WO2016104803A1 - Dispersant - Google Patents
Dispersant Download PDFInfo
- Publication number
- WO2016104803A1 WO2016104803A1 PCT/JP2015/086440 JP2015086440W WO2016104803A1 WO 2016104803 A1 WO2016104803 A1 WO 2016104803A1 JP 2015086440 W JP2015086440 W JP 2015086440W WO 2016104803 A1 WO2016104803 A1 WO 2016104803A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
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- group
- carbon atoms
- formula
- dispersant
- Prior art date
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 207
- 239000006185 dispersion Substances 0.000 claims abstract description 200
- 239000000049 pigment Substances 0.000 claims abstract description 191
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- -1 quaternary ammonium salt compound Chemical class 0.000 claims abstract description 119
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 238000004519 manufacturing process Methods 0.000 claims abstract description 56
- 238000004040 coloring Methods 0.000 claims abstract description 46
- 229920000768 polyamine Polymers 0.000 claims abstract description 43
- 239000003960 organic solvent Substances 0.000 claims abstract description 35
- 239000012860 organic pigment Substances 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 132
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 26
- 150000001450 anions Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 230000008030 elimination Effects 0.000 claims description 7
- 238000003379 elimination reaction Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 22
- 125000001033 ether group Chemical group 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 85
- 239000002245 particle Substances 0.000 abstract description 45
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 121
- 150000002430 hydrocarbons Chemical group 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 49
- 230000015572 biosynthetic process Effects 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 41
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 33
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 29
- 239000011248 coating agent Substances 0.000 description 26
- 238000000576 coating method Methods 0.000 description 26
- 238000005259 measurement Methods 0.000 description 26
- 239000000758 substrate Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 24
- 125000003277 amino group Chemical group 0.000 description 20
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 19
- 229920000728 polyester Chemical group 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 17
- 125000003438 dodecyl 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 description 17
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 15
- 229940089960 chloroacetate Drugs 0.000 description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000011521 glass Substances 0.000 description 13
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 12
- 125000002704 decyl 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])* 0.000 description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 125000002347 octyl 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])[H] 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 125000001117 oleyl 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])=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])[H] 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 description 6
- 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 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 102100034003 FAU ubiquitin-like and ribosomal protein S30 Human genes 0.000 description 5
- 101000732045 Homo sapiens FAU ubiquitin-like and ribosomal protein S30 Proteins 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 238000007664 blowing Methods 0.000 description 5
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000011164 primary particle Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 150000008051 alkyl sulfates Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 125000001421 myristyl 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])[H] 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 125000000913 palmityl 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])[H] 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical group O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- MVSBPSPKVXSVIG-UHFFFAOYSA-N 3-[3-(2,5-dioxopyrrol-3-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=C(C=CC=2)C=2C(NC(=O)C=2)=O)=C1 MVSBPSPKVXSVIG-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910002482 Cu–Ni Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
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- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- SKCNNQDRNPQEFU-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]-n,n,n'-trimethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)CCCN(C)C SKCNNQDRNPQEFU-UHFFFAOYSA-N 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RRLOOYQHUHGIRJ-UHFFFAOYSA-M sodium;ethyl sulfate Chemical compound [Na+].CCOS([O-])(=O)=O RRLOOYQHUHGIRJ-UHFFFAOYSA-M 0.000 description 1
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
Definitions
- the present invention relates to a dispersant, a pigment dispersion for a color filter, a coloring composition for a color filter, a color filter using the same, and a quaternary ammonium salt compound.
- a color filter used in a liquid crystal display device is a photolithography method in which a coloring composition in which a resin or the like is blended with the non-aqueous pigment dispersion is applied to a transparent substrate such as glass, and then exposed, cured, developed, and thermally cured. Etc. are manufactured.
- a coloring composition in which a resin or the like is blended with the non-aqueous pigment dispersion is applied to a transparent substrate such as glass, and then exposed, cured, developed, and thermally cured. Etc. are manufactured.
- dispersants in oil used for the production of non-aqueous pigment dispersions polymer dispersants such as graft polymers are known, and in order to satisfy various required performances, improvements to the dispersants are being studied. .
- Patent Document 1 discloses an alkoxy polyalkylene glycol having a small average particle diameter, a low viscosity, excellent storage stability, and good redispersibility for a color filter pigment dispersion.
- a pigment dispersion for a color filter is described which contains a pigment dispersant, an organic pigment, and an ether organic solvent having a group and a quaternary ammonium group and having a specific structure.
- Patent Document 2 for the purpose of providing a colored radiation-sensitive composition capable of forming a pixel having a forward tapered shape and excellent solvent resistance even with a low exposure amount, a colorant, Light containing alkali-soluble resin, polyfunctional monomer having caprolactone structure, and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one A colored radiation composition containing a polymerization initiator is described.
- Patent Document 3 discloses that a large amount of pigment can be dispersed finely and uniformly even when only a small amount of a dispersant is used, and has excellent plate-making characteristics, high color density even when thin, good surface smoothness, and impurities.
- a pigment, a pigment dispersant comprising a specific molecular structure and a copolymer containing an acidic functional group and a polyester chain, and an acidic functional group
- a colored resist comprising a copolymer having a molecular structure in which a structural unit having a structural unit and a photocurable functional group, and a structural unit having an SP value of 10 or more and not containing an acidic functional group, and an organic solvent
- Pigment dispersions and photosensitive coloring compositions are described.
- a color filter is described which is formed by curing the photosensitive coloring composition for the purpose of realizing a high color reliability and a wide color gamut.
- the pigment is further miniaturized in order to improve the contrast.
- the particles such as pigments are made finer, the cohesive force between the particles is increased, so that the particles are aggregated in the dispersion and the particle size is increased. Therefore, the storage stability of the dispersion containing fine particles tends to decrease.
- studies have been made to improve the dispersion characteristics by using a dispersing agent into which an adsorbing group excellent in adsorption to the particle surface, such as pigment, and a dispersing group excellent in affinity to a solvent are introduced.
- the present invention provides a pigment dispersion and a color filter pigment for obtaining a pigment dispersion and a coloring composition having a small average particle size, low viscosity, excellent storage stability, and excellent developability and heat resistance. It is an object to provide a dispersion, a coloring composition for a color filter, a color filter using the same, and a quaternary ammonium salt compound.
- the present inventors have found that the above-mentioned problems can be solved by using a dispersant having a structural unit A represented by the formula (A) and having a specific structure in a dispersion of particles such as pigments. . That is, the present invention relates to the following [1] to [5]. [1] A dispersant having a structural unit A represented by the formula (A) in the molecular structure and having an average number of structural units A contained in one molecular structure of 1.0 or more and 22.0 or less.
- R x1 represents an alkanediyl group having 2 to 12 carbon atoms
- R x2 represents a hydrocarbon group having 1 to 18 carbon atoms
- a represents an average addition mole number
- R 4 represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms
- R 6 represents an alkanediyl group having 1 to 4 carbon atoms
- (M 1 ) ⁇ represents an anion.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different.
- Step 1 A pigment dispersion for a color filter containing the dispersant according to [1], an organic pigment, and an organic solvent.
- Step 1 A color filter manufactured using the coloring composition for a color filter according to [2].
- Step 1 Formula (B) in the molecular structure: [Wherein, R 4 may be the same or different and represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group, and R 5 represents one or more carbon atoms. 18 or less alkanediyl groups are shown.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different.
- a quaternary ammonium salt compound represented by the formula (1) [In the formula, R x1 represents an alkanediyl group having 2 to 12 carbon atoms, R x2 represents a hydrocarbon group having 1 to 18 carbon atoms, a represents an average addition mole number, and 2 to 100 R y1 represents an alkanediyl group having 2 to 4 carbon atoms, R y2 represents a hydrocarbon group having 1 to 18 carbon atoms, d represents an average addition mole number, and is 1 to 100.
- R 1 , R 2 and R 4 may be the same or different, each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group, and R 3 represents hydrogen And at least one selected from a hydrocarbon group having 1 to 10 carbon atoms in which a part of atoms and hydrogen atoms may be substituted with a hydroxyl group, and R 5 represents an alkanediyl group having 1 to 18 carbon atoms (provided that the R 5 is a single bond which is adjacent to R 1 Indicates to), R 6 represents a 1 to 4 alkanediyl group having a carbon number, (M 1) - and (M 2) - each independently represent an anion, n, p, m, and k is the average Indicates the number of structural units, (n + p + m + k) is 1.0 or more and 22.0 or less, (n + p) is 1.0 or more and 22.0 or less, n is
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average structure thereof is represented by n, p, m, or k. Each structural unit in which the number of units is shown may be in any arrangement order. ]
- a dispersant for obtaining a pigment dispersion and a colored composition having a small average particle size, low viscosity, excellent storage stability, and excellent heat resistance a pigment dispersion for a color filter, A colored composition for a color filter, a color filter using the same, and a quaternary ammonium salt compound can be provided.
- the dispersant of the present invention has a structural unit A represented by the formula (A) in the molecular structure (hereinafter also simply referred to as “structural unit A”), and the average of the structural units A contained in one molecular structure.
- the number is 1.0 or more and 22.0 or less.
- the dispersant of the present invention is suitable as a dispersant for obtaining a pigment dispersion and a color composition having a small average particle size, low viscosity, excellent storage stability, and excellent heat resistance in the process of producing a color filter. It is. The reason is not clear, but it can be considered as follows.
- the dispersant of the present invention has a polyester chain having a high affinity for an organic solvent and a quaternary ammonium group capable of maintaining a strong adsorptivity on the pigment surface for a long period of time.
- the polyester chain in the compound of the present invention spreads in the organic solvent, so that a strong repulsive force is generated between the organic pigment particles in the pigment dispersion. Arise. Therefore, it is considered that aggregation of pigments can be effectively suppressed, and the viscosity of the pigment dispersion can be kept low.
- the quaternary ammonium group is strongly adsorbed on the surface of the organic pigment and maintains its strong adsorptivity for a long time. Therefore, it is considered that the dispersant of the present invention is hardly detached from the pigment surface despite having high affinity for the solvent. Therefore, the dispersant of the present invention is excellent in finely pulverizing the pigment at the time of dispersion. It is considered that excellent dispersibility is maintained.
- the dispersant of the present invention is a polymer compound, the number of quaternary ammonium groups per molecule (that is, the number of structural units A) is small and can be precisely controlled.
- the pigment dispersion for a color filter of the present invention has a small average particle diameter, a low viscosity, and excellent storage stability. Furthermore, since the interaction of the polyester chain of the dispersant of the present invention is enhanced by removing the organic solvent, for example, when the dispersant of the present invention is used for the color filter coloring composition, the solvent removal during coating film formation, In the course of development processing such as exposure, a pseudo-crosslinked structure is formed in the coating film.
- the dispersant of the present invention has the structural unit A represented by the formula (A) in the molecular structure, and the average number of structural units A contained in one molecular structure is 1.0 or more and 22.0 or less.
- R x1 represents an alkanediyl group having 2 to 12 carbon atoms
- R x2 represents a hydrocarbon group having 1 to 18 carbon atoms
- a represents an average addition mole number
- R 4 represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms
- R 6 represents an alkanediyl group having 1 to 4 carbon atoms
- (M 1 ) ⁇ represents an anion.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different.
- the average number of structural units A contained in one molecular structure of the dispersant is 1.0 or more, preferably 1.5 or more.
- it is 1.8 or more, and from the same viewpoint, it is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0.
- it is more preferably 3.0 or less.
- the number of carbon atoms of R x1 is 2 or more, preferably 3 or more, more preferably from the viewpoint of improving the dispersibility and storage stability of the dispersion, the developability of the coloring composition, and the heat resistance. 4 or more, more preferably 5 or more, and from the same viewpoint, it is 12 or less, preferably 10 or less, more preferably 7 or less, still more preferably 6 or less, still more preferably 5 or less.
- R x1 include at least one selected from an ethylene group, various propanediyl groups, various butanediyl groups, various pentanediyl groups, various hexanediyl groups, and various heptanediyl groups.
- Dispersibility and storage stability of the dispersion From the viewpoint of improving the colorability, the developability of the colored composition, and the heat resistance, preferably a butane-1,4-diyl group, a pentane-1,5-diyl group and a hexane-1,6-diyl group And at least one selected from the group consisting of pentane-1,5-diyl groups.
- a is 2 or more from the viewpoint of improving the dispersibility and storage stability of the dispersion, the developability of the coloring composition, and the heat resistance, and is preferably 10 or more, more preferably 15 or more. From the same viewpoint, it is 100 or less, preferably 70 or less, more preferably 50 or less, and further preferably 30 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and when two or more [(C ⁇ O) R x1 O] are present, the arrangement thereof is either random or block There may be.
- [(C ⁇ O) R x1 O] is a structural unit derived from ⁇ -caprolactone, and ⁇ -valero, from the viewpoint of the affinity of the dispersant with the organic solvent and the developability and heat resistance of the coloring composition. It is preferable to include at least one selected from structural units derived from lactones, and it is more preferable to include structural units derived from ⁇ -caprolactone.
- the carbon number of R x2 is 1 or more from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 6 or more, more preferably 10 or more, and 18 or less from the same viewpoint, Preferably it is 16 or less, More preferably, it is 14 or less.
- R x2 is preferably at least one selected from an aliphatic hydrocarbon group and a hydrocarbon group having an aromatic ring, more preferably an aliphatic hydrocarbon group, from the viewpoint of improving the dispersibility and storage stability of the dispersion. More preferred is at least one selected from an alkyl group and an alkenyl group, and more preferred is an alkyl group.
- R x2 includes, for example, a methyl group, an ethyl group, an octyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, an oleyl group, a stearyl group, a phenyl group, a p-octylphenyl group, and a p-nonylphenyl group. From the viewpoint of improving the dispersibility and storage stability of the dispersion, at least one selected from a methyl group, an octyl group, a decyl group, a lauryl group, an oleyl group, and a stearyl group is preferable.
- it is at least one selected from a methyl group, an octyl group, a decyl group, and a lauryl group, more preferably at least one selected from an octyl group and a lauryl group, and still more preferably a lauryl group.
