JP6306448B2 - ポリウレタンディスパージョンおよびポリウレタン積層体 - Google Patents
ポリウレタンディスパージョンおよびポリウレタン積層体 Download PDFInfo
- Publication number
- JP6306448B2 JP6306448B2 JP2014130025A JP2014130025A JP6306448B2 JP 6306448 B2 JP6306448 B2 JP 6306448B2 JP 2014130025 A JP2014130025 A JP 2014130025A JP 2014130025 A JP2014130025 A JP 2014130025A JP 6306448 B2 JP6306448 B2 JP 6306448B2
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- Japan
- Prior art keywords
- group
- polyurethane
- mass
- less
- xylylene diisocyanate
- 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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- 229920002635 polyurethane Polymers 0.000 title claims description 92
- 239000004814 polyurethane Substances 0.000 title claims description 92
- 229920003009 polyurethane dispersion Polymers 0.000 title claims description 79
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 229910001868 water Inorganic materials 0.000 claims description 78
- 229920005862 polyol Polymers 0.000 claims description 70
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 69
- 150000003077 polyols Chemical class 0.000 claims description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 239000012948 isocyanate Substances 0.000 claims description 46
- 150000002513 isocyanates Chemical group 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 239000005056 polyisocyanate Substances 0.000 claims description 40
- 229920001228 polyisocyanate Polymers 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229920005749 polyurethane resin Polymers 0.000 claims description 39
- 150000002484 inorganic compounds Chemical class 0.000 claims description 36
- 229910010272 inorganic material Inorganic materials 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 22
- 238000001035 drying Methods 0.000 claims description 21
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 19
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000004970 Chain extender Substances 0.000 claims description 12
- -1 alkyl glycol Chemical compound 0.000 description 82
- 239000010410 layer Substances 0.000 description 70
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 67
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 64
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
- 230000004888 barrier function Effects 0.000 description 41
- 239000011248 coating agent Substances 0.000 description 39
- 239000007789 gas Substances 0.000 description 35
- 239000000126 substance Substances 0.000 description 35
- 239000010408 film Substances 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 27
- 239000003999 initiator Substances 0.000 description 26
- 238000005342 ion exchange Methods 0.000 description 26
- 239000002585 base Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- 239000012295 chemical reaction liquid Substances 0.000 description 20
- 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 19
- 239000002253 acid Substances 0.000 description 16
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 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 14
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000005058 Isophorone diisocyanate Substances 0.000 description 13
