Ink compositions

• US 5,688,312 A
• Filed: 03/29/1996
• Issued: 11/18/1997
• Est. Priority Date: 03/29/1996
• Status: Expired due to Term

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Sacripante, Guerino G., Drappel, Stephan V., Paine, Anthony J., Kovacs, Gregory J., Pontes, Fatima M.
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US08/624,154
• Time in Patent Office: 599 Days
• Field of Search: 106/20 R, 106/22 H, 106/23 H, 106/20 D, 106/22 A, 106/23 A, 106/31.49, 106/31.29, 106/31.78, 106/31.61
• US Class Current: 106/31.49
• CPC Class Codes: C09D 11/34 Hot-melt inks

Abstract

An ink composition comprised of a colorant and an imide or bisimide with a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125° C. to about 180° C., and which imide or bisimide is of the Formulas I or II, respectively: ##STR1## wherein R is a hydrocarbon of from about 2 to about 50 carbon atoms; R'"'"' is an alkylene hydrocarbon or a polyalkyleneoxide, each with from about 2 to about 30 carbon atoms; and X is an arylene of from 6 to about 24 carbon atoms, or an alkylene of from about 2 to about 10 carbon atoms.

Claims

1. An ink composition comprised of a colorant and an imide or bisimide and which ink possesses a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125°

C. to about 180°

C., and which imide or bisimide is of the Formulas I or II, respectively;

##STR5## wherein R is a hydrocarbon of from about 2 to about 50 carbon atoms;

R'"'"' is an alkylene hydrocarbon or a polyalkyleneoxide, each with from about 2 to about 30 carbon atoms; and

X is an arylene of from 6 to about 24 carbon atoms, or an alkylene of from about 2 to about 10 carbon atoms, and wherein said ink is a solid at room temperature, about 20°

C. to about 40°

C.

2. An ink composition in accordance with claim 1 wherein the imide or bisimide possesses a molecular weight, M_w, of from about 200 to about 2,000 grams per mole.

3. An ink composition in accordance with claim 1 wherein the colorant is a pigment or dye present in said ink in an amount of from about 0.01 to about 10 percent by weight.

4. An ink composition in accordance with claim 1 wherein said imide is N'"'"'-methylphthalimide, N'"'"'-ethylphthalimide, N'"'"'-propylphthalimide, N'"'"'-butylphthalimide, N'"'"'-hexylphthalimide, N'"'"'-heptylphthalimide, N'"'"'-octylphthalimide, N'"'"'-decylphthalimide, N'"'"'-dodecylphthalimide, N'"'"'-stearylphthalimide, N'"'"'-methylsuccinimide, N'"'"'-ethylsuccinimide, N'"'"'-propylsuccinimide, N'"'"'-butylsuccinimide, N'"'"'-hexylsuccinimide, N'"'"'-heptylsuccinimide, N'"'"'-octylsuccinimide, N'"'"'-decylsuccinimide, N'"'"'-dodecylsuccinimide, N'"'"'-stearylsuccinimide, N'"'"'-methyl-2-octadecen-succinimide, N'"'"'-ethyl-2-octadecen-succinimide, N'"'"'-propyl-2-octadecen-succinimide, N'"'"'-butyl-2-octadecen-succinimide, N'"'"'-hexyl-2-octadecen-succinimide, N'"'"'-heptyl-2-octadecen-succinimide, N'"'"'-octyl-2-octadecene-succinimide, N'"'"'-decyl-2-octadecene-succinimide, N'"'"'-dodecyl-2 -octadecene-succinimide, N'"'"'-stearyl-2 -octadecene-succinimide, N'"'"'-(ethyleneoxyethyleneoxymethane)-phthalimide, N'"'"'-(ethyleneoxyethyleneoxyethyleneoxymethane)-phthalimide, N'"'"'-(ethyleneoxyethyleneoxyethyleneoxyethyleneoxymethane)-phthalimide, N'"'"'-(propyleneoxypropyleneoxymethane)-phthalimide, N'"'"'-(propyleneoxypropyleneoxypropyleneoxymethane)-phthalimide, or N'"'"'-(propyleneoxypropyleneoxypropyleneoxypropyleneoxymethane)-phthalimide;

and wherein said imide is present in an effective amount of from about 85 to about 97 percent by weight of the ink composition.

