CN110945044A - Composition and printing ink - Google Patents
Composition and printing ink Download PDFInfo
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- CN110945044A CN110945044A CN201880048598.8A CN201880048598A CN110945044A CN 110945044 A CN110945044 A CN 110945044A CN 201880048598 A CN201880048598 A CN 201880048598A CN 110945044 A CN110945044 A CN 110945044A
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- 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
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- 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
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- 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
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The present invention provides: a composition characterized by containing an acid group-containing urethane (meth) acrylate resin (A) and a metal complex (B), a composition characterized by containing a resin component (C) in addition to the acid group-containing urethane (meth) acrylate resin (A) and the metal complex (B), a printing ink obtained by using the composition, and a printed matter obtained by printing the printing ink. By blending the composition in a printing ink, a printing ink having high fluidity and excellent gloss of a printed surface can be formed.
Description
Technical Field
The present invention relates to a composition that can be suitably used for printing ink, printing ink using the composition, and printed matter obtained by printing the printing ink.
Background
Active energy ray-curable printing inks are excellent in handling properties because they can be cured instantaneously by irradiation with energy rays such as ultraviolet rays, and are relatively low in environmental load because they are used in a substantially solvent-free manner, and are used for paper printing, plastic packaging materials, and other applications because of the above-mentioned advantages. However, on the other hand, the above-mentioned curability also has the following problems: active energy ray-curable printing inks have unique problems such as low leveling property of the printed surface, difficulty in gloss, and low adhesion to the printed surface compared with oil-based inks, and effective solutions to these problems have been sought.
As binder resins for active energy ray-curable printing inks, diallyl phthalate resins having excellent compatibility with reactive diluents such as dipentaerythritol polyacrylate, rosin-modified (meth) acrylate resins having excellent adhesion to substrates, and the like are known, but problems relating to the gloss of the printed surface remain in any of the techniques.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 2010-100821
Disclosure of Invention
Problems to be solved by the invention
Accordingly, an object of the present invention is to provide a printing ink having excellent printing surface gloss.
Means for solving the problems
The inventors have made extensive studies to solve the above problems, and as a result, have found that: the present inventors have found that when a composition containing an acid group-containing urethane (meth) acrylate resin and a metal complex is blended in a printing ink, the fluidity of the printing ink is improved, and as a result, a high-gloss printed surface can be obtained, leading to completion of the present invention.
Namely, the present invention relates to a composition comprising: an acid group-containing urethane (meth) acrylate resin (A), and a metal complex (B).
The present invention also relates to a printing ink using the composition.
The present invention also relates to a printed matter obtained by printing the printing ink.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention can provide a printing ink having excellent printing surface gloss, a printed matter using the printing ink, and a composition useful as a raw material for the printing ink.
Detailed Description
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 molecular structure having a urethane bonding site and an acid group such as a carboxyl group, and other specific structures are not particularly limited. In the present invention, the (meth) acrylate resin means a resin having an acryloyl group, a methacryloyl group, or both of them in the molecule. The term (meth) acryloyl refers to one or both of acryloyl and methacryloyl, and the term (meth) acrylate refers to a generic term for acrylate and methacrylate.
Examples of the urethane (meth) acrylate resin (a) include a polyisocyanate compound (a1), a hydroxyl (meth) acrylate compound (a2), and an acid group-containing hydroxyl compound (a3) as essential reaction raw materials.
Examples of the polyisocyanate compound (a1) include: aliphatic diisocyanate compounds such as butane diisocyanate, hexamethylene diisocyanate, 2, 4-trimethylhexamethylene diisocyanate, and 2,4, 4-trimethylhexamethylene diisocyanate; alicyclic diisocyanate compounds such as norbornane diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, and hydrogenated diphenylmethane diisocyanate; aromatic diisocyanate compounds such as tolylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, diphenylmethane diisocyanate, and 1, 5-naphthalene diisocyanate; a polyisocyanate compound having a repeating structure represented by the following structural formula (1); and isocyanurate, biuret, allophanate modifications thereof. These may be used alone or in combination of 2 or more.
[ in the formula, R1Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. R2Each independently is an alkyl group having 1 to 4 carbon atoms or a bonding site connected to the structural site represented by the structural formula (1) via a methylene group marked with a symbol. l is 0 or an integer of 1 to 3, and m is an integer of 1 or more.]
