Synthesis, characterization, and cure chemistry of high performance phosphate cyanate ester resins

Three thermosetting cyanate ester resins with phosphate cores have been synthesized from chlorophosphates by a straightforward, three-step approach. A p -substituted bis(cyanate) ester generated by this route ( PhosCy ) was cured to give a thermoset material with a T g of 223 °C and a char yield of...

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Bibliographic Details
Published in:RSC advances 2015-01, Vol.5 (91), p.74712-74719
Main Authors: Harvey, Benjamin G., Chafin, Andrew C., Garrison, Michael D., Cambrea, Lee R., Groshens, Thomas J.
Format: Article
Language:English
Subjects:
Combustion
Cyanates
Esters
Flame resistant materials
Phosphates
Polymers
Resins
Thermosetting resins
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Summary:Three thermosetting cyanate ester resins with phosphate cores have been synthesized from chlorophosphates by a straightforward, three-step approach. A p -substituted bis(cyanate) ester generated by this route ( PhosCy ) was cured to give a thermoset material with a T g of 223 °C and a char yield of 47% in air, while the m -substituted version ( MPhosCy ) yielded a thermoset with a T g of only 131 °C and a char yield of 65% in air. The low T g of the MPhosCy thermoset is attributed to a unique intramolecular cyclization of the cyanate ester groups, while the high char yield is attributed to a high temperature cross-linking reaction involving the phosphate core. To further explore this class of materials, a trifunctional phosphate cyanate ester ( PhosCy3 ) was prepared from POCl 3 . This material was cured to generate a thermoset with an impressive T g of >360 °C and a char yield of 67% in air. All three hybrid resins can potentially be used in fire-resistant composite materials or as protective surface coatings for conventional polymers.
ISSN:2046-2069
2046-2069
DOI:10.1039/C5RA16197E