CN115725256B - Detachable acrylate adhesive, preparation method thereof and detachable structural member - Google Patents
Detachable acrylate adhesive, preparation method thereof and detachable structural member Download PDFInfo
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- CN115725256B CN115725256B CN202211447283.5A CN202211447283A CN115725256B CN 115725256 B CN115725256 B CN 115725256B CN 202211447283 A CN202211447283 A CN 202211447283A CN 115725256 B CN115725256 B CN 115725256B
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- Prior art keywords
- methacrylate
- acrylate
- bond
- adhesive
- component
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- 239000000853 adhesive Substances 0.000 title claims abstract description 106
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 106
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title abstract description 13
- -1 acrylic ester Chemical class 0.000 claims abstract description 41
- 239000000243 solution Substances 0.000 claims description 41
- 230000008878 coupling Effects 0.000 claims description 27
- 238000010168 coupling process Methods 0.000 claims description 27
- 238000005859 coupling reaction Methods 0.000 claims description 27
- 239000003431 cross linking reagent Substances 0.000 claims description 27
- 239000004925 Acrylic resin Substances 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 239000011258 core-shell material Substances 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 14
- 229920000178 Acrylic resin Polymers 0.000 claims description 13
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 10
- 150000002466 imines Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 9
- 150000002978 peroxides Chemical class 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 6
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 6
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 6
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 6
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 6
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 239000003522 acrylic cement Substances 0.000 claims description 6
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 6
- 150000007854 aminals Chemical class 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 6
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 6
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 6
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 6
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 150000002905 orthoesters Chemical class 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 4
- 108010024636 Glutathione Proteins 0.000 claims description 4
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 claims description 4
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 4
- PBVAJRFEEOIAGW-UHFFFAOYSA-N 3-[bis(2-carboxyethyl)phosphanyl]propanoic acid;hydrochloride Chemical compound Cl.OC(=O)CCP(CCC(O)=O)CCC(O)=O PBVAJRFEEOIAGW-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- HXTCWLNZDIPLCA-UHFFFAOYSA-N dodecanoic acid;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCCCCCCCCCCC(O)=O HXTCWLNZDIPLCA-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 238000004064 recycling Methods 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000009286 beneficial effect Effects 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229960003180 glutathione Drugs 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 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
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- KYNFOMQIXZUKRK-UHFFFAOYSA-N bishydroxyethyldisulfide Natural products OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- DJPJFEIWFQHVTO-UHFFFAOYSA-N 3-[bis(2-carboxyethoxy)phosphoryloxy]propanoic acid Chemical compound OC(=O)CCOP(=O)(OCCC(O)=O)OCCC(O)=O DJPJFEIWFQHVTO-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- FPNCFEPWJLGURZ-UHFFFAOYSA-L iron(2+);sulfite Chemical compound [Fe+2].[O-]S([O-])=O FPNCFEPWJLGURZ-UHFFFAOYSA-L 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WPPLKRDOKPISSC-UHFFFAOYSA-N pentyl 2,2-dimethylpropaneperoxoate Chemical compound CCCCCOOC(=O)C(C)(C)C WPPLKRDOKPISSC-UHFFFAOYSA-N 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical compound P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-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
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention provides a detachable structural member, which comprises a plurality of structural members, wherein adjacent structural members are bonded through an acrylic ester adhesive, and the acrylic ester adhesive is treated by a reducing solution to release the connection relationship between the adjacent structural members. The invention solves the problem that components are difficult to detach after being bonded by using an acrylic ester adhesive in the prior art. The invention also provides a detachable acrylate adhesive and a preparation method thereof.
Description
Technical Field
The invention relates to the technical field of acrylate adhesives, in particular to a detachable acrylate adhesive, a preparation method thereof and a detachable structural member.
Background
The acrylic ester adhesive is an adhesive type with unique performance and numerous varieties, products with various performances can be designed according to different raw material formulas of the acrylic ester adhesive, and the application relates to various fields in daily life, such as the fields of industry and agriculture, aerospace, automobiles, electronics, biomedical treatment and the like. In the industries of new energy automobiles, electronics and the like, the acrylate adhesive plays an important role in fixing, heat conduction, insulation and other special functions for some key components. In recent years, on the premise of higher and higher requirements of high environmental protection, low energy consumption and resource recycling in China, the recycling of acrylate adhesives and the disassembly and recycling of adhered components become an extremely important research direction.
