CN112739786B - Composition for aqueous coating solutions comprising polymers of N-vinylcarboxylic acid amides - Google Patents
Composition for aqueous coating solutions comprising polymers of N-vinylcarboxylic acid amides Download PDFInfo
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- CN112739786B CN112739786B CN201980061889.5A CN201980061889A CN112739786B CN 112739786 B CN112739786 B CN 112739786B CN 201980061889 A CN201980061889 A CN 201980061889A CN 112739786 B CN112739786 B CN 112739786B
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- China
- Prior art keywords
- composition
- polymer
- acid amide
- vinylcarboxylic acid
- aqueous coating
- Prior art date
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- 238000000576 coating method Methods 0.000 title claims abstract description 72
- 239000011248 coating agent Substances 0.000 title claims abstract description 70
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 229920000642 polymer Polymers 0.000 title claims abstract description 66
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical class C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000001035 drying Methods 0.000 claims abstract description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 150000004676 glycans Chemical class 0.000 claims abstract description 31
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 31
- 239000005017 polysaccharide Substances 0.000 claims abstract description 31
- 239000007788 liquid Substances 0.000 claims abstract description 25
- -1 alkali metal salt Chemical class 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 20
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical group CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 7
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 7
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 25
- 238000000034 method Methods 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 18
- 229920003169 water-soluble polymer Polymers 0.000 description 16
- 239000003505 polymerization initiator Substances 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 235000010980 cellulose Nutrition 0.000 description 6
- 229920000126 latex Polymers 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007870 radical polymerization initiator Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 230000008719 thickening Effects 0.000 description 5
- BSXGCUHREZFSRY-UHFFFAOYSA-N 3-[[1-amino-2-[[1-amino-1-(2-carboxyethylimino)-2-methylpropan-2-yl]diazenyl]-2-methylpropylidene]amino]propanoic acid;tetrahydrate Chemical compound O.O.O.O.OC(=O)CCNC(=N)C(C)(C)N=NC(C)(C)C(=N)NCCC(O)=O BSXGCUHREZFSRY-UHFFFAOYSA-N 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000004566 building material Substances 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229910001416 lithium ion Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000007717 redox polymerization reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 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
- 239000011230 binding agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LHDAOBIMYRBCKE-UHFFFAOYSA-N N-(ethoxymethyl)-N-(propoxymethyl)prop-2-enamide Chemical compound CCCOCN(C(=O)C=C)COCC LHDAOBIMYRBCKE-UHFFFAOYSA-N 0.000 description 2
- 229920001145 Poly(N-vinylacetamide) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- LSWADWIFYOAQRZ-UHFFFAOYSA-N n-(ethoxymethyl)prop-2-enamide Chemical compound CCOCNC(=O)C=C LSWADWIFYOAQRZ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000007774 positive electrode material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- ZYEGQWAZDWQNHB-UHFFFAOYSA-M sodium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane;hydron Chemical compound [H+].[Na+].[O-]S([S-])(=O)=O ZYEGQWAZDWQNHB-UHFFFAOYSA-M 0.000 description 2
- 239000011115 styrene butadiene Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- PITLEXLWAKFCAI-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCOCC(O)OC1=CC=CC=C1 PITLEXLWAKFCAI-UHFFFAOYSA-N 0.000 description 1
- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- VLTSFMBMFCXCKB-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-phenoxyethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCOCCOCCOCC(O)OC1=CC=CC=C1 VLTSFMBMFCXCKB-UHFFFAOYSA-N 0.000 description 1
- TVFJLSWPPLFHKR-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCCOCCOCC(O)OC1=CC=CC=C1 TVFJLSWPPLFHKR-UHFFFAOYSA-N 0.000 description 1
- XMIYEVCXHOOJMF-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]-1-phenoxyethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCOCCOCCOCCOCCOCC(O)OC1=CC=CC=C1 XMIYEVCXHOOJMF-UHFFFAOYSA-N 0.000 description 1
- ADRHDZXSVIPHAF-UHFFFAOYSA-N 2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCCOCCOCCOCCOCC(O)OC1=CC=CC=C1 ADRHDZXSVIPHAF-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
- LRRBANSQUYNJTH-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylpropane;2-ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O.CC(C)(C)OOC(C)(C)C LRRBANSQUYNJTH-UHFFFAOYSA-N 0.000 description 1
- MNULHGQAROOBFB-UHFFFAOYSA-N 3-[(1-amino-2-methylpropylidene)amino]propanoic acid Chemical compound CC(C)C(N)=NCCC(O)=O MNULHGQAROOBFB-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- ZRVIYEJYXIDATJ-UHFFFAOYSA-N 4-Heptyloxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1 ZRVIYEJYXIDATJ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910014195 BM-400B Inorganic materials 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102100034983 E3 ubiquitin-protein ligase ZNRF4 Human genes 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229920002148 Gellan gum Polymers 0.000 description 1
- 229920000569 Gum karaya Polymers 0.000 description 1
- 101000802410 Homo sapiens E3 ubiquitin-protein ligase ZNRF4 Proteins 0.000 description 1
- 101000614988 Homo sapiens Mediator of RNA polymerase II transcription subunit 12 Proteins 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 102100021070 Mediator of RNA polymerase II transcription subunit 12 Human genes 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
- C09D101/08—Cellulose derivatives
- C09D101/10—Esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D103/00—Coating compositions based on starch, amylose or amylopectin or on their derivatives or degradation products
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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Abstract
A constitution is proposed which enables efficient drying when a coating is produced from an aqueous composition containing a polymer of an N-vinylcarboxylic acid amide. A composition for an aqueous coating liquid, comprising at least a polymer of an N-vinylcarboxylic acid amide, a polysaccharide and water.
