Imidazole substituted benzothiadiazole derivatives as latent curing agent for epoxy thermosetting resin

Zhang, Jie; Guo, Zongwei; Ma, Jinpeng; Song, Lingxiao; Yang, Guorui; Ao, Yuhui; Shang, Lei; Li, Ming

doi:10.1002/app.52263

Cited by 6 publications

(4 citation statements)

References 42 publications

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“…Furthermore, the thermal stability of the PI films tended to decrease gradually with the addition of quinoline and its derivatives, and PI-QL-7.5% showed a considerably lower T HRI value of only 220 °C, which was more than 30 °C lower compared to PI-200. From the reported studies, [15,46,47] it is clear that low-temperature curable accelerators would result in a significant reduction in the thermal stability of PI due to the instability of small molecular compounds blended at high temperatures. However, the thermal stability of PI films with 4QL and NQL was significantly improved compared to PI-QL.…”

Section: Thermal Propertiesmentioning

confidence: 99%

Exploring the Impact of Blend and Graft of Quinoline Derivative in Low‐Temperature Curable Polyimides

Huang,

Lv,

Zhang

et al. 2023

Macromol. Rapid Commun.

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The utilization of accelerators has been a common approach to prepare low‐temperature curable polyimide (PI). However, the accelerators have gradually fallen out of favor because of their excessive dosages and negative effect on the properties of PI. In this work, a new strategy of introducing accelerators by grafting to eliminate these disadvantages is presented. A novel quinoline derivative named NQL was designed for this purpose, and an ultra‐low dosage of only 2.5 mol% was sufficient to prepare low‐temperature curable PI. The favorable low‐temperature curing effect of NQL was attributed to its strong alkalinity (pKa = 18.47) and electron‐donating ability (HOMO = ‐6.22 eV). At a curing temperature of 200 °C, the PI with 2.5 mol% NQL showed outstanding properties (Young's modulus of 5.73 GPa, elongation of 37.3%, tensile strength of 237 MPa and coefficient of thermal expansion of 16 ppm/K). In particular, NQL could even lower the curing temperature to 180 °C and the ultra‐low temperature curable PI film still retained excellent properties. These results demonstrate that introducing low‐temperature curable accelerators by partial grafting instead of blending is a promising way to furnish low‐temperature curable PI, and provide insights into the preparation of polyimide with high performance in advanced packaging.This article is protected by copyright. All rights reserved

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Section: Thermal Propertiesmentioning

confidence: 99%

Exploring the Impact of Blend and Graft of Quinoline Derivative in Low‐Temperature Curable Polyimides

Huang,

Lv,

Zhang

et al. 2023

Macromol. Rapid Commun.

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“…Under the heat flow of 200 kW/m 2 for 320 s, the back-face temperature of the coating reached only 160 • C, and its surface after ablation was smooth. Existing research has focused on modifying epoxy resins by introducing polymers with high thermal stability to increase the char yield of the matrix [15][16][17]. This method has a significant effect on improving the carbon residue rate of epoxy resin, but the modification process is complicated and expensive, which is not suitable for large-scale civil applications.…”

Section: Introductionmentioning

confidence: 99%

Thermal Stability, Mechanical Properties and Ceramization Mechanism of Epoxy Resin/Kaolin/Quartz Fiber Ceramifiable Composites

Xue

Qin

et al. 2022

Polymers

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The application of epoxy resins in high temperature and thermal protection fields is limited due to their low decomposition temperature and low carbon residual rate. In this paper, epoxy resin (EP)/quartz fiber (QF) ceramifiable composites were prepared using a prepreg-molding process. The thermal stability, phase change and mechanical properties after high-temperature static ablation and ceramization mechanism of EP/QF ceramifiable composites were investigated. The addition of glass frits and kaolinite ceramic filler dramatically increases the thermal stability of the composites, according to thermogravimetric (TG) studies. The composite has a maximum residual weight of 61.08%. The X-ray diffraction (XRD) results show that the mullite ceramic phase is generated, and a strong quartz diffraction peak appears at 1000 °C. The scanning electron microscope (SEM) and element distribution analyses reveal that the ceramic phase generated inside the material, when the temperature reaches 1000 °C, effectively fills the voids in composites. The composites have a bending strength of 175.37 MPa at room temperature and retain a maximum bending strength of 12.89 MPa after 1000 °C treatment.

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“…The curing mechanism relies on the reaction of an epoxy group with a curing agent. Thus, the essence of slowing the curing rate is to largely reduce the activity of the curing agent, which is also one of the approaches used to produce single-component epoxy resin systems with longer shelf lives. , The introduction of an electronic effect and/or steric hindrance effect is an effective way to lower the reactivity of the curing agent . On the basis of this strategy, Chang et al prepared three low-activity benzoxazines, based on 1,4-phenylenediamine, 4,4′-diaminodiphenyl ether, and 4,4′-diaminodiphenylmethane (DDM) as latent heat curing agents.…”

Section: Introductionmentioning

confidence: 99%

Slow Curing of Epoxy Resin Underwater at High Temperatures

Zhu

Yin

et al. 2022

Ind. Eng. Chem. Res.

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Epoxy resins have been widely applied in various industrial fields, because of their high performances. However, previous studies mainly focused on low and medium temperatures; thus, curing behavior at high temperatures was less documented, which largely limits the deep understanding of epoxy resin formation and their applications in wider conditions. In this work, a novel curing agent, 4,4′-((methylenebis(4,1-phenylene))bis(azanediyl))bis(4-(furan-2-yl)butan-2-one) (AFPA), has been designed and synthesized via a one-pot method. The gelation time of epoxy system with AFPA underwater at 120 and 150 °C reaches 20 and 8 h, respectively. The activation energy of the system is calculated to be as high as 33.88 kJ mol–1, which accounts for the very long gelation time. Differential scanning calorimetry and thermogravimetric analysis results have shown that the glass-transition temperature of the epoxy resin is 123 °C, and the 5 wt % mass-loss temperature is 233 °C. Mechanical property tests have shown that the cured epoxy resin has good compressive strength, reaching 122 MPa at 30 °C and 41 MPa, even at 120 °C. A plugging experiment is designed and performed, and the results reveal that such epoxy system can easily pass through simulated formation rock fractures and cure in the presence of water at 120 °C to plug the fractures. We believe the findings in this work could provide an alternative way to develop systems with long curing times. Given the very long gelation time at high temperatures underwater and the good mechanical properties, such epoxy resin may find applications in water shut-off in the upstream of oil and gas industry, where water management underground is highly desired.

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Imidazole substituted benzothiadiazole derivatives as latent curing agent for epoxy thermosetting resin

Cited by 6 publications

References 42 publications

Exploring the Impact of Blend and Graft of Quinoline Derivative in Low‐Temperature Curable Polyimides

Exploring the Impact of Blend and Graft of Quinoline Derivative in Low‐Temperature Curable Polyimides

Thermal Stability, Mechanical Properties and Ceramization Mechanism of Epoxy Resin/Kaolin/Quartz Fiber Ceramifiable Composites

Slow Curing of Epoxy Resin Underwater at High Temperatures

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