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Iranian Polymer Journal

, Volume 27, Issue 6, pp 405–411 | Cite as

Soybean oil-based thermoset reinforced with rosin-based monomer

  • Haibo Zhang
  • Yanping Yang
  • Minggui Shen
  • Shibin Shang
  • Jie Song
  • Jianxin Jiang
  • Zhanqian Song
Original Research
  • 26 Downloads

Abstract

A full bio-based cured resin was synthesized by copolymerization of acrylated-epoxidized soybean oil (AESO) and 2-acrylamidoethyl dehydroabietic acid (DHA-HEMAA). The rigid rosin-based monomer 2-acrylamidoethyl dehydroabietic acid was first prepared from dehydroabietic acid and N-hydroxyethylacrylamide, which was characterized by nuclear magnetic resonance and Fourier transform infrared (FTIR) spectrometry techniques. The cured resin was then synthesized and characterized by FTIR spectroscopy, differential scanning calorimetry, dynamic thermomechanical analysis, and thermogravimetric analysis, as well as using a Kruss tensiometer and a universal testing machine. The results indicated that the resin cured with rosin-based monomer exhibited excellent thermomechanical properties. The crosslink density and thermal stability of cured samples containing DHA-HEMAA at molar ratio between 10 and 30% were higher than those of AESO/DHA-HEMAA0 sample. With increasing DHA-HEMAA content, the glass transition temperature (Tg), elongation-at-break, and tensile strength of samples increased, in the stated order, from 16 to 38 °C, from 24 to 45.8%, and from 1.7 to 6.5 MPa. Due to DHA-HEMAA with a hydrophenanthrene structure, the θ values increased with the increase of DHA-HEMAA molar ratios. The full bio-based rosin thermosetting resins may have great potentials in practical application fields, such as coating, adhesive, and packaging materials.

Keywords

Bio-based cured resin Mechanical properties Rosin-based monomer Thermal stability Radical copolymerization 

Notes

Acknowledgements

This work was financially supported by the National Nature Science Foundation of China (Project no. 31470597), Discipline group construction project of CAF-ICIFP (LHSXKQ1), and Central Special Foundation for Basic Research in the Public Interest of the Chinese Academic of Forestry (CAFYBB2016QB014).

Supplementary material

13726_2018_618_MOESM1_ESM.docx (214 kb)
Supplementary material 1 (DOCX 214 KB)