Among the polyisocyanate compounds (a1), it is preferable to use a polyisocyanate compound having a molecular structure represented by the formula (1) or a polyisocyanate compound having an average functional group number of 3 or more, such as an isocyanurate-modified product of each diisocyanate compound, in order to obtain a printing ink having excellent fluidity and gloss of a printed surface and having excellent general printing suitability such as ink misting resistance and emulsion suitability. In particular, the ratio 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, more preferably 90% by mass or more. When the polyisocyanate compound is an isocyanurate-modified product, the diisocyanate compound as the raw material is preferably an aliphatic or alicyclic diisocyanate compound, and particularly preferably an aliphatic diisocyanate compound.
Examples of the hydroxyl (meth) acrylate compound (a2) include aliphatic hydroxyl mono (meth) acrylate compounds such as hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl acrylate and the like, aliphatic hydroxypoly (meth) acrylate compounds such as glycerol di (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate and the like, aromatic hydroxyl mono (meth) acrylate compounds such as 4-hydroxyphenyl acrylate, β -hydroxyphenyl acrylate, 4-hydroxyphenyl ethyl acrylate, 1-phenyl-2-hydroxyethyl acrylate, 3-hydroxy-4-acetylphenyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate and the like, polyoxyalkylene-modified (meth) acrylate compounds obtained by ring-opening polymerization of the above various hydroxyl (meth) acrylate compounds with various cyclic compounds such as ethylene oxide, propylene oxide, tetrahydrofuran, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, allyl glycidyl ether, glycidyl ether and the like, and 2 or more of these compounds may be used alone or in combination with one or more compounds such as the above-caprolactone lactone compound.
Among the hydroxyl (meth) acrylate compounds (a2), the aliphatic hydroxyl mono (meth) acrylate compounds, the aliphatic hydroxyl poly (meth) acrylate compounds, and polyoxyalkylene-modified products or lactone-modified products thereof are preferable, lactone-modified aliphatic hydroxyl (meth) acrylate compounds are more preferable, and lactone-modified aliphatic hydroxyl mono (meth) acrylate compounds are particularly preferable, because a printing ink having excellent fluidity and print surface gloss and having excellent general printing suitability such as ink misting resistance and emulsion suitability can be obtained. Further, the ratio of the lactone-modified aliphatic hydroxy mono (meth) acrylate compound in the hydroxy (meth) acrylate compound (a2) is preferably 70% by mass or more, and more preferably 90% by mass or more.
The acid group-containing hydroxyl compound (a3) may have an acid group such as a carboxyl group and a hydroxyl group in its molecular structure, and the number of carboxyl groups and hydroxyl groups and other specific structures are not particularly limited. The acid group-containing hydroxyl compounds (a3) may be used alone or in combination of 2 or more. Among these, aliphatic compounds are preferable from the viewpoint of obtaining a printing ink having more excellent fluidity and gloss on the printed surface, and compounds having 1 to 3 carboxyl groups and 1 to 3 hydroxyl groups on an aliphatic hydrocarbon having 2 to 20 carbon atoms are more preferable. Specific examples of such compounds include monohydroxy compounds such as glycolic acid, lactic acid, hydroxybutyric acid, hydroxypentanoic acid, hydroxycaproic acid, hydroxyheptanoic acid, hydroxyoctanoic acid, hydroxynonanoic acid, hydroxydecanoic acid, hydroxydodecanoic acid, hydroxytetradecanoic acid, hydroxyhexadecanoic acid, hydroxyheptadecanoic acid, hydroxyoctadecanoic acid (hydroxystearic acid), ricinoleic acid, and the like; dihydroxy compounds such as glyceric acid, 2- (hydroxymethyl) -3-hydroxypropionic acid, 2- (dihydroxymethyl) propionic acid, dimethylolpropionic acid, and 3, 3-dimethylolpropionic acid; trihydroxy compounds such as 3-hydroxy-2, 2-bis (hydroxymethyl) propionic acid, and the like.
The acid group-containing urethane (meth) acrylate resin (a) may be prepared by using the polyisocyanate compound (a1), the hydroxyl (meth) acrylate compound (a2), and the acid group-containing hydroxyl compound (a3) in combination, and may be prepared by using other reaction raw materials in combination. Examples of the other reaction raw materials include polyol compounds other than the hydroxyl (meth) acrylate compound (a2) and the acid group-containing hydroxyl compound (a 3). Examples of the polyol compound include: aliphatic polyhydric alcohol compounds such as ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, glycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol and the like; aromatic polyhydric alcohol compounds such as biphenol and bisphenol; (poly) oxyalkylene modified products obtained by introducing a (poly) oxyalkylene chain such as a (poly) oxyethylene chain, a (poly) oxypropylene chain, or a (poly) oxytetramethylene chain into the molecular structure of the above-mentioned various polyol compounds; lactone modifications obtained by introducing a (poly) lactone structure into the molecular structure of the above-mentioned various polyol compounds, and the like.
