Citation: Jing-Zhi Ma, Kang Cheng, Jiang-Bo Lv, Chang Chen, Jiang-Huai Hu, Ke Zeng, Gang Yang. Phthalonitrile-PPO Blends: Cure Behavior and Properties[J]. Chinese Journal of Polymer Science, ;2018, 36(4): 497-504. doi: 10.1007/s10118-018-2026-x shu

Phthalonitrile-PPO Blends: Cure Behavior and Properties

State Key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China

Corresponding author: Ke Zeng, zk_ican@sina.com Gang Yang, yanggang65420@163.com
Received Date: 6 July 2017
Accepted Date: 26 August 2017
Available Online: 16 November 2017

Hydroxy-containing low molecular weight poly(2,6-dimethyl-1,4-phenylene oxide) (rPPO) and self-promoted hydroxy-containing phthalonitrile (HPPH) were prepared by redistribution reaction and the simple nucleophilic displacement of a nitro-substituent from 4-nitrophthalonitrile in a dipolar aprotic solvent respectively. The hydroxy-containing phthalonitriles modified by rPPO were prepared by mechanical blending without compatibilizer, followed by heating. The curing behavior was studied using dynamic rheological analysis, and the results showed that the rPPO-modified phthalonitrile exhibited a large processing window (over -67℃) and complex viscosity (0.18-0.8 Pa·s) at moderate temperatures. After curing at 300℃, the resulting polymers showed good thermal stability and high modulus as observed by thermogravimetric analysis (TGA) and dynamic mechanical analysis (DMA). The dielectric properties and the morphology of rPPO-modified phthalonitrile networks were studied by dielectric analysis and field-emission scanning electron microscopy (SEM).
- Low molecular weight PPO,
- Phthalonitrile,
- Curing behavior,
- Dielectric properties
1. [1]
  Seike Y., Okude Y., Iwakura I., Chiba I., Ikeno. T.; Yamada T.. Synthesis of polyphenylene ether derivatives:estimation of their dielectric constants[J]. Macromol. Chem. Phys., 2003,204(15):1876-1881. doi: 10.1002/(ISSN)1521-3935
2. [2]
  Liang G. Z., Meng J., Zhao L.. Synthesis of styrene-maleic anhydride random copolymer and its compatibilization to poly(2,6-dimethyl-1,4-phenylene ether)/brominated epoxy resin[J]. Polym. Int., 2010,52(6):966-972.
3. [3]
  Hwang H. J., Hsu S. W., Wang C. S.. Synthesis and physical properties of low-molecular-weight redistributed poly(2,6-dimethyl-1,4-phenylene oxide) for epoxy resin[J]. J. Appl. Polym. Sci., 2008,110(3):1880-1890. doi: 10.1002/app.v110:3
4. [4]
  Su C. T., Lin K. Y., Lee T. J., Liang , M .. Preparation, characterization and curing properties of epoxy-terminated poly(alkyl-phenylene oxide)s[J]. Eur. Polym. J., 2010,46(7):1488-1497. doi: 10.1016/j.eurpolymj.2010.04.016
5. [5]
  Ishii Y., Ryan A. J.. Processing of poly(2,6-dimethyl-1, 4-phenylene ether) with epoxy resin[J]. 1. Reaction-induced phase separation. Macromolecules, 2000,33(1):158-166.
6. [6]
  Zeng K., Zhou K., Zhou S. H., Hong H. B., Zhou H. F., Wang Y. P., Miao P. K., Yang G.. Studies on self-promoted cure behaviors of hydroxy-containing phthalonitrile model compounds[J]. Eur. Polym. J., 2009,45(4):1328-1335. doi: 10.1016/j.eurpolymj.2008.12.036
7. [7]
  Laskoski M., Dominguez D. D., Keller T. M.. Synthesis and properties of a bisphenol A based phthalonitrile resin[J]. J. Polym. Sci., Part A:Polym. Chem., 2005,43(18):4136-4143. doi: 10.1002/(ISSN)1099-0518
8. [8]
  Dominguez D. D., Keller T. M.. Phthalonitrile-epoxy blends:cure behavior and copolymer properties[J]. J. Appl. Polym. Sci., 2010,110(4):2504-2515.
9. [9]
  Sastri S. B., Keller T. M.. Phthalonitrile polymers:cure behavior and properties[J]. J. Polym. Sci., Part A:Polym. Chem., 1999,37(13):2105-2111. doi: 10.1002/(ISSN)1099-0518
10. [10]
  Augustine D., Mathew D., Nair C. P. R.. Phenol-containing phthalonitrile polymers-synthesis, cure characteristics and laminate properties[J]. Polym. Int., 2013,62(7):1068-1076.
