Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
  • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/18—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/20—Oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
  • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
  • C07D221/04—Ortho- or peri-condensed ring systems
  • C07D221/06—Ring systems of three rings
  • C07D221/10—Aza-phenanthrenes
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
  • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
  • C07D221/04—Ortho- or peri-condensed ring systems
  • C07D221/18—Ring systems of four or more rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
  • C07D491/04—Ortho-condensed systems
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0622—Heterocyclic compounds
  • G03G5/0624—Heterocyclic compounds containing one hetero ring
  • G03G5/0635—Heterocyclic compounds containing one hetero ring being six-membered
  • G03G5/0637—Heterocyclic compounds containing one hetero ring being six-membered containing one hetero atom
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording-members for original recording by exposure, e.g. to light, to heat or to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0622—Heterocyclic compounds
  • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
  • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring

Definitions

• R represents a (C -C alkyl radical
• Z represents the necessary atoms to close an adjacent ring system of the fluorene series
• an efficient photoconductive particularly photosensitive recording member can be formed by using in its composition a photoconductive compound corresponding to the following general formula:
• R represents hydrogen or an alkyl group, e.g., a
• X represents oxygen or sulphur N 1'1 wherein:
• X represents oxygen or sulphur
• R represents hydrogen or an alkyl group, e.g., a methyl group or ethyl group.
• R represents hydrogen or an alkyl group, e.g., a methyl or ethyl group
• non-ionic substituents are: an alkyl group, e.g., methyl, halogen, e.g., fluorine, chlorine, bromine or iodine, a nitro group, an alkoxy group, e.g., methoxy, an amino group, a substituted amino group, e.g., a monoalkylamino or dialkylamino group or a cyano group.
• ketones examples include acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl butyl ketone.
• reaction mixture was subjected to diminished pressure to remove the volatile products.
• the residue was dissolved in methylene chloride and washed in subsequent order 3 times with 5N aqueous hydrochloric acid 3 times with an aqueous 30 percent sodium hydroxide solution 3 times with water.
• the methylene chloride solution was dried on anhydrous sodium sulphate and the solvent driven off.
• the residue was purified by column chromatography using a column provided with silica gel as adsorbers and as eluent a mixture of methylene chloride/benzene (8:2 by volume). This purification was repeated twice.
• reaction mixture was subjected to diminshed pressure to further remove the volatile products.
• residue was dissolved in methylene chloride and washed in subsequent order:
• the methylene chloride solution was dried on anhydrous sodium sulphate and the solvent driven off.
• the residue was purified by boiling it three times with a small amount of a petroleum fraction boiling between l20C and active carbon.
• reaction product was purified as described for compound 3. Yield: 5 g. Oily product.
• the photoconductive compounds applied according to the present invention may be used alone or in combination with substances imparting desired chemical or physical properties to the recording element. So, these substances can be combined with other substances that either or not are photoconductive and exert an influence, e.g., on the dark-resistivity, the dischargeability or conductivity of the recording layer by an exposure to electromagnetic radiation, or on the transparency or the quality of the final image, e. g., by counteracting the fringe effect as described in the United Kingdom Pat. specification 1,007,349 filed Oct. 12, 1961 by Gevaert Photo-Producten N.V.
• the recording elements according to the present invention preferably contain at least 5 percent by weight of a photoconductive l,2dihydroquinoline derivative being within the scope of the above general formulae.
• the recording element preferably consists for at least 10 percent by weight of one or more of the said 1,2-dihydroquinoline derivatives.
• the electrically insulating binding agent used in a recording layer containing said derivative may provide the desired mechanical strength for instance to form a selfsupporting layer, and preferably has a resistivity of at least 10 ohm.cm.
• the recording layer consists of the photoconductor, which, e.g., has been applied to a suitable support in molten state forming a micro-crystalline or glass-like layer on cooling.
• This technique can be applied when the photoconductive recording element has not to possess a high mechanical strength.
• reference is made to the Canadian Pat. specification 712,541 filed Feb. 5, 1960 by Gevaert Photo-Producten N.V.
