Claims
- 1. A process for preparing a colorant of the formula
- 2. A process according to claim 1 wherein conversion to ester or urethane is performed before bromination.
- 3. A process according to claim 1 wherein bromination is performed before conversion to ester or urethane.
- 4. A process according to claim 1 wherein conversion to ester is carried out and the resulting compound is of the formula
- 5. A process according to claim 1 wherein conversion to urethane is carried out and the resulting compound is of the formula
- 6. A process 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, wherein R1 is an alkylene group or an arylalkylene group, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula
- 7. A process 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, wherein R1 is an alkylene group or an arylalkylene group, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula
- 8. A process 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, wherein R1 is an alkylene group or an arylalkylene group, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula
- 9. A process 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, wherein R1 is an alkylene group or an arylalkylene group, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula
- 10. A process 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, wherein R1 is an alkylene group or an arylalkylene group, (3) boric acid, and (4) an optional solvent, and heating the first reaction mixture to prepare an alcohol-substituted colorant of the formula
- 11. A process according to claim 6 wherein quinizarin is present in the first reaction mixture.
- 12. A process according to claim 11 wherein the quinizarin and the leucoquinizarin are present in relative amounts of at least about 5 moles of leucoquinizarin per every 95 moles of quinizarin.
- 13. A process according to claim 11 wherein the quinizarin and the leucoquinizarin are present in relative amounts of at least about 2 moles of leucoquinizarin per every 3 moles of quinizarin.
- 14. A process according to claim 11 wherein the quinizarin and the leucoquinizarin are present in relative amounts of at least about 1 mole of leucoquinizarin per every 1 mmole of quinizarin.
- 15. A process according to claim 6 wherein no quinizarin is present in the first reaction mixture.
- 16. A process according to claim 6 wherein the alcohol-substituted aminobenzene is present in an amount of at least about 0.95 mole of alcohol-substituted aminobenzene per every one mole of (quinizarin plus leucoquinizarin).
- 17. A process according to claim 6 wherein the alcohol-substituted aminobenzene is present in an amount of no more than about 1.05 moles of alcohol-substituted aminobenzene per every one mole of (quinizarin plus leucoquinizarin).
- 18. A process according to claim 6 wherein the boric acid is present in an amount of about 1 mole of boric acid per every one mole of (quinizarin plus leucoquinizarin).
- 19. A process according to claim 6 wherein in the first reaction mixture a solvent is used which is methanol, ethanol, isopropanol, butanol, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, or a mixture thereof.
- 20. A process according to claim 6 wherein the first reaction mixture is heated to a temperature of at least about 60° C.
- 21. A process according to claim 6 wherein the first reaction mixture is heated to a temperature of no more than about 120° C.
- 22. A process according to claim 6 wherein the first reaction mixture is heated for a period of time of at least about 3 hours.
- 23. A process according to claim 6 wherein the first reaction mixture is heated for a period of time of no more than about 24 hours.
- 24. A process according to claim 6 wherein the alcohol-substituted colorant and the anhydride are present in relative amounts of at least about 1 mole of anhydride per every one mole of alcohol-substituted colorant.
- 25. A process according to claim 6 wherein the solvent in the second reaction mixture is acetic acid, propionic acid, formic acid, butyric acid, dimethyl formamide, dimethyl sulfoxide, hexamethyl phosphorus triamide, tetrahydrofuran, or a mixture thereof.
- 26. A process according to claim 6 wherein the second reaction mixture is heated to a temperature of at least about 40° C.
- 27. A process according to claim 6 wherein the second reaction mixture is heated to a temperature of no more than about 100° C.
- 28. A process according to claim 6 wherein the second reaction mixture is heated for a period of time of at least about 2.5 hours.
- 29. A process according to claim 6 wherein the second reaction mixture is heated for a period of time of no more than about 5 hours.
- 30. A process according to claim 6 wherein bromine is provided in the third reaction mixture by adding elemental bromine.
- 31. A process according to claim 6 wherein bromine is provided in the third reaction mixture by generating it in situ by the addition of a combination of a bromide salt and a bromate salt.
- 32. A process according to claim 6 wherein the ester-substituted colorant and the bromine are present in the third reaction mixture in relative amounts of at least about 2 moles of Br2 per every one mole of ester-substituted colorant.
- 33. A process according to claim 6 wherein the ester-substituted colorant and the bromine are present in the third reaction mixture in relative amounts of no more than about 4 moles of Br2 per every one mole of ester-substituted colorant.
