WO2016027602A1 - 活性エネルギー線硬化性組成物 - Google Patents
活性エネルギー線硬化性組成物 Download PDFInfo
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- WO2016027602A1 WO2016027602A1 PCT/JP2015/070563 JP2015070563W WO2016027602A1 WO 2016027602 A1 WO2016027602 A1 WO 2016027602A1 JP 2015070563 W JP2015070563 W JP 2015070563W WO 2016027602 A1 WO2016027602 A1 WO 2016027602A1
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- Prior art keywords
- meth
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- acrylic
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012772 electrical insulation material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- URMHJZVLKKDTOJ-UHFFFAOYSA-N lithium;(3-methyl-1-phenylpentyl)benzene Chemical compound [Li+].C=1C=CC=CC=1[C-](CC(C)CC)C1=CC=CC=C1 URMHJZVLKKDTOJ-UHFFFAOYSA-N 0.000 description 1
- QGOZVRUBHUDZFY-UHFFFAOYSA-N lithium;1-(2-methoxyethoxy)ethanolate Chemical compound [Li+].COCCOC(C)[O-] QGOZVRUBHUDZFY-UHFFFAOYSA-N 0.000 description 1
- UUQLCJCZFWUWHH-UHFFFAOYSA-N lithium;1-phenylhexylbenzene Chemical compound [Li+].C=1C=CC=CC=1[C-](CCCCC)C1=CC=CC=C1 UUQLCJCZFWUWHH-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000011104 metalized film Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 1
- DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- HVYCQBKSRWZZGX-UHFFFAOYSA-N naphthalen-1-yl 2-methylprop-2-enoate Chemical compound C1=CC=C2C(OC(=O)C(=C)C)=CC=CC2=C1 HVYCQBKSRWZZGX-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000010734 process oil Chemical class 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003498 tellurium compounds Chemical class 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 150000003609 titanium compounds Chemical class 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
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PJPPDDJSRORGJA-UHFFFAOYSA-K tris(2,6-ditert-butyl-4-methylphenoxy)alumane Chemical compound [Al+3].CC1=CC(C(C)(C)C)=C([O-])C(C(C)(C)C)=C1.CC1=CC(C(C)(C)C)=C([O-])C(C(C)(C)C)=C1.CC1=CC(C(C)(C)C)=C([O-])C(C(C)(C)C)=C1 PJPPDDJSRORGJA-UHFFFAOYSA-K 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/026—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising acrylic acid, methacrylic acid or derivatives thereof
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Definitions
- the present invention relates to a polymer composition having active energy ray curability. Specifically, the present invention relates to an active energy ray-curable composition that has a high curing rate upon irradiation with active energy rays, is not deformed, and the obtained cured product is excellent in transparency and flexibility.
- Active energy ray-curable compositions that are cured by irradiation with active energy rays such as ultraviolet rays and electron beams are known, and are used for applications such as adhesives, adhesives, paints, inks, coating materials, and optical modeling materials. It has been.
- a (meth) acrylic block copolymer consisting of a methacrylic polymer block and an acrylic polymer block is excellent in tackiness, moldability, weather resistance, etc., making use of these characteristics, adhesives, adhesives, coatings Expansion to applications such as materials and various molding materials is expected.
- an active energy ray-curable composition comprising a (meth) acrylic block copolymer having an active energy ray-curable functional group, comprising a methacrylic polymer block and an acrylic polymer block
- a (meth) acrylic block copolymer having an active energy ray-curable functional group comprising a methacrylic polymer block and an acrylic polymer block
- the object of the present invention is that the curability by active energy rays is good, and when applied to a substrate such as an adhesive or a coating material and then cured by active energy rays, the viscosity is low and the coatability is excellent. It is to provide an active energy ray-curable composition that is excellent in flexibility of a cured product.
- the object is [1] A (meth) acrylic polymer block (aA) having an active energy ray-curable group containing a partial structure represented by the following general formula (1) (hereinafter referred to as “partial structure (1)”) and active energy
- An active energy ray-curable composition in the range of 2 to 2.0; [2] The active energy ray-curable composition according to [1], further comprising a photopolymerization initiator; and [3] (meth) acrylic triblock copolymers (A) and (meth) acrylic [1] or [1], wherein the active energy ray-curable group of the diblock copolymer (B) includes a partial structure represented by the following general formula (2) (hereinafter referred to as “partial structure (2)”) [2] active energy ray-curable composition; Is achieved by providing
- R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms
- R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms
- R 2 and R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms
- X represents O, S, Or N (R 6 )
- R 6 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms
- n represents an integer of 1 to 20
- the active energy ray-curable composition of the present invention is cured with active energy rays, and applied with a low viscosity when used after being applied to a substrate such as an adhesive or a coating material and then cured with active energy rays.
- a cured product having excellent properties and excellent flexibility after curing can be obtained.
- the active energy ray-curable composition of the present invention contains a (meth) acrylic triblock copolymer (A).
- (meth) acryl means a generic name of “methacryl” and “acryl”
- (meth) acryloyl” described later means a generic name of “methacryloyl” and “acryloyl”.
- (Meth) acrylate”, which will be described later, is a generic term for “methacrylate” and “acrylate”.
- the (meth) acrylic triblock copolymer (A) contains a (meth) acrylic polymer block (aA) having an active energy ray-curable group containing the partial structure (1).
- an active energy ray means a light beam, electromagnetic waves, particle beams, and a combination thereof.
- light rays include far ultraviolet rays, ultraviolet rays (UV), near ultraviolet rays, visible rays, and infrared rays
- electromagnetic waves include X-rays and ⁇ rays
- particle beams include electron beams (EB) and proton rays ( ⁇ Line) and neutron beam.
- ultraviolet rays and electron beams are preferable, and ultraviolet rays are more preferable, from the viewpoint of curing speed, availability of an irradiation apparatus, price, and the like.
- Partial structure (1) is represented by the following general formula (1).
- examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec- Butyl, t-butyl, 2-methylbutyl, 3-methylbutyl, 2-ethylbutyl, 3-ethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, n-pentyl, neopentyl Group, n-hexyl group, 2-methylpentyl group, 3-methylpentyl group, n-decyl and other alkyl groups; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and other cycloalkyl groups
- the active energy ray-curable composition of the present invention is applied to a substrate as an adhesive, a coating agent or the like, cured with active energy rays and used as a cured product, and then it becomes necessary to discard the cured product. There is a case. At that time, it is desirable that such a cured product can be easily peeled from the substrate, for example, by a wet heat decomposition method.
- the active energy ray-curable group containing the partial structure (2) is preferable among the active energy ray-curable groups containing the partial structure (1) from the viewpoint of excellent wet heat decomposability after curing.
- Partial structure (2) is represented by the following general formula (2).
- R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms
- R 2 and R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms
- X represents O, S, Or N (R 6 )
- R 6 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms
- n represents an integer of 1 to 20
- Specific examples and preferred examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R 1 in general formula (2) include the same hydrocarbon groups as R 1 in general formula (1).
- examples of the hydrocarbon group having 1 to 6 carbon atoms independently represented by R 2 and R 3 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group.
- a methyl group and an ethyl group are preferable, and a methyl group is most preferable.
- X represents O, S or N (R 6 ) (R 6 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms).
- R 6 represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms.
- examples of the hydrocarbon group having 1 to 6 carbon atoms represented by R 6 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, 3-methylbutyl group, 2-ethylbutyl group, 3-ethylbutyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group, n-pentyl group And alkyl groups such as neopentyl group, n-hexyl group, 2-methylpentyl group and 3-methylpentyl group; cycloal
- the integer of 1 to 20 represented by n is preferably 2 to 5 from the viewpoint of fluidity and curing speed of the active energy ray-curable composition.
- the content of the partial structure (1) in the (meth) acrylic polymer block (aA) is 0.2 to 100 mol based on all monomer units forming the (meth) acrylic polymer block (aA). %, Preferably 10 to 90 mol%, more preferably 25 to 80 mol%.
- the (meth) acrylic polymer block (aA) includes a monomer unit formed by polymerizing a monomer containing a (meth) acrylic acid ester.
- a (meth) acrylic acid ester a monofunctional (meth) acrylic acid ester having one (meth) acryloyl group and a polyfunctional (meth) acrylic acid ester having two or more (meth) acryloyl groups are used. can do.
- Examples of the monofunctional (meth) acrylic acid ester that can form the (meth) acrylic polymer block (aA) include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, (meth) Isopropyl acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isobornyl (meth) acrylate, (meth) acrylic acid Dodecyl, 2-methoxyethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, trimethoxysilylpropyl (meth) acrylate, 2-amino (meth) acrylate Ethyl, (meth) acrylic acid N, N-
- alkyl methacrylates having an alkyl group having 5 or less carbon atoms such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, t-butyl methacrylate, Most preferred is methyl methacrylate.
- (Meth) acryloyloxy group represented by C (O) O ” is selectively polymerized to have a methacryl having an active energy ray-curable group containing a partial structure (2) in which R 1 is R 4 and X is O It is preferable because a polymer block (aA) is obtained.
- R 2 and R 3 each independently represents a hydrocarbon group having 1 to 6 carbon atoms
- R 4 and R 5 each independently represents a hydrogen atom or a methyl group
- n represents 1 to 20
- examples of the hydrocarbon group having 1 to 6 carbon atoms that can be R 2 and R 3 include the same groups as R 2 and R 3 in the general formula (2).
- n is preferably 2 to 5 from the viewpoints of fluidity and curing speed of the active energy ray-curable composition.
- R 4 is preferably a methyl group from the viewpoint of increasing the selectivity of polymerization. From the viewpoint of easy availability of di (meth) acrylate (3), R 4 and R 5 are preferably the same. From the above viewpoints, it is most preferable that R 4 and R 5 are both methyl groups.
- Examples of the di (meth) acrylate (3) include 1,1-dimethylpropane-1,3-diol di (meth) acrylate, 1,1-dimethylbutane-1,4-diol di (meth) acrylate, 1,1 -Dimethylpentane-1,5-diol di (meth) acrylate, 1,1-dimethylhexane-1,6-diol di (meth) acrylate, 1,1-diethylpropane-1,3-diol di (meth) acrylate, 1, 1-diethylbutane-1,4-diol di (meth) acrylate, 1,1-diethylpentane-1,5-diol di (meth) acrylate, 1,1-diethylhexane-1,6-diol di (meth) acrylate, etc.
- acrylic acid esters may be used alone or in combination of two or more.
- the content of the monomer unit formed from the (meth) acrylic acid ester in the (meth) acrylic polymer block (aA) is the total monomer forming the (meth) acrylic polymer block (aA).
- the range is preferably 90 to 100 mol%, more preferably 95 to 100 mol%, and may be 100 mol% with respect to the unit.
- the (meth) acrylic polymer block (aA) contains a monomer unit formed from di (meth) acrylate (3), a single unit formed from di (meth) acrylate (3) is used.
- the content of the monomer unit is preferably in the range of 0.2 to 100 mol%, preferably in the range of 10 to 90 mol%, based on all the monomer units forming the (meth) acrylic polymer block (aA). Is more preferable, and the range of 25 to 80 mol% is more preferable. Furthermore, the total content of the monomer unit formed from methyl methacrylate and the monomer unit formed from di (meth) acrylate (3) is the (meth) acrylic polymer block (aA). The range of 80 to 100 mol% is preferable, the range of 90 to 100 mol% is more preferable, the range of 95 to 100 mol% is more preferable, and the range is 100 mol% with respect to the total monomer units to be formed. Good.
- the (meth) acrylic polymer block (aA) may have a monomer unit formed from a monomer other than the (meth) acrylic acid ester.
- the other monomer include ⁇ -alkoxy acrylate esters such as methyl ⁇ -methoxyacrylate and methyl ⁇ -ethoxyacrylate; crotonic acid esters such as methyl crotonate and ethyl crotonate; 3-alkoxyacrylic acid esters such as acid esters; acrylamides such as N-isopropylacrylamide, Nt-butylacrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide; N-isopropylmethacrylamide, Nt- Methacrylamide such as butylmethacrylamide, N, N-dimethylmethacrylamide, N, N-diethylmethacrylamide; methyl 2-phenylacrylate, ethyl 2-phenylacrylate, n-butyl 2-bromo
- the content of the monomer unit formed from the other monomer in the (meth) acrylic polymer block (aA) is the total monomer forming the (meth) acrylic polymer block (aA).
- the amount is preferably 10 mol% or less, more preferably 5 mol% or less, based on the unit.
