CN114316649A - Active energy ray-curable resin composition and laminate - Google Patents
Active energy ray-curable resin composition and laminate Download PDFInfo
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- CN114316649A CN114316649A CN202111142785.2A CN202111142785A CN114316649A CN 114316649 A CN114316649 A CN 114316649A CN 202111142785 A CN202111142785 A CN 202111142785A CN 114316649 A CN114316649 A CN 114316649A
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- acrylate
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- 239000011342 resin composition Substances 0.000 title claims abstract description 78
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 164
- 229920005989 resin Polymers 0.000 claims abstract description 62
- 239000011347 resin Substances 0.000 claims abstract description 53
- 239000000758 substrate Substances 0.000 claims abstract description 38
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims description 101
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 239000005056 polyisocyanate Substances 0.000 claims description 34
- 229920001228 polyisocyanate Polymers 0.000 claims description 34
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 23
- 239000002216 antistatic agent Substances 0.000 claims description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000007373 indentation Methods 0.000 abstract description 7
- 239000010410 layer Substances 0.000 description 61
- -1 acrylic ester Chemical class 0.000 description 57
- 239000002904 solvent Substances 0.000 description 34
- 239000007787 solid Substances 0.000 description 31
- 239000000126 substance Substances 0.000 description 31
- 150000002430 hydrocarbons Chemical group 0.000 description 30
- 238000000034 method Methods 0.000 description 28
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- 239000003999 initiator Substances 0.000 description 27
- 229920005862 polyol Polymers 0.000 description 25
- 239000000178 monomer Substances 0.000 description 23
- 150000003077 polyols Chemical class 0.000 description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 22
- 229920002554 vinyl polymer Polymers 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 19
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 125000002723 alicyclic group Chemical group 0.000 description 13
- 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 description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- 229920003023 plastic Polymers 0.000 description 11
- 239000004033 plastic Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 8
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229920006351 engineering plastic Polymers 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 229920000193 polymethacrylate Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-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
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 230000003373 anti-fouling effect Effects 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 125000005409 triarylsulfonium group Chemical group 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- 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 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 3
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
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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 3
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 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
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 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
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ASARMUCNOOHMLO-WLORSUFZSA-L cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2s)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O ASARMUCNOOHMLO-WLORSUFZSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- PFKRTWCFCOUBHS-UHFFFAOYSA-N dimethyl(octadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH+](C)C PFKRTWCFCOUBHS-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MFKHKJMRWGOTHL-UHFFFAOYSA-M ethyl(trioctyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CC)(CCCCCCCC)CCCCCCCC MFKHKJMRWGOTHL-UHFFFAOYSA-M 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 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
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 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
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-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
- 125000005474 octanoate group Chemical group 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- XDJFUWIQZPRDDG-UHFFFAOYSA-J prop-2-enoate;tin(4+) Chemical compound [Sn+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C XDJFUWIQZPRDDG-UHFFFAOYSA-J 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000010490 three component reaction Methods 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- UMMDBKGUDMBUSR-UHFFFAOYSA-M tris-decyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC UMMDBKGUDMBUSR-UHFFFAOYSA-M 0.000 description 1
- 150000007971 urates Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 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
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
- 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
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- 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
- C08F220/22—Esters containing halogen
-
- 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
- C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Abstract
The invention provides an active energy ray-curable resin composition and a laminate. The invention provides an active energy ray-curable resin composition for forming a resin layer in a laminate comprising a substrate and the resin layer, the active energy ray-curable resin composition being characterized in thatThe line-hardening type resin composition comprises: a (meth) acrylate (A) and a compound (B) having a fluorine atom, and satisfies the following conditions 1 and 2. Condition 1: indentation hardness (N/mm) of resin layer2) Is 450 or more and 600 or less. Condition 2: the elongation at break of the resin layer is 3.7% or more and 10.0% or less.
Description
Technical Field
The present invention relates to an active energy ray-curable resin composition and a laminate.
Background
Various plastics have been used in various fields such as a main body of a home appliance such as a refrigerator, a television, and an air conditioner, a remote controller thereof, a housing and a display of an information terminal such as a mobile phone, a smartphone, an input board, and a personal computer, automobile parts, and automobile interior materials. Plastics and the like have advantages such as processability, transparency, lightweight properties, and low cost, but have a disadvantage of being relatively easily scratched.
In order to improve these disadvantages, a resin layer having excellent scratch resistance is provided on the surface of plastic or the like, and the scratch resistance of the surface is improved without impairing the advantages of the plastic or the like.
[ Prior art documents ]
[ patent document ]
[ patent document 1] Japanese patent laid-open No. 2004-
Disclosure of Invention
[ problems to be solved by the invention ]
Recently, flexible displays, smart phones, and the like have attracted attention, and scratch resistance and flexibility are required for these devices. Patent document 1 discloses a resin layer having excellent abrasion resistance, but does not describe flexibility required for a flexible display or a smart phone.
[ means for solving problems ]
The present inventors have made extensive studies and as a result, have found that the above problems can be solved by a predetermined active energy ray-curable resin composition and a laminate. The present invention has been made to solve at least part of the above problems, and can be realized as the following embodiments or application examples.
According to the present invention, the following items are provided.
(item 1)
An active energy ray-curable resin composition constituting a resin layer in a laminate having a substrate and a resin layer, the active energy ray-curable resin composition comprising:
(meth) acrylic acid ester (A), and
a compound (B) having a fluorine atom, and
the following conditions 1 and 2 are satisfied.
Condition 1: indentation hardness (N/mm) of resin layer2) Is 450 or more and 600 or less.
Condition 2: the elongation at break of the resin layer is 3.7% or more and 10.0% or less.
(item 2)
The active energy ray-curable resin composition according to item 1, wherein the component (A) comprises a urethane (meth) acrylate (a1) and/or a hydroxyl group-containing (meth) acrylate (a 2).
(item 3)
The active energy ray-curable resin composition according to item 2, wherein the component (a1) is a reaction product of a polyisocyanate (a1-1) and a hydroxyl group-containing (meth) acrylate (a1-2), and the mass ratio ((a1-1)/(a1-2)) of the component (a1-1) to the component (a1-2) is 15/85 to 50/50.
(item 4)
The active energy ray-curable resin composition according to any one of items 1 to 3, wherein the component (B) is a compound having a fluorine atom and a polymerizable unsaturated group.
(item 5)
The active energy ray-curable resin composition according to any one of items 1 to 4, comprising an antistatic agent (C).
(item 6)
The active energy ray-curable resin composition according to any one of items 1 to 5, wherein the component (C) is a polymer having a quaternary ammonium salt group.
(item 7)
A laminate comprising a substrate and a resin layer, wherein the resin layer is a cured product of the active energy ray-curable resin composition according to any one of items 1 to 6.
[ Effect of the invention ]
The laminate comprising the resin layer composed of the active energy ray-curable resin composition provided by the present invention is excellent in scratch resistance and flexibility.
Drawings
Is free of
Detailed Description
In the entire present invention, the ranges of numerical values such as the physical property values and the contents may be appropriately set (for example, selected from the upper limit and the lower limit described in the following items). Specifically, as for the numerical value α, when the lower limit of the numerical value α is exemplified by a1, a2, A3, and the like, and the upper limit of the numerical value α is exemplified by B1, B2, B3, and the like, the range of the numerical value α can be exemplified by a1 or more, a2 or more, A3 or more, B1 or less, B2 or less, B3 or less, a1 to B1, a1 to B2, a1 to B3, a2 to B1, a2 to B2, a2 to B3, A3 to B1, A3 to B2, A3 to B3, and the like. In the present invention, "to" is used to include numerical values described before and after the "to" as the lower limit value and the upper limit value. The components, resin layer, laminate, and the like constituting the active energy ray-curable resin composition provided in the present invention will be described in detail below.
< (meth) acrylic ester (A) >
Examples of the (meth) acrylic acid ester (a) (also referred to as "component (a)" in the present invention) include: a (meth) acrylate containing a chain hydrocarbon group, a (meth) acrylate containing an alicyclic hydrocarbon group, a (meth) acrylate containing an aromatic hydrocarbon group, a (meth) acrylate containing a heterocycle, and the like. (A) The component (b) can be obtained, for example, by reacting monomers with each other. In the present invention, a chain structure means a structure having no cyclic structure, and may include a linear structure and/or a branched structure.
Examples of the (meth) acrylate containing a chain hydrocarbon group include: mono (meth) acrylates containing a chain hydrocarbon group, di (meth) acrylates containing a chain hydrocarbon group, tri (meth) acrylates containing a chain hydrocarbon group, tetra (meth) acrylates containing a chain hydrocarbon group, penta (meth) acrylates containing a chain hydrocarbon group, hexa (meth) acrylates containing a chain hydrocarbon group, and the like.
Examples of the mono (meth) acrylate containing a chain hydrocarbon group include: mono (meth) acrylate having an alkyl group with a carbon number of about 1 to 20, ethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, butylene glycol mono (meth) acrylate, pentanediol mono (meth) acrylate, hexanediol mono (meth) acrylate, diethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, triethylene glycol mono (meth) acrylate, tripropylene glycol mono (meth) acrylate, tetraethylene glycol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, ethoxylated neopentyl glycol mono (meth) acrylate, hydroxypivalic acid neopentyl glycol mono (meth) acrylate, trimethylolpropane mono (meth) acrylate, propylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, propylene glycol (acrylate, propylene glycol mono (meth) acrylate, propylene glycol mono (acrylate, propylene glycol mono, Ethoxylated trimethylolpropane mono (meth) acrylate, propoxylated trimethylolpropane mono (meth) acrylate, tris (2-hydroxyethyl) isocyanurate mono (meth) acrylate, glycerol mono (meth) acrylate, and the like.
Examples of the di (meth) acrylate containing a chain hydrocarbon group include: 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, butanediol di (meth) acrylate, bis (methacryloyloxy) propanol, decanediol di (meth) acrylate, hexanediol di (meth) acrylate, nonanediol di (meth) acrylate, polytetraethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and the like.
