Preparation and properties of organo‐soluble polyimides based on 4,4′‐diamino‐3,3‐dimethyldiphenylmethane and conventional dianhydrides

4,4′‐Diamino‐3,3′‐dimethyldiphenylmethane was used to prepare polyimides in an attempt to achieve good organo‐solubility and light color. Polyimides based on this diamine and three conventional aromatic dianhydrides were prepared by solution polycondensation followed by chemical imidization. They possess good solubility in aprotonic polar organic solvents such as N‐methyl 2‐pyrrolidone, N,N‐dimethyl acetamide, and m‐cresol. Polyimide from 4,4′‐diamino‐3,3′‐dimethyldiphenylmethane and diphenylether‐3,3′,4,4′‐tetracarboxylic acid dianhydride is even soluble in common solvents such as tetrahydrofuran and chloroform. Polyimides exhibit high transmittance at wavelengths above 400 nm. The glass transition temperature of polyimide from 4,4′‐diamino‐3,3′‐dimethyldiphenylmethane and pyromellitic dianhydride is 370°C, while that from 4,4′‐diamino‐3,3′‐dimethyldiphenylmethane and diphenylether‐3,3′,4,4′‐tetracarboxylic acid dianhydride is about 260°C. The initial thermal decomposition temperatures of these polyimides are 520–540°C. © 1999 John Wiley & Sons, Inc. J Appl Polym Sci 72: 1299–1304, 1999     

Synthesis and properties of novel polyimides from 3‐(4‐aminophenylthio)‐N‐aminophthalimide

A novel, asymmetric diamine, 3‐(4‐aminophenylthio)‐N‐aminophthalimide, was prepared from 3‐chloro‐N‐aminophthalimide and 4‐aminobenzenethiol. The structure of the diamine was determined via IR and ¹H‐NMR spectroscopy and elemental analysis. A series of polyimides were synthesized from 3‐(4‐aminophenylthio)‐N‐aminophthalimide and aromatic dianhydrides by a conventional two‐step method in N,N‐dimethylacetamide and by a one‐step method in phenols. These polyimides showed good solubility in 1‐methyl‐2‐pyrrolidinone, m‐cresol, and p‐chlorophenol, except polyimide from pyromellitic dianhydride, which was only soluble in p‐chlorophenol. The 5% weight loss temperatures of these polyimides ranged from 460 to 498°C in air. Dynamic mechanical thermal analysis indicated that the glass‐transition temperatures of the polyimides were in the range 278–395°C. The tensile strengths at break, moduli, and elongations of these polyimides were 146–178 MPa, 1.95–2.58 GPa, and 9.1–13.3%, respectively. Compared with corresponding polyimides from 4,4′‐diamiodiphenyl ether, these polymers showed enhanced solubility and higher glass‐transition temperatures. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Organosoluble polyimides derived from asymmetric 2‐substituted‐and 2,2′,6‐trisubstituted‐4,4′‐oxydianilines

