LOW MIGRATION UV-LED CURABLE INK FORMULATIONS

Abstract

UV-LED ink composition compositions containing a matrix or binder system, one or more colorants, and one or more photo-initiators. In some embodiments, the matrix or binder system is cured using one or more UV-LED sources. In some embodiments, the matrix or binder system contains one or more materials that are polymerized, crosslinked, and/or cured upon exposure to the UV-LED source. This allows the ink composition to be free of any organic solvents. After polymerization and/or crosslinking, the ink is dry. UV-LED ink compositions can be better suited for curing black inks, improve/increase productivity due to its instant on/instant off capability, and produce little or no heat. Such compositions may have environmental benefits as well as the curing process does not produce ozone and requires less exhaust air surrounding the press.

Claims

1. A photocurable ink composition comprising: (a) a matrix comprising one or more photo-curable or photo-polymerizable monomers, oligomers, polymers, or combinations thereof; (b) one or more polymeric diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) photo-initiators; (c) and one or more pigments.

2. The composition of claim 1, wherein the matrix comprises one or more chain extension agents.

3. The composition of claim 2, wherein the chain extension agent comprises one or more difunctional acrylate polymers or copolymers.

4. The composition of claim 1, wherein the one or more difunctional acrylate polymer or copolymer comprises a 1,6-hexane ethoxylate diacrylate.

5. The composition of claim 1, wherein the matrix comprises one or more multifunctional crosslinking agents.

6. The composition of claim 5, wherein the multifunctional crosslinking agent comprises one or more trifunctional acrylate polymers or copolymers.

7. The composition of claim 6, wherein the one or more trifunctional acrylate polymers or copolymers comprises a trimethylolpropane ethoxylate triacrylate.

8. The composition of claim 1, wherein the matrix comprises one or more reactive diluents.

9. The composition of claim 8, wherein the one or more reactive diluents comprises one or more monofunctional acrylate polymers or copolymers.

10. The composition of claim 9, wherein the one or more monofunctional acrylate polymers or copolymers comprises a cyclic trimethylolpropoylacrylate.

11. The composition of claim 1, wherein the matrix comprises one or more monomers, oligomers, polymers, or combinations thereof to improve or enhance surface cure of the matrix.

12. The composition of claim 11, wherein the one or more monomers, oligomers, polymers, or combinations thereof to improve or enhance surface cure of the matrix comprises an amine-modified polyether acrylate.

13. The composition of claim 1, wherein the matrix comprises one or more monomers that provide flexibility, elongation, and/or stretch to the matrix.

14. The composition of claim 13, wherein the one or more monomers comprise a urethane acrylate.

15. The composition of claim 1, wherein the polymeric TPOL is a linear polymer.

16. The composition of claim 15, wherein the linear polymer is an alkylene oxide polymer or copolymer.

17. The composition of claim 16, wherein the alkylene polymer or copolymer is a polyethylene oxide homopolymer or copolymer.

18. The composition of claim 17, wherein the polyethylene oxide polymer is a polyethylene oxide homopolymer.

19. The composition of claim 1, wherein the polymeric TPO is a branched polymer.

20. The composition of claim 19, wherein the branched polymer is a branched alkylene oxide polymer or copolymer.

21. The composition of claim 20, wherein the branched alkylene polymer or copolymer is a branched polyethylene oxide homopolymer or copolymer.

22. The composition of claim 21, wherein the branched polyethylene oxide polymer is a branched polyethylene oxide homopolymer.

23. The composition of claim 1, further comprising one or more non-polymeric diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO) photo-initiators.

24. The composition of claim 1, further comprising a plasticizer.

25. The composition of claim 1, wherein the ink composition is a yellow ink composition, a magenta ink composition, a cyan ink composition, a black ink composition, a light magenta ink composition, a white ink composition, a light cyan ink composition, or combinations thereof.

26. The composition of claim 1, wherein the pigment is at least one of Pigment Blue 1, Pigment Blue 15, Pigment Blue 15:1, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Blue 15:6, Pigment Blue 16, Pigment Blue 17-1, Pigment Blue 22, Pigment Blue 22, Pigment Blue 27, Pigment Blue 28, Pigment Blue 29, Pigment Blue 36, and Pigment Blue 60.

27. The composition of claim 1, wherein the pigment is at least one of Pigment Red 3, Pigment Red 5, Pigment Red 8, Pigment Red 9, Pigment Red 9:8, Pigment Red 19, Pigment Red 22, Pigment Red 31, Pigment Red 38, Pigment Red 43, Pigment Red 48:1, Pigment Red 48:2, Pigment Red 48:3, Pigment Red 48:4, Pigment Red 48:5, Pigment Red 49:1, Pigment Red 53:1, Pigment Red 57:1, Pigment Red 57:2, Pigment Red 58:4, Pigment Red 63:1, Pigment Red 81, Pigment Red 81:1, Pigment Red 81:2, Pigment Red 81:3, Pigment Red 81:4, Pigment Red 88, Pigment Red 104, Pigment Red 108, Pigment Red 112, Pigment Red 122, Pigment Red 123, Pigment Red 144, Pigment Red 146, Pigment Red 149, Pigment Red 166, Pigment Red 168, Pigment Red 169, Pigment Red 170, Pigment Red 177, Pigment Red 178, Pigment Red 179, Pigment Red 184, Pigment Red 185, Pigment Red 207, Pigment Red 208, Pigment Red 216, Pigment Red 224, Pigment Red 226, Pigment Red 257, Pigment Violet 3, Pigment Violet 19, Pigment Violet 23, Pigment Violet 29, Pigment Violet 30, Pigment Violet 37, Pigment Violet 50, Pigment Violet 88, Pigment Orange 13, Pigment Orange 16, Pigment Orange 20, or Pigment Orange 36.