11. [11]
  Lv J. B., Ma J. Z., Cheng K., Chen C., Hu J. H., Zeng K., Yang G.. Insights into phthalonitrile/epoxy blends modification system from non-competitive cure system based on alicyclic anhydride[J]. Chinese J. Polym. Sci., 2017,35(12):1561-1571. doi: 10.1007/s10118-017-1992-8
12. [12]
  Zhou H., Badashah A., L uo, Z. H., Liu F., Zhao T.. Preparation and property comparison of ortho, meta, and para autocatalytic phthalonitrile compounds with amino group[J]. Polym. Adv. Technol., 2011,22(10):1459-1465. doi: 10.1002/pat.v22.10
13. [13]
  Laskoski M., Dominguez , D. D. Keller T. M.. Synthesis and properties of aromatic ether phosphine oxide containing oligomeric phthalonitrile resins with improved oxidative stability[J]. Polymer, 2007,48(21):6234-6240. doi: 10.1016/j.polymer.2007.08.028
14. [14]
  Sastri S. B., Armistead J. P., Keller T. M.. Phthalonitrile-carbon fiber composites[J]. Polym. Compos., 1996,17(6):816-822. doi: 10.1002/(ISSN)1548-0569
15. [15]
  Sastri S. B., Armistead J. P., Keller T. M.. Phthalonitrile-glass fabric composites[J]. Polym. Compos., 1997,18(1):48-54. doi: 10.1002/(ISSN)1548-0569
16. [16]
  Dominguez D. D., Jones H. N., Keller T. M.. The effect of curing additive on the mechanical properties of phthalonitrile-carbon fiber composites[J]. Polym. Compos., 2004,25(5):554-561. doi: 10.1002/(ISSN)1548-0569
17. [17]
  Keller T. M., Price T. R.. Amine-cured bisphenol-linked phthalonitrile resins[J]. J. Macromol. Sci. Chem., 1982,18(6):931-937. doi: 10.1080/00222338208077208
18. [18]
  Burchill P. J.. On the formation and properties of a high-temperature resin from a bisphthalonitrile[J]. J. Polym. Sci., Part A:Polym. Chem., 1994,32(1):1-8. doi: 10.1002/pola.1994.080320101
19. [19]
  Keller T. M., Griffith J. R.. The synthesis of a new class of polyphthalocyanine resins[J]. J. Am. Chem. Soc., 1980,132:25-34.
20. [20]
  Walton T. R., Griffith J. R., O'Rear J. G.. Adhesion science and technology[J]. J. Adhes. Sci. Technol., 1975,9:665-676.
21. [21]
  Yuan P., Ji S. C., Hu J. H., Hu X. P., Zeng K., Yang G.. Systematic study on highly efficient thermal synergistic polymerization effect between alicyclic imide moiety and phthalonitrile:scope, properties and mechanism[J]. Polymer, 2016,102:266-280. doi: 10.1016/j.polymer.2016.09.025
22. [22]
  Ji S. C., Yuan P., Hu J. H., Sun R., Zeng K., Yang G.. A novel curing agent for phthalonitrile monomers:Curing behaviors and properties of the polymer network[J]. Polymer, 2016,84:365-370. doi: 10.1016/j.polymer.2016.01.006
23. [23]
  Hu J. H., Wu D. M., Lu D. K., Xiang S. R., Zhao Y. C., Zeng K., Yang G.. Study on thermal behaviors of a novel cruciform amide-containing phthalonitrile monomer[J]. Des. Monomers Polym., 2015,18(7):620-626. doi: 10.1080/15685551.2015.1045331
24. [24]
  Hu J. H., Liu Y. C., Jiao Y., Ji S. C., Sun R., Yuan P., Zeng K., Pu X. M., Yang G.. Self-promoted phthalimide-containing phthalonitrile resins with sluggish curing process and excellent thermal stability[J]. RSC Adv., 2015,5(21):16199-16206. doi: 10.1039/C4RA17306F
25. [25]
  Wu D. M., Zhao Y. C., Zeng K., Yang G.. A novel benzimidazole-containing phthalonitrile monomer with unique polymerization behavior[J]. J. Polymr. Sci., Part A:Polym. Chem., 2012,50(23):4977-4982. doi: 10.1002/pola.v50.23
26. [26]
  Sastri S. B., Keller T. M.. Phthalonitrile cure reaction with aromatic diamines[J]. J. Polym. Sci., Part A:Polym. Chem., 1998,36(11):1885-1890. doi: 10.1002/(ISSN)1099-0518
27. [27]
  Zeng K., Zhou K., Tang W. R., Tang Y., Zhou H. F., Liu T., Wang Y. P., Zhou H. B., Yang G.. Synthesis and curing of a novel amino-containing phthalonitrile derivative[J]. Chinese Chem. Lett., 2007,18(5):523-526. doi: 10.1016/j.cclet.2007.03.035
28. [28]
  Laskoski M., Keller T. M., Ricks-Laskoski H. L., Giller C. B., Hervey J.. Improved synthesis of oligomeric sulfone-based phthalonitriles[J]. Macromol. Chem. Phys., 2015,216(17):1808-1815. doi: 10.1002/macp.201500198
29. [29]
  Kaliavaradhan K., Muthusamy S.. Synthesis and characterization of various phenylene diamine-based bismaleimide-containing phthalonitrile resins[J]. Polym. Bull., 2016,7(73):1921-1938.
