Polycyclo Ring System Having The Hetero Ring As One Of The Cyclo Systems Patents (Class 430/78)
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Patent number: 5622799Abstract: An electrophotographic photosensitive member, a process cartridge having the electrophotographic photosensitive member and an electrophotographic apparatus are provided. The electrophotographic photosensitive member has a conductive substrate and a photosensitive layer thereon, wherein the photosensitive layer contains a disazo pigment represented by the following formula (1): ##STR1## wherein R.sub.1 to R.sub.8 are the same or different and are each a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group, n is a positive integer, A.sub.1 and A.sub.2 are the same or different and are each a coupler residual group having a phenolic hydroxyl group, and at least one of A.sub.1 and A.sub.2 is a coupler residual group represented by the following formula (2): ##STR2## wherein X.sub.1 is a residual group forming a polycyclic aromatic ring or a heterocyclic ring by condensing with a benzene ring, R.sub.9 and R.sub.Type: GrantFiled: November 21, 1994Date of Patent: April 22, 1997Assignee: Canon Kabushiki KaishaInventors: Koichi Suzuki, Hideyuki Takai, Satomi Sugiyama, Mitsuhiro Kunieda
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Patent number: 5616441Abstract: According to the present invention, there is provided a novel tryptoanthorine derivative represented by the formula: ##STR1## wherein R.sup.1a, R.sup.1b, R.sup.1c, R.sup.1d, R.sup.2a, R.sup.2b, R.sup.2c, and R.sup.2d are the same or different and indicate a hydrogen atom, an alkyl group or a halogenated alkyl group; provided that R.sup.1a, R.sup.1b, R.sub.1c and R.sup.1d do not indicate a hydrogen atom, simultaneously. Tryptoanthorine and a derivative thereof are suitably used for an electrophotosensitive material because of their excellent electron transferring capability.Type: GrantFiled: September 13, 1995Date of Patent: April 1, 1997Assignee: Mita Industrial Co., Ltd.Inventors: Hirofumi Kawaguchi, Yasufumi Mizuta, Syunichi Matsumoto, Nobuko Akiba, Toshiyuki Fukami, Ichiro Yamazato, Hisakazu Uegaito, Yuji Tanaka
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Patent number: 5614342Abstract: Cocrystallized titanyl phthalocyanine-titanyl fluorophthalocyanine compositions, preparation methods, and electrophotographic elements utilizing the compositions. The method has the steps of: admixing crude titanyl phthalocyanine and crude titanyl fluorophthalocyanine to provide a pigment mixture; increasing the amorphousness of the pigment mixture as determined by X-ray crystallography using X-radiation characteristic of Cu K.alpha. at a wavelength of 1.541 .ANG. of the Bragg angle 2.theta. to provide an amorphous pigment mixture; contacting the amorphous pigment mixture with organic solvent having a gamma.sub.c hydrogen bonding parameter of less than 8.0; and prior to the contacting, substantially excluding the amorphous pigment mixture from contact with organic solvent having a gamma.sub.c hydrogen bonding parameter greater than 9.0.Type: GrantFiled: May 2, 1995Date of Patent: March 25, 1997Assignee: Eastman Kodak CompanyInventors: Michel F. Molaire, Jeanne E. Kaeding
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Patent number: 5604065Abstract: An electrophotographic photoconductor includes an electroconductive substrate, and a photoconductive layer formed thereon containing at least one tertiary amine compound of formula (I) as an effective component: ##STR1## wherein Ar.sup.1 and Ar.sup.3 each is an aryl group which may have a substituent; Ar.sup.2 is a bivalent group of a carbocyclic aromatic compound or a bivalent group of a heterocyclic compound; R.sup.1 is a hydrogen atom, an alkyl group which may have a substituent or an alkoxyl group which may have a substituent; and R.sup.2 is a hydrogen atom, an alkyl group which may have a substituent or an aryl group which may have a substituent. A novel triphenylamine compound for use in the electrophotographic photoconductor is provided.Type: GrantFiled: September 14, 1995Date of Patent: February 18, 1997Assignees: Ricoh Company, Ltd., Hodogaya Chemical Co., Ltd.Inventors: Tomoyuki Shimada, Masaomi Sasaki, Tamotsu Aruga, Masafumi Ohta, Mitsutoshi Anzai, Akihiro Imai
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Patent number: 5595846Abstract: The electrophotgraphic photoreceptor is composed of an electrically conductive substrate having formed thereon a photosensitive layer containing a phthalocyanine mixed crystal comprising titanyl phthalocyanine and hydrogen phthalocyanine, wherein the phthalocyanine mixed crystal has peaks at 6.8.degree., 7.4.degree., 15.0.degree., 24.7.degree., 26.2.degree., and 27.2.degree. of the Bragg angle (2 .theta..+-.0.2.degree.) in the X-ray diffraction spectrum and having a ratio of the peak intensity at 27.2.degree. to the peak intensity at 6.8.degree. of 1 or more. The electrophotographic photoreceptor can output the output signals as digital signals even when the input light is a digital light or an analog light and thus the electrophotographic photoreceptor can be used for an electrophotograph of a digital recording system and even when the photorecetor is used as a conventional photoreceptor for PPC (analog light input), high-quality images having sharp edges can be obtained.Type: GrantFiled: June 20, 1995Date of Patent: January 21, 1997Assignee: Mitsubishi Chemical CorporationInventors: Yasuyuki Shigematsu, Toyoshi Ohashi, Mariko Hayashi, Shinichi Suzuki
