Skip to main content
Log in

Coating properties of 1H,1H-perfluorooctylamine-terminated polyimides based on hexafluoroisopropylidene diphthalic anhydride and 1,4,5,8 naphthalenetetracarboxylic dianhydride

  • Published:
Journal of Coatings Technology and Research Aims and scope Submit manuscript

Abstract

This study attempted to prepare polyimide coatings (PIs) containing 6FDA (hexafluoroisopropylidene diphthalic anhydride) and/or NTDA (1,4,5,8 naphthalenetetracarboxylic dianhydride) in various ratios. 1% of these polyimide chains were terminated with 1H,1H-perfluorooctylamine (PFOA) and PFOA, and terminated polyimide coatings (PIFs) were prepared in the same ratios as PIs. Coatings were produced on aluminum substrates by a 75-μm wire-wound applicator and thermally imidized. Finally, thermal, wear, and physical properties of PIFs and PIs were compared to each other. PIFs exhibited higher abrasion resistance than PIs due to the presence of PFOA. The increase in 6FDA content also resulted in elevated abrasion resistance. Both NTDA and 6FDA compounds improved thermal stability. The increase in NTDA content raised the Tg values of the polyimides. PIFs exhibited higher static water contact angle values than PIs, but the existence of microcracks decreased their hydrophobicity. The gloss values of PIFs were excellent. Improved values were obtained for pencil hardness, crosscut adhesion, and MEK (methyl ethyl ketone) rubbing properties for all coatings. In addition to the pencil hardness test, a pendulum hardness test was also carried out. The presence of PFOA affected pendulum hardness values positively, and the increase in the amount of 6FDA on polymer backbone improved the pendulum hardness values despite the rigidity of NTDA.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Mushtaq, N, Chen, G, Sidra, LR, Fang, X, “Organosoluble and High Tg Polyimides from Asymmetric Diamines Containing N-Amino and N-Aminophenyl Naphthalimide Moieties.” RSC Adv., 6 25302–25310 (2016)

    Article  Google Scholar 

  2. Eichstadt, AE, Ward, TC, Bagwell, MD, Farr, IV, Dunson, DL, McGrath, JE, “Synthesis and Characterization of Amorphous Partially Aliphatic Polyimide Copolymers Based on Bisphenol-A Dianhydride.” Macromolecules, 35 7561–7568 (2002)

    Article  Google Scholar 

  3. Tsai, MH, Liu, SJ, Chiang, PC, “Synthesis and Characteristics of Polyimide/Titania Nano Hybrid Films.” Thin Solid Films, 515 1126–1131 (2006)

    Article  Google Scholar 

  4. Cho, YJ, Park, HB, “High Performance Polyimide with High Internal Free Volume Elements.” Macromol. Rapid Commun., 32 579–586 (2011)

    Article  Google Scholar 

  5. Yu, YY, Chien, WC, Wu, TH, Yu, HH, “Highly Transparent Polyimide/Nanocrystalline-Titania Hybrid Optical Materials for Antireflective Applications.” Thin Solid Films, 520 1495–1502 (2011)

    Article  Google Scholar 

  6. Chisca, S, Musteata, VE, Stoica, I, Sava, I, Bruma, M, “Effect of the Chemical Structure of Aromatic-Cycloaliphatic Copolyimide Films on Their Surface Morphology, Relaxation Behavior and Dielectric Properties.” J. Polym. Res., 20 111 (2013)

    Article  Google Scholar 

  7. Varganici, CD, Rosu, D, Barbu-Mic, C, Rosu, L, Popovici, D, Hulubei, C, Simionescu, BC, “On the Thermal Stability of Some Aromatic-Aliphatic Polyimides.” J. Anal. Appl. Pyrolysis, 113 390–401 (2015)

    Article  Google Scholar 

  8. Bakar, E, “Synthesis of the Some Fluorine Polymers and the Investigation of Surface Coating Properties”, pp. 1–28. M.S. thesis, The Graduate School of Natural and Applied Science of Selcuk University, Konya (2013)

  9. Jeong, KU, Kim, JJ, Yoon, TH, “Synthesis and Characterization of Novel Polyimide Containing Fluorine and Phosphine Oxide Moieties.” Polymer, 42 6019–6030 (2001)

    Article  Google Scholar 

  10. Oğultürk, G, “Improving the Water Repellency and Wrinkle Recovery Properties of the Woven Fabrics with One Step,” pp. 49–60. M.S. thesis, Department of Polymer Science and Technology Polymer Science and Technology Programme, Istanbul Technical University, Istanbul (2008)

