JP2022536966A - レトルト接着剤組成物 - Google Patents
レトルト接着剤組成物 Download PDFInfo
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- JP2022536966A JP2022536966A JP2021575386A JP2021575386A JP2022536966A JP 2022536966 A JP2022536966 A JP 2022536966A JP 2021575386 A JP2021575386 A JP 2021575386A JP 2021575386 A JP2021575386 A JP 2021575386A JP 2022536966 A JP2022536966 A JP 2022536966A
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- Japan
- Prior art keywords
- component
- isocyanate
- adhesive
- layer
- polyol
- 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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- 239000000853 adhesive Substances 0.000 title claims abstract description 157
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 157
- 239000000203 mixture Substances 0.000 title claims abstract description 135
- -1 isocyanate compound Chemical class 0.000 claims abstract description 115
- 239000012948 isocyanate Substances 0.000 claims abstract description 95
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 43
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 31
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 27
- 239000010452 phosphate Substances 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 18
- 239000004814 polyurethane Substances 0.000 claims abstract description 11
- 229920002635 polyurethane Polymers 0.000 claims abstract description 11
- 229920005862 polyol Polymers 0.000 claims description 107
- 150000003077 polyols Chemical class 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 18
- 229920000570 polyether Polymers 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- 239000004417 polycarbonate Substances 0.000 claims description 6
- 229920000515 polycarbonate Polymers 0.000 claims description 6
- 229920003232 aliphatic polyester Polymers 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 239000004632 polycaprolactone Substances 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 description 47
- 229920001228 polyisocyanate Polymers 0.000 description 47
- 239000010408 film Substances 0.000 description 45
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 43
- 150000001875 compounds Chemical class 0.000 description 39
- 239000000758 substrate Substances 0.000 description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 239000002243 precursor Substances 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000003822 epoxy resin Substances 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000012939 laminating adhesive Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 235000013305 food Nutrition 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 239000011888 foil Substances 0.000 description 10
- 229920000137 polyphosphoric acid Polymers 0.000 description 10
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 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 8
- 230000033228 biological regulation Effects 0.000 description 8
- 239000005025 cast polypropylene Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 235000011007 phosphoric acid Nutrition 0.000 description 6
- 229920001748 polybutylene Polymers 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 230000001105 regulatory effect Effects 0.000 description 6
