JPH0571584B2 - - Google Patents
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- Publication number
- JPH0571584B2 JPH0571584B2 JP61091260A JP9126086A JPH0571584B2 JP H0571584 B2 JPH0571584 B2 JP H0571584B2 JP 61091260 A JP61091260 A JP 61091260A JP 9126086 A JP9126086 A JP 9126086A JP H0571584 B2 JPH0571584 B2 JP H0571584B2
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- Prior art keywords
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/0601—Acyclic or carbocyclic compounds
- G03G5/0609—Acyclic or carbocyclic compounds containing oxygen
- G03G5/0611—Squaric acid
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
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- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photoreceptors In Electrophotography (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
〔産業上の利用分野〕
本発明は、電子写真感光材料、光デイスク用記
録材料、太陽電池、赤外線カツトフイルターの分
野で有用なスクエアリリウム化合物の合成原料と
なる新規なシクロブテンジオン誘導体に関する。
〔従来の技術〕
従来、下記反応式（）および（）に示すよ
うに３，４−ジクロロ−３−シクロブテン−１，
２−ジオン（スクエアリツク酸塩化物）はルイス
酸触媒の存在下で芳香族化合物と反応して、対応
する３−アリール−４−クロロ−３−シクロブテ
ン−１，２−ジオンを生成することが知られてい
る。
[Industrial Application Field] The present invention relates to a novel cyclobutenedione derivative that is a raw material for the synthesis of squarerylium compounds useful in the fields of electrophotographic light-sensitive materials, recording materials for optical disks, solar cells, and infrared cut filters. [Prior Art] Conventionally, as shown in the following reaction formulas () and (), 3,4-dichloro-3-cyclobutene-1,
2-dione (squaric acid chloride) can react with aromatic compounds in the presence of a Lewis acid catalyst to form the corresponding 3-aryl-4-chloro-3-cyclobutene-1,2-dione. Are known.
【化】 〔B.R.Greenら，Syntesis，1974，46〕[C] [BR Green et al., Syntesis, 1974 , 46]
【化】
〔L.A.Wendlingら，J.Org、Chem.，42（７）
1126（1977）〕
これらの反応では、選択性に問題があり、特に
（）の反応では目的化合物（収率34％）のほか
に次式[C] [LAWendling et al., J.Org, Chem., 42 (7)
1126 (1977)] These reactions have problems with selectivity, especially in the reaction (), in addition to the target compound (yield 34%), the following formula
本発明の目的は電子写真感光体等の光導電材料
として有用なスクエアリリウム化合物の中間体で
ある新規なシクロブテンジオン誘導体を提供する
ことにある。
〔問題点を解決するための手段〕
本発明は、一般式（）
An object of the present invention is to provide a novel cyclobutenedione derivative which is an intermediate of a squarerylium compound useful as a photoconductive material such as an electrophotographic photoreceptor. [Means for solving the problem] The present invention solves the problem by solving the general formula ()
【式】
〔式中、Ｘは水素原子、フツ素原子、メチル基
または水酸基であり、R1およびR2は互に独立し
