CN111801393B - Active energy ray-curable ink, method for producing cured ink, and printed matter - Google Patents
Active energy ray-curable ink, method for producing cured ink, and printed matter Download PDFInfo
- Publication number
- CN111801393B CN111801393B CN201980017173.5A CN201980017173A CN111801393B CN 111801393 B CN111801393 B CN 111801393B CN 201980017173 A CN201980017173 A CN 201980017173A CN 111801393 B CN111801393 B CN 111801393B
- Authority
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- China
- Prior art keywords
- ink
- active energy
- energy ray
- meth
- acrylate
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 238000007639 printing Methods 0.000 claims abstract description 44
- 239000003999 initiator Substances 0.000 claims abstract description 34
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- SGLSVXFFMZXOBG-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-piperidin-1-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCCCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 SGLSVXFFMZXOBG-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 tertiary amine compound Chemical class 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
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- 238000007645 offset printing Methods 0.000 claims description 7
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- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 abstract description 5
- 239000000976 ink Substances 0.000 description 88
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 68
- 239000000049 pigment Substances 0.000 description 27
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- 239000000123 paper Substances 0.000 description 14
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- 238000001723 curing Methods 0.000 description 7
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 6
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- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 5
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 2
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 2
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
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- 108090000623 proteins and genes Proteins 0.000 description 1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 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
- 150000003573 thiols Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 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
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
Abstract
The present application relates to: an active energy ray-curable ink containing a monomer having an ethylenically unsaturated double bond and a photopolymerization initiator represented by the general formula (1); a method for producing a cured ink material by printing with the active energy ray-curable ink and curing the printed ink with an active energy ray; and a printed matter. The photopolymerization initiator represented by the general formula (1) is preferably 2-benzyl-2-dimethylamino-1- (4-piperidinophenyl) -butan-1-one. (wherein n represents 0 or 1, R) 1 ～R 4 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms).
Description
Technical Field
The present invention relates to an active energy ray-curable ink, a method for producing a cured product of the active energy ray-curable ink, and a printed matter.
Background
The active energy ray-curable ink is a solvent-free type and can be cured and dried by active energy rays instantaneously, and therefore is considered to be capable of obtaining a high-quality print excellent in environmental friendliness and printing workability, and is used as an ink in various printing systems such as lithographic printing (general lithographic printing using dampening water and non-dampening lithographic printing using no dampening water), relief printing, gravure printing, stencil printing, offset printing, and the like, and applied to various prints such as a print for foam, various book prints, various packaging prints such as cardboard, various plastic prints, stickers, a print for labels, art prints, metal prints (food prints such as art prints, beverage can prints, cans, and the like), and the like.
As a light source of these active energy ray-curable inks, ultraviolet lamps (UV lamps) such as low-pressure or high-pressure mercury lamps, xenon lamps, and metal halide lamps have been widely used, but in recent years, irradiation modules using ultraviolet light emitting diodes (UV-LEDs) as light sources have been developed and are gradually applied to the field of UV printing.
An ultraviolet light emitting diode (UV-LED) generates ultraviolet rays having an emission peak wavelength in the range of 350 to 420 nm. That is, in order to apply an ink originally using a light source such as a conventional metal halogen lamp or a high-pressure mercury lamp to a UV-LED, it is necessary to use a photopolymerization initiator having absorption at a wavelength of about 350 to 420nm, but since a pigment used in the ink itself absorbs light in a wavelength range of 350 to 420nm, there is a problem that curing is insufficient even if a photopolymerization initiator having absorption at a wavelength of 350 to 420nm is used in most cases.
As ink compositions for UV-LED applications, for example: an active energy ray-curable ink using an α - (dimethyl) aminoalkylbenzophenone compound and/or an α -morpholinoalkylphenone compound, and a dialkylaminobenzophenone compound (A2-1) and/or a thioxanthone compound in combination as a photopolymerization initiator (see, for example, patent document 1); an active energy ray-curable ink which uses an α -aminoalkylphenone compound and an acylphosphine oxide compound together as a photopolymerization initiator and contains a specific alcohol (see, for example, patent document 2). However, the ultraviolet absorption region of the α -aminoalkylphenone compound is located on the shorter wavelength side, and when it is cured by a UV-LED, the curability of the coating film surface may be poor. In addition, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one (Irgacure 907), which is commonly used as an α -morpholinoalkylphenone compound, generates a specific odor immediately after irradiation with ultraviolet light, and therefore, the amount of the compound to be added is limited in applications requiring high hygiene, and sufficient curability cannot be obtained.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 2015-193677
Patent document 2: japanese patent laid-open publication No. 2011-236277
Disclosure of Invention
Problems to be solved by the invention
The present inventors provide an active energy ray-curable ink which cures very quickly even when a UV-LED light source is used and which is less likely to generate odor or the like.
