US3877936A - Photoconductive copolymer of N-vinylcarbazole and N-vinylphthalimide - Google Patents

Photoconductive copolymer of N-vinylcarbazole and N-vinylphthalimide Download PDF

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US3877936A
US3877936A US342646A US34264673A US3877936A US 3877936 A US3877936 A US 3877936A US 342646 A US342646 A US 342646A US 34264673 A US34264673 A US 34264673A US 3877936 A US3877936 A US 3877936A
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Prior art keywords
vinylphthalimide
vinylcarbazole
structural units
imaging member
mole percent
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US342646A
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English (en)
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William W Limburg
Donald A Seanor
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Xerox Corp
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Xerox Corp
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Priority to US342646A priority Critical patent/US3877936A/en
Priority to CA192,004A priority patent/CA1024696A/en
Priority to DE2409108A priority patent/DE2409108A1/de
Priority to AU66637/74A priority patent/AU485388B2/en
Priority to IT12600/74A priority patent/IT1010697B/it
Priority to GB1156974A priority patent/GB1444048A/en
Priority to BR742072A priority patent/BR7402072D0/pt
Priority to ES424411A priority patent/ES424411A1/es
Priority to JP49030855A priority patent/JPS5233495B2/ja
Priority to BE142114A priority patent/BE812436A/xx
Priority to FR7409307A priority patent/FR2223400B1/fr
Priority to NL7403708A priority patent/NL7403708A/xx
Priority to US05/517,122 priority patent/US3970602A/en
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    • 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
    • G03G5/07—Polymeric photoconductive materials
    • G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G5/072—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups
    • G03G5/073—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups comprising pending carbazole groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F26/12—N-Vinyl-carbazole

