Developing high performance cyanate ester resin with significantly reduced postcuring temperature while improved toughness, rigidity, thermal and dielectric properties based on manganese-Schiff base hybridized graphene oxide

Chemical Engineering Journal

Volumn 298, Issue , 2016, Pages 214-224

  Gu, Xing ^a   Zhang, Zhijuan ^a   Yuan, Li ^a   Liang, Guozheng ^a   Gu, Aijuan ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

Catalyst; Crosslinking; Graphene oxide; Hybrid; Resin; Toughening

Indexed keywords

CATALYSTS; CROSSLINKING; CURING; CUTTING; DIELECTRIC LOSSES; DIELECTRIC PROPERTIES; ENERGY CONSERVATION; ESTERS; GLASS TRANSITION; GRAPHENE; MANGANESE; MANGANESE OXIDE; RIGIDITY; THERMOSETS; TOUGHENING;

COMPREHENSIVE PERFORMANCE; CROSS-LINKED NETWORKS; CROSSLINKED STRUCTURES; CYANATE ESTER RESINS; GRAPHENE OXIDES; HYBRID; THERMAL AND DIELECTRIC PROPERTIES; THERMAL DEGRADATION TEMPERATURES;

RESINS;

EID: 84964335847     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2016.04.031     Document Type: Article

References (66)

