KINETIC MODELING OF THE CROSS-LINKING REACTION OF CYCLOALIPHATIC EPOXIDES WITH CARBOXYL FUNCTIONALIZED ACRYLIC RESINS - HAMMETT TREATMENT OF CYCLOALIPHATIC EPOXIDES

Cyclohexene oxide and benzoic/substituted benzoic acids were used as m odel compounds to study the reactivity of cycloaliphatic diepoxides wi th carboxyl functionalized polymers. A sigma-rho Hammett treatment of cycloaliphatic epoxides with substituted benzoic acids was used to inv estigate the reaction mechanism(s) of ester formation. The catalytic d ependence on the acid strength was obtained via a H-0 Hammett-Deyrup a cidity function. The sigma-rho Hammett treatment resulted in a positiv e rho indicating that the transi tion state or the activated complex h as a developing negative charge. This suggests that only the dissociat ed benzoic acid (or substituted benozic acids) is the attacking nucleo phile.