Advertisement

Polymer Bulletin

, Volume 75, Issue 3, pp 1037–1054 | Cite as

Phthalonitrile-functionalized poly(ether imide) oligomers derived from phthalazinone-containing dianhydride: facile synthesis, curing and properties

  • Cheng Liu
  • Encheng Lin
  • Lishuai Zong
  • Chengde Liu
  • Guipeng Yu
  • Jinyan Wang
  • Fangyuan Hu
  • Zhihuan Weng
  • Xigao Jian
Original Paper
  • 175 Downloads

Abstract

A novel series of soluble and curable poly(ether imide) oligomers (PPEI-Phs) containing phthalazinone moiety and terminal phthalonitrile groups were prepared from an excess amount of phthalazinone-based dianhydride and 4,4′-diaminodiphenyl ether, followed by being end-capped with 4-(3-aminophenoxy)phthalonitrile in a two-step, one-pot reaction. The phthalazinone-based PPEI-Phs were cured by a heating treatment procedure up to 350 °C, in the presence of 4,4′-diaminodiphenylsulfone to obtain the cross-linked polymers (cPPEI-Phs). Fourier transform infrared and elemental analysis was utilized to confirm the chemical structures of the resultant oligomers and cross-linked polymers. PPEI-Phs exhibited good solubility in polar aprotic solvents, such as N-methyl pyrrolidone, m-cresol and pyridine, partially soluble in N,N-dimethyl-2-acetamide and chloroform, while the cross-linked cPPEI-Phs were insoluble in all tested solvents, even in sulfuric acid. Furthermore, the gel content of the cPPEI-Phs samples ranged from 96 to 88%, which confirmed the formation of cross-linked network. PPEI-Phs showed high glass transition temperature (T g) ranged from 225 to 286 °C as determined by differential scanning calorimetry, however, no detectable T g was observed after thermal curing. cPPEI-Phs exhibited T d5% in the range of 529–545 °C, which is up to 49 °C higher than the PPEI-Phs, indicating the crosslinking structures of cPPEI-Phs. Moreover, all of cPPEI-Phs displayed high limited oxygen index up to 46.7, which can be attributed to the formation of N-heterocyclic s-triazine or phthalocyanine structures during the curing procedure.

Keywords

Poly(ether imide) 4-Phenyl phthalazinone Phthalonitrile oligomer Thermal property 

Notes

Acknowledgements

We acknowledge financial support from the Fundamental Research Funds for the Central Universities (DUT16LK14, DUT16RC(3)056), National Natural Science Foundation of China (No. 51503024, No. 51673033) and the National High Technology Research and Development Program (No. 2015AA033802).

