CN108779190A - Anaerobically curable resin combination and the strange plug sealant of Weir using it - Google Patents
Anaerobically curable resin combination and the strange plug sealant of Weir using it Download PDFInfo
- Publication number
- CN108779190A CN108779190A CN201780015216.7A CN201780015216A CN108779190A CN 108779190 A CN108779190 A CN 108779190A CN 201780015216 A CN201780015216 A CN 201780015216A CN 108779190 A CN108779190 A CN 108779190A
- Authority
- CN
- China
- Prior art keywords
- methyl
- acrylate
- ingredient
- curable resin
- anaerobically curable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920005989 resin Polymers 0.000 title claims abstract description 38
- 239000011347 resin Substances 0.000 title claims abstract description 38
- 239000000565 sealant Substances 0.000 title claims description 15
- 239000004615 ingredient Substances 0.000 claims abstract description 53
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 8
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 6
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 50
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 30
- -1 (methyl) acryloyl group Chemical group 0.000 description 63
- 239000000243 solution Substances 0.000 description 27
- 230000008014 freezing Effects 0.000 description 26
- 238000007710 freezing Methods 0.000 description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 150000005215 alkyl ethers Chemical class 0.000 description 8
- 238000007711 solidification Methods 0.000 description 8
- 230000008023 solidification Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- 230000004048 modification Effects 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
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- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 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 6
- 230000000052 comparative effect Effects 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 5
- BOSPHQRXWAPYSU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;methyl prop-2-enoate Chemical compound COC(=O)C=C.OCCOCCO BOSPHQRXWAPYSU-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000012790 confirmation Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 239000007767 bonding agent Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002091 cationic group Chemical group 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
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 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 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 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
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- CSHOPPGMNYULAD-UHFFFAOYSA-N 1-tridecoxytridecane Chemical compound CCCCCCCCCCCCCOCCCCCCCCCCCCC CSHOPPGMNYULAD-UHFFFAOYSA-N 0.000 description 2
- KLGDEHQTPPRXHJ-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;methyl prop-2-enoate Chemical compound COC(=O)C=C.CC(O)COC(C)CO KLGDEHQTPPRXHJ-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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical class CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- AXPZIVKEZRHGAS-UHFFFAOYSA-N 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1OC(=O)C(CC=2C=CC=CC=2)C1 AXPZIVKEZRHGAS-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
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- 230000000996 additive effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 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
- 210000000988 bone and bone Anatomy 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 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
- 229960001484 edetic acid Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012458 free base Substances 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
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- FLUHOKZCSIYKQX-UHFFFAOYSA-N methyl prop-2-enoate phosphoric acid Chemical class COC(C=C)=O.P(=O)(O)(O)O FLUHOKZCSIYKQX-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
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- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 1
- ISNKSXRJJVWFIL-UHFFFAOYSA-N (sulfonylamino)amine Chemical class NN=S(=O)=O ISNKSXRJJVWFIL-UHFFFAOYSA-N 0.000 description 1
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- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-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
- QEQMGPQHHWLTHV-UHFFFAOYSA-N 1-sulfanylbenzotriazole Chemical class C1=CC=C2N(S)N=NC2=C1 QEQMGPQHHWLTHV-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
- IRHICGGRMJVIOW-UHFFFAOYSA-N 2-(2,4,6-trioxo-1,3,5-triazinan-1-yl)ethyl prop-2-enoate Chemical class C=CC(=O)OCCN1C(=O)NC(=O)NC1=O IRHICGGRMJVIOW-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
- AOARLESXCKBSKT-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol methyl prop-2-enoate Chemical compound C(C=C)(=O)OC.C(COCCOCCOCCO)O AOARLESXCKBSKT-UHFFFAOYSA-N 0.000 description 1
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- 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
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- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical class CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- KHMMKULJQXMDPR-UHFFFAOYSA-N 3-(1-carboxyicosan-2-ylsulfanyl)henicosanoic acid Chemical class CCCCCCCCCCCCCCCCCCC(CC(O)=O)SC(CC(O)=O)CCCCCCCCCCCCCCCCCC KHMMKULJQXMDPR-UHFFFAOYSA-N 0.000 description 1
- UNIYDALVXFPINL-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propylsilicon Chemical compound CC(=C)C(=O)OCCC[Si] UNIYDALVXFPINL-UHFFFAOYSA-N 0.000 description 1
- QXDPCGKKEULHIW-UHFFFAOYSA-N 3-prop-2-enylperoxyprop-1-ene Chemical compound C=CCOOCC=C QXDPCGKKEULHIW-UHFFFAOYSA-N 0.000 description 1
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- 239000003063 flame retardant Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical class OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- RLFXWALMKAWBBF-UHFFFAOYSA-N methyl prop-2-enoate propane-1,2,3-triol Chemical compound C(C=C)(=O)OC.OCC(O)CO RLFXWALMKAWBBF-UHFFFAOYSA-N 0.000 description 1
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- CKLPECFHCLIYKN-UHFFFAOYSA-N n'-phenylbenzohydrazide Chemical class C=1C=CC=CC=1C(=O)NNC1=CC=CC=C1 CKLPECFHCLIYKN-UHFFFAOYSA-N 0.000 description 1
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- 229920001778 nylon Polymers 0.000 description 1
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- 239000003921 oil Substances 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
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- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- LPBNNQBYFCZCTA-UHFFFAOYSA-N sulfuric acid;1-tridecoxytridecane Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCOCCCCCCCCCCCCC LPBNNQBYFCZCTA-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
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- 230000000007 visual effect Effects 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 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 anaerobically curable resin combinations more crisp with solidfied material, being easy characteristic as micronized.A kind of anaerobically curable resin combination contains following (A)~(D) ingredients：(A) ingredient：Compound, (B) ingredient with free-radical polymerised functional group：Radical polymerization initiator, (C) ingredient：Anaerobism polymerization accelerant, (D) ingredient：Nonionic surfactants.