- Mn (Mn (aA)) per (meth) acrylic polymer block (aA) is not particularly limited, but from the viewpoints of handleability, fluidity, mechanical properties and the like of the obtained active energy ray-curable composition.
- the range of 500 to 1,000,000 is preferred, and the range of 1,000 to 300,000 is more preferred.
- Mn means the number average molecular weight of standard polystyrene conversion measured by the gel permeation chromatography (GPC) method.
- two (meth) acrylic polymer blocks (aA) may be included in the (meth) acrylic triblock copolymer (A).
- the polymer block properties such as the composition of may be the same or different.
- (Meth) acrylic triblock copolymer (A) contains (meth) acrylic polymer block (bA) having no active energy ray-curable group.
- the active energy ray-curable group means a functional group that exhibits polymerizability upon irradiation with the active energy ray.
- the active energy ray-curable group include ethylenic double bonds such as (meth) acryloyl group, (meth) acryloyloxy group, vinyl group, allyl group, vinyl ether group, 1,3-dienyl group, and styryl group ( In particular, a functional group having a general formula CH 2 ⁇ CHR— (wherein R is an alkyl group or a hydrogen atom)); an epoxy group, an oxetanyl group, a thiol group, a maleimide group, and the like.
- the (meth) acrylic polymer block (bA) is composed of monomer units formed by polymerizing a monomer containing a (meth) acrylic acid ester and has the above-described active energy ray-curable group. It is a polymer block that does not.
- Examples of such (meth) acrylic acid esters include methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, t-butyl acrylate, cyclohexyl acrylate, and 2-ethylhexyl acrylate.
- (meth) acrylic acid esters monofunctional alkyl acrylates having an alkyl group having 4 or more carbon atoms, such as n-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, and the like; and Monofunctional alkyl methacrylates having an alkyl group having 6 or more carbon atoms such as 2-ethylhexyl methacrylate and dodecyl methacrylate are preferred.
- These (meth) acrylic acid esters may be used alone or in combination of two or more.
- the content of the monomer unit formed by the (meth) acrylic acid ester in the (meth) acrylic polymer block (bA) is the total amount of the monomer unit forming the (meth) acrylic polymer block (bA).
- the amount is preferably 90 mol% or more, more preferably 95 mol% or more, based on the body unit.
- the (meth) acrylic polymer block (bA) may have a monomer unit formed from a monomer other than the (meth) acrylic acid ester.
- the other monomer include ⁇ -alkoxy acrylate esters such as methyl ⁇ -methoxyacrylate and methyl ⁇ -ethoxyacrylate; crotonic acid esters such as methyl crotonate and ethyl crotonate; 3-alkoxyacrylic acid esters such as acid esters; acrylamides such as N-isopropylacrylamide, Nt-butylacrylamide, N, N-dimethylacrylamide, N, N-diethylacrylamide; N-isopropylmethacrylamide, Nt- Methacrylamide such as butylmethacrylamide, N, N-dimethylmethacrylamide, N, N-diethylmethacrylamide; methyl 2-phenylacrylate, ethyl 2-phenylacrylate, n-butyl 2-bromo
- the content of the monomer unit formed by the other monomer in the (meth) acrylic polymer block (bA) is the total monomer forming the (meth) acrylic polymer block (bA).
- the amount is preferably 10 mol% or less, more preferably 5 mol% or less, based on the unit.
- Mn (Mn (bA)) per (meth) acrylic polymer block (bA) is not particularly limited, but the handleability, fluidity of the resulting (meth) acrylic triblock copolymer (A), From the viewpoint of mechanical properties and the like, the range of 3,000 to 2,000,000 is preferable, and the range of 5,000 to 1,000,000 is more preferable.
- Two (meth) acrylic polymer blocks (bA) may be included in the (meth) acrylic triblock copolymer (A), but in that case, the molecular weight, monomer unit, The polymer block properties such as the composition of may be the same or different.
- the (meth) acrylic triblock copolymer (A) has at least one (meth) acrylic polymer block (aA) and at least one (meth) acrylic polymer block (bA). From the viewpoints of the curing speed of the (meth) acrylic triblock copolymer (A), ease of production, etc., it is a block copolymer at both ends of one (meth) acrylic polymer block (bA) ( A triblock copolymer in which each one of the (meth) acrylic polymer block (aA) is bonded is preferable.
- Ratio of total mass of (meth) acrylic polymer block (aA) and total mass of (meth) acrylic polymer block (bA) constituting (meth) acrylic triblock copolymer (A) (( The meth) acrylic polymer block (aA) :( meth) acrylic polymer block (bA)) is not particularly limited, but is preferably 90:10 to 5:95.
- proportion of the (meth) acrylic polymer block (aA) in the (meth) acrylic triblock copolymer (A) is 5% by mass or more, the active energy ray curability becomes good and 90% by mass or less. Is preferable because viscoelasticity is improved.
- the Mn (Mn (A)) of the (meth) acrylic triblock copolymer (A) is not particularly limited, but from the viewpoints of handleability, fluidity, mechanical properties and the like of the active energy ray-curable composition of the present invention.
- the range of 4,000 to 4,000,000 is preferable, and the range of 7,000 to 2,000,000 is more preferable.
- the molecular weight distribution of the (meth) acrylic triblock copolymer (A), that is, the weight average molecular weight / number average molecular weight (Mw / Mn) is preferably in the range of 1.02 to 2.00, and 1.05 to 1.80. Is more preferable, and a range of 1.10 to 1.50 is more preferable.
- Mw means the weight average molecular weight of standard polystyrene conversion measured by the gel permeation chromatography (GPC) method.
- the content of the partial structure (1) in the (meth) acrylic triblock copolymer (A) is 0 with respect to all monomer units forming the (meth) acrylic triblock copolymer (A).
- the range is preferably from 1 to 20 mol%, more preferably from 2 to 15 mol%, still more preferably from 3 to 10 mol%.
- the number of partial structures (1) contained in the (meth) acrylic triblock copolymer (A) is preferably 4 or more, and 8 or more per polymer molecule. More preferably.
- the active energy ray-curable group containing the partial structure (1) of the (meth) acrylic polymer block (aA) is a (meth) acrylic triblock copolymer (A).
- a side chain of the (meth) acrylic polymer block (aA) but at least a (meth) acrylic polymer from the viewpoint of introducing a preferred number of partial structures (1). It is preferable that it exists in the side chain of a block (aA).
- the active energy ray-curable composition of the present invention contains a (meth) acrylic diblock copolymer (B).
- the (meth) acrylic diblock copolymer (B) contains a (meth) acrylic polymer block (aB) having an active energy ray-curable group containing the partial structure (1).
- R 1 in the formula (1) are the same as those in the case of the (meth) acrylic polymer block (aA).
- the active energy ray-curable group containing the partial structure (2) is preferable among the active energy ray-curable groups containing the partial structure (1) from the viewpoint of excellent wet heat decomposability after curing.
- Specific examples and preferred examples of R 2 and R 3 in the general formula (2) representing the partial structure (2), and those having 1 to 20 carbon atoms represented by R 1 in the general formula (2) representing the partial structure (2) Specific examples and preferred examples of hydrocarbon groups, specific examples of a hydrocarbon group having 1 to 6 carbon atoms represented by R 6 when X is N (R 6 ), preferred examples of X, and preferred examples of n are: The same as in the case of the (meth) acrylic polymer block (aA).
- the content of the partial structure (1) in the (meth) acrylic polymer block (aB) is 0.2 to 100 mol based on all monomer units forming the (meth) acrylic polymer block (aB). %, Preferably 10 to 90 mol%, more preferably 25 to 80 mol%.
- the (meth) acrylic polymer block (aB) includes a monomer unit formed by polymerizing a monomer containing a (meth) acrylic acid ester.
- a (meth) acrylic acid ester a monofunctional (meth) acrylic acid ester having one (meth) acryloyl group and a polyfunctional (meth) acrylic acid ester having two or more (meth) acryloyl groups are used. can do.
- Specific examples and preferred examples of the monofunctional (meth) acrylic acid ester and polyfunctional (meth) acrylic acid ester are the same as those in the case of the (meth) acrylic polymer block (aA). These (meth) acrylic acid esters may be used alone or in combination of two or more.
- the content of the monomer unit formed from the (meth) acrylic acid ester in the (meth) acrylic polymer block (aB) is the total monomer forming the (meth) acrylic polymer block (aB).
- the range is preferably 90 to 100 mol%, more preferably 95 to 100 mol%, and may be 100 mol% with respect to the unit.
- the (meth) acrylic polymer block (aB) contains a monomer unit formed from di (meth) acrylate (3), a single unit formed from di (meth) acrylate (3) is used.
- the content of the monomer unit is preferably in the range of 0.2 to 100 mol%, preferably in the range of 10 to 90 mol%, based on all the monomer units forming the (meth) acrylic polymer block (aA). Is more preferable, and the range of 25 to 80 mol% is more preferable. Furthermore, the total content of the monomer unit formed from methyl methacrylate and the monomer unit formed from di (meth) acrylate (3) is (meth) acrylic polymer block (aB). The range of 80 to 100 mol% is preferable, the range of 90 to 100 mol% is more preferable, the range of 95 to 100 mol% is more preferable, and the range is 100 mol% with respect to the total monomer units to be formed. Good.
- the (meth) acrylic polymer block (aB) may have a monomer unit formed from a monomer other than the (meth) acrylic acid ester. Specific examples and preferred examples of the other monomers are the same as in the case of the (meth) acrylic polymer block (aA). These other monomers may be used alone or in combination of two or more.
- the content of the monomer unit formed from the other monomer in the (meth) acrylic polymer block (aB) is the total monomer forming the (meth) acrylic polymer block (aB).
- the amount is preferably 10 mol% or less, more preferably 5 mol% or less, based on the unit.
- the Mn (Mn (aB)) of the (meth) acrylic polymer block (aB) is not particularly limited, but from the viewpoint of the handleability, fluidity, mechanical properties and the like of the obtained active energy ray-curable composition, 500 to The range of 1,000,000 is preferable, and the range of 1,000 to 300,000 is more preferable.
- the (meth) acrylic diblock copolymer (B) contains a (meth) acrylic polymer block (bB) having no active energy ray-curable group.
- the (meth) acrylic polymer block (bB) is composed of monomer units formed by polymerizing a monomer containing a (meth) acrylic acid ester, and has the above-described active energy ray-curable group. It is a polymer block that does not.
- the content of the monomer unit formed by the (meth) acrylic acid ester in the (meth) acrylic polymer block (bB) is the total amount of the monomer unit forming the (meth) acrylic polymer block (bB).
- the amount is preferably 90 mol% or more, more preferably 95 mol% or more, based on the body unit.
- the (meth) acrylic polymer block (bB) may have a monomer unit formed from a monomer other than the (meth) acrylic acid ester. Specific examples of the other monomers are the same as in the case of the (meth) acrylic polymer block (bA). These other monomers may be used alone or in combination of two or more.
- the content of the monomer unit formed by the other monomer in the (meth) acrylic polymer block (bB) is the total monomer forming the (meth) acrylic polymer block (bB).
- the amount is preferably 10 mol% or less, more preferably 5 mol% or less, based on the unit.
- the Mn (Mn (bB)) of the (meth) acrylic polymer block (bB) is not particularly limited, but the handleability, fluidity, mechanical properties, etc. of the resulting (meth) acrylic diblock copolymer (B) From these points, the range of 3,000 to 2,000,000 is preferable, and the range of 5,000 to 1,000,000 is more preferable.
- Ratio of mass of (meth) acrylic polymer block (aB) and mass of (meth) acrylic polymer block (bB) constituting (meth) acrylic diblock copolymer (B) ((meth)
- the acrylic polymer block (aB) :( meth) acrylic polymer block (bB)) is not particularly limited but is preferably 90:10 to 2:98.
- the proportion of the (meth) acrylic polymer block (aB) in the (meth) acrylic diblock copolymer (B) is 2% by mass or more, the active energy ray curability is good, and 90% by mass or less. Is preferable because viscoelasticity is improved.
- the Mn (Mn (B)) of the (meth) acrylic diblock copolymer (B) is not particularly limited, but is 3,500 to 3,000,000 from the viewpoints of handleability, fluidity, mechanical properties and the like. Is preferably within the range of 6,000 to 1,300,000.
- the molecular weight distribution (Mw / Mn) of the (meth) acrylic diblock copolymer (B) is preferably in the range of 1.02 to 2.00, more preferably in the range of 1.05 to 1.80, and 1.10. A range of ⁇ 1.50 is more preferable.
- the content of the partial structure (1) in the (meth) acrylic diblock copolymer (B) is 0 with respect to all monomer units forming the (meth) acrylic diblock copolymer (B).