- the carbon number of R 4 is 10 or less, preferably 4 or less, more preferably 2 or less, and preferably 1 or more. Preferably it is 1.
- R 4 is preferably a hydrocarbon group not substituted with a hydroxyl group. Specific examples of R 4 include at least one selected from a methyl group, an ethyl group, various propyl groups, and various butyl groups, and preferably at least one selected from a methyl group and an ethyl group, More preferably, it is a methyl group.
- the carbon number of the alkanediyl group of R 5 is 1 or more, preferably 2 or more, more preferably 3 or more. From the viewpoint of improvement, it is 18 or less, preferably 14 or less, more preferably 10 or less, and still more preferably 6 or less.
- the alkanediyl group of R 5 include at least one selected from an ethylene group, various propanediyl groups, various hexanediyl groups, and various nonanediyl groups, and a viewpoint of improving the dispersibility and storage stability of the dispersion.
- At least one selected from a propane-1,3-diyl group, a hexane-1,6-diyl group, and a nonane-1,9-diyl group more preferably a propane-1,3-diyl group and At least one selected from hexane-1,6-diyl groups.
- the number of carbon atoms of R 6 is 4 or less, preferably 3 or less, more preferably 2 or less, and preferably 1 or more, more preferably, from the viewpoint of ease of production of the dispersant of the present invention.
- R 6 is preferably a methylene group.
- (M 1 ) ⁇ is an anion, and is preferably a halide ion, an alkyl sulfate ion, an alkylbenzene sulfone from the viewpoint of improving the ease of production of the dispersant of the present invention and the dispersibility and storage stability of the dispersion.
- At least one selected from acid ions and alkyl carbonate ions, more preferably halide ions, more preferably at least one selected from chloride ions, bromide ions, and iodide ions, and more preferably chloride ions. is there.
- the dispersant of the present invention further includes, in one molecular structure, a structural unit B represented by the formula (B) (hereinafter also simply referred to as “structural unit B”) and a structural unit represented by the formula (C). It may have at least one selected from C (hereinafter also simply referred to as “structural unit C”).
- R 4 and R 5 are the same as those described in formula (A), and R 3 is a hydrogen atom and part of the hydrogen atoms may be substituted with a hydroxyl group of 1 or more carbon atoms. It represents at least one selected from 10 or less hydrocarbon groups, and (M 2 ) ⁇ represents an anion. ]
- R 3 is preferably at least one selected from a hydrogen atom and a hydrocarbon group having 1 to 10 carbon atoms from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of improving the dispersibility and storage stability of the dispersion, the carbon number of the hydrocarbon group of R 3 is 10 or less, preferably 7 or less, more preferably 4 or less, and even more preferably 2 or less. And it is one or more.
- R 3 includes at least one selected from a hydrogen atom, a methyl group, an ethyl group, a propyl group, and a benzyl group. From the viewpoint of improving the dispersibility and storage stability of the dispersion, a hydrogen atom and a methyl group are preferable. It is at least one selected from the group.
- (M 2 ) ⁇ is an anion, and examples thereof include carboxylate ions, sulfonate ions, halide ions, sulfate ions, nitrate ions, nitrite ions, phosphate ions, phosphate ions, and carbonate ions.
- the ions may have a substituent such as a hydrocarbon group.
- (M 2 ) ⁇ is preferably a carboxylate ion, a halide ion, an alkyl sulfate ion, and from the viewpoint of improving the ease of production of the dispersant of the present invention and the dispersibility and storage stability of the dispersion. It is at least one selected from alkylbenzene sulfonate ions.
- the carboxylate ion is preferably an acetate ion.
- the halide ion is preferably at least one selected from chloride ion, bromide ion and iodide ion, and more preferably chloride ion.
- the alkyl sulfate ion is preferably at least one selected from methyl sulfate ions and ethyl sulfate ions, and more preferably methyl sulfate ions.
- the alkylbenzene sulfonate ion is preferably p-toluene sulfonate ion.
- (M 2 ) ⁇ is more preferably at least one selected from acetate ions, chloride ions, methylsulfate ions, and p-toluenesulfonate ions from the above viewpoint.
- Preferred examples of the R 4 and R 5 alkanediyl groups in the formula (B) and the formula (C) are the same as those in the above formula (A).
- the dispersant of the present invention preferably further has a structural unit D represented by the formula (D) in the molecular structure (hereinafter also simply referred to as “structural unit D”).
- structural unit D represents a structural unit D represented by the formula (D) in the molecular structure (hereinafter also simply referred to as “structural unit D”).
- R y1 represents an alkanediyl group having 2 to 4 carbon atoms
- R y2 represents a hydrocarbon group having 1 to 18 carbon atoms
- d represents an average addition mole number, and 1 to 100 inclusive.
- R 4 , R 5 , R 6 , (M 1 ) ⁇ are the same as those described in the formula (A).
- [R y1 O] may be the same or different when there are a plurality of [R y1 O]. ]
- the average number of structural units D contained in one molecular structure of the dispersant is preferably 0.3 or more, more preferably 0.5. From the same viewpoint, it is preferably 11.0 or less, preferably 5.5 or less, more preferably 3.5 or less, and further preferably 0.6 or more, more preferably 0.8 or more. Preferably it is 2.5 or less, More preferably, it is 2.0 or less, More preferably, it is 1.5 or less, More preferably, it is 1.0 or less, More preferably, it is 0.8 or less.
- the number of carbon atoms in R y1 is preferably 4 or less, more preferably 3 or less, and preferably 2 or more from the viewpoints of dispersibility and storage stability.
- R y1 is preferably at least one selected from an ethylene group and a propylene group.
- d is preferably 1 or more, more preferably 15 or more, still more preferably 21 or more, still more preferably 30 or more, still more preferably 40 or more, and preferably 100 Or less, more preferably 95 or less, still more preferably 70 or less, and still more preferably 50 or less.
- (R y1 O) d is preferably a structural unit represented by the following formula ( Da ) from the viewpoints of dispersibility and storage stability.
- PO represents a structural unit derived from propylene oxide
- EO represents a structural unit derived from ethylene oxide
- d1 and d2 represent the average number of added moles
- d1 is 0 or more and 100 or less
- d2 is 0 or more and 100 or less
- d1 + d2 is 1 or more and 100 or less
- * represents a binding site.
- the structural unit is preferably a block polymer, more preferably a diblock polymer, and the (PO) terminal side of the formula (Da) is R y2 It is preferably bonded to O and the (EO) terminal side is preferably bonded to a carbonyl group.
- d1 is preferably 11 or more, more preferably 15 or more, still more preferably 21 or more, still more preferably 25 or more from the viewpoints of dispersibility and storage stability, and from the viewpoint of dispersibility and manufacturability, Preferably it is 60 or less, More preferably, it is 50 or less, More preferably, it is 35 or less.
- d2 is preferably 1 or more, more preferably 5 or more, still more preferably 11 or more, and even more preferably 13 or more. From the viewpoint of solubility, it is preferably 95 or less, more preferably 70 or less, still more preferably 50 or less, still more preferably 30 or less, and still more preferably 20 or less.
- the total of d1 and d2 (d1 + d2) is preferably 15 or more, more preferably 21 or more, more preferably 30 or more, still more preferably 40 or more, preferably 95 or less, from the viewpoints of dispersibility and storage stability. More preferably, it is 70 or less, More preferably, it is 50 or less.
- the ratio of d1 to the sum of d1 and d2 is preferably 0.20 or more, more preferably 0.40 or more, and still more preferably 0.50 from the viewpoints of dispersibility and storage stability. From the viewpoint of dispersibility and manufacturability, it is preferably 0.97 or less, more preferably 0.86 or less, and still more preferably 0.80 or less.
- the carbon number of R y2 is preferably 1 or more, more preferably 6 or more, and still more preferably 10 or more from the viewpoints of dispersibility and redispersibility, and preferably 18 or less from the viewpoint of dispersibility and storage stability. More preferably, it is 16 or less, More preferably, it is 14 or less, More preferably, it is 12 or less.
- R y2 is preferably at least one selected from an aliphatic hydrocarbon group and an aromatic hydrocarbon group which may have an aliphatic hydrocarbon group, from the viewpoints of dispersibility and storage stability.
- a hydrogen group is more preferable, and at least one selected from an alkyl group and an alkenyl group is still more preferable.
- R y2 is at least one selected from a methyl group, an ethyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, an oleyl group, a stearyl group, a phenyl group, a p-octylphenyl group, and a p-nonylphenyl group.
- it is at least one selected from a methyl group, an ethyl group, a decyl group, a lauryl group, a myristyl group, a cetyl group, an oleyl group, a stearyl group, and a phenyl group, and more preferably a methyl group, At least one selected from a decyl group, a lauryl group, and a phenyl group, and from the viewpoint of redispersibility, preferably at least one selected from a phenyl group, a decyl group, and a lauryl group, dispersibility and storage stability In view of the above, it is preferably at least one selected from a methyl group, a decyl group, and a lauryl group, and has excellent dispersion From the viewpoint of storage stability and redispersibility, more preferably decyl group or a lauryl group, more preferably a lauryl group.
- the dispersant of the present invention preferably has an arrangement structure including one or more structural units A, and more preferably, the structural unit A, optionally the structural unit B, the structural unit C, and the structural unit D in one molecular structure. Having a sequence structure including at least one selected from the above, more preferably having a sequence structure including at least one selected from the structural unit A, optionally the structural unit B and the structural unit C in one molecular structure. More preferably, the single molecular structure has an array structure including at least one selected from the structural unit A and the structural unit D, optionally the structural unit B and the structural unit C.
- the total average number of structural units A, structural units B, structural units C and structural units D in a single molecular structure is preferably from the viewpoint of improving the dispersibility and storage stability of the dispersion. 22.0 or less, more preferably 11.0 or less, still more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0 or less, and even more preferably 3.0 or less. In view of the above, it is 1.0 or more, preferably 1.5 or more, more preferably 1.8 or more.
- the terminal of the sequence structure is preferably a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group, more preferably a hydrocarbon group having 1 to 10 carbon atoms and a carbon number. At least one selected from hydroxyalkyl groups having 2 to 6 carbon atoms, more preferably at least one selected from hydrocarbon groups having 1 to 5 carbon atoms and hydroxyalkyl groups having 3 to 6 carbon atoms, more preferably carbon. It is at least one selected from a hydrocarbon group having 1 to 3 carbon atoms and a hydroxyalkyl group having 4 to 6 carbon atoms.
- terminal refers to a terminal group that is bonded to N atoms at both ends of an array structure including one or more structural units A.
- the terminal means a terminal group bonded to the N atom of the structural unit represented by the structural unit A, the structural unit B, the structural unit C, or the structural unit D.
- An example of the above preferred terminal group is TR 5 — (T is a terminal atom or a substituent) at the R 5 side terminal.
- the weight average molecular weight Mw of the dispersant is preferably 2,000 or more, more preferably 3,000 or more, and still more preferably 3,500 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. Preferably, it is 50,000 or less, More preferably, it is 25,000 or less, More preferably, it is 20,000 or less, More preferably, it is 15,000 or less.
- the measuring method of a weight average molecular weight is based on the method as described in an Example.
- the dispersant of the present invention is preferably a dispersant made of a compound represented by the formula (1).
- R x1 , R x2 , a, R 4 , R 6 and (M 1 ) ⁇ are the same as those in formula (A), and R y1 , R y2 and d are the same as those in formula (D).
- R 3 and (M 2 ) ⁇ are the same as those in formula (C)
- R 1 and R 2 may be the same or different, and a part of the hydrogen atoms are substituted with hydroxyl groups.
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms (where R 5 adjacent to R 1 represents a single bond), n, p, m, and k represent the average number of structural units, (n + p + m + k) is 1.0 or more and 22.0 or less, (n + p) is 1.0 or more and 22.0 or less, and n is 0.8. 3 to 22.0, p is 0 to 11.0, m is 0 to 21.0, and k is 0 to 21. 0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average structure thereof is represented by n, p, m, or k. Each structural unit in which the number of units is shown may be in any arrangement order. ]
- (N + p + m + k) is 22.0 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11.0 or less, more preferably 7.0 or less, and still more preferably 5.0 or less. More preferably, it is 4.0 or less, More preferably, it is 3.0 or less, From the same viewpoint, it is 1.0 or more, Preferably it is 1.5 or more, More preferably, it is 1.8 or more.
- (N + p) is 22.0 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11.0 or less, more preferably 7.0 or less, and even more preferably 5.0 or less.
- n is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, and still more preferably. Is 4.0 or less, more preferably 3.0 or less. From the same viewpoint, 0.3 or more, preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.8 or more, Preferably it is 1.0 or more, More preferably, it is 1.5 or more, More preferably, it is 1.8 or more.
- p is 0 or more, and preferably 0.3 or more, more preferably 0.5 or more, still more preferably 0.6 or more, and still more preferably, from the viewpoint of improving the dispersibility and storage stability of the dispersion.
- m is 21.0 or less, preferably 4.0 or less, more preferably 2.0 or less, still more preferably 1.0 or less, and still more preferably. Is 0.5 or less, and is 0 or more from the same viewpoint.
- k is 21.0 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 4.0 or less, more preferably 2.0 or less, still more preferably 1.2 or less, From the same viewpoint, it is 0 or more.
- the ratio of (n + p) to (n + p + m + k) ((n + p) / (n + p + m + k)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the dispersant of the present invention, it is 1.0 or less, preferably 0.9 or less.
- the average number of structural units, n, p, m, k, (n + p + m + k) can be measured, for example, by the method described in the examples.
- Each structural unit whose average number of structural units is represented by n, p, m, and k may be in any arrangement order. When any one or more of n, p, m, and k is plural, each structural unit may be in any arrangement order such as random or block.
- the carbon number of R 1 and R 2 is 10 or less, preferably 8 or less, more preferably 6 or less, and even more preferably 1.
- R 1 and R 2 are preferably a hydrocarbon group not substituted with a hydroxyl group.
- R 1 and R 2 are preferably at least one selected from a hydrocarbon group having 1 to 10 carbon atoms and a hydroxyalkyl group having 2 to 6 carbon atoms, more preferably a hydrocarbon having 1 to 5 carbon atoms.