We report a new method for the preparation of asymmetric diamines using 4,4′‐oxydianiline (4,4′‐ODA) as the starting material. By controlling the equivalents of bromination agent, N‐bromosuccinimide, we were able to attach bromide and phenyl substituents at the 2‐ or 2,2′,6‐positions of 4,4′‐ODA. Thus, four new asymmetric aromatic diamines, 2‐bromo‐4,4′‐oxydianiline (6), 2,2′,6‐tribromo‐4,4′‐oxydianiline (7), 2‐phenyl‐4,4′‐oxydianiline (8) and 2,2′,6‐triphenyl‐4,4′‐oxydianiline (9), were synthesized by this method. Their structural asymmetry was confirmed using ¹H NMR spectroscopy. Asymmetric polyimides (PI10–PI13) were prepared from these diamines and three different dianhydrides (pyromellitic dianhydride (PMDA), 3,3′,4,4′‐biphenyltetracarboxylic dianhydride and 2,2‐bis(3,4‐dicarboxyphenyl)hexafluoropropane dianhydride) in refluxing m‐cresol. The formed polyimides, except PI10a derived from 6 and PMDA, were all soluble in m‐cresol without premature precipitation during polymerization. These polyimides with inherent viscosity of 0.41–0.96 dL g^?1, measured at a concentration of 0.5 g dL^?1 in N‐methyl‐2‐pyrrolidone at 30 °C, can form tough and flexible films. Because of the structural asymmetry, they also exhibited enhanced solubility in organic solvents. Especially, polyimides PI11a and PI13a derived from 7 and 9 with rigid PMDA were soluble in various organic solvents at room temperature. The structural asymmetry of the prepared polyimides was also evidenced from ¹H NMR spectroscopy. In the ¹H NMR spectrum of PI11a, the protons of pyromellitic moiety appeared in an area ratio of 1:2:1 at three different chemical shifts, which were assigned to head‐to‐head, head‐to‐tail and tail‐to‐tail configurations, respectively. These polyimides also exhibited good thermal stability. Their glass transition temperatures ranged from 297 to 344 °C measured using thermal mechanical analysis. © 2013 Society of Chemical Industry     

Synthesis and characterization of fluorine and nitrile containing polyimides

A series of polyimides were synthesized from new diamine, Bis [4,4′‐amino‐5,5′ trifluoromethyl phenoxy‐(hexafluoro isopropylidine) phenoxy phenyl] benzonitrile [BATFB] and various aromatic tetracarboxylic anhydrides by thermal and chemical imidization routes. The BATFB was synthesized in two steps by nucleophilic displacement reaction of 2,6‐dichloro benzonitrile, 4,4′‐(hexafluoro isopropylidine) diphenol and 2‐amino‐5‐fluoro benzotrifluoride in the presence of anhydrous potassium carbonate in N,N′‐dimethyl acetamide (DMAc) and the structure was confirmed by FTIR spectroscopy and CHNSO analyzer. The polymers were characterized by FTIR spectroscopy and thermal analysis were performed by differential scanning calorimetry and thermogravimetric analysis methods. The prepared polyimides had glass transition temperatures between 230 and 290°C and their 10% weight loss were recorded in the range 550–590°C in N₂ atmosphere. Majority of polymers are found to be soluble in most of the organic solvents such as DMSO, DMF, DMAc, m‐cresol, and THF even at room temperature and few becomes soluble on heating. The prepared polyimides showed water uptake values 0.34–0.54 wt % at room temperature. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 3455–3461, 2006     

Synthesis and properties of novel soluble and high Tg poly(ether imide)s from diamine containing 4,5‐diazafluorene and trifluoromethyl units

The synthesis and properties of soluble, high T_g and transparent aromatic polyimides containing 4,5‐diazafluorene and trifluoromethyl units in the polymer backbone on the basis of a novel diamine monomer, 9,9‐di[4‐(4‐amino‐2‐trifluoromethyl phenoxy)phenylene]‐4,5‐diazafluorene, are described. Incorporation of 4,5‐diazafluorene and trifluoromethyl groups into rigid polyimides improves their solubility and transparency without decreasing their physical properties. All of the thermal imidization polyimides are soluble at room temperature in aprotic and protic polar solvents such as N,N‐dimethylacetamide, N,N′‐dimethylformamide, dimethylsulfoxide, pyridine and m‐cresol and can be solution cast into transparent, flexible and tough films. These films have a UV–visible absorption cutoff wavelength at 386–407 nm and light transparencies of 73%–84% at a wavelength of 550 nm. In addition, the polymers exhibit high thermal stability with a glass transition temperature (T_g) of 305 to 362 °C and 5% weight loss at temperatures ranging from 525 to 543 °C in nitrogen and from 521 to 538 °C in air. The polyimide films possess tensile strengths in the range 79 ? 113 MPa, a tensile modulus of 1.75 – 2.10 GPa and elongations at break of 7% ? 16%. © 2014 Society of Chemical Industry     

