CN115725256A - Detachable acrylate adhesive, preparation method thereof and detachable structural member - Google Patents
Detachable acrylate adhesive, preparation method thereof and detachable structural member Download PDFInfo
- Publication number
- CN115725256A CN115725256A CN202211447283.5A CN202211447283A CN115725256A CN 115725256 A CN115725256 A CN 115725256A CN 202211447283 A CN202211447283 A CN 202211447283A CN 115725256 A CN115725256 A CN 115725256A
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- Prior art keywords
- acrylate
- methacrylate
- bond
- component
- parts
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 106
- 239000000853 adhesive Substances 0.000 title claims abstract description 106
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 106
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000243 solution Substances 0.000 claims description 41
- 230000008878 coupling Effects 0.000 claims description 28
- 238000010168 coupling process Methods 0.000 claims description 28
- 238000005859 coupling reaction Methods 0.000 claims description 28
- 239000003431 cross linking reagent Substances 0.000 claims description 27
- 239000004925 Acrylic resin Substances 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 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
- 239000011258 core-shell material Substances 0.000 claims description 15
- -1 acrylic ester Chemical class 0.000 claims description 14
- 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
- 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
- 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
- 239000002253 acid Substances 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
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- 125000005262 alkoxyamine group Chemical group 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
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-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
- 238000002156 mixing Methods 0.000 claims description 6
- 239000000178 monomer Substances 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
- 150000007854 aminals Chemical class 0.000 claims description 5
- VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 claims description 5
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 5
- 150000002905 orthoesters Chemical class 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
- 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
- 108010024636 Glutathione Proteins 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 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
- 239000000203 mixture Substances 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 238000003197 gene knockdown Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 238000004064 recycling Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 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
- 239000003513 alkali Substances 0.000 description 3
- 230000009286 beneficial effect Effects 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
- 238000012360 testing method Methods 0.000 description 3
- APTMUIAOGSSQEM-UHFFFAOYSA-N 2-(2,2-dihydroxyethyldisulfanyl)ethane-1,1-diol Chemical compound OC(O)CSSCC(O)O APTMUIAOGSSQEM-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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
- 238000004140 cleaning Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000000463 material Substances 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
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000004971 Cross linker Substances 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 group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical group OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process 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
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 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
- LIRDHUDRLFDYAI-UHFFFAOYSA-H iron(3+);trisulfite Chemical compound [Fe+3].[Fe+3].[O-]S([O-])=O.[O-]S([O-])=O.[O-]S([O-])=O LIRDHUDRLFDYAI-UHFFFAOYSA-H 0.000 description 1
- 239000004005 microsphere 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
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000005374 primary esters Chemical class 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
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
Images
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
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- 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 acrylate adhesive, and the acrylate adhesive is treated by a reducing solution to remove the connection relation between the adjacent structural members. The invention solves the problem that the components are difficult to disassemble after being bonded by using an acrylate 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 acrylate adhesive is an adhesive type with unique performance and various varieties, products with various performances can be designed according to different raw material formulas of the acrylate adhesive, and the acrylate adhesive is applied 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 of some key components. In recent years, on the premise that the requirements for high environmental protection, low energy consumption and resource recycling are higher and higher in China, the recycling of the acrylate adhesive and the disassembly and recycling of the adhered components become an extremely important research direction.
The existing acrylate adhesive is widely applied to fixing batteries and electronic products in a new energy automobile power system, but the usage amount of the acrylate adhesive is small, the value of a bonded device is often much higher than that of the acrylate adhesive, the bonding strength of the existing acrylate adhesive to components is high after the components are bonded, when the components need to be removed, a cross-linked network structure existing in the acrylate adhesive cannot be damaged through simple post-treatment, and the bonding force between the components cannot be effectively removed. The traditional method for disassembling the bonded component is to destroy a bonding interface or a bonding layer by adding thermal expansion microspheres through mechanical force or the bonding layer, so that the bonded component is disassembled, but the bonded component is easily destroyed, or acrylate adhesive is remained on the component. Especially for the fields of complex production process, high production cost and reusability after disassembly and cleaning, the disassembly and the recycling of the adhered components are more important. The difficulty in disassembling and recycling the components after the components are bonded by using acrylate adhesive is an urgent problem.
Therefore, there is a need for a removable acrylate adhesive, a method for preparing the same, and a removable structural member, which avoid the above problems of the prior art.
