WO2017154616A1 - Anaerobic curable resin composition and sealant for welch plug in which same is used - Google Patents
Anaerobic curable resin composition and sealant for welch plug in which same is used Download PDFInfo
- Publication number
- WO2017154616A1 WO2017154616A1 PCT/JP2017/007051 JP2017007051W WO2017154616A1 WO 2017154616 A1 WO2017154616 A1 WO 2017154616A1 JP 2017007051 W JP2017007051 W JP 2017007051W WO 2017154616 A1 WO2017154616 A1 WO 2017154616A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- component
- curable resin
- resin composition
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 35
- 239000000565 sealant Substances 0.000 title description 10
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 8
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 105
- -1 glycerin fatty acid ester Chemical class 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 235000011187 glycerol Nutrition 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 239000010419 fine particle Substances 0.000 abstract description 7
- 230000002528 anti-freeze Effects 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 150000005215 alkyl ethers Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 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
- 230000000052 comparative effect Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
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- 239000000853 adhesive Substances 0.000 description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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- 239000003093 cationic surfactant Substances 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
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- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- 229940081974 saccharin Drugs 0.000 description 4
- 235000019204 saccharin Nutrition 0.000 description 4
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 208000034189 Sclerosis Diseases 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000012790 confirmation Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 2
- BTUUFEOXIVJCMZ-UHFFFAOYSA-N 1-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-2-phenoxyundecan-2-ol Chemical compound OCCOCCOCCOCC(O)(CCCCCCCCC)OC1=CC=CC=C1 BTUUFEOXIVJCMZ-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 2
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 2
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- XXHDHAPOSIFMIG-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-phenoxyethanol Chemical compound OCCOCCOCCOCC(O)OC1=CC=CC=C1 XXHDHAPOSIFMIG-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-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
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 239000005062 Polybutadiene Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
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- 230000003078 antioxidant effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
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- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-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
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
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- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 1
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- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- OBNIRVVPHSLTEP-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(O)COCCO OBNIRVVPHSLTEP-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
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- 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
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- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- TVWGHFVGFWIHFN-UHFFFAOYSA-N 2-hexadecan-2-yl-4,6-dimethylphenol Chemical compound CCCCCCCCCCCCCCC(C)C1=CC(C)=CC(C)=C1O TVWGHFVGFWIHFN-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Definitions
- the present invention relates to an anaerobic curable resin composition having a characteristic that a cured product is brittle and is easily formed into fine particles. Furthermore, this invention relates to the sealing agent for welch plugs using the said anaerobic curable resin composition.
- the anaerobic curable resin composition is mainly composed of a compound having a radical polymerizable functional group such as (meth) acrylate, and is stable while being in contact with oxygen present in the air, gelled, etc.
- the liquid is kept in a liquid state for a long time without causing a radical polymerization reaction to proceed rapidly when oxygen is shut off.
- the anaerobic curable resin composition is used for bonding and fixing screws, bolts, etc., fixing of fitting parts, bonding, sealing, filling of burrows that can occur in cast parts, and the like. .
- anaerobic curable resin compositions are frequently used in automobile parts, such as an adhesive seal between engine flanges and a weld plug of an engine block.
- Patent Document 2 discloses a (meth) acrylic curable composition containing an anionic surfactant, and the curable composition is eluted in an antifreeze solution. Even with high curability.
- the present inventors have discovered that when the curable composition described in Patent Document 2 is used as an adhesive sealant for a Welch plug, the cured product stops the movement of valves and fans.
- the cause is that the cured product obtained by curing the curable composition of Patent Document 2 in the antifreeze liquid breaks when a load is applied, but the size of the grains is 1 mm or more. It may be possible to stop the movement.
- the present invention has been made in view of the above situation, and an object of the present invention is to provide an anaerobic curable resin composition having such characteristics that a cured product is brittle and is easily formed into fine particles.
- Another object of the present invention is to provide a sealing agent for a welch plug using the anaerobic curable resin composition.
- the present inventors have found an anaerobic curable resin composition and a technique relating to a seal material for a welch plug using the same, and have reached the present invention.
- the present invention is as follows.
- Anaerobic curable resin composition containing the following components (A) to (D): (A) component: a compound having a radical polymerizable functional group, (B) component: radical polymerization initiator, (C) component: anaerobic polymerization accelerator, (D) Component: Nonionic surfactant.
- the compound having a radically polymerizable functional group (A) used in the present invention is a (meth) acryloyl group-containing compound usually used in adhesives and paints, and is monofunctional or bifunctional. , Trifunctional and polyfunctional polymerizable monomers, and / or polymerizable oligomers can be used. These can be used alone or as a mixture of two or more.
- (A) component has a preferable (meth) acrylate which has an alkylene oxide structure from a viewpoint that the sclerosis
- the alkylene oxide structure means both an alkylene oxide structure and an alkylene oxide adduct structure. Examples of the alkylene oxide structure include ethylene oxide and propylene oxide.