- the range of 0.05 to 20 mol% is preferable, the range of 1 to 15 mol% is more preferable, and the range of 1.5 to 10 mol% is more preferable.
- the number of the partial structures (1) in the (meth) acrylic diblock copolymer (B) is preferably 2 or more per molecule of the polymer, more preferably 4 or more from the viewpoint of curing speed. preferable.
- the active energy ray-curable group containing the partial structure (1) of the (meth) acrylic polymer block (aB) is a (meth) acrylic diblock. Although it may be at the terminal of the copolymer (B) or in the side chain of the (meth) acrylic polymer block (aB), at least (from the viewpoint of introducing a preferred number of partial structures (1) It is preferable that it exists in the side chain of a (meth) acrylic-type polymer block (aB).
- the (meth) acrylic diblock polymer (B) has a structural unit similar to the (meth) acrylic triblock copolymer (A)
- the (meth) acrylic diblock polymer (B) is compared with a general reactive diluent (meth).
- An active energy ray-curable composition having high compatibility with the acrylic triblock copolymer (A) and excellent transparency and mechanical properties of the cured product can be obtained.
- the method for producing the (meth) acrylic triblock copolymer (A) and the (meth) acrylic diblock copolymer (B) in the present invention is not particularly limited, but an anionic polymerization method or a radical polymerization method is preferable. From the viewpoint of polymerization control, the living anion polymerization method or the living radical polymerization method is more preferable, and the living anion polymerization method is more preferable.
- Living radical polymerization methods include polymerization methods using chain transfer agents such as polysulfides, polymerization methods using cobalt porphyrin complexes, polymerization methods using nitroxides (see International Publication No. 2004/014926), and high-cycle heterogeneity such as organic tellurium compounds.
- Polymerization method using elemental compounds see Japanese Patent No. 3839829
- RAFT reversible addition / elimination chain transfer polymerization method
- ATRP atom transfer radical polymerization method
- Japanese Patent No. 3040172 International Publication No. 2004/013192
- an atom transfer radical polymerization method is preferred, and a metal complex having an organic halide or a sulfonyl halide compound as an initiator and at least one selected from Fe, Ru, Ni, and Cu as a central metal is used.
- An atom transfer radical polymerization method using a catalyst is more preferable.
- Living anionic polymerization methods include living polymerization using an organic rare earth metal complex as a polymerization initiator (see JP 06-93060 A), alkali metal or alkaline earth metal salts using an organic alkali metal compound as a polymerization initiator, and the like.
- a living anion polymerization in the presence of a mineral salt see Japanese Patent Publication No. 05-507737
- a living anion polymerization using an organic alkali metal compound as a polymerization initiator in the presence of an organoaluminum compound Japanese Patent Laid-open No. Hei 05 (1994)
- 11-335432 and International Publication No. 2013/141105 are examples of organic alkali metal compound as a polymerization initiator.
- living anionic polymerization using an organic alkali metal compound as a polymerization initiator in the presence of an organic aluminum compound is more preferred.
- organoaluminum compounds represented by the following general formula (A-1) or (A-2).
- AlR 7 (R 8 ) (R 9 ) (A-1) (Wherein R 7 represents a monovalent saturated hydrocarbon group, a monovalent aromatic hydrocarbon group, an alkoxy group, an aryloxy group or an N, N-disubstituted amino group, and R 8 and R 9 are each independently Or R 8 and R 9 are bonded to each other to form an aryleneoxy group)
- AlR 10 (R 11 ) (R 12 ) (A-2) wherein R 10 represents an aryloxy group, and R 11 and R 12 each independently represent a monovalent saturated hydrocarbon group, a monovalent aromatic hydrocarbon group, an alkoxy group, or an N, N-disubstituted amino group.
- examples of the aryloxy group independently represented by R 7 , R 8 , R 9 and R 10 include a phenoxy group, 2-methylphenoxy group, 4 -Methylphenoxy group, 2,6-dimethylphenoxy group, 2,4-di-t-butylphenoxy group, 2,6-di-t-butylphenoxy group, 2,6-di-t-butyl-4-methyl Phenoxy group, 2,6-di-t-butyl-4-ethylphenoxy group, 2,6-diphenylphenoxy group, 1-naphthoxy group, 2-naphthoxy group, 9-phenanthryloxy group, 1-pyrenyloxy group, Examples include 7-methoxy-2-naphthoxy group.
- examples of the aryleneoxy group formed by bonding R 8 and R 9 to each other include 2,2′-biphenol, 2,2′-methylenebisphenol, 2,2 ′, and the like.
- excluded the hydrogen atom of these two phenolic hydroxyl groups in the compound which has two phenolic hydroxyl groups, such as a naphthol, is mentioned.
- one or more hydrogen atoms contained in the above aryloxy group and aryleneoxy group may be substituted with a substituent.
- substituents include a methoxy group, an ethoxy group, an isopropoxy group, Examples thereof include alkoxy groups such as t-butoxy group; halogen atoms such as chlorine and bromine.
- the monovalent saturated hydrocarbon groups represented by R 7 , R 11 and R 12 are, for example, methyl group, ethyl group, n-propyl group.
- the monovalent aromatic hydrocarbon group includes, for example, an aryl group such as a phenyl group; the aralkyl group such as a benzyl group; and the alkoxy group includes, for example, a methoxy group and an ethoxy group. , Isopropoxy group, t-butoxy group and the like.
- the N, N-disubstituted amino group include a dimethylamino group, a diethylamino group, and a diisopropylamino group.
- Dialkylamino groups such as bis (trimethylsilyl) amino group and the like.
- One or more hydrogen atoms contained in the above-mentioned monovalent saturated hydrocarbon group, monovalent aromatic hydrocarbon group, alkoxy group and N, N-disubstituted amino group may be substituted with a substituent.
- substituents include alkoxy groups such as methoxy group, ethoxy group, isopropoxy group and t-butoxy group; halogen atoms such as chlorine and bromine.
- organoaluminum compound (A-1) examples include ethylbis (2,6-di-t-butyl-4-methylphenoxy) aluminum, ethylbis (2,6-di-t-butylphenoxy) aluminum, ethyl [2 , 2'-methylenebis (4-methyl-6-t-butylphenoxy)] aluminum, isobutylbis (2,6-di-t-butyl-4-methylphenoxy) aluminum, isobutylbis (2,6-di-t -Butylphenoxy) aluminum, isobutyl [2,2'-methylenebis (4-methyl-6-t-butylphenoxy)] aluminum, n-octylbis (2,6-di-t-butyl-4-methylphenoxy) aluminum, n-octylbis (2,6-di-t-butylphenoxy) aluminum, n-octyl [2,2′-methyle Bis (4-methyl-6-t-butyl)
- isobutyl bis (2,6-di-t-butyl-4-methylphenoxy) aluminum, isobutyl bis (2,6 -Di-t-butylphenoxy) aluminum, isobutyl [2,2'-methylenebis (4-methyl-6-t-butylphenoxy)] aluminum and the like are preferable.
- organoaluminum compound (A-2) examples include diethyl (2,6-di-t-butyl-4-methylphenoxy) aluminum, diethyl (2,6-di-t-butylphenoxy) aluminum, diisobutyl (2 , 6-Di-t-butyl-4-methylphenoxy) aluminum, diisobutyl (2,6-di-t-butylphenoxy) aluminum, di-n-octyl (2,6-di-t-butyl-4-methylphenoxy) ) Aluminum, di-n-octyl (2,6-di-t-butylphenoxy) aluminum, and the like. These organoaluminum compounds may be used alone or in combination of two or more.
- the Lewis base includes an ether bond and / or a tertiary amine structure in the molecule (—RN (R ′ —) — R ′′ —: R, R ′ and R ′′ represent a divalent organic group).
- R, R ′ and R ′′ represent a divalent organic group.
- the ether is a cyclic ether having two or more ether bonds in the molecule or an acyclic ether having one or more ether bonds in the molecule from the viewpoint of high polymerization initiation efficiency and living property of the polymerization terminal anion. Is preferred.
- Examples of the cyclic ether having two or more ether bonds in the molecule include crown ethers such as 12-crown-4, 15-crown-5, and 18-crown-6.
- acyclic ether having one or more ether bonds in the molecule examples include acyclic monoethers such as dimethyl ether, diethyl ether, diisopropyl ether, dibutyl ether, and anisole; 1,2-dimethoxyethane, 1,2-diethoxy Ethane, 1,2-diisopropoxyethane, 1,2-dibutoxyethane, 1,2-diphenoxyethane, 1,2-dimethoxypropane, 1,2-diethoxypropane, 1,2-diisopropoxypropane 1,2-dibutoxypropane, 1,2-diphenoxypropane, 1,3-dimethoxypropane, 1,3-diethoxypropane, 1,3-diisopropoxypropane, 1,3-dibutoxypropane, , 3-diphenoxypropane, 1,4-dimethoxybutane, 1,4-diethoxybutane, , 4-diisopropoxybutane, 1,4-di
- a tertiary polyamine As the compound having a tertiary amine structure in the molecule used as the Lewis base, a tertiary polyamine is exemplified.
- a tertiary polyamine means a compound having two or more tertiary amine structures in the molecule. Examples of the tertiary polyamine include N, N, N ′, N′-tetramethylethylenediamine, N, N, N ′, N′-tetraethylethylenediamine, N, N, N ′, N ′′, N ′′ -pentamethyl.
- Linear polyamines such as diethylenetriamine, 1,1,4,7,10,10-hexamethyltriethylenetetraamine, tris [2- (dimethylamino) ethyl] amine; 1,3,5-trimethylhexahydro-1, 3,5-triazine, 1,4,7-trimethyl-1,4,7-triazacyclononane, 1,4,7,10,13,16-hexamethyl-1,4,7,10,13,16 -Non-aromatic heterocyclic compounds such as hexaazacyclooctadecane; aromatic heterocyclic compounds such as 2,2'-bipyridyl, 2,2 ': 6', 2 "-terpyridine, and the like.
- a compound having one or more ether bonds and one or more tertiary amine structures in the molecule may be used as the Lewis base.
- An example of such a compound is tris [2- (2-methoxyethoxy) ethyl] amine.
- Lewis bases may be used alone or in combination of two or more.
- organolithium compound examples include t-butyllithium, 1,1-dimethylpropyllithium, 1,1-diphenylhexyllithium, 1,1-diphenyl-3-methylpentyllithium, ethyl ⁇ -lithioisobutyrate, butyl ⁇ -lithioisobutyrate, methyl ⁇ -lithioisobutyrate, isopropyl lithium, sec-butyl lithium, 1-methylbutyl lithium, 2-ethylpropyl lithium, 1-methylpentyl lithium, cyclohexyl lithium, diphenylmethyl lithium, ⁇ - Examples thereof include methylbenzyl lithium, methyl lithium, n-propyl lithium, n-butyl lithium, n-pentyl lithium and the like.
- An organolithium compound having 3 to 40 carbon atoms and having a chemical structure having a secondary carbon atom as an anion center is preferred, and sec-butyllithium is particularly preferred.
- These organolithium compounds may be used alone or in combination of two or more.
- the living anionic polymerization is preferably carried out in the presence of an organic solvent from the viewpoint of controlling the temperature of the anionic polymerization and making the system uniform so that the anionic polymerization proceeds smoothly.
- Organic solvents include hydrocarbons such as toluene, xylene, cyclohexane, and methylcyclohexane from the viewpoints of safety, separability from water in washing the reaction mixture after anionic polymerization, and ease of recovery and reuse; chloroform Halogenated hydrocarbons such as methylene chloride and carbon tetrachloride; esters such as dimethyl phthalate are preferred.
- These organic solvents may be used alone or in combination of two or more.
- additives may be present in the anionic polymerization reaction system, if necessary.
- the other additives include inorganic salts such as lithium chloride; metal alkoxides such as lithium methoxyethoxy ethoxide and potassium t-butoxide; tetraethylammonium chloride and tetraethylphosphonium bromide.
- the living anionic polymerization is preferably performed at ⁇ 30 to 25 ° C.
- the temperature is lower than ⁇ 30 ° C., the polymerization rate decreases and the productivity tends to decrease.
- the temperature is higher than 25 ° C., it tends to be difficult to polymerize the (meth) acrylic polymer block (a) including the partial structure (1) with good living property.
- the living anionic polymerization is preferably performed in an atmosphere of an inert gas such as nitrogen, argon or helium. Moreover, it is preferable to carry out it under sufficient stirring conditions so that a polymerization reaction system may become uniform.
