JP5495416B2 - Non-aqueous pigment dispersant and pigment composition - Google Patents
Non-aqueous pigment dispersant and pigment composition Download PDFInfo
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- JP5495416B2 JP5495416B2 JP2008331669A JP2008331669A JP5495416B2 JP 5495416 B2 JP5495416 B2 JP 5495416B2 JP 2008331669 A JP2008331669 A JP 2008331669A JP 2008331669 A JP2008331669 A JP 2008331669A JP 5495416 B2 JP5495416 B2 JP 5495416B2
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- pigment dispersant
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- 239000000049 pigment Substances 0.000 title claims description 70
- 239000002270 dispersing agent Substances 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 title claims description 43
- -1 diol compound Chemical class 0.000 claims description 158
- 239000000126 substance Substances 0.000 claims description 83
- 150000001491 aromatic compounds Chemical class 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000000962 organic group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 229920000728 polyester Polymers 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 15
- 238000006068 polycondensation reaction Methods 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000003125 aqueous solvent Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000012860 organic pigment Substances 0.000 claims description 2
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- 238000003786 synthesis reaction Methods 0.000 description 20
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- 239000002245 particle Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 10
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
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- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 229910017052 cobalt Inorganic materials 0.000 description 3
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
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- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 3
- 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 3
- 125000006410 propenylene group Chemical group 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
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- AUQIXRHHSITZFM-UHFFFAOYSA-N 11-phenylundecanoic acid Chemical compound OC(=O)CCCCCCCCCCC1=CC=CC=C1 AUQIXRHHSITZFM-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- UMUCFVZOWBFZEJ-UHFFFAOYSA-N acetic acid;anthracene Chemical compound CC(O)=O.C1=CC=CC2=CC3=CC=CC=C3C=C21 UMUCFVZOWBFZEJ-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 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
- 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
- AWIZFKXFPHTRHN-UHFFFAOYSA-N naphtho[2,3-f]quinoline Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 AWIZFKXFPHTRHN-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 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 1
- 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 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 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 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 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 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Description
本発明は、非水系顔料分散剤及び顔料組成物に関する。非水系溶媒中に顔料を分散させる場合、その分散工程で分散剤を分散浴に投入するが、この際に良好な作業性を得るため、また優れた塗膜を得るため、投入した顔料が分散浴中に速やかに均一分散してその分散状態が安定して維持されること、また得られる塗膜に色調のばらつきが少ないことが要求される。特に近年のように、より優れた色再現性を有する塗膜を得るため、顔料として粒子径が数百ｎｍ以下の微粒子のものを用いる場合においては、上記の要求が更に強い。本発明はかかる要求に応える非水系顔料分散剤及びこれを用いた顔料組成物に関する。 The present invention relates to a non-aqueous pigment dispersant and a pigment composition. When dispersing the pigment in a non-aqueous solvent, the dispersing agent is added to the dispersion bath in the dispersion step. At this time, in order to obtain good workability and an excellent coating film, the added pigment is dispersed. It is required that the dispersion is quickly and uniformly dispersed in the bath and the dispersion state is stably maintained, and that the obtained coating film has little variation in color tone. In particular, as in recent years, in order to obtain a coating film having more excellent color reproducibility, the above-described demand is further increased when a pigment having a particle diameter of several hundred nm or less is used as a pigment. The present invention relates to a non-aqueous pigment dispersant that meets such requirements and a pigment composition using the same.
従来、前記のような非水系顔料分散剤としては、例えば、１）ポリカルボン酸とポリオールとを構成単位とし且つ該ポリオールの５０重量％以上がビスフェノールのアルキレンオキシド付加物であるポリエステル樹脂（例えば特許文献１参照）、２）二価カルボン酸とポリエチレングリコールとの縮合物を一価アルコールでエステル化したもの（例えば特許文献２参照）、３）アミノ基と反応する官能基を有する有機色素とアミンを反応させたもの（例えば特許文献３参照）、４）芳香族環にポリエーテルを結合したもの（例えば特許文献４参照）、５）テトラカルボン酸化合物にポリカプロラクトンを結合したもの（例えば特許文献５参照）等が提案されている。 Conventionally, as the non-aqueous pigment dispersant as described above, for example, 1) a polyester resin having polycarboxylic acid and polyol as constituent units and 50% by weight or more of the polyol is an alkylene oxide adduct of bisphenol (for example, patent) 2) A product obtained by esterifying a condensate of a divalent carboxylic acid and polyethylene glycol with a monohydric alcohol (see, for example, Patent Document 2), 3) an organic dye and an amine having a functional group that reacts with an amino group (For example, see Patent Document 3), 4) a polyether bonded to an aromatic ring (see, for example, Patent Document 4), 5) a tetracarboxylic acid compound to which polycaprolactone is bonded (for example, Patent Document) 5)) has been proposed.
ところが、かかる従来の非水系顔料分散剤には、もともと分散性が不充分であったり、また当初は相応の分散性を示してもそれが安定して維持されなかったり、更には分散剤の量のわずかな変動によって得られる塗膜の色調がばらついたりする等の問題がある。
本発明が解決しようとする課題は、良好な分散性を示し、またそれが安定維持され、更に得られる塗膜が色調の再現性に優れる非水系顔料分散剤及び顔料組成物を提供する処にある。 The problem to be solved by the present invention is to provide a non-aqueous pigment dispersant and a pigment composition that exhibit good dispersibility, that are stably maintained, and that the resulting coating film has excellent color tone reproducibility. is there.
しかして本発明者らは、前記の問題を解決するべく研究した結果、かかる非水系顔料分散剤としては、特定の三成分を重縮合したポリエステルから成るものを用いるのが正しく好適であることを見出した。 Accordingly, as a result of studies conducted by the present inventors to solve the above-mentioned problems, it is found that it is correctly preferable to use a non-aqueous pigment dispersant made of polyester obtained by polycondensation of specific three components. I found it.
すなわち本発明は、下記のＡ成分、Ｂ成分及びＣ成分を重縮合したポリエステルから成ることを特徴とする非水系顔料分散剤に係る。 That is, the present invention relates to a non-aqueous pigment dispersant characterized by comprising a polyester obtained by polycondensation of the following A component, B component and C component.
Ａ成分：下記の化１で示される芳香族化合物 Component A: aromatic compound represented by the following chemical formula 1
化１において、
Ｘ：アリール基
Ｙ：下記の化２で示される有機基、化３で示される有機基、化４で示される有機基又は化５で示される有機基
In chemical formula 1,
X: aryl group Y: organic group represented by the following chemical formula 2, organic group represented by chemical formula 3, organic group represented by chemical formula 4 or organic group represented by chemical formula 5
化２〜化５において、
Ｚ１，Ｚ２：水素原子又は炭素数１〜１２のアルキル基
Ｒ１，Ｒ２：炭素数１〜１２の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
Ｒ３：炭素数２〜４の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
ｍ：１〜３の整数
In Chemical Formulas 2 to 5,
Z 1 , Z 2 : a hydrogen atom or an alkyl group having 1 to 12 carbon atoms R 1 , R 2 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 12 carbon atoms R 3 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 2 to 4 carbon atoms m: an integer of 1 to 3
Ｂ成分：下記の化６で示される化合物及び化７で示される化合物から選ばれる一つ又は二つ以上。 Component B: One or more selected from the compound represented by the following chemical formula 6 and the compound represented by the chemical formula 7.
化６及び化７において、
Ｒ４：炭素数１〜１６の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
Ｚ３，Ｚ４，Ｚ５，Ｚ６：水素原子又は炭素数１〜１２のアルキル基
In Chemical Formula 6 and Chemical Formula 7,
R 4 : residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 16 carbon atoms Z 3 , Z 4 , Z 5 , Z 6 : hydrogen atom or 1 to 12 carbon atoms Alkyl group
Ｃ成分：下記の化８で示されるジオール化合物。 Component C: a diol compound represented by the following chemical formula 8.
化８において、
Ｒ５：炭素数１〜１８の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
In chemical formula 8,
R 5 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 18 carbon atoms
また本発明は、顔料、非水系溶媒、バインダー樹脂及び前記した本発明に係る非水系顔料分散剤を含有してなることを特徴とする顔料組成物に係る。 The present invention also relates to a pigment composition comprising a pigment, a non-aqueous solvent, a binder resin, and the non-aqueous pigment dispersant according to the present invention.
先ず、本発明に係る非水系顔料分散剤（以下、単に本発明の分散剤という）について説明する。本発明の分散剤は、Ａ成分、Ｂ成分及びＣ成分を重縮合したポリエステルから成るものである。 First, the non-aqueous pigment dispersant according to the present invention (hereinafter simply referred to as the dispersant of the present invention) will be described. The dispersant of the present invention comprises a polyester obtained by polycondensation of A component, B component and C component.
