JPH0761954A - Pyrenylamine compound and its production - Google Patents
Pyrenylamine compound and its productionInfo
- Publication number
- JPH0761954A JPH0761954A JP15426094A JP15426094A JPH0761954A JP H0761954 A JPH0761954 A JP H0761954A JP 15426094 A JP15426094 A JP 15426094A JP 15426094 A JP15426094 A JP 15426094A JP H0761954 A JPH0761954 A JP H0761954A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- unsubstituted
- pyrenylamine
- compound
- 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
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、電子写真用の有機光導
電性素材及び蛍光増白剤、特に電子写真用の有機光導電
性材料として有用である、新規なピレニルアミン化合物
及びその製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel pyrenylamine compound useful as an organic photoconductive material for electrophotography and a fluorescent whitening agent, particularly as an organic photoconductive material for electrophotography, and a method for producing the same. .
【０００２】[0002]
【従来の技術】従来、電子写真方式において使用される
感光体の有機光導電性素材としてポリ−Ｎ−ビニルカル
バゾールをはじめ数多くの材料が提案されている。ここ
にいう「電子写真方式」とは一般に光導電性の感光体
を、まず暗所で例えばコロナ放電などにより帯電せし
め、ついで露光部のみの電荷を選択的に放電させること
により静電潜像を得て、この潜像部をトナーなどを用い
た現像手段で可視化して画像を形成するようにした画像
形成法を一つである。このような電子写真方式における
感光体に要求される基本的な特性としては、１）暗所に
おいて適当な電位に帯電されること、２）暗所における
電荷の放電が少ないこと、３）光照射により速やかに電
荷を放電すること、などが挙げられる。しかし従来の光
導電性有機材料はこれらの要求をかならずしも十分に満
足していないのが実状である。2. Description of the Related Art Conventionally, many materials such as poly-N-vinylcarbazole have been proposed as organic photoconductive materials for photoconductors used in electrophotography. The term "electrophotographic method" generally means that a photoconductive photoconductor is first charged in a dark place by, for example, corona discharge, and then an electrostatic latent image is formed by selectively discharging electric charges only in an exposed portion. One is an image forming method in which the latent image portion is visualized by a developing means using toner or the like to form an image. The basic characteristics required for a photoreceptor in such an electrophotographic system are as follows: 1) being charged to an appropriate potential in a dark place, 2) little discharge of charges in a dark place, and 3) irradiation with light. To discharge the electric charges more quickly. However, the conventional photoconductive organic material does not always satisfy these requirements.
【０００３】一方、セレンや酸化亜鉛は光導電性無機材
料として知られており、中でもセレンは広く実用に供さ
れていることは事実である。しかし最近電子写真のプロ
セスの点から、感光体に対する種々の要求、すなわち一
例として前述の基本的特性に加えて、例えばその形状に
ついても可撓性のあるベルト状の感光体などが要求され
るようになってきている。しかしセレンの場合は一般に
このような形状のものに作成することは困難である。On the other hand, selenium and zinc oxide are known as photoconductive inorganic materials, and it is true that selenium is widely used in practice. However, recently, from the viewpoint of electrophotographic process, various requirements for the photoreceptor, that is, for example, in addition to the basic characteristics described above, a belt-shaped photoreceptor having a flexible shape is required. Is becoming. However, in the case of selenium, it is generally difficult to make such a shape.
【０００４】近年、これらの無機物質の欠点を排除する
ためにいろいろな有機物質を用いた電子写真用感光体を
提案され、実用に供されているものもある。例えば、ス
チルベン誘導体（特開昭５８−１９８４２５号、特開昭
５８−１８９１４５号）やトリアリールアミン誘導体
（特開昭５８−６５４４０号）などが挙げられるが、未
だ充分に満足するものが得られていないのが実状であ
る。In recent years, in order to eliminate the drawbacks of these inorganic substances, electrophotographic photoreceptors using various organic substances have been proposed and some have been put to practical use. Examples thereof include stilbene derivatives (JP-A-58-198425 and JP-A-58-189145) and triarylamine derivatives (JP-A-58-65440), but those which are still sufficiently satisfactory are obtained. The reality is that they do not.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、従来の感光
体に於ける光導電性素材のもつ欠点を除去した、殊に電
子写真用の光導電性素材として有用な新規なピレニルア
ミン化合物及びその製造方法を提供することを目的とす
る。DISCLOSURE OF THE INVENTION The present invention eliminates the disadvantages of the photoconductive materials in conventional photoconductors, and is a novel pyrenylamine compound useful as a photoconductive material for electrophotography, and a novel pyrenylamine compound thereof. It is intended to provide a manufacturing method.
