Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

Abstract

A new biobased functional norbornene was synthesized by the Diels–Alder reaction between cyclopentadiene and the fluorinated eugenol. Based on the norbornene monomer, a new polynorbornene was prepared with a high molecular weight (M n = 78 000 Da) by the standard ring opening metathesis polymerization (ROMP). This polymer displayed good film-forming ability and can be postpolymerized to form a cross-linked network at high temperature (>150 °C) via the [2 + 2] cycloaddition reaction of trifluorovinyl ether (−OCF2CF2) groups. The cross-linked polymer exhibited good transmittance (T % > 90% at 550 nm) and high thermostability with a 5% weight loss temperature of 412 °C. Moreover, no obvious glass transition temperature (T g) was observed in the DMA measurement when the temperature was elevated near the decomposition temperature of the cross-linked polymer (about 350 °C). The cured resin displayed an average dielectric constant (D k) of below 2.65 with average dissipation factor (D f) of 4.3 × 10–3 for the frequencies varying from 40 Hz to 25 MHz. The cross-linked polymer film also possessed good hydrophobicity with a contact angle of 104° (water on the surface of the film) and a surface energy of 26.8 mJ m–2. These data indicate that the combination of norbornene and the fluorinated eugenol can greatly improve properties of polynorbornene, which could have potential application in microelectronic industry. Thus, this contribution may provide a new way for the usage of the biomass.

Different Organic Peroxides that Cure Low‐k 1,2‐PB/SBS/EPDM Composites for High‐Frequency Substrate

“…This high storage modulus of the 4 pbw systems is attributed to the enhanced cross‐link density. [44] The effect of DCP and BIPB on the dynamic mechanical tests was in line with the results of the tensile tests.…”

Low Dielectric Polymers with High Thermostability Derived from Biobased Vanillin

“…The global depletion of fossil resources and the environmental issues have generated considerable interest toward the production of renewable chemicals from the biomass as the ubiquitous and renewable feedstock in recent years. − Among biomasses, lignin as the second largest quantity of renewable resource becomes an effective substitute for petrochemical-derived chemicals in aromatic polymers with excellent properties. − Starting from lignin, a functional compound named vanillin can be easily prepared. ,− Because vanillin has a naturally aromatic ring and easily modified aldehyde and hydroxyl groups, it is an ideal feedstock for the synthesis of polymers. − Therefore, studies on vanillin-based polymers, such as polyesters, polycarbonates, polyvanillin, and polyacetal, have been carried out . However, these polymers are thermoplastic, and they display low glass transition temperatures.…”

Ring-Forming Polymerization toward Perfluorocyclobutyl and Ortho-Diynylarene-Derived Materials: From Synthesis to Practical Applications

“…Over the past decades, many researchers around the world have been focused on the preparation of PFCB polymers [ 27 , 31 , 32 , 33 , 44 , 45 , 46 , 47 , 48 , 49 , 60 , 61 , 62 , 63 , 64 ]. Monomers containing TFVE moieties have been developed and used to obtain PFCB polymers [ 31 , 60 , 61 , 62 ]. PFCB precursors bearing organic-inorganic cores including siloxanes and polyhedral oligomeric silsesquioxanes (POSS) have also been reported [ 28 , 65 , 66 ].…”

“…Fang et al [ 61 ] recently reported the utility of eugenol to produce a new norbornene, TFVE-containing monomer, which can be polymerized into a crosslinked network containing PFCB moieties ( Scheme 8 ). Eugenol has become popular as a renewable bio-feedstock for the synthesis of new high-performance materials due to its ready availability at low cost and reactive hydroxyl and unsaturated functional groups [ 70 ].…”