High optical transparency, low dielectric constant, and light color of organosoluble polyamides based on 10,10-bis[4-(4- amino-3-trifluoromethylphenoxy)phenyl]- 9(10H)-anthrone

Abstract

A new aromatic diamine, 10,10-bis[4-(4-amino-3-trifluoromethylphenoxy)phenyl]-9( 10H)-anthrone (BATFPA), has been synthesized from anthrone via three-step procedure. Low-temperature polycondensation of BATFPA with various aromatic dicarboxylic acid chlorides produced novel fluorinated polyamides with moderate to high inherent viscosities of 0.75–1.03 dL/g while the weight-average molecular weight and number-average molecular weight were in the range of 66,000–74,000 and 37,000–41,000, respectively. Nearly, all the polymers were readily soluble in polar solvents, such as N,N-dimethyl acetamide (DMAc), N-methyl-2-pyrrolidinone, pyridine, and tetrahydrofuran, and afforded transparent, light-colored, and flexible films upon casting from DMAc solvent. These polymers had glass transition temperatures of 249–309°C, 10% weight loss temperatures of 486–517°C, and char yields of 53–61% at 800°C under nitrogen. All polymers were amorphous and their films exhibited tensile strengths of 64–86 MPa, tensile moduli of 1.8–2.2 GPa, and elongation at break of 10–18%. These polymers had dielectric constants ranging from 3.25 to 3.76 (100 Hz), low moisture uptake in the range of 0.72–1.18%, and high transparency with an ultraviolet–visible absorption cutoff wavelength in the 360–378 nm range.

Synthesis and characterization of new cardo poly(ether amide)s containing 9(10H)-anthrone units

“…As shown in Figure 7, in contrast, the thermal and tensile properties of the resulting PAs are comparable to those of the analogous cardo PAs having a 1,4-phenylene unit and fluorine ( 6 ), 11 phthalide ( 7 ), 14 and xanthene ( 8 ) 20 groups, respectively. Besides, the T g value of the prepared PA- 5a is relatively lower than that of the reported polymer 7 , but its elongation at break is much higher than that of the polymer 7 , which may be due to the higher polarity of the side phenolphthalein group than that of pendant 9(10 H )-anthrone group.…”

“…However, there is few literature on the characteristic of introducing both bulky pendant 9(10H)anthrone group and aryl-ether linkage into the backbone of PAs. 20 Recently, we reported the synthesis of soluble, aromatic PAs bearing xanthene units. [21][22][23] Because of the incorporation of bulky xanthene units along the polymer main chain, all the polymers were amorphous, showed good solubility and good film-forming capability, and exhibited high thermal stability.…”

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

“…Among them, incorporation of fluoroalkyl groups, especially 4-trifluoromethyl, has been demonstrated to afford polyamides with desirable solubility, thermal stability, dielectric, and optical properties. [21][22][23][24][25] On the other hand, it has been reported that the polyamides containing pyridine heterocyclic units in the main chain possess excellent thermal stability and mechanical property at elevated temperature because of the symmetry and aromaticity of the pyridine ring, as well as good solubility in organic solvents owing to the polarizability resulted from the nitrogen atom in pyridine. [26][27][28][29][30] Recently, we have described the synthesis of a series of soluble fluorinated polyamides containing 4-trifluoromethylphenyl-2,6-diphenylpyridyl moiety in the macromolecule main, showing acceptable thermal properties with high glass transition temperatures up to 320°C, good optical properties and low dielectric constants.…”

New fluorinated poly(pyridine amide)s derived from 2,6-bis(4-iodophenyl)-4-(4-trifluoromethylphenyl)pyridine by C–N coupling reaction

“…[8][9][10][11] Fabrication of most polyamides, However, is extremely difficult because of their high melting or softening temperatures and their limited solubility in organic solvents. So, numerous attempts have been centered on improving their processability and solubility through the introduction of flexible linkages, [12][13][14][15][16] asymmetry or noncoplanar units [17][18][19][20] and bulky substituents such as acetoxybenzamido, 21 triphenyl, 22 4-methoxy-2-pentadecylphenylcarbamoyl, 23 trifluoroacetamido 24 and trifluoromethyl [25][26][27][28][29] into the rigid polymer backbones. On the other hand, it has been demonstrated that the polyamides containing pyridine heterocyclic units in the main chain possess excellent thermal stability and mechanical property at elevated temperature due to the symmetry and aromaticity of the pyridine ring, as well as the polarization of nitrogen atom in pyridine.…”