CN115612382A - Active energy ray-curable resin composition, cured product, and optical sheet - Google Patents
Active energy ray-curable resin composition, cured product, and optical sheet Download PDFInfo
- Publication number
- CN115612382A CN115612382A CN202210794541.0A CN202210794541A CN115612382A CN 115612382 A CN115612382 A CN 115612382A CN 202210794541 A CN202210794541 A CN 202210794541A CN 115612382 A CN115612382 A CN 115612382A
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- CN
- China
- Prior art keywords
- active energy
- energy ray
- polymerizable compound
- resin composition
- curable resin
- Prior art date
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- GSJNBCZKEUYYLK-UHFFFAOYSA-N [phenoxy(phenyl)methyl] prop-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)C=C)OC1=CC=CC=C1 GSJNBCZKEUYYLK-UHFFFAOYSA-N 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- IJVHTTITHMXYTG-UHFFFAOYSA-N benzhydryl prop-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)C=C)C1=CC=CC=C1 IJVHTTITHMXYTG-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- UYYOUWIRVXKLMP-UHFFFAOYSA-N ethyl 2-[n-(2-ethoxy-2-oxoethyl)-2-(1,3,5-triazin-2-yl)-3,5-bis(trichloromethyl)anilino]acetate Chemical compound CCOC(=O)CN(CC(=O)OCC)C1=CC(C(Cl)(Cl)Cl)=CC(C(Cl)(Cl)Cl)=C1C1=NC=NC=N1 UYYOUWIRVXKLMP-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PZDUWXKXFAIFOR-UHFFFAOYSA-N hexadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C=C PZDUWXKXFAIFOR-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 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
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical class CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction 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
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000007964 xanthones Chemical class 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/47—Levelling agents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
Abstract
The invention provides an active energy ray-curable resin composition, a cured product and an optical sheet, which have high refractive index, high abrasion resistance and high self-healing property and can inhibit the adhesion of water. The active energy ray-curable resin composition is an active energy ray-curable resin composition containing a polymerizable compound (A), a photopolymerization initiator (B) and a leveling agent (C), and is characterized in that the polymerizable compound (A) contains a polymerizable compound (A1) having an alkylene oxide chain in the structure and a polymerizable compound (A2) having an SP value of 8.88 or less, and the polymerizable compound (A1) is contained so that the content of the alkylene oxide chain in the compound structure becomes 0.6mmol/g or more in the total amount of the composition.
Description
The present application claims priority based on japanese patent application No. 2021-116981 filed in japan on 7/15/2021, and the contents thereof are incorporated herein.
Technical Field
The present invention relates to an active energy ray-curable resin composition for optical articles, a cured product obtained by curing the composition, and an optical sheet containing the cured product.
Background
In recent years, with rapid development of display technologies of liquid crystal display devices and the like, demands for sheet-like or film-like optical members used for these devices have been increasing for new functions, high quality, and the like. As an example of such an optical member, there is a prism sheet used as a light-collecting film for a backlight.
The prism sheet refracts backlight light by the fine concave-convex structure on the surface, thereby improving the brightness of the front surface of the display. In recent years, prism sheets are required to have a high refractive index for further improving the brightness of displays and to have excellent abrasion resistance and self-healing properties.
For example, patent document 1 discloses an active energy ray-curable resin composition for optical articles, which contains a fluorene-based (meth) acrylate and phenoxybenzyl acrylate, and discloses that a cured product obtained by curing the composition has a high refractive index, is excellent in scratch resistance, and has appropriate self-healing properties.
Patent document 2 discloses a resin composition for optical materials, which contains a reaction product of a bisphenol a type epoxy resin and acrylic acid, a specific monofunctional to difunctional chain (meth) acrylate compound such as phenylphenoxyalkyl (meth) acrylate, and a photopolymerization initiator, and which is excellent in refractive index, hardness, recovery properties, and the like.
[ Prior art documents ]
[ patent document ]
[ patent document 1] International publication No. 2018/070256
[ patent document 2] Japanese patent laid-open No. 2012-219205
Disclosure of Invention
[ problems to be solved by the invention ]
Recently, in order to improve not only the high refractive index, abrasion resistance (scratch resistance), and self-healing property as described above but also durability expected to be used under various environments, a function of imparting water repellency to a prism sheet has been demanded. In the conventional prism sheet which does not exhibit hydrophobicity, moisture is likely to adhere to the surface of the prism sheet due to a temperature change during transportation or end use, and water stains are generated after the droplets are dried, which may result in a reduction in yield or a reduction in functionality of the prism sheet.
The present invention addresses the problem of providing an optical sheet and a cured product that have a high refractive index, high abrasion resistance, and high self-healing properties, and that can inhibit the adhesion of moisture by exhibiting a water contact angle, and an active energy ray-curable resin composition that can be used for these.
[ means for solving problems ]
Namely, the present invention provides the following inventions.
(1) An active energy ray-curable resin composition comprising a polymerizable compound (A), a photopolymerization initiator (B) and a leveling agent (C), wherein the polymerizable compound (A) comprises a polymerizable compound (A1) having an alkylene oxide chain in the structure and a polymerizable compound (A2) having an SP value of 8.88 or less, and the polymerizable compound (A1) is contained so that the content of the alkylene oxide chain in the structure of the compound is 0.6mmol/g or more based on the total amount of the composition.
(2) The active energy ray-curable resin composition according to (1), wherein the polymerizable compound (A2) contains a compound represented by the following formula (A2-1).