In the case where the other reaction raw materials are used, the ratio of the total mass of the polyisocyanate compound (a1), the hydroxyl (meth) acrylate compound (a2) and the acid group-containing hydroxyl compound (a3) to the reaction raw materials of the acid group-containing urethane (meth) acrylate resin (a) is preferably 70 mass% or more, more preferably 90 mass% or more, from the viewpoint of sufficiently exhibiting the effects of the present invention.
The method for producing the urethane (meth) acrylate resin (a) having an acid group is not particularly limited, and the urethane (meth) acrylate resin (a) can be produced by a method similar to that for a general urethane (meth) acrylate resin. The reaction ratio, reaction order, and the like of the components may be appropriately adjusted according to the desired resin design and resin performance, and are not particularly limited. Examples of the reaction conditions include the following methods: the reaction raw materials are used in such a proportion that the hydroxyl group in the reaction raw materials is in the range of 0.9 to 1.1 mol per 1 mol of isocyanate group in the reaction raw materials, and are heated at 20 to 120 ℃. In this reaction, a known and conventional urethanization catalyst such as zinc octoate, various antioxidants, a polymerization inhibitor, and the like may be used as desired.
The acid value of the acid group-containing urethane (meth) acrylate resin (A) is preferably in the range of 1 to 50mgKOH/g, more preferably in the range of 3 to 40mgKOH/g, and particularly preferably in the range of 3 to 35mgKOH/g, from the viewpoint that a printing ink having more excellent fluidity and gloss of a printed surface can be obtained. In the present invention, the acid value of the resin is a value measured by neutralization titration method of JIS K0070 (1992).
The mass average molecular weight (Mw) of the acid group-containing urethane (meth) acrylate resin (a) is preferably in the range of 1,000 to 25,000, more preferably in the range of 1,000 to 10,000, from the viewpoint that a printing ink having more excellent fluidity and gloss on a printing surface can be obtained when used for a printing ink.
In the present invention, the molecular weight of the resin is a value measured by Gel Permeation Chromatography (GPC) under the following conditions.
A measuring device; HLC-8220GPC, manufactured by Tosoh corporation
A column; TSK-GUARDCOLUMN SuperHZ-L manufactured by Tosoh corporation
+ Tosoh corporation TSK-GEL SuperHZM-Mx 4
A detector; RI (differential refractometer)
Processing data; multi station GPC-8020model II, manufactured by Tosoh corporation
Measuring conditions; column temperature 40 deg.C
Solvent tetrahydrofuran
Flow rate 0.35 ml/min
Standard; monodisperse polystyrene
A sample; the resulting tetrahydrofuran solution (0.2 mass% in terms of resin solid content) was filtered through a microfilter (100. mu.l)
Examples of the metal complex (B) include: aluminum trialkoxides such as aluminum triethoxide, aluminum tripropoxide, aluminum dipropionate monobutyrate, aluminum tributanolate, etc.; aluminum alkyl acetoacetates such as aluminum dipropyl acetoacetate, aluminum dibutyl acetoacetate, aluminum triacetoacetate, aluminum dipropyl ethylacetoacetate, aluminum tri (ethylacetoacetoxy) and aluminum dipropyl octadecylacetoacetate; titanium tetraalkoxides such as titanium tetraalkoxide and titanium tetrabutoxide; titanium alkyl acetoacetates such as bis (acetoacetoxy) titanium dipropyl ester; zirconium tetraalkoxide such as zirconium tetrabutoxide, and the like. Specific examples of commercially available products include Aluminum organic compound series ("AMD", "ASBD", "AIPD", "PADM", "Aluminum ethoxide", "ALCH-TR", "Aluminum Chemical complex M", "Aluminum Chemical complex D", "Aluminum Chemical complex A, A (W)"), Ajinomoto Fine-Techno Co., and "pleact" series ("AL-M", "TTS"), Matsumotofine Chemical Co. Lt. GARTTIX "series (" AL-3001 "," AL-3100 "," AL-3200 "," AL-8 "," TA-21 "," TA-23 "," TA-30 "," TC-401 "," TC-710-TC-750 "," ZA-65 "," ZA-3213213215 ", and" TD "series, "AC-150", "ZC-540"), etc. The metal complex (B) may be used singly or in combination of two or more.
