JP5802596B2 - 電気泳動用(メタ)アクリル酸エステル系着色樹脂粒子及びその製造方法 - Google Patents
電気泳動用(メタ)アクリル酸エステル系着色樹脂粒子及びその製造方法 Download PDFInfo
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- JP5802596B2 JP5802596B2 JP2012081340A JP2012081340A JP5802596B2 JP 5802596 B2 JP5802596 B2 JP 5802596B2 JP 2012081340 A JP2012081340 A JP 2012081340A JP 2012081340 A JP2012081340 A JP 2012081340A JP 5802596 B2 JP5802596 B2 JP 5802596B2
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- ALBJGICXDBJZGK-UHFFFAOYSA-N [1-[(1-acetyloxy-1-phenylethyl)diazenyl]-1-phenylethyl] acetate Chemical compound C=1C=CC=CC=1C(C)(OC(=O)C)N=NC(C)(OC(C)=O)C1=CC=CC=C1 ALBJGICXDBJZGK-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
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- INAHAJYZKVIDIZ-UHFFFAOYSA-N boron carbide Chemical compound B12B3B4C32B41 INAHAJYZKVIDIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 238000007865 diluting Methods 0.000 description 1
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- 238000012674 dispersion polymerization Methods 0.000 description 1
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- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- AEOQMMHATQYSLZ-UHFFFAOYSA-N ethenyl ethenesulfonate Chemical compound C=COS(=O)(=O)C=C AEOQMMHATQYSLZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000005357 flat glass Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- ZARXZEARBRXKMO-UHFFFAOYSA-N n,n-bis(ethenyl)aniline Chemical compound C=CN(C=C)C1=CC=CC=C1 ZARXZEARBRXKMO-UHFFFAOYSA-N 0.000 description 1
- XMGREXCXPFEQPM-UHFFFAOYSA-N n,n-dimethyl-2-(2-phenylethenoxy)ethanamine Chemical compound CN(C)CCOC=CC1=CC=CC=C1 XMGREXCXPFEQPM-UHFFFAOYSA-N 0.000 description 1
- SDYRIBONPHEWCT-UHFFFAOYSA-N n,n-dimethyl-2-phenylethenamine Chemical compound CN(C)C=CC1=CC=CC=C1 SDYRIBONPHEWCT-UHFFFAOYSA-N 0.000 description 1
