WO2019146421A1 - 光硬化性シーリング用材料 - Google Patents
光硬化性シーリング用材料 Download PDFInfo
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- WO2019146421A1 WO2019146421A1 PCT/JP2019/000580 JP2019000580W WO2019146421A1 WO 2019146421 A1 WO2019146421 A1 WO 2019146421A1 JP 2019000580 W JP2019000580 W JP 2019000580W WO 2019146421 A1 WO2019146421 A1 WO 2019146421A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- meth
- sealing material
- photocurable sealing
- bis
- Prior art date
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- 239000003566 sealing material Substances 0.000 title claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 229920006295 polythiol Polymers 0.000 claims abstract description 50
- 238000012360 testing method Methods 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 63
- -1 carbodiimide compound Chemical class 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 44
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 29
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- 239000000853 adhesive Substances 0.000 claims description 15
- 229920000728 polyester Polymers 0.000 claims description 13
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 6
- 238000000016 photochemical curing Methods 0.000 claims description 6
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 230000000694 effects Effects 0.000 abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 20
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 10
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 10
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 238000007789 sealing Methods 0.000 description 10
- 229940071127 thioglycolate Drugs 0.000 description 10
- 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 9
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000007870 radical polymerization initiator Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910001507 metal halide Inorganic materials 0.000 description 6
- 150000005309 metal halides Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 6
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 5
- HAQZWTGSNCDKTK-UHFFFAOYSA-N 2-(3-sulfanylpropanoyloxy)ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOC(=O)CCS HAQZWTGSNCDKTK-UHFFFAOYSA-N 0.000 description 5
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 5
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
- 230000001678 irradiating effect Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 4
- JDGWMLZPJJXMCC-UHFFFAOYSA-N 3-phenyl-3-sulfanylpropanoic acid Chemical compound OC(=O)CC(S)C1=CC=CC=C1 JDGWMLZPJJXMCC-UHFFFAOYSA-N 0.000 description 4
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical class CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 4
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical class C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- RBNOTYQMZAVTTN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;2-methyloxirane Chemical compound CC1CO1.OCC1CCC(CO)CC1 RBNOTYQMZAVTTN-UHFFFAOYSA-N 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 239000007983 Tris buffer Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229960004337 hydroquinone Drugs 0.000 description 3
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
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- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- LBDSQNRQXIKAGX-UHFFFAOYSA-N (2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(C)COC(=O)C=C LBDSQNRQXIKAGX-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- STFXXRRQKFUYEU-UHFFFAOYSA-N 16-methylheptadecyl prop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C=C STFXXRRQKFUYEU-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- JTMBCYAUSCBSEY-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanoic acid Chemical compound CC(C)(S)C(O)=O JTMBCYAUSCBSEY-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 2
- ZBQGMMDOBGOEHH-UHFFFAOYSA-N 3-methyl-3-sulfanylbutanoic acid Chemical compound CC(C)(S)CC(O)=O ZBQGMMDOBGOEHH-UHFFFAOYSA-N 0.000 description 2
- PTPQZNNAUUSACC-UHFFFAOYSA-N 3-sulfanylpentanoic acid Chemical compound CCC(S)CC(O)=O PTPQZNNAUUSACC-UHFFFAOYSA-N 0.000 description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 2
- NEAFWRKPYYJETG-UHFFFAOYSA-N 4-sulfanylpentanoic acid Chemical compound CC(S)CCC(O)=O NEAFWRKPYYJETG-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical class C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- UUAGPGQUHZVJBQ-UHFFFAOYSA-N Bisphenol A bis(2-hydroxyethyl)ether Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 UUAGPGQUHZVJBQ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
- UCHGOTBQZQAGBC-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;oxirane Chemical compound C1CO1.OCC1CCC(CO)CC1 UCHGOTBQZQAGBC-UHFFFAOYSA-N 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 2
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- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical class [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
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- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
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- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
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- 150000002220 fluorenes Chemical class 0.000 description 1
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
- XTBJSRPRFRBLIP-UHFFFAOYSA-N hexane-1,6-diol;pentane-1,5-diol Chemical compound OCCCCCO.OCCCCCCO XTBJSRPRFRBLIP-UHFFFAOYSA-N 0.000 description 1
- MHLUCOKRQATVES-UHFFFAOYSA-N hexane-2,5-dithiol Chemical compound CC(S)CCC(C)S MHLUCOKRQATVES-UHFFFAOYSA-N 0.000 description 1
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- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
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- BHPYRDLULHDSET-UHFFFAOYSA-N methoxymethane;prop-2-enoic acid Chemical compound COC.OC(=O)C=C.OC(=O)C=C BHPYRDLULHDSET-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
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- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical class C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- 150000003303 ruthenium Chemical class 0.000 description 1
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- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
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- 150000004897 thiazines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1012—Sulfur-containing polymers, e.g. polysulfides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
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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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1021—Polyurethanes or derivatives thereof
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16J—PISTONS; CYLINDERS; SEALINGS
- F16J15/00—Sealings
- F16J15/02—Sealings between relatively-stationary surfaces
- F16J15/06—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces
- F16J15/10—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces with non-metallic packing
- F16J15/102—Sealings between relatively-stationary surfaces with solid packing compressed between sealing surfaces with non-metallic packing characterised by material
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16J—PISTONS; CYLINDERS; SEALINGS
- F16J15/00—Sealings
- F16J15/02—Sealings between relatively-stationary surfaces
- F16J15/14—Sealings between relatively-stationary surfaces by means of granular or plastic material, or fluid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2003/1034—Materials or components characterised by specific properties
- C09K2003/1062—UV-curable materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2003/1034—Materials or components characterised by specific properties
- C09K2003/1081—Water-proofed materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
Definitions
- the present invention relates to a photocurable sealing material. More particularly, the present invention relates to a photocurable sealing material having excellent sealing properties such as waterproofness.
- Conventional sealing materials include, for example, hot melt adhesives, one-component urethane-based reactive hot melt adhesives, thermoplastic hot melt sealing materials, moisture-curable hot melt sealing materials, thermosetting sealing materials, two-liquid Type urethane based foam sealing materials etc. are known. But none of them Insufficient heat resistance and waterproofness etc.
- the operability such as prevention of moisture contamination is complicated, Need equipment for heating, Concern about thermal damage to the case, The operability of manufacturing using a mold is complicated, There is a problem such as that there is no one that can provide a sufficiently satisfactory sealing property to a housing such as an electronic component, a home appliance, a precision instrument, etc., and its provision is desired.
- the photocurable sealing material can be manufactured on the housing without using a mold, and therefore, it is superior in operability and mass productivity as compared with conventional sealing materials.
- the photocurable sealing materials mainly include photocurable sealing materials using radical polymerization of acryloyl group and ene-thiol based photocurable sealing materials using ene-thiol reaction.
- the photocurable sealing material using radical polymerization of acryloyl group is produced, for example, by curing a composition comprising a urethane acrylate oligomer, an acrylate monomer, a photopolymerization initiator (and a photosensitizer) with light or the like.
- An object of the present invention is to provide a photocurable sealing material which is excellent in airtightness and waterproofness.
- the present inventors should solve the said subject, it is a photocurable sealing material which contains a polythiol compound at least as a 1st component, Comprising: In the predetermined size using the said photocurable sealing material When sheets were produced, those showing predetermined self-adhesiveness and self-adhesive strength were found to be particularly excellent in airtightness and waterproofness, and the present invention was completed. That is, the present invention is as follows.
- a photocurable sealing material comprising at least a polythiol compound as a first component
- Two sheets of 1 mm in thickness, 25 mm in width and 200 mm in length are prepared using the above-mentioned photocurable sealing material, irradiated with ultraviolet rays and photocured, and then the two sheets are laminated to obtain 10 kg.
- the laminated interface of the above two sheets disappears, and the self-adhesive strength in the T-peel test is 5 N / 25 mm or more when pulled at a peel rate of 300 mm / min.
- the second component comprises a second component and a third component, and further comprises a fourth component and / or a fifth component
- the second component is an oligomer having a (meth) acryloyl group having a weight average molecular weight of 1,000 to 30,000
- the third component is a monomer having a (meth) acryloyl group
- the fourth component is a photo radical polymerization initiator
- the fifth component is a viscosity modifier, 5 to 100 parts by mass of the third component with respect to 100 parts by mass of the second component,
- the ratio of the total number of (meth) acryloyl groups contained in both the second component and the third component to the total number of mercapto groups in the first component is 100: 5 n to 100: 25 n (n is the above-mentioned polythiol
- the photocurable sealing material according to any one of [1] to [3], which is the number of mercapto groups in one molecule of the compound.
