JP2011021155A - Triaryl methane-based and rhodamine-based pigment composition, and pigment dispersion using these - Google Patents
Triaryl methane-based and rhodamine-based pigment composition, and pigment dispersion using these Download PDFInfo
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- JP2011021155A JP2011021155A JP2009169327A JP2009169327A JP2011021155A JP 2011021155 A JP2011021155 A JP 2011021155A JP 2009169327 A JP2009169327 A JP 2009169327A JP 2009169327 A JP2009169327 A JP 2009169327A JP 2011021155 A JP2011021155 A JP 2011021155A
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- pigment
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- rhodamine
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- 239000000049 pigment Substances 0.000 title claims abstract description 107
- 239000006185 dispersion Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 title claims abstract description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- -1 substituted aryl sulfonic acid Chemical compound 0.000 abstract description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 0 *c1cc2ccccc2cc1 Chemical compound *c1cc2ccccc2cc1 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000001055 blue pigment Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229940110337 pigment blue 1 Drugs 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229940080299 sodium 2-naphthalenesulfonate Drugs 0.000 description 4
- YWPOLRBWRRKLMW-UHFFFAOYSA-M sodium;naphthalene-2-sulfonate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 YWPOLRBWRRKLMW-UHFFFAOYSA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000004922 lacquer 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
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFLOMAIEONDOLV-UHFFFAOYSA-N 2-oxalobenzoic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1C(O)=O LFLOMAIEONDOLV-UHFFFAOYSA-N 0.000 description 2
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 2
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-N 0.000 description 1
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- VHBSECWYEFJRNV-UHFFFAOYSA-N 2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.OC(=O)C1=CC=CC=C1O VHBSECWYEFJRNV-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VFMNIJOKAXPZLE-UHFFFAOYSA-N 4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC=C(S(O)(=O)=O)C=C1 VFMNIJOKAXPZLE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MZUSCVCCMHDHDF-UHFFFAOYSA-N P(=O)(=O)[W] Chemical compound P(=O)(=O)[W] MZUSCVCCMHDHDF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- LNIQEBQSPWOLPH-UHFFFAOYSA-N naphthalene-1-carboxylic acid Chemical compound OC(=O)c1cccc2ccccc12.OC(=O)c1cccc2ccccc12 LNIQEBQSPWOLPH-UHFFFAOYSA-N 0.000 description 1
- HKGOFWIZZIYCOS-UHFFFAOYSA-N naphthalene-2-sulfonic acid;hydrate Chemical compound O.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HKGOFWIZZIYCOS-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 description 1
- KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- BLXAGSNYHSQSRC-UHFFFAOYSA-M sodium;2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=CC=C1S([O-])(=O)=O BLXAGSNYHSQSRC-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/205—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene
- C09B35/21—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl- or triaryl- alkane or-alkene of diarylmethane or triarylmethane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
Abstract
Description
本発明は、トリアリールメタン系及びローダミン系顔料組成物に関し、より詳細には、耐光性及び耐熱性に優れたトリアリールメタン系及びローダミン系顔料組成物並びにこれらを用いた顔料分散体に関する。 The present invention relates to a triarylmethane-based and rhodamine-based pigment composition, and more particularly to a triarylmethane-based and rhodamine-based pigment composition excellent in light resistance and heat resistance, and a pigment dispersion using these.
従来より、トリアリールメタン系の染料および顔料は、トナー、インクジェット用インク、カラーフィルタなどに用いられてきた（特許文献１〜４）。 Conventionally, triarylmethane dyes and pigments have been used in toners, ink-jet inks, color filters, and the like (Patent Documents 1 to 4).
しかし、トリアリールメタン系の染料および顔料には、フタロシアニン顔料等と比べると、耐熱性、耐光性が劣るという欠点があった。そこで、この欠点を解消するための試みが為されている。例えば、トリフェニルメタン染料を含むポリマーを用いたカラーフィルタの開発が試みられている（特許文献５）。また、トリアリールメタンと有機酸との塩などを用いる試みが為されている（特許文献６）。 However, triarylmethane-based dyes and pigments have the disadvantage of being inferior in heat resistance and light resistance as compared to phthalocyanine pigments and the like. Thus, attempts have been made to eliminate this drawback. For example, development of a color filter using a polymer containing a triphenylmethane dye has been attempted (Patent Document 5). Attempts have also been made to use salts of triarylmethane and organic acids (Patent Document 6).