【０００６】[0006]
【課題を解決するための手段】本発明によれば、下記一
般式（Ｉ）（化１）で表される不飽和結合を有するピレ
ニルアミン化合物According to the present invention, a pyrenylamine compound having an unsaturated bond represented by the following general formula (I) (Formula 1)
【化１】 （式中、Ｒ1はハロゲン原子、置換もしくは無置換のア
ルキル基、置換もしくは無置換のアルコキシ基、置換も
しくは無置換のフェニル基を表し、同一でも異なってい
てもよい。Ｒ2は水素原子、アルコキシカルボニル基、
置換もしくは無置換のアルキル基、又は置換もしくは無
置換のフェニル基を表す。Ｗは水素原子、置換もしくは
無置換のアルキル基、フェニルチオ基、鎖状不飽和炭化
水素からなる２価の基、置換もしくは無置換の炭素環式
芳香族基の１価もしくは２価の基、置換もしくは無置換
の複素環からなる１価もしくは２価の基を表す。ｌは０
〜５、ｍは０または１、ｎは１または２の整数を表わ
す。）が提供され、また、下記一般式（II）（化２）で
表わされるピレニルアミン化合物を還元することを特徴
とする下記一般式（化１）で表わされるピレニルアミン
化合物が提供される。[Chemical 1] (In the formula, R 1 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different. R 2 is a hydrogen atom, An alkoxycarbonyl group,
It represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, a phenylthio group, a divalent group consisting of a chain unsaturated hydrocarbon, a monovalent or divalent group of a substituted or unsubstituted carbocyclic aromatic group, or a substituted group. Alternatively, it represents a monovalent or divalent group consisting of an unsubstituted heterocycle. l is 0
˜5, m is 0 or 1, and n is an integer of 1 or 2. ) Is also provided, and a pyrenylamine compound represented by the following general formula (Formula 1) is provided, which is characterized by reducing the pyrenylamine compound represented by the following general formula (II) (Formula 2).
【化２】 （式中、Ｒ1はハロゲン原子、置換もしくは無置換のア
ルキル基、置換もしくは無置換のアルコキシ基、置換も
しくは無置換のフェニル基を表し、同一でも異なってい
てもよい。Ｒ2は水素原子、アルコキシカルボニル基、
置換もしくは無置換のアルキル基、又は置換もしくは無
置換のフェニル基を表す。Ｗは水素原子、置換もしくは
無置換のアルキル基、フェニルチオ基、鎖状不飽和炭化
水素からなる２価の基、置換もしくは無置換の炭素環式
芳香族基の１価もしくは２価の基、置換もしくは無置換
の複素環からなる１価もしくは２価の基を表す。ｌは０
〜５、ｍは０または１、ｎは１または２の整数を表わ
す。）[Chemical 2] (In the formula, R 1 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different. R 2 is a hydrogen atom, An alkoxycarbonyl group,
It represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, a phenylthio group, a divalent group consisting of a chain unsaturated hydrocarbon, a monovalent or divalent group of a substituted or unsubstituted carbocyclic aromatic group, or a substituted group. Alternatively, it represents a monovalent or divalent group consisting of an unsubstituted heterocycle. l is 0
˜5, m is 0 or 1, and n is an integer of 1 or 2. )
【化１】 （式中、Ｒ1はハロゲン原子、置換もしくは無置換のア
ルキル基、置換もしくは無置換のアルコキシ基、置換も
しくは無置換のフェニル基を表し、同一でも異なってい
てもよい。Ｒ2は水素原子、アルコキシカルボニル基、
置換もしくは無置換のアルキル基、又は置換もしくは無
置換のフェニル基を表す。Ｗは水素原子、置換もしくは
無置換のアルキル基、フェニルチオ基、鎖状不飽和炭化
水素からなる２価の基、置換もしくは無置換の炭素環式
芳香族基の１価もしくは２価の基、置換もしくは無置換
の複素環からなる１価もしくは２価の基を表す。ｌは０
〜５、ｍは０または１、ｎは１または２の整数を表わ
す。）[Chemical 1] (In the formula, R 1 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different. R 2 is a hydrogen atom, An alkoxycarbonyl group,
It represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, a phenylthio group, a divalent group consisting of a chain unsaturated hydrocarbon, a monovalent or divalent group of a substituted or unsubstituted carbocyclic aromatic group, or a substituted group. Alternatively, it represents a monovalent or divalent group consisting of an unsubstituted heterocycle. l is 0
