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characteristics by controlling the double bond geometry. The
naturally occurring, phytofeedstock resveratrol could be
transformed by a simple, two-step process into the new com-
pound cRes tricyanate (2) in 69% yield. The new thermoset-
ting resin had a melting point 93 8C less than its trans
isomeric form. Apart from this difference, the polycyanurate
of 2 had equal or better thermal stability characteristics
10 J. J. Cash, M. C. Davis, M. D. Ford, T. J. Groshens, A. J.
Guenthner, B. G. Harvey, K. R. Lamison, J. M. Mabry, H. A.
Meylemans, J. T. Reams, Polym. Chem. 2013, 4, 3859–3865.
1
1 E. L. Eliel, J. J. Engelsmen, J. Chem. Educ. 1996, 73, 903–
9
05 and references therein.
1
2 cis-stilbene distills (140 8C @ 20 torr) without isomerization
see: R. E. Buckles, N. G. Wheeler, Org. Synth. 1953, 33, 88.
1
3 J. Saltiel, S. Ganapathy, C. Werking, J. Phys. Chem. 1987,
(
Tg > 350 8C; char yield in air 5 73%) as compared with the
trans isomer. The material even had good stability up to 900
C (char yield 60%) by MCC analysis. Preliminary flammabili-
9
1, 2755–2758.
1
4 D. Artl, A. Bader, V. Eckhard, K.-J. Idel, F.-G. Kleiner, (Bayer).
8
U.S. Patent 5,136,013, August 4, 1992.
5 Prudent Practices in the Laboratory: Handling and Disposal
ty screening of polycyanurate 2 by MCC showed that
although there is a strong Qmax peak at ꢀ430 8C, the new
material has a 70% chance of passing the FAR25 limits in
OSU fire calorimeter. Thus, monomer 2 could be useful in
manufacturing PMCs where resistance to high temperatures
is critical. Further studies with monomer 2 will be to exam-
ine the material’s thermal stability to “hot/wet” conditions
and with larger quantities of 2 prepare resin/fiberglass lami-
na for cone and/or OSU fire calorimeter experiments.
1
of Chemicals; National Academy Press: Washington, 1995; pp
288–289.
16 P. Patnaik, A Comprehensive Guide to the Hazardous Prop-
erties of Chemical Substances, 3rd ed.; Wiley: New York, 2007;
pp 328–329.
1
7 R. P. Pohanish, Sittig’s Handbook of Toxic and Hazardous
Chemicals and Carcinogens, 6th ed.; Elsevier: Oxford, 2012; pp
8
02–804.
1
8 B. J. Frame, Characterization and Process Development of
Cyanate Ester Resin Composites, Oak Ridge National Laborato-
ry, ORNL/CP-101112, March 1999.
1
9 ASTM Standard D 7309-11,2011, “Standard test method for
determining flammability characteristics of plastics and other
solid materials using microscale combustion calorimetry,”
ACKNOWLEDGMENTS
The authors gratefully acknowledge the generous financial sup-
port from the Office of Naval Research through the In-House
Independent Research (ILIR) program. Thanks to Drs. Lawrence
C. Baldwin and Randall McClain (China Lake) for assistance with
the photochemical reactor system, thermogravimetric experi-
ments and photography. Thanks to Mary Ray and Mara Bowen of
the NAWC Technical Library (China Lake) for collecting several
of the literature citations.
2
0 G. S. Jayatilake, H. Jayasuriya, E. S. Lee, N. M.
Koonchanok, R. L. Geahlen, C. L. Ashendel, J. L. McLaughlin,
C.-J. Chang, J. Nat. Prod. 1993, 56, 1805–1810.
2
2
1 E. Bernard, P. Britz-McKibbin, N. Gernigon, J. Chem. Educ.
007, 84, 1159–1161.