- Monofunctional monomers include lauryl (meth) acrylate, stearyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) Acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, nonylphenoxyethyl (meth) acrylate , Nonylphenoxytetraethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate Ethoxydiethylene glycol (meth) acrylate, but
- bifunctional monomer examples include 1,3-butylene glycol di (meth) acrylate, 1,4-butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and 1,6-hexane glycol diester.
- trifunctional monomer examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate, epi Examples include chlorohydrin-modified trimethylolpropane tri (meth) acrylate, epichlorohydrin-modified glycerol tri (meth) acrylate, and tris (acryloyloxyethyl) isocyanurate. Among these, curability in antifreeze is excellent. From the viewpoint, ethylene oxide-modified trimethylolpropane tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate and the like can be mentioned .
- polyfunctional monomer examples include ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, alkyl-modified dipentaerythritol pentaacrylate, dipentaerythritol hexa ( And (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate, and the like. These polymerizable monomers can be used alone or as a mixture of two or more.
- the polymerizable monomer can contain a polymerizable oligomer for the purpose of adjusting the viscosity of the anaerobic curable adhesive or adjusting the properties of the cured product.
- a polymerizable oligomer examples include urethane (meth) acrylate having a polybutadiene skeleton, urethane (meth) acrylate having a hydrogenated polybutadiene skeleton, urethane (meth) acrylate having a polycarbonate skeleton, urethane (meth) acrylate having a polyether skeleton, and a polyester skeleton.
- examples include acrylic group-containing polyisobutylene.
- a urethane (meth) acrylate having a polycarbonate skeleton a urethane (meth) acrylate having a polyether skeleton, a urethane (meth) acrylate having a polyester skeleton, and an epoxy (meth) acrylate are preferable, and a polyether skeleton is more preferable.
- Urethane (meth) acrylate and epoxy (meth) acrylate are preferable, and a polyether skeleton is more preferable.
- Urethane (meth) acrylate and epoxy (meth) acrylate These oligomers can be used alone or as a mixture of two or more.
- epoxy (meth) acrylate examples include reaction of bisphenol type epoxy resin, phenol novolac type epoxy resin, epoxy resin such as terminal glycidyl ether of bisphenol A or bisphenol F alkylene oxide adduct and (meth) acrylic acid. And compounds obtained by products (for example, ethoxylated bisphenol A dimethacrylate) and the like. Of these, particularly preferred is a reaction product of an epoxy resin such as terminal glycidyl ether of an alkylene oxide adduct of bisphenol A or bisphenol F with (meth) acrylic acid from the viewpoint of excellent curability in antifreeze. Compound.
- Examples of the component (B) radical polymerization initiator used in the present invention include organic peroxides and photoradical generators.
- organic peroxides are preferred from the viewpoint of anaerobic curability.
- examples of organic peroxides include hydroperoxides such as cumene hydroperoxide, t-butyl hydroperoxide, p-methane hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, and diisopropylbenzene hydroperoxide.
- examples thereof include organic peroxides such as oxides, ketone peroxides, diallyl peroxides, and peroxyesters.
- organic peroxides can be used alone or as a mixture of two or more.
- hydroperoxides are preferably used and cumene hydroperoxide is more preferably used from the viewpoint of long-term storage stability of the reactive and anaerobic curable adhesives.
- the photo radical generator is not particularly limited.
- acetophenone photo radical polymerization initiator benzoin photo radical polymerization initiator, benzophenone photo radical polymerization initiator, thioxanthone photo radical polymerization initiator, acylphosphine
- examples thereof include an oxide photoradical polymerization initiator and a titanocene photoradical polymerization initiator.
- the blending amount of the component (B) is preferably 0.1 to 5 parts by mass, more preferably 0.5 to 1.5 parts by mass with respect to 100 parts by mass of the component (A). In this case, if it is 0.1 mass part or more, a polymerization reaction will fully be produced. If it is 5 mass parts or less, the storage stability of an anaerobic curable resin composition is securable.
- anaerobic polymerization accelerator of the component (C) used in the present invention examples include amine compounds, azole compounds, mercaptan compounds, hydrazine compounds, and derivatives thereof, and these can be used alone or in combination. These can be used alone or as a mixture of two or more. In addition, it is normally used for an anaerobic curable resin composition with (B) component.
- anaerobic curability can be achieved by blending the component (C).
- the amount of component (C) added is preferably 0.1 to 10 parts by weight, more preferably 1 to 3 parts by weight, based on 100 parts by weight of component (A).
- amine compound examples include heterocyclic secondary amines such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine, quinoline, methylquinoline, quinaldine, and quinoxalinephenazine.
- heterocyclic secondary amines such as 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinaldine, quinoline, methylquinoline, quinaldine, and quinoxalinephenazine.
- Heterocyclic tertiary amines, aromatic tertiary amines such as N, N-dimethyl-anisidine, N, N-dimethylaniline and the like can be mentioned.
- azole compound examples include thiazole, isothiazole, thiadiazole, oxazole, isoxazole, oxadiazole, diazole, and triazole. More specifically, saccharin, benzothiazole, 1,2,4-triazole, benzotriazole, hydroxybenzotriazole, benzoxazole, 1,2,3-benzothiadiazole, 3-mercaptobenzotrizole and the like can be mentioned.
