Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C247/00—Compounds containing azido groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
• • 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
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0605—Carbocyclic compounds
  • G03G5/0607—Carbocyclic compounds containing at least one non-six-membered ring
• • 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
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
• • 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
  • G03G5/0627—Heterocyclic compounds containing one hetero ring being five-membered
  • G03G5/0629—Heterocyclic compounds containing one hetero ring being five-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
  • G03G5/0624—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

Definitions

• This invention relates to electrophotography, and in particular to photoconductive compositions and elements.
• the process of xerography employs an electrophotographic element comprising a support material bearing a coating of a normally insulating material whose electrical resistance varies with the amount of incident actinic radiation it receives during an imagewise exposure.
• the element commonly termed a photoconductive element, is first fiiven a uniform surface charge, generally in the dark after a suitable period of dark adaptation. It is then exposed to a pattern of actinic radiation which has the effect of differentially reducing the potential of the surface charge in accordance with the relative energy contained in various parts of the radiation pattern.
• the differential surface charge or electrostatic latent image remaining on the electrophotographic element is then made visible by contacting the surface with a suitable electroscopic marking material.
• marking material or toner whether contained in an insulating liquid or on a dry carrier, can be deposited on the exposed surface in accordance with either the charge pattern or in the absence of charge pattern as desired.
• the deposited marking material can then be either permanently fixed to the surface of the sensitive element by known means such as heat, pressure, solvent vapor, or the like, or transferred to a second element to which it can similarly be fixed.
• the electrostatic latent image can be transferred to a second element and developed there.
• Various photoconductive insulating materials have been employed in the manufacture of electrophotographic elements. For example, vapors of selenium and vapors of selenium alloys deposited on a suitable support and particles of photoconductive zinc oxide held in a resinous, film-forming binder have found wide application in present-day document copying applications.
• compositions when coated as a film or layer on a suitable support also yield an element which is reusable; that is, it can be used to form subsequent images after residual toner from prior images has been removed by transfer and/or cleaning.
• electrophotographic elements having coated thereon organic photoconductive compositions containing non-ionic cycloheptenyl compounds as photoconductors.
• the cycloheptenyl compounds can be substituted, if desired, in the nucleus with a wide variety of substituents such as (a) an aryl radical including substituted as well as unsubstituted aryl radicals, (b) a hydroxy radical, (c) an azido radical, (d) a heterocyclic radical having 5 to 6 atoms in the heterocyclic nucleus and at least one hetero nitrogen atom, and including substituted and unsubstituted hererocyclic radicals, and (e) an oxygen linked cycloheptenyl moiety.
• substituents such as (a) an aryl radical including substituted as well as unsubstituted aryl radicals, (b) a hydroxy radical, (c) an azido radical, (d) a heterocyclic radical having 5 to 6 atoms in the heterocyclic nucleus and at least one hetero nitrogen atom, and including substituted and unsubstituted hererocyclic radicals, and (
• the substitution on the cycloheptenyl nucleus occurs on an unsaturated carbon atom (i.e., a carbon atom having at least a double bond) when the cycloheptenyl moiety is a conjugated triene with no aromatic structure fused thereto. However, if there is at least one aromatic structure fused to the cycloheptenyl moiety, then the substituents are attached to a saturated carbon atom (i.e., a carbon atom with no double bonds).
• the preferred photoconductors of this invention are represented by the following structures:
• E and G can be either:
• D can be any of the substituents defined for E and G above and is attached to a carbon atom in the cycloheptenyl nucleus having adouble bond; (R and R (R 3 and R (R and R and (R and R are together the necessary atoms to complete a benzene ring fused to the cycloheptenyl nucleus.
• Some typical photoconductors of this invention are:
• Electrophotographic elements of the invention can be prepared with the photoconducting compounds of the invention in the usual manner, i.e., by blending a dispersion or solution of a photoconductive compound together with a binder, when necessary or desirable, and coating or forming a self-supporting layer with the photoconductor-containing material. Mixtures of the photoconductors described herein can be employed. Likewise, other photoconductors known in the art can be combined with the present photoconductors. In addition, supplemental materials useful for changing the spectral sensitivity or electrophotosensitivity of the element can be added to the composition of the element when it is desirable to produce the characteristic effect of such materials.