• Macromolecular compounds suitable for use as insulating binding agent for the photo-conductive compounds are. e.g., natural resins such as dammar resin, gum arabic, microcrystalline waxes, modified natural substances such as cellulose diacetate, cellulose triacetate, and ethyl cellulose, pentaerythrite polyesters or modified colophony resins and ester gums, polymers such as polyethylene, polystyrene and copolymers of styrene, polyvinyl acetate and copolymers of vinyl acetate, polyvinyl acetals of formaldehyde, acetaldehyde or butyraldehyde, polyacrylic acid esters and polymethacrylic acid esters, coumarine-indene resins epoxy resins and polycondensates such as glycerol-phthalate resins and other glyceryl polyesters, alkyd resins, diethylene glycol polyesters, formaldehyde resins and silicone resm
• a material suitable for use in electrophotography comprises a photoconductive layer incorporating an organic monomeric photoconductor and a halogen-containing polymer in such layer or in a juxtaposed layer (if any), the sensitivity of said photoconductor having been increased by making it to interact with said halogen-containing polymer by heating.
• photoconductive polymers e.g., those containing N-vinyl carbazole recurring units and other known monomeric and polymeric organic photoconductors, e.g., those described in the published Dutch Pat. application 70/04174 filed Mar. 24, 1970 by Gevaert-Agfa NV.
• the inherent spectral sensitivity of most of the photoconductive compounds listed in Tables I and II is mainly situated in the near U.V. range, i.e., in the range of 360 to 420 nm.
• the spectral sensitivity of recording materials according to the present invention can be increased in different ways, e.g., by adding so-called spectral sensitizing agents for the photoconductive substances contained in the recording element or by admixing to the said heterocyclic organic photoconductive compounds other photoconductive substances, the inherent sensitivity of which for a particular part of the electromagnetic radiation spectrum is higher than that of the present compounds.
• semi-transparent recording layers are prepared, in which said heterocyclic photoconductive compounds are used in admixture with (an) inorganic photoconductive substance(s), especially photoconductive substances of the group of zinc oxide, photoconductive lead(ll) oxide and photoconductive cadmium sulphide or cadmium selenide.
• an inorganic photoconductive substance(s) especially photoconductive substances of the group of zinc oxide, photoconductive lead(ll) oxide and photoconductive cadmium sulphide or cadmium selenide.
• Suitable spectral sensitizing dyestuffs for the organic photoconductor are among others organic dyestuffs, known as methine dyes, or xanthene dyes of which the phthaleins and rhodamines are subclasses, and triarylmethane dyes, e.g., crystal violet (C.I. 42,555) and the triarylmethane dyes described in published Dutch Pat. application 6704706 filed Apr. 3, 1967 by Gevaert- Agfa NV.
• methine dyes includes monoas well as polymethine dyes which dyes are known to those skilled in the art of the spectral sensitization of light-sensitive silver halide.
• Preferred methine dyes are of the cationic type.
• Rhodamine B C.I. 45,170
• Rose Bengale C.I. 45,440
• Fluorescein C.I. 45,350
• spectral sensitizing dyes are preferably added to the recording layer composition in a proportion of 0.01 to percent by weight in respect of the photoconductive substance(s).
• methine dyes are within the scope of the following general formulae:
• A stands for a dimethine or tetramethine group including a substituted dimethine or tetramethine group
• n stands for l or 2
• R stands for alkyl including substituted alkyl, an unsaturated aliphatic group, e.g., allyl, aralkyl including substituted aralkyl, aryl including substituted aryl or cycloalkyl,
• R stands for alkyl, aryl including substituted aryl, e.g., phenyl and phenyl substituted preferably in the pposition by alkyl, halogen and alkoxy, a 5- or 6- membered heterocycle the heteroatom of which is oxygen, sulphur, selenium or nitrogen such as 2-, 3-, or 4- pyridyl, 2-furyl, Z-thienyl, etc. including their quaternary salts,
• R stands for hydrogen or has one of the meanings given for R,
