JPS59227951A - Dispersant for pigment - Google Patents
Dispersant for pigmentInfo
- Publication number
- JPS59227951A JPS59227951A JP10276983A JP10276983A JPS59227951A JP S59227951 A JPS59227951 A JP S59227951A JP 10276983 A JP10276983 A JP 10276983A JP 10276983 A JP10276983 A JP 10276983A JP S59227951 A JPS59227951 A JP S59227951A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- group
- pigments
- carbon atoms
- saturated
- 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.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 90
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000000732 arylene group Chemical group 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 abstract description 4
- 150000004982 aromatic amines Chemical class 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000012954 diazonium Substances 0.000 abstract description 2
- 150000001989 diazonium salts Chemical class 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000002966 varnish Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000020 Nitrocellulose Substances 0.000 description 4
- 239000001023 inorganic pigment Substances 0.000 description 4
- 229920001220 nitrocellulos Polymers 0.000 description 4
- 239000002687 nonaqueous vehicle Substances 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 235000019646 color tone Nutrition 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 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
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 239000004923 Acrylic lacquer Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000008049 diazo compounds Chemical group 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [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 1
- -1 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011835 investigation Methods 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
- 239000004571 lime Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は使用適性、とくに非集合性、非結晶性に優れた
アゾ系の顔料分散剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an azo pigment dispersant that is suitable for use, particularly excellent in non-aggregation and non-crystallinity.
一般に各種コーティング組成物中において鮮明な色調と
高い着色力を発揮する実用上有用な顔料は微細な粒子か
らなっている。しかしながら顔料の微細な粒子は、オフ
セットインキ、グラビアインキおよび塗料のような非水
性ビヒクルに分散する場合、安定な分散体を得ることが
難かしく製造作業上および得られる製品の価値に重要な
影響を及ぼす秤々の問題を引き起す。In general, practically useful pigments that exhibit clear color tones and high tinting power in various coating compositions are composed of fine particles. However, fine particles of pigments, when dispersed in non-aqueous vehicles such as offset inks, gravure inks and paints, make it difficult to obtain stable dispersions, which has a significant impact on manufacturing operations and the value of the resulting products. It gives rise to problems of scale.
例えば、微細な粒子からなる顔料を含む分散体は往々に
して高粘度を示し製品の分散機からの取出し、輸送が困
難となるばかりでなく更に悪い場合は貯蔵中にゲル化を
起し使用困難となることがある。捷だ異種の顔料を混合
して使用く
する場合、凝集による色分れや、沈降などの現象により
展色物（でおいて色むらや著しい着色力の低下となって
現われることがある。さらに展色物の塗膜表面に関して
は光沢の低下、レベリノグ不良等の状態不良を生ずるこ
とがある。For example, dispersions containing pigments made of fine particles often have a high viscosity, making it difficult to remove the product from the dispersion machine and transport it, and even worse, gelation occurs during storage, making it difficult to use. It may become. When using a mixture of different types of pigments, phenomena such as color separation due to aggregation and sedimentation may appear in the developed product (color unevenness or a significant decrease in coloring power. On the surface of the paint film of the developed product, poor conditions such as a decrease in gloss and poor leveling may occur.
また、顔料の分散とは直接関係しないが一部の有機顔料
では顔料の結晶状態の変化を伴う覗、象がある。Furthermore, although not directly related to the dispersion of the pigment, some organic pigments have problems associated with changes in the crystalline state of the pigment.
すなわちオフセットインキ、グラビアインキおよび塗料
等の非水性ビヒクル中でエネルギー的に不安定な顔料の
結晶粒子がその大きざ、形態を変化させて安定状態に移
行するため展色物において著るしい色相の変化、着色力
の減少、粗粒子の発生等により商品価値を損うことがあ
る。In other words, in non-aqueous vehicles such as offset inks, gravure inks, and paints, pigment crystal particles, which are energetically unstable, change their size and shape and shift to a stable state, resulting in a noticeable change in hue in the color spread. Product value may be impaired due to changes in color, decrease in coloring power, generation of coarse particles, etc.
この様に顔料の非集合性、結晶安定性を改良する目的で
これ捷でも銅フタロシアニン系およびキナクリドン系顔
料全中心とし数多くの提案がされている。As described above, for the purpose of improving the non-aggregation property and crystal stability of pigments, many proposals have been made to use copper phthalocyanine-based and quinacridone-based pigments as the main focus.
