JP4629841B2 - Quinophthalone (CI Pigment Yellow 138) pigment and coloring composition containing the pigment - Google Patents
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Description
【０００１】
【発明の属する技術分野】
本発明は、透明性が高く、冴え、緑味鮮明な黄色を呈する特定のＸ線回折ピークを有するキノフタロン顔料及び該黄色顔料を着色剤とするカラーフィルター用や画像記録用に好適な着色組成物に関し、例えば、プラスチック、塗料、印刷インキ、捺染等の従来一般に顔料が使用されている用途だけではなく、電子トナー、熱転写インキ、特にカラーフィルター用顔料分散液や油性及び水性インクジェット用インキの製造に適した顔料に関するものである。更に詳しくは、特に、耐熱性、耐光性、耐溶剤性とともに透明性が高く、冴え、鮮明な黄色顔料が求められる画像記録用着色組成物等に好適なキノフタロン顔料に関するものである。
【０００２】
【従来の技術】
従来、液晶カラーディスプレー、撮像素子などの製造に使用されるカラーフィルターは、感光性樹脂液中に赤色（Ｒ）、緑色（Ｇ）及び青色（Ｂ）の三色の顔料をそれぞれ分散させたカラーフィルター用顔料分散液をスピンコート法、電着法、印刷法等によりカラーフィルター用基板に塗布して着色皮膜を形成後、フォトマスクを介して、着色皮膜を露光現像して着色皮膜をパターン化し、所望の画素を形成させる方法で主に形成される。
【０００３】
カラーフィルター用顔料分散液の製造に使用される主な顔料として、緑色はフタロシアニングリーン、例えば、C.I. Pigment green（以下P.G.と称す）３６、赤色はアントラキノン系レッド、例えば、C.I. Pigment red（以下P.R.と称す）１７７が一般的に用いられる。しかしながら、これらの顔料の色相と液晶ディスプレーに要求される色特性に差があり、いずれの色においても黄色顔料が補色として併用される。
【０００４】
カラーフィルター用に使用される顔料としては、耐熱性、耐光性、耐溶剤性、透明性等に優れた顔料が求められるが、黄色顔料の多くはアゾ基を有しており、比較的耐熱性、耐光性、耐溶剤性が悪い。
上記の理由のため、カラーフィルター用に使用する黄色顔料は、高級顔料と呼ばれるもの、例えば、イソインドリン構造を有するもの、イソインドリノン構造を有するもの、アゾ金属錯体、キノフタロン構造を有するもの、例えば、Pigmen-t Yellow 138 （以下では P.Y.138と称す）等の中から選択される。
又、最近、ＯＡ用プリンターにインクジェット方式の印刷機が急速に普及し始めている。一般にフルカラーのインクジェット方式の印刷機に使用されるインキには、黄色（Ｙ）、マゼンタ色（Ｍ）、シアン色（Ｃ）、及び黒（Ｋ）の四色の染料もしくは顔料が使用される。
【０００５】
インクジェット用インキ用の色材には、透明性が高く、冴え、鮮明なものが求められる。そのため、ＯＡ用プリンターに使用される色材は、ほとんど染料が用いられている。
しかし、インクジェット方式の印刷機は、ＯＡ用プリンターだけではなく、屋内外に展示されるポスターや建材等用の印刷等の工業分野にも幅広く応用されるようになった。そのため、屋外で使用するポスターや建材等では、従来から使用されている染料では、すぐに色飛びする等の原因になることから、耐候性等の物性に優れた顔料が要求されている。
【０００６】
【発明が解決しようとする課題】
下記の化学構造を有するキノフタロン顔料 P.Y.138は、耐熱性、耐候性、耐溶剤性、耐薬品性等の堅牢性に優れ、カラーフィルターやインクジェット用インキに要求される物性を充分満たす顔料である。
しかし、機械的に粉砕した粗顔料を有機液体で処理して顔料化された従来のキノフタロン顔料（P.Y.138 ）は、透明性、冴え及び鮮明性が劣るためにカラーフィルター用インキやインクジェット用インキへの応用が困難であり、改善が要望されている。
【０００７】
従って、本発明の目的は、透明性、冴え及び鮮明性に優れ、カラーフィルター用インキやインクジェット用インキへの応用が可能なキノフタロン顔料（P.Y.138)を提供することである。
