JP2020200430A - ポリウレタンディスパージョンおよびその製造方法 - Google Patents
ポリウレタンディスパージョンおよびその製造方法 Download PDFInfo
- Publication number
- JP2020200430A JP2020200430A JP2019110364A JP2019110364A JP2020200430A JP 2020200430 A JP2020200430 A JP 2020200430A JP 2019110364 A JP2019110364 A JP 2019110364A JP 2019110364 A JP2019110364 A JP 2019110364A JP 2020200430 A JP2020200430 A JP 2020200430A
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- Prior art keywords
- mass
- ammonia
- polyurethane
- polyurethane dispersion
- 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
- 229920003009 polyurethane dispersion Polymers 0.000 title claims abstract description 119
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 198
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 88
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 80
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 71
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims abstract description 69
- -1 hydrogen compound Chemical class 0.000 claims abstract description 55
- 239000012948 isocyanate Substances 0.000 claims abstract description 52
- 150000002513 isocyanates Chemical group 0.000 claims abstract description 52
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 51
- 125000000129 anionic group Chemical group 0.000 claims abstract description 42
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 33
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 150000002009 diols Chemical class 0.000 claims abstract description 22
- 239000004970 Chain extender Substances 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 238000010517 secondary reaction Methods 0.000 claims abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 abstract description 65
- 239000004814 polyurethane Substances 0.000 abstract description 65
- 239000007789 gas Substances 0.000 abstract description 38
- 230000004888 barrier function Effects 0.000 abstract description 34
- 238000003860 storage Methods 0.000 abstract description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
- 229920005862 polyol Polymers 0.000 description 62
- 150000003077 polyols Chemical class 0.000 description 58
- 239000010410 layer Substances 0.000 description 56
- 239000007787 solid Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 36
- 238000000034 method Methods 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 32
- 239000000945 filler Substances 0.000 description 30
- 239000002585 base Substances 0.000 description 28
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 22
- 235000011114 ammonium hydroxide Nutrition 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 19
- 239000010408 film Substances 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 16
- 238000006467 substitution reaction Methods 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 229920000768 polyamine Polymers 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 239000002734 clay mineral Substances 0.000 description 10
- 229920005906 polyester polyol Polymers 0.000 description 10
- 125000005270 trialkylamine group Chemical group 0.000 description 10
- 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 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 150000002484 inorganic compounds Chemical class 0.000 description 9
- 229910010272 inorganic material Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000010445 mica Substances 0.000 description 8
- 229910052618 mica group Inorganic materials 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 208000008469 Peptic Ulcer Diseases 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 6
- 229920005992 thermoplastic resin Polymers 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 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
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 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 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002121 nanofiber Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 3
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 239000002253 acid Substances 0.000 description 3
- 230000004520 agglutination Effects 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000013078 crystal Substances 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 238000001879 gelation Methods 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
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 238000010572 single replacement reaction Methods 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-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
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-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
