US3556786A - Dye sensitization of electrophotographic material - Google Patents

Dye sensitization of electrophotographic material Download PDF

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Publication number
US3556786A
US3556786A US639905A US3556786DA US3556786A US 3556786 A US3556786 A US 3556786A US 639905 A US639905 A US 639905A US 3556786D A US3556786D A US 3556786DA US 3556786 A US3556786 A US 3556786A
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United States
Prior art keywords
photoconductive
dye
zinc oxide
dyes
region
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US639905A
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English (en)
Inventor
Karel Eugeen
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Agfa Gevaert NV
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Agfa Gevaert NV
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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
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0585—Cellulose and derivatives
    • 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
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0542—Polyvinylalcohol, polyallylalcohol; Derivatives thereof, e.g. polyvinylesters, polyvinylethers, polyvinylamines
    • 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
    • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen

Definitions

  • This invention relates to photoconductive materials, and more particularly to photoconductive materials or compositions containing a dye that mainly absorbs in the read and near-infrared region of the spectrum.
  • Electrophotographic materials consisting of a support, on which a photoconductive substance is coated together with a binder are generally known in this respect.
  • photoconductive substances in such coatings specific inorganic as well as organic substances can be used, e.g. sulphur, selenium and compounds belonging to the type of the oxides, sulphides and selenides of zinc, cadmium, mercury, antimony, bismuth,titanium and lead, anthracene, anthraquinone, and a many recently discovered organic monomeric and polymeric photoconductors.
  • photoconductive zinc oxide has been selected for its high inherent sensitivity and brilliant white colour.
  • Zinc oxide constitutes an excellent contrasting base for developer materials applied thereto.
  • photoconductive zinc oxide Since photoconductive zinc oxide has little or no absorption power for light of the visible spectrum, it has sitivity and increase the total sensitivity of this zinc "oxide with dyes absorbing light in one or more ranges of the visible spectrum.
  • at least one complementary dye absorbing beyond 600 nm. more preferably in the region around 700 nm.
  • Dyes absorbing in that region are already known, e.g. pentamethine and hepta methine dyes such as those described in the Unitedf States patent specification 3,002,835 of Joze Kostelec, issued Oct. 10, 1961.
  • These dyes being in general not veryflstable to light, are less suited for a permanent sensitisat ion of the photoconductive substance or masking of the colouration of the sensitising dye, mainly absorbing in the region of 530 to 550 nm.
  • quinone-imine dyes absorbing in the region of the visible spectrum above 600 nm., are very suited to accomplish the requirements set forth above and moreover are substantially stable to light.
  • quinone-imine dyes indoaniline dyes are particularly useful, more particularly those represented by the following general formula:
  • R represents hydrogen or a substituent, more particularly of the type known in quinone-imine dye chemistry e.g. a substituent present in the structure of a colour coupler for cyan used in silver halide colour photography, e.g. a N alkyl substituted carbamyl group, a N-aryl-substit uted carbamyl group or a sulpho- R represents a p-dialkyl-aininophenyl group including a substituted p-dialkylaminophenyl group, e.g.
  • N tR2 represents-the residue of acoupled aromatic primary amino colour developer used in silver halide colour "photography, and e Z represents the necessary atoms to close an aromatic: ring" system, including a substitutedring syste-m,e.g'. t the benzene series and naphthalene series, but-preferably of'the naphthalene series v
  • a substitutedring syste-m e.g'. t the benzene series and naphthalene series, but-preferably of'the naphthalene series v
  • colour couplers suited for the production ofquinone-imine dyes referenceis made,;e.g., to lafkides Photographic Chemistry-Vol. II (1960) Fountain Press.London, pp. 53 6-537 and the United Kingdom patent specifications 831,731 filed June 20, 1957, 939,030 filed Oct.
  • This mixture was ground in a sand-mill whereupon 391 g. of a 20% solution of copoly( viny1 acetate/vinyl laurate) (80/20) in ethylene chloride were added together with a mixture of 65 g. of ethanol, 212 g. of ethylene dichloride and 31 g. of a 10% solution of monobutyl phosphate in ethanol. To the obtained mixture 90 ccs. of a 0.1% solution of one of the dyes, listed in Table I, in ethanol were added.
  • compositions were coated on a glassine paper support weighing 65 g./sq. m., pro rata of 19 g. of zinc oxide per sq. m.
  • the materials were then negatively charged with a corona, the potential difference between the wires and the ground being -6,000 v.
  • the charged materials were exposed through a step wedge with a constant 0.1 by means of an incandescent lamp of 450 watt with a radiation intensity of 2,280 lux.
  • the quinoneimine dyes are preferably used as complementary dyes in combination with spectral sensitisers for the range 480 to 5 nm.
  • binding agent for the photoconductive zinc oxide any suitable resin may be employed as binding agent for the photoconductive zinc oxide, reference is particularly made to those described in the Belgian patent specification 612,102 filed Dec. 29, 1961 by Gevaert Photo-Producten N.V.
  • the said binding agents are soluble in an organic solvent and are usually applied as an organic solution containing the photoconductive zinc oxide dispersed therein.
  • a particularly suitable binding agent composition for application from an organic solvent or mixture of solvents is a mixture of ethylcellulose and a copoly(vinyl acetate/vinyl laurate) (80/20). In this mixture preferably up to 30% by weight of ethylcellulose is provided.
  • Suitable resin compositions which can be applied from a solution in water, are those described in our published Dutch patent applications 6608815, 6608814 and 6608816, all of them filed June 24, 1966.
  • the ratio of photoconductor with respect to binder is preferably comprised between 50 and by volume.
  • acid substances and salts thereof described in the Belgian patent specification 6l2,102 filed Dec. 29, 1961 by Gevaert Photo- Producten N.V.
  • the photoconductive coating composition containing the quinino-imine dyestuif can be coated on a support by a known coating technique, e.g. by spraying, whirling, dip-coating, or by a coating technique wherein use is made of a doctor blade.
  • a known coating technique e.g. by spraying, whirling, dip-coating, or by a coating technique wherein use is made of a doctor blade.
  • the supports or base materials are chosen in view of the particular charging, exposing, recording, developing and/ or transfer technique wherein the recording material has to be used.
  • the support preferably possesses an electric volume resistivity that is considerably lower than that of the recording layer.
  • Suitable supports are described, e.g. in the United Kingdom patent specifications 995,491 filed Mar. 16, 1962, 1,020,503 filed Nov. 8, 1961 and 1,020,504 filed Dec. 29, 1961 all by Gevaert Photo-Producten N.V.
  • composition was intimately mixed in a sand-mill and then coated on a glassine paper support weighing 65 g./sq. m., pro rata of 19 g. of zinc oxide per sq. m.
  • the resulting material was negatively charged with a corona, the potential difference between the wires and the ground being 6,000 v.
  • the charged material was exposed through a step wedge with a constant 0.1 by means of an incandescent lamp of 450 watt with a radiation intensity of 2,280 lux. Subsequently, the material was developed electrophoretically.
  • the sensitivity of the obtained recording layer was expressed by the number of steps corresponding with the discharged areas wherein no developing powder was deposited, thus having the original density of the recording layer. The higher that number, the more sensitive is the layer. The number of non-blackened steps obtained in this example was 20.
  • the reflexion curve (percent reflexion versus wavelength in nanometer) of the material obtained is shown in FIG. 1.
  • composition was mixed and coated as described in Example 2.
  • Example 2 The resulting material was then further treated as described in Example 2.
  • the number of non-blackened steps obtained in this example was 24.
  • the reflection curve of the material obtained is shown in FIG. 2 (percent reflection versus wavelength in nanometer).
  • a photoconductive recording material containing a photoconductive recording layer comprising photoconductive zinc oxide in finely divided particle form dispersed in a binder, a spectrally sensitizing dye for said zinc oxide sensitizing in the region of about 530 to 550 nm., and a quinone-imine dye, which is represented by the following general formula:
  • R is hydrogen, or a substituent of the type known in quinone-imine dye chemistry and selected from the group consisting of a N-alkyl-substituted carbamyl group, a N-aryl-substituted carbamyl group or a sulphoaryl group,
  • R is a p-dialkyl-aminophenyl group
  • Z represents the necessary atoms to close an aromatic ring system, said quinone-imine dye increasing the spectral sensitivity of the recording layer in the region of about 600-700 nm.
  • a photoconductive recording material where in the spectrally sensitising dye, sensitising in the region of 530 to 550 nm., is Eriochrom Geranol-R (Cl. 43,865).
  • a photoconductive recording material wherein the spectrally sensitising dye, sensitising in the region of 530 to 550 nm. is Eriochrom-Cyanine-R (C.I. 43,820).