Examples of the tri (meth) acrylate containing a chain hydrocarbon group include: pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, glycerol tri (meth) acrylate, sorbitol tri (meth) acrylate, tris 2-hydroxyethyl isocyanurate tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, Ethylene Oxide (EO) -modified trimethylolpropane tri (meth) acrylate, Propylene Oxide (PO) -modified trimethylolpropane tri (meth) acrylate, EO-modified phosphoric acid tri (meth) acrylate, trimethylolethane tri (meth) acrylate, ethoxylated isocyanurate tri (meth) acrylate, and the like.
Examples of the tetra (meth) acrylate containing a chain hydrocarbon group include: pentaerythritol tetra (meth) acrylate, di-trimethylolpropane tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, sorbitol tetra (meth) acrylate, and the like.
Examples of the penta (meth) acrylate containing a chain hydrocarbon group include: dipentaerythritol penta (meth) acrylate, sorbitol penta (meth) acrylate, di-trimethylolpropane penta (meth) acrylate, and the like.
Examples of the hexa (meth) acrylate containing a chain hydrocarbon group include: dipentaerythritol hexa (meth) acrylate, di-trimethylolpropane hexa (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate, hexafunctional aliphatic urethane (meth) acrylate (product name "Miramer PU-610", manufactured by Miwon Specialty chemicals) and the like.
Examples of the other (meth) acrylate containing a chain hydrocarbon group include 16-to 20-functional acrylates containing a dendritic polymer structure (products of "Sirius-501", "SUBARU-501", manufactured by osaka organic chemical industry (japan) ").
Examples of the (meth) acrylate containing an alicyclic hydrocarbon group include tricyclodecane dimethanol di (meth) acrylate and dimethylol tricyclodecane di (meth) acrylate.
Examples of the aromatic hydrocarbon group-containing (meth) acrylate include: bisphenol a di (meth) acrylate, 9-bis [4- (2- (meth) acryloyloxyethoxy) phenyl ] fluorene, bis (meth) acrylic acid [3,3'- [ isopropylidenebis (p-phenylene oxy) ] bis (2-hydroxypropane) ] -1,1' -diyl, bisphenol a diglycidyl ether (meth) acrylic acid adduct, and the like. Furthermore, (meth) acrylic acid means methacrylic acid and/or acrylic acid.
Examples of the (meth) acrylate containing a heterocycle include ethoxylated isocyanurate tri (meth) acrylate and caprolactone-modified tris ((meth) acryloyloxyethyl) isocyanurate.
Examples of other (meth) acrylates include: urethane (meth) acrylates, polyester (meth) acrylates, epoxy (meth) acrylates, and the like.
As a method for synthesizing urethane (meth) acrylate, various known methods can be exemplified. Examples of the known various synthetic methods for urethane (meth) acrylate include:
(1) a method of further subjecting a hydroxyl group-containing (meth) acrylate to a urethanization reaction with an isocyanate group-containing prepolymer obtained by urethanizing a polyol with a polyisocyanate,
(2) A method of reacting an isocyanate group-containing (meth) acrylate with a prepolymer having a hydroxyl group obtained by further subjecting a polyol and a polyisocyanate to a urethane-forming reaction,
(3) A process for reacting a polyisocyanate with a hydroxyl group-containing (meth) acrylate,
(4) A method of reacting a polyol with an isocyanate group-containing (meth) acrylate, and the like.
In the method for synthesizing urethane (meth) acrylate, various known catalysts (dibutyltin dilaurate and the like) can be suitably used as needed.
In the method for synthesizing urethane (meth) acrylate, the urethane (meth) acrylate can be obtained by reacting the respective components at a temperature or under a pressure at which the urethane-forming reaction is carried out.
Examples of the polyol include: polyether polyol, polyester polyol, polycarbonate polyol, acrylic polyol, polyolefin polyol, neopentyl glycol, 3-methyl-1, 5-pentanediol, ethylene glycol, propylene glycol, 1, 4-butanediol, 1, 6-hexanediol, trimethylolpropane, pentaerythritol, tricyclodecane dimethylol, bis- [ hydroxymethyl ] -cyclohexane, and the like. The polyhydric alcohol exemplified above and the polyhydric alcohol known per se can be used alone or in combination of two or more.
Examples of the polyether polyol include polyalkylene glycol (such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol). As the polyether polyol, commercially available products can also be used. Examples of the product include products such as "adi Polyether (ADEKA Polyether) P series", "adi Polyether (ADEKA Polyether) G series", "adi Polyether (ADEKA Polyether) EDP series" (manufactured by adi (ADEKA) (stock)), and the like.
Examples of the polyester polyol include those obtained by the reaction of a polyol with a polycarboxylic acid (succinic acid, phthalic acid, malonic acid, maleic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, etc.), ring-opened polymers of cyclic esters (propiolactone, β -methyl- δ -valerolactone, e-caprolactone, etc.), and three-component reaction products of a polyol with a polycarboxylic acid and a cyclic ester. As the polyester polyol, a commercially available product can be used. As the product, there can be exemplified: the product names "Cola Polyol (Kuraray Polyol) P series", "Cola Polyol (Kuraray Polyol) F series" (manufactured by Cola (Kuraray) (Co., Ltd.)), the product name "Placeel (Placel) 205" (manufactured by Daicel (Co., Ltd.)), the product name "Polilate (Polylite) OD-X-2155" (manufactured by Di Sheng (DIC) (Co., Ltd.)), and the like.
Examples of the polycarbonate polyol include a reaction product of a polyol and phosgene (phosgene), a ring-opened polymer of a cyclic carbonate (e.g., alkylene carbonate), and the like. Examples of the alkylene carbonate include: ethylene carbonate, trimethylene carbonate, tetramethylene carbonate, hexamethylene carbonate, and the like. As the polycarbonate polyol, a commercially available product can be used. The product may be named "kohler Polyol (Kuraray Polyol) C series" (manufactured by kohler corporation), for example.
Examples of the acrylic polyol include homopolymers or copolymers of acrylic monomers each having one or more hydroxyl groups in one molecule, and copolymers obtained by copolymerizing other monomers with these copolymers. As the acrylic polyol, a commercially available product can be used. The product may be named "Yajiaofeng UH-2000 series" (manufactured by east Asia corporation), for example.
As the polyolefin polyol, there can be exemplified: polybutadiene, hydrogenated polybutadiene, polyisoprene, hydrogenated polyisoprene, chlorides of these, and the like, which contain two or more hydroxyl groups. As the polyolefin polyol, commercially available products can also be used. Examples of the product include "Nissan (NISSO) -PB GI series" (manufactured by Nissan Co., Ltd.).
Examples of the polyisocyanate include: polyisocyanates containing chain hydrocarbon groups, polyisocyanates containing alicyclic hydrocarbon groups, polyisocyanates containing aromatic hydrocarbon groups, and the like. Examples of the polyisocyanate containing a chain hydrocarbon group include hexamethylene diisocyanate. Examples of the alicyclic hydrocarbon group-containing polyisocyanate include isophorone diisocyanate, dicyclohexylmethane diisocyanate, and the like. Examples of the polyisocyanate containing an aromatic hydrocarbon group include: toluene diisocyanate, xylene diisocyanate, diphenylmethane-4, 4' -diisocyanate, 3-methyl diphenylmethane diisocyanate, and the like. Examples of other polyisocyanates include: 1, 5-naphthalene diisocyanate, the above-mentioned exemplified polyisocyanates or adducts of various known polyisocyanates, polymers of these isocyanates, and the like. Examples of such polyisocyanates include: biurets, urates, adducts, allophanates (allophanates), and the like. Examples of the Biuret of the polyisocyanate include those having the names "Polydande (Duranate) 24A-100", "Biuret (Biuret) 22A-75P" and "Biuret (Biuret) 21S-75E" (all manufactured by Asahi chemical (Strand)). Examples of the uric acid ester of polyisocyanate include those having the trade names "crotonate HK" and "crotonate HXR" (all manufactured by tokoa (stock)). Examples of the adduct of polyisocyanate include "crotonate HL" (manufactured by tokyo (r) ") and the like. Examples of the allophanate of the polyisocyanate include "crotonate" 2770 "(manufactured by Tosoh corporation). The polyisocyanate of the present invention is also a polyisocyanate having an average isocyanate number of 3 or more and 10 or less. The average number of isocyanate groups can be calculated by the following formula. Average isocyanate group number ═ (number average molecular weight (Mn) × isocyanate group concentration (%)/(42.02 × 100). The isocyanate group concentration (%) in the formula (I) is determined by the following method in accordance with Japanese Industrial Standards (JIS) K1603-1: 2007. The polyisocyanate exemplified above and the polyisocyanate known per se can be used alone or in combination of two or more.
Examples of the hydroxyl group-containing (meth) acrylate include: hydroxyl group-containing (meth) acrylates containing chain hydrocarbon groups, hydroxyl group-containing (meth) acrylates containing alicyclic hydrocarbon groups, hydroxyl group-containing (meth) acrylates containing aromatic hydrocarbon groups, and the like. Examples of the hydroxyl group-containing (meth) acrylate containing a chain hydrocarbon group include: 1-hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and the like. Examples of the hydroxyl group-containing (meth) acrylate containing an alicyclic hydrocarbon group include methyl 4- (hydroxymethyl) cyclohexyl (meth) acrylate and the like. Examples of the hydroxyl group-containing (meth) acrylate containing an aromatic hydrocarbon group include hydroxyphenyl (meth) acrylate and the like. The hydroxyl group-containing (meth) acrylate exemplified above and the hydroxyl group-containing (meth) acrylate known per se may be used alone or in combination of two or more.