例えば特公昭４１−２４６６およびＵＳＰ２７６１８６
５に代表されるように有機顔料を母体骨核とし側鎖にス
ルフォン基、スルフォンアミド基、アミノメチル基、フ
タルイミドメチル基等の置換基を導入して得られる顔料
分散剤を混合する方法である。For example, Special Publication No. 41-2466 and USP276186
As typified by No. 5, this is a method in which a pigment dispersant obtained by using an organic pigment as a base core and introducing substituents such as a sulfone group, a sulfonamide group, an aminomethyl group, or a phthalimidomethyl group into the side chain is mixed. .
これらの方法は、非水性ビヒクル中での顔料の非集合性
、結晶安定性等に関する効果が著るしく大きな、才た顔
料組成物の製造の容易さから判断しても非常に有利な方
法である。These methods are very advantageous, judging from the ease of producing pigment compositions that have remarkable effects on pigment non-aggregation, crystal stability, etc. in non-aqueous vehicles. be.
一方、アゾ顔料についてもアセトアセドアニライド系の
黄色顔料については特公昭４５−１１０２ｆ３、特公昭
５５−４９０８７に代表されるようにカプラーとなるア
セトアセドアニライドにスルフメン酸基、カルボキシル
基等の酸性基を導入する特許が多く出願されているが、
赤色アゾ顔料については特公昭４４−１８５８８および
、特公昭５５−１０６３０で酸性基の導入が試みられて
いるに過ぎな、い。On the other hand, regarding azo pigments, as well as acetoacedoanilide yellow pigments, sulfmenic acid groups, carboxyl groups, etc. are added to acetoacedoanilide, which serves as a coupler, as typified by Japanese Patent Publication No. 45-1102f3 and Japanese Patent Publication No. 49087-1987. Many patents have been filed for introducing acidic groups in
Regarding red azo pigments, the introduction of acidic groups has only been attempted in Japanese Patent Publication No. 44-18588 and Japanese Patent Publication No. 55-10630.
これ等の方法でも赤色アゾ顔料の非集合性、結晶安定性
はかなり改良されるが、効果はなお不十分であり、そこ
で更に詳細に検討を加えた結果、ナフトールＡＳ系の不
溶性アゾ顔料の化学構造にカルボキシル基を導入し１ｃ
場合、とくに赤色系アゾ顔料の分散に有効な顔料分散剤
が得られることを見出した。Although these methods can considerably improve the non-aggregation property and crystal stability of red azo pigments, the effects are still insufficient, and as a result of further detailed investigation, the chemistry of naphthol AS-based insoluble azo pigments has been improved. 1c by introducing a carboxyl group into the structure
It has been found that a pigment dispersant particularly effective for dispersing red azo pigments can be obtained.
本発明者等は以上のようなオフセットインキ、グラビア
インキおよび塗料等の非水性のビヒクル中で生する郡々
の問題を解決するため検討を行ない、実用上優ねたアゾ
系顔料分散剤を発明したものである。The present inventors have conducted studies to solve the various problems that occur in non-aqueous vehicles such as offset inks, gravure inks, and paints, and have invented an azo pigment dispersant that is excellent in practical use. This is what I did.
すなわち本発明は、下記一般式（１）で示されるアゾ系
顔料分散剤である。That is, the present invention is an azo pigment dispersant represented by the following general formula (1).
（ただし、Ｚはベンゼン環またはナフタレン環を示す。(However, Z represents a benzene ring or a naphthalene ring.
）Ａ：直接結合、あるいはカルボン酸アミド結合を介し
、もしくは介さない置換さ
れていてもよい炭素数１〜２０の飽和
もしくは不飽和のアルキレン基才たは
アリレン基を表わす。) A: represents a saturated or unsaturated alkylene group or arylene group having 1 to 20 carbon atoms which may be substituted with or without a direct bond or a carboxylic acid amide bond.
Ｍ：１〜２価のカチオンの一当量を表わし、例えば水素
、各種金属、４級ア
ンモニウム塩を表わす。M: represents one equivalent of a mono- or divalent cation, such as hydrogen, various metals, or quaternary ammonium salt.
Ｘ、 Ｙ ：相互に独立した炭素数１〜２０の飽和また
は不飽第１」アルキル基、アリール基、ハロゲン原子、
−ＮＲ′ｌえ、
−０１ｔ′、−ＣＯＮＩ尤′Ｒ’、 −Ｓ Ｏ２Ｎ Ｒ
”Ｒ，”。X, Y: mutually independent saturated or unsaturated primary alkyl group having 1 to 20 carbon atoms, aryl group, halogen atom,
-NR'le, -01t', -CONI'R', -S O2N R
“R,”.