The amount of the metal complex (B) to be blended may be appropriately adjusted depending on the desired ink performance, and is preferably in the range of 0.5 to 20 parts by mass, and more preferably in the range of 1 to 15 parts by mass, based on 100 parts by mass of the acid group-containing urethane (meth) acrylate resin (a), in particular, from the viewpoint of forming a printing ink having high fluidity, excellent gloss of a printed surface, and sufficiently high resistance to ink misting, emulsification suitability, and other properties.
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). Examples of the other resin component (C) include various (meth) acrylate monomers (C1), urethane (meth) acrylate resins other than the component (a) (C2), epoxy (meth) acrylate resins (C3), polyester (meth) acrylate resins (C4), ketone resins (C5), diallyl phthalate (DAP) resins (C6), and the like. The effect of the present invention, that is, the effect of forming a printing ink having high fluidity and excellent gloss of a printed surface by using a composition containing an acid group-containing urethane (meth) acrylate resin (a) and a metal complex (B) for a printing ink, can be sufficiently exhibited regardless of the resin of the other resin component (C). Therefore, the other resin component (C) may be any of various resin materials that can be used for printing ink, and is not particularly limited.
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; alicyclic mono (meth) acrylate compounds such as cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and adamantyl mono (meth) acrylate; heterocyclic mono (meth) acrylate compounds such as glycidyl (meth) acrylate and tetrahydrofurfuryl acrylate; aromatic mono (meth) acrylate compounds such as benzyl (meth) acrylate and phenoxy (meth) acrylate; hydroxyl group-containing mono (meth) acrylate compounds such as hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate; polyoxyalkylene-modified mono (meth) acrylate compounds obtained by introducing a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain, or a polyoxytetramethylene chain into the molecular structure of each of the above mono (meth) acrylate compounds; lactone-modified mono (meth) acrylate compounds obtained by introducing a (poly) lactone structure into the molecular structure of each of the above-mentioned mono (meth) acrylate compounds;
aliphatic di (meth) acrylate compounds such as ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butylene glycol 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 and tricyclodecanedimethanol di (meth) acrylate; aromatic di (meth) acrylate compounds such as biphenol di (meth) acrylate and bisphenol di (meth) acrylate; polyoxyalkylene-modified di (meth) acrylate compounds obtained by introducing a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain, or a polyoxytetramethylene chain into the molecular structure of each of the above di (meth) acrylate compounds; lactone-modified di (meth) acrylate compounds obtained by introducing a (poly) lactone structure into the molecular structure of each of the above di (meth) acrylate compounds;
aliphatic tri (meth) acrylate compounds such as trimethylolpropane tri (meth) acrylate and glycerol tri (meth) acrylate; hydroxyl group-containing tri (meth) acrylate compounds such as pentaerythritol tri (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, and dipentaerythritol tri (meth) acrylate; polyoxyalkylene-modified tri (meth) acrylate compounds obtained by introducing a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain, or a polyoxytetramethylene chain into the molecular structure of each of the above tri (meth) acrylate compounds; lactone-modified tri (meth) acrylate compounds obtained by introducing a (poly) lactone structure into the molecular structure of each of the above tri (meth) acrylate compounds;
aliphatic poly (meth) acrylate compounds having 4 or more functions such as pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, and dipentaerythritol hexa (meth) acrylate; 4 or more functional hydroxyl group-containing poly (meth) acrylate compounds such as dipentaerythritol tetra (meth) acrylate and dipentaerythritol penta (meth) acrylate; polyoxyalkylene-modified poly (meth) acrylate compounds having 4 or more functions, which are obtained by introducing a polyoxyalkylene chain such as a polyoxyethylene chain, a polyoxypropylene chain or a polyoxytetramethylene chain into the molecular structure of each of the above poly (meth) acrylate compounds; lactone-modified poly (meth) acrylate compounds having 4 or more functions, which are obtained by introducing a (poly) lactone structure into the molecular structure of each of the above-mentioned poly (meth) acrylate compounds.
Examples of the urethane (meth) acrylate resin (C2) include: various polyisocyanate compounds, hydroxyl group-containing (meth) acrylate compounds, and, if necessary, various polyol compounds. Specific examples of these reaction raw materials include those exemplified in the description of the urethane (meth) acrylate resin (a) having an acid group.
Examples of the epoxy (meth) acrylate compound (C3) include (meth) acrylates of epoxy group-containing compounds such as bisphenol epoxy resins and 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 any (meth) acrylate resin having a polyester structural site in its molecular structure, and may be an alkyd resin type in which a part of the reaction raw materials contains an oil or fat or a fatty acid, or a urethane-modified type in which a part of the reaction raw materials contains a polyisocyanate.