Disclosure of Invention
The invention aims to provide a detachable acrylate adhesive, a preparation method thereof and a detachable structural member, and solves the problem that components are difficult to detach after being bonded by using the acrylate adhesive in the prior art.
In order to achieve the purpose, the invention provides a detachable structural part which comprises a plurality of structural parts, wherein adjacent structural parts are bonded through acrylate adhesive, and the acrylate adhesive is treated by reducing solution to remove the connection relation between the adjacent structural parts.
The detachable structural part has the advantages that: and the adjacent structural members are bonded through an acrylate adhesive, and the acrylate adhesive is treated by a reducing solution to remove the connection relation between the adjacent structural members. Compared with the prior art, the invention aims at the problems that the maintenance and the disassembly of the acrylate adhesive in the existing pack structural member are difficult, a large amount of time cost and labor cost are consumed, and unnecessary material loss is increased. The invention provides a structural member bonded by adopting an acrylate adhesive, and the purpose of being detachable can be easily realized after the acrylate adhesive adopted by the structural member is treated by a reducing solution. The invention solves the problem that the components are difficult to disassemble after being bonded by using an acrylate adhesive in the prior art.
Optionally, adjacent between the structure the bonding strength of acrylate adhesive after reducing solution is handled is 0MPa, adjacent between the structure the thickness of acrylate adhesive is less than or equal to 5 millimeters, the structure includes battery PACK structure.
Optionally, the acrylate adhesive contains a cross-linking agent, and the acrylate monomer is connected with the cross-linking agent through a weak coupling bond; after the acrylate adhesive is treated by the reducing solution, the weak coupling bond is broken or recombined to reduce the bonding strength of the acrylate adhesive by 99 to 100 percent so as to realize the detachability between the adjacent structural members.
Optionally, the step of reducing solution treatment includes: and 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 bonding strength between the adjacent structural members when the structural members are bonded by the acrylate adhesive is 1-4 MPa.
Optionally, the reducing substance is at least one selected from 2-mercaptoethanol, thioglycolic 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.
Optionally, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, a total thiocarbonic acid structure, a phosphate ester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, an amine-hindered bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate bond, a peroxy bond, an o-carbonate bond, a diels alder structure, and a boroester bond.
Another object of the present invention is to provide an acrylate adhesive applied to the detachable structural member, wherein the acrylate adhesive comprises a component a and a component B;
the component A comprises first acrylate resin, core-shell particles and peroxide, the component B comprises second acrylate resin, core-shell particles, a cross-linking agent and a catalyst, and acrylate monomers are connected through weak coupling bonds to form the cross-linking agent;
the first acrylate resin accounts for 5-15 parts by weight, the core-shell particles account for 1-5 parts by weight, and the peroxide accounts for 0.01-1.3 parts by weight;
the second acrylate resin accounts for 5-15 parts by weight of the component B, the core-shell particles account for 1-5 parts by weight of the component B, the cross-linking agent accounts for 0.5-10 parts by weight of the component B, and the catalyst accounts for 0.01-0.5 part by weight of the component B;
the mass ratio of the component A to the component B is 1 (0.5-2.0).
The acrylate adhesive has the beneficial effects that: the acrylate adhesive provided by the invention adopts weak coupling bonds to combine with other components, and has strong bonding strength in the application of a structural member, particularly a PACK structural member; and after the acrylate adhesive for bonding the structural parts 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 parts are automatically separated from each other and no residual acrylate adhesive exists on the structural parts. Therefore, the method brings great convenience to the disassembly, assembly, replacement, repair and recycling of structural components, particularly power battery devices, has simple process and easy control, and is favorable for realizing industrial continuous production. The detachable acrylate adhesive has wide application prospect in the field of structural member bonding, particularly power battery device bonding.
Optionally, 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, lauryl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
Optionally, 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, lauryl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
Optionally, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, an all-thiocarbonic acid structure, a phosphate 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 primary ester acid, an acetal structure, a primary carbonate bond, a peroxy bond, an o-carbonate bond, a diels alder structure, and a boron ester bond.
Further optionally, 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 acrylate adhesive, wherein the acrylate adhesive is obtained by mixing and reacting the component A and the component B at normal temperature for 0.5-2 h, and the mass ratio of the component A to the component B is 1 (0.5-2.0).
The preparation method of the acrylate adhesive has the beneficial effects that: the preparation method is simple and suitable for mass production, and the obtained acrylate adhesive is easy to disassemble.
