Classifications

• • 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
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/10—Esters
  • C08F20/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• • 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
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/67—Unsaturated compounds having active hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/67—Unsaturated compounds having active hydrogen
  • C08G18/68—Unsaturated polyesters
• • 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

Definitions

• the present invention relates to a composition that can be suitably used for printing ink applications, a printing ink using the same, and a printed material obtained by printing the printing ink.
• Active energy ray-curable printing inks are excellent in workability because they can be instantaneously cured by irradiation with energy rays such as ultraviolet rays, and basically they are used without a solvent, so they have advantages such as relatively low environmental impact. Besides paper printing, it is used for various applications such as plastic packaging materials. However, on the other hand, the leveling property of the printing surface is low due to the above-mentioned immediate curing property so that the gloss is difficult to appear, and the adhesion to the printing surface is low compared to oil-based ink. There is also a need for effective solutions to these issues.
• binder resins for active energy ray-curable printing inks include diallyl phthalate resins which are excellent in compatibility with reactive diluents such as dipentaerythritol polyacrylate, and rosin-modified (meth) acrylate resins which are excellent in substrate adhesion. Although known, issues with print surface gloss remained in any of the techniques.
• the problem to be solved by the present invention is to provide a printing ink excellent in printed surface gloss.
• the inventors of the present invention conducted intensive studies to solve the above problems, and as a result, by blending a composition containing an acid group-containing urethane (meth) acrylate resin and a metal complex into a printing ink, the flowability of the printing ink becomes As a result, it has been found that an improved, high-gloss printed surface can be obtained, and the present invention has been completed.
• the present invention relates to a composition containing an acid group-containing urethane (meth) acrylate resin (A) and a metal complex (B).
• the invention further relates to a printing ink comprising the composition.
• the present invention further relates to a printed material obtained by printing the printing ink.
• the printing ink which is excellent in printing surface gloss, the printed matter using this, and a composition useful as said printing ink raw material can be provided.
• the composition of the present invention contains an acid group-containing urethane (meth) acrylate resin (A) and a metal complex (B).
• the acid group-containing urethane (meth) acrylate resin (A) may have a urethane bond site in the molecular structure and an acid group such as a carboxy group, and the other specific structure is not particularly limited.
• the (meth) acrylate resin refers to a resin having an acryloyl group, a methacryloyl group, or both in the molecule.
• a (meth) acryloyl group means one or both of an acryloyl group and a methacryloyl group
• a (meth) acrylate is a general term for an acrylate and a methacrylate.
• polyisocyanate compound (a1) examples include aliphatic diisocyanate compounds such as butane diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate; norbornane diisocyanate, isophorone Alicyclic diisocyanate compounds such as diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate; tolylene diisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, diphenylmethane diisocyanate, aromatic diisocyanate compounds such as 1,5-naphthalene diisocyanate; Polyisocyanate having a repeating structure represented by the following structural formula (1) Compound; these isocyanurate modified product, a biuret modified product, and allophanate modified compounds and the like
• each R 1 independently represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.
• R 2 each independently represents an alkyl group having 1 to 4 carbon atoms, or a bonding point which is linked to the structural moiety represented by the structural formula (1) via a methylene group marked with an asterisk (*).
• l is an integer of 0 or 1 to 3
• m is an integer of 1 or more.
• the polyisocyanate compounds (a1) it is possible to obtain a printing ink which is excellent in fluidity and gloss of the printing surface, and is also excellent in general printability such as misting resistance and emulsification suitability. It is preferable to essentially use a polyisocyanate compound having a molecular structure represented by the above, or a polyisocyanate compound having an average functional group number of 3 or more, such as isocyanurate-modified products of various diisocyanate compounds.
• the proportion of the polyisocyanate compound having an average functional group number of 3 or more in the polyisocyanate compound (a1) is preferably 70% by mass or more, and more preferably 90% by mass or more.
• the raw material diisocyanate compound is preferably an aliphatic or alicyclic diisocyanate compound, and an aliphatic diisocyanate compound is particularly preferable.