- Examples of the mercaptan compound include, but are not limited to, linear mercaptans such as n-dodecyl mercaptan, ethyl mercaptan, and butyl mercaptan.
- hydrazine compound examples include 1-acetyl-2-phenylhydrazine, 1-acetyl-2 (p-tolyl) hydrazine, 1-benzoyl-2-phenylhydrazine, 1- (1 ′, 1 ′, 1′-trifluoro ) Acetyl-2-phenylhydrazine, 1,5-diphenyl-carbohydrazine, 1-formyl-2-phenylhydrazine, 1-acetyl-2- (p-bromophenyl) hydrazine, 1-acetyl-2- (p-nitro) Phenyl) hydrazine, 1-acetyl-2- (2′-phenylethylhydrazine), ethylcarbazate, p-nitrophenylhydrazine, p-trisulfonylhydrazide, and the like, but are not limited thereto.
- an azole compound is preferable from the viewpoint of excellent anaerobic curability. More specifically, saccharin and / or benzothiazole are preferable, and saccharin is more preferable.
- ⁇ (D) component The nonionic surfactant of component (D) used in the present invention, when combined with the other components of the present invention, reduces the cured product of the anaerobic curable resin in the antifreeze liquid, and is also brittle and easily micronized.
- the surfactants are roughly classified into four types: anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants.
- anionic surfactants cationic surfactants
- nonionic surfactants are used. Only found that it has a heterogeneous effect.
- nonionic surfactant examples include a polyoxyalkylene type nonionic surfactant, a polyhydric alcohol type nonionic surfactant, and a sugar type nonionic surfactant, and among them, an anaerobic curable resin in an antifreeze solution.
- a polyoxyalkylene type nonionic surfactant or a polyhydric alcohol type is preferable, and a polyhydric alcohol type is more preferable from the viewpoint that the cured product tends to be small, and is brittle and has the characteristics of being easily formed into fine particles.
- These components may be used alone or in combination.
- polyoxyalkylene type nonionic surfactant examples include polyoxyalkylene alkyl ether and polyoxyalkylene glycol.
- the HLB value is preferably in the range of 6 to 16, more preferably in the range of 7 to 15 because of excellent compatibility with the component (A) of the present invention.
- HLB means hydrophile-lipophile balance (hydrophilic / lipophilic balance) and is an index indicating the balance between hydrophilic groups and lipophilic groups in the molecule of the surfactant.
- the HLB in the present invention is a value calculated by the Griffin method.
- Examples of commercially available polyoxyalkylene alkyl ethers include Neugen XL-80, Neugen XL-160, Neugen TDS-30, Neugen TDS-70, Neugen LF-100X, Neugen LF-202N, Neugen TDX-50, Neugen. And TDX-100D (Daiichi Kogyo Seiyaku Co., Ltd.).
- Examples of commercially available products of polyoxyalkylene glycol include Emanon 1112 and Emanon 3199V (manufactured by Kao Corporation).
- polyhydric alcohol type nonionic surfactant examples include glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, etc.
- the cured product of anaerobic curable resin in antifreeze liquid is weak and immediately Glycerin fatty acid ester is preferable from the viewpoint of being fine.
- the commercially available product examples include tyrazole Z-01, tyrazole Z-02, tyrazole D-818M (manufactured by Taiyo Kagaku Co., Ltd.), and the like.
- sugar-type nonionic surfactant examples include sucrose fatty acid esters and alkylpolyglucosides.
- the amount of component (D) to be added is preferably 0.1 to 50 parts by weight, more preferably 1 to 40 parts by weight, and particularly preferably 3.5 to 100 parts by weight of component (A). ⁇ 35 parts by weight. If it is 50 mass parts or less, high anaerobic curability can be maintained. Moreover, if it is 0.1 weight part or more, the effect of this invention that the hardened
- various elastomers storage stabilizers, antioxidants, light stabilizers, storage stabilizers, heavy metal deactivators, silane coupling agents, tackifiers, plasticizers, as long as the object of the present invention is not impaired.
- Additives such as antifoaming agents, pigments, rust inhibitors, leveling agents, dispersants, rheology modifiers, flame retardants and the like can be used.
- a filler that does not impair storage stability may be added.
- Specific examples include organic powders and inorganic powders.
- the filler for inorganic powder is not particularly limited, but glass, fumed silica, alumina, mica, ceramics, silicone rubber powder, calcium carbonate, aluminum nitride, carbon powder, kaolin clay, dry clay mineral, dry diatomaceous earth, etc. Is mentioned.
- the blending amount of the inorganic powder is preferably about 0.1 to 100 parts by mass with respect to 100 parts by mass of the component (A).
- Fumed silica is blended for the purpose of adjusting the viscosity of the anaerobic curable resin composition or improving the mechanical strength of the cured product.
- fumed silica surface-treated with dimethylsilane, trimethylsilane, alkylsilane, methacryloxysilane, organochlorosilane, polydimethylsiloxane, hexamethyldisilazane, or the like is used.