- an inert gas such as nitrogen, argon or helium.
- the Lewis base is brought into contact with the organoaluminum compound before contacting with the organolithium compound. It is preferable to add.
- the organoaluminum compound may be added to the reaction system before the monomer or simultaneously. When the organoaluminum compound is added to the reaction system simultaneously with the monomer, the organoaluminum compound may be added after separately mixing with the monomer.
- a polymer block containing a precursor structure can be obtained by polymerizing a monomer containing a polymerizable functional group and a compound containing a precursor structure.
- the polymerizable functional group include a styryl group, a 1,3-dienyl group, a vinyloxy group, and a (meth) acryloyl group, and a (meth) acryloyl group is preferable.
- Precursor structures include hydroxyl groups protected by hydroxyl groups and protecting groups (silyloxy groups, acyloxy groups, alkoxy groups, etc.), amino groups protected by isocyanate groups, amino groups and protecting groups, and protected by thiol groups and protecting groups. The thiol group etc. which were made are mentioned.
- a polymer block containing a hydroxyl group as a precursor structure is reacted with a compound having a partial structure (1) and a partial structure (carboxylic acid, ester, carbonyl halide, etc.) capable of reacting with a hydroxyl group, thereby reacting with a (meth) acrylic heavy polymer.
- a combined block (aA) or a (meth) acrylic polymer block (aB) can be formed.
- the polymer block containing a hydroxyl group protected by a protecting group as a precursor structure is converted to a hydroxyl group by removing the protecting group, and then the (meth) acrylic polymer block (aA) or (meth) acrylic A polymer block (aB) can be formed.
- the polymer block containing an isocyanate group as a precursor structure is reacted with a compound having a partial structure (1) and a partial structure capable of reacting with an isocyanate group (such as a hydroxyl group) to form a (meth) acrylic polymer block (aA).
- a compound having a partial structure (1) and a partial structure capable of reacting with an isocyanate group (such as a hydroxyl group) to form a (meth) acrylic polymer block (aA).
- an isocyanate group such as a hydroxyl group
- the polymer block containing an amino group as a precursor structure has a partial structure (1) and a partial structure capable of reacting with the amino group (carboxylic acid, carboxylic anhydride, ester, carbonyl halide, aldehyde group, isocyanate group, etc.).
- the (meth) acrylic polymer block (aA) or the (meth) acrylic polymer block (aB) can be formed.
- a polymer block containing an amino group protected by a protecting group as a precursor structure is similarly used after (meth) acrylic polymer block (aA) or (meth) after removing the protecting group to form an amino group.
- An acrylic polymer block (aB) can be formed.
- a polymer block containing a thiol group as a precursor structure includes a partial structure (1) and a partial structure capable of reacting with a thiol group (carboxylic acid, carboxylic acid anhydride, ester, carbonyl halide, isocyanate group, carbon-carbon double bond)
- the (meth) acrylic polymer block (aA) or the (meth) acrylic polymer block (aB) can be formed by reacting with a compound having the above.
- the polymer block containing a thiol group protected by a protecting group as a precursor structure is the same as the (meth) acrylic polymer block (aA) or (meth) after removing the protecting group to form a thiol group.
- An acrylic polymer block (aB) can be formed.
- the polymerization active terminal The (meth) acrylic diblock copolymer (B) can also be obtained by inactivating. If a (meth) acrylic triblock copolymer (A) is produced from a polymerization active terminal that is not deactivated by partially deactivating such polymerization active terminal, a (meth) acrylic triblock copolymer is produced.
- a mixture of (A) and a (meth) acrylic diblock copolymer (B) can be obtained, and the active energy ray-curable composition of the present invention can be efficiently produced.
- the method for deactivating the polymerization active terminal include a method of adding an appropriate amount of a known terminator (alcohol or the like), and a method of stirring for a predetermined time in a state where the monomers in the polymerization system are exhausted.
- the (meth) acrylic polymer block having the precursor structure and the (meth) acrylic polymer block (bA) are sequentially formed.
- the (meth) acrylic diblock copolymer (B) can also be obtained by a method of converting the precursor structure into the partial structure (1) after deactivating the polymerization active terminal.
- a precursor of a (meth) acrylic triblock copolymer (A) containing a precursor structure is produced from a polymerization active terminal that has not been deactivated by partially deactivating such a polymerization active terminal, )
- a mixture of the acrylic triblock copolymer (A) precursor and the methacrylic diblock copolymer (B) precursor can be obtained, and the active energy ray-curable composition of the present invention can be efficiently produced.
- As a method for deactivating the polymerization active terminal in the polymerization of the (meth) acrylic triblock copolymer (A), the polymerization active terminal is changed at the stage of forming the (meth) acrylic polymer block (aA). Deactivation is the same as in the case of obtaining the methacrylic diblock copolymer (B).
- (meth) acrylic polymer block (aA) or (meth) acrylic polymer As a method for forming the block (aB), a monomer containing di (meth) acrylate (3) is polymerized from the viewpoint that an active energy ray-curable group containing the partial structure (2) can be easily introduced directly.
- a method typically a method of living anionic polymerization, is preferred.
- the ratio m (A) / m (B) with (B) is not particularly limited, but is 99.5 from the viewpoint of the viscosity and curing rate of the active energy ray-curable composition and the flexibility of the resulting cured product. /0.5 to 50/50 is preferable, 99/1 to 60/40 is more preferable, and 98/2 to 70/30 is even more preferable.
- the ratio Mn (bB) / Mn (bA) with the number average molecular weight Mn (bA) per (meth) acrylic polymer block (bA) contained in the (meth) acrylic triblock copolymer (A) Is in the range of 0.2 to 2.0, and is preferably in the range of 0.25 to 1.9 from the viewpoint of developing flexibility while maintaining a low viscosity, A range is more preferred.
- the (meth) acrylic triblock copolymer (A) contains two (meth) acrylic polymer blocks (bA)
- the number average molecular weight of these two polymer blocks (bA) It is preferable that Mn (bB) / Mn (bA) satisfies the above range.
- Mn (Mn (A)) of (meth) acrylic triblock copolymer (A) and Mn of (meth) acrylic diblock copolymer (B) in the active energy ray-curable composition of the present invention is preferably in the range of 0.5 to 1000, more preferably in the range of 0.8 to 900, and 1.0 to 800. A range is further preferred.
- the active energy ray-curable composition of the present invention may further contain a photopolymerization initiator.
- a photopolymerization initiator include acetophenones (for example, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-hydroxy-2-methyl-1-phenylpropane).
- benzophenones eg, benzophenone, benzoylbenzoic acid, hydroxybenzophenone, 3,3′-dimethyl-4-methoxybenzophenone, acrylated benzophenone, etc.
- Michler ketones eg, Michler ketone
- benzoins Carbonyl compounds such as benzoin, benzoin methyl ether, benzoin isopropyl ether, etc .; sulfuration of tetramethylthiuram monosulfide, thioxanthones (eg, thioxanthone, 2-chlorothioxanthone, etc.)
- Phosphorus compounds such as acyl phosphine oxides (eg 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide); titanocenes ( Titanium compounds such as bis ( ⁇ 5 -2,4-cyclopentadie
- the content is based on 100 parts by mass of the total amount of the (meth) acrylic triblock copolymer (A) and the (meth) acrylic diblock copolymer (B). 0.01 to 10 parts by mass is preferable, and 0.05 to 8 parts by mass is more preferable. When the amount is 0.01 parts by mass or more, the curability of the active energy ray-curable composition becomes good, and when the amount is 10 parts by mass or less, the resulting cured product tends to have good heat resistance.
- the active energy ray-curable composition of the present invention may contain a sensitizer in addition to the photopolymerization initiator.
- the sensitizer include n-butylamine, di-n-butylamine, tri-n-butylphosphine, allylthiouric acid, triethylamine, diethylaminoethyl methacrylate and the like. Among these, diethylaminoethyl methacrylate and triethylamine are preferable.
- the mass ratio of the photopolymerization initiator to the sensitizer is usually 10:90 to 90:10, preferably 20:80 to 80:20. It is.
- the active energy ray-curable composition of the present invention is irradiated with active energy rays other than the (meth) acrylic triblock copolymer (A) and the (meth) acrylic diblock copolymer (B). May contain a reactive diluent exhibiting polymerizability.
- the reactive diluent is not particularly limited as long as it is a compound that exhibits polymerizability upon irradiation with active energy rays.
- Urethane acrylate resin obtained by reacting pentaerythritol triacrylate, etc.]; a resin in which a (meth) acrylic group is introduced into the above polyol via an ester bond; a polyester acrylate resin; an epoxidized soybean oil, an epoxy benzyl stearate And epoxy compounds.
- These reactive diluents may be used alone or in combination of two or more.
- the content is determined by the viscosity of the active energy ray-curable composition and the active energy ray-curable composition. From the viewpoint of mechanical properties of the cured product obtained by irradiation, the content is preferably 10 to 90% by mass, and more preferably 20 to 80% by mass.
- the active energy ray-curable composition of the present invention has an active energy ray-curable property such as a plasticizer, a tackifier, a softener, a filler, a stabilizer, a pigment, and a dye as long as the curability is not significantly inhibited.
- an active energy ray-curable property such as a plasticizer, a tackifier, a softener, a filler, a stabilizer, a pigment, and a dye as long as the curability is not significantly inhibited.
- Various additives having no group may be contained.
- the purpose of including the plasticizer in the active energy ray-curable composition of the present invention is, for example, adjustment of the viscosity of the active energy ray-curable composition, a cured product obtained by curing the active energy ray-curable composition. Is the adjustment of the mechanical strength.
- plasticizer examples include phthalic acid esters such as dibutyl phthalate, diheptyl phthalate, di (2-ethylhexyl) phthalate, and butyl benzyl phthalate; Aliphatic dibasic acid esters; aliphatic esters such as butyl oleate and methyl acetylricinoleate; esters of polyalkylene glycols such as diethylene glycol dibenzoate, triethylene glycol dibenzoate and pentaerythritol ester; tricresyl phosphate, tributyl phosphate, etc.
- phthalic acid esters such as dibutyl phthalate, diheptyl phthalate, di (2-ethylhexyl) phthalate, and butyl benzyl phthalate
- Aliphatic dibasic acid esters such as butyl oleate and methyl acetylricinoleate
- Trimellitic acid ester Diene (co) polymer such as polybutadiene, butadiene-acrylonitrile copolymer, polychloroprene; Polyisobutylene; chlorinated paraffins; hydrocarbon oils such as alkyldiphenyls and partially hydrogenated terphenyls; process oils; polyether polyols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol and the hydroxyl groups of these polyether polyols Polyethers such as derivatives converted to ester groups, ether groups, etc .; dibasic acids such as sebacic acid, adipic acid, azelaic acid, phthalic acid, and ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, etc. Examples include polyesters obtained from dihydric alcohols. These plasticizers may be used alone or in combination of two or more.
- the content thereof is (meth) acrylic triblock copolymer (A) and (meth) acrylic diblock copolymer (B).
- From 5 to 150 parts by weight preferably from 10 to 120 parts by weight, more preferably from 20 to 100 parts by weight based on 100 parts by weight of the total amount of
- By adjusting the amount to 5 parts by mass or more effects such as physical property adjustment and property adjustment become remarkable, and by setting the amount to 150 parts by mass or less, a cured product obtained by curing the active energy ray-curable composition tends to have excellent mechanical strength. .
- the molecular weight or Mn (number average molecular weight) of these plasticizers is preferably 400 to 15000, more preferably 800 to 10,000, and more preferably 1000 to 8,000.
- a plasticizer may or may not have a functional group other than the active energy ray curable group (for example, a hydroxyl group, a carboxyl group, a halogen group, etc.).
- the molecular weight or Mn of the plasticizer is 400 or more, the plasticizer does not flow out from the cured product of the active energy ray-curable composition with time, and the initial physical properties can be maintained for a long time.
- the molecular weight or Mn of the plasticizer is 15000 or less, the handleability of the active energy ray-curable composition tends to be improved.
- the purpose of including the tackifier in the active energy ray-curable composition of the present invention is to impart tackiness to a cured product obtained from the composition, for example.
- the tackifier include coumarone / indene resin, phenol resin, pt-butylphenol / acetylene resin, phenol / formaldehyde resin, xylene / formaldehyde resin, aromatic hydrocarbon resin, aliphatic hydrocarbon resin (terpene resin, etc.) Styrene resin (polystyrene, poly- ⁇ -methylstyrene, etc.), polyhydric alcohol ester of rosin, hydrogenated rosin, hydrogenated wood rosin, ester of hydrogenated rosin and monoalcohol or polyhydric alcohol, terpine tackifying resin And the like.