• hydroxy (meth) acrylate compound (a2) examples include aliphatic hydroxy mono (meth) acrylate compounds such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and hydroxybutyl acrylate; glycerin di (meth) acrylate, Aliphatic hydroxy poly (meth) acrylate compounds such as trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate; 4-hydroxyphenyl acrylate, ⁇ -hydroxyphenethyl acrylate , 4-hydroxyphenethyl acrylate, 1-phenyl-2-hydroxyethyl acrylate, 3-hydroxy-4-acetylphenyl acrylate, 2-hydroxy-3- Aromatic hydroxy mono (meth) acrylate compounds such as phenoxypropyl acrylate; various hydroxy (meth)
• the above-mentioned fat is excellent because it is excellent in fluidity and gloss on the printing surface, and is also excellent in general printability such as misting resistance and emulsification suitability.
• Group hydroxy mono (meth) acrylate compounds, the above-mentioned aliphatic hydroxy poly (meth) acrylate compounds, and polyoxyalkylene modified products or lactone modifications thereof are preferable, lactone modified aliphatic hydroxy (meth) acrylate compounds are more preferable, and lactone modified Particular preference is given to aliphatic hydroxy mono (meth) acrylate compounds.
• denatured aliphatic hydroxy mono (meth) acrylate compound to the said hydroxy (meth) acrylate compound (a2) is 70 mass% or more, and it is more preferable that it is 90 mass% or more.
• the acid group-containing hydroxy compound (a3) has an acid group such as a carboxy group and a hydroxy group in its molecular structure, the number of carboxy groups and hydroxy groups and other specific structures are not particularly limited.
• the acid group-containing hydroxy compounds (a3) may be used alone or in combination of two or more. Among them, an aliphatic compound is preferable because a printing ink having excellent fluidity and print surface gloss can be obtained, and an aliphatic hydrocarbon having 2 to 20 carbon atoms having 1 to 3 carboxy groups, hydroxy Compounds having 1 to 3 groups are more preferred.
• Such compounds include, for example, glycolic acid, lactic acid, hydroxybutanoic acid, hydroxypentanoic acid, hydroxyhexanoic acid, hydroxyheptanoic acid, hydroxyoctanoic acid, hydroxynonanoic acid, hydroxydecanoic acid, hydroxydodecanoic acid, hydroxy Monohydroxy compounds such as tetradecanoic acid, hydroxyhexadecanoic acid, hydroxyheptadecanoic acid, hydroxyoctadecanoic acid (hydroxystearic acid), ricinoleic acid, etc.
• Glyceric acid 2- (hydroxymethyl) -3-hydroxypropionic acid, 2- (dihydroxymethyl) Dihydroxy compounds such as propionic acid, dimethylol propionic acid, 3, 3-dimethylol propionic acid; trihydroxy compounds such as 3-hydroxy-2, 2-bis (hydroxymethyl) propionic acid Compounds, and the like.
• the acid group-containing urethane (meth) acrylate resin (A) is a reaction raw material other than the polyisocyanate compound (a1), the hydroxy (meth) acrylate compound (a2) and the acid group-containing hydroxy compound (a3) May be used in combination.
• As another reaction raw material polyol compounds other than the said hydroxy (meth) acrylate compound (a2) and the said acid group containing hydroxy compound (a3) etc. are mentioned, for example.
• polyol compound examples include aliphatic polyol compounds such as ethylene glycol, propylene glycol, butanediol, hexanediol, glycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol and dipentaerythritol; and aromatics such as biphenol and bisphenol Polyol compounds; (Poly) oxyalkylene chains in which (poly) oxyethylene chains such as (poly) oxyethylene chains, (poly) oxypropylene chains, (poly) oxytetramethylene chains are introduced into the molecular structures of the various polyol compounds Modified products; lactone modified products in which a (poly) lactone structure is introduced into the molecular structure of the various polyol compounds, and the like.