- Examples of commercially available fumed silica include Aerosil R972, R972V, R972CF, R974, R976, R976S, R9200, RX50, NAX50, NX90, RX200, RX300, R812, R812S, R8200, RY50, NY50, RY200S, RY200, RY300, R104, R106, R202, R805, R816, T805, R711, RM50, R7200, etc. (manufactured by Nippon Aerosil Co., Ltd.) can be mentioned.
- the organic powder filler is not particularly limited, and examples thereof include polyethylene, polypropylene, nylon, crosslinked acrylic, crosslinked polystyrene, polyester, polyvinyl alcohol, polyvinyl butyral, and polycarbonate.
- the blending amount of the organic powder is preferably about 0.1 to 100 parts by mass with respect to 100 parts by mass of the component (A).
- a storage stabilizer may be added to the present invention.
- a radical absorbent such as benzoquinone, hydroquinone, hydroquinone monomethyl ether, a metal chelating agent such as ethylenediaminetetraacetic acid or its 2-sodium salt, oxalic acid, acetylacetone, o-aminophenol, etc. may be added. it can.
- An antioxidant may be added to the present invention.
- the antioxidant include ⁇ -naphthoquinone, 2-methoxy-1,4-naphthoquinone, methyl hydroquinone, hydroquinone, hydroquinone monomethyl ether, mono-t-butyl hydroquinone, 2,5-di-t-butyl hydroquinone, p Quinone compounds such as benzoquinone, 2,5-diphenyl-p-benzoquinone, 2,5-di-t-butyl-p-benzoquinone; phenothiazine, 2,2-methylene-bis (4-methyl-6-t- Butylphenol), catechol, t-butylcatechol, 2-butyl-4-hydroxyanisole, 2,6-di-t-butyl-p-cresol, 2-t-butyl-6- (3-t-butyl-2- Hydroxy-5-methylbenzyl) -4-methylphenyl acrylate, 2- [1- (2-hydroxy 3,5
- a silane coupling agent may be added to the present invention.
- the silane coupling agent is not particularly limited, but ⁇ -chloropropyltrimethoxysilane, octenyltrimethoxysilane, glycidoxyoctyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ - Examples thereof include glycidoxypropyltrimethoxysilane, ⁇ -ureidopropyltriethoxysilane, and p-styryltrimethoxysilane.
- the content of the adhesion-imparting agent is preferably 0.05 to 30 parts by mass, more preferably 0.2 to 10 parts by mass with respect to 100 parts by mass of the component (A).
- the anaerobic curable resin composition of the present invention can be produced by a conventionally known method. For example, by blending predetermined amounts of the components (A) to (D) and using a mixing means such as a mixer, the mixture is preferably mixed at a temperature of 10 to 100 ° C., preferably for 0.1 to 5 hours. Can be manufactured.
- the anaerobic curable resin composition of the present invention is suitably used for bonding and fixing screws, bolts, etc., fixing of fitting parts, bonding, sealing, filling of burrows formed in cast parts, and the like.
- it since it has excellent curability in antifreeze and has properties that the cured product is brittle and easily formed into fine particles, it is extremely effective as a sealant for a welch plug.
- the seal material for a welch plug using the anaerobic curable resin composition the anaerobic sclerosis is excellent even in antifreeze liquid, so that the uncured resin penetrates into the gap between parts such as a water pump valve and a fan and causes a problem. There is nothing.
- the cured product since the cured product is brittle and is easily formed into fine particles, it has an effect that the movement of the valve and the fan is not stopped by pulverizing with a slight stress.
- test methods used in the examples and comparative examples are as follows.
- component (A) of the present invention 70 parts by mass of triethylene glycol dimethacrylate (light acrylate 3EG, manufactured by Kyoeisha Chemical Co., Ltd.) and ethoxylated bisphenol A dimethacrylate (BPE-100, manufactured by Shin-Nakamura Chemical Co., Ltd.) 30 Part by mass; (B) 1 part by mass of cumene hydroperoxide (manufactured by NOF Corporation) as a component; (C) 1 part by mass of saccharin as component, 0.1 part by mass of benzothiazole, An anaerobic curable resin composition of Examples 1 to 9 and Comparative Examples 1 to 6 was added by adding a predetermined amount of the component (D) shown in Table 1 or a comparative component of the component (D) and mixing with a mixer at room temperature for 60 minutes. A product was prepared. All numerical values are expressed in parts by mass.
- d1 Polyoxyalkylene branched decether having an HLB of 13.8 (polyoxyalkylene alkyl ether, Neugen XL-80, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
- d2 polyoxyethylene tridecyl ether having an HLB of 8 (polyoxyalkylene alkyl ether, Neugen TDS-30, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
- d3 polyoxyethylene tridecyl ether having an HLB of 12 (polyoxyalkylene alkyl ether, Neugen TDS-70, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
- d4 polyoxyalkylene alkyl ether having an HLB of 14.5 (polyoxyalkylene alkyl ether, Neugen LF-100X, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
- d5 Polyoxyal
- ⁇ Confirmation of curability in antifreeze 40 parts by mass of 50% antifreeze (Toyota Genuine Super LLC diluted to 50% with pure water) is weighed into a beaker, and 10 parts by mass of each anaerobic curable resin composition thus prepared is added thereto. While stirring at 300 rpm with an air motor stirrer, the temperature is raised to 100 ° C., and after 5 minutes, the presence or absence of curing of the anaerobic curable resin composition is visually confirmed. Those that could be confirmed to be cured were evaluated as “ ⁇ ”, and those that could not be confirmed were evaluated as “ ⁇ ”, and the results are summarized in Table 1.