本発明の分散剤となるポリエステルに供するＡ成分は、化１で示される芳香族化合物である。かかる芳香族化合物において、化１中のＸは芳香族炭化水素環の任意の位置の水素原子を１個除いたアリール基である。かかるアリール基は炭素数６〜３２のものが好ましい。具体的にＸとしては、フェニル基、ナフチル基、アントラセニル基、フェナントレニル基、トリフェニレニル基、ピレニル基、クリセニル基、ナフタセニル基、ペリレニル基、テトラフェニレニル基、ペンタフェニル基、ペンタセニル基、コロネニル基、ヘキサフェニル基、ヘキサセニル基、ヘプタセニル基等が挙げられる。なかでもナフチル基又はアントラセニル基が好ましい。 The component A to be used for the polyester as the dispersant of the present invention is an aromatic compound represented by Chemical Formula 1. In such an aromatic compound, X in Chemical Formula 1 is an aryl group obtained by removing one hydrogen atom at an arbitrary position of the aromatic hydrocarbon ring. Such aryl groups preferably have 6 to 32 carbon atoms. Specifically, as X, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, perylenyl group, tetraphenylenyl group, pentaphenyl group, pentacenyl group, coronenyl group, A hexaphenyl group, a hexacenyl group, a heptacenyl group, etc. are mentioned. Of these, a naphthyl group or an anthracenyl group is preferable.
化１で示される芳香族化合物において、化１中のＹは、化２で示される有機基、化３で示される有機基、化４で示される有機基又は化５で示される有機基である。 In the aromatic compound represented by chemical formula 1, Y in chemical formula 1 is an organic group represented by chemical formula 2, an organic group represented by chemical formula 3, an organic group represented by chemical formula 4 or an organic group represented by chemical formula 5. .
化２で示される有機基において、化２中のＺ１は水素原子又は炭素数１〜１２のアルキル基である。かかるＺ１としては、１）水素、２）メチル基、エチル基、プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｔ−ブチル基、ｎ−ペンチル基、イソペンチル基、ネオペンチル基、ヘキシル基、２−メチル−ペンチル基、ヘプチル基、１−メチルヘキシル基、３−メチルヘキシル基、４−メチルヘキシル基、５−メチルヘキシル基、１−エチルペンチル基、１−（ｎ−プロピル）ブチル基、１，１−ジメチルペンチル基、１，４−ジメチルペンチル基、１，１−ジエチルプロピル基、１，３，３−トリメチルブチル基、１−エチル−２，２−ジメチルプロピル基、１−イソプロピル−１，２−ジメチルプロピル基、オクチル基、１−メチルヘプチル基、５−メチルヘプチル基、１−エチルヘキシル基、２−エチルヘキシル基、１−プロピルペンチル基、２−プロピルペンチル基、１，１−ジメチルヘキシル基、１，４−ジメチルヘキシル基、１，５−ジメチルヘキシル基、１−エチル−１−メチルペンチル基、１−エチル−４−メチルペンチル基、１，１，４−トリメチルペンチル基、２，４，４−トリメチルペンチル基、２−エチル−ヘキシル基、２−プロピル−ヘプチル基、ノニル基、１−メチルオクチル基、６−メチルオクチル基、１−エチルヘプチル基、１−（ｎ−ブチル）ペンチル基、４−メチル−１−（ｎ−プロピル）ペンチル基、１，５，５−トリメチルヘキシル基、１，１，５−トリメチルヘキシル基、デシル基、１−メチルノニル基、１−エチルオクチル基、１−（ｎ−ブチル）ヘキシル基、１，１−ジメチルオクチル基、３，７−ジメチルオクチル基、ウンデシル基、１−メチルデシル基、１−エチルノニル基、ドデシル基、２−ブチル−オクチル基、１−メチルウンデシル基等の炭素数１〜１２のアルキル基が挙げられる。なかでも水素原子又はメチル基が好ましい。 In the organic group represented by Chemical Formula 2, Z 1 in Chemical Formula 2 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. Such Z 1 includes 1) hydrogen, 2) methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, hexyl group. 2-methyl-pentyl group, heptyl group, 1-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group, 1- (n-propyl) butyl group 1,1-dimethylpentyl group, 1,4-dimethylpentyl group, 1,1-diethylpropyl group, 1,3,3-trimethylbutyl group, 1-ethyl-2,2-dimethylpropyl group, 1-isopropyl -1,2-dimethylpropyl group, octyl group, 1-methylheptyl group, 5-methylheptyl group, 1-ethylhexyl group, 2-ethylhexyl group, 1- Propylpentyl group, 2-propylpentyl group, 1,1-dimethylhexyl group, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group, 1-ethyl-1-methylpentyl group, 1-ethyl-4- Methylpentyl group, 1,1,4-trimethylpentyl group, 2,4,4-trimethylpentyl group, 2-ethyl-hexyl group, 2-propyl-heptyl group, nonyl group, 1-methyloctyl group, 6-methyl Octyl group, 1-ethylheptyl group, 1- (n-butyl) pentyl group, 4-methyl-1- (n-propyl) pentyl group, 1,5,5-trimethylhexyl group, 1,1,5-trimethyl Hexyl group, decyl group, 1-methylnonyl group, 1-ethyloctyl group, 1- (n-butyl) hexyl group, 1,1-dimethyloctyl group, 3,7-dimethyloctyl , Undecyl, 1-methyldecyl group, 1-Echirunoniru group, dodecyl group, 2-butyl - octyl group, an alkyl group having 1 to 12 carbon atoms such as 1-methyl-undecyl group. Of these, a hydrogen atom or a methyl group is preferable.
化３で示される有機基において、化３中のＺ２は水素原子又は炭素数１〜１２のアルキル基である。これについては、Ｚ１について前記したことと同じである。また化３中のＲ１は、炭素数１〜１２の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基である。かかるＲ１としては、１）メチレン基、エチレン基、トリメチレン基、メチルエチレン基、テトラメチレン基、エチルエチレン基、ペンタメチレン基、プロピルエチレン基、ヘキサメチレン基、２−メチル−ペンタメチレン基、ヘプタメチレン基、１−メチルヘキサメチレン基、３−メチルヘキサメチレン基、４−メチルヘキサメチレン基、５−メチルヘキサメチレン基、１−エチルペンタメチレン基、１−（ｎ−プロピル）テトラメチレン基、１，１−ジメチルペンタメチレン基、１，４−ジメチルペンタメチレン基、１，１−ジエチルトリメチレン基、１，３，３−トリメチルテトラメチレン基、１−エチル−２，２−ジメチルトリメチレン基、１−イソプロピル−１，２−ジメチルトリメチレン基、オクタメチレン基、１−メチルヘプタメチレン基、５−メチルヘプタメチレン基、１−エチルヘキサメチレン基、２−エチルヘキサメチレン基、１−プロピルペンタメチレン基、２−プロピルペンタメチレン基、１，１−ジメチルヘキサメチレン基、１，４−ジメチルヘキサメチレン基、１，５−ジメチルヘキサメチレン基、１−エチル−１−メチルペンタメチレン基、１−エチル−４−メチルペンタメチレン基、１，１，４−トリメチルペンタメチレン基、２，４，４−トリメチルペンタメチレン基、２−エチル−ヘキサメチレン基、２−プロピル−ヘプタメチレン基、ノナメチレン基、１−メチルオクタメチレン基、６−メチルオクタメチレン基、１−エチルヘプタメチレン基、１−（ｎ−ブチル）ペンタメチレン基、４−メチル−１−（ｎ−プロピル）ペンタメチレン基、１，５，５−トリメチルヘキサメチレン基、１，１，５−トリメチルヘキサメチレン基、デカメチレン基、１−メチルノナメチレン基、１−エチルオクタメチレン基、１−（ｎ−ブチル）ヘキサメチレン基、１，１−ジメチルオクタメチレン基、３，７−ジメチルオクタメチレン基、ウンデカメチレン基、１−メチルデカメチレン基、１−エチルノナメチレン基、ドデカメチレン基、２−ブチル−オクタメチレン基、１−メチルウンデカメチレン基等の炭素数１〜１２のアルキレン基、２）ビニレン基、プロペニレン基、ブテニレン基、ペンテニレン基、ヘキセニレン基、ヘプテニレン基、１−メチル−２−ヘプテニレン基、オクテニレン基、３，７−ジメチル−６−オクテニレン基、２，７−オクタジエニレン基、１，１−ジ（２−プロペニル）エチレン基、ノネニレン基、２，６−ノナジエニレン基、デセニレン基、３，７−ジメチル−２，６−オクタジエニレン基、ウンデセニレン基、２，４−ウンデカジエニレン基、ドデセニレン基等の炭素数２〜１２のアルケニレン基、３）エチニレン基、プロピニレン基、ブチニレン基、ペンチニレン基等の炭素数２〜１２のアルキニレン基等が挙げられる。なかでも炭素数１〜１２のアルキレン基が好ましく、メチレン基、エチレン基、トリメチレン基、メチルエチレン基又はテトラメチレン基がより好ましく、メチレン基又はエチレン基が特に好ましい。 In the organic group represented by Chemical Formula 3, Z 2 in Chemical Formula 3 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. This is the same as described above for Z 1 . R 1 in Chemical Formula 3 is a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 12 carbon atoms. Examples of such R 1 include 1) methylene group, ethylene group, trimethylene group, methylethylene group, tetramethylene group, ethylethylene group, pentamethylene group, propylethylene group, hexamethylene group, 2-methyl-pentamethylene group, hepta Methylene group, 1-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 5-methylhexamethylene group, 1-ethylpentamethylene group, 1- (n-propyl) tetramethylene group, 1 , 1-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 1,1-diethyltrimethylene group, 1,3,3-trimethyltetramethylene group, 1-ethyl-2,2-dimethyltrimethylene group, 1-isopropyl-1,2-dimethyltrimethylene group, octamethylene group, 1-methylhept Tamethylene group, 5-methylheptamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 1,1-dimethylhexamethylene group, 1,4 -Dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1-ethyl-1-methylpentamethylene group, 1-ethyl-4-methylpentamethylene group, 1,1,4-trimethylpentamethylene group, 2, 4,4-trimethylpentamethylene group, 2-ethyl-hexamethylene group, 2-propyl-heptamethylene group, nonamethylene group, 1-methyloctamethylene group, 6-methyloctamethylene group, 1-ethylheptamethylene group, 1 -(N-butyl) pentamethylene group, 4-methyl-1- (n-propyl) pentamethylene group 1,5,5-trimethylhexamethylene group, 1,1,5-trimethylhexamethylene group, decamethylene group, 1-methylnonamethylene group, 1-ethyloctamethylene group, 1- (n-butyl) hexamethylene group, 1,1-dimethyloctamethylene group, 3,7-dimethyloctamethylene group, undecamethylene group, 1-methyldecamethylene group, 1-ethylnonamethylene group, dodecamethylene group, 2-butyl-octamethylene group, 1 -An alkylene group having 1 to 12 carbon atoms such as a methylundecamethylene group, 2) a vinylene group, a propenylene group, a butenylene group, a pentenylene group, a hexenylene group, a heptenylene group, a 1-methyl-2-heptenylene group, an octenylene group, 3 , 7-dimethyl-6-octenylene group, 2,7-octadienylene group, 1,1-di (2-pro Nyl) ethylene, nonenylene, 2,6-nonadienylene, decenylene, 3,7-dimethyl-2,6-octadienylene, undecenylene, 2,4-undecadienylene, dodecenylene, etc. 2-12 alkenylene groups, 3) C2-C12 alkynylene groups such as ethynylene group, propynylene group, butynylene group, pentynylene group and the like. Among these, an alkylene group having 1 to 12 carbon atoms is preferable, a methylene group, an ethylene group, a trimethylene group, a methylethylene group or a tetramethylene group is more preferable, and a methylene group or an ethylene group is particularly preferable.