• aliphatic polyol compounds such as ethylene glycol, propylene glycol, butanediol, hexanediol, g
• the polyisocyanate compound (a1) in the reaction raw material of the acid group-containing urethane (meth) acrylate resin (A) is preferably 70% by mass or more, and more preferably 90% by mass or more.
• the method for producing the acid group-containing urethane (meth) acrylate resin (A) is not particularly limited, and in general, it can be produced by the same method as a general urethane (meth) acrylate resin.
• the reaction ratio of each component, the reaction order, and the like are appropriately adjusted according to the desired resin design and resin performance, and are not particularly limited.
• each reaction raw material is heated to a temperature of 20 to 120 ° C. at a ratio that the hydroxyl group in the reaction raw material is in the range of 0.9 to 1.1 mol with respect to 1 mol of isocyanate group in the reaction raw material. Methods are included.
• known and conventional urethanization catalysts such as zinc octylate, various antioxidants, polymerization inhibitors and the like may be used.
• the acid value of the acid group-containing urethane (meth) acrylate resin (A) is preferably in the range of 1 to 50 mg KOH / g, since a printing ink having more excellent fluidity and gloss on the printed surface can be obtained.
• the range of 40 mg KOH / g is more preferable, and the range of 3 to 35 mg KOH / g is particularly preferable.
• the acid value of the resin is a value measured by the neutralization titration method of JIS K 0070 (1992).
• the mass average molecular weight (Mw) of the acid group-containing urethane (meth) acrylate resin (A) is 1,000 from the viewpoint of obtaining a printing ink which is further excellent in fluidity and gloss of the printing surface when used for printing ink applications. It is preferably in the range of ⁇ 25,000, and more preferably in the range of 1,000 to 10,000.
• the molecular weight of the resin is a value measured by gel permeation chromatography (GPC) under the following conditions.
• the metal complex (B) is, for example, aluminum trialkylate such as aluminum triethylate aluminum tripropylate, aluminum dipropylate monobutyrate, aluminum tributyrate etc; aluminum acetyl acetate dipropylate, aluminum acetyl acetate dibutyrate, Aluminum alkyl acetoacetates such as aluminum triacetyl acetate, aluminum ethyl acetoacetate dipropylate, aluminum tris ethyl acetoacetate, aluminum octadecyl acetoacetate dipropylate; titanium tetraalkylates such as titanium tetrapropylate, titanium tetrabutyrate; titanium bis Titanium alkylacetoacetates such as (acetyl acetate) dipropylate; Zirconium tetra alkylate such as benzalkonium tetrabutylate and the like.
• aluminum trialkylate such as aluminum triethylate aluminum tripropylate, aluminum di
• ALD aluminum organic compound series
• ASBD aluminum organic compound series
• AIPD AIPD
• PADM aluminum ethoxide
• ALD-TR aluminum organic compound series
• ALD aluminum organic compound series
• ALCH-TR aluminum organic compound series
• Prenact series (“AL-M”, “TTS” ) “Orgatics” series (“AL-3001”, “AL-3100”, “AL-3200”, “AL-3215”, “TA-8”, “TA-21”, TA-23, TA-30, TC-100, TC-401, TC-710, TC-750, ZA- 5 ",” ZA-65 “,” AC-150 “,” ZC-540 “), and the like.
• the said metal complex (B) may be used individually by 1 type, and may use 2 or more types together.
• the compounding quantity of the said metal complex (B) can be suitably adjusted according to the desired ink performance etc., in particular, it is highly fluid, it is excellent in the glossiness of a printing surface, and other performances, such as misting resistance and emulsification suitability.
• the printing ink is sufficiently high, it is preferably in the range of 0.5 to 20 parts by mass, preferably 1 to 15 parts by mass, per 100 parts by mass of the acid group-containing urethane (meth) acrylate resin (A). The range is particularly preferred.
• the composition of the present invention may contain other components such as other resin component (C) in addition to the acid group-containing urethane (meth) acrylate resin (A) and the metal complex (B).
