Preparation and characterization of thermostable chiral extended polyamides bearing N‐phthaloyl‐L‐leucine pendent architectures in green media

Ionic liquids (ILs) are often well‐known benign solvents capable of replacing conventional organic solvents, and they have become attractive solvents for many chemical reactions. Aromatic polyamides (PAs) have received particular interest in past years because of their high thermal and chemical resistance and their potential as high‐performance materials for different applications. In this investigation, the preparation of extended PAs derived from 5‐aminoisophthalic acid containing chiral pendent linkage (N‐phthaloyl‐L ‐leucine) with various aromatic diamines was studied. The bulky monomer 5‐(4‐methyl‐2‐phthalimidylpentanoylamino)isophthalic acid was prepared in three steps. Direct polyamidation of this monomer with several commercially available diamines in the presence of IL (1,3‐dipropylimidazolium bromide) and triphenyl phosphite gave novel PAs in good yields and inherent viscosities in the range of 0.38–0.55 dL g^?1. Because of the existence of amino acid in this architect, the resulting polymers are optically active. All of these PAs showed good solubility and readily dissolved in many organic solvents. Characterization of all the products was performed by FTIR, specific rotation, and representative ones by ¹H NMR, elemental analysis, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). TGA exhibited that two elite polymers were stable, with 10% weight loss recorded above 410 and 430°C in the nitrogen atmosphere. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Preparation and characterization of poly (ether ether ketone)s containing benzimidazolone units

A series of novel poly(ether ether ketone)s containing benzimidazolone groups (PNBEEKs) with precise structures in high yields were synthesized from various stoichiometric ratio mixtures of benzimidazolone, 4,4′-dihydroxybenzophenone and 4,4′-difluorobnzophenone via a C–N/C–O coupling reaction process using sulfolane as a solvent. The reaction was carried out at 210 °C in the presence of anhydrous potassium carbonate. The structures of the resulted polymers were characterized by means of FT-IR, ¹H NMR spectroscopy, ¹³C NMR spectroscopy, and elemental analysis, and the results were largely consistent with the proposed structure. XRD studies revealed that the incorporation of benzimidazolone groups increased the crystallinity of the resulted polymers. At the same time, as the benzimidazolone unit content in the copolymer increased, the solvent resistance properties and thermal properties of the prepared polymers improved. The polymers showed high glass transition temperatures (T_g?=?126–221 °C) and high thermal stability (T_d5%?=?497–593 °C in nitrogen, 466–588 °C in air). Moreover, the resulted polymers showed good fluorescence properties and the fluorescence emission peak was 435 nm.     

Soluble new optically active polyamides derived from 5‐(4‐methyl‐2‐phthalimidylpentanoylamino)isophthalic acid and different diisocyanates under microwave irradiation in molten ionic liquid

Ionic liquids (IL)s have been generating increasing attention over the last decade. ILs were originally introduced as alternative green reaction media owing to their distinctive chemical and physical properties of nonvolatility, nonflammability, thermal stability, and controlled miscibility. In this investigation, 5‐(4‐methyl‐2‐phthalimidyl‐pentanoylamino)isophthalic acid ( 6 ), as a bulky monomer, containing phthalimide and flexible chiral groups, has been synthesized. The direct polycondensation of this diacid monomer with several aromatic and aliphatic diisocyanates, such as 4,4′‐methylenebis(phenyl isocyanate), toluylene‐2,4‐diisocyanate, isophorone diisocyanate, and hexamethylene diisocyanate, was carried out in tetrabutylammonium bromide as a molten IL in the presence of different catalysts under microwave irradiation as well as conventional heating. The resulting polyamides (PA)s were characterized by FTIR and ¹H NMR spectroscopy, inherent viscosity measurements, thermal and elemental analysis. The obtained PAs showed high yields and moderate inherent viscosities in a range of 0.32–0.57 dL g⁻¹. The PAs were soluble in aprotic polar solvents. Thermogravimetric analysis showed that PAs are thermally stable, 10% weight loss temperatures in excess of 240 and 245°C, and char yields at 600°C in nitrogen higher than 14%. Since toxic and volatile solvent such as NMP was eliminated, this process was safe and green. It is very important to note that, because of high polarizability of ILs, they are very good solvents for absorbing microwaves. The combination of IL and microwave irradiation leads to large reductions in reaction times, very high heating rate with various benefits of the eco‐friendly approach, named green chemistry. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Poly(amide‐ester)s derived from dicarboxylic acid and aminoalcohol