しかしながら、上記で得られるトリアリールメタン系顔料の耐光性及び耐熱性は未だ不十分であり、製造工程も複雑であり、実用化には至っていないのが実情である。 However, the light resistance and heat resistance of the triarylmethane pigment obtained above are still insufficient, the manufacturing process is complicated, and the actual situation is that it has not been put into practical use.
そこで、本発明の目的は、耐光性及び耐熱性に優れたトリアリールメタン系顔料組成物及びこれを用いた顔料分散体を提供し、更に、耐光性及び耐熱性に優れたローダミン系顔料組成物及びこれを用いた顔料分散体を提供することである。 Therefore, an object of the present invention is to provide a triarylmethane pigment composition excellent in light resistance and heat resistance and a pigment dispersion using the same, and further to rhodamine pigment composition excellent in light resistance and heat resistance. And a pigment dispersion using the same.
本発明は、トリアリールメタン構造を有するレーキ顔料及びローダミン構造を有するレーキ顔料をアリール基を有するスルホン酸又はカルボン酸で処理することにより、大幅に顔料の耐光性及び耐熱性を向上させることを見出したことに基づいて為されたものである。 The present invention has found that the light resistance and heat resistance of a pigment are greatly improved by treating a lake pigment having a triarylmethane structure and a lake pigment having a rhodamine structure with a sulfonic acid or carboxylic acid having an aryl group. It was made based on that.
即ち、本発明の顔料組成物は、化１で表されるトリアリールメタン構造及び／又は化３で表されるローダミン構造を有するレーキ顔料から選択される未処理顔料を、置換若しくは非置換のアリールスルホン酸及び置換若しくは非置換のアリールカルボン酸からなる群から選択される有機酸で処理したことを特徴とする。 That is, the pigment composition of the present invention is an untreated pigment selected from a lake pigment having a triarylmethane structure represented by Chemical Formula 1 and / or a rhodamine structure represented by Chemical Formula 3 with a substituted or unsubstituted aryl. Treated with an organic acid selected from the group consisting of a sulfonic acid and a substituted or unsubstituted arylcarboxylic acid.
ここで、化１において、Ｒ1、Ｒ2、Ｒ3、Ｒ4は、互いに独立して、−Ｈ、−ＣＨ3、Ｃ2Ｈ5、−Ｐｈ（フェニル基）、−ＰｈＣＨ3、−ＣＨ2Ｐｈ（ＳＯ3・１／２Ｂａ）、又は−ＣＨ2Ｐｈ（ＳＯ3・１／２Ａｌ）であり、Ｒは、化２に示す置換又は非置換のフェニル基又はナフチル基であり、 Here, in Chemical Formula 1, R 1 , R 2 , R 3 and R 4 are independently of each other —H, —CH 3 , C 2 H 5 , —Ph (phenyl group), —PhCH 3 , —CH. 2 Ph (SO 3 · 1 / 2Ba) or —CH 2 Ph (SO 3 · 1 / 2Al), R is a substituted or unsubstituted phenyl group or naphthyl group shown in Chemical Formula 2,
化２において、Ｒ5は、−Ｈ、−ＮＨＣＨ3、−Ｎ（ＣＨ3）2、−Ｎ（Ｃ2Ｈ5）2、−ＮＨＰｈ、又は−ＮＨＰｈ（ＣＨ3）（ＳＯ3Ｈ）若しくはその塩、Ｒ6は、−Ｈ、−Ｃｌ、又は−ＳＯ3Ｈ若しくはその塩、Ｒ7は、−ＮＨＣ2Ｈ5であり、 In the chemical formula 2, R 5 is —H, —NHCH 3 , —N (CH 3 ) 2 , —N (C 2 H 5 ) 2 , —NHPh, or —NHPh (CH 3 ) (SO 3 H) or its A salt, R 6 is —H, —Cl, or —SO 3 H or a salt thereof, R 7 is —NHC 2 H 5 ;
化３において、Ｒ8、Ｒ9、Ｒ10、Ｒ11は、互いに独立して−Ｈ、又はアルキル基であり、Ｒ12は、−Ｈ、アルキル基、又は置換若しくは非置換のフェニル基である。 In Chemical Formula 3, R 8 , R 9 , R 10 , and R 11 are each independently —H or an alkyl group, and R 12 is —H, an alkyl group, or a substituted or unsubstituted phenyl group. .
本発明の顔料分散体は、上記顔料組成物を用い、分散処理を施すことにより得られる顔料分散体である。 The pigment dispersion of the present invention is a pigment dispersion obtained by subjecting the above pigment composition to a dispersion treatment.