Synthesis and characterization of novel polyaspartimides derived from 2,2′‐dimethyl‐4,4′‐bis(4‐maleimidophenoxy)biphenyl and various diamines

A novel bismaleimide, 2,2′‐dimethyl‐4,4′‐bis(4‐maleimidophenoxy)biphenyl, containing noncoplanar 2,2′‐dimethylbiphenylene and flexible ether units in the polymer backbone was synthesized from 2,2′‐dimethyl‐4,4′‐bis(4‐aminophenoxy)biphenyl with maleic anhydride. The bismaleimide was reacted with 11 diamines using m‐cresol as a solvent and glacial acetic acid as a catalyst to produce novel polyaspartimides. Polymers were identified by elemental analysis and infrared spectroscopy, and characterized by solubility test, X‐ray diffraction, and thermal analysis (differential scanning calorimetry and thermogravimetric analysis). The inherent viscosities of the polymers varied from 0.22 to 0.48 dL g⁻¹ in concentration of 1.0 g dL⁻¹ of N,N‐dimethylformamide. All polymers are soluble in N‐methyl‐2‐pyrrolidone, N,N‐dimethylacetamide, N,N‐dimethylformamide, dimethylsulfoxide, pyridine, m‐cresol, and tetrahydrofuran. The polymers, except PASI‐4, had moderate glass transition temperature in the range of 188°–226°C and good thermo‐oxidative stability, losing 10% mass in the range of 375°–426°C in air and 357°–415°C in nitrogen. © 1999 John Wiley & Sons, Inc. J Appl Polym Sci 73: 279–286, 1999     

Polyimides derived from 1,4‐bis [3‐oxy‐(N‐aminophthalimide)] benzene

A novel diamine, 1,4‐bis [3‐oxy‐(N‐aminophthalimide)] benzene (BOAPIB), was synthesized from 1,4‐bis [3‐oxy‐(N‐phenylphthalimide)] benzene and hydrazine. Its structure was determined via IR, ¹H NMR, and elemental analysis. A series of five‐member ring, hydrazine‐based polyimides were prepared from this diamine and various aromatic dianhydrides via one‐step polycondensation in p‐chlorophenol. The inherent viscosities of these polyimides were in the range of 0.17–0.61 dL/g. These polymers were soluble in polar aprotic solvents and phenols at room temperature. Thermogravimetric analysis (TGA) showed that the 5% weight‐loss temperatures of the polyimides were near 450°C in air and 500°C in nitrogen. Dynamic mechanical thermal analysis (DMTA) indicated that the glass‐transition temperatures (T_gs) of these polymers were in the range of 265–360°C. The wide‐angle X‐ray diffraction showed that all the polyimides were amorphous. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Synthesis and characterization of new soluble poly(ester‐imide)s containing noncoplanar 2,2′‐dimethyl‐4,4′‐biphenylene unit

A new diimide–diacid chloride (3) containing a noncoplanar 2,2′‐dimethyl‐4,4′‐biphenylene unit was synthesized by treating 2,2′‐dimethyl‐4,4′‐diamino‐biphenylene with trimellitic anhydride followed by refluxing with thionyl chloride. Various new poly(ester‐imide)s were prepared from 3 with different bisphenols by solution polycondensation in nitrobenzene using pyridine as hydrogen chloride quencher at 170°C. Inherent viscosities of the poly(ester‐imide)s were found to range between 0.31 and 0.35 dL g^?1. All of the poly(ester‐imide)s, except the one containing pendent adamantyl group 5e, exhibited excellent solubility in the following solvents: N,N‐dimethylformamide, tetrahydrofuran, tetrachloroethane, dimethyl sulfoxide, N,N‐dimethylacetamide, N‐methyl‐2‐pyrrolidinone, m‐cresol, o‐chlorophenol, and chloroform. The polymers showed glass‐transition temperatures between 166 and 226°C. The 10% weight loss temperatures of the poly(ester‐imide)s, measured by TGA, were found to be in the range between 415 and 456°C in nitrogen. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 2486–2493, 2004     

