JPH0881635A - Cationic dye and method for dyeing base material using the same - Google Patents
Cationic dye and method for dyeing base material using the sameInfo
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- JPH0881635A JPH0881635A JP6242386A JP24238694A JPH0881635A JP H0881635 A JPH0881635 A JP H0881635A JP 6242386 A JP6242386 A JP 6242386A JP 24238694 A JP24238694 A JP 24238694A JP H0881635 A JPH0881635 A JP H0881635A
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、天然材料または合成材
料、例えば紙、パルプ或いはアクリル等の繊維を着色す
るのに有用なカチオン染料及び染色方法に関する。FIELD OF THE INVENTION This invention relates to cationic dyes and dyeing processes useful for coloring fibers of natural or synthetic materials such as paper, pulp or acrylic.
【０００２】[0002]
【従来の技術】繊維材料、皮革、紙、パルプ等基材の染
色及び捺染には数多くの染料（例えば特公昭６３−６０
７９３，特公平３−２１９１公報など）が使用されてい
る。しかしながら染色性（染色速度、染着性等）におい
て満足できるものは少ない。特に紙及びパルプ等で鮮明
な染色物を得るにあたって、従来の染料は染色速度およ
び染着率等において満足できるものは少ない。特に紙及
びパルプ等の鮮明な染色物を得るにあたって従来の染料
は染着速度及び染着率が小さいために染色効率上問題が
あり、加えて染色物の水堅ろう度においても満足する結
果が得られなかった。2. Description of the Related Art Many dyes (for example, Japanese Examined Patent Publication No. 63-60) are used for dyeing and printing base materials such as fiber materials, leather, paper and pulp.
793, Japanese Patent Publication No. 3-2191, etc.) is used. However, few are satisfactory in dyeability (dyeing speed, dyeability, etc.). In particular, when obtaining a clear dyed product with paper, pulp, etc., few conventional dyes are satisfactory in dyeing speed and dyeing rate. In particular, when obtaining clear dyed products such as paper and pulp, conventional dyes have a problem in dyeing efficiency because the dyeing speed and dyeing ratio are small, and in addition, satisfactory results can be obtained in water fastness of dyed products. I couldn't do it.
【０００３】[0003]
【発明が解決しようとする課題】染色時間の短縮及び環
境保全の点から染着速度及び染着率が高く染色廃水が無
色に近くなり、また得られた染色物の水堅ろう度が良好
である染料の開発が望まれてきた。From the viewpoint of shortening the dyeing time and environmental protection, the dyeing speed and dyeing rate are high, the dyeing wastewater becomes nearly colorless, and the waterfastness of the obtained dyeing product is good. The development of dyes has been desired.
【０００４】[0004]
【課題を解決するための手段】基材例えば、繊維材料、
皮革、紙、パルプ等の染色及び捺染を実施するに当た
り、染色速度が高く、高い染着率を示し優れた水堅ろう
度をもつ鮮明な染料を見いだすべく鋭意研究した結果、
本発明に至ったものである。すなわち本発明は、下記一
般式（１）[Means for Solving the Problems] Substrate, for example, fiber material,
In carrying out dyeing and printing of leather, paper, pulp, etc., as a result of diligent research to find a clear dye having a high dyeing rate, a high dyeing rate and an excellent water fastness,
The present invention has been achieved. That is, the present invention provides the following general formula (1)
【０００５】[0005]
【化３】 （式中、Ｒ1 、Ｒ2 はＣ1 〜6 のアルキル基を表し、Ｙ
- はアニオンを表す。）で表わされるカチオン染料およ
びそれを用いる基材の染色法を提供するものである。[Chemical 3] (Wherein, R 1, R 2 represents an alkyl group of C 1 ~ 6, Y
- represents an anion. ) And a method for dyeing a substrate using the same.
【０００６】本発明による染料の構造的特徴は一般式
（１）で示される様にカチオン化されたピペラジンに発
色団が２分子付いているために、パルプでの染着力がさ
らに強くなり、染着率、染着速度を飛躍的に改善するこ
とが出来た。The structural characteristic of the dye according to the present invention is that, as shown by the general formula (1), two molecules of the chromophore are attached to cationized piperazine. We were able to dramatically improve the dressing rate and dyeing speed.
【０００７】本発明の一般式（１）で表わされるカチオ
ン染料は、まず一般式（２）で表わされる中間体化合物The cationic dye represented by the general formula (1) of the present invention is a compound represented by the general formula (2).
