DE60015394T3 - Haftklebstoffe mit hohem brechungsindex - Google Patents
Haftklebstoffe mit hohem brechungsindex Download PDFInfo
- Publication number
- DE60015394T3 DE60015394T3 DE60015394T DE60015394T DE60015394T3 DE 60015394 T3 DE60015394 T3 DE 60015394T3 DE 60015394 T DE60015394 T DE 60015394T DE 60015394 T DE60015394 T DE 60015394T DE 60015394 T3 DE60015394 T3 DE 60015394T3
- Authority
- DE
- Germany
- Prior art keywords
- grams
- pressure
- sensitive adhesive
- monomer
- adhesive according
- 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.)
- Expired - Lifetime
Links
- 239000000853 adhesive Substances 0.000 title description 16
- 230000001070 adhesive effect Effects 0.000 title description 15
- 239000000178 monomer Substances 0.000 claims description 73
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 29
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 24
- -1 dibromo-substituted phenyl Chemical group 0.000 claims description 22
- 239000003431 cross linking reagent Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims description 4
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 claims description 4
- ABXIJVATUUDWEQ-UHFFFAOYSA-N 6-(2,4-dibromo-6-propan-2-ylphenoxy)hexyl prop-2-enoate Chemical compound CC(C)C1=CC(Br)=CC(Br)=C1OCCCCCCOC(=O)C=C ABXIJVATUUDWEQ-UHFFFAOYSA-N 0.000 claims description 4
- WNJWHQIMUOWKLD-UHFFFAOYSA-N 6-naphthalen-1-yloxyhexyl prop-2-enoate Chemical compound C1=CC=C2C(OCCCCCCOC(=O)C=C)=CC=CC2=C1 WNJWHQIMUOWKLD-UHFFFAOYSA-N 0.000 claims description 4
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003926 acrylamides Chemical class 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 4
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 4
- KWZHOXOMDFAEIY-UHFFFAOYSA-N (2,6-dibromo-4-dodecylphenyl) prop-2-enoate Chemical compound CCCCCCCCCCCCC1=CC(Br)=C(OC(=O)C=C)C(Br)=C1 KWZHOXOMDFAEIY-UHFFFAOYSA-N 0.000 claims description 3
- AEMSVTYSYDQNFR-UHFFFAOYSA-N (2,6-dibromo-4-nonylphenyl) prop-2-enoate Chemical compound CCCCCCCCCC1=CC(Br)=C(OC(=O)C=C)C(Br)=C1 AEMSVTYSYDQNFR-UHFFFAOYSA-N 0.000 claims description 3
- PQHAQYRBYAWNHV-UHFFFAOYSA-N 2-naphthalen-1-yloxyethyl prop-2-enoate Chemical compound C1=CC=C2C(OCCOC(=O)C=C)=CC=CC2=C1 PQHAQYRBYAWNHV-UHFFFAOYSA-N 0.000 claims description 3
- JHCYTKJAWFJIHL-UHFFFAOYSA-N 6-(2,4-dibromo-6-butan-2-ylphenoxy)hexyl prop-2-enoate Chemical compound CCC(C)C1=CC(Br)=CC(Br)=C1OCCCCCCOC(=O)C=C JHCYTKJAWFJIHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 claims description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 2
- 239000005968 1-Decanol Substances 0.000 claims description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 claims description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- OEXUTOBUVQBHCH-UHFFFAOYSA-N 2-naphthalen-2-yloxyethyl prop-2-enoate Chemical compound C1=CC=CC2=CC(OCCOC(=O)C=C)=CC=C21 OEXUTOBUVQBHCH-UHFFFAOYSA-N 0.000 claims description 2
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 claims description 2
- KHVSYYOPPZRKLM-UHFFFAOYSA-N 6-naphthalen-2-yloxyhexyl prop-2-enoate Chemical compound C1=CC=CC2=CC(OCCCCCCOC(=O)C=C)=CC=C21 KHVSYYOPPZRKLM-UHFFFAOYSA-N 0.000 claims description 2
