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Faghihi Khalil,Hagibeygi Mohsen The Polymer Society of Korea 2005 Macromolecular Research Vol.13 No.1
Under irradiation in a microwave oven, six novel poly(amide-imide)s containing tetrahydropyrimidinone, tetrahydro-2-thioxopyrimidine moieties and trimellitic rings in their main chains were synthesized through the polycondensation reaction of N,N'-(4,4'-diphenylether)bis(trimellitimide) diacid chloride with six different derivatives of tetrahydropyrimidinone and tetrahydro-2-thioxopyrimidine in the presence of a small amount of a polar organic medium, such as o-cresol. The polycondensation proceeded rapidly and completed within 7-9 min, producing a series of new poly(amide-imide)s in high yield that showed inherent viscosities in the range 0.33-0.52 dL/g. These poly(amide-imide)s were characterized by elemental analysis, viscosity measurement, thermal gravimetric analysis, solubility test, and FT-IR spectroscopy. All of the polymers were soluble at room temperature in polar solvents such as N,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, and N-methyl-2-pyrrolidone.
Faghihi, Khalil,Shabanian, Meisam,Hajibeygi, Mohsen The Polymer Society of Korea 2009 Macromolecular Research Vol.17 No.11
An optically active diacid containing the L-histidine moiety was prepared by reacting pyromellitic dianhydride (1,2,4,5-benzenetetracarboxylic acid 1,2,4,5-dianhydride) 1 with L-histidine 2 in acetic acid, and was polymerized with several aromatic diamines 5a-g to obtain a new series of optically active poly(amide-imide)s (PAIs) using two different methods, such as direct polycondensation in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride ($CaCl_2$)/pyridine (Py) and direct polycondensation in a tosyl chloride (TsCl)/pyridine (Py)/N,N-dimethylformamide (DMF) system as a condensation agent. The resulting new polymers 6a-g with inherent viscosity was obtained in good yield. The polymers were readily soluble in polar organic solvents, such as N,N-dimethyacetamide (DMAc), N,N-dimethyformamide (DMF), and dimethyl sulfoxide (DMSO). The obtained polymers were characterized by FTIR, specific rotation, elemental analysis as well as $^1$H-NMR spectroscopy and gel permeation chromatography (GPC). The thermal stability of the resulting PAIs was evaluated with thermogravimetric analysis techniques under a nitrogen atmosphere.
Faghihi, Khalil,Hajibeygi, Mohsen,Shabanian, Meisam The Polymer Society of Korea 2009 Macromolecular Research Vol.17 No.10
N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g were synthesized by the condensation reaction of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride 1 with two equimolars of Lalanine 2a, L-valine 2b, L-leucine 2c, L-isoleucine 2d, L-phenyl alanine 2e, L-2-aminobutyric acid 2f and L-histidine 2g in an acetic acid solution. Seven new poly(amide-imide)s PAIs 5a-g were synthesized through the direct polycondensation reaction of seven chiral N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g with bis(3-amino phenyl) phenyl phosphine oxide 4 by two different methods: direct polycondensation in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride ($CaCl_2$/pyridine (py), and direct polycondensation in a tosyl chloride (TsCl)/pyridine (py)/N,N-dimethylformamide (DMF) system. The polymerization reaction produced a series of flame-retardant and thermally stable poly(amide-imide)s 5a-g with high yield. The resulted polymers were fully characterized by FTIR, $^1H$ NMR spectroscopy, elemental analyses, inherent viscosity, specific rotation and solubility tests. Data obtained by thermal analysis (TGA and DTG) revealed that the good thermal stability of these polymers. These polymers can be potentially utilized in flame retardant thermoplastic materials.
Faghihi, Khalil The Polymer Society of Korea 2004 Macromolecular Research Vol.12 No.3
We have developed facile and rapid polycondensation reactions of N-trimellitylimido-L-leucine diacid chloride 1 with eight different derivatives of hydantoin compounds 2a-h, in the presence of a small amount of a polar organic medium, such as Ο-cresol, by using a domestic microwave oven. The polycondensation reactions proceeded rapidly-they were complete within 7-9 min-to produce a series of novel optically active poly(amide-imide)s (3a-h) in high yield with inherent viscosities of 0.33-0.51 dL/g. We characterized the resulting poly(amide-imide)s by elemental analysis, thermal gravimetric analysis (DSC, TGA, and DTG), and FTIR spectroscopy, and by measuring their viscosities, specific rotations, and solubilities. All of the polymers were soluble at room temperature in polar solvents such as N ,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, and N-methyl-2-pyrrolidone.