- At least one selected from a group and a hydroxyalkyl group having 3 to 6 carbon atoms is there.
- R 1 and R 2 include at least one selected from a methyl group, an ethyl group, a butyl group, a hexyl group, a hydroxymethyl group, a hydroxybutyl group, and a hydroxyhexyl group.
- a dispersant composed of a compound in which k in the formula (1) is 0, more specifically, from the compound represented by the formula (1a).
- a dispersant is preferred.
- R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 4 , R 5 , R 6 , (M 1 ) ⁇ , n, m and p are represented by the formula ( The same as described in 1), and (n + p + m) is 1.0 or more and 22.0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average number of structural units in n, p and m
- Each structural unit represented by may have any arrangement order.
- the ratio of (n + p) to (n + p + m) ((n + p) / (n + p + m)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the dispersant of the present invention, it is 1.0 or less.
- the dispersant of the present invention may be a mixture containing a compound represented by the formula (1 ′).
- a compound represented by the formula (1 ′) wherein R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ and (M 2 ) ⁇ are , Ni, pi, mi and ki represent the number of structural units, (ni + pi + mi + ki) is an integer from 1 to 22, and ni is an integer from 1 to 22. Yes, pi is an integer from 0 to 11, mi is an integer from 0 to 21, and ki is an integer from 0 to 21.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the structural unit is represented by ni, pi, mi, ki. Each structural unit whose number is shown may be in any arrangement order. ]
- (Ni + pi + mi + ki) is 22 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11 or less, more preferably 7 or less, still more preferably 5 or less, still more preferably 4 or less, and even more.
- it is 3 or less, and from the same viewpoint, it is 1 or more, preferably 2 or more.
- ni is 22 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11 or less, more preferably 7 or less, still more preferably 5 or less, still more preferably 4 or less, and still more preferably. 3 or less, and from the same viewpoint, it is 1 or more, preferably 2 or more.
- pi is 0 or more, preferably 1 or more from the viewpoint of improving the dispersibility and storage stability of the dispersion, and 11 or less, preferably 5 or less, more preferably 3 or less from the same viewpoint. More preferably, it is 2 or less, and more preferably 1. mi is 21 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 4 or less, more preferably 2 or less, more preferably 1 or less, and from the same viewpoint, 0 or more. Yes, even more preferably 0. ki is 21 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 4 or less, more preferably 2 or less, still more preferably 1 or less, and from the same viewpoint, 0 or more. is there.
- the ratio of (ni + pi) to (ni + pi + mi + ki) ((ni + pi) / (ni + pi + mi + ki)) is preferably 0.3 or more, more preferably from the viewpoint of dispersibility and storage stability of the dispersion containing the compound of the present invention. Is 0.6 or more, and is 1.0 or less, preferably 0.9 or less, from the viewpoint of ease of production of the compound of the present invention.
- Each structural unit whose number of structural units is indicated by ni, pi, mi, ki may be in any arrangement order. When one or more of ni, pi, mi, and ki are plural, each structural unit may have any arrangement order such as random or block.
- the dispersant is preferably a compound represented by the formula (1a ′).
- R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 4 , R 5 , R 6 and (M 1 ) ⁇ are those described in formula (1)
- Ni, pi, and mi are the same as those described in the formula (1 ′), and (ni + pi + mi) is an integer of 1 to 22.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the number of structural units is ni, pi, or mi.
- ni and mi in the formula (1a ′) are the same as the above-described range.
- the ratio of (ni + pi) to (ni + pi + mi) ((ni + pi) / (ni + pi + mi)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the compound of the present invention, it is 1.0 or less.
- the dispersant according to the first embodiment of the present invention is a dispersant composed of a compound having p of 0 in formula (1), more specifically a dispersant composed of a compound represented by formula (1-1). is there.
- R x1 , R x2 , a, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ , (M 2 ) ⁇ , m, and k are represented by the formula ( The same as described in 1), (n + m + k) is 1.0 or more and 22.0 or less, and n is 1.0 or more and 22.0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and each structural unit whose average number of structural units is represented by n, m, and k may be in any arrangement order. ]
- N + m + k is 22.0 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, More preferably, it is 4.0 or less, More preferably, it is 3.0 or less, From the same viewpoint, it is 1.0 or more, Preferably it is 1.5 or more, More preferably, it is 1.8 or more.
- n is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, further preferably, from the viewpoint of improving the dispersibility and storage stability of the dispersion. Is 5.0 or less, more preferably 4.0 or less, more preferably 3.0 or less.
- the ratio of n to (n + m + k) (n / (n + m + k)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the dispersant of the invention, it is 1.0 or less, preferably 0.9 or less.
- the average number of structural units, n, m, k, (n + m + k) can be measured, for example, by the method described in the examples.
- Each structural unit whose average number of structural units is represented by n, m, k may be in any arrangement order. When one or more of n, m, and k are plural, each structural unit may be in any arrangement order such as random or block.
- a dispersant made of the above compound is preferred.
- R x1 , R x2 , a, R 1 , R 2 , R 4 , R 5 , R 6 , (M 1 ) ⁇ , n and m are the same as those described in formula (1-1) (N + m) is 1.0 or more and 22.0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and each structural unit whose average number of structural units is represented by n and m may be in any arrangement order.
- the ratio of n to (n + m) (n / (n + m)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the dispersant of the invention, it is 1.0 or less.
- m in the formula (1-1) is preferably used from the viewpoint of obtaining a dispersion having a small average particle size, a low viscosity, and excellent storage stability.
- a dispersant composed of a compound represented by formula (1-1b) is more preferable.
- R x1 , R x2 , a, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ , n and k are the same as those described in formula (1-1)
- the (n + k) is 1.0 or more and 22.0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and each structural unit in which the average number of structural units is represented by n and k may be in any arrangement order. ]
- the ratio of n to (n + k) (n / (n + k)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the dispersant of the invention, it is 1.0 or less.
- R 3 is preferably an ethyl group or a methyl group, more preferably a methyl group.
- the dispersant of the present invention may be a mixture containing a compound represented by the formula (1′-1).
- a compound represented by the formula (1′-1) wherein R x1 , R x2 , a, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ and (M 2 ) ⁇ have been described in formula (1)
- Ni, mi and ki are the same as those described in the formula (1 ′), and (ni + mi + ki) is an integer of 1 to 22.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and each structural unit whose number of structural units is indicated by ni, mi, ki may be in any arrangement order.
- each structural unit whose number of structural units is indicated by ni, mi, ki may be in any arrangement order.
- (Ni + mi + ki) is 22 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11 or less, more preferably 7 or less, still more preferably 5 or less, still more preferably 4 or less, and even more. Preferably it is 3 or less, and from the same viewpoint, it is 1 or more, preferably 2 or more.
- the ratio of ni to (ni + mi + ki) (ni / (ni + mi + ki)) is preferably 0.3 or more, more preferably 0.6, from the viewpoint of dispersibility and storage stability of the dispersion containing the compound of the present invention. From the viewpoint of ease of production of the compound of the present invention, it is 1.0 or less, preferably 0.9 or less.
- Each structural unit in which the number of structural units is indicated by ni, mi, ki may be in any arrangement order. When one or more of ni, mi, and ki are plural, each structural unit may be in any arrangement order such as random or block.
- a compound in which ki in the formula (1′-1) is preferably 0, more specifically, represented by the formula (1′-1a) are preferred.
- R x1 , R x2 , a, R 1 , R 2 , R 4 , R 5 , R 6 and (M 1 ) ⁇ are the same as those described in formula (1); Is the same as that described in the formula (1 ′), and (ni + mi) is an integer of 1 to 22.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and each structural unit whose number is represented by ni and mi may be in any arrangement order.
- the ratio of ni to (ni + mi) (ni / (ni + mi)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the compound of the invention, it is 1.0 or less.
- the formula (1′-1) is preferable.
- a compound in which mi is 0, more specifically a compound represented by the formula (1′-1b) is preferable.
- R x1 , R x2 , a, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ , and (M 2 ) ⁇ are described in formula (1)
- Ni and ki are the same as those described in the formula (1 ′), and (ni + ki) is 1.0 or more and 22.0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and each structural unit whose number of structural units is indicated by ni and ki may be in any arrangement order. ]
- the ratio of ni to (ni + ki) (ni / (ni + ki)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the compound of the invention, it is 1.0 or less.
- the dispersant according to the second embodiment of the present invention is a dispersant comprising a compound having a p of 0.3 or more and 11.0 or less in the formula (1), and more specifically, preferably the formula (1 -2).
- R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ and (M 2 ) ⁇ , n, m, k, (n + p + m + k), and (n + p) are the same as those described in the formula (1), and p is 0.3 to 11.0.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average structure thereof is represented by n, p, m, or k. Each structural unit in which the number of units is shown may be in any arrangement order. ]
- p is 0.3 or more, preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.8 or more, From the same viewpoint, it is preferably 11.0 or less, preferably 5.5 or less, more preferably 3.5 or less, still more preferably 2.5 or less, still more preferably 2.0 or less, still more preferably 1. It is 5 or less, more preferably 1.0 or less, and still more preferably 0.8 or less.
- n / p is preferably 0.1 or more, more preferably 0.2 or more, and further preferably 0.3 or more, from the viewpoint of obtaining excellent developability.
- a dispersant comprising a compound of the formula (1) wherein p is 0.3 or more and 11.0 or less and k is 0. More specifically, a dispersant composed of the compound represented by the formula (1-2a) is preferable.
- R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 4 , R 5 , R 6 , (M 1 ) ⁇ , n, p, and m are It is the same as that described in (1-2), and (n + p + m) is 1.0 or more and 22.0 or less.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average number of structural units in n, p and m
- Each structural unit represented by may have any arrangement order.
- (N + p + m) is 22.0 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11.0 or less, more preferably 7.0 or less, and even more preferably 5.0 or less. More preferably, it is 4.0 or less, More preferably, it is 3.0 or less, From the same viewpoint, it is 1.0 or more, Preferably it is 1.5 or more, More preferably, it is 1.8 or more.
- the ratio of (n + p) to (n + p + m) [(n + p) / (n + p + m)] is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion.
- the average number of structural units, n, p, m, and (n + p + m) can be measured, for example, by the method described in the examples.
- Each structural unit whose average number of structural units is represented by n, p, and m may be in any arrangement order. When one or more of n, p, and m are plural, each structural unit may be in any arrangement order such as random or block.
- the dispersant of the present invention is preferably a dispersant comprising a compound having a pi of 1 or more and 11 or less in the formula (1 ′), more specifically, a compound represented by the formula (1′-2) It may be a mixture containing [Wherein, R x1 , R x2 , R y1 , R y2 , a, d, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ and (M 2 ) ⁇ are , Mi, mi, and ki are the same as those described in equation (1 ′), (ni + pi + mi + ki) is an integer of 2 to 22, and pi Is an integer from 1 to 11.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the structural unit is represented by ni, pi, mi, ki. Each structural unit whose number is shown may be in any arrangement order. ]
- (Ni + pi + mi + ki) is 22 or less from the viewpoint of improving the dispersibility and storage stability of the dispersion, preferably 11 or less, more preferably 7 or less, still more preferably 5 or less, still more preferably 4 or less, and even more. Preferably it is 3 or less, and 2 or more from the same viewpoint.
- Pi is 1 or more from the viewpoint of improving the dispersibility and storage stability of the dispersion, and is 11 or less from the same viewpoint, preferably 5 or less, more preferably 3 or less, and still more preferably 2 or less. Yes, more preferably 1.
- the ratio ((ni + pi) / (ni + pi + mi + ki)) between (ni + pi) and (ni + pi + mi + ki) is preferably in the same range as the preferred range of the formula (1 ′).
- the dispersant is preferably composed of a compound having a ki of 0 in the formula (1′-2).
- the compound represented by '-2a) is preferred.
- R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 4 , R 5 , R 6 and (M 1 ) ⁇ are those described in formula (1)
- Ni, pi, and mi are the same as those described in the formula (1′-2), and (ni + pi + mi) is an integer of 2 to 22.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the number of structural units is ni, pi, or mi. Each structural unit shown may be in any arrangement order.
- a preferred range of ni, pi, and mi in the formula (1′-2a) is the same as the above range.
- the ratio of (ni + pi) to (ni + pi + mi) ((ni + pi) / (ni + pi + mi)) is preferably 0.3 or more, more preferably 0.6 or more, from the viewpoint of improving the dispersibility and storage stability of the dispersion. From the viewpoint of ease of production of the compound of the present invention, it is 1.0 or less.
- the dispersant according to the third embodiment of the present invention includes a dispersant composed of a compound represented by the formula (1-1) and a compound represented by the following formula (1-3) It is a mixture with the dispersing agent which consists of.
- R y1 , R y2 , d, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ and (M 2 ) ⁇ are the same as those described in formula (1).
- P, m, and k represent the average number of structural units, (p + m + k) is from 1.0 to 22.0, m is from 0 to 21.0, and p is 1.
- the dispersant composed of the compound represented by the formula (1-1) in the mixture is preferably a dispersant composed of the compound represented by the formula (1-1a).
- the mass ratio of the dispersant composed of the compound represented by formula (1-1) to the dispersant composed of the compound represented by formula (1-3) in the mixture [(1-1) / (1-3 )] Is preferably 10/90 or more, more preferably 20/80 or more, still more preferably 30/70 or more, and still more preferably, from the viewpoint of excellent dispersibility, excellent storage stability, and excellent heat resistance. It is 40/60 or more, more preferably 45/55 or more, and preferably 90/10 or less, more preferably 80/20 or less, and further preferably 70/30 or less.
- the dispersant of the present invention is, for example, Step 1: Formula (B) in the molecular structure: [Wherein, R 4 and R 5 are the same as those described in formula (A). And a polyamine compound having an average number of structural units B contained in one molecular structure of 1.0 or more and 22.0 or less, Formula (3-1): [Wherein, R x1 , R x2 , a, and R 6 are the same as those described in the formula (A). Y 1 represents a group that becomes an anion (M 1 ) ⁇ by elimination.
- Y 1 is preferably a group that becomes the above-mentioned suitable (M 1 ) ⁇ by leaving.
