Synthesis and characterization of novel epoxy resin bearing naphthyl and limonene moieties, and its cured polymer

Xu, Kai; Chen, Mingcai; Zhang, Kui; Hu, Jiwen

doi:10.1016/j.polymer.2003.12.035

Cited by 95 publications

(69 citation statements)

References 31 publications

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“…They had lower dielectric constant (3.3) and water uptake (0.38%) than diglycidyl ether of bisphenol A (DGEBA) cured with the same curing agent. Xu et al 26 synthesized a series of novel epoxy resins bearing naphthyl and limonene moieties, which showed a remarkably higher T g (171 C), lower coefficient (36 ppm C…”

Section: -9mentioning

confidence: 99%

Preparation and characterization of novel naphthyl epoxy resin containing 4-fluorobenzoyl side chains for low-k dielectrics application

Jiang

Zhao

et al. 2017

RSC Adv.

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A new type of epoxy monomer 1,5-bis(4-fluorobenzoyl)-2,6-diglycidyl ether naphthalene (DGENF) was obtained through a three-step procedure involving Friedel-Crafts acylation, demethylation, and followed by nucleophilic reaction. The chemical structures were confirmed by 1 HNMR, 19 FNMR and FT-IR. After curing with methylhexahydrophthalic anhydride (MeHHPA), the properties of DGENF epoxy resin were measured and compared with three other kinds of commercial epoxy resins. As a result, DGENF exhibited excellent thermal stability, hydrophobic and dielectric properties. For example, DGENF had a higher glass transition temperature of 170 C than the other three commercial epoxy resins. DGENF showed a higher contact angle of 116 , which could satisfy the standard of hydrophobic materials. In addition, DGENF showed significantly lower dielectric constant (2.97 at 1 MHz) and dielectric loss (0.0188 at 1 MHz) than those of the other commercial epoxy resins because of the introduction of fluorine on the side chains, which improved the electronegativity of the epoxy resin and reduced the polarizability of molecules efficiently. Herein, we believe the novel naphthyl epoxy resin (DGENF) has demonstrated potential application in electronic industries.

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Section: -9mentioning

confidence: 99%

Preparation and characterization of novel naphthyl epoxy resin containing 4-fluorobenzoyl side chains for low-k dielectrics application

Jiang

Zhao

et al. 2017

RSC Adv.

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“…[15][16][17][18] In order to design and develop more novel epoxy resins with higher thermal and mechanical properties to meet the application need, the deeply understanding the effect of the molecular structure of materials on curing behavior, chemical and physical properties of epoxy resin was increasingly more important, because it can predict the end product properties of the new materials and provide a guide for the development process and speed up the development cycle. Varley et al utilized the relationship between the structure and properties as a tool, and formulated high-performance epoxyamine networks.…”

Section: -5mentioning

confidence: 99%

Effect of Structure of Bridging Group on Curing and Properties of Bisphenol-A Based Novolac Epoxy Resins