The prior acrylate adhesive has been widely used for fixing batteries and electronic products in a power system of a new energy automobile, but the use amount of the acrylate adhesive is relatively small, the value of the bonded devices is often much higher than that of the acrylate adhesive, the bonding strength of the prior acrylate adhesive to the devices is higher after the bonding is finished, and when the devices are required to be dismantled, the crosslinked network structure in the acrylate adhesive cannot be broken through simple post-treatment, so that the bonding force between the devices cannot be effectively removed. The traditional method for disassembling the adhered components is to destroy the adhesive interface or adhesive layer by adding thermal expansion microspheres through mechanical force or adhesive layer, so as to disassemble the adhered components, but the adhered components are easily destroyed or acrylate adhesive remains on the components. Particularly, the disassembly and recycling of adhered components are more important for the fields of complex production process, high production cost and reusability after disassembly and cleaning. The components are difficult to disassemble and recycle after being bonded by using an acrylic ester adhesive.
Therefore, there is a need to develop a removable acrylate adhesive, a method for preparing the same, and a removable structure to avoid the above-mentioned problems in the prior art.
Disclosure of Invention
The invention aims to provide a detachable acrylate adhesive, a preparation method thereof and a detachable structural member, which solve the problem that components are difficult to detach after being bonded by the acrylate adhesive in the prior art.
In order to achieve the above purpose, the invention provides a detachable structural member, which comprises a plurality of structural members, wherein adjacent structural members are bonded through an acrylic ester adhesive, and the acrylic ester adhesive is treated by a reducing solution to release the connection relationship between the adjacent structural members.
The detachable structural member has the beneficial effects that: the adjacent structural members are bonded through an acrylic ester adhesive, and the acrylic ester adhesive is treated by a reducing solution to release the connection relationship between the adjacent structural members. Compared with the prior art, the invention has the advantages that maintenance and disassembly are difficult for the acrylate adhesive in the existing pack structural member, a great deal of time cost and labor cost are consumed, and unnecessary material loss is increased. The invention provides a structural member bonded by an acrylic ester adhesive, which can easily realize the purpose of detachability after the acrylic ester adhesive is treated by a reducing solution. The invention solves the problem that components are difficult to detach after being bonded by using an acrylic ester adhesive in the prior art.
Optionally, the bonding strength of the acrylate adhesive between adjacent structural members after being treated by the reducing solution is 0MPa, the thickness of the acrylate adhesive between adjacent structural members is less than or equal to 5 mm, and the structural members comprise battery PACK structural members.
Optionally, the acrylate adhesive contains a cross-linking agent, and acrylate monomers are connected through weak coupling bonds to form the cross-linking agent; after the acrylate adhesive is treated by the reducing solution, the weak coupling bond is broken or recombined, so that the bonding strength of the acrylate adhesive is reduced by 99% -100% to realize the detachability between the adjacent structural members.
Optionally, the step of reducing solution treatment includes: and (3) treating the acrylate adhesive between the adjacent structural members by using the reducing solution, wherein the reducing solution comprises a reducing substance and an organic solvent, the concentration of the reducing solution is 0.01-0.5 mol/L, and the adhesive strength between the adjacent structural members is 1-4 MPa when the adjacent structural members are adhered by the acrylate adhesive.
Optionally, the reducing substance is at least one selected from 2-mercaptoethanol, thioglycollic acid, dithiothreitol, dithioerythritol, reduced glutathione, n-tributylphosphine, tris (2-carboxyethyl) phosphine hydrochloride, sodium borohydride and sodium persulfate.
Optionally, the organic solvent is at least one selected from dichloromethane, chloroform, ethyl acetate, toluene, xylene, tetrahydrofuran, N-dimethylformamide and acetone.
Alternatively, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, a perfluorocarbonic acid structure, a phosphoric acid ester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an amine-blocking bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate ester bond, a peroxy bond, an orthocarbonate bond, a diels alder structure, and a boron ester bond.
Another object of the present invention is to provide an acrylate adhesive for application to the detachable structural member, the acrylate adhesive comprising a component a and a component B;
the component A comprises a first acrylic resin, core-shell particles and peroxide, the component B comprises a second acrylic resin, core-shell particles, a cross-linking agent and a catalyst, and acrylic monomers are connected through weak coupling bonds to form the cross-linking agent;
the content of the first acrylic resin is 5-15 parts by weight, the content of the core-shell particles is 1-5 parts by weight, and the content of the peroxide is 0.01-1.3 parts by weight;
the weight percentage of the second acrylic resin is 5-15 parts, the weight percentage of the core-shell particles is 1-5 parts, the weight percentage of the cross-linking agent is 0.5-10 parts, and the weight percentage of the catalyst is 0.01-0.5 parts;
the mass ratio of the component A to the component B is 1 (0.5-2.0).