- the second component is a urethane (meth) acrylate oligomer, a polyester (meth) acrylate oligomer, a polyether (meth) acrylate oligomer, a (meth) acrylic (meth) acrylate oligomer, an epoxy (meth) acrylate
- the photocurable sealing material according to [4] or [5] further comprising 0.1 to 15 parts by mass of a carbodiimide compound as a sixth component with respect to 100 parts by mass of the second component.
- the photocurable sealing material according to the present embodiment is a photocurable sealing material containing at least a polythiol compound as a first component, and is 1 mm thick, 25 mm wide, and long using the photocurable sealing material.
- a photocurable sealing material which exhibits an action to disappear and whose self-adhesive strength in a T-peel test is 5 N / 25 mm or more when pulled at a peel rate of 300 mm / min.
- the light-curable sealing material exhibits a predetermined self-adhesiveness by providing such a configuration, and exhibits an effect of being excellent in airtightness and waterproofness.
- the airtightness and waterproofness may be collectively referred to as "sealing characteristics".
- laminated interface means an interface where the two sheets face each other and are superimposed on each other.
- Self-adhesiveness refers to the property that when the two sheets are laminated, the two sheets are joined together and integrated so that the laminated interface becomes indistinguishable (characteristic that the laminated interface disappears) . That is, the above-mentioned photocurable sealing material is produced by irradiating two sheets with the above-mentioned conditions, photocuring them by irradiating ultraviolet rays, laminating the above two sheets and applying a load of 10 kg for 10 seconds If it does, it can also be understood as showing self-adhesiveness.
- ultraviolet rays irradiated to the two sheets for photocuring ultraviolet rays emitted from a metal halide light source are used.
- a metal halide light source for example, an electrodeless metal halide lamp type UV irradiation apparatus (trade name: FOTOCURE TFL-150) manufactured by Tokyo Hotton Co., Ltd. can be mentioned.
- the UV-A integrated light quantity of the ultraviolet light for photocuring the two sheets at the time of confirming the action of disappearance of the laminated interface of the two sheets is 6000 mJ / cm 2 .
- the load of 10 kg to be applied when laminating the two sheets is performed by uniformly applying to the main surface of the sheet.
- a tensile tester manufactured by Orientec Co., Ltd. now A & D Co., Ltd.
- a & D Co., Ltd. can be mentioned.
- the "self-adhesive strength" means the breaking strength of the two stacked sheets.
- the self-adhesive strength is 5 N / 25 mm or more, preferably 15 N / 25 mm or more, when pulled at a peeling speed of 300 mm / min.
- the self-adhesive strength is preferably 40 N / 25 mm or more, more preferably 80 N / 25 mm or more, when it is pulled at a peeling speed of 300 mm / min.
- the upper limit of self-adhesive strength is, for example, preferably 1000 N / 25 mm or less when pulled at a peeling speed of 300 mm / min, more preferably 800 N / 25 mm or less, and still more preferably 300/25 mm or less .
- the T-peel test for measuring the self-adhesive strength is performed using a tensile tester (manufactured by ORIENTEC Co., Ltd. (now A & D Co., Ltd., trade name: RTC-1310A).
- the polythiol compound which is the first component means a compound having two or more mercapto groups.
- the polythiol compound include polythiol compounds having 2 to 10 mercapto groups in the molecule.
- polythiol compounds having 2 to 6 mercapto groups in the molecule can be mentioned.
- polythiol compounds having 3 to 4 mercapto groups in the molecule can be mentioned.
- the polythiol compound is specifically described below.
- Examples of the polythiol compound include (A) Polythiol compounds having a hydrocarbon structure (aliphatic polythiols such as C 2-20 alkane polythiols, araliphatic polythiols such as xylylene dithiols, halogen atoms of halohydrin adducts of alcohols are substituted with mercapto groups Polythiols, polythiol compounds consisting of hydrogen sulfide reaction products of polyepoxide compounds, etc.), (B) Polythiol compounds containing an ether structure represented by Formula (1), and (c) Polythiol compounds containing an ester structure represented by Formula (2).
- A Polythiol compounds having a hydrocarbon structure (aliphatic polythiols such as C 2-20 alkane polythiols, araliphatic polythiols such as xylylene dithiols, halogen atoms of halohydr
- R 1 and R 2 independently represent a hydrogen atom or a C 1-10 alkyl group, m is 0, 1 or 2 and p is 0 or 1 is there.
- the expressions “C 2-20 ” and “C 1-10 ” mean that the carbon number is 2 to 20 and 1 to 10, respectively (the same applies hereinafter).
- Preferred compounds among these polythiol compounds (a) to (c) include a polythiol compound (b) containing an ether structure and a polythiol compound (c) containing an ester structure, and more preferably a polythiol compound containing an ester structure c).
- polythiol compound (a) having a hydrocarbon structure examples include 2,5-hexanedithiol, 2,9-decanedithiol, 1,4-bis (1-mercaptoethyl) benzene and the like.
- polythiol compound (b) containing an ether structure for example, 2-mercaptoethyl ether group, 2-mercaptopropyl ether group, 3-mercaptopropyl ether group, 2-mercaptobutyl ether group, 3-mercaptobutyl ether group, 4-mercapto Examples thereof include compounds having a structure such as butyl ether group, 5-mercaptopentyl ether group and 5-mercaptohexyl ether group.
- the polythiol compound (c) containing an ester structure is produced by esterifying a mercapto group-containing carboxylic acid, which is a compound in which a hydrogen atom is bonded to the left end of the structure of formula (2), and a polyhydric alcohol It contains a compound.
- polyhydric alcohol is meant a compound comprising two or more hydroxyl groups.
- mercapto group-containing carboxylic acid which is a compound in which a hydrogen atom is bonded to the left end of the structure of the formula (2)
- thioglycolic acid 2-mercaptopropionic acid, 3-mercaptobutyric acid, 2-mercaptoisobutyric acid 3-mercaptoisobutyric acid, 3-mercaptopropionic acid, 3-mercapto-3-phenylpropionic acid, 3-mercapto-3-methylbutyric acid and the like
- 3-mercaptobutyric acid, 3-mercapto-3-phenylpropionate Acids, 3-mercapto-3-methylbutyric acid and the like can be mentioned. More preferably, 3-mercaptobutyric acid is mentioned.
- C2-20 alkylene glycol ( C2-10 alkylene group is preferable and the carbon chain may be branched.
- examples include ethylene glycol, trimethylene glycol, 1,2-propylene glycol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, tetramethylene glycol, 1,5-pentanediol 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,12-dodecanediol, cyclohexane-1,4-dimethanol, hydrogenated bisphenol A, etc.), diethylene glycol , Poly (oxyalkylene) glycol, glycerin, triethy Glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol, poly
- alkylene glycols having 2 carbon atoms in the alkylene main chain such as ethylene glycol, 1,2-propylene glycol, 1,2-butanediol, etc., trimethylolpropane, polycarbonate diol, cyclohexane diol, cyclohexane di Methanol, 1,5-pentanediol and the like can be mentioned.
- aromatic ring-containing polyols examples include 2,2-bis [4- (2-hydroxyethyloxy) phenyl] propane, 4,4 ′-(9-fluorenylidene) diphenol, and 4,4 ′-(9- And fluorenylidene) bis (2-phenoxyethanol).
- the polythiol compound represented by Formula (3) and Formula (4) is mentioned.
- R 3 to R 6 independently represent a hydrogen atom or a C 1-10 alkyl group.
- L- (CO) -O- represents a structure represented by the above-mentioned formula (2).
- C 1-10 alkyl group of R 3 to R 6 in the formula (3) a linear or branched C 1-3 alkyl group is preferable.
- Specific examples of the C 1-10 alkyl group include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Among these, a methyl group and an ethyl group are preferable.
- Particularly preferred is a polythiol compound in which R 3 is a hydrogen atom, a methyl group or an ethyl group, and all of R 4 to R 6 are hydrogen atoms.
- polythiol compounds represented by the formulas (3) and (4) include ethylene glycol bis (3-mercaptobutyrate), propylene glycol bis (3-mercaptobutyrate), and diethylene glycol bis (3-mercaptobutylate).
- polythiol compounds containing two or more 3-mercaptobutyrate groups are preferred, and particularly polyethylene glycol bis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptobutyrate), dipentaerythritol Hexakis (3-mercaptobutyrate) or the like is preferred.
- polyethylene glycol bis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptobutyrate), dipentaerythritol Hexakis (3-mercaptobutyrate) or the like is preferred.
