JPH0778180B2 - Pigment composition - Google Patents
Pigment compositionInfo
- Publication number
- JPH0778180B2 JPH0778180B2 JP62099121A JP9912187A JPH0778180B2 JP H0778180 B2 JPH0778180 B2 JP H0778180B2 JP 62099121 A JP62099121 A JP 62099121A JP 9912187 A JP9912187 A JP 9912187A JP H0778180 B2 JPH0778180 B2 JP H0778180B2
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- Japan
- Prior art keywords
- pigment
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- parts
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- compound
- Prior art date
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Description
【発明の詳細な説明】 本発明は，顔料組成物に関する。さらに詳しくは本発明
は使用適性，とくに非集合性に優れた水性顔料分散体等
を提供するに有用な顔料組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to pigment compositions. More specifically, the present invention relates to a pigment composition which is useful for providing an aqueous pigment dispersion excellent in usability, particularly non-aggregation property.
（従来の技術） 従来，塗料，繊維用捺染剤，皮革用塗料，パルプ，紙，
グラビアインキ，フレキソインキ，筆記用具インキ，ゴ
ム，絵具および石鹸などの着色剤として水性顔料分散体
を使用する方法は良く知られている。(Conventional technology) Conventionally, paints, textile printing agents, leather paints, pulp, paper,
It is well known how to use aqueous pigment dispersions as colorants for gravure inks, flexo inks, writing inks, rubbers, paints and soaps.
水性顔料分散体は顔料，水および分散剤の混合物に必要
に応じて乾燥防止剤などの添加剤を加えて，ロールミ
ル，ボールミルおよびサンドミルなどの分散機により顔
料を微細に分散したものである。The aqueous pigment dispersion is a mixture of a pigment, water and a dispersant, to which an additive such as an anti-drying agent is added if necessary, and the pigment is finely dispersed by a disperser such as a roll mill, a ball mill and a sand mill.
この水性顔料分散体に要求される機能の１つとして，顔
料の微細な分散状態が安定して保持されることがあげら
れる。One of the functions required of this water-based pigment dispersion is to stably maintain the finely dispersed state of the pigment.
具体的には水性顔料分散体の着色力，粘度および顔料粒
子径などの諸特性に対して経時変化が少ないことや前記
の種々の用途に応じたビヒクルに着色剤として添加して
混合したときに顔料凝集や色分れなどを起こさず，混合
の強さにより色相の変化が生じないことなどである。Specifically, there is little change over time in various properties such as coloring power, viscosity and pigment particle size of the aqueous pigment dispersion, and when added as a colorant to a vehicle according to the above various uses and mixed. That is, pigment aggregation and color separation do not occur, and hue does not change due to the strength of mixing.
この機能を満足させるためには分散剤の使用が不可欠で
あり，例えば非イオン性界面活性剤，アニオン性界面活
性剤，カチオン性界面活性剤および両性界面活性剤など
の界面活性剤，ならびにアクリルスチレン共重合樹脂お
よびスチレンマレイン酸樹脂などの水溶性樹脂が使用さ
れるが，必ずしも満足できる分散状態が得られる，特に
前記の種々の用途に応じたビヒクルに添加したときに，
ほとんどの場合に顔料凝集の発生が見られる。The use of dispersants is indispensable for satisfying this function. For example, surfactants such as nonionic surfactants, anionic surfactants, cationic surfactants and amphoteric surfactants, and acrylic styrene. Water-soluble resins such as copolymer resins and styrene-maleic acid resins are used, but a satisfactory dispersion state is always obtained, especially when added to vehicles according to the above various uses,
In most cases, pigment agglomeration occurs.
例えば有機顔料と非イオン性界面活性剤による水性顔料
分散体は最も一般的に使用されるが，澱粉，変性澱粉，
エチルセルロース，ヒドロキシエチルセルロースおよび
ポリビニルアルコールなどの水溶液に添加したときに顔
料凝集や過度の混合操作による顔料凝集の増大などが見
られる。また，予め水性顔料分散体を水やアルコール水
溶液で希釈した後に前記のビヒクルに添加する場合があ
るが，希釈工程のみで顔料凝集が発生することが多い。For example, aqueous pigment dispersions with organic pigments and nonionic surfactants are the most commonly used, but starch, modified starch,
When added to an aqueous solution of ethyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, etc., pigment aggregation and an increase in pigment aggregation due to excessive mixing operation are observed. Further, the aqueous pigment dispersion may be previously diluted with water or an aqueous alcohol solution and then added to the vehicle, but pigment aggregation often occurs only in the dilution step.
