Development of novel cardo-containing phenylethynyl-terminated polyimide with high thermal properties

Abstract

A phenylethynyl‐terminated reactive diluent [Card‐4‐phenylethynylphthalic anhydride (PEPA)], which contained fluorenyl cardo structures, was successfully synthesized and used as a modifier for flexible phenylethynyl‐terminated imide oligomer (PEI‐PEPA). The chemical structure, crosslink characterization, molecular weights, and thermal properties of the products were characterized. The imide systems with addition of 10, 20, 30, and 40 wt% Card‐PEPA to PEI‐PEPA (PEI‐PEPA‐Card) and their cured resin systems were prepared. The thermal curing behaviors of imide systems at different heating rates were analyzed by using differential scanning calorimetry. Thermal properties such as glass transition temperature (Tg) and char yield at 800°C of the resultant resin systems were studied by differential scanning calorimetry, dynamic mechanical analysis, and thermogravimetric analysis. The rheological properties were also investigated using a dynamic rheometry. These properties were found to be outstanding compared with pure PEI‐PEPA. The uncured imide systems exhibited lower Tg and lower isothermal viscosity with addition of Card‐PEPA. Furthermore, the Tg and char yield of the cured resin systems increased with addition of Card‐PEPA. The cured resin systems containing 40 wt% Card‐PEPA exhibited the highest Tg of 359°C and char yield at 800°C of 66.5%. Copyright © 2016 John Wiley & Sons, Ltd.

1,4‐Bis(2,3‐dicarboxyl‐phenoxy)benzene dianhydride‐based phenylethynyl terminated thermoset oligoimides for resin transfer molding applications

“…At last, monomers with large pendant groups (like TFDB and 1,4,4‐6FAPB) are preferred, because they can also enhance the processability of the oligomers. Besides the CF 3 , monomers with the benzene ring or other pendant groups as side groups have also been investigated for PETIs. In recent years, Yokota and coworkers first used 2‐phenyl‐4,4′‐diaminodiphenyl ether ( p ‐ODA) to prepared dissoluble Tri A‐X .…”

Phenylethynyl-terminated oligoimides with ultra-low melt viscosity derived from 1,4-bis(3,4-dicarboxy phenoxy)benzene dianhydride

“…5 Therefore, PETIs have received sustained attention over these years. [6][7][8][9][10][11] In recent years, it was found that oligomers with calculated molecular weight of 750 g mol À1 showed good features for resin transfer molding (RTM) processing. RTM is more desirable for composite fabrication than conventional autoclave techniques because of its relatively low manufacturing cost and the solvent-free feature.…”

“…On the other hand, monomers with large pendant groups are preferred, because they can also enhance the processability of the oligomers. Besides TFDB and 1,4,4-6FAPB, monomers with the benzene ring [30][31][32][33] or other pendant groups 10,34 as side groups have also been investigated for PETIs. In recent years, Miyauchi et al firstly used 2-phenyl-4,4 0 -diaminodiphenyl ether (p-ODA) to prepare dissoluble Tri A-X.…”

Highly soluble phenylethynyl‐terminated imides derived from mellophanic dianhydride (MPDA)

“…Yang et al have also developed highly soluble PETIs from 4,4′‐(9‐fluorenylidene)dianiline (BAFL) and 4,4′‐oxydiphthalic anhydride (ODPA), and the oligoimide solution in N,N ‐dimethylacetamide (DMAc) with 30 wt% of solid content was used to prepared composites . Hu et al also prepared highly soluble oligoimides by the reaction of 2,3,3′,4′‐diphenyl ether tetracarboxylic acid dianhydride ( a ‐ODPA) and 3,4′‐oxydianiline (3,4′‐ODA), and the solid content of oligoimide solutions in NMP and DMAc can reach 40 wt% . However, the boiling points of these solvents are still too high to be removed during the fabrication.…”

“…18 Hu et al also prepared highly soluble oligoimides by the reaction of 2,3,3′,4′-diphenyl ether tetracarboxylic acid dianhydride (a-ODPA) and 3,4′-oxydianiline (3,4′-ODA), and the solid content of oligoimide solutions in NMP and DMAc can reach 40 wt%. 19,20 However, the boiling points of these solvents are still too high to be removed during the fabrication. Hence, the oligoimides with high solubility in low-boiling point organic solvents in their fully imidized form are highly required.…”