College of Science and Health Theses and Dissertations

Date of Award

Fall 11-23-2021

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Paul Vadola, PhD

Second Advisor

Quinetta Shelby, PhD

Third Advisor

Greg Kharas, PhD

Abstract

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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