（発明が解決しようとする問題点） 本発明者等は従来の欠点を改良し，顔料の微細な分散状
態が安定に保持され，前記ビヒクルに添加したときに顔
料凝集の起こらない水性顔料分散体を製造するにあた
り，その必須成分としての顔料組成物を提供するもので
ある。(Problems to be Solved by the Invention) The inventors of the present invention have improved the conventional drawbacks by maintaining the fine dispersion state of the pigment stably and causing no pigment aggregation when added to the vehicle. The present invention provides a pigment composition as an essential component for the production of.
（問題点を解決するための手段） 本発明は，顔料100重量部および下記一般式〔Ｉ〕で示
される化合物0.3〜50重量部からなる顔料組成物であ
る。(Means for Solving Problems) The present invention is a pigment composition comprising 100 parts by weight of a pigment and 0.3 to 50 parts by weight of a compound represented by the following general formula [I].
一般式〔Ｉ〕 Ｐ〔Ｘ−NR（CH2CHR′−Ｏ−）mH〕ｎ （但し，一般式中,Pは有機色素残機，アントラキノン残
機またはアクリドン残機,Xは−SO2−，−CO−，−CH2−
または−CH2NHCOCH2−,Rは水素原子，アルキル基または
（CH2CHR′−Ｏ−）lH,R′は水素原子またはメチル基,n
は１〜３の整数,mとｌはそれぞれ２〜100の整数を表わ
す。） 本発明において，顔料は例えば，可溶性および不溶性ア
ゾ顔料，縮合アゾ顔料などのアゾ系顔料，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・ペリノン系顔料，ジオキサジン系顔料，
建染染料系顔料および塩基性染料系顔料などの有機顔料
ならびにカーボンブラック，酸化チタン，黄鉛，カドミ
ウムエロー，カドミウムレッド，弁柄，鉄黒，亜鉛華，
紺青および群青などの無機顔料である。Formula (I) P [X-NR (CH 2 CHR'- O-) m H ] n (where, in the general formula, P is an organic dye residue machine, anthraquinone residue machine or acridone residue machine, X is -SO 2 −, −CO−, −CH 2 −
Or -CH 2 NHCOCH 2 -, R is a hydrogen atom, an alkyl group or (CH 2 CHR'-O-) lH , R ' is a hydrogen atom or a methyl radical, n
Is an integer of 1 to 3, m and l are integers of 2 to 100, respectively. In the present invention, the pigment includes, for example, azo pigments such as soluble and insoluble azo pigments and condensed azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, perylene / perinone pigments, dioxazine pigments,
Organic pigments such as vat dye pigments and basic dye pigments, as well as carbon black, titanium oxide, yellow lead, cadmium yellow, cadmium red, red iron oxide, iron black, zinc white,
Inorganic pigments such as dark blue and ultramarine.
本発明に係わる一般式〔Ｉ〕の化合物は，有機顔料など
の誘導体であり、Ｐの有機色素としては，例えばフタロ
シアニン系，アゾ系，アントラキノン系，キナクリドン
系，ジオキサジン系，アントラピリジン系，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，ペリレン系およびチオインジゴ系などである。The compound of the general formula [I] according to the present invention is a derivative such as an organic pigment, and as the organic dye of P, for example, phthalocyanine type, azo type, anthraquinone type, quinacridone type, dioxazine type, anthrapyridine type, ansanthrone System, indanthrone system, flavanthrone system, perinone system, perylene system and thioindigo system.
