Bismaleimide resins (review)

Part 1
Shosheva A.L.
Shosheva A.L. Bismaleimide resins (review). Part 1 // Proceedings of VIAM. 2022. No. 10. DOI: 10.18577/2307-6046-2022-0-10-23-41. URL: https://test.viam.ru/en/journal/2022/10/3
Keywords
4, bismaleimide resins, heat-resistant polymers, fracture toughness, 4'-bismaleimidodiphenylmethane, diallyl bisphenol A, 4'-bis[2-(propenyl)phenoxy]benzophenone
Abstract

The current paper is the first part of the scientific and technical review of bismaleimide (BMI) resins chemistry. This part focuses on commercially available BMI monomers, main methods of their preparation and various compositions of BMI resins. Modifications of bismaleimides with various comonomers (diamines, aminohydrazides, allyl and propenyl compounds) are shown. Strength and performance properties of bismaleimide resins are given and their main advantages and disadvantages are determined.

Reference list
  1. Polymerizing Bismaleimides and Polyimides Therefrom: pat. US 3929713A; filed 14.08.74; publ. 30.12.75.
  2. Mukhametov R.R., Akhmadiyeva K.R., Soloveva N.A., Gulyayev A.I. Increase in water resistance of bismaleimide binder. Trudy VIAM, 2017, no. 5 (53), paper no. 08. Available at: http://www.viam-works.ru (accessed: June 14, 2022). DOI: 10.18577/2307-6046-2017-0-5-8-8.
  3. Kablov E.N., Chursova L.V., Babin A.N., Mukhametov R.R., Panina N.N. Developments of FSUE "VIAM" in the field of melt binders for polymer composite materials. Polimernye materialy i tekhnologii, 2016, vol. 2, no. 2, pp. 37–42.
  4. Kablov E.N. Innovative developments of FSUE «VIAM» SSC of RF on realization of «Strategic directions of the development of materials and technologies of their processing for the period until 2030». Aviacionnye materialy i tehnologii, 2015, no. 1 (34), pp. 3–33. DOI: 10.18577/2071-9140-2015-0-1-3-33.
  5. Valueva M.I., Zelenina I.V., Zharinov M.A., Akhmadieva K.R. World market of high temperature polyimide carbon plastic (review). Trudy VIAM, 2019, no. 12 (84), paper no. 08. Available at: http://www.viam-works.ru (accessed: April 22, 2022). DOI: 10.18577/2307-6046-2019-0-12-67-79.
  6. Dolgova E.V., Lavrova K.S. Application of cyanate ester materials (review). Part 1. Aviation and space structures. Trudy VIAM, 2021, no. 4 (98), paper no. 04. Available at: http://www.viam-works.ru (accessed: June 14, 2022). DOI: 10.18577/2307-6046-2021-0-4-48-60.
  7. 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.
  8. Kablov E.N., Erofeev V.T., Zotkina M.M., Dergunova A.V., Moiseev V.V., Rimshin V.I. Plasticized epoxy composites for manufacturing of composite reinforcement. Journal of Physics: Conference Series. «International Conference on Engineering Systems 2020», 2020, p. 012031.
  9. Evsyukov S.E., Pohlmann T., Wiel M. Modern approaches to the processing of bismaleimide resins. Current Trends in Polymer Science, 2020, vol. 20, pp. 2–14.
  10. Campbell F.C. Thermoset Resins: The Glue That Holds the Strings Together. Manufacturing Processes for Advanced Composites. Elsevier, 2004, р. 77.
  11. Chattha M.S., Dickie R.A., Carduner K.R. Epoxy-modified diallylbisphenol A and bis(maleimidopheny1)methane thermoset compositions: composition and dynamic mechanical thermal analysis. Industrial Engineering Chemistry Research, 1989, vol. 28, pp. 1438–1441.
  12. Ren Z., Cheng Y., Li Y., Xiao F. Preparation and characterization of soluble bismaleimide-triazine resinsbased on asymmetric bismaleimide. Journal of Applied Polymer Science, 2016, vol. 134, p. 44519. DOI: 10.1002/app.44519.