- the cured product obtained in the curability test in the antifreeze was applied with a load of 60 N with an experimenter's hand using a stick with a sharp tip, and the fragility of the cured product was evaluated based on the following criteria. In addition, among the particles after breaking, the largest size particles were confirmed. The results are shown in Table 1.
- the evaluation result is “ ⁇ ”, it is preferable that the valve of the water pump or the fan is not stopped when used as a sealant for a welch plug.
- Examples 1 to 9 corresponding to the present invention are anaerobic curable resin compositions having excellent curability in antifreeze liquid, and having properties that the cured product is brittle and easy to be finely divided. Recognize.
- Examples 6 to 9 using glycerin fatty acid ester have a small cured product obtained in the antifreeze solution and are particularly preferably used as a sealant for a welch plug.
- Comparative Example 1 is an anaerobic curable resin composition that does not contain a surfactant, but since the size of the cured product in the antifreeze solution is large and the cured product is hard, it is used as a sealant for a Welch plug. If this happens, the water pump valve or fan may stop moving.
- Comparative Examples 2 to 4 are anaerobic curable resin compositions containing an anionic surfactant. The cured product cured in the antifreeze solution is destroyed when force is applied, but the grain size is 1 mm or more. When used as a sealant for a welch plug, there is a risk of stopping the movement of a water pump valve or fan.
- Comparative Examples 5 and 6 are anaerobic curable resin compositions containing a cationic surfactant, but since the cured product cured in the antifreeze solution is hard, when used as a sealant for a welch plug, a water pump valve And there is a risk of stopping the movement of the fan.
- the anaerobic curable resin composition of the present invention is suitably used for bonding and fixing screws, bolts, etc., fixing fitting parts, bonding, sealing, filling burrows formed in cast parts, and the like.
- it since it is excellent in curability in antifreeze, and has a property that the cured product is brittle and easily formed into fine particles, it is industrially useful because it is extremely effective as a sealant for a welch plug.
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Abstract
Description
(A)成分:ラジカル重合性官能基を有する化合物、
(B)成分:ラジカル重合開始剤、
(C)成分:嫌気重合促進剤、
(D)成分:ノニオン系界面活性剤。 Anaerobic curable resin composition containing the following components (A) to (D):
(A) component: a compound having a radical polymerizable functional group,
(B) component: radical polymerization initiator,
(C) component: anaerobic polymerization accelerator,
(D) Component: Nonionic surfactant.
本発明に使用される(A)成分のラジカル重合性官能基を有する化合物とは、接着剤及び塗料等に通常使用されている(メタ)アクリロイル基含有化合物であり、単官能性、二官能性、三官能性及び多官能性の重合性モノマー、ならびに/または重合性オリゴマー等を使用することができる。これらは単独で若しくは二種以上の混合物として用いることができる。なお、(A)成分は、不凍液中での硬化性が優れるという観点から、アルキレンオキサイド構造を有する(メタ)アクリレートが好ましい。また、本発明において、アルキレンオキサイド構造とは、アルキレンオキサイド構造とアルキレンオキサイド付加物の構造との両方を意味する。アルキレンオキサイド構造としては、エチレンオキサイド、プロピレンオキサイド等が挙げられる。 <(A) component>
The compound having a radically polymerizable functional group (A) used in the present invention is a (meth) acryloyl group-containing compound usually used in adhesives and paints, and is monofunctional or bifunctional. , Trifunctional and polyfunctional polymerizable monomers, and / or polymerizable oligomers can be used. These can be used alone or as a mixture of two or more. In addition, (A) component has a preferable (meth) acrylate which has an alkylene oxide structure from a viewpoint that the sclerosis | hardenability in an antifreeze liquid is excellent. In the present invention, the alkylene oxide structure means both an alkylene oxide structure and an alkylene oxide adduct structure. Examples of the alkylene oxide structure include ethylene oxide and propylene oxide.
