JP5596549B2 - 高屈折率接着剤 - Google Patents
高屈折率接着剤 Download PDFInfo
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- JP5596549B2 JP5596549B2 JP2010532106A JP2010532106A JP5596549B2 JP 5596549 B2 JP5596549 B2 JP 5596549B2 JP 2010532106 A JP2010532106 A JP 2010532106A JP 2010532106 A JP2010532106 A JP 2010532106A JP 5596549 B2 JP5596549 B2 JP 5596549B2
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- adhesive
- weight
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- meth
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- 239000000853 adhesive Substances 0.000 title claims description 86
- 230000001070 adhesive effect Effects 0.000 title claims description 86
- 239000000178 monomer Substances 0.000 claims description 112
- 239000002253 acid Substances 0.000 claims description 30
- 229920001577 copolymer Polymers 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 239000004014 plasticizer Substances 0.000 claims description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 description 37
- -1 Polyethylene terephthalate Polymers 0.000 description 31
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 14
- 239000004971 Cross linker Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- 238000000576 coating method Methods 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
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- 150000003254 radicals Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
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- 238000002310 reflectometry Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 4
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 230000004313 glare Effects 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 4
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 150000001716 carbazoles Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 150000003009 phosphonic acids Chemical class 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 239000005968 1-Decanol Substances 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- MCRZWYDXIGCFKO-UHFFFAOYSA-N 2-butylpropanedioic acid Chemical compound CCCCC(C(O)=O)C(O)=O MCRZWYDXIGCFKO-UHFFFAOYSA-N 0.000 description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- KCFHXVCGEQRWDQ-UHFFFAOYSA-N 6-carbazol-9-ylhexan-1-ol Chemical compound C1=CC=C2N(CCCCCCO)C3=CC=CC=C3C2=C1 KCFHXVCGEQRWDQ-UHFFFAOYSA-N 0.000 description 2
- YCDZLMZEVBWFHB-UHFFFAOYSA-N 8-carbazol-9-yloctan-1-ol Chemical compound C1=CC=C2N(CCCCCCCCO)C3=CC=CC=C3C2=C1 YCDZLMZEVBWFHB-UHFFFAOYSA-N 0.000 description 2
- RQFLRWKDRQNACO-UHFFFAOYSA-N 8-carbazol-9-yloctyl prop-2-enoate Chemical compound C1=CC=C2N(CCCCCCCCOC(=O)C=C)C3=CC=CC=C3C2=C1 RQFLRWKDRQNACO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PQJYXFVJBSRUPG-UHFFFAOYSA-N [3-(2-methylaziridine-1-carbonyl)phenyl]-(2-methylaziridin-1-yl)methanone Chemical group CC1CN1C(=O)C1=CC=CC(C(=O)N2C(C2)C)=C1 PQJYXFVJBSRUPG-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 description 2
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 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
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98373507P | 2007-10-30 | 2007-10-30 | |
| US60/983,735 | 2007-10-30 | ||
| PCT/US2008/078740 WO2009058513A1 (en) | 2007-10-30 | 2008-10-03 | High refractive index adhesives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011502202A JP2011502202A (ja) | 2011-01-20 |
| JP2011502202A5 JP2011502202A5 (enExample) | 2011-11-24 |
| JP5596549B2 true JP5596549B2 (ja) | 2014-09-24 |
Family