Description
Technical field
The present invention relates to anaerobically curable resin combinations more crisp with solidfied material, being easy characteristic as micronized.
In turn, the present invention relates to used the strange plug sealant of the Weir of above-mentioned anaerobically curable resin combination.
Background technology
Anaerobically curable resin combination is the chemical combination for having free-radical polymerised functional group with (methyl) acrylate etc.
Composition of the object as principal component, has the following properties that：It is relatively stable during being contacted with existing oxygen in air, it will not
Gelation etc. and kept for a long time with liquid state, if isolating oxygen, hastily carry out Raolical polymerizable.Utilize such property
Matter and above-mentioned anaerobically curable resin combination is used for：Screw, bolt etc. are bonded, fix；Gomphosis part it is fixed, viscous
It connects, seal；The filling etc. for the stomata that may be generated in cast part.
In addition, as shown in Patent Document 1 like that, anaerobically curable resin combination is chiefly used in engine in automobile component
Flange between, the adhering and sealing etc. very filled in of the Weir of cluster engine.
In the case where being sealed the strange plug of the Weir of cluster engine using anaerobically curable resin combination, if anaerobism
In hardening resin composition dissolution to engine cool non-freezing solution, then exists and be difficult to cured tendency.Accordingly, there exist dissolutions
The gap of the components such as valve or the blade of water pump is entered to the uncured anaerobically curable resin combination in non-freezing solution and is consolidated
Change and cause the risk of unfavorable condition.For the problem, Patent Document 2 discloses to include anionic surfactant
(methyl) acrylic acid series solidification compound being characterized, even if in solidification compound dissolution to non-freezing solution, it may have high
Curability.
Existing technical literature
Patent document
Patent document 1：Japanese Unexamined Patent Application Publication 2004-538335 bulletins
Patent document 2：No. 2012/073684 bulletin of International Publication No.
Invention content
However, the inventors of the present invention have found：What is very filled in as Weir using the solidification compound described in patent document 2
In the case of adhesive sealant, the movement of valve or blade is prevented using its solidfied material.As its reason, it is believed that as follows：Patent
Solidfied material made of the solidification compound of document 2 cures in non-freezing solution is destroyed when applying load, and due to particle
Size be 1mm or more, therefore cause prevent water pump valve or blade movement.
The present invention is the invention completed in view of above-mentioned situation, and its purpose is to provide more crisp with solidfied material, easy
The anaerobically curable resin combination of characteristic as micronized.
The present invention also aims to provide that the Weir very plug of above-mentioned anaerobically curable resin combination has been used to seal
Agent.
The inventors of the present invention have made intensive studies in order to achieve the above objectives, as a result, it has been found that with anaerobically curable resin group
It closes object and uses its Weir very related way of plug sealant, so that complete the present invention.
The present invention is as shown below.
A kind of anaerobically curable resin combination contains following (A)~(D) ingredients：
(A) ingredient：Compound with free-radical polymerised functional group,
(B) ingredient：Radical polymerization initiator,
(C) ingredient：Anaerobism polymerization accelerant,
(D) ingredient：Nonionic surfactants.
Specific implementation mode
The details of invention is illustrated below.
< (A) ingredients >
The compound with free-radical polymerised functional group of (A) ingredient used in the present invention is in bonding agent and painting
The commonly used compound containing (methyl) acryloyl group in material etc. can use mono-functional, two functionalities, trifunctional
Property and multi-functional polymerizable monomer, and/or polyreactive oligomers etc..They can be used alone or with two or more
The form of mixture uses.It is explained, from keeping the excellent curability viewpoint in non-freezing solution, (A) ingredient preferred
(methyl) acrylate with oligoalkylene oxide structure.In addition, in the present invention, oligoalkylene oxide structure refers to oligoalkylene oxide structure and epoxy
Both structures of alkane addition product.As oligoalkylene oxide structure, ethylene oxide, propylene oxide etc. can be enumerated.