2
2 A. Francioso, A. Boffi, C. Villani, L. Manzi, M. D’Erme, A.
Macone, L. Mosca, J. Org. Chem. 2014, 79, 9381–9384.
2
3 M. Deak, H. Falk, Monatsh. Chem. 2003, 134, 883–888.
2
4 L. A. Stivala, M. Savio, F. Carafoli, P. Perucca, L. Bianchi, G.
REFERENCES AND NOTES
Maga, L. Forti, U. M. Pagnoni, A. Albini, E. Prosperi, V.
Vannini, J. Biol. Chem. 2001, 276, 22586–22594.
1
2
M. R. Kessler, Polym. Rev. 2012, 52, 229–233.
2
5 V. Cardile, R. Chillemi, L. Lombardo, S. Sciuto, C. Spatafora,
C. Tringali, Z. Naturforsch. C 2007, 62, 189–195.
6 G. R. Pettit, S. B. Singh, M. L. Niven, E. Hamel, J. M.
M. A. Masuelli, In Fiber Reinforced Polymer – The Tech-
2
Schmidt, J. Nat. Prod. 1987, 50, 119–131.
27 G. R. Pettit, M. R. Rhodes, D. L. Herald, E. Hamel, J. M.
Schmidt, R. K. Pettit, J. Med. Chem. 2005, 48, 4087–4099.
28 E. Grigat, R. P u€ tter, Chem. Ber. 1964, 97, 3012–3017.
3
4
D. Mathijsen, Reinforced Plast. 2016, 60, 38–44.
29 J. Binoy, J. P. Abraham, I. H. Joe, V. S. Jayakumar, G. R.
Pettit, O. F. Nelson, J. Raman Spectrosc. 2004, 35, 939–946.
US Department of Transportation, Aviation Maintenance
ꢀ
Technician Handbook-Airframe (FAA-H-8033-31); Federal Avia-
30 Z. Mei c´ , T. Suste, G. Baranovi c´ , V. Smre cˇ ki, S. Holly, G.
tion Administration, 2012; Vol. 1, Chapter 7.
Keresztury, J. Mol. Struct. 1995, 348, 229–232.
5
6
D. Carney, Automot. Eng. Int. 2012, 120, 10–12.
31 A. W. Snow, In Chemistry and Technology of Cyanate Ester Res-
ins; I. Hamerton, Ed.; Chapman & Hall: New York, 1994; Chapter 2.
J.-P. Pascault, R. J. J. Williams, In Thermosets: Structure,
Properties and Applications; Q. Guo, Ed.; Elsevier: New York,
32 B. Cassel, B. Twombly, In Materials Characterization by
Thermomechanical Analysis; A. T. Riga, C. M. Neag, Eds.;
ASTM Publication Code 04-011360-50, 1991; pp 108–119.
2012; Chapter 1; pp 3–27.
7
A. M. Coppola, L. G. Warpinski, S. P. Murray, N. R. Sottos, S.
R. White, Compos. A 2016, 82, 170–179.
G. A. Schoeppner, M. S. Tillman, In Long-Term Durability of
33 L. Cambrea, M. C. Davis, T. J. Groshens, A. J. Guenthner, K.
R. Lamison, J. M. Mabry, J. Polym. Sci. Part A: Polym. Chem.
8
2
010, 48, 4547–4554.
Polymeric Matrix Composites; K. V. Pochiraju, G. Tandon, G. A.
Schoeppner, Eds.; Springer: New York, 2012; Chapter 11.
34 Z. Mei c´ , H. G u€ sten, Spectrochim. Acta. 1978, 34A, 101–111.
35 J. F. Arenas, I. L. Toc oꢁ n, J. C. Otero, J. I. Marcos, J. Phys.
Chem. 1995, 99, 11392–11398.
9
I. Hamerton, In Chemistry and Technology of Cyanate Ester Res-
ins; I. Hamerton, Ed.; Chapman & Hall: New York, 1994; Chapter 1.
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