CN108779190B - Anaerobically curable resin composition - Google Patents
Anaerobically curable resin composition Download PDFInfo
- Publication number
- CN108779190B CN108779190B CN201780015216.7A CN201780015216A CN108779190B CN 108779190 B CN108779190 B CN 108779190B CN 201780015216 A CN201780015216 A CN 201780015216A CN 108779190 B CN108779190 B CN 108779190B
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- China
- Prior art keywords
- meth
- acrylate
- component
- curable resin
- parts
- 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.)
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 106
- -1 tetrahydrofurfuryl Chemical group 0.000 description 62
- 239000011342 resin composition Substances 0.000 description 28
- 239000007788 liquid Substances 0.000 description 25
- 238000007789 sealing Methods 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000002736 nonionic surfactant Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- 238000007710 freezing Methods 0.000 description 9
- 230000008014 freezing Effects 0.000 description 9
- 150000005215 alkyl ethers Chemical class 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000007870 radical polymerization initiator Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 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 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003093 cationic surfactant Substances 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 230000002528 anti-freeze Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229940106691 bisphenol a Drugs 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
- 125000000524 functional group Chemical group 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 2
- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000000889 atomisation Methods 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
- 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
- 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 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
- 238000000034 method Methods 0.000 description 2
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- PRBBFHSSJFGXJS-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) prop-2-enoate;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O.C=CC(=O)OCC(C)(C)COC(=O)C=C PRBBFHSSJFGXJS-UHFFFAOYSA-N 0.000 description 1
- VYVBVBBLRIGPNM-UHFFFAOYSA-N (3,5-ditert-butylphenyl) propanoate Chemical compound C(CC)(=O)OC1=CC(=CC(=C1)C(C)(C)C)C(C)(C)C VYVBVBBLRIGPNM-UHFFFAOYSA-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
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 description 1
- 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
- RRTJOAHJZQVSSE-UHFFFAOYSA-N 1,3,2-dioxaphosphepine Chemical compound C=1C=COPOC=1 RRTJOAHJZQVSSE-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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 description 1
- QEQMGPQHHWLTHV-UHFFFAOYSA-N 1-sulfanylbenzotriazole Chemical compound C1=CC=C2N(S)N=NC2=C1 QEQMGPQHHWLTHV-UHFFFAOYSA-N 0.000 description 1
- ZZYASVWWDLJXIM-UHFFFAOYSA-N 2,5-di-tert-Butyl-1,4-benzoquinone Chemical compound CC(C)(C)C1=CC(=O)C(C(C)(C)C)=CC1=O ZZYASVWWDLJXIM-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- QYXHDJJYVDLECA-UHFFFAOYSA-N 2,5-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=O)C=C1C1=CC=CC=C1 QYXHDJJYVDLECA-UHFFFAOYSA-N 0.000 description 1
- CSOGFRQNUPVZFS-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)phenol Chemical compound CC1=CC=CC(C=2C(=CC=CC=2)O)=C1C CSOGFRQNUPVZFS-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
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-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
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- NREFJJBCYMZUEK-UHFFFAOYSA-N 2-[2-[4-[2-[4-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]phenyl]propan-2-yl]phenoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOCCOC(=O)C(C)=C)C=C1 NREFJJBCYMZUEK-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
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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
- 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
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229940042596 viscoat Drugs 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Sealing Material Composition (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The purpose of the present invention is to provide an anaerobically curable resin composition having such characteristics that the cured product is relatively brittle and is easily micronized. An anaerobically curable resin composition comprising the following components (A) to (D): component (A): a compound having a radically polymerizable functional group, and a component (B): a radical polymerization initiator, (C) component: an anaerobic polymerization accelerator, (D) component: nonionic surfactants.
Description
Technical Field
The present invention relates to an anaerobic curable resin composition having such characteristics that a cured product is brittle and is easily micronized. The present invention further relates to a wilcoxi sealant using the above-mentioned anaerobic curable resin composition.
Background
The anaerobic curable resin composition is a composition containing a compound having a radically polymerizable functional group such as (meth) acrylate as a main component, and has the following properties: the catalyst is stable in contact with oxygen present in the air, and is kept in a liquid state for a long period of time without gelation, and if oxygen is isolated, radical polymerization proceeds rapidly. The anaerobic curable resin composition is used for: bonding and fixing screws, bolts and the like; fixing, bonding and sealing the embedded component; filling of air holes which may be generated in the cast portion, and the like.
