Ink coating formulations and polymerizable systems for producing the same

• US 9,234,107 B2
• Filed: 03/29/2013
• Issued: 01/12/2016
• Est. Priority Date: 03/30/2012
• Status: Active Grant

• Current Assignee: Nippon Shokubai Company Limited
• Original Assignee: Sirrus, Inc (Nippon Shokubai Company Limited)
• Inventors: Malofsky, Bernard M., Malofsky, Adam G., Ellison, Matthew M.
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): WHITELEY, JESSICA
• Application Number:
  US14/388,582
• Publication Number:
  US 20150104660A1
• Time in Patent Office: 1,019 Days
• Field of Search: 522/1, 520/1
• US Class Current: 1/1
• CPC Class Codes: C08F 222/10 Esters
• CPC Class Codes: C08F 222/14 Esters having no free carboxylic acid groups , e.g. dialkyl maleates or fumarates
• CPC Class Codes: C08K 2003/2241 Titanium dioxide
• CPC Class Codes: C08K 3/22 of metals
• CPC Class Codes: C08K 5/23 Azo-compounds
• CPC Class Codes: C08K 5/3437 condensed with carbocyclic rings
• CPC Class Codes: C08K 5/3467 having more than two nitrogen atoms in the ring
• 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
• CPC Class Codes: C09D 11/106 containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 11/107 from unsaturated acids or derivatives thereof
• CPC Class Codes: C09D 11/322 Pigment inks
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09D 5/002 Priming paints C09D5/08 takes precedence
• CPC Class Codes: C09D 5/20 for coatings strippable as coherent films, e.g. temporary coatings strippable as coherent films
• CPC Class Codes: C09D 7/40 Additives
• CPC Class Codes: Y10T 428/31935 Ester, halide or nitrile of addition polymer

Abstract

Ink and coating compositions, printing and coating processes, and printed and coated substrates utilizing a polymerizable composition comprising one or more di-activated vinyl compounds, with the proviso that said a di-activated vinyl compound is not a cyanoacrylate. Exemplary compositions include methylene malonates, methylene β-ketoesters, methylene β-diketones, dialkyl disubstituted vinyls, and dihaloalkyl disubstituted vinyls. Exemplary compositions are polymerizable at ambient temperatures.

Claims

1. A composition comprising a polymerizable composition, the polymerizable composition comprising:

a multifunctional di-activated vinyl compound, the multifunctional di-activated vinyl compound being selected from the group consisting of methylene malonate, methylene β

-ketoester, methylene β

-diketone, dialkyl disubstitued vinyl, dihaloalkyl disubstituted vinyl, and combinations thereof; and

a coloring agent; and

wherein the polymerizable composition is curable at ambient temperature.

2. The composition according to claim 1, wherein the coloring agent comprises one or more members of the group consisting of:

organic pigment, organometallic pigment, mineral-based pigment, carbon pigments, titanium pigment, azo compound, quinacridone compound, phthalocyanine compound, cadmium pigment, chromium pigment, cobalt pigment, copper pigment, iron pigment, clay earth pigment, lead pigment, mercury, titanium pigment, aluminum pigment, manganese pigment, ultramarine pigment, zinc pigment, arsenic pigment, tin pigment, iron oxide pigment, antimony pigment, barium pigment, a biological pigment, dye, photochromic, conductive and liquid crystal polymer pigment, piezochromic pigment, goniochromatic pigment, silver pigment, diketopyrrolo-pyrrole, benzimidazolone, isoindoline, isoindolinone, and radio-opacifier.

3. The composition according to claim 1, wherein the polymerizable composition exhibits a shelf-life of 6 months or greater at ambient temperature.

4. The composition according to claim 1, further comprising a polymerization activator, wherein the polymerization activator is in the form of a base, a base precursor, a base converter, or base enhancer.

5. The composition according to claim 1, further comprising a formulation additive.

6. The composition according to claim 5, wherein the formulation additive comprises one or more of plasticizers, thixotropic agents, adhesion promoters, antioxidants, light stabilizers, UV stabilizers, fillers, surfactants, wetting agents, viscosity modifiers, extenders, dispersants, anti-blocking agents, defoamers, air release agents, anti-sagging agents, anti-setting agents, matting agents, flattening agents, waxes, anti-mar additives, anti-scratch additives, and inert resins.

7. The composition according to claim 4, wherein the polymerization activator comprises one or more of an organic material, an inorganic material, and an organometallic material.

8. The composition according to claim 7, wherein the polymerization activator comprises one or more of:

sodium acetate;

potassium acetate;

acid salts of sodium, potassium, lithium, copper, and cobalt;

tetrabutyl ammonium fluoride, chloride, and hydroxide;

an amine whether primary, secondary or tertiary;

an amide;

salts of polymer bound acids;

benzoate salts;

2,4-pentanedionate salts;

sorbate salts;

propionate salts;

secondary aliphatic amines;

piperidene, piperazine, N-methylpiperazine, dibutylamine, morpholine, diethylamine, pyridine, triethylamine, tripropylamine, triethylenediamine, N,N-dimethylpiperazine, butylamine, pentylamine, hexylamine, heptylamine, nonylamine, decylamine;

salts of amines with organic monocarboxylic acids;

piperidine acetate;

metal salt of a lower monocarboxylic acid;

copper(II) acetate, cupric acetate monohydrate, potassium acetate, zinc acetate, zinc chloracetate, magnesium chloracetate, magnesium acetate; and

salts of polyacrylic acid copolymers.

9. The composition according to claim 1, wherein the multifunctional di-activated vinyl compound comprises one or more of methylene malonate, methylene β

-ketoester, and methylene β

-diketone.

10. The composition according to claim 1, wherein the methylene malonate is a diethyl methylene malonate, dimethyl methylene malonate, di-n-propyl methylene malonate, di-isopropyl methylene malonate, or dibenzyl methylene malonate.

12. The composition according to claim 10, wherein the multifunctional di-activated vinyl compound is diethyl methylene malonate and the polymerizable composition further comprises the transesterification product of diethyl methylene malonate and hexane diol.

13. The composition according to claim 10, wherein the methylene malonate is a diethyl methylene malonate.

15. The composition according to claim 1, wherein the multifunctional di-activated vinyl compound comprises two or more units represented by the structure:

—

W—

C(O)—

C(═

CH₂)—

C(O)—

W—

, where W represents —

O—

or a direct bond.

11. A composition comprising a polymerizable composition, the polymerizable composition comprising:

a di-activated vinyl compound, the di-activated vinyl compound being selected from the group consisting of methylene malonate; and

a coloring agent; and

wherein the methylene malonate is a mixture of difunctional and multifunctional monomers and one or more monofunctional monomers; and

wherein the polymerizable composition is curable at ambient temperature.

14. A composition comprising a polymerizable composition, the polymerizable composition comprising:

a di-activated vinyl compound, the di-activated vinyl compound selected from the group consisting of a multifunctional diethyl methylene malonate; and

a coloring agent; and

wherein the polymerizable composition is curable at ambient temperature.