Khalil Faghihi,Meisam Shabanian,Narjes Emamdadi 한국고분자학회 2010 Macromolecular Research Vol.18 No.8
A new series of aromatic poly(ester-imide)s (PEIs) 8a-f with 1,3-bis[4-aminophenoxy]propane moieties were prepared from the newly synthesized diacid monomer 6 with various aromatic diols 7a-f. The resulting polymers were fully characterized by Fourier transform infrared spectroscopy (FTIR) and 1H nuclear magnetic resonance spectroscopy (1H NMR), elemental analysis, inherent viscosity, solubility tests, thermogravimetric analysis (TGA),and derivative of thermogravimetric (DTG) analysis. The PEIs had inherent viscosity ranging from 0.18 to 0.90 dL/g and were soluble in common organic solvents, such as N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), N,N-dimethylformamide (DMF), and dimethyl sulfoxide (DMSO). They exhibited useful thermal properties associated with relatively moderate Tgs (210-220 oC), 10% weight loss temperatures in excess of 380 oC, and char yields at 800 oC in N2 of up to 29%. Dicarboxylic acid 6 was synthesized from the reaction of 1,3-bis[3-aminophenoxy]propane 4 with trimellitic anhydride 5 in a solution of glacial acetic acid/pyridine (Py) at the refluxing temperature. 1,3-Bis[4-nitrophenoxy]propane 3 was prepared by a reaction of 4-nitrophenol 1 with 1,3-dibromo propane 2 in a DMF solution. Dinitro 3 was reduced to diamine 4 using 10% Pd-C, ethanol and hydrazine monohydrate.
Khalil Faghihi,Meisam Shabanian 한국고분자학회 2010 Macromolecular Research Vol.18 No.12
A new series of poly(ether-amide)s (PEAs) containing flexible methylene segments in the main chain were synthesized through a direct polycondensation reaction of 1,4-(4-carboxy phenoxy)butane with five ethereal diamine derivatives in a medium containing N-methyl-2-pyrrolidone, triphenyl phosphite, calcium chloride, and pyridine. The resulting polymers were fully characterized by proton nuclear magnetic resonance spectroscopy (1H NMR), Fourier transform infrared (FTIR) spectroscopy, elemental analyses, inherent viscosity, and solubility tests. The thermal properties of the polymers were examined by thermal gravimetric analysis (TGA) and differential thermal gravimetric (DTG). The glass-transition temperatures of the PEAs were determined by differential scanning calorimetry (DSC). The diacid was prepared from a reaction of 4-hydroxy benzoic acid with 1,4-dibromo butane in the presence of NaOH. New ethereal diamines were synthesized by a two-step reaction. In the first step, dinitro compounds were prepared from a reaction of two equimolars 4-nitrophenol and one equimolar of dibromo compounds. The resulting dinitro compounds were then reduced using 10% Pd-C, ethanol and hydrazine monohydrate.
Khalil Faghihi,Mohammad Gholizadeh 한국고분자학회 2010 Macromolecular Research Vol.18 No.1
Six new poly(ester-imide)s 9a-f were prepared by the rapid polycondensation reaction of 1,3-bis[4,4'-bis(trimellitimidoyl chloride) phenyl]-2-propenone 7 with several aromatic diols 8a-f using a domestic microwave oven in the presence of a small amount of a polar organic medium, such as o-cresol. The polycondensation reaction proceeded more rapidly than solution polycondensation and was almost complete within 13 min, giving a series of poly(amide-imide)s in high yield with inherent viscosities ranging from 0.42 to 0.62 dL/g. All the above polymers were fully characterized by elemental analysis, viscosity measurements, solubility test, FTIR spectroscopy, differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA and DTG). 1,3-Bis [4,4'-bis(trimellitimidoyl chloride) phenyl]-2-propenone 7 was synthesized by a four-step reaction. Initially, 4-nitro benzaldehyde 1 was reacted with 4-nitro acetophenone 2 in acetic anhydride to form 1,3-bis(4-nitro phenyl)-2-propenone 3. The dinitro 3 was then reduced to the diamine 4 using sodium sulfide. A condensation reaction of one equimolar of diamine 4with two equimolars of trimellitic anhydride 5 in a mixture of acetic acid and pyridine (3:2) led to the formation of 1,3-bis[4,4'-bis(trimellitimido) phenyl]-2-propenone 6. Finally the diacid 6 was converted to 1,3-bis[4,4'-bis(trimellitimidoyl chloride) phenyl]-2-propenone 7 by a reaction with thionyl chloride.
Khalil Faghihi,Mohsen Hajibeygi,Meisam Shabanian 한국고분자학회 2010 Macromolecular Research Vol.18 No.5
A new-type of dicarboxylic acid 6 was synthesized from a reaction of 1,5-bis(4-aminophenyl)penta-1,4-dien-3-one 4 with trimellitic anhydride 5 in a glacial acetic acid/pyridine (Py) solution at refluxing temperature. Eight novel thermally stable poly(amide-imide)s (PAIs) 8a-h with good inherent viscosities were synthesized from a direct polycondensation reaction of N,N'-(1,5-bis(4-aminophenyl)penta-1,4-dien-3-one)bistrimellitimide 6 with several aromatic diamines 7a-h through direct polycondensation using the N-methyl-2-pyrrolidone (NMP)/pyridine (py)/triphenyl phosphite (TPP) system as a condensation agent. All the above polymers were fully characterized by 1H NMR, FTIR, elemental analysis, inherent viscosity, solubility tests, UV-vis spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and the derivative of thermaogravimetric (DTG). The resulting poly(amide-imide)s (PAIs) 8a-h showed good inherent viscosities (0.41-0.70 dL/g), good thermal stability and solubility.