本発明者らは透明性、冴え、鮮明性を改良すべくキノフタロン顔料（P.Y.138 ）を微細化する方法を種々検討した結果、微細化の条件によって結晶型が、ＣｕＫα線のＸ線回折の結果、ブラッグ角（２θ±０．２°）８．４、１２．７、２０．３、２２．０、２３．７、２４．８、２５．６、２８．３、及び３２．７度の位置に明確な回折ピークを有するもの（本発明ではこれをＡ型キノフタロン顔料と称する。）（図１参照）と、ブラッグ角（２θ±０．２°）９．４、１２．２、１２．８、１４．６、１９．８、２２．５、２５．７、２６．１、２７．９、２８．７及び３１．１度の位置に明確な回折ピークを有するもの（本発明ではこれをＢ型キノフタロン顔料と称する。）（図２参照）等のいくつかの結晶型を有するもの（同質多型）が得られることを見出した。
【０００９】
そして、Ａ型及びＢ型キノフタロン顔料の特性を比較したところ、Ａ型キノフタロン顔料（P.Y.138 ）は、Ｂ型キノフタロン顔料と比較して透明性が劣り、カラーフィルター用顔料分散液や油性及び水性インクジェット用インキへの応用は困難であるが、Ｂ型キノフタロン顔料は著しく透明性が高く、冴え及び鮮明性に優れ、上記の用途で充分に使用できることを見出し、本発明に至った。
【００１０】
【課題を解決するための手段】
上記の目的は、以下の本発明によって達成される。即ち、本発明は、粗製キノフタロン顔料（Ｃ．Ｉ．Ｐｉｇｍｅｎｔ Ｙｅｌｌｏｗ １３８）を少なくとも９０〜１００℃で摩砕して顔料化されてなる、そのブラッグ角（２θ±０．２°）９．４、１２．２、１２．８、１４．６、１９．８、２２．５、２５．７、２６．１、２７．９、２８．７および３１．１度にＸ線（ＣｕＫα線）回折ピークを有し、ＢＥＴ比表面積が７０〜１５０ｍ2／ｇの範囲であり、平均一次粒子径が０．０４μｍ以下であることを特徴とするＣ．Ｉ．Ｐｉｇｍｅｎｔ Ｙｅｌｌｏｗ １３８及び上記の顔料を着色剤として少なくとも含むことを特徴とする着色組成物である。
【００１１】
【発明の実施の形態】
次に発明の実施の形態を挙げて、本発明を更に詳細に説明する。
本発明のキノフタロン顔料は、前記の化学構造を有するC.I.Pigment Yellow 138と表示されるそれ自体公知の顔料であり、前記のブラッグ角に明確なＸ線（ＣｕＫα線の）回折ピークを示す結晶型のＢ型キノフタロン顔料である。キノフタロン顔料の合成方法は、従来公知の合成方法がいずれも使用でき、特に制限されない。
本発明のＢ型キノフタロン顔料は、公知の方法で合成したキノフタロン顔料を、制御された条件下での顔料化の工程を経ることによって得ることができる。更に、一次粒子の平均粒子径を０．０４μｍ以下、好ましくは０．０３μｍ以下、又、ＢＥＴ法（Ｎ2吸着）による比表面積を７０〜１５０ｍ2／ｇの範囲に調整することによって、著しく透明性が高く、冴え、鮮明性に優れたカラーフィルター用顔料分散液やインクジェット用インキ等の製造に使用することが可能となる。
【００１２】
本発明のＢ型キノフタロン顔料（P.Y.138 ）は、粗製キノフタロン顔料を、例えば、機械的エネルギーにより乾燥状態で粉砕し、粉砕物を湿式摩砕する等の方法で得ることができる。機械的エネルギーにより粉砕化する方法で使用される装置としては、ボールミル、アトライター、振動ミル、サンドミル等の衝突粉砕によるものや、ニーダー、バンバリーミキサー、ロールミル等の剪断力により粉砕化するものがあるが、これらに限定されるものではない。分散メディアの使用は必ずしも必要ではないが、例えば、ガラスビーズ、スチールボール、ジルコニアボール、チタニアボール、アルミナボール、スチールロッド等の分散メディアを使用することができる。又、必要に応じ、食塩、無水芒硝、硫酸アルミニウム等の磨砕助剤を使用することができる。湿式摩砕は、従来公知の方法に従えばよく特に限定されない。上記の衝突粉砕による装置、溶剤としては、例えば、ジエチレングリコール、ポリエチレングリコール等の水溶性有機溶剤が、又は摩砕助剤としては上記のものが用いられる。湿式摩砕の温度は、好ましくは８０℃以上、更に好ましくは９０〜１００℃である。
【００１３】
本発明のＢ型キノフタロン顔料（P.Y.138)に易分散性等の物性を付与するために、該顔料を顔料誘導体や高分子分散剤等の従来公知の表面処理剤、分散剤、または界面活性剤等で処理することができる。
このようにして得られたＢ型キノフタロン顔料は、透明性が高く、冴え、色相の緑味鮮明性を有し、又、耐熱性、耐光性、耐溶剤性等の諸堅牢性に優れた性質を示す。
【００１４】