In the composition of the present invention, the amount of the other resin component (C) to be blended may be appropriately adjusted depending on the desired ink performance and the like, and from the viewpoint of more effectively exhibiting the effect of the present invention, the total mass of the acid group-containing urethane (meth) acrylate resin (a) and the metal complex (B) is preferably in the range of 0.5 to 20 mass%, and more preferably in the range of 1 to 10 mass% with respect to the total mass of the acid group-containing urethane (meth) acrylate resin (a), the metal complex (B) and the other resin component (C).
The composition of the present invention can be suitably used mainly for an active energy ray-curable printing ink, and preferably contains a photopolymerization initiator corresponding to an active energy ray to be irradiated. Examples of the photopolymerization initiator include alkylphenone-based photopolymerization initiators such as 1-hydroxy-cyclohexyl-phenyl-ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, and 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [4- (4-morpholino) phenyl ] -1-butanone; acylphosphine oxide-based photopolymerization initiators such as 2,4, 6-trimethylbenzoyl-diphenyl-phosphine oxide; and intramolecular hydrogen abstraction type photopolymerization initiators such as benzophenone compounds. These may be used alone or in combination of 2 or more. The photopolymerization initiator may be selected appropriately according to the type of the active energy ray to be irradiated.
Examples of commercially available products of the photopolymerization initiator include "IRGACURE" series ("IRGACURE 127", "IRGACURE 184", "IRGACURE 250", "IRGAC URE 270", "IRGACURE 290", "IRGACURE 369E", "IRGACURE 379 EG", "IRGACURE 500", "IRGACURE 651", "IRGACURE 754", "IRGACURE 819", "IRGACURE 907", "IRGACURE 1173", "IRGACURE 2959", "IRGACURE MBF", "IRGACURE TPO", "IRGACURE OXE 01", "IRGACURE OXE 02", "IRGACURE 907", "IRGACURE 1173", "OMNIRAD" series ("OMNIRAD 184", "OMNIRADA 250", "OMNIRADARD 369E", "OMNI 651", "OMNI 907", "PHNI ZO DYNACURE 550", and "OME HOMOCURE SUGACURE 550", manufactured by BASF corporation. These photopolymerization initiators are preferably used in an amount of about 0.05 to 20 parts by mass based on 100 parts by mass of the total composition.
The composition of the present invention may contain a photosensitizer together with the aforementioned polymerization initiator. Examples of the photosensitizer include amine compounds such as aliphatic amines, ureas such as o-tolylthiourea, sulfur compounds such as sodium diethyldithiophosphate and S-benzylisothiouronium p-toluenesulfonate. These photosensitizers are preferably used in an amount of about 0.1 to 10 parts by mass based on 100 parts by mass of the total composition.
The composition of the present invention may further contain various additives contained in a usual printing ink, such as a pigment, a dye, an extender pigment, an organic or inorganic filler, an organic solvent, an antistatic agent, an antifoaming agent, a viscosity modifier, a polymerization inhibitor, a light-resistant stabilizer, a weather-resistant stabilizer, a heat-resistant stabilizer, an ultraviolet absorber, an antioxidant, a leveling agent, a pigment dispersant, and wax.
Examples of the pigment include known and publicly known organic pigments for coloring, and examples thereof include organic pigments for printing inks described in "organic pigment handbook (author: color office, first edition 2006)", and soluble azo pigments, insoluble azo pigments, condensed azo pigments, metal phthalocyanine pigments, metal-free phthalocyanine pigments, quinacridone pigments, perylene pigments, pyrene pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, thioindigo pigments, anthraquinone pigments, quinophthalone pigments, metal complex pigments, diketopyrrolopyrrole pigments, carbon black pigments, and other polycyclic pigments. The amount of these pigments to be added is preferably 5 to 30 parts by mass based on 100 parts by mass of the total composition, although the optimum amount varies depending on the type of pigment and the like.
Examples of the extender pigment include titanium oxide, graphite, 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, and glass beads. The amount of these extender pigments is preferably 0.1 to 20 parts by mass based on 100 parts by mass of the total composition, although the optimum amount varies depending on the type of pigment and the like.
In the composition and the printing ink of the present invention, the blending ratio of each component and the like is not particularly limited, and the blending ratio can be appropriately adjusted according to the intended printing application, performance and the like. All the components may be mixed at once, or a part of the components may be mixed to prepare a premixed composition and then mixed with the other components in a batch manner. 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 using a three-roll mill, and a method using a disperser such as a bead mill.
The printing ink of the present invention can be cured by irradiation with active energy rays, for example, ionizing radiation rays such as ultraviolet rays, electron rays, α rays, β rays and γ rays.
