JP6703995B2 - 耐薬品性ポリウレタン接着剤 - Google Patents
耐薬品性ポリウレタン接着剤 Download PDFInfo
- Publication number
- JP6703995B2 JP6703995B2 JP2017538413A JP2017538413A JP6703995B2 JP 6703995 B2 JP6703995 B2 JP 6703995B2 JP 2017538413 A JP2017538413 A JP 2017538413A JP 2017538413 A JP2017538413 A JP 2017538413A JP 6703995 B2 JP6703995 B2 JP 6703995B2
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane
- sensitive adhesive
- polyol
- solution
- groups
- 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.)
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- 239000004814 polyurethane Substances 0.000 title claims description 107
- 229920002635 polyurethane Polymers 0.000 title claims description 103
- 230000001070 adhesive effect Effects 0.000 title description 41
- 239000000853 adhesive Substances 0.000 title description 39
- 239000000126 substance Substances 0.000 title description 21
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 86
- 229920005862 polyol Polymers 0.000 claims description 77
- 150000003077 polyols Chemical class 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 21
- 239000005056 polyisocyanate Substances 0.000 claims description 20
- 229920001228 polyisocyanate Polymers 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 238000010030 laminating Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 48
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 42
- 125000003118 aryl group Chemical group 0.000 description 40
- 239000002987 primer (paints) Substances 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 229920005906 polyester polyol Polymers 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- 229920000728 polyester Polymers 0.000 description 31
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000012948 isocyanate Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 19
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 239000004417 polycarbonate Substances 0.000 description 17
- 229920000515 polycarbonate Polymers 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 229910001220 stainless steel Inorganic materials 0.000 description 11
- 239000010935 stainless steel Substances 0.000 description 11
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 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 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000004971 Cross linker Substances 0.000 description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 7
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 229920001610 polycaprolactone Polymers 0.000 description 6
- 239000004632 polycaprolactone Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229920003232 aliphatic polyester Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000010382 chemical cross-linking Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000013615 primer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
