CN113956779B - Active energy ray-curable coating agent and coated building material using same - Google Patents
Active energy ray-curable coating agent and coated building material using same Download PDFInfo
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- CN113956779B CN113956779B CN202110770269.8A CN202110770269A CN113956779B CN 113956779 B CN113956779 B CN 113956779B CN 202110770269 A CN202110770269 A CN 202110770269A CN 113956779 B CN113956779 B CN 113956779B
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- meth
- acrylate
- coating agent
- active energy
- energy ray
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- 239000011248 coating agent Substances 0.000 title claims abstract description 135
- 239000004566 building material Substances 0.000 title claims description 17
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- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- URLYGBGJPQYXBN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound OCC1CCC(COC(=O)C=C)CC1 URLYGBGJPQYXBN-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- HZWAUDKTZOUQPD-UHFFFAOYSA-N diphenylphosphoryl-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 HZWAUDKTZOUQPD-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000010434 nepheline Substances 0.000 description 1
- 229910052664 nepheline Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 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 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000007921 spray 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
- 238000003756 stirring Methods 0.000 description 1
- 239000010435 syenite Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 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
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- 238000004804 winding Methods 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
Abstract
The present invention addresses the problem of providing an active energy ray-curable coating agent which, even without using an organic solvent, has both low gloss in the matte style, excellent print suitability without coating unevenness, and cellotap resistance. The active energy ray-curable coating agent contains a monofunctional (meth) acrylate monomer, a urethane (meth) acrylate which is a compound having a plurality of (meth) acryloyl groups, which is the reaction product of dicyclohexylmethane 4,4' -diisocyanate and a hydroxyl group-containing (meth) acrylate, and/or a (meth) acryloyl group-containing acrylic resin having a double bond equivalent weight of 100 to 1000 g/mol. Wherein (1) the monofunctional (meth) acrylate monomer is 10 to 60% by mass of the total amount of the curing component, (2) the urethane (meth) acrylate is 4 to 30% by mass of the total amount of the curing component, and (3) the acrylic resin is 0.1 to 20% by mass of the total amount of the curing component.
Description
Technical Field
The present invention relates to an active energy ray-curable coating agent for forming a surface protective layer of a decorative sheet for furniture, flooring materials, etc. facing the interior of a building such as a house, and a coated building material having a coating film formed from the active energy ray-curable coating agent.
Background
Conventionally, decorative sheets are often used for furniture, flooring materials, etc. in buildings such as houses, and the surface layers thereof are variously coated for protection and beauty. The decorative sheet is a general term for printed matter to be attached to a member such as wood and to decorate a surface.
In the field of building material interior, furniture, walls, ceilings, and floors are being replaced from so-called painting to sheeting in view of high design, good workability, low cost, and economy that can cope with small lot sizes of decorative sheets.
On the other hand, in the present situation, a polymer and an organic solvent are almost all used as a coating agent for forming a surface protective layer of a decorative sheet in China, and about 30 to 70% of the total amount of the coating agent is an organic solvent in terms of a solid content mass ratio, so that a large amount of evaporation of the organic solvent into the atmosphere during the coating process is unavoidable (for example, reference 1).
As one of the methods for reducing the amount of evaporation of the organic solvent into the atmosphere, that is, VOC, there is a solvent-free coating agent of a monomer main body, but in the case where the substrate is paper, there is a tendency that coating unevenness is liable to occur and good printing adaptability is difficult because a sufficiently uniform coating film is not formed due to rapid penetration into the paper substrate.
In addition, in order to exhibit a higher-level feel, the surface of a coated building material such as a recent decorative sheet is preferably a matte-type coated building material that tends to suppress gloss, while if an organic solvent is used, there is an advantage that silica or the like used in combination due to volatilization of the solvent is exposed from the film surface of the surface protective layer to obtain a low-gloss effect, but this mechanism cannot be adopted in the case of no solvent, and thus there is a disadvantage that it is easy to obtain a coating film with low gloss. The active energy ray-curable coating agent of the present invention can overcome these disadvantages even without using an organic solvent.
In addition, when the active energy ray-curable coating agent of the present invention is actually used for processing decorative sheets on a construction site, temporary fixing for a notice such as a memo or alignment may be performed on the decorative sheets using an adhesive tape, and the agent also has Cellotape (registered trademark) properties showing resistance of the surface of the decorative sheets when the temporary fixing tape is peeled off.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2018-184583
Disclosure of Invention
Problems to be solved by the invention
The present invention addresses the problem of providing an active energy ray-curable coating agent which, even without using an organic solvent, combines low gloss in the matte style, excellent print suitability without coating irregularities, and cellotap (registered trademark) resistance.
Means for solving the problems
The present invention relates to an active energy ray-curable coating agent, which is characterized by containing a monofunctional (meth) acrylate monomer and a specific urethane (meth) acrylate and/or a (meth) acryl-containing acrylic resin in specific amounts in total of curing components.
That is, the present invention relates to an active energy ray-curable coating agent comprising: a monofunctional (meth) acrylate monomer, a urethane (meth) acrylate which is a compound having a plurality of (meth) acryloyl groups, which is a reaction product of dicyclohexylmethane 4,4' -diisocyanate and a hydroxyl group-containing (meth) acrylate, and/or a (meth) acryloyl group-containing acrylic resin having a double bond equivalent weight of 100 to 1000g/mol,
(1) The monofunctional (meth) acrylate monomer is 10 to 60 mass% of the total amount of the curing component,
(2) The urethane (meth) acrylate which is the reaction product of dicyclohexylmethane 4,4' -diisocyanate and the hydroxyl group-containing (meth) acrylate is 4 to 30% by mass based on the total amount of the curing component,
(3) The (meth) acryloyl group-containing acrylic resin having a double bond equivalent of 100 to 1000g/mol is 0.1 to 20% by mass based on the total amount of the curing component.