また、本発明の顔料分散体は、化１で表されるトリアリールメタン構造及び／又は化３で表されるローダミン構造を有するレーキ顔料から選択される未処理顔料を、置換若しくは非置換のアリールスルホン酸及び置換若しくは非置換のアリールカルボン酸からなる群から選択される有機酸の存在下に分散処理することによっても得ることができる。 In addition, the pigment dispersion of the present invention is a non-treated pigment selected from a lake pigment having a triarylmethane structure represented by Chemical Formula 1 and / or a rhodamine structure represented by Chemical Formula 3 with a substituted or unsubstituted aryl. It can also be obtained by a dispersion treatment in the presence of an organic acid selected from the group consisting of a sulfonic acid and a substituted or unsubstituted arylcarboxylic acid.
本発明のトリアリールメタン系及びローダミン系顔料組成物は、アリールスルホン酸又はアリールカルボン酸で処理することにより、顔料粒子の表面に何らかの状態変化を起こさせ、これを用いて顔料分散体を調製し、この分散体を用いて例えばカラーフィルタを作製すれば、耐光性及び耐熱性に優れた塗膜が得られる。 The triarylmethane and rhodamine pigment compositions of the present invention are treated with an aryl sulfonic acid or an aryl carboxylic acid to cause some state change on the surface of the pigment particles, and a pigment dispersion is prepared using this. If, for example, a color filter is prepared using this dispersion, a coating film excellent in light resistance and heat resistance can be obtained.
本発明において使用されるトリアリールメタン系顔料は、前述の化１に示す化学構造式のイオンを有するレーキ顔料であり、具体的には、Ｃ．Ｉ．ピグメントブルー１、Ｃ．Ｉ．ピグメントブルー１：２、Ｃ．Ｉ．ピグメントブルー９、Ｃ．Ｉ．ピグメントブルー１４、Ｃ．Ｉ．ピグメントブルー２４、Ｃ．Ｉ．ピグメントバイオレット３、Ｃ．Ｉ．ピグメントバイオレット３：１、Ｃ．Ｉ．ピグメントバイオレット３：３、Ｃ．Ｉ．ピグメントバイオレット２７、Ｃ．Ｉ．ピグメントバイオレット３９、Ｃ．Ｉ．ピグメントブルー７８、Ｃ．Ｉ．ピグメントグリーン１、Ｃ．Ｉ．ピグメントグリーン２、Ｃ．Ｉ．ピグメントグリーン４、Ｃ．Ｉ．ピグメントブルー５６、Ｃ．Ｉ．ピグメントブルー５６：１、Ｃ．Ｉ．ピグメントブルー６１、Ｃ．Ｉ．ピグメントブルー６１：１、Ｃ．Ｉ．ピグメントブルー６２等のレーキ顔料が挙げられる。 The triarylmethane pigment used in the present invention is a lake pigment having an ion of the chemical structural formula shown in Chemical Formula 1 above. I. Pigment blue 1, C.I. I. Pigment blue 1: 2, C.I. I. Pigment blue 9, C.I. I. Pigment blue 14, C.I. I. Pigment blue 24, C.I. I. Pigment violet 3, C.I. I. Pigment violet 3: 1, C.I. I. Pigment violet 3: 3, C.I. I. Pigment violet 27, C.I. I. Pigment violet 39, C.I. I. Pigment blue 78, C.I. I. Pigment green 1, C.I. I. Pigment green 2, C.I. I. Pigment green 4, C.I. I. Pigment blue 56, C.I. I. Pigment blue 56: 1, C.I. I. Pigment blue 61, C.I. I. Pigment blue 61: 1, C.I. I. And lake pigments such as CI Pigment Blue 62.
また、本発明において使用されるローダミン系顔料は、前述の化３に示す化学構造式のイオンを有するレーキ顔料であり、具体的には、ピグメントバイオレット１、ピグメントバイオレット１：１、ピグメントバイオレット２、ピグメントバイオレット２：２、ピグメントバイオレット８１、ピグメントレッド８１：１、ピグメントレッド８１：２、ピグメントレッド８１：３、ピグメントレッド８１：４、ピグメントレッド１６９、ピグメントレッド１７３等のレーキ顔料が挙げられる。 Further, the rhodamine pigment used in the present invention is a lake pigment having an ion of the chemical structural formula shown in Chemical Formula 3 above, specifically, Pigment Violet 1, Pigment Violet 1: 1, Pigment Violet 2, Examples include lake pigments such as pigment violet 2: 2, pigment violet 81, pigment red 81: 1, pigment red 81: 2, pigment red 81: 3, pigment red 81: 4, pigment red 169, and pigment red 173.