−Ｏ−Ｒ’、−８−Ｒ’、−ＣＮ、 −ＮＯ２、−ＮＲ
’ＣＯＲ”、−８’０２ＮＲ’Ｒ’、−ＣＯＯＲ″でＲ
’、 Ｒ’は水素原子、炭素数１〜２０の飽和−！たは
不飽和アルキル基、ア
リール基、πは炭素数１〜２０の飽
和または不飽和アルキル基を表わす。-O-R', -8-R', -CN, -NO2, -NR
'COR', -8'02NR'R', -COOR''
', R' is a hydrogen atom, saturated with 1 to 20 carbon atoms -! or an unsaturated alkyl group, an aryl group, and π represents a saturated or unsaturated alkyl group having 1 to 20 carbon atoms.
１Ｘｍ ：相互に独立したＯ〜２の整数を表わす。1Xm: Represents a mutually independent integer from O to 2.
ｎ：１〜４の整数′を表わす。n: represents an integer from 1 to 4.
なお、一般式（Ｉ）で示される顔料分散剤は特公昭４４
−１８５８８号、特公昭５５−１０６３０号公報に示さ
れている顔料分散剤に比較して少量で優７′１．た効果
が得られる。Incidentally, the pigment dispersant represented by the general formula (I) is
-18588 and Japanese Patent Publication No. 55-10630, it has an excellent 7'1. You can get the same effect.
また一般式（１）で示される顔料分散剤は母体骨格とし
て疎水性の不溶性アゾ顔料骨格を有し、極性基としてス
ルフォン酸基より溶解性の低いカルボキシル基を有する
ため、顔料粒子の水からの分離状態は良好で、製造上、
水洗が容易、乾燥上りがソフトで再分散性が良い等の利
点がある。In addition, the pigment dispersant represented by the general formula (1) has a hydrophobic insoluble azo pigment skeleton as a matrix skeleton, and has a carboxyl group, which has lower solubility than a sulfonic acid group, as a polar group. The separation condition is good, and due to manufacturing reasons,
It has advantages such as easy washing with water, soft drying and good redispersibility.
一般式（１）で表わされる顔料分散剤は、後記の製造例
で詳述するが、例えばベース成分としてカルボキシル基
を有するアリールアミンのジアゾ化合物もしくはカプラ
ー成分としてカルボキシル基ｆ 有する３−フェニルカ
ルバモイル−２一ナントール系化合物全使用し、常法に
より各々３−フェニルカルバモイル−２−ナフトールお
よびアリールアミンのジアゾニウム塩と力、７ブリング
することにより容易（て得られる。The pigment dispersant represented by the general formula (1) will be described in detail in the production example below, but for example, it is a diazo compound of an arylamine having a carboxyl group as a base component or a 3-phenylcarbamoyl-2 having a carboxyl group f as a coupler component. It can be easily obtained by using all the mononanthole compounds and buffing them with 3-phenylcarbamoyl-2-naphthol and a diazonium salt of an arylamine in a conventional manner.
本発明のアゾ系顔料分散剤は、可溶性および不溶性アゾ
顔料、縮合アゾ顔料等のアゾ系顔料の分散に用いるとき
特に好ましい効果を有するが、フタロシアニン系顔料、
キナクリドン系顔料、イソインドリノン系顔料、ペリレ
ン・ペリノン顔料、ジオキサジン系顔料、建染染料系顔
料、塩基性染料系顔料等の有機顔料およびカーボンプラ
、り、カドミウムレッド、弁柄、鉄黒、紺青、群青等の
無機顔料の分散に用いることもできる。The azo pigment dispersant of the present invention has particularly favorable effects when used for dispersing azo pigments such as soluble and insoluble azo pigments and condensed azo pigments.
Organic pigments such as quinacridone pigments, isoindolinone pigments, perylene/perinone pigments, dioxazine pigments, vat dye pigments, basic dye pigments, carbon plastic, cadmium red, Bengara, iron black, and navy blue. It can also be used for dispersing inorganic pigments such as ultramarine.
本発明に係わる一般式（１）で表わされるアゾ系顔料分
散剤の顔料に対する配合は、顔料１００Ｍ量部に対し、
０．０１〜３０重量部が好寸しい。The azo pigment dispersant represented by the general formula (1) according to the present invention is blended with the pigment based on 100 M parts of the pigment.
A suitable amount is 0.01 to 30 parts by weight.
０．０１ｍ１部より少ないと一般式（［）で表わされる
顔料分散剤の効果が得られず、寸た、３０重量部より多
く用いても用いた分の効果が得られない。If it is less than 0.01 part by weight, the effect of the pigment dispersant represented by the general formula ([) cannot be obtained, and even if it is used in an amount greater than 30 parts by weight, the effect of the pigment dispersant cannot be obtained.
