JP2005015675A - Method for producing organic pigment subjected to adsorption treatment - Google Patents
Method for producing organic pigment subjected to adsorption treatment Download PDFInfo
- Publication number
- JP2005015675A JP2005015675A JP2003184066A JP2003184066A JP2005015675A JP 2005015675 A JP2005015675 A JP 2005015675A JP 2003184066 A JP2003184066 A JP 2003184066A JP 2003184066 A JP2003184066 A JP 2003184066A JP 2005015675 A JP2005015675 A JP 2005015675A
- Authority
- JP
- Japan
- Prior art keywords
- derivative
- adsorption
- organic pigment
- organic
- triazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000012860 organic pigment Substances 0.000 title claims abstract description 74
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000003918 triazines Chemical class 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000000524 functional group Chemical group 0.000 claims abstract description 28
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 abstract description 39
- 239000003086 colorant Substances 0.000 abstract description 6
- 239000000975 dye Substances 0.000 description 63
- 239000003973 paint Substances 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- 239000000049 pigment Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 16
- 229920000178 Acrylic resin Polymers 0.000 description 14
- 239000004925 Acrylic resin Substances 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000011324 bead Substances 0.000 description 12
- 239000000976 ink Substances 0.000 description 11
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
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- 230000002378 acidificating effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- 239000004640 Melamine resin Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 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 6
- 150000003839 salts Chemical class 0.000 description 6
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 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 4
- 238000003860 storage Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
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- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
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- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000004533 oil dispersion Substances 0.000 description 2
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- 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 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 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 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 description 1
- ZEHOVWPIGREOPO-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-[2-(4,5,6,7-tetrachloro-1,3-dioxoinden-2-yl)quinolin-8-yl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C(=O)N1C(C1=N2)=CC=CC1=CC=C2C1C(=O)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1=O ZEHOVWPIGREOPO-UHFFFAOYSA-N 0.000 description 1
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- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
【０００１】
【発明の属する技術分野】本発明は、塩基性官能基を有する有機色素誘導体またはトリアジン誘導体で吸着処理された有機顔料およびその製造方法に関する。
【０００２】
【従来の技術】有機顔料は、着色剤として、印刷インキ、塗料、プラスチック形成材料、カラーフィルター、インクジェットなどの幅広い分野で使用されているが、近年、高鮮明性、高耐候性等の要求が厳しくなっている。通常、高鮮明性、高光沢な塗膜を得るには、有機顔料を媒体中に微分散することが必須であり、一般には、高性能の分散機や、高価な分散剤を使用するため、コスト高になる。また、各種の添加剤、例えば界面活性剤などの分散剤や顔料分散樹脂を使用した場合には、分散剤、分散樹脂の有機顔料表面への吸着が不十分な場合には、粒子同士が容易に再凝集する、さらには、分散剤、分散樹脂とインキ、塗料化用の樹脂との相溶性が悪い場合にはインキ、塗料の性能低下を招くといった問題があり、汎用性に欠ける。
【０００３】
以上のような種々の問題点を解決するために、有機色素を母体骨格として側鎖に酸性基や塩基性基を置換基として有する有機色素誘導体を分散剤として使用する方法が知られている。
【０００４】
この有機色素誘導体の作用機構としては、極性官能基を有する有機色素誘導体と、有機色素誘導体の有する官能基と逆極性を有する樹脂が酸−塩基相互作用により塩を形成し溶媒中に溶解し、この塩が有機色素部分を吸着部位として有機顔料に吸着して、樹脂層が立体反発効果を示し、有機顔料の分散安定化を図ると考えられている。この有機色素誘導体を用いた方法では、ほとんどの場合、インキ、塗料化用の樹脂をそのまま分散樹脂として使用できるので、分散剤に起因する相溶性の問題がなく、汎用性に優れる。しかし、非水系で樹脂と併用で使用する場合は、有機色素部分も溶媒和されるため、有機色素誘導体の溶解性が高くなり、有機顔料への吸着率が劣り、分散安定化に必要な表面被覆率にするには、有機色素誘導体の処理量を増やす必要があり、結果として、未吸着の有機色素誘導体が増えることになり、この未吸着の有機色素誘導体は耐水性やブリード等に悪影響を与えると考えられる。逆に、水系では、樹脂の官能基を中和しているので、有機色素誘導体−樹脂の塩を形成しづらく、また、一般に中性付近のｐＨである場合が多く、吸着処理に必要な有機色素誘導体の溶解量を得ることは困難である。
【０００５】
特許文献１、特許文献２、特許文献３では、顔料に対する未吸着の有機色素誘導体を取り除き、一層吸着とすることで、ブリードや混色、耐溶剤性を改善するとともに、耐水性と耐光性を両立した性能を有する顔料型インクジェット用記録液が開示されているが、未吸着の有機色素誘導体を取り除く方法として、遠心分離、限外濾過により分離を行うため、生産性が損なわれているばかりでなく、過剰の有機色素誘導体が排出されることによる環境負荷の増加と、有機色素誘導体の使用効率が低く、高価格となる欠点があった。