- ZIZJPRKHEXCVLL-UHFFFAOYSA-N 1,3-bis(6-isocyanatohexyl)-1,3-diazetidine-2,4-dione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C1=O ZIZJPRKHEXCVLL-UHFFFAOYSA-N 0.000 description 1
- UFXYYTWJETZVHG-UHFFFAOYSA-N 1,3-diisocyanatobutane Chemical compound O=C=NC(C)CCN=C=O UFXYYTWJETZVHG-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-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
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- BUYHVRZQBLVJOO-UHFFFAOYSA-N 2-ethyl-2,4-dimethylhexane-1,3-diol Chemical compound CCC(C)C(O)C(C)(CC)CO BUYHVRZQBLVJOO-UHFFFAOYSA-N 0.000 description 1
- LTPOFBPKMDYSSL-UHFFFAOYSA-N 2-ethylcyclohexane-1,4-dicarboxylic acid Chemical compound CCC1CC(C(O)=O)CCC1C(O)=O LTPOFBPKMDYSSL-UHFFFAOYSA-N 0.000 description 1
- DCHCHXYBRSBAIS-UHFFFAOYSA-N 2-methylcyclohexane-1,4-dicarboxylic acid Chemical compound CC1CC(C(O)=O)CCC1C(O)=O DCHCHXYBRSBAIS-UHFFFAOYSA-N 0.000 description 1
- WTKWFNIIIXNTDO-UHFFFAOYSA-N 3-isocyanato-5-methyl-2-(trifluoromethyl)furan Chemical compound CC1=CC(N=C=O)=C(C(F)(F)F)O1 WTKWFNIIIXNTDO-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- PNCLJCXGTBTEEL-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2,4-bis(trichloromethyl)-1h-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1(C(Cl)(Cl)Cl)N=CN=C(C(Cl)(Cl)Cl)N1 PNCLJCXGTBTEEL-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- DTWMQTQOFUIYKV-UHFFFAOYSA-N CCC(CC)(NC)OC Chemical compound CCC(CC)(NC)OC DTWMQTQOFUIYKV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
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- 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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Description
nは、少なくとも2、3、4、又は5であり、エステル置換基は、オルト−位又はメタ−位で環に結合している]を有する。
剥離接着強度
調製した各粘着テープサンプルから、寸法12.7mm×127mmで、均一な試験ストリップを切り出してサンプルを調製した。各実施例及び比較例のテープサンプル用に、複製を2つ作製した。次に、試験ストリップの露出させた接着剤面を、実測値:幅5.1cm×長さ12.7cm×厚さ0.12cmのステンレス鋼(SS)プレート(ChemInstruments,Incorporated,Fairfield,OHから入手した304型、BA仕上げ)の長さ方向に沿って貼り付け、2.0kgのゴム性ローラーを5往復させて、ストリップをプレートに密着させた。テープの適用前に、ティッシュペーパー(商品名KIMWIPE,Kimberly−Clark Corporation,Irving,TXから入手可能)を使用してプレートをアセトンで1回、ヘプタンで3回拭き取り洗浄した。室温(RT)かつ相対湿度(RH)50%にて1時間及び24時間なじませたあと、1000Nロードセルを取り付けた引張試験機(MTS Insight,MTS Systems,Corporation,Eden Prairie,MNから入手可能)を使用して、300mm/minのクロスヘッド速度、下部つかみ具及上部つかみ具で把持した試験片に対し180°の角度にて、剥離接着強度を評価した。2枚の試験片の平均をN/decimeter(N/dm)で記録した。この数値は、それぞれ、「室温で1時間放置したあとの、ステンレス鋼に対する剥離強度」及び「室温で24時間放置したあとの、ステンレス鋼に対する剥離強度」で報告するとおりのものであった。
調製した各接着剤転写テープサンプルから、寸法0.5インチ×0.5インチ(1.27cm×1.27cm)で試験ストリップを切り出してサンプルを調製した。次に、片面上の剥離ライナーを取り外し、試験片をペトリ皿の底面に固定した。試験ストリップの第2の露出面から剥離ライナを取り外し、このサンプル試験ストリップを内側に固定されたペトリ皿を室温(約23℃)に15分間放置した。次に、試験ストリップを、オレイン酸、又はイソプロピルアルコール及び水の重量比70:30(IPA/H2O)の混合液に70℃で8時間浸漬した。以下のガイドラインにより、接着剤サンプルの、オレイン酸、又はIPA/H2O混合液に対する抵抗性を採点し、記録した。
