Document Type

Thesis

Date of Award

9-30-1987

Degree Name

Master of Science in Engineering Science- (M.S.)

Department

Chemical Engineering, Chemistry and Environmental Science

First Advisor

David S. Kristol

Second Advisor

Richard Clyde Parker

Third Advisor

Howard S. Kimmel

Abstract

The synthesis of four new monomers containing vinyl and carbamate functional groups was attempted. The desired products were N-m-methacryloxyphenyl-O-phenyl carbamate, N-p-methacryloxy-O-phenyl carbamate, m-N-phenylcarbamato-2-methacryloxyethoxy benzoate, and p-N-phenylcarbamato-2-methacryloxyethoxy benzoate. The carbamate functional group was derived by the Lewis Acid catalyzed reaction of meta-aminophenol, para-aminophenol, meta-aminobenzoic acid, and para-aminobenzoic acid with diphenyl carbonate. The vinyl function was derived, in the case of the aminophenols, by reaction with methacrylyl chloride, and in the case of the aminobenzoic acids, with 2-hydroxyethyl methacrylate.

Partial products only were prepared, these being the two carbamate functional phenols, the two carbamate functional benzoic acids, the two methacryloxy functional derivatives of the aminophenols, and the two 2-methacryloxyethoxy aminobenzoates. The products were characterized by elemental analysis and infrared spectroscopy.

It is believed that the desired products may be useful as dentin bonding agents for restorative purposes. Additionally, the reaction products of both meta- and paraaminobenzoic acid with 2-hydroxyethyl methacrylate were highly viscous, resinous fluids exhibiting properties which may prove these substances to be useful as contact- or pressure-sensitive adhesives.

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