JPS61218551A - Squarylium compound - Google Patents
Squarylium compoundInfo
- Publication number
- JPS61218551A JPS61218551A JP60057562A JP5756285A JPS61218551A JP S61218551 A JPS61218551 A JP S61218551A JP 60057562 A JP60057562 A JP 60057562A JP 5756285 A JP5756285 A JP 5756285A JP S61218551 A JPS61218551 A JP S61218551A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- solvent
- materials
- isopropylazulene
- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
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- C09K19/00—Liquid crystal materials
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- C09K19/60—Pleochroic dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Photoreceptors In Electrophotography (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（ａ）発明の目的
本発明は、広範囲の溶媒に溶解し、かつ溶液中における
極大吸収波長が７００〜８００ ｎｍの領域内にある新
規なスクアリリウム化合物に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Object of the Invention The present invention relates to a novel squarylium compound that is soluble in a wide range of solvents and has a maximum absorption wavelength in the solution range of 700 to 800 nm.
（産業上の利用分野）
本発明の化曾物は、レーザー光ｔ−光源とする各種情報
材料、友とえば各種の電子写真感光材料、光デイスク用
記録材料又は赤外線カットフィルター等の分野での有用
性が期待される。(Industrial Application Fields) The invention can be used in the fields of various information materials using laser light sources, such as various electrophotographic photosensitive materials, recording materials for optical discs, and infrared cut filters. Expected to be useful.
（従来技術）
成る種のスクアリリウム化合物が光導電性を示し、たと
えは電子写真感光体の電荷発生剤として使用されること
は既に知られている（％開昭４９〜１０５５３６号公報
）。(Prior Art) It is already known that certain squarylium compounds exhibit photoconductivity and are used, for example, as a charge generating agent for electrophotographic photoreceptors (Patent Publication No. 105536/1983).
しかし、従来知られ友スクアリリウム化合物は。However, the conventionally known friend squarylium compound is.
一般に溶液中での吸収極大波長はせいぜい６５０ｎｍ付
近と短く、また九とえばＮ、Ｎ−ツメチルホルムアミド
、Ｎ−メチルピロリドン、ホルムアミド。Generally, the absorption maximum wavelength in a solution is as short as around 650 nm, and examples include N,N-methylformamide, N-methylpyrrolidone, and formamide.
Ｎ、Ｎ−ジメチルアセトアミド等の限られ几溶媒に対し
てのみ可溶性で、ま九耐光性が不充分で安定性に欠ける
等の点からして、利用分野に制限があり、特にレーデ−
元を光源とする各種情報材料として使用するには満足で
きるものでなかつ几。It is soluble only in limited solvents such as N,N-dimethylacetamide, and has insufficient light resistance and stability, which limits its field of use.
It is not satisfactory for use as various information materials using the original light source.
（発明が解決せんとする問題点）
本発明は、溶液中での可視吸収スペクトルの極大吸収波
長が７００〜８００ｎｍの領域内にメジ、かつ多くの溶
媒に可溶性であるスクアリリウム化合物を提供せんとす
るものである。(Problems to be Solved by the Invention) The present invention aims to provide a squarylium compound that has a maximum absorption wavelength of 700 to 800 nm in the visible absorption spectrum in solution and is soluble in many solvents. It is something.
（ｂ）発明の構成
本発明のスクアリリウム化合物は、一般式で表わされる
化合物である。(b) Structure of the Invention The squarylium compound of the present invention is a compound represented by the general formula.
本発明の前記一般式（１）で表わされるスクアリリウム
化合物は、一般式
〔式中、Ｂ１． Ｒ２及びＲ３は前記一般式（１）にお
けるそれらと同一のものを示す。〕
で表わされる化合物と、構造式
で表わされる３、４−ジヒドロキシ−３−シクロブテン
−１，２−ジオン、すなわちスクアリック酸と七、溶媒
中で反応させることによって容易に製造することができ
る。The squarylium compound represented by the general formula (1) of the present invention has the general formula [wherein B1. R2 and R3 are the same as those in the general formula (1). ] It can be easily produced by reacting the compound represented by the following with 3,4-dihydroxy-3-cyclobutene-1,2-dione represented by the structural formula, that is, squaric acid, in a solvent.