- HVWJYTCIAJYLBV-UHFFFAOYSA-N 8-naphthalen-1-yloxyoctyl prop-2-enoate Chemical compound C1=CC=C2C(OCCCCCCCCOC(=O)C=C)=CC=CC2=C1 HVWJYTCIAJYLBV-UHFFFAOYSA-N 0.000 claims description 2
- OGMIVNPXPFPGBW-UHFFFAOYSA-N 8-naphthalen-2-yloxyoctyl prop-2-enoate Chemical compound C1=CC=CC2=CC(OCCCCCCCCOC(=O)C=C)=CC=C21 OGMIVNPXPFPGBW-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 2
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920006254 polymer film Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000011521 glass Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 20
- 239000008367 deionised water Substances 0.000 description 17
- 229910021641 deionized water Inorganic materials 0.000 description 17
- 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 16
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000003999 initiator Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- BUFSQBVYLWPJRX-UHFFFAOYSA-N ethyl 2-phenylsulfanylprop-2-enoate Chemical compound CCOC(=O)C(=C)SC1=CC=CC=C1 BUFSQBVYLWPJRX-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- PQJYXFVJBSRUPG-UHFFFAOYSA-N [3-(2-methylaziridine-1-carbonyl)phenyl]-(2-methylaziridin-1-yl)methanone Chemical compound CC1CN1C(=O)C1=CC=CC(C(=O)N2C(C2)C)=C1 PQJYXFVJBSRUPG-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 4
- 238000010382 chemical cross-linking Methods 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 230000004313 glare Effects 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- CDRUYNGFKORDOP-UHFFFAOYSA-N 2,4-dibromo-6-propan-2-ylphenol Chemical compound CC(C)C1=CC(Br)=CC(Br)=C1O CDRUYNGFKORDOP-UHFFFAOYSA-N 0.000 description 2
- JEGPPLVKZCYSRR-UHFFFAOYSA-N 2,6-dibromo-4-nonylphenol Chemical compound CCCCCCCCCC1=CC(Br)=C(O)C(Br)=C1 JEGPPLVKZCYSRR-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- KWWZHCSQVRVQGF-UHFFFAOYSA-N 2-phenylsulfanylethanol Chemical compound OCCSC1=CC=CC=C1 KWWZHCSQVRVQGF-UHFFFAOYSA-N 0.000 description 2
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 2
- GGEAHJULJQGRIQ-UHFFFAOYSA-N 6-(2,4-dibromo-6-propan-2-ylphenoxy)hexan-1-ol Chemical compound CC(C)C1=CC(Br)=CC(Br)=C1OCCCCCCO GGEAHJULJQGRIQ-UHFFFAOYSA-N 0.000 description 2
- UAGGAZHJHUTMJP-UHFFFAOYSA-N 6-naphthalen-1-yloxyhexan-1-ol Chemical compound C1=CC=C2C(OCCCCCCO)=CC=CC2=C1 UAGGAZHJHUTMJP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004971 Cross linker Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 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 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000008378 aryl ethers Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
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- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
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- 238000010557 suspension polymerization reaction Methods 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
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- 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
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- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
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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