The acrylic ester adhesive has the beneficial effects that: the acrylate adhesive provided by the invention combines other components by adopting weak coupling bonds, and has strong bonding strength in the application of structural members, in particular to PACK structural members; when the acrylate adhesive for bonding structural members is treated by the reducing solution, the weak coupling bond is broken or recombined, so that the structure and the performance of the acrylate adhesive are changed, the acrylate adhesive is dissolved in the reducing solution, and finally, the structural members are automatically separated from each other, and no residual acrylate adhesive exists on the structural members. Therefore, the disassembly, assembly, replacement, repair and recycling of the structural member, particularly the power battery device, are convenient for the large belt, and the process is simple and easy to control, thereby being beneficial to realizing industrial continuous production. The detachable acrylate adhesive has wide application prospect in the field of structural member bonding, in particular to the field of power battery device bonding.
Optionally, the first acrylate resin includes at least one of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, methoxyethyl methacrylate, lauric methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
Optionally, the second acrylate resin includes at least one of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, methoxyethyl methacrylate, lauric methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
Alternatively, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, a perfluorocarbonic acid structure, a phosphoric acid ester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an amine-blocking bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate ester bond, a peroxy bond, an orthocarbonate bond, a diels alder structure, and a boron ester bond.
Further alternatively, the weak coupling bond includes any one of a disulfide bond, a ketal structure, and an imine structure.
The invention also aims to provide a preparation method of the acrylic adhesive, wherein the acrylic adhesive is obtained after the component A and the component B are mixed and reacted for 0.5-2 hours at normal temperature, and the mass ratio of the component A to the component B is 1 (0.5-2.0).
The preparation method of the acrylic ester adhesive has the beneficial effects that: the preparation method is simple, and is suitable for mass production, and the obtained acrylate adhesive is easy to detach.
The invention has the beneficial effects that:
the non-destructive disassembly of the adhered structural component is beneficial to recycling of the structural component, in particular to the recycling of the structural component which has complex production process, high production cost and reusability after disassembly and cleaning, such as the recycling of semiconductors and chips, in particular to the recycling of the pack structural component of the power battery; the organic solvent in the reducing solution used in the disassembly process is low in toxicity, even the organic solvent is nontoxic, the environmental pollution is small, the recovery is easy, and the recovery of the acrylic resin can be realized in the recovery process of the organic solvent; the concentration of the reducing substances used in the disassembly process is low, the use amount is low, the disassembly efficiency is high, and the recycling cost of the bonded component can be reduced to a great extent; the adhesive can be applied to most acrylic adhesives, and can be detached for all structural members.
Drawings
FIG. 1 is a hydrogen spectrum of a cross-linking agent according to an embodiment of the present invention;
FIG. 2 is an infrared spectrum of a cross-linking agent according to an embodiment of the present invention.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. Unless otherwise defined, technical or scientific terms used herein should be given the ordinary meaning as understood by one of ordinary skill in the art to which this invention belongs. As used herein, the word "comprising" and the like means that elements or items preceding the word are included in the element or item listed after the word and equivalents thereof without precluding other elements or items.
The embodiment of the invention provides a detachable structural member, which comprises a plurality of structural members, wherein adjacent structural members are bonded through an acrylic ester adhesive, and the acrylic ester adhesive is treated by a reducing solution to release the connection relationship between the adjacent structural members.
Specifically, adjacent structural members are bonded through an acrylic ester adhesive, and the acrylic ester adhesive is treated by a reducing solution to release the connection relationship between the adjacent structural members. Compared with the prior art, the invention has the advantages that maintenance and disassembly are difficult for the acrylate adhesive in the existing pack structural member, a great deal of time cost and labor cost are consumed, and unnecessary material loss is increased. The invention provides a structural member bonded by an acrylic ester adhesive, which can easily realize the purpose of detachability after the acrylic ester adhesive is treated by a reducing solution. The invention solves the problem that components are difficult to detach after being bonded by using an acrylic ester adhesive in the prior art.
