JP6277381B2 - グリシジル基含有(メタ)アクリルアミド - Google Patents
グリシジル基含有(メタ)アクリルアミド Download PDFInfo
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- JP6277381B2 JP6277381B2 JP2016510320A JP2016510320A JP6277381B2 JP 6277381 B2 JP6277381 B2 JP 6277381B2 JP 2016510320 A JP2016510320 A JP 2016510320A JP 2016510320 A JP2016510320 A JP 2016510320A JP 6277381 B2 JP6277381 B2 JP 6277381B2
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- Prior art keywords
- meth
- acrylamide
- group
- reaction
- methyl
- Prior art date
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims description 107
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 title claims description 48
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 38
- -1 alicyclic hydrocarbon Chemical class 0.000 claims description 30
- 239000011342 resin composition Substances 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
- 125000005011 alkyl ether group Chemical group 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 description 62
- 238000000034 method Methods 0.000 description 48
- 150000002848 norbornenes Chemical class 0.000 description 47
- 239000000178 monomer Substances 0.000 description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 40
- 239000002904 solvent Substances 0.000 description 33
- 238000011156 evaluation Methods 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- 239000003054 catalyst Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 22
- 238000004821 distillation Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- 239000003513 alkali Substances 0.000 description 14
- 150000001414 amino alcohols Chemical class 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 238000001723 curing Methods 0.000 description 13
- 239000003444 phase transfer catalyst Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 238000007112 amidation reaction Methods 0.000 description 10
- 125000004185 ester group Chemical group 0.000 description 10
- 238000007142 ring opening reaction Methods 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000000197 pyrolysis Methods 0.000 description 9
- 238000007086 side reaction Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- 206010070835 Skin sensitisation Diseases 0.000 description 8
- 238000007259 addition reaction Methods 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 150000003944 halohydrins Chemical class 0.000 description 8