化４で示される有機基において、化４中のＲ２は炭素数１〜１２の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基である。これについては、Ｒ１について前記したことと同じである。なかでも炭素数１〜１２のアルキレン基が好ましく、炭素数１〜５のアルキレン基がより好ましく、メチレン基又はエチレン基が特に好ましい。 In the organic group represented by Chemical formula 4, R 2 in Chemical formula 4 is a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 12 carbon atoms. This is the same as described above for R 1 . Among these, an alkylene group having 1 to 12 carbon atoms is preferable, an alkylene group having 1 to 5 carbon atoms is more preferable, and a methylene group or an ethylene group is particularly preferable.
化５で示される有機基において、化５中のＲ３は炭素数２〜４の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基である。かかるＲ３としては、エチレン基、トリメチレン基、メチルエチレン基、テトラメチレン基、エチルエチレン基等の炭素数２〜４のアルキレン基が挙げられる。なかでもエチレン基、メチルエチレン基又はエチルエチレン基が好ましく、エチレン基がより好ましい。また化５中のｍは１〜３の整数である。 In the organic group represented by Chemical Formula 5, R 3 in Chemical Formula 5 is a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 2 to 4 carbon atoms. Examples of R 3 include an alkylene group having 2 to 4 carbon atoms such as an ethylene group, a trimethylene group, a methylethylene group, a tetramethylene group, and an ethylethylene group. Of these, an ethylene group, a methylethylene group or an ethylethylene group is preferable, and an ethylene group is more preferable. Moreover, m in Chemical formula 5 is an integer of 1 to 3.
化１中のＹとしては、化２で示される有機基、化３で示される有機基、化４で示される有機基又は化５で示される有機基が挙げられるが、なかでも化２で示される有機基、化３で示される有機基又は化５で示される有機基が好ましく、化２で示される有機基又は化５で示される有機基がより好ましい。 Examples of Y in Chemical formula 1 include an organic group represented by Chemical formula 2, an organic group represented by Chemical formula 3, an organic group represented by Chemical formula 4 or an organic group represented by Chemical formula 5, among which An organic group represented by Chemical Formula 3 or an organic group represented by Chemical Formula 5 is preferred, and an organic group represented by Chemical Formula 2 or an organic group represented by Chemical Formula 5 is more preferred.
化１で示される芳香族化合物は、公知の方法により得ることができる。例えば、１）酸又はアルカリ触媒存在下で、メタノール、エタノール等の脂肪族アルコールに芳香族カルボン酸をエステル化する方法、２）アルカリ触媒存在下で、フェノール類にアルキレンオキシドを付加重合する方法等により得ることができる。また市販のものを使用することもできる。 The aromatic compound represented by Chemical Formula 1 can be obtained by a known method. For example, 1) a method in which an aromatic carboxylic acid is esterified with an aliphatic alcohol such as methanol or ethanol in the presence of an acid or an alkali catalyst, and 2) a method in which an alkylene oxide is added to a phenol in the presence of an alkali catalyst. Can be obtained. Commercially available products can also be used.
本発明の分散剤となるポリエステルに供するＢ成分は、化６で示される化合物及び化７で示される化合物から選ばれる一つ又は二つ以上である。 The component B to be provided to the polyester serving as the dispersant of the present invention is one or more selected from the compound represented by Chemical Formula 6 and the compound represented by Chemical Formula 7.
化６で示される化合物及び化７で示される化合物において、化６中及び化７中のＺ３〜Ｚ６は水素原子又は炭素数１〜１２のアルキル基である。これについては、Ｚ１について前記したことと同じである。 In the compound represented by Chemical formula 6 and the compound represented by Chemical formula 7, Z 3 to Z 6 in Chemical formula 6 and Chemical formula 7 are a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. This is the same as described above for Z 1 .
化７で示される化合物において、化７中のＲ４は炭素数１〜１６の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基である。かかる残基としては、１）メチレン基、エチレン基、トリメチレン基、メチルエチレン基、テトラメチレン基、エチルエチレン基、ペンタメチレン基、プロピルエチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基、ウンデカメチレン基、ドデカメチレン基、トリデカメチレン基、テトラデカメチレン基、ペンタデカメチレン基、ヘキサデカメチレン基等の炭素数１〜１６のアルキレン基、２）ビニレン基、プロペニレン基、ブテニレン基、ペンテニレン基、ヘキセニレン基、ヘプテニレン基、オクテニレン基、ノネニレン基、デセニレン基、ウンデセニレン基、ドデセニレン基、トリデセニレン基、テトラデセニレン基、ペンタデセニレン基、ヘキサデセニレン基等の炭素数２〜１６のアルケニレン基、３）エチニレン基、プロピニレン基、ブチニレン基、ペンチニレン基、ヘキシニレン基、ヘプチニレン基、オクチニレン基、ノニレン基、デシニレン基、ウンデシニレン基、ドデシニレン基、トリデシニレン基、テトラデシニレン基、ペンタデシニレン基、ヘキサデシニレン基等の炭素数２〜１６のアルキニレン基が挙げられる。なかでも炭素数１〜１２のアルキレン基が好ましい。 In the compound represented by Chemical formula 7, R 4 in Chemical formula 7 is a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 16 carbon atoms. Such residues include: 1) methylene group, ethylene group, trimethylene group, methylethylene group, tetramethylene group, ethylethylene group, pentamethylene group, propylethylene group, hexamethylene group, heptamethylene group, octamethylene group, nonamethylene Group, decamethylene group, undecamethylene group, dodecamethylene group, tridecamethylene group, tetradecamethylene group, pentadecamethylene group, hexadecamethylene group, etc., alkylene group having 1 to 16 carbon atoms, 2) vinylene group, propenylene Group, butenylene group, pentenylene group, hexenylene group, heptenylene group, octenylene group, nonenylene group, decenylene group, undecenylene group, dodecenylene group, tridecenylene group, tetradecenylene group, pentadecenylene group, hexadecenylene group, etc. Lukenylene, 3) ethynylene, propynylene, butynylene, pentynylene, hexynylene, heptynylene, octynylene, nonylene, decynylene, undecynylene, dodecynylene, tridecynylene, tetradecynylene, hexadecynylene, etc. And an alkynylene group having 2 to 16 carbon atoms. Of these, an alkylene group having 1 to 12 carbon atoms is preferable.
かかるＢ成分の化合物は、公知の方法により得ることができる。例えば、酸又はアルカリ触媒存在下で、適応する二価の脂肪酸に脂肪族アルコールをエステル化させることにより得ることができる。 Such B component compounds can be obtained by known methods. For example, it can be obtained by esterifying a suitable divalent fatty acid with an aliphatic alcohol in the presence of an acid or alkali catalyst.
本発明の分散剤となるポリエステルに供するＣ成分は、化８で示されるジオール化合物である。 The C component used for the polyester that is the dispersant of the present invention is a diol compound represented by Chemical Formula 8.
