JPH11510845A - オルガノボランポリアミン錯体開始剤系および同剤を用いて製造される重合可能な組成物 - Google Patents
オルガノボランポリアミン錯体開始剤系および同剤を用いて製造される重合可能な組成物Info
- Publication number
- JPH11510845A JPH11510845A JP9509265A JP50926597A JPH11510845A JP H11510845 A JPH11510845 A JP H11510845A JP 9509265 A JP9509265 A JP 9509265A JP 50926597 A JP50926597 A JP 50926597A JP H11510845 A JPH11510845 A JP H11510845A
- Authority
- JP
- Japan
- Prior art keywords
- polyol
- polyamine
- group
- organoborane
- polymerizable
- 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 304
- 229920000768 polyamine Polymers 0.000 title claims abstract description 142
- 239000003999 initiator Substances 0.000 title description 10
- 229920005862 polyol Polymers 0.000 claims abstract description 137
- 150000003077 polyols Chemical class 0.000 claims abstract description 135
- 239000000178 monomer Substances 0.000 claims abstract description 123
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 105
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 67
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 67
- 239000004814 polyurethane Substances 0.000 claims abstract description 61
- 229920002396 Polyurea Polymers 0.000 claims abstract description 43
- 229920003226 polyurethane urea Polymers 0.000 claims abstract description 37
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 36
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 11
- 239000000853 adhesive Substances 0.000 claims description 167
- 230000001070 adhesive effect Effects 0.000 claims description 167
- -1 polytetramethylene Polymers 0.000 claims description 69
- 239000000463 material Substances 0.000 claims description 52
- 239000000126 substance Substances 0.000 claims description 51
- 239000007788 liquid Substances 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 43
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 40
- 239000000758 substrate Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 229910052796 boron Inorganic materials 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 229920001451 polypropylene glycol Polymers 0.000 claims description 17
- 239000004698 Polyethylene Substances 0.000 claims description 16
- 229920000573 polyethylene Polymers 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 125000005442 diisocyanate group Chemical group 0.000 claims description 14
- 238000003860 storage Methods 0.000 claims description 14
- 239000002562 thickening agent Substances 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 13
- 229920000570 polyether Polymers 0.000 claims description 13
- 239000004743 Polypropylene Substances 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 229920005906 polyester polyol Polymers 0.000 claims description 12