- 231100000370 skin sensitisation Toxicity 0.000 description 8
- 206010040880 Skin irritation Diseases 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000036556 skin irritation Effects 0.000 description 7
- 231100000475 skin irritation Toxicity 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 5
- PFXXTYUSZRFQHC-UHFFFAOYSA-N 2-methylhept-5-enamide Chemical compound CC=CCCC(C)C(N)=O PFXXTYUSZRFQHC-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XGIKILRODBEJIL-UHFFFAOYSA-N 1-(ethylamino)ethanol Chemical compound CCNC(C)O XGIKILRODBEJIL-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- USWANRSZMQLWTG-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)butyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOCC1CO1 USWANRSZMQLWTG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010835 comparative analysis Methods 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 description 3
- VYHUMZYFJVMWRC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methylprop-2-enamide Chemical compound OCCN(C)C(=O)C=C VYHUMZYFJVMWRC-UHFFFAOYSA-N 0.000 description 3
- SOBKSPRFLXNMAI-UHFFFAOYSA-N n-(2-hydroxyethyl)bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)NCCO)CC1C=C2 SOBKSPRFLXNMAI-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- RJBIZCOYFBKBIM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]propane Chemical compound COCCOCCOC(C)C RJBIZCOYFBKBIM-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 101000720524 Gordonia sp. (strain TY-5) Acetone monooxygenase (methyl acetate-forming) Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- NNTWPKJOSYALGA-UHFFFAOYSA-N N-(2-hydroxyethyl)-N-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1C2C(C(=O)N(CCO)C)CC1C=C2 NNTWPKJOSYALGA-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- HYLXOKYELSZAQQ-UHFFFAOYSA-N N-ethyl-N-(2-hydroxyethyl)bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1C2C(C(=O)N(CCO)CC)CC1C=C2 HYLXOKYELSZAQQ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
Description
(1)一般式(1)(式中、R1はHまたはCH3を、R2はHまたは炭素原子数1〜8のアルキル基、アルキルエーテル基、脂環式炭化水素、芳香族炭化水素を示し、直鎖のみならず分岐構造も表し、R3は炭素原子数1〜12のアルキレン基、アルキレンエーテル基、脂環式炭化水素、芳香族炭化水素を示し、直鎖のみならず分岐構造も表す。)で表されるグリシジル基含有(メタ)アクリルアミド、
(3)一般式(2)(式中、R1はHまたはCH3を、R2はHまたは炭素原子数1〜8のアルキル基、アルキルエーテル基、脂環式炭化水素、芳香族炭化水素を示し、直鎖のみならず分岐構造も表し、R3は炭素原子数1〜12のアルキレン基、アルキレンエーテル基、脂環式炭化水素、芳香族炭化水素を示し、直鎖のみならず分岐構造も表す。)で表されるグリシジル基含有ノルボルネン誘導体を熱分解することで前記(1)または(2)に記載のグリシジル基含有(メタ)アクリルアミドを得ることを特徴とする製造方法、