【０００８】[0008]
【化４】 （式中、Ｒ1 、Ｒ2 はＣ1 〜6 のアルキル基を表わ
す。）を合成し、[Chemical 4] (Wherein, R 1, R 2 is. Represents an alkyl group of C 1 ~ 6) were synthesized,
【０００９】その中間体化合物にジメチル硫酸のような
アルキル化剤を反応させて、カチオン化する２工程より
なっている。It comprises two steps of reacting the intermediate compound with an alkylating agent such as dimethylsulfate to cationize.
【００１０】その中間体化合物の合成については、一般
式（３）で表わされるアルデヒド化合物For the synthesis of the intermediate compound, an aldehyde compound represented by the general formula (3)
【００１１】[0011]
【化５】 （式中、Ｒ1 、Ｒ2 はＣ1 〜6 のアルキル基を表わ
す。）と次式で表わされる化合物、[Chemical 5] (Wherein, R 1, R 2 represents an alkyl group of C 1 ~ 6.) And is expressed by the following compounds,
【００１２】[0012]
【化６】 を有機溶媒中で塩基性触媒の存在下で縮合させる方法、
或いは一般式（４）で表わされる酸クロライド化合物[Chemical 6] A method of condensing in the presence of a basic catalyst in an organic solvent,
Alternatively, an acid chloride compound represented by the general formula (4)
【００１３】[0013]
【化７】 （式中、Ｒ1 、Ｒ2 はＣ1 〜6 のアルキル基を表わ
す。）と次式で表わされる化合物、[Chemical 7] (Wherein, R 1, R 2 represents an alkyl group of C 1 ~ 6.) And is expressed by the following compounds,
【化８】 を有機溶媒中で脱酸剤の存在下に縮合させて得る事が出
来る。Embedded image Can be obtained by condensation in an organic solvent in the presence of a deoxidizing agent.
【００１４】反応に使用される有機溶媒の例としては、
トルエン、クロルベンゼンの様なベンゼン系溶媒、テト
ラハイドロフラン、ジオキサンの様なエーテル系溶媒、
ヘキサン、シクロヘキサンの様なアルキル系溶媒、ジク
ロロエタン、クロロホルムの様なハロゲン化アルキル系
溶媒、ジメチルホルムアミド、ジメチルスルホオキサイ
ドの様な極性溶媒を挙げる事ができる。Examples of organic solvents used in the reaction include:
Benzene-based solvents such as toluene and chlorobenzene, ether-based solvents such as tetrahydrofuran and dioxane,
Examples thereof include alkyl solvents such as hexane and cyclohexane, halogenated alkyl solvents such as dichloroethane and chloroform, and polar solvents such as dimethylformamide and dimethyl sulfoxide.
【００１５】反応に使用される塩基性触媒の例として
は、ピリジン、ピペラジン、キノリン、モルホリン等が
挙げられる。Examples of the basic catalyst used in the reaction include pyridine, piperazine, quinoline, morpholine and the like.
【００１６】又、反応に使用される脱酸剤はトリエチル
アミン、ピリジン、Ｎ，Ｎ−ジメチルアニリン等の一般
的３級アミンを挙げることができる。The deoxidizing agent used in the reaction may be a general tertiary amine such as triethylamine, pyridine and N, N-dimethylaniline.
【００１７】メチル化剤としてはジメチル硫酸、ヨウ化
メチル等を挙げることができる。Examples of the methylating agent include dimethyl sulfate and methyl iodide.
【００１８】縮合反応終了後この新規カチオン染料は、
場合によっては反応触媒から分離される。また必要によ
っては一般式（１）のカチオン染料のアニオンは公知の
方法（たとえば特公昭３９−４８７９号公報）により水
溶解性良好な他のアニオンに置換することもできる。After completion of the condensation reaction, the new cationic dye is
In some cases, it is separated from the reaction catalyst. If necessary, the anion of the cationic dye of the general formula (1) can be replaced with another anion having good water solubility by a known method (for example, Japanese Patent Publication No. 39-4879).