The present invention also relates to an active energy ray-curable coating agent, wherein the monofunctional (meth) acrylate monomer has a number average molecular weight in the range of 100 to 1000.
In the active energy ray-curable coating agent according to the present invention, the (meth) acryl-containing acrylic resin has a glass transition temperature (Tg) in the range of 40 to 130 ℃ and a hydroxyl value in the range of 5 to 300mgKOH/g.
The active energy ray-curable coating agent according to the present invention further contains a (meth) acrylate monomer having 2 or more functions.
The active energy ray-curable coating agent according to the present invention further contains silicone epoxy (meth) acrylate.
The active energy ray-curable coating agent according to the present invention does not contain a volatile organic solvent having a boiling point of less than 260 a under atmospheric pressure.
The present invention also relates to a coated building material having a coating film formed from the active energy ray-curable coating agent.
ADVANTAGEOUS EFFECTS OF INVENTION
The active energy ray-curable coating agent of the present invention can provide a coated building material having both low gloss in matte style, excellent printing suitability and Cellotape (registered trademark) resistance.
Detailed Description
The active energy ray-curable coating agent of the present invention is characterized by comprising: the reactive energy ray-curable coating agent comprises a monofunctional (meth) acrylate monomer, a urethane (meth) acrylate which is a compound having a plurality of (meth) acryloyl groups, and/or a (meth) acryloyl group-containing acrylic resin having a double bond equivalent weight of 100 to 1000g/mol, wherein the urethane (meth) acrylate is a reaction product of dicyclohexylmethane 4,4' -diisocyanate and a hydroxyl group-containing (meth) acrylate,
(1) The monofunctional (meth) acrylate monomer is 10 to 60 mass% of the total amount of the curing component,
(2) The urethane (meth) acrylate which is the reaction product of dicyclohexylmethane 4,4' -diisocyanate and the hydroxyl group-containing (meth) acrylate is 4 to 30% by mass based on the total amount of the curing component,
(3) The (meth) acryloyl group-containing acrylic resin having a double bond equivalent of 100 to 1000g/mol is 0.1 to 20% by mass based on the total amount of the curing component.
In the present invention, the term "curing component" means an active energy ray-curable component contained in the active energy ray-curable coating agent of the present invention, specifically, a monofunctional (meth) acrylate monomer, a urethane (meth) acrylate which is a compound having a plurality of (meth) acryloyl groups, and/or an acrylic resin containing a (meth) acryloyl group and having a double bond equivalent weight of 100 to 1000g/mol, and all components of other active energy ray-curable compounds which are contained as needed, and does not include a photopolymerization initiator or an active energy ray-non-curable compound, and the urethane (meth) acrylate is a reaction product of dicyclohexylmethane 4,4' -diisocyanate and a hydroxyl group-containing (meth) acrylate. The "total amount of the curing component" means the total mass of all the components.
The (meth) acrylate monomer used in the active energy ray-curable coating agent of the present invention will be described.
In the present invention, "(meth) acrylate" means one or both of acrylate and methacrylate.
Examples of the monofunctional (meth) acrylate include ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isopentyl (meth) acrylate, isodecyl (meth) acrylate, isostearyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, nonylphenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, glycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, diethylaminoethyl (meth) acrylate, nonylphenoxyethyl tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, ethoxyethoxyethanol acrylic acid polymer esters, and the like.
Among them, the above ethoxyethoxyethanol acrylic acid polymer ester is preferable, and specifically, α -acryl- ω - (3, 6-dioxaoct-1-yloxy) poly (oxyethylene carbonyl) is most preferable.
The content of the monofunctional (meth) acrylate is preferably 10 to 60% by mass, more preferably 15 to 55% by mass, based on the total amount of the curing component in the coating agent, from the viewpoint of suitable coating property and curability of the coating surface.
When the content of the monofunctional (meth) acrylate is 10 mass% or more based on the total amount of the curing components, a sufficiently low gloss tends to be obtained, and when it is 60 mass% or less, a sufficiently curability tends to be obtained.
Next, the urethane (meth) acrylate used in the active energy ray-curable coating agent of the present invention will be described. In the present invention, "urethane (meth) acrylate" means one or both of urethane acrylate and urethane methacrylate.
The urethane acrylate used in the active energy ray-curable coating agent of the present invention is necessarily a reaction product of dicyclohexylmethane 4,4' -diisocyanate and a hydroxyl group-containing (meth) acrylate.
Examples of the hydroxyl group-containing (meth) acrylate include hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, 1, 4-cyclohexanedimethanol monoacrylate, polyethylene glycol monomethacrylate, trimethylolpropane diacrylate, trimethylolpropane dimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethylacrylate, glycidyl acrylate, and glycidyl methacrylate.
The content of the urethane (meth) acrylate is preferably 4 to 30% by mass based on the total amount of the curing component in the coating agent, particularly preferably 5 to 30% by mass in terms of preventing coating unevenness due to rapid inhalation to the paper substrate, from the viewpoint of suitable coating property and curability of the coated surface.
If the content of urethane (meth) acrylate is 4 mass% or more of the total amount of the curing components in the coating agent, there is a tendency that sufficient printing compatibility is obtained, and if it is 30 mass% or less, there is a tendency that increase in viscosity is suppressed and coating property is sufficiently maintained.
Next, the (meth) acryloyl group-containing acrylic resin having a double bond equivalent weight of 100 to 1000g/mol used in the active energy ray-curable coating agent of the present invention will be described.
The (meth) acryl-containing acrylic resin used in the present invention is not particularly limited, and an acrylic resin obtained by a known method can be used.
