EP0716673A1 - Self-adhesive film and laminate using the same - Google Patents
Self-adhesive film and laminate using the sameInfo
- Publication number
- EP0716673A1 EP0716673A1 EP94924476A EP94924476A EP0716673A1 EP 0716673 A1 EP0716673 A1 EP 0716673A1 EP 94924476 A EP94924476 A EP 94924476A EP 94924476 A EP94924476 A EP 94924476A EP 0716673 A1 EP0716673 A1 EP 0716673A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oligomer
- self
- monomer
- adhesive film
- acrylic acid
- 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.)
- Ceased
Links
- 239000002313 adhesive film Substances 0.000 title claims abstract description 32
- 239000000178 monomer Substances 0.000 claims abstract description 32
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920001519 homopolymer Polymers 0.000 claims abstract description 11
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 10
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 description 17
- 239000000853 adhesive Substances 0.000 description 14
- 230000001070 adhesive effect Effects 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 229920002799 BoPET Polymers 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000000428 dust Substances 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- -1 urethane compound Chemical class 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 4
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007970 homogeneous dispersion Substances 0.000 description 2
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GOUZWCLULXUQSR-UHFFFAOYSA-N (2-chlorophenyl) prop-2-enoate Chemical compound ClC1=CC=CC=C1OC(=O)C=C GOUZWCLULXUQSR-UHFFFAOYSA-N 0.000 description 1
- UGRXGEHQNPBILJ-UHFFFAOYSA-N (2-methoxyphenyl) prop-2-enoate Chemical compound COC1=CC=CC=C1OC(=O)C=C UGRXGEHQNPBILJ-UHFFFAOYSA-N 0.000 description 1
- VHRJYXSVRKBCEX-UHFFFAOYSA-N (2-tert-butylphenyl) prop-2-enoate Chemical compound CC(C)(C)C1=CC=CC=C1OC(=O)C=C VHRJYXSVRKBCEX-UHFFFAOYSA-N 0.000 description 1
- OJNXPAPLAAGFBJ-UHFFFAOYSA-N (4-methylphenyl) prop-2-enoate Chemical compound CC1=CC=C(OC(=O)C=C)C=C1 OJNXPAPLAAGFBJ-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- KUGVQHLGVGPAIZ-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-henicosafluorodecan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KUGVQHLGVGPAIZ-UHFFFAOYSA-N 0.000 description 1
- SUDVPELGFZKOMD-UHFFFAOYSA-N 1,2-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(C(C)C)C(C(C)C)=CC=C3SC2=C1 SUDVPELGFZKOMD-UHFFFAOYSA-N 0.000 description 1
- DPAVORBDLHTGCY-UHFFFAOYSA-N 1,2-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3SC2=C1 DPAVORBDLHTGCY-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- IKZYSJAHCZYFHH-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)(F)C(F)F IKZYSJAHCZYFHH-UHFFFAOYSA-N 0.000 description 1
- RSVZYSKAPMBSMY-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)F RSVZYSKAPMBSMY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- PTJDGKYFJYEAOK-UHFFFAOYSA-N 2-butoxyethyl prop-2-enoate Chemical compound CCCCOCCOC(=O)C=C PTJDGKYFJYEAOK-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- LRRQSCPPOIUNGX-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(O)C(=O)C1=CC=C(OC)C=C1 LRRQSCPPOIUNGX-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- ZOZMYZRPPLNSJX-UHFFFAOYSA-N 2-nitroso-9h-fluorene;(phenyldisulfanyl)benzene Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1.C1=CC=C2C3=CC=C(N=O)C=C3CC2=C1 ZOZMYZRPPLNSJX-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UACBZRBYLSMNGV-UHFFFAOYSA-N 3-ethoxypropyl prop-2-enoate Chemical compound CCOCCCOC(=O)C=C UACBZRBYLSMNGV-UHFFFAOYSA-N 0.000 description 1
- NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 description 1
