سنتز و شناسایی رزین 4،'4- بیس(‌مالئیمیدو)دی‌فنیل‌متان و بررسی رفتار پخت آن در آمیخته‌سازی با رزین اپوکسی

نوع مقاله : پژوهشی

نویسندگان

تهران، دانشگاه صنعتی مالک اشتر، پژوهشکده مهندسی کامپوزیت، گروه مهندسی پلیمر، صندوق پستی 1774-15875

چکیده

فرضیه‌: رزین بیس‌مالئیمید با توجه به خواص مکانیکی و گرمایی مطلوبی که دارد می‌تواند در آمیخته‌سازی با رزین اپوکسی، خواص آن را بهبود دهد. رزین‌ 4،'4-بیس‌(‌مالئیمیدو)دی‌فنیل‌متان (BMI) یکی از انواع رزین‌های بیس‌مالئیمید است که قابلیت پخت هم‌زمان با رزین اپوکسی به‌وسیله عامل‌های پخت آمینی را دارد و می‌توان با چرخه‌ پخت یکسان هر دو رزین را پخت کرد و از این راه خواص فیزیکی-مکانیکی کامپوزیت‌های بر پایه اپوکسی را بهبود داد.
روش‌ها: رزین‌ BMI با تشکیل ماده‌ حدواسط آمیک اسید از واکنش مالئیک انیدرید و متیلن دی‌آنیلین (MDA) در حلال استون، سپس آبگیری از آمیک اسید تشکیل‌شده و بستن حلقه‌ ایمیدی با استفاده از استیک انیدرید و سدیم استات و کاتالیزگر تری‌اتیل آمین سنتز شد. محصول با  طیف‌نمایی زیرقرمز تبدیل فوریه (FTIR) و رزونانس مغناطیسی هسته‌ هیدروژن (1HNMR) شناسایی شد. رزین بیس‌مالئیمید سنتزشده در مقادیر مختلف 10، 20، 30 و 40phr  با رزین اپوکسی DGEBA و عامل پخت MDA مخلوط شد و کامپوزیت تهیه‌شده از آمیخته‌ DGEBA/BMI و الیاف شیشه و عامل پخت MDA مورد آزمون استحکام برشی بین‌لایه‌ای (ILSS) قرار گرفت. در نهایت، رفتار پخت آمیخته‌ DGEBA/BMI با نسبت 30phr  از BMI و نسبت 38.294phr از عامل پخت MDA، با آزمون‌های گرماسنجی پویشی تفاضلی (DSC) دما ثابت و طیف‌نمایی FTIR بررسی شد.
یافته‌ها: رزین 4،'4-بیس‌(‌مالئیمیدو)‌دی‌فنیل‌متان برای بهبود خاصیت ILSS کامپوزیت تهیه‌شده بر پایه رزین اپوکسی DGEBA و الیاف شیشه استفاده شد. مقدار 52.50MPa به‌عنوان مقدار بهینه ILSS در دمای 78 درجه سلسیوس برای آمیخته دارای 30phrبیس‌مالئیمید به‌دست آمد. رزین‌های DGEBA و BMI به‌ترتیب قابلیت پخت 73 و %78 به‌طور هم‌زمان با عامل پخت MDA در دمای 160درجه سلسیوس  را دارند، به‌طوری که تکمیل پخت آمیخته اپوکسی و بیس‌مالئیمید به دمای بیش از  160 درجه مانند دمای 20 درجه سلسیوس نیاز دارد.

کلیدواژه‌ها

عنوان مقاله [English]

Synthesis and Characterization of 4,4'-Bis(maleimido)diphenylmethane Resin and Evaluation of Its Curing Behavior in Blending with Epoxy

نویسندگان [English]

  • Mahdi Payamani
  • Hassan Fattahi
  • Mehrzad Mortezaei
Department of Polymer Engineering, Composite Research Institute, Faculty of Materials and Manufacturing Technologies, Malek Ashtar University of Technology, Tehran, Iran
چکیده [English]