ゲル浸透クロマトグラフィー(GPC)により化合物の分子量分布を評価した。Waters Corporation(Milford,MA,USA)から得たGPC装置には、高圧液体クロマトグラフィーポンプ(Model 1515HPLC)、オートサンプラー(Model 717)、紫外線検出器(Model 2487)、及び屈折率検出器(Model 2410)が含まれた。クロマトグラフには、Varian Inc.(Palo Alto,CA,USA)から市販の5マイクロメートルのPL gel MIXED−Dカラムを2個取り付けた。
ARES G2平行平板レオメーター(TA Instruments)を使用して各サンプルの動的機械分析(DMA)を行い、温度の関数として各サンプルの物理特性を評価した。各サンプルに関し、レオメーターの直径8mmの平行平板の間、中央に約0.1gのポリマー材料を配置し、サンプルの縁が上部平板及び下部平板の縁と揃うようになるまで圧縮した。レオメーターの平行平板及びシャフトを取り囲む加熱炉の扉を閉め、温度を100℃にまで上昇させ、5分間維持して、残存している応力を弛緩させた。次に、軸力を0に設定して材料及び平板間の接触を維持した。温度を−50℃に設定し、次に−50℃から200℃まで5℃/minの速度で上昇させつつ、周波数1Hz、初期ひずみの振幅の0.15%で平行平板を振動させた。測定されるトルクが1g−cmに低下したときは、最大ひずみ振幅を10%として、ひずみを現在の値の50%分増加させた。25℃を含む様々な温度下での貯蔵弾性率(G’)及びTgを記録した。
以下の例は、構成要素についてのすべての好適な選択肢の包括的な実施形態を提供することを意図せずに、本発明の有用性を示す。実施例1〜16(E1〜E16)は感圧接着剤(PSA)組成物を提供するのに対し、本発明の範囲外の比較例(CE1〜CE5)は組成物を提供する。プライマー実施例17〜24(E17〜E24)は、プライマーコートとしてPSAを使用する際の組成物を提供する。実施例25〜38(E25〜E38)は、PSAの実施例とプライマーの実施例とを組み合わせて提供し、この組み合わせにより生じた剥離強度及び耐薬品性を報告する。比較例CE6及びCE7は、本発明の範囲外の接着剤及びプライマーの組み合わせを示す。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルとを入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液と、3.32gのIPDIとを加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、52.0gの酢酸エチルを加えて固体含量を最大35重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルとを入れた。溶液を75℃に加熱したあと、次に撹拌しながら0.06gの10重量% DBTDA/酢酸エチル溶液と、3.66gのTMXDIとを加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、52.5gの酢酸エチルを加えて固体含量を最大35重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルとを入れた。溶液を75℃に加熱したあと、次に撹拌しながら0.06gの10重量% DBTDA/酢酸エチル溶液と、2.52gのHDIとをに加熱し加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、50.4gの酢酸エチルを加えて固体含量を最大35重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルとを入れた。溶液を75℃に加熱したあと、次に撹拌しながら0.06gの10重量% DBTDA/酢酸エチル溶液と、3.67gのIPDIとを加えた。NCO含有量が、標準ジブチルアミン逆滴定法により決定された理論NCO値に達するまで、温度を75±2℃に維持した。理論NCO値が得られたならば、次に、0.13gのTMPを加えてポリウレタンをわずかに架橋し、NCO基がFT−IRで全く観察されなくなるまで反応させた。次に、24.0gの酢酸エチルを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液と、3.83gのIPDIとを加えた。NCO含有量が、標準ジブチルアミン逆滴定法により決定された理論NCO値に達するまで、温度を75±2℃に維持した。理論NCO値が得られたならば、次に、0.20gのTMPを加えてポリウレタンをわずかに架橋し、NCO基がFT−IRで全く観察されなくなるまで反応させた。次に、25.0gの酢酸エチルを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液と、4.0gのIPDIとを加えた。NCO含有量が、標準ジブチルアミン逆滴定法により決定された理論NCO値に達するまで、温度を75±2℃に維持した。理論NCO値が得られたならば、次に、0.268gのTMPを加えてポリウレタンをわずかに架橋し、NCO基がFT−IRで全く観察されなくなるまで反応させた。次に、45.8gの酢酸エチルを加えて固体含量を最大38重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液と、4.33gのIPDIとを加えた。NCO含有量が、標準ジブチルアミン逆滴定法により決定された理論NCO値に達するまで、温度を75±2℃に維持した。理論NCO値が得られたならば、次に、0.40gのTMPを加えてポリウレタンをわずかに架橋し、NCO基がFT−IRで全く観察されなくなるまで反応させた。次に、46.0gの酢酸エチルを加えて固体含量を最大38重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液と、4.40gのTXMDIとを加えた。