CN113201245B - Active energy ray-curable ink for offset lithography and printed matter - Google Patents
Active energy ray-curable ink for offset lithography and printed matter Download PDFInfo
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- CN113201245B CN113201245B CN202110078508.3A CN202110078508A CN113201245B CN 113201245 B CN113201245 B CN 113201245B CN 202110078508 A CN202110078508 A CN 202110078508A CN 113201245 B CN113201245 B CN 113201245B
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- meth
- acrylate
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- active energy
- energy ray
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- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 9
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 235000020679 tap water Nutrition 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- XTXFUQOLBKQKJU-UHFFFAOYSA-N tert-butylperoxy(trimethyl)silane Chemical compound CC(C)(C)OO[Si](C)(C)C XTXFUQOLBKQKJU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
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
- C09D11/02—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
Abstract
The present invention provides an active energy ray-curable offset printing ink which, even without using diallyl phthalate resin, exhibits the same or better printing ink characteristics as when using the resin. An active energy ray-curable ink for offset lithography, characterized by comprising a copolymer A and a methacrylate compound B, wherein the copolymer A comprises a polymer containing, as essential polymerization components, a specific amount of the following components, wherein the total amount of a to f is 100% by mass, and the components are: a polyfunctional (meth) acrylate compound having 2 to 6 functional groups; b (meth) acrylic acid aryl ester compound; c a styrene compound; d a compound having a hydrophilic group and having a polymerizable unsaturated bond; e a (meth) acrylate compound having a nitrogen-containing heterocyclic group; and f a (meth) acrylate compound having an alkylamino group.
Description
Technical Field
The present invention relates to an active energy ray-curable ink for offset lithography, which uses a film substrate and a paper as a substrate. Further, the present invention relates to a printed matter using the ink.
Background
Since the active energy ray-curable ink is solvent-free and is instantly cured and dried by active energy rays, it is considered that the ink is environmentally friendly, excellent in printing workability, and capable of producing high-quality printed matter, and is used as an ink in various printing methods in combination with: lithographic printing (lithographic printing using a fountain solution, waterless lithographic printing without a fountain solution), letterpress printing, intaglio printing, stencil printing, and transfer (offset) printing in which an ink adhering to these plates is transferred to an intermediate transfer member such as a blanket and then printed on a printing object, and is suitable for various printed matter such as foam printed matter, various book printed matter, various packaging printed matter such as cardboard, various plastic printed matter, decal paper, label printed matter, art printed matter, metal printed matter (art printed matter, beverage can printed matter, food printed matter such as cans, etc.), and the like. Among them, offset active energy ray-curable inks for printing on a printing object by transferring an ink attached to a plate for offset printing to an intermediate transfer body such as a blanket (blanket) and then printing the ink on paper, plastic substrates, flexible packaging substrates used in the field of food packaging, and the like are widely used as high-speed printing systems.
Conventionally, diallyl phthalate resins, urethane resins, polyester resins, and the like have been generally used as binder resins for active energy ray-curable inks for offset lithography (for example, patent document 1). Among them, diallyl phthalate resins are characterized by high elasticity and flowability, and it has been difficult to find other binder resins having high elasticity and flowability equivalent to that of diallyl phthalate resins. On the other hand, in the case of diallyl phthalate resins, unreacted diallyl phthalate monomers (diallyl phthalate, CAS No. 131 to 17 to 9) remaining in the resins are the primary second type of monitoring chemicals and are high risk substances for mutagenicity (GHS classification 1B (germ cell mutagenicity)), so that the demand for diallyl phthalate resins is increasing in active energy ray curable ink applications for offset lithography. (see, for example, paragraph 0009 of patent document 3)
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2015-193677
Patent document 2: japanese patent application laid-open No. 2015-174994
Patent document 3: WO14/129461
Disclosure of Invention
Problems to be solved by the invention
The present invention addresses the problem of providing an active energy ray-curable ink for offset lithography, which exhibits ink characteristics similar to or better than those exhibited when using a diallyl phthalate resin, even if the diallyl phthalate resin is not used.
Means for solving the problems
The present inventors have made intensive studies to solve the above problems, and as a result, have found that the above problems are solved by containing a specific acrylic copolymer (a) and a (meth) acrylate compound (B).
Specifically, the present invention provides an active energy ray-curable ink for offset lithography, which contains a copolymer (a) containing a polymer containing, as essential polymerization components, (wherein the total amount of (a) to (f) is 100 mass%), and a (meth) acrylate compound (B), the components being:
5 to 70 mass% of (a) a multifunctional (meth) acrylate compound having 2 to 6 functional groups;
0.1 to 50 mass% of (b) an aryl (meth) acrylate compound;
5 to 40 mass% of (c) a styrene compound;
0.1 to 10% by mass of (d) a compound having a hydrophilic group and containing a polymerizable unsaturated bond;
0.1 to 10 mass% of (e) a (meth) acrylate compound having a nitrogen-containing heterocyclic group; and
0.1 to 10% by mass of (f) a (meth) acrylate compound having an alkylamino group.
The present invention also provides a printed matter comprising the above-described cured product of the active energy ray-curable ink for offset lithography on a substrate.
Effects of the invention
According to the present invention, it is possible to provide an active energy ray-curable ink for offset lithography which exhibits the same ink characteristics as those when using a diallyl phthalate resin, even if a diallyl phthalate resin is not used.
The active energy ray-curable ink for offset lithography of the present invention can be suitably used as an ink for offset lithography using a fountain solution.
Detailed Description
(definition of terms)
In the present invention, "(meth) acrylate" means one or both of acrylate and methacrylate, and "(meth) acryl" means one or both of acryl and methacryl.
