Studying the effect of the chloral group on the thermal and physical properties of aromatic cyanate esters

Hamerton, Ian; Howlin, Brendan J.; Mooring, Lyndsey; Stone, Corinne A.; Swan, Martin; Thompson, Scott M.

doi:10.1016/j.polymdegradstab.2014.07.022

Cited by 8 publications

(7 citation statements)

References 25 publications

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“…1 –4 This technology requires dielectric materials with low dielectric constant and dielectric loss because of the inverse relationship between the square root of the dielectric constant and the propagation delay of electronic signals. 5 In general, high-performance dielectric materials, such as cyanate ester (CE), 6 –10 bismaleimide–triazine (BT) resin, 11 –15 polytetrafluoroethylene resin, 16 and bismaleimide (BMI), 17,18 have been increasingly used in the field. Among these dielectric materials, BT resins display superior performance.…”

Section: Introductionmentioning

confidence: 99%

Thermally stabilized bismaleimide–triazine resin composites for 10-GHz level high-frequency application

Yang

Mao

et al. 2017

High Performance Polymers

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A hybrid cured resin with excellent dielectric and thermal properties was prepared with bismaleimide–triazine (BT) resin modified with 2,2′-diallylbisphenol A (DBA). The thermal and dielectric properties of the resin were investigated, and the effect of DBA concentration on the curing reaction was determined. Results indicated that DBA significantly influenced the curing reaction and the properties of the cured product. The modified BT resins exhibited outstanding thermal stability (initial decomposition temperature was over 400°C), although the stability was slightly lower than that of pure BT resins. The dielectric constant and dielectric loss of the cured resin decreased when DBA was introduced into the BT resins. Moreover, the fabricated resins showed dielectric constant of 2.91–3.07 and dielectric loss lower than 0.0057 under the testing high-frequency range of 1 GHz to 15 GHz. Overall, the BT resins modified by DBA display great potential to be applied in high frequency field.

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Section: Introductionmentioning

confidence: 99%

Thermally stabilized bismaleimide–triazine resin composites for 10-GHz level high-frequency application

Yang

Mao

et al. 2017

High Performance Polymers

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“…27 These results are in general agreement with other studies. 5, [16][17][18][19][20][28][29][30][31][32][33][34] The siliconcontaining analog of BADCy, bis(4-cyanatophenyl)dimethylsilane, or SiMCy, was synthesized in our laboratory according to a previously published procedure 27 that closely follows the original synthesis reported by Wright. 28,35 SiMCy exhibits a previously reported melting point of 338.2 ± 0.1 K, heat of fusion of 93 ± 1 J/g, and purity of 99.4 ± 0.1% after purification using chromatography.…”

Section: Methodsmentioning

confidence: 99%

Organic Crystal Engineering of Thermosetting Cyanate Ester Monomers: Influence of Structure on Melting Point

Guenthner

Ramirez²,

Ford³

et al. 2016

Crystal Growth & Design

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Key principles needed for the rational design of thermosetting monomer crystals, in order to control the melting point, have been elucidated using both theoretical and experimental investigations of cyanate esters. A determination of the thermodynamic properties associated with melting showed that the substitution of silicon for the central quaternary carbon in the di(cyanate ester), 2,2-bis(4-cyanatophenyl)propane, resulted in an increase in the entropy of melting along with a decrease in the enthalpy of melting, leading to a decrease in the melting temperature of 21.8 ± 0.2 K. In contrast, the analogous silicon substitution in the tri(cyanate ester), 1,1,1-tris(4-cyanatophenyl)ethane, resulted in no significant changes to the enthalpy and entropy of melting, accompanied by a small increase of 1.5 ± 0.3 K in the melting point. The crystal structure of 1,1,1-tris(4-cyanatophenyl)ethane was determined via single crystal X-ray diffraction, and the structures of these four di(cyanate esters) and tri(cyanate esters) were examined. Although both the empirical models of Lian and Yalkowsky, as well as Chickos and Acree, provided reasonable estimates of the entropy of melting of 2,2-bis(4-cyanatophenyl)propane, they successfully predicted only certain effects of silicon substitution, and did not capture the difference in behavior between the di(cyanate esters) and the tri(cyanate esters). Semi-empirical molecular modeling, however, helped to validate an explanation of the mechanism for the increase in the entropy of melting of the silicon-containing di(cyanate ester), while providing insight into the reason for the difference in behavior between the di(cyanate esters) and tri(cyanate esters). Taken together, the results assist in understanding how freedom of molecular motions in the liquid state may control the entropy of melting, and can be utilized to guide the development of compounds with optimal melting characteristics for high-performance applications.

