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Diamine Monomer (diamine + monomer)
Selected AbstractsHighly stable electrochromic polyamides based on N,N -bis(4-aminophenyl)- N,,N,-bis(4- tert -butylphenyl)-1,4-phenylenediamineJOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 9 2009Sheng-Huei Hsiao Abstract A new triphenylamine-containing aromatic diamine monomer, N,N -bis(4-aminophenyl)- N,,N,-bis(4- tert -butylphenyl)-1,4-phenylenediamine, was synthesized by an established synthetic procedure from readily available reagents. A novel family of electroactive polyamides with di- tert -butyl-substituted N,N,N,,N,-tetraphenyl-1,4-phenylenediamine units were prepared via the phosphorylation polyamidation reactions of the newly synthesized diamine monomer with various aromatic or aliphatic dicarboxylic acids. All the polymers were amorphous with good solubility in many organic solvents, such as N -methyl-2-pyrrolidinone (NMP) and N,N -dimethylacetamide, and could be solution-cast into tough and flexible polymer films. The polyamides derived from aromatic dicarboxylic acids had useful levels of thermal stability, with glass-transition temperatures of 269,296 °C, 10% weight-loss temperatures in excess of 544 °C, and char yields at 800 °C in nitrogen higher than 62%. The dilute solutions of these polyamides in NMP exhibited strong absorption bands centered at 316,342 nm and photoluminescence maxima around 362,465 nm in the violet-blue region. The polyamides derived from aliphatic dicarboxylic acids were optically transparent in the visible region and fluoresced with a higher quantum yield compared with those derived from aromatic dicarboxylic acids. The hole-transporting and electrochromic properties were examined by electrochemical and spectro-electrochemical methods. Cyclic voltammograms of the polyamide films cast onto an indium-tin oxide-coated glass substrate exhibited two reversible oxidation redox couples at 0.57,0.60 V and 0.95,0.98 V versus Ag/AgCl in acetonitrile solution. The polyamide films revealed excellent elcterochemical and electrochromic stability, with a color change from a colorless or pale yellowish neutral form to green and blue oxidized forms at applied potentials ranging from 0.0 to 1.2 V. These anodically coloring polymeric materials showed interesting electrochromic properties, such as high coloration efficiency (CE = 216 cm2/C for the green coloring) and high contrast ratio of optical transmittance change (,T%) up to 64% at 424 nm and 59% at 983 nm for the green coloration, and 90% at 778 nm for the blue coloration. The electroactivity of the polymer remains intact even after cycling 500 times between its neutral and fully oxidized states. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2330,2343, 2009 [source] Synthesis and properties of novel sulfonated polyimides containing binaphthyl groups as proton-exchange membranes for fuel cellsJOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 2 2007Yuhan Li Abstract A novel sulfonated diamine monomer, 2,2,-bis(p -aminophenoxy)-1,1,-binaphthyl-6,6,-disulfonic acid (BNDADS), was synthesized. A series of sulfonated polyimide copolymers containing 30,80 mol % BNDADS as a hydrophilic component were prepared. The copolymers showed excellent solubility and good film-forming capability. Atomic force microscopy phase images clearly showed hydrophilic/hydrophobic microphase separation. The relationship between the proton conductivity and degree of sulfonation was examined. The sulfonated polyimide copolymer with 60 mol % BNDADS showed higher proton conductivity (0.0945,0.161 S/cm) at 20,80 °C in liquid water. The membranes exhibited methanol permeability from 9 × 10,8 to 5 × 10,7 cm2/s at 20 °C, which was much lower than that of Nafion (2 × 10,6cm2/s). The copolymers were thermally stable up to 300 °C. The sulfonated polyimide copolymers with 30,60 mol % BNDADS showed reasonable mechanical strength; for example, the maximum tensile strength at break of the sulfonated polyimide copolymer with 40 mol % BNDADS was 80.6 MPa under high moisture conditions. The optimum concentration of BNDADS was found to be 60 mol % from the viewpoint of proton conductivity, methanol permeability, and membrane stability. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 222,231, 2007 [source] Novel aromatic polyamides and polyimides functionalized with 4- tert -butyltriphenylamine groupsJOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 15 2006Sheng-Huei Hsiao Abstract A new triphenylamine-containing diamine monomer, 4,4,-diamino-4,- tert -butyltriphenylamine, was successfully synthesized by the cesium fluoride-mediated N,N -diarylation of 4- tert -butylaniline with 4-fluoronitrobenzene, followed by the reduction of the nitro group. The obtained diamine monomer was reacted with various aromatic dicarboxylic acids and tetracarboxylic dianhydrides to produce two series of novel triphenylamine-based polyamides and polyimides with pendent tert -butyl substituents. Most of the polymers were readily soluble in polar organic solvents, such as N -methyl-2-pyrrolidone and N,N -dimethylacetamide (DMAc), and could be solution cast into tough and flexible polymer films. These polymers showed high glass transition temperatures between 282 and 320 °C, and they were fairly stable up to a temperature above 450 °C (for polyamides) or 500 °C (for polyimides). These polymers exhibited UV absorption maxima around 308 to 361 nm. The photoluminescence spectra of the polyamides in DMAc exhibited a peak emission wavelength in the blue at 421,433 nm. Cyclic voltammograms of polyamides and polyimides showed an oxidation wave at 1.0,1.1 V versus Ag/AgCl in an acetonitrile solution. All the polyamides and polyimides exhibited excellent reversibility of electrochromic characteristics by continuous several cyclic scans between 0.0 and 1.1,1.3 V, with a color change from the original pale yellowish neutral form to the green or blue oxidized forms. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 4579,4592, 2006 [source] Synthesis and properties of fluorinated polyimides based on 1,4-bis(4-amino-2-trifluoromethylphenoxy)-2,5-di- tert -butylbenzene and various aromatic dianhydridesJOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 9 2004Chin-Ping Yang Abstract A novel fluorinated diamine monomer, 1,4-bis(4-amino-2-trifluoromethylphenoxy)-2,5-di- tert -butylbenzene (2), was prepared through the nucleophilic substitution reaction of 2-chloro-5-nitrobenzotrifluoride and 2,5-di- tert -butylhydroquinone in the presence of potassium carbonate, followed by catalytic reduction with hydrazine and Pd/C. Fluorinated polyimides (5a,5f) were synthesized from diamine 2 and various aromatic dianhydrides (3a,3f) via thermal or chemical imidization. These polymers had inherent viscosities of 0.77,1.01 dL/g. The 5 series polyimides were soluble in N -methyl-2-pyrrolidone, N,N -dimethylacetamide, and N,N -dimethylformamide and were even soluble in dioxane, tetrahydrofuran, and dichloromethane. 5(C) showed cutoff wavelengths between 363 and 404 nm and yellowness index (b*) values of 6.5,40.2. The polyimide films had tensile strengths of 93,114 MPa, elongations to break of 9,12%, and initial moduli of 1.7,2.1 GPa. The glass-transition temperatures were 255,288 °C. The temperatures of 10% weight loss were all above 460 °C in air or nitrogen atmospheres. In comparison with a nonfluorinated polyimide series based on 1,4-bis(4-aminophenoxy)-2,5-di- tert -butylbenzene, the 5 series showed better solubility and lower color intensity, dielectric constants, and moisture absorption. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 2272,2284, 2004 [source] Novel Soluble Polyimide Containing 4- tert- Butyltoluene Moiety: Synthesis and CharacterizationCHINESE JOURNAL OF CHEMISTRY, Issue 11 2009Chenyi Wang Abstract Based on the synthesis of a rigid aromatic diamine, ,,, -bis(4-aminophenyl)-4-(t- butyl)toluene (1), a novel polyimide (PI) 3 was prepared from this diamine monomer and 4,4,-oxydiphthalic dianhydride via a one-step high-temperature polycondensation. FT-IR, 1H NMR and elemental analysis were used to investigate the chemical structures of 1 and 3. The results confirmed that they agreed with the proposed structures for both 1 and 3 completely. The obtained PI 3 showed excellent solubility in most common solvents such as N -methyl-2-pyrrolidinone, N,N -dimethylacetamide, N,N -dimethylformamide, chloroform, dichloromethane and tetrahydrofuran. The resulting strong and flexible film exhibited high thermal