• the other resin component (C) include various (meth) acrylate monomers (C1), urethane (meth) acrylate resins (C2) other than the component (A), and epoxy (meth) acrylate resins (C3) And polyester (meth) acrylate resin (C4), ketone resin (C5), diallyl phthalate (DAP) resin (C6) and the like.
• the effect of the present invention that is, by using a composition containing an acid group-containing urethane (meth) acrylate resin (A) and a metal complex (B) for printing ink applications, the flowability is high and the gloss of the printing surface is excellent.
• the other resin component (C) may be any of various resin materials that can be used for printing ink, and is not particularly limited, but some specific examples are listed below.
• Examples of the (meth) acrylate monomer (C1) include aliphatic mono (meth) acrylate compounds such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate and butyl (meth) acrylate; cyclohexyl (meth) acrylate ) Alicyclic mono (meth) acrylate compounds such as acrylate, isobornyl (meth) acrylate and adamantyl mono (meth) acrylate; heterocyclic mono (meth) acrylate compounds such as glycidyl (meth) acrylate and tetrahydrofurfuryl acrylate; benzyl Aromatic mono (meth) acrylate compounds such as (meth) acrylates and phenoxy (meth) acrylates; hydroxyl group-containing mono (hydroxyethyl (meth) acrylates, hydroxypropyl (meth) acrylates, etc.
• Aliphatic di (meth) acrylate compounds such as ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butanediol di (meth) acrylate, hexanediol di (meth) acrylate and neopentyl glycol di (meth) acrylate
• Alicyclic di (meth) acrylate compounds such as norbornane di (meth) acrylate, norbornane dimethanol di (meth) acrylate, dicyclopentanyl di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate; biphenol Aromatic di (meth) acrylate compounds such as di (meth) acrylates and bisphenol di (meth) acrylates; polyoxyethylene chains, polyoxyprosts in the molecular structures of the various di (meth) acrylate compounds Polyoxyalkylene-modified di (meth) acrylate compounds into which a poly
• Aliphatic tri (meth) acrylate compounds such as trimethylolpropane tri (meth) acrylate and glycerin tri (meth) acrylate; pentaerythritol tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, dipentaerythritol tri (meth) A hydroxyl group-containing tri (meth) acrylate compound such as acrylate; a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain, or a polyoxytetramethylene chain introduced into the molecular structure of each of the various tri (meth) acrylate compounds Polyoxyalkylene-modified tri (meth) acrylate compounds; Lactone-modified tri (meth) acrylate compounds in which a (poly) lactone structure is introduced into the molecular structures of the various tri (meth) acrylate compounds;
• Tetrafunctional or higher aliphatic poly (meth) acrylate compounds such as pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate; dipentaerythritol tetra (meth) acrylate, dipentaerythritol And tetrafunctional or higher hydroxyl group-containing poly (meth) acrylate compounds such as pentaerythritol penta (meth) acrylate; polyoxyethylene chains, polyoxypropylene chains, polyoxytetramethylenes in the molecular structures of the various poly (meth) acrylate compounds; And the like.
• Examples of the urethane (meth) acrylate resin (C2) include those obtained by reacting various polyisocyanate compounds, hydroxyl group-containing (meth) acrylate compounds, and various polyol compounds as needed. Specific examples of these reaction raw materials include those exemplified in the explanation of the acid group-containing urethane (meth) acrylate resin (A).
• Examples of the epoxy (meth) acrylate compound (C3) include bisphenol-type epoxy resins and (meth) acrylic esters of epoxy group-containing compounds such as trimethylolpropane triglycidyl ether.
• the epoxy (meth) acrylate compound (C3) may have a polyoxyalkylene chain in the molecular structure.
• the polyester (meth) acrylate resin (C4) may be a (meth) acrylate resin having a polyester structural site in its molecular structure, and may be an alkyd resin containing fats and oils or fatty acids in part of the reaction raw material, or one of the reaction raw materials It may be a urethane-modified type containing polyisocyanate in part.