化８で示されるジオール化合物において、化８中のＲ５は炭素数１〜１８の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基である。かかる残基としては、１）メチレン基、エチレン基、トリメチレン基、メチルエチレン基、テトラメチレン基、エチルエチレン基、ペンタメチレン基、プロピルエチレン基、ヘキサメチレン基、ヘプタメチレン基、オクタメチレン基、ノナメチレン基、デカメチレン基、ウンデカメチレン基、ドデカメチレン基、トリデカメチレン基、テトラデカメチレン基、ペンタデカメチレン基、ヘキサデカメチレン基、オクタデカメチレン基等の炭素数１〜１８のアルキレン基、２）ビニレン基、プロペニレン基、ブテニレン基、ペンテニレン基、ヘキセニレン基、ヘプテニレン基、オクテニレン基、ノネニレン基、デセニレン基、ウンデセニレン基、ドデセニレン基、トリデセニレン基、テトラデセニレン基、ペンタデセニレン基、ヘキサデセニレン基、ヘプタデセニレン基、オクタデセニレン基等の炭素数２〜１８のアルケニレン基、３）エチニレン基、プロピニレン基、ブチニレン基、ペンチニレン基、ヘキシニレン基、ヘプチニレン基、オクチニレン基、ノニニレン基、デシニレン基、ウンデシニレン基、ドデシニレン基、トリデシニレン基、テトラデシニレン基、ペンタデシニレン基、ヘキサデシニレン基、ヘプタデシニレン基、オクタデシニレン基等の炭素数２〜１８のアルキニレン基が挙げられる。なかでも炭素数１〜１４のアルキレン基が好ましい。 In the diol compound represented by Chemical formula 8, R 5 in Chemical formula 8 is a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 18 carbon atoms. Such residues include: 1) methylene group, ethylene group, trimethylene group, methylethylene group, tetramethylene group, ethylethylene group, pentamethylene group, propylethylene group, hexamethylene group, heptamethylene group, octamethylene group, nonamethylene Group, decamethylene group, undecamethylene group, dodecamethylene group, tridecamethylene group, tetradecamethylene group, pentadecamethylene group, hexadecamethylene group, octadecamethylene group, etc., an alkylene group having 1 to 18 carbon atoms, 2 ) Vinylene group, propenylene group, butenylene group, pentenylene group, hexenylene group, heptenylene group, octenylene group, nonenylene group, decenylene group, undecenylene group, dodecenylene group, tridecenylene group, tetradecenylene group, pentadecenylene group, hexadecenylene group C 2-18 alkenylene group such as heptadecenylene group, octadecenylene group, etc. 3) Ethynylene group, propynylene group, butynylene group, pentynylene group, hexynylene group, heptynylene group, octynylene group, nonynylene group, decynylene group, undecynylene group, dodecynylene group And an alkynylene group having 2 to 18 carbon atoms such as a group, a tridecynylene group, a tetradecynylene group, a pentadecynylene group, a hexadecynylene group, a heptadecynylene group, and an octadecynylene group. Of these, an alkylene group having 1 to 14 carbon atoms is preferable.
かかるＣ成分のジオール化合物は、公知の方法により得ることができ、また市販のものを使用することもできる。 Such a diol compound of component C can be obtained by a known method, or a commercially available product can also be used.
本発明の分散剤となるポリエステルは、以上説明したようなＡ成分、Ｂ成分及びＣ成分を重縮合したものであるが、なかでも、全構成単位中に、Ａ成分から形成された構成単位を１〜２０モル％の範囲内で有するものが好ましく、更にＢ成分から形成された構成単位及びＣ成分から形成された構成単位をそれぞれ３０〜６０モル％の範囲内で有するものがより好ましい。 The polyester used as the dispersant of the present invention is obtained by polycondensation of the A component, the B component and the C component as described above. Among them, the structural unit formed from the A component is included in all the structural units. What has in the range of 1-20 mol% is preferable, and what has further the structural unit formed from B component and the structural unit formed from C component in the range of 30-60 mol% is more preferable.
かかるポリエステルは、二塩基酸とジオールの直接重縮合法、二塩基酸ジエステルとジオールのエステル交換法等の公知の方法により得ることができる。例えば、二塩基酸又は二塩基酸ジエステルとジオールを所定の割合で混合して混合物となし、触媒の存在下、１５０〜３００℃の温度条件下で混合物を反応させて合成する。通常は、反応性を高めるために二塩基酸又は二塩基酸ジエステルに対してジオールを過剰に用いて、常圧下でのエステル化反応あるいはエステル交換反応によりグリコール末端の低縮合体を合成する工程（以下第１工程という）と、これをさらに１００００Ｐａ以下の高真空下でエステル交換による重縮合反応（脱グリコール反応）により任意の高分子量のポリエステルを合成する工程（以下第２工程という）の２段階の工程により合成される。ここで過剰に用いるジオールとしては、第２工程の脱グリコールを容易にしたり、分子量や酸価を管理しやすくするために、エチレングリコールが好ましい。触媒としては、通常ポリエステルの重縮合に使用されているものがそのまま使用できるが、エステル化あるいはエステル交換反応（第１工程）の触媒としては、アルカリ金属、アルカリ土類金属、亜鉛、コバルト、マンガン、カドミニウム、鉛、スズ、チタン、ジルコニウム等の酸化物、炭酸塩、酢酸塩及びアルコラート等が挙げられ、また重縮合反応（第２工程）の触媒としては、アンチモン、鉄、鉛、スズ、ゲルマニウム、チタン、マンガン、コバルト、亜鉛等の化合物が挙げられる。分子量、融点、酸価等のポリエステルの物性は第２工程の反応の温度、圧力、触媒の種類や量及び反応時間により適宜調節する。 Such a polyester can be obtained by a known method such as a direct polycondensation method of a dibasic acid and a diol, or a transesterification method of a dibasic acid diester and a diol. For example, a dibasic acid or dibasic acid diester and a diol are mixed in a predetermined ratio to form a mixture, and the mixture is reacted in the presence of a catalyst at a temperature of 150 to 300 ° C. for synthesis. Usually, in order to enhance the reactivity, a diol is excessively used with respect to a dibasic acid or a dibasic acid diester, and a glycol-terminated low-condensate is synthesized by esterification or transesterification under normal pressure ( The following two steps: a first step) and a step of synthesizing an arbitrary high molecular weight polyester by a polycondensation reaction (deglycolization reaction) by transesterification under a high vacuum of 10,000 Pa or less (hereinafter referred to as a second step). The process is synthesized. As the diol used excessively, ethylene glycol is preferable in order to facilitate the deglycolization in the second step and to easily manage the molecular weight and the acid value. As the catalyst, those usually used for polyester polycondensation can be used as they are, but as catalysts for esterification or transesterification (first step), alkali metals, alkaline earth metals, zinc, cobalt, manganese , Cadmium, lead, tin, titanium, zirconium and other oxides, carbonates, acetates and alcoholates, etc., and polycondensation (second step) catalysts include antimony, iron, lead, tin, germanium , Compounds such as titanium, manganese, cobalt, and zinc. The physical properties of the polyester, such as molecular weight, melting point, acid value, etc. are appropriately adjusted depending on the temperature, pressure, type and amount of the catalyst and reaction time in the second step.
かかるポリエステルの重縮合に当たっては、質量平均分子量が１０００〜１０００００の範囲内、融点が２０〜１２０℃の範囲内及び酸価が１０mgＫＯＨ／ｇ以下になるように調整することが好ましい。特に好ましくは、質量平均分子量が２０００〜２００００の範囲内、融点が４０〜１００℃の範囲内及び酸価が２．０mgＫＯＨ／ｇ以下になるように調整する。 In the polycondensation of such a polyester, it is preferable to adjust so that the mass average molecular weight is in the range of 1,000 to 100,000, the melting point is in the range of 20 to 120 ° C., and the acid value is 10 mgKOH / g or less. Particularly preferably, the mass average molecular weight is adjusted in the range of 2000 to 20000, the melting point is in the range of 40 to 100 ° C., and the acid value is adjusted to 2.0 mgKOH / g or less.
次に、本発明に係る顔料組成物（以下、単に本発明の顔料組成物という）について説明する。本発明の顔料組成物は、顔料、非水系溶媒、バインダー樹脂及び本発明の分散剤を含有してなるものである。 Next, the pigment composition according to the present invention (hereinafter simply referred to as the pigment composition of the present invention) will be described. The pigment composition of the present invention comprises a pigment, a non-aqueous solvent, a binder resin, and the dispersant of the present invention.
本発明の顔料組成物に供する顔料としては、１）アゾ系、ジアゾ系、縮合アゾ系、アントラキノン系、アントラピリジン系、イソインドリノン系、イソインドリン系、インダンスロン系、キナクリドン系、ジオキサン系、ジオキサジン系、ジケトピロロピロール系、チオインジゴ系、ピランスロン系、フタロシアニン系、フラバントロン系、ベンゾイミダゾロン系、ペリレン系等の有機顔料、２）鉄、クロム、チタン、ニッケル、亜鉛、バナジウム、コバルト等の金属の酸化物、３）カドミウム、亜鉛、バリウム等の金属の硫化物、及び４）炭酸カルシウム、炭酸バリウム、紺青、群青、カーボンブラック、タルク、クレー等の無機顔料が挙げられる。なかでも有機顔料が好ましい。 Examples of the pigment to be used in the pigment composition of the present invention include 1) azo, diazo, condensed azo, anthraquinone, anthrapyridine, isoindolinone, isoindoline, indanthrone, quinacridone, and dioxane. , Dioxazine, diketopyrrolopyrrole, thioindigo, pyranthrone, phthalocyanine, flavantron, benzimidazolone, perylene, etc. 2) iron, chromium, titanium, nickel, zinc, vanadium, cobalt And oxides of metals such as 3) sulfides of metals such as cadmium, zinc and barium, and 4) inorganic pigments such as calcium carbonate, barium carbonate, bitumen, ultramarine, carbon black, talc and clay. Of these, organic pigments are preferred.
