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.     

Aromatic polyesters containing pendent 4-(phenylsulfonyl)phenyl groups: synthesis and characterization

A new bisphenol, 1,1-bis-[(4-hydroxyphenyl)-1-(4-phenylsulfonyl)phenyl)]ethane (DPSBP) was synthesized starting from diphenylsulfide and was characterized by spectroscopic methods. DPSBP was polycondensed with isophthalic acid chloride (IPC), terephthalic acid chloride (TPC) and a mixture of IPC and TPC (50:50 mol%) by phase-transfer catalysed interfacial polymerization method to obtain aromatic polyesters containing pendent 4-(phenylsulfonyl)phenyl groups. A series of copolyesters was also obtained by polycondensation of varying molar proportions of DPSBP and bisphenol-A (BPA) with TPC. (Co)polyesters exhibited inherent viscosities in the range 0.56–1.57 dLg^?1 and number average molecular weights (Mn) were in the range 28,650–80,230 g/mol. Polyesters dissolved readily in common organic solvents such as dichloromethane, chloroform, tetrahydrofuran and aprotic polar solvents such as N-methylpyrrolidone, and N,N-dimethylacetamide. Tough, transparent and flexible films of polyesters could be cast from their chloroform solutions. X-Ray diffraction studies indicated amorphous nature of aromatic polyesters. Polyesters showed T_g values in the range 223–257 °C while T₁₀ values were in the range of 469–484 °C indicating their excellent thermal stability.     

Synthesis and characterization of new aromatic polyesters containing pendent naphthyl units

Two bisphenols, viz., 4,4′‐[1‐(2‐naphthalenyl)ethylidene]bisphenol and 4,4′‐[1‐(2‐naphthalenyl) ethylidene]bis‐3‐methylphenol were prepared by condensation of commercially available 2‐acetonaphthanone with phenol and o‐cresol, respectively. A series of new aromatic polyesters containing pendent naphthyl units was synthesized by phase‐transfer‐catalyzed interfacial polycondensation of these bisphenols with isophthaloyl chloride, terephthaloyl chloride, and a mixture of isophthaloyl chloride/terephthaloyl chloride (50 : 50 mol %). Inherent viscosities of polyesters were in the range 0.83–1.76 dL g⁻¹, while number average molecular weights (M_n) were in the range 61,000–235,000 g mol⁻¹. Polyesters were readily soluble in organic solvents such as dichloromethane, chloroform, tetrahydrofuran, m‐cresol, pyridine, N,N‐dimethylformamide, N,N‐dimethylacetamide, and 1‐methyl‐2‐pyrrolidinone at room temperature. Tough, transparent, and flexible films were cast from a solution of polyesters in chloroform. X‐Ray diffraction measurements displayed a broad halo at 2θ ≅ 19° indicating the amorphous nature of polyesters. Glass transition temperatures of polyesters were in the range 209–259°C. The temperature at 10% weight loss (T₁₀), determined by TGA in nitrogen atmosphere, of polyesters was in the range 435–500°C indicating their good thermal stability. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

High molecular weight poly(p-arylene sulfide ketone): synthesis and membrane-forming properties

High-molecular-weight poly(p-arylene sulfide ketone) (PPSK) was prepared by nucleophilic substitution reaction of 4,4’-diflurobenzophenone (DFBP) and sodium sulfide in the compound solvents of diphenyl sulfone (DPS) and 1,3-dimethyl-2-imidazolidinone (DMI) with catalysts under elevated temperature. The inherent viscosity (η_int) of the PPSK synthesized was 0.703 dl/g. PPSK was characterized by Fourier-transform infrared spectroscopy, elemental analysis, x-ray diffraction, differential scanning calorimetry, and thermogravimetric analysis. It was found that the polymer had excellent thermal properties: glass transition temperature (T_g) was 142.8 °C, melting temperature (T_m) was 362.3 °C. Under nitrogen atmosphere, 5 % (T_5%) and 10 % (T_10%) weight-loss temperatures were about 498.5 °C and 526.2 °C, respectively, while in the air the T_5% and T_10% were about 517 °C and 535.8 °C, respectively. The PPSK was found to be a semi-crystalline polymer, as confirmed by XRD. The polymer was insoluble in any solvent except concentrated sulfuric acid at room temperature. A series of the PPSK separating membranes were prepared by dissolving PPSK to concentrated sulfuric acid. The fluxes and the porosities of the separating membranes were in the range of 230–43 L/(m²?·?h) and 77.7-84.7 %, respectively. At the same time, these separating membranes showed moderate tensile strength of 1.02-1.88 MPa.     

