CN113661064B - Active energy ray-curable resin composition, cured product, laminate, and article - Google Patents
Active energy ray-curable resin composition, cured product, laminate, and article Download PDFInfo
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- CN113661064B CN113661064B CN202080027289.XA CN202080027289A CN113661064B CN 113661064 B CN113661064 B CN 113661064B CN 202080027289 A CN202080027289 A CN 202080027289A CN 113661064 B CN113661064 B CN 113661064B
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- Prior art keywords
- meth
- acrylate
- active energy
- energy ray
- curable resin
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- 239000011342 resin composition Substances 0.000 title claims abstract description 66
- -1 acrylate compound Chemical class 0.000 claims abstract description 144
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 59
- 239000000758 substrate Substances 0.000 claims abstract description 40
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 176
- 239000011248 coating agent Substances 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 28
- 238000000576 coating method Methods 0.000 claims description 25
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 14
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 description 41
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 8
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- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 6
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 6
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
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- 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 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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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 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007647 flexography Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- NPEWZDADCAZMNF-UHFFFAOYSA-N gold iron Chemical compound [Fe].[Au] NPEWZDADCAZMNF-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000007760 metering rod coating Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 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
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical class FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 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
- 125000002347 octyl 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])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005076 polymer ester Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical compound [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- 239000008096 xylene Substances 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- 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
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Laminated Bodies (AREA)
Abstract
The present invention provides an active energy ray-curable resin composition comprising a urethane (meth) acrylate resin (A), a (meth) acrylate compound (B) having 1 or more and 2 or less (meth) acryloyl groups in one molecule, and a (meth) acrylate compound (C) having 3 or more (meth) acryloyl groups in one molecule; the weight average molecular weight of the urethane (meth) acrylate resin (a) is in the range of 1500 to 30000, and the content of the (meth) acrylate compound (B) is in the range of 10 to 50 mass% based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C). The active energy ray-curable resin composition can form a cured product excellent in hardness, scratch resistance and adhesion to a substrate.
Description
Technical Field
The present invention relates to an active energy ray-curable resin composition having excellent hardness, scratch resistance and adhesion to a substrate of a cured product, and a cured product, a laminate and an article each of which is formed from the active energy ray-curable resin composition.
Background
Resin materials having a (meth) acryloyl group are widely used in the fields of paints, coating agents, and the like, because they can be cured easily and instantaneously by ultraviolet irradiation and the like, and the cured products are excellent in transparency, hardness, and the like. Various kinds of objects to be coated, including optical films, plastic molded articles, wooden articles, etc., have been proposed, and various kinds of resins have been proposed according to the purpose, because of various properties required depending on the kind, application, etc. of the objects to be coated.
As a resin material having a (meth) acryloyl group, there is known: an active energy ray-curable resin composition containing a (meth) acryl-containing acrylic resin, pentaerythritol tetraacrylate, and pentaerythritol triacrylate (see, for example, patent document 1). The active energy ray-curable resin composition described in patent document 1 is useful as a coating agent for coating a thin plastic film, because the surface hardness of a cured product is excellent in balance with low cure shrinkage. However, there are the following problems: adhesion to a film substrate, particularly adhesion after long-term storage under high-temperature and humidity conditions, is low, and peeling is likely to occur. Further, it is known that an acrylic substrate is generally a substrate (hardly adhesive substrate) having insufficient adhesion to a coating agent, but the evaluation using an acrylic film is not performed in patent document 1, and the adhesion does not actually reach a practical level.
Acrylic films are widely used in display members, automotive members, and building materials. For example, a polarizing plate as one of display members is formed of a laminated film in which a polarizing element is sandwiched by transparent reinforcing films, and a triacetyl cellulose film has been conventionally used as a reinforcing film. In addition, in the automobile members which are made lightweight, an acrylic film is used as a top film for interior and exterior applications in response to the transition from metal to resin. Further, various applications using transparency and gloss such as plating substitution and coating substitution are mentioned.
As a hard coating agent for an acrylic film, for example, an active energy ray-curable composition containing tetrahydrofurfuryl acrylate, stearyl methacrylate, and an acrylic resin is known, but the adhesion to an acrylic film does not meet the market demand level (for example, see patent document 2).
Therefore, a material having excellent adhesion to a difficult-to-adhere substrate such as an acrylic substrate and excellent hardness and scratch resistance that can be used as a coating agent is demanded.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open publication No. 2011-207947
Patent document 2: japanese patent laid-open publication No. 2013-036024
Disclosure of Invention
Problems to be solved by the invention
The invention aims to solve the problems of providing: the cured product has excellent hardness, scratch resistance and substrate adhesion, and is formed into a cured product, a laminate and an article.
Solution for solving the problem
The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by using an active energy ray-curable resin composition containing a urethane (meth) acrylate resin having a specific weight average molecular weight, a specific amount of a (meth) acrylate compound having 1 or more and 2 or less (meth) acryloyl groups in one molecule, and a (meth) acrylate compound having 3 or more (meth) acryloyl groups in one molecule, and have completed the present invention.
Specifically, the present invention relates to an active energy ray-curable resin composition, which is characterized by containing a urethane (meth) acrylate resin (a), a (meth) acrylate compound (B) having 1 or more and 2 or less (meth) acryloyl groups in one molecule, and a (meth) acrylate compound (C) having 3 or more (meth) acryloyl groups in one molecule, wherein the weight average molecular weight of the urethane (meth) acrylate resin (a) is in the range of 1500 to 30000, and the content of the (meth) acrylate compound (B) is in the range of 10 to 50 mass% based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C), and a cured product, a laminate and an article formed from the active energy ray-curable resin composition.
ADVANTAGEOUS EFFECTS OF INVENTION
The active energy ray-curable resin composition of the present invention is excellent in hardness, scratch resistance and adhesion to a substrate, and therefore can be used as a coating agent or an adhesive, and in particular, can be suitably used as a coating agent.
Detailed Description
The active energy ray-curable resin composition of the present invention is characterized by comprising a urethane (meth) acrylate resin (A), a (meth) acrylate compound (B) having 1 or more and 2 or less (meth) acryloyl groups in one molecule, and a (meth) acrylate compound (C) having 3 or more (meth) acryloyl groups in one molecule.
In the present invention, "(meth) acrylate" means acrylate and/or methacrylate. In addition, "(meth) acryl" means acryl and/or methacryl. Further, "(meth) acrylic" means acrylic acid and/or methacrylic acid.
Examples of the urethane (meth) acrylate resin (a) include various polyisocyanate compounds, hydroxyl group-containing (meth) acrylate compounds, and, if necessary, those obtained by reacting various polyol compounds.
Examples of the polyisocyanate compound include aliphatic polyisocyanate compounds such as butane diisocyanate, hexamethylene diisocyanate, 2, 4-trimethylhexamethylene diisocyanate, and 2, 4-trimethylhexamethylene diisocyanate; alicyclic polyisocyanate compounds such as norbornane diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, and hydrogenated diphenylmethane diisocyanate; aromatic polyisocyanate compounds such as toluene diisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, diphenylmethane diisocyanate, 1, 5-naphthalene diisocyanate, 4 '-diisocyanato-3, 3' -dimethylbiphenyl and o-triazine diisocyanate; polymethylene polyphenyl polyisocyanates having a repeating structure represented by the following structural formula (1); isocyanurate modified products, biuret modified products, allophanate modified products, and the like. These polyisocyanate compounds may be used alone or in combination of 2 or more.
