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

  • 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.

ABS 수지의 내열성 강화를 위한 화합물인 N-phenylmaleimide (PMI)는 원료로서 노란색을 띤다. 그러므로 PMI로 개질된 공중합체는 색을 나타내는데, 이에 따른 사용의 제한이 있다. 이러한 단점을 극복하기 위해 PMI의 대체재로, 원료로서 색을 띠지 않고 PMI와 비슷한 성능을 가진 N-cyclohexylmaleimide (CHMI)의 수요 또한 증가하고 있다. 그러나 CHMI는 합성 중에 여러 반응 부산물이 생성되어 정제 과정이 필수적이며, 수율도 낮아 공업화에 어려움이 있다. 본 연구에서는 이러한 문제점을 개선하고 CHMI를 공업적으로 생산하기 위해 복합 촉매를 개발하였다. 최종적으로 CHMI를 85% 수율과 99.5% 이상의 순도로 합성하였다.

Keywords

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).