Structural features in epoxy networks from N-diglycidyl epoxies and amines: 1. Dominant intramolecular cyclization reaction in the reactions of N,N-diglycidylaniline with aniline and substituted anilines

Johncock, Peter; Tudgey, G. F.; Cûnliffe, A.V.; Morrell, R.K.

doi:10.1016/0032-3861(91)90021-a

Cited by 15 publications

(6 citation statements)

References 14 publications

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“…This was also supported by model reactions with diglycidylaniline/aniline, the peak patterns of which were similar and the cycles of which could be identified. This also compared favorably with data in the literature,6, 7 in which two peaks were also found that were identified as isomers of cycles.…”

Section: Resultssupporting

confidence: 81%

“…Fairly high amounts of cyclic products, around 25–30%, were reported with this model system 3, 4, 6. Another study with the same model reactions claimed a range of 15–45% that depended on structural factors 7…”

Section: Introductionmentioning

confidence: 62%

“…The residual epoxy content vanished at high curing temperatures (>180°C), and this indicated a full cure. Therefore, the oligomer distribution after network cleavage should be shifted to higher molecular weights comparable to those obtained from diglycidylaniline/aniline model reactions 3, 4, 6, 7, 17…”

Section: Resultsmentioning

confidence: 96%

“…This is most critical in cases in which two glycidyl units are located at the same atom; for example, a variety of reactions have been identified for tetraglycidyl diaminodiphenylmethane (Fig. 1) that lead to several cyclic structures 5–15…”

Section: Introductionmentioning

confidence: 99%

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Assessment of cyclization and network defects in glycidylamine‐based epoxy networks by selective degradation

Stütz¹,

Tesch²

2003

J of Applied Polymer Sci

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A special model system based on trimethylene glycol di(p-aminobenzoate) and its glycidyl derivative was evaluated to study the extent of cyclization in glycidylamine epoxies. The cured resins were degraded by alkaline hydrolysis, which left the cycles unaffected. The cycle concentration obtained by high-performance liquid chromatography was 15%. The oligomer distribution of the degradation products strongly indicated that up to 40% of the epoxy groups were lost to side reactions, and this resulted in a large number of structural defects in the network.

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Section: Resultssupporting

confidence: 81%

Section: Introductionmentioning

confidence: 62%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Assessment of cyclization and network defects in glycidylamine‐based epoxy networks by selective degradation

Stütz¹,

Tesch²

2003

J of Applied Polymer Sci

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“…The most significant difference of the reaction of TGDDM with amines from that of epoxides based on DGEBA is the strong tendency of TGDDM and its derivatives to cyclisation, in contrast to DGEBA where no cyclisation occurs. 14,15 In practice, many of the formulations incorporate catalysts to accelerate the thermal curing reaction. The two most commonly used are boron trifluoride monoethylamine, BF 3 : NH 2 C 2 H 5 , and boron trifluoride piperidine, BF 3 : NHC 5 H 10 , complexes.…”

Section: Introductionmentioning

confidence: 99%

Cure modeling and monitoring of epoxy/amine resin systems. I. Cure kinetics modeling

Karkanas

Partridge

2000

J. Appl. Polym. Sci.

146

130

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Polymers based on N,N‐diglycidylaniline. I. Investigations of the curing kinetics by dynamic differential scanning calorimetry measurements

Janeczek

Siwy

Schab‐Balcerzak

2009

J of Applied Polymer Sci

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N,N‐Diglycidylaniline was reacted with aniline (yielding polymer EP‐1) and the newly synthesized chromophore 4‐(phenylazo)aniline (yielding polymer EP‐2). The curing kinetics of these two epoxy resin systems was studied in dynamic experiments by means of differential scanning calorimetry. Kinetic parameters such as the activation energy and frequency factor were estimated with the Ozawa method [E(O) and A(O), respectively], the Kissinger method [E(K) and A(K), respectively], and the modified Avrami method [E(A) and A(A), respectively]. The activation energy and frequency factor of EP‐1 were much lower than those of EP‐2 estimated with the Ozawa, Kissinger, and Avrami methods. The activation energy and frequency factor for EP‐1 determined with the Ozawa method [E(O) = 55.8 kJ/mol, A(O) = 10 × 103 1/s] and the Avrami method [E(A) = 56.4 kJ/mol, A(A) = 9.2 × 103 1/s] were higher than those determined with the Kissinger method [E(K) = 51.0 kJ/mol, A(K) = 2 × 103 1/s]. In the case of EP‐2, the kinetic parameters calculated with the Ozawa model [E(O) = 140.4 kJ/mol, A(O) = 12.3 × 1013 1/s] and the Kissinger model [E(K) = 139.9 kJ/mol, A(K) = 10.9 × 1013 1/s] were higher than those calculated with the Avrami model [E(A) = 130.4 kJ/mol, A(A) = 7.9 × 1012 1/s]. The obtained polymers were characterized with Fourier transform infrared, 1H‐NMR, differential scanning calorimetry, and ultraviolet–visible spectroscopy. The polymers exhibited low glass‐transition temperatures in the range of 57–79°C and good solubility in common organic solvents. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009

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Structural features in epoxy networks from N-diglycidyl epoxies and amines: 1. Dominant intramolecular cyclization reaction in the reactions of N,N-diglycidylaniline with aniline and substituted anilines

Cited by 15 publications

References 14 publications

Assessment of cyclization and network defects in glycidylamine‐based epoxy networks by selective degradation

Assessment of cyclization and network defects in glycidylamine‐based epoxy networks by selective degradation

Cure modeling and monitoring of epoxy/amine resin systems. I. Cure kinetics modeling

Polymers based on N,N‐diglycidylaniline. I. Investigations of the curing kinetics by dynamic differential scanning calorimetry measurements

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