JPH01146852A - Novel cyclobutenedione derivative - Google Patents
Novel cyclobutenedione derivativeInfo
- Publication number
- JPH01146852A JPH01146852A JP30586687A JP30586687A JPH01146852A JP H01146852 A JPH01146852 A JP H01146852A JP 30586687 A JP30586687 A JP 30586687A JP 30586687 A JP30586687 A JP 30586687A JP H01146852 A JPH01146852 A JP H01146852A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- cyclobutenedione
- represented
- same meaning
- derivative
- 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.)
- Granted
Links
- RGBVWCQARBEPPW-UHFFFAOYSA-N cyclobut-3-ene-1,2-dione Chemical class O=C1C=CC1=O RGBVWCQARBEPPW-UHFFFAOYSA-N 0.000 title claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 239000000463 material Substances 0.000 abstract description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002994 raw material Substances 0.000 abstract description 6
- 230000003287 optical effect Effects 0.000 abstract description 4
- SXOQOOQUBDERIZ-UHFFFAOYSA-N 3,4-dichlorocyclobut-3-ene-1,2-dione Chemical compound ClC1=C(Cl)C(=O)C1=O SXOQOOQUBDERIZ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- -1 chloroform) Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNJNUCYAVRRVMW-UHFFFAOYSA-N 3-chlorocyclobut-3-ene-1,2-dione Chemical class ClC1=CC(=O)C1=O DNJNUCYAVRRVMW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SCKHIBMTSKZHQF-UHFFFAOYSA-N 1,2-dichlorocyclobutene Chemical compound ClC1=C(Cl)CC1 SCKHIBMTSKZHQF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- JHXKRIRFYBPWGE-UHFFFAOYSA-K bismuth chloride Chemical compound Cl[Bi](Cl)Cl JHXKRIRFYBPWGE-UHFFFAOYSA-K 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- MHGIJXSAUHOIDU-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]acetamide Chemical compound CN(C)C1=CC=CC(NC(C)=O)=C1 MHGIJXSAUHOIDU-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
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、赤外線カットフィルターの分野で有用なスク
ェ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。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to electrophotographic photosensitive materials, recording materials for optical disks,
This invention relates to a new cyclobutenedione derivative that is a raw material for the synthesis of square lylium compounds useful in the fields of solar cells and infrared cut filters.
従来の技術
近年、ある種のスクアリリウム化合物が優れた光導電性
を示し、電子写真感光材料その他の用途に使用できるこ
とが報告されている（例えば、特開昭６０−１３６４５
２号公報、同６０−１４２９４６号公報、同６０−１４
２９４７号公報、同６１−１０５４０号公報、同６２−
４５０号公報参照）。BACKGROUND OF THE INVENTION In recent years, it has been reported that certain squarylium compounds exhibit excellent photoconductivity and can be used for electrophotographic light-sensitive materials and other applications (for example, Japanese Patent Laid-Open No. 60-13645
Publication No. 2, Publication No. 60-142946, Publication No. 60-14
No. 2947, No. 61-10540, No. 62-
(See Publication No. 450).
これらのスクアリリウム化合物は、原料物質として、ジ
クロロブテンジオンを用いて合成される。These squarylium compounds are synthesized using dichlorobutenedione as a raw material.
従来３，４−ジクロロ−３−シクロブテン１゜２−ジオ
ン（スクエアリック酸塩化物）は、下記反応式（１）及
び■で示されるように、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．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、次式で示される１、２−付加体く収率３％
）が副成する。Conventionally, 3,4-dichloro-3-cyclobutene 1°2-dione (squaric acid chloride) reacts with aromatic compounds in the presence of a Lewis acid catalyst, as shown in the following reaction formula (1) and (2). and the corresponding 3-aryl-4-chloro-3-cyclobutene 1. These reactions have problems with selectivity, especially in the reaction ①, the target compound (yield 34%).
), the 1,2-adduct represented by the following formula has a yield of 3%.
) is a by-product.
発明が解決しようとする問題点
芳香族化合物として、Ｎ、Ｎ−ジメチルアニリン等の第
三級芳香族アミンを用いてスクエアリンク酸塩化物との
フリーデルクラフッ反応を試みた例は、これまで報告さ
れていない。Problems to be Solved by the Invention Until now, there have been no examples in which a Friedel-Crach reaction with a square link acid chloride was attempted using a tertiary aromatic amine such as N,N-dimethylaniline as an aromatic compound. Not reported.
