JPH09279052A - Production of isoindolinone pigment and optical element using the pigment - Google Patents
Production of isoindolinone pigment and optical element using the pigmentInfo
- Publication number
- JPH09279052A JPH09279052A JP8094097A JP9409796A JPH09279052A JP H09279052 A JPH09279052 A JP H09279052A JP 8094097 A JP8094097 A JP 8094097A JP 9409796 A JP9409796 A JP 9409796A JP H09279052 A JPH09279052 A JP H09279052A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- optical element
- isoindolinone
- water
- transmittance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Liquid Crystal (AREA)
- Optical Filters (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、光学素子、特に液
晶表示素子用カラーフィルター等に有用なイソインドリ
ノン系顔料の製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an isoindolinone pigment useful for an optical element, particularly a color filter for a liquid crystal display element.
【０００２】[0002]
【従来の技術】コンピュータやテレビ等では、ディスプ
レーの薄型化、省電力化を目的に液晶表示素子が広く用
いられている。液晶表示素子は、カラーフィルターと組
み合わせることにより、カラー化することができる。従
来、カラーフィルターの着色剤としては、主として染料
が用いられてきたが、耐光性等への要求品質が高まって
いることを背景に、顔料への移行が進行している。2. Description of the Related Art In computers, televisions and the like, liquid crystal display elements are widely used for the purpose of making displays thinner and saving power. The liquid crystal display element can be colored by combining with a color filter. Conventionally, a dye has been mainly used as a colorant for a color filter, but the shift to a pigment is progressing against the backdrop of the demand for high quality such as light resistance.
【０００３】カラーフィルターに用いられる顔料は、鮮
明であること、透明であること等に加え、カラーフィル
ター製造工程上の要請から、耐熱性に優れていることも
要求されている。カラーフィルターに求められる色特性
としては、ＮＴＳＣの３原色に近いこと等が挙げられる
が、現在、用いられている赤顔料および緑顔料には、単
独で３原色を再現できるものが無いため、多くの場合、
これらの顔料に黄顔料を添加し、調色されて、カラーフ
ィルター用途に使用されている。そのような用途に用い
られる黄色有機顔料としては、アゾレーキ顔料、不溶性
アゾ顔料、縮合アゾ顔料等のアゾ系黄色顔料、スレン系
顔料、フタロン系顔料、メチン系顔料、イソインドリノ
ン系顔料等の縮合多環系顔料、および金属錯体顔料等が
知られている。Pigments used for color filters are required to have excellent heat resistance in addition to being clear and transparent, and also due to requirements in the color filter manufacturing process. Color characteristics required for color filters include that they are close to the three primary colors of NTSC, but many red pigments and green pigments that are currently used cannot reproduce the three primary colors by themselves. in the case of,
A yellow pigment is added to these pigments to be toned and used for color filter applications. Examples of yellow organic pigments used for such purposes include condensation of azo yellow pigments such as azo lake pigments, insoluble azo pigments and condensed azo pigments, slene pigments, phthalone pigments, methine pigments and isoindolinone pigments. Polycyclic pigments, metal complex pigments and the like are known.
【０００４】これらの中でも、特に、イソインドリノン
系顔料は、耐熱性、耐候性に優れており、塗料、プラス
チック用途に広範に使用されている。Of these, isoindolinone pigments are particularly excellent in heat resistance and weather resistance, and are widely used for paints and plastics.
【０００５】[0005]
【発明が解決しようとする課題】しかしながら、従来の
方法で製造されたイソインドリノン系顔料は、一次粒子
径が大きく、該顔料を使用したカラーフィルターには、
透過率、色純度が低いという問題点があった。However, the isoindolinone pigment produced by the conventional method has a large primary particle size, and a color filter using the pigment is
There is a problem that the transmittance and the color purity are low.
【０００６】本発明が解決しようとする課題は、耐熱
性、耐候性だけでなく、カラーフィルターの如き光学素
子に用いた場合に、鮮明性、透明性に優れたイソインド
リノン系顔料を提供することにある。The problem to be solved by the present invention is to provide an isoindolinone pigment excellent not only in heat resistance and weather resistance but also in sharpness and transparency when used for optical elements such as color filters. Especially.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、カラーフ
ィルターの如き光学素子に用いるのに適したイソインド
リノン系顔料の顔料化方法について鋭意研究を重ねた結
果、イソインドリノン系顔料を硫酸に溶解し、次いで該
硫酸溶液を水中に加えて析出させる方法により製造され
たイソインドリノン系顔料が、カラーフィルターの如き
光学素子に用いた場合に優れた特性を示すことを見出
し、本発明を完成するに至った。Means for Solving the Problems The inventors of the present invention have conducted extensive studies on a method for pigmenting an isoindolinone pigment suitable for use in an optical element such as a color filter. It has been found that an isoindolinone-based pigment produced by a method of dissolving in sulfuric acid and then adding the sulfuric acid solution into water to cause precipitation exhibits excellent properties when used in an optical element such as a color filter, and the present invention. Has been completed.
【０００８】即ち、本発明は上記課題を解決するため
に、イソインドリノン系粗製顔料を硫酸に溶解し、次い
で該硫酸溶液を水中に加えて析出させることを特徴とす
るイソインドリノン系顔料の製造方法を提供する。[0008] That is, in order to solve the above-mentioned problems, the present invention is characterized in that a crude isoindolinone pigment is dissolved in sulfuric acid, and then the sulfuric acid solution is added to water to cause precipitation. A manufacturing method is provided.