たものであつて、メチル基、ｐ−クロロベンジル
基、ペンタフルオロベンジル基、フエニル基、ｐ
−トリル基またはオクタデシル基であり、Ｙは塩
素原子または水酸基である。〕
で示される新規なシクロブテンジオン誘導体を提
供したものである。
一般式（）で示される本発明のジオン誘導体
は、下記の方法によつて製造することができる。
すなわち、一般式（）[Formula ] [ wherein, group, phenyl group, p
-tolyl group or octadecyl group, and Y is a chlorine atom or a hydroxyl group. ] A novel cyclobutenedione derivative represented by the following is provided. The dione derivative of the present invention represented by the general formula () can be produced by the following method. That is, the general formula ()
【式】
で示される３，４−ジクロロ−３−シクロブテン
−１，２−ジオンと一般式（）[Formula] 3,4-dichloro-3-cyclobutene-1,2-dione and general formula ()
【式】
〔式中、Ｘ、R1およびR2は前記と同じ意味を
表わす。〕
で示されるアニリン誘導体とを溶媒中で、あるい
は溶媒を用いることなく、ルイス酸触媒の存在下
あるいは触媒を用いることなく反応させることに
より、一般式（）中、Ｙが塩素原子を表わす一
般式（ａ）[Formula] [In the formula, X, R 1 and R 2 represent the same meanings as above. ] By reacting with the aniline derivative represented by in a solvent or without using a solvent, in the presence of a Lewis acid catalyst or without using a catalyst, the general formula () in which Y represents a chlorine atom can be obtained. (a)
【化】
〔式中、Ｘ、R1およびR2は前記と同じ意味を
表わす。〕
で示される本発明化合物が得られ、更に一般式
（ａ）の化合物を酢酸等の存在下で加水分解す
ることにより一般式（）中、Ｙが水酸基を表わ
す一般式（ｂ）[In the formula, X, R 1 and R 2 have the same meanings as above. ] The compound of the present invention represented by is obtained, and the compound of general formula (a) is further hydrolyzed in the presence of acetic acid etc. to obtain general formula (b) in which Y represents a hydroxyl group.
【化】
〔式中、Ｘ、R1およびR2は前記と同じ意味を
表わす。〕
で示される本発明化合物が得られる。
本発明の新規なシクロブテンジオン誘導体の具
体例を表１（一般式（ａ）のクロロシクロブテ
ンジオン誘導体）および表２（一般式（ｂ）の
ヒドロキシシクロブテンジオン誘導体）に構造式
で示す。[In the formula, X, R 1 and R 2 have the same meanings as above. ] The compound of the present invention represented by these is obtained. Specific examples of the novel cyclobutenedione derivatives of the present invention are shown in structural formulas in Table 1 (chlorocyclobutenedione derivatives of general formula (a)) and Table 2 (hydroxycyclobutenedione derivatives of general formula (b)).
【表】【table】
【表】【table】
【表】【table】
以下、実施例を挙げて本発明のシクロブテンジ
オン誘導体を説明する。
実施例 １
スクエアリツク酸塩化物15.1ｇ（0.1mol）およ
び三フツ化ホウ素エチルエーテル錯体13ml
（0.1mol）を塩化メチレン60mlに溶解し、Ｎ，Ｎ
−ジメチルアニリン63ml（0.5mol）と混合、室
温で５時間攪拌して反応を行なつた。反応終了
後、混合物を希塩酸、ついで水で洗浄し、カラム
クロマトグラフイーを用いて分離生成を行ない化
合物(1)19.0ｇ（収率81％）を得た。
mp：194〜195℃（分解）；
IR（KBr）：1802，1772，1754cm-1；
UV（CH2Cl2）：409nm；
元素分析：C12H10ClNO2として
計算値（％） 実測値（％）
Ｃ 61.16 61.32
Ｈ 4.28 4.17
Ｎ 5.94 5.84
実施例 ２
スクエアリツク酸塩化物15.1ｇ（0.1mol）を塩
化メチレン60mlに溶解し、Ｎ，Ｎ−ジメチルアニ
リン63ml（0.5mol）と混合、室温で10時間攪拌
