CN116057093A - Resin composition for photocurable backing material, and cured product thereof - Google Patents
Resin composition for photocurable backing material, and cured product thereof Download PDFInfo
- Publication number
- CN116057093A CN116057093A CN202180062222.4A CN202180062222A CN116057093A CN 116057093 A CN116057093 A CN 116057093A CN 202180062222 A CN202180062222 A CN 202180062222A CN 116057093 A CN116057093 A CN 116057093A
- Authority
- CN
- China
- Prior art keywords
- meth
- acrylate
- photocurable
- backing material
- resin composition
- 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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- 239000000463 material Substances 0.000 title claims abstract description 47
- 239000011342 resin composition Substances 0.000 title claims abstract description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 58
- 239000004593 Epoxy Substances 0.000 claims abstract description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 22
- 239000002562 thickening agent Substances 0.000 claims abstract description 16
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims description 25
- -1 a1/a2 Chemical compound 0.000 claims description 19
- 239000003365 glass fiber Substances 0.000 claims description 9
- 230000002787 reinforcement Effects 0.000 claims description 6
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000008719 thickening Effects 0.000 abstract description 10
- 238000005452 bending Methods 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003822 epoxy resin Substances 0.000 description 17
- 229920000647 polyepoxide Polymers 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 11
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 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 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229920006337 unsaturated polyester resin Polymers 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 2
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- WTKWFNIIIXNTDO-UHFFFAOYSA-N 3-isocyanato-5-methyl-2-(trifluoromethyl)furan Chemical compound CC1=CC(N=C=O)=C(C(F)(F)F)O1 WTKWFNIIIXNTDO-UHFFFAOYSA-N 0.000 description 1
- DYBDHAUFDFRVNL-UHFFFAOYSA-N 3-methyl-4-[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl]-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical class C1C2OC2CC(C)C1(C(O)=O)CC1CC2OC2CC1C DYBDHAUFDFRVNL-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- RYDWCUQXRZTKLZ-UHFFFAOYSA-N 4-hydroxy-2,3-bis(oxiran-2-ylmethyl)benzoic acid Chemical compound C1OC1CC=1C(C(=O)O)=CC=C(O)C=1CC1CO1 RYDWCUQXRZTKLZ-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- IDLJKTNBZKSHIY-UHFFFAOYSA-N [4-(diethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1 IDLJKTNBZKSHIY-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- IZJDCINIYIMFGX-UHFFFAOYSA-N benzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=CC2=C1 IZJDCINIYIMFGX-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N n-Dodecanedioic acid Natural products OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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
- C08F2/44—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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Provided is a resin composition for a photocurable backing material, which is characterized by comprising: a resin component (A) containing an epoxy (meth) acrylate (a 1) having a carboxyl group and an unsaturated monomer (a 2) as essential components, a thickener (B) and a photopolymerization initiator (C). The resin composition for a photocurable lining material exhibits suitable thickening behavior and excellent curability, and can give a cured product of the lining material excellent in bending strength, tensile elongation and heat resistance, and therefore can be suitably used for pipe repair of sewer pipes and the like.
Description
Technical Field
The present invention relates to a resin composition for a photocurable backing material, and a cured product thereof.
Background
As a repair method of an aged pipe such as a sewer pipe, a thermosetting repair method using a lining material using a styrene-based unsaturated polyester resin composition and a vinyl ester resin composition is often used, but these materials require a reduction in the construction time.
Under such circumstances, a curable resin composition comprising an unsaturated polyester having a number average molecular weight in the range of 500 to 4000 and a monofunctional (meth) acrylate monomer having, as an alcohol residue, a group containing a cyclic hydrocarbon group having 1 carbon-carbon double bond or nitrogen atom in the ring has been proposed (for example, refer to patent document 1). However, it is difficult to achieve both toughness and heat resistance in the case of a lining material using the curable resin composition.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2007-77218
Disclosure of Invention
Problems to be solved by the invention
The present invention aims to provide a resin composition for a photocurable backing material, which exhibits suitable thickening behavior and excellent curability, and which can give a cured backing material excellent in flexural strength, tensile elongation and heat resistance.
