JP2007106797A - ラミネートフィルム用接着剤組成物 - Google Patents
ラミネートフィルム用接着剤組成物 Download PDFInfo
- Publication number
- JP2007106797A JP2007106797A JP2005296390A JP2005296390A JP2007106797A JP 2007106797 A JP2007106797 A JP 2007106797A JP 2005296390 A JP2005296390 A JP 2005296390A JP 2005296390 A JP2005296390 A JP 2005296390A JP 2007106797 A JP2007106797 A JP 2007106797A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane resin
- carbodiimide
- resin composition
- adhesive composition
- group
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 77
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 75
- 239000005001 laminate film Substances 0.000 title claims abstract description 52
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- -1 carbodiimide compound Chemical class 0.000 claims abstract description 126
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 64
- 239000011342 resin composition Substances 0.000 claims abstract description 58
- 229920005862 polyol Polymers 0.000 claims abstract description 35
- 150000003077 polyols Chemical class 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 33
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 24
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 17
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 17
- 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 15
- 230000002378 acidificating effect Effects 0.000 claims abstract description 15
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 19
- 238000004806 packaging method and process Methods 0.000 claims description 12
- 235000013305 food Nutrition 0.000 claims description 11
- 150000002009 diols Chemical class 0.000 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004945 emulsification Methods 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 12
- 238000009835 boiling Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 17
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000005025 cast polypropylene Substances 0.000 description 9
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000002216 antistatic agent Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000010835 comparative analysis Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 238000003851 corona treatment Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 229920000092 linear low density polyethylene Polymers 0.000 description 4
