Synthesis and properties of novel organosoluble aromatic poly(ether ketone)s containing pendant methyl groups and sulfone linkages

Abstract

Several novel aromatic poly(ether ketone)s containing pendant methyl groups and sulfone linkages with inherent viscosities of 0.62-0.65 dL/g were prepared from 2-methyldiphenylether and 3-methyldiphenylether with 4,4 0 -bis(4-chloroformylphenoxy)diphenylsulfone and 4,4 0 -bis (3-chloroformylphenoxy)diphenylsulfone by electrophilic Friedel-Crafts acylation in the presence of N,N-dimethylformamide with anhydrous AlCl 3 as a catalyst in 1,2-dichloroethane. These polymers, having weight-average molecular weights in the range of 57,000-71,000, were all amorphous and showed high glass-transition temperatures ranging from 160.5 to 1678C, excellent thermal stability at temperatures over 4508C in air or nitrogen, high char yields of 52-57% in nitrogen, and good solubility in CHCl 3 and polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone at room temperature. All the polymers formed transparent, strong, and flexible films, with tensile strengths of 84.6-90.4 MPa, Young's moduli of 2.33-2.71 GPa, and elongations at break of 26.1-27.4%.

Synthesis and characterization of novel soluble cardo poly(arylene ether ketone)s containing xanthene structures

“…Therefore, many efforts have been directed toward synthesizing soluble PEKs without scarification of their desired properties. Several approaches have been investigated to improve their solubility such as the alteration the order and ratio of ether–ketone linkage5 as well as the ratio of meta and para phenyl substitution,6 the insertion of –CR 2 7, 8 and sulfone groups,9–11 the introduction of pendant groups,12–17 and the incorporation of a noncoplanar structure18–20 in the backbone of the polymeric chain. The introduction of pendant loops along the polymer backbone has been shown to impart greater solubility, enhanced rigidity, as well as better mechanical and thermal properties.…”

Advances in the application of named reactions in polymer synthesis

“…12 Friedel-Crafts acylation has been used in polymer synthesis due to its facile preparation of wholly aromatic polyketones. [13][14][15] Recently Yuki Nagao et al 16 used commercial products as building blocks and low-cost FeCl 3 as a Catalyst, and a porous organic polymer(POP) with good porosity, excellent stability and remarkable water capture ability was designed and synthesized by Friedel-Crafts acylation reaction (Figure 2). This polymer exhibited high water absorption with abundant triazine units and sulfonic acid groups.…”

Poly(arylene ether ketone)s with low dielectric constants derived from polyhedral oligomeric silsesquioxane and difluorinated aromatic ketones

“…Recently, low‐dielectric‐constant nanocomposites have attracted a great deal of attention for microelectronics, due to their potential application in integrated circuits, which can greatly lower the resistance–capacitance (RC) time delay, cross talks, and power dissipation by reducing the capacitance between the interconnection conductor lines in the new generation of submicrometer electronics and nanometer‐sized electronics . The dielectric constant, dielectric loss, moisture uptake, and solubility are all important issues for novel intermetallic phase dielectrics .…”