Ink compositions

• US 6,066,200 A
• Filed: 04/27/1999
• Issued: 05/23/2000
• Est. Priority Date: 04/27/1999
• 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): Bell, Mark L.
• Assistant Examiner(s): Faison, Veronica F.
• Application Number:
  US09/300,373
• Time in Patent Office: 392 Days
• Field of Search: 106/31.29, 106/31.61, 106/31.58, 106/31.86, 106/31.43, 106/31.75
• US Class Current: 106/31.43
• CPC Class Codes: C09D 11/34 Hot-melt inks

Abstract

An ink composition comprised of (1) a solid urea compound; (2) an alcohol; (3) a lightfastness component; (4) a lightfast antioxidant; and (5) a colorant.

Claims

1. An ink composition comprised of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant, and wherein said ink is substantially free of water.

2. A ink in accordance with claim 1 wherein (1) solid urea compound possesses a melting point of from about 60°

C. to about 120°

C. and an acoustic-loss value of from about 25 to about 80 dB/mm;

(2) the alcohol possesses a melting point of from about 25°

C. to about 90°

C. with an acoustic-loss value of from about 5 to about 40 dB/mm, and which ink possesses an acoustic-loss value of from about 10 to about 80 dB/mm, and a viscosity of from about 1 centipoise to about 20 centipoise at a temperature of from about 125°

C. to about 165°

C.

3. An ink composition in accordance with claim 1 wherein the urea is (1) 1-allyl-2-thiourea;

(2) 1-allyl-3-(2-hydroxyethyl)-2thiourea;

(3) 1-methyl-2-thiourea;

(4) 1-methallyl-3-methyl-2-thiourea;

(5) 1,3-dibutyl-2-thiourea;

(6) 1,1,3,3-tetramethyl-2-thiourea;

(7) N,N'"'"'-di-n-propyl thiourea; and

(8) 1-benzyl-3-methyl-2-thiourea, 1-allyl-2-thiourea, or 1-allyl-3-(2-hydroxyethyl)-2-thiourea.

4. An ink in accordance with claim 1 and which ink generates images with crease values of from about 10 to about 20, haze values of from about 10 to about 25, gloss values of from about 80 to about 85, and which ink possesses an acoustic-loss value of from about 10 to about 80 dB/mm, and a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125°

C. to about 165°

C.

5. An ink composition in accordance with claim 1 wherein alcohol is a cyclic alcohol selected from the group consisting of (1) cycloalkyl alcohols;

(2) 4-tert-butyl cyclohexanol;

(3) 3-aminomethyl-3,5,5-trimethyl cyclohexanol;

(4) 2,2,6,6-tetrachloro cyclohexanol;

(5) cycloalkane methanol;

(6) dicyclohexylmethanol;

(7) 3-cyclohexyl-1-propanol;

(8) 2-amino-3-cyclohexyl-1-propanol;

(9) (S)-2-(tert-butoxy carbonylamino)-3-cyclohexyl-1-propanol;

(10) cycloalkane diol;

(11) cis-3,5-cyclohexa diene-1,2-diol;

(12) ρ

-menthane-3,8-diol;

(13) cyclohexane dimethanol;

(14) 3-cyclohexene-1,1-dimethanol;

(15) 1,3-dioxane-5,5-dimethanol; and

(16) piperidinemethanol.

6. An ink composition in accordance with claim 1 wherein the alcohol is a linear alcohol selected from the group consisting of (1) alkyl alcohols, where the number of carbons in the alkyl chain vary from about 6 to about 22;

and (2) alkane diols where the number of carbons in the alkane chain vary from about 5 to about 14.

7. An ink composition in accordance with claim 1 wherein the alcohol is (3) di(trimethylol propane);

(4) nitromethane trispropanol;

(5) 11-bromo-1-undecanol;

(6) 12-bromo-1-dodecanol;

(7) 2-methyl-2-propyl-1,3-propane diol;

(8) 2,2-diethyl-1,3-propanediol;

(9) (2-(hydroxymethyl)-1,3-propanediol;

(10) 2,2,4-trimethyl-1,3-pentanediol;

(11) 2-butyne-1,4-diol;

(12) (±

)-3,6-dimethyl-4-octyne-3,6-diol;

(13) 3,6-dithia-1,8-octanediol;

or (14) 2,4,7,9-tetramethyl-5-decyne-4,7-diol.

