Di(cyanate Ester) Networks Based on Alternative Fluorinated Bisphenols with Extremely Low Water Uptake

Corley, Cynthia A.; Guenthner, Andrew J.; Sahagun, Christopher M.; Lamison, Kevin R; Reams, Josiah T; Hassan, Mohammad K.; Morgan, Sarah E.; Iacono, Scott T.; Mabry, Joseph M.

doi:10.1021/mz400520s

Cited by 33 publications

(29 citation statements)

References 43 publications

(58 reference statements)

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“…Water uptake can be alleviated in part through CE monomer development and the incorporation of functional groups that inhibit water absorption through steric or hydrophobic interactions . For example, our research group and others have shown that incorporating some degree of fluorination within CE monomers results in CEs that display some of the lowest water uptake reported to date . Additionally, it has been shown that high conversions of the cyanate groups yields networks with more desirable physical properties, including reduced water uptake .…”

Section: Introductionmentioning

confidence: 99%

“…26 For example, our research group and others have shown that incorporating some degree of fluorination within CE monomers results in CEs that display some of the lowest water uptake reported to date. 27,28 Additionally, it has been shown that high conversions of the cyanate groups yields networks with more desirable physical properties, including reduced water uptake. 29,30 When unreacted cyanate groups are present, they can decompose or react with water leading to further degradation and blistering within the network.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of siloxane‐based cyanate ester elastomers from readily available materials: a top‐down approach

Jennings

Morey

Guenthner

et al. 2016

Polymer International

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A number of siloxane‐based cyanate ester (SiCE) elastomers were prepared from commercially available starting reagents employing a hydrosilylation reaction. Each elastomer was designed to utilize 2,4,6‐tris(allyloxy)‐1,3,5‐triazine as a crosslinker and multifunctional vinyl component in the hydrosilylation reaction, ensuring that the triazine rings were completely formed, and thus the elastomers resemble fully cured cyanate ester networks. The hydride‐terminated siloxane components used were varied from small‐molecule siloxanes to pre‐polymers of different molecular weights. Attenuated total reflectance Fourier transform infrared analysis confirmed the successful hydrosilylation reaction and complete curing of the SiCE elastomers via functional group analysis. Thermal characterization by thermogravimetric analysis and differential scanning calorimetry demonstrated that thermal properties of the elastomers could be tailored depending on the type of siloxane component that was utilized. The gel content of the elastomers was also determined. Investigations into the effects of a platinum catalyst on the elastomers determined that the presence of the catalyst affected the thermochemical stability of the SiCE elastomers. Published 2016. This article is a U.S. Government work and is in the public domain in the USA.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of siloxane‐based cyanate ester elastomers from readily available materials: a top‐down approach

Jennings

Morey

Guenthner

et al. 2016

Polymer International

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“…1-10 These materials usually show high thermostability, good mechanical properties, excellent insulating behavior and moisture resistance. [11][12][13][14][15][16][17] Therefore, they have played very important roles in the materials utilized in aerospace, electrical and microelectronics industries. However, most of the polymers show unsatisfactory processability, which needs to be improved.…”

Section: Introductionmentioning

confidence: 99%

A spiro-centered thermopolymerizable fluorinated macromonomer: synthesis and conversion to the high performance polymer

et al. 2017

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A new spiro-centered thermopolymerizable fluorinated macromonomer is reported here. This fourfunctional macromonomer is synthesized by a convergent strategy, and shows a low melting point (93 C) and good solubility in the common organic solvents. When heated to a high temperature, the macromonomer converts into a cross-linked network (PD 1 ), which exhibits a T g of near 316 C and a 5% weigh loss at a temperature of 417 C in N 2 . PD 1 also shows a low dielectric constant (D k ¼ 2.58 at 30 MHz) and high hydrophobicity (a water contact angle of q ¼ 98 ), as well as low water uptake (about 0.45%, kept in boiling water for 72 h). These results suggest that the macromonomer has a potential application in the production of the high performance polymers, in particular, it is very suitable for encapsulation resins or the coatings utilized in the microelectronics industry.Scheme 1 Procedure for the synthesis and conversion of the new monomer D 1 .

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“…38−44 Alternatively, similar effects can be obtained by altering the bridging groups between rings. 45 −56 In a recent paper we described the synthesis and characterization of a series of bis(cyanate) esters derived from the renewable phenol creosol (2-methoxy-4-methylphenol). 57 Unlike the majority of modified cyanate ester resins that have aliphatic or aromatic substituents, the resins derived from creosol have methoxy groups ortho to the cyanate ester groups.…”

Section: ■ Introductionmentioning

confidence: 99%

Effects of o-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins

et al. 2015

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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 T g '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 T g s 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, CH 4 , CO 2 , and NH 3 .

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Di(cyanate Ester) Networks Based on Alternative Fluorinated Bisphenols with Extremely Low Water Uptake

Cited by 33 publications

References 43 publications

Synthesis and characterization of siloxane‐based cyanate ester elastomers from readily available materials: a top‐down approach

Synthesis and characterization of siloxane‐based cyanate ester elastomers from readily available materials: a top‐down approach

A spiro-centered thermopolymerizable fluorinated macromonomer: synthesis and conversion to the high performance polymer

Effects of o-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins

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