JP6567905B2 - ブロック共重合体、分散剤及び顔料分散組成物 - Google Patents
ブロック共重合体、分散剤及び顔料分散組成物 Download PDFInfo
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- JP6567905B2 JP6567905B2 JP2015139446A JP2015139446A JP6567905B2 JP 6567905 B2 JP6567905 B2 JP 6567905B2 JP 2015139446 A JP2015139446 A JP 2015139446A JP 2015139446 A JP2015139446 A JP 2015139446A JP 6567905 B2 JP6567905 B2 JP 6567905B2
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- 239000000049 pigment Substances 0.000 title claims description 124
- 239000006185 dispersion Substances 0.000 title claims description 67
- 239000000203 mixture Substances 0.000 title claims description 67
- 229920001400 block copolymer Polymers 0.000 title claims description 56
- 239000002270 dispersing agent Substances 0.000 title claims description 18
- 239000000178 monomer Substances 0.000 claims description 78
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 54
- 229920002554 vinyl polymer Polymers 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000001302 tertiary amino group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000002612 dispersion medium Substances 0.000 claims description 9
- 229920000359 diblock copolymer Polymers 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 57
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 52
- -1 acryl Chemical group 0.000 description 41
- 229920001577 copolymer Polymers 0.000 description 39
- 238000000034 method Methods 0.000 description 36
- 238000006116 polymerization reaction Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- 239000002585 base Substances 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 23
- 238000000576 coating method Methods 0.000 description 23
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 229920005989 resin Polymers 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000003513 alkali Substances 0.000 description 18
- 239000011230 binding agent Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 17
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 12
- 239000011259 mixed solution Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 230000000379 polymerizing effect Effects 0.000 description 11
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000010526 radical polymerization reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 9
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- SRLROPAFMUDDRC-INIZCTEOSA-N ethyl N-benzoyl-L-tyrosinate Chemical compound C([C@@H](C(=O)OCC)NC(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 SRLROPAFMUDDRC-INIZCTEOSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 150000003498 tellurium compounds Chemical class 0.000 description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007869 azo polymerization initiator 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 6