Description
Technical Field
The present invention relates to a composition containing a polymer of an N-vinylcarboxylic acid amide as a water-soluble polymer, and mainly relates to a composition capable of forming an easily dryable coating on a construction surface in an aqueous coating solution containing a water-soluble polymer such as a paint, an ink, an adhesive, a positive electrode, a negative electrode, and a separator of a lithium ion battery.
Background
In all industrial fields, coating and printing techniques using water-soluble polymers have been widely used from the viewpoints of environmental aspects, safety aspects, and efficiency. In particular, when a film is formed, an aqueous coating liquid using a water-soluble polymer is excellent, and has a great industrial advantage.
Among them, poly-N-vinylacetamide (hereinafter, also referred to as PNVA (registered trademark)) which is 1 kind of polymer of N-vinylcarboxylic acid amide is also used for various applications such as thickening, film formation, and adhesives of aqueous inks, paints, and various aqueous coating liquids because it is amphiphilic and is easily increased in molecular weight and viscosity. In particular, the resin is used as an adhesive, a coating material, a building material, or a binder resin for secondary batteries in the personal care field such as medicines and cosmetics, the construction field such as building materials, and the industrial field.
However, when a water-soluble polymer such as a polymer of N-vinylcarboxylic acid amide or the like is dissolved in water as a solvent and used, if a part of a high-boiling organic solvent is removed, drying efficiency is often significantly inferior to that in the case of using an organic solvent.
In addition, although non-hydrophilic polymer emulsions and rubber latexes are sometimes used as aqueous coating liquids in applications where film properties are not expected, if these are compared with water-soluble polymers, the drying rates are greatly different, and there is a problem that it takes time to dry the water-soluble polymers. There are many problems in that a polymer emulsion or a rubber latex cannot be expected to be thickened as a binder for coating and the coated surface is brittle.
In general, improvement of the drying efficiency is often dealt with by improvement of the equipment and optimization of the drying conditions.
The improvement of the apparatus is naturally limited because it is often expensive and the influence of the increase in the temperature and the volume of hot air on the object to be dried is not small.
Furthermore, if consideration is given to energy saving, it is necessary to avoid unnecessary increase in energy consumption due to increase in drying temperature, increase in air volume, and the like.
In particular, in the production of secondary batteries such as lithium ion batteries, the coating material is required to be thin in view of weight reduction, high density, and the like. Therefore, the direction of increasing energy consumption in the production process is very unfavorable in consideration of environmental protection, and therefore, it is recognized as a necessary technique to increase the drying rate of a coating material containing a water-soluble polymer.
As a conventional technique related to improvement of the drying method of an aqueous coating liquid, there are the following techniques.
For example, patent document 1 discloses a drying method in which a coating liquid is irradiated with near infrared rays from a short distance of 10 to 35cm and air is blown to cure a coating material, but this method is an improvement in drying conditions and is not an improvement in drying properties of an adhesive itself.
As a method for improving the drying property of the aqueous medium substance, it is conceivable to add inorganic fillers, non-hydrophilic resins, and the like to the emulsion, but the method is not necessarily applicable to a coating liquid containing a water-soluble polymer.
For example, patent document 2 describes a composition in which talc is added to an aqueous dispersion emulsion as a base conditioner for a cement-based base material, but the application range is limited as a method for improving the drying property of a coating liquid containing a water-soluble polymer for the purpose of natural drying or drying by air drying.
Further, patent document 3 discloses an adhesive composition containing thermoplastic resin powder such as acrylic resin in an aqueous resin dispersion containing a styrene-butadiene copolymer latex and a chloroprene rubber latex. However, when a water-soluble polymer is used, it is often difficult to add a water-insoluble substance itself, and the range of application is extremely narrow because the amount to be added is limited.
Patent document 4 discloses a thickening/dispersing agent for a slurry for a positive electrode of a lithium ion secondary battery, which contains 1 or more kinds of water-soluble polymers such as carboxymethyl cellulose and poly N-vinylacetamide. However, it improves the adhesion between the positive electrode active materials and the positive electrode active material and the current collector, and the thickening dispersant concentration in the slurry for positive electrode is low, and further, the problem of drying is not disclosed or suggested.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 6-170327
Patent document 2: japanese patent No. 5433149
Patent document 3: japanese patent laid-open No. 2009-102606
Patent document 4: WO2015/146649 publication
Disclosure of Invention
Problems to be solved by the invention
In general, when the drying property of a coating liquid containing a water-soluble polymer is improved, the addition of a non-hydrophilic resin or the like to the original composition is not always possible, and when the addition is possible, there are many cases where the limitation is imposed on the amount, and the effectiveness is not often exerted.
In fact, there is no proposal of a constitution which enables efficient drying when a coating is formed from an aqueous composition in which a polymer of an N-vinylcarboxylic acid amide is dissolved.
Means for solving the problems
Under such circumstances, the present inventors have conducted intensive studies and as a result, have found that drying properties are significantly improved by mixing a polysaccharide with an N-vinylcarboxylic acid amide polymer which is a water-soluble polymer, and have completed the present invention.
That is, the present invention is configured as follows.
[1] A composition for an aqueous coating liquid, comprising at least a polymer of an N-vinylcarboxylic acid amide, a polysaccharide and water.
[2] The composition for aqueous coating solutions according to [1], wherein the N-vinylcarboxylic acid amide is N-vinylacetamide.
[3] The composition for an aqueous coating solution according to [1], wherein the polysaccharide is a cellulose derivative.
[4] The composition for an aqueous coating solution according to [3], wherein the cellulose derivative is an alkali (earth) metal salt of carboxymethyl cellulose.
