Citation: Weng Zhi-Huan, Qi Yu, Zong Li-Shuai, Liu Cheng, Wang Jin-Yan, Jian Xi-Gao. Multiple-SO₃H functioned ionic liquid as efficient curing agent for phthalonitrile-terminated poly(phthalazinone ether nitrile)[J]. Chinese Chemical Letters, ;2017, 28(5): 1069-1073. doi: 10.1016/j.cclet.2016.12.019 shu

Multiple-SO₃H functioned ionic liquid as efficient curing agent for phthalonitrile-terminated poly(phthalazinone ether nitrile)

Weng Zhi-Huan ^a,b,c ,
Qi Yu ^b,c ,
Zong Li-Shuai ^b,c ,
Liu Cheng ^a,b,c ,
Wang Jin-Yan ^a,b,c,, ,
Jian Xi-Gao ^a,b,c

a.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
b.
Liaoning High Performance Resin Engineering Research Center, Dalian University of Technology, Dalian 116024, China
c.
Department of Polymer Science & Materials, Dalian University of Technology, Dalian 116024, China

Corresponding author: Wang Jin-Yan, wangjinyan@dlut.edu.cn
Received Date: 10 October 2016
Revised Date: 24 November 2016
Accepted Date: 29 November 2016
Available Online: 16 May 2016

Figures(7)