The printing ink of the present invention can be used for printing on various substrates such as paper and various plastic films. Specifically, the following base materials can be used as the printing object: paper substrates used for catalogs, posters, flyers, CD cases, direct mail advertisements, brochures, packages for cosmetics or beverages, pharmaceuticals, toys, machines, and the like; plastic film substrates for packaging materials such as polypropylene films and polyethylene terephthalate films, for food, beverage and cosmetics; aluminum foil, synthetic paper, and various other substrates that have been used as printing substrates.
The printing method of the printing ink of the present invention is not particularly limited, and printing can be performed by offset lithography, relief printing, gravure offset printing, flexo printing, screen printing, or the like, for example. Among them, the present invention is particularly suitable for offset printing in which water is continuously supplied to a plate surface. The offset printing press for continuously supplying water is manufactured and sold by a plurality of printing press manufacturers, and examples thereof include Heidelberg Corporation, KOMORI Corporation, RYOBI MHI graphics technology ltd., manroland AG, KBA Corporation, and the like, and the present invention can be suitably used in a sheet-fed offset printing press using sheet-form printing paper, an offset rotary printing press using roll-form printing paper, and any paper supply system. More specifically, there are offset printing machines such as Speedmaster series manufactured by Heidelberg corporation, RISURON series manufactured by komorico corporation, and Diamond series manufactured by RYOBI MHI Graphic Technology ltd.
Examples
The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.
Determination of Infrared absorption Spectroscopy
[ model ] FT/IR-4100 manufactured by Nippon spectral Co., Ltd
[ measurement conditions]By confirming 2250cm representing isocyanate group-1The completion of the reaction was confirmed by the infrared absorption spectrum of (2).
Determination of Mass average molecular weight (Mw)
The measurement was performed by Gel Permeation Chromatography (GPC) under the following conditions.
A measuring device; HLC-8220GPC, manufactured by Tosoh corporation
A column; TSK-GUARDCOLUMN SuperHZ-L manufactured by Tosoh corporation
+ Tosoh corporation TSK-GEL SuperHZM-Mx 4
A detector; RI (differential refractometer)
Processing data; multi station GPC-8020model II, manufactured by Tosoh corporation
Measuring conditions; column temperature 40 deg.C
Solvent tetrahydrofuran
Flow rate 0.35 ml/min
Standard; monodisperse polystyrene
A sample; a tetrahydrofuran solution (0.2 mass% in terms of solid content of resin) was filtered through a microfilter (100. mu.l)
Acid value measurement conditions
The measurement was carried out by a neutralization titration method according to JIS K0070 (1992).
Production example 1 production of urethane (meth) acrylate resin (A-1)
187.1 parts by mass of lactone-modified hydroxyethyl acrylate ("PLACCEL FA 2D" manufactured by Daicel Corporation), 16.1 parts by mass of 12-hydroxystearic acid, and 0.17 part by mass of N-nitroso-N-phenylhydroxylamine aluminum were charged in a flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, and the flask was heated to 65 ℃. 108.6 parts by mass of isocyanurate-modified hexamethylene diisocyanate (Sumika Covestro Urethane Co., Ltd., "Sumidur N3300" by Ltd.) was added dropwise over 1 hour. After the end of the dropwise addition, the mixture was heated to 95 ℃ and reacted for 2 hours. 2250cm showing an isocyanate group was confirmed-1The infrared absorption spectrum of (A) was lost, and the target urethane (meth) acrylate resin (A-1) was obtained. The urethane (meth) acrylate resin (A-1) had a mass average molecular weight (Mw) of 4,477 and an acid value of 11.2 mgKOH/g.
Production example 2 production of urethane (meth) acrylate resin (A-2)
143.3 parts by mass of lactone-modified hydroxyethyl acrylate ("PLACCEL FA 2D" manufactured by Daicel Corporation), 6.0 parts by mass of 12-hydroxystearic acid, and 0.12 part by mass of N-nitroso-N-phenylhydroxylamine aluminum were charged into a flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, and the flask was heated to 65 ℃. 79.8 parts by mass of isocyanurate-modified hexamethylene diisocyanate (Sumika Covestro Urethane Co., Ltd., "Sumidur N3300" by Ltd.) was added dropwise over 1 hour. After the end of the dropwise addition, the mixture was heated to 95 ℃ and reacted for 2 hours. 2250cm showing an isocyanate group was confirmed-1The infrared absorption spectrum of (A) was lost, and the target urethane (meth) acrylate resin (A-2) was obtained. The urethane (meth) acrylate resin (A-2) had a mass average molecular weight (Mw) of 4,275 and an acid value of 6.0 mgKOH/g.