【０００６】
【特許文献１】
特開２０００−２７３３８３号公報
【０００７】
【特許文献２】
特開２０００−３０３０１４号公報
【０００８】
【特許文献３】
特開２０００−３１３８３７号公報
【０００９】
【発明が解決しようとする課題】本発明は、これらの欠点がない優れた分散安定性を有する有機色素誘導体またはトリアジン誘導体を吸着処理した有機顔料の製造方法を提供することにある。
【００１０】
【課題を解決するための手段】すなわち、本発明は、塩基性官能基を有する有機色素誘導体または塩基性官能基を有するトリアジン誘導体と、有機顔料とを水中で、上記有機色素誘導体の有機色素骨格部分を吸着部位と仮定した場合の、もしくは有機色素誘導体がアリール基またはトリアジン残基を有する場合は有機色素骨格部分とアリール基もしくはトリアジン残基部分を吸着部位と仮定した場合の吸着面積、又は、トリアジン誘導体のトリアジン部分を吸着部位と仮定した場合の、もしくはトリアジン誘導体がアリール基またはアントラキノン残基を有する場合はトリアジン部分とアリール基もしくはアントラキノン残基部分を吸着部位と仮定した場合の吸着面積が有機顔料のＢＥＴ比表面積の５０％以上となる量で吸着処理することを特徴とする吸着処理有機顔料の製造方法に関する。
【００１１】
【発明の実施の形態】以下本発明について詳細に説明する。本発明に用いる有機顔料としては、印刷インキ、塗料等に使用される、カラーインデックスに記載された各種顔料が用いられ、フタロシアニン系、キナクリドン系、ベンズイミダゾロン系、アントラキノン系、ジオキサジン系、ジケトピロロピロール系、アンサンスロン系、インダンスロン系、フラバンスロン系、ペリノン系、ペリレン系、イソインドリン系、イソインドリノン系、アゾ系等が例示される。有機顔料をさらに詳細に例示すると次のとおりである。トルイジンレッド、トルイジンマルーン、ハンザエロー、ベンジジンエロー、ピラゾロンレッドなどの不溶性アゾ顔料、リソールレッド、ヘリオボルドー、ピグメントスカーレット、パーマネントレッド２Ｂなどの溶性アゾ顔料、アリザリン、インダンスロン、チオインジゴマルーンなどの建染染料からの誘導体，フタロシアニンブルー、フタロシアニングリーンなどのフタロシアニン系，キナクリドンレッド、キナクリドンマゼンタなどのキナクリドン系、ペリレンレッド、ペリレンスカーレット、ペリレンブラックなどのペリレン系、イソインドリノンエロー、イソインドリノンオレンジなどのイソインドリノン系、ピランスロンレッド、ピランスロンオレンジなどのピランスロン系、チオインジゴ系、縮合アゾ系、ベンズイミダゾロン系、その他の顔料として、フラバンスロンエロー、アシルアミドエロー、キノフタロンエロー、イソインドリンエロー、ニッケルアゾエロー、銅アゾメチンエロー、ペリノンオレンジ、アンスロンオレンジ、ジアンスラキノニルレッド、ジオキサジンバイオレット、ジケトピロロピロール等が例示できる。
【００１２】
このような顔料をカラーインデックス（Ｃ．Ｉ．）ナンバーでより具体的に例示すると次のとおりである。Ｃ．Ｉ．ピグメントエロー１２、１３、１４、１７、２０、２４、７４、８３、８６、９３、１０９、１１０、１１７、１２５、１２８、１３７、１３８、１３９ １４７、１４８、１５０、１５１、１５３、１５４、１５５、１６６、１６８、１８０、１８４ 、１８５、Ｃ．Ｉ．ピグメントオレンジ１６、３６、４３、５１、５５、５９、６１、Ｃ．Ｉ．ピグメントレッド９、４８、４９、５２、５３、５７、９７、１２２、１２３、１４９、１６８、１７７、１８０、１９２、２０２，２０６、２０７、２０９、２１５、２１６、２１７、２２０、２２３、２２４、２２６、２２７、２２８、２３８、２４０、２５４、２５５、Ｃ．Ｉ．ピグメントバイオレット１９、２３、２９、３０、３７、４０、４２、５０、Ｃ．Ｉ．ピグメントブルー１５、１５：１、１５：３、５：６、１６、２２、６０、６４、８０、Ｃ．Ｉ．ピグメントグリーン７、３６、Ｃ．Ｉ．ピグメントブラウン２３、２５、２６、Ｃ．Ｉ．ピグメントブラック３１，３２等が例示できる。
【００１３】
有機色素誘導体またはトリアジン誘導体の吸着性、脱着性を考えた場合、ロジン処理等の表面処理がされていない有機顔料を使用することが好ましい。また、有機顔料の粒径としては、特に限定されるものではないが、通常のインキや塗料に用いる有機顔料粒径範囲と同様に０．０１〜１μｍが好ましく、特に、０１〜０．１μｍが好ましい。ただし、ここでいう粒径とは電子顕微鏡などで測定された平均一次粒子径を示す。
【００１４】
本発明に用いる、塩基性官能基を有する有機色素誘導体および、塩基性官能基を有するトリアジン誘導体は、下記一般式（１）または（３）で表される。
【００１５】
一般式（１）
【００１６】
【化１】
式中の記号は下記の意味を表す。
Ｑ１；有機色素残基、アントラキノン残基またはアミノ基を有するアリール基
Ｘ１；直接結合，−ＣＯＮＨ−Ｙ２−，−ＳＯ２ ＮＨ−Ｙ２− または−ＣＨ２ ＮＨＣＯＣＨ２ＮＨ−Ｙ１ −（Ｙ２；置換基を有してもよいアルキレン基またはアリーレン基を表す。）
Ｙ１；−ＮＨ−または−Ｏ−
Ｚ１；水酸基、アルコキシ基または下記一般式（２）で示される基で、ｎは１〜４の整数を表す。またｎ＝１の場合、−ＮＨ−Ｘ１−Ｑ１であってもよい。
Ｒ１、Ｒ２；それぞれ独立に置換もしくは無置換のアルキル基
ｍ；１〜６の整数
一般式（２）
【００１８】
【化２】
式中の記号は下記の意味を表す。
Ｙ３；−ＮＨ−または−Ｏ−
Ｒ３、Ｒ４；それぞれ独立に置換もしくは無置換のアルキル基またはＲ３とＲ４ とが一体となって形成されたヘテロ環
ｏ；１〜６の整数
一般式（３）
Ｑ２−（−Ｘ２−Ｙ４）ｐ
式中の記号は下記の意味を表す。
Ｑ２；有機色素残基またはアントラキノン残基
Ｘ２；直接結合、−ＣＯＮＨ−Ｙ５−，−ＳＯ２ＮＨ−Ｙ５−または−ＣＨ２ＮＨＣＯＣＨ２ＮＨ−Ｙ５−（Ｙ５は置換基を有してもよいアルキレン基またはアリーレン基を表す。）
Ｙ４；下記一般式（４）で示される基
ｐ；１〜４の整数
一般式（４）
【００２０】
【化３】
式中の記号は下記の意味を表す。
Ｒ５、Ｒ６；それぞれ独立に置換もしくは無置換のアルキル基
ｑ；１〜６の整数
上記一般式（１）のＱ１、（３）のＱ２における有機色素残基としてはフタロシアニン系色素、アゾ系色素、キナクリドン系色素、ジオキサジン系色素、アントラピリミジン系色素、アンサンスロン系色素、インダンスロン系色素、フラバンスロン系色素、ペリレン系色素、ペリノン系色素、チオインジコ系色素、イソインドリノン系色素、トリフェニルメタン系色素等の顔料または染料が挙げられる。上記一般式（１）のＱ１ におけるアミノ基を有するアリール基としては、例えばアミノフェニル基、アミノナフチル基などが挙げられ、この時ベンゼン環にはアミノ基に加え、他の置換可能な場所にハロゲン基、アミノ基、ニトロ基、水酸基、カルボキシル基、スルホン酸基、アルコキシ基、置換または無置換のアルキル基の何れかの置換基を有してもよい。
【００２２】
吸着処理に使用する分散機としては、特に限定されるものではないが、例えば、ペイントコンディショナー（レッドデビル社製）、ボールミル、サンドミル（シンマルエンタープライゼス社製「ダイノミル」等）、アトライター、パールミル（アイリッヒ社製「ＤＣＰミル」等）、コボールミル、バスケットミル、ホモミキサー、ホモジナイザー（エム・テクニック社製「クレアミックス」等）、湿式ジェットミル（ジーナス社製「ジーナスＰＹ」、ナノマイザー社製「ナノマイザー」等）等を用いることができる。コスト、処理能力等を考えた場合、メディア型分散機を使用するのが好ましい。また、メディアとしてはガラスビーズ、ジルコニアビーズ、アルミナビーズ、磁性ビーズ、ステンレスビーズ等を用いることができる。
【００２３】
塩基性を有する有機色素誘導体またはトリアジン誘導体の場合、水、あるいはｐＨ３〜７程度の酸性水溶液に溶解させる。好ましくはｐＨ３〜５である。その誘導体水溶液中に有機顔料を添加して混合、分散することで吸着処理が進行するものである。
【００２４】
塩基性官能基を有する有機色素誘導体またはトリアジン誘導体を溶解させるための酸としては、塩酸、硫酸、硝酸、燐酸、強酸と弱塩基の反応によって得られる塩類の無機化合物、カルボン酸類、スルホン酸類の有機酸等、水に溶解して酸性を示す化合物を用いることが出来る。有機酸類が好ましく、カルボン酸類が特に好ましい。
【００２５】
塩基性基を有する有機色素誘導体またはトリアジン誘導体を溶解させる為に添加する酸量としては、有機色素誘導体またはトリアジン誘導体に含まれる塩基性官能基量に対して０．１〜１０当量添加することが出来る。０．５〜５当量が好ましく、１〜２当量が特に好ましい。
【００２６】
塩基性官能基を有する有機色素誘導体またはトリアジン誘導体水溶液の濃度は、１〜１００ｍｍｏｌ／Ｌであり、１〜５０ｍｍｏｌ／Ｌが好ましい。さらに好ましくは５〜２０ｍｍｏｌ／Ｌである。
【００２７】
有機顔料の水分散体のスラリー濃度は、有機顔料固有の親水性度や、有機色素誘導体またはトリアジン誘導体を溶解させるために添加する酸量によって適正濃度が変動するため、特に限定されるものではないが、５〜１５％が好ましい。
【００２８】
分散安定化を図るには、有機顔料表面をより多くの有機色素誘導体またはトリアジン誘導体で被覆し、樹脂との親和性を上げることが必要である。具体的には、有機色素誘導体またはトリアジン誘導体部分を吸着部位と考えた場合の、有機顔料のＢＥＴ比表面積の５０％以上となる量を吸着させる必要がある。例えば、フタロシアニン誘導体を使用した場合では、フタロシアニン残基の１分子あたりの分子占有面積は１０６Å２として計算を行い、以下、同様の計算方法によって、ベンズイミダゾロン残基の１分子あたりの分子占有面積は３８Å２、トリアジン残基の分子占有面積は２７Å２アリール基１分子あたりの分子占有面積は２７Å２、アントラキノン残基の分子占有面積は５５Å２、ジオキサジン残基の分子占有面積は１６９Å２として計算を行った。
