Abstract
In this study, a new type of bio-based azobenzene-containing benzoxazine (Bza) was synthesized using p-aminoazobenzene, paraformaldehyde, and cardanol the raw materials, and the resulting Bza was mixed with bio-based epoxy soybean oil (ESO) in different composition ratios in the presence of adipic acid as a reaction curing agent, affording a bio-based thermosetting composite thermosets. The chemical structure of the synthesized Bza was characterized by Fourier transform infrared spectroscopy and 1H nuclear magnetic resonance spectroscopy. The thermal curing behavior in the absence of any catalyst was investigated by differential scanning calorimetry, indicating that the synthesized Bza exhibits certain liquid crystalline characteristics during heating. The existence of liquid crystal state was further confirmed by the polarizing microscope studies. The mechanical and thermal properties of the composite thermosets with different proportions of Bza were studied. The results show that the addition of increasing amount of Bza to ESO improved its performance to a certain extent; however, further addition beyond a certain range deteriorated the performance. Attributing to excellent processability and high performance of soybean oil-based thermosetting materials and photochromism of azobenzene compounds, the resulting composite materials endowing the characteristics of their components will have a wide range of applications in many fields.
Similar content being viewed by others
References
Liu W, Xie T, Qiu R (2017) Biobased Thermosets Prepared from Rigid Isosorbide and Flexible Soybean Oil Derivatives. ACS Sustain Chem Eng 5(1):774–783
Li YT, Yang LT, Zhang H et al (2017) Synthesis and curing performance of a novel bio-based epoxy Monomer from soybean oil. Eur J Lipid Sci Technol 119(8):1438–7697
Dai JY, Yang SM, Teng N et al (2018) Synthesis of Eugenol-Based Silicon-Containing Benzoxazines and Their Applications as Bio-Based Organic Coatings. Coatings 8(3):2079–6412
Gandini A (2008) Polymers from renewable resources: A challenge for The future of macromolecular materials. Macromolecules 41(24):9491–9504
Mosiewick MA, Aranguren MI (2013) Short Review on Novel Biocomposites Based on Plant Oil Precursors. Eur Polym J 49(6):1243–1256
Meier MAR, Metzger JO, Schubert US (2007) Plant Oil Renewable Resources as Green Alternatives in Polymer Science. Chem Soc Rev 36(11):1788–1802
Díez-Pascual AM, Díez-Vicente AL (2014) Epoxidized Soybean Oil/ZnO Biocomposites for Soft Tissue Applications: Preparation and Characterization. ACS Appl Mater Interfaces 6(19):17277–17288
Raqueza JM, Deleglisea M, Lacrampea MF, Krawczaka P (2010) Thermosetting (Bio) materials Derived from Renewable Resources: A Critical Review. Prog Polym Sci 35(4): 487−509
Trin K, Hunt AJ, Nontipa S (2018) Development of hyperbranched crosslinkers from bio-derived platform molecules for the synthesis of epoxidised soybean oil based thermosets. RSC Adv 8(65):37267–37276
Kumar S, Mohanty S, Nayak SK (2020) Nanocomposites of epoxidized soybean oil (ESO)-based epoxy (DGEBA) blends and clay platelets: cured with methylhexahydrophthalic anhydride crosslinker. J Macromol Sci, Part A 57(9):1060–1325
Samper M, Fombuena V, Boronat T et al (2012) Thermal and mechanical characterization of epoxy resins (ELO and ESO) cured with anhydrides. J Am Oil Chem Soc 89(8):1521–1528
Ammar S, Iling AWM, Ramesh K et al (2020a) Development of fully organic coating system modified with epoxidized soybean oil with superior corrosion protection performance. Prog Org Coat 140:0300–9440