As mono-functional's monomer, (methyl) lauryl acrylate, (methyl) stearyl acrylate, (methyl) third can be enumerated
Olefin(e) acid tetrahydrochysene chaff ester, caprolactone modification (methyl) tetrahydrofurfuryl acrylate, (methyl) cyclohexyl acrylate, (methyl) acrylic acid two
Pentamethylene ester, (methyl) isobornyl acrylate, (methyl) benzyl acrylate, (methyl) phenyl acrylate, (methyl) acrylic acid
Phenoxy ethyl, phenoxy group diethylene glycol (methyl) acrylate, phenoxy group tetraethylene glycol (methyl) acrylate, nonyl benzene oxygen
Base ethyl (methyl) acrylate, Nonylphenoxy tetraethylene glycol (methyl) acrylate, methoxyl group diethylene glycol (methyl) third
Olefin(e) acid ester, ethoxydiglycol (methyl) acrylate, butoxyethyl group (methyl) acrylate, butoxytriglycol
(methyl) acrylate, 2- ethylhexyls polyethylene glycol (methyl) acrylate, nonyl phenyl polypropylene glycol (methyl) acrylic acid
Ester, methoxyl group dipropylene glycol (methyl) acrylate, (methyl) glycidyl acrylate, (methyl) acrylic acid 2- hydroxyl second
Ester, (methyl) acrylic acid 2- hydroxy propyl esters, glycerine (methyl) acrylate, polyethylene glycol (methyl) acrylate, polypropylene glycol
(methyl) acrylate, modification (methyl) butyl acrylate, epichlorohydrin are modified phenoxy group (methyl) acrylate, ethylene oxide changes
Property phthalic acid (methyl) acrylate, ethylene-oxide-modified succinic acid (methyl) acrylate, caprolactone modification (methyl)
Acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid N, N- dimethylamino ethyl ester, (methyl) acrylic acid N, N- diethylamino
Ethyl ester, morpholino (methyl) acrylate, ethylene-oxide-modified phosphoric acid (methyl) acrylate etc..Wherein, from making in non-freezing solution
In excellent curability viewpoint set out, preferably phenoxy group diethylene glycol (methyl) acrylate, phenoxy group tetraethylene glycol (first
Base) acrylate, Nonylphenoxy tetraethylene glycol (methyl) acrylate, methoxyl group diethylene glycol (methyl) acrylate, second
Oxygroup diethylene glycol (methyl) acrylate, butoxytriglycol (methyl) acrylate, 2- ethylhexyl polyethylene glycol
(methyl) acrylate, methoxyl group dipropylene glycol (methyl) acrylate, gathers nonyl phenyl polypropylene glycol (methyl) acrylate
Ethylene glycol (methyl) acrylate, polypropylene glycol (methyl) acrylate, ethylene-oxide-modified phthalic acid (methyl) propylene
Acid esters, ethylene-oxide-modified succinic acid (methyl) acrylate, ethylene-oxide-modified phosphoric acid (methyl) acrylate etc..
As two functional monomers, it can be mentioned, for example 1,3-BDO two (methyl) acrylate, 1,4-butanediol two
(methyl) acrylate, neopentyl glycol two (methyl) acrylate, 1,6-hexylene glycols two (methyl) acrylate, ethylene glycol two
(methyl) acrylate, triethylene glycol two (methyl) acrylate, polyethylene glycol two (methyl) acrylate, two (first of propylene glycol
Base) acrylate, tripropylene glycol two (methyl) acrylate, ethylene-oxide-modified neopentyl glycol two (methyl) acrylate, ring
Ethylene Oxide is modified neopentyl glycol two (methyl) acrylate, 3-hydroxypivalic acid ester neopentylglycol diacrylate, caprolactone modification
3-hydroxypivalic acid ester neopentylglycol diacrylate, neopentyl glycol are modified trimethylolpropane two (methyl) acrylate, tristearin
Two (methyl) acrylate of the modified pentaerythrite of acid, diacrylate dicyclopentenyl ester, ethylene-oxide-modified two (methyl) acrylic acid
Dicyclopentenyl ester, two (methyl) acryloyl group isocyanuric acid esters etc..Wherein, from keeping the curability in non-freezing solution excellent such
Viewpoint is set out, preferably 1,3-BDO two (methyl) acrylate, 1,4-butanediol two (methyl) acrylate, ethylene glycol two
(methyl) acrylate, triethylene glycol two (methyl) acrylate, polyethylene glycol two (methyl) acrylate, two (first of propylene glycol
Base) acrylate, tripropylene glycol two (methyl) acrylate, ethylene-oxide-modified neopentyl glycol two (methyl) acrylate, ring
Ethylene Oxide is modified neopentyl glycol two (methyl) acrylate, ethylene-oxide-modified two (methyl) acrylic acid dicyclopentenyl ester etc..
As trifunctional's monomer, it can be mentioned, for example trimethylolpropane tris (methyl) acrylate, three (first of pentaerythrite
Base) acrylate, ethylene-oxide-modified trimethylolpropane tris (methyl) acrylate, epoxy pronane modification trimethylolpropane
Three (methyl) acrylate, epichlorohydrin are modified trimethylolpropane tris (methyl) acrylate, three (first of epichlorohydrin modified glycerol
Base) acrylate, three (acryloyl-oxyethyl) isocyanuric acid esters etc., wherein from making the excellent curability in non-freezing solution
Viewpoint is set out, and ethylene-oxide-modified trimethylolpropane tris (methyl) acrylate, epoxy pronane modification trihydroxy methyl can be enumerated
Propane three (methyl) acrylate etc..
As multi-functional monomer, it can be mentioned, for example two (trihydroxy methyl) propane four (methyl) acrylate, pentaerythrites
Four (methyl) acrylate, dipentaerythritol monohydroxy five (methyl) acrylate, five acrylic acid of alkyl-modified dipentaerythritol
Ester, dipentaerythritol six (methyl) acrylate, caprolactone modification dipentaerythritol six (methyl) acrylate etc..These polymerizations
Property monomer can be used alone or be used in the form of two or more mixtures.
