JP7306597B1 - 接着剤、積層体、積層体の製造方法、包装材 - Google Patents
接着剤、積層体、積層体の製造方法、包装材 Download PDFInfo
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- JP7306597B1 JP7306597B1 JP2023511633A JP2023511633A JP7306597B1 JP 7306597 B1 JP7306597 B1 JP 7306597B1 JP 2023511633 A JP2023511633 A JP 2023511633A JP 2023511633 A JP2023511633 A JP 2023511633A JP 7306597 B1 JP7306597 B1 JP 7306597B1
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- Prior art keywords
- polyol
- acid
- composition
- polyisocyanate
- adhesive
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 60
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 60
- 239000005022 packaging material Substances 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000003077 polyols Chemical class 0.000 claims abstract description 121
- 229920005862 polyol Polymers 0.000 claims abstract description 113
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 65
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims abstract description 8
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims description 45
- 239000012790 adhesive layer Substances 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 25
- 238000000576 coating method Methods 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 23
- 229920005906 polyester polyol Polymers 0.000 claims description 20
- 229920000570 polyether Polymers 0.000 claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 18
- 229920000768 polyamine Polymers 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000010030 laminating Methods 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 claims description 3
- ULMZOZMSDIOZAF-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)propanoic acid Chemical compound OCC(CO)C(O)=O ULMZOZMSDIOZAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 abstract description 32
- 239000002184 metal Substances 0.000 abstract description 32
- 239000007788 liquid Substances 0.000 abstract description 14
- 239000011888 foil Substances 0.000 abstract description 7
- -1 polymethylene Polymers 0.000 description 60
- 239000004014 plasticizer Substances 0.000 description 38
- 239000000049 pigment Substances 0.000 description 36
- 239000010410 layer Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000565 sealant Substances 0.000 description 16
- 229910052782 aluminium Inorganic materials 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 229920002799 BoPET Polymers 0.000 description 11