(7)相間移動触媒が、4級アンモニウム塩、ホスホニウム塩、ピリジニウム塩、クラウンエーテル、ポリオキシアルキレングリコールまたはそのアルキルエーテルからなる群から選ばれる一種、あるいは二種以上の混合物である前記(6)に記載のグリシジル基含有(メタ)アクリルアミドの製造方法、
(8)前記(1)または(2)に記載のグリシジル基含有(メタ)アクリルアミドを用いた活性エネルギー線硬化性樹脂組成物
を提供するものである。
本発明の新規なグリシジル基含有(メタ)アクリルアミドは、一般式(1)で表される。
還流冷却管、撹拌機、温度計を設けた5000mL容量のフラスコに、ビシクロ[2.2.1]ヘプタ−5−エン−2−カルボン酸メチル(略称ESD)2000g、アミノエタノール1200g、ナトリウムメトキシド25%メタノール溶液14.2gを加え、100℃まで昇温し、3時間反応させた。反応終了後、96%の硫酸3.4gで中和し、減圧下で副生したメタノール、水及び未反応の原料などを留出除去し、N−ヒドロキシエチル−ビシクロ[2.2.1]ヘプト−5−エン−2−カルボキサミド(略称HEAD)2380gを淡黄色液体として得た。ガスクロマトグラフで分析した結果、純度は99.8%であった。
得られたHEADにエピクロロヒドリン500gを加えて20℃に調整し、三フッ化ホウ素ジエチルエーテル11.4gを加えた後、さらにエピクロロヒドリン1320gを2時間かけて滴下した。滴下後、さらに1時間残反応を実施した。この反応液に、48%水酸化ナトリウム水溶液1300gを2時間かけて滴下した後、1時間残反応を実施した。得られた反応液から析出塩を濾別した後、濾液を少量の水で洗浄した。さらに有機層に含まれる低沸点成分を減圧下で留出除去し、N−ヒドロキシエチル−ビシクロ[2.2.1]ヘプト−5−エン−2−カルボキサミドグリシジルエーテル(略称HEADGE)1683gを得た。純度は84.7%であった。
得られたHEADGEにハイドロキノンモノメチルエーテル(略称MHQ)1gを加え、30Torrの減圧下、420℃に加熱した熱分解管へ連続供給しながら気相熱分解させ、生成したN−ヒドロキシエチルアクリルアミドグリシジルエーテル(略称HEAAGE)を30℃の熱交換器で凝縮し、粗モノマーとして1051gを取得した。この粗モノマーを充填塔付きの蒸留精製装置に移し、フェノチアジン(TDA)1.1gを加え、減圧蒸留により精製を行い、淡黄色液体として純度93.9%のHEAAGE(約140℃/0.5Torr)を717g取得した。
合成実施例1と同様にして得られたHEAD 1300gにエピクロロヒドリン1990gを加えて40℃に調整し、48%水酸化ナトリウム水溶液1200gを2時間かけて滴下した後、2時間残反応を実施した。得られた反応液を合成実施例1と同様に処理し、HEADGE 1119gを得た。純度は87.3%であった。
得られたHEADGEにMHQ 0.7gを加え、合成実施例1と同様にして気相熱分解させ、粗モノマーとして710gを取得した。この粗モノマーを充填塔付きの蒸留精製装置に移し、TDA 0.7gを加え、減圧蒸留により精製を行い、淡黄色液体として純度96.6%のHEAAGEを526g取得した。
合成実施例1と同様の反応容器に、N−メチル−アミノエタノール2500g、ナトリウムメトキシド25%メタノール溶液9.7gを加え、100℃まで昇温し、ESD1000gを2時間かけて滴下した。滴下終了後、残反応を2時間実施した。反応終了後、96%の硫酸2.3gで中和し、減圧下で副生したメタノール、水及び未反応の原料などを留出除去し、N−メチル−N−ヒドロキシエチル−ビシクロ[2.2.1]ヘプト−5−エン−2−カルボキサミド(略称MHEAD)1254gを淡黄色液体として得た。ガスクロマトグラフで分析した結果、純度は98.8%であった。
得られたMHEADにエピクロロヒドリン1780gを加えて40℃に調整し、48%水酸化ナトリウム水溶液1600gを2時間かけて滴下した後、5時間残反応を実施した。得られた反応液を合成実施例1と同様に処理し、N−メチル−N−ヒドロキシエチル−ビシクロ[2.2.1]ヘプト−5−エン−2−カルボキサミドグリシジルエーテル(略称MHADGE)1241gを得た。純度は88.6%であった。
得られたMHADGEにMHQ 0.8gを加え、合成実施例1と同様にして気相熱分解させ、N−メチル−N−ヒドロキシエチルアクリルアミドグリシジルエーテル(略称MHAGE)の粗モノマーとして795gを取得した。この粗モノマーを充填塔付きの蒸留精製装置に移し、アントラキノン(略称AQ)0.8gを加え、減圧蒸留により精製を行い、淡黄色液体として純度97.2%のMHAGE(約130℃/0.5Torr)を572g取得した。
合成実施例1と同様の反応容器に、N−エチル−アミノエタノール2600g、ナトリウムメトキシド25%メタノール溶液11.0gを加え、100℃まで昇温し、ESD900gを2時間かけて滴下した。滴下終了後、残反応を2時間実施した。反応終了後、96%の硫酸2.6gで中和し、減圧下で副生したメタノール、水及び未反応の原料などを留出除去し、N−エチル−N−ヒドロキシエチル−ビシクロ[2.2.1]ヘプト−5−エン−2−カルボキサミド(略称EHEAD)1230gを淡黄色液体として得た。ガスクロマトグラフで分析した結果、純度は95.7%であった。
