JP6512256B2 - 2液硬化型ラミネート接着剤、その硬化物、積層フィルムの製造方法、及び2液硬化型ラミネート接着剤用アミン溶液 - Google Patents
2液硬化型ラミネート接着剤、その硬化物、積層フィルムの製造方法、及び2液硬化型ラミネート接着剤用アミン溶液 Download PDFInfo
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- JP6512256B2 JP6512256B2 JP2017195966A JP2017195966A JP6512256B2 JP 6512256 B2 JP6512256 B2 JP 6512256B2 JP 2017195966 A JP2017195966 A JP 2017195966A JP 2017195966 A JP2017195966 A JP 2017195966A JP 6512256 B2 JP6512256 B2 JP 6512256B2
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- Prior art keywords
- laminating adhesive
- component curable
- polyol
- curable laminating
- propanediol
- Prior art date
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- 239000012939 laminating adhesive Substances 0.000 title claims description 34
- 150000001412 amines Chemical class 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 5
- 229920005989 resin Polymers 0.000 claims description 63
- 239000011347 resin Substances 0.000 claims description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 44
- -1 aliphatic polyol Chemical class 0.000 claims description 44
- 229920002396 Polyurea Polymers 0.000 claims description 42
- 229920002635 polyurethane Polymers 0.000 claims description 42
- 239000004814 polyurethane Substances 0.000 claims description 42
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 41
- 229920005862 polyol Polymers 0.000 claims description 41
- 239000000853 adhesive Substances 0.000 claims description 40
- 230000001070 adhesive effect Effects 0.000 claims description 39
- 150000003077 polyols Chemical class 0.000 claims description 32
- 239000004593 Epoxy Substances 0.000 claims description 27
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 24
- 229920000570 polyether Polymers 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 21
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 20
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 18
- 239000012948 isocyanate Substances 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 229920005906 polyester polyol Polymers 0.000 claims description 14
- 239000002985 plastic film Substances 0.000 claims description 13
- 229920006255 plastic film Polymers 0.000 claims description 13
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000008064 anhydrides Chemical class 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- 229940035437 1,3-propanediol Drugs 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 6
- 235000013772 propylene glycol Nutrition 0.000 claims description 6
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 5
- 238000003475 lamination Methods 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims description 4
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 4
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 4
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical group CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
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- 239000004707 linear low-density polyethylene Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 16
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- 238000001723 curing Methods 0.000 description 14