Means for solving the problems
The present inventors have found that a resin composition for a photocurable backing material containing a specific resin component, a thickener and a photopolymerization initiator can solve the above problems, and have completed the present invention.
Specifically, the present invention relates to a resin composition for a photocurable backing material, which comprises: a resin component (A) containing an epoxy (meth) acrylate (a 1) having a carboxyl group and an unsaturated monomer (a 2) as essential components, a thickener (B) and a photopolymerization initiator (C).
Effects of the invention
The photocurable backing material obtained from the resin composition for a photocurable backing material of the present invention is excellent in curability, and a cured backing material excellent in bending strength, tensile elongation and heat resistance can be obtained, so that it can be suitably used for pipe repair of sewer pipes and the like. Further, the prepreg can be used for repairing infrastructure such as gas pipes and electric power pipes, and repairing waterproof floors in bathrooms.
Detailed Description
The resin composition for a photocurable backing material of the present invention comprises: a resin component (A) containing an epoxy (meth) acrylate (a 1) having a carboxyl group and an unsaturated monomer (a 2) as essential components, a thickener (B) and a photopolymerization initiator (C).
In the present invention, "(meth) acrylate" means one or both of acrylate and methacrylate, and "(meth) acrylic acid" means one or both of acrylic acid and methacrylic acid.
The epoxy (meth) acrylate (a 1) having a carboxyl group is obtained, for example, by reacting an epoxy (meth) acrylate with an ester of a dibasic acid, and the dibasic acid is preferably an unsaturated dibasic acid, and more preferably maleic anhydride, from the viewpoint of further improving curability.
Examples of the dibasic acid include unsaturated dibasic acids such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, and itaconic anhydride; saturated dibasic acids such as phthalic acid, phthalic anhydride, halogenated phthalic anhydride, isophthalic acid, terephthalic acid, hexahydrophthalic anhydride, hexahydroterephthalic acid, hexahydroisophthalic acid, succinic anhydride, malonic acid, glutaric acid, adipic acid, sebacic acid, 1, 12-dodecanedioic acid, 2, 6-naphthalenedicarboxylic acid, 2, 7-naphthalenedicarboxylic acid, 2, 3-naphthalenedicarboxylic anhydride, 4' -biphthalic acid, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, nadic anhydride, methylnadic anhydride, and the like.
The epoxy (meth) acrylate is obtained, for example, by reacting an epoxy resin with (meth) acrylic acid.
Examples of the epoxy resin include bisphenol a type epoxy resins, bisphenol F type epoxy resins, bisphenol fluorene type epoxy resins, bisphenol type epoxy resins such as bisphenol fluorene type epoxy resins, phenol type epoxy resins such as phenol novolac type epoxy resins and cresol novolac type epoxy resins, oxazolidone modified epoxy resins, glycidyl ethers of phenols such as brominated epoxy resins of these resins, diglycidyl ether of dipropylene glycol, trimethylolpropane triglycidyl ether, diglycidyl ether of alkylene oxide adducts of bisphenol a, glycidyl ethers of polyhydric alcohols such as hydrogenated bisphenol a, alicyclic epoxy resins such as 3, 4-epoxy-6-methylcyclohexylmethyl-3, 4-epoxy-6-methylcyclohexane carboxylic acid esters, 1-epoxyethyl-3, 4-epoxycyclohexane, glycidyl esters such as phthalic acid diglycidyl ester, diglycidyl-p-hydroxybenzoic acid and dimer acid glycidyl esters, tetraglycidyl diaminodiphenylmethane, tetraglycidyl-m-xylylenediamine, triglycidyl-p-phenylene diamine, triglycidyl-N-aminophenol, glycidyl 3, 5-diglycidyl-d-m-glycidyl-3, 5-glycidyl, and the like, and the epoxy resin is more preferably a glycidyl resin having a better refractive index of 3, 3-glycidyl-p-glycidyl, 5-glycidyl-5-glycidyl, and the like, and a better curable epoxy resin from the aspect of the above. These epoxy resins may be used alone or in combination of 2 or more.
