JP6381473B2 - ポリウレタン粘着剤組成物およびポリウレタン粘着剤 - Google Patents
ポリウレタン粘着剤組成物およびポリウレタン粘着剤 Download PDFInfo
- Publication number
- JP6381473B2 JP6381473B2 JP2015071668A JP2015071668A JP6381473B2 JP 6381473 B2 JP6381473 B2 JP 6381473B2 JP 2015071668 A JP2015071668 A JP 2015071668A JP 2015071668 A JP2015071668 A JP 2015071668A JP 6381473 B2 JP6381473 B2 JP 6381473B2
- Authority
- JP
- Japan
- Prior art keywords
- mass
- polyol
- pentamethylene diisocyanate
- diisocyanate
- ppm
- 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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- 239000000203 mixture Substances 0.000 title claims description 94
- 239000004814 polyurethane Substances 0.000 title claims description 67
- 229920002635 polyurethane Polymers 0.000 title claims description 67
- 239000000853 adhesive Substances 0.000 title description 70
- 230000001070 adhesive effect Effects 0.000 title description 70
- 229920005862 polyol Polymers 0.000 claims description 117
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 110
- 150000003077 polyols Chemical class 0.000 claims description 99
- 239000005056 polyisocyanate Substances 0.000 claims description 80
- 229920001228 polyisocyanate Polymers 0.000 claims description 80
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 51
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 41
- -1 sheets Substances 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- 238000004821 distillation Methods 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 30
- 239000000178 monomer Substances 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 238000000034 method Methods 0.000 description 22
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- 239000012948 isocyanate Substances 0.000 description 20
- 150000001298 alcohols Chemical class 0.000 description 19
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- 150000002513 isocyanates Chemical class 0.000 description 17
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
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- 239000004417 polycarbonate Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 239000002253 acid Substances 0.000 description 7
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- 238000012360 testing method Methods 0.000 description 7
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 6
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 6
- HLFNUPJVFUAPLD-UHFFFAOYSA-M 2-ethylhexanoate;2-hydroxypropyl(trimethyl)azanium Chemical compound CC(O)C[N+](C)(C)C.CCCCC(CC)C([O-])=O HLFNUPJVFUAPLD-UHFFFAOYSA-M 0.000 description 5
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 5
- 229920002799 BoPET Polymers 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical class NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 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 4