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Patent number: 5593805Abstract: A new crystalline form of oxytitanium phthalocyanine is characterized by main peaks specified by Bragg angles (2.theta..+-.0.2 degrees) of 7.4 degrees, 10.2 degrees, 12.5 degrees, 15.0 degrees. 16.3 degrees, 18.3 degrees, 22.4 degrees, 24.2 degrees, 25.2 degrees and 28.5 degrees in X-ray diffraction pattern based on CuK.alpha. characteristic X-rays. The oxytitanium phthalocyanine is formed by treating amorphous oxytitanium phthalocyanine with a solvent selected from the group consisting of monohydric alcohols having at least two carbon atoms, cellosolves, diethylene glycol monoethers and diacetone alcohol. The oxytitanium phthalocyanine is useful as a charge generating material for providing an electrophotographic photosensitive member, which shows a stably high sensitivity to long wavelength light.Type: GrantFiled: April 24, 1992Date of Patent: January 14, 1997Assignee: Canon Kabushiki KaishaInventors: Shintetsu Go, Hideyuki Takai, Hajime Miyazaki, Itaru Yamazaki, Tetsuro Kanemaru, Kazushi Iuchi
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Patent number: 5591555Abstract: An electrophotographic photoconductor, includes metal-free phthalocyanine as a charge-generating substance, wherein the X-ray diffraction spectrum of said metal-free phthalocyanine as measured using CuK.alpha. as a radiation source includes intense diffraction peaks at Bragg angles (2.theta..+-.0.2.degree.) of 7.5.degree., 9.0.degree., 16.6.degree., 17.2.degree., 21.5.degree., 22.2.degree., 23.8.degree., and 28.5.degree., and wherein the infrared absorption spectrum of said metal-free phthalocyanine includes four absorption bands with the maximum absorption intensity at a wavenumber of 716 cm.sup.-1 between a wavenumber of 700 cm.sup.-1 and a wavenumber of 760 cm.sup.-1 and a characteristic absorption band at a wavenumber of 3,291.+-.2 cm.sup.-1.Type: GrantFiled: January 10, 1995Date of Patent: January 7, 1997Assignee: Fuji Electric Co., Ltd.Inventors: Shinichi Tamura, Seishi Terasaki, Tadashi Mimura, Teruaki Kobayashi, Youichi Tei
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Patent number: 5589309Abstract: Disclosed is an electrophotographic photoreceptor comprising a conductive support and provided thereon an intermediate layer, a carrier generation layer containing a carrier generation material and a carrier transportation layer containing a carrier transportation material, wherein said carrier generation layer contains a first perylene compound represented by Formula A and a second perylene compound represented by Formula B as said carrier generation material: ##STR1## wherein Z represents a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent heterocyclic group; and R represents an alkyl group, an aralkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an aromatic hydrocarbon group or a heterocyclic group; ##STR2##Type: GrantFiled: July 17, 1995Date of Patent: December 31, 1996Assignee: Konica CorporationInventors: Tomoko Suzuki, Akira Kinoshita, Hirofumi Hayata, Tomoo Sakimura
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Patent number: 5587262Abstract: A photoconductive imaging member comprised of a supporting substrate, a hydroxygallium phthalocyanine photogenerator layer, a charge transport layer, a photogenerator layer comprised of a mixture of bisbenzimidazo(2,1-a-1',2'-b)anthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline -6,11-dione and bisbenzimidazo(2,1-a:2',1'-a)anthra(2,1,9-def:6,5,10 -d'e'f')diisoquinoline-10, 21-dione, and as a top layer a charge transport layer.Type: GrantFiled: October 2, 1995Date of Patent: December 24, 1996Assignee: Xerox CorporationInventors: Heidi Pinkney, Ah-Mee Hor, Zoran D. Popovic
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Patent number: 5578405Abstract: An electrophotographic photoconductor includes an electroconductive support and a single-layered photoconductive layer formed thereon, containing a charge transporting material, a binder resin, and a simultaneously pulverized mixture including at least one disazo pigment of formula (1) and at least one trisazo pigment of formula (2), which is obtained by simultaneously pulverizing those azo pigments: ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen, a halogen atom, trifluoromethyl group, nitro group or cyano group; R.sup.3 is hydrogen, chlorine, fluorine, iodine, bromine, nitro group or cyano group; and Ar.sup.1, Ar.sup.2 and Ar.sup.3 each is a coupler radical, which may be the same or different.Type: GrantFiled: October 14, 1994Date of Patent: November 26, 1996Assignee: Ricoh CompanyInventors: Takaaki Ikegami, Eiji Kurimoto, Takashi Rokutanzono, Katsuichi Ohta, Masaomi Sasaki, Yasuo Suzuki, Kaoru Tadokoro, Megumi Kawahara, Masayuki Koyano
