• Title/Summary/Keyword: poly(amide imide)

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Using Microwave Irradiation to Prepare New Poly(amide-imide)s Containing Tetrahydropyrimidinone, Tetrahydro-2-thioxopyrimidine, and Trimellitic Rings in Their Main Chains: Synthesis and Characterization

  • Faghihi Khalil;Hagibeygi Mohsen
    • Macromolecular Research
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    • v.13 no.1
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    • pp.14-18
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    • 2005
  • 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.

Polyaramide-Imide from N-Phenylphthalimide-Containing Diamine and Dicarboxylic Acid I. Synthesis and Thermal Properties (N-Phenylphthalimide를 포함하는 디아민과 디카르복시산으로 제조된 폴리아라미드-이미드 I. 제조와 열적 성질)

  • Kil, Deog-Soo;Bae, Jang-Soon;Choi, Sung-Jae;Gong, Myoung-Seon
    • Applied Chemistry for Engineering
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    • v.10 no.1
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    • pp.138-142
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    • 1999
  • Imide-containing diamine and dicarboxylic acid monomers, N-(4-aminophenyl)-4-aminophthalimide(APAP), N-(4-carboxyphenyl)-4-carboxyphthalimide(CPCP), N,N'-oxydiphenylenebis(4-aminophthalimide)(ODPAP) and N,N'-oxydiphenylenebis(4-carboxyphthalimide)(ODPCP) were prepared. Poly(amide-imide)s were prepared by condensation reaction of the diamine and the dicarboxylic acid monomers. Poly(amide-imide)s were also prepared from the diamine monomers and aromatic acid chlorodes such as terephthaloyl chloride and isophthaloyl chloride. The polymers possess inherent viscosity of 0.18~0.67 dL/g and brittle films were cast from NMP/LiCl solution. The poly(amide-imide)s are easily soluble in NMP/LiCl and also partially soluble in polar aprotic solvents such as DMF, DMSO, NMP and DMAc even at $80^{\circ}C$. DSC traces of polymers showed no glass transition temperature and melting temperature, and TGA traces showed a 10% weight loss at $500^{\circ}C$.

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Microwave Assisted Rapid Synthesis of Novel Optically Active Poly(amide-imide)s Based on N-Trimellitylimido-L-Leucine Diacid Chloride and Hydantoin Derivatives

  • Faghihi, Khalil
    • Macromolecular Research
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    • v.12 no.3
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    • pp.258-262
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    • 2004
  • 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.

Syntheses of New Film-Forming Aromatic Poly(amide-imide)s Containing Isoindoloquinazolinedione Unit in the Backbone: Poly(biphenylphthalicdianhydride-oxydianiline-4,4-diamino-3-carbamoyl-benzanilide) (Poly(BPDA-ODA-DACB))

  • Kang, Seog-Joo;Hong, Sung-Il;Park, Chong-Rae;Oh, Tae-Jin
    • Fibers and Polymers
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    • v.2 no.2
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    • pp.92-97
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    • 2001
  • New film forming aromatic poly(amide-imide)s containing isoindoloquinazolinedione (IQ) unit in the backbone chain (polymer XIV) have been successfully synthesized by preparing prepolymers of poly(amic acid-carbonamide). followed by subsequent thermal cyclization of the prepolymers. 4,4-Diamino-3-carbamoylbenzanilide (DACB) V has been synthesized by reduction of 3-carbamoyl-4-amino-4-nitrobenzanilide IV. The prepolymers of poly(amic-acid-carbonamide) (polymers VII and VIII) which exhibit viscosities ranging from 1.4 to 1.7 dl/g have been prepared by a condensation polymerization of monomers such as BPDA, ODA, and DACB. Polymer XIV has been obtained by thermal cyclization of the polymers VII and VIII. During the thermal cyclization reaction, imide ring structure was first introduced and then transformed to the structure of IQ unit. The thermal degradation rate of the resultant polymers were influenced by the cleavage of amide bond but the final char yield was comparable to that of poly(BPDA-ODA).

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Noble Aromatic Poly(amide-imide)s Derived from 1,2-Bis(4-trimellitimidophenoxy)benzene (1,2-Bis(4-trimellitimidophenoxy)benzene으로 부터 유도된 신규 방향족 폴리아미드이미드)

  • Jeong, Hwa-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.27 no.2
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    • pp.129-136
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    • 2010
  • A series of noble poly(amide-imide)s and copoly(amide-imide)s bearing 1,2-bis(4-phenoxy)benzene units were synthesized by the direct polycondensation of 1,2-bis(4-trimellitimidophenoxy)benzene[1,2-PTPB] with a combination of commercially available aromatic diamines and diacids such as m-phenylene diamine, p-phenylene diamine(PPD), isophthalic acid and terephthalic acid(TA) in N-methyl-2-pyrrolidone(NMP) using triphenyl phosphite and pyridine as a condensing agent in the presence of dehydrating agent ($CaCl_2$). The resulting polymers had inherent viscosities in the range of 0.37~0.78 dL/g and most of them were soluble m common organic solvents including NMP, dimethylacetamide, dimethylsulfoxide, dimethylformamide, and m-cresol. Wide-angle X-ray diffractograms revealed that the copoly(amide-imide) derived from PPD with mixed acids of 1,2-BTPB and TA, showed crystalline nature, whereas all of the other polymers were found to be amorphous. The glass transition temperatures of the polymers occurred over the temperature range of $270{\sim}323^{\circ}C$ in their differential scanning calorimetry curves and their 10% weight loss temperature, determined by thermogravimetric analysis in air and nitrogen atmosphere, were in the range $465{\sim}535^{\circ}C$, $500{\sim}550^{\circ}C$, respectively, indicating their good thermal stability.