Specifically, for example, a method of blending a carboxyl group-containing polymerizable monomer such as acrylic acid or methacrylic acid, an amino group-containing polymerizable monomer such as dimethylaminoethyl methacrylate or dimethylaminopropyl acrylamide as the copolymerization component, copolymerizing the monomers to obtain the copolymer having a carboxyl group or an amino group, and then reacting the carboxyl group or the amino group with a monomer having a glycidyl group and a (meth) acryloyl group such as glycidyl methacrylate; a method comprising copolymerizing a hydroxyl group-containing monomer such as 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate as the copolymerization component to obtain the copolymer having a hydroxyl group, and then reacting the hydroxyl group with a monomer having an isocyanate group and a (meth) acryloyl group such as isocyanatoethyl methacrylate; a method comprising blending a polymerizable monomer having a glycidyl group such as glycidyl methacrylate as the copolymerization component in advance, copolymerizing the polymerizable monomer to obtain the copolymer having a glycidyl group, and then reacting the glycidyl group with a polymerizable monomer having a carboxyl group such as acrylic acid or methacrylic acid; a method in which a carboxyl group is introduced into the terminal of a copolymer by using thioglycollic acid as a chain transfer agent during polymerization, and a monomer having a glycidyl group and a (meth) acryloyl group such as glycidyl methacrylate is reacted with the carboxyl group; and a method in which a carboxyl group is introduced into a copolymer using a carboxyl group-containing azo initiator such as azobiscyanopentanoic acid as a polymerization initiator, and a monomer having a glycidyl group and a (meth) acryloyl group such as glycidyl methacrylate is reacted with the carboxyl group.
Among them, a method of copolymerizing a carboxyl group-containing monomer such as acrylic acid or methacrylic acid or an amino group-containing monomer such as dimethylaminoethyl methacrylate or dimethylaminopropyl acrylamide in advance and reacting the carboxyl group or amino group with a monomer having a glycidyl group and a (meth) acryloyl group such as glycidyl methacrylate or a method of copolymerizing a glycidyl group-containing polymerizable monomer such as glycidyl methacrylate in advance as the above-mentioned copolymerization component to obtain the above-mentioned copolymer having a glycidyl group and then reacting the glycidyl group with a carboxyl group-containing polymerizable monomer of acrylic acid or methacrylic acid is preferable in the most simple manner.
Examples of the monomer component constituting the (meth) acryl-containing acrylic resin used in the present invention include monofunctional monomers such as ethyl (meth) acrylate, ethylhexyl (meth) acrylate, styrene, methyl styrene, and N-vinylpyrrolidone, and polyfunctional monomers such as trimethylolpropane (meth) acrylate, hexanediol (meth) acrylate, tripropylene glycol di (meth) acrylate, diethylene glycol (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol (meth) acrylate, and the like.
The double bond equivalent weight of the acrylic (meth) acrylate resin must be in the range of 100 to 1000 g/mol. When the double bond equivalent of the acrylic (meth) acrylate is 100g/mol or more, the volume shrinkage at the time of curing can be suppressed from becoming large, breakage due to bending or strain of the coating film is less likely to occur, and the workability tends to be less likely to occur due to tight crosslinking. Further, if 1000g/mol or less, the reactive group is not insufficient, and physical properties such as hardness after the reaction are sufficient, and if 200 to 600g/mol, more preferably 200 to 400g/mol, still more preferably.
The double bond equivalent weight of the (meth) acryl-containing acrylic resin is defined by the following formula.
"double bond equivalent" = "molecular weight of (meth) acryl-containing acrylic resin 1 molecule"/"number of double bonds"
The weight average molecular weight of the (meth) acryloyl group-containing acrylic resin is preferably in the range of 10000 to 100000. If the weight average molecular weight of the (meth) acryl-containing acrylic resin is 10000 or more, the coating film is less likely to remain tacky, and it is easy to simply make the coating film tack-free by the drying step, and if it is 100000 or less, the viscosity of the active energy ray-curable building material coating material is not excessively high, and the problem that the dilution at the time of coating is excessively effective and a sufficient coating amount cannot be obtained can be avoided. From the viewpoint of workability, the range of 10000 to 50000 is more preferable, and the range of 10000 to 30000 is still more preferable.
The weight average molecular weight refers to a value obtained by measurement in terms of polystyrene by GPC.
The content of the (meth) acryl-containing acrylic resin is preferably 0.1 to 20 mass% based on the total amount of the curing component in the coating agent, and more preferably 0.5 to 20 mass% from the viewpoint of preventing coating unevenness due to rapid penetration into the paper substrate, from the viewpoint of suitable coatability and curability of the coated surface.
If the content of the (meth) acryl-based acrylic resin is 0.1 mass% or more of the total amount of the curing components in the coating agent, there is a tendency that sufficient printing suitability can be obtained, and if it is 20 mass% or less, there is a tendency that an increase in viscosity is suppressed and coating property is sufficiently maintained.
The glass transition temperature (Tg) of the (meth) acryl-containing acrylic resin is preferably in the range of 40 to 130 ℃, and if it is 40 ℃ or higher, sufficient strength can be obtained after curing when a coating film is formed, and if it is 130 ℃ or lower, the tendency of brittleness and workability to be lowered when a coating film is formed can be suppressed. The hydroxyl value of the acrylic (meth) acrylate is preferably in the range of 5 to 300mgKOH/g, and if it is 5mgKOH/g or more, the dispersion of a matting agent such as silica used in combination tends not to be lowered and the gloss tends to be kept low, and if it is 300mgKOH/g or less, the tendency of lowering of the stain resistance can be suppressed.
The glass transition temperature (Tg) is measured by scanning with a differential scanning calorimeter under a nitrogen atmosphere using a cooling device at a temperature ranging from-80 to 450℃and a temperature rise of 10℃per minute.
In addition, in the active energy ray-curable coating agent of the present invention, a (meth) acrylate having 2 or more functions may be used in combination in addition to the monofunctional (meth) acrylate monomer. By using a (meth) acrylate having 2 or more functions in combination with the monofunctional (meth) acrylate monomer, the appearance of the coating film can be maintained, and high strength can be obtained as compared with the case where only a monofunctional monomer is used. The polymerizable oligomer may be further used in combination as required.