In turn, the purpose of the viscosity for the upper anaerobically curable bonding agent of adjustment or the characteristic for adjusting its solidfied material, can be with
Make to contain polyreactive oligomers in above-mentioned polymerizable monomer.As the polyreactive oligomers, it can be mentioned, for example polybutadiene bones
Carbamate (methyl) acrylate of frame, carbamate (methyl) acrylate, the poly- carbon of hydrogenated butadiene polymer skeleton
Carbamate (methyl) acrylate of acid esters skeleton, carbamate (methyl) acrylate, the polyester bone of polyether skeleton
Carbamate (methyl) acrylate of frame, carbamate (methyl) acrylate, the isoprene of castor oil skeleton
(methyl) acrylate, epoxy (methyl) acrylate, contains (methyl) acryloyl at hydrogenated isoprene system (methyl) acrylate
The acrylate copolymer of base, the polyisobutene etc. for containing (methyl) acryloyl group.As (A) ingredient, preferred polycarbonate backbone
The amino first of carbamate (methyl) acrylate, carbamate (methyl) acrylate of polyether skeleton, polyester backbone
Acid esters (methyl) acrylate, epoxy (methyl) acrylate, the further preferably carbamate (methyl) of polyether skeleton
Acrylate, epoxy (methyl) acrylate.These oligomer can be used alone or with the shape of two or more mixtures
Formula uses.
As the concrete example of epoxy (methyl) acrylate, can enumerate by bisphenol-type epoxy resin, phenol novolak type epoxy
The epoxy resins such as the terminal glycidyl group ether of the alkylene oxide addition product of resin, bisphenol-A or Bisphenol F and (methyl) acrylic acid
Compound (such as Ethoxylated bisphenol A dimethylacrylates) that reactant etc. obtains etc..Wherein, from making in non-freezing solution
Excellent curability viewpoint is set out, particularly preferably for by the terminal glycidyl group ether of bisphenol-A or the alkylene oxide addition product of Bisphenol F
Compound obtained from equal epoxy resins and the reactant of (methyl) acrylic acid etc..
As the epoxy resins such as terminal glycidyl group ether by bisphenol-A or the alkylene oxide addition product of Bisphenol F and (first
Base) acrylic acid the obtained commercially available product of compound such as reactant, can enumerate BPE-80N, BPE-100, BPE-200,
BPE-500, BPE-900, BPE-1300N (villages Xin Zhong chemical industry Co. Ltd. system), (Osaka organises VISCOAT#700
Learn industrial group system), FA-324A, FA-321M (Hitachi Chemical Co., Ltd.'s system), LIGHT ACRYLATE BP-4EAL,
BP-4PA (Kyoeisha Chemical Co., Ltd.'s system) etc., wherein it is preferable to use BPE-100 (chemical industry Co., Ltd. of the villages Xin Zhong
System).
< (B) ingredients >
As (B) ingredient radical polymerization initiator used in the present invention, it is free that organic peroxide, light can be enumerated
Base propellant etc., in the present invention, from the viewpoint of anaerobically curable, preferred organic peroxide.As organic peroxy
Object, it can be mentioned, for example：Cumene hydroperoxide, tert-butyl hydroperoxide, p-methane hydroperoxide, methyl-ethyl-ketone peroxide,
The hydroperoxide kinds such as cyclohexane peroxide, dicumyl peroxide, diisopropyl benzene hydrogen peroxide；And peroxidating ketone, two
Organic peroxides such as allyl peroxide, peroxyesters etc..These organic peroxides can be used alone or
Person is used in the form of two or more mixtures.Wherein, steady from the long-term preservation of reactivity and anaerobically curable bonding agent
, it is preferable to use hydroperoxide kind, more preferably uses cumene hydroperoxide from the perspective of qualitative.
It as above-mentioned optical free radical propellant, is not particularly limited, it can be mentioned, for example the polymerizations of acetophenone system optical free radical
Initiator, benzoin system optical free radical polymerization initiator, benzophenone series optical free radical polymerization initiator, thioxanthones system light are free
Base polymerization initiator, acylphosphine oxide system optical free radical polymerization initiator, titanocenes system optical free radical polymerization initiator etc..
The use level of (B) ingredient is preferably 0.1~5 mass parts, more preferably 0.5 relative to 100 mass parts of (A) ingredient
~1.5 mass parts.At this point, more than if it is 0.1 mass parts, then polymerisation fully occurs.It is below mass part if it is 5,
It then may insure the storage stability of anaerobically curable resin combination.
< (C) ingredients >
As the anaerobism polymerization accelerant of (C) ingredient as used in the present invention, amine compounds, azoles chemical combination can be enumerated
They, can be used singly or in combination by object, mercaptan compound, hydrazine compound and their derivative etc..They can be with
It is used alone or is used in the form of two or more mixtures.It is explained, anaerobism is used for usually together with (B) ingredient
Hardening resin composition.
By coordinating ingredient (C) ingredient, so as to reach good anaerobically curable.(C) additive amount of ingredient is excellent
Phase selection coordinates 100 mass parts of (A) ingredient with 0.1~10 mass parts, is more preferably coordinated with 1~3 mass parts.
As above-mentioned amine compounds, it can be mentioned, for example：1,2,3,4- tetrahydroquinolines, 1,2,3,4- tetrahydrochysene quinaldines etc. are miscellaneous
Ring secondary amine；The heterocyclic tertiary amines such as quinoline, methylquinoline, quinaldine, quinoxaline azophenlyene；N, N- dimethyl-aminoanisole, N,
Aromatic nitrile bases such as accelerine etc..
As above-mentioned azole compounds, it can be mentioned, for example thiazole, isothiazole, thiadiazoles, oxazole, isoxazole, oxadiazoles, two
Azoles, triazole etc..More specifically, saccharin, benzothiazole, 1,2,4- triazoles, benzotriazole, hydroxybenzotriazole, benzene can be enumerated
Bing oxazoles, 1,2,3- diazosulfides, 3- sulfhydryl benzotriazoles etc..
As above-mentioned mercaptan compound, the straight chain type thiols such as n-dodecyl mercaptan, ethanethio, butanethiol can be enumerated
Deng, but it's not limited to that.