【００２９】
有機顔料に対する有機色素誘導体またはトリアジン誘導体の吸着量は、吸着処理前後の溶解量の差から求められる。つまり、吸着処理後の有機顔料分散体を遠心分離や濾過等の操作を行う事により、有機顔料に吸着していない溶解状態の有機色素誘導体またはトリアジン誘導体の濃度を吸光度等から求め、処理前後の濃度差から吸着量を決定する。さらに、前記分子占有面積から、有機色素誘導体またはトリアジン誘導体の吸着面積を決定する。
【００３０】
本発明は、有機顔料のＢＥＴ比表面積に対して、５０％以上に相当する面積を有機色素誘導体またはトリアジン誘導体で被覆し、有機顔料表面に塩基性官能基を導入し、分散安定化を図るものである。
【００３１】
吸着処理された有機顔料は、同時に、その性能を発揮させるために、分散粒径として０．５μｍ以下、好ましくは０．３μｍ以下に微細化するのが望ましい。ここでいう分散粒径とは、一般的な粒度分布計、例えば、動的光散乱方式の粒度分布計（例えば日機装社製「マイクロトラックＵＰＡ」）で測定される平均粒子径（Ｄ５０値）である。
【００３２】
未吸着の有機色素誘導体またはトリアジン誘導体は、溶解状態のため、塗膜にした後も、耐水性、ブリード等への悪影響が懸念される。インクジェット、自動車塗料等のような耐水性、ブリードへの要求が高い用途に使用する場合は、有機色素誘導体またはトリアジン誘導体の濃度と、有機顔料の添加量を調整し、添加した有機色素誘導体またはトリアジン誘導体の９０％以上が吸着するような条件とし、未吸着の有機色素誘導体またはトリアジン誘導体の量を有機顔料１ｇ当たり０．００５ｇ以下とするのが望ましい。この方法によれば、遠心分離、限外濾過等の操作により未吸着の有機色素誘導体またはトリアジン誘導体を除去する必要がなくなり、低コストで耐水性、ブリード等の問題がない処理有機顔料を得ることができる。
【００３３】
本発明によって得られる吸着処理有機顔料は溶剤系または水系のワニスによって分散することにより、インキ、塗料等用の有機顔料分散体とすることができる。ワニスに含有される樹脂の例としては、石油樹脂、カゼイン、セラック、ロジン変性マレイン酸樹脂、ロジン変性フェノール樹脂、ニトロセルロース、セルロースアセテートブチレート、環化ゴム、塩化ゴム、酸化ゴム、塩酸ゴム、フェノール樹脂、アルキド樹脂、ポリエステル樹脂、不飽和ポリエステル樹脂、アミノ樹脂、エポキシ樹脂、ビニル樹脂、塩化ビニル、塩化ビニル−酢酸ビニル共重合体、アクリル樹脂、メタクリル樹脂、ポリウレタン樹脂、シリコーン樹脂、フッ素樹脂、乾性油、合成乾性油、スチレン変性マレイン酸、ポリアミド樹脂、塩素化ポリプロピレン、ブチラール樹脂、塩化ビニリデン樹脂等が使用できる。吸着処理された有機色素誘導体またはトリアジン誘導体の塩基性官能基と逆極性をもつことが好ましい。
【００３４】
この吸着処理有機顔料は、水を除去して使用しても良いし、水系で使用する場合は、この組成物にインキ、塗料用の樹脂を混合しても使用できる。また、油系で使用する場合は、この吸着処理有機顔料組成物に、有機色素誘導体またはトリアジン誘導体の有する官能基と逆極性の官能基を有する樹脂を含むワニスを加熱しながら添加、混合し、インキ、塗料系の使用溶剤を添加し、水を取り除いた方が微細な分散体を得ることができる。
【００３５】
塩基性官能基を有する、有機色素誘導体またはトリアジン誘導体と逆極性の官能基を持つ樹脂とは、酸性官能基を含む樹脂である。酸性官能基とは、カルボン酸、リン酸、スルホン酸等であり、それら酸性官能基を含む樹脂としては、これら酸性官能基から選ばれる１種で、ポリビニル樹脂、アクリル樹脂、ポリエステル樹脂およびポリウレタン樹脂等を変性させたもの、あるいは高分子分散剤から選ばれる少なくとも１種である。これら有機色素誘導体またはトリアジン誘導体色素と逆極性を持つ樹脂が、有機顔料に吸着した有機色素誘導体またはトリアジン誘導体の官能基とがイオン結合した構造で、有機顔料の表面が樹脂で被覆されることにより、有機顔料の分散性が向上すると考えられ、樹脂の添加量としては、有機色素誘導体またはトリアジン誘導体の官能基を中和する量の１〜５倍が好ましく、１．１〜２倍が特に好ましい。
【００３６】
水を除去し、粉体として使用する場合には、吸着処理後の水分散液に、処理した有機色素誘導体またはトリアジン誘導体が有する官能基と逆極性の酸性水溶液で中和して不溶化した後、濾過するのが好ましい。中和剤としての酸は、塩酸、硫酸、硝酸、燐酸、強酸と弱塩基の反応によって得られる塩類の無機化合物、カルボン酸類、スルホン酸類の有機酸等、水に溶解して酸性を示す化合物を用いることが出来る。有機酸類が好ましく、カルボン酸類が特に好ましい。
【００３７】
本発明によって得られる吸着処理有機顔料組成物は、非水系または水系のオフセット、グラビア、筆記具、インクジェット等の各種インキや、建築、自動車、カラーフィルター等の各種塗料、プラスチック用などの着色剤等広範囲の分野に利用することができる。
【００３８】
【実施例】
以下、実施例に基づき本発明をさらに詳細に説明するが、本発明はその要旨を超えない限り、以下の実施例に特に限定されるものではない。実施例中、部および％は、それぞれ重量部および重量％を表す。なお、実施例、比較例で得られた有機顔料分散体の粒径の測定および貯蔵安定性、光沢値の測定、耐水性の評価は下記の方法で行った。
【００３９】
（１） 動的光散乱方式の粒度分布計（日機装社製「マイクロトラックＵＰＡ」）を用いて平均粒子径（Ｄ５０の値）を測定した。水性有機顔料分散体にはイオン交換水を、油性有機顔料分散体にはトルエンを希釈溶媒として使用した。
【００４０】
（２） 貯蔵安定性は、有機顔料分散体を４０℃で１０日間保存した後の粒径の変化から保存安定性を評価した。
【００４１】
（３） アクリル樹脂とメラミン樹脂を用いて塗料を作製し、中塗り板に塗工、焼き付けを行い、２０゜光沢値を測定した。
【００４２】
（４） （３）の塗板に上塗り用のクリヤーコートを塗工し、６０℃のイオン交換水中で１０日間保存し、塗面状態を観察した。
【００４３】
実施例１ ＬＩＯＮＯＬ ＢＬＵＥ Ｅ（東洋インキ社製：ＢＥＴ比表面積７０ｍ２／ｇ）２０ｇ、一般式（５）で示される銅フタロシアニン誘導体１．０ｇ、イオン交換水７９．０ｇを２２５ｃｃのガラス瓶に仕込み、混合した後、ｐＨ４．５になるように酢酸を添加しジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行い、本発明の吸着処理有機顔料の水分散体を得た。実施例１と同様の操作によりフタロシアニン誘導体の吸着量を求めた。吸着量は０．６５ｍｇ／ｍ２であり、フタロシアニンの分子占有面積を１．０６×１０−１８ｍ２とすると、表面被覆率は５４％となる。また、このときの未吸着の誘導体量は顔料１ｇあたり０．００５ｇである。希釈前の表面処理有機顔料水分散体２０ｇに水溶性アクリル樹脂Ａ（ＮＶ＝３５％、酸価６５、ＯＨ価５０、Ｍｗ＝１５０００）３２ｇとサイメル３２５（三井サイテック社製メラミン樹脂）６ｇとイオン交換水２２ｇを添加し、ディスパーで均一になるように攪拌、混合し、水性塗料を得た。
【００４４】
一般式（５）
【００４５】
【化４】
実施例２ 実施例３の希釈前の表面処理有機顔料水分散体を１０５℃の熱風オーブンで加熱して水を除去し、吸着処理有機顔料を得た。この表面処理有機顔料４ｇに油溶性アクリル樹脂Ｂ（ＮＶ＝５０％、酸価８、ＯＨ価２２、Ｍｗ＝３５０００）２２．４ｇとサイメル３０３（三井サイテック社製メラミン樹脂）４．８ｇとトルエン３５．５ｇを添加し、ディスパーで均一になるように攪拌、混合し、油性塗料を得た。
【００４７】
実施例３ ＬＩＯＮＯＬ ＲＥＤ ５６２０（東洋インキ社製：ＢＥＴ比表面積３５ｍ２／ｇ）２０ｇ、一般式（６）で示されるＰ．Ｒ．１４６誘導体０．４ｇ、イオン交換水７９．６ｇを２２５ｃｃのガラス瓶に仕込み、混合した後、ｐＨ５．０になるように酢酸を添加しジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行い、本発明の吸着処理有機顔料の水分散体を得た。実施例１と同様の操作によりＰ．Ｒ．１４６誘導体の吸着量を求めた。吸着量は０．５１ｍｇ／ｍ２であり、この有機色素残基部分の分子占有面積を１．２７×１０−１８ｍ２とすると、表面被覆率は５３％となる。また、このときの未吸着の誘導体量は顔料１ｇあたり０．００２ｇである。また、希釈前の表面処理有機顔料水分散体２０ｇに水溶性アクリル樹脂Ａ（ＮＶ＝３５％、酸価６５、ＯＨ価５０、Ｍｗ＝１５０００）３２ｇとサイメル３２５（三井サイテック社製メラミン樹脂）６ｇとイオン交換水２２ｇを添加し、ディスパーで均一になるように攪拌、混合し、水性塗料を得た。
【００４８】
一般式（６）
【００４９】
【化５】
実施例４ ＬＩＯＮＯＬ ＧＲＥＥＮ ６ＹＫ（東洋インキ社製：ＢＥＴ比表面積５２ｍ２／ｇ）２０ｇ、一般式（７）で示されるトリアジン誘導体０．６ｇ、イオン交換水７９．４ｇを２２５ｃｃのガラス瓶に仕込み、混合した後、ｐＨ５．０になるように酢酸を添加しジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行い、本発明の吸着処理有機顔料の水分散体を得た。実施例１と同様の操作によりＰ．Ｒ．１４６誘導体の吸着量を求めた。吸着量は０．５０ｍｇ／ｍ２であり、このトリアジン部分とアントラキノン残基部分の分子占有面積を１．０９×１０−１８ｍ２とすると、表面被覆率は６２％となる。また、このときの未吸着の誘導体量は顔料１ｇあたり０．００４ｇである。希釈前の表面処理有機顔料水分散体２０ｇに水溶性アクリル樹脂Ａ（ＮＶ＝３５％、酸価６５、ＯＨ価５０、Ｍｗ＝１５０００）３２ｇとサイメル３２５（三井サイテック社製メラミン樹脂）６ｇとイオン交換水２２ｇを添加し、ディスパーで均一になるように攪拌、混合し、水性塗料を得た。