Examples of the 2-functional (meth) acrylate include 2-membered-diol di (meth) acrylate such as 1, 4-butanediol di (meth) acrylate, 3-methyl-1, 5-pentanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 2-methyl-1, 8-octanediol di (meth) acrylate, 2-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, tri (2-hydroxyethyl) isocyanurate di (meth) acrylate, ethylene oxide or propylene oxide di (meth) acrylate obtained by adding 4 moles or more to 1 mole of neopentyl glycol, ethylene oxide or propylene oxide di (meth) acrylate obtained by adding 2 moles of ethylene oxide to 1 mole of bisphenol a, and the like.
Examples of the above 3-functional or higher (meth) acrylate include a poly (meth) acrylate of a 3-membered or higher polyol such as trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, and dipentaerythritol poly (meth) acrylate, a tri (meth) acrylate of a triol obtained by adding 3 or more moles of ethylene oxide or propylene oxide to 1 mole of glycerin, a di-or tri (meth) acrylate of a triol obtained by adding 3 or more moles of ethylene oxide or propylene oxide to 1 mole of trimethylolpropane, and a poly (meth) acrylate of a polyoxyalkylene polyol such as a diol obtained by adding 4 or more moles of ethylene oxide or propylene oxide to 1 mole of bisphenol a.
Further, a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate (sometimes omitted as DPHA), ditrimethylolpropane tetraacrylate (sometimes omitted as DTMPTA), trimethylolpropane ethylene oxide adduct tri (meth) acrylate which is a tri (meth) acrylate of triol obtained by adding 3 mol or more of ethylene oxide to 1 mol of trimethylolpropane, and the like can be used. As a representative example of the trimethylolpropane ethylene oxide adduct tri (meth) acrylate, trimethylolpropane Ethylene Oxide (EO) -modified (n.apprxeq.3) triacrylate is given.
The total amount of the monofunctional (meth) acrylate and the (meth) acrylate having a function of 2 or more is preferably in the range of 60 to 80% by mass, more preferably 65 to 75% by mass, based on the total amount of the curing components in the coating agent.
The polymerizable oligomer may be further used in combination as required. Examples of the polymerizable oligomer include amine-modified polyether acrylates, amine-modified epoxy acrylates, amine-modified aliphatic acrylates, amine-modified polyester acrylates, amine (meth) acrylates, and other amine-modified acrylates, polyester (meth) acrylates, polyether (meth) acrylates, polyolefin (meth) acrylates, polystyrene (meth) acrylates, and epoxy (meth) acrylates.
The silica used in the active energy ray-curable coating agent of the present invention is more preferably amorphous silica. Examples of the amorphous silica include diatomaceous earth and activated clay, and among amorphous silica, dry silica, wet silica, silica gel, and the like can be used as synthetic amorphous silica.
As the silica used as the matting agent used in the coating agent, wet silica produced by neutralization reaction of an aqueous sodium silicate solution with an acid or alkali metal salt is preferable.
In the synthetic amorphous silica, primary particles of 5 to 55nm, which are the smallest structural units of the substance, are fused or chemically bonded to form a primary particle aggregate (secondary particle structure). The primary particle aggregates are physically aggregated and exist as secondary aggregates, but the secondary aggregates can be dispersed as primary particle aggregates (secondary particle structure) by applying physical shear force to various media. The average particle diameter of the present invention means an average secondary particle diameter as a primary particle aggregate (secondary particle structure).
The average particle diameter of the wet silica used as the matting agent is preferably 0.1 to 25. Mu.m, more preferably 0.3 to 20. Mu.m, still more preferably 0.5 to 15. Mu.m, and still more preferably 1 to 10. Mu.m. If the average particle diameter is less than 0.05. Mu.m, the primary particles having smaller particle diameters are strongly bonded, and the specific surface area is also increased, so that the coating agent has high oil absorption performance, sufficient fluidity is not obtained when the coating agent is prepared, and a high-quality feeling accompanied by a matte effect is not obtained due to a reduction in the matting effect. In addition, if the average particle diameter is larger than 25 μm, deterioration of the contamination property due to the irregularities of the dirt entering the surface and change of gloss and damage due to the falling off/burying of the particles are liable to occur.
The pore volume of the wet silica is preferably 0.1 to 2.0mL/g, more preferably 1.5 to 2.0mL/g. The apparent specific gravity is preferably 0.1 to 1.5g/mL, more preferably 0.1 to 0.5g/mL. The oil absorption is preferably 50 to 400mL/100g, more preferably 100 to 400mL/100g. When the pore volume is 0.1mL/g or more, the apparent specific gravity is 0.1g/mL or more, and the oil absorption is 50mL/100g or more, a sufficient matting effect can be obtained. Conversely, if the pore volume is 2.0mL/g or less, the apparent specific gravity is 1.5g/mL or less, and the oil absorption is 400mL/100g or less, the matting effect can be maintained, and the thickening effect is suppressed from increasing to a necessary level or more, without impairing the fluidity as a coating agent, which is preferable.
The content of the wet silica used as the matting agent in the present invention is preferably 0.01 to 20% by mass, more preferably 0.05 to 10% by mass, based on the total amount of the coating agent. When the silica content is 0.01 mass% or more, a sufficient matting effect can be obtained, and when it is 20 mass% or less, deterioration of fluidity and transferability as a coating agent is suppressed, which is preferable. Among them, a BET-based specific surface area of 50 to 500m is preferable 2 Wet silica/g.
Further, as the scratch resistance improving additive for imparting scratch resistance, acrylic beads, silicone beads, glass beads, or the like may be added. If resin beads as scratch resistance improving additives are further added to the wet silica as the matting agent, the scratch resistance of the coated surface can be improved in addition to moderately low gloss. Among them, acrylic beads are preferable.