ID=40276093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010532106A Expired - Fee Related JP5596549B2 (ja) | 2007-10-30 | 2008-10-03 | 高屈折率接着剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8309650B2 (enExample) |
| EP (1) | EP2207860B1 (enExample) |
| JP (1) | JP5596549B2 (enExample) |
| KR (1) | KR101545365B1 (enExample) |
| CN (1) | CN101910348B (enExample) |
| WO (1) | WO2009058513A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160105527A (ko) | 2008-07-10 | 2016-09-06 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 점탄성 도광체 |
| KR101578250B1 (ko) | 2008-07-10 | 2015-12-16 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 점탄성 도광체를 갖는 재귀반사성 용품 및 장치 |
| EP2310885B1 (en) * | 2008-07-10 | 2017-03-29 | 3M Innovative Properties Company | Retroreflective articles and devices having viscoelastic lightguide |
| CN107037526A (zh) | 2008-08-08 | 2017-08-11 | 3M创新有限公司 | 具有粘弹性层的用于控制光的光导 |
| BR112012003740A2 (pt) | 2009-08-21 | 2020-08-11 | 3M Innovantive Properties Company | kits e compósitos de distribuição de tensão |
| BR112012003745A2 (pt) | 2009-08-21 | 2019-09-24 | 3M Innovantive Properties Company | métodos e produtos para iluminação de tecidos |
| WO2011022527A1 (en) | 2009-08-21 | 2011-02-24 | 3M Innovative Properties Company | Methods and products for reducing tissue trauma using water-resistant stress-distributing materials |
| US20130011608A1 (en) | 2010-01-13 | 2013-01-10 | Wolk Martin B | Optical films with microstructured low refractive index nanovoided layers and methods therefor |
| KR20120115568A (ko) | 2010-02-10 | 2012-10-18 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 점탄성 층을 구비한 조명 장치 |
| CN103154788B (zh) | 2010-10-11 | 2015-08-19 | 3M创新有限公司 | 具有粘弹性光导的照明装置 |
| WO2012054318A1 (en) | 2010-10-20 | 2012-04-26 | 3M Innovative Properties Company | Wide band semi-specular mirror film incorporating nanovoided polymeric layer |
| TWI465534B (zh) * | 2010-12-31 | 2014-12-21 | Eternal Materials Co Ltd | 可光固化之黏著組合物 |
| KR101985030B1 (ko) | 2011-05-25 | 2019-05-31 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 광 제어 필름 |
| WO2013148506A1 (en) | 2012-03-30 | 2013-10-03 | 3M Innovative Properties Company | Urea-based and urethane-based pressure sensitive adhesive blends |
| EP2864285B1 (en) | 2012-06-21 | 2016-10-19 | Council of Scientific & Industrial Research | High refractive index (meth)acrylates |
| US9477354B2 (en) | 2012-11-16 | 2016-10-25 | 3M Innovative Properties Company | Conductive trace hiding materials, articles, and methods |
| JP6155903B2 (ja) * | 2013-03-14 | 2017-07-05 | 日本ゼオン株式会社 | 光学部材用粘着剤組成物及び光学部材用粘着層 |
| JP5713155B1 (ja) * | 2013-11-29 | 2015-05-07 | Dic株式会社 | 光硬化性光学接着剤組成物、その硬化物、及び液晶表示装置 |
| US9904001B2 (en) | 2014-03-18 | 2018-02-27 | 3M Innovative Properties Company | Marketing strip with viscoelastic lightguide |
| CN106084867A (zh) * | 2016-06-08 | 2016-11-09 | 中国船舶重工集团公司第七二五研究所 | 一种用于高温域的高阻尼粘弹性复合材料及其制备方法 |
| EP3715432A1 (en) * | 2019-03-27 | 2020-09-30 | 3M Innovative Properties Company | Pressure-sensitive adhesive composition with transparency characteristics |
| US20220112321A1 (en) * | 2020-10-09 | 2022-04-14 | Rohm And Haas Electronic Materials Llc | High refractive index materials |
| CN114133877B (zh) * | 2021-12-10 | 2024-03-29 | 西安思摩威新材料有限公司 | 一种含大共轭芳香环丙烯酸化合物单体的光固化组合物胶水及其使用方法和应用 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB959775A (en) | 1959-08-03 | 1964-06-03 | Rohm & Haas | Copolymers and coating compositions thereof |
| US3691140A (en) * | 1970-03-09 | 1972-09-12 | Spencer Ferguson Silver | Acrylate copolymer microspheres |
| US4166152B1 (en) * | 1977-08-17 | 1999-05-18 | Minnesota Mining & Mfg | Tacky polymeric microspheres |