Definitions

  • ABSTRACT Polymeric compositions comprising the product of the addition polymerization of N-vinylcarbazole and at least one member selected from the group consisting of N-vinylphthalimide and the isostructural modifications thereof.
  • Many of the above polymeric products are photoconductive and, thus, are suitable for use in electrophotography.
  • this invention involves random copolymers, many of which are photoconductive and. thus, suitable for use in electrophotographic imaging members and processes.
  • the spacial constraint and relative conformation of the functional groups of the two principal components of these compositions apparently favors a charge transfer interaction between them.
  • the developed image can then be read or permanently affixed to the photoconductor where the imaging layer is not to be reused.
  • This latter practice is usually followed with respect to the binder-type photoconductive films (e.g. ZnO) where the photoconductive imaging layer is also an integral part of the finished copy.
  • the latent image can be developed on the imaging surface of a reusable photoconductor or transferred to another surface, such as a sheet of paper, and thereafter developed.
  • the latent image is developed on the imaging surface of a reusable, photoconductor, it is subsequently transferred to another substrate and then permanently affixed thereto.
  • Any one of a variety of well known techniques can be used to permanently affix the toner image to the copy sheet, including overcoating with transparent films, and solvent or thermal fusion of the toner particles to the supportive substrate.
  • the materials used in the photoconductive layer should preferably be capable of rapid switching from insulative to conductive to insulative state in order to permit cyclic use of the imaging surface.
  • the failure of a material to return to its relatively insulative state prior to the succeeding charging sequence will result in an increase in the dark decay rate of the photoconductor.
  • This phenomenon commonly referred to in the art as fatigue, has in the past been avoided by the selection of photo conductive materials possessing rapid switching capacity.
  • Typical of the materials suitable for use in such a rapidly cycling system include anthracene, sulfur. selenium and mixtures thereof (U.S. Pat. No. 2,297,691); selenium being preferred because of its superior photosensitivity.
  • poly(N- vinylcarbazole) have been the focus of increasing interest in electrophotography. Most organic photoconductive materials, including poly(N-vinylcarbazole), lack the inherent photosensitivity to be competitive with selenium. This need for the enhancement of the photoresponse characteristics or organic photoconductors thus led to the formulation of these organic materials with other compounds, commonly referred to as activators.”
  • poly( vinylcarbazoles) for example, when sensitized with 2,4,7-trinitro-9-fluorenone exhibit good photoresponse and discharge characteristics and, (depending upon the polarity of the surface charge), low dark decay; U.S. Pat. No. 3,484,237.
  • the concentration of activator capable of formulation with the above materials is finite; generally being limited to less than 10 weight percent of the composition.
  • concentration of activator capable of formulation with the above materials is finite; generally being limited to less than 10 weight percent of the composition.
  • the addition of high loadings of activator to many of the above materials will lead to impairment of mechanical and/or the photoconductive properties of the sensitized composition.
  • the excessive addition of activators to both the photoconductive and nonphotoconductive materials of the types disclosed in the above patents will result in crystallization of these activators, thus impairing the mechanical strength and other physical properties of the resultant photoconductive composition.
  • Still yet other sensitizers, when present in relatively low concentration can result in over sensitization of the composition in that the photocurrent generated upon exposure will persist long after illumination ceases, BUL. CHEM. SOC. of .lAP.
  • the object of this invention to provide polymeric compositions wherein the structural units thereof are from at least two vinyl monomers, one having an electron donor and a second having and electron acceptor function. More specifically, the principal object of this invention is to provide a photoconductive composition having an electron donor and an electron acceptor function.
  • a polymeric composition comprising structural units from (i) N-vinylcarbazole and (ii) at least one member selected from the group consisting of N- vinylphthalimide and the isostructural modifications thereof. Since the principal area of proposed utility of the above composition resides in the electrophotographic arts, the preferred compositions are photoconductive; the carbazole moiety providing the electron donor function and the phthalimide moiety providing the electron acceptor function. These preferred copolymers will generally contain from about 50-90 mole percent structural units from N-vinylcarbazole and from about to about 50 mole percent structural units from N-vinylphthalimide.
  • FIG. 1 is a graphic illustration of the log of photocurrent vs. wavelength applied light for two of the copolymers of this invention and poly-N-vinylcarbazole. In each instance, the photoresponse was measured under an applied positive potential.
  • FIG. 2 is a similar graphical illustration of photocurrent vs. wavelength for these same compositions when under an applied negative potential.
  • FIG. 3 is a graphical illustration of the charge transfer band of the preferred photoconductive composition of this invention.
  • the vinyl monomers should preferably be purged of impurities. With respect to N- vinylcarbazole, this is achieved by vacuum sublimation, or by recrystallization of this monomer from methanol under nonoxidizing conditions.
  • the N- vinylphthalimide monomer can be purified by passing a benzene solution thereof through a Woelm neutral aluminua column, followed by recrystallization from benzene. Subsequent to recovery of the above purified monomers they can be formed into the polymeric compositions of this invention by standard free radical initiated addition polymerization techniques. It is generally preferred that the above monomers be reacted with one another under conditions which favor formation of copolymers having substantially the same mole ratio with respect to its structural units as the concentration of monomers in the charge.
  • a copolymer containing about 9 mole percent structural units from N-vinylphthalimide and about 91 mole percent structural units from N-vinylcarbazole can be prepared according to the following procedure. About 0.866 grams (0.005 moles) of N-vinylphthalimide and 9.16 grams (0.05 moles) of N-vinylcarbazole are dissolved in 25 milliliters anhydrous benzene. The monomer solution is then transferred to a 50 milliliter polymer tube. A free radical initiator, such as azobisisobutyronitrile, is then introduced into the solution.
