JPH11504625A - オルガノボランポリオキシアルキレンポリアミン錯体および該錯体を用いて製造された接着剤組成物 - Google Patents
オルガノボランポリオキシアルキレンポリアミン錯体および該錯体を用いて製造された接着剤組成物Info
- Publication number
- JPH11504625A JPH11504625A JP8531000A JP53100096A JPH11504625A JP H11504625 A JPH11504625 A JP H11504625A JP 8531000 A JP8531000 A JP 8531000A JP 53100096 A JP53100096 A JP 53100096A JP H11504625 A JPH11504625 A JP H11504625A
- Authority
- JP
- Japan
- Prior art keywords
- complex
- organoborane
- composition
- carbon atoms
- polyamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 150
- 229920000768 polyamine Polymers 0.000 title claims abstract description 94
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 92
- 239000000853 adhesive Substances 0.000 title claims abstract description 90
- 239000000178 monomer Substances 0.000 claims abstract description 74
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 36
- 230000000977 initiatory effect Effects 0.000 claims abstract description 10
- -1 methacrylate ester Chemical class 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 37
- 150000001412 amines Chemical class 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 229910052796 boron Inorganic materials 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000004698 Polyethylene Substances 0.000 claims description 14
- 239000004743 Polypropylene Substances 0.000 claims description 14
- 229920000573 polyethylene Polymers 0.000 claims description 14
- 229920001155 polypropylene Polymers 0.000 claims description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 239000002131 composite material Substances 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- 239000003505 polymerization initiator Substances 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 239000003607 modifier Substances 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 3
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000806 elastomer Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 description 18
- 229920003023 plastic Polymers 0.000 description 16
- 239000004033 plastic Substances 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 239000012790 adhesive layer Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
- 125000004386 diacrylate group Chemical group 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 239000003522 acrylic cement Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000005304 joining Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229920002681 hypalon Polymers 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 description 1
