CN104583242A - Curable film-forming composition - Google Patents
Curable film-forming composition Download PDFInfo
- Publication number
- CN104583242A CN104583242A CN201380045312.8A CN201380045312A CN104583242A CN 104583242 A CN104583242 A CN 104583242A CN 201380045312 A CN201380045312 A CN 201380045312A CN 104583242 A CN104583242 A CN 104583242A
- Authority
- CN
- China
- Prior art keywords
- composition
- cured film
- formula
- repeating unit
- ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 113
- -1 acrylate compound Chemical class 0.000 claims abstract description 43
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 49
- 239000000126 substance Substances 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000010408 film Substances 0.000 description 85
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 40
- 230000006978 adaptation Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 239000000178 monomer Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- 239000011259 mixed solution Substances 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 208000037656 Respiratory Sounds Diseases 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- PMZBHPUNQNKBOA-UHFFFAOYSA-N 5-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C(O)=O)=CC(C(O)=O)=C1 PMZBHPUNQNKBOA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-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
- 150000001241 acetals Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-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
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
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- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
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- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 2
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- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 230000007774 longterm Effects 0.000 description 2
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- MMVJBWFKSYKXIA-UHFFFAOYSA-N ethoxyethane;2-methylprop-2-enoic acid Chemical compound CCOCC.CC(=C)C(O)=O MMVJBWFKSYKXIA-UHFFFAOYSA-N 0.000 description 1
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- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 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
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
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- 238000004321 preservation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 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
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 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
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 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 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
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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
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
- C08F299/065—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes from polyurethanes with side or terminal unsaturations
-
- 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
- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/02—Homopolymers or copolymers of esters
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- 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
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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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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Abstract
Provided is a curable film-forming composition containing (A) (A-1) a polymer having repeating units represented by formula (1), (B) a polyfunctional acrylate compound, (C) a radical polymerization initiator, and (D) a solvent. (In the formula, R1 represents a hydrogen atom, a methyl group, a chloro group, or a phenyl group. R2 represents a C1-5 alkyl group. L represents a C1-9 alkylene group.)
Description
Technical field
The present invention relates to the composition forming cured film.
Background technology
Now, due to the requirement in transport, preservation, replace glass substrate, the utilization of film substrate is in continuous increase.Film substrate forms web-like etc. when preserving and is saved, but, now, due to curved substrate, therefore for the material be coated with on film substrate, also require the flexibility same with film.
In addition, the films such as ito film define in the substrate of electrode, when tackiness agent being used for the laminating of substrate, due to the moisture of tackiness agent, produce the problems such as the deterioration of silver-colored distribution, short circuit, therefore need the top layer material by electrode and distribution protection.
On the other hand, top layer material is in the past for the purpose of coating on the glass substrate, in order to improve hardness containing inorganic particles (patent documentation 1).Such as, but for containing the method in the past such as inorganic particles, although hardness improves, without flexibility, produce and occur the unfavorable situations such as crackle when bending, therefore present situation to be applied to the coating to film substrate.
Prior art document
Patent documentation
Patent documentation 1: JP 2012-116975 publication
Summary of the invention
The problem that invention will solve
The present invention completes in view of the above problems, and object is to provide the composition of formation cured film of top layer material that can be used as having high-transmission rate, high adhesion, high rigidity, high flexibility and long-term reliability for ito film.
For solving the means of problem
The present inventor is in order to solve above-mentioned problem, repeatedly further investigate, found that: utilize the composition containing the polymkeric substance with specific repeating unit, polyfunctional acrylic ester compound, optional ion-trapping agent and optional multi-functional thiol's compound, the film that can solve above-mentioned problem can be obtained, complete the present invention.
That is, the invention provides:
1. form the composition of cured film, it is characterized in that, contain:
(A) (A-1) has the polymkeric substance of the repeating unit represented by following formula (1),
[changing 1]
(in formula, R
1represent hydrogen atom, methyl, chloro or phenyl.R
2represent the alkyl of carbonatoms 1 ~ 5.L represents the alkylidene group of carbonatoms 1 ~ 9.)
(B) polyfunctional acrylic ester compound,
(C) radical polymerization initiator, and
(D) solvent;
The composition of the formation cured film described in 2.1, wherein, as (A) composition, also has the polymkeric substance of the repeating unit represented by following formula (2) containing (A-2);
[changing 2]
(in formula, R
1same as described above.)
The composition of the formation cured film described in 3.1 or 2, wherein, above-mentioned polymkeric substance also has the repeating unit represented by following formula (3);
[changing 3]
(in formula, R
3and R
3 'represent the alkyl of hydrogen atom or carbonatoms 1 ~ 3 independently of one another.R
4, R
4 'and R
5represent the alkyl of hydrogen atom, halogen atom or carbonatoms 1 ~ 5 independently of one another.)
The composition of the formation cured film according to any one of 4.1 ~ 3, wherein, also containing (E) ion-trapping agent;
The composition of the formation cured film according to any one of 5.1 ~ 4, wherein, also containing (F) multi-functional thiol compound;
6. the manufacture method of cured film, is characterized in that, the composition of the formation cured film according to any one of 1 ~ 5 is coated substrate, after irradiation ultraviolet radiation, burns till at 80 DEG C ~ 120 DEG C;
7. adopt the cured film that the manufacture method described in 6 manufactures;
8. film, it has the cured film described in 7.
The effect of invention
Composition of the present invention, owing to comprising the polymkeric substance with trialkoxy silane structure, therefore the hardness of cured film therefrom is high, excellent adhesion.In addition, by polyfunctional acrylic ester compound, hardness can be improved further.In addition, by containing multi-thiol compound, flexibility is excellent, and also can improve adaptation.Due to these, even if superfluously containing polyfunctional acrylic ester, be not also peeling and crackle.
Embodiment
Below further the present invention is explained.
< forms the composition > of cured film
The composition of formation cured film of the present invention comprises following (A) ~ (D) composition, as required containing more than a kind in following (E) ~ (G) composition, other additive.
< (A) composition >
(A) composition in composition of the present invention is the polymkeric substance that (A-1) has the repeating unit represented by following formula (1), can have the polymkeric substance of the repeating unit represented by following formula (2) as required containing (A-2).These polymkeric substance also can have the repeating unit represented by following formula (3) as required.