本発明の着色組成物は、Ｂ型キノフタロン顔料を着色剤として少なくとも含有するものであり、その用途に応じて、それぞれの用途で従来から使用される各種成分を含有することができる。例えば、着色組成物を画像記録用着色剤として使用する場合には、例えば、熱可塑性重合体樹脂やワックス類等の樹脂が用いられる。これらの樹脂は、画像記録用着色剤が固体の形態で使用される場合には分散媒体であり、液体の形態で使用される場合には、顔料の分散剤として機能するものである。又、画像記録用着色剤が、そのまま或いはこれを用いた画像記録剤として使用される時には、顔料の固着剤として作用する。
【００１５】
このような目的で使用される樹脂としては、カラーフィルター用顔料分散液、油性及び水性インクジェットインク、熱転写インクフィルム、電子トナー等の画像記録用着色剤に使用されている従来公知の皮膜形成樹脂等が使用でき、特に限定されない。又、液体媒体として有機溶剤、水、有機溶剤と水との混合物を使用することができる。上記の各用途に合わせて、必要に応じて従来公知の添加剤、例えば、分散助剤、電荷調製剤、塗膜調整剤等を使用することができる。
【００１６】
画像記録用着色剤やカラーフィルター用顔料分散液の製造において、上記皮膜形成樹脂に対する本発明のＢ型キノフタロン顔料の使用割合は、通常、皮膜形成樹脂１００重量部に対し、５〜５００重量部の範囲が好ましい。又、媒体やその他の添加剤を含む全画像記録用着色剤や全カラーフィルター用顔料分散液における顔料の含有量は、通常１〜３０重量％程度である。更に詳しくは、カラーフィルター用顔料分散液として使用される場合、１〜３０重量％程度、好ましくは２〜２０重量％であり、インクジェット記録用インキとして使用される場合、３〜２０重量％程度、好ましくは５〜１０重量％であり、又、熱転写インクフィルムとして使用される場合、４〜１５重量％程度、好ましくは６〜１０重量％であり、各々使用する目的に応じて最も好ましい含有量で使用される。
【００１７】
画像記録用着色剤の製造方法としては、湿式の媒体分散法と乾式の加熱混練分散法等があるが、製造方法は限定されない。
湿式の媒体分散法とは、適当な皮膜形成樹脂を含む有機溶剤溶液または水溶液中に顔料を添加してプレミキシングし、その後分散処理を行う。通常、アトライター、サンドミル、ダイノミル等の装置を用いるが、これらの分散装置に限定されるものではない。
又、乾式の加熱混練分散法では、通常、二本ロール、三本ロール、加熱ニーダー、加圧加熱ニーダー、一軸押出機、二軸押出機等の混練分散機を使用して樹脂を溶融して顔料を混練分散させる。
【００１８】
上記のように構成された本発明により、Ｂ型キノフタロン顔料組成物をカラーフィルター用顔料分散液、油性及び水性インクジェット等の画像記録用着色剤組成物として使用することにより、耐熱性、耐候性、耐溶剤性、耐薬品製等の堅牢性に優れ、且つ透明性が高く、冴え、緑味鮮明な黄色画像やフィルターを形成することができる。
尚、本発明のＢ型キノフタロン顔料組成物は、上記画像記録用着色剤組成物だけではなくプラスチック、塗料、印刷インキ、捺染等の従来一般用途にも使用できることは勿論のことである。
【００１９】
【実施例】
以下、実施例及び比較例を挙げて本発明を具体的に説明する。尚、文中、部または％とあるのは特に断りのない限り重量基準である。又、顔料の平均一次粒子径は、透過型電子顕微鏡を用いて測定した。
【００２０】
実施例１
公知の方法で合成され、機械的に粉砕された粗製のキノフタロン顔料（P.Y.138 ）１００部と食塩１０００部、及びジエチレングリコール１２０部をニーダー中で内容温度を９０〜１００℃に保って１５時間摩砕を行った。
得られた内容物を２％の希硫酸水溶液中で加熱処理をし、濾過、水洗、乾燥することによって平均一次粒子径０．０２μｍ、ＢＥＴ比表面積８８ｍ2／ｇのＢ型キノフタロン（P.Y.138 ）顔料を得た。ＣｕＫα線のＸ線回折図を図１に示す。
【００２１】
比較例１
ニーダー中の内容温度を３０〜４０℃に保って１５時間摩砕を行った以外は、実施例１と同様にして平均一次粒子径０．０３μｍ、ＢＥＴ比表面積８０ｍ2／ｇのＡ型キノフタロン（P.Y.138 ）顔料を得た。ＣｕＫα線のＸ線回折図を図２に示す。
【００２２】
比較例２
公知の方法で合成され、機械的に粉砕された粗製のキノフタロン顔料（P.Y.138 ）１００部と食塩３００部、及びジエチレングリコール９０部をニーダー中で内容温度を９０〜１００℃に保って１５時間摩砕を行った。
得られた内容物を２％の希硫酸水溶液中で加熱処理をし、濾過、水洗、乾燥することによって平均一次粒子径０．２μｍ、ＢＥＴ比表面積４０ｍ2／ｇのＢ型キノフタロン（P.Y.138 ）顔料を得た。ＣｕＫα線のＸ線回折図は図１と同じであった。
【００２３】
実施例２、比較例３〜４
