Ink coating formulations and polymerizable systems for producing the same

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.

What is claimed is: 
     
         1 . A coated article comprising:
 a substrate;   a cured coating on at least a portion of the substrate, the cured coating formed from a polymerizable composition; and   wherein the polymerizable composition comprises:
 a di-activated vinyl compound selected from the group consisting of methylene malonate, methylene β-ketoester, methylene β-diketone, dialkyl disubstituted vinyl, dihaloalkyl disubstituted vinyl, and combinations thereof; and 
 a coloring agent; and 
 wherein the polymerizable composition is solvent free. 
   
     
     
         2 . The coated article of  claim 1 , wherein the substrate comprises one or more of a plant-based material, a plastic-based material, a carbon-based material, a metal-based material, and a glass-based material. 
     
     
         3 . The coated article of  claim 1 , wherein the substrate comprises one or more of paper, oak, Douglass fir, balsa, polyphenylene ether (“PPE”), polycarbonate (“PC”), silicon, glass, fiberglass, silver coated copper, copper, steel, and aluminum. 
     
     
         4 . The coated article of  claim 1  comprises an automobile component, an electronics component, a metal can, a plastic container, or a construction material. 
     
     
         5 . The coated article of  claim 1 , wherein the coating exhibits a 5B or stronger result on the ASTM D3359 standard. 
     
     
         6 . The coated article of  claim 1 , wherein the coating exhibits a 6H or stronger result on the ASTM D3363 standard. 
     
     
         7 . The coated article of  claim 1  comprises a thermally sensitive material. 
     
     
         8 . The coated article of  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. 
     
     
         9 . The coated article of  claim 1 , wherein the at least a portion of the substrate comprises a surface coupling agent, the surface coupling agent comprising one or more of a silane coupling agent and a titanate coupling agent. 
     
     
         10 . The coated article of  claim 1 , wherein the polymerizable composition further comprises a polymerization activator, the polymerization activator comprising one or more of a base, a base precursor, a base converter, and a base enhancer. 
     
     
         11 . The coated article of  claim 10 , wherein the polymerization activator comprises one or more of an organic material, an inorganic material, and an organometallic material. 
     
     
         12 . The coated article of  claim 10 , wherein the polymerization activator comprises one or more of: phenolformaldehyde; 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, tri ethylenediamine, 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. 
     
     
         13 . The coated article of  claim 10 , wherein the polymerization activator comprises about 2% or less of the polymerizable composition by weight. 
     
     
         14 . The coated article of  claim 1 , wherein the polymerizable composition further comprises a formulation additive. 
     
     
         15 . The coated article of  claim 14 , wherein the formulation additive comprises one or more 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. 
     
     
         16 . The coated article of  claim 14 , wherein the formulation additive comprises one or more of hydroquinone monomethyl ether and methane sulfonic acid. 
     
     
         17 . The coated article of  claim 1 , wherein the di-activated vinyl compound comprises diethyl methylene malonate. 
     
     
         18 . The coated article of  claim 1 , wherein the di-activated vinyl compound comprises a difunctional or multifunctional di-activated vinyl compound. 
     
     
         19 . The coated article of  claim 1 , wherein the cured coating is crosslinked. 
     
     
         20 . The coated article of  claim 1 , further comprising one or more additional coatings, each of the one or more additional coatings formed from one or more additional polymerizable compositions; and
 wherein each of the one or more additional polymerizable compositions comprises a di-activated vinyl compound selected from the group consisting of methylene malonate, methylene β-ketoester, methylene β-diketone, dialkyl disubstituted vinyl, dihaloalkyl disubstituted vinyl, and combinations thereof.