(copolymer (A))
The copolymer (a) used in the present invention contains a polymer containing, as an essential polymerization component, (wherein the total amount of (a) to (f) is 100 mass%), the components being:
5 to 70 mass% of (a) a multifunctional (meth) acrylate compound having 2 to 6 functional groups;
0.1 to 40 mass% of (b) an aryl (meth) acrylate compound;
5 to 40 mass% of (c) a styrene compound;
0.1 to 10% by mass of (d) a compound having a hydrophilic group and containing a polymerizable unsaturated bond;
0.1 to 10 mass% of (e) a (meth) acrylate compound having a nitrogen-containing heterocyclic group; and
0.1 to 10% by mass of (f) a (meth) acrylate compound having an alkylamino group.
Examples of the (a) polyfunctional (meth) acrylate compound having 2 to 6 functional groups which is the essential component of the copolymer (A) include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, (meth) allyl acrylate, trimethylolpropane tri (meth) acrylate, tetramethylolmethane tri (meth) acrylate, tetramethylolethane tri (meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate pentaerythritol tetra (meth) acrylate, sorbitol tetra (meth) acrylate, trimethylolpropane tetra (meth) acrylate, dimethylolethane tetra (meth) acrylate, dimethylolbutane tetra (meth) acrylate, dimethylolhexane tetra (meth) acrylate, dimethylolpropane tetra (meth) acrylate, trimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, and pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate propionate, pentaerythritol tetra (meth) acrylate ethoxylate, sorbitol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol hexa (meth) acrylate, sorbitol hexa (meth) acrylate, and the like. Only 1 of them may be used alone, or 2 or more may be used in combination.
Examples of the (b) aryl (meth) acrylate compound which is an essential polymerization component of the copolymer (a) include benzyl (meth) acrylate, phenoxy ethylene glycol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, phenyl (meth) acrylate, ethoxylated ortho-phenylphenol (meth) acrylate, and the like. Only 1 of them may be used alone, or 2 or more may be used in combination.
Examples of the styrene compound (c) which is an essential polymerization component of the copolymer (A) include alkylstyrenes such as styrene, α -methylstyrene, β -methylstyrene, 2, 4-dimethylstyrene, α -ethylstyrene, α -butylstyrene, α -hexylstyrene, halogenated styrenes such as 4-chlorostyrene, 3-chlorostyrene and 3-bromostyrene, 3-nitrostyrene and 4-methoxystyrene. Only 1 of them may be used alone, or 2 or more may be used in combination.
Examples of the compound having a polymerizable unsaturated bond, which is an essential polymerization component of the copolymer (a), that is, (d) a compound having a hydrophilic group include acrylic acid, methacrylic acid, maleic anhydride, maleic acid, fumaric acid, itaconic acid, 2- (meth) acryloyloxyethyl succinate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate (n representing the degree of polymerization of polyethylene glycol is 3 to 23), and the like. Only 1 of them may be used alone, or 2 or more may be used in combination.
The (e) acrylic acid ester having a nitrogen-containing heterocyclic group, which is an essential polymerization component of the copolymer (a), includes, for example, acryloylmorpholine, 3-acryl-2-oxazolidone, and the like. Only 1 of them may be used alone, or 2 or more may be used in combination.
Examples of the (meth) acrylic acid ester having an alkylamino group as the essential polymerization component of the copolymer (A) include dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate. Only 1 of them may be used alone, or 2 or more may be used in combination.
The weight average molecular weight of the copolymer (A) used in the present invention is 5000 to 100000. Among them, the range of 10000 to 80000 is preferable, and the range of 20000 to 70000 is more preferable. The weight average molecular weight is a value measured by GPC (gel permeation chromatography), and is a value converted to a molecular weight of polystyrene used as a standard substance.
The copolymer (A) used in the present invention has a PDI of 3 to 35 in molecular weight. Among them, the range of 5 to 30 is preferable, and the range of 8 to 25 is more preferable. The molecular weight PDI is abbreviated as molecular weight dispersity (Poly Dispersity Index, PDI) and is a value obtained by dividing the weight average molecular weight measured by GPC method by the number average molecular weight measured by GPC method.
The acid value of the copolymer (A) used in the present invention is 1 to 40mg/KOH/g. The acid value was obtained by using japanese industrial standard "K0070:1992, acid value, saponification value, ester value, iodine value, hydroxyl value and unsaponifiable matter test method "of chemical products.
In the copolymer (a), the compounds (a) to (f) are blended in a range satisfying the following conditions, and polymerized by a known method, to obtain a polymer, wherein the conditions are:
5 to 70 mass% of (a) a multifunctional (meth) acrylate compound having 2 to 6 functional groups;
0.1 to 40 mass% of (b) an aryl (meth) acrylate compound;
5 to 50 mass% of (c) a styrene compound;
0.1 to 10% by mass of (d) a compound having a hydrophilic group and containing a polymerizable unsaturated bond;
0.1 to 10 mass% of (e) a (meth) acrylate compound having a nitrogen-containing heterocyclic group; and
0.1 to 10% by mass of (f) a (meth) acrylate compound having an alkylamino group. Wherein the blending is performed such that the total amount of (a) to (f) is 100 mass%.