References

  1. 1.
    Halden RU (2010) Plastics and health risks. Annu Rev Public Health 31:179–194CrossRefGoogle Scholar
  2. 2.
    Zhang C, Garrison TF, Madbouly SA, Kessler MR (2017) Recent advances in vegetable oil-based polymers and their composites. Prog Polym Sci 71:91–143CrossRefGoogle Scholar
  3. 3.
    Hillmyer MA (2008) Polymers from renewable resources: a perspective for a special issue of polymer reviews. Polym Rev 48:1–10CrossRefGoogle Scholar
  4. 4.
    Yao K, Tang C (2013) Controlled polymerization of next-generation renewable monomers and beyond. Macromolecules 46:1689–1712CrossRefGoogle Scholar
  5. 5.
    Yuan L, Wang Z, Trenor NM, Tang C (2015) Robust amidation transformation of plant oils into fatty derivatives for sustainable monomers and polymers. Macromolecules 48:1320–1328CrossRefGoogle Scholar
  6. 6.
    Wang Z, Yuan L, Ganewatta MS, Lamm ME, Rahman MA (2017) Plant oil-derived epoxy polymers toward sustainable biobased thermosets. Macromol Rapid Commun 38:1700009CrossRefGoogle Scholar
  7. 7.
    Yuan L, Wang Z, Trenor NM, Tang C (2016) Amidation of triglycerides by amino alcohols and their impact on plant oil-derived polymers. Polym Chem 7:2790–2798CrossRefGoogle Scholar
  8. 8.
    Can E, Wool RP, Küsefoğlu S (2006) Soybean- and castor-oil-based thermosetting polymers: mechanical properties. J Appl Polym Sci 102:1497–1504CrossRefGoogle Scholar
  9. 9.
    Uysal N, Acik G, Tasdelen MA (2017) Soybean oil based thermoset networks via photoinduced CuAAC click chemistry. Polym Int 66:999–1004CrossRefGoogle Scholar
  10. 10.
    Thakur VK, Thakur MK, Raghavan P, Kessler MR (2014) Progress in green polymer composites from lignin for multifunctional applications: a review. ACS Sustain Chem Eng 2:1072–1092CrossRefGoogle Scholar
  11. 11.
    Laurent F, Houria K, Mylène S, Olivia G, Christine JD, Vincent L, Jean-Jacques R (2013) The use of renewable feedstock in UV-curable materials—a new age for polymers and green chemistry. Prog Polym Sci 38:932–962CrossRefGoogle Scholar
  12. 12.
    Henna P, Larock RC (2009) Novel thermosets obtained by the ring-opening metathesis polymerization of a functionalized vegetable oil and dicyclopentadiene. J Appl Polym Sci 112:1788–1797CrossRefGoogle Scholar
  13. 13.
    Vendamme R, Schüwer N, Eevers W (2014) Recent synthetic approaches and emerging bio-inspired strategies for the development of sustainable pressure-sensitive adhesives derived from renewable building blocks. J Appl Polym Sci 131:8379–8394CrossRefGoogle Scholar
  14. 14.
    Russo D, Dassisti M, Lawlor V, Olabi AG (2012) State of the art of biofuels from pure plant oil. Renew Sustain Energy Rev 16:4056–4070CrossRefGoogle Scholar
  15. 15.
    Lligadas G, Ronda JC, Galia M, Cádiz V (2010) Plant oils as platform chemicals for polyurethane synthesis: current state-of-the-art. Biomacromolecules 11:2825–2835CrossRefGoogle Scholar
  16. 16.
    Petrović ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:109–155CrossRefGoogle Scholar
  17. 17.
    Rangarajan B, Havey A, Grulke EA, Culnan PD (1995) Kinetic parameters of a two-phase model for in situ epoxidation of soybean oil. J Am Oil Chem Soc 72:1161–1169CrossRefGoogle Scholar
  18. 18.
    Sylvain C, Myriam D, Gilles B, Cédric L, Rémi A, Bernard B (2012) Synthesis of new polyester polyols from epoxidized vegetable oils and biobased acids. Eur J Lipid Sci Technol 114:1447–1459CrossRefGoogle Scholar
  19. 19.
    Guo A, Demydov D, Wei Z, Petrovic ZS (2002) Polyols and polyurethanes from hydroformylation of soybean oil. J Polym Environ 10:49–52CrossRefGoogle Scholar
  20. 20.
    Das B, Konwar U, Mandal M, Karak N (2013) Sunflower oil based biodegradable hyperbranched polyurethane as a thin film material. Ind Crops Prod 44:396–404CrossRefGoogle Scholar
  21. 21.
    Ionescu M, Radojčić D, Wan X, Petrović ZS, Upshaw TA (2015) Functionalized vegetable oils as precursors for polymers by thiol-ene reaction. Eur Polym J 67:439–448CrossRefGoogle Scholar
  22. 22.
    La SJ, Wool RP (2002) The effect of fatty acid composition on the acrylation kinetics of epoxidized triacylglycerols. J Am Oil Chem Soc 79:59–63CrossRefGoogle Scholar
  23. 23.
    Pelletier H, Belgacem N, Gandini A (2006) Acrylated vegetable oils as photocrosslinkable materials. J Appl Polym Sci 99:3218–3221CrossRefGoogle Scholar
  24. 24.
    Ma S, Li T, Liu X, Zhu J (2016) Research progress on bio-based thermosetting resins. Polym Int 65:164–173CrossRefGoogle Scholar
  25. 25.
    Kolot V, Grinberg S (2010) Vernonia oil–based acrylate and methacrylate polymers and interpenetrating polymer networks with epoxy resins. J Appl Polym Sci 91:3835–3843CrossRefGoogle Scholar
  26. 26.
    Kun L, Samy M, Michael K (2015) Biorenewable thermosetting copolymer based on soybean oil and eugenol. Eur Polym J 69:16–28CrossRefGoogle Scholar
  27. 27.
    Wilbon PA, Chu F Tang C (2013) Progress in renewable polymers from natural terpenes, terpenoids, and rosin. Macromol Rapid Commun 34:8–37CrossRefGoogle Scholar
  28. 28.
    El-Ghazawy RA, El-Saeed AM, Al-Shafey HI, Abdul-Raheim ARM, El-Sockary MA (2015) Rosin based epoxy coating: synthesis, identification and characterization. Eur Polym J 69:403–415CrossRefGoogle Scholar
  29. 29.
    Wang H, Liu X, Liu B, Zhang J, Xian M (2009) Synthesis of rosin-based flexible anhydride-type curing agents and properties of the cured epoxy. Polym Int 58:1435–1441CrossRefGoogle Scholar
  30. 30.
    Ma Q, Liu X, Zhang R, Zhu J, Jiang Y (2013) Synthesis and properties of full bio-based thermosetting resins from rosin acid and soybean oil: the role of rosin acid derivatives. Green Chem 15:1300–1310CrossRefGoogle Scholar
  31. 31.
    Yang Y, Shen M, Huang X, Zhang H, Shang S, Song J (2017) Synthesis and performance of a thermosetting resin: acrylated epoxidized soybean oil curing with a rosin-based acrylamide. J Appl Polym Sci 134:44545Google Scholar
  32. 32.
    Zhang H, Huang X, Jiang J, Shang S, Song Z (2017) Hydrogels with high mechanical strength cross-linked by a rosin-based crosslinking agent. RSC Adv 7:42541–42548CrossRefGoogle Scholar
  33. 33.
    Liu X, Xin W, Zhang J (2009) Rosin-based acid anhydrides as alternatives to petrochemical curing agents. Green Chem 11:1018–1025CrossRefGoogle Scholar
  34. 34.
    Tao Z, Yang S, Chen J, Fan L (2007) Synthesis and characterization of imide ring and siloxane-containing cycloaliphatic epoxy resins. Eur Polym J 43:1470–1479CrossRefGoogle Scholar
  35. 35.
    Yang X, Li S, Xia J, Song J, Huang K, Li M (2015) Novel renewable resource-based UV-curable copolymers derived from myrcene and tung oil: preparation, characterization and properties. Ind Crops Prod 63:17–25CrossRefGoogle Scholar

Copyright information

© Iran Polymer and Petrochemical Institute 2018

Authors and Affiliations

  1. 1.Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab. for Biomass Chemical Utilization; Key and Open Lab. of Forest Chemical Engineering, SFA; Key Lab. of Biomass Energy and MaterialNanjingChina
  2. 2.College of Materials Science and Technology, Engineering Research Center of Forestry Biomass Material and Bioenergy, Ministry of EducationBeijing Forestry UniversityBeijingChina
  3. 3.Department of Chemistry and BiochemistryUniversity of Michigan-FlintFlintUSA

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