CA2425945A1 - Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications - Google Patents

Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications Download PDF

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Publication number
CA2425945A1
CA2425945A1 CA002425945A CA2425945A CA2425945A1 CA 2425945 A1 CA2425945 A1 CA 2425945A1 CA 002425945 A CA002425945 A CA 002425945A CA 2425945 A CA2425945 A CA 2425945A CA 2425945 A1 CA2425945 A1 CA 2425945A1
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CA
Canada
Prior art keywords
composition
radiation curable
monomer
ink
oligo
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Granted
Application number
CA002425945A
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French (fr)
Other versions
CA2425945C (en
Inventor
Jennifer L. Lee
Ronald K. Thery
Caroline M. Ylitalo
Richard L. Severance
Dong Wu
Bruce A. Nerad
Verna J. Lemire
James G. Carlson
William J. Hunt
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3M Innovative Properties Co
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Individual
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Publication of CA2425945A1 publication Critical patent/CA2425945A1/en
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Publication of CA2425945C publication Critical patent/CA2425945C/en
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Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing

Abstract

Low viscosity, radiation curable fluid formulations that can be used advantageously as radiation curable, inks. The formulations are easily prepared for use in ink jet systems. The viscosity of the compositions is low enough so that conventional solvent is not required in order to satisfy the requisite low ink jet viscosity specifications. After curing, the compositions form durable, weatherable, abrasion resistant, printed images on a wide variety of porous and nonporous substrates. The formulations are very suitable for outdoor printing applications, especially for printing outdoor graphics onto a variety of surfaces, including vinyl or other polymer films commonly used for signage, retroreflective signage or other retroreflective items.

Claims (63)