In some embodiments of the invention, the adhesive strength of the acrylate adhesive between adjacent structural members, including battery PACK structural members, after the acrylate adhesive between adjacent structural members is treated with a reducing solution is 0MPa, and the thickness of the acrylate adhesive between adjacent structural members is less than or equal to 5 millimeters. In some specific embodiments, the thickness of the acrylate adhesive between adjacent structural members is any one of 1 mm, 2mm,3 mm, 4 mm, and 5 mm.
In some embodiments of the present invention, the acrylate adhesive comprises a cross-linking agent, wherein acrylate monomers are connected by weak coupling bonds to form the cross-linking agent; after the acrylate adhesive is treated by the reducing solution, the weak coupling bond is broken or recombined, so that the bonding strength of the acrylate adhesive is reduced by 99% -100% to realize the detachability between the adjacent structural members.
In some embodiments of the invention, the step of reducing solution treatment comprises: and (3) treating the acrylate adhesive between the adjacent structural members by using the reducing solution, wherein the reducing solution comprises a reducing substance and an organic solvent, the concentration of the reducing solution is 0.01-0.5 mol/L, and the adhesive strength between the adjacent structural members is 1-4 MPa when the adjacent structural members are adhered by the acrylate adhesive. In some specific embodiments, the concentration of the reducing solution is any one of 0.01mol/L, 0.05mol/L, 0.1mol/L, 0.15mol/L, 0.2mol/L, 0.25mol/L, 0.3mol/L, 0.35mol/L, 0.4mol/L, 0.45mol/L and 0.5mol/L, and the bonding strength between adjacent structural members when bonded by the acrylate adhesive is any one of 1MPa, 2MPa, 3MPa and 4MPa.
In some embodiments of the present invention, the reducing substance is selected from at least one of 2-mercaptoethanol (2-hydroxy-1-ethane, ME), thioglycolic acid (Mercaptoacetic acid, TGA), dithiothreitol (1, 4-dithiothreitol, DTT), dithioerythritol (DTE), reduced Glutathione (GSH), n-tributylphosphine (tributylphosphine), tris (2-carboxyethyl) phosphate (Tris (2-carboxyyl) phosphine Hydrochloride, TCEP), sodium borohydride, and sodium persulfate. In some specific embodiments, the reducing substance is selected from at least one of n-tributylphosphine, sodium borohydride, and sodium persulfate. Some specific examples, the dithiothreitolEnglish is abbreviated as DTT, english of the reduced type glutathione is abbreviated as GSH, and English of the n-tributylphosphine is abbreviated as Bu 3 P, the english abbreviation of said tris (2-carboxyethyl) phosphine hydrochloride is TCEP.
In some embodiments of the invention, the organic solvent is selected from at least one of dichloromethane, chloroform, ethyl acetate, toluene, xylene, tetrahydrofuran, N-dimethylformamide, and acetone. In some specific embodiments, the organic solvent is selected from at least one of ethyl acetate and N, N-dimethylformamide. In some specific embodiments, the english language of N, N-dimethylformamide is abbreviated as DMF.
In some embodiments of the invention, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, a perfluorocarbonic acid structure, a phosphoric acid ester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an hindered amine bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate bond, a peroxy bond, an orthocarbonate bond, a diels alder structure, and a boron ester bond.
In some embodiments of the invention, the weakly coupled bond includes any one of a disulfide bond, a ketal structure, and an imine structure.
In the embodiment of the invention, an acrylic ester adhesive is provided, wherein the acrylic ester adhesive is applied to the detachable structural member and comprises a component A and a component B;
the component A comprises a first acrylic resin, core-shell particles and peroxide, the component B comprises a second acrylic resin, core-shell particles, a cross-linking agent and a catalyst, and acrylic monomers are connected through weak coupling bonds to form the cross-linking agent;
the content of the first acrylic resin is 5-15 parts by weight, the content of the core-shell particles is 1-5 parts by weight, and the content of the peroxide is 0.01-1.3 parts by weight;
the weight percentage of the second acrylic resin is 5-15 parts, the weight percentage of the core-shell particles is 1-5 parts, the weight percentage of the cross-linking agent is 0.5-10 parts, and the weight percentage of the catalyst is 0.01-0.5 parts;
the mass ratio of the component A to the component B is 1 (0.5-2.0).