- 230000000052 comparative effect Effects 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000002649 leather substitute Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000005829 trimerization reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
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- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 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 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical class O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
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- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 2
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-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
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- BXJWDOYMROEHEN-UHFFFAOYSA-N tributylstibane Chemical compound CCCC[Sb](CCCC)CCCC BXJWDOYMROEHEN-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQISDOIAJWWPGA-UHFFFAOYSA-N triethyl(3-hydroxypropyl)azanium Chemical compound CC[N+](CC)(CC)CCCO NQISDOIAJWWPGA-UHFFFAOYSA-N 0.000 description 1
- GZBUMTPCIKCWFW-UHFFFAOYSA-N triethylcholine Chemical compound CC[N+](CC)(CC)CCO GZBUMTPCIKCWFW-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Description
ペンタメチレンジイソシアネートの純度は、後述する製造例1で得られたペンタメチレンジイソシアネート(a)を用い、以下のGC分析条件下で得られたクロマトグラムの面積値から検量線を作成し、ペンタメチレンジイソシアネートの純度を算出した。
カラム;UADX−30(フロンティア・ラボ社製)0.25mmφ×30m、膜厚0.15μm
オーブン温度;50℃で5分間保持、50℃から200℃まで、10℃/minで昇温、200℃から350℃まで、20℃/minで昇温、350℃で7.5分間保持
注入口温度;250℃
検出器温度;250℃
He流量 ; 1.2mL/min
注入モード ; スプリット
検出方法;FID
<塩素濃度(単位:ppm>
試料を200mg秤量し、Ar/O2気流中、900℃の燃焼炉にて燃焼分解した。発生したガスを吸収液に吸収させ、イオンクロマトグラフ法にて塩素濃度を定量した。
装置:イオンクロマトグラフICS−1500(サーモフィッシャーサイエンティフィック製)
<式(1)で示される化合物の濃度(単位:ppm)>
以下の装置および条件にてGC分析し、式(1)で示される化合物の面積比率を、式(1)で示される化合物の濃度とした。
カラム;DB−5MS+DG(アジレント・テクノロジー社製)0.25mmφ×30m、膜厚0.25μm
オーブン温度;40℃で5分間保持、40℃から220℃まで、10℃/minで昇温
注入口温度;200℃
検出器温度;250℃
検出方法:FID
He流量 ; 4mL/min
注入モード ; スプリット
スプリット比:50/1
<イソシアネート基の反応率(単位:%)>
イソシアネート基の反応率は、電位差滴定装置を用いて、JIS K−1603−1(2007年)に準拠したトルエン/ジブチルアミン・塩酸法によりイソシアネート含有率を測定し、以下の式より算出した。
<イソシアネートモノマーの濃度(単位:質量%)>
後述する製造例1で得られたペンタメチレンジイソシアネート(a)または市販のヘキサメチレンジイソシアネートを標準物質として用い、ジベンジルアミンによりラベル化させ、以下のHPLC分析条件下で得られたクロマトグラムの面積値から作成した検量線により、ポリウレタン組成物中の未反応のイソシアネートモノマー(ペンタメチレンジイソシアネート、ヘキサメチレンジイソシアネート)の濃度を算出した。
1) ポンプ LC−20AT
2) デガッサ DGU−20A3
3) オートサンプラ SIL−20A
4) カラム恒温槽 COT−20A
5) 検出器 SPD−20A
カラム;SHISEIDO SILICA SG−120
カラム温度;40℃
溶離液;n−ヘキサン/メタノール/1,2−ジクロロエタン=90/5/5(体積比)
流量;0.2mL/min
検出方法;UV 225nm
<イソシアネート基含有率(単位:質量%)>
ポリイソシアネート組成物のイソシアネート基含有率は、電位差滴定装置を用いて、JIS K−1603−1(2007年)に準拠したトルエン/ジブチルアミン・塩酸法により、測定した。
国際公開パンフレットWO2012/121291号の明細書における実施例1と同様の操作にて、99.9質量%のペンタメチレンジイソシアネート(a)(以後PDI(a)と略する場合がある。)を得た。
PDI(a)を以下のGC−MS分析条件で測定した結果、MSスペクトルのフラグメントイオンとしてm/z:55、68、85、112にピークを持ち、148、150の強度比が約3対1であり、1原子中に塩素原子を1つ持つ化合物が検出され、式(1)で表される化合物と推定した。
装置;Q1000GC K9(日本電子社製)
