New soluble, transparent and heat-resistant poly(ether amide)s based on 10,10-bis[4-(4-aminophenoxy)-3-methylphenyl]-9(10H)-anthrone

Abstract

<jats:p> 10,10-Bis[4-(4-aminophenoxy)-3-methylphenyl]-9(10 H)-anthrone, as a new aromatic diamine, was synthesized from 9(10 H)-anthrone by three-step procedure. Low-temperature polycondensation of this diamine with various aromatic dicarboxylic acid dichlorides produced a series of new cardo poly(ether amide)s with moderate to high inherent viscosities of 0.86–1.43 dL g<jats:sup>−1</jats:sup> while the weight-average and number-average molecular weights were in the range of 48,600–59,800 and 29,800–35,600 g mol<jats:sup>−1</jats:sup>, respectively. All the polymers were readily soluble in polar solvents such as N, N-dimethylacetamide (DMAc), N, N-dimethylformamide, N-methyl-2-pyrrolidinone, dimethyl sulfoxide, and pyridine, and afforded transparent, flexible, and strong films upon casting from DMAc solvent. These polymers had glass transition temperatures of 254–297°C, 10% weight loss temperatures of 493–505°C, and char yields of 61–64% at 800°C in nitrogen. All polymers were amorphous and their films exhibited tensile strength of 80.7–101.4 MPa, elongation at break of 8.0–12.8%, and tensile modulus of 1.9–2.6 GPa. These polymers had low moisture uptake in the range of 2.13–4.02% and high transparency with an ultraviolet–visible absorption cutoff wavelength in the 322–375 nm range. </jats:p>

Synthesis and characterization of new aromatic copoly(ether amide)s bearing 4-trifluoromethylphenyl-2,6-diphenylpyridyl moieties in the main chain

“…To overcome these limitations, a lot of efforts have been made to prepare soluble or thermoplastic polyamides without obviously lowering the high thermal and mechanical properties. Some approaches such as introducing flexible linkages, [3][4][5] bulky pendent groups, [6][7][8][9] cardo units, [10][11][12][13][14] heterocycles rings, [15][16][17] asymmetry or noncoplanar structures [18][19][20] into the polymer backbone are valuable in improving the solubility. Among them, incorporation of fluoroalkyl groups, especially 4-trifluoromethyl, has been demonstrated to afford polyamides with desirable solubility, thermal stability, dielectric, and optical properties.…”

Polyamidation of new diamine monomers containing bulky pendant groups based on imidazole ring and fabrication of polyamide/modified‐SiO2composite: Properties and applications

“…PAs containing bulky pendant groups are of particular interest and act as packing‐disruptive segments. Voluminous groups hinder the packing of polymer chains and cause easy infiltration of solvent molecules between polymer chains; consequently, the solubility can be dramatically increased 18,23 …”