- the structures of specific examples of preferred polythiol compounds are shown in the following formulas (5) to (14).
- q is an integer of 1 to 10.
- the polythiol compound may be a compound other than the polythiol compound (a) containing a hydrocarbon structure described above, the polythiol compound (b) containing an ether structure, and the polythiol compound (c) containing an ester structure.
- the polythiol compounds include phthalic acid di (1-mercaptoethyl ester), phthalic acid di (2-mercaptopropyl ester), phthalic acid di (3-mercaptobutyl ester), and phthalic acid di (3-mercaptoisobutyl ester). Etc. may be used.
- Preferred polythiol compounds include compounds having a secondary mercapto group, ie, secondary thiol compounds.
- the secondary thiol compound is superior in its storage stability to the primary thiol compound.
- generated using the photocurable sealing material of this embodiment has the sealing characteristic superior to the conventionally known photocurable sealing material.
- the photocurable sealing material of the present embodiment is excellent in coating stability upon application and stability of sealing characteristics. In particular, excellent properties with regard to hardness and flexibility can be obtained stably. The reason is that, for example, due to steric hindrance around the mercapto group, it is presumed that the balance between the radical reaction and the thermal addition reaction in the ene-thiol reaction is preferably adjusted.
- the amount of the polythiol compound used is the total number of (meth) acryloyl groups contained in both the second component (oligomer having a (meth) acryloyl group) and the third component (monomer having a (meth) acryloyl group) described later
- the ratio to the total number of mercapto groups in the first component is 100: 5 n to 100: 25 n (n is the number of mercapto groups in one molecule of the polythiol compound).
- the amount is preferably such that the ratio is 100: 7 n to 100: 20 n, and more preferably the amount is such that the ratio is 100: 9 n to 100: 17 n.
- the above photocurable sealing material is In addition to the above first component, it comprises a second component and a third component, and further comprises a fourth component and / or a fifth component,
- the second component is an oligomer having a (meth) acryloyl group having a weight average molecular weight of 1,000 to 30,000
- the third component is a monomer having a (meth) acryloyl group
- the fourth component is a photo radical polymerization initiator
- the fifth component is a viscosity modifier, 5 to 100 parts by mass of the third component with respect to 100 parts by mass of the second component,
- the ratio of the total number of (meth) acryloyl groups contained in both the second component and the third component to the total number of mercapto groups in the first component is preferably 100: 5 n to 100: 25 n.
- n is the number of mercapto groups in one molecule of the polythiol compound.
- (meth) acryloyl group means an acryloyl group or a methacryloyl group as commonly used in the relevant technical field.
- the photocurable sealing material preferably further comprises a carbodiimide compound as a sixth component in an amount of 0.1 to 15 parts by mass with respect to 100 parts by mass of the second component.
- a carbodiimide compound as a sixth component in an amount of 0.1 to 15 parts by mass with respect to 100 parts by mass of the second component.
- the weight average molecular weight of the second component oligomer is preferably 1000 to 30000, more preferably 2000 to 25000, still more preferably 3000 to 25000, still more preferably 4000 to 22000, and particularly preferably It is 5000 to 18000.
- the weight average molecular weight can be measured, for example, by gel permeation chromatography (GPC).
- the second component oligomer is preferably an oligomer having at least two (meth) acrylate groups in the molecule.
- the number of (meth) acrylate groups in one molecule of the oligomer of the second component is, for example, 2 to 10, preferably 2 to 6, more preferably 2 to 4, particularly preferably 2 Is one.
- (meth) acrylate group means an acrylate group or a methacrylate group as commonly used in the art.
- Examples of the second component oligomer include urethane (meth) acrylate oligomers, polyester (meth) acrylate oligomers, polyether (meth) acrylate oligomers, (meth) acrylic (meth) acrylate oligomers, epoxy (meth) Examples thereof include acrylate oligomers, conjugated diene polymer-based (meth) acrylate oligomers such as polybutadiene oligomers, and silicone (meth) acrylate oligomers, and hydrogenated products thereof.
- a urethane type (meth) acrylate oligomer means the (meth) acrylate oligomer containing a urethane bond.
- a polyurethane oligomer is obtained by reacting a polyol such as polyether polyol, polyester polyol, carbonate diol and the like with a polyisocyanate to obtain a polyurethane oligomer, and the polyurethane oligomer is converted to (meth) acrylic acid And oligomers obtained by esterification with
- (meth) acrylic acid means acrylic acid or methacrylic acid as commonly used in the art.
- the polyester-based (meth) acrylate oligomer means a (meth) acrylate oligomer containing an ester bond.
- polyester-based (meth) acrylate oligomers for example, polyester oligomers having hydroxyl groups at both ends are obtained by condensing polyvalent carboxylic acid and polyvalent alcohol or adding polyvalent carboxylic acid alkylene oxide. And oligomers obtained by esterifying the hydroxyl group with (meth) acrylic acid.
- the polyether based (meth) acrylate oligomer means a (meth) acrylate oligomer containing an ether bond.
- a polyether type (meth) acrylate oligomer the oligomer obtained by esterifying the hydroxyl group of polyether polyol with (meth) acrylic acid is mentioned, for example.
- (meth) acrylic (meth) acrylate oligomer examples include telechelic polyacrylates whose structure is highly controlled by application of atom transfer radical polymerization (ATRP) method.
- ATRP atom transfer radical polymerization
- (meth) acrylic means acrylic or methacrylic as commonly used in the art.
- An epoxy type (meth) acrylate oligomer means the (meth) acrylate oligomer containing an epoxy group.
- an epoxy type (meth) acrylate oligomer for example, an oligomer obtained by reacting and esterifying (meth) acrylic acid with an oxirane ring of a bisphenol type epoxy resin having a relatively low weight average molecular weight and a novolac type epoxy resin Can be mentioned.
- the epoxy-based (meth) acrylate oligomer also includes a carboxyl-modified epoxy acrylate oligomer in which the epoxy-based (meth) acrylate oligomer is partially modified with a dicarboxylic acid anhydride.
- the conjugated diene polymer system (meth) acrylate oligomer means an oligomer obtained by esterifying a conjugated diene polymer with (meth) acrylic acid.
- conjugated diene polymer-based (meth) acrylate oligomers include SBR diacrylate obtained by esterifying liquid styrene-butadiene copolymer with acrylic acid, polyisoprene diacrylate obtained by esterifying polyisoprene with acrylic acid, Examples thereof include polybutadiene acrylate obtained by esterifying polybutadiene with acrylic acid, and polybutadiene acrylate obtained by reacting a (meth) acrylate having an isocyanate group with 1,2-polybutadiene having a hydroxyl group at a molecular terminal.
- the silicone (meth) acrylate oligomer means a (meth) acrylate oligomer containing a siloxane bond.
- a silicone (meth) acrylate oligomer the ester compound of the hydroxyl group of an alcoholic siloxane compound, and acrylic acid etc. are mentioned.
- the oligomers of the second component may be used alone or in combination of two or more.
- a urethane type (meth) acrylate oligomer is mentioned,
- a urethane type polyester (meth) acrylate oligomer is mentioned.
- the urethane-based polyester (meth) acrylate oligomer is obtained by reacting a polyether polyol and a polyisocyanate to obtain a polyurethane oligomer, and esterifying the polyurethane oligomer with (meth) acrylic acid.
- a urethane type (meth) acrylate oligomer having two (meth) acryloyl groups which is a preferable second component oligomer
- polyether diol having two hydroxyl groups, polyester diol and carbonate used for the preparation thereof examples include the following.
- polyether diols examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol and 1,3-butylene glycol, 1,4-butylene glycol, neopentyl glycol, cyclohexane dimethanol, 2, 2- Examples thereof include polyether diols in which ethylene oxide or propylene oxide is added to bis (4-hydroxycyclohexyl) propane, bisphenol A or the like.
- polyester diols examples include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 1,6-hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol A compound in which ethylene oxide or propylene oxide or the like is added to 2,2-bis (4-hydroxycyclohexyl) propane, bisphenol A or the like, or an alcohol in which ⁇ -caprolactone is added, adipic acid, sebacic acid, azelaic acid, The polyester diol etc. which are obtained by making it react with dicarboxylic acids or anhydrides, such as dodecane dicarboxylic acid, etc. are mentioned.
- carbonate diols examples include diaryl carbonates such as diphenyl carbonate, bis-chlorophenyl carbonate, dinaphthyl carbonate, phenyl-toluyl-carbonate, phenyl-chlorophenyl-carbonate, 2-tolyl-4-tolyl carbonate, dimethyl carbonate, diethyl carbonate and the like
- dialkyl carbonates 1,6-hexanediol, neopentyl glycol, 1,4-butanediol, 1,8-octanediol, 1,4-cyclohexanedimethanol, 2-methylpropanediol, dipropylene glycol,
- the carbonate diol etc. which are obtained by reaction with diols, such as dibutylene glycol, etc. are mentioned.