- Y 1 is preferably a halogen atom, more preferably at least one selected from a chlorine atom, a bromine atom and an iodine atom, from the viewpoint of improving the ease of production of the dispersant and the dispersibility and storage stability of the dispersion. More preferably, it is a chlorine atom.
- R 4 , R 5 , R x1 , R x2 , a, R y1 , R y2 , d, and R 6 are the same as the above-described ranges.
- the dispersant of the present invention can be obtained by reacting the raw materials in the absence of a solvent or in a solvent.
- the solvent used in the reaction is preferably, for example, an ether organic solvent used in the present invention described later.
- the ether organic solvent is preferably (poly) alkylene glycol monoalkyl ether acetate, more preferably propylene glycol monomethyl ether acetate (hereinafter also referred to as “PGMEA”), diethylene glycol monobutyl ether acetate (hereinafter also referred to as “BCA”), photo From the viewpoint of easy handling and workability of the pigment dispersion in the lithography method, PGMEA is more preferable.
- the polyamine compound is, for example, the formula (2): [Wherein, R 1 , R 2 , R 4 , R 5 are the same as the substituents described in formula (A). (N + p + m + k) represents the average number of structural units and is 1.0 or more and 22.0 or less. ] The polyamine compound represented by this.
- the polyamine compound can be obtained, for example, by a method in which an alkylene diol and a primary amine or a secondary amine are reacted in the presence of a Cu—Ni catalyst, or a method in which an alkylene diamine is reductively alkylated with an aldehyde.
- a method in which an alkylene diamine is reductively alkylated with an aldehyde or a method in which an alkylene diamine is reductively alkylated with an aldehyde.
- N, N, N ′, N′-tetramethylhexanediamine (“Kaorizer No. 1” manufactured by Kao Corporation)
- Kao N, N, N ′, N′-tetramethylpropanediamine (Kao) “Kaorraiser No. 2” manufactured by Co., Ltd.)
- polyamine glycol (“Kaorraiser P200” manufactured by Kao Corporation) and the like can be used.
- the compound represented by the formula (3-1) forms [(C ⁇ O) R x1 O] in an alcohol having a hydrocarbon group of R x2 in the presence of a metal catalyst such as a titanium compound. It can be obtained by addition polymerization of a lactone to obtain an alkyloxypolyester, followed by dehydration condensation with a carboxylic acid having an alkyl halide.
- alkyloxy represents R x2 O— (R x2 represents the aforementioned hydrocarbon group).
- the halogenated alkyl ester represented by the formula (3-2) is obtained by, for example, reacting an alcohol having a hydrocarbon group of R y2 with an alkylene oxide compound that forms R y1 O in the presence of a basic substance.
- an alkoxypolyalkylene glycol followed by dehydration condensation with a carboxylic acid having an alkyl halide.
- alkoxy represents R y2 O— (R y2 represents the above-described hydrocarbon group).
- step 1 the ratio of the number of amine functional groups of the polyamine compound (for example, (n + p + m + k) in formula (2)) ⁇ molar amount to the compound (molar amount) represented by formula (3-1) is the target compound although it can be appropriately set according to, for example, 0.3 to 1.2.
- the ratio of the compound (molar amount) represented by the formula (3-2) to the number of amine functional groups of the polyamine compound (for example, (n + p + m + k) in the formula (2)) ⁇ molar amount in Step 1 is the target compound although it can be appropriately set according to, for example, 0.3 to 1.2.
- the reaction amount ratio between the polyamine compound and the halogenated alkyl ester compound is calculated from the number of amine functional groups of the polyamine compound and the halogen amount of the halogenated alkyl ester compound from the viewpoint of more accurately controlling the numbers of n and m. It is preferable to adjust based on the molar equivalent.
- the reaction atmosphere in this step is preferably a nitrogen gas atmosphere or an inert gas atmosphere such as argon.
- the reaction temperature in this step is, for example, preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and preferably 100 ° C. or lower.
- Step 2 The compound obtained in Step 1 and the formula (4): R 3 -Y 2 (4) [Wherein R 3 represents at least one selected from a hydrogen atom and a hydrocarbon group having 1 to 10 carbon atoms in which a part of the hydrogen atoms may be substituted with a hydroxyl group, and Y 2 is eliminated. This represents a group that becomes an anion (M 2 ) ⁇ . And a compound represented by the formula:
- R 3 is preferably the same as R 3 described above.
- a preferable example of Y 2 is a group which becomes the above preferable (M 2 ) ⁇ by elimination.
- Examples of the compound represented by the formula (4) include an acid and a quaternizing agent excluding the compound represented by the formula (3).
- Examples of the acid include hydrochloric acid, acetic acid, p-toluenesulfonic acid, and methylsulfuric acid.
- Examples of the quaternizing agent include dialkyl sulfate, alkyl halide, and alkyl p-toluenesulfonate.
- Examples of the dialkyl sulfate include dimethyl sulfate and diethyl sulfate.
- Examples of the alkyl halide include methyl chloride, methyl iodide, and benzyl chloride.
- Examples of the p-toluenesulfonate include methyl p-toluenesulfonate, p. -Ethyl toluenesulfonate and the like.
- the compound represented by the formula (4) is preferably at least one selected from hydrochloric acid, acetic acid, methyl chloride, dimethyl sulfate, and diethyl sulfate, more preferably at least one selected from acetic acid and dimethyl sulfate.
- the reaction atmosphere in this step is preferably a nitrogen gas atmosphere or an inert gas atmosphere such as argon.
- the temperature of the reaction in the step depends on the type of the compound represented by the formula (4), it is preferably 20 ° C. or higher from the viewpoint of reactivity, and from the viewpoint of suppressing coloring of the reaction product, etc. Preferably it is 100 degrees C or less.
- the pigment dispersion for a color filter of the present invention contains the dispersant of the present invention, an organic pigment, and an organic solvent.
- the organic pigment used in the present invention (hereinafter also simply referred to as “pigment”) is preferably used for color filters, and examples thereof include azo pigments, phthalocyanine pigments, condensed polycyclic pigments, lake pigments, and the like.
- azo pigment C.I. I. Insoluble azo pigments such as CI Pigment Red 3; I. Soluble red azo pigments such as CI Pigment Red 48: 1; I. And condensed azo pigments such as CI Pigment Red 144.
- the phthalocyanine pigment include C.I. I. A copper phthalocyanine pigment such as CI Pigment Blue 15: 6; I.
- CI Pigment Green 58 zinc phthalocyanine pigments such as CI Pigment Green 58.
- the condensed polycyclic pigment include C.I. I. Anthraquinone pigments such as CI Pigment Red 177; I. Perylene pigments such as CI Pigment Red 123; I. Perinone pigments such as C.I. Pigment Orange 43; I. Quinacridone pigments such as C.I. Pigment Red 122; I. Dioxazine pigments such as CI Pigment Violet 23, C.I. I. Pigment Yellow 109 and other isoindolinone pigments, C.I. I. Pigment Orange 66 and other isoindoline pigments, C.I. I.
- Quinophthalone pigments such as CI Pigment Yellow 138; I. Pigment azo complex pigments such as CI Pigment Yellow 150, C.I. I. Indigo pigments such as CI Pigment Red 88; I. Metal complex pigments such as C.I. Pigment Green 8; I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. And diketopyrrolopyrrole pigments such as CI Pigment Orange 71.
- a diketopyrrolopyrrole pigment represented by the formula (P1) (hereinafter also referred to as “DPP pigment”) is preferable from the viewpoint of more effectively expressing the effects of the present invention.
- X 11 and X 12 each independently represent a hydrogen atom, a halogen atom, or an aromatic hydrocarbon group in which a hydrogen atom may be substituted, and Y 11 and Y 12 are each Independently, it represents a hydrogen atom, —SO 3 H, or —SO 3 ⁇ Z + , and Z + represents a cation.
- X 11 and X 12 are preferably at least one selected from a halogen atom, more preferably a chlorine atom and a bromine atom.
- Y 11 and Y 12 are preferably a hydrogen atom.
- Y 11 and Y 12 are hydrogen atoms, and X 11 and X 12 are chlorine atoms (C Pigment Red 254: hereinafter also referred to as “PR254”) or a bromine atom.
- DPP pigments Commercially available products of DPP pigments include “S 3610 CF” (formerly “B-CF”), “S 3612 CF” (formerly “BK-CF”) of the product name “Irgaphor Red” series manufactured by BASF Japan Ltd., “S 3611 CF” (formerly “BT-CF”), “S 3621 CF”; “Ir gazein DPP Red” series “L 3660 HD” (former “BO”), “BL”; “Chromophthal DPP Red” series “BP”, “BOC”; “HOSTAPERM RED D2B” series “COF01”, “COFLV3781” manufactured by Clariant Inc .; “Chromofine Red 6156EC” manufactured by Dainichi Seika Kogyo Co.
- an organic pigment having an average primary particle diameter of preferably 100 nm or less, more preferably 20 to 60 nm.
- the average primary particle diameter of the organic pigment can be determined by a method of directly measuring the size of primary particles from an electron micrograph. Specifically, the diameter perpendicular to the major axis diameter of each primary particle is defined as the minor axis diameter, the minor axis diameter and the major axis diameter are measured, and the average value thereof is defined as the particle diameter of the particles.
- the volume average particle diameter is obtained by approximating the volume of each particle to a cube having the particle diameter as one side, and is defined as the average primary particle diameter.
- Said organic pigment can be used individually or in combination of 2 or more types.
- the content of the DPP pigment in the organic pigment of the present invention is preferably 20% by mass or more, more preferably 30% by mass or more, and further preferably 50% by mass with respect to the total amount of the pigment from the viewpoint of optimizing the color characteristics. % Or more, still more preferably 60% by mass or more, preferably 100% by mass or less, more preferably 90% by mass or less.
- the pigment dispersion of the present invention contains an organic solvent.
- the organic solvent is preferably an ether-based organic solvent from the viewpoint of enhancing the dispersibility of the pigment and the compatibility with the binder component used in the color filter, and achieving both substrate adhesion and developability of the resulting cured film. It is.
- the viscosity (unit: mPa ⁇ s) of the organic solvent at 25 ° C. is preferably 0.8 or more, more preferably 0.9 or more, and still more preferably from the viewpoint of easy handling of the pigment dispersion and the colored composition.
- the SP value (unit: (cal / cm 3 ) 1/2 ) of the organic solvent is obtained by increasing the compatibility with the binder component used for the color filter, moderate affinity with the pigment surface, low surface tension, and the like. From the viewpoint of improving the contrast of the cured film, it is preferably 7.5 or more, more preferably 8.0 or more, still more preferably 8.5 or more, preferably 10.5 or less, more preferably 9.5 or less, More preferably, it is 9.0 or less.
- the SP value is determined by the method of Fedors [Robert F.
- the boiling point of the organic solvent is preferably 50 ° C. or higher, more preferably 100 ° C. or higher, and still more preferably 120 ° C. or higher, from the viewpoint of work safety. Is 300 ° C. or lower, more preferably 260 ° C. or lower, and still more preferably 200 ° C. or lower.
- the organic solvent is preferably (poly) alkylene glycol monoalkyl ether acetate, (poly) alkylene glycol monoalkyl ether propionate and (poly) alkylene glycol dialkyl ether, more preferably (poly) from the viewpoint of enhancing the dispersion characteristics.
- Alkylene glycol monoalkyl ether acetate In this specification, “(poly) alkylene glycol” means at least one selected from alkylene glycol and polyalkylene glycol.
- Examples of (poly) alkylene glycol monoalkyl ether acetate include ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, PGMEA, propylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl Examples include ether acetate and BCA.
- PGMEA oiling point: 146 ° C., viscosity at 25 ° C .: 1.1 mPa ⁇ s, SP value: 8.73
- BCA oiling point: 247 ° C., at 25 ° C.
- the pigment dispersion for a color filter of the present invention preferably further contains an alkali-soluble resin.
- the alkali-soluble resin is usually used for dissolving a non-exposed portion in a developer when a color filter is produced by a photolithography method.
- Examples of the alkali-soluble resin include those generally used in negative resists, and those that are soluble in an alkaline aqueous solution, that is, dissolved in an aqueous 0.05 mass% tetramethylammonium hydroxide solution at 20 ° C. at 1 mass% or more. Anything to do.
- the alkali-soluble resin is preferably a copolymer including a structural unit (as1) derived from (meth) acrylic acid ester and a structural unit (as2) derived from a monomer having an acid group.
- the alkali-soluble resin may further contain a structural unit (as3) derived from another copolymerizable monomer.
- (meth) acrylic acid esters examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) ) Acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, n -Decyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, phenoxyethyl (meth) acrylate, cyclohexyl (meth) acrylate, isoborny
- Examples of the monomer having an acid group include at least one selected from (meth) acrylic acid, a dimer of acrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, and anhydrides thereof. It is done.
- Examples of other copolymerizable monomers include ether dimer of ⁇ -hydroxymethylacrylic acid, vinyl acetic acid, 2,2′-oxybis (methylene) bis-2-propenoate, styrene, ⁇ -methylstyrene. , Bifunctional acrylate, N-vinyl-2-pyrrolidone, N-methylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and N-phenylmaleimide.
- “(meth) acrylate” means at least one selected from acrylate and methacrylate
- “(meth) acrylic acid” means at least one selected from acrylic acid and methacrylic acid. .
- the alkali-soluble resin used in the present invention from the viewpoint of maintaining the dispersion of the pigment in the cured film and improving the contrast, preferably the structural unit derived from (meth) acrylic acid ester and (meth) acrylic acid-derived It is a copolymer containing a structural unit.
- the copolymer is preferably a copolymer containing a structural unit derived from benzyl (meth) acrylate and a structural unit derived from (meth) acrylic acid, and a structural unit derived from methyl (meth) acrylate and (meth) acrylic acid.
- copolymer containing at least one selected from a copolymer containing a structural unit derived from, more preferably a structural unit derived from benzyl (meth) acrylate and a structural unit derived from (meth) acrylic acid.
- alkali-soluble resin a resin in which a reactive group is further introduced into the above copolymer is also preferable from the viewpoint of reacting with a polyfunctional monomer described later at the time of exposure and improving developability.