As disclosed in patent document 1, the anaerobic curable resin composition is often used for bonding and sealing between flanges of an engine and a wilcoxi plug of an engine block in an automobile part.
When the wilcoxi plug of the engine block is sealed with the anaerobic curable resin composition, the anaerobic curable resin composition tends to be difficult to cure if eluted into the engine cooling antifreeze fluid. Therefore, there is a risk that the uncured anaerobic curable resin composition eluted into the non-frozen liquid enters into the gap between the valve, blade, and other parts of the water pump and cures, causing a problem. To solve this problem, patent document 2 discloses a (meth) acrylic curable composition containing an anionic surfactant, which has high curability even when dissolved in a non-freezing liquid.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2004-538335
Patent document 2: international publication No. 2012/073684
Disclosure of Invention
However, the present inventors found that: when the curable composition described in patent document 2 is used as an adhesive sealant for wilcoxi, movement of the valve or the vane is prevented by the cured product thereof. As a cause thereof, the following is considered: the curable composition of patent document 2 is a cured product obtained by curing in a non-freezing liquid, and is broken when a load is applied, and the size of particles is 1mm or more, so that the movement of a valve or a vane of a water pump is prevented.
The present invention has been made in view of the above-described circumstances, and an object thereof is to provide an anaerobically curable resin composition having such characteristics that a cured product is brittle and is easily micronized.
The present invention also provides a sealing agent for wilcoxi using the above-mentioned anaerobic curable resin composition.
The present inventors have made intensive studies to achieve the above object, and as a result, have found that an anaerobic curable resin composition and a sealing agent for wilcoxi using the same are involved, and have completed the present invention.
The present invention is as follows.
An anaerobically curable resin composition comprising the following components (A) to (D):
(A) The components are as follows: a compound having a radical polymerizable functional group,
(B) The components are as follows: a radical polymerization initiator,
(C) The components are as follows: anaerobic polymerization accelerator,
(D) The components are as follows: nonionic surfactants.
Detailed Description
The details of the invention are described below.
Component (A)
The compound having a radically polymerizable functional group of the component (a) used in the present invention is a compound having a (meth) acryloyl group which is generally used in adhesives, paints, etc., and a monofunctional, difunctional, trifunctional, polyfunctional polymerizable monomer, and/or polymerizable oligomer may be used. They may be used singly or in the form of a mixture of two or more kinds. From the viewpoint of improving the curability in the antifreeze liquid, the component (a) is preferably a (meth) acrylate having an alkylene oxide structure. In the present invention, the alkylene oxide structure means both of an alkylene oxide structure and a structure of an alkylene oxide adduct. Examples of the alkylene oxide structure include ethylene oxide and propylene oxide.
Examples of the monofunctional monomer 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, butoxyethyl (meth) acrylate, butoxytriethylene glycol (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonylphenylpolypropylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycerin (meth) acrylate, polyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, and modified butyl (meth) acrylate, epichlorohydrin-modified phenoxy (meth) acrylate, ethylene oxide-modified phthalic (meth) acrylate, ethylene oxide-modified succinic (meth) acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, N-dimethylaminoethyl (meth) acrylate, N-diethylaminoethyl (meth) acrylate, morpholino (meth) acrylate, ethylene oxide-modified phosphoric (meth) acrylate, and the like. Among them, from the viewpoint of making the curability in a non-frozen liquid excellent, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, nonylphenoxytetraethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, butoxytriethylene glycol (meth) acrylate, 2-ethylhexyl polyethylene glycol (meth) acrylate, nonylphenylpolypropylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, polyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, ethylene oxide modified phthalic acid (meth) acrylate, ethylene oxide modified succinic acid (meth) acrylate, ethylene oxide modified phosphoric acid (meth) acrylate, and the like are preferable.
Examples of the difunctional monomer include 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, ethylene oxide modified neopentyl glycol di (meth) acrylate, propylene oxide modified neopentyl glycol di (meth) acrylate, hydroxypivalate neopentyl glycol diacrylate, caprolactone modified hydroxypivalate neopentyl glycol diacrylate, neopentyl glycol modified trimethylolpropane di (meth) acrylate, stearic acid modified pentaerythritol di (meth) acrylate, dicyclopentenyl diacrylate, ethylene oxide modified dicyclopentenyl (meth) acrylate, and di (meth) acryl isocyanurate. Among them, 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, ethylene oxide modified neopentyl glycol di (meth) acrylate, propylene oxide modified neopentyl glycol di (meth) acrylate, ethylene oxide modified dicyclopentenyl (meth) acrylate, and the like are preferable from the viewpoint of making the curability in a non-frozen liquid excellent.
