JPH11503729A - オルガノボランポリアミン錯体およびそれを用いて作製した接着組成物 - Google Patents
オルガノボランポリアミン錯体およびそれを用いて作製した接着組成物Info
- Publication number
- JPH11503729A JPH11503729A JP8530999A JP53099996A JPH11503729A JP H11503729 A JPH11503729 A JP H11503729A JP 8530999 A JP8530999 A JP 8530999A JP 53099996 A JP53099996 A JP 53099996A JP H11503729 A JPH11503729 A JP H11503729A
- Authority
- JP
- Japan
- Prior art keywords
- complex
- polyamine
- organoborane
- group
- carbon atoms
- 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 147
- 229920000768 polyamine Polymers 0.000 title claims abstract description 131
- 239000000853 adhesive Substances 0.000 title claims abstract description 105
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 105
- 239000000178 monomer Substances 0.000 claims abstract description 92
- 239000000463 material Substances 0.000 claims abstract description 87
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 85
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 42
- 150000001412 amines Chemical class 0.000 claims abstract description 39
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 21
- -1 alkyl diamines Chemical class 0.000 claims description 69
- 239000000758 substrate Substances 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 150000003141 primary amines Chemical class 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052796 boron Inorganic materials 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 16
- 125000000962 organic group Chemical group 0.000 claims description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 15
- 239000004743 Polypropylene Substances 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 229920001155 polypropylene Polymers 0.000 claims description 14
- 229920003229 poly(methyl methacrylate) Chemical class 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 239000004698 Polyethylene Substances 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229920000573 polyethylene Polymers 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 230000000977 initiatory effect Effects 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- 150000002118 epoxides Chemical class 0.000 claims description 7
- 150000001414 amino alcohols Chemical class 0.000 claims description 6
- 150000001805 chlorine compounds Chemical class 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 239000000047 product Substances 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 5
- 230000007613 environmental effect Effects 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 5
- 239000003607 modifier Substances 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 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
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 claims description 2
- 229920006397 acrylic thermoplastic Chemical class 0.000 claims description 2
- 239000000806 elastomer Substances 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical class CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 7
- 150000001735 carboxylic acids Chemical class 0.000 claims 6
- 238000010276 construction Methods 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 239000001257 hydrogen Substances 0.000 description 19
- 238000002156 mixing Methods 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 16
- 150000004985 diamines Chemical class 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 229920003023 plastic Polymers 0.000 description 14
- 239000004033 plastic Substances 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 12
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 239000004926 polymethyl methacrylate Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 239000008204 material by function Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 9
- 239000003522 acrylic cement Substances 0.000 description 8
- 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 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910000085 borane Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229920000307 polymer substrate Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229920002681 hypalon Polymers 0.000 description 3
- 239000003112 inhibitor Substances 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
- 239000000376 reactant Substances 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- 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
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-UHFFFAOYSA-N 0.000 description 2