Among the above ratios, more preferable are:
10 to 70 mass% of (a) a multifunctional (meth) acrylate compound having 2 to 6 functional groups;
5 to 35 mass% of (b) an aryl (meth) acrylate compound;
10 to 45 mass% of (c) a styrene compound;
0.5 to 8 mass% of (d) a compound having a hydrophilic group and containing a polymerizable unsaturated bond;
1 to 8 mass% of (e) a (meth) acrylate compound having a nitrogen-containing heterocyclic group; and
0.5 to 8 mass% of (f) a (meth) acrylate compound having an alkylamino group, (wherein the blending is performed such that the total amount of (a) to (f) is 100 mass%), and more preferably:
20 to 70 mass% of (a) a polyfunctional (meth) acrylate compound having 2 to 6 functional groups;
10 to 30 mass% of (b) an aryl (meth) acrylate compound;
15 to 40 mass% of (c) a styrene compound;
1 to 7 mass% of (d) a compound having a hydrophilic group and containing a polymerizable unsaturated bond;
2 to 6 mass% of (e) a (meth) acrylate compound having a nitrogen-containing heterocyclic group; and
0.5 to 6% by mass of (f) a (meth) acrylic acid ester compound having an alkylamino group, (wherein the blending is performed such that the total amount of (a) to (f) is 100% by mass).
The copolymer (a) can be obtained by a known method such as a solution polymerization method.
Examples of the solvent include aromatic hydrocarbon solvents, ketone solvents, ether solvents, and ester solvents. Only 1 of them may be used alone, or 2 or more may be used in combination. For example, 50 to 500 parts by mass of a solvent is preferably used per 100 parts by mass of the total amount of the polymerization components of the copolymer (A).
In polymerizing the above-mentioned polymerization component, for example, a radical polymerization initiator may be used. The radical polymerization initiator is not particularly limited, and for example, inorganic peroxides, organic peroxides, azo compounds, and the like can be used.
Specific examples of the radical polymerization initiator include inorganic peroxides such as ammonium persulfate and potassium persulfate, organic peroxides such as benzoyl peroxide, t-butyl peroxyacetate, 2-bis (t-butylperoxybutane), t-butyl peroxybenzoate, n-butyl 4, 4-bis (t-butylperoxyisopropyl) benzene, dicumyl peroxide, di-t-hexyl peroxide, 2, 5-dimethyl-2, 5, -di (t-butylperoxy) hexane, t-butylcumyl peroxide, di-t-butyl peroxide, dicumyl hydroperoxide, p-menthane hydroperoxide, 1, 3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-butyltrimethylsilyl peroxide, and azo compounds such as 4,4 '-azobis (4-cyanovaleric acid), 2' -azobis (2-methylpropanenitrile), 2 '-azobis (2-methylbutanenitrile), and 2,2' -azobis (2, 4-dimethylpentanenitrile). Only 1 of them may be used alone, or 2 or more may be used in combination. The radical polymerization initiator is preferably used in an amount of 0.1 to 20 parts by mass based on 100 parts by mass of the total amount of the polymerization components.
In polymerizing the above-mentioned polymerization components, for example, a chain transfer agent may be used. The chain transfer agent is not particularly limited, and examples thereof include lauryl mercaptan, dodecyl mercaptan, 2-mercaptobenzothiazole, bromotrichloromethane, and the like. Only 1 of them may be used alone, or 2 or more may be used in combination. These chain transfer agents are preferably used in an amount of 0.01 to 5 parts by mass based on 100 parts by mass of the total amount of the above-mentioned polymeric components.
The copolymer (a) used in the present invention is preferably used in a range of 5 to 30 mass%, more preferably in a range of 15 to 25 mass%, relative to the total amount of the active energy ray-curable ink.
((meth) acrylate Compound (B))
The (meth) acrylate compound (B) used in the present invention may be any of (meth) acrylates commonly used in active energy ray-curable ink technology. Specifically, monofunctional (meth) acrylates and polyfunctional (meth) acrylates are exemplified.
Examples of the monofunctional (meth) acrylate include ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isopentyl (meth) acrylate, isodecyl (meth) acrylate, isostearyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, nonylphenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, glycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, nonylphenoxyethyl tetrahydrochysene (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and the like.
Examples of the (meth) acrylate having a function of 2 or more include 2-membered alcohol (e.g., 1, 4-butanediol di (meth) acrylate, 3-methyl-1, 5-pentanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2-methyl-1, 8-octanediol di (meth) acrylate, 2-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, tri (2-hydroxyethyl) isocyanurate di (meth) acrylate, ethylene oxide or propylene oxide di (meth) acrylate obtained by adding 4 moles of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol, ethylene oxide di (meth) acrylate obtained by adding 2 moles of bisphenol a to 1 mole of ethylene oxide or propylene oxide, and pentaerythritol tri (meth) acrylate And poly (meth) acrylates of 3-or more-membered polyols such as pentaerythritol tetra (meth) acrylate, trimethylolpropane tetra (meth) acrylate, and dipentaerythritol poly (meth) acrylate, tri (meth) acrylates of triols obtained by adding 3 or more moles of ethylene oxide or propylene oxide to 1 mole of glycerin, di (meth) acrylates or tri (meth) acrylates of triols obtained by adding 3 or more moles of ethylene oxide or propylene oxide to 1 mole of trimethylolpropane (trimethylolpropane ethylene oxide modified tri (meth) acrylates), and poly (meth) acrylates of polyoxyalkylene polyols such as di (meth) acrylates of diols obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of bisphenol a. These may be used alone or in combination of 2 or more.
Among them, the (meth) acrylate compound (B) is preferably at least one selected from dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, trimethylolpropane tetra (meth) acrylate, and trimethylolpropane ethylene oxide-modified tri (meth) acrylate.
The (meth) acrylate compound (B) is preferably used in a range of 20 to 70 mass%, more preferably in a range of 30 to 60 mass%, based on the total amount of the active energy ray-curable ink.
The copolymer (A) and the (meth) acrylate compound (B) are preferably blended in such a manner that the ratio thereof is in the range of 5:65 to 30:40, more preferably in the range of 15:55 to 25:45.