  • a free radical initiator such as azobisisobutyronitrile
  • initiator Generally about 0.03 grams (1.8 X 10- 4 moles) initiator is adequate to facilitate substantially complete copolymerization of the two monomeric materials.
  • the monomer solution is degassed three times by conventional freeze-thaw methods and then the tube sealed under a vacuum.
  • the sealed polymer tube is then placed in a constant temperature bath at 75C and allowed to remain there for about 12 hours. During this interval, the contents of the tube develop a yellowish color.
  • the tube is then removed from the constant temperature bath, cooled, the seal broken and the polymeric product separated from the reaction medium by precipitation with hexane. This precipitation is generally carried out by continuous agitation of the hexane-polymer slurry ina Waring blender.
  • the crude polymeric product is purified by redissolving it in a minimum amount of a mixture of benzene/tetrahydrofuran 1:2 by volume) and then reprecipitated from hexane.
  • the recovered polymeric solids are then redissolved and precipitated as described above three additional times.
  • the polymer solids thus produced have a pale yellow tint and display a yellow-green fluorescence when observed under ultraviolet light.
  • the polymer solids are dried overnight in a vacuum oven at about C. Further analysis of the polymeric solids indicates that the relative concentration of carbazole and phthalimide functional units of thecopolymer are substantially the same as the gross mole composition of the monomer charge. Molecular weight determinations were made by standard vapor pressure osmometry techniques and indicate that the polymeric product has a number average molecular weight of 100,000.
  • Additional polymeric compositions were prepared according to the above technique from monomer charges containing one mole percent N- vinylphthalimide and 99 mole percent N- vinylcarbazole; 25 mole percent N-vinylphthalimide and percent N-vinylcarbazole; 50 mole percent N- vinylphthalimide and 50 mole percent N- vinylcarbazole; 75 percent N-vinylphthalimide and percent N-vinylcarbazole; and 99 percent N- vinylphthalimide and and one mole percent N- vinylcarbazole.
  • the polymeric compositions thus prepared substantially reflected the relative concentration of the individual monomers in the charge.
  • Other physical properties were also substantially the same as that reported for the above described composition.
  • This intensity is assumed to be a function of the high concentration of the charge transfer complex in solution brought about by the forced interaction between adjacent donor and acceptor sites on the common polymeric backbone. This difference in electronic properties is illustrated graphically by FIG. 3. The intensity of this band remained unchanged even where solvents of different dielectric constants were used. All the evidence, thus, supports the assumption that this broad charge transfer band is predominently attributable to a nondissociable intramolecular interaction. That is to say that charge transfer interaction is taking place predominently within the diads formed by adjacent donor and acceptor sites on common polymeric strands.
  • the above polymeric compositions can be formed into photoconductive films useful in electrophotography by simple solvent casting and coating techniques.
  • an imaging member useful in electrophotography can be prepared from the polymeric compositions of this invention by draw coating a 20 weight percent solution of one of the above compositions on an aluminized Mylar substrate.
  • Typical of the solvents which can be used as the vehicle in such a draw coating process are tetrahydrofuran and mixtures of toluenecyclohexanone (:60 by volume).
  • the film thickness is controlled by adjustment of the viscosity of the coating solution and/or by mechanical means.
  • a photoconductive layer prepared as thus described should have a thickness in the range of from about 5 to about 50 microns in order to be suitable for use in an electrophotographic imaging member.
  • any conductive substrate traditionally used in electrophotography will provide a suitable ground plane for the photoconductive imaging layer.
  • a barrier layer may, if desired, be interfaced between the photoconductive layer and the conductor substrate in order to further reduce the rate of dark decay of the imaging member. Any of the organic or inorganic materials disclosed in Dessauer, US. Pat. No. 2,901,348 can be used as the material for this barrier layer.
  • a series of electrophotographic imaging members are prepared as described above.
  • the thickness of the photoconductive imaging layer is about 15 microns.
  • an additional imaging member is prepared from a homopolymer of poly-N- vinylcarbazole. In each instance, the imaging member is corona charged in the dark to a positive potential of about 600 volts and then exposed continuously to white light from a 200 watt tungsteniodine lamp from a distance of 15 centimeters. In each instance the time required to fully discharge the plate is noted.
  • the imaging member having a photoconductive layer comprising about I mole percent structural units from N-vinylphthalimide and 99 mole percent structural units from N-vinylcarbazole fully discharges a positive charge in about one-third the time required to fully discharge a negative charge.
  • the imaging members having a photoconductive layer comprising from about 10 to about 50 mole percent structural units from N-vinylphthalimide are capable of complete discharge of both positive and negative potentials in substantially the same times.
  • the time required to discharge the imaging members having photoconductive layers prepared from the compositions of this invention were substantially less than the time required to discharge the imaging member having a photoconductive layer of poly-N- vinylcarbazole.
  • the imaging members are then further evaluated in order to determine the initial rate of discharge of the photoconductive layer under continuous white light illumination.
  • the result of this evaluation is summarized in the Table presented below:
  • FIG. 1 provides the action spectrum for all three of these imaging members when placed under an applied positive potential.
  • FIG. 2 provides a similar basis for comparison when these same imaging members are under an applied negative potential.
  • the maximum photoresponse of all three of the compositions appears at a wavelength of about 3680 A; however, only the imaging members having photoconductive layers prepared from the compositions of this invention tail off well into the visible portion of the spectrum. A comparison of FlGS.
  • Example II The procedure of Example I is repeated except for the substitution of a copolymer comprising about 25 mole percent structural units from N-vinylphthalimide and about 75 mole percent structural units from N- vinylcarbazole.