Examples of the isocyanate group-containing (meth) acrylate include: 2-isocyanatoethyl (meth) acrylate, 2- (2- (meth) acryloyloxyethyloxy) ethyl isocyanate, 1- (bis (meth) acryloyloxymethyl) ethyl isocyanate, and the like. The isocyanate group-containing (meth) acrylate exemplified above and the isocyanate group-containing (meth) acrylate known in the art may be used alone or in combination of two or more.
Various known methods can be exemplified as a method for synthesizing the polyester (meth) acrylate. Examples of the various known synthetic methods for polyester (meth) acrylate include:
(1) a method of reacting a carboxyl group-containing (meth) acrylate (carboxyethyl (meth) acrylate, carboxypolycaprolactone mono (meth) acrylate, etc.) with a hydroxyl-terminated polyester obtained by reacting a polycarboxylic acid with a polyhydric alcohol,
(2) A method of reacting a carboxyl-terminated polyester obtained by reacting a polycarboxylic acid with a polyhydric alcohol with a hydroxyl-containing (meth) acrylate.
In these methods, various known catalysts can be suitably used as needed.
Examples of the epoxy (meth) acrylate include those obtained by addition reaction of a carboxyl group-containing (meth) acrylate and an epoxy resin containing at least two epoxy groups in one molecule (e.g., a bisphenol a type epoxy resin, a bisphenol F type epoxy resin, and a biphenol type epoxy resin).
In these methods, various known catalysts can be suitably used as needed.
(A) Commercially available products can be used as the components. As the product, there can be exemplified: pentaerythritol triacrylate ((product name "a-TMM-3", "a-TMM-3L", manufactured by maizhou chemical industry (stock)), (product name "Miramer) M301", manufactured by Meiyuan (MIWON) corporation), (product name "arinexus (Aronix) M-309", manufactured by east asian synthesis (stock)), di-trimethylolpropane tetraacrylate (product name "arinexus (Aronix) M-408", manufactured by east asian synthesis (stock)), ethoxylated pentaerythritol tetra (meth) acrylate (product name "SR 494", manufactured by Sartomer), dipentaerythritol penta (meth) acrylate (product name "SR 399", manufactured by Sartomer), a mixture of dipentaerythritol poly (meth) acrylate (dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate) ((product name "yakara (ka) DPHA", manufactured by nipponica chemicals (stock)), (manufactured under the name "a-9550", manufactured by shinzhou chemical industry (stock)), (manufactured under the names "arionix (Aronix) M-403", "arionix (Aronix) M-400", "arionix (Aronix) M-402", "arionix (Aronix) M-404", "arionix (aronia) M-405", "arionix (aronia) M-406", manufactured by east asia synthesis (stock)), Tripentaerythritol poly (meth) acrylate (manufactured under the name "Biscoat) #802, Tripentaerythritol acrylate (Tripentaerythritol acrylate, TriPEA)", manufactured by osaka organic chemical industry (stock)), multifunctional acrylate containing a dendrimer structure (manufactured under the names "Sirius) -501", "subasolus (baa) -501", manufactured by saka organic chemical industry (stock) ", and (manufactured by saka) chemical industry (stock)", manufactured by seiki chemical industry (stock) " Urethane (meth) acrylate ((product name "UV 1700B", "UV 7620 EA", "UV 7610B", "UV 7600B", "UV 7650B", manufactured by Mitsubishi Chemical Co., Ltd.), (product name "DPHA 40H", "UX 5003", manufactured by Nippon Chemical Co., Ltd.), (product name "Bishite (BEAMSET) 577", manufactured by Mitsuka Chemical industry Co., Ltd.), (product name "8 UX-015A", manufactured by Dazakichen Chemical industry Co., Ltd.), (product name "U15 HA", manufactured by Newzhongcun Chemical industry Co., Ltd.), (product name "Miramer) PU 610", manufactured by Meiyuan Special Chemical industry (Miwon Chemical Co., Ltd.), (product name "Euter (Etercure) 6196-100", manufactured by Changxing Materials Co., Ltd.), bisphenol A type epoxy acrylate (product name "Aronix OT-2501", manufactured by Toyo Seiya Kabushiki Kaisha, etc.).
The substances exemplified as the component (a) and the substances known as the component (a) may be used alone or in combination of two or more. (A) Component (b) is preferably urethane (meth) acrylate (a1) and/or hydroxyl group-containing (meth) acrylate (a 2). By using the component (a1), the balance between flexibility and abrasion resistance is improved. The component (a2) is preferably high in reactivity because the cured product of the active energy ray-curable resin composition of the present invention has high hardness. (a1) The component (b) is more preferably a reaction product of a polyisocyanate (a1-1) (also referred to as a "(a 1-1) component" in the present invention) and a hydroxyl group-containing (meth) acrylate (a1-2) (also referred to as a "(a 1-2) component" in the present invention), and still more preferably at least one member selected from the group consisting of a polyisocyanate containing a chain hydrocarbon group, a polyisocyanate containing an alicyclic hydrocarbon group, a biuret of a polyisocyanate containing a chain hydrocarbon group, a biuret of a polyisocyanate containing an alicyclic hydrocarbon group, an uretonate of a polyisocyanate containing a chain hydrocarbon group, an adduct of a polyisocyanate containing an alicyclic hydrocarbon group, an allophanate of a polyisocyanate containing a chain hydrocarbon group and an allophanate of a polyisocyanate containing an alicyclic hydrocarbon group, and a hydroxyl group-containing (meth) containing a chain hydrocarbon group Reaction products of acrylates. (a2) The component (b) is more preferably a hydroxyl group-containing (meth) acrylate containing a chain hydrocarbon group. (A) Component (c) is preferred because it has two or more (meth) acryloyl groups and is excellent in scratch resistance.
The content ratio (mass ratio, in terms of solid content, [ (a 1-1)/a 1-2) of the polyisocyanate (a1-1) and the hydroxyl group-containing (meth) acrylate (a1-2) constituting the urethane (meth) acrylate (a1) may be as follows: 50/50, 45/55, 40/60, 35/65, 30/70, 29/71, 28/72, 27/73, 26/74, 25/75, 20/80, etc., the lower limit can be exemplified by: 45/55, 40/60, 35/65, 30/70, 29/71, 28/72, 27/73, 26/74, 25/75, 20/80, 15/85, and the like. In one embodiment, the content ratio (mass ratio, in terms of solid content, [ (a1-1) component/(a 1-2) component ]) of the component (a1-1) to the component (a1-2) is preferably about 15/85 to 50/50.
The upper limit of the number of isocyanate groups in one molecule of the component (a1-1) may be 10, 9, 8, 7, 6,5, 4, 3, etc., and the lower limit may be 9, 8, 7, 6,5, 4, 3, 2, etc. In one embodiment, the number of isocyanate groups in one molecule of the component (a1-1) is preferably about 2 to 10.
When two or more of the components (a) are used in combination, it is considered that the components (a) each include various kinds within a range of about 8. For example, when two kinds of the component (a) are used in combination, the first is the component (a1) and the second is the component (a2), the upper limit of the content ratio (mass ratio, conversion of solid content, [ (a1) component/(a 2) component) may be 80/20, 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, 45/55, 40/60, 35/65, 30/70, 25/75, etc., and the lower limit thereof may be 75/25, 70/30, 65/35, 60/40, 55/45, 50/50, 45/55, 40/60, 35/65, 30/70, 25/75, 20/80, etc. In one embodiment, the content ratio (mass ratio, in terms of solid content, [ (a1) component/(a 2) component ]) of the component (a1) to the component (a2) is preferably about 20/80 to 80/20.
Examples of the upper limit of the number of (meth) acryloyl groups in the hydroxyl group-containing (meth) acrylate used as the component (a1) and/or the component (a2) include 9, 8, 7, 6,5, 4, 3, and 2, and examples of the lower limit include 8, 7, 6,5, 4, 3, 2, and 1. In one embodiment, the hydroxyl group-containing (meth) acrylate used as the component (a1) and/or the component (a2) preferably has a number of (meth) acryloyl groups of about 1 to 9, more preferably about 2 to 4. When the upper limit or less is set, the resin layer is more excellent in flexibility.
(A) Examples of the upper limit of the molecular weight of the component (a) include 50,000, 40,000, 30,000, 20,000, 10,000, 5,000, 1,000, 500, 250, 100 and the like, and examples of the lower limit thereof include 40,000, 30,000, 20,000, 10,000, 5,000, 1,000, 500, 250, 100, 50 and the like. In one embodiment, the molecular weight of the component (A) is preferably about 50 to 50,000.
(A) Examples of the upper limit of the content (in terms of solid content) of the component (a) in 100% by mass of the total structural units in terms of solid content of the component (a) and the component (B) in the present invention include 99.9% by mass, 99.5% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 85% by mass, 80% by mass, and 75% by mass, and examples of the lower limit thereof include 99.5% by mass, 99% by mass, 98% by mass, 97% by mass, 96% by mass, 95% by mass, 94% by mass, 93% by mass, 92% by mass, 91% by mass, 90% by mass, 85% by mass, 80% by mass, 75% by mass, and 70% by mass. In one embodiment, the content of the component (a) in 100% by mass of the total structural units of the components (a) and (B) in terms of solid content in the present invention (in terms of solid content) is preferably about 70% by mass to 99.9% by mass, more preferably 80% by mass to 99.9% by mass, even more preferably 85% by mass to 99.9% by mass, and particularly preferably 90% by mass to 99.9% by mass, in order to satisfactorily exhibit the effects of the present invention.
< Compound (B) having fluorine atom >
The active energy ray-curable resin composition of the present invention contains a compound (B) having a fluorine atom (also referred to as "component (B)" in the present invention). (B) The component (C) may have a polymerizable unsaturated group in addition to the fluorine atom. That is, examples of the component (B) include a compound having a fluorine atom and no polymerizable unsaturated group, a compound having a fluorine atom and a polymerizable unsaturated group, and the like. Examples of the polymerizable unsaturated group include a carbon-carbon double bond and a carbon-carbon triple bond. Specific examples of the polymerizable unsaturated group include a vinyl group and a (meth) acryloyl group. (B) The component (B) is an agent which can be used as an antifouling agent.
