Cyanine Dye Patents (Class 430/93)
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Patent number: 7943320Abstract: The present invention relates to novel unsymmetrical cyanine dyes and to methods of performing nucleic acid analysis in the presence of such dyes. More specifically, the present invention relates to novel unsymmetrical cyanine dyes that have high affinity to double-stranded nucleic acids and that do not inhibit amplification reactions, particularly the polymerase chain reaction (PCR).Type: GrantFiled: December 30, 2008Date of Patent: May 17, 2011Assignee: Canon U.S. Life Sciences, Inc.Inventor: Weidong Cao
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Patent number: 7566544Abstract: A process and a kit are provided for detecting differences in two or more samples of protein, including proteins bearing post-translational modifications and peptides. Proteins are prepared, for example, from each of a different group of cell samples or body fluid samples to be compared. Each protein extract is labeled with a different one of a luminescent dye from a matched set of dyes. The matched dyes have generally the same ionic and pH characteristics but emit light at different wavelengths to exhibit a different color upon luminescence detection. The labeled protein extracts are mixed together and separated together by electrophoresis or a chromatographic method. The separation is observed to detect proteins unique to one sample or present in a greater ratio in one sample than in the other. Those unique or excess proteins will fluoresce the color of one of the dyes used. Proteins common to each sample migrate together and fluoresce the same.Type: GrantFiled: May 1, 2002Date of Patent: July 28, 2009Assignee: Carnegie Mellon UniversityInventors: Jonathan Minden, Alan Waggoner, Susan Janet Fowler
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Patent number: 7175953Abstract: The description herein includes cyanine dyes and analogs of the vaso-active intestinal peptide. These are useful to provide peptide-dye conjugates for use as contrast media in optical diagnoses.Type: GrantFiled: July 25, 2003Date of Patent: February 13, 2007Assignee: Institute Fuer Diagnostik ForschungInventors: Kai Licha, Andreas Becker, Wolfhard Semmler, Bertram Wiedenmann, Carsten Hessenius, Rudolf Volkmer-Engert, Jens Schneider-Mergner
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Patent number: 6531282Abstract: The present invention provides a means to identify the alleles present in a DNA-containing sample by providing subsets of loci for amplification by multiplex PCR. The loci include the thirteen CODIS short tandem repeat (STR) loci and amelogenin. The loci within each subset are grouped so that, upon PCR amplification, the amplicons produced within a given subset do not overlap. Differential labeling of subsets makes it possible to further group the subsets into compound multiplexes for co-amplification in a single reaction vessel, and analysis in a single electrophoretic channel.Type: GrantFiled: May 30, 2000Date of Patent: March 11, 2003Assignee: Oligotrail, LLCInventors: Peter C. Dau, Debang Liu
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Patent number: 6399278Abstract: Clean running printing plates for flexographic printing may be prepared by the co-photopolymerization of a mixture comprising a liquid, acrylate or methacrylate-terminated polyurethane oligomer, an ethylenically unsaturated compound, and a photopolymerization initiator. The liquid oligomer is preferably the acrylated or methacrylated reaction product of a diisocyanate, a liquid hydrophobic polyalkylene oxide, and a diol that is at least one of polypropylene oxide and a copolymer of ethylene oxide and propylene oxide, where reaction with a hydroxy-containing acrylate or methacrylate compound incorporates terminal acrylate or methacrylate groups into the oligomer. The photopolymerizable blend may be used to form printing plates for flexographic printing, where the plates have a reduced tendency to pick up paper fibers, dust and dried ink during the printing process. Methodology for preparing the printing plates, and printing with the printing plates of the invention is also provided.Type: GrantFiled: June 10, 1996Date of Patent: June 4, 2002Inventor: Douglas R. Leach