• Sensitizing compounds useful with the photoconductive compounds of the present invention can include a wide variety of substances such as pyrylium, thiapyrylium, and selenapyrylium salts of US. Pat. 3,250,615, issued May 10, 1966; fluorenes, such as 7,12-dioxo-13- dibenzo(a,h)fluorene, 5,10-dioxo 4a,11 diazabenzo(b) fluorene, 3,13-dioxo-7-oxadibenzo(b,g)fluorene, trinitrofluorenone, tetranitrofluorenone and the like; aromatic nitro compounds of US. Pat. 2,610,120; anthrones of US. Pat.
• sensitizing compound is to be used within a photoconductive layer as disclosed herein it is conventional practice to mix a suitable amount of the sensitizing compounds with the coating composition so that, after thorough mixing, the sensitizing compound is uniformly distributed throughout the desired layer of the coated element.
• no sensitizing compound is needed for the layer to exhibit photoconductivity.
• the lower limit of sensitizer required in a particular photoconductive layer is, therefore, zero.
• relatively minor amounts of sensitizing compound give substantial improvement in the electrophotographic speed of such layers, the use of some sensitizer is preferred.
• the amount of sensitizer that can be added to a photoconductor-incorporating layer to give effective increases in speed can vary Widely.
• any given case will vary with the specific photoconductor and sensitizing compound used. In general, substantial speed gains can be obtained where an appropriate sensitizer is added in a concentration range from about 0.0001 to about 30 percent by weight based on the weight of the film-forming coating composition. Normally, a sensitizer is added to the coating composition in an amount by weight from about 0.005 to about 5.0 percent by weight of the total coating composition.
• Preferred binders for use in preparing the present photoconductive layers are film-forming polymeric binders having fairly high dielectric strength which are good electrically insulating film-forming vehicles.
• Mater als of this type comprise styrene-butadiene copolymers; silicone resins; styrene-alkyd resins; silicone-alkyl resins; soyaalkyl resins; poly(vinyl chloride); poly(vinylidene chloride; vinylidene chloride-acrylonitrile copolymers; poly- (vinyl acetate); vinyl acetate-vinyl chloride copolymers; p'oly(vinyl acetals), such as poly(vinyl butyral); polyacrylic and methacrylic ester, such as poly(methylmethacrylate), poly(n-butylmethacrylate), poly(isobutyl meth acrylate), etc.; polystyrene; nitrated polystyrene; poly
• styrene-alkyd resins can be prepared according to the method described in U.S. Pats. 2,361,019 and 2,258,423.
• Suitable resins of the type contemplated for use in the photoconductive layers of the invention are sold under such tradenames as Vital PE-101, Cyrnac, Piccopale 100, Saran 1 -220 and Lexan 105.
• Other types of binders which can be used in the photoconductive layers of the invention include such materials as paraffin mineral Waxes, etc.
• Solvents of choice for preparing coating compositions of the present invention can include a number of solvents such as benzene, toluene, acetone, Z-butanone, chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, etc., ethers, e.g., tetrahydrofuran, or mixtures of these solvents, etc.
• solvents such as benzene, toluene, acetone, Z-butanone, chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, etc., ethers, e.g., tetrahydrofuran, or mixtures of these solvents, etc.
• the photoconductor substance is present in an amount equal to at least about 1 weight percent of the coating composition.
• the upper limit in the amount of photoconductor substance present can be widely varied in accordance with usual practice. In those cases where a binder is employed, it is normally required that the photoconductor substance be present in an amount from about 1 weight percent of the coating composition to about 99 weight percent of the coating composition.
• a preferred weight range for the photoconductor substance in the coating composition is from about 10 weight percent to about 60 weight percent.