[5] The composition for aqueous coating liquids according to [1] to [4], wherein the composition ratio of the polymer of the N-vinylcarboxylic acid amide to the polysaccharide is 95: 5-50: 50.
[6] the composition for aqueous coating liquids according to [1] to [5], further comprising an inorganic filler.
[7] The composition for an aqueous coating solution according to [6], wherein the inorganic filler is alumina.
[8] The composition for aqueous coating liquids according to [1] to [7], wherein the content of the N-vinylcarboxylic acid amide polymer in the composition is in the range of 0.05 to 20 mass%.
[9] A method for producing an aqueous polymer coating material, comprising applying the composition for an aqueous coating liquid according to any one of [1] to [8] to the surface of a substrate and drying the composition.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, since the polysaccharide is contained in the composition containing water and the polymer of N-vinylcarboxylic acid amide, the drying property is significantly improved when the composition is coated.
The composition of the present invention has a structure derived from an N-vinylcarboxylic acid amide, has high hydrophilicity because of retaining polarity, and has wetting, dispersing, thickening effects on various aqueous solutions and the like, and also has adhesiveness to various materials. Among them, the film has extremely high affinity for metal, glass, polypropylene, polyethylene terephthalate film, etc., and also has high adhesion to these materials.
Such a composition is suitably used in the fields where wetting, dispersing and thickening effects, adhesion effects and the like are required. In particular, the coating composition can be used as an adhesive, a coating material, a building material, or a coating solution for a secondary battery in the personal care field such as medicines and cosmetics, the construction field such as a building material, and the industrial field.
Detailed Description
The present invention will be described in detail below. The structure of the present invention is not limited to this.
Composition for aqueous coating liquid
The composition for an aqueous coating solution of the present invention contains at least water, a polymer of an N-vinylcarboxylic acid amide, and a polysaccharide as essential components. Examples of the coating liquid include adhesives, paints, inks, and positive electrodes, negative electrodes, separators, and the like of lithium ion batteries. Hereinafter, each component will be described.
Polymers of N-vinylcarboxylic acid amides
In the present invention, a polymer of N-vinylcarboxylic acid amide is used as the water-soluble polymer.
The N-vinylcarboxylic acid amide is represented by the following formula (1).
(in the general formula (1), R1Is any 1 selected from hydrogen atoms and alkyl groups with 1-6 carbon atoms. R is2Represents a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. R1Can be reacted with NR2Forming a ring structure. )
Specific examples of the N-vinylcarboxylic acid amide include N-vinylformamide, N-vinylacetamide, N-vinylpropionamide, N-vinylbenzamide, N-vinyl-N-methylformamide, N-vinyl-N-ethylformamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, and N-vinylpyrrolidone. Among them, N-vinylacetamide is particularly preferable. The N-vinylcarboxylic acid amides may be used singly or in combination of two or more.
The polymer used in the present invention may be a homopolymer of N-vinylcarboxylic acid amide, but may be a copolymer containing other monomer units in the structure.
The other monomer unit is not particularly limited as long as it can copolymerize with the N-vinylcarboxylic acid amide, and examples thereof include monomer units derived from: unsaturated carboxylic acid monomers such as methacrylic acid, itaconic acid, maleic anhydride, crotonic acid, and salts and esters of derivatives thereof;
acryloyl morpholine, isopropyl acrylamide;
unsaturated nitrile monomers such as methacrylonitrile and α -chloroacrylonitrile;
ethylenically unsaturated monomers containing a linear or branched alkyl group, such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, t-butyl methacrylate, pentyl (meth) acrylate, heptyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, and tetradecyl (meth) acrylate;
alicyclic alkyl group-containing ethylenically unsaturated monomers such as cyclohexyl (meth) acrylate and isobornyl (meth) acrylate;
ethylenically unsaturated monomers containing a fluorinated alkyl group such as trifluoroethyl (meth) acrylate and heptadecafluorodecyl (meth) acrylate; (meth) acrylamide, N-methoxymethyl- (meth) acrylamide, N-ethoxymethyl- (meth) acrylamide, N-propoxymethyl- (meth) acrylamide, N-butoxymethyl- (meth) acrylamide, N-pentoxymethyl- (meth) acrylamide, N-bis (methoxymethyl) acrylamide, N-ethoxymethyl-N-methoxymethyl methacrylamide, N-bis (ethoxymethyl) acrylamide, N-ethoxymethyl-N-propoxymethyl methacrylamide, N-bis (propoxymethyl) acrylamide, N-butoxymethyl-N- (propoxymethyl) methacrylamide, N-ethoxymethyl-N- (propoxymethyl) methacrylamide, N-ethoxymethyl-N- (propoxymethyl) acrylamide, N-ethoxymethyl-N- (meth) acrylamide, N-propoxymethyl-N-ethoxymethyl-acrylamide, N-ethoxymethyl-N-propoxymethyl-acrylamide, N-ethoxymethyl-acrylamide, N-N-ethoxymethyl-N-propoxymethyl-N-propoxymethyl-acrylamide, N-N-propoxymethyl-N-propoxymethyl-acrylamide, N-propoxymethyl-N-, Amide group-containing ethylenically unsaturated monomers such as N, N-bis (butoxymethyl) acrylamide, N-butoxymethyl-N- (methoxymethyl) methacrylamide, N-bis (pentyloxymethyl) acrylamide, N-methoxymethyl-N- (pentyloxymethyl) methacrylamide, N-dimethylaminopropyl acrylamide, N-diethylaminopropyl acrylamide, N-dimethylacrylamide, and N, N-diethylacrylamide;
hydroxyl group-containing ethylenically unsaturated monomers such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyvinylbenzene, 1-ethynyl-1-cyclohexanol, and allyl alcohol; styrene, alpha-methylstyrene, o-methylstyrene, p-methylstyrene, m-methylstyrene, vinylnaphthalene, benzyl acrylate, benzyl methacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol acrylate, phenoxydiethylene glycol methacrylate, phenoxytetraethylene glycol acrylate, phenoxytetraethylene glycol methacrylate, phenoxyhexaethylene glycol acrylate, phenoxyhexaethylene glycol methacrylate, phenyl acrylate, phenyl methacrylate, etc,
When crosslinking is required, it is derived from 2- [ (O-1' -methylpropylideneamino) carboxyamino ] ethyl methacrylate (カレンズ MOI-BM (registered trademark) manufactured by Showa Denko K.K.), 2- [ (3, 5-dimethylpyrazolyl) carbonylamino ] ethyl methacrylate (カレンズ MOI-BP (registered trademark) manufactured by Showa Denko K.K.), (dihydroxypropyl meth) acrylate, trade names ライトエステル HO, ライトエステル HOP, ライトエステル HOB, ライトエステル HOA, ライトエステル HOPA manufactured by Kyowa Denshi chemical Co., Ltd., and trade name ライトアクリレート (registered trademark) HOBA manufactured by Kyowa Kagaku K.K., Ltd.).