1. Wan J.T., Gan B., Li C., Molina-Aldareguia J., Kalali E.N., Wang X., Wang D.Y. A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: synthesis, curing kinetics and structure-property relationship. Chem. Eng. J. 2016, 284:1080-1093.
2. Jiao Y.C., Yuan L., Liang G.Z., Gu A.J. Dispersing carbon nanotubes in the unfavorable phase of an immiscible reverse-phase blend with Haake instrument to fabricate high-k nanocomposites with extremely low dielectric loss and percolation threshold. Chem. Eng. J. 2016, 285:650-659.
3. Wang X., Xing W.Y., Feng X.M., Yu B., Lu H.D., Song L., Hu Y. The effect of metal oxide decorated graphene hybrids on the improved thermal stability and the reduced smoke toxicity in epoxy resins. Chem. Eng. J. 2014, 250:214-221.
4. Wang B.H., Liu L.M., Huang L.Z., Chi L.F., Liang G.Z., Yuan L., Gu A.J. Fabrication and origin of high-k carbon nanotube/epoxy composites with low dielectric loss through layer-by-layer casting technique. Carbon 2015, 85:28-37.
5. Wu H.C., Kessler M.R. Multifunctional cyanate ester nanocomposites reinforced by hexagonal boron nitride after noncovalent biomimetic functionalization. ACS Appl. Mater. Interfaces 2015, 7:5915-5926.
6. Wang Y.Q., Kou K.C., Wu G.L., Zhuo L.H., Li J.L., Zhang Y. The curing reaction of benzoxazine with bismaleimide/cyanate ester resin and the properties of the terpolymer. Polymer 2015, 77:354-360.
7. Zhang X.H., Liang G.Z., Chang J.F., Gu A.J., Yuan L., Zhang W. The origin of the electric and dielectric behavior of expanded graphite-carbon nanotube/cyanate ester composites with very high dielectric constant and low dielectric loss. Carbon 2012, 50:4995-5007.
8. Li X.D., Gu Y. The co-curing process of a benzoxazine-cyanate system and the thermal properties of the copolymers. Polym. Chem. 2011, 2:2778-2781.
9. Chen X.X., Liang G.Z., Gu A.J., Yuan L. Flame retarding cyanate ester resin with low curing temperature, high thermal resistance, outstanding dielectric property, and low water absorption for high frequency and high speed printed circuit broads. Ind. Eng. Chem. Res. 2015, 54:1806-1815.
10. Zhang M.M., Yan H.X., Yang X.W., Liu C. Effect of functionalized graphene oxide with a hyperbranched cyclotriphosphazene polymer on mechanical and thermal properties of cyanate ester composites. RSC Adv. 2014, 4:45930-45938.
11. De B., Voit B., Karak N. Transparent luminescent hyperbranched epoxy/carbon oxide dot nanocomposites with outstanding toughness and ductility. ACS Appl. Mater. Interfaces 2013, 5:10027-10034.
12. Zhang Z.Y., Yuan L., Liang G.Z., Gu A.J., Qiang Z.X., Yang C.W., Chen X.X. Unique hybridized carbon nanotubes and their high performance flame retarding composites with high smoke suppression, good toughness and low curing temperature. J. Mater. Chem. A 2014, 2:4975-4988.
13. Wang M.W., Jeng R.J., Lin C.H. Origin of the rapid trimerization of cyanate ester in a benzoxazine/cyanate ester blend. Macromolecules 2015, 48:2417-2421.
14. Ma J.X., Lei X.F., Tian D., Yuan L.J., Liao C.S. Curing behavior and network formation of cyanate ester resin/polyethylene glycol. J. Appl. Polym. Sci. 2015, 132:41841.
15. Lin C., Yuan L., Gu A.J., Chen F., Liang G.Z. High performance cyanate ester resins/reactive porous polymeric microsphere systems with low-temperature processability. Compos. Sci. Technol. 2013, 85:148-155.
16. Dai S.K., Zhuo D.X., Gu A.J., Liang G.Z., Yuan L. A novel hybrid catalyst system and its effects on the curing, thermal, and dielectric properties of cyanate ester. Polym. Eng. Sci. 2011, 51:2236-2244.
17. Gómez C.M., Recalde I.B., Mondragon I. Kinetic parameters of a cyanate ester resin catalyzed with different proportions of nonylphenol and cobalt acetylacetonate catalyst. Eur. Polymer J. 2005, 41:2734-2741.
18. Li Q.F., Lu K., Yang Q.Q., Jin R.G. The effect of different metallic catalysts on the coreaction of cyanate/epoxy. J. Appl. Polym. Sci. 2006, 100:2293-2302.
19. Mathew D., Nair C.P.R., Krishnan K., Ninan K.N. Catalysis of the cure reaction of bisphenol a dicyanate. A DSC study. J. Polym. Sci. Part A: Polym. Chem. 1999, 37:1103-1114.
20. Fang T., Shimp D.A. Polycyanate esters: science and applications. Prog. Polym. Sci. 1995, 20:61-118.
21. Chen Y.J., Yang C.Z., Guo Z.H., Zhang Y., Cheng J., Fang Z.P. Irradiation treatment of multiwalled carbon nanotubes and its effect on the thermal properties of their composites with epoxy resin. Carbon 2012, 50:3119.