し反応を行なつた。反応終了後、混合物を希塩
酸、ついで水で洗浄し、カラムクロマトグラフイ
ーを用いて分離精製を行ない、化合物(1)17.7ｇ
（収率75％）を得た。
実施例 ３
スクエアリツク酸塩化物3.00ｇ（0.020mol）を
塩化メチレン30mlに溶かし、塩化アルミニウム
2.67ｇ（0.020mol）を懸濁させ、氷冷、攪拌下
Ｎ，Ｎ−ジメチルアニリン2.43ｇ（0.020mol）を
滴下した。さらに2.5時間氷冷下で攪拌した後混
合物を希塩酸、ついで水で洗浄、カラムクロマト
グラフイーを用いて分離生成を行ない、化合物(1)
1.17ｇ（収率21％）を得た。この際副生成物とし
て１，２−付加体が0.13ｇ（収率２％）得られ
た。
実施例 ４
スクエアリツク酸塩化物15.1ｇ（0.1mol）およ
び三フツ化ホウ素エチルエーテル錯体13ml
（0.1mol）を塩化メチレン60mlに溶解し、Ｎ，Ｎ
−ジメチル−ｍ−トルイジン72ml（0.5mol）と
混合、室温で１時間攪拌し反応を行ない、以下実
施例１と同様に処理して化合物(2)16.8ｇ（収率67
％）を得た。
mp：170.5〜171.5℃（分解）；
IR（KBr）：1790，1770cm-1；
UV（CH2Cl2）：421nm；
元素分析：C13H12ClNO2として
計算値（％） 実測値（％）
Ｃ 62.53 62.48
Ｈ 4.84 4.79
Ｎ 5.61 5.60
実施例 ５
スクエアリツク酸塩化物7.5ｇ（0.05mol）を塩
化メチレン30mlに溶解し、Ｎ，Ｎ−ジメチル−ｍ
−トルイジン22ml（0.15mol）と混合、室温で５
時間攪拌し反応を行ない、以下実施例１と同様に
処理し、化合物(2)7.9ｇ（収率63％）を得た。
実施例 ６
スクエアリツク酸塩化物7.5ｇ（0.05mol）およ
び三フツ化ホウ素エチルエーテル錯体6.5ml
（0.05mol）を塩化メチレン30mlに溶解し、Ｎ，
Ｎ−ジメチル−ｍ−フルオロアニリン35ｇ
（0.25mol）と混合、室温で16時間攪拌し反応を
行ない、以下実施例１と同様に処理し、化合物(3)
9.1ｇ（収率72％）を得た。
mp：224（分解）；
IR（KBr）：1816，1784，1760cm-1；
UV（CH2Cl2）：402nm；
元素分析：C12H9ClFNO2として
計算値（％） 実測値（％）
Ｃ 56.82 56.85
Ｈ 3.58 3.39
Ｎ 5.52 5.39
実施例 ７
スクエアリツク酸塩化物7.5ｇ（0.05mol）を、
塩化メチレン30mlに溶解し、Ｎ，Ｎ−ジメチル−
ｍ−アミノフエノール13.7ｇ（0.1mol）を塩化メ
チレン100mlに溶解した溶液を５〜10℃で徐々に
加え、30分間攪拌した。反応終了後、生じた沈澱
を別し、カラムクロマトグラフイーを用いて分
離生成を行ない、化合物(4)6.3ｇ（収率50％）を
得た。
mp：207〜209℃（分解）；
IR（KBr）：1816，1766，1730cm-1；
UV（CH2Cl2）：421nm；
元素分析：C12H10ClNO3として
計算値（％） 実測値（％）
Ｃ 57.27 57.41
Ｈ 4.00 4.06
Ｎ 5.57 5.39
実施例 ８
スクエアリツク酸塩化物7.5ｇ（0.05mol）、Ｎ
−メチル−Ｎ−（ｐ−クロロベンジル）アニリン
35ｇ（0.15mol）および三フツ化ホウ素エチルエ
ーテル錯体6.5ml（0.05mol）を塩化メチレン100
mlに溶解し、室温で24時間攪拌した。以下実施例
１と同様に処理し、化合物(5)102ｇ（収率59％）
を得た。
mp：175〜176℃（分解）；
IR（KBr）：1800，1758cm-1；
UV（CH2Cl2）：405nm；
元素分析：C18H13Cl2NO2として
計算値（％） 実測値（％）
Ｃ 62.45 62.67
Ｈ 3.78 3.66
Ｎ 4.05 4.02
実施例 ９
スクエアリツク酸塩化物7.5ｇ（0.05mol）と
Ｎ，Ｎ−ジベンジルアニリン27.3ｇ（0.1mol）を
塩化メチレン50mlに溶解し、10時間、加熱還流し
た。放冷後、混合物を希塩酸、ついで水で洗浄、
カラムクロマトグラフイーにより分離生成を行な
い、化合物(7)14.3ｇ（収率74％）を得た。
mp：171〜173℃；
IR（KBr）：1756cm-1；
UV（CH2Cl2）：406nm；
元素分析：C24H18ClNO2として
計算値（％） 実測値（％）
Ｃ 74.32 74.21
Ｈ 4.68 4.75
Ｎ 3.61 3.69
実施例 10〜13
実施例１と同様の方法で化合物(6)，(8)，(9)，(10)
を合成した。結果を表３に示す。
Hereinafter, the cyclobutenedione derivative of the present invention will be explained with reference to Examples. Example 1 15.1 g (0.1 mol) of squaric acid chloride and 13 ml of boron trifluoride ethyl ether complex
(0.1 mol) in 60 ml of methylene chloride, N,N