[ solution 1]
(wherein R is 21 Is a hydrogen atom or a methyl group, Q 21 Is a single bond or a divalent linking group, R 22 Is an alkyl group having 14 to 22 carbon atoms)
(3) The active energy ray-curable resin composition according to (1) or (2), wherein the polymerizable compound (A1) contains a compound represented by the following formula (A1-1).
[ solution 2]
(wherein R is 1 And R 2 Each independently represents a hydrogen atom or a methyl group, X 1 And X 2 Independently represents an alkylene group having 2 or 3 carbon atoms, m and n independently represent an integer of 1 or more, and m + n is 20 or more. )
(4) The active energy ray-curable resin composition according to any one of (1) to (3), wherein the polymerizable compound (A1) contains a compound represented by the following formula (A1-2).
[ solution 3]
(wherein R is 11 Represents a hydrogen atom or a methyl group, X 12 Represents an alkylene group having 2 or 3 carbon atoms, and p represents an integer of 1 or more. )
(5) The active energy ray-curable resin composition according to any one of (1) to (4), wherein the proportion of the polymerizable compound (A2) in the active energy ray-polymerizable compound (A) is 0.1 to 30% by mass.
(6) The active energy ray-curable resin composition according to any one of (1) to (5), wherein the proportion of the polymerizable compound (A1) in the active energy ray-polymerizable compound (A) is 30 to 95% by mass.
(7) A cured product of the active energy ray-curable resin composition according to any one of (1) to (6), wherein the refractive index is 1.54 or more.
(8) An optical sheet having a layer containing a cured product according to (7).
[ Effect of the invention ]
The cured product and the optical sheet obtained by curing the active energy ray-curable resin composition of the present invention can satisfy not only high refractive index, high abrasion resistance and appropriate self-healing properties, which are conventionally required characteristics, but also a good water contact angle, by using a polymerizable compound having an alkylene oxide chain in a structure in an amount of at least a certain amount, a hydrophobic polymerizable compound having an SP value of at most a certain amount, a photopolymerization initiator, and a leveling agent in combination. Therefore, the active energy ray-curable resin composition of the present invention can be suitably used for various optical article applications, for example, various optical sheets such as a prism sheet used for a display such as a liquid crystal display device, a lenticular sheet used for a stereograph, a projection screen, and the like, a fresnel lens sheet used for a condenser lens (condenser lens) of an overhead projector (overhead projector), and a diffraction grating used for a color filter, and the like.
Detailed Description
< active energy ray-polymerizable Compound >
The active energy ray-curable resin composition (hereinafter, may be simply referred to as "composition") of the present invention contains a polymerizable compound (a), a photopolymerization initiator (B), and a leveling agent (C).
[ polymerizable Compound (A) ]
The polymerizable compound (a) (hereinafter, sometimes referred to as "component (a)" or "compound (a)") includes a polymerizable compound (A1) having an alkylene oxide chain in the structure and a polymerizable compound (A2) having an SP value of 8.88 or less.
(polymerizable Compound (A1))
The polymerizable compound (A1) (hereinafter, may be referred to as "component (A1)" or "compound (A1)") is a compound having an alkylene oxide chain in the structure. When the compound (A1) has a certain amount or more of an alkylene oxide chain, the abrasion resistance and self-healing property of the cured composition are improved.
As the alkylene oxide chain, as long as it has "-O- (CH) 2 ) p The structure (p is an integer of 1 to 10, preferably an integer of 2 to 5) is not particularly limited, but an ethylene oxide chain, a propylene oxide chain, an epoxy Ding Wanlian, or a combination thereof is preferable, an ethylene oxide chain, a propylene oxide chain, or a combination thereof is more preferable, and a combination thereof is particularly preferableAn ethylene oxide chain is selected.
(A1) The component (A) is a polymerizable compound and has a polymerizable group polymerizable by an active energy ray in its structure. Examples of the polymerizable group include: (meth) acryloyl groups, (meth) acrylamide groups, vinyl ether groups, vinyl ester groups, maleimide groups, epoxy groups, and the like. In the present specification, "(meth) acryloyl group" and "(meth) acrylamide group" are generic terms including an acryloyl group and a methacryloyl group, and an acrylamide group and a methacrylamide group, respectively. The "(meth) acrylate" is a generic term including acrylate and methacrylate, respectively.
Among these, the polymerizable group is particularly preferably a (meth) acryloyl group because of high reactivity upon irradiation with an active energy ray.
Examples of the component (A1) include: alkylene oxide group-modified poly (meth) acrylate obtained by reacting polyhydric alcohol having an alkylene oxide group such as ethylene oxide-modified poly (meth) acrylate of trimethylolpropane, propylene oxide-modified poly (meth) acrylate of trimethylolpropane, ethylene oxide-modified poly (meth) acrylate of ditrimethylolpropane, propylene oxide-modified poly (meth) acrylate of ditrimethylolpropane, ethylene oxide-modified poly (meth) acrylate of pentaerythritol, propylene oxide-modified poly (meth) acrylate of pentaerythritol, ethylene oxide-modified poly (meth) acrylate of dipentaerythritol, ethylene oxide-modified poly (meth) acrylate of tetramethylolmethane, etc.; alkylene oxide-modified poly (meth) acrylate oligomers such as ethylene oxide-modified epoxy poly (meth) acrylate, propylene oxide-modified epoxy poly (meth) acrylate, ethylene oxide-modified urethane poly (meth) acrylate, propylene oxide-modified urethane poly (meth) acrylate, ethylene oxide-modified polyester poly (meth) acrylate, and propylene oxide-modified polyester poly (meth) acrylate; a di (meth) acrylate of an ethylene oxide adduct of bisphenol A, a di (meth) acrylate of a propylene oxide adduct of bisphenol A, a di (meth) acrylate of an ethylene oxide adduct of bisphenol F, a di (meth) acrylate of a propylene oxide adduct of bisphenol F, and the like.