(B) Commercially available products can be used as the components. As the product, there can be exemplified: the product names "OPTOOL (OPTOOL) DAC-HP", "OPTOOL (OPTOOL) DSX-E", "OPTOOL (OPTOOL) UD 120" (manufactured by Dajin industry (R.A.)), the product names "Megafac (Megafac) RS 75", "Megafac (Megafac) RS 76-E", "Megafac (Megafac) RS 76-NS", "Megafac (Megafac) RS 851", "Megafac (Megafac) RS 852", "Megafac (Megafac) RS 853", "Megafac (Megafac) RS 854" (manufactured by Dige. DIC (D) (G.A.), the product names "X71-1203M" (manufactured by Bessen. Chem (G.)), the product names "SUA 1900L 10", "SUA 1900L 6" (manufactured by New Mesochen chemical industry (R.A.), the product names "Foster (F.)" Ft) (Ft.), "Ft 710", "Ft (Ft) (Ft.)," Ft 710 "," Ft., "Foger (Ftergent)601 AD", "Foger (Ftergent)601ADH 2", "Foger (Ftergent) 602A", "Foger (Ftergent)650 AC", "Foger (Ftergent) 681" (manufactured by Neios (Neos) (Strand)), and the like.
The substances exemplified as the component (B) and the substances known as the component (B) may be used alone or in combination of two or more. The component (B) is a compound having a fluorine atom and a polymerizable unsaturated group, and is excellent in scratch resistance and abrasion resistance. When the component (B) further contains silicon, the cured product of the active energy ray-curable resin composition of the present invention can slide well, and therefore, it is preferable.
(A) Examples of the upper limit of the content ratio (mass ratio, solid content conversion, [ (A) component/(B) component ]) of the component (B) include 99.9/0.1, 99.8/0.2, 99.7/0.3, 99.6/0.4, 99.5/0.5, 99.4/0.6, 99.3/0.7, 99.2/0.8, 99.1/0.9, 99/1, 98/2, 97/3, 96/4, 95/5 and 90/10, and examples of the lower limit thereof include 99.8/0.2, 99.7/0.3, 99.6/0.4, 99.5/0.5, 99.4/0.6, 99.3/0.7, 99.2/0.8, 99.1/0.9, 99/1, 98/2, 97/3, 96/4, 95/5, 90/10 and 85/15. In one embodiment, the content ratio of the component (a) to the component (B) (in terms of solid content, [ (a) component/(B) component ]) is preferably about 85/15 to 99.9/0.1, from the viewpoint of satisfactorily exhibiting the effects of the present invention.
(B) The upper limit of the content (in terms of solid content) of the component (a) and the component (B) in 100% by mass of the total structural units in terms of solid content in the present invention may be 15% by mass, 10% by mass, 9% by mass, 7% by mass, 5% by mass, 3% by mass, 1% by mass, 0.9% by mass, 0.7% by mass, 0.5% by mass, 0.3% by mass, 0.1% by mass, or the like, and the lower limit may be 10% by mass, 9% by mass, 7% by mass, 5% by mass, 3% by mass, 1% by mass, 0.9% by mass, 0.7% by mass, 0.5% by mass, 0.3% by mass, 0.1% by mass, 0.05% by mass, or the like. In one embodiment, the content of the component (B) in 100% by mass of the total structural units of the components (a) and (B) in terms of solid content in the present invention (in terms of solid content) is preferably about 0.05% by mass to 15% by mass, more preferably 0.05% by mass to 10% by mass, even more preferably 0.05% by mass to 5% by mass, particularly preferably 0.05% by mass to 3% by mass, and even more preferably 0.05% by mass to 1% by mass. When the content is not less than the lower limit, the effect as an antifouling agent can be sufficiently exhibited. When the content is not more than the upper limit, compatibility with other components becomes good, and the resin layer has excellent transparency.
< antistatic agent (C) >
The active energy ray-curable resin composition of the present invention contains an antistatic agent (C) (also referred to as "component (C)" herein). Examples of antistatic agents include: anionic antistatic agents, cationic antistatic agents, nonionic antistatic agents, antistatic agents using alkali metal salts, and the like.
Examples of the anionic antistatic agent include: sulfonic acid type, sulfate type, phosphorus-containing type, and the like. Examples of the sulfonic acid type include: alkyl sulfonates, alkyl benzene sulfonates, alkyl naphthalene sulfonates, alkyl diphenyl sulfonates, and the like. Examples of the sulfate ester type include: alkyl sulfates, alkyl ethoxy sulfates, and the like. Examples of the phosphorus-containing type include: alkyl phosphates, alkyl phosphites, alkyl phosphonic acids, alkyl phosphonates, and the like.
Examples of the cationic antistatic agent include: aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts, and the like.
Examples of quaternary ammonium salts include: quaternary ammonium salts containing a hydrocarbon group, quaternary ammonium salts containing a nitrogen ring, polymers having a quaternary ammonium salt group, and the like.
The quaternary ammonium salts containing a hydrocarbon group mean quaternary ammonium salts which may contain any of an alkyl group, a benzene ring, and an alicyclic ring. Examples of the quaternary ammonium salt containing a hydrocarbon group include: trioctyl (octyi) methyl ammonium chloride, trioctyl ethyl ammonium chloride, tridecyl methyl ammonium chloride, dilauryl dimethyl ammonium chloride, lauryl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride, stearyl dimethyl ammonium chloride, trioctyl (capryl) methyl ammonium chloride, tetrabutyl ammonium chloride, benzyl trimethyl ammonium chloride, benzyl triethyl ammonium chloride, and the like. And may be a bromide, iodide, sulfite, sulfate or bisulfate of these.
Examples of the quaternary ammonium salts having a nitrogen-containing ring include quaternary ammonium salts having a nitrogen ring including a pyridine ring, a picoline ring, a quinoline ring, an imidazoline ring, and a morpholine ring. The nitrogen-containing quaternary ammonium salts may have a straight or branched alkyl group. When the nitrogen ring-containing quaternary ammonium salt has a linear or branched alkyl group, the number of carbons in the alkyl group may be 30, 25, 20, 15, 10, 8, 6, or the like as an upper limit, and 25, 20, 15, 10, 8, 6, or 4 as a lower limit. In one embodiment, when the nitrogen ring-containing quaternary ammonium salt has a straight or branched alkyl group, the number of carbon atoms in the alkyl group is preferably about 4 to 30. In addition, the quaternary ammonium salts of the nitrogen-containing ring may be bromides, iodides, sulfites, sulfates or bisulfates of these.
As the polymer having a quaternary ammonium salt group, polymers shown in Japanese patent laid-open Nos. Hei 9-194528, Hei 11-60614, Hei 2014-003104 and Hei 2016-003283 can be exemplified.
The polymer having a quaternary ammonium salt group is, for example, a copolymer obtained by polymerizing a vinyl monomer (c1) having a quaternary ammonium salt structure (herein, also referred to as a "c 1 component"), a vinyl monomer (c2) having a weight average molecular weight of 4,000 to 10,000 (herein, also referred to as a "c 2 component") obtained by ring-opening polymerization of a hydroxyl group-containing vinyl monomer and a lactone, a vinyl monomer (c3) having a branched alkyl ester group having 3 to 5 carbon atoms and having no alicyclic structure (herein, also referred to as a "c 3 component"), and, if necessary, a vinyl monomer (c4) (herein, also referred to as a "c 4 component") other than these at a predetermined mass ratio.
(c1) The component (C) is not particularly limited as long as it is a vinyl monomer having a quaternary ammonium salt structure in the molecule. (c1) The component (b) is preferably represented by formula (1): CH (CH)2＝C(R1)-CO-A-B-N+(R2)(R3)(R4)·X-(in the formula, R1Represents H or CH3，R2～R4A (meth) acrylate compound represented by an alkyl group having 1 to about 3 carbon atoms, A represents O or NH, B represents an alkylene group having 1 to about 3 carbon atoms, and X represents a counter anion species). As X-Examples thereof include: cl-、SO4 2-、SO3 -、C2H5SO4 -、Br-And the like. In terms of antistatic ability of component (C), X-Most preferably Cl-. Examples of commercially available products of component (c1) include a product name "Lyte Ester (Light Ester) DQ-100", manufactured by KJ Chemicals (Co., Ltd.), and a product name "DMAEA-Q".
(c2) The component (b) is a component obtained by ring-opening polyaddition reaction of a hydroxyl group-containing vinyl monomer and a lactone, and can be used without particular limitation. In addition, when another long-chain monomer (e.g., a vinyl monomer having an alkylene oxide structure with an alkyl terminal in the molecule) is used instead of the component (C2), the antistatic ability of the component (C) tends to be insufficient. Examples of the hydroxyl group-containing vinyl monomers include hydroxyl group-containing (meth) acrylates and hydroxyl group-containing vinyl monomers. Examples of the hydroxyl group-containing (meth) acrylate include: hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxyethyl (meth) acryloylamide, and the like. Examples of the hydroxyl group-containing vinyl monomer include: hydroxyethyl vinyl ether, hydroxybutyl vinyl ether, hydroxydiethylene glycol vinyl ether, and the like. In particular, the hydroxyl group-containing vinyl monomer is preferably a hydroxyl group-containing (meth) acrylate in terms of radical copolymerizability. Examples of the lactone include: beta-propiolactone, gamma-butyrolactone, delta-valerolactone, beta-methyl-delta-valerolactone, epsilon-caprolactone and the like. In particular, the lactone group is preferably epsilon-caprolactone and/or delta-valerolactone in view of the reactivity of the ring-opening polymerization.
