Complex-Radical Copolymerization of Vinylcyclohexyl Ketones with Maleic Anhydride and N-p-tolylmaleimide
DOI:
https://doi.org/10.18321/ectj343Abstract
Some features of the formation and photochemical reactions of cyclohexylketone containing macromolecules including copolymers of vinylcyclohexyl ketone (VCHK) and its derivatives (V-a-Cl-CHK and V- d-C1-CHK) with maleic anhydride (MA) and N-p-tolylmaleimide (TMI) have been revealed. It has been established that keto-enol tautomerism is the only reaction realized in the vinylcyclohexylketone molecules having mobile hydrogen atom at a -position in the cyclohexane ring, enol form of which is formed by charge-transfer complexes with anhydride or imide of maleic acid as acceptor monomers. The kinetic parameters of these reactions, including complex-formation and copolymerization constants, as well as the ratios of chain growth rates for the participation of monomeric charge-transfer complexes and free monomers,В are all determined. It is shown that an alternative copolymerization is realized with the monomer systems containing VCHK and V- d -C1-CHK, which are carried out through a complex-mechanism due to the keto-enol tautomerism; while random copolymer enriched with vinyl ketone units is formed with the system containing oc-substituted VCHK. It is found that characteristics of photochemical reactions ofВ alternating copolymer synthesized depend on the type of substitutation in the vinyl ketone molecule; unlink VCHK-MA(TMI) and V-d-C1-CHK-MA(TMI) copolymers case which easily crosslink upon UVirradiation, and the N-substituted derivatives of these copolymers which decompose under similar condition.
References
(2). B. Capon, C. Zucco, J. Amer. Chem. Soc. 104, 7567 (1982). <a href="https://doi.org/10.1021/ja00390a030">Crossref</a>
(3). A. K. Caderstov, V.M. Novak, J. Amer. Chem. Soc. 116, 4073 (1994). <a href="https://doi.org/10.1021/ja00088a051">Crossref</a>
(4). S. Masuda, K. Minagawa, Prog. Polym. Sci. 21, 557 (1996). <a href="https://doi.org/10.1016/0079-6700(95)00025-9">Crossref</a>
(5). Z.M. Rzaev, Prog. Polym. Sci. 23, (1998), in press.
(6). S. Masuda, K. Minagawa, M. Tanaka, Y.Asahi, J. Macromol. Sci., Pure Appl. Chem. A29, 821 (1992). <a href="https://doi.org/10.1080/10601329208054119">Crossref</a>
(7). S. Masuda, M. Tanaka, T. Ota, Makromol. Chem. 187, 1087 (1986). <a href="https://doi.org/10.1002/macp.1986.021870505">Crossref</a>
(8). N.Sh. Rasulov, Z.M. Rzaev, V.P. Zuhov, Polym. Sci. USSR A25, 1723 (1983). <a href="https://doi.org/10.1016/0032-3950(83)90286-1">Crossref</a>
(9). Z.M. Rzaev, N. Sh. Rasulov, L. V. Medyakova, IN. Yu. Lezgiyev, E. Yu. Kuliyeva, V. P. Zubov, Polym. Sci. USSR A29, 540 (1987). <a href="https://doi.org/10.1016/0032-3950(87)90259-0">Crossref</a>
(10). A.Y. Kretov, N.Y. Kulchinskaya, Zh. Org. Khim.(in Russian.) 26, 208 (1956).
(11). M.W. Hanna, A.L. Ashbaugh, J. Phys. Chem. 68, 811 (1964). <a href="https://doi.org/10.1021/j100786a018">Crossref</a>
(12). T. Kelen,. F. Tud6s,./. Macromol. Sci.-Chem. A9, 1 (1975).
(13). J.A. Seiner, M. Lilt, Macromolecules 4, 308 (1971). <a href="https://doi.org/10.1021/ma60021a009">Crossref</a>
(14). L. Strzeleski. Bull. Soc. Chim. France 8, 2659 (1967).
(15). Z.M., Rzaev, L.V. Medyakova, G. Kibarer, G. Akovali, Macromolecules 27,6292(1994). <a href="https://doi.org/10.1021/ma00100a010">Crossref</a>
(16). S.G. Mamedova, A. S. Mamedov, L. V. Medyakova, Z.M. Rzaev, Polymer Science, A33, 1945 (1991). <a href="https://doi.org/10.1016/0032-3950(91)90092-5">Crossref</a>
(17). Z.M. Rzaev, G. Akovali, L. V. Medyakova, Polymer, 35, 5349 (1994). <a href="https://doi.org/10.1016/0032-3861(94)90489-8">Crossref</a>
(18). Y.S. Bokov "Foto-, Electron i Rentgenoresisty", Radio i svyaz, Moscow, 1982 (in Russian).
(19). J. Guillet, "Polymer Photophysics and Photochemistry", Cambridge University Press, Cambridge, 1985.
(20). K. Sugita, M. Ueno, Prog. Polym. Sci., 17, 319 (1992). <a href="https://doi.org/10.1016/0079-6700(92)90019-u">Crossref</a>
(21). Z.C. Tan, R.C, Daly, US Patent 4568734 (1986);Chem. Ahstr, 105, 85695a (1986).
(22). Z.C. Tan, R.C. Daly, S.S. Georgia, Proc. SPIEInt. Soc. Opt. Eng. 1984, 469; Chem. Ahstr., 101, 120860t (1984).
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