A series of alternating aliphatic poly(amide‐ester)s, derived from dicarboxylic acid and aminoalcohols, were obtained by polycondensation in melt. All poly(amide‐ester)s were characterized by FTIR and ¹H/¹³C‐NMR spectroscopies. The synthesized polymers showed an inherent viscosity ranging from 0.4 to 1.0 dL g^?1. Thermal analysis showed melting points within the range 100–115°C and glass transition within the range 30–60°C. Decomposition temperatures were more than 200°C higher than the corresponding melting temperatures. The polymers can thus be processed from the melt. The processed polymers were partially crystalline with good thermal stability. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 95: 362–368, 2005     

Thermal stability,solubility, and fluorescence property of poly(arylene ether ketone)s bearing <Emphasis Type="Italic">N</Emphasis>-arylenebenzimidazole units

A series of novel random poly(arylene ether ketone)s containing N-arylenebenzimidazolyl groups with precise structures in high yields were synthesized from 2-(2′-hydroxyphenyl) benzimidazole and 4,4′-dihydroxybenzophenone with 4,4′-difluorobenzophenone via nucleophilic substitution polycondensation reaction using sulfolane as a solvent. The reaction was carried out at 210 °C in the presence of anhydrous potassium carbonate. The structures of the resulted polymers were characterized by means of FT-IR, ¹H NMR spectroscopy, and elemental analysis, and the results were largely consistent with the proposed structure. X-ray diffraction studies revealed that the incorporation of N-arylenebenzimidazolyl groups decreased the crystallinity of the resulted polymers. As the benzimidazole unit content in the copolymer increased, the solubility and thermal behavior of the prepared polymers improved. The novel poly(arylene ether ketone)s exhibited glass transition temperatures (T _gs) in the range 188–237°C, and there was a good linearity relationship between T _g values and the content of benzimidazolyl groups. The 5% decomposition temperatures were within the range of 512–539 °C in nitrogen and 496–540 °C in air indicating their good thermal stability. Tensile tests of the films showed that these polymers have desirable mechanical properties. Moreover, the resulting polymers showed good fluorescence properties.     

Synthesis and characterization of new imidazole and fluorene–bisphenol based polyamides: Thermal,photophysical and antibacterial properties

A new para-linked diether-diamine, 9,9-bis{4-[2-(4,5-diphenylimidazol-2-yl)-4-aminophenoxy] phenyl}fluorene (III), bearing fluorene–bisphenol and two ortho-linked diaryl-substituted imidazole rings were synthesized by the catalytic reduction of the nitro groups of compound (II), 9,9-bis{4-[2-(4,5-diphenylimidazol-2-yl)-4-nitrophenoxy]phenyl}fluorene, by using hydrazine monohydrate in the presence of Pd/C. Compound (II) was synthesized by the nucleophilic chloro displacement reaction of the synthesized 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole with 9,9-bis(4-hydroxyphenyl)fluorene in refluxing DMAc in the presence of potassium carbonate. This diamine was condensed directly with aliphatic and aromatic diacids via the Yamazaki–Higashi phosphorylation method in the presence of triphenylphosphite (TPP), pyridine (Py) and halide salt to give high molecular polyamides (PAs). The synthesized PAs were obtained in quantitative yields with inherent viscosities between 0.51 and 0.76 dL g^?1. The structures of diamine and PAs were characterized by elemental analysis, FT-IR and NMR spectroscopy, and properties of PAs were investigated by using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and UV–visible and fluorescence spectroscopy. The PAs showed good solubility in aprotic and polar organic solvents, with high thermal stability exhibiting the glass transition temperatures (T_gs) and 10% weight loss temperatures (T_10%) in the range of 226–330 °C and 400–466 °C in air, respectively, and fluorescence emission with maximum wavelengths (λ_em) in the range of 417–473 nm with quantum yields (Φ_f) of 9–35%. Two of these polymers together with compounds (II) and (III) were also screened for antibacterial activity against Gram positive and Gram negative bacteria.     