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Patent number: 6342326Abstract: This invention provides dyes, particularly cyanine and related dyes, with acyl fluoride activating groups, the dyes having the general formula wherein: each dotted line represents carbon atoms necessary to form a fused substituted or unsubstituted aromatic ring; n is an integer selected from the group consisting of 1, 2 and 3; X and Y are selected from the group consisting of S, O, N, CH2 and C(CH3)2; at least one of said R1 and R2 comprises a sulfonic acid or sulfonate group attached to the aromatic ring; and R3 and R4 are independently selected from the group consisting of alkylcarboxylate, activated alkylcarboxylate and an inert group; wherein at least one of said R3 and R4 groups is alcylcarboxylate or activated alkylcarboxylate with the carboxyl group converted to an acyl fluoride. The inert group is a group that is inert towards acyl fluoride and has a sterical structure which allows aminoacylation of the acyl fluoride group.Type: GrantFiled: May 10, 2000Date of Patent: January 29, 2002Assignee: Beckman Coulter, Inc.Inventor: Raymond C. Milton
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Patent number: 6110630Abstract: Activating groups based on N-hydroxynaphthalimide, are disclosed herein. The activating groups can mediate the coupling of labeling moieties, such as biotin or cyanine dyes, to a variety of components, including chain terminators, nucleoside triphosphates, and oligonucleotides, which are used in nucleotide sequencing. From these activating groups, activated esters of the labeling moieties can be prepared. The activated esters react with a component, for example a derivatized nucleotide chain terminator, to give a labeled component. In additions, methods of the present invention provide for labeling a nucleoside triphosphate in organic media. The activating groups and methods of the present invention allow the activation and coupling reactions to occur at a much higher yield, compared with the prior art.Type: GrantFiled: June 18, 1998Date of Patent: August 29, 2000Assignee: Beckman Coulter, Inc.Inventors: M. Parameswara Reddy, Maged A. Michael, Firdous Farooqui, Naeem B. Hanna
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Patent number: 5700647Abstract: To provide a reagent with excellent stability under storage, which can detect a subject compound to be measured with higher specificity and sensitibity.Type: GrantFiled: December 7, 1995Date of Patent: December 23, 1997Assignee: Canon Kabushiki KaishaInventors: Takeshi Miyazaki, Kazumi Tanaka, Tsuyoshi Santo, Toshikazu Ohnishi, Tetsuro Fukui, Tadashi Okamoto
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Patent number: 5639849Abstract: Novel fumaronitriles and dicyanophenanthrenes, for example, bis(4-fluorophenyl)fumaronitrile and 3,6-difluoro-9,10-dicyanophenanthrene which can be produced from the fumaronitrile, produce useful homopolymers and copolymers for high temperature applications; the homopolymers and copolymers derived from the dicyanophenanthrenes can be converted to colored phthalocyanine group-containing polymers which are soluble in organic solvents and can be cast as films which may form the charge generating layer of an electrophotography device.Type: GrantFiled: March 1, 1996Date of Patent: June 17, 1997Inventor: Allan S. Hay
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Patent number: 5573879Abstract: An electrophotographic light-sensitive material which has improved electrostatic characteristics and image forming performance and is excellent particularly in reproducibility of highly accurate image using a liquid developer and image forming performance upon a scanning exposure system using a laser beam of a low power.The electrophotographic light-sensitive material contains, as a binder resin, at least one resin (A) which has a weight average molecular weight of from 1.times.10.sup.3 to 2.times.10.sup.4 and contains not less than 30% by weight of a polymer component of the formula (I) and from 0.5 to 15% by weight of a specified polar group-containing polymer component and at least one resin (B) which is a starlike polymer having a weight average molecular weight of from 3.times.10.sup.4 to 1.times.10.sup.6 and comprising an organic molecule having bonded thereto at least three polymer chains each containing a polymer component containing a specified polar group and a polymer component of the formula (I).Type: GrantFiled: November 2, 1993Date of Patent: November 12, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Kazuo Ishii