- 150000002513 isocyanates Chemical class 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 125000005442 diisocyanate group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 10
- 229920001228 polyisocyanate Polymers 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000005001 laminate film Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
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- 238000004448 titration Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
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- 229920001451 polypropylene glycol Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000004806 packaging method and process Methods 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- 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 5
- 239000002253 acid Substances 0.000 description 5
- 235000019437 butane-1,3-diol Nutrition 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920006284 nylon film Polymers 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 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 5
- 229920002799 BoPET Polymers 0.000 description 4
- 239000012790 adhesive layer 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
- 238000004132 cross linking Methods 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
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- 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 3
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229930185053 grandol Natural products 0.000 description 1
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- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- XGFDHKJUZCCPKQ-UHFFFAOYSA-N nonadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCO XGFDHKJUZCCPKQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000005026 oriented polypropylene Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000009517 secondary packaging Methods 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 230000005641 tunneling Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/02—Polyureas
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Description
前記ポリウレタンポリウレア樹脂(A)の反応成分はポリオール成分(α)、多価イソシアネート化合物(β)及びアミン化合物(Y)であり、前記ポリオール成分(α)が、(1)〜(4)から選ばれる少なくとも1つのポリオールである2液硬化型ラミネート接着剤に関する。
(1)ポリオキシアルキレングリコールであるポリエーテルポリオール(α1)
(2)エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、2−メチル−1,3プロパンジオール、2−エチル−2ブチル−1,3プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ネオペンチルグリコール、ペンタンジオール、3−メチル−1,5ペンタンジオール、ヘキサンジオール、オクタンジオール、又は1,4−ブタンジオールであるグリコール化合物(α’)
(3)前記グリコール化合物(α’)を多価カルボン酸又はその無水物(α2−1)とをエステル化反応させて得られるポリエステルポリオール(α2)
(4)前記ポリエーテルポリオール(α1)と、前記グリコール化合物(α’)と多価カルボン酸又はその無水物(α2−1)とをエステル化反応させて得られるポリエステルポリオール(α3)
[アミン価滴定方法]
所定量のポリウレタンポリウレア樹脂(A)にクリスタルバイオレット指示薬を加え、これを0.1mol/Lの過塩素酸(HClO4)酢酸溶液で青紫色から青色へ変化(赤みが消えた点)を終点として滴定する。同様にして試験も実施し、下記(式1)によって算出される値である。
アミン価(KOHmg)=56.1×[(Vs−Vb)/W]×0.1×[F20/1+W:滴定に使用したポリウレタンポリウレア樹脂(A)の質量(g)
0.0011(t−20)]
Vs:滴定に要した0.1mol/Lの過塩素酸(HClO4)酢酸溶液の滴定量
F20:0.1mol/Lの過塩素酸(HClO4)酢酸溶液の20℃における力価
t:滴定時の0.1mol/Lの過塩素酸(HClO4)酢酸溶液の温度
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
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)
もちろんその他の用途、例えば防壁材、屋根材、太陽電池パネル材、電池用包装材、窓材、屋外フローリング材、照明保護材、自動車部材、看板、ステッカー等の屋外産業用途、射出成形同時加飾方法等に使用する加飾用シート等として、好適に使用することができる。