Hypothesis: Bismaleimide resin, due to its favorable mechanical and thermal properties, can improve the properties of epoxy resin. 4,4'- Bis(maleimido)diphenylmethane resin (BMI) is one of bismaleimide resins that can be cured simultaneously with epoxy resin by amine curing agents and both resins can be cured with the same curing cycle. This improves the physical-mechanical properties of epoxy-based composites.
Methods: BMI resin was synthesized using the reaction between maleic anhydride and 4,4'-diaminodiphenyl methane in acetone to form an intermediate of amic acid. The dehydration of the amic acid was carried out to form an imide using acetic anhydride, triethylamine and sodium acetate. The product was characterized by FTIR and 
1H NMR spectroscopy techniques. The synthesized resin was blended with DGEBA epoxy resins in different amounts of 10, 20, 30 and 40 phr. Next, the blends were cured by 4,4'-diaminodiphenyl methane as a curing agent, and the composites were prepared from the blends and glass fibers. The interlaminar shear strength (ILSS) of the prepared composites was measured as a key parameter of composites. The curing behavior of epoxy/bismaleimide blend was investigated using isothermal differential scanning calorimetry (DSC) and FTIR spectroscopy.
Findings: 4,4'-Bis(maleimido)diphenylmethane resin was used to improve ILSS properties of the composite prepared based on DGEBA epoxy resin and glass fibers. The value of 52.50 MPa was obtained as the optimum value of ILSS at 78°C for the mixture with 30 phr of bismaleimide. DGEBA and BMI resins have the ability to simultaneously cure by 73% and 78% using MDA curing agent at 160°C. Full curing of the epoxy and bismaleimide mixture requires a temperature higher than 160°C, such as 220°C.

کلیدواژه‌ها [English]