本発明に用いられる(B)成分ラジカル重合開始剤としては、有機過酸化物や光ラジカル発生剤などが挙げられるが、本発明において有機過酸化物が嫌気硬化性の観点で好ましい。有機過酸化物としては、例えば、クメンハイドロパーオキサイド、t-ブチルハイドロパーオキサイド、p-メタンハイドロパーオキサイド、メチルエチルケトンパーオキサイド、シクロヘキサンパーオキサイド、ジクミルパーオキサイド、ジイソプロピルベンゼンハイドロパーオキサイド等のハイドロパーオキサイド類、その他、ケトンパーオキサイド類、ジアリルパーオキサイド類、パーオキシエステル類等の有機過酸化物等が挙げられる。これらの有機過酸化物は単独で或いは二種以上の混合物として用いることができる。これらのうち、反応性及び嫌気硬化性接着剤の長蔵保存安定性の観点からハイドロパーオキサイド類が好ましく用いられ、クメンハイドロパーオキサイドがより好ましく用いられる。 <(B) component>
Examples of the component (B) radical polymerization initiator used in the present invention include organic peroxides and photoradical generators. In the present invention, organic peroxides are preferred from the viewpoint of anaerobic curability. Examples of organic peroxides include hydroperoxides such as cumene hydroperoxide, t-butyl hydroperoxide, p-methane hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, and diisopropylbenzene hydroperoxide. Examples thereof include organic peroxides such as oxides, ketone peroxides, diallyl peroxides, and peroxyesters. These organic peroxides can be used alone or as a mixture of two or more. Of these, hydroperoxides are preferably used and cumene hydroperoxide is more preferably used from the viewpoint of long-term storage stability of the reactive and anaerobic curable adhesives.
本発明において用いられる(C)成分の嫌気重合促進剤としては、アミン化合物、アゾール化合物、メルカプタン化合物、ヒドラジン化合物、およびこれらの誘導体などが挙げられ、これらを単独あるいは組み合わせて用いることができる。これらは単独で若しくは二種以上の混合物として用いることができる。なお、通常(B)成分と共に嫌気硬化性樹脂組成物に使用される。 <(C) component>
Examples of the anaerobic polymerization accelerator of the component (C) used in the present invention include amine compounds, azole compounds, mercaptan compounds, hydrazine compounds, and derivatives thereof, and these can be used alone or in combination. These can be used alone or as a mixture of two or more. In addition, it is normally used for an anaerobic curable resin composition with (B) component.
本発明に用いられる(D)成分のノニオン系界面活性剤は、本発明のその他成分と組み合わせることにより、不凍液中での嫌気硬化性樹脂の硬化物が小さくなり、しかも脆く、微粒子化しやすいという特性を有する。通常、界面活性剤として、アニオン系界面活性剤、カチオン系界面活性剤、ノニオン系界面活性剤、両イオン界面活性剤の4種類に大別されるが、本発明においては、ノニオン系界面活性剤のみが異質な効果を有することを見出した。前記ノニオン系界面活性剤としては、ポリオキシアルキレン型ノニオン系界面活性剤、多価アルコール型ノニオン系界面活性剤、糖型ノニオン系界面活性剤が挙げられ、中でも不凍液中での嫌気硬化性樹脂の硬化物が小さくなる傾向にあり、しかも脆く、微粒子化しやすいという特性があるという観点でポリオキシアルキレン型ノニオン系界面活性剤または多価アルコール型が好ましく、多価アルコール型がより好ましい。これらの成分は単独でも組み合わせて用いても良い。 <(D) component>
The nonionic surfactant of component (D) used in the present invention, when combined with the other components of the present invention, reduces the cured product of the anaerobic curable resin in the antifreeze liquid, and is also brittle and easily micronized. Have Usually, the surfactants are roughly classified into four types: anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants. In the present invention, nonionic surfactants are used. Only found that it has a heterogeneous effect. Examples of the nonionic surfactant include a polyoxyalkylene type nonionic surfactant, a polyhydric alcohol type nonionic surfactant, and a sugar type nonionic surfactant, and among them, an anaerobic curable resin in an antifreeze solution. A polyoxyalkylene type nonionic surfactant or a polyhydric alcohol type is preferable, and a polyhydric alcohol type is more preferable from the viewpoint that the cured product tends to be small, and is brittle and has the characteristics of being easily formed into fine particles. These components may be used alone or in combination.
本発明の(A)成分として、トリエチレングリコールジメタクリレート(ライトアクリレート3EG、共栄社化学株式会社製)70質量部と、エトキシ化ビスフェノールAジメタクリレート(BPE-100、新中村化学工業株式会社製)30質量部と、
(B)成分としてクメンハイドロパーオキサイド(日本油脂株式会社社製)1質量部と、
(C)成分としてサッカリン1質量部、ベンゾチアゾール0.1質量部と、
表1に示す(D)成分或いは(D)成分の比較成分を所定量で添加し、常温にてミキサーで60分混合し、実施例1~9、比較例1~6の嫌気硬化性樹脂組成物を調製した。数値は全て質量部で表記する。 <Preparation of anaerobic curable resin composition>
As component (A) of the present invention, 70 parts by mass of triethylene glycol dimethacrylate (light acrylate 3EG, manufactured by Kyoeisha Chemical Co., Ltd.) and ethoxylated bisphenol A dimethacrylate (BPE-100, manufactured by Shin-Nakamura Chemical Co., Ltd.) 30 Part by mass;
(B) 1 part by mass of cumene hydroperoxide (manufactured by NOF Corporation) as a component;
(C) 1 part by mass of saccharin as component, 0.1 part by mass of benzothiazole,
An anaerobic curable resin composition of Examples 1 to 9 and Comparative Examples 1 to 6 was added by adding a predetermined amount of the component (D) shown in Table 1 or a comparative component of the component (D) and mixing with a mixer at room temperature for 60 minutes. A product was prepared. All numerical values are expressed in parts by mass.
