Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B11/00—Diaryl- or thriarylmethane dyes
  • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
  • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
  • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
• • 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, 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 is alkyl of l to about 5 carbon atoms; and X is an anion residue.
• Such polymeric materials are highly effective sensitizers for organic photoconductors such as the poly(- vinylcarbazoles).
• the light struck are as' 'of th 'e irr'iag'ing l ayer'a're thus rendered conductive and tl'ie elecftr osta'tic chargeselectively dissipated in these irradiated zii'teasfAftet the photoconductor .is exposed, the latentH-electrostatic image on this image bearing Surface isrenderedvisible by development-with a finely divided .coloredelectroscopic material,.known in the,art as-tonerl? This toner will be principally attracted to. those areas-onlheimage bearing surface which retain. the/electrostatiocharge and thusrforma visiblespowder imagery-U t.
• the developed image can then be readorpermanently affixed tojthe ph'otoeonductof where the muging layer pot to be reu seld.
• This latterptactice is usually followedwith respectgto the: binder-typephotoconductive films: ejg'. Zinc oxide/insulating"resifi)'where the photoconductiveirnagirig layer i's'also'ari integral part of the'fi nishe d copy. l
• any one of a variety 'of well known techniques canbeused to'pernianent]y affix the toner image to the copy' she'et, "including ojvercoating with transparent fi mga a solvent oflthermal fusion of the toner particles to thELirm r't iv 'snb'tr'atelf
• thelrhaterials used in the photoconduct or layef siioiild pfefereably be capable ofrapid switching-from insulative" to conductive to insulativ'e-state-inforder to'permit cyclic use of the imaging layer.
• Typical ofthe materials suitable for'useifi sucha rapidlycycling-imagi ng system include anthracerfe; sul fur, selenium iHIlClM mlXtUfeS, thereof ('U.S Pat.il Joi 2,297,691 )iselenium being prefrr ed because of its superior photosensitivityfi. i i
• any one of a'number of organic photocdnductive materials can bep'resent' in the reaction mixture during the synthesis of this'polynieric dyestuff.
• Typical'of such organic photoconductive materials incliide 'any cf the polyvinylcar'bazoles "(e.”g.' poly(N- The dyestuff precursor compounds, namely the N- I alkyl- 3 -formyl carbazoles, which can be used in this process can betreadily prepared from commercially available materials by methods disclosed in the technical literature.
• niaterials which are suitablein this regard include N-methyl-3-formyl carbazol e, N-ethyl-3-formyl carbazole, ,N-propyl-3-formyl .carbazole, N-butyl-3-forr nyl carbazole and N-pentyl-3- fo rmyl carbazole.
• concentration of precursor compound(s) used in such synthesis is based upon the relative concentration. of acid and organic polymeric pho toconductive materialspresent in the reaction mixture.
• concentratiqniQf precursor inlthereaction mixture is in the range of from about ⁇ to about 50 parts by weight precursor pe rI lOQ partslby weight organic polymeric pho .toconduCtivc materials.
• the third essential component'of the reaction mass is an organic polymeric photoconductive material.
• organic polymeric photoconductive material and the dyestuff are, however; physically bound togetherf :during the condensation-polymerization of the precursor compound, thus,'forming a complex wherein the photoconductive ,material and the sensitize r arle intimately associated with one another.
• reaction mass thus-produced is agitated. and heated.
• the product will predominantly comprise a triaryl methane dye (nonpolymerized) having the following structural formula:
• a series of dyestuff senistized photoconductivecomthe reaction is quenched by pouring the reaction mass 55 positions are prepared from poly(N-vinylcarbazole) into a large volume of distilled water.
• the colored polymeric products precipitate out and are separated from the aqueous medium by filtration. Subsequent to removal of these aqueous residues the colored polymeric product is purified by reprecipitation from alternate solutions of water and methanol.
• the colored polymeric products After the colored polymeric products have been cleansed of impurities, it can be dissolved in a suitable solvent, such as chloroform or methylene chloride, and coated on a suitable conductive substrate (aluminized mylar, conductive glass plates, aluminum, etc.).