• Coating thicknesses of the photoconductive composition on a support can vary widely. Normally, a coating in the range of about 0.001 inch to about 0.01 inch before drying is useful for the practice of this invention. The preferred range of coating thickness was found to be in the range from about 0.002 inch to about 0.006 inch before drying although useful results can be obtained outside of this range.
• Suitable supporting materials for coating the photoconductive layers of the present invention can include any of a wide variety of electrically conducting supports, for example, paper (at a relative humidity above 20 percent); aluminum-paper laminates; metal foils such as aluminum foil, zinc foil, etc.; metal plates, such as aluminum, copper, zinc, brass, and galvanized plates; vapor deposited metal layers such as silver or aluminum and the like.
• An especially useful conducting support can be prepared by coating a support material such as polyethylene terephthalate with a layer containing a semiconductor dispersed in a resin. Such conducting layers both with and without insulating barrier layers are described in US. Pat. 3,245,833.
• a suitable conducting coating can be prepared from the sodium salt of a carboxyester lactone of maleic anhydride and a vinyl acetate polymer.
• Such kinds of conducting layers and methods for their optimum preparation and use are disclosed in US. Pats. 3,007,901 and 3,267,807.
• the elements of the present invention can be employed in any of the well-known electrophotographic processes which require photoconductive layers.
• One such process is the aforementioned xerographic process.
• the electrophotographic element is given a blanket electrostatic charge by placing the same under a corona discharge which serves to give a uniform charge to the surface of the photoconductive layer. This charge is retained by the layer owing to the substantial insulating property of the layer, i.e., the low conductivity of the layer in the dark.
• the electrostatic charge formed on the surface of the photoconducting layer is then selectively dissipated from the surface of the layer by exposure to light through an image-bearing trans parency by a conventional exposure operation such as, for example, by contact-printing technique, or by lens projection of an image, etc., to form a latent image in the photoconducting layer.
• a conventional exposure operation such as, for example, by contact-printing technique, or by lens projection of an image, etc.
• the developing electrostatically attractable particles can be in the form of a dust, e.g., powder, pigment in a resinous carrier, i.e., toner, or a liquid developer may be used in which the developing particles are carried in an electrically insulating liquid carrier.
• a dust e.g., powder
• a resinous carrier i.e., toner
• a liquid developer may be used in which the developing particles are carried in an electrically insulating liquid carrier.
• the present invention is not limited to any particular mode of use of the new electrophotographic materials, and the exposure technique, the charging method, the transfer (if any), the developing method, and the fixing method as Well as the materials used in these methods can be selected and adapted to the requirements of any particular technique.
• Electrophotographic materials according to the present invention can be applied to reproduction techniques wherein different kinds of radiations, i.e., electromagnetic radiations as well as nuclear radiations, can be used. For this reason, it is pointed out herein that although materials according to the invention are mainly intended for use in connection with methods comprising an exposure,
• EXAMPLE 7 Preparation of ,N,N diethyl-3-methyl-4-[S-(SH-dibenzo- [a,d]cycloheptenyl)laniline and 4-[5 (5H dibenzo- [a,d] cycloheptenyl) ]-1-dimethylamino naphthalene
• S-(SH-dibenzo- [a,d]cycloheptenyl)laniline and 4-[5 (5H dibenzo- [a,d] cycloheptenyl) ]-1-dimethylamino naphthalene These compounds are prepared by the method of Example 6 using N,N-diethyl 3-methyl aniline and 1-dimethylamino naphthalene, respectively, in the alkylation reaction in place of N,N-din1ethyl aniline.
• EXAMPLE 10 Preparation of 3-(4-diethylamino-2-methylphenyl) cycloheptatriene Alkylation of N,N-diethyl-m-toluidine with tropylium tetrafluoroborate is carried out substantially by the procedure described in Example 9 to produce an 83 percent yield of product boiling at 1346 C./ 0.08 mm.
• the isomer indicated by the triplet, 3-(4-dimethylaminonaphthyl)-1,3,5-cycloheptatriene is isolated by stirring 2.6 g. (0.010 mole) of the mixture in 50 ml. of ethanol for 5 min. with 3 ml. of 40% aqueous tertafluoroboric acid, removing the solvent, and recrystallizing the solid from ethanol, M.P. 197199 C.