- the reactive group is more preferably at least one selected from a glycidyl group and an ethylenically unsaturated group from the viewpoint of ease of production.
- Examples of such commercially available alkali-soluble resins include “RD-KA-501”, “RD-KA-502”, “BX-KA-01” of “ACRYCURE AXD” series manufactured by Nippon Shokubai Co., Ltd. “BX-KA-02”; “Aronix” series “M6100”, “M7100”, “M8030” manufactured by Toagosei Co., Ltd. may be mentioned.
- the amount of the structural unit (as1) derived from the acrylate ester is preferably 30% by mass or more, more preferably 50% by mass or more, still more preferably 60% by mass or more, and preferably 90% by mass or less. More preferably, it is 80 mass% or less, More preferably, it is 70 mass% or less.
- the amount of the structural unit (as2) derived from the monomer having an acid group is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 20% by mass or more, preferably It is 50 mass% or less, More preferably, it is 40 mass% or less, More preferably, it is 30 mass% or less.
- the amount of the constituent unit derived from other copolymerizable monomer (as3) is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 20% by mass or more. Preferably it is 50 mass% or less, More preferably, it is 40 mass% or less, More preferably, it is 30 mass% or less.
- the molar ratio [(as1) / (as2)] between the structural unit (as1) and the structural unit (as2) is preferably 90/10 to 50/50, more preferably 80/20 to 60/40.
- the weight average molecular weight of the alkali-soluble resin is preferably 5,000 or more, more preferably 10,000 or more from the viewpoint of the curability of the coating film, and preferably 50,000 or less, more preferably from the viewpoint of developability. Is 40,000 or less, more preferably 20,000 or less.
- the acid value (unit: mgKOH / g) of the alkali-soluble resin is preferably 50 or more, more preferably 80 or more from the viewpoint of dispersibility and developability, and preferably 260 or less from the viewpoint of the curability of the coating film. More preferably, it is 240 or less, More preferably, it is 220 or less.
- the dispersion of the present invention preferably contains an aromatic compound having two or more maleimide groups (hereinafter also referred to as “maleimide compound”) from the viewpoint of heat resistance.
- the maleimide compound is used to improve the heat resistance of the cured film by preventing the pigment from sublimation when the colored composition is cured and then exposed to high temperature conditions.
- the maleimide compound used in the present invention has at least one aromatic ring.
- maleimide compounds examples include 1,3-phenylene dimaleimide, 1,4-phenylene dimaleimide, 4-methyl-1,3-phenylene bismaleimide, 4,4′-diphenylsulfone bismaleimide, bis- (3-ethyl- And at least one selected from 5-methyl-4-maleimidophenyl) methane and 2,2-bis- [4- (4-maleimidophenoxy) phenyl] propane.
- the maleimide compound is preferably phenylene dimaleimide, more preferably N, N′-1,3-phenylene dimaleimide (hereinafter, referred to as “maleimide compound”) from the viewpoint of solubility in a solvent and improvement of heat resistance and substrate adhesion. , Also referred to as “PDM”).
- the method for producing a pigment dispersion of the present invention preferably includes the following steps from the viewpoint of producing a pigment dispersion for a color filter having a small average particle size, low viscosity, and excellent storage stability.
- a high-speed stirring and mixing apparatus such as a homomixer, a kneader such as a roll mill, a kneader, or an extruder, a high-pressure disperser such as a high-pressure homogenizer, a media-type disperser such as a paint shaker or a bead mill can be used.
- a high-speed stirring and mixing device such as a homomixer, and a media type dispersing machine such as a paint shaker or a bead mill are preferable.
- the material of the media used in the dispersion step is preferably a ceramic material such as zirconia or titania, a polymer material such as polyethylene or nylon, a metal, or the like, and zirconia is preferred from the viewpoint of wear.
- the diameter of the media is preferably 0.003 mm or more, more preferably 0.01 mm or more, preferably 0.5 mm or less, more preferably 0.4 mm or less, from the viewpoint of crushing the aggregated particles in the organic pigment. It is.
- the dispersion time is preferably 0.3 hours or more, more preferably 1 hour or more from the viewpoint of sufficiently miniaturizing the organic pigment, and preferably 200 hours or less, more preferably from the viewpoint of the production efficiency of the pigment dispersion. Is less than 50 hours.
- the dispersion method in the dispersion step of the present production method may obtain the desired pigment dispersion by dispersing the mixture once. However, after the mixture is pre-dispersed using a medium, the pre-dispersion step is further performed. It is preferable to perform this dispersion using a smaller medium from the viewpoint of obtaining a finer and more uniform pigment dispersion.
- the above-mentioned various dispersing machines can be used as the mixing and dispersing machine used for the preliminary dispersion.
- a media type dispersing machine such as a paint shaker or a bead mill is preferable.
- the diameter of the media used in the preliminary dispersion step is preferably 0.1 mm or more, preferably 0.5 mm or less, more preferably 0.4 mm or less, from the viewpoint of crushing the aggregated particles in the organic pigment. .
- the dispersion time in the preliminary dispersion step is preferably 0.1 hour or more, more preferably 0.5 hour or more, further preferably 1 hour or more from the viewpoint of crushing the aggregated particles in the organic pigment. From the viewpoint of production efficiency, it is preferably 10 hours or less, more preferably 5 hours or less, and even more preferably 4 hours or less.
- This dispersion is a step of dispersing the preliminary dispersion obtained in the preliminary dispersion, and is performed to further refine the mixture obtained in the preliminary dispersion step. From the viewpoint of miniaturizing the organic pigment, It is preferable to use a media-type disperser, and the above-described high-pressure disperser may be used in combination.
- the diameter of the media used in this dispersion step is preferably less than 0.1 mm, more preferably 0.08 mm or less, and even more preferably 0.07 mm or less from the viewpoint of miniaturizing the organic pigment, and the media is separated from the pigment. From this viewpoint, it is preferably 0.003 mm or more, and more preferably 0.01 mm or more.
- the dispersion time of this dispersion is preferably 2 hours or more, more preferably 3 hours or more from the viewpoint of sufficiently miniaturizing the organic pigment, and preferably 200 hours or less, from the viewpoint of the production efficiency of the pigment dispersion. Preferably it is 50 hours or less.
- the content of the organic pigment in the pigment dispersion of the present invention is preferably 3% by mass or more, more preferably 5% by mass or more, and still more preferably 10% by mass or more from the viewpoint of obtaining good colorability. From the viewpoint of reducing the average particle size in the dispersion and obtaining a pigment dispersion having a low viscosity, it is preferably 30% by mass or less, more preferably 20% by mass or less, and still more preferably 16% by mass or less.
- the mass ratio of the dispersant to the pigment in the pigment dispersion of the present invention [dispersant / pigment] is preferably 0.1 or more, more preferably from the viewpoint of improving the storage stability of the pigment dispersion and improving the contrast.
- Is 0.2 or more, more preferably 0.3 or more, from the viewpoint of increasing the blending amount of the binder component and from the viewpoint of improving the physical properties of the coating film preferably 1.5 or less, more preferably 1.2 or less, Preferably it is 0.9 or less, More preferably, it is 0.5 or less.
- the content of the organic solvent in the pigment dispersion of the present invention is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 60% by mass or more, from the viewpoint of reducing the viscosity of the dispersion. From the viewpoint of obtaining good colorability, it is preferably 95% by mass or less, more preferably 90% by mass or less.
- the content of the alkali-soluble resin in the pigment dispersion of the present invention is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 3% by mass or more, preferably 15% by mass or less, more preferably Is 12% by mass or less, more preferably 9% by mass or less.
- the content of the maleimide compound in the pigment dispersion of the present invention is preferably 0.2 parts by mass or more, more preferably 1 part by mass or more, still more preferably 3 parts by mass or more, with respect to 100 parts by mass of the pigment. Preferably it is 20 mass% or less, More preferably, it is 15 mass% or less, More preferably, it is 10 mass% or less.
- the average particle size in the pigment dispersion of the present invention is preferably 200 nm or less, more preferably 100 nm or less, still more preferably 90 nm or less, and even more preferably 70 nm or less in order to obtain a good contrast as a color material for a color filter. Yes, preferably 20 nm or more.
- the preferred range of the average particle size (hereinafter also referred to as “average particle size after storage”) when the pigment dispersion is stored under certain conditions, for example, at room temperature for one week, is the same as the aforementioned range.
- the average particle size and the average particle size after storage are measured by the method described in the examples.
- a pigment concentration of 10% by mass of the pigment dispersion of the present invention is preferably 2 or more, more preferably 3 or more, and still more preferably from the viewpoint of ease of production of the coating film. From the viewpoint of smoothness and optical properties of the coating film, it is preferably 200 or less, more preferably 50 or less, still more preferably 20 or less, and still more preferably 15 or less.
- a preferable range of the viscosity at 20 ° C. hereinafter also referred to as “viscosity after storage” when the pigment dispersion is stored under certain conditions, for example, at room temperature for one week is the same as the above-described range. The viscosity and the viscosity after storage are measured by the method described in the examples.
- the coloring composition for color filters of the present invention contains a pigment dispersion, a polyfunctional monomer, and a photopolymerization initiator.
- the coloring composition preferably further contains an alkali-soluble resin.
- Preferred alkali-soluble resins are the same as those described above.
- the content of the alkali-soluble resin in the coloring composition is preferably 10% by mass or more and 40% by mass or less in the effective component excluding the solvent of the coloring composition for color filter.
- the polyfunctional monomer preferably has a plurality of polymerizable groups, and more preferably has two or more ethylenically unsaturated double bonds.
- the polyfunctional monomer include (meth) acrylic acid ester, urethane (meth) acrylate, (meth) acrylic acid amide, allyl compound, vinyl ester and the like having two or more ethylenically unsaturated bonds.
- the polyfunctional monomer is preferably an acrylate ester having two or more ethylenically unsaturated double bonds, more preferably dipentaerythritol hexaacrylate (hereinafter also referred to as “DPHA”).
- the content of the polyfunctional monomer is preferably 5% by mass or more and 30% by mass or less in an effective amount excluding the solvent of the coloring composition for color filter.
- photopolymerization initiator examples include aromatic ketones, lophine dimers, benzoin, benzoin ethers, polyhalogens and the like.
- the photopolymerization initiator is preferably a combination of 4,4′-bis (diethylamino) benzophenone and 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 4- [pN, N— Di (ethoxycarbonylmethyl) -2,6-di (trichloromethyl) -s-triazine], 2-methyl-4 ′-(methylthio) -2-morpholinopropiophenone, 2- (4-methylbenzyl) -2 -(Dimethylamino) -1- (4-morpholinophenyl) butan-1-one (hereinafter also referred to as “MBz-MPB”), and 2- [4- (methylthio) benzoyl] -2- (4-morpholinyl) ) At least one
- binder components such as the alkali-soluble resin, polyfunctional monomer, photopolymerization initiator, polyfunctional oligomer, monofunctional monomer, and sensitizer can be used alone or in combination of two or more.
- the content of the binder component is preferably 20% by mass or more and 80% by mass or less in the effective component excluding the solvent of the color filter coloring composition.
- the colored composition of the present invention is used for producing a color filter.
- the colored composition of the present invention is applied on a substrate, photocured and developed to obtain a coating film (F-1), and the coating film obtained in the step (F-1). It is preferable to have a step (F-2) of obtaining a cured film by heating to 200 to 300 ° C.
- the coating in the step (F-1) is preferably performed on a glass substrate by a roll coater, slit coater, spray, bar coater, applicator, spin coater, dip coater, ink jet, or screen printing.
- the solvent is removed and left to stand horizontally from the viewpoint of obtaining a coating film having a uniform film thickness.
- the standing temperature is preferably 10 ° C. or higher, more preferably 15 ° C. or higher, from the viewpoint of solvent removal efficiency, and preferably from the viewpoint of suppressing the smoothness of the coating film, workability, polymerization of the polyfunctional monomer, and the like. Is 115 ° C. or lower, more preferably 95 ° C. or lower, still more preferably 35 ° C.
- the standing time depends on the standing temperature, but is preferably 10 minutes or longer, more preferably 30 minutes or longer, preferably 100 minutes or shorter, more preferably 60 minutes or shorter.
- the photocuring is preferably performed by irradiating the coating film with ultraviolet rays. Thereby, the polyfunctional monomer in the coloring composition undergoes a crosslinking reaction, and the coating film can be cured. Photocuring is preferably performed to leave a pattern on the glass substrate with subsequent development. Therefore, it is preferable that the photocuring is performed by placing a photomask in which a pattern is previously incorporated, and the portion of the coating film to be removed by development is not cured.
- the photocuring is preferably performed at an ultraviolet irradiation amount of 10 to 100 mJ / cm 2 .
- Development is preferably performed by immersing the cured coating film after photocuring in an alkaline aqueous solution, and preferably rinsing with water to remove uncured portions.
- the alkaline aqueous solution used preferably has an alkali agent concentration of 0.001 to 10% by mass, preferably 0.01 to 1% by mass.
- the alkaline agent used for development is preferably an aqueous solution of ammonia, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, triethanolamine, tetramethylammonium hydroxide, and more preferably an aqueous tetramethylammonium hydroxide solution.
- the pH of the alkaline aqueous solution is preferably 10.0 to 13.0.
- Step (F-2) is a step of obtaining a cured film by heating the coating film obtained in the step (F-1) to 200 to 300 ° C.
- Step (F-2) is a post-baking step, and by performing this step, a cured film with higher hardness can be formed.
- the heating temperature is preferably 210 to 280 ° C, more preferably 220 to 270 ° C.
- the heating time is preferably 5 to 120 minutes, more preferably 10 to 40 minutes.
- the present invention further discloses the following dispersant, a production method at the time of dispersion, a coloring composition for a color filter, a color filter, and a production method of the color filter with respect to the above-described embodiment.
- a dispersant having a structural unit A represented by the formula (A) in a molecular structure and an average number of structural units A contained in one molecular structure being 1.0 or more and 22.0 or less.
