UV curable ink compositions

• US 20050176841A1
• Filed: 12/30/2004
• Published: 08/11/2005
• Est. Priority Date: 12/30/2003
• Status: Abandoned Application

• Current Assignee: Roy C. Krohn
• Original Assignee: Allied PhotoChemical, Inc.
• Inventors: Krohn, Roy C.
• Application Number:
  US11/027,329
• Publication Number:
  US 20050176841A1
• Time in Patent Office: Days
• US Class Current: 522/81
• CPC Class Codes: C09D 11/101 Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing

Abstract

A UV curable ink composition that comprises a ultraviolet light curable ink composition comprising at least one acrylated oligomer, a pigment, and a photoinitiator is provided. The ink composition of the present invention has a viscosity from about 300 centipoise at 25° C. to about 10000 centipoise at 25° C. In one variation the at least one acrylated oligomer includes an aliphatic acrylated urethane oligomer and an epoxy oligomer. In another variation the ink composition includes an acrylic oligomer.

Claims

1. An ultraviolet (UV) curable ink composition comprising:

a photocurable organic composition comprising at least one acrylated oligomer or an acrylic oligomer;

an optional pigment; and

a photoinitiator

wherein the ultraviolet curable ink composition has a viscosity from about 300 centipoise at 25°

C. to about 10000 centipoise at 25°

C.

2. The ink composition of claim 1 wherein the photocurable organic composition includes at least one acrylated oligomer selected from the group consisting of an acrylated epoxy oligomer, an acrylated polyester oligomer, acrylated silicone oligomer, acrylated acrylic oligomer, acrylated urethane oligomer, an acrylated melamine oligomer, and mixtures thereof.

3. The ink composition of claim 1 wherein the at least one acrylated oligomer comprises an aliphatic acrylated urethane oligomer and an acrylated epoxy oligomer wherein the aliphatic acrylated urethane oligomer and the acrylated epoxy oligomer are present in an amount such that the ink composition has has a viscosity from about 2500 centipoise at 25°

C. to about 7000 centipoise at 25°

C.

4. The ink composition of claim 3 wherein the acrylated epoxy oligomer is selected from the group consisting of:

novolac epoxy acrylate diluted 20% by weight with tripropylene glycol diacrylate;

difunctional bisphenol based epoxy acrylate; and

mixtures thereof.

5. The ink composition of claim 3, wherein the aliphatic acrylated urethane oligomer is selected from the group consisting of:

a) aliphatic urethane diacrylate diluted 10% by weight with 1,6-hexanediol diacrylate;

b) aliphatic urethane triacrylate diluted 15% by weight with 1,6-hexanediol diacrylate);

c) aliphatic urethane diacrylate blended with 20% by weight tripropylene glycol diacrylate;

d) aliphatic urethane diacrylate blended with 25% by weight ethoxylated trimethylol propane triacrylate;

e) aliphatic urethane diacrylate blended with 19% by weight 2(2-ethoxyethoxy)ethyl acrylate;

f) aliphatic urethane diacrylate blended with 20% by weight tripropylene glycol diacrylate;

g) aliphatic urethane diacrylate blended with 20% by weight tripropylene glycol diacrylate;

h) aliphatic urethane diacrylate blended with 25% by weight tripropylene glycol diacrylate;

i) aliphatic urethane diacrylate; and

j) mixtures thereof.

6. The ultraviolet curable ink composition of claim 3 wherein the photocurable organic composition comprises:

an ethylenically unsaturated monomer of the formula;

CH₂═

CR₁—

COO—

R₂

wherein R₁ is hydrogen or lower alkyl and R₂ is dicyclopentenyl oxyethyl, cyclohexyl, 3,3,5-trimethyl cyclohexyl, phenyl, benzyl, naphthyl, isobornyl, or mixtures thereof;

aliphatic acrylated oligomer; and

an epoxy acrylated oligomer;

wherein the ethylenically unsaturated monomer is present in an amount such that the ink composition has a viscosity between 1000 centipoise at 25°

C. and 10,000 centipoise at 25°

C.

7. The ink composition of claim 6 wherein the ethylenically unsaturated monomer is selected from the group consisting of isobornyl acrylate, isobornyl methacrylate, and mixtures thereof.