References

  1. 1.
    Sastri SB, Keller TM (1999) Phthalonitrile polymers: cure behavior and properties. J Polym Sci Pol Chem 37:2105–2111CrossRefGoogle Scholar
  2. 2.
    Sastri SB, Armistead JP, Keller TM (1996) Phthalonitrile–Carbon Fiber Composites. Polym Compos 17:816–822CrossRefGoogle Scholar
  3. 3.
    Guo H, Zhan Y, Chen Z, Meng F, Wei J, Liu X (2013) Decoration of basalt fibers with hybrid Fe3O4 microspheres and their microwave absorption application in bisphthalonitrile composites. J Mater Chem A 1:2286–2296CrossRefGoogle Scholar
  4. 4.
    Selvakumar P, Sarojadevi M (2009) Development of oligomeric phthalonitrile resins for advanced composite applications. Macromol Symp 277:190–200CrossRefGoogle Scholar
  5. 5.
    Yuan K, Liu C, Han J, Yu G, Wang J, Duan H, Wang Z, Jian X (2016) Phthalazinone structure-based covalent triazine frameworks and their gas adsorption and separation properties. RSC Adv 6:12009–12020CrossRefGoogle Scholar
  6. 6.
    Taguchi Y, Yasumoto M, Tsuchiya T, Oishi A, Shibuya I (1993) A novel synthesis of 1,3,5-triazine derivative under high-pressure. Chem Lett 22:1097–1100CrossRefGoogle Scholar
  7. 7.
    Burchill PJ (1994) On the formation and properties of a high-temperature resin from a bisphthalonitrile. J Polym Sci Pol Chem 32:1–8CrossRefGoogle Scholar
  8. 8.
    Keller TM, Dominguez DD (2005) High temperature resorcinol-based phthalonitrile polymer. Polymer 46:4614–4618CrossRefGoogle Scholar
  9. 9.
    Xu MZ, Jia K, Liu XB (2015) Effect of bisphenol-A on the structures and properties of phthalonitrile-based resin containing benzoxazine. Express Polym Lett 9:567–581CrossRefGoogle Scholar
  10. 10.
    Cao GP, Chen WJ, Wei JJ, Li WT, Liu XB (2007) Synthesis and characterization of a novel bisphthalonitrile containing benzoxazine. Express Polym Lett 1:512–518CrossRefGoogle Scholar
  11. 11.
    Keller TM (1994) Synthesis and polymerization of multiple aromatic ether phthalonitriles. Chem Mater 6:302–305CrossRefGoogle Scholar
  12. 12.
    Xiong S, Fu X, Xiang L, Yu G, Guan J, Wang Z, Du Y, Xiong X, Pan C (2014) Liquid acid-catalysed fabrication of nanoporous 1,3,5-triazine frameworks with efficient and selective CO2 uptake. Polym Chem UK 5:3424–3431CrossRefGoogle Scholar
  13. 13.
    Weng Z, Fu J, Zong L, Liu C, Wang J, Jian X (2015) Temperature for curing phthalonitrile-terminated poly(phthalazinone ether nitrile) reduced by a mixed curing agent and its curing behavior. RSC Adv 5:92055–92060CrossRefGoogle Scholar
  14. 14.
    Ji S, Yuan P, Hu J, Sun R, Zeng K, Yang G (2016) A novel curing agent for phthalonitrile monomers: curing behaviors and properties of the polymer network. Polymer 84:365–370CrossRefGoogle Scholar
  15. 15.
    Zeng K, Zhou K, Zhou SH, Hong HB, Zhou HF, Wang YP, Miao PK, Yang G (2009) Studies on self-promoted cure behaviors of hydroxy-containing phthalonitrile model compounds. Eur Polym J 45:1328–1335CrossRefGoogle Scholar
  16. 16.
    Amir B, Zhou H, Liu F, Aurangzeb H (2010) Synthesis and characterization of self-catalyzed imide-containing phthalonitrile resins. J Polym Sci Pol Chem 48:5916–5920CrossRefGoogle Scholar
  17. 17.
    Guo H, Chen Z, Zhang J, Yang X, Zhao R, Liu X (2012) Self-promoted curing phthalonitrile with high glass transition temperature for advanced composites. J Polym Res 19:9918CrossRefGoogle Scholar
  18. 18.
    Hu J, Liu Y, Jiao Y, Ji S, Sun R, Yuan P, Zeng K, Pu X, Yang G (2015) Self-promoted phthalimide-containing phthalonitrile resins with sluggish curing process and excellent thermal stability. RSC Adv 5:16199–16206CrossRefGoogle Scholar
  19. 19.
    Du RH, Li WT, Liu XB (2009) Synthesis and thermal properties of bisphthalonitriles containing aromatic ether nitrile linkages. Polym Degrad Stab 94:2178–2183CrossRefGoogle Scholar
  20. 20.
    Laskoski M, Dominguez DD, Keller TM (2005) Synthesis and properties of a bisphenol A based phthalonitrile resin. J Polym Sci Pol Chem 43:4136–4143CrossRefGoogle Scholar
  21. 21.
    Zeng K, Hong HB, Zhou SH, Wu DM, Miao PK, Huang ZF, Yang G (2009) A new soluble aramide with pendant phthalonitrile units and polymer property enhancement by nitrile cure reactions. Polymer 50:5002–5006CrossRefGoogle Scholar
  22. 22.
    Zou X, Xu M, Jia K, Liu X (2014) Synthesis, polymerization, and properties of the allyl-functional phthalonitrile. J Appl Polym Sci 131:41203Google Scholar
  23. 23.
