JP5441311B2 - 重合性組成物 - Google Patents
重合性組成物 Download PDFInfo
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- JP5441311B2 JP5441311B2 JP2007030050A JP2007030050A JP5441311B2 JP 5441311 B2 JP5441311 B2 JP 5441311B2 JP 2007030050 A JP2007030050 A JP 2007030050A JP 2007030050 A JP2007030050 A JP 2007030050A JP 5441311 B2 JP5441311 B2 JP 5441311B2
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- ring
- oco
- independently
- meth
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- 239000000203 mixture Substances 0.000 title claims description 87
- -1 acrylate compound Chemical class 0.000 claims description 105
- 239000010408 film Substances 0.000 claims description 44
- 239000004973 liquid crystal related substance Substances 0.000 claims description 37
- 229920006254 polymer film Polymers 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 230000001588 bifunctional effect Effects 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000007870 radical polymerization initiator Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- 101150065749 Churc1 gene Proteins 0.000 claims description 6
- 102100038239 Protein Churchill Human genes 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 claims description 2
- 239000012788 optical film Substances 0.000 claims description 2
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- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 32
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- 238000000034 method Methods 0.000 description 23
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
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- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
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- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 229910000271 hectorite Inorganic materials 0.000 description 2
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000003381 stabilizer Substances 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- OURODNXVJUWPMZ-UHFFFAOYSA-N 1,2-diphenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 OURODNXVJUWPMZ-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 description 1
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- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- IJXPXNZUSXLSTF-UHFFFAOYSA-N 2-[2-(4-butoxyphenyl)ethenyl]-5-(trichloromethyl)-1,3,4-oxadiazole Chemical compound C1=CC(OCCCC)=CC=C1C=CC1=NN=C(C(Cl)(Cl)Cl)O1 IJXPXNZUSXLSTF-UHFFFAOYSA-N 0.000 description 1
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- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- NZTUTWYBJCOZCO-UHFFFAOYSA-N 4-methoxy-2-phenyl-4,6-bis(trichloromethyl)-1h-1,3,5-triazine Chemical compound N1C(C(Cl)(Cl)Cl)=NC(OC)(C(Cl)(Cl)Cl)N=C1C1=CC=CC=C1 NZTUTWYBJCOZCO-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- FMWQYKDNAFZCNB-UHFFFAOYSA-N 9,10-dimethylbenzo[a]phenazine Chemical compound C1=CC=CC2=C(N=C3C(C=C(C(=C3)C)C)=N3)C3=CC=C21 FMWQYKDNAFZCNB-UHFFFAOYSA-N 0.000 description 1
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F220/42—Nitriles
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- C—CHEMISTRY; METALLURGY
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- C09K19/00—Liquid crystal materials
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- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K19/38—Polymers
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- C—CHEMISTRY; METALLURGY
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- 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
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3083—Birefringent or phase retarding elements
Description