イオン化法;EI、CI
カラム;DB−5MS+DG(アジレント・テクノロジー社製)0.25mmφ×30m、膜厚0.25μm
オーブン温度;40℃で5分間保持、40℃から220℃まで、10℃/minで昇温
注入口温度;200℃
検出器温度;250℃
He流量 ; 4mL/min
注入モード ; スプリット
スプリット比;50/1
イオン源温度;200℃
イオン化電流;200μA
製造例2(ペンタメチレンジイソシアネート(b)の製造)
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率35〜80%の留分を採取した。得られたペンタメチレンジイソシアネート(b)の純度は99.9質量%、塩素濃度は14ppm、式(1)で示される化合物の濃度は24ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率13〜80%の留分を採取した。得られたペンタメチレンジイソシアネート(c)の純度は99.8質量%、塩素濃度は477ppm、式(1)で示される化合物の濃度は1103ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率20〜70%の留分を採取した。得られたペンタメチレンジイソシアネート(c)の純度は99.9質量%、塩素濃度は8ppm、式(1)で示される化合物の濃度は31ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率20〜88%の留分を採取した。得られたペンタメチレンジイソシアネート(e)の純度は99.9質量%、塩素濃度は511ppm、式(1)で示される化合物の濃度は386ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率35〜70%の留分を採取した。得られたペンタメチレンジイソシアネート(f)の純度は99.9質量%、塩素濃度は7ppm、式(1)で示される化合物の濃度は28ppmであった。
製造例1記載のペンタメチレンジイソシアネート(a1)を、製造例1と同様の操作にて精留し、留出率13〜88%の留分を採取した。得られたペンタメチレンジイソシアネート(g)の純度は99.8質量%、塩素濃度は562ppm、式(1)で示される化合物の濃度は1037ppmであった。
以下の方法により、ペンタメチレンジイソシアネートのイソシアヌレート誘導体を得た。
以下の方法により、ペンタメチレンジイソシアネートのイソシアヌレート誘導体を得た。
以下の方法により、ペンタメチレンジイソシアネートのイソシアヌレート誘導体を得た。
以下の方法により、ペンタメチレンジイソシアネートのビウレット誘導体を得た。
以下の方法により、ペンタメチレンジイソシアネートのアロファネート誘導体を得た。
以下の方法により、ペンタメチレンジイソシアネートのポリオール誘導体を得た。
表2記載のポリイソシアネート化合物を用いた以外は、合成例1と同様の操作にてポリイソシアネート組成物(g)〜(i)を得た。
以下の方法により、ヘキサメチレンジイソシアネートのイソシアヌレート誘導体を得た。
撹拌機、温度計、還流冷却装置、および、窒素導入管を備えた4つ口フラスコに、有機溶剤として酢酸エチルを500質量部仕込み、窒素置換しながら70℃に加熱昇温した。次いでこの中に、重合可能な単量体として、2−エチルヘキシルアクリレートを500質量部、6−ヒドロキシヘキシルアクリレート10質量部と重合開始剤としてアゾイロブチロニトリルを0.4質量部の混合液を4時間かけてフィードした。フィード終了より1時間後にAIBNを0.1質量部添加した。AIBNの添加後より2時間反応させポリオール(a)を得た。
実施例1(粘着剤組成物(A)、粘着剤(A)の製造)
合成例14で得られたポリオール(a)を100質量部、合成例1で得られたポリイソシアネート組成物(a)を1.1質量部配合し、23℃で2分間撹拌混合し、粘着剤組成物(A)を得た。なお、この配合において、ポリオールのヒドロキシ基に対する、ポリイソシアネートのイソシアネート基の当量比(NCO/OH)は、0.5であった。
ポリイソシアネート組成物(a)に代え、表3記載のポリイソシアネート組成物を、表3記載の質量部用いた以外は、実施例1と同様の操作にて粘着剤組成物(B)〜(M)、および、粘着剤(B)〜(M)を得た。
各実施例および各比較例で得られた粘着剤の初期の粘着力、湿熱試験後の粘着力、粘着保持率およびゲル分率を、以下の方法で測定した。その結果を表3に示す。
PETフィルム(A)の粘着剤を25mm幅に切断した後、離型フィルムを剥がし、偏光板に2kgローラーを転がして圧着した。23℃、相対湿度50%の室内にて1時間静置後、引張試験機を用いて、引張速度30m/min、剥離角度180℃にて初期の粘着力を測定した。
PETフィルム(A)の粘着剤を25mm幅に切断した後、離型フィルムを剥がし、偏光板に2kgローラーを転がして圧着した。23℃、相対湿度50%の室内にて1時間静置後、60℃、相対湿度90%の湿熱恒温槽に5日保持した。その後、23℃、相対湿度50%の室内にて1時間静置した後、引張試験機を用いて、引張速度30m/min、剥離角度180℃にて湿熱試験後の粘着力を測定した。
粘着保持率を、以下の式により求めた。
なお、粘着保持率が100%未満である場合には、湿熱試験によって粘着力が低下したことを示し、その数値が低いほど、耐久性に劣ることを示す。
PETフィルム(B)の粘着剤を幅10cm、長さ20cmに切断した。PETフィルム(B)および離型フィルムを剥がし粘着剤の重量を測定しW1とした。次いで、アセトンに含浸し23℃の室内で24時間静置した。その後、粘着剤を80℃の恒温槽で3時間乾燥させた後の重量を測定しW2とした。以下の式によりゲル分率を算出した。
なお、ゲル分率が100%に近いほど、剥離時において、糊残りが生じ難いことを示す。
Claims (4)
- ペンタメチレンジイソシアネートおよび/またはその誘導体を含むポリイソシアネートと、
ポリオールと
を含有することを特徴とする、ポリウレタン粘着剤組成物。 - 前記ポリイソシアネートの塩素濃度が、10ppm以上500ppm以下であることを特徴とする、請求項1に記載のポリウレタン粘着剤組成物。
- 請求項1〜3のいずれか一項に記載のポリウレタン粘着剤組成物から形成されることを特徴とする、ポリウレタン粘着剤。
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