The content of the monomer unit derived from the N-vinylcarboxylic acid amide in the copolymer is preferably 60 mol% or more and 100 mol% or less.
Among these, homopolymers of N-vinylacetamide are excellent in the reduction in film thickness when an aqueous solution compounding agent is applied to various substrates, and are most preferable as a coating material for secondary batteries having a high level of safety requirement from the viewpoint of heat resistance.
The weight average molecular weight of the N-vinylcarboxylic acid amide polymer used in the present invention is preferably 1 to 400 million, more preferably 10 to 300 million, and still more preferably 50 to 200 million. The weight average molecular weight herein is determined by a method using GPC measurement described later.
Further, the viscosity of an aqueous solution obtained by dissolving the polymer in water to 5 mass% is preferably 1,000 to 30,000 mPas, more preferably 3,000 to 20,000 mPas, and still more preferably 6,000 to 15,000 mPas. The viscosity is determined by a brookfield viscometer described later.
An aqueous solution of a polymer having such characteristics becomes a viscous liquid having thixotropy and slidability.
The method for producing the polymer is not particularly limited, and the polymer can be produced by polymerizing various monomers of the N-vinylcarboxylic acid amide by a known polymerization method using a radical polymerization initiator. Examples of the polymerization method include a solution polymerization method, an aqueous solution polymerization method, a precipitation polymerization method, and a reversed-phase suspension polymerization method. When the polymerization is completed, a product in the form of a viscous liquid, agar or powder is obtained. Further, the viscous liquid or agar-like product can be powdered by dehydration and drying.
In the case of application to coating, since it is necessary to increase the molecular weight, a radical polymerization method in an aqueous solution is preferable.
In the case of carrying out the polymerization reaction by the aqueous solution polymerization method, the aqueous monomer solution is fed into a reaction tank equipped with a stirrer, a thermometer and a nitrogen aeration tube, and nitrogen aeration of the aqueous monomer solution is carried out. Then, if a radical polymerization initiator is added and mixed, polymerization is started. The aqueous monomer solution is prepared by dissolving various monomers such as N-vinylcarboxylic acid amide and unsaturated carboxylic acid monomer in ion-exchanged water in advance and adjusting the temperature to the polymerization initiation temperature. The radical polymerization initiator is preferably charged at a temperature of 45 to 70 ℃ and can be produced by successive polymerization by dropping an aqueous monomer solution or an aqueous polymerization initiator solution.
In the case of a polymerization method in which all the monomers are charged in advance, the temperature inside the polymerization vessel rises to a peak temperature about 0.5 to 3 hours after the initiator is charged.
The concentration of the N-vinylcarboxylic acid amide monomer in the aqueous monomer solution is preferably 3 to 20 mass%, more preferably 5 to 15 mass%, and still more preferably 7 to 12 mass%, and when the concentration of the monomer in the aqueous monomer solution is within this range, the polymerization rate and the degree of heat generation are suitable, and a substance having a desired viscosity can be obtained, and can be easily taken out from the reaction tank.
As the polymerization initiator used for the polymerization of the N-vinylcarboxylic acid amide, a polymerization initiator generally used in radical polymerization of vinyl compounds can be used without limitation. Examples thereof include redox polymerization initiators, azo compound polymerization initiators, and peroxide polymerization initiators.
These may be used alone in 1 kind, or may be used in combination of 2 or more kinds. In some cases, the molecular weight can be adjusted by using a chain transfer agent.
Examples of the redox polymerization initiator include a combination of ammonium persulfate and sodium thiosulfate, sodium hydrogen thiosulfate, trimethylamine, or tetramethylethylenediamine, and a combination of tert-butyl hydroperoxide and sodium thiosulfate or sodium hydrogen thiosulfate.
Examples of the peroxide-based polymerization initiator include organic peroxides such as persulfates of sodium, potassium, and ammonium, benzoyl peroxide, lauroyl peroxide, caproyl peroxide, t-butyl peroxide (2-ethylhexanoate), and diacetyl peroxide.