The average particle diameter of the beads as the scratch resistance improving additive is 1 to 50. Mu.m, preferably 1 to 30. Mu.m, more preferably 1 to 15. Mu.m, and the content thereof is preferably 3 to 20% by mass, and even more preferably 5 to 15% by mass, based on the total amount of the coating agent. If the content of the beads is less than 3 mass%, a sufficient scratch resistance effect is not observed, and if it exceeds 20 mass%, the beads tend to be easily detached from the surface of the coating film, which is not preferable.
Further, as the scratch resistance improving additive for imparting scratch resistance, silica may be added. As the silica added to impart scratch resistance, a dry silica produced by burning a silicon tetrachloride gas or the like in a gas phase is preferable. If dry silica as a scratch resistance improving additive is further added to the wet silica as the matting agent, the scratch resistance of the coated surface can be improved in addition to moderately low gloss. The dry silica as the scratch resistance improving additive has an average particle diameter of 0.1 to 3. Mu.m, preferably 0.1 to 0.5. Mu.m, more preferably 0.1 to 0.25. Mu.m, and the content thereof is preferably 10 to 30% by mass, and even more preferably 15 to 20% by mass, based on the total amount of the coating agent. If the silica content is less than 10 mass%, a sufficient scratch resistance effect is not observed, and if it exceeds 30 mass%, the sharpness and the pollution properties as the coating agent tend to be impaired, which is not preferable.
Among them, a BET-based specific surface area of 50 to 500m is preferable 2 Dry silica/g.
The wet silica used as the matting agent used in the present invention and the dry silica used as the scratch resistance improving additive may be both surface-modified.
The method for surface-treating the silica particles is not particularly limited as long as it is a known method. Examples of the silica particles include silica particles surface-treated with wax and a silane coupling agent.
In addition, in the active energy ray-curable coating agent of the present invention, the addition of inorganic particles and/or organic particles can provide a cured coating film having a low gloss and further excellent scratch resistance. The inorganic particles are preferably talc, nepheline syenite, mica, bentonite, diatomaceous earth, calcium carbonate, alumina white, or the like, in addition to the silica, the organic particles are preferably polyethylene wax, polypropylene wax, acrylic bead pigment, or urethane bead pigment, and a plurality of inorganic/organic particles may be used in combination without distinction.
In addition, silicone (meth) acrylate, which is (meth) acrylate having a silicone skeleton, may be added to the active energy ray-curable coating agent of the present invention for the purpose of improving cellotap (registered trademark) resistance, and among them, silicone epoxy (meth) acrylate is preferable.
Examples of the commercial products of the silicone epoxy (meth) acrylate include Rad2011, rad2100 (silicone acrylate Cas No. 125445-52-9), rad2500 (polydimethylsiloxane acrylate Cas No. 125445-52-9), and Rad2700 (acrylic modified silicone Cas No. 157811-87-5) of the "Tego (registered trademark)" series manufactured by Evonik Japan, and particularly preferably Rad2700.
The amount of the silicone (meth) acrylate to be added is preferably in the range of 0.1 to 10% by mass, more preferably in the range of 0.3 to 8% by mass, based on the total amount of the coating agent. When the amount is 0.1% by mass or more, the adhesion of the coating agent to the surface of the coated building material and the Cellotap (registered trademark) resistance can be maintained. If it is 10 mass% or less, the tendency of easy back movement (japanese throttle) can be suppressed.
As the curing agent used in the active energy ray-curable coating agent of the present invention, a publicly known and commonly used photopolymerization initiator can be used, and among them, a radical polymerization type photopolymerization initiator is preferable, and examples thereof include α -hydroxyalkylketone type photopolymerization initiators which are free from coloring of a solution when the active energy ray-curable compound is dissolved and cause less yellowing with time. Examples of the α -hydroxyalkyl ketone photopolymerization initiator include 1-phenyl-2-hydroxy-2-methylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, and 1-hydroxycyclohexylphenyl ketone. In addition, a phenylacetaldehyde (phenyl glyoxolate) photopolymerization initiator is also preferable. Examples of the phenylglyoxylate photopolymerization initiator include methyl benzoate and the like. Among them, 1-hydroxycyclohexyl phenyl ketone is preferable.
As the photopolymerization initiator of the other radical polymerization type, monoacylphosphine oxide photopolymerization initiators having an absorption wavelength in the long wavelength region in ultraviolet rays may be used in combination as appropriate. Examples of the monoacylphosphine oxide-based photopolymerization initiator include monoacylphosphine oxides such as 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 2, 6-dimethoxybenzoyl-diphenylphosphine oxide, 2, 6-dichlorobenzoyl-diphenylphosphine oxide, 2,4, 6-trimethylbenzoyl-methylphosphinate, 2-methylbenzoyl-diphenylphosphine oxide, and isopropyl pivaloylphenylphosphinate, in addition to bisacylphosphine oxides which are colored when dissolved in an active energy ray-curable compound, and particularly, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide has a UV absorption wavelength which matches the emission wavelength region of UV-LEDs having emission wavelengths of 385nm and 395nm, whereby suitable curability can be obtained and yellowing of a cured coating film is reduced, which is more preferable from the viewpoint of being less.
The photopolymerization initiators may be used alone or in combination of 2 or more. The total amount of the photopolymerization initiator is preferably in the range of 0.1 to 20 mass% relative to the total amount of the coating agent. When the amount is 0.1 mass% or more, good curability can be obtained, and when the amount is 20 mass% or less, the amount of the initiator is not excessive, fluidity as a coating agent can be maintained, and workability are not deteriorated.