Examples of the trifunctional monomer include trimethylol propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethylene oxide modified trimethylol propane tri (meth) acrylate, propylene oxide modified trimethylol propane tri (meth) acrylate, epichlorohydrin modified glycerol tri (meth) acrylate, tris (acryloxyethyl) isocyanurate, and the like, and among these, ethylene oxide modified trimethylol propane tri (meth) acrylate, propylene oxide modified trimethylol propane tri (meth) acrylate, and the like are exemplified from the viewpoint of excellent curability in a non-freezing liquid.
Examples of the polyfunctional monomer include di (trimethylol) propane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol monohydroxy penta (meth) acrylate, alkyl-modified dipentaerythritol pentaacrylate, dipentaerythritol hexa (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate. These polymerizable monomers may be used singly or as a mixture of two or more.
Further, the polymerizable monomer may contain a polymerizable oligomer for the purpose of adjusting the viscosity of the upper anaerobic curable adhesive or adjusting the properties of the cured product thereof. Examples of the polymerizable oligomer 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, urethane (meth) acrylate having a polyester skeleton, urethane (meth) acrylate having a castor oil skeleton, isoprene-based (meth) acrylate, hydrogenated isoprene-based (meth) acrylate, epoxy (meth) acrylate, (meth) acryl-containing acrylic polymer, and (meth) acryl-containing polyisobutylene. The component (a) is preferably a urethane (meth) acrylate of a polycarbonate skeleton, a urethane (meth) acrylate of a polyether skeleton, a urethane (meth) acrylate of a polyester skeleton, or an epoxy (meth) acrylate, and more preferably a urethane (meth) acrylate of a polyether skeleton or an epoxy (meth) acrylate. These oligomers may be used singly or in the form of a mixture of two or more.
Specific examples of the epoxy (meth) acrylate include compounds obtained from reactants of epoxy resins such as terminal glycidyl ethers of alkylene oxide adducts of bisphenol-type epoxy resins, phenol novolac-type epoxy resins, bisphenol-a or bisphenol-F and (meth) acrylic acid (for example, ethoxylated bisphenol-a dimethacrylate), and the like. Among them, compounds obtained from reactants of epoxy resins such as terminal glycidyl ethers of alkylene oxide adducts of bisphenol a or bisphenol F and (meth) acrylic acid and the like are particularly preferable from the viewpoint of excellent curability in a non-freezing liquid.
Examples of the commercial products of the compounds obtained from reactants of epoxy resins such as terminal glycidyl ether of bisphenol A or alkylene oxide adducts of bisphenol F and (meth) acrylic acid include BPE-80-N, BPE-100, BPE-200, BPE-500, BPE-900, BPE-1300N (manufactured by Sanremo chemical Co., ltd.), VISCOAT #700 (manufactured by Osaka organic chemical Co., ltd.), FA-324-A, FA-321M (manufactured by Hitachi chemical Co., ltd.), LIGHT ACRYLATE BP-4EAL, BP-4PA (manufactured by Kabushiki chemical Co., ltd.), and the like, and among these, BPE-100 (manufactured by Sanremo chemical Co., ltd.) is preferably used.
Component (B)
The radical polymerization initiator of component (B) used in the present invention includes an organic peroxide, a photo radical generator, and the like, and in the present invention, an organic peroxide is preferable from the viewpoint of anaerobic curability. Examples of the organic peroxide include: hydroperoxides such as cumene hydroperoxide, tert-butyl hydroperoxide, p-methane hydroperoxide, methyl ethyl ketone peroxide, cyclohexane peroxide, dicumyl peroxide, and diisopropylbenzene hydroperoxide; organic peroxides such as peroxyketones, diallyl peroxides, and peroxyesters. These organic peroxides may be used singly or in the form of a mixture of two or more kinds. Among them, hydrogen peroxide is preferably used, and cumene hydroperoxide is more preferably used, from the viewpoint of long-term storage stability of the reactive and anaerobic curable adhesive.