Synthesis and characterization of novel aromatic polyamides bearing CF3, quinoxaline‐anthraquinone pendants: Study of photophysical and electrochemical properties by using nanocomposite electrode paste

A new aromatic diamine, 2,3‐bis(4‐(4‐amino‐2‐(trifluoromethyl) phenoxy)phenyl)naphtho[2,3‐f]quinoxaline‐7,12‐dione, was synthesized and fully characterized by using FTIR, ¹H and ¹³C NMR, DEPT technique, and elemental analysis. A series of novel fluorescent anthraquinone‐quinoxaline containing polyamides (PAs) with inherent viscosities of 0.39–0.62 dL/g was prepared by direct polycondensation of the diamine with various dicarboxylic acids. These PAs were readily soluble in many polar aprotic organic solvents and could be solution‐cast into tough and flexible films. The PAs exhibited glass transition temperatures (T_g)s between 230 and 323°C, and 10% weight loss temperatures in the range of 362–433°C in N₂. All of the PAs have fluorescence emission in solution and in solid state with maxima around 452–510 nm and with the quantum yields in the range of 6–17%. Also, cyclic voltammetry (CV) method was used to study the electrochemical oxidation behavior of these polymers at the surface of a modified multiwalled carbon nanotube (MWCNT)s glassy electrode. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Novel poly(thiourea‐ether‐imide)s derived from 4,4′‐oxydiphenyl‐bis(thiourea): probing the possibility for high‐temperature applications

Our interest in the fabrication of high‐performance polyimides has led to thiourea‐substituted poly(thiourea‐ether‐imide)s (PTEIs) with good retention of thermal properties along with flame retardancy. A new aromatic monomer, 4,4′‐oxydiphenyl‐bis(thiourea) (ODPBT), was efficiently synthesized and polymerized with various dianhydrides (pyromellitic dianhydride, 3,3′,4,4′‐benzophenonetetracarboxylic dianhydride and 4,4′‐(hexafluoroisopropylidene)diphthalic dianhydride) via two‐stage chemical imidization to fabricate a series of PTEIs. The structural characterization of ODPBT and the polymers was carried out using Fourier transform infrared, ¹H NMR and ¹³C NMR spectral techniques along with crystallinity, organosolubility, inherent viscosity and gel permeation chromatographic measurements. PTEIs bearing C?S and ? O? moieties in the backbone demonstrated an amorphous nature and were readily soluble in various amide solvents. The novel polymers had inherent viscosities of 1.16–1.23 dL g^?1 and molecular weights of ca 90 783–96 927 g mol^?1. Their thermal stability was substantiated via 10% weight loss in the temperature range 516–530 °C under inert atmosphere. The polyimides had glass transition temperatures of 260–265 °C. Incorporation of thiourea functionalities into polymer backbones is demonstrated to be an effective way to enhance their thermal properties and flame retardancy. Thus, ODPBT can be considered as an excellent candidate for use in the synthesis of high‐performance polymeric materials. Copyright © 2010 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     

Synthesis and characterization of new polyamides and polyimides containing dioxypyrimidine moiety in the main chain with bulky imidazole pendent group: solubility, thermal and photophysical properties

A new symmetrical diamine monomer containing dioxypyrimidine and two diaryl imidazole bulky pendent group was synthesized by the nucleophilic substitution reaction of 4,6 dihydroxy pyrimidine with the synthesized 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole (I). A series of novel fluorescent imidazole-containing polyamides (PAs) with inherent viscosities of 0.52–0.78 dL/g was prepared by direct polycondensation of the diamine with various dicarboxylic acids. These PAs were readily soluble in many organic solvents and could be solution-cast into tough and flexible films. The PAs exhibited glass transition temperatures (T_g)s between 202 and 260 °C, and 10% weight loss temperatures in the range of 345–470 °C in air. In addition, three novel polyimides (PIs) with inherent viscosities of 0.38–0.56 dL/g were prepared by addition reaction of the diamine with commercially available tetracarboxylic dianhydrides and subsequent chemical imidization. The PIs exhibited good solubility in polar solvents such as NMP. These polymers exhibited T_gs in the range of 237–285 °C and their 10% weight-loss temperatures varied from 440 to 520 °C.     