Further, preferable compounds of the component (A1) include compounds represented by the following formula (A1-1).
[ solution 4]
In the formula, R 1 And R 2 Independently of one another, represent a hydrogen atom or a methyl group, preferably at least one hydrogen atom. So-called R 1 And R 2 They may be the same group or different groups.
X 1 And X 2 Independently represent an alkylene group having 2 or 3 carbon atoms. In the case where the number of carbon atoms is 2, the moiety is an ethylene oxide chain, and in the case where the number of carbon atoms is 3, the moiety is a propylene oxide chain. X 1 And X 2 The groups may be the same or different.
m and n independently represent an integer of 1 or more, and m + n is 20 or more. By setting m + n to 20 or more, excellent wear resistance and self-healing properties can be achieved. m + n is preferably 20 to 30, more preferably 20 to 25.
When m or n is 2 or more, plural X' s 1 Or X 2 Each of which may be the same or different, and from the viewpoint of ease of synthesis, a plurality of X's are preferred 1 Or X 2 Are each the same, particularly preferably all X 1 And X 2 The same is true.
Further, as the component (A1), a compound represented by the following formula (A1-2) is also preferable.
[ solution 5]
In the formula, R 11 Represents a hydrogen atom or a methyl group, preferably a hydrogen atom.
X 12 Represents an alkylene group having 2 or 3 carbon atoms, and is preferably an ethylene group having 2 carbon atoms. p represents an integer of 1 or more, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, further preferably 1 or 2,
when p is 2 or more, plural X' s 12 X's may be the same or different 12 Preferably all the same.
The compound represented by the formula (a 1-2) has a biphenyl structure, and thus contributes to increase in refractive index of a cured product obtained by curing the composition.
In the composition of the present invention, the component (A1) is contained in such a manner that the content of the alkylene oxide chain in the structure of the compound is 0.6mmol/g or more based on the total amount of the composition. The content of the alkylene oxide chain is preferably 0.6 to 1.6mmol/g, more preferably 0.6 to 1.2mmol/g, and still more preferably 0.6 to 1.0mmol/g. When the concentration is 0.6mmol/g or more, good self-healing properties can be obtained, and when the concentration is not more than the upper limit, a water contact angle can be expressed.
(A1) The content of the component itself is not particularly limited as long as the content of the alkylene oxide chain is satisfied, but is preferably 10 to 98% by mass, more preferably 10 to 55% by mass, further preferably 10 to 45% by mass, and particularly preferably 20 to 35% by mass of the total amount of the composition.
The content of the component (A1) is preferably 30 to 99.9% by mass, more preferably 60 to 98% by mass, even more preferably 70 to 98% by mass, and particularly preferably 80 to 95% by mass of the component (a).
(polymerizable Compound (A2))
The polymerizable compound (A2) (hereinafter, sometimes referred to as "component (A2)" or "compound (A2)") is a polymerizable compound which does not correspond to the component (A1) and has an SP value of 8.88 or less. By using the compound (A2) having an SP value of 8.88 or less, a water contact angle can be developed on the surface after hardening.
The SP value is one of parameter values indicating affinity between raw materials, and is calculated by Fei Duosi (Fedors) as an index of developing hydrophobicity in the present invention.
(A2) The component (C) is a polymerizable compound and has a polymerizable group polymerizable by an active energy ray in its structure. As the polymerizable group, the same compounds as those described in the component (A1) can be used, and the component (A2) is preferably a (meth) acrylate having a (meth) acryloyl group.
The component (A2) in the case of a (meth) acrylate is preferably a compound represented by the following formula (A2-1).
[ solution 6]
In the formula, R 21 Is a hydrogen atom or a methyl group, preferably a hydrogen atom.
Q 21 Is a single bond or a divalent linking group. Examples of the divalent linking group include: substituted alkylene groups, optionally substituted arylene groups, optionally substituted divalent heterocyclic groups, optionally substituted alkenylene groups, or combinations thereof with-O-, -S-, -CO-, - 2 -a divalent linking group in combination. Due to R 22 Is alkyl, therefore Q 21 Preferably alkylene which is not unsubstituted.
Wherein, as Q 21 Preferably a single bond.
R 22 Is an alkyl group having 14 to 22 carbon atoms. The compound represented by the formula (a 2-1) is used in R 22 The hydrophobic compound having a relatively long-chain alkyl group as described above has an SP value of 8.88 or less as the component (A2), and can impart a water contact angle to the composition of the present invention.
R 22 The number of carbon atoms (b) is preferably 16 to 20, more preferably 18 to 20, and particularly preferably 16.
R 22 The alkyl group (b) is preferably a linear alkyl group, and may be a branched alkyl group, because the effect of the present invention can be more remarkably obtained by the linear alkyl group. When the polymer is a branched chain, the number of carbon atoms in the main chain is preferably 14 or more.
(A2) The content of component (a) is preferably 0.1 to 30% by mass, more preferably 0.3 to 20% by mass, even more preferably 0.5 to 10% by mass, and particularly preferably 1 to 5% by mass of component (a).
