Curing kinetics of diglycidyl ether of bisphenol‐A (<i>n</i> = 0) using an iron‐containing porphyrin as cross‐linking agent

Vázquez, Eva C.; Fraga, F.; Martínez-Ageitos, J. M.; Tato, José Vázquez

doi:10.1002/app.39659

Cited by 10 publications

(14 citation statements)

References 56 publications

(61 reference statements)

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“…This confirms that the appearance of the asymmetric shoulder in the thermograms of samples with excess epoxy is due to the etherification reaction (Figure 9a) [14]. The signals at 1610 and 1510 cm -1 , assigned to the C=C and C-C bonds of benzene rings of the resin, do not exhibit significant changes during the polymerization although they increase with the proportion of resin.…”

Section: Infrared Spectroscopysupporting

confidence: 79%

“…The resin was stored in a desiccator protected from light to prevent oxidation and carbonation while hemin was stored in the refrigerator at a temperature between 2-8°C. The optimum molar ratio 6:1 (BADGE, n = 0/hemin) have been used [14]. These compounds were carefully and homogeneously mixed at room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…Reasons for choosing the molar ratio 6:1 as optimal rate for this system have been given elsewhere [14]. Additionally, the glass transition temperature (T g ) is also a function of the reaction stoichiometry.…”

Section: Thermal Analysismentioning

confidence: 99%

“…In a previous paper [14] we have calculated the kinetic parameters using Kamal model. This model is used for describing the isothermal experiments, but the statistical criteria do not allow setting exact power exponents.…”

Section: Kinetic Studiesmentioning

confidence: 99%

“…Dicarboxylate ferrocene has also been used [13]. Macrocycles can be used as crosslinking agents for curing the BADGE, n = 0 epoxy resin, allowing for the introduction of a metal ion into the network structure, as we have recently demonstrated [14], hemin (a protoporphyrin IX containing the Fe(III) ion, and an additional chloride ligand) being used. As crosslinking agents, metallomacrocycles can offer the advantage of a complexed ion, while the organic functionalities of the macrocycle may be used for the curing process.…”

Section: Introductionmentioning

confidence: 99%

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Paramagnetic epoxy resin

Barreiro¹,

Fraga²,

Jover³

et al. 2017

Express Polym. Lett.

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Abstract. This work illustrates that macrocycles can be used as crosslinking agents for curing epoxy resins, provided that they have appropriate organic functionalities. As macrocycles can complex metal ions in their structure, this curing reaction allows for the introduction of that metal ion into the resin network. As a result, some characteristic physical properties of the metallomacrocycle could be transferred to the new material. The bisphenol A diglycidyl ether (BADGE, n = 0) and hemin (a protoporphyrin IX containing the Fe(III) ion, and an additional chloride ligand) have been chosen. The new material has been characterized by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), Fourier Transform Infrared (FT-IR), Nuclear Magnetic Resonance (NMR), Transmission Electron Microscopy (TEM), and magnetic susceptibility measurements). Fe(III) remains in the high-spin state during the curing process and, consequently, the final material exhibits the magnetic characteristics of hemin. The loss of the chlorine atom ligand during the cure of the resin allows that Fe(III) can act as Lewis acid, catalyzing the crosslinking reactions. At high BADGE n = 0/hemin ratios, the formation of ether and ester bonds occurs simultaneously during the process.

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Section: Infrared Spectroscopysupporting

confidence: 79%

Section: Methodsmentioning

confidence: 99%

Section: Thermal Analysismentioning

confidence: 99%

Section: Kinetic Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Paramagnetic epoxy resin

Barreiro¹,

Fraga²,

Jover³

et al. 2017

Express Polym. Lett.

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New curing agents for epoxy resins: protoporphyrins

Fraga

Barreiro

Jover

et al. 2017

Polymers for Advanced Techs

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xTwo similar macrocycles protoporphyrin IX and zinc protoporphyrin IX (ZPP) have been used as cross-linking agents for curing the epoxy resin of bisphenol A diglycidyl ether (BADGE, n = 0). The enthalpies and the activation energies of the esterification reaction of the 2 systems are very close to each other. However, the temperature of the minimum in the differential scanning calorimetry thermogram is 38°C lower for BADGE (n = 0)/ZPP, thus requiring a less energy expenditure for curing the system. By the contrary, the enthalpy and activation energies for the etherification reaction are lower and higher, respectively, for BADGE (n = 0)/ZPP suggesting that the zinc ion affects it, although the involved mechanism is unknown. KEYWORDSepoxy resin, protoporphyrin IX, zinc protoporphyrin IX, Zn ion

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Analysis of curing of diglycidyl ether of bisphenol A (BADGE n = 0) with 2‐adamantylethanamine

Fraga

Válcarcel

Soto

et al. 2020

Polymers for Advanced Techs

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The epoxy resin diglycidyl ether of Bisphenol A (BADGE n = 0) has been cured with a new synthesized hardener (2‐adamantylethanamine) and the crosslinking reaction was characterized by DSC. Values of 413.3 J/g and 95°C have been obtained for the enthalpy of the reaction and the glass transition temperature, respectively. The experimental results obey Kamal's model over all conversion range of temperatures (70°C‐100°C). The activation energies of the mechanisms involved in the curing reaction have been determined for both the autocatalytic and the n‐order mechanism, the values being 63.3 and 29.8 kJ/mol, respectively. The value for Tg is 23°C higher than the one for (BADGE n = 0)/amantadine, while the activation energy for the n‐order mechanism is around 13 kJ/mol lower. This is consistent with a higher steric effect of the adamantyl group in the second hardener since it will hinder the opening the oxirane ring by the nitrogen atom of the amino group. As the polymerization reaction progress, this effect will disappear as the distance adamantyl‐oxirane increase when new oxirane groups react with the hydroxyl groups (autocatalyzed reaction). Consequently, by selecting the appropriate cross‐linking agent, it is possible to simultaneously increase Tg while reducing theactivation energy, two effects which may be desirable for some industrial applications of the material.

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Curing kinetics of diglycidyl ether of bisphenol‐A (n = 0) using an iron‐containing porphyrin as cross‐linking agent

Cited by 10 publications

References 56 publications

Paramagnetic epoxy resin

Paramagnetic epoxy resin

New curing agents for epoxy resins: protoporphyrins

Analysis of curing of diglycidyl ether of bisphenol A (BADGE n = 0) with 2‐adamantylethanamine

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