- R x1 represents an alkanediyl group having 2 to 12 carbon atoms
- R x2 represents a hydrocarbon group having 1 to 18 carbon atoms
- a represents an average addition mole number
- R 4 represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms
- R 6 represents an alkanediyl group having 1 to 4 carbon atoms
- (M 1 ) ⁇ represents an anion.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different.
- the average number of structural units A contained in the dispersant single molecular structure is 1.0 or more, preferably 1.5 or more, more preferably 1.8 or more, and 22.0 or less.
- the dispersant according to ⁇ 1> preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0 or less, and still more preferably 3.0 or less. .
- the carbon number of R x1 is 2 or more, preferably 3 or more, more preferably 4 or more, still more preferably 5 or more, 12 or less, preferably 10 or less, more preferably 7 or less, More preferably, it is 6 or less, More preferably, it is 5 or less,
- R x1 is preferably at least one selected from an ethylene group, various propanediyl groups, various butanediyl groups, various pentanediyl groups, various hexanediyl groups, and various heptanediyl groups, more preferably butane-1, ⁇ 1> to ⁇ 3>, which are at least one selected from 4-diyl, pentane-1,5-diyl and hexane-1,6-diyl, more preferably pentane-1,5-diyl.
- the dispersing agent in any one of.
- ⁇ 5> a is 2 or more, preferably 10 or more, more preferably 15 or more, 100 or less, preferably 70 or less, more preferably 50 or less, from ⁇ 1> to ⁇ 4> The dispersing agent in any one.
- the carbon number of R x2 is 1 or more, preferably 6 or more, more preferably 10 or more, 18 or less, preferably 16 or less, more preferably 14 or less, ⁇ 1> to The dispersant according to any one of ⁇ 5>.
- Rx2 is preferably at least one selected from an aliphatic hydrocarbon group and a hydrocarbon group having an aromatic ring, more preferably an aliphatic hydrocarbon group, still more preferably an alkyl group and an alkenyl group.
- R x2 is preferably methyl group, ethyl group, octyl group, decyl group, lauryl group, myristyl group, cetyl group, oleyl group, stearyl group, phenyl group, p-octylphenyl group, and p-nonylphenyl.
- At least one selected from a group more preferably at least one selected from a methyl group, an octyl group, a decyl group, a lauryl group, an oleyl group, and a stearyl group, more preferably a methyl group, an octyl group, a decyl group, and a lauryl group.
- R 4 The carbon number of R 4 is 10 or less, preferably 4 or less, more preferably 2 or less, and preferably 1 or more, and more preferably 1, ⁇ 1> to ⁇ 8 >
- the dispersing agent in any one of>.
- R 4 is preferably a hydrocarbon group not substituted with a hydroxyl group.
- R 4 is preferably at least one selected from a methyl group, an ethyl group, various propyl groups, and various butyl groups, more preferably at least one selected from a methyl group and an ethyl group, and even more preferably methyl.
- the dispersant according to any one of ⁇ 1> to ⁇ 10> which is a group.
- the carbon number of the alkanediyl group of R 5 is 1 or more, preferably 2 or more, more preferably 3 or more, 18 or less, preferably 14 or less, more preferably 10 or less, still more preferably.
- R 5 is preferably at least one selected from ethylene group, various propanediyl groups, various hexanediyl groups, and various nonanediyl groups, more preferably propane-1,3-diyl group, hexane-1,6 At least one selected from a -diyl group and a nonane-1,9-diyl group, more preferably at least one selected from a propane-1,3-diyl group and a hexane-1,6-diyl group, The dispersant according to any one of 1> to ⁇ 12>.
- the carbon number of R 6 is 4 or less, preferably 3 or less, more preferably 2 or less, and preferably 1 or more, and more preferably 1, ⁇ 1> to ⁇ 13 >
- R 6 is preferably a methylene group.
- (M 1 ) ⁇ is preferably at least one selected from a halide ion, an alkyl sulfate ion, an alkylbenzene sulfonate ion, and an alkyl carbonate ion, more preferably a halide ion, and still more preferably a chloride.
- the dispersant according to any one of ⁇ 1> to ⁇ 15> which is at least one selected from ions, bromide ions, and iodide ions, and more preferably a chloride ion.
- the dispersant preferably has at least one selected from the structural unit B represented by the formula (B) and the structural unit C represented by the formula (C) in one molecular structure.
- ⁇ 1> to ⁇ 16> are selected from the structural unit B represented by the formula (B) and the structural unit C represented by the formula (C) in one molecular structure.
- R 4 represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms. .
- R 3 represents at least one selected from a hydrogen atom and a hydrocarbon group having 1 to 10 carbon atoms in which part of the hydrogen atoms may be substituted with a hydroxyl group
- R 4 represents a hydrogen atom
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms
- (M 2 ) ⁇ represents an anion.
- R 3 is preferably at least one selected from a hydrogen atom and a hydrocarbon group having 1 to 10 carbon atoms.
- R 3 is preferably at least one selected from a hydrogen atom, a methyl group, an ethyl group, a propyl group, and a benzyl group, more preferably at least one selected from a hydrogen atom and a methyl group, ⁇ 17
- ⁇ 21> (M 2 ) ⁇ is preferably at least selected from carboxylate ions, sulfonate ions, halide ions, sulfate ions, nitrate ions, nitrite ions, phosphate ions, phosphite ions, and carbonate ions.
- ⁇ 22> (M 2 ) ⁇ is preferably at least one selected from a carboxylate ion, a halide ion, an alkylsulfate ion, and an alkylbenzenesulfonate ion, and any one of ⁇ 17> to ⁇ 21> The dispersant described.
- R 4 represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group
- R 5 represents an alkanediyl group having 1 to 18 carbon atoms
- R 6 represents an alkanediyl group having 1 to 4 carbon atoms
- (M 1 ) ⁇ represents an anion.
- [R y1 O] may be the same or different when there are a plurality of [R y1 O].
- the average number of structural units D contained in one molecular structure is preferably 0.3 or more, more preferably 0.5 or more, still more preferably 0.6 or more, and still more preferably.
- the dispersant preferably has an array structure including one or more structural units A, and more preferably, the structural unit A, optionally the structural unit B, the structural unit C, and the structural unit D are included in one molecular structure.
- a sequence structure containing at least one selected from the above and more preferably having a sequence structure containing at least one selected from the structural unit A, optionally the structural unit B, and the structural unit C in one molecular structure. More preferably, it has an array structure including at least one selected from the structural unit A and the structural unit D, optionally the structural unit B, and the structural unit C in a single molecular structure, ⁇ 1> to ⁇ 24>
- the dispersing agent in any one of. ⁇ 26>
- the total average number of structural units A, B, C and D in the molecular structure in the dispersant is preferably 22.0 or less, more preferably 11.0 or less, and still more preferably.
- a hydrocarbon group having 1 to 10 carbon atoms which has an array structure containing one or more of the structural units A, and the terminal of the array structure may preferably have a hydrogen atom partially substituted with a hydroxyl group.
- the dispersant is at least one selected from a hydrocarbon group having 1 to 10 carbon atoms and a hydroxyalkyl group having 2 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 5 carbon atoms and 3 or more carbon atoms. At least one selected from hydroxyalkyl groups having 6 or less, more preferably at least one selected from hydrocarbon groups having 1 to 3 carbon atoms and hydroxyalkyl groups having 4 to 6 carbon atoms,
- the dispersant according to any one of ⁇ 26>. ⁇ 28>
- the weight average molecular weight Mw of the dispersant is preferably 2,000 or more, more preferably 3,000 or more, still more preferably 3,500 or more, and preferably 50,000 or less, more preferably 25.
- the dispersant according to any one of ⁇ 1> to ⁇ 27> which is not more than 1,000, more preferably not more than 20,000, still more preferably not more than 15,000.
- R x1 represents an alkanediyl group having 2 to 12 carbon atoms
- R x2 represents a hydrocarbon group having 1 to 18 carbon atoms
- a represents an average addition mole number
- R y1 represents an alkanediyl group having 2 to 4 carbon atoms
- R y2 represents a hydrocarbon group having 1 to 18 carbon atoms
- d represents an average addition mole number, and is 1 to 100.
- R 1 , R 2 and R 4 may be the same or different, each represents a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms may be substituted with a hydroxyl group, and R 3 represents hydrogen And at least one selected from a hydrocarbon group having 1 to 10 carbon atoms in which a part of atoms and hydrogen atoms may be substituted with a hydroxyl group, and R 5 represents an alkanediyl group having 1 to 18 carbon atoms (provided that R 5 adjacent to R 1 represents a single bond R 6 represents an alkanediyl group having 1 to 4 carbon atoms, (M 1 ) ⁇ and (M 2 ) ⁇ each independently represents an anion, and n, p, m and k are average structures (N + p + m + k) is 1.0 or more and 22.0 or less, (n + p) is 1.0 or more and 22.0 or less, n is 0.3 or more and 22.0 or less, and p is
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average structure thereof is represented by n, p, m, or k. Each structural unit in which the number of units is shown may be in any arrangement order. ]
- n + p + m + k is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0 or less, and even more preferably 3.
- the compound according to ⁇ 29> which is 0.0 or less, 1.0 or more, preferably 1.5 or more, more preferably 1.8 or more.
- ⁇ 31> (n + p) is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0 or less, and even more preferably 3.
- the compound according to ⁇ 29> or ⁇ 30> which is 0.0 or less, 1.0 or more, preferably 1.5 or more, more preferably 1.8 or more.
- n is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0 or less, and even more preferably 3.0. Is 0.3 or more, preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.8 or more, still more preferably 1.0 or more, preferably 1.5 or more, more The compound according to any one of ⁇ 29> to ⁇ 31>, which is preferably 1.8 or more.
- ⁇ 33> p is 0 or more, preferably 0.3 or more, more preferably 0.5 or more, still more preferably 0.6 or more, still more preferably 0.8 or more, and preferably 11.
- ⁇ 29> to ⁇ 32> further preferably 0.8 or less.
- ⁇ 34> m is 21.0 or less, preferably 4.0 or less, more preferably 2.0 or less, still more preferably 1.0 or less, still more preferably 0.5 or less, and 0 or more.
- ⁇ 35> is 21.0 or less, preferably 4.0 or less, more preferably 2.0 or less, still more preferably 1.2 or less, and 0 or more, ⁇ 29> to ⁇ 34> The compound in any one of.
- the ratio of (n + p) to (n + p + m + k) ((n + p) / (n + p + m + k)) is preferably 0.3 or more, more preferably 0.6 or more, and 1.0 or less, preferably The compound according to any one of ⁇ 29> to ⁇ 35>, which is 0.9 or less.
- R 1 and R 2 have 10 or less carbon atoms, preferably 8 or less, more preferably 6 or less, and still more preferably 1. .
- R 1 and R 2 are preferably a hydrocarbon group not substituted with a hydroxyl group.
- R 1 and R 2 are preferably at least one selected from a hydrocarbon group having 1 to 10 carbon atoms and a hydroxyalkyl group having 2 to 6 carbon atoms, more preferably carbon atoms having 1 to 5 carbon atoms.
- At least one selected from a hydroxyalkyl group having 3 to 6 carbon atoms more preferably at least one selected from a hydrocarbon group having 1 to 3 carbon atoms and a hydroxyalkyl group having 4 to 6 carbon atoms.
- R 1 and R 2 are preferably at least one selected from a methyl group, an ethyl group, a butyl group, a hexyl group, a hydroxymethyl group, a hydroxybutyl group, and a hydroxyhexyl group, more preferably methyl.
- ⁇ 29> to ⁇ 40> which is at least one selected from a group, an ethyl group, a hydroxybutyl group, and a hydroxyhexyl group, more preferably at least one selected from a methyl group and a hydroxyhexyl group.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the average number of structural units in n, p and m
- Each structural unit represented by may have any arrangement order.
- n in the formula (1a) is 22.0 or less, preferably 11.0 or less, more preferably 7.0 or less, still more preferably 5.0 or less, still more preferably 4.0 or less, and further The compound according to ⁇ 42>, which is preferably 3.0 or less, 1.0 or more, preferably 1.5 or more, more preferably 1.8 or more.
- ⁇ 44> m in the formula (1a) is 21.0 or less, preferably 4.0 or less, more preferably 2.0 or less, still more preferably 1.0 or less, and still more preferably 0.5 or less.
- the ratio of (n + p) to (n + p + m) ((n + p) / (n + p + m)) is preferably 0.3 or more, more preferably 0.6 or more, and 1.0 or less, ⁇ 42
- R x1 , R x2 , a, R y1 , R y2 , d, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , (M 1 ) ⁇ and (M 2 ) ⁇ are , Ni, pi, mi and ki represent the number of structural units, (ni + pi + mi + ki) is an integer from 1 to 22, and ni is an integer from 1 to 22.
- pi is an integer from 0 to 11
- mi is an integer from 0 to 21
- ki is an integer from 0 to 21.
- a plurality of [(C ⁇ O) R x1 O] may be the same or different, and a plurality of [R y1 O] may be the same or different, and the structural unit is represented by ni, pi, mi, ki.
- Each structural unit whose number is shown may be in any arrangement order.
- ⁇ 47> (ni + pi + mi + ki) is 22 or less, preferably 11 or less, more preferably 7 or less, still more preferably 5 or less, still more preferably 4 or less, still more preferably 3 or less, and 1 or more.
- the compound according to ⁇ 46> preferably 2 or more.
- ⁇ 48> ni is 22 or less, preferably 11 or less, more preferably 7 or less, still more preferably 5 or less, still more preferably 4 or less, still more preferably 3 or less, and preferably 1 or more, preferably
- ⁇ 49> pi is 0 or more, preferably 1 or more, 11 or less, preferably 5 or less, more preferably 3 or less, still more preferably 2 or less, and even more preferably 1. 46.
- ⁇ 50> mi is 21 or less, preferably 4 or less, more preferably 2 or less, further preferably 1 or less, 0 or more, and even more preferably 0, ⁇ 46> to ⁇ 49>
- the compound in any one of. ⁇ 51> The compound according to any one of ⁇ 46> to ⁇ 50>, wherein ki is 21 or less, preferably 4 or less, more preferably 2 or less, still more preferably 1 or less, and 0 or more.
