A new room‐temperature liquid, high‐performance tricyanate ester

Cambrea, Lee R.; Davis, Matthew C.; Groshens, Thomas J.; Guenthner, Andrew J.; Lamison, Kevin R; Mabry, Joseph M.

doi:10.1002/pola.24246

Cited by 17 publications

(16 citation statements)

References 30 publications

(21 reference statements)

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“…In addition, FTIR analysis of the polycyanurate after 280 °C “post‐cure” show that the cyanate ester peak found at 2250 cm −1 had all but disappeared and the typical strong bands associated with cyanurate ring at 1360 and 1560 cm −1 had appeared, Figure …”

Section: Resultsmentioning

confidence: 98%

Processable cyanate ester resin from Cis resveratrol

Cambrea

Davis

Garrison

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Trans resveratrol isomerizes to cis resveratrol (cRes) with ultra-violet light and undergoes cyanation to the new compound cRes tricyanate (2). Monomer 2 polymerizes to a polycyanurate that is remarkably stable to heat with a glass transition temperature > 350 8C and char yield of 73% in air up to 600 8C. The monomer 2 melts at <80 8C with a wide processing window before polymerization. The new thermosetting resin made from a natural product is a useful matrix material for polymer matrix composites requiring high-performance characteristics. V C 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 971-980

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Section: Resultsmentioning

confidence: 98%

Processable cyanate ester resin from Cis resveratrol

Cambrea

Davis

Garrison

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…The 1,1-di- 208 www.chemsuschem.org phenylethane framework typically results in depressed melting points compared to methylene or 2,2-diphenylpropane linkages. [19] Despite this discrepancy, the melting point exhibited a drastic decrease upon extension of the reaction from acetaldehyde to propionaldehyde, and 5 was isolated as a viscous oil. For applications as precursors to thermosetting composites, lower melting resins should allow simplified and lower-cost fabrication methods.…”

Section: Structures and Properties Of Bisphenolsmentioning

confidence: 99%

Synthesis of Renewable Bisphenols from Creosol

2011

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A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short-chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yields and purities without resorting to solvent-intense purification methods. Zinc acetate was shown to be a selective catalyst for the ortho-coupling of formaldehyde, but was unreactive when more sterically demanding aldehydes were used. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the hydroxyl group. The acid solutions could be recycled and reused multiple times without decrease in activity or yield.

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“…Snow and coworkers prepared oligodimethylsiloxanes linked cyanate esters with low dielectric characteristic 4. Davis and coworkers used racemic/diastereomeric concept to prepare a liquid‐type tricyanate ester for favorable processing characteristic and enhanced thermomechanical performance in wet environments 5. Wang and coworkers prepared phenolphthalein‐based cyanate esters with high‐ T g for higher temperature applications 6.…”

Section: Introductionmentioning

confidence: 99%

“…Although poly(cyanate esters) display promising properties, the lack of flame retardancy is a drawback of cyanate ester for electronic applications, where meeting a flame retardancy standard, UL‐94 V‐0, is required. Literatures have reported that the flame retardancy of cyanate esters can be greatly enhanced by the incorporation of phosphorus element 5, 9–18…”

Section: Introductionmentioning

confidence: 99%

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

Lin

Tian

et al. 2011

J. Polym. Sci. A Polym. Chem.

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We reveal a route for the preparation of phosphinated bisphenol, 1,1-bis(4-hydroxyphenyl)-1-(6-oxido-6H-dibenz <1,2> oxaphosphorin-6-yl)ethane (2), via a one-pot reaction of 1,1,1-tris(4-hydroxyphenyl)ethane and 9,10-dihydro-9oxa-10-phosphaphenanthrene 10-oxide (DOPO) in the catalysis of p-toluenesulfonic acid. A two-step reaction mechanism, acid-fragmentation of 1,1,1-tris(4-hydroxyphenyl)ethane followed by nucleophilic addition of DOPO, is proposed for the synthesis. Based on (2), a dicyanate ester derivative, 1,1-bis(4cyanatophenyl)-1-(6-oxido-6H-dibenz <1,2> oxaphosphorin-6-yl)ethane (3) was prepared and co-cured with a commercially available dicyanate ester, the dicyanate ester of bisphenol A (BACY). Experimental data show that incorporating (3) into BACY enhances the flame retardancy and dielectric properties with little penalty to the thermal properties. A thermoset with T g 274 C, coefficient of thermal expansion (CTE) 49 ppm/ C, D k 3.04 (1 GHz), T d (5%,) N 2 : 435 C, air: 424 C, and UL-94 V-0 rating can be achieved via this approach.

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A new room‐temperature liquid, high‐performance tricyanate ester

Cited by 17 publications

References 30 publications

Processable cyanate ester resin from Cis resveratrol

Processable cyanate ester resin from Cis resveratrol

Synthesis of Renewable Bisphenols from Creosol

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

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