| DE3376267D1 (de) * | 1982-11-11 | 1988-05-19 | Showa Denko Kk | Polymerizable compositions |
| DE3479651D1 (en) | 1983-05-20 | 1989-10-12 | Showa Denko Kk | Naphthalene derivative, polymerizable composition containing the same and polymer obtainable by polymerizing this composition |
| US4619979A (en) * | 1984-03-28 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Continuous free radial polymerization in a wiped-surface reactor |
| US4843134A (en) * | 1984-03-28 | 1989-06-27 | Minnesota Mining And Manufacturing Company | Acrylate pressure-sensitive adhesives containing insolubles |
| GB2170427B (en) * | 1985-02-01 | 1989-06-07 | Sanyo Kokusaku Pulp Co | Pressure-sensitive adhesive tapes or sheets |
| US4656218A (en) * | 1985-02-08 | 1987-04-07 | Sanyo Kokusaku Pulp Co., Ltd. | Adhesive copolymer microspheres-containing aqueous suspension and method for producing the same |
| US4737559A (en) * | 1986-05-19 | 1988-04-12 | Minnesota Mining And Manufacturing Co. | Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers |
| US5045569A (en) * | 1988-11-30 | 1991-09-03 | Minnesota Mining And Manufacturing Company | Hollow acrylate polymer microspheres |
| DE3906245A1 (de) * | 1989-02-28 | 1990-09-06 | Basf Ag | Seitenstaendige carbazolyl-gruppen enthaltende poly(meth)acrylate und elektrophotographische aufzeichnungselemente, enthaltend dieselben |
| DE3906246A1 (de) * | 1989-02-28 | 1990-09-06 | Basf Ag | Verfahren zur herstellung carbazolsubstituierter polyacrylate oder polymethacrylate, die so hergestellten produkte und ihre verwendung |
| US5110971A (en) * | 1989-07-05 | 1992-05-05 | Aristech Chemical Corporation | Silyl derivatives of eugenol |
| JPH0670209B2 (ja) * | 1989-11-14 | 1994-09-07 | 株式会社総合歯科医療研究所 | 光学用接着剤 |
| AU634338B2 (en) * | 1990-02-08 | 1993-02-18 | Mitsubishi Rayon Company Limited | Composition for plastic lenses |
| JPH041207A (ja) * | 1990-04-19 | 1992-01-06 | Canon Inc | 光重合性樹脂組成物および記録媒体 |
| FR2665452B1 (fr) * | 1990-07-31 | 1992-10-09 | Thomson Csf | Copolymeres amorphes pour composes photorefractifs utilises dans le traitement du signal optique. |
| US5290892A (en) * | 1990-11-07 | 1994-03-01 | Nestle S.A. | Flexible intraocular lenses made from high refractive index polymers |
| JP3228977B2 (ja) * | 1991-03-14 | 2001-11-12 | ジョーンズ・マンヴィル・インターナショナル・インコーポレーテッド | カルボジイミド変性ポリエステル繊維およびその製造方法 |
| JPH0558950A (ja) * | 1991-06-21 | 1993-03-09 | Nippon Kayaku Co Ltd | （メタ）アクリル酸エステル |
| US5132430A (en) * | 1991-06-26 | 1992-07-21 | Polaroid Corporation | High refractive index polymers |
| JP3397448B2 (ja) | 1994-05-30 | 2003-04-14 | 日本化薬株式会社 | 紫外線硬化型透過型スクリーン用樹脂組成物及びその硬化物 |
| US5804610A (en) * | 1994-09-09 | 1998-09-08 | Minnesota Mining And Manufacturing Company | Methods of making packaged viscoelastic compositions |
| US6254712B1 (en) * | 1998-12-08 | 2001-07-03 | Avery Dennison Corporation | Extrusion coating process for making high transparency protective and decorative films |
| EP0835294B1 (en) * | 1995-06-26 | 2003-01-29 | Minnesota Mining And Manufacturing Company | Light diffusing adhesive |
| US5905099A (en) * | 1995-11-06 | 1999-05-18 | Minnesota Mining And Manufacturing Company | Heat-activatable adhesive composition |
| US5637646A (en) * | 1995-12-14 | 1997-06-10 | Minnesota Mining And Manufacturing Company | Bulk radical polymerization using a batch reactor |
| JPH09272707A (ja) | 1996-04-04 | 1997-10-21 | Toagosei Co Ltd | 活性エネルギー線硬化型（メタ）アクリレート組成物 |
| US6207260B1 (en) * | 1998-01-13 | 2001-03-27 | 3M Innovative Properties Company | Multicomponent optical body |