(extender pigment)
In the active energy ray-curable ink for offset lithography of the present invention, extender pigments are preferably used. As extender pigments, inorganic fine particles can be used. Examples of the inorganic fine particles include inorganic coloring pigments such as titanium oxide, graphite, and zinc white, inorganic pigments such as lime carbonate powder, precipitated calcium carbonate, precipitated barium sulfate, gypsum, clay (China Clay), silica, diatomaceous earth, talc, kaolin, alumina white, barium sulfate, aluminum stearate, calcium stearate, magnesium carbonate, barite powder, and rubstone powder (japanese text: ruber powder), inorganic extender pigments such as silicone, and glass beads. These inorganic fine particles have effects of adjusting the fluidity of the ink, preventing the ink from flying (bleeding), preventing the penetration into a printing substrate such as paper, and the like, and also have effects of suppressing paper peeling failure occurring during printing under low temperature conditions such as winter or during high-speed printing.
Among them, talc, magnesium carbonate and calcium carbonate are preferable from the viewpoint of suppressing paper peeling, and talc and magnesium carbonate are particularly preferable from the viewpoint of maintaining fluidity of the ink.
The talc, magnesium carbonate and calcium carbonate may be used alone or in combination of 2 or more. In the case of using the above talc, the content thereof is preferably in the range of 1 to 6 mass% of the total amount of the ink composition, and in the case of using magnesium carbonate or calcium carbonate, the content thereof is preferably in the range of 1 to 10 mass% of the total amount of the ink composition.
(other binder resin)
In the present invention, the copolymer (A) must be used, but various binder resins which are publicly known and commonly used may be used in combination. The binder resin mentioned here means all resins having suitable pigment affinity and dispersibility and having rheological properties required for printing ink, and examples of the non-reactive resin include diallyl phthalate resin, epoxy ester resin, urethane resin, polyester resin, petroleum resin, rosin ester resin, poly (meth) acrylate (excluding the above-mentioned acrylic copolymer (a) containing a styrene monomer and benzyl (meth) acrylate as essential polymerization components), cellulose derivatives, vinyl chloride-vinyl acetate copolymer, polyamide resin, polyvinyl acetal resin, butadiene-acrylonitrile copolymer, and the like, and epoxy acrylate compound, urethane acrylate compound, polyester acrylate compound, and the like having at least 1 or more polymerizable groups in the molecule may also be used.
The diallyl phthalate resin includes the 3 o-, m-, and p-isomers, but as the binder resin used in the active energy ray-curable ink for offset lithography of the present invention, diallyl phthalate resins (sometimes simply referred to as diallyl phthalate resins) and diallyl isophthalate resins may be used.
Examples of the diallyl isophthalate resin include a composition containing a polybasic acid such as phthalic acid as a main agent, allyl alcohol as a curing agent, and a crosslinking agent. Examples of the crosslinking agent include styrene and vinyl acetate.
Diallyl phthalate resins and diallyl isophthalate resins are particularly useful for imparting excellent paper release properties, emulsion resistance and long-term printing suitability.
Specifically, the diallyl phthalate resin may be Daiso dap A (manufactured by Osaka Soda Co., ltd.), and the diallyl isophthalate resin may be Daiso iso odap (manufactured by Osaka Soda Co., ltd.).
(photopolymerization initiator)
Next, if the curability of the ink is taken into consideration, the active energy ray curable ink for offset lithography of the present invention more preferably further contains a photopolymerization initiator.
When a photopolymerization initiator is used, examples thereof include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- [ 4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2' -dimethoxy-1, 2-diphenylethane-1-one, diphenyl (2, 4, 6-trimethoxybenzoyl) phosphine oxide, 2,4, 6-trimethylbenzoyl diphenylphosphine oxide, bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, and the like. These photopolymerization initiators may be used alone or in combination of 2 or more.
As the above-mentioned photopolymerization initiator, for example, "Omnirad-1173", "Omnirad-184", "Omnirad-127", "Omnirad-2959", "Omnirad-369", "Omnirad-379", "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", "Omnirad-754", "Omnirad-784", "Omnirad-500", "Omnirad-81" (manufactured by IGM corporation), "Kayacure-EPA", "Kayacure-MBP", "Kayacure-DMBI", "Kayacure-OA" (manufactured by Japanese chemical Co., ltd.), "VICURE-10", "VICURE-55" (manufactured by Stauffer Chemical), "Trigonal P1", "manufactured by Santa-Kayare-1000", "manufactured by means of Izoco.," UK..
The amount of the photopolymerization initiator added in the active energy ray-curable ink for offset lithography of the present invention is preferably in the range of 1 to 20 mass%, more preferably in the range of 5 to 15 mass% in terms of solid content. That is, when the total amount of the photopolymerization initiators is 1% by mass or more, good curability can be obtained, and when it is 20% by mass or less, unreacted polymerization initiators do not remain in the cured product, and curing failure can be suppressed. However, in the case of using an electron beam as an active energy ray, the use of these photopolymerization initiators is not essential in principle.
In addition, the active energy ray-curable ink for offset lithography can improve the curability of the cured coating film of the active energy ray-curable resin composition, and therefore, a photosensitizer may be further added as needed to improve curability.
Examples of the photosensitizer include amine compounds such as aliphatic amine and aromatic amine, urea compounds such as o-tolylthiourea, sulfur compounds such as sodium diethyldithiophosphate and p-toluenesulfonate of sec-benzylisothiouronium. The amount of the above-mentioned photosensitive agent used is preferably in the range of 1 to 20 mass% as the total amount of the above-mentioned alkylaminobenzophenone compound used, based on 100 mass% of the nonvolatile components in the active energy ray-curable ink of the present invention, from the viewpoint that the effect of improving curability is satisfactory.