攪拌機、温度計、環流冷却器および窒素ガス導入管を備えた4つ口フラスコに、分子量約3000のポリプロピレングリコール(三井化学社製 アクトコール「PPG3000」、分子量3024(水酸基価37.1mgKOH/g、官能基数2としての計算値))と、1,3−ブタンジオールの混合物(重量比=97/3)192.7質量部とイソフォロンジイソシアネート47.29質量部を仕込み、窒素気流下に90℃で5時間反応させ、遊離イソシアネート価(イソシアネート基含有率)3.07質量%のプレポリマーを製造した後、これに酢酸エチル60質量部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン14.88質量部、シクロヘキシルアミン1.25質量部、酢酸エチル2.9質量部およびエタノール146.7質量部からなる混合物に、前記ウレタンプレポリマー溶液を添加し、45℃で5時間攪拌反応させて、ポリウレタンポリ尿素樹脂溶液Aを得た。得られたポリウレタンポリ尿素樹脂溶液Aは、樹脂固形分濃度が55質量%、樹脂のアミン価3.82mgKOH/g、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が800mPa・s(25℃)、樹脂固形分の重量平均分子量(Mw)が52,000であった。
実施例1の1,3-ブタンジオールを1,4-ブタンに変更した以外は同じ製造法で行った。得られたポリウレタンポリ尿素樹脂溶液Bとした。得られたポリウレタンポリ尿素樹脂溶液Bは、樹脂固形分濃度が55質量%、樹脂のアミン価3.82mgKOH/g、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が1,000mPa・s(25℃)、樹脂固形分の重量平均分子量(Mw)が53,000であった。
攪拌機、温度計、環流冷却器および窒素ガス導入管を備えた4つ口フラスコに、分子量約1000のポリプロピレングリコール(三井化学社製「アクトコール PPG1,000」、分子量1001(水酸基価112.0mgKOH/g、官能基数2としての計算値))と、分子量2015(水酸基価からの計算値)のポリプロピレングリコール(三井化学社製「アクトコール PPG2000」、分子量2015(水酸基価55.7mgKOH/g、官能基数2としての計算値))の混合物(重量比=95/5)185.2質量部とトルエンジイソシアネート62.92質量部を仕込み、窒素気流下に90℃で5時間反応させ、遊離イソシアネート価(イソシアネート基含有率)6.07質量%のプレポリマーを製造した後、これに酢酸エチル62.03質量部を加えてウレタンプレポリマーの均一溶液とした。次いで、2−(2−アミノエチルアミノ)エタノール24.12質量部、モノエタノールアミン0.2質量部、酢酸エチル4.9質量部およびエタノール156.0質量部からなる混合物に、前記ウレタンプレポリマー溶液を添加し、45℃で5時間攪拌反応させて、ポリウレタンポリ尿素樹脂溶液Cを得た。得られたポリウレタンポリ尿素樹脂溶液Cは、樹脂固形分濃度が55質量%、樹脂のアミン価23mgKOH/g、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が800mPa・s(25℃)、樹脂固形分の重量平均分子量(Mw)が32,000であった。
下記の方法にて接着剤及びラミネートフィルムを製造し、各種評価を行った。結果を表1〜表3に示す。
表1、表3の配合に従い、接着剤を製造した後、PETフィルム(東洋紡社製「E5100」厚さ12μm)に、塗布量が固形分3.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面と直鎖状低密度ポリエチレンフィルム(三井東セロ社製LLDPE「TUX−HC60μm」)と貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間のエージングを実施した。
表1、表3の配合に従い、接着剤を製造した後、ナイロン製フィルム(厚さ15μm)に、塗布量が固形分3.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面と直鎖状低密度ポリエチレンフィルム(三井東セロ社製LLDPE「TUX−HC60μm」)と貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間のエージングを実施した。
表2の配合に従い、各樹脂溶液とアミノシランカップリング剤とを配合して主剤成分を調整し、次いで、エポキシ化合物及び酢酸エチルを配合することによって接着剤を製造した後、印刷インキ(サンケミカル社製「Duralam PF」)で青、白の順にフレキソ印刷されたPETフィルム(東洋紡社製「E5100」厚さ12μm)に、塗布量が固形分3.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面と直鎖状低密度ポリエチレンフィルム(三井東セロ社製LLDPE「TUX−HC60μm」)と貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間のエージングを実施した。
表2の配合に従い、各樹脂溶液とアミノシランカップリング剤とを配合して主剤成分を調整し、次いで、エポキシ化合物及び酢酸エチルを配合することによって接着剤を製造した後、印刷インキ(サンケミカル社製「Duralam PF」)で青、白の順にフレキソ印刷されたナイロンフィルム(厚さ15μm)に、塗布量が固形分3.0g/m2程度となるように塗布し、ラミネーターでこのフィルムの塗布面と直鎖状低密度ポリエチレンフィルム(三井東セロ社製LLDPE「TUX−HC60μm」)と貼合し、ラミネートフィルムを作製した。このラミネートフィルムを40℃の恒温槽に3日間のエージングを実施した。
前記した各ラミネートフィルムから15mm幅で切り出したサンプルのピール強度を、雰囲気温度25℃で引張り試験機を用いて、剥離速度を300mm/分に設定し、T型の剥離方法で引張り試験による接着強度(N/15mm)を測定した。
前記した各ラミネートフィルムをLLDPEが内側になるように折り曲げ、1atm、180℃、1秒間でヒートシールして内容物の接触部分が200cm2となるパウチを作製し、食品疑似溶液内容物[食用酢:ミートソース:サラダ油(質量比)=1:1:1の溶液]の50mlを充填した。
充填したパウチを98℃の高温水で60分間浸漬し、取り出し、内容物を除去したパウチのラミネートフィルム部から15mm幅で切り出したサンプルのピール強度を、雰囲気温度25℃で引張り試験機を用いて、剥離速度を300mm/分に設定し、T型の剥離方法で測定した際の引張り試験による接着強度(N/15mm)を測定した。
エージング処理して得られたラミネートフィルムの状態を目視にて観察し、トンネリング等のラミネート外観が良好なものを「良好」とした。
ボイル処理後のパウチの外観を評価した。
○:デラミネーションなし
×:デラミネーションあり
なお、表1〜表3中に記載された各原料及び基材フィルムの詳細は以下のとおりである。
アミノシランカップリング剤:エボニック社製「Dynasylan AMEO」
ペンタエリスリトールポリグリシジルエーテル:ペンタエリスリトールのポリグリシジルエーテル(3〜4官能、エポキシ当量229g/eq.)
TMP系ポリグリシジルエーテル:トリメチロールプロパンのポリグリシジルエーテル(2〜3官能、エポキシ当量134g/eq.)