8. The ink composition of claim 7 wherein:

the aliphatic acrylated urethane oligomer is present in an amount from about 5% to about 95% of the total weight of the ink composition;

the acrylated epoxy oligomer is present in an amount from about 1% to about 30% of the total weight of the ink composition;

the pigment is present in an amount from about 0.1% to about 50% of the total weight of the ink composition;

the ethylenically unsaturated monomer is present in an amount from about 0.1% to about 60% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 1% to about 15% of the total weight of the ink composition.

9. The ink composition of claim 7 wherein:

the aliphatic acrylated urethane oligomer is present in an amount from about 10% to about 50% of the total weight of the ink composition;

the acrylated epoxy oligomer is present in an amount from about 5% to about 25% of the total weight of the ink composition;

the pigment is present in an amount from about 10% to about 25% of the total weight of the ink composition;

the ethylenically unsaturated monomer is present in an amount from about 20% to about 40% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 4% to about 12% of the total weight of the ink composition.

10. The ink composition of claim 3 further comprising a flow promoting agent in an amount from about 0.1% to about 10% of the total weight of the ink composition.

11. The ink composition of claim 3 further comprising an adhesion promoter in an amount from about 1% to about 7% of the total weight of the ink composition.

12. The ink composition of claim 1 where the photocurable organic combination includes an acrylic oligomer comprising a polymeric ester resin diluted with a monomer;

wherein the ultraviolet curable clear ink composition has a viscosity from about 300 centipoise at 25°

C. to about 900 centipoise at 25°

C.

13. The ink composition of claim 12 wherein:

the polymeric ester resin diluted with a monomer is present in an amount from about 75% to about 98% of the total weight of the ink composition;

the pigment is present in an amount from about 0.1% to about 40% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 1% to about 15% of the total weight of the ink composition.

14. The ink composition of claim 12 wherein:

the polymeric ester resin diluted with a monomer is present in an amount from about 75% to about 85% of the total weight of the ink composition;

the pigment is present in an amount from about 1% to about 20% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 4% to about 12% of the total weight of the ink composition.

15. An ultraviolet (UV) curable ink composition comprising:

an acrylic oligomer comprising a polymeric ester resin diluted with a monomer;

an optional pigment; and

a photoinitiator

wherein the ultraviolet curable ink composition has a viscosity from about 300 centipoise at 25°

C. to about 900 centipoise at 25°

C.

16. The ink composition of claim 15 wherein:

the polymeric ester resin diluted with a monomer is present in an amount from about 75% to about 98% of the total weight of the ink composition;

the pigment is present in an amount from about 0.1% to about 40% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 1% to about 15% of the total weight of the ink composition.

17. The ink composition of claim 15 wherein:

the polymeric ester resin diluted with a monomer is present in an amount from about 75% to about 85% of the total weight of the ink composition;

the pigment is present in an amount from about 1% to about 20% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 4% to about 12% of the total weight of the ink composition.

18. A method for coating a substrate with a photocurable ink composition, the method comprising:

applying the ink composition to the substrate, wherein the ink composition includes;

a photocurable organic composition comprising at least one acrylated oligomer;

a pigment; and

a photoinitiator

wherein ultraviolet curable ink composition has a viscosity from about 300 centipoise at 25°

C. to about 10000 centipoise at 25°

C.; and

illuminating the ink composition with a UV light sufficient to cause the ink composition to be incorporated into the ink coating by the time the composition is cured.

19. The method of claim 18, wherein the method of applying the ink composition is spraying.

20. The method of claim 18, wherein the method of applying the ink composition is screen printing.

21. The method of claim 18, wherein the method of applying the ink composition is dipping the substrate into the composition sufficiently to cause the composition to uniformly coat the substrate.

22. The method of claim 18, wherein the method of applying the ink composition is brushing.

23. The method of claim 18, wherein the method of applying the ink composition is selectively depositing to the substrate at predetermined locations.

24. The method of claim 18 wherein the acrylated oligomer is selected from the group consisting of acrylated epoxies, acrylated polyesters, acrylated silicones, acrylated acrylics, acrylated urethanes, acrylated melamines, and mixtures thereof.

25. The method of claim 18 wherein the at least one acrylated oligomer is a combination of an aliphatic acrylated urethane oligomer and an acylated epoxy oligomer.