【０００９】[0009]
【発明の実施の形態】本発明で用いられるイソインドリ
ノン系顔料としては、硫酸に溶解し、かつ硫酸溶液中で
顕著な分解を起こさないものであれば、任意のものを用
いることができる。なかでも、光学素子として要求され
る色相、耐熱性等を考慮し、該イソインドリノン顔料を
用いて調色したカラーフィルターの色相がＮＴＳＣの三
原色に近い点で、Ｃ．Ｉ．ピグメント イエロー １１
０が特に好ましい。As the isoindolinone pigment used in the present invention, any pigment may be used as long as it is soluble in sulfuric acid and does not cause significant decomposition in a sulfuric acid solution. Among them, in consideration of the hue required for an optical element, heat resistance, etc., the hue of a color filter toned using the isoindolinone pigment is close to the three primary colors of NTSC. I. Pigment Yellow 11
0 is particularly preferred.
【００１０】これらのイソインドリノン系顔料を溶解さ
せるのに使用する硫酸の濃度は、イソインドリノン系顔
料が溶解し、かつスルホン化等の化学反応を受けない範
囲であれば特に限定されないが、通常７０〜１００重量
％の範囲であり、特に９５〜９８重量％の市販の濃硫酸
が使用できれば、経済的であり、操作的にも有利であ
る。The concentration of sulfuric acid used to dissolve these isoindolinone pigments is not particularly limited as long as the isoindolinone pigment is dissolved and is not subjected to a chemical reaction such as sulfonation. Usually, it is in the range of 70 to 100% by weight, and particularly if 95 to 98% by weight of commercially available concentrated sulfuric acid can be used, it is economical and operationally advantageous.
【００１１】硫酸の使用割合は、イソインドリノン系顔
料の硫酸への溶解性に依存するものの、イソインドリノ
ン系顔料が完全に溶解する範囲であれば特に限定されな
いが、品質の安定化や経済性を考慮すると、イソインド
リノン系顔料１重量部に対して硫酸３〜５０重量部の範
囲が好ましく、イソインドリノン系顔料１重量部に対し
て硫酸５〜２０重量部の範囲が特に好ましい。イソイン
ドリノン系顔料１重量部に対する硫酸の量が３重量部よ
りも少ない場合、イソインドリノン系顔料を完全に溶解
させるのに時間がかかり、生産性が低下するだけでな
く、製造操作中の吸湿によりイソインドリノン系顔料が
微視的レベルで析出し、製品の品質を低下させる傾向に
あるので好ましくない。イソインドリノン系顔料１重量
部に対する硫酸の量が５０重量部よりも多い場合、経済
的に不利であるばかりでなく、廃水が増大し、環境負荷
の面でも不利益を生ずる傾向にあるので好ましくない。The proportion of sulfuric acid used depends on the solubility of the isoindolinone pigment in sulfuric acid, but is not particularly limited as long as the isoindolinone pigment is completely dissolved, but the quality is stabilized and the economy is reduced. In consideration of properties, the range of 3 to 50 parts by weight of sulfuric acid is preferable for 1 part by weight of the isoindolinone pigment, and the range of 5 to 20 parts by weight of sulfuric acid is particularly preferable for 1 part by weight of the isoindolinone pigment. When the amount of sulfuric acid is less than 3 parts by weight based on 1 part by weight of the isoindolinone pigment, it takes time to completely dissolve the isoindolinone pigment, which not only lowers the productivity but also reduces the productivity during the manufacturing operation. Due to moisture absorption, the isoindolinone pigment is precipitated at a microscopic level, which tends to deteriorate the quality of the product, which is not preferable. When the amount of sulfuric acid is more than 50 parts by weight based on 1 part by weight of the isoindolinone pigment, it is not only economically disadvantageous, but also waste water increases, which is also disadvantageous in terms of environmental load. Absent.
【００１２】希釈水の割合は、イソインドリノン系顔料
硫酸溶液の液量１に対して希釈水の液量３〜５０の範囲
が好ましく、イソインドリノン系顔料硫酸溶液の液量１
に対して希釈水の液量７〜２５の範囲が特に好ましい。
希釈水の液量がイソインドリノン系顔料硫酸溶液の液量
１に対して３よりも少ない場合、希釈熱による温度上昇
が著しく、製造操作上危険であるだけでなく、熱により
顔料一次粒子が成長し、品質を低下させる傾向にあるの
で好ましくない。希釈水の液量がイソインドリノン系顔
料硫酸溶液の液量１に対して５０よりも多い場合、反応
設備の容量が過大となり、経済的に不利であり、さらに
廃水量の増大という問題も生ずる傾向にあるので好まし
くない。The proportion of the diluting water is preferably in the range of 3 to 50 with respect to the liquid volume of the isoindolinone pigment sulfuric acid solution, and the liquid volume of the isoindolinone pigment sulfuric acid solution is 1 to 3.
On the other hand, the range of the liquid amount of the dilution water is 7 to 25 is particularly preferable.
When the amount of the dilution water is less than 3 with respect to the amount 1 of the solution of the isoindolinone-based pigment sulfuric acid solution, the temperature rise due to the heat of dilution is not only dangerous in the manufacturing operation, but also the primary particles of the pigment may be heated. It is not preferable because it tends to grow and deteriorate in quality. When the amount of the diluting water is more than 50 with respect to the amount 1 of the solution of the isoindolinone-based pigment sulfuric acid solution, the capacity of the reaction equipment becomes too large, which is economically disadvantageous and causes a problem of increasing the amount of waste water. It is not preferable because it tends to occur.
