Synthesis and Polymerization of 4-Vinylbenzylphenylsulfone

Authors

DOI:

https://doi.org/10.6000/1929-5995.2023.12.16

Keywords:

4-Vinylbenzylphenylsulfone, chloromethylstyrene, Polysulfone synthesis, free radical polymerization, copolymerization reactions

Abstract

The preparation of new sulfone monomer and polymer based on 4-Vinylbenzylphenylsulfone (4-VBPS) and free radical polymerization was investigated, based on the reaction of chloromethyl styrene with sodium phenyl sulfone (phSO2Na) in dimethylformamide (DMF), using the phase transfer catalysts 18-crown-6. Copolymerization of the prepared sulphone monomer with p-methylstyrene was carried out at 65 ˚C. Nonpolymerizable 4-Ethylbenzylphenylsulfone was also prepared. The prepared monomers and polymers were characterized by different spectroscopic techniques, the number-average molecular weights (Mn) of the resulting polymer was found to be in the range of 70,100 -73,100, with polydispersity indices (Mw/Mn) vary from 1.8 to 1.9. Photolysis of the prepared polysulfone polymer and possible grafting of methyl methacrylate (MMA) monomer will be reported.

References

Ideisan A-A. Cationic Photopolymerization by Polymeric Triphenyl Phosphonium Salts. Chemical Science International Journal 2019; 27(4): 1-7. https://doi.org/10.9734/CSJI/2019/v27i430118 DOI: https://doi.org/10.9734/CSJI/2019/v27i430118

Ideisan A-A. Synthesis and Application of Polymeric reagent P-substituted Triphenylamine). Journal of Research updated in Polymer Science 2021; 10: 51-57. https://doi.org/10.6000/1929-5995.2021.10.7 DOI: https://doi.org/10.6000/1929-5995.2021.10.7

Hagen AJM, Farral J, Frechet JM. Chemical modification of polystyrene. Polymer Bulletin 1981; 5: 111-116. https://doi.org/10.1007/BF00256143 DOI: https://doi.org/10.1007/BF00256143

Sheng Q, Stover HD. A New Route to (Chloromethyl)styrene Polymers. Macromolecules 1997; 30: 6712-6714. https://doi.org/10.1021/ma9710794 DOI: https://doi.org/10.1021/ma9710794

Sato M, Vokoyama M. Preparation of a polysulfone by polycondensation of disodium 4,4′‐oxydibenzenesulfinate with 4‐bromomethylbenzyl bromide. Macromolecular Chemistry and Physics 1984; 185: 629-634. https://doi.org/10.1002/macp.1984.021850402

Robello DR, Ulman A, Urankar EJ. Poly (p-phenylene sulfone). Macromolecules 1993; 26: 6718-6721. https://doi.org/10.1021/ma00077a004 DOI: https://doi.org/10.1021/ma00077a004

Parodi F, Polysulfones, Comprehensive Polymer Science and Supplements 1989; 561-591. https://doi.org/10.1016/B978-0-08-096701-1.00174-9 DOI: https://doi.org/10.1016/B978-0-08-096701-1.00174-9

Cansiz A, Çloşlkun M, Özdemir E. Preparation of Arylsulfone Derivative of Polystyrene with P-Toluene Sulfonyl Chloride. Journal of Macromolecular Science: Part A - Chemistry 1991; 28(Suppl 2): 143-150. https://doi.org/10.1080/00222339108054395 DOI: https://doi.org/10.1080/00222339108054395

Gould IR, Tung CH, Turro NJ, Givens RS, Matuszewski B. Mechanistic studies of the photodecomposition of arylmethyl sulfones in homogeneous. and micellar solutions. Journal of the American Chemical Society 1989; 106(6): 1789-1793. https://doi.org/10.1021/ja00318a038 DOI: https://doi.org/10.1021/ja00318a038

Iizawa T, Akatsuka S, Nishikubo T. Solid-Liquid-Solid Triphase Transfer Reaction of Poly(chloromethylstyrene). Polymer Journal 1987; 19(12): 1413-1416. https://doi.org/10.1295/polymj.19.1413 DOI: https://doi.org/10.1295/polymj.19.1413

Neckers DC, Abu-Abdoun I. p, p'-Bis ((triphenylphosphonio) methyl) benzophenone salts as photoinitiators of free radical and cationic polymerization. Macromolecules 1984; 17: 2468-2473. https://doi.org/10.1021/ma00142a003 DOI: https://doi.org/10.1021/ma00142a003

Abu-Abdoun I, Thijs l, Neckers DC. Photoinitiated polymerization of vinyl monomers by benzophenone t-butyl peresters. Journal of Polymer Science. Part A-1, Polymer Chemistry 1983; 21(11): 3129-3144. https://doi.org/10.1002/pol.1983.170211110 DOI: https://doi.org/10.1002/pol.1983.170211110

Sato M, Yokoyama M. Preparation of a polysulfone by polycondensation of disodium 4, 4′‐oxydibenzenesulfinate with 4‐bromomethylbenzyl bromide. Macromolecular Chem 1984; 185: 629-634. https://doi.org/10.1002/macp.1984.021850402 DOI: https://doi.org/10.1002/macp.1984.021850402

Givens RS, Hrinczenko B, Liu JH, Matuszewski B, Collison T. Photoextrusion of sulfur dioxide from aryl methyl sulfones: exploration of the mechanism by chemical trapping, chiral and CIDNP probes. J Am Chem Soc 1984; 106(6): 1779-1789. https://doi.org/10.1021/ja00318a037 DOI: https://doi.org/10.1021/ja00318a037

Cava MP, Schlessinger PH, Van Meter JP. The Photolytic Decomposition of Some Sulfones by an Internally Sensitized Path. J Am Chem Soc 1964; 86: 3173. https://doi.org/10.1021/ja01069a056 DOI: https://doi.org/10.1021/ja01069a056

Bamford CH, Middleton IP, Al-Lamee KG. Studies of the esterification of dextran: routes to bioactive polymers and graft copolymers. Polymer 1986; 1981-1985. https://doi.org/10.1016/0032-3861(86)90194-1 DOI: https://doi.org/10.1016/0032-3861(86)90194-1

Downloads

Published

2023-11-25

How to Cite

Abu-Abdoun, I. I. . (2023). Synthesis and Polymerization of 4-Vinylbenzylphenylsulfone. Journal of Research Updates in Polymer Science, 12, 186–191. https://doi.org/10.6000/1929-5995.2023.12.16

Issue

Section

Special Issue: Polymer Science and Metallic Composites at the Forefront: Innovations in Biomedical Polymers and Nanotechnolog