(other Polymer Compound)
(A) The component (A) may contain other polymer compounds than the components (A1) and (A2). As the other polymer compound, a monofunctional compound having one polymerizable group, a polyfunctional compound having two or more polymerizable groups, and a compound which does not correspond to the components (A1) to (A2) can be suitably used.
As monofunctional compounds, for example, there may be preferably used: monofunctional (meth) acrylates such as n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, phenylbenzyl (meth) acrylate, phenoxyethyl (meth) acrylate, glycidyl (meth) acrylate, morpholine (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, cyclohexylmethyl (meth) acrylate, cyclohexylethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate and dicyclopentenyloxyethyl (meth) acrylate. One or more of these monofunctional (meth) acrylates may be used.
The monofunctional compound is preferably a compound having a viscosity of 300 mPas or less at 25 ℃, more preferably 200 mPas or less. The refractive index is preferably 1.4 or more, more preferably 1.5 or more, and still more preferably 1.55 or more at 25 ℃ and 589 nm.
As the monofunctional compound, phenylbenzyl acrylate represented by the following formula (4) is preferable because the refractive index of the obtained cured product can be easily increased while the viscosity of the composition is appropriately maintained.
[ solution 7]
When the compound represented by formula (4) is used, the content of the compound represented by formula (4) in the active energy ray-polymerizable compound (a) contained in the active energy ray-curable resin composition for optical articles of the present invention is preferably 5 to 30% by mass, more preferably 10 to 20% by mass.
Examples of the polyfunctional compound include: ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, tetrabutylene glycol di (meth) acrylate, 1,4-butylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, polyfunctional (meth) acrylates such as dicyclopentanyl di (meth) acrylate, glycerol di (meth) acrylate, neopentyl glycol hydroxypivalate di (meth) acrylate, caprolactone-modified hydroxypivalate neopentyl glycol di (meth) acrylate, tetrabromobisphenol A di (meth) acrylate, hydroxytrimethylacetaldehyde-modified trimethylolpropane di (meth) acrylate, 1,4-cyclohexanedimethanol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, glycerol tri (meth) acrylate, alkyl-modified dipentaerythritol tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, and the like.
As the polyfunctional (meth) acrylate, for example, a polyfunctional oligomer having an acryloyl group such as urethane (meth) acrylate, polyester (meth) acrylate, epoxy (meth) acrylate, or the like can also be used.
These monofunctional compounds or polyfunctional compounds may be used alone or in combination of two or more.
[ photopolymerization initiator (B) ]
The photopolymerization initiator (B) (hereinafter, may be referred to as "component (B)") is not particularly limited, and various known and conventional initiators can be used. In the production of an article using the composition of the present invention, active energy rays such as ultraviolet rays are often irradiated through the surface of a transparent substrate as a support. Therefore, the component (B) is preferably an initiator having light absorption in a long wavelength region, and is preferably a photopolymerization initiator exhibiting photoinitiation in the ultraviolet ray range of 360 to 450nm, for example.
Examples of the component (B) include: benzophenones such as benzophenone, 3,3 '-dimethyl-4-methoxybenzophenone, 4,4' -bisdimethylaminobenzophenone, 4,4 '-bisdiethylaminobenzophenone, 4,4' -dichlorobenzophenone, michelson, 3,3',4,4' -tetrakis (t-butylperoxycarbonyl) benzophenone, and the like;
xanthones and thioxanthones such as xanthone, thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone and the like; alcohol ketone ethers such as benzoin, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether;
α -diketones such as benzil and diacetyl;
thioethers such as tetramethylthiuram disulfide and p-tolyldisulfide;
benzoic acids such as 4-dimethylaminobenzoic acid and ethyl 4-dimethylaminobenzoate;
3,3' -carbonyl-bis (7-diethylamino) coumarin, 1-hydroxycyclohexyl phenyl ketone, 2,2' -dimethoxy-1,2-diphenylethan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (3536 zxft) phenylphosphine oxide, 1- [4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4-benzoylacetophenone, 4' -dimethylbenzoylacetal, p-dimethylaminoethyl-3926, p-dimethylaminoxyethylthioketone, p-methylacetal 3926, p-dimethylaminoethylthioketone, p-methylacetal 3926, alpha-dichloro-4-phenoxyacetophenone, pentyl-4-dimethylaminobenzoate, 2- (o-chlorophenyl) -4,5-diphenylimidazolyl dimer, 2,4-bis-trichloromethyl-6- [ bis- (ethoxycarbonylmethyl) amino ] phenyl-s-triazine, 2,4-bis-trichloromethyl-6- (4-ethoxy) phenyl-s-triazine, 2,4-bis-trichloromethyl-6- (3-bromo-4-ethoxy) phenyl-s-triazine anthraquinone, 2-t-butylanthraquinone, 2-amylanthraquinone, β -chloroanthraquinone, and the like.
(B) One of the components may be used alone, or two or more of the components may be used in combination.
(B) The amount of the component (a) is not particularly limited, but is preferably 0.05 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and still more preferably 0.5 to 5 parts by mass, per 100 parts by mass of the component (a), from the viewpoint of easy acquisition of appropriate hardenability, and appropriate wear resistance and self-healing properties of the cured product to be obtained.