Examples of azo initiators include 2,2 ' -azobis (2-methylbutyronitrile), 2 ' -azobis (2, 4-dimethylvaleronitrile), dimethyl-2, 2 ' -azobis (isobutyrate), dimethyl-2, 2 ' -azobis (2-methylbutyrate) and dimethyl-2, 2 ' -azobis (2, 4-dimethylvalerate), azo compounds such as 2,2 '-azobis (2-amidinopropane) dihydrochloride, 2' -azobis [ N- (2-carboxyethyl) -2-methylpropionamidine ] N hydrate, 2 '-azobis {2- [ N- (2-carboxyethyl) amidino ] propane } N hydrate, and dimethyl 2, 2' -azobis (2-methylpropionate).
Among the polymerization initiators mentioned above, in the polymerization method using water as a solvent, 2' -azobis [ N- (carboxyethyl) -2-methylpropionamidine ] tetrahydrate (trade name: Fuji フイルム and azo polymerization initiator VA-057 made by opto-pure Chinese Co., Ltd.) containing no halogen is most preferably used in consideration of the influence of the residue on the polymer.
This VA-057 was dissolved in water degassed with nitrogen and used.
These radical polymerization initiators may be used in combination, and polymerization is also possible by using a redox polymerization initiator in combination with a water-soluble azo compound polymerization initiator.
In this case, a combination of ammonium persulfate and sodium thiosulfate is preferably used as the redox polymerization initiator, and 2, 2' -azobis (2-amidinopropane) dihydrochloride is preferably used as the water-soluble azo compound polymerization initiator.
The amount of the radical polymerization initiator to be used is preferably 100 to 10000 ppm by mass, more preferably 500 to 5000 ppm by mass in the case of the azo compound type polymerization initiator, and preferably 10 to 300 ppm by mass, more preferably 30 to 100 ppm by mass in the case of the redox type polymerization initiator, based on the total amount of all monomers. If the amount of the radical polymerization initiator used is within the above range, both the polymerization rate and the molecular weight of the copolymer tend to be suitable.
As long as the range in which the object of the present invention is not impaired, a chain transfer agent may be used in the polymerization for the purpose of adjusting the degree of polymerization of the polymer and introducing a modifying group into the terminal of the polymer. Examples of the chain transfer agent include aldehyde compounds such as propionaldehyde, ketone compounds such as acetone and methyl ethyl ketone, thiol compounds such as 2-hydroxyethanethiol, 3-mercaptopropionic acid, dodecanethiol and thioacetic acid, halogenated hydrocarbon compounds such as carbon tetrachloride, trichloroethylene and tetrachloroethylene, and phosphinate salts such as sodium phosphinate monohydrate. Among them, thiol compounds, aldehyde compounds and ketone compounds are suitably used. The amount of the chain transfer agent added is preferably 0.1 mass% or more and 2.0 mass% or less with respect to the total amount of all monomers. When the amount is within this range, the polymerization degree can be sufficiently adjusted, and the purpose of introducing a modifying group into the terminal of the polymer can be sufficiently achieved.
Polysaccharides
The polysaccharide is not particularly limited as long as it is hydrophilic, and xanthan gum, gellan gum, pectin, carrageenan, guar gum, karaya gum, dextrin, cellulose derivatives, and the like can be used. Among these, cellulose derivatives are preferable in terms of high heat resistance.
The cellulose derivative is also not particularly limited, and the following can be used. Specifically, methylcellulose, hydroxypropylmethylcellulose, alkali (earth) metal salts of carboxymethylcellulose, hydroxyethylcellulose, hydroxyethylmethylcellulose, and the like can be used. As the alkali (earth) metal salt, sodium salt, potassium salt, lithium salt, magnesium salt, calcium salt, and the like are used.
Water (W)
The water is not particularly limited, and distilled water, ion-exchanged water, tap water, and the like can be used, but ion-exchanged water is preferable.
Composition for aqueous coating liquid
The composition for an aqueous coating solution of the present invention is a composition in which the polymer of N-vinylcarboxylic acid amide and polysaccharide are dissolved in a solvent containing at least water.
The method for mixing the polymer of N-vinylcarboxylic acid amide and the polysaccharide is not particularly limited, and in order to obtain a more uniform mixed state, it is preferable to dissolve the polymer of N-vinylcarboxylic acid amide and the polysaccharide in a solvent containing at least water, and then mix them with other compounding agents as necessary. Further, it is more preferable to dissolve both the polymer of N-vinylcarboxylic acid amide and the polysaccharide in a solvent containing at least water, and then to mix and homogenize the solution. This makes it possible to obtain an ideal mixture form. As the solvent, water may be used, but a mixed solvent of water and alcohols may be used. When alcohols are mixed, the alcohols are preferably contained in the solvent in an amount of 50% by mass or less. It is preferable to use only water from the viewpoints of cost, production control, waste disposal, and the like.
The preferable mixture form is a state in which polysaccharides such as cellulose derivatives are finely dispersed in a water-soluble polymer which is a polymer of N-vinylcarboxylic acid amide, and it is presumed that a part of hydrogen bonds between the polymer of N-vinylcarboxylic acid amide and water are inhibited, and as a result, it is considered that water is easily kept away and drying is easily performed.
In order to obtain this effect, an effect can be expected when the amount of one component is small compared to the mixed state at the same ratio, and in the present invention, the effect is easily exhibited when the amount of the polysaccharide is small compared to the polymer of N-vinylcarboxylic acid amide.
For the above reasons, the ratio of the polymer of N-vinylcarboxylic acid amide to the polysaccharide is preferably 95: 5-30: 70, more preferably 95: 5-50: 50, more preferably 90: 10-80: 20. the mixing ratio corresponds to the composition ratio.
When the amount is within this range, a composition having excellent drying easiness can be obtained. The term "easy-drying property" means that, for example, the polymer of N-vinylcarboxylic acid amide can be dried in a shorter time than the drying time of the polymer when the same heat is applied. If the drying time is short, the time for applying heat is short, and the time until cooling may be short. Therefore, the thermal history of the substrate and the like can be reduced.