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Patent number: 5576131Abstract: An electrophotographic photosensitive member is constituted by disposing a photosensitive layer on a support. The photosensitive layer contains oxytitanium phthalocyanine and a specific disazo pigment of the formula (I) or (II) each characterized by having particular coupler residues. The photosensitive layer may preferably include a charge generation layer and a charge transport layer. The charge generation layer may preferably include a first charge generation layer containing the above disazo pigment of the formula (I) or (II) and a second charge generation layer containing the above oxytitanium phthalocyanine. The electrophotographic photosensitive member including the photosensitive layer described above is usable for providing an apparatus unit and an electrophotographic apparatus showing excellent electrophotographic characteristics such as high photosensitivity, good potential stability in repetitive use and good image-forming properties substantially providing no black spots.Type: GrantFiled: November 29, 1994Date of Patent: November 19, 1996Assignee: Canon Kabushiki KaishaInventors: Hideyuki Takai, Koichi Suzuki, Satomi Sugiyama, Mitsuhiro Kunieda
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Patent number: 5569749Abstract: An organic photoconductive material is represented by the following general formula [1]:A.sub.1 --N.dbd.N--B--N.dbd.N--A.sub.2 [1],wherein B is a divalent organic group bonded to nitrogen atoms forming azo groups, A.sub.1 and A.sub.2 are groups different from each other, A.sub.1 is represented by the following general formula [A1]: ##STR1## wherein X is an atomic group which is necessary for forming an aromatic hydrocarbon ring or an aromatic hetero-ring by condensation with the benzene ring, Y is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, m is an integer of 1 to 4, R is an aromatic hydrocarbon ring group or an aromatic hetero-ring group and n is 1 or 2, and A.sub.2 is a group represented by one of the following general formulae [A2] and [A3]: ##STR2## wherein a.sub.1 is a group selected from R, --N.dbd.CH--R and ##STR3## R, X, Y, m and n are the same as those in the general formula [A1] and p is 0 or 1.Type: GrantFiled: January 18, 1996Date of Patent: October 29, 1996Assignee: Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hisao Kouno, Shyouichi Takahashi, Kazuhiro Higashide, Nakaji Komiyama, Osamu Suda, Masaru Hasegawa
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Patent number: 5567559Abstract: An ammonia-modified titanyl phthalocyanine for use in preparing charge generating layer of a photoreceptor is disclosed. The ammonia-modified titanyl phthalocyanine is obtained by a process comprising the following steps: (a) reacting titanium tetrachloride with halogen-containing naphthalene to obtain an unmodified titanyl phthalocyanine; (b) dispersing the unmodified titanyl phthalocyanine in an organic solvent; and (c) subjecting the unmodified titanyl phthalocyanine to an ammonia-induced complexation-mediated crystal transformation so as to obtain the ammonia-modified titanyl phthalocyanine. The ammonia-induced complexation-mediated crystal transformation step can be achieved by either bubbling ammonia gas through the titanyl phthalocyanine-containing organic solution or by adding an ammonia-saturated aqueous solution to the titanyl phthalocyanine-containing organic solution. The ammonia-modified titanyl phthalocyanine is characterized by having Bragg diffraction angles of 7.5, 9.3, 13.6, 14.3, 17.9, 24.Type: GrantFiled: April 11, 1995Date of Patent: October 22, 1996Assignees: Sinonar Corp., Industrial Technology Research InstituteInventors: Chen-Jen Yang, Tsong-Shin Jean, Lung-Tarn Wu, Ching-Liang Yang, Kuei-Fei Teng
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Patent number: 5567558Abstract: A process for the preparation of hydroxygallium phthalocyanines Type A, Type B, Type C, or Type D, which comprises contacting Type V hydroxygallium phthalocyanine with an alcohol.Type: GrantFiled: March 30, 1995Date of Patent: October 22, 1996Assignee: Xerox CorporationInventors: Cheng-Kuo Hsiao, Ah-Mee Hor, Sandra J. Gardner, Roger E. Gaynor, Jacques Poitras
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Patent number: 5536611Abstract: A phthalocyanine pigment dispersion using a dispersing polymer having pendant quaternary ammonium salt groups to form a highly dispersed and stable millbase is described. The pigment dispersion is compatible with poly(vinylbutyral) resins and stable in ketone solvents. The pigment dispersion is particularly useful as a charge-generating or charge-transport material in an organic photoconductor construction.Type: GrantFiled: March 31, 1995Date of Patent: July 16, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ravindra L. Arudi, John C. Haidos
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Patent number: 5534376Abstract: A photoconductive imaging member comprised of a supporting substrate, a photogenerating layer, and a charge transport layer, and wherein said photogenerating layer is comprised of a tetrafluoro hydroxygallium phthalocyanine.Type: GrantFiled: August 3, 1995Date of Patent: July 9, 1996Assignee: Xerox CorporationInventors: James D. Mayo, James M. Duff, Gordon K. Hamer, Sandra J. Gardner