[ leveling agent (C) ]
The leveling agent (surface conditioner, hereinafter sometimes referred to as "component (C)") is a component for adjusting the state of the surface layer of the coating film formed from the composition of the present invention, and can improve the wear resistance after curing by containing the leveling agent. On the other hand, since the leveling agent reduces the surface tension of the coating film and improves the wettability of the coating film, the use of the leveling agent prevents the water contact angle from being exhibited. In the present invention, by solving the above-mentioned problems by using the component (A2) in combination, the water contact angle can be exhibited even when the component (C) is used, and good abrasion resistance and self-healing properties can be achieved at the same time.
Examples of the component (C) include: acrylic leveling agents, silicon leveling agents, fluorine leveling agents, vinyl leveling agents, and the like. These leveling agents may be used alone or in combination of two or more.
Among these surface control agents, a silicon leveling agent is preferably used from the viewpoint of improving self-healing properties. Examples of the silicon leveling agent include BYK series produced by BYK-Chemie Japan, inc. of Bi Kehua, japan.
The content of (C) is preferably 0.005 to 10 parts by mass, more preferably 0.01 to 5 parts by mass, and still more preferably 0.1 to 1 part by mass, relative to 100 parts by mass of the component (a).
The active energy ray-curable resin composition of the present invention may optionally contain other components than the components (a) to (C) as additives. The additive is not particularly limited as long as it does not correspond to the components (A) to (C), and includes: a photo sensitizer, an ultraviolet absorber, an antioxidant, a silicon-based additive, a fluorine-based additive, a rheology control agent, a defoaming agent, a mold release agent, a silane coupling agent, an antistatic agent, an antifogging agent, a colorant, an inorganic filler, and the like.
The active energy ray-curable resin composition for optical articles of the present invention may optionally contain a solvent, and when the content of the solvent is small, an active energy ray-curable resin composition for optical articles which is less likely to cause contamination to the working environment can be obtained, and therefore, it is preferable. Specifically, the content of the solvent in the active energy ray-curable resin composition for optical articles of the present invention is preferably 1% by mass or less, and preferably substantially none.
Examples of the photosensitizers include: amines, ureas, sulfur-containing compounds, phosphorus-containing compounds, chlorine-containing compounds, nitriles, or other nitrogen-containing compounds.
Examples of the ultraviolet absorber include: 2- [4- { (2-hydroxy-3-dodecyloxypropyl) oxy } -2-hydroxyphenyl ] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, triazine derivatives such as 2- [4- { (2-hydroxy-3-tridecyloxypropyl) oxy } -2-hydroxyphenyl ] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2 '-xanthenecarboxy-5' -methylphenyl) benzotriazole, 2- (2 '-o-nitrobenzyloxy-5' -methylphenyl) benzotriazole, 2-xanthenecarboxy-4-dodecyloxybenzone, 2-o-nitrobenzyloxy-4-dodecyloxybenzone, and the like.
Examples of the antioxidant include: hindered phenol antioxidants, hindered amine antioxidants, organic sulfur antioxidants, phosphate antioxidants, and the like.
Examples of the silicon-based additive include: polyorganosiloxanes having an alkyl group or a phenyl group such as dimethylpolysiloxane, methylphenylpolysiloxane, cyclic dimethylpolysiloxane, methylhydrogenpolysiloxane, polyether-modified dimethylpolysiloxane copolymer, polyester-modified dimethylpolysiloxane copolymer, fluorine-modified dimethylpolysiloxane copolymer, amino-modified dimethylpolysiloxane copolymer, etc.
The inorganic filler (inorganic nanoparticles) is preferably a filler having a high refractive index, and includes alumina, zirconia, titania, a compound of these, a mixed oxide of these, or a metal oxide of these. These inorganic nanoparticles have a higher refractive index than general organic materials and are therefore effective as means for increasing the refractive index of a cured product, but it is necessary to consider the balance between the strength of the molded product and the adhesion to the substrate, and it is practical to use, as the blending amount, 20 to 60 mass% of inorganic nanoparticles with respect to the total amount of component (a) and inorganic nanoparticles. Among them, in order to achieve both high refractive index and self-healing property, it is more preferably 30 to 50 mass%.
The amount of each of the additives is not particularly limited as long as the effect is sufficiently exhibited and the curing by the active energy ray is not inhibited, and is preferably 0.05 to 20 parts by mass, and more preferably 0.1 to 10 parts by mass, respectively, with respect to 100 parts by mass of the composition.
The composition of the present invention may optionally contain a solvent, and the content of the solvent is preferably small from the viewpoint of environmental pollution. Specifically, the solvent content in the composition is preferably 1% by mass or less.
The active energy ray-curable resin composition of the present invention has a viscosity of preferably 50 to 5000 mPas, more preferably 100 to 2000 mPas at 25 ℃ in terms of easy application and molding into a desired shape or thickness in various optical article applications. Particularly, when applied to a prism sheet, the master mold is preferably 50 to 800mPa · s, from the viewpoint of ease of uniform application to the prism sheet and ease of replication of the master mold having a fine uneven structure (speed of the production line can be increased).
Even if the viscosity is outside the above range, the viscosity can be adjusted by controlling the temperature of the composition.
The acid value (the number of milligrams of potassium hydroxide required to neutralize the acid component present in 1g of the sample by a predetermined method) of the active energy ray-curable resin composition of the present invention is preferably 5.0mgKOH/g or less, and particularly preferably 0mgKOH/g to 3.0mgKOH/g.
