Polyisophthalamides with pendent phthalimide groups

Diakoumakos, Constantinos D.; Mikroyannidis, John A.

doi:10.1016/0032-3861(94)90992-x

Cited by 39 publications

(20 citation statements)

References 9 publications

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“…A flask equipped with magnetic stirrer was charged with a solution of phenol (1.6940 g, 18.0 mmol) and triethylamine (1.8214 g, 18.0 mmol) in DMAc (10 mL). 3,5-Dinitrobenzoyl chloride (4.1500 g, 18.0 mmol) dissolved in DMAc (15 mL) was added dropwise to the stirred solution at 0°C under N2. The mixture was stirred in a stream of N2 at ambient temperature for ca.…”

Section: Reagents and Solventsmentioning

confidence: 99%

Synthesis and properties of polyterephthalamides with ester pendent groups

Spiliopoulos

Mikroyannidis

1996

J. Polym. Sci. A Polym. Chem.

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3,5‐Dinitrobenzoyl chloride reacted with various alcohols such as phenol, biphenyl‐4‐ol, 1‐naphthol, or diphenylmethanol to afford the 3,5‐dinitrobenzoic acid ester derivatives which were catalytically hydrogenated to the corresponding diamines. The latter reacted with terephthaloyl dichloride to yield a new series of modified polyterephthalamides bearing pendent groups connected to the polymer backbone with ester linkages. The analogous unsubstituted polyterephthalamide were also prepared to compare the properties of the two series of aromatic polyamides. The polyamides were characterized by FT‐IR, 1H‐NMR, inherent viscosity, and water‐absorption measurements, x‐ray, DTA, TMA, TGA, and isothermal gravimetric analysis. The modified polyamides exhibited better solubility in certain organic solvents and higher hydrophilicity than the corresponding unmodified one. They were amorphous and softened at about 230°C. The glass transition temperatures ranged from 178 to 217°C. After an appropriate thermal treatment, crosslinking of modified polyamides was achieved and their thermal stability was slightly lower than that of parent unsubstituted polyamide. They were stable up to 354–370°C in N2 or air and afforded anaerobic char yields of 50–60% at 800°C. © 1996 John Wiley & Sons, Inc.

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Section: Reagents and Solventsmentioning

confidence: 99%

Synthesis and properties of polyterephthalamides with ester pendent groups

Spiliopoulos

Mikroyannidis

1996

J. Polym. Sci. A Polym. Chem.

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“…Model Diimide 4 A flask was charged with a solution of 3 (1.0000 g, 3.84 mmol) in DMF (10 mL). Phthalic anhydride (1.1374 g, 7.68 mmol) was added to the stirred solution a t 0°C.…”

Section: Preparation Of Model Compounds (Scheme 2)mentioning

confidence: 99%

Heat‐resistant polyimides and polyamides prepared from 2, 7‐diamino‐9‐dicyanomethylene‐fluorene

Diakoumakos

Mikroyannidis

1994

J of Applied Polymer Sci

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SYNOPSIS9-Fluorenone was nitrated with fuming nitric acid to yield 2,7-dinitro-fluorenone (1). It was condensed with malononitrile in the presence of glacial acetic acid and a catalytic amount of piperidine to afford 2,7-dinitro-9-dicyanomethylene-fluorene (2). It was catalytically hydrogenated to the corresponding diamine (3). The latter was used as starting material for the preparation of new polyimides and polyamides bearing dicyanomethylene units. In addition, a bismaleimide was synthesized from the reaction of 3 with maleic anhydride and subsequent cyclodehydration of the intermediate bismaleamic acid. The FT-IR spectra of polymers were in agreement with those of the synthesized model compounds. The polymers and bismaleimide yielded crosslinked resins upon curing at 300°C for 40 h in the presence of a catalytic amount of 4,4'-diaminodiphenylmethane. They were stable up to 355-430°C in N2 or air and afforded anaerobic char yield of 52%57% at 800°C. 0

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“…It is known that the solubility of polymers is often increased when flexible bonds such as [-O-, -SO 2 -, -CH 2 -, -C(CF 3 -) 2 ], bulky pendent groups (such as t-butyl and adamantyl), large pendent groups or polar constituents are incorporated into the polymer backbone due to the altering crystallinity and intermolecular interactions. [7][8][9][10][11][12][13][14] It has been recognized that the incorporation of aryl-ether linkages generally imparts an enhanced solubility, processability, and toughness of aromatic polyamides and polyimides as well as their copolymers without substantial diminution of thermal properties. [15][16][17][18][19][20] In this article, we describe synthesis and characterization a series of novel poly(ether-amide)s 7a-e containing methylene segments from the direct polycondensation reaction of 1,4-(4-carboxy phenoxy)butane 3 with 1,1-bis[4-aminophenoxy]methane 6a, 1,2-bis[4-aminophenoxy]ethane 6b, 1,3-bis [4-aminophenoxy]propane 6c, 1,4-bis [4-aminophenoxy] butane 6d and 4,4-diamino diphenylether 6e in a medium consisting of N-methyl-2-pyrrolidone, triphenyl phosphite, calcium chloride and pyridine.…”

Section: Introductionmentioning

confidence: 99%

Novel poly(ether-amide)s derived from 1,4-(4-carboxy phenoxy)butane and ethereal diamines: Synthesis and properties

Faghihi

Shabanian

2010

Macromol. Res.

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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 ( 1 H 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.

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Polyisophthalamides with pendent phthalimide groups

Cited by 39 publications

References 9 publications

Synthesis and properties of polyterephthalamides with ester pendent groups

Synthesis and properties of polyterephthalamides with ester pendent groups

Heat‐resistant polyimides and polyamides prepared from 2, 7‐diamino‐9‐dicyanomethylene‐fluorene

Novel poly(ether-amide)s derived from 1,4-(4-carboxy phenoxy)butane and ethereal diamines: Synthesis and properties

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