- 239000004707 linear low-density polyethylene Substances 0.000 description 4
- 239000002075 main ingredient Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 150000001450 anions Chemical group 0.000 description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 150000001768 cations Chemical group 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- XATSGKXHVKZFKL-UHFFFAOYSA-N cyclohexylmethylcyclohexane;methanediimine Chemical compound N=C=N.C1CCCCC1CC1CCCCC1 XATSGKXHVKZFKL-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 229920001684 low density polyethylene Polymers 0.000 description 3
- 239000004702 low-density polyethylene Substances 0.000 description 3
- FRVOOSTVCDXSRG-UHFFFAOYSA-N methanediimine;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=N.CC1=CC(=O)CC(C)(C)C1 FRVOOSTVCDXSRG-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- OJRJDENLRJHEJO-UHFFFAOYSA-N 2,4-diethylpentane-1,5-diol Chemical compound CCC(CO)CC(CC)CO OJRJDENLRJHEJO-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-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
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 125000005263 alkylenediamine group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- HLOWLJPNVWXOKQ-UHFFFAOYSA-N benzylbenzene;methanediimine Chemical compound N=C=N.C=1C=CC=CC=1CC1=CC=CC=C1 HLOWLJPNVWXOKQ-UHFFFAOYSA-N 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
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- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
【解決手段】カルボジイミド基と反応し得る官能基を有する水溶性又は水分散型のポリウレタン樹脂組成物を主剤とし、カルボジイミド化合物を硬化剤とし、ポリウレタン樹脂組成物中の該官能基の100当量に対して、カルボジイミド化合物のカルボジイミド基が15〜130当量であり、該ポリウレタン樹脂組成物は、分子量200〜3000のポリオール成分、ポリイソシアネート成分、ジメチロールブタン酸、酸性基中和剤及び末端停止剤から得られる分子量が3000〜8000のポリウレタン樹脂が、第三ブタノールに溶解されているものであることを特徴とするラミネートフィルム用接着剤組成物。
【選択図】なし
Description
本発明のポリウレタン樹脂組成物は、その他、イ)ポリオール成分(a)及びポリイソシアネート成分(b)、ジメチロールブタン酸(c)、酸性基中和剤(d)、末端停止剤(e)及び溶媒としての第三ブタノールを一括で加えて反応を行う方法、あるいはロ)ポリオール成分(a)にポリイソシアネート成分(b)、ジメチロールブタン酸(c)、酸性基中和剤(d)、末端停止剤(e)及び溶媒としての第三ブタノールを順次加えて反応を行う方法によっても得られる。
カルボジイミド化合物(B)は、カルボジイミド基を有する化合物であれば特に制限されないが、例えば、有機ジイソシアネートを、ホスホレン化合物、金属カルボニル錯体化合物及びリン酸エステル等のようにカルボジイミド化を促進する触媒の存在下に反応させることにより得られるイソシアネート末端カルボジイミド化合物を用いることができる。カルボジイミド化合物(B)としては、さらに該イソシアネート末端カルボジイミド化合物に親水性セグメント化合物を反応させた水性カルボジイミド化合物も用いることができる。
