Synthesis of vinyl-type functionalized polynorbornenes with cyclic pendant imide side groups by using palladium-based catalyst for low dielectric constant materials

• Published in: Reactive & functional polymers 2008-12, Vol.68 (12), p.1619-1624
• Main Authors: Liu, Binyuan, Li, Yang, Mathews, Anu Stella, Wang, Yige, Yan, Weidong, Abraham, Sinoj, Ha, Chang-Sik, Park, Dae-Won, Kim, Il
• Format: Article
• Language: English
• Subjects: Applied sciences; Catalysis; Catalysts; Conversion; Dielectric constant; Dielectric properties; Exact sciences and technology; Imides; Insulation; Microprocessors; Monomers; Organic polymers; Palladium(II) catalysts; Physicochemistry of polymers; Polarity; Polymerization; Polynorbornenes; Preparation, kinetics, thermodynamics, mechanism and catalysts; Transition metal chemistry
• ISSN: 1381-5148
• DOI: 10.1016/j.reactfunctpolym.2008.09.003

A set of functionalized polynorbornenes with various substituted pendant imide groups ( N-substituent imide group = adamantyl, cyclohexyl, tolyl, and phenyl) have been prepared via vinylic pathway by using di-μ-chloro-bis-(6-methoxybicyclo[2.2.1]-hept-2-ene- endo-5σ,2π)-palladium(II) catalyst as a means of developing materials for low dielectric constant. The effects of molar ratio of monomer to catalyst, solvent polarity, reaction time, and temperature on the polymerization of substituted norbornene-5,6-dicarboximide were investigated. Among the monomers used, exo- N-cyclohexyl-norbornene-5,6-dicarboximide recorded the highest activity, giving 90% conversion in 30 min. All the resulting functionalized polynorbornenes are characterized by good thermal properties (∼5% weight loss at 440 °C) and low dielectric constants (2.26–2.53), which are desirable for the next generation of microprocessors and memory for computers to provide insulation in the increasingly shrinking feature sizes of faster microprocessors.