- ⁇ Third component monomer having (meth) acryloyl group>
- Examples of the monomer having a (meth) acryloyl group in the present embodiment include (meth) acrylate monomers and (meth) acrylamide monomers. The details will be described below.
- (Meth) Acrylate Monomer examples include (meth) acrylate monomers having at least one (meth) acryloyl group in the molecule. Specifically, monofunctional monomers having one (meth) acryloyl group, bifunctional monomers having two, trifunctional monomers having three, tetrafunctional monomers having four, and the like can be mentioned.
- the (meth) acrylate monomer may be a (meth) acrylate monomer having at least one polar group selected from the group consisting of a hydroxyl group, a carboxyl group and an amino group.
- monofunctional monomers include methyl methacrylate, butyl methacrylate, 2-phenoxyethyl acrylate, ethoxylated 2-phenoxyethyl acrylate, 2- (2-ethoxyethoxy) ethyl acrylate, EO-modified phenol acrylate, cyclic trimethylolpropane, Formal acrylic acid, ⁇ -carboxyethyl acrylate, lauryl methacrylate, isooctyl acrylate, stearyl methacrylate, isodecyl acrylate, isostearyl acrylate, isobornyl methacrylate, benzyl acrylate, hydroxypivalyl hydroxypivalate diacrylate, ethoxylated 1,6-hexanediol diacrylate, dipropylene glycol diacrylate, tricyclodecane dime Nole diacrylate, ethoxylated dipropylene glycol diacrylate, neopen
- difunctional monomers examples include 1,6-hexanediol diacrylate, bisphenol A ethoxylated acrylate, polyethylene glycol diacrylate (200-600), tripropylene glycol diacrylate, neopentyl glycol propoxylate (2), and ethoxylated (2) Neopentyl glycol diacrylate, dipropylene glycol diacrylate, trimethylolpropane ethoxylated (3) methyl ether diacrylate, and combinations of two or more of these.
- trifunctional monomers examples include trimethylolpropane triacrylate, trimethylolpropane propoxylated (5-20) triacrylate, propoxylated (4) glycerol triacrylate, ethoxylated (3) trimethylolpropane triacrylate, propoxy And fluorinated pentaerythritol triacrylate, and combinations of two or more thereof.
- tetrafunctional monomers include ditrimethylolpropane tetraacrylate, dipentaerythritol mono-hydroxypentaacrylate, and combinations of two or more thereof.
- a (meth) acrylate monomer may be used individually by 1 type, it can also be used in combination of 2 or more types.
- Preferred (meth) acrylate monomers include monofunctional monomers.
- As the (meth) acrylate monomer a combination of a monofunctional monomer and a difunctional monomer is also preferable. More preferred are monofunctional monomers.
- (Meth) Acrylamide Monomer The above (meth) acrylamide monomer is CH 2 CXCX (CO) NR 2 (X is a hydrogen atom or a methyl group, and R may be each independently a linear substituent, And (2) a (meth) acrylamide monomer represented by (2) may be a cyclic substituent in which two R's are taken together).
- (meth) acrylamide monomer is meant an acrylamide monomer or methacrylamide monomer, as commonly used in the art.
- the (meth) acryloyl morpholine monomer represented by following formula (15), a dimethyl acrylamide monomer, etc. are mentioned, for example.
- X represents a hydrogen atom or methyl.
- the (meth) acrylamide monomer preferably comprises (meth) acryloyl morpholine monomer.
- the (meth) acryloyl morpholine monomer comprises acryloyl morpholine monomer.
- the amount of the (meth) acryloyl group-containing monomer used is preferably in the range of 5 to 100 parts by mass with respect to 100 parts by mass of the second component (meth) acryloyl group-containing oligomer. By using the amount in this range, the viscosity of the photocurable sealing material of this embodiment can be reduced, and the flexibility of the photocurable sealing material can be further improved.
- the use amount of the monomer having a (meth) acryloyl group is more preferably in the range of 10 to 80 parts by mass, still more preferably 40 to 70 parts by mass with respect to 100 parts by mass of the second component. .
- the type and amount of use of the (meth) acryloyl group-containing monomer can be appropriately adjusted in order to obtain properties such as viscosity and flexibility. .
- radical photopolymerization initiator for example, an intramolecular cleavage type and / or a hydrogen abstraction type photo radical polymerization initiator can be used.
- an intramolecular cleavage type photoradical polymerization initiator is mentioned.
- the radical UV polymerization initiator known ones can be suitably used.
- benzoins such as benzoin, benzoin methyl ether and benzoin ethyl ether and alkyl ethers thereof: acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 4- (1- (1-) Acetophenones such as t-butyldioxy-1-methylethyl) acetophenone and diethoxyacetophenone; anthraquinones such as 2-methyl anthraquinone, 2-amyl anthraquinone, 2-t-butyl anthraquinone and 1-chloroanthraquinone; 2,4-dimethyl Thioxanthones such as thioxanthone, 2,4-diisopropylthioxanthone and 2-chlorothioxanthone; Ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophene
- Preferred photo radical polymerization initiators include benzoins, ketals, ⁇ -hydroxyalkyl phenones, ⁇ -aminoalkyl phenones, acyl phosphine oxides, phenylglyoxylates, acetophenones, and titanocene compounds.
- a cleavage type photo radical initiator is mentioned.
- the addition amount of the photo radical polymerization initiator is not particularly limited, and examples thereof include 0.1 to 10 parts by mass with respect to 100 parts by mass of the total of the first to third components.
- the addition amount is preferably 0.2 to 5 parts by mass, and more preferably 0.5 to 2 parts by mass with respect to 100 parts by mass of the total of the first to third components.
- the viscosity modifier is not particularly limited, and, for example, inorganic viscosity modifiers such as white carbon, colloidal silica, silica sand (silica powder), aerosil, diatomaceous earth, hydrophobic calcium carbonate, glass balloon and glass beads And polyvinyl pyrrolidone and the like. These viscosity modifiers may be used alone or in combination of two or more. Preferred viscosity modifiers include inorganic viscosity modifiers.
- the addition amount of the viscosity modifier is not particularly limited, and for example, 0.1 to 20 parts by mass can be mentioned with respect to 100 parts by mass of the total of the first to third components, and preferably 0 And 2 to 10 parts by mass.
- a carbodiimide compound means a compound containing a carbodiimide group.
- the carbodiimide compound acts as a hydrolysis resistant stabilizer (hydrolysis resistant agent) that suppresses a hydrolysis chain by blocking a hydroxyl group or a carboxyl group generated by hydrolysis of a resin such as polyester.
- a hydrolysis resistant stabilizer hydrolysis resistant agent
- a monocarbodiimide compound, a polycarbodiimide compound, etc. are mentioned, generally known widely, and all can be used.
- carbodiimide compounds include, for example, JP-A-09-309871, JP-A-09-249801, JP-A-09-208649, JP-A-09-296097, JP-A-08-081533, JP-A-08- Japanese Patent Application Publication Nos. 0927068, 09-12,3585, 09-188807, 2005-082642, 2005-053870, 2012-036392 Patent Publications: JP-A-2010-163203, JP-A-2011-174094, International Publication No. 2008/072514, JP-A-2012-081759, JP-A-2012-052014, JP-A-2012-007079, etc. The compound described in is mentioned.
- each of R 11 in the repeating unit is the same or different and is a divalent aromatic group and / or an aliphatic group.
- r is a natural number.
- R 11 may also be substituted by aliphatic and / or alicyclic and / or aromatic substituents having at least one carbon atom. Good. Here, these substituents may have a hetero atom. Also, these substituents may be substituted at at least one ortho position of the aromatic group to which the carbodiimide group is bonded.
- R 12 is C 1 to C 18 alkyl, C 5 to C 18 cycloalkyl, aryl, C 7 to C 18 aralkyl, -R 11 -NH-COS-R 14 , -R 11 COOR 14 , -R 11 -OR 14, -R 11 -N (R 14 ) 2, -R 11 -SR 14, -R 11 -OH, -R 11 -NH 2, -R 11 -NHR 14, -R 11 - epoxy, -R 11 - NCO, -R 11 -NHCONHR 14 , -R 11 -NHCONR 14 R 15 or -R 11 -NHCOOR 16
- R 14 and R 15 are identical or different, C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 7 -C 18 aralkyl, oligo / polyethylene glycols and / or oligo / polypropylene glycol It is kind.