Combined with the advantages of low melting point, high thermal stability and strong acidity, a multipleSO₃H functioned ionic liquid (MIL) was developed successfully as a curing agent to promote the curing reaction of phthalonitrile-terminated poly(phthalazinone ether nitrile) (PPEN-Ph). The curing kinetics over differential scanning calorimetry (DSC) showed that both the initial curing temperature T_p0' and apparent activation energy Ea' (based on Kissinger equation) were reduced significantly over MIL (207.9℃ and 101.5 kJ/mol) compared to the common curing agent ZnCl₂ (268.5℃ and 201.5 kJ/mol). Moreover, under identical curing conditions, the resulting thermosetting resin over former (T_d5%=526.1℃) showed better thermal stability than that over latter (T_d5%=512.1℃). These results indicated that MIL should be a good candidate as a curing agent for phthalonitrile resins.
- Ionic liquid,
- Phthalonitrile resin,
- Phthalazinone,
- Thermal stability,
- Curing agent
1. [1]
  S.B. Sasri, T.M. Keller. Phthalonitrile cure reaction with aromatic diamines[J]. J. Polym. Sci. A:Polym. Chem., 1998,36:1885-1890. doi: 10.1002/(ISSN)1099-0518
2. [2]
  T.M. Keller, D.D. Dominguez. High temperature resorcinol-based phthalonitrile polymer[J]. Polymer, 2005,46:4614-4618. doi: 10.1016/j.polymer.2005.03.068
3. [3]
  Z.J. Pu, X. Huang, L. Chen. Effect of nitrile-functionalization and thermal cross-linking on the dielectric and mechanical properties of PEN/CNTs-CN composites[J]. J. Mater. Sci. Mater. Electron., 2013,24:2913-2922. doi: 10.1007/s10854-013-1190-6
4. [4]
  W.H. Zhu, G.S. Wu. Molecular design for octupolar nonlinear optical systems:an ab initio study of first hyperpolarizabilities of symmetrically heteroaromatic-substituted triazines[J]. J. Phys. Chem. A, 2001,105:9568-9574. doi: 10.1021/jp0120559
5. [5]
  T.M. Keller. Synthesis and polymerization of multiple aromatic ether phthalonitrile[J]. Chem. Mater., 1994,6:302-305. doi: 10.1021/cm00039a009
6. [6]
  X.Y. Yu, K. Naito, C. Kang. Synthesis and properties of a high-temperature naphthyl-based phthalonitrile polymer[J]. Macromol. Chem. Phys., 2013,214:361-369. doi: 10.1002/macp.201200492
7. [7]
  X. Fu, G.P. Yu, C. Liu. Phthalonitrile-functional multiple arylene ether nitrile-containing phthalazinone moiety:facile synthesis, curing, and properties[J]. High Perform. Polym., 2014,26:540-549. doi: 10.1177/0954008314522822
8. [8]
  W.T. Li, F. Zuo, K. Jia. Study of catalytic effect of ammonium molybdate on the bisphthalonitrile resins curing reaction with aromatic amine[J]. Chin. Chem. Lett., 2009,20:348-351. doi: 10.1016/j.cclet.2008.11.018
9. [9]
  M. Laskoski, A. Neal, T.M. Keller. Improved synthesis of oligomeric phthalonitriles and studies designed for low temperature[J]. J. Polym. Sci. A:Polym. Chem., 2014,52:1662-1668. doi: 10.1002/pola.v52.12
10. [10]
  H.T. Sheng, X.G. Peng, H. Guo. Synthesis of high performance bisphthalonitrile resins cured with self-catalyzed 4-aminophenoxy phthalonitrile[J]. Thermochim. Acta, 2014,577:17-24. doi: 10.1016/j.tca.2013.12.010
11. [11]
  T.M. Robert, D. Augustine, S.M. Chandran. Graphene oxide induced fast curing of amino novolac phthalonitrile[J]. RSC Adv., 2015,5:1198-1204. doi: 10.1039/C4RA08751H
12. [12]
  H. Zhou, A. Badashah, Z. Luo. Preparation and property comparison of ortho meta, and para autocatalytic phthalonitrile compounds with amino group[J]. Polym. Adv. Technol., 2011,22:1459-1465. doi: 10.1002/pat.v22.10
13. [13]
  K. Zeng, H.B. Hong, S.H. Zhou. A new soluble aramide with pendant phthalonitrile units and polymer property enhancement by nitrile cure reactions[J]. Polymer, 2009,50:5002-5006. doi: 10.1016/j.polymer.2009.08.033
14. [14]
  H. Zhang, T. Liu, W. Yan. Synthesis and properties of cross-linkable poly (aryl ether ketone) oligomers terminated with phthalonitrile group[J]. High Perform. Polym., 2014,26:1007-1014. doi: 10.1177/0954008314536594
15. [15]
  M. Vafaeezadeh, H .. Alinezhad, Brønsted acidic ionic liquids:green catalysts for essential organic reactions[J]. J. Mol. Liq., 2016,218:95-105. doi: 10.1016/j.molliq.2016.02.017
16. [16]
  C.M. Wang, L.P. Guo, H.R. Li. Preparation of simple ammonium ionic liquids and their application in the cracking of dialkoxypropanes[J]. Green Chem., 2006,8:603-607. doi: 10.1039/b600041j
17. [17]
  J. Esser, P. Wasserscheid, A. Jess. Deep desulfurization of oil refinery streams by extraction with ionic liquids[J]. Green Chem., 2004,6:316-322. doi: 10.1039/B407028C
18. [18]
  A.J. Carmichael, M.J. Earle, J.D. Holbrey. The Heck reaction in ionic liquids:a multiphasic catalyst system[J]. Org. Lett., 1999,1:997-1000. doi: 10.1021/ol9907771
19. [19]
  R.T. Carlin, J.S. Wilkes. Complexation of Cp₂MCl₂ in a chloroaluminate molten salt:relevance to homogeneous Ziegler-Natta catalysis[J]. J. Mol. Catal., 1990,63:125-129. doi: 10.1016/0304-5102(90)85135-5
20. [20]
  S.H. Bao, N.N. Quan, J. Zhang. Alkylation of p-cresol with tert-butanol catalyzed by novel multiple-SO₃H functioned ionic liquid[J]. Chin. J. Chem. Eng., 2011,19:64-69. doi: 10.1016/S1004-9541(09)60178-6
21. [21]
  G.P. Yu, C. Liu, J.Y. Wang. Synthesis, characterization, and crosslinking of soluble cyano-containing poly(arylene ether)s bearing phthalazinone moiety[J]. Polymer, 2010,51:100-109. doi: 10.1016/j.polymer.2009.11.017
22. [22]
  C. Liu, J.Y. Wang, E.C. Lin. Synthesis and properties of phthalonitrileterminated oligomeric poly(ether imide)s containing phthalazinone moiety[J]. Polym. Degrad. Stab., 2012,97:460-468. doi: 10.1016/j.polymdegradstab.2011.11.001
23. [23]
  G.P. Yu, C. Liu, X.P. Li. Highly thermostable rigid-rod networks constructed from an unsymmetrical bisphthalonitrile bearing phthalazinone moieties[J]. Polym. Chem., 2012,3:1024-1032. doi: 10.1039/c2py00417h
24. [24]
  Q.L. Yan, J.Y. Wang, M.J. Wang. Novel poly(phthalazinone ether nitrile) insulating coating[J]. J. Funct. Mater., 2005,36:1347-1349.
25. [25]
  J.Y. Wang, M.J. Wang, C. Liu. Synthesis of poly(arylene ether nitrile ketone)s bearing phthalazinone moiety and their properties[J]. Polym. Bull., 2013,70:1467-1481. doi: 10.1007/s00289-012-0866-z
26. [26]
  A.H. Cook, D.G. Jones. Experiments in the triazine and the glyoxaline series[J]. J. Chem. Soc., (1941):278-282.
27. [27]
  D.R. Anderson, J.M. Holovka. Thermally resistant polymers containing the striazine ring[J]. J. Polym. Sci. A, 1966,4:1689-1702. doi: 10.1002/pol.1966.150040704
28. [28]
  Z.H. Weng, J.Y. Fu, L.S. Zong. Temperature for curing phthalonitrileterminated poly(phthalazinone ether nitrile) reduced by a mixed curing agent and its curing behavior[J]. RSC Adv., 2015,5:92055-92060. doi: 10.1039/C5RA17234A
29. [29]
  J.F. Ma, J. Yang, G.L. Zheng. A porous supramolecular architecture from a copper(Ⅱ) coordination polymer with a 3D four-connected 86 net[J]. Inorg. Chem., 2003,42:7531-7534. doi: 10.1021/ic034846q
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沈阳化工大学材料科学与工程学院沈阳 110142

Multiple-SO3H functioned ionic liquid as efficient curing agent for phthalonitrile-terminated poly(phthalazinone ether nitrile)

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通讯作者: 陈斌, bchen63@163.com

Multiple-SO₃H functioned ionic liquid as efficient curing agent for phthalonitrile-terminated poly(phthalazinone ether nitrile)