• the amine is liberated with aqueous sodium bicarbonate and extracted into ether to give 0.6 g. of product.
• the ultraviolet spectrum of this isomer has A max. 323 mu (log E 4.03).
• compositions are then separately coated at a wet thickness of 0.004 inch on an aluminum surface maintained at 100 F. to provide the coatings described in Tables 1, 2 and 3 below.
• the surface of each of the photoconductive layers so prepared is charged negatively to a potential of about 600 volts under a corona charger.
• the charged layer is covered with at transparent sheet bearing a pattern of opaque and lighttransmitting areas and exposed to the radiation from a 60 watt incandescent lamp at a distance of 100 cm. which provides an illumination intensity of about meter candles.
• the resultant latent image is developed by cascading over the surface of the layer a mixture of positively charged thermoplastic toner particles and glass beads, and the print fixed by heating. A reproduction of the original pattern results.
• the polymeric binder used in the coating compositions is a polyester of terephthalic acid and a mixture of ethylene glycol (1 part by weight)v and 2,2-bis(4-hydroxyethoxyphenyl)propane (9 parts by Weight).
• the sensitizers referred to in the tables are as follows:
• EXAMPLE 14 The procedure of Example 12 is repeated except that the relative speeds of the photoconductive layers are determined for both negative and positive charging. The results are set forth in Table 3.
• a photoconductive element is prepared in the manner set forth in Example 12 except that the photoconductor used is 3-(4-dimethylaminopheny1)-1,3,5-cycloheptatriene.
• the sample is charged under a positive corona and then exposed through a step tablet (0.15 density increments) for 12 seconds at a distance of 13 inches from a BOO-watt incandescent lamp.
• the exposed strips are then toned by conventional cascade development with a negatively charged thermoplastic toner.
• the toner image is fixed at 300-3S0 for one minute forming a-permanent image.
• the number of steps developed by this procedure is a measure of the photosensitivity of the system. Sixteen steps are developed using the above photoconductor. This procedure is repeated with various photoconductors. The number of steps developed is set forth in Table 4.
• An electrophotographic element comprising an electrically conducting support having coated thereon a photoconductive composition comprising a polymeric filmforming binder and a photoconducting amount of a photoconductor having a structure selected from the group consisting of:
• a sensitizer selected from the group consisting of a pyrylium salt, a thiapyrylium salt, a selenapyrylium salt, a fluorene, a carboxylic acid and a triphenyl methane dye.
• An electrophotographic element comprising an electrically conducting support having coated thereon a phoconductive composition comprising a polymeric binder and a photoconducting amount of a photoconductor selected from the group consisting of (4-dimethylaminophenyl) -1, 3 ,5 -cycloheptatriene,
• a sensitizer selected from the group consisting of a pyrylium salt, a thiapyrylium salt, a selenapyrylium salt, a fluorene, a carboxylic acid and a triphenyl methane dye.
• a photoconductive element for use in electrophotography comprising an electrically conducting support having coated thereon a photoconductive composition comprising:
• a photoconductive element for use in electrophotography comprising an electrically conducting support having coated thereon, a photoconductive composition comprising:
• a photoconductive element for use in electrophotography comprising an electrically conducting support having coated thereon a photoconductive composition comprising:
• a photoconductive element for use in electrophotography comprising an electrically conducting support having coated thereon a photoconductive composition comprising:
• a photoconductive element for use in electrophotography comprising an electrically conducting support having coated thereon a photoconductive composition comprising:

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• 1967
  • 1967-07-18 US US654091A patent/US3533786A/en not_active Expired - Lifetime
  • 1967-07-18 US US654092A patent/US3503740A/en not_active Expired - Lifetime
  • 1967-12-28 BE BE708638D patent/BE708638A/xx unknown
  • 1967-12-29 FR FR1583188D patent/FR1583188A/fr not_active Expired

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