Phase change inks

• US 6,372,030 B1
• Filed: 08/03/2000
• Issued: 04/16/2002
• Est. Priority Date: 08/03/2000
• Status: Expired due to Term

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Wong, Raymond W., Breton, Marcel P., Malhotra, Shadi L.
• Primary Examiner(s): Koslow, C. Melissa
• Assistant Examiner(s): Faison, Veronica F.
• Application Number:
  US09/631,602
• Time in Patent Office: 621 Days
• Field of Search: 106/31.32, 106/31.43, 106/31.75, 106/31.29, 106/31.61, 106/31.64, 106/31.92
• US Class Current: 106/31.32
• CPC Class Codes: C09D 11/34 Hot-melt inks

Abstract

Disclosed is an ink composition comprising (a) an ink vehicle selected from 4-(hexadecylamino)benzylamine, N-octanoyl-N-methyl glucamine, octanoic hydrazide, 4-hexadecyl sulfonyl aniline, or mixtures thereof, (b) a conductive complex of (i) an amine compound with (ii) a phosphorus-containing acid or acid salt or a sulfur-containing acid or acid salt, (c) a colorant, (d) an optional amine compound viscosity modifier, (e) an optional antioxidant, and (f) an optional UV absorber.

Claims

1. An ink composition comprising (a) an ink vehicle selected from 4-(hexadecylamino)benzylamine, N-octanoyl-N-methyl glucamine, octanoic hydrazide, 4-hexadecyl sulfonyl aniline, or mixtures thereof, (b) a conductive complex of (i) an amine compound with (ii) a phosphorus-containing acid or acid salt or a sulfur-containing acid or acid salt, (c) a colorant, (d) an optional amine compound viscosity modifier, (e) an optional antioxidant, and (f) an optional UV absorber.

2. An ink composition according to claim 1 wherein the ink vehicle is present in the ink in an amount of at least about 40 percent by weight of the ink, and wherein the ink vehicle is present in the ink in an amount of no more than about 80 percent by weight of the ink.

3. An ink composition according to claim 1 wherein the amine compound is p-methoxyaniline, 3-benzyloxyaniline, 2-nitroaniline, 3-nitroaniline, 4-phenoxyaniline, 3-(1-hydroxyethyl)aniline, 4-cyano aniline, N-methylanilinium trifluoroacetate, N-methylaniline chromium tricarbonyl, 2,5-di-tert-butyl aniline, 2,5-dimethoxyaniline, 3,4-dimethoxy aniline, 5-chloro-2-methoxyaniline, 3,4-dichloroaniline, dibromoaniline, 4-bromo-3-methylaniline, 2-methyl-3-nitroaniline, 2-methyl-5-nitroaniline, 2-methyl-6-nitroaniline, 4-methyl-2-nitroaniline, 4-methyl-3-nitroaniline, 5-methyl-2-nitroaniline, 2-chloro-4-nitroaniline, 2-chloro-5-nitroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline, 5-chloro-2-nitroaniline, N-ethyl-4-nitroaniline, 3,4,5-trimethoxyaniline, 2,3,4-trichloroaniline, 2,4,5-trichloroaniline, 2,4,6-trichloroaniline, 3,4,5-trichloroaniline, 4-chloro-2-methoxy-5-methylaniline, 2,4-dichloro-6-nitroaniline, 4,5-difluoro-2-nitroaniline, 2,4,6-triphenylaniline, N,N-dimethyl-4-nitrosoaniline, N,N-diethyl-4-nitrosoaniline, 2-nitro-5-(propylthio)aniline, N,N-dimethyl-3-nitroaniline, 4,6-dimethyl-2-nitroaniline, 2,3-dimethyl-6-nitroaniline, 2,4,6-tribromo aniline, 2,4,6-tri-tert-butyl-N-methylaniline, 2,3,5,6-tetrachloroaniline, 2-(phenylsulfonyl)aniline, 4-phenylazoaniline, 2-nitro-4-(trifluoromethyl)aniline, 4-nitro-2-(trifluoromethyl)aniline, 4-nitro-3-(trifluoromethyl)aniline, N-((diphenylphosphinyl)methyl)-N-methylaniline, 2,2′