| US6013722A (en) * | 1998-01-27 | 2000-01-11 | 3M Innovative Properties Company | Non-whitening emulsion pressure sensitive adhesives |
| EP1035142A1 (en) * | 1999-03-09 | 2000-09-13 | Nidek Co., Ltd. | Acrylic copolymer materials suitable for ophthalmic devices |
| US6663978B1 (en) * | 2000-06-28 | 2003-12-16 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US7166686B2 (en) * | 2000-06-28 | 2007-01-23 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US6663820B2 (en) | 2001-03-14 | 2003-12-16 | The Procter & Gamble Company | Method of manufacturing microneedle structures using soft lithography and photolithography |
| US6703463B2 (en) * | 2001-08-01 | 2004-03-09 | Avery Dennison Corporation | Optical adhesive coating having low refractive index |
| WO2003046030A1 (de) | 2001-11-24 | 2003-06-05 | Tesa Ag | Vernetzung von photoinitiator-initialisierten polyacrylaten |
| US6864338B2 (en) * | 2002-02-26 | 2005-03-08 | Nitto Denko Corporation | Sterically regulated methacrylic polymer and process for producing the same |
| JP2003321516A (ja) * | 2002-02-26 | 2003-11-14 | Nitto Denko Corp | 立体制御型メタクリル系重合体およびその製造方法 |
| DE10221093A1 (de) * | 2002-05-11 | 2003-11-20 | Tesa Ag | Verwendung von Makromonomeren für die Herstellung von Acrylathaftklebemassen |
| US6893718B2 (en) * | 2002-05-20 | 2005-05-17 | 3M Innovative Properties Company | Pressure sensitive adhesive composition, articles made therewith and method of use |
| JP2004323557A (ja) | 2003-04-21 | 2004-11-18 | Toagosei Co Ltd | 硬化型組成物及びその硬化物 |
| DE10322899A1 (de) * | 2003-05-21 | 2004-12-16 | Tesa Ag | UV-transparente Haftklebemasse |
| US6842288B1 (en) * | 2003-10-30 | 2005-01-11 | 3M Innovative Properties Company | Multilayer optical adhesives and articles |
| JP2005272773A (ja) | 2004-03-26 | 2005-10-06 | Toagosei Co Ltd | 活性エネルギー線硬化型光学材料用組成物 |
| WO2005116165A1 (ja) * | 2004-05-31 | 2005-12-08 | Dainippon Ink And Chemicals, Inc. | 重合性液晶組成物及び光学異方体 |
| JP4385997B2 (ja) | 2004-05-31 | 2009-12-16 | Ｄｉｃ株式会社 | 重合性液晶組成物及び光学異方体 |
| JP2006124500A (ja) * | 2004-10-28 | 2006-05-18 | Emulsion Technology Co Ltd | 光硬化性接着剤組成物およびその製造方法 |
| DE102005054781A1 (de) * | 2005-11-15 | 2007-05-16 | Tesa Ag | Verwendung eines doppelseitigen Haftklebebandes zur Verklebung bei der Herstellung von Elektronikartikel |
| US7825189B2 (en) | 2005-11-21 | 2010-11-02 | Soken Chemical & Engineering Co., Ltd. | Adhesive composition for optical film, adhesive sheet, and optical member using such adhesive composition |
| DE102006044718A1 (de) | 2006-09-20 | 2008-04-03 | Tesa Ag | Klebemasse |
| US20080221291A1 (en) * | 2007-03-07 | 2008-09-11 | 3M Innovative Properties Company | Microstructured optical films comprising biphenyl difunctional monomers |
-
2008
- 2008-10-03 KR KR1020107011775A patent/KR101545365B1/ko not_active Expired - Fee Related
- 2008-10-03 US US12/738,090 patent/US8309650B2/en not_active Expired - Fee Related
- 2008-10-03 JP JP2010532106A patent/JP5596549B2/ja not_active Expired - Fee Related
- 2008-10-03 WO PCT/US2008/078740 patent/WO2009058513A1/en not_active Ceased
- 2008-10-03 CN CN200880122445XA patent/CN101910348B/zh not_active Expired - Fee Related
- 2008-10-03 EP EP08843534.2A patent/EP2207860B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011502202A (ja) | 2011-01-20 |
| EP2207860B1 (en) | 2016-02-10 |
| KR101545365B1 (ko) | 2015-08-18 |
| US20100222496A1 (en) | 2010-09-02 |
| WO2009058513A1 (en) | 2009-05-07 |
| CN101910348A (zh) | 2010-12-08 |
| US8309650B2 (en) | 2012-11-13 |
| CN101910348B (zh) | 2013-07-03 |
| EP2207860A1 (en) | 2010-07-21 |
| KR20100101588A (ko) | 2010-09-17 |
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