- 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 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 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 9
- 239000012948 isocyanate Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- 238000007789 sealing Methods 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 230000001588 bifunctional effect Effects 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 238000003475 lamination Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 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
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 229920006284 nylon film Polymers 0.000 description 5
- 229920001515 polyalkylene glycol Polymers 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 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
- 229910052748 manganese Inorganic materials 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical class C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- AIFLGMNWQFPTAJ-UHFFFAOYSA-J 2-hydroxypropanoate;titanium(4+) Chemical compound [Ti+4].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O AIFLGMNWQFPTAJ-UHFFFAOYSA-J 0.000 description 2
- LVAGMBHLXLZJKZ-UHFFFAOYSA-N 2-o-decyl 1-o-octyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC LVAGMBHLXLZJKZ-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- TUZMHNASXCXMBO-UHFFFAOYSA-N 3-methylpentane-2,2-diol Chemical compound CCC(C)C(C)(O)O TUZMHNASXCXMBO-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
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- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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Abstract
Description
本発明の接着剤はポリイソシアネート組成物(X)と、ポリオール組成物(Y)と、を含む2液硬化型である。以下、本発明の接着剤について詳細に説明する。
(ポリイソシアネート化合物(A))
ポリイソシアネート組成物(X)は、複数のイソシアネート基を有するポリイソシアネート化合物(A)を含む。ポリイソシアネート化合物(A)としては特に限定されず、芳香族ジイソシアネート、芳香脂肪族ジイソシアネート、脂肪族ジイソシアネート、脂環族ジイソシアネート、及びこれらジイソシアネートのビュレット体、ヌレート体、アダクト体、アロファネート体、カルボジイミド変性体、ウレトジオン変性体、これらポリイソシアネートとポリオールを反応させたウレタンプレポリマー等が挙げられ、これらを単独でまたは複数組み合わせて使用することができる。
ダイマージオール;
ビスヒドロキシエトキシベンゼン;
ジエチレングリコール、トリエチレングリコール、その他のポリエチレングリコール、ポリプロピレングリコール、ポリブチレングリコール等のポリアルキレングリコール;
ポリアルキレングリコールを更に芳香族又は脂肪族ポリイソシアネートで高分子量化したウレタン結合含有ポリエーテルポリオール;
プロピオラクトン、ブチロラクトン、ε-カプロラクトン、σ-バレロラクトン、β-メチル-σ-バレロラクトン等の環状エステル化合物の開環重合反応によって得られるポリエステルと、グリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール等の多価アルコールとの反応物であるポリエステルポリオール等が挙げられる。
ポリイソシアネート(a1-1)は4,4’-ジフェニルメタンジイソシアネートを含むが、他のポリイソシアネート化合物を含んでいてもよい。4,4’-ジフェニルメタンジイソシアネートと併用可能なポリイソシアネート化合物としては特に制限されず、ポリイソシアネート化合物(A)として例示したものを1種または2種以上組み合わせて用いることができる。ポリイソシアネート(a1-1)に占める4,4’-ジフェニルメタンジイソシアネートの配合量は、40~99質量%であることが好ましく、75~90質量%であることが好ましい。