The invention has the beneficial effects that:
the bonded structural member can be disassembled in a nondestructive manner, so that the recycling of the structural member is facilitated, and particularly, the structural member which is complex in production process, high in production cost and reusable after disassembly and cleaning, such as the recycling of semiconductors and chips, and particularly the recycling of a power battery pack structural member; the organic solvent in the reducing solution used in the disassembly process is low-toxic, even the organic solvent is non-toxic, the environmental pollution is small, the recovery is easy, and the recovery of the acrylate resin can be realized in the organic solvent recovery process; the concentration of the reducing substances used in the disassembly process is low, the use amount is small, the disassembly efficiency is high, and the recovery and reuse cost of the adhered component can be reduced to a great extent; the adhesive can be applied to most of acrylate adhesives and can be detached for all structural parts.
Drawings
FIG. 1 is a hydrogen spectrum of a cross-linking agent according to an embodiment of the present invention;
FIG. 2 is an IR spectrum of a cross-linking agent according to an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive step based on the embodiments of the present invention, are within the scope of protection of the present invention. Unless defined otherwise, technical or scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. As used herein, the word "comprising" and similar words are intended to mean that the element or item listed before the word covers the element or item listed after the word and its equivalents, but does not exclude other elements or items.
The embodiment of the invention provides a detachable structural part which comprises a plurality of structural parts, wherein adjacent structural parts are bonded through acrylate adhesive, and the acrylate adhesive is treated by reducing solution to remove the connection relation between the adjacent structural parts.
Specifically, adjacent structural members are bonded through an acrylate adhesive, and the acrylate adhesive is treated by a reducing solution to remove the connection relationship between the adjacent structural members. Compared with the prior art, the invention aims at the problems that the maintenance and the disassembly of the acrylate adhesive in the existing pack structural member are difficult, a large amount of time cost and labor cost are consumed, and unnecessary material loss is increased. The invention provides a structural member bonded by adopting an acrylate adhesive, which can easily realize the aim of disassembly after the acrylate adhesive adopted by the structural member is treated by a reducing solution. The invention solves the problem that the components are difficult to disassemble after being bonded by using an acrylate adhesive in the prior art.
In some embodiments of the invention, the adhesive strength of the acrylate adhesive between adjacent structural members after treatment with a 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. In some 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 invention, the acrylate adhesive comprises a cross-linking agent, wherein the acrylate monomer is 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 to reduce the bonding strength of the acrylate adhesive by 99 to 100 percent so as to realize the detachability between the adjacent structural members.
In some embodiments of the invention, the step of reducing solution treatment comprises: and treating the acrylate adhesive between the adjacent structural parts 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 bonding strength between the adjacent structural parts when the structural parts are bonded by the acrylate adhesive is 1-4 MPa. 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-ethanethiol, abbreviated as ME), thioglycolic acid (Mercaptoacetic acid, abbreviated as TGA), dithiothreitol (1, 4-dithiothreitol, abbreviated as DTT), dithioerythritol (Dithioerythritol, abbreviated as DTE), reduced Glutathione (GSH), n-tributylphosphine (Tributylphosphane), tris (2-carboxyethyl) phosphate (Tris (2-carboxythienyl) phosphine Hydrochloride, TCEP), sodium borohydride, and sodium persulfate. In some specific embodiments, the reducing substance is at least one selected from the group consisting of n-tributylphosphine, sodium borohydride, and sodium persulfate. In some embodiments, DTT is abbreviated as DTT for dithiothreitol, GSH is abbreviated as GSH for reduced glutamine, and Bu is abbreviated as Bu for n-tributylphosphine 3 P, the tris (2-carboxyethyl) phosphine hydrochloride is abbreviated in English to TCEP.
In some embodiments of the present 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 examples, the N, N-dimethylformamide is abbreviated as DMF.
In some embodiments of the invention, the weak coupling bond comprises any one of an ester bond, a sulfinic acid bond, an all-thiocarbonic acid structure, a phosphate bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, a hindered amine bond, a tertiary carbamic acid, an acylhydrazone structure, a orthoester acid, an acetal structure, an orthocarbonate bond, a peroxy bond, an o-carbonate bond, a diels alder structure, and a boroester bond.
In some embodiments of the invention, the weak coupling bond comprises any one of a disulfide bond, a ketal structure, and an imine structure.