- VXSULRYWTMNNON-UHFFFAOYSA-N n-(4-phenylbut-3-enyl)aniline Chemical compound C=1C=CC=CC=1NCCC=CC1=CC=CC=C1 VXSULRYWTMNNON-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- BUYFKEVRYFERNS-UHFFFAOYSA-N n-methyl-4-phenylbut-3-en-1-amine Chemical compound CNCCC=CC1=CC=CC=C1 BUYFKEVRYFERNS-UHFFFAOYSA-N 0.000 description 1
- CGIORIVBAHKXQZ-UHFFFAOYSA-N n-phenyl-n-(4-phenylbut-3-enyl)aniline Chemical compound C=1C=CC=CC=1C=CCCN(C=1C=CC=CC=1)C1=CC=CC=C1 CGIORIVBAHKXQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000004079 stearyl 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])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
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- XGFPOHQJFNFBKA-UHFFFAOYSA-B tetraaluminum;phosphonato phosphate Chemical compound [Al+3].[Al+3].[Al+3].[Al+3].[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O XGFPOHQJFNFBKA-UHFFFAOYSA-B 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- OMSYGYSPFZQFFP-UHFFFAOYSA-J zinc pyrophosphate Chemical compound [Zn+2].[Zn+2].[O-]P([O-])(=O)OP([O-])([O-])=O OMSYGYSPFZQFFP-UHFFFAOYSA-J 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
前記電子供与基を有する化合物が、アクリル酸のアミノアルキルエステル及びスチレンのアミノアルキルエステルから選択され、かつ0.0308〜0.00333の前記顔料に対する質量含有比で含まれることを特徴とする電気泳動用(メタ)アクリル酸エステル系着色樹脂粒子が提供される。
本発明の単量体組成物は、炭素数8〜26のアルキル基を有する(メタ)アクリル酸エステル系単量体を少なくとも1種類以上含むビニル系単量体、電子供与基を有する化合物及び顔料を少なくとも含む。このため、単量体組成物を重合して得られる着色樹脂粒子は非極性溶媒中での分散性及び異なる帯電極性を有する粒子との凝集抑制に優れる。
本発明の単量体組成物は、炭素数8〜26のアルキル基を有する(メタ)アクリル酸エステル系単量体を少なくとも一種類以上含むビニル系単量体を含有する。また、所望の物性に影響を与えない限りその他の単量体成分を含んでいてもよい。
本発明の単量体組成物は電子供与基を有する化合物を含む。このような化合物を含むため、着色樹脂粒子は電気泳動用の樹脂粒子として好適に使用することができる。また、電子供与基としてはアミノ基、アミノアルキル基、ピリジル基のような複素環基、又は4級アンモニウム塩等の基を挙げることができる。
本発明の単量体組成物は顔料を含む。このため、着色樹脂粒子及びそれを含む分散液は外観に優れる。
着色樹脂粒子を得る方法としては、公知の重合方法、例えば懸濁重合法、乳化重合法、分散重合法等を挙げることができる。
本発明の着色樹脂粒子は、0.9〜1.04g/cm3の真密度を有する。ここで、真密度とは、物質自身が占める体積だけを密度算定用の体積とする密度のことをいう。
得られる着色樹脂粒子は非極性溶媒中での分散性及び異なる帯電極性を有する粒子との凝集抑制に優れるため、このような特性が求められる、画像表示用素子、電気粘性流体用粒子等の粒子の電気泳動を利用する用途、静電潜像トナー用粒子の用途にこれらを好適に使用することができる。
純水30gと重合開始剤1gを100mLビーカーに入れ、25℃で3時間攪拌する。攪拌後、ろ過を行い未溶解の重合開始剤を濾別し、得られた濾液(A)を20g採取し、25℃の真空乾燥機で24時間乾燥する。残存した開始剤の量(B)を計測し、水に対する溶解度を算出する。