- 229920001155 polypropylene Polymers 0.000 claims description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 9
- 229920001610 polycaprolactone Polymers 0.000 claims description 9
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- 239000006193 liquid solution Substances 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 3
- 230000000977 initiatory effect Effects 0.000 claims 3
- 229920000642 polymer Polymers 0.000 abstract description 40
- 239000003522 acrylic cement Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 description 32
- 229920002635 polyurethane Polymers 0.000 description 24
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 20
- 239000004926 polymethyl methacrylate Substances 0.000 description 19
- 150000003141 primary amines Chemical class 0.000 description 19
- 239000004848 polyfunctional curative Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920003023 plastic Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- 125000004386 diacrylate group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 8
- 239000012790 adhesive layer Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 229910000085 borane Inorganic materials 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 239000003292 glue Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- 239000004971 Cross linker Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000011258 core-shell material Substances 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
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- 229920001281 polyalkylene Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-UHFFFAOYSA-N 0.000 description 2
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- 239000004970 Chain extender Substances 0.000 description 2
- 102100026735 Coagulation factor VIII Human genes 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 2
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- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
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- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 2
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- 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
- WMPJPAMWRAOQSU-UHFFFAOYSA-N naphthalene-1,2-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(C=O)=CC=C21 WMPJPAMWRAOQSU-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 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
- 239000005022 packaging material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 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
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 150000003335 secondary amines Chemical group 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- DCVWZWOEQMSMLR-UHFFFAOYSA-N silylperoxysilane Chemical compound [SiH3]OO[SiH3] DCVWZWOEQMSMLR-UHFFFAOYSA-N 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 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