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Patent number: 5460912Abstract: The present invention is to provide an electrophotography type lithographic form plate having a high sensitivity and a superior photosensitive characteristic as a photosensitive material for a semiconductor laser beam as well as having an excellent printability as a lithographic form plate. The form plate comprises an electroconductive support member and a photosensitive layer formed thereon and containing a sensitizer mainly consisting of zinc oxide and a binder resin, wherein the sensitizer is at least one compound selected from a group of dye compounds represented by the following general formula (I), and a total acid value of the binder resin is within a range of 3.0 through 10.0. ##STR1## wherein, in the above formula, n represents 2 or 3; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hyrogen atoms, lower alkyl groups, lower alkoxy groups, or halogen atoms, and X-represents an acid anion.Type: GrantFiled: June 4, 1993Date of Patent: October 24, 1995Assignee: Iwatsu Electric Co., Ltd.Inventors: Hideyuki Yamamoto, Kazumasa Hijikata
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Patent number: 5459005Abstract: An electrophotographic light-sensitive material which is excellent in image reproducibility, moisture resistance and anti-abrasion property, provides clear images of good quality and is particularly useful in a scanning exposure system using a semiconductor laser beam is provided.The electrophotographic light-sensitive material contains, as a binder resin, a resin (A) which has an acid value of from 5 to 120 and contains a component of the formula (I) shown below and a specified polar group-containing component and a resin (B) which is an AB or ABA block copolymer comprising an A block containing a component of the formula (II) shown below and a B block containing a component derived from a specific macromonomer having a specified polar group.In the formulae (I) and (II) below, a.sup.1 and a.sup.2 each represents a hydrogen atom, a halogen atom, a cyano group, a hydrocarbon group, --COOR.sup.4 or --COOR.sup.4 bonded via a hydrocarbon group (R.sup.4 represents a hydrocarbon group); and R.sup.11 and R.sup.Type: GrantFiled: February 3, 1994Date of Patent: October 17, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Kazuo Ishii
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Patent number: 5393625Abstract: Disclosed is electrophotolithographic plate precursor having on a conductive support at least one photoconductive layer containing at least a random copolymer binder resin (P) (i) having a weight average molecular weight of from 5.times.10.sup.4 to 5.times.10.sup.5, (ii) comprising (a) a polymer component comprising particular methacrylate or acrylate monomers, (b) a polymer component containing at least one particular polar group and (c) a polymer component having a Fedors' solution parameter of 9.0 or more and containing at least a particular aprotic polar group, and (iii) having at least a particular polar group at one end of the main chain of the copolymer. The plate precursor may be etched with a combination of an etchant and a wetting water both having no problem in the environmental sanitation, to be formed into an offset printing plate not generating background staining. The printing plate has high printing durability and has excellent rubbing resistance.Type: GrantFiled: January 13, 1994Date of Patent: February 28, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Seishi Kasai, Kazuo Ishii
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Patent number: 5382488Abstract: An electrophotographic light-sensitive material which has improved electrostatic characteristics and image forming performance and is excellent particularly in reproducibility of highly accurate image using a liquid developer and image forming performance upon a scanning exposure system using a laser beam of a low power.The electrophotographic light-sensitive material contains, as a binder resin, a low molecular weight resin (A) comprising an organic molecule having bonded thereto at least three polymer chains each containing a polymer component of formula (I) and a polymer component having a specified polar group, and a resin (B) which is a medium to high molecular weight AB block copolymer comprising an A block containing a specified polar group and a B block containing a polymer component of formula (I). ##STR1## wherein a.sup.1 and a2: hydrogen, halogen, a cyano group, a hydrocarbon group, --COOR.sup.4 or --COOR.sup.4 bonded via a hydrocarbon group (R.sup.4 : hydrocarbon group); and R.sup.Type: GrantFiled: May 18, 1993Date of Patent: January 17, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Kazuo Ishii