【００１３】本発明の製造方法により得られたイソイン
ドリノン系顔料は、ウェットケーキとして、あるいは乾
燥粉砕した後、ドライ顔料として、印刷インキ、塗料、
プラスチック、金属インキ、捺染剤、文具、トナー、ジ
ェットインキ等、種々の物品の着色剤として用いること
ができるが、その鮮明性、透明性、耐熱性を活かしてカ
ラーフィルター等の光学素子に、特に好適に用いること
ができる。The isoindolinone-based pigment obtained by the production method of the present invention is used as a wet cake or after drying and pulverization, as a dry pigment, printing ink, paint,
It can be used as a colorant for various articles such as plastics, metal inks, textile printing agents, stationery, toners, jet inks, etc., but it is particularly useful for optical elements such as color filters because of its clearness, transparency and heat resistance. It can be preferably used.
【００１４】着色剤として用いる場合、得られた顔料を
そのまま使用することもでき、また、界面活性剤、樹
脂、ロジン、顔料誘導体等で処理した顔料を使用するこ
ともできる。When used as a colorant, the obtained pigment can be used as it is, or a pigment treated with a surfactant, a resin, a rosin, a pigment derivative or the like can be used.
【００１５】本発明のイソインドリノン系顔料を用いて
光学素子を作成するには、ガラス板や透明樹脂フィルム
等の透明な基板上に、少なくとも本発明によるイソイン
ドリノン系顔料を含有する薄膜を形成させればよい。薄
膜の形成方法の例としては、スピンコート法、印刷法、
電解法、電着法等、顔料分散体を用いる湿式プロセス
と、蒸着、スパッタリング等の乾式プロセスが挙げられ
るが、本発明の製造方法により製造されたイソインドリ
ノン系顔料の特徴を活かすには、湿式プロセスが好まし
い。In order to prepare an optical element using the isoindolinone pigment of the present invention, a thin film containing at least the isoindolinone pigment of the present invention is formed on a transparent substrate such as a glass plate or a transparent resin film. It may be formed. Examples of thin film forming methods include spin coating, printing,
Electrolytic method, electrodeposition method, wet process using a pigment dispersion, and vapor deposition, dry processes such as sputtering, but to take advantage of the characteristics of the isoindolinone pigment produced by the production method of the present invention, Wet processes are preferred.
【００１６】湿式プロセスによる薄膜形成方法に用い
る、本発明のイソインドリノン系顔料を含有する顔料分
散体には製膜性を有する樹脂を加えることもできるし、
界面活性剤、分散剤、消泡剤、レベリング剤等の添加剤
を加えることもできる。A resin having film-forming property can be added to the pigment dispersion containing the isoindolinone pigment of the present invention, which is used in the method for forming a thin film by a wet process.
Additives such as a surfactant, a dispersant, an antifoaming agent, and a leveling agent can also be added.
【００１７】製膜性を有する樹脂としては、例えば、ポ
リエステル樹脂、ポリカーボネート樹脂、ポリビニルブ
チラール樹脂、ポリビニルカルバゾール樹脂、ポリスチ
レン樹脂、ポリ酢酸ビニル樹脂、ポリ塩化ビニル樹脂、
ポリ塩化ビニリデン樹脂、ポリフッ化ビニリデン樹脂、
アクリル樹脂、メタクリル樹脂、シリコーン樹脂、アル
キッド樹脂、メラミン樹脂、メラミン−アルキッド樹
脂、フェノール樹脂、ポリアミド樹脂、ポリウレタン樹
脂、ポリイミド樹脂、エポキシ樹脂、フェノキシ樹脂、
スチレン−ブタジエン共重合体、スチレン−無水マレイ
ン酸共重合体、塩化ビニル−酢酸ビニル共重合体、塩化
ビニル−酢酸ビニル−無水マレイン酸共重合体等が挙げ
られる。また、熱、光、電子線等の作用によりこれらの
樹脂を生成し得る樹脂前駆体を用いることもできる。Examples of the film-forming resin include polyester resin, polycarbonate resin, polyvinyl butyral resin, polyvinyl carbazole resin, polystyrene resin, polyvinyl acetate resin, polyvinyl chloride resin,
Polyvinylidene chloride resin, polyvinylidene fluoride resin,
Acrylic resin, methacrylic resin, silicone resin, alkyd resin, melamine resin, melamine-alkyd resin, phenolic resin, polyamide resin, polyurethane resin, polyimide resin, epoxy resin, phenoxy resin,
Styrene-butadiene copolymer, styrene-maleic anhydride copolymer, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, and the like. In addition, a resin precursor that can generate these resins by the action of heat, light, an electron beam, or the like can also be used.
【００１８】顔料分散体の調製に使用する溶剤として
は、例えば、トルエン、キシレン、ミネラルスピリット
の如き炭化水素類；アセトン、メチルエチルケトン、メ
チルイソブチルケトン、シクロヘキサノンの如きケトン
類；ジクロロメタン、ジクロロエタン、トリクロロエタ
ン、トリクロロエチレン、クロロベンゼンの如きハロゲ
ン化炭化水素類；テトロヒドロフラン、ジオキサン、モ
ノグライム、ジグライム、アニソールの如きエーテル
類；メタノール、エタノール、プロパノール、ブタノー
ル、メチルセロソルブ、エチルセロソルブ、ブチルセロ
ソルブ、シクロヘキサノール、２−メトキシ−１−プロ
パノール、２−ブトキシ−１−プロパノールの如きアル
コール類；酢酸エチル、酢酸プロピル、酢酸ブチル、セ
ロソルブアセテート、ブチルセロソルブアセテート、酢
酸２−メトキシ−１−プロピル、酢酸２−ブトキシ−１
−プロピルの如きエステル類；ジメチルホルムアミド、
Ｎ−メチルピロリドンの如きアミド類；水等が挙げられ
る。これらの溶剤は、２種以上混合して用いることもで
きる。Examples of the solvent used for preparing the pigment dispersion include hydrocarbons such as toluene, xylene and mineral spirit; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; dichloromethane, dichloroethane, trichloroethane and trichloroethylene. , Halogenated hydrocarbons such as chlorobenzene; ethers such as tetrohydrofuran, dioxane, monoglyme, diglyme and anisole; methanol, ethanol, propanol, butanol, methyl cellosolve, ethyl cellosolve, butyl cellosolve, cyclohexanol, 2-methoxy-1. Alcohols such as propanol, 2-butoxy-1-propanol; ethyl acetate, propyl acetate, butyl acetate, cellosolve acetate, Chill cellosolve acetate, acetic acid 2-methoxy-1-propyl acetate, 2-butoxy -1
-Esters such as propyl; dimethylformamide,
Amides such as N-methylpyrrolidone; water and the like. These solvents may be used as a mixture of two or more kinds.
