JP2016204431A - 嫌気硬化性組成物 - Google Patents
嫌気硬化性組成物 Download PDFInfo
- Publication number
- JP2016204431A JP2016204431A JP2015084435A JP2015084435A JP2016204431A JP 2016204431 A JP2016204431 A JP 2016204431A JP 2015084435 A JP2015084435 A JP 2015084435A JP 2015084435 A JP2015084435 A JP 2015084435A JP 2016204431 A JP2016204431 A JP 2016204431A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- component
- curable composition
- chelating agent
- anaerobic
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000000178 monomer Substances 0.000 claims abstract description 63
- 239000002738 chelating agent Substances 0.000 claims abstract description 48
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 10
- -1 acryl Chemical group 0.000 claims description 59
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 50
- 239000007788 liquid Substances 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 4
- 229940081974 saccharin Drugs 0.000 claims description 4
- 235000019204 saccharin Nutrition 0.000 claims description 4
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 8
- 238000012790 confirmation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 229910002012 Aerosil® Inorganic materials 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 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 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 2
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SZHQPBJEOCHCKM-UHFFFAOYSA-N 2-phosphonobutane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CCC(P(O)(O)=O)(C(O)=O)CC(O)=O SZHQPBJEOCHCKM-UHFFFAOYSA-N 0.000 description 2
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- IAXXETNIOYFMLW-GYSYKLTISA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C(=C)C)C[C@@H]1C2(C)C IAXXETNIOYFMLW-GYSYKLTISA-N 0.000 description 2
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 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 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
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
- 230000006355 external stress Effects 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 1
- VMFJVWPCRCAWBS-UHFFFAOYSA-N (3-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 VMFJVWPCRCAWBS-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- HDMHXSCNTJQYOS-UHFFFAOYSA-N 1-(4-prop-2-enylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(CC=C)C=C1 HDMHXSCNTJQYOS-UHFFFAOYSA-N 0.000 description 1
- JFZVSHAMRZPOPA-UHFFFAOYSA-N 1-[n-(2-hydroxypropyl)-4-methylanilino]propan-2-ol Chemical compound CC(O)CN(CC(C)O)C1=CC=C(C)C=C1 JFZVSHAMRZPOPA-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical group CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- LBNDGEZENJUBCO-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethyl]butanedioic acid Chemical compound CC(=C)C(=O)OCCC(C(O)=O)CC(O)=O LBNDGEZENJUBCO-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- RAEOEMDZDMCHJA-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O RAEOEMDZDMCHJA-UHFFFAOYSA-N 0.000 description 1
- XNCSCQSQSGDGES-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]propyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C(C)CN(CC(O)=O)CC(O)=O XNCSCQSQSGDGES-UHFFFAOYSA-N 0.000 description 1
