Thermosetting oligoimides with phenylethynyl reactive groups

Gavrish A.V., Akhmadieva K.R., Shosheva A.L., Lavrin M.A.
UDC
544.122.2
DOI
10.18577/2307-6046-2023-0-9-41-56
Article PDF (Russian) (858.62 KB)
How to cite
Gavrish A.V., Akhmadieva K.R., Shosheva A.L., Lavrin M.A. Thermosetting oligoimides with phenylethynyl reactive groups // Proceedings of VIAM. 2023. No. 9. DOI: 10.18577/2307-6046-2023-0-9-41-56. URL: https://test.viam.ru/en/journal/2023/9/4
Keywords
imide oligomers, phenylethynyl groups, molecular weight, thermal stability, oligomer PETI-5
Abstract

A review of imide oligomers with phenylethynyl (PE) groups is presented. Physico-chemical properties of different oligomers are disclosed, new series of imide oligomers with phenylethynyl groups are described, thermal stability, glass transition temperatures (Tg) and curing temperatures are analyzed. The effect of molecular weight of PETI-5 oligomer on various properties is also presented.

Reference list
  1. Kablov E.N. Airospace materials science. Vse materialy. Entsiklopedicheskiy spravochnik, 2008, no. 3, pp. 2–14.
  2. Scola D.A. Polyimid Resins. ASM Handbook. ASM International, 2001, vol. 21: Composites, pp. 105–119.
  3. Zharinov M.A., Petrova A.P., Babchuk I.V., Akhmadieva K.R. Heat-resistant polyimide adhesives of structural purposes. Klei. Germetiki. Tekhnologii, 2021, no. 4, pp. 2–8.
  4. Kablov E.N., Chursova L.V., Babin A.N., Mukhametov R.R., Panina N.N. Development of the FSUE VIAM in the field of melt binders for polymer composite materials. Polimernye materialy i tekhnologii, 2016, vol. 2, no. 2, pp. 37–42.
  5. Connell J.W., Smith J.G., Hergenrother P.M. Oligomers and Polymers Containing Phenylethynyl Groups. Journal of Macromolecular Science Part C: Polymer Reviews, 2000, vol. 40, no. 2, рр. 207–230.
  6. Jensen B.J., Bryant R.G., Smit J.G., Hergenrother P.M. Adhesive Properties of Cured Phenylethynyl-Terminated imide Oligomers. Journal Adhesion, 1994, vol. 54, pp. 57–66.
  7. Vannucci R. Non-MDA Polyimides. High Temple Workshop, 1995, vol. 15, pp. 16–19.
  8. Chuang K.C., Kinder J.D., Hull D.L., Rigid-Rod Polyimides Based on Noncoplanar 4,4ʹ-Biphenylenediamines: A Review of Diamines. Macromolecules, 1997, vol. 30, no. 23, pp. 7183–7190.
  9. Gray R. Resin Transfer Molding of High Temperature Composites. High Temple Workshop, 1998, vol. 17, рр. 20–22.
  10. Smith J.G., Connell J.W., Hergenrother P.M. The Effect of Phenylethynyl Terminated Imide Oligomer Molecular Weight on the Properties of Composites. Journal Composite Materials, 2000, vol. 34, no. 7, рр. 614–627.
  11. Wright M.E., Schorzman D.A., Pence L.E. Thermally Curing Aryl−Ethynyl End-Capped Imide Oligomers: Study of New Aromatic End Caps. Macromolecules, 2000, vol. 33, no. 15, рр. 8611–8617.
  12. Mukhametov R.R., Petrova A.P. Thermosetting binders for polymer composites (review). Aviacionnye materialy i tehnologii, 2019, no. 3 (56), pp. 48–58. DOI: 10.18577/2071-9140-2019-0-3-48-58.
  13. Kablov E.N., Laptev A.B., Prokopenko A.N., Gulyaev A.I. Relaxation of polymeric composite materials under the prolonged action of static load and climate (review). Part 1. Binders. Aviation materials and technologies, 2021, no. 4 (65), paper no. 08. Available at: http://www.journal.viam.ru (accessed: May 01, 2023). DOI: 10.18577/2071-9140-2021-0-4-70-80.
  14. Hong W., Yuan L., Ma Y. Resin Transfer Moldable Fluorinated Phenylethynyl-Terminated Imide Oligomers with High Tg: Structure–Melt Stability Relationship. Journal Polymers, 2021, vol. 13, p. 903.
  15. Cano R.J., Jensen B.J. Effect of Molecu ar Weight on Processing and Adhesive Properties of the Phenylethynyl-Terminated Polyimide LARCTM-PETI-5. Journal Adhesion, 1997, vol. 60, рр. 113–123.
  16. Kurnosov A.O., Petrova A.P., Slavin A.V., Vavilova M.I., Kurshev Е.V. Comparison of the properties of glass-reinforced plastics based on polyimide binders of solution and melt type. Trudy VIAM, 2022, no. 10 (116), paper no. 04. Available at: http://www.viam-works.ru (accessed: May 03, 2023). DOI: 10.18577/2307-6046-2022-0-10-42-54.
  17. Gunyaeva A.G., Kurnosov A.O., Gulyaev I.N. High-temperature polymer composite materials developed FSUE «VIAM» for aerospace engineering: past, present and future (review). Trudy VIAM, 2021, no. 1 (95), paper no. 05. Available at: http://www.viam-works.ru (accessed: May 10, 2023). DOI: 10.18577/2307-6046-2021-0-1-43-53.
