JPH0553836B2 - - Google Patents
Info
- Publication number
- JPH0553836B2 JPH0553836B2 JP25019483A JP25019483A JPH0553836B2 JP H0553836 B2 JPH0553836 B2 JP H0553836B2 JP 25019483 A JP25019483 A JP 25019483A JP 25019483 A JP25019483 A JP 25019483A JP H0553836 B2 JPH0553836 B2 JP H0553836B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- charge
- general formula
- disazo 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.)
- Expired - Lifetime
Links
- -1 disazo compound Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 230000032258 transport Effects 0.000 description 6
- YFBMJEBQWQBRQJ-UHFFFAOYSA-N 4-n-(4-aminophenyl)-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=CC=C1 YFBMJEBQWQBRQJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NGQSLSMAEVWNPU-UHFFFAOYSA-N 1,2-bis(2-phenylethenyl)benzene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1C=CC1=CC=CC=C1 NGQSLSMAEVWNPU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XQEXCGWVXCWUPW-UHFFFAOYSA-N n-[(1-ethyl-9h-carbazol-3-yl)methylideneamino]-n-methylaniline Chemical compound C=1C=2C3=CC=CC=C3NC=2C(CC)=CC=1C=NN(C)C1=CC=CC=C1 XQEXCGWVXCWUPW-UHFFFAOYSA-N 0.000 description 1
- CIPHTOQKGSLCLV-UHFFFAOYSA-N n-phenylnaphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC1=CC=CC=C1 CIPHTOQKGSLCLV-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Landscapes
- Photoreceptors In Electrophotography (AREA)
Description
技術分野
本発明は新規なジスアゾ化合物およびその製造
方法に関する。
従来技術
従来からアゾ化合物が電子写真方式に用いられ
る感光体の電荷発生物質として有効であることが
知られている。この電子写真用感光体は、光によ
つて電荷担体を発生する電荷発生物質と、発生し
た電荷担体を搬送する電荷搬送物質との双方を感
光層に用い、選択的に電荷を散逸して静電潜像を
形成するのに必要な電荷の発生と搬送とを、それ
ぞれ別個の物質に分担させたものである。このよ
うな機能分離型の感光体は、電荷発生物質および
電荷搬送物質の選択の幅が広がり高感度化が可能
であり、しかも可撓性に富み耐久性に優れたもの
である。
電荷発生物質としては、スチリルスチルベン骨
格を有するジスアゾ化合物（特開昭53−133445号
公報）、あるいは、カルバゾール骨格を有するジ
スアゾ化合物（特開昭53−95966号公報）、トリフ
エニルアミン骨格を有するトリスアゾ化合物（特
開昭53−132547号公報）、オキサジアゾール骨格
を有するジスアゾ化合物（特開昭54−12742号公
報）、ジスチリルカルバゾール骨格を有するジス
アゾ化合物（特開昭54−14967号公報）、ビススチ
ルベン骨格を有するジスアゾ化合物（特開昭54−
17733号公報）、ジベンゾチオフエン骨格を有する
ジスアゾ化合物（特開昭54−21728号公報）、フル
オレノン骨格を有するジスアゾ化合物（特開昭54
−22834号公報）などが報告されている。しかし
ながら、これらの電荷発生物質に一長一短がある
のも事実であり、さらに優れた電荷発生物質の開
発がまたれている。
目 的
本発明は、電子写真用感光体の電荷発生物質な
どとして有用なジスアゾ化合物およびその製造方
法を提供することを目的とする。
構 成
本発明の１は、一般式（）
（式中、
Ｙはフエニル基または低級アルキル基、低級ア
ルコキシ基、ハロゲン原子もしくはニトロ基で置
換されたフエニル基を表わし、
Ｚはフエニル核に縮合するベンゼン環もしくは
カルバゾール環を表わす。
で表わされるジスアゾ化合物である。
本発明の他の１は、式（）
で表わされる４，4′−ジアミノトリフエニルアミ
ンをジアゾ化して一般式（）
（式中、Ｘはアニオン官能基を表わす。）
で表わされるテトラゾニウム塩とし、このテトラ
ゾニウム塩と一般式（）
（式中、
Ｙはフエニル基または低級アルキル基、低級ア
ルコキシ基、ハロゲン原子もしくはニトロ基で置
換されたフエニル基を表わし、
Ｚはフエニル核に縮合するベンゼン環もしくは
カルバゾール環を表わす。）
で表わされるカツプラーとを反応させることを特
徴とする一般式（）
（式中、ＹおよびＺは前述の通り。）
で表わされるジスアゾ化合物の製造方法である。
上記一般式（）のＹのフエニル基の置換基の
低級アルキル基としては、メチル基、エチル基な
ど、低級アルコキシ基としては、メトキシ基、エ
トキシ基など、ハロゲン原子としてはフツ素原
子、臭素原子、ヨウ素原子などが挙げられる。
次に本発明のジスアゾ化合物の具体例を示す。
ここで、簡略化のため一般式（）を
と表わし、カツプラー残基Ａのみで示した。