Sushanta KS, Smita M, Sanjay KN (2015) Synthesis and Characterization of Bio-based Epoxy Blends from Renewable Resource Based Epoxidized Soybean Oil as Reactive Diluent. Chin J Polym Sci 33(1):137–152
Narita K, Chahinez A, Hélène F et al (2019) Bio-based flexible epoxy foam synthesized from epoxidized soybean oil andepoxidized mangosteen tannin. Ind Crops Prod 128:0926–6690
Chow WS, Tan SG, Ahmad Z et al (2014) Biodegradability of Epoxidized Soybean Oil Based Thermosets in Compost Soil Environment. J Polym Environ 22(1):140–147
Tan SG, Chow WS (2011) Curing characteristics and thermal properties of epoxidized soybean oil based thermosetting resin. J Am Oil Chem Soc 88(7):915–923
Ammar S, Iling AWM, Ramesh K et al (2020b) Development of fully organic coating system modified with epoxidized soybeanoil with superior corrosion protection performance. Prog Org Coat 140:0300–9440
Espinoza-Perez JD, Nerenz BA, Haagenson DM et al (2011) Comparison of curing agents for epoxidized vegetable oils applied to composites. Polym Compos 32(11):1806–1816
Tan SG, Ahmad Z, Chow WS (2012) Relationships of cure kinetics and processing for epoxidized soybean oil bio-thermoset. Ind Crops Prod 43:378–385
Sudheer K, Sushanta KS, Smita M et al (2017) Epoxidized Soybean Oil-Based Epoxy Blend Cured with Anhydride-Based Cross-Linker: Thermal and Mechanical Characterization. Ind Eng Chem Res 56(3):687–698
Tan K, Luo J, Zhu Y et al (2019) Tannic acid functionalized UV-curable carbon nanotube: Effective reinforcement of acrylated epoxidized soybean oil coating. Prog Org Coat 130:214–220
Bach QV, Vu CM, Vu HT et al (2019) Epoxidized soybean oil grafted with CTBN as a novel toughener for improving the fracture toughness and mechanical properties of epoxy resin. Polym J 0032−3869
Zhan G, Tang X, Yu Y et al (2011) Biobased Cyanate Ester Composites with Epoxidized Soybean Oil and in Situ Generated Nano-Silica. Polym Eng Sci 51(3):426–433
Zhang J, Hu S, Zhan G et al (2013) Biobased Nanocomposites from Clay Modified Blend of Epoxidized Soybean Oil and Cyanate Ester Resin. Prog Org Coat 76(11):1683–1690
Lakho DA, Yao DG, Cho KH et al (2017) Study of the Curing Kinetics toward Development of Fast-Curing Epoxy Resins. Polym-Plast Technol Eng 56(2):161–170
Zhang K, Liu YQ, Han MC et al (2020) Smart and sustainable design of latent catalyst-containing benzoxazine-bio-resins and application studies. Green Chem 22(4):1209–1219
Yan HQ, Sun C, Fang ZP et al (2016) Synthesis of an intrinsically flame retardant bio-based benzoxazine resin. Polymer 97:418–427
Zhang K, Han M, Liu Y et al (2019) Design and Synthesis of Bio-Based High-Performance Trioxazine Benzoxazine Resin via Natural Renewable Resources. ACS Sustain Chem Eng 7(10):9399–9407
Li SL, Zhao CX, Wang YN et al (2018) Synthesis and electrochemical properties of electroactive aniline-dimer-based benzoxazines for advanced corrosion-resistant coatings. J Mater Sci 53(10):7344–7356
Hao B, Han L, Liu Y, Zhang K et al (2020) An apigenin-based bio-benzoxazine with three polymerizable functionalities: sustainable synthesis, thermal latent polymerization, and excellent thermal properties of its thermosets. Polym Chem 11(36): 5800−5809
Kiskan B, Dogan F, Durmaz YY et al (2009) Synthesis, characterization and thermally-activated curing of azobenzene-containing benzoxazines. Des Monomers Polym 11(5):473–482
Kiskan B, Demirel AL, Kamer O et al (2008) Synthesis and characterization of nanomagnetite thermosets based on benzoxazines. J Polym Sci, Part A: Polym Chem 46(20):6780–6788