• R stands for hydrogen, alkyl, alkoxy or halogen or together with R forms an alkylene bridge such as dimethylene and trimethylene,
• each of R and R stands for hydrogen, alkyl, alkoxy or halogen or together represent the atoms necessary to complete a fused-on benzene nucleus;
• X represents an anion, e.g., Cl, Br, I, C10 CH SOJ, or
• zothiazole series e.g., benzothiazole, 4- chlorobenzothiazole, 5-chlorobenzothiazole, 6- chlorobenzothiazole, 7-chlorobenzothiazole, 4- methylbenzothiazole, S-methylbenzothiazole, 6- methylbenzothiazole, 5-bromobenzothiazole, 6- bromobenzothiazole, 6-sulphobenzothiazole, 4- phenylbenzothiazole, S-phenylbenzothiazole, 4- methoxybenzothiazole, S-methoxybenzothiazole, 6- methoxybenzothiazole, I 5-iodobenzothiazole, 6- iodobenzothiazole 4-ethoxybenzothiazole, 5
• ethoxybenzothiazole 4,5,6,7-tetrahydrobenzothiazole, 5 ,6-dimethoxybenzothiazole, 5 ,6-dioxymethylenebenzothiazole, S-hydroxybenzothiazole, 6- hydroxybenzothiazole, 5,6-dimethylbenzothiazole, those of the naphthothiazole series, e.g., naphtho[2,ld]thiaz0le, naphtho [l,2-d]thiazole, S-methoxynaphtho[ l,2-d]-thiazole, 5-ethoxynaphtho[ 1,2-d]-thiazole, 3-methoxynaphtho[ 2, l -d]-thiazole, 7-methoxynaphtho[2,l-d]-thiazole, those of the thionaphtheno [7,6- d]-thiazole series, e.g.,
• tetrahydrobenzoselenazole those of the naphthoselenazole series, e.g., naphtho[2,l-d]selenazole, naphtho[l,2-d]selenazole, those of the thiazoline series, e.g., thiazoline, 4-mcthylthiaz0line, 4-hydroxymethyl- 4-methylthiazoline, 4,6-bis-hydroxymethylthiazoline, those of the oxazoline series, e.g., oxazoline, those of the selenazoline series, e.g., selenazoline, those of the 2-quinoline series, e.g., quinoline, 3-methylquinoline,
• A stands for a monomethine or trimethine group including a substituted monomethine or trimethine group
• each of R' R and R" RQ (the same or different) has one of the meanings given for R R X; has the same significance as Xf;
• each of R, and R (the same or different) has one of the meanings given for Rn X has the same meaning as X.
• A has the same meaning as A each of m and p (the same or different) stands for l or 2, and
• each of Z, and Z stands for the atoms necessary to complete a heterocyclic nucleus of the thiazole, benzothiazole, naphthothiazole, thionaphtheno[7,6-d]-thiazole, thiadiazole, oxazole, benzoxazole, naphthoxazole, selenazole, benzoselenazole, naphthoselenazole, 2-quinoline, 4-quinoline, pyrimidine, quinoxaline, quinazoline, 2-pyridine, 3,3- dialkylindolenine or of the benzimidazole series; representative examples of these heterocyclic nuclei can be found above in the definition of Z in formula 1.
• the dyestuffs corresponding to the above general formulae can be prepared according to the methods lsnown by those skilled in the art of methine dye chemistry.
• the recording material contains one or more substances that increase the photoconductivity of the recording material in the inherent spectral sensitivity range of the said heterocyclic organic photoconductive compounds.
• a binding agent can act as a sensitizing agent that enhances the total sensitivity of the recording element.
• compounds containing one or more electron-attracting atoms or groups e.g., those that are known as nonionic Lewis acids, e.g., the Lewis acids that can form a charge transfer complex as described in U.S. Pat.
• the l,2-dihydroquinoline derivatives may be used in admixture with diazonium salts that on exposure to electromagnetic radiation produce (a) radical(s) that irreversibly increase(s) the electro-conductivity of a recording layer.
• diazonium salts that on exposure to electromagnetic radiation produce (a) radical(s) that irreversibly increase(s) the electro-conductivity of a recording layer.
• Such substances as well as details about their incorporation into a recording layer containing an organic photoconductive insulating substance are described in the United Kingdom Pat. specification 964,872 filed Apr. 22, 1959 by Gevaert Photo- Producten NV. and the US. Pat. specification 3,113,022 of Paul Maria Cassiers, Jean Marie Nys, Jozef Frans Willems and Rene Maurice l-lart issued Dec. 3, 1963.
• a particularly suitable conductivityincreasing diazonium compound is p-nitrobenzenediazonium chloride.