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“…As investigated in the previous research, the limiting oxygen index (LOI) of CE (26%) is much higher than that of epoxy resin (22%), but it still failed in UL‐94 test. To improve the flame‐retardant property of CE, many researchers focused on either combining CE with high thermostable resin such as bismaleimide and benzoxazine or modifying CE with flame‐retardants such as halogen‐containing, phosphorus‐containing, sulfur‐containing, and silicon‐containing compounds …”

Section: Introductionmentioning

confidence: 99%

Study on properties of flame‐retardant cyanate esters modified with DOPO and triazine compounds

Chen

Wang

Huo

et al. 2018

Polymers for Advanced Techs

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Ternary flame-retardant modified cyanate ester blends (CEPG and CEPA) are formed by combining triazine compounds (TGIC or TAIC) and 9,10-dihydro-9-oxa-10phosphaphenanthrene-10-oxide with cyanate ester resin. The curing behaviors, thermal and mechanical properties, and the flame-retardant properties are investigated. The results show that the CEPG and CEPA blends result in lower curing temperatures and glass transition temperatures than those of neat CE. Both of CEPG and CEPA blends significantly improve the flame-retardant properties of CE resins, and UL-94V-0 rate is achieved for CEPG-1.0 and CEPA-0.5. The dielectric constant and loss of CEPA blends are lower than those of CEPG blend with the same phosphors content, and both of them are lower than those of neat CE. Therefore, the ternary flame-retardant modified cyanate ester blends provide 2 ways for composites of producing printed circuit board with high flame-retardant property and low dielectric constant and loss. KEYWORDS cone calorimeter, cyanate esters, dielectric constant and loss, phosphaphenanthrene, triazine compounds 1 | INTRODUCTION Cyanate ester (CE) exhibits high glass transition temperature, 1 low internal stress, 2 good adhesion, 3 low dielectric constant, 4 low toxicity, and high flame-retardant property, 5 due to the formed steady s-triazine ring by the self-curing of CE group. And owing to those advantages, CE offers several advantages over the commercial use high performance epoxy in aircraft field and electronic application. 6 However, as a thermoset resin, its flammability hinders its application which required high fire safety.As investigated in the previous research, the limiting oxygen index (LOI) of CE (26%) is much higher than that of epoxy resin (22%), but it still failed in UL-94 test. To improve the flame-retardant property of CE, many researchers focused on either combining CE with high thermostable resin such as bismaleimide and benzoxazine or modifying CE with flame-retardants such as halogen-containing, 7 phosphoruscontaining, 8,9 sulfur-containing, 10 and silicon-containing compounds. 11

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Studying the effect of the chloral group on the thermal and physical properties of aromatic cyanate esters

Cited by 8 publications

References 25 publications

Thermally stabilized bismaleimide–triazine resin composites for 10-GHz level high-frequency application

Thermally stabilized bismaleimide–triazine resin composites for 10-GHz level high-frequency application

Organic Crystal Engineering of Thermosetting Cyanate Ester Monomers: Influence of Structure on Melting Point

Study on properties of flame‐retardant cyanate esters modified with DOPO and triazine compounds

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