The embodiment of the invention provides an acrylate adhesive, which is applied to the detachable structural member and comprises a component A and a component B;
the component A comprises first acrylate resin, core-shell particles and peroxide, the component B comprises second acrylate resin, core-shell particles, a cross-linking agent and a catalyst, and acrylate monomers are connected through weak coupling bonds to form the cross-linking agent;
the first acrylate resin accounts for 5-15 parts by weight, the core-shell particles account for 1-5 parts by weight, and the peroxide accounts for 0.01-1.3 parts by weight;
the second acrylic ester resin accounts for 5-15 parts by weight of the component B, the core-shell particles account for 1-5 parts by weight of the component B, the cross-linking agent accounts for 0.5-10 parts by weight of the component B, and the catalyst accounts for 0.01-0.5 part by weight of the component B;
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 bonds to combine with other components, and has strong bonding strength in the application of a structural member, particularly a PACK structural member; after the acrylate adhesive for bonding the structural parts 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 parts are automatically separated from each other and no residual acrylate adhesive exists on the structural parts. Therefore, the method brings great convenience to the disassembly, assembly, replacement, repair and recycling of structural components, particularly power battery devices, has simple process and easy control, and is favorable for realizing industrial continuous production. The detachable acrylate adhesive has wide application prospect in the field of structural member bonding, particularly power battery device bonding.
In some embodiments of the present invention, the first acrylate resin is contained in an amount of any one 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 are contained 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 is contained in an amount of any one of 0.01 parts by weight, 0.05 parts by weight, 0.1 parts by weight, 0.3 parts by weight, 0.6 parts by weight, 0.7 parts by weight, 0.8 parts by weight, 0.9 parts by weight, 1.0 parts by weight, 1.1 part by weight, 1.2 parts by weight and 1.3 parts by weight, based on the mass fraction of the a component a.
In still other specific embodiments of the present invention, the second acrylate resin is included in an amount of any one 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 are included 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, the crosslinking agent is included in an amount of any one 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 is included in an amount of any one of 0.01 parts by weight, 0.05 parts by weight, 0.1 parts by weight, 0.2 parts by weight, 0.3 parts by weight, 0.4 parts by weight and 0.5 parts by weight, based on a mass fraction of the B component.
In other specific embodiments of the present invention, the mass ratio of the component a to the component B is any one of 1.
In some embodiments of the present invention, 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, lauryl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
In some embodiments of the present invention, 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, lauryl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
In some embodiments of the present invention, the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, an all-thiocarbonic acid structure, a phosphate bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal bond, a 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 boroester bond. In some 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 invention, the nucleocapsid particles comprise MZ200, MX125 and EPS-125 produced by Shenzhen Gong science and technology Limited. In some specific embodiments, the core-shell particle comprises 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 embodiments, the peroxide comprises dibenzoyl peroxide, abbreviated as BPO.
In some embodiments of the invention, the catalyst comprises ferric sulfite, sodium sulfite, triethylamine, N-dimethylaniline, N-dimethyl-p-toluidine. In some embodiments, the catalyst comprises N, N-dimethyl-p-toluidine abbreviated as DMT.
In some embodiments of the invention, the step of preparing the cross-linking agent comprises: adding methacrylic acid, a weak coupling bond compound and a polymerization inhibitor into an n-hexane solvent, reacting at 80 ℃, and then sequentially performing 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 cross-linking agent 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 solvent removal 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 acrylate adhesive, wherein an A component and a B component are mixed and react for 0.5-2 h at normal temperature to obtain the acrylate adhesive, and the mass ratio of the A component to the B component is 1 (0.5-2.0).
In particular, the preparation method is simple and suitable for mass production, and the obtained acrylate adhesive is easy to disassemble.
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 IR spectrum of a cross-linking agent according to an embodiment of the present invention.
The first preparation method of the crosslinking agent: 12.9g of methacrylic acid, 9.24g of bis-hydroxyethyl disulfide and 0.1g of hydroquinone are added into a round-bottom flask filled with 180ml of n-hexane solvent, the flask is connected with a condensation and water separation device, reaction reflux is carried out at 80 ℃ until no water is generated in a water separator, and the diethyl glycol dimethacrylate light yellow oil is obtained after alkali washing treatment, water washing treatment, solvent removal treatment and water removal treatment in sequence, wherein the yield is 67.5%. Namely, the diethylene glycol dimethacrylate disulfide prepared by the method is marked as a first crosslinking agent.