【００５１】
一般式（７）
【００５２】
【化６】
実施例５ Ｈｏｓｔａｐｅｒｍ Ｙｅｌｌｏｗ Ｈ５Ｇ（クラリアント社製：ＢＥＴ比表面積２２ｍ２／ｇ）２０ｇ、一般式（８）で示されるトリアジン誘導体０．４ｇ、イオン交換水７９．６ｇを２２５ｃｃのガラス瓶に仕込み、混合した後、ｐＨ５．０になるように酢酸を添加しジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行い、本発明の吸着処理有機顔料の水分散体を得た。実施例１と同様の操作によりＰ．Ｒ．１４６誘導体の吸着量を求めた。吸着量は０．７７ｍｇ／ｍ２であり、このトリアジン誘導体の分子占有面積を０．５４×１０−１８ｍ２とすると、表面被覆率は６３％となる。また、このときの未吸着の誘導体量は顔料１ｇあたり０．００３ｇである。希釈前の表面処理有機顔料水分散体２０ｇに水溶性アクリル樹脂Ａ（ＮＶ＝３５％、酸価６５、ＯＨ価５０、Ｍｗ＝１５０００）３２ｇとサイメル３２５（三井サイテック社製メラミン樹脂）６ｇとイオン交換水２２ｇを添加し、ディスパーで均一になるように攪拌、混合し、水性塗料を得た。
【００５４】
一般式（８）
【００５５】
【化７】
【比較例】
表に示した通り、本発明の有機顔料分散体は、比較例に対して微細な分散粒径、良好な保存安定性、耐水性を示した。
【００５７】
比較例１ ＬＩＯＮＯＬ ＢＬＵＥ Ｅ ２０ｇ、一般式（５）で示される銅フタロシアニン誘導体０．４ｇ、油溶性アクリル樹脂Ｂ ２６．７ｇとトルエン５２．９ｇを２２５ｃｃのガラス瓶に仕込み、ジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行い、有機顔料の油性分散体を得た。イオン交換水の代わりにトルエンを希釈溶媒として使用した以外は実施例１と同様の操作を行い得られた表面被覆率は１３％となる。希釈前の有機顔料油性分散体２０ｇに油溶性アクリル樹脂Ｂ １７．１ｇとサイメル３０３ ４．８ｇとトルエン２４．８ｇを添加し、ディスパーで均一になるように攪拌、混合し、油性塗料を得た。
【００５８】
比較例２ ＬＩＯＮＯＬ ＢＬＵＥ Ｅ ２０ｇ、一般式（５）で示される銅フタロシアニン誘導体１．０ｇ、油溶性アクリル樹脂Ｂ ２６．７ｇとトルエン５２．３ｇを２２５ｃｃのガラス瓶に仕込み、ジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行い、有機顔料の油性分散体を得た。イオン交換水の代わりにトルエンを希釈溶媒として使用した以外は実施例１と同様の操作を行い得られた表面被覆率は４２％となる。希釈前の有機顔料油性分散体２０ｇに油溶性アクリル樹脂Ｂ １７．１ｇとサイメル３０３ ４．８ｇとトルエン２４．８ｇを添加し、ディスパーで均一になるように攪拌、混合し、油性塗料を得た。
【００５９】
比較例３ ＬＩＯＮＯＬ ＲＥＤ ５６２０ ２０ｇ、一般式（６）で示されるＰ．Ｒ．１４６誘導体０．８ｇ、水溶性アクリル樹脂Ａ ２４．５ｇとイオン交換水５４．７ｇを２２５ｃｃのガラス瓶に仕込み、ジルコニアビーズをメディアとしてペイントシェーカーを用いて１時間分散を行った。実施例１と同様の操作で得られた表面被覆率は２８％となる。希釈前の有機顔料水分散体２０ｇに水溶性アクリル樹脂Ａ ２７．１ｇとサイメル３２５ ６ｇとイオン交換水２６．９ｇを添加し、ディスパーで均一になるように攪拌、混合し、水性塗料を得た。
【００６０】
【表１】
【発明の効果】
本発明によって得られる表面吸着処理有機顔料を使用した分散体は、有機色素誘導体またはトリアジン誘導体と樹脂を混合する手法で得られる分散体、および有機色素誘導体またはトリアジン誘導体の表面被覆率が５０％以下の吸着処理有機顔料の分散体と比較して、極めて良好な分散性、保存安定性を示し、未吸着誘導体量が少ないことから良好な耐水性を示した。[0001]
TECHNICAL FIELD The present invention relates to an organic pigment adsorbed with an organic dye derivative or triazine derivative having a basic functional group and a method for producing the same.
[0002]
2. Description of the Related Art Organic pigments are used as colorants in a wide range of fields such as printing inks, paints, plastic forming materials, color filters, and ink jets. Recently, there are demands for high sharpness and high weather resistance. It is getting strict. Usually, in order to obtain a coating film with high definition and high gloss, it is essential to finely disperse the organic pigment in the medium. Generally, since a high-performance disperser or an expensive dispersant is used, High cost. In addition, when various additives such as surfactants and pigment dispersion resins are used, particles are easily separated if the dispersant or dispersion resin is not sufficiently adsorbed on the surface of the organic pigment. In addition, when the compatibility between the dispersant, the dispersion resin and the ink and the resin for coating is poor, there is a problem that the performance of the ink and the paint is lowered, and the versatility is lacking.
[0003]
In order to solve the various problems as described above, a method is known in which an organic dye derivative having an organic dye as a base skeleton and having an acidic group or a basic group as a substituent in the side chain is used as a dispersant.
[0004]
As an action mechanism of this organic dye derivative, an organic dye derivative having a polar functional group and a resin having a reverse polarity to the functional group of the organic dye derivative form a salt by acid-base interaction and dissolve in the solvent, It is considered that this salt is adsorbed on the organic pigment using the organic dye portion as an adsorption site, and the resin layer exhibits a steric repulsion effect to stabilize the dispersion of the organic pigment. In most cases, this method using an organic pigment derivative can be used as a dispersion resin as it is as a resin for forming ink or paint, so that there is no compatibility problem caused by the dispersant and excellent versatility. However, when used in combination with a resin in a non-aqueous system, the organic dye part is also solvated, so the solubility of the organic dye derivative is high, the adsorption rate to