尚、本発明でいう「水性」という語は、本発明に係るカルボジイミド化合物(B)が、水溶性或いは自己乳化性、その他の水と均一になじむ性質を有していることを意味するものである。
カルボジイミド化合物(B)を水に溶解又は分散させる際には、好ましくは固形分が5〜80質量%の範囲となるようにする。
また、ポリウレタン樹脂組成物(A)及びカルボジイミド化合物(B)の使用量は、ポリウレタン樹脂組成物(A)の固形分100質量部に対し、カルボジイミド化合物(B)が固形分で1〜100質量部となる範囲から、上記当量比を満たすように選択することが好ましい。
上記のうち、OPP/CPP、PET/CPP、OPP/LLDPE、PET/LLDPE、ONY/LLDPE、PET/Al/CPP等のフィルムの組み合わせは、特に食品包装用として広く用いられている。
フィルムの厚みは、ラミネートフィルムの使用用途等に応じて適宜選択することができるが、好ましくは5〜100μmである。
3−メチル−1,5−ペンタンジオールとアジピン酸から得た数平均分子量2000のポリエステルポリオール0.20モル、イソホロンジイソシアネート1.00モル及び1,4−ブタンジオール0.49モルを反応フラスコに仕込み、窒素気流中で、100℃で2時間反応させてポリウレタンプレポリマーを得た。次に、このポリウレタンプレポリマー656gを第三ブタノール250gに溶解し、ジメチロールブタン酸0.18モル及びN−メチルモルフォリン0.25モルを加えて60〜70℃で2時間反応させた後、1,4−ブタンジオール0.49モルを加えて60〜70℃でイソシアネート基が消失するまで攪拌し、末端水酸基のポリウレタン樹脂組成物No.1を得た。得られたポリウレタン樹脂組成物No.1は、ウレタン結合濃度2.75eq/kg、粘度71000mPa・s/25℃、平均分子量が5200、固形分は70.6%であった。
3−メチル−1,5−ペンタンジオールとアジピン酸から得た数平均分子量2000のポリエステルポリオール0.20モル、イソホロンジイソシアネート1.00モル及び1,4−ブタンジオール0.49モルを反応フラスコに仕込み、窒素気流中で、100℃で2時間反応させてポリウレタンプレポリマーを得た。次に、このポリウレタンプレポリマー656gを第三ブタノール250gに溶解し、ジメチロールブタン酸0.18モル及びN−エチルモルフォリン0.25モルを加えて60〜70℃で2時間反応させた後、1,4−ブタンジオール0.49モルを加えて60〜70℃でイソシアネート基が消失するまで攪拌し、ポリウレタン樹脂組成物No.2を得た。得られたポリウレタン樹脂組成物No.2は、ウレタン結合濃度2.74eq/kg、粘度50000mPa・s/25℃、平均分子量が5200、固形分は68.2%であった。
3−メチル−1,5−ペンタンジオールとアジピン酸から得た数平均分子量2000のポリエステルポリオール0.20モル、イソホロンジイソシアネート1.00モル及び1,4−ブタンジオール0.49モルを反応フラスコに仕込み、窒素気流中で、100℃で2時間反応させてポリウレタンプレポリマーを得た。次に、このポリウレタンプレポリマー656gを第三ブタノール250gに溶解し、ジメチロールブタン酸0.18モル及びN−エチルモルフォリン0.25モルを加えて60〜70℃で2時間反応させた後、トリメチロールプロパン0.49モルを加えて60〜70℃でイソシアネート基が消失するまで攪拌し、ポリウレタン樹脂組成物No.3を得た。得られたポリウレタン樹脂組成物No.3は、ウレタン結合濃度2.77eq/kg、粘度100000mPa・s/25℃、平均分子量が5200、固形分は69.8%であった。
上記の製造例で得られたポリウレタン樹脂組成物No.1〜No.3の42.5gそれぞれを、水57.5gに分散させて水分散型ポリウレタン樹脂組成物No.1〜No.3とした。
主剤としての該水分散型ポリウレタン樹脂組成物に、硬化剤として下記表1に記載のカルボジイミド化合物を配合して、ラミネートフィルム用接着剤組成物をそれぞれ得た。
尚、主剤(水分散型ポリウレタン樹脂組成物)100gに対する硬化剤(カルボジイミド化合物)の配合量は表1に記載した通りである。また、表1におけるラミネートフィルム用接着剤組成物の配合比は、水分散型ポリウレタン樹脂組成物中のカルボジイミド基と反応し得る官能基の100当量に対するカルボジイミド化合物のカルボジイミド基の当量を示す。
これらのラミネートフィルム用接着剤組成物について、下記評価例1及び3では、ボイル試験後の接着性評価を行い、下記評価例2では、レトルト試験後の接着性評価を行った。
コロナ放電処理した厚さ20μmの延伸ポリプロピレンフィルム(OPP)の処理面に、バーコーターを用いてラミネートフィルム用接着剤組成物を膜厚5μmに塗工後、ヘアドライヤーを用いて塗工面を10秒乾燥した。これにコロナ放電処理した厚さ40μmの未延伸キャストポリプロピレンフィルム(CPP)の処理面を重ねた後、常温にてロールで圧着した。これを40℃で2日間放置して、接着サンプルとしてのラミネートフィルムを得た。得られた接着サンプルについて、ボイル試験(95℃熱水中、30分)を行った後、180°T型剥離試験(試験片:200mm×15mm、引張速度:300mm/分、測定雰囲気:25℃×50%RH)により接着強度を測定した。それらの結果を表1に示す。尚、表1には、これらの結果と共に、ボイル試験をしていない接着サンプルの強度(初期強度)も示す。