[changing 4]
(in formula, R
1represent hydrogen atom, methyl, chloro or phenyl independently of one another, R
2represent the alkyl of carbonatoms 1 ~ 5, L represents the alkylidene group of carbonatoms 1 ~ 9, R
3and R
3 'represent the alkyl of hydrogen atom or carbonatoms 1 ~ 3 independently of one another, R
4, R
4 'and R
5represent the alkyl of hydrogen atom, halogen atom or carbonatoms 1 ~ 5 independently of one another.)
When above-mentioned polymkeric substance has the repeating unit represented by formula (3), owing to giving adaptation and the such characteristic of hydrophobicity (low water absorbable) further to the composition of formation cured film of the present invention, therefore preferably.
In addition, the repeating unit shown in formula (1), the repeating unit shown in formula (2), the repeating unit shown in formula (3) can contain in a polymkeric substance simultaneously.
In the polymkeric substance used in composition of the present invention, the containing ratio of the repeating unit shown in formula (1), in whole repeating units of 100 % by mole, preferably 1 ~ 60 % by mole.When the containing ratio of the repeating unit shown in formula (1) is less than above-mentioned numerical range, the characteristic such as characteristic, cured film characteristic such as hardness of polymkeric substance of the present invention reduces sometimes.When the containing ratio of the repeating unit shown in formula (1) is larger than above-mentioned numerical range, the characteristic such as storage stability, adaptation of varnish reduces sometimes.
In the polymkeric substance used in composition of the present invention, the containing ratio of the repeating unit shown in formula (2), in whole repeating units of 100 % by mole, preferably 1 ~ 60 % by mole.When the containing ratio of the repeating unit shown in formula (2) is less than above-mentioned numerical range, the water-absorbent in the high temperature and humidity test of the characteristic of polymkeric substance of the present invention, cured film characteristic sometimes raises, and the characteristics such as the adaptation of long-term reliability reduce.When the containing ratio of the repeating unit shown in formula (2) is larger than above-mentioned numerical range, the characteristic such as adaptation reduces sometimes.
In the polymkeric substance used in composition of the present invention, the containing ratio of the repeating unit shown in formula (3), in whole repeating units of 100 % by mole, preferably 1 ~ 60 % by mole.When the containing ratio of the repeating unit shown in formula (3) is less than above-mentioned numerical range, the characteristic of polymkeric substance of the present invention, the characteristic such as hardness, adaptation of cured film characteristic reduce sometimes.When the containing ratio of the repeating unit shown in formula (3) is larger than above-mentioned numerical range, the characteristic such as adaptation reduces sometimes.
(A-1) polymkeric substance of composition will be by providing the monomer of the repeating unit shown in formula (1) and optional provide the monomer of the repeating unit shown in formula (3) etc. to be polymerized and manufacture.
In addition, the polymkeric substance of (A-2) composition will be by providing the monomer of the repeating unit shown in formula (2) and optional provide the monomer of the repeating unit shown in formula (3) etc. to be polymerized and manufacture.
Repeating unit shown in formula (1) ~ (3) comprises in a polymkeric substance simultaneously, by by providing the monomer of the repeating unit shown in above-mentioned formula (1), the monomer of the repeating unit shown in formula (2) is provided, the optional copolymerization such as the monomer of the repeating unit shown in above-mentioned formula (3) being provided and manufacturing.
As polymerization process, radical polymerization, anionoid polymerization, cationoid polymerisation etc. can be adopted.In these, particularly preferably radical polymerization, particularly, can in a solvent, under the existence of polymerization starter by above-mentioned polymerizable compound heating, make it be polymerized.
As the monomer providing the repeating unit shown in formula (1), such as vinylformic acid 3-trimethoxysilyl propyl ester, vinylformic acid 3-triethoxysilyl propyl ester, methacrylic acid 3-trimethoxysilyl propyl ester, methacrylic acid 3-triethoxysilyl propyl ester etc. can be enumerated.Wherein, from the view point of versatility-circulation, preferable methyl vinylformic acid 3-trimethoxysilyl propyl ester.
As the monomer providing the repeating unit shown in formula (2), vinylformic acid, methacrylic acid etc. can be enumerated.
As the monomer providing the repeating unit shown in formula (3), the distyryl compounds such as such as vinylbenzene, vinyl toluene, chloro-styrene, bromstyrol, 4-t-butyl styrene can be enumerated.
(A-1) and the polymkeric substance of (A-2) composition can comprise other repeating unit other than the above.As the monomer providing other repeating units, acrylic compound, methacrylate compound, maleimide compound, vinyl cyanide, maleic anhydride, vinyl compound etc. can be enumerated.Below enumerate its concrete example, but be not limited to these.
As acrylic compound, such as methyl acrylate can be enumerated, ethyl propenoate, isopropyl acrylate, benzyl acrylate, vinylformic acid naphthalene ester, vinylformic acid anthracene ester, vinylformic acid anthrylmethyl, phenyl acrylate, vinylformic acid 2,2,2-trifluoro ethyl ester, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, vinylformic acid 2-methoxy acrylate, methoxy triglycol acrylate, vinylformic acid 2-ethoxy ethyl ester, tetrahydrofurfuryl acrylate, vinylformic acid 3-methoxybutyl, vinylformic acid 2-methyl-2-adamantane esters, vinylformic acid 2-propyl group-2-adamantane esters, vinylformic acid 8-methyl-8-three ring decyl ester, vinylformic acid 2-hydroxy methacrylate, vinylformic acid 2-hydroxy propyl ester, vinylformic acid 2,3-dihydroxyl propyl ester, diethyleneglycol monoacrylate, vinylformic acid 4-hydroxybutyl, caprolactone 2-(acryloxy) ethyl ester, PEG ethyl ether acrylate, 5-acryloxy-6-hydroxy norbomene-2-carboxylic acid-6-lactone, vinylformic acid 8-ethyl-8-three ring decyl ester etc.
As methacrylate compound, such as methyl methacrylate can be enumerated, β-dimethyl-aminoethylmethacrylate, isopropyl methacrylate, benzyl methacrylate, methacrylic acid naphthalene ester, methacrylic acid anthracene ester, methacrylic acid anthrylmethyl, phenyl methacrylate, methacrylic acid 2,2,2-trifluoro ethyl ester, Tert-butyl Methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, methacrylic acid 2-methoxy acrylate, methoxy triglycol methacrylic ester, methacrylic acid 2-ethoxy ethyl ester, tetrahydrofurfuryl methacrylate, methacrylic acid 3-methoxybutyl, methacrylic acid 2-methyl-2-adamantane esters, gamma-butyrolactone methacrylic ester, methacrylic acid 2-propyl group-2-adamantane esters, methacrylic acid 8-methyl-8-three ring decyl ester, methacrylic acid 8-ethyl-8-three ring decyl ester, 2-hydroxyethyl methacrylate, methacrylic acid 2-hydroxy propyl ester, methacrylic acid 4-hydroxybutyl, methacrylic acid 2,3-dihydroxyl propyl ester, diethylene glycol monomethyl acrylate, caprolactone 2-(methacryloxy) ethyl ester, PEG ethyl ether methacrylate, 5-methacryloxy-6-hydroxy norbomene-2-carboxylic acid-6-lactone etc.
