Thesis Title

Copolymerization of a P-Vinylbenzyl-Ended Poly(Oxyethylene) With Vinyl Monomers and Some Reactions of Poly(Oxyethylene) Derivatives

Date of Graduation

Fall 2002

Degree

Master of Science in Chemistry

Department

Chemistery

Committee Chair

Reza Herati

Subject Categories

Chemistry

Abstract

Controlled free radical polymerization has gained in importance in recent years because it enables one to synthesize polymers with controlled molecular weight, narrow molecular weight distribution, and well defined architectures. In this work we have studied controlled copolymerizations of 4-[methoxypoly(ethylene oxide)]-methylenestrene (mPEG-MS) with monomers such as styrene, p-vinylbenzyl chloride, and 4-(4-vinylbenzyloxy) benzaldehyde using 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) and dibenzoyl peroxide as the initiating system. The copolymers made in this work have been characterized by NMR, IR, and gel permeation chromatography (GPC). It is shown that the molecular weights of the copolymers increase with reaction times. The polydispersities for copolymers of mPEG-MS/styrene are in the range: 1.13-1.19, for mPEG-MS/p-vinylbenzyl chloride: 1.49, and for mPEG-MS/4-(4-vinylbenzyloxy) benzaldehyde are in the range: 1.23-1.43. The various copolymers of mPEG-MS/4-(4-vinylbenzyloxy) benzaldehyde have been modified using 2-methoxyethylamine to obtain the corresponding imine polymers. Modification of mPEG-MS/p-vinylbenzyl chloride to the corresponding amino polymer was not successful. Homopolymerization of mPEG-MS under a variety of conditions resulted in incomplete polymerization of the macromonomer. In addition, the reactions of mPEG-maleic anhydride {prepared from the reaction of 5-[methoxypoly(oxyethylene)]-(3E)-1,3 pentadiene and maleic anhydride} with amines such as 2-methylaniline, 2-(2-aminoethoxy) ethanol, and ethyl ester derivative of DL-Pheylalanine have also been studied and the hydrolyses of the amide products in buffer solutions (pHs = 5.0 and 7.4) have been investigated.

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© Tippakorn Jungsriyawongse

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