以下に、実施例１及び比較例１〜２で得られたでＢ型及びＡ型キノフタロン顔料をそれぞれ着色剤とするカラーフィルター用着色組成物について例示する。
表１に示す配合処方で各配合物を攪拌機（ディスパー）で攪拌混合し、ついでこの混合物を小型ビーズミルに入れて分散処理を施してカラーフィルター用顔料分散液を調製し、これを用いてカラーフィルターの性能を評価した。
【００２４】
調製された分散液をそれぞれスピンコーターにてガラス基板上に塗布し、プリベークした。選られた各塗布パネルをカラコムＣ（大日精化工業社製：ＣＣＭ（コンピューターカラーマッチング）＆色彩管理システム）で測色したところ表２に示す結果が得られた。また、分光光度計で測定した透過率曲線を図３に示す。
【００２６】
プリベーク膜で透過率カーブ（図３参照）を比較すると、実施例２の黄色分散液は、比較例３、４の分散液と比較して４００〜４６０ｎｍの短波領域では吸収が強く、また、５００ｎｍ以上の領域では高透過率であり、優位性が認められた。
【００２８】
実施例３
実施例１で得られた顔料組成物のプレスケーキを用い、表３に示す配合処方の水性顔料分散液を調製し、超遠心分離機で分散し得なかった顔料粗粒子を除去し、インクジェット用水性イエロー分散液を得た。このインキを用いてピエゾ振動子を有するオンデマンド型のインクジェットプリンターで画像情報を印刷し、鮮明な黄色画像を得た。
【００２９】
又、マゼンタ色としてC.I.Pigment Red 122 、シアン色として C.I.Pigment Bule 15:3、ブラック色としてC.I.Pigment Black 7を用い、上記と同様の配合処方で、各顔料を２００ｎｍ以下に分散させた顔料分散液を調製した。
これらの３色のカラー分散液と上記で得たイエロー分散液を用い四色フルカラー印刷を行い、鮮明なフルカラー画像を得た。又、ＯＨＰスクリーンに鮮明なフルカラー映像を映す画像を得た。
【００３１】
【発明の効果】
以上の本発明によれば、透明性、冴え及び鮮明性に優れたカラーフィルター用インキや画像記録用着色組成物の顔料として、又、塗料、印刷インキ、プラスチック等の着色用顔料として使用可能なＢ型キノフタロン（Ｃ．Ｉ．Ｐｉｇｍｅｎｔ Ｙｅｌｌｏｗ １３８）顔料組成物が提供される。
【図面の簡単な説明】
【図１】 Ｂ型キノフタロン顔料組成物のＸ線回折図。
【図２】 Ａ型キノフタロン顔料組成物のＸ線回折図。
【図３】 実施例２及び比較例３〜４のカラーフィルター用顔料分散液でガラス基板上に形成されたプリベーク皮膜の透過率曲線。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a quinophthalone pigment having a specific X-ray diffraction peak that has high transparency, a clear, greenish and clear yellow color, and a coloring composition suitable for color filters and image recordings using the yellow pigment as a colorant. For example, not only the use of conventional pigments such as plastics, paints, printing inks and textile printing, but also the production of electronic toners, thermal transfer inks, especially pigment dispersions for color filters and oil-based and water-based inkjet inks. It relates to suitable pigments. More particularly, the present invention relates to a quinophthalone pigment that is suitable for a coloring composition for image recording and the like that requires a clear, clear yellow pigment that has high heat resistance, light resistance, and solvent resistance.