本発明において，一般式〔Ｉ〕の化合物の，顔料に対す
る配合は，顔料100重量部に対して0.3〜50重量部が好ま
しい。0.3重量部より少ないと得られる水性顔料分散体
は顔料の微細な分散状態が安定に保たれず,50重量部よ
り多く用いても用いただけの効果が得られない。In the present invention, the compound of the general formula [I] is preferably added in an amount of 0.3 to 50 parts by weight per 100 parts by weight of the pigment. If the amount is less than 0.3 part by weight, the resulting aqueous pigment dispersion cannot stably maintain the finely dispersed state of the pigment, and even if it is used in an amount more than 50 parts by weight, the effect only for use cannot be obtained.
本発明の一般式〔Ｉ〕の化合物は前記したように市販の
ほとんどの顔料に対して効果があるが，用いる顔料と類
似の色相又は無色に近い一般式〔Ｉ〕の化合物を用いた
色相の変化が少ないので工業的に有利である。As described above, the compound of the general formula [I] of the present invention is effective for most commercially available pigments, but it has a similar hue to that of the pigment to be used or a hue using a compound of the general formula [I] which is almost colorless. Since there is little change, it is industrially advantageous.
本発明の顔料組成物の製造方法はたとえば顔料と一般式
〔Ｉ〕の化合物を粉体で混合する方法および両者の水ま
たは有機溶剤による懸濁液を混合し，次いで，水または
有機溶剤を除去する方法が一般的であるが，アゾ系顔料
においてはカップリング工程中，フタロシアニン系顔
料，キナクリドン系顔料およびジオキサジン系顔料など
においてはソルトミリング法および硫酸溶解法などの顔
料化工程中に混合することもできる。さらに最も簡便な
方法は顔料と一般式〔Ｉ〕の化合物の両者の水ケーキと
若干の水を加えて混合し，水を除去することなく続いて
水性顔料分散体などを製造する方法である。The method for producing the pigment composition of the present invention includes, for example, a method of mixing the pigment and the compound of the general formula [I] in powder form and a suspension of both of them in water or an organic solvent, and then removing the water or the organic solvent. Generally, the azo pigments should be mixed during the coupling step, and the phthalocyanine pigments, quinacridone pigments and dioxazine pigments should be mixed during the pigmentation step such as the salt milling method and the sulfuric acid dissolution method. You can also The simplest method is a method in which a water cake of both the pigment and the compound of the general formula [I] is mixed with a small amount of water and then mixed to produce an aqueous pigment dispersion or the like without removing water.
本発明に用いる一般式〔Ｉ〕の化合物の製造方法は，常
法により有機色素，アントラキノンまたはアクリドンに
−SO2Cl,−COCl,−CH2Clまたは−CH2NHCOCH2Clの置換基
を導入し，モノまたはビス−（ポリオキシアルキレン）
アミンと，水，アルコール，アセトンおよびN,N−ジメ
チルホルムアミドなどの反応溶媒中で，場合によっては
アルカリ触媒を添加して反応させ，溶媒を除去する方法
が一般的であるが，アゾ系のような有機色素においては
ジアゾ成分またはカップラー成分に予めモノまたはビス
−（ポリオキシアルキレン）アミンを反応させた後に，
カップリングする方法が工業的に有利である。The method of producing the compound of the general formula [I] used in the present invention is a conventional method in which a substituent of --SO 2 Cl, --COCl, --CH 2 Cl or --CH 2 NHCOCH 2 Cl is introduced into an organic dye, anthraquinone or acridone. Mono or bis- (polyoxyalkylene)
Amine is generally reacted with a reaction solvent such as water, alcohol, acetone and N, N-dimethylformamide by adding an alkali catalyst, and the solvent is generally removed. In organic dyes, the diazo component or the coupler component is previously reacted with mono- or bis- (polyoxyalkylene) amine,
The method of coupling is industrially advantageous.