Specifically, the acrylate adhesive provided by the invention adopts weak coupling bond to combine with other components, and has strong bonding strength in the application of structural members, in particular to PACK structural members; when the acrylate adhesive for bonding structural members is treated by the reducing solution, the weak coupling bond is broken or recombined, so that the structure and the performance of the acrylate adhesive are changed, the acrylate adhesive is dissolved in the reducing solution, and finally, the structural members are automatically separated from each other, and no residual acrylate adhesive exists on the structural members. Therefore, the disassembly, assembly, replacement, repair and recycling of the structural member, particularly the power battery device, are convenient for the large belt, and the process is simple and easy to control, thereby being beneficial to realizing industrial continuous production. The detachable acrylate adhesive has wide application prospect in the field of structural member bonding, in particular to the field of power battery device bonding.
In some embodiments of the present invention, the first acrylate resin may be present in an amount of 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight, 14 parts by weight, and 15 parts by weight, the core-shell particles may be present in an amount of any one of 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, and 5 parts by weight, and the peroxide may be present in an amount of any one of 0.01 part by weight, 0.05 part by weight, 0.1 part by weight, 0.3 part by weight, 0.6 part by weight, 0.7 part by weight, 0.8 part by weight, 0.9 part by weight, 1.0 part by weight, 1.1 part by weight, 1.2 parts by weight, and 1.3 parts by weight, based on the weight of the a part by weight of the component.
In still other specific embodiments of the present invention, the second acrylate resin may be present in an amount of 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, 10 parts by weight, 11 parts by weight, 12 parts by weight, 13 parts by weight, 14 parts by weight, and 15 parts by weight, the core-shell particle may be present in an amount of 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, and 5 parts by weight, the crosslinking agent may be present in an amount of 1 part by weight, 2 parts by weight, 3 parts by weight, 4 parts by weight, 5 parts by weight, 6 parts by weight, 7 parts by weight, 8 parts by weight, 9 parts by weight, and 10 parts by weight, and the catalyst may be present in an amount of 0.01 part by weight, 0.05 part by weight, 0.1 part by weight, 0.2 part by weight, 0.3 part by weight, 0.4 part by weight, and 0.5 part by weight, based on the weight of the component B.
In other embodiments of the present invention, the mass ratio of the a component to the B component is any one of 1:0.5, 1:1, 1:1.5, and 1:2.
In some embodiments of the present invention, the first acrylate resin includes at least one of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, methoxyethyl methacrylate, lauric methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
In some embodiments of the present invention, the second acrylate resin includes at least one of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, methoxyethyl methacrylate, lauric methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
In some embodiments of the invention, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, a perfluorocarbonic acid structure, a phosphoric acid ester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an hindered amine bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate bond, a peroxy bond, an orthocarbonate bond, a diels alder structure, and a boron ester bond. In some specific embodiments, the weak coupling bond includes any one of a disulfide bond, a ketal structure, and an imine structure. In some more specific embodiments, the weak coupling bond is a disulfide bond.
In some embodiments of the present invention, the core-shell particles comprise MZ200, MX125, EPS-125 manufactured by Shenzhen, inc. In some specific embodiments, the core-shell particles comprise MZ200.
In some embodiments of the invention, the peroxide comprises dibenzoyl peroxide, cumyl hydroperoxide, dilauroyl peroxide, t-butyl hydroperoxide, t-butyl peroxyacetate, dicyclohexyl peroxydicarbonate, t-butyl peroxypivalate, amyl peroxypivalate, diisopropyl peroxydicarbonate. In some specific embodiments, the peroxide comprises dibenzoyl peroxide, abbreviated as BPO.
In some embodiments of the invention, the catalyst comprises iron sulfite, sodium sulfite, triethylamine, N-dimethylaniline, N-dimethyl-p-toluidine. In some specific embodiments, the catalyst comprises N, N-dimethyl-p-toluidine, abbreviated as DMT.
In some embodiments of the invention, the step of preparing the crosslinker comprises: adding methacrylic acid, a weak coupling bond compound and a polymerization inhibitor into a normal hexane solvent for reaction at 80 ℃, and then sequentially carrying out alkali washing treatment, water washing treatment, solvent removal treatment and water removal treatment to obtain the cross-linking agent, wherein the molar ratio of the methacrylic acid to the weak coupling bond compound is (2-3): 1.
In some embodiments of the invention, the step of preparing the crosslinker comprises: adding a weak coupling bond compound and an acid binding agent into a dichloromethane solvent, stirring for 1 hour in an ice-water bath, slowly adding a methacryloyl chloride compound, reacting for 24 hours at room temperature, and then sequentially carrying out acid washing treatment, alkali washing treatment, water washing treatment, drying treatment and desolventizing treatment to obtain the cross-linking agent, wherein the molar ratio of the methacryloyl chloride compound to the acid binding agent is 1 (1-1.5).