- 125000003277 amino group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 11
- 229920000768 polyamine Polymers 0.000 description 11
- 230000001954 sterilising effect Effects 0.000 description 11
- 238000004659 sterilization and disinfection Methods 0.000 description 11
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000002734 clay mineral Substances 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- 230000032683 aging Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229920002799 BoPET Polymers 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 8
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 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 7
- 125000002723 alicyclic group Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 125000003010 ionic group Chemical group 0.000 description 7
- 229940059574 pentaerithrityl Drugs 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 6
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 6
- 229910052618 mica group Inorganic materials 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 229920000193 polymethacrylate Polymers 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000005001 laminate film Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000011435 rock Substances 0.000 description 5
- 229920005992 thermoplastic resin Polymers 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 238000012662 bulk polymerization Methods 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000007809 chemical reaction catalyst Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000010445 mica Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000005033 polyvinylidene chloride Substances 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- RJDOZRNNYVAULJ-UHFFFAOYSA-L [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] RJDOZRNNYVAULJ-UHFFFAOYSA-L 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000000071 blow moulding Methods 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
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- 238000010894 electron beam technology Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
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- CWBIFDGMOSWLRQ-UHFFFAOYSA-N trimagnesium;hydroxy(trioxido)silane;hydrate Chemical compound O.[Mg+2].[Mg+2].[Mg+2].O[Si]([O-])([O-])[O-].O[Si]([O-])([O-])[O-] CWBIFDGMOSWLRQ-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
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Images
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- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
アシルホスフィンオキシド系光重合開始剤としては、例えば、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキシド(例えば、BASF社製、ルシリンTPO)、ビス(2,6−ジメトキシベンゾイル)−2,4,4−トリメチルペンチルホスフィンオキシド(BAPO)、ビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキシド、ビス(2,4,6−トリメチルベンゾイル)エチルホスフィンオキシド、ビス(2,4,6−トリメチルベンゾイル)n−ブチルホスフィンオキシドなどが挙げられる。
これら光重合開始剤は、単独使用または2種以上併用することができる。好ましくは、アセトフェノン系光重合開始剤が挙げられる。
<ポリウレタンディスパージョン(PUD)の調製>
実施例1(PUD1)