d1:HLBが13.8であるポリオキシアルキレン分岐デシエーテル(ポリオキシアルキレンアルキルエーテル、ノイゲンXL-80、第一工業製薬株式会社製)
d2:HLBが8であるポリオキシエチレントリデシルエーテル(ポリオキシアルキレンアルキルエーテル、ノイゲンTDS-30、第一工業製薬株式会社製)
d3:HLBが12であるポリオキシエチレントリデシルエーテル(ポリオキシアルキレンアルキルエーテル、ノイゲンTDS-70、第一工業製薬株式会社製)
d4:HLBが14.5であるポリオキシアルキレンアルキルエーテル(ポリオキシアルキレンアルキルエーテル、ノイゲンLF-100X、第一工業製薬株式会社製)
d5:ポリエチレングリコールモノステアレート(エマノーン3199V、花王株式会社製)
d6:グリセリン脂質脂肪酸エステル(チラバゾールW-01、太陽化学株式会社製)
d7:グリセリン脂質脂肪酸エステル(チラバゾールW-02、太陽化学株式会社製)
<(D)成分の比較成分>
d’1:ドデシル硫酸Na(アニオン系界面活性剤、試薬)
d’2:ラウリン酸Na(アニオン系界面活性剤、試薬)
d’3:ポリオキシエチレントリデシルエーテル硫酸Na(アニオン系界面活性剤、ハイテノール330T、第一工業製薬株式会社製)
d’4:ラウリルトリメチルアンモニウムクロライド(カチオン系界面活性剤、コータミン24P、花王株式会社製社製)
d’5:ステアリルトリメチルアンモニウムクロライド(カチオン系界面活性剤、コータミン86W、花王株式会社製社製)
表1の実施例、比較例において使用した試験方法は下記の通りである。 <(D) component>
d1: Polyoxyalkylene branched decether having an HLB of 13.8 (polyoxyalkylene alkyl ether, Neugen XL-80, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
d2: polyoxyethylene tridecyl ether having an HLB of 8 (polyoxyalkylene alkyl ether, Neugen TDS-30, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
d3: polyoxyethylene tridecyl ether having an HLB of 12 (polyoxyalkylene alkyl ether, Neugen TDS-70, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
d4: polyoxyalkylene alkyl ether having an HLB of 14.5 (polyoxyalkylene alkyl ether, Neugen LF-100X, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
d5: Polyethylene glycol monostearate (Emanon 3199V, manufactured by Kao Corporation)
d6: Glycerin lipid fatty acid ester (tyravazole W-01, manufactured by Taiyo Chemical Co., Ltd.)
d7: Glycerin lipid fatty acid ester (tyravazole W-02, manufactured by Taiyo Chemical Co., Ltd.)
<Comparison Component (D)>
d′ 1: sodium dodecyl sulfate (anionic surfactant, reagent)
d'2: Lauric acid Na (anionic surfactant, reagent)
d'3: Polyoxyethylene tridecyl ether sulfate Na (anionic surfactant, Haitenol 330T, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
d′ 4: Lauryltrimethylammonium chloride (cationic surfactant, Coatamine 24P, manufactured by Kao Corporation)
d′ 5: Stearyl trimethyl ammonium chloride (cationic surfactant, Coatamine 86W, manufactured by Kao Corporation)
The test methods used in the examples and comparative examples in Table 1 are as follows.
50%不凍液(トヨタ純正スーパーLLCを純水で50%に希釈したもの)をビーカーに40質量部秤量し、そこに調整した各嫌気硬化性樹脂組成物を10質量部添加する。エアモータ攪拌機で300rpmにて撹拌しながら100℃まで加温し、5分後、嫌気硬化性樹脂組成物の硬化有無を目視で確認する。硬化が確認できたものを「○」、確認できなかったものを「×」として評価し、結果を表1にまとめる。 <Confirmation of curability in antifreeze>
40 parts by mass of 50% antifreeze (Toyota Genuine Super LLC diluted to 50% with pure water) is weighed into a beaker, and 10 parts by mass of each anaerobic curable resin composition thus prepared is added thereto. While stirring at 300 rpm with an air motor stirrer, the temperature is raised to 100 ° C., and after 5 minutes, the presence or absence of curing of the anaerobic curable resin composition is visually confirmed. Those that could be confirmed to be cured were evaluated as “◯”, and those that could not be confirmed were evaluated as “×”, and the results are summarized in Table 1.
不凍液中での硬化性試験にて得られた硬化物の大きさを顕微鏡で確認した。下記基準に基づき評価した。結果を表1に示す。結果は小さいほど好ましい。評価結果が「中」「小」であると、ウェルチプラグ用シール剤として用いた場合、ウォーターポンプの弁やファンの動きを止めることがないので、好ましい。 <Confirmation of size of cured product obtained in antifreeze>
The magnitude | size of the hardened | cured material obtained by the sclerosis | hardenability test in an antifreeze liquid was confirmed with the microscope. Evaluation was based on the following criteria. The results are shown in Table 1. The smaller the result, the better. When the evaluation result is “medium” or “small”, when used as a sealant for a welch plug, the movement of the water pump valve or fan is not stopped, which is preferable.