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 229920001897 terpolymer Polymers 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
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011023 white opal Substances 0.000 description 1
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.オルガノボランポリアミン錯体およびポリオールを含む組成物。 2.前記オルガノボランポリアミン錯体と前記ポリオールの室温で液体の溶液 である請求項1に記載の組成物。 3.前記ポリオールはヒドロキシル官能価が2〜3である請求項1に記載の組 成物。 4.前記ポリオールはポリエーテルポリオールとポリエステルポリオールから 成る群から選択される請求項1に記載の組成物。 5.前記ポリオールはポリアルキレンオキシドポリオールである請求項4に記 載の組成物。 6.前記ポリオールはポリエチレンオキシドポリオール、ポリプロピレンオキ シドポリオール、ポリテトラメチレンオキシドポリオール、これらの物質のエチ レンオキシド末端誘導体およびプロピレンオキシド末端誘導体、ポリ-ε-カプロ ラクトンポリオール、および前述の物質の配合物から成る群から選択される請求 項4に記載の組成物。 7.(a)(1)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オルガノボランと、 (2)アルキルポリアミン、ポリオキシアルキレンポリアミン、お よびジ第一級アミン末端物質と第一級アミンと反応性の基を少なくとも2個有す る物質との反応生成物から成る群から選択されたポリアミンであって、反応混合 物中の第一級アミン基の数は第一級アミンと反応性の基の数より多いポリアミン と の錯体と (b)ポリエチレンオキシドポリオール、ポリプロピレンオキシドポリオ ール、ポリテトラメチレンオキシドポリオール、これらの物質のエチレンオキシ ド末端誘導体およびプロピレンオキシド末端誘導体、ポリ-ε-カプロラクトン、 および前述の物質の配合物から成る群から選択されたポリオールと を含む室温で液体の溶液。 8.(a)オルガノボランポリアミン錯体と、 (b)オルガノボランを遊離させるための前記錯体のポリアミン成分と反 応性のポリイソシアネートと、 (c)ポリオールと を含む重合開始剤系。 9.前記ポリオールはポリエーテルポリオールおよびポリエステルポリオール から成る群から選択される請求項8に記載の重合開始剤系。 10.前記ポリイソシアネートはアクリルモノマーに溶解できる 請求項8に記載の重合開始剤系。 11.イソシアネート官能価の当量数は、アミン官能価の当量数とヒドロキシ ル官能価の当量数の和に等しい請求項8に記載の重合開始剤系。 12.室温でアクリルモノマーの重合開始とポリウレタン/ポリウレアの形成 の両者が可能な系であって、 (a)オルガノボランポリアミン錯体とポリオールの溶液であって、前記 ポリオールは前記ポリアミンと反応性でない溶液と、 (b)前記アクリルモノマーの重合を開始するために前記オルガノボラン を遊離させるための前記ポリアミンと反応性であるジイソシアネートであって、 前記アクリルモノマーに溶解でき、且つ前記ポリウレタン/ポリウレアを形成す るための前記ポリアミンと前記ポリオールの両者と反応性である前記ジイソシア ネートと、 を含む前記系。 13.前記ポリオールは、ポリエチレンオキシドポリオール、ポリプロピレン オキシドポリオール、ポリテトラメチレンオキシドポリオール、これらの物質の エチレンオキシド末端誘導体およびプロピレンオキシド末端誘導体、ポリ-ε-カ プロラクトン、および前述の物質の配合物から成る群から選択される請求項12 に記載の系。 14.イソシアネート官能価の当量数は、アミン官能価の当量数とヒドロキシ ル官能価の当量数の和に等しい請求項12に記載の系。 15.(a)重合可能なアクリルモノマーと、 (b)オルガノボランポリアミン錯体と、 (c)ポリオールと、 (d)ポリイソシアネートと、 (e)任意に、有機増粘剤と を含む重合可能な組成物。 16.前記重合可能な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、前述の物質の置換誘導体、および前述の物質 の配合物から成る群から選択される請求項15に記載の重合可能な組成物。 17.前記組成物は、重合可能な組成物中のアクリル基含有成分および任意の 有機増粘剤の重量を基準にして約0.03〜1.5重量%のホウ素を含む請求項 15に記載の重合可能な組成物。 18.前記組成物は、重合可能な組成物中のアクリル基含有成分および任意の 有機増粘剤の重量を基準にして約0.1〜0.3重量%のホウ素を含む請求項17 に記載の重合可能な組成物。 19.前記オルガノボランポリアミン錯体は構造 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、 Amはアルキルポリアミン、ポリオキシアルキレンポリアミン、およびジ 第一級アミン末端物質と第一級アミンと反応性の基を少なくとも2個有する物質 との反応生成物から成る群から選択されるポリアミンであって、反応混合物中の 第一級アミン基の数は第一 級アミンと反応性の基より多く、 vの値は錯体中の第一級アミン窒素原子とホウ素原子の有効比を提供する ように選択される 請求項15に記載の重合可能な組成物。 20.前記ポリオールはポリエーテルポリオールおよびポリエステルポリオー ルから成る群から選択される請求項15に記載の重合可能な組成物。 21.前記ポリオールはポリアルキレンオキシドポリオールである請求項20 に記載の重合可能な組成物。 22.