- 34. A process according to claim 6 wherein the solvent in the third reaction mixture is acetic acid, propionic acid, formic acid, butyric acid, dimethyl formamide, dimethyl sulfoxide, hexamethyl phosphorus triamide, tetrahydrofuran, or a mixture thereof.
- 35. A process according to claim 6 wherein the third reaction mixture is initially heated to a temperature of from about 30° C. to about 40° C.
- 36. A process according to claim 6 wherein the third reaction mixture is maintained at a temperature of at least about 50° C.
- 37. A process according to claim 6 wherein the third reaction mixture is maintained at a temperature of no more than about 100° C.
- 38. A process according to claim 6 wherein the reaction between the ester-substituted colorant and the bromine is allowed to proceed for a period of time of at least about 5 hours.
- 39. A process according to claim 6 wherein the reaction between the ester-substituted colorant and the bromine is allowed to proceed for a period of time of no more than about 24 hours.
- 40. A process according to claim 6 wherein when the third reaction mixture is quenched with water, the amount of water is at least about 1.5 times as much water by volume as the volume of the reaction mixture.
- 41. A process according to claim 6 wherein the solvent in the fourth reaction mixture is N-methylpyrrolidinone, dimethyl sulfoxide, dimethyl formamide, or a mixture thereof.
- 42. A process according to claim 6 wherein the base in the fourth reaction mixture is sodium hydroxide, potassium hydroxide, or a mixture thereof.
- 43. A process according to claim 6 wherein the base in the fourth reaction mixture is present in an amount of at least about 1 mole of base per mole of (brominated ester-substituted colorant plus salt thereof).
- 44. A process according to claim 6 wherein the base in the fourth reaction mixture is present in an amount of no more than about 5 moles of base per mole of (brominated ester-substituted colorant plus salt thereof).
- 45. A process according to claim 6 wherein the water and the base are added to the fourth reaction mixture as an aqueous solution of the base.
- 46. A process according to claim 6 wherein the fourth reaction mixture is heated to a temperature of at least about 50° C.
- 47. A process according to claim 6 wherein the fourth reaction mixture is heated to a temperature of no more than about 70° C.
- 48. A process according to claim 6 wherein the fourth reaction mixture is heated for a period of time of at least about 45 minutes.
- 49. A process according to claim 6 wherein the fourth reaction mixture is heated for a period of time of no more than about 90 minutes.
- 50. A process according to claim 6 wherein, subsequent to completion of the reaction, the fourth reaction mixture is quenched with water.
- 51. A process according to claim 6 wherein the amount of water used to quench the fourth reaction mixture is at least about 3 times as much water by volume as the volume of the reaction mixture.
- 52. A process according to claim 6 wherein the brominated alcohol-substituted colorant and the carboxylic acid are present in the fifth reaction mixture in relative amounts of at least about 0.9 mole of carboxylic acid per every one mole of brominated alcohol-substituted colorant.
- 53. A process according to claim 6 wherein the brominated alcohol-substituted colorant and the carboxylic acid are present in the fifth reaction mixture in relative amounts of no more than about 2 moles of carboxylic acid per mole of brominated alcohol-substituted colorant.
- 54. A process according to claim 6 wherein in the fifth reaction mixture an esterification catalyst is used which is para-toluene sulfonic acid, dibutyl tin dilaurate, or a mixture thereof.
- 55. A process according to claim 6 wherein in the fifth reaction mixture an esterification catalyst is used in an amount of at least about 0.05 mole of esterification catalyst per every one mole of brominated alcohol-substituted colorant.
- 56. A process according to claim 6 wherein in the fifth reaction mixture an esterification catalyst is used in an amount of no more than about 0.5 mole of esterification catalyst per mole of brominated alcohol-substituted colorant.
- 57. A process according to claim 6 wherein the solvent in the fifth reaction mixture is xylene, toluene, benzene, chlorobenzene, nitrobenzene, dichlorobenzene, or a mixture thereof.
- 58. A process according to claim 6 wherein the fifth reaction mixture is heated to a temperature of at least about 100° C.
- 59. A process according to claim 6 wherein the fifth reaction mixture is heated to a temperature of no more than about 130° C.
- 60. A process according to claim 6 wherein the fifth reaction mixture is heated for a period of time of at least about 2 hours.
- 61. A process according to claim 6 wherein the fifth reaction mixture is heated for a period of time of no more than about 72 hours.