8. An ink composition in accordance with claim 1 wherein the alcohol is amino alcohol selected from the group consisting of (1) 2-(2-aminoethoxy)ethanol;

(2) 2-(2-amino ethylamino) ethanol;

(3) amino-1-propanol;

(4) 2-amino-1-butanol;

(5) 4-amino-1-butanol;

(6) 2-amino-3-methyl-1-butanol;

(7) 5-amino-1-pentanol;

(8) 6-amino-1-hexanol;

(9) DL2-amino-1-hexanol; and

(10) (S)-(-)-N-(tert-butoxycarbonyl) leucinol;

or an aromatic alcohol.

9. An ink composition in accordance with claim 1 wherein the alcohol is selected from the group consisting of benzyl alcohol;

(1) alkyl benzyl alcohols where the number of carbon atoms in the alkyl group vary from 0 to a bout 8;

(2) alkoxy and aryloxy benzyl alcohols where the number of carbons in the alkoxy groups vary from about 1 to about 4;

(3) alkyl alkyl benzyl alcohols where the number of carbons in the alkyl varies from about 1 to about 4;

(4) 2-amino-3-methyl benzyl alcohol;

(5) alkoxy alkoxy benzyl alcohols where the number of carbon atoms in the alkoxy group varies from about 1 to about 4;

(6) 2-hydroxy-3-methoxy benzyl alcohol; and

(7) 3,4,5-trimethoxy benzyl alcohol.

10. An ink composition in accordance with claim 1 wherein the alcohol is selected from the group consisting of phenyl alcohol;

(1) phenylpropanol;

(2) 3-(4-hydroxy phenyl)-1-propanol;

(3) (S)-(-)-1-phenyl-1-butanol;

(4) 2-amino-1-phenyl ethanol;

(5) 3,4-dimethoxy phenethyl alcohol;

(6) 2-phenyl-1,2-propane diol;

(7) 3-phenoxy-1,2-propane diol;

(8) 3-methoxy catechol;

(9) benzhydrol;

(10) methyl benzhydrol;

(11) phenethylalcohol;

(12) 4-methoxy phenethyl alcohol;

(13) 2-hydroxy phenethyl alcohol; and

(14) 2-amino phenethylalcohol.

11. An ink in accordance with claim 1 wherein the lightfastness component is a compound selected from the group consisting of (1) 1,1-(1,2-ethane diyl) bis(3,3,5,5-tetramethyl piperazinone);

(2) 6-ethoxy-1,2-dihydro-2,2,4-trimethyl quinoline;

(3) 2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate;

(4) 2-dodecyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)succinimide; and

(5) 1,2,2,6,6-pentamethyl-4-piperidinyl/β

,β

,β

'"'"',β

'"'"'-tetramethyl-3,9-(2,4,8,10-tetraoxo Spiro (5,5) undecane)diethyl-1,2,3,4-butane tetracarboxylate.

12. An ink in accordance with claim 1 wherein the lightfastness antioxidant compound is selected from the group consisting of (1) antimony dialkyl phosphorodithioate;

(2) molybdenum oxysulfide dithio carbamate;

(3) nickel-bis(o-ethyl) (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate; and

(4) tetra sodium N-(1,2-dicarboxyethyl)-N-octadecyl sulfosuccinamate.

13. An ink in accordance with claim 1 wherein the colorant is selected in an amount of from about 0.5 to about percent by weight.

14. An ink in accordance with claim 1 wherein the colorant is a pigment, or a dye.

15. An ink in accordance with claim 1 wherein the colorant is a pigment of cyan, magenta, yellow, black, or mixtures thereof.

16. An ink in accordance with claim 1 with a viscosity of from about 1 centipoise to about 10 centipoise and an acoustic loss of from about 10 to about 80 dB/mm.

17. A printing process which comprises incorporating into an acoustic ink jet printer the ink of claim 1.

18. A process in accordance with claim 17 wherein said ink generates images with crease values of between about 10 to about 20, haze values of between about 10 to about 25, gloss values between about 80 to about 85, and which ink possesses an acoustic-loss value of from about 10 to about 80 dB/mm, and a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125°

C. to about 165°

C.

19. A process which comprises providing an acoustic ink printer having a pool of the liquid ink of claim 1 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 brought to focus with a finite waist diameter in a focal plane, and causing droplets of the ink to be ejected in imagewise pattern onto a substrate.

20. A process in accordance with claim 19 wherein said ink generates images with crease values of between about 10 to 25, haze values of between about 10 to about 30, gloss values between about 80 about 95, and which ink possesses an acoustic-loss value of from about 10 to about 80 dB/mm, and a viscosity of from about 1 centipoise to about 150 centipoise at a temperature of from about 125°

C. to about 165°

C.

