JP7153665B2 - (メタ)アクリル系ブロック共重合体およびそれを含有する活性エネルギー線硬化性組成物 - Google Patents
(メタ)アクリル系ブロック共重合体およびそれを含有する活性エネルギー線硬化性組成物 Download PDFInfo
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- JP7153665B2 JP7153665B2 JP2019554204A JP2019554204A JP7153665B2 JP 7153665 B2 JP7153665 B2 JP 7153665B2 JP 2019554204 A JP2019554204 A JP 2019554204A JP 2019554204 A JP2019554204 A JP 2019554204A JP 7153665 B2 JP7153665 B2 JP 7153665B2
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- meth
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- acrylate
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 84
- 229920001400 block copolymer Polymers 0.000 title claims description 79
- 239000000203 mixture Substances 0.000 title claims description 50
- 229920000642 polymer Polymers 0.000 claims description 60
- 239000000178 monomer Substances 0.000 claims description 49
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 42
- 230000036961 partial effect Effects 0.000 claims description 26
- 229920000058 polyacrylate Polymers 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- -1 2,2-dimethylbutyl group Chemical group 0.000 description 92
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 78
- 150000001875 compounds Chemical class 0.000 description 33
- 238000000034 method Methods 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 150000002430 hydrocarbons Chemical group 0.000 description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 16
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 238000010551 living anionic polymerization reaction Methods 0.000 description 14
- 239000002879 Lewis base Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 150000007527 lewis bases Chemical class 0.000 description 12
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 12
- 150000002900 organolithium compounds Chemical class 0.000 description 12
- 239000002243 precursor Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 239000004014 plasticizer Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 8
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 8
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- AHRHOJAODFDUBQ-UHFFFAOYSA-N 3-methylbut-3-enyl 2-methylprop-2-enoate Chemical compound CC(=C)CCOC(=O)C(C)=C AHRHOJAODFDUBQ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 125000005396 acrylic acid ester group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 150000003512 tertiary amines Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- HRVOCQZRIAABLU-UHFFFAOYSA-L bis(2,6-ditert-butyl-4-methylphenoxy)-(2-methylpropyl)alumane Chemical compound CC(C)(C)C=1C=C(C)C=C(C(C)(C)C)C=1O[Al](CC(C)C)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C HRVOCQZRIAABLU-UHFFFAOYSA-L 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 3
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 3
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical compound CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 2
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 2
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 2