The embodiment of the invention provides a preparation method of an acrylic ester adhesive, which is characterized in that an acrylic ester adhesive is obtained after a component A and a component B are mixed and reacted for 0.5-2 hours at normal temperature, and the mass ratio of the component A to the component B is 1 (0.5-2.0).
Specifically, the preparation method is simple, and is suitable for mass production, and the obtained acrylate adhesive is easy to detach.
Example 1
FIG. 1 is a hydrogen spectrum of a cross-linking agent according to an embodiment of the present invention; FIG. 2 is an infrared spectrum of a cross-linking agent according to an embodiment of the present invention.
The first preparation method of the cross-linking agent comprises the following steps: 12.9g of methacrylic acid, 9.24g of bishydroxyethyl disulfide and 0.1g of hydroquinone are added into a round-bottomed flask filled with 180ml of normal hexane solvent, the flask is connected with a condensation water diversion device, the reaction reflux is carried out at 80 ℃ until no water is generated in the water diversion device, and the light yellow oily diethylene glycol dimethacrylate disulfide is obtained after the alkali washing treatment, the water washing treatment, the desolventizing treatment and the water removal treatment in sequence, and the yield is 67.5%. Namely, the diethylene glycol dimethacrylate disulfide prepared by the method is marked as a first crosslinking agent.
A second preparation method of the cross-linking agent: 10.02g of bishydroxyethyl disulfide and 11.3g of pyridine are added into a round-bottomed flask filled with 250ml of dichloromethane solvent, stirred in an ice-water bath for 1 hour, 14.95g of methacryloyl chloride is slowly added dropwise through a separating funnel at 0 ℃ and reacted at room temperature for 24 hours after the addition is completed, then washed once with 200ml of 1mol/L HCl solution and 1mol/L NaOH solution in sequence, washed twice with deionized water, and finally dried over anhydrous MgSO 4 Drying and spin evaporation of the solvent gave diethylene glycol dimethacrylate as a pale yellow oil in 60.2% yield. Namely, the method prepares the disulfide diethylene glycol dimethacrylateAnd is denoted as a second crosslinking agent.
The hydrogen spectrum of diethylene glycol dimethacrylate disulfide refers to fig. 1, in which a (σ=6.13 ppm and σ=5.59 ppm) is the peak (two independent singlet) of double bond H, b (σ=4.42 ppm) is the methylene hydrogen with oxygen (triplet), c (σ=1.95 ppm) is the methyl hydrogen peak (singlet), and d (σ=2.98 ppm) is the methylene hydrogen peak with sulfur (triplet). The infrared spectrum of diethylene glycol dimethacrylate disulfide is shown in FIG. 2, which is 1636cm -1 、1402cm -1 、1011cm -1 、940cm -1 Characteristic peak of C=C double bond, 1714cm -1 、1150cm -1 Is a characteristic absorption peak of the ester group.
Example 2
The preparation method of the acrylic ester adhesive comprises the following steps: according to the compositions and components in Table 1, the A component and the B component were mixed at room temperature to obtain an acrylic adhesive, which was designated as samples 1 to 3, respectively. Mixing and reacting the sample 1 for 0.5h, wherein the mass ratio of the component A to the component B of the sample 1 is 1:0.8; mixing and reacting the sample 2 for 1.0h, wherein the mass ratio of the component A to the component B of the sample 2 is 1:1; sample 3 was mixed and reacted for 1.5 hours, and the mass ratio of the A component to the B component of sample 3 was 1:1.6.
TABLE 1
Comparative example
And (3) a component A: 10 parts of methyl methacrylate, 3.3 parts of MZ200 and 0.9 part of BPO; and the component B comprises the following components: 10 parts of methyl methacrylate, 3.3 parts of MZ200 and 0.2 part of DMT; and mixing the component A and the component B according to the mass ratio of 1:1 for reaction for 30min to obtain the acrylic adhesive, which is marked as a comparative sample 1.
And (3) a component A: 10 parts of methyl methacrylate, 3.3 parts of MZ200 and 0.9 part of BPO; and the component B comprises the following components: 10 parts of methyl methacrylate, 3.3 parts of MZ200, 2 parts of polyethylene glycol 400 dimethacrylate and 0.2 part of DMT; and mixing the component A and the component B according to the mass ratio of 1:1 for reaction for 30min to obtain the acrylic adhesive, which is marked as a comparative sample 2.
