Preparation of phosphinated bisphenol from acid-fragmentation of 1,1,1-tris(4-hydroxyphenyl)ethane and its application in high-performance cyanate esters

Lin, Jenshan; Tian, Tian; Dai, Ming

doi:10.1109/impact.2011.6117277

Cited by 3 publications

(4 citation statements)

References 19 publications

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“…It is known that the curing mechanism of CE is the cyclotrimerization of −OCN groups (Figure a) . This also exists in the DPDP/CE system; besides, there are additional chain extensions through forming iminocarbonate from the reaction between hydroxyl groups in DPDP and triazine rings (Figure b) .…”

Section: Resultsmentioning

confidence: 96%

Flame Retarding Cyanate Ester Resin with Low Curing Temperature, High Thermal Resistance, Outstanding Dielectric Property, and Low Water Absorption for High Frequency and High Speed Printed Circuit Broads

Chen

Liang

et al. 2015

Ind. Eng. Chem. Res.

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High-end electric products require high frequency and high speed printed circuit broads (HFS-PCBs), while high performance resin is the key for fabricating HFS-PCBs. A new resin system (DPDP/CE) was developed by copolymerizing 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DPDP) and 2,2′-bis(4-cyanatophenyl) propane (CE). Compared with CE resin postcured at 250 °C for 4 h, the DPDP/CE system that was only postcured at 220 °C for 2 h has outstanding flame retardancy, greatly reduced water absorption, low dielectric loss, and high thermal resistance. For DPDP1.4/ CE resin with 1.4 wt % phosphorus content, its dielectric constant and loss at 1 GHz are 2.71 and 0.005, respectively, and hardly change after staying in boiling water for 100 h. Different from UL-94 V-2 rating of CE resin, the flame retardancy of DPDP1.4/ CE resin is desirable UL-94 V-0 rating, resulting from both gas-phase and condensed-phase mechanisms. These attractive features suggest that the DPDP/CE system is suitable to fabricate HFS-PCBs for high-performance electric products.

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Section: Resultsmentioning

confidence: 96%

Flame Retarding Cyanate Ester Resin with Low Curing Temperature, High Thermal Resistance, Outstanding Dielectric Property, and Low Water Absorption for High Frequency and High Speed Printed Circuit Broads

Chen

Liang

et al. 2015

Ind. Eng. Chem. Res.

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“…A one pot-synthesis leading to phosphinated bisphenols by addition of 9,10-dihydro-9-oxa-10phosphaphenanthrene-10-oxide (DOPO) to either 1,1,1-tris(4-hydroxyphenyl)ethane or diaminophenylmethane-and diaminophenylether-based benzoxazines with subsequent conversion of the bisphenols to the corresponding dicyanate derivatives has been described [91,92]. The structures of the obtained cyanate ester monomers are depicted in Figure 11.12.…”

Section: Monomers Conferring Flame Retardancementioning

confidence: 99%

“…12 Chemical structures of the DOPO modified cyanester monomers used by Chang et al[92] (structures a and b) and Lin et al[91] (structure c).OCN NCOFigure 11.13 Chemical structure of 4,4 0 -bis (4-cyanatobenzyl) biphenyl (BBPCy)[12].…”

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confidence: 99%

Cyanate Esters

Kandelbauer

2014

Handbook of Thermoset Plastics

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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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Preparation of phosphinated bisphenol from acid-fragmentation of 1,1,1-tris(4-hydroxyphenyl)ethane and its application in high-performance cyanate esters

Cited by 3 publications

References 19 publications

Flame Retarding Cyanate Ester Resin with Low Curing Temperature, High Thermal Resistance, Outstanding Dielectric Property, and Low Water Absorption for High Frequency and High Speed Printed Circuit Broads

Flame Retarding Cyanate Ester Resin with Low Curing Temperature, High Thermal Resistance, Outstanding Dielectric Property, and Low Water Absorption for High Frequency and High Speed Printed Circuit Broads

Cyanate Esters

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

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