Synthesis and characterization of new soluble polyamides from an unsymmetrical diamine bearing a bulky triaryl pyridine pendent group

New unsymmetrical diamine monomer containing triaryl pyridine pendent group, 2,4‐diaminophenyl [4‐(2, 6‐diphenyl‐4‐pyridyl) phenyl]ether, was synthesized via aromatic substitution reaction of 1‐chloro‐2,4‐dinitrobenzene with 4‐(2,6‐diphenyl‐4‐pyridyl) phenol, followed by Pd/C‐catalyzed hydrazine reduction. Five Polyamides (PA) were prepared by the phosphorylation polycondensation of different dicarboxylic diacids with the diamine. Inherent viscosities of PAs were in the range 0.51–0.59 g/dL indicating formation of medium molecular weight polymers. The weight and number average molecular weights of a PA, (PA‐d), determined by GPC were 6944 g/mol and 17,369 g/mol, respectively. PAs exhibited glass‐transition temperatures (T_g) in the range 140–235°C. These polymers, essentially amorphous, were soluble in polar aprotic solvents such as DMF, NMP, DMAc, DMSO, pyridine, m‐cresol, and THF. The initial decomposition temperatures (T_i) of PAs, determined by TGA in air, were in the range 300–380°C indicating their good thermal stability. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

<Emphasis Type="SmallCaps">l</Emphasis>-Aspartic acid incorporated optically active poly(amide-imide)s: synthesis and characterization

N-trimelliticimido-l-aspartic acid (1) was prepared from the reaction of trimellitic anhydride with l-aspartic acid in a mixture of glacial acetic acid and pyridine solution (3/2 ratio) under refluxing conditions. The solution polycondensation of the corresponding activated monomer with eight aromatic diamines were carried out in DMAc. The resulting poly(amide-imide)s were obtained in quantitative yields, showed admirable inherent viscosities (0.20–0.36 dl g⁻¹), good optical activity (+7.32o to +15.24o), and were readily soluble in polar aprotic solvents. They start to decompose (T _10%) above 170 °C and display glass-transition temperatures at 120–237 °C. All of the above polymers were fully characterized by UV, FT–IR, and ¹HNMR spectroscopy, elemental analysis, thermogravimetric analyses, DSC, inherent viscosity measurement, and specific rotation.     

Highly refractive and organo-soluble poly(amide imide)s based on 5,5′-thiobis(2-amino-4-methyl-thiazole): Synthesis and characterization

A new thioether-bridged diimide-diacid (DIDA) monomer was synthesized from the condensation of 5,5′-thiobis(2-amino-4-methyl-thiazole) (DA) and trimellitic anhydride at 1 : 2 molar ratio. A series of novel organic-soluble poly(amide imide)s (PAIs) bearing flexible thioether linkages and heteroaromatic thiazole groups were synthesized from DIDA with various commercially available aromatic diamines (1–5) via a direct polycondensation method with triphenyl phosphite and pyridine. The resulting polymers were obtained in high yields and possessed inherent viscosities in the range of 0.47–0.91 dL g^–1. All of the polymers were amorphous in nature, showed good solubility and could be easily dissolved in amide-type polar aprotic solvents (e.g., N-methyl-2-pyrrolidone, dimethyl sulfoxide, and N,N-dimethylacetamide), and even dissolved in less polar solvents (e.g., pyridine and tetrahydrofuran). They showed excellent thermal stability with glass transition temperatures between 233–269°C and 10% weight loss temperatures in excess of 480°C in nitrogen and 450°C in air atmosphere. The flexible structure endowed the PAI films with good optical transparency. The optical transmittances of the PAI films at 450 nm were higher than 80% for the thickness of approximately 10 μm. Moreover, the thiazole moieties and flexible thioether linkages in the molecular chains of the PAIs provided them with high refractive indices of 1.7329–1.7509 and low birefringences of 0.0065–0.0098. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis and characterization of novel aromatic-aliphatic poly(amide-imide-imide)s (PAII)

Novel poly(amide-imide-imide)s (PAII) were prepared by polycondensation of a new monomer synthesized from trimellitic anhydride and glutamic acid, followed by reflux condensing with thionyl chloride and several diamines. Polymers and monomers were characterized by ¹H NMR and FT-IR spectroscopy, elemental analysis and mass spectrometry. Inherent viscosities of the resulting polymers were in the range of 17–26 mL g^–1 (M_w 13 400–29 160, polydispersity (M_w/M_n) ca. 1.3–1.7), representing rather low molecular weights. The glass transition temperatures of the polymers were in the range of 210–285°C depending on the structure of diamines, and the thermal stability of the polymers was up to 400°C, comparable with that of polyimides and poly(amide imide)s. All the polymers synthesized are well soluble in aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone and dimethylacetamide. Particularly, polymers containing oxydianiline and 4,4′-diaminodiphenyl sulfone were quite soluble in m-cresol, pyridine, nitrobenzene and tetrahydrofuran.     