(pigment)
The active energy ray-curable ink for offset lithography of the present invention contains a pigment as a colorant, and thereby functions as a printing ink imparting identification properties. In addition, when pigment is not contained, the varnish may be used as an overprint varnish (OP varnish) for the purpose of overcoating a printed layer. Examples of the pigment used as the coloring material include known and customary inorganic pigments and organic pigments.
Examples of the inorganic pigment include iron oxide, carbon black produced by a known method such as a contact method, a furnace method, or a thermal method.
Examples thereof include RAVEN 14, RAVEN 450, RAVEN 860Ultra, RAVEN1035, RAVEN 1040, RAVEN 1060Ultra, RAVEN 1080Ultra, RAVEN1180, RAVEN 1255 (above, manufactured by BIRLA), regal 250R, regal 400R, regal 330R, regal 660R, mogul L (above, manufactured by Cabot), MA7, MA8, MA11 (above, manufactured by Mitsubishi chemical Co.), and the like, and these may be used singly or in combination of 2 or more kinds as appropriate.
Examples of the organic pigment include quinacridone pigments, quinacridone quinone pigments, dioxazine pigments, phthalocyanine pigments, anthrapyrimidine (anthrarimidine) pigments, anthraanthone (anthantone) pigments, indanthrone (indanthrone) pigments, flavanthrone (flavanthrone) pigments, perylene pigments, diketopyrrolopyrrole pigments, viol pigments, quinophthalone pigments, anthraquinone pigments, thioindigo pigments, benzimidazolone pigments, and azo pigments. These pigments may be used alone or in combination of 2 or more.
Specific examples of the pigment used in the yellow ink include c.i. pigment yellow 1, 2, 12, 13, 14, 16, 17, 73, 74, 75, 83, 93, 95, 97, 98, 109, 110, 114, 120, 128, 129, 138, 150, 151, 154, 155, 174, 180, 185, and the like.
Specific examples of pigments used in the magenta ink include c.i. pigment red 5, 7, 12, 48 (Ca), 48 (Mn), 57 (Ca), and 57: 1. 112, 122, 123, 146, 168, 176, 184, 185, 202, 209, 269, etc., c.i. pigment violet 19, etc.
Specific examples of pigments used in the cyan ink include c.i. pigment blue 1, 2, 3, 15, and 15: 3. 15: 4. 16, 22, 60, 63, 66, etc.
(other additives)
The active energy ray-curable ink for offset lithography of the present invention may further contain other additives such as antioxidants, polymerization inhibitors, silicon-based additives, waxes, dyes, and the like, as necessary.
Examples of the antioxidant include hindered phenol antioxidants, hindered amine antioxidants, organic sulfur antioxidants, and phosphate antioxidants. These antioxidants may be used alone or in combination of 2 or more.
Examples of the silicon-based additive include a polyorganosiloxane having an alkyl group or a phenyl group, a polydimethylsiloxane having a polyether-modified acryl group, and a polydimethylsiloxane having a polyester-modified acryl group, such as a dimethylpolysiloxane, a methylphenyl polysiloxane, a cyclic dimethylpolysiloxane, a methyl hydrogen polysiloxane, a polyether-modified dimethylpolysiloxane copolymer, a polyester-modified dimethylpolysiloxane copolymer, a fluorine-modified dimethylpolysiloxane copolymer, and an amino-modified dimethylpolysiloxane copolymer. These silicon-based additives may be used alone or in combination of 2 or more.
To the active energy ray-curable ink for offset lithography of the present invention, wax may be added for the purpose of improving curability. Examples of the waxes include waxes such as paraffin wax, carnauba wax, beeswax, microcrystalline wax, polyethylene wax, oxidized polyethylene wax, polytetrafluoroethylene wax, and amide wax, and fatty acids having a carbon number in the range of about 8 to 18 such as coconut fatty acid and soybean oil fatty acid.
The active energy ray-curable ink for offset lithography of the present invention can form a cured coating film by irradiating active energy rays after printing on a substrate.
Examples of the active energy rays include ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. In the case of using ultraviolet rays as the active energy rays, the ultraviolet rays may be efficiently subjected to a curing reaction by irradiation under an inert gas atmosphere such as nitrogen or an air atmosphere.
As the source of the ultraviolet light, ultraviolet lamps are generally used from the viewpoints of practicality and economy. Specifically, a germicidal lamp, a fluorescent lamp for ultraviolet rays, a high-pressure mercury lamp for copying, a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, an electrodeless lamp, a carbon arc, a xenon lamp, a gallium lamp, a metal halide lamp, sunlight, an ultraviolet light emitting diode (UV-LED), and the like can be cited.
The active energy ray-curable ink for offset lithography of the present invention may be used without a solvent, or may be used with an appropriate solvent as required. The solvent is not particularly limited as long as it does not react with the above components, and may be used alone or in combination of 2 or more.
The active energy ray-curable ink for offset lithography of the present invention can be produced by the same method as in the prior art, for example, by kneading, mixing and adjusting the components of the ink composition, such as the pigment, the resin, the acrylic monomer or oligomer, the polymerization inhibitor, the sensitizer such as the initiator and the amine compound, and other additives, using a kneader, a three-roll mill, a attritor, a sand mill, a frame mixer, and the like at a temperature of between room temperature and 100 ℃.
(method for producing cured ink product, printed matter)
The ink cured product of the present invention is characterized in that offset printing is performed on a substrate using an active energy ray-curable ink for offset lithography, and the printed ink is cured using active energy rays.
(printing method)
As described above, the active energy ray-curable ink for offset lithography according to the present invention can be preferably used for an offset lithography system in which offset printing (offset printing using a fountain solution or waterless offset printing without a fountain solution) and a transfer (offset) system in which an ink attached to the plate is transferred to an intermediate transfer body such as a blanket and then printed on a printing target are combined.