In addition, the curing speed can be increased by adding a tertiary amine compound selected from the group consisting of aliphatic amine derivatives and/or benzoic amine derivatives as a sensitizer. Tertiary amine compounds are known to increase reactivity and prevent reaction inhibition by oxygen. Preferred tertiary amine compounds include, for example, free alkylamines such as triethylamine, methyldiethanolamine and triethanolamine, aromatic amines such as 2-ethylhexyl-4-dimethylaminobenzoate and ethyl-4-dimethylaminobenzoate, and active energy ray-polymerizable compounds such as polymer-unsaturated amines (for example, (meth) acrylated amines), which have low odor and low volatility and are preferably capable of inhibiting yellowing by virtue of their ability to be incorporated into a polymer matrix by curing.
The tertiary amine compound may be used in an amount of preferably 0.1 to 10% by mass, more preferably 0.3 to 3% by mass, relative to the total amount of the coating material containing the organic solvent.
Further, as an optional component, wax, plasticizer, dispersant, defoamer, and the like may be contained as necessary.
The active energy ray-curable coating agent of the present invention is more preferably free of a highly volatile organic compound (VVOC) having a boiling point of 50 ℃ or less and a Volatile Organic Compound (VOC) having a boiling point of 50 to 260 ℃ under normal pressure.
For the purpose of thoroughly reducing the amount of evaporation of the organic solvent into the atmosphere, that is, reducing VOC, it is preferable that the organic solvent be free of any of the following aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-hexane and cyclohexane, esters such as ethyl acetate, butyl acetate and propyl acetate, alcohols such as methanol, ethanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, and alkylene glycol monoalkyl ethers such as ethylene glycol monoethyl ether and propylene glycol monomethyl ether.
(production of active energy ray-curable coating agent)
The active energy ray-curable coating agent of the present invention can be produced by: urethane (meth) acrylate, which is a reaction product of dicyclohexylmethane 4,4' -diisocyanate and hydroxyl group-containing (meth) acrylate, and/or acrylic (meth) acrylate having a double bond equivalent of 100 to 1000g/mol and a weight average molecular weight of 10000 to 100000, a monofunctional or 2-functional or more acrylic resin, a photopolymerization initiator, silica, if necessary, silicone epoxy (meth) acrylate, wax, other various additives, and the like are mixed, kneaded and dispersed.
The active energy ray-curable coating agent of the present invention can be adjusted by appropriately adjusting the size of the pulverization medium of the dispersing machine, the filling rate of the pulverization medium, the dispersion treatment time, and the like. As the dispersing machine, a roll mill, a ball mill, a pebble mill, an attritor, a sand mill, or the like, which is commonly used, can be used.
When unexpected coarse particles or the like are contained in the coating agent, the coating material is preferably removed by filtration or the like because the quality of the coated article is reduced. The filter may be a conventionally known filter.
The base material using the active energy ray-curable coating agent of the present invention includes, in addition to paper and various films for decorative sheets, wood, nonflammable materials, and the like.
In particular, the active energy ray-curable coating agent of the present invention can provide good printing suitability without coating unevenness by suppressing rapid permeability to a paper substrate.
The decorative sheet is composed of the following components: the active energy ray-curable coating agent of the present invention forms a pattern layer by printing or coating a known substrate such as paper or film with, for example, an acrylic, cellulose, vinyl, chlorinated polyolefin, chlorinated rubber, urethane-based printing ink or paint, and then providing a top coat layer covering the pattern layer.
Examples of the type of the base material facing the decorative sheet include paper sheets such as tissue paper, plain paper, reinforced paper, and resin impregnated paper, titanium paper, polyethylene terephthalate sheets, glycol-modified polyethylene terephthalate sheets (PETG sheets), polyvinyl chloride sheets, polyethylene sheets, resin sheets such as acrylonitrile butadiene styrene sheets, and polypropylene sheets, and composite sheets thereof.
The wood base material of the wood decorative board includes known base materials such as plywood, chipboard, hard board, and MDF, which have been conventionally used as wood base materials of decorative boards, furniture, and building members. In addition, it is irrelevant by which process these known substrates are obtained.
Examples of the incombustible material that can be used as a base material include gypsum board, and perforated plate building materials using gypsum board, calcium silicate board, and the like as raw materials.
Taking a decorative sheet using the active energy ray-curable coating agent of the present invention as an example, a coated building material is produced by the following steps: the coating film of the coating agent is produced by printing or coating the substrate with a known printing ink or paint such as acrylic, cellulose, vinyl, chlorinated polyolefin, chlorinated rubber, urethane, or the like to form a pattern layer, and then applying the active energy ray-curable coating agent.
In producing a coating film using the above active energy ray-curable coating agent, specific examples of the coating/printing system of the building material coating material include roll coaters, gravure coaters, flexographic coaters, air knife coaters, doctor blade coaters, air knife coaters, extrusion coaters, dip coating machines, transfer roll coaters, kiss coaters, curtain coaters, casting coaters, spray coaters, die coaters, offset printers, screen printers, and the like, as the coating method.
Next, the coating film obtained in the above step is irradiated with light of 30 to 1000mJ/cm 2 At least 1 time, and can provide a coated building material excellent in surface curability.
If the active energy ray-curable coating agent is irradiated with active energy rays in a gas atmosphere having an oxygen concentration of less than 8% by injecting a mixed gas of 1 or 2 or more selected from nitrogen gas, carbon dioxide gas, and argon gas into the reaction vessel together with air or separately, the curing of the coating film obtained in the above step can be performed more efficiently.
The ratio of 30-1000 mJ/cm 2 The active energy rays of (a) are ionizing radiation such as ultraviolet rays, electron beams, and gamma rays, electromagnetic waves, and the like, and ultraviolet rays or electron beams are preferable.
In the case of irradiating ultraviolet rays under a gas atmosphere having an oxygen concentration of less than 8%, a known ultraviolet irradiation device including a high-pressure mercury lamp, an excimer lamp, a metal halide lamp, and the like can be used. If the ultraviolet ray quantity at the time of curing is 30mJ/cm 2 The curing efficiency is good, and the curing efficiency is 1000mJ/cm 2 Hereinafter, it is preferable from the viewpoint of preventing damage to the substrate due to heat.