前記ポリオールは、ポリエチレンオキシドポリオール、ポリプロピレン オキシドポリオール、ポリテトラメチレンオキシドポリオール、これらの物質の エチレンオキシド末端誘導体およびプロピレンオキシド末端誘導体、ポリ-ε-カ プロラクトン、および前述の物質の配合物から成る群から選択される請求項20 に記載の重合可能な組成物。 23.前記ポリイソシアネートはジイソシアネートである請求項15に記載の 重合可能な組成物。 24.前記オルガノボランポリアミン錯体は前記ポリオールに溶解でき、前記 ポリオールは前記アクリルモノマーに溶解できる請求項15に記載の重合可能な 組成物。 25.前記ポリイソシアネートは前記アクリルモノマーに溶解できる請求項2 4に記載の重合可能な組成物。 26.遊離基重合可能基とアミンと反応性の基の両者を有する化合物か、ポリ イソシアネートと反応して遊離基重合可能基とアミンと反応性の基の両者を有す る化合物を形成する物質のいずれかをさ らに含む請求項15に記載の重合可能な組成物。 27.ヒドロキシル化(メト)アクリレートをさらに含む請求項15に記載の 重合可能な組成物。 28.ポリウレタン形成触媒をさらに含む請求項15に記載の重合可能な組成 物。 29.室温で適用して硬化させることができる接着剤組成物であって、 (a)アルキルアクリレートモノマーとアルキルメタクリレートモノマー の重合可能な配合物と、 (b)任意の有機増粘剤と、 (c)接着剤組成物中のアクリル基含有物質および任意の有機増粘剤の重 量を基準にして約0.08〜0.5重量%のホウ素を提供するオルガノボランポ リアミン錯体であって、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はアルキルポリアミン、ポリオキシアルキレンポリアミン、およびジ 第一級アミン末端物質と第一級アミンと反応性の基を少なくとも2個有する物質 との反応生成物から成る群から選択されるポリアミンであって、反応混合物中の 第一級アミン基の数は第一 級アミンと反応性の基より多く、 vの値は錯体中の第一級アミン窒素原子とホウ素原子の有効比を提供する ように選択されるオルガノボランポリアミン錯体と、 (d)前記オルガノボランポリアミン錯体が溶解でき、且つポリエチレン オキシドポリオール、ポリプロピレンオキシドポリオール、ポリテトラメチレン オキシドポリオール、これらの物質のエチレンオキシド末端誘導体およびプロピ レンオキシド末端誘導体、ポリ-ε-カプロラクトンポリオール、および前述の物 質の配合物から成る群から選択されるポリオールと、 (e)前記ポリアミンと反応して前記重合可能な配合物の重合を開始する ためのオルガノボランを遊離させ、前記ポリアミンおよび前記ポリオールと反応 してポリウレタン/ポリウレアを形成する有効量のジイソシアネートと を含む接着剤組成物。 30.100%固形分の、2液型硬化性接着剤組成物であって、 (a)オルガノボランポリアミン錯体とポリオールの溶液を含み、前記ポ リオールは前記ポリアミンと反応性でない第1液と、 (b)(1)重合可能なアクリルモノマーと、 (2)前記アクリルモノマーに溶解するポリイソシアネートであっ て、ポリアミンと反応して前記アクリルモノマーの重合を開始するためのオルガ ノボランを遊離させ、且つ前記ポリオールおよび前記ポリアミンと反応してポリ ウレタン/ポリウレアを形成するのに十分な量で提供される前記ポリイソシアネ ートと (3)ポリウレタン形成触媒と、 (4)任意に、遊離基重合可能基とアミンと反応性の 基の両者を有する化合物か、ポリイソシアネートと反応して遊離基重合可能基と アミンと反応性の基の両者を有する化合物を形成する物質のいずれかと を含む第2液と を含む2液型硬化性接着剤組成物。 31.前記ポリオールはポリエチレンオキシドポリオール、ポリプロピレンオ キシドポリオール、ポリテトラメチレンオキシドポリオール、これらの物質のエ チレンオキシド末端誘導体およびプロピレンオキシド末端誘導体、ポリ-ε-カプ ロラクトン、および前述の物質の配合物から成る群から選択される請求項30に 記載の100%固形分の、2液型硬化性接着剤組成物。 32.前記第1液と前記第2液は1:1〜1:10の自然数比で配合される請 求項30に記載の100%固形分の、2液型硬化性接着剤組成物。 33.前記第1液と前記第2液は各々2液型接着剤ディスペンサーの異なる容 器内にある請求項30に記載の100%固形分の、2液型硬化性接着剤組成物。 34.(a)重合したアクリル系誘導体と、 (b)前記重合したアクリル系誘導体と独立したポリウレタン/ポリウ レアと、 (c)オルガノボランおよび/またはオルガノボラン分解副生成物と を含む硬化した接着剤組成物。 35.重合したアクリル系誘導体と前記ポリウレタン/ポリウレアを結合する 化合物をさらに含む請求項34に記載の硬化した接着 剤組成物。 36.前記ポリウレタン/ポリウレアは室温より高いガラス転移温度を有する 請求項34に記載の硬化した接着剤組成物。 37.請求項34に記載の硬化した接着剤組成物の層によって接着された第1 基材と第2基材を含む結合された複合材。 38.前記第1基材と前記第2基材は低表面エネルギー高分子材料から各々無 関係に選択される請求項37に記載の結合された複合材。 39.前記第1基材と前記第2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各々無関係に選択される請求項38に 記載の結合された複合材。 40.重合可能なアクリルモノマー、オルガノボランポリアミン錯体、および オルガノボランを遊離させるためのポリアミンと反応して前記アクリルモノマー の重合を開始する物質を含む2液型重合可能接着剤組成物の貯蔵安定性を改良す る方法であって、 (a)オルガノボランポリアミン錯体を提供する工程と、 (b)オルガノボランポリアミン錯体が溶解できるポリオールを提供する 工程と、 (c)前記ポリオールと前記オルガノボランポリアミン錯体の溶液を形成 する工程と、 (d)第1液は(i)前記ポリアミンと反応する物質と(ii)前記重合可 能なアクリルモノマー全部を含み、第2液は前記ポリオールと前記オルガノボラ ンポリアミン錯体の溶液を含む、2液型重合可能接着剤組成物を調製する工程と を含む方法。 41.