Means for solving the problems
The present inventors have found that the above problems can be solved by an active energy ray-curable ink containing a specific photopolymerization initiator.
That is, the present invention provides an active energy ray-curable ink containing a monomer having an ethylenically unsaturated double bond and a photopolymerization initiator represented by the general formula (1):
[ chemical formula 1]
(wherein n represents 0 or 1 1 ～R 4 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms).
The present invention also provides a method for producing a cured ink, which comprises printing with the active energy ray-curable ink described above and curing the printed ink with an active energy ray.
The present invention also provides a method for producing a cured ink, which comprises performing offset printing using the active energy ray-curable ink described above, and curing the printed ink using an active energy ray.
The present invention also provides a printed matter obtained by the method for producing a cured ink material described above.
Effects of the invention
According to the present invention, since an active energy ray-curable ink which cures very quickly even when a UV-LED light source is used as an ultraviolet light source and is less likely to generate odor or the like can be obtained, the ink can be used without any problem in the field of package printing which requires hygiene.
The ink of the present invention can be used as inks for various conventionally known printing methods, such as offset printing inks, letterpress printing inks, intaglio printing inks, and stencil printing inks.
Detailed Description
(photopolymerization initiator represented by the general formula (1))
In the photopolymerization initiator represented by the general formula (1) used in the present invention, n represents 0 or 1 1 ～R 4 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms.
[ chemical formula 2]
As the above-mentioned R 1 ～R 4 Examples of the straight-chain or branched alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a pentyl group, an isopentyl group, a hexyl group, a heptyl group, an isoheptyl group, an octyl group, an isooctyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, and a decyl group.
In the above general formula (1), R 1 ～R 4 Each independently is preferably a linear or branched alkyl group having 1 to 5 carbon atoms, and n is more preferably 0. Examples of the photopolymerization initiator of the present invention include 2-benzyl-2-dimethylamino-1- (4-piperidinophenyl) -butan-1-one (also known as 2-benzyl-2-dimethylamino-1- (4-piperidinophenyl) -butanone-1, 2-benzyl-2-dimethylamino-1- (4-piperidinophenyl) -1-butanone, etc.) shown below.
In the present invention, the content of the photopolymerization initiator represented by the above general formula (1) is preferably 0.5 to 10% by mass, more preferably 1.0 to 5.0% by mass, based on the total amount of the solid components of the ink. When the amount is 0.5% by mass or less, the active free genes generated by ultraviolet irradiation are inactivated by oxygen in the air, and the curability of the ink is remarkably reduced. Therefore, if the odor of the unreacted material from the ink raw material is increased or the surface of the printed matter is scratched to cause a poor appearance and the surface of the printed matter is stacked on the back surface of the printed matter discharged onto the printed matter, a problem called blocking occurs in which the surface of the printed matter is in close contact with the back surface of the printed matter on top of the surface of the printed matter. On the other hand, when the amount is 10% by mass or more, the photopolymerization initiator is likely to precipitate, and the initiator precipitates in the ink within several days immediately after the production of the ink, so that the designed curing performance of the ink cannot be exhibited. Further, particles of the initiator precipitated in the ink may accumulate on a roller or a plate of the printer, and an accurate image may not be formed.
[ combination of general photopolymerization initiators ]
In the present invention, in addition to the photopolymerization initiator represented by the above general formula (1), a general photopolymerization initiator may be appropriately used in combination, as long as the effects of the present invention are not impaired, in view of the type of the ultraviolet light source used, the irradiation intensity of the ultraviolet light source, the cumulative amount of ultraviolet light irradiation, the color, the thickness of the printed film, the hygienic property, and the like. Examples include 2, 2-dimethoxy-1, 2-diphenylethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one, methyl phenylglyoxylate, hydroxyphenylacetic acid, a mixture of 2- [ 2-oxo-2-phenylacetyloxyethoxy ] ethyl ester and hydroxyphenylacetic acid, 2- (2-hydroxyethoxy) ethyl ester, 1, 2-octanedione, 1- [4- (phenylthio) -,2- (o-benzoyloxime) ], ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (o-acetyl oxime), 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, and mixtures thereof, 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [4- (4-morpholino) phenyl ] -1-butanone and the like.
