Synthesis and Polymerization of a New Acrylic Monomer Containing Bicycloheptenone Moiety

Um D

Korea Polymer Journal, Vol.1, No.1, 21-26, April, 1993

A new acrylic monomer containing tetraphenyl-substituted bicycloheptenone moiety was prepared through the designed reaction scheme. The reaction intermediates obtained during the series of reaction were identified. The final product of white solid monomer (mp. 202-204 ℃, MW:593.7) was homopolymerized and copolymerized with methyl methacrylate (MMA) in N,N-dimethylformamide (DMF) by using a radical initiator, 2,2''-azobisisobutyronitrile (AIBN). The copolymer reactivity ratios of the monomer and MMA at high conversions were found to be 0.31 and 1.06, respectively, according to the calculation of Kelen-Tudos method. UV, NMR and elemental analysis were employed to determine the composition of the copolymer. The results from each method were close within an experimental error range

[References]

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[1] Fuchs B, Israel J. Chem., 3, 44 (1965)

[2] Fuchs B, Yankelevich S, Israel J. Chem., 6, 511 (1968)

[3] Fuchs B, J. Chem. Soc.(C), 68 (1968)

[4] Fuchs B, Scharf G, J. Chem. Soc.-Chem. Commun., 226 (1974)

[5] Fuchs B, Scharf G, J. Org. Chem., 46, 5395 (1981)

[6] FUchs B, Israel J. Chem., 6, 517 (1968)

[7] Fuchs B, Scharf G, J. Chem. Soc.-Chem. Commun., 244 (1975)

[8] Fuchs B, Scharf G, J. Org. Chem., 44, 604 (1979)

[9] Allen CFH, Sheps LJ, Can. J. Chem., 11, 171 (1934)

[10] Dilthey W, U.S. Patent, 2,097,854 (1937)

[11] Allen CFH, Allan JV, J. Am. Chem. Soc., 64, 1260 (1942)

[12] Allen CFH, Chem. Rev., 62, 653 (1962)

[13] Schuster DJ, Lee HFT, Padwa A, Gassman PG, J. Org. Chem., 30, 2262 (1965)

[14] Um D, Harris FW, IUPAC Polymer Symposium Preprint, Molecular Design of Functional Poymers, Seoul, Korea, June 26-28 (1989)

[15] Um D, Ph.D. Dissertation, The Univ. of Akron, May (1990)

[16] Stiteler CH, U.S. Patent, 3,265,708 (1966)

[17] Tudos F, Kelen T, Folders-Berlzsnich T, Turcsanyi B, J. Macromol. Sci.-Chem., 10(8), 1513 (1976)

[18] Kennedy JP, Kelen T, Tudos F, J. Polym. Sci. A: Polym. Chem., 13, 2277 (1975)

[19] Wall FT, J. Am. Chem. Soc., 66, 2050 (1944)

[20] Odian G, Principles of Polymerization, 2nd Ed., John Wiley & Sons, New York, Chap. 6 (1981)