  11. Tao, L, Yang, H, Liu, J, Fan, L, Yang, S, “Synthesis and Characterization of Highly Optical Transparent and Low Dielectric Constant Fluorinated Polyimides.” Polymer, 50 6009–6018 (2009)

    Article  Google Scholar 

  12. Yanga, JW, Wang, CS, “Novel Perfluorononenyloxy Group-Containing Polyimides.” Polymer, 40 1411–1419 (1999)

    Article  Google Scholar 

  13. Yang, CY, Chen, JS, Hsu, SL-C, “Effects of O2 and N2 Plasma Treatment on 6FDA-BisAAF Fluorine-Contained Polyimide.” J. Electrochem. Soc., 153 (6) F120–F125 (2006)

    Article  Google Scholar 

  14. Hsu, SL-C, Luo, G-W, Chen, H-T, Chuang, S-W, “Synthesis and Characterization of Novel Aromatic Poly (Imide-Benzoxazole) Copolymers.” J. Polym. Sci. Part A Polym. Chem, 43 6020–6027 (2005)

    Article  Google Scholar 

  15. Chang, HC, Chang, SL, Lin, CH, Chen, SW, “Design and Synthesis of Unsymmetric Phosphinated Diamines for High-Tg, Transparent Polyimides.” Polymer, 53 1651–1658 (2012)

    Article  Google Scholar 

  16. Yeo, H, Goh, M, Ku, BC, You, NH, “Synthesis and Characterization of Highly-Fluorinated Colorless Polyimides Derived from 4,40-((Perfluoro-[1,10-Biphenyl]-4,40-diyl) Bis(oxy))Bis(2,6-Dimethylaniline) and Aromatic Dianhydrides.” Polymer, 76 280–286 (2015)

    Article  Google Scholar 

  17. Feger, C, Franke, H, “Polyimides in High-Performance Electronics Packaging and Optoelectronic Applications.” In: Ghosh, MK, Mittal, KL (eds) Polyamides Fundamentals and Applications, pp. 759–814. Marcel Dekker, New York (1996)

  18. Yang, C-P, Su, Y-Y, Guo, W, Hsiao, S-H, “Synthesis and Properties of Novel Fluorinated Polynaphthalimides Derived from 1,4,5,8-Naphthalenetetracarboxylic Dianhydride and Trifluoromethyl-Substituted Aromatic bis(ether amine)s.” Eur. Polym. J., 45 721–729 (2009)

    Article  Google Scholar 

  19. Ishii, J, Yokoyama, N, Hasegawa, M, “Solution-Processable CF3-Substituted Ductile Polyimides with Low Coefficients of Thermal Expansion as Novel Coating-Type Protective Layers in Flexible Printed Circuit Boards.” Prog. Org. Coat., 99 125–133 (2016)

    Article  Google Scholar 

  20. Er, ÖO, “Synthesis of Copolyimides Containing 6FDA,” pp. 40–62. M.S. thesis, The Graduate School of Science Engineering and Technology, Istanbul Technical University, Istanbul (2006)

  21. Tang, W, Huang, Y, Meng, W, Qing, F-L, “Synthesis of Fluorinated Hyperbranched Polymers Capable as Highly Hydrophobic and Oleophobic Coating Materials.” Eur. Polym. J., 46 506–518 (2010)

    Article  Google Scholar 

  22. Uyanik, M, Arpac, E, Schmidt, H, Akarsu, M, Sayilkan, F, Sayilkan, H, “Heat-Resistant Hydrophobic-Oleophobic Coatings.” J. Appl. Polym. Sci., 100 2386–2392 (2006)

    Article  Google Scholar 

  23. Kahraman, MV, Bayramoglu, G, Boztoprak, Y, Gungor, A, Kayaman-Apohan, N, “Synthesis of Fluorinated/Methacrylated Epoxy Based Oligomers and Investigation of its Performance in the UV Curable Hybrid Coatings.” Prog. Org. Coat., 66 52–58 (2009)

    Article  Google Scholar 

  24. Kahraman, MV, Akdemir, ZS, Kartal, I, Kayaman-Apohan, N, Gungor, A, “Preparation of Fluorine-Containing Hybrid Coatings: Investigation of Coating Performance onto ABS and PMMA Substrates.” Polym. Adv. Technol., 22 981–986 (2011)

