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Synthesis of a novel cardanol-based compound and environmentally sustainable production of phenolic foam

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Abstract

A novel phosphorus-containing cardanol (PCC) derived from cardanol—a renewable meta-substituted phenol and harmful by-product of the cashew industry—in combination with 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) was used to produce bio-based phenolic foams (PFs). The properties of the PFs were then characterized in detail. The PCC was fully characterized by using Fourier transform infrared spectroscopy (FTIR) and proton nuclear magnetic resonance (1H NMR), while the thermal degradation was studied and monitored by thermogravimetry coupled to FTIR (TGA/FTIR) and TGA coupled with mass spectrometry (TGA/MS). It was found that PCC exhibited high thermal stability. The total heat release, peak heat release rate and mean heat release rate of PF containing 4% PCC decreased by 13.55, 33.43 and 13.42%, respectively, in comparison with pristine PF. The enhanced flame-retardant behavior was attributed to the free radicals PO· produced during combustion, which captured free radicals in the gas phase; moreover, the phosphaphenanthrene group may create a char residue barrier against the further combustion of the polymer. Meanwhile, bio-based PFs showed excellent mechanical properties, as the compressive and flexural strength of PF with 4% PCC increased by 79.59 and 20.98%, respectively, in comparison with pristine PF. The pulverization ratio of bio-based PFs was reduced with the increase in PCC content. The findings in this study demonstrate that PCC could be used as a phenol substitute in the synthesis of PFs to overcome their intrinsic brittleness and high flammability.

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References

  1. Hu XM, Wang DM, Cheng WM, Zhou G (2014) Effect of polyethylene glycol on the mechanical property, microstructure, thermal stability, and flame resistance of phenol–urea–formaldehyde foams. J Mater Sci 49:1556–1565. https://doi.org/10.1007/s10853-013-7838-z

    Article  Google Scholar 

  2. Bo C, Wei S, Hu L, Jia P, Liang B, Zhou J, Zhou Y (2016) Synthesis of a cardanol-based phosphorus-containing polyurethane prepolymer and its application in phenolic foams. RSC Adv 6:62999–63005

    Article  Google Scholar 

  3. Shang L, Zhang X, Zhang M, Jin L, Liu L, Xiao L, Li M, Ao Y (2017) A highly active bio-based epoxy resin with multi-functional group: synthesis, characterization, curing and properties. J Mater Sci 53(7):5402–5417. https://doi.org/10.1007/s10853-017-1797-8

    Article  Google Scholar 

  4. Perdriau S, Harder S, Heeres HJ, de Vries JG (2012) Selective conversion of polyenes to monoenes by RuCl(3)-catalyzed transfer hydrogenation: the case of cashew nutshell liquid. Chemsuschem 5:2427–2434

    Article  Google Scholar 

  5. Puchot L, Verge P, Fouquet T, Vancaeyzeele C, Vidal F, Habibi Y (2016) Breaking the symmetry of dibenzoxazines: a paradigm to tailor the design of bio-based thermosets. Green Chem 18:3346–3353

    Article  Google Scholar 

  6. Ma HX, Li JJ, Qiu JJ, Liu Y, Liu CM (2017) Renewable cardanol-based star-shaped prepolymer containing a phosphazene core as a potential biobased green fire-retardant coating. ACS Sustain Chem Eng 5:350–359

    Article  Google Scholar 

  7. Cal E, Maffezzoli A, Mele G, Martina F, Mazzetto SE, Tarzia A, Stifani C (2007) Synthesis of a novel cardanol-based benzoxazine monomer and environmentally sustainable production of polymers and bio-composites. Green Chem 9:754–759

    Article  Google Scholar 

  8. Srivastava R, Srivastava D (2015) Mechanical, chemical, and curing characteristics of cardanol–furfural-based novolac resin for application in green coatings. J Coat Technol Res 12:303–311

    Article  Google Scholar 

  9. Chiverton JP, Ige O, Barnett SJ, Parry T (2017) Multiscale shannon’s entropy modeling of orientation and distance in steel fiber micro-tomography data. IEEE Trans Image Process 26:5284–5297

    Article  Google Scholar 

  10. Liang B, Li X, Hu L, Bo C, Zhou J, Zhou Y (2016) Foaming resol resin modified with polyhydroxylated cardanol and its application to phenolic foams. Ind Crops Prod 80:194–196

    Article  Google Scholar 

  11. Haddadi M, Agoudjil B, Benmansour N, Boudenne A, Garnier B (2017) Experimental and modeling study of effective thermal conductivity of polymer filled with date palm fibers. Polym Compos 38:1712–1719

    Article  Google Scholar 

  12. Wang S, Ma S, Xu C, Liu Y, Dai J, Wang Z, Liu X, Chen J, Shen X, Wei J, Zhu J (2017) Vanillin-derived high-performance flame retardant epoxy resins: facile synthesis and properties. Macromolecules 50:1892–1901

