Synthesis and characterization of a novel epoxy resin based on cyclotriphosphazene and its thermal degradation and flammability performance

Polymer Degradation and Stability

Volumn 109, Issue , 2014, Pages 240-248

  Xu, Guang Rui ^a   Xu, Miao Jun ^a   Li, Bin ^a  

^a NORTHEAST FORESTRY UNIVERSITY   (China)

Author keywords

Cyclotriphosphazene; Epoxy resin; Flame retardancy; Synthesis; Thermal degradation

Indexed keywords

COMBUSTION; ENTHALPY; EPOXY RESINS; FLAME RETARDANTS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; METHANE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYROLYSIS; SCANNING ELECTRON MICROSCOPY; SYNTHESIS (CHEMICAL); THERMOANALYSIS; THERMOSETS;

CYCLOTRIPHOSPHAZENES; DIGLYCIDYL ETHER OF BISPHENOL-A; DYNAMIC MECHANICAL THERMAL ANALYSIS; FLAME RETARDANCY; FLAME RETARDANT PROPERTIES; FLAME-RETARDANT MECHANISMS; HEXACHLOROCYCLOTRIPHOSPHAZENE; SYNTHESIS AND CHARACTERIZATIONS;

CURING; EPOXY RESINS;

EID: 84907318167     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2014.07.020     Document Type: Article

References (43)

