Synthesis and assessment of the effect of monomer feed ratio and Lewis acids on copolymerization of butyl methacrylate/1-octene

Document Type : Original research

Authors

Department of Polymer Science, Iran Polymer and Petrochemical Institute, P. O. Box: 14965/115, Tehran, Iran

Abstract

This study was designed to investigate the effect of molar ratio of 1-octene and type as well as concentration of Lewis acids on the free radical copolymerization of butyl methacrylate (BMA) with 1-octene. The synthesized copolymers have been substantially described by FTIR, 1H NMR, GPC and DSC. The quantitative 1H NMR and GPC demonstrated that by increase in the molar ratio of 1-octene and Lewis acids to BMA, the incorporation of 1-octene in the copolymer backbone enhanced, Mn reduced and polydispersity became narrower. The maximum incorporation of 1-octene (13.7%) was observed for sample CSC7 having [1-octene/BMA] of 3 mol% and [AlCl3/BMA] of 1.5 mol%. The DSC results confirmed the NMR and GPC outcomes, suggesting a decrease in Tg by increasing 1-octene in the copolymer backbone. Moreover, it is found that temperature has a remarkable influence on the copolymerization behavior. The results also showed that by substituting the acrylate monomer from butyl methacrylate to butyl acrylate, the incorporation of 1-octene increased.