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)78.4g、タケネート600(1,3−ビス(イソシアナトメチル)シクロヘキサン、1,3−H6XDI、三井化学社製)80.9g、エチレングリコール22.9g、トリメチロールプロパン5.3g、ジメチロールプロピオン酸14.4gおよび溶剤としてメチルエチルケトン121.9gを混合し、窒素雰囲気下65〜70℃で4時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)89.6g、タケネート600(1,3−ビス(イソシアナトメチル)シクロヘキサン、1,3−H6XDI、三井化学社製)61.6g、エチレングリコール15.8g、トリメチロールプロパン7.6g、ジメチロールプロピオン酸15.2gおよび溶剤としてメチルエチルケトン122.5gを混合し、窒素雰囲気下65〜70℃で3時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)107.5g、タケネート600(1,3−ビス(イソシアナトメチル)シクロヘキサン、1,3−H6XDI、三井化学社製)55.5g、エチレングリコール26.2g、トリメチロールプロパン4.9g、ジメチロールプロピオン酸14.8gおよび溶剤としてメチルエチルケトン121.6gを混合し、窒素雰囲気下65〜70℃で4時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)143.7g、エチレングリコール16.9g、トリメチロールプロパン4.9g、DIOL400(ポリオキシプロピレンエーテルグリコール、数平均分子量400、三井化学社製)28.4g、ジメチロールプロピオン酸14.6gおよび溶剤としてメチルエチルケトン123.0gを混合し、窒素雰囲気下65〜70℃で4時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)136.9g、VestanatH12MDI(4,4’−メチレンビス(シクロヘキシルイソシアネート)、H12MDI、エボニック社製)23.9g、エチレングリコール22.5g、トリメチロールプロパン5.2g、ジメチロールプロピオン酸14.1gおよび溶剤としてメチルエチルケトン122.2gを混合し、窒素雰囲気下65〜70℃で4時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)157.2g、エチレングリコール21.4g、トリメチロールプロパン5.2g、ジメチロールプロピオン酸15.1gおよび溶剤としてメチルエチルケトン120.8gを混合し、窒素雰囲気下65〜70℃で3時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート600(1,3−ビス(イソシアナトメチル)シクロヘキサン、1,3−H6XDI、三井化学社製)160.6g、エチレングリコール24.3g、トリメチロールプロパン5.6g、ジメチロールプロピオン酸14.6gおよび溶剤としてメチルエチルケトン123.7gを混合し、窒素雰囲気下70〜75℃で3時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート500(1,3−キシリレンジイソシアネート、m−XDI、三井化学社製)82.09g、タケネート600(1,3−ビス(イソシアナトメチル)シクロヘキサン、1,3−H6XDI、三井化学社製)84.6g、エチレングリコール29.7g、トリメチロールプロパン2.8g、ジメチロールプロピオン酸15.0gおよび溶剤としてメチルエチルケトン121.3gを混合し、窒素雰囲気下65〜70℃でNCO%が6.24%以下になるまで反応させ、ビニル基を含有しない透明なイソシアネート基含有プレポリマー反応液を得た。
VestanatIPDI(イソホロンジイソシアネート、IPDI、エボニック社製)93.3g、ネオペンチルグリコール12.5g、タケラックU−7020(ポリエステルポリオール、数平均分子量2000、三井化学社製)150.0g、ジメチロールプロピオン酸14.1gおよび溶剤としてアセトン151.1gを混合し、窒素雰囲気下50〜55℃で、ウレタン化反応触媒としてオクチル酸第一錫0.03gにてNCO%が2.40%以下になるまで反応させ、ビニル基を含有しない透明なイソシアネート基含有プレポリマー反応液を得た。
VestanatIPDI(イソホロンジイソシアネート、IPDI、エボニック社製)111.8g、ネオペンチルグリコール7.5g、トリメチロールプロパン3.2g、タケラックU−7020(ポリエステルポリオール、数平均分子量2000、三井化学社製)107.9g、ジメチロールプロピオン酸16.9gおよび溶剤としてアセトン149.0gを混合し、窒素雰囲気下50〜55℃で、ウレタン化反応触媒としてオクチル酸第一錫0.03gとともに5時間反応させ、イソシアネート基末端プレポリマーを得た。
タケネート700(ヘキサメチレンジイソシアネート、HDI、三井化学社製)26.0g、VestanatIPDI(イソホロンジイソシアネート、IPDI、エボニック社製)137.4g、エチレングリコール19.8g、トリメチロールプロパン4.3g、ジメチロールプロピオン酸14.3gおよび溶剤としてメチルエチルケトン121.8gを混合し、窒素雰囲気下75〜80℃で3時間反応させ、イソシアネート基末端プレポリマーを得た。
XDI:タケネート500、1,3−キシリレンジイソシアネート、m−XDI、三井化学社製
H6XDI:タケネート600、1,3−ビス(イソシアナトメチル)シクロヘキサン、1,3−H6XDI、三井化学社製
H12MDI:VestanatH12MDI、4,4’−メチレンビス(シクロヘキシルイソシアネート、エボニック社製
HDI:タケネート700、ヘキサメチレンジイシソアネート、HDI、三井化学社製
IPDI:VestanatIPDI、イソホロンジイソシアネート、IPDI、エボニック社製
EG:エチレングリコール
NPG:ネオペンチルグリコール
TMP:トリメチロールプロパン
PP440:DIOL400、ポリオキシプロピレンエーテルグリコール、数平均分子量400、三井化学社製
U−7020:タケラックU−7020、ポリエステルポリオール、数平均分子量2000、三井化学社製
DMPA:ジメチロールプロピオン酸
2HEA:2−ヒドロキシエチルアクリレート
MEK:メチルエチルケトン
TEA:トリエチルアミン
AEA:2−((2−アミノエチル)アミノ)エタノール
IPDA:イソホロンジアミン
<ポリウレタン積層体の作成>
実施例8(積層体1)
20gのPUD1をマグネチックスターラーにて攪拌し、これに25gのイオン交換水および5gの2−プロパノールを徐々に添加した。次いで0.15gのDAROCUR1173(2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、光重合開始剤、チバ・スペシャルティ・ケミカルズ社製)を添加、30分混合してコート剤1を調製した。
表2に示す配合処方とした以外は、実施例8(積層体1)と同様に、コート剤2〜5および7〜8を調製し、積層体2〜5および7〜8を得た。
