IP Library Granted Patent US 7,365,105
Granted Patent B2
US 7,365,105 · App. 10/986,561 · Granted Apr 29, 2008

Radiation curable ink compositions and applications thereof

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Quick Facts
Patent No.
US 7,365,105
App. No.
10/986,561
Granted
Apr 29, 2008
Kind
B2
Abstract

Radiation curable ink compositions that include a curable component having a functionality that is greater than two, is present in the ink composition in an amount greater than 30 percent by weight, and has a molecular weight in the range of about 400 g/mole to about 10,000 g/mole; a component that has a functionality that is less than or equal to 2; and an initiator component. A solvent component, pigment, a surface tension modifier and other materials also can be included. The radiation curable inks are employed in ink jet printers and are particularly suited for use in printing on large-scale substrates. The printed images described herein have good adhesion to polymeric substrates such as styrene-based, polycarbonates, polyolefins, polyethylene terephthalate glycol ester, acrylic and others.

Claims (56)

1. A radiation curable ink composition for ink jet printing, comprising:

a) a first curable component that is present in the ink composition in an amount greater than 30 weight percent, has a functionality that is greater than 2 and a molecular weight in the range of from about 400 g/mole to about 10,000 g/mole, wherein the first curable component includes any of: (1) a hyperbranched or a dendridic acrylate oligomer; or (2) a polyester tetraacrylate oligomer;

b) a second curable component that has a functionality that is less than or equal to 2; and

c) an initiator component.

2. The radiation curable ink composition of claim 1 , wherein the ink composition is UV curable.

3. The radiation curable ink composition of claim 1 , wherein the first curable component includes ethoxylated trimethylolpropane triacrylate.

4. The radiation curable ink composition of claim 3 , wherein ethoxylated trimethylolpropane triacrylate is present in the radiation curable ink composition in an amount of at least about 16 weight percent.

5. The radiation curable ink composition of claim 4 , wherein ethoxylated trimethylolpropane triacrylate is present in the radiation curable ink composition in an amount in the range of from about 22 to about 31 weight percent.

6. The radiation curable ink composition of claim 1 , wherein the first curable component includes a hyperbranched or dendridic acrylate oligomer that is present in the radiation curable ink composition in an amount of no more than 9 weight percent.

7. The radiation curable ink composition of claim 1 , wherein the first curable component has a viscosity greater than 50 centipoise at 25° Celsius.

8. The radiation curable ink composition of claim 1 , wherein the second curable component includes at least one monofunctional (meth)acrylate compound and at least one difunctional (meth)acrylate compound.

9. The radiation curable ink composition of claim 1 , wherein the second curable component includes ethoxylated (2) neopentylglycol diacrylate, propoxylated (2) neopentylglycol diacrylate, 1,4-cyclohaxanedimethanol diacrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, ethoxylated 1,6-hexanediol diacrylate, propoxylated-1,6-hexanediol diacrylate, dipropylene glycol diacrylate or any combination thereof.

10. The radiation curable ink composition of claim 1 , wherein the second curable component is present in the curable ink composition in an amount of less than about 70 weight percent.

11. The radiation curable ink composition of claim 10 , wherein the second curable component is present in the curable ink composition in an amount in the range of from about 45 to about 51 weight percent.

12. The radiation curable ink composition of claim 1 , wherein the record component has a viscosity that is less than 50 centipoise at 25° centigrade.

13. The radiation curable ink composition of claim 1 , wherein the initiator component includes at least one photoinitiator.

14. The radiation curable ink composition of claim 13 , wherein the initiator component includes bensophenone, bensoin ether, acylphosphine, or any combination thereof.

15. The radiation curable ink composition of claim 1 , wherein the initiator component is present in the curable ink composition in an amount in the range of from about 2 to about 20 weight percent.

16. The radiation curable ink composition of claim 15 , wherein the initiator component is present in the curable ink composition in an amount in the range of from about 7 to about 16 weight percent.

17. The radiation curable ink composition of claim 1 , further including a pigment.

18. The radiation curable ink composition of claim 17 , wherein the pigment is present in the radiation curable ink composition in an amount less than 10 weight percent.

19. The radiation curable ink composition of claim 1 , further comprising a solvent.

20. The radiation curable ink composition of claim 1 , further comprising a surface tension modifier.

21. The radiation curable ink composition of claim 20 , wherein the surface tension modifier is an organosilicon compound.

22. The radiation curable ink composition of claim 21 , wherein the organosilicon compound is a silicone acrylate.

23. The radiation curable ink composition of claim 22 , wherein the silicone acrylate is present in the radiation curable ink composition in an amount of at least 0.01 weight percent.

24. The radiation curable ink composition of claim 1 , wherein the radiation curable ink composition has a viscosity that is less than 25 centipoise at jet temperature.

25. The radiation curable ink composition of claim 24 , wherein the radiation curable ink composition has a viscosity in the range of from 10 to about 13 centipoise at a temperature in the range of from about 40° C. to about 58° C.

26. The radiation curable ink composition of claim 1 , wherein the radiation curable ink composition has a surface tension that is less than 30 dynes/cm 2 .