    Article  Google Scholar 

  13. Illy N, Fache M, Ménard R, Negrell C, Caillol S, David G (2015) Phosphorylation of bio-based compounds: the state of the art. Polym. Chem. 6:6257–6291

    Article  Google Scholar 

  14. Xiao F, Wang K, Zhan MS (2012) Atomic oxygen resistant phosphorus-containing polyimides for LEO environment. J Mater Sci 47:4904–4913. https://doi.org/10.1007/s10853-012-6363-9

    Article  Google Scholar 

  15. Choi SW, Sholl DS, Nair S, Moore JS, Liu YJ, Dixit RS, Pendergast JG (2017) Modeling and process simulation of hollow fiber membrane reactor systems for propane dehydrogenation. AIChE J 63:4519–4531

    Article  Google Scholar 

  16. de Sousa Rios MA, Mazzetto SE (2012) Effect of organophosphate antioxidant on the thermo-oxidative degradation of a mineral oil. J Therm Anal Calorim 111:553–559

    Article  Google Scholar 

  17. de Sousa Rios MA, Nascimento TL, Santiago SN, Mazzetto SE (2009) Cashew nut shell liquid: a versatile raw material utilized for syntheses of phosphorus compounds. Energy Fuels 23:5432–5437

    Article  Google Scholar 

  18. Wang X, Zhou S, Guo W, Wang P, Xing W, Song L, Hu Y (2017) Renewable cardanol-based phosphate as a flame retardant toughening agent for epoxy resins. ACS Sustain Chem Eng 5:3409–3416

    Article  Google Scholar 

  19. Bo C, Hu L, Jia P, Liang B, Zhou J, Zhou Y (2015) Structure and thermal properties of phosphorus-containing polyol synthesized from cardanol. RSC Adv 5:106651–106660

    Article  Google Scholar 

  20. Liu Z, Chen J, Knothe G, Nie X, Jiang J (2016) Synthesis of epoxidized cardanol and its antioxidative properties for vegetable oils and biodiesel. ACS Sustain Chem Eng 4:901–906

    Article  Google Scholar 

  21. Zhang M, Luo Z, Zhang J, Chen S, Zhou Y (2015) Effects of a novel phosphorus–nitrogen flame retardant on rosin-based rigid polyurethane foams. Polym Degrad Stab 120:427–434

    Article  Google Scholar 

  22. Riosfacanha M, Mazzetto S, Beserracarioca J, Debarros G (2007) Evaluation of antioxidant properties of a phosphorated cardanol compound on mineral oils (NH10 and NH20). Fuel 86:2416–2421

    Article  Google Scholar 

  23. Wang X, Hu Y, Song L, Xing W, Lu H (2011) Thermal degradation mechanism of flame retarded epoxy resins with a DOPO-substitued organophosphorus oligomer by TG-FTIR and DP-MS. J Anal Appl Pyrol 92:164–170

    Article  Google Scholar 

  24. Jia P, Zhang M, Hu L, Bo C, Zhou Y (2015) Thermal degradation and flame retardant mechanism of poly(vinyl chloride) plasticized with a novel chlorinated phosphate based on soybean oil. Thermochim Acta 613:113–120

    Article  Google Scholar 

  25. Liu Z, Huo J, Yu Y (2017) Water absorption behavior and thermal-mechanical properties of epoxy resins cured with cardanol-based novolac resins and their esterified ramifications. Mater Today Commun 10:80–94

    Article  Google Scholar 

  26. Yen WP, Chen KL, Yeh MY, Uramaru N, Lin HY, Wong FF (2016) Investigation of soluble PEG-imidazoles as the thermal latency catalysts for epoxy-phenolic resins. J Taiwan Inst Chem Eng 59:98–105

    Article  Google Scholar 

  27. Wang F, Huang Z, Liu Y, Li Y (2016) Novel cardanol-containing boron-modified phenolic resin composites. High Perform Polym 29:279–288

    Article  Google Scholar 

  28. van Rijn SP, Srivastava S, Wessels MA, van Soolingen D, Alffenaar JWC, Gumbo T (2017) Sterilizing effect of ertapenem-clavulanate in a hollow-fiber model of tuberculosis and implications on clinical dosing. Antimicrob Agents Chemother 61:e2039–e2116

    Google Scholar 

  29. Gong R, Xu Q, Chu Y, Gu X, Ma J, Li R (2015) A simple preparation method and characterization of epoxy reinforced microporous phenolic open-cell sound absorbent foam. RSC Adv 5:68003–68013

    Article  Google Scholar 

  30. Song SA, Chung YS, Kim SS (2014) The mechanical and thermal characteristics of phenolic foams reinforced with carbon nanoparticles. Composites Sci Technol 103:85–93

    Article  Google Scholar 

  31. Zhou J, Yao Z, Chen Y, Wei D, Xu T (2014) Fabrication and mechanical properties of phenolic foam reinforced with graphene oxide. Polym Compos 35:581–586