    Zhang Z, Li Z, Zhou H, Lin X, Zhao T, Zhang M, Xu C (2014) Self-catalyzed silicon-containing phthalonitrile resins with low melting point, excellent solubility and thermal stability. J Appl Polym Sci 131:40919Google Scholar
  24. 24.
    Zhong J, Jia K, Zhao R, Liu X (2010) Plasticization of poly(arylene ether nitrile) by the melt blending of phthalonitrile prepolymer: a rheological, mechanical, and thermal study. J Appl Polym Sci 116:2668–2673Google Scholar
  25. 25.
    Xi Z, Chen X, Yu X, Ma Y, Ji P, Naito K, Ding H, Qu X, Zhang Q (2016) Synthesis and properties of a novel high temperature pyridine-containing phthalonitrile polymer. J Polym Sci Pol Chem 54:3819–3825CrossRefGoogle Scholar
  26. 26.
    Laskoski M, Dominguez DD, Keller TM (2007) Synthesis and properties of aromatic ether phosphine oxide containing oligomeric phthalonitrile resins with improved oxidative stability. Polymer 48:6234–6240CrossRefGoogle Scholar
  27. 27.
    Selvakumar P, Padmini K, Sarojadevi M, Leelavathy MF (2010) Synthesis, characterization and thermal properties of imide-containing phthalonitrile polymers. J Macromol Sci Pure Appl Chem 47:76–88CrossRefGoogle Scholar
  28. 28.
    Wang J, Liu C, Su G, Jian X (2012) Synthesis and characterization of organo-soluble polyimides containing phthalazinone and bicarbazole moieties in the main chain. High Perform Polym 24:356–365CrossRefGoogle Scholar
  29. 29.
    Wang J, Liao G, Liu C, Jian X (2004) Poly(ether imide)s derived from phthalazinone-containing dianhydrides. J Polym Sci Pol Chem 42:6089–6097CrossRefGoogle Scholar
  30. 30.
    Yu G, Liu C, Zhou H, Wang J, Lin E, Jian X (2009) Synthesis and characterization of soluble copoly(arylene ether sulfone phenyl-s-triazine)s containing phthalazinone moieties in the main chain. Polymer 50:4520–4528CrossRefGoogle Scholar
  31. 31.
    Wang J, Wang M, Liu C, Zhou H, Jian X (2013) Synthesis of poly(arylene ether nitrile ketone)s bearing phthalazinone moiety and their properties. Polym Bull 70:1467–1481CrossRefGoogle Scholar
  32. 32.
    Yu G, Wang J, Liu C, Lin E, Jian X (2009) Soluble and curable poly(phthalazinone ether amide)s with terminal cyano groups and their crosslinking to heat resistant resin. Polymer 50:1700–1708CrossRefGoogle Scholar
  33. 33.
    Liu P, Wang J, Liu C, Jian X (2006) Lyotropic liquid crystalline polyamides containing aromatic, heterocyclic structures: preparation and properties. Macromol Chem Phys 207:1610–1615CrossRefGoogle Scholar
  34. 34.
    Liu C, Li X, Xu J, Jian X (2011) Synthesis and characterization of novel polybenzimidazoles containing 4-phenyl phthalazinone moiety. Eur Polym J 47:1852–1860CrossRefGoogle Scholar
  35. 35.
    Zong L, Liu C, Zhang S, Wang J, Jian X (2015) Enhanced thermal properties of phthalonitrile networks by cooperating phenyl-s-triazine moieties in backbones. Polymer 77:177–188CrossRefGoogle Scholar
  36. 36.
    Boyle ME, Adkins JD, Snow AW, Cozzens RF, Brady RF (1995) Synthesis and characterization of melt-polymerizable aminophthalocyanine monomers. J Appl Polym Sci 57:77–85CrossRefGoogle Scholar
  37. 37.
    Snow AW, Griffith JR, Marullo NP (1984) Syntheses and characterization of heteroatom-bridged metal-free phthalocyanine network polymers and model compounds. Macromolecules 17:1614–1624CrossRefGoogle Scholar
  38. 38.
    Zeng K, Li L, Xiang S, Zhou Y, Yang G (2012) Synthesis and thermal polymerization of new polyimides with pendant phthalonitrile units. Polym Bull 68:1879–1888CrossRefGoogle Scholar
  39. 39.
    Mushtaq N, Chen G, Sidra LR, Liu Y, Fang X (2016) Synthesis and crosslinking study of isomeric poly(thioether ether imide)s containing pendant nitrile and terminal phthalonitrile groups. Polym Chem UK 7:7427–7435CrossRefGoogle Scholar
  40. 40.
    Badshah A, Kessler MR, Heng Z, Hasan A (2014) Synthesis and characterization of phthalonitrile resins from ortho-linked aromatic and heterocyclic monomers. Polym Int 63:465–469CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2017

Authors and Affiliations

  1. 1.State Key Laboratory of Fine ChemicalsDalian University of TechnologyDalianPeople’s Republic of China
  2. 2.Department of Polymer Science and MaterialsDalian University of TechnologyDalianPeople’s Republic of China
  3. 3.Liaoning Province Engineering Center of High Performance ResinsDalianPeople’s Republic of China
  4. 4.College of Chemistry and Chemical EngineeringCentral South UniversityChangshaPeople’s Republic of China

Personalised recommendations