28. The composition of claim 1, wherein the pigment is at least one of Pigment Yellow 55, Pigment Yellow 74, Pigment Yellow 79, Pigment Yellow 93, Pigment Yellow 110, Pigment Yellow 120, Pigment Yellow 128, Pigment Yellow 138C, Pigment Yellow 139, Pigment Yellow 150, Pigment Yellow 151, Pigment Yellow 155, Pigment Yellow 156, Pigment Yellow 175, Pigment Yellow 180, Pigment Yellow 185 and Pigment Yellow 213.

29. The composition of claim 1, wherein the pigment is at least one of Pigment Black 6, Pigment Black 7, Pigment Black 9, lamp or vegetable black, bone or ivory black, and furnace or channel black.

30. An ink set comprising at least a yellow ink composition, a magenta ink composition, a cyan ink composition, and a black ink composition, wherein at least one of the ink compositions comprises the ink composition according to claim 1.

31. The ink set of claim 30, wherein at least two of the ink compositions comprises the ink composition according to claim 1.

32. The ink set of claim 30, wherein at least three of the ink compositions comprises the ink composition according to claim 1.

33. The ink set of claim 30, wherein each of the yellow ink composition, the magenta ink composition, the cyan ink composition, and the black ink composition comprise the ink composition according to claim 1.

Description

EXAMPLES

Example 1: Comparison of White Inks Containing TPO and Polymeric TPOL

[0053] White ink formulations were prepared containing the following compositions:

TABLE-US-00001 TABLE 1 White Ink Formulations (40-50 Microns) White 1 White 2 (Monomeric TPO) (Polymeric TPOL) Material HD(EO)3DA    61%    59% TMP(EO)3TA     5%     5% Lauryl Acrylate     5%     5% White Pigment 19.80% 19.80% TPO (phosphine oxide)     9% Poly TPOL    11% Tego 270 (surfactant)  0.40%  0.40% Tego 450 (surfactant)  0.20%  0.20%

[0054] Residual amounts of monomer and TPO on a polycarbonate substrate were analyzed by gas chromatography-mass spectrometry (GC-MS) and expressed as ppm based on ink weight alone. The results are shown below:

TABLE-US-00002 TABLE 2 Residual Amounts of TPO Residual Monomer Substrate: Polycarbonate by GC-MS (ppm based on ink weight alone) Ink Name Monomer (acrylates) TPO White 1 242 11,800 White 2 614 238

Example 2. Comparison of Cyan Inks Containing Monomeric TPO and Polymeric TPOL

[0055] Cyan ink formulations were prepared containing the following compositions:

TABLE-US-00003 TABLE 3 Cyan Ink Formulations (10 Microns) Ingredient Cyan 2 Cyan 4 M202 M2010 57 57 LR3130 20 20 M3160 M122 0.1 0.1 CN991 Tego glide 450 0.29 0.29 Cyan Pig 9S 1109 9.6 9.6 TPO 8.65 Poly TPOL 9.5 BAPO 2.88 2.9 DETX 1.92 1.92

[0056] Residual amounts of monomer and TPO on polyester textile and polyester/cotton textile were analyzed by gas chromatography-mass spectrometry (GC-MS) and expressed as ppm based on ink weight alone. The results are shown below:

TABLE-US-00004 TABLE 4 Residual Amounts of TPO (ppm) Cyan 2 Cyan 4 Polyester Textile Residual Monomer 643 514 Residual TPO 150 4 Polyester/Cotton Residual Monomer 295 241 Textile Residual TPO 66 −6

Example 3. Comparison of Yellow Inks Containing Monomeric TPO and Polymeric TPOL

[0057] Yellow ink formulations were prepared containing the following compositions:

TABLE-US-00005 TABLE 5 Yellow Ink Formulations Ingredient Yellow 1 Yellow 2 M202 71 70 LR3130 7 7 M3160 M122 5 5 Tego glide 450 0.30 0.30 Magenta Yellow 5.88 5.88 TPO 6 Poly TPOL 7 BAPO 2.9 2.9 Irgastab UV22

[0058] Residual amounts of monomer and TPO on polyester textile and polyester/cotton textile were analyzed by gas chromatography-mass spectrometry (GC-MS) and expressed as ppm based on ink weight alone. The results are shown below:

TABLE-US-00006 TABLE 6 Residual Amounts of TPO (ppm) Yellow 1 Yellow 2 Polyester Textile Residual Monomer 154 143 Residual TPO 20 9 Polyester/Cotton Residual Monomer 131 147 Textile Residual TPO 37 8

Example 4. Comparison of Magenta Inks Containing Monomeric TPO and Polymeric TPOL

[0059] Magenta ink formulations were prepared containing the following compositions:

TABLE-US-00007 TABLE 7 Magenta Ink Formulations Ingredient Magenta 1 Magenta 2 M202 63 62 LR3130 5.5 5.5 M3160 M122 5 5 Tego glide 450 0.30 0.30 Magenta 13.62 13.62 Yellow TPO 7 Poly TPOL 8 BAPO 3 3 Irgastab UV22

[0060] Residual amounts of monomer and TPO on polyester textile and polyester/cotton textile were analyzed by gas chromatography-mass spectrometry (GC-MS) and expressed as ppm based on ink weight alone. The results are shown below:

TABLE-US-00008 TABLE 8 Residual Amounts of TPO (ppm) Magenta 1 Magenta 2 Polyester Textile Residual Monomer 119 122 Residual TPO 19 9 Polyester/Cotton Residual Monomer 139 130 Textile Residual TPO 22 8