- JPIIVHIVGGOMMV-UHFFFAOYSA-N ditellurium Chemical compound [Te]=[Te] JPIIVHIVGGOMMV-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 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 6
- 238000004448 titration Methods 0.000 description 6
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000008034 disappearance Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 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 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001400 nonyl 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])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- ONDSSKDTLGWNOJ-UHFFFAOYSA-N 1-methoxyhexan-2-ol Chemical compound CCCCC(O)COC ONDSSKDTLGWNOJ-UHFFFAOYSA-N 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 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
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- 101710141544 Allatotropin-related peptide Proteins 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
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Description
本発明のブロック共重合体は、2種以上のビニルモノマーを用いて重合された共重合体である。具体的には後述する一般式(1)で表わされる構造単位を含むAブロックと、3級アミノ基を有するビニルモノマーに由来する構造単位及び4級アンモニウム塩基を有するビニルモノマーに由来する構造単位を含むBブロックとを有し、アミン価が20〜150mgKOH/gであることを特徴としている。該Aブロックは「Aセグメント」、及びBブロックは「Bセグメント」と言い換えることもできる。
Aブロックは、下記一般式(1)で表わされる構造単位を含むポリマーブロックである。
Bブロックは、3級アミノ基を有するビニルモノマーに由来する構造単位及び4級アンモニウム塩基を有するビニルモノマーに由来する構造単位を含むポリマーブロックである。
ブロック共重合体のアミン価は、20〜150mgKOH/gである。ブロック共重合体のアミン価がこの範囲になるように、Bブロックに3級アミノ基を有するビニルモノマーに由来する構造単位が含まれていることが好ましい。ブロック共重合体のアミン価の下限値は、30mgKOH/gであることが好ましく、40mgKOH/gであることがより好ましい。ブロック共重合体のアミン価の上限値は、120mgKOH/gであることが好ましく、100mgKOH/gであることがより好ましい。
本発明のブロック共重合体の製造方法は、特に限定はなく、例えばリビングラジカル重合法等のブロック重合法が挙げられる。本発明のブロック共重合体は、該ブロック重合法によって、ブロックを構成するモノマーを順次重合反応させることにより得られる。
(b)一般式(5)で表される有機テルル化合物とアゾ系重合開始剤の混合物、
(c)一般式(5)で表される有機テルル化合物と一般式(6)で表される有機ジテルル化合物の混合物、又は
(d)一般式(5)で表される有機テルル化合物、アゾ系重合開始剤及び一般式(6)で表される有機ジテルル化合物の混合物、
のいずれかを用いて重合する。
本実施形態に係る顔料分散組成物は、上記のブロック共重合体を含有する分散剤と顔料及び分散媒体とを含む。顔料分散組成物は、バインダー樹脂等を含んでいてもよい。
NMR(商品名:AVANCE500、ブルカー・バイオスピン社製)を用いて、1H−NMRを測定し、モノマーのビニル基とポリマーのエステル側鎖のピーク面積比から重合率を算出した。
GPC(商品名:HLC−8320GPC、東ソー社製、カラム:TSKgel α−3000、移動相:10mMリチウムブロミド/ジメチルホルムアミド溶液)を用い、標準物質としてポリスチレン(分子量427,000、190,000、96,400、37,400、10,200、2,630、440、92)を使用して検量線を作成し、重量平均分子量(Mw)、数平均分子量(Mn)を測定した。この測定値から、分子量分布(PDI=Mw/Mn)を算出した。
アミン価は、固形分1gあたりの塩基性成分と当量の水酸化カリウムの質量で表わしたものである。測定サンプルをテトラヒドロフランに溶解し、電位差滴定装置(商品名:GT−06、三菱化学社製)を用いて、得られた溶液を0.1M塩酸/2−プロパノール溶液で中和滴定した。滴定pH曲線の変曲点を滴定終点として次式によりアミン価(B)を算出した。
B:アミン価(mgKOH/g)
Vs:滴定に要した0.1M塩酸/2−プロパノール溶液の使用量(mL)
f:0.1M塩酸(2−プロパノール性)の力価
w:測定サンプルの質量(g)(固形分換算)
酸価は、固形分1gあたりの酸性成分を中和するのに要する水酸化カリウムの重量を表わしたものである。測定サンプルをテトラヒドロフランに溶解し、電位差滴定装置(商品名:GT−06、三菱化学社製)を用いて、得られた溶液を0.1M水酸化カリウム/2−プロパノール溶液で中和滴定した。滴定pH曲線の変曲点を滴定終点として、次式により酸価(A)を算出した。
A:酸価(mgKOH/g)
Vs:滴定に要した0.1M水酸化カリウム/2−プロパノール溶液の使用量(mL)
f:0.1M水酸化カリウム(2−プロパノール性)の力価
w:測定サンプル質量(g)(固形分換算)