- LHEKBWMWMVRJMO-UHFFFAOYSA-N 3-methoxypropyl prop-2-enoate Chemical compound COCCCOC(=O)C=C LHEKBWMWMVRJMO-UHFFFAOYSA-N 0.000 description 1
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- GBJVVSCPOBPEIT-UHFFFAOYSA-N AZT-1152 Chemical compound N=1C=NC2=CC(OCCCN(CC)CCOP(O)(O)=O)=CC=C2C=1NC(=NN1)C=C1CC(=O)NC1=CC=CC(F)=C1 GBJVVSCPOBPEIT-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000004830 Super Glue Substances 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- AQNSVANSEBPSMK-UHFFFAOYSA-N dicyclopentenyl methacrylate Chemical compound C12CC=CC2C2CC(OC(=O)C(=C)C)C1C2.C12C=CCC2C2CC(OC(=O)C(=C)C)C1C2 AQNSVANSEBPSMK-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- SZPUDSQPVUIVKC-UHFFFAOYSA-N ethoxymethyl prop-2-enoate Chemical compound CCOCOC(=O)C=C SZPUDSQPVUIVKC-UHFFFAOYSA-N 0.000 description 1
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- MCVIJOHIRQEVKV-UHFFFAOYSA-N ethyl 2-prop-2-enoyloxybenzoate Chemical compound CCOC(=O)C1=CC=CC=C1OC(=O)C=C MCVIJOHIRQEVKV-UHFFFAOYSA-N 0.000 description 1
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 description 1
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- IDGSKUCYENSHAA-UHFFFAOYSA-N formic acid;2-hydroxy-1-(2-methylphenyl)-2-phenylethanone Chemical compound OC=O.CC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 IDGSKUCYENSHAA-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PZDUWXKXFAIFOR-UHFFFAOYSA-N hexadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C=C PZDUWXKXFAIFOR-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- HRNCZFIWELTICZ-UHFFFAOYSA-N methyl 2-prop-2-enoyloxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC(=O)C=C HRNCZFIWELTICZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- NWAHZAIDMVNENC-UHFFFAOYSA-N octahydro-1h-4,7-methanoinden-5-yl methacrylate Chemical compound C12CCCC2C2CC(OC(=O)C(=C)C)C1C2 NWAHZAIDMVNENC-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
Definitions
- the self-adhesive film has substantially no surface tackiness.
- the "self-adhesive film” herein referred to means a film-like adhesive capable of imparting a high adhesion strength by being self-contacted and pressed.
- Japanese Unexamined Patent Publication (Kokai) No. 2-102282 discloses a self- adhesive material formed by applying a pressure-sensitive adhesive onto a base material.
- this pressure-sensitive adhesive is tacky.
- Japanese Unexamined Patent Publication (Kokai) No. 2-6578 discloses a self-fusion-bonding tape prepared by mixing uncrosslinked rubber and crosslinked rubber.
- this tape is self-contacted and allowed to stand for a predetermined period of time, so as to be integrated, cohesive failure results when the adhered parts are debonded. It is, therefore, impossible to use the tape again.
- this tape requires a long period of time in order to obtain a sufficient adhesion strength.
- Japanese Unexamined Patent Publication (Kokai) No. 1-138280 discloses a self-adhesive tape having an adhesive layer obtained by adding a tackifier to a styrene-ethylene-butylene-styrene copolymer. Although the coated surfaces of this self-adhesive tape are adhered under a slight pressure, this tape does not adhere to the surfaces of many other articles, even to a smooth surface such as that of stainless steel, even if a high pressure is applied. In addition, since this adhesive layer is of an uncrosslinked type, it dissolves when it comes into contact with a solvent. Furthermore, the adhesive layer is applied to a base material, from a solvent solution of the adhesive.
- At least 3 components should be added. Accordingly, in this high molecular weight material, it has been observed that homogeneous dispersion and mixing are comparatively difficult to achieve. When a homogeneous dispersion is not achieved, irregular adhesion strengths frequently result.