[ in formula (1), R 1 Each independently represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. R is R 2 Each independently represents an alkyl group having 1 to 4 carbon atoms or a bonding point connected to a structural part represented by the structural formula (1) via a methylene group having a sign. l is 0 or an integer of 1 to 3, and m is an integer of 1 to 15. ]
The hydroxyl group-containing (meth) acrylate compound is not particularly limited as long as it has a hydroxyl group and a (meth) acryloyl group in the molecular structure, and various compounds can be used. Examples thereof include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, di (trimethylolpropane) di (meth) acrylate, and di (trimethylolpropane) tri (meth) acrylate. Further, (poly) oxyalkylene modified products in which a (poly) oxyalkylene chain such as a (poly) oxyethylene chain, a (poly) oxypropylene chain, a (poly) oxytetramethylene chain or the like is introduced into the molecular structure of the various hydroxyl group-containing (meth) acrylate compounds may be used; a lactone modified product having a (poly) lactone structure is introduced into the molecular structure of the above-mentioned various hydroxyl group-containing (meth) acrylate compounds. These hydroxyl group-containing (meth) acrylate compounds may be used alone or in combination of 2 or more.
Examples of the polyol compound include aliphatic polyol compounds such as ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, glycerol, trimethylolpropane, di (trimethylolpropane), pentaerythritol, and dipentaerythritol; aromatic polyhydric alcohol compounds such as biphenol and bisphenol; (poly) oxyalkylene modified products having (poly) oxyalkylene chains such as (poly) oxyethylene chains, (poly) oxypropylene chains and (poly) oxytetramethylene chains introduced into the molecular structures of the various polyol compounds; a lactone modified body having a (poly) lactone structure and the like are introduced into the molecular structures of the various polyol compounds. These polyol compounds may be used alone or in combination of 2 or more.
The weight average molecular weight (Mw) of the urethane (meth) acrylate resin (a) is in the range of 1500 to 30000, and is preferably in the range of 2500 to 10000 in terms of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion. In the present invention, the weight average molecular weight (Mw) is a value measured by Gel Permeation Chromatography (GPC).
The (meth) acryl equivalent of the urethane (meth) acrylate resin (a) is preferably in the range of 90 to 500 g/equivalent, more preferably in the range of 90 to 250 g/equivalent, from the viewpoint of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion. In the present invention, the (meth) acryl equivalent of the urethane (meth) acrylate resin (a) is a value calculated as a theoretical value based on the reaction raw material.
In addition, from the viewpoint of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion, the content of the urethane (meth) acrylate resin (a) is preferably in the range of 20 to 80 mass%, more preferably in the range of 20 to 60 mass%, based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C).
As the (meth) acrylate compound (B), a compound having 1 or more and 2 or less (meth) acryloyl groups in one molecule is used.
Examples of the (meth) acrylic acid ester compound (B) include phenoxyethyl (meth) acrylate, phenoxybenzyl (meth) acrylate, cyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, cyclohexylmethyl (meth) acrylate, cyclohexylethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dipropylene glycol mono (meth) acrylate, isobornyl (meth) acrylate, norbornyl (meth) acrylate, isononyl (meth) acrylate, benzyl (meth) acrylate, phenylbenzyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, 2- (meth) acryloyloxyethyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylmethoxy (meth) acrylate, 2-ethoxy (meth) acrylate, 2-butoxy (meth) acrylate, 2-ethoxy (meth) acrylate, N-decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, butoxydiglycol (meth) acrylate, butoxytriethylene glycol (meth) acrylate, methoxydiglycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, trimethylolpropane (meth) acrylate, di (trimethylol propane) (meth) acrylate, pentaerythritol (meth) acrylate, dipentaerythritol (meth) acrylate, acryloylmorpholine, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, glycidyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanoethyl (meth) acrylate, dicyclopentanyloxypenta (meth) acrylate, penta (meth) acrylate, monofunctional (meth) acrylates such as tetramethylpiperidine (meth) acrylate, (2-methyl-2-ethyl-1, 3-dioxolan-4-yl) methyl (meth) acrylate, 3, 4-epoxycyclohexylmethyl methacrylate, cyclic trimethylolpropane methylal (meth) acrylate, 1-adamantyl (meth) acrylate, 2-adamantyl (meth) acrylate, and 2-methyl-2-adamantyl (meth) acrylate;
1, 6-hexanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified 1, 6-hexanediol di (meth) acrylate, hydroxypivalate neopentyl glycol di (meth) acrylate, propylene oxide modified neopentyl glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, ethylene oxide modified di (meth) acrylate of bisphenol A, propylene oxide modified di (meth) acrylate of bisphenol A, ethylene oxide modified di (meth) acrylate of bisphenol F, tricyclodecanedimethanol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, propylene oxide modified tri (meth) acrylate of glycerol, 2-hydroxy-3-acryloxypropylene oxide propyl (meth) acrylate, bisphenol A, ethylene oxide modified fluorenyl di (meth) acrylate, tetraethoxysilane (meth) acrylate, and the like, 2-functional (meth) acrylates such as phenoxyethylene glycol (meth) acrylate, stearyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinate, trifluoroethyl (meth) acrylate, 3-methyl-1, 5-pentanediol di (meth) acrylate, 2,3- [ (meth) acryloyloxymethyl ] norbornane, 2,5- [ (meth) acryloyloxymethyl ] norbornane, 2,6- [ (meth) acryloyloxymethyl ] norbornane, 1, 3-adamantyldi (meth) acrylate, 1, 3-bis [ (meth) acryloyloxymethyl ] adamantane, tris (hydroxyethyl) isocyanurate di (meth) acrylate, 3, 9-bis [1, 1-dimethyl-2- (meth) acryloyloxyethyl ] -2,4,8, 10-tetraoxaspiro [5.5] undecane, trimethylolpropane di (meth) acrylate, dipentaerythritol di (meth) acrylate, and di (trimethylolpropane) di (meth) acrylate.
Among them, the (meth) acrylate compound (b 1) having an alkylene oxide chain is preferable from the viewpoint of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion.
The (meth) acrylate compound (b 1) preferably has an alkylene oxide chain having 2 to 4 carbon atoms, and the average number of repetitions of the alkylene oxide chain in one molecule is preferably 4 or less.
The (meth) acrylate compound (b 1) may be, for example, a compound represented by the following structural formula (2).
[ in formula (2), R 1 Is a hydrogen atom or methyl group, R 2 Is any one of a hydrogen atom, a hydrocarbon group having 1 to 12 carbon atoms, (meth) acryl, phenyl, phenylphenol, t-butyl, methylphenyl, dicyclopentanyl, and dicyclopentanyl, n is an integer of 2 to 4, and m is an integer of 1 to 4.]
Among the (meth) acrylate compounds (b 1), hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and hydroxybutyl (meth) acrylate are more preferable from the viewpoint of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance, and substrate adhesion.