Further, acylphosphine oxide compounds such as bis (2, 4, 6-trimethylbenzoyl) -phenylphosphine oxide, 2,4, 6-trimethylbenzoyl diphenylphosphine oxide and bis (2, 6-dimethoxybenzoyl) -2, 4-trimethyl-pentylphosphine oxide can be mentioned.
Further, thioxanthone compounds such as 2, 4-diethylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2, 4-dichlorothioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, and 2-hydroxy-3- (3, 4-dimethyl-9-oxo-9H-thioxanthone-2-yloxy-N, N, N-trimethyl-1-propylamine hydrochloride are exemplified.
Further, benzophenone compounds such as 4,4 '-dialkylaminobenzophenones, e.g., 4' -bis- (dimethylamino) benzophenone and 4,4 '-bis- (diethylamino) benzophenone, and 4-benzoyl-4' -methyldiphenylsulfide can be mentioned.
In addition, for example, benzophenone, 4-methyl-benzophenone, 2,4, 6-trimethyl benzophenone, 2,3, 4-trimethyl benzophenone, 4-phenyl benzophenone, 3' -dimethyl-4-methoxybenzophenone, 4- (1, 3-acryloyl-1, 4,7, 10, 13-pentadecyl) benzophenone, methyl-benzoylbenzoate, [4- (methylphenylsulfanyl) phenyl ] benzophenone, diethoxyacetophenone, dibutoxyacetophenone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin n butyl ether and the like can be given.
In the present invention, 1 or more than one type of the general-purpose photopolymerization initiator used in combination with the photopolymerization initiator represented by the general formula (1) can be used. Among these, the photopolymerization initiator represented by the above general formula (1) is preferably used in combination with the acylphosphine oxide compound, and particularly, from the viewpoint of solubility in a resin, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide is more preferably used in combination. When used in combination, the 2,4, 6-trimethylbenzoyldiphenylphosphine oxide is preferably contained in an amount of 70 to 2000% by mass, more preferably 70 to 1000% by mass, based on the photopolymerization initiator represented by the general formula (1). Further, the amount of 2,4, 6-trimethylbenzoyldiphenylphosphine oxide used when used in combination is preferably 1.0 to 15% by mass, more preferably 3.0 to 10% by mass, based on the total amount of the solid components of the ink. When the amount is less than 1.0% by mass, a sufficient effect of improving the curability cannot be obtained; if the amount exceeds 15% by mass, unreacted acylphosphine oxide remains in the cured coating film even after UV irradiation, and the cured coating film is discolored to a yellow color to such an extent that the hue of the cured coating film is not acceptable, or an initiator is precipitated, or the fluidity of the ink is significantly deteriorated.
[ sensitizer & photoinitiation assistant ]
The photosensitizer is a compound that absorbs ultraviolet light, transitions to an electron excited singlet state, transitions to a triplet state by intersystem crossing, and then undergoes energy transfer upon collision with a photopolymerization initiator in a ground state, thereby causing the photopolymerization initiator to transition to an excited triplet state. For example, when a light source having a narrow emission wavelength region such as an LED is used, a sensitizer is preferably combined in order to efficiently generate radicals from the photoinitiator and support the action of the photopolymerization initiator.
Further, the photoinitiating adjuvant is a secondary or tertiary amine compound having at least 1 hydrogen on the carbon at the α -position. The hydrogen on the carbon in the alpha position of these compounds is abstracted by the radical, so that the tertiary amine compound becomes an alpha-aminoalkyl radical. The alpha-aminoalkyl radical can efficiently initiate polymerization of the (meth) acrylate monomer. On the other hand, when the α -aminoalkyl radical reacts with oxygen in the air, oxygen radicals are generated and lose the polymerization initiating ability of the (meth) acrylate monomer, but the oxygen radicals can abstract hydrogen from the unreacted photo-initiation assistant to generate a new α -aminoalkyl radical that can initiate polymerization of the (meth) acrylate monomer. Therefore, deactivation of the photoinitiator by oxygen in the air can be suitably suppressed, and thus a combination of the photoinitiator aids is preferable. Further, when the active energy ray-curable ink is used for offset printing, it is more preferable to use a tertiary amine compound having a lower basicity to suppress excessive emulsification of the active energy ray-curable ink in order to suppress adhesion of the ink to the hydrophilic non-pattern portion.
