US 7,524,979 B2
Methods of making colorant compounds
C. Wayne Jaeger, Beaverton, Oreg. (US); and Jeffery H. Banning, Hillsboro, Oreg. (US)
Assigned to Xerox Corporation, Norwalk, Conn. (US)
Filed on Feb. 21, 2006, as Appl. No. 11/358,010.
Application 11/358010 is a division of application No. 10/260379, filed on Sep. 27, 2002, granted, now 7,053,227.
Prior Publication US 2006/0178458 A1, Aug. 10, 2006
Int. Cl. C09B 1/16 (2006.01)
U.S. Cl. 552—247  [552/243; 552/244; 552/248] 66 Claims
 
1. A process for preparing a colorant of the formula

OG Complex Work Unit Drawing
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

OG Complex Work Unit Drawing
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

OG Complex Work Unit Drawing
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.