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Patent number: 5529870Abstract: An electrophotographic imaging member is characterized by a halogenindium phthalocyanine produced by dry milling and treating with an organic amine solvent.Type: GrantFiled: May 11, 1995Date of Patent: June 25, 1996Assignee: Xerox CorporationInventors: Steven J. Grammatica, Ah-Mee Hor, Roger E. Gaynor, Alan B. Mistrater, Peter J. Valianatos, John S. Chambers, Rachael A. Forgit, Jacques Poitras
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Patent number: 5529868Abstract: An electrophotographic photoreceptor comprising a conductive substrate having provided thereon a photosensitive layer, wherein said photosensitive layer contains, as charge transporting material (i) at least one triarylamine compound represented by formula (I) ##STR1## wherein the definition of Ar.sub.1, Ar.sub.2 are described in the present specification; and (ii) at least one benzidine compound represented by formula (II) ##STR2## wherein the definition of R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ', R.sub.3, R.sub.3 ', m and n is described in the specification. The photoreceptor maintains its electrical characteristics stably on repeated use.Type: GrantFiled: March 13, 1995Date of Patent: June 25, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Kiyokazu Mashimo, Fumio Ojima, Tomozumi Uesaka, Toru Ishii, Kazuyuki Nakamura, Takahiro Suzuki
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Patent number: 5529869Abstract: An organic positive-charging photoconductor (+) OPC is disclosed. The (+) OPC has a conductive substrate; a hydroxy-containing binder component forming a layer greater than or equal to about 1 micron thick on said substrate; an X-type, metal-free phthalocyanine pigment component uniformly distributed throughout said binder component; and a reactive additive component selected from the list of cross-linkable resins, carboxlyic acid anhydrides, aldehydes, poly-ols, alkoxy silane coupling agents, reactive allyl polymers and dismaleimides, the reactive additive component also being uniformly distributed throughout, and being in cross-linked relation with, the hydroxy-containing binder component with an electron withdrawing functional group and an electron donating functional group in the same molecule. The (+) OPC, which may also contain a co-additive component, exhibits increased stability in a laser printing process.Type: GrantFiled: September 7, 1994Date of Patent: June 25, 1996Assignee: Hewlett-Packard CompanyInventor: Khe C. Nguyen
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Patent number: 5527653Abstract: An electrophotographic photosensitive member includes a conductive substrate and a photosensitive layer thereon. The photosensitive layer contains a disazo pigment having a 1,2-benzofluorenone as a central structure. A process cartridge and an electrophotographic apparatus containing the electrophotographic photosensitive member is also provided.Type: GrantFiled: September 29, 1994Date of Patent: June 18, 1996Assignee: Canon Kabushiki KaishaInventor: Masato Tanaka
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Patent number: 5523189Abstract: An electrophotographic element and a preparation method. The element has a charge generation layer including binder and, dispersed in the binder, a physical mixture of: a high speed titanyl fluorophthalocyanine and a low speed titanyl fluorophthalocyanine. The high speed titanyl fluorophthalocyanine has a first intensity peak with respect to X-rays characteristic of Cu K.alpha. at a wavelength of 1.541 .ANG. of the Bragg angle 2.theta. at 27.degree..+-.0.2.degree. and a second intensity peak at 7.3.degree..+-.0.2.degree.. The second peak has an intensity relative to the first peak of less than 60 percent. The low speed titanyl fluorophthalocyanine has a first intensity peak with respect to X-rays characteristic of Cu K.alpha. at a wavelength of 1.541 .ANG. of the Bragg angle 2.theta. at 6.7.degree..+-.0.2.degree. and a second intensity peak at 23.7.degree..+-.0.2. The second peak has an intensity relative to the first peak of less than 50 percent.Type: GrantFiled: October 27, 1994Date of Patent: June 4, 1996Assignee: Eastman Kodak CompanyInventor: Michel F. Molaire
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Patent number: 5518846Abstract: A novel electrophotographic photoreceptor is provided, comprising on an electrically conductive support a light-sensitive layer containing at least one acetylene disazo compound represented by the general formula (I):Cp--N.dbd.N--Ar.sup.1 --C.tbd.C--Ar.sup.2 N.dbd.N--Cp (I)wherein Ar.sup.1 and Ar.sup.2 each represents an unsubstituted or substituted arylene group, divalent condensed polycyclic aromatic group or divalent aromatic heterocyclic group, with the proviso that Ar.sup.1 and Ar.sup.2 are not phenylene groups at the same time; and Cp represents a coupler residue.Type: GrantFiled: May 1, 1991Date of Patent: May 21, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Satoshi Hoshi, Naonori Makino, Katsuji Kitatani
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Patent number: 5516609Abstract: A methoxy gallium phthalocyanine compound represented by formula (I): ##STR1## wherein X represents a chlorine atom, a bromine atom, or an iodine atom; and n represents an integer of from 0 to 4; and an electrophotographic photoreceptor using the methoxy gallium phthalocyanine compound.Type: GrantFiled: March 30, 1994Date of Patent: May 14, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Daimon, Ryosaku Igarashi