• a suitable conductive substrate aluminized mylar, conductive glass plates, aluminum, etc.
• the quantity, ,Ofmaterial which is imparted to such a substrate should be sufficient to form a photoconductive imaging film having a dry film thickness in the range of from about 0.5 to about 50 microns. It has been observed,.thatprior to casting of and N-ethyl-3-formyl carbazole. The exact proportion of these materials in each of the compositions is disclosed in Table I appearing immediately after the text of this Example.
• the poly(N- 6O vinylcarbazole) is initially dispersed in 50 grams polyphosphoric acid. N-ethyl-3-formyl carbazole is then added to'the dispersion while the dispersion is continuously vigorously agitated. The temperature of this dispersion is gradually increased to about 60C and there- 5 after maintained at this level for the prescribed reac- -vacuum and thereafter dissolved in a suitable solvent (e.g. chloroform or methylene chloride).
• a suitable solvent e.g. chloroform or methylene chloride.
• the casting solvent containing the polymeric composition is subjected to preillumination with activating electromagnetic radiation whereby its opticaldensity is substantially enhanced.
• the solution containing the colored polymeric solids is cast or coated on an appropriate conductive substrate.
• the quantity of colored polymeric materials that is transferred to such substrates is sufficient to form a substantially uniform film having a thickness in the previously prescribed range.
• Any' of the conductive substrates traditionally used in the preparation of el'ectrophotographic imaging members are suitable.
• EXAMPLE VI About 0.2 grams of the colored polymeric composition of Example I is dissolved in 6 milliliters of methylene chloride and thereafter coated on a conductive paper substrate such that its dry film thickness is about 15 microns. Subsequent to curing of this polymer coating, the resulting imaging mernber is processed in a standard electrophoto'grap'hic imaging system.
• source of illumination used in projecting the image pattern on the corona sensitized polymeric coating is a tungsten lamp.
• the amount of exposure required to give what was deemed to be an image of good quality is 70 lux. seconds.
• EXAMPLE VII pursues n1pad EXAMPLEVII
• the procedures of Example VI are repeated with the colored polymeric composition of Example Ill.
• the amount of exposure required to obtain an image comparable to that of Example I is 53 lux. seconds.
• the action spectrum for the material used in preparation of the imaging layer ofthe imaging member used in this Example is shown in FIG. 1. r
• EXAMPLE Vlll About 2 grams of the colored polymeric composition of Example lVis dissolved in about 1 milliliter of methylene chloride and the resulting solution subsequently irradiated from adistance of 30 centimeters with a fluorescent lamp (20 watts). The effects of such irradiation on a sample not having received such irradiation and samples irradiated for five minutes and 20 minutes respectively are shown in Table II.
• EXAMPLEQIX A About'O.l grams of the polymeric composition of Example IV and about 0.1 grams of poly(N- vinylcarbazole) are dissolved in 6 milliliters of methylene chloride. The resulting solution is subjected to irradiation in a manner similar to that of Example IX. Following irradiation, a conductive paper substrate is coated with said solutionr'Sufficient polymeric materials are transferred to the paper to provide a photoconductive imaging layer having a dryfilm thickness equal to about 15 microns. A comparative evaluation of the sensitivity of an irradiated sample with a non-irradiated sample are shown in Table III.
• organic polymeric photoconductive material is poly(vinylpryene).
• meric photoconductive material is poly(vinylpyrenal).
• heating of the mixture proceeds for an interval sufficient to produce a composition wherein the predominent component is about 50 parts by weight of a compound of the triaryl methane dyestuff of the formula above formula per 100 parts organic polymeric photoconductive material, and (iii) a quantity of polyphosphoric acid equivalent to about 5 to about times the weight of organic polymeric photoconductive material in the mixture; and

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Photoreceptors In Electrophotography (AREA)

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Cited By (3)

Citations (1)

• 1973
  • 1973-06-07 NL NL7307979A patent/NL7307979A/xx unknown
  • 1973-11-14 US US415594A patent/US3895945A/en not_active Expired - Lifetime

Patent Citations (1)

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