- DMQQXDPCRUGSQB-UHFFFAOYSA-N 2-[3-[bis(carboxymethyl)amino]propyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCCN(CC(O)=O)CC(O)=O DMQQXDPCRUGSQB-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-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
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-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
- WNXTZVMMNCCZTP-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate 5-hydroxy-2-methylpent-2-enoic acid Chemical compound OCCC=C(C(=O)O)C.C(C(=C)C)(=O)OCCO WNXTZVMMNCCZTP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- ZPQAUEDTKNBRNG-UHFFFAOYSA-N 2-methylprop-2-enoylsilicon Chemical compound CC(=C)C([Si])=O ZPQAUEDTKNBRNG-UHFFFAOYSA-N 0.000 description 1
- LEUJIOLEGDAICX-UHFFFAOYSA-N 3-chloroxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(Cl)C=C3OC2=C1 LEUJIOLEGDAICX-UHFFFAOYSA-N 0.000 description 1
- KMSYDDGPKBBSNA-UHFFFAOYSA-N 3-ethyl-1-phenylpentan-1-one Chemical compound CCC(CC)CC(=O)C1=CC=CC=C1 KMSYDDGPKBBSNA-UHFFFAOYSA-N 0.000 description 1
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- DLGLWFGFEQRRCP-UHFFFAOYSA-N 6-chloro-1-nonylxanthen-9-one Chemical compound O1C2=CC(Cl)=CC=C2C(=O)C2=C1C=CC=C2CCCCCCCCC DLGLWFGFEQRRCP-UHFFFAOYSA-N 0.000 description 1
- 229910002014 Aerosil® 130 Inorganic materials 0.000 description 1
- 229910002015 Aerosil® 150 Inorganic materials 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 229910002017 Aerosil® 255 Inorganic materials 0.000 description 1
- 229910002018 Aerosil® 300 Inorganic materials 0.000 description 1
- 229910002019 Aerosil® 380 Inorganic materials 0.000 description 1
- 229910002013 Aerosil® 90 Inorganic materials 0.000 description 1
- WMONOXOCMIPNNU-UHFFFAOYSA-N C=CC(=O)OCCCC(O)COC(=O)C1=CC=CC=C1C(O)=O Chemical compound C=CC(=O)OCCCC(O)COC(=O)C1=CC=CC=C1C(O)=O WMONOXOCMIPNNU-UHFFFAOYSA-N 0.000 description 1
- AFUWHLXUBJOPNO-UHFFFAOYSA-N CCCCCCCCCCCCCCCC[SiH3] Chemical compound CCCCCCCCCCCCCCCC[SiH3] AFUWHLXUBJOPNO-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229940120146 EDTMP Drugs 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical compound OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 1
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 description 1
- SZEXXTYGQYKIHJ-UHFFFAOYSA-N O.O.O.O.[Na].[Na].[Na].[Na] Chemical compound O.O.O.O.[Na].[Na].[Na].[Na] SZEXXTYGQYKIHJ-UHFFFAOYSA-N 0.000 description 1
- XMEKHKCRNHDFOW-UHFFFAOYSA-N O.O.[Na].[Na] Chemical compound O.O.[Na].[Na] XMEKHKCRNHDFOW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 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
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000004205 dimethyl polysiloxane 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
- 238000004090 dissolution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- DJQJFMSHHYAZJD-UHFFFAOYSA-N lidofenin Chemical compound CC1=CC=CC(C)=C1NC(=O)CN(CC(O)=O)CC(O)=O DJQJFMSHHYAZJD-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical compound CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 230000000576 supplementary effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:キレート剤および(メタ)アクリルモノマー
(C)成分:嫌気硬化触媒
(D)成分:有機過酸化物
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:(B−1)成分として、25℃で固形のキレート剤を溶解させる(メタ)アクリルモノマーにより25℃で固形のキレート剤を溶解させた組成物
(C)成分:嫌気硬化触媒
(D)成分:有機過酸化物
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:(B−2)成分として、25℃で液状のキレート剤と相溶する(メタ)アクリルモノマーにより25℃で液状のキレート剤を相溶させた組成物