Examples of the photo-radical generator include, but are not particularly limited to, acetophenone-based photo-radical polymerization initiators, benzoin-based photo-radical polymerization initiators, benzophenone-based photo-radical polymerization initiators, thioxanthone-based photo-radical polymerization initiators, acylphosphine oxide-based photo-radical polymerization initiators, and titanocene-based photo-radical polymerization initiators.
The amount of the component (B) to be blended is preferably 0.1 to 5 parts by mass, more preferably 0.5 to 1.5 parts by mass, based on 100 parts by mass of the component (A). At this time, if it is 0.1 part by mass or more, the polymerization reaction sufficiently occurs. If it is 5 parts by mass or less, the storage stability of the anaerobic curable resin composition can be ensured.
Component (C)
Examples of the anaerobic polymerization accelerator for the component (C) used in the present invention include amine compounds, azole compounds, thiol compounds, hydrazine compounds and derivatives thereof, and these may be used alone or in combination. They may be used singly or in the form of a mixture of two or more kinds. The component (B) is usually used in an anaerobically curable resin composition.
By blending this component (C), good anaerobic curability can be achieved. (C) The amount of the component (A) to be added is preferably 0.1 to 10 parts by mass, more preferably 1 to 3 parts by mass, based on 100 parts by mass of the component (A).
Examples of the amine compound include: heterocyclic secondary amines such as 1,2,3, 4-tetrahydroquinoline and 1,2,3, 4-tetrahydroquinaldine; heterocyclic tertiary amines such as quinoline, methylquinoline, quinaldine, quinoxaline phenazine, and the like; and aromatic tertiary amines such as N, N-dimethyl-methoxyaniline and N, N-dimethylaniline.
Examples of the azole compound 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-mercaptobenzotriazole, and the like can be cited.
Examples of the thiol compound include straight-chain thiols such as n-dodecyl thiol, ethyl thiol, and butyl thiol, but are not limited thereto.
Examples of the hydrazine compound 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-carbohydrazide, 1-formyl-2-phenylhydrazine, 1-acetyl-2- (p-bromophenyl) hydrazine, 1-acetyl-2- (p-nitrophenyl) hydrazine, 1-acetyl-2- (2' -phenylethylhydrazine), ethyl hydrazinoformate, p-nitrophenylhydrazine, and p-trisulfonylhydrazine, but are not limited thereto.
Among the components (C), the azole compound is preferable from the viewpoint of excellent anaerobic curability. More specifically, saccharin and/or benzothiazole are preferable, and saccharin is more preferable.
Component (D)
The nonionic surfactant of component (D) used in the present invention has the characteristics of making the cured product of the anaerobic curable resin in the non-frozen liquid small, brittle and easily micronized by combining with other components of the present invention. Generally, surfactants are classified into four types, i.e., anionic surfactants, cationic surfactants, nonionic surfactants, and amphoteric surfactants, but in the present invention, only nonionic surfactants have been found to have a heterogeneous effect. Among these nonionic surfactants, polyoxyalkylene nonionic surfactants, polyhydric alcohol nonionic surfactants, and sugar nonionic surfactants are preferable, and polyhydric alcohol nonionic surfactants are more preferable from the viewpoint of having a tendency to reduce the cured product of the anaerobic curable resin in the antifreeze liquid, being relatively brittle, and having characteristics such as easy atomization. These components may be used alone or in combination.
Examples of the polyoxyalkylene nonionic surfactant include polyoxyalkylene alkyl ether and polyoxyalkylene glycol. The polyoxyalkylene alkyl ether preferably has an HLB value in the range of 6 to 16, more preferably in the range of 7 to 15, from the viewpoint of excellent compatibility with the component (A) of the present invention. HLB is Hydrophile-lipophile balance (hydrophilic-lipophilic balance), which is an index indicating the balance of hydrophilic groups and lipophilic groups in the molecule of a surfactant. In the present invention, HLB is a value calculated by Griffin method. Examples of the commercially available polyoxyalkylene alkyl ether include Noigen XL-80, noigen XL-160, noigen TDS-30, noigen TDS-70, noigen LF-100X, noigen LF-202N, noigen TDX-50, noigen TDX-100D (manufactured by first Industrial pharmaceutical Co., ltd.). Examples of the commercial products of polyoxyalkylene glycol include Emanon 1112 and Emanon 3199V (manufactured by Kagaku Co., ltd.).