Preferred photosensitizers are not particularly limited, but examples thereof include thioxanthone-based photosensitizers such as 4,4' -bis (diethylamino) benzophenone-based photosensitizers, anthraquinone-based photosensitizers, and coumarin-based photosensitizers.
Among these, particularly preferred are thioxanthone-based compounds such as 2, 4-diethylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2-chlorothioxanthone and 2-isopropylthioxanthone, and 4,4' -dialkylaminobenzophenones such as Michler's ketone and 4,4' -bis- (diethylamino) benzophenone; from the viewpoint of performance, safety, ease of availability, and the like, 2, 4-diethylthioxanthone, 2-isopropylthioxanthone, and 4,4' -bis- (diethylamino) benzophenone are particularly preferable.
The sensitizer is preferably in the range of 0.05 to 10% by mass, more preferably 0.1 to 7.0% by mass, relative to the total amount of the solid components of the ink. When the amount is less than 0.05% by mass, a sufficient effect of improving curability cannot be obtained, and when the amount exceeds 10% by mass, the cured coating film is discolored to a yellow color to such an extent that the hue of the cured coating film cannot be tolerated, a sensitizer is precipitated, or the fluidity of the ink is significantly deteriorated.
On the other hand, the tertiary amine is not particularly limited, but examples thereof include ethyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, N-dimethylbenzylamine, N-dimethylaniline, N-diethylaniline, N-dimethyl-p-toluidine, N-dihydroxyethylaniline, triethylamine, and N, N-dimethylhexylamine, which can reduce polymerization inhibition by oxygen, or react with thioxanthones activated by ultraviolet rays and 4,4' -dialkylaminobenzophenones to become active radical donors, thereby improving the curing performance of the ink. The tertiary amine is preferably used in combination within a range not impairing the printing performance of the active energy ray-curable ink of the present invention, and is preferably used in a range of 0.1 to 10% by mass, more preferably 0.1 to 5.0% by mass, based on the total amount of the solid components of the ink.
In addition, in applications requiring high hygiene, a high molecular weight compound in which a plurality of photosensitizers or tertiary amines are branched in 1 molecule with a polyhydric alcohol or the like may be suitably used.
(monomer having ethylenically unsaturated double bond)
The active energy ray-curable monomer and/or oligomer used in the present invention is not particularly limited as long as it is a monomer and/or oligomer used in the field of active energy ray-curable technology. Particularly preferred are active energy ray-curable monomers and/or oligomers having a (meth) acryloyl group, a vinyl ether group, or the like as a reactive group. The number of reactive groups and the molecular weight are not particularly limited, and the higher the number of reactive groups, the higher the reactivity, but the higher the viscosity and crystallinity, and the higher the molecular weight, the higher the viscosity, and therefore, the more suitable combinations can be used depending on the desired physical properties. For example, in order to obtain necessary physical properties such as adhesiveness to a printing substrate and flexibility of a film, it is preferable to use a combination of highly reactive active energy ray-curable monomers having 3 or more functional groups, either singly or in combination of monofunctional and 2-functional monomers, as appropriate, in order to obtain the desired physical properties such as adhesiveness to a printing substrate and flexibility of a film, depending on the application.
Specifically, for example, monofunctional (meth) acrylate, polyfunctional (meth) acrylate, polymerizable oligomer, and the like have been demonstrated in the lamp system, and can be used as they are in the ultraviolet light emitting diode system described in the present invention.
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, hexadecyl (meth) acrylate, octadecyl (meth) acrylate, isoamyl (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, nonylphenoxyethyltetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and dicyclopentanyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and the like.
Examples of the 2-or more-functional (meth) acrylate include 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, tricyclodecanedimethanol 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 and other diol di (meth) acrylates, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, di (meth) acrylate of tris (2-hydroxyethyl) isocyanurate, diol di (meth) acrylate obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of bisphenol A, diol di (meth) acrylate obtained by adding 2 moles of ethylene oxide or propylene oxide to 1 mole of bisphenol A, trimethylolpropane (meth) acrylate obtained by adding 2 or ethylene oxide to 1 mole of bisphenol A, trimethylolpropane (meth) acrylate obtained by adding ethylene oxide to 1 mole of ethylene oxide or glycerol, and polyoxyalkylene polyol poly (meth) acrylates such as pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol poly (meth) acrylate, triols of tri (meth) acrylates obtained by adding 3 or more moles of ethylene oxide or propylene oxide to 1 mole of glycerin, triols of di (meth) acrylates or tri (meth) acrylates obtained by adding 3 or more moles of ethylene oxide or propylene oxide to 1 mole of trimethylolpropane, and diols of di (meth) acrylates obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of bisphenol a.