As vinyl compound, such as methylvinylether, benzyl vinyl ether, vinyl naphthalene, vinyl anthracene, vinyl biphenyl, vinylcarbazole, 2-hydroxyethyl vinyl ether, Vinyl phenyl ether, propyl vinyl ether etc. can be enumerated.
As maleimide compound, such as maleimide, N-methylmaleimido, N-phenylmaleimide, N-N-cyclohexylmaleimide etc. can be enumerated.
As with the monomer of monomer copolymerization that the repeating unit shown in formula (1) is provided, in above-claimed cpd, preferred acrylate compound, methacrylate compound, particularly preferably methyl methacrylate.
Above-mentioned polymerization starter can from known polymerization starter suitable choice for use.The superoxide such as such as benzoyl peroxide, cumene hydroperoxide, t-butyl hydroperoxide can be enumerated; The persulphates such as Sodium Persulfate, Potassium Persulphate, ammonium persulphate; The Azo etc. such as Diisopropyl azodicarboxylate, azo two (methylbutyronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-azo two (isopropylformic acid) dimethyl esters.These can a kind be used alone or two or more combinationally used.
The usage quantity of above-mentioned polymerization starter, relative to 1 mole of monomer, preferably about 0.005 ~ 0.05 mole.Temperature of reaction during polymerization suitably can set from 0 DEG C to the boiling point of the solvent used, but preferably about 20 ~ 100 DEG C.Reaction times is 0.1 ~ 30 hours preferably.
For the solvent of polyreaction, be not particularly limited, suitable choice for use in all kinds of SOLVENTS that generally can use from above-mentioned polyreaction.Particularly, water can be enumerated; The alcohols such as methyl alcohol, ethanol, 1-propyl alcohol, 2-propyl alcohol, n-butyl alcohol, 2-butanols, isopropylcarbinol, the trimethyl carbinol, 1-amylalcohol, 2-amylalcohol, 3-amylalcohol, primary isoamyl alcohol, tertiary amyl alcohol, 1-hexanol, 1-heptanol, 2-enanthol, 3-enanthol, sec-n-octyl alcohol, 2-ethyl-1-hexanol, benzylalcohol, hexalin; Anaesthetie Ether, Di Iso Propyl Ether, dibutyl ether, cyclopentyl-methyl ether, tetrahydrofuran (THF), Isosorbide-5-Nitrae-two
the ethers such as alkane; The halogenated hydrocarbons such as chloroform, methylene dichloride, ethylene dichloride, tetracol phenixin; The ether alcohol classes such as methylcyclohexane, ethyl cellosolve, ispropyl cellosolve, ethylene glycol butyl ether, diethylene glycol monobutyl ehter; The ketones such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), pimelinketone; The ester classes such as vinyl acetic monomer, N-BUTYL ACETATE, ethyl propionate, cellosolve acetate; The aliphatics or aromatic hydrocarbon based such as Skellysolve A, normal hexane, normal heptane, octane, n-nonane, n-decane, pentamethylene, methylcyclopentane, hexanaphthene, methylcyclohexane, benzene,toluene,xylene, ethylbenzene, phenylmethylether; The acetals such as methylal, acetal; The fatty acids such as formic acid, acetic acid, propionic acid; Nitropropane, oil of mirbane, dimethylamine, Monoethanolamine MEA BASF, pyridine, METHYLPYRROLIDONE, DMF, dimethyl sulfoxide (DMSO), acetonitrile etc.These can a kind be used alone or two or more kinds mixed.
The polymkeric substance used in the present invention, weight-average molecular weight is preferably 1, and 000 ~ 80,000, be more preferably 2,000 ~ 60,000, more preferably 3,000 ~ 50,000.If weight-average molecular weight is more than 80,000, the solvability sometimes for solvent reduces, and treatability reduces, if weight-average molecular weight is less than 1,000, sometimes become solidification deficiency during thermofixation, solvent resistance and thermotolerance reduce.
Further, weight-average molecular weight is the polystyrene conversion measured value adopting gel permeation chromatography (GPC).
Further, the polymkeric substance used in the present invention can be random copolymers, alternating copolymer, segmented copolymer any one.
< (B) composition >
(B) composition in composition of the present invention is polyfunctional acrylic ester compound.As the concrete example of such compound, dipentaerythritol acrylate can be enumerated, Dipentaerythritol hexamethacrylate, Dipentaerythritol Pentaacrylate, Dipentaerythritol pentamethacrylates, tetramethylol methane tetraacrylate, pentaerythritol tetramethylacrylate, pentaerythritol triacrylate, pentaerythritol acrylate trimethyl, pentaerythritol diacrylate, dimethyl pentaerythritol acrylate, tetra methylol tetraacrylate, tetra methylol propane tetramethyl-acrylate, tetramethylol methane tetraacrylate, tetramethylol methane tetramethyl-acrylate, Viscoat 295, trimethylolpropane trimethacrylate, 1, 3, 5-triacryl six hydrogen-S-triazine, 1, 3, 5-trimethacrylate acyl group six hydrogen-S-triazine, three (hydroxyethyl acryl) isocyanuric acid ester, the polyfunctional acrylic ester compounds such as three (hydroxy ethyl methyl acryl) isocyanuric acid ester.