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- 239000002318 adhesion promoter Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009459 flexible packaging Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 150000007519 polyprotic acids Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 150000004072 triols Chemical class 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 238000005102 attenuated total reflection Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- YHTLGFCVBKENTE-UHFFFAOYSA-N 4-methyloxan-2-one Chemical compound CC1CCOC(=O)C1 YHTLGFCVBKENTE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IXQBIOPGDNZYNA-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C IXQBIOPGDNZYNA-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000006087 Silane Coupling Agent 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000005001 laminate film Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- 235000015067 sauces Nutrition 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- 229920001169 thermoplastic Polymers 0.000 description 2
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- 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 2
- 239000013638 trimer Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 description 1
- VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
- DWIHAOZQQZSSBB-UHFFFAOYSA-N 1-isocyanato-1-(2-isocyanatopropyl)cyclohexane Chemical compound O=C=NC(C)CC1(N=C=O)CCCCC1 DWIHAOZQQZSSBB-UHFFFAOYSA-N 0.000 description 1
- FPWRWTXOOZSCTB-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CC(N=C=O)CCC1CC1C(N=C=O)CCCC1 FPWRWTXOOZSCTB-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
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- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- HSFQKNCRVXWMPS-UHFFFAOYSA-N 3-[2-aminoethyl-methoxy-[(2-methylpropan-2-yl)oxy]silyl]propan-1-amine Chemical compound NCC[Si](OC(C)(C)C)(OC)CCCN HSFQKNCRVXWMPS-UHFFFAOYSA-N 0.000 description 1
- ZDZYGYFHTPFREM-UHFFFAOYSA-N 3-[3-aminopropyl(dimethoxy)silyl]oxypropan-1-amine Chemical compound NCCC[Si](OC)(OC)OCCCN ZDZYGYFHTPFREM-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- TUZMHNASXCXMBO-UHFFFAOYSA-N 3-methylpentane-2,2-diol Chemical compound CCC(C)C(C)(O)O TUZMHNASXCXMBO-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
実施例で使用される接着剤配合物の成分は、表IIに記載されており、接着剤配合物は、以下の手順に従って調製される:
リン酸エステル化合物を調製するための一般手順
1リットル(L)のマルチネック丸底フラスコをオーブンで乾燥させ、乾燥窒素(N2)で30分間フラッシュし、次に150グラム(g)のVORANOL(商標)CP450ポリエーテルポリオールを充填し、分当たり70ミリリットル(mL/分)のN2掃引下に置いた。シリンジに、4 gの115%のPolyphosphoric20酸(PPA)を充填した。PPAを、強く撹拌しながらポリエーテルポリオールに滴下した。最小限の温度上昇が観察された。反応器の内容物を100℃まで1時間加熱し、次に45℃まで冷却した。次に、40 gの酢酸エチルを反応器に添加し、続いて50 gのISONATE(商標)125Mジイソシアネートをゆっくりと添加した。氷バッチを適用して顕著な発熱を制御して、反応ポットを75℃未満に保持し、黄色25から琥珀色の発色を観察した。次に、反応器を65℃で1時間維持し、その時点で内容物を冷却して包装した。生成物は、以下の特性を有した:固形分76.0%、112 mg KOH/gのヒドロキシル価(OHN)、19.0 mg KOH/gの酸価(AV)、および1,665ミリパスカル-秒(mPa・s)の25℃での粘度。
本発明の実施例1および本発明の実施例2のイソシアネート反応性成分を調製するための適切な成分を、表IIに記載する。試料調製の典型的な例として本発明の実施例1のイソシアネート成分を使用して、約450 gのADCOTE(商標)577および約50 gのMOR-FREE(商標)C33をガラス反応器に充填する。反応器を約40℃まで加熱し、生じた混合物を40℃で約30分間撹拌する。次に、生じた試料混合物を包装し、後で使用するために倉庫に置く。
本発明の実施例1および本発明の実施例2のイソシアネート反応性成分を調製するための適切な成分を、表IIに記載する。試料調製の典型的な例として実施例1のイソシアネート反応性成分を使用して、約400 gのVORANOL(商標)CP450、約40 gのPOLYG(商標)30-112、および約360 gのリン酸エステル化合物をガラス反応器に充填する。反応器を約40℃まで加熱し、生じた混合物を40℃で約30分間撹拌する。次に、生じた試料混合物を包装し、後で使用するために倉庫に置く。
イソシアネート反応性成分、イソシアネート成分、および溶剤を含む、接着剤配合物を調製するための適切な成分を、表IIに記載する。接着剤配合試料調製の典型的な例として本発明の実施例1の接着剤を使用して、約1,000 gのイソシアネート成分(成分A)、約160 gのイソシアネート反応性成分(成分B)、および約1,460 gの酢酸エチルをプラスチック容器に充填する。材料を、機械的ミキサを使用して室温(約25℃)で30分間混合して、本発明の実施例1の配合接着剤を得る。
ラミネートを調製するための一般手順