トリアリールメタン系顔料及び／又はローダミン系顔料におけるレーキ剤としては、リンタングステン酸、リンモリブデン酸、リンタングステンモリブデン酸、フェロシアニン銅、シリコンモリブデン酸、アルミニウムを例示することができる。 Examples of the lake agent in the triarylmethane pigment and / or rhodamine pigment include phosphotungstic acid, phosphomolybdic acid, phosphotungsten molybdic acid, ferrocyanine copper, silicon molybdic acid, and aluminum.
本発明において、トリアリールメタン系顔料及び／又はローダミン系顔料を処理するための有機酸は、置換若しくは非置換のアリールスルホン酸及び／又は置換若しくは非置換のアリールカルボン酸である。ここで、置換若しくは非置換のアリールスルホン酸とは、置換基を有し若しくは置換基を有していないアリール基を有するスルホン酸をいい、置換若しくは非置換のアリールカルボン酸とは、置換基を有し若しくは置換基を有していないアリール基を有するカルボン酸をいう。置換若しくは非置換のアリールスルホン酸としては、ベンゼンスルホン酸、ナフタレンスルホン酸、メチルベンゼンスルホン酸、ジメチルベンゼンスルホン酸などのアルキルベンゼンスルホン酸、アルキルナフタレンスルホン酸、ジアルキルナフタレンスルホン酸などが挙げられ、さらに、ピリジンスルホン酸などヘテロ環を含むものでもよい。また、いずれにおいてもアミノ基やヒドロキシル基で置換されてもよく、ナトリウム、カルシウムやカリウムなどの塩でもよい。これらの酸の具体例として、化４に示す、２−ナフタレンスルホン酸ナトリウム、２−ナフタレンスルホン酸水和物、３−（２Ｈ−ベンゾトリアゾール−２−イル）−５−ｓｅｃ−ブチル−４−ヒドロキシベンゼンスルホン酸ナトリウム、パラスチレンスルホン酸ナトリウム、３−メチル−１−（４−スルホフェニル）−５−ピラゾロン等を挙げることができる。また、置換若しくは非置換のアリールカルボン酸としては、安息香酸（ベンゼンカルボン酸）、フタル酸、トリメリット酸、ナフトエ酸（ナフタレンカルボン酸）、化４に示すナフタレン−２，３−ジカルボン酸のようなナフタル酸（ナフタレンジカルボン酸）、また、メチル安息香酸、ジメチル安息香酸、サリチル酸（ヒドロキシ安息香酸）、フタロン酸（２−（カルボキシカルボニル)安息香酸）、ヒドロキシナフタレンカルボン酸、などの置換されたものや、さらにこれらのナトリウム、カルシウムやカリウムなどの塩でもよい。 In the present invention, the organic acid for treating a triarylmethane pigment and / or a rhodamine pigment is a substituted or unsubstituted arylsulfonic acid and / or a substituted or unsubstituted arylcarboxylic acid. Here, the substituted or unsubstituted aryl sulfonic acid refers to a sulfonic acid having a substituent or an aryl group having no substituent, and the substituted or unsubstituted aryl carboxylic acid refers to a substituent. It refers to a carboxylic acid having an aryl group that has or does not have a substituent. Examples of the substituted or unsubstituted arylsulfonic acid include benzenesulfonic acid, naphthalenesulfonic acid, alkylbenzenesulfonic acid such as methylbenzenesulfonic acid, dimethylbenzenesulfonic acid, alkylnaphthalenesulfonic acid, dialkylnaphthalenesulfonic acid, and the like. It may contain a heterocycle such as pyridinesulfonic acid. In any case, it may be substituted with an amino group or a hydroxyl group, and may be a salt such as sodium, calcium or potassium. Specific examples of these acids include sodium 2-naphthalenesulfonate, 2-naphthalenesulfonic acid hydrate, 3- (2H-benzotriazol-2-yl) -5-sec-butyl-4- Examples thereof include sodium hydroxybenzenesulfonate, sodium parastyrenesulfonate, 3-methyl-1- (4-sulfophenyl) -5-pyrazolone. Examples of the substituted or unsubstituted arylcarboxylic acid include benzoic acid (benzenecarboxylic acid), phthalic acid, trimellitic acid, naphthoic acid (naphthalenecarboxylic acid), and naphthalene-2,3-dicarboxylic acid shown in Chemical formula 4 Naphthalic acid (naphthalenedicarboxylic acid), methylbenzoic acid, dimethylbenzoic acid, salicylic acid (hydroxybenzoic acid), phthalonic acid (2- (carboxycarbonyl) benzoic acid), hydroxynaphthalenecarboxylic acid, etc. In addition, these salts such as sodium, calcium and potassium may be used.