Above-mentioned polyfunctional acrylic ester compound, as commercially available product, can easily obtain, and as its concrete example, can enumerate KAYARAD T-1420, KAYARAD DPHA, KAYARAD DPHA-2C, KAYARAD D-310, KAYARAD D-330, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60, KAYARAD DPCA-120, KAYARAD DN-0075, KAYARAD DN-2475, KAYARAD R-526, KAYARAD NPGDA, KAYARAD PEG400DA, KAYARAD MANDA, KAYARAD R-167, KAYARAD HX-220, KAYARAD HX620, KAYARAD R-551, KAYARAD R-712, KAYARADR-604, KAYARAD R-684, KAYARAD GPO-303, KAYARAD TMPTA, KAYARAD THE-330, KAYARAD TPA-320, KAYARAD TPA-330, KAYARAD PET-30, KAYARAD RP-1040 (being Japanese chemical drug (strain) manufacture above), ア ロ ニ ッ Network ス M-210, ア ロ ニ ッ Network ス M-240, ア ロ ニ ッ Network ス M-6200, ア ロ ニ ッ Network ス M-309, ア ロ ニ ッ Network ス M-400, ア ロ ニ ッ Network ス M-402, ア ロ ニ ッ Network ス M-405, ア ロ ニ ッ Network ス M-450, ア ロ ニ ッ Network ス M-7100, ア ロ ニ ッ Network ス M-8030, ア ロ ニ ッ Network ス M-8060, ア ロ ニ ッ Network ス M-1310, ア ロ ニ ッ Network ス M-1600, ア ロ ニ ッ Network ス M-1960, ア ロ ニ ッ Network ス M-8100, ア ロ ニ ッ Network ス M-8530, ア ロ ニ ッ Network ス M-8560, ア ロ ニ ッ Network ス M-9050 (above for East Asia synthesis (strain) manufactures), PVC ス コ ー ト 295, PVC ス コ ー ト 300, PVC ス コ ー ト 360, PVC ス コ ー ト GPT, PVC ス コ ー ト 3PA, PVC ス コ ー ト 400, PVC ス コ ー ト 260, PVC ス コ ー ト 312, PVC ス コ ー ト 335HP (being Osaka Organic Chemical Industry (strain) manufacture above) etc.In addition, these can use a kind or two or more combinationally used.
(B) content of composition, relative to 100 mass parts (A) composition, is preferably 10 ~ 300 mass parts, is more preferably 20 ~ 250 mass parts, is particularly preferably 30 ~ 200 mass parts.When this content is too small, the hardness property of cured film reduces, and when this ratio is excessive, the characteristic of adaptation and flexibility reduces, and easily cracks.
< (C) composition >
(C) composition is radical polymerization initiator, contributes to initiation or the promotion of the polymerization of (B) composition.
Radical polymerization initiator, as long as by rayed and/or can add the material that Thermal release causes radical polymerization.Such as, as optical free radical polymerization starter, benzophenone derivates, imdazole derivatives, double imidazole derivative, N-aryl glycine derivative, organic azide, two luxuriant titanium classes, aluminate complex compound, organo-peroxide, N-alkoxy pyridines can be enumerated
salt, thioxanthone derivates etc., more specifically, can enumerate benzophenone, 1,3-bis-(tertiary butyl dioxy carbonyl) benzophenone, 3,3', 4,4'-tetra-(tertiary butyl dioxy carbonyl) benzophenone ,-5-is different for 3-phenyl
oxazolone, 2-mercaptobenzimidazole, two (2, 4, 5-triphenyl) imidazoles, 2, 2-dimethoxy-1, 2-diphenylethane-1-ketone (trade(brand)name イ Le ガ キ ュ ア 651, BASF AG manufactures), 1-hydroxycyclohexylphenylketone (trade(brand)name イ Le ガ キ ュ ア 184, BASF AG manufactures), 2-benzyl-2-dimethylamino-1-(4-morphlinophenyl)-butane-1-ketone (trade(brand)name イ Le ガ キ ュ ア 369, BASF AG manufactures), two (η 5-2, 4-cyclopentadiene-1-base)-bis-(2, the fluoro-3-of 6-bis-(1H-pyrroles-1-base)-phenyl) titanium (trade(brand)name イ Le ガ キ ュ ア 784, BASF AG manufactures) etc., but be not limited to these.
In addition to the foregoing, also commercially available product can be used, particularly, the イ Le ガ キ ュ ア 907 that BASF AG manufactures can be enumerated, イ Le ガ キ ュ ア 379, イ Le ガ キ ュ ア 819, イ Le ガ キ ュ ア 127, イ Le ガ キ ュ ア 500, イ Le ガ キ ュ ア 754, イ Le ガ キ ュ ア 250, イ Le ガ キ ュ ア 1800, イ Le ガ キ ュ ア 1870, イ Le ガ キ ュ ア OXE01, DAROCURTPO, DAROCUR1173, the SpeedcureMBB that Lambson company manufactures, SpeedcurePBZ, SpeedcureITX, SpeedcureCTX, SpeedcureEDB, EsacureONE, Esacure KIP150, Esacure KTO46, the KAYACURE DETX-S that Japan's chemical drug (strain) manufactures, KAYACURECTX, KAYACURE BMS, KAYACURE DMBI etc.
In these, from the reason that adaptation improves, the particularly preferably mixture (trade(brand)name イ Le ガ キ ュ ア 500, BASF AG manufacture) of 1-hydroxycyclohexylphenylketone and benzophenone.
(C) content of the radical polymerization initiator of composition, relative to 100 mass parts (A) composition, is generally 1 ~ 20 mass parts, is preferably 1 ~ 15 mass parts.
< (D) solvent >
Use under the solution state that the composition of formation cured film of the present invention mainly dissolves in a solvent.As long as the solvent now used can dissolve (A) composition, (B) composition, (C) composition and optional (E) described later composition, (F) composition, (G) composition and other additives, be then not particularly limited.