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- MYOQCFLQFOILQC-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phthalic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O MYOQCFLQFOILQC-UHFFFAOYSA-N 0.000 description 1
- 229910000547 2024-T3 aluminium alloy Inorganic materials 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- JVUAYVUZADWJBK-UHFFFAOYSA-N 3-cyanopropyl prop-2-enoate Chemical compound C=CC(=O)OCCCC#N JVUAYVUZADWJBK-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
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- C07—ORGANIC CHEMISTRY
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
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- 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
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- Y10T428/31544—Addition polymer is perhalogenated
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- 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
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- 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
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 独占的所有権または特権を請求する実施態様を以下に規定する。 1.オルガノボランおよびポリオキシアルキレンポリアミンを含有する錯体。 2.前記オルガノボランが、構造式: 〔式中、 R1は、1個〜10個の炭素原子を有するアルキル基であり; R2およびR3は、1個〜10個の炭素原子を有するアルキル基およびフェニル含 有基から独立に選ばれる〕 で表される請求項1に記載の錯体。 3.前記ポリオキシアルキレンポリアミンが、 H2NR4O-(R5O)w-(R6O)x-(R5O)y-R4NH2 および [H2NR4O-(R5O)w]z-R7 〔式中、 R4、R5、およびR6は、1個〜10個の炭素原子を有するアルキレン基であり 、しかも同じであっても異なっていてもよく; R7はポリオールの残基であり; wは≧1であり; xは≧0であり; yは≧0であり; zは>2である〕 から成る群より選ばれる構造を有する請求項1の錯体。 4.オルガノボランおよびポリオキシアルキレンポリアミンを含 有し、かつ構造式: 〔式中、 R1は、1個〜10個の炭素原子を有するアルキル基であり; R2およびR3は、1個〜10個の炭素原子を有するアルキル基およびフェニル含 有基から独立に選ばれ; Amはポリオキシアルキレンポリアミンであり、かつ H2NR4O-(R5O)w-(R6O)x-(R5O)y-R4NH2 および [H2NR4O-(R5O)w]z-R7 (但し、 R4、R5、およびR6は、1個〜10個の炭素原子を有するアルキレン基であり 、しかも同じであっても異なっていてもよく; R7はポリオールの残基であり; w、x、およびyの値は、このオルガノボランポリアミン錯体が室温で液体で あるように選択され; zは3または4である) から成る群より選ばれる構造を有し; vの値は、この錯体中の窒素原子とホウ素原子との有効比を提供するように選 択される〕 で表されるオルガノボランポリアミン錯体。 5.R1、R2、およびR3が、1個〜5個の炭素原子を有するアルキル基から 独立に選ばれる請求項4に記載のオルガノボランポリアミン錯体。 6.R1、R2、およびR3が同じである請求項5に記載のオルガノボランポリ アミン錯体。 7.R4が2個〜4個の炭素原子を有するアルキル基であり、R5が2個〜3個 の炭素原子を有するアルキル基であり、R6が2個〜3個の炭素原子を有するア ルキル基である請求項4に記載のオルガノボランポリアミン錯体。 8.前記ポリオキシアルキレンポリアミンが約5,000未満の分子量を有する請 求項4に記載のオルガノボランポリアミン錯体。 9.前記ポリオキシアルキレンポリアミンが約250〜1,000の分子量を有する請 求項8に記載のオルガノボランポリアミン錯体。 