  13. Santhosh Kumar K.S., Reghunadhan Nair C.P., Sadhana R., Ninan K.N. Benzoxazine–bismaleimide blends: curing and thermal properties. European Polymer Journal, 2007, vol. 43, рр. 5084–5096.
  14. Wilkinson S.P., Ward T.C., McGrath J.E. Effect of thermoplastic modifier variables on toughening a bismaleimide matrix resin for high-performance composite materials. Polymer, 1993, vol. 34, pp. 870–884.
  15. Iredale R.J., Ward C., Hamerton I. Modern advances in bismaleimide resin technology: A 21st century perspective on the chemistry of addition polyimides. Progress in Polymer Science, 2017, vol. 69, pp. 1–21.
  16. Synthesis of N-Aryl-Maleimides: pat. US 2444536A; filed 14.05.46; publ. 06.07.48.
  17. Mangalgiri P.D. Polymer-matrix Composites for High-temperature Applications. Defence Science Journal, 2005, vol. 55, no. 2, pp. 175–193.
  18. Nanjan M.J., Sivaraj K. Synthesis and characterization of certain new poly(bisimide)s. I. Journal of Polymer Science. Part A: Polymer Chemistry, 1989, vol. 27, pp. 375–388.
  19. BISMALEIMIDES. Available at: https://www.hos-tec.com/products/bismaleimides/ (accessed: June 14, 2022).
  20. COMPIMIDE® bismaleimides resins. Available at: https://healthcare.evonik.com/ en/pharmaceuticals/api-contract-manufacturing/technological-capabilities/bismaleimide-resins (accessed: June 14, 2022).
  21. MATRIMID® markets & applications. Available at: https://huntsman-pimcore.equisolve-dev.com/Documents/US_2019_High_Performance_Components_Selector_Guide.pdf (accessed: June 14, 2022).
  22. Bismaleimide group – Products. Available at: https://www.daiwakasei.jp/en/products_bismaleimide.html (accessed: June 14, 2022).
  23. Cymer Commercial Monomers and Additives. Available at: https://www.cymerllc.com/organis-intermediates/ (accessed: June 14, 2022).
  24. Takeda S., Akiyama H., Kakiuchi H. Synthesis and properties of bismaleimide resins containing ether bonds. Journal of Applied Polymer Science, 1988, vol. 35, pp. 1341–1350.
  25. Evsyukov S., Klomp-de Boer R., Stenzenberger H.D., Pohlmann T., Wiel M. A new m-xylylene bismaleimide-based high performance resin for vacuum-assisted infusion and resin transfer molding. Journal of Composite Materials, 2019, vol. 53, pp. 3063–3072.
  26. Vygodsky Ya.S., Adigezalov V.A., Askadsky A.A. Synthesis and study of network polymers based on aliphatic bismaleimides and card diamines. Vysokomolekulyarnye soyedineniya, 1979, vol. (A) XXI, no. 12, pp. 2672–2678.
  27. Hu Z., Li S., Zhang C. Synthesis and characterization of novel chain-extended bismaleimides containing fluorenyl cardo structure. Journal of Applied Polymer Science, 2008, vol. 107, pp. 1288–1293.
  28. Xiong X., Chen P., Yu Q. et al. Synthesis and properties of chain-extended bismaleimide resins containing phthalide cardo structure. Polymer International, 2010, vol. 59, pp. 1665–1672.
  29. Wang C., Hwang H., Wiley J. Synthesis and properties of novel naphthalene-containing bismaleimides. Journal of Applied Polymer Science, 1996, vol. 60, pp. 857–863.
  30. Dao B., Hawthorne D.G., Hodgkin J.H. et al. Preparation and characterization of some novel bismaleimide monomers and polymers based on diaminobisimides. High Performance Polymers, 1996, vol. 8, no. 2, pp. 243–263.
  31. Stenzenberger H.D. Bismaleimide Resins. ASM handbook. Ed.: D.B. Miracle, S.L. Donaldson. 2001, vol. 21, pp. 97–104.
  32. Evsyukov S.E., Pohlmann T., Stenzenberger H.D. m-Xylylene bismaleimide: a versatile buildingblock for high-performance thermosets. Polymers for Advanced Technologies, 2015, vol. 26, pp. 574–580.