Among these, glycerin fatty acid esters are preferable from the viewpoint of making the cured product of the anaerobic curable resin in the non-frozen liquid weak and immediately finer. As the commercial products, chirabasol W-01, chirabasol W-02, chirabasol D-818M (manufactured by Sun chemical Co., ltd.) and the like can be mentioned.
Examples of the sugar-based nonionic surfactant include sucrose fatty acid esters and alkyl polyglucosides.
(D) The amount of the component (A) to be added is preferably 0.1 to 50 parts by weight, more preferably 1 to 40 parts by weight, particularly preferably 3.5 to 35 parts by weight, based on 100 parts by weight of the component (A). If it is 50 parts by mass or less, the high anaerobic curability can be maintained. If the amount is 0.1 part by weight or more, the effect of the present invention is obtained that the cured product cured in the non-frozen liquid is brittle and is easily micronized.
For the present invention, additives such as various elastomers, storage stabilizers, antioxidants, light stabilizers, storage stabilizers, heavy metal deactivators, silane coupling agents, tackifiers, plasticizers, antifoaming agents, pigments, rust inhibitors, leveling agents, dispersants, rheology modifiers, flame retardants and the like may be used within a range not impairing the object of the present invention.
In the present invention, a filler may be added to the extent that the storage stability is not impaired for the purpose of improving the elastic modulus, flowability, and the like of the cured product. Specifically, organic powder, inorganic powder, and the like are exemplified.
The filler for the inorganic powder is not particularly limited, and examples thereof include glass, fumed silica, alumina, mica, ceramics, silicone rubber powder, calcium carbonate, aluminum nitride, carbon powder, kaolin clay, dry clay minerals, dry diatomaceous earth, and the like. The amount of the inorganic powder to be blended is preferably about 0.1 to 100 parts by mass based on 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. Preferably, fumed silica surface-treated with dimethylsilane, trimethylsilane, alkylsilane, methacryloxysilane, organochlorosilane, polydimethylsiloxane, hexamethyldisilazane, or the like is used. Examples of the commercial fumed silica include Aerosil R972, R972V, R972CF, R974, R976S, R9200, RX50, NAX, NX90, RX200, RX300, R812S, R8200, RY50, NY50, RY200S, RY200, RY300, R104, R106, R202, R805, R816, T805, R711, RM50, R7200, and the like (manufactured by japan Aerosil corporation).
The filler for the organic powder is not particularly limited, and examples thereof include polyethylene, polypropylene, nylon, crosslinked acrylic acid, crosslinked polystyrene, polyester, polyvinyl alcohol, polyvinyl butyral, and polycarbonate. The amount of the organic powder to be blended is preferably about 0.1 to 100 parts by mass based on 100 parts by mass of the component (A).
For the present invention, a storage stabilizer may be added. As a storage stabilizer, it is also possible to add: radical absorbers such as benzoquinone, hydroquinone, and hydroquinone monomethyl ether; metal chelate agents such as ethylenediamine tetraacetic acid or ethylenediamine tetraacetic acid-2-sodium salt, oxalic acid, acetylacetone, and o-aminophenol.