As the concrete example of solvent, toluene, dimethylbenzene, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetic acid ester, ethylene glycol monomethyl ether, ethylene glycol bisthioglycolate ethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol isopropyl ether, ethylene glycol acetate, glycol ether methyl ethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl, 1 can be enumerated, 1,2-trichloroethane, 1,1,1,2-tetrachloroethane, 1,1,2,2-tetrachloroethane, methyl phenyl ether, Isosorbide-5-Nitrae-two
alkane, acetal, butanols, 2-butanols, primary isoamyl alcohol, methyl propyl ketone, methyl butyl ketone, methyl iso-butyl ketone (MIBK), metacetone, ethyl normal-butyl ketone, diη-propyl ketone, isobutyl acetate, n-butyl propionate, decane, dodecane, terpane, kautschin, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol bisthioglycolate butyl ether, ethylene glycol monobutyl ether acetic ester, ethylene glycol list phenyl ether, ethylene glycol mono hexyl ether, methoxymethoxy ethanol, glycol diacetate, glycol ether, diethylene glycol monomethyl ether, carbiphene, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ehter, diethylene glycol monobutyl ehter acetic ester, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, glycol ether acetic ester, triethylene glycol monomethyl ether, triglycol dichloride, propylene glycol, glycol monobutyl ether, 1-Butoxyethoxy propyl alcohol, dipropylene glycol, DPGME, dihydroxypropane single-ethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol mono butyl base ether, 1,3-PD, 1,3 butylene glycol, 2,3-butanediol, 1,5-PD, hexylene glycol, ethohexadiol, glycerine, hexachloroethane, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, 1,2,4-trichlorobenzene, o-dibromobenzene, Dichloroethyl ether, diisoamyl ether, n-hexyl ether, ethylphenyl ether, ethyl benzyl ether, eucalyptol (シ オ ネ ー Le), 1-octanol, sec-n-octyl alcohol, 2-Ethylhexyl Alcohol, 3,5,5-trimethyl hexanol, nonyl alcohol, nonylcarbinol, Exxal 12, 2 methyl cyclohexanol, benzylalcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, α-terpinol, rosin alcohol, acetonyl-acetone, sym.-diisopropylideneacetone, isophorone, methyl phenyl ketone, acetic acid methoxybutyl, acetic acid-2-ethylhexyl, cyclohexyl acetate, methyl cyclohexanol acetate, Benzyl Acetate, isoamyl acetate, butyl stearate, acetobutyric acid ethyl ester, isoamyl isovalerate, n-butyl lactate, isobutyl lactate, N_amyl lactate, isoamyl lactate, methyl benzoate, ethyl benzoate, propyl benzoate, wintergreen oil, dibutyl oxalate, diethyl malonate, butyryl oxide, valeric acid, isovaleric acid, caproic acid, 2-ethylhexyldithiophosphoric acid, capric acid, 2 ethyl hexanoic acid, Tricholroacetic Acid, lactic acid, oil of mirbane, cyanobenzene, Alpha-Methyl cyanobenzene, N-METHYLFORMAMIDE, N-methylacetamide, 2-Pyrrolidone etc.
Above-mentioned solvent, from the view point of printing, particularly preferably diethylene glycol monomethyl ether, carbiphene, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ehter, diethylene glycol monobutyl ehter acetic ester, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, glycol monobutyl ether, dipropylene glycol, DPGME, dihydroxypropane single-ethyl ether etc.
These solvents can a kind be used alone or two or more kinds mixed.In addition, the solvent used in the polymerization of (A) composition can also directly be used.
< (E) composition >
(E) composition is ion-trapping agent, prevents the metal wiring formed on substrate from causing migration by contacting with water.As such ion-trapping agent, preferably there is the compound with inner complex Forming ability of lone-pair electron in the structure, such as N can be enumerated, two [the 3-(3 of N'-, 5-di-tert-butyl-hydroxy phenyl) propionyl] hydrazine (IrganoxMD1024, BASF AG manufactures), two (benzylidiene hydrazide) (the Eastman Inhibitor OABH of oxalic acid, イ ー ス ト マ Application ケ ミ カ Le manufactures), 1, 2, 3-benzotriazole, 5-methyl isophthalic acid, 2, 3-benzotriazole, and ア デ カ タ プ ス CDA-1 (rising sun electrification (strain) manufacture), ア デ カ タ プ ア ス CDA-6 (rising sun electrification (strain) manufacture), Qunox (Mitsui east pressure Off ァ イ Application (strain) manufactures), NaugardXL-1 (ユ ニ ロ イ ア Le (strain) manufacture) etc.Especially, preferably 5-methyl isophthalic acid is used, 2,3-benzotriazole.
The content of above-mentioned ion-trapping agent, relative to polymkeric substance 100 mass parts of (A) composition, preferably 0.0001 ~ 20 mass parts, particularly preferably 0.001 ~ 10 mass parts.If less than 0.0001 mass parts, sometimes cannot obtain the effect of metal wiring protection, if more than 20 mass parts, sometimes make the characteristic such as hardness, adaptation as cured film reduce.In addition, on cost, sometimes also become unfavorable.
< (F) composition >
In the composition of formation cured film of the present invention, the multi-functional thiol's compound as (F) composition can be added as required.As above-mentioned multi-functional thiol's compound, preferably 3 officials can above mercaptan compound.Multi-functional thiol's compound can obtain as the addition reaction of polyvalent alcohol and simple function and/or multi-functional thiol's compound.As concrete compound, can 1 be enumerated, 3,5-tri-(3-mercaptopropionyl oxygen base ethyl)-isocyanuric acid ester, 1,3 functional thiols's compounds such as 3,5-tri-(3-sulfydryl butyryl acyloxy ethyl)-isocyanuric acid ester (Showa electrician (strain) manufacture, カ レ Application ズ MT (registered trademark) NR1), trimethylolpropane tris (3-mercaptopropionic acid ester); 4 functional thiols's compounds such as tetramethylolmethane four (3-mercaptopropionic acid ester), tetramethylolmethane four (3-mercaptobutylate) (Showa electrician (strain) manufacture, カ レ Application ズ MT (registered trademark) PEI); 6 functional thiols's compounds etc. such as Dipentaerythritol six (3-propionic ester).
The containing ratio of the multi-functional thiol's compound in composition of the present invention, preferably 0.1 ~ 8 quality %, more preferably 0.8 ~ 5 quality % in solids component.If containing ratio is beyond above-mentioned scope, the deterioration such as the stability of composition, smell, sensitivity, exploring clarity, resulting visualization, adaptation.Should illustrate, so-called solids component, refer to the composition getting rid of (D) solvent from whole compositions of the composition forming cured film.
< (G) composition >
In the composition of formation cured film of the present invention, the stopper as (G) composition can be added as required.As above-mentioned stopper, 2,6-diisobutyl phenol, 3,5-DI-tert-butylphenol compounds, 3,5-di-tertiary butyl methyl phenol, quinhydrones, Hydroquinone monomethylether, pyrogaelol, tert-butyl catechol, 4-methoxyl group-1-naphthols etc. can be enumerated.
The containing ratio of the stopper as (G) composition in composition of the present invention, preferably below 1 quality %, more preferably below 0.5 quality % in solids component.If containing ratio departs from above-mentioned scope, sometimes cause solidification bad, reaction becomes insufficient.
Other additives of < >
And then, cured film formation composition of the present invention, only otherwise damage effect of the present invention, the dissolution accelerators etc. such as the bonding auxiliary such as tensio-active agent, rheology modifier, silane coupling agent, pigment, dyestuff, preserving stabilizer, defoamer, polyphenol, polycarboxylic acid can be contained as required.
