US3448030A - Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes - Google Patents

Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes Download PDF

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Publication number
US3448030A
US3448030A US467345A US46734565A US3448030A US 3448030 A US3448030 A US 3448030A US 467345 A US467345 A US 467345A US 46734565 A US46734565 A US 46734565A US 3448030 A US3448030 A US 3448030A
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United States
Prior art keywords
image
pigment
plate
color
light
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Expired - Lifetime
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US467345A
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English (en)
Inventor
Lester Weinberger
Basil M Kyriakakis
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Xerox Corp
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Xerox Corp
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Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Priority to US467345A priority Critical patent/US3448030A/en
Priority to CA963,998A priority patent/CA943801A/en
Priority to GB28660/66A priority patent/GB1155554A/en
Application granted granted Critical
Publication of US3448030A publication Critical patent/US3448030A/en
Priority to BE743893D priority patent/BE743893A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/2409—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62
    • C09B5/2418—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62 only oxygen-containing hetero rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
    • G03G17/04—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process using photoelectrophoresis
    • 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
    • G03G5/0624—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

Definitions

  • the condensing agent added to the solution may be any suitable strong base. Triethylamine is preferred since it results in high yields. Other typical strong bases include piperidine, pyridine, dimethyl aniline, tripropylamine, etc.
  • Example II About one mole of 2,3-dichloro-1,4-naphthoquinone is mixed with about 0.9 mole 2-hydroxy-3-anthroyl-2'-methylanilide in about 500 ml. isopropanol. The solution is heated to its boiling point, at which time about 2.5 mole tn'ethylamine is added. Reflux is continued for about one half hour. The mixture is then cooled to room temperature, filtered, washed with warm acetone and dried under vacuum. A portion of the resulting magenta crystals is then washed with quinoline and dried. The product is anthra-[2,1,;3]-naphtho-[2,3-d] furan 9,14- dione-7-(2'-methylphenyl) carboxamide.
  • compositions within the general formula listed above, and mixtures thereof, are especially useful as photo-sensitive pigment particles in electrophoretic imaging processes.
  • An exemplary electrophoretic imaging system is shown in the figure.
  • particles of a single color are dispersed in the carrier liquid and exposed to a blaJck-and-white image.
  • a single color image results, corresponding to conventional black-'aud-white photography.
  • the particles are selected so that those of different colors respond to dif- -ferent wavelengths in the visible spectrum corresponding to their principal absorption bands.
  • the pigments should be selected so that their spectral response curves do not have substantial overlap, thus allowing for good color separation and subtractive multicolor image formation.
  • the particle dispersion should include cyan colored particles sensitive mainly to red light, magenta colored particles sensitive mainly to green light, and yellow colored particles sensitive mainly to blue light.
  • the photosensitive pigment resin photoconductive layer may be used in the formation of multilayer sandwich configurations adjacent a dielectric layer, similar to that shown by Golovin et al., in the publication entitled, A New Electrophotographic Process, Effected by Means at Combined Electret Layers, Doklady Akad. Nauk SSSR vol. 129, No. 5, pp. 1008- 1011, November-December, 1959.
  • the pigments may be incorporated in the dissolved or melted binder resin by any suitable means such as strong sheer agitation, preferably with simultaneous grinding. These include ball milling, roller milling, sand milling, ultrasonic agitation, high-speed blending and any desirable combination of these methods. Any suitable range of pigment-resin ratios maybe used.
  • any suitable material may be used as the surface deformable coating over the photoconductive layer or as the binder for the photosensitive pigments in a self-deformable layer.
  • Typical surface deformable thermoplastic polymers are low molecular weight polymers or oligomers. Any suitable polymer may be used in the surface deformation process of this invention; typical polymers are aromatic polymers such as polystyrene, alpha methylstyrene; copolymers made from styrene and other materials such as vinyl toluene, methyl-styrene, polyalphamethyl styrene, chlorinated styrene, and polymers and copolymers made from petroleum cuts and indene polymers; phenolics such as phenol aldehyde resins, phenol formaldehyde resins and mixtures thereof; vinyl polymers such as polyvinylacetate, polyvinylalcohol, polyvinylbutyral, butylmethyl acrylate styrene polymers,
  • a process for forming a latent xerographic image on a photoconductive layer comprising a photoconductive pigment in an organic binder, which comprises electrostatically charging said layer and exposing said layer to a pattern of activating electromagnetic radiation, said photoconductive pigment comprising the composition having the general formula:
  • a method for forming an image on a surface deformable recording medium which comprises electrostatically charging the recording medium of claim 7, exposing said medium to a pattern of light and shadow and maintaining the surface of said medium in a sufliciently viscous condition to thereby deform at least a portion of said surface in a configuration corresponding to said pattern of light and shadow.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Molecular Biology (AREA)
  • Photoreceptors In Electrophotography (AREA)
US467345A 1965-06-28 1965-06-28 Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes Expired - Lifetime US3448030A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US467345A US3448030A (en) 1965-06-28 1965-06-28 Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes
CA963,998A CA943801A (en) 1965-06-28 1966-06-27 Electrically photosensitive particles useful in electrophotographic imaging processes
GB28660/66A GB1155554A (en) 1965-06-28 1966-06-27 Electrophotographic Processes
BE743893D BE743893A (cs) 1965-06-28 1969-12-30

