JP2021528524A - プライマーレスポリウレタン接着剤組成物 - Google Patents
プライマーレスポリウレタン接着剤組成物 Download PDFInfo
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- JP2021528524A JP2021528524A JP2020569116A JP2020569116A JP2021528524A JP 2021528524 A JP2021528524 A JP 2021528524A JP 2020569116 A JP2020569116 A JP 2020569116A JP 2020569116 A JP2020569116 A JP 2020569116A JP 2021528524 A JP2021528524 A JP 2021528524A
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- adhesive composition
- polyurethane adhesive
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- 239000000203 mixture Substances 0.000 title claims abstract description 194
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 159
- 239000000853 adhesive Substances 0.000 title claims abstract description 158
- 239000004814 polyurethane Substances 0.000 title claims abstract description 139
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 139
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 31
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910000077 silane Inorganic materials 0.000 claims abstract description 21
- 239000000945 filler Substances 0.000 claims abstract description 19
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims description 35
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 33
- 239000012948 isocyanate Substances 0.000 claims description 30
- -1 aromatic isocyanates Chemical class 0.000 claims description 27
- 239000006229 carbon black Substances 0.000 claims description 25
- 235000019241 carbon black Nutrition 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000011521 glass Substances 0.000 claims description 24
- 229920005862 polyol Polymers 0.000 claims description 19
- 150000003077 polyols Chemical class 0.000 claims description 19
- 235000010216 calcium carbonate Nutrition 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 229920003023 plastic Polymers 0.000 claims description 12
- 239000004033 plastic Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 8
- 238000010586 diagram Methods 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 description 21
- 239000005056 polyisocyanate Substances 0.000 description 21
- 229920001228 polyisocyanate Polymers 0.000 description 21
- 229920000768 polyamine Polymers 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 239000004014 plasticizer Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 229910000019 calcium carbonate Inorganic materials 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000557626 Corvus corax Species 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 101150072074 UL28 gene Proteins 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 3
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- 238000000518 rheometry Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229940116351 sebacate Drugs 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical class [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- 101150046896 trm1 gene Proteins 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical class O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
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- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
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- 229910052582 BN Inorganic materials 0.000 description 1
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- 229910001369 Brass Inorganic materials 0.000 description 1
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- 239000009261 D 400 Substances 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
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- WMTLVUCMBWBYSO-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 Chemical class N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 WMTLVUCMBWBYSO-UHFFFAOYSA-N 0.000 description 1