- aliphatic hydrocarbon resins pene resins and the like
- polyhydric alcohol esters of rosin hydrogenated rosin, hydrogenated wood rosin, esters of hydrogenated rosin and monoalcohol or polyhydric alcohol are preferable.
- the additive having no active energy ray-curable group may be an organic compound or an inorganic compound.
- the active energy ray can be irradiated using a known apparatus.
- the acceleration voltage is suitably 0.1 to 10 MeV
- the irradiation dose is suitably 1 to 500 kGy.
- a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a carbon arc lamp, a metal halide lamp, a xenon lamp, a chemical lamp, an LED, or the like that emits light in a wavelength range of 150 to 450 nm can be used.
- Integrated light quantity of the active energy ray is usually in the range of 10 ⁇ 20000mJ / cm 2, preferably in the range of 30 ⁇ 5000mJ / cm 2.
- the amount is less than 10 mJ / cm 2
- the curability of the active energy ray-curable composition tends to be insufficient, and when it exceeds 20000 mJ / cm 2 , the active energy ray-curable composition may be deteriorated.
- the relative humidity when irradiating the active energy ray-curable composition of the present invention with active energy rays is preferably 30% or less from the viewpoint of suppressing the decomposition of the active energy ray-curable composition. % Or less is more preferable.
- the active energy ray-curable composition of the present invention can be further heated during the active energy ray irradiation or after irradiation to accelerate the curing as necessary.
- a heating temperature is preferably in the range of 40 to 130 ° C, more preferably in the range of 50 to 100 ° C.
- the active energy ray-curable composition of the present invention can be easily applied to a cured product and a substrate when it needs to be disposed of after being applied to a substrate such as an adhesive or a coating material and cured. Can be separated and separated.
- the peeling method the wet heat decomposition method is preferable from the viewpoint of workability and economy.
- the wet heat decomposition temperature is preferably from 100 to 250 ° C, more preferably from 130 to 220 ° C.
- the wet pyrolysis relative humidity is preferably 10 to 100%, more preferably 30 to 100%.
- the wet heat decomposition time is preferably 1 minute to 24 hours, more preferably 1 minute to 5 hours, and even more preferably 1 minute to 2 hours.
- Applications of the active energy ray-curable composition of the present invention include curable resins and adhesives used in fields such as automobiles, home appliances, architecture, civil engineering, sports, displays, optical recording equipment, optical equipment, semiconductors, batteries, and printing.
- More specific examples of these uses include adhesives for polypropylene, metals, and wood (hot melt adhesives, photo-curable adhesives); Sealing materials for hard disk drives (HDD), construction, automobiles, electrical / electronic parts for flexible printed electronics (backside of solar cells, etc.); Sealing materials for HDD, construction, automobile, flexible printed electronics, electrical / electronic parts (backside of solar cells, etc.), etc.
- Electrical insulation materials such as insulation coatings for electric wires and cables; Coating materials such as metallized film undercoat, hard coat, optical fiber coat, etc .; LED curable ink, UV curable ink, electron beam curable ink, ink for inkjet equipment, etc .; for automobiles, railway vehicles, aircraft, industrial Gaskets, packings, anti-vibration rubber, anti-corrosion materials, anti-vibration materials for glass, sealing materials for meshed glass and laminated glass end faces (cut parts), wind seal gaskets, door glass gaskets, and other airtight seals Material; Ship applications such as damping materials for engine rooms and measurement rooms; Automotive applications such as engines (oil pans, front covers, rocker covers), car bodies (dashes, floors, doors, roofs, panels, wheel houses), tarance missions, parking brake covers, and damping materials for seat backs; Chassis components such as vibration and soundproof engines and suspension rubber (especially engine mount rubber); Engine parts such as hoses for cooling, fuel supply, exhaust control, and engine oil seals
- Waterproof packing, heater packing, electrode packing, safety valve diaphragm, hoses for sake cans, waterproof packing, solenoid valve, waterproof packing for steam microwave oven and jar rice cooker, water tank packing, water absorption valve, water receiving packing, Connection hose, belt, insulation heater packing, steam outlet seal, etc., oil packing for combustion equipment, O-ring, drain packing, pressure tube, blower tube, feed / intake packing, anti-vibration rubber, oil filler packing, oil Loudspeaker gaskets, sound pipes, diaphragm valves, air pipes, etc.
- Sports floors all-weather pavement materials, gymnasium floors, etc.
- sports shoe components shoe sole materials, midsole materials, etc.
- ball balls golf balls, etc.
- Architectural applications such as roofs, floors, shutters, curtain rails, floors, piping ducts, deck plates, curtain walls, stairs, doors, vibration isolator, structural damping materials
- Structural materials rubber expansion joints, bearings, waterproof plates, waterproof sheets, rubber dams, elastic pavements, anti-vibration pads, protective bodies, etc.
- construction sub-materials rubber molds, rubber packers, rubber skirts, etc.
- Sponge mats mortar hoses, mortar strainers, etc.
- construction auxiliary materials rubber sheets, air hoses, etc.
- safety measures rubber buoys, wave-dissipating materials, etc.
- environmental protection products oil fences, silt fences, antifouling materials, marine) Hose, draging hose, oil skimmer, etc.
- the raw material was dried and purified by a conventional method and degassed with nitrogen, and the transfer and supply were performed in a nitrogen atmosphere.
- the consumption rate of each monomer after polymerization was calculated by the following method. That is, 0.5 ml of a polymerization reaction solution collected from the polymerization system is placed in 0.5 ml of methanol to prepare 1.0 ml of a mixed solution, and 0.1 ml of the obtained mixed solution is dissolved in 0.5 ml of deuterated chloroform.
- Eluent Tetrahydrofuran eluent Flow rate: 0.35 ml / min
- Column temperature 40 ° C
- Detection method differential refractive index (RI) [Polymerization initiation efficiency]
- Mn (R1) the number average molecular weight of the polymer obtained in the following step (1)
- the polymerization initiation efficiency is 100%
- the Mn (calculated value) of the polymer obtained in the step (1) is Mn ( If I1)
- the polymerization initiation efficiency (F1) in step (1) is calculated from the following equation.
- F2 (%) 10000 ⁇ ⁇ Mn (I2) ⁇ Mn (I1) ⁇ / [F1 ⁇ ⁇ Mn (R2) ⁇ Mn (R1) ⁇ ] [Mn of polymer block (bA) and polymer block (bB)]
- the number average molecular weight (Mn (R2)) of the block copolymer obtained in the step (2) and the number average molecular weight of the polymer obtained in the step (1) were used as the difference value of (Mn (R1)).
- the consumption rate of 2- (trimethylsilyloxy) ethyl methacrylate and methyl methacrylate in step (1) was 100%.
- Mn (Mn (R1)) of the obtained polymer was 1,300, and Mw / Mn was 1.15.
- the polymerization initiation efficiency (F1) in the step (1) was 98%.
- the consumption rate of n-butyl acrylate in step (2) was 100%.
- Mn (Mn (R2)) of the obtained polymer was 21,300 and Mw / Mn was 1.18.
- the block efficiency (F2) from the step (1) to the step (2) was 100%.
- the consumption rate of 2- (trimethylsilyloxy) ethyl methacrylate and methyl methacrylate in step (3) was 100%. Moreover, Mn of the obtained polymer was 22,800 and Mw / Mn was 1.17.
- Mn of the obtained (meth) acrylic triblock copolymer (A1) was 23,100, Mw / Mn was 1.19, and the content of the partial structure (1) was 3.7 mol%.
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (1) was 100%.
- Mn (Mn (R1)) of the obtained polymer was 1,340, and Mw / Mn was 1.16.
- the polymerization initiation efficiency (F1) in the step (1) was 99%.
- the consumption rate of n-butyl acrylate in step (2) was 100%.
- Mn (Mn (R2)) of the obtained polymer was 21,300 and Mw / Mn was 1.18.
- the block efficiency (F2) from the step (1) to the step (2) was 100%.
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (3) was 100%.
- Mn of the obtained (meth) acrylic triblock copolymer (A2) was 22,600, Mw / Mn was 1.19, and the content of the partial structure (1) was 3.7 mol%.
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (1) was 100%.
- Mn (Mn (R1)) of the polymer obtained at the process (1) was 1,780, and Mw / Mn was 1.15.
- the polymerization initiation efficiency (F1) in the step (1) was 98%.
- the consumption rate of n-butyl acrylate in step (2) was 100%.
- Mn (Mn (R2)) of the obtained polymer was 44,600, and Mw / Mn was 1.18.
- the block efficiency (F2) from the step (1) to the step (2) was 100%.
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (3) was 100%.
- Mn of the obtained (meth) acrylic triblock copolymer (A3) was 46,300, Mw / Mn was 1.23, and the content of the partial structure (1) was 3.9 mol%.
- the consumption rate of 2- (trimethylsilyloxy) ethyl methacrylate and methyl methacrylate in step (1) was 100%.
- Mn (Mn (R1)) of the obtained polymer was 1,300, and Mw / Mn was 1.15.
- the polymerization initiation efficiency (F1) in the step (1) was 98%.
- the consumption rate of n-butyl acrylate in step (2) was 100%.
- Mn (Mn (R2)) of the obtained polymer was 21,300 and Mw / Mn was 1.18.
- the block efficiency (F2) from the step (1) to the step (2) was 100%.
- Mn of the obtained (meth) acrylic diblock copolymer (B1) was 21500, Mw / Mn was 1.17, and the content of the partial structure (1) was 2.1 mol%.
- step (1) the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate was 100%. Moreover, Mn (Mn (R1)) of the polymer obtained at the process (1) was 1,380, and Mw / Mn was 1.18. Furthermore, the polymerization initiation efficiency (F1) in the step (1) was 99%. Furthermore, the polymerization initiation efficiency (F1) in the step (1) was 99%.
- the consumption rate of n-butyl acrylate in step (2) was 100%. Furthermore, the block efficiency (F2) from the step (1) to the step (2) was 100%. Moreover, Mn of the obtained (meth) acrylic diblock copolymer (B2) was 21,600, Mw / Mn was 1.19, and the content of the partial structure (1) was 2.1 mol%. .
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (1) was 100%.
- Mn of the obtained polymer was 1,810 and Mw / Mn was 1.15.
- the polymerization initiation efficiency (F1) was 98%.
- the consumption rate of n-butyl acrylate in step (2) was 100%. Furthermore, the block efficiency (F2) from the step (1) to the step (2) was 100%. Moreover, Mn of the obtained (meth) acrylic diblock copolymer (B3) was 44,800, Mw / Mn was 1.17, and the content of the partial structure (1) was 2.2 mol%. .
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (1) was 100%.
- Mn (Mn (R1)) of the polymer obtained at the process (1) was 1,410, and Mw / Mn was 1.15.
- the polymerization initiation efficiency (F1) in the step (1) was 99%.
- Process (2) Subsequently, while stirring the reaction solution at ⁇ 20 ° C., 31.8 ml (14.14 ml) of a 0.450 mol / L toluene solution of isobutylbis (2,6-di-t-butyl-4-methylphenoxy) aluminum as the organoaluminum compound.
- step (2) The consumption rate of n-butyl acrylate in step (2) was 100%. Moreover, Mn (Mn (R2)) of the obtained block copolymer was 21,500, and Mw / Mn was 1.19. Furthermore, the block efficiency (F2) from the step (1) to the step (2) was 100%. (Process (3)) Subsequently, after the reaction solution was further stirred at ⁇ 20 ° C. for 20 minutes, as monomers, 16.3 ml (67.8 mmol) of 1,1-dimethylpropane-1,3-diol dimethacrylate and 14.4 ml (136 mmol) of methyl methacrylate were used.
- composition obtained by mixing the (meth) acrylic triblock copolymer (A2) and the (meth) acrylic diblock copolymer (B2) at a known ratio was subjected to GPC (gel permeation chromatography, HLC-8220 GPC).
- step (1) 20.0 ml of a mixture of 16.4 ml (68.4 mmol) of 1,1-dimethylpropane-1,3-diol dimethacrylate and 3.63 ml (34.1 mmol) of methyl methacrylate was added as a monomer. Then, except that 438 ml (3.05 mol) of n-butyl acrylate is added as a monomer in step (2) at a rate of 5 ml / min, steps (1) and (2) are carried out in the same manner as in Synthesis Example 6. Then, 100 ml of methanol was added at ⁇ 20 ° C. while stirring the reaction solution to stop anionic polymerization.
- the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate in step (1) was 100%.