本発明におけるアリールスルホン酸及び／又はアリールカルボン酸による「処理」とは、上記未処理顔料の表面にこれらの酸をコーティングする処理を含み、典型的には、アリールスルホン酸及び／又はアリールカルボン酸の溶液に上記未処理顔料を投入し、所定の温度で所定時間攪拌した後、顔料を濾過して分離することをいう。この場合のスルホン酸及び／又はカルボン酸の溶液には、酢酸、クエン酸、ギ酸、シュウ酸等の酸を添加しておくことが好ましい。これらの酸を添加することにより、顔料表面のカチオン部分を活性化させてスルホン酸の吸着を促進し、顔料の分散性を向上させることができる。酢酸を添加する場合の好ましい濃度は、０．５質量％以上であって顔料が溶解しない範囲である。また、上記処理の温度は、６０〜１００℃の範囲が好ましい。 “Treatment” with an aryl sulfonic acid and / or an aryl carboxylic acid in the present invention includes a treatment of coating these acids on the surface of the untreated pigment, and typically includes an aryl sulfonic acid and / or an aryl carboxylic acid. The above-mentioned untreated pigment is added to this solution, stirred at a predetermined temperature for a predetermined time, and then filtered to separate the pigment. In this case, it is preferable to add an acid such as acetic acid, citric acid, formic acid, or oxalic acid to the sulfonic acid and / or carboxylic acid solution. By adding these acids, the cation portion on the pigment surface can be activated to promote the adsorption of the sulfonic acid, and the dispersibility of the pigment can be improved. A preferable concentration in the case of adding acetic acid is 0.5% by mass or more and is a range in which the pigment does not dissolve. Moreover, the temperature of the said process has the preferable range of 60-100 degreeC.
本発明の分散体は、トリアリールメタン系顔料及び／又はローダミン系顔料をアリールスルホン酸及び／又はアリールカルボン酸で処理した顔料組成物を用いて溶媒に分散させたものである。分散の方法は、例えば、ペイントコンディショナー、サンドミル、アペックスミル、ディスパーマットを用いる方法を例示することができる。 The dispersion of the present invention is a dispersion in which a triarylmethane pigment and / or a rhodamine pigment is dispersed in a solvent using a pigment composition treated with an aryl sulfonic acid and / or an aryl carboxylic acid. Examples of the dispersion method include a method using a paint conditioner, a sand mill, an apex mill, and a disperse mat.
また、本発明においては、トリアリールメタン系顔料及び／又はローダミン系顔料の分散と同時にアリールスルホン酸及び／又はアリールカルボン酸による処理を行うこともできる。その場合のアリールスルホン酸及び／又はアリールカルボン酸の添加量は、未処理顔料１００質量部に対して、１〜２０質量部、好ましくは５〜２０質量部である。具体的な分散方法は、上記の顔料組成物の分散方法と同様である。 In the present invention, the treatment with aryl sulfonic acid and / or aryl carboxylic acid can be performed simultaneously with the dispersion of the triarylmethane pigment and / or rhodamine pigment. In this case, the addition amount of the aryl sulfonic acid and / or aryl carboxylic acid is 1 to 20 parts by mass, preferably 5 to 20 parts by mass with respect to 100 parts by mass of the untreated pigment. A specific dispersion method is the same as the dispersion method of the pigment composition.
本発明の顔料組成物及び顔料分散体の調製に際して、界面活性剤を添加してもよい。界面活性剤の添加により、界面活性剤が顔料表面に吸着されて顔料の分散性が向上する。本発明において使用し得る界面活性剤としては、ナフタレンスルホン酸ホルマリン縮合物、リグニンスルホン酸等のスルホン酸系のものを例示することができる。 In preparing the pigment composition and pigment dispersion of the present invention, a surfactant may be added. By adding the surfactant, the surfactant is adsorbed on the pigment surface and the dispersibility of the pigment is improved. Examples of the surfactant that can be used in the present invention include those based on sulfonic acids such as naphthalene sulfonic acid formalin condensate and lignin sulfonic acid.
本発明の顔料分散体において使用し得る溶剤としては、一般に使用される溶剤であれば特に限定されるものではないが、一般に染料に比べて顔料が耐光性良好であるといわれているとおり、顔料を溶解させないもののほうが耐熱性・耐光性にとってより好ましい。 The solvent that can be used in the pigment dispersion of the present invention is not particularly limited as long as it is a commonly used solvent, but as it is generally said that the pigment has better light resistance than the dye, the pigment It is more preferable for heat resistance and light resistance that the material does not dissolve.