得られたEHEADにエピクロロヒドリン1630gを加えて40℃に調整し、48%水酸化ナトリウム水溶液1470gを2時間かけて滴下した後、5時間残反応を実施した。得られた反応液を合成実施例1と同様に処理し、N−エチル−N−ヒドロキシエチル−ビシクロ[2.2.1]ヘプト−5−エン−2−カルボキサミドグリシジルエーテル(略称EHADGE)1523gを得た。純度は89.3%であった。
得られたEHADGEにMHQ 1.0gを加え、合成実施例1と同様にして気相熱分解させ、N−エチル−N−ヒドロキシエチルアクリルアミドグリシジルエーテル(略称EHAGE)の粗モノマーを974g取得した。この粗モノマーを充填塔付きの蒸留精製装置に移し、AQ 1.0gを加え、減圧蒸留により精製を行い、淡黄色液体として純度97.6%のEHAGE(約140℃/0.5Torr)を666g取得した。
合成実施例3と同様にして得られたMHEAD1250gにエピクロロヒドリン1780g、ベンジルトリエチルアンモニウムクロライド44gを加えて40℃に調整し、48%水酸化ナトリウム水溶液1600gを2.5時間かけて滴下した後、1時間残反応を実施した。得られた反応液から析出塩を濾別した後、濾液を少量の水で洗浄した。さらに有機層に含まれる低沸点成分を減圧下で留出除去し、MHADGE1436gを得た。純度は97.0%であった。
得られたMHADGEにジメトキシベンゼン(DMB)1.0gを加え、合成実施例1と同様にして気相熱分解させ、MHAGEの粗モノマーとして950gを取得した。この粗モノマーを充填塔付きの蒸留精製装置に移し、TDA 1.9gを加え、減圧蒸留により精製を行い、淡黄色液体として純度99.1%のMHAGEを774g取得した。
合成実施例1と同様の反応容器に、N−メチル−アミノエタノール900g、ナトリウムメトキシド25%メタノール溶液6.0g、TDA2.4gを加え、室温でメタクリル酸メチル800gを2時間かけて滴下し、さらに4時間反応させた。反応終了後、96%硫酸1.4gを加え、減圧下で副生したメタノール、未反応の原料などを留出除去し、N−メチル−N−ヒドロキシエチルメタクリルアミド(略称MHEMAA)1204gを黄色液体として得た。ガスクロマトグラフで分析した結果、純度は81.7%であった。
得られたMHEMAAに、エピクロロヒドリン2540gを加えて40℃に調整し、48%水酸化ナトリウム水溶液1150gを2時間かけて滴下した後、3時間残反応を実施した。得られた反応液から析出塩を濾別した後、濾液を少量の水で洗浄した。さらに有機層を充填塔付きの蒸留精製装置に移し、2,2,6,6−テトラメチルピペリジン1−オキシルフリーラジカル(TEMPO)0.3g、ジエトキシナフタレン(DEN)1.1gを加え、減圧蒸留により精製を行い、淡黄色液体として純度96.3%のN−メチル−N−ヒドロキシエチルメタクリルアミドグリシジルエーテル(略称MHMAGE)(約125℃/0.5Torr)を423g取得した。
合成実施例3と同様にして得られたMHEAD1250gにAQ2.4gを加え、合成実施例1と同様にして気相熱分解させ、N−メチル−N−ヒドロキシエチルアクリルアミド(略称MHEAA)の粗モノマーとして711gを取得した。
得られたMHEAA粗モノマーに、エピクロロヒドリン2550g、ポリエチレングリコールモノオレイルエーテル(n=2)600g、トリn−オクチルメチルアンモニウムクロライド67g、DMB 2.1gを加えて40℃に調整し、水酸化カリウム930gを2時間かけて徐々に加えた後、4時間残反応を実施した。得られた反応液から析出塩を濾別した後、濾液を少量の水で洗浄した。さらに有機層を充填塔付きの蒸留精製装置に移し、TDA 1.1gを加え、減圧蒸留により精製を行い、淡黄色液体として純度97.8%のMHAGEを359g取得した。
MHAGE:N−メチル−N−ヒドロキシエチルアクリルアミドグリシジルエーテル
GA:グリシジルアクリレート
GMA:グリシジルメタクリレート
4HBAGE:4−ヒドロキシブチルアクリレートグリシジルエーテル
DPHA:ジペンタエリスリトールヘキサアクリレート
PETA:ペンタエリスリトールトリアクリレート
UV−7600B:ポリウレタンアクリレート(日本合成化学工業社製)
「DMAA」:N,N−ジメチルアクリルアミド(KJケミカルズ社製、商品名「DMAA」)
「DEAA」:N,N−ジエチルアクリルアミド(KJケミカルズ社製、商品名「DEAA」)
「ACMO」:アクリロイルモルホリン(KJケミカルズ社製、商品名「ACMO」)
THFA:テトラヒドロフルフリルアクリレート
IBOA:イソボルニルアクリレート
AAc:アクリル酸
MEK:メチルエチルケトン
合成実施例3で得られたMHAGE 10gに光ラジカル重合開始剤としてBASF社製 商品名Darocur1173 0.3gを添加、混合し、紫外線(UV)硬化速度をリアルタイムFT−IR(測定機:Nicolet6700、検出器:MCT−A、UV照度:500mW/cm2)により測定した。紫外線硬化速度は800cm−1付近に現れるビニル基由来のCH面外変角振動バントの減少率が90%に到達するまでの紫外線照射時間で測定し、結果を表1に示す。なお、照射時間が短い程、硬化速度が速く、硬化性が良い。
評価実施例A−1のMHAGEの代わりに、GA(評価比較例A−2)、GMA(評価比較例A−3)、4HBAGE(評価比較例A−4)10gを用い、光ラジカル重合開始剤Darocur1173 0.3gを添加、混合し、評価実施例A−1と同様に評価した。結果を表1に示す。