本発明にかかわるアゾ系顔料分散剤を用いる顔料組成物
の調製法としては顔料粉末と本発明に係わる一般式（１
）で表わされる顔料分散剤の粉末を単に混合しても充分
目的とする効果が得られるが、ニーダ−、ロール、アト
ライター、スーパーミル、各種粉砕機等により機械的に
混合するか、顔料の水寸たは有機訂媒によるザスペンジ
ョン系に本発明に係わる一般式（１）で表わされる顔料
分散剤を含む俗′ｔ１．を添加し、顔料表面に一般式（
１）で表わされる顔料分散剤を沈着させるか、硫酸等の
強い溶解力をもつ溶媒に有機顔料と一般式（１）で表わ
される顔料分散剤を共溶解して水等の貧溶媒により共沈
させる等の緊密な混合法を行えば更に良好な結果を得名
ことが出来る。あるいは、印刷インキ、塗料の製造工程
中または後に添加することもできる。As a method for preparing a pigment composition using the azo pigment dispersant according to the present invention, pigment powder and the general formula (1
) The desired effect can be obtained by simply mixing the pigment dispersant powder represented by The general 't1. is added to the pigment surface to form the general formula (
Either the pigment dispersant represented by formula (1) is deposited, or the organic pigment and the pigment dispersant represented by general formula (1) are co-dissolved in a solvent with strong dissolving power such as sulfuric acid, and then co-precipitated with a poor solvent such as water. Even better results can be obtained by using a method of intimate mixing such as mixing. Alternatively, it can be added during or after the manufacturing process of printing inks and paints.
さらに対象顔料がアゾ顔料の場合には、通常混合力、ブ
リングと呼ばれる手法が有効である。Furthermore, when the target pigment is an azo pigment, a method usually called mixing force or bling is effective.
すなわち顔料の力、プリノグ合成時にカルボキシル基を
有するベースまたはカプラーを必要量それぞれ対応する
ベースまたはカプラーに混合することにより、極めて均
密混合された顔料組成物を得ることが出来る。That is, by mixing the required amount of a base or coupler having a carboxyl group with the corresponding base or coupler during the synthesis of the pigment, an extremely intimately mixed pigment composition can be obtained.
この様にして得られる顔料組成物は、各鍾ロジン変性樹
脂等のオフセットインキビヒクル、ライムロジンワニス
、ポリアミド樹脂フェスまたは塩化ビニル＄１脂ワニス
等のグラビアインキに使用した場合あるいはニトロセル
ロースラ。The pigment composition thus obtained can be used in offset ink vehicles such as rosin-modified resins, gravure inks such as lime rosin varnish, polyamide resin face or vinyl chloride $1 fat varnish, or nitrocellulose varnish.
カー、アミノアルキ、ド樹脂の常乾もしくは焼付は塗料
、アクリルラッカー、アミノアクリル樹脂焼付は塗料、
ウレタン系樹脂塗料等に使用した場合、顔料単独で使用
した場合に比べ分散体粘度の低下および構造粘性の減少
等良好な流動性を示すと同時に色分れ、結晶の変化等の
問題もなく印刷物あるいは塗膜の光沢が良く従って美麗
な製品を得ることが出来る。Air-drying or baking of car, aminoalky, and resin is a paint, acrylic lacquer, and baking of aminoacrylic resin is a paint.
When used in urethane resin paints, etc., it shows good fluidity, such as lower dispersion viscosity and lower structural viscosity, compared to when pigments are used alone, and at the same time, prints without problems such as color separation or crystal changes. Alternatively, the coating film has good gloss and therefore a beautiful product can be obtained.
以下に一般％（１）で表わされる代表的なアゾ系顔料分
散剤の合成法の概略ｆ ｎ造例として述べる。An outline of the synthesis method of a typical azo pigment dispersant expressed in general % (1) will be described below as an example.
製造例１
β−オキ７ナフトエ酸をベンゼンあるいはアセトン中で
等モルの塩化チオニルと還流下に１時間加熱攪拌して酸
塩化物を合成し、反応終了後、各種アミンを加えて、更
に還流下に１時間加熱攪拌して下記の力、プラー成分を
得た。Production Example 1 An acid chloride was synthesized by heating and stirring β-ox7naphthoic acid with an equimolar amount of thionyl chloride in benzene or acetone under reflux for 1 hour. After the reaction was completed, various amines were added and the mixture was further heated under reflux. The mixture was heated and stirred for 1 hour to obtain the following strength and puller components.
〈カルボキシル基を有する力、プラー成分〉これ等の力
、ブリング成分に各種ベース類をジアゾ化して力、プリ
ングすることにより下記のアゾ系顔料分散剤を得た。<Puller component having a carboxyl group> The following azo pigment dispersant was obtained by diazotizing various bases to these forces and pulling components and pulling them.