the organic pigment is poor, and the surface necessary for dispersion stabilization In order to achieve the coverage ratio, it is necessary to increase the amount of organic dye derivative to be processed. As a result, the amount of unadsorbed organic dye derivative increases, and this unadsorbed organic dye derivative has an adverse effect on water resistance and bleeding. It is thought to give. On the other hand, in the aqueous system, the functional group of the resin is neutralized, so it is difficult to form an organic dye derivative-resin salt, and generally the pH is in the vicinity of neutrality. It is difficult to obtain a dissolved amount of the pigment derivative.
[0005]
In Patent Document 1, Patent Document 2, and Patent Document 3, by removing the non-adsorbed organic dye derivative to the pigment and making it further adsorbed, it improves bleed, color mixing, and solvent resistance, and at the same time achieves both water resistance and light resistance. Although a pigment-type inkjet recording liquid having the above-mentioned performance is disclosed, as a method of removing the unadsorbed organic dye derivative, separation is performed by centrifugation or ultrafiltration, so that productivity is not only impaired. However, there are disadvantages that the environmental load increases due to the discharge of excess organic dye derivatives, and that the use efficiency of the organic dye derivatives is low and the price is high.
[0006]
[Patent Document 1]
JP 2000-273383 A
[0007]
[Patent Document 2]
JP 2000-303014 A
[0008]
[Patent Document 3]
JP 2000-313837 A
[0009]
SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing an organic pigment obtained by adsorbing an organic dye derivative or a triazine derivative having excellent dispersion stability without these drawbacks.
[0010]
That is, the present invention provides an organic dye skeleton of the above organic dye derivative in water by combining an organic dye derivative having a basic functional group or a triazine derivative having a basic functional group and an organic pigment in water. When the portion is assumed to be an adsorption site, or when the organic dye derivative has an aryl group or triazine residue, the adsorption area when the organic dye skeleton portion and the aryl group or triazine residue portion are assumed to be an adsorption site, or If the triazine part of the triazine derivative is assumed to be an adsorption site, or if the triazine derivative has an aryl group or an anthraquinone residue, the adsorption area when the triazine part and the aryl group or anthraquinone residue part are assumed to be an adsorption site is organic. Adsorption treatment with an amount that is 50% or more of the BET specific surface area of the pigment. The method for producing the adsorption process organic pigments symptoms.
[0011]
The present invention will be described in detail below. As the organic pigment used in the present invention, various pigments described in the color index used in printing inks, paints, etc. are used. Phthalocyanine, quinacridone, benzimidazolone, anthraquinone, dioxazine, diketo Examples include pyrrolopyrrole, anthanthrone, indanthrone, flavanthrone, perinone, perylene, isoindoline, isoindolinone, and azo. The organic pigment is exemplified in more detail as follows. Insoluble azo pigments such as toluidine red, toluidine maroon, Hansa yellow, benzidine yellow, pyrazolone red, soluble azo pigments such as risor red, helio bordeaux, pigment scarlet, permanent red 2B, vat dyes such as alizarin, indanthrone, thioindigo maroon Derivatives from dyes, phthalocyanines such as phthalocyanine blue and phthalocyanine green, quinacridones such as quinacridone red and quinacridone magenta, perylenes such as perylene red, perylene scarlet and perylene black, isoindolinone yellow and isoindolinone orange Pyranthrone series such as indolinone, pyranthrone red, pyranthrone orange, thioindigo, condensed azo, benzimidazolone Other pigments include flavanthrone yellow, acylamide yellow, quinophthalone yellow, isoindoline yellow, nickel azo yellow, copper azomethine yellow, perinone orange, anthrone orange, dianthraquinonyl red, dioxazine violet, diketopyrrolopyrrole Etc. can be illustrated.