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Patent number: 5512674Abstract: A process for preparing a titanyl phthalocyanine crystal showing at least one diffraction peak at a Bragg angle (2.theta..+-.0.2) of 27.3.degree. is disclosed, which comprises dissolving or suspending titanyl phthalocyanine in concentrated sulfuric acid to form a solution or a slurry and diluting the solution or slurry with an alcohol solvent, an aromatic solvent, a mixed solvent of an alcohol solvent and water, a mixed solvent of an aromatic solvent and water, or a mixed solvent of an alcohol solvent and an aromatic solvent with or without water thereby to precipitate a crystal, and, if desired, treating the precipitated crystal with an alcohol solvent, an aromatic solvent, a mixed solvent of an alcohol solvent and an aromatic solvent or a mixed solvent of an alcohol solvent and/or an aromatic solvent and water. The resulting titanyl phthalocyanine crystal exhibits high photosensitivity and excellent durability as a photoconductive material of an electrophotographic photoreceptor.Type: GrantFiled: December 6, 1993Date of Patent: April 30, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Hidemi Nukada, Akihiko Tokida, Yasuo Sakaguchi, Katsumi Daimon, Katsumi Nukada
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Patent number: 5512400Abstract: There are provided a hydrazone compound represented by formula (I), an electrophotographic photoreceptor which has a photosensitive layer containing the compound on an electrically conductive support, and an organic electroluminescent element containing the compound as a charge transporting material: ##STR1## wherein Ar.sub.1 represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted anthrylene group, Ar.sub.2 represents a substituted or unsubstituted aryl group, R.sub.1 and R.sub.2 each independently represents a hydrogen atom, a halogen atom, an unsubstituted alkyl group, or an unsubstituted alkoxy group, R.sub.3 represents an unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, Z represents an ethylene group or a vinylene group, and n is 0 or 1.Type: GrantFiled: December 15, 1994Date of Patent: April 30, 1996Assignee: Hodogaya Chemical Co., Ltd.Inventors: Atsushi Takesue, Yasuo Murakami, Takanobu Watanabe, Mitsutoshi Anzai
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Patent number: 5510217Abstract: Gallium phthalocyanine halide crystals wherein a part of the crystals are changed into hydroxygallium phthalocyanine is disclosed. A method for preparing gallium phthalocyanine halide crystals wherein gallium phthalocyanine halide crystals are brought into contact with water and a part of the crystals are changed into hydroxygallium phthalocyanine is also disclosed. An electrophotographic photoreceptor formed by laminating at least a charge generating layer and a charge transporting layer successively on a conductive support wherein the charge generating layer contains gallium phthalocyanine halide crystals An which a part of the crystals are changed into hydroxygallium phthalocyanine is also disclosed.Type: GrantFiled: September 30, 1994Date of Patent: April 23, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Kazuya Hongo, Katsumi Nukada, Masakazu Iijima, Noriyoshi Takahashi, Masaaki Suwabe, Hitoshi Takimoto
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Patent number: 5508137Abstract: Certain perylene-3,4:9,10-tetracarboxylic monoanhydride monoimides are condensed with primary diamines or with imidazoles. The products obtained are amidine imides of the formula I ##STR1## where, for example, R.sub.1 is 1-hexylheptyl, R.sub.2 to R.sub.5 are each H and A is 1,2-phenylene. Compounds of the formula I are very light-fast dyes which show strong fluorescence in solution and whose fluorescence occurs at a longer wavelength than that of the bisimides (perylene dyes). The perylene amidine imides of the invention are suitable for example for use as colorants for the mass coloration of macromolecular organic material, as fluorescent dyes or as photoconductors.Type: GrantFiled: August 8, 1994Date of Patent: April 16, 1996Assignee: Ciba-Geigy CorporationInventor: Heinz Langhals
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Patent number: 5501930Abstract: An electrophotographic photoreceptor is herein disclosed which comprises a conductive support and a photosensitive layer formed on the conductive support, and the photosensitive layer contains an enamine derivative as a carrier transport material represented by the formula ##STR1## wherein Ar is an aryl group which may have a substituent, a heterocyclic group which may have a substituent, an aralkyl group which may have a substituent, or a heterocyclic substituted alkyl group; and n is 2, 3 or 4.The electrophotographic photoreceptor is excellent in sensitivity and durability.Type: GrantFiled: August 10, 1994Date of Patent: March 26, 1996Assignee: Sharp Kabushiki KaishaInventors: Akihiro Kondo, Kiyofumi Morimoto, Kazuhiro Emoto