stability with the glass transition temperature at 317°C and the temperature at 10% weight loss beyond 519°C in both air and nitrogen atmospheres. Moreover, the film also showed high optical transparency, low dielectric constant (3.13 at 1 MHz), low water absorption (0.40%) and hydrophobic character. [source] Synthesis and characterization of Schiff-base-containing polyimidesJOURNAL OF APPLIED POLYMER SCIENCE, Issue 5 2010Mousa Ghaemy Abstract 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 [source] Preparation of poly(amic acid) and polyimide derived from 3,3,,4,4,-benzophenonetetracarboxylic dianhydride with different diamines by microwave irradiationJOURNAL OF APPLIED POLYMER SCIENCE, Issue 2 2008Quantao Li Abstract Polycondensation-type poly(amic acid) (PAA) was synthesized with 3,3,,4,4,-benzophenonetetracarboxylic dianhydride as a dianhydride monomer and 4,4,-diaminodiphenylmethane and 4,4,-oxydianiline as diamine monomers under microwave irradiation in dimethylformamide. Then, PAA was used to make polyimide (PI) by imidization at a low temperature. The structure and performance of the polymers were characterized with Fourier transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR), viscosity, X-ray diffraction (XRD), and thermogravimetry (TG) curve analyses. The FTIR spectra of the polymers showed characteristic peaks of PI around 1779 and 1717 cm,1. The 1H-NMR spectrum of PAA indicated a singlet at 6.55 ppm assigned to NHCO and a singlet at 10.27 ppm assigned to carboxylic acid protons. The XRD spectrum demonstrated that the obtained PI had a low-order aggregation structure with a d -spacing of 0.5453 nm. The TG results revealed that the PI was thermally stable with 10% weight loss at 565°C in an N2 atmosphere. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2008 [source] Structure,property correlations of sulfonated polyimides.JOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 14 2004Abstract A series of six-membered sulfonated polyimides were synthesized using 1,4,5,8-naphthalenetetracarboxylic dianhydride, 4,4,-diaminobiphenyl 2,2,-disulfonic acid as the sulfonated diamine, and various nonsulfonated diamine monomers having different bridging groups. These bulky bridging groups have the capacity to increase hydrolytic stability and proton conductivity. Polyimides with bulky bridging groups showed increased solubility but exhibited lower thermal stability. The ion exchange capacity and water uptake reduced with increase in the bulkiness of the bridging group. This was attributed to the increase in the molecular weight of the repeating unit and hence effectively reduced the sulfonic acid content. In low temperatures, the conductivity was lower than Nafion®115 and, with increase in temperature, the conductivity rapidly increased and exhibited better conductivity than Nafion®115. Polyimides with bulky bridging groups 4-amino phenyl sulfone, and 2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane showed higher conductivity than other polyimides and Nafion®115 despite low ion exchange capacity. The hydrolytic stability of the polyimides with bulky bridging groups was higher than the polyimides with less bulky atoms because of the imparted flexibility. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3612,3620, 2004 [source] Synthesis and Properties of 6FDA-MDA Copolyimide Membranes: Effects of Diamines and Dianhydrides on Gas Separation and Pervaporation PropertiesMACROMOLECULAR CHEMISTRY AND PHYSICS, Issue 24 2007Shude Xiao Abstract 6FDA-MDA-based polyimides were synthesized from a one-step polycondensation of 6FDA and MDA with other diamines and dianhydrides. The polyimides were characterized by GPC, FT-IR and NMR, and dense membranes were prepared from their solutions for gas separation and pervaporation. Gas separation and pervaporation properties were investigated using the linear moiety contribution method. The moiety contribution factors were used to analyze the effects of the dianhydride and diamine monomers on gas permselectivity and pervaporation permeation flux. It was shown that the steric effects and flexibility of the monomers and the interactions between the membrane and the penetrants accounted for the differences in separation properties. [source] | ||||||||||