Ｈ３
下記のカルボキシル基を有するベース類を常法によりジ
アゾ化し、各種カプラー成分と力。H3 The following bases having carboxyl groups are diazotized by a conventional method, and mixed with various coupler components.
プリングすることにより各種アゾ系顔料分散剤を得た。Various azo pigment dispersants were obtained by pulling.
〈カルボキシル基を有するベース類〉 製造例３ 製造例１で得たカルホキフル基を有するカフ。<Bases having a carboxyl group> Manufacturing example 3 A cuff having a carphokyfur group obtained in Production Example 1.
ラー成分と製造例２で使用したカルボキシル′ｆｃ有す
るベース類を使用し７てジアゾ化・力，プリングを行な
い下記アゾ系顔料分散剤を得ｆ７Ｃ０製造例４
Ｈ 造例１ 、２および３で得たカルボキシルを有する
各種アゾ系顔料分散剤を中性またはアルカリ性の水中に
溶解もしくは懸濁するか、極性有機溶剤ｔｉは疎水性有
機溶剤と少量の界面活性剤を含む乳化液中に上記アゾ系
顔料分散剤を溶解もしくは懸濁した系に１〜２価の金属
イオン水溶液もしくは有機アミンを添加し加熱損はん後
、ろ過、水洗、乾燥して下記アゾ系顔料分散剤を得た。The following azo pigment dispersant was obtained by diazotization, force, and pulling using the color component and the bases having carboxyl'fc used in Production Example 2. Various azo pigment dispersants having a carboxyl group are dissolved or suspended in neutral or alkaline water, or the azo pigments are dissolved or suspended in neutral or alkaline water. An aqueous solution of mono- or divalent metal ions or an organic amine was added to a system in which the dispersant was dissolved or suspended, and after heat loss, the mixture was filtered, washed with water, and dried to obtain the following azo pigment dispersant.
Ｈ３ 以下に実施例、比較例を挙げて説明する。H3 Examples and comparative examples will be described below.
なお、アルファベットで示すアゾ系顔料分散剤の化学構
造ｉｄ製造例に表示したものと対応する。混合比は（顔
料：本発明分散剤）の重量比で表わす。In addition, the chemical structure ID of the azo pigment dispersant indicated by the alphabet corresponds to that shown in the manufacturing example. The mixing ratio is expressed as a weight ratio of (pigment:dispersant of the present invention).
比較例および実施例１〜１５ グラビアインキ試験グラ
ビア用塩化ビニルフェスに各種顔料単独（比較例）ある
いは各種顔料と製造例１〜４で示した各種アゾ系顔料分
散剤の混合物を、それぞれ顔料分が１０％あるいは、２
５係（無機顔料のとき）となるように配合してグラビア
インキ全調製し、その粘度を調べた。結果は表１の通り
で本発明によるものが流動性に優れている。Comparative Examples and Examples 1 to 15 Gravure Ink Test Various pigments alone (comparative examples) or mixtures of various pigments and various azo pigment dispersants shown in Production Examples 1 to 4 were applied to a vinyl chloride face for gravure, each having a pigment content. 10% or 2
A total gravure ink was prepared by blending the pigments in a ratio of 5 (for inorganic pigments), and the viscosity thereof was examined. The results are shown in Table 1, and the material according to the present invention has excellent fluidity.
また、該グラビアインキで印刷した印刷物の色調の鮮明
性、着色力、光沢に関する効果においても優れた効果が
得られた。In addition, excellent effects regarding the color clarity, coloring power, and gloss of printed matter printed with the gravure ink were also obtained.
表１ グラビアインキの粘度（ＢＭ型回転粘度計）子は
、無機顔料でグラビアインキ中の顔ｆ４は２５Ｌｌ）（
取計）実施例１６〜３６
焼付は塗料用アミノアルキッド樹脂フェスにを、それぞ
れ顔料分が６φあるいは、２５係（無機顔料のとき）と
なるように配合して塗料を調整し、その粘度全測定した
。その結果全表２に示す。Table 1 Viscosity of gravure ink (BM type rotational viscometer) The element is an inorganic pigment and the face f4 in the gravure ink is 25Ll) (
Measurement) Examples 16 to 36 For baking, mix the amino alkyd resin face for paints so that the pigment content is 6φ or 25 mm (for inorganic pigments), adjust the paint, and measure the total viscosity. did. The results are shown in Table 2.