重合可能なアクリルモノマー、オルガノボランポリアミン錯体、および オルガノボランを遊離させるためのポリアミンと反応して前記アクリルモノマー の重合を開始する物質を含む2液型重合可能接着剤組成物において、前記重合し た接着剤組成物中で移動することができる物質の量を減少させる方法であって、 前記物質は前記ポリアミンと、ポリアミンと反応する物質との反応生成物を含み 、 (a)前記錯体の前記ポリアミン成分と反応性であるポリイソシアネート を提供する工程と、 (b)前記ポリイソシアネートと反応性であるポリオールを提供する工程 と、 (c)ポリイソシアネートを前記ポリアミンと反応させて前記オルガノボ ランを遊離させる工程と、 (d)前記遊離したオルガノボランでアクリルモノマーの重合を開始し、 前記アクリルモノマーを重合してアクリルポリマーを形成する工程と、 (e)ポリアミン、ポリイソシアネートおよびポリオールを反応させて、 アクリルポリマーと独立しているがアクリルポリマーと共存するポリウレタン/ ポリウレアを形成させる工程と を含む方法。 42.イソシアネート官能価の当量数は、アミン官能価の当量数とヒドロキシ ル官能価の当量数の和に等しい請求項41に記載の方法。
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PCT/US1996/011190 WO1997007151A1 (en) | 1995-08-11 | 1996-07-01 | Organoborane polyamine complex initiator systems and polymerizable compositions made therewith |
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1995
- 1995-08-11 US US08/514,190 patent/US5686544A/en not_active Expired - Lifetime
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1996
- 1996-07-01 DE DE69613378T patent/DE69613378T2/de not_active Expired - Lifetime
- 1996-07-01 CN CN96196202A patent/CN1100806C/zh not_active Expired - Fee Related
- 1996-07-01 WO PCT/US1996/011190 patent/WO1997007151A1/en active IP Right Grant
- 1996-07-01 BR BR9609933A patent/BR9609933A/pt not_active IP Right Cessation
- 1996-07-01 EP EP96924339A patent/EP0843695B1/en not_active Expired - Lifetime
- 1996-07-01 JP JP50926597A patent/JP4134302B2/ja not_active Expired - Fee Related
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1997
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Cited By (7)
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 |
JP2005507969A (ja) * | 2001-10-30 | 2005-03-24 | ダウ グローバル テクノロジーズ インコーポレイティド | 有機ボラン・アミン錯体重合開始剤および重合性組成物 |
JP2010280891A (ja) * | 2001-10-30 | 2010-12-16 | Dow Global Technologies Inc | 有機ボラン・アミン錯体重合開始剤および重合性組成物 |
JP2009541531A (ja) * | 2006-06-20 | 2009-11-26 | ダウ・コーニング・コーポレーシヨン | 硬化可能な有機ケイ素組成物 |
JP2011515565A (ja) * | 2008-03-28 | 2011-05-19 | ヘンケル コーポレイション | 2パート・ハイブリッド接着剤 |
JP2020533433A (ja) * | 2017-08-31 | 2020-11-19 | ハーキュリーズ エルエルシー | ウレタンアクリレートハイブリッド構造接着剤 |
WO2020110911A1 (ja) * | 2018-11-27 | 2020-06-04 | 株式会社イーテック | 2液混合型接着剤 |
Also Published As
Publication number | Publication date |
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DE69613378T2 (de) | 2002-05-02 |
AU6482296A (en) | 1997-03-12 |
MX9800917A (es) | 1998-05-31 |
EP0843695A1 (en) | 1998-05-27 |
BR9609933A (pt) | 1999-06-08 |
CN1192756A (zh) | 1998-09-09 |
DE69613378D1 (de) | 2001-07-19 |
EP0843695B1 (en) | 2001-06-13 |
US5994484A (en) | 1999-11-30 |
CN1100806C (zh) | 2003-02-05 |
JP4134302B2 (ja) | 2008-08-20 |
CA2229166A1 (en) | 1997-02-27 |
US6008308A (en) | 1999-12-28 |
US5686544A (en) | 1997-11-11 |
US6093778A (en) | 2000-07-25 |
WO1997007151A1 (en) | 1997-02-27 |
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