TECHNICAL FIELD The present invention relates to a novel disazo compound and a method for producing the same. Prior Art It has been known that azo compounds are effective as charge-generating substances for photoreceptors used in electrophotography. This electrophotographic photoreceptor uses both a charge-generating material that generates charge carriers when exposed to light and a charge-transporting material that transports the generated charge carriers in the photosensitive layer, and selectively dissipates charges to create a static image. The generation and transport of the charges necessary to form a latent image are assigned to separate substances. Such a functionally separated type photoreceptor has a wide range of choices for charge-generating substances and charge-transporting substances, can achieve high sensitivity, and is highly flexible and has excellent durability. As the charge generating substance, a disazo compound having a styrylstilbene skeleton (Japanese Unexamined Patent Publication No. 133445/1982), a disazo compound having a carbazole skeleton (Japanese Unexamined Patent Publication No. 53-95966), or a trisazo compound having a triphenylamine skeleton can be used. compound (JP-A-53-132547), disazo compound having an oxadiazole skeleton (JP-A-54-12742), disazo compound having a distyrylcarbazole skeleton (JP-A-54-14967), Disazo compound having a bisstilbene skeleton
17733), disazo compounds having a dibenzothiophene skeleton (Japanese Unexamined Patent Application Publication No. 17728), disazo compounds having a fluorenone skeleton (Japanese Unexamined Patent Application Publication No. 1982-21728),
-22834 Publication) etc. have been reported. However, it is true that these charge-generating materials have advantages and disadvantages, and even better charge-generating materials are being developed. Purpose An object of the present invention is to provide a disazo compound useful as a charge generating material for an electrophotographic photoreceptor, and a method for producing the same. Structure 1 of the present invention is the general formula () (In the formula, Y represents a phenyl group, a lower alkyl group, a lower alkoxy group, a phenyl group substituted with a halogen atom or a nitro group, and Z represents a benzene ring or a carbazole ring fused to the phenyl nucleus. The other compound of the present invention is a compound having the formula () By diazotizing 4,4'-diaminotriphenylamine represented by the general formula () (In the formula, X represents an anionic functional group.) A tetrazonium salt represented by this tetrazonium salt and the general formula () (In the formula, Y represents a phenyl group, a lower alkyl group, a lower alkoxy group, a phenyl group substituted with a halogen atom or a nitro group, and Z represents a benzene ring or carbazole ring fused to the phenyl nucleus.) General formula () characterized by reacting with Katsupura (In the formula, Y and Z are as described above.) This is a method for producing a disazo compound represented by: Examples of the lower alkyl group as a substituent for the phenyl group of Y in the above general formula () include methyl group and ethyl group; examples of the lower alkoxy group include methoxy group and ethoxy group; and examples of the halogen atom include fluorine atom and bromine atom. , iodine atom, etc. Next, specific examples of the disazo compound of the present invention will be shown.