The concentration of the N-vinylcarboxylic acid amide polymer in the composition is appropriately selected depending on the use of the composition, the coating method, the viscosity of the coating liquid, and the like, but it is generally desirable to be in the range of preferably 1 to 30 mass%, more preferably 2 to 20 mass%, and still more preferably 4 to 15 mass% with respect to the total weight of the composition containing the solvent containing at least water. If the amount is within this range, the coating can be performed by a known printing method, and the drying can be performed quickly.
The content of the polysaccharide in the composition is appropriately selected depending on the application in which the composition is used, the coating method, the viscosity of the coating liquid, and the like, but is generally desirably in the range of preferably 0.05% by mass or more and 10% by mass or less, more preferably in the range of 0.1% by mass or more and 5% by mass or less, and further preferably in the range of 0.2% by mass or more and 3% by mass or less, relative to the total weight of the composition including the solvent containing at least water. When the content is within this range, the drying acceleration effect of the composition can be exerted.
The composition of the present invention may further contain an inorganic filler. When the inorganic filler is contained, the surface area is increased, and the filler itself has heat radiation property, so that the drying property can be further improved. With respect to the composition containing an inorganic filler, the coated product itself has high heat dissipation properties, heat resistance, and toughness, and thus has very great industrial advantages.
The inorganic filler includes at least 1 selected from boron nitride, aluminum nitride, silicon carbide, silica, alumina, boehmite, talc, zinc oxide, titanium black, and graphite, and among these, alumina is preferable in terms of heat dissipation, easy availability, and the like.
The content of the inorganic filler is preferably 70% by mass or less, more preferably 20 to 60% by mass, and still more preferably 30 to 55% by mass, based on the total weight of the composition. When the content is within this range, the drying acceleration effect of the composition can be exerted.
The method for producing an aqueous polymer coating material according to the present invention is a method for producing a coating material by applying the composition for an aqueous coating liquid to a surface of a substrate and drying the composition to form a coating film. The composition is as described above.
In other words, in the present invention, by mixing a predetermined amount of the polysaccharide in the composition containing at least water of the polymer of N-vinylcarboxylic acid amide, it is possible to provide a coating/drying method in which the drying time is significantly shortened as compared with a composition containing no polysaccharide.
The method of applying the composition to the substrate is not particularly limited, and continuous coating using a roll-to-roll pattern coating apparatus is also possible, except for spray coating, roll coating, bar coating, gravure coating, die coating, knife coating, inkjet coating, brush coating, dip coating, and the like.
The composition may further contain a known material added to the coating material, for example, an emulsion-based binder, a thixotropic agent, a dispersing agent, a surface conditioner, an antifoaming agent, and a leveling agent, in addition to the above.
As the substrate, a film, a nonwoven fabric, a porous body, a plate-like body, or the like can be used without particular limitation.
Examples of the material constituting the base material include homopolypropylene, a copolymer of propylene and another olefin, polyethylene terephthalate, polyethylene naphthalate, polyamide ether ketone, polyimide, polyamide, polyphenylene sulfone, polyphenylene ether, polyethylene, polyether sulfone, polyether ether ketone, polybenzimidazole, polyether imide, polyamide imide, and poly (p-phenylene 2, 6-benzobisimide)
Azole), fluorine resin, an organic resin material such as an epoxy resin, a metal material such as aluminum, copper, silver, or iron, glass (silicon oxide), aluminum oxide, magnesium oxide, aluminum nitride, aluminum carbide, silicon nitride, barium titanate, or the like. The base material can be used alone, can also be combined with more than 2.
The drying method is not particularly limited, and is not particularly limited to spin drying, vacuum drying, warm air drying, infrared drying, and the like.
The drying time is also not particularly limited, but according to the present invention, the drying time can be shortened at a rate of 1/3 to 1/10 in terms of 95% by mass drying time as described later, as compared with the case where the polymer of N-vinylacetamide is dried alone.
Examples
The present invention will be described below with reference to examples, but the present invention is not to be construed as being limited thereto.
[ production example ]
Polymerization of N-vinylacetamide
A4-neck 1-liter separable flask was equipped with a nitrogen vent tube, a stirrer, a solvent dropping device, and a thermometer, 550g of ion-exchanged water was charged into the separable flask, and 50g of N-vinylacetamide (available from Showa Denko K.K.) was charged into the separable flask. In this state, the polymerization initiation temperature was raised to 51 ℃ by heating with stirring while replacing nitrogen in the solution, and 0.04g (hereinafter, VA-057) of 2, 2' -azobis [ N- (carboxyethyl) -2-methylpropionamidine ] tetrahydrate (total monomer ratio: 0.08% by mass) as an initiator was charged in a state of being dissolved in 10g of ion-exchanged water degassed with nitrogen. After 4 hours of polymerization reaction in this state, the internal temperature was raised to 80 ℃ and held for 1 hour, then a sample was taken, the residual monomer was measured by HPLC, and the reaction was terminated when the monomer content became 1000 mass ppm or less, and then 400g of ion-exchanged water was added, diluted and stirred for 1 hour, followed by cooling.
In addition, the weight average molecular weight of the obtained N-vinylacetamide polymer was 2,000,000. The viscosity of the 5 mass% aqueous solution was 11,500 mPas.
Determination of weight average molecular weight
The polymer was dissolved in distilled water at a concentration of 1% by mass and the weight average molecular weight was measured by GPC (gel permeation chromatography) under the following conditions.