As above-mentioned hydrazine compound, can enumerate 1- acetyl group -2- phenyl hydrazines, 1- acetyl group -2 (p-methylphenyl) hydrazine,
1- benzoyl -2- phenyl hydrazines, 1- (1 ', 1 ', 1 '-trifluoro) acetyl group -2- phenyl hydrazines, 1,5- diphenyl-phosphinylidyne
Hydrazine, 1- formoxyl -2- phenyl hydrazines, 1- acetyl group -2- (p-bromophenyl) hydrazine, 1- acetyl group -2- (p-nitrophenyl)
Hydrazine, 1- acetyl group -2- (2 '-phenylethyl hydrazine), ethyl carbazate, paranitrophenylhydrazine, to three sulfonyl hydrazines etc., still
It's not limited to that.
In (C) ingredient, from the viewpoint of keeping anaerobically curable excellent, preferred azole compounds.More specifically, preferably
Saccharin and/or benzothiazole, more preferable saccharin.
< (D) ingredients >
The nonionic surfactants of (D) ingredient used in the present invention pass through the other compositions group with the present invention
It closes, to making the solidfied material of anaerobically curable resin in non-freezing solution become smaller and spy that is more crisp, being easy micronized
Property.Usually as surfactant, it is roughly divided into anionic surfactant, cationic system surfactant, nonionic system
Four kinds of surfactant, amphoteric surfactant, but in the present invention, it was discovered that only nonionic surfactants have heterogeneous effect
It answers.As above-mentioned nonionic surfactants, it is non-that poly (oxyalkylene) fundamental mode nonionic surfactants, polyol type can be enumerated
Ionization series surfactant, sugar-type nonionic surfactants, wherein make the anaerobically curable tree in non-freezing solution from existing
Tendency that the solidfied material of fat becomes smaller and with it is more crisp, be easy characteristic as micronized from the perspective of, preferred poly (oxyalkylene)
Fundamental mode nonionic surfactants or polyol type, more preferable polyol type.These ingredients can be used alone, can also
It is applied in combination.
As above-mentioned poly (oxyalkylene) fundamental mode nonionic surfactants, it is sub- that polyoxyalkylene alkyl ether, polyoxy can be enumerated
Alkyl diol etc..As polyoxyalkylene alkyl ether, from making the aspect excellent in compatibility with (A) ingredient of the present invention,
HLB value is preferably 6~16 range, more preferably 7~15 range.It is explained, HLB refers to Hydrophile-
Lipophile balance (hydrophile-lipophile balance) are the hydrophilic radical and lipophilic group of the intramolecular for indicating surfactant
The index of the balance of group.HLB in the present invention is the value calculated using Griffin methods.In addition, as polyoxyalkylene alkyl ether
Commercially available product, it can be mentioned, for example Noigen XL-80, Noigen XL-160, Noigen TDS-30, Noigen TDS-
70, Noigen LF-100X, Noigen LF-202N, Noigen TDX-50, Noigen TDX-100D (the first industry systems
Medicine Co. Ltd. system) etc..As the commercially available product of polyether polyols, it can be mentioned, for example Emanon 1112, Emanon 3199V
(Kao Corp's system) etc..
As above-mentioned polyol type nonionic surfactants, fatty acid glyceride, sorbitan esters of fatty can be enumerated
Acid esters, polyoxyethylene sorbitan fatty acid ester etc., wherein from the solidfied material for making the anaerobically curable resin in non-freezing solution
From the perspective of for weaker power and becoming tiny immediately, preferably glycerine aliphatic ester.As commercially available product, Chirabasol can be enumerated
W-01, Chirabasol W-02, Chirabasol D-818M (Sun Chemical Co., Ltd.'s system) etc..
As above-mentioned sugar-type nonionic surfactants, sucrose fatty ester, alkyl polyglucoside etc. can be enumerated.
(D) additive amount of ingredient is preferably 0.1~50 parts by weight relative to above-mentioned 100 parts by weight of (A) ingredient, more preferably
1~40 parts by weight, particularly preferably 3.5~35 parts by weight.It is below mass part if it is 50, then it can maintain high anaerobic curing
Property.In addition, more than if it is 0.1 parts by weight, then obtain as more crisp, the easy micronized of the cured solidfied material in non-freezing solution
Effect of the present invention.
For the present invention, can be used in the range of not damaging the purpose of the present invention various elastomers, preserving stabilizer,
Antioxidant, light stabilizer, preserving stabilizer, heavy metal deactivator, silane coupling agent, tackifier, plasticizer, antifoaming agent, face
The additives such as material, antirust agent, levelling agent, dispersant, rheology modifier, fire retardant.
For the present invention, as a purpose with elasticity modulus, mobility for improveing solidfied material etc., it can add and not hinder to preserve
The packing material of the degree of stability.Specifically, organic matter powder, inanimate matter powder etc. can be enumerated.
It as the packing material of inanimate matter powder, is not particularly limited, but glass, aerosil, oxidation can be enumerated
Aluminium, mica, ceramics, silicone rubber powder, calcium carbonate, aluminium nitride, carbon dust, kaolin clay, dry clay mineral, dry diatom
Soil etc..The use level of inanimate matter powder is preferably 0.1~100 mass parts or so relative to 100 mass parts of (A) ingredient.
Coordinate for the purpose of the viscosity for adjusting anaerobically curable resin combination or the mechanical strength for improving solidfied material
Aerosil.It is preferable to use with dimethylsilane, trimethyl silane, alkyl silane, methacryloxypropyl silane, organic
Chlorosilane, dimethyl silicone polymer, hexamethyldisilazane etc. be surface-treated after aerosil etc..As gas phase
The commercially available product of silica, it can be mentioned, for example 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. (Japanese Aerosil Co. Ltd. systems).
As the packing material of organic matter powder, be not particularly limited, but it can be mentioned, for example polyethylene, polypropylene, nylon,
Cross-linked acrylic acid, crosslinked polystyrene, polyester, polyvinyl alcohol, polyvinyl butyral, makrolon.Organic matter powder is matched
Resultant is preferably 0.1~100 mass parts or so relative to 100 mass parts of (A) ingredient.
For the present invention, preserving stabilizer can be added.As preserving stabilizer, can also add：Benzoquinones, to benzene two
The free base absorbant such as phenol, hydroquinone monomethyl ether；Ethylenediamine tetra-acetic acid or ethylenediamine tetra-acetic acid -2- sodium salts, oxalic acid, second
Metallo-chelates agent such as acyl acetone, o-aminophenol etc..
For the present invention, antioxidant can be added.As antioxidant, it can be mentioned, for example：Beta-naphthoquinone, 2- methoxies
Base -1,4- naphthoquinones, methyl hydroquinone, hydroquinone, hydroquinone monomethyl ether, mono- tert-butyl hydroquinone, 2,5-
The quinones system chemical combination such as di-tert-butyl hydroquinone, 1,4-benzoquinone, 2,5- diphenyl -1,4-benzoquinone, 2,5- di-t-butyls -1,4-benzoquinone
Object；Phenthazine, 2,2- methylene-bis- (4- methyl-6-tert-butylphenols), catechol, tert-butyl catechol, 2- fourths
Base -4-hydroxyanisol, 2,6- di-t-butyls-paracresol, 2- tertiary butyls -6- (3- tertiary butyl -2- hydroxyls -
5- methylbenzyls) -4- aminomethyl phenyls acrylate, 2- (1- (2- hydroxyl -3,5- di-tert-pentyl-phenyls) ethyl) -
4,6- di-tert-pentyl-phenyls acrylate, 4,4 '-butylidenebis (6- tertiary butyl -3- methylphenols), 4,4 '-thiobis
Bis- (2- (3- (3- tertiary butyl-4-hydroxy -5- aminomethyl phenyls) propionyl of (6- tertiary butyl -3- methylphenols), 3,9-
Oxygroup) -1,1- dimethyl ethyls) -2,4,8,10- four oxaspiro (5,5) hendecane, the (3- (3,5- bis- of pentaerythrite four
Tert-butyl-hydroxy phenyl) propionic ester), the bis- (3- (3,5- di-tert-butyl-hydroxy phenyls) third of thiodiethylene
Acid esters), octadecyl -3- (3,5- di-tert-butyl-hydroxy phenyls) propionic ester, N, N '-hexane -1,6- diyls are double
(3- (3,5- di-tert-butyl-hydroxy phenyls) propionamide), bis- (1,1- the dimethyl ethyls) -4- hydroxy benzenes third of 3,5-
Sour C7-C9 pendant alkyl groups ester, 2,4- dimethyl -6- (1- methyl pentadecyl) phenol, diethyl ((3,5- it is bis- (1,
1- dimethyl ethyls) -4- hydroxy phenyls) methyl) phosphonate ester, 3,3 ', 3 ", 5,5 ', 5 "-six tertiary butyl-a, a ', a " -
Bis- ((bis- (1,1- the dimethyl ethyls) -4- hydroxyls of 3,5- of (mesitylene -2,4,6- tolyls) three paracresol, diethyl
Phenyl) methyl) phosphonic acids calcium, bis- (pungent butylthiomethyl) o-cresols of 4,6-, bis- (3- (the tertiary fourths of 5- of ethylenebis (oxygroup ethylidene)
Tolyl between base -4- hydroxyls) propionic ester), hexamethylene bis (3- (3,5- di-t-butyl -4- hydroxy phenyls) propionic acid
Ester, 1,3,5- tri- (3,5- di-tert-butyl-4-hydroxyl benzyls) -1,3,5- triazines -2,4,6 (1H, 3H, 5H)-triketone,
1,3,5- tri- ((4- tertiary butyl -3- hydroxyls -2,6- xylyl) methyl) -1,3,5-triazines -2,4,6 (1H, 3H,
Reaction product, the 2,6- di-t-butyl -4- (4,6- of 5H)-triketone, N- phenylanilines and 2,4,6- trimethylpentenes
Bis- (pungent sulfenyl) -1,3,5- triazine -2- bases amino) phenols such as phenol, picric acid, citric acid；Three (2,4- di-t-butyls
Phenyl) phosphite ester, three (2- ((2,4,8,10- tetra-tert dibenzo (d, f) (1,3,2) dioxaphosphepin cycloheptatriene
(dioxaphosphepine) -6- bases) oxygroup) ethyl) amine, bis- (2,4- di-tert-butyl-phenyls) pentaerythrite diphosphorous acids
Bis- (bis- (1,1- the dimethyl ethyls) -6- aminomethyl phenyls of the 2,4-) ethyl esters of ester, phosphorous acid, four (2,4- di-tert-butyl-phenyls)
(the bis- phenyl of 1,1-) -4,4 '-diyl biphosphinates, 6- (3- (3- tertiary butyl-4-hydroxy -5- aminomethyl phenyls)
Propoxyl group) phosphorus series compounds such as -2,4,8,10- tetra-tert dibenzo (d, f) (1,3,2) dioxaphosphepin cycloheptatriene；
3,3 '-dilauryl thiodipropionates, 3,3 '-thio-2 acid, two myristin, 3,3 '-distearylthiodi-propionates,
The chalcogenide compounds such as pentaerythrite four (3- lauryl thiopropionates), 2-mercaptobenzimidazole；The amine systems chemical combination such as phenthazine
Object；Lactone based compound；Vitamin E based compound etc..Wherein, preferred phenol system compound.