Keywords

Main Subjects

References

  1. Kebritchi A, Nekoomanesh M, Mohammadi F, Khonakdar H, Wagenknecht U (2019) Thermal behavior of ethylene/1-octene copolymer fractions at high temperatures: Effect of hexyl branch content. Polyolefins J 6:127-38
  2. Phan MT, Van Luu B, Pham LN (2021) Synthesis and elaboration of modified comb type (maleic anhydride-α-tetradecene) copolymers for cold flow improvers of biodiesel. Vietnam J Sci Technol Eng 63:13-19
  3. Fu X, Zhu L, He B, Zhu L (2020) Influence of Monomer Ratio on the Performance of Poly (octadecyl acrylate-co-styrene) as Pour-Point Depressants. Energ Fuel 34: 6791-6798
  4. Mu H, Zhou G, Hu X, Jian Z (2021) Recent advances in nickel mediated copolymerization of olefin with polar monomers. Coordin Chem Rev 435: 213802
  5. Kukrety A, Sharma B, Senthilkumar T, Gupta P, Jain SL (2021) Design, synthesis, and performance evaluation of poly (long-chain α-olefin-co-acrylates) as multifunctional additives for lubricating base oils. Polymer Bull 28:1-4
  6. Guo L, Liu W, Chen C (2017) Late transition metal catalyzed α-olefin polymerization and copolymerization with polar monomers. Mater Chem Front 1:2487-2494
  7. Li G, Xu G, Ge Y, Dai S (2020) Synthesis of fluorinated polyethylene of different topologies via insertion polymerization with semifluorinated acrylates. Polym Chem 11: 6335-6342
  8. Xiao C, Jiang L, Dan Y (2019) Effect of long-chain branch of poly (methyl acrylate-co-1- octene) on the vulcanization and mechanical properties. Ind Eng Chem Res 58: 7857-7865
  9. Venkatesh R, Harrisson S, Haddleton DM, Klumperman B (2004) Olefin copolymerization via controlled radical polymerization: copolymerization of acrylate and 1-octene. Macromolecules 37: 4406-4416
  10. Lutz JF, Kirci B, Matyjaszewski K (2003) Synthesis of well-defined alternating copolymers by controlled/living radical polymerization in the presence of Lewis acids. Macromolecules 36: 3136- 3145
  11. Wu Z, Wang Z, Wang BW, Peng CH, Fu X (2019) Visible-light-induced living/controlledradical copolymerization of 1-octene and acrylic monomers mediated by organocobalt complexes. Macromolecules 53: 212-222
  12. Kaur S, Singh G, Gupta VK (2019) Solid acid clay mediated copolymerization of methyl acrylate and 1-octene: 2D NMR substantiation of predominant alternating comonomer sequence. J Polym Sci Pol Chem 47: 2156-2162
  13. Kaur S, Singh G, Kothari AV, Gupta VK (2009) Methyl acrylate/1-octene copolymers: Lewis acid- mediated polymerization. J Appl Polym Sci 111:87-93
  14. Carlson RK, Lee RA, Assam JH, King RA, Nagel ML (2015) Free-radical copolymerisation of acrylamides, acrylates, and α-olefins. Mol Phys 113: 1809-1822
  15. Venkatesh R, Klumperman B (2004) Olefin copolymerization via controlled radical polymerization: copolymerization of methyl methacrylate and 1-octene. Macromolecules 37:1226-1233
  16. Venkatesh R, Harrisson S, Haddleton DM, Klumperman B (2004) Olefin copolymerization via controlled radical polymerization: copolymerization of acrylate and 1-octene. Macromolecules 37: 4406-4416
  17. Carlson RK, Lee RA, Assam JH, King RA, Nagel ML (2015) Free-radical copolymerisation of acrylamides, acrylates, and α-olefins. Mol Phys 113: 1809-1822
  18. Keyes A, Basbug Alhan HE, Ordonez E, Ha U, Beezer DB, Dau H, Liu YS, Tsogtgerel E, Jones GR, Harth E (2019) Olefins and vinyl polar monomers: bridging the gap for next generation materials. Angew Chem Int Edit 58: 12370- 12391
  19. Saikia M, Baruah U, Borphukan S, Saikia PJ, Saikia BK, Baruah SD (2019) Controlled copolymerization of 1-octene and butyl methacrylate via RAFT and their nonisothermal model-free thermokinetic decomposition study. J Polym Sci Pol Chem 57: 2093-2103.
  20. Zhao N, Cheng R, Dong Q, He X, Liu Z, Zhang S, Terano M, Liu B (2014) Tuning the short chain branch distribution of ethylene and 1-hexene copolymers by SiO2-supported silyl chromate catalyst with different Al-alkyl co-catalysts. Polyolefins J 1: 93-105
  21. Kaur S, Singh G, Kothari AV, Gupta VK (2009) Methyl acrylate/1-octene copolymers: Lewis acid- mediated polymerization. J Appl Polym Sci 111: 87-93
  22. Xiao C, Yu Y, Jiang L, Dan Y (2018) Insight into copolymerization of methyl (meth) acrylate and 1- octene with aluminum trichloride. Ind Eng Chem Res 57: 16604-16614
  23. Lutz JF, Kirci B, Matyjaszewski K (2003) Synthesis of well-defined alternating copolymers by controlled/living radical polymerization in the presence of Lewis acids. Macromolecules 36: 3136- 3145
  24. Luo R, Chen Y, Sen A (2008) Effect of lewis and brønsted acids on the homopolymerization of acrylates and their copolymerization with 1-alkenes. J Polym Sci Pol Chem 46: 5499-5505
  25. Jozaghkar MR, Jahani Y, Arabi H, Ziaee F (2018) Preparation and assessment of phase morphology, rheological properties, and thermal behavior of low-density polyethylene/polyhexene-1 blends. Polym-Plast Technol Eng 57: 757-765
  26. Kim HJ, Han J, Son Y (2020) Effect of a monomer composition on the mechanical properties and glass transition temperature of a waterborne polyurethane/graphene oxide and waterborne polyurethane/MWCNT nanocomposite. Polymers 12: 2013
  27. Jozaghkar MR, Ziaee F, Ardakani HR, Ashenagar S, Jalilian M (2019) Kinetics of high-temperature bulk thermal polymerization of methyl styrene. Iran J Polym Sci Technol 32: 227-240
  28. Odian G (2004) Principles of polymerization. John Wiley & Sons
  29. McCurdy KG, Laidler KJ (1964) Rates of polymerization of acrylates and methacrylates in emulsion systems. Canadian J Chem 42: 825-829

Files

Cited by

History

  • Receive Date: 15 December 2021
  • Revise Date: 17 January 2022
  • Accept Date: 01 February 2022
  • First Publish Date: 04 February 2022

Share

How to cite

Statistics