Examples of the polymerizable oligomer include amine-modified acrylates such as amine-modified polyether acrylate, amine-modified epoxy acrylate, amine-modified aliphatic acrylate, amine-modified polyester acrylate, and amino (meth) acrylate; thiol-modified acrylates such as thiol-modified polyester acrylate and thiol (meth) acrylate; polyester (meth) acrylates, polyether (meth) acrylates, polyolefin (meth) acrylates, polystyrene (meth) acrylates, epoxy (meth) acrylates, urethane (meth) acrylates, and the like.
Further, as the active energy ray-curable monomer and/or oligomer, a 4-functional or higher (meth) acrylate is preferably used because it greatly contributes to improvement of curability and strength in printing applications on paper such as unbleached paper, coated paper, copperplate paper, molded paper, thin paper, and thick paper, and is preferably used in a range of 15 to 70 mass% with respect to the total amount of solid components of the ink. On the other hand, in the printing application to plastics, the adhesion between the substrate and the cured coating film is reduced as the crosslink density of the cured coating film increases, and therefore it is necessary to appropriately reduce the content of the 4-or more functional (meth) acrylate. In this case, the (meth) acrylate having 4 or more functional groups is preferably used in a range of 0 to 50% by mass based on the total amount of the solid components of the ink.
The active energy ray-curable ink of the present invention contains, as essential components, the monomer having the ethylenically unsaturated double bond and the photopolymerization initiator represented by the general formula (1), but in addition to these, a resin or a pigment; various additives.
(resin)
As the resin, various known and conventional binder resins can be used. The binder resin mentioned here is a resin having all suitable pigment affinity and dispersibility and having rheological properties required for printing ink, and examples of the non-reactive resin include diallyl phthalate resin obtained by polymerizing diallyl phthalate and/or diallyl isophthalate and/or diallyl terephthalate, epoxy resin, polyurethane resin, polyester resin, petroleum resin, rosin ester resin, poly (meth) acrylate, cellulose derivative, 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 polymerizable group in a molecule may be used, and these binder resins may be used alone or in combination of any 1 or more.
Among them, when the photopolymerization initiator represented by the general formula (1) is used in combination with the diallyl phthalate resin, the curability of the active energy ray-curable ink is improved, and the fluidity of the ink is improved, thereby suppressing the occurrence of poor printability such as a crack in a container on a printing press and transfer failure between ink rollers.
(pigment)
Examples of the pigment include known conventional organic pigments for coloring, and examples thereof include organic pigments for printing ink, which are disclosed 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, perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, thioindigo pigments, anthraquinophthalone pigments, metal complex pigments, diketopyrrolopyrrole pigments, carbon black pigments, and other polycyclic pigments.
In the active energy ray-curable ink of the present invention, inorganic fine particles may be used as the extender pigment. Examples of the inorganic fine particles include inorganic color pigments such as titanium oxide, graphite, and zinc white; inorganic pigments such as calcium carbonate powder, precipitated calcium carbonate, gypsum, clay (china clay), silica powder, diatomaceous earth, talc, kaolin, alumina white, barium sulfate, aluminum stearate, magnesium carbonate, barite powder, polishing powder, and other inorganic extender pigments, silicone, glass beads, and the like. These inorganic fine particles can be used in an amount of 0.1 to 60% by weight in the ink, whereby the rheological properties of the ink and the coloring can be adjusted.
(other additives)
Examples of the other additives include natural waxes such as carnauba wax, wood wax, lanolin, montan wax, paraffin wax, and microcrystalline wax, as additives for imparting friction resistance, anti-blocking property, sliding property, and anti-galling property; synthetic waxes such as fischer-tropsch wax, polyethylene wax, polypropylene wax, polytetrafluoroethylene wax, polyamide wax, and silicone compound.