The ink composition is applicable to a lithographic offset printing system in which the ink composition has a relatively high viscosity of 5 to 100 Pa.s, and is supplied from an ink fountain of a lithographic printing press to an inking portion of a plate surface via a plurality of rollers, and in a lithographic printing system using a fountain solution, the fountain solution is supplied to a non-inking portion to repel the ink composition, thereby forming an image on paper.
In lithographic printing using a fountain solution, the emulsion balance between the ink and the fountain solution is important, and high-speed printing compatibility with emulsion resistance is also required for the ink. If the emulsion amount of the ink is too high, the ink tends to be stained in the non-inking portion, or the emulsified ink is wound around the water bar roller to cause printing defects such as flying ink (running) and accumulation of the ink on a blanket outside the paper feed. If the amount of emulsion is small, contamination of the non-inking part called a plate (screen) becomes remarkable at the time of printing with a small pattern, and stable printing becomes difficult.
From this viewpoint, in the active energy ray-curable ink for offset lithography of the present invention, the acid value of the resin or monomer used in the ink is preferably in the range of 0 to 20.0, more preferably in the range of 0.0 to 10.0. If the acid value of the resin or monomer is high, the ink tends to be emulsified, and when the supply amount of the fountain solution is increased during printing, the concentration of the printed matter is reduced, or the emulsified ink tends to adhere to the non-inked portion of the plate subjected to hydrophilization treatment, so that contamination occurs in the non-inked portion of the printed matter.
[ example ]
Hereinafter, the present invention will be described specifically with reference to examples and comparative examples.
Example 1
(method for producing active energy ray-curable ink for offset lithography)
As the copolymer (A), 15 parts by mass of the copolymer (A-1) which is a polymer of the polymerization components shown in Table 1 and 55 parts by mass of dipentaerythritol hexaacrylate were mixed, and the inside of the reaction vessel was heated to 110℃to prepare a varnish (V1).
70 parts by mass of the varnish (V1), 10 parts by mass of an acyl phosphine oxide-based photopolymerization initiator Omnirad TPO (2, 4, 6-trimethylbenzoyl diphenyl phosphine oxide, manufactured by IGM Co.), 5 parts by mass of Omnirad EMK (4, 4' -diethylaminobenzophenone, manufactured by IGM Co.) were mixed at 60℃for 3 hours, 15 parts by mass of Raven 1060Ultra (manufactured by BIRLA CARBON Co.) as CARBON black was added thereto, and the mixture was stirred by a stirrer (a single-shaft dissolver), and then kneaded by a three-roll mill to obtain an active energy ray-curable offset ink 1.
[ Table 1 ]
[ Table 2 ]
In tables 1 and 2, the numerical values are parts (solid components), and the blank indicates that they are not blended. In addition, abbreviations are as follows.
Polymeric component (a): polyfunctional (meth) acrylate compound having 2 to 6 functional groups
Polymerization component (b): aryl (meth) acrylate compound
Polymerization component (c): styrene compound
Polymerization component (d): compound containing polymerizable unsaturated bond having hydrophilic group
Polymeric component (e): (meth) acrylate compound having nitrogen-containing heterocyclic group
Polymerization component (f): (meth) acrylate compound having alkylamino group
[ examples 2 to 6 and comparative examples 1 to 8: preparation of active energy ray-curable offset inks 2 to 6 and 9 to 16
Varnishes (V2 to V6) and (VR 1 to 8) were prepared for the resins A2 to 6 and AR1 to 8 in the same manner as in example 1.
Next, the ink was liquefied by the same method, and active energy ray-curable offset inks 2 to 6 and inks 9 to 16 were obtained.
Examples 7 to 8: preparation of active energy ray-curable offset inks 7 to 8
In a flask, 7.5 parts by mass of resin A2 and 7.5 parts by mass of DAP or ISO DAP manufactured by Osaka Soda were mixed, 55 parts by mass of dipentaerythritol hexaacrylate was mixed, and the inside of the reaction vessel was heated to 110℃to prepare varnishes (V7-8).
The ink liquefaction was performed in the same manner as in example 1 to obtain active energy ray-curable offset inks 7 to 8.
Comparative examples 9 to 12: preparation of active energy ray-curable offset inks 17 to 20
The active energy ray-curable offset inks 17 to 20 were obtained by dissolving the known resins shown in table 3 in the respective ratios in a flask to prepare varnishes and liquefying the inks in the same manner.
Example 9: preparation of active energy ray-curable offset ink (21)
20 parts by mass of resin (A2) and 50 parts by mass of ditrimethylolpropane tetraacrylate (DTMPTA) Miramer M410 (MIWON Co.) were mixed in a flask, and the inside of the reaction vessel was heated to 110℃to prepare a varnish (V9). The ink liquefaction was performed in the same manner as in example 1 to obtain an active energy ray-curable offset ink 21.
Examples 10 to 11: preparation of active energy ray-curable offset inks 22 to 23
10 parts by mass of resin A2 and 10 parts by mass of DAP or ISO DAP manufactured by Osaka Soda were mixed in a flask, 50 parts by mass of ditrimethylolpropane tetraacrylate was mixed, and the inside of the reaction vessel was heated to 110℃to prepare varnishes (V10-11).
The ink liquefaction was performed in the same manner as in example 1 to obtain active energy ray-curable offset inks 22 to 23.
[ example 12: preparation of active energy ray-curable offset ink 24
In a flask, 23 parts by mass of resin (A2) and 47 parts by mass of trimethylolpropane Ethylene Oxide (EO) -modified triacrylate (TMP (EO) 3 TA) MiramerM3130 (manufactured by MIWON Co.) were mixed, and the inside of the reaction vessel was heated to 110℃to prepare a varnish (V12). The ink liquefaction was performed in the same manner as in example 1 to obtain an active energy ray-curable offset ink 24.