The reaction of the epoxy resin with (meth) acrylic acid is preferably carried out at 60 to 140℃using an esterification catalyst. In addition, a polymerization inhibitor or the like may be used.
The molar ratio (OH/COOH) of hydroxyl groups to carboxyl groups in the above-mentioned epoxy (meth) acrylate (a 1) having carboxyl groups is preferably 95/5 to 50/50, more preferably 90/10 to 60/40, from the viewpoint of exhibiting more suitable thickening behavior.
The acid value of the epoxy (meth) acrylate (a 1) having a carboxyl group is preferably 10 to 50, more preferably 15 to 40, from the viewpoint of obtaining a more suitable thickening behavior.
Examples of the unsaturated monomer (a 2) include monofunctional (meth) acrylate compounds such as benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, polyethylene glycol (meth) acrylate alkyl ether, polypropylene glycol (meth) acrylate alkyl ether, 2-ethylhexyl methacrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isotridecyl (meth) acrylate, n-stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentyl (meth) acrylate, and methyl methacrylate; di (meth) acrylate compounds such as ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, bisphenol di (meth) acrylate, and 1, 4-cyclohexanedimethanol di (meth) acrylate; among these, a polyfunctional (meth) acrylate compound such as trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate and the like tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate and the like, styrene, α -methylstyrene, vinyltoluene, diallyl phthalate, divinylbenzene and the like, and among these, a polyfunctional (meth) acrylate compound is preferably contained in view of excellent copolymerizability with the resin component (a) and further improvement in curability, flexural strength, tensile elongation and heat resistance. These unsaturated monomers may be used alone or in combination of 2 or more.
The mass ratio (a 1/a 2) of the radical curable resin (a 1) to the unsaturated monomer (a 2) is preferably in the range of 25/75 to 75/25, more preferably in the range of 30/70 to 70/30, from the viewpoint of further improving the balance between the resin impregnation property into the fiber and the curability.
The refractive index of the resin component (a) is preferably in the range of 1.530 to 1.550 from the viewpoint of further improvement in curability.
The resin component (a) contains the epoxy (meth) acrylate (a 1) and the unsaturated monomer (a 2) as essential components, but may contain other resin components.
Examples of the thickener (B) include metal oxides such as magnesium oxide, magnesium hydroxide, calcium oxide, and calcium hydroxide, metal hydroxides, isocyanate compounds, thermoplastic powder resins, and the like, and magnesium oxide is preferable from the viewpoint of obtaining more appropriate viscosity behavior. These thickeners may be used singly or in combination of 2 or more. In addition, in order to improve thickening behavior, a thickening aid such as a quaternary ammonium salt may be used in combination in addition to magnesium oxide as a thickener.
The amount of the thickener (B) to be used is preferably in the range of 0.1 to 15 parts by mass, more preferably in the range of 0.5 to 10 parts by mass, based on 100 parts by mass of the resin component (a), from the viewpoint of obtaining a more appropriate viscosity behavior.
Examples of the photopolymerization initiator (C) include acetophenone compounds such as 4-phenoxydichloroacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 2-methyl- [4- (methylthio) phenyl ] -2-morpholino-1-propanone, and 2, 2-dimethoxy-2-phenylacetophenone; benzoin compounds such as benzoin, benzoin methyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, 4-benzoyl-4 '-methyldiphenyl sulfide, and 3,3' -dimethyl-4-methoxybenzophenone; thioxanthone compounds such as thioxanthone, 2-chlorothioxanthone, 2, 4-dichlorothioxanthone, 2-methylthioxanthone, 2, 4-dimethylthioxanthone, 2, 4-diethylthioxanthone, isopropylthioxanthone and 2, 4-diisopropylthioxanthone; anthraquinone compounds such as 4,4 '-dimethylaminothioxanthone (alias=milbetone), 4' -diethylaminobenzophenone, α -acyloxime ester, benzil, methylbenzoyl formate ("Vicure 55"), 2-ethylanthraquinone; acyl phosphine oxide compounds such as 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide and bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide; 3,3', 4' -tetra (t-butylperoxycarbonyl) benzophenone, acrylated benzophenones, and the like. These photopolymerization initiators (C) may be used alone or in combination of 2 or more.
