College of Science and Health Theses and Dissertations

Date of Award

Fall 11-23-2021

Degree Type


Degree Name

Master of Science (MS)



First Advisor

Paul Vadola, PhD

Second Advisor

Quinetta Shelby, PhD

Third Advisor

Greg Kharas, PhD


Novel alkyl ring-substituted octyl phenylcyanoacrylates (OPCA), RPhCH=C(CN)CO2CH2(CH2)6CH3, where R is H, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-propyl, 4-i-propyl, 4-butyl, 4-t-butyl, 4-i-butyl) were prepared and copolymerized with styrene. The ethylenes were synthesized by the piperidine catalyzed Knoevenagel condensation of ring-substituted benzaldehydes and octyl cyanoacetate, and characterized by CHN analysis, IR, 1H and 13C NMR. All the ethylenes were copolymerized with styrene in solution with radical initiation (ABCN) at 70°C. The compositions of the copolymers were calculated from nitrogen analysis. Compositions of ST-OPCA copolymers ranged from 18.6 % to 27.4% of the OPCA monomer. This composition was calculated via nitrogen elemental analysis with alternating sequences of styrene. The order of relative reactivity (1/r1) with the radical end of the ST-polymer with OPCA was H (1.82) > 4-buytl (1.80) > 4-i-butyl (1.75) > 4-t-butyl (1.61) > 4-ethyl (1.46) > 3-methyl (1.44) > 4-methyl (1.31) > 4-i-propyl (1.20) > 2-methyl (1.1) and finally, 4-propyl (1.04).The copolymers were characterized by nitrogen analysis, IR, DSC and TGA. The thermal decomposition of the copolymers occurred in two steps: the first step between 200 °C to 400 °C with a slow decomposition from 400 °C to 800 °C and residue (1.8% to 6.5%).

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