    Article  Google Scholar 

  32. Lacoste C, Basso MC, Pizzi A, Laborie MP, Celzard A, Fierro V (2013) Pine tannin-based rigid foams: mechanical and thermal properties. Ind Crops Prod 43:245–250

    Article  Google Scholar 

  33. Jia DW, Shi HJ, Cheng L (2017) Multiscale thermomechanical modeling of short fiber-reinforced composites. Sci Eng Composite Mater 24:765–772

    Google Scholar 

  34. Li Q, Chen L, Li X, Zhang J, Zhang X, Zheng K, Fang F, Zhou H, Tian X (2016) Effect of multi-walled carbon nanotubes on mechanical, thermal and electrical properties of phenolic foam via in situ polymerization. Compos A Appl Sci Manuf 82:214–225

    Article  Google Scholar 

  35. Liu Y, Zhao X, Ye L (2016) A novel elastic urea–melamine–formaldehyde foam: structure and properties. Ind Eng Chem Res 55:8743–8750

    Article  Google Scholar 

  36. Paimushin VN, Firsov VA, Shishkin VM (2017) Modeling the dynamic response of a carbon-fiber-reinforced plate at resonant vibrations considering the internal friction in the material and the external aerodynamic damping. Mech Compos Mater 53:425–440

    Article  Google Scholar 

  37. Fu YG, Li JB (2017) Exact stationary-wave solutions in the standard model of the kerr-nonlinear optical fiber with the bragg grating. J Appl Anal Comput 7:1177–1184

    Google Scholar 

  38. Schartel B, Hull TR (2007) Development of fire-retarded materials—Interpretation of cone calorimeter data. Fire Mater 31:327–354

    Article  Google Scholar 

  39. Xing W, Yang W, Yang W, Hu Q, Si J, Lu H, Yang B, Song L, Hu Y, Yuen RK (2016) Functionalized carbon nanotubes with phosphorus- and nitrogen-containing agents: effective reinforcer for thermal, mechanical, and flame-retardant properties of polystyrene nanocomposites. ACS Appl Mater Interfaces 8:26266–26274

    Article  Google Scholar 

  40. Savas LA, Deniz TK, Tayfun U, Dogan M (2017) Effect of microcapsulated red phosphorus on flame retardant, thermal and mechanical properties of thermoplastic polyurethane composites filled with huntite&hydromagnesite mineral. Polym Degrad Stab 135:121–129

    Article  Google Scholar 

  41. Long L, Chang Q, He W, Xiang Y, Qin S, Yin J, Yu J (2017) Effects of bridged DOPO derivatives on the thermal stability and flame retardant properties of poly(lactic acid). Polym Degrad Stab 139:55–66

    Article  Google Scholar 

  42. Wang X, Hu Y, Song L, Xing W, Lu H, Lv P, Jie G (2010) Flame retardancy and thermal degradation mechanism of epoxy resin composites based on a DOPO substituted organophosphorus oligomer. Polymer 51:2435–2445

    Article  Google Scholar 

  43. Cao Y, Wang XL, Zhang WQ, Yin XW, Shi YQ, Wang YZ (2017) Bi-DOPO structure flame retardants with or without reactive group: their effects on thermal stability and flammability of unsaturated polyester. Ind Eng Chem Res 56:5913–5924

    Article  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the financial support by supported by the Fundamental Research Funds for the Central Non-profit Research Institution of CAF (No. CAFYBB2018MA001) and National Natural Science Foundation of China (Nos. 31470613, 31670577, 31670578).

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Authors and Affiliations

  1. Institute of Chemical Industry of Forest Products, CAF, Nanjing, 210042, Jiangsu Province, China

    Caiying Bo, Xiaohui Yang, Meng Zhang & Yonghong Zhou

  2. National Engineering Laboratory for Biomass Chemical Utilization, Nanjing, 210042, Jiangsu Province, China

    Caiying Bo, Xiaohui Yang, Meng Zhang & Yonghong Zhou

  3. Key and Open Laboratory on Forest Chemical Engineering, SFA, Nanjing, 210042, Jiangsu Province, China

    Caiying Bo, Xiaohui Yang, Meng Zhang & Yonghong Zhou

  4. Key Laboratory Biomass Energy and Material, Nanjing, 210042, Jiangsu Province, China

    Caiying Bo, Xiaohui Yang, Meng Zhang & Yonghong Zhou

  5. Institute of New Technology of Forestry, CAF, Beijing, 100091, China

    Lihong Hu

  6. State Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, China

    Yong Chen

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  1. Caiying Bo
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Correspondence to Meng Zhang or Yonghong Zhou.

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Bo, C., Hu, L., Chen, Y. et al. Synthesis of a novel cardanol-based compound and environmentally sustainable production of phenolic foam. J Mater Sci 53, 10784–10797 (2018). https://doi.org/10.1007/s10853-018-2362-9

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  • DOI: https://doi.org/10.1007/s10853-018-2362-9

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