Synthesis and properties of a novel naphthyl-containing self-promoted phthalonitrile polymer

Abstract

A novel naphthyl-based self-promoted phthalonitrile monomer, 4-(8-amino-2-naphthyloxy)phthalonitrile (8-ANP), was successfully synthesized via nucleophilic substitution reaction through a one-pot reaction, and it exhibited desirable processing feature with a wide process window (temperature between the melting point and the cure temperature) and low complex viscosity. The activation energy ( Ea) value of the self-promoted curing reaction was ascertained using integral isoconversional Starink method. Even without post cure at high temperature for a long time, the properties of 8-ANP polymers were still outstanding, which exhibited high glass transition temperatures, high storage modulus, low average coefficient of thermal expansion, and excellent thermal and thermo-oxidative stabilities.

Enhanced properties of phthalonitrile resins reinforced by novel phthalonitrile-terminated polyaryl ether nitrile containing fluorene group

“…This was due to introduction of BPPEN oligomers containing longer backbone structures caused loose chain packing and resulted in lower cross-linking density. Even so, all the cured resins containing BPPEN exhibited excellent thermal stability (T d5 exceeding 520 C), which was higher than the most reported phthalonitrile resins 21,[31][32][33] (T d5 ranged from 410 C to 520 C). Specifically, C y1000 of cured pure APN was 76% and C y1000 of the cured BPAPN-5, BPAPN-10, and BPAPN-15 was 76%, 77%, and 76%, respectively.…”

An overview of high-performance phthalonitrile resins: fabrication and electronic applications

“…To solve this problem, some researchers have developed a series of phthalonitrile monomers with self-catalytic capability. 46–48 The curing reaction of the phthalonitrile monomer is a nucleophilic addition reaction, so the functional groups with active hydrogen could be introduced into the chemical structure of the phthalonitrile monomer by the molecular design for achieving the purpose of curing the resin without any additional catalysts. As an example, Zeng et al 49 synthesized a phthalonitrile monomer consisting of a hydroxyl group with self-polymerization ability that can be cured at 225 °C without adding any catalysts.…”

Preparation of phthalonitrile resins containing siloxane linkages with improved processability

“…[1][2][3][4][5][6][7][8] Concurrently, to expand the application prospects of phthalonitrile resin in the marine, aerospace, and microelectronics industries, new types containing imide, 9 bismaleimide, 10 benzoxazine, 11 novoazole, 12 alkyl, 13 amino, 14 and other functional phthalonitrile monomers have been designed and successfully prepared. However, phthalonitrile resin usually contains biphenyl, 15,16 naphthyl, 17,18 pyridyl, 19,20 and other rigid groups. The existence of these rigid groups imparts phthalonitrile with good thermal stability; however, they also result in the phthalonitrile monomer having a high melting point and processing difficulties.…”