Mohamed MG, Hsiao CH, Hsu KC et al (2015) Supramolecular functionalized polybenzoxazines from azobenzene carboxylic acid/azobenzene pyridine complexes: synthesis, surface properties, and specific interactions. RSC Adv 5(17):12763–12772
EL-Mahdy AF, Lin FW, Su WH, Chen T, Kuo SW et al (2019) Photoresponsive Azobenzene Materials Based on Pyridine-Functionalized Benzoxazines as Surface Relief Gratings. ACS Appl Polym Mater 2(2): 791−804
Lou C, Zhang R, Zhou CL et al (2019) Facile fabrication of epoxy/polybenzoxazine based superhydrophobic coating with enhanced corrosion resistance and high thermal stability. Colloids Surf A: Phys Eng Asp 562:8–15
Li XD, Xia YQ, Xu WL et al (2012) The curing procedure for Abenzoxazine-cyanate-epoxy system and the properties of the terpolymer. Polym Chem 3(6):1629–1633
Hao B, Yang R, Zhang K (2020) A naringenin-based benzoxazine with an intramolecular hydrogen bond as both a thermal latent polymerization additive and property modifier for epoxy resins. RSC Adv 10(43):25629–25638
Kimura H, Matsumoto A, Ohtsuk K (2008) Studies on new type of phenolic resin−Curing reaction of bisphenol-A-based benzoxazine with epoxy resin using latent curing agent and the properties of the cured resin. J Appl Polym Sci 109(2):1248–1256
Thirukumaran P, Parveen AS, Sarojadevi M (2014) Synthesis and Copolymerization of fully biobased benzoxazines from renewable resources. ACS Sustain Chem Eng 2(12):2790–2801
Vitae MFA, Vitae BBA, Vitae SCA (2015) Vanillin, a key-intermediate of biobased polymers. Eur Polym J 68:488–502
Alev T, Gerard L, Ronda JC et al (2016) Castor oil-derived benzoxazines: Synthesis, self-metathesis and properties of the resulting thermosets. Eur Polym J 75:56–66
Zhang CX, Ling H, Gu Y (2011) Curing characteristics of cardanolbenzoxazine. Polym Mater Sci Eng 27(5):92–95
Kurihara M, Hirooka A, Kume S et al (2002) Redox-conjugated reversible isomerization ferrocenylazobenzene with a single green light. J Am Chem Soc 124(30):8800–8801
Dinda S, Patwardhan AV, Goud VV et al (2008) Epoxidation of Cottonseed Oil by Aqueous Hydrogen Peroxide Catalysed by Liquid Inorganic Acids. Bioresour Technol 99(9):3737–3744
Ma SQ, Jiang YH, Liu XQ et al (2014) Bio-based tetrafunctional crosslink agent from gallic acid and its enhanced soybean oil-based UV-cured coatings with high performance. RSC Adv 4(44):23036–23042
Lin CH, Shih YS, Wang MW et al (2014) Pyridinyl-containing benzoxazine: Unusual curing behaviors with epoxy resins. Polymer 55(7):1666–1673
Liu H, Wang XD, Wu DZ (2015) Preparation, isothermal kinetics, and performance of a novel epoxy thermosetting system based on phosphazene-cyclomatrix network for halogen-free flame retardancy and high thermal stability. Thermochim Acta 607:60–73
Ma SQ, Liu XQ, Jiang YH et al (2013) Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers. Green Chem 15(1):245–254
Zeng RT, Wu Y, Li YD et al (2017) Curing behavior of epoxidized soybean oil with biobased dicarboxylic acids. Polym Test 57:281–287
Acknowledgements
This work was supported by the National Natural Science Foundation of China (51703191), the Science and Technology Plan Project in Sichuan Province (2019YFG0242).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interests
The author(s) declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Wu, J., Zhao, C., Li, Y. et al. Properties of bio-based thermosetting composites synthesized from epoxidized soybean oil and azo-cardanol benzoxazine. J Polym Res 28, 77 (2021). https://doi.org/10.1007/s10965-021-02442-z
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-021-02442-z