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Patent number: 5370956Abstract: The invention provides an electrophotographic photoreceptor which has a practical high sensitivity to red light or infrared ray, especially semiconductor laser beam and is excellent in storage stability. The photoconductor layer of this photoreceptor comprises comprises an inorganic photoconductor, a binder resin, a sensitizing dye and optionally an acid anhydride, wherein said sensitizing dye is at least one of dye compounds represented by the following formulas [I], [II], [III] and [IV]: ##STR1## In the above formulas, the respective symbols are as defined hereinbefore.Type: GrantFiled: December 23, 1992Date of Patent: December 6, 1994Assignee: Mitsubishi Paper Mills LimitedInventors: Hirokazu Yamamoto, Minoru Ohashi, Akira Tanaka, Shoji Tazuki
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Patent number: 5362590Abstract: A laser-sensitive electrophotographic lithograph printing plate material having excellent sensitivity to light having a long wavelength of from 700 to 1000 nm, a high thermal resistance and persistency, and high resistance to a change of sensitivity with time, provided with a laser-sensitive photoconductive layer formed on a substrate and comprising a photoconductive pigment; a sensitizing dye comprising at least one compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are respectively --CH.sub.3, --C.sub.2 H.sub.5, or --CH.sub.2 --CH.dbd.CH.sub.2 and X is a halogen atom, an antioxidant comprising at least one member selected from radical chain terminators, peroxide-decomposing agents, and heavy metal-deactivating agents, and an electrically insulating binder.Type: GrantFiled: August 13, 1992Date of Patent: November 8, 1994Assignee: Oji Paper Co., Ltd.Inventor: Shiro Nakano
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Patent number: 5294507Abstract: An electrophotographic lithographic printing plate precursor having a photoconductive layer containing resin (A) having a weight average molecular weight of from 1.times.10.sup.3 to 2.times.10.sup.4 and containing a polymer component of the specified repeating unit and a polymer component having a polar group and dispersed resin grain (L) which is obtained by dispersion polymerization of monomer (C) containing a functional group capable of forming at least one group selected from a thiol group, a sulfo group, an amino group and a ##STR1## group upon decomposition in the presence of a dispersion stabilizing resin soluble in a non-aqueous solvent and which has a silicon and/or fluorine atom-containing substituent.The electrophotographic lithographic printing plate precursor has good electrophotographic characteristics and water retentivity due to the suitable interaction between zinc oxide, a spectral sensitizing dye, the resin (A) and the dispersed resin grain (L).Type: GrantFiled: December 14, 1992Date of Patent: March 15, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Seishi Kasai
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Patent number: 5213930Abstract: An electrophotographic lithograph printing plate material having an enhanced sensitivity to laser rays, an excellent heat resistance and a low dark decay comprises an electroconductive, water-resistant substrate and an electrophotographic layer comprising a photoconductive zinc oxide, a resinous binder and a sensitizing dye material which comprises at least one compound (A) of the formula (I) and at least one compound (B) of the formula (II): ##STR1## wherein each of A.sub.1 and A.sub.2 represents a C.sub.5-7 polymethine group non-substituted or substituted with at least one substituent, for example, --Cl, the substituted polymethine group may have a cyclic structure, for example, of: ##STR2## each of from B.sub.1 to B.sub.4 is a divalent non-substituted or substituted, benzene or naphthalene group, each of from X.sub.1 to X.sub.4 is a S, Se, or O atom or a --C(CH.sub.3).sub.2 -- group, each of from R.sub.1 to R.sub.4 is a C.sub.1-5 alkyl group, each of M.sub.1 and M.sub.Type: GrantFiled: October 28, 1991Date of Patent: May 25, 1993Assignee: Oji Paper Co., Ltd.Inventors: Masahiro Yamana, Koji Sato