Examples of the additive for imparting storage stability to the ink include polymerization inhibitors such as (alkyl) phenol, hydroquinone, catechol, resorcinol, p-methoxyphenol, t-butylcatechol, t-butylhydroquinone, pyrogallol, 1-trinitrophenylhydrazine, phenothiazine, p-benzoquinone, nitrosobenzene, 2, 5-di-t-butyl-p-benzoquinone, dithiobenzoyl disulfide, picric acid, cupferron, N-nitrosophenylhydroxylamine aluminum, tri-p-nitrophenylmethyl, N- (3-oxyanilino-1, 3-dimethylbutylidene) aniline oxide, dibutylcresol, cyclohexanone oxime cresol, guaiacol, o-isopropylphenol, butyraldehyde oxime, methyl ethyl ketoxime, and cyclohexanone oxime.
Further, additives such as an ultraviolet absorber, an infrared absorber, and an antibacterial agent may be added depending on the required performance.
The active energy ray-curable ink of the present invention can be used without a solvent, and an appropriate solvent can be used as needed. The solvent is not particularly limited as long as it does not react with each component, and 2 or more kinds thereof may be used alone or in combination.
The active energy ray-curable ink of the present invention can be produced by a method similar to the conventional method, for example, by rolling, 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 the other additives at room temperature to 100 ℃ using a kneader, a three-roll mill, an attritor, a sand mill, a gate mixer, or the like.
(method for producing cured ink, printed Material)
A second aspect of the present invention is a printed matter obtained by forming a layer of the active energy ray-curable ink on a substrate or a printing ink layer printed on a substrate and irradiating ultraviolet rays with an ultraviolet light emitting diode light source having a peak wavelength of 350 to 420 nm.
The printing substrate used in the printed matter of the present invention is not particularly limited, and examples thereof include paper such as wood-free paper, coated paper, molded paper, thin paper, and thick paper, films or sheets of polyester resin, acrylic resin, vinyl chloride resin, vinylidene chloride resin, polyvinyl alcohol, polyethylene, polypropylene, polyacrylonitrile, ethylene vinyl acetate copolymer, ethylene vinyl alcohol copolymer, ethylene methacrylic acid copolymer, nylon, polylactic acid, and polycarbonate, cellophane, aluminum foil, and other various substrates conventionally used as printing substrates.
The printing ink used for producing the printed matter of the present invention is not particularly limited as long as it is a composition that is suitably cured with respect to ultraviolet rays emitted from ultraviolet light emitting diodes, and, for example, an offset printing ink, an anhydrous printing ink, an intaglio printing ink, a flexographic printing ink, a screen printing ink, an inkjet printing ink, or other UV-curable printing inks conventionally used for printing applications can be used depending on the printing system.
The emission wavelength of the ultraviolet light emitted from the ultraviolet light emitting diode light source used for producing the printed matter of the present invention is preferably, for example, an emission peak wavelength of about 350 to 420 nm.
The cumulative light amount value of the ultraviolet ray irradiated from the ultraviolet light emitting diode light source to the UV curable composition differs depending on the kind of the UV curable composition on the printing substrate, the thickness of the printing layer, and the like, and therefore cannot be strictly specified, and preferable conditions, for example, the total cumulative light amount of 5 to 200mJ/cm, may be appropriately selected 2 About, more preferably 10 to 100mJ/cm 2 Left and right.
The accumulated light value is less than 5mJ/cm 2 Under the conditions (2), it is difficult to obtain sufficient curability, while the cumulative light quantity value exceeds 200mJ/cm 2 The condition (2) is not essential in the printing system of the present invention, and excessive energy irradiation is not performed for the purpose of maintaining energy saving property which is a characteristic of the ultraviolet light emitting diode light source.
The intensity of ultraviolet light (mW/cm) irradiated from an ultraviolet light-emitting diode light source to the UV-curable composition on the printing substrate 2 ) The number of ultraviolet light emitting diode light sources arranged in the printing direction and the irradiation distance from the light sources to the composition are appropriately determined according to the respective conditionsThe irradiation intensity range of (b) is not particularly limited since it varies, but since the moving speed of the printing substrate in the printing system of the present invention is about 60 to 400m/min, it is preferable that the integrated light quantity value is the irradiation intensity of the above-described level with respect to the UV curable composition on the printing substrate moving at the printing speed.
Examples
The present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
[ method for producing active energy ray-curable offset printing ink ]
The inks of examples 1 to 8 and comparative examples 1 to 10 were subjected to rolling with a three-roll mill in accordance with the compositions of tables 1 to 3, thereby obtaining various ink compositions. The blank column in the table means unmatched.