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Photoreceptors In Electrophotography (AREA)
US639905A 1966-05-20 1967-05-19 Dye sensitization of electrophotographic material Expired - Lifetime US3556786A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB22631/66A GB1142509A (en) 1966-05-20 1966-05-20 Improved electrophotographic material

Publications (1)

Publication Number Publication Date
US3556786A true US3556786A (en) 1971-01-19

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US639905A Expired - Lifetime US3556786A (en) 1966-05-20 1967-05-19 Dye sensitization of electrophotographic material

Country Status (5)

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US (1) US3556786A (ref)
BE (1) BE698750A (ref)
DE (1) DE1572327C3 (ref)
GB (1) GB1142509A (ref)
NL (1) NL154842B (ref)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3044693A1 (de) * 1980-11-27 1982-07-08 Helmut 7015 Korntal Hoffmann Verfahren zum aufbringen von isolierschichten
US5460930A (en) * 1993-10-28 1995-10-24 Eastman Kodak Company Photographic elements containing indoaniline dummy dyes

Also Published As

Publication number Publication date
BE698750A (ref) 1967-11-22
GB1142509A (en) 1969-02-12
NL154842B (nl) 1977-10-17
DE1572327B2 (de) 1974-12-12
DE1572327A1 (de) 1970-02-26
NL6706575A (ref) 1967-10-25
DE1572327C3 (de) 1975-08-14

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