【００１９】顔料分散体を調製するには、本発明のイソ
インドリノン系顔料と溶剤、および必要に応じて製膜性
を有する樹脂、添加剤等を、ボールミル、ビーズミル、
サンドミル、パールミル、ペイントシェーカー、サンド
グラインダー、アトライター、ディスパーザー、ホモミ
キサー、超音波分散機等の分散手段により分散すればよ
い。To prepare a pigment dispersion, the isoindolinone pigment of the present invention, a solvent, and, if necessary, a resin having film-forming properties, additives, etc. are ball milled, bead milled,
It may be dispersed by a dispersing means such as a sand mill, a pearl mill, a paint shaker, a sand grinder, an attritor, a disperser, a homomixer and an ultrasonic disperser.
【００２０】[0020]
【実施例】以下、実施例比較例を用いて本発明を更に詳
細に説明する。なお、以下の実施例および比較例におい
て、「部」は『重量部』を意味する。EXAMPLES The present invention will be described in more detail below with reference to examples and comparative examples. In the following examples and comparative examples, “part” means “part by weight”.
【００２１】＜実施例１＞９８重量％硫酸８００部に、
粗製のＣ．Ｉ．ピグメント イエロー １１０１００部
を溶解させた。晶析槽に水９０００部を加え、晶析槽を
冷却、攪拌しながら、該硫酸溶液を４５０部／時間の流
量で添加し、希釈、析出させた。析出後のスラリー温度
は１０℃であった。<Example 1> 800 parts by weight of 98% by weight sulfuric acid,
Crude C.I. I. Pigment Yellow 110 (100 parts) was dissolved. 9000 parts of water was added to the crystallization tank, and the sulfuric acid solution was added at a flow rate of 450 parts / hour while cooling and stirring the crystallization tank for dilution and precipitation. The slurry temperature after precipitation was 10 ° C.
【００２２】得られた顔料を瀘過した後、残渣の洗液が
中性となるまで水洗し、Ｃ．Ｉ．ピグメント イエロー
１１０のウェットケーキを得た。得られたウェットケ
ーキを９０℃で乾燥させた後、粉砕して、ドライ顔料を
得た。After filtering the obtained pigment, it is washed with water until the washing liquid of the residue becomes neutral, and C.I. I. Pigment Yellow 110 wet cake was obtained. The obtained wet cake was dried at 90 ° C. and then pulverized to obtain a dry pigment.
【００２３】＜実施例２＞実施例１において、析出後の
顔料スラリーを顔料スラリー温度４０℃まで加熱した以
外は、実施例１と同様にして、Ｃ．Ｉ．ピグメント イ
エロー １１０顔料を得た。<Example 2> In the same manner as in Example 1 except that the pigment slurry after precipitation was heated to a pigment slurry temperature of 40 ° C in Example 1, C.I. I. Pigment Yellow 110 pigment was obtained.
【００２４】＜実施例３＞実施例１において、析出後の
顔料スラリーを顔料スラリー温度７０℃まで加熱した以
外は、実施例１と同様にして、Ｃ．Ｉ．ピグメント イ
エロー １１０顔料を得た。<Example 3> The same procedure as in Example 1 was repeated except that the pigment slurry after precipitation was heated to a pigment slurry temperature of 70 ° C. I. Pigment Yellow 110 pigment was obtained.
【００２５】＜実施例４＞実施例１において、得られた
ウェットケーキを水９０００部中に解膠し、顔料スラリ
ーを６０℃まで加熱した後、濾過し、残渣を水洗して、
Ｃ．Ｉ．ピグメント イエロー １１０のウェットケー
キを得た以外は、実施例１と同様にして、Ｃ．Ｉ．ピグ
メント イエロー １１０顔料を得た。Example 4 In Example 1, the obtained wet cake was peptized in 9000 parts of water, the pigment slurry was heated to 60 ° C., filtered, and the residue was washed with water.
C. I. Pigment Yellow 110 wet cake, except that a wet cake of C.I. I. Pigment Yellow 110 pigment was obtained.
【００２６】＜比較例１＞ジメチルホルムアミド（以
下、ＤＭＦと省略する。）８００部に、２８重量％のソ
ジウムメチラートのメタノール溶液２００部およびＣ．
Ｉ．ピグメント イエロー １１０ ２００部を加え溶
解させた。この溶液にｐＨ６となるまで酢酸を加えて、
顔料を析出させた。得られた顔料を、瀘過し、残渣を水
洗して、Ｃ．Ｉ．ピグメントイエロー １１０のウェッ
トケーキを得た。<Comparative Example 1> 800 parts of dimethylformamide (hereinafter abbreviated as DMF) was added to 200 parts of a methanol solution of 28 wt% sodium methylate and C.I.
