US 7,524,979 B2Granted

Methods of making colorant compounds

AssigneeXerox Corporation

InventorsC. Wayne Jaeger, Jeffery H. Banning

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Abstract

A process for preparing a colorant of the formula which comprises preparing a first reaction mixture by admixing leucoquinizarin and, optionally, quinizarin, an aminobenzene substituted with an alcohol group of the formula —R1—OH, boric acid, and an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula followed by converting the colorant thus prepared to either an ester-substituted colorant by reaction with an esterification compound which is either an anhydride of the formula or an acid of the formula R2COOH in the presence of an optional esterification catalyst, or a urethane-substituted colorant by reaction with an isocyanate compound of the formula R4—N═C═C═O, and brominating the colorant thus prepared, wherein either conversion to ester or urethane can be performed before bromination or bromination can be performed before conversion to ester or urethane.

Claims66

Dependent claims

A process for preparing a colorant of the formula

wherein Y is a hydrogen atom or a bromine atom, n is an integer of 0, 1, 2, 3, or 4, R1 is an alkylene group or an arylalkylene group, R2 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, which comprises (a) preparing a first reaction mixture by admixing (1) leucoquinizarin and, optionally, quinizarin, (2) an aminobenzene substituted with an alcohol group of the formula —R1—OH, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula
followed by (b) converting the colorant thus prepared to either (i) an ester-substituted colorant by reaction with an esterification compound which is either (A) an anhydride of the formula
or (B) an acid of the formula R2COOH in the presence of an optional esterification catalyst, or (ii) a urethane-substituted colorant by reaction with an isocyanate compound of the formula
R4—N═C═O,
and (c) brominating the colorant thus prepared, wherein either conversion to ester or urethane can be performed before bromination or bromination can be performed before conversion to ester or urethane.

2 more elements

Dependencies are inferred from the claim text.