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Synthesis and characterization of polyimides from 4,4′-(3-(tert-butyl)-4-aminophenoxy)diphenyl ether

  • Congyan Li
  • Lang Yi
  • Shuting Xu
  • Xiuming Wu
  • Wei Huang
  • Deyue Yan
ORIGINAL PAPER

Abstract

A novel diamine 4,4′-(3-(tert-butyl)-4-aminophenoxy)diphenyl ether (4) was synthesized from 2-tert-butylaniline and 4,4′-oxydiphenol through iodination, acetyl protection, coupling reaction and deacetylation protection. Then some polyimides (PIs) were obtained by one-pot polycondensation of diamne 4 with several commercial aromatic dianhydrides respectively. They all exhibit enhanced solubility in organic solvents (such as NMP, DMF, THF and CHCl3 etc.) at room temperature. Their number-average molecular weights are in the range of (2.1–3.7) × 104 g/mol with PDI from 2.25 to 2.74 by GPC. They can form transparent, tough and flexible films by solution-casting. The light transparency of them is higher than 90% in the visible light range from 400 nm to 760 nm and the cut-off wavelengths of UV–vis absorption are below 370 nm. They also display the outstanding thermal stability with the 5% weight loss temperature from 525 °C to 529 °C in nitrogen atmosphere. The glass transition temperatures (T g s) are higher than 264 °C by DSC. XRD results demonstrate that these PIs are amorphous polymers with the lower water absorption (<0.66%). In summary, the incorporation of tert-butyl groups and multiple phenoxy units into the rigid PI backbones can endow them excellent solubility and transparency with relatively high T g s.

Keywords

tert-Butyl Multiple phenoxy units Polyimides Solubility Transparency 

Notes

Acknowledgements

The authors gratefully acknowledge the financial supports provided by the National Basic Research Program of China (No. 2014CB643604), Shanghai Key Projects of Basic Research (No. 16JC1403600).

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Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  • Congyan Li
    • 1
  • Lang Yi
    • 1
  • Shuting Xu
    • 1
  • Xiuming Wu
    • 1
  • Wei Huang
    • 1
  • Deyue Yan
    • 1
  1. 1.School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix CompositesShanghai Jiao Tong UniversityShanghaiPeople’s Republic of China

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