Synthesis and properties of aromatic polyimide,poly(benzoxazole imide), and poly(benzoxazole amide imide)

Two series of heterocyclic aromatic polymers were synthesized from 4,4′‐(4,4′‐isopropylidenediphenoxy)bis(phthaltic anhydride) and 2,2′‐bis(3,4‐dicarboxyphenyl)hexafluoropropane dianhydride by two‐step method. The inherent viscosities were in the range of 24–45 cm³/g. The effects of the rigid benzoxazole group in the backbone of copolymer on the thermal, mechanical, and physical properties were investigated. These polymers exhibit good thermal stability. The temperatures of 5% weight loss (T₅) of these polymers are in the range of 403–530°C in air and 425–539°C in nitrogen. The chard yields of these polymers are in the range of 15–24% in air and 54–61% in nitrogen. These polymers also have high glass‐transition temperatures and a low coefficient of thermal expansion and good mechanical properties. The poly(benzoxazol imide) has a higher tensile strength and modulus than those of neat polyimide. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Synthesis and identification of organosoluble polyamides bearing a triaryl imidazole pendent: Thermal,photophysical, chemiluminescent,and electrochemical characterization with a modified carbon nanotube electrode

A novel monomer containing a triaryl imidazole pendent group was successfully synthesized by nucleophilic substitution of bisphenol A with 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole (I). A series of new polyamides (PAs) with inherent viscosities of 0.95–1.2 dL/g was prepared by direct polycondensation of the diamine with various dicarboxylic acids. These PAs were readily soluble in many organic solvents and gave tough and flexible films by solution casting. These PAs exhibited T_gs between 189 °C and 252 °C, and 10% weight loss temperatures in excess of 400 °C with up to 68% char yield at 600 °C in air. All of the PAs emitted a greenish-yellow light in dilute THF solution, with photoluminescence (PL) quantum yields in the range of 10–25%. The chemiluminescent activity and electrochemical oxidation of the PAs were also investigated.     

Polyamides obtained by direct polycondesation of 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl] fluoren‐9‐YL]‐2‐methyl‐phenoxy]aniline with dicarboxylic acids based on a diphenyl‐silane moiety

Polyamides (PAs) containing fluorene, oxyether, and diphenyl‐silane moieties in the repeating unit were synthesized in > 85% yield by direct polycondesation between a diamine and four dicarboxylic acids. Alternatively, one PA was synthesized from an acid dichloride. The diamine 4‐[4‐[9‐[4‐(4‐aminophenoxy)‐3‐methyl‐phenyl]fluoren‐9‐yl]‐2‐methyl‐phenoxy]aniline ( 3 ) was obtained from the corresponding dinitro compound, which was synthesized by nucleophilic aromatic halogen displacement from p‐chloronitrobenzene and 9,9‐bis (4‐hydroxy‐3‐methyl‐phenyl)fluorene ( 1 ). Monomers and polymers were characterized by FTIR and ¹H, ¹³C, and ²⁹Si‐NMR spectroscopy and the results were in agreement with the proposed structures. PAs showed inherent viscosity values between 0.14 and 0.43 dL/g, indicative of low molecular weight species, probably of oligomeric nature. The glass transition temperature (T_g) values were observed in the 188–211°C range by DSC analysis. Thermal decomposition temperature (TDT_10%) values were above 400°C due to the presence of the aromatic rings in the diamine. All PAs showed good transparency in the visible region (>88% at 400 nm) due to the incorporation of the fluorene moiety. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Synthesis and characterization of novel poly(phenylene sulfide) containing a chromophore in the main chain