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Patent number: 5200286Abstract: An electrophotographic photoreceptor is disclosed, comprising a substrate having thereon at least an electric charge generating layer and an electric charge transporting layer, characterized in that the electric charge generating layer is formed from a coating solution which is prepared by dispersing an electric charge generating material and an acid in a binder resin solution. Useful acids are inorganic acids, including hydrochloric acid, sulfuric acid, hydrobromic acid and phosphoric acid, and organic acids, including formic acid, acetic acid, propionic acid, butryric acid, lactic acid, benzoic acid and sulfonic acid. This material has an increased sensitivity and thus can be effectively used in copying machines.Type: GrantFiled: February 6, 1991Date of Patent: April 6, 1993Assignee: Fuji Xerox Co., Ltd.Inventors: Yuichi Yashiki, Kazuya Hongo, Seiji Ashiya
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Patent number: 5114817Abstract: Disclosed is a photosensitive toner sensitive to light with wavelengths in the range of 600 to 700 nm, which includes zinc oxide, a sensitizing dye, and a resinous binder. The sensitizing dye is a cyanine dye which is represented by the following general formula (I): ##STR1## R is CH.sub.3, C.sub.2 H.sub.5, n-C.sub.4 H.sub.9, n-C.sub.7 H.sub.15, CH.sub.2 COOH, C.sub.2 H.sub.4 COOH or allyl, and X is I, Cl, Br, NO.sub.3 or tolylsulfonyl.Type: GrantFiled: June 11, 1990Date of Patent: May 19, 1992Assignee: Mita Industrial Co., Ltd.Inventors: Akiyoshi Urano, Yumiko Sano
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Patent number: 4954413Abstract: A method for making a photoconductive powder which comprises the steps of preparing fine particles of metal oxide or metal hydroxide by hydrolyzing a metal alkoxide or metal acetylacetonate; and immersing the fine particles into pigment containing suspensions to provide three types of composite particles. Each of the suspensions contains a respective pigment having a spectral absorption band within the wavelength region of a one of the primary colors of the additive principle. Each type of the resultant composite particles is composed of the fine particles of the metal oxide or metal hydroxide and the associated pigment as a principal component.Type: GrantFiled: October 18, 1989Date of Patent: September 4, 1990Assignee: Mitsubishi Denki Kabushiki KaishaInventors: Fusaoki Uchikawa, Kenji Nomura
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Patent number: 4929527Abstract: A photoconductive composition which exhibits excellent dark reduction retention, excellent sensitivity to radiation from the near infrared region to the infrared region as well as excellent long-term stability, is comprised of an inorganic photoconductor, a cyclic acid anhydride and a spectral sensitizing dye dispersed in a binding resin. A laser beam scanning exposure can be performed on said composition to produce electrophotographic images.Type: GrantFiled: April 22, 1988Date of Patent: May 29, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Shigeru Ohno, Kazuo Ishii, Ryosuke Itakura
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Patent number: 4879195Abstract: An electrophotographic material having an enhanced sensitivity to laser rays comprises,(A) an electroconductive substrate, and(B) a laser-sensitive electrophotographic layer comprising (a) a finely divided photoconductive zinc oxide, (b) a resinous binder, (c) a sensitizing coloring material comprising at least one member selected from the compounds of the formulae (I) and (II): ##STR1## in which m.sup.1, m.sup.2, n.sup.1 and n.sup.2 are 1 to 8, R.sup.1 and R.sup.2 are --COO or --SO.sub.3, R.sup.3 and R.sup.4 are H, --CH.dbd.CH.sub.2 --COOH, --SO.sub.3 H, --COONa, --SO.sub.3 Na, COOK or --SO.sub.3 K, X is Cl, Br, I or --ClO.sub.4, ##STR2## and, (d) a sensitizing assistant comprising at least one carboxylic anhydride of the formula (III): ##STR3## wherein R.sup.5 and R.sup.6 are H, C.sub.1-8 alkyl or phenyl.Type: GrantFiled: December 16, 1988Date of Patent: November 7, 1989Assignee: Oji Paper Co., Ltd.Inventors: Kunitaka Toyofuku, Hiroaki Sato, Kohei Michikawa
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Patent number: 4857431Abstract: A photoconductive composition is disclosed, comprising at least an inorganic photoconductive material, a sensitizing dye and a resin binder wherein the sensitizing dye is a compound containing at least one acidic group in the molecule thereof as represented by the formula (I): ##STR1## wherein all the symbols are as defined in the appended claims.Type: GrantFiled: November 16, 1987Date of Patent: August 15, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Eiichi Kato, Kazuo Ishii