Various known methods can be exemplified as a method for synthesizing the component (c 2). (c2) Specific examples of the method for synthesizing the component (a) include a method in which the lactone is subjected to a ring-opening polyaddition reaction using the hydroxyl group-containing vinyl monomer as an initiator. The weight average molecular weight is achieved by repeating the polyester structure by appropriately selecting the charging ratio of the hydroxyl group-containing vinyl monomers and the lactones, or the reaction temperature, the kind and/or amount of the catalyst. Examples of the catalyst in the ring-opening polyaddition reaction include: inorganic acids, alkali metals, lithium compounds, tin compounds, metal alkoxides, and the like. Examples of the inorganic acid include sulfuric acid and phosphoric acid. Examples of the alkali metal include: lithium, sodium, potassium, and the like. Examples of the lithium compound include n-butyllithium and t-butyllithium. Examples of the tin compound include: dibutyltin dilaurate, dibutyltin dioctoate (octoate), dibutyltin mercaptide, tin acrylate, and the like. Examples of the metal alkoxide include titanium tetrabutoxide and the like. The amount of the catalyst used in the ring-opening polyaddition reaction is usually about 0.01 to 10% by mass based on 100% by mass of the total of the hydroxyl group-containing vinyl monomers and lactones. (c2) The upper limit of the weight average molecular weight of the component (b) may be exemplified by: 10,000, 9,500, 9,000, 8,500, 8,000, 7,500, 7,000, 6,500, 6,000, 5,500, 5,000, 4,500, 4,000, etc., the lower limit may be exemplified by: 9,500, 9,000, 8,500, 8,000, 7,500, 7,000, 6,500, 6,000, 5,500, 5,000, 4,500, 4,000, etc. In one embodiment, the molecular weight of the component (c2) is preferably about 4,000 to 10,000. When the weight average molecular weight of the component (C2) is less than 4000, the compatibility between the component (A) and the component (C) becomes insufficient, and the active energy ray-curable resin composition tends to be turbid or the transparency of the cured product tends to be impaired. (c2) When the weight average molecular weight of the component exceeds 10000, the synthesis is difficult. In the present invention, the weight average molecular weight means a polystyrene equivalent value obtained by gel permeation chromatography.
(c3) The component (B) is a vinyl monomer having a branched alkyl ester group having 3 to 5 carbon atoms and having no alicyclic structure, and can be used without particular limitation. Examples of the component (c3) include: isopropyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, isoamyl (meth) acrylate, 2-methylbutyl (meth) acrylate, and the like.
(c4) The components are arbitrary components. Examples of the component (c4) include mono (meth) acrylates having a hydrocarbon group having less than 3 or 6 carbon atoms and vinyl monomers having an aromatic ring structure. Examples of the mono (meth) acrylates having a hydrocarbon group having less than 3 or 6 carbon atoms include: methyl (meth) acrylate, ethyl (meth) acrylate, hexyl (meth) acrylate, ethylhexyl (meth) acrylate, and the like. Examples of the aromatic ring structure vinyl monomers include: styrene, α -methylstyrene, 4-methylstyrene, benzyl (meth) acrylate, phenyl (meth) acrylate, and the like.
(C) Component (c) is obtained by radical copolymerization of component (c1), component (c2), component (c3) and, if necessary, component (c4) by various known methods. The reaction temperature for synthesizing the component (C) is usually about 40 to 160 ℃ and the reaction time is about 2 to 12 hours. Examples of the radical polymerization initiator in the copolymerization reaction include: inorganic peroxides, organic peroxides, azo compounds, and the like. Examples of the inorganic peroxide include: hydrogen peroxide, ammonium persulfate, potassium persulfate, and the like. Examples of the organic peroxide include: benzoyl peroxide, dicumyl peroxide, lauryl peroxide, and the like. Examples of the azo compound include 2, 2-azobis (isobutyronitrile), 2' -azobis (methylbutyronitrile), and the like. The amount of the radical polymerization initiator used in the copolymerization reaction is usually about 0.01 to 10% by mass based on the total mass of the components (c1) to (c 4). Chain transfer agents may also be used in the copolymerization reaction. Examples of the chain transfer agent include: lauryl mercaptan, dodecyl mercaptan, 2-mercaptobenzothiazole, bromotrichloromethane, and the like. The amount of the chain transfer agent used is usually about 0.01 to 10% by mass based on the total mass of the components (c1) to (c 4). In the case of copolymerization by solution polymerization, an organic solvent may be used. Examples of the organic solvent include: glycol ether solvent, alcohol solvent, ketone solvent, aromatic solvent, ester solvent, alkyl halide solvent, amide solvent, etc. Examples of the glycol ether solvent include ethylene glycol monoethyl ether and propylene glycol monomethyl ether. Examples of the alcohol solvent include: methanol, ethanol, n-propanol, and the like. Examples of the ketone solvent include: acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like. Examples of the aromatic solvent include: benzene, toluene, xylene, and the like. Examples of the ester solvent include ethyl acetate and butyl acetate. The alkyl halide solvent may, for example, be chloroform. Examples of the amide solvent include dimethylformamide. The organic solvent is preferably a glycol ether solvent in terms of the dissolving power of components (c1) to (c 4).
(c1) The copolymerization ratio (mass ratio) of the component (c2), the component (c3) and the component (c2) is not particularly limited, but is preferably 20 to 70: 20-40: 5-50, more preferably 40-55: 20-40: 10 to 30, more preferably 45 to 55: 25-35: 10 to 25. When the component (c4) is added, the copolymerization ratio (mass ratio) of the component (c1), the component (c2), the component (c3) and the component (c4) is preferably 20 to 70: 20-40: 5-50: 1 to 20, more preferably 40 to 55: 20-40: 10-30: 1 to 10, and more preferably 45 to 55: 25-35: 10-25: 1 to 10.
As for the physical properties of the component (C), for example, the limiting viscosity of a propylene glycol monomethyl ether dilute solution (1 to 2% by mass) of the component (C) at 25 ℃ is 0.05dl/g or more, specifically about 0.1 to 1 dl/g. When the limiting viscosity is 0.05dl/g or more, the antistatic property of the cured product is improved by making the component (C) less likely to bleed out onto the surface of the cured product of the active energy ray-curable resin composition.
Examples of the nonionic antistatic agent include: polyoxyethylene alkyl ethers, polyoxyethylene alkylphenol ethers, polyoxyethylene alkylamine/amides, sorbitan and the like.
Examples of alkali metals of the antistatic agent using an alkali metal salt include: lithium, sodium, potassium, and the like.
The substances exemplified as the component (C) and the substances known as the component (C) may be used alone or in combination of two or more. The component (C) is preferably a cationic antistatic agent, more preferably a quaternary ammonium salt, and even more preferably a polymer having a quaternary ammonium salt group, in view of good transparency of the cured product of the active energy ray-curable resin composition of the present invention and low cost.
(A) The upper limit of the content ratio (mass ratio, solid content conversion, [ (a) component/(C) component ]) of the component (C) may be 99/1, 98/2, 97/3, 96/4, 95/5, 94/6, 93/7, 92/8, 91/9, 90/10, 85/15, etc., and the lower limit may be 98/2, 97/3, 96/4, 95/5, 94/6, 93/7, 92/8, 91/9, 90/10, 85/15, 80/20, etc. In one embodiment, the content ratio of the component (a) to the component (C) (in terms of solid content, [ (a) component/(C) component ]) is preferably about 80/20 to 99/1 in order to exhibit the effects of the present invention satisfactorily.
(B) The upper limit of the content ratio (mass ratio, solid content conversion, [ (B) component/(C) component ]) of the component (C) may be 20/80, 15/85, 10/90, 9/91, 8/92, 7/93, 6/94, 5/95, 4/96, 3/97, 2/98, etc., and the lower limit may be 15/85, 10/90, 9/91, 8/92, 7/93, 6/94, 5/95, 4/96, 3/97, 2/98, 1/99, etc. In one embodiment, the content ratio of the component (B) to the component (C) (in terms of solid content, [ (B) component/(C) component ]) is preferably about 1/99 to 20/80 in order to exhibit the effects of the present invention satisfactorily.
(C) The upper limit of the content (in terms of solid content) of the component (a) in 100% by mass of all the constituent units of the component (B) and the component (C) in terms of solid content in the present invention may be 30% by mass, 25% by mass, 20% by mass, 15% by mass, 10% by mass, 5% by mass, 4% by mass, 3% by mass, etc., and the lower limit may be 25% by mass, 20% by mass, 15% by mass, 10% by mass, 5% by mass, 4% by mass, 3% by mass, 2% by mass, etc. In one embodiment, the content of the component (C) in 100% by mass of all the constitutional units of the components (a), (B), and (C) in terms of solid content in the present invention (in terms of solid content) is preferably about 2% by mass to 30% by mass, more preferably 2% by mass to 20% by mass, still more preferably 2% by mass to 15% by mass, and particularly preferably 2% by mass to 10% by mass. When the amount is not less than the lower limit, the effect as an antistatic agent can be sufficiently exhibited. When the content is not more than the upper limit, compatibility with other components becomes good, and the resin layer has excellent transparency.
< photopolymerization initiator (D) >
The active energy ray-curable resin composition of the present invention may contain a photopolymerization initiator (D) (also referred to as "component (D)" in the present invention). Examples of the photopolymerization initiator include: radical photopolymerization initiators, cationic photopolymerization initiators, and anionic photopolymerization initiators.
Examples of the radical photopolymerization initiator include: a phenylalkyl ketone type photopolymerization initiator, an acylphosphine oxide type photopolymerization initiator, a hydrogen abstraction type photopolymerization initiator, an oxime ester type photopolymerization initiator, and the like.
Examples of the phenylalkyl ketone photopolymerization initiator include: benzildimethyl ketals such as 2, 2-dimethoxy-1, 2-diphenylethane-1-one, α -hydroxybenzyl ketones such as 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one, and α -aminobenzyl ketones such as 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one.
Examples of the acylphosphine oxide type photopolymerization initiator include 2,4, 6-trimethylbenzoyl-diphenyl-phosphine oxide, bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide, and the like.
Examples of the hydrogen abstraction-type photopolymerization initiator include methyl phenylglyoxylate and the like.