I. Pigment Yellow 110 (200 parts) was added and dissolved. Add acetic acid to this solution until pH 6
The pigment was precipitated. The pigment obtained is filtered and the residue is washed with water to give C.I. I. Pigment Yellow 110 wet cake was obtained.
【００２７】このようにして得たウェットケーキをＤＭ
Ｆ３０００部中にリパルプし、８０℃まで加熱した。得
られた顔料を瀘過し、残渣を水洗し、Ｃ．Ｉ．ピグメン
ト１１０のウェットケーキを得た。得られたウェットケ
ーキを９０℃で乾燥させた後、粉砕して、ドライ顔料を
得た。The wet cake thus obtained was DM
It was repulped in 3000 parts of F and heated to 80 ° C. The obtained pigment is filtered, the residue is washed with water, and C.I. I. A wet cake of Pigment 110 was obtained. The obtained wet cake was dried at 90 ° C. and then pulverized to obtain a dry pigment.
【００２８】＜実施例５＞（光学素子の作成および評
価） ガラス製容器に、実施例１で得たＣ．Ｉ．ピグメント
イエロー １１０のドライ顔料２部、紫外線硬化型アク
リル樹脂（大日本インキ化学(株)製の「ユニディックＳ
５−１２２」）４部、２−ブトキシ−１−プロパノール
９４部および０．４ｍｍのジルコニアビーズ３００部を
入れ、ペイントシェーカーを用いて２時間振盪して、塗
布液を調製した。<Example 5> (Preparation and evaluation of optical element) The C.V. obtained in Example 1 was placed in a glass container. I. Pigment
2 parts of dry pigment of Yellow 110, UV curable acrylic resin (“Unidick S
5-122 ″) 4 parts, 2-butoxy-1-propanol 94 parts and 0.4 mm zirconia beads 300 parts were put and shaken for 2 hours using a paint shaker to prepare a coating solution.
【００２９】このようにして得た塗布液をスピンコータ
ー（ミカサ(株)製の「１Ｈ−３Ｄ型」）を用いて、ガラ
ス板（コーニング(株)製の「７０５９」）上に塗布し、
乾燥させた後、紫外線を照射することによって紫外線硬
化型アクリル樹脂を硬化させて光学素子として使用でき
る着色ガラス板を得た。なお、回転塗布条件は、２００
ｒｐｍで１０秒、次いで２０００ｒｐｍで３０秒とし
た。The coating solution thus obtained was applied onto a glass plate ("7059" manufactured by Corning Co., Ltd.) using a spin coater ("1H-3D type" manufactured by Mikasa Co., Ltd.),
After drying, the ultraviolet curable acrylic resin was cured by irradiating with ultraviolet rays to obtain a colored glass plate that can be used as an optical element. The spin coating condition is 200
The rpm was 10 seconds and then 2000 rpm for 30 seconds.
【００３０】このようにして得た光学素子の透過スペク
トルを分光光度計（(株)日立製作所製の「Ｕ−３５００
型」）にて測定した結果、波長５５０ｎｍでの透過率は
８２．５％、波長４５０ｎｍでの透過率は０．４％であ
った。The transmission spectrum of the optical element thus obtained was measured by a spectrophotometer (“U-3500” manufactured by Hitachi, Ltd.).
As a result, the transmittance at a wavelength of 550 nm was 82.5% and the transmittance at a wavelength of 450 nm was 0.4%.
【００３１】次に、この光学素子を、恒温加熱槽（(株)
いすず製作所製の「ＰＣＰ−３４ＥＤ」）で２５０℃で
１時間加熱し、耐熱試験を行った後、同様に、光学素子
の透過スペクトルを測定した結果、波長５５０ｎｍの透
過率は８１．９％、波長４５０ｎｍでの透過率は０．４
％であった。Next, this optical element was placed in a constant temperature heating tank (available from Co., Ltd.).
After heating for 1 hour at 250 ° C. with “PCP-34ED” manufactured by Isuzu Mfg. Co., Ltd., and conducting a heat resistance test, the transmission spectrum of the optical element was measured in the same manner. Transmittance at wavelength 450nm is 0.4
%Met.
【００３２】＜実施例６＞実施例５において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のドライ
顔料２部に代えて、実施例２で得たＣ．Ｉ．ピグメント
イエロー １１０のドライ顔料２部を用いた以外は、
実施例５と同様にして、光学素子を得た。<Embodiment 6> In Embodiment 5, Embodiment 1
C. obtained in I. Pigment Yellow 110 in place of 2 parts of the dry pigment, the C.I. I. Pigment Yellow 110 except that 2 parts of the dry pigment are used.
An optical element was obtained in the same manner as in Example 5.
【００３３】このようにして得た光学素子の波長５５０
ｎｍでの透過率は８３．２％、波長４５０ｎｍでの透過
率は０．５％であった。The wavelength 550 of the optical element thus obtained
The transmittance at 8 nm was 83.2%, and the transmittance at a wavelength of 450 nm was 0.5%.
【００３４】また、実施例５と同様にして、耐熱試験後
に光学素子の透過スペクトルを測定した結果、波長５５
０ｎｍでの透過率は８２．７％、波長４５０ｎｍでの透
過率は０．５％であった。In the same manner as in Example 5, the transmission spectrum of the optical element was measured after the heat resistance test.
The transmittance at 0 nm was 82.7% and the transmittance at a wavelength of 450 nm was 0.5%.