【００１９】次に本発明の一般式（１）のカチオン染料
による基材の染色法について述べる。この新規カチオン
染料は、繊維材料、皮革、パルプおよび紙の染色に用い
る染料として、またそれら基材の捺染に用いるカラーイ
ンキの調製のため色素材として使用でき、更にガラスあ
るいは透明な合成樹脂フィルム上に設けられたゼラチ
ン、カゼイン等の天然蛋白質あるいは含窒素光硬化性樹
脂の薄膜を着色するためにも用いることができ、それら
はカラーフィルターとしても有用である。ゼラチン、カ
ゼイン等の天然蛋白質あるいは含窒素光硬化性樹脂から
なる薄膜は常法により例えばギ酸、酢酸、塩酸等で酸性
に調製された水性浴から３０〜１００℃の温度で着色さ
れる。Next, a method of dyeing a substrate with the cationic dye of the general formula (1) of the present invention will be described. This novel cationic dye can be used as a dye for dyeing textile materials, leather, pulp and paper, and as a color material for the preparation of color inks for printing those substrates, and on glass or transparent synthetic resin film. It can also be used for coloring a thin film of a natural protein such as gelatin or casein or a nitrogen-containing photocurable resin provided in the above, and they are also useful as a color filter. A thin film made of a natural protein such as gelatin or casein or a nitrogen-containing photocurable resin is colored at a temperature of 30 to 100 ° C. by an ordinary method from an aqueous bath acidified with formic acid, acetic acid, hydrochloric acid or the like.
【００２０】繊維材料としてはカチオン染料で染色でき
る材料、例えばアクリルニトリルのホモ重合体および混
合重合体、酸改質されたポリエステルおよびポリアミド
などの天然含窒素繊維、セルローズを含む材料例えば木
綿、再生セルローズ繊維、ポリビニルアルコール繊維等
があげられる。As the fiber material, a material which can be dyed with a cationic dye, for example, homopolymers and mixed polymers of acrylonitrile, natural nitrogen-containing fibers such as acid-modified polyester and polyamide, materials containing cellulose such as cotton, recycled cellulose Examples thereof include fibers and polyvinyl alcohol fibers.
【００２１】本発明の新規カチオン染料によるこれら繊
維材料の染色は常法により好ましくは中性ないし酸性水
媒質中からの常圧又は加圧による吸収染法あるいは水性
インキによるスプレー塗工、パデイングおよびプリント
などの連続染色によって実施される。この場合の繊維材
料の形態は単繊維およびその膠着物、糸、布、編物およ
び完成品である。これら染色物および捺染物はすぐれた
染色堅ろう性を有し、特にきわめて高い染着率とすぐれ
た水堅ろう度を示す。The dyeing of these fiber materials with the novel cationic dyes of the present invention is carried out by a conventional method, preferably by an absorption dyeing method in a neutral or acidic aqueous medium under normal pressure or pressure, or by spray coating, padding and printing with an aqueous ink. It is carried out by continuous staining such as. The form of the fiber material in this case is a single fiber and its agglomerates, yarns, cloths, knits and finished products. These dyes and prints have excellent fastness to dyeing, and particularly exhibit extremely high dyeing rate and excellent fastness to water.
【００２２】さらに本新規カチオン染料の好ましい用途
は各種のパルプおよび紙、とくに漂白または未漂白でサ
イジングされていないまたはサイジングされた紙類の染
色である。この新規カチオン染料はサイジング処理を施
していないパルプおよび紙（ナプキン、テーブルクロ
ス、衛生紙など）に対しても非常に大きい染着速度なら
びに非常に高い染着率を示す。この高い染着はその染色
廃水を無色に近いものとし、廃水規制および環境保全上
からもきわめて大きな利点といえる。A further preferred use of the novel cationic dyes is in the dyeing of various pulps and papers, especially bleached or unbleached, unsized or sized papers. This new cationic dye exhibits a very high dyeing speed and a very high dyeing rate even on unsized pulp and paper (napkins, table cloths, sanitary papers, etc.). This high dyeing makes the dyeing wastewater close to colorless, which is a great advantage from the viewpoint of wastewater regulation and environmental protection.