- the present invention provides a self-adhesive film made of a simple and inexpensive material, which has little or no surface tackiness, which is unlikely to be contaminated with dust and which causes no cohesive failure, even when parts of a same film are adhered to each other and thereafter debonded.
- the film of the invention is repeatedly usable.
- the present invention also provides an adhesive laminate prepared by use of such a self- adhesive film.
- the present invention provides a film having no or little surface tackiness.
- the film comprises a copolymer of (A) at least one (meth)acrylic acid ester monomer and (B) at least one (meth)acrylic acid ester oligomer.
- Oligomer (B) contains a reactive functional group. Preferably, this group is a radiation polymerizable group.
- the glass transition temperature of a homopolymer derived from monomer (A) has a Tg of greater than 20°C.
- the glass transition temperature of oligomer (B) is less than -20°C.
- a film of the copolymer resulting from the polymerization of monomer (A) and oligomer (B) preferably has a glass transition of from 0-60°C. When expressed in terms of the Fox equation, the copolymer film has an F value of from about 2.8 x 10 "3 to 3.7 x 10 "3 .
- Tg, Tg 2 ... Tg n denote the respective glass transition temperatures (in °C) of each of the first to the n-th components of the polymer prepared from monomer (A) and oligomer (B).
- the present invention provides a self-adhesive film which is not easily contaminated with dust and the like owing to the absence of tackiness.
- the film can repeatedly be used because no cohesive failure is caused even if the crosslinked films are adhered and then debonded.
- the film is excellent in weather (light) resistance and water resistance, and can be prepared from a simple and inexpensive material.
- Fig. 1 is a perspective view of a handle-bearing sample with the applied self-adhesive film of the invention as prepared in Example 1 hereinafter.
- Fig. 2 is a graph showing the change of the self-adhesive strength (0 degree peel strength) of the self-adhesive film of the present invention as contrasted to the compositions of the oligomer and monomer of the present film.
- Fig. 3 is a graph showing the change of the self-adhesion strength (0 degree peel strength) of the self-adhesive film of the present invention as contrasted to the thickness of the present film.
- Examples of useful (meth)acrylic acid ester monomers useful as monomer (A) materials include tert-butyl acrylate, isobornyl acrylate, dicyclopentenyl acrylate, 2-t-butylphenyl acrylate, 2-naphthyl acrylate, methoxyphenyl acrylate, n-hexadecyl acrylate, dicyclopentenyl acrylate, 2- methoxycarbonylphenyl acrylate, 2-ethoxycarbonylphenyl acrylate, 2- chlorophenyl acrylate, p-tolyl acrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, t-butyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, 2-hydroxyethyl methacrylate, 2- hydroxypropyl methacrylate,
- Examples of (meth)acrylic acid ester monomers useful in preparing oligomer (B) include ethyl acrylate, n-butyl acrylate, i-butyl acrylate, 2- ethylhexyl acrylate, n-octyl acrylate, n-decyl acrylate, n-heptyl acrylate, n-hexyl acrylate, phenoxyethyl acrylate, propyl acrylate, i-octyl acrylate, isoamyl acrylate, butoxyethyl acrylate, methoxyethlene glycol acrylate, 2-methoxyethyl acrylate, 3-methoxypropyl acrylate, 3-methoxybutyl acrylate, 2-ethoxymethyl acrylate, 3-ethoxypropyl acrylate, isodecyl acrylate, lauryl methacrylate, n-octyl
- ethyl acrylate is preferable, because it is easily available and favorable for the F value to be within the aforesaid range.
- the molecular weight of oligomer (B) is preferably within the range between 1000 and 20000. When this molecular weight is too low, the tack of the film of the present invention become too high. When this molecular weight is too high, the viscosity of the oligomer becomes so high that its handling becomes difficult.
- the reactive functional group useful in the invention include a (meth)acryloyl group, an allyl group, a vinyl group, an epoxy group, and an hydroxyl group.
- the number of these is at least 1 based on 10 or more, preferably 50 or more of the acrylic acid ester units in the oligomer, and preferably 1 based on 1000 or less, preferably 200 or less of the acrylic acid ester units of the oligomer.