The amount of the photopolymerization initiator (C) used is preferably in the range of 0.1 to 3 parts by mass, more preferably in the range of 0.1 to 2 parts by mass, based on 100 parts by mass of the resin component (a), from the viewpoint of excellent curability.
The resin composition for a photocurable backing material of the present invention contains a resin component (a), a thickener (B) and a photopolymerization initiator (C), and may contain other additives as required.
Examples of the other additives include polymerization inhibitors, antioxidants, light stabilizers, solvents, antifoaming agents, thixotropic agents, leveling agents, tackifiers, antistatic agents, flame retardants, curing accelerators, pigments, fillers, reinforcing materials, and aggregates.
The photocurable backing material of the present invention comprises the above-mentioned resin composition for a photocurable backing material and a glass fiber reinforcement.
Examples of the form of the glass fiber reinforced material include a woven fabric in which a roving is woven in a plain weave, a chopped strand mat in which chopped strands cut into 2 inches are randomly oriented and bonded with an adhesive to form a nonwoven fabric, a unidirectional sheet in which the roving is aligned in the same direction and bonded with an auxiliary weft and an adhesive, a multiaxial sewn substrate in which the sheets aligned in one direction are laminated in a plurality of directions and bonded with a stitch, and a sewn mat in which the sheet aligned in one direction and the chopped strands oriented randomly are bonded with a stitch. These glass fiber reinforcements may be used alone or in combination of 2 or more.
As the glass fiber, for example, glass fibers obtained from alkali-containing glass (C glass), low alkali glass, alkali-free glass (E glass) or the like as a raw material can be used, but it is preferable to use acid-resistant glass (ECR glass) excellent in mechanical properties and corrosion resistance in infrastructure repair applications.
The content of the glass fiber reinforcement in the photocurable backing material of the present invention is preferably in the range of 30 to 60 mass% from the viewpoint of further improvement of mechanical properties.
As a method for constructing and applying the lining material of the present invention, there is a method of forming a lining material layer by directly laminating and impregnating the photocurable lining resin composition of the present invention and a glass fiber reinforcement on a repair surface of concrete or the like; a method in which the photocurable backing resin composition of the present invention and a glass fiber reinforcement are laminated and impregnated in advance in a factory or the like to prepare a prepreg covered with a film on both surfaces, the film on the surface to be bonded is peeled off as needed at a repair site, and then the prepreg is pressed and bonded with a roll or the like according to the shape of the repair site, and cured by irradiation with light.
Examples of the method for curing the photocurable backing material of the present invention include a method of irradiating ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays, and specific examples of the energy source or curing device include a germicidal lamp, a fluorescent lamp for ultraviolet rays, a carbon arc, a xenon lamp, a high-pressure mercury lamp for copying, a medium-pressure or high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, an electrodeless lamp, a metal halide lamp, a fluorescent chemical lamp, an LED lamp, ultraviolet rays using natural light as a light source, and an electron beam using a scanning type or curtain type electron beam accelerator.
The photocurable lining material of the present invention is excellent in rapid curability and thick film curability, and therefore can be suitably used for pipe repair of sewer pipes and the like. Further, the prepreg can be used for repairing infrastructure such as gas pipes and electric power pipes, and repairing waterproof floors in bathrooms.
Examples
Hereinafter, the present invention will be described in more detail with reference to specific examples. The refractive index of the resin component was measured using a general Abbe refractometer (ERMA, co., ltd. "ER-7 MW"), the acid value was measured in accordance with JIS-K-6901, and the epoxy equivalent was measured in accordance with JIS-K-7236.