< hardening substance >
The active energy ray-curable resin composition of the present invention can be applied to a substrate or formed into a cured product by irradiation with an active energy ray according to the intended use. Examples of the active energy ray include electron beam, ultraviolet ray, and visible ray. When an electron beam is used as the active energy ray, the curable resin composition of the present invention can be cured using an electron beam generator such as a kockcrofton (Cockcroft-Walton) type accelerator, a Van der Graaff (Van de Graaff) type electron accelerator, a resonant transformer type accelerator, an insulated core transformer type, a high frequency high voltage accelerator (dynamitron) type, a linear filament (linear filament) type, or a high frequency type. When ultraviolet light is used as the active energy ray, the ultraviolet light can be irradiated and cured by a mercury lamp such as an ultra-high pressure mercury lamp, a high pressure mercury lamp, or a low pressure mercury lamp, a xenon lamp, a carbon arc, a metal halide lamp, or a high power light emitting diode-ultraviolet (LED-UV) lamp.
The refractive index of the cured product of the active energy ray-curable resin composition of the present invention is preferably 1.50 or more, more preferably 1.54 or more, still more preferably 1.55 or more, and particularly preferably 1.56 or more. The cured product has a high refractive index and appropriate scratch resistance, and thus can be suitably used for various optical articles.
The hardness of the cured product of the present invention may be appropriately designed according to various uses, and for example, when used for a prism sheet, the elastic modulus at 25 ℃ is preferably 5MPa to 500MPa, and more preferably 10MPa to 100MPa. When the elastic modulus is in the above range, the balance between the mechanical strength and the toughness (elongation) is good, and the restoring force necessary for the self-healing property is easily exhibited.
The elastic modulus is a value obtained by performing dynamic viscoelasticity measurement under conditions of a temperature rise rate of 3 ℃/Min and a frequency of 3.5Hz as measurement conditions using "RSAII" manufactured by Rheometric Scientific as a viscoelasticity measuring apparatus.
The glass transition temperature Tg of the cured product of the present invention is preferably 40 ℃ or lower, more preferably 30 ℃ or lower, and particularly preferably 25 ℃ or lower. By setting the glass transition temperature, it is easy to achieve both a high refractive index and good self-healing properties. The lower limit of Tg is not particularly limited, but is preferably 5 ℃ or higher, more preferably 10 ℃ or higher, and particularly preferably 15 ℃ or higher.
In the present invention, the Tg can be easily adjusted by using the components (a) to (C) or blending them within a preferable range.
The glass transition temperature is a value read with the temperature of the peak position of tan δ represented by the ratio of the storage elastic modulus E' to the complex elastic modulus E ″ obtained in the viscoelasticity measurement as Tg.
[ optical sheet ]
The optical sheet of the present invention is an optical sheet having a layer containing a cured product of the active energy ray-curable resin composition. The optical sheet is an optical sheet in which a prism or a lens including the cured product is laminated on a transparent resin film, and specifically, the following examples are given: a prism sheet used for a display such as a liquid crystal display device, a lenticular sheet used for a stereograph, a projection screen, or the like, a fresnel lens sheet used for a condenser lens of an overhead projector, or an optical sheet such as a diffraction grating used for a color filter.
Examples of the method for producing these optical sheets include the following methods: after filling the active energy ray-curable resin composition into a master mold having a fine shape required for various applications, a base material is pressure-laminated on the filled resin composition without mixing air, and the resin composition is cured by irradiating active energy rays such as ultraviolet rays from the base material side, and then released from the master mold. Further, for example, the following continuous production method can be mentioned: after the roll-shaped master mold is continuously filled with the resin composition, a base material is continuously brought into close contact with the filled resin composition without mixing air, and the resin composition is cured by irradiating the base material side with an active energy ray such as ultraviolet light, and then the roll-shaped master mold is released from the mold.
As the substrate for forming the optical sheet, a film-like, sheet-like, or plate-like transparent substrate can be used. The material of the substrate may be selected as appropriate depending on the application, and examples thereof include: polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylic resins such as triacetyl cellulose, polycarbonate resins and methyl methacrylate copolymers, styrene resins, polysulfone resins, polyether sulfone resins, vinyl chloride resins, polymethacrylimide resins, and the like. In addition, an inorganic substrate such as a glass substrate can be used in the same manner.
The active energy ray-curable resin composition of the present invention can be suitably applied to prism sheets for various displays among various optical sheets. The prism sheet has a plurality of fine prism-shaped portions on one surface of a sheet-like molded body, and is generally arranged on the back surface (light source side) of a liquid crystal display element so that the prism surface faces the element side.
The prism sheet is a sheet having a prism layer comprising a cured product of the active energy ray-curable resin composition on a transparent film, and the shape of the prism layer is preferably an angle θ of a prism apex angle of 70 ° to 110 °, more preferably 75 ° to 110 °, and particularly preferably 80 ° to 95 °, in terms of excellent light-condensing properties and improved brightness.
The pitch of the prisms is preferably 100 μm or less, and particularly preferably 70 μm or less in terms of preventing the generation of moire patterns on the screen and further improving the fineness of the screen. The height of the irregularities of the prism is determined by the angle θ of the apex angle of the prism and the pitch of the prism, and is preferably 50 μm or less. Further, the thickness of the prism lens sheet is preferably large in terms of strength, but is preferably small in order to optically suppress light absorption, and these balance are preferably 50 μm to 1000 μm.
[ examples ]
The present invention will be described in more detail below with reference to examples and comparative examples. In the examples, all parts and% are by mass unless otherwise specified. The characteristics and the like in examples and comparative examples were measured and evaluated as follows.