1. X. Wang, Y. Hu, L. Song, W. Xing, and H. Lu 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 1 2011 164 170
2. J. Wan, C. Li, Z.Y. Bu, C.J. Xu, B.G. Li, and H. Fan A comparative study of epoxy resin cured with a linear diamine and a branched polyamine Chem Eng J 188 2012 160 172
3. Y. Nakamura, M. Yamaguchi, M. Okubo, and T. Matsumoto Effects of particle size on mechanical and impact properties of epoxy resin filled with spherical silica J App Polym Sci 45 7 1992 1281 1289 (Pubitemid 23621145)
4. B.K. Kandola, B. Biswas, D. Price, and A.R. Horrocks Studies on the effect of different levels of toughener and flame retardants on thermal stability of epoxy resin Polym Degrad Stab 95 2 2010 144 152
5. T.S. Leu Structure and characterization for conterminously linked polymer of short-chain epoxy resin with triallyl isocyanurate and bismaleimide J App Polym Sci 102 3 2006 2470 2480
6. M.P. Luda, A.I. Balabanovich, and M. Zanetti Pyrolysis of fire retardant anhydride-cured epoxy resins J Anal Appl Pyrol 88 1 2010 39 52
7. M.A. Uddin, T. Bhaskar, T. Kusaba, K. Hamano, A. Muto, and Y. Sakata Debromination of flame retardant high impact polystyrene (HIPS-Br) by hydrothermal treatment and recovery of bromine free plastics Green Chem 5 2 2003 260 263 (Pubitemid 37487490)
8. S.Y. Lu, and I. Hamerton Recent developments in the chemistry of halogen-free flame retardant polymers Prog Polym Sci 27 8 2002 1661 1712 (Pubitemid 34811634)
9. X. Wang, L. Song, W. Xing, H. Lu, and Y. Hu A effective flame retardant for epoxy resins based on poly(DOPO substituted dihydroxyl phenyl pentaerythritol diphosphonate) Mater Chem Phys 125 3 2011 536 541
10. S. Sun, Y. He, X. Wang, and D. Wu Flammability characteristics and performance of halogen-free flame-retarded polyoxymethylene based on phosphorus-nitrogen synergistic effects J App Polym Sci 118 1 2010 611 622
11. F. Gao, L. Tong, and Z. Fang Effect of a novel phosphorous-nitrogen containing intumescent flame retardant on the fire retardancy and the thermal behaviour of poly(butylene terephthalate) Polym Degrad Stab 91 6 2006 1295 1299 (Pubitemid 43673817)
12. M. Gao, and S. Yang A novel intumescent flame-retardant epoxy resins system J App Polym Sci 115 4 2010 2346 2351
13. S.V. Levchik, and E.D. Weil Thermal decomposition, combustion and flame-retardancy of epoxy resins-a review of the recent literature Polym Int 53 12 2004 1901 1929 (Pubitemid 39605503)
14. K. Wu, L. Song, Y. Hu, H. Lu, B.K. Kandola, and E. Kandare Synthesis and characterization of a functional polyhedral oligomeric silsesquioxane and its flame retardancy in epoxy resin Prog Org Coat 65 4 2009 490 497
15. Y.L. Liu, G.H. Hsiue, R.H. Lee, and Y.S. Chiu Phosphorus-containing epoxy for flame retardant. III: using phosphorylated diamines as curing agents J App Polym Sci 63 7 1997 895 901
16. L.P. Gao, D.Y. Wang, Y.Z. Wang, J.S. Wang, and B. Yang A flame-retardant epoxy resin based on a reactive phosphorus-containing monomer of DODPP and its thermal and flame-retardant properties Polym Degrad Stab 93 7 2008 1308 1315
17. H. Ren, J. Sun, B. Wu, and Q. Zhou Synthesis and properties of a phosphorus-containing flame retardant epoxy resin based on bis-phenoxy (3-hydroxy) phenyl phosphine oxide Polym Degrad Stab 92 6 2007 956 961 (Pubitemid 46734336)
18. A. Toldy, P. Anna, I. Csontos, A. Szabó, and G.y. Marosi Intrinsically flame retardant epoxy resin-Fire performance and background-Part I Polym Degrad Stab 92 12 2007 2223 2230 (Pubitemid 350180046)
19. A. Toldy, B. Szolnoki, I. Csontos, and G. Marosi Green chemistry approach for synthesizing phosphorus flame retardant crosslinking agents for epoxy resins J App Polym Sci 131 2014 40105
20. C.S. Wang, and J.Y. Shieh Synthesis and properties of epoxy resins containing bis(3-hydroxyphenyl) phenyl phosphate Eur Polym J 36 3 2000 443 452
21. H. Liu, K. Xu, H. Ai, L. Zhang, and M. Chen Preparation and characterization of phosphorus-containing Mannich-type bases as curing agents for epoxy resin Polym Advan Technol 20 9 2009 753 758
22. U. Diefenbach, and H.R. Allcock Synthesis of cyclo- and polyphosphazenes with pyridine side groups Inorg Chem 33 20 1994 4562 4565
23. L. Zhu, Y. Zhu, Y. Pan, Y. Huang, X. Huang, and X. Tang Fully crosslinked poly[cyclotriphosphazene-co-(4, 4′-sulfonyldiphenol)] microspheres via precipitation polymerization and their superior thermal properties Macromol React Eng 1 1 2007 45 52