10.前記vの値が0.1〜zである請求項4に記載のオルガノボランポリアミ ン錯体。 11.前記錯体中の窒素原子とホウ素原子との比が約1:1〜4:1である請求項4 に記載のオルガノボランポリアミン錯体。 12.前記錯体中の窒素原子とホウ素原子との比が約1:1である請求項11に 記載のオルガノボランポリアミン錯体。 13.オルガノボランおよびポリオキシアルキレンポリアミンを含有し、かつ 構造式: 〔式中、 R1、R2、およびR3は、1個〜5個の炭素原子を有するアルキル基であり、 しかも同じであり; Amはポリオキシアルキレンポリアミンであり、かつ H2NR4O-(R5O)w-(R6O)x-(R5O)y-R4NH2 および [H2NR4O-(R5O)w]z-R7 (但し、 R4は2個〜4個の炭素原子を有するアルキル基であり; R5は2個または3個の炭素原子を有するアルキル基であり; R6は2個または3個の炭素原子を有するアルキル基であり; R7はポリオールの残基であり; w、x、およびyの値は、このオルガノボランポリアミン錯体が室温で液体で あるように選択され; zは3または4である) から成る群より選ばれる構造を有し; vの値は、この錯体中の窒素原子とホウ素原子との比が約1:1〜2:1となるよう に選択される〕 で表されるオルガノボランポリアミン錯体。 14.アクリル系モノマーの重合を開始することが可能な系であって、しかも a)オルガノボランおよびポリオキシアルキレンポリアミンを含有する錯体と 、 b)アミンと反応して該オルガノボランを遊離する有効量の化合物と、 を含んでなる前記系。 15.前記錯体が、構造式: 〔式中、 R1は、1個〜10個の炭素原子を有するアルキル基であり; R2およびR3は、1個〜10個の炭素原子を有するアルキル基およびフェニル含 有基から独立に選ばれ; Amはポリオキシアルキレンポリアミンであり、かつ H2NR4O-(R5O)w-(R6O)x-(R5O)y-R4NH2 および [H2NR4O-(R5O)w]z-R7 (但し、 R4、R5、およびR6は、1個〜10個の炭素原子を有するアルキレン基であり 、しかも同じであっても異なっていてもよく; R7はポリオールの残基であり; wは≧1であり; xは≧0であり; yは≧0であり; zは>2である) から成る群より選ばれる構造を有し; vの値は、この錯体中の窒素原子とホウ素原子との有効比を提供するように選 択される〕 で表される請求項14に記載の系。 16.R1、R2、およびR3は、1個〜5個の炭素原子を有するアルキル基で あり、しかも同じであり; R4は2個〜4個の炭素原子を有するアルキル基であり; R5は2個または3個の炭素原子を有するアルキル基であり; R6は2個または3個の炭素原子を有するアルキル基であり; R7はポリオールの残基であり; w、x、およびyの値は、前記オルガノボランポリアミン錯体が室温で液体で あるように選択され; zは3または4であり; vの値は、前記錯体中のホウ素原子と窒素原子との比が約1:1〜2:1となるよう に選択される請求項15に記載の系。 17.アミンと反応する前記化合物が、イソシアネート、酸、酸クロリド、ス ルホニルクロリド、およびアルデヒドから成る群より選ばれる請求項14に記載 の系。 18.アミンと反応する前記化合物が、アクリル酸またはメタクリル酸である 請求項16に記載の系。 19.a)少なくとも1つのアクリル系モノマーと、 b)オルガノボランおよびポリオキシアルキレンポリアミンを含有する有効量 の錯体と、 c)アミンと反応してオルガノボランを遊離し、少なくとも1つのアクリル系 モノマーの重合を開始する有効量の化合物と、 を含んでなる重合性アクリル系組成物。 20.前記の少なくとも1つのアクリル系モノマーが、単官能性アクリレート エステル、単官能性メタクリレートエステル、これらの置換誘導体、および以上 のモノマーのブレンドから成る群より選ばれる請求項19に記載の重合性アクリ ル系組成物。 21.前記単官能性メタクリレートエステルが、メチルメタクリレート、エチ ルメタクリレート、メトキシエチルメタクリレート、ヒドロキシエチルメタクリ レート、ヒドロキシプロピルメタクリレート、シクロヘキシルメタクリレート、 テトラヒドロフルフリルメタクリレート、およびこれらのブレンドから成る群よ り選ばれる請求項20に記載の重合性アクリル系組成物。 22.前記の少なくとも1つのアクリル系モノマーが、アルキルメタクリレー トとアルキルアクリレートとのブレンドを含む請求項19に記載の重合性アクリ ル系組成物。 23.前記アルキルメタクリレートがメチルメタクリレートであり、かつ前記 アルキルアクリレートがブチルアクリレートである請求項22に記載の重合性ア クリル系組成物。 24.エラストマー改質剤を更に含んでなる請求項19に記載の重合性アクリ ル系組成物。 25.前記組成物が約0.03重量%〜1.5重量%のホウ素を含有する 請求項19に記載の重合性アクリル系組成物。 26.前記組成物が約0.1重量%〜0.3重量%のホウ素を含有する請求項25に 記載の重合性アクリル系組成物。 27.アミンと反応する前記化合物が、酸、イソシアネート、酸クロリド、ス ルホニルクロリド、およびアルデヒドから成る群より選ばれる請求項19に記載 の重合性アクリル系組成物。 28.