Here, for simplicity, the general formula () is , and only the coupler residue A is shown.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
上記のジスアゾ化合物は、４，4′−ジアミノト
リフエニルアミンを出発原料とし、ジアゾ化し、
テトラゾニウム塩とし、ついで適当なカツプラー
との間にカツプリング反応を行なわしめることに
より製造できる。４，4′−ジアミノトリフエニル
アミンは、たとえばRichard Herz，Ber.，23，
2538に記載される方法により製造できる。
４，4′−ジアミノトリフエニルアミンのジアゾ
化は、これを希塩酸あるいは希硫酸のような希薄
無機酸中で亜硝酸ナトリウム水溶液を−10℃ない
し、10℃にて添加することにより行なわれる。こ
のジアゾ化反応は、およそ30分間から３時間で完
結する。さらに反応混合物に、たとえばホウフツ
化水素酸あるいはホウフツ化ナトリウム水溶液な
どを加えてテトラゾニウム塩として沈殿させ、結
晶を取してから次の反応に用いることが望まし
い。次いで、このテトラゾニウム塩に一般式
（）で表わされるカツプラーを作用させてカツ
プリング反応を起させることにより行なわれる。
実際にはこの反応は、Ｎ，Ｎ−ジメチルホルムア
ミド（DMF）やジメチルスルホキシドなどの有
機溶媒にテトラゾニウム塩およびカツプラーを混
合溶解しておき、これに約−10℃ないし40℃にて
酢酸ナトリウム水溶液などのアルカリ水溶液を滴
下することにより行なわれる。この反応はおよそ
５分間ないし３時間で完結する。反応終了後、析
出している結晶を取し、適切な方法により精製
（たとえば水あるいは／および有機溶剤による洗
浄、再結晶法など）することにより上記ジスアゾ
化合物の製造は完了する。
このようにして製造される本発明のジスアゾ化
合物の製造例を示せば次の通りである。
製造例 １
（ジスアゾ化合物No.１の製造）
水10mlと濃塩酸17mlよりなる塩中へ４，4′−ジ
アミノトリフエニルアミン5.51grを加え、室温で
１時間撹拌した後、−２℃まで冷却し、ついで、
これに亜硝酸ナトリウム3.31grを水12mlに溶液を
−２〜１℃の温度で30分間にわたり滴下した。
その後、同温度で１時間30分撹拌した後、微量
の不溶部を除去し、この反応液中に42％硼弗化水
素酸20mlを加え、冷却静置した。生成した赤橙色
針状結晶を別し、エタノールで洗浄したのち乾
燥して、8.55gr（収率90.3％）のテトラゾニウム
ジフルオロボレートを得た。赤外線吸収スペクト
ル（KBr錠剤法）では2230cm-1にN2
に基づく
吸収帯が認められた。
このようにして得られたテトラゾニウム塩
0.95grと、カツプラーとして２−ヒドロキシ−３
−ナフトエ酸アニリド1.26grとを、冷却したＮ，
Ｎ−ジメチルホルムアミド230mlに溶解し、これ
に酢酸ナトリウム0.66grおよび水10mlからなる溶
液を17〜21℃の温度で５分間にわたつて滴下し
た。その後、さらに室温で３時間撹拌した。つい
で、生成した沈殿を取し、Ｎ，Ｎ−ジメチルホ
ルムアミド300mlで５回洗浄し、次に水300mlで２
回洗浄した後、80℃で２mmHgの減圧下に乾燥し
て、前記化合物No.１のジスアゾ化合物1.11gr（収
率67.4％）を得た。
融点 300℃以上
元素分析（％）
Ｃ Ｈ Ｎ
実測値 75.57 4.70 11.76
計算値 75.80 4.53 11.90
また、赤外線吸収スペクトル（KBr錠剤法）
を第１図に示した。
製造例 ２〜16
カツプラーとして表−２に示した化合物を用い
た以外は製造例１と全く同様に操作し、表−２に
示すジスアゾ化合物を製造した。これらのジスア
ゾ化合物についての赤外線吸収スペクトル
（KBr錠剤法）のνc=p（アミド）の吸収融点、元
素分析値も併せて表−２に示した。[Table] The above disazo compound uses 4,4'-diaminotriphenylamine as a starting material, diazotizes it,
It can be produced by forming a tetrazonium salt and then performing a coupling reaction with a suitable coupler. 4,4'-diaminotriphenylamine is described, for example, by Richard Herz, Ber., 23 ,
It can be produced by the method described in 2538. Diazotization of 4,4'-diaminotriphenylamine is carried out by adding an aqueous solution of sodium nitrite in a dilute inorganic acid such as dilute hydrochloric acid or dilute sulfuric acid at -10°C to 10°C. This diazotization reaction is completed in approximately 30 minutes to 3 hours. Furthermore, it is preferable to add, for example, hydroborofluoric acid or an aqueous sodium borofluoride solution to the reaction mixture to precipitate the tetrazonium salt, and use it in the next reaction after crystallizing it. Next, this tetrazonium salt is reacted with a coupler represented by the general formula () to cause a coupling reaction.