A kind of novel poly(phenylene sulfide)s (PPSs) containing a chromophore group were synthesized by the reaction of dihalogenated monomer and sodium sulfide (Na₂S.xH₂O) via nucleophilic substitution polymerization under high pressure. The polymers were characterized by Fourier transform infrared spectroscopy, ultraviolet spectroscopy, fluorescence spectroscopy, XRD, DSC, TGA, mechanical testing and dissolvability experiments. The intrinsic viscosity of the polymers obtained with optimum synthesis conditions was 0.22 ? 0.38 dl g^?1 (measured in 1‐chloronaphthalene at 208 °C). These polymers were found to have good thermal performance with a glass transition temperature (T_g) of 90.5 ? 94.6 °C and initial degradation temperature (T_d) of 475–489 °C, showing improved thermal properties compared with homo‐PPS. At the same time the resultant resins had a high tensile strength of 67.5 ? 74.1 MPa and compressive strength of 70.7 ? 85.4 MPa. Additionally, these polymers exhibited a weak UV ? visible reflectivity minimum at 450–570 nm, and the fluorescence spectra of the polymers showed maximum emission around nearly 370 nm. Also they showed excellent chemical resistance and another special property ? bright shiny colors changed into different colors in acid solution. © 2014 Society of Chemical Industry     

High‐optical transparency and low‐dielectric constant of new organosoluble polyamides containing trifluoromethyl and xanthene groups

A series of fluorinated polyamides was prepared directly by low‐temperature polycondensation of a new cardo diacid chloride, 9,9‐bis[4‐(4‐chloroformylphenoxy)phenyl]xanthene (BCPX), with various diamines containing trifluoromethyl substituents in N,N‐dimethylacetamide (DMAc). Almost all polyamides showed excellent solubility in amide‐type solvents such as DMAc and could also be dissolved in pyridine, m‐cresol, and tetrahydrofuran. These polymers had inherent viscosities between 0.77 and 1.31 dL g^?1, and their weight‐average molecular weights and number‐average molecular weights were in the range of 69,000–102,000 and 41,000–59,000, respectively. The resulting polymers showed glass transition temperatures between 240–258°C and 10% weight loss temperatures ranging from 484°C to 517°C and 410°C to 456°C in nitrogen and air, respectively, and char yields at 800°C in nitrogen higher than 55%. All polymers were amorphous and could be cast into transparent, light‐colored, and flexible films with tensile strengths of 81–100 MPa, elongations at break of 8–12%, and tensile modulus of 1.6–2.1 GPa. These polymers had low‐dielectric constants of 3.34–3.65 (100 kHz), low‐moisture absorption in the range of 0.76–1.91%, and high transparency with an ultraviolet–visible absorption cut‐off wavelength in the 322–340 nm range. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Synthesis and characterization of novel polyimides derived from 4,4’-bis(5-amino-2-pyridinoxy)benzophenone: effect of pyridine and ketone units in the main

A diamine monomer, 4,4’-bis(5-amino-2-pyridinoxy)benzophenone, was designed and synthesized, and used to react with commercially different kinds of aromatic dianhydrides to prepare a series of polyimides containing pyridine and ketone units via the classical two-step procedure. Glass transition temperatures (T_g) of the resultant polyimides PI-(1–5) derived from 4,4’-bis(5-amino-2-pyridinoxy) benzophenone with various dianhydrides ranged from 201 to 310 °C measured by differential scanning calorimetry. The temperatures for 5%wt loss of the resultant polyimides in nitrogen atmosphere obtained from the thermogravimetric analysis curves fell in the range of 472–501 °C. The temperatures for 10%wt loss of the resultant polyimides in nitrogen atmosphere fell in the range of 491–537 °C. Meanwhile, the char yields at 800 °C were in the range of 55.3–60.8%. Moreover, the moisture absorption of polyimide films was measured in the range of 0.37–2.09%. The thin films showed outstanding mechanical properties with tensile strengths of 103–145 MPa, an elongation at break of 12.9–15.2%, and a tensile modulus of 1.20–1.88 Gpa, respectively. The coefficients of thermal expansion of the resultant polyimides were obtained among 26–62 ppm °C^?1. To sum up, this series of polyimides had a good combination of properties applied for high-performance materials and showed promising potential applications in the fields of optoelectronic devices.