5. An ink composition in accordance with claim 1 wherein said bisimide is N,N'"'"'-methylene bis-phthalimide, N,N'"'"'-ethylene bis-phthalimide, N,N'"'"'-propylene bis-phthalimide, N,N'"'"'-butylene bis-phthalimide, N,N'"'"'-hexylene bis-phthalimide, N,N'"'"'-heptylene bis-phthalimide, N,N'"'"'-octylene bis-phthalimide, N,N'"'"'-decylene bis-phthalimide, N,N'"'"'-dodecylene bis-phthalimide, N,N'"'"'-stearylene bis-phthalimide, N,N'"'"'-methylene bis-succinimide, N,N'"'"'-ethylene bis-succinimide, N,N'"'"'-propylene bis-succinimide, N,N'"'"'-butylene bis-succinimide, N,N'"'"'-hexylene bis-succinimide, N,N'"'"'-heptylene bis-succinimide, N,N'"'"'-octylene bis-succinimide, N,N'"'"'-decylene bis-succinimide, N,N'"'"'-dodecylene bis-succinimide, N,N'"'"'-stearylene bis-succinimide, N,N'"'"'-methylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-ethylene bis(2,2'"'"'-octadecensuccinimide), N,N'"'"'opropylylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-butylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-hexylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-heptylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-octylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-decylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-dodecylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-stearylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-(ethyleneoxyethyleneoxyethylene)-bis-phthalimide, N,N'"'"'-(ethyleneoxyethyleneoxyethyleneoxyethylene)-bis-phthalimide, N,N'"'"'-(ethyleneoxyethyleneoxyethyleneoxyethyleneoxyethylene)-bis-phthalimide, N,N'"'"'-(propyleneoxypropyleneoxy-propylene)-bis-phthalimide, N,N'"'"'-(propyleneoxypropyleneoxypropyleneoxypropylene)-bis-phthalimide, or N,N'"'"'-(propyleneoxypropyleneoxypropyleneoxypropyleneoxyethylene)-bis-phthalimide;

and wherein said bisimide is present in an effective amount of from about 85 to about 97 percent by weight of the ink composition.

6. An ink composition in accordance with claim 1 wherein said colorant is a dye present in an amount of from about 0.05 to about 20 weight percent.

7. An ink composition in accordance with claim 1 wherein said colorant is a dye present in an amount of from about 1 to about 10 weight percent.

8. An ink composition in accordance with claim 1 wherein said colorant is cyan, magenta, yellow, blue, green, brown, black, or mixtures thereof.

9. An ink composition in accordance with claim 1 wherein said imide or bisimide is present in an amount of from about 60 to about 99 weight percent.

10. An ink composition in accordance with claim 1 wherein said imide or bisimide is present in an amount of from about 80 to about 95 weight percent.

15. An ink composition in accordance with claim 1 wherein the imide is N'"'"'-stearylsuccinimide, N'"'"'-methyl-2-octadecen-succinimide, or N'"'"'-stearylphthalimide.

16. An ink composition in accordance with claim 1 wherein the bisimide is N,N'"'"'-(propyleneoxypropyleneoxypropyleneoxypropylene-oxyethylene)-bis-phthalimide, N,N'"'"'-(ethyleneoxyethyleneoxyethylene)-bis-phthalimide, or N,N'"'"'-dodecylene bis-phthalimide.

17. An ink composition in accordance with claim 1 wherein the viscosity is from about 1 centipoise to about 6 centipoise at a temperature of from about 140°

C. to about 160°

C.

18. An ink composition in accordance with claim 1 wherein R is ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, hexadecyl, octadecyl, stearyl, lauryl, 2'"'"'-methylpentyl, ethyleneoxyethyleneoxy-methane, ethyleneoxyethyleneoxyethylene-methane, or ethyleneoxyethyleneoxyethyleneoxyethylene-methane;

R'"'"' is ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, hexadecylene, octadecylene, stearylene, laurylene, 2'"'"'-methylpentylene, ethyleneoxyethyleneoxyethylene, ethyleneoxyethylene-oxyethylene, ethyleneoxyethyleneoxyethyleneoxyethylene, ethyleneoxyethyleneoxyethyleneoxyethyleneoxyethylene, propylene-oxypropylene-oxypropylene, propyleneoxypropylene-oxypropyleneoxy-propylene, propyleneoxypropyleneoxypropyleneoxypropylene-oxy-propylene, poly(oxypropylene); and

X is phenylene, methylphenylene, benzylene, ethylene, 2'"'"'-methyl-ethylene, 2-ethyl-ethylene, 2-stearyl-ethylene, or 2-octadecenyl-ethylene.

19. An ink composition in accordance with claim 1 wherein R is stearyl or dodecyl, R'"'"' is propyleneoxypropylene-oxypropyleneoxypropylene propylene or poly(oxypropylene), and X is phenylene or ethylene.

11. A process which comprises (a) providing an acoustic ink printer having a pool of liquid ink with a free surface, and a printhead including at least one droplet ejector for radiating the free surface of said ink with focused acoustic radiation to eject individual droplets of ink therefrom on demand, said radiation being directed to focus with a finite waist diameter in a focal plane, said ink comprising a colorant and an imide and which ink possesses a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125°

C. to about 165°

C., and which amide I is of the formula ##STR6## wherein R is alkyl of from about 2 to about 50 carbon atoms; and