Examples of the oxime ester type photopolymerization initiator include 1, 2-octanedione, 1- [4- (phenylthio) -,2- (O-benzoyloxime) ], ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acetyloxime), and the like.
Examples of the cationic photopolymerization initiator include: iodonium, (4-methylphenyl) [4- (2-methylpropyl) phenyl ] -hexafluorophosphate (1-), propylene carbonate, triarylsulfonium hexafluorophosphate, triarylsulfonium tetrakis- (pentafluorophenyl) borate, and the like.
Examples of the anionic photopolymerization initiator include: cobalamin complex, o-nitrobenzyl alcohol carbamate, oxime ester, and the like.
As the photopolymerization initiator, commercially available products can be used. As the product, there can be exemplified: 2, 2-dimethoxy-1, 2-diphenylethane-1-one (product name "Omnirad (hereinafter, also referred to as" ohmic nide ") 651", manufactured by IGM Resins Co., Ltd.), 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one (product name "ohmic nide 2959", manufactured by IGM Resins Co., Ltd.), 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one (product name "ohmic nide 127", manufactured by IGM Resins Co., Ltd.), 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one -1-ketone (product name "ohm Nrad 907", manufactured by IGM resins Co.), 2,4, 6-trimethylbenzoyl-diphenyl-phosphine oxide (product name "ohm Nrad TPO H", manufactured by IGM resins Co.), bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide (product name "ohm Nrad 819", manufactured by IGM resins Co.), methyl phenylglyoxylate (product name "ohm Nrad MBF", manufactured by IGM resins Co.), 1, 2-octanedione, 1- [4- (phenylthio) -,2- (O-benzoyloxime) ] (product name "Brilliant OXE 01", manufactured by BASF Japan) (Strand), ethanone, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -1- (O-acetyloxime) (product name "Brilliant OXE 02", manufactured by BASF corporation), iodonium, (4-methylphenyl) [4- (2-methylpropyl) phenyl ] -hexafluorophosphate (1-), and a mixture of propylene carbonate (product name "Omnicat (hereinafter, also referred to as" OnnyKatt ") 250", manufactured by IGM resins), triarylsulfonium hexafluorophosphate (product name "OnnyKatt 270", manufactured by IGM resins), triarylsulfonium tetrakis- (pentafluorophenyl) borate (product name "Brilliant Olgacure (IRGACURE) 290", manufactured by BASF corporation), and the like.
The photopolymerization initiator exemplified above and the photopolymerization initiator known in the art can be used alone or in combination of two or more. The photopolymerization initiator is preferably a radical photopolymerization initiator, more preferably a phenylalkyl ketone photopolymerization initiator, more preferably an alpha-aminophenylalkyl ketone and/or an alpha-hydroxyphenylalkyl ketone, more preferably, it is at least one selected from the group consisting of 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one, and 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one.
(D) Examples of the upper limit of the content (in terms of solid content) of the component (c) in 100% by mass of all the structural units in terms of solid content in the active energy ray-curable resin composition of the present invention include 20% by mass, 15% by mass, 10% by mass, 8% by mass, 6% by mass, 4% by mass, 2% by mass, 1% by mass, and 0.5% by mass, and examples of the lower limit thereof include 15% by mass, 10% by mass, 8% by mass, 6% by mass, 4% by mass, 2% by mass, 1% by mass, 0.5% by mass, and 0.1% by mass. In one embodiment, the content of the component (D) in 100 mass% of all the structural units in terms of solid content of the active energy ray-curable resin composition of the present invention (in terms of solid content) is preferably about 0.1 to 20 mass%.
Other Agents capable of formulation
In the active energy ray-curable resin composition of the present invention, various additives such as a binder resin, an anti-slip agent, a slip aid, an antiseptic agent, inorganic particles, a rust preventive, a pH adjuster, a pigment, a dye, a lubricant, a leveling agent, a catalyst, an antifoaming agent, and a photosensitizer (amines, quinones, etc.) may be further blended as necessary in addition to the above-mentioned components.
The active energy ray-curable resin composition of the present invention can be used by optionally blending a solvent (E) (also referred to as "component (E)" in the present invention) and adjusting the viscosity. Examples of the solvent include water and organic solvents. The organic solvent may be any of various known organic solvents. Examples of the organic solvent include: ketone solvent, aromatic solvent, alcohol solvent, glycol ether solvent, ester solvent, petroleum solvent, alkyl halide solvent, amide solvent, etc.
Examples of the ketone solvent include: methyl ethyl ketone, acetylacetone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, and the like.
Examples of the aromatic solvent include toluene and xylene.
Examples of the alcohol solvent include: methanol, ethanol, n-propanol, isopropanol, butanol, and the like.
Examples of the diol solvent include: ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, polyethylene glycol, polypropylene glycol, and the like.
Examples of the glycol ether solvent include: ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-isopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-isobutyl ether, ethylene glycol mono-t-butyl ether, and the like.
Examples of the ester solvent include: ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, and the like.
Examples of the petroleum solvent include aromatic oil (SOLVESSO) #100 (manufactured by Exxon) and aromatic oil (SOLVESSO) #150 (manufactured by Exxon).
The alkyl halide solvent may, for example, be chloroform.
Examples of the amide solvent include dimethylformamide.
The substances exemplified as the solvent and the substances known as the solvent may be used alone or in combination of two or more.
The upper limit of the content ratio of the solvent to the solid content of the active energy ray-curable resin composition of the present invention (mass ratio, [ active energy ray-curable resin composition/solvent of the present invention ]) may be 99/1, 95/5, 90/10, 80/20, 70/30, 60/40, 50/50, 40/60, 30/70, 20/80, 10/90, 5/95, etc., and the lower limit may be 95/5, 90/10, 80/20, 70/30, 60/40, 50/50, 40/60, 30/70, 20/80, 10/90, 5/95, 1/99, etc. In one embodiment, the content ratio (mass ratio, [ active energy ray-curable resin composition/solvent of the present invention ]) of the solvent to the solid content of the active energy ray-curable resin composition of the present invention is preferably about 1/99 to 99/1. By reducing the amount of the solvent, the film thickness of the resin layer of the present invention can be increased.
< method for producing active energy ray-curable resin composition >
The active energy ray-curable resin composition of the present invention can be obtained by mixing the component (a), the component (B), and if necessary, the component (C), the component (D), and the component (E) at normal temperature and pressure.
< laminate >
The present invention provides a laminate having a substrate and a resin layer. Further, the present invention provides a method for producing a laminate, comprising: curing the active energy ray-curable resin composition of the present invention applied to at least one surface of the substrate with an active energy ray. The cured product obtained in the manner described above is also referred to as a resin layer in the present invention.
Examples of the substrate to which the active energy ray-curable resin composition of the present invention is applied include: glass substrates, metal substrates, plastic substrates, and the like. Examples of the plastic substrate include a thermoplastic substrate, a thermosetting plastic substrate, and the like. Examples of the thermoplastic base material include general-purpose plastic base materials and engineering plastic base materials. Examples of the general-purpose plastic substrate include: olefinic, polyester, acrylic, vinyl, polystyrene, and the like. Examples of the olefin system include: polyethylene, polypropylene, norbornene, and the like. Examples of the polyester include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and the like. As the acrylic, polymethyl methacrylate (PMMA) and the like can be exemplified. Examples of the vinyl system include: polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, and the like. Examples of polystyrenes include: polystyrene (PS) resin, styrene-Acrylonitrile (AS) resin, styrene-butadiene-Acrylonitrile (ABS) resin, and the like. Examples of the engineering plastic substrate include general-purpose engineering plastics and super engineering plastics. Examples of the general-purpose engineering plastic include polycarbonate, polyamide (nylon), and the like. Examples of the super engineering plastic include Polyetheretherketone (PEEK). Examples of the thermosetting plastic substrate include: polyimide, epoxy, melamine, and the like. As another plastic substrate, triacetyl cellulose resin and the like can be exemplified. The plastic substrate may be a copolymer of the plurality of plastics. The substrate of the present invention may be a multilayer comprising a plurality of said substrates. In addition, the substrate may be a substrate subjected to surface treatment (corona discharge or the like). Further, another layer (for example, an easy-to-adhere layer, an anchor layer, or the like) may be provided on one surface or both surfaces of the substrate between the active energy ray-curable resin composition of the present invention and the layer. The base material is preferably a polyester-based film, and more preferably a polyethylene terephthalate film, which is excellent in transparency, dimensional stability, mechanical properties, chemical resistance, and the like. The substrate is preferably polyimide, which is excellent in heat resistance, dimensional stability, mechanical properties, and the like. The upper limit of the thickness of the substrate may be 300. mu.m, 275. mu.m, 250. mu.m, 225. mu.m, 200. mu.m, 175. mu.m, 150. mu.m, 125. mu.m, 100. mu.m, 75. mu.m, 50. mu.m, 25. mu.m, 10. mu.m, etc., and the lower limit may be 275. mu.m, 250. mu.m, 225. mu.m, 200. mu.m, 175. mu.m, 150. mu.m, 125. mu.m, 100. mu.m, 75. mu.m, 50. mu.m, 25. mu.m, 10. mu.m, 1. mu.m, etc. In one embodiment, the thickness of the substrate is preferably 1 μm to 300. mu.m, more preferably 25 μm to 250. mu.m, even more preferably 50 μm to 200. mu.m, particularly preferably 50 μm to 150. mu.m, even more preferably 75 μm to 125. mu.m.