These (meth) acrylate compounds having 1 or more and 2 or less (meth) acryloyl groups in one molecule may be used alone or in combination of 2 or more.
In view of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion, the content of the (meth) acrylate compound (B) is in the range of 10 to 50 mass%, preferably in the range of 10 to 35 mass%, based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C).
As the (meth) acrylate compound (C), one having 3 or more (meth) acryloyl groups in one molecule is used. In view of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion, it is preferable to have 3 or more and 10 or less (meth) acryloyl groups in one molecule, and more preferable to have 3 or more and 6 or less.
Examples of the (meth) acrylate compound (C) include 3-functional (meth) acrylates such as EO-modified glycerol (meth) acrylate, PO-modified glycerol (meth) acrylate, pentaerythritol tri (meth) acrylate, EO-modified phosphotri (meth) acrylate, trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, HPA-modified trimethylolpropane tri (meth) acrylate, (EO) or (PO) -modified trimethylolpropane tri (meth) acrylate, alkyl-modified dipentaerythritol tri (meth) acrylate, tris (acryloxyethyl) isocyanurate, and tris (methacryloxyethyl) isocyanurate;
4-functional (meth) acrylates such as di (trimethylolpropane) tetra (meth) acrylate, pentaerythritol ethoxy tetra (meth) acrylate, and pentaerythritol tetra (meth) acrylate;
5-functional (meth) acrylates such as dipentaerythritol hydroxy penta (meth) acrylate and alkyl-modified dipentaerythritol penta (meth) acrylate;
dipentaerythritol hexa (meth) acrylate and the like 6-functional (meth) acrylate.
These (meth) acrylate compounds having 3 or more (meth) acryloyl groups in one molecule may be used alone or in combination of 2 or more. Among them, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate are preferable from the viewpoint of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion.
In view of obtaining an active energy ray-curable resin composition capable of forming a cured product having excellent hardness, scratch resistance and substrate adhesion, the content of the (meth) acrylate compound (C) is preferably in the range of 5 to 50 mass%, more preferably in the range of 10 to 35 mass%, based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C).
The active energy ray-curable resin composition of the present invention may contain the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C) as essential components, and may contain other active energy ray-curable resin components in combination within a range that does not impair the effects of the present invention.
The other active energy ray-curable resin component includes other (meth) acrylate resins (D) than the urethane (meth) acrylate resin (a). Examples of the other (meth) acrylate resin (D) include a dendritic (meth) acrylate resin (D1), an acrylic (meth) acrylate resin (D2), and an epoxy (meth) acrylate resin (D3). These other (meth) acrylate resins (D) may be used alone or in combination of 2 or more.
The branched (meth) acrylate resin (D1) is a resin having a regular multi-branched structure and having a (meth) acryloyl group at the end of each branched chain, and is also called a hyperbranched polymer, a star polymer, or the like, in addition to the branched type. Examples of such a compound include compounds represented by the following structural formulae (3-1) to (3-8), but are not limited to these, and any resin may be used as long as it has a regular multi-branched structure and has a (meth) acryloyl group at the end of each branch.
[ in the formulae (3-1) to (3-8), R 1 Is a hydrogen atom or methyl group, R 2 Is a hydrocarbon group having 1 to 4 carbon atoms.]
As such a branched (meth) acrylate resin (D1), there may be used "Biscoat#1000" manufactured by Osaka organic chemical Co., ltd., "weight average molecular weight (Mw) 1500-2000," average (meth) acryl number per molecule 14], "Biscoat 1020" [ weight average molecular weight (Mw) 1000-3000 ], "SIRIUS501" [ weight average molecular weight (Mw) 15000-23000 ], "SP-1106" manufactured by MIWON company [ weight average molecular weight (Mw) 1630, "average (meth) acryl number per molecule 18]," CN2301 "manufactured by SARTOMER company", "CN2302" [ average (meth) acryl number per molecule 16], "CN2303" [ average (meth) acryl number per molecule 6], "CN2304" [ average (meth) acryl number per molecule 18], new iron gold chemical Co., ltd., "ESDRIMER HU-22", new village chemical Co., ltd., "A-5-R" manufactured by SARTOMER company "manufacturing method" and "Japanese chemical Co., ltd.," HBR HYPER TECH ".
The weight average molecular weight (Mw) of the branched (meth) acrylate resin (D1) is preferably in the range of 1000 to 30000. The average number of (meth) acryloyl groups per molecule is preferably in the range of 5 to 30.
Examples of the acrylic (meth) acrylate resin (D2) include those obtained as follows: an acrylic resin intermediate is obtained by polymerizing a (meth) acrylate compound (α) having a reactive functional group such as a hydroxyl group, a carboxyl group, an isocyanate group, or a glycidyl group as an essential component, and by further reacting the acrylic resin intermediate with a (meth) acrylate compound (β) having a reactive functional group capable of reacting with these functional groups, a (meth) acryloyl group is introduced.
Examples of the (meth) acrylate compound (α) having the reactive functional group include hydroxyl group-containing (meth) acrylate monomers such as hydroxyethyl (meth) acrylate and hydroxypropyl (meth) acrylate; carboxyl group-containing (meth) acrylate monomers such as (meth) acrylic acid; isocyanate group-containing (meth) acrylate monomers such as 2-acryloyloxyethyl isocyanate, 2-methacryloyloxyethyl isocyanate and 1, 1-bis (acryloyloxymethyl) ethyl isocyanate; glycidyl (meth) acrylate monomers such as glycidyl (meth) acrylate and 4-hydroxybutyl acrylate glycidyl ether. These may be used alone or in combination of 2 or more.
In the acrylic resin intermediate, other polymerizable unsaturated group-containing compounds may be copolymerized in addition to the (meth) acrylate compound (α) as required. Examples of the other polymerizable unsaturated group-containing compound include alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate; alicyclic structure-containing (meth) acrylates such as cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentanyl (meth) acrylate; aromatic ring-containing (meth) acrylates such as phenyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl acrylate, and the like; silyl (meth) acrylate such as 3-methacryloxypropyl trimethoxysilane; styrene derivatives such as styrene, α -methylstyrene and chlorostyrene. These may be used alone or in combination of 2 or more.
The acrylic resin intermediate can be produced by the same method as that for a usual acrylic resin. As an example of the production conditions, for example, various monomers can be polymerized in the presence of a polymerization initiator at a temperature range of 60 to 150 ℃. Examples of the polymerization method include bulk polymerization, solution polymerization, suspension polymerization, and emulsion polymerization. Examples of the polymerization pattern include random copolymers, block copolymers, and graft copolymers. When the polymerization is carried out by the solution polymerization method, for example, ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone, glycol ether solvents such as propylene glycol monomethyl ether, propylene glycol dimethyl ether, propylene glycol monopropyl ether and propylene glycol monobutyl ether can be preferably used.