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- 239000004696 Poly ether ether ketone Substances 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/2018—Heterocyclic amines; Salts thereof containing one heterocyclic ring having one nitrogen atom in the ring
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/4825—Polyethers containing two hydroxy groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
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- C08K3/26—Carbonates; Bicarbonates
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Abstract
【選択図】なし
Description
(a)イソシアネート部位を有する1種以上のウレタンプレポリマーと、
(b)触媒量の1種以上の触媒と、
(c)1種以上の充填剤と、
(d)1種以上のシラン接着促進剤と、
(e)1種以上の一官能性ポリアルキレングリコールと、
を含有するポリウレタン接着剤組成物が提供される。
(a)第1の基材の少なくとも一部にポリウレタン接着剤組成物を塗布する工程であって、ポリウレタン接着剤組成物が、(i)イソシアネート部位を有する1種以上のウレタンプレポリマーと、(ii)触媒量の1種以上の触媒と、(iii)1種以上の充填剤と、(iv)1種以上のシラン接着促進剤と、(v)1種以上の一官能性ポリアルキレングリコールとを含有すること;
(b)第2の基材を前記第1の基材と接触させること;並びに
(c)ポリウレタン接着剤組成物を硬化させて、第1の基材と第2の基材との間に接着剤結合を形成すること;
を含む。
プレポリマー1は、MDI/PPOベースのプレポリマーである。プレポリマーは、商標名Voranol2000Lとして市販されている平均分子量が2000g/モルであるポリオキシプロピレンジオール22.571gを、商標名Arcol CP4655として市販されている平均分子量が4650g/モルであるポリオキシプロピレントリオール33.132gと混合することによって調製されるポリエーテルポリウレタンプレポリマーである。33.779gの可塑剤及び9.501gのジフェニルメタン4,4’−ジイソシアネートを加えた。その後、0.009gのメチルエチルケトン中の0.001gのオルトリン酸及び1gのジエチルマロネートを加えた。次いで、混合物全体を反応器中で50℃まで加熱し、0.007gの第一スズオクトエートを加えた。反応は50℃で1時間行った。得られたプレポリマーは、本明細書ではNCO−プレポリマーと呼ばれる。
以下の表1に示されるポリウレタン接着剤組成物を、以下の通り調製した。遊星混合物(planetary mixture)に、記載された量のPPOベースのプレポリマー1と全ての液体添加剤(DEM、シラン、Vestinol 9、Voranate M600、及びDesmodur PAG−15)を入れた。混合物を真空下室温で35分間撹拌した。その後、適切な量のカーボンブラック、炭酸カルシウム、及びAerosil R208を添加した。次いで、混合物を撹拌し、窒素雰囲気下で60〜70℃まで加熱し、その後真空下で35分間加熱した。温度が60℃を超えたら、適量のポリエステルプレポリマー2を遊星ミキサーに加え、更に10分間撹拌した。次いで、適切な量のジイソノニルフタレートをVestinol 9として加え、UL28+Vestinol触媒とDMDEE触媒を加え、真空下で、又は均一なペースト状の黒い混合物が観察されるまで、混合物を15分間撹拌した。
基材:以下のセラミックフリットタイプを使用した:SGS Ferro 14305、SGS Ferro 14502、及びPLK Johnson Mattey FERRO C 24−8708 IR−9872−L。
次いで、ガラス基材における硬化されたビードの剥離試験を、下記の表1に列挙されている以下の気候条件に従って実行した。
Claims (14)
- (a)イソシアネート部位を有する1種以上のウレタンプレポリマーと、
(b)触媒量の1種以上の触媒と、
(c)1種以上の充填剤と、
(d)1種以上のシラン接着促進剤と、
(e)1種以上の一官能性ポリアルキレングリコールと、
を含有するポリウレタン接着剤組成物。 - 前記1種以上のウレタンプレポリマーが、エチレンオキシド、プロピレンオキシド又はこれらの混合物のアルキレンオキシド単位を含むポリオールから誘導される、請求項1に記載のポリウレタン接着剤組成物。
- 前記1種以上のウレタンプレポリマーが芳香族イソシアネートから誘導される、請求項1に記載のポリウレタン接着剤組成物。
- 前記1種以上の触媒が1つ以上の三級アミン基を含む化合物から選択される、請求項1に記載のポリウレタン接着剤組成物。
- 前記1種以上の触媒がジモルホリノジアルキルエーテルから選択される、請求項4に記載のポリウレタン接着剤組成物。
- 前記1種以上の充填剤が1つ以上の形態のカーボンブラック及び1種以上の炭酸カルシウムである、請求項1に記載のポリウレタン接着剤組成物。
- 前記ポリウレタン接着剤組成物が粘土を含まない、請求項1に記載のポリウレタン接着剤組成物。
- 前記1種以上のシラン接着促進剤がアルコキシシランから選択される、請求項1に記載のポリウレタン接着剤組成物。
- 前記1種以上のポリアルキレングリコールが、C1〜C12の一官能性アルコール開始ポリアルキレンオキシド鎖であり、前記ポリアルキレンオキシド鎖が、エチレンオキシプロピルオキシ、ブチレンオキシ、又はこれらの混合物の単位を含む、請求項1に記載のポリウレタン接着剤組成物。
- 前記1種以上のポリアルキレングリコールが200〜2,000の数平均分子量を有する、請求項1に記載のポリウレタン接着剤組成物。
- (a)前記ポリウレタン接着剤組成物の重量に基づいて20〜85重量%の、イソシアネート部位を有する1種以上のウレタンプレポリマー;
(b)前記ポリウレタン接着剤組成物の重量に基づいて0.3〜3.5重量%の1種以上の触媒;
(c)前記ポリウレタン接着剤組成物の重量に基づいて15〜50重量%の1種以上の充填剤;
(d)前記ポリウレタン接着剤組成物の重量に基づいて0.1〜5重量%の1種以上のシラン接着促進剤;及び
(e)前記ポリウレタン接着剤組成物の重量に基づいて0.1〜5重量%の1種以上のポリアルキレングリコール;
を含有する、請求項1に記載のポリウレタン接着剤組成物。 - (a)前記ポリウレタン接着剤組成物の重量に基づいて30〜65重量%の、イソシアネート部位を有する1種以上のウレタンプレポリマー;
(b)前記ポリウレタン接着剤組成物の重量に基づいて0.1〜2.6重量%の1種以上の触媒;
(c)前記ポリウレタン接着剤組成物の重量に基づいて15〜23重量%の1種以上のカーボンブラック;
(d)前記ポリウレタン接着剤組成物の重量に基づいて8〜20重量の1種以上の炭酸カルシウム及び0.7〜3重量%の1種以上のシラン接着促進剤;並びに
(e)前記ポリウレタン接着剤組成物の重量に基づいて0.4〜2重量%の1種以上のポリアルキレングリコール;
を含有する、請求項8に記載のポリウレタン接着剤組成物。 - (a)第1の基材の少なくとも一部にポリウレタン接着剤組成物を塗布することであって、前記ポリウレタン接着剤組成物が、
(i)イソシアネート部位を有する1種以上のウレタンプレポリマーと、
(ii)触媒量の1種以上の触媒と、
(iii)1種以上の充填剤と、
(iv)1種以上のシラン接着促進剤と、
(v)1種以上の一官能性ポリアルキレングリコールとを含有すること;
(b)第2の基材を前記第1の基材と接触させること;並びに
(c)ポリウレタン接着剤組成物を硬化させて、前記第1の基材と前記第2の基材との間に接着剤結合を形成すること、
を含む方法。 - 前記第1の基材がガラス又はコーティングされたプラスチックである、請求項13に記載の方法。
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