Production example 3 production of urethane (meth) acrylate resin (A-3)
116.4 parts by mass of lactone-modified hydroxyethyl acrylate ("PLACCEL FA 2D" manufactured by Daicel Corporation), 31.3 parts by mass of 12-hydroxystearic acid, and 0.12 part by mass of N-nitroso-N-phenylhydroxylamine aluminum were charged into a flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, and the flask was heated to 65 ℃. The isocyanurate is added dropwise in 1 hour79.1 parts by mass of hexamethylene diisocyanate ("Sumidur N3300" manufactured by Ltd.). After the end of the dropwise addition, the mixture was heated to 95 ℃ and reacted for 2 hours. 2250cm showing an isocyanate group was confirmed-1The infrared absorption spectrum of (A) was lost, and the target urethane (meth) acrylate resin (A-3) was obtained. The urethane (meth) acrylate resin (A-3) had a mass average molecular weight (Mw) of 4,663 and an acid value of 27.3 mgKOH/g.
Production example 4 production of urethane (meth) acrylate resin (A-4)
A flask equipped with a stirrer, a gas inlet tube, a condenser and a thermometer was charged with 201.4 parts by mass of lactone-modified hydroxyethyl acrylate ("PLACCEL FA 2D" manufactured by Daicel Corporation), 3.8 parts by mass of glycolic acid, and 0.17 part by mass of N-nitroso-N-phenylhydroxylamine aluminum, and heated to 65 ℃. 116.7 parts by mass of isocyanurate-modified hexamethylene diisocyanate (Sumika Covestro Urethane Co., Ltd., "Sumidur N3300" by Ltd.) was added dropwise over 1 hour. After the end of the dropwise addition, the mixture was heated to 95 ℃ and reacted for 2 hours. 2250cm showing an isocyanate group was confirmed-1The infrared absorption spectrum of (A) was lost, and the target urethane (meth) acrylate resin (A-4) was obtained. The urethane (meth) acrylate resin (A-4) had a mass average molecular weight (Mw) of 4,135 and an acid value of 8.9 mgKOH/g.
Production example 5 production of urethane (meth) acrylate resin (A-5)
167.9 parts by mass of lactone-modified hydroxyethyl acrylate ("PLACCEL FA 2D" manufactured by Daicel Corporation), 3.4 parts by mass of dimethylolpropionic acid, and 0.17 part by mass of N-nitroso-N-phenylhydroxylamine aluminum were charged in a flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer, and the flask was heated to 65 ℃. 116.9 parts by mass of isocyanurate-modified hexamethylene diisocyanate ("Sumidur N3300" by Ltd.) was added dropwise over 1 hour. After the end of the dropwise addition, the mixture was heated to 95 ℃ and reacted for 2 hours. 2250cm showing an isocyanate group was confirmed-1The infrared absorption spectrum of (A) was lost, and the target urethane (meth) acrylate resin (A-5) was obtained. The urethane (meth) acrylate resin (A-5) had a mass average molecular weight (Mw) of 4,389 and an acid valueIs 5.5 mgKOH/g.
Examples 1 to 7 production of compositions (1) to (8)
The respective components were blended at the ratios shown in table 1 below, and stirred for 1 hour to obtain compositions (1) to (8). Details of the metal complex are as follows.
(meth) acrylate monomer: "OTA 480" manufactured by DAICEL-ALLNEX LTD, propylene oxide-modified glycerol triacrylate, and an average addition number of 3 per 1 molecule of propylene oxide
Metal complex (B-1): "ALCH-TR" manufactured by Kawaken Fine Chemicals Co., Ltd., tris (ethylacetoacetato) aluminum
Metal complex (B-2): ajinomoto Fine-Technio Co., Inc. "plenactAL-M" manufactured by Inc., and diisopropyl alkyl aluminum acetoacetate
[ Table 1]
Production of printing inks of examples 9 to 21 and comparative example 1
The components were blended at the ratios shown in tables 3 to 5 below, stirred by a mixer (uniaxial dissolver), and then ground by a three-roll mill to obtain printing inks. In example 14, components other than the composition (1) were blended, stirred by a mixer (uniaxial dissolver), ground by a three-roll mill, and then the composition (1) was added and mixed to obtain a printing ink.
The obtained printing ink was evaluated in the following manner. The results are shown in tables 3 to 5.