1. An ink jettable, radiation curable ink jet ink composition, comprising:
(a) an oligo/resin component;
(b) a radiation curable, reactive diluent comprising (i) 0.1 to 50 weight percent of an adhesion promoting, radiation curable component comprising one or more heterocyclic, radiation curable monomer and/or an alkoxylated monomer comprising pendant alkoxylated functionality and no main chain alkoxylated functionality and (ii) no more than about 10 weight percent of an optional alkoxylated, radiation curable monomer comprising main-chain alkoxylated functionality.
2. The ink composition of claim 1, wherein the oligo/resin component is aliphatic.
3. The ink composition of claim 1, wherein the oligo/resin component comprises an oligo/resin selected from the group consisting of an aliphatic polyester oligo/resin, an aliphatic polyurethane oligo/resin, and an aliphatic acrylic oligo/resin.
4. The composition of claim 1, wherein the adhesion promoting component comprises 2-(2-ethoxyethoxy)ethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, or combinations thereof.
5. The composition of claim 4, wherein the adhesion promoting component comprises 2-(2-ethoxyethoxy)ethyl (meth)acrylate.
6. The composition of claim 4, wherein the adhesion promoting component comprises tetrahydrofurfuryl (meth)acrylate.
7. The composition of claim 1, wherein the adhesion promoting component comprises N-vinylcaprolactam.
8. A radiation curable, ink jettable fluid composition, comprising:
(a) an oligo/resin component; and (b) a radiation curable reactive diluent, wherein the reactive diluent comprises a high Tg component, an adhesion promoting component, and at least one multifunctional monomer having a plurality of radiation curable moieties, wherein the adhesion promoting component comprises 0.1 to 50 weight percent of at least one of a heterocyclic radiation curable monomer, and/or a monomer comprising a pendant alkoxylated moiety.
9. The radiation curable, ink jettable composition of claim 8, wherein the adhesion promoting component comprises a heterocyclic radiation curable monomer.
10. The radiation curable, ink jettable composition of claim 8, wherein the adhesion promoting component comprises a radiation curable monomer comprising a pendant alkoxylated moiety.
11. The ink composition of claim 8, wherein the oligo/resin component is aliphatic.
12. The ink composition of claim 8, wherein the oligo/resin component comprises an oligo/resin selected from the group consisting of an aliphatic polyester oligo/resin, an aliphatic polyurethane oligo/resin, and an aliphatic acrylic oligo/resin.
13. The ink jettable fluid composition of claim 8, wherein the composition is substantially free of solvent.
14. The ink jettable fluid composition of claim 8, wherein the reactive diluent comprises 0.5 to 50 weight percent of the high Tg component, 0.5 to 70 weight percent of the adhesion promoting component, and 0.5 to 50 weight percent of the one multifunctional monomer having a plurality of radiation curable moieties.
15. The ink jettable fluid composition of claim 14, wherein the high Tg component comprises a monomer, said monomer comprising at least one radiation curable moiety and at least one nonaromatic, cyclic moiety.
16. The ink jettable composition of claim 14, wherein the high Tg component comprises isobornyl (meth)acrylate.
17. The ink jettable composition of claim 8, wherein the multifunctional monomer comprises hexanediol di(meth)acrylate.
18. The ink jettable composition of claim 14, wherein the adhesion promoting component comprises a monomer having an adhesion score after curing of at least 50 according to ASTM D 3359-95A, Method B on at least one substrate chosen from the group consisting of polymethyl methacrylate, polyvinyl chloride, and polyethylene terephthalate.
19. The ink jettable composition of claim 14, wherein the adhesion promoting component comprises a monomer, said monomer comprising at least one radiation curable moiety and pendant alkoxylated functionality.
20. The ink jettable composition of claim 14 wherein the adhesion promoting component comprises 2-(2-ethoxyethoxy)ethyl (meth)acrylate.
21. The ink jettable composition of claim 14, wherein the adhesion promoting component comprises a monomer, said monomer comprising at least one radiation curable moiety and at least one heterocyclic moiety.
22. The ink jettable composition of claim 21, wherein said monomer is tetrahydrofurfuryl (meth)acrylate.
23. The composition of claim 14, wherein the adhesion promoting component comprises N-vinylcaprolactam.
24. The composition of claim 14, wherein the adhesion promoting component comprises propoxyethyl (meth)acrylate.
25. The composition of claim 14, wherein the adhesion promoting component comprises propoxylated neopentyl glycol di(meth)acrylate.
26. The ink jettable composition of claim 26, wherein the adhesion promoting component comprises 1 to 10 parts by weight of a first monomer comprising at least one radiation curable moiety and pendant alkoxylated functionality per 5 to 15 parts by weight of a second monomer comprising at least one radiation curable moiety and at least one heterocyclic moiety.
27. The ink jettable composition of claim 19, wherein the first monomer is 2-(2-ethoxyethoxy)ethyl (meth)acrylate and the second monomer is tetrahydrofurfuryl (meth)acrylate.
28. A radiation curable, ink jettable fluid composition, comprising:
(a) an oligo/resin component; and (b) a radiation curable reactive diluent, wherein the reactive diluent comprises an adhesion promoting component, said adhesion promoting component comprising an alkoxylated, radiation curable monomer and a radiation curable monomer comprising a heterocyclic moiety.
29. The ink composition of claim 21, wherein the oligo/resin component is aliphatic.
30. The ink composition of claim 21, wherein the oligo/resin component comprises an oligo/resin selected from the group consisting of an aliphatic polyester oligo/resin, an aliphatic polyurethane oligo/resin, and an aliphatic acrylic oligo/resin.
31. The ink jettable fluid composition of claim 21, wherein the composition is substantially free of solvent.
32. The ink jettable composition of claim 21, wherein the adhesion promoting component comprises 1 to 10 parts by weight of a first monomer comprising at least one radiation curable moiety and at least one alkoxy or polyalkoxy moiety per 5 to 15 parts by weight of a second monomer comprising at least one radiation curable moiety and at least one heterocyclic moiety.
33. The ink jettable composition of claim 21, wherein the first monomer is 2-(2-ethoxyethoxy)ethyl (meth)acrylate and the second monomer is tetrahydrofurfuryl (meth)acrylate.
