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Synthesis of new stimuli responsive polymeric material
Author
Chen, Choon Tow
Supervisor
Roshan Deen Gulam Rasool
Teo, Yong Chua
Abstract
An aliphatic tertiary amine-group of N-substitute acrylamide, N-acryloyl-N’-octylpiperazine homo linear polymer was prepared. The project is concerned with the synthesis of cationic monomer in a stepwise manner, as well as to introduce a convertible synthetic method for the preparation an extendable range of N-N’-disubstituted piperazine derivatives. This involved four essential scale-up reaction steps, namely N-alkylation of N-Boc-piperazine, which yielded a recovery of up to 82% of N-Boc-N'-octylpiperazine, de-protection of the tert-butyloxycarbonyl (Boc) group that gave 60% of N-octylpiperazine; and direct coupling of the deboc product with acryloyl chloride. The resultant adduct, N-acryloyl-N’-octylpiperazine monomer was isolated in 60% yield and subsequent homo-polymerization was carried out. The synthesized intermediates were purified by either column chromatography over silica gel using the appropriate polarity solvents or a simple distillation. In structural elucidation, intermediate compounds and final monomer were characterized by 1H NMR and IR analyses. The structure of the cationic monomer contains both hydrophilic piperazine diamine and hydrophobic octyl terminal side chain. It is expected to display dual-responsiveness towards pH and temperature stimuli. Based on its “surfactant-like” chemical structure, the novel monomer is proposed as a suitable candidate for polymeric micellar-, nano- and core-shell materials. With different combinations of the existing monomers, it is possible to obtain entirely new and functional hybrid polymers.
Date Issued
2013
Call Number
QD381 Che
Date Submitted
2013