- 62. A process according to claim 6 wherein Y is a hydrogen atom.
- 63. A process according to claim 6 wherein Y is a bromine atom.
- 64. A process according to claim 6 wherein n is 2.
- 65. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 66. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 67. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 68. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 69. A process according to claim 6 wherein R1 is an unsubstituted alkylene group or an unsubstituted arylalkylene group.
- 70. A process according to claim 6 wherein R1 is a substituted alkylene group or a substituted arylalkylene group.
- 71. A process according to claim 6 wherein hetero atoms selected from oxygen, nitrogen, sulfur, silicon, or phosphorus are present in the R1 group.
- 72. A process according to claim 6 wherein no hetero atoms are present in the R1 group.
- 73. A process according to claim 6 wherein R1 is an alkylene group having at least about 2 carbon atoms.
- 74. A process according to claim 6 wherein R1 is of the formula
- 75. A process according to claim 6 wherein R2′ is an unsubstituted alkyl group, an unsubstituted aryl group, an unsubstituted arylalkyl group, or an unsubstituted alkylaryl group.
- 76. A process according to claim 6 wherein R2′ is a substituted alkyl group, a substituted aryl group, a substituted arylalkyl group, or a substituted alkylaryl group.
- 77. A process according to claim 6 wherein hetero atoms selected from oxygen, nitrogen, sulfur, silicon, or phosphorus are present in the R2′ group.
- 78. A process according to claim 6 wherein no hetero atoms are present in the R2′ group.
- 79. A process according to claim 6 wherein R2′ is a linear alkyl group having an average of about 50 carbon atoms.
- 80. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 81. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 82. A process according to claim 6 wherein the second ester-substituted colorant is of the formula
- 83. A process according to claim 7 wherein R1 is of the formula
- 84. A process according to claim 7 wherein R2′ is
- 85. A process according to claim 7 wherein R2′ is
- 86. A process according to claim 7 wherein the brominated ester-substituted colorant and the salt thereof are of the formulae
- 87. A process according to claim 7 wherein the brominated ester-substituted colorant and the salt thereof are of the formulae
- 88. A process according to claim 8 wherein R1 is of the formula
- 89. A process according to claim 8 wherein R2′ is
- 90. A process according to claim 8 wherein R2′ is
- 91. A process according to claim 8 wherein the brominated ester-substituted colorant and the salt thereof are of the formulae
- 92. A process according to claim 8 wherein the brominated ester-substituted colorant and the salt thereof are of the formulae
- 93. A process according to claim 9 wherein R1 is of the formula
- 94. A process according to claim 9 wherein R2′ is
- 95. A process according to claim 9 wherein R2′ is
- 96. A process according to claim 9 wherein the brominated urethane-substituted colorant and the salt thereof are of the formulae
- 97. A process according to claim 9 wherein the brominated urethane-substituted colorant and the salt thereof are of the formulae
- 98. A process according to claim 10 wherein R1 is of the formula
- 99. A process according to claim 10 wherein R2′ is
- 100. A process according to claim 10 wherein R2′ is
- 101. A process according to claim 10 wherein the brominated urethane-substituted colorant and the salt thereof are of the formulae
- 102. A process according to claim 10 wherein the brominated urethane-substituted colorant and the salt thereof are of the formulae
Cross-reference is made to the following copending applications:
[0001] Copending Application U.S. Ser. No. ______ (not yet assigned; Attorney Docket No. D/A2341), filed concurrently herewith, entitled “Colorant Compounds,” with the named inventors Jeffery H. Banning and C. Wayne Jaeger, the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
4
[0002] 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, and X is (a) a hydrogen atom, (b) a group of the formula
5
[0003] wherein R2 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, (c) an alkyleneoxy, aryleneoxy, arylalkyleneoxy, or alkylaryleneoxy group, or (d) a group of the formula
6
[0004] wherein R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group.
[0005] Copending Application U.S. Ser. No. ______ (not yet assigned; Attorney Docket No. D/A2341Q), filed concurrently herewith, entitled “Phase Change Inks,” with the named inventors C. Wayne Jaeger and Jeffery H. Banning, the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula
7
[0006] 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, and X is (a) a hydrogen atom, (b) a group of the formula
8
[0007] wherein R2 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, (c) an alkyleneoxy, aryleneoxy, arylalkyleneoxy, or alkylaryleneoxy group, or (d) a group of the formula
9
[0008] wherein R4 is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group.