(C)成分:嫌気硬化触媒
(D)成分:有機過酸化物
組成物を調製するために下記成分を準備した。
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
・両末端に(メタ)アクリル基を有するオリゴマー(粘度:470Pa・s)(RC−200C 株式会社カネカ製)
・両末端に(メタ)アクリル基を有するオリゴマー(粘度:230Pa・s)(RC−100C 株式会社カネカ製)
(メタ)アクリルモノマー
・イソボルニルメタクリレート(ライトエステルIB−X 共栄社化学株式会社製)
・メタクリル酸2−ヒドロキシエチル(2−ヒドロキシエチルメタクリレート)(HEMA 株式会社日本触媒製)
・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製)
・トリエチレングリコールジメタクリレート(3G 新中村化学工業株式会社製)
・2−メタクリロイロキシエチルコハク酸(ライトエステルHO−MS 共栄社化学株式会社)
・2−ヒドロキシエチルメタクリレートアシッドホスフェート(JPA−514 城北化学工業株式会社製)
・2−メタクロイロキシエチルアシッドホスフェート(ライトエステルP−1M 共栄社化学株式会社製)
・2−メタクロイロキシエチルアシッドホスフェート(MR−200 大八化学工業株式会社製)
キレート剤
・エチレンジアミン−N,N,N’,N’−四酢酸二ナトリウム塩二水和物(25℃で固体)(2NA(EDTA・2Na) 株式会社同人化学研究所製)
・エチレンジアミン−N,N,N’,N’−四酢酸四ナトリウム塩四水和物(25℃で固体)(4NA(EDTA・4Na) 株式会社同人化学研究所製)
・アミノカルボン酸塩(25℃で液体)(MZ−8 キレスト株式会社製)
(B−1)成分:25℃で固形のキレート剤を溶解させる(メタ)アクリルモノマーにより25℃で固形のキレート剤を溶解させた組成物
[マスター1]
・90質量部のJPA−514に対して、EDTA2Naを10質量部添加して50℃雰囲気下で2時間攪拌する。EDTA2NaのJPA−514溶液をマスター1と呼ぶ。
[マスター2]
・90質量部のP−1Mに対して、EDTA2Naを10質量部添加して50℃雰囲気下で2時間攪拌する。EDTA2NaのP−1M溶液をマスター2と呼ぶ。
[マスター3]
・90質量部のMR−200に対して、1EDTA2Naを10質量部添加して50℃雰囲気下で2時間攪拌する。EDTA2NaのMR−200溶液をマスター3と呼ぶ。
(B−2)成分:25℃で液状のキレート剤と相溶する(メタ)アクリルモノマーにより25℃で液状のキレート剤を相溶させた組成物
[マスター4]
・99質量部のHEMAに対して、MZ−8を1質量部添加して1時間攪拌する。MZ−8のHEMA溶液をマスター4と呼ぶ。
(C)成分:嫌気硬化触媒
・サッカリン(試薬)
(D)成分:有機過酸化物
・クメンハイドロパーオキサイド(パークミルH−80 日本油脂株式会社製)
硬化促進剤
・ベンゾチアゾール(試薬)
・p−メトキシフェノール(試薬)
・ドデカンチオール(試薬)
重合禁止剤
・2,6−ジ−t−ブチル−4−メチルフェノール(BHT)(試薬)
・ヒドロキノン(HQ)(試薬)
その他
・1−ベンジル−2−メチルイミダゾール(キュアゾール1B2MZ 四国化成工業株式会社製)
・2−エチル−4−メチルイミダゾール(キュアゾール2E4MZ 四国化成工業株式会社製)
前記(メタ)アクリルモノマーを攪拌容器に秤量した後、前記キレート剤を秤量して攪拌容器に添加する。参考1〜16は50℃雰囲気下で2時間攪拌し、参考17〜21は25℃雰囲気かで2時間攪拌する。詳細な調製量は表1と表2に従い、数値は全て質量部で表記する。
参考例1〜16については25℃まで冷ませる。参考1〜21に対して目視で、下記の評価基準に従い、溶解性または相溶性の確認を行う。(A)成分との相溶を考慮すると、「○」であることが好ましい。
評価基準
○:透明
△:白濁
×:不溶
(A)成分、(メタ)アクリルモノマー、(B)成分(またはキレート剤)(C)成分、および重合禁止剤を攪拌釜に秤量し、50℃に加熱し8時間程度攪拌する。その後、室温に戻し(D)成分および硬化促進剤を秤量して攪拌釜に投入して、1時間攪拌した。詳細な調製量は表3に従い、数値は全て質量部で表記する。
製造直後の状態を目視にて確認し、下記の評価基準により判断した。透明であることで各成分が完全に混ざっていると判断できるため、「○」であることが好ましい。ここで、ゲル化とは反応させていないにもかかわらず、粘度が高くなった状態を言う。
評価基準
○:透明で分離・ゲル化が無い
×:ゲル化が有る
××:分離が有る
製造直後の各組成物を80℃×30分に放置して、性状を目視で確認する。性状確認で性状が「×」の場合は、確認が出来ないため「未測定」と表記する。当該保存安定性確認は、25℃雰囲気下の保存安定性と相関があり、「○」であることが好ましい。
評価基準
○:ゲル化しない
×:ゲル化した
M10、P1.5×20mmの金剛鋲螺製の六角ボルト(JIS B1180)、M10、P=1.5の紀州ファスナー製の六角ナットを使用した。ボルトの雄ねじ部分先端約10mmに組成物を6点塗布し、ナットに挿入して、ボルトは最後まで締め込まなかった。そのままの状態で25℃で24時間放置し、組成物を硬化させた。ナットを接着したボルトは、ボルトの頭を万力で固定し、トルクレンチによりナットを回転させ、ナットが初めて動き出す時の強度を「トルク(N・m)」として測定する。硬化が完了している目安としては、5MPa以上であれば良い。また、性状確認で性状が「×」または「××」の場合は組成物そのものが調製できず、トルク測定が出来ないため「未測定」と表記する。
Claims (10)
- (A)〜(D)成分を含む嫌気硬化性組成物。
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:キレート剤および(メタ)アクリルモノマー
(C)成分:嫌気硬化触媒
(D)成分:有機過酸化物 - (A)〜(D)成分を含む嫌気硬化性組成物。
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:(B−1)成分として、25℃で固形のキレート剤を溶解させる(メタ)アクリルモノマーにより25℃で固形のキレート剤を溶解させた組成物
(C)成分:嫌気硬化触媒
(D)成分:有機過酸化物 - 請求項2の(B)成分に記載されるキレート剤を溶解させる(メタ)アクリルモノマーが、リン酸エステルを骨格に有する(メタ)アクリルモノマーである請求項2に記載の嫌気硬化性組成物。
- 請求項2または3のいずれかの(B)成分に記載されているキレート剤を溶解させる(メタ)アクリルモノマーが、以下の構造である請求項2または3のいずれかに記載の嫌気硬化性組成物。
(ここで、nは1または2であり、R1は水素またはメチル基を、R2は炭素数が1〜5の炭化水素基を示す。) - (A)〜(D)成分を含む嫌気硬化性組成物。
(A)成分:(メタ)アクリルモノマーを重合させた主骨格を有し、主骨格の末端に(メタ)アクリル基を有するオリゴマー
(B)成分:(B−2)成分として、25℃で液状のキレート剤と相溶する(メタ)アクリルモノマーにより25℃で液状のキレート剤を相溶させた組成物
(C)成分:嫌気硬化触媒
(D)成分:有機過酸化物 - 請求項5の(B)成分に記載されるキレート剤と相溶する(メタ)アクリルモノマーが、分子中に水酸基および/またはカルボキシル基を有する(メタ)アクリルモノマーである請求項5に記載の嫌気硬化性組成物。