- GQRDCAVTIHMGIX-UHFFFAOYSA-N CC(C(=O)O)=C.C(C=C/C(=O)O)(=O)O.CC(C(=O)O)=C Chemical compound CC(C(=O)O)=C.C(C=C/C(=O)O)(=O)O.CC(C(=O)O)=C GQRDCAVTIHMGIX-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 241000239366 Euphausiacea Species 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVFXZWVENBQYJB-UHFFFAOYSA-N N=C=O.OC(=C)C(O)=O Chemical compound N=C=O.OC(=C)C(O)=O VVFXZWVENBQYJB-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000562 Poly(ethylene adipate) Polymers 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 238000004026 adhesive bonding Methods 0.000 description 2
- 125000002877 alkyl aryl 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
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000039 congener Substances 0.000 description 2
- 229940120693 copper naphthenate Drugs 0.000 description 2
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000004821 distillation Methods 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
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000004615 ingredient Substances 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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 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
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 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
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 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
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 description 1
- KTLBBXJRGHMTFL-UAIGNFCESA-N (Z)-but-2-enedioic acid prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)\C=C/C(O)=O KTLBBXJRGHMTFL-UAIGNFCESA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FCHKTHPTOTXBHC-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;2-methylprop-2-enoylperoxycarbonyl 2-methylprop-2-eneperoxoate Chemical compound OCCOCCO.CC(=C)C(=O)OOC(=O)OOC(=O)C(C)=C FCHKTHPTOTXBHC-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
- 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 description 1
- NHFHIOZDNXRYFF-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethanol;prop-1-ene Chemical group CC=C.OCCOCCOCCO NHFHIOZDNXRYFF-UHFFFAOYSA-N 0.000 description 1
- UFEURQXVJUNYBY-UHFFFAOYSA-N 2-[2-(2-oxoethyl)phenyl]acetaldehyde Chemical compound O=CCC1=CC=CC=C1CC=O UFEURQXVJUNYBY-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
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 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
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- WWMIMRADNBGDHP-UHFFFAOYSA-N 2-hydroxyhexanedial Chemical compound O=CC(O)CCCC=O WWMIMRADNBGDHP-UHFFFAOYSA-N 0.000 description 1
- ZTNGCTJWMNWLQA-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COCCOC(=O)C(C)=C ZTNGCTJWMNWLQA-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- 229910000547 2024-T3 aluminium alloy Inorganic materials 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
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-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
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- KPYZDEZASWILLC-UHFFFAOYSA-N B.C=C.C=C.C=C Chemical compound B.C=C.C=C.C=C KPYZDEZASWILLC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- GWZMNIRZQPRPPL-UHFFFAOYSA-N C(C=C)(=O)OCCCC#N.C(C=C)(=O)O Chemical compound C(C=C)(=O)OCCCC#N.C(C=C)(=O)O GWZMNIRZQPRPPL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- STPKQGLDXJIKGA-UHFFFAOYSA-N N=C=O.NOC(=O)C=C Chemical compound N=C=O.NOC(=O)C=C STPKQGLDXJIKGA-UHFFFAOYSA-N 0.000 description 1
- YCCCTDWBNCWPAX-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C1=CC=CC=C1C(O)=O Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C1=CC=CC=C1C(O)=O YCCCTDWBNCWPAX-UHFFFAOYSA-N 0.000 description 1
- IUEWVGUBASRSCO-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)CCCCC(O)=O Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)CCCCC(O)=O IUEWVGUBASRSCO-UHFFFAOYSA-N 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010033425 Pain in extremity Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- IWLUPSMJVLMCSV-UHFFFAOYSA-N cumene hydrogen peroxide 2-methylprop-2-enoic acid Chemical compound OO.CC(=C)C(O)=O.CC(C)C1=CC=CC=C1 IWLUPSMJVLMCSV-UHFFFAOYSA-N 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- JXXCPWUGEAFMIY-UHFFFAOYSA-N decanedioic acid 2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OC(=O)CCCCCCCCC(O)=O JXXCPWUGEAFMIY-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- OWMBTIRJFMGPAC-UHFFFAOYSA-N dimethylamino 2-methylprop-2-enoate Chemical compound CN(C)OC(=O)C(C)=C OWMBTIRJFMGPAC-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- VDNIAWMDRDWBFK-UHFFFAOYSA-N ethane-1,2-diamine;tributylborane Chemical compound NCCN.CCCCB(CCCC)CCCC VDNIAWMDRDWBFK-UHFFFAOYSA-N 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- DHPPBQGPYPPLAE-UHFFFAOYSA-N hexanedioic acid;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OC(=O)CCCCC(O)=O DHPPBQGPYPPLAE-UHFFFAOYSA-N 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- XOYONZYDWNTDAL-UHFFFAOYSA-N n-butoxyprop-2-enamide Chemical compound CCCCONC(=O)C=C XOYONZYDWNTDAL-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical class C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- IQDQMRZGMILNMQ-UHFFFAOYSA-N naphthalene-2,6-dicarbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(C=O)=CC=C21 IQDQMRZGMILNMQ-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHDYEBDPUDGIGM-UHFFFAOYSA-N oxaldehyde;propanedial Chemical compound O=CC=O.O=CCC=O BHDYEBDPUDGIGM-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WWFIYJKRQSPBLK-UHFFFAOYSA-N oxolan-2-ylmethyl 2-chloroprop-2-enoate Chemical compound ClC(=C)C(=O)OCC1CCCO1 WWFIYJKRQSPBLK-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- ZFACJPAPCXRZMQ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O ZFACJPAPCXRZMQ-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007660 shear property test Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000000992 sputter etching Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- 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
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
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)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.オルガノボランおよびポリアミンを含む錯体であって、前記ポリアミンは ジ第一級アミン末端材料と、第一級アミンと反応性の基を少なくとも2個有する 材料との反応生成物を含み、前記ポリアミン中の前記末端基の大半は第一級アミ ンである錯体。 2.前記オルガノボランは構造 を有し、 式中、 R1は炭素原子を1〜10個有するアルキル基であり、 R2およびR3は炭素原子を1〜10個有するアルキル基およびフェニル含 有基から互いに無関係に選択される請求項1に記載の錯体。 3.前記ジ第一級アミン末端材料は、ポリオキシアルキレンジアミン、アルキ ルジアミン、アリールジアミン、アルカリルジアミン、およびそれらの配合物か ら成る群から選択される請求項1に記載の錯体。 4.第一級アミンと反応性の基を少なくとも2個有する前記材料は、構造Y− R−Zを有し、YおよびZは第一級アミンと反応性の 部分であって且つカルボン酸、ハロゲン化カルボン酸、エステル、アルデヒド、 エポキシド、アミノアルコール、およびアクリル系誘導体から成る群から互いに 無関係に選択され、Rはニ価有機基である請求項1に記載の錯体。 5.環境条件下で自燃性でない請求項1に記載の錯体。 6.構造 を有し、 式中、 R1は炭素原子を1〜10個有するアルキル基であり、 R2およびR3は、炭素原子を1〜10個有するアルキル基およびフェニル 含有基から互いに無関係に選択され、 Amは、ジ第一級アミン末端材料と、第一級アミンと反応性の基を少なく とも2個有する材料との反応生成物を含むポリアミンであって、前記ポリアミン 中の前記末端基の大半は第一級アミンであり、 vの値は、前記錯体中の第一級アミン窒素原子とホウ素原子との有効な比 率を提供するように選択されるオルガノボランポリアミン錯体。 7.R1、R2およびR3は、炭素原子を1〜5個有するアルキル基から互いに 無関係に選択される請求項6に記載のオルガノボランポリアミン錯体。 8.R1、R2およびR3は同一である請求項7に記載のオルガノ ボランポリアミン錯体。 9.前記ポリアミンはポリオキシアルキレンジアミンである請求項6に記載の オルガノボランポリアミン錯体。 10.前記ポリオキシアルキレンジアミンは構造 H2NR4O-(R5O)w―(R6O)x―(R5O)y―R4NH2を有し、 R4、R5、およびR6は炭素原子を1〜10個有するアルキレン基であっ て、それらは同一であってもよく、あるいは異なってもよく、 wは>1であり、 xは>0であり、 yは>0である 請求項9に記載のオルガノボランポリアミン錯体。 11.R4は炭素原子を2〜4個有するアルキル基であり、R5は炭素原子を2 個または3個有するアルキル基であり、R6は炭素原子を2個または3個有する アルキル基である請求項10に記載のオルガノボランポリアミン錯体。 12.前記ポリアミンは、アルキル基が炭素原子を1〜12個有する線状アル キルジアミンである請求項6に記載のオルガノボランポリアミン錯体。 13.第一級アミンと反応性の基を少なくとも2個有する材料は構造Y−R− Zを有し、YおよびZはカルボン酸、ハロゲン化カルボン酸、エステル、アルデ ヒド、エポキシド、アミノアルコール、およびアクリル系誘導体から成る群から 互いに無関係に選択された部分であり、Rは二価有機基である請求項6に記載の オルガノボランポリアミン錯体。 14.YとZは同一であり、且つ前記錯体は実質的に線状である請求項13に 記載のオルガノボランポリアミン錯体。 15.前記錯体中の第一級アミン窒素原子とホウ素原子の比率は約0.5:1 〜4:1である請求項6に記載のオルガノボランポリアミン錯体。 16.前記錯体中の第一級アミン窒素原子とホウ素原子の比率は約1:1であ る請求項15に記載のオルガノボランポリアミン錯体。 17.アクリルモノマーの重合を開始することができるシステムであって、 a)オルガノボランおよびポリアミンを含む錯体であって、前記ポリアミ ンは、ジ第一級アミン末端材料と、第一級アミンと反応性の基を少なくとも2個 有する材料との反応生成物を含み、前記ポリアミン中の前記末端基の大半は第一 級アミンである錯体と、 b)オルガノボランを遊離させるためのアミンと反応性である化合物の有 効量と を含む前記システム。 18.前記錯体は構造 を有し、 式中、 R1は炭素原子を1〜10個有するアルキル基であり、 R2およびR3は炭素原子を1〜10個有するアルキル基およびフェニル含 有基から互いに無関係に選択され、 E-(L-E)z-L-Eはポリアミンであって、 各Eは、 (a)構造 H2NR4O-(R5O)w―(R6O)x―(R5O)y―R4NH2 を有し、式中、R4、R5およびR6は炭素原子を1〜10個有するアルキレン基 であって、それらは同一であってもよく、異なってもよく、 wは>1であり、 xは>0であり、 yは>0である ポリオキシアルキレンジアミンと、 (b)アルキル基が炭素原子を1〜12個有する線状アルキルジア ミン から成る群から選択される材料の残基であり、 各Lは、構造Y−R7−Xを有し、YおよびXはカルボン酸 、ハロゲン化カルボン酸、エステル、アルデヒド、エポキシド、アミノアルコー ル、およびアクリル系誘導体から成る群から互いに無関係に選択され、R7はニ 価有機基である材料の残基である結合基であり、 zは>0であり、 vの値は前記錯体中の第一級アミン窒素原子とホウ素原子の 有効な比率を提供するように選択される請求項16に記載のシステム。 19.R1、R2およびR3は、炭素原子を1〜5個有するアルキル基であって 且つ同一であり、 R4は、炭素原子を2〜4個有するアルキル基であり、 R5は、炭素原子を2個または3個有するアルキル基であり、 R6は、炭素原子を2個または3個有するアルキル基であり、 YおよびXは同一であって且つエポキシド、アクリル系誘導体およびカル ボン酸から成る群から選択され、 vの値は前記錯体中の第一級アミン窒素原子とホウ素原子との比率が約1:1 〜2:1であるように選択され、 前記錯体は室温で液体であり、且つ実質的に線状である、 請求項18に記載のシステム。 20.オルガノボランを遊離させるためのアミンと反応性である化合物は、イ ソシアネート、酸、酸塩化物、スルホニルクロリド、およびアルデヒドから成る 群から選択される請求項18に記載のシステム。 21.オルガノボランを遊離させるためのアミンと反応性である化合物は、ア クリル酸またはメタクリル酸である請求項20に記載のシステム。 22. a)少なくとも1種のアクリルモノマーと、 b)オルガノボランおよびポリアミンを含み、前記ポリアミンはジ 第一級アミン末端材料と、第一級アミンと反応性の基を少なくとも2個有する材 料との反応生成物を含み、前記ポリアミンの前記末端基の大半は第一級アミンで ある錯体の有効量と、 c)オルガノボランを遊離させて少なくとも1種のアクリルモノマ ーの重合を開始させるためのアミンと反応性である化合物の有効量と を含む重合可能なアクリル組成物。 23.前記少なくとも1種のアクリルモノマーは、一官能価アクリレートエス テル、一官能価メタクリレートエステル、前述のものの置換誘導体、および前述 のものの配合物から成る群から選択される請求項22に記載の重合可能なアクリ ル組成物。 24.前記一官能価メタクリレートエステルは、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 、およびそれらの配合物から成る群から選択される請求項23に記載の重合可能 なアクリル組成物。 25.前記少なくとも1種のアクリルモノマーは、メチルメタクリレートとブ チルアクリレートとの配合物を含む請求項22に記載の重合可能なアクリル組成 物。 26.エラストマー改質剤をさらに含む請求項22に記載の重合可能なアクリ ル組成物。 27.前記組成物は約0.03〜1.5重量%のホウ素を含む請求項22に記 載の重合可能なアクリル組成物。 28.前記組成物は約0.1〜0.3重量%のホウ素を含む請求項27に記載 の重合可能なアクリル組成物。 29.