本発明者等は、−群の第三級芳香族アミンを用い、シク
ロブテンジオン誘導体を合成することについて検討した
結果、特定の第三級芳香族アミンを用いると、電子写真
感光材料その他の用途に使用できる新規なスクアリリウ
ム化合物を製造するための中間体となる新規なシクロブ
テンジオン誘導体が得られることを見出だした。The present inventors have studied the synthesis of cyclobutenedione derivatives using tertiary aromatic amines of group -3, and have found that using specific tertiary aromatic amines can be used in electrophotographic materials and other applications. It has been discovered that a new cyclobutenedione derivative can be obtained which is an intermediate for producing a new squarylium compound that can be used for.
したがって、本発明の目的は、電子写真感光材料その他
の用途に使用できる新規なスクアリリウム化合物を製造
するための中間体とな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。Therefore, an object of the present invention is to provide a novel cyclobutenedione derivative that is an intermediate for producing a novel squarylium compound that can be used in electrophotographic light-sensitive materials and other applications.
問題点を解決するための手段
本発明の新規なシクロブテンジオン誘導体は、入
（式中、Ｒ１、Ｒ２及びＲ３は、それぞれメチル基、エ
チル基、プロピル基又はブチル基を表わし、Ｘは塩素原
子又は水酸基を表わす）
で示される。Means for Solving the Problems The novel cyclobutenedione derivatives of the present invention are characterized in that: or hydroxyl group).
上記のシクロブテンジオン誘導体には、下記構造式（Ｉ
ａ）及び（Ｉｂ）が含まれる。The above cyclobutenedione derivative has the following structural formula (I
a) and (Ib) are included.
し−
（式中、Ｒ１、Ｒ２及びＲ３は、それぞれ前記と同じ意
味を表わす）
これ等の更に具体的な化合物としては、下記構造式のシ
クロブテンジオン誘導体を例示すること（式中、Ｒ１及
びＲ２は、それぞれ前記と同じ意味を表わす）
上記一般式（Ｉ）で示されるシクロブテンジオン誘導体
は、次のようにして製造することができる。(In the formula, R1, R2 and R3 each have the same meaning as above.) More specific examples of these compounds include cyclobutenedione derivatives of the following structural formula (wherein, R1 and R3 each have the same meanings as above). (R2 each represents the same meaning as defined above) The cyclobutenedione derivative represented by the above general formula (I) can be produced as follows.
下記構造式（ＩＩ）
で示される３、４−ジクロロ−３−シクロブテン−１，
２−ジオンと、下記一般式（Ｉ［［）（式中、Ｒ１、Ｒ
２及びＲ３は、それぞれ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反応させてクロロシクロ
ブテンジオン誘導体を合成し、所望により、加水分解す
ることによって得ることができる。3,4-dichloro-3-cyclobutene-1, represented by the following structural formula (II)
2-dione and the following general formula (I[[) (wherein, R1, R
2 and R3 each have the same meaning as above) A chlorocyclobutenedione derivative is synthesized by reacting it with an aniline derivative represented by the formula (2 and R3 each have the same meaning as above), and if desired, it can be obtained by hydrolysis.
上記の反応は、公知の類似の反応に準じて実施すること
ができる。The above reaction can be carried out according to known similar reactions.
即ち、まず、３，４−ジクロロ−３−シクロブテン−１
，２−ジオンと一般式（ＩＩ＞で示されるアニリン誘導
体とを反応させる。この反応は、それ等を、適当な溶剤
、例えば塩化メチレン、四塩化炭素〈クロロホルム等の
ハロゲン化炭化水素、ニトロベンゼン、エチルエーテル
、アセトニトリル等の通常のフリーデルクラフッ反応溶
媒に溶解し、所望ならば触媒、例えば三フッ化硼素エチ
ルエーテル錯体、塩化アルミニウム、塩化アンチモン、
塩化鉄（ＩＩ＞又は（■）、塩化チタン（ＩＶ）、塩化
錫（ＩＶＹ、塩化ビスマス（ＩＶ＞、塩化亜鉛（■）、
塩化水銀等の存在下、０〜４０℃において攪拌すること
によって行うことができる。That is, first, 3,4-dichloro-3-cyclobutene-1
, 2-dione and the aniline derivative represented by the general formula (II>).This reaction is performed by reacting them with a suitable solvent such as methylene chloride, carbon tetrachloride (halogenated hydrocarbon such as chloroform), nitrobenzene, Dissolved in common Friedel-Crach reaction solvents such as ethyl ether, acetonitrile, etc., and if desired a catalyst, such as boron trifluoride ethyl ether complex, aluminum chloride, antimony chloride,
Iron chloride (II> or (■), titanium chloride (IV), tin chloride (IVY), bismuth chloride (IV>), zinc chloride (■),
This can be carried out by stirring at 0 to 40°C in the presence of mercury chloride or the like.