20gのPUD1をマグネチックスターラーにて攪拌し、これに25gのイオン交換水を添加した。次に、2−プロパノール5gにペンタエリスリトールトリアクリレート(光重合性化合物、A−TMM−3LM−N;新中村化学社製)0.5gを溶解したアクリレート/アルコール溶液を徐々に添加して混合した後、0.15gのDAROCUR1173(2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、光重合開始剤、チバ・スペシャルティ・ケミカルズ社製)を添加し、30分混合してコート剤6を調製した。
20gのPUD−H1をマグネチックスターラーにて攪拌し、これに25gのイオン交換水および5gの2−プロパノールを徐々に添加、混合してコート剤9を調製した。
16.67gのPUD−H2をマグネチックスターラーにて攪拌し、これに28.33gのイオン交換水および5gの2−プロパノールを徐々に添加、混合してコート剤10を調製した。
16.67gのPUD−H3をマグネチックスターラーにて攪拌し、これに28.33gのイオン交換水および5gの2−プロパノールを徐々に添加した。次いで0.15gのDAROCUR1173(2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、光重合開始剤、チバ・スペシャルティ・ケミカルズ社製)を添加し、30分混合してコート剤11を調製した。
16gのPUD−H1をマグネチックスターラーにて攪拌し、これに28gのイオン交換水、および5gの2−プロパノールを徐々に添加した。次いで、1gのタケネートWD−725(硬化剤、水分散性ポリイソシアネート、三井化学社製)を添加し、30分混合してコート剤12を調製した。
16gのPUD−H1をマグネチックスターラーにて攪拌し、これに26.5gのイオン交換水、および5gの2−プロパノールを徐々に添加した。次いで、1gのカルボジライトV−02(架橋剤、ポリカルボジイミド化合物、日清紡ケミカル社製)を添加、30分混合してコート剤13を調製した。
20gのPUD−H4をマグネチックスターラーにて攪拌し、これに25gのイオン交換水および5gの2−プロパノールを徐々に添加した。次いで0.15gのDAROCUR1173(2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、光重合開始剤、チバ・スペシャルティ・ケミカルズ社製)を添加、30分混合してコート剤14を調製した。
<ラミネートフィルムの作成>
積層体1〜14のコート面に、ドライラミネート用接着剤としてタケラックA−310(三井化学社製)とタケネートA−3(三井化学社製)との混合物(タケラックA−310/タケネートA−3=10/1(質量比))を乾燥厚み3g/m2となるようにバーコーターにて塗布し、ドライヤーで乾燥させた。
<熱水殺菌処理>
ラミネートフィルムの作成で得られたラミネートフィルム1〜14を、120℃×30分間、0.2MPaの加圧下で、熱水滅菌処理した。
<酸素透過度の測定>
酸素透過測定装置(OX−TRAN2/20、MOCON社製)を用いて、各ラミネートフィルムそれぞれの20℃における、相対湿度80%(80%RH)での1m2、1日および1気圧当たりの酸素透過量を、熱水殺菌処理前後で測定した。
<密着性(ラミネート強度)の測定>
各ラミネートフィルムの基材とポリウレタン層との間のラミネート強度を、JIS K 6854に準拠したT字剥離試験(15mm幅)を熱水殺菌処理前後で測定した。その結果を表2に示す。
DAROCUR1173:2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、光重合開始剤、チバ・スペシャルティ・ケミカルズ社製
タケネートWD−725:水分散ポリイソシアネート(硬化剤)、三井化学社製
カルボジライトV−02:ポリカルボジイミド化合物(架橋剤)、日清紡ケミカル社製
1011HG:バリアロックス1011HG(#12)、東レフィルム加工社製
2 基材
3 ポリウレタン層
Claims (7)
- ポリウレタン樹脂が、水分散されてなるポリウレタンディスパージョンであって、
前記ポリウレタン樹脂は、
キシリレンジイソシアネートおよび/または水添キシリレンジイソシアネートを含むポリイソシアネート成分と、
炭素数2〜6のジオール、水酸基を含有するビニルモノマー、および、親水性基を含有する活性水素基含有化合物を含み、数平均分子量400以上の高分子量ポリオールを含まない活性水素基含有成分と
を少なくとも反応させることにより得られることを特徴とする、ポリウレタンディスパージョン。 - 前記ポリウレタン樹脂のビニル基当量が、500g/eq.以上10000g/eq.以下であることを特徴とする、請求項1に記載のポリウレタンディスパージョン。
- 前記ポリウレタン樹脂のウレタン基濃度およびウレア基濃度の合計が、25質量%以上50質量%以下であることを特徴とする、請求項1または2に記載のポリウレタンディスパージョン。
- 前記キシリレンジイソシアネートおよび前記水添キシリレンジイソシアネートの総量の含有割合が、前記ポリイソシアネート成分の総量に対して、50質量%以上であることを特徴とする、請求項1〜3のいずれか一項に記載のポリウレタンディスパージョン。
- 前記ポリウレタン樹脂が、
まず、キシリレンジイソシアネートおよび/または水添キシリレンジイソシアネートを含むポリイソシアネート成分と、炭素数2〜6のジオール、および、親水性基を含有する活性水素基含有化合物を含み、数平均分子量400以上の高分子量ポリオールを含まない活性水素基含有成分とを少なくとも反応させ、イソシアネート基末端プレポリマーを合成し、
次いで、得られた前記イソシアネート基末端プレポリマーと、水酸基を含有するビニルモノマーを含み、数平均分子量400以上の高分子量ポリオールを含まない活性水素基含有成分とを少なくとも反応させ、ビニル基含有イソシアネート基末端プレポリマーを合成し、
その後、得られた前記ビニル基含有イソシアネート基末端プレポリマーと、鎖伸長剤を含み、数平均分子量400以上の高分子量ポリオールを含まない活性水素基含有成分とを少なくとも反応させる
ことにより得られることを特徴とする、請求項1〜4のいずれか一項に記載のポリウレタンディスパージョン。 - 基材と、
前記基材の上に積層され、ポリウレタン樹脂からなるポリウレタン層とを備え、
前記ポリウレタン層が、
請求項1〜5のいずれか一項に記載のポリウレタンディスパージョンを塗布および乾燥させることにより形成されていることを特徴とする、ポリウレタン積層体。 - 前記ポリウレタン層に、層状無機化合物が分散されていることを特徴とする、請求項6に記載のポリウレタン積層体。
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JP5016266B2 (ja) * | 2006-06-30 | 2012-09-05 | 三井化学株式会社 | 光学プラスチックレンズ用プライマー |
JP5375255B2 (ja) * | 2009-03-27 | 2013-12-25 | 東レ株式会社 | 蒸着用フィルムおよびガスバリアフィルム |
JP2013208901A (ja) * | 2012-02-28 | 2013-10-10 | Toppan Printing Co Ltd | ガスバリア性積層体 |
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