Synthesis and characterization of polyimides containing pyridine moiety

A series of new polyimides was prepared by reacting 2,6‐diaminopyridine with various aromatic dianhydrides in DMF in 1 : 1 mole ratio. All the resulting polyimides were readily soluble in organic solvents such as dimethylformamide, N,N‐dimethylacetamide, pyridine, m‐cresol, THF, etc. They also show good film‐forming ability. The polyimides exhibit good thermal stability and mechanical properties. The polymers have high T_g in the range of 252–296°C. The inherent viscosities of the polymers vary from 0.81 to 1.28 dL/g. A new class of bismaleimide and polyaspartimide as also synthesized. All the resulting polymer structures were characterized by FTIR and elemental analysis. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 1846–1853, 2004     

Synthesis and characterization of aromatic polyamides containing an s‐triazine ring with thiophenoxy linkages

A series of aromatic polyamides containing an s‐triazine ring with thiophenoxy linkages was synthesized from two new diacids, namely 2,4‐bis‐(4‐carboxyphenoxy)‐6‐thiophenoxy‐s‐triazine and 2,4‐bis‐(3‐carboxyphenoxy)‐6‐thiophenoxy‐s‐triazine, and commercially available aromatic diamines by using Yamazaki's phosphorylation reaction. The polyamides were obtained in good yields and were characterized by solubility tests, viscosity measurements, FTIR, ¹H and ¹³C NMR spectroscopy, X‐ray diffraction studies and thermogravimetric analysis. The polyamides were found to have inherent viscosities in the range of 0.35 to 0.56 dl g^?1 in N,N‐dimethylacetamide (DMAc) at 30 ± 0.1 °C. All the polyamides were readily soluble in solvents such as DMAc, N‐methyl‐2‐pyrrolidone (NMP), N,N‐dimethylformamide (DMF) and m‐cresol. Thermogravimetric analysis of the polyamides indicated no weight loss below 345 °C under a nitrogen atmosphere. Copyright © 2004 Society of Chemical Industry     

Functional copolymers of p‐cumyl phenyl methacrylate and glycidyl methacrylate: Synthesis,characterization, and reactivity ratios

Free‐radical polymerization of p‐cumyl phenyl methacrylate (CPMA) was performed in benzene using bezoyl peroxide as an initiator at 80°C. The effect of time on the molecular weight was studied. Functional copolymers of CPMA and glycidyl methacrylate (GMA) with different feed ratios were synthesized by free‐radical polymerization in methyl ethyl ketone at 70°C, and they were characterized by FTIR and ¹H‐NMR spectroscopy. The molecular weights and polydispersity indexes of the polymers and copolymers were determined by gel permeation chromatography. The copolymer composition was determined by ¹H‐NMR. The glass‐transition temperature of the polymer and the copolymers was determined by differential scanning calorimetry. The reactivity ratios of the monomers were determined by the Fineman–Ross and Kelen–Tudos methods. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 336–347, 2005     

Preparation and properties of organosoluble,colorless, and high‐pretilt‐angle polyimides based on an alicyclic dianhydride and long‐main‐chain alkyl‐group‐containing diamines

Alicyclic polyimides (PIs) were prepared from 3‐carboxylmethyl‐cyclopentane‐1,2,4‐tricarboxylic acid dianhydride and α,ω‐di(4‐aminophenoxyl)alkanes. These PIs possessed good solubility in aprotic, strongly polar solvents such as N‐methyl‐2‐pyrrolidone, N,N‐dimethylacetamide, N,N‐dimethyl formamide, and m‐cresol. They possessed high transparency in visible wavelengths and were almost colorless. The pretilt angle of a liquid‐crystal display with these PIs as the alignment layer increased linearly as the length of the alkyloxy groups increased; it was close to 5° for the PI samples PI‐10 and PI‐12. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 81: 2814–2820, 2001     

