JPWO2015025836A1 - 含フッ素ウレタン(メタ)アクリレート、硬化性組成物及び反射防止フィルム - Google Patents
含フッ素ウレタン(メタ)アクリレート、硬化性組成物及び反射防止フィルム Download PDFInfo
- Publication number
- JPWO2015025836A1 JPWO2015025836A1 JP2015532859A JP2015532859A JPWO2015025836A1 JP WO2015025836 A1 JPWO2015025836 A1 JP WO2015025836A1 JP 2015532859 A JP2015532859 A JP 2015532859A JP 2015532859 A JP2015532859 A JP 2015532859A JP WO2015025836 A1 JPWO2015025836 A1 JP WO2015025836A1
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- Prior art keywords
- acrylate
- meth
- fluorine
- refractive index
- containing urethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 156
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 85
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 239000011737 fluorine Substances 0.000 title claims abstract description 73
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000005647 linker group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 238000000576 coating method Methods 0.000 claims description 34
- 239000011248 coating agent Substances 0.000 claims description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 239000010419 fine particle Substances 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000010408 film Substances 0.000 description 59
- 239000010410 layer Substances 0.000 description 46
- -1 fluoroethylene, trifluoroethylene, chlorotrifluoroethylene, 1,2-dichloro-1,2-difluoroethylene Chemical group 0.000 description 35
- 229920005989 resin Polymers 0.000 description 28
- 239000011347 resin Substances 0.000 description 28
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 27
- 239000008199 coating composition Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 20
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- 239000002904 solvent Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 13
- 238000005259 measurement Methods 0.000 description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 11
- 239000002994 raw material Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000008034 disappearance Effects 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- QASBHTCRFDZQAM-UHFFFAOYSA-N (2-isocyanato-2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)N=C=O QASBHTCRFDZQAM-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000006117 anti-reflective coating Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000002310 reflectometry Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Chemical group 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 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 1
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- 229910001507 metal halide Inorganic materials 0.000 description 1
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 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