本発明の顔料組成物を用いると，従来になく，流動性が
優れ着色力，粘度および顔料粒子などに対して経時変化
の少ない水性顔料分散体が得られる。また，水性顔料分
散体を前記の種々の用途に応じたビヒクルに着色剤とし
て添加して混合したときの顔料凝集の発生は従来から最
も改良が望まれていた問題点であるが，本発明の顔料組
成物を用いると顔料凝集はほとんど発生しない。さらに
従来は水性顔料分散体の必須成分であった界面活性剤や
水溶性樹脂などの分散剤の添加を必ずしも必要とせず，
添加しなくても充分に効果が認められる。By using the pigment composition of the present invention, it is possible to obtain an aqueous pigment dispersion having excellent flowability and little change with time in respect of coloring power, viscosity, pigment particles, etc. Further, the occurrence of pigment aggregation when an aqueous pigment dispersion is added as a colorant to a vehicle according to the above-mentioned various uses and mixed is a problem that has been most desired to be improved. When the pigment composition is used, pigment aggregation hardly occurs. Furthermore, it is not always necessary to add a dispersant such as a surfactant or a water-soluble resin, which has been an essential component of an aqueous pigment dispersion in the past.
Even if it is not added, a sufficient effect is recognized.
また，本発明の顔料組成物をアルキッド樹脂塗料，アク
リル樹脂塗料，グラビアインキおよびオイルインキなど
の油性の用途に用いても効果が認められる。Further, the effect is recognized when the pigment composition of the present invention is used for oily applications such as alkyd resin paints, acrylic resin paints, gravure inks and oil inks.
なお，本発明の顔料組成物は，顔料および一般式〔Ｉ〕
の化合物からなるもの，顔料，一般式〔Ｉ〕の化合物お
よび水からなるもの，顔料，一般式〔Ｉ〕の化合物，水
溶性樹脂などの樹脂および水からなるもの，顔料，一般
式〔Ｉ〕の化合物，界面活性剤および水からなるもの，
などを示し，水性顔料分散体の元となる組成物は勿論，
水性顔料分散体そのもの，などである。The pigment composition of the present invention comprises a pigment and a compound of the general formula [I]
Of a compound of formula (I), a compound of formula [I] and water, a pigment, a compound of formula [I], a resin such as a water-soluble resin and water, a pigment of formula [I] Consisting of a compound of, a surfactant and water,
And the composition that is the basis of the aqueous pigment dispersion,
For example, the aqueous pigment dispersion itself.
（作 用） 本発明の顔料組成物を用いると，得られる水性顔料分散
体などの諸特性が優れるという機構については必ずしも
明らかにはなっていないが，顔料粒子表面に一般式
〔Ｉ〕の化合物が強固に吸着し，その立体障害的な安定
化効果に基づくものと推定できる。(Operation) The mechanism by which the pigment composition of the present invention is excellent in various properties such as an aqueous pigment dispersion obtained is not clear, but the compound of the general formula [I] is formed on the surface of the pigment particle. Is strongly adsorbed, and it can be presumed that it is based on the sterically hindering stabilizing effect.
以下に本発明の顔料組成物に用いる化合物の合成法の概
略を製造例として述べる。例中，「部」とは「重量部」
を表わす。The outline of the method for synthesizing the compound used in the pigment composition of the present invention will be described below as a production example. In the examples, "part" means "part by weight"
Represents
製造例 １ 銅フタロシアニン（C.I.Pigment Blue 15）を常法によ
りクロロスルホン化して得たクロロスルホニル銅フタロ
シアニン135部,N,N−ビス−（ポリオキシエチレン）ア
ミン（但し，エチレンオキサイドの平均重合モル数は25
モル）490部，炭酸ナトリウム21部および水2000部を混
合し,80℃で１時間保持する。次いで濾過，水洗して化
合物（ａ）460部を含むペーストを得た。Production Example 1 135 parts of chlorosulfonyl copper phthalocyanine obtained by chlorosulfonation of copper phthalocyanine (CIPigment Blue 15) by an ordinary method, N, N-bis- (polyoxyethylene) amine (however, the average number of moles of polymerization of ethylene oxide is twenty five
(Mole) 490 parts, sodium carbonate 21 parts and water 2000 parts are mixed and kept at 80 ° C. for 1 hour. Then, the mixture was filtered and washed with water to obtain a paste containing 460 parts of compound (a).