For the present invention, an antioxidant may be added. Examples of the antioxidant include: quinone compounds such as beta-naphthoquinone, 2-methoxy-1, 4-naphthoquinone, methyl hydroquinone, hydroquinone monomethyl ether, mono-t-butyl hydroquinone, 2, 5-di-t-butyl hydroquinone, p-benzoquinone, 2, 5-diphenyl-p-benzoquinone, and 2, 5-di-t-butyl-p-benzoquinone; phenothiazine, 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-di-t-pentylphenyl) ethyl ] -4, 6-di-t-pentylphenyl acrylate, 4 '-butylidenebis (6-t-butyl-3-methylphenol), 4' -thiobis (6-t-butyl-3-methylphenol), 3, 9-bis [ 2- [ 3- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy ] -1, 1-dimethylethyl ] -2,4,8, 10-tetraoxaspiro [ 5,5 ] undecane, pentaerythritol tetrakis [ 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ], bis [ 3- (3, 5-di-t-butylphenyl) ethylene ] -3- (3-t-butylphenyl) propionate, N-bis [ 3, 5-di-t-butylphenyl ] propionate, N '-hexane-1, 6-diylbis [ 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionamide ], C7-C9 side chain alkyl 3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenylpropionate, 2, 4-dimethyl-6- (1-methylpentadecyl) phenol, diethyl- [ 3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] phosphonate, 3',3", 5',5" -hexatertiary butyl-a, a', a' - (mesitylene-2, 4, 6-tolyl) tri-p-cresol, diethyl bis- [ 3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] phosphonate calcium, 4, 6-bis (octylthiomethyl) o-cresol, ethylene bis (oxyethylene) bis [ 3- (5-tert-butyl-4-hydroxy-m-tolyl) propionate ], hexamethylenebis [ 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 1,3, 5-tris- [ 4-tert-butyl-3-hydroxy-2, 6-xylyl) methyl ] -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, N-phenylaniline and 2, 6-t-butyl-4-hydroxybenzyl) propionate, 1,3, 5-triazine-2, 6- (2, 6-t-butyl-amino) phenol, 4-tris (1H, 3H, 5-tris (4-xylyl) phenol, 4-tris (2, 6-t-butyl-4-hydroxyphenyl) phenol, and the like; phosphorus compounds such as tris (2, 4-di-t-butylphenyl) phosphite, tris [ 2- [ 2,4,8, 10-tetra-t-butyldibenzo [ d, f ] [ 1,3,2 ] dioxaphosphepin (dioxaphosphorinane) -6-yl ] ethyl ] amine, bis (2, 4-di-t-butylphenyl) pentaerythritol diphosphite, bis [ 2, 4-bis (1, 1-dimethylethyl) -6-methylphenyl ] ethyl phosphite, tetrakis (2, 4-di-t-butylphenyl) [ 1, 1-diphenyl ] -4,4' -diyl bisphosphonate, 6- [ 3- (3-t-butyl-4-hydroxy-5-methylphenyl) propoxy ] -2,4,8, 10-tetra-t-butyldibenzo [ d, f ] [ 1,3,2 ] dioxaphosphepin; thio compounds such as dilauryl 3,3' -thiodipropionate, dimyristyl 3,3' -thiodipropionate, distearyl 3,3' -thiodipropionate, pentaerythritol tetrakis (3-laurylthiopropionate), and 2-mercaptobenzimidazole; amine compounds such as phenothiazine; a lactone compound; vitamin E compounds, and the like. Among them, a phenol compound is preferable.
For the present invention, a silane coupling agent may be added. The silane coupling agent is not particularly limited, but examples thereof include gamma-chloropropyl trimethoxysilane, octenyl trimethoxysilane, glycidoxy octyl trimethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyl trimethoxysilane, gamma-glycidoxy propyl trimethoxysilane, gamma-ureido propyl triethoxysilane, p-styryl trimethoxysilane, and the like. 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, based on 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, the composition can be produced by mixing the components (A) to (D) in a predetermined amount by mixing means such as a mixer at a temperature of preferably 10 to 100℃for preferably 0.1 to 5 hours.
The anaerobic curable resin composition of the present invention is suitably used for: bonding and fixing screws, bolts and the like; fixing, bonding and sealing the embedded component; filling of air holes generated in the cast portion, and the like. In particular, the composition is excellent in curability in a non-freezing liquid, and the cured product is brittle and is easily micronized, and therefore is extremely effective as a sealing agent for Wilki. According to the wilkins sealant using the above-mentioned anaerobic curable resin composition, the anaerobic curability is excellent even in the non-frozen liquid, and therefore, the uncured resin is not allowed to enter the gap of the valve, the blade, or the like of the water pump and cure, and thus, the problem is not caused. Further, the following effects are obtained: since the cured product is brittle and is easily micronized, the pulverization is performed under a small stress, and the movement of the valve or the vane is not prevented.
Examples
The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
The test methods used in the examples and comparative examples are as follows.
Preparation of anaerobic curable resin composition
And (3) adding: 70 parts by mass of triethylene glycol dimethacrylate (LIGHT ACRYLATE EG, manufactured by Kabushiki Kaisha chemical Co., ltd.) and 30 parts by mass of ethoxylated bisphenol A dimethacrylate (BPE-100, manufactured by Xinzhou Chemie Co., ltd.);
1 part by mass of cumene hydroperoxide (manufactured by Japanese fat & oil Co., ltd.) as the component (B);
1 part by mass of saccharin as the component (C), and 0.1 part by mass of benzothiazole; and
a predetermined amount of the component (D) shown in Table 1 or a comparative component of the component (D),
the anaerobic curable resin compositions of examples 1 to 9 and comparative examples 1 to 6 were prepared by mixing them with a mixer at room temperature for 60 minutes. The values are all expressed in parts by mass.