【００３５】＜実施例７＞実施例５において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のドライ
顔料２部に代えて、実施例３で得たＣ．Ｉ．ピグメント
イエロー １１０のドライ顔料２部を用いた以外は、
実施例４と同様にして光学素子を得た。<Embodiment 7> In Embodiment 5, Embodiment 1
C. obtained in I. Pigment Yellow 110, in place of 2 parts of the dry pigment, the C.I. I. Pigment Yellow 110 except that 2 parts of the dry pigment are used.
An optical element was obtained in the same manner as in Example 4.
【００３６】このようにして得た光学素子の波長５５０
ｎｍでの透過率は８２．０％、波長４５０ｎｍでの透過
率は０．４％であった。The wavelength 550 of the optical element thus obtained
The transmittance at 8 nm was 82.0%, and the transmittance at a wavelength of 450 nm was 0.4%.
【００３７】また、実施例５と同様にして、耐熱試験後
に光学素子の透過スペクトルを測定した結果、波長５５
０ｎｍでの透過率は８１．０％、波長４５０ｎｍでの透
過率は０．４％であった。In the same manner as in Example 5, the transmission spectrum of the optical element was measured after the heat resistance test.
The transmittance at 0 nm was 81.0% and the transmittance at a wavelength of 450 nm was 0.4%.
【００３８】＜実施例８＞実施例５において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のドライ
顔料２部に代えて、実施例４で得たＣ．Ｉ．ピグメント
イエロー １１０のドライ顔料２部を用いた以外は、
実施例４と同様にして光学素子を得た。<Embodiment 8> In Embodiment 5, Embodiment 1
C. obtained in I. Pigment Yellow 110 in place of 2 parts of the dry pigment, the C.I. I. Pigment Yellow 110 except that 2 parts of the dry pigment are used.
An optical element was obtained in the same manner as in Example 4.
【００３９】このようにして得た光学素子の波長５５０
ｎｍでの透過率は８２．８％、波長４５０ｎｍでの透過
率は０．５％であった。The wavelength 550 of the optical element thus obtained
The transmittance at 8 nm was 82.8%, and the transmittance at a wavelength of 450 nm was 0.5%.
【００４０】また、実施例５と同様にして、耐熱試験後
に光学素子の透過スペクトルを測定した結果、波長５５
０ｎｍでの透過率は８２．２％、波長４５０ｎｍでの透
過率は０．５％であった。In the same manner as in Example 5, the transmission spectrum of the optical element was measured after the heat resistance test.
The transmittance at 0 nm was 82.2% and the transmittance at a wavelength of 450 nm was 0.5%.
【００４１】＜比較例２＞実施例５において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のドライ
顔料２部に代えて、比較例１で得たＣ．Ｉ．ピグメント
イエロー １１０のドライ顔料２部を用いた以外は、
実施例４と同様にして光学素子を得た。Comparative Example 2 In Example 5, Example 1
C. obtained in I. Pigment Yellow 110 in place of 2 parts of the dry pigment, the C.I. I. Pigment Yellow 110 except that 2 parts of the dry pigment are used.
An optical element was obtained in the same manner as in Example 4.
【００４２】このようにして得た光学素子の波長５５０
ｎｍでの透過率は５０．３％、波長４５０ｎｍでの透過
率は１．２％であり、色純度、透明性が実施例５で得た
光学素子よりも劣っていた。The wavelength 550 of the optical element thus obtained
The transmittance at 5 nm was 50.3% and the transmittance at a wavelength of 450 nm was 1.2%, and the color purity and transparency were inferior to those of the optical element obtained in Example 5.
【００４３】また、実施例５と同様にして、耐熱試験後
に光学素子の透過スペクトルを測定した結果、波長５５
０ｎｍでの透過率は４８．２％、波長４５０ｎｍでの透
過率は１．０％であり、耐熱性試験後においても、実施
例５で得た光学素子よりも劣っていた。In the same manner as in Example 5, the transmission spectrum of the optical element was measured after the heat resistance test.
The transmittance at 0 nm was 48.2% and the transmittance at a wavelength of 450 nm was 1.0%, which was inferior to the optical element obtained in Example 5 even after the heat resistance test.
【００４４】＜比較例３＞実施例５において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のドライ
顔料２部に代えて、Ｃ．Ｉ．ピグメント イエロー ８
３（大日本インキ化学工業(株)製の「Ｓｙｍｕｌｅｒ
Ｆａｓｔ Ｙｅｌｌｏｗ ４１８１」）のドライ顔料２
部を用いた以外は、実施例４と同様にして光学素子を得
た。Comparative Example 3 In Example 5, Example 1
C. obtained in I. Pigment Yellow 110, instead of 2 parts of the dry pigment, C.I. I. Pigment Yellow 8
3 (“Symulator” manufactured by Dainippon Ink and Chemicals, Inc.)
Fast Yellow 4181 ") dry pigment 2
An optical element was obtained in the same manner as in Example 4 except that the parts were used.
【００４５】このようにして得た光学素子の波長５５０
ｎｍでの透過率は６５．６％、波長４５０ｎｍでの透過
率は１．２％であり、色純度、透明性が実施例５で得た
光学素子よりも劣っていた。The wavelength 550 of the optical element thus obtained
The transmittance at 6 nm was 65.6%, the transmittance at a wavelength of 450 nm was 1.2%, and the color purity and transparency were inferior to those of the optical element obtained in Example 5.
【００４６】また、実施例５と同様にして、耐熱試験後
に光学素子の透過スペクトルを測定した結果、波長５５
０ｎｍでの透過率は５２．３％、波長４５０ｎｍでの透
過率は０．９％であり、耐熱性試験後においても、実施
例４で得た光学素子よりも劣っていた。In the same manner as in Example 5, the transmission spectrum of the optical element was measured after the heat resistance test.
