JP2005097518A

JP2005097518A - マイクロカプセル化顔料及びその製造方法、水性分散液、並びに、インクジェット記録用インク

マイクロカプセル化顔料及びその製造方法、水性分散液、並びに、インクジェット記録用インク Download PDF

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Publication number: JP2005097518A
Authority: JP; Japan
Prior art keywords: group; pigment; hydrophilic; ink; polymerizable
Prior art date: 2003-02-26
Legal status : Withdrawn

Application number

JP2004052239A

Other languages

English (en)

Japanese (ja)

Other versions

JP2005097518A5 (enExample

Inventor

Toshiyuki Miyabayashi

利行宮林

Current Assignee

Seiko Epson Corp

Original Assignee

Seiko Epson Corp

Priority date

2003-02-26

Filing date

2004-02-26

Publication date

2005-04-14

2004-02-26 Application filed by Seiko Epson Corp filed Critical Seiko Epson Corp

2004-02-26 Priority to JP2004052239A priority Critical patent/JP2005097518A/ja

2005-04-14 Publication of JP2005097518A publication Critical patent/JP2005097518A/ja

2005-10-27 Publication of JP2005097518A5 publication Critical patent/JP2005097518A5/ja

Status Withdrawn legal-status Critical Current

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239000000049 pigment Substances 0.000 title claims abstract description 738
239000006185 dispersion Substances 0.000 title claims abstract description 247
238000004519 manufacturing process Methods 0.000 title claims abstract description 70
239000002245 particle Substances 0.000 claims abstract description 426
229920000642 polymer Polymers 0.000 claims abstract description 173
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 121
238000006116 polymerization reaction Methods 0.000 claims abstract description 88
238000000034 method Methods 0.000 claims abstract description 76
239000004094 surface-active agent Substances 0.000 claims description 309
125000000129 anionic group Chemical group 0.000 claims description 169
239000000178 monomer Substances 0.000 claims description 130
-1 methacryloyl group Chemical group 0.000 claims description 118
125000002091 cationic group Chemical group 0.000 claims description 77
239000003505 polymerization initiator Substances 0.000 claims description 67
125000001165 hydrophobic group Chemical group 0.000 claims description 66
230000002209 hydrophobic effect Effects 0.000 claims description 61
239000003999 initiator Substances 0.000 claims description 58
125000004432 carbon atom Chemical group C* 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 35
239000003960 organic solvent Substances 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 31
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 26
239000007787 solid Substances 0.000 claims description 25
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
125000000542 sulfonic acid group Chemical group 0.000 claims description 21
239000004064 cosurfactant Substances 0.000 claims description 19
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 18
125000000626 sulfinic acid group Chemical group 0.000 claims description 18
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 17
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 17
238000000746 purification Methods 0.000 claims description 17
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 15
239000012860 organic pigment Substances 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
239000000080 wetting agent Substances 0.000 claims description 15
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125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 14
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 14
235000011187 glycerol Nutrition 0.000 claims description 14
238000002156 mixing Methods 0.000 claims description 14
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 14
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
125000006539 C12 alkyl group Chemical group [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])* 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
150000005215 alkyl ethers Chemical class 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
238000009835 boiling Methods 0.000 claims description 12
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238000007720 emulsion polymerization reaction Methods 0.000 claims description 11
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125000002843 carboxylic acid group Chemical group 0.000 claims description 9
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238000010526 radical polymerization reaction Methods 0.000 claims description 9
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239000003431 cross linking reagent Substances 0.000 claims description 7
230000003213 activating effect Effects 0.000 claims description 6
125000002723 alicyclic group Chemical group 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000003368 amide group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
150000001720 carbohydrates Chemical class 0.000 claims description 6
239000000839 emulsion Substances 0.000 claims description 5
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
239000012190 activator Substances 0.000 claims description 3
238000007334 copolymerization reaction Methods 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 3
238000011161 development Methods 0.000 abstract description 6
238000010556 emulsion polymerization method Methods 0.000 abstract description 4
239000000976 ink Substances 0.000 description 302
239000012736 aqueous medium Substances 0.000 description 67
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125000000751 azo group Chemical group [*]N=N[*] 0.000 description 58
239000000203 mixture Substances 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 42
239000003795 chemical substances by application Substances 0.000 description 41
239000002609 medium Substances 0.000 description 32
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239000003086 colorant Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 30
238000003756 stirring Methods 0.000 description 29
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
230000000052 comparative effect Effects 0.000 description 27
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238000011156 evaluation Methods 0.000 description 19
239000000243 solution Substances 0.000 description 18
238000010992 reflux Methods 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
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USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 15
239000007864 aqueous solution Substances 0.000 description 14
239000011324 bead Substances 0.000 description 14
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AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 13
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 12
239000002253 acid Substances 0.000 description 11
150000002430 hydrocarbons Chemical group 0.000 description 11
238000005299 abrasion Methods 0.000 description 10
AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 10
230000009477 glass transition Effects 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
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238000000108 ultra-filtration Methods 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
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COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 8
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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239000001052 yellow pigment Substances 0.000 description 8
229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 7
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NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
KZFDTCQVSIKDRH-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CN(C)CCCCl KZFDTCQVSIKDRH-UHFFFAOYSA-N 0.000 description 6
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