NCO含有量が、標準ジブチルアミン逆滴定法により決定された理論NCO値に達するまで、温度を75±2℃に維持した。理論NCO値が得られたならば、次に、0.27gのTMPを加えてポリウレタンをわずかに架橋し、NCO基がFT−IRで全く観察されなくなるまで反応させた。次に、54.0gの酢酸エチルを加えて固体含量を最大35重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液、1.099gのTMXDI、及び2.33gのIPDIを加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、44.5gの酢酸エチルを加えて固体含量を最大38重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDL−酢酸エチル溶液、3.75gのDESMODUR 2460 Mを加えた。2時間撹拌したあと、20gの酢酸エチルで希釈して系の粘度を調節した。約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで、温度を75℃に維持した。最後に、11.50gの酢酸エチルを加えて固体含量を最大45重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、50.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gのMEKと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら2.8gの1wt% DBTDA−MEK溶液と、6.26gのMondur MLQとを加えた。2時間の反応後、20.0gのMEKで希釈して系の粘度を調節した。約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで、温度を75℃に維持した。最後に、26.5gのMEKを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.09gの10wt% DBTDL−酢酸エチル溶液、4.13gのDESMODUR 2460 Mを加えた。2時間撹拌したあと、20gの酢酸エチルで希釈して系の粘度を調節し、0.1342gのTMPを加えてポリウレタンをわずかに架橋した。約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで、温度を75℃に維持した。最後に、11.50gの酢酸エチルを加えて固体含量を最大45重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、40.0gのヒドロキシル基を末端にもつポリカプロラクトンCAPA 2200(ヒドロキシル価56mg KOH/g)と、50.0gのMEKと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.09gの10wt% DBTDA−MEK溶液と、4.98gのMONDUR MLQとを加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、26.0gのMEKを加えて固体含量を最大37重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)、1.04gのDMPA、及び10.0gのMEKを入れた。この溶液を75℃に加熱したあと、撹拌しながら2.95gの1wt% DBTDA−MEK溶液と、7.99gのMondur MLQとを加えた。2時間の反応後、20.0gのMEK及び20.0gのPH−56を加え、75℃で約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで撹拌した。最後に、29.0gのMEKを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)、1.83gのDMPA、及び10.0gのMEKを入れた。この溶液を75℃に加熱したあと、撹拌しながら3.0gの1重量% DBTDA−MEK溶液と、9.37gのMondur MLQ(NCO/OH=0.98)とを加えた。2時間の反応後、20.0gのMEK及び20.0gのPH−56を加え、75℃で約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで撹拌した。最後に、32.0gのMEKを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
CE1は、3M Company Saint Paul,MNから得た、商品名3M 93005LEの市販のダブルコートアクリルテープPSA製品とした。
CE2は、100gのDISPERCOLL U42と1.0gのBAYHYDUR 302とを、ガラスジャー内で、300〜500rpmにて10分間機械的に混合することにより調製した。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、40.0gのヒドロキシル基を末端にもつポリプロピレングリコールArcolポリオールPPG 2000(ヒドロキシル価56mg KOH/g)、0.54gのTMP及び50.0gのMEKを入れた。この溶液を75℃に加熱したあと、撹拌しながら0.09gの10wt% DBTDA−MEK溶液と、6.48gのMondur MLQとを加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、30.0gのMEKを加えて固体含量を最大37重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)、3.28gのDMPA、及び10.0gのMEKを入れた。この溶液を75℃に加熱したあと、撹拌しながら3.26gの1wt% DBTDA−MEK溶液と、11.99gのMondur MLQとを加えた。2時間の反応後、20.0gのMEK及び20.0gのPH−56を加え、75℃で約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで撹拌した。最後に、35.0gのMEKを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)、4.9gのDMPA、及び10.0gのMEKを入れた。この溶液を75℃に加熱したあと、撹拌しながら3.5gの1wt% DBTDA−MEK溶液と、14.95gのMondur MLQとを加えた。2時間の反応後、20.0gのMEK及び20.0gのPH−56を加え、75℃で約10時間、あるいはFT−IRにより遊離NCO基が観察されなくなるまで撹拌した。最後、40.0gのMEKを加えて固体含量を最大50重量%に調節し、濁りのない透明なポリウレタンPSA溶液を得た。