• the diazonium compounds are preferably used in an
• additives well known in the art of preparing photoconductive coatings for recording purposes may he used, e.g., matting agents, fluorescing compounds, phosphors, optical brightening agents, agents controlling the adhcsive power of the recording layer, agents controlling the elasticity, the plasticity and the hardness of the recording layer, agents controlling the viscosity of the coating composition, antioxidants, glossimproving agents, etc.
• Transparent and semi-transparent recording materials containing the photoconductive heterocyclic organic compounds as described hereinbefore are especially suited for use in recording materials applied for the production and reproduction of microfilm images.
• Microfilm images can be copied in contact or enlarged optically on recording materials according to the present invention.
• the transparencies obtained can serve as negative or positive intermediate prints for further printing, e.g., on diazotype materials.
• the semitransparent recording materials according to the present invention preferably have an optical density not larger than 0.30 towards visible light or the copying light used in the printing apparatus wherein it is used as intermediate print.
• the photoconductive heterocyclic organic compounds described hereinbefore are further especially suited for being applied in the manufacture of pigment images wherein the latter may have the properties of a fluorescent compound or phosphor.
• luminexcent phosphors are used in screens of cathode-ray tubes and more particularly in television, X-ray, radar and oscilloscgpescreens.
• Tn colour television screens phosphors of different colour have to be fixed on a screen in a particular pattern.
• a pattern of a phosphor on a screen support is produced by the steps of applying to said support a coating of an electroconductive material and to said coating a layer comprising a vaporisable or thermolysable photoconductive compound optionally incorporated in a vaporisable or thermolysable binding agent.
• an electrostatic charge pattern corresponding with the pigment pattern to be produced is formed in an electrophotographic way, and the electrostatic charge pattern is developed with nonvolatile powder particles that have the desired phosphorescent or luminescent properties.
• the photoconductive layer containing the phosphor powder image is heated in order to remove the volatile substances of the photoconductive recording layer and to make the phosphor pattern adhere to the screen support.
• thermolysable binding agent In order to fix the powder image before applying the heating step it is preferably overcoated with a layer of a thermolysable binding agent.
• the recording layer may further contain boric acid.
• the photoconductors mentioned in the French Patent Specification are advantageously partly or wholly substituted by the photoconductive substances applied according to the present invention.
• thermolysable binding agents belong to the class of the polyacrylic acid esters and polymethacrylic acid esters, e.g. polymethyl methacrylate, polyethyl methacrylate and polyethyl acrylate.
• the thickness of the photoconductive layers of the present invention is not critical but is open to choice within a wide range according to requirements in each individual case. Good results are attained with photoconductive layers of a thickness between 1 and 30 ,u preferably between 2 and 20 ,u. Too thin layers do not have a sufficient insulating power in the absence of active electromagnetic radiation, whereas too thick layers require extensive exposure times.
• a relatively conductive support for the recording layer is used, e.g., an electroconductive sheet or plate, or an insulating sheet or plate covered with an electroconductive interlayer.
• electro-conductive plate or sheet a plate or sheet those electrical resistivity is smaller than that of the non-irradiated (darkadapted) photoconductive layer, i.e., in general smaller than 10 ohm.cm and preferably is at least times as small as that of the recording layer. Supports whose resistivity is not higher than 10 ohm.cm are preferred.
• the recording layers themselves have preferably an electrical insulating power as high as possible without affecting too much the photosensitivity by means of too high an amount of insulating binding agent.
• the recording layers have in non-irradiated state (darkadapted state) a resistivity of at least 10 ohm.cm.
• Suitable conductive plates are, e.g., plates ofrnetals such as aluminium, zinc, copper, tin, iron, or lead.
• Suitable electro-conductive interlayers for insulating supports are, e.g., vacuum-coated metal and conductive metal compound (metal oxide or metal salt) layers such as silver, tin, aluminium, titanium dioxide and copper iodide conductive layers, transparent conductive polymer layers, e.g., applied from polymers containing quatemized nitrogen atoms, such as those described in the United Kingdom Pat. Specification 950,960 filed Sept. 23, 1960 by Gevaert Photo- Producten N.V., or layers containing conductive particles, e.g. carbon black and metal particles dispersed in a binder.
• the binder used for said particles has a resistivity preferably lower than l0 ohm.cm.
• a suitable binder for that purpose is gelatin.
• lt is possible to produce transparent photoconductive recording materials by applying the photoconductive compounds together with a suitable binder (if necessary) from a clear solution to a conductive transparent base or a transparent insulating base coated with an electroconductive transparent interlayer.