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     

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.     

Synthesis and characterization of novel poly(amide-ether)s bearing imidazole pendants: study of physical and optical properties

Two new para-linked diether-diamines, bis(4-(4-amino-2-(4,5-diphenyl-1H-imidazol-2-yl)phenoxy) phenyl)methanone and bis(4-(4-amino-2-(4,5-diphenyl-1H-imidazol-2-yl)phenoxy) phenyl)hexafluoropropane, bearing two ortho-linked phenyl-substituted imidazole pendants and trifluoromethyl groups were synthesized by the nucleophilic chlorodisplacement reaction of the synthesized 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole with 4,4′-dihydroxybenzophenone or 4,4′-(hexafluoroisopropylidene)diphenol in refluxing DMAc in the presence of potassium carbonate. These diamines were utilized to prepare a series of novel poly(amide-ether)s (PAEs) via direct phosphorylation polycondensation with aliphatic and aromatic dicarboxylic acids. The polymeric samples were readily soluble in a variety of organic solvents and formed low-colored and flexible thin films via solution casting. These polymers showed glass-transition temperatures (T _gs) between 204 and 308 °C. Thermal behaviors of the PAEs were characterized by thermogravimetric analysis, and the 10 % weight loss temperatures were found to be in the range of 330–450 °C in N₂. The PAEs exhibited fluorescence emission in solution and in solid state with maxima around 423–494 nm and with the quantum yields in the range of 6–28 %.     

Synthesis and characterization of polyesters based on 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane

Aromatic polyesters are of considerable interest because of their excellent mechanical properties, chemical resistance and thermal stability. However, most aromatic polyesters are difficult to process due to their high glass transition temperatures coupled with their insolubility in common organic solvents. The present article describes a series of organosoluble polyesters and copolyesters based on 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane. A series of new aromatic polyesters containing pendant pentadecyl chains was synthesized by interfacial polycondensation of 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC. A series of copolyesters was synthesized from 4,4′‐isopropylidenediphenol with TPC by incorporating 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane as a comonomer. Inherent viscosities of the polyesters and copolyesters were in the range 0.72–1.65 dL g^?1 and number‐average molecular weights were in the range 18 170–87 220. The polyesters and copolyesters containing pendant pentadecyl chains dissolved readily in organic solvents such as chloroform, dichloromethane, pyridine and m‐cresol and could be cast into transparent, flexible and apparently tough films. Wide‐angle X‐ray diffraction data revealed the amorphous nature of the polyesters and copolyesters. The formation of loosely developed layered structure was observed due to the packing of pendant pentadecyl chains. The temperature at 10% weight loss, determined using thermogravimetric analysis in nitrogen atmosphere, of the polyesters and copolyesters containing pendant pentadecyl chains was in the range 400–460 °C. The polyesters and copolyesters exhibited glass transition temperatures in the range 63–82 °C and 177–183 °C, respectively. Copyright © 2010 Society of Chemical Industry     

Aromatic polyesters (polyarylates) containing arylene sulfone ether linkages

A series of soluble aromatic polyesters (polyarylates) containing arylene sulfone ether linkages and having inherent viscosities of 0.36–1.10 dl/g were prepared by the two-phase low temperature polycondensation of 4,4′-[sulfonyl-bis(p-phenyleneoxy)]dibenzoyl chloride and 3,3′-[sulfonylbis(p-phenyleneoxy)]-dibenzoyl chloride with various bisphenols in an organic solvent-aqueous alkaline solution system in the presence of a phase transfer catalyst. Bisphenols 4,4′-[sulfonylbis(p-phenyleneoxy)]diphenol and 3,3′-[sulfonylbis(p-phenyleneoxy)]-diphenol were synthesized in quantitative yields by an improved procedure. The aromatic polyesters prepared were characterized by infrared spectroscopy, elemental analysis, solution viscosity, thermogravimetric analysis, differential scanning calorimetry and X-ray diffraction. The polyesters prepared had glass transition temperatures in the range 150–230°C and initial decomposition temperatures of 397–491°C. They gave transparent, tough and flexible films by the solution casting technique.     