合成されたクロロシクロブテンジオン誘導体は、所望に
より加水分解されるが、加水分解は、適当な酸、例えば
酢酸を含む水中で、加熱することによって実施される。The synthesized chlorocyclobutenedione derivative is hydrolyzed if desired, and the hydrolysis is carried out by heating in water containing a suitable acid, such as acetic acid.
本発明のシクロブテンジオン誘導体は、電子写真感光材
料、光デイスク用記録材料、太陽電池、赤外線カットフ
ィルターの分野で有用なスクェアリリウム化合物の合成
原料として有用である。例えば、本発明のシクロブテン
ジオン誘導体を、下記一般式（ＩＶ）で示されるアニリ
ン誘導体と縮合させることにより、種々のスクアリリウ
ム化合物を製造することができる。The cyclobutenedione derivative of the present invention is useful as a raw material for the synthesis of square aryllium compounds useful in the fields of electrophotographic light-sensitive materials, recording materials for optical disks, solar cells, and infrared cut filters. For example, various squarylium compounds can be produced by condensing the cyclobutenedione derivative of the present invention with an aniline derivative represented by the following general formula (IV).
（式中、Ｘは水素原子、メチル基、フッ素原子又は水酸
基を表わす）
実施例
以下、本発明の実施例を示す。(In the formula, X represents a hydrogen atom, a methyl group, a fluorine atom, or a hydroxyl group.) Examples Examples of the present invention are shown below.
実施例１
３．４−ジクロロ−３−シクロブテン−１，２−ジオン
１．９３ｇ（１２，８ミリモル〉及び３−アセチルア
ミノ−Ｎ、Ｎ−ジメチルアニリン ４．５２ｇ（２５，
４ミリモル）を塩化メチレン ２０ｍに溶解し、室温で
２時間攪拌し、反応を行なった。反応終了後、反応混合
物を希塩酸、次いで水で洗浄し、カラムクロマトグラフ
ィーを用いて分離精製を行ない、下記構造式で示される
クロロシクロブテンジオン化合物２．１６ｇ（収率５８
％）を得た。融点二ｍｐ＝２１８℃
この化合物の赤外吸収スペクトルは第１図に示す通りで
あり、紫外吸収スペクトル（最大）は、ＵＶ （ＣＨ２
Ｃｌ ２ ） ： ４３４ｎｍであった。又、元素分
析値は、Ｃ１４Ｈ１３ＣＩＮ２０３として、次の通りで
あった。Example 1 3.4-dichloro-3-cyclobutene-1,2-dione 1.93 g (12,8 mmol) and 3-acetylamino-N,N-dimethylaniline 4.52 g (25,
4 mmol) was dissolved in 20 m of methylene chloride and stirred at room temperature for 2 hours to carry out a reaction. After the reaction, the reaction mixture was washed with dilute hydrochloric acid and then with water, and separated and purified using column chromatography to obtain 2.16 g of a chlorocyclobutenedione compound (yield: 58
%) was obtained. Melting point 2mp = 218°C The infrared absorption spectrum of this compound is as shown in Figure 1, and the ultraviolet absorption spectrum (maximum) is UV (CH2
Cl 2 ): 434 nm. Moreover, the elemental analysis value was as follows as C14H13CIN203.