前記オルガノボランを遊離させるためのアミンと反応性である化合物は 、酸、イソシアネート、酸塩化物、スルホニルクロリド、およびアルデヒドから 成る群から選択される請求項22に記載の重合可能なアクリル組成物。 30. a)少なくとも1種のアクリルモノマーと、 b)構造 を有し、 式中、 R1は炭素原子を1〜10個有するアルキル基であり、 R2およびR3は炭素原子を1〜10個有するアルキル基お よびフェニル含有基から互いに無関係に選択され、 各Eは、ジ第一級アミン末端材料の残基であり、 各Lは、第一級アミンと反応性の基を少なくとも2個有する材料の残基で あり、 zは>0であり、 vの値は前記錯体中の第一級アミン原子とホウ素原子の有効な比率を提供 するように選択されるオルガノボランポリアミン錯体の有効量と、 c)オルガノボランを遊離させて少なくとも1種の有機モノマーの重合を 開始させるためのアミンと反応性である化合物の有効量と を含む重合可能なアクリル組成物。 31.各Eは、ポリオキシアルキレンジアミンの残基である、請求項30に記 載の重合可能なアクリル組成物。 32.各Eは、アルキル基が炭素原子を1〜12個有する線状アルキルジアミ ンの残基である、請求項30に記載の重合可能なアクリル組成物。 33.各Lは、構造Y−R−Xを有し、YおよびXはカルボン酸、ハロゲン化 カルボン酸、エステル、アルデヒド、エポキシド、アミノアルコール、およびア クリル系誘導体から成る群から互いに無関係に選択された部分であり、Rは二価 有機基である材料の残基である、請求項30に記載の重合可能なアクリル組成物 。 34.前記オルガノボランを遊離させるためのアミンと反応性の化合物はアク リル酸またはメタクリル酸である請求項30に記載の重合可能なアクリル組成物 。 35.第1基材と、接着剤によって第1基材に結合される第2基材とを含み、 前記接着剤は請求項30に記載の重合したアクリル組 成物を含む複合材製品。 36.第1基材はポリエチレン、ポリプロピレンおよびポリテトラフルオロエ チレンから成る群から選択される請求項37に記載の結合複合材。 37. a)アルキルアクリエートモノマーおよびアルキルメタクリレート モノマーを含むアクリルモノマーの配合物と、 b)構造 を有し、 式中、 R1、R2およびR3は炭素原子を1〜5個有するアルキル基であって、且 つ同一であり、 E-(L-E)z-L-Eはポリアミンであって、 各Eは、 (a)構造 H2NR4O-(R5O)w―(R6O)x−(R5O)y―R4NH2 を有し、式中、R4、R5およびR6は炭素原子を1〜10個有するアルキレン基 であって、それらは同一であってもよく、異なってもよく、 wは>1であり、 xは>0であり、 yは>0である ポリオキシアルキレンジアミンと、 (b)アルキル基が炭素原子を1〜12個有する線 状アルキルジアミン から成る群から選択される材料の残基であり、 各Lは、構造Y−R7−Xを有し、YおよびXは同一であり 、且つカルボン酸、ハロゲン化カルボン酸、エステル、アルデヒド、エポキシド 、アミノアルコール、およびアクリル系誘導体から成る群から選択され、R7は ニ価有機基である材料の残基である結合基であり、 zは>0であり、 vの値は前記錯体中の第一級アミン原子とホウ素原子との比 率が約1:1〜2:1であるように選択される実質的に線状のオルガノボランポ リアミン錯体と、 c)前記錯体中のオルガノボランを遊離させてアクリルモノマーの重合を 開始させるためのアクリル酸またはメタクリル酸の有効量とを含む重合可能なア クリル組成物。 38.約0.03〜1.5重量%のホウ素を含む請求項37に記載の重合可能 なアクリル組成物。 39.約0.1〜0.3重量%のホウ素を含む請求項38に記載の重合可能な アクリル組成物。 40.第1基材と、接着剤によって第1基材に結合される第2基材とを含み、 前記接着剤は請求項37に記載の重合したアクリル組成物を含み、第1基材と第 2基材は両者ともポリエチレン、ポリプロピレンおよびポリテトラフルオロエチ レンから成る群から互いに無関係に選択される複合材製品。 41.アクリルモノマーの重合を開始する方法であって、 a)少なくとも1種のアクリルモノマーを提供する工程と、 b)前記少なくとも1種のアクリルモノマーを、 i)オルガノボランおよびポリアミンを含む錯体であって、 前記ポリアミンは、ジ第一級アミン末端材料と、第一級アミンと反応性の基を少 なくとも2個有する材料との反応生成物を含み、前記ポリアミン中の前記末端基 の大半は第一級アミンである錯体と、 ii)オルガノボランを遊離させて少なくとも1種のアクリルモノマーの 重合を開始させるためのアミンと反応性である化合物の有効量と、 を含む重合開始剤系と配合する工程と、 c)少なくとも1種のアクリルモノマーの重合を開始する工程と を含む方法。 42.低表面エネルギーポリマーを基材に結合する方法であって、 a)低表面エネルギーポリマーを提供する工程と、 b)基材を提供する工程と、 c)i)少なくとも1種のアクリルモノマーと、 ii)オルガノボランおよびポリアミンをみ、前記ポリアミンは、ジ第 一級アミン末端材料と、第一級アミンと反応性の基を少なくとも2個有する材料 との反応生成物を含み、前記ポリアミン中の前記末端基の大半は第一級アミンで ある錯体の有効量と、 iii)オルガノボランを遊離させて少なくとも1種のアクリルモノマー の重合を開始させるためのアミンと反応性である化合物の有効量と、 を含む接着組成物を提供する工程と、 d)接着組成物を低表面エネルギーポリマーまたは基材のいずれかに塗付 する工程と e)低表面エネルギーポリマーと基材とをその間の接着組成 物で接続する工程と、 f)接着組成物を硬化させて低表面エネルギーポリマーと基材とを接着に より結合する工程と を含む方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/422,443 US5616796A (en) | 1995-04-14 | 1995-04-14 | Organoborane polyamine complexes and adhesive composition made therewith |
US08/422,443 | 1995-04-14 | ||
PCT/US1996/003015 WO1996032397A1 (en) | 1995-04-14 | 1996-03-06 | Organoborane polyamine complexes and adhesive compositions made therewith |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11503729A true JPH11503729A (ja) | 1999-03-30 |
JP4035634B2 JP4035634B2 (ja) | 2008-01-23 |
Family
ID=23674905
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53099996A Expired - Fee Related JP4035634B2 (ja) | 1995-04-14 | 1996-03-06 | オルガノボランポリアミン錯体およびそれを用いて作製した接着組成物 |
Country Status (10)
Country | Link |
---|---|
US (3) | US5616796A (ja) |
EP (1) | EP0820458B1 (ja) |
JP (1) | JP4035634B2 (ja) |
CN (2) | CN1056146C (ja) |
AU (1) | AU5183296A (ja) |
BR (1) | BR9604934A (ja) |
CA (1) | CA2216471A1 (ja) |
DE (1) | DE69607952T2 (ja) |
MX (1) | MX9707753A (ja) |
WO (1) | WO1996032397A1 (ja) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002527556A (ja) * | 1998-10-14 | 2002-08-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | フルオロポリマーフィルム構造体およびそれらから作製される積層品 |
JP2006522206A (ja) * | 2003-02-28 | 2006-09-28 | ダウ グローバル テクノロジーズ インコーポレイティド | シロキサン重合性成分を含むアミン有機ボラン錯体開始重合性組成物 |
JP2009538367A (ja) * | 2006-05-23 | 2009-11-05 | ダウ・コーニング・コーポレイション | アミド官能性ポリマーとのボラン触媒錯体、およびその錯体から作られる硬化性組成物 |
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 |
JP5155294B2 (ja) * | 2007-06-29 | 2013-03-06 | 株式会社トクヤマデンタル | 歯科用アルジネート印象材と印象用トレーとの接着剤およびそれを含むキット |
JP2014136706A (ja) * | 2013-01-15 | 2014-07-28 | Hitachi Chemical Co Ltd | 樹脂組成物、樹脂組成物の製造方法、樹脂組成物を含むレジスト組成物及びレジスト組成物を用いたパターン形成方法 |
WO2016002865A1 (ja) * | 2014-07-03 | 2016-01-07 | 株式会社イーテック | 2液混合型接着剤 |
Families Citing this family (80)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5690780A (en) | 1995-02-22 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
US5686544A (en) * | 1995-08-11 | 1997-11-11 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complex initiator systems and polymerizable compositions made therewith |
AU6177796A (en) * | 1995-08-11 | 1997-03-12 | Minnesota Mining And Manufacturing Company | Initiator system and adhesive composition made therewith |