In addition, for the calculation of the weight average molecular weight in the present measurement, a calibration curve prepared from the results of the absolute molecular weight measurement of the N-vinylacetamide polymer of each molecular weight band was used.
Detector (RI): SHODEX (registered trademark) RI-201H manufactured by SHOWA DENKO K.K
A pump: LC-20AD manufactured by Shimadzu corporation
Column oven: SHODEX (registered trademark) AO-30C manufactured by SHOWA DENKO K.K
An analysis device: SIC 480II Deta Station manufactured by システムインスツルメンツ K.K
Column: SHODEX (registered trademark) SB 806X 2 manufactured by SHOWA DENKO K.K
Eluent: distilled water/2-propanol 8/2 (mass ratio)
Flow rate: 0.7ml/min
Viscosity measurement method
The test piece was placed in a 300ml beaker of a tall form and allowed to stand in a thermostatic bath at 20 ℃ for 12 hours or longer, thereby forming a state completely free from internal bubbles. Then, the temperature of the test piece was confirmed to be 20. + -. 0.5 ℃ by a thermometer in a beaker placed in a constant temperature water tank adjusted to 20 ℃ and the viscosity was measured under the following conditions using a type B viscometer shown in JIS K-7117-1-1999. The viscosity after 10 minutes after the value stabilized was recorded.
Viscometer: model HA DVE (Brookfield) viscometer
A rotor: no.6 rotor
Rotating speed: 50rpm
Temperature: 20 deg.C
Determination of the amount of residual monomers
A sample of the polymer was dissolved in sodium sulfate (Na) at a concentration of 0.05mol/L2SO4) Aqueous solution to obtain polymer solution. The concentration of the polymer in the polymer solution was 0.1% by mass. The polymer solution was analyzed by GPC to calculate the total amount of each monomer (residual monomer amount) remaining in the polymer sample. The completion of the polymerization reaction can be confirmed by the amount of the residual monomer.
Detector (RI): SHODEX (registered trademark) UV-41, manufactured by SHOWA DENKO K.K
A pump: SHODEX (registered trademark) DS-4, SHODEX, SHOWA DENKAGE
Column oven: スガイ U-62040 deg.C
An analysis device: C-R7A Plus manufactured by Shimadzu corporation
Column: showa Denko K.K. Shodex (registered trademark) SB802.5HQ X1
Eluent: 0.05mol/L Na2SO4The flow rate of the aqueous solution was 1.0ml/min
The concentration was determined by a calibration curve method (sample concentration: 1,5, 10, 100 mass ppm).
[ examples 1 to 16]
An aqueous solution of a 5 mass% N-vinylacetamide polymer obtained in production example and a 5 mass% aqueous solution of polysaccharides shown in Table 1 were stirred and homogenized at 25 ℃ in the same vessel at the mixing ratio shown in Table 1 to prepare a composition for an aqueous coating solution. In example 16, alumina was mixed at a ratio shown in table 1 after homogenization.
[ comparative examples 1 to 7]
Compositions for aqueous coating solutions having the compositions shown in table 1 were prepared. In comparative example 7, alumina was mixed in the aqueous solution of comparative example 1 at the ratio shown in table 1.
In addition, materials other than the polymer of N-vinylacetamide (PNVA) used in examples and comparative examples are as follows.
Sodium salt of carboxymethyl cellulose (CMC): MAC-350-HC Japanese paper (Kabushiki Kaisha)
Acrylic emulsion: ビニブラン (registered trademark) 2685 Nixin chemical industry Co., Ltd
Styrene butadiene latex: BM-400B Japanese ゼオン strain
Guar gum: chemical preparation of pure reagent
Hydroxyethyl cellulose (HEC): AW-15F Sumitomo refinement (strain)
Alumina: AL-160SG Zhaohe electrician (strain)
The drying rate was measured by the following method.
Evaluation (95% by mass drying time and 47.5% by mass drying time)
The aqueous coating liquid composition of the sample was charged into an aluminum cup in an amount of 1.5g, and spread smoothly and uniformly on the bottom surface of the aluminum cup with a spatula. The samples of examples 1 to 15 and comparative examples 1 to 6 were subjected to measurement of a 95 mass% decrease from the initial mass thereof, i.e., the evaporation time until water substantially evaporated, at 85 ℃ for 1 minute by using a thermobalance (PM 460, manufactured by メトラー & トレド Co.).
With respect to examples 1 to 15, the difference in evaporation time (shortening time) from comparative example 1 in which no polysaccharide was added was obtained.
In example 16 and comparative example 7, the evaporation time from the initial mass reduction of 47.5 mass% at 85 ℃ was evaluated. In example 16, the difference in evaporation time from comparative example 7 was set as a shortened time.
The results are shown in table 1.
From the results in Table 1, it was found that a drying time comparable to that of an acrylic emulsion or a styrene butadiene latex having a high drying rate was obtained by adding and mixing a polysaccharide such as CMC to a polymer of N-vinylacetamide. It is also found that the drying property can be most improved when the ratio of the polysaccharide to the polymer of N-vinylacetamide is about 10 to 20% by mass.
Further, the mixing of the polymer of N-vinylacetamide and the polysaccharide is a useful means for increasing the drying rate, because the drying rate is faster in the case of the mixing of the polymer of N-vinylacetamide and the polysaccharide according to the ratio, and the drying rate is faster in the case of the mixing of the polysaccharide to the system to which the inorganic filler is added, as compared with the case of the polysaccharide alone, which does not contain the polymer of N-vinylcarboxylic acid amide.
As described above, by adding and mixing a polysaccharide such as CMC at a certain ratio to the polymer of N-vinylcarboxylic acid amide, the drying rate can be increased.
