US3811883A - Photoelectrophoretic imaging process employing napthofuranediones - Google Patents

Photoelectrophoretic imaging process employing napthofuranediones Download PDF

Info

Publication number
US3811883A
US3811883A US00207179A US20717971A US3811883A US 3811883 A US3811883 A US 3811883A US 00207179 A US00207179 A US 00207179A US 20717971 A US20717971 A US 20717971A US 3811883 A US3811883 A US 3811883A
Authority
US
United States
Prior art keywords
particles
colour
electrode
light
image
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00207179A
Other languages
English (en)
Inventor
G Zographos
C Frey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Application granted granted Critical
Publication of US3811883A publication Critical patent/US3811883A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • 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

Definitions

  • R denotes an arylene radical
  • X and Y denote hydrogen or halogen atoms or alkyl or alkoxy groups
  • X and Y together with two adjacent C atoms of the 'base substance can form a benzene ring, or
  • An essential component of the system are the suspended particles which must be electricallyphotosensitive. These particles evidently undergo a change in charge during irradiation with an activating electromagnet radiation, and in particulardo so through interaction with one of the electrodes.
  • particles of a single colour are used, whereby a single-colourimage is produced which is equivalent to a customary black and white image.
  • the images are produced in a natural colour, since mixtures of particles of two or more different colours eachsensitive to light of a specific wavelength or of a narrow wavelengthrange, are used.
  • the 4,4-diaminodianthraquinonyl is known amongst the series of the naphthofuranediones, the dyestuffs of the formula wher ein X and Y denote chlorine atoms or alkyl 5 groups, or the dyestuff of the formula CONH may especially ,be mentioned. These dyestuffs are known. Their manufacture is described in German Pat. No. 1,209,683.
  • the dyestuffs are preferably in a finely divided form, the average particle size appropriately being less than 10 n and advantageously between 0.1 and 5 11.. It is advantageous if the particles are of uniform size.
  • the toners appropriately contain a binder which permits the pigment particles to be fixed to the final image carrier.
  • the specific resistance of the binder should be greater than Ohm.cm, and appropriately greater than 10 Ohm.cm.
  • Natural, semi-synthetic or synthetic resins such as abietic acid esters, tetrahydroabietic acid esters, cellulose esters, cellulose ethers, chlorinated rubber, vinyl resins, such as, for example, polyvinyl chloride, polyvinyl acetate, copolymers of vinyl chloride and vinyl acetate, polyvinyl acetals, polyvinyl alcohols, polyvinyl ethers, polyvinylcarbazole, polyisobutylene, polybutadiene, polyacrylic esters or polymethacrylic esters, polystyrene, polyacrylonitrile or silicone resins are suitable for this purpose.
  • the proportion of binder in the toner is appropriately between 10 and 60 percent. It proves to be advantageous to achieve as intimate a mixing of the toner with the binder as possible, for example, on grinding or kneading the two materials together. In doing so, the desired reduction in particle size can be achieved simultaneously if a crude pigment is employed.
  • the drawing shows a transparent electrode 1 which in this case consists of a layer of an optically transparent glass 2 which is coated with a thin optically transparent layer 3 of tin oxide.
  • This material is commercially available under the description. NESA-glass.”
  • This electrode is subsequently described as the injector electrode.”
  • a thin layer 4 of finely divided, lightsensitive particles, dispersed in an insulating liquid carrier, is coated onto the surface of the injector electrode 1.
  • the term light-sensitive is to be understood, according to the invention, as indicating the property of a particle that, once it has been attracted by the injector electrode, it migrates away from the electrode under the influence of an applied electrical field if an irradiation with an actinic electromagnetic radiation is carried out.
  • the liquid suspension 4 can furthermore contain a sensitising agent and/or a binder for the pigment particles, these agents being at least partially soluble in the suspending liquid or carrier liquid, as will still be described in more detail below.
  • a projector consisting of a light source 8, a diapositive 9 and a lens 10 irradiates the dispersion 4 with a light image of the diapositive 9 which is to be reproduced.
  • the electrode 5 is constructed in the form of a roller with a conducting central core 11 connected to the potential source 6.
  • the core is covered with a layer of a blocking electrode material 12, which can be baryte paper.
  • the pigment suspension is irradiated with the image to be reproduced, whilst applying a potential at right angles to the blocking electrode and injector electrode by closing the switch 7.
  • the roller 5 is rolled over the upper surface of the injector electrode 1 during the image irradiation, whilst the switch 7 is closed.
  • the irradiation withlig ht is that exposed pigment particles, which have originally been attracted by the electrode I, migrate through the liquid and adhere to the surfaces of the blocking electrode, leaving, on the injector electrode surface, a pigment image which is a duplicate of the diapositive 9.
  • the relatively volatile carrier liquid evaporates, leaving the pigment image.
  • This pigment image can subsequently be fixed in situ, for example by applying a coating layer to the upper surface, or by means of a binder, such as, for example, paraffin wax, dissolved in the carrier liquid.
  • a binder such as, for example, paraffin wax
  • Other suitable binders which are obtainedfroiii the solution when the carrier liquid evaporates can also be used. About 3 6 per cent .by weight of the paraffin binder in the carrier give good results.
  • the carrier liquid itself can be a liquid paraffin wax or some other suitable binder.
  • the pigment image which is left on the injector electrode can be transferred to another surface and fixed thereon.
  • this system can produce either monochromatic or polychromatic images, depending on the type and number of the pigments which are suspended in the carrier liquid and depending on the colour of the light with which this suspension is irradiated when carrying out the process.
  • any suitable insulating liquid can be used as a carrier for the pigment particles in this system.
  • Typical carrier liquids are decane, dodecane, N-tetradecane, paraffin, wax or other thermoplastic materials, Sohio Odorless Solvent 3440 (a kerosene fraction marketed by Standard Oil Company, Ohio) and lsopar-E (a branched saturated aliphatic hydrocarbon marketed by Esso Oil Company, New Jersey). Images