WO1997017383A1 (en) * | 1995-11-07 | 1997-05-15 | Minnesota Mining And Manufacturing Company | Initiator system and adhesive composition made therewith |
US5935711A (en) * | 1996-10-23 | 1999-08-10 | 3M Innovative Properties Company | Organoborane amine complex initiator systems and polymerizable compositions made therewith |
GB9624607D0 (en) * | 1996-11-26 | 1997-01-15 | Nat Starch Chem Corp | Composition |
AU3067997A (en) * | 1997-01-17 | 1998-08-07 | Minnesota Mining And Manufacturing Company | Variable size cable closures |
US6812308B2 (en) * | 2000-11-21 | 2004-11-02 | 3M Innovative Properties Company | Initiator systems and adhesive compositions made therewith |
US6383655B1 (en) | 1998-06-12 | 2002-05-07 | 3M Innovative Properties Company | Low odor polymerizable compositions useful for bonding low surface energy substrates |
CN1132852C (zh) * | 1998-06-12 | 2003-12-31 | 美国3M公司 | 引发剂体系和由其制得的粘合剂组合物 |
US6799966B1 (en) | 1999-03-04 | 2004-10-05 | 3M Innovative Properties Company | Fluoropolymeric orthodontic article |
US6252023B1 (en) | 1999-03-19 | 2001-06-26 | 3M Innovative Properties Company | Organoborane amine complex inatator systems and polymerizable compositions made therewith |
US6565969B1 (en) | 1999-10-21 | 2003-05-20 | 3M Innovative Properties Company | Adhesive article |
US6486090B1 (en) | 1999-11-04 | 2002-11-26 | 3M Innovative Properties Company | Initiator/hydroxide and initiator/alkoxide complexes, systems comprising the complexes, and polymerized compositions made therewith |
US6410667B1 (en) * | 1999-11-04 | 2002-06-25 | 3M Innovative Properties Company | Initiator/amidine complexes, systems comprising the complexes, and polymerized compositions made therewith |
US6806330B1 (en) | 1999-12-17 | 2004-10-19 | Dow Global Technologies Inc. | Amine organoborane complex polymerization initiators and polymerizable compositions |
EP1201722A1 (en) * | 2000-10-23 | 2002-05-02 | Loctite (R & D) Limited | Polymerisation initiators, polymerisable compositions, and uses thereof |
WO2002068479A2 (en) * | 2001-02-21 | 2002-09-06 | 3M Innovative Properties Company | Polymerizable system with a long work-life |
GB0114684D0 (en) | 2001-06-15 | 2001-08-08 | Dow Chemical Co | Automobile assembly |
US20030044553A1 (en) * | 2001-08-23 | 2003-03-06 | Ravi Ramanathan | Fuel tanks |
US20030047268A1 (en) * | 2001-08-23 | 2003-03-13 | Korchnak Gregory J. | Method for repairing fuel tanks |
IE20020293A1 (en) * | 2002-04-23 | 2003-10-29 | Loctite R & D Ltd | Initiator systems, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
US6740716B2 (en) * | 2001-10-30 | 2004-05-25 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
US6849569B2 (en) | 2001-12-31 | 2005-02-01 | 3M Innovative Properties Company | Initiator systems comprising β-ketone compounds |
US6734268B2 (en) * | 2001-12-31 | 2004-05-11 | 3M Innovative Properties Company | Metal salt modifiers for bonding compositions |
US6762260B2 (en) | 2002-03-05 | 2004-07-13 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
WO2003089536A2 (en) * | 2002-04-19 | 2003-10-30 | Loctite (R & D) Limited | Polymerisation initiators based on ammonium tetraalkyl boranes, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
US6867271B1 (en) | 2002-06-24 | 2005-03-15 | Henkel Corporation | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
US7098279B2 (en) * | 2002-10-22 | 2006-08-29 | Loctite (R&D) Limited | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
BRPI0411378A (pt) * | 2003-06-09 | 2006-08-01 | Dow Global Technologies Inc | composição polimerizável de duas partes, método de polimerização, método para ligar dois ou mais componentes entre si, método para modificar a superfìcie de um polìmero de energia superficial baixa, método para revestir um substrato, composição de revestimento, laminado e composição polimerizável de uma parte |
WO2005000980A2 (en) * | 2003-06-18 | 2005-01-06 | Dow Global Technologies Inc. | Paint formulation for a low surface energy substrate |
CA2534825A1 (en) * | 2003-08-13 | 2005-02-24 | Dow Global Technologies Inc. | Method for joining piping systems and piping to equipment, fixtures, devices, structures, and appliances |
SG145726A1 (en) * | 2003-08-13 | 2008-09-29 | Dow Global Technologies Inc | Method for joining substrates and objects |
GB0326286D0 (en) | 2003-11-11 | 2003-12-17 | Vantico Gmbh | Initiator systems for polymerisable compositions |
US8501886B2 (en) * | 2003-12-22 | 2013-08-06 | Dow Global Technologies Llc | Accelerated organoborane amine complex initiated polymerizable compositions |
EP1699625B1 (en) * | 2003-12-22 | 2008-08-13 | Dow Global Technologies Inc. | Accelerated organoborane amine complex initiated polymerizable compositions |