前記錯体が、構造式: 〔式中、 R1は、1個〜10個の炭素原子を有するアルキル基であり; R2およびR3は、1個〜10個の炭素原子を有するアルキル基およびフェニル含 有基から独立に選ばれ; Amはポリオキシアルキレンポリアミンであり、かつ H2NR4O-(R5O)w-(R6O)x-(R5O)y-R4NH2 および [H2NR4O-(R5O)w]z-R7 (但し、 R4、R5、およびR6は、1個〜10個の炭素原子を有するアルキレン基であり 、しかも同じであっても異なっていてもよく; R7はポリオールの残基であり; wは≧1であり; xは≧0であり; yは≧0であり; zは>2である) から成る群より選ばれる構造を有し; vの値は、この錯体中の窒素原子とホウ素原子との有効比を提供 するように選択される〕 で表される請求項19に記載の重合性アクリル系組成物。 29.アミンと反応する前記化合物が酸である請求項28に記載の重合性アク リル系組成物。 30.前記酸がルイス酸またはカルボン酸である請求項29に記載の重合性ア クリル系組成物。 31.アミンと反応する前記化合物がアクリル酸またはメタクリル酸である請 求項28に記載の重合性アクリル系組成物。 32.第1の支持体と、該第1の支持体に接着剤で接合された第2の支持体と を含んでなる複合製品であって、しかも該接着剤が請求項19の重合されたアク リル系組成物を含有する前記複合製品。 33.前記第1の支持体が低表面エネルギーポリマーである請求項32に記載 の接合された複合物。 34.前記第1の支持体が、ポリエチレン、ポリプロピレン、およびポリテト ラフロオロエチレンから成る群より選ばれる請求項33に記載の接合された複合 物。 35.a)アルキルアクリレートモノマーおよびアルキルメタクリレートモノ マーを含有するアクリル系モノマーのブレンドと、 b)構造式: 〔式中、 R1は、1個〜10個の炭素原子を有するアルキル基であり; R2およびR3は、1個〜10個の炭素原子を有するアルキル基およびフェニル含 有基から独立に選ばれ; Amはポリオキシアルキレンポリアミンであり、かつ H2NR4O-(R5O)w-(R6O)x-(R5O)y-R4NH2 および [H2NR4O-(R5O)w]z-R7 (但し、 R4、R5、およびR6は、1個〜10個の炭素原子を有するアルキレン基であり 、しかも同じであっても異なっていてもよく; R7はポリオールの残基であり; w、x、およびyの値は、このオルガノボランポリアミン錯体が室温で液体で あるように選択され; zは3または4である) から成る群より選ばれる構造を有し; vの値は、この錯体中の窒素原子とホウ素原子との比が約1:1〜2:1になるよう に選択される〕 を有するオルガノボランポリアミン錯体と、 c)この錯体中のオルガノボランを遊離して該アクリル系モノマーの重合を開 始するための有効量のアクリル酸またはメタクリル酸と、 を含んでなる重合性アクリル系組成物。 36.約0.03重量%〜1.5重量%のホウ素を含有する請求項35に記載の重合 性アクリル系組成物。 37.約0.1重量%〜0.3重量%のホウ素を含有する請求項36に記載の重合性 アクリル系組成物。 38.第1の支持体と、該第1の支持体に接着剤で接合された第2の支持体と を含んでなる複合製品であって、しかも該接着剤が請求項35の重合されたアク リル系組成物を含有する前記複合製品。 39.前記第1の支持体が低表面エネルギーポリマーである請求項38に記載 の接合された複合物。 40.前記第1の支持体が、ポリエチレン、ポリプロピレン、お よびポリテトラフロオロエチレンから成る群より選ばれる請求項39に記載の接 合された複合物。 41.前記第2の支持体が、ポリエチレン、ポリプロピレン、およびポリテト ラフロオロエチレンから成る群より選ばれる請求項40に記載の接合された複合 物。 42.アクリル系モノマーの重合を開始する方法であって、しかも a)少なくとも1つのアクリル系モノマーを提供する工程と、 b)この少なくとも1つのアクリル系モノマーを重合性開始剤系とブレンドす る工程(ただし、該重合開始剤系は、 i)オルガノボランおよびポリオキシアルキレンポリアミンを含有する錯体 と、 ii)アミンと反応して該オルガノボランを遊離し、前記の少なくとも1つの アクリル系モノマーの重合を開始する有効量の化合物と、 を含む)と、 c)前記の少なくとも1つのアクリル系モノマーの重合を開始する工程と、 を含む前記方法。 43.低表面エネルギーポリマーを支持体に接合する方法であって、しかも a)低表面エネルギーポリマーを提供する工程と、 b)支持体を提供する工程と、 c)i)少なくとも1つのアクリル系モノマーと、 ii)オルガノボランおよびポリオキシアルキレンポリアミンを含有する有 効量の錯体と、 iii)アミンと反応して該オルガノボランを遊離し、前記の少 なくとも1つのアクリル系モノマーの重合を開始する有効量の化合物と、 を含む接着剤組成物を提供する工程と、 d)前記接着剤組成物を前記低表面エネルギーポリマーまたは前記支持体のい ずれかに塗布する工程と、 e)前記低表面エネルギーポリマーおよび前記支持体を、それらの間に前記接 着剤組成物を配置して結合する工程と、 f)前記接着剤組成物を硬化させて前記低表面エネルギーポリマーを前記支持 体に接着させる工程と、 を含む前記方法。
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US08/422,429 US5621143A (en) | 1995-04-14 | 1995-04-14 | Organoborane polyoxyalkylenepolyamine complexes and adhesive compositions made therewith |
