Low dielectric thermoset. IV. Synthesis and properties of a dipentene‐containing cyanate ester and its copolymerization with bisphenol A dicyanate ester

Lin, Ching Hsuan; Hsiao, C. N.; Li, Chun Hung; Wang, Chun Shan

doi:10.1002/pola.20226

Cited by 42 publications

(28 citation statements)

References 13 publications

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“…The char yield (measured at 600 °C) was 31 %. This value, although relatively low for cyanate ester thermosets, is not surprising given the extra mass of thermally labile moieties, which include the methoxy and aliphatic bridging groups 20. A simple calculation based only on the number of aromatic carbon atoms with the assumption that the cyanurate rings decompose completely to cyanuric acid gives a theoretical char yield of only 41 %.…”

Section: Resultsmentioning

confidence: 97%

A High‐Performance Renewable Thermosetting Resin Derived from Eugenol

et al. 2014

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A renewable bisphenol, 4,4'-(butane-1,4-diyl)bis(2-methoxyphenol), was synthesized on a preparative scale by a solvent-free, Ru-catalyzed olefin metathesis coupling reaction of eugenol followed by hydrogenation. After purification, the bisphenol was converted to a new bis(cyanate) ester by standard techniques. The bisphenol and cyanate ester were characterized rigorously by NMR spectroscopy and single-crystal X-ray diffraction studies. After complete cure, the cyanate ester exhibited thermal stability in excess of 350 °C and a glass transition temperature (Tg ) of 186 °C. As a result of the four-carbon chain between the aromatic rings, the thermoset displayed a water uptake of only 1.8% after a four day immersion in 85 °C water. The wet Tg of the material (167 °C) was only 19 °C lower than the dry Tg , and the material showed no significant degradation as a result of the water treatment. These results suggest that this resin is well suited for maritime environments and provide further evidence that full-performance resins can be generated from sustainable feedstocks.

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Section: Resultsmentioning

confidence: 97%

A High‐Performance Renewable Thermosetting Resin Derived from Eugenol

et al. 2014

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“…Similar tendencies were also observed for 2,6-dimethyl phenol dipentane dicyanate ester and their cocyanate esters with BADCY. 20 The reasons for this phenomenon are still unknown, and further research is necessary to understand it. Figure 9 shows the T gcomposition plot of cocyanate ester; T g increased with the content of BADCY, and a positive deviation from the Fox equation can be observed.…”

Section: Dma Measurementsmentioning

confidence: 97%

Dielectric behavior and properties of a cyanate ester containing dicyclopentadiene. I

Hwang

Wang

2005

J of Applied Polymer Sci

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2,6-Dimethyl phenol dicyclopentadiene dicyanate ester (DCPDCY) was synthesized through the reaction of 2,6-dimethyl phenol dicyclopentadiene novolac and cyanogen bromide. The proposed structure was confirmed by Fourier transform infrared, mass spectrometry, NMR spectrometry, and elemental analysis. DCPDCY was then cured by itself or cured with bisphenol A dicyanate ester (BADCY) to form triazine structures. The thermal properties of the cured DCPDCY resins were studied with differential scanning calorimetry, dynamic mechanical analysis (DMA), dielectric analysis, and thermogravimetric analysis; these data were compared with those of BADCY. The cured DCP-DCY resins exhibited a lower dielectric constant (2.58 at 1 MHz), a lower dissipation factor (20.2 mU at 1 MHz), less thermal stability (the 5% degradation temperature and char yield were 430°C and 32.1%, respectively), a lower glasstransition temperature (266°C by thermomechanical analysis and 271°C by DMA), a lower coefficient of thermal expansion (22.5 ppm before the glass-transition temperature and 124.9 ppm after the glass-transition temperature), and less moisture absorption (0.88% at 48 h) than BADCY, but they showed higher moduli (6.28 GPa at 150°C and 5.35 GPa at 150°C) than the bisphenol A system. The properties of the cured cocyanate esters (DCPDCY and BADCY) lay between those of cured BADCY and DCPDCY, except for the moduli. The moduli of some cocyanate esters were even higher than those of cured BADCY and DCPDCY. A positive deviation from the Fox equation was observed for cocyanate esters.

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“…For example, despite the excellent dielectric properties of epoxy, silver filled epoxies with good electrical conductivity are widely available are considered promising alternatives for lead‐containing solder alloy in the electronics industry 3–8. Epoxy‐based materials are also widely used in a variety of applications, such as paints and coatings, adhesives, industrial tooling and composites, flip‐chip under fills,9–12 low dielectric‐constant components,13, 14 and semiconductor capsulation films in the electronics industry. Various types of curing agents, such as nitrogen containing agents (amines and polyamides), oxygen containing agents (anhydride), and sulfur containing agents (mercaptans), have been reacted with epoxy resins to provide cross‐linked adhesives.…”

Section: Introductionmentioning

confidence: 99%

Studies on the curing kinetics and thermal stability of diglycidyl ether of bisphenol‐A using mixture of novel, environment friendly sulphur containing amino acids and 4,4′‐diaminodiphenylsulfone

Darshan¹,

Malhotra²,

Narula³

2009

J of Applied Polymer Sci

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This article describes the curing behavior of diglycidyl ether of bisphenol-A using Cysteine (A)/ Methionine (B)/Cystine (C)/ mixture of 4,4 0 -diaminodiphenyl sulfone (DDS) and Cysteine/DDS and Methionine/DDS and Cystine in various molar ratios as curing agent. Differential scanning calorimetry was used to study the cure kinetics by recording the DSC scans at heating rates of 5, 10, 15, and 20 C/min. The peak exotherm temperature was found to be dependent on the heating rate, structure of the amino acids and on the DDS/amino acids molar ratio. A broad exotherm was observed in the temperature range of 150-245 C (EA), 155-240 C (EB), and 190-250 C (EC). Curing of DGEBA with mixture of amino acids and 4, 4 0 -diaminodiphenyl sulfone (DDS) resulted in a decrease in characteristic curing temperatures. Activation energy of curing reaction is determined in accordance to Ozawa's method and was found to be dependent on the structure of the amino acids and on the ratio of 4,4 0 -diaminodiphenyl sulfone (DDS) to amino acid. Thermal stability of the isothermally cured resins was evaluated using dynamic thermogravimetry in nitrogen atmosphere. No significant change has been observed in the char yield of all the samples, but it was highest in the system cured using either Cystine alone (EC-1) or a mixture of DDS/Cystine (EC-2, EC-3, and EC-4).

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Low dielectric thermoset. IV. Synthesis and properties of a dipentene‐containing cyanate ester and its copolymerization with bisphenol A dicyanate ester

Cited by 42 publications

References 13 publications

A High‐Performance Renewable Thermosetting Resin Derived from Eugenol

A High‐Performance Renewable Thermosetting Resin Derived from Eugenol

Dielectric behavior and properties of a cyanate ester containing dicyclopentadiene. I

Studies on the curing kinetics and thermal stability of diglycidyl ether of bisphenol‐A using mixture of novel, environment friendly sulphur containing amino acids and 4,4′‐diaminodiphenylsulfone

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