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US467345A US3448030A (en) 1965-06-28 1965-06-28 Electrically photosensitive particles useful in photoelectrophoretic and xerographic imaging processes

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US3448030A true US3448030A (en) 1969-06-03

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US (1) US3448030A (cs)
BE (1) BE743893A (cs)
CA (1) CA943801A (cs)
GB (1) GB1155554A (cs)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527684A (en) * 1967-03-13 1970-09-08 Eastman Kodak Co Method of increasing contrast in electrophoretic reproduction
US4012252A (en) * 1973-10-29 1977-03-15 Xerox Corporation Imaging process utilizing 3-bromo-N-2"-pyridyl-8,13-dioxodinaphtho-(2,1-b;2',3'-d)-furan-6-carboxamide
US4259425A (en) * 1979-05-11 1981-03-31 Monsanto Company Electrographic recording material
US5376784A (en) * 1993-06-17 1994-12-27 Weinberger; Lester Hybrid organic-inorganic bistable nonlinear optical device
US5543631A (en) * 1993-06-17 1996-08-06 Weinberger; Lester Hybrid organic-inorganic bistable nonlinear optical gate
FR2806408A1 (fr) * 2000-03-17 2001-09-21 Oreal Composition cosmetique comprenant un derive de furane- naphtoquinone, leur utilisation comme agent colorant et derives

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2893998A (en) * 1958-05-20 1959-07-07 Du Pont Anthraquinone vat dyes
US2976287A (en) * 1958-12-03 1961-03-21 Gen Aniline & Film Corp Naphthofuranedione vat dyestuffs
US3147283A (en) * 1961-08-10 1964-09-01 Ciba Ltd New dyestuffs of the naphthofurandione series
US3238041A (en) * 1962-05-08 1966-03-01 Xerox Co Relief imaging of photoresponsive member and product
US3244516A (en) * 1959-04-09 1966-04-05 Azoplate Corp Electrophotographic mateiral and process

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2893998A (en) * 1958-05-20 1959-07-07 Du Pont Anthraquinone vat dyes
US2976287A (en) * 1958-12-03 1961-03-21 Gen Aniline & Film Corp Naphthofuranedione vat dyestuffs
US3244516A (en) * 1959-04-09 1966-04-05 Azoplate Corp Electrophotographic mateiral and process
US3147283A (en) * 1961-08-10 1964-09-01 Ciba Ltd New dyestuffs of the naphthofurandione series
US3238041A (en) * 1962-05-08 1966-03-01 Xerox Co Relief imaging of photoresponsive member and product

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527684A (en) * 1967-03-13 1970-09-08 Eastman Kodak Co Method of increasing contrast in electrophoretic reproduction
US4012252A (en) * 1973-10-29 1977-03-15 Xerox Corporation Imaging process utilizing 3-bromo-N-2"-pyridyl-8,13-dioxodinaphtho-(2,1-b;2',3'-d)-furan-6-carboxamide
US4259425A (en) * 1979-05-11 1981-03-31 Monsanto Company Electrographic recording material
US5376784A (en) * 1993-06-17 1994-12-27 Weinberger; Lester Hybrid organic-inorganic bistable nonlinear optical device
US5543631A (en) * 1993-06-17 1996-08-06 Weinberger; Lester Hybrid organic-inorganic bistable nonlinear optical gate
FR2806408A1 (fr) * 2000-03-17 2001-09-21 Oreal Composition cosmetique comprenant un derive de furane- naphtoquinone, leur utilisation comme agent colorant et derives
EP1134217A3 (fr) * 2000-03-17 2001-11-28 L'oreal Composition cosmétique comprenant un dérivé de furane-naphtoquinone, leur utilisation comme agent colorant, et dérivés.

Also Published As

Publication number Publication date
BE743893A (cs) 1970-06-30
CA943801A (en) 1974-03-19
GB1155554A (en) 1969-06-18

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