- the number of this functional groups is too small, the copolymer of the aforesaid monomer and oligomer becomes paste-like, and does not form a film.
- the number of the functional group is too many, self-adhesiveness is lost.
- the Tg value of the homopolymer derived from monomer (A) is preferably 20 °C or higher.
- the Tg value of this homopolymer is lower than 20°C, the requirement cannot be satisfied that the self-adhesive film of the present invention has no or little tackiness.
- the Tg value of oligomer (B) is preferably lower than -20 °C.
- the adhesiveness of the self-adhesive film of the present invention becomes insufficient and it becomes impossible to impart flexibility to this film.
- the obtained film has no self-adhesiveness.
- the copolymer film of the invention may be prepared by exposing a mixture of monomer (A) and oligomer (B) to active energy radiation such as ultraviolet light or electron beam radiation so as to polymerize and harden the mixture.
- active energy radiation such as ultraviolet light or electron beam radiation
- photopolymerization initiators include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin-n-propyl ether, benzoin-n- butyl ether, benzyl, benzophenone, p-methylbenzophenone, diacetyl, eosin, thionine, Michler's ketone, acetophenone, 2-chlorothioxanthone, anthraquinone, chloroanthraquinone, 2-methylanthraquinone, ⁇ -hydroxyisobutylphenone, p-isopropyl- ⁇ -hydroxyisobutylphenone, o-, ⁇ -'-dichloro-4-phenoxyacetonhenone, 1-hydroxy-l-cyclohexylacetophenone, 2,2-
- the photopolymerization initiator is used preferably in a proportional amount normally ranging from about 0.1 to about 5 parts by weight based on 100 parts by weight of the sum amount of monomer (A) and oligomer (B).
- a photopolymerization promotor can be combined with the initiator.
- the photopolymerization promotor include tertiary amines such as triethylamine, triethanolamine, and 2- dimethylaminoethanol; alkylphosphines such as triphenylphosphine; thiols such as 3-thioglycol; and the like.
- the ultraviolet light may be provided by, for example, a mercury lamp, a high pressure mercury lamp, a ultra high pressure mercury lamp, a xenon lamp, a carbon arc, a metal halide lamp, sunlight, etc.
- the atmosphere in which the mixture is irradiated is preferably air or inert gas. When the atmosphere is air, it is preferable to use a high pressure mercury lamp as an irradiation source.
- the irradiation intensity of ultraviolet rays is preferably within the range between 0.1 and 100 mW, and the dose thereof is preferably within the range between 100 and 20,000 mJ/cm 2 .
- Polymerization by exposure to electron beam irradiation may be accomplished by employing a Cockcroft type accelerator, Cockcroft- Walton type one, resonant transformer type one, transformer type one, insulating core transformer type one, dynamitron type one, linear filament type one, broad beam type one, area beam type one, cathode electron type one, high frequency type one, and the like.
- the accelerating voltage for the electron beam irradiation is preferably within the range between 100 and 500 kN, and the dose thereof is preferably within the range between 10 and 1000 kGy.
- the aforesaid F value is within the range between 2.8 x 10 "3 and 3.7 x 10 "3 .
- the F value is less than 2.8 x 10 "3 , the adhesiveness is insufficient and this case is not preferable.
- this value is larger than 3.7 x 10 "3 , the present self-adhesive film has tackiness, and therefore, this case is also not preferable.
- the criterion as to whether or not there is tackiness referred to in the present invention is defined by finger tackiness.
- the films of the invention exhibit substantially no finger tackiness.
- the thickness of the film of the present invention is preferably within the range between 20 and 5000 ⁇ .
- the film When the film is too thin, the self- adhesiveness become lowered. On the contrary, when the film is too thick, the film becomes difficult to cure.
- This film may have smooth surfaces. Alternatively, it may employ uneven surfaces. When the film has such uneven surfaces it is preferred that they mate with each other.