The (meth) acrylate compound (β) may be reacted with a reactive functional group of the (meth) acrylate compound (α), and the following combination is preferable from the viewpoint of reactivity. That is, when a hydroxyl group-containing (meth) acrylate is used as the (meth) acrylate compound (α), an isocyanate group-containing (meth) acrylate is preferably used as the (meth) acrylate compound (β). When a carboxyl group-containing (meth) acrylate is used as the (meth) acrylate compound (α), a glycidyl group-containing (meth) acrylate is preferably used as the (meth) acrylate compound (β). When an isocyanate group-containing (meth) acrylate is used as the (meth) acrylate compound (. Alpha.), a hydroxyl group-containing (meth) acrylate is preferably used as the (meth) acrylate compound (. Beta.). When a glycidyl group-containing (meth) acrylate is used as the (meth) acrylate compound (α), a carboxyl group-containing (meth) acrylate is preferably used as the (meth) acrylate compound (β). The (meth) acrylate compound (. Beta.) may be used alone or in combination of 2 or more.
In the reaction of the acrylic resin intermediate and the (meth) acrylate compound (. Beta.) described above, for example, when the reaction is an esterification reaction, there is a method in which an esterification catalyst such as triphenylphosphine is suitably used at a temperature in the range of 60 to 150 ℃. When the reaction is a urethanization reaction, a method of reacting the acrylic resin intermediate by dropping the compound (. Beta.) at a temperature in the range of 50 to 120℃is exemplified. The (meth) acrylate compound (. Beta.) is preferably used in a range of 1.0 to 1.1 mol based on 1 mol of the functional group in the acrylic resin intermediate.
The epoxy (meth) acrylate resin (D3) may be obtained by, for example, reacting an epoxy resin with (meth) acrylic acid or an anhydride thereof. Examples of the epoxy resin include diglycidyl ethers of dihydric phenols such as hydroquinone and catechol; diglycidyl ethers of bisphenol compounds such as 3,3 '-biphenyldiol and 4,4' -biphenyldiol; bisphenol a type epoxy resins, bisphenol B type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, and other bisphenol type epoxy resins; polyglycidyl ethers of naphthol compounds such as 1, 4-naphthalene diol, 1, 5-naphthalene diol, 1, 6-naphthalene diol, 2, 7-naphthalene diol, binaphthol, and bis (2, 7-dihydroxynaphthyl) methane; triglycidyl ethers such as 4,4',4 "-methyltrisperidol; novolac type epoxy resins such as phenol novolac type epoxy resins and cresol novolac type epoxy resins; (poly) oxyalkylene modified products having (poly) oxyalkylene chains such as (poly) oxyethylene chains, (poly) oxypropylene chains and (poly) oxytetramethylene chains introduced into the molecular structures of the various epoxy resins; a lactone modified product having a (poly) lactone structure is introduced into the molecular structure of the various epoxy resins.
The active energy ray-curable resin composition of the present invention preferably uses a photopolymerization initiator depending on the type of active energy rays used. Examples of the photopolymerization initiator include α -hydroxyketone type, α -aminoketone type, bisacylphosphine oxide type, monoacylphosphine oxide type, hydrogen abstraction type, oxime ester type, aminobenzoate type, ketone sulfone type, bisimidazole type, phenyl ether type, and phenylketal type. Specifically, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- [ 4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propane-1-one, thioxanthone derivatives, 2' -dimethoxy-1, 2-diphenylethane-1-one, diphenyl (2, 4, 6-trimethoxybenzoyl) phosphine oxide, 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide, bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, and the like can be exemplified.
As the other photopolymerization initiator, commercially available products, examples thereof include "Omnirad-1173", "Omnirad-184", "Omnirad-127", "Omnirad-2959", "Omnirad-369", "Omnirad-379", "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", "Omnirad-754", "Omnirad-784", "Omnirad-500", "Omnirad-81" (manufactured by IGM corporation), "Kayacure-DETX", "Kayacure-DMBI", "Kayacure-EPA", "Kayacure-OA" (manufactured by Japanese chemical Co., ltd., "Vicure-10", "Vicure-55" (manufactured by Stouffer Chemical Cmopany) "," Trigonal P1 "(manufactured by Akzo Co., sanrun-1000", "Sanrun-Z", "manufactured by IK-UK) (manufactured by IK-UK) and the company" IK-UK "(manufactured by IK-UK) and the UK-UK). These photopolymerization initiators may be used alone or in combination of 2 or more. The photopolymerization initiator may be used in combination with a photosensitizer such as an amine compound, a urea compound, a sulfur-containing compound, a phosphorus-containing compound, a chlorine-containing compound, and a nitrile compound.
The amount of the photopolymerization initiator used is preferably in the range of 0.05 to 20 parts by mass, more preferably in the range of 0.1 to 10 parts by mass, per 100 parts by mass of the components other than the organic solvent in the active energy ray-curable composition of the present invention.
The active energy ray-curable resin composition used in the present invention may further contain other components. Examples of the other components include inorganic fine particles, silane coupling agents, phosphate compounds, solvents, ultraviolet absorbers, antioxidants, silicon-based additives, fluorine-based additives, antistatic agents, organic microbeads, quantum Dots (QDs), rheology control agents, antifoaming agents, antifogging agents, colorants, and the like.
The inorganic fine particles are added for the purpose of adjusting the hardness, refractive index, etc. of the cured coating film of the active energy ray-curable resin composition, and various known and conventionally used inorganic fine particles can be used. Examples of the fine particles include silica, alumina, zirconia, titania, barium titanate, and antimony trioxide. These may be used alone or in combination of two or more. Among silica particles having particularly high versatility, various types of wet silica, called fumed silica, precipitated silica, gel silica, sol gel silica, and the like, can be used. The surface of the inorganic fine particles may be modified with a silane coupling agent or the like. The particle diameter of the inorganic fine particles is appropriately adjusted according to the desired coating properties and the like, and the measurement value by the dynamic light scattering method is preferably in the range of 10 to 250 nm. When the inorganic fine particles are used, the amount of the inorganic fine particles to be added is preferably in the range of 0.1 to 60 mass% based on the total amount of the components other than the solvent of the curable composition.
Examples of the silane coupling agent include (meth) acryloyloxy silane coupling agents such as [ (meth) acryloyloxyalkyl ] trialkylsilane, [ (meth) acryloyloxyalkyl ] dialkylalkoxysilane, [ (meth) acryloyloxyalkyl ] alkyldialkoxysilane, [ (meth) acryloyloxyalkyl ] trialkoxysilane; vinyl silane coupling agents such as trialkylvinyl silane, dialkylalkoxysilane, alkyldialkoxyvinyl silane, trialkoxyvinyl silane, trialkylallylsilane, dialkylalkoxyallylsilane, alkyldialkoxyallylsilane, trialkoxyallylsilane, and the like; styrene-based silane coupling agents such as styryltrialkyl, styryldialkylalkoxysilane, styrylalkyldialkoxysilane, and styryltrialkoxysilane; epoxy silane coupling agents such as (glycidoxyalkyl) trialkylsilane, (glycidoxyalkyl) dialkylalkoxysilane, (glycidoxyalkyl) alkyldialkoxysilane, (glycidoxyalkyl) trialkoxysilane, [ (3, 4-epoxycyclohexyl) alkyl ] trimethoxysilane, [ (3, 4-epoxycyclohexyl) alkyl ] trialkylsilane, [ (3, 4-epoxycyclohexyl) alkyl ] dialkylalkoxysilane, [ (3, 4-epoxycyclohexyl) alkyl ] alkyldialkoxysilane, [ (3, 4-epoxycyclohexyl) alkyl ] trialkoxysilane; isocyanate-based silane coupling agents such as (isocyanatoalkyl) trialkylsilane, (isocyanatoalkyl) dialkylalkoxysilane, (isocyanatoalkyl) alkyldialkoxysilane and (isocyanatoalkyl) trialkoxysilane. These may be used alone or in combination of 2 or more kinds.