˜5, m is 0 or 1, and n is an integer of 1 or 2. )
【０００７】本発明に係る前記一般式（Ｉ）で表わされ
るピレニルアミン化合物は新規物質であり、前記一般式
（II）で表わされる不飽和結合を有するピレニルアミン
化合物を還元することによって製造される。具体的に
は、前記一般式（II）で表わされる不飽和結合を有する
ピレニルアミン化合物から前記化１で表わされるピレニ
ルアミン化合物を得るための還元反応として、例えば、
水素添加法を挙げることができる。この反応は、例えば
反応系を密閉系とし、気相部を１気圧の水素ガスで置換
して、触媒の存在下、激しく撹拌もしくは振動すること
により行なわれる。吸収された量に応じて水素ガスが供
給される減圧弁を介して、水素ガスを供給する。理論量
の水素ガスを吸収した時点で吸収が停止するので、反応
終了とする。この場合、反応温度は室温でよいが、水素
ガスの吸収が遅い場合は加温してもよい。また反応溶媒
には、メタノール、エタノール、プロパノール、テトラ
ヒドロフラン、ジオキサン、酢酸エチル、Ｎ，Ｎ−ジメ
チルホルムアミドなどを使用することができる。また、
触媒としては、二酸化白金、ラネーニッケル、あるいは
活性炭、アルミナ若しくは硫酸バリウムなどに担持され
た白金、パラジウム、ロジウム若しくはルテニウムなど
が使用される。The pyrenylamine compound represented by the general formula (I) according to the present invention is a novel substance, and is produced by reducing the pyrenylamine compound having an unsaturated bond represented by the general formula (II). Specifically, as the reduction reaction for obtaining the pyrenylamine compound represented by the above chemical formula 1 from the pyrenylamine compound having an unsaturated bond represented by the general formula (II), for example,
A hydrogenation method can be mentioned. This reaction is carried out, for example, by making the reaction system a closed system, substituting the gas phase part with hydrogen gas at 1 atm, and vigorously stirring or vibrating in the presence of a catalyst. Hydrogen gas is supplied through a pressure reducing valve to which hydrogen gas is supplied according to the absorbed amount. Since the absorption stops when the theoretical amount of hydrogen gas is absorbed, the reaction is terminated. In this case, the reaction temperature may be room temperature, but may be heated if hydrogen gas absorption is slow. As the reaction solvent, methanol, ethanol, propanol, tetrahydrofuran, dioxane, ethyl acetate, N, N-dimethylformamide or the like can be used. Also,
As the catalyst, platinum dioxide, Raney nickel, or platinum supported on activated carbon, alumina, barium sulfate, or the like, palladium, rhodium, ruthenium, or the like is used.
【０００８】このようにして得られる本発明の前記一般
式（Ｉ）（化１）で表わされるピレニルアミン化合物の
具体例を以下の表１に例示する。Specific examples of the pyrenylamine compound represented by the above general formula (I) (Formula 1) of the present invention thus obtained are shown in Table 1 below.
【表１−（１）】 [Table 1- (1)]
【０００９】[0009]
【表１−（２）】 [Table 1- (2)]
【００１０】[0010]
【表２】 [Table 2]
【００１１】[0011]
【表３】 [Table 3]
【００１２】[0012]
【表４】 [Table 4]
【００１３】[0013]
【表５】 [Table 5]
【００１４】本発明にかかわる新規なピレニルアミン化
合物は、電子写真用感光体に於ける光導電性素材として
きわめて有用であり、染料やルイス酸などの増感剤によ
って光学的あるいは化学的に増感される。また有機顔料
ある今は無機顔料を電荷発生物質とするいわゆる機能力
離型感光体に於ける電荷移動物質としてとりわけ有用で
ある。The novel pyrenylamine compound according to the present invention is extremely useful as a photoconductive material in an electrophotographic photoreceptor and is optically or chemically sensitized by a sensitizer such as a dye or a Lewis acid. It In addition, organic pigments are now particularly useful as charge transfer substances in so-called functional force release type photoconductors which use inorganic pigments as charge generating substances.
