Preparation of 4,6-diaminoresorcinol through a bisazoarylresorci

Details Preparation of 4,6-diaminoresorcinol through a bisazoarylresorci Preparation of 4,6-diaminoresorcinol through a bisazoarylresorci

1994-02-24

1995-09-26

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

534688, 564442, 564443, C07C21302

Patent

active

054535425

ABSTRACT:
The present invention is a method of preparing a 4,6-bisarylazoresorcinol comprising reacting an aryldiazonium salt and resorcinol in the presence of a base and a reaction medium containing water and a water-miscible solvent at a temperature in the range of about -5.degree. C to about -60.degree. C. The present invention is also a method of preparing a 2-substituted 4,6-bisarylazoresorcinol comprising reacting an aryldiazonium salt with a 2-substituted resorcinol. The 4,6-bisarylazoresorcinol or 2-substituted 4,6-bisarylazoresorcinol can then be hydrogenated to a 4,6-diaminoresorcinol, which is a precursor to polybisbenzoxazoles (PBOs), polymers which are useful as insulators, solar arrays, and tear-resistant gloves.

REFERENCES:
patent: 4766244 (1988-08-01), Lysenko
patent: 4982001 (1991-01-01), Lysenko et al.
"Polybenzothiazoles and Polybenxoxazoles" by Paul D. Sybert; printed in vol. 11 Encyclopedia of Polymer Science and Engineering .COPYRGT.1988 by John Wiley & Sons, pp. 601-647.
Advanced Organic Chemistry 4th Edition by Jerry March .COPYRGT.John Wiley & Sons, p. 1224.
"General Base Catalysis of Orientation in Resorcinol Couplings" by H. F. Hodson et al.; printed in Helvetica Chimica Acta, vol. XLI, Fasciculus VI (1958)--Nr. 195, pp. 1816-1823.
"Isomeric Phenyl Dis-Azo Resorcinols" by Liebermann and Kostanecki, printed in Berichte der Deut Deutschen Chemischen Gesellschaft .COPYRGT.1988, vol. XX, pp. 3114-3119.
"Some Disazo and Trisazo Derivatives of Resorcin" by W. R. Orndorff et al.; printed in American Chemical Journal, vol. XLIV No. 1 .COPYRGT.1910.

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