なお、実施例にかかわるアミノアルキッド塗料は、流動
性、結晶の安定性に優れ、また、塗膜における色の美麗
さ、着色力の大きさ、光沢に優れていた。さらに、貯蔵
安定性についても、増粘度の変化が少なく優れていた。The aminoalkyd paints according to Examples had excellent fluidity and crystal stability, and also had excellent color beauty, coloring power, and gloss in the coating film. Furthermore, the storage stability was also excellent, with little change in the degree of viscosity increase.
表２ アミノアルキッド焼付は塗料の粘度（ＢＭ回転粘
度計）また分散安定性については用途上とくに問題とな
る色分れ安定性についての実施徊ヲもって比較する。Table 2 Amino alkyd baking is compared with actual results regarding paint viscosity (BM rotational viscometer) and dispersion stability, which is a particular problem in terms of color separation stability.
表２の実施例に示される塗料をアミノアルキ７ドワニス
で予め調製した酸化チタンのベース塗料で顔料と酸化チ
タンの比率が１／１０になるようにカットし淡色塗料を
得る。The paints shown in the examples in Table 2 are cut using a titanium oxide base paint prepared in advance with aminoalkyd 7 varnish so that the ratio of pigment to titanium oxide is 1/10 to obtain a light-colored paint.
淡色塗料を更にキシレンで稀釈し、フォード力、プｊ６
４で３０秒（２５℃）に調整し試験管注入してガラス壁
面の変ｆヒを観察した結果を表３に示す。The light colored paint was further diluted with xylene, and
The temperature was adjusted to 30 seconds (25° C.) in Step 4, the temperature was injected into a test tube, and the deformation of the glass wall surface was observed. Table 3 shows the results.
表３ × 白が完全に分離 いずれも本発明によるものが優れた結果を示す。Table 3 × White is completely separated In both cases, the method according to the present invention shows excellent results.
実施例３７〜５１
ニトロセルロースラッカーにＣ，１，ＰｉｇｍｅｎｔＢ
ｌｕｅ １５単独（比較例１）あルイはＣ，１，Ｐｉｇ
ｍｅｎｔＢｌｕｅ １５ とアゾ系顔料分散剤のＵの混
合顔料組成物を、それぞれ顔料分が５５係（でなるよう
に配合して調製した塗料の粘度を表４に示す。また同様
にして他の顔料と本発明υて係わる化合物各ｆ重との組
合せによるニトロセルロースラッカーでの粘度に関する
試験結果を表４に示す。Examples 37-51 C, 1, Pigment B on nitrocellulose lacquer
lue 15 alone (comparative example 1) Lue is C, 1, Pig
Table 4 shows the viscosity of a paint prepared by blending a mixed pigment composition of mentBlue 15 and an azo pigment dispersant U such that the pigment content is 55 parts. Table 4 shows the test results regarding the viscosity in nitrocellulose lacquer of the compounds according to the invention in combination with each weight.
いずれの場合にも本発明によるものが流動性かつ展色塗
膜における光沢・色調の鮮明性・着台力においても優ね
た結果を示した。In all cases, the composition according to the present invention showed superior results in terms of fluidity, gloss in the developed coating film, clarity of color tone, and mounting strength.
表４ ニトロセルロースラッカーの粘度（Ｂ Ｍ型ｆｔ
’［ｉ十）表４の実施例に示される塗料を５０℃に３ケ
月間貯蔵し、その後の粘度を測定した結果全表５に示す
。Table 4 Viscosity of nitrocellulose lacquer (B M type ft
'[10] The paints shown in the examples in Table 4 were stored at 50°C for 3 months, and the viscosity was measured thereafter, and the results are shown in Table 5.
表５の結果から明らかな様に本発明によるものがいずれ
も優り、た貯蔵安定性を示している。As is clear from the results in Table 5, the products according to the present invention are superior to each other and exhibit excellent storage stability.
実施例５２ アミノアクリル焼料は塗料アミノアクリル
焼付は塗料ワニスにＣ，１，Ｐｉｇ＋ｎｅｎｔＱｒａｎ
ｇｅ ３６ Ｑ’−独（比較例）あるいはＣ，１，Ｐｉ
ｇｍｅｎｔＯｒａｎｇｅ ３６とアゾ系顔料分散剤ｄの
９（Ｊ：１０の混合顔料組成物を顔料分が６チになるよ
うに調整した塗料の流動性を比較したところ、本発明に
よるものが著しく優れた結果を示した。Example 52 Aminoacrylic firing is a paint Aminoacrylic firing is a paint varnish with C, 1, Pig+nentQran
ge 36 Q'-German (comparative example) or C, 1, Pi
Comparing the fluidity of paints prepared by adjusting the pigment content of gmentOrange 36 and azo pigment dispersant d: 9 (J: 10) so that the pigment content was 6, the results showed that the one according to the present invention was significantly superior. showed that.