< refractive index >
The refractive indices of the resin compositions prepared in examples and comparative examples were measured using a multi-wavelength abbe refractometer (DR-M2) manufactured by atoo (ATAGO) and a reference wavelength (589 nm). The values in the table represent the refractive index of the formulated composition.
< viscosity >
The viscosities of the resin compositions prepared in examples and comparative examples were measured at 25 ℃ using a model-E viscometer (TV-25, model (type) H) manufactured by eastern industries.
< self-healing >
The resin compositions prepared in examples and comparative examples were filled in a prism master model having a prism pitch interval of 50 μm, a prism height of 25 μm and a vertex angle of 90 °, a 125 μm PET film was laminated on the resin master model, pressure was applied to the PET film by a roller, and then the laminated PET film was laminated from the PET film side by a high-pressure mercury lamp so that the cumulative light amount was 400mJ/cm 2 The resin composition is cured by the irradiation amount of (2) to form a prism sheet. By using an awl to moveThe obtained prism sheet was scratched by about 3cm, and the time until the scratch (line) appeared until the scratch disappeared was visually observed, and evaluated according to the following criteria.
5: instant recovery (scar disappearance)
4: recovery within 10 seconds (scar disappearing)
3: recovery within 1 minute (scar disappearance)
2: recovery within 5 minutes (scar disappearance)
1: recovery for more than 15 minutes (scar disappeared)
0: is not recovered
< abrasion resistance >
A diffusion film cut into a circular shape having a diameter of 1cm was placed on the prism sheet obtained in the same manner as described above, and a load of 400g was applied, and the prism sheet was subjected to reciprocal rubbing 40 times at a distance of 10cm using an abrasion resistance tester (IMC-15 FA type) manufactured by gmbh of wellyuan manufacturing, and a belt-like scratch on the surface was evaluated based on the area of the scratch. The evaluation was carried out indoors at 23 ℃, and the evaluation was carried out according to the following criteria, and a or more was regarded as a pass.
A: the area of the scar part was 5cm 2 The following
B: the area of the scar part is more than 5cm 2 And is 7cm 2 The following are provided
C: the area of the scar part is more than 7cm 2
< Water contact Angle >
50 μ l of ion exchange water was pushed out from a syringe onto the prism sheet obtained in the same manner as described above, and the water contact angle was measured using a water contact angle meter (model DMo-501) manufactured by synergetics interface science. The evaluation was carried out in a room at 23 ℃, and the results of the measurement were evaluated as follows, when observed from a direction horizontal to the ridge line of the prism sheet. B or more is defined as passed.
A: a water contact angle of 50 DEG or more after dropping for 1 second and a water contact angle retention rate of 80% or more after 5 minutes
B: the water contact angle after dropping for 1 second is 50 DEG or more and the water contact angle retention rate after 5 minutes is less than 80%
C: a water contact angle of 30 DEG or more and less than 50 DEG after dropping for 1 second, and a water contact angle retention rate of 80% or more after 5 minutes
D: the contact angle of water after dropping for 1 second is 30-50 DEG, and the retention rate of the contact angle of water after 5 minutes is 80%
E: the water contact angle after dropping for 1 second is less than 30 °
(examples 1 to 4 and comparative examples 1 to 5)
The compounds were melt mixed according to the formulation shown in the following table, and the resin composition was adjusted. The alkylene oxide content (mmol/g) of the polymerizable compound (A1) is shown in the table as "alkylene oxide content".
The evaluation was performed using the obtained resin composition. In addition, the amount of the composition in the table is% by mass.
[ Table 1]
[ Table 2]
The compounds shown in the above tables are as follows.
A1-1: ethylene oxide-modified bisphenol A diacrylate ("Miramer M-2200" manufactured by Meiyuan (MIWON) Co., ltd., R in the formula (a 1-1) 1 And R 2 Is a hydrogen atom, X 1 And X 2 Is a compound of ethylene, m + n =20, the ethylene oxide modification amount is 20 mol)
A1-2: ethylene oxide-modified bisphenol A diacrylate ("Miramer M-2100" manufactured by MIWON corporation), R in the formula (a 1-1) 1 And R 2 Is a hydrogen atom, X 1 And X 2 Is a compound of ethylene, m + n =10, the ethylene oxide modification amount is 10 mol)
A1-3: ethylene oxide-modified acrylate of o-phenylphenol ("Miramer) M-1142" manufactured by Meiyuan (MIWON) Co., ltd., R in the formula (a 1-2) 11 Is a hydrogen atom, X 12 Ethylene, a compound with p =1, an ethylene oxide modification amount of 1 mol)
A2-1: stearyl acrylate (SP value: 8.80) (Bank Mei Laite (KOMERATE) A189 "manufactured by KPX, inc. in the formula (a 2-1) R 21 Is a hydrogen atom, Q 21 Is a single bond, R 22 A compound having a linear carbon number of 18)
A2-2: cetyl acrylate (SP value: 8.83) (Bank Mei Laite (KOMERATE) A169, manufactured by KPX, inc.; R in said formula (a 2-1) 21 Is a hydrogen atom, Q 21 Is a single bond, R 22 A compound having a linear carbon number of 16)
A2-3: dodecyl acrylate (SP value: 8.89) (Bank Mei Laite (KOMERATE) A129 "manufactured by KPX, inc.; R in the formula (a 2-1) 21 Is a hydrogen atom, Q 21 Is a single bond, R 22 A compound having a linear chain of carbon number 12)
A2-4: behenyl acrylate (SP value: 8.77) (Bank Mei Laite (KOMERATE) A229 "manufactured by KPX, inc., R in the formula (A2-1) 21 Is a hydrogen atom, Q 21 Is a single bond, R 22 A compound having a linear carbon number of 22)
A2-5: stearyl methacrylate (SP value: 8.74) (Bank Mei Laite (KOMERATE) A189M manufactured by KPX, inc.; R in said formula (a 2-1) 21 Is methyl, Q 21 Is a single bond, R 22 A compound having a linear carbon number of 18)
A2-6: isobornyl acrylate (SP value: 9.93) ("IBXA" manufactured by Osaka organic chemical industries, ltd., R in said formula (a 2-1) 21 Is a hydrogen atom corresponding to R 22 Or Q 21 Compounds in which the moiety (a) is isobornyl
A2-7: dicidol diacrylate (SP value: 11.30) (Kcl. Mei Laite (KOMERATE) D0013 "manufactured by KPX Co., ltd., R in the formula (a 2-1) 21 Is a hydrogen atom corresponding to R 22 Or Q 21 The moiety of (2) has a tricyclodecane skeleton including a monoacrylate)
A2-8: cyclohexyl acrylate (SP value: 10.04) ("Biscott (VISCOTE) #155" manufactured by Osaka organic chemical industries, ltd., R in said formula (a 2-1)) 21 Is a hydrogen atom corresponding to R 22 Or Q 21 Compound (b) with a moiety of cyclohexyl
B1: 1-Hydroxycyclohexylphenylketone ("OMNIRAD) 184", manufactured by IGM resin B.V. (IGM RESINS B.V.)