26. The method of claim 25 wherein the acrylated epoxy oligomer is selected from the group consisting of:

novolac epoxy acrylate diluted 20% by weight with tripropylene glycol diacrylate;

difunctional bisphenol based epoxy acrylate; and

mixtures thereof.

27. The method of claim 25 wherein the aliphatic acrylated urethane oligomer is selected from the group consisting of:

a) aliphatic urethane diacrylate diluted 10% by weight with 1,6-hexanediol diacrylate;

b) aliphatic urethane triacrylate diluted 15% by weight with 1,6-hexanediol diacrylate);

c) aliphatic urethane diacrylate blended with 20% by weight tripropylene glycol diacrylate;

d) aliphatic urethane diacrylate blended with 25% by weight ethoxylated trimethylol propane triacrylate;

e) aliphatic urethane diacrylate blended with 19% by weight 2(2-ethoxyethoxy)ethyl acrylate;

f) aliphatic urethane diacrylate blended with 20% by weight tripropylene glycol diacrylate;

g) aliphatic urethane diacrylate blended with 20% by weight tripropylene glycol diacrylate;

h) aliphatic urethane diacrylate blended with 25% by weight tripropylene glycol diacrylate;

i) aliphatic urethane diacrylate; and

j) mixtures thereof.

28. The method of claim 25 wherein the photocurable organic composition comprises:

an ethylenically unsaturated monomer of the formula;

CH₂═

CR₁—

COO—

R₂

wherein R₁ is hydrogen or lower alkyl and R₂ is dicyclopentenyl oxyethyl, cyclohexyl, 3,3,5-trimethyl cyclohexyl, phenyl, benzyl, naphthyl, isobornyl, or mixtures thereof;

aliphatic acrylated oligomer; and

an epoxy acrylated oligomer;

wherein the ethylenically unsaturated monomer is present in an amount such that the ink composition has a viscosity between 1000 centipoise at 25°

C. and 10,000 centipoise at 25°

C.

29. The method of claim 28 wherein the ethylenically unsaturated monomer is selected from the group consisting of isobornyl acrylate, isobornyl methacrylate, and mixtures thereof.

30. The method of claim 26 wherein:

the aliphatic acrylated urethane oligomer is present in an amount from about 5% to about 95% of the total weight of the ink composition;

the acrylated epoxy oligomer is present in an amount from about 1% to about 30% of the total weight of the ink composition;

the pigment is present in an amount from about 0.1% to about 50% of the total weight of the ink composition;

the ethylenically unsaturated monomer is present in an amount from about 0.1% to about 60% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 1% to about 15% of the total weight of the ink composition.

31. The method of claim 26 wherein:

the aliphatic acrylated urethane oligomer is present in an amount from about 10% to about 50% of the total weight of the ink composition;

the acrylated epoxy oligomer is present in an amount from about 5% to about 25% of the total weight of the ink composition;

the pigment is present in an amount from about 10% to about 25% of the total weight of the ink composition;

the ethylenically unsaturated monomer is present in an amount from about 20% to about 40% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 4% to about 12% of the total weight of the ink composition.

32. The method of claim 25 further comprising a flow promoting agent in an amount from about 1% to about 10% of the total weight of the ink composition.

33. The method of claim 25 further comprising an adhesion promoter in an amount from about 1% to about 7% of the total weight of the ink composition.

34. The method of claim 18 where the photocurable organic combination is a polymeric ester resin diluted with a monomer wherein the ultraviolet curable clear ink composition has a viscosity from about 300 centipoise at 25°

C. to about 900 centipoise at 25°

C.

35. The method of claim 34 wherein:

the polymeric ester resin diluted with a monomer is present in an amount from about 75% to about 98% of the total weight of the ink composition;

the pigment is present in an amount from about 0.1% to about 40% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 1% to about 15% of the total weight of the ink composition.

36. The method of claim 34 wherein:

the polymeric ester resin diluted with a monomer is present in an amount from about 75% to about 85% of the total weight of the ink composition;

the pigment is present in an amount from about 1% to about 20% of the total weight of the ink composition; and

the photoinitiator is present in an amount from about 4% to about 12% of the total weight of the ink composition.