- Mn of the obtained polymer was 1,560 and Mw / Mn was 1.14.
- the polymerization initiation efficiency (F1) was 98%.
- the consumption rate of n-butyl acrylate in step (2) was 100%. Furthermore, the block efficiency (F2) from the step (1) to the step (2) was 100%. Moreover, Mn of the obtained (meth) acrylic-type diblock copolymer (B4) was 38,500, Mw / Mn was 1.17, and content of the partial structure (1) was 2.2 mol%. .
- Step (1) and Step (2) were performed in the same manner as in Synthesis Example 2 except that 150 ml (1.0 mol) of n-butyl acrylate was added as a monomer in Step (2) at a rate of 10 ml / min. After that, the anionic polymerization was stopped by adding 100 ml of methanol at ⁇ 20 ° C. while stirring the reaction solution. The obtained solution was poured into 10 L of methanol, the polymer was precipitated, recovered by filtration, dried at 100 ° C. and 30 Pa, and 132 g of (meth) acrylic diblock copolymer (B) (hereinafter referred to as “( (Meth) acrylic diblock copolymer (B5) ”).
- (meth) acrylic diblock copolymer (B5) hereinafter referred to as “( (Meth) acrylic diblock copolymer (B5) ”).
- step (1) the consumption rate of 1,1-dimethylpropane-1,3-diol dimethacrylate and methyl methacrylate was 100%. Moreover, Mn (Mn (R1)) of the polymer obtained at the process (1) was 1320, and Mw / Mn was 1.18. Furthermore, the polymerization initiation efficiency (F1) in the step (1) was 99%. Furthermore, the polymerization initiation efficiency (F1) in the step (1) was 99%.
- the consumption rate of n-butyl acrylate in step (2) was 100%. Furthermore, the block efficiency (F2) from the step (1) to the step (2) was 100%. Moreover, Mn of the obtained (meth) acrylic diblock copolymer (B5) was 7,200, Mw / Mn was 1.19, and the content of the partial structure (1) was 6.3 mol%. .
- the number average molecular weight of the (meth) acrylic polymer block having an active energy ray-curable group containing the partial structure (1) contained in the block copolymers obtained in Synthesis Examples 1 to 9 is shown in Table 1 below. To summarize.
- Example 1 90 parts by mass of the (meth) acrylic triblock copolymer (A1) obtained in Synthesis Example 1 as the (meth) acrylic triblock copolymer (A), and the (meth) acrylic diblock copolymer ( B) 100 parts by weight of a polymer component consisting of 10 parts by weight of the (meth) acrylic diblock copolymer (B1) obtained in Synthesis Example 4, 2 parts by weight of 1-hydroxycyclohexyl phenyl ketone as a photopolymerization initiator, In addition, 100 parts by mass of toluene as a solvent was mixed to prepare a solution. After removing most of the toluene from the obtained solution at 20 ° C.
- the toluene was further completely removed at 70 ° C. and 30 Pa under reduced pressure to obtain an active energy ray-curable composition.
- the viscosity of the obtained active energy ray-curable composition, the curing rate, and the elastic modulus of the cured product were evaluated by the following methods. The evaluation results are shown in Table 2.
- the viscosity of the active energy ray-curable composition was measured using MARS III manufactured by HAAKE. A steady flow viscosity measurement mode is used as a measurement mode, an active energy ray-curable composition is placed on a ⁇ 35 mm, 1 ° inclined cone plate, a measurement temperature is 25 ° C., a measurement gap is 0.05 mm, and a shear rate is 1 (1 / s ) (Pa ⁇ s) was measured under the measurement conditions.
- the curing rate of the active energy ray-curable composition was evaluated using MARS III manufactured by HAAKE.
- a high-speed OSC time-dependent measurement mode is used as a measurement mode, an active energy ray-curable composition is coated on a ⁇ 20 mm parallel plate at a thickness of 50 ⁇ m, a measurement temperature is 25 ° C., a measurement gap is 0.15 mm, and a measurement frequency is 5 Hz.
- the viscoelasticity measurement is performed while irradiating a UV lamp (Omni Cure series 2000 manufactured by Lumen Dynamics, irradiation intensity 150 mW / cm 2 ), and the storage shear modulus (G ′) and the loss shear modulus (G ′′) are crossed. The overtime was measured and used as an index of curing speed.
- Example 2 (Examples 2 to 5, 7 to 9) Except for changing the type and amount of the (meth) acrylic triblock copolymer (A) and the type and amount of the (meth) acrylic diblock copolymer (B) as described in Table 2, An active energy ray-curable composition was prepared in the same manner as in Example 1, and the viscosity, the curing rate, and the elastic modulus of the cured product were evaluated. The evaluation results are shown in Table 2.
- Example 6 An active energy ray-curable composition is prepared in the same manner as in Example 1 except that 100 parts by mass of the polymer component is changed to 100 parts by mass of the polymer composition (C1), and the viscosity of the active energy ray-curable composition is obtained. Then, the curing speed and the elastic modulus of the cured product were evaluated. The evaluation results are shown in Table 2.
- the active energy ray-curable compositions obtained in Reference Examples 1 to 3 are cured products having low viscosity and excellent flexibility, similar to the active energy ray-curable compositions obtained in Examples 1 to 9. Although obtained, the curing rate is low compared to the examples.
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Abstract
Description
[1]下記一般式(1)で示される部分構造(以下「部分構造(1)」と称する)を含む活性エネルギー線硬化性基を有する(メタ)アクリル系重合体ブロック(aA)および活性エネルギー線硬化性基を有さない(メタ)アクリル系重合体ブロック(bA)を含有する(メタ)アクリル系トリブロック共重合体(A)と、部分構造(1)を含む活性エネルギー線硬化性基を有する(メタ)アクリル系重合体ブロック(aB)および活性エネルギー線硬化性基を有さない(メタ)アクリル系重合体ブロック(bB)を含有する(メタ)アクリル系ジブロック共重合体(B)とを含有し、かつ前記(メタ)アクリル系ジブロック共重合体(B)に含まれる(メタ)アクリル系重合体ブロック(bB)の数平均分子量Mn(bB)と前記(メタ)アクリル系トリブロック共重合体(A)に含まれる(メタ)アクリル系重合体ブロック(bA)1個あたりの数平均分子量Mn(bA)との比率Mn(bB)/Mn(bA)が0.2~2.0の範囲である活性エネルギー線硬化性組成物;
[2]さらに、光重合開始剤を含有してなる、上記[1]の活性エネルギー線硬化性組成物;並びに
[3](メタ)アクリル系トリブロック共重合体(A)および(メタ)アクリル系ジブロック共重合体(B)が有する上記活性エネルギー線硬化性基が下記一般式(2)で示される部分構造(以下「部分構造(2)」と称する)を含む、上記[1]または[2]の活性エネルギー線硬化性組成物;
を提供することにより達成される。
上記一般式(1)中、R1が表す炭素数1~20の炭化水素基としては、例えば、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、t-ブチル基、2-メチルブチル基、3-メチルブチル基、2-エチルブチル基、3-エチルブチル基、2,2-ジメチルブチル基、2,3-ジメチルブチル基、n-ペンチル基、ネオペンチル基、n-ヘキシル基、2-メチルペンチル基、3-メチルペンチル基、n-デシル等のアルキル基;シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等のシクロアルキル基;フェニル基、ナフチル基等のアリール基;ベンジル基、フェニルエチル基などのアラルキル基が挙げられる。中でも、活性エネルギー線硬化性の観点から、メチル基およびエチル基が好ましく、メチル基が最も好ましい。
一般式(2)中、R1が表す炭素数1~20の炭化水素基の具体例および好適例としては、上記一般式(1)のR1と同様の炭化水素基が挙げられる。
上記一般式(3)中、R2およびR3となり得る炭素数1~6の炭化水素基としては、上記一般式(2)のR2およびR3と同様の基が挙げられる。上記一般式(3)中、nは、活性エネルギー線硬化性組成物の流動性および硬化速度の観点から2~5であることが好ましい。
(式中、R7は一価の飽和炭化水素基、一価の芳香族炭化水素基、アルコキシ基、アリールオキシ基またはN,N-二置換アミノ基を表し、R8およびR9はそれぞれ独立してアリールオキシ基を表すか、あるいはR8およびR9は互いに結合してアリーレンジオキシ基を形成している)
AlR10(R11)(R12) (A-2)
(式中、R10はアリールオキシ基を表し、R11およびR12はそれぞれ独立して一価の飽和炭化水素基、一価の芳香族炭化水素基、アルコキシ基またはN,N-二置換アミノ基を表す)