計算値（％） 実測値（％）
Ｃ５７，４５５７，２７
Ｈ４，４８４，３６
Ｎ ９，５７ ９．７５
実施例２
実施例１において得られたクロロシクロブテンジオン化
合物１．００９（３，４２ミリモル）に酢酸１０ｍ及び
水１威を加え、１０分間加熱還流させた後、放冷し、析
出する沈澱物を濾別し、下記構造式で示されるヒドロキ
シシクロブテンジオン化合物０．８６ｇ（収率９２％）
を得た。融点： ｍｐ＝２８０℃（分解）この化合物の
赤外吸収スペクトルは第２図に示す通りであり、紫外吸
収スペクトル（最大）は、ＵＶ （ＣＩ−１２ＣＩ ２
＞ ： ４１５ｎｍであった。又、元素分析値は、
Ｃ１４Ｈ１４Ｎ２ Ｃ４として、次の通りであった。Calculated value (%) Actual value (%) C57,4557,27 H4,484,36 N 9,57 9.75 Example 2 Chlorocyclobutenedione compound obtained in Example 1 1.009 (3,42 mmol) ) was added with 10 m of acetic acid and 1 part of water, heated under reflux for 10 minutes, allowed to cool, and the deposited precipitate was filtered to obtain 0.86 g of a hydroxycyclobutenedione compound represented by the following structural formula (yield: 92 %)
I got it. Melting point: mp=280°C (decomposition) The infrared absorption spectrum of this compound is as shown in Figure 2, and the ultraviolet absorption spectrum (maximum) is UV (CI-12CI 2
>: 415 nm. In addition, the elemental analysis value is
C14H14N2 C4 was as follows.
計算値（％） 実測値（％）
Ｃ、６１，３１６１，２９
）−１５，１５５，１Ｏ
Ｎ １０．２１ １０．０９実施例３〜８
目的化合物に対応する原料物質を選択し、実施例１にお
けると同様にして３，４−ジクロロ−３−シクロブテン
−１，２−ジオンと反応させ、第１表に示す化合物を製
造した。これ等の化合物の紫外吸収スペクトル（最大）
も又第１表に示す。Calculated value (%) Actual value (%) C, 61,3161,29)-15,155,1O N 10.21 10.09 Examples 3 to 8 A raw material corresponding to the target compound was selected, and Example 1 The compounds shown in Table 1 were prepared by reacting with 3,4-dichloro-3-cyclobutene-1,2-dione in the same manner as in . Ultraviolet absorption spectra (maximum) of these compounds
Also shown in Table 1.
実施例９〜１４
実施例３〜５によって得られた化合物を、実施例２にお
けると同様に処理して第２表に示す化合物を製造した。Examples 9-14 The compounds obtained in Examples 3-5 were treated in the same manner as in Example 2 to produce the compounds shown in Table 2.
これ等の化合物の紫外吸収スペクトル（最大）も又第２
表に示す。The ultraviolet absorption spectra (maximum) of these compounds are also second to none.
Shown in the table.
発明の効果
本発明のジクロブテンジオン誘導体は、新規な化合物で
あって、電子写真感光材料、光デイスク用記録材料、太
陽電池、赤外線カットフィルターの分野で有用なスクェ
アリリウム化合物の合成原料として使用することができ
る。本発明のジクロブテンジオン誘導体を用い、例えば
Ｎ、Ｎ−ジアルキルアニリン誘導体と反応させることに
よって合成されたスクアリリウム化合物を含有する電子
写真感光体は、可視領域から近赤外領域までの広い範囲
にわたって感度を有するものとなる。Effects of the Invention The dichlorobutenedione derivative of the present invention is a new compound and is used as a raw material for synthesis of square aryllium compounds useful in the fields of electrophotographic photosensitive materials, recording materials for optical disks, solar cells, and infrared cut filters. be able to. An electrophotographic photoreceptor containing a squarylium compound synthesized by using the dichlorobutenedione derivative of the present invention and reacting it with, for example, an N,N-dialkylaniline derivative has sensitivity over a wide range from the visible region to the near-infrared region. It will have the following.