- R 16 is a substituent defined as the substituent of R 14 above, or is a polyester group or a polyamide group.
- r is an integer of 1 to 5.
- r is an integer greater than 5.
- the amount of the carbodiimide compound used is, for example, in the range of 0.1 to 15 parts by mass with respect to 100 parts by mass of the (meth) acryloyl group-containing oligomer which is the second component.
- the above-mentioned usage fee is preferably 0.5 to 12 parts by mass, more preferably 1 to 10 parts by mass, with respect to 100 parts by mass of the (meth) acryloyl group-containing oligomer which is the second component. .
- the carbodiimide compound When the carbodiimide compound is added to the photocurable sealing material according to the present embodiment, it is stable for 6 months or more and has excellent storage stability. In addition, there is almost no adverse effect on the properties of the light curing property and the sealing material produced by light curing.
- the present inventors estimate that the effect of storage stabilization by the carbodiimide compound is produced by the following mechanism.
- the ene-thiol-based photocurable resin material is degraded in quality because the reaction between the active mercapto group contained therein and the double bond proceeds during storage to gelate.
- the carbodiimide compound when the carbodiimide compound is contained in the resin material, the carbodiimide compound preferentially bonds to and deactivates the most active mercapto group, so that the deterioration of quality due to gelation is suppressed, and the storage stabilization effect is It is happening.
- the carbodiimide compounds described above can also be used as stabilizers for ene-thiol photocurable resin materials.
- the amount of the carbodiimide compound to be added to the ene-thiol photocurable resin material can be appropriately changed and used.
- the photocurable sealing material according to the present embodiment can also have a sensitizer added so that it can be photocured using visible light and near infrared rays as well as ultraviolet light.
- sensitizers include unsaturated ketones such as chalcone derivatives and dibenzalacetone, 1,2-diketone derivatives such as camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene Derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, polymethine pigments such as merocyanine derivatives, merocyanine derivatives and oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives,
- the addition amount of the sensitizer is not particularly limited, and may be, for example, 0.1 to 10 parts by mass with respect to 100 parts by mass of the total of the first to third components.
- the addition amount is preferably 0.2 to 5 parts by mass, and more preferably 0.5 to 2 parts by mass with respect to 100 parts by mass of the total of the first to third components.
- ⁇ Other ingredients can be further added to the photocurable sealing material of the present embodiment.
- other components for example, thickeners, polymerization inhibitors, pigments, adhesion improvers, antioxidants, curing accelerators, fillers, plasticizers, surfactants, lubricants, antistatic agents, stabilizers, etc. Can be mentioned. An appropriate amount of these components can be added according to each purpose.
- the Shore 00 hardness of the sheet after photocuring in the photocurable sealing material according to the present embodiment is preferably 5 to 100 in an environment of 23 ° C. and relative humidity 50 to 60% RH. It is more preferably 5 to 90, still more preferably 5 to 85.
- the Shore 00 hardness can be measured, for example, by a method in accordance with ASTM D 2240.
- the photocurable sealing material of the present embodiment is a polythiol compound as the first component, an oligomer having a (meth) acryloyl group having a weight average molecular weight of 1,000 to 30,000 as the second component, and a third component (meta ) Acrylate monomer, Photoradical polymerization initiator as fourth component and / or viscosity modifier as fifth component, and, if necessary, carbodiimide compound as sixth component, sensitizer as seventh component, and It can be prepared by mixing and / or other components using a mixer such as a mixer, a ball mill or a 3-roll mill under room temperature or heating conditions.
- a mixer such as a mixer, a ball mill or a 3-roll mill under room temperature or heating conditions.
- the said photocurable sealing material can also be adjusted by adding and melt
- a solvent used as a diluent for example, esters such as ethyl acetate, butyl acetate and isopropyl acetate, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, cyclic ethers such as tetrahydrofuran and dioxane, N, N-dimethylformamide and the like
- aromatic hydrocarbons such as toluene, halogenated hydrocarbons such as methylene chloride, and the like.
- Method of applying light curable sealing material Although it does not restrict
- energy rays used include electromagnetic waves such as light, radiation and the like. Specifically, ultraviolet light, visible light, infrared light, ⁇ rays, ⁇ rays, ⁇ rays, electron beams and the like can be mentioned. From the viewpoint of operability, productivity and economy, it is preferable to use ultraviolet light.
- the irradiation time of the energy beam can be appropriately selected according to the type of energy beam to be used.
- an ultraviolet light source for example, a light source such as ultra-high pressure mercury, a metal halide light source, a laser, and an LED can be used.
- a light source such as ultra-high pressure mercury, a metal halide light source, a laser, and an LED
- curing can be proceeded promptly without containing a photo radical polymerization initiator, but in the case of using ultraviolet light, photo radical polymerization
- an initiator is added to the photocurable sealing material of this embodiment.
- the housing of the present embodiment can be manufactured according to the following steps (1) to (4).
- the “casing” refers to a machine, an electrical device, and a box having these functions accommodated therein, and the device includes impact, pressure, electromagnetic waves, water, dust, light, etc. Means something to protect from.
- the machines and electric devices include electronic products such as mobile phones, digital cameras and video cameras, household appliances such as refrigerators, air conditioners and washing machines, and precision devices such as cameras and watches.
- the photocurable sealing material of the present embodiment has high self-adhesiveness, and thereby has excellent sealing properties. Further, the photocurable sealing material can be automatically coated by a robot on a housing without using a mold. Therefore, the said photocurable sealing material is excellent in operativity and mass-productivity compared with the conventional sealing material.
- Examples 2 to 8 and Comparative Example 1 The photocurable sealing materials of Examples 2 to 8 and the photocurable sealing materials of Comparative Example 1 were prepared in the same manner as in Example 1 except that each raw material was used in the composition described in Table 1. Obtained.
- the Shore 00 hardness of the sample produced as described above was measured and evaluated by the following method. According to ASTM D 2240, a plurality of cured product sheets having a thickness of about 1 mm of each photocurable sealing material were laminated to a thickness of about 6 mm or more to obtain a specimen. Thereafter, the Shore 00 hardness of the sample obtained was measured with a type 00 durometer (trade name: GS-754G, manufactured by Techlock Co., Ltd.) under an environment of 23 ° C. and a relative humidity of 50 to 60% RH. The evaluation results are shown in Table 1.
- FIG. 1 is a schematic top cross-sectional view for explaining the configuration of a waterproofness evaluation sample 10.
- FIG. 2 is a side cross-sectional schematic view for explaining the configuration of the waterproofness evaluation sample 10. The preparation of the waterproof evaluation sample 10 will be described with reference to FIGS. 1 and 2.
- Each of the photocurable sealing materials 1a obtained in Example 1 and Comparative Example 1 is line-coated in a square (line width, height 2 mm, 30 mm square) on a polycarbonate plate 2 (1 mm thick, 100 mm square) Then, using an electrodeless metal halide lamp type UV irradiation device (Light Hammer 6 manufactured by Heraeus), curing was carried out by UV irradiation (integrated light quantity of UV-A wave: about 6000 mJ / cm 2 ) (FIG. 1). Two pieces of each of the photocurable sealing materials 1a of Example 1 and Comparative Example 1 were produced (hereinafter, these are referred to as "substrate A" and "substrate B").
- the integrated light quantity was measured with a luminometer (UV Power Puck manufactured by Heraeus).
- a luminometer UV Power Puck manufactured by Heraeus
- cobalt chloride paper 3 was placed inside a square frame made of the light-cured sealing material 1 b on the substrate A as an index for confirming the penetration of water (FIG. 1).
- the cable 4 (0.5 mm in diameter, 150 mm in length) was placed over the photocured sealing material 1 b on the substrate A.
- the spacer 5 (2 mm thickness) was arrange
- the substrate B was superimposed on the substrate A so that the surfaces coated with the light-cured sealing material 1b face each other, and were clamped and fixed by the clamp 6 (FIG. 2). Thereafter, the photocured sealing material 1b of the substrate A and the substrate B is compressed by 50% to obtain a waterproofness evaluation specimen 10 (FIG. 1, FIG. 2).
- the self-adhesive photocurable sealing material is excellent in waterproofness.
- 1a Photo-curable sealing material 1b Photo-cured sealing material, 2 Polycarbonate board, 3 Cobalt chloride paper, 4 cables, 5 spacers, 6 clamps, 10 Water resistance test specimens.