Dissolution performance test: and respectively placing the samples 1-3 and the comparative samples 1-2 into 6mL of an existing 0.05mol/L reducing solution, sealing, and observing the dissolution condition of the resin every 1h at room temperature, wherein the reducing solution consists of N-tributylphosphine and N, N-dimethylformamide. Dissolution performance test results: samples 1 to 3 were completely dissolved after 24 hours, and no dissolution phenomenon was found in comparative samples 1 to 2 even if the time was prolonged.
And uniformly coating samples 1-3 and comparative samples 1-2 on the surfaces of 1.25 x 2.5cm aluminum sheets respectively, pressing another aluminum sheet with the same size on the aluminum sheet to bond, obtaining an aluminum sheet structural member after the thickness of an adhesive layer is 0.2mm and 30min, immersing the aluminum sheet structural member in 100mL of an existing reducing solution with the concentration of 0.05mol/L, and observing the bonding condition of the aluminum sheet every 1 hour at room temperature. After soaking for 4 hours, the bonded aluminum sheets of the samples 1-3 are automatically separated, and no residual sample exists on the surfaces of the aluminum sheets; while the aluminum flakes bonded to comparative samples 1-2 did not change significantly. Table 2 shows the tensile shear strength of the aluminum sheets bonded by samples 1 to 3 and comparative samples 1 to 2 before and after immersion in a reducing solution having a concentration of 0.05mol/L, and the standard for tensile shear strength reference was ISO 4587-2003. The reducing solution consists of N-tributylphosphine and N, N-dimethylformamide.
TABLE 2
| Sample 1 | Sample 2 | Sample 3 | Comparative sample 1 | Comparative sample2 | |
| 0 hours | 2.45MPa | 2.76MPa | 3.29MPa | 2.38MPa | 2.94MPa |
| 4 hours | 0 | 0 | 0 | 2.29MPa | 2.72MPa |
As can be seen from the data in table 2, the addition of the cross-linking agent containing the weak coupling bond compound to the acrylate adhesive allows the acrylate adhesive to change the structure and properties of the acrylate adhesive after being immersed in the reducing solution, thereby allowing the acrylate adhesive to be easily removed without leaving adhesive on the structural member.
The foregoing examples are illustrative only and serve to explain some features of the method of the invention. The appended claims are intended to claim the broadest possible scope and the embodiments presented herein are merely illustrative of selected implementations based on combinations of all possible embodiments. It is, therefore, not the intention of the applicant that the appended claims be limited by the choice of examples illustrating the features of the invention. Some numerical ranges used in the claims also include sub-ranges within which variations in these ranges should also be construed as being covered by the appended claims where possible.
Claims (9)
1. The detachable structural member is characterized by comprising a plurality of structural members, wherein adjacent structural members are bonded through an acrylic ester adhesive, the acrylic ester adhesive is treated by a reducing solution to release the connection relationship between the adjacent structural members, the acrylic ester adhesive contains a cross-linking agent, and acrylic ester monomers are connected through weak coupling bonds to form the cross-linking agent; after the acrylate adhesive is treated by a reducing solution, the weak coupling bond is broken or recombined, so that the bonding strength of the acrylate adhesive is reduced by 99% -100% to realize the detachability between adjacent structural members, and the step of treating by the reducing solution comprises the following steps: the acrylate adhesive between adjacent structural members is treated by using a reducing solution, the reducing solution comprises a reducing substance and an organic solvent, the concentration of the reducing solution is 0.01-0.5 mol/L, the bonding strength of the adjacent structural members when the structural members are bonded by the acrylate adhesive is 1-4 MPa, the reducing substance is at least one selected from 2-mercaptoethanol, thioglycollic acid, dithiothreitol, dithioerythritol, reduced glutathione, N-tributylphosphine, tris (2-carboxyethyl) phosphine hydrochloride, sodium borohydride and sodium persulfate, and the organic solvent is at least one selected from dichloromethane, chloroform, ethyl acetate, toluene, xylene, tetrahydrofuran, N-dimethylformamide and acetone.
2. The removable structure of claim 1, wherein the adhesive strength of the acrylate adhesive between adjacent structures after the reductive solution treatment is 0MPa, and the thickness of the acrylate adhesive between adjacent structures is less than or equal to 5 millimeters, the structure comprising a battery PACK structure.