  • N-vinyltetrahalophthalimide/N-vinylcarbazole copolymers can be prepared by combining 0.45 grams of a copolymer comprising vinylamine/N-vinylcarbazole (9.2/90.8 mole percent) and about 0.001 mole of tetrahalophthalic anhydride in 100 milliliters of cyclohexanone. This solution is prepared in a 250 milliliter flask equipped with a magnetic stirring bar and reflux condenser. After the above ingredients are dissolved, a few drops of triethylamine catalyst are added to the solution and the contents of the flask heated to boiling under reflux conditions.
  • Heating continues for a period of about 2 days, after which time the colorless absorption will take on a yellow, yellow-orange, orange or light red color depending upon the anhydride in the solution.
  • the solution is now allowed to cool to room temperature, and the polymer separated by precipitation from methanol in a Waring blender. Where the polymer forms a fine flocculent, separation may require centrifugation.
  • the various isostructural modifications of N-vinylphthalimide/N-vinylcarbazole exhibit maximum adsorption at about 350 nanometers and tail off well into the visible band of the spectrum.
  • the flask containing the solution is then heated over a steam bath for about l V; hours at which time the polymer precipitated from the DMF by the addition of water.
  • the precipitate is separated from the solution by filtration and purified by washing with warm dilute aqueous potassium hydroxide solution. This washing procedure is repeated several times until the filtrate is colorless.
  • the polymer is then dried in a vacuum oven at about 70C.
  • the number average molecular weight of the product is in the range of about 100,000.
  • EXAMPLE V Preparation of N-vinyl-4-nitroaniline/N- vinylcarbazole copolymer about 1.5 grams of a polymer comprising vinylamine/N-vinylcarbazole (/75 mole percent) is dissolved in 50 milliliters of dimethyl formamide (DMF). The reaction vessel containing this solution is purged of air with nitrogen and the remainder of the reaction carried out under this nitrogen blanket. About 0.27 grams potassium carbonate is suspended in this solution and l thereafter one milliliter of l-fluoro-4-nitrobenzene .added by dropwise addition. The resulting mixture is heated over a steam bath for about 22 hours, the polymer precipitated from the DMF by the addition of about 200 milliliters of water.
  • DMF dimethyl formamide
  • the precipitate separated from the solution by filtration In order to assist in the separation of the polymer from the solution, a small amount of ammonium chloride was added to assist in coagulation of the polymer.
  • the isolated polymer is washed repeatedly with dilute aqueous sodium hydroxide and then dried in a vacuum oven at about C.
  • the number average molecular weight of the polymeric composition is in the range of about 93,000.
  • Example VI The procedures of Example VI and V are repeated except for the use of a copolymer comprising 9.2 mole percent structural units of vinylamine and 90.8 mole percent structural units of N-vinylcarbazole.
  • a number of the polymeric compositions of the previous examples are evaluated with respect to their photoconductivity by first forming them into an imaging layer on an aluminized Mylar substrate as previously described and then subjecting the resulting imaging member to standard electrophotographic analysis.
  • An imaging member useful in electrophotography comprising a conductive substrate and overlying at least one surface of said substrate a substantially continuous polymeric photoconductive film comprising a copolymer having structural units from (i) N- vinylcarbazole and (ii) N-vinylphthalimide.
  • the imaging member of claim 1 wherein the photoconductive film comprises a copolymer containing from about to about 50 mole percent structural units from N-vinylphthalimide.
  • the imaging member of claim 1 wherein the photoconductive film comprises a copolymer containing from about to about 50 mole percent structural units from N-vinylphthalimide.
  • An imaging member useful in electrophotography comprising a conductive substrate and overlying at least one surface of said substrate a substantially continuous polymeric photoconductive film comprising a copolymer having structural units from (i) N- vinylcarbazole and (ii) N-vinylphthalimide or the chloro-substituted isostructural modifications thereof.
  • the imaging member of claim 4 wherein the polymeric photoconductive film comprises a copolymer containing from about 10 to about 50 mole percent structural units from N-vinylphthalimide or the chlorosubstituted isostructural modifications thereof.
  • the imaging member of claim 4 wherein the photoconductive film comprises a copolymer containing from about 25 to about 50 mole percent structural units from N-vinylphthalimide or the chlorosubstituted isostructural modifications thereof.
  • An imaging member useful in electrophotography comprising a conductive substrate and overlying at least one surface of said substrate a substantially continuous polymeric photoconductive film comprising a copolymer having structural units from (i) N- vinylcarbazole (ii) N-vinylphthalimide or the bromosubstituted isostructural modifications thereof.
  • the photoconductive film comprises a copolymer containing from about 10 to about 50 mole percent structural units from N-vinylphthalimide or the bromosubstituted isostructural modifications thereof.
  • the photoconductive film comprises a copolymer containing from about 25 to about 50 mole percent structural units from N-vinylphthalimide or the bromosubstituted isostructural modifications thereof.
  • An imaging member useful in electrophotography comprising a conductive substrate and overlying at least one surface of said substrate a substantially continuous polymeric photoconductive film comprising a copolymer containing structural units from (i) N- vinylcarbazole and (ii) N-vinylphthalimide or the iodosubstituted isostructural modifications thereof.
  • the photoconductive film comprises a copolymer containing from about 10 to about 50 mole percent structural units from N-vinylphthalimide or the iodo-substituted isostructural modifications thereof.
  • the photoconductive film comprises a copolymer containing from about '25 to about 50 mole percent structural units from N-vinylphthalimide or the iodo-substituted isostructural modifications thereof.
  • An imaging member useful in electrophotography comprising a conductive substrate and overlying at least one surface of said substrate a substantially continuous polymeric photoconductive film comprising a copolymer containing structural unites from (i) N-vinylcarbazole and (ii) a nitro-substituted N-vinylaniline.
  • the imaging member of claim 13 wherein the photoconductive film comprises a copolymer containing from about 10 to about 50 mole percent structural units from a nitro-substituted N-vinylaniline.
  • the photoconductive film comprises a copolymer containing from about 25 to about 50 mole percent structural units from a nitro-substituted N-vinylaniline.