以下、本発明について具体的な実施例に基づいて説明するが、本発明は以下の記載に限定されるものではない。なお、本明細書中における「部」及び「％」は、特に明示する場合を除いて、それぞれ「質量部」、「質量％」を表す。 Hereinafter, although this invention is demonstrated based on a specific Example, this invention is not limited to the following description. In the present specification, “parts” and “%” represent “parts by mass” and “mass%”, respectively, unless otherwise specified.
（実施例１）
表１に示すように、未処理のＣ．Ｉ．ピグメントブルー１を１０部と、２−ナフタレンスルホン酸ナトリウム１部とを２．５％酢酸水溶液２５０部に投入し、ディスパーで十分撹拌した後、８０℃に昇温し、２時間撹拌した。得られたスラリーをろ過し、沈殿を水洗した後、８０℃一晩乾燥して目的の顔料組成物９．９部を得た。
Example 1
As shown in Table 1, untreated C.I. I. 10 parts of Pigment Blue 1 and 1 part of sodium 2-naphthalenesulfonate were added to 250 parts of a 2.5% aqueous acetic acid solution, sufficiently stirred with a disper, heated to 80 ° C., and stirred for 2 hours. The obtained slurry was filtered, and the precipitate was washed with water and then dried at 80 ° C. overnight to obtain 9.9 parts of the target pigment composition.
この顔料組成物を５部と、プロピレングリコールモノメチルエーテルアセテート３６．７部と、高分子系分散剤（ＢＹＫ１７０、ビックケミー・ジヤパン社製）８．３部とを、φ０．５ｍｍのジルコニアビーズとともにラッカー瓶に入れ、ペイントコンディショナーで１時間分散した後、アクリル樹脂（ＳＰＣ−２０００、昭和高分子(株)）０．２部を加え、青色顔料分散体を得た。 5 parts of this pigment composition, 36.7 parts of propylene glycol monomethyl ether acetate, and 8.3 parts of a polymeric dispersant (BYK170, manufactured by Big Chemie Japan) are mixed with zirconia beads having a diameter of 0.5 mm in a lacquer bottle. And dispersed with a paint conditioner for 1 hour, and then 0.2 part of an acrylic resin (SPC-2000, Showa Polymer Co., Ltd.) was added to obtain a blue pigment dispersion.
（実施例２〜１１）
表１に示す各成分を用い、実施例１と同様にして実施例２〜１１の青色顔料分散体を得た。なお、実施例９及び１０においては、界面活性剤はＣ．Ｉ．ピグメントブルー１と２−ナフタレンスルホン酸ナトリウム１部とともに酢酸水溶液に投入した。
(Examples 2 to 11)
Using the components shown in Table 1, blue pigment dispersions of Examples 2 to 11 were obtained in the same manner as Example 1. In Examples 9 and 10, the surfactant was C.I. I. Pigment Blue 1 and 1 part of sodium 2-naphthalenesulfonate were added to an acetic acid aqueous solution.
（比較例１〜２）
表１に示す未処理顔料をそのまま使用し、プロピレングリコールモノメチルエーテルアセテート３６．７部と、高分子系分散剤（ＢＹＫ１７０、ビックケミー・ジヤパン社製）８．３部とを、φ０．５ｍｍのジルコニアビーズとともにラッカー瓶に入れ、ペイントコンディショナーで１時間分散した後、アクリル樹脂（ＳＰＣ−２０００、昭和高分子(株)）０．２部を加え、青色顔料分散体を得た。
(Comparative Examples 1-2)
Using the untreated pigment shown in Table 1 as it is, 36.7 parts of propylene glycol monomethyl ether acetate and 8.3 parts of a polymeric dispersant (BYK170, manufactured by Big Chemie Japan) were used as zirconia beads having a diameter of 0.5 mm. The mixture was placed in a lacquer bottle and dispersed with a paint conditioner for 1 hour, and then 0.2 part of an acrylic resin (SPC-2000, Showa Polymer Co., Ltd.) was added to obtain a blue pigment dispersion.
（評価）
［試験用ガラス塗板の作製］
顔料分散体を１０ｃｍ四方のガラス板にスピンコーターを用いて塗布することにより、試験用ガラス塗板を作製した。
(Evaluation)
[Preparation of glass coating for testing]
The glass dispersion plate for a test was produced by apply | coating the pigment dispersion to a 10 cm square glass plate using a spin coater.
