Oligomeric aliphatic–aromatic ether containing phthalonitrile resins

Abstract

A versatile synthetic method has been developed for oligomeric aliphatic–aromatic ether containing phthalonitrile (PN) resins and applied to the preparation of three unique resin systems. The oligomeric PN monomers were prepared from the reaction of an excess amount of bisphenol A with a dihalo‐aliphatic containing compound in the presence of K2CO3 in dimethylsulfoxide, followed by end‐capping with 4‐nitrophthalonitrile in a two‐step, one‐pot reaction. These PN resin systems exhibited excellent viscosities for molding various shaped articles after thermal curing to yield crosslinked polymers. These polymers offered more mechanical flexibility, when compared with an all aromatic backbone, while still maintaining good thermal stability, dielectric properties, and low water absorption. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2186–2191

Improved Synthesis of Oligomeric Sulfone‐Based Phthalonitriles

“…The D k values for samples of 6 cured to 415 °C were measured from 1 MHz to 1.8 GHz and found to be 2.8 with the D f found to be in the range of 0.01. These values are similar to those of other resins currently being used in the fabrication of radomes and other electrical components and are also typical for PN polymers . Additionally, samples of thermosets 6 were soaked in distilled water at 25 °C for 1 month, dried, and weighed.…”

“…These values are similar to those of other resins currently being used in the fabrication of radomes and other electrical components and are also typical for PN polymers. [ 29,30 ] Additionally, samples of thermosets 6 were soaked in distilled water at 25 °C for 1 month, dried, and weighed. The maximum amount of water absorption for polymer 6 over that time was around 0.8% by weight.…”

Synthesis and Properties of A Low Melting Point Phthalonitrile Resin Containing High Density Nitrile Groups

“…The result shows that the crosslinking degree of polymers increases with the increase of curing temperature and curing time, which makes the mechanical properties of Polymer 2 more excellent. The mechanical properties of the MDTP polymers are better than those of many similar phthalonitrile resins . Because of the high nitrile contents of the MDTP monomer, the crosslinking degree of polymer can be increased.…”

“…Because of the high melting point and poor processability of the first generation of phthalonitrile monomers, flexible aromatic ether segments were introduced into the molecular structure of the monomers by Keller at Naval Laboratory (NRL) . At present, aliphatic aromatic ether, poly(ether imide), poly‐(arylene ether ketone), poly‐(arylene ether) and poly‐(arylene ether nitrile) have been reported. These monomers are usually prepared by the reaction of activated dihalogenated aromatic hydrocarbons and appropriate proportions of bisphenols to form phenolic intermediates, and then end‐capped with 4‐nitrophthalonitrile.…”

Phthalonitrile Blends: Simple Way to Improve Physical Properties by Increasing Crosslinking Density

“…and 4-nitrophthalonitrile and exhibit high melting points (195-230 °C). The second-generation PN resins are composed of oligomeric aromatic ether linkages between the terminal phthalonitrile units and are prepared through a two-step, one-pot nucleophilic displacement reaction involving activated [1,2,7,8,16] or unactivated [6,17,18] dihaloaromatic compounds and an appropriate bisphenol, followed by endcapping with 4-nitrophthalonitrile. The first-generation systems further purification.…”