22. Li J.W., Wu Z.X., Huang C.J., Liu H.M., Huang R.J., Li L.F. Mechanical properties of cyanate ester/epoxy nanocomposites modified with plasma functionalized MWCNTs. Compos. Sci. Technol. 2014, 90:166-173.
23. 2 electrospun fibres with controllable structure and their novel high-performance composites with outstanding thermal, mechanical and dielectric properties. J. Compos. Mater. 2014, 48:3201-3214.
24. 2) nanomaterials for low k dielectric applications. RSC Adv. 2013, 3:12915-12921.
25. Noparvar-Qarebagh A., Roghani-Mamaqani H., Salami-Kalajahi M. Novolac phenolic resin and graphene aerogel organic-inorganic nanohybrids: high carbon yields by resin modification and its incorporation into aerogel network. Polym. Degrad. Stab. 2016, 124:1-14.
26. Noparvar-Qarebagh A., Roghani-Mamaqani H., Salami-Kalajahi M. Organic-inorganic nanohybrids of novolac phenolic resin and carbon nanotube: high carbon yields by using carbon nanotube aerogel and resin incorporation into aerogel network. Microporous Mesoporous Mater. 2016, 224:58-67.
27. Saeb M.R., Najafi F., Bakhshandeh E., Khonakdar H.A., Mostafaiyan M., Simon F., Scheffler C., M'der E. Highly curable epoxy/MWCNTs nanocomposites: an effective approach to functionalization of carbon nanotubes. Chem. Eng. J. 2015, 259:117-125.
28. Trakakis G., Anagnostopoulos G., Sygellou L., Bakolas A., Parthenios J., Tasis D., Galiotis C., Papagelis K. Epoxidized multi-walled carbon nanotube buckypapers: a scaffold for polymer nanocomposites with enhanced mechanical properties. Chem. Eng. J. 2015, 281:793-803.
29. Sheng X., Akinc M., Kessler M.R. Rheology and dynamic mechanical analysis of bisphenol E cyanate ester/alumina nanocomposites. Polym. Eng. Sci. 2010, 50:302-311.
30. Chandrasekaran S., Stao N., Tölle F., Mulhaupt R., Fiedler B., Schulte K. Fracture toughness and failure mechanism of graphene based epoxy composites. Compos. Sci. Technol. 2014, 97:90-99.
31. Wooster T.J., Abrol S., MacFarlane D.R. Cyanate ester polymerization catalysis by layered-silicates. Polymer 2004, 45:7845-7852.
32. Nair C.P.R., Mathew D., Ninan K.N. New polymerization techniques and synthetic methodologies. Adv. Polym. Sci. 2001, 155:1-99.
33. Wang X., Jin J., Song M. Cyanate ester resin/graphene nanocomposite: curing dynamics and network formation. Eur. Polymer J. 2012, 48:1034-1041.
34. Lin Q.L., Qu L.J., Lü Q.F., Fang C.Q. Preparation and properties of graphene oxide nanosheets/cyanate ester resin composites. Polym. Testing 2013, 32:330-337.
35. Hummers W.S., Offeman R.E. Preparation of graphitic oxide. J. Am. Chem. Soc. 1958, 80:1339.
36. Baskaran D., Mays J.W., Bratcher M.S. Noncovalent and nonspecific molecular interactions of polymers with multiwalled carbon nanotubes. Chem. Mater. 2005, 13:3389-3397.
37. Yan J.L., Chen G.J., Cao J., Yang W., Xie B.H., Yang M.B. Functionalized graphene oxide with ethylenediamine and 1,6-hexanediamine. New Carbon Mater. 2012, 27:370-376.
38. Zhang Y., Zhang S., Chung T.S. Nanometric graphene oxide framework membranes with enhanced heavy metal removal via nanofiltration. Environ. Sci. Technol. 2015, 49:10235-10242.
39. Sun J., Zhang J., Wang L., Zhu L.F., Meng X.J., Xiao F.S. Co-salen functionalized on graphene as an efficient heterogeneous catalyst for cyclohexene oxidation. J. Energy Chem. 2013, 22:48-51.
40. Li Z.F., Wu S.J., Ding H., Zheng D.F., Hu J., Wang X., Huo Q.S., Guan J.Q., Kan Q.B. Immobilized Cu(II) and Co(II) salen complexes on graphene oxide and their catalytic activity for aerobic epoxidation of styrene. New J. Chem. 2013, 37:1561-1568.
41. Zhao Q.S., Bai C., Zhang W.F., Li Y., Zhang G.L., Zhang F.B., Fan X.B. Catalytic epoxidation of olefins with graphene oxide supported copper (salen) complex. Ind. Eng. Chem. Res. 2014, 53:4232-4238.
42. Zou X.C., Shi K.Y., Wang C. Chiral MnIII (salen) supported on tunable phenoxyl group modified zirconium poly (styrene-phenylvinylphosphonate)-phosphate as an efficient catalyst for epoxidation of unfunctionalized olefins. Chin. J. Catal. 2014, 35:1446-1455.
43. Lerf A., Buchsteiner A., Pieper J., Schöttl S., Dekany I., Szabo T., Boehm H.P. Hydration behavior and dynamics of water molecules in graphite oxide. J. Phys. Chem. Solids 2006, 67:1106-1110.
44. Hong S.G., Yeh C.S. Catalytic effects of copper oxides on the curing and degradation reactions of cyanate ester resin. J. Appl. Polym. Sci. 2007, 104:442-448.
