Effect of Particle Size of DABCO- and DBU- Intercalatedα-Zirconium Phosphate as Latent Thermal Catalysts inthe Reaction of Glycidyl Phenyl Ether（GPE） andHexahydro-4-Methylphthalic Anhydride（MHHPA）

Shimomura, Osamu; Sueto, Rena; Kusu, Hideki; Ueoka, Hiroki; Ohtaka, Atsushi; Nomura, Ryoji

doi:10.11618/adhesion.54.258

Cited by 5 publications

(6 citation statements)

References 15 publications

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“…The %conversion values for GPE with TBD for a 1 h reaction over the temperature range 60 to 120 • C are shown in Figure 1b, and it is clear that the polymerization reaction did not proceed under the specified conditions. performance as latent thermal initiators in the reaction of GPE with hexahydro-4-methylphthalic anhydride (MHHPA) [13][14][15][16]. However, it is important to develop a highly active latent initiating system to avoid the need for high-temperature curing.…”

Section: Resultsmentioning

confidence: 99%

“…We have previously reported that primary alkylamines intercalated with α-zirconium phosphate (α-ZrP) may serve as latent thermal initiators in the reaction of glycidyl phenyl ether (GPE) [11,12], and that the compounds 1,4-diazabicyclo [2,2,2] with hexahydro-4-methylphthalic anhydride (MHHPA) [13][14][15][16]. However, it is important to develop a highly active latent initiating system to avoid the need for high-temperature curing.…”

Section: Introductionmentioning

confidence: 99%

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Temperature-Dependent Enhancement Effects for TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) with 2-Methylimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Glycidyl Phenyl Ether

et al. 2019

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The catalytic effects of 1,1,3,3-Tetramethylguanidine (TMG), 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) in the reaction with glycidyl phenyl ether (GPE) at 40 °C were investigated. For the reaction, the %conversion of GPE was only 11%, carried out at 40 °C over 14 days in the presence of TBD.Additionally, there was little catalytic activity for the same reaction performed under typical storage conditions at 25 °C. The effect of TBD with 2-methylimidazole-intercalated α-zirconium phosphate (α-ZrP∙2MIm), as a latent thermal initiating system in the reaction with GPE, was then examined. The reaction did not proceed within 1 h at 80 °C. On increasing the temperature to 120 °C, the %conversion reached 75% for reaction at 1 h. Under typical storage conditions (7 days at 25 °C), the %conversion of GPE was only 7%. With addition of TBD to α-ZrP∙2MIm, reagent stability was maintained, and the polymerization reaction proceeded rapidly with the application of heat.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Temperature-Dependent Enhancement Effects for TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) with 2-Methylimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Glycidyl Phenyl Ether

et al. 2019

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“…The intercalation of DBU into the layers of α-Zr(HPO 4 ) 2 •H 2 O (α-ZrP) was carried out by slightly modifying a previously reported method [10]. Approximately 5.0 g of α-ZrP was added to 33 mL of a DBU 0.256 g (1.68 mmol) methanol solution.…”

Section: Preparation Of Dbu-intercalatedmentioning

confidence: 99%

“…Recently, we reported that DBU-intercalated α-zirconium phosphate (α-ZrP•DBU) served as a latent thermal catalyst in the reaction of epoxy resins. The α-ZrP•DBU catalyst can be obtained simply by mixing DBU and α-ZrP in methanol at ambient temperature [10]. The intercalated compound of α-ZrP•DBU is expected to possess different reactivity with organic compounds and organic salts.…”

Section: Introductionmentioning

confidence: 99%

DBU-Intercalated α-Zirconium Phosphates as Latent Thermal Catalysts in the Reaction of Hexamethylene Diisocyanate and Phenol

et al. 2021

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The catalytic activity of 1,8-diazabicyclo [5,4,0]undec-7-ene-intercalated α-zirconium phosphates (α-ZrP·DBU) as thermal latent catalysts in the reaction of hexamethylene diisocyanate (HDI) and phenol was investigated. α-ZrP intercalation compounds with varying amounts of DBU (α-ZrP·xDBU, where x = 0.58, 0.44, 0.22, and 0.10) were prepared. The reaction of HDI and phenol with α-ZrP·DBU was carried out at varying temperatures for 30 min periods. The α-ZrP·DBU showed high catalytic activity in the reaction of HDI-phenol under heating conditions. The α-ZrP·DBU extended the pot lifetimes at 25 °C.

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“…Latent thermal initiators must retain high activity under targeted temperatures while maintaining stability under storage conditions [1][2][3][4][5][6][7][8][9][10]. We have previously reported that primary alkylamines intercalated with α-zirconium phosphate (α-ZrP) can serve as latent thermal initiators in the reaction of glycidyl phenyl ether (GPE) [11,12] and that intercalation compounds of 1,4-diazabicyclo [2,2,2]octane (DABCO), 1,8-diazabicyclo [5,4,0]undec-7-ene (DBU), imidazole (Im), 2-methylimidazole (2MIm), and 2-ethyl-4-methylimidazole (2E4MIm) with α-ZrP (α-ZrP•DABCO, α-ZrP•DBU, α-ZrP•Im, α-ZrP•2MIm, and α-ZrP•2E4MIm, respectively) show good performance as latent thermal initiators in the reaction of GPE with hexahydro-4-methylphthalic anhydride (MHHPA) [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Release Behavior of Benzimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Epoxy Resin

et al. 2019

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The intercalation compound of benzimidazole with α-zirconium phosphate (α-ZrP) was evaluated as a latent thermal initiator in the reaction of glycidyl phenyl ether (GPE) and hexahydro-4-methylphthalic anhydride (MHHPA). No reaction occurred at 60 °C after 1 h. Upon increasing the temperature to 140 °C, the conversion reached 97% after 1 h. The deintercalation ratio of Bim from the intercalation compound of benzimidazole with α-zirconium phosphate (α-ZrP·Bim) was measured in the reaction of the GPE-MHHPA system. The deintercalation ratio increased upon increasing the temperature, reaching 97% at 120 °C after 1 h. The storage stability at 25 °C and 40 °C in the reaction of GPE-MHHPA was tested and was found to be maintained for 14 days at 25 °C. The intercalation compound of α-ZrP·Bim can effectively serve as a latent thermal initiator in the reaction of GPE-MHHPA.

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Effect of Particle Size of DABCO- and DBU- Intercalatedα-Zirconium Phosphate as Latent Thermal Catalysts inthe Reaction of Glycidyl Phenyl Ether（GPE） andHexahydro-4-Methylphthalic Anhydride（MHHPA）

Cited by 5 publications

References 15 publications

Temperature-Dependent Enhancement Effects for TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) with 2-Methylimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Glycidyl Phenyl Ether

Temperature-Dependent Enhancement Effects for TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) with 2-Methylimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Glycidyl Phenyl Ether

DBU-Intercalated α-Zirconium Phosphates as Latent Thermal Catalysts in the Reaction of Hexamethylene Diisocyanate and Phenol

Release Behavior of Benzimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Epoxy Resin

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