CA2557319A1 (en) * | 2004-02-27 | 2005-09-15 | Akzo Nobel N.V. | Polymerization initiator systems containing aluminum compounds as curing inhibitors and polymerizable compositions made therewith |
US8746747B2 (en) | 2004-03-24 | 2014-06-10 | IPS Corporation—Weld-On Division | Pipe joints |
US7341285B2 (en) | 2004-03-24 | 2008-03-11 | Ips Corporation Weld-On Division | Chemical fusion of non-metallic pipe joints |
US7360552B2 (en) * | 2004-04-23 | 2008-04-22 | Dow Global Technologies Inc. | Injectable structural adhesive |
US8202932B2 (en) * | 2004-12-03 | 2012-06-19 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
CN101120026B (zh) * | 2005-02-16 | 2011-08-03 | 陶氏康宁公司 | 使用有机基硼烷胺络合物的聚合物颗粒和包封的组合物 |
US7408012B1 (en) | 2005-04-18 | 2008-08-05 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
WO2007064374A2 (en) * | 2005-08-12 | 2007-06-07 | Sugarcrm, Inc. | Customer relationship management system and method |
KR101368874B1 (ko) * | 2005-09-21 | 2014-03-04 | 다우 코닝 코포레이션 | 오가노보란 아민 착물을 사용하는 주변 조건하의리소그래피 방법 |
JP2009531468A (ja) | 2005-10-07 | 2009-09-03 | ダウ グローバル テクノロジーズ インコーポレイティド | アミド有機ボラート開始剤系 |
US7682663B2 (en) * | 2006-02-23 | 2010-03-23 | Bowling Green State University | Remote curing of polymer coating by gaseous, vaporous or aerosol initiating agent |
US20070236049A1 (en) * | 2006-03-31 | 2007-10-11 | Dow Global Technologies Inc. | Modular assembly for a vehicle |
US7524907B2 (en) * | 2006-10-12 | 2009-04-28 | Dow Global Technologies, Inc. | Accelerated organoborane initiated polymerizable compositions |
US20080103274A1 (en) * | 2006-10-12 | 2008-05-01 | Jialanella Gary L | Accelerated organoborane initiated polymerizable compositions |
EP2127631A4 (en) * | 2007-02-28 | 2011-06-29 | Tokuyama Dental Corp | ADHESIVE ADHESION ADHESION BETWEEN ALGINATE PRINT MATERIAL FOR DENTAL APPLICATIONS AND PRESSURE SHELLS, AND THIS ADHESIVE SET |
US20080299317A1 (en) * | 2007-05-29 | 2008-12-04 | Hable Christopher T | Acrylate adhesive material and method of use therefor |
US7896568B2 (en) * | 2008-03-05 | 2011-03-01 | Richard Warren Atkinson | Articulite |
US8742050B2 (en) * | 2008-03-28 | 2014-06-03 | Henkel US IP LLC | Two part hybrid adhesive |
WO2010025086A1 (en) * | 2008-08-29 | 2010-03-04 | Dow Global Technologies Inc. | Adhesive for bonding to flexible polymer surfaces |
CN102197039A (zh) | 2008-10-23 | 2011-09-21 | 陶氏环球技术有限责任公司 | 用于有机硼烷化合物的封闭剂 |
US8871341B2 (en) | 2010-11-01 | 2014-10-28 | Dow Global Technologies Llc | Polyolefins having one or more surfaces modified to improve adhesion of polyisocyanate functional adhesives thereto |
GB2491170B (en) | 2011-05-26 | 2013-11-06 | Henkel Ireland Ltd | Two-part polymerisable compositions |
CN102838085B (zh) * | 2012-09-18 | 2014-04-02 | 武汉凯迪工程技术研究总院有限公司 | 一种高容量高分子聚合物储氢材料及其制备方法 |
US9382452B2 (en) | 2013-02-07 | 2016-07-05 | Illinois Tool Works, Inc. | Low surface energy bonding adhesive formulation and process for the use thereof |
KR102335364B1 (ko) | 2014-03-27 | 2021-12-06 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 오가노보란-함유 조성물, 및 그의 사용 방법 |
JP6258563B1 (ja) | 2014-11-14 | 2018-01-10 | スリーエム イノベイティブ プロパティズ カンパニー | 2液型接着剤組成物及び接着剤組成物の製造方法 |
US10889687B2 (en) | 2015-09-10 | 2021-01-12 | 3M Innovative Properties Company | Polymerizable compositions, polymerized compositions, and methods of making and using the same |
JP6190933B2 (ja) | 2016-02-09 | 2017-08-30 | サンメディカル株式会社 | 重合性組成物およびキット、ならびに重合開始剤 |
EP3415539B1 (en) | 2016-02-09 | 2022-03-30 | Sun Medical Co., Ltd. | Polymerizable composition and kit thereof, and polymerization initiator |
EP3464495A4 (en) | 2016-05-27 | 2020-03-04 | IPS Corporation | POLYMER-POLY (METH) ACRYLATE INTERPENETRATIVE POLYMER NETWORK ADHESIVE COMPOSITIONS AND METHOD OF USING THE SAME |
CN106497440A (zh) * | 2016-11-11 | 2017-03-15 | 台州吉谷胶业股份有限公司 | 一种环保型常温固化双组分聚烯烃胶粘剂 |
EP3556804A4 (en) | 2016-12-16 | 2019-11-13 | Denka Company Limited | COMPOSITION |
CN111094398B (zh) | 2017-09-26 | 2023-02-14 | 3M创新有限公司 | 可固化的密封剂组合物、密封帽以及它们的制备和使用方法 |
EP3689945A4 (en) * | 2017-09-29 | 2021-06-02 | Sun Medical Co., Ltd. | COMPOSITE PARTICLES, KIT, MATERIAL AND PROCESS FOR THE PRODUCTION OF COMPOSITE PARTICLES |
US11866609B2 (en) | 2017-12-13 | 2024-01-09 | 3M Innovative Properties Company | Optically clear adhesives containing a trialkyl borane complex initiator and photoacid |
WO2019239273A1 (en) | 2018-06-15 | 2019-12-19 | 3M Innovative Properties Company | Assemblies and methods of making a shim |
US10995240B2 (en) * | 2018-07-20 | 2021-05-04 | Palo Alto Research Center Incorporated | All-in-one fast curing acrylic structural adhesive |
EP3856849A1 (en) | 2018-09-27 | 2021-08-04 | 3M Innovative Properties Company | Composition including amino-functional silanes and method of applying a sealant to a substrate |