  • Bismaleimide
  • Epoxy
  • Blend
  • Curing
  • ILSS

مراجع

  1. Pham H.Q. and Marks M.J., Epoxy Resins, Ullmann’s Encyclopedia of Industrial Chemistry, 13, 156-244, 2000.
  2. Kulshreshtha A.K. and Vasile C., Handbook of Polymer Blends and Composites, Rapra Technology Limited, United Kingdom, 1, 2002.
  3. Payamani M., Fattahi H., and Mortezaei M., Dual-Curing Systems of Epoxy Resin for Using in Prepreg Manufacturing, Basparesh (Persian), 12, 56-67, 2022.
  4. Naderi-Samani H., Razavi R.S., Loghman-Estarki M., Ramazani M., Barekat M., Mishra A., and Fattahi H., The Effects of Cloisite 20A Content on the Adhesion Strength and Corrosion Behavior of Poly(amide-imide)/Cloisite 20A Nanocomposite Coatings, B. Eng., 175, 107154, 2019.
  5. Halpin J.P., Pandolfini P.P., Biermann P.J., Kistenmacher T.J., Hunter L.W., O’Connor J.S., and Jablonski D.G., F/A-18E/F Program Independent Analysis, Johns Hopkins APL Tech. Dig., 18, 33, 1997.
  6. Soles C.L., Chang F.T., Gidley D.W., and Yee A.F., Contributions of the Nanovoid Structure to the Kinetics of Moisture Transport in Epoxy Resins, Polym. Sci., Part B: Polym. Phys., 38, 776-791, 2000.
  7. Wang W., Perng L., Hsiue G., and Chang F., Characterization and Properties of New Silicone-Containing Epoxy Resin, Polymer, 41, 6113-6122, 2000.
  8. Jin F.L., Li X., and Park S.-J., Synthesis and Application of Epoxy Resins: A Review, Ind. Eng. Chem., 29, 1-11, 2015.
  9. Gholipour I., Amiri I., Fattahi H., and Mortezaei M., Effect of Solid Epoxy Resin on Properties of an Epoxy/Glass Prepreg, J. Polym. Sci. Technol. (Persian), 34, 485-497, 2021.
  10. Jahani M., Fatahi H., and Mortezaeei M., Effect of Aromatic Amine Structure as a Curing Agent on Molecular Packing and Mechanical Properties of Cured Epoxy Resin, J. Polym. Sci. Technol. (Persian), 32, 267-276, 2019.
  11. Akherati Sany R., Mortezaei M., and Amiri Amraei I., Improving Fracture Toughness of Epoxy Nanocomposites by Silica Nanoparticles, Iran. J. Polym. Sci. Technol. (Persian), 30, 3-17, 2017.
  12. Zamanian M., Ashenai Ghasemi F., and Mortezaei M., Interphase Characterization and Modeling of Tensile Modulus in Epoxy/Silica Nanocomposites, Appl. Polym. Sci., 138, 49755, 2021.
  13. Wu Z., Gao S., Chen L., Jiang D., Shao Q., Zhang B., Zhai Z., Wang C., Zhao M., Ma Y., Zhang X., Weng L., Zhang M., and Guo Zh., Electrically Insulated Epoxy Nanocomposites Reinforced with Synergistic Core–Shell SiO2@MWCNTs and Montmorillonite Bifillers, Chem. Phys., 218, 1700357, 2017.
  14. Chen C. and Curliss D., Processing and Morphological Development of Montmorillonite Epoxy Nanocomposites, Nanotechnology, 14, 643, 2003.
  15. Qi Z., Zhang W., He X., and Yang R., High-Efficiency Flame Retardency of Epoxy Resin Composites with Perfect T8 Caged Phosphorus Containing Polyhedral Oligomeric Silsesquioxanes (P-POSSs), Sci. Technol., 127, 8-19, 2016.
  16. Seidi F., Jouyandeh M., Taghizadeh A., Taghizadeh M., Habibzadeh S., Jin Y., Xiao H., Zarrintaj P., and Saeb M.R., Polyhedral Oligomeric Silsesquioxane/Epoxy Coatings: A Review, Innov., 9, 3-16, 2020.
  17. Zhou Y., Wu P., Cheng , Ingram J., and Jeelani S., Improvement in Electrical, Thermal and Mechanical Properties of Epoxy by Filling Carbon Nanotube, Express Polym. Lett., 2, 40-48, 2008.
  18. Kim J.A., Seong D.G., Kang T.J., and Youn J.R., Effects of Surface Modification on Rheological and Mechanical Properties of CNT/Epoxy Composites, Carbon, 44, 1898-1905, 2006.
  19. Zhang J., Kong Q., and Wang D.-Y., Simultaneously Improving the Fire Safety and Mechanical Properties of Epoxy Resin with Fe-CNTs via Large-Scale Preparation, Mater. Chem., 6, 6376-6386, 2018.
  20. Gojny F.H., Nastalczyk J., Roslaniec Z., and Schulte K., Surface Modified Multi-Walled Carbon Nanotubes in CNT/Epoxy-Composites, Phys. Lett., 370, 820-824, 2003.
  21. Sun Z., Xu L., Chen , Wang Y., Tusiime R., Cheng C., Zhou S., Liu Y., Yu M., and Zhang H., Enhancing the Mechanical and Thermal Properties of Epoxy Resin via Blending with Thermoplastic Polysulfone, Polymers, 11, 461, 2019.
  22. Kazemi M., Mortazaei M., and Amiri Amraie I., Synthesis of Benzoxazine Resin and Evaluating the Mechanical Properties of Epoxy-Benzoxazine-Silica Nanocomposites, J. Polym. Sci. Technol. (Persian), 32, 439-448, 2019.
  23. Francis B., Poel G.V., Posada F., Groeninckx G., Rao V.L., Ramaswamy R., and Thomas S., Cure Kinetics and Morphology of Blends of Epoxy Resin with Poly(ether ether ketone) Containing Pendant Tertiary Butyl Groups, Polymer, 44, 3687-3699, 2003.
  24. Wang M., Yu Y., Wu X., and Li S., Polymerization Induced Phase Separation in Poly(ether imide)-Modified Epoxy Resin Cured with Imidazole, Polymer, 45, 1253-1259, 2004.