As tensio-active agent, be not particularly limited, such as fluorine system tensio-active agent, silicon system tensio-active agent, nonionic system tensio-active agent etc. can be enumerated.As this tensio-active agent, the commercially available product of such as Sumitomo ス リ ー エ system (strain) manufacture, large Japanese ink chemical industry (strain) manufacture or Asahi Glass (strain) manufacture etc. can be used.These commercially available products can easily obtain, therefore preferably.As its concrete example, the fluorine system tensio-active agent such as エ Off ト ッ プ EF301, EF303, EF352 ((strain) ジ ェ system コ manufactures), メ ガ Off ァ ッ Network F171, F173 (large Japanese ink chemical industry (strain) manufactures), Off ロ ラ ー De FC430, FC431 (Sumitomo ス リ ー エ system (strain) manufacture), ア サ ヒ ガ ー De AG710, サ ー Off ロ Application S-382, SC101, SC102, SC103, SC104, SC105, SC106 (Asahi Glass (strain) manufacture) can be enumerated.
The preferred example of the composition of formation cured film of the present invention is as described below.
[1] composition of cured film is formed, relative to 100 mass parts (A) composition, these are dissolved in (D) solvent by (E) composition of (B) composition containing 0.5 ~ 200 mass parts, (C) composition of 1 ~ 20 mass parts, 0.0001 ~ 20 optional mass parts.
[2] form the composition of cured film, in the composition of above-mentioned [1], also contain (F) composition with the scope of 0.1 ~ 8 quality % in solids component.
[3] form the composition of cured film, in the composition of above-mentioned [1] or [2], also contain (G) composition with below the 1 quality % in solids component.
The ratio of the solids component in the composition of formation cured film of the present invention, as long as each uniform composition ground dissolves in a solvent, is then not particularly limited, is preferably 1 ~ 80 quality %, is more preferably 5 ~ 60 quality %, more preferably 10 ~ 50 quality %.
The modulator approach of the composition of formation cured film of the present invention is not particularly limited.As an example, following method can be enumerated: by (A) component dissolves in (D) solvent, in ratio mixing (B) composition, (C) composition of regulation in this solution, also mix (E) composition etc. as required, make uniform solution.In addition, (F) composition, (G) composition and other compositions are added further in the suitable stage that can be set forth in this modulator approach and the modulator approach of mixing.
During the modulation of the composition of formation cured film of the present invention, the solution of (A) composition obtained by the polyreaction in solvent can be used as former state, under this situation, (B) composition, (C) composition is added as described above in the solution of this (A) composition, and then when adding (E) composition etc. as required and make uniform solution, in order to regulate concentration, can additional input further (D) solvent.Now, the solvent used in the synthesis of (A) composition is crossed can be identical with (D) solvent for concentration adjustment when forming the modulation of composition of cured film, also can difference.
The composition of the formation cured film of the solution state of such modulation, preferably uses aperture to be use after the strainer of about 0.2 μm etc. filters.
< film and cured film >
By by the composition of formation cured film of the present invention at substrate (such as, silicon/silicon dioxide is substrate coated, silicon nitride board, be coated with metal such as aluminium, molybdenum, the substrate of chromium etc., glass substrate, quartz base plate, ito substrate etc.), film (such as, tri acetyl cellulose membrane, polyester film, the resin moldings such as vinylformic acid mesentery) etc. on, adopt rotary coating, flowing coating, print roll coating, slot coated, the rotary coating continued with slit, ink-jet application, the coatings such as printing, then, with hot plate or baking oven etc. predrying (prebake), film can be formed.
By to light such as film irradiation ultraviolet radiations obtained above, thus carry out photocuring.The wavelength preferably 200 ~ 500nm of above-mentioned light, its exposure preferably 100 ~ 5,000mJ/cm
2.
Next, carry out for curing after thermofixation.Particularly, the heating such as hot plate or baking oven is used.As after cure, usually, adopt following method: under the Heating temperature selected from temperature 60 C ~ 150 DEG C, the scope of more preferably 80 DEG C ~ 120 DEG C, process 5 ~ 30 minutes when on hot plate, when in an oven, process 30 ~ 90 minutes.
By based on above-mentioned condition, the composition of formation cured film of the present invention is solidified, the step discrepancy in elevation planarization fully of substrate can be made, the cured film with high transparent can be formed.
In addition; the composition of formation cured film of the present invention is owing at least having the smooth voltinism of necessary level, hardness and adaptation; therefore also can be used as the material of the cured film such as protective membrane, planarization film, insulating film formed in the various indicating meters such as thin film transistor (TFT) type liquid crystal display device, organic EL; especially, the top layer material of ito film is suitable as.
Use the cured film that the composition of formation cured film of the present invention obtains, owing to comprising the polymkeric substance with trialkoxy silane structure, therefore hardness is high, excellent adhesion.In addition, utilize polyfunctional acrylic ester, hardness can be improved further.In addition, by containing multi-thiol compound, flexibility is excellent, also can improve adaptation further.Due to these, even if superfluously containing polyfunctional acrylic ester, be not also peeling and crackle.Further, this film is good due to the transparency, therefore also can be applicable to being used in flexible display, touch pad.
Embodiment
Below enumerate synthesis example, embodiment and comparative example, the present invention will be described in more detail, but the present invention is not limited to these embodiments.
Should illustrate, Showa electrician (strain) is used to manufacture GPC device (Shodex GPC-101) (post: Shodex (registered trademark) KF803L and KF804L (Showa electrician (strain) manufacture)), with within flow 1mL/ minute, to make making stripping solvents tetrahydrofurane flow into (column temperature 40 DEG C) in post its molten from condition under, measure the weight-average molecular weight (Mw) of the polymkeric substance obtained in synthesis example.Mw polystyrene conversion value represents.
In addition, the reagent used in following synthesis example, embodiment, comparative example and device as described below.
DEGMEA (diethylene glycol monoethyl ether acetate), MMA (methyl methacrylate), MAA (methacrylic acid), ST (vinylbenzene), tBuST (4-t-butyl styrene): Tokyo changes into industry (strain) manufacture.
KBM-503:3-methacryloxypropyl trimethoxy silane, SHIN-ETSU HANTOTAI's chemical industry (strain) manufacture.
MAIB:2,2'-azo two (isopropylformic acid) dimethyl ester, Tokyo change into industry (strain) manufacture.
PET-30: pentaerythritol triacrylate/tetramethylol methane tetraacrylate, Japanese chemical drug (strain) manufacture.
DPHA: dipentaerythritol acrylate/Dipentaerythritol Pentaacrylate (カ ヤ ラ De DPHA, Japanese chemical drug (strain) manufacture).