CN112969742A (zh) | 2018-11-09 | 2021-06-15 | 3M创新有限公司 | 可固化密封剂组合物、密封帽以及它们的制备和使用方法 |
GB2580162B (en) | 2018-12-21 | 2022-07-13 | Henkel IP & Holding GmbH | One-part photocurable (meth) acrylate compositions |
WO2020202076A1 (en) | 2019-04-04 | 2020-10-08 | 3M Innovative Properties Company | Method of irradiating a composition through a substrate |
EP4003708A1 (en) | 2019-07-25 | 2022-06-01 | 3M Innovative Properties Company | Methods of shimming an assembly |
WO2022254369A1 (en) | 2021-06-02 | 2022-12-08 | 3M Innovative Properties Company | Composition including cyclic imide-containing monomer and organoborane complex and related articles and methods |
CN113736424A (zh) * | 2021-09-30 | 2021-12-03 | 烟台德邦科技股份有限公司 | 一种单组分热固性聚氨酯结构胶及其制备方法 |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2985633A (en) * | 1958-10-30 | 1961-05-23 | Union Carbide Corp | Polymerization of ethylene with organoboron compounds treated with oxygen |
US3340193A (en) * | 1960-12-30 | 1967-09-05 | Monsanto Co | Mineral oil containing alkyl polymethacrylate antifoamant |
US3275611A (en) * | 1960-12-30 | 1966-09-27 | Monsanto Co | Process for polymerizing unsaturated monomers with a catalyst comprising an organoboron compound, a peroxygen compound and an amine |
US3141862A (en) * | 1961-03-01 | 1964-07-21 | Exxon Research Engineering Co | Graft copolymerization using boron alkyls in the presence of oxygen as catalysts |
BE602558A (ja) * | 1961-03-14 | |||
US3257360A (en) * | 1961-07-27 | 1966-06-21 | Monsanto Co | Terpolymers and processes for making same |
US3306809A (en) * | 1961-08-21 | 1967-02-28 | Union Carbide Corp | Curable polyepoxide and glycol polyamine compositions |
GB1113722A (en) * | 1964-05-21 | 1968-05-15 | Minnesota Mining & Mfg | Aerobically polymerisable compositions |
BE674405A (ja) * | 1965-01-06 | 1966-06-28 | ||
US3425988A (en) * | 1965-01-27 | 1969-02-04 | Loctite Corp | Polyurethane polyacrylate sealant compositions |
BE524840A (ja) * | 1965-12-17 | |||
US3418260A (en) * | 1966-01-20 | 1968-12-24 | Du Pont | Imidazole-borane polymers |
US3527737A (en) * | 1967-09-15 | 1970-09-08 | G C Kagaku Kogyo Kk | Adhesive compositions |
JPS4616888Y1 (ja) * | 1968-02-15 | 1971-06-12 | ||
JPS4818928B1 (ja) * | 1969-12-13 | 1973-06-09 | ||
JPS5137092B2 (ja) * | 1972-04-28 | 1976-10-13 | ||
JPS53102394A (en) * | 1977-02-18 | 1978-09-06 | Hitachi Ltd | Two-pack type resin composition |
US4167616A (en) * | 1977-08-22 | 1979-09-11 | Rohm And Haas Company | Polymerization with diborane adducts or oligomers of boron-containing monomers |
US4507342A (en) * | 1979-05-08 | 1985-03-26 | Rohm And Haas Company | Polymers adherent to polyolefins |
DE3207263A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Organo-borverbindungen enthaltende stoffgemische, verfahren zu ihrer herstellung und ihre verwendung |
DE3201780A1 (de) * | 1982-01-21 | 1983-08-25 | Henkel KGaA, 4000 Düsseldorf | Neue polymere organo-borverbindungen und ihre verwendung |
DE3201731A1 (de) * | 1982-01-21 | 1983-07-28 | Henkel KGaA, 4000 Düsseldorf | "aerob haertende kunststoffmassen" |
US4379728A (en) * | 1982-02-04 | 1983-04-12 | W. R. Grace & Co. | Cyanourea compounds or polymers thereof as epoxy resin curing agents |
DE3207264A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Neue boralkylverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
US4524181A (en) * | 1983-08-11 | 1985-06-18 | Minnesota Mining And Manufacturing Company | Curable epoxy compositions and cured resins obtained therefrom |
US4485229A (en) * | 1984-02-15 | 1984-11-27 | Texaco Inc. | Epoxy resin containing a combination of high and low molecular weight polyoxyalkylene polyamine curing agents |
DE3518965A1 (de) * | 1985-05-25 | 1986-11-27 | Henkel KGaA, 40589 Düsseldorf | Schmelzbare und dabei aerob aushaertende kunststoffmassen und verfahren zu ihrer herstellung |
US4874814A (en) * | 1985-07-02 | 1989-10-17 | Monsanto Company | Cross-linked polyvinyl butyral |
JP2528098B2 (ja) * | 1986-06-06 | 1996-08-28 | 三井石油化学工業株式会社 | セラミックス用接着剤 |
US4904360A (en) * | 1986-09-12 | 1990-02-27 | Minnesota Mining And Manufacturing Company | Water-compatible coating composition |
CA1292591C (en) * | 1986-10-30 | 1991-11-26 | Takeshi Sakashita | Curable composition |
JPH075680B2 (ja) * | 1987-07-03 | 1995-01-25 | 三井石油化学工業株式会社 | 硬化性組成物 |
JP2811839B2 (ja) * | 1989-12-06 | 1998-10-15 | 三井化学株式会社 | 歯科用チタンまたはその合金用硬化性接着剤組成物 |
JP2812527B2 (ja) * | 1990-03-15 | 1998-10-22 | 三井化学株式会社 | 歯科接着剤用触媒ペースト状組成物 |
US5106928A (en) * | 1991-04-29 | 1992-04-21 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
US5143884A (en) * | 1991-04-29 | 1992-09-01 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