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Patent number: 5501927Abstract: An electrophotographic photoreceptor including a light-sensitive layer containing a bisazo or trisazo compound represented by formula (I-1), (II-1), (III,1), (IV-1), (V-1) or (VI-1): ##STR1##Type: GrantFiled: June 23, 1993Date of Patent: March 26, 1996Assignee: Fuji Xerox Co., Ltd.Inventors: Akira Imai, Toru Ishii, Akihiko Tokida, Yutaka Akasaki
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Patent number: 5498502Abstract: The present invention provides an electrographic printing photosensitive resin composition, which exhibits a good photosensitivity in a negative corona charging system and is useful for a laser platemaking system using semi-conductor laser light within a near infrared range as a light source.Disclosed is a negative charging type printing photosensitive resin composition comprising a phthalocyanine compound (a), a mercaptoarylimidazole (thiazole) compound (b) and, if necessary, a compound selected from the group consisting of a condensed polycyclic quinone compound, a bisazo compound, a cyanine compound, a quinacridone compound and a mixture thereof (d), said compounds being dispersed in a binder resin (c). A printing photosensitive resin plate using the photosensitive resin composition is also disclosed.Type: GrantFiled: January 13, 1995Date of Patent: March 12, 1996Assignee: Nippon Paint Co., Ltd.Inventors: Hisaichi Muramoto, Kazunori Kanda, Yutaka Kanoi
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Patent number: 5496672Abstract: Disclosed are a coating solution for forming a charge generation layer, which comprises:(A) a phthalocyanine composition,(B) a binder resin represented by the formula: ##STR1## wherein R represents an alkylene group, R.sup.1 represents an alkyl group; and m, n and k each represent a ratio of recurring unit numbers and are numerals satisfying the relations of k+m+n=1, n>m>0 and 0.3.gtoreq.k.gtoreq.0,(C) at least one of a melamine resin and a benzoguanamine resin in a 1- to 5-fold amount in terms of the weight ratio of the amount of the binder resin, and(D) a solvent having both a hydroxyl group and an ether group in one molecule,and an electrophotographic photoreceptor using the same.Type: GrantFiled: May 10, 1994Date of Patent: March 5, 1996Assignee: Hitachi Chemical Co., Ltd.Inventors: Takayuki Akimoto, Shigeru Hayashida, Megumi Matsui, Mikio Itagaki
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Patent number: 5494767Abstract: Disclosed are a phthalocyanine composition which comprises having main diffraction peaks at 7.5.degree., 22.5.degree., 24.3.degree., 25.3.degree. and 28.6.degree. of Bragg angles (2.theta..+-.0.2.degree.) in an X-ray diffraction spectrum with Cu K.alpha., a process for preparing the same, an electrophotographic photoreceptor using the same and a coating solution for a charge generation layer containing the same.Type: GrantFiled: January 25, 1994Date of Patent: February 27, 1996Assignee: Hitachi Chemical Company Co., Ltd.Inventors: Mikio Itagaki, Shigeru Hayashida, Megumi Matsui, Hiroko Ishikawa, Yoshii Morishita, Takayuki Akimoto
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Patent number: 5486442Abstract: An alternating copolymer comprising a repeating unit of the formula:-Z-(X-Y).sub.n - (I)wherein n is at least 2, X is O, S, Se or Te, and Y and Z are independently an aromatic or substituted aromatic group, and at least one other repeating unit, which is useful as a photosensitive material used in a spatial light modulator.Type: GrantFiled: July 13, 1993Date of Patent: January 23, 1996Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Akio Takimoto, Hirofumi Wakemoto, Eiichiro Tanaka, Masanori Watanabe, Junko Asayama, Hisahito Ogawa, Shigehiro Sato, Fumiko Yokotani
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Patent number: 5484673Abstract: An electrophotographic photosensitive member of the present invention has a photosensitive lazer containing a compound represented by the formula (1): ##STR1## The electrophotographic photosensitive member has a high sensitivity and can maintain stable and excellent electrophotographic characteristics even when repeatedly used.Type: GrantFiled: February 23, 1995Date of Patent: January 16, 1996Assignee: Canon Kabushiki KaishaInventors: Toshihiro Kikuchi, Akio Maruyama, Noriko Ohtani, Shin Nagahara, Hisami Tanaka, Teigo Sakakibara, Takakazu Tanaka
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Patent number: 5484674Abstract: A process which comprises contacting the cis and trans isomers of benzimidazole perylene with cyclohexane.Type: GrantFiled: October 31, 1994Date of Patent: January 16, 1996Assignee: Xerox CorporationInventors: Ah-Mee Hor, Charles G. Allen, Paul J. Gerroir
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Patent number: 5472816Abstract: A halogen-containing hydroxygallium phthalocyanine crystal showing intense diffraction peaks at Bragg angles (2.theta..degree..+-.0.2.degree.) of (1) 7.7.degree., 16.5.degree., 25.1.degree. and 26.6.degree.; (2) 7.9.degree., 16.5.degree., 24.4.degree., and 27.6.degree.; (3) 7.0.degree., 7.5.degree., 10.5.degree., 11.7.degree., 12.7.degree., 17.3.degree., 18.1.degree., 24.5.degree., 26.2.degree., and 27.1.degree.; 4) 7.5.degree., 9.9.degree., 12.5.degree., 16.3.degree., 18.6.degree., 25.1.degree., and 28.3.degree.; or (5) 6.8.degree., 12.8.degree., 15.8.degree., and 26.0.degree. and an electrophotographic photoreceptor containing the halogen-containing hydroxygallium phthalocyanine crystal as a charge generating material are disclosed.Type: GrantFiled: October 14, 1994Date of Patent: December 5, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Nukada, Katsumi Daimon
