polyurethane thermoplastics. RSC Advances 2013, 3, 21832–21840.
  • Kai, D.; Tan, M.J.; Chee, P.L.; Chua, Y.K.; Yap, Y.L.; Loh, X.J. Towards lignin-based functional materials in a sustainable world. Green Chemistry 2016, 18, 1175–1200.
  • Kim, K.H.; Yu, J.H.; Lee, E.Y. Crude glycerol-mediated liquefaction of saccharification residues of sunflower stalks for production of lignin biopolyols. Journal of Industrial and Engineering Chemistry 2016, 38, 175–180.
  • Thakur, V.K.; Thakur, M.K.; Raghavan, P.; Kessler, M. R. Progress in green polymer composites from lignin for multifunctional applications: a review. ACS Sustain. Chemical Engineering Journal 2014, 2, 1072–1092.
  • El Mansouri, N.E.; Yuan, Q.; Huang, F. Synthesis and characterization of kraft lignin-based epoxy resins. BioResources 2011, 6, 2492–2503.
  • Lora, J.H.; Glasser, W.G. Recent industrial applications of lignin: a sustainable alternative to nonrenewable materials. Journal of Polymers and the Environment 2002, 10, 39–48.
  • Sasaki, C.; Wanaka, M.; Takagi, H.; Tamura, S.; Asada, C.; Nakamura, Y. Evaluation of epoxy resins synthesized from steam-exploded bamboo lignin. Industrial Crops and Products 2013, 43, 757–761.
  • Ferdosian, F.; Yuan, Z.; Anderson, M.; Xu, C.C. Synthesis of lignin-based epoxy resins: optimization of reaction parameters using response surface methodology. RSC Advances 2014, 4, 31745–31753.
  • Kishi, H.; Fujita, A.; Miyazaki, H.; Matsuda, S.; Murakami, A. Synthesis of wood‐based epoxy resins and their mechanical and adhesive properties. Journal of Applied Polymer Science 2006, 102, 2285–2292.
  • Saito, T.; Perkins, J.H.; Vautard, F.; Meyer, H.M.; Messman, J.M.; Tolnai, B.; Naskar, A.K. Methanol fractionation of softwood kraft lignin: Impact on the lignin properties. ChemSusChem 2014, 7, 221–228.
  • Qin, J.; Woloctt, M.; Zhang, J. Use of polycarboxylic acid derived from partially depolymerized lignin as a curing agent for epoxy application. ACS Sustain. Chemical Engineering Journal 2013, 2, 188–193.
  • Thielemans, W.; Wool, R.P. Lignin esters for use in unsaturated thermosets: Lignin modification and solubility modeling. Biomacromolecules 2005, 6, 1895–1905.
  • Xin, J.; Li, M.; Li, R.; Wolcott, M.P.; Zhang, J. Green Epoxy Resin System Based on Lignin and Tung Oil and Its Application in Epoxy Asphalt. ACS Sustainable Chemistry & Engineering 2016, 4, 2754–2761.
  • Pan, H.; Sun, G.; Zhao, T. Synthesis and characterization of aminated lignin. International Journal of Biological Macromolecules 2013, 59, 221–226.
  • Garea, S.A.; Corbu, A.C.; Deleanu, C.; Iovu, H. Determination of the epoxide equivalent weight (EEW) of epoxy resins with different chemical structure and functionality using GPC and 1 H-NMR. Polymer Testing 2006, 25, 107–113.
  • Pramanik, M.; Mendon, S.K.; Rawlins, J.W. Determination of epoxy equivalent weight of glycidyl ether based epoxides via near infrared spectroscopy. Polymer Testing 2012, 31, 716–721.
  • Zhao, B.; Chen, G.; Liu, Y.U.; Hu, K.; Wu, R. Synthesis of lignin base epoxy resin and its characterization. Journal of Materials Science Letters 2001, 20, 859–862.
  • Fischer, R.F. Polyesters from expoxides and anhydrides. Journal of Polymer Science 1960, 44, 155–172.
  • Sun, G.; Sun, H.; Liu, Y.; Zhao, B.; Zhu, N.; Hu, K. Comparative study on the curing kinetics and mechanism of a lignin-based-epoxy/anhydride resin system. Polymer 2007, 48, 330–337.
  • Liu, X.; Xin, W.; Zhang, J. Rosin-based acid anhydrides as alternatives to petrochemical curing agents. Green Chemistry 2009, 11, 1018–1025.
  • Asada, C.; Sasaki, C.; Uto, Y.; Sakafuji, J.; Nakamura, Y. Effect of steam explosion pretreatment with ultra-high temperature and pressure on effective utilization of softwood biomass. Biochemical Engineering Journal 2012, 60, 25–29.
  • Chen, H.Z.; Li, Z.Y.; Liu, X.Y.; Tian, Y.M.; Yang, L.; Wang, Z.C. Depolymerization of renewable resources-lignin by sodium hydroxide as a catalyst and its applications to epoxy resin. Journal of Applied Polymer Science 2015, 132, 42176.
  • Park, S.J.; Cho, K.S. Filler–elastomer interactions: influence of silane coupling agent on crosslink density and thermal stability of silica/rubber composites. Journal of Colloid and Interface Science 2003, 267, 86–91.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.