The active energy ray-curable coating agent of the present invention can be prepared into a cured coating film by irradiation of active energy rays after application to a substrate. Examples of the active energy rays include ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays, and specific energy sources and curing devices include germicidal lamps, ultraviolet fluorescent lamps, ultraviolet light emitting diodes (UV-LEDs), carbon arcs, metal halide lamps, xenon lamps, chemical lamps, low-pressure mercury lamps, high-pressure mercury lamps for copying, medium-pressure or high-pressure mercury lamps, ultrahigh-pressure mercury lamps, electrodeless lamps, metal halide lamps, natural light, scanning type electron beam accelerators, and the like.
In the active energy ray-curable coating agent of the present invention, the irradiation with the active energy rays, preferably ultraviolet rays or the like, as described above, allows the curing reaction to proceed without leaving tackiness at the time of completion even if the agent is not a two-component curing type. For example, commercial products such as H lamp, D lamp, and V lamp manufactured by fusion system can be used.
In the curing in the inert gas, the curing inhibition by oxygen is small, and the urethane (meth) acrylate which is the reaction product of the dicyclohexylmethane 4,4' -diisocyanate and the hydroxyl group-containing acrylate, and/or the radical polymerizable double bond of the main agent such as the acrylic (meth) acrylate having a double bond equivalent of 100 to 1000g/mol and a weight average molecular weight of 10000 to 100000 further proceeds, and the curing is sufficiently performed, and the curing stays on the surface layer for a long period of time even if the time passes, so that the resistance of the coating film surface of the decorative sheet increases, and the adhesion can be further improved. The sufficiently fixed additive component is not easily detached even when it is brought into contact with the back surface of the original sheet during winding of a roll in gravure printing, for example.
The active energy ray-curable coating agent of the present invention can be widely used not only for building materials but also for surface coating applications such as furniture, musical instruments, office supplies, sporting goods, toys, and the like.
[ example ]
Hereinafter, the present invention will be described in more detail with reference to examples. In the following examples, parts and mass parts represent mass%.
The measurement of the weight average molecular weight (in terms of polystyrene) by GPC in the present invention was performed under the following conditions using HLC8220 system manufactured by eastern co.
Separation column: 4 TSKgelGMHHR-N manufactured by Tosoh corporation was used.
Column temperature: 40 ℃.
Mobile phase: and tetrahydrofuran, manufactured by Wako pure chemical industries, ltd.
Flow rate: 1.0 ml/min.
Sample concentration: 1.0 wt%.
Sample injection amount: 100 microliters.
A detector: differential refractometer.
Further, the glass transition temperature (Tg) was measured as follows: scanning was performed using a differential scanning calorimeter (DSC Q100, manufactured by TA Instruments, inc.) under a nitrogen atmosphere using a cooling device at a temperature ranging from-80 to 450℃and a temperature rise of 10℃per minute.
The hydroxyl value of the acrylic (meth) acrylate is a value calculated by back titration of the residual acid base when the hydroxyl groups in the resin are acetylated with an excessive amount of an acetyl reagent, and the hydroxyl value in 1g of the resin is expressed in mg of potassium hydroxide (KOH), based on JISK 0070.
The average particle diameter of the silica was measured using a nanoparticle size distribution measuring instrument Nanotrac UPAEX-150 manufactured by diutan corporation.
(preparation of active energy ray-curable coating agent)
[ example 1 ]
Urethane (meth) acrylate as a reaction product of dicyclohexylmethane 4,4' -diisocyanate and hydroxyl group-containing (meth) acrylate (number average molecular weight: 5000) 2 parts of an ethoxyethoxyethanol acrylic acid polymer ester as a monofunctional acrylic acid ester, 16.6 parts of an α -acryl- ω - (3, 6-dioxaoctane-1-yloxy) poly (oxyethylene carbonyl) (cas.no. 188746-52-3), 16.6 parts of a hexanediol ethylene oxide modified diacrylate Miramer 202 (manufactured by MIWON corporation) as a 2 functional acrylic acid ester, 16.6 parts of a tripropylene glycol diacrylate Miramer 220 (manufactured by MIWON corporation) as a 2 functional acrylic acid ester, 16.6 parts of a trimethylolpropane ethylene oxide modified triacrylate (manufactured by MIWON corporation) as a 3 functional acrylic acid ester, M3130 (manufactured by MIWON corporation) as a 20.8 parts, 1-hydroxy-cyclohexyl-phenyl-ketone "omni 184" manufactured by BASF corporation, 8.3 parts of nipil E170 (average particle size: 3 μm, manufactured by Tosoh Silica corporation), 5 parts of Minex 8F (manufactured by waex corporation) as a sodium aluminum silicate, 5 parts of polypropylene, and 3.501 parts of a polypropylene wax filler (manufactured by lubrk corporation) as a 3-particle size, and 3 parts of a radiation curable agent, and 1.501 parts of a stirrer, when mixed, and the mixture was applied thereto, and the mixture was subjected to a stirring.
(preparation of active energy ray-curable coating agent)
[ examples 2 to 19, comparative examples 1 to 11 ]
According to the compounding shown in tables 1 to 3, the same procedure as in example 1 was used to prepare each active energy ray-curable coating agent.
As the (meth) acryl-containing acrylic resin, 3 types of acrylic acrylate resin A (double bond equivalent of 250g/mol, weight average molecular weight of 25000, tg56 ℃, hydroxyl value of 113 mgKOH/g), acrylic acrylate resin B (double bond equivalent of 360g/mol, weight average molecular weight of 25000, tg73 ℃, hydroxyl value of 78 mgKOH/g), and acrylic acrylate resin C (double bond equivalent of 550g/mol, weight average molecular weight of 25000, tg85, hydroxyl value of 50 mgKOH/g) were used.