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 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
- 125000003277 amino group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 239000007853 buffer solution Substances 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
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- 239000003086 colorant Substances 0.000 description 2
- 238000013329 compounding Methods 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
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 2
- 229910052622 kaolinite Inorganic materials 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
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- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
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- 238000004445 quantitative analysis Methods 0.000 description 2
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- 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 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- GHXPTDPKJYFMOE-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCCC1CN=C=O GHXPTDPKJYFMOE-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
ポリウレタンディスパージョン中の中和剤において、アンモニアおよびトリエチルアミンの含有割合を、電気泳動システムにより定量した。
(装置および測定条件)
装置:Agilent Technologies社製 7100キャピラリー電気泳動システム
緩衝液:Agilent Technologies社製 有害陰イオン分析緩衝液
そして、1点検量線法によって、アンモニアの含有量、および、トリエチルアミンの含有量を求め、それらの質量比率を算出した。
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)170.7g、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)29.8g、エチレングリコール34.4g、トリメチロールプロパン2.6g、ジメチロールプロピオン酸19.6gおよび溶剤としてメチルエチルケトン146.2gを混合し、窒素雰囲気下65〜70℃で、イソシアネート基濃度(溶剤を除いた固形分あたりのNCO%)が9.53%に至るまで反応させ、イソシアネート基末端プレポリマーを含む反応液を得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
表1に示す処方に従って、比較例1と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
置換用中和剤として、25質量%濃度のアンモニア水に代えて、トリイソプロパノールアミン27.3gを水109.3gで希釈した水溶液を使用した以外は、比較例2(1回置換)と同じ方法で、ポリウレタンディスパージョン9(二次ポリウレタンディスパージョン、PUD9)を得た。
置換用中和剤として、25質量%濃度のアンモニア水に代えて、トリエタノールアミン21.3gを水85.2gで希釈した水溶液を使用した以外は、比較例2(1回置換)と同じ方法で、ポリウレタンディスパージョン10(二次ポリウレタンディスパージョン、PUD10)を得た。
表2に記載の配合で、比較例1と同様にして、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)と、エチレングリコールと、ジメチロールプロピオン酸とを、アセトニトリル存在下、窒素雰囲気化65〜70℃で、イソシアネート基濃度(溶剤を除いた固形分あたりのNCO%)が15.73%に至るまで反応させ、イソシアネート基末端プレポリマーを含む反応液を得た。
表2に示す処方に従って、比較例5と同じ方法で、脱溶剤前の一次ポリウレタンディスパージョンを得た。
置換用中和剤として、25質量%濃度のアンモニア水に代えて、水酸化ナトリウム4.9gを水157.0gで希釈した水溶液を使用した以外は、比較例2(1回置換)と同じ方法で、ポリウレタンディスパージョン13(二次ポリウレタンディスパージョン、PUD13)を得た。
置換用中和剤として、25質量%濃度のアンモニア水に代えて、水酸化リチウム2.9gを水94.0gで希釈した水溶液を使用した以外は、比較例2(1回置換)と同じ方法で、ポリウレタンディスパージョン14(二次ポリウレタンディスパージョン、PUD14)を得た。
<ポリウレタンディスパージョンの評価>
(1)保存安定性(熱安定性)
濃厚系粒子径アナライザーFPAR−1000(大塚電子株式会社製)を用いて、PUDの粒子径D1を測定した。
PUD 100gを、マロン型試験機(マロン式機械的安定度試験機 AB−802、テスター産業製)にて、荷重15kg、回転数1,000rpmで15分間処理した。
(ポリウレタン樹脂の凝集率(%))=[(凝集物濃度)/(固形分濃度)]×100
なお、数値が小さいほど、機械的安定性が高いことを示す。
(3)ガスバリア性
基材としてのポリエチレンテレフタレートフィルム(二軸延伸ポリエステルフィルム、商品名:東洋紡エステルフィルムE5102、東洋紡社製、厚み12μm)に、乾燥時の厚みが3g/m2となるように、バーコーターを用いてPUDを塗布した。
基材としてのポリエチレンテレフタレートフィルム(二軸延伸ポリエステルフィルム、商品名:東洋紡エステルフィルムE5102、東洋紡社製、厚み12μm)に、乾燥時の厚みが3g/m2となるように、バーコーターを用いてPUDを塗布した。
2 基材
3 ポリウレタン層
Claims (3)
- 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有するポリイソシアネート成分と、炭素数2〜6の短鎖ジオール、および、アニオン性基を含有する活性水素化合物を含有する活性水素基含有成分との一次反応生成物であるイソシアネート基末端プレポリマーと、鎖伸長剤との二次反応生成物であり、
前記アニオン性基が、アンモニアを含有する中和剤により中和されており、
前記中和剤の総量に対して、アンモニアの含有割合が、30モル%以上である
ことを特徴とする、ポリウレタンディスパージョン。 - 前記中和剤が、アンモニアおよび3級アミンからなり、
前記中和剤の総量に対して、アンモニアの含有割合が、30モル%以上95モル%以下であり、前記3級アミンの含有割合が、5モル%以上70モル%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。 - 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を製造するためのポリウレタンディスパージョンの製造方法であり、
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有するポリイソシアネート成分と、炭素数2〜6の短鎖ジオール、および、アニオン性基を含有する活性水素化合物を含有する活性水素基含有成分とを反応させてイソシアネート基末端プレポリマーを得る工程と、
前記イソシアネート基末端プレポリマーのアニオン性基を、3級アミンからなる一次中和剤により中和する工程と、
一次中和剤により中和された前記イソシアネート基末端プレポリマーと、鎖伸長剤とを反応させてポリウレタン樹脂を得る工程と、
前記ポリウレタン樹脂において、前記一次中和剤の少なくとも一部をアンモニアで置換し、アンモニアを含有する二次中和剤によってアニオン性基を中和させる工程と
を備える
ことを特徴とする、ポリウレタンディスパージョンの製造方法。
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WO2007148801A1 (ja) * | 2006-06-23 | 2007-12-27 | Nippon Steel Corporation | 表面処理金属材及び金属表面処理剤 |
JP2010043168A (ja) * | 2008-08-11 | 2010-02-25 | Nippon Steel Corp | 表面処理金属材及び金属表面処理剤 |
WO2019004349A1 (ja) * | 2017-06-29 | 2019-01-03 | Dic株式会社 | ウレタン樹脂組成物、鋼板表面処理剤及びその塗膜を有する鋼板 |
WO2019230393A1 (ja) * | 2018-06-01 | 2019-12-05 | 第一工業製薬株式会社 | フィルムコーティング剤 |
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JP2008025023A (ja) * | 2006-06-23 | 2008-02-07 | Nippon Steel Corp | 表面処理金属材及び金属表面処理剤 |
JP2010043168A (ja) * | 2008-08-11 | 2010-02-25 | Nippon Steel Corp | 表面処理金属材及び金属表面処理剤 |
WO2019004349A1 (ja) * | 2017-06-29 | 2019-01-03 | Dic株式会社 | ウレタン樹脂組成物、鋼板表面処理剤及びその塗膜を有する鋼板 |
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