The mixture was mixed with 63 ml (0.5 mol) of -dimethylaniline and stirred at room temperature for 5 hours to carry out the reaction. After the reaction was completed, the mixture was washed with dilute hydrochloric acid and then with water, and separated using column chromatography to obtain 19.0 g (yield: 81%) of compound (1). mp: 194-195℃ (decomposition); IR (KBr): 1802, 1772, 1754 cm -1 ; UV (CH 2 Cl 2 ): 409 nm; Elemental analysis: as C 12 H 10 ClNO 2 Calculated value (%) Actual value (%) C 61.16 61.32 H 4.28 4.17 N 5.94 5.84 Example 2 15.1 g (0.1 mol) of squaric acid chloride was dissolved in 60 ml of methylene chloride, mixed with 63 ml (0.5 mol) of N,N-dimethylaniline, and stirred at room temperature. The reaction was carried out by stirring for 10 hours. After the reaction was completed, the mixture was washed with dilute hydrochloric acid and then with water, and separated and purified using column chromatography to obtain 17.7 g of compound (1).
(yield 75%). Example 3 Dissolve 3.00 g (0.020 mol) of squaric acid chloride in 30 ml of methylene chloride, and dissolve aluminum chloride.
2.67 g (0.020 mol) was suspended, and 2.43 g (0.020 mol) of N,N-dimethylaniline was added dropwise under ice cooling and stirring. After stirring for another 2.5 hours under ice-cooling, the mixture was washed with dilute hydrochloric acid and then with water, and separated using column chromatography, yielding compound (1).
1.17g (yield 21%) was obtained. At this time, 0.13 g (yield 2%) of 1,2-adduct was obtained as a by-product. Example 4 15.1 g (0.1 mol) of squaric acid chloride and 13 ml of boron trifluoride ethyl ether complex
(0.1 mol) in 60 ml of methylene chloride, N,N
-dimethyl-m-toluidine (72 ml (0.5 mol)) was mixed with 72 ml (0.5 mol) of dimethyl-m-toluidine, stirred at room temperature for 1 hour to react, and then treated in the same manner as in Example 1 to obtain 16.8 g (yield: 67.
%) was obtained. mp: 170.5-171.5℃ (decomposition); IR (KBr): 1790, 1770 cm -1 ; UV (CH 2 Cl 2 ): 421 nm; Elemental analysis: as C 13 H 12 ClNO 2 Calculated value (%) Actual value (%) ) C 62.53 62.48 H 4.84 4.79 N 5.61 5.60 Example 5 7.5 g (0.05 mol) of squaric acid chloride was dissolved in 30 ml of methylene chloride, and N,N-dimethyl-m
- mixed with 22 ml (0.15 mol) of toluidine, at room temperature
The mixture was stirred for a period of time to carry out the reaction, and then treated in the same manner as in Example 1 to obtain 7.9 g (yield: 63%) of compound (2). Example 6 7.5 g (0.05 mol) of squaric acid chloride and 6.5 ml of boron trifluoride ethyl ether complex
(0.05 mol) was dissolved in 30 ml of methylene chloride, N,
35g N-dimethyl-m-fluoroaniline
(0.25 mol), stirred at room temperature for 16 hours to react, and then treated in the same manner as in Example 1 to form compound (3).
