한국응용과학기술학회지 (Journal of the Korean Applied Science and Technology)

  • 제30권4호
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  • Pages.592-601
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  • 2013
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  • 1225-9098(pISSN)
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  • 2288-1069(eISSN)
한국응용과학기술학회 (The Korean Society of Applied Science and Technology)
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3-(1,8나프탈이미도)프로필메타아크릴레이트와 GMA공중합체의 합성과 물성

Synthesis of 3-(1,8-Naphthalimido) Propyl Methacrylate-GMA Copolymers and Their Physical Properties

  • 임덕점 (부경대학교 공과대학 공업화학과) ;
  • 오대희 (부경대학교 공과대학 공업화학과)
  • Lim, Deok-Jum (Dept. of Industrial Chemistry, Pukyoung National University) ;
  • Oh, Dae-Hee (Dept. of Industrial Chemistry, Pukyoung National University)
  • 투고 : 2013.11.05
  • 심사 : 2013.12.19
  • 발행 : 2013.12.30
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초록

이 연구는 3-(1,8나프탈이미도)프로필메타아크릴레이트(NIPM)와 GMA공중합체의 합성과 물성에 관한 과제로서 나프탈이미드 발색단을 가진 공중합체의 조성, 모노머 반응성비, 공명효과(Q)와 극성효과 (e), 형광특성 등을 조사하였다. Azobisisobutyronitronitryl(AIBN) 개시제와 dimethylformamide(DMF) 용매를 $60^{\circ}C$에서 공중합하였다. Fineman-Ross(F-R)와 Kelen-$T\ddot{\bar{u}}d\ddot{\tilde{o}}s$(K-T)법으로 부터 단량체 반응성비를 구하였으며, $r_1$값이 $r_2$보다 크게 나타났다. NIPM이 공중합체내에서 GMA보다 더 많음을 알 수 있다. 380 nm에서 약한 분자형광띠와 460 nm에서 강한 중합체 엑시머 형광띠가 나타났다.

This work, which was about the synthesis of 3-(1,8-Naphthalimido) propyl methacrylate and GMA copolymers and their physical properties, investigated the compositions of the copolymer, the reactivity ratios of the monomer, resonance effect(Q), polar effect(e) and fluorescence effect of 1,8-naphthalicanhydride. Azobisisobutyronitronitryl(AIBN) as an initiator was employed at $60^{\circ}C$ with dimethylformamide(DMF) of solvent for the copolymerization of NIPM. $r_1$ was found to be higher than $r_2$ from the reactivity ratios of the monomer obtained from F-R and K-T methods. NIPM was found to be more copolymerized than GMA. The fluorescence spectrums of these polymers showed a weak monomer fluorescence band at 380 nm and a strong excimer fluorescence band at about 460 nm.