34. A radiation curable, ink jettable fluid composition, comprising:
(a) an oligo/resin component; and (b) a radiation curable reactive diluent, wherein the reactive diluent comprises an adhesion promoting component, a high Tg component, a low surface tension component comprising a radiation curable monomer having a hydrocarbyl moiety containing 2 to 20 carbon atoms, and a multifunctional monomer having a plurality of radiation curable moieties.
35. The radiation curable, ink jettable fluid composition of claim 34, wherein the oligo/resin component is aliphatic.
36. The radiation curable, ink jettable fluid composition of claim 34, wherein the oligo/resin component comprises an oligo/resin selected from the group consisting of an aliphatic polyester oligo/resin, an aliphatic polyurethane oligo/resin, and an aliphatic acrylic oligo/resin.
37. The ink jettable fluid composition of claim 34, wherein the composition is substantially free of solvent.
38. The ink jettable fluid composition of claim 34, wherein the reactive diluent comprises 0.5 to 50 weight percent of the high Tg component, 0.5 to 70 weight percent of the adhesion promoting component, and 0.5 to 50 weight percent of the one multifunctional monomer having a plurality of radiation curable moieties
39. The ink jettable fluid composition of claim 38, wherein the high Tg component comprises a monomer, said monomer comprising at least one radiation curable moiety and at least one nonaromatic, cyclic moiety.
40. The ink jettable composition of claim 38, wherein the high Tg component comprises isobornyl (meth)acrylate.
41. The ink jettable composition of claim 34, wherein the multifunctional monomer comprises 1,6-hexanediol di(meth)acrylate.
42. The ink jettable composition of claim 38, wherein the adhesion promoting component comprises a monomer having an adhesion score after curing of at least 50 according to ASTM D 3359-95A, Method B on at least one substrate chosen from the group consisting of polymethyl methacrylate, polyvinyl chloride, and polyethylene terephthalate.
43. The ink jettable composition of claim 38, wherein the adhesion promoting component comprises a monomer, said monomer comprising at least one radiation curable moiety and one or more alkoxy or polyalkoxy moieties.
44. The ink jettable composition of claim 38, wherein the adhesion promoting component comprises 2-(2-ethoxyethoxy)ethyl (meth)acrylate.
45. The ink jettable composition of claim 38, wherein the adhesion promoting component comprises a monomer, said monomer comprising at least one radiation curable moiety and at least one heterocyclic moiety.
46. The ink jettable composition of claim 45, wherein said monomer is tetrahydrofurfuryl (meth)acrylate.
47. The ink jettable composition of claim 38, wherein the adhesion promoting component comprises 1 to 10 parts by weight of a first monomer comprising at least one radiation curable moiety and at least one alkoxy or polyalkoxy moiety per 5 to 15 parts by weight of a second monomer comprising at least one radiation curable moiety and at least one heterocyclic moiety.
48. The ink jettable composition of claim 47, wherein the first monomer is 2-(2-ethoxyethoxy)ethyl (meth)acrylate and the second monomer is tetrahydrofurfuryl (meth)acrylate.
49. The composition of claim 38, wherein the adhesion promoting component comprises N-vinyl caprolactam.
50. The composition of claim 38, wherein the adhesion promoting component comprises propoxy ethyl (meth)acrylate.
51. The composition of claim 38, wherein the adhesion promoting component comprises propoxylated neopentyl glycol di(meth)acrylate.
52. The ink jettable composition of claim 34, wherein the low surface tension component comprises a monomer comprising at least one radiation curable moiety and a branched hydrocarbyl moiety containing 3 to 20 carbon atoms.
53. The ink jettable composition of claim 34, wherein the low surface tension component comprises a branched alkyl (meth)acrylate.
54. The ink jettable composition of claim 53, wherein said branched alkyl (meth)acrylate is isooctyl (meth)acrylate.
55. The radiation curable, ink jettable fluid composition of claim 34, further comprising a radiation curable gloss component.
56. The radiation curable, ink jettable fluid composition of claim 55, wherein the gloss component comprises a radiation curable monomer that is a solid at room temperature.
57. The radiation curable, ink jettable fluid composition of claim 55, wherein the gloss component comprises N-vinyl pyrrolidinone.
58. A radiation curable ink composition, comprising:
an oligo/resin component;
a radiation curable, reactive diluent; and wherein the ink composition is substantially free of solvent and has at least about 50 percent elongation in a cured state, an ink jettable viscosity in an uncured state, and wherein the ink composition is at least a substantially Newtonian fluid in the uncured state.
59. The ink composition of claim 58, further comprising a colorant.
60. The ink composition of claim 58, wherein the composition is substantially free of colorant.
61. A radiation curable ink composition that has an ink jettable viscosity in an uncured state and at bast about 50 percent elongation in a cured state, wherein the ink composition comprises an oligo/resin component selected from the group consisting of an aliphatic polyester oligo/resin, an aliphatic polyurethane oligo/resin, and an aliphatic acrylic oligo/resin.
62. The composition of claim 61, wherein the composition is substantially free of solvent.
63. A radiation curable ink jettable composition comprising tetrahydroturturyl (meth)acrylate.
CA2425945A 2000-11-09 2001-11-07 Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications Expired - Fee Related CA2425945C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US71133600A 2000-11-09 2000-11-09
US09/711,336 2000-11-09
PCT/US2001/046508 WO2002038688A2 (en) 2000-11-09 2001-11-07 Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications

Publications (2)

Publication Number Publication Date
CA2425945A1 true CA2425945A1 (en) 2002-05-16
CA2425945C CA2425945C (en) 2010-01-26

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CA2425945A Expired - Fee Related CA2425945C (en) 2000-11-09 2001-11-07 Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications

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US (2) US7423072B2 (en)
EP (1) EP1355999B1 (en)
JP (3) JP2004514014A (en)
KR (1) KR100856444B1 (en)
CN (1) CN1484680B (en)
AU (2) AU2002230607B2 (en)
CA (1) CA2425945C (en)
MX (1) MXPA03003997A (en)
WO (1) WO2002038688A2 (en)

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