Porphyrin chromophore and dendrimer ink composition

• US 5,256,193 A
• Filed: 06/25/1992
• Issued: 10/26/1993
• Est. Priority Date: 06/25/1992
• Status: Expired due to Fees

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Breton, Marcel P., Winnik, Francoise M., Davidson, Anthony R.
• Primary Examiner(s): Bell, Mark L.
• Assistant Examiner(s): EINSMANN, MARGARET V
• Application Number:
  US07/904,318
• Time in Patent Office: 488 Days
• Field of Search: 106/21 A, 106/19 F-19 R, 106/15.05, 106/17
• US Class Current: 106/31.46
• CPC Class Codes: B41M 3/06 Veined printings; Fluorescent printings; Stereoscopic images; Imitated patterns, e.g. tissues, textiles
• CPC Class Codes: B41M 3/144 using fluorescent, luminescent or iridescent effects
• CPC Class Codes: C09D 11/30 Inkjet printing inks
• CPC Class Codes: C09D 11/50 Sympathetic, colour changing or similar inks
• CPC Class Codes: Y10S 424/16 Dendrimers and dendritic polymers

Abstract

An ink composition comprised of a solution comprised of a dye comprised of a porphyrin chromophore and a dendrimer.

Claims

1. An ink composition comprised of a solution comprised of a dye comprised of a porphyrin chromophore and a dendrimer;

and wherein the solution contains a liquid vehicle present in an amount of from about 85 to about 99.5 percent by weight, the dye is present in an amount of from about 0.0005 to about 1.0 weight percent, and the dendrimer is present in an amount of from about 0.05 to about 10 weight percent.

2. An ink in accordance with claim 1 wherein the solution contains water.

3. An ink in accordance with claim 1 wherein the solution contains water, a humectant, and a biocide.

4. An ink in accordance with claim 1 wherein the dye is 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetraacetate salt.

5. An ink in accordance with claim 1 wherein the dye is selected from the group consisting of 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetra-p-tosylate, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetrachloride, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetrabromide, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetra-acetate, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetra-perchlorate, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetra-fluoroborate, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetra-perchlorate, 5,10,15,20-tetrakis-(1-methyl-4-pyridyl)-21H,23H-porphine tetra-triflate, 5,10,15,20-tetrakis-(1-hydroxymethyl-4-pyridyl)-21H,23H-porphine tetra-p-tosylate, 5,10,15,20-tetrakis-[1-(2-hydroxyethyl)-4-pyridyl]-21H,23H-porphine tetrachloride, 5,10,15,20-tetrakis-[1-(3-hydroxypropyl)-4-pyridyl]-21H,23H-porphinetetra-p-tosylate, 5,10,15,20-tetrakis-[1-(2-hydroxypropyl)-4-pyridyl]-21H,23H-porphine tetra-p-tosylate, 5,10,15,20-tetrakis-[1-(2-hydroxyethoxyethyl)-4-pyridyl]-21H,23H-porphine tetra-p-tosylate, 5,10,15,20-tetrakis-[1-(2-hydroxyethoxypropyl)-4-pyridyl]-21H,23H-porphine tetra-p-tosylate, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetra-p-tosylate, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetrachloride, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetrabromide, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetra-acetate, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetraperchlorate, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetra-fluoroborate, 5,10,15,20-tetrakis-[4-(trimethylammonio)phenyl]-21H,23H-porphine tetra-triflate, meso-(N-methyl-X-pyridinium)_n -(phenyl)4-n-21H,23H-porphine tetra-p-tosylate, where n is the integer 0, 1, 2, or 3, and wherein X is 4-meso-tetrakis-[o-(N-methylnicotinamido)phenyl]-21H,23H-porphine tetra-methyl sulfonate, 5,10,15,20-tetrakis-(2-sulfonatoethyl-4-pyridyl)-21H,23H-porphine chloride, 5,10,15,20-tetrakis-(carboxymethyl-4-pyridyl)-21H,23H-porphine chloride, 5,10,15,20-tetrakis-(carboxyethyl-4-pyridyl)-21H,23H-porphine chloride, 5,10,15,20-tetrakis-(carboxyethyl-4-pyridyl)-21H,23H-porphine bromide, 5,10,15,20-tetrakis-(carboxylate-4-pyridyl)-21H,23H-porphine, 2,3,7,8,12,13,17,18-octa-(2-hydroxyethyl)-21H-23H-porphine, 2,3,7,8,12,13,17,18-octa-(2-hydroxyethoxyethyl)-21H-23H-porphine, 2,3,7,8,12,13,17,18-octa-(2-aminoethyl)-21H-23H-porphine, and 2,3,7,8,12,13,17,18-octa-(2-hydroxyethoxypropyl)-21H-23H-porphine.

6. An ink in accordance with claim 1 wherein the absorption spectrum of the dye exhibits strong bands at from between about 380 and about 500 nanometers.

7. An ink in accordance with claim 1 wherein the absorption spectrum of the dye exhibits strong bands at from between about 380 and about 500 nanometers, and weaker bands at from between about 600 and about 800 nanometers.

8. An ink in accordance with claim 1 wherein the dye is present in an amount of about 0.001 to about 1 percent by weight, and the solution contains water in an amount of from about 75 to about 98 percent by weight.

9. An ink in accordance with claim 1 containing a humectant present in the amount of from about 2 to about 50 percent by weight.

10. An ink in accordance with claim 9 wherein the humectant is an aliphatic or aromatic glycol.

11. An ink in accordance with claim 9 wherein the humectant is a glycol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, and mixtures thereof.

12. An ink in accordance with claim 1 with a biocide present in the amount of from about 0.02 to about 0.1 percent by weight.

13. An ink in accordance with claim 1 wherein the dendrimer is a first, second or third generation dendrimer.

14. An ink in accordance with claim 1 wherein the dendrimer is a dendrimer of the first generation with an average diameter of about 10.8 Angstroms, and with 6 terminal amino groups.

15. An ink in accordance with claim 1 wherein the dendrimer is of the third generation with an average diameter of about 22 Angstroms, and with 24 terminal amino groups.

16. An ink in accordance with claim 1 wherein the dye is present in an amount of about 0.001 to about 1 percent by weight, the dendrimer is present in an amount of about 0.2 to about 15 percent by weight, and the solution contains water in an amount of from about 75 to about 98 percent by weight.

17. An ink in accordance with claim 1 wherein the dye is present in an amount of about 0.05 to about 0.5 percent by weight, the dendrimer is present in an amount of from about 0.01 to about 2 percent by weight, and the solution contains water in an amount of from about 96 to about 80 percent by weight.

18. An ink in accordance with claim 1 with a waterfastness of from between about 85 to about 99 percent.