In reality, this reaction is carried out by dissolving a tetrazonium salt and a coupler in an organic solvent such as N,N-dimethylformamide (DMF) or dimethyl sulfoxide, and adding aqueous sodium acetate solution to the mixture at about -10°C to 40°C. This is done by dropping an alkaline aqueous solution. This reaction is complete in approximately 5 minutes to 3 hours. After the reaction is completed, the precipitated crystals are collected and purified by an appropriate method (for example, washing with water and/or an organic solvent, recrystallization method, etc.) to complete the production of the disazo compound. Examples of the production of the disazo compound of the present invention produced in this manner are as follows. Production Example 1 (Production of Disazo Compound No. 1) 5.51g of 4,4'-diaminotriphenylamine was added to a salt consisting of 10ml of water and 17ml of concentrated hydrochloric acid, stirred at room temperature for 1 hour, and then cooled to -2°C. Then,
A solution of 3.31 gr of sodium nitrite in 12 ml of water was added dropwise to this solution over 30 minutes at a temperature of -2 to 1°C. Thereafter, after stirring at the same temperature for 1 hour and 30 minutes, a trace amount of insoluble portion was removed, and 20 ml of 42% borofluoric acid was added to the reaction solution, and the mixture was allowed to cool and stand still. The produced red-orange needle crystals were separated, washed with ethanol, and then dried to obtain 8.55 gr (yield: 90.3%) of tetrazonium difluoroborate. In the infrared absorption spectrum (KBr tablet method), an absorption band based on N 2 was observed at 2230 cm -1 . Tetrazonium salt thus obtained
0.95gr and 2-hydroxy-3 as a coupler
- 1.26 gr of naphthoic acid anilide and cooled N,
The mixture was dissolved in 230 ml of N-dimethylformamide, and a solution consisting of 0.66 gr of sodium acetate and 10 ml of water was added dropwise thereto over 5 minutes at a temperature of 17 to 21°C. Thereafter, the mixture was further stirred at room temperature for 3 hours. Then, the formed precipitate was collected, washed five times with 300 ml of N,N-dimethylformamide, and then washed twice with 300 ml of water.
After washing twice, it was dried at 80° C. under a reduced pressure of 2 mmHg to obtain 1.11 gr (yield: 67.4%) of the disazo compound No. 1. Melting point 300℃ or higher Elemental analysis (%) C H N Actual value 75.57 4.70 11.76 Calculated value 75.80 4.53 11.90 Infrared absorption spectrum (KBr tablet method)
is shown in Figure 1. Production Examples 2 to 16 The disazo compounds shown in Table 2 were produced in exactly the same manner as in Production Example 1, except that the compounds shown in Table 2 were used as couplers. Table 2 also shows the absorption melting point of ν c=p (amide) in the infrared absorption spectrum (KBr tablet method) and elemental analysis values for these disazo compounds.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
本発明のジスアゾ化合物は前述の通り、機能分
離型の感光体の電荷発生物質として有用である。
この感光体には、第２図に示すように電荷発生物
質１３を含む電荷発生層１５と、電荷搬送物質を
含む電荷搬送層１７とを積層した感光層１９を導
電性支持体１１上に設けた積層型の感光体；電荷
搬送物質を含む電荷搬送媒体中に電荷発生物質を
含有せしめて感光層とした分散型の感光体などが
ある。本発明のジスアゾ化合物は特に積層型の感
光体における電荷発生物質として有用であり、こ
の点をさらに明らかにするために以下に用途例を
示した。
用途例
ジスアゾ化合物No.46を76重量部、ポリエステル
樹脂（バイロン200株式会社東洋紡績製）のテト
ラヒドロフラン溶液（固形分濃度２％）1260重量
部、およびテトラヒドロフラン3700重量部をボー
ルミル中で粉砕混合し、得られた分散液をアルミ
ニウム蒸着したポリエステルベース（導電性支持
体）のアルミ面上にドクターブレードを用いて塗
布し、自然乾燥して、厚さ約1μmの電荷発生層を
形成した。
この電荷発生層上に、電荷搬送物質として９−
エチルカルバゾール−３−アルデヒド１−メチル