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Abstract
Description
耐熱性及び防水性等が不充分であること、
湿気混入の防止等の操作性が煩雑であること、
加熱の為の装置が必要になること、
筐体の熱的損傷が懸念されること、
金型を用いる製造の操作性が煩雑であること、
等の課題があり、電子部品、家電製品、精密機器などの筐体に、充分に満足できるシーリング特性を付与できるものはなく、その提供が所望されている。
[1]第1成分としてポリチオール化合物を少なくとも含む光硬化性シーリング用材料であって、
上記光硬化性シーリング用材料を用いて厚さ1mm、幅25mm、長さ200mmの2枚のシートを作製し、紫外線を照射して光硬化させた後上記2枚のシートを積層して10kgの荷重を10秒間負荷させた場合、上記2枚のシートの積層界面が消失する作用を示し、かつ、T型剥離試験における自着強度が剥離速度300mm/minにて引張したとき5N/25mm以上である、光硬化性シーリング用材料。
[2]上記自着強度は、剥離速度300mm/minにて引張したとき1000N/25mm以下である、[1]に記載の光硬化性シーリング用材料。
[3]光硬化させた後の上記シートのショア00硬度は、23℃、相対湿度50~60%RHの環境下で5~100である、[1]又は[2]に記載の光硬化性シーリング用材料。
[4]上記第1成分に加えて、第2成分及び第3成分を含み、且つ
第4成分及び/又は第5成分を更に含み、
上記第2成分は、重量平均分子量が1000~30000である(メタ)アクリロイル基を有するオリゴマーであり、
上記第3成分は、(メタ)アクリロイル基を有するモノマーであり、
上記第4成分は、光ラジカル重合開始剤であり、
上記第5成分は、粘性調整剤であり、
上記第2成分100質量部に対して、上記第3成分を5~100質量部含み、
上記第2成分及び上記第3成分の双方に含まれる(メタ)アクリロイル基の総数と、上記第1成分におけるメルカプト基の総数との比が、100:5n~100:25n(nは、上記ポリチオール化合物1分子中のメルカプト基の数である。)である、[1]~[3]のいずれかに記載の光硬化性シーリング用材料。
[5]上記第2成分は、ウレタン系(メタ)アクリレートオリゴマー、ポリエステル系(メタ)アクリレートオリゴマー、ポリエーテル系(メタ)アクリレートオリゴマー、(メタ)アクリル(メタ)アクリレートオリゴマー、エポキシ系(メタ)アクリレートオリゴマー、共役ジエン重合体系(メタ)アクリレートオリゴマー及びシリコーン(メタ)アクリレートオリゴマー、並びに、それらの水素添加物を含む群から選択される少なくとも1種を含む、[4]に記載の光硬化性シーリング用材料。
[6]さらに、第6成分としてカルボジイミド化合物を、上記第2成分100質量部に対して0.1~15質量部含む、[4]又は[5]に記載の光硬化性シーリング用材料。
本実施形態に係る光硬化性シーリング用材料は、第1成分としてポリチオール化合物を少なくとも含む光硬化性シーリング用材料であって、上記光硬化性シーリング用材料を用いて厚さ1mm、幅25mm、長さ200mmの2枚のシートを作製し、紫外線を照射して光硬化させた後上記2枚のシートを積層して10kgの荷重を10秒間負荷させた場合、上記2枚のシートの積層界面が消失する作用を示し、かつ、T型剥離試験における自着強度が剥離速度300mm/minにて引張したとき5N/25mm以上である、光硬化性シーリング用材料である。上記光硬化性シーリング材料は、このような構成を備えることによって、所定の自着性を示し、気密性及び防水性が優れているという効果を奏する。以下、気密性及び防水性をまとめて「シーリング特性」という場合がある。
第1成分であるポリチオール化合物は、2以上のメルカプト基を有する化合物を意味する。上記ポリチオール化合物としては、例えば、分子内にメルカプト基を2~10個有するポリチオール化合物が挙げられる。好ましくは、分子内にメルカプト基を2~6個有するポリチオール化合物が挙げられる。より好ましくは、分子内にメルカプト基を3~4個有するポリチオール化合物が挙げられる。
(a)炭化水素構造を含むポリチオール化合物(C2-20アルカンポリチオール等の脂肪族ポリチオール類、キシリレンジチオール等の芳香脂肪族ポリチオール類、アルコール類のハロヒドリン付加物のハロゲン原子をメルカプト基で置換してなるポリチオール類、ポリエポキシド化合物の硫化水素反応生成物からなるポリチオール化合物等)、
(b)式(1)で表されるエーテル構造を含むポリチオール化合物、及び
(c)式(2)で表されるエステル構造を含むポリチオール化合物が挙げられる。式(1)及び式(2)において、R1及びR2は独立して水素原子又はC1-10アルキル基を示し、mは、0、1又は2であり、pは、0又は1である。なお、「C2-20」及び「C1-10」との表記は、それぞれ炭素数が2~20及び1~10であることを意味する(以下、同様)。
上記第1成分に加えて、第2成分及び第3成分を含み、且つ
第4成分及び/又は第5成分を更に含み、
上記第2成分は、重量平均分子量が1000~30000である(メタ)アクリロイル基を有するオリゴマーであり、
上記第3成分は、(メタ)アクリロイル基を有するモノマーであり、
上記第4成分は、光ラジカル重合開始剤であり、
上記第5成分は、粘性調整剤であり、
上記第2成分100質量部に対して、上記第3成分を5~100質量部含み、
上記第2成分及び上記第3成分の双方に含まれる(メタ)アクリロイル基の総数と、上記第1成分におけるメルカプト基の総数との比が、100:5n~100:25nであることが好ましい。ここで、nは、上記ポリチオール化合物1分子中のメルカプト基の数である。ここで、「(メタ)アクリロイル基」とは、当該技術分野において常用されているように、アクリロイル基又はメタクリロイル基を意味する。
第2成分のオリゴマーの重量平均分子量は、好ましくは1000~30000であり、より好ましくは2000~25000であり、更に好ましくは3000~25000であり、更により好ましくは4000~22000であり、特に好ましくは5000~18000である。重量平均分子量は、例えば、ゲル浸透クロマトグラフィー(GPC)によって測定することが可能である。第2成分のオリゴマーは、好ましくは、分子内に少なくとも2個の(メタ)アクリレート基を有するオリゴマーが挙げられる。第2成分のオリゴマーの1分子中の(メタ)アクリレート基の個数は、例えば2~10個であり、好ましくは2~6個であり、より好ましくは2~4個であり、特に好ましくは2個である。ここで、「(メタ)アクリレート基」とは、当該技術分野において常用されているように、アクリレート基又はメタクリレート基を意味する。
本実施形態における(メタ)アクリロイル基を有するモノマーは、例えば、(メタ)アクリレートモノマー及び(メタ)アクリルアミドモノマー等が挙げられる。以下、詳細に説明する。
(メタ)アクリレートモノマーとしては、分子内に(メタ)アクリロイル基を少なくとも1個有する(メタ)アクリレートモノマーが挙げられる。具体的には、(メタ)アクリロイル基を1個有する単官能モノマー、2個有する二官能モノマー、3個有する三官能モノマー、4個有する四官能モノマー等が挙げられる。また、上記(メタ)アクリレートモノマーは、ヒドロキシル基、カルボキシル基及びアミノ基からなる群から選ばれる少なくとも1つの極性基を有する(メタ)アクリレートモノマーであってもよい。
上記(メタ)アクリルアミドモノマーは、CH2=CX(CO)NR2(Xは水素原子、又はメチル基を示し、Rは、それぞれ独立に直鎖状の置換基でもよいし、2つのRが一緒になった環状の置換基であってもよい。)で表される(メタ)アクリルアミドモノマーを含む。「(メタ)アクリルアミドモノマー」とは、当該技術分野において常用されているように、アクリルアミドモノマー又はメタクリルアミドモノマーを意味する。上記(メタ)アクリルアミドモノマーとしては、例えば、下記式(15)で表される(メタ)アクリロイルモルホリンモノマー、ジメチルアクリルアミドモノマー等が挙げられる。式(15)において、Xは水素原子、又はメチルを示す。上記(メタ)アクリルアミドモノマーは、好ましくは、(メタ)アクリロイルモルホリンモノマーを含む。好ましくは、(メタ)アクリロイルモルホリンモノマーは、アクリロイルモルホリンモノマーを含む。