• resin sheets having an optical density of not more than 0.10 are preferred, e.g., a sheet made of polyethylene terephthalate or cellulose triacetate.
• the conductive interlayer preferably consists of a metal coating, e.g., a vacuum-coated aluminium layer having an optical density of not more than 0.30, or of a conductive transparent polymer layer composed, e.g., of an organic polyionic polymer, e.g., a polymer containing quatemized nitrogen atoms such as a quatemized polyethylene-imine.
• Paper sheets that have an insufficient electrical conductivity are coated or impregnated with substances enhancing their conductivity, e.g., by means of a conductive overcoat such as a metal sheet laminated thereto.
• antistatic agents of polyionic type e.g., CALGON CONDUCTIVE POLYMER 26l (trade mark of Calgon Corporation, Inc. Pittsburgh, Pa., USA.) for a so lution containing 39.1 percent by weight of active conductive solids, which contain a conductive polymer having recurring units of the following type:
• H36 CH3 Paper sheets are preferably impermeabilized to organic solvents, e.g., by means of a water-soluble colloid or by strongly hydrating the cellulose fibers such as in the case of glassine paper.
• the photoconductive substances involved preferably are first dissolved or dispersed in a suitable organic solvent such as a chlorinated hydrocarbon, e.g., methylene chloride.
• a suitable organic solvent such as a chlorinated hydrocarbon, e.g., methylene chloride.
• the solution or dispersion thus obtained is uniformly spread on a surface of a suitable support, e. g., by centrifuging, spraying, brushing, or coating. Thereupon the layer formed is dried in such a way that a solid photoconductive layer is formed on the surface of the support.
• Recording materials according to the present invention can be used in any of the different techniques known in recording with the aid of photoconductors. According to a preferred embodiment they are used in a technique based on the discharge of an electrostatically charged recording layer by exposure to light.
• Photoconductive recording materials prepared according to the present invention can be used in exposure units equipped with incandescent lamps, so that they need not be exposed with light rays rich in ultraviolet such as those emitted by a high-pressure mercury vapour bulb.
• the electrostatic charging of photoconductive recording elements according to the present invention can be effected according to any method known in electrophotography, e.g., by friction with a smooth material, with.a material possessing a high electric resistance, e.g., a cylinder coated with polystyrene, by corona discharge, by contact charge, or by discharge of a capacitor.
• Recording materials according the said organic photoconductive substances can be used in a recording technique comprising a' negative corona charging as well as in a recording technique comprising a positive corona charging.
• the electrostatic latent image can be converted into a visible image either on the electrophotographic material wherein the latent image was formed, or on a material to which the electrostatic latent image was transferred, e.g., by application of the method described in the Belgian Pat. Specification 529,234 filed May 29, 1954 by Chester Floyd Carlson.
• the conversion of the original or transferred latent image into a visible image can occur according to one of the techniques known in electrophotography, wherein use is made of a conductivity pattern (e.g., electrolysis) or the electrostatic attraction or repulsion of finely divided coloured substances, which, e.g., are present in a powder mixture, in an electrically insulating liquid (e.g., in the form of a suspension) or in a gas (e.g., in the form of an aerosol), or wherein electrostatic attraction is used for selectively wetting charged portions of the recording layer, as described in the United Kingdom Pat. Specifications 1,020,505 filed Nov. 8, 1961 and 1,033,419 filed Nov. 26, 1962 both by Gevaert Photo-Producten N.V.
• a conductivity pattern e.g., electrolysis
• electrostatic attraction or repulsion of finely divided coloured substances which, e.g., are present in a powder mixture, in an electrically insulating liquid (e.g., in the form
• a negative or a positive print can be obtained from any original. If both printing material and developing powder or developing liquid have the same sign of charge, the powder only adheres to the discharged areas so that a negative print is obtained. If the signs of the recording material and of the developing powder or developing liquid differ, a positive print is obtained.
• the visible image obtained can, if necessary, be fixed according to one of the methods known in electrophotography, e.g., by heating, or it can be transferred to another support, e.g., according to the method described in the United Kingdom Pat. Specification 658,699 filed Apr. 14, 1949 by Battelle Memorial Institute and fixed thereon.