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Patent number: 5460909Abstract: A pyrazine compound of formula (I) and a pyrazine compound of formula (II): ##STR1## wherein R is an unsubstituted or substituted phenyl group, an unsubstituted or substituted naphthyl group; and an electrophotographic photoconductor which includes an electroconductive support and a photoconductive layer formed thereon containing a charge generating material and a charge transporting material which is any of the above-mentioned pyrazine compounds of formula (I) and formula (II).Type: GrantFiled: June 15, 1994Date of Patent: October 24, 1995Assignee: Ricoh Company, Ltd.Inventors: Masayuki Shoshi, Yumi Ichikawa, Kaoru Teramura, Masayuki Koyano, Megumi Kawahara
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Patent number: 5459004Abstract: A process for preparing hydroxygallium phthalocyanine crystals showing intense diffraction peaks at Bragg angles (2.theta..+-.0.2) of 7.5.degree., 25.1.degree., and 28.3.degree. with respect to CuK.sub..alpha. characteristic X-rays which comprises mechanically grinding hydroxygallium phthalocyanine and then treating the grains with a solvent is disclosed. The hydroxygallium phthalocyanine crystals obtained by the process of the present invention has a novel crystal form and exhibits high sensitivity and excellent durability on repeated use as well as crystal form stability. The electrophotographic photoreceptor prepared by using the resulting hydroxygallium phthalocyanine exhibits excellent electrophotographic characteristics.Type: GrantFiled: March 29, 1993Date of Patent: October 17, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Katsumi Daimon, Katsumi Nukada, Akira Imai, Masakazu Iijima, Toru Ishii
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Patent number: 5456998Abstract: Photoconductive imaging members comprised of an alkoxy-bridged metallophthalocyanine dimer as a charge generator material, wherein said dimer is of the formula C.sub.32 H.sub.16 N.sub.8 MOROMN.sub.8 H.sub.16 C.sub.Type: GrantFiled: April 26, 1994Date of Patent: October 10, 1995Assignee: Xerox CorporationInventors: Richard A. Burt, Barkev Keoshkerian, George Liebermann, Cheng-Kuo Hsiao, Sandra J. Gardner, Dasarao K. Murti, Katsumi Daimon, Yasuo Sakaguchi, Ryosaku Igarashi
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Patent number: 5449581Abstract: Disclosed are a phthalocyanine composition which comprises having main diffraction peaks at 7.5.degree., 24.2.degree. and 27.3.degree. of Bragg angles (2.theta..+-.0.2.degree.) in an X-ray diffraction spectrum with Cu K.alpha., a process for preparing the same, an electrophotographic photoreceptor using the same and a coating solution for forming a charge generation layer containing the same.Type: GrantFiled: December 28, 1993Date of Patent: September 12, 1995Assignee: Hitachi Chemical Co., Ltd.Inventors: Megumi Matsui, Shigeru Hayashida, Takayuki Akimoto, Mikio Itagaki
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Patent number: 5445909Abstract: An electrophotographic photoreceptor high in sensitivity and contrast potential after light irradiation is disclosed. The photoreceptor comprises an electroconductive substrate having thereon a photoconductive layer comprising a charge generating layer comprising a charge generating material, and a charge transporting layer comprising a charge transporting material, wherein the ionization potential IPg of the charge generating material is lower than the ionization potential IPt of the charge transporting material, the difference therebetween is 0.35 eV or less, and the difference between the ionization potential IPg1 of the charge generating layer and the ionization potential IPt1 of the charge transporting layer is within the range of -0.1 to +0.1 eV.Type: GrantFiled: July 9, 1993Date of Patent: August 29, 1995Assignee: Fuji Xerox Co., Ltd.Inventors: Yutaka Akasaki, Katsuhiro Sato, Katsumi Nukada
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Patent number: 5443935Abstract: An electrophotographic photoreceptor comprising a conductive substrate having thereon a photosensitive layer comprising a binder resin having dispersed therein a phthalocyanine composition is disclosed, in which said binder resin is a curing fluorine resin, and said phthalocyanine composition comprises (A) an unsubstituted phthalocyanine compound and (B) a phthalocyanine derivative having a halogen atom(s) and/or electron attractive group(s) at the benzene nuclei, such that the ratio of the number of the halogen atom(s) and/or electron attractive group(s) to the total number of the phthalocyanine units in (A) and (B) is from 0.001 to 0.5. The photoreceptor has a low threshold value of photosensitive characteristics and exhibits high sensitivity in a digital behavior. Besides applicable to a digital recording system, the photoreceptor, when applied to a conventional PPC system, provides a sharp-edged high quality image.Type: GrantFiled: April 30, 1993Date of Patent: August 22, 1995Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Takashi Kojima, Shinichi Suzuki, Yasuyuki Shigematsu