90部のイソオクチルアクリレート(IOA)、10部のアクリル酸(AA)、及び0.04部の2,2−ジメトキシ−2−フェニルアセトフェノン光開始剤(Irgacure TM 651,Ciba Geigy Corp.から入手)を使用してプレミックスを調製した。この混合物を窒素リッチの雰囲気下で紫外線に暴露して部分重合させて、粘度が約3000cpsのコーティング可能なシロップを準備した。0.15部の2,6−ビス−トリクロロメチル−6−(4−メトキシフェニル)−s−トリアジン及び更に0.16部のIrgacure(商標)651をシロップに加えた。この材料からテープを調製するに当たり、次にシロップを2mil(約51マイクロメートル)PETフィルムに2milの厚みでナイフコートした。次に、得られた複合体を、窒素リッチな環境下で、スペクトル出力300〜400nm、最大で351nmの紫外線に暴露した。暴露時間の最初の1/3では約1.0mW/cm2の強度を使用し、暴露時間の次の2/3では約2.2mW/cm2の強度を使用し、総エネルギーを250mJ/cm2とした。
E10のTg=12.3℃
E13のTg=−42℃
本発明のポリウレタン組成物は、更に、ポリウレタン又はその他のポリエステル/ポリエーテル系接着剤用の溶剤型プライマーとしても使用できる。この目的で、これらの実施例では、頭部が長方形のスワブ(Texwipe(商標)Kernersville,NC,USAのCleanTips(商標)スワブ)を使用して、表面をコートするのに最低限の量のポリウレタン希釈液を、手作業によりステンレス鋼パネルに塗布した。プライマーコーティングを室温で10分間乾燥させたあと、テープに塗布した。
実施例10(E10)溶液の一部を、MEK溶媒により固形分5重量%に希釈して、濁りのない透明なポリウレタンPSAプライマー溶液を得た。
機械的撹拌子、凝縮器、及び窒素導入口を取り付けた樹脂製反応容器に、30.0gのヒドロキシル基を末端にもつポリエステルPH−56(ヒドロキシル価56mg KOH/g)と、10.0gの酢酸エチルと、を入れた。この溶液を75℃に加熱したあと、撹拌しながら0.06gの10wt% DBTDA−酢酸エチル溶液と、3.66gのTMXDIとを加えた。FT−IRにより遊離NCO基が観察されなくなるまで、温度を75±2℃に維持した。次に、MEKを加えて固体含量を最大5重量%に調節し、濁りのない透明なプライマー溶液を得た。
E11溶液の一部を、MEK溶媒により固形分5重量%に希釈して、濁りのない透明なポリウレタンPSAプライマー溶液を得た。
E14溶液の一部を、MEK溶媒により固形分5重量%に希釈して、濁りのない透明なポリウレタンPSAプライマー溶液を得た。
E15溶液の一部を、MEK溶媒により固形分5重量%に希釈して、濁りのない透明なポリウレタンPSAプライマー溶液を得た。
100部の乾燥E14ポリマーを基準として5部の2,4−ペンタンジオン酸アルミニウム(AlAcAc)をE21溶液に加えた。カルボキシル酸を存在させることで、化学的架橋に機能する機能部分が提供され、これによりポリウレタン及びプライマー組成物の耐温度性及び耐薬品性が向上され得る。
CE4溶液の一部を、MEK溶媒により固形分5重量%に希釈して、濁りのない透明なポリウレタンPSAプライマー溶液を得た。
CE5溶液の一部を、MEK溶媒により固形分5重量%に希釈して、濁りのない透明なポリウレタンPSAプライマー溶液を得た。
上記の「引きはがし粘着力」試験に記載のとおりに剥離接着強度試験を実施した。
Claims (3)
- ポリイソシアネート成分と、ポリオール成分と、官能性酸含有化合物との反応生成物を含むポリウレタンポリマーを含む感圧接着剤組成物であって、
前記ポリオール成分が10〜14(cal/cm3)1/2の範囲の全溶解度パラメーターを有し、
前記官能性酸含有化合物が、一般式(HX) 2 R 1 A[式中、Aは、−CO 2 M、−OSO 3 M、−SO 3 M、−OPO(OM) 2 、−PO(OM) 2 から選択される官能性酸基であり、Mは、H又はカチオンであり、Xは、O、S、NH又はNRであり、Rは炭素原子を1〜4個含むアルキレン基であり;R 1 は、価数が少なくとも3である有機結合基であり、炭素原子を1〜50個含み、場合により、第3級窒素、エーテル酸素、又はエステル酸素原子を1個以上含み、イソシアネート反応性水素含有基は含まない]により表され、
前記ポリウレタンポリマーが、100gあたり0.001〜37mmolの官能性酸基Aを含む、感圧接着剤組成物。 - ポリウレタンポリマーを含む感圧接着剤組成物であって、前記ポリウレタンポリマーが、
25℃で液体であるポリイソシアネートを含むポリイソシアネート成分と、
オルト−又はメタ−フタレートの繰り返し単位と、炭素原子を少なくとも4個含むアルキレン基の繰り返し単位を含む、ポリオール成分と、
の反応生成物を含み、25℃及び周波数1ヘルツにて1MPa未満のG’を有する、感圧接着剤組成物。 - 基材と、
前記基材の主表面上に配置された、請求項2に記載の感圧接着剤組成物の層と、
を含む、ラミネートテープ。
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KR102528693B1 (ko) | 2023-05-08 |
CN107429140B (zh) | 2021-03-16 |
EP3872145A1 (en) | 2021-09-01 |
KR20170107496A (ko) | 2017-09-25 |
EP3247759B1 (en) | 2021-05-05 |
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