• the present heterocyclic organic photoconductive compounds can also be supplied in a thermoplastic recording process to form a ripple-image as described, e.g., in the United Kingdom Pat. Specification 964,881
• the present invention by no means is limited to one or other particular embodiment of using the electrophotographic material containing the photoconductive compounds as described herein.
• the exposure technique, the charging method, the formation of the charge pattern, the transfer of such pattern if applied, the developing method, and the fixation or the transfer of the developing material pattern may be modified or adapted.
• composition of the recording materials used in these methods may be adapted to the requirements of the recording process used.
• Electrophotographic materials according to the present invention can be employed in reproduction techniques, wherein different kinds of electromagnetic radiations are used, e.g., visible light, U.V.-radiation, X- rays and y-rays.
• Example I To a polyethylene terephthalate support of p. a
• the charged recording layer was contactexposed for 30 see. through a step wedge of increment 0.2 with incandescent bulbs that together represent 100 Watt and were placed at a distance of 30 cm.
• the development was carried out by means of developing electrode placed at a distance of 3 mm from the material.
• the speed of the developed samples is expressed by the number of the steps that is not covered with developer material.
• Rhodamin B (C.l. Basic Violet; C.l. 45,170) having the following structural formula:
• the dried coating was negatively corona charged with a potential difference of 6,000 V between the corona wires and the ground.
• the charged recording layer was contact-exposed for 5 see. through a stepwedge having an increment 0.2 using tungsten filaments lamps that together represent Watt and were placed at a distance of 30 cm.
• Example 3 To the coating composition of Example 2, 0.25 g of 2,3-dicyano-p-quinone as chemical sensitizer and compound with strongly electronegative groups was added.
• the corona charging, image-wise exposure and development were the same as in Example 2.
• the speed of the recording layer was found to be 2.5 times higher than that of Example 2.
• R represents a (C -C alkyl radical, and 2, represents the necessary atoms to close an adjacent ring system of the fluorene series, and a spectral sensitizing agent.
• a method for recording and reproducing information comprising the steps of producing an electrostatic charge pattern by electrostatically charging and information-wise exposing to electromagnetic radiation a recording element containing a photoconductive compound corresponding to the following general formula:
• R represents a (C -C alkyl radical
• Z represents the necessary atoms to close an adjacent ring system of the fluorene series and a spectral sensitizing agent producing thereby an information-wise increase of the conductivity in the recording element, and developing the resulting latent electrostatic charge pattern with a substance that can be electrostatically attracted.
• the recording element is a recording layer that has been applied to a conductive layer or support having a resistivity lower than that of the dark adapted recording element.
• a photoconductive compound selected from the group of photoconductive selenium, and the photoconductive oxides, sulphides, and selenides, of zinc, cadmium, mercury, antimony, bismuth and lead.
• a recording material containing a photoconductive insulating recording element capable of being electrostatically charged in the absence of activating electromagnetic radiation and capable of retaining the applied charge for a period of time long enough to produce thereon a developed electrostatic charge pattern, characterized in that the recording element stands in electroconductive relationship to a layer or support with a lower resistivity than the recording element and in that the recording element contains an organic photoconductive compound corresponding to the following general formula:
• R represents a (C -C alkyl radical, and 2, represents the necessary atoms to close an adjacent ring system of the fluorene series and a spectral sensitizing agent. 17.
• a recording material according to claim 19, wherein the support is an insulating transparent resin support coated with a transparent electroconductive interlayer.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Photoreceptors In Electrophotography (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Quinoline Compounds (AREA)

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• 1970
  • 1970-12-11 GB GB5909470A patent/GB1379387A/en not_active Expired
• 1971
  • 1971-11-24 FR FR7142346A patent/FR2117141A5/fr not_active Expired
  • 1971-11-25 BE BE775786A patent/BE775786A/nl unknown
  • 1971-12-02 DE DE19712159804 patent/DE2159804A1/de active Pending
  • 1971-12-07 IT IT86286/71A patent/IT943538B/it active
  • 1971-12-08 BE BE776380A patent/BE776380A/nl unknown
  • 1971-12-08 DE DE19712160873 patent/DE2160873A1/de active Pending
  • 1971-12-10 US US00206901A patent/US3830647A/en not_active Expired - Lifetime
  • 1971-12-10 US US00206872A patent/US3832171A/en not_active Expired - Lifetime

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