[0002]
[Prior art]
Conventionally, color filters used for manufacturing liquid crystal color displays, image sensors, etc. are colors in which three color pigments of red (R), green (G), and blue (B) are dispersed in a photosensitive resin liquid, respectively. After applying the pigment dispersion for the filter to the color filter substrate by spin coating, electrodeposition, printing, etc. to form a colored film, the colored film is exposed and developed through a photomask to pattern the colored film. The pixel is mainly formed by a method of forming a desired pixel.
[0003]
As main pigments used in the production of pigment dispersions for color filters, green is phthalocyanine green, such as CI Pigment green (hereinafter referred to as PG) 36, and red is an anthraquinone red, such as CI Pigment red (hereinafter referred to as PR). 177) is commonly used. However, there is a difference between the hue of these pigments and the color characteristics required for the liquid crystal display, and a yellow pigment is used as a complementary color in any color.
[0004]
As pigments used for color filters, pigments excellent in heat resistance, light resistance, solvent resistance, transparency, etc. are required, but most yellow pigments have an azo group and are relatively heat resistant. Poor light resistance and solvent resistance.
For the above reasons, yellow pigments used for color filters are called high-grade pigments, for example, those having an isoindoline structure, those having an isoindolinone structure, those having an azo metal complex, a quinophthalone structure, for example, Pigmen-t Yellow 138 (hereinafter referred to as PY138).
Recently, inkjet printers have begun to spread rapidly in OA printers. In general, four colors of dyes or pigments of yellow (Y), magenta (M), cyan (C), and black (K) are used for inks used in full-color inkjet printers.
[0005]
Color materials for ink jet inks are required to be highly transparent, clear and clear. For this reason, dyes are mostly used for color materials used in OA printers.
However, inkjet printers have been widely applied not only to OA printers but also to industrial fields such as printing for posters and building materials displayed indoors and outdoors. For this reason, pigments having excellent physical properties such as weather resistance are required for posters and building materials used outdoors, because dyes that have been used in the past cause color skipping.
[0006]
[Problems to be solved by the invention]
The quinophthalone pigment PY138 having the following chemical structure is a pigment that is excellent in fastness such as heat resistance, weather resistance, solvent resistance, chemical resistance and the like and sufficiently satisfies the physical properties required for color filters and inks for inkjet.
However, the conventional quinophthalone pigment (PY138), which is obtained by pigmenting mechanically pulverized crude pigment with an organic liquid, is inferior in transparency, texture and vividness. Application is difficult and improvement is desired.
[0007]
Accordingly, an object of the present invention is to provide a quinophthalone pigment (PY138) which is excellent in transparency, texture and sharpness and can be applied to color filter inks and inkjet inks.
As a result of examining various methods for refining the quinophthalone pigment (PY138) in order to improve transparency, texture, and sharpness, the present inventors have determined that the crystal form is the result of X-ray diffraction of CuKα rays depending on the refining conditions. Bragg angle (2θ ± 0.2 °) at 8.4, 12.7, 20.3, 22.0, 23.7, 24.8, 25.6, 28.3, and 32.7 degrees Those having clear diffraction peaks (in the present invention, these are referred to as A-type quinophthalone pigments) (see FIG. 1), Bragg angles (2θ ± 0.2 °) 9.4, 12.2, 12.8, 14.6, 19.8, 22.5, 25.7, 26.1, 27.9, 28.7, and those having clear diffraction peaks at 31.1 degrees (in the present invention, this is B-type) (Referred to as quinophthalone pigment) (see FIG. 2) and other crystalline forms (same polymorphs) are obtained. It found Rukoto.