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- IXPWKHNDQICVPZ-UHFFFAOYSA-N 2-methylhex-1-en-3-yne Chemical compound CCC#CC(C)=C IXPWKHNDQICVPZ-UHFFFAOYSA-N 0.000 description 2
- GHHGVSCQWPVENX-UHFFFAOYSA-N 2-methylpent-1-en-3-one Chemical compound CCC(=O)C(C)=C GHHGVSCQWPVENX-UHFFFAOYSA-N 0.000 description 2
- WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 2
- RQWCMLILJZDGQG-UHFFFAOYSA-N 2-trimethylsilyloxyethyl prop-2-enoate Chemical compound C[Si](C)(C)OCCOC(=O)C=C RQWCMLILJZDGQG-UHFFFAOYSA-N 0.000 description 2
- DCEGHEFYVNDALO-UHFFFAOYSA-N 3,3,3-trifluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)F DCEGHEFYVNDALO-UHFFFAOYSA-N 0.000 description 2
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZESXUEKAXSBANL-UHFFFAOYSA-N trifluoromethyl prop-2-enoate Chemical compound FC(F)(F)OC(=O)C=C ZESXUEKAXSBANL-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- 229940036248 turpentine Drugs 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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- 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
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- 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
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- 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
-
- 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
- C08F287/00—Macromolecular compounds obtained by polymerising monomers on to block polymers
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- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
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- 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
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- 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
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
[1]下記一般式(1)で示される部分構造(1)を含む活性エネルギー線硬化性基を有するメタクリル系重合体ブロック(A)と、活性エネルギー線硬化性基を有さないアクリル系重合体ブロック(B)とを含有する、(メタ)アクリル系ブロック共重合体;
[2]前記メタクリル系重合体ブロック(A)を構成する全単量体単位のモル数に対する前記部分構造(1)のモル数の占める割合が0.1~50モル%である、上記[1]の(メタ)アクリル系ブロック共重合体;
[3]上記[1]または[2]の(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;
に関する。
なお、本明細書において「(メタ)アクリル」とは「メタクリル」と「アクリル」との総称を意味する。
メタクリル系重合体ブロック(A)は下記一般式(1)で示される部分構造(1)を含む活性エネルギー線硬化性基を有する。
また、メタクリル系重合体ブロック(A)の全単量体単位のモル数に対する、1個のメタクリロイル基を有する単官能メタクリル酸エステル(例えば、メタクリル酸メチル)に由来する単量体単位のモル数の占める割合は、50モル%以上99.9モル%以下の範囲内であることが好ましく、60モル%以上99.5モル%以下の範囲内であることがより好ましい。
なお、本明細書において数平均分子量および後述する重量平均分子量はゲルパーミエーションクロマトグラフィー(GPC)法(標準ポリスチレン換算)により測定される値である。
(メタ)アクリル系ブロック共重合体は、活性エネルギー線硬化性基を有さないアクリル系重合体ブロック(B)を含有する。
本発明の(メタ)アクリル系ブロック共重合体の数平均分子量(Mn)は、特に制限されないが、取り扱い性、粘度、力学特性等の観点から、4,000以上400,000以下であることが好ましく、7,000以上200,000以下であることがより好ましく、10,000以上100,000以下であることがさらに好ましい。本発明の(メタ)アクリル系ブロック共重合体の分子量分布(Mw/Mn)、すなわち重量平均分子量(Mw)/数平均分子量(Mn)は2.00以下が好ましく、1.01以上2.00以下の範囲内であることがより好ましく、1.01以上1.80以下の範囲内であることがさらに好ましく、1.01以上1.50以下の範囲内であることが最も好ましい。
AlR2(R3)(R4) (A-1)
上記一般式(A-1)中、R2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、R3およびR4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R3およびR4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。
AlR5(R6)(R7) (A-2)
上記一般式(A-2)中、R5はアリールオキシ基を表し、R6およびR7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。
本発明の(メタ)アクリル系ブロック共重合体は、活性エネルギー線硬化性組成物の材料として好ましく用いることができる。