【００１５】前記増感剤として例えばメチルバイオレッ
ト、クリスタルバイオレット等のトリアリルメタン染
料、ローズベンガル、エリスロシン、ローダミンＢ等の
キサンテン染料、メチレンブルー等のチアジン染料、
２，４，７−トリニトロ−９−フルオレノン、２，４−
ジニトロ−９−フルオレノンが挙げられる。また有機顔
料としては、シーアイピグメントブルー２５（Ｃ．ｌ．
Ｎｏ．２１１８０）、シーアイピグメントレッド４１
（Ｃ．ｌ．Ｎｏ．２１２００）、シーアイベージックレ
ッド３（Ｃ．１．Ｎｏ．４５２１０）等のアゾ系顔料、
シーアイピグメントブルー１６（Ｃ．ｌ．Ｎｏ．７４１
００）等のフタロシアニン系顔料、シーアイバットブラ
ウン５（Ｃ．ｌ．Ｎｏ．７３４１０）、シーアイバット
ダイ（Ｃ．ｌ．Ｎｏ．７３０３０）等のインジゴ系顔
料、アルゴスカーレットＢ、インダンスレンスカーレッ
トＲ等のペリレン系顔料が挙げられる。また、セレン、
セレン−テルル、硫化カドミウム、α−シリコン等の無
機顔料も使用できる。Examples of the sensitizer include triallylmethane dyes such as methyl violet and crystal violet, xanthene dyes such as rose bengal, erythrosine and rhodamine B, and thiazine dyes such as methylene blue.
2,4,7-trinitro-9-fluorenone, 2,4-
Dinitro-9-fluorenone may be mentioned. As an organic pigment, CI Pigment Blue 25 (Cl.
No. 21180), CI Pigment Red 41
(C.I. No. 21200), C-I Basic Red 3 (C.1. No. 45210), and other azo pigments,
CI Pigment Blue 16 (Cl. No. 741
00) and the like, indigo pigments such as CAIBAT BROWN 5 (C.I.No. 73410) and CIABAT Die (C.I.No. 73030), Argos Scarlet B, Indanth Scarlet R, etc. Perylene pigments. Also, selenium,
Inorganic pigments such as selenium-tellurium, cadmium sulfide and α-silicon can also be used.
【００１６】[0016]
実施例１ １，４−ビス［Ｎ−（１−ピレニル）−Ｎ−（４−メチ
ルフェニル）−４−アミノスチリル］ベンゼン１．０１
ｇ（１．１３ｍｍｏｌ）と５％パラジウム−炭素０．２
０ｇをＴＨＦ３００ｍｌに加え、水素気流下、室温で４
０時間撹拌した。この反応液をセライトで濾過、溶媒を
留去し、シリカゲルカラムクロマト処理（溶離液；トル
エン／シクロヘキサン：２／３ｖｏｌ）を２回行ない精
製物０．８１ｇ（収率８０．２％）を得た。これをトル
エン−エタノール混合溶媒で再結晶して白黄色針状晶の
１，４−ビス［Ｎ−（１−ピレニル）−Ｎ−（４−メチ
ルフェニル）−４−アミノスチリル］ベンゼン０．７６
ｇ（７５．２％）を得た。融点は２３５．５〜２３９．
０℃、元素分析値はＣ60Ｈ52Ｎ2として下記のとおりで
あった。 また、赤外線吸収スペクトル（ＫＢｒ錠剤法）を図１に
示した。Example 1 1,4-bis [N- (1-pyrenyl) -N- (4-methylphenyl) -4-aminostyryl] benzene 1.01
g (1.13 mmol) and 5% palladium-carbon 0.2
Add 0 g to 300 ml of THF and add 4 at room temperature under hydrogen flow.
Stir for 0 hours. The reaction solution was filtered through Celite, the solvent was distilled off, and silica gel column chromatography treatment (eluent: toluene / cyclohexane: 2/3 vol) was performed twice to obtain 0.81 g of a purified product (yield 80.2%). . This was recrystallized with a toluene-ethanol mixed solvent to give 1,4-bis [N- (1-pyrenyl) -N- (4-methylphenyl) -4-aminostyryl] benzene 0.76 as white yellow needle crystals.
g (75.2%) were obtained. The melting point is 235.5-239.
At 0 ° C., the elemental analysis value was as follows for C 60 H 52 N 2 . The infrared absorption spectrum (KBr tablet method) is shown in FIG.