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
-
- 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
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US605500 | 1995-09-22 | ||
| PCT/US1999/025276 WO2001030872A1 (en) | 1999-10-28 | 1999-10-28 | Compositions and articles made therefrom |
| WOPCT/US99/25276 | 1999-10-28 | ||
| US09/605,500 US6663978B1 (en) | 2000-06-28 | 2000-06-28 | High refractive index pressure-sensitive adhesives |
| PCT/US2000/021817 WO2001030933A1 (en) | 1999-10-28 | 2000-08-10 | High refractive index pressure-sensitive adhesives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE60015394D1 DE60015394D1 (de) | 2004-12-02 |
| DE60015394T2 DE60015394T2 (de) | 2005-10-27 |
| DE60015394T3 true DE60015394T3 (de) | 2009-04-16 |
Family
ID=26795854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60015394T Expired - Lifetime DE60015394T3 (de) | 1999-10-28 | 2000-08-10 | Haftklebstoffe mit hohem brechungsindex |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1244756B2 (https=) |
| JP (2) | JP4943611B2 (https=) |
| KR (1) | KR100707745B1 (https=) |
| CA (1) | CA2386847A1 (https=) |
| DE (1) | DE60015394T3 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4640740B2 (ja) * | 2000-12-04 | 2011-03-02 | 日東電工株式会社 | 感圧性接着剤組成物、感圧性接着シート及び光学フィルム |
| JP4641628B2 (ja) * | 2001-01-23 | 2011-03-02 | 日本化薬株式会社 | 接着剤組成物、光ディスク用接着剤組成物及びその硬化物。 |
| EP1956064B1 (en) | 2005-11-21 | 2010-10-13 | Soken Chemical & Engineering Co. Ltd., | Adhesive composition for optical film, adhesive sheet, and optical member using such adhesive composition |
| KR100932888B1 (ko) * | 2006-07-21 | 2009-12-21 | 주식회사 엘지화학 | 광학 보상된 아크릴계 점착제 조성물, 이를 포함하는편광판 및 액정표시소자 |
| KR100775440B1 (ko) * | 2006-12-20 | 2007-11-12 | 동우신테크 주식회사 | 리세드로네이트 나트륨 헤미펜타히드레이트의 제조방법 |
| JP5493158B2 (ja) * | 2007-06-19 | 2014-05-14 | サイデン化学株式会社 | 光学用粘着剤組成物および光学機能性フィルム |
| US8378046B2 (en) | 2007-10-19 | 2013-02-19 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US8309650B2 (en) | 2007-10-30 | 2012-11-13 | 3M Innovative Properties Company | High refractive index adhesives |
| JP5649274B2 (ja) * | 2007-11-07 | 2015-01-07 | 日本合成化学工業株式会社 | 偏光板用粘着剤及び粘着剤層付き偏光板 |
| JP5362291B2 (ja) * | 2008-08-26 | 2013-12-11 | 日東電工株式会社 | アクリル系粘着剤組成物、アクリル系粘着剤層およびアクリル系粘着テープ又はシート |
| WO2010118421A1 (en) * | 2009-04-10 | 2010-10-14 | Pixeloptics, Inc. | Curable adhesive compositions |
| JP5729973B2 (ja) * | 2010-11-11 | 2015-06-03 | 日本合成化学工業株式会社 | アクリル系粘着剤、光学部材用粘着剤、粘着剤層付き光学部材、画像表示装置 |
| JP5524640B2 (ja) * | 2010-01-26 | 2014-06-18 | 大王製紙株式会社 | 粘着シート |
| JP5318025B2 (ja) * | 2010-04-14 | 2013-10-16 | 日東電工株式会社 | 液晶パネルへの光学フィルム貼着固定用感圧性接着剤組成物及び感圧性接着シート、並びに光学フィルム |
| JP5517716B2 (ja) * | 2010-04-14 | 2014-06-11 | 日東電工株式会社 | 導電性フィルム用感圧性接着剤組成物及び感圧性接着シート、並びに導電性フィルム |
| JP2012021148A (ja) * | 2010-06-16 | 2012-02-02 | Nippon Synthetic Chem Ind Co Ltd:The | 粘着剤、光学部材用粘着剤、粘着剤層付き光学部材、画像表示装置 |
| US9074040B2 (en) | 2010-12-20 | 2015-07-07 | Mitsui Chemicals, Inc. | Curable adhesive compositions |
| US10202477B2 (en) | 2012-12-28 | 2019-02-12 | 3M Innovative Properties Company | Optically clear hot melt processable high refractive index adhesives |