( Synthesis example 1: synthesis of epoxy (meth) acrylate (a 1-1) having carboxyl group )
In a 2L flask equipped with a thermometer, nitrogen inlet tube, and stirrer, 488.8 parts by mass of bisphenol a type epoxy resin (epicolin 850, epoxy equivalent 188, manufactured by DIC corporation), 215.7 parts by mass of methacrylic acid, and 0.25 parts by mass of tertiary butylhydroquinone were charged under a gas flow atmosphere in which nitrogen and air were mixed in a ratio of 1 to 1, and after the temperature was raised to 90 ℃ for 1 hour, 0.7 part by mass of 2-methylimidazole was added, and the reaction temperature was raised to 110 ℃ for 2 hours. Then, 0.7 part by mass of 2-methylimidazole was further added thereto, and the acid value and the epoxy equivalent were measured. After confirming that the acid value was 7.0 or less and the epoxy equivalent was 5000 or more, the reaction was terminated. After cooling to around 40 ℃, 0.05 parts by mass of t-butylhydroquinone and 300 parts by mass of phenoxyethyl methacrylate were added and dissolved. After stirring for 10 minutes, 75.4 parts by mass of maleic anhydride was added thereto, and the mixture was heated to 90℃to react for 5 hours. Then, it was confirmed that the acid value was 50 or less, and the reaction was terminated. After cooling to around 50 ℃, the mixture was taken out of the reaction vessel and used as a maleic acid-modified epoxy (meth) acrylate to obtain a carboxyl group-containing epoxy (meth) acrylate (a 1-1) having a molar ratio of hydroxyl groups to carboxyl groups (OH/COOH) of 70/30. The acid value was 50.0.
( Synthesis example 2: synthesis of epoxy (meth) acrylate (a 1-2) )
368.3 parts by mass of bisphenol A epoxy resin (EPICLON 850, epoxy equivalent 188, manufactured by DIC Co., ltd.) was charged into a 2L flask equipped with a thermometer, a nitrogen inlet tube, and a stirrer under nitrogen flow, heated to 60℃and then 83.4 parts by mass of bisphenol A was added thereto, and the temperature was raised to 110 ℃. Then, 0.55 parts by mass of 2-methylimidazole was added to confirm that the epoxy equivalent was within a range of 375.+ -. 10, and the mixture was cooled to 100 ℃. After nitrogen removal using a vacuum pump, air displacement was performed. Then, 102.2 parts by mass of methacrylic acid and 0.20 parts by mass of t-butylhydroquinone were charged at 100℃under a gas flow atmosphere in which nitrogen and air were mixed in a 1-to-1 ratio, reacted for 2 hours, then 0.277 parts by mass of 2-methylimidazole was added, the acid value and the epoxy equivalent were measured, the acid value was found to be 7.0 or less and the epoxy equivalent was found to be 5000 or more, and then 0.05 parts by mass of t-butylhydroquinone and 277 parts by mass of phenoxyethyl methacrylate were added and dissolved. After stirring for 10 minutes, 39.6 parts by mass of maleic anhydride was added thereto, and the temperature was raised to 90℃to react for 5 hours. After confirming that the acid value was 30 or less, the reaction was terminated. After cooling to around 50 ℃, the mixture was taken out of the reaction vessel and used as a maleic acid-modified epoxy (meth) acrylate to obtain a carboxyl group-containing epoxy (meth) acrylate (a 1-2) having a hydroxyl group to carboxyl group molar ratio (OH/COOH) of 80/20. The acid value was 27.0.
Synthesis example 3 Synthesis of unsaturated polyester resin (1)
To a 2L flask equipped with a thermometer, a nitrogen inlet tube and a stirrer were added 416 parts by mass of neopentyl glycol, 76 parts by mass of propylene glycol, 332 parts by mass of isophthalic acid and 294 parts by mass of maleic anhydride, and the mixture was fed in portions by a two-stage reaction according to a conventional method, and the temperature was raised to 200 ℃. It was confirmed that the acid value was 25 or less, and the reaction was terminated. After cooling the obtained unsaturated polyester to 130 ℃, 0.015 parts by mass of hydroquinone was added to 100 parts by mass of the obtained unsaturated polyester, and after further cooling to 60 ℃, the unsaturated polyester resin (1) was obtained by taking out from the reaction vessel. The acid value was 24.0.