本発明の重合性組成物は、上記一般式(1)で表される二官能(メタ)アクリレート化合物及び上記一般式(2)で表される単官能(メタ)アクリレート化合物以外に、以下に述べる任意成分を含んでもよく、その場合、本発明の重合性組成物(但し、溶剤を除く)中、上記一般式(1)で表される二官能(メタ)アクリレート化合物及び上記一般式(2)で表される単官能(メタ)アクリレート化合物の含有量の合計の和は、少なくとも50質量%以上であることが好ましく、70質量%以上であることが特に好ましい。
また、本発明の重合性組成物は、少なくとも室温付近、具体的には30℃以下で液晶相を示すことが好ましく、特に15℃以下で液晶相を示すことがより好ましい。
ただし、本発明の重合性組成物を用いて作製される重合膜の耐熱性及び光学特性を付与するために、他の単量体の含有量は、上記二官能(メタ)アクリレート化合物及び上記単官能(メタ)アクリレート化合物の合計100質量部に対して、50質量部以下が好ましく、特に30質量部以下がより好ましい。
界面活性剤の好ましい使用割合は、界面活性剤の種類、組成物の成分比などに依存するが、本発明の重合性組成物中、100ppmから5質量%の範囲であることが好ましく、特に0.05から1質量%の範囲が好ましい。
下記の手順([1]重合性組成物溶液の調製、[2]支持基板の製作、[3]支持基板への塗布)に従い本発明の重合性組成物から重合膜を作製した。
下記〔表1〕に記載の重合性組成物1.0gを溶媒(シクロヘキサノン/2−ブタノン=1/1(質量%))4gに添加して溶解した後、ラジカル重合開始剤(N−1919;株式会社ADEKA製)0.03gを加えて完全に溶解した後に、0.45μmフィルターでろ過処理を実施して重合性組成物溶液を調製した。
中性洗剤で洗浄後、純水で洗い流し乾燥したガラス板にポリビニルアルコール5%水溶液を、スピンコーターで均一に塗工し、100℃で3分間乾燥させた。乾燥後、ガラス基板に指示されたポリビニルアルコールの表面をレーヨン布で一定方向に擦り、塗布用支持基板を製作した。
上記[1]で調製した溶液を上記[2]で製作した支持基板上にスピンコーターで膜厚が約1.0μmになるように回転数及び時間を調整して塗工し、ホットプレートを用いて100℃で3分間乾燥後、室温下で5分間冷却し、高圧水銀灯(120W/cm)を20秒間照射して硬化して重合膜を得た。
上記方法で得られた重合膜について、以下の方法で評価を行った。
上記の方法で得られた重合膜に対して、偏光顕微鏡を用いてセナルモン法に基づく複屈折測定法に従い、室温25℃で波長546nmにおけるリターデーション(R)を測定した。
得られた重合膜に対して、触針式表面形状測定器(Dektak6M;(株)アルバック製)を用いて室温25℃で膜厚(d)を測定した。
重合膜の光学(屈折率)異方性(Δn)は、下記の関係式において上記のリターデーション(R)及び膜厚(d)を代入して、重合膜の光学(屈折率)異方性(Δn)を算出した。
光学(屈折率)異方性(Δn)=リターデーション(R)/膜厚(d)
重合膜の均質性について偏光顕微鏡を用いて評価した。試料を、クロスニコル下で重合膜を設置したステージを回転させることによって、重合膜の配向状態を観察し、膜の均質性について評価した。重合膜の配向が均一に得られていれば○、配向が得られても不均一であれば△、重合膜に結晶等が発生して配向が全く得られていなければ×とした。
上記[1]で調製した重合性組成物溶液をスピンコーターで塗工し、ホットプレートを用いて100℃で3分間乾燥後直ちに25℃の室温下に放置し、液晶状態の安定性を評価した。安定性の評価は、室温下に放置後2時間以上液晶状態を保った場合は◎、1時間を超えて2時間までに結晶が析出した場合は○、30分を超えて1時間までの場合は△、30分以内に結晶が析出した場合は×とした。
下記〔表2〕に記載の重合性組成物を〔実施例1〕と同様にして重合膜を作製し、製膜安定性の評価を実施し、本発明の重合性組成物に用いられる二官能(メタ)アクリレート化合物と単官能(メタ)アクリレート化合物との好適配合組成を評価した。これらの結果について〔表2〕に示す。尚、実施例1−3及び比較例1−5の重合膜についての製膜安定性の評価も〔表2〕に併せて記載した。
コレステリック液晶相の発現する系である下記〔表3〕に記載の重合性組成物1.0gを溶媒(2−ブタノン)4gに添加して溶解した後、ラジカル重合開始剤(N−1919;株式会社ADEKA製)0.03gを加え、完全に溶解させた後に0.45μmフィルターでろ過処理を実施して重合性組成物の溶液を調製し、上記〔実施例1〕で製作した支持基板上にスピンコーターで調整した溶液を均一に塗工し、ホットプレートを用いて100℃で3分間乾燥後、室温下で1分間冷却し、高圧水銀灯(120W/cm)で20秒間照射して硬化させることによって重合膜を得た。得られた重合膜について選択反射と膜の均質性の評価を実施した。これらの結果について〔表3〕に併せて示す。
Claims (9)
- 下記一般式(1)で表される二官能(メタ)アクリレート化合物と、下記一般式(2)で表される末端にニトリル基を有する単官能(メタ)アクリレート化合物とからなり、それらの質量比率(前者/後者)が90/10〜40/60である重合性組成物。
- 上記一般式(3)で表される二官能(メタ)アクリレート化合物において、環A1及び環A3がベンゼン環又はナフタレン環である請求項2又は3記載の重合性組成物。
- 30℃以下で液晶相を示す請求項1〜4の何れか1項に記載の重合性組成物。
- さらに、光学活性化合物を含有し、コレステリック液晶相を発現する請求項1〜5の何れか1項に記載の重合性組成物。
- さらに、ラジカル重合開始剤及び界面活性剤を含有する請求項1〜6の何れか1項に記載の重合性組成物。
- 請求項1〜7の何れか1項に記載の重合性組成物が液晶相を示す状態で、光重合させることにより作製された重合膜。
- 請求項8記載の重合膜を使用してなるディスプレイ用光学フィルム。
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JP2007030050A JP5441311B2 (ja) | 2007-02-09 | 2007-02-09 | 重合性組成物 |
US12/519,474 US7931825B2 (en) | 2007-02-09 | 2008-01-07 | Polymerizable composition |
EP08702914.6A EP2110390B1 (en) | 2007-02-09 | 2008-01-07 | Polymerizable composition |
KR1020097013557A KR101441092B1 (ko) | 2007-02-09 | 2008-01-07 | 중합성 조성물 |
CN2008800015885A CN101583638B (zh) | 2007-02-09 | 2008-01-07 | 聚合性组合物 |
PCT/JP2008/050033 WO2008096556A1 (ja) | 2007-02-09 | 2008-01-07 | 重合性組成物 |
TW097101838A TWI448478B (zh) | 2007-02-09 | 2008-01-17 | Polymerizable composition |
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TWI448478B (zh) | 2014-08-11 |
US7931825B2 (en) | 2011-04-26 |
TW200906865A (en) | 2009-02-16 |
KR20090116695A (ko) | 2009-11-11 |
CN101583638A (zh) | 2009-11-18 |
KR101441092B1 (ko) | 2014-09-19 |
JP2008195762A (ja) | 2008-08-28 |
EP2110390A4 (en) | 2013-03-06 |
EP2110390B1 (en) | 2014-07-02 |
WO2008096556A1 (ja) | 2008-08-14 |
EP2110390A1 (en) | 2009-10-21 |
CN101583638B (zh) | 2012-11-14 |
US20100090163A1 (en) | 2010-04-15 |
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