BPA系ポリグリシジルエーテル:ビスフェノールAのジグリシジルエーテル(DIC(株)製「EPICLON850」エポキシ当量188g/eq.)
ソルビトール系ポリグリシジルエーテル:ソルビトールのポリグリシジルエーテル(3〜4官能、エポキシ当量173g/eq.、粘度5,000mPa・s)
N,N,N’,N’−テトラグリシジル−1,3−ベンゼンジ(メタンアミン):三菱瓦斯化学社製「TETRAD−X」(粘度1600−3000mPa・s)
N,N,N’,N’−テトラキス(2,3−エポキシプロピル)シクロヘキサン−1,3−ジメチルアミン:三菱瓦斯化学社製「TETRAD−C」(粘度1600−3000mPa・s)
Ny:ナイロンフィルム(ユニチカ社製「エンブレムON」厚さ15μm)
PET:PETフィルム(東洋紡社製「E5100」厚さ12μm)
LLDPE:直鎖状低密度ポリエチレンフィルム(三井東セロ社製「TUX−HC」厚さ60μm)
Claims (8)
- 1級アミノ基を分子構造中に有するポリウレタンポリウレア樹脂(A)と、多官能エポキシ化合物(B)として鎖状脂肪族ポリオールのポリグリシジルエーテルとを必須成分とする2液硬化型ラミネート接着剤であって、
前記ポリウレタンポリウレア樹脂(A)の反応成分はポリオール成分(α)、多価イソシアネート化合物(β)及びアミン化合物(Y)であり、前記ポリオール成分(α)が、(1)、(3)または(4)から選ばれる少なくとも1つのポリオールであることを特徴とする2液硬化型ラミネート接着剤。
(1)ポリオキシアルキレングリコールであるポリエーテルポリオール(α1)
(3)(2)エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、2−メチル−1,3プロパンジオール、2−エチル−2ブチル−1,3プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ネオペンチルグリコール、ペンタンジオール、3−メチル−1,5ペンタンジオール、ヘキサンジオール、オクタンジオール、又は1,4−ブタンジオールであるグリコール化合物(α’)を多価カルボン酸又はその無水物(α2−1)とをエステル化反応させて得られるポリエステルポリオール(α2)
(4)前記ポリエーテルポリオール(α1)と、(2)エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、2−メチル−1,3プロパンジオール、2−エチル−2ブチル−1,3プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ネオペンチルグリコール、ペンタンジオール、3−メチル−1,5ペンタンジオール、ヘキサンジオール、オクタンジオール、又は1,4−ブタンジオールであるグリコール化合物(α’)と多価カルボン酸又はその無水物(α2−1)とをエステル化反応させて得られるポリエステルポリオール(α3) - 前記1級アミノ基を分子構造中に有するポリウレタンポリウレア樹脂(A)が、アミン価3.0〜30mgKOH/gの範囲である請求項1に記載の2液硬化型ラミネート接着剤。
- 前記1級アミノ基を分子構造中に有するポリウレタンポリウレア樹脂(A)が、ポリエーテルポリウレタンポリウレア樹脂である請求項1〜2に記載の2液硬化型ラミネート接着剤。
- 前記ポリエーテルポリウレタンポリウレア樹脂が、該樹脂中に存在するポリエーテル構造部位の原料の分子量が100〜3,500の範囲である請求項3に記載の2液硬化型ラミネート接着剤。
- 前記鎖状脂肪族ポリオールのポリグリシジルエーテルのエポキシ当量が100〜300g/当量の範囲にある請求項1〜4のいずれかに記載の2液硬化型ラミネート接着剤。
- アミノシランカップリング剤を含有する請求項1〜5のいずれかに記載の2液硬化型ラミネート接着剤。
- 請求項1〜6のいずれかに記載の2液硬化型ラミネート接着剤を硬化させてなる硬化物。
- 請求項1〜6のいずれかに記載の2液硬化型ラミネート接着剤を第一のプラスチックフィルムと第二のプラスチックフィルムの間に有することを特徴とする積層フィルム。
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JP6960422B2 (ja) * | 2019-01-29 | 2021-11-05 | 大日精化工業株式会社 | 接着剤組成物及び積層体 |
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