本発明の顔料組成物に供する非水系溶媒としては、各種の炭化水素化合物、各種のアルコール類、各種のエーテル化合物、各種のケトン化合物、各種のエステル化合物及び各種のアミド化合物等が挙げられる。 Examples of the non-aqueous solvent used in the pigment composition of the present invention include various hydrocarbon compounds, various alcohols, various ether compounds, various ketone compounds, various ester compounds, and various amide compounds.
本発明の顔料組成物に供するバインダー樹脂としては、天然ゴム、合成ゴム、アクリル樹脂、アルキド樹脂、エポキシ樹脂、ポリエステル樹脂、ポリウレタン樹脂、ブタジエン樹脂、メラミン樹脂、シリコーン樹脂、ポリ塩化ビニル樹脂、ポリ塩化ビニリデン樹脂、ポリ酢酸ビニル樹脂、ポリスチレン樹脂及びフッ素樹脂などが挙げられる。かかるバインダー樹脂は通常、顔料１００質量部に対して１０〜２００質量部の割合で用いる。 The binder resin used in the pigment composition of the present invention includes natural rubber, synthetic rubber, acrylic resin, alkyd resin, epoxy resin, polyester resin, polyurethane resin, butadiene resin, melamine resin, silicone resin, polyvinyl chloride resin, polyvinyl chloride. Examples include vinylidene resin, polyvinyl acetate resin, polystyrene resin, and fluororesin. Such a binder resin is usually used at a ratio of 10 to 200 parts by mass with respect to 100 parts by mass of the pigment.
本発明の顔料組成物は、顔料、非水系溶媒、バインダー樹脂及び本発明の分散剤を含有してなるものであるが、顔料１００質量部に対し、本発明の分散剤を５〜４０質量部の割合で含有させることが好ましい。 The pigment composition of the present invention comprises a pigment, a non-aqueous solvent, a binder resin, and the dispersant of the present invention. The dispersant of the present invention is 5 to 40 parts by mass with respect to 100 parts by mass of the pigment. It is preferable to make it contain in the ratio.
本発明の顔料組成物を使用するに際しては、本発明に係る顔料組成物と共に他の成分、例えば可塑剤、消泡剤、沈降防止剤、増粘剤やレベリング剤やダレ止め剤等の粘性調整剤、濡れ剤、皮張り防止剤、酸化防止剤、紫外線吸収剤、帯電防止剤、防錆剤、防腐剤、難燃剤、粘着付与剤、本発明以外の分散剤等を、本発明の効果を損わない範囲で併用することができる。 When using the pigment composition of the present invention, other components such as plasticizers, antifoaming agents, anti-settling agents, thickeners, leveling agents and anti-sagging agents are used together with the pigment composition according to the present invention. Agents, wetting agents, anti-skinning agents, antioxidants, UV absorbers, antistatic agents, rust inhibitors, preservatives, flame retardants, tackifiers, dispersants other than the present invention, and the like. They can be used in combination as long as they are not damaged.
本発明の顔料組成物を製造するために使用する分散機としては、サンドミル、ビーズミル、ボールミル、ロールミル、マイクロフルイタイザー、ホモミキサー、ペイントシェーカー、アトライタなどが挙げられる。 Examples of the disperser used for producing the pigment composition of the present invention include a sand mill, a bead mill, a ball mill, a roll mill, a microfluidizer, a homomixer, a paint shaker, and an attritor.
以上説明した本発明には、良好な分散性を示し、またそれが安定維持され、更に得られる塗膜が色調の再現性に優れるという効果がある。 The present invention described above has the effect that it exhibits good dispersibility, is stably maintained, and the resulting coating film is excellent in color tone reproducibility.
以下、本発明の構成及び効果をより具体的にするため、実施例及び比較例を挙げるが、本発明がこれらの実施例に限定されるというものではない。尚、以下の実施例及び比較例において、部は質量部を、また％は質量％を意味する。 Hereinafter, in order to make the configuration and effects of the present invention more specific, examples and comparative examples will be described. However, the present invention is not limited to these examples. In the following Examples and Comparative Examples, “part” means “part by mass” and “%” means “% by mass”.
試験区分１（Ａ成分等の合成）
・化１で示される芳香族化合物（Ａ−２）の合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、９−アントラセンカルボン酸４４．４ｇ（０．２モル）及びメタノール４００mlを仕込み、さらに触媒として濃硫酸１ｇを添加してから加熱し、温度を約６４℃に保ち、１０時間加熱還流させてエステル化反応を行った。反応終了後、メタノールを減圧して留去し、残渣をジエチルエーテル中に溶解した。ジエチルエーテル溶液を希炭酸ナトリウム水溶液を使用して抽出洗浄した後、水で洗浄した。ジエチルエーテルを減圧留去して芳香族化合物（Ａ−２）を得た。
Test category 1 (synthesis of component A etc.)
Synthesis of aromatic compound (A-2) represented by Chemical Formula 1 In a four-necked flask equipped with a stirrer, thermometer, and condenser, 44.4 g (0.2 mol) of 9-anthracenecarboxylic acid and 400 ml of methanol were added. Then, 1 g of concentrated sulfuric acid was added as a catalyst, followed by heating. The temperature was maintained at about 64 ° C., and the mixture was heated to reflux for 10 hours to carry out an esterification reaction. After completion of the reaction, methanol was distilled off under reduced pressure, and the residue was dissolved in diethyl ether. The diethyl ether solution was extracted and washed using a dilute aqueous sodium carbonate solution, and then washed with water. Diethyl ether was distilled off under reduced pressure to obtain an aromatic compound (A-2).
・化１で示される芳香族化合物（Ａ−３）の合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、９−アントラセンカルボン酸４４．４ｇ（０．２モル）、ｎ−ブタノール２２．２ｇ（０．３モル）及びキシレン４００mlを仕込み、さらに触媒としてｐ−トルエンスルホン酸一水和物０．７ｇを添加してから加熱し、窒素ガスを導入しながら温度を１３８〜１４４℃の範囲に保ち、８時間加熱還流させ、生成する水をディーンスターク管にて系外に除去してエステル化反応を行った。反応終了後、希炭酸ナトリウム水溶液にて抽出洗浄した後、水で洗浄した。キシレンと過剰のｎ−ブタノールを減圧留去して芳香族化合物（Ａ−３）を得た。
Synthesis of aromatic compound (A-3) represented by Chemical Formula 1 In a four-necked flask equipped with a stirrer, a thermometer and a condenser, 44.4 g (0.2 mol) of 9-anthracenecarboxylic acid, n-butanol 22.2 g (0.3 mol) and 400 ml of xylene were charged, and 0.7 g of p-toluenesulfonic acid monohydrate was added as a catalyst, followed by heating and the temperature being 138 to 144 ° C. while introducing nitrogen gas. Within the above range, the mixture was heated to reflux for 8 hours, and the produced water was removed from the system with a Dean-Stark tube to carry out an esterification reaction. After completion of the reaction, the mixture was extracted and washed with a dilute aqueous sodium carbonate solution, and then washed with water. Xylene and excess n-butanol were distilled off under reduced pressure to obtain an aromatic compound (A-3).
・化１で示される芳香族化合物（Ａ−４）及び比較のための化合物（ａ−１）の合成
芳香族化合物（Ａ−３）と同様にして、表１に記載の芳香族化合物（Ａ−４）及び（ａ−１）を合成した。
Synthesis of aromatic compound (A-4) represented by Chemical Formula 1 and compound (a-1) for comparison In the same manner as the aromatic compound (A-3), the aromatic compound (A -4) and (a-1) were synthesized.
・化１で示される芳香族化合物（Ａ−６）の合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、アントラセン８０．２ｇ（０．４５モル）、モノクロル酢酸１４１．８ｇ（１．５０モル）、酸化第二鉄８７．６ｇ及び臭化カリウム０．４ｇを仕込み、１９０〜２３０℃にて２４時間反応させた。反応物を熱カセイソーダ水溶液で抽出し、塩酸で酸性にして析出物をろ過することにより得た。少量の塩酸を加えた熱水を用い、再結晶してアントラセン酢酸を得た。得られたアントラセン酢酸を用い、芳香族化合物（Ａ−２）と同様にして、芳香族化合物（Ａ−６）を得た。
Synthesis of aromatic compound (A-6) represented by Chemical Formula 1 In a four-necked flask equipped with a stirrer, thermometer and condenser, anthracene 80.2 g (0.45 mol), monochloroacetic acid 141.8 g (1 .50 mol), 87.6 g of ferric oxide and 0.4 g of potassium bromide were charged and reacted at 190 to 230 ° C. for 24 hours. The reaction product was extracted with a hot caustic soda aqueous solution, acidified with hydrochloric acid, and the precipitate was filtered. Recrystallization was performed using hot water to which a small amount of hydrochloric acid was added to obtain anthracene acetic acid. Using the obtained anthracene acetic acid, the aromatic compound (A-6) was obtained in the same manner as the aromatic compound (A-2).
