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Effects of o-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins
Macromolecules ( IF 5.1 ) Pub Date : 2015-05-14 00:00:00 , DOI: 10.1021/acs.macromol.5b00496 Benjamin G. Harvey 1 , Andrew J. Guenthner 2 , William W. Lai 1 , Heather A. Meylemans 1 , Matthew C. Davis 1 , Lee R. Cambrea 1 , Josiah T. Reams 3 , Kevin R. Lamison 3
Macromolecules ( IF 5.1 ) Pub Date : 2015-05-14 00:00:00 , DOI: 10.1021/acs.macromol.5b00496 Benjamin G. Harvey 1 , Andrew J. Guenthner 2 , William W. Lai 1 , Heather A. Meylemans 1 , Matthew C. Davis 1 , Lee R. Cambrea 1 , Josiah T. Reams 3 , Kevin R. Lamison 3
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Renewable phenols derived from biomass sources often contain methoxy groups that alter the properties of derivative polymers. To evaluate the impact of o-methoxy groups on the performance characteristics of cyanate ester resins, three bisphenols derived from the renewable phenol creosol were deoxygenated by conversion to ditriflates followed by palladium-catalyzed elimination and hydrolysis of the methoxy groups. The deoxygenated bisphenols were then converted to the following cyanate ester resins: bis(4-cyanato-2-methylphenyl)methane (16), 4,4′-(ethane-1,1′-diyl)bis(1-cyanato-3-methylbenzene) (17), and 4,4′-(propane-1,1′-diyl)bis(1-cyanato-3-methylbenzene) (18). The physical properties, cure chemistry, and thermal stability of these resins were evaluated and compared to those of cyanate esters derived from the oxygenated bisphenols. 16 and 18 had melting points 37 and >95 °C lower, respectively, than the oxygenated versions, while 17 had a melting point 14 °C higher. The Tg’s of thermosets generated from the deoxygenated resins ranged from 267 to 283 °C, up to 30 °C higher than the oxygenated resins, while the onset of thermal degradation was 50–80 °C higher. The deoxygenated resins also exhibited water uptakes up to 43% lower and wet Tgs up to 37 °C higher than the oxygenated resins. TGA-FTIR of thermoset networks derived from 16–18 revealed a different decomposition mechanism compared to the oxygenated resins. Instead of a low-temperature pathway that resulted in the evolution of phenolic compounds, 16–18 had significantly higher char yields and decomposed via evolution of small molecules including isocyanic acid, CH4, CO2, and NH3.
中文翻译：
的影响Ø在性能和可再生高温氰酸酯树脂的热稳定性-甲氧基组
源自生物质来源的可再生酚通常含有甲氧基，这些甲氧基会改变衍生物聚合物的性能。为了评估邻甲氧基对氰酸酯树脂性能特性的影响，将衍生自可再生酚甲酚的三种双酚脱氧，方法是转化为双三氟甲磺酸酯，然后用钯催化消除和水解甲氧基。然后将脱氧的双酚转化为以下氰酸酯树脂：双（4-氰基-2-甲基苯基）甲烷（16），4,4'-（乙烷-1,1'-二基）双（1-氰基-3）甲基苯）（17），和4,4' - （丙烷-1,1'-二基）二（1-氰-3-甲基苯）（18）。对这些树脂的物理性质，固化化学性质和热稳定性进行了评估，并将其与衍生自氧化双酚的氰酸酯进行了比较。16和18的熔点分别比含氧化合物低37和> 95°C，而17的熔点高14。脱氧树脂产生的热固性材料的T g为267至283°C，比含氧树脂高出30°C，而热降解的起始温度则高出50–80°C。脱氧树脂还显示出比含氧树脂低43％的吸水率和高达37°C的湿热T g。热固性网络的TGA-FTIR来源于16 - 18相比，氧化的树脂揭示了不同分解机理。代替低温途径，导致酚类化合物的演变，16 - 18有显著较高焦炭产率和通过小分子，包括异氰酸，CH的进化分解4，CO 2和NH 3。
更新日期：2015-05-14
中文翻译：
的影响Ø在性能和可再生高温氰酸酯树脂的热稳定性-甲氧基组
源自生物质来源的可再生酚通常含有甲氧基，这些甲氧基会改变衍生物聚合物的性能。为了评估邻甲氧基对氰酸酯树脂性能特性的影响，将衍生自可再生酚甲酚的三种双酚脱氧，方法是转化为双三氟甲磺酸酯，然后用钯催化消除和水解甲氧基。然后将脱氧的双酚转化为以下氰酸酯树脂：双（4-氰基-2-甲基苯基）甲烷（16），4,4'-（乙烷-1,1'-二基）双（1-氰基-3）甲基苯）（17），和4,4' - （丙烷-1,1'-二基）二（1-氰-3-甲基苯）（18）。对这些树脂的物理性质，固化化学性质和热稳定性进行了评估，并将其与衍生自氧化双酚的氰酸酯进行了比较。16和18的熔点分别比含氧化合物低37和> 95°C，而17的熔点高14。脱氧树脂产生的热固性材料的T g为267至283°C，比含氧树脂高出30°C，而热降解的起始温度则高出50–80°C。脱氧树脂还显示出比含氧树脂低43％的吸水率和高达37°C的湿热T g。热固性网络的TGA-FTIR来源于16 - 18相比，氧化的树脂揭示了不同分解机理。代替低温途径，导致酚类化合物的演变，16 - 18有显著较高焦炭产率和通过小分子，包括异氰酸，CH的进化分解4，CO 2和NH 3。
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