前記一般式（ＩＩ）で表わ嘔れる原料化合物としては、
たとえば１．２−トリメチレン−５−イソプロピルアズ
レン、１．２−）ジメチレン−６−イングロビルアズレ
ン、１．２−トリメチレン−５−メチルアズレン、１．
２−トリメチレン−６−メチルアズレン、１．２−）リ
メチレンアズレン、１．２−テトラメチレン−アズレン
、１．２−テトラメチレン−５−メチルアズレン、１．
２−テトラメチレン−６−メチルアズレン、１．２−テ
トラメチレン−５−イソプロピルアズレン、１．２テト
ラメチレン−６−イソプロピルアズレン、１．２−（フ
タメチレン−５−メチルアズレ／、１．２−ペンタメチ
レン−６−メチルアズレン、１．２−ペンタメチレン−
５−イソ！ロピルアズレン、１．２−ペンタメチレン−
６−イソプロピルアズレン、１，２−へキサメチレン−
５−イソプロビルアズレン、１．２−ヘキサメチレン−
６−イソプロピルアズレ／、１．２−デカメチレン−５
−イソプロピルアズレン、１゜２−デカメチレン−６−
イソプロピルアズレン、１、２．３．４−テトラヒドロ
−３−メチル−ベンズ（、）アズレン％ １．２．３．
４−テトラヒドロ−３−ｔ＠ｒｔ−ブチル−ベンズ［、
）アズレン、ｌ−メチル−２−エチル−５−イソプロピ
ルアズレン、１−メチル−２−エチル−６−メチルアズ
レン、１−エチル−２−ｎ−プロピル−５−イソプロピ
ルアズレン、１−エチル−２−ｎ’−７’ロビルー６−
イソ！ロビルアズレン、１−ｎ−プロピル−２−ｎ−ブ
チル−５−インプロビルアズレン、１−イングロビル−
２−イソプロピル−５−イソプロビルアフラン、１−ｎ
−ブチル−２−ｎ−ペンチル−５−イソプロビルアズレ
ン、１−ｎ−ペンチル−２−ｎ−へキシル−６−イソプ
ロピルアフラン、１−ｎ−オクチル−２−ｎ−へキシル
−６−イソプロピルアフラン、１−ｎ−デシル−２−ｎ
−ウンデシル−５−イソプロピルアフラン等が挙げられ
る。The raw material compound represented by the general formula (II) is as follows:
For example, 1.2-trimethylene-5-isopropyl azulene, 1.2-)dimethylene-6-inglobil azulene, 1.2-trimethylene-5-methyl azulene, 1.
2-trimethylene-6-methylazulene, 1.2-)rimethyleneazulene, 1.2-tetramethylene-azulene, 1.2-tetramethylene-5-methylazulene, 1.
2-tetramethylene-6-methylazulene, 1.2-tetramethylene-5-isopropylazulene, 1.2-tetramethylene-6-isopropylazulene, 1.2-(phtamethylene-5-methylazulene/, 1.2-pentazulene) Methylene-6-methylazulene, 1,2-pentamethylene-
5-Iso! Lopylazulene, 1,2-pentamethylene-
6-isopropylazulene, 1,2-hexamethylene-
5-isopropylazulene, 1,2-hexamethylene-
6-isopropyl azure/1,2-decamethylene-5
-isopropylazulene, 1゜2-decamethylene-6-
Isopropylazulene, 1,2.3.4-Tetrahydro-3-methyl-benz(,)Azulene% 1.2.3.