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC-8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
ポリイソシアネート組成物(X)は、ウレタンプレポリマー(A1)以外のイソシアネート化合物(A2)を含んでいてもよい。イソシアネート化合物(A2)としては、ポリイソシアネート化合物(A)として例示したものを適宜用いることができる。カルボジイミド変性ジイソシアネートやポリメチレンポリフェニルポリイソシアネート(ポリメリックMDI、あるいはクルードMDIとも称される)が好ましい。
(ポリオール(B))
本発明に用いられるポリオール(B)としては特に限定されず、エチレングリコール、プロピレングリコール、1,3-プロパンジオール、1,4-ブタンジオール、1,5-ペンタンジオール、3-メチル-1,5-ペンタンジオール、1,6-ヘキサンジオール、ネオペンチルグリコール、メチルペンタンジオール、ジメチルブタンジオール、ブチルエチルプロパンジオール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、トリプロピレングリコール、ビスヒドロキシエトキシベンゼン、1,4-シクロヘキサンジオール、1,4-シクロヘキサンジメタノール、トリエチレングリコール等のグリコール;
グリセリン、トリメチロールプロパン、ペンタエリスリトール、ポリプロピレングリコールのトリオール体等の3官能又は4官能の脂肪族アルコール;
ビスフェノールA、ビスフェノールF、水素添加ビスフェノールA、水素添加ビスフェノールF等のビスフェノール;
ダイマージオール;
前記グリコール、ダイマージオール、又は前記ビスフェノール等の2官能型ポリオールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(2);
前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(3);
前記グリコール、ダイマージオール、又は前記ビスフェノール等の2官能型ポリオールと、前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(4);
ジメチロールプロピオン酸、ひまし油脂肪酸等のヒドロキシル酸の重合体である、ポリエステルポリオール(5);
前記ポリエーテルポリオールと、前記グリコール、ダイマージオール、ビスフェノール等の2官能型ポリオール、3官能又は4官能の脂肪族アルコールからなる群から選ばれる少なくとも一種と、多価カルボン酸とを反応させて得られるポリエーテルポリエステルポリオール;
40℃程度の比較的低温での加温でも塗工性に優れた接着剤となることからポリオール(B)はポリエーテルポリオール(B1)または植物油ポリオール(B2)の少なくとも一種を含むことが好ましい。塗工適性の観点から、ポリオール(B)におけるポリエーテルポリオール(B1)または植物油ポリオール(B2)の配合量は、20質量%以上であることが好ましく、30質量%であることがより好ましい。100質量%であってもよいが、より好ましくは80質量%以下である。
本発明において、ポリオール(B)はポリエステルポリオール(B3)を含むことが好ましい。これにより、ナイロンフィルムなどの硬質フィルムとの接着性を向上させることができる。
本発明に用いられる化合物(C)は、2,2-ジメチロール酢酸、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸、2,2-ジメチロールペンタン酸からなる群から選ばれる少なくとも一種であり、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸の少なくとも一種を含むことが好ましく、2,2-ジメチロールプロピオン酸を含むことがより好ましい。ポリオール組成物(Y)が化合物(C)を含むことにより、金属基材への密着性、ポットライフに優れた接着剤とすることができる。
ポリオール組成物(Y)は、複数のアミノ基を有するポリアミン(D)を含むことが好ましい。本明細書においてアミノ基とは、NH2基またはNHR基(Rは官能基を有していてもよいアルキル基またはアリール基)をいう。ポリオール組成物がポリアミン(D)を含むことにより、またバリア性の基材を貼り合わせる場合にも外観が良好な積層体を得ることができる。
本発明の接着剤は必要に応じて触媒を使用することにより硬化反応を促進することができる。触媒としては、ポリイソシアネート組成物(X)とポリオール組成物(Y)のウレタン化反応を促進するものであれば特に制限されず、金属系触媒(E1)、脂肪族環状アミド化合物(E2)等が例示される。
本発明の接着剤は、必要に応じて顔料を含んでいてもよい。用いられる顔料としては特に制限はなく、塗料原料便覧1970年度版(日本塗料工業会編)に記載されている体質顔料、白顔料、黒顔料、灰色顔料、赤色顔料、茶色顔料、緑色顔料、青顔料、金属粉顔料、発光顔料、真珠色顔料等の有機顔料や無機顔料、さらにはプラスチック顔料などが挙げられる。
本発明の接着剤は、接着促進剤を含んでいてもよい。接着促進剤としては、シランカップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤等のカップリング剤、エポキシ樹脂等が挙げられる。