  33. Crivello J.V. Polyaspartimides: condension of aromatic diamines and bismaleimide compounds. Journal of Polymer Science: Polymer Chemistry Edition, 1973, vol. 11, pp. 1185–1200.
  34. Cross-linked Resins: pat. US 3562223; filed 08.07.68; publ. 09.02.71.
  35. Mikhailin Yu.A. Heat-resistant polymers and polymeric materials. St. Petersburg: Professiya, 2006, 624 p.
  36. Tung C.M., Lung C.L., Liar T.T. Effect of cure states on the mechanical properties of bismaleimides. Part 3: Dynamic mechanical properties and fracture energies. Polymer Materials Science Engineering, 1985, vol. 52, pp. 139–143.
  37. Stenzenberger H.D. Addition Polyimides. Advances in Polymer Science, 1994, vol. 117, pp. 165–220.
  38. Thermosetting imide resins from amino acid hydrazide: pat. US 4211861A; filed 29.11.78; publ. 08.07.80.
  39. Reyx D., Campistron I., Caillaud C. Thermal reaction between N-phenylmaleimide and 2-allylphenol as a model for the crosslinking reaction in bismaleimide polymerization with diallylbisphenol A. Macromolecular Chemistry and Physics, 1995, vol. 196, pp. 773‒785.
  40. Fischer G. High temperature and toughened bismaleimide composite materials for aeronautics. Materials. Université de Lyon, 2015, pp. 12–20.
  41. Rozenberg B.A., Dzhavadyan E.A., Morgan R., Shin E. High-performance Bismaleimide Matrices: Cure Kinetics and Mechanism. Polymers for Advanced Technologies, 2002, vol. 13, pp. 837–844.
  42. John B., Reghunadhan Nair C.P. Syntactic Foams. Handbook of Thermoset Plastics. Elsevier Ink., 2014, vol. 13, p. 520.
  43. Morgan R.G., Shin E.E., Rosenberg B., Jurek A. Characterization of the cure reactions of bismaleimide composite matrices. Polymer, 1997, vol. 38, no. 3, pp. 639–646.
  44. Enoki T., Takeda T., Ishii K., Shibahara S. Effects of catalysts on the model reactions of several maleimide resin systems‒(I) Amine-modified maleimide. High Perfomance Polymers, 1994, vol. 6, p. 385.
  45. Satheesh Chandran M., Reghunadhan Nair C.P. Maleimide-Based Alder-Enes. Handbook of Thermoset Plastics. Elsevier Ink., 2014, vol. 12, pp. 459–470.
  46. Zahir A., Renner A. Process for the Manufacture of Crosslinked Polymers which Contain Imide Groups: pat. US 4100140A; filed 18.06.76; publ. 11.07.78.
  47. Babkin A.V., Erdni-Goryaev E.M., Solopchenko A.V., Kepman A.V. Infusion bismaleimide binders for polymer composite materials. Khimiya i khimicheskaya tekhnologiya, 2015, no. 58, pp. 54–57.
  48. Stenzenberger H.D., Konig P. Comonomers for Bismaleimides: o,oʹ-Diallylbisphenols. High Perfomance Polymers, 1989, vol. 1, no. 3, pp. 239–246.
  49. Qu C., Zhao L., Wang D. et al. Bis[4-(4-maleimidephen-oxy)phenyl] propane/N,N-4,4-bismaleimidodiphenylmethyene blend modified with diallyl bisphenol A. Journal of Applied Polymer Science, 2014, vol. 131, pp. 40395 (1–8).
  50. Resines durcissables: pat. EP 0230741; filed 10.12.86; publ. 05.08.87.
  51. [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxyl]-terminated compounds: pat. WO 2017/045931; filed 02.09.16; publ. 23.03.17.
  52. Stenzenberger H.D. Recent Advances in Thermosetting-Polyimides. British Polymer Journal, 1988, vol. 20, pp. 383–396.