【００２３】染色はｐＨ値４〜８、ことに５〜７、染色
温度１０〜５０℃、好ましくは１５〜３０℃で行われ
る。そして得られた染色物は高いカラーバリューでかつ
鮮明であり、すぐれた染色堅ろう性を示す。とくに耐水
堅ろう度については、たとえば染色された紙と湿潤した
白紙を常温下で加圧接触させても染色紙から白紙に転染
（にじみ出し）はほとんどみられず、ミョーバン、アル
カリ、酸、アルコールに対してもすぐれた堅ろう性を示
すことから、ナプキン、テーブルクロスおよび衛生紙な
ど色のにじみ出しのとくに心配される紙の用途分野にき
わめて好適である。本新規カチオン染料による染料は紙
に対しきわめて高い親和性を有しかつ染着速度も大きい
ことから、紙の連続染色およびジェットプリンター用イ
ンキにも適用でき、なをかつ、皮革の染色（スプレー、
ハケ塗り、浸漬など）にも使用できる。The dyeing is carried out at a pH value of 4 to 8, preferably 5 to 7, and a dyeing temperature of 10 to 50 ° C., preferably 15 to 30 ° C. The resulting dyed product has a high color value and is clear and exhibits excellent dyeing fastness. In particular, with respect to water fastness, even if the dyed paper and the wet white paper are brought into contact with each other under pressure at room temperature, almost no transfer (bleeding) from the dyed paper to the white paper is observed, and alum, alkali, acid, alcohol Since it also has excellent fastness to paper, it is very suitable for application fields of paper such as napkins, table cloths and sanitary papers where color bleeding is particularly concerned. Since the dye with this novel cationic dye has an extremely high affinity for paper and has a high dyeing speed, it can be applied to continuous dyeing of paper and ink for jet printers, and to dye leather (spray,
It can also be used for brushing, dipping, etc.).
【００２４】[0024]
【実施例】次に実施例により本発明を更に詳細に説明す
るが、これに限定されるものではない。EXAMPLES The present invention will now be described in more detail by way of examples, which should not be construed as limiting the invention.
【００２５】実施例１ 中間体の合成Example 1 Synthesis of Intermediate
【化９】 ビス（２−シアノメチルカルボニルオキシエチル）ピペ
ラジン３．０８ｇ（０．０１モル）と４−ジエチルアミ
ノベンツアルデヒド３．５４ｇ（０．０２モル）をトル
エン６０ｍｌに分散させ、触媒としてピリジン０．２ｍ
ｌを加え、リフラックスを行った。この時に水分離器を
セットし、水の留出量で反応をチェックした。２時間反
応を行い、冷却後、析出した結晶をろ過、乾燥して黄色
結晶５．０１ｇを得た。赤外分析の結果、−ＣＮ ２２
１４ｃｍ-1，＞Ｃ＝Ｏ １７０１ｃｍ-1であり、融点
は、２０６〜２０８°であった。[Chemical 9] 3.08 g (0.01 mol) of bis (2-cyanomethylcarbonyloxyethyl) piperazine and 3.54 g (0.02 mol) of 4-diethylaminobenzaldehyde were dispersed in 60 ml of toluene, and 0.2 m of pyridine was used as a catalyst.
l was added and reflux was performed. At this time, the water separator was set and the reaction was checked by the amount of water distilled. After reacting for 2 hours and cooling, the precipitated crystals were filtered and dried to obtain 5.01 g of yellow crystals. As a result of infrared analysis, -CN 22
14cm -1, a> C = O 1701cm -1, a melting point was 206 - 208 °.
【００２６】なお、ビス（２−シアノメチルカルボニル
オキシエチル）ピペラジンの合成は下記の方法により行
った。ビス（２−ヒドロキシエチル）ピペラジン８．７
１ｇ（０．０５モル）とシアノ酢酸メチルエステル１
２．３９ｇ（０．１２５モル）をシクロヘキサン１５０
ｍｌに分散し、リフラックスを４時間行った。この時、
反応によって生成したメタノールは分離器を使用して分
離した。反応終了後、生成物はろ過、乾燥して、１４．
８０ｇの目的物を得た。赤外分析の結果、−ＣＮ ２２
１８ｃｍ-1，＞Ｃ＝Ｏ １７１５ｃｍ-1 The bis (2-cyanomethylcarbonyloxyethyl) piperazine was synthesized by the following method. Bis (2-hydroxyethyl) piperazine 8.7
1 g (0.05 mol) and cyanoacetic acid methyl ester 1
2.39 g (0.125 mol) of cyclohexane 150
It was dispersed in ml and refluxed for 4 hours. This time,
The methanol produced by the reaction was separated using a separator. After completion of the reaction, the product is filtered and dried, and 14.