Second method of preparation of the crosslinker: adding 10.02g of bis-hydroxyethyl disulfide and 11.3g of pyridine into a round-bottom flask containing 250ml of dichloromethane solvent, stirring for 1 hour in ice-water bath, dropwise and slowly adding 14.95g of methacryloyl chloride through a separating funnel at 0 ℃, reacting for 24 hours at room temperature after the addition is finished, then washing once with 200ml of 1mol/L HCl solution and 1mol/L NaOH solution in sequence, washing twice with deionized water, and then washing with anhydrous MgSO 4 Drying, and removing the solvent by rotary evaporation to obtain the diethylene glycol dimethacrylate disulfide in light yellow oil with the yield of 60.2%. Namely, the diethylene glycol dimethacrylate disulfide prepared by the method is marked as a second crosslinking agent.
Referring to fig. 1, a (σ =6.13ppm and σ =5.59 ppm) is the peak of double bond H (two independent singlet), b (σ =4.42 ppm) is methylene hydrogen bonded to oxygen (triplet), c (σ =1.95 ppm) is methyl hydrogen peak (singlet), and d (σ =2.98 ppm) is methylene hydrogen bonded to sulfur (triplet). The infrared spectrum of diethylene glycol dimethacrylate disulfide is shown in FIG. 2, in which 1636cm is included -1 、1402cm -1 、1011cm -1 、940cm -1 Characteristic peak of C = C double bond, 1714cm -1 、1150cm -1 Characteristic absorption peak of ester group.
Example 2
The preparation method of the acrylate adhesive comprises the following steps: according to the compositions and components in Table 1, the component A and the component B are mixed and reacted at normal temperature to obtain the acrylate adhesives, which are respectively marked as samples 1-3. 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; 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; sample 3 was mixed and reacted for 1.5h, and the mass ratio of the component A to the component B of sample 3 was 1.
TABLE 1
Comparative example
And (2) component A: 10 parts of methyl methacrylate, 3.3 parts of MZ, 0.9 part of BPO; and B component: 10 parts of methyl methacrylate, 3.3 parts of MZ200, 0.2 part of DMT; and mixing the component A and the component B according to the mass ratio of 1.
And (2) component A: 10 parts of methyl methacrylate, 3.3 parts of MZ, 0.9 part of BPO; and B component: 10 parts of methyl methacrylate, 3.3 parts of MZ200, 2 parts of polyethylene glycol 400 dimethacrylate and 0.2 part of DMT; and (3) mixing the component A and the component B according to the mass ratio of 1.
And (3) testing the dissolution property: respectively putting the samples 1-3 and the comparative samples 1-2 into 6mL of prepared 0.05mol/L reducing solution for sealing treatment, 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. Results of dissolution property test: samples 1 to 3 were completely dissolved after 24 hours, and comparative samples 1 to 2 had no dissolution phenomenon, and no dissolution phenomenon was observed even after the time was prolonged.
Respectively and uniformly coating the samples 1-3 and the comparative samples 1-2 on the surface of a 1.25 x 2.5cm aluminum sheet, pressing another aluminum sheet with the same size on the surface of the aluminum sheet for bonding, wherein the thickness of the adhesive layer is 0.2mm, obtaining an aluminum sheet structural member after 30min, soaking the aluminum sheet structural member in 100mL of prepared 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 the sample is soaked for 4 hours, the aluminum sheet adhered to the samples 1-3 is automatically separated, and no residual sample exists on the surface of the aluminum sheet; whereas the aluminum sheets bonded to comparative samples 1-2 did not change significantly. Table 2 shows the tensile and shear strengths of the aluminum sheets bonded to the samples 1 to 3 and the comparative samples 1 to 2 before and after immersion in a reducing solution having a concentration of 0.05mol/L, with reference to ISO 4587-2003 for the tensile and shear strength test. The reducing solution consists of N-tributylphosphine and N, N-dimethylformamide.
TABLE 2
| Sample 1 | Sample 2 | Sample 3 | Comparative sample 1 | Comparative sample 2 | |
| 0 hour | 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 compound with weak coupling bond to the acrylate adhesive enables the structure and performance of the acrylate adhesive to be changed after the acrylate adhesive is soaked in the reducing solution, so that the acrylate adhesive is easy to detach and the adhesive does not remain on the structural member.
The foregoing examples are merely illustrative and serve to explain some of the features of the method of the present invention. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. Also, where numerical ranges are used in the claims, subranges therein are included, and variations in these ranges are also to be construed as possible being covered by the appended claims.
Claims (13)
1. The utility model provides a detachable structure spare, its characterized in that, detachable structure spare includes a plurality of structures, and is adjacent bond through the acrylic ester adhesive between the structure spare, the acrylic ester adhesive removes after reducing solution handles adjacently the relation of connection between the structure spare.