また上記調製塗料をアミノアクリル塗料ワニスで予め調
服したアルミペイントベースを用いて顔料とアルミの比
率が１１５に斤るよう力。Further, using an aluminum paint base prepared in advance with aminoacrylic paint varnish, the above-prepared paint was applied so that the ratio of pigment to aluminum was 115.
トした塗料においても、本発明によるものが著しく鮮明
な色調と優れた光沢を示した。Even among the painted paints, the one according to the present invention showed extremely clear color tone and excellent gloss.
実施例５３ ウレタン塗料ワニス
ウレタン塗料ワニスにＣ，１，Ｐｉｇｍｅｎｔ Ｒｅｄ
１４６単独（比較例）あるいは、Ｃ，１，、Ｐｉｇｍ
ｅｎｔ Ｒｅｄ １４６とアゾ顔料分散剤ａの９０：１
０の混合顔料組成物をそれぞれ顔料分が１θ係になるよ
うに調整した塗料の流動［住および展色塗膜の状態を比
較したところ、本発明によるものが流動性に優れかつ展
色塗膜の色：、Ｉ！、ｌ光沢にも優れていた。Example 53 Urethane paint varnish Urethane paint varnish with C, 1, Pigment Red
146 alone (comparative example) or C,1,, Pigm
ent Red 146 and azo pigment dispersant a 90:1
The fluidity of the paints prepared by adjusting the pigment content of the mixed pigment compositions of No. Color:, I! , l It was also excellent in gloss.
実施例５４ ロジン変性フェノール樹脂オフセ、トイ
ツキロジン変性フェノール樹）宿オフセットインキワニ
スにＣ，１，Ｐｉｇｍｅｎｔ Ｒｅｄ ５３単独（比較
例）あるいはＣ，１，Ｐｉｇｍｅｎｔ Ｒｅｄ ５７と
アゾ系顔料分散剤Ｃを８５：１５の割合にした混合顔料
組成物をそれぞれ顔料分が３０係になるようにしてオフ
セットインキ全調製し、その流動性を平行板型粘度計に
より比較したところ本発明によるものが著るしく優れた
結果を示した。Example 54 C,1, Pigment Red 53 alone (comparative example) or C,1, Pigment Red 57 and azo pigment dispersant C in 85:15 to rosin modified phenolic resin offset ink varnish (rosin modified phenolic resin offset ink varnish) All offset inks were prepared using mixed pigment compositions with a pigment content of 30 parts, and their fluidity was compared using a parallel plate viscometer, and the results showed that the inventive one was significantly superior. showed that.
また、印刷物においても本発明によるものが、色調の鮮
明性、着色力、透明性において優れた結果を示した。In addition, printed matter according to the present invention showed excellent results in terms of color clarity, coloring power, and transparency.
特許出願人 東洋インキ製造株式会社patent applicant Toyo Ink Manufacturing Co., Ltd.
Claims (1)
もしくは介さない置換さ れてもよい炭素数１〜２０の飽和アル キレン基またはアリレン基を示す。 Ｍ：１〜２価のカチオンの一当量を表わす。 ＸＸＹ ：相互に独立した炭素数１〜２０の飽和アルキ
ル基、アリール基、）・ ロゲン原子、−ＮＲ’Ｒ： −ＣＯＮＲ’Ｒ″Ｘ−３Ｏ
２ＮＲ’Ｒ″Ｘ−ｏ−Ｒ’、−Ｓ −Ｒ’、−ＣＮ、−
ＮＯ２、−ＮＲ’ｃｏＲ’。 −ＮＲ’５Ｏ２Ｒ−−ｃｏｏＲ″で、Ｒ′、Ｒ″は水素
原子、炭素数１〜２０の飽 和または不飽和アルキル基、アリ ール基、Ｒ″は炭素数１〜２０の飽 和または不飽和アルキル基を表わ す。 ｉ４．、ｍ ：相互に独立したθ〜２の整数を表わす。 ｎ：１〜４の整数を表わす。[Scope of Claims] 1. A pigment dispersant represented by the following general formula (1). rn (However, Z represents a benzene ring or a naphthalene ring. A: Direct bond or via a carboxylic acid amide bond,
or an optionally substituted saturated alkylene group or arylene group having 1 to 20 carbon atoms. M: represents one equivalent of a mono- to divalent cation. XXY: mutually independent saturated alkyl group having 1 to 20 carbon atoms, aryl group, ), rogene atom, -NR'R: -CONR'R''X-3O
2NR'R''X-o-R', -S -R', -CN, -
NO2, -NR'coR'. -NR'5O2R--cooR'', R' and R'' are hydrogen atoms, saturated or unsaturated alkyl groups having 1 to 20 carbon atoms, or aryl groups, and R'' is saturated or unsaturated alkyl groups having 1 to 20 carbon atoms. i4., m: Represents a mutually independent integer of θ to 2. n: Represents an integer of 1 to 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10276983A JPS59227951A (en) | 1983-06-10 | 1983-06-10 | Dispersant for pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10276983A JPS59227951A (en) | 1983-06-10 | 1983-06-10 | Dispersant for pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59227951A true JPS59227951A (en) | 1984-12-21 |
| JPH049192B2 JPH049192B2 (en) | 1992-02-19 |
Family
ID=14336372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10276983A Granted JPS59227951A (en) | 1983-06-10 | 1983-06-10 | Dispersant for pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59227951A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS61203176A (en) * | 1985-03-04 | 1986-09-09 | Dainichi Seika Kogyo Kk | Azo lake pigment composition |