Component (D)
d1: polyoxyalkylene branched decyl ether (polyoxyalkylene alkyl ether, noigen XL-80, manufactured by first industry pharmaceutical Co., ltd.) having HLB of 13.8
d2: polyoxyethylene tridecyl ether having HLB of 8 (polyoxyalkylene alkyl ether, noigen TDS-30, manufactured by first industry pharmaceutical Co., ltd.)
d3: polyoxyethylene tridecyl ether having HLB of 12 (polyoxyalkylene alkyl ether, noigen TDS-70, manufactured by first industry pharmaceutical Co., ltd.)
d4: polyoxyalkylene alkyl ether having HLB of 14.5 (polyoxyalkylene alkyl ether, noigen LF-100X, manufactured by first industry Co., ltd.)
d5: polyethylene glycol monostearate (Emanon 3199V, manufactured by Kagaku Co., ltd.)
d6: glycerolipid fatty acid ester (Chirabasol W-01, manufactured by Sun chemical Co., ltd.)
d7: glycerolipid fatty acid ester (Chirabasol W-02, manufactured by Sun chemical Co., ltd.)
Comparative component of component (D)
d'1: dodecyl sulfate Na (anionic surfactant, reagent)
d'2: lauric acid Na (anionic surfactant, reagent)
d'3: polyoxyethylene tridecyl ether sulfate Na (anionic surfactant, hitenol 330T, manufactured by first Industrial pharmaceutical Co., ltd.)
d'4: lauryl trimethyl ammonium chloride (cationic surfactant, QUARTAMIN 24P, manufactured by Kagaku Co., ltd.)
d'5: stearyl trimethyl ammonium chloride (cationic surfactant, QUARTAMIN 86W, manufactured by Kagaku Co., ltd.)
The test methods used in the examples and comparative examples of table 1 are as follows.
< confirmation of curability in non-frozen liquid >
40 parts by mass of a 50% non-frozen solution (a solution obtained by diluting TOYOTA pure SUPER LLC with pure water to 50%) was weighed in a beaker, and 10 parts by mass of each of the prepared anaerobic curable resin compositions was added thereto. While stirring at 300rpm with a pneumatic motor stirrer, the temperature was raised to 100℃for 5 minutes, and then the presence or absence of curing of the anaerobic curable resin composition was visually confirmed. The results are shown in table 1, in which the cases where curing was confirmed were evaluated as "o", the cases where curing was not confirmed were evaluated as "x".
< confirmation of size of cured product obtained in unfrozen liquid >
The size of the cured product obtained by the curability test in the non-frozen liquid was confirmed by a microscope. The evaluation was performed based on the following criteria. The results are shown in Table 1. The smaller the result, the more preferable. If the evaluation result is "medium" or "small", the movement of the valve or vane of the water pump is not prevented when the water pump is used as a sealing agent for a wilcoxi plug, and therefore, the water pump is preferable.
Evaluation criterion
Large: 20mm or more
In (a): more than 5mm but less than 20mm
The size is small: less than 5mm
< confirmation of brittleness and micronization of cured product >
The experimenter applied a 60N load to the cured product obtained by the curability test in a non-freezing liquid with a hand-held sharp-tipped rod, and evaluated the destructibility of the cured product based on the following criteria. Among the particles after the fracture, the particle having the largest size was confirmed as the object. The results are shown in Table 1. If the evaluation result is "o", the movement of the valve or the vane of the water pump is not prevented when the sealing agent is used as a sealing agent for wilcoxi, and is preferable.
Evaluation criterion
O: if a force is applied, the particle is broken and the particle size is less than 1mm
Delta: if a force is applied, the particle is broken and the particle size is 1mm or more
X: even if the applied force is not destroyed
TABLE 1
From table 1, examples 1 to 9 belonging to the present invention are anaerobic curable resin compositions having the characteristics of excellent curability in a non-freezing liquid, and brittle cured products and easy atomization. Among them, examples 6 to 9 using glycerin fatty acid ester have small cured products obtained in a non-frozen liquid, and are particularly suitable as a sealing agent for wilcoxi.