【００１７】実施例２〜６ 実施例１と同様に操作をし、本発明のピレニルアミン化
合物を得た。結果を表６に示す。Examples 2 to 6 The same operation as in Example 1 was carried out to obtain the pyrenylamine compound of the present invention. The results are shown in Table 6.
【００１８】[0018]
【表６】 [Table 6]
【００１９】[0019]
【発明の効果】本発明の前記一般式（化１）で表わされ
るピレニルアミン化合物は、新規であって、電子写真用
の有機光導電性素材、蛍光増白剤として有用であり、特
に電子写真用の有機光導電性材料として用いた場合、感
光体に必要な基本的特定を十分満足しており、また可撓
性の感光体等を作成することができる。INDUSTRIAL APPLICABILITY The pyrenylamine compound represented by the above general formula (Formula 1) of the present invention is novel and useful as an organic photoconductive material for electrophotography and as a fluorescent whitening agent, and particularly for electrophotography. When it is used as the organic photoconductive material, the basic specifications necessary for the photoconductor are sufficiently satisfied, and a flexible photoconductor or the like can be prepared.
【図１】実施例１で得られたピレニルアミン化合物の赤
外線吸収スペクトル図（ＫＢｒ錠剤法）。FIG. 1 is an infrared absorption spectrum diagram (KBr tablet method) of the pyrenylamine compound obtained in Example 1.
【図２】実施例２得られたピレニルアミン化合物の赤外
線吸収スペクトル図（ＫＢｒ錠剤法）。FIG. 2 is an infrared absorption spectrum diagram (KBr tablet method) of the obtained pyrenylamine compound.
【図３】実施例３で得られたピレニルアミン化合物の赤
外線吸収スペクトル図（ＫＢｒ錠剤法）。FIG. 3 is an infrared absorption spectrum diagram (KBr tablet method) of the pyrenylamine compound obtained in Example 3.
【図４】実施例４得られたピレニルアミン化合物の赤外
線吸収スペクトル図（ＫＢｒ錠剤法）。FIG. 4 is an infrared absorption spectrum diagram (KBr tablet method) of the resulting pyrenylamine compound.
【図５】実施例５で得られたピレニルアミン化合物の赤
外線吸収スペクトル図（ＫＢｒ錠剤法）。FIG. 5 is an infrared absorption spectrum diagram (KBr tablet method) of the pyrenylamine compound obtained in Example 5.
【図６】実施例６得られたピレニルアミン化合物の赤外
線吸収スペクトル図（ＫＢｒ錠剤法）。FIG. 6 is an infrared absorption spectrum diagram (KBr tablet method) of the obtained pyrenylamine compound.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 319/20 323/25 7419−4Ｈ Ｇ０３Ｇ 5/06 ３１４ Ｚ 5/08 // Ｃ０７Ｂ 61/00 ３００ (72)発明者 有賀 保 東京都大田区中馬込１丁目３番６号 株式 会社リコー内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location C07C 319/20 323/25 7419-4H G03G 5/06 314 Z 5/08 // C07B 61/00 300 (72) Inventor Tamotsu Ariga 1-3-6 Nakamagome, Ota-ku, Tokyo Within Ricoh Co., Ltd.
Claims (2)
ピレニルアミン化合物。 【化１】 （式中、Ｒ1はハロゲン原子、置換もしくは無置換のア
ルキル基、置換もしくは無置換のアルコキシ基、置換も
しくは無置換のフェニル基を表し、同一でも異なってい
てもよい。Ｒ2は水素原子、アルコキシカルボニル基、
置換もしくは無置換のアルキル基、又は置換もしくは無
置換のフェニル基を表す。Ｗは水素原子、置換もしくは
無置換のアルキル基、フェニルチオ基、鎖状不飽和炭化
水素からなる２価の基、置換もしくは無置換の炭素環式
芳香族基の１価もしくは２価の基、置換もしくは無置換
の複素環からなる１価もしくは２価の基を表す。ｌは０
〜５、ｍは０または１、ｎは１または２の整数を表わ
す。）1. A pyrenylamine compound represented by the following general formula (I) (Formula 1). [Chemical 1] (In the formula, R 1 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different. R 2 is a hydrogen atom, An alkoxycarbonyl group,
It represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, a phenylthio group, a divalent group consisting of a chain unsaturated hydrocarbon, a monovalent or divalent group of a substituted or unsubstituted carbocyclic aromatic group, or a substituted group. Alternatively, it represents a monovalent or divalent group consisting of an unsubstituted heterocycle. l is 0
˜5, m is 0 or 1, and n is an integer of 1 or 2. )
ピレニルアミン化合物を還元することを特徴とする下記
一般式（Ｉ）（化１）で表わされるピレニルアミン化合
物の製造方法。 【化２】 （式中、Ｒ1はハロゲン原子、置換もしくは無置換のア
ルキル基、置換もしくは無置換のアルコキシ基、置換も
しくは無置換のフェニル基を表し、同一でも異なってい
てもよい。Ｒ2は水素原子、アルコキシカルボニル基、
置換もしくは無置換のアルキル基、又は置換もしくは無
置換のフェニル基を表す。Ｗは水素原子、置換もしくは
無置換のアルキル基、フェニルチオ基、鎖状不飽和炭化