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  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
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US342646A 1973-03-19 1973-03-19 Photoconductive copolymer of N-vinylcarbazole and N-vinylphthalimide Expired - Lifetime US3877936A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US342646A US3877936A (en) 1973-03-19 1973-03-19 Photoconductive copolymer of N-vinylcarbazole and N-vinylphthalimide
CA192,004A CA1024696A (en) 1973-03-19 1974-02-07 Photoconductive copolymer compositions
DE2409108A DE2409108A1 (de) 1973-03-19 1974-02-26 Polymere massen
AU66637/74A AU485388B2 (en) 1974-03-14 random COPOLYMERS
GB1156974A GB1444048A (en) 1973-03-19 1974-03-15 Random copolymers
IT12600/74A IT1010697B (it) 1973-03-19 1974-03-15 Composizione polimerica partico larmente per l elemento d immagi ne di una macchina copiatrice elettrostatografica e procedimen to per la foramzione e lo sviluppo di detta immagine
BR742072A BR7402072D0 (pt) 1973-03-19 1974-03-18 Um copolimero fotocondutor, uma pelicula polimerica substancialmente continua, um membro de formacao de imagem, e um processo de formacao de imagem eletrostatografica
ES424411A ES424411A1 (es) 1973-03-19 1974-03-18 Un metodo electrostatografico de formacion de imagenes.
JP49030855A JPS5233495B2 (it) 1973-03-19 1974-03-18
BE142114A BE812436A (fr) 1973-03-19 1974-03-18 Copolymeres de n-vinylcarbazole et de n-vinylphtalimide ou de ses modifications isostructurales
FR7409307A FR2223400B1 (it) 1973-03-19 1974-03-19
NL7403708A NL7403708A (it) 1973-03-19 1974-03-19
US05/517,122 US3970602A (en) 1973-03-19 1974-10-23 Copolymers of N-vinylcarbazole and N-vinylphthalimide and derivatives thereof