- 請求項6の(B)成分に記載されるキレート剤と相溶する水酸基を有する(メタ)アクリルモノマーが、以下の構造である請求項6に記載の嫌気硬化性組成物。
(ここで、R1は水素またはメチル基を、R2は炭素数が1〜5の炭化水素基を示す。) - 前記(C)成分がサッカリンである請求項1〜7のいずれかに記載の嫌気硬化性組成物。
- さらに、硬化促進剤を含む請求項1〜8のいずれかに記載の嫌気硬化性組成物。
- さらに、重合禁止剤を含む請求項1〜9のいずれかに記載の嫌気硬化性組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015084435A JP6504351B2 (ja) | 2015-04-16 | 2015-04-16 | 嫌気硬化性組成物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015084435A JP6504351B2 (ja) | 2015-04-16 | 2015-04-16 | 嫌気硬化性組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016204431A true JP2016204431A (ja) | 2016-12-08 |
JP6504351B2 JP6504351B2 (ja) | 2019-04-24 |
Family
ID=57488941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015084435A Active JP6504351B2 (ja) | 2015-04-16 | 2015-04-16 | 嫌気硬化性組成物 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6504351B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108977087A (zh) * | 2018-06-22 | 2018-12-11 | 深圳市郎搏万先进材料有限公司 | 一种厌氧胶及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51132234A (en) * | 1975-04-21 | 1976-11-17 | Suriibondo:Kk | An anaerobic adhesive composition |
US7728092B1 (en) * | 2006-04-13 | 2010-06-01 | Henkel Corporation | Anaerobically curable compositions |
-
2015
- 2015-04-16 JP JP2015084435A patent/JP6504351B2/ja active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51132234A (en) * | 1975-04-21 | 1976-11-17 | Suriibondo:Kk | An anaerobic adhesive composition |
US7728092B1 (en) * | 2006-04-13 | 2010-06-01 | Henkel Corporation | Anaerobically curable compositions |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108977087A (zh) * | 2018-06-22 | 2018-12-11 | 深圳市郎搏万先进材料有限公司 | 一种厌氧胶及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP6504351B2 (ja) | 2019-04-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8273827B2 (en) | Adhesive composition and adhesion method | |
JP6374607B2 (ja) | ノボラック系ビニルエステルを有する嫌気硬化性組成物 | |
JP6503736B2 (ja) | 二液型硬化性樹脂組成物 | |
JP6015667B2 (ja) | 二液型硬化性樹脂組成物 | |
TW201809023A (zh) | 組成物 | |
TWI808784B (zh) | 樹脂組成物、接著劑、密封劑、壩劑(dam agent)及半導體裝置 | |
JP2017210573A (ja) | 組成物 | |
EP2449047B1 (en) | Ultrafast heat/room temperature adhesive composition for bonding applications | |
JP2019519635A (ja) | 反応性シルセスキオキサンを含む接着剤組成物 | |
JP2018172565A (ja) | アクリル系硬化性樹脂組成物 | |
JP6766315B2 (ja) | 嫌気硬化性組成物 | |
JP6504351B2 (ja) | 嫌気硬化性組成物 | |
JP6327518B2 (ja) | 光硬化性組成物 | |
JPS6316430B2 (ja) | ||
JP7196460B2 (ja) | 二剤型アクリル系接着剤組成物、それにより接合された接合体 | |
WO2005010056A1 (ja) | 嫌気硬化性組成物 | |
JP6902198B2 (ja) | 嫌気硬化性組成物 | |
US11505692B2 (en) | (Meth) acrylic resin composition and electroconductive adhesive using the same | |
JP2012219136A (ja) | アクリル樹脂系接着剤組成物 | |
JP2014088458A (ja) | アクリル系接着剤組成物 | |
CN117999299A (zh) | 组合物、接着剂及接合体 | |
WO2023074601A1 (ja) | 嫌気硬化性組成物 | |
WO2022249965A1 (ja) | 耐熱性アクリル系接着剤組成物 | |
JPH0460510B2 (ja) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180221 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20181219 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190116 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190214 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190227 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190312 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6504351 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |