CN115160962B - Anaerobic sealant and preparation method thereof - Google Patents
Anaerobic sealant and preparation method thereof Download PDFInfo
- Publication number
- CN115160962B CN115160962B CN202210928259.7A CN202210928259A CN115160962B CN 115160962 B CN115160962 B CN 115160962B CN 202210928259 A CN202210928259 A CN 202210928259A CN 115160962 B CN115160962 B CN 115160962B
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- CN
- China
- Prior art keywords
- monomer
- polymerization inhibitor
- anaerobic sealant
- accelerator
- methacrylic acid
- Prior art date
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- 239000000565 sealant Substances 0.000 title claims abstract description 101
- 238000002360 preparation method Methods 0.000 title abstract description 24
- 239000003112 inhibitor Substances 0.000 claims abstract description 102
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 100
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 150000001412 amines Chemical class 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 9
- 150000002923 oximes Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002989 phenols Chemical class 0.000 claims abstract description 4
- 150000004053 quinones Chemical class 0.000 claims abstract description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 claims description 156
- -1 t-butyl pivalate peroxide Chemical class 0.000 claims description 55
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 54
- 239000003822 epoxy resin Substances 0.000 claims description 46
- 229920000647 polyepoxide Polymers 0.000 claims description 46
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 24
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 24
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 23
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 22
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 22
- 229940081974 saccharin Drugs 0.000 claims description 21
- 235000019204 saccharin Nutrition 0.000 claims description 21
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 21
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 18
- 235000006408 oxalic acid Nutrition 0.000 claims description 18
- DZCCLNYLUGNUKQ-UHFFFAOYSA-N n-(4-nitrosophenyl)hydroxylamine Chemical group ONC1=CC=C(N=O)C=C1 DZCCLNYLUGNUKQ-UHFFFAOYSA-N 0.000 claims description 17
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000945 filler Substances 0.000 claims description 16
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 14
- 229940091173 hydantoin Drugs 0.000 claims description 14
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 13
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- NKZUYKIMCVNXPM-UHFFFAOYSA-N CC(C(=O)O)=C.N1C(=O)NC(=O)C1 Chemical compound CC(C(=O)O)=C.N1C(=O)NC(=O)C1 NKZUYKIMCVNXPM-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000004408 titanium dioxide Substances 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- ICXAPFWGVRTEKV-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-2-yl)phenyl]-1,3-benzoxazole Chemical compound C1=CC=C2OC(C3=CC=C(C=C3)C=3OC4=CC=CC=C4N=3)=NC2=C1 ICXAPFWGVRTEKV-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 4
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical group C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940067157 phenylhydrazine Drugs 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- XOKMRXSMOHCNIX-UHFFFAOYSA-N 6-methyl-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(C)=CC=C21 XOKMRXSMOHCNIX-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- 229920000927 poly(p-phenylene benzobisoxazole) Polymers 0.000 description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 15
- 239000004593 Epoxy Substances 0.000 description 13
- 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 13
- 229910010413 TiO 2 Inorganic materials 0.000 description 11
- 150000003512 tertiary amines Chemical class 0.000 description 11
- 239000002245 particle Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- POYODSZSSBWJPD-UHFFFAOYSA-N 2-methylprop-2-enoyloxy 2-methylprop-2-eneperoxoate Chemical compound CC(=C)C(=O)OOOC(=O)C(C)=C POYODSZSSBWJPD-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
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- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- BXIQXYOPGBXIEM-UHFFFAOYSA-N butyl 4,4-bis(tert-butylperoxy)pentanoate Chemical compound CCCCOC(=O)CCC(C)(OOC(C)(C)C)OOC(C)(C)C BXIQXYOPGBXIEM-UHFFFAOYSA-N 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PTWJGGCOPUFTFL-UHFFFAOYSA-N cyclohexane;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1CCCCC1 PTWJGGCOPUFTFL-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- SCOAVUHOIJMIBW-UHFFFAOYSA-N phenanthrene-1,2-dione Chemical class C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1 SCOAVUHOIJMIBW-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- CDIHFAGKBHEFED-UHFFFAOYSA-N propan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound C(CCCCCC(C)(C)C)(=O)OOC(C)C CDIHFAGKBHEFED-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 229940120731 pyruvaldehyde Drugs 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- VXHFNALHLRWIIU-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)C VXHFNALHLRWIIU-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09J151/085—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds on to polysiloxanes
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
Abstract
The application discloses an anaerobic sealant and a preparation method thereof. The anaerobic sealant comprises a monomer-polymerization inhibitor mixture; an initiator selected from one or more of organic peroxides; a first accelerator and a second accelerator, which are respectively selected from one or more of a first amine, hydrazine and derivatives thereof, mercaptan or a first organic dibasic acid; a co-accelerator selected from one or more of a sugar salt or a second organic dibasic acid; a first polymerization inhibitor and a second polymerization inhibitor, which are respectively selected from one or more of phenols, quinones, oximes, azo compounds or second amines; wherein the mass ratio of the monomer-polymerization inhibitor mixture, the initiator, the first accelerator, the second accelerator, the auxiliary accelerator, the first polymerization inhibitor and the second polymerization inhibitor is 100:1.6-2.0:0.33-0.35:0.8-1.0:0.04-0.05:0.10-0.11:0.014-0.015.
Description
Technical Field
The application relates to the chemical field, in particular to an anaerobic sealant and a preparation method thereof.
Background
Since the rapid development of industrialization, the leakage of various industrial media (including acid, alkali, water, oil, gas, heat, and other various chemical agents) has long led to the damage of ecological environment, human life safety, and property loss. Generally, such industrial media are stored and transported using containers and/or piping. To prevent leakage from these containers and/or pipes, sealants are widely used. Anaerobic sealants are adhesives that do not cure when in contact with air or oxygen and remain in a liquid form for extended periods of time, yet cure rapidly when isolated from air or oxygen. The anaerobic sealant for sealing needs to be tightly sealed, and needs to be high-temperature resistant and high-leakage-pressure resistant in order to meet industrial scenes.
Disclosure of Invention
In order to solve the problems, the application provides an anaerobic sealant and a preparation method thereof. The anaerobic sealant is high-temperature resistant, high-permeability resistant and pressure-resistant.
In one aspect, the present application provides an anaerobic sealant comprising a monomer-inhibitor mixture; an initiator selected from one or more of organic peroxides; a first accelerator and a second accelerator, which are respectively selected from one or more of a first amine, hydrazine and derivatives thereof, mercaptan or a first organic dibasic acid; a co-accelerator selected from one or more of a sugar salt or a second organic dibasic acid; and a first polymerization inhibitor and a second polymerization inhibitor, each of which is one or more selected from phenol, quinone, oxime, azo compound, and second amine; wherein the mass ratio of the monomer-polymerization inhibitor mixture, the initiator, the first accelerator, the second accelerator, the auxiliary accelerator, the first polymerization inhibitor and the second polymerization inhibitor is 100:1.6-2.0:0.33-0.35:0.8-1.0:0.04-0.05:0.10-0.11:0.014-0.015.
In some embodiments, the monomers in the monomer-polymerization inhibitor mixture include methacrylic acid monomers including one or more of methacrylic acid, bisphenol a methacrylate epoxy resin monomers, polyether methacrylate epoxy resin monomers, tetrahydrofurfuryl methacrylate alcohol monomers, novolac methacrylate epoxy resin monomers, polybutadiene methacrylate epoxy resin monomers, silicone methacrylate modified epoxy resin monomers, hydantoin methacrylate epoxy resin monomers, and cyclohexane-1, 2-diglycidyl ester methacrylate monomers.
In some embodiments, the methacrylic acid monomer is a mixture of a silicone-modified epoxy monomer, a hydantoin methacrylate epoxy monomer, and a methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer, the silicone-modified epoxy monomer, the hydantoin methacrylate epoxy monomer, and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer being present in a mass ratio of 20-100%:0-40%:0-40%.
In some embodiments, the organic peroxide comprises one or more of di-t-butyl peroxide, benzoyl peroxide, cumene hydroperoxide, methyl ethyl ketone peroxide, t-butyl peroxybenzoate, t-butyl pivalate peroxide, t-butyl acetate peroxide, t-butyl benzoate peroxide, and cumene peroxide.
In some embodiments, the anaerobic sealant according to claim 4, wherein the organic peroxide is cumene hydroperoxide.
In some embodiments, the first amine comprises one or more of triethylamine, N-dimethylaniline, N-diethyl-p-toluidine, α -aminopyridine, 1,2,3, 4-tetrahydroquinoline, 1, 2-propanediamine, triethanolamine, dimethylamide.
In some embodiments, the first amine is triethylamine or N, N-dimethylaniline, the hydrazine and derivatives thereof are phenylhydrazine, the thiol is dodecyl thiol, and the first organic diacid is oxalic acid.
In some embodiments, the saccharinate comprises one or more of a SQ salt, a STQ salt, an SMQ salt.
In some embodiments, the saccharinate is an SQ salt and the second organic diacid is maleic acid.
In some embodiments, the phenol is hydroquinone or N-nitrophenol, the quinone is p-benzoquinone, the oxime is p-benzoquinone dioxime, and the second amine is N-nitrosodiphenylamine or sulfurized diphenylamine.
In some embodiments, the anaerobic sealant further comprises a filler comprising one or more of titanium dioxide, polytetrafluoroethylene, or poly-p-phenylene benzobisoxazole.
In some embodiments, the anaerobic sealant further comprises a solvent that is methacrylic acid or acrylic acid.
In yet another aspect, the present application provides a method for preparing the anaerobic sealant described above, the method comprising: mixing one or more monomer-polymerization inhibitor mixture; adding a first accelerator, a second accelerator, a first polymerization inhibitor and a second polymerization inhibitor, and stirring for a first period of time until the mixture is uniformly mixed; adding filler and stirring for a second time period until the filler and the second time period are uniformly mixed; and adding a second accelerator, an initiator and a solvent, and uniformly stirring until no precipitate exists to obtain the anaerobic sealant.
Detailed Description
As used in this application and in the claims, the terms "a," "an," "the," and/or "the" are not specific to the singular, but may include the plural, unless the context clearly dictates otherwise. In general, the terms "comprises" and "comprising" merely indicate that the steps and elements are explicitly identified, and they do not constitute an exclusive list, as other steps or elements may be included in a method or apparatus. Numerical ranges used in this application are for brevity and conciseness to describe each and every value within the range.
Some embodiments of the present application disclose an anaerobic sealant comprising a monomer-inhibitor mixture, an initiator, an accelerator, a co-accelerator, and an inhibitor.
The monomer may be a component of an anaerobic sealant for achieving adhesive properties (e.g., anaerobic cure), which may be polymeric. After the anaerobic sealant is cured, the monomers may form a polymer of a bodily form network. For example, the monomer may be a polymerizable or oligomer containing an unsaturated bond. In some embodiments of the present application, exemplary monomers may include methacrylic acid monomers including, but not limited to, methacrylic acid, dimethacrylate, polymethacrylic acid, bismethacrylic acid polyethylene glycol ester monomer, bisphenol a type epoxy resin monomer, tetrahydrofurfuryl methacrylate monomer, aliphatic epoxy methacrylate monomer, polyether methacrylate monomer, phenolic methacrylate epoxy monomer, hydantoin methacrylate epoxy monomer, silicone methacrylate epoxy monomer, organotitanium methacrylate epoxy monomer, methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer, methacrylic acid-trimellitic anhydride-triethylene glycol monomer, polyethylene glycol methacrylate monomer, polyurethane type methacrylate monomer, hydroxyethyl methacrylate monomer, hydroxypropyl methacrylate monomer, trimethylolpropane methacrylate monomer, polyol methacrylate monomer, polyethylene glycol dimethacrylate monomer, diethylene glycol dimethacrylate monomer, triethylene glycol dimethacrylate monomer, tetraethylene glycol dimethacrylate monomer, or any combination of monomers. Alternatively or preferably, the monomer may include one or more of methacrylic acid, bisphenol a methacrylate epoxy resin monomer, polyether methacrylate epoxy resin monomer, tetrahydrofurfuryl methacrylate alcohol monomer, novolac methacrylate epoxy resin monomer, polybutadiene methacrylate epoxy resin monomer, silicone methacrylate modified epoxy resin monomer, hydantoin methacrylate epoxy resin monomer, and methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer. Alternatively or preferably, the monomer may be a mixture of silicone-modified epoxy methacrylate monomers, hydantoin methacrylate epoxy monomers, and methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomers
Polymerization inhibitors, which may also be referred to as stabilizers, may be used to prevent polymerization of monomers during non-use (e.g., purification, storage, and/or transportation) overcharging, thereby affecting the performance of the anaerobic sealant. It is known that although oxygen can act as a polymerization inhibitor to some extent, it does not ensure that the anaerobic sealant has good storage stability. Therefore, the polymerization inhibitor can be added to further prevent the polymerization of the monomer, thereby achieving the purpose of long-term storage. In some embodiments of the present application, the polymerization inhibitor may be selected from one or more of phenols, quinones, oximes, azo compounds, or amines (which may be referred to as second amines in some embodiments of the present application). Exemplary phenols include phenol, halophenol, nitrophenol, hydrocarbylphenol, benzenediol, halophenol, hydrocarbylbenzenediol, benzenetriol, naphthol, naphthalenediol, and the like. Alternatively or preferably, the phenol may be hydroquinone, N-nitrophenol or 2,4, 6-trinitrophenol. Exemplary quinones may include benzoquinones (e.g., o-and p-benzoquinones), as well as naphthoquinones, anthraquinones, phenanthrenequinones, and the like. Alternatively or preferably, the quinone may be benzoquinone. Exemplary oximes include dimethyl ketoxime, methyl ethyl ketoxime, cyclohexanone oxime, benzophenone oxime, aldoxime, salicylaldoxime, bisphenylacetaldehyde oxime, butyraldehyde oxime, pyruvaldehyde dioxime, 1, 2-cyclohexanedione dioxime, p-benzoquinone dioxime, and the like. Alternatively or preferably, the oxime may be p-benzoquinone dioxime. Exemplary azo compounds include azobisisobutyronitrile, 4-methoxyazobenzene, p-nitrophenylaminoazobenzene, 2' -dihydroxyazobenzene, p-diaminoazobenzene, azo-tertiary butane, and the like. Exemplary second amines may include one or more of aliphatic amines, aromatic amines, or halogenated, hydrocarbon bands, or thio compounds thereof. Alternatively or preferably, the second amine may be N-nitrosodiphenylamine or sulfurized diphenylamine (also known as phenothiazine).
In some embodiments of the present application, the monomer-polymerization inhibitor mixture may be obtained by homogeneously mixing the monomer with the polymerization inhibitor. In some embodiments, the polymerization inhibitor may be added to the reaction system during the synthesis of the monomer, and remain after reaction and post-treatment without participating in the synthesis of the monomer. Finally, the monomer-polymerization inhibitor mixture can be obtained after the synthesis of the monomer is completed. The polymerization inhibitor is added in a very small amount, and its mass can be omitted as compared with the monomer. For further description of the monomer-inhibitor, reference may be made to the examples section of the present application.
In some embodiments of the present application, the polymerization inhibitor may include a portion mixed with the monomer, and may further include a first polymerization inhibitor and a second polymerization inhibitor. The first polymerization inhibitor may be 2,4, 6-trinitrophenol and the second polymerization inhibitor may be p-benzoquinone dioxime.
The initiator may be a component for initiating the polymerization of the monomer. After being isolated from air, the initiator may generate free radicals, thereby causing polymerization of the monomers. In the storage process, free radicals generated by the initiator are continuously consumed by the action of oxygen and a polymerization inhibitor (stabilizer), so that the anaerobic sealant is placed to fail after polymerization. In some embodiments of the present application, the initiator may be selected from organic peroxides. Exemplary organic peroxides may include alkyl hydroperoxides (e.g., t-butyl hydroperoxide, terpene hydroperoxide, dicumyl peroxide, t-butyl cumene peroxide, cumene hydroperoxide, t-amyl hydroperoxide, bis (t-butyl isopropyl peroxide) benzene, dicumyl peroxide, etc.), dialkyl peroxides (e.g., 2, 5-dimethyl-2, 5-bis (t-butyl peroxy) hexyne-3, 2, 5-dimethyl-2, 5-di-t-butyl ethane peroxide, di-t-amyl peroxide, di-t-butyl peroxide, etc.), acyl peroxides (e.g., dilauroyl peroxide, 3, 5-trimethylhexanoyl peroxide, dibenzoyl peroxide, etc.), peroxyketals (e.g., methyl ethyl ketone peroxide, 2-bis (t-butylperoxy) butane, 1-bis (t-butyl) peroxycyclohexane, 1-di-t-butylperoxy-3, 5-trimethylcyclohexane, 3,6, 9-triethyl-3, 6, 9-trimethyl-1, 4, 7-triperoxonane, and the like), peroxyesters (e.g., t-butyl peroxybenzoate, t-amyl peroxybenzoate, t-butyl pivalate, t-butyl peroxycarbonate-2-ethylhexyl, t-butyl peroxybenzoate, 2-ethyl-hexanoate, twenty-four peroxydicarbonate, isopropyl peroxyneodecanoate, n-butyl 4, 4-di (t-butyl peroxy) valerate, dicetyl peroxydicarbonate, and the like, bis (2-ethylhexyl) peroxydicarbonate, bis (4-tert-butylcyclohexyl) peroxydicarbonate, t-butyl peroxyacetate, t-butyl acetate, t-butyl benzoate, t-butyl peroxy-3, 5-trimethylhexanoate, t-butyl peroxyisobutyrate, t-butyl peroxy-2-ethylhexanoate, t-amyl peroxy-2-ethylhexanoate, t-butyl peroxypivalate, t-amyl peroxypivalate, cumyl peroxyneodecanoate, t-butyl peroxyneodecanoate, and the like), peroxydicarbonates (e.g., dicetyl peroxydicarbonate, bitetradecylperoxide, bis (4-tert-butylcyclohexyl) peroxydicarbonate, bis- (2-ethylhexyl) peroxydicarbonate, and the like), and the like. Alternatively or preferably, the initiator may comprise one or more of di-t-butyl peroxide, benzoyl peroxide, cumene hydroperoxide, methyl ethyl ketone peroxide, t-butyl peroxybenzoate, t-butyl pivalate peroxide, t-butyl acetate peroxide, t-butyl benzoate peroxide, and cumene peroxide. Alternatively or preferably, the initiator may be cumene hydroperoxide.
Accelerators may be components for accelerating the curing reaction. Upon being air-insulated, the accelerator may promote rapid polymerization of the monomer being initiated (e.g., the monomer that begins to polymerize). The initiator does not affect the storage period and the bonding strength of the anaerobic sealant while realizing the initiation function. In some embodiments of the present application, the anaerobic sealant includes a first accelerator and a second accelerator. The first and second accelerators may each be selected from one or more of amines (which may be referred to herein in some embodiments as first amines), hydrazines and derivatives thereof, thiols, or organic diacids (which may be referred to herein in some embodiments as first organic diacids). Exemplary first amines may include one or more of aliphatic amines, aromatic amines, or halogenated, hydrocarbon bands, or thio compounds thereof. Alternatively or preferably, the first amine may be one or more of triethylamine, N-dimethylaniline, N-diethyl-p-toluidine, aminopyridine, 1,2,3, 4-tetrahydroquinoline, 1, 2-propanediamine, triethanolamine, dimethylamide. Alternatively or preferably, the first amine may be triethylamine or N, N-dimethylaniline. Exemplary hydrazines and their derivatives include hydrazines, phenylhydrazines, substituted phenylhydrazines, hydrazides, substituted hydrazides, and the like. Alternatively or preferably, the hydrazine and its derivatives may be phenylhydrazine. Exemplary mercaptans may include alkyl mercaptans (e.g., methyl mercaptan, ethyl mercaptan, dodecyl mercaptan, etc.), aromatic mercaptans (e.g., benzyl mercaptan, p-hydroxy thiophenol, p-nitrophenthiophenol, etc.). Alternatively or preferably, the thiol may be dodecyl thiol. Exemplary first organic diacids may include aliphatic diacids (e.g., alkane diacids such as oxalic acid, malonic acid, succinic acid, etc., alkene diacids such as butene diacid, hexadiene diacid, etc.), aromatic diacids (e.g., phenyl diacids such as phthalic acid, benzene diacetic acid, benzene dipropionic acid, etc.). Alternatively or preferably, the first organic diacid may be oxalic acid. In some embodiments of the present application, the first promoter may be oxalic acid and the second promoter may be N, N-dimethylaniline.
The auxiliary accelerator may be a component for enhancing the effect of the accelerator, which has no remarkable accelerating effect when used alone, and which can remarkably enhance the effect of the accelerator when used together with the accelerator. In some embodiments of the present application, the co-accelerator may be selected from a sugar refinery salt or a second organic diacid. The saccharin salt may be a salt formed by reacting saccharin (chemical name of phthalimide) with other substances. Illustratively, the saccharin salts may include SQ salts (which salt saccharin with an amine such as a tertiary amine), STQ salts (which salt saccharin with 1,2,3, 4-tetrahydroquinoline), SMQ salts (which salt saccharin with 6-methyl-1, 2,3, 4-tetrahydroquinoline), SQA salts (which salt saccharin with 1,2,3, 4-tetrahydroquinoline), and the like. Alternatively or preferably, the saccharinate salt may be an SQ salt. The second organic diacid may also include aliphatic diacids (e.g., alkane diacids such as oxalic acid, malonic acid, succinic acid, etc., alkene diacids such as butene diacid, hexadiene diacid, etc.), aromatic diacids (e.g., phenyl diacids such as phthalic acid, benzene diacetic acid, benzene dipropionic acid, etc.), in comparison to the first organic diacid. Alternatively or preferably, the second organic diacid may be maleic acid. In some embodiments of the present application, the anaerobic sealant may further comprise a filler. The filler may include polymers, fibers, metals and their oxides, silicates, and the like. Alternatively or preferably, the filler may comprise one or more of titanium dioxide, polytetrafluoroethylene or poly-p-phenylene benzobisoxazole. Alternatively or preferably, the filler is a mixture of titanium dioxide, polytetrafluoroethylene and poly-p-phenylene benzobisoxazole. Wherein the mesh number of the titanium dioxide can be 200 mesh, 300 mesh, 400 mesh, 500 mesh, etc. Alternatively or preferably, the mesh number of the titanium dioxide may be 400 mesh. The average particle size of the polytetrafluoroethylene may be 10 to 50 μm. Alternatively or preferably, the polytetrafluoroethylene may have an average particle size of 15-40 μm. Alternatively or preferably, the polytetrafluoroethylene may have an average particle size of 20-30 μm. Alternatively or preferably, the polytetrafluoroethylene may have an average particle size of 20-25 μm. The average particle size of the poly (p-phenylene benzobisoxazole) may be 10 to 50 μm. Alternatively or preferably, the average particle size of the poly (p-phenylene benzobisoxazole) may be 15 to 40 μm. Alternatively or preferably, the average particle size of the poly (p-phenylene benzobisoxazole) may be 20 to 30 μm. Alternatively or preferably, the average particle size of the poly (p-phenylene benzobisoxazole) may be 20 to 25 μm.
In some embodiments of the present application, the anaerobic sealant may further comprise a solvent. The solvent may include acrylic acid or methacrylic acid. Alternatively or preferably, the solvent may be acrylic acid.
In some embodiments of the present application, the mass ratio (in parts by weight) of the monomer-polymerization inhibitor mixture, the initiator, the first accelerator, the second accelerator, the co-accelerator, the first polymerization inhibitor, and the second polymerization inhibitor is 100:1.6-2.0:0.33-0.35:0.8-1.0:0.04-0.05:0.10-0.11:0.014-0.015.
In some embodiments, the monomer-polymerization inhibitor mixture has a mass ratio of the silicone-modified epoxy methacrylate monomer, the hydantoin methacrylate epoxy monomer, and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer of 20-100:0-40:0-40. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 20:40:40. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 25:35:40. Alternatively or preferably, the mass ratio of the silicone-modified epoxy methacrylate monomer, the hydantoin methacrylate epoxy monomer, and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 33.33:33.33:33.33. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 40:30:30. Alternatively or preferably, the mass ratio of the methacrylic silicone modified epoxy resin monomer, the methacrylic hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 42.5:32.5:25. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 45:32.5:22.5. Alternatively or preferably, the mass ratio of the methacrylic acid silicone modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 50:25:25. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 50:30:20. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 50:20:30. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 60:20:20. Alternatively or preferably, the mass ratio of the methacrylic acid organosilicon modified epoxy resin monomer, the methacrylic acid hydantoin epoxy resin monomer and the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 100:0:0, that is, the monomer is one of the methacrylic acid organosilicon modified epoxy resin monomers.
Alternatively or preferably, the initiator may be 1.6, 1.8, 2.0, etc. parts by mass in the anaerobic sealant. The mass ratio of the first accelerator in the anaerobic sealant can be 0.33, 0.34, 0.35 and the like. The mass portion of the second accelerator in the anaerobic sealant can be 0.8, 0.9 and 1.0. The mass portion of the auxiliary accelerator in the anaerobic sealant can be 0.04 or 0.05. The first polymerization inhibitor can be 0.10 or 0.11 part by weight in the anaerobic sealant. The second polymerization inhibitor may be 0.014 or 0.015 parts by mass in the anaerobic sealant.
In some embodiments of the present application, the anaerobic sealant may be comprised of the monomer-inhibitor mixture, the initiator, the first accelerator, the second accelerator, the co-accelerator, the first inhibitor, the second inhibitor, the filler, and the solvent. The monomer-polymerization inhibitor mixture, the initiator, the first accelerator, the second accelerator, the co-accelerator, the first polymerization inhibitor, and the second polymerization inhibitor may include as described above. The filler may be composed of titanium dioxide, polytetrafluoroethylene, and poly-p-phenylene benzobisoxazole. The mass portion of the titanium dioxide in the anaerobic sealant can be 10-20. E.g., 10, 15, 20, etc. The mass portion of the polytetrafluoroethylene in the anaerobic sealant can be 15-20. For example 15 or 20. The mass portion of the poly-p-phenylene benzobisoxazole in the anaerobic sealant can be 18-20. E.g., 18, 19, 20, etc. The solvent may be acrylic acid. The mass fraction of acrylic acid in the anaerobic sealant may be 10.
Some embodiments of the application disclose a preparation method of the anaerobic sealant. The preparation method comprises the following steps. In the first step, one or more monomer-polymerization inhibitor mixtures are homogeneously mixed. The monomer-polymerization inhibitor mixture may be obtained during the preparation of the monomer. Wherein, the polymerization inhibitor can be added into the reaction system in the preparation process of the monomer, but does not participate in the reaction. After working up, a monomer-polymer mixture can be obtained. The desired monomer-polymerization inhibitor mixture may be added to a reaction vessel, such as a reaction kettle or beaker, flask, etc., and mixed with stirring until uniformly mixed. And secondly, adding a first accelerator, a second accelerator, a first polymerization inhibitor and a second polymerization inhibitor, and stirring for a first period of time until the mixture is uniformly mixed. The first time period may be a predetermined time period. For example, 10min, 20min, 30min, 40min, 50min, 60min, etc. The first time period can also be adjusted according to actual conditions. For example, it is appropriately lengthened or shortened according to the mixing condition. And thirdly, adding the filler and stirring for a second time period until the filler and the filler are uniformly mixed. The second time period may also be a preset time period, for example, 1h, 2h, 3h, etc., as well as the same or similar. And fourthly, adding a second accelerator, an initiator and a solvent, and uniformly stirring until no precipitate exists to obtain the anaerobic sealant. Wherein reference is made to the preceding description for the components and the amounts of the components.
Examples
The present application is further illustrated by the following examples. The present application is not limited by these examples.
Example 1 preparation of a monomer-Polymer mixture of methacrylic acid-cyclohexane-1, 2-diglycidyl ester
The reactants were obtained based on the following recipe:
100 g of cyclohexane-1, 2-diglycidyl ester was weighed into a four-necked flask. Heating, and adding 0.0665 g of hydroquinone when the temperature in the bottle reaches 60 ℃. 53.90 g of methacrylic acid are weighed and added at an internal temperature of 60 ℃. When the internal temperature reached 70 ℃, 1.7mL of triethylamine was added and mixed. And (3) regulating the temperature to 80-85 ℃ and reacting for 3h. Heating to 95-100 deg.c and reaction for 5 hr. After the reaction is finished, cooling to normal temperature, and putting into a polyethylene barrel. The reaction mechanism is as follows:
EXAMPLE 2 preparation of a silicone-modified epoxy monomer-Polymer mixture
The reactants were obtained based on the following recipe:
100 g of organic silicon epoxy resin is added into a four-mouth flask, heating is carried out to melt the organic silicon epoxy resin, 0.065 g of polymerization inhibitor hydroquinone is added into the four-mouth flask when the internal temperature reaches 60 ℃, 48 g of methacrylic acid is weighed, and the mixture is added when the internal temperature reaches 60 ℃. Adding 2mL of triethylamine when the internal temperature is gradually increased to 70 ℃, uniformly mixing, adjusting the temperature to 85-90 ℃ for reaction for 3h, continuously increasing the temperature to 90-95 ℃ for reaction for 4h until the reaction is finished, and pouring the mixture into a polyethylene barrel when the mixture is hot. The reaction mechanism is as follows:
examples 3-4) preparation of hydantoin methacrylate epoxy monomer-blocker mixtures
The reactants were obtained based on the following recipe:
100 g of hydantoin epoxy resin is placed into a four-necked flask, heated, and when the internal temperature reaches 60 ℃, 0.063 g of hydroquinone serving as a polymerization inhibitor is added into the four-necked flask, 46 g of methacrylic acid is weighed and added at the internal temperature of 60 ℃. And gradually heating to 70 ℃ and adding 1.6mL of triethylamine, uniformly mixing, regulating the temperature to 85-90 ℃ for reaction for 3h, continuously heating to 90-95 ℃ for heat preservation reaction for 4h until the reaction is finished, and pouring the mixture into a polyethylene barrel for standby when the reaction is hot to prepare the methacrylic acid-hydantoin epoxy resin monomer. The reaction mechanism is as follows:
example 4 preparation of anaerobic sealant
Anaerobic sealant S1: 20 parts of a monomer A-polymerization inhibitor mixture (a methacrylic acid organic silicon epoxy resin monomer-polymerization inhibitor mixture) is added into a flask under stirring, 40 parts of a monomer B-polymerization inhibitor mixture (a methacrylic acid hydantoin epoxy resin monomer-polymerization inhibitor mixture) is added, 40 parts of a monomer C-polymerization inhibitor mixture (a methacrylic acid cyclohexane 1, 2-triglyceryl ester monomer-polymerization inhibitor mixture) is added, the mixture is blended and stirred for 30min, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salt (SQ salt) are added, and the mixture is stirred uniformly for 30min. Adding 400 mesh TiO as filler 2 20 parts of polytetrafluoroethylene (20-25 mu m) 20 parts, 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m) and uniformly stirring for 1hAnd finally adding 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid, and stirring uniformly without precipitate.
Anaerobic sealant S2: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 25 parts of monomer A-polymerization inhibitor mixture, 35 parts of monomer B-polymerization inhibitor mixture, 40 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S3: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 33.3 parts of monomer A-polymerization inhibitor mixture, 33.3 parts of monomer B-polymerization inhibitor mixture, 33.3 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S4: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 40 parts of monomer A-polymerization inhibitor mixture, 30 parts of monomer B-polymerization inhibitor mixture, 30 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S5: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 42.5 parts of monomer A-polymerization inhibitor mixture, 32.5 parts of monomer B-polymerization inhibitor mixture, 25 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid and 0.4, 6-trinitrophenol11 parts, p-benzoquinone dioxime 0.15 parts, saccharin (insoluble) and tertiary amine salt (SQ salt) 0.05 parts, 400 mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S6: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 45 parts of monomer A-polymerization inhibitor mixture, 32.5 parts of monomer B-polymerization inhibitor mixture, 22.5 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S7: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 50 parts of monomer A-polymerization inhibitor mixture, 25 parts of monomer B-polymerization inhibitor mixture, 25 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S8: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 50 parts of monomer A-polymerization inhibitor mixture, 30 parts of monomer B-polymerization inhibitor mixture, 20 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S9: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass:50 parts of monomer A-polymerization inhibitor mixture, 20 parts of monomer B-polymerization inhibitor mixture, 30 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S10: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 50 parts of monomer A-polymerization inhibitor mixture, 25 parts of monomer B-polymerization inhibitor mixture, 25 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S11: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 60 parts of monomer A-polymerization inhibitor mixture, 20 parts of monomer B-polymerization inhibitor mixture, 20 parts of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Anaerobic sealant S12: the preparation process is the same as that of the anaerobic sealant S1, wherein the anaerobic sealant S1 comprises the following components in parts by mass: 100 parts of monomer A-polymerization inhibitor mixture, 0 part of monomer B-polymerization inhibitor mixture, 0 part of monomer C-polymerization inhibitor mixture, 0.35 part of oxalic acid, 0.11 part of 2,4, 6-trinitrophenol, 0.15 part of p-benzoquinone dioxime, 0.05 part of saccharin (insoluble) and tertiary amine salification (SQ salt) and 400-mesh TiO 2 20 parts of polytetrafluoroethylene (20-25 mu m), 20 parts of poly (p-phenylene benzobisoxazole) (20-25 mu m), 1 part of dimethylaniline, 2 parts of cumene hydroperoxide and 10 parts of acrylic acid.
Example 5 anaerobic sealant Performance test
1> tensile shear Strength: anaerobic sealant tensile shear strength test is carried out according to GB/T7124-2008;
2> viscosity test: anaerobic sealant viscosity test according to GB/T2794-2013
3> Heat resistance test: anaerobic sealant was prepared into a sealant rod (diameter 25mm, length 100 mm), heated at different temperatures for 10 hours, and the shrinkage of the sealant rod was measured. Anaerobic sealants can be determined to withstand a certain temperature when the sealant rod shrinkage is 0-0.1% at that temperature.
4> flame retardancy test: the anaerobic sealants were tested for flame retardancy using the burn test method for ANSI/UL94-1979 plastics.
The test results are shown in Table 1.
TABLE 1 anaerobic sealant Performance test results
As shown in Table 1, each test result shows that the average tensile shear strength of the anaerobic sealants S1-S12 can reach 20MPa, the heat resistance is above 200 ℃, and especially the heat resistance of the anaerobic sealants S9-S12 is above 300 ℃. And the anaerobic sealants S1-S12 have good flame retardance.
The anaerobic sealant disclosed by the application has good dielectric property, high thermal aging resistance, high internal pressure resistance and certain adhesion.
While the basic concepts have been described above, it will be apparent to those skilled in the art that the foregoing detailed disclosure is by way of example only and is not intended to be limiting. Although not explicitly described herein, various modifications, improvements, and adaptations of the present application may occur to one skilled in the art. Such modifications, improvements, and modifications are intended to be suggested in some embodiments of the present application, and therefore, such modifications, improvements, and modifications are intended to be included within the spirit and scope of the exemplary embodiments of the present application.
Meanwhile, the present application uses specific words to describe embodiments of the present application. Reference to "one embodiment," "an embodiment," and/or "some embodiments" means that a particular feature, structure, or characteristic is associated with at least one embodiment of the present application. Thus, it should be emphasized and should be appreciated that two or more references to "one embodiment," "an embodiment," or "an alternative embodiment" in various positions in this specification are not necessarily referring to the same embodiment. Furthermore, certain features, structures, or characteristics of one or more embodiments of the present application may be combined as suitable.
Likewise, it should be noted that in order to simplify the presentation disclosed herein and thereby aid in understanding one or more inventive embodiments, various features are sometimes grouped together in a single embodiment or description thereof. This method of disclosure, however, is not intended to imply that more features than are presented in the claims are required for the subject application. Indeed, less than all of the features of a single embodiment disclosed above.
In some embodiments, numbers describing the components, number of attributes are used, it being understood that such numbers being used in the description of embodiments are modified in some examples by the modifier "about," approximately, "or" substantially. Unless otherwise indicated, "about," "approximately," or "substantially" indicate that the number allows for a 20% variation. Accordingly, in some embodiments, numerical parameters set forth in the specification and claims are approximations that may vary depending upon the desired properties sought to be obtained by the individual embodiments. In some embodiments, the numerical parameters should take into account the specified significant digits and employ a method for preserving the general number of digits. Although the numerical ranges and parameters set forth herein are approximations that may be employed in some embodiments to confirm the breadth of the range, in particular embodiments, the setting of such numerical values is as precise as possible.
Each patent, patent application publication, and other material, such as articles, books, specifications, publications, documents, etc., cited in this application is hereby incorporated by reference in its entirety. Except for application history documents that are inconsistent or conflicting with the present application, documents that are currently or later attached to this application for which the broadest scope of the claims to the present application is limited. It is noted that the descriptions, definitions, and/or terms used in the subject matter of this application are subject to such descriptions, definitions, and/or terms if they are inconsistent or conflicting with such descriptions, definitions, and/or terms.
Finally, it should be understood that the embodiments described herein are merely illustrative of the principles of the embodiments of the present application. Other variations are also possible within the scope of this application. Thus, by way of example, and not limitation, alternative configurations of embodiments of the present application may be considered in keeping with the teachings of the present application. Accordingly, embodiments of the present application are not limited to only the embodiments explicitly described and depicted herein.
Claims (11)
1. An anaerobic sealant, characterized in that the anaerobic sealant comprises:
monomer-inhibitor mixtures; the monomer comprises a mixture of methacrylic acid organic silicon modified epoxy resin monomer, methacrylic acid hydantoin epoxy resin monomer and methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer; wherein,
the structural formula of the methacrylic acid organic silicon modified epoxy resin monomer is shown as a formula (1):
the structural formula of the hydantoin methacrylate epoxy resin monomer is shown as a formula (2):
the structural formula of the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is shown as a formula (3):
an initiator selected from one or more of organic peroxides;
a first accelerator and a second accelerator, which are respectively selected from one or more of a first amine, hydrazine and derivatives thereof, mercaptan or a first organic dibasic acid;
a co-accelerator selected from one or more of a sugar salt or a second organic dibasic acid;
a first polymerization inhibitor and a second polymerization inhibitor, which are respectively selected from one or more of phenols, quinones, oximes, azo compounds or second amines; and
a solvent;
wherein, the weight ratio of the methacrylic acid organic silicon modified epoxy resin monomer to the methacrylic acid hydantoin epoxy resin monomer to the methacrylic acid-cyclohexane-1, 2-diglycidyl ester monomer is 20-100 percent: 0-40%:0-40%; the mass ratio of the monomer-polymerization inhibitor mixture, the initiator, the first accelerator, the second accelerator, the auxiliary accelerator, the first polymerization inhibitor and the second polymerization inhibitor is 100:1.6-2.0:0.33-0.35:0.8-1.0:0.04-0.05:0.10-0.11:0.014-0.015.
2. The anaerobic sealant according to claim 1, wherein the organic peroxide comprises one or more of di-t-butyl peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, t-butyl peroxybenzoate, t-butyl pivalate peroxide, t-butyl acetate peroxide, t-butyl benzoate peroxide, and cumene peroxide.
3. The anaerobic sealant according to claim 2, wherein said organic peroxide is cumene hydroperoxide.
4. An anaerobic sealant according to claim 1 or claim 3, wherein said first amine comprises one or more of triethylamine, N-dimethylaniline, N-diethyl-p-toluidine, α -aminopyridine, 1,2,3, 4-tetrahydroquinoline, 1, 2-propanediamine, triethanolamine, dimethylamide.
5. The anaerobic sealant according to claim 4, wherein said first amine is triethylamine or N, N-dimethylaniline, said hydrazine and derivatives thereof are phenylhydrazine, said thiol is dodecyl mercaptan, and said first organic diacid is oxalic acid.
6. The anaerobic sealant according to claim 1 or claim 5, wherein said saccharin salt comprises one or more of saccharin salified with an amine, saccharin salified with 1,2,3, 4-tetrahydroquinoline, saccharin salified with 6-methyl-1, 2,3, 4-tetrahydroquinoline.
7. The anaerobic sealant according to claim 6, wherein said sugar fine salt is saccharin salified with an amine and said second organic diacid is maleic acid.
8. The anaerobic sealant according to claim 1 or claim 7, wherein said phenol is hydroquinone or N-nitrophenol, said quinone is p-benzoquinone, said oxime is p-benzoquinone dioxime, and said second amine is N-nitrosodiphenylamine or sulfurized diphenylamine.
9. The anaerobic sealant according to claim 8, further comprising a filler comprising one or more of titanium dioxide, polytetrafluoroethylene, or poly-p-phenylene benzobisoxazole.
10. The anaerobic sealant according to claim 9, wherein said solvent is methacrylic acid or acrylic acid.
11. A method of preparing an anaerobic sealant according to any of claims 1 to 10, comprising:
mixing one or more monomer-polymerization inhibitor mixture;
adding a first accelerator, a second accelerator, a first polymerization inhibitor and a second polymerization inhibitor, and stirring for a first period of time until the mixture is uniformly mixed;
adding filler and stirring for a second time period until the filler and the second time period are uniformly mixed;
and adding a second accelerator, an initiator and a solvent, and uniformly stirring until no precipitate exists to obtain the anaerobic sealant.
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US4235986A (en) * | 1979-04-02 | 1980-11-25 | National Starch And Chemical Corporation | Anaerobic curing adhesive composition and process for making same |
CN112608702A (en) * | 2020-12-03 | 2021-04-06 | 迪马新材料科技(苏州)有限公司 | Double-component acrylic acid modified epoxy adhesive and preparation process thereof |
CN114032037A (en) * | 2021-11-26 | 2022-02-11 | 迪马新材料科技(苏州)有限公司 | Anaerobic sealant and preparation method thereof |
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US4235986A (en) * | 1979-04-02 | 1980-11-25 | National Starch And Chemical Corporation | Anaerobic curing adhesive composition and process for making same |
CN112608702A (en) * | 2020-12-03 | 2021-04-06 | 迪马新材料科技(苏州)有限公司 | Double-component acrylic acid modified epoxy adhesive and preparation process thereof |
CN114032037A (en) * | 2021-11-26 | 2022-02-11 | 迪马新材料科技(苏州)有限公司 | Anaerobic sealant and preparation method thereof |
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