製造例 ２ クロロメチル銅フタロシアニン125部,N,N−ビス−（ポ
リオキシプロピレン）アミン（但し，プロピレンオキサ
イドの平均重合モル数は15モル）390部およびメタノー
ル2000部を混合し,65℃で３時間保持する。次いで濾
過，水洗して化合物（ｂ）420部を含むペーストを得
た。Production Example 2 125 parts of chloromethylcopper phthalocyanine, 390 parts of N, N-bis- (polyoxypropylene) amine (however, the average number of moles of propylene oxide polymerized is 15 moles) and 2000 parts of methanol are mixed, and the mixture is mixed at 65 ° C for 3 Hold for time. Then, the mixture was filtered and washed with water to obtain a paste containing 420 parts of compound (b).
製造例 ３ Ｎ−ポリオキシエチレン−４−アセトアセチルアミノベ
ンゼンスルホニルアミド（但し，エチレンオキサイドの
重合モル数は20モル）454部と水2000部の懸濁液と4,4−
ジクロルベンジン51部を常法によりジアゾ化したジアゾ
ニウム液とをカップリングし，濾過，水洗して化合物
（ｃ）495部を含むペーストを得た。Production Example 3 N-polyoxyethylene-4-acetoacetylaminobenzenesulfonylamide (however, the polymerization mole number of ethylene oxide is 20 moles) 454 parts and water 2000 parts suspension 4,4-
51 parts of dichlorbenzine was diazotized by a conventional method and coupled with a diazonium solution, which was filtered and washed with water to obtain a paste containing 495 parts of compound (c).
製造例 ４ アントラキノン−２−カルボニルクロリド54部,N,N−ビ
ス−（ポリオキシエチレン）アミン（但し，エチレンオ
キサイドの重合モル数は20モル）355部およびアセトン2
000部を混合し,55℃で１時間撹拌する。Production Example 4 54 parts of anthraquinone-2-carbonyl chloride, 355 parts of N, N-bis- (polyoxyethylene) amine (however, the number of moles of ethylene oxide polymerized is 20 mol) and acetone 2
000 parts are mixed and stirred at 55 ° C for 1 hour.
次いで，水5000部を加えて，濾過，水洗して化合物
（ｄ）370部を含むペーストを得た。Next, 5000 parts of water was added, and the mixture was filtered and washed with water to obtain a paste containing 370 parts of compound (d).
製造例 ５〜16 製造例１〜４に準じて表１に示す化合物（ｅ）〜（ｐ）
を合成した。Production Examples 5 to 16 Compounds (e) to (p) shown in Table 1 according to Production Examples 1 to 4
Was synthesized.
次に製造例で得られた一般式〔Ｉ〕の化合物と顔料とを
混合した顔料組成物および水性顔料分散体について実施
例，比較例を挙げて説明する。例中「部」，「％」とは
それぞれ「重量部」，「重量％」を示す。また，実施例
の表中に示す顔料の凝集状態は得られた水性顔料分散体
を例中に示したビヒクルで希釈したときの状態を150倍
の光学顕微鏡で観察し,5段階で表示した。すなわち１は
凝集が無く，良好な状態で５は凝集が著しい状態を表わ
す。 Next, a pigment composition and an aqueous pigment dispersion prepared by mixing the compound of the general formula [I] obtained in Production Example with a pigment will be described with reference to Examples and Comparative Examples. In the examples, "part" and "%" mean "part by weight" and "% by weight", respectively. In addition, the aggregation state of the pigments shown in the tables of Examples was observed by an optical microscope with a magnification of 150 when the obtained aqueous pigment dispersion was diluted with the vehicle shown in the Examples, and displayed in 5 stages. That is, 1 represents no aggregation and 5 represents a good state, and 5 represents significant aggregation.