Examples of the commercial products of the above-mentioned phosphate compounds include "KAYAMER PM-2" manufactured by Kagaku Kogyo Co., ltd., "KAYAMER PM-21", manufactured by Kagaku Kogyo Co., ltd., "Light ester P-1M", "Light ester P-1A (N)", manufactured by SOLVAY, manufactured "SIPOMER PAM 100" manufactured by SOLVAY, SIPOMER PAM 200"," SIPOMER PAM 300"," SIPOMER PAM 4000", manufactured by Osaka organic chemical industry Co., ltd.," Biscoat#3PA "manufactured by Biscoat#3PMA", manufactured by Kagaku Kogyo Co., ltd., "New front S-23A"; and "SIPOMER PAM 5000" manufactured by SOLVAY Co., ltd., which is a phosphate compound having an allyl ether group in its molecular structure.
The solvent is added for the purpose of adjusting the coating viscosity of the active energy ray-curable resin composition, and the kind and the amount of the solvent added are appropriately adjusted according to the desired properties. Generally, the active energy ray-curable resin composition is used such that the nonvolatile content thereof is in the range of 10 to 90 mass%. Specific examples of the solvent include ketone solvents such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; cyclic ether solvents such as tetrahydrofuran and dioxolane; esters such as methyl acetate, ethyl acetate, and butyl acetate; aromatic solvents such as toluene and xylene; alicyclic solvents such as cyclohexane and methylcyclohexane; alcohol solvents such as carbitol, cellosolve, methanol, isopropanol, butanol, propylene glycol monomethyl ether, and the like; glycol ether solvents such as ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monopropyl ether. These may be used alone or in combination of 2 or more.
Examples of the ultraviolet absorber include triazine derivatives such as 2- [4- { (2-hydroxy-3-dodecyloxypropyl) oxy } -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- [4- { (2-hydroxy-3-tridecyloxypropyl) oxy } -2-hydroxyphenyl ] -4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazine, 2- (2 '-xanthenecarboxy-5' -methylphenyl) benzotriazole, 2- (2 '-o-nitrobenzyloxy-5' -methylphenyl) benzotriazole, 2-xanthenecarboxy-4-dodecyloxybenzophenone, and 2-o-nitrobenzyloxy-4-dodecyloxybenzophenone. These may be used alone or in combination of 2 or more.
Examples of the antioxidant include hindered phenol antioxidants, hindered amine antioxidants, organic sulfur antioxidants, and phosphate antioxidants. These may be used alone or in combination of 2 or more.
Examples of the silicon-based additive include a polydimethylsiloxane having an alkyl group or a phenyl group, a polydimethylsiloxane having a polyether-modified acrylic group, and a polydimethylsiloxane having a polyester-modified acrylic group, such as a dimethylpolysiloxane, a methylphenyl polysiloxane, a cyclic dimethylpolysiloxane, a methyl hydrogen polysiloxane, a polyether-modified dimethylpolysiloxane copolymer, a polyester-modified dimethylpolysiloxane copolymer, a fluorine-modified dimethylpolysiloxane copolymer, and an amino-modified dimethylpolysiloxane copolymer. These may be used alone or in combination of 2 or more.
Examples of the fluorine-containing additive include the "MEGAFACE" series of DIC Co., ltd. These may be used alone or in combination of 2 or more.
Examples of the antistatic agent include pyridinium, imidazolium, phosphonium, ammonium, or lithium salts of bis (trifluoromethanesulfonyl) imide or bis (fluorosulfonyl) imide. These may be used alone or in combination of 2 or more.
Examples of the organic beads include polymethyl methacrylate beads, polycarbonate beads, polystyrene beads, polyacrylic styrene beads, silicone beads, glass beads, acrylic beads, benzoguanamine resin beads, melamine resin beads, polyolefin resin beads, polyester resin beads, polyamide resin beads, polyimide resin beads, polyvinylidene fluoride resin beads, and polyethylene resin beads. These may be used alone or in combination of 2 or more. The average particle diameter of these organic microbeads is preferably in the range of 1 to 10. Mu.m.
Examples of the Quantum Dot (QD) include a group II-V semiconductor compound, a group II-VI semiconductor compound, a group III-IV semiconductor compound, a group III-V semiconductor compound, a group III-VI semiconductor compound, a group IV-VI semiconductor compound, a group I-III-VI semiconductor compound, a group II-IV-V semiconductor compound, a group I-II-IV-VI semiconductor compound, a group IV element, and a compound containing these. Examples of the group II-VI semiconductor compound include binary compounds such as ZnO, znS, znSe, znTe, cdS, cdSe, cdTe, hgS, hgSe, hgTe; znSeS, znSeTe, znSTe, cdZnS, cdZnSe, cdZnTe, cdSeS, cdSeTe, cdSTe, cdHgS, cdHgSe, cdHgTe, hgSeS, hgSeTe, hgSTe, hgZnS, hgZnSe, hgZnTe, etc.; cdZnSeS, cdZnSeTe, cdZnSTe, cdHgSeS, cdHgSeTe, cdHgSTe, cdHgZnTe, hgZnSeS, hgZnSeTe, hgZnSTe, and the like. Examples of the group III-IV semiconductor compound include B 4 C 3 、Al 4 C 3 、Ga 4 C 3 Etc. Examples of the group III-V semiconductor compound include binary compounds such as BP, BN, alN, alP, alAs, alSb, gaN, gaP, gaAs, gaSb, inN, inP, inAs, inSb; gaNP, gaNAs, gaNSb, gaPAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inNP, inNAs, inNSb, inPAs, inPSb, gaAlNP, etc.; gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gaInNP, gaInNAs, gaInNSb, gaInPAs, gaInPSb, inAlNP, inAlNAs, inAlNSb, inAlPAs, inAlPSb, etc. Examples of the III-VI semiconductor compound include Al 2 S 3 、Al 2 Se 3 、Al 2 Te 3 、Ga 2 S 3 、Ga 2 Se 3 、Ga 2 Te 3 、GaTe、In 2 S 3 、In 2 Se 3 、In 2 Te 3 And InTe. Examples of the group IV-VI semiconductor compound include binary compounds such as SnS, snSe, snTe, pbS, pbSe, pbTe; snSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe, snPbTe, etc.; snPbSSe, snPbSeTe, snPbSTe, and the like. Examples of the group I-III-VI semiconductor compound include CuInS 2 、CuInSe 2 、CuInTe 2 、CuGaS 2 、CuGaSe 2 、CuGaSe 2 、AgInS 2 、AgInSe 2 、AgInTe 2 、AgGaSe 2 、AgGaS 2 、AgGaTe 2 Etc. Examples of the group IV element or the compound containing the same include C, si, ge, siC, siGe. The quantum dot may be formed of a single semiconductor compound or may have a core-shell structure formed of a plurality of semiconductor compounds. In addition, the surface thereof may be modified by an organic compound.
These various additives may be added in any amount depending on desired properties and the like, and are usually used in a range of 0.01 to 40 parts by mass in total of 100 parts by mass of components other than the solvent in the active energy ray-curable resin composition.
The active energy ray-curable resin composition used in the present invention is produced by mixing the above-described blend components. The mixing method is not particularly limited, and a paint stirrer, a disperser, a roll mill, a bead mill, a ball mill, an attritor, a sand mill, a bead mill, or the like may be used.
The cured product of the present invention can be obtained by irradiating the active energy ray-curable resin composition with active energy rays. Examples of the active energy rays include ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. In the case of using ultraviolet rays as the active energy rays, the ultraviolet ray-based curing reaction is efficiently performed, and the irradiation may be performed under an inert gas atmosphere such as nitrogen or under an air atmosphere.
Ultraviolet lamps are generally used as ultraviolet light generating sources from the viewpoints of practicality and economy. Specifically, a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a xenon lamp, a gallium lamp, a metal halide lamp, sunlight, an LED, and the like can be cited.
The cumulative amount of the active energy rays is not particularly limited, but is preferably 10 to 5000mJ/cm 2 More preferably 50 to 1000mJ/cm 2 . When the cumulative light amount is within the above range, the occurrence of uncured portions can be prevented or suppressed, which is preferable.
The irradiation with the active energy ray may be performed in one stage or in two or more stages.
The laminate of the present invention can be obtained by applying the active energy ray-curable resin composition onto a substrate and irradiating the substrate with active energy rays to cure the resin composition.
Examples of the substrate include various plastic substrates such as cellulose triacetate, polyester, acrylic, cycloolefin polymer, polyamide, polyimide, polystyrene, polycarbonate, and polypropylene. Among these, a laminate using a base material made of acrylic is particularly preferable because the laminate has particularly excellent adhesion to a cured coating film. The substrate may be in a film form.
The acrylic substrate is a substrate formed using a thermoplastic acrylic resin, and examples of the (meth) acrylic ester monomer constituting the thermoplastic acrylic resin include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, myristyl (meth) acrylate, palmityl (meth) acrylate, stearyl (meth) acrylate, behenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, and the like. These (meth) acrylate monomers may be used alone or in combination of 2 or more.
Further, the film-like acrylic base material may be a commercially available base material, and examples thereof include "ACRYLEN" manufactured by Mitsubishi chemical corporation, "PARAPURE" manufactured by Kagaku, "TECHNOLLOY" manufactured by Escarbo Sheet, and "SUNDUREN" manufactured by Sunduce Zhong Hua, and "Escarbo Sheet" manufactured by Sumitomo chemical corporation.
Examples of the method for forming the cured coating film include a coating method, a transfer method, and a sheet adhesion method.
The coating method is a method of spraying the coating material, or applying a surface coating layer to a molded article using a printing apparatus such as a curtain coater, roll coater, gravure coater, or the like, and then curing the surface coating layer by irradiation with active energy rays.
The transfer method is as follows: a method in which a transfer material obtained by applying the above-mentioned active energy ray-curable composition onto a releasable substrate sheet is adhered to the surface of a molded article, and then the substrate sheet is peeled off to transfer the topcoat layer onto the surface of the molded article, and then the surface is cured by irradiation with active energy rays; or a method in which the transfer material is adhered to the surface of a molded article, and then the surface coating layer is transferred to the surface of the molded article by peeling the base sheet after curing by irradiation with an active energy ray.
The sheet adhesion method is a method of adhering a protective sheet having a coating film formed of the curable composition on a base sheet or a protective sheet having a coating film formed of the curable composition and a decorative layer on a base sheet to a plastic molded article to form a protective layer on the surface of the molded article.
Specifically, the sheet bonding method includes the following methods: a method (post-bonding method) in which a base sheet of a protective layer forming sheet prepared in advance is bonded to a molded article, and then heat-cured by heating to crosslink and cure a resin layer which is B-staged; and a method (molding simultaneous bonding method) in which the protective layer forming sheet is sandwiched between molding dies, the cavity is filled with resin, the surface of the resin molded article is bonded to the protective layer forming sheet, and then the resin layer is crosslinked and cured by heating and thermally curing the resin layer.
When a film-like acrylic substrate is used as the substrate, the coating amount of the active energy ray-curable resin composition of the present invention when applied to the film-like acrylic substrate is preferably adjusted so that the film thickness after curing is in the range of 1 to 100. Mu.m. Examples of the coating method include bar coater coating, die coating, spray coating, curtain coating, meyer bar coating, air knife coating, gravure coating, reverse gravure coating, offset printing, flexography, and screen printing. When the active energy ray-curable resin composition of the present invention contains an organic solvent, it is preferable that the active energy ray-curable resin composition is cured by irradiation of an active energy ray after the organic solvent is volatilized by heating at 80 to 150 ℃ for several tens of seconds to several minutes after coating.
The laminate of the present invention may have a layer structure other than the cured coating film formed from the active energy ray-curable resin composition. The method for forming these various layer structures is not particularly limited, and may be, for example, a method in which a resin raw material is directly applied, or a method in which a layer formed into a sheet in advance is bonded by an adhesive.
The article of the present invention has the laminate on the surface. Examples of the article include plastic molded articles such as cellular phones, home electric appliances, automobile interior and exterior materials, OA equipment, and the like.
Examples
Hereinafter, the present invention will be specifically described with reference to examples and comparative examples.
In this example, the weight average molecular weight (Mw) was measured by Gel Permeation Chromatography (GPC) under the following conditions.
A measuring device; HLC-8220 manufactured by Tosoh Co., ltd
A column; protection column H manufactured by Tosoh Co., ltd XL -H
+TSKgel G5000HXL manufactured by Tosoh Co., ltd
+TSKgel G4000HXL manufactured by Tosoh Co., ltd
+TSKgel G3000HXL manufactured by Tosoh Co., ltd
+TSKgel G2000HXL manufactured by Tosoh Co., ltd
A detector; RI (differential refractometer)
And (3) data processing: SC-8010 manufactured by Tosoh Co., ltd
Measurement conditions: column temperature 40 DEG C
Solvent tetrahydrofuran
Flow rate 1.0 ml/min
A standard; polystyrene
A sample; a sample (100. Mu.l) obtained by filtering a tetrahydrofuran solution having a mass% of 0.4% calculated as a resin solid matter conversion was filtered with a microfilter
( Synthesis example 1: production of urethane (meth) acrylate resin (A-1) )
A four-necked flask was charged with 510 parts by mass of a mixture of pentaerythritol diacrylate, pentaerythritol triacrylate and pentaerythritol tetraacrylate (Aronix M-305, manufactured by Toyo Kagaku Co., ltd., hydroxyl value 110 mgKOH/g), 0.22 part by mass of dibutyltin dilaurate and 0.22 part by mass of hydroquinone to prepare a homogeneous solution. After heating to 50℃in the flask, 111 parts by mass of isophorone diisocyanate (Evonik Japan Co., ltd. "VESTANAT IPDI") was added in portions over about 1 hour. After allowing the reaction mixture to react at 80℃for 3 hours and confirming the disappearance of the isocyanate group by infrared absorption spectrum, the nonvolatile content was adjusted to 80% by using butyl acetate to obtain a urethane (meth) acrylate resin (A-1). The weight average molecular weight (Mw) of the urethane (meth) acrylate resin (A-1) was 1800, and the acryl equivalent calculated on the basis of the charged raw material was 115 g/equivalent.
( Synthesis examples 2 to 9: production of urethane (meth) acrylate resins (A-2) to (A-9) )
Urethane (meth) acrylate resins (a-2) to (a-9) were obtained in the same manner as in synthesis example 1 according to the compounding ratios shown in table 1.
TABLE 1
In Table 1, "M-305" represents a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate (Aronix M-305, manufactured by Toyama Synthesis Co., ltd.).
In Table 1, "M-306" represents a mixture of pentaerythritol diacrylate, pentaerythritol triacrylate and pentaerythritol tetraacrylate (Aronix M-306, manufactured by Toyo Kagaku Co., ltd.).
In Table 1, "M-403" represents a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (Aronix M-403, manufactured by Toyama Synthesis Co., ltd.).
In Table 1, "M-404" represents a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (Aronix M-404, manufactured by Toyama Synthesis Co., ltd.).
In Table 1, "HEA" means hydroxyethyl acrylate.
In Table 1, "IPDI" means isophorone diisocyanate.
In Table 1, "HDI" means hexamethylene diisocyanate.
In Table 1, "H6XDI" represents hydrogenated xylylene diisocyanate.
In Table 1, "HDI urethane" means the urethane body of hexamethylene diisocyanate.
In Table 1, "XDI" represents xylylene diisocyanate.
( Synthesis example 10: production of acrylic (meth) acrylate resin (A' -1) )
33.3 parts by mass of methyl isobutyl ketone was charged into a reaction apparatus equipped with a stirring device, a cooling tube, a dropping funnel and a nitrogen inlet tube, and the temperature in the system was heated to 110℃while stirring. Then, a mixed solution composed of 100 parts by mass of glycidyl methacrylate, 4 parts by mass of t-butyl peroxy-2-ethylhexanoate (PERBUTYL O, manufactured by Nitro Co., ltd.) and 36 parts by mass of methyl isobutyl ketone was added dropwise over 4 hours. After the dropping, stirring was continued at 110℃for 10 hours to obtain an acrylic resin intermediate (1) solution having a nonvolatile content of 60% by mass. The epoxy equivalent of the acrylic resin intermediate (1) was 148 g/equivalent.
Then, 173 parts by mass (in terms of resin solid content) of the acrylic resin intermediate (1), 51 parts by mass of acrylic acid, 0.08 part by mass of p-methoxyphenol (methoquinone), 0.8 part by mass of triphenylphosphine, and 87 parts by mass of methyl isobutyl ketone were charged into a reaction apparatus equipped with a stirring device, a cooling tube, a dropping funnel, and an air inlet tube. The reaction mixture was heated to 105℃with bubbling of air, and the reaction was carried out for 10 hours, whereby an acrylic (meth) acrylate resin (A' -1) solution having a nonvolatile content of 50.5% by mass was obtained. The (meth) acryl equivalent of the acrylic (meth) acrylate resin (a' -1) was 213 g/equivalent, the number average molecular weight (Mn) was 12000, and the weight average molecular weight (Mw) was 22000.
( Example 1: preparation of active energy ray-curable resin composition (1) and production of laminate (L1) )
50 parts by mass (calculated as solid content) of the urethane (meth) acrylate resin (A-1) having 80% by mass of the nonvolatile component obtained in Synthesis example 1, 35 parts by mass of polyethylene glycol monoacrylate (AE-90U, manufactured by Nippon Co., ltd.), 25 parts by mass of pentaerythritol tetraacrylate (Aronix M-450, manufactured by Toyama Co., ltd.), 8 parts by mass of a photopolymerization initiator (Omnirad-184, manufactured by IGM Co., ltd.) and 140 parts by mass of methyl ethyl ketone were mixed to obtain an active energy ray-curable resin composition (1).
Then, the obtained active energy ray-curable resin composition (1) was applied onto an acrylic film having a thickness of 40. Mu.m, and dried at 90℃for 1 minute. Then, 50mJ/cm was irradiated with a 80W high-pressure mercury lamp under a nitrogen atmosphere 2 Ultraviolet light, a laminate (L1) having a cured coating film having a film thickness of 5 μm on the acrylic film was obtained.
( Examples 2 to 25: preparation of active energy ray-curable resin compositions (2) to (25) and production of laminates (L2) to (L25) )
Active energy ray-curable resin compositions (2) to (25) were obtained in the same manner as in example 1 with the compositions and the compounding ratios shown in tables 2 and 3. Further, using the obtained active energy ray-curable resin composition, laminates (L2) to (L25) were obtained in the same manner as in example 1.
( Comparative example 1: preparation of active energy ray-curable resin compositions (C1) to (C5) and production of laminates (L26) to (L30) )
Active energy ray-curable resin compositions (C1) to (C5) were obtained in the same manner as in example 1 with the compositions and the compounding ratios shown in table 4. Using the obtained active energy ray-curable composition, laminates (L26) to (L30) were obtained in the same manner as in example 1.
The laminates (L1) to (L30) obtained in the examples and comparative examples were used to carry out the following evaluations.
[ evaluation method of Pencil hardness ]
The pencil hardness of the coating film surface of the laminate obtained in examples and comparative examples was measured under a load of 500g in accordance with JIS K5600-5-4 (1999). Each hardness was measured 5 times, and the hardness measured 4 times or more without scratches was regarded as the hardness of the cured coating film, and was evaluated according to the following criteria.
A: the pencil hardness is more than 2H.
B: the pencil hardness is H or more and less than 2H.
C: the pencil hardness is less than H.
[ method of evaluating scratch resistance ]
A disc-shaped indenter having a diameter of 2.4 cm was wrapped with 0.5g of steel wool (NIPPON STEEL WOOL co., ltd. "BONSTAR # 0000"), and a load of 500g was applied to the indenter, and the coated surface of the laminate obtained in examples and comparative examples was reciprocated 10 times, thereby performing an abrasion test. Haze values of the laminated films before and after the abrasion test were measured using Suga Test Instruments co., ltd. Entitled "Haze computer HZ-2", and the difference (dH) between them was used to evaluate the films according to the following criteria. The smaller the difference (dH), the higher the resistance to scratch.
A: dH is 1.0 or less
B: dH is more than 1.0 and less than 3.0.
C: dH is more than 3.0 to 5.0 or less.
D: dH is more than 5.0 to 10.
E: dH is greater than 10.
[ method for evaluating substrate adhesion (initial) ]
Cut cuts were made on the cured coating film surfaces of the laminates obtained in examples and comparative examples by a cutter, 100 1mm×1mm checkerboards were produced, and after the scotch tape was attached thereto, peeling operation was rapidly performed, and the number of the remaining checkerboards which were not peeled was counted and evaluated according to the following criteria.
A: the number of residues in the checkerboard is more than 80.
B: the number of residues in the checkerboard is 50 or more and less than 80.
C: the number of residues in the checkerboard is 30 or more and less than 50.
D: the number of residues in the checkerboard is less than 30.
[ method for evaluating substrate adhesion (after light resistance test) ]
The laminates obtained in examples and comparative examples were subjected to light irradiation for 50 hours using Suga Test Instruments co., ltd. Fading meter "U48AU" (63 ℃ c., humidity 50%). Thereafter, the adhesion (initiation) to the substrate was carried out by the same method as described above, and the evaluation was carried out according to the following criteria.
A: the number of residues in the checkerboard is more than 80.
B: the number of residues in the checkerboard is 50 or more and less than 80.
C: the number of residues in the checkerboard is 30 or more and less than 50.
D: the number of residues in the checkerboard is less than 30.
The compositions of the active energy ray-curable resin compositions (1) to (29) prepared in examples 1 to 29 and the evaluation results of the laminated bodies (L1) to (L29) prepared in examples 1 to 29 are shown in tables 2 and 3.
TABLE 2
TABLE 3
The compositions of the active energy ray-curable resin compositions (C1) to (C5) prepared in comparative examples 1 to 5 and the evaluation results of the laminates (L30) to (L34) prepared in comparative examples 1 to 5 are shown in table 4.
TABLE 4
In tables 2 to 4, "BLEMER AE-90U" represents polyethylene glycol monoacrylate (BLEMER AE-90U, manufactured by Nikki Co., ltd., average repetition number of alkylene oxide chain 2).
In tables 2 and 4, "HEA" represents hydroxyethyl acrylate.
In tables 2 and 3, "4HBA" represents 4-hydroxybutyl acrylate.
In tables 2 and 3, "Biscoat #190" represents ethyl carbitol acrylate (Biscoat #190 manufactured by osaka organic chemical industry co., ltd.).
In tables 2 and 3, "Biscoat #190D" represents ethoxyethoxyethanol acrylic acid polymer ester (Biscoat #190D manufactured by osaka organic chemical industry co., ltd.).
In tables 2 and 3, "Biscoat #260" represents 1, 9-nonanediol diacrylate (Biscoat #260 manufactured by Osaka organic chemical Co., ltd.).
In tables 2 to 4, "M-450" represents pentaerythritol tetraacrylate (Aronix M-450, manufactured by Toyo Kagaku Co., ltd.).
In Table 3, "M-404" represents a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate (Aronix M-404, manufactured by Toyama Synthesis Co., ltd.).
Examples 1 to 29 shown in tables 2 and 3 are examples of laminates using the active energy ray-curable resin composition of the present invention. The laminate was confirmed to have excellent coating hardness, scratch resistance and substrate adhesion.
On the other hand, comparative example 1 shown in table 4 is an example in which an active energy ray-curable resin composition containing an acrylic (meth) acrylate resin was used instead of the urethane (meth) acrylate resin. It was confirmed that the laminate using the active energy ray-curable resin composition was insufficient in film hardness and significantly insufficient in scratch resistance.
Comparative example 2 is an example of an active energy ray-curable resin composition using a (meth) acrylate compound containing no (meth) acryl having 1 or more and 2 or less (meth) acryl groups in one molecule. It was confirmed that the laminate using the active energy ray-curable resin composition was significantly insufficient in adhesion to the substrate after the light resistance test.
Comparative example 3 is an example of using an active energy ray-curable resin composition that does not contain a (meth) acrylate compound having 3 or more (meth) acryloyl groups in one molecule. It was confirmed that the coating film hardness of the laminate using the active energy ray-curable resin composition was significantly insufficient.
Comparative example 4 is an example in which the content of the (meth) acrylate compound having 1 or more and 2 or less (meth) acryloyl groups in one molecule in the active energy ray-curable resin composition is more than 50 mass%. It was confirmed that the coating film hardness and scratch resistance of the laminate using the active energy ray-curable resin composition were significantly insufficient.
Comparative example 5 is an example of using an active energy ray-curable resin composition containing a urethane (meth) acrylate resin having a weight average molecular weight of more than 30000. It was confirmed that the laminate using the active energy ray-curable resin composition failed to have all the properties.
Claims (11)
1. An active energy ray-curable resin composition characterized by comprising:
urethane (meth) acrylate resin (A),
A (meth) acrylate compound (B) having 1 or more and 2 or less (meth) acryloyl groups in one molecule,
A (meth) acrylate compound (C) having 3 or more (meth) acryloyl groups in one molecule,
the weight average molecular weight of the urethane (meth) acrylate resin (A) is in the range of 1500 to 30000,
the content of the (meth) acrylate compound (B) is in the range of 10 to 50 mass% based on the total mass of the urethane (meth) acrylate resin (A), the (meth) acrylate compound (B) and the (meth) acrylate compound (C),
the urethane (meth) acrylate resin (A) has a (meth) acryl equivalent in the range of 90 to 132 g/equivalent.
2. The active energy ray-curable resin composition according to claim 1, wherein the content of the urethane (meth) acrylate resin (a) is in a range of 20 to 80 mass% based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C).
3. The active energy ray-curable resin composition according to claim 1, wherein the (meth) acrylate compound (B) has an alkylene oxide chain.
4. The active energy ray-curable resin composition according to claim 3, wherein the average number of repetitions of the alkylene oxide chain is 4 or less.
5. The active energy ray-curable resin composition according to claim 1, wherein the content of the (meth) acrylate compound (C) is in a range of 5 to 50 mass% based on the total mass of the urethane (meth) acrylate resin (a), the (meth) acrylate compound (B) and the (meth) acrylate compound (C).
6. The active energy ray-curable resin composition according to claim 1, wherein the (meth) acrylate compound (C) contains one or more selected from the group consisting of pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.
7. A cured product comprising the active energy ray-curable resin composition according to any one of claims 1 to 6.
8. A laminate comprising a substrate and, on one or both sides thereof, a cured coating film of the active energy ray-curable resin composition according to any one of claims 1 to 6.
9. The laminate of claim 8, wherein the substrate is an acrylic substrate.
10. The laminate according to claim 8 or 9, wherein the substrate is in a film form.
11. An article comprising the laminate according to any one of claims 8 to 10 on a surface.
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| WO2023042922A1 (en) * | 2021-09-17 | 2023-03-23 | 三菱ケミカル株式会社 | Production method for multilayer film, prodcuction method for decorative melamine board, multilayer film, protective film for decorative melamine board, and decorative melamine board |
| JP7338029B1 (en) | 2022-12-27 | 2023-09-04 | 東洋インキＳｃホールディングス株式会社 | An active energy ray-curable composition for forming a hard coat layer, a hard coat film using the same, and a laminate thereof. |
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- 2020-04-07 WO PCT/JP2020/015722 patent/WO2020209264A1/en active Application Filing
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| Publication number | Publication date |
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| WO2020209264A1 (en) | 2020-10-15 |
| JPWO2020209264A1 (en) | 2021-10-07 |
| KR20210127750A (en) | 2021-10-22 |
| CN113661064A (en) | 2021-11-16 |
| TW202100600A (en) | 2021-01-01 |
| KR102564260B1 (en) | 2023-08-07 |
| TWI842870B (en) | 2024-05-21 |
| JP7131695B2 (en) | 2022-09-06 |
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