Examples 13 to 14: preparation of active energy ray-curable offset inks 25 to 26
In a flask, 11.5 parts by mass of A2 and 11.5 parts by mass of DAP or ISO DAP manufactured by Osaka Soda, 47 parts by mass of trimethylolpropane Ethylene Oxide (EO) -modified triacrylate were mixed, and the inside of the reaction vessel was heated to 110℃to prepare varnishes (V13-14).
The ink liquefaction was performed in the same manner as in example 1 to obtain active energy ray-curable offset inks 25 to 26.
Examples 15 to 17: preparation of active energy ray-curable offset inks 27 to 29
15 parts by mass of the resin (A2) and 53 parts by mass of dipentaerythritol hexaacrylate were mixed in the same manner as in example 1, and the inside of the reaction vessel was heated to 110℃to prepare varnish V15. 68 parts by mass of the varnish, 10 parts by mass of an acyl phosphine oxide-based photopolymerization initiator Omnirad TPO (2, 4, 6-trimethylbenzoyl diphenyl phosphine oxide, manufactured by IGM Co.), 5 parts by mass of Omnirad EMK (4, 4' -bis-diethylaminobenzophenone, manufactured by IGM Co.), and 2 parts by mass of each extender pigment shown in Table 6 were mixed at 60℃for 3 hours, 15 parts by mass of Raven 1060Ultra (manufactured by BIRLA CARBON Co.) as CARBON black was added, and the mixture was stirred by a stirrer (single-shaft dissolver), and then kneaded by a three-roll mill, thereby obtaining active energy ray-curable offset inks 27 to 29.
The active energy ray-curable offset inks obtained in the above examples and comparative examples were used to carry out the following evaluation. The ink viscosities of the obtained inks 1 to 29 were confirmed to be 25pa.s at 25 ℃.
Using the obtained active energy ray-curable offset ink, paper separation was evaluated by a printer.
Evaluation item 1: paper peeling off
As the ultraviolet irradiation apparatus, a LITHRONE G40 manufactured by KOMORI Corporation, which is mounted with a water-cooled metal halide lamp manufactured by EYE GRAPHICS (output 160W/cm, 3 sheets were used), was used, the gap between the ink fountain and the ink fountain roller was adjusted to 2 to 3 μm, the solid density of the solid portion of the pattern was uniformly density-matched with an ink density of 1.7 (measured with a SpectroEye densitometer manufactured by X-Rite), and offset printing was performed at a printing speed of 15000 sheets per hour. As the printing paper, OK TOPCOAT Plus (57.5 kg, size A) manufactured by prince paper manufacturing company was used. The fountain solution to be supplied to the plate surface was an aqueous solution obtained by mixing 98% by mass of tap water with 2% by mass of an etching solution (FST-700, manufactured by DIC Co.). At this time, the degree of paper peeling of the printed matter was visually evaluated in the following 5 stages.
(evaluation criterion)
5: no paper peeling was observed at all in the printed matter.
4: paper peeling was slightly observed in the print.
3: the paper peeling was observed in the printed matter to some extent, but to the extent that the quality was not affected.
2: paper peeling was observed in the print.
1: the printed matter was significantly peeled off from the paper.
Evaluation item 2: ink fluidity ]
The fluidity of the ink was measured by the spring Meter method (parallel plate viscometer) in accordance with the method specified in JIS K5101 and 5701, and the characteristic that the ink sandwiched between 2 parallel plates placed horizontally was Spread into concentric circles by the weight of the load plate (115 g) was observed with time, and the Spread Diameter of the ink after 60 seconds was measured as Diameter value (DM [ mm ]). In the present evaluation item, ink accumulation occurs on the printer in a composition having DM of less than 25mm, and a problem in terms of printing suitability such as defective transfer between ink rollers is likely to occur.
If DM is 30mm or more, it is considered good.
(evaluation criterion)
5:40mm or more
4: less than 35-40 mm
3: less than 30-35 mm
2: less than 25-30 mm
1: less than 25mm
Evaluation item 3: curability ]
Regarding curability, the degree of scratch was confirmed by a nail scratch method immediately after ultraviolet irradiation on the surface of the solid portion of the printed matter produced in the order of evaluation item 1, and visual evaluation was performed in the following 5 stages. In the composition in which scratches are formed on the ink-cured film by scraping with nails, the printed matter is easily damaged in each step of cutting, making a box, and conveying the printed matter.
(evaluation criterion)
5: no scratch was generated at all during nail scratch, and curability was optimal.
4: a slight scratch was slightly observed in the nail scratch.
3: scratches were observed in nail scratch, but at a level that could be used.
2: scratch is generated during nail scratch, and it cannot be said that curability is sufficient.
1: scratches were simply generated in nail scratch, and curability was the worst.
Evaluation item 4: flying ink (sizing)
An active energy ray-curable offset ink (1.35 ml) was applied to the ocean refiner, and OK TOPCOAT Plus (57.5 kg, A size) was set at the lower and rear parts of the machine, respectively, and rotated at 1200rpm for 3 minutes. Thereafter, according to the amount of ink splashed on the set paper, the flying ink was visually evaluated in the following 5 stages.
(evaluation criterion)
5: no splashing at all.
4: although splattered, there is little.
3: although splatter, it is sufficient in quality to print.
2: the amount of splash is large.
1: and significant splatter.
Tables 3 to 7 show the evaluation results of the active energy ray-curable offset inks.
[ Table 3 ]
[ Table 4 ]
[ Table 5 ]
[ Table 6 ]
[ Table 7 ]
The values in tables 3 to 7 are mass% (solid content). The raw materials and abbreviations shown in the tables are shown below.