JPH05235089A (ja) * | 1992-02-26 | 1993-09-10 | Fujitsu Ltd | フェイスダウン実装用半導体チップ |
US5286821A (en) * | 1992-03-17 | 1994-02-15 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
US5401805A (en) * | 1992-04-06 | 1995-03-28 | The Penn State Research Foundation | Olefin graft copolymers prepared using borane-containing olefin backbone polymers |
US5310835A (en) * | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
CN1054136C (zh) * | 1994-02-22 | 2000-07-05 | 美国3M公司 | 可聚合的丙烯酸组合物和将两个基材粘合在一起的方法 |
-
1995
- 1995-04-14 US US08/422,443 patent/US5616796A/en not_active Expired - Lifetime
-
1996
- 1996-03-06 AU AU51832/96A patent/AU5183296A/en not_active Abandoned
- 1996-03-06 DE DE69607952T patent/DE69607952T2/de not_active Expired - Fee Related
- 1996-03-06 EP EP96908666A patent/EP0820458B1/en not_active Expired - Lifetime
- 1996-03-06 JP JP53099996A patent/JP4035634B2/ja not_active Expired - Fee Related
- 1996-03-06 MX MX9707753A patent/MX9707753A/es unknown
- 1996-03-06 WO PCT/US1996/003015 patent/WO1996032397A1/en active IP Right Grant
- 1996-03-06 CN CN96193252A patent/CN1056146C/zh not_active Expired - Fee Related
- 1996-03-06 CA CA002216471A patent/CA2216471A1/en not_active Abandoned
- 1996-03-06 BR BR9604934A patent/BR9604934A/pt not_active IP Right Cessation
- 1996-12-16 US US08/766,073 patent/US5684102A/en not_active Expired - Fee Related
- 1996-12-16 US US08/767,578 patent/US5795657A/en not_active Expired - Fee Related
-
1999
- 1999-11-24 CN CNB991209672A patent/CN1170673C/zh not_active Expired - Fee Related
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002527556A (ja) * | 1998-10-14 | 2002-08-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | フルオロポリマーフィルム構造体およびそれらから作製される積層品 |
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 |
JP2006522206A (ja) * | 2003-02-28 | 2006-09-28 | ダウ グローバル テクノロジーズ インコーポレイティド | シロキサン重合性成分を含むアミン有機ボラン錯体開始重合性組成物 |
JP2009538367A (ja) * | 2006-05-23 | 2009-11-05 | ダウ・コーニング・コーポレイション | アミド官能性ポリマーとのボラン触媒錯体、およびその錯体から作られる硬化性組成物 |
JP5155294B2 (ja) * | 2007-06-29 | 2013-03-06 | 株式会社トクヤマデンタル | 歯科用アルジネート印象材と印象用トレーとの接着剤およびそれを含むキット |
JP2014136706A (ja) * | 2013-01-15 | 2014-07-28 | Hitachi Chemical Co Ltd | 樹脂組成物、樹脂組成物の製造方法、樹脂組成物を含むレジスト組成物及びレジスト組成物を用いたパターン形成方法 |
WO2016002865A1 (ja) * | 2014-07-03 | 2016-01-07 | 株式会社イーテック | 2液混合型接着剤 |
Also Published As
Publication number | Publication date |
---|---|
DE69607952T2 (de) | 2000-12-07 |
CN1056146C (zh) | 2000-09-06 |
CA2216471A1 (en) | 1996-10-17 |
US5795657A (en) | 1998-08-18 |
CN1259430A (zh) | 2000-07-12 |
MX9707753A (es) | 1997-11-29 |
DE69607952D1 (de) | 2000-05-31 |
US5684102A (en) | 1997-11-04 |
CN1181085A (zh) | 1998-05-06 |
EP0820458B1 (en) | 2000-04-26 |
BR9604934A (pt) | 1998-06-09 |
CN1170673C (zh) | 2004-10-13 |
JP4035634B2 (ja) | 2008-01-23 |
AU5183296A (en) | 1996-10-30 |
US5616796A (en) | 1997-04-01 |
EP0820458A1 (en) | 1998-01-28 |
WO1996032397A1 (en) | 1996-10-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH11503729A (ja) | オルガノボランポリアミン錯体およびそれを用いて作製した接着組成物 | |
JP3928072B2 (ja) | 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 | |
EP1179024B1 (en) | Organoborane amine complex initiator systems and polymerizable compositions made therewith | |
US5935711A (en) | Organoborane amine complex initiator systems and polymerizable compositions made therewith | |
JP3535167B2 (ja) | 有機ホウ素アミン錯体に基づく重合開始剤システムを用いて製造される重合性組成物 | |
JP4855617B2 (ja) | 開始剤/ヒドロキシド錯体および開始剤/アルコキシド錯体、その錯体を含む系、ならびにそれを用いて製造される重合組成物 | |
JP4373007B2 (ja) | 低表面エネルギー基材の接着用に有用な低臭気重合性組成物 | |
JP2003517009A (ja) | アミンオルガノボラン錯体重合開始剤および重合性組成物 | |
EP1263907B1 (en) | Polymerization initiator systems and bonding compositions comprising vinyl aromatic compounds | |
KR20080053348A (ko) | 아미도-유기보레이트 개시제 시스템 | |
JP4975952B2 (ja) | Ss−ケトン化合物を含む開始剤系および該開始剤系により製造された接着用組成物 | |
JP2004149808A (ja) | 2つの基材を接着する方法 | |
MXPA97007865A (en) | Complexes of organoganorous polioxyqualen polypoliamins and adhesive compositions made with the mis |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060905 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20060828 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20061205 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20070129 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070301 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20070301 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070424 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20070911 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20071011 |
|
A72 | Notification of change in name of applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A721 Effective date: 20071011 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101109 Year of fee payment: 3 |
|
LAPS | Cancellation because of no payment of annual fees |