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- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
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- 238000006068 polycondensation reaction Methods 0.000 description 1
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- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000010557 suspension polymerization 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
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 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
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 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
- 238000004383 yellowing Methods 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
(1)まず基材にハードコート材を塗布・硬化してハードコート層を形成する。
(2)上記のハードコート層に本発明の反射防止塗料組成物を塗布・硬化して低屈折率層の塗膜を形成する。この低屈折率層が反射防止フィルムの最表面となる。
なお、上記ハードコート層と低屈折率層との間に、中屈折率層及び/又は高屈折率層を設けても構わない。
装置:日本分光株式会社製「FT/IR−6100」
測定方法:KBr法
装置:日本電子株式会社製「JNM−ECA500」
溶媒:重水素化クロロホルム
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテックジャパン株式会社製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、1,3−ビス(3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロオクチルオキシ)−2−プロパノール151.5g、p−メトキシフェノール0.02g、2−エチルヘキサン酸スズ0.3gを仕込み、乾燥空気気流下にて攪拌しながら60℃に昇温した。次いで、1,1−ビス(アクリロイルオキシメチル)エチルイソシアネート48.5gを滴下装置にセットし、フラスコ内を60℃に保ちながら1時間かけて滴下した。滴下終了後、60℃で15分間攪拌した後、90℃に昇温して9時間攪拌することにより反応を行った結果、IRスペクトル測定によりイソシアネート基の消失が確認されたので、フィルターで濾過して本発明の含フッ素ウレタンアクリレート(I−1)200gを得た。含フッ素ウレタンアクリレート(I−1)をGPCで測定した結果、数平均分子量1,010、重量平均分子量1,012であった。25℃の屈折率を測定した結果、1.383であった。また、フッ素含有率は、原料組成から計算した結果、47.7質量%であった。なお、含フッ素ウレタンアクリレート(I−1)のIRスペクトルのチャート図を図1に、13C−NMRスペクトルのチャート図を図2に、1H−NMRスペクトルのチャート図を図3に、19F−NMRスペクトルのチャート図を図4に、GPCのチャート図を図5に示す。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、1,3−ビス(3,3,4,4,5,5,6,6,6−ノナフルオロヘキシルオキシ)−2−プロパノール139.9g、p−メトキシフェノール0.02g、2−エチルヘキサン酸スズ0.3gを仕込み、乾燥空気気流下にて攪拌しながら60℃に昇温した。次いで、1,1−ビス(アクリロイルオキシメチル)エチルイソシアネート60.1gを滴下装置にセットし、フラスコ内を60℃に保ちながら1時間かけて滴下した。滴下終了後、60℃で15分間攪拌した後、90℃に昇温して9時間攪拌することにより反応を行った結果、IRスペクトル測定によりイソシアネート基の消失が確認されたので、フィルターで濾過して本発明の含フッ素ウレタンアクリレート(I−2)200gを得た。含フッ素ウレタンアクリレート(I−2)をGPCで測定した結果、数平均分子量714、重量平均分子量716であった。25℃の屈折率を測定した結果、1.399であった。また、フッ素含有率は、原料組成から計算した結果、41.0質量%であった。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、1,3−ビス(3,3,4,4,4−ペンタフルオロブチルオキシ)−2−プロパノール121.9g、p−メトキシフェノール0.02g、2−エチルヘキサン酸スズ0.3gを仕込み、乾燥空気気流下にて攪拌しながら60℃に昇温した。次いで、1,1−ビス(アクリロイルオキシメチル)エチルイソシアネート78.1gを滴下装置にセットし、フラスコ内を60℃に保ちながら1時間かけて滴下した。滴下終了後、60℃で15分間攪拌した後、90℃に昇温して9時間攪拌することにより反応を行った結果、IRスペクトル測定によりイソシアネート基の消失が確認されたので、フィルターで濾過して本発明の含フッ素ウレタンアクリレート(I−3)200gを得た。含フッ素ウレタンアクリレート(I−3)をGPCで測定した結果、数平均分子量615、重量平均分子量617であった。25℃の屈折率を測定した結果、1.425であった。また、フッ素含有率は、原料組成から計算した結果、30.2質量%であった。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、1,3−ビス(3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロオクチルオキシ)−2−プロパノール168.2g、p−メトキシフェノール0.02g、2−エチルヘキサン酸スズ0.3gを仕込み、乾燥空気気流下にて攪拌しながら60℃に昇温した。