  18. Johnston J.A., Li F.M., Harris F.W. Synthesis and characterization of imide oligomers end-capped with 4-(phenylethynyl) phthalic anhydrides. Journal Polymer, 1994, vol. 35, no. 22, pp. 4865–4873.
  19. Su C.-N., Ji M., Fan L., Yang S.-Y. Phenylethynyl-endcapped oligomides with low melt viscosities and high Tg: Effects of the molecular weights. High Performance Polymers, 2011, vol. 23, p. 352–361.
  20. Meyer G.W., Glass T.E., Grubs H.J., McGrath J.E. Synthesis and Characterization of Polyimides Endcapped with Phenylethynylphthalic Anhydride. Journal of Polymer Science, 1995, vol. 33, p. 2141–2149.
  21. Jensen B.J., Bryant R.G., Hergenrother P.M. Chemistry and properties of a phenylethynyl terminated polyimide. Journal of applied polymer science, 1996, vol. 59, no. 8, pp. 1249–1254.
  22. Thermally stable, highly fused quinoxaline composition and method of synthesis: pat. US 3876614A; appl. 17.04.74; publ. 08.04.75.
  23. Hergenrother P.M. Acetylene Terminated Phenyl-as-triazine Oligomers and Polymers. Macromolecules, 1978, vol. 11, pp. 332–339.
  24. Jensen B.J., Chang A.C. Synthesis and Characterization of Modified Phenylethynyl Imides. High Performance Polymers, 1998, vol. 10, no. 2, pp. 168–175.
  25. Connell J.W., Smith J.G., Hergenrother P.M., Rommel M.L. Neat resin, adhesive and composite properties of reactive additive/PETI-5 blends. Journal High Performance Polymers, 2000, vol. 12, pp. 323–333.
  26. Cano R.J., Jensen B.J. Out of the Autoclave Fabrication of LaRC™ PETI-9 Polyimide Laminates, NASA Langley Research Center Hampton. Materials Science, 2013, vol. 10, pp. 56–68.
  27. Hou T.H., Cano R.J., Jensen B.J. IM7/LaRC™ MPEI-1 polyimide composites. High Performance Polymers, 1998, vol. 10, no. 2, pp. 181–183.
  28. Kolpachkov E.D., Kurnosov A.O., Papina S.N., Petrova A.P. Specificity of the formation of fiberglass based on PMR-polyimides. Trudy VIAM, 2022, no. 6 (112), paper no. 04. Available at: http://www.viam-works.ru (accessed: May 12, 2023) DOI: 10.18577/2307-6046-2022-0-7-37-49.
  29. Pryde C.A. Effects of Chemical and Physical Changes During Cure. Journal Polymer Science. Part A: Polymer Chemistry, 1989, vol. 27, pp. 711.
  30. Rommel M.L., Connell J., Hergenrother P.M. Neat Resin, Adhesive and Composite Properties of Reactive Additive/PETI-5 Blends. Materials Science, 2000, vol. 23, pp. 104–109.
  31. Connell J.W., Smith J.G., Hergenrother P.M. Properties of Imide Oligomers Containing Pendent Phenylethynyl Groups. Journal Adhesion, 1997, vol. 60, no. 15, pp. 12–22.
  32. Ghose S., Cano R.J., Watson K.A. High temperature VARTM of phenylethynyl terminated imides. High Performance Polymers, 2009, vol. 21, no. 5, pp. 648–653.
  33. Connell J.W., Smith J.G., Hergenrother P.M. High Temperature Transfer Molding Resins: Status of PETI-298 and PETI-330. Journal Technologies, Inc. Marietta, 2003, vol. 21, no. 2, pp. 10–15.
  34. Hergenrother P.M. Phenylethynyl terminated imide oligomer. Encyclopedia of Polymer Science and Engineering, 1988, vol. 1, p. 61.
  35. Hergenrother P.M., Bryant R.G., Jensen B.J., Havens S.J. Phenylethynyl-terminated imide oligomers and polymers therefrom. Journal Polymer Science. Part A: Polymer Chemistry, 1994, vol. 32, pp. 3061.
  36. Smith J.G., Connell J.W., Hergenrother P.M. Polyimides from 2,3,3′,4′-biphenyltetracarboxylic dianhydride and aromatic diamines. Journal Composite Materials, 2002, vol. 36, no. 19, pp. 2250–2255.
  37. Hergenrother P.M., Smith J.G. Chemistry and properties of imide oligomers end-capped with phenylethynylphthalic anhydrides. Journal Polymer, 1994, vol. 35, pp. 4857–4864.
  38. Valueva M.I., Zelenina I.V., Nacharkina A.V., Ahmadieva K.R. Technological features of obtaining high temperature polyimide carbons. Foreign experience (review). Trudy VIAM, 2022, no. 6 (112), paper no. 08. Available at: http://www.viam-works.ru (accessed: May 15, 2023). DOI: 10.18577/2307-6046-2022-0-6-80-95.
  39. Tsampas S., Fernberg P., Joffe R. Development of novel high Tg polyimide-based composites. Part 2: Mechanical characterization. Journal of Composite Materials, 2018, vol. 52, no. 2, pp. 261–274.
  40. Zrida H., Fernberg P., Ayadi Z. Microcracking in thermally cycled and aged Carbon fibrepolyimide laminates. International Journal of Fatigue, 2016, vol. 23, no. 12, pp. 26–32.