上記一般式(A-1)および(A-2)中、R7、R8、R9およびR10がそれぞれ独立して表すアリールオキシ基としては、例えばフェノキシ基、2-メチルフェノキシ基、4-メチルフェノキシ基、2,6-ジメチルフェノキシ基、2,4-ジ-t-ブチルフェノキシ基、2,6-ジ-t-ブチルフェノキシ基、2,6-ジ-t-ブチル-4-メチルフェノキシ基、2,6-ジ-t-ブチル-4-エチルフェノキシ基、2,6-ジフェニルフェノキシ基、1-ナフトキシ基、2-ナフトキシ基、9-フェナントリルオキシ基、1-ピレニルオキシ基、7-メトキシ-2-ナフトキシ基等が挙げられる。
ハードディスクドライブ(HDD)用、建築用、自動車用、フレキシブルプリンテッドエレクトロニクス用電気・電子部品(太陽電池裏面等)用等のシーリング材;
HDD用、建築用、自動車用、フレキシブルプリンテッドエレクトロニクス用、電気・電子部品(太陽電池裏面等)用などの防錆・防湿・防水用等の封止材;
電線・ケーブル用絶縁被覆材等の電気絶縁材料;
金属蒸着膜アンダーコート、ハードコート、光ファイバコート等のコーティング材;LED硬化性インク、UV硬化性インク、電子線硬化性インク、インクジェット機器用等のインク;自動車用、鉄道車両、航空機、工業用のガスケット、パッキン類、防振ゴム、防舷材、ガラスの振動防止材、網入りガラスや合わせガラス端面(切断部)の封止材、ウインドシールガスケット、ドアガラス用ガスケットなどの気密保持用シール材;
エンジンルーム、計測ルーム用制振材等の船舶用途;
エンジン(オイルパン、フロントカバー、ロッカーカバー)、車体(ダッシュ、フロア、ドア、ルーフ、パネル、ホイルハウス)、タランスミッション、パーキングブレーキカバー、シートバック用制振材等の自動車用途;
防振、防音用のエンジンおよびサスペンジョンゴム(特にエンジンマウントラバー)等のシャーシ部品;
冷却用、燃料供給用、排気制御用等のホース類、エンジンオイル用シール材等のエンジン部品;
排ガス清浄装置部品;
ブレーキ部品;
家電用のパッキン、Oリング、ベルト等(照明器具用の飾り類、防水パッキン類、防振ゴム類、防虫パッキン類、クリーナ用の防振・吸音と空気シール材、電気温水器用の防滴カバー、防水パッキン、ヒータ部パッキン、電極部パッキン、安全弁ダイアフラム、酒かん器用のホース類、防水パッキン、電磁弁、スチームオーブンレンジおよびジャー炊飯器用の防水パッキン、給水タンクパッキン、吸水バルブ、水受けパッキン、接続ホース、ベルト、保温ヒータ部パッキン、蒸気吹き出し口シール等、燃焼機器用のオイルパッキン、Oリング、ドレインパッキン、加圧チューブ、送風チューブ、送・吸気パッキン、防振ゴム、給油口パッキン、油量計パッキン、送油管、ダイアフラム弁、送気管等、音響機器用のスピーカーガスケット、スピーカーエッジ、ターンテーブルシート、ベルト、プーリー等);
建築分野用の、構造用ガスケット(ジッパーガスケット)、空気膜構造屋根材、防水材、定形シーリング材、防振材、防音材、セッティングブロック、摺動材等;
スポ―ツ用の、スポーツ床(全天候型舗装材、体育館床等)、スポーツシューズ部材(靴底材、中底材等)、球技用ボール(ゴルフボール等);
ルーフ、フロア、シャッタ、カーテンレール、床、配管ダクト、デッキプレート、カーテンウォール、階段、ドア、免振アイソレーター、構造材用制振材等の建築用途;
土木分野用の、構造用材料(ゴム伸縮継手、支承、止水板、防水シート、ラバーダム、弾性舗装、防振パット、防護体等)、工事副材料(ゴム型枠、ゴムパッカー、ゴムスカート、スポンジマット、モルタルホース、モルタルストレーナ等)、工事補助材料(ゴムシート類、エアホース等)、安全対策商品(ゴムブイ、消波材等)、環境保全商品(オイルフェンス、シルトフェンス、防汚材、マリンホース、ドレッジングホース、オイルスキマー等)等;
液晶ディスプレイ、カラーPDP(プラズマディスプレイ)、プラズマアドレス液晶(PALC)ディスプレイ、有機EL(エレクトロルミネッセンス)ディスプレイ、有機TFT(有機薄膜トランジスタ)ディスプレイ、フィールドエミッションディスプレイ(FED)、電子ペーパー、タッチパネル、携帯電話のディスプレイ、カーナビのディスプレイなどのディスプレイ用の封止材、接着剤、光学弾性樹脂(OCR)、光学透明接着剤(OCA)、充填材;
ビデオディスク(VD)、CD、CD-ROM、CD-R、CD-RW、DVD、DVD-ROM、DVD-R、DVD-RW、BD、BD-ROM、BD-R、BD-RE、MO、MD、相変化ディスク(PD)、ホログラム、光カード用のディスク基板材料、ピックアップレンズ、保護フィルム、封止材、接着剤;
光学機器(スチルカメラ、ビデオカメラ、プロジェクター、光センサ)のレンズ、ファインダプリズム、光ファイバ、ターゲットプリズム、ファインダーカバー、受光センサー部、保護フィルム、フェルール、封止材、接着剤;
素子の封止材、前面ガラスの保護フィルム、接着剤などの太陽電池部材;
ステッピングモーター、磁気ディスク、ハードディスク、食器洗浄機、乾燥機、洗濯機、ファンヒーター、ミシン、自動販売機、スピーカフレーム、BSアンテナ、VTRカバー用制振材等の電気・電子機器用途;
テレビカメラ、複写機、電算機、プリンタ、レジスタ、キャビネット用制振材等のカメラ・事務機器用途;
光電子集積回路(OEIC)周辺の基板材料;
ヒートスプレッダー;
発熱材料とヒートスプレッダー、ヒートスプレッダーと冷却部材、との間にある熱を伝えるサーマルインターフェイス;
ヒーター、温度センサ、CPU、トランジスタなどの電子部品等の高温部品;
放熱フィン等のヒートシンク等、グラファイトシート(グラファイトフィルム)、液体セラミックスやペルチェ素子等の冷却部材;
熱伝導性材料;
家電、自動車周辺のエレクトロニクス分野(回路のパターン形成、プリント基板上の半田付け時の耐熱被覆等用等)等で用いる半導体回路用の半導体レジスト(UVレジスト、DeepUVレジスト、EBレジスト、電着レジスト、ドライフィルムレジスト);
プリント配線基板用の液状ソルダーレジスト;
プリント基板、ビルドアップ基板、立体回路基板用の電着レジスト;
片面・両面・多層基板の回路形成用のドライフィルムレジスト;
TFT配線用、カラーフィルター用等の液晶用フォトレジスト等;
絶縁コーティングの様な永久レジスト用途;等のレジスト用途;
半導体向けダイシングテープ用、ダイボンディングテープ用の粘接着剤;
LSI、超LSI材料用のマイクロリソグラフィー用のレジスト材料;
LEDの封止材、ダイボンド材、リフレクターや放熱性能を備えた基板上にLEDを配置した基板の封止材;
装飾ディスプレイ用照明;
標識類;
シュータ、エレベータ、エスカレータ、コンベア、トラクタ、ブルドーザ、発電機、コンプレッサ、コンテナ、ホッパ、防音ボックス、草刈り機のモータカバー用制振材等の産業機械関係用途;鉄道車両ルーフ、側板、ドア、アンダーフロア、各種補機カバー、橋梁用制振材等の鉄道用途;半導体用途の精密除振装置用制振材等の防振・制振・防音・免震材料;
断熱材、クッション材、吸音材、防振材、人工皮革、注型材料、成形材料、ポッティング材等の発泡剤;
ゴルフシャフト釣り竿およびボート等のレジャー用途、FRP用途、自動車、航空機、宇宙用途等、回転機・変圧器・制御器の層間材絶縁用途、工業製品および電子部品接着用等に用いるプリプレグ;
等が挙げられる。
重合後の各単量体の消費率は、以下の方法により算出した。すなわち、重合系中から採取した重合反応液0.5mlをメタノール0.5ml中に入れ混合液1.0mlを作製し、得られた混合液0.1mlを、重水素化クロロホルム0.5mlに溶解させて1H-NMR測定を行い、単量体として用いた(メタ)アクリル酸エステルの炭素-炭素二重結合に直結するプロトンに由来するピーク(化学シフト値6.08~6.10)および溶媒として用いたトルエンの芳香環に直結するプロトンに由来するピーク(化学シフト値7.00~7.38ppm)の積分値の比率の変化から算出した。
1H-NMR測定装置および条件
装置:日本電子株式会社製核磁気共鳴装置 「JNM-ECX400」
温度:25℃
[数平均分子量(Mn)、分子量分布(Mw/Mn)]
得られた重合体のGPC(ゲルパーミエーションクロマトグラフィー)測定を行い、標準ポリスチレン換算の数平均分子量(Mn)、重量平均分子量(Mw)、および分子量分布(Mw/Mn)の値を求めた。
GPC測定装置および条件
装置:東ソー株式会社製GPC装置「HLC-8220GPC」
分離カラム:東ソー株式会社製「TSKgel SuperMultiporeHZ-M(カラム径=4.6mm、カラム長=15cm)」(2本を直列に繋いで使用)
溶離液:テトラヒドロフラン
溶離剤流量:0.35ml/分
カラム温度:40℃
検出方法:示差屈折率(RI)
[重合開始効率]
下記工程(1)で得られた重合体の数平均分子量をMn(R1)とし、重合開始効率が100%である場合に工程(1)で得られる重合体のMn(計算値)をMn(I1)とすると、工程(1)における重合開始効率(F1)は以下の式から算出される。
[工程(1)から工程(2)にかけてのブロック効率]
下記工程(2)で得られたブロック共重合体の数平均分子量をMn(R2)とし、重合開始効率が100%である場合に工程(2)で得られるブロック共重合体のMn(計算値)をMn(I2)とすると、工程(1)から工程(2)にかけてのブロック効率(F2)は以下の式から算出される。
[重合体ブロック(bA)および重合体ブロック(bB)のMn]
工程(2)で得られたブロック共重合体の数平均分子量(Mn(R2))と工程(1)で得られた重合体の数平均分子量を(Mn(R1))の差の値とした。
得られた(メタ)アクリル系トリブロック共重合体(A)または(メタ)アクリル系ジブロック共重合体(B)を、重水素化クロロホルム0.5mlに溶解させて1H-NMR測定を行い、各ピークの積分値の比率から算出した。
(工程(1))
内部を乾燥し、窒素置換した3Lのフラスコに、トルエン1.5Lを添加したのち、フラスコ内の溶液を攪拌しながら、ルイス塩基として1,1,4,7,10,10-ヘキサメチルトリエチレンテトラミン7.4ml(27.3mmol)、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液63.6ml(28.6mmol)を順次添加したのち、-20℃に冷却した。これに有機リチウム化合物としてsec-ブチルリチウムの1.30mol/Lシクロヘキサン溶液20ml(26.0mmol)を加え、単量体としてメタクリル酸2-(トリメチルシリルオキシ)エチル17ml(78mmol)およびメタクリル酸メチル16.6ml(156mmol)の混合物33.6mlを一括で添加し、アニオン重合を開始した。単量体の添加終了から80分後に重合反応液は当初の黄色から無色に変わった。さらに20分撹拌後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液を31.8ml(14.3mmol)加え、その1分後に単量体としてアクリル酸n-ブチル504ml(3.5mol)を10ml/分の速度で添加した。単量体の添加終了直後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、単量体としてメタクリル酸2-(トリメチルシリルオキシ)エチル14.8ml(67.8mmol)およびメタクリル酸メチル14.4ml(136mmol)の混合物29.2mlを一括で添加したのち、2℃/分の速度で20℃に昇温した。単量体の添加終了から60分後に反応液をサンプリングした。
引き続き反応液を20℃で撹拌しつつ、メタノール100mlを添加することにより、アニオン重合を停止させた。
(工程(1))
内部を乾燥し、窒素置換した3Lのフラスコに、トルエン1.5Lを添加したのち、フラスコ内の溶液を攪拌しながら、ルイス塩基として1,1,4,7,10,10-ヘキサメチルトリエチレンテトラミン7.4ml(27.3mmol)、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液63.6ml(28.6mmol)を順次添加したのち、-20℃に冷却した。これに有機リチウム化合物としてsec-ブチルリチウムの1.30mol/Lシクロヘキサン溶液20ml(26.0mmol)を加え、単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート18.7ml(78mmol)とメタクリル酸メチル16.6ml(156mmol)との混合物35.3mlを一括で添加し、アニオン重合を開始した。混合物の添加終了後から80分後に重合反応液は当初の黄色から無色に変わった。さらに20分撹拌後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液を31.8ml(14.3mmol)加え、その1分後に単量体としてアクリル酸n-ブチル504ml(3.5mol)を10ml/分の速度で添加した。単量体の添加終了直後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート16.3ml(67.8mmol)とメタクリル酸メチル14.4ml(136mmol)の混合物30.7mlを一括で添加したのち、2℃/分の速度で20℃に昇温した。単量体の添加終了から60分後に反応液をサンプリングした。
引き続き反応液を20℃で撹拌しつつ、メタノール100mlを添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、471gの(メタ)アクリル系トリブロック共重合体(A)(以下「(メタ)アクリル系トリブロック共重合体(A2)」と称する)を得た。
(工程(1))
内部を乾燥し、窒素置換した3Lのフラスコに、トルエン1.5Lを添加したのち、フラスコ内の溶液を攪拌しながら、ルイス塩基として1,1,4,7,10,10-ヘキサメチルトリエチレンテトラミン3.7ml(13.7mmol)、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液36.1ml(16.2mol)を順次添加したのち、-20℃に冷却した。これに有機リチウム化合物としてsec-ブチルリチウムの1.30mol/Lシクロヘキサン溶液10ml(13.0mmol)を加え、単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート18.7ml(78.0mmol)とメタクリル酸メチル4.1ml(39.0mmol)の混合物22.8mlを一括で添加し、アニオン重合を開始した。単量体の添加終了から280分後に重合反応液は当初の黄色から無色に変わった。さらに20分撹拌後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液15.9ml(7.2mol)を加え、その1分後に単量体としてアクリル酸n-ブチル501ml(3.48mol)を5ml/分の速度で添加した。アクリル酸n-ブチルを添加終了直後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート16.1ml(67.1mmol)とメタクリル酸メチル3.6ml(33.6mmol)との混合物19.7mlを一括で添加したのち、2℃/分の速度で10℃に昇温した。単量体の添加終了から300分後に反応液をサンプリングした。
引き続き反応液を20℃で撹拌しつつ、メタノール100mlを添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、487gの(メタ)アクリル系トリブロック共重合体(A)(以下「(メタ)アクリル系トリブロック共重合体(A3)」と称する)を得た。
(工程(1))
内部を乾燥し、窒素置換した3Lのフラスコに、トルエン1.5Lを添加したのち、フラスコ内の溶液を攪拌しながら、ルイス塩基として1,1,4,7,10,10-ヘキサメチルトリエチレンテトラミン7.4ml(27.3mmol)、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液63.6ml(28.6mol)を順次添加したのち、-20℃に冷却した。これに有機リチウム化合物としてsec-ブチルリチウムの1.30mol/Lシクロヘキサン溶液20ml(26.0mol)を加え、単量体としてメタクリル酸2-(トリメチルシリルオキシ)エチル17ml(78.0mmol)とメタクリル酸メチル16.6ml(156mmol)の混合物33.6mlを一括で添加し、アニオン重合を開始した。単量体の添加終了から80分後に、重合反応液は当初の黄色から無色に変わった。さらに20分撹拌後に反応液をサンプリングした。