・化１で示される芳香族化合物（Ａ−７）、（Ａ−８）及び比較のための化合物（ａ−３）の合成
芳香族化合物（Ａ−６）と同様にして、表１に記載の芳香族化合物（Ａ−７）、（Ａ−８）及び（ａ−３）を得た。
Synthesis of aromatic compounds (A-7) and (A-8) represented by Chemical Formula 1 and compound (a-3) for comparison As shown in Table 1, in the same manner as the aromatic compound (A-6) Aromatic compounds (A-7), (A-8) and (a-3) were obtained.
・化１で示される芳香族化合物（Ａ−１２）の合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、水素化リチウムアルミニウム３．４ｇ（０．０８６モル）及びジエチルエーテル８０mlを仕込み、撹拌下、１１−フェニルウンデカン酸（芳香族化合物（Ａ−８）の合成において中間物として得られたもの）２６．２ｇ（０．１０モル）をジエチルエーテル８０mlに溶解した溶液を滴下した後、１時間加熱還流させた。反応液を氷浴で冷却し、１０％炭酸水素ナトリウム水溶液１０ｇを加え、さらに２０％水酸化ナトリウム水溶液２０ｇを加えた。有機層を採取して水洗後、硫酸ナトリウムで乾燥させてから、ジエチルエーテルを留去して、芳香族化合物（Ａ−１２）を得た。
Synthesis of aromatic compound (A-12) represented by Chemical Formula 1 In a four-necked flask equipped with a stirrer, thermometer and condenser, 3.4 g (0.086 mol) of lithium aluminum hydride and 80 ml of diethyl ether were added. A solution prepared by dissolving 26.2 g (0.10 mol) of 11-phenylundecanoic acid (obtained as an intermediate in the synthesis of aromatic compound (A-8)) in 80 ml of diethyl ether was added dropwise with stirring and stirring. Thereafter, the mixture was heated to reflux for 1 hour. The reaction solution was cooled in an ice bath, 10 g of 10% aqueous sodium hydrogen carbonate solution was added, and 20 g of 20% aqueous sodium hydroxide solution was further added. The organic layer was collected, washed with water and dried over sodium sulfate, and then diethyl ether was distilled off to obtain an aromatic compound (A-12).
・比較のための化合物（ａ−４）の合成
芳香族化合物（Ａ−１２）と同様にして、表１に記載の化合物（ａ−４）を得た。
-Synthesis | combination of the compound (a-4) for a comparison The compound (a-4) of Table 1 was obtained like the aromatic compound (A-12).
・化１で示される芳香族化合物（Ａ−１３）の合成
撹拌機、温度計を備えたＳＵＳ製オートクレーブに、２−ナフトール１４４．２ｇ（１．０モル）及び水酸化カリウム０．２ｇを仕込み、系内を窒素置換した後、１４０〜１５０℃にてエチレンオキシド８８．１ｇ（２．０モル）を導入した。その後、１時間同温度で熟成を行った。冷却後、反応物を四つ口フラスコに移し、吸着剤（協和化学工業社のキョーワード６００Ｓ）１．１ｇを添加して、１００〜１２０℃にて１時間脱水を行い、ろ過して芳香族化合物（Ａ−１３）を得た。
Synthesis of aromatic compound (A-13) represented by Chemical Formula 1 A SUS autoclave equipped with a stirrer and a thermometer was charged with 144.2 g (1.0 mol) of 2-naphthol and 0.2 g of potassium hydroxide. After replacing the system with nitrogen, 88.1 g (2.0 mol) of ethylene oxide was introduced at 140 to 150 ° C. Thereafter, aging was carried out at the same temperature for 1 hour. After cooling, the reaction product is transferred to a four-necked flask, 1.1 g of an adsorbent (KYOWARD 600S, Kyowa Chemical Industry Co., Ltd.) is added, dehydrated at 100 to 120 ° C. for 1 hour, filtered and aromatic. Compound (A-13) was obtained.
・化１で示される芳香族化合物（Ａ−１４）〜（Ａ−１６）の合成
芳香族化合物（Ａ−１３）と同様にして、表１に記載の芳香族化合物（Ａ−１４）〜（Ａ−１６）を得た。
Synthesis of aromatic compounds (A-14) to (A-16) represented by Chemical formula 1 In the same manner as the aromatic compounds (A-13), the aromatic compounds (A-14) to (A-14) to ( A-16) was obtained.
本発明で使用したＡ成分としての芳香族化合物を表１〜４に示した。なお、（Ａ−１）、（Ａ−５）、（Ａ−９）〜（Ａ−１１）及び比較のための化合物（ａ−２）は市販品を使用した。
The aromatic compounds as the component A used in the present invention are shown in Tables 1 to 4. Commercially available products were used as (A-1), (A-5), (A-9) to (A-11) and the compound (a-2) for comparison.
試験区分２（Ｂ成分等の合成）
・化６で示される化合物（Ｂ−４）の合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、シュウ酸１８．０ｇ（０．２モル）、１−オクタノール６５．１ｇ（０．５モル）及びキシレン４００mlを仕込み、さらに触媒としてｐ−トルエンスルホン酸一水和物０．７ｇを添加して、窒素ガスを導入しながら８時間加熱還流させ、生成する水をディーンスターク管にて系外に除去してエステル化反応を行った。反応終了後、希炭酸ナトリウム水溶液にて抽出洗浄した後、水で洗浄した。キシレンと過剰の１−オクタノールを減圧留去してエステル化合物（Ｂ−４）を得た。
Test category 2 (synthesis of component B)
Synthesis of compound (B-4) represented by Chemical formula 6 In a four-necked flask equipped with a stirrer, a thermometer and a condenser, 18.0 g (0.2 mol) of oxalic acid, 65.1 g of 1-octanol (0 0.5 mol) and 400 ml of xylene, 0.7 g of p-toluenesulfonic acid monohydrate was added as a catalyst, and the mixture was heated to reflux for 8 hours while introducing nitrogen gas, and the resulting water was put into a Dean-Stark tube. Then, it was removed out of the system and an esterification reaction was carried out. After completion of the reaction, the mixture was extracted and washed with a dilute aqueous sodium carbonate solution, and then washed with water. Xylene and excess 1-octanol were distilled off under reduced pressure to obtain an ester compound (B-4).
・比較のためのエステル化合物（ｂ−１）の合成
エステル化合物（Ｂ−４）と同様にして、表５に記載のエステル化合物（ｂ−１）を得た。
-Synthesis | combination of the ester compound (b-1) for a comparison The ester compound (b-1) of Table 5 was obtained like the ester compound (B-4).
・化７で示される化合物（Ｂ−１０）の合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、ヘキサデカン二酸５７．３ｇ（０．２モル）、ｎ−ブタノール３７．１ｇ（０．５モル）及びキシレン４００mlを仕込み、さらに触媒としてｐ−トルエンスルホン酸一水和物０．７ｇを添加して、窒素ガスを導入しながら８時間加熱還流させ、生成する水をディーンスターク管にて系外に除去してエステル化反応を行った。反応終了後、希炭酸ナトリウム水溶液にて抽出洗浄した後、水で洗浄した。キシレンと過剰のｎ−ブタノールを減圧留去してエステル化合物（Ｂ−１０）を得た。
-Synthesis | combination of the compound (B-10) shown by Chemical formula 7 In a four-necked flask equipped with a stirrer, a thermometer, and a condenser, 57.3 g (0.2 mol) of hexadecanedioic acid and 37.1 g of n-butanol ( 0.5 mol) and 400 ml of xylene, 0.7 g of p-toluenesulfonic acid monohydrate was added as a catalyst, and the mixture was heated to reflux for 8 hours while introducing nitrogen gas. And then the esterification reaction was carried out. After completion of the reaction, the mixture was extracted and washed with a dilute aqueous sodium carbonate solution, and then washed with water. Xylene and excess n-butanol were distilled off under reduced pressure to obtain an ester compound (B-10).
・比較のためのエステル化合物（ｂ−２）の合成
エステル化合物（Ｂ−１０）と同様にして、表６に記載のエステル化合物（ｂ−２）を得た。
-Synthesis | combination of ester compound (b-2) for comparison The ester compound (b-2) of Table 6 was obtained like the ester compound (B-10).
本発明で使用したＢ成分としてのジカルボン酸化合物又はジカルボン酸化合物と脂肪族アルコールとのエステル化合物を表５及び表６に示した。なお、（Ｂ−１）〜（Ｂ−３）、（Ｂ−５）〜（Ｂ−９）は市販品を使用した。 Table 5 and Table 6 show the dicarboxylic acid compound or the ester compound of the dicarboxylic acid compound and the aliphatic alcohol as the component B used in the present invention. In addition, (B-1)-(B-3) and (B-5)-(B-9) used the commercial item.
試験区分３（Ｃ成分等の内容）
本発明で使用したＣ成分としての市販のジオール化合物を表７に示した。
Test category 3 (contents of component C, etc.)