4-tetrahydro-3-t@rt-butyl-benz[,
) Azulene, l-methyl-2-ethyl-5-isopropylazulene, 1-methyl-2-ethyl-6-methylazulene, 1-ethyl-2-n-propyl-5-isopropylazulene, 1-ethyl-2- n'-7' lobi-6-
Iso! lovil azulene, 1-n-propyl-2-n-butyl-5-improvil azulene, 1-inglovir-
2-isopropyl-5-isoprobylafuran, 1-n
-Butyl-2-n-pentyl-5-isopropylazulene, 1-n-pentyl-2-n-hexyl-6-isopropylafuran, 1-n-octyl-2-n-hexyl-6-isopropyl Afran, 1-n-decyl-2-n
-undecyl-5-isopropylafuran and the like.
ま几、その製造反応において用いられる溶媒としては、
たとえば、メタノール、エタノール、１−クロノ臂ノー
ル、イソグロノ臂ノール、１−ブタノール、２−ブタノ
ール、アミルアルコール、１−ヘキサノール、シクロヘ
キサノール、１−ヘプタツール、１−ノナノール等のア
ルコール類、又ハこれらのアルコール類と、ベンゼン、
トルエン、キシレン、クロルベンゼン等の芳香族炭化水
素との混合溶媒等があげられる。As for the solvent used in the manufacturing reaction,
For example, alcohols such as methanol, ethanol, 1-chrononol, isoglononol, 1-butanol, 2-butanol, amyl alcohol, 1-hexanol, cyclohexanol, 1-heptatool, 1-nonanol; alcohols and benzene,
Examples include mixed solvents with aromatic hydrocarbons such as toluene, xylene, and chlorobenzene.
ま九、その製造反応における反応温度としては、通常、
７０〜１５０℃、好ましくは９０〜１２０℃の温度が用
いられる〇
本発明のスクアリリウム化合物は広範囲の程々の溶媒に
可溶性である。たとえばクロロホルム、ジクロルメタン
、ジクロルエタン等メ含ハロｒン炭化水素系溶媒、ジエ
チルエーテル、ジオキサン、テトラヒドロフラン、ジメ
トキシエタン等のエーテル系溶媒、酢酸エチル等のエス
テル系溶媒、ベンゼン、トルエン、キシレン、クロルベ
ンゼン等の芳香族炭化水素系溶媒、アセトアミド、Ｎ、
Ｎ −ジメチルアセトアミド、Ｎ−メチルピロリドン等
のアミド系溶媒、メタノール、エタノール、メチルセル
ンルプ等のアルコール系溶媒、ジメチルスルホキシド等
の溶媒によく溶解する。Nine, the reaction temperature in the production reaction is usually
Temperatures of 70-150°C, preferably 90-120°C are used. The squarylium compounds of the present invention are soluble in a wide range of moderate solvents. For example, halogen-containing hydrocarbon solvents such as chloroform, dichloromethane, and dichloroethane, ether solvents such as diethyl ether, dioxane, tetrahydrofuran, and dimethoxyethane, ester solvents such as ethyl acetate, and benzene, toluene, xylene, and chlorobenzene. aromatic hydrocarbon solvent, acetamide, N,
It dissolves well in amide solvents such as N-dimethylacetamide and N-methylpyrrolidone, alcoholic solvents such as methanol, ethanol, and methylcernlup, and solvents such as dimethyl sulfoxide.
ま几、本発明のスクアリリウム化合物は、溶液中におけ
る可視吸収スペクトルの極大吸収波長が７００〜８００
ｎｍの領域内にメジ、耐光性が良好でるる。The squarylium compound of the present invention has a maximum absorption wavelength of 700 to 800 in the visible absorption spectrum in solution.
Good light resistance is achieved within the nanometer range.
（実施例） 以下に、実施例ｔ−ｉげてさらに詳述する。(Example) Further details will be given below with reference to Examples.
