A novel high-temperature naphthyl-based phthalonitrile polymer: synthesis and properties

Abstract

A novel naphthyl-based phthalonitrile monomer, 1,6-bis(3,4-dicyanophenoxy) naphthalene (1,6-BDCN), was prepared, and the phthalonitrile resin was cured with 4,4 0 -diaminodiphenyl ether (ODA) via two steps, namely, preparation of prepolymer and postcuring prepolymer at elevated temperatures. The 1,6-BDCN polymer might form triazine and phthalocyanine rings as demonstrated by FTIR spectra. The prepolymer shows fine solubility in organic solvents. The 1,6-BDCN polymer exhibits excellent structural integrity and superior thermal stability as indicated by thermogravimetric analysis (TGA). Dynamic mechanical analysis (DMA) revealed that the phthalonitrile resin has a high storage modulus and glass transition temperature (T g ). The water uptake is about 3% by weight after submersion in boiling water for 50 hours. The influence of curing processes on thermal stability and flame retardancy was also explored.

Systematic study on highly efficient Thermal Synergistic Polymerization effect between alicyclic imide moiety and phthalonitrile: Scope, Properties and Mechanism

“…As shown in Fig. 5(a), the cured polymers 55-ppc, 37-ppc, and M37-ppc showed a maximum boiling water amount of approximately 2.4%, 1.9% and 2.7%, respectively, after 60 h immersion, which is lower than that of other phthalonitrile-based polymers (about 3.0%) [32]. The sample 55-ppc was more susceptible than 37-ppc to water penetration under the same conditions due to voids or air gaps observed in SEM which is probably caused by the volatilization of unreacted CC.…”

Self-promoted phthalimide-containing phthalonitrile resins with sluggish curing process and excellent thermal stability

“…The PIPN polymer exhibited excellent thermal property with 68.6% weight retention approximately at 800 C in nitrogen atmosphere, and it showed the weight residual of 99% (T 1% ), 95% (T 5% ), 90% (T 10% ) at 476.3 C, 517.7 C and 542.6 C respectively. 16 The decomposition peaks of PIPN monomer at 436 C in nitrogen and air might be ascribe to the evaporation of the PIPN monomer, because the decomposition temperatures of PIPN polymers is much higher than 436 C ( Fig. 8) and Table 1, and it showed the T 1% , T 5% and T 10% at 481.0 C, 518.6 C and 539.6 C respectively.…”

Mechanistic and kinetic aspects of the curing of phthalonitrile monomers in the presence of propargyl groups

“…Solution NMR spectra were recorded using a Bruker Avance FTNMR spectrophotometer operating at 300 MHz. Tetra methyl silane (TMS) was used as the internal standard and acetone-d 6 and CDCl 3 were used as the solvent. 13 C crosspolarization magic angle spinning (CP-MAS) experiments were carried out using a Bruker Avance 400 MHz wide cavity solid-state NMR spectrometer operating at a resonance frequency of 100.6…”

“…Phthalonitrile polymers offer many attractive features including outstanding thermo-oxidative stability, excellent mechanical properties, low water absorptivity and superior flame resistance [1][2][3][4][5][6][7].…”