[ Process for producing a color-developed Material ]
The active energy ray-curable ink thus obtained was uniformly stretched on a rubber roll and a metal roll of a rotary ink tester using 0.10ml of ink using a simple developing machine (RI tester, manufactured by Fengroi Seiki Seisaku Co., ltd.), and on a PET raw material (DAITAC UVPET clear 25FL, manufactured by DIC Co., ltd.) so as to be about 220cm in length 2 The ink was uniformly spread over the entire area of (1.8) (measured by a SpectroEye densitometer, manufactured by X-Rite corporation) to prepare a developed color. The rotary ink tester is a tester for developing ink on paper or film, and can adjust the transfer amount of ink and the printing pressure.
(drying method Using ultraviolet light-emitting diode light Source)
The spread was placed on a belt conveyor using a UV irradiation apparatus (EYE GRAPHICS) equipped with a water-cooled UV-LED (output 100% of UV-LED with a central emission wavelength of 385 nm. + -. 5 nm) and the belt conveyor, and passed right under the LED at a speed of 100m/min of the conveyor (irradiation distance 9 cm). The spread obtained by applying the photocurable ink by the above method is irradiated with Ultraviolet (UV) light to cure and dry the ink film.
[ method for evaluating curability of photocurable printing ink ]
Immediately after curing, the cured ink layer was scratched with a fingernail to evaluate the curability of the cured film.
The evaluation criteria are as follows.
Very good: even if the coating was rubbed with a strong force, no scratch was caused, and the UV curability was very good.
O: slightly causing scars when scratched with strong force.
Δ: when rubbed with strong force, the scratch is obviously caused.
X: even when rubbed with a weak force, the scratch was clearly caused, and the UV curability was poor.
[ method for evaluating odor of cured coating film ]
The cured product cured by the above-described curing method was cut into pieces of 5cm in length and 2.5cm in width, and 10 pieces of the cut pieces were prepared. 10 pieces of the cut pieces were quickly put into a collection vial having an outer diameter of 40mm, a height of 75mm, an inner diameter of 20.1mm and a capacity of 50ml, and the collection vial was kept at 60 ℃ for 1 hour with a lid closed to fill the collection vial with odor. Next, the collection vial was allowed to stand to room temperature, and the strength of odor of each sample was evaluated in 10 stages by 10 monitors who evaluated the strength of odor.
The results of evaluation of the odor at the 10 positions were averaged to determine the strength of the odor of the sample. Further, a higher value means a weaker odor.
○：10～7
△：6～3
×：2～0
[ Table 1]
[ Table 2]
[ Table 3]
Details of the raw materials used are as follows:
"RAVEN 1060Ultra": CARBON black made from BIRLA CARBON
"FASTOGEN BLUE TGR-1": DIC fragment Blue 15: 3
"HOSTAPERM VIOLET RL 02": clariant Pigment Violet 23
"HI-FILER 5000PJ": talc produced in Songcun industry
"S-381-N1": olefin-based fine powder wax made by Shamrock
"diallyl phthalate resin varnish": mixture of DAISO-DAP 35 mass% dissolved in SR355NS 65 mass% made by OSAKA SODA
"STEARER TBH": refined chemical process of tert-butyl hydroquinone
"aronexi M-400": synthesis of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate in east Asia
"SR355NS": preparation of ditrimethylolpropane tetraacrylate from ARKEMA
"photopolymerization initiator a": (1) The photopolymerization initiator described above is a compound represented by the following structural formula, 2-benzyl-2-dimethylamino-1- (4-piperidinophenyl) -butan-1-one
[ chemical formula 3]
All of the following photopolymerization initiators are manufactured by IGM RESINS.
Omnirad 369 2-benzyl-2- (dimethylamino) -4' -morpholinobutyrylbenzene
Omnirad 907 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one
Omnirad TPO 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide
Omnirad 819 bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide
Omnirad DETX 2, 4-diethylthioxanthone
Omnirad EMK 4,4' -bis (diethylamino) benzophenone
Omnirad EDB 4- (dimethylamino) benzoic acid ethyl ester
As a result, it was found that the active energy ray-curable inks of examples 1 to 8 were excellent in curability.
Claims (7)
1. An active energy ray-curable ink comprising a monomer having an ethylenically unsaturated double bond, a diallyl phthalate resin, and a photopolymerization initiator represented by the general formula (1):
in the formula, n represents 0 or 1,R 1 ～R 4 Each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms.