• the compounding amount of the other resin component (C) can be appropriately adjusted according to the desired ink performance etc., but the effect of the present invention can be exhibited more effectively.
• Acid group-containing urethane (meth) acrylate resin (A) and metal complex (B) with respect to the total of the metal complex (B) and the other resin component (C) Is preferably in the range of 0.5 to 20% by mass, and more preferably in the range of 1 to 10% by mass.
• the composition of the present invention can be suitably used mainly for active energy ray-curable printing inks, and preferably contains a photopolymerization initiator according to the active energy ray to be irradiated.
• a photopolymerization initiator for example, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2- (dimethylamino) -2- Alkylphenone photopolymerization initiators such as [(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone; 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide etc.
• IRGACURE series (“IRGACURE 127”, “IRGACURE 184”, “IRGACURE 250”, “IRGACURE 270”, “IRGACURE 290”, “IRGACURE 369 E”, “IRGACURE 379 EG”, manufactured by BASF Corporation), IRGACURE 500 “,” IRGACURE 651 “,” IRGACURE 754 “,” IRGACURE 819 “,” IRGACURE 907 “,” IRGACURE 1173 “,” IRGACURE 2959 “,” IRGACURE MBF “,” IRGACURE TPO “,” IRGACURE OXE 01 “,” IRGACURE OXE 02 “ “OMNIRAD” manufactured by IGM RESINS (“OMNIRAD 184”, “OMNIRAD 250”, “OMNIRAD 369”, “OMNIRAD 369E”, “OMNIRAD 651”, “OMNIRAD 907FF”, “OMNIRAD 1173”), “DAIDO UV-CURE” series manufactured by D
• photopolymerization initiators are preferably used in a range of about 0.05 to 20 parts by mass in 100 parts by mass of the total of the composition.
• the composition of the present invention may contain a photosensitizer in combination with the above-mentioned polymerization initiator.
• the photosensitizer include amine compounds such as aliphatic amines, ureas such as o-tolylthiourea, and sulfur compounds such as sodium diethyl dithiophosphate and s-benzylisothyuronium-p-toluenesulfonate. .
• These photosensitizers are preferably used in the range of about 0.1 to 10 parts by mass in 100 parts by mass of the total of the composition.
• composition of the present invention may further comprise a pigment, a dye, an extender, an organic or inorganic filler, an organic solvent, an antistatic agent, an antifoamer, a viscosity modifier, a polymerization inhibitor, a light stabilizer, a weathering stabilizer, and a heat resistant stabilizer.
• You may contain various additives which normal printing ink contains, such as an agent, an ultraviolet absorber, an antioxidant, a leveling agent, a pigment dispersant, and a wax.
• the pigment examples include publicly known and publicly used organic pigments for coloring, such as, for example, organic pigments for printing ink disclosed in "organic pigment handbook (author: Hashimoto Isao, publishing office: color office, 2006 first edition)" Soluble azo pigments, insoluble azo pigments, condensed azo pigments, metal phthalocyanine pigments, metal free phthalocyanine pigments, quinacridone pigments, perylene pigments, perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, thioindigo pigments, anthraquinone Based pigments, quinophthalone pigments, metal complex pigments, diketopyrrolopyrrole pigments, carbon black pigments, and other polycyclic pigments can be used.
• the addition amount of the pigment varies in optimum value depending on the kind of the pigment and the like, but is preferably in the range of 5 to 30 parts by mass with respect to 100 parts by mass of the
• extender pigment examples include titanium oxide, claphyte, zinc, lime carbonate powder, precipitated calcium carbonate, gypsum, clay, silica powder, diatomaceous earth, talc, kaolin, alumina white, barium sulfate, aluminum stearate, magnesium carbonate, Barite powder, glass beads, etc. are raised.
• the addition amount of these extender pigments varies in optimum value depending on the kind of pigment and the like, but is preferably in the range of 0.1 to 20 parts by mass with respect to 100 parts by mass in total of the composition.