3. The detachable structural member of claim 1, wherein the weak coupling bond comprises any one of an ester bond, a sulfinic acid bond, a perfluorocarbonic acid structure, a phosphoester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an hindered amine bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate bond, a peroxy bond, an orthocarbonate bond, a diels alder structure, and a boron bond.
4. An acrylic adhesive, characterized in that it is applied to the detachable structural member according to any one of claims 1 to 3, and comprises a component a and a component B;
the component A comprises a first acrylic resin, core-shell particles and peroxide, the component B comprises a second acrylic resin, core-shell particles, a cross-linking agent and a catalyst, and acrylic monomers are connected through weak coupling bonds to form the cross-linking agent;
the weight percentage of the component A is calculated, the content of the first acrylic resin is 5-15 parts by weight, the content of the core-shell particles is 1-5 parts by weight, and the content of the peroxide is 0.01-1.3 parts by weight;
the weight percentage of the second acrylic resin is 5-15 parts, the weight percentage of the core-shell particles is 1-5 parts, the weight percentage of the cross-linking agent is 0.5-10 parts, and the weight percentage of the catalyst is 0.01-0.5 parts;
the mass ratio of the component A to the component B is 1 (0.5-2.0).
5. The acrylate adhesive of claim 4 wherein the first acrylate resin comprises at least one of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, methoxyethyl methacrylate, laurate methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, and trifluoroethyl methacrylate.
6. The acrylate adhesive of claim 4 wherein the second acrylate resin comprises at least one of acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, cyclohexyl methacrylate, phenoxyethyl methacrylate, methoxyethyl methacrylate, laurate methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, and trifluoroethyl methacrylate.
7. The acrylate adhesive of claim 4 wherein the weak coupling bond comprises any one of an ester bond, a sulfinic acid bond, a perfluorocarbonic acid structure, a phosphoester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an amine blocking bond, a tertiary carbamate, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate bond, a peroxy bond, an orthocarbonate bond, a diels alder structure, and a boron bond.
8. The acrylate adhesive of claim 7 wherein said weak coupling bond comprises any one of a disulfide bond, a ketal structure, and an imine structure.
9. The method for preparing the acrylate adhesive according to any one of claims 4 to 8, wherein the acrylate adhesive is obtained by mixing and reacting the component A and the component B for 0.5 to 2 hours at normal temperature, and the mass ratio of the component A to the component B is 1 (0.5 to 2.0).
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103797082A (en) * | 2011-09-14 | 2014-05-14 | 电气化学工业株式会社 | Composition and method for temporarily fixing member using same |
| WO2015093517A1 (en) * | 2013-12-17 | 2015-06-25 | 住友化学株式会社 | Aqueous emulsion |
| CN111334214A (en) * | 2020-03-24 | 2020-06-26 | 广东硕成科技有限公司 | Novel protective film containing thermal viscosity-reducing adhesive and preparation method thereof |
| CN111363481A (en) * | 2019-12-23 | 2020-07-03 | 烟台信友新材料有限公司 | Low-shrinkage, low-modulus and heat-resistant UV-heat dual-curing adhesive and preparation method thereof |
| CN114752342A (en) * | 2021-05-19 | 2022-07-15 | 道生天合材料科技(上海)股份有限公司 | Acrylate adhesive and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI535814B (en) * | 2011-06-02 | 2016-06-01 | 迪愛生股份有限公司 | Easily-disassemble adhesive composition and easily-disassemble adhesive tape |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103797082A (en) * | 2011-09-14 | 2014-05-14 | 电气化学工业株式会社 | Composition and method for temporarily fixing member using same |
| WO2015093517A1 (en) * | 2013-12-17 | 2015-06-25 | 住友化学株式会社 | Aqueous emulsion |
| CN111363481A (en) * | 2019-12-23 | 2020-07-03 | 烟台信友新材料有限公司 | Low-shrinkage, low-modulus and heat-resistant UV-heat dual-curing adhesive and preparation method thereof |
| CN111334214A (en) * | 2020-03-24 | 2020-06-26 | 广东硕成科技有限公司 | Novel protective film containing thermal viscosity-reducing adhesive and preparation method thereof |
| CN114752342A (en) * | 2021-05-19 | 2022-07-15 | 道生天合材料科技(上海)股份有限公司 | Acrylate adhesive and preparation method thereof |
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