Table 7 shows commercially available diol compounds as the component C used in the present invention.
試験区分４（分散剤としてのポリエステルの合成）
・実施例１：分散剤（Ｐ−１）としてのポリエステルの合成
撹拌機、温度計、コンデンサーを備えた四つ口フラスコに、芳香族化合物（Ａ−１）３４．４ｇ（０．２０モル）と、ジカルボン酸（Ｂ−８）１４１．６ｇ（０．７０モル）及びジオール化合物（Ｃ−３）９４．５ｇ（０．８０モル）を投入し、さらに過剰のジオール成分としてエチレングリコール１２．４ｇ（０．２０モル）を加えてから、窒素気流下、撹拌しながら１１０℃まで加熱した。触媒としてテトラブトキシチタネートを０．０８ｇ加えてからさらに加熱し、生成する水を系外に留去しながら２２０℃で２時間エステル化した。さらに温度を２２０℃に保ちながら５０００Ｐａ以下で、エチレングリコールを留去しながら２時間重縮合を継続した。反応終了後、温度が１００℃になるまで冷却した。冷却後撹拌を止め、反応物を取り出し、ポリエステルを得た。これを分散剤（Ｐ−１）とした。
Test Category 4 (Synthesis of polyester as a dispersant)
Example 1 Synthesis of Polyester as Dispersant (P-1) In a four-necked flask equipped with a stirrer, a thermometer and a condenser, 34.4 g (0.20 mol) of the aromatic compound (A-1) And 141.6 g (0.70 mol) of dicarboxylic acid (B-8) and 94.5 g (0.80 mol) of diol compound (C-3) were added, and 12.4 g of ethylene glycol as an excess diol component. (0.20 mol) was added and heated to 110 ° C. with stirring under a nitrogen stream. After adding 0.08 g of tetrabutoxy titanate as a catalyst, the mixture was further heated, and esterified at 220 ° C. for 2 hours while distilling off the generated water to the outside of the system. Furthermore, polycondensation was continued for 2 hours while distilling off ethylene glycol at 5000 Pa or less while maintaining the temperature at 220 ° C. After completion of the reaction, it was cooled until the temperature reached 100 ° C. After cooling, stirring was stopped and the reaction product was taken out to obtain a polyester. This was designated as Dispersant (P-1).
・実施例２〜２３及び比較例１〜４：分散剤（Ｐ−２）〜（Ｐ−２３）及び（ｐ−１）〜（ｐ−４）としてのポリエステルの合成
分散剤（Ｐ−１）と同様にして、分散剤（Ｐ−２）〜（Ｐ−２３）及び比較のための分散剤（ｐ−１）〜（ｐ−４）を得た。これらの内容を表８にまとめて示した。ここで、分散剤（Ｐ−２２）を除き、過剰のジオール成分としては、カルボキシル基と水酸基の当量比が１：１．２となるようにエチレングリコールを用いた。分散剤Ｐ−２２は、過剰のジオール成分としてのエチレングリコール及び触媒としてのテトラブトキシチタネートを添加せずに、反応を行った。また分散剤（Ｐ−２３）は、エステル化後に過剰のジオール成分としてのエチレングリコールを留去せずに重縮合を行なった。したがってこの場合の表８記載のＣ成分のモル比は過剰のジオール成分としてのエチレングリコールを含んだ値である。
Examples 2 to 23 and Comparative Examples 1 to 4: Synthesis of polyesters as dispersants (P-2) to (P-23) and (p-1) to (p-4) Dispersant (P-1) In the same manner, dispersants (P-2) to (P-23) and comparative dispersants (p-1) to (p-4) were obtained. These contents are summarized in Table 8. Here, with the exception of the dispersant (P-22), as the excess diol component, ethylene glycol was used so that the equivalent ratio of carboxyl group to hydroxyl group was 1: 1.2. Dispersant P-22 reacted without adding ethylene glycol as an excess diol component and tetrabutoxy titanate as a catalyst. The dispersant (P-23) was subjected to polycondensation without distilling off ethylene glycol as an excess diol component after esterification. Therefore, in this case, the molar ratio of component C described in Table 8 is a value including ethylene glycol as an excess diol component.
表８において、
質量平均分子量：テトラヒドロフランを溶媒とし、既知分子量のポリスチレンを標準としてＧＰＣ法で求めた。
融点：サンプル５mgをアルミニウム製サンプルパンに採取し、ＤＳＣを用いて昇温速度１０℃/分の条件で測定し、ピーク温度を求め、融点とした。
酸価：サンプル５ｇをキシレン３０ml及びメタノール３０mlの混合溶媒に溶解し、０．１Ｎ水酸化カリウムメタノール溶液を滴定液として、電位差自動滴定装置を用いて測定した。
In Table 8,
Mass average molecular weight: It was determined by GPC using tetrahydrofuran as a solvent and polystyrene having a known molecular weight as a standard.
Melting point: 5 mg of a sample was taken in an aluminum sample pan, measured using DSC at a temperature increase rate of 10 ° C./min, the peak temperature was determined, and the melting point was obtained.
Acid value: 5 g of a sample was dissolved in a mixed solvent of 30 ml of xylene and 30 ml of methanol, and a 0.1N potassium hydroxide methanol solution was used as a titrant and measured using a potentiometric automatic titrator.
試験区分５（顔料組成物の調製）
・実施例２４
分散剤（Ｐ−１）０．６５ｇ、顔料（Ｑ−１）６．４５ｇ、バインダー樹脂（Ｒ−１）６．４５ｇ、キシレン（Ｓ−２）３６．４５ｇ及び直径２mmのジルコニアビーズ１００ｇを１００mlのバイアル瓶に入れ、ペイントシェーカー（東洋精機製作所社製）で５時間分散処理をして、実施例２４の顔料組成物を得た。
Test Category 5 (Preparation of pigment composition)
Example 24
100 ml of 0.65 g of dispersant (P-1), 6.45 g of pigment (Q-1), 6.45 g of binder resin (R-1), 36.45 g of xylene (S-2) and 100 g of zirconia beads having a diameter of 2 mm The pigment composition of Example 24 was obtained by dispersing in a paint shaker (manufactured by Toyo Seiki Seisakusho) for 5 hours.
・実施例２５〜４６及び比較例５〜８
実施例２４の顔料組成物と同様にして、実施例２５〜４６及び比較例５〜８の顔料組成物を調製した。これらの内容を表９にまとめて示した。
-Examples 25-46 and Comparative Examples 5-8
The pigment compositions of Examples 25 to 46 and Comparative Examples 5 to 8 were prepared in the same manner as the pigment composition of Example 24. These contents are summarized in Table 9.
試験区分６（顔料組成物の評価）
試験区分３で調製した顔料組成物について、分散性、その安定性、塗膜の色再現性の指標として、外観、粘度、粒径及び塗膜の光沢を、初期及び経時後において次のように評価した。結果を表９にまとめて示した。
Test category 6 (evaluation of pigment composition)
For the pigment composition prepared in Test Category 3, as an indicator of dispersibility, stability, and color reproducibility of the coating film, the appearance, viscosity, particle size, and gloss of the coating film are as follows at the initial stage and after the lapse of time. evaluated. The results are summarized in Table 9.
・粒径
試験区分５で調製した顔料組成物を、その調製に使用したバインダー樹脂と溶媒との混合液（混合比率は各々の顔料組成物の調製時と同じ）で１０倍に希釈して測定用試料とし、粒度分布計（大塚電子社製の商品名ＦＰＡＲ−１０００）を用い、平均粒径を測定して次の基準で評価した。
◎：平均粒径が２００ｎｍ未満である
○：平均粒径が２００ｎｍ以上３００ｎｍ未満である
△：平均粒径が３００ｎｍ以上４００ｎｍ未満である
×：平均粒径が４００ｎｍ以上である
・ Particle size The pigment composition prepared in Test Category 5 was diluted 10 times with the mixed solution of binder resin and solvent used in the preparation (mixing ratio is the same as when preparing each pigment composition). Using a particle size distribution meter (trade name FPAR-1000, manufactured by Otsuka Electronics Co., Ltd.), the average particle size was measured and evaluated according to the following criteria.
A: Average particle diameter is less than 200 nm B: Average particle diameter is 200 nm or more and less than 300 nm Δ: Average particle diameter is 300 nm or more and less than 400 nm X: Average particle diameter is 400 nm or more
・光沢
試験区分５で調製した顔料組成物を、マイヤーバー（Ｎｏ．１２）を用い、厚み０．０５mmのＰＥＴフィルム上に乾燥後の膜厚が０．０１mmとなるように塗布し、１００℃で２分間乾燥後、室温下で冷却して塗膜を形成し、光沢度を測定して次の基準で評価した。
◎：２０°グロスが８０以上である
○：２０°グロスが７０以上８０未満である
△：２０°グロスが６０以上７０未満である
×：２０°グロスが６０未満である
Gloss The pigment composition prepared in Test Category 5 was applied onto a PET film having a thickness of 0.05 mm using a Meyer bar (No. 12) so that the film thickness after drying would be 0.01 mm. After drying for 2 minutes, it was cooled at room temperature to form a coating film, and the glossiness was measured and evaluated according to the following criteria.