In the production of a product having a step of coating an aqueous coating solution containing a polymer of N-vinylcarboxylic acid amide and drying the coating solution, the present invention is expected to allow drying at a higher speed, and to contribute significantly to the improvement of productivity of the entire industry.
Claims (8)
1. A composition for an aqueous coating liquid, comprising at least a polymer of an N-vinylcarboxylic acid amide, a polysaccharide and water,
the polymer of N-vinylcarboxylic acid amide is a homopolymer of N-vinylcarboxylic acid amide,
the composition ratio of the polymer of the N-vinylcarboxylic acid amide to the polysaccharide is 90: 10-80: 20,
the polymer of the N-vinyl carboxylic acid amide is dissolved in the composition.
2. The composition for aqueous coating solutions according to claim 1, wherein the N-vinylcarboxylic acid amide is N-vinylacetamide.
3. The composition for aqueous coating solutions according to claim 1, wherein the polysaccharide is a cellulose derivative.
4. The composition for aqueous coating solutions according to claim 3, wherein the cellulose derivative is an alkali metal salt of carboxymethyl cellulose or an alkaline earth metal salt of carboxymethyl cellulose.
5. The composition for aqueous coating solutions according to any one of claims 1 to 4, further comprising an inorganic filler.
6. The composition for aqueous coating solutions according to claim 5, wherein the inorganic filler is alumina.
7. The composition for an aqueous coating solution according to any one of claims 1 to 4, wherein the content of the polymer of N-vinylcarboxylic acid amide in the composition is in the range of 0.05 to 20% by mass.
8. A method for producing an aqueous polymer coating material, comprising applying the composition for an aqueous coating solution according to any one of claims 1 to 7 to the surface of a substrate and drying the composition.
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| JP2018199227 | 2018-10-23 | ||
| JP2018-199227 | 2018-10-23 | ||
| PCT/JP2019/040225 WO2020085123A1 (en) | 2018-10-23 | 2019-10-11 | Composition for aqueous coating liquid containing n-vinylcarboxylic acid amide polymer |
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| JPWO2022059678A1 (en) * | 2020-09-17 | 2022-03-24 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2015153529A (en) * | 2014-02-12 | 2015-08-24 | 日本ゼオン株式会社 | Binder composition for lithium ion secondary battery electrode, slurry composition for lithium ion secondary battery positive electrode, positive electrode for lithium ion secondary battery, and lithium ion secondary battery |
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| JPS5433149Y2 (en) | 1973-12-10 | 1979-10-13 | ||
| JPH06170327A (en) | 1992-12-03 | 1994-06-21 | Tsuneo Tate | Drying method of coating material |
| JP3397365B2 (en) * | 1993-04-01 | 2003-04-14 | キヤノン株式会社 | Ink, ink manufacturing method, ink jet recording method, recording unit, ink cartridge, and ink jet recording apparatus |
| JPH09221623A (en) * | 1996-02-16 | 1997-08-26 | Showa Denko Kk | Antifouling protective layer-forming composition |
| DE19851024A1 (en) * | 1998-11-05 | 2000-05-11 | Basf Ag | Aqueous dispersions of water-soluble polymers of N-vinylcarboxamides, processes for their preparation and their use |
| JP2001164170A (en) * | 1999-12-09 | 2001-06-19 | Tombow Pencil Co Ltd | Metalescent aqueous ink composition for ball-point pen |
| JP2001202964A (en) * | 2000-01-20 | 2001-07-27 | Hitachi Maxell Ltd | Alkaline battery |
| JP2001202953A (en) * | 2000-01-21 | 2001-07-27 | Hitachi Maxell Ltd | Production method of nickel paste electrode |
| JP2001202952A (en) * | 2000-01-21 | 2001-07-27 | Hitachi Maxell Ltd | Method of producing paste-form nickel electrode |
| JP2001216969A (en) * | 2000-02-03 | 2001-08-10 | Hitachi Maxell Ltd | Paste hydrogen storage alloy electrode and nickel- hydrogen battery |
| JP2002088297A (en) * | 2000-09-11 | 2002-03-27 | Showa Denko Kk | Surface protective material |
| JP2002201397A (en) * | 2000-12-27 | 2002-07-19 | Pentel Corp | Aqueous ink for ball-point pen |
| JP3736842B2 (en) * | 2001-01-10 | 2006-01-18 | 日立マクセル株式会社 | Electrode for alkaline electrolyte battery and alkaline electrolyte battery using the same |
| JP4870287B2 (en) * | 2001-09-05 | 2012-02-08 | 株式会社サクラクレパス | Ink composition for ballpoint pen and water-based ballpoint pen using the composition |
| JP2009102606A (en) | 2007-10-01 | 2009-05-14 | Aica Kogyo Co Ltd | Adhesive composition and bonding method |
| US8771859B2 (en) * | 2009-03-13 | 2014-07-08 | Hitachi Maxell, Ltd. | Separator for battery and nonaqueous electrolyte battery using same |
| JP5743032B1 (en) * | 2014-01-27 | 2015-07-01 | 住友化学株式会社 | Coating liquid and laminated porous film |
| WO2015146649A1 (en) | 2014-03-24 | 2015-10-01 | 昭和電工株式会社 | Slurry for positive electrode of lithium ion secondary cell, positive electrode obtained using said slurry, method for manufacturing said positive electrode, lithium ion secondary cell formed using said positive electrode, and method for manufacturing said cell |
| JP6494273B2 (en) * | 2014-12-22 | 2019-04-03 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | Non-aqueous electrolyte secondary battery electrode winding element, non-aqueous electrolyte secondary battery using the same, and non-aqueous electrolyte secondary battery electrode winding element manufacturing method |
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