合成例3で合成したMHAGE 40g、DPHA 40g、UV−7600B 20gを混合し、該混合液に対して光重合開始剤Darocur1173 3gを加え、混合溶解させ、紫外線硬化可能なハードコート剤を得た。その後、得られたハードコート剤を用いて、下記方法により紫外線硬化型ハードコート層を作製した。
厚さ100μmのポリエチレンテレフタラート(PET)フィルムを額縁状の木枠に固定し、フィルムを台座の上に押し当てた状態で、フィルムの先方の端にハードコート剤を帯状に滴下して、バーコーター(RDS 3)で全体に均等な力がかかるように両端を押さえ、回転させずに同じ速さ(5cm/sec)で手前まで引いて塗布し、塗膜を得た。次に塗布面を上向きにして紫外線照射を行って硬化させ、ハードコート層を得た。
紫外線硬化条件は、出力300W、単位当たり出力50W/cmの高圧水銀灯1本を設置した紫外線照射装置(オーク製作所社製 モデルOHD320M)を使用し、紫外線照度は20mW/cm2になるように試料板とランプの距離を調節した。塗膜の表面がベタつかなくなるまでに必要な照射時間を硬化時間として測定した。
(耐擦傷性試験)
#0000のスチールウールを用いて、200g/cm2の荷重をかけながら10往復させ、傷の発生の有無を評価した(◎:膜の剥離や傷の発生がほとんど認められない;○:膜にわずかな細い傷が認められる;△:膜全面に筋状の傷が認められる。;×:膜の剥離が生じる)。
(鉛筆硬度の評価)
JIS K 5400 8.4 手かき法(1990年版)に基づき評価した。
(密着性の評価)
JIS K 5400 8.5 碁盤目テープ法(1990年版)に基づき1mm角のます目を100個作成し、セロハンテープを貼り付け、一気に剥がした時に基材側にハードコート層が残ったます目の数を数えて評価した。
表2に記載の組成に変えた以外は評価実施例B−1と同様にハードコート層を作製、評価した。結果を表2に示す。
攪拌機、還流冷却管、温度計及びガス導入管を設けた500mL容量のセパラブルフラスコに、IBOA 50g、AAc 35g、MEK 250mLを投入し、撹拌下、窒素ガスで1時間脱気した。この後、2,2'−アゾビス(2,4−ジメチルバレロニトリル)(和光純薬工業株式会社製V−65)1.8gをMEK 30mLに溶解させた溶液を加え、70℃に昇温して6時間重合反応を実施することでプレポリマーを合成した。このプレポリマー液からMEKを蒸留除去し、プレポリマー濃度が70%になる様に調整した。導入ガスを窒素から空気に変更し、MHAGE 267g、MHQ 0.3g、トリフェニルホスフィン(TPP)1.3gを投入し、80℃のまま5時間反応させた。反応液を室温に戻し、側鎖にビニル基を有するアクリルポリマーとMHAGEの混合物の溶液(略称ポリマー液)を得た。該ポリマー液40g(固形分重量)にPETA 40g、DMAA 20g、光重合開始剤Darocur1173 3gを加え、混合溶解させ、ハードコート剤を得た。得られたハードコート剤を用いて、評価実施例B−1同様にPETフィルム上に塗布し、熱風乾燥機で120℃、3分の条件でMEKを除去した。その後、評価実施例B−1同様に紫外線照射を行って硬化させ、ハードコート層を得た。ハードコート層の特性を上記方法で評価し、結果を表3に示す。
表3に記載の組成に変えた以外は実施例C−1と同様にポリマー液を合成した後、ハードコート層を作製、評価した。結果を表3に示す。
合成例2で合成したMHAGEの皮膚刺激性試験、皮膚感作性試験、臭気判定試験結果を表4に示す。各試験方法は、下記の通りである。
(皮膚刺激性試験)
OECDガイドライン404(2002)に準拠して皮膚一次刺激性試験を行い、一次刺激性インデックス(P.I.I.)の値により比較評価した。数値が小さいほど皮膚一次刺激性が低い。
(皮膚感作性試験)
OECDガイドライン442B LLNA:BrdU−ELISA(2010)に準拠して皮膚感作性試験を行い、感作性インデックス(SI)が2になる濃度(EC2)により比較評価した。数値が大きいほど皮膚感作性が低い。
(臭気判定試験)
モノマーそのものの臭いを直接嗅いで比較評価した。
評価実施例D−1のMHAGEの代わりに、GA(評価比較例D−2)、GMA(評価比較例D−3)、4HBAGE(評価比較例D−4)を用い、評価実施例D−1と同様に評価した。結果を表4に示す。
Claims (3)
- 一般式(1)(式中、R1はHまたはCH3を、R 2 は炭素原子数1〜8のアルキル基、アルキルエーテル基、脂環式炭化水素、芳香族炭化水素を示し、直鎖のみならず分岐構造も表し、R3は炭素原子数1〜12のアルキレン基、アルキレンエーテル基、脂環式炭化水素、芳香族炭化水素を示し、直鎖のみならず分岐構造も表す。)で表されるグリシジル基含有(メタ)アクリルアミド。
- N−メチル−N−2−ヒドロキシエチル(メタ)アクリルアミドグリシジルエーテル、N−エチル−N−2−ヒドロキシエチル(メタ)アクリルアミドグリシジルエーテルであることを特徴とする請求項1に記載のグリシジル基含有(メタ)アクリルアミド。
- 請求項1または請求項2に記載のグリシジル基含有(メタ)アクリルアミドを用いたハードコート用活性エネルギー線硬化性樹脂組成物。
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