- the height of the unevennesses is preferably within the range between 10 and 1000 ⁇ m. When the height is less than 10 ⁇ m, the adhesion strength is only minimally improved, and when the height exceeds 1000 ⁇ m, it becomes difficult for parts of the film to be fitted to each other.
- the self-adhesive film may be adhered to a substrate so as to be laminated.
- the utility value of the film is increased.
- the film adhered to many different substrates include plates, tapes or other molded products having any shape.
- the substrate may be made from plastic, glass, metal, and the like.
- 1-octanethiol were subjected to reflux in 1 L of methyl ethyl ketone in a nitrogen gas flow (about 80°C).
- a solution obtained by dissolving 0.8 g of azobisisobutylonitrile in methyl ethyl ketone was added dropwise to the reaction system, whereafter reflux under stirring was continued for 6 hours, so as to effect polymerization. Stopping the heating and the introduction of nitrogen, the obtained polymer was cooled to room temperature, whereafter 4.8 g of pyridine were added and stirred.
- a solution obtained by dissolving 5.4 g of acrylic acid chloride in methyl ethyl ketone was then added dropwise to the mixture, and stirred for 3 hours.
- the sandwiched mixture was cured by UV irradiation (UVL- ⁇ high pressure mercury lamp produced by Ushio Co., Ltd.; integral intensity: 900 mJ/cm 2 , measured by "UV-350” produced by ORC Inc.), so that a polymer film was prepared.
- UV irradiation UVL- ⁇ high pressure mercury lamp produced by Ushio Co., Ltd.; integral intensity: 900 mJ/cm 2 , measured by "UV-350” produced by ORC Inc.
- Fig. 1 shows a test specimen which comprises handle 1 secured acrylic plate 2.
- a layer of cyanoacrylate adhesive 3 secures a section of the self-adhesive film 4 to the plate 2.
- a PET film 5 covers the self- adhesive film 4.
- a second test identical specimen (now shown) is used to measure the 0 degree peel strength.
- the PET film 5 is removed from each of the test specimens.
- the self-adhesive films 4 were then mutually contacted to each other.
- a load of 500 g was applied to each of the test specimens for one minute after which these films were pulled in the direction perpendicular to the plane of the contacted surfaces by gripping the handles in the jaws of a "Tensilon 100". The force applied between these surfaces when they were debonded was reported as the 0 degree peel strength.
- the 0 degree peel strength was found to be 8.7 kgf/cm 2 (average value of 5 measured results).
- Example 2 The same experiment as in Example 1 was conducted with the exception that various acrylic acid ester monomers were used as reactive diluents.
- the Tg values of a homopolymer derived from the monomers used as the reactive diluent, F values, whether or not there was tackiness, and 0 degree peeling strength (kgf/cm 2 ) in these cases are set forth in Table 1.
- whether or not there was tackiness, and the degree of tackiness were judged according to whether or not there was sticky feeling and the degree of stickiness when a naked self-adhesive film was touched with a hand.
- EHA 2-ethylhexyl acrylate
- EA ethyl acrylate
- DCPA dicyclopentanyl acrylate
- Example 2 The same experiments as in Example 1 were conducted, with the exception that the ethyl acrylate oligomer synthesized in Example 1(1) was used as an oligomer, DCPA as a reactive diluent, so as to vary the composition ratio.
- the composition was applied between two 50 ⁇ m thick PET films and exposed to UV irradiation.
- whether or not there was tackiness was judged according to whether a naked self-adhesive film was sticky or not when it was touched with a hand. The results are set forth in Table 2.
- Table 2 Table 2
- Example 26 when the thickness of the self-adhesive film was varied is set forth in Fig. 3 (film thickness: 25 ⁇ m (Example 21), 50 ⁇ m (Example 22), 100 ⁇ m (Example 23), 200 ⁇ m (Example 24), and 300 ⁇ m (Example 25)).
- the composition used the ethyl acrylate oligomer synthesized in Example l(l)as an oligomer, and IBA as a reactive diluent. It can be seen from Fig. 3 that before the film thickness reaches to about 200 ⁇ m, the self-adhesion strength of the film increases as the film thickness is increased, and even if the film thickness is increased above this value, the self-adhesion strength is hardly changed.