大:20mm以上
中:5mm以上20mm未満
小:5mm未満
<硬化物の脆さ、微粒子化の確認>
不凍液中での硬化性試験にて得られた硬化物を先端が尖った棒で実験者の手で60Nの荷重を加え、硬化物の壊れやすさを下記基準に基づき評価した。なお、破壊した後の粒子の中、もっともサイズの大きいものを対象に確認した。結果を表1に示す。評価結果が「○」であると、ウェルチプラグ用シール剤として用いた場合、ウォーターポンプの弁やファンの動きを止めることがないので好ましい。
・評価基準
○:力を加えると破壊され、粒子サイズが1mm未満であったもの
△:力を加えると破壊され、粒子サイズが1mm以上であったもの
×:力を加えても破壊されないもの Evaluation criteria Large: 20 mm or more Medium: 5 mm or more and less than 20 mm Small: less than 5 mm <Confirmation of brittleness and micronization of cured product>
The cured product obtained in the curability test in the antifreeze was applied with a load of 60 N with an experimenter's hand using a stick with a sharp tip, and the fragility of the cured product was evaluated based on the following criteria. In addition, among the particles after breaking, the largest size particles were confirmed. The results are shown in Table 1. When the evaluation result is “◯”, it is preferable that the valve of the water pump or the fan is not stopped when used as a sealant for a welch plug.
Evaluation criteria ○: When the force is applied, the particle size is less than 1 mm. Δ: When the force is applied, the particle size is 1 mm or more. ×: When the force is applied, the particle size is not destroyed.
Claims (6)
- 下記の(A)~(D)成分を含有する嫌気硬化性樹脂組成物:
(A)成分:ラジカル重合性官能基を有する化合物、
(B)成分:ラジカル重合開始剤、
(C)成分:嫌気重合促進剤、
(D)成分:ノニオン系界面活性剤。 Anaerobic curable resin composition containing the following components (A) to (D):
(A) component: a compound having a radical polymerizable functional group,
(B) component: radical polymerization initiator,
(C) component: anaerobic polymerization accelerator,
(D) Component: Nonionic surfactant. - 前記(A)成分がアルキレンオキサイド構造を有する(メタ)アクリレートであることを特徴とする請求項1に記載の嫌気硬化性樹脂組成物。 The anaerobic curable resin composition according to claim 1, wherein the component (A) is a (meth) acrylate having an alkylene oxide structure.
- 前記(D)成分が、ポリオキシアルキレン型ノニオン系界面活性剤、多価アルコール型ノニオン系界面活性剤および糖型ノニオン系界面活性剤からなる群から選択される1種以上であることを特徴とする請求項1又は2に記載の嫌気硬化性樹脂組成物。 The component (D) is at least one selected from the group consisting of a polyoxyalkylene type nonionic surfactant, a polyhydric alcohol type nonionic surfactant and a sugar type nonionic surfactant. The anaerobic curable resin composition according to claim 1 or 2.
- 前記(D)成分が、ポリオキシアルキレン型ノニオン系界面活性剤または多価アルコール型ノニオン系界面活性剤であることを特徴とする請求項1~3のいずれか1項に記載の嫌気硬化性樹脂組成物。 The anaerobic curable resin according to any one of claims 1 to 3, wherein the component (D) is a polyoxyalkylene type nonionic surfactant or a polyhydric alcohol type nonionic surfactant. Composition.
- 前記(D)成分が、グリセリン脂肪酸エステルであることを特徴とする請求項1~4のいずれか1項に記載の嫌気硬化性樹脂組成物。 The anaerobic curable resin composition according to any one of claims 1 to 4, wherein the component (D) is a glycerin fatty acid ester.
- 請求項1~5のいずれか1項に記載の嫌気硬化性樹脂組成物を用いたウェルチプラグ用シール剤。 A sealing agent for a welch plug using the anaerobic curable resin composition according to any one of claims 1 to 5.
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WO2023100906A1 (en) * | 2021-11-30 | 2023-06-08 | 東亞合成株式会社 | Anaerobic curing adhesive composition, bonded laminate, motor, and primer composition for anaerobic curing |
WO2023100907A1 (en) * | 2021-11-30 | 2023-06-08 | 東亞合成株式会社 | Anaerobic curing-type adhesive composition, bonded laminate, and motor |
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JP5428860B2 (en) * | 2007-09-25 | 2014-02-26 | 株式会社スリーボンド | Anaerobic curable composition |
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JP2013508476A (en) * | 2009-10-15 | 2013-03-07 | ヘンケル コーポレイション | Anaerobic curable composition |
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WO2023100906A1 (en) * | 2021-11-30 | 2023-06-08 | 東亞合成株式会社 | Anaerobic curing adhesive composition, bonded laminate, motor, and primer composition for anaerobic curing |
WO2023100907A1 (en) * | 2021-11-30 | 2023-06-08 | 東亞合成株式会社 | Anaerobic curing-type adhesive composition, bonded laminate, and motor |
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