Examples of the method for applying the active energy ray-curable resin composition of the present invention to a substrate include: roll coater coating, reverse roll coater coating, rod coater coating, meyer bar coating, air knife coating, gravure coating, reverse gravure coating, offset printing, flexographic printing, screen printing, and the like. The coating amount is not particularly limited, and is usually 0.01g/m in mass after drying2～20g/m2Preferably in the range of 0.025g/m2～10g/m2More preferably 0.05g/m2～5g/m2. The upper limit of the thickness of the resin layer may be, for example, 50 μm, 45 μm, 40 μm, 35 μm, 30 μm, 25 μm, 20 μm, 15 μm, 10 μm, 5 μm, 4 μm, 3 μm, 2 μm, 1 μm, 0.5 μm, 0.1 μm, 0.05 μm, etc., and the lower limit may be, for example, 45 μm, 40 μm, 35 μm, 30 μm, 25 μm, 20 μm, 15 μm, 10 μm, 5 μm, 4 μm, 3 μm, 2 μm, 1 μm, 0.5 μm, 0.1 μm, 0.05 μm, 0.01 μm, etc. The thickness of the resin layer is preferably 0.01 to 50 μm, more preferably 0.05 to 25 μm, still more preferably 0.1 to 10 μm, particularly preferably 0.5 to 10 μm, and still more preferably 1 to 5 μm.
Examples of the method of curing by irradiation with active energy rays include irradiation with 10mJ/cm light using a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a carbon arc lamp, a metal halide lamp, a xenon lamp, a chemical lamp, an electrodeless discharge lamp, a Light Emitting Diode (LED) or the like that emits light in a wavelength region of 150nm to 450nm, and the like2Above and 10,000mJ/cm2The following methods are used. Before the irradiation with the active energy ray, the material may be dried by heating as necessary. After the irradiation with the active energy ray, the cured product may be heated as necessary to be completely cured. The heating conditions include about 60 to 150 ℃ and 30 secondsAbout 30 minutes, preferably about 70 to 130 ℃ and about 50 seconds to 10 minutes.
The active energy ray-curable resin composition of the present invention is considered to be used as in the following (1) to (12). The active energy ray-curable resin composition of the present invention is preferably used as a hard coat layer, but it is also possible to use the active energy ray-curable resin composition of the present invention for various applications such as the effects of the active energy ray-curable resin composition of the present invention.
(1) The cured product and the substrate of the active energy ray-curable resin composition of the present invention
(2) The cured product of the active energy ray-curable resin composition of the present invention, the primer layer, and the substrate
(3) The cured product of the active energy ray-curable resin composition of the present invention, a substrate, and an adhesive layer
(4) The cured product of the active energy ray-curable resin composition of the present invention, the primer layer, the substrate, and the adhesive layer
(5) Antifouling layer, cured product of active energy ray-curable resin composition of the invention, and substrate
(6) Antifouling layer, cured product of active energy ray-curable resin composition of the present invention, primer layer, and substrate
(7) Antifouling layer, cured product of active energy ray-curable resin composition of the invention, base material, and adhesive layer
(8) Antifouling layer, cured product of active energy ray-curable resin composition of the present invention, primer layer, base material, and adhesive layer
(9) Low refractive index layer, high refractive index layer, cured product of active energy ray-curable resin composition of the present invention, and substrate
(10) Low refractive index layer, high refractive index layer, cured product of active energy ray-curable resin composition of the present invention, substrate, and adhesive layer
(11) Low refractive index layer, high refractive index layer, cured product of active energy ray-curable resin composition of the present invention, primer layer, and substrate
(12) Low refractive index layer, high refractive index layer, cured product of active energy ray-curable resin composition of the present invention, primer layer, substrate, and adhesive layer
The resin layer of the laminate of the present invention satisfies condition 1 and condition 2.
Condition 1 is the press-in hardness (N/mm) of the resin layer of the laminate2) Is 450 or more and 600 or less. Indentation hardness (N/mm) of resin layer of laminate2) The numerical value corresponds to the hardness of the resin layer of the laminate. Indentation hardness (N/mm) of resin layer of laminate2) Examples of the upper limit of (b) may include 600, 575, 550, 525, 500, 475, etc., and examples of the lower limit of (b) may include 575, 550, 525, 500, 475, 450, etc. In one embodiment, the press-in hardness (N/mm) of the resin layer of the laminate2) Preferably 450 to 600. By setting the upper limit or less, the hardness of the laminate can be appropriately maintained, and therefore a laminate having flexibility can be obtained. When the lower limit or more is set, the laminate can have a hard coat property. That is, in order to achieve both a certain flexibility and a certain hard coat performance, it is important that the above range is satisfied.
Condition 2 is that the elongation at break of the resin layer of the laminate is 3.7% or more and 10.0% or less. The elongation at break of the resin layer of the laminate is a value corresponding to the hardness of the resin layer. Examples of the upper limit of the elongation at break (%) of the resin layer of the laminate include 10.0, 9.0, 8.0, 7.0, 6.0, 5.0, 4.0, 3.9 and 3.8, and examples of the lower limit thereof include 9.0, 8.0, 7.0, 6.0, 5.0, 4.0, 3.9, 3.8 and 3.7. In one embodiment, the resin layer of the laminate preferably has an elongation at break (%) of 3.7 to 10.0. When the amount is not more than the upper limit, the resin layer of the laminate can be suppressed from becoming too soft, and the hard coatability can be maintained. By being equal to or more than the lower limit, the resin layer of the laminate can have flexibility. That is, in order to achieve both a certain flexibility and a certain hard coat performance, it is important that the above range is satisfied. The elongation at break in condition 2 is a ratio of a length (cm) extending from a length (cm) of the laminate of 0% when the state before the laminate is stretched is 0%. Specifically, a commercially available tensile tester such as Tensilon universal tester (product name "RTG-1250", manufactured by Anden (A & D) Inc.) is used to stretch a sample in the longitudinal direction thereof at a speed of 10mm/min at normal temperature, and the length of the sample before stretching and the length of the sample when a crack is found on the sample are used to calculate the tensile strength from the following formula.
Elongation at break (%) < 100X (L-Lo)/Lo
Lo: length of specimen before stretching
L: length of specimen at the time of initial crack detection
[ examples ]
Specific examples of the present invention will be described below with reference to examples, but the present invention is not limited to these examples. In the examples, unless otherwise specified, parts and% are based on the mass of the solid content.
(c2) The weight average molecular weight of the component (a) is an actual value measured under the following conditions by a commercially available molecular weight measuring instrument described below.
Molecular weight measuring machine: the product is "HLC-8220 GPC", manufactured by Tosoh
Pipe column: the products are TSKGel G6000PWXL-CP and TSKGel G3000PWXL-CP, all manufactured by Tosoh
Developing solvent: 0.1M NaNO3And 0.1M acetic acid solution
Flow rate: 0.5mL/min
Sample concentration: 0.5g/L
< Synthesis examples 1-1: synthesis of (meth) acrylic ester (A-1)
In a 300mL four-necked flask equipped with a stirrer, a thermometer, a cooler and a dry gas introduction tube, 310 parts of isophorone diisocyanate (also referred to as "ipdi (isophoron diisocyanate)" in the present invention), 690 parts of pentaerythritol tri/tetraacrylate (manufactured by "arix M305" in the trade name "manufactured by toya synthesis (PETA terthrite/tetraacrylate)") and 0.6 parts of tin octylate were charged, and then the temperature in the system was raised to about 80 ℃ over about 1 hour. Then, after the reaction system was kept at the temperature for 2 hours, cooling was performed to obtain urethane acrylate (A-1).
< Synthesis examples 1-2 to 1-5 and comparative Synthesis examples 1-1 to 1-3: synthesis of Poly (meth) acrylates (A-2) to Poly (meth) acrylates (A-5) and Poly (meth) acrylates (A-C1) to Poly (meth) acrylates (A-C3) >
Synthesis examples 1-2 to 1-5 and comparative Synthesis examples 1-1 to 1-3 (meth) acrylic esters (A-2) to (meth) acrylic esters (A-5) and (meth) acrylic esters (A-C1) to (meth) acrylic esters (A-C3) were obtained in the same manner as in Synthesis example 1-1, except that the compositions shown in Table 1 were changed.
[ Table 1]
| (A-1) | (A-2) | (A-3) | (A-4) | (A-5) | (A-C1) | (A-C2) | (A-C3) | |
| IPDI | 310 | |||||||
| HDInu | 277 | 109 | ||||||
| HDIad | 267 | |||||||
| HDIbi | 265 | 606 | 104 | |||||
| HDI | 254 | |||||||
| PETA | 690 | 723 | 733 | 735 | 746 | |||
| HEA | 394 | |||||||
| DPPA | 891 | 896 |
The terms in Table 1 have the following meanings.
IPDI: isophorone diisocyanate (manufactured by Tokyo chemical industry)
HDlnu: uroacetate of hexamethylene diisocyanate (product name "Crosstide (HXR)", manufactured by Tosoh)
HDIad: adduct of hexamethylene diisocyanate (product name "Crosstide (Konate) HL", manufactured by Tosoh)
HDIbi: biuret of hexamethylene diisocyanate (product name "Desmodur (Desmodur) N3200", manufactured by Covestro AG)
HDI: hexamethylene diisocyanate (product name "Crohn Add (Coronate) HDI", manufactured by Tosoh Corona)
PETA: pentaerythritol tri/tetraacrylate (product name "Aronix M305", manufactured by Toyo Seiya synthesis (stock))
HEA: hydroxyethyl acrylate (manufactured by Osaka organic chemical industry (Strand))
DPPA: dipentaerythritol penta/hexaacrylate (product name "Aronix M400", manufactured by Toyo Seiya Kabushiki Kaisha)
< Synthesis example 2-1: synthesis of antistatic agent (C-1)
130 parts of hydroxyethyl methacrylate, 1140 parts of epsilon-caprolactone and 1.3 parts of tin octylate were charged into a reaction apparatus equipped with a stirring apparatus and a cooling tube, and the mixture was heated to 150 ℃ and kept warm for 6 hours and then cooled to obtain a monofunctional vinyl monomer having a polyester structure and a weight average molecular weight of 5500 (hereinafter, also referred to as "component c 2-1"). 100 parts of methacryloyloxyethyltrimethyl ammonium chloride (DMC) (hereinafter, also referred to as a "component (c 1-1)"), 60 parts of a component (c2-1) ", 40 parts of isopropyl methacrylate (hereinafter, also referred to as a" component (c3-1) "), and 800 parts of Propylene Glycol Monomethyl Ether (PGME) were charged into a reaction apparatus including a stirring apparatus and a cooling tube, and the temperature was increased to 90 ℃. Then, 8 parts of 2,2'-azobis (methylbutyronitrile) (2,2' -azobis (methyl butyronitride), AMBN) and 32 parts of PGME were added to start the polymerization, and the mixture was kept at 100 ℃ for 6 hours and then cooled to obtain a solution (nonvolatile content: 20%) of the polymer (C-1) having a quaternary ammonium salt structure.