次いで、アクリロイルオキエチルイソシアネート31.8gを滴下装置にセットし、フラスコ内を60℃に保ちながら1時間かけて滴下した。滴下終了後、60℃で15分間攪拌した後、90℃に昇温して9時間攪拌することにより反応を行った結果、IRスペクトル測定によりイソシアネート基の消失が確認されたので、フィルターで濾過して比較対照用含フッ素ウレタンアクリレート(I´−1)200gを得た。比較対照用含フッ素ウレタンアクリレート(I´−1)をGPCで測定した結果、数平均分子量913、重量平均分子量915であった。25℃の屈折率を測定した結果、1.369であった。また、フッ素含有率は、原料組成から計算した結果、53.0質量%であった。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、1,3−ビス(3,3,3−トリフルオロプロピルオキシ)−2−プロパノール106.2g、p−メトキシフェノール0.02g、2−エチルヘキサン酸スズ0.3gを仕込み、乾燥空気気流下にて攪拌しながら60℃に昇温した。次いで、1,1−ビス(アクリロイルオキシメチル)エチルイソシアネート93.8gを滴下装置にセットし、フラスコ内を60℃に保ちながら1時間かけて滴下した。滴下終了後、60℃で15分間攪拌した後、90℃に昇温して9時間攪拌することにより反応を行った結果、IRスペクトル測定によりイソシアネート基の消失が確認されたので、フィルターで濾過して本発明の含フッ素ウレタンアクリレート(I´−2)200gを得た。含フッ素ウレタンアクリレート(I´−2)をGPCで測定した結果、数平均分子量516、重量平均分子量518であった。25℃の屈折率を測定した結果、1.446であった。また、フッ素含有率は、原料組成から計算した結果、21.3質量%であった。
<反射防止塗料組成物の調製>
中空シリカ微粒子(平均粒子径60nm)を20%含有するメチルイソブチルケトン分散液12.2部、含フッ素ウレタンアクリレート(I−1)2.0部、光重合開始剤として2−ヒドロキシ−1−{4−[4−(2−ヒドロキシ−2−メチル−プロピオニル)−ベンジル]−フェニル}−2−メチル−プロパン−1−オン(チバ・ジャパン株式会社製「イルガキュア127」)0.1部及び溶剤としてメチルイソブチルケトン85.7部を混合し溶解させて、本発明の反射防止塗料組成物(1)を調製した。反射防止塗料組成物(1)を用いて下記に示す方法にて反射防止フィルムを作成した。
5官能無黄変型ウレタンアクリレート50部、ジペンタエリスリトールヘキサアクリレート50部、酢酸ブチル25部、光重合開始剤として1−ヒドロキシシクロヘキシルフェニルケトン(チバスペシャリティーケミカルズ社製「イルガキュア184」)5部、溶剤としてトルエン54部、2−プロパノール28部、酢酸エチル28部及びプロピレングリコールモノメチルエーテル28部を混合し溶解させて、ハードコート層用塗料組成物を得た。
トライボギア HEIDON 往復磨耗試験機 TYPE:30S(新東科学株式会社製)を用いて、直径27mmの円形の治具にボンスター No,0000(日本スチールウール株式会社製)を取り付けた磨耗試験機(300g/cm2荷重)にて、10往復磨耗させて試験を行った。試験後の塗膜表面に付いた傷の本数を数えて、下記の基準によって耐擦傷性を評価した。
△:傷の本数が10本以上50本未満である。
×:傷の本数が50本以上である。
5℃正反射測定装置を備えた分光光度計(株式会社島津製作所製「UV−3100PC」)を用いて反射率の測定を行った。なお、反射率は波長550nm付近で極小値(最低反射率)となったときの値とした。
含フッ素ウレタンアクリレート(I−1)を2.0部用いる代わりに、含フッ素ウレタンアクリレート(I−2)〜含フッ素ウレタンアクリレート(I−3)を2.0部用いた以外は実施例1と同様にして反射防止塗料組成物(2)〜(3)を得た。実施例1と同様にして反射防止フィルム(2)〜(3)を得た。実施例1と同様にして反射防止フィルム(2)〜(3)上の反射防止塗料組成物の硬化塗膜表面について、耐擦傷性の評価を行うと共に、フィルムの反射率を測定した。評価結果を第1表に表す。
含フッ素ウレタンアクリレート(I−1)を2.0部の代わりに、比較対照用含フッ素ウレタンアクリレート(I´−1)〜比較対照用含フッ素ウレタンアクリレート(I´−2)を2.0部用いた以外は実施例1と同様にして比較対照用反射防止塗料組成物(1´)〜(2´)を得た。実施例1と同様にして比較対照用反射防止フィルム(1´)〜(2´)を得た。実施例1と同様にして比較対照用反射防止フィルム(1´)〜(2´)上の反射防止塗料組成物の硬化塗膜表面について、耐擦傷性の評価を行うと共に、フィルムの反射率を測定した。評価結果を第2表に表す。
Claims (10)
- 下記一般式(I)
で表され、且つ、フッ素原子の含有率が25〜60質量%であることを特徴とする含フッ素ウレタン(メタ)アクリレート。 - 前記フッ素原子の含有率が35〜60質量%である請求項1記載の含フッ素ウレタン(メタ)アクリレート。
- 前記R1、R2がそれぞれCnF2n+1CH2基(n=2〜6の整数)、CnF2n+1CH2CH2基(n=2〜6の整数)、またはC3F7OCF(CF3)CH2基である請求項1記載の含フッ素ウレタン(メタ)アクリレート。
- 前記R1、R2がそれぞれC6F13CH2CH2基またはC4F9CH2CH2基で、前記R3、R4がそれぞれ水素原子で、前記Aが前記構造式(A2)で表される連結基で、前記X、Yがそれぞれ前記(a)で表される連結基である請求項1記載の含フッ素ウレタン(メタ)アクリレート。
- 請求項1〜4のいずれか1項記載の含フッ素ウレタン(メタ)アクリレート(I)を含有することを特徴とする硬化性組成物。
- 反射防止塗料用途である、請求項5記載の硬化性組成物。
- 更に低屈折率剤(II)を含有する請求項6または請求項7記載の硬化性組成物。
- 前記低屈折率剤(II)が中空シリカ微粒子である請求項7記載の硬化性組成物。
- 請求項5〜8のいずれか1項記載の硬化性組成物の硬化塗膜を有することを特徴とする反射防止フィルム。
- 前記硬化塗膜の膜厚が50〜300nmである請求項9記載の反射防止フィルム。
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |