Date of Award

5-1-1987

Degree Type

Dissertation

Degree Name

Ph.D.

Department

Department of Chemistry

First Advisor

Malcolm B. Polk

Abstract

The syntheses of polyesters and copolyesters containing the bicyclo[2.2.2]octane ring and spacers such as sebacoyl chloride, ethyleneglycol, 1,4-butanediol, and 1,8-octanediol are discussed. The following homopolyesters were synthesized: poly(oxy-trans-1.4- cyclohexyleneoxycarbonyl-1,4-bicyclo[2.2.2]octylenecarbonyl) I; poly[(oxy-2-bromo-l,4-phenylene)oxycarbonyl-l,4-bicyclo[2.2.2]octy-lenecarbonyl] III; and poly[oxy(2-phenyl-1,4-pheny1ene)oxycarbonyl-1.4- bicyclo[2.2.2]octylenecarbonyl] V. The following copolyesters were synthesized: poly(oxy-trans-1,4-cycl ohexyleneoxycarbonyl-l,4-bicyclo[2.2.2]octylenecarbonyl-co-oxy-trans-1,4-cyclohexyleneoxysebacoyl) II; poly[oxy(2-bromo-l,4-phenylene) oxycarbonyl-l,4-bicyclo[2.2.2]octy1enecarbonyl-co-oxy(2-bromo-l,4-phenyl ene) oxysebacoyl ] IV; poly[oxy(2-phenyl-1,4-phenyl ene)oxycarbonyl-1.4- bicyclo[2.2.2]octyl enecarbonyl-co-oxy(2-phenyl-1,4-phenylene)oxy-sebacoyl] VI; poly[oxy(2-phenyl-1,4-phenylene)oxycarbonyl-1,4-bicycl o-[2.2.2]octylenecarbonyl-co-oxyethyl eneoxycarbonyl-1,4-bicyclo[2.2.21-octyl enecarbonyl] VII; pol y[oxy(2-phenyl-1,4-phenylene)oxycarbonyl-1.4- bicyclo[2.2.2]octylenecarbonyl -co-oxybutyl eneoxycarbonyl-1,4-bicyclo[2.2.2]octylenecarbonyl] VIII; and poly[oxy(2-phenyl-l,4-phenyl ene)oxycarbonyl-1,4-bi cycl o[2.2.2]octyl enecarbonyl -co-oxyocty-1 eneoxycarbonyl-1,4-bicyclo[2.2.2]octylenecarbonyl] IX. The polyesters were characterized by IR, proton and carbon-13 NMR, DSC, TGA, solution viscosity, GPC, and polarizing optical microscopy.

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