実施例 １ C.I.Pigment Blue 15 20部を含む水ペースト化合物
（ａ）２部を含む水ペーストおよび含有する水の合計が
68部になるように水を加えて水性用顔料組成物の懸濁液
を得る。次いで分散剤としてエマルゲンＡ−60（花王KK
製非イオン性界面活性剤）５部および乾燥防止剤として
エチレングリコール５部を加えてミキサーで3000rpm,1
時間撹拌後，サンドミルで粗大粒子が10μｍ以下になる
まで分散し，流動性の良好な水性顔料分散体を得た。こ
の分散体１部を酸化デンプンMS＃3600（日本食品化工KK
製）の10％水溶液100部に添加し，ミキサーで500rpm,5
分間撹拌して顕微鏡観察すると顔料の凝集は見られなか
った。Example 1 Water Paste Containing 20 Parts of CIPigment Blue 15 Water paste containing 2 parts of the compound (a) and water contained therein were
Water is added to 68 parts to obtain a suspension of the aqueous pigment composition. Then, as a dispersant, Emulgen A-60 (Kao KK
5 parts of non-ionic surfactant made by the manufacturer) and 5 parts of ethylene glycol as an anti-drying agent are added to the mixer at 3000 rpm, 1
After stirring for an hour, a sand mill was used to disperse coarse particles until the particle size became 10 μm or less, to obtain an aqueous pigment dispersion having good fluidity. 1 part of this dispersion is oxidized starch MS # 3600 (Nippon Shokuhin Kako KK
Manufactured by K.K.) and added to 100 parts of 10% aqueous solution, and mixed with a mixer at 500 rpm, 5
When agitated for 1 minute and observed under a microscope, no aggregation of pigment was observed.
さらにミキサーで5000rpm,20分間撹拌しても顔料の凝集
は見られなかった。Furthermore, no agglomeration of the pigment was observed even after stirring with a mixer at 5000 rpm for 20 minutes.
比 較 例 実施例１で化合物（ａ）を加えずに同様の操作を行うと
明らかに顔料の凝集が観察され，とくに強い撹拌のとき
に凝集が著しかった。Comparative Example When the same operation as in Example 1 was carried out without adding the compound (a), the aggregation of the pigment was clearly observed, and the aggregation was remarkable especially under strong stirring.
実施例 ２〜16 各種の顔料と製造例で示した各種の化合物を用いて実施
例１と同様の方法で水性顔料分散体を調整し，酸化でん
ぷん水溶液に添加したときの顔料の凝集状態の結果を表
２に示すが化合物を加えない場合と比較していずれも良
好だった。（但し，無機顔料の場合は50部を使用。） 次に本発明の水性用顔料組成物を用いて水性顔料分散体
を調整するにあたり，界面活性剤や水溶性樹脂などの分
散剤を加えない場合の説明をする。Examples 2 to 16 Aqueous pigment dispersions were prepared in the same manner as in Example 1 by using various pigments and various compounds shown in Production Examples, and the results of pigment aggregation state when added to an oxidized starch aqueous solution were obtained. Is shown in Table 2 and is good in comparison with the case where no compound is added. (However, 50 parts are used for inorganic pigments.) Next, in the case of preparing an aqueous pigment dispersion using the aqueous pigment composition of the present invention, the case where a dispersant such as a surfactant or a water-soluble resin is not added will be described.
実施例 17 C.I.Pigment Blue 15 20部を含む水ペースト化合物
（ａ）４部を含む水ペーストおよび含有する水の合計が
71部になるように水を加えて水性用顔料組成物の懸濁液
を得る。次いでエチレングリコール５部を加えてミキサ
ーで3000rpm,1時間撹拌後，サンドミルで粗大粒子が10
μｍ以下になるまで分散し，流動性の良好な水性顔料分
散体を得た。さらに実施例１と同様にビヒクルに添加し
た後に顕微鏡観察すると顔料の凝集な見られなかった。Example 17 CIPigment Blue 15 Water Paste Containing 20 Parts The total amount of water paste containing 4 parts of the compound (a) and water contained therein was
Water is added to make 71 parts to obtain a suspension of the aqueous pigment composition. Next, add 5 parts of ethylene glycol and stir at 3000 rpm for 1 hour with a mixer.
Dispersion was carried out until the particle size became not more than μm to obtain an aqueous pigment dispersion having good fluidity. Furthermore, as in Example 1, when the mixture was added to the vehicle and then observed under a microscope, no aggregation of pigment was observed.
比 較 例 実施例17で化合物の代りに分散剤としてエマルゲン911
（花王KK製，非イオン界面活性剤）８部を加えて同様の
操作を行うと明らかに顔料の凝集が観察された。Comparative Example Emulgen 911 as a dispersant instead of the compound in Example 17
When 8 parts (manufactured by Kao KK, nonionic surfactant) were added and the same operation was carried out, aggregation of the pigment was clearly observed.