- Example 26 Example 26
- a mixture of 50 parts of the ethyl acrylate oligomer synthesized in Example 1 (1) and 50 parts of isobornyl acrylate was sandwiched between two parts of a PET film with a thickness of 100 ⁇ m, and the whole film thickness was controlled by use of a knife coater, so as to become 300 ⁇ m, following which the sandwiched mixture was cured by electron beam irradiation (EB accelerator: an area beam type electron beam irradiator produced by Nisshin High Voltage Co., Ltd.; in a nitrogen atmosphere, at an accelerating voltage of 300 kV, at an electron current of 30 mA, and at a dose of 100 kGy), whereby a film was prepared.
- EB accelerator an area beam type electron beam irradiator produced by Nisshin High Voltage Co., Ltd.; in a nitrogen atmosphere, at an accelerating voltage of 300 kV, at an electron current of 30 mA, and at a dose of 100 kGy
- EB accelerator
- Example 27 A test sample with a handle was prepared as described in Example 1.
- Example 1 shows that the self-adhesive film of the present invention is hard to be influenced by dust and the like.
- Example 1 Test samples, each with a handle, were prepared as described in Example 1.
- the self-adhesive film surfaces were then adhered to each other according to the method in Example 1, and were then once debonded. These film surfaces were then again adhered in the same way as above, and 0 degree peel strength of the sample was determined and found to be 8.6 kgf/cm 2 . This value is almost equal to the result obtained in Example 1 , which shows that the self-adhesive film of the present invention can repeatedly used.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Laminated Bodies (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5217477A JPH0782388A (ja) | 1993-09-01 | 1993-09-01 | 自己接着性フィルム及びそれを用いた積層体 |
JP217477/93 | 1993-09-01 | ||
PCT/US1994/008166 WO1995006692A1 (en) | 1993-09-01 | 1994-07-20 | Self-adhesive film and laminate using the same |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0716673A1 true EP0716673A1 (en) | 1996-06-19 |
Family
ID=16704852
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94924476A Ceased EP0716673A1 (en) | 1993-09-01 | 1994-07-20 | Self-adhesive film and laminate using the same |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0716673A1 (ko) |
JP (1) | JPH0782388A (ko) |
KR (1) | KR960703999A (ko) |
CA (1) | CA2168972A1 (ko) |
WO (1) | WO1995006692A1 (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6972141B1 (en) | 1997-12-12 | 2005-12-06 | 3M Innovative Properties Company | Removable adhesive tape laminate and separable fastener |
US6531021B1 (en) | 1999-03-19 | 2003-03-11 | 3M Innovative Properties Company | Image graphic adhesive system using a non-tacky adhesive |
US6870670B2 (en) | 2001-04-06 | 2005-03-22 | 3M Innovative Properties Company | Screens and methods for displaying information |
KR20150095746A (ko) * | 2012-12-10 | 2015-08-21 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 액체 광학 접착제 조성물 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04216886A (ja) * | 1990-12-17 | 1992-08-06 | Lintec Corp | 耐ブリスター性粘着シート |
-
1993
- 1993-09-01 JP JP5217477A patent/JPH0782388A/ja active Pending
-
1994
- 1994-07-20 KR KR1019960700970A patent/KR960703999A/ko not_active Withdrawn
- 1994-07-20 EP EP94924476A patent/EP0716673A1/en not_active Ceased
- 1994-07-20 WO PCT/US1994/008166 patent/WO1995006692A1/en not_active Application Discontinuation
- 1994-07-20 CA CA002168972A patent/CA2168972A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO9506692A1 * |
Also Published As
Publication number | Publication date |
---|---|
JPH0782388A (ja) | 1995-03-28 |
WO1995006692A1 (en) | 1995-03-09 |
CA2168972A1 (en) | 1995-03-09 |
KR960703999A (ko) | 1996-08-31 |
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