  25. Chen J. and Taylor A.C., Epoxy Modified with Triblock Copolymers: Morphology, Mechanical Properties and Fracture Mechanisms, Mater. Sci., 47, 4546-4560, 2012.
  26. Zheng N., Sun W., Liu H.-Y., Huang Y., Gao J., and Mai Y.-W., Effects of Carboxylated Carbon Nanotubes on the Phase Separation Behaviour and Fracture-Mechanical Properties of an Epoxy/Polysulfone Blend, Sci. Technol., 159, 180-181, 2018.
  27. Dean K., Cook W.D., Zipper M., and Burchill P., Curing Behaviour of IPNs Formed from Model VERs and Epoxy Systems I Amine Cured Epoxy, Polymer, 42, 1345-1359, 2001.
  28. Karger-Kocsis J., Gryshchuk O., and Schmitt S., Vinylester/Epoxy-Based Thermosets of Interpenetrating Network Structure: An Atomic Force Microscopic Study, Mater. Sci., 38, 413-420, 2003.
  29. Iredale R.J., Ward C., and Hamerton I., Modern Advances in Bismaleimide Resin Technology: A 21st Century Perspective on the Chemistry of Addition Polyimides, Polym. Sci., 69, 1-21, 2017.
  30. Falahi A., Rajabi L., and Afshar T.F., DSC Analysis of Thermosetting Polyimides Based on Three Bismaleimide Resin Eutectic Mixtures, Polym. J., 20, 161-171, 2011.
  31. Huang F., Huang F., Zhou Y., and Du L., Preparation and Properties of Bismaleimide Resins Modified with Hydrogen Silsesquioxane and Dipropargyl Ether and Their Composites, J., 42, 261-267, 2010.
  32. Dinakaran K., Kumar R.S., and Alagar M., Bismaleimides (N, N′-Bismaleimde-4,4′-Diphenylmethane and N,N′-Bismaleimido-4,4′-Diphenylsulfone) Modified Bisphenoldicyanate–Epoxy Matrices for Engineering Applications, Manuf., 20, 299-315, 2005.
  33. Rajasekaran R., Alagar M., and Chozhan C.K., Effect of Polyethersulfone and N,N′-Bismaleimido-4, 4′-Diphenylmethane on the Mechanical and Thermal Properties of Epoxy Systems, Express Polym. Lett., 2, 339-348, 2008.
  34. Rajasekaran R. and Alagar M., Mechanical Properties of Bismaleimides Modified Polysulfone Epoxy Matrices, J. Polym. Mater. Polym. Biomater., 56, 911-927, 2007.
  35. Lin K.F. and Chen J.C., Curing, Compatibility, and Fracture Toughness for Blends of Bismaleimide and a Tetrafunctional Epoxy Resin, Eng. Sci., 36, 211-217, 1996.
  36. Kim D.S., Han M.J., and Lee J.R., Cure Behavior and Properties of an Epoxy Resin Modified with a Bismaleimide Resin, Eng. Sci., 35, 1353-1358, 1995.
  37. Dinakaran K. and Alagar M., Preparation and Characterization of Bismaleimide (N,N′-Bismaleimido-4,4′-Diphenylmethane)–Unsaturated Polyester Modified Epoxy Intercrosslinked Matrices, Appl. Polym. Sci., 85, 2853-2861, 2002.
  38. Vanaja A. and Rao R., Synthesis and Characterisation of Epoxy–Novolac/Bismaleimide Networks, Polym. J., 38, 187-193, 2002.
  39. Musto P., Martuscelli E., Ragosta G., Russo P., and Scarinzi G., An Interpenetrated System Based on a Tetrafunctional Epoxy Resin and a Thermosetting Bismaleimide: Structure–Properties Correlation, Appl. Polym. Sci., 69, 1029-1042, 1998.
  40. Sarafrazi M., Ghasemi A.R., and Hamadanian M., Optimization of Curing Conditions and Effect of Plasticizer Amount on the Mechanical and Thermal Properties of Epoxy Resin, J. Polym. Sci. Technol. (Persian), 33, 479-495, 2021.
  41. Pouladvand A.R., Mortezaei M., Fattahi H., and Amraei I.A., A Novel Custom-Tailored Epoxy Prepreg Formulation Based on Epoxy-Amine Dual-Curable Systems, A: Appl. Sci. Manuf., 132, 105852, 2020.
  42. Kumar A.A., Alagar M., and Rao R., Studies on Thermal and Morphological Behavior of Siliconized Epoxy Bismaleimide Matrices, Appl. Polym. Sci., 81, 2330-2346, 2001.
  43. Ferdosian F., Yuan Z., Anderson M., and Xu C.C., Sustainable Lignin-Based Epoxy Resins Cured with Aromatic and Aliphatic Amine Curing Agents: Curing Kinetics and Thermal Properties, Acta, 618, 48-55, 2015.
  44. Zainol I., Day R., and Heatley F., Comparison Between the Thermal and Microwave Curing of Bismaleimide Resin, Appl. Polym. Sci., 90, 2764-2774, 2003.
  45. Sithique M.A., Nagendiran S., and Alagar M., Synthesis and Characterization of Bismaleimide-Modified, Soy-Based Epoxy Matrices for Flame-Retardant Applications, High Perform. Polym., 22, 328-344, 2010.
  46. Donnellan T.M. and Roylance D., Relationships in a Bismaleimide Resin System. Part II: Thermomechanical Properties, Eng. Sci., 32, 415-420, 1992.
  47. Fasce D.P. and Williams R.J., Polycondensation of Bismaleimides with Aromatic Diamines, Bull., 34, 515-522, 1995.
  48. Hummel D., Heinen K.U., Stenzenberger H., and Siesler H., Infrared Spectroscopic Determination of the Kinetic Data of the Polymerization of Aliphatic Bismaleimides, Appl. Polym. Sci., 18, 2015-2024, 1974.

 

مجله علوم و تکنولوژی پلیمر
دوره 35، شماره 4 - شماره پیاپی 180
مهر و آبان 1401
صفحه 339-352

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