[0012]
More specific examples of such pigments by color index (CI) numbers are as follows. C. I. Pigment Yellow 12, 13, 14, 17, 20, 24, 74, 83, 86, 93, 109, 110, 117, 125, 128, 137, 138, 139 147, 148, 150, 151, 153, 154, 155 166, 168, 180, 184, 185, C.I. I. Pigment orange 16, 36, 43, 51, 55, 59, 61, C.I. I. Pigment Red 9, 48, 49, 52, 53, 57, 97, 122, 123, 149, 168, 177, 180, 192, 202, 206, 207, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 238, 240, 254, 255, C.I. I. Pigment violet 19, 23, 29, 30, 37, 40, 42, 50, C.I. I. Pigment blue 15, 15: 1, 15: 3, 5: 6, 16, 22, 60, 64, 80, C.I. I. Pigment green 7, 36, C.I. I. Pigment brown 23, 25, 26, C.I. I. Examples thereof include pigment blacks 31 and 32.
[0013]
Considering the adsorptivity and desorption property of the organic dye derivative or triazine derivative, it is preferable to use an organic pigment that has not been subjected to surface treatment such as rosin treatment. Further, the particle size of the organic pigment is not particularly limited, but is preferably 0.01 to 1 μm, particularly 01 to 0.1 μm, as in the organic pigment particle size range used for ordinary inks and paints. preferable. However, the particle size referred to here indicates an average primary particle size measured by an electron microscope or the like.
[0014]
The organic dye derivative having a basic functional group and the triazine derivative having a basic functional group used in the present invention are represented by the following general formula (1) or (3).
[0015]
General formula (1)
[0016]
[Chemical 1]
The symbol in a formula represents the following meaning.
Q1An aryl group having an organic dye residue, an anthraquinone residue or an amino group
X1Direct bond, -CONH-Y2-, -SO2 NH-Y2-Or -CH2 NHCOCH2NH-Y1 -(Y2Represents an alkylene group or an arylene group which may have a substituent. )
Y1-NH- or -O-
Z1A hydroxyl group, an alkoxy group or a group represented by the following general formula (2), wherein n represents an integer of 1 to 4. When n = 1, —NH—X1-Q1It may be.
R1, R2Each independently substituted or unsubstituted alkyl group
m: an integer from 1 to 6
General formula (2)
[0018]
[Chemical formula 2]
The symbol in a formula represents the following meaning.
Y3-NH- or -O-
R3, R4Each independently a substituted or unsubstituted alkyl group or R;3And R4 Heterocycle formed with
o; an integer from 1 to 6
General formula (3)
Q2-(-X2-Y4)p
The symbol in a formula represents the following meaning.
Q2; Organic dye residue or anthraquinone residue
X2Direct bond, -CONH-Y5-, -SO2NH-Y5-Or -CH2NHCOCH2NH-Y5-(Y5Represents an alkylene group or an arylene group which may have a substituent. )
Y4Group represented by the following general formula (4)
p; an integer from 1 to 4
General formula (4)
[0020]
[Chemical Formula 3]
The symbol in a formula represents the following meaning.
R5, R6Each independently substituted or unsubstituted alkyl group
q; an integer from 1 to 6
Q in the above general formula (1)1Q of (3)2Organic dye residues in phthalocyanine dyes, azo dyes, quinacridone dyes, dioxazine dyes, anthrapyrimidine dyes, ansanthrone dyes, indanthrone dyes, flavanthrone dyes, perylene dyes, perinone dyes Examples thereof include pigments and dyes such as pigments, thioindico pigments, isoindolinone pigments, and triphenylmethane pigments. Q in the above general formula (1)1 Examples of the aryl group having an amino group in A include an aminophenyl group, an aminonaphthyl group, and the like. At this time, in addition to the amino group, a halogen group, an amino group, a nitro group, You may have a substituent in any one of a hydroxyl group, a carboxyl group, a sulfonic acid group, an alkoxy group, and a substituted or unsubstituted alkyl group.
[0022]
The disperser used for the adsorption treatment is not particularly limited. For example, a paint conditioner (manufactured by Red Devil), a ball mill, a sand mill (such as “Dynomill” manufactured by Shinmaru Enterprises), an attritor, a pearl mill (Such as “DCP mill” manufactured by Eirich), coball mill, basket mill, homomixer, homogenizer (such as “Creamix” manufactured by M Technique), wet jet mill (“Genus PY” manufactured by Genus, “Nanomizer manufactured by Nanomizer”) Or the like. In view of cost, processing capability, etc., it is preferable to use a media type dispersing machine. As the media, glass beads, zirconia beads, alumina beads, magnetic beads, stainless beads, etc. can be used.
[0023]
In the case of a basic organic pigment derivative or triazine derivative, it is dissolved in water or an acidic aqueous solution having a pH of about 3 to 7. Preferably it is pH 3-5. The adsorption treatment proceeds by adding and mixing and dispersing an organic pigment in the aqueous derivative solution.
[0024]
Acids for dissolving organic dye derivatives or triazine derivatives having a basic functional group include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, inorganic salts such as salts obtained by the reaction of strong acids and weak bases, organic compounds of carboxylic acids and sulfonic acids. A compound that shows acidity when dissolved in water, such as an acid, can be used. Organic acids are preferred, and carboxylic acids are particularly preferred.
[0025]
The amount of acid added to dissolve the organic dye derivative or triazine derivative having a basic group may be 0.1 to 10 equivalents added relative to the amount of the basic functional group contained in the organic dye derivative or triazine derivative. I can do it. 0.5-5 equivalent is preferable and 1-2 equivalent is especially preferable.
[0026]
The concentration of the organic dye derivative or triazine derivative aqueous solution having a basic functional group is 1 to 100 mmol / L, preferably 1 to 50 mmol / L. More preferably, it is 5-20 mmol / L.
[0027]
The slurry concentration of the aqueous dispersion of the organic pigment is not particularly limited because the appropriate concentration varies depending on the hydrophilicity inherent to the organic pigment and the amount of acid added to dissolve the organic dye derivative or triazine derivative. However, 5 to 15% is preferable.
[0028]
In order to stabilize the dispersion, it is necessary to coat the surface of the organic pigment with more organic dye derivatives or triazine derivatives to increase the affinity with the resin. Specifically, it is necessary to adsorb an amount that is 50% or more of the BET specific surface area of the organic pigment when the organic dye derivative or triazine derivative portion is considered as the adsorption site. For example, when a phthalocyanine derivative is used, the area occupied by one molecule of the phthalocyanine residue is 106 Å.2In the following, by the same calculation method, the molecular occupation area per molecule of benzimidazolone residue is 38Å.2The area occupied by triazine residues is 27Å2The area occupied per molecule of aryl group is 27Å2, The area occupied by anthraquinone residues is 55Å2The area occupied by dioxazine residues is 169１６2As a calculation.