実施例１
３．４−ジヒドロキシ−３−シクロブテン−１，２−ジ
オン０．１２．９にｎ−ブチルアルコール１５−を加え
、約１００℃に加熱して溶解させ友。この溶液に１．２
−トリメチレン−５−イソプロピルアズレン０．４３Ｉ
Ｉ、及びベンゼン１０−を加え、９５〜１０５℃に加熱
し、かつ反応によって生成する水を共沸的に留去しなが
ら、約１時間攪拌して反応させ几。Example 1 15-n-butyl alcohol was added to 0.12.9 g of 3.4-dihydroxy-3-cyclobutene-1,2-dione and dissolved by heating to about 100°C. 1.2 in this solution
-trimethylene-5-isopropylazulene 0.43I
Add I and 10-benzene, heat to 95-105°C, and stir for about 1 hour to react while azeotropically distilling off the water produced by the reaction.
生成物を冷却し九のち、ｎ−へキサンを添加して析出し
友結晶をカラムクロマトグラフィーによシ精製して、構
造式
で表わされる化合物を得た。After cooling the product, n-hexane was added to precipitate the product, and the resulting crystals were purified by column chromatography to obtain a compound represented by the structural formula.
この化合物は２６９．０〜２７０．０℃の融点を示し、
クロロホルム溶液中での可視吸収スペクトルの極大吸収
が７４２ｎｍであっ几。This compound exhibits a melting point of 269.0-270.0°C,
The maximum absorption in the visible absorption spectrum in a chloroform solution is 742 nm.
この化合物をシアノビフェニル系液晶に０．３０重量％
溶解し、ブラックライト（東京芝浦電機社製ＰＬ−２０
８ＢＬＢ ）にて紫外線照射による耐光性試験を行り友
ところ、１５時間後でも安定であった。Add 0.30% by weight of this compound to cyanobiphenyl liquid crystal.
Dissolve and use a black light (PL-20 manufactured by Tokyo Shibaura Electric Co., Ltd.)
A light resistance test by ultraviolet irradiation was conducted at 8BLB) and it was found to be stable even after 15 hours.
実施例２〜１３
実施例１で用い九１．２−）’Ｊメチレンー５−イソグ
ロビルアズレンの代シに、第１表に示す各製品化合物の
置換基と同一の置換基含有する前記一般式（…）の各化
合物上それぞれ使用し、そのほかは実施例１の方法に準
じて反応させ、第１表にそれぞれ示す各製品化合物を得
た。Examples 2 to 13 In place of 91.2-)'J methylene-5-isoglobyl azulene used in Example 1, the above-mentioned general compound containing the same substituent as the substituent of each product compound shown in Table 1 Each compound of the formula (...) was used, and the reaction was otherwise carried out according to the method of Example 1 to obtain each product compound shown in Table 1.
得られ几各化会物Ｉロロホルム溶液中での可視吸収スペ
クトルの極太吸収は第１表にそれぞれ示すとおシでめり
友。The visible absorption spectra of the obtained compounds I in loloform solution are shown in Table 1.
（Ｃ）発明の効果等
本発明のスクアリリウム化合物は多くの溶媒に可溶性で
あシ、かつ溶媒溶液中での可視吸収スペクトルの極大吸
収波長が７００〜８００ｎｍの領域内にある。し友がっ
て、この化合物はレーザー光を光源とする各種の情報材
料、友とえはレーデ−書き込み液晶表示やレーザーを光
源とし良電子写真プリンターの電子写真感光材、レーザ
ーによシ書き込みと読み出しが可能な光ディスク用記録
材料、又は赤外線カットフィルターなどの分野で有用性
が期待される。(C) Effects of the Invention The squarylium compound of the present invention is soluble in many solvents, and the maximum absorption wavelength of the visible absorption spectrum in a solvent solution is within the range of 700 to 800 nm. As a result, this compound can be used in various information materials that use laser light as a light source, such as laser-written liquid crystal displays, electrophotographic photosensitive materials for electrophotographic printers that use laser as a light source, and laser-based writing and photosensitive materials. It is expected to be useful in fields such as readable recording materials for optical discs and infrared cut filters.