Sugar-based bicyclic monomers for aliphatic polyesters: a comparative appraisal of acetalized alditols and isosorbide

Three series of polyalkanoates (adipates, suberates and sebacates) were synthesized using as monomers three sugar-based bicyclic diols derived from D-glucose (Glux-diol and isosorbide) and D-mannose (Manx-diol). Polycondensations were conducted in the melt applying similar reaction conditions for all cases. The aim was to compare the three bicyclic diols regarding their suitability to render aliphatic polyesters with enhanced thermal and mechanical properties. The ensuing polyesters had molecular weights (M_w) in the 25,000–50,000 g mol^?1 range with highest values being attained for Glux-diol. All the polyesters started to decompose above 300 °C and most of them did not display perceivable crystallinity. On the contrary, they had glass transition temperatures much higher than usually found in homologous polyesters made of alkanediols, and showed a stress–strain behavior consistent with their T_g values. Glux-diol was particularly effective in increasing the T_g and to render therefore polyesters with high elastic modulus and considerable mechanical strength.     

Synthesis and characterization of novel organosoluble polyesters based on a DIOL with azaquinoxaline ring

A series of new polyesters were synthesized by polycondensation of aliphatic and aromatic dicarboxylic dichlorides with a novel quinoxaline diol, 2,3‐bis (4‐hydroxy phenyl)‐5‐azaquinoxaline (DIOL). The DIOL was synthesized by reacting 4,4′‐dihydroxy benzil with 2, 3‐diaminopyridine (yield: 85%), and characterized by FTIR and ¹H‐NMR spectra. All polyesters showed good solubility in most aprotic polar solvents such as NMP (N‐methylpyrrolidone), DMF (dimethylformamide), DMSO (dimethylsulfoxide), DMAc (dimethylacetamide), HMPA (hexamethylenephosphoramide), and Py (pyridine). The inherent viscosity of polyesters was obtained in the range of 1.1–1.22 dL/mg. The glass transition temperatures of the polyesters were in the range of 200–280°C, as determined by DSC. The initial decomposition temperatures of the polyesters were above 300°C and the char yield at 750°C ranged from 30 to 60% under nitrogen atmosphere. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Synthesis of highly soluble and transparent polyimides

A novel aromatic diamine, 3,3′‐diisopropyl‐4,4′‐diaminophenyl‐4″‐methyltoluene with a 4‐methylphenyl pendant group and isopropyl side groups, was designed and synthesized in this study. Then it was polymerized with various aromatic dianhydrides including pyromellitic dianhydride, 3,3′,4,4′‐biphenyltetracarboxylic dianhydride, 4,4′‐oxydiphthalic anhydride, 3,3′,4,4′‐benzophenone tetracarboxylic dianhydride and 4,4′‐(hexafluoroisopropylidene)diphthalic anhydride via a one‐pot high temperature polycondensation procedure to produce a series of aromatic polyimides. These polyimides exhibited excellent solubility even in common organic solvents, such as chloroform and tetrahydrofuran. The flexible and tough films can be conveniently obtained by solution casting. The films were nearly colorless and exhibited high optical transparency, with the UV cutoff wavelength in the range 302–365 nm and the wavelength of 80% transparency in the range 385–461 nm. Moreover, they showed low dielectric constants (2.73–3.23 at 1 MHz) and low moisture absorption (0.13%–0.46%). Furthermore, they also possessed good thermal and thermo‐oxidative stability with 10% weight loss temperatures (T_10%) in the range 489–507 °C in a nitrogen atmosphere. The glass transition temperatures of all polyimides are in the range 262–308 °C. Copyright © 2012 Society of Chemical Industry     

Synthesis and properties of copolymers of poly(ether ether sulfone)/semiaromatic polyamides (PEES/PA)

Poly(ether ether sulfone) (PEES) containing semi‐aromatic polyamides with methylene units and ether linkage were synthesized through the copolymerization of m‐dihydroxybenzene, 4,4‐dichlorodiphenylsulfone (DCDPS) and 1,6‐N, N′‐bis(4‐fluorobenzamide) hexane (BFBH) by the method of nucleophilic polymerization. The inherent viscosities of the resultant different proportion of copolymers were in the range of 0.39–0.78 dL/g. These copolymers were found to have excellent thermal properties with glass transition temperatures (T_g) of 121–177°C, and initial degradation temperatures (T_d) of 417.5–432.5°C. These copolymers showed good mechanical properties with tensile strengths of 45–83 MPa, storage modulus of 1.8–2.6 GPa. The complex viscosities of pure Poly(ether ether sulfone) (PEES) was in the range of 176,000–309.8 Pas from 0.01 to 100 Hz, the complex viscosities of the copolymers decreased significantly with the increase of semi‐aromatic amide content, the copolymers of 20% decreased from 4371 to 142.4 Pas (from 0.01 to 100 Hz), and the copolymers of 70% dropped from 634.6 Pas to 55.97 Pas (from 0.01 Hz to 100 Hz). All copolymers exhibited non‐Newtonian and shear‐thinning behavior. These results suggested the resultant copolymers possess better melt flowability that is beneficial for the materials’ melt processing. POLYM. ENG. SCI., 56:44–50, 2016. © 2015 Society of Plastics Engineers     