IRG500: the イ Le ガ キ ュ ア 500 that Photoepolymerizationinitiater initiater, BASF AG manufacture.
IRG651: the イ Le ガ キ ュ ア 651 that Photoepolymerizationinitiater initiater, BASF AG manufacture.
PE1: chain-transfer agent, Showa electrician (strain) manufacture, カ レ Application ズ MT-PE1.
MBTA:5-methyl isophthalic acid, 2,3-benzotriazole, Tokyo change into industry (strain) manufacture.
4-MNP:4-methoxyl group-1-naphthols, Tokyo change into industry (strain) manufacture.
AGITAN771: defoamer, MUNZING society manufacture.
Whipping appts: (strain) シ ン キ ー manufactures あ わ と り And-chain Taro ARE-310.
Z320: ダ イ セ Le サ イ テ ッ Network (strain) manufactures サ イ Network ロ マ ー P.
The synthesis of [synthesis example 1-7] resin
[synthesis example 1]
In the four-hole boiling flask of 1,000mL, load 375.8gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 300gMMA and 7.5gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P1.Mw=about 30,000.
[synthesis example 2]
In the four-hole boiling flask of 1,000mL, load 436.1gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 270gMMA, 78.1gKBM-503 and 8.7gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P2.Mw=about 20,000 5 thousand.
[synthesis example 3]
In the four-hole boiling flask of 1,000mL, load 476.3gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 280gMMA, 29.8gMAA and 7.7gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P3.Mw=about 30,000.
[synthesis example 4]
In the four-hole boiling flask of 1,000mL, load 424.5gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 190gMMA, 63.5gKBM-503,86.9g tBuST and 6.9gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P4.Mw=about 20,000.
[synthesis example 5]
In the four-hole boiling flask of 1,000mL, load 460.7gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 230gMMA, 24.7gMAA, 46g tBuST and 6.4gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P5.Mw=about 20,000.
[synthesis example 6]
In the four-hole boiling flask of 1,000mL, load 424.5gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 190gMMA, 63.5gKBM-503,56.5g ST and 6.9gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P6.Mw=about 20,000.
[synthesis example 7]
In the four-hole boiling flask of 1,000mL, load 460.7gDEGMEA, stir under nitrogen atmosphere, under 80 DEG C (interior temperature).Last the mixed solution that 2 hours instill 230gMMA, 24.7gMAA, 30g ST and 6.4gMAIB wherein at leisure.Make it react 20 hours after instillation, obtain resin solution P7.Mw=about 20,000.
[embodiment 1-8, comparative example 1] forms the making of composition of cured film, the making of cured film and evaluation thereof
The IRG500 of PE1,0.54g of DHPA, the 0.54g of resin solution P2, the 5.4g obtained in the synthesis example 2 of 20g is loaded in the plastic containers of 200mL, loaded in whipping appts, stir 10 minutes with 2,000rpm, make varnish (embodiment 1).
Similarly, varnish (embodiment 2-8, comparative example 1) is made by the composition shown in table 1.
[table 1]
[forming the evaluation of the composition of cured film]
Above-mentioned resin combination is held in vacuum (strain) ito film (resistive film (high transmission) ito film, resistance value: 400 ± 100 Ω/sq, all-optical transmittance: > 90%) that manufactures three and carries out rod coaters coating to make thickness become about 3 ~ 10 μm, first at 110 DEG C, carried out 5 minutes prebake.Next, UV irradiation (400mJ/cm is carried out
2), cure after then carrying out 55 minutes at 110 DEG C, make cured film.
For the cured film obtained, the evaluation of adaptation that adopted following method to carry out.
[with the evaluation of the adaptation of ITO]
Adopt the evaluation of cross cut test method.First, use cutters, make 100 checkerboard grid in coated film.Next, セ ロ Ha ン テ ー プ (registered trademark) that bonding ニ チ バ Application (strain) manufactures on this checkerboard grid, rubs consumingly from top rubber, makes it closely sealed fully.Then, next セ ロ Ha ン テ ー プ (registered trademark) is peeled off, have several stripping to evaluate with in now 100 checkerboard grid.
0B:66 above stripping
1B:36 ~ 65 strippings
2B:16 ~ 35 strippings
3B:6 ~ 15 strippings
4B:1 ~ 5 strippings
5B: without peeling off
Above evaluation result is shown in table 2.
[table 2]
Adaptation | |
Embodiment 1 | 1B |
Embodiment 2 | 3B |
Embodiment 3 | 3B |
Embodiment 4 | 5B |
Embodiment 5 | 5B |
Embodiment 6 | 5B |
Embodiment 7 | 5B |
Embodiment 8 | 5B |
Comparative example 1 | 0B |
From the result shown in table 2, the adaptation of the cured film obtained by the composition forming cured film of embodiment 1 ~ 8 is higher than comparative example.
The synthesis of [synthesis example 8-11] resin
[synthesis example 8]
1, load 454.9gDEGMEA in the four-hole boiling flask of 000mL, under nitrogen atmosphere, last the mixed solution that 2 hours instill 250.0gMMA, 91.5g tBuST, 70.9g KBM-503 and 9.9gMAIB wherein at leisure while stirring under 80 DEG C (interior temperature).At 80 DEG C, make it react 20 hours after instillation again, obtain resin solution P8.Mw=about 30,000.
[synthesis example 9]
In the four-hole boiling flask of 1,000mL, load 506.5gDEGMEA, under nitrogen atmosphere, last the mixed solution that 2 hours instill 250.0gMMA, 50.0g tBuST, 26.9g MAA and 10.8gMAIB wherein at leisure while stirring under 80 DEG C (interior temperature).At 80 DEG C, make it react 20 hours after instillation again, obtain resin solution P9.Mw=about 30,000.
[synthesis example 10]
In the four-hole boiling flask of 1,000mL, load 520.0gDEGMEA, under nitrogen atmosphere, last the mixed solution that 2 hours instill 250.0gMMA, 74.6g ST, 88.6g KBM-503 and 12.3gMAIB wherein at leisure while stirring under 80 DEG C (interior temperature).At 80 DEG C, make it react 20 hours after instillation again, obtain resin solution P10.Mw=about 30,000.
[synthesis example 11]
In the four-hole boiling flask of 1,000mL, load 480.4gDEGMEA, under nitrogen atmosphere, last the mixed solution that 2 hours instill 250.0gMMA, 32.6g ST, 26.9g MAA and 10.8gMAIB wherein at leisure while stirring under 80 DEG C (interior temperature).At 80 DEG C, make it react 20 hours after instillation again, obtain resin solution P11.Mw=about 30,000.