45. Lin Y., Stone C.A., Shaw S.J., Song M. Effect of carbon nanotubes on the curing dynamics and network formation of cyanate ester resin. J. Polym. Res. 2013, 20:1-12.
46. Li W.F., Liang G.Z., Xin W.L. Triazine reaction of cyanate ester resin systems catalyzed by organic tin compound: kinetics and mechanism. Polym. Int. 2004, 53:869-876.
47. Fry C.G., Lind A.C. Determination of crosslink density in thermoset polymers by use of solid-state proton NMR techniques. Macromolecules 1988, 5:1292-1297.
48. Yoonessi M., Lebrón-Colón M., Scheiman D., Meador M.A. Carbon nanotube epoxy nanocomposites: the effects of interfacial modifications on the dynamic mechanical properties of the nanocomposites. ACS Appl. Mater. Interfaces 2014, 6:16621-16630.
49. Jiang F., Zhang Y.Q., Wang Z.K., Wang W.T., Xu Z.H., Wang Z.G. Combination of magnetic and enhanced mechanical properties for copolymer-grafted magnetite composite thermoplastic elastomers. ACS Appl. Mater. Interfaces 2015, 7:10563-10575.
50. Zhao L., Yuan L., Liang G.Z., Gu A.J. Novel tough and thermally stable cyanate ester resins with high flame retardancy, low dielectric loss and constant based on a phenolphthalein type polyarylether sulfone. RSC Adv. 2015, 5:58989-59002.
51. Ling W., Gu A.J., Liang G.Z., Yuan L., Liu J. Dynamic mechanical properties of aluminum nitride/cyanate ester composites for high performance electronic packaging. Polym. Adv. Technol. 2010, 21:365-370.
52. Huang P.Z., Gu A.J., Liang G.Z., Yuan L. Curing behavior and dielectric properties of hyperbranched poly(phenylene oxide)/cyanate ester resins. J. Appl. Polym. Sci. 2011, 121:2113-2122.
53. Zhao L., Liu P., Liang G.Z., Gu A.J., Yuan L., Guan Q.B. The origin of the curing behavior, mechanical and thermal properties of surface functionalized attapulgite/bismaleimide/diallylbisphenol composites. Appl. Surf. Sci. 2014, 288:435-443.
54. Yang H.F., Li F.H., Shan C.S., Han D.X., Zhang Q.X., Niu L., Ivaska A. Covalent functionalization of chemically converted graphene sheets via silane and its reinforcement. J. Mater. Chem. 2009, 19:4632-4638.
55. Ren F., Zhu G.M., Ren P.G., Wang Y.K., Cui X.P. In situ polymerization of graphene oxide and cyanate ester-epoxy with enhanced mechanical and thermal properties. Appl. Surf. Sci. 2014, 316:549-557.
56. Hong N.N., Nie S.B., Song L., Tai Q.L., Zhang P., Wang B.B., Qian X.D., Hu Y. Controllable synthesis of multi-layer graphene flakes and multi-wall carbon nanotubes from pyrolyzing biodegradable poly (butylene succinate) composites. Mater. Lett. 2011, 65:2707-2710.
57. Chaudhary S., Surekha P., Kumar D., Rajagopal C., Roy P.K. Amine-functionalized poly (styrene) microspheres as thermoplastic toughener for epoxy resin. Polym. Compos. 2015, 36:174-183.
58. Liang Y.L., Pearson R.A. Toughening mechanisms in epoxy-silica nanocomposites (ESNs). Polymer 2009, 50:4895-4905.
59. Kitey R., Tippur H.V. Role of particle size and filler-matrix adhesion on dynamic fracture of glass-filled epoxy. II. Linkage between macro-and micro-measurements. Acta Mater. 2005, 53:1167-1178.
60. Lange F.F. The interaction of a crack front with a second-phase dispersion. Phil. Mag. 1970, 22:983-992.
61. Wu S.Y., Ladani R.B., Zhang J., Bafekrpour E., Ghorbani K., Mouritz A.P., Kinloch A.J., Wang C.H. Aligning multilayer graphene flakes with an external electric field to improve multifunctional properties of epoxy nanocomposites. Carbon 2015, 94:607-618.
62. Marieta C., Schulz E., Irusta L., Gabilondo N., Tercjak A., Mondragon I. Evaluation of fiber surface treatment and toughening of thermoset matrix on the interfacial behaviour of carbon fiber-reinforced cyanate matrix composites. Compos. Sci. Technol. 2005, 65:2189-2197.
63. Zhuo D.X., Gu A.J., Liang G.Z., Hu J.T., Yuan L., Ji L.F. Novel hyperbranched polyphenylsilsesquioxane-modified cyanate ester resins with improved toughness and stiffness. Polym. Int. 2011, 60:1277-1286.
64. Wang J.H., Liang G.Z., He S.B., Yang L.L. Curing behavior and mechanical properties of hollow glass microsphere/bisphenol a dicyanate ester composites. J. Appl. Polym. Sci. 2010, 118:1252-1256.
65. John B., Nair C.P.R., Ninan K.N. Effect of nanoclay on the mechanical, dynamic mechanical and thermal properties of cyanate ester syntactic foams. Mater. Sci. Eng., A 2010, 527:5435-5443.
66. Dong C.S., Davies I.J. Flexural and tensile strengths of unidirectional hybrid epoxy composites reinforced by S-2 glass and T700S carbon fibers. Mater. Des. 2014, 54:955-966.