< example 1: preparation of active energy ray-curable resin composition (1)
Into a 300mL four-necked flask equipped with a stirrer, a thermometer, a cooler and a dry gas introduction tube, 50 parts of urethane acrylate (a-1), 50 parts of PETA, 5 parts of 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one (product name "ohmic charader (Omnirad) 2959", manufactured by IGM corporation) as a photopolymerization initiator, and 0.5 part of component (B) (product name "meifa (Megafac) RS-90") as a compound having a fluorine atom and a polymerizable unsaturated group were blended in a solid content ratio and diluted with PGME to prepare an active energy ray-curable resin composition (1) having a nonvolatile content of 30%.
< example 2 to example 5: preparation of active energy ray-curable resin compositions (2) to (5)
Examples 2 to 5 were carried out in the same manner as in example 1 except that the compositions shown in table 2 were changed to obtain active energy ray-curable resin compositions (2) to (5).
< example 6: preparation of active energy ray-curable resin composition (6)
Into a 300mL four-necked flask equipped with a stirrer, a thermometer, a cooler and a dry gas inlet tube, 50 parts of urethane acrylate (A-1), 50 parts of PETA, 5 parts of 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one (product name "Omnirad) 2959", manufactured by IGM resin Co., Ltd.) as a photopolymerization initiator, 5 parts of polymer (C-1) containing a quaternary ammonium salt structure as an antistatic agent, and 0.5 part of component (B) which is a compound having a fluorine atom and a polymerizable unsaturated group (product name "Meigafac (Megafac) RS-90") were blended in a solid content ratio and diluted with PGME, thus, an active energy ray-curable resin composition (6) having a nonvolatile content of 30% was prepared.
< example 7 to example 10 and comparative examples 1 to 10: preparation of active energy ray-curable resin compositions (7) to (10) and active energy ray-curable resin compositions (C1) to (C10)
Examples 7 to 10 and comparative examples 1 to 10 were prepared in the same manner as in example 6 except that the compositions shown in tables 2 and 3 were changed to obtain active energy ray-curable resin compositions (7) to (10) and active energy ray-curable resin compositions (C1) to (C10).
< evaluation example 1: production of laminate (1)
An active energy ray-curable resin composition (1) was applied to a 100 μm-thick PET film (COSMOSHINE) a4100 manufactured by tokyo corporation) by a bar coater #10 so that the film thickness of the cured film was 3 μm, and dried at 80 ℃ for 1 minute to prepare a film. Then, the obtained film was subjected to UV curing using a high pressure mercury lamp 300mJ/cm (manufactured by Ubber corporation, product name: UBT-080-7A/BM)2) Thereby obtaining a laminate (1).
< evaluation example 2 to evaluation example 10 and comparative evaluation example 1 to comparative evaluation example 10: production of laminates (2) to (10) and laminates (C1) to (C10)
Evaluation examples 2 to 10 and comparative evaluation examples 1 to 10 laminates (2) to (10) and laminates (C1) to (C10) were obtained in the same manner as in evaluation example 1, except that the active energy ray-curable resin composition (1) was changed to the active energy ray-curable resin compositions (2) to (10) or the active energy ray-curable resin compositions (C1) to (C10), respectively.
< evaluation of Properties (1): indentation hardness (N/mm)2)＞
The indenter was pressed against the surface of the resin layer of the laminate, and the indentation hardness was calculated from the obtained load displacement curve. As the indenter tip correction method, a field method is applied. As a load-removing fitting method, a straight line approximation is performed from the upper 65% to 100% to set a tangent line.
A measuring device: ultra-micro indentation hardness tester ENT-2100 manufactured by Elliox (Elionix) GmbH
Pressure head: pyramid pressure head Berkovich (Berkovich)
Maximum load: 1.0mN
Load increase speed: 1.0mN/10 sec
Hold time at maximum load: 5 seconds
Load removal rate: 1.0mN/10 sec
Measuring ambient air temperature: 30 deg.C
Measuring the humidity of the environment: 50 percent of
< evaluation of Properties (2): elongation at break >
The elongation at break of the laminate was evaluated on a sample cut out in a long shape of 1cm in length and 10cm in width.
A measuring device: tencilon universal tester (product name "RTG-1250", manufactured by Aiander (A & D) (stock))
Stretching speed: 10mm/min
A load meter: 100N
The test times are as follows: 5 times (twice)
Distance between chucks: 50mm
Measuring ambient air temperature: 23 deg.C
Measuring the humidity of the environment: 50 percent of
< evaluation of Performance (3): steel wool resistance test
For the resin layer surface of the laminate, the thickness was measured according to JIS K7136: the haze value was measured using a color haze meter 2000. Then, Steel Wool #0000 (product name "Bonstar) B-204", manufactured by Japan Steel Wool (Strand) was used at 500g/cm on the surface of the resin layer of the laminate2After 500 times of back-and-forth rubbing under the conditions of load, speed 100mm/sec and moving distance 30mm, the composition was further measured according to JIS K7136: the haze value was measured using a color haze meter 2000. The difference in haze value between before and after rubbing with steel wool was evaluated according to the following criteria.
AAA: less than 0.15
AA: 0.15 or more and less than 0.20
A: 0.20 or more and less than 0.30
B: 0.30 or more
< evaluation of Performance (4): mandrel test >
According to the mandrel test described in JIS-K5600-5-1 (test in which samples were wound around stainless steel cylinders having diameters of 2mm, 3mm, 4mm, 5mm, 6mm, 8mm, 10mm, 12mm, 16mm, 20mm, 25mm, and 32 mm), when the laminate was wound around the stainless steel cylinder with the resin layer positioned outside, the minimum diameter of the cylinder in which no crack (crack) occurred in the resin layer was measured, and the evaluation was performed according to the following criteria.
AA: minimum diameter of 4mm or less
A: minimum diameter of 5mm
B: minimum diameter of 6mm or more
< evaluation of Properties (5): abrasion resistance test
A rubber (product name "military rubber stick", manufactured by minoen (Minoan)) was used as a head of a friction tester, pressed vertically from above to the surface of the resin layer of the laminate with a load of 1000g, rubbed reciprocally 1000 times at a stroke length of 2.0cm and a rubbing speed of 60rpm, and then the attached rubber was removed, and then a water contact angle was measured and evaluated according to the following criteria. The water contact angle was measured as follows. The water contact angle at 23 ℃ and 50% relative humidity of the resin layer of the laminate after rubbing with a rubber was measured by a liquid Drop method in which 2.0. mu.L of a water Drop was dropped and measured 1000ms after dropping the water Drop by a theta/2 method using a contact angle measuring apparatus (product name "Drop Master DM-300", manufactured by Kyowa Kagaku Kogyo Co., Ltd.).
AAA: the contact angle of water exceeds 106 °
AA: the contact angle of water is more than 104 DEG and less than 106 DEG
A: the contact angle of water is more than 103 DEG and not more than 104 DEG
B: the contact angle of water is less than 103 DEG
[ Table 2]
[ Table 3]
The meanings of the terms in tables 2 and 3 are as follows.
ATM-4E: EO-modified pentaerythritol tetra (meth) acrylate (product name "NK ester (NK ester) ATM-4E", manufactured by Xinzhongcun chemical industry (stock))
DPCA-30: caprolactone-modified dipentaerythritol hexa (meth) acrylate (product name "Kayarad (KAYARAD) DPCA-30", manufactured by Japan Chemicals (K.K.))
DPH-12E: ethoxylated dipentaerythritol hexaacrylate (product name "A-DPH-12E", manufactured by Xinzhongcun chemical industry (stock))
Photopolymerization initiator: 1- [4- (2-hydroxyethoxy) -phenyl ] -2-hydroxy-2-methyl-1-propan-1-one (product name "Omnirad) 2959", manufactured by IGM resins Co., Ltd.)
Claims (7)
1. An active energy ray-curable resin composition constituting a resin layer in a laminate having a substrate and a resin layer, the active energy ray-curable resin composition comprising:
(meth) acrylic acid ester (A), and
a compound (B) having a fluorine atom, and
the following conditions 1 and 2 are satisfied;
condition 1: the press-in hardness of the resin layer was 450N/mm2Above and 600N/mm2The following;
condition 2: the elongation at break of the resin layer is 3.7% or more and 10.0% or less.
2. The active energy ray-curable resin composition according to claim 1, wherein the (A) component comprises a urethane (meth) acrylate (a1) and/or a hydroxyl group-containing (meth) acrylate (a 2).
3. The active energy ray-curable resin composition according to claim 2, wherein the component (a1) is a reaction product of a polyisocyanate (a1-1) and a hydroxyl group-containing (meth) acrylate (a1-2), and the mass ratio of the component (a1-1) to the component (a1-2) (a1-1)/(a1-2) is 15/85 to 50/50.
4. The active energy ray-curable resin composition according to any one of claims 1 to 3, wherein the component (B) is a compound having a fluorine atom and a polymerizable unsaturated group.
5. The active energy ray-curable resin composition according to any one of claims 1 to 4, comprising an antistatic agent (C).
6. The active energy ray-curable resin composition according to any one of claims 1 to 5, wherein the (C) component is a polymer having a quaternary ammonium salt group.
7. A laminate comprising a substrate and a resin layer, wherein the resin layer is a cured product of the active energy ray-curable resin composition according to any one of claims 1 to 6.
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