引き続き反応液を-20℃で撹拌しつつ、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液を31.8ml(14.3mol)加え、その1分後に単量体としてアクリル酸n-ブチル504ml(3.5mol)を10ml/分の速度で添加した。得られた反応液を撹拌しつつ、単量体添加終了から1分後に、メタノールを100ml添加することにより、アニオン重合を停止させた。
得られた反応液にジクロロ酢酸22ml(267mmol)を添加し、室温で30分間攪拌した。次いで、得られた溶液を10Lのメタノール中に注ぎ、生成した重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、441gの重合体を回収した。
合成例2と同様に工程(1)、工程(2)を行ったのち、引き続き反応液を撹拌しつつ、-20℃でメタノールを100ml添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、449gの(メタ)アクリル系ジブロック共重合体(B)(以下「(メタ)アクリル系ジブロック共重合体(B2)」と称する)を得た。
合成例3と同様に工程(1)、工程(2)を行ったのち、引き続き反応液を撹拌しつつ-20℃でメタノールを100ml添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、431gの(メタ)アクリル系ジブロック共重合体(B)(以下「(メタ)アクリル系ジブロック共重合体(B3)」と称する)を得た。
(工程(1))
内部を乾燥し、窒素置換した3Lのフラスコに、トルエン1.5Lを添加したのち、フラスコ内の溶液を攪拌しながら、ルイス塩基として1,1,4,7,10,10-ヘキサメチルトリエチレンテトラミン7.4ml(27.3mmol)、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液63.6ml(28.6mmol)を順次添加したのち、-20℃に冷却した。これに有機リチウム化合物としてsec-ブチルリチウムの1.30mol/Lシクロヘキサン溶液20ml(26.0mmol)を加え、単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート18.7ml(78.0mmol)とメタクリル酸メチル16.6ml(156mmol)の混合物35.3mlを一括で添加し、アニオン重合を開始した。単量体の添加終了から80分後に重合反応液は当初の黄色から無色に変わった。さらに20分撹拌後に反応液をサンプリングした。
(工程(2))
引き続き反応液を-20℃で撹拌しつつ、有機アルミニウム化合物としてイソブチルビス(2,6-ジ-t-ブチル-4-メチルフェノキシ)アルミニウムの0.450mol/Lトルエン溶液を31.8ml(14.3mmol)加え、その1分後に単量体としてアクリル酸n-ブチル504ml(3.5mol)を10ml/分の速度で添加した。単量体の添加終了直後に、工程(2)の反応液をサンプリングした。
(工程(3))
引き続き反応液を-20℃でさらに20分撹拌した後に、単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート16.3ml(67.8mmol)とメタクリル酸メチル14.4ml(136mmol)の混合物30.7mlを一括で添加したのち、2℃/分の速度で20℃に昇温した。単量体の添加終了から60分後に反応液をサンプリングした。
(工程(4))
引き続き反応液を20℃で撹拌しつつ、メタノールを100ml添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、449gの重合体組成物(以下「重合体組成物(C1)」と称する)を得た。重合体組成物(C1)における部分構造(1)の含有量は3.7モル%であった。
工程(1)で単量体として1,1-ジメチルプロパン-1,3-ジオールジメタクリレート16.4ml(68.4mmol)とメタクリル酸メチル3.63ml(34.1mmol)の混合物20.0mlを添加し、工程(2)で単量体としてアクリル酸n-ブチル438ml(3.05mol)を5ml/分の速度で添加する以外は、合成例6と同様に工程(1)、工程(2)を行ったのち、引き続き反応液を撹拌しつつ-20℃でメタノールを100ml添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、372gの(メタ)アクリル系ジブロック共重合体(B)(以下「(メタ)アクリル系ジブロック共重合体(B4)」と称する)を得た。
工程(2)で単量体としてアクリル酸n-ブチル150ml(1.0mol)を10ml/分の速度で添加する以外は、合成例2と同様に工程(1)、工程(2)を行ったのち、引き続き反応液を撹拌しつつ、-20℃でメタノールを100ml添加することにより、アニオン重合を停止させた。得られた溶液を10Lのメタノール中に注ぎ、重合体を沈殿させ、濾過によって回収し、100℃、30Paで乾燥し、132gの(メタ)アクリル系ジブロック共重合体(B)(以下「(メタ)アクリル系ジブロック共重合体(B5)」と称する)を得た。
(メタ)アクリル系トリブロック共重合体(A)として合成例1で得られた(メタ)アクリル系トリブロック共重合体(A1)90質量部、および(メタ)アクリル系ジブロック共重合体(B)として合成例4で得られた(メタ)アクリル系ジブロック共重合体(B1)10質量部からなる重合体成分100質量部、光重合開始剤として1-ヒドロキシシクロヘキシルフェニルケトン2質量部、ならびに溶媒としてトルエン100質量部を混合して、溶液を作製した。得られた溶液から、20℃常圧で大部分のトルエンを除去した後に、さらに70℃、30Paの加温減圧下でトルエンを完全に除去し、活性エネルギー線硬化性組成物を得た。得られた活性エネルギー線硬化性組成物の粘度、硬化速度、硬化物の弾性率を下記の方法で評価した。評価結果を表2に示す。
活性エネルギー線硬化性組成物の粘度は、HAAKE製MARS IIIを用いて測定した。測定モードとして定常流粘度測定モードを使用し、φ35mm、1°傾斜コーンプレート上に活性エネルギー線硬化性組成物を設置し、測定温度25℃、測定ギャップ0.05mm、せん断速度1(1/s)の測定条件でη(Pa・s)を測定した。
活性エネルギー線硬化性組成物の硬化速度は、HAAKE製MARS IIIを用いて評価した。測定モードとして高速OSC時間依存性測定モードを使用し、φ20mmパラレルプレート上に活性エネルギー線硬化性組成物を厚さ50μmで塗工し、測定温度25℃、測定ギャップ0.15mm、測定周波数5Hzの条件で、UVランプ(Lumen Dynamics製Omni Cure series2000、照射強度150mW/cm2)を照射しながら粘弾性測定を行い、貯蔵せん断弾性率(G')と損失せん断弾性率(G'')がクロスオーバーする時間を測定し、硬化速度の指標とした。
活性エネルギー線硬化性組成物の柔軟性は、離型PETフィルム(K1504、東洋紡製)の四辺に1mm厚みのスペーサーを設置し、該PETフィルム上に活性エネルギー線硬化性組成物を流し込み、さらにその上にPETフィルムを気泡が入らないように載せた後、紫外線照射装置HTE-3000B INTEGRATOR814M(HI-TECH社製)を用いて、離型PETフィルム上に紫外線を5000mJ/cm2照射することで活性エネルギー線硬化性組成物を硬化させて作製したフィルムを用いて動的粘弾性測定装置(株式会社ユービーエム製「Rheogel E-4000」)を用いて、温度依存性(引っ張り)モード(周波数:11Hz)で、昇温速度を3℃/分、-100℃から180℃まで昇温して、貯蔵弾性率を測定し、25℃における貯蔵弾性率E'(Pa)を柔軟性の指標とした。
(メタ)アクリル系トリブロック共重合体(A)の種類および量、ならびに(メタ)アクリル系ジブロック共重合体(B)の種類および量を表2に記載されるとおりに変更する以外は、実施例1と同様に活性エネルギー線硬化性組成物を作製し、該活性エネルギー線硬化性組成物の粘度、硬化速度、硬化物の弾性率を評価した。評価結果を表2に示す。
重合体成分100質量部を重合体組成物(C1)100質量部に変更する以外は、実施例1と同様に活性エネルギー線硬化性組成物を作製し、該活性エネルギー線硬化性組成物の粘度、硬化速度、硬化物の弾性率を評価した。評価結果を表2に示す。
(メタ)アクリル系トリブロック共重合体(A)の種類および量、ならびに(メタ)アクリル系ジブロック共重合体(B)の種類および量を表3に記載されるとおりに変更する以外は、実施例1と同様に活性エネルギー線硬化性組成物を作製し、該活性エネルギー線硬化性組成物の粘度、硬化速度、硬化物の弾性率を評価した。評価結果を表3に示す。
重合体成分を、表3に記載の(メタ)アクリル系トリブロック共重合体(A)に変更する以外は、実施例1と同様に活性エネルギー線硬化性組成物を作製し、該活性エネルギー線硬化性組成物の粘度、硬化速度、硬化物の弾性率を評価した。評価結果を表3に示す。
(メタ)アクリル系トリブロック共重合体(A)の種類および量、ならびに(メタ)アクリル系ジブロック共重合体(B)の種類および量を表3に記載されるとおりに変更する以外は、実施例1と同様に活性エネルギー線硬化性組成物を作製し、該活性エネルギー線硬化性組成物の粘度、硬化速度、硬化物の弾性率を評価した。評価結果を表3に示す。
Claims (3)
- 下記一般式(1)で示される部分構造を含む活性エネルギー線硬化性基を有する(メタ)アクリル系重合体ブロック(aA)および活性エネルギー線硬化性基を有さない(メタ)アクリル系重合体ブロック(bA)を含有する(メタ)アクリル系トリブロック共重合体(A)と、下記一般式(1)で示される部分構造を含む活性エネルギー線硬化性基を有する(メタ)アクリル系重合体ブロック(aB)および活性エネルギー線硬化性基を有さない(メタ)アクリル系重合体ブロック(bB)を含有する(メタ)アクリル系ジブロック共重合体(B)とを含有し、かつ前記(メタ)アクリル系ジブロック共重合体(B)に含まれる(メタ)アクリル系重合体ブロック(bB)の数平均分子量Mn(bB)と前記(メタ)アクリル系トリブロック共重合体(A)に含まれる(メタ)アクリル系重合体ブロック(bA)1個あたりの数平均分子量Mn(bA)との比率Mn(bB)/Mn(bA)が0.2~2.0の範囲である活性エネルギー線硬化性組成物。
- さらに、光重合開始剤を含有してなる、請求項1に記載の活性エネルギー線硬化性組成物。
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CN201580044046.6A CN106574029A (zh) | 2014-08-19 | 2015-07-17 | 活性能量射线固化性组合物 |
KR1020177006933A KR20170043579A (ko) | 2014-08-19 | 2015-07-17 | 활성 에너지선 경화성 조성물 |
JP2016543870A JPWO2016027602A1 (ja) | 2014-08-19 | 2015-07-17 | 活性エネルギー線硬化性組成物 |
EP15834202.2A EP3184563A4 (en) | 2014-08-19 | 2015-07-17 | Active energy ray-curable composition |
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JP2017165807A (ja) * | 2016-03-14 | 2017-09-21 | アイカ工業株式会社 | テープ用光硬化性樹脂組成物 |
JP2017190463A (ja) * | 2017-07-21 | 2017-10-19 | 株式会社クラレ | 粘接着剤組成物 |
WO2018181251A1 (ja) * | 2017-03-31 | 2018-10-04 | 東亞合成株式会社 | 硬化性樹脂組成物及びその製造方法 |
JPWO2017110439A1 (ja) * | 2015-12-25 | 2018-10-11 | 株式会社クラレ | (メタ)アクリル系ブロック共重合体および該(メタ)アクリル系ブロック共重合体を含有する活性エネルギー線硬化性組成物 |
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JP7020472B2 (ja) * | 2017-02-23 | 2022-02-16 | 日本ゼオン株式会社 | 電子デバイス用樹脂フィルム及び電子デバイス |
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- 2015-07-17 CN CN201580044046.6A patent/CN106574029A/zh active Pending
- 2015-07-17 US US15/504,457 patent/US20170240739A1/en not_active Abandoned
- 2015-07-17 KR KR1020177006933A patent/KR20170043579A/ko unknown
- 2015-08-14 TW TW104126473A patent/TW201607983A/zh unknown
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JPWO2017110439A1 (ja) * | 2015-12-25 | 2018-10-11 | 株式会社クラレ | (メタ)アクリル系ブロック共重合体および該(メタ)アクリル系ブロック共重合体を含有する活性エネルギー線硬化性組成物 |
JP2017165807A (ja) * | 2016-03-14 | 2017-09-21 | アイカ工業株式会社 | テープ用光硬化性樹脂組成物 |
WO2018181251A1 (ja) * | 2017-03-31 | 2018-10-04 | 東亞合成株式会社 | 硬化性樹脂組成物及びその製造方法 |
JPWO2018181251A1 (ja) * | 2017-03-31 | 2020-02-06 | 東亞合成株式会社 | 硬化性樹脂組成物及びその製造方法 |
JP7081592B2 (ja) | 2017-03-31 | 2022-06-07 | 東亞合成株式会社 | 硬化性樹脂組成物及びその製造方法 |
JP2017190463A (ja) * | 2017-07-21 | 2017-10-19 | 株式会社クラレ | 粘接着剤組成物 |
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US20170240739A1 (en) | 2017-08-24 |
JPWO2016027602A1 (ja) | 2017-06-01 |
TW201607983A (zh) | 2016-03-01 |
EP3184563A4 (en) | 2018-01-17 |
CN106574029A (zh) | 2017-04-19 |
EP3184563A1 (en) | 2017-06-28 |
KR20170043579A (ko) | 2017-04-21 |
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