実施例 18〜29 各種の顔料と製造例で示した各種の化合物を用いて実施
例17と同様の方法で顔料の凝集状態を観察すると表３に
示したように化合物の代りにエマルゲン911 ８部を加
えた場合（比較例）と比較していずれも顔料の凝集が少
なかった。Examples 18 to 29 When various pigments and various compounds shown in the production examples were used and the aggregation state of the pigments was observed in the same manner as in Example 17, as shown in Table 3, 8 parts of Emulgen 911 instead of the compound was observed. In each case, the aggregation of the pigment was small as compared with the case of adding (Comparative Example).
〔発明の効果〕 本発明の顔料組成物を用いることにより，従来になく，
流動性の良好な水性顔料分散体が得られ，この分散体を
種々の用途に応じたビヒクルに添加したときに顔料の凝
集がほとんど起こらなかった。さらに本発明の顔料組成
物を用いると，従来は水性顔料分散体の必須成分であっ
た界面活性剤や水溶性樹脂などの分散剤の添加は必ずし
も必要とせず，添加しなくても充分に効果があることが
確認された。 [Effects of the Invention] By using the pigment composition of the present invention,
An aqueous pigment dispersion having good fluidity was obtained, and when the dispersion was added to a vehicle according to various applications, pigment aggregation hardly occurred. Furthermore, when the pigment composition of the present invention is used, it is not always necessary to add a dispersant such as a surfactant or a water-soluble resin, which has conventionally been an essential component of an aqueous pigment dispersion, and it is possible to obtain a sufficient effect even if it is not added. It was confirmed that there is.
Claims (2)
合物0.3〜50重量部からなることを特徴とする顔料組成
物。 一般式〔Ｉ〕 Ｐ〔Ｘ−NR（CH2CHR′−Ｏ−）mH〕ｎ （但し，一般式中,Pは有機色素残基，アントラキノン残
基またはアクリドン残基,Xは−SO2−，−CO−，−CH2−
または−CH2NHCOCH2−,Rは水素原子，アルキル基または
（CH2CHR′−Ｏ−）lH,R′は水素原子またはメチル基,n
は１〜３の整数,mとｌはそれぞれ２〜100の整数を表わ
す。）1. A pigment composition comprising 100 parts by weight of a pigment and 0.3 to 50 parts by weight of a compound of the following general formula [I]. Formula (I) P [X-NR (CH 2 CHR'- O-) m H ] n (where, in the general formula, P is an organic pigment residue, anthraquinone residue, or acridone residue, X is -SO 2 −, −CO−, −CH 2 −
Or -CH 2 NHCOCH 2 -, R is a hydrogen atom, an alkyl group or (CH 2 CHR'-O-) lH , R ' is a hydrogen atom or a methyl radical, n
Is an integer of 1 to 3, m and l are integers of 2 to 100, respectively. )
ントラキノン系，キナクリドン系，ジオキサジン系，ア
ントラピリジン系，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，ペリレン系および
チオインジゴ系から選ばれる特許請求の範囲第１項記載
の顔料組成物。2. The organic dye is selected from phthalocyanine type, azo type, anthraquinone type, quinacridone type, dioxazine type, anthrapyridine type, ansanthrone type, indanthrone type, flavanthrone type, perinone type, perylene type and thioindigo type. The pigment composition according to claim 1, which is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62099121A JPH0778180B2 (en) | 1987-04-22 | 1987-04-22 | Pigment composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62099121A JPH0778180B2 (en) | 1987-04-22 | 1987-04-22 | Pigment composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63264674A JPS63264674A (en) | 1988-11-01 |
| JPH0778180B2 true JPH0778180B2 (en) | 1995-08-23 |
Family
ID=14238944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62099121A Expired - Fee Related JPH0778180B2 (en) | 1987-04-22 | 1987-04-22 | Pigment composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0778180B2 (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68922470T2 (en) * | 1988-11-26 | 1995-09-07 | Toppan Printing Co Ltd | Color filter for a multi-color liquid crystal display panel. |
| US5177200A (en) * | 1989-05-19 | 1993-01-05 | Milliken Research Corporation | Poly(oxyalkylene) modified phthalocyanine colorants |
