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Browse Prior Art Database

Selective Diazotization of a Diamine

IP.com Disclosure Number: IPCOM000050629D
Original Publication Date: 1982-Nov-01
Included in the Prior Art Database: 2005-Feb-10
Document File: 2 page(s) / 44K

Publishing Venue

IBM

Related People

Heil, WP: AUTHOR

Abstract

A nonsymmetrical bis-diazo molecule can be produced by reacting a primary aromatic diamine with HBF and isoamyl nitrite to form a monoazotized fluoroborate salt. This salt is then coupled to a first organic coupling agent to form an azo dye. A second organic coupling agent may then be coupled to the remaining amino group, using the same procedure.

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Selective Diazotization of a Diamine

A nonsymmetrical bis-diazo molecule can be produced by reacting a primary aromatic diamine with HBF and isoamyl nitrite to form a monoazotized fluoroborate salt. This salt is then coupled to a first organic coupling agent to form an azo dye. A second organic coupling agent may then be coupled to the remaining amino group, using the same procedure.

Symmetrical chlorodiane blue (CDB) was synthesized by the following two- step method in order to illustrate the feasibility of this two-step coupling procedure.

The resulting fluoroborate salt (II) can be stored for a period of time, without decomposition. The stabilized fluoroborate salt can be dissolved in an appropriate solvent and coupled to an organic coupling agent (i.e., naphthol AS) as follows:

The resulting azo dye (IV) can then be azotized on the remaining amino group and coupled with an organic coupling agent (i.e., naphthol AS) as follows:

The above procedure may also be used to produce a nonsymmetrical bis- diazo molecule by utilizing two different coupling agents.

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