下記の実施例および比較例における重合後の各単量体の消費率は、反応液0.5mLを採取してメタノール0.5mL中に入れて混合後、該混合液から0.1mLを採取して、重クロロホルム0.5mLに溶解させて1H-NMR測定を下記の測定条件にて行い、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5.79~6.37ppm)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℃
下記の実施例および比較例において、得られた重合体のGPC測定を下記の測定条件にて行い、標準ポリスチレン換算の数平均分子量(Mn)および重量平均分子量(Mw)の値を求め、これらの値から分子量分布(Mw/Mn)の値を算出した。
(GPC測定条件)
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
溶離液流量:0.35mL/分
カラム温度:40℃
検出方法:示差屈折率(RI)
下記の実施例および比較例で得られた活性エネルギー線硬化性組成物の硬化速度は、粘度・粘弾性測定装置(HAAKE製、MARS III)を用いて評価した。
φ20mmのパラレルプレート上に、上記実施例および比較例で得られた活性エネルギー線硬化性組成物を1g滴下し、塗膜を形成した。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、測定温度25℃、測定ギャップ0.30mm、測定周波数1Hzの条件で、UVランプ(Lumen Dynamics製、Omni Cure series2000、照射強度50mW/cm2)を用いて紫外光を照射しながら粘弾性測定を実施した。
紫外光照射開始時の貯蔵せん断弾性率(Pa)をG’(0)、紫外光照射開始から20秒後(1000mJ/cm2照射後)の貯蔵せん断弾性率(Pa)をG’(20)、紫外光照射開始から120秒後(6000mJ/cm2照射後)に飽和値に達した貯蔵せん断弾性率(Pa)をG’(120)とし、以下の式にしたがって得られる反応率(%)を硬化速度の指標とした。
反応率(%)={G’(20)-G’(0)}/{G’(120)-G’(0)}×100
(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1.30kgを添加したのち、フラスコ内の溶液を撹拌しながら、さらに、ルイス塩基としてN,N,N',N”,N”-ペンタメチルジエチレントリアミン1.5gおよび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)アルミニウムを26質量%含むトルエン溶液20gを順次添加したのち、-30℃に冷却した。これに有機リチウム化合物としてsec-ブチルリチウムを10質量%含むシクロヘキサン溶液3.7gを加え、その後、単量体としてBMA3.0gとMMA3.9gとの混合物6.9gを一括で添加し、アニオン重合を開始した。引き続き、反応液を-30℃で12時間撹拌して反応液をサンプリングした。
工程(1)におけるBMA、およびMMAの消費率は100%であった。
引き続き反応液を-30℃で撹拌しつつ、単量体として2-EHA445gを5g/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。
工程(2)における2-EHAの消費率は100%であった。
引き続き反応液を-30℃で撹拌しつつ、単量体としてBMA2.6gとMMA3.4gとの混合物6.0gを一括で添加した後、25℃に昇温した。上記混合物の添加から300分後に反応液をサンプリングした。
工程(3)におけるBMA、およびMMAの消費率は100%であった。
引き続き反応液を25℃で撹拌しつつ、メタノールを40g加えることによりアニオン重合を停止させて、メタクリル系重合体ブロック(A)-アクリル系重合体ブロック(B)-メタクリル系重合体ブロック(A)の(A-B-A)の順に結合したトリブロック共重合体である(メタ)アクリル系ブロック共重合体を含有する溶液を得た。かかる溶液からサンプリングした(メタ)アクリル系ブロック共重合体のMnは71,000、Mw/Mnは1.03であった。
次いで得られた溶液を5,000gのメタノール中に注ぎ、油状沈殿物を析出させた。油状沈殿物を回収後、乾燥させることにより、420gの(メタ)アクリル系ブロック共重合体(以下、「(メタ)アクリル系ブロック共重合体<1>」と称する)を得た。
次いで、(メタ)アクリル系ブロック共重合体<1>80gに対して、反応性希釈剤としてアクリル酸n-オクチルを20gと光重合開始剤として1-ヒドロキシシクロヘキシルフェニルケトン(チバ・スペシャルティ・ケミカルズ製、イルガキュア(登録商標)184)を5g添加し、撹拌、溶解させて、105gの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硬化速度を前述する方法で測定したところ、反応率は94.0%であった。結果を表2に示す。
工程(1)~(3)でのBMA、MMA、2-EHA、BAの使用量を表1のように変更したこと以外は、実施例1と同じ方法によって、(メタ)アクリル系ブロック共重合体を得た。なお、得られた(メタ)アクリル系ブロック共重合体は、(メタ)アクリル系ブロック共重合体<2>と称する。
さらに、工程(6)でのアクリル酸n-オクチル、1-ヒドロキシシクロヘキシルフェニルケトンの使用量を表2のように変更したこと以外は、実施例1と同様の方法によって、(メタ)アクリル系ブロック共重合体<2>を含有する各活性エネルギー線硬化性組成物を得た。
工程(1)~(3)でのBMA、AMA、MMA、2-EHA、BAの使用量を表1のように変更したこと以外は、実施例1と同じ方法によって、(メタ)アクリル系ブロック共重合体を得た。なお、比較例1および2で得られた(メタ)アクリル系ブロック共重合体は、それぞれ(メタ)アクリル系ブロック共重合体<3>または<4>と称する。
さらに、工程(6)でのアクリル酸n-オクチル、1-ヒドロキシシクロヘキシルフェニルケトンの使用量を表2のように変更したこと以外は、実施例1と同様の方法によって、(メタ)アクリル系ブロック共重合体<3>または<4>を含有する各活性エネルギー線硬化性組成物を得た。
一方、メタクリル系重合体ブロック(A)に部分構造(1)を含む活性エネルギー線硬化性基を持つ単量体単位を含有しない比較例1および2の活性エネルギー線硬化性組成物は硬化速度が遅い。これは、活性エネルギー線硬化性基であるアリル基がα位に電子供与性を示す炭化水素基を持たず、活性エネルギー線硬化性基の反応性が低いためと推察される。
Claims (3)
- 前記メタクリル系重合体ブロック(A)を構成する全単量体単位のモル数に対する前記部分構造(1)のモル数の占める割合が0.1~50モル%である、請求項1に記載の(メタ)アクリル系ブロック共重合体。
- 請求項1または2に記載の(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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