[0009]
When the characteristics of the A-type and B-type quinophthalone pigments were compared, the A-type quinophthalone pigment (PY138) was inferior in transparency to the B-type quinophthalone pigment, and the pigment dispersion for color filters and oil-based and water-based inkjets were used. Although application to ink is difficult, the B-type quinophthalone pigment was found to be remarkably high in transparency, excellent in sharpness and sharpness, and sufficiently used in the above-mentioned applications, leading to the present invention.
[0010]
[Means for Solving the Problems]
The above object is achieved by the present invention described below. That is, the present invention is a pigment obtained by grinding a crude quinophthalone pigment (CI Pigment Yellow 138) at least at 90 to 100 ° C., its Bragg angle (2θ ± 0.2 °) 9.4, X-ray (CuKα ray) diffraction peaks at 12.2, 12.8, 14.6, 19.8, 22.5, 25.7, 26.1, 27.9, 28.7 and 31.1 degrees Having a BET specific surface area of 70 to 150 m 2 / g and an average primary particle size of 0.04 μm or less. I. Pigment Yellow 138 and the above-mentioned pigment at least as a coloring agent, It is a coloring composition characterized by the above-mentioned.
[0011]
DETAILED DESCRIPTION OF THE INVENTION
Next, the present invention will be described in more detail with reference to embodiments of the invention.
The quinophthalone pigment of the present invention is a pigment known per se, which is expressed as CIPigment Yellow 138 having the above-mentioned chemical structure, and has a crystal type B showing a clear X-ray (CuKα-ray) diffraction peak at the Bragg angle. Type quinophthalone pigment. As a method for synthesizing the quinophthalone pigment, any conventionally known synthesis method can be used and is not particularly limited.
The B-type quinophthalone pigment of the present invention can be obtained by subjecting a quinophthalone pigment synthesized by a known method to a pigmentation step under controlled conditions. Furthermore, the average particle diameter of primary particles is 0.04 μm or less, preferably 0.03 μm or less, and the specific surface area by BET method (N 2 adsorption) is adjusted to be in the range of 70 to 150 m 2 / g. It can be used for the production of pigment dispersions for color filters, ink jet inks, and the like that are high in properties and have excellent clarity and clarity.
[0012]
The B-type quinophthalone pigment (PY138) of the present invention can be obtained by, for example, a method in which a crude quinophthalone pigment is pulverized in a dry state by mechanical energy and the pulverized product is wet-ground. As an apparatus used in the method of pulverizing with mechanical energy, there are those by impact pulverization such as ball mill, attritor, vibration mill, sand mill, and those pulverized by shearing force such as kneader, Banbury mixer, roll mill, etc. However, it is not limited to these. Although it is not always necessary to use a dispersion medium, for example, dispersion media such as glass beads, steel balls, zirconia balls, titania balls, alumina balls, steel rods, and the like can be used. If necessary, grinding aids such as salt, anhydrous sodium sulfate, and aluminum sulfate can be used. The wet milling is not particularly limited as long as a conventionally known method is followed. As the apparatus and solvent for collision pulverization, for example, water-soluble organic solvents such as diethylene glycol and polyethylene glycol are used, and the above-mentioned ones are used as grinding aids. The wet milling temperature is preferably 80 ° C or higher, more preferably 90 to 100 ° C.
[0013]
In order to give the B-type quinophthalone pigment (PY138) of the present invention physical properties such as easy dispersibility, the pigment is treated with a conventionally known surface treatment agent such as a pigment derivative or a polymer dispersant, a dispersant, a surfactant, or the like. Can be processed.
The B-type quinophthalone pigment obtained in this way has high transparency, a clear appearance, green hue clarity, and excellent properties such as heat resistance, light resistance and solvent resistance. Indicates.
[0014]
The colored composition of the present invention contains at least a B-type quinophthalone pigment as a colorant, and can contain various components conventionally used in each application depending on the application. For example, when the coloring composition is used as a colorant for image recording, for example, resins such as thermoplastic polymer resins and waxes are used. These resins are dispersion media when the colorant for image recording is used in a solid form, and function as a dispersant for a pigment when used in a liquid form. Further, when the colorant for image recording is used as it is or as an image recording agent using the same, it acts as a pigment fixing agent.