PCT/US1996/003026 WO1996032398A1 (en) | 1995-04-14 | 1996-03-06 | Organoborane polyoxyalkylenepolyamine complexes and adhesive compositions made therewith |
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- 1995-04-14 US US08/422,429 patent/US5621143A/en not_active Expired - Lifetime
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- 1996-03-06 BR BR9604815A patent/BR9604815A/pt not_active IP Right Cessation
- 1996-03-06 WO PCT/US1996/003026 patent/WO1996032398A1/en active IP Right Grant
- 1996-03-06 DE DE69607953T patent/DE69607953T2/de not_active Expired - Fee Related
- 1996-03-06 DK DK96909586T patent/DK0820459T3/da active
- 1996-03-06 CN CNB991187288A patent/CN1165590C/zh not_active Expired - Fee Related
- 1996-03-06 EP EP96909586A patent/EP0820459B1/en not_active Expired - Lifetime
- 1996-03-06 JP JP53100096A patent/JP3928072B2/ja not_active Expired - Fee Related
- 1996-03-06 CA CA002216287A patent/CA2216287A1/en not_active Abandoned
- 1996-03-06 AU AU53027/96A patent/AU5302796A/en not_active Abandoned
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2002540228A (ja) * | 1999-03-19 | 2002-11-26 | スリーエム イノベイティブ プロパティズ カンパニー | オルガノボランアミン錯体開始剤システムおよびこれを用いて製造される重合性組成物 |
JP2012158767A (ja) * | 2000-03-15 | 2012-08-23 | Three M Innovative Properties Co | 結合性組成物及び結合複合品 |
JP2005500943A (ja) * | 2001-08-23 | 2005-01-13 | ダウ グローバル テクノロジーズ インコーポレイティド | 燃料タンク |
WO2015151222A1 (ja) * | 2014-03-31 | 2015-10-08 | リンテック株式会社 | 両面粘着シート |
JPWO2015151222A1 (ja) * | 2014-03-31 | 2017-04-13 | リンテック株式会社 | 両面粘着シート |
WO2016171253A1 (ja) * | 2015-04-23 | 2016-10-27 | 日立化成株式会社 | 接着剤組成物及び接続構造体 |
JPWO2016171253A1 (ja) * | 2015-04-23 | 2018-02-15 | 日立化成株式会社 | 接着剤組成物及び接続構造体 |
WO2019240277A1 (ja) * | 2018-06-15 | 2019-12-19 | デンカ株式会社 | 組成物 |
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CN1165590C (zh) | 2004-09-08 |
US5681910A (en) | 1997-10-28 |
DE69607953D1 (de) | 2000-05-31 |
DE69607953T2 (de) | 2001-06-13 |
EP0820459B1 (en) | 2000-04-26 |
EP0820459A1 (en) | 1998-01-28 |
CN1181086A (zh) | 1998-05-06 |
BR9604815A (pt) | 1998-06-09 |
CA2216287A1 (en) | 1996-10-17 |
JP3928072B2 (ja) | 2007-06-13 |
US5718977A (en) | 1998-02-17 |
DK0820459T3 (da) | 2000-08-28 |
WO1996032398A1 (en) | 1996-10-17 |
CN1259554A (zh) | 2000-07-12 |
CN1055695C (zh) | 2000-08-23 |
US5621143A (en) | 1997-04-15 |
MX9707865A (es) | 1997-11-29 |
AU5302796A (en) | 1996-10-30 |
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