27. The radiation curable ink composition of claim 26 , wherein the radiation curable ink composition has a surface tension in the range of from about 25.5 to about 26.5 dynes/cm 2 .

28. A method for inkjet printing on a polymer-based substrate, the method comprising:

a) delivering a curable ink composition from an inkjet printer printhead onto the substrate, wherein the ink composition includes:

i. a first curable component that is present in the ink composition in an amount greater than 30 weight percent, has a functionality that is greater than 2 and a molecular weight in the range of from about 400 g/mole to about 10,000 g/mole, wherein the first curable component includes any of: (1) a hyperbranched or a dendridic acrylate oligomer; or (2) a polyester tetraacrylate oligomer;

ii. a second curable component that has a functionality that is less than or equal to 2; and

iii. an initiator component; and

b) exposing the ink composition to ultraviolet radiation, thereby curing the ink composition on said surface.

29. The method of claim 28 , wherein the ultraviolet radiation is provided by a lamp.

30. The method of claim 28 , wherein the curable ink composition is ejected from the printhead at a jet temperature in the range of from about 40° C. to about 58° C.

31. A printed display sign comprising:

a) a polymer-based substrate; and

b) a printed image adhered to said substrate, wherein the printed image is formed by curing an ink composition that includes:

i. a first curable component that is present in the ink composition in an amount greater than 30 weight percent, has a functionality that is greater than 2 and a molecular weight in the range of from about 400 g/mole to about 10,000 g/mole, wherein the first curable component includes any of: (1) a hyperbranched or a dendridic acrylate oligomer; or (2) a polyester tetraacrylate oligomer;

ii. a second curable component that has a functionality that is less than or equal to 2; and

iii. an initiator component, wherein the adhesion of the printed image to said substrate is at least 95 percent when measured by a standard cross-hatched tape test.

32. A printed display sign comprising:

a) a polymer-based substrate; and

b) a printed image adhered to said substrate, wherein the printed image is formed by curing an ink composition that includes:

i. a first curable component that is present in the ink composition in an amount greater than 30 weight percent, has a functionality that is greater than 2 and a molecular weight in the range of from about 400 g/mole to about 10,000 g/mole, wherein the first curable component includes any of: (1) a hyperbranched or a dendridic acrylate oligomer; or (2) a polyester tetraacrylate oligomer;

ii. a second curable component that has a functionality that is less than or equal to 2; and

iii. an initiator component, wherein the printed image has a hardness of at least HB on the pencil hardness scale.

33. A printed display sign comprising:

a) a polymer-based substrate; and

b) a printed image adhered to said substrate, wherein the printed image is formed by curing an ink composition that includes:

ii. a first curable component that is present in the ink composition in an amount greater than 30 weight percent, has a functionality that is greater than 2 and a molecular weight in the range of from about 400 g/mole to about 10,000 g/mole, wherein the first curable component includes: any of (1) a hyperbranched or a dendridic acrylate oligomer, or (2) a polyester tetraacrylate oligomer;

i. a second curable component that has a functionality that is less than or equal to 2; and

iii. an initiator component, wherein the printed image has a water resistance recover of less than 5 minutes.

Assignments (10)
ASSIGNMENT OF SECURITY INTEREST IN PATENTS Recorded Feb 3, 2025
From: ROYAL BANK OF CANADA [RESIGNING COLLATERAL AGENT]
To: GLAS USA LLC [SUCCESSOR COLLATERAL AGENT]
Reel/Frame 070097/0810 →
RELEASE OF PATENT SECURITY INTEREST Recorded Dec 3, 2024
From: CERBERUS BUSINESS FINANCE AGENCY, LLC
To: ELECTRONICS FOR IMAGING, INC.; FIERY, LLC
Reel/Frame 069477/0479 →
SECURITY INTEREST Recorded Mar 12, 2024
From: ELECTRONICS FOR IMAGING, INC.; FIERY, LLC
To: CERBERUS BUSINESS FINANCE AGENCY, LLC
Reel/Frame 066794/0315 →
RELEASE OF SECURITY INTEREST Recorded Mar 11, 2024
From: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS AGENT
To: ELECTRONICS FOR IMAGING, INC.
Reel/Frame 066793/0001 →
SECURITY INTEREST Recorded Jul 23, 2019
From: ELECTRONICS FOR IMAGING, INC.
To: ROYAL BANK OF CANADA
Reel/Frame 049840/0799 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 23, 2019
From: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
To: ELECTRONICS FOR IMAGING, INC.
Reel/Frame 049840/0316 →
SECOND LIEN SECURITY INTEREST IN PATENT RIGHTS Recorded Jul 23, 2019
From: ELECTRONICS FOR IMAGING, INC.
To: DEUTSCHE BANK TRUST COMPANY AMERICAS
Reel/Frame 049841/0115 →
GRANT OF SECURITY INTEREST IN PATENTS Recorded Jan 3, 2019
From: ELECTRONICS FOR IMAGING, INC.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 048002/0135 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2006
From: VUTEK, INCORPORATED
To: ELECTRONICS FOR IMAGING, INC.
Reel/Frame 017429/0165 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2005
From: KIEFER-LIPTAK, LAURA A.
To: VUTEK INCORPORATED
Reel/Frame 015968/0744 →