    Article  Google Scholar 

  25. Çakmakçı, E, Güngör, A, Gören, AC, “Fluorine and Phosphine Oxide Containing Homo and Copolyimides.” J. Fluor. Chem., 186 66–78 (2016)

    Article  Google Scholar 

  26. Leu, T-S, Wang, C-S, “Synthesis and Properties of Copolyimides Containing Naphthalene Group.” Polymer, 43 7069–7074 (2002)

    Article  Google Scholar 

  27. ur Rehman, S, Li, P, Zhou, HW, Zhao, XG, Dang, GD, Chen, CH, “Thermally and Hydrolytically Stable Polyimides Containing Naphthalimide Units.” Polym. Degrad. Stab., 97 1581–1588 (2012)

    Article  Google Scholar 

  28. Tao, L, Yang, H, Liu, J, Fan, L, Yang, S, “Fluorinated Polybenzimidazopyrrolones with Excellent Alkaline-Hydrolysis Resistance.” J. Appl. Polym. Sci., 131 40041 (2014)

    Google Scholar 

  29. Shundrina, IK, Vaganova, TA, Kusov, SZ, Rodionov, VI, Karpova, EV, Koval, VV, Gerasimova, YV, Malykhin, EV, “Synthesis and Characterization of Polyimides Based on Novel Isomeric Perfluorinated Naphthylenediamines.” J. Fluor. Chem., 130 733–741 (2009)

    Article  Google Scholar 

  30. Jang, J, Lee, KJ, Kim, Y, “Fabrication of Polyimide Nanotubes and Carbon Nanotubes Containing Magnetic Iron Oxide in Confinement.” Chem. Commun., 30 3847–3849 (2005)

    Article  Google Scholar 

  31. Liu, J, Wang, K, Lin, L, Liu, R, Xie, Y, Gao, F, Liu, X, “Synthesis and Property of Fluorinated Polyimides with Double Bond End Groups for UV-Cured Coating.” Prog. Org. Coat., 99 103–109 (2016)

    Article  Google Scholar 

  32. Law, K-Y, “Definitions for Hydrophilicity, Hydrophobicity, and Superhydrophobicity: Getting the Basics Right.” J. Phys. Chem. Lett., 5 (4) 686–688 (2014)

    Article  Google Scholar 

  33. Watanabe, Y, Shibasaki, Y, Ando, S, Ueda, M, “Synthesis and Characterization of Novel Low-k Polyimides from Aromatic Dianhydrides and Aromatic Diamine Containing Phenylene Ether and Perfluorobiphenyl Units.” Polym. J., 38 79–84 (2006)

    Article  Google Scholar 

  34. Kizilkaya, C, Karatas, S, Apohan, N-K, Gungor, A, “Synthesis and Characterization of Novel Polyimide/SiO2 Nanocomposite Materials Containing Phenylphosphine Oxide via Sol-Gel Technique.” J. Appl. Polym. Sci., 115 3256–3264 (2010)

    Article  Google Scholar 

  35. Karatas, S, Kayaman-Apohan, N, Demirer, H, Gungor, A, “Polyimide-Silica Hybrid Coatings: Morphological, Mechanical, and Thermal Investigations.” Polym. Adv. Technol., 18 490–496 (2007)

    Article  Google Scholar 

  36. Marmur, A, “A Guide to the Equilibrium Contact Angles Maze.” In: Mittal, KL (ed.) Contact Angle, Wettability and Adhesion Principles and Applications, pp. 2–12. CRC Press (Taylor and Francis Group) and Leiden, Boca Raton and Leiden (2009)

    Google Scholar 

  37. Garratt, JR, “Transfer Characteristics for a Heterogeneous Surface of Large Aerodynamic Roughness.” Q. J. R. Meteorol. Soc., 104 491–502 (1978)

    Article  Google Scholar 

  38. Fox, PG, Freeman, IB, “What Does the Pendulum Hardness Test Measure?” J. Mater. Sci., 14 151–158 (1979)

    Article  Google Scholar 

Download references

Acknowledgments

This study was supported by Marmara University, Commission of Scientific Research Project under Grant FEN-C-YLP-100216-0052.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Emre Akin.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Çakir, M., Akin, E. & Artir, R. Coating properties of 1H,1H-perfluorooctylamine-terminated polyimides based on hexafluoroisopropylidene diphthalic anhydride and 1,4,5,8 naphthalenetetracarboxylic dianhydride. J Coat Technol Res 16, 699–710 (2019). https://doi.org/10.1007/s11998-018-0147-3

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11998-018-0147-3

Keywords

Navigation