24. R. Liu, and X. Wang Synthesis, characterization, thermal properties and flame retardancy of a novel nonflammable phosphazene-based epoxy resin Polym Degrad Stab 94 4 2009 617 624
25. Y.W. Chen-Yang, C.Y. Yuan, C.H. Li, and H.C. Yang Preparation and characterization of novel flame retardant (aliphatic phosphate) cyclotriphosphazene-containing polyurethanes J App Polym Sci 90 5 2003 1357 1364 (Pubitemid 37157874)
26. H.R. Allcock, and P.E. Austin Schiff base coupling of cyclic and high-polymeric phosphazenes to aldehydes and amines: chemotherapeutic models Macromolecules 14 6 1981 1616 1622
27. M. El Gouri, A. El Bachiri, S.E. Hegazi, M. Rafik, and A. El Harfi Thermal degradation of a reactive flame retardant based on cyclotriphosphazene and its blend with DGEBA epoxy resin Polym Degrad Stab 94 11 2009 2101 2106
28. M. El Gouri, A. El Bachiri, S.E. Hegazi, M. Rafik, and A. El Harfi A phosphazene compound multipurpose application-Composite material precursor and reactive flame retardant for epoxy resin materials J Mater Environ Sci 2 4 2011 319 334
29. Y. Bai, X.D. Wang, and D. Wu Novel cyclolinear cyclotriphosphazene-linked epoxy resin for halogen-free fire resistance: synthesis, characterization, and flammability characteristics Ind Eng Chem Res 51 46 2012 15064 15074
30. G.Y. You, Z. Cai, H. Peng, X.S. Tan, and H.W. He A well-defined cyclotriphosphazene-based epoxy monomer and its application as a novel epoxy resin: synthesis, curing behaviors, and flame retardancy Phosphorus Sulfur Silicon Relat Elem 189 4 2014 541 550
31. You GY, He HW, Huang Y, Cai Z. Phosphonitrilic chloride trimer epoxy compound with flame-retardant property and preparation and application thereof. CN 102503982A; 2012-6-20.
32. J. Ding, and W. Shi Thermal degradation and flame retardancy of hexaacrylated/hexaethoxyl cyclophosphazene and their blends with epoxy acrylate Polym Degrad Stab 84 1 2004 159 165
33. D. Kumar, G.M. Fohlen, and J.A. Parker Fire-and heat-resistant laminating resins based on maleimido-substituted aromatic cyclotriphosphazenes Macromolecules 16 8 1983 1250 1257
34. C.J. Orme, J.R. Klaehn, M.K. Harrup, R.P. Lash, and F.F. Stewart Characterization of 2-(2-methoxyethoxy) ethanol-substituted phosphazene polymers using pervaporation, solubility parameters, and sorption studies J App Polym Sci 97 3 2005 939 945 (Pubitemid 41162191)
35. D. Kumar, M. Khullar, and A.D. Gupta Synthesis and characterization of novel cyclotriphosphazene-containing poly (etherimide)s Polymer 34 14 1993 3025 3029
36. B.C. Bing, and B. Li Synthesis, thermal property and hydrolytic degradation of star-shaped hexa[p-(carbonyl glycino methyl ester) phenoxy] cyclotriphosphazene Sci China Ser B 52 12 2009 2186 2194
37. W.Z. Yuan, X.Z. Tang, X.B. Huang, and S.X. Zheng Synthesis, characterization and thermal properties of hexaarmed star-shaped poly(ε-caprolactone)-b-poly(D,L-lactide-co-glycolide) initiated with hydroxyl-terminated cyclotriphosphazene Polymer 46 5 2005 1701 1707
38. C.W. Allen Regio- and stereochemical control in substitution reactions of cyclophosphazenes Chem Rev 91 2 1991 119 135
39. J.Y. Chang, S.B. Rhee, S. Cheong, and M. Yoon Synthesis and thermal reaction of acetylenic group substituted poly (organophosphazenes) and cyclotriphosphazene Macromolecules 25 10 1992 2666 2670
40. S. Chen, Q. Zheng, G. Ye, and G. Zheng Fire-retardant properties of the viscose rayon containing alkoxycyclotriphosphazene J App Polym Sci 102 1 2006 698 702 (Pubitemid 44518473)
41. C.Y. Yuan, S.Y. Chen, C.H. Tsai, Y.S. Chiu, and Y.W. Chen-Yang Thermally stable and flame-retardant aromatic phosphate and cyclotriphosphazene-containing polyurethanes: synthesis and properties Polym Advan Technol 16 5 2005 393 399 (Pubitemid 40707109)
42. L.J. Qian, L. Ye, Y. Qiu, and S. Qu Thermal degradation behavior of the compound containing phosphaphenanthrene and phosphazene groups and its flame retardant mechanism on epoxy resin Polymer 52 24 2011 5486 5493
43. D.A. Conner, D.T. Welna, Y. Chang, and H.R. Allcock Influence of terminal phenyl groups on the side chains of phosphazene polymers: structure-property relationships and polymer electrolyte behavior Macromolecules 40 2 2007 322 328