［耐熱性の評価］
２００℃に昇温したエアバス内にガラス塗板を静置し、１時間保持した。エアバス投入前後のガラス塗板の色差（△Ｅａｂ）を測色計（ＣＭ３７００Ｄ、コニカミノルタ製）を使用して測定した。比較例１及び２の分散体の塗板を標準資料として同時にエアバスに投入し、その色差を基準（１．００）とし、これに対する各ガラス塗板の色差の比率を表１に併せて示した。
[Evaluation of heat resistance]
The glass coated plate was allowed to stand in an air bath heated to 200 ° C. and held for 1 hour. The color difference (ΔEab) of the glass coated plate before and after the introduction of the airbus was measured using a colorimeter (CM3700D, manufactured by Konica Minolta). The coated plates of the dispersions of Comparative Examples 1 and 2 were simultaneously put into an air bath as standard data, and the color difference was used as a reference (1.00). The ratio of the color difference of each glass coated plate to this was also shown in Table 1.
［耐光性の評価］
耐光性試験機（ＸＬ７５型低温サイクルキセノンウェザーメーター、スガ試験機）を用いて１８０Ｗのキセノンランプ光に２４時間暴露した。暴露前後のガラス塗板の色差（△Ｅａｂ）を測色計（ＣＭ３７００Ｄ、コニカミノルタ製）を使用して測定した。比較例１及び２に挙げた分散体の塗板を標準資料として同時にエアバスに投入し、その色差を基準（１．００）とし、これに対する各ガラス塗板の色差の比率を表１に併せて示した。
[Evaluation of light resistance]
The sample was exposed to 180 W xenon lamp light for 24 hours using a light resistance tester (XL75 type low temperature cycle xenon weather meter, Suga tester). The color difference (ΔEab) of the glass coated plate before and after exposure was measured using a colorimeter (CM3700D, manufactured by Konica Minolta). The coated plates of the dispersions listed in Comparative Examples 1 and 2 were simultaneously put into an air bath as standard data, and the color difference was set as a reference (1.00). The ratio of the color difference of each glass coated plate to this was also shown in Table 1. .
［評価結果］
実施例１〜１１の分散体を用いて作製した試験用ガラス塗板の色差（△Ｅａｂ）の比率は、耐熱性及び耐光性の試験項目において何れも１より小さく、有機酸による処理を行わない各比較例の塗板に比較して耐熱性及び耐光性に優れていることが分かる。
[Evaluation results]
The ratio of the color difference (ΔEab) of the test glass coating plates produced using the dispersions of Examples 1 to 11 is less than 1 in the heat resistance and light resistance test items, and each of the treatments with the organic acid is not performed. It turns out that it is excellent in heat resistance and light resistance compared with the coating board of a comparative example.
（実施例１２〜１３）
表２に示すように、未処理のＣ．Ｉ．ピグメントブルー１を４．６５部と、２−ナフタレンスルホン酸ナトリウム０．３５部と、プロピレングリコールモノメチルエーテルアセテート３６．７部と、高分子系分散剤（ＢＹＫ１７０、ビックケミー・ジヤパン製）８．３部と、φ０．５ｍｍジルコニアビーズとをラッカー瓶に入れ、ペイントコンディショナーで１時間分散した後、アクリル樹脂（ＳＰＣ−２０００、昭和高分子(株)）０．２部を加えて、青色顔料分散体を得た。
(Examples 12 to 13)
As shown in Table 2, untreated C.I. I. 4.65 parts of Pigment Blue 1, 0.35 parts of sodium 2-naphthalenesulfonate, 36.7 parts of propylene glycol monomethyl ether acetate, and 8.3 parts of a polymeric dispersant (BYK170, manufactured by Big Chemie Japan) And φ0.5 mm zirconia beads in a lacquer bottle and dispersed with a paint conditioner for 1 hour, and then 0.2 part of acrylic resin (SPC-2000, Showa Polymer Co., Ltd.) is added to form a blue pigment dispersion. Obtained.
（比較例３〜４）
表２に示すように、未処理の顔料を使用し、有機酸を使用しなかったことを除いて実施例１２〜１３と同様にして青色顔料分散体を得た。
(Comparative Examples 3-4)
As shown in Table 2, a blue pigment dispersion was obtained in the same manner as in Examples 12 to 13 except that an untreated pigment was used and no organic acid was used.