Claims (1)
アルキル基を示し、Ｒ＾１とＲ＾２とは互いに連結して
環状アルキレン基を形成していてもよい。 Ｒ＾３は水素原子又は炭素数１〜１３のアルキル基を示
す。） で表わされるスクアリリウム化合物。 ２）一般式 ▲数式、化学式、表等があります▼ （式中、Ｒ＾１及びＲ＾２はそれぞれ炭素数１〜８のア
ルキル基を示し、Ｒ＾１とＲ＾２とは互いに連結して環
状アルキレン基を形成していてもよい。Ｒ＾３は水素又
は炭素数１〜５のアルキル基を示す。）で表わされる特
許請求の範囲第１項記載のスクアリリウム化合物。[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 and R^2 each represent an alkyl group having 1 to 13 carbon atoms, and R^1 and R^ 2 and 2 may be connected to each other to form a cyclic alkylene group. R^3 represents a hydrogen atom or an alkyl group having 1 to 13 carbon atoms.) A squarylium compound represented by: 2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 and R^2 each represent an alkyl group having 1 to 8 carbon atoms, and R^1 and R^2 are connected to each other. 2. The squarylium compound according to claim 1, wherein R^3 represents hydrogen or an alkyl group having 1 to 5 carbon atoms.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60057562A JPS61218551A (en) | 1985-03-23 | 1985-03-23 | Squarylium compound |
| DE8585309198T DE3583013D1 (en) | 1984-12-19 | 1985-12-17 | SQUARILIUM COMPOUNDS AND LIQUID CRYSTAL COMPOSITIONS CONTAINING THEM. |
| EP85309198A EP0187015B1 (en) | 1984-12-19 | 1985-12-17 | Squarilium compound and liquid crystal composition containing the same |
| US07/605,215 US5037575A (en) | 1984-12-19 | 1990-10-29 | Squarilium compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60057562A JPS61218551A (en) | 1985-03-23 | 1985-03-23 | Squarylium compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61218551A true JPS61218551A (en) | 1986-09-29 |
Family
ID=13059270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60057562A Pending JPS61218551A (en) | 1984-12-19 | 1985-03-23 | Squarylium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61218551A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0326593A (en) * | 1989-06-16 | 1991-02-05 | Eastman Kodak Co | Infrared ray absorbing squaleirylium dye for dye donating element which is used for laser induction dye heat transfer |
| US5085909A (en) * | 1988-04-28 | 1992-02-04 | Ricoh Company, Ltd. | Squarylium compounds and optical information recording medium using the same |
| US5275917A (en) * | 1991-07-09 | 1994-01-04 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US5470683A (en) * | 1993-07-28 | 1995-11-28 | Brother Kogyo Kabushiki Kaisha | Photosensitive microcapsule toner |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
-
1985
- 1985-03-23 JP JP60057562A patent/JPS61218551A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5085909A (en) * | 1988-04-28 | 1992-02-04 | Ricoh Company, Ltd. | Squarylium compounds and optical information recording medium using the same |
| JPH0326593A (en) * | 1989-06-16 | 1991-02-05 | Eastman Kodak Co | Infrared ray absorbing squaleirylium dye for dye donating element which is used for laser induction dye heat transfer |
| JPH0512156B2 (en) * | 1989-06-16 | 1993-02-17 | Eastman Kodak Co | |
| US5275917A (en) * | 1991-07-09 | 1994-01-04 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US6171759B1 (en) | 1992-05-14 | 2001-01-09 | Brother Kogyo Kabushiki Kaisha | Photocurable composition |
| US5470683A (en) * | 1993-07-28 | 1995-11-28 | Brother Kogyo Kabushiki Kaisha | Photosensitive microcapsule toner |
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