화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.12, No.2, 241-247, March, 2006
Export Citation
Atom Transfer Radical Polymerization of 1,3-Butadiene Using Novel CuBr/Pyridine-2-Carboxamide Catalysts
Seoung Uk Heo, Gwang Hoon Rhee1, Dong Heon Lee2, Jung Hee Kim3, Dai Seung Choi4, and Do Weon Lee†
  • Department of Chemical Engineering, University of Seoul, Seoul 130-743, Korea
  • 1Department of Mechanical & Information Engineering, University of Seoul, Seoul 130-743, Korea
  • 2Division of Science & Technology, Chonbuk National University, Chonbuk 561-756, Korea
  • 3Department of Chemistry, Sunmoon University, Chungnam 336-708, Korea
  • 4Kumho Petrochemical R&D Center, Daejon 305-600, Korea
E-mail:
Atom transfer radical polymerization (ATRP) is one of the most successful methods to polymerize syrenes, (meth)acrylater, and a variety of other monomers in a controlled fashion. Novel ligands, 4-alkylpyridine-2-carboxamides [R=methy] (4a),t-butyl (4b), H(4c)], have been prepared through the reaction of 4- alkyl-2-cyanopyridine with water in the presence of 0.4 mol% of base in ethanol solution. The livig free radical polymerization of 1,3-butadiene was facile in the presence of the CuBr/4a catalytic system. Several effects, such as those of the ligand, solvent, and temperature, and a kinetic study of the ATRP of 1,3-butadiene(BD), were studied systematically. The optimum conditions for the ATRP of BD were [CuBr]/[4a]/[PEBr]/[BD] = 1:2:1:100 at 80℃ in veratrole solution (w/w = 1:2); these conditions yielded well-defined polybutadiene (PBD) with a narrow molecular weight distribution (1.40).
Keywords:atom transfer radical polymerization (ATRP);controlled/"living" radical polymerization;pyridine-2-carboxamide;catalyst;1,3-butadiene (BD)
  1. Matyjaszewski K, Controlled Radical Polymerization, ACS Symposium Series 685, American Chemical Society, Washington, DC (1998)
  2. Matyjaszewski K, Controlled/Living Radical Polymerization: Progress in ATRP, NMP, and RAFT, ACS Symposium Series 768, American Chemical Society, Washington, DC (2000)
  3. Matyjaszewski K, Davis TP, Handbook of Radical Polymerization, Wiley-Interscience, Hoboken (2002)
  4. Patten TE, Xia JH, Abernathy T, Matyjaszewski K, Science, 272(5263), 866 (1996)
  5. Shim SE, Shin Y, Lee H, Jung H, Chang YH, Choe S, J. Ind. Eng. Chem., 9(6), 619 (2003)
  6. Thangadurai TD, Ihm SK, J. Ind. Eng. Chem., 9(5), 563 (2003)
  7. Thangadurai TD, Ihm SK, J. Ind. Eng. Chem., 9(5), 569 (2003)
  8. Kato M, Kamigaito M, Sawamoto M, Higashimura T, Macromolecules, 28(5), 1721 (1995)
  9. Wang JS, Matyjaszewski K, J. Am. Chem. Soc., 117(20), 5614 (1995)
  10. Lee DW, Seo EY, Cho SI, Yi CS, J. Polym. Sci. A: Polym. Chem., 42(11), 2747 (2004)
  11. Lee DW, J. Ind. Eng. Chem., 10(4), 592 (2004)
  12. Heo SU, Lee DW, J. Ind. Eng. Chem., 11(6), 911 (2005)
  13. Keller RN, Wycoff HD, Inorg. Synth., 2, 1 (1946) 
  14. Matyjaszewski K, Patten TE, Xia JH, J. Am. Chem. Soc., 119(4), 674 (1997)
  15. Gordon AJ, Ford RA, Chemist's Companion, pp.445-447, John Wiley & Sons, New York (1972)
  16. Schaefer FC, Peters GA, J. Org. Chem., 26, 412 (1961)
  17. Robert TS, Paul LO, Jonathan WP, Paul DG, J. Org. Chem., 55, 2 (1990)
  18. Wade LG, Organic Chemistry, 5th Edn., pp. 971-972, John Wiley & Sons, New York (2004)
  19. Xia J, Zhang X, Matyjaszewski K, ASC Symposium Series 760, p. 207, American Chemical Society, Washington, DC (2000)
  20. Stevens MP, Polymer Chemistry: An Introduction, Oxford University Press, Oxford (1999)
  21. Patten TE, Matyjaszewski K, Adv. Mater., 10, 901 (1998)
  22. Matyjaszewski K, Davis K, Patten T, Wei M, Tetrahedron, 53, 15321 (1997)
  23. Wang XS, Luo N, Ying SK, Polymer, 40(14), 4157 (1999)
  24. Wang XS, Armes SP, Macromolecules, 33(18), 6640 (2000)
  25. Pascual S, Coutin B, Tardi M, Polton K, Vairon JP, Macromolecules, 32(5), 1432 (1999)
  26. Matyjaszewski K, Macromol. Symp., 134, 105 (1998)