（比較例５）
ベーシックブルー７の５．０ｇを水２５０ｇに撹拌溶解して、ベーシックブルー７の水溶液を作成した。これとは別に、ナフタレンスルホン酸Ｎａの２．５ｇを水２００ｇに８０℃で撹拌溶解し、ナフタレンスルホン酸水溶液を作成した。５０℃撹拌下で上記ベーシックブルー７の水溶液に上記ナフタレンスルホン酸水溶液を徐々に加え、さらに２時間撹拌し、析出物をろ過、乾燥、粉砕して顔料組成物を得た。
(Comparative Example 5)
An aqueous solution of Basic Blue 7 was prepared by stirring and dissolving 5.0 g of Basic Blue 7 in 250 g of water. Separately from this, 2.5 g of Naphthalenesulfonic acid Na was stirred and dissolved in 200 g of water at 80 ° C. to prepare an aqueous solution of naphthalenesulfonic acid. The naphthalenesulfonic acid aqueous solution was gradually added to the basic blue 7 aqueous solution with stirring at 50 ° C., and further stirred for 2 hours. The precipitate was filtered, dried and pulverized to obtain a pigment composition.
（評価）
前述と同様にして試験用ガラス塗板を作製し、耐熱性及び耐光性の試験を前述と同様にして行った。その結果を表２に併せて示した。
(Evaluation)
A test glass coated plate was prepared in the same manner as described above, and heat resistance and light resistance tests were performed as described above. The results are also shown in Table 2.
［評価結果］
実施例１２〜１３の分散体を用いて作製した試験用ガラス塗板の色差（△Ｅａｂ）の比率は、耐熱性及び耐光性の試験項目において何れも１より小さく、有機酸による処理を行わない各比較例の塗板に比較して耐熱性及び耐光性に優れていることが分かる。
[Evaluation results]
The ratio of the color difference (ΔEab) of the test glass coating plates produced using the dispersions of Examples 12 to 13 is less than 1 in the heat resistance and light resistance test items, and each of the treatments with the organic acid is not performed. It turns out that it is excellent in heat resistance and light resistance compared with the coating board of a comparative example.
本発明のトリアリールメタン系及びローダミン系顔料組成物並びにこれらを用いた顔料分散体を使用すれば、優れた耐熱性及び耐光性を有する塗膜が得られるので、液晶表示装置やカラーフィルタ、有機ＥＬデイスプレイ等のカラーフィルタ等の分野の他、トナー、インクジェットインクの分野で利用可能である。 Since the coating film having excellent heat resistance and light resistance can be obtained by using the triarylmethane-based and rhodamine-based pigment compositions of the present invention and pigment dispersions using these, liquid crystal display devices, color filters, organic In addition to the field of color filters such as EL displays, the present invention can be used in the fields of toner and inkjet ink.
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| KR1020100069101A KR101730511B1 (en) | 2009-07-17 | 2010-07-16 | Pigment composition of triarylmethane and rhodamine, and pigment dispersion using the same |
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| JP2011039259A (en) * | 2009-08-11 | 2011-02-24 | Toyo Ink Mfg Co Ltd | Coloring composition for color filter, color filter, and color display device |
| WO2011102500A1 (en) | 2010-02-16 | 2011-08-25 | Ricoh Company, Ltd. | Field effect transistor, display element, image display device, and system |
| JP2015038201A (en) * | 2013-07-16 | 2015-02-26 | 住友化学株式会社 | Colored curable resin composition |
| JP2016505655A (en) * | 2012-12-03 | 2016-02-25 | キュン−イン シンセティック カンパニー リミテッドＫｙｕｎｇ−Ｉｎ Ｓｙｎｔｈｅｔｉｃ Ｃｏ．，Ｌｔｄ． | Triarylmethane dye polymer compound, blue resin composition for color filter containing the same, and color filter using the same |
| JP2016040597A (en) * | 2014-08-12 | 2016-03-24 | 株式会社Ｄｎｐファインケミカル | Coloring resin composition for color filter, color filter, and display device |
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| CN104238267B (en) * | 2013-06-17 | 2018-11-06 | 东洋油墨Sc控股株式会社 | Color composition for color filter and colour filter |
| JP6432931B2 (en) * | 2013-07-16 | 2018-12-05 | 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． | Colored curable resin composition |
| JP7064411B2 (en) * | 2018-09-19 | 2022-05-10 | 東友ファインケム株式会社 | Colored resin compositions, color filters, and display devices |
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| JP5481647B2 (en) | 2014-04-23 |
| TWI472581B (en) | 2015-02-11 |
| KR101730511B1 (en) | 2017-04-26 |
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| CN101955689A (en) | 2011-01-26 |
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