Novel amorphous thermoplastic poly(phenylquinoxaline)s (PPQ), poly(aryl ether ketone)s (PAEKs) and poly(aryl ether phthalazine)s have been synthesized. / The reaction of an aromatic Schiff's base and a tertiary amine incorporating an activated methylene moiety in the presence of strong base to produce an enamine has been investigated. Hydrolysis of the resulting enamines resulted in deoxybenzoins which were converted to benzils by a mild oxidation reaction. This chemistry was investigated as a possible method for the synthesis of the tetraketone compounds (sometimes called bisbenzils) which serve as monomers for poly(phenylquinoxaline) polymers. Two novel monomers have been prepared, the corresponding polymers with 1,1$ sp prime$,2,2$ sp prime$-tetraminobiphenyl were synthesized and their physical properties evaluated. The novel polymers exhibited increased solvent resistance as compared to other PPQ polymers reported previously in the literature. / Two novel fluorine containing monomers were synthesized and polymerized with commercial biphenols to produce amorphous, fluorinated poly(aryl ether ketone)s. The physical properties of these polymers were evaluated and compared to those of analogous nonfluorinated polymers in order to determine what benefits can be obtained by introducing fluorine into the polymer architecture. The fluorinated polymers were found to show enhanced solubility. They were readily soluble in solvents which contain a ketone moiety, such as acetone, or cyclohexanone. / A novel dihalide monomer incorporating bulky 2-naphthalenyl moieties was synthesized and polymerized with commercial biphenols in an attempt to obtain poly(aryl ether ketone)s with extremely high glass transition temperatures (Tg's). / Several poly(aryl ether ketone) polymers were reacted with hydrazine monohydrate in the presence of a catalytic quantity of acid to produce poly(aryl ether phthalazine)s via ring closure of the o-diketone moiety in the backbone of the PAEKs. The resulting polymers are amorphous thermoplastics which displayed increased glass transition temperatures (Tg) and Young's moduli. It was found that the poly(aryl ether phthalazine)s undergo a thermal reaction above the Tg of the polymer resulting in a rearrangement of the phthalazine moiety to a quinazoline moiety. Some crosslinking of the polymers also occurs, resulting in insoluble polymers which showed an increase in the Tg.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.29018 |
| Date | January 1995 |
| Creators | Elce, Edmund |
| Contributors | Hay, Allan S. (advisor) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001472700, proquestno: NN08098, Theses scanned by UMI/ProQuest. |
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