( Synthesis example 4: synthesis of epoxy (meth) acrylate (Ra 1-1) )
In a 2L flask equipped with a thermometer, nitrogen inlet tube, and stirrer, 488.8 parts by mass of bisphenol a type epoxy resin (epicolin 850, epoxy equivalent 188, manufactured by DIC corporation), 215.7 parts by mass of methacrylic acid, and 0.25 parts by mass of tertiary butylhydroquinone were charged under a gas flow atmosphere in which nitrogen and air were mixed in a ratio of 1 to 1, and after the temperature was raised to 90 ℃ for 1 hour, 0.7 part by mass of 2-methylimidazole was added, and the reaction temperature was raised to 110 ℃ for 2 hours. Then, 0.7 part by mass of 2-methylimidazole was further added thereto, and the acid value and the epoxy equivalent were measured. After confirming that the acid value was 7.0 or less and the epoxy equivalent was 5000 or more, the reaction was terminated. After cooling to around 50 ℃, 0.05 parts by mass of t-butylhydroquinone was added thereto, and the mixture was taken out of the reaction vessel to obtain epoxy (meth) acrylate (Ra 1-1). The acid value was 3.0.
( Example 1: production of resin composition (1) for photocurable backing Material )
The resin composition (1) for a photocurable backing material was obtained by mixing 60 parts by mass of the epoxy (meth) acrylate (a 1-1) having a carboxyl group obtained in synthesis example 1, 25 parts by mass of phenoxyethyl methacrylate, 15 parts by mass of diethylene glycol dimethacrylate, 1.5 parts by mass of bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide (hereinafter abbreviated as "photopolymerization initiator (C-1)") and 3.0 parts by mass of a thickener (magmicro (japanese: man-made, registered trademark) MD504-2", hereinafter abbreviated as" thickener (B-1) ") manufactured by imperial pigment co.
The refractive index of the resin component (A-1) containing the epoxy (meth) acrylate (a 1-1), phenoxyethyl methacrylate, and diethylene glycol dimethacrylate was 1.530.
( Example 2: production and evaluation of resin composition (2) for photocurable backing Material )
40 parts by mass of the epoxy (meth) acrylate (a 1-2) having a carboxyl group obtained in Synthesis example 2, 40 parts by mass of phenoxyethyl methacrylate, 20 parts by mass of trimethylolpropane trimethacrylate, 1.5 parts by mass of a photopolymerization initiator (C-1), and 2.0 parts by mass of a thickener (B-1) were mixed to obtain a resin composition (2) for a photocurable backing material.
The refractive index of the resin component (A-2) containing the epoxy (meth) acrylate (a 1-1), phenoxyethyl methacrylate, and trimethylolpropane trimethacrylate was 1.530.
( Comparative example 1: preparation and evaluation of resin composition (R1) for photocurable backing Material )
The unsaturated polyester resin (1) obtained in Synthesis example 3 was mixed with 40 parts by mass, phenoxyethyl methacrylate 40 parts by mass, trimethylolpropane trimethacrylate 20 parts by mass, photopolymerization initiator (C-1) 1.5 parts by mass, and thickener (B-1) 2.0 parts by mass to obtain a resin composition (R1) for a photocurable backing material.
The refractive index of the resin component (RA-1) comprising the unsaturated polyester resin (1), phenoxyethyl methacrylate and trimethylolpropane trimethacrylate was 1.510.
( Comparative example 2: preparation and evaluation of resin composition (R2) for photocurable backing Material )
60 parts by mass of the epoxy (meth) acrylate (Ra 1-1), 25 parts by mass of phenoxyethyl methacrylate, 15 parts by mass of diethylene glycol dimethacrylate, 1.5 parts by mass of the photopolymerization initiator (C-1), and 3.0 parts by mass of the thickener (B-1) obtained in Synthesis example 4 were mixed to obtain a resin composition (R2) for a photocurable backing material.
The refractive index of the resin component (RA-2) containing epoxy (meth) acrylate (Ra 1-1), phenoxyethyl methacrylate, and diethylene glycol dimethacrylate was 1.530.