Polyamide derived from 4,4′-thiobis(methylene)dibenzoyl chloride and aliphatic diamine: interfacial synthesis and characterization

A series of processable semi-aromatic polyamides containing thioether and methylene units were synthesized through the reaction of 4,4′-thiobis(methylene)dibenzoyl chloride and aliphatic diamine by the method of interfacial polycondensation. These polyamides had excellent thermal properties with glass transition temperatures (T _g) of 104.3–130.6 °C, melting temperatures (T _m) of 300.3–303.8 °C, and initial degradation temperatures (T _d) of 405.2–410.3 °C. They had wider processing windows than traditional semi-aromatic polyamides (such as PA6T can not be processed by melting) and can be processed by melting method. They had better tensile strengths of 57.6–64.1 MPa, low-temperature mechanical properties, low water absorption of 0.19–0.27 %, low dielectric constants of 3.11–3.95 at 100 kHz, and better melt flowability properties of 232–60.7, 301.9–78.8, and 423.1–83.6 Pa s under a shear rate ranging from 20 to 1,170 s^?1, respectively. In addition, these polyamides showed good corrosion resistance, they did not dissolve in solvents such as NMP, DMSO, hydrochloric acid (6 mol/l), and solution of NaOH (1 mol/l) and so on.     

A new semicrystalline reinforced polyamide engineering thermoplastic

A new rapidly crystallizing aromatic-aliphatic polyamide has been developed by reacting 4,4′-methylene bis(phenylisocyanate) (MDI) with aliphatic dicarboxylic acids. The polymer has a T_g of 130°C and T_m, of 290°C. Glass reinforced resin shows better flexural creep resistance at high stress levels (3000 psi) at elevated temperatures (75°C) than most reinforced semicrystalline commercial polymers i.e., nylons, thermoplastic polyesters and acetal because of its high T_g. Glass reinforced polyamide can be injection molded on conventional equipment to afford flexural moduli in excess of 1,000,000 psi and HDT's as high as 250°C at 264 psi. Because of the high level of crystallinity these parts will not dissolve or swell in most organic solvents and this aromatic aliphatic polyamide is also far less sensitive to moisture than commercial nylons.     

Synthesis and characterization of new unsaturated polyesters containing cyclopentapyrazoline moiety in the main chain

3‐p‐Hydroxyphenyl‐6‐p‐hydroxybenzylidene cyclopentapyrazoline (III) and 3‐vanillyl‐7‐vanillylidene cyclopentapyrazoline (IV) were used as new starting materials for preparing new unsaturated polyesters. The polyesters were prepared by reacting (III) or (IV) with adipoyl, sebacoyl, isophthaloyl, and terephthaloyl dichlorides utilizing the interfacial polycondensation technique. The polyester samples have been characterized by elemental and spectral analyses. The polyesters have inherent viscosities of 0.55–0.97 dL/g. All the polyesters are semicrystalline and most of them are partially soluble in most common organic solvents but freely soluble in concentrated sulfuric acid. Their glass transition temperatures (T_g) range from 103.34 to 208.81°C, and the temperatures of 10% weight loss as high as 190 to 260°C in air, indicating that these aromatic polyesters have high T_g and excellent thermal stability. Doping with iodine dramatically raised the conductivity and produced dark brown colored semiconductive polymers with a maximum conductivity in the order of 3.1 × 10^?7 Ω^?1 cm^?1. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Synthesis,characterization, and structure-property relationships of aromatic polyimides containing 4,4′-diaminotriphenylmethane

This work reports two series of structurally different aromatic polyimides based on 4,4´-diaminodiphenylmethane (DPM) and 4,4´-diaminotriphenylmethane (TPM) and three commercial dianhydrides. All TPM-based polyimides formed membranes due to their high molecular weight (inherent viscosities ~0.93–1.14 dl/g), they exhibited high thermal stability (5 %: 490–544 °C), glass transition temperatures between 269 and 293 °C, and reasonable mechanical properties. The incorporation of pendant phenyl moieties in the TPM-based polyimides has a strong effect producing an improvement in solubility, thermal stability, density and gas permeability coefficient in comparison with DPM-based polyimides. The most interesting polyimide TPM-6FDA, containing phenyl and trifluoromethyl as bulky pendant groups, showed higher gas permeability coefficient for CO₂ (23.73 Barrer) and the best ideal selectivity to the gas pair CO₂/CH₄ (α = 28.93).     