The transmittance at 0 nm was 52.3% and the transmittance at a wavelength of 450 nm was 0.9%, which was inferior to the optical element obtained in Example 4 even after the heat resistance test.
【００４７】＜実施例９＞実施例１で得たＣ．Ｉ．ピグ
メント イエロー １１０のウェット顔料とポリオキシ
エチレンドデシルエーテル（和光純薬(株)製）より調製
した水性分散液を用い、ケミストリーレターズ誌１９８
９年１１３７ページ記載の方法に従って、電解法により
ＩＴＯガラス電極上にＣ．Ｉ．ピグメント イエロー
１１０の薄膜を形成させて、光学素子を作成した。<Example 9> The C.I. I. Pigment Yellow 110 wet pigment and an aqueous dispersion prepared from polyoxyethylene dodecyl ether (manufactured by Wako Pure Chemical Industries, Ltd.) were used. Chemistry Letters magazine 198
9: 1137, C.I. I. Pigment yellow
An optical element was prepared by forming 110 thin films.
【００４８】このようにして得た光学素子の透過スペク
トルを、実施例５と同様にして測定した結果、波長５５
０ｎｍでの透過率は８３．１％、波長４５０ｎｍでの透
過率は０．５％であった。The transmission spectrum of the optical element thus obtained was measured in the same manner as in Example 5, and as a result, the wavelength 55
The transmittance at 0 nm was 83.1% and the transmittance at a wavelength of 450 nm was 0.5%.
【００４９】＜実施例１０＞実施例９において、実施例
１で得たＣ．Ｉ．ピグメント イエロー １１０のウェ
ット顔料に代えて、実施例２で得たＣ．Ｉ．ピグメント
イエロー １１０のウェット顔料を用いた以外は、実
施例９と同様にして光学素子を得た。<Example 10> In Example 9, the C.I. I. Pigment Yellow 110, instead of the wet pigment of C.I. I. Pigment Yellow 110, except that a wet pigment was used, an optical element was obtained in the same manner as in Example 9.
【００５０】このようにして得た光学素子の波長５５０
ｎｍでの透過率は８３．７％、波長４５０ｎｍでの透過
率は０．５％であった。The wavelength 550 of the optical element thus obtained
The transmittance at 8 nm was 83.7%, and the transmittance at a wavelength of 450 nm was 0.5%.
【００５１】＜実施例１１＞実施例９において、実施例
１で得たＣ．Ｉ．ピグメント イエロー １１０のウェ
ット顔料に代えて、実施例３で得たＣ．Ｉ．ピグメント
イエロー １１０のウェット顔料を用いた以外は、実
施例９と同様にして光学素子を得た。<Example 11> In Example 9, the C.I. I. Pigment Yellow 110 in place of the wet pigment, the C.I. I. Pigment Yellow 110, except that a wet pigment was used, an optical element was obtained in the same manner as in Example 9.
【００５２】このようにして得た光学素子の波長５５０
ｎｍでの透過率は８２．８％、波長４５０ｎｍでの透過
率は０．４％であった。The wavelength 550 of the optical element thus obtained
The transmittance at 8 nm was 82.8%, and the transmittance at a wavelength of 450 nm was 0.4%.
【００５３】＜実施例１２＞実施例９において、実施例
１で得たＣ．Ｉ．ピグメント イエロー １１０のウェ
ット顔料に代えて、実施例４で得たＣ．Ｉ．ピグメント
イエロー １１０のウェット顔料を用いた以外は、実
施例９と同様にして光学素子を得た。<Example 12> In Example 9, the C.I. I. Pigment Yellow 110, instead of the wet pigment of C.I. I. Pigment Yellow 110, except that a wet pigment was used, an optical element was obtained in the same manner as in Example 9.
【００５４】このようにして得た光学素子の波長５５０
ｎｍでの透過率は８３．２％、波長４５０ｎｍでの透過
率は０．６％であった。The wavelength 550 of the optical element thus obtained
The transmittance at 8 nm was 83.2%, and the transmittance at a wavelength of 450 nm was 0.6%.
【００５５】＜比較例４＞実施例９において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のウェッ
ト顔料に代えて、比較例１で得たＣ．Ｉ．ピグメント
イエロー １１０のウェット顔料を用いた以外は、実施
例１３と同様にして光学素子を得た。Comparative Example 4 In Example 9, Example 1
C. obtained in I. Pigment Yellow 110 in place of the wet pigment, the C.I. I. Pigment
An optical element was obtained in the same manner as in Example 13 except that the wet pigment of Yellow 110 was used.
【００５６】このようにして得た光学素子の波長５５０
ｎｍでの透過率は５３．２％、波長４５０ｎｍでの透過
率は１．２％であり、色純度、透明性が実施例９で得た
光学素子よりも劣っていた。The wavelength 550 of the optical element thus obtained
The transmittance at 5 nm was 53.2%, the transmittance at a wavelength of 450 nm was 1.2%, and the color purity and transparency were inferior to those of the optical element obtained in Example 9.
【００５７】＜比較例５＞実施例９において、実施例１
で得たＣ．Ｉ．ピグメント イエロー １１０のウェッ
ト顔料に代えて、Ｃ．Ｉ．ピグメント イエロー ８３
（大日本インキ化学工業(株)製の「Ｓｙｍｕｌｅｒ Ｆ
ａｓｔ Ｙｅｌｌｏｗ ４１８１」）のウェット顔料を
用いた以外は、実施例９と同様にして光学素子を得た。<Comparative Example 5> In Example 9, Example 1
C. obtained in I. Pigment Yellow 110, instead of the wet pigment, C.I. I. Pigment Yellow 83
(“Symulator F” manufactured by Dainippon Ink and Chemicals, Inc.
optical element was obtained in the same manner as in Example 9 except that the wet pigment of “ast Yellow 4181”) was used.