−１−フエニルヒドラゾン２重量部、ポリカーボ
ネート樹脂（パンライトＫ−1300：(株)帝人製）２
重量部およびテトラヒドロフラン16重量部を混合
溶解した溶液をドクターブレードを用いて塗布
し、80℃で２分間、ついで105℃で５分間乾燥し
て厚さ約18μmの電荷搬送層を形成して、第２図
に示した積層型の感光体を作成した。
この感光体について、静電複写紙試験装置（(株)
川口電機製作所製、SP428型）を用いて、−6KV
のコロナ放電を20秒間行なつて負に帯電せしめた
後、20秒間暗所に放置し、その時の表面電位Vpp
(V)を測定し、ついでタングステンランプによつて
その表面が照度4.5ルツクスになるようにして光
を照射しその表面電位がVppの1/2になるまでの
時間（秒）を求め、露光量Ｅ1/2（ルツクス・秒）
を算出した。
その結果
Vpp＝−748V
Ｅ1/2＝1.7ルツクス・秒
であつた。
さらに、本発明の感光体を(株)リコー製複写機リ
コピーＰ−500型に装着して画像出しを10000回繰
り返した。その結果、この感光体は複写プロセス
の繰返しにより変化することなく、鮮明な画像が
得られた。これにより、本発明の感光体が耐久性
においても優れたものであることが理解できるの
であろう。[Table] As mentioned above, the disazo compound of the present invention is useful as a charge generating material for a functionally separated photoreceptor.
As shown in FIG. 2, this photoreceptor is provided with a photosensitive layer 19 on a conductive support 11, which is a stack of a charge generation layer 15 containing a charge generation substance 13 and a charge transport layer 17 containing a charge transport substance. There are laminated type photoreceptors; dispersed type photoreceptors in which a charge generating substance is contained in a charge transporting medium containing a charge transporting substance to form a photosensitive layer. The disazo compound of the present invention is particularly useful as a charge generating material in a laminated photoreceptor, and to further clarify this point, application examples are shown below. Application example: 76 parts by weight of disazo compound No. 46, 1260 parts by weight of a tetrahydrofuran solution (solid content concentration 2%) of polyester resin (Byron 200 manufactured by Toyobo Co., Ltd.), and 3700 parts by weight of tetrahydrofuran are ground and mixed in a ball mill. The resulting dispersion was applied onto the aluminum surface of a polyester base (conductive support) on which aluminum was vapor-deposited using a doctor blade, and air-dried to form a charge generation layer with a thickness of approximately 1 μm. On this charge generation layer, 9-
2 parts by weight of ethylcarbazole-3-aldehyde 1-methyl-1-phenylhydrazone, 2 parts of polycarbonate resin (Panlite K-1300: manufactured by Teijin Ltd.)
A solution prepared by mixing and dissolving 16 parts by weight of Tetrahydrofuran and 16 parts by weight of tetrahydrofuran was applied using a doctor blade, and dried at 80°C for 2 minutes and then at 105°C for 5 minutes to form a charge transport layer with a thickness of about 18 μm. A laminated photoreceptor shown in Figure 2 was prepared. Regarding this photoreceptor, electrostatic copying paper testing equipment (Co., Ltd.)
-6KV using Kawaguchi Electric Seisakusho, SP428 type)
After performing corona discharge for 20 seconds to make it negatively charged, it was left in a dark place for 20 seconds, and the surface potential at that time, V pp
(V), then irradiate the surface with light using a tungsten lamp at an illuminance of 4.5 lux, find the time (seconds) until the surface potential becomes 1/2 of Vpp , and then expose Quantity E1/2 (lux/second)
was calculated. As a result, Vpp = -748V E1/2 = 1.7 Lux·sec. Further, the photoreceptor of the present invention was installed in a copying machine model Ricopy P-500 manufactured by Ricoh Co., Ltd., and image production was repeated 10,000 times. As a result, this photoreceptor did not change due to repeated copying processes, and clear images were obtained. From this, it can be understood that the photoreceptor of the present invention is also excellent in durability.