80 g of the desired product was obtained. As a result of infrared analysis, -CN 22
18 cm -1 ,> C = O 1715 cm -1
【００２７】実施例２ 中間体の合成Example 2 Synthesis of Intermediate
【化１０】 ビス（２−ヒドロキシエチル）ピペラジン１．７４ｇ
（０．０１モル）とトリエチルアミン２．２３ｇ（０．
０２２モル）をジクロルメタン４０ｍｌに溶解し、１０
℃以下に冷却しながら、ジクロルメタン２０ｍｌに溶解
した４−ジエチルアミノ−α−シアノシンナモイルクロ
ライド５．２６ｇ（０．０２モル）を滴下した。滴下
後、リフラックスを２時間行った。冷却後、ジクロルメ
タンを回収し、残渣に水２００ｍｌを加え、ろ過、乾燥
して５．８１ｇの目的物を得た。融点２０６〜２０８℃
であった。[Chemical 10] 1.74 g of bis (2-hydroxyethyl) piperazine
(0.01 mol) and 2.23 g of triethylamine (0.
022 mol) in 40 ml of dichloromethane and dissolved in 10
5.26 g (0.02 mol) of 4-diethylamino-α-cyanocinnamoyl chloride dissolved in 20 ml of dichloromethane was added dropwise while cooling to below ℃. After dropping, reflux was performed for 2 hours. After cooling, dichloromethane was recovered, 200 ml of water was added to the residue, filtered and dried to obtain 5.81 g of the desired product. Melting point 206-208 ° C
Met.
【００２８】実施例３ 目的物の合成Example 3 Synthesis of desired product
【化１１】 式（１０）の化合物６．２７ｇ（０．０１モル）をクロ
ロホルム６０ｍｌに５０℃まで加温して溶解させ、同温
度でジメチル硫酸１．５１ｇ（０．０１２モル）を滴下
した。滴下後、６０℃で２時間反応を行った。冷却後、
１０％食塩水１００ｍｌを加え、クロロホルム層を分
液、脱水後、クロロホルムを回収、乾燥して、上記構造
式で示される最大吸収波長（λｍａｘ）４３３．０ｎｍ
の黄色染料６．７５ｇを得た。[Chemical 11] 6.27 g (0.01 mol) of the compound of the formula (10) was dissolved in 60 ml of chloroform by heating to 50 ° C., and 1.51 g (0.012 mol) of dimethylsulfate was added dropwise at the same temperature. After the dropping, the reaction was carried out at 60 ° C. for 2 hours. After cooling
100 ml of 10% saline was added, the chloroform layer was separated and dehydrated, chloroform was recovered and dried, and the maximum absorption wavelength (λmax) 433.0 nm represented by the above structural formula was obtained.
To obtain 6.75 g of yellow dye.
【００２９】実施例４ 未漂白亜硫酸パルプ５０％および機械パルプ５０％から
なる乾燥材料をビーター（Ｂｅａｔｅｒ）中で水を用い
て４０ＳＲフリーネス（Ｆｒｅｅｎｅｓｓ）にこう解
し、パルプ含有量３％になるよう水で調製する。この調
製液１００部に実施例３で得られたカチオン染料０．０
３部および酢酸０．０２部を加える。この混合物を約５
分間攪拌しロジンサイズ０．０３部および結晶硫酸アル
ミニウム０．０６部を加え、ひき続き５分間攪拌し、更
にこの液に水４００部を加えて希釈し、これをシーター
（ｓｈｅｅｔｅｒ）上で常法により抄紙した。この場
合、抄紙廃水の染料による着色はほとんどみとめられず
得られた着色紙はきわめて鮮明な黄色を示し、良好な耐
光及びすぐれた耐水堅ろう度を示した。Example 4 Dry material consisting of 50% unbleached sulphite pulp and 50% mechanical pulp was digested to 40SR Freeness with water in a Beater to give a pulp content of 3%. Prepare with water. The cationic dye obtained in Example 3 was added to 100 parts of this preparation liquid.
Add 3 parts and 0.02 part acetic acid. Approximately 5 of this mixture
After stirring for 3 minutes, 0.03 part of rosin size and 0.06 part of crystalline aluminum sulfate were added, followed by stirring for 5 minutes, and then 400 parts of water was added to this solution to dilute it, and this was diluted on a sheeter in a conventional manner Paper was made by. In this case, coloring of the papermaking wastewater with dyes was scarcely observed, and the obtained colored paper exhibited a very vivid yellow color, and showed good light resistance and excellent water fastness.