本発明の接着剤は、上述した成分以外に、レベリング剤、コロイド状シリカやアルミナゾルなどの無機微粒子、ポリメチルメタクリレート系の有機微粒子、消泡剤、タレ性防止剤、湿潤分散剤、粘性調整剤、紫外線吸収剤、金属不活性化剤、過酸化物分解剤、難燃剤、補強剤、可塑剤、潤滑剤、防錆剤、蛍光性増白剤、無機系熱線吸収剤、防炎剤、帯電防止剤、脱水剤、公知慣用の熱可塑性エラストマー、粘着付与剤、燐酸化合物、メラミン樹脂、反応性エラストマー等を含んでいてもよい。これらの添加剤の配合量は、本発明の接着剤の希望を損なわない範囲で適宜調整される。
本発明の積層体は、公知の方法で得ることができる。例えばポリイソシアネート組成物(X)とポリオール組成物(Y)とを事前に混ぜ合わせた後、第一の基材に塗布し、次いで塗布面に第二の基材を積層し、接着剤層を硬化させて得る2液混合工程を有する方法や、ポリイソシアネート組成物(X)と、組成物ポリオール(Y)とを第一の基材及び第二の基材に別々に塗布後、それぞれの塗布面を接触させ圧着させることにより第一の基材と第二の基材とを積層させ、接着剤層を硬化させて得る2液分別塗工工程を有する方法により得られる。
本発明の積層体は、複数の基材を上述の方法にて貼り合わせて得られる。また、本発明の積層体に、さらに他の基材を貼り合わせることもできる。この際用いる接着剤は上述のものであってもよいし、汎用の2液硬化型接着剤であってもよい。また、本発明の方法で得られた積層体にさらに他の基材を貼り合わせる場合、ドライラミネート法またはノンソルベントラミネート法を用いてもよいし、分別塗工方法を用いてもよい。
(1)基材1/接着層1/シーラントフィルム
(2)基材1/接着層1/金属蒸着未延伸フィルム
(3)基材1/接着層1/金属蒸着延伸フィルム
(4)透明蒸着延伸フィルム/接着層1/シーラントフィルム
(5)基材1/接着層1/基材2/接着層2/シーラントフィルム
(6)基材1/接着層1/金属蒸着延伸フィルム/接着層2/シーラントフィルム
(7)基材1/接着層1/透明蒸着延伸フィルム/接着層2/シーラントフィルム
(8)基材1/接着層1/金属層/接着層2/シーラントフィルム
(9)基材1/接着層1/基材2/接着層2/金属層/接着層3/シーラントフィルム
(10)基材1/接着層1/金属層/接着層2/基材2/接着層3/シーラントフィルム
等が挙げられるがこれに限定されない。
本発明の包装材は、本発明の積層体を袋状に成型してなる。製袋方法としては、本発明の積層体を折り曲げるか、あるいは重ねあわせてその内層の面(シーラントフィルムの面)を対向させ、その周辺端部を、例えば、側面シール型、二方シール型、三方シール型、四方シール型、封筒貼りシール型、合掌貼りシール型、ひだ付シール型、平底シール型、角底シール型、ガゼット型、その他のヒートシール型等の形態によりヒートシールする方法が挙げられる。本発明の包装材は内容物や使用環境、使用形態に応じて種々の形態をとり得る。自立性包装材(スタンディングパウチ)等も可能である。ヒートシールの方法としては、バーシール、回転ロールシール、ベルトシール、インパルスシール、高周波シール、超音波シール等の公知の方法で行うことができる。易開封処理や再封性手段が設けられていてもよい。
(ポリイソシアネート組成物(X-1))
撹拌機、温度計、窒素ガス導入管を備えたフラスコに、4,4-ジフェニルメタンジイソシアネート(以下、「MDI」と略記する):40.2部と、ヘキサメチレンジイソシアネートヌレート体(以下、「HDIヌレート」と略記する):10.0部とを反応容器内に仕込み、窒素ガス下で攪拌し、60℃まで加熱した。このフラスコに、さらに数平均分子量1000の2官能のポリプロピレングリコール(以下、「PPG」と略記する。):37.9部と、2,2,4-トリメチル-1,3-ペンタンジオール:2.0部とを混合して数回に分けて滴下し、80℃で5~6時間攪拌してウレタン化反応させることにより、ポリイソシアネートを得た。得られたポリイソシアネートを、カルボジイミド変性イソシアネート:10.0部と混合し、ポリイソシアネート組成物(X-1)を得た。
表1~3に示す配合で、ポリオール組成物(Y-1)~(Y-13)、(Y’-1)~(Y’-3)を調整した。表中の化合物は以下の通りである。
ポリオール(B1-1-1):アクトコールD-1000(三井化学社製、数平均分子量1000、2官能のポリプロピレンポリオール)
ポリオール(B1-1-2):アクトコールT-1000(三井化学社製、数平均分子量1000、3官能のポリプロピレンポリオール)
ポリオール(B1-1-3):アクトコールD-400(三井化学社製、数平均分子量400、2官能のポリプロピレンポリオール)
ポリオール(B1):D-4000(三井化学社製、数平均分子量4000、2官能のポリプロピレンポリオール)
ポリオール(B1-2):サンニックスHD-402(三洋化成工業社製、数平均分子量600、4官能のポリプロピレンポリオール)
ポリオール(B2):ひまし油
ポリオール(B3):クラレポリオールF-510(トリメチロールプロパン、3-メチル-1,5-ペンタンジオール、アジピン酸からなる重量平均分子量500のポリエステルトリオール)
化合物(C-1):ジメチロールプロピオン酸
化合物(C-2):ジメチロールブタン酸
ポリアミン(D1):ジェファーミン T-403(Huntsman社製、ポリオキシプロピレントリアミン、Mw=400、アミン価=355mgKOH/g)
ポリアミン(D2):モノエタノールアミン
ポリアミン(D3):ジエチルアミン
触媒(E1-1):BiCAT8(Shepherd社製、ネオデカン酸ビスマスとネオデカン酸亜鉛の混合物)
触媒(E1-2):ジラウリル酸ジブチルすず
触媒(E2):ε-カプロラクタム
KBM-403:信越シリコーン製、3-グリシドキシプロピルトリメトキシシラン
KBE-903:信越シリコーン製、3-アミノプロピルトリエトキシシラン