Organosoluble,low‐dielectric‐constant fluorinated polyimides based on 9,9‐bis[4‐(4‐amino‐2‐trifluoromethyl‐ phenoxy)phenyl]xanthene

A new trifluoromethylated bis(ether amine) monomer, 9,9‐bis[4‐(4‐amino‐2‐trifluoromethylphenoxy)phenyl]xanthene (BATFPX), was prepared through the nucleophilic aromatic substitution reaction of 2‐chloro‐5‐nitrobenzotrifluoride and 9,9‐bis(4‐hydroxyphenyl)xanthene in the presence of potassium carbonate, followed by catalytic reduction with hydrazine and Pd/C in ethanol. A series of novel fluorinated polyimides were synthesized from BATFPX with various commercially available aromatic tetracarboxylic dianhydrides by one‐step polycondensation in m‐cresol. The resulting polyimides were readily soluble in many organic solvents such as N,N‐dimethylacetamide and tetrahydrofuran, and afforded transparent, flexible and strong films with low moisture absorption (0.28–0.51%), low dielectric constant (2.85–3.26 at 1 MHz) and good optical transparency with UV‐visible absorption cut‐off wavelengths at 352–410 nm. All the polyimides were amorphous and exhibited high thermal stability, with glass transition temperatures of 282–330 °C, 5% weight loss temperatures above 520 °C in nitrogen or air and char yields higher than 55% at 800 °C in nitrogen. Also, these polyimides had good mechanical properties with tensile strengths of 93–118 MPa, elongations at break of 9–16% and initial moduli of 2.07–2.58 GPa. Copyright © 2011 Society of Chemical Industry     

Synthesis and characterization of Schiff‐base‐containing polyimides

Benzyl bisthiosemicarbazone and its complexes with nickel (NiLH₄) and copper (CuLH₄) were used as diamine monomers for the synthesis of new Schiff‐base polyimides. The solution polycondensation of these monomers with the aromatic dianhydrides afforded metal‐containing Schiff‐base polyimides with inherent viscosities of 0.98–1.33 dL/g (measured in N‐methyl‐2‐pyrrolidone at 25°C). The polyimides were generally soluble in a wide range of solvents such as N,N‐dimethylformamide, N,N‐dimethylacetamide, tetrahydrofuran, dimethyl sulfoxide, tetrachloroethane, hexamethylene phosphoramide, N‐methyl‐2‐pyrrolidone, ethyl acetate, and pyridine at room temperature. The initial degradation temperatures of the resultant polyimides fell in the range of 220–350°C in nitrogen with char yields ranging from 36 to 64% at 700°C. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Synthesis and characterization of polyimides from 4‐(diphenyl phosphine oxide)phenyl pyrromellitic dianhydride

A novel rigid‐rod type dianhydride monomer with phosphine oxide moiety, 4‐(diphenyl phosphine oxide)phenyl pyrromellitic dianhydride (POPPMDA), was synthesized via the Suzuki coupling reaction of 4‐(diphenyl phosphine oxide)phenyl boronic acid (POBB) and 1‐bromo‐2,3,5,6‐tetramethyl benzene (B4MB), followed by oxidation and cyclodehydration. The monomer was characterized by FTIR, NMR, EA, and melting point analyzer and utilized to synthesize polyimides with diamines such as bis(3‐aminophenyl)phenyl phosphine oxide (mDAPPO) and p‐phenylene diamine (pPDA) by varying their ratio. The polyimides were prepared via a conventional two‐step synthesis: preparation of poly(amic‐acid), followed by solution imidization. The polyimides were characterized by FTIR, NMR, DSC, TGA, and TMA, and their solubility, intrinsic viscosity, and adhesive properties were also evaluated. The polyimides exhibited high T_g (342–362°C), good thermal stability (>500°C), excellent adhesive property (134–107 g/mm), and low CTE (28–17 ppm/°C). © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Phthalonitrile‐containing poly(amide imide)s with nanoactuation properties