For the present invention, silane coupling agent can be added.It as silane coupling agent, is not particularly limited, but can enumerate
γ-r-chloropropyl trimethoxyl silane, octenyl trimethoxy silane, glycidoxy octyl trimethoxy silane, β-(3,
4- epoxycyclohexyls) ethyl trimethoxy silane, γ-glycidoxypropyltrime,hoxysilane, γ-ureido-propyl three
Ethoxysilane, to styryltrimethoxysilane etc..The content of adaptation imparting agent is relative to 100 mass of (A) ingredient
Part is preferably 0.05~30 mass parts, further preferably 0.2~10 mass parts.
The anaerobically curable resin combination of the present invention sharp can by a conventionally known method manufacture.Such as it can pass through
Following manner manufactures, that is, (A) ingredient~(D) ingredient for coordinating specified amount, using mixed medias such as mixing machines, preferably 10
It is mixed at a temperature of~100 DEG C preferably 0.1~5 hour.
The anaerobically curable resin combination of the present invention is suitable for：Screw, bolt etc. are bonded, fix；Gomphosis part
Fixation, bonding, sealing；The filling etc. of the stomata generated in cast part.Especially have the curability in non-freezing solution excellent
Different and solidfied material is more crisp, is easy characteristic as micronized, therefore extremely effective with sealant as the strange plug of Weir.According to using
The Weir very plug sealant of above-mentioned anaerobically curable resin combination, even if excellent if anaerobically curable in non-freezing solution,
Therefore uncured resin will not be made to enter the gap of the components such as valve or the blade of water pump and cure and cause unfavorable condition.In turn,
Since solidfied material is more crisp, it is easy micronized, therefore with the fortune that will not crush and prevent valve or blade under smaller stress
Dynamic effect.
Embodiment
Hereinafter, enumerating embodiment, the present invention will be described in more detail, but the present invention is not by these embodiments
It limits.
The test method(s) used in Examples and Comparative Examples is for example following shown.
The preparation > of < anaerobically curable resin combinations
Addition：As the present invention (A) ingredient triethylene glycol dimethacrylate (LIGHT ACRYLATE 3EG,
Kyoeisha Chemical Co., Ltd.'s system) 70 mass parts and the Ethoxylated bisphenol A dimethylacrylates (village BPE-100, Xin Zhong
Learn Industrial Co., Ltd's system) 30 mass parts；
Cumene hydroperoxide (NOF Corp's system) 1 mass parts as (B) ingredient；
1 mass parts of saccharin, 0.1 mass parts of benzothiazole as (C) ingredient；With
The comparison ingredient of (D) ingredient or (D) ingredient shown in the table 1 of specified amount,
At normal temperatures utilize mixing machine mix 60 minutes, prepare Examples 1 to 9, comparative example 1~6 anaerobically curable tree
Oil/fat composition.Numerical value is all indicated with mass parts.
< (D) ingredients >
d1：Polyoxy alkylidene branch last of the ten Heavenly stems ether (polyoxyalkylene alkyl ether, Noigen XL-80, first that HLB is 13.8
Industrial pharmaceutical Co. Ltd. system)
d2：Polyoxyethylene tridecyl ether (polyoxyalkylene alkyl ether, Noigen TDS-30, first that HLB is 8
Industrial pharmaceutical Co. Ltd. system)
d3：Polyoxyethylene tridecyl ether (polyoxyalkylene alkyl ether, Noigen TDS-70, first that HLB is 12
Industrial pharmaceutical Co. Ltd. system)
d4：Polyoxyalkylene alkyl ether (polyoxyalkylene alkyl ether, Noigen LF-100X, first that HLB is 14.5
Industrial pharmaceutical Co. Ltd. system)
d5：Polyethylene glycol mono stearate (Emanon 3199V, Kao Corp's system)
d6：Glycerine lipid aliphatic ester (Chirabasol W-01, Sun Chemical Co., Ltd.'s system)
d7：Glycerine lipid aliphatic ester (Chirabasol W-02, Sun Chemical Co., Ltd.'s system)
The comparison ingredient > of < (D) ingredient
d'1：Dodecyl sulphate Na (anionic surfactant, reagent)
d'2：Lauric acid Na (anionic surfactant, reagent)
d'3：Polyoxyethylene tridecyl ether sulfuric acid Na (anionic surfactant, Hitenol 330T, the first work
Industry Pharmaceutical Co., Ltd system)
d'4：Lauryl trimethyl ammonium chloride (cationic system surfactant, QUARTAMIN 24P, Kao Corp
System)
d'5：Stearyl trimethyl ammonium chloride (cationic system surfactant, QUARTAMIN 86W, Kao Corp
System)
The test method used in the embodiment of table 1, comparative example is for example following shown.