X is an alkylene or an arylene; and

wherein said imide is N'"'"'-methylphthalimide, N'"'"'-ethylphthalimide, N'"'"'-propylphthalimide, N'"'"'-butylphthalimide, N'"'"'-hexylphthalimide, N'"'"'-heptylphthalimide, N'"'"'-octylphthalimide, N'"'"'-decylphthalimide, N'"'"'-dodecylphthalimide, N'"'"'-stearylphthalimide, N'"'"'-methylsuccinimide, N'"'"'-ethylsuccinimide, N'"'"'-propylsuccinimide, N'"'"'-butylsuccinimide, N'"'"'-hexylsuccinimide, N'"'"'-heptylsuccinimide, N'"'"'-octylsuccinimide, N'"'"'-decylsuccinimide, N'"'"'-dodecylsuccinimide, N'"'"'-stearylsuccinimide, N'"'"'-methyl-2-octadecen-succinimide, N'"'"'-ethyl-2-octadecen-succinimide, N'"'"'-propyl-2-octadecen-succinimide, N'"'"'-butyl-2-octadecen-succinimide, N'"'"'-hexyl-2-octadecen-succinimide, N'"'"'-heptyl-2-octadecen-succinimide, N'"'"'-octyl-2-octadecene-succinimide, N'"'"'-decyl-2-octadecene-succinimide, N'"'"'-dodecyl-2-octadecene-succinimide, N'"'"'-stearyl-2-octadecene-succinimide, N'"'"'-(ethyleneoxyethyleneoxymethane)-phthalimide, N'"'"'-(ethyleneoxyethyleneoxyethyleneoxymethane)-phthalimide, N'"'"'-(ethyleneoxyethyleneoxyethyleneoxyethyleneoxymethane)-phthalimide, N'"'"'-(propyleneoxypropyleneoxymethane)-phthalimide, N'"'"'-(propyleneoxypropyleneoxypropyleneoxymethane)-phthalimide, or N'"'"'-(propyleneoxypropyleneoxypropyleneoxypropyleneoxymethane)-phthalimide; and

(b) causing droplets of said ink to be ejected onto a recording sheet in an imagewise pattern at a temperature of from about 120°

C. to about 165°

C.

13. A process in accordance with claim 11 wherein said colorant is a dye present in said ink in an amount of from about 0.05 to about 4 percent by weight.

12. A process which comprises (a) providing an acoustic ink printer having a pool of liquid ink with a free surface, and a printhead including at least one droplet ejector for radiating the free surface of said ink with focused acoustic radiation to eject individual droplets of ink therefrom on demand, said radiation being directed to focus with a finite waist diameter in a focal plane, said ink comprising a colorant and a bisimide and which ink possesses a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125°

C. to about 165°

C., and bisamide is of the formula II ##STR7## wherein R'"'"' is an alkylene or polyalkyleneoxide, each with from about 2 to about 30 carbon atoms; and

X is an alkylene or an arylene; and

wherein said bisimide is N,N'"'"'-methylene bis-phthalimide, N,N'"'"'-ethylene bis-phthalimide, N,N'"'"'-propylene bis-phthalimide, N,N'"'"'-butylene bis-phthalimide, N,N'"'"'-hexylene bis-phthalimide, N,N'"'"'-heptylene bis-phthalimide, N,N'"'"'-octylene bis-phthalimide, N,N'"'"'-decylene bis-phthalimide, N,N'"'"'-dodecylene bis-phthalimide, N,N'"'"'-stearylene bis-phthalimide, N,N'"'"'-methylene bis-succinimide, N,N'"'"'-ethylene bis-succinimide, N,N'"'"'-propylene bis-succinimide, N,N'"'"'-butylene bis-succinimide, N,N'"'"'-hexylene bis-succinimide, N,N'"'"'-heptylene bis-succinimide, N,N'"'"'-octylene bis-succinimide, N,N'"'"'-decylene bis-succinimide, N,N'"'"'-dodecylene bis-succinimide, N,N'"'"'-stearylene bis-succinimide, N,N'"'"'-methylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-ethylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-propylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-butylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-hexylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-heptylene bis(2,2'"'"'-octadecen-succinimide), N,N'"'"'-octylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-decylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-dodecylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-stearylene bis(2,2'"'"'-octadecene-succinimide), N,N'"'"'-(ethyleneoxyethyleneoxyethylene)-bis-phthalimide, N,N'"'"'-(ethyleneoxyethyleneoxyethylene-oxyethylene)-bis-phthalimide, N,N'"'"'-(ethyleneoxyethyleneoxyethyleneoxyethylene-oxyethylene)-bis-phthalimide, N,N'"'"'-(propyleneoxypropyleneoxy-propylene)-bis-phthalimide, N,N'"'"'-(propyleneoxypropyleneoxypropylene-oxypropylene)-bis-phthalimide, or N,N'"'"'-(propyleneoxypropyleneoxy-propyleneoxypropyleneoxyethylene)-bis-phthalimide, and (b) causing droplets of said ink to be ejected onto a recording sheet in an imagewise pattern at a temperature of from about 120°

C. to about 165°

C.

14. A process in accordance with claim 12 wherein said colorant is a dye present in said ink in an amount of from about 0.05 to about 4 percent by weight.

20. An ink composition comprised of a colorant and a bisimide and which ink possesses a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125°

C. to about 165°

C., and which bisimide is of the following formula ##STR8## wherein R'"'"' is an alkylene hydrocarbon with from about 2 to about 30 carbon atoms, or a polyalkyleneoxide with from about 2 to about 30 carbon atoms; and

X is an arylene of from about 6 to about 24 carbon atoms, or an alkylene of from about 2 to about 10 carbon atoms.