[0015]
Examples of resins used for such purposes include pigment dispersions for color filters, oil-based and water-based inkjet inks, thermal transfer ink films, and conventionally known film-forming resins used for image recording colorants such as electronic toners. It can be used and is not particularly limited. Further, an organic solvent, water, or a mixture of an organic solvent and water can be used as the liquid medium. Conventionally known additives such as a dispersion aid, a charge adjusting agent, a coating film adjusting agent, and the like can be used according to each of the above-mentioned applications as necessary.
[0016]
In the production of a colorant for image recording and a pigment dispersion for color filters, the ratio of the B-type quinophthalone pigment of the present invention to the film-forming resin is usually 5 to 500 parts by weight with respect to 100 parts by weight of the film-forming resin. A range is preferred. Further, the content of the pigment in the colorant for all image recording including the medium and other additives and the pigment dispersion for all color filters is usually about 1 to 30% by weight. More specifically, when used as a pigment dispersion for a color filter, it is about 1 to 30% by weight, preferably 2 to 20% by weight. When used as an ink for inkjet recording, about 3 to 20% by weight, Preferably, it is 5 to 10% by weight, and when used as a thermal transfer ink film, it is about 4 to 15% by weight, preferably 6 to 10% by weight, and is used at the most preferable content depending on the purpose of use. Is done.
[0017]
Examples of the method for producing the colorant for image recording include a wet medium dispersion method and a dry heat kneading dispersion method, but the production method is not limited.
In the wet medium dispersion method, a pigment is added to an organic solvent solution or an aqueous solution containing an appropriate film-forming resin and premixed, and then a dispersion treatment is performed. Usually, an apparatus such as an attritor, a sand mill, or a dyno mill is used, but it is not limited to these dispersing apparatuses.
In the dry heating and kneading dispersion method, the resin is usually melted by using a kneading and dispersing machine such as a two-roll, three-roll, heating kneader, pressure heating kneader, single screw extruder, twin screw extruder or the like. The pigment is kneaded and dispersed.
[0018]
By using the B-type quinophthalone pigment composition as a color dispersion for color filters, oil-based and color recording compositions for water-based inkjet, etc. according to the present invention configured as described above, heat resistance, weather resistance, It is excellent in fastness such as solvent resistance and chemical resistance, and has high transparency, and can form a clear, greenish and clear yellow image or filter.
Of course, the B-type quinophthalone pigment composition of the present invention can be used not only for the above-mentioned colorant composition for image recording but also for conventional general uses such as plastics, paints, printing inks and textile printing.
[0019]
【Example】
Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples. In the text, “part” or “%” is based on weight unless otherwise specified. The average primary particle size of the pigment was measured using a transmission electron microscope.
[0020]
Example 1
100 parts of a crude quinophthalone pigment (PY138) synthesized by a known method and mechanically pulverized, 1000 parts of sodium chloride and 120 parts of diethylene glycol were ground in a kneader at a content temperature of 90 to 100 ° C. for 15 hours. went.
The obtained contents are heat-treated in a 2% dilute sulfuric acid aqueous solution, filtered, washed with water and dried to obtain a B-type quinophthalone (PY138) pigment having an average primary particle size of 0.02 μm and a BET specific surface area of 88 m 2 / g. Got. An X-ray diffraction diagram of CuKα rays is shown in FIG.
[0021]
Comparative Example 1
A-type quinophthalone having an average primary particle size of 0.03 μm and a BET specific surface area of 80 m 2 / g in the same manner as in Example 1 except that the content temperature in the kneader was kept at 30 to 40 ° C. for 15 hours. PY138) a pigment was obtained. An X-ray diffraction diagram of the CuKα ray is shown in FIG.
[0022]
Comparative Example 2
100 parts of a crude quinophthalone pigment (PY138) synthesized by a known method and mechanically pulverized, 300 parts of sodium chloride and 90 parts of diethylene glycol were milled for 15 hours while keeping the content temperature at 90-100 ° C. in a kneader. went.
B-type quinophthalone (PY138) pigment having an average primary particle size of 0.2 μm and a BET specific surface area of 40 m 2 / g is obtained by heat-treating the obtained contents in a 2% dilute sulfuric acid aqueous solution, filtering, washing and drying. Got. The X-ray diffraction pattern of CuKα ray was the same as FIG.