2. The demountable structure of claim 1, wherein said acrylate adhesive between adjacent said structures has a bonding strength of 0MPa after treatment with a reducing solution, said acrylate adhesive between adjacent said structures has a thickness of less than or equal to 5 mm, and said structures comprise battery PACK structures.
3. The removable structural member of claim 1 wherein the acrylate adhesive comprises a cross-linking agent formed by linking acrylate monomers with weak coupling bonds; after the acrylate adhesive is treated by the reducing solution, the weak coupling bond is broken or recombined to reduce the bonding strength of the acrylate adhesive by 99 to 100 percent so as to realize the detachability between the adjacent structural members.
4. The demountable structural member of claim 1, wherein said step of reducing solution treatment comprises: and 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 bonding strength between the adjacent structural members when the structural members are bonded by the acrylate adhesive is 1-4 MPa.
5. The detachable structural member of claim 4, wherein the reducing substance is at least one selected from the group consisting of 2-mercaptoethanol, thioglycolic acid, dithiothreitol, dithioerythritol, reduced glutathione, n-tributylphosphine, tris (2-carboxyethyl) phosphine hydrochloride, sodium borohydride, and sodium persulfate.
6. The collapsible structure of claim 4 wherein the organic solvent is selected from at least one of methylene chloride, chloroform, ethyl acetate, toluene, xylene, tetrahydrofuran, N-dimethylformamide, and acetone.
7. The knock-down feature of claim 3, wherein the weak coupling bond includes any one of an ester bond, a sulfinic acid bond, an all-thiocarbonic acid structure, a phosphoric acid ester bond, a disulfide bond, a ketal structure, an imine structure, an alkoxyamine, an aminal, a hindered amine 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 boroester bond.
8. An acrylate adhesive applied to the detachable structural member according to any one of claims 1 to 7, wherein the acrylate adhesive comprises a component A and a component B;
the component A comprises first acrylate resin, core-shell particles and peroxide, the component B comprises second acrylate resin, core-shell particles, a cross-linking agent and a catalyst, and acrylate monomers are connected through weak coupling bonds to form the cross-linking agent;
the composition comprises a component A, a component B and a component C, wherein the component A comprises 5-15 parts by weight of first acrylate resin, 1-5 parts by weight of core-shell particles and 0.01-1.3 parts by weight of peroxide;
the second acrylic ester resin accounts for 5-15 parts by weight of the component B, the core-shell particles account for 1-5 parts by weight of the component B, the cross-linking agent accounts for 0.5-10 parts by weight of the component B, and the catalyst accounts for 0.01-0.5 part by weight of the component B;
the mass ratio of the component A to the component B is 1 (0.5-2.0).
9. The acrylate adhesive of claim 8 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, lauryl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
10. The acrylate adhesive of claim 8 wherein said 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, lauryl methacrylate, glycidyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, methyl methacrylate, and trifluoroethyl methacrylate.
11. The acrylate adhesive of claim 8 wherein said weak coupling bond comprises any one of ester bond, sulfinic acid bond, all-thiocarbonic acid structure, phosphoric acid ester bond, disulfide bond, ketal structure, imine structure, alkoxyamine, aminal, hindered amine bond, tertiary carbamic acid, acylhydrazone structure, orthoester acid, acetal structure, orthocarbonate bond, peroxy bond, o-carbonate bond, diels alder structure and boroester bond.
12. The acrylate adhesive of claim 11 wherein said weak coupling bond comprises any one of a disulfide bond, a ketal structure and an imine structure.
13. The preparation method of the acrylate adhesive according to any one of claims 8 to 12, characterized in that the acrylate adhesive is obtained by mixing and reacting the component A and the component B at normal temperature for 0.5 to 2 hours, wherein the mass ratio of the component A to the component B is 1 (0.5 to 2.0).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211447283.5A CN115725256B (en) | 2022-11-18 | 2022-11-18 | Detachable acrylate adhesive, preparation method thereof and detachable structural member |
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| 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 |
| US20140194546A1 (en) * | 2011-06-02 | 2014-07-10 | Osaka City University | Easily dismantlable adhesive composition and easily dismantlable adhesive tape |
| 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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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140194546A1 (en) * | 2011-06-02 | 2014-07-10 | Osaka City University | Easily dismantlable adhesive composition and easily dismantlable adhesive tape |
| 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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