9.1 g (yield 72%) was obtained. mp: 224 (decomposition); IR (KBr): 1816, 1784, 1760 cm -1 ; UV (CH 2 Cl 2 ): 402 nm; Elemental analysis: as C 12 H 9 ClFNO 2 Calculated value (%) Actual value (%) C 56.82 56.85 H 3.58 3.39 N 5.52 5.39 Example 7 7.5 g (0.05 mol) of squaric acid chloride,
Dissolved in 30 ml of methylene chloride, N,N-dimethyl-
A solution of 13.7 g (0.1 mol) of m-aminophenol dissolved in 100 ml of methylene chloride was gradually added at 5 to 10°C and stirred for 30 minutes. After the reaction was completed, the resulting precipitate was separated and separated using column chromatography to obtain 6.3 g (yield 50%) of compound (4). mp: 207-209℃ (decomposition); IR (KBr): 1816, 1766, 1730 cm -1 ; UV (CH 2 Cl 2 ): 421 nm; Elemental analysis: as C 12 H 10 ClNO 3 Calculated value (%) Actual value (%) C 57.27 57.41 H 4.00 4.06 N 5.57 5.39 Example 8 Square acid chloride 7.5g (0.05mol), N
-Methyl-N-(p-chlorobenzyl)aniline
35 g (0.15 mol) and 6.5 ml (0.05 mol) of boron trifluoride ethyl ether complex in methylene chloride 100
ml and stirred at room temperature for 24 hours. The following treatment was carried out in the same manner as in Example 1, and 102 g of compound (5) (yield 59%) was obtained.
I got it. mp: 175-176℃ (decomposition); IR (KBr): 1800, 1758 cm -1 ; UV (CH 2 Cl 2 ): 405 nm; Elemental analysis: as C 18 H 13 Cl 2 NO 2 Calculated value (%) Actual value (%) C 62.45 62.67 H 3.78 3.66 N 4.05 4.02 Example 9 7.5 g (0.05 mol) of squaric acid chloride and 27.3 g (0.1 mol) of N,N-dibenzylaniline were dissolved in 50 ml of methylene chloride and dissolved for 10 hours. , heated to reflux. After cooling, the mixture was washed with dilute hydrochloric acid and then with water.
The product was separated and produced by column chromatography, and 14.3 g (yield 74%) of compound (7) was obtained. mp: 171-173℃; IR (KBr): 1756 cm -1 ; UV (CH 2 Cl 2 ): 406 nm; Elemental analysis: as C 24 H 18 ClNO 2 Calculated value (%) Actual value (%) C 74.32 74.21 H 4.68 4.75 N 3.61 3.69 Examples 10-13 Compounds (6), (8), (9), (10) were prepared in the same manner as in Example 1.
was synthesized. The results are shown in Table 3.