A Study on Chemical Cyclodehydration of Aromatic Poly(ether-amide-amic acid)s (방향족 폴리(에테르-아미드-아미드산) 중합체의 화학적 탈수 고리화 반응)

  • Ahn, Young Moo
    • Textile Coloration and Finishing
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    • v.7 no.4
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    • pp.39-44
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    • 1995
  • A study has been made about some correlations in the chemical cyclization of precursors, poly(ether-amide-amic acid)s by treating in solution a mixture of acetic anhydride and pyridine in the presence of 4,4-dimethyl formamide, with the poly(ether-amic acid)s being respectively reacted between trimellitic anhydride chloride and 3 kinds of diamines, i.e., 4,4'-bis(m-aminophenoxy) benzophenone, 2,2'-bis[4-(m-aminophenoxy) phenyl] propane and 4,4'-bis(m-aminophenoxy) diphenyl sulfone. The cyclization of imide ring in the poly(ether-amide-amic acid)s may be regarded as an intramolecular acylation of amide group by o-carboxyl group. As a result of this reseach, the effects on the conversion to poly(ether-amide-imide)s have been found by changing the ratio of cosolvents in the cyclization mixture.

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Synthesis and Characterization of Copoly(amide-imide) Derivatives and Ultrafiltration Membrane Performances II - Permeation Properties of Copoly(amide-imide)s Ultrafiltration Membranes -

  • Jeon, Jong- young;Kim, Jong-hp
    • Korean Membrane Journal
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    • v.3 no.1
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    • pp.24-31
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    • 2001
  • Ultrafiltration membranes base on copoly(amide-imide) derivatives were prepared by the phase inversion method and the factors determining the permeation characteristics of membrane were investigated. The permeation behavior was observed by the relative ratio of permeate flux (J$\_$t/)/pure water flux (J$\_$o/). The characteristics through membrane were measured using aqueous solution of poly(ethyleneglycol) (MW 2.0$\times$10$\^$4/) over a temperature range of 10∼90$\^{C}$. With increasing the operating temperature, the relative ratio of flux became high. All the membranes had good chemical stability. Copoly(amide-imide) membranes having various Permeation properties could be obtained. Further, it was proved that the membrane performances could be determined from the preparation conditions as well as various operating conditions.

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Synthesis of Poly Imide/α'ω'-di Poly Acrylamide (3-Mercaptopropyl) Trimethoxysilane Terminated Copolymer (양 말단에 MPTMS-아크릴아미드로 치환된 폴리이미드의 합성)

  • Min, Jun Ho;Park, Chan Young;Min, Seong Kee
    • Korean Journal of Materials Research
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    • v.26 no.9
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    • pp.478-485
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    • 2016
  • An amide group was introduced to restrain the cohesion of silica nano-particles and copolymerized with polyamic acid. Amide block copolymers were prepared using silica and (3-mercaptopropyl) trimethoxysilane (MPTMS) with a siloxane group, using 2, 6-Lutidine as a catalyst. Amide block polymers and copolymers were synthesized via ATRP after brominating pyromellitic dianhydride (PMDA) and polyamic acid of methylene diphenyl diamine (MDA) using ${\alpha}$-bromo isobutyryl bromide. Characteristic peaks of copolymer with amide and imide groups and patterns of amorphous polymers were studied using FT-IR and XRD analyses; an analysis of the surface characteristic groups was conducted via XPS. Changes in the thermal properties were examined through DSC and TGA; solubility for solvents was also studied.

Preparation and Characterization of Poly(amide imide)-based Carbon Nanofibers/Epoxy Nanocomposites

  • Seo, Min-Kang;Choi, Kyeong-Eun;Park, Sang-Hee;Hong, Young-Taik;Park, Soo-Jin
    • Carbon letters
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    • v.10 no.4
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    • pp.329-334
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    • 2009
  • In this work, the effect of carbon nanofibers (CNFs) addition on physicochemical characteristics of CNFs-reinforced epoxy matrix nanocomposites was studied. Poly(amide imide) solutions in dimethylformamide were electrospun into webs consisting of $250{\pm}50$ nm fibers which were used to produce CNFs through stabilization and carbonization processes. As a result, the CNFs with average diameter of $200{\pm}20$ nm were obtained after carbonization process. The nanocomposites with CNFs showed an improvement of thermal stability parameters and fracture toughness factors, compared to those of the specimen without CNFs, which could be probably attributed to the higher specific surface area and larger aspect ratio of CNFs, resulting in improving the mechanical interlocking in the nanocomposites. Also, the applied external loading can effectively transfer to CNFs because strong interactions are resulted between the epoxy matrix and the CNFs.

Optically Active and Organosoluble Poly(amide-imide)s Derived from N,N'-(Pyromellitoyl)bis-L-histidine and Various Diamines: Synthesis and Characterization

  • Faghihi, Khalil;Shabanian, Meisam;Hajibeygi, Mohsen
    • Macromolecular Research
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    • v.17 no.11
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    • pp.912-918
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    • 2009
  • 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.