| DE69121436T2 (en) * | 1990-03-09 | 1997-01-09 | Milliken Res Corp | Organic materials bearing sulfonamido-bonded poly (oxyalkylene) groups and their production |
| US5240464A (en) * | 1990-03-09 | 1993-08-31 | Milliken Research Corporation | Organic materials having sulfonamido linked poly(oxyalkylene) moieties and their preparation |
| US6060598A (en) * | 1990-05-15 | 2000-05-09 | Hyperion, Inc. | Fluorescence immunoassays using fluorescent dyes free of aggregation and serum binding |
| US5880287A (en) * | 1990-05-15 | 1999-03-09 | Hyperion, Inc. | Polyoxyhydrocarbyl related products and methods for fluorescence assays |
| US5403928A (en) * | 1990-05-15 | 1995-04-04 | Diatron Corporation | Fluorescent marker components and fluorescent probes |
| US5919922A (en) * | 1990-05-15 | 1999-07-06 | Hyperion, Inc. | Fluorescent dyes free of aggregation and serum binding |
| US5606045A (en) * | 1990-05-15 | 1997-02-25 | Diatron Corporation | Nucleic acid probes and methods |
| US6022944A (en) | 1990-09-05 | 2000-02-08 | Milliken & Company | Anthraquinone and condensed anthraquinone colorants having sulfonamide linked poly(oxyalkylene) moieties and their preparation |
| US5429841A (en) * | 1993-06-25 | 1995-07-04 | Milliken Research Corporation | Printing ink emulsion with poly(oxyalkylene) substituted colorant |
| US5532346A (en) * | 1994-10-21 | 1996-07-02 | Milliken Research Corporation | Hydroxynaphthalenecarboxylic acid compounds and azo colorants made therefrom |
| JP2007009096A (en) * | 2005-07-01 | 2007-01-18 | Toyo Ink Mfg Co Ltd | Pigment composition and pigment dispersion using the same |
| KR101639701B1 (en) | 2009-08-27 | 2016-07-14 | 후지필름 가부시키가이샤 | Dichlorodiketopyrrolopyrrole pigment, coloring material dispersion containing the pigment, and process for production of the coloring material dispersion |
| JP2011111577A (en) * | 2009-11-30 | 2011-06-09 | Pentel Corp | Aqueous paint composition |
| JP6184902B2 (en) * | 2014-05-30 | 2017-08-23 | 花王株式会社 | Carbon black dispersion |
| JP6946443B2 (en) | 2017-09-15 | 2021-10-06 | 富士フイルム株式会社 | Compositions, films, laminates, infrared transmission filters, solid-state image sensors and infrared sensors |
| EP3854821A4 (en) | 2018-09-20 | 2021-11-17 | FUJIFILM Corporation | Curable composition, cured film, infrared transmission filter, laminate, solid-state imaging element, sensor, and pattern formation method |
| CN114269556A (en) | 2019-08-29 | 2022-04-01 | 富士胶片株式会社 | Composition, film, near-infrared cut filter, pattern formation method, laminate, solid-state imaging element, infrared sensor, image display device, camera module, and compound |
| WO2022014635A1 (en) | 2020-07-15 | 2022-01-20 | 東洋インキＳｃホールディングス株式会社 | Pigment composition, coloring composition, paint, ink, ink set, printed article, and packaging material |
| WO2022131191A1 (en) | 2020-12-16 | 2022-06-23 | 富士フイルム株式会社 | Composition, membrane, optical filter, solid image pickup element, image display apparatus, and infrared ray sensor |
| WO2022130773A1 (en) | 2020-12-17 | 2022-06-23 | 富士フイルム株式会社 | Composition, film, optical filter, solid-state imaging element, image display device, and infrared sensor |
| JP7105024B1 (en) | 2021-08-03 | 2022-07-22 | 東洋インキＳｃホールディングス株式会社 | Pigment compositions, coloring compositions, paints, inks, ink sets, printed matter, and packaging materials |
-
1987
- 1987-04-22 JP JP62099121A patent/JPH0778180B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63264674A (en) | 1988-11-01 |
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