키워드

참고문헌

  1. H. Shaki, K. Gharanjig. S. Rouhani. and A. Khosravi, Synthesis and photophysical properties of some novel fluorescent dyes based on naphthalimide derivatives, Journal of Photochemistry and Photobiology A: Chemistry, 216, 44 (2010). https://doi.org/10.1016/j.jphotochem.2010.09.004
  2. Jin Zhengneng, Li Najun, Wang Chuanfeng, Jiang Huajiang , Lu Jianmei and Zhou Qizhong, Synthesis and fluorescence property of some novel 1,8-naphthalimide derivatives containing a thiophene ring at the C-4 position, Dyes and pigments, 96, 204 (2013). https://doi.org/10.1016/j.dyepig.2012.07.018
  3. Ghasem R. Bardajee, Microwave-assisted solvent-free synthesis of fluorescent naphthalimide dyes, Dyes and Pigments, 99, 52 (2013). https://doi.org/10.1016/j.dyepig.2013.04.004
  4. Lai C, Garner DM, Gray JE, Brogdon BL, Peterman VC and Pieniaszek HJ. Determination of bisnafide, a novel bis-naphthalimide anticancer agent, in human plasma by high-performance liquid chromatography with UV detection. J Pharmaceut Biomed ,17, 427 (1998). https://doi.org/10.1016/S0731-7085(97)00232-X
  5. Zhang Y and Zhou C. Synthesis and activities of naphthalimide azoles as a new type of antibacterial and antifungal agents. Bioorg Med Chem Lett. 21. 4349 (2011). https://doi.org/10.1016/j.bmcl.2011.05.042
  6. Grabchev I, Moneva I, Bojinov V and Guittonneau S. Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays. J Mater Chem. 10, 1291 (2000). https://doi.org/10.1039/a909153j
  7. Veale EB. and Gunnlaugsson T. Synthesis, photophysical and DNA binding studies of fluorescent Troger's base derived 4-amino-1,8-naphthalimide supramolecularclefts. J. Org. Chem. . 75, 5513 (2010). https://doi.org/10.1021/jo1005697
  8. Ryan GJ, Quinn S and Gunnlaugsson T. Highly effective DNA photocleavage by novel "rigid" Ru(bpy)3-4-nitro-and-4-amino-1,8-naphthalimide conjugates. Inorg Chem. 47, 401 (2008). https://doi.org/10.1021/ic700967y
  9. Seung-Min OH and Dae-Hee OH, Free-Radical Copolymerization of Glycidyl Methacrylate with Phthalimidoethyl Acrylate : Synthesis and Determination of Monomer Reactivity Ratios, J. of Korean Oil Chemists. Soc., 30, 297 (2013). https://doi.org/10.12925/jkocs.2013.30.2.297
  10. Jian-Xin Yang, Xin-Liang Wang, Xue-Mei Wang and Long-He, The synthesis and spectral properties of novel 4-phenylacetylene-1, 8-naphthalimide derivatives, Dyes and Pigments, 66, 83 (2005). https://doi.org/10.1016/j.dyepig.2004.07.015
  11. TZ. Filipova, I. Grabchev and I. Petkov, Synthesis and Spectral Properties of New N-Substituted Naphthalimide Luminophores for Structral Coloration of Polymethyl methacrylate and polystyrene, J. Polym. Sci. Chem., 35, 1069 (1997). https://doi.org/10.1002/(SICI)1099-0518(19970430)35:6<1069::AID-POLA10>3.0.CO;2-4
  12. M. Fineman and S. D. Ross, Linear method for determining monomer reactivity ratios of copolymerization. J. Polym. Sci., 5, 259 (1950). https://doi.org/10.1002/pol.1950.120050210
  13. T. Kelen and F. Kelen-Tüdos, Analysis of the Linear Methods For Determing Copolymerization Reactivity Ratios. 1. A New Improved Linear Graphic Method, J. Macromol. Sci., Chem., A9, 1 (1975).
  14. T. Alfrey, Jr and C. C. Price, Reactivities in vinyl Copolymerization, J. Polym. Sci., 2. 101 (1947). https://doi.org/10.1002/pol.1947.120020112
  15. D. H. Oh, W. S. Kim and K. H. Seo, Synthesis and Spectral Properties of Poly(2-1,8-naphalimidoethylmethacrylate), Polymer Communications, 29, 108 (1988).
  16. W. S. Kim, K. H. Hong, N. K. Park, and B. K. Kwon, Synthesis and Properties of Poly(2-phthalimidoethyl methacrylate), Polymer(Korea), 13(7), 608 (1989).
  17. P. S. Vijayanand and C. S. Jone Selvamalar, A. Penlidis and S. Naniundan, Copolymers of 3,5-dimethylphenyl acrylate methyl methacrylate of monomer reactivity ratios, Polym. Int., 52, 1856 (2003). https://doi.org/10.1002/pi.1114
  18. Kelen-Tüdos and F. Turesamji J, An improved graphical method for the evaluation of molecular weight measurements on polymers, J Polym. Sci., Polym. Chem., 15, 3047 (1977). https://doi.org/10.1002/pol.1977.170151219
  19. C. S. Jone Selvamalar, T. Krithiga, A. Penlidis and S. Nanjundan, Copolymeri zation of 4-benzyloxcarbonylphenyl methacrylate with glycidylmethacrylate: synthesis, characterization, reactivity ratios and application as adhesives, Reactive Functional Polymer, 56, 89 (2003). https://doi.org/10.1016/S1381-5148(03)00028-2
  20. U. Senthilkumar, Kilivelu Ganesan and B. S. R. Reddy, Synthesis, Charact erizatio and Reactivity Ratios of Phenylethyl Acrylate/Methacrylate Copolymers, J. Polym. Research, 10, 21 (2003). https://doi.org/10.1023/A:1023938301946