第１図は実施例１のシクロブテンジオン化合物の赤外吸
収スペクトル図であり、第２図は実施例２のシクロブテ
ンジオン化合物の赤外吸収スペクトル図である。
手続補正書く自発）
昭和６３年 １月夕日
特許庁長官 小 川 邦 夫 膜
性 所 東京都港区赤坂３丁目３番５号名 称 （
５４９）富士ゼロックス株式会社代表者 小林陽太部
６、補正の内容
（′Ｉ）明細書の「２、特許請求の範囲」を別紙の通り
補正する。
２、特許請求の範囲
（１）下記一般式（Ｉ＞
＾
（式中、Ｒ１、Ｒ２及びＲ３は、それぞれメチル基、エ
チル基、プロピル基又はブチル基を表わし、Ｘは塩素原
子又は水酸基を表わす）
で示されるシクロブテンジオン誘導体。
■下記構造式（Ｉａ＞
（式中、Ｒ１、Ｒ２及びＲ３は、それぞれ前記と同じ意
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下記構造式（Ｉｂ＞
（式中、Ｒ、Ｒ及びＲ３は、それぞ゛れ前記と同じ意味
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。
（４〉下記構造式（Ｉｃ）
Ｉ
（式中、Ｒ１及びＲ２は、それぞれ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。
■下記構造式（Ｉｄ＞
（式中、Ｒ１及びＲ２は、それぞれ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。FIG. 1 is an infrared absorption spectrum diagram of the cyclobutenedione compound of Example 1, and FIG. 2 is an infrared absorption spectrum diagram of the cyclobutenedione compound of Example 2. (Volunteer to write procedural amendments) January 1986 Director General of the Yuhi Patent Office Kunio Ogawa Office 3-3-5 Akasaka, Minato-ku, Tokyo Name (
549) Fuji Xerox Co., Ltd. Representative Yota Kobayashi 6 Contents of amendment ('I) "2. Scope of Claims" of the specification is amended as shown in the attached sheet. 2. Claims (1) The following general formula (I> ^ (wherein R1, R2 and R3 each represent a methyl group, ethyl group, propyl group or butyl group, and X represents a chlorine atom or a hydroxyl group) ) A cyclobutenedione derivative represented by the following formula (Ia> (wherein, R1, R2 and R3 each have the same meaning as above). Dione derivative. (3) The cyclobutenedione derivative according to claim 1, represented by the following structural formula (Ib> (wherein R, R and R3 each have the same meaning as above) (4) Cyclobutenedione derivative according to claim 1, represented by the following structural formula (Ic) I (wherein R1 and R2 each have the same meaning as above). ■ The following structural formula Cyclobutenedione derivative according to claim 1, represented by (Id> (wherein R1 and R2 each have the same meanings as above).
Claims (4)
基、エチル基、プロピル基又はブチル基を表わし、Ｘは
塩素原子又は水酸基を表わす） で示されるシクロブテンジオン誘導体。(1) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1, R_2 and R_3 each represent a methyl group, ethyl group, propyl group or butyl group, and X is A cyclobutenedione derivative represented by (representing a chlorine atom or a hydroxyl group).
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。(2) Claims represented by the following structural formula (Ia) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(Ia) (In the formula, R_1, R_2 and R_3 each represent the same meaning as above) Cyclobutenedione derivative according to item 1.
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) Claims represented by the following structural formula (I b) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I b) (In the formula, R_1, R_2 and R_3 each represent the same meaning as above) Cyclobutenedione derivative according to item 1.
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。 （４）下記構造式（ I ｄ） ▲数式、化学式、表等があります▼（ I ｄ） （式中、Ｒ＿１及びＲ＿２は、それぞれ前記と同じ意味
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。(4) Claim 1 represented by the following structural formula (Ic) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(Ic) (In the formula, R_1 and R_2 each represent the same meaning as above) Cyclobutenedione derivatives described in Section. (4) Claim 1 represented by the following structural formula (I d) ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ (I d) (In the formula, R_1 and R_2 each represent the same meaning as above) Cyclobutenedione derivatives described in Section.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30586687A JPH0768195B2 (en) | 1987-12-04 | 1987-12-04 | Novel cyclobutenedione derivative |
| US07/278,917 US5047589A (en) | 1987-12-04 | 1988-12-02 | Electrophotographic light-sensitive material containing squarylium compound |
| US07/623,697 US5169987A (en) | 1987-12-04 | 1990-12-07 | Squarlylium compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30586687A JPH0768195B2 (en) | 1987-12-04 | 1987-12-04 | Novel cyclobutenedione derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01146852A true JPH01146852A (en) | 1989-06-08 |
| JPH0768195B2 JPH0768195B2 (en) | 1995-07-26 |
Family
ID=17950297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30586687A Expired - Fee Related JPH0768195B2 (en) | 1987-12-04 | 1987-12-04 | Novel cyclobutenedione derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0768195B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005122320A1 (en) * | 2004-06-09 | 2005-12-22 | Kyowa Hakko Chemical Co., Ltd. | Photoelectric conversion material, photoelectric converter and photoelectrochemical cell |
-
1987
- 1987-12-04 JP JP30586687A patent/JPH0768195B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005122320A1 (en) * | 2004-06-09 | 2005-12-22 | Kyowa Hakko Chemical Co., Ltd. | Photoelectric conversion material, photoelectric converter and photoelectrochemical cell |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0768195B2 (en) | 1995-07-26 |
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