水に対する溶解度 (質量%)=100×B(g)/A(g)
島津製作所−マイクロメリティックス社製 乾式密度計アキュピック1330(気体置換法)を用い、着色樹脂粒子4gを10ccセルに採り、繰り返し5回以上測定し、その平均値を求める。
シリコーンオイル(信越化学社製:KF−96L−1CS、動粘度:1センチストークス)にスチレン10質量部、シリコーンマクロモノマー(サイラプレーンFM−0721、チッソ社製)90質量部を重合して得られる分散剤を溶解させ、0.04質量%シリコーンオイルを作成する。この溶液に得られた着色樹脂粒子を加え、固形分10質量%の着色樹脂粒子の分散液(約3mL)を調製し、測定用試料とする。次いで、片面に酸化インジウムスズ(ITO)をコートしたガラス板(幅20mm、長さ100mm、厚み0.7mm、松浪硝子工業社製、商品名:ITOコートガラス EAGLE XG)2枚を用意する。図1に示すように、一方のガラス基板のコート面にスペーサーとして厚み50μmのテフロン(登録商標)フィルム(幅20mm、長さ25mm)を貼り付け、2枚のガラス板をコート面が内側になるようにした状態でスペーサーを介して挟み込んだ平行平板(冶具)とする。2枚のガラス板の酸化インジウムスズ(ITO)のコート面のすき間(幅25mm、長さ20mm、厚み100μm)に、シリンジを用いて、予め調製しておいた測定用試料を毛細管現象により浸透させる。次に、冶具の両面を測定装置(KEITHLEY社製、商品名:KEITHLEY6514)に接続し、+20Vの電圧を30秒間印加させて得られた測定値を帯電量[nC]とする。
帯電密度[nC・g/m2(nC/(m2/g))]
=帯電量[nC]/1g当たりの粒子の比表面積(m2/g)
・1gあたりの粒子の比表面積[m2/g]=6÷(密度×粒子径)
サイラプレーンFM−0711(チッソ社製)82質量部、イソステアリルアクリレート6質量部及びグリシジルメタクリレート2質量部を、ジメチルシリコーンオイル(信越シリコーン社製KF−96L 2cs)110質量部と混合し、重合開始剤としてアゾビスバレロニトリル(和光純薬製:V−65)を0.07質量部添加して、58℃、13時間、重合を実施し、エポキシ基をもった反応性シリコーン系高分子A(反応性分散剤)を作製する。重量平均分子量は70万である。そして、ジメチルシリコーンオイル(信越シリコーン社製KF−96L 2cs)で希釈することで反応性シリコーン系高分子の10質量%シリコーンオイル溶液を作製する。
(1)シアン粒子及び白色粒子、着色樹脂粒子がそれぞれ正極、負極に駆動しており、目視による混色が見られない場合・・・混色なし(合格(○))
(2)シアン粒子及び白色粒子どちらか一方ないし両方において、両極板に着色樹脂粒子若しくはシアン粒子又は白色粒子が駆動しており、目視による混色が見られる場合・・・混色あり(不合格(×))
と判定する。
シリコーンオイル中における着色樹脂粒子の分散安定性評価については、次の方法により行う。実施例、比較例に記載の着色樹脂粒子を量り取り、そこへ着色樹脂粒子固形分が10質量%となるようにシリコーンオイル(動粘度:10センチストークス、KF−96L−10CS、信越化学社製)を加えて着色樹脂粒子を分散させ、これを測定用試料とする。測定用試料50mLを50mLメスシリンダーに移し、静置48時間経過後の着色樹脂粒子の分散状態を観察し、下記2段階の評価基準を基に評価する。
○:着色樹脂粒子の沈殿が若干見られるものの、無色透明な上澄み部分が40%未満
×:着色樹脂粒子が沈殿しており、無色透明な上澄み部分が40%以上
と判定する。
着色樹脂粒子の平均粒子径の測定方法は、Coulter Electronics Limited発行のReference MANUAL FOR THE COULTER MULTISIZER(1987)に従って、粒子サイズに適した細孔径サイズを有するアパチャーを用いてキャリブレーションを行う方法とする。使用するアパチャーの細孔径サイズは、平均粒子径が1〜10μm未満の着色樹脂粒子に対しては50μmを、平均粒子径が10〜30μm未満の着色樹脂粒子に対しては100μmのものを用いる。
変動係数(CV値)とは、標準偏差(σ)及び上記平均粒子径(Y)から以下の式により算出された値である。
CV値(%)=(σ/Y)×100
攪拌機のついたフラスコにシリコーンオイル(KF−96L−1CS、信越化学社製)100質量部と、予め開始剤として2,2'−アゾビス−(2,4−ジメチルバレロニトリル)2質量部を溶解したジエチルアミノエチルメタクリレート7質量部、シリコーンマクロモノマー(サイラプレーンFM−0725、チッソ社製)95質量部及びα−メチルスチレンダイマー(ノフマーMSD、日本油脂社製)0.5質量部を添加し、窒素雰囲気下70℃にて撹拌を行いながら20時間溶液重合を行い、反応物(A)を得た。