The confirmation > of curability of the < in non-freezing solution
The pure SUPER LLC of TOYOTA (are diluted to by 50% non-freezing solution that 40 mass parts are weighed in beaker with pure water
Solution after 50%), each 10 mass parts of anaerobically curable resin combination modulated are added thereto.While being stirred with air motor
Machine is mixed to be stirred with 300rpm, while be heated up to 100 DEG C, after five minutes, with visual confirmation anaerobically curable resin combination whether there is or not
Solidification.The case where solidification will be confirmed, is evaluated as "○", "×" will be evaluated as the case where failing to confirm solidification, by result
It is summarized in table 1.
The confirmation > for the solidfied material size that < is obtained in non-freezing solution
The size of solidfied material using microscope to being tested by the curability in non-freezing solution is confirmed.It is based on
Following benchmark are evaluated.The results are shown in Table 1.As a result smaller, it is the more preferred.If evaluation result be " in " " small ", making
In the case of for the Weir very use of plug sealant, the movement of the valve or blade of water pump will not be prevented, therefore it is preferred that.
Evaluation criteria
Greatly：20mm or more
In：5mm or more and less than 20mm
It is small：Less than 5mm
The brittleness of < solidfied materials, the confirmation > of micronized
Experimenter applies 60N with the sharp stick of hand-hold front end to the solidfied material tested by the curability in non-freezing solution
Load, based on following benchmark evaluations destructible of solidfied material.It is explained, in particle after disruption, confirms ruler
Very little maximum particle is as object.The results are shown in Table 1.If evaluation result is "○", as Weir very plug sealant
In the case of use, the movement of the valve or blade of water pump will not be prevented, therefore it is preferred that.
Evaluation criteria
○：The case where if applied force is destroyed, and particle size is less than 1mm
△：If applied force is destroyed, particle size is the situation of 1mm or more
×：The case where not being destroyed applied force
[table 1]
According to table 1, it is known that it is excellent and solid with the curability in non-freezing solution to belong to the embodiment of the present invention 1~9
Compound is more crisp, is easy the anaerobically curable resin combination of characteristic as micronized.Wherein, fatty acid glyceride has been used
The solidfied material that embodiment 6~9 obtains in non-freezing solution is small, be especially suitable for Weir very plug sealant.
In addition, comparative example 1 is the anaerobically curable resin combination without surfactant, but in non-freezing solution after solidification
Solidfied material size it is big, and solidfied material is hard, therefore as Weir very plug sealant, there are prevention water pumps
Valve or blade movement risk.Comparative example 2~4 is the anaerobically curable resin combination containing anionic surfactant
Object, if but the solidfied material applied force after curing in non-freezing solution, be destroyed, the size of particle is 1mm or more, with bravado
In the case of Er Qisai sealants, there is the risk of the movement of the valve or blade that prevent water pump.Comparative example 5,6 be containing sun from
The anaerobically curable resin combination of subsystem surfactant, the solidfied material after curing in non-freezing solution is hard, therefore with bravado
In the case of Er Qisai sealants, there is the risk of the movement of the valve or blade that prevent water pump.
Utilization possibility in industry
The anaerobically curable resin combination of the present invention is suitably applied：Screw, bolt etc. are bonded, fix；Fitting portion
Fixation, bonding, the sealing of part；The filling etc. of the stomata generated in cast member.Especially there is the curability in non-freezing solution
Excellent and solidfied material is more crisp, is easy characteristic as micronized, therefore extremely effective with sealant as the strange plug of Weir, therefore
It is useful in industry.
Claims (6)
1. a kind of anaerobically curable resin combination contains following (A)~(D) ingredients：
(A) ingredient：Compound with free-radical polymerised functional group,
(B) ingredient：Radical polymerization initiator,
(C) ingredient：Anaerobism polymerization accelerant,
(D) ingredient：Nonionic surfactants.
2. anaerobically curable resin combination according to claim 1, which is characterized in that (A) ingredient is with ring
(methyl) acrylate of oxygen alkyl structure.
3. anaerobically curable resin combination according to claim 1 or 2, which is characterized in that (D) ingredient be selected from
Poly (oxyalkylene) fundamental mode nonionic surfactants, polyol type nonionic surfactants and sugar-type nonionic system surface are lived
One or more of property agent.
4. anaerobically curable resin combination described in any one of claim 1 to 3, which is characterized in that (D) at
It is divided into poly (oxyalkylene) fundamental mode nonionic surfactants or polyol type nonionic surfactants.
5. anaerobically curable resin combination according to any one of claims 1 to 4, which is characterized in that (D) at
It is divided into fatty acid glyceride.
6. a kind of Weir very plug sealant, it uses anaerobically curable resin groups according to any one of claims 1 to 5
Close object.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016-046481 | 2016-03-10 | ||
| JP2016046481 | 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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| CN108779190A true CN108779190A (en) | 2018-11-09 |
| CN108779190B CN108779190B (en) | 2024-02-09 |
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| JP (1) | JP6892607B2 (en) |
| CN (1) | CN108779190B (en) |
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| CA3239466A1 (en) * | 2021-11-30 | 2023-06-08 | Toagosei Co., Ltd. | Anaerobic curing adhesive composition, bonded laminated body, and motor |
| CA3239459A1 (en) * | 2021-11-30 | 2023-06-08 | Yoshiaki Iwase | Anaerobic curing adhesive composition, bonded laminated body, motor, and primer composition for anaerobic curing |
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| 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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- 2017-02-24 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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| Publication number | Publication date |
|---|---|
| JP6892607B2 (en) | 2021-06-23 |
| CN108779190B (en) | 2024-02-09 |
| JPWO2017154616A1 (en) | 2019-01-17 |
| WO2017154616A1 (en) | 2017-09-14 |
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