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


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.


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



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).


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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

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