光ラジカル重合開始剤としては、例えば、分子内開裂型及び/又は水素引き抜き型の光ラジカル重合開始剤を用いることができる。好ましくは分子内開裂型光ラジカル重合開始剤が挙げられる。ラジカル性の紫外線重合開始剤としては、公知のものを好適に使用できる。具体的には、ベンゾイン、ベンゾインメチルエーテル及びベンゾインエチルエーテル等のベンゾイン類並びにそれらのアルキルエーテル類;アセトフェノン、2,2-ジメトキシ-2-フェニルアセトフェノン、1,1-ジクロロアセトフェノン、4-(1-t-ブチルジオキシ-1-メチルエチル)アセトフェノン及びジエトキシアセトフェノン等のアセトフェノン類;2-メチルアントラキノン、2-アミルアントラキノン、2-t-ブチルアントラキノン及び1-クロロアントラキノン等のアントラキノン類;2,4-ジメチルチオキサントン、2,4-ジイソプロピルチオキサントン及び2-クロロチオキサントン等のチオキサントン類;アセトフェノンジメチルケタール及びベンジルジメチルケタール等のケタール類;ベンゾフェノン、4-(1-t-ブチルジオキシ-1-メチルエチル)ベンゾフェノン及び3,3’,4,4’-テトラキス(t-ブチルジオキシカルボニル)ベンゾフェノン等のベンゾフェノン類;2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノ-プロパン-1-オン及び2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-1-ブタノン等のα-アミノアルキルフェノン類;1-ヒドロキシ-シクロヘキシル-フェニル-ケトン、2-ヒドロキシ-1{4-[4-(2-ヒドロキシ-2-メチル-プロビオニル)-ベンジル]フェニル}-2-メチル-プロパン-1-オン及び2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン等のα-ヒドロキシアルキルフェノン類;アルキルフェニルグリオキシレート等のフェニルグリオキシレート類;ジエトキシアセトフェノン;2,4,6-トリメチルベンゾイルフェニルエトキシホスフィンオキサイド等のアシルホスフィンオキサイド類;ビス(5,2,4-シクロペンタジエン-1-イル)-ビス(2,6-ジフルオロ-3-(1H-ピロール-1-イル)-フェニル)チタニウム等のチタノセン化合物等、並びに、これらの2種以上の組合せが挙げられる。
粘性調整剤としては、特に限定されるものではないが、例えば、ホワイトカーボン、コロイダルシリカ、珪砂(珪石粉)、アエロジル、珪藻土、疎水性炭酸カルシウム、ガラスバルーン及びガラスビーズ等の無機系粘性調整剤、ポリビニルピロリドン等が挙げられる。これらの粘性調整剤は、単独で用いられてもよいし、2種類以上が併用されてもよい。好ましい粘性調整剤としては、無機系粘性調整剤が挙げられる。
カルボジイミド化合物とは、カルボジイミド基を含む化合物を意味する。上記カルボジイミド化合物は、ポリエステル等の樹脂の加水分解によって生じるヒドロキシル基又はカルボキシル基を封鎖することで加水分解の連鎖を抑制する耐加水分解安定剤(耐加水分解剤)として作用する。カルボジイミド化合物としては、モノカルボジイミド化合物及びポリカルボジイミド化合物等が挙げられ、一般に広く知られており、いずれも使用することができる。カルボジイミド化合物は、例えば、特開平09-309871号公報、特開平09-249801号公報、特開平09-208649号公報、特開平09-296097号公報、特開平08-081533号公報、特開平08-027092号公報、特開平09-136869号公報、特開平09-124582号公報、特開平09-188807号公報、特開2005-082642号公報、特開2005-053870号公報、特開2012-036392号公報、特開2010-163203号公報、特開2011-174094号公報、国際公開第2008/072514号、特開2012-081759号公報、特開2012-052014号公報、特開2012-007079号公報等に記載された化合物が挙げられる。
本実施形態に係る光硬化性シーリング用材料は、紫外線のみでなく、可視光及び近赤外線を用いても、光硬化できるように、増感剤を添加することもできる。増感剤としては、例えば、カルコン誘導体及びジベンザルアセトン等の不飽和ケトン類、カンファーキノン等の1,2-ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体及びオキソノ-ル誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、並びに有機ルテニウム錯体等が挙げられる。
本実施形態の光硬化性シーリング用材料には、さらにその他の成分を添加することができる。その他の成分としては、例えば、増粘剤、重合禁止剤、顔料、密着性向上剤、酸化防止剤、硬化促進剤、充填剤、可塑剤、界面活性剤、滑剤、帯電防止剤、安定剤等が挙げられる。これら成分は、それぞれの目的に応じて、適量添加することができる。
本実施形態に係る光硬化性シーリング用材料における、光硬化させた後の上記シートのショア00硬度は、23℃、相対湿度50~60%RHの環境下で5~100であることが好ましく、5~90であることがより好ましく、5~85であることが更に好ましい。上記ショア00硬度がこのような範囲にあることによって、シーリング特性が更に向上する。上記ショア00硬度は、例えば、ASTM D 2240に準拠した方法によって測定できる。
本実施形態の光硬化性シーリング用材料は、第1成分であるポリチオール化合物、第2成分である重量平均分子量が1000~30000である(メタ)アクリロイル基を有するオリゴマー、第3成分である(メタ)アクリレートモノマー、並びに第4成分である光ラジカル重合開始剤及び/又は第5成分である粘性調整剤、並びに必要に応じて第6成分であるカルボジイミド化合物、第7成分である増感剤、及び/又はその他の成分を、室温又は加熱条件下で、ミキサー、ボールミル、3本ロールミル等の混合機を用いて混合することで調製できる。また、上記光硬化性シーリング用材料は、必要に応じて、溶剤などを希釈剤として添加して溶解し、混合することで、調整することもできる。希釈剤として用いる溶剤としては、例えば、酢酸エチル、酢酸ブチル及び酢酸イソプロピル等のエステル、アセトン、メチルエチルケトン、メチルイソブチルケトン及びシクロヘキサノン等のケトン、テトラヒドロフラン及びジオキサン等の環状エーテル、N,N-ジメチルホルムアミド等のアミド、トルエン等の芳香族炭化水素、塩化メチレン等のハロゲン化炭化水素等が挙げられる。
本実施形態の光硬化性シーリング用材料を硬化させる方法としては、特に制限されないが、例えば、エネルギー線を照射することで実施できる。用いられるエネルギー線としては、光等の電磁波、放射線等が挙げられる。具体的には、紫外線、可視光、赤外線、α線、β線、γ線、電子線等が挙げられる。操作性、生産性及び経済性などの観点から、紫外線を用いることが好ましい。エネルギー線の照射時間としては、用いるエネルギー線の種類によって適宜選択することができる。紫外線の光源としては、例えば、超高圧水銀、メタルハライド光源、レーザー、LED等の光源を使用することができる。α線、β線、γ線、電子線等を用いる場合には、光ラジカル重合開始剤を含有させなくても、速やかに硬化を進めることができるが、紫外線を用いる場合には、光ラジカル重合開始剤を本実施形態の光硬化性シーリング用材料に加えることが好ましい。
(1)上記2つの部品それぞれの溝(ガスケット塗付部)に光硬化性シーリング用材料を均一に塗付する;
(2)塗付された上記2つの部品それぞれに紫外線等を照射することで光硬化性シーリング用材料を硬化させてガスケットを生成させる;
(3)必要に応じて内部に収納する機器を組み入れる(例えば、光硬化した上記硬化性シーリング材料を跨ぐように、ケーブル等の「筐体を挿通する部材」を配置し、且つ上記2つの部品において光硬化した上記光硬化性シーリング材料が互いに対向するように、上記2つの部品で挟む等);及び
(4)上記2つの部品を嵌合させる。
本実施形態の光硬化性シーリング用材料は、高い自着性を有し、それによってシーリング特性が優れている。また、上記光硬化性シーリング用材料は、金型を用いずに筐体上でロボットによる自動塗工が可能である。そのため、上記光硬化性シーリング用材料は、従来のシーリング用材料と比べると操作性、量産性に優れる。
光硬化性シーリング用材料の作製には、以下の原料を用いた。
<第1成分>
ポリチオール :カレンズMT PE1(昭和電工株式会社、ペンタエリスリトールテトラキス(3-メルカプトブチレート))
<第2成分>
ウレタンアクリレートA:紫光UV-3000B (日本合成化学工業株式会社、重量平均分子量:18000)
ウレタンアクリレートB:紫光UV-6640B (日本合成化学工業株式会社、重量平均分子量:5000)
<第3成分>
アクリルモノマーA :4-ヒドロキシブチルアクリレート(4-HBA)(大阪有機化学工業株式会社)
アクリルモノマーB :アクリロイルモルホリンモノマー(ACMO)(KJケミカル株式会社)
アクリルモノマーC :ニューフロンティアPHE-2(第一工業製薬株式会社、EO変性フェノールアクリレート)
アクリルモノマーD :イソステアリルアクリレート(大阪有機化学工業)