| JP6216519B2 (ja) * | 2013-03-04 | 2017-10-18 | リンテック株式会社 | 粘着性組成物、粘着剤および粘着シート |
| JP6066937B2 (ja) * | 2014-01-28 | 2017-01-25 | 藤森工業株式会社 | 光拡散粘着剤層、及び光拡散粘着フィルム |
| JP2017193595A (ja) * | 2016-04-18 | 2017-10-26 | 日東電工株式会社 | 透明難燃テープおよび難燃性構造体 |
| JP6717884B2 (ja) * | 2018-07-05 | 2020-07-08 | 藤森工業株式会社 | 粘着剤層、及び粘着フィルム |
| JP6644129B2 (ja) * | 2018-12-27 | 2020-02-12 | 藤森工業株式会社 | 粘着剤層、及び粘着フィルム |
| KR20250162956A (ko) * | 2020-03-24 | 2025-11-19 | 닛토덴코 가부시키가이샤 | 점착제 조성물, 점착제 및 점착 시트 |
| JP7690305B2 (ja) * | 2020-03-24 | 2025-06-10 | 日東電工株式会社 | 粘着剤組成物、粘着剤および粘着シート |
| JP7092823B2 (ja) * | 2020-04-07 | 2022-06-28 | 藤森工業株式会社 | 粘着剤層、及び粘着フィルム |
| CN112898475B (zh) * | 2021-01-21 | 2022-01-25 | 西南石油大学 | 一种两亲性沥青质抑制剂及其制备方法 |
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| NL270084A (https=) † | 1960-10-10 | 1900-01-01 | ||
| JPS58186277A (ja) * | 1982-04-26 | 1983-10-31 | Victor Co Of Japan Ltd | デイジタル信号記録方式 |
| JPH0230353B2 (ja) † | 1982-05-11 | 1990-07-05 | Kanzaki Paper Mfg Co Ltd | Kanatsusetsuchakuzaisoseibutsu |
| JPS59111114A (ja) * | 1982-12-16 | 1984-06-27 | Sekisui Chem Co Ltd | 接着層を有する偏光板 |
| DE3321502C2 (de) † | 1983-06-15 | 1985-05-30 | Chemische Werke Hüls AG, 4370 Marl | Polymere Ester der Acrylsäure und Methacrylsäure mit aromatischen Thioetheralkoholen und Verfahren zu ihrer Herstellung |
| JPH01278518A (ja) * | 1988-04-28 | 1989-11-08 | Shinnakamura Kagaku Kogyo Kk | 感圧性接着剤用組成物 |
| JPH02248482A (ja) * | 1989-03-23 | 1990-10-04 | Fujikura Kasei Co Ltd | 光硬化性感圧接着剤組成物 |
| JPH0331309A (ja) * | 1989-06-27 | 1991-02-12 | Matsushita Electric Works Ltd | 高屈折率樹脂作製用組成物 |
| JPH04264178A (ja) * | 1991-02-18 | 1992-09-18 | Nissei Kagaku Kogyosho:Kk | 透明材料用の光硬化型接着剤組成物 |
| JP3498157B2 (ja) † | 1994-06-01 | 2004-02-16 | 綜研化学株式会社 | 液晶素子用感圧接着剤組成物および液晶素子 |
| JP3775760B2 (ja) * | 1995-04-28 | 2006-05-17 | 日本化薬株式会社 | 紫外線硬化型接着剤組成物、硬化物、物品及び接着方法 |
| CN1097080C (zh) * | 1995-06-26 | 2002-12-25 | 美国3M公司 | 光漫射粘合剂 |
| JPH09111189A (ja) * | 1995-10-18 | 1997-04-28 | Sumitomo Seika Chem Co Ltd | 光学接着剤用組成物 |
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| JP4578625B2 (ja) * | 1999-06-10 | 2010-11-10 | 電気化学工業株式会社 | 硬化性樹脂組成物、接着剤組成物、接合体及び接着方法 |
-
2000
- 2000-08-10 EP EP00957357A patent/EP1244756B2/en not_active Expired - Lifetime
- 2000-08-10 JP JP2001533919A patent/JP4943611B2/ja not_active Expired - Fee Related
- 2000-08-10 CA CA002386847A patent/CA2386847A1/en not_active Abandoned
- 2000-08-10 DE DE60015394T patent/DE60015394T3/de not_active Expired - Lifetime
- 2000-08-10 KR KR1020027005385A patent/KR100707745B1/ko not_active Expired - Fee Related
-
2011
- 2011-12-28 JP JP2011289641A patent/JP2012107246A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE60015394T2 (de) | 2005-10-27 |
| JP2003535921A (ja) | 2003-12-02 |
| KR100707745B1 (ko) | 2007-04-17 |
| DE60015394D1 (de) | 2004-12-02 |
| EP1244756B1 (en) | 2004-10-27 |
| EP1244756B2 (en) | 2008-08-20 |
| JP4943611B2 (ja) | 2012-05-30 |
| EP1244756A1 (en) | 2002-10-02 |
| JP2012107246A (ja) | 2012-06-07 |
| CA2386847A1 (en) | 2001-05-03 |
| KR20020082830A (ko) | 2002-10-31 |
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| 8363 | Opposition against the patent | ||
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