- the ratio of (ni + pi) to (ni + pi + mi + ki) ((ni + pi) / (ni + pi + mi + ki)) is preferably 0.3 or more, more preferably 0.6 or more, and 1.0 or less, preferably The compound according to any one of ⁇ 46> to ⁇ 51>, which is 0.9 or less.
- the ratio of (ni + pi) to (ni + pi + mi) ((ni + pi) / (ni + pi + mi)) is preferably 0.3 or more, more preferably 0.6 or more, and 1.0 or less, ⁇ 53 The compound as described in>.
- Step 1 Formula (B) in the molecular structure: [Wherein, R 4 and R 5 are the same as those described in formula (A). And a polyamine compound having an average number of structural units B contained in one molecular structure of 1.0 or more and 22.0 or less, Formula (3-1): [Wherein, R x1 , R x2 , a, and R 6 are the same as those described in the formula (A). Y 1 represents a group that becomes an anion (M 1 ) ⁇ by elimination. And a compound represented by Optionally, formula (3-2): [Wherein, R y1 , R y2 , d, and R 6 are the same as those described in the formula (D).
- Y 1 represents a group that becomes an anion (M 1 ) ⁇ by elimination.
- the polyamine compound is preferably the formula (2): [Wherein, R 1 , R 2 , R 4 , R 5 are the same as the substituents described in formula (A). (N + p + m + k) represents the average number of structural units and is 1.0 or more and 22.0 or less. ]
- the manufacturing method of the dispersing agent as described in ⁇ 55> which is a polyamine compound represented by these.
- Step 2 The compound obtained in Step 1 and the formula (4): R 3 -Y 2 (4) [Wherein R 3 represents at least one selected from a hydrogen atom and a hydrocarbon group having 1 to 10 carbon atoms in which a part of the hydrogen atoms may be substituted with a hydroxyl group, and Y 2 is eliminated. This represents a group that becomes an anion (M 2 ) ⁇ .
- the manufacturing method of the dispersing agent as described in ⁇ 55> or ⁇ 56> which has a process with which the compound represented by this is made to react.
- a pigment dispersion for a color filter comprising the dispersant according to any one of ⁇ 1> to ⁇ 28>, an organic pigment, and an organic solvent.
- a pigment dispersion for a color filter comprising a dispersant comprising the compound according to any one of ⁇ 29> to ⁇ 45>, an organic pigment, and an organic solvent.
- a pigment dispersion for a color filter comprising a dispersant containing the compound according to any one of ⁇ 46> to ⁇ 54>, an organic pigment, and an organic solvent.
- X 11 and X 12 each independently represent a hydrogen atom, a halogen atom, or an aromatic hydrocarbon group in which a hydrogen atom may be substituted; Y 11 and Y 12 are Each independently represents a hydrogen atom, —SO 3 H, or —SO 3 ⁇ Z + , where Z + represents a cation.
- X 11 and X 12 are preferably at least one selected from a halogen atom, more preferably a chlorine atom and a bromine atom.
- Y 11 and Y 12 are preferably a hydrogen atom.
- the content of the diketopyrrolopyrrole pigment in the organic pigment is preferably 20% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more, and still more based on the total amount of the pigment.
- the pigment dispersion for a color filter according to ⁇ 61> which is preferably 60% by mass or more, preferably 100% by mass or less, more preferably 90% by mass or less.
- the organic solvent is preferably at least one selected from propylene glycol monomethyl ether acetate and diethylene glycol monobutyl ether acetate, more preferably propylene glycol monomethyl ether acetate, according to any one of ⁇ 61> to ⁇ 63> Pigment dispersion for color filters.
- the alkali-soluble resin is preferably a copolymer including a structural unit (as1) derived from a (meth) acrylic acid ester and a structural unit (as2) derived from a monomer having an acid group, ⁇ 61
- the molar ratio [(as1) / (as2)] of the structural unit (as1) and the structural unit (as2) of the alkali-soluble resin is preferably 90/10 to 50/50, more preferably 80/20 to
- the content of the organic pigment in the pigment dispersion is preferably 3% by mass or more, more preferably 5% by mass or more, still more preferably 10% by mass or more, preferably 30% by mass or less, more preferably
- the mass ratio of the dispersant to the pigment in the pigment dispersion [dispersant / pigment] is preferably 0.1 or more, more preferably 0.2 or more, still more preferably 0.3 or more, preferably
- the content of the organic solvent in the pigment dispersion is preferably 30% by mass or more, more preferably 50% by mass or more, still more preferably 60% by mass or more, preferably 95% by mass or less, more preferably.
- the pigment dispersion for color filters according to any one of ⁇ 61> to ⁇ 69> which is 90% by mass or less.
- the content of the alkali-soluble resin in the pigment dispersion is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 3% by mass or more, and preferably 15% by mass or less.
- the content of the maleimide compound in the pigment dispersion is preferably 0.2 parts by mass or more, more preferably 1 part by mass or more, further preferably 3 parts by mass or more, with respect to 100 parts by mass of the pigment.
- the pigment dispersion for a color filter according to ⁇ 68> preferably 20% by mass or less, more preferably 15% by mass or less, and still more preferably 10% by mass or less.
- the average particle size of the pigment dispersion is preferably 200 nm or less, more preferably 100 nm or less, still more preferably 90 nm or less, still more preferably 70 nm or less, and preferably 20 nm or more, ⁇ 58> to ⁇ 73 >
- the viscosity (unit: mPa ⁇ s) at 20 ° C. when the pigment concentration of the pigment dispersion is 10% by mass is preferably 2 or more, more preferably 3 or more, still more preferably 5 or more, and preferably 200 or less.
- a coloring composition for a color filter comprising the dispersion according to any one of ⁇ 58> to ⁇ 75>, a polyfunctional monomer, and a photopolymerization initiator.
- the color filter coloring composition according to ⁇ 76> wherein the content of the alkali-soluble resin is preferably 10% by mass or more and 40% by mass or less, in an effective amount excluding the solvent of the color filter coloring composition.
- the polyfunctional monomer is preferably an acrylate ester having two or more ethylenically unsaturated double bonds, more preferably dipentaerythritol hexaacrylate. Coloring composition.
- the content of the polyfunctional monomer is preferably 5% by mass or more and 30% by mass or less in an effective amount excluding the solvent of the coloring composition for a color filter, and any one of ⁇ 76> to ⁇ 78>
- the coloring composition for color filters as described.
- the content of the photopolymerization initiator is preferably 0.2% by mass or more and 20% by mass or less, in an effective amount excluding the solvent of the color filter coloring composition, ⁇ 76> to ⁇ 79>
- the coloring composition for color filters in any one.
- ⁇ 81> A color filter produced using the color filter coloring composition according to any one of ⁇ 76> to ⁇ 80>.
- a method for producing a color filter which comprises the step (F-2) of heating the coating film obtained in the step 200 to 300 ° C. to obtain a cured film.
- X in the notation “polyester (X)” means the average degree of polymerization of structural units constituting the polyester (hereinafter also referred to as “average degree of polymerization of polyester”), and “polyalkylene glycol”.
- Y in the notation “(Y)” means the average number of moles of alkylene oxide added to the polyalkylene glycol.
- Average polymerization degree (integral value of signal derived from methylene group adjacent to oxygen atom of ester group constituting alkyloxypolyester) / (derived from methylene group adjacent to oxygen atom of ester group derived from trifluoroacetic acid) Integral value of signal) + 1
- the weight average molecular weight was measured by either ⁇ Condition 1> or ⁇ Condition 2> below.
- the measurement sample was prepared by the following method. The amount in which the solid content of the solution containing the compound obtained in the below-mentioned production example becomes 0.01 g is taken in a glass bottle ("Screw tube No. 5" manufactured by Maruemu Co., Ltd.), and the following eluent is added to make a total volume of 10 mL. And sealed. Subsequently, the glass bottle was stirred at 2,500 r / min for 1 minute using a test tube mixer (“Minishaker MS1” manufactured by IKA), and 100 ⁇ L of the resulting solution was used as a measurement sample.
- Gel chromatography (GPC method, apparatus: “HLC-8320GPC” manufactured by Tosoh Corporation) was prepared by using a solution obtained by dissolving dimethyldodecylamine (“Farmin DM20” manufactured by Kao Corporation) at 1 mmol / L in chloroform. ”, Detector: differential refractometer attached to the apparatus, column:“ K-804L ” ⁇ 2, manufactured by Showa Denko KK, flow rate: 1.0 mL / min, column temperature: 40 ° C.). The following monodisperse polystyrene was used as a standard substance.
- HEC-8320GPC manufactured by Tosoh Corporation
- detector differential refractometer attached to the apparatus
- column “TSK-GEL ⁇ -M” ⁇ 2, manufactured by Tosoh Corporation, flow rate: 0.6 mL / min, column temperature : 40 ° C).
- the following monodispersed polyethylene glycol was used as a standard substance.
- Solid content (mass%) [(mass after drying g) ⁇ (Petri dish + glass rod + mass g of dry anhydrous sodium sulfate)] / (mass g of sample) ⁇ 100
- reaction rate Cl ratio standard of chlorine ion amount Since the chlorine of the alkyloxypolyester monochloroacetate is converted into a chlorine ion by the reaction, the reaction rate Cl based on the ratio of the chlorine ion amount was calculated from the following equation.
- Reaction rate Cl (%) [chlorine ion amount (mass%)] / [total chlorine content (mass%)] ⁇ 100
- the chlorine ion content was determined by the Volhard method, and the total chlorine content was determined by the Volhard method after decomposition with sodium butyrate.
- reaction rate Am amine value reduction rate standard
- reaction rate Am (%) [(amine value before reaction mgKOH / g) ⁇ (amine value after reaction mgKOH / g)] / (amine value before reaction mgKOH / g) ⁇ 100
- the amine value was measured by “tertiary amine value” of ASTM D2073-66.
- Measurement of average number of structural units (n + p + m + k), n, p, m, and k in formula (1) in the dispersant (n + p + m + k) in formula (1) is the average amine functionality of the polyamine compound before the reaction It is obtained from the radix ((n + p + m + k) in the formula (1)).
- the average number of amine functional groups is determined by the integral ratio of 1 H-NMR measurement of the polyamine compound. More specifically, in the case of having an OH group at the terminal as in Synthesis Examples c2 and c3, the 1 H-NMR measurement of the obtained polyamine compound was conducted according to the method described in “Confirmation of quaternization reaction”.
- the ratio of (n KOH + p KOH ), m KOH and k KOH, which will be described later, is the ratio of (n + p), m and k, and (n + p) + m + k is the polyamine compound used for the synthesis of the dispersant in the production example.
- (N + p), m, and k are calculated to be equal to the average number of amine functional groups (n + p + m + k).
- (N KOH + p KOH ) and k KOH are numerical values obtained by converting the number of quaternary ammonium groups contained in the structural unit represented by (n + p) and k into amine values.
- N KOH + p KOH is calculated from the following equation.
- the (M 1 ) ⁇ and (M 2 ) ⁇ amounts are measured by the following method.
- a 0.1 g solution containing the dispersant obtained in the production example described below was diluted 1,000 to 5,000 times with ultrapure water to obtain a solution having a known dispersant concentration, and 25 ⁇ L of the sample was measured.
- Samples were measured by ion chromatography (device: “Dionex ICS-2100” manufactured by Thermo Scientific, suppressor: “ASRS-300”, detector: electrical conductivity detector attached to the device, detector temperature: 35 ° C, column: “Ion Pac AS11-HC” + “Ion Pac AG11-HC” manufactured by Nippon Dionex Co., Ltd., flow rate: 1.5 mL / min, column temperature: 35 ° C., eluent: potassium hydroxide solution) .
- the eluent concentration is a linear gradient elution from 10 mmol / L to 40 mmol / L (25 min).
- a sodium salt of (M 1 ) ⁇ or (M 2 ) ⁇ is used.
- sodium methyl sulfate manufactured by Tokyo Chemical Industry Co., Ltd., reagent
- sodium ethyl sulfate manufactured by Tokyo Chemical Industry Co., Ltd., reagent
- the (M 1 ) ⁇ or (M 2 ) ⁇ amount (% by mass) in the compound is obtained.
- p and n are determined by the integral ratio of 1 H-NMR measurement of the dispersant.
- n KOH [n KOH + p KOH] ⁇ (s / a) / [(s / a) + ⁇ (t 1 ⁇ 2/3) / d1 + (t 2/2) / d2 ⁇ / 2]
- p KOH [n KOH + p KOH] [n KOH + p KOH ] ⁇ (
- ultraviolet fiber spot irradiation device (“HTE-505-HA-X” manufactured by Hitec Co., Ltd., lamp: “USH-500MB” manufactured by Ushio Lighting Co., Ltd.), ultraviolet rays are applied to the substrate through the photomask at 40 mJ / cm. 2 irradiated.
- the substrate after ultraviolet irradiation was immersed in an aqueous solution containing 0.35% by mass of sodium carbonate and 0.2% by mass of polyoxyethylene distyrenated phenyl ether (“Emulgen A-60” manufactured by Kao Corporation). did. After the exposure pattern began to appear, the substrate was further immersed for 20 seconds, and then the substrate was rinsed with ion-exchanged water to remove water remaining on the substrate.
- a thin line on the substrate developed by the photomask was observed using an optical microscope, and the line width of the thinnest thin line remaining on the substrate was used as an index of fine line adhesion. The smaller the line width, the better the fine line adhesion and the better the developability.
- the substrate was further heat-treated in a clean oven at 230 ° C. for 80 minutes, and the film thickness (T 100 ) of the coating film was measured.
- Synthesis Example a2 [Polyester a2: Synthesis of octyloxypoly ( ⁇ -caprolactone) (20)] Octyloxypoly ( ⁇ -caprolactone) (20) in the same manner as in Synthesis Example a1 except that the reaction vessel is a 1 L flask, the alcohol and lactone are listed in Table 1 below, and tetrabutyl orthotitanate is 0.0085 g. Polyester a2) was obtained.