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Patent number: 5441837Abstract: An imaging member comprised of an optional supporting substrate, a photogenerator layer, and a charge transport layer, and wherein the photogenerator layer is comprised of acetoxymetal phthalocyanine pigments as essentially represented by the formula ##STR1## where R is acetyl, haloacetyl, or mixtures thereof; R' is alkyl, alkoxy, cyano, halogen, or mixtures thereof; M is a metal selected from the group consisting of aluminum, gallium, silicon, germanium and indium; x is 1 or 2; and y is 0, 1 or 2.Type: GrantFiled: July 29, 1994Date of Patent: August 15, 1995Assignee: Xerox CorporationInventors: Beng S. Ong, Cheng-Kuo Hsiao
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Patent number: 5434027Abstract: The present invention is directed to a photoreceptor having an electroconductive support, a barrier layer, a charge generation layer and a charge transport layer, all formed on the support in this order, wherein the barrier layer consists of an alcohol-soluble copolymerized polyamide resin, the charge generation layer contains a compound represented by formula I or II, and the charge transport layer contains a polycarbonate resin having a molecular weight of not less than 100,000, ##STR1## wherein Z represents a groups of atoms necessary to form a substituted or unsubstituted divalent aromatic ring.Type: GrantFiled: December 21, 1993Date of Patent: July 18, 1995Assignee: Konica CorporationInventors: Takeo Oshiba, Yoshihiko Etoh, Asao Matsushima, Yoshiaki Takei
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Patent number: 5429770Abstract: Low-molecular-weight and polymeric liquid-crystalline 2-substituted benzotriazoles of the formula ##STR1## are used as photoconductors or electrophotographic recording materials or as fluorescent dyes for fluorescent displays.Type: GrantFiled: May 18, 1994Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Friedrich Closs, Karl Siemensmeyer, Dirk Funhoff
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Patent number: 5428152Abstract: Disclosed are naphthalocyanine compounds having siloxy groups bonded to a central metal silicon. The compounds can be used as a charge generating substance of an electrophotographic plate having high sensitivity to the longer wavelength light of about 800 nm without conducting a special treatment. The naphthalocyanine compounds are represented by the formula: ##STR1## wherein L is a group of the formula R.sub.1 R.sub.2 R.sub.3 SiO--, and R.sub.1, R.sub.2 and R.sub.3 are each a same alkyl group having 1-3 carbon atoms.Type: GrantFiled: June 10, 1993Date of Patent: June 27, 1995Assignee: Hitachi Chemical Company, Ltd.Inventors: Shigeru Hayashida, Seiji Tai
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Patent number: 5424158Abstract: A photosensitive material for electrophotography, comprises a support and, provided thereon, an organic photoconductive layer of single-layer structure comprising a binder polymer, an electron acceptor substance particulately dispersed in the binder polymer, and a metal-free phthalocyanine molecularly dispersed in the binder polymer.Type: GrantFiled: July 20, 1992Date of Patent: June 13, 1995Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Mutsuaki Murakami, Atsushi Omote, Sohji Tsuchiya
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Patent number: 5419992Abstract: A process for the preparation of aryl amine polycondensation polymers useful in electrophotographic imaging members, which process comprises the interfacial polymerization of an aryl amine diol dissolved in an alkaline aqueous phase with a bifunctional acid halide dissolved in an organic solvent, resulting in polymers with high molecular weight and narrow molecular weight distribution (M.sub.w /M.sub.n) of from between about 50,000 to about 350,000, and a M.sub.w /M.sub.n of from about 1 to about 4.Type: GrantFiled: March 24, 1993Date of Patent: May 30, 1995Assignee: Xerox CorporationInventors: Walter Mychajlowskij, George Liebermann, William W. Limburg, John F. Yanus, Dasarao K. Murti
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Photosensitive composition for use in an OPC comprising X-metal free phtholocyamine and a dispersant
Patent number: 5418101Abstract: A composition of matter, useful in the production of organic photoconductor devices, comprising a dispersion of X-form metal-free phthalocyanine in an organic liquid containing an effective amount of a dispersant.Type: GrantFiled: January 5, 1993Date of Patent: May 23, 1995Assignee: Zeneca LimitedInventors: Marie Holmes, Geoffrey R. Rothwell -
Patent number: H1474Abstract: A process for increasing the imaging cyclic stability of titanyl phthalocyanines by adding to said titanyl phthalocyanines a perylene.Type: GrantFiled: August 13, 1993Date of Patent: August 1, 1995Inventors: Trevor I. Martin, Sharon E. Normandin, Kathleen M. Carmichael, Donald P. Sullivan