[ thickening behavior ]
The resin composition for a photocurable backing material obtained as described above was measured for viscosity at a liquid temperature of 25℃using a Brookfield viscometer (BF rotary viscometer, manufactured by DONGMENTO INDUSTRIAL Co., ltd.). Further, the viscosity after standing at 25℃for 24 hours was measured, and the thickening behavior was evaluated according to the following criteria.
And (2) the following steps: the viscosity after 24 hours is 1000 dPa.s or more and less than 20000 dPa.s
X: viscosity after 24 hours is less than 1000 dPa.s or 20000 dPa.s
[ evaluation of physical Properties of cured product ]
The surface of the resin composition for a photocurable backing material obtained as described above was irradiated with a metal halide lamp M045-31L (emission length: 375mm,4.5 kW) manufactured by EYE GRAPHICS Co., ltd.) having a cold mirror at a height of 20cm for 300 seconds to obtain a cured product, and various physical properties were evaluated.
[ bending Strength ]
The cured product obtained above was measured for flexural strength according to JIS K7171-1, and evaluated according to the following criteria.
O: 100MPa or more
X: less than 100MPa
[ tensile elongation ]
The cured product obtained above was subjected to a tensile test of 1B test pieces according to JIS K7161-1 and 2, and the tensile elongation was measured and evaluated according to the following criteria.
O: more than 2 percent
X: less than 2%
[ Heat resistance ]
The heat resistance of the cured product obtained above was evaluated based on the following criteria by measuring the load deflection temperature according to JIS K7191-1.
O: above 85 DEG C
O: less than 85 DEG C
The evaluation results of the resin compositions (1) to (2) and (R1) to (R2) for the photocurable backing material obtained in the above are shown in table 1.
TABLE 1
It was confirmed that the photocurable backing material obtained from the resin composition for a photocurable backing material of the present invention of examples 1 to 2 was excellent in thickening behavior and the cured product thereof was excellent in flexural strength, tensile elongation and heat resistance.
On the other hand, comparative example 1 was an example in which an unsaturated polyester resin was used instead of the epoxy (meth) acrylate (a 1) having a carboxyl group, and it was confirmed that the bending strength and heat resistance were insufficient.
Comparative example 2 was an example in which epoxy (meth) acrylate (a 1) having no carboxyl group was used instead of epoxy (meth) acrylate (a 1) having a carboxyl group, and it was confirmed that the thickening property was insufficient.
Claims (7)
1. A resin composition for a photocurable backing material, characterized by comprising: a resin component (A) containing an epoxy (meth) acrylate (a 1) having a carboxyl group and an unsaturated monomer (a 2) as essential components, a thickener (B) and a photopolymerization initiator (C).
2. The resin composition for a photocurable backing material according to claim 1, wherein a mass ratio of the epoxy (meth) acrylate (a 1) having a carboxyl group to the unsaturated monomer (a 2), i.e., a1/a2, is in a range of 25/75 to 75/25.
3. The resin composition for a photocurable backing material according to claim 1 or 2, wherein the epoxy (meth) acrylate (a 1) having a carboxyl group is a reaction product of an epoxy (meth) acrylate and a dibasic acid.
4. The resin composition for a photocurable backing material according to any one of claims 1 to 3, wherein the unsaturated monomer (a 2) comprises a polyfunctional (meth) acrylate.
5. The resin composition for a photocurable backing material according to any one of claims 1 to 4, wherein the thickener (B) is magnesium oxide.
6. A photocurable backing material comprising: the resin composition for a photocurable backing material as recited in any one of claims 1-5, and a glass fiber reinforcement.
7. The cured product of the photocurable backing material as recited in claim 6.
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| JP2020-163205 | 2020-09-29 | ||
| JP2020163205 | 2020-09-29 | ||
| PCT/JP2021/033080 WO2022070816A1 (en) | 2020-09-29 | 2021-09-09 | Photocurable resin composition for lining material, photocurable lining material and cured product thereof |
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- 2021-09-09 WO PCT/JP2021/033080 patent/WO2022070816A1/en active Application Filing
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