レベリング剤:サーフィノール420(EVONIK社製、アセチレン系ジアルコールのポリエーテル化物)
(ラミネート強度 OPP/VMCPP)
OPPフィルム(東洋紡社製、P2161)に加温したポリイソシアネート組成物(X)を、VMCPPフィルム(東レフィルム加工社製、2703)に加温したポリオール組成物(Y)を塗布し、OPPフィルムとVMCPPフィルムとをニップロール(50℃)で圧着し、25℃で24時間エージングしてOPP/接着層/VMCPPの積層体1を得た。ポリイソシアネート組成物(X)、ポリオール組成物(Y)の塗布量(g/m2)は表4、5に示す通りである。
5:1.5N/15mm以上
4:1.0N/15mm以上1.5N/15mm未満
3:0.5N/15mm以上1.0N/15mm未満
2:0.2N/15mm以上0.5N/15mm未満
1:0.2N/15mm未満
OPPフィルム(東洋紡社製、P2161)に加温したポリイソシアネート組成物(X)を、CPPフィルム(東洋紡社製、P1128)に加温したポリオール組成物(Y)を塗布し、OPPフィルムとCPPフィルムとをニップロール(50℃)で圧着してOPP/接着層/CPPの積層体2を得た。ポリイソシアネート組成物(X)、ポリオール組成物(Y)の塗布量(g/m2)は表4、5に示す通りである。積層体1と同様にしてラミネート強度を測定、評価し、結果を表4、5にまとめた。
コロナ処理PETフィルム(厚さ12μm)にポリイソシアネート組成物(X)を、VMCPPフィルム(厚さ25μm)にポリオール組成物(Y)を使用し、100、150、200、250m/minの加工速度でそれぞれ貼り合わせた。ポリイソシアネート組成物(X)、ポリオール組成物(Y)の塗布量(g/m2)は表4、5に示す通りである。25℃、24時間エージングした後、積層体に残存している気泡の有無を確認し、気泡が残存していない加工速度域を調べた。以下の5段階評価で評価し、結果を表4、5にまとめた。
5:100~250m/minで気泡残存なし
4:100~200m/minで気泡残存なし
3:100~150m/minで気泡残存なし
2:100m/minで気泡残存なし
1:100m/minで気泡残存あり
Claims (12)
- ポリイソシアネート組成物(X)と、ポリオール組成物(Y)と、を含み、
前記ポリイソシアネート組成物(X)はポリイソシアネート化合物(A)を含み、
前記ポリオール組成物(Y)はポリオール(B)と、2,2-ジメチロール酢酸、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸、2,2-ジメチロールペンタン酸からなる群から選ばれる少なくとも一種である化合物(C)と、NH2基またはNHR基(Rは官能基を有していてもよいアルキル基またはアリール基)から選ばれる基を複数有するポリアミン(D)とを含むことを特徴とする、2液硬化型接着剤。 - 前記ポリオール組成物(Y)のアミン価が20~70mgKOH/gである請求項1に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、ポリエーテルポリオール(B1)または植物油ポリオール(B2)の少なくとも一種を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、数平均分子量が130以上3000以下のポリエーテルジオール(B1-1)を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、3官能以上のポリエーテルポリオール(B1-2)を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、ポリエステルポリオール(B3)を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリエステルポリオール(B3)が、多価カルボン酸と多価アルコールとを含む組成物の反応生成物であって、前記多価カルボン酸に占める脂肪族多価カルボン酸の配合量が80質量%以上であり、前記多価アルコールに占める脂肪族多価アルコールの配合量が80質量%以上である請求項6に記載の2液硬化型接着剤。
- 前記ポリオール組成物(Y)が、ウレタン化触媒(E)を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリオール組成物(Y)に占める前記化合物(C)の配合量が0.1質量%以上10質量%以下である請求項1に記載の2液硬化型接着剤。
- 第1の基材と、第2の基材と、前記第1の基材と前記第2の基材とを貼り合せる接着層とを含み、前記接着層が請求項1~9のいずれか一項に記載の接着剤の硬化塗膜であることを特徴とする積層体。
- 第一の基材にポリイソシアネート化合物(A)を含むポリイソシアネート組成物(X)を塗布する工程と、
第二の基材にポリオール(B)と、2,2-ジメチロール酢酸、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸、2,2-ジメチロールペンタン酸からなる群から選ばれる少なくとも一種である化合物(C)と、NH2基またはNHR基(Rは官能基を有していてもよいアルキル基またはアリール基)から選ばれる基を複数有するポリアミン(D)とを含むポリオール組成物(Y)を塗布する工程と、
前記第一の基材と前記第二の基材とを、前記ポリイソシアネート組成物(X)と前記ポリオール組成物(Y)とが接触するように貼り合わせる工程とを含む積層体の製造方法。 - 請求項10に記載の積層体からなる包装材。
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