Synthesis of 3-phenylethynyl phenol (a novel high temperature phenyl acetylene endcapper for arylene ethers)
- Virginia Polytechnic Institute and State Univ., Blacksburg, VA (United States)
With the recent development of many high Tg polyarylene ethers as potential high performance/high temperature adhesives and composite matrices on aerospace vehicles, a need for an endcapper with very high curing temperature is very much required to improve the solvent resistance of these polymers. Presently available endcappers for arylene ethers such as nadimides, maleimides, cyanates, and acetylenes, cannot be used as the Tg`s of some of these polymers are closer or even higher than the curing temperature`s of the above endcaps. This makes processing very difficult and sometimes impossible for these materials. Here, the authors report the synthesis of 3-phenylethynyl phenol, a potential high temperature crosslinking endcapper for the high Tg polyarylene ethers. 3-Phenylethynyl phenol has been synthesized in high yields and purity, using the palladium catalyzed coupling reaction between the protected 3-bromo or iodo phenol and phenylacetylene. The yield of the reaction was found to highly dependent on the structure of the halide used, temperature of the reaction and the amount of the phenylacetylene used. The use of the protected phenol in the palladium catalyzed reaction, has been extended also towards the synthesis of 3-ethynyl phenol and protected 4-ethynyl phenols in high yields. The complete synthesis of 3-phenylethynyl phenol, 3-ethynyl phenol and protected 4-ethynyl phenol in high yields is discussed.
- OSTI ID:
- 141553
- Report Number(s):
- CONF-930304--
- Country of Publication:
- United States
- Language:
- English
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