また、T型剥離試験時に接着サンプルの剥離状態を目視観察し、ボイル試験及び初期のいずれの測定においても材料破壊したものを○、いずれかの測定において未延伸基材伸び剥離が認められたものを△、いずれかの測定において界面剥離が認められたものを×として評価した。これらの結果を表1に示す。表1に示す通り、比較評価例1−1〜比較評価例1−4の評価結果は、いずれも×であった。これは、比較評価例1−1〜1−4いずれにおいても、初期強度の測定で接着界面剥離が認められたためである。さらに、比較評価例1−1においては、ボイル試験で接着剤の部分が界面剥離を起こしたため、その後の接着強度の測定は実施できなかった。
但し、表1において、フィルムの名称及び厚さは以下の通りである。
OPP:延伸ポリプロピレン、厚さ20μm
PET:延伸ポリエチレンテレフタレート、厚さ12μm
ONY:延伸ナイロン、厚さ15μm
CPP:未延伸キャストポリプロピレン、厚さ40μm
LLDPE:未延伸低密度ポリエチレン、厚さ50μm
・V−02:「カルボジライトV−02」日清紡(株)製、NCN当量590、固形分40%
・V−02−L2:「カルボジライトV−02−L2」日清紡(株)製、NCN当量385、固形分40%
・E−02:「カルボジライトE−02(エマルジョンタイプ)」日清紡(株)製、NCN当量445、固形分40%
・EX−614B:「デナコールEX−614B」ナガセケムテックス(株)製、エポキシ当量170、固形分100%
・WS−700:「エポクロスWS−700」(株)日本触媒製、オキサゾリン当量220、固形分25%
上記評価例1と同様の方法で、接着サンプルとしてのラミネートフィルムを作製した。得られた接着サンプルについてレトルト試験(120℃水蒸気中、30分)を行った。その後180°T型剥離試験(試験片:200mm×15mm、引張速度:300mm/分、測定雰囲気:25℃×50%RH)により接着強度を測定した。それらの結果を表2に示す。尚、表2には、これらの結果と共に、レトルト試験をしていない接着サンプルの強度(初期強度)も示す。
評価例1と同様の方法でラミネートフィルムを作製した。但し、ラミネートフィルムは、サイズが12cm×14cmの袋とした。この袋に、内容物として水と酢と油との混合物(重量比:水/酢/油=10/1/1)を充填した。内容物を充填した袋を沸騰水中で30分間の条件で煮沸高温殺菌(ボイル試験)した後、袋の外観を目視観察した。剥離状態が認められず外観が良好なものを○、剥離状態が観察されたものは×とした。結果を〔表3〕に示す。
Claims (7)
- カルボジイミド基と反応し得る官能基を有する水溶性又は水分散型のポリウレタン樹脂組成物(A)を主剤とし、カルボジイミド化合物(B)を硬化剤としたラミネートフィルム用接着剤組成物であり、該ポリウレタン樹脂組成物(A)中のカルボジイミド基と反応し得る官能基の100当量に対して、該カルボジイミド化合物(B)のカルボジイミド基が15〜130当量の範囲であり、該ポリウレタン樹脂組成物(A)は、分子量200〜3000のポリオール成分(a)、ポリイソシアネート成分(b)、ジメチロールブタン酸(c)、酸性基中和剤(d)及び末端停止剤(e)から得られる分子量が3000〜8000のポリウレタン樹脂が、第三ブタノールに溶解されているポリウレタン樹脂組成物であることを特徴とするラミネートフィルム用接着剤組成物。
- 上記ポリオール成分(a)のジオール成分が、ジカルボン酸及び低分子ジオールから得られるポリエステルジオールである請求項1記載のラミネートフィルム用接着剤組成物。
- 上記低分子ジオールが、3−メチル−1,5−ペンタンジオールである請求項2記載のラミネートフィルム用接着剤組成物。
- 上記ポリイソシアネート成分(b)のジイソシアネートが、脂環式ジイソシアネート類である請求項1〜3のいずれかに記載のラミネートフィルム用接着剤組成物。
- 上記カルボジイミド化合物(B)が、分子中に親水性基が導入された水性カルボジイミド化合物であり、該水性カルボジイミド化合物を自己乳化法により水に溶解させて上記硬化剤として用いる請求項1〜4のいずれかに記載のラミネートフィルム用接着剤組成物。
- 上記ポリウレタン樹脂組成物(A)中のカルボジイミド基と反応し得る官能基の100当量に対して、上記カルボジイミド化合物(B)のカルボジイミド基が50〜100当量の範囲である請求項1〜5のいずれかに記載のラミネートフィルム用接着剤組成物。
- 食品包装用途のラミネートフィルムに用いる請求項1〜6のいずれかに記載のラミネートフィルム用接着剤組成物。
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WO2019131414A1 (ja) * | 2017-12-26 | 2019-07-04 | Dic株式会社 | 水性樹脂組成物、それを用いた積層体及び物品 |
CN111511836A (zh) * | 2017-12-26 | 2020-08-07 | Dic株式会社 | 水性树脂组合物、使用了该组合物的层叠体和物品 |
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