Preparation and properties of novel low dielectric constant benzoxazole‐based polybenzoxazine

Abstract

A novel benzoxazine monomer containing a benzoxazole group was synthesized using a nonsolvent method and then named DAROH‐a. The structure of DAROH‐a was confirmed by FTIR, 1H NMR, elemental analysis, and mass spectrometry. The curing reaction activation energy was calculated at 140 kJ/mol. Its corresponding crosslinked polybenzoxazines, poly(DAROH‐a), displayed a higher glass transition temperature at 402 °C, a 9% weight loss at the said temperature, and a high char yield of 42 wt % (800 °C, in nitrogen). Moreover, the dielectric constants of poly(DAROH‐a) were low and changed only slightly at different temperatures. Furthermore, the dielectric constants and dielectric loss of poly(DAROH‐a) at the same frequency barely changed from room temperature to 150 °C. The photophysical properties of poly(DAROH‐a) film were also investigated. Poly(DAROH‐a) showed an absorption peak at 280 nm. The photoluminescent emission spectrum of poly(DAROH‐a) film displayed predominant emission peaks at 521 nm. It might have potential application as high‐performance materials because of its excellent dielectric constants stability and thermal stability under high temperature. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

Hydrogen-bonding characteristics and unique ring-opening polymerization behavior ofOrtho-methylol functional benzoxazine

“…Additionally, benzoxazine monomers can be easily synthesized from various phenols, amines, and formaldehyde. This versatile synthetic method has allowed development of various benzoxazines having functional groups such as amide, imide, allyl, nitrile, furyl, and benzoxazole, which were effectively used for various chemical modifications of the benzoxazine monomers and the corresponding polybenzoxazines including cross‐linking reactions.…”

Synthesis of high thermal stability polybenzoxazoles via ortho‐imide‐functional benzoxazine monomers

“…Benzoxazine can be synthesized by Mannich condensation from phenol, amine, and formaldehyde . The major advantages of polybenzoxazine include good mechanical and thermal properties, low water absorption, high carbon residue, and low surface energy . The most interesting and unique characteristic of this class of polymers is their extraordinarily rich molecular design flexibility that allows designing a variety of molecular structures to tailor the desired properties.…”

Smart Synthesis of High-Performance Thermosets Based on ortho-Amide–Imide Functional Benzoxazines

“…The major advantages of polybenzoxazine include excellent mechanical and thermal properties, low water absorption, high char yield, and low surface free energy (Ishida and Allen, 1996;Ishida and Low, 1997;Kim et al, 1999a,b;Wang et al, 2006;Velez-Herrera and Ishida, 2009;Yagci et al, 2009;Zhang et al, 2012Zhang et al, , 2013. The most interesting and unique characteristics of this class of polymers is their extraordinarily rich molecular design flexibility that allows designing a variety of molecular structures to tailor the desired properties.…”