-dithio dianiline, 4,4′

-dithiodianiline, 3,3′

-methylene dianiline, 4,4′

-methylene dianiline, N-methyl-4,4′

-methylene dianiline, 4,4′

-methylene bis(2,6-diethylaniline), 4,4′

-methylene bis(2,6-diisopropyl-N,N-dimethylaniline), 4,4′

-methylene bis (N,N-dimethylaniline), 4,4′

-methylene bis (2,6-dimethylaniline), 4,4′

-methylene bis (3-chloro-2,6-diethylaniline), 3,3′

-(sulfonyl bis(4,1-phenylene))dianiline, 4,4′

-(1 ,3-phenylene diisopropylidene)bisaniline, dodecyl amine, tridecyl amine, 1-tetradecyl amine, hexadecyl amine, octadecyl amine, 1,7-diamino heptane, 1,8 diamino octane, 1,9 diamino nonane, 1,10-diaminodecane, 1,12-diamino dodecane, tribenzyl amine, 2-chloro-4-fluoro-5-methyl aniline, 2,6-dibromo-4-fluoroaniline, S-chloro-2,A-difluoroaniline, 4-bromo-2,3,5,6-tetrafluoroaniline, 2,4,5-trifluoro aniline, 2,4-dibromo-6-fluoroaniline, or mixtures thereof.

4. An ink composition according to claim 1 wherein the conductive complex contains a phosphorus-containing acid which is phenylphosphinic acid, dimethylphosphinic acid, methyl phosphonic acid, or mixtures thereof.

5. An ink composition according to claim 1 wherein the conductive complex contains a sulfur-containing acid which is 2,4-dinitrobenzene sulfonic acid dihydrate, 2-propanesulfonic acid sodium salt monohydrate, p-toluenesulfonic acid monohydrate, hydroxymethane sulfinic acid monosodium salt dihydrate, or mixtures thereof.

6. An ink composition according to claim 1 wherein the conductive complex is present in the ink in an amount of at least about 20 percent by weight of the ink, and wherein the conductive complex is present in the ink in an amount of no more than about 50 percent by weight of the ink.

7. An ink composition according to claim 1 wherein the colorant is a pigment.

8. An ink composition according to claim 1 wherein the colorant is a dye.

9. An ink composition according to claim 1 wherein the colorant is present in the ink in an amount of at least about 1 percent by weight of the ink, and wherein the colorant is present in the ink in an amount of no more than about 15 percent by weight of the ink.

10. An ink composition according to claim 1 containing a viscosity modifier which is p-methoxyaniline, 3-benzyloxyaniline, 2-nitroaniline, 3-nitroaniline, 4-phenoxyaniline, 3-(1-hydroxyethyl)aniline, 4-cyanoaniline, N-methylanilinium trifluoroacetate, N-methylaniline chromium tricarbonyl, 2,5-di-tert-butyl aniline, 2,5-dimethoxyaniline, 3,4-dimethoxyaniline, 5-chloro-2-methoxyaniline, 3,4-dichloroaniline, dibromoaniline, 4-bromo-3-methylaniline, 2-methyl-3-nitroaniline, 2-methyl-5-nitroaniline, 2-methyl-6-nitroaniline, 4-methyl-2-nitroaniline, 4-methyl-3-nitroaniline, 5-methyl-2-nitroaniline, 2-chloro-4-nitroaniline, 2-chloro-5-nitroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline, 5-chloro-2-nitroaniline, N-ethyl-4-nitroaniline, 3,4,5-trimethoxyaniline, 2,3,4-trichloroaniline, 2,4,5-trichloroaniline, 2,4,6-trichloroaniline, 3,4,5-trichloroaniline, 4-chloro-2-methoxy-5-methylaniline, 2,4-dichloro-6-nitroaniline, 4,5-difluoro-2-nitroaniline, 2,4,6-triphenylaniline, N, N-dimethyl-4-nitrosoaniline, N,N-diethyl-4-nitrosoaniline, 2-nitro-5-(propylthio)aniline, N,N-dimethyl-3-nitroaniline, 4,6-dimethyl-2-nitroaniline, 2,3-dimethyl-6-nitroaniline, 2,4,6-tribromo aniline, 2,4,6-tri-tert-butyl-N-methylaniline, 2,3,5,6-tetrachloroaniline, 2-(phenylsulfonyl)aniline, 4-phenylazoaniline, 2-nitro-4-(trifluoromethyl)aniline, 4-nitro-2-(trifluoromethyl)aniline, 4-nitro-3-(trifluoromethyl)aniline, N-((diphenylphosphinyl)methyl)-N-methylaniline, 2,2′