[embodiment 9-14, comparative example 2-4] forms the making of the composition of cured film, the making of cured film and evaluation thereof
The DEGMEA of AGITAN771,14.7g of MBTA, 0.03g of PE1,0.02g of IRG500,3.1g of PET-30, the 3.1g of resin solution P9, the 17.8g obtained in the synthesis example 9 of resin solution P8, the 50.9g obtained in the synthesis example 8 of 11.3g is loaded in the plastic containers of 200mL, loaded in whipping appts, 2, stir 10 minutes under 000rpm, make varnish (embodiment 9).
Similarly, by the composition shown in table 3, make varnish (embodiment 10-14, comparative example 2-4).
[table 3]
[making of cured film]
Above-mentioned varnish is held in vacuum (strain) ito film (resistive film (high transmission) ito film, resistance value: 400 ± 100 Ω/sq, all-optical transmittance: > 90%) that manufactures three and carries out rod coaters coating to make thickness become about 3 ~ 10 μm, first at 110 DEG C, carried out 10 minutes prebake.Next UV irradiation (400mJ/cm is carried out
2), cure after then carrying out 50 minutes at 110 DEG C, make cured film.
For the cured film obtained, following method is adopted to carry out the evaluation of pencil hardness, adaptation, flexibility.
[evaluation of pencil hardness]
According to JIS K 5400, measure by 1,000g load.Show the result in table 4.
[with the evaluation of the adaptation of ITO]
Adopt the evaluation of cross cut test method.First, use cutters, be made 100 checkerboard grid in coated film.Next, セ ロ Ha ン テ ー プ (registered trademark) that bonding ニ チ バ Application (strain) manufactures on this checkerboard grid, rubs consumingly from top rubber, makes it closely sealed fully.Then, next セ ロ Ha ン テ ー プ (registered trademark) is peeled off, have several stripping to evaluate with in now 100 checkerboard grid.Show the result in table 4.
0B:66 above stripping
1B:36 ~ 65 strippings
2B:16 ~ 35 strippings
3B:6 ~ 15 strippings
4B:1 ~ 5 strippings
5B: without peeling off
[evaluation of flexibility]
Take coated side as outside, diametrically film is fixed 15 seconds by the cylinder of 4cm.Observe the change of the outward appearance of film, vicissitudinous situation will do not had to be designated as zero, the situation creating crackle is designated as ×.Show the result in table 4.
[table 4]
Pencil hardness | Adaptation | Flexibility | |
Embodiment 9 | F | 4B | ○ |
Embodiment 10 | F | 5B | ○ |
Embodiment 11 | F | 4B | ○ |
Embodiment 12 | H | 5B | ○ |
Embodiment 13 | F | 4B | ○ |
Embodiment 14 | 2H | 5B | ○ |
Comparative example 2 | <HB | 2B | ○ |
Comparative example 3 | 3H | 0B | × |
Comparative example 4 | H | 0B | × |
From the result shown in table 4, the pencil hardness of the cured film obtained by the composition forming cured film of embodiment 9 ~ 14 is all up to more than F, and adaptation is also up to more than 4B, and flexibility is also good.
On the other hand, for comparative example 2 ~ 4, adaptation is low reaches below 2B, fail to meet pencil hardness, adaptation, flexibility whole.
Claims (8)
1. form the composition of cured film, it is characterized in that, contain:
(A) (A-1) has by the polymkeric substance of the repeating unit shown in following formula (1),
In formula, R
1represent hydrogen atom, methyl, chloro or phenyl, R
2represent the alkyl of carbonatoms 1 ~ 5, L represents the alkylidene group of carbonatoms 1 ~ 9,
(B) polyfunctional acrylic ester compound,
(C) radical polymerization initiator, and
(D) solvent.
2. the composition of formation cured film according to claim 1, wherein, as (A) composition, also has by the polymkeric substance of the repeating unit shown in following formula (2) containing (A-2),
In formula, R
1same as described above.
3. the composition of the formation cured film described in claim 1 or 2, wherein, above-mentioned polymkeric substance also has by the repeating unit shown in following formula (3),
In formula, R
3and R
3 'represent the alkyl of hydrogen atom or carbonatoms 1 ~ 3 independently of one another, R
4, R
4 'and R
5represent the alkyl of hydrogen atom, halogen atom or carbonatoms 1 ~ 5 independently of one another.
4. the composition of the formation cured film described in any one of claims 1 to 3, wherein, also containing (E) ion-trapping agent.
5. the composition of the formation cured film described in any one of Claims 1 to 4, wherein, also containing (F) multi-functional thiol compound.
6. the manufacture method of cured film, is characterized in that, the composition of the formation cured film described in any one of Claims 1 to 5 is coated substrate, after irradiation ultraviolet radiation, burns till at 80 DEG C ~ 120 DEG C.
7. adopt the cured film that manufacture method according to claim 6 manufactures.
8. film, it has cured film according to claim 7.
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JP2012008262A (en) * | 2010-06-23 | 2012-01-12 | Fujifilm Corp | Colored photosensitive resin composition, pattern forming method, manufacturing method of color filter, color filter, and display device comprising the same |
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JP2008255180A (en) * | 2007-04-03 | 2008-10-23 | Toyo Ink Mfg Co Ltd | Active energy ray-curing resin composition and laminate thereof |
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JPH06287470A (en) * | 1993-04-05 | 1994-10-11 | Mitsubishi Petrochem Co Ltd | Abrasion resistive coating composition |
JPH08245903A (en) * | 1995-03-10 | 1996-09-24 | Dainippon Ink & Chem Inc | Silver-coating resin composition curable by actinic energy ray |
JP2009215364A (en) * | 2008-03-07 | 2009-09-24 | Fujifilm Corp | Photocurable composition, and adhesion method and method for manufacturing liquid crystal panel using the same |
CN101851388A (en) * | 2009-03-31 | 2010-10-06 | 日立化成工业株式会社 | Electronic component-use liquid resin composition and electronic part apparatus |
JP2012008262A (en) * | 2010-06-23 | 2012-01-12 | Fujifilm Corp | Colored photosensitive resin composition, pattern forming method, manufacturing method of color filter, color filter, and display device comprising the same |
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TW201422654A (en) | 2014-06-16 |
JPWO2014034516A1 (en) | 2016-08-08 |
KR20150052080A (en) | 2015-05-13 |
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