非極性溶媒としてのジルコニアビーズ(直径5mm)500質量部を入れた300mLガラス製ビーズポットに酢酸エチル60質量部、PT−501R(石原産業社製、酸化チタン、一次粒子径:180nm)50質量部と顔料分散剤(日本ルブリゾール社製 商品名:ソルスパース28000)5.0質量部を添加し、室温にて24時間ビーズミルによる顔料分散を行った。得られた顔料分散液0.6質量部に、酢酸エチル3.5質量部、モディパーFS700(日油社製シリコーン−アクリル系ブロック共重合体)0.8質量部を酢酸エチル6質量部に溶解した溶液、及びデュラネートTPA−100(旭化成ケミカル社製、ヘキサメチレンジイソシアネートのイソシアヌレート型ポリイソシアネート)0.12質量部をそれぞれ加え、顔料が分散した混合物を調製した。50mLの容量のガラス瓶にイソパラフィン(出光興産社製 商品名 IPソルベント2028)25質量部を入れ、超音波ホモジイナイザー(SONIFIER 450,BRANSON社製)を用いて攪拌しながら、前記混合物を滴下しながら添加した。添加後、得られた混合物を引き続いて10分間、乳化分散に付して乳化液を得た。
アクリル酸イソステアリル(以下、ISTAとも称する)200質量部、顔料10質量部を直径5mmのジルコニアビーズの入ったビーズポッドに入れ6時間攪拌し、顔料を分散した。次に前記混合液の一部を計り取り、残りのISTA並びにエチレングリコールジメタクリレート(以下、EGDMAとも称する)を添加してISTA/EGDMA/DEAEMA/顔料=71.6/15.0/0.4/13.0(質量%)とした単量体組成物を調製した。
実施例2〜5及び比較例1〜6として、モノマー/架橋剤/電子供与基含有化合物/顔料/顔料分散剤の各配合組成を変更した他は、実施例1と同条件とし、得られた着色樹脂粒子の測定と評価を行った。これらの結果について、上述の実施例1とともに表1にまとめて示す。なお、実施例5は参考例である。
(1)ISTAはアクリル酸イソステアリルを、
(2)MMAはメタクリル酸メチルを、
(3)IOCAはアクリル酸イソオクチル
(4)EGDMAはエチレングリコールジメタクリレートを、
(5)DEAEMAはジエチルアミノエチルメタクリレートを、
(6)4−VPyは4−ビニルピリジン(シグマアルドリッチ社製)を、
(7)顔料Rは商品名クロモファインレッド6605T(大日精化工業社製)を、
(8)顔料Yは商品名Fast Yellow 7416(山陽色素社製)を、
(9)ABNVは2,2’−アゾビス(2,4−ジメチルバレロニトリル)を、
(10)OTAZO−15は1,1’−アゾビス(1−アセトキシ−1−フェニルエタン)を、
(11)V601はジメチル2,2’−アゾビス(2−メチルプロピオネート)を、そして
(12)DVBはジビニルベンゼンをそれぞれ意味する。
Claims (3)
- 炭素数8〜26のアルキル基を有する(メタ)アクリル酸エステル系単量体を少なくとも1種類以上含むビニル系単量体50〜98質量%、電子供与基を有する化合物0.01〜0.4質量%、及び顔料を含む単量体組成物を重合して得られ、0.9〜1.04g/cm3の真密度及び0.5〜3.5nC・g/m2の帯電密度を有し、
前記電子供与基を有する化合物が、アクリル酸のアミノアルキルエステル及びスチレンのアミノアルキルエステルから選択され、かつ0.0308〜0.00333の前記顔料に対する質量含有比で含まれることを特徴とする電気泳動用(メタ)アクリル酸エステル系着色樹脂粒子。 - 請求項1に記載の電気泳動用(メタ)アクリル酸エステル系着色樹脂粒子の製造方法であって、
炭素数8〜26のアルキル基を有する(メタ)アクリル酸エステル系単量体を少なくとも1種類以上含むビニル系単量体50〜98質量%、電子供与基を有する化合物0.01〜0.4質量%、及び顔料を含む単量体組成物に、重合開始剤として水に対する溶解度が0.25質量%未満のアゾ系重合開始剤のみが混合された混合物を重合させる工程を含む電気泳動用(メタ)アクリル酸エステル系着色樹脂粒子の製造方法。 - 前記アゾ系重合開始剤が、前記単量体組成物100質量部に対して0.05〜10質量部の割合で混合される請求項2に記載の方法。
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