C1: polyether-modified polydimethylsiloxane ("BYK-333" manufactured by BYK-Chemie Japan, inc. of Bi Kehua Japan)
As is clear from the above results, the active energy ray-curable resin composition of the present invention was confirmed to have an excellent balance between the development of water contact angle and self-healing properties or abrasion resistance.
On the other hand, it was confirmed that comparative example 2 to comparative example 5, in which comparative example 1 having an alkylene oxide content of less than 0.6mmol/g was poor in self-healing properties and abrasion resistance and did not contain a polymerizable compound having an SP value of 8.88 or less, did not exhibit a water contact angle and could not suppress adhesion of water.
[ industrial applicability ]
The active energy ray-curable resin composition of the present invention can be suitably used for various optical members represented by prism sheets and the like, as described above.
Claims (8)
1. An active energy ray-curable resin composition comprising a polymerizable compound (A), a photopolymerization initiator (B) and a leveling agent (C), characterized in that,
the polymerizable compound (A) contains a polymerizable compound (A1) having an alkylene oxide chain in the structure and a polymerizable compound (A2) having an SP value of 8.88 or less, and
the polymerizable compound (A1) is contained so that the content of the alkylene oxide chain in the structure of the compound is 0.6mmol/g or more based on the total amount of the composition.
2. The active energy ray-curable resin composition according to claim 1, wherein a compound represented by the following formula (A2-1) is contained as the polymerizable compound (A2),
in the formula, R 21 Is a hydrogen atom or a methyl group, Q 21 Is a single bond or a divalent linking group, R 22 Is an alkyl group having 14 to 22 carbon atoms.
3. The active energy ray-curable resin composition according to claim 1 or 2, wherein a compound represented by the following formula (A1-1) is contained as the polymerizable compound (A1),
in the formula, R 1 And R 2 Each independently represents a hydrogen atom or a methyl group, X 1 And X 2 Independently represents an alkylene group having 2 or 3 carbon atoms, m and n independently represent an integer of 1 or more, and m + n is 20 or more.
4. The active energy ray-curable resin composition according to claim 1 or 2, wherein a compound represented by the following formula (A1-2) is contained as the polymerizable compound (A1),
in the formula, R 11 Represents a hydrogen atom or a methyl group, X 12 Represents an alkylene group having 2 or 3 carbon atoms, and p represents an integer of 1 or more.
5. The active energy ray-curable resin composition according to claim 1 or 2, wherein the proportion of the polymerizable compound (A2) in the active energy ray-polymerizable compound (a) is 0.1 to 30% by mass.
6. The active energy ray-curable resin composition according to claim 1 or 2, wherein the proportion of the polymerizable compound (A1) in the active energy ray-polymerizable compound (a) is 30 to 95% by mass.
7. A cured product of the active energy ray-curable resin composition according to any one of claims 1 to 6, having a refractive index of 1.54 or more.
8. An optical sheet having a layer containing the cured product according to claim 7.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021116981A JP2023013069A (en) | 2021-07-15 | 2021-07-15 | Active energy ray-curable resin composition, cured product and optical sheet |
| JP2021-116981 | 2021-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115612382A true CN115612382A (en) | 2023-01-17 |
Family
ID=84857574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210794541.0A Pending CN115612382A (en) | 2021-07-15 | 2022-07-07 | Active energy ray-curable resin composition, cured product, and optical sheet |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2023013069A (en) |
| CN (1) | CN115612382A (en) |
| TW (1) | TW202305019A (en) |
-
2021
- 2021-07-15 JP JP2021116981A patent/JP2023013069A/en active Pending
-
2022
- 2022-07-07 CN CN202210794541.0A patent/CN115612382A/en active Pending
- 2022-07-12 TW TW111126160A patent/TW202305019A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2023013069A (en) | 2023-01-26 |
| TW202305019A (en) | 2023-02-01 |
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