30. [30]
  Wang J. B., Hu J. H., Zeng K., Yang G.. Preparation of self-promoted hydroxy-containing phthalonitrile resins by an in situ reaction[J]. RSC Adv., 2015,5(127):105038-105046. doi: 10.1039/C5RA18472J
31. [31]
  Bolon D. A.. Free-radical redistribution of phenol dimers[J]. J. Org. Chem., 1967,32(5):1584-1590. doi: 10.1021/jo01280a063
32. [32]
  Aert H. A. M. V., Genderen M. H. P. V., Steenpaal G. J. M. L. V., Nelissen L., Meijer , E. W.. Modified poly(2,6-dimethyl-1,4-phenylene ether)s prepared by redistribution[J]. Macromolecules, 1997,30(20):6056-6066. doi: 10.1021/ma970388r
33. [33]
  Baesjou P. J., Driessen W. L., Challa G., Reedijk J.. A kinetic and spectroscopic study on the copper catalyzed oxidative coupling polymerization of 2,6-dimethylphenol.X-ray structure of the catalyst precursor tetrakis (N-methylimidazole) bis(nitrato) copper(Ⅱ)[J]. J. Mol. Catal. A-Chem., 1996,110(3):195-210. doi: 10.1016/1381-1169(96)00065-9
34. [34]
  Hay A. S.. Polymerization by oxidative coupling:discovery and commercialization of PPO and noryl resins[J]. J. Polym. Sci., Part A:Polym. Chem., 1998,36(4):505-517. doi: 10.1002/(ISSN)1099-0518
35. [35]
  Viersen F. J., Challa G., Reedijk J.. Mechanistic studies of the oxidative coupling polymerization of 2,6-dimethylphenol:4.Mechanism of polymer formation catalysed by a copper(Ⅱ)-tmed complex[J]. Polymer, 1990,31(7):1368-1373. doi: 10.1016/0032-3861(90)90232-N
36. [36]
  Scoponi M., Pradella F., Kaczmarek H., Amadelli R., Carassiti V.. A reappraisal of the photo-oxidation mechanism at short and long wavelengths for poly(2,6-dimethyl-1,4-phenylene oxide)[J]. Polymer, 1996,37(6):903-916. doi: 10.1016/0032-3861(96)87272-7
37. [37]
  Li X. G.. High-resolution thermogravimetry of poly(2, 6-dimethyl-1,4-phenylene oxide)[J]. J. App. Polym. Sci., 1999,71(11):1887-1892. doi: 10.1002/(ISSN)1097-4628
38. [38]
  Blanco I., Cicala G., Latteri A., Mamo A., Recca A.. Thermal and thermo-oxidative degradations of poly (2,6-dimethyl-1,4-phenylene oxide) (PPO)/copoly(aryl ether sulfone) P(ESES-co-EES) block copolymers:a kinetic study[J]. J. Therm. Anal. Calorim., 2013,112(1):375-381. doi: 10.1007/s10973-012-2793-5
39. [39]
  Saron C., Sanchez E., Isabel Felisberti M.. Thermal and photochemical degradation of PPO/HIPS blends[J]. J. Appl. Polym. Sci., 2007,104(5):3269-3276. doi: 10.1002/(ISSN)1097-4628
40. [40]
  Saron C., Felisberti M. I.. Dynamic mechanical spectroscopy applied to study the thermal and photodegradation of poly(2,6-dimethyl-1,4-phenylene oxide)/high impact polystyrene blends[J]. Mat. Sci. Eng. A, 2004,370(1):293-301.
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