[0029]
The adsorption amount of the organic dye derivative or triazine derivative with respect to the organic pigment is determined from the difference in the amount of dissolution before and after the adsorption treatment. In other words, the concentration of the organic pigment derivative or triazine derivative in a dissolved state that is not adsorbed to the organic pigment is determined from the absorbance, etc. by performing operations such as centrifugation and filtration on the organic pigment dispersion after the adsorption treatment. The amount of adsorption is determined from the concentration difference. Furthermore, the adsorption area of the organic dye derivative or triazine derivative is determined from the area occupied by the molecules.
[0030]
In the present invention, an area corresponding to 50% or more of the BET specific surface area of an organic pigment is coated with an organic dye derivative or a triazine derivative, and a basic functional group is introduced on the surface of the organic pigment to stabilize dispersion. It is.
[0031]
At the same time, the organic pigment subjected to the adsorption treatment is desirably refined to a dispersion particle size of 0.5 μm or less, preferably 0.3 μm or less, in order to exhibit its performance. The dispersed particle size here is an average particle size (D50 value) measured by a general particle size distribution meter, for example, a dynamic light scattering type particle size distribution meter (for example, “Microtrac UPA” manufactured by Nikkiso Co., Ltd.). is there.
[0032]
Since the unadsorbed organic dye derivative or triazine derivative is in a dissolved state, there is a concern about adverse effects on water resistance, bleed and the like even after the coating film is formed. When used in applications requiring high water resistance and bleed, such as inkjet and automobile paints, adjust the concentration of the organic dye derivative or triazine derivative and the amount of organic pigment added, and add the added organic dye derivative or triazine. Desirably, 90% or more of the derivative is adsorbed, and the amount of the unadsorbed organic dye derivative or triazine derivative is 0.005 g or less per gram of the organic pigment. According to this method, it is not necessary to remove the unadsorbed organic dye derivative or triazine derivative by operations such as centrifugation and ultrafiltration, and a processed organic pigment free from problems such as water resistance and bleed can be obtained at low cost. Can do.
[0033]
The adsorption-treated organic pigment obtained by the present invention can be dispersed with a solvent-based or water-based varnish to form an organic pigment dispersion for ink, paint, and the like. Examples of resins contained in the varnish include petroleum resin, casein, shellac, rosin modified maleic acid resin, rosin modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber, Phenol resin, alkyd resin, polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylic resin, methacrylic resin, polyurethane resin, silicone resin, fluorine resin, Drying oil, synthetic drying oil, styrene-modified maleic acid, polyamide resin, chlorinated polypropylene, butyral resin, vinylidene chloride resin and the like can be used. It is preferable that the organic pigment derivative or triazine derivative subjected to the adsorption treatment has a reverse polarity to the basic functional group.
[0034]
The adsorption-treated organic pigment may be used after removing water, and when used in an aqueous system, the composition may be used by mixing a resin for ink and paint. In addition, when used in an oil system, a varnish containing a resin having a functional group having a reverse polarity to the functional group of the organic dye derivative or triazine derivative is added to and mixed with this adsorption-treated organic pigment composition, A fine dispersion can be obtained by adding a solvent for ink and paint and removing water.
[0035]
The resin having a basic functional group and having a functional group opposite in polarity to the organic dye derivative or triazine derivative is a resin containing an acidic functional group. The acidic functional groups are carboxylic acid, phosphoric acid, sulfonic acid, etc., and the resins containing these acidic functional groups are one selected from these acidic functional groups, and are polyvinyl resins, acrylic resins, polyester resins and polyurethane resins. Or the like, or at least one selected from polymer dispersants. A resin having a polarity opposite to that of these organic dye derivatives or triazine derivative dyes has a structure in which the functional group of the organic dye derivative or triazine derivative adsorbed on the organic pigment is ionically bonded, and the surface of the organic pigment is coated with the resin. It is considered that the dispersibility of the organic pigment is improved, and the addition amount of the resin is preferably 1 to 5 times, particularly preferably 1.1 to 2 times the amount of neutralizing the functional group of the organic dye derivative or triazine derivative. .
[0036]
When water is removed and used as a powder, the aqueous dispersion after the adsorption treatment is neutralized with an acidic aqueous solution having a polarity opposite to the functional group of the treated organic dye derivative or triazine derivative and insolubilized. It is preferred to filter. Acids as neutralizers include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, inorganic compounds such as salts obtained by the reaction of strong acids and weak bases, carboxylic acids, organic acids such as sulfonic acids, etc. Can be used. Organic acids are preferred, and carboxylic acids are particularly preferred.
[0037]
The adsorption-treated organic pigment composition obtained by the present invention includes a wide range of non-aqueous or water-based offsets, gravure, writing instruments, various inks such as inkjet, various paints such as architecture, automobiles, color filters, and colorants for plastics. It can be used in the field of
[0038]
【Example】
EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example, this invention is not specifically limited to a following example, unless the summary is exceeded. In the examples, parts and% represent parts by weight and% by weight, respectively. In addition, the measurement of the particle diameter of organic pigment dispersions obtained in Examples and Comparative Examples, storage stability, gloss value measurement, and water resistance evaluation were performed by the following methods.
[0039]
(1) The average particle size (D50 value) was measured using a dynamic light scattering particle size distribution meter (“Microtrac UPA” manufactured by Nikkiso Co., Ltd.). Ion exchange water was used as the aqueous organic pigment dispersion, and toluene was used as the diluent solvent for the oily organic pigment dispersion.
[0040]
(2) The storage stability was evaluated based on the change in particle size after the organic pigment dispersion was stored at 40 ° C. for 10 days.
[0041]
(3) A paint was prepared using an acrylic resin and a melamine resin, coated and baked on an intermediate coating plate, and a 20 ° gloss value was measured.
[0042]
(4) A clear coat for overcoating was applied to the coated plate of (3), stored in ion exchange water at 60 ° C. for 10 days, and the coated surface state was observed.
[0043]
Example 1 LIONOL BLUE E (Toyo Ink Co., Ltd .: BET specific surface area 70 m2/ G) 20 g, 1.0 g of the copper phthalocyanine derivative represented by the general formula (5), and 79.0 g of ion-exchanged water are charged in a 225 cc glass bottle, mixed, and then acetic acid is added so that the pH is 4.5, and zirconia beads are added. Was dispersed for 1 hour using a paint shaker as a medium to obtain an aqueous dispersion of the adsorption-treated organic pigment of the present invention. The adsorption amount of the phthalocyanine derivative was determined by the same operation as in Example 1. Adsorption amount is 0.65mg / m2And the molecular occupation area of phthalocyanine is 1.06 × 10-18m2Then, the surface coverage is 54%. Further, the amount of the unadsorbed derivative at this time is 0.005 g per 1 g of the pigment. 20 g of the surface-treated organic pigment aqueous dispersion before dilution, 32 g of water-soluble acrylic resin A (NV = 35%, acid value 65, OH value 50, Mw = 15000), 6 g of Cymel 325 (melamine resin manufactured by Mitsui Cytec) and ions 22 g of exchange water was added and stirred and mixed so as to be uniform with a disper to obtain an aqueous paint.