• the blending ratio and the like of each component are not particularly limited, and the blending and the blending ratio can be appropriately adjusted according to the target printing application, performance and the like.
• Each of the components may be blended all at once, or may be split such as blending a part with the other components after preparing a premix first.
• the mixing method is not particularly limited, and examples thereof include a method of stirring and mixing with a mixer or the like, a method of using a three-roll mill, and a method of using a dispersing machine such as a bead mill.
• the printing ink of the present invention can be cured by irradiation with active energy rays.
• active energy ray include ionizing radiation such as ultraviolet ray, electron beam, alpha ray, beta ray, and gamma ray.
• light sources include germicidal lamps, fluorescent lamps for ultraviolet light, UV-LEDs, carbon arc, xenon lamps, high pressure mercury lamps for copying, medium or high pressure mercury lamps, super high pressure mercury lamps, electrodeless lamps, metal halide lamps, natural light etc.
• UV rays, electron beams by a scanning or curtain type electron beam accelerator, and the like can be mentioned.
• the printing ink of the present invention can be printed on various substrates such as paper and various plastic films.
• polypropylene films, polyethylene terephthalate films etc., food and beverages plastic film substrates for packaging materials such as cosmetics; aluminum foil, synthetic paper, and various other substrates conventionally used as printing substrates can be used as printing objects.
• the printing method of the printing ink of the present invention is not particularly limited, and for example, it can be printed by lithographic offset printing, letterpress printing, gravure printing, gravure offset printing, flexographic printing, screen printing and the like. Among these, it can be suitably used particularly in lithographic offset printing in which water is continuously supplied to the printing plate.
• Offset printing presses that continuously supply water are manufactured and sold by a number of printing press manufacturers, and include, for example, Heidelberg, Komori Corporation, Ryobi MHI Graphic Technology, Man Roland, KBA, etc.
• the present invention can be suitably used in a sheet-fed offset printing press using printing sheets in a sheet form, an offset rotary printing press using printing sheets in a reel form, and any sheet feeding method. More specifically, offset printing machines such as Heidelberg's Speedmaster series, Komori Corporation's Lithlon series, Ryobi MHI Graphic Technology's diamond series, etc. can be mentioned.
• Mw mass average molecular weight
• GPC gel permeation chromatography
• the mass average molecular weight (Mw) of the urethane (meth) acrylate resin (A-1) was 4,477, and the acid value was 11.2 mg KOH / g.
• the mass average molecular weight (Mw) of the urethane (meth) acrylate resin (A-4) was 4,135, and the acid value was 8.9 mg KOH / g.
• Examples 1 to 7 Preparation of Compositions (1) to (8) The components were blended in the proportions shown in Table 1 below, and stirred for 1 hour to obtain Compositions (1) to (8).
• the details of the metal complex are as follows.
• Example 9 to 21 and Comparative Example 1 Production of Printing Ink Each component is compounded in the proportions shown in Tables 3 to 5 below, stirred by a mixer (single-axis dissolver), and then drawn using a three-roll mill to print I got the ink.
• Example 14 after mix
• the resulting printing ink was subjected to various evaluations in the following manner. The results are shown in Tables 3 to 5.
• UV lamp light source The previously obtained color product was irradiated with ultraviolet (UV) light to cure the printing ink.
• a water-cooled metal halide lamp power 120 W / cm1 lamp
• an ultraviolet (UV) irradiator made by Eye Graphics Co., Ltd., attached with a cold mirror
• the display color is placed on the conveyor
• the printing ink was cured by passing immediately under the lamp (irradiation distance 11 cm) at a speed of 40 meters per minute.
• Gloss of Printed Surface The gloss value of the printed surface of the developed product after curing was measured with a 60 ° gloss meter (manufactured by BYK Garder GmbH) and evaluated in the following three steps. The higher the number, the better the gloss. (Evaluation criteria) A: Gloss 55 or more B: Gloss 45 or more 55 or less C C: Gloss 45 or less

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