Pan

Zhang

et al. 2007

Polym J

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ABSTRACT:Three bisphenol-A based novolac epoxy resins with different bridging groups: methylene, methinephenyl and methine-naphthyl, respectively, between bisphenol-A phenyl rings were prepared to study the effect of structure of bridging group on curing and properties of the epoxy resins. The structures of the obtained epoxy resins were characterized using FT-IR and 1 H NMR spectra, the molecular weight and polydispersity index were determined using GPC. The effect of bridging groups on the curing kinetics, thermal mechanical properties, thermal stability, and moisture resistance of the synthesized epoxy resins cured with 4,4 0 -diaminodiphenyl sulphone (DDS) were investigated by dynamic differential scanning calorimetry, dynamic mechanical analysis, thermogravimetric analysis, X-ray diffraction and moisture absorption measurement. It was concluded that the methylene-bridged epoxy resin possessed the highest curing reaction reactivity toward DDS and the methine-naphthyl-bridged epoxy network possessed the highest storage modulus, glass transition temperatures, thermal stability, and moisture resistance. Epoxy resin has been utilized in many applications such as surface coatings, structural adhesives, printed circuit board, insulation materials for electronic devices, and advanced composites matrices due to its good thermal and dimensional stability, excellent chemical and corrosion resistance, and superior mechanical and electrical properties, in addition to ease of handling and processabilities. However, in hightech applications lower thermal expansion, higher toughness, better heat and moisture resistance were required.1 For this reason, much work has been continuously directed toward improving their thermal and physical properties by modifications of epoxy resins, in both backbone and pendant groups. 2-5Several approaches were adopted to enhance the heat resistance of epoxy resins with increasing crosslink density or introducing bulky structures such as biphenyl or naphthalene.6-8 The introduction of naphthalene moiety is expected to greatly improve the thermal property and moisture resistance owing to its excellent rigidity, facile packing of molecules and significant degree of hydrophobicity.9-14 Many studies reported that epoxy resin showed remarkably higher glass transition temperature (T g ), higher thermal stability, higher flexural modulus, better moisture resistance, lower coefficient of thermal expansion when stiff naphthalene was inserted or appended by chemical modification. [15][16][17][18] In order to design and develop more novel epoxy resins with higher thermal and mechanical properties to meet the application need, the deeply understanding the effect of the molecular structure of materials on curing behavior, chemical and physical properties of epoxy resin was increasingly more important, because it can predict the end product properties of the new materials and provide a guide for the development process and speed up the development cycle. Varley et al. utilized the relationship between the ...

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“…For example, epoxy resins possess excellent thermal stability, moisture resistance, chemical stability, superior electrical and mechanical properties and good adhesion to many substrates [1][2][3]. As well as known properties, such as, the superior mechanical and chemical properties of epoxy polymers are profited from the complicated curing processes, in which a low molecular weight oligomer is transformed into an infinite molecular weight polymer forming a three-dimensional network structure.…”

Section: Introductionmentioning

confidence: 99%

Curing kinetics, mechanism and chemorheological behavior of methanol etherified amino/novolac epoxy systems

Zhao¹,

Zhang²,

Sun³

et al. 2014

Express Polym. Lett.

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Abstract. The curing kinetics and mechanism of epoxy novolac resin (DEN) and modified epoxy novolac resin (MDEN) with methanol etherified amino resin were studied by means of differential scanning calorimetry (DSC), Fourier transforminfrared (FT-IR) spectroscopy and chemorheological analysis. Their kinetics parameters and models of the curing were examined utilizing isoconversional methods, Flynn-Wall-Ozawa and Friedman methods. For the DEN mixture, its average activation energy (E a ) was 71.05 kJ/mol and the autocatalytic model was established to describe the curing reaction. The MDEN mixture exhibited three dominant curing processes, termed as reaction 1, reaction 2 and reaction 3; and their E a were 70.05, 106.55 and 101.91 kJ/mol, respectively. Besides, E a of reaction 1 was similar to that of DEN mixture, while E a of reactions 2 and 3 corresponded to that of the etherification reaction between hydroxyl and epoxide group. Moreover, these three dominant reactions were n th order in nature. Furthermore, their curing mechanisms were proposed from the results of DSC and FTIR. The chemorheological behavior was also investigated to obtain better plastics products via optimizing the processing schedules.

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Synthesis and characterization of novel epoxy resin bearing naphthyl and limonene moieties, and its cured polymer

Cited by 95 publications

References 31 publications

Preparation and characterization of novel naphthyl epoxy resin containing 4-fluorobenzoyl side chains for low-k dielectrics application

Preparation and characterization of novel naphthyl epoxy resin containing 4-fluorobenzoyl side chains for low-k dielectrics application

Effect of Structure of Bridging Group on Curing and Properties of Bisphenol-A Based Novolac Epoxy Resins

Curing kinetics, mechanism and chemorheological behavior of methanol etherified amino/novolac epoxy systems

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