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US342646A US3877936A (en) 1973-03-19 1973-03-19 Photoconductive copolymer of N-vinylcarbazole and N-vinylphthalimide

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US05/517,122 Division US3970602A (en) 1973-03-19 1974-10-23 Copolymers of N-vinylcarbazole and N-vinylphthalimide and derivatives thereof

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JP (1) JPS5233495B2 (it)
BE (1) BE812436A (it)
BR (1) BR7402072D0 (it)
CA (1) CA1024696A (it)
DE (1) DE2409108A1 (it)
ES (1) ES424411A1 (it)
FR (1) FR2223400B1 (it)
GB (1) GB1444048A (it)
IT (1) IT1010697B (it)
NL (1) NL7403708A (it)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4898915A (en) * 1983-08-24 1990-02-06 University Of Akron Alternating copolymerization of donor monomers having protected amine groups with acceptor monomers
US5326661A (en) * 1991-11-13 1994-07-05 Hoechst Celanese Corp. Photorefractive polymers containing discrete photoconductive and electrooptical units
US5980775A (en) * 1996-11-26 1999-11-09 Cabot Corporation Composition and slurry useful for metal CMP
US20090087763A1 (en) * 2007-09-27 2009-04-02 Weiss David S Photoconductors containing n-arylphthalimides

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Publication number Priority date Publication date Assignee Title
US3073785A (en) * 1959-07-02 1963-01-15 Electrically conductive polymeric
US3155503A (en) * 1959-02-26 1964-11-03 Gevaert Photo Prod Nv Electrophotographic material
US3232755A (en) * 1959-07-01 1966-02-01 Azoplate Corp Photoconductive layers for electrophotographic purposes
US3287122A (en) * 1961-07-24 1966-11-22 Azoplate Corp Process for the sensitization of photoconductors
US3418116A (en) * 1963-02-21 1968-12-24 Matsushita Electric Industrial Co Ltd Electrophotographic materials comprising polymeric intramolecular charge transfer complexes
US3697264A (en) * 1970-03-02 1972-10-10 Richard M Podhajny Novel photoconductive carbazole polymers and photoconductive elements embodying same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3155503A (en) * 1959-02-26 1964-11-03 Gevaert Photo Prod Nv Electrophotographic material
US3232755A (en) * 1959-07-01 1966-02-01 Azoplate Corp Photoconductive layers for electrophotographic purposes
US3073785A (en) * 1959-07-02 1963-01-15 Electrically conductive polymeric
US3287122A (en) * 1961-07-24 1966-11-22 Azoplate Corp Process for the sensitization of photoconductors
US3418116A (en) * 1963-02-21 1968-12-24 Matsushita Electric Industrial Co Ltd Electrophotographic materials comprising polymeric intramolecular charge transfer complexes
US3697264A (en) * 1970-03-02 1972-10-10 Richard M Podhajny Novel photoconductive carbazole polymers and photoconductive elements embodying same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4898915A (en) * 1983-08-24 1990-02-06 University Of Akron Alternating copolymerization of donor monomers having protected amine groups with acceptor monomers
US5326661A (en) * 1991-11-13 1994-07-05 Hoechst Celanese Corp. Photorefractive polymers containing discrete photoconductive and electrooptical units
US5980775A (en) * 1996-11-26 1999-11-09 Cabot Corporation Composition and slurry useful for metal CMP
US20090087763A1 (en) * 2007-09-27 2009-04-02 Weiss David S Photoconductors containing n-arylphthalimides
US7732116B2 (en) * 2007-09-27 2010-06-08 Eastman Kodak Company Photoconductors containing N-arylphthalimides

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CA1024696A (en) 1978-01-17
FR2223400A1 (it) 1974-10-25
IT1010697B (it) 1977-01-20
BR7402072D0 (pt) 1974-12-24
AU6663774A (en) 1975-09-18
GB1444048A (en) 1976-07-28
ES424411A1 (es) 1976-11-01
JPS50111189A (it) 1975-09-01
FR2223400B1 (it) 1977-06-17
JPS5233495B2 (it) 1977-08-29
NL7403708A (it) 1974-09-23
BE812436A (fr) 1974-07-15
DE2409108A1 (de) 1974-09-26

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