第１図は本発明に用いるジスアゾ顔料No.１の赤
外線吸収スペクトル（KBr錠剤法）である。第
２図は本発明のジスアゾ化合物を用いた感光体の
構成例を示す拡大断面図である。
１１…導電性支持体、１３…ジスアゾ化合物、
１５…電荷発生層、１７…電荷搬送層、１９…感
光層。
FIG. 1 shows an infrared absorption spectrum (KBr tablet method) of disazo pigment No. 1 used in the present invention. FIG. 2 is an enlarged sectional view showing an example of the structure of a photoreceptor using the disazo compound of the present invention. 11... Conductive support, 13... Disazo compound,
15... Charge generation layer, 17... Charge transport layer, 19... Photosensitive layer.
Claims (1)
基、低級アルコキシ基、ハロゲン原子もしくはニ
トロ基で置換されたフエニル基を表わし、 Ｚはフエニル核に縮合するベンゼン環もしくは
カルバゾール環を表わす。） で表わされるジスアゾ化合物。 ２ 式 で表わされる４，４−ジアミノトリフエニルアミ
ンをジスアゾ化して一般式（） （式中、Ｘはアニオン官能基を表わす。） で表わされるテトラゾニウム塩とし、このテトラ
ゾニウム塩と一般式（） （式中、 Ｙはフエニル基または低級アルキル基、低級ア
ルコキシ基、ハロゲン原子もしくはニトロ基で置
換されたフエニル基を表わし、 Ｚはフエニル核に縮合するベンゼン環もしくは
カルバゾール環を表わす。） で表わされるカツプラーとを反応させることを特
徴とする一般式（） （式中、ＹおよびＺは前述の通り。） で表わされるジスアゾ化合物の製造方法。[Claims] 1. General formula (In the formula, Y represents an unsubstituted phenyl group or a lower alkyl group, a lower alkoxy group, a phenyl group substituted with a halogen atom or a nitro group, and Z represents a benzene ring or carbazole ring fused to the phenyl nucleus.) A disazo compound represented by 2 formulas By disazotizing 4,4-diaminotriphenylamine represented by the general formula () (In the formula, X represents an anionic functional group.) A tetrazonium salt represented by this tetrazonium salt and the general formula () (In the formula, Y represents a phenyl group, a lower alkyl group, a lower alkoxy group, a phenyl group substituted with a halogen atom or a nitro group, and Z represents a benzene ring or carbazole ring fused to the phenyl nucleus.) General formula () characterized by reacting with Katsupura (In the formula, Y and Z are as described above.) A method for producing a disazo compound represented by:
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25019483A JPS60141764A (en) | 1983-12-28 | 1983-12-28 | Novel disazo compound and its production |
| DE3447685A DE3447685A1 (en) | 1983-12-28 | 1984-12-28 | DISAZO CONNECTIONS, METHOD FOR THEIR PRODUCTION AND AN ELECTROPHOTOGRAPHIC ELEMENT CONTAINING THESE CONNECTIONS |
| GB08432740A GB2153378B (en) | 1983-12-28 | 1984-12-28 | Disazo compounds and electrophotographic elements containing them |
| US06/687,111 US4582771A (en) | 1983-12-28 | 1984-12-28 | Disazo compound, method for preparing the same, and electrophotographic element containing the same for use in electrophotography |
| US06/756,468 US4663442A (en) | 1983-12-28 | 1985-07-18 | Disazo triphenylamine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25019483A JPS60141764A (en) | 1983-12-28 | 1983-12-28 | Novel disazo compound and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60141764A JPS60141764A (en) | 1985-07-26 |
| JPH0553836B2 true JPH0553836B2 (en) | 1993-08-11 |
Family
ID=17204211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25019483A Granted JPS60141764A (en) | 1983-12-28 | 1983-12-28 | Novel disazo compound and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60141764A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07113222B2 (en) * | 1991-12-18 | 1995-12-06 | 株木建設株式会社 | Dredging vessel and dredging method by dredging vessel |
| JP3563916B2 (en) * | 1996-04-26 | 2004-09-08 | キヤノン株式会社 | Electrophotographic photoreceptor, electrophotographic apparatus and process cartridge using the electrophotographic photoreceptor |
-
1983
- 1983-12-28 JP JP25019483A patent/JPS60141764A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60141764A (en) | 1985-07-26 |
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