[0044]
General formula (5)
[0045]
[Formula 4]
Example 2 The surface-treated organic pigment aqueous dispersion before dilution of Example 3 was heated in a hot air oven at 105 ° C. to remove water to obtain an adsorption-treated organic pigment. 4 g of this surface-treated organic pigment, 22.4 g of an oil-soluble acrylic resin B (NV = 50%, acid value 8, OH value 22, Mw = 35000), 4.8 g of Cymel 303 (melamine resin manufactured by Mitsui Cytec Co., Ltd.) and 35 of toluene 0.5 g was added and stirred and mixed so as to be uniform with a disper to obtain an oil-based paint.
[0047]
Example 3 LIONOL RED 5620 (Toyo Ink Co., Ltd .: BET specific surface area 35 m2/ G) 20 g, P.I. R. After adding 0.4 g of 146 derivative and 79.6 g of ion-exchanged water to a 225 cc glass bottle, mixing, acetic acid was added so that the pH was 5.0, and dispersion was performed for 1 hour using a paint shaker using zirconia beads as a medium. An aqueous dispersion of the adsorption-treated organic pigment of the present invention was obtained. In the same manner as in Example 1, P.I. R. The adsorption amount of the 146 derivative was determined. Adsorption amount is 0.51mg / m2The area occupied by the organic dye residue is 1.27 × 10-18m2Then, the surface coverage is 53%. The amount of unadsorbed derivative at this time is 0.002 g per 1 g of pigment. Further, 20 g of the surface-treated organic pigment aqueous dispersion before dilution, 32 g of water-soluble acrylic resin A (NV = 35%, acid value 65, OH value 50, Mw = 15000) and 6 g of Cymel 325 (Melamine resin manufactured by Mitsui Cytec Co., Ltd.) And 22 g of ion-exchanged water were added and stirred and mixed so as to be uniform with a disper to obtain an aqueous paint.
[0048]
General formula (6)
[0049]
[Chemical formula 5]
Example 4 LIONOL GREEN 6YK (Toyo Ink Co., Ltd .: BET specific surface area 52 m2/ G) 20 g, 0.6 g of the triazine derivative represented by the general formula (7), and 79.4 g of ion-exchanged water are charged into a 225 cc glass bottle, mixed, and then acetic acid is added so that the pH is 5.0, and zirconia beads are added. Dispersion was performed for 1 hour using a paint shaker as a medium to obtain an aqueous dispersion of the adsorption-treated organic pigment of the present invention. In the same manner as in Example 1, P.I. R. The adsorption amount of the 146 derivative was determined. Adsorption amount is 0.50mg / m2The area occupied by the triazine moiety and the anthraquinone residue is 1.09 × 10-18m2Then, the surface coverage is 62%. The amount of unadsorbed derivative at this time is 0.004 g per 1 g of pigment. 20 g of the surface-treated organic pigment aqueous dispersion before dilution, 32 g of water-soluble acrylic resin A (NV = 35%, acid value 65, OH value 50, Mw = 15000), 6 g of Cymel 325 (melamine resin manufactured by Mitsui Cytec) and ions 22 g of exchange water was added and stirred and mixed so as to be uniform with a disper to obtain an aqueous paint.
[0051]
General formula (7)
[0052]
[Chemical 6]
Example 5 Hostaperm Yellow H5G (manufactured by Clariant: BET specific surface area 22 m2/ G) 20 g, 0.4 g of the triazine derivative represented by the general formula (8) and 79.6 g of ion-exchanged water are charged into a 225 cc glass bottle and mixed, and then acetic acid is added so that the pH is 5.0, and zirconia beads are added. Dispersion was performed for 1 hour using a paint shaker as a medium to obtain an aqueous dispersion of the adsorption-treated organic pigment of the present invention. In the same manner as in Example 1, P.I. R. The adsorption amount of the 146 derivative was determined. Adsorption amount is 0.77mg / m2The molecular occupation area of this triazine derivative is 0.54 × 10-18m2Then, the surface coverage is 63%. Further, the amount of the unadsorbed derivative at this time is 0.003 g per 1 g of the pigment. 20 g of the surface-treated organic pigment aqueous dispersion before dilution, 32 g of water-soluble acrylic resin A (NV = 35%, acid value 65, OH value 50, Mw = 15000), 6 g of Cymel 325 (melamine resin manufactured by Mitsui Cytec) and ions 22 g of exchange water was added and stirred and mixed so as to be uniform with a disper to obtain an aqueous paint.
[0054]
General formula (8)
[0055]
[Chemical 7]
[Comparative example]
As shown in the table, the organic pigment dispersion of the present invention exhibited a fine dispersed particle size, good storage stability, and water resistance relative to the comparative example.
[0057]
Comparative Example 1 20 g of LIONOL BLUE E, 0.4 g of copper phthalocyanine derivative represented by the general formula (5), 26.7 g of oil-soluble acrylic resin B and 52.9 g of toluene were charged into a 225 cc glass bottle, and paint shaker using zirconia beads as a medium Was used for 1 hour to obtain an oily dispersion of an organic pigment. The surface coverage obtained by performing the same operation as in Example 1 except that toluene was used as a diluent solvent instead of ion-exchanged water was 13%. 17.1 g of oil-soluble acrylic resin B, 4.8 g of Cymel 303, and 24.8 g of toluene were added to 20 g of the organic pigment oil dispersion before dilution, and the mixture was stirred and mixed uniformly with a disper to obtain an oil-based paint. .
[0058]
Comparative Example 2 20 g of LIONOL BLUE E, 1.0 g of copper phthalocyanine derivative represented by the general formula (5), 26.7 g of oil-soluble acrylic resin B and 52.3 g of toluene were charged in a 225 cc glass bottle, and paint shaker using zirconia beads as a medium. Was used for 1 hour to obtain an oily dispersion of an organic pigment. The surface coverage obtained by performing the same operation as in Example 1 except that toluene was used as a diluent solvent instead of ion-exchanged water was 42%. 17.1 g of oil-soluble acrylic resin B, 4.8 g of Cymel 303, and 24.8 g of toluene were added to 20 g of the organic pigment oil dispersion before dilution, and the mixture was stirred and mixed uniformly with a disper to obtain an oil-based paint. .
[0059]
Comparative Example 3 LIONOL RED 5620 20 g, P.I. R. 0.8 g of 146 derivative, 24.5 g of water-soluble acrylic resin A and 54.7 g of ion-exchanged water were charged into a 225 cc glass bottle, and dispersed for 1 hour using a paint shaker using zirconia beads as a medium. The surface coverage obtained by the same operation as in Example 1 is 28%. 27.1 g of water-soluble acrylic resin A, 6 g of Cymel 325, and 26.9 g of ion-exchanged water were added to 20 g of the organic pigment aqueous dispersion before dilution, and the mixture was stirred and mixed uniformly with a disper to obtain an aqueous paint. .
[0060]
[Table 1]
【The invention's effect】
The dispersion using the surface-treated organic pigment obtained by the present invention has a surface coverage of 50% or less of the dispersion obtained by mixing the organic dye derivative or triazine derivative and the resin, and the organic dye derivative or triazine derivative. Compared with the dispersion of adsorbed organic pigment, a very good dispersibility and storage stability were obtained, and since the amount of unadsorbed derivative was small, good water resistance was exhibited.
Claims (4)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2013125265A (en) * | 2011-12-16 | 2013-06-24 | Toyo Ink Sc Holdings Co Ltd | Red colored composition for color filter, and color filter |
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| JP2013125265A (en) * | 2011-12-16 | 2013-06-24 | Toyo Ink Sc Holdings Co Ltd | Red colored composition for color filter, and color filter |
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