【００５８】このようにして得た光学素子の波長５５０
ｎｍでの透過率は６７．１％、波長４５０ｎｍでの透過
率は１．３％であり、色純度、透明性が実施例９で得た
光学素子よりも劣っていた。The wavelength 550 of the optical element thus obtained
The transmittance at 6 nm was 67.1%, the transmittance at a wavelength of 450 nm was 1.3%, and the color purity and transparency were inferior to those of the optical element obtained in Example 9.
【００５９】＜実施例１３＞（カラーフィルター適性の
評価） 実施例５で得た光学素子のコントラストを、バックライ
ト（明拓システム(株)製：輝度６０００カンデラ／
ｍ2 ）、一対の偏光板（ＮＰＦ−Ｇ１２２９ＤＵＮ：日
東電工(株)製／ＯＡ−２無アルカリガラス：日本電気硝
子(株)製）および色彩輝度計（ＢＭ−７型：(株)トプコ
ン製）よりなるコントラスト比測定装置を用いて測定し
た結果、９１０であった。<Example 13> (Evaluation of color filter suitability) The contrast of the optical element obtained in Example 5 was compared with that of a backlight (manufactured by Meitaku System Co., Ltd .: luminance 6000 candela /
m 2 ), a pair of polarizing plates (NPF-G1229DUN: manufactured by Nitto Denko Corporation / OA-2 alkali-free glass: manufactured by Nippon Electric Glass Co., Ltd.) and a color luminance meter (BM-7 type: manufactured by Topcon Corporation) It was 910 as a result of the measurement using the contrast ratio measuring device.
【００６０】＜比較例６＞実施例１３において、実施例
５で得た光学素子に代えて、比較例２で得た光学素子を
用いた以外は、実施例１３と同様にしてコントラスト比
を測定した結果、６９０であった。Comparative Example 6 The contrast ratio was measured in the same manner as in Example 13 except that the optical element obtained in Comparative Example 2 was used instead of the optical element obtained in Example 5. The result was 690.
【００６１】＜比較例７＞実施例１３において、実施例
５で得た光学素子に代えて、比較例３で得た光学素子を
用いた以外は、実施例１３と同様にしてコントラスト比
を測定した結果、８００であった。Comparative Example 7 The contrast ratio was measured in the same manner as in Example 13 except that the optical element obtained in Comparative Example 3 was used in place of the optical element obtained in Example 5. The result was 800.
【００６２】[0062]
【発明の効果】本発明の製造方法により製造されたイソ
インドリノン系顔料は、鮮明性、透明性、耐熱性に優れ
ており、光学素子、特にカラーフィルター用の顔料とし
て好適に使用することができる。The isoindolinone-based pigment produced by the production method of the present invention is excellent in sharpness, transparency and heat resistance and can be suitably used as a pigment for optical elements, especially color filters. it can.
Claims (8)
解し、次いで該硫酸溶液を水中に加えて析出させること
を特徴とするイソインドリノン系顔料の製造方法。1. A method for producing an isoindolinone pigment, which comprises dissolving a crude isoindolinone pigment in sulfuric acid, and then adding the sulfuric acid solution to water for precipitation.
メント イエロー１１０である請求項１記載の製造方
法。2. An isoindolinone pigment is C.I. I. Pigment Yellow 110, The manufacturing method according to claim 1.
請求項１または２記載の製造方法。3. The method according to claim 1, wherein the water temperature after precipitation is in the range of 0 to 80 ° C.
る請求項１または２記載の製造方法。4. The production method according to claim 1, wherein the water temperature after precipitation is in the range of 20 to 50 ° C.
再度水中に解膠し、一定時間加熱する請求項１、２、３
または４記載の製造方法。5. After precipitation in water, the precipitated pigment is filtered off,
4. Peptization again in water and heating for a certain period of time.
Or the production method according to 4.
求項５記載の製造方法。6. The manufacturing method according to claim 5, wherein the heating temperature is in the range of 40 to 80 ° C.
の方法で得られた黄色有機顔料を画素中に含有すること
を特徴とする光学素子。7. An optical element containing a yellow organic pigment obtained by the method according to claim 1, 2, 3, 4, 5 or 6 in a pixel.
るカラーフィルター。8. A color filter comprising the optical element according to claim 7 as a constituent element.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8094097A JPH09279052A (en) | 1996-04-16 | 1996-04-16 | Production of isoindolinone pigment and optical element using the pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8094097A JPH09279052A (en) | 1996-04-16 | 1996-04-16 | Production of isoindolinone pigment and optical element using the pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09279052A true JPH09279052A (en) | 1997-10-28 |
Family
ID=14100955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8094097A Pending JPH09279052A (en) | 1996-04-16 | 1996-04-16 | Production of isoindolinone pigment and optical element using the pigment |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH09279052A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001064534A (en) * | 1999-06-21 | 2001-03-13 | Toyo Ink Mfg Co Ltd | Green pigment composition containing no halogen |
| JP2009543917A (en) * | 2006-07-18 | 2009-12-10 | ビーエーエスエフ ソシエタス・ヨーロピア | Isoindoline pigment |
-
1996
- 1996-04-16 JP JP8094097A patent/JPH09279052A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001064534A (en) * | 1999-06-21 | 2001-03-13 | Toyo Ink Mfg Co Ltd | Green pigment composition containing no halogen |
| JP2009543917A (en) * | 2006-07-18 | 2009-12-10 | ビーエーエスエフ ソシエタス・ヨーロピア | Isoindoline pigment |
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