21. An ink comprised of (1) a urea compound;

(2) an optional alcohol;

(3) a lightfastness component;

(4) an antioxidant; and

(5) a colorant, and wherein said ink is substantially free of water.

22. An ink composition comprised of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant, and wherein said ink is substantially free of water, and wherein said urea is (1) 1-allyl-2-thiourea;

(2) 1-allyl-3-(2-hydroxyethyl)-2-thiourea;

(3)1-methyl-2-thiourea;

(4)1-methallyl-3-methyl-2-thiourea;

(5)1,3-dibutyl-2-thiourea;

(6) 1,1,3,3-tetramethyl-2-thiourea;

(7) N,N'"'"'-di-n-propyl thiourea; and

(8)1-benzyl-3-methyl-2-thiourea, 1-allyl-2-thiourea, or 1-allyl-3-(2-hydroxyethyl)-2-thiourea.

27. A printing process which comprises incorporating into an acoustic ink jet printer the ink of claim 22.

23. An ink composition comprised of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant, and wherein said alcohol is a cyclic alcohol selected from the group consisting of (1) cycloalkyl alcohols;

(2) 4-tert-butyl cyclohexanol;

(3) 3-aminomethyl-3,5,5-trimethyl cyclohexanol;

(4) 2,2,6,6-tetrachloro cyclohexanol;

(5) cycloalkane methanol;

(6) dicyclohexylmethanol;

(7) 3-cyclohexyl-1-propanol;

(8) 2-amino-3-cyclohexyl-1-propanol;

(9) (S)-2-(tert-butoxy carbonylamino)-3-cyclohexyl-1-propanol;

(10) cycloalkane diol;

(11) cis-3,5-cyclohexa diene-1,2-diol;

(12) p-menthane-3,8-diol;

(13) cyclohexane dimethanol;

(14) 3-cyclohexene-1,1-dimethanol;

(15) 1,3-dioxane-5,5-dimethanol; and

(16) piperidinemethanol.

24. An ink composition comprised of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant, and wherein said alcohol is a cyclic alcohol selected from the group consisting of (3) di(trimethylol propane);

(4) nitromethane trispropanol;

(5) 11-bromo-1-undecanol;

(6) 12-bromo-1-dodecanol;

(7) 2-methyl-2-propyl-1,3-propane diol;

(8) 2,2-diethyl-1,3-propanediol;

(9) (2-(hydroxymethyl)-1,3-propanediol;

(10) 2,2,4-trimethyl-1,3-pentanediol;

(11) 2-butyne-1,4-diol;

(12) (±

)-3,6-dimethyl-4-octyne-3,6-diol;

(13) 3,6-dithia-1,8-octanediol;

or (14) 2,4,7,9-tetramethyl-5-decyne-4,7-diol.

25. An ink composition comprised of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant, and wherein said alcohol is a cyclic alcohol selected from the group consisting of (1) 2-(2-aminoethoxy)ethanol;

(2) 2-(2-amino ethylamino) ethanol;

(3) amino-1-propanol;

(4) 2-amino-1-butanol;

(5) 4-amino-1-butanol;

(6) 2-amino-3-methyl-1-butanol;

(7) 5-amino-1-pentanol;

(8) 6-amino-1-hexanol;

(9) DL-2-amino-1-hexanol; and

(10) (S)-(-)-N-(tert-butoxycarbonyl) leucinol;

or an aromatic alcohol.

26. An ink composition comprised of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant, and wherein said alcohol is a cyclic alcohol selected from the group consisting of phenyl alcohol;

(1) phenylpropanol;

(2) 3-(4-hydroxy phenyl)-1-propanol;

(3) (S)-(-)-1-phenyl-1-butanol;

(4) 2-amino-1-phenyl ethanol;

(5) 3,4-dimethoxy phenethyl alcohol;

(6) 2-phenyl-1,2-propane diol;

(7) 3-phenoxy-1,2-propane diol;

(8) 3-methoxy catechol;

(9) benzhydrol;

(10) methyl benzhydrol;

(11) phenethylalcohol;

(12) 4-methoxy phenethyl alcohol;

(13) 2-hydroxy phenethyl alcohol; and

(14) 2-amino phenethylalcohol.

28. A process which comprises providing an acoustic ink printer having a pool of the liquid ink of (1) a urea compound;

(2) an alcohol;

(3) a lightfastness component;

(4) a lightfast antioxidant; and

(5) a colorant 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 brought to focus with a finite waist diameter in a focal plane, and causing droplets of the ink to be ejected in imagewise pattern onto a substrate.