Synthesis and properties of polyimides containing tetraphenylnaphthalene units

Abstract

Aromatic polyimides (PI1x) with a tetraphenylnaphthalene unit between ether linkages were synthesized from 1,4-bis[4-(aminophenoxy)phenyl]-2,3-diphenylnaphthalene (1) and various tetracarboxylic dianhydrides by a conventional two-step procedure that included ring-opening polymerization in N-methyl-2-pyrrolidone and subsequent thermal cyclic dehydration. PI1x were characterized by X-ray diffraction, differential scanning calorimetry, thermogravimetry, and dynamic mechanical analysis. PI1x had glass transition temperatures in the range of 270–315°C and all PI1x were amorphous. The structure–property relationships of these PIs were examined and compared with those of polyimides (PI2x) from 4,4′-bis(4-aminophenoxy)biphenyl (2) and polyimides (PI3x) from 1,4-bis(4-aminophenyl)-2,3-diphenylnaphthalene (3). Water absorption and dielectric constants ( ε) of the PIs were also compared and discussed on the basis of imide content per repeating unit.

Synthesis and Properties of Polyimides from Bis[4-(Aminophenoxy)phenyl] Ether and Aromatic Dianhydrides Having Various Numbers of Phenylene Units

“…3). The T g values for PI-3e-PMDA and PI-3e-0, PI-3e-1, PI-3e-2, PI-3e-3 and PI-3e-4 were 280 °C, 230 °C, 230 °C, 210 °C, 220 °C, and 210 °C, respectively (Table 1), which were slightly higher than those for PI-5e-PMDA and PI-5e-m (m = 0-4) [13], and the T g values were not dependent on m. The value for PI-3e-PMDA was the highest due to intermolecular charge transfer [19], similar to the case for previously reported polyimides from dianhydrides having various numbers of phenylene units [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”

“…We previously synthesized dianhydrides DA-m having various numbers (m) of phenylene units, DA-2 [1], DA-3 [2] and DA-4 [3]. These were used to prepare aromatic polyimides containing pquarterphenyl [1], p-quinquephenyl [2] and psexiphenyl [3] with various aromatic diamines [4][5][6][7][8][9][10][11][12][13]. The properties were compared with those of polyimides from DA-0 and DA-1, and discussed on the basis of the number (m) of phenylene units [14][15][16].…”

Preparation and Properties of Rigid Polyimides from Dianhydrides Having Various Number of Phenylene Units and <i>p</i>-Phenylenediamine

“…2). The T g values did not depend on m, and the decrement of storage modulus at the T g was smaller with increasing m, similar to the polyimides from diamines having connecting groups [1][2][3][4][5][6][7][8][9][10][11][12][13]. The decrements were smaller than those of the polyimides from diamines having connecting groups with equivalent m. 0, 1, 2, 3).…”

“…These were used to prepare aromatic polyimides containing p-quarterphenyl [1], p-quinquephenyl [2], and p-sexiphenyl [3] with commercially available aromatic diamines, such as 4,4'-oxydianiline, 3,4'-oxydianiline, 4,4'-diaminodiphenyl methane, p-phenylenediamine, and 4,4'-bis(4-aminophenoxy) biphenyl, and diamines which authors had synthesized [4][5][6][7][8][9][10][11]. The properties were compared with those of polyimides from 3,3', 4,4'-biphenyltetracarboxylic dyanhydride (DA-0) and 3,3'', 4,4''-p-terphenyltetracarboxylic dyanhydride (DA-1), and discussed on the basis of the number (m) of phenylene units [1][2][3][4][5][6][7][8][9][10][11][12][13]. The T g values depended on the connecting group and the structure of the diamine moiety, but did not depend on m, whereas there was a smaller decrease in the modulus above T g with increasing m. It is reported that the rotational barrier of the connecting group played a determining role in the value of T g [14,15].…”

“…The polyimides from p-phenylenediamine, which did not have a connecting group, had the highest T g . In this study, the properties of the polyimides PI-PP-m (m = 0, 1, 2, 3, 4) [1][2][3][4][5][6][7][8][9][10][11][12][13] prepared from p-phenylenediamine and DA-m (m = 0, 1, 2, 3, 4) were compared in detail and examined on the basis of the number (m) of phenylene unit. p-Phenylenediamine did not have a connecting group, and DA-2, DA-3, and DA-4 had more phenylene units than DA-0.…”