水素からなる２価の基、置換もしくは無置換の炭素環式
芳香族基の１価もしくは２価の基、置換もしくは無置換
の複素環からなる１価もしくは２価の基を表す。ｌは０
〜５、ｍは０または１、ｎは１または２の整数を表わ
す。） 【化１】 （式中、Ｒ1はハロゲン原子、置換もしくは無置換のア
ルキル基、置換もしくは無置換のアルコキシ基、置換も
しくは無置換のフェニル基を表し、同一でも異なってい
てもよい。Ｒ2は水素原子、アルコキシカルボニル基、
置換もしくは無置換のアルキル基、又は置換もしくは無
置換のフェニル基を表す。Ｗは水素原子、置換もしくは
無置換のアルキル基、フェニルチオ基、鎖状不飽和炭化
水素からなる２価の基、置換もしくは無置換の炭素環式
芳香族基の１価もしくは２価の基、置換もしくは無置換
の複素環からなる１価もしくは２価の基を表す。ｌは０
〜５、ｍは０または１、ｎは１または２の整数を表わ
す。）2. A method for producing a pyrenylamine compound represented by the following general formula (I) (chemical formula 1), which comprises reducing a pyrenylamine compound represented by the following general formula (II) (chemical formula 2). [Chemical 2] (In the formula, R 1 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different. R 2 is a hydrogen atom, An alkoxycarbonyl group,
It represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, a phenylthio group, a divalent group consisting of a chain unsaturated hydrocarbon, a monovalent or divalent group of a substituted or unsubstituted carbocyclic aromatic group, or a substituted group. Alternatively, it represents a monovalent or divalent group consisting of an unsubstituted heterocycle. l is 0
˜5, m is 0 or 1, and n is an integer of 1 or 2. ) [Chemical 1] (In the formula, R 1 represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenyl group, which may be the same or different. R 2 is a hydrogen atom, An alkoxycarbonyl group,
It represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group. W is a hydrogen atom, a substituted or unsubstituted alkyl group, a phenylthio group, a divalent group consisting of a chain unsaturated hydrocarbon, a monovalent or divalent group of a substituted or unsubstituted carbocyclic aromatic group, or a substituted group. Alternatively, it represents a monovalent or divalent group consisting of an unsubstituted heterocycle. l is 0
˜5, m is 0 or 1, and n is an integer of 1 or 2. )
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|---|---|---|---|
| JP15426094A JP3540015B2 (en) | 1993-06-15 | 1994-06-13 | Pyrenylamine compound and method for producing the same |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5-168521 | 1993-06-15 | ||
| JP16852193 | 1993-06-15 | ||
| JP15426094A JP3540015B2 (en) | 1993-06-15 | 1994-06-13 | Pyrenylamine compound and method for producing the same |
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| Publication Number | Publication Date |
|---|---|
| JPH0761954A true JPH0761954A (en) | 1995-03-07 |
| JP3540015B2 JP3540015B2 (en) | 2004-07-07 |
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ID=26482598
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15426094A Expired - Fee Related JP3540015B2 (en) | 1993-06-15 | 1994-06-13 | Pyrenylamine compound and method for producing the same |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495536B1 (en) | 1999-08-24 | 2002-12-17 | Kao Corporation | Fat or oil composition |
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1994
- 1994-06-13 JP JP15426094A patent/JP3540015B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495536B1 (en) | 1999-08-24 | 2002-12-17 | Kao Corporation | Fat or oil composition |
| US7514472B2 (en) | 1999-08-24 | 2009-04-07 | Kao Corporation | Fat or oil composition |
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| Publication number | Publication date |
|---|---|
| JP3540015B2 (en) | 2004-07-07 |
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