[ Table 2]
Production example 6 production of urethane (meth) acrylate resin
60.3 parts by mass of polymeric diphenylmethane diisocyanate ("Millionate MR-400" manufactured by Nippon polyurethane industries, Ltd.), 0.1 part by mass of t-butylhydroxytoluene, and a solvent were placed in a four-necked flask equipped with a stirrer, a gas inlet tube, a condenser, and a thermometer,0.02 part by mass of methoxyl hydroquinone and 0.02 part by mass of zinc octoate, and heating to 75 ℃. 35.7 parts by mass of 2-hydroxyethyl acrylate was added dropwise thereto over 1 hour while stirring the flask. After completion of the dropwise addition, the reaction was further carried out at 75 ℃ for 3 hours. 4.0 parts by mass of glycerin was added, and the reaction was continued at 75 ℃ to confirm 2250cm of isocyanate group-1The infrared absorption spectrum of (2) disappears, and a urethane (meth) acrylate resin is obtained.
Evaluation of fluidity
In a room air-conditioned to 25 ℃, 1.0ml of printing ink was placed at the upper end of a glass plate at an angle of 70 ° to the ground plane, and the distance of flow was determined after 1 day. The larger the value, the better the fluidity.
Method for making color-spreading object
0.10ml of printing ink was uniformly stretched over a rubber roll and a metal roll of a RItester using a simple developing machine ("RI tester" manufactured by Fengron Seiki Seisaku-Sho Ltd.). Color development was performed so that the surface of the art paper (Ok gold rattan single side manufactured by Wangzi paper Co., Ltd.) covered by 200cm2The area (A) was uniformly coated with a yellow concentration of 1.4 (measured by a SpectroEye densitometer, manufactured by X-Rite Co., Ltd.) to prepare a color-developed product. The RI tester is a tester for developing ink on paper or film, and can adjust the amount of ink transferred and the printing pressure.
Curing method using Ultraviolet (UV) lamp light source
The developed color material obtained above is irradiated with Ultraviolet (UV) rays to cure the printing ink. Specifically, a spread was placed on a belt conveyor using an Ultraviolet (UV) irradiation device (EYE graphic sco., ltd., with a cold mirror) equipped with a water-cooled metal halide lamp (120W/cm 1 lamp) and the belt conveyor, and the printing ink was cured by passing the spread directly under the lamp (irradiation distance 11cm) at a speed of 40 m.
Gloss of printed surface
The gloss value of the printed surface of the cured color developed material was measured with a 60 ℃ gloss meter (manufactured by BYK Garder GmbH) and evaluated on the following 3 grades. Higher values indicate better gloss.
(evaluation criteria)
A: gloss above 55%
B: gloss 45 or more and less than 55
C: gloss less than 45
[ Table 3]
[ Table 4]
[ Table 5]
Claims (9)
1. A composition comprising: an acid group-containing urethane (meth) acrylate resin (A), and a metal complex (B).
2. The composition according to claim 1, wherein the acid value of the acid group-containing urethane (meth) acrylate resin (a) is in the range of 1 to 50 mgKOH/g.
3. The composition according to claim 1, wherein the mass average molecular weight (Mw) of the acid group-containing urethane (meth) acrylate resin (A) is in the range of 1,000 to 25,000.
4. The composition according to claim 1, wherein the urethane (meth) acrylate resin (A) having an acid group comprises a polyisocyanate compound (a1), a hydroxyl (meth) acrylate compound (a2) and an acid group-containing hydroxyl compound (a3) as essential reaction raw materials.
5. The composition according to claim 1, wherein the central metal of the metal complex (B) is any of aluminum, titanium, and zirconium.
6. The composition according to claim 1, wherein the amount of the metal complex (B) is in the range of 0.5 to 20 parts by mass per 100 parts by mass of the acid group-containing urethane (meth) acrylate resin (A).
7. The composition according to claim 1, wherein the composition further contains a resin component (C) in addition to the acid group-containing urethane (meth) acrylate resin (A) and the metal complex (B), and the total mass of the acid group-containing urethane (meth) acrylate resin (A) and the metal complex (B) is in the range of 0.5 to 20 mass% relative to the total mass of the resin component (C).
8. A printing ink comprising the composition according to any one of claims 1 to 7.
9. A printed article obtained by printing the printing ink according to claim 8.
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| JP2017-141811 | 2017-07-21 | ||
| JP2017141811 | 2017-07-21 | ||
| PCT/JP2018/026290 WO2019017270A1 (en) | 2017-07-21 | 2018-07-12 | Composition and printing ink |
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| JP7464455B2 (en) | 2020-06-18 | 2024-04-09 | Ｄｉｃグラフィックス株式会社 | Active energy ray curable ink for lithographic offset printing, its manufacturing method, manufacturing method of cured ink, and printed matter |
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