In addition, comparative example 1 is an anaerobic curable resin composition containing no surfactant, but the cured product after curing in a non-frozen liquid is large in size and hard, so that when used as a sealing agent for wilkins, there is a risk of preventing movement of a valve or a vane of a water pump. Comparative examples 2 to 4 are anaerobic curable resin compositions containing an anionic surfactant, but the cured product after curing in a non-freezing liquid is broken by application of force, and the particle size is 1mm or more, and when used as a sealing agent for a wilcoxib, there is a risk of preventing movement of a valve or a vane of a water pump. Comparative examples 5 and 6 are anaerobic curable resin compositions containing a cationic surfactant, and since the cured product after curing in a non-freezing liquid is hard, there is a risk of preventing movement of a valve or a vane of a water pump when used as a sealing agent for a wilcoxib.
Industrial applicability
The anaerobic curable resin composition of the present invention is suitably used for: bonding and fixing screws, bolts and the like; fixing, bonding and sealing the embedded component; filling of air holes generated in the cast member, and the like. In particular, the present invention is industrially useful because it has excellent curability in a non-frozen liquid, and because the cured product is brittle and is easily micronized, it is extremely effective as a sealing agent for wilcoxi.
Claims (5)
1. An anaerobically curable resin composition comprising the following components (A) to (D):
(A) The components are as follows: triethylene glycol dimethacrylate, ethoxylated bisphenol A dimethacrylate,
(B) The components are as follows: radical polymerization initiator of hydrogen peroxide,
(C) The components are as follows: saccharin and/or benzothiazole,
(D) The components are as follows: a glycerin fatty acid ester,
(B) The amount of the component (A) to be blended is 0.1 to 5 parts by mass based on 100 parts by mass of the component (A), the amount of the component (C) to be added is 0.1 to 10 parts by mass based on 100 parts by mass of the component (A), and the amount of the component (D) to be added is 3.5 to 35 parts by mass based on 100 parts by mass of the component (A).
2. The anaerobic curable resin composition according to claim 1, wherein the component (B) contains cumene hydroperoxide.
3. The anaerobic curable resin composition according to claim 1, wherein the component (C) contains saccharin and benzothiazole.
4. The anaerobic curable resin composition according to claim 1, wherein the blending amount of the component (B) is 0.5 to 5 parts by mass based on 100 parts by mass of the component (A).
5. The anaerobic curable resin composition according to claim 1, wherein the amount of component (C) is 1 to 3 parts by mass per 100 parts by mass of component (A).
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| JP2016046481 | 2016-03-10 | ||
| JP2016-046481 | 2016-03-10 | ||
| PCT/JP2017/007051 WO2017154616A1 (en) | 2016-03-10 | 2017-02-24 | Anaerobic curable resin composition and sealant for welch plug in which same is used |
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| CN108779190B true CN108779190B (en) | 2024-02-09 |
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| US20250026967A1 (en) * | 2021-11-30 | 2025-01-23 | Toagosei Co., Ltd. | Anaerobic curing adhesive composition, bonded laminated body, and motor |
| CN118355085A (en) * | 2021-11-30 | 2024-07-16 | 东亚合成株式会社 | Anaerobic curing adhesive composition, adhesive laminate, motor, and anaerobic curing primer composition |
| WO2025022871A1 (en) * | 2023-07-21 | 2025-01-30 | ソマール株式会社 | Anaerobic adhesive, cured product, bonded stack, and motor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6447868B2 (en) * | 2014-12-22 | 2019-01-09 | 株式会社スリーボンド | Anaerobic curable adhesive |
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2017
- 2017-02-24 CN CN201780015216.7A patent/CN108779190B/en active Active
- 2017-02-24 JP JP2018504369A patent/JP6892607B2/en active Active
- 2017-02-24 WO PCT/JP2017/007051 patent/WO2017154616A1/en active Application Filing
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| JPS641779A (en) * | 1987-06-24 | 1989-01-06 | Toagosei Chem Ind Co Ltd | Adhesive composition |
| JPH0339378A (en) * | 1989-07-05 | 1991-02-20 | Hitachi Chem Co Ltd | Adhesive composition, method for fixing electronic component to print substrate and production of integrated circuit board |
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| WO2017154616A1 (en) | 2017-09-14 |
| JP6892607B2 (en) | 2021-06-23 |
| JPWO2017154616A1 (en) | 2019-01-17 |
| CN108779190A (en) | 2018-11-09 |
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