表IIIは、上の表IIに記載の接着剤を使用してラミネートおよびラミネート試料を調製するために実施例で使用される様々なフィルムを記載している。溶剤系接着剤に基づくラミネートは、Nordmeccanica Labo Combi 400パイロットコーターを介して室温(約25℃)で生成した。ポリマーフィルムは、ラミネーションの前にコロナ処理し、アルミニウム(Al)ホイルは、コロナ処理せずに使用した。各ラミネートのコート重量は、平方メートル当たり約4.9グラム(g/m2)に維持した。調製したラミネートを、その後、制御された環境(例えば、25℃および50℃で50%の相対湿度)で硬化させた。
結合強度測定
幅15 mmおよび長さ1インチ (25.4 mm)のストリップに切断したラミネート試料に90°T型剥離試験を実行し、10インチ/分(254 mm/分)の速度で、50ニュートン(N)荷重セルを備えたThwing Albert(商標)QC-3A剥離試験機で1インチ(25.4 mm)のストリップ上で引張した。3つの別個の試料ストリップを試験し、3つのストリップの結果値を平均化した。ラミネート中の2つのフィルムが分離(剥離)するときの、引張中の力の平均を記録した。フィルムのうちの1つが伸張または破断した場合、最大の力または破断時の力を記録した。不良モード(FM)または不良のモード(MOF)を、以下の次の名称に従って記録した。
ATRを使用して、ホイル//CPP構造の本発明の接着剤および比較接着剤の硬化を監視し、イソシアネートのピークがATRスペクトルから消えたときに、使用した各接着剤の硬化時間を決定した。
ラミネートは、上記のようにPrelam//CPPから作製した。一方の層のCPPフィルムが他方の層のCPPフィルムと接触するように、ラミネートの9インチ×12インチ(23 cm×30.5 cm)シートのうちの1つを折り畳んで、約9インチ×6インチ(23 cm×15.3 cm)の二重層を得た。折り畳んだラミネートの縁をペーパーカッターでトリミングして、約5インチ×7インチ(12.7 cm×17.8 cm)の折り畳んだ片を得た。折り畳んだ片の2つの長辺と1つの短辺とを縁でヒートシールして、4インチ×6インチ(10.2 cm×15.2 cm)の内部サイズを有する完成パウチを得た。400°F(204℃)で1秒間(秒)、平方インチ当たり40ポンド(psi)(276キロパスカル[kPa])の水圧で、ヒートシールを行った。各試験のために、2つまたは3つのパウチを作製した。
レトルト性能試験
上記のように調製したパウチに、開放縁を通じて100ミリリットル(mL)±5 mLの蒸留水(DI水)または1:1:1のソース(ケチャップ、酢、および植物油の等重量部のブレンド)を充填した。試験中にヒートシール不良を引き起こし得るので、ヒートシール領域上への充填物の跳ね上がりを回避した。充填後、パウチの内側への空気の封じ込めを最小限に抑える様式で、パウチの上部を密封した。試験中にパウチの漏れを引き起こすであろう密封部に傷がないことを確実にするために、パウチの4つの側面すべてについて密封が完全であることを検査した。少しでも欠陥のあるパウチは、廃棄し、交換した。場合によっては、試験中に新たな追加の傷が発生したか否かを識別するために、ラミネートの傷に印を付けた。
30.8平方インチ(in2)(198.7平方センチメートル(cm2)で構成されるラミネートの各パウチに、試料当たり100 mLの3%酢酸を充填した。次に、パウチをレトルトチャンバーに移行し、121℃で2時間保管した。試験後、周囲温度まで冷却した後、酢酸をポリエチレンボトルに移行した。
一実施形態では、本発明は、溶剤系レトルト接着剤組成物であって、(A)少なくとも1つのイソシアネート化合物である成分Aと、(B)(i)少なくとも1つのリン酸エステル化合物、および(ii)3,000 g/mol以上の平均分子量を有する少なくとも1つのポリエステルポリオールを含む、少なくとも1つのイソシアネート反応性成分を含む、少なくとも1つのイソシアネート反応性成分である成分Bと、を含む、溶剤系レトルト接着剤組成物を含む。
Claims (10)
- 溶剤系レトルト接着剤組成物であって、
(A)少なくとも1つのイソシアネート化合物である成分Aと、
(B)(i)少なくとも1つのリン酸エステル化合物、および(ii)3,000 g/mol以上の平均分子量を有する少なくとも1つのポリエステルポリオールを含む、少なくとも1つのイソシアネート反応性成分である成分Bと、を含む、溶剤系レトルト接着剤組成物。 - 前記少なくとも1つのイソシアネート化合物である成分Aが、少なくとも1つの脂肪族系イソシアネートであるか、または前記少なくとも1つのイソシアネート化合物である成分Aが、(i)少なくとも1つの脂肪族系イソシアネートと(ii)少なくとも1つの芳香族系イソシアネートとのブレンドである、請求項1に記載の接着剤。
- 前記少なくとも1つの芳香族系イソシアネートである、成分Aの成分(ii)が、(α)少なくとも1つのイソシアネート化合物と、(β)少なくとも1つのポリオール化合物との反応生成物を含む、イソシアネートプレポリマーである、請求項2に記載の接着剤。
- 前記少なくとも1つのポリエステルポリオールである、成分Bの成分(ii)が、脂肪族ポリエステルポリオール、芳香族ポリエステルポリオール、脂肪族および芳香族ポリエステルポリオールのコポリマー、ポリカーボネートポリオール、ポリカプロラクトンポリオール、ならびにそれらの混合物からなる群から選択される、請求項1に記載の接着剤。
- 前記少なくとも1つのイソシアネート反応性成分である成分Bが、(iii)1,500 g/mol未満の平均分子量を有する少なくとも1つのポリエーテルポリオールをさらに含む、請求項1に記載の接着剤。
- ラミネートを生成するための溶剤系ポリウレタンレトルト接着剤組成物を生成するためのプロセスであって、
(A)少なくとも1つのイソシアネート化合物である成分Aと、
(B)(i)少なくとも1つのリン酸エステル化合物、および(ii)3,000 g/mol以上の平均分子量を有するポリエステルポリオールを含む、少なくとも1つのポリオールを含む、少なくとも1つのイソシアネート反応性成分である成分Bと、を混和することを含む、プロセス。 - 多層ラミネート生成物であって、
(a)少なくとも1つの第1の層と、
(b)少なくとも1つの第2の層と、
(c)前記第1の層と前記第2の層との間に配置された請求項1に記載のレトルト接着剤と、を含み、前記接着剤を硬化させて、前記第1の層を前記第2の層に結合させる、多層ラミネート生成物。 - ラミネート生成物を生成するためのプロセスであって、
(I)前記第1の層および/または前記第2の層の表面の少なくとも一部分に、請求項1に記載のレトルト接着剤を塗布するステップと、
(II)前記接着剤が、前記第1の層と前記第2の層との間に配置されるように、前記第1の層と前記第2の層とを接触させるステップと、
(III)前記接着剤を硬化させて、前記硬化された接着剤を介して前記第2の層に結合された前記第1の層を含むラミネートを形成するステップと、を含む、プロセス。 - 請求項8に記載のラミネートを含む、レトルト包装用の容器。
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US201962862714P | 2019-06-18 | 2019-06-18 | |
US62/862,714 | 2019-06-18 | ||
PCT/US2020/033617 WO2020256878A1 (en) | 2019-06-18 | 2020-05-19 | Retort adhesive composition |
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US11220617B2 (en) * | 2016-07-11 | 2022-01-11 | Dow Global Technologies Llc | High-solids content solvent-based adhesive compositions and methods of making same |
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