Further, as dipentaerythritol pentaacrylate mixture (DPHA), miramer M600 (manufactured by MIWON corporation) was used.
To examples 16 and 17, 1.2 parts of TEGORAD2700 (acrylic-modified polysiloxane Cas No. 157811-87-5, manufactured by Evonik Japan Co., ltd.) was added as a mold release agent.
In example 18, 20 parts of acrylic beads GM-0801 (average particle size 8 μm, manufactured by Aica industries Co., ltd.) were added for the purpose of further improving scratch resistance.
Production of decorative sheet
The active energy ray-curable coating agents prepared in examples 1 to 17 and comparative examples 1 to 11 were each applied using a bar coater (4 μm) using a black solid printing paper (thickness: 40 μm) as a base material, and then the coating film was cured by irradiation with ultraviolet light 1 time using a high-pressure mercury lamp. The building material paint was cured by placing the coating on a conveyor using a UV irradiation device (GS Yuasa Corporation) equipped with an air-cooled high-pressure mercury lamp (120W/cm 1 lamp output) and a belt conveyor, and passing under the lamp (irradiation distance 11 cm) at a speed of 25 m/min.
Ultraviolet irradiation amount is ultravioletThe cumulative light meter (Industrial UV Checker UVR-N1 manufactured by Kagaku Co., ltd., GS Yuasa Corporation) was confirmed to be 40mJ/cm 2 。
[ evaluation method ]
The evaluation method of the active energy ray-curable coating agent of the present invention is shown.
[ evaluation item 1: low gloss
The gloss (luster) value of each of the produced ultraviolet-cured decorative sheet surfaces was measured by using a japanese electrochromic gloss meter VG2000, and evaluated in the following 3 stages.
The measurement conditions of gloss were set to an incident angle of 60 ° and a reflection angle of 60 °.
(evaluation criterion)
O: the 60 degree gloss value is less than 15.
Delta: the glossiness value of 60 degrees is 15 or more and less than 30.
X: the 60-degree gloss value is 30 or more.
[ evaluation item 2: printing adaptability
After the coating was applied to the paper substrate, the state of the coating film after about 10 seconds was evaluated by visual observation in the following 4 steps.
(evaluation criterion)
And (3) the following materials: uniformly penetrated, and no coating unevenness was observed at all.
O: coating irregularities were slightly observed.
Delta: uneven coating was observed, but at a usable level.
X: the penetration into the paper substrate is rapid, and coating unevenness is remarkable.
[ evaluation item 3: cellotap (registered trademark) resistance ]
It is assumed that temporary fixation by means of an adhesive tape for a notice such as a memo or for alignment when a decorative sheet is actually processed at a construction site, a transparent adhesive tape is attached to a coating agent cured film on the surface of a decorative sheet using a black solid paper as a base material, and the transparent adhesive tape is rapidly peeled off, and this behavior is performed 10 times, and the state of the appearance of the printed film is evaluated in the following 3 stages.
(evaluation criterion)
O: no peeling of the printed coating was observed at all.
Delta: the printing film is 70% or more of the area ratio of the printing film is remained on the black solid paper
X: less than 70% of the printed coating remains on the black solid paper in terms of area ratio.
[ evaluation item 4: scratch resistance
The scratch resistance of the surface of the decorative sheet was evaluated visually in the following 3 stages by rubbing the surface of the coating film with a nail.
O: no change was observed at all.
Delta: with a shallow, light flaw in the tested part.
X: there were significantly deeper lesions in the tested part.
The evaluation results of the decorative sheet using each active energy ray-curable coating agent are shown in tables 1 to 3.
All values in the table are parts by mass or% by mass. Blank indicates unmated.
[ Table 1 ]
[ Table 2 ]
[ Table 3 ]
[ Table 4 ]
[ Table 5 ]
The decorative sheet using the active energy ray-curable coating agent of the present invention has both low gloss in matte style, excellent printing suitability without coating unevenness, and cellotap (registered trademark) resistance even without using an organic solvent.
In addition, if acrylic beads are added, scratch resistance of the decorative sheet surface is further improved.
Claims (6)
1. An active energy ray-curable coating agent characterized by comprising, as a curing component: a monofunctional (meth) acrylate monomer, a urethane (meth) acrylate which is a compound having a plurality of (meth) acryloyl groups, which is a reaction product of dicyclohexylmethane 4,4' -diisocyanate and a hydroxyl group-containing (meth) acrylate, and/or a (meth) acryloyl group-containing acrylic resin having a double bond equivalent weight of 100g/mol to 1000g/mol,
(1) The monofunctional (meth) acrylate monomer is 10 to 60 mass% of the total amount of the curing component,
(2) The urethane (meth) acrylate which is the reaction product of dicyclohexylmethane 4,4' -diisocyanate and the hydroxyl group-containing (meth) acrylate is 4 to 30% by mass based on the total amount of the curing component,
(3) The (meth) acryloyl group-containing acrylic resin having a double bond equivalent of 100g/mol to 1000g/mol is 0.1 to 20% by mass of the total amount of the curing component;
the (meth) acryloyl group-containing acrylic resin has a glass transition temperature Tg in the range of 40 to 130 ℃ and a hydroxyl value of 5 to 300mgKOH/g.
2. The active energy ray-curable coating agent according to claim 1, wherein the number average molecular weight of the monofunctional (meth) acrylate monomer is in the range of 100 to 1000.
3. The active energy ray-curable coating agent according to claim 1 or 2, further comprising a (meth) acrylate monomer having 2 or more functions.
4. The active energy ray-curable coating agent according to claim 1 or 2, further comprising a silicone epoxy (meth) acrylate.
5. The active energy ray-curable coating agent according to claim 1 or 2, which is free of a volatile organic solvent having a boiling point of less than 260 ℃ under normal pressure.
6. A coated building material comprising a coating film formed from the active energy ray-curable coating agent according to any one of claims 1 to 5.
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