| JPH01287066A (en) * | 1988-05-13 | 1989-11-17 | Fujimoto Seiyaku Kk | Novel anthranilic acid derivative |
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1983
- 1983-06-10 JP JP10276983A patent/JPS59227951A/en active Granted
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| JPH0369380B2 (en) * | 1985-03-04 | 1991-10-31 | Dainichiseika Color Chem | |
| JPS61203176A (en) * | 1985-03-04 | 1986-09-09 | Dainichi Seika Kogyo Kk | Azo lake pigment composition |
| JPH01287066A (en) * | 1988-05-13 | 1989-11-17 | Fujimoto Seiyaku Kk | Novel anthranilic acid derivative |
| WO1999061534A1 (en) * | 1998-05-28 | 1999-12-02 | Sun Chemical Corporation | Dye based aqueous pigment dispersions |
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| EP1731577A3 (en) * | 1998-05-28 | 2007-02-28 | Sun Chemical Corporation | Dye based aqueous pigment dispersions |
| JP2001172520A (en) * | 1999-12-20 | 2001-06-26 | Toyo Ink Mfg Co Ltd | Pigment dispersant, pigment composition, and pigment dispersion |
| JP2002121456A (en) * | 2000-10-19 | 2002-04-23 | Toray Ind Inc | Pigment dispersion, colorant composition and color filter |
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| US7722716B2 (en) | 2005-11-28 | 2010-05-25 | Agfa Graphics Nv | Non-aqueous dispersions of naphthol as pigments |
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| US7819969B2 (en) | 2005-11-28 | 2010-10-26 | Agfa Graphics Nv | Naphthol as colorants and their use |
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| JP2013065021A (en) * | 2006-11-02 | 2013-04-11 | Dainichiseika Color & Chem Mfg Co Ltd | Coating liquid for color filter pixel formation, and color filter |
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| KR101140952B1 (en) * | 2006-11-02 | 2012-05-16 | 다이니치 세이카 고교 가부시키가이샤 | Pigment compositions, colored compositions making use of the pigment compositions, and color filters |
| JP2008202021A (en) * | 2006-11-02 | 2008-09-04 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment composition, coloring composition using the same, and color filter |
| KR101141007B1 (en) * | 2006-11-02 | 2012-05-07 | 다이니치 세이카 고교 가부시키가이샤 | Pigment compositions, colored compositions making use of the pigment compositions, and color filters |
| US7993446B2 (en) | 2007-02-14 | 2011-08-09 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Dispersing agent for organic pigment and use thereof |
| JP2008223007A (en) * | 2007-02-14 | 2008-09-25 | Dainichiseika Color & Chem Mfg Co Ltd | Dispersant for organic pigment and its use |
| WO2008099671A1 (en) * | 2007-02-14 | 2008-08-21 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Dispersing agent for organic pigment and use thereof |
| KR101180163B1 (en) | 2007-02-14 | 2012-09-05 | 다이니치 세이카 고교 가부시키가이샤 | Dispersing agent for organic pigment and use thereof |
| JP2009029886A (en) * | 2007-07-25 | 2009-02-12 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant, pigment composition, pigment coloring agent, and coloring agent for color filter |
| JP2009197213A (en) * | 2008-01-25 | 2009-09-03 | Dainichiseika Color & Chem Mfg Co Ltd | Coupler, pigment, coloring agent, and coloring method |
| JP2010065062A (en) * | 2008-08-11 | 2010-03-25 | Dainichiseika Color & Chem Mfg Co Ltd | Dispersing agent for organic pigment, and its use |
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|---|---|
| JPH049192B2 (en) | 1992-02-19 |
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