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Title page for etd-0825109-151350


URN etd-0825109-151350 Statistics This thesis had been viewed 2196 times. Download 365 times.
Author Pei-Yuan Su
Author's Email Address a113010@hotmail.com
Department Chemical Engineering
Year 2008 Semester 2
Degree Master Type of Document Master's Thesis
Language Chinese&English Page Count 134
Title Studies on the synthesis of the triphenylamine monomer and properties of the thermoreversible hydrogels prepared from theirs
Keyword
  • triphenylamine
  • N-isopropylacrylamine
  • thermoreversible
  • thermoreversible
  • N-isopropylacrylamine
  • triphenylamine
  • Abstract The thesis includes two parts. In first part, 4-Amino triphenylamine (ATPA) was firstly synthesized by nucleophilic substitution of 4-fluoronitrobenzene and diphenylamine in this study, and then acylation of ATPA was carried out via acryloyl chloride to obtain 4-acrylamido triphenylamine (AATPA). Then, a series of thermosensitive hydrogels were prepared by copolymerization of AATPA and N-isopropyl acrylamide (NIPAAm) by UV irradiation. The effect of AATPA content in the copolymeric gels on the swelling ratio, mechanical properties, and drug release behaviors of the gels was investigated. Results showed that the swelling ratios of the copolymeric gels decreased from 8 (g/g) to 2 (g/g) when the hydrophobic monomer AATPA content in the copolymeric gel increased from 1 mol% to 5 mol% due to the decreasing hydrophilicity. In addition, the thermosensitive behavior obviously decreased with increasing of AATPA content in the gels, but the mechanical properties and crosslinking density of the gel swelling in the ethanol solution increased with increasing of AATPA content. The swelling ratios of hydrogels were changed by increasing AATPA content in the different solvents. In addition, the corresponding copolymers of NIPAAm/AATPA copolymeric gels, were synthesized. The UV absorption and PL emission were measured. The results showed that the maximum UV absorption wavelength and PL intensity of the copolymers and the AATPA homopolymer appeared in the invisible region.
    In second part, 4-Cyano triphenylamine was firstly synthesized by nucleophilic substitution of 4-fluorobenzonitrile and diphenylamine in this study. Then, the hydrolysis and acidification to obtain 4-cyano triphenylamine, and then further to carried out acylation via oxalyl chloride, and finally react with HEMA to obtain methacryloyloxy ethylene oxycarbonyl triphenylamine (METPA). Then, a series of thermosensitive hydrogels were prepared by copolymerization of METPA and N-isopropyl acrylamide (NIPAAm) by UV irradiation. The effects of METPA contents on the swelling ratio, mechanical properties of the gels were investigated. Results showed that when the hydrophobic monomer METPA content in the copolymeric gel increased from 1 mol% to 5 mol%, the swelling ratios of the copolymeric gels decreased from 8 (g/g) to 7 (g/g); the gel strength and crosslinking density increase 2 and 3 times, respectively, in the 95% ethanol solutions; the caffeine drug release ratio also decrease from 60% to 30%, but the indomethacin release ratio increased from 40% to 90%; the pore size diameter also increase with METPA contents. In photoluminescent behavior, the intensity of photoluminescent increased with an increase of the content of METPA in the copolymeric hydrogel. On the other hand, the copolymers with corresponding copolymeric hydrogels were prepared by the free radical polymerization. Their photoluminescent in various solvent (10-5M) were measured by UV and PL techniques. Their results showed that the maximum absorption wavelength is independent of the METPA content, but the intensity of photoluminescence is dependent on the content of METPA.
    Advisor Committee
  • Wen-Fn Lee - advisor
  • Chung-Yi Wang - co-chair
  • Shiaw-Guang Hu - co-chair
  • Files indicate in-campus access at 5 years and off-campus access at 5 years
    Date of Defense 2008-07-28 Date of Submission 2009-09-07


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