Raven 1060Ultra: carbon black, manufactured by BIRLA Co
Omnirad TPO:2,4, 6-trimethylbenzoyl diphenyl phosphine oxide, number average molecular weight 418.5, manufactured by IGM Co
Omnirad EMK:4,4' -bis (diethylamino) benzophenone, number average molecular weight 324.5, manufactured by IGM Co
AR-9: daiso dap A: diallyl phthalate resin having a weight average molecular weight of 5.5 ten thousand: manufactured by Osaka Soda Co., ltd
AR-10: daiso isocap: diallyl isophthalate resin having a weight average molecular weight of 5 ten thousand: manufactured by Osaka Soda Co., ltd
AR-11: variplus AP: polyketone oligomer manufactured by Evonic Co
AR-12: laropal a81: urea-aldehyde resin, manufactured by BASF corporation
HI-FILLER#5000PJ: talc based on hydrous magnesium silicate, manufactured by Songcun industries Co., ltd
White and brilliant TDD: calcium carbonate, manufactured by Baishi Industrial Co Ltd
Magnesium carbonate TT: basic magnesium carbonate, manufactured by NIKAI salt Co., ltd
DPHA: miramer M600: dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate mixture (DPHA), manufactured by MIWON Co
DTMPTA: miramer M410: trimethylolpropane tetraacrylate, MIWON Co
TMP (EO) 3TA: miramer M3130: trimethylol propane ethylene oxide modified triacrylate, manufactured by MIWON Co
The active energy ray-curable ink for offset lithography of the present invention does not cause paper peeling even when the substrate is paper, has excellent curability and excellent fluidity, and can suppress flying ink.
Claims (6)
1. An active energy ray-curable ink for offset lithography, characterized by comprising a copolymer (A) and a (meth) acrylate compound (B), wherein the copolymer (A) comprises a polymer containing, as an essential polymerization component,
the components are as follows:
5 to 70% by mass of (a) a polyfunctional (meth) acrylate compound having 2 to 6 functional groups;
0.1 to 50 mass% of (b) an aryl (meth) acrylate compound;
5 to 40 mass% of (c) a styrene compound;
0.1 to 10% by mass of (d) a compound having a hydrophilic group and containing a polymerizable unsaturated bond;
0.1 to 10% by mass of (e) a (meth) acrylate compound having a nitrogen-containing heterocyclic group;
0.1 to 10% by mass of (f) a (meth) acrylate compound having an alkylamino group,
wherein the total amount of (a) to (f) is 100% by mass,
the weight average molecular weight of the copolymer (A) is 5000-100000,
The copolymer (A) has a PDI of 3 to 35 in molecular weight,
the (meth) acrylate compound (B) is not diallyl phthalate.
2. The active energy ray-curable ink for offset lithography according to claim 1, wherein the acid value of the copolymer (a) is 1mg/KOH/g to 40mg/KOH/g.
3. The active energy ray-curable ink for offset lithography according to claim 1 or 2, wherein the weight ratio of the copolymer (a) to the (meth) acrylate compound (B) is 5: 65-30: 40.
4. The active energy ray-curable ink for offset lithography according to claim 1 or 2, wherein at least 1 selected from the group consisting of talc, magnesium carbonate and calcium carbonate is contained as the extender pigment (C).
5. The active energy ray-curable ink for offset lithography according to claim 3, wherein at least 1 selected from the group consisting of talc, magnesium carbonate and calcium carbonate is contained as the extender pigment (C).
6. A printed matter comprising the cured product of the active energy ray-curable ink for offset lithography according to any one of claims 1 to 3 on a substrate.
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| CN105102493A (en) * | 2013-03-29 | 2015-11-25 | 新日铁住金化学株式会社 | Polyfunctional (meth)acrylic acid ester copolymer, and curable resin composition and cured product thereof |
| CN105209942A (en) * | 2013-05-15 | 2015-12-30 | 柯尼卡美能达株式会社 | Phase difference film, polarization plate, and liquid crystal display device |
| CN108350125A (en) * | 2015-11-20 | 2018-07-31 | 旭化成株式会社 | Metha crylic resin, Methacrylic resin composition, film, manufacturing method |
| CN110337472A (en) * | 2017-03-07 | 2019-10-15 | 东丽株式会社 | The manufacturing method of active energy ray curable lithographic printing ink and the printed article using it |
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| JP5477995B1 (en) | 2013-03-12 | 2014-04-23 | サカタインクス株式会社 | Active energy ray-curable offset printing ink composition |
| WO2014156812A1 (en) | 2013-03-27 | 2014-10-02 | Ｄｉｃグラフィックス株式会社 | Active energy ray-curable offset ink composition |
| JP6331242B1 (en) | 2017-01-31 | 2018-05-30 | 荒川化学工業株式会社 | Resin, varnish composition, offset printing ink and printed matter |
| JP7226071B2 (en) | 2018-05-07 | 2023-02-21 | 荒川化学工業株式会社 | Resins, varnish compositions, printing inks and printed matter |
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| CN105102493A (en) * | 2013-03-29 | 2015-11-25 | 新日铁住金化学株式会社 | Polyfunctional (meth)acrylic acid ester copolymer, and curable resin composition and cured product thereof |
| CN105209942A (en) * | 2013-05-15 | 2015-12-30 | 柯尼卡美能达株式会社 | Phase difference film, polarization plate, and liquid crystal display device |
| CN108350125A (en) * | 2015-11-20 | 2018-07-31 | 旭化成株式会社 | Metha crylic resin, Methacrylic resin composition, film, manufacturing method |
| CN110337472A (en) * | 2017-03-07 | 2019-10-15 | 东丽株式会社 | The manufacturing method of active energy ray curable lithographic printing ink and the printed article using it |
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