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Patent number: 4853310Abstract: Cyanine dyes, particularly indocyanine dyes, having at least 7 carbon atoms in the polymethine chain which may possess a fused cyclopentene or cyclohexene ring in the form of a tri-iodide salt exhibit a substantial reduction in the propensity to associate compared to dyes having the identical cation but different anion. The tri-iodide salts are particularly useful as sensitizers in organic photoconductor systems.Type: GrantFiled: May 20, 1988Date of Patent: August 1, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: David E. Brown, Louis M. Leichter
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Patent number: 4741983Abstract: A photoconductive composition useful in electrophotography comprising a mixture of photoconductive zinc oxide, a binder, a first dye which absorbs near infrared radiation and which is effective in sensitizing the zinc oxide to near infrared radiation, and a second dye which absorbs visible radiation, sensitizes zinc oxide to such visible radiation and is effective in enhancing the discharge rate of the sensitized zinc oxide at any given intensity of the near infrared radiation is provided. A paper base sheet coated with such a photoconductive composition can be used in the preparation of an electrophotographic image.Type: GrantFiled: January 28, 1987Date of Patent: May 3, 1988Assignee: AM International, Inc.Inventor: Leonard Skuby
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Patent number: 4699862Abstract: An electrophotoconductor comprising a photosensitive layer containing (a) a zinc oxide compound, (b) a phthalocyanine compound, (c) a hole transporting material and (d) a binder resin.Type: GrantFiled: July 1, 1986Date of Patent: October 13, 1987Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Nguyen C. Khe, Masanobu Nakamura, Midori Fukawatase, Kenji Takahashi
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Patent number: 4663261Abstract: An electrophotographic recording material is disclosed which comprises an electrically conductive support and a photoconductive layer containing a photoconductor comprised of zinc oxide, a binder, and a sensitizing agent comprised of an alkylated trimethine-cyanine dye having a particular structure. The disclosed electrophotographic material possesses a sharply pronounced, selective sensitization having a peak at about 495 nm, and can be safely handled under green, yellow and red safelights.Type: GrantFiled: February 13, 1985Date of Patent: May 5, 1987Assignee: Hoechst AktiengesellschaftInventors: Werner Franke, Richard Brahm
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Patent number: 4657836Abstract: In an electrophotographic recording material comprising an electrically conductive base material and at least one photoconductive layer containing a photoconductor, a binder and at least three sensitizing dyes of which at least two are 3,3'-dimethylindolenine compounds, such as bis-(3,3'-dimethylindolenyl)-trimethinecyanines and -pentamethinecyanines, having a sensitizing action in different wavelength regions, it is possible to sensitize various organic and inorganic photoconductors within the range from about 400 to 700 nm.Type: GrantFiled: March 5, 1986Date of Patent: April 14, 1987Assignee: Hoechst AktiengesellschaftInventors: Werner Franke, Richard Brahm
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Thermally-stable, infrared-sensitive zinc oxide electrophotographic compositions element and process
Patent number: 4418135Abstract: Electrophotographic compositions containing zinc oxide dispersed in a certain resin binder mixture and sensitized with a cyanine dye having a particular structure provide high sensitivity in the 780-840 nm wavelength range, excellent thermal stability, long dark decay time and near-white appearance. The compositions are particularly useful for non-transfer electrophotography and for electrostatic printing applications.Type: GrantFiled: September 22, 1982Date of Patent: November 29, 1983Assignee: Allied CorporationInventors: Karl W. Beeson, Himangshu R. Bhattacharjee, Frederick R. Hopf -
Patent number: 4362800Abstract: A photoconductive composition for electrophotography containing a photoconductive material, a sensitizing dye comprising a specific very stable sensitizing dye for red light to infrared rays, and a film-forming polymer binder.Type: GrantFiled: September 4, 1981Date of Patent: December 7, 1982Assignee: Fuji Photo Film Co., Ltd.Inventors: Masaaki Takimoto, Kenichi Sawada, Kouichi Kawamura