顔料分散組成物の製造直後と、40℃で7日間静置したものを、それぞれE型粘度計(商品名:TVE−22L、東機産業社製)を用い、1°34’×R24のコーンローターを使用して、25℃下、ローター回転数60rpmで粘度を測定した。その粘度変化を以下の基準により評価した。
B:粘度変化が+200%未満
C:粘度変化が+200%以上
表面を洗浄した50mm×30mmのガラス板上に、2μmの厚さで顔料分散組成物を塗布し、90℃で10分間乾燥して塗布膜を形成した。次に、ガラス板を溶剤(プロピレングリコールモノメチルエーテルアセテート)に浸漬し、塗布膜の溶剤への溶解性を観察した。その溶解性を以下の基準により評価した。
B:浸漬10分未満に塗布膜がガラス板上から溶離している。
C:浸漬10分後に塗布膜がガラス板上に残っている。
表面を洗浄した50mm×30mmのガラス板上に、2μmの厚さで顔料分散組成物の塗布膜を形成し、90℃で10分間乾燥した。次に、塗布膜を形成したガラス板を1%水酸化カリウム水溶液に浸漬し、塗布膜の1%水酸化カリウム水溶液(アルカリ水溶液)中への溶解性を観察した。その溶解性を以下の基準により評価した。
B:浸漬3分未満に塗布膜がガラス板上から溶離している。
C:浸漬3分後に塗布膜がガラス板上に残っている。
(実施例1)共重合体Aの製造
アルゴンガス導入管、撹拌機を備えたフラスコにメタクリル酸2−ヒドロキシエチルのカプロラクトン5mol付加物(商品名:プラクセルFM5、ダイセル化学社製、以下「PCL5」という)3.18g、メタクリル酸n−ブチル(商品名:アクリエステルB、三菱レイヨン社製、以下「BMA」という)2.31g、メタクリル酸(商品名:メタクリル酸MAA、三菱レイヨン社製、以下「MAA」という)0.23g、アゾビスイソブチニトリル(商品名:AIBN、大塚化学社製、以下「AIBN」という)0.0328g、プロピレングリコールモノメチルエーテルアセテート(以下「PMA」という)3.81gを仕込み、アルゴン置換後、エチル−2−メチル−2−n−ブチルテラニル−プロピオネート(以下「BTEE」という)0.30g、ジブチルジテルリド(以下「DBDT」という)0.18gを加え、60℃で12時間反応させた。重合率は98%であった。
アルゴンガス導入管、撹拌機を備えたフラスコにPCL5 3.18g、BMA 2.31g、MAA 0.23g、AIBN 0.0328g、PMA 3.81gを仕込み、アルゴン置換後、BTEE 0.30g、DBDT 0.18gを加え、60℃で16時間反応させた。重合率は99%であった。
アルゴンガス導入管、撹拌機を備えたフラスコにPCL5 4.10g、BMA 3.00g、MAA 0.30g、AIBN 0.0328g、PMA 4.93gを仕込み、アルゴン置換後、BTEE 0.30g、DBDT 0.18gを加え、60℃で25時間反応させた。重合率は100%であった。
アルゴンガス導入管、撹拌機を備えたフラスコにPCL5 4.10g、BMA 3.00g、MAA 0.30g、AIBN 0.0328g、PMA 4.93gを仕込み、アルゴン置換後、BTEE 0.30g、DBDT 0.18gを加え、60℃で19時間反応させた。重合率は100%であった。
アルゴンガス導入管、撹拌機を備えたフラスコにPCL5 4.10g、BMA 3.00g、MAA 0.30g、AIBN 0.0328g、PMA 4.93gを仕込み、アルゴン置換後、BTEE 0.30g、DBDT 0.18gを加え、60℃で12時間反応させた。重合率は97%であった。
アルゴンガス導入管、撹拌機を備えたフラスコにPCL5 3.18g、BMA 2.31g、MAA 0.23g、AIBN 0.0328g、PMA 3.81gを仕込み、アルゴン置換後、BTEE 0.30g、DBDT 0.18gを加え、60℃で20時間反応させた。重合率は99%であった。
アルゴンガス導入管、撹拌機を備えたフラスコにトリエチレングリコールモノエチルエーテルモノメタクリレート(POLYSCIENCES社製)0.80g、BMA 3.70g、メタクリル酸メチル(三菱レイヨン社製)2.40g、メタクリル酸2−エチルヘキシル(三菱レイヨン社製)2.20g、AIBN 0.0328g、PMA 6.07gを仕込み、アルゴン置換後、BTEE 0.30g、DBDT 0.18gを加え、60℃で16時間反応させた。重合率は99%であった。
顔料10質量部、分散剤3質量部、バインダー樹脂{メタクリル酸ベンジル/メタクリル酸=80/20の質量比で重合させたもの、Mw=9800、PDI=1.93、酸価127mgKOH/g、固形分40質量%のPMA溶液}3質量部、メトキシプロパノール10質量部、及びPMA 74質量部となるように配合を調整し、遊星ボールミル(0.3mmジルコニアビーズ、2時間)で撹拌して、表1〜2に示す実施例6〜10及び比較例3〜4の顔料分散組成物を得た。分散剤としては、実施例1〜5及び比較例1〜2で得た共重合体A〜Gを用い、顔料にはC.I.Pigment Red 177(商品名:FASTGEN SuperRed ATY、DIC社製)又はC.I.Pigment Green 58(商品名:FASTOGEN Green A110、DIC社製)を用いた。
Claims (6)
- 下記一般式(1)で表わされる構造単位を含むAブロックと、3級アミノ基を有するビニルモノマーに由来する構造単位及び4級アンモニウム塩基を有するビニルモノマーに由来する構造単位を含むBブロックとを有し、アミン価が20〜150mgKOH/gであり、
前記3級アミノ基を有するビニルモノマーに由来する構造単位が、下記一般式(2)で表され、
前記4級アンモニウム塩基を有するビニルモノマーに由来する構造単位が、下記一般式(3)で表され、
前記3級アミノ基及び前記4級アンモニウム塩基の合計モル当量数に対する、前記4級アンモニウム塩基のモル当量数の割合が、5〜60mol%である、ブロック共重合体。
- 前記Aブロックの含有量が、ブロック共重合体全体100質量%中において50〜95質量%である、請求項1に記載のブロック共重合体。
- 前記Aブロックと前記Bブロックとからなるジブロック共重合体である、請求項1又は2に記載のブロック共重合体。
- 請求項1〜3のいずれか一項に記載のブロック共重合体を含有する、分散剤。
- 請求項4に記載の分散剤と、顔料及び分散媒体とを含む、顔料分散組成物。
- カラーフィルタ用である、請求項5に記載の顔料分散組成物。
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