2. The active energy ray-curable ink according to claim 1, wherein the photopolymerization initiator represented by the general formula (1) is 2-benzyl-2-dimethylamino-1- (4-piperidinophenyl) -butan-1-one.
3. The active energy ray-curable ink according to claim 1 or 2, which contains an acylphosphine oxide-based photoinitiator and/or a photosensitizer.
4. The active energy ray-curable ink according to claim 1 or 2, which contains a tertiary amine compound.
5. A method for producing a cured ink, characterized by printing using the active energy ray-curable ink according to any one of claims 1 to 4, and curing the printed ink using an active energy ray.
6. A method for producing a cured ink, characterized by performing offset printing using the active energy ray-curable ink according to any one of claims 1 to 4, and curing the printed ink using an active energy ray.
7. A printed matter obtained by the method for producing a cured ink according to claim 5 or 6.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018042924 | 2018-03-09 | ||
| JP2018-042924 | 2018-03-09 | ||
| PCT/JP2019/006471 WO2019171965A1 (en) | 2018-03-09 | 2019-02-21 | Actinic-ray-curable ink, method for producing cured ink, and printed matter |
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| CN111801393A CN111801393A (en) | 2020-10-20 |
| CN111801393B true CN111801393B (en) | 2022-10-18 |
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| Country | Link |
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| JP (1) | JP6861282B2 (en) |
| CN (1) | CN111801393B (en) |
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| WO (1) | WO2019171965A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61147596A (en) * | 1984-12-21 | 1986-07-05 | 大日本インキ化学工業株式会社 | Manufacture of double side through hole printed circuit board |
| DE3880868D1 (en) * | 1987-03-26 | 1993-06-17 | Ciba Geigy Ag | Neue alpha-aminoacetophenone als photoinitiatoren. |
| JPS63264686A (en) * | 1987-04-22 | 1988-11-01 | Toyo Ink Mfg Co Ltd | Resist ink |
| JPH02283486A (en) * | 1988-10-11 | 1990-11-20 | Ookurashiyou Insatsu Kyokucho | Multicolor printed matter which shows continuous change in print color, its printing method and printing mechanism |
| JP2764967B2 (en) * | 1988-12-05 | 1998-06-11 | 住友電気工業株式会社 | Coated optical fiber |
| JP4134017B2 (en) * | 2004-12-10 | 2008-08-13 | ケーニッヒ ウント バウエル アクチエンゲゼルシャフト | Newspaper printing machine |
| JP2006229127A (en) * | 2005-02-21 | 2006-08-31 | Showa Denko Kk | Thermosetting composition for solder resist and its curing object |
| JP5564144B1 (en) * | 2013-01-15 | 2014-07-30 | 太陽インキ製造株式会社 | Curable resin composition, dry film and cured product thereof, and printed wiring board using them |
| CN103926791B (en) * | 2013-01-15 | 2016-11-16 | 太阳油墨制造株式会社 | Hardening resin composition, its dry film and solidfied material and use their printed circuit board (PCB) |
| JP6317070B2 (en) * | 2013-05-07 | 2018-04-25 | 太陽ホールディングス株式会社 | Printed wiring board material and printed wiring board using the same |
| JP5523642B1 (en) * | 2013-07-26 | 2014-06-18 | 太陽インキ製造株式会社 | Photocurable composition for producing printed wiring board, cured product thereof and printed wiring board |
| JP6172484B1 (en) * | 2016-04-22 | 2017-08-02 | 東洋インキＳｃホールディングス株式会社 | Active energy ray-curable printing ink and printed matter |
| JP2018002958A (en) * | 2016-07-07 | 2018-01-11 | Dic株式会社 | Active energy ray-curable printing ink and printed matter of the same |
| GB2561985B (en) * | 2017-04-24 | 2021-07-07 | Fujifilm Speciality Ink Systems Ltd | LED-curable inkjet ink containing photoinitiator blend |
-
2019
- 2019-02-21 WO PCT/JP2019/006471 patent/WO2019171965A1/en active Application Filing
- 2019-02-21 JP JP2019532152A patent/JP6861282B2/en active Active
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| WO2019171965A1 (en) | 2019-09-12 |
| CN111801393A (en) | 2020-10-20 |
| TW201938710A (en) | 2019-10-01 |
| JP6861282B2 (en) | 2021-04-21 |
| JPWO2019171965A1 (en) | 2020-04-16 |
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