[0023]
Example 2, Comparative Examples 3-4
Below, the coloring composition for color filters which uses the B-type and A-type quinophthalone pigment obtained in Example 1 and Comparative Examples 1-2 as a coloring agent is illustrated, respectively.
Each composition is stirred and mixed with a stirrer (disper) according to the formulation shown in Table 1, and then this mixture is placed in a small bead mill to be dispersed to prepare a pigment dispersion for a color filter, which is used as a color filter. The performance of was evaluated.
[0024]
Each of the prepared dispersions was applied onto a glass substrate with a spin coater and prebaked. When each selected coating panel was measured with Caracom C (Daiichi Seika Kogyo Co., Ltd .: CCM (Computer Color Matching) & Color Management System), the results shown in Table 2 were obtained. Moreover, the transmittance curve measured with the spectrophotometer is shown in FIG.
[0026]
Comparing the transmittance curve (see FIG. 3) with the pre-baked film, the yellow dispersion liquid of Example 2 is more strongly absorbed in the short wave region of 400 to 460 nm than the dispersion liquids of Comparative Examples 3 and 4, and 500 nm. In the above region, the transmittance was high and superiority was recognized.
[0028]
Example 3
Using the press cake of the pigment composition obtained in Example 1, an aqueous pigment dispersion having the formulation shown in Table 3 was prepared, and the pigment coarse particles that could not be dispersed by the ultracentrifuge were removed, and the ink jet ink was used. An aqueous yellow dispersion was obtained. Using this ink, image information was printed by an on-demand type ink jet printer having a piezoelectric vibrator, and a clear yellow image was obtained.
[0029]
In addition, CIPigment Red 122 as a magenta color, CIPigment Bule 15: 3 as a cyan color, and CIPigment Black 7 as a black color were used, and a pigment dispersion was prepared by dispersing each pigment to 200 nm or less with the same formulation as above. .
Using these three color dispersions and the yellow dispersion obtained above, four-color full color printing was performed to obtain a clear full color image. In addition, an image showing a clear full-color image on an OHP screen was obtained.
[0031]
【The invention's effect】
According to the present invention as described above, it can be used as a pigment for color filter inks and color composition for image recording excellent in transparency, texture and clarity, and as a pigment for coloring paints, printing inks, plastics and the like. A B-type quinophthalone (CI Pigment Yellow 138) pigment composition is provided.
[Brief description of the drawings]
FIG. 1 is an X-ray diffraction pattern of a B-type quinophthalone pigment composition.
FIG. 2 is an X-ray diffraction pattern of an A-type quinophthalone pigment composition.
FIG. 3 is a transmittance curve of a pre-baked film formed on a glass substrate with the pigment dispersion for color filter of Example 2 and Comparative Examples 3-4.
Claims (4)
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| JP2000296917A JP4629841B2 (en) | 2000-09-28 | 2000-09-28 | Quinophthalone (CI Pigment Yellow 138) pigment and coloring composition containing the pigment |
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| JP2002212438A (en) * | 2001-01-16 | 2002-07-31 | Hitachi Chem Co Ltd | Green resin composition, photosensitive green resin composition, photosensitive liquid for formation of green image, and manufacturing methods of green-colored image and color filter |
| JP4469600B2 (en) * | 2003-12-26 | 2010-05-26 | 東洋インキ製造株式会社 | Coloring composition for color filter and color filter |
| US7060835B2 (en) * | 2003-12-31 | 2006-06-13 | Sun Chemical Corporation | Preparation of yellow pigment |
| EP1783182B1 (en) | 2004-10-22 | 2009-12-23 | Seiko Epson Corporation | Inkjet recording ink |
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| JPH11269420A (en) * | 1998-03-23 | 1999-10-05 | Toyo Ink Mfg Co Ltd | Method for treating pigment and ink jet recording fluid |
| JP2000136253A (en) * | 1998-08-28 | 2000-05-16 | Toray Ind Inc | Colored polymer thin film, color filter and liquid crystal display apparatus |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH11269420A (en) * | 1998-03-23 | 1999-10-05 | Toyo Ink Mfg Co Ltd | Method for treating pigment and ink jet recording fluid |
| JP2000136253A (en) * | 1998-08-28 | 2000-05-16 | Toray Ind Inc | Colored polymer thin film, color filter and liquid crystal display apparatus |
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