Investigations on the curing of epoxides with phthalic anhydride

The anhydride curing of epoxides was studied by performing copolymerizations of epichlorohydrin, phenyl glycidyl ether (PGE), or bisphenol-A-diglycidyl ether (BADGE) with phthalic anhydride (PSA). As initiators, tertiary amines or ammonium salts were used. In the case of epichlorohydrin, linear polyesters were obtained at 100°C. At higher temperatures (140–160°C), a side reaction of the CH₂Cl group took place which caused branching and partial crosslinking of the polymer. The reaction of phenyl glycidyl ether with phthalic anhydride gave linear, strongly alternating copolymers at temperatures of 120–160°C. Molecular weights (M¯_n) were in the range of 4000–87,000, depending on the purity of the starting materials and the initiator used. The reaction of the diepoxide BADGE with phthalic anhydride yielded highly crosslinked products. Their crosslink densities (which correlate with the glass transition temperature T_g). however, did not show the same dependence on initiator and purity of the starting materials as the molecular weights of the linear polyesters obtained by the “model reaction” of PGE with PSA. Possible reasons for this effect are discussed.     

Synthesis and characterization of organosoluble and transparent polyimides derived from trans‐1,2‐bis(3,4‐dicarboxyphenoxy)cyclohexane dianhydride

A novel dianhydride, trans‐1,2‐bis(3,4‐dicarboxyphenoxy)cyclohexane dianhydride (1,2‐CHDPA), was prepared through aromatic nucleophilic substitution reaction of 4‐nitrophthalonitrile with trans‐cyclohexane‐1,2‐diol followed by hydrolysis and dehydration. A series of polyimides (PIs) were synthesized from one‐step polycondensation of 1,2‐CHDPA with several aromatic diamines, such as 2,2′‐bis(trifluoromethyl)biphenyl‐4,4′‐diamine (TFDB), bis(4‐amino‐2‐trifluoromethylphenyl)ether (TFODA), 4,4′‐diaminodiphenyl ether (ODA), 1,4‐bis(4‐aminophenoxy)benzene (TPEQ), 4,4′‐(1,3‐phenylenedioxy)dianiline (TPER), 2,2′‐bis[4‐(3‐aminodiphenoxy)phenyl]sulfone (m‐BAPS), and 2,2′‐bis[4‐(4‐amino‐2‐trifluoromethylphenoxy)phenyl]sulfone (6F‐BAPS). The glass transition temperatures (T_gs) of the polymers were higher than 198°C, and the 5% weight loss temperatures (T_d5%s) were in the range of 424–445°C in nitrogen and 415–430°C in air, respectively. All the PIs were endowed with high solubility in common organic solvents and could be cast into tough and flexible films, which exhibited good mechanical properties with tensile strengths of 76–105 MPa, elongations at break of 4.7–7.6%, and tensile moduli of 1.9–2.6 GPa. In particular, the PI films showed excellent optical transparency in the visible region with the cut‐off wavelengths of 369–375 nm owing to the introduction of trans‐1,2‐cyclohexane moiety into the main chain. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42317.     

Synthesis and characterization of polyimides from 4,4′-(3-(<Emphasis Type="Italic">tert</Emphasis>-butyl)-4-aminophenoxy)diphenyl ether

A novel diamine 4,4′-(3-(tert-butyl)-4-aminophenoxy)diphenyl ether (4) was synthesized from 2-tert-butylaniline and 4,4′-oxydiphenol through iodination, acetyl protection, coupling reaction and deacetylation protection. Then some polyimides (PIs) were obtained by one-pot polycondensation of diamne 4 with several commercial aromatic dianhydrides respectively. They all exhibit enhanced solubility in organic solvents (such as NMP, DMF, THF and CHCl₃ etc.) at room temperature. Their number-average molecular weights are in the range of (2.1–3.7)?×?10⁴ g/mol with PDI from 2.25 to 2.74 by GPC. They can form transparent, tough and flexible films by solution-casting. The light transparency of them is higher than 90% in the visible light range from 400 nm to 760 nm and the cut-off wavelengths of UV–vis absorption are below 370 nm. They also display the outstanding thermal stability with the 5% weight loss temperature from 525 °C to 529 °C in nitrogen atmosphere. The glass transition temperatures (T _g s) are higher than 264 °C by DSC. XRD results demonstrate that these PIs are amorphous polymers with the lower water absorption (<0.66%). In summary, the incorporation of tert-butyl groups and multiple phenoxy units into the rigid PI backbones can endow them excellent solubility and transparency with relatively high T _g s.