DOI QR코드

DOI QR Code

Development of the Commercialization of N-Cyclohexylmaleimide for Strengthening the Whiteness and Heat Resistance of Polymer Resins

고분자 수지의 백색도 및 내열성을 향상시키는 N-Cyclohexylmaleimide의 상업화를 위한 개발

  • Ju, Sung Han (Department of Applied Chemistry, Kookmin University) ;
  • Yang, Dong Hyeon (Department of Applied Chemistry, Kookmin University) ;
  • Kim, Seok Chan (Department of Applied Chemistry, Kookmin University)
  • 주성한 (국민대학교 응용화학과) ;
  • 양동현 (국민대학교 응용화학과) ;
  • 김석찬 (국민대학교 응용화학과)
  • Received : 2020.01.29
  • Accepted : 2020.03.25
  • Published : 2020.04.10

Abstract

N-phenylmaleimide (PMI), a compound for strengthening the heat resistance of ABS resin, is a yellow crystal. Therefore, copolymers modified with PMI exhibit color, which limits their use. In order to overcome such disadvantage, the demand for N-cyclohexylmaleimide (CHMI), which has similar properties to PMI and also is a white crystal, is increasing. However, CHMI is difficult to industrialize due to the formation of various by-products during synthesis, which requires an additional purification process resulting in a low yield. In this study, composite catalysts were developed to improve these problems and industrially produce CHMI. Finally, CHMI was synthesized with a 85% yield and at least 99.5% purity.

Acknowledgement

Supported by : 국민대학교

References

  1. (a) D. Dong, S. Tasaka, S. Aikawa, S. Kamiya, N. Inagaki, and Y. Inoue, Thermal degradation of acrylonitrile-butadiene-styrene terpolymer in bean oil, Polym. Degrad. Stab., 73, 319-326 (2001) https://doi.org/10.1016/S0141-3910(01)00093-3
  2. (b) H. Ma, L. Tong, Z. Xu, Z. Fang, Y. Jin, and F. Lu, A novel intumescent flame retardant: Synthesis and application in ABS copolymer, Polym. Degrad. Stab., 92, 720-726 (2007). https://doi.org/10.1016/j.polymdegradstab.2006.12.009
  3. M. Yuksel, T. Cakir Canak, and I. E. Serhatli, Synthesis of liquid crystalline moiety containing N-cyclohexylmaleimide copolymers, Polym. Adv. Technol., 20, 312-318 (2009). https://doi.org/10.1002/pat.1269
  4. (a) K-D. Song and H-M. Li, Free radical copolymerization of N-cyclohexylmaleimide with cyclohexene, J. Macromol. Sci. A, 42, 741-750 (2005) https://doi.org/10.1081/MA-200058642
  5. (b) G. Kuhne and A. Neumaier, Copolymers of vinyl chloride with N-substituted maleimides, US patent 3756991 (1973).
  6. Korea Kumho Petrochemical CO LTD. Meeting.
  7. Global 1-Phenyl-1H-pyrrole-2,5-dione Industry 2014 Market Research Report (QYR Chemical & Material Research Center).
  8. (a) J. E. Kim, S. I. Kim, and H. J. Kwark, Method for preparing N-substituted maleimides, US Patent 20110124882 (2011)
  9. (b) Z. Yuan, B. Liao, and Y. Jie, Synthetic method of N-phenylmaleimide, CN patent 103664732 (2014)
  10. (c) B.-H. Moon and C.-S. Ju, Development of a synthetic process for N-cyclohexylmaleiamic acid isobutyl ester, Korean Chem. Eng. Res., 51(5) 545-549 (2013). https://doi.org/10.9713/kcer.2013.51.5.545
  11. (a) B.-H. Moon and C.-S. Ju, Synthetic of N-cyclohexylmaleimide and preparation of its purified particles, Korean Chem. Eng. Res., 52(1) 40-44 (2014) https://doi.org/10.9713/kcer.2014.52.1.40
  12. (b) S. I. Kim, H. J. Kwark, and J. U. U. Kim, Method for preparation of the N-substitution maleimide, Korean Patent 0923536 (2013).
  13. (a) J. E. Kim, S. I. Kim, and H. J. Kwark, Method for preparing N-substituted maleimides, US Patent 20110124882 (2011)
  14. (b) Z. Yuan, B. Liao, and Y. Jie, Synthetic method of N-phenylmaleimide, CN patent 103664732 (2014).
  15. (a) Y. Kita, M. Nakagawa, H. Kanei, and A. Fukui, Method for production of maleimides, EP Patent 0334497 (1989)
  16. (b) D. Shi, Q. Zhang, X. Xu, J. Li, and X. Cheng, Method for synthesizing N-benzyl maleimide from immobilized supported acid catalyst, CN patent 101875626 (2009).