A series of aromatic poly(amide imide)s containing pendant phthalonitrile groups was prepared by solution polycondensation reaction of 4,4′‐diamino‐4″‐(3,4‐dicyanophenoxy)triphenylmethane, 1, or of different amounts of 1 and 1,3‐bis(4‐aminophenoxy)benzene, with a fluorinated imide diacid chloride, 2,2‐bis[N‐(4‐chloroformylphenyl)phthalimidyl]hexafluoroisopropane. The polymers were easily soluble in polar organic solvents, such as N‐methyl‐2‐pyrrolidone, N,N‐dimethylacetamide, N,N‐dimethylformamide, and dimethylsulfoxide. They can be cast from solutions into thin flexible films showing nanoactuation properties in the range of 120–450 nm, depending on the nitrile group content, when an electric voltage is applied on their surface. Electrical insulating properties of the polymer films were evaluated on the basis of dielectric permittivity and dielectric loss and their variation with the frequency and temperature. The values of the dielectric permittivity at 10 kHz and 20°C were in the range of 3.01–3.43. All polymers exhibited high thermal stability, decomposition temperature being above 420°C. POLYM. ENG. SCI., 2013. © 2012 Society of Plastics Engineers     

Synthesis and characterization of polyetherimides containing multiple ether linkages and pendent pentadecyl chains

4‐(4‐(4‐(4‐Aminophenoxy)‐2‐pentadecylphenoxy)phenoxy)aniline (APPPA) was synthesized starting from cashew nut shell liquid‐derived bisphenol, i.e. 4‐(4‐hydroxyphenoxy)‐3‐pentadecylphenol, by nucleophilic substitution reaction with 4‐chloronitrobenzene followed by reduction of the formed 4‐(4‐nitrophenoxy)‐1‐(4‐(4‐nitrophenoxy)phenoxy)‐2‐pentadecylbenzene. Three new polyetherimides containing multiple ether linkages and pendent pentadecyl chains were synthesized by one‐step high‐temperature solution polycondensation of APPPA in m‐cresol with three aromatic dianhydrides, i.e. 3,3′,4,4′‐oxydiphthalic anhydride, 4,4′‐(hexafluoroisopropylidene)diphthalic anhydride and 3,3′,4,4′‐biphenyltetracarboxylic dianhydride. Inherent viscosities and number‐average molecular weights of the polyetherimides were in the ranges 0.66–0.70 dL g^?1 and 17 100–29 700 g mol^?1 (gel permeation chromatography, polystyrene standards), respectively, indicating the formation of reasonably high molecular weight polymers. The polyetherimides were soluble in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, pyridine, m‐cresol, N,N‐dimethylformamide, N,N‐dimethylacetamide, N‐methylpyrrolidone and dimethylsulfoxide, and could be cast into transparent, flexible and tough films from their solutions in chloroform. The polyetherimides exhibited glass transition temperatures (T_g) in the range 113–131 °C. The lowering of T_g could be attributed to the combined influence of flexibilizing ether linkages and pentadecyl chains which act as ‘packing‐disruptive’ groups. The temperature at 10% weight loss (T₁₀), determined from thermogravimetric analysis in nitrogen atmosphere, was in the range 460–470 °C demonstrating good thermal stability. The virtues of solubility and large gap between T_g and T₁₀ mean that the polyetherimides containing pendent pentadecyl chains have possibilities for both solution as well as melt processability. © 2015 Society of Chemical Industry     