◎: 20 ° gloss is 80 or more ○: 20 ° gloss is 70 or more and less than 80 Δ: 20 ° gloss is 60 or more and less than 70 ×: 20 ° gloss is less than 60
・安定性１（粒径）
試験区分５で調製した顔料組成物を４０℃で１週間保存した後に、前記と同様にして粒径を測定し、その変化の割合により次の基準で評価した。
◎：初期値との変化率が５％未満である
○：初期値との変化率が５％以上１０％未満である
△：初期値との変化率が１０％以上１５％未満である
×：初期値との変化率が１５％以上である
・ Stability 1 (particle size)
After the pigment composition prepared in Test Category 5 was stored at 40 ° C. for 1 week, the particle size was measured in the same manner as described above, and evaluated according to the following criteria based on the rate of change.
A: Change rate from initial value is less than 5% B: Change rate from initial value is from 5% to less than 10% Δ: Change rate from initial value is from 10% to less than 15% ×: The rate of change from the initial value is 15% or more
・安定性２（光沢）
試験区分５で調製した顔料組成物を４０℃で１週間保存した後に、前記と同様にして塗膜を形成し、光沢度を測定して、その変化の割合により次の基準で評価した。
◎：初期値との変化率が５％未満である
○：初期値との変化率が５％以上１０％未満である
△：初期値との変化率が１０％以上１５％未満である
×：初期値との変化率が１５％以上である
・ Stability 2 (Glossy)
After the pigment composition prepared in Test Category 5 was stored at 40 ° C. for 1 week, a coating film was formed in the same manner as described above, the glossiness was measured, and the change was evaluated according to the following criteria.
A: Change rate from initial value is less than 5% B: Change rate from initial value is from 5% to less than 10% Δ: Change rate from initial value is from 10% to less than 15% ×: The rate of change from the initial value is 15% or more
・安定性３（外観）
試験区分５で調製した顔料組成物１０mlを０．１ml目盛りの共栓付きメスシリンダーに入れ、４０℃で１週間保存した後に、その外観を目視で観察し、次の基準で評価した。
◎：沈降量が０．１ml未満である。
○：沈降量が０．１ml以上０．２ml未満である。
△：沈降量が０．２ml以上０．３ml未満である。
×：沈降量が０．３ml以上である。
・ Stability 3 (Appearance)
10 ml of the pigment composition prepared in Test Category 5 was put in a measuring cylinder with a stopper of 0.1 ml and stored at 40 ° C. for 1 week. The appearance was visually observed and evaluated according to the following criteria.
A: The sedimentation amount is less than 0.1 ml.
○: The sedimentation amount is 0.1 ml or more and less than 0.2 ml.
Δ: The sedimentation amount is 0.2 ml or more and less than 0.3 ml.
X: The amount of sedimentation is 0.3 ml or more.
・安定性４（粘度）
試験区分５で調製した顔料組成物を４０℃で１週間保存した後に、Ｂ型粘度計（東機産業社）にて２５℃で６０ｒｐｍの条件下に粘度を測定し、次の基準で評価した。なお、ここで初期値とは４０℃保存前の顔料組成物を同条件で測定した値である。
◎：初期値との変化率が５％未満である
○：初期値との変化率が５％以上１０％未満である
△：初期値との変化率が１０％以上１５％未満である
×：初期値との変化率が１５％以上である
・ Stability 4 (viscosity)
After the pigment composition prepared in Test Category 5 was stored at 40 ° C. for 1 week, the viscosity was measured at 25 ° C. and 60 rpm with a B-type viscometer (Toki Sangyo Co., Ltd.) and evaluated according to the following criteria. . Here, the initial value is a value obtained by measuring the pigment composition before storage at 40 ° C. under the same conditions.
A: Change rate from initial value is less than 5% B: Change rate from initial value is from 5% to less than 10% Δ: Change rate from initial value is from 10% to less than 15% ×: The rate of change from the initial value is 15% or more
表９において、
顔料の部数：１００部
Ｐ−１〜Ｐ−２３，ｐ−１〜ｐ−４：表８に記載の分散剤
Ｑ−１：ＰＢ１５：３（東洋インキ製造社製の商品名ＬＩＯＮＯＬ ＢＬＵＥ ＦＧ−７３３０−ＰＡ）
Ｑ−２：ＰＹ７４（チバ・スペシャルティー・ケミカルズ社製の商品名ＩＲＧＡＬＩＴＥ ＹＥＬＬＯＷ ＧＯ）
Ｑ−３：ＰＲ１７７（チバ・スペシャルティー・ケミカルズ社製の商品名ＣＲＯＭＯＰＨＴＡＬ ＲＥＤ Ａ２Ｂ）
Ｒ−１：キシレンを４０％含有する常乾型アルキド樹脂（ＤＩＣ社製の商品名ベッコゾールＥＳ−４５０５−６０ｘ）
Ｒ−２：キシレンを４０％含有する焼付型アルキド樹脂（ＤＩＣ社製の商品名ベッコゾール１３０７−６０−ＥＬ）とキシレン、ブタノール及びメタノールを４０％含有するブチル化メラミン樹脂（ＤＩＣ社製の商品名スーパーベッカミンＪ−８２０−６０）を７０：３０の質量比で混合したもの
Ｒ−３：キシレン及びブタノールを４０％含有する焼付型アクリル樹脂（ＤＩＣ社製の商品名アクリディック５４−１７２−６０）と前記のスーパーベッカミンＪ−８２０−６０を７０：３０の質量比で混合したもの。
Ｒ−４：キシレン及び酢酸イソブチルを５０％含有するイソシアネート硬化型アクリル樹脂（ＤＩＣ社製の商品名アクリディックＡ−８２９）
Ｓ−１：シクロヘキサノン
Ｓ−２：キシレン
Ｓ−３：酢酸エチル
Ｓ−４：プロピレングリコールモノメチルエーテルアセテート
In Table 9,
Number of parts of pigment: 100 parts P-1 to P-23, p-1 to p-4: Dispersant described in Table 8 Q-1: PB15: 3 (trade name LIONOL BLUE FG-7330 manufactured by Toyo Ink Mfg. Co., Ltd.) -PA)
Q-2: PY74 (trade name IRGALITE YELLOW GO manufactured by Ciba Specialty Chemicals)
Q-3: PR177 (trade name CROMOPHTAL RED A2B manufactured by Ciba Specialty Chemicals)
R-1: A normally-dried alkyd resin containing 40% xylene (Beccosol ES-4505-60x, trade name by DIC)
R-2: Baking alkyd resin containing 40% xylene (trade name Beccosol 1307-60-EL manufactured by DIC) and butylated melamine resin containing 40% xylene, butanol and methanol (trade name manufactured by DIC) Super Beccamin J-820-60) mixed at a mass ratio of 70:30 R-3: Baking type acrylic resin containing 40% of xylene and butanol (trade name ACRYDIC 54-172-60 manufactured by DIC) ) And the above Super Becamine J-820-60 at a mass ratio of 70:30.
R-4: Isocyanate curable acrylic resin containing 50% of xylene and isobutyl acetate (trade name ACRYDIC A-829 manufactured by DIC)
S-1: Cyclohexanone S-2: Xylene S-3: Ethyl acetate S-4: Propylene glycol monomethyl ether acetate
Claims (14)
Ａ成分：下記の化１で示される芳香族化合物
Ｘ：アリール基
Ｙ：下記の化２で示される有機基、化３で示される有機基、化４で示される有機基又は化５で示される有機基
Ｚ１，Ｚ２：水素原子又は炭素数１〜１２のアルキル基
Ｒ１，Ｒ２：炭素数１〜１２の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
Ｒ３：炭素数２〜４の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
ｍ：１〜３の整数）］
Ｂ成分：下記の化６で示される化合物及び化７で示される化合物から選ばれる一つ又は二つ以上。
Ｒ ４ ：炭素数１〜１６の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基
Ｚ ３ ，Ｚ ４ ，Ｚ ５ ，Ｚ ６ ：水素原子又は炭素数１〜１２のアルキル基）
Ｃ成分：下記の化８で示されるジオール化合物。
Ｒ ５ ：炭素数１〜１８の脂肪族炭化水素化合物の両鎖端から各１個の水素原子を除いた残基） A non-aqueous pigment dispersant comprising a polyester obtained by polycondensation of the following components A, B and C:
Component A: aromatic compound represented by the following chemical formula 1
X: aryl group Y: organic group represented by the following chemical formula 2, organic group represented by chemical formula 3, organic group represented by chemical formula 4 or organic group represented by chemical formula 5
Z 1 , Z 2 : a hydrogen atom or an alkyl group having 1 to 12 carbon atoms R 1 , R 2 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 12 carbon atoms R 3 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 2 to 4 carbon atoms m: an integer of 1 to 3]]
Component B: One or more selected from the compound represented by the following chemical formula 6 and the compound represented by the chemical formula 7.
R 4 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 16 carbon atoms
Z 3 , Z 4 , Z 5 , Z 6 : a hydrogen atom or an alkyl group having 1 to 12 carbon atoms)
Component C: a diol compound represented by the following chemical formula 8.
R 5 : a residue obtained by removing one hydrogen atom from each chain end of an aliphatic hydrocarbon compound having 1 to 18 carbon atoms)
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