-dithio dianiline, 4,4′

-dithiodianiline, 3,3′

-methylene dianiline, 4,4′

-methylene dianiline, N-methyl-4,4′

-methylene dianiline, 4,4′

-methylene bis(2,6-diethylaniline), 4,4′

-methylene bis(2,6-diisopropyl-N,N-dimethylaniline), 4,4′

-methylene bis (N,N-dimethylaniline), 4,4′

-methylene bis (2,6-dimethylaniline), 4,4′

-methylene bis (3-chloro-2,6-diethylaniline), 3,3′

-(sulfonyl bis(4,1-phenylene))dianiline, 4,4′

-(1 ,3-phenylene diisopropylidene)bisaniline, dodecyl amine, tridecyl amine, 1-tetradecyl amine, hexadecyl amine, octadecyl amine, 1,7-diamino heptane, 1,8 diamino octane, 1,9 diamino nonane, 1,10-diaminodecane, 1,12-diamino dodecane, tribenzyl amine, 2-chloro-4-fluoro-5-methyl aniline, 2,6-dibromo-4-fluoroaniline, 3-chloro-2,4-difluoroaniline, 4-bromo-2,3,5,6-tetrafluoroaniline, 2,4,5-trifluoro aniline, 2,4-dibromo-6-fluoroaniline, or mixtures thereof.

11. An ink composition according to claim 1 containing a viscosity modifier, wherein the viscosity modifier is present in the ink in an amount of at least about 5 percent by weight of the ink, and wherein the viscosity modifier is present in the ink in an amount of no more than about 70 percent by weight of the ink.

12. An ink composition according to claim 1 wherein the ink has a haze value of no more than about 25.

13. An ink composition according to claim 1 wherein the ink has a hardness value of at least about 70 at temperatures of from about 20 to about 25°

C.

14. An ink composition according to claim 1 wherein the ink has a melting point of no lower than about 60°

C., and wherein the ink has a melting point of no higher than about 150°

C.

15. An ink composition according to claim 1 wherein at ink jetting temperatures the ink has a melt viscosity of no more than about 25 centipoise.

16. A process which comprises incorporating into an ink jet printing apparatus an ink composition according to claim 1, melting the ink, and causing droplets of the melted ink to be ejected in an imagewise pattern onto a print substrate.

17. A process according to claim 16 wherein the printing apparatus employs an acoustic ink jet process, wherein droplets of the ink are caused to be ejected in imagewise pattern by acoustic beams.

18. A process according to claim 16 wherein the printing apparatus employs an acoustic ink jet printing process wherein droplets of the ink are formed by acoustic beams without imparting a substantial velocity component toward the print substrate, using a droplet forming force that is sufficient only to form the ink droplets, and wherein the printing process further comprises generating an electric field to exert an electrical force different from the droplet forming force on the ink droplets to move the ink droplets toward the print substrate, and controlling the electrical force exerted on the formed complete ink droplets by the electric field.

19. A process according to claim 16 wherein the printing apparatus employs a piezoelectric ink jet process, wherein droplets of the ink are caused to be ejected in imagewise pattern by oscillations of piezoelectric vibrating elements.

20. A process according to claim 16 wherein the print substrate is heated during the printing process.