Synthesis and properties of fluorinated polyamideimides with high solubility

A series of fluorinated polyamideimides (PAIs) were synthesized by the direct polycondensation of a novel diimide‐diacid, 1,4‐bis(trimellitimido‐2‐trifluoromethylphenoxy) benzene (BTTFB), with aromatic diamines by using triphenyl phosphite (TPP) and pyridine as condensation agents in a medium consisting of N‐methyl‐2‐pyrrolidone (NMP) and CaCl₂. Most of the resulting polymers showed an amorphous nature. All the fluorinated PAIs were readily soluble in a variety of organic solvents such as NMP, N,N‐dimethyl acetamide, dimethylformamide, and dimethyl sulfoxide and could even be dissolved in less polar solvents such as THF and m‐cresol. The PAIs had inherent viscosities of 0.77–0.93 dL/g, depending on the diamines. All the soluble PAIs afforded transparent, flexible, and tough films that exhibited excellent thermal stability, good mechanical properties, and low moisture absorption. The glass transition temperatures of these PAIs ranged from 244 to 272°C and the 5% weight loss temperatures were >525°C in nitrogen. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 95: 321–327, 2005     

Preparation and properties of polyimides based on bis[3,5‐dimethyl‐4‐(4‐aminophenoxy)phenyl]methane

A series of polyimide (PI) thin films were synthesized based on bis[3,5‐dimethyl‐4‐(4‐aminophenoxy)phenyl]methane and conventional aromatic dianhydrides. The structures and properties of the thin films were measured with Fourier transform infrared, NMR, thermogravimetric analysis, dynamic mechanical analysis, and impedance analysis. The PI films exhibited glass‐transition temperatures in the range of 211–300°C and possessed initial thermal decomposition temperature reaching up to 457–482°C in air and 461–473°C in nitrogen. Some PI films had high solubility in organic solvents such as 1‐methyl‐2‐pyrrolidinone, N,N‐dimethylformamide, N,N‐dimethylacetamide, dimethyl sulfoxide, m‐cresol, tetrahydrofuran, and CHCl₃. The mechanical properties of these films were also examined. The dielectric constants of the films were in the range of 2.8–3.3 at 25°C. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 104: 1265–1270, 2007     

Synthesis and characterization of some aromatic polyimides

The diamine 2‐methyl‐1,3‐bis(4‐aminophenyloxy)benzene was prepared via a nucleophilic substitution reaction and was characterized with Fourier transform infrared, elemental analysis, and ¹H‐ and ¹³C‐NMR spectroscopy. The prepared diamine was also characterized with single‐crystal analysis. The geometric parameters of C₁₉H₁₈N₂O₂ were in the usual ranges. The dihedral angles between the central phenyl ring and the two terminal aromatic rings were 88.9 and 91.6°. The crystal structure was stabilized by N? H···N hydrogen bonds. The diamine was then polymerized with 3,3′,4,4′‐benzophenone tetracarboxylic acid dianhydride, 4,4′‐(hexafluoroisopropylidene)diphthalic anhydride, 3,4,9,10‐perylenetetracarboxylic acid dianhydride, and pyromellitic dianhydride by either a one‐step solution polymerization reaction or a two‐step procedure. These polymers had inherent viscosities ranging from 0.61 to 0.85 dL/gm. Some of the polymers were soluble in most common organic solvents even at room temperature, and some were soluble on heating. The degradation temperatures of the resultant polymers fell in the range of 260–500°C in nitrogen (with only 10% weight loss). The specific heat capacity at 200°C ranged from 1.0 to 2.21 J g^?1 K^?1. The temperatures at which the maximum degradation of the polymer occurred ranged from 510 to 610°C. The glass‐transition temperatures of the polyimides ranged from 182 to 191°C. The activation energy and enthalpy of the polyimides ranged from 44.44 to 73.91 kJ/mol and from 42.58 to 72.08 kJ/mol K, respectively. The moisture absorption was found in the range of 0.23–0.71%. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009