Synthesis of fluorinated polystyrene

Volodymyr Donchak and Khrystyna Harhay
DOI: 
https://doi.org/10.23939/chcht02.01.011
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Abstract: 
Acylation of polystyrene with trifluoroacetic anhydride in a solution of aprotonic solvents, namely 1,2-dichloroethane, chlorobenzene at the presence of Lewis acid as catalyst results in obtaining of fluorinated polystyrene, which posses trifluoroacetic fragments in benzoic rings, preferably in position 4. In order to achieve a total substitution of benzene rings in polystyrene macromolecules, the ratio polystyrene : trifluoroacetic anhydride : AlCl3 must be at least 1:10:2.2 mol correspondingly
References: 

[1] Akemi H., Aoyagi T., Shinohara I., Okano T., Kataoka K., Sakurai Y.: Makromol. Chem., 1986, 187, 1627-1638.
https://doi.org/10.1002/macp.1986.021870707

[2] Kambic H.E., Murabayashi S., Nose Y.: Chem. Eng. News, 1986, 64 (15), 30-48.
https://doi.org/10.1021/cen-v064n015.p030

[3] Schmidt D.L., Coburn C.E., DeKoven B.M., Potter G.E., Meyers G.F., Fischer D.A.: Nature, 1994, 368, 39.
https://doi.org/10.1038/368039a0

[4] Pittman A.G., Wall L.A.: Fluoropolymers. Wiley-Interscience: New York 1971.

[5] Zisman W.A.: Contact Angle, Wettability, and Adhesion. Advances in Chemistry Series 43. American Chemical Society: Washington, DC 1964.

[6] Schneider J., Erdelen C., Ringsdorf H., Rabolt J.F.: Macromolecules, 1989, 22, 3475.
https://doi.org/10.1021/ma00198a045

[7] Torstensson M., Ranby B., Hult A.: Macromolecules, 1990, 23, 126.
https://doi.org/10.1021/ma00203a022

[9] Fox H.W., Zisman W. A.: J.Colloid Sci.,1950, 5, 514.
https://doi.org/10.1016/0095-8522(50)90044-4

[8] Bernett M.K., Zisman W. A.: J.Phys. Chem., 1962, 66, 1207.
https://doi.org/10.1021/j100812a518

[10] Roitman J.G., Pittman A.G.: Polym. Lett., 1972, 10, 499.
https://doi.org/10.1002/pol.1972.110100703

[11] Pittman A.G., Ludwig B.A.: J. Polym. Sci. A1, 1969, 7, 3053.
https://doi.org/10.1002/pol.1969.150071102

[12] Pittman A.G., Sharp D.L., Ludwig B.A.: J. Polym. Sci. A1, 1968, 6, 1729.
https://doi.org/10.1002/pol.1968.150060630

[13] Ramharack R., Nguyen T.H.: J. Polym. Sci. C, Polym. Lett., 1987, 25, 93.
https://doi.org/10.1002/pol.1987.140250302

[14] Yokota K., Hirabayashi T.: Polym. J., 1985, 17, 991.
https://doi.org/10.1295/polymj.17.991

[15] Lin J.W.P., Dudek L.P., Majumdar D.: J. Appl. Polym. Sci., 1987, 33, 657.
https://doi.org/10.1002/app.1987.070330227

[16] Park I.J., Lee S.B., Choi C.K. J.: J. Appl. Polym. Sci., 1994, 54, 1449.
https://doi.org/10.1002/app.1994.070541008

[17] Chapman T.M., Benrashid R., Marra K.G., Keener J.P.: Macromolecules, 1995, 28, 331.
https://doi.org/10.1021/ma00105a046

[18] Guerry-Rubio C., Viguier M., Commeyras A.: Macromol. Chem. Phy, 1995, 196 (4), 1063.
https://doi.org/10.1002/macp.1995.021960409

[19] Beyou E., Bennetau B., Dunogues J., Babin P., Teyssie D., Boileau S., Corpart J.M.: Polym. Int., 1995, 38, 237.
https://doi.org/10.1002/pi.1995.210380304

[20] B. Guyot, B. Ameduri, B.Boutevin, M. Melas, M. Viguier, A. Collet.: Macromol. Chem. Phys., 1998, 199, 1879.
https://doi.org/10.1002/(SICI)1521-3935(19980901)199:9<1879::AID-MACP1879>3.0.CO;2-D

[21] B. Ameduri, R. Bongiovanni, G. Malucelli, A.Pollicino, A. Priola: J. Polym. Sci. A, 1999, 37, 77.
https://doi.org/10.1002/(SICI)1099-0518(19990101)37:1<77::AID-POLA9>3.0.CO;2-0

[22] J.-M. Corpart, S. Girault, D. Juhue: Langmuir, 2001, 17, 7237.
https://doi.org/10.1021/la010238g

[23] A. Weissberger, E. Proskauer: Organic Solvents. Interscience Publishers, Inc. New York 1955.

[24] Miloš Hudlicky: Chemistry of organic Fluorine Compounds. 2-th edition, John Wiley & Sons 1976.

[25] Norman R., Taylor R.: Electrophilic Substitution in Benzenoid Compounds. Elsevier Publishing,

NewYork1965.

[26] Arthur C. Cope: Organic syntheses. An annual publication of satisfactory methods for the preparation of organic chemicals. New York, John Wiley and Sons 1950, 30.