【００３０】比較例１ 実施例３で使用した染料の代りに次の構造式Comparative Example 1 The following structural formula was used instead of the dye used in Example 3.
【化１２】 で示される染料を使用する以外は実施例４と同様の方法
で抄紙染色したが、抄紙廃水にかなりの着色が見られ、
着色紙もかなり薄い着色であった。[Chemical 12] Papermaking dyeing was carried out in the same manner as in Example 4 except that the dye shown in was used. However, considerable coloring was observed in the papermaking wastewater,
The colored paper was also lightly colored.
【００３１】実施例５ 植物タンニンでなめした豚革１００部を、水２５０部お
よび実施例３で得られたカチオン染料０．２部からなる
５０℃の浴に入れて３０分間攪拌し、次いで同じ浴で、
スルホン化鯨油を主成分とするアニオン油脂液１０部で
６０分間処理する。次に常法により乾燥し、黄色の染色
革を得た。この染色革は洗濯堅ろう度は非常に良好であ
った。Example 5 100 parts of pig tanned leather tanned with vegetable tannins are placed in a bath of 250 parts of water and 0.2 parts of the cationic dye obtained in Example 3 at 50 ° C. and stirred for 30 minutes, then the same. In the bath
It is treated with 10 parts of anionic fat and oil liquid containing sulfonated whale oil as a main component for 60 minutes. Then, it was dried by a conventional method to obtain yellow dyed leather. The dyed leather had very good wash fastness.
【００３２】以下実施例６〜９で得られた染料を表１に
示す。染料の構造、紙を染色した時の色相、およびλｍ
ａｘを示した。The dyes obtained in Examples 6 to 9 are shown in Table 1 below. Structure of dye, hue when dyed paper, and λm
indicated ax.
【００３３】[0033]
【表１】 [Table 1]
【００３４】[0034]
【発明の効果】本発明によって得られたカチオン染料
は、基材に対する染着速度および染着率がきわめて高
く、かつ得られた染色又は着色基材の水堅ろう度が良好
であった。The cationic dye obtained according to the present invention has a very high dyeing speed and dyeing rate to a substrate, and the dyed or colored substrate obtained has good water fastness.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 鈴木 信夫 東京都北区神谷三丁目７番６号 保土谷化 学工業株式会社東京工場内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Nobuo Suzuki 3-7-6 Kamiya, Kita-ku, Tokyo Hodogaya Chemical Co., Ltd. Tokyo factory
Claims (2)
- はアニオンを表す。）で表わされるカチオン染料。1. The following general formula (1): (Wherein, R 1, R 2 represents an alkyl group of C 1 ~ 6, Y
- represents an anion. ) A cationic dye represented by.
- はアニオンを表す。）で表わされるカチオン染料を用
いることを特徴とする基材の染色方法。2. The following general formula (1): (Wherein, R 1, R 2 represents an alkyl group of C 1 ~ 6, Y
- represents an anion. ) A method for dyeing a substrate, which comprises using a cationic dye represented by
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| JP3598137B2 JP3598137B2 (en) | 2004-12-08 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012039286A1 (en) * | 2010-09-22 | 2012-03-29 | 株式会社Adeka | Pigment and colored photosensitive composition |
| WO2012101946A1 (en) * | 2011-01-25 | 2012-08-02 | 株式会社Adeka | Novel compound, dye and colored photosensitive composition |
-
1994
- 1994-09-12 JP JP24238694A patent/JP3598137B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012039286A1 (en) * | 2010-09-22 | 2012-03-29 | 株式会社Adeka | Pigment and colored photosensitive composition |
| US20130041062A1 (en) * | 2010-09-22 | 2013-02-14 | Adeka Corporation | Dye and coloring photosensitive composition |
| US8664289B2 (en) | 2010-09-22 | 2014-03-04 | Adeka Corporation | Dye and coloring photosensitive composition |
| JP5844267B2 (en) * | 2010-09-22 | 2016-01-13 | 株式会社Adeka | Dye and colored photosensitive composition |
| WO2012101946A1 (en) * | 2011-01-25 | 2012-08-02 | 株式会社Adeka | Novel compound, dye and colored photosensitive composition |
| US9029434B2 (en) | 2011-01-25 | 2015-05-12 | Adeka Corporation | Colored photosensitive composition |
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