- Synthesis Example b1 [Chloroacetate b1: Synthesis of lauryloxypoly ( ⁇ -caprolactone) (21) monochloroacetate]
- a 10 L flask equipped with a stirrer, thermometer, nitrogen blowing tube, and cooling tube 4,790 g of polyester a1 obtained in Synthesis Example 1, monochloroacetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) 199 g, p- 17.5 g of toluenesulfonic acid monohydrate (manufactured by Kishida Chemical Co., Ltd., special grade reagent) was charged and stirring was started. The flask was purged with nitrogen, reacted at 140 ° C.
- Synthesis Example b2 [Chloroacetate b2: Octyloxypoly ( ⁇ -caprolactone) (20) Synthesis of monochloroacetate]
- the reaction vessel was a 1 L flask, using the polyester and monochloroacetic acid listed in Table 2 below, except that p-toluenesulfonic acid monohydrate was 1.48 g and “Kyoward 500SH” was 16.8 g.
- octyloxypoly ( ⁇ -caprolactone) (20) monochloroacetate (chloroacetate b2) was obtained.
- Synthesis Examples b3 to b10 [Chloroacetate b3 to b10: Synthesis of alkoxypolylactone monochloroacetate] Alkoxypolylactone monochloroacetates b3 to b10 were obtained in the same manner as in Synthesis Example b2 except that the polyesters and monochloroacetic acid listed in Table 2 were used.
- Synthesis Example b51 Synthesis of lauryloxypolypropylene glycol (29) polyethylene glycol (15) monochloroacetate]
- 653 g of polyether a51 obtained in Synthesis Example a51 monochloroacetic acid (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) 35.1 g
- p -Toluenesulfonic acid monohydrate manufactured by Kishida Chemical Co., Ltd., special grade reagent
- the flask was purged with nitrogen, and reacted for 16 hours at 140 ° C. under a reduced pressure of ⁇ 0.1 MPaG while blowing nitrogen.
- the pressure was returned to atmospheric pressure with nitrogen, cooled to 80 ° C., 26.8 g of anhydrous sodium carbonate (manufactured by Kishida Chemical Co., Ltd., special grade reagent) was added, and the mixture was stirred at 80 ° C. for 2 hours.
- the obtained liquid was filtered with a filter paper (“No. 5A” manufactured by Advantech Toyo Co., Ltd.) to obtain lauryloxypolypropylene glycol (29) polyethylene glycol (15) monochloroacetate (chloroacetate b51).
- Synthesis Example c2 Synthesis of poly tertiary amine glycol (average number of amine functional groups: 3.7)]
- a 1 L flask equipped with a condenser and a separator for separating reaction water was charged with 600 g of 1,6-hexanediol and 12 g of a Cu—Ni catalyst (“MX-2141” manufactured by Kao Corporation). While stirring, the inside of the system was replaced with nitrogen, and the temperature was raised. Simultaneously with the start of temperature increase, hydrogen gas was blown into the reaction system at a flow rate of 30 L / hr, and the temperature was increased to 185 ° C. over about 40 minutes.
- Dispersant 1 containing the following compound 1-1 as a main component was obtained.
- the methyl group (s) corresponds to R 1 in the formula (1)
- the single bond (t) corresponds to R 5 adjacent to R 1 in the formula (1), that is, a single bond.
- Dispersants 2 to 14, 17, and 19 to 21 were obtained in the same manner as in Production Example 1 except that chloroacetate, polyamine, and PGMEA shown in Table 3 below were used.
- the structure of the dispersant obtained in this Production Example is shown in Table 4 by applying it to the formula (1) in this specification.
- the raw materials used in the table are as follows.
- Polyamine c4 N, N-dimethylaminohexanol, manufactured by Kao Corporation “Caorizer No. 25”
- Polyamine c5 N, N, N ′, N ′′, N ′′ -pentamethyldipropylenetriamine, “Polycat 77” manufactured by Air Products Japan Ltd.
- Dispersants 16 and 18 were obtained in the same manner as in Production Example 15 except that chloroacetate, polyamine, PGMEA and quaternizing agent described in Table 3 below were used.
- Dispersant 2 is composed mainly of the following compound 1-2.
- the methyl group (s) corresponds to R 1 in the formula (1), and (t) corresponds to R 5 adjacent to R 1 in the formula (1), that is, a single bond.
- the signals derived from the methyl group and the methylene group bonded to N of the polyamine c1 are changed from 2.2, 2.3 ppm, respectively, to 3.3, 3.2 ppm, and further from N, depending on the reaction.
- the signal derived from a distant methylene group shifted from 1.6 ppm to 2.2 ppm.
- Dispersant 3 is composed mainly of the following compound 1-3.
- the hydroxyhexyl group (u) corresponds to R 1 in the formula (1)
- (t) corresponds to R 5 adjacent to R 1 in the formula (1), that is, a single bond.
- the example in which the amine moiety at the terminal of the polyamine is not quaternized is shown, but the arrangement of each structural unit may be any.
- the transition of the following peaks was confirmed by the reaction. Signals derived from a methyl group and a methylene group bonded to N of polyamine c2 shifted from 2.2 and 2.3 ppm to 3.4 and 3.2 ppm, respectively.
- the signal derived from the methylene group bonded to chlorine in chloroacetate b1 shifted from 4.1 ppm to 4.4 ppm.
- Dispersant 4 is composed mainly of the following compound 1-4.
- the hydroxyhexyl group (u) corresponds to R 1 in the formula (1)
- (t) corresponds to R 5 adjacent to R 1 in the formula (1), that is, a single bond.
- the example in which the amine moiety at the terminal of the polyamine is not quaternized is shown, but the arrangement of each structural unit may be any.
- the transition of the following peaks was confirmed by the reaction. Signals derived from the methyl group and methylene group bonded to N of polyamine c3 shifted from 2.2 and 2.3 ppm to 3.4 and 3.2 ppm, respectively.
- the signal derived from the methylene group bonded to chlorine in chloroacetate b1 shifted from 4.1 ppm to 4.4 ppm.
- Dispersant 5 is composed mainly of the following compound 1-5.
- Dispersant 6 is composed mainly of the following compound 1-6.
- Dispersant 7 is composed mainly of the following compound 1-7.
- Dispersant 8 is composed mainly of the following compound 1-8.
- Dispersant 9 is composed mainly of the following compound 1-9.
- the dispersant 10 contains the following compound 1-10 as a main component.
- methyl group (s) corresponds to R 1 in formula (1)
- (t) corresponds to R 5 adjacent to R 1 in formula (1), ie, a single bond.
- the ⁇ -caprolactone units and ⁇ -valerolactone units are randomly arranged.
- Dispersant 11 is composed mainly of the following compound 1-11.
- methyl group (s) corresponds to R 1 in formula (1)
- (t) corresponds to R 5 adjacent to R 1 in formula (1), ie, a single bond.
- the ⁇ -caprolactone units and ⁇ -valerolactone units are randomly arranged.
- the dispersant 12 contains the following compound 1-12 as a main component.
- methyl group (s) corresponds to R 1 in formula (1)
- (t) corresponds to R 5 adjacent to R 1 in formula (1), ie, a single bond.
- the ⁇ -caprolactone units and ⁇ -valerolactone units are randomly arranged.
- Dispersant 13 is composed mainly of the following compound 1-13.
- the dispersant 14 contains the following compound 1-14 as a main component.
- Dispersant 15 is composed mainly of the following compound 1-15.
- the dispersant 16 contains the following compound 1-16 as a main component.
- Dispersant 17 is composed mainly of the following compound 1-17.
- Dispersant 18 is composed mainly of the following compound 1-18.
- Dispersants 19 to 21 contain the following compound 1-19.
- the reaction rate Cl was 94 mol%, n was 2.0, m was 0.0, and k was 0.0.
- V-65 2,2-azobis- ( 2,4-dimethylvalerontonyl)
- V-65 2,4-dimethylvalerontonyl
- a solution prepared by dissolving 2.0 g of V-65 in 10.0 g of PGMEA was added, and stirring was continued for 1 hour.
- a solution obtained by further dissolving 1.0 g of V-65 in 10.0 g of PGMEA was added, and stirring was continued for 1 hour.
- ASR1 BzMA / MAA copolymer having a molar ratio of 70/30.
- the solid content of the solution was 50% by mass, the acid value of ASR1 was 190 mgKOH / g, and the weight average molecular weight was 14,000 (measured value under ⁇ Condition 2>).
- DPP pigment DPP-1: “Irgaphor Red S 3621 CF” manufactured by BASF
- DPP-2 “Hostaperm Red D2B-COF01 LV3916” manufactured by Clariant
- DPP-3 “PIGMENT RED 5414” manufactured by Sanyo Dyeing Co., Ltd.
- DPHA Polyfunctional monomer
- Example 1 [Preparation of Pigment Dispersion 1] DPP-1 16.6 g, DPP-2 2.93 g, 1,3-phenylene dimaleimide (hereinafter also referred to as “PDM”) 0.98 g, Dispersant 1 solution 19.6 g obtained in Production Example 1 (solid 7.8 g), 11.7 g of 50% by mass PGMEA solution of ASR1 obtained in Synthesis Example AS1, 98.2 g of PGMEA, and 300 g of zirconia beads having a particle diameter of 0.2 mm were placed in a 500 mL plastic container, After dispersion (preliminary dispersion) for 3 hours by “Paint Shaker” manufactured by Iron Works Co., Ltd., zirconia beads were removed by filtration.
- PDM 1,3-phenylene dimaleimide
- Examples 2 to 4, 20 to 25, Comparative Examples 1 to 3 [Preparation of pigment dispersions 2 to 4, 20 to 25, 51 to 53, coloring compositions 2 to 4, 20 to 25, 51 to 53]
- Dispersant 1 was replaced with the dispersant shown in Table 5 in an amount such that the solid content of each dispersant solution was 7.8 g, and other operations were performed in the same manner as in Example 1 and described in Table 5 below.
- Pigment dispersions 2 to 4, 20 to 25, 51 to 53, and coloring compositions 2 to 4, 20 to 25, and 51 to 53 shown in Table 6 below were obtained.
- Dispersant 1 was replaced with the dispersant shown in Table 5, respectively, and DPP-1 16.6 g and DPP-2 2.93 g were changed to DPP-1 5.85 g and DPP-3 13.7 g.
- the solid content was 7.8 g, and the other operations were the same as in Example 1, and pigment dispersions 5 to 19, 54 and colored compositions 5 to 19, 54 shown in Table 6 below were obtained. .
- the pigment dispersions and coloring compositions of Examples 1 to 25 using the quaternary ammonium salt compounds of Production Examples 1 to 21 as dispersants were used without using the dispersant of the present invention.
- the average particle diameter after storage is small, and good developability and heat resistance are obtained. Therefore, the quaternary ammonium salt compound of the present invention is useful as a dispersant in a pigment dispersion, and the pigment dispersion and coloring composition using the compound have a small average particle diameter, low viscosity, and storage stability. In addition, it is understood that the developability and heat resistance are excellent.
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Abstract
L'invention concerne : un dispersant permettant d'obtenir une dispersion de pigment et une composition colorante, chacune d'elles présente un diamètre moyen de particule faible, une viscosité faible, une excellente stabilité au stockage et une excellente résistance à la chaleur ; une dispersion de pigment et une composition colorante, qui utilisent chacune ce dispersant ; et un filtre coloré qui est produit au moyen de cette composition colorante. [1] Un dispersant qui a un motif structurel A représenté par la formule (A) dans la structure moléculaire, et dans lequel le nombre moyen de motif structurel A contenu dans chaque structure moléculaire est de 1,0 à 22,0 (inclus) [2] Une dispersion de pigment pour filtres colorés, qui contient un dispersant décrit en [1], un pigment organique et un solvant organique [3] Un filtre coloré qui est produit à l'aide d'une composition colorée pour filtres colorés décrite en [2] [4] Un procédé de production d'un dispersant, qui comprend une étape 1, un composé représenté par la formule (3) étant mis à réagir avec un composé polyamine qui a un motif structurel B représenté par la formule (B) dans la structure moléculaire, et le nombre moyen de motif structurel B contenu dans chaque structure moléculaire étant de 1,0 à 22,0 (inclus) [5] Un composé sel d'ammonium quaternaire représenté par la formule (1).
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021153699A1 (fr) | 2020-01-30 | 2021-08-05 | 花王株式会社 | Composite de fibres de cellulose |
| WO2022130773A1 (fr) | 2020-12-17 | 2022-06-23 | 富士フイルム株式会社 | Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge |
| WO2022131191A1 (fr) | 2020-12-16 | 2022-06-23 | 富士フイルム株式会社 | Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges |
| WO2022172607A1 (fr) * | 2021-02-12 | 2022-08-18 | 昭和電工株式会社 | Agent dispersant polymère, composition de dispersion de pigment et composition colorée photosensible |
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| CN104285167B (zh) * | 2012-07-12 | 2017-03-01 | 花王株式会社 | 滤色器用颜料分散体及其制造方法和用途、滤色器用着色组合物及其用途、滤色器 |
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- 2015-12-25 CN CN201580071122.2A patent/CN107109076B/zh active Active
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021153699A1 (fr) | 2020-01-30 | 2021-08-05 | 花王株式会社 | Composite de fibres de cellulose |
| WO2022131191A1 (fr) | 2020-12-16 | 2022-06-23 | 富士フイルム株式会社 | Composition, membrane, filtre optique, élément de capture d'image solide, appareil d'affichage d'image et capteur de rayons infrarouges |
| WO2022130773A1 (fr) | 2020-12-17 | 2022-06-23 | 富士フイルム株式会社 | Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image et capteur infrarouge |
| WO2022172607A1 (fr) * | 2021-02-12 | 2022-08-18 | 昭和電工株式会社 | Agent dispersant polymère, composition de dispersion de pigment et composition colorée photosensible |
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| TW201628703A (zh) | 2016-08-16 |
| JPWO2016104803A1 (ja) | 2017-10-12 |
| KR20170100531A (ko) | 2017-09-04 |
| JP6645000B2 (ja) | 2020-02-12 |
| KR102456207B1 (ko) | 2022-10-18 |
| CN107109076A (zh) | 2017-08-29 |
| CN107109076B (zh) | 2019-12-31 |
| TWI680011B (zh) | 2019-12-21 |
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