【表】
実施例 14
実施例１で得た化合物(1)19.0ｇ（0.08mol）に、
酢酸75mlおよび水25mlを加え、１時間加熱還流、
放冷後、沈澱物を別、水で洗浄し、化合物(11)
17.2ｇ（収率98％）を得た。
mp：＞240℃（徐々に分解）；
IR（KBr）：1772，1756，1710cm-1；
UV（H2Ｏ）：389nm；
元素分析：C12H11CO3として
計算値（％） 実測値（％）
Ｃ 66.35 66.34
Ｈ 5.10 5.01
Ｎ 6.45 6.35
実施例 15〜23
実施例14と同様の方法で化合物(12)〜(20)を合成し
た。結果を表４に示す。[Table] Example 14 To 19.0 g (0.08 mol) of compound (1) obtained in Example 1,
Add 75 ml of acetic acid and 25 ml of water, heat under reflux for 1 hour,
After cooling, the precipitate was separated and washed with water, and compound (11)
17.2g (yield 98%) was obtained. mp: >240℃ (gradual decomposition); IR (KBr): 1772, 1756, 1710 cm -1 ; UV (H 2 O): 389 nm; Elemental analysis: as C 12 H 11 CO 3 Calculated value (%) Actual value (%) C 66.35 66.34 H 5.10 5.01 N 6.45 6.35 Examples 15-23 Compounds (12)-(20) were synthesized in the same manner as in Example 14. The results are shown in Table 4.
【表】【table】
本発明は新規なシクロブテンジオン誘導体を提
供したものである。本発明のシクロブテンジオン
誘導体から、電子写真感光体の光導電材料等とし
て有用なスクエアリリウム化合物を容易に合成す
ることができる。
The present invention provides novel cyclobutenedione derivatives. Squarelylium compounds useful as photoconductive materials for electrophotographic photoreceptors can be easily synthesized from the cyclobutenedione derivatives of the present invention.
Claims (1)
または水酸基であり、R1およびR2は互に独立し
たものであつて、メチル基、ｐ−クロルベンジル
基、ペンタフルオロベンジル基、フエニル基、Ｐ
−トリル基またはオクタデシル基であり、Ｙは塩
素原子または水酸基である。〕 で示される新規なシクロブテンジオン誘導体。 ２ 一般式（ａ） 【式】 〔式中、Ｘ、R1およびR2は前記と同じ意味を
表わす。〕 で示される特許請求の範囲第１項に記載のシクロ
ブテンジオン誘導体。 ３ 一般式（ｂ） 【化】 〔式中、Ｘ、R1およびR2は前記と同じ意味を
表わす。〕 で示される特許請求の範囲第１項に記載のシクロ
ブテンジオン誘導体。[Claims] 1 General formula () [Formula] [In the formula, X is a hydrogen atom, a fluorine atom, a methyl group, or a hydroxyl group, and R 1 and R 2 are group, p-chlorobenzyl group, pentafluorobenzyl group, phenyl group, P
-tolyl group or octadecyl group, and Y is a chlorine atom or a hydroxyl group. ] A novel cyclobutenedione derivative represented by 2 General Formula (a) [Formula] [In the formula, X, R 1 and R 2 represent the same meanings as above. ] The cyclobutenedione derivative according to claim 1, which is represented by: 3 General Formula (b) [In the formula, X, R 1 and R 2 have the same meanings as above. ] The cyclobutenedione derivative according to claim 1, which is represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61091260A JPS62249953A (en) | 1986-04-22 | 1986-04-22 | Novel cyclobutenedione derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61091260A JPS62249953A (en) | 1986-04-22 | 1986-04-22 | Novel cyclobutenedione derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62249953A JPS62249953A (en) | 1987-10-30 |
| JPH0571584B2 true JPH0571584B2 (en) | 1993-10-07 |
Family
ID=14021447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61091260A Granted JPS62249953A (en) | 1986-04-22 | 1986-04-22 | Novel cyclobutenedione derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62249953A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005122320A1 (en) * | 2004-06-09 | 2008-04-10 | 協和発酵ケミカル株式会社 | Photoelectric conversion material, photoelectric conversion element and photoelectrochemical cell |
| JP4488963B2 (en) * | 2005-06-23 | 2010-06-23 | 株式会社Adeka | Optical recording material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4624904A (en) * | 1985-06-28 | 1986-11-25 | Xerox Corporation | Photoconductive imaging members with unsymmetrical squaraine compounds containing an hydroxyl group |
-
1986
- 1986-04-22 JP JP61091260A patent/JPS62249953A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62249953A (en) | 1987-10-30 |
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