Title

Controlled radical polymerization mediated by novel 2-alkoxy-1,1,3,3-tetraethylisoindolines

Date of Publication

2000

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry

Subject Categories

Chemistry

College

College of Science

Department/Unit

Chemistry

Thesis Adviser

Clovia Isabel Zayas Holdsworth

Defense Panel Chair

Eric Camilo R. Punzalan

Defense Panel Member

Gerardo C. Janairo
Jaime Raul O. Janairo
Glenn V. Alea
Alumanda dela Rosa

Abstract/Summary

Novel 1,1,3,3-tetraethylisoindolin-2-yloxyl (TEISO) - based alkoxyamines which are expected to act as efficient polymerization initiators/mediators were prepared in this study. The 1,1,3,3-Tetraethylisoindolin-2-yloxylmethane (Me-TEISO), phenyl-(1,1,3,3-tetraethylisoindolin-2-yloxyl)methane (Bn-TEISO), 1-(1,1,3,3-tetraethylisoindolin-2-yloxy) terahydrofuran (THF-TEISO), 1-phenyl-(1,1,3,3-tetraethylisoindolin-2-yloxy)ethane(PE-TEISO) and 2- phenyl-2-(1,1,3,3-tetraethylisoindolin-2 -yloxy)propane, (Cu-TEISO) were successfully synthesized by coupling the radical methyl, Me-, (prepared via Fenton's reaction) and 1-phenethyl, PE- cumyl, Cu-, benzyl, Bn- and tetrahydrofuranyl, THF-(prepared via H-abstraction with diterbutylperoxyoxalate, DTBP) with TEISO.The thermal stability of these novel TEISO-based alkoxyamines were investigated. Bn-TEISO, PE-TEISO, and Cu-TEISO showed detectable dissociation at 40 - 125 degrees Celsius temperature range. Their half-lives and activation energies showed that steric crowding of the pendant R of the alkoxyamines increase the rate of dissociation and follows the trend Bn-PE-Cu-.Polymerization of styrene mediated by Cu-TEISO showed living properties only at high temperature, i.e. 110 degrees Celsius. Polymerization of MMA in the presence of Cu-TEISO showed significant termination which could be due to H-abstraction and transfer.

Abstract Format

html

Language

English

Format

Print

Accession Number

TG02979

Shelf Location

Archives, The Learning Commons, 12F Henry Sy Sr. Hall

Physical Description

114 leaves

Keywords

Polymerization; Chromatographic analysis; Spectrum analysis

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