<第4成分>
光ラジカル重合開始剤 :Irgacure1173(BASFジャパン株式会社、2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン)
<第5成分>
粘性調整剤 :アエロジルRY200(日本アエロジル株式会社、アエロジル)
<第6成分>
カルボジイミド化合物 :エラストスタブH01(日清紡ケミカル株式会社)
<その他の成分>
安定剤 :ハイドロキノン(キシダ化学株式会社)
(光硬化性シーリング用材料の作製)
<実施例1>
ウレタンアクリレートA(日本合成化学工業株式会社製、商品名:紫光UV-3000B)41質量部、ウレタンアクリレートB(日本合成化学工業株式会社製、商品名:紫光UV-6640B)10質量部、アクリルモノマーA(大阪有機化学工業株式会社製、商品名:4-HBA)25質量部、ポリチオールとして分子量544.8のペンタエリトリトールテトラキス(3-メルカプトブチレート)(昭和電工株式会社製、商品名:カレンズMT PE1)18質量部、粘性調整剤(日本アエロジル株式会社製、商品名:アエロジルRY200)7質量部を攪拌機で均一に真空混合した後、光ラジカル重合開始剤として2-ヒドロキシ-2-メチル-1-フェニル-プロパン-1-オン(BASFジャパン株式会社製、商品名:Irgacure1173)1質量部、安定剤として1,4-ベンゼンジオール(キシダ化学株式会社製、商品名:ハイドロキノン)0.05質量部を添加し、攪拌器で均一混合脱泡して、実施例1の光硬化性シーリング用材料を得た。
各原料を表1に記載の組成にて用いたこと以外は、実施例1と同様の方法によって、実施例2~8の光硬化性シーリング用材料及び比較例1の光硬化性シーリング用材料を得た。
<検体の作製>
実施例1~8で得られた光硬化性シーリング用材料及び比較例1で得られた光硬化性シーリング用材料の各々を、厚さ100μmのPETフィルム上で1mm厚のシート状に成形した。その後、無電極メタルハライドランプ式UV照射装置(ヘレウス社製、商品名:Light Hammer 6)を用いて、得られたシートにUV照射して硬化させた(UV-A波の積算光量:約6000mJ/cm2)。硬化させたシートを幅25mm、長さ200mmに切り、裁断されたシートの主面同士を重ねて、10kg荷重を10秒間かけて検体とした。UV照射における積算光量は、ヘレウス社製UV Power Puckにて測定した。
10kg荷重を10秒間かけた直後に上記検体におけるT型剥離強度(自着強度)を引張試験機(オリエンテック社製(現A&D社)、商品名:RTC-1310A)にて測定した。その際に併せて、ANMO Electronics社製デジタルマイクロスコープ(倍率50倍)を用いて2枚のシートの積層界面の有無を確認した。なお、試験温度23℃、剥離速度300mm/minで試験を行った。結果を表1に示す。
上述のように作製した検体におけるショア00硬度を以下の方法で測定して、評価した。ASTM D 2240に準拠し、各光硬化性シーリング材料の厚さが約1mmの硬化物シートを、厚さが約6mm以上になるように複数枚積層して検体とした。その後、23℃、相対湿度50~60%RHの環境下でタイプ00デュロメーター(テクロック社製、商品名:GS-754G)にて得られた検体のショア00硬度を測定した。評価結果を表1に示す。
実施例1と比較例1の光硬化性シーリング用材料を用いて、以下の手順にて防水性の試験を行った。
図1は、防水性評価用検体10の構成を説明する上断面模式図である。図2は、防水性評価用検体10の構成を説明する側面断面模式図である。防水性評価用検体10の作製について、図1及び図2を用いて説明する。実施例1及び比較例1で得られた光硬化性シーリング材料1aの各々を、ポリカーボネート板2(1mm厚、100mm角)上に四角形に線塗布(線幅、高さ共に2mm、30mm角)し、無電極メタルハライドランプ式UV照射装置(ヘレウス社製Light Hammer 6)を用いて、UV照射(UV-A波の積算光量:約6000mJ/cm2)して硬化させた(図1)。実施例1及び比較例1それぞれの光硬化性シーリング材1aについて、各2枚作製した(以下、これらを「基板A」、「基板B」と言う。)。積算光量は、照度計(ヘレウス社製UV Power Puck)にて測定した。次に、水の浸入を確認するための指標として塩化コバルト紙3を、基板Aにおける光硬化したシーリング材1bで作った四角形の枠の内側に置いた(図1)。さらにケーブル4(0.5mmΦ、長さ150mm)を基板Aにおける光硬化したシーリング材1b上に跨ぐように配置した。次いで、スペーサー5(2mm厚)を基板Aにおける光硬化したシーリング材1bで作った四角形の枠の外側に2か所配置した。基板Bを、光硬化したシーリング材1bを塗布した面が互いに向き合うように、基板Aに重ねて、クランプ6で挟み込んで固定した(図2)。その後、基板A及び基板Bにおける光硬化したシーリング材1bを50%圧縮して、防水性評価用検体10とした(図1、図2)。
検体を水が入った防水試験機(ハムロンテック社製、商品名:水没気密試験器 HPT8701P01)内に入れ、所定の圧力で加圧し、2分以内に光硬化性シーリング材料の四角形の枠の内部に水が浸入するか否かについて、塩化コバルト紙の色の変化を指標に観測した。すなわち、塩化コバルト紙の色が青色のままであった場合、防水試験に合格したと判断し、塩化コバルト紙の色が青色から赤色に変化していた場合、防水試験は不合格であったと判断した。結果を表2に示す。
Claims (6)
- 第1成分としてポリチオール化合物を少なくとも含む光硬化性シーリング用材料であって、
前記光硬化性シーリング用材料を用いて厚さ1mm、幅25mm、長さ200mmの2枚のシートを作製し、紫外線を照射して光硬化させた後前記2枚のシートを積層して10kgの荷重を10秒間負荷させた場合、前記2枚のシートの積層界面が消失する作用を示し、かつ、T型剥離試験における自着強度が剥離速度300mm/minにて引張したとき5N/25mm以上である、光硬化性シーリング用材料。 - 前記自着強度は、剥離速度300mm/minにて引張したとき1000N/25mm以下である、請求項1に記載の光硬化性シーリング用材料。
- 光硬化させた後の前記シートのショア00硬度は、23℃、相対湿度50~60%RHの環境下で5~100である、請求項1又は請求項2に記載の光硬化性シーリング用材料。
- 前記第1成分に加えて、第2成分及び第3成分を含み、且つ
第4成分及び/又は第5成分を更に含み、
前記第2成分は、重量平均分子量が1000~30000である(メタ)アクリロイル基を有するオリゴマーであり、
前記第3成分は、(メタ)アクリロイル基を有するモノマーであり、
前記第4成分は、光ラジカル重合開始剤であり、
前記第5成分は、粘性調整剤であり、
前記第2成分100質量部に対して、前記第3成分を5~100質量部含み、
前記第2成分及び前記第3成分の双方に含まれる(メタ)アクリロイル基の総数と、前記第1成分におけるメルカプト基の総数との比が、100:5n~100:25n(nは、前記ポリチオール化合物1分子中のメルカプト基の数である。)である、請求項1~請求項3のいずれか一項に記載の光硬化性シーリング用材料。 - 前記第2成分は、ウレタン系(メタ)アクリレートオリゴマー、ポリエステル系(メタ)アクリレートオリゴマー、ポリエーテル系(メタ)アクリレートオリゴマー、(メタ)アクリル(メタ)アクリレートオリゴマー、エポキシ系(メタ)アクリレートオリゴマー、共役ジエン重合体系(メタ)アクリレートオリゴマー、及びシリコーン(メタ)アクリレートオリゴマー、並びに、それらの水素添加物を含む群から選択される少なくとも1種を含む、請求項4に記載の光硬化性シーリング用材料。
- さらに、第6成分としてカルボジイミド化合物を、前記第2成分100質量部に対して0.1~15質量部含む、請求項4又は請求項5に記載の光硬化性シーリング用材料。
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EP3744807A1 (en) | 2020-12-02 |
EP3744807A4 (en) | 2021-10-20 |
KR20200111199A (ko) | 2020-09-28 |
CN111699234A (zh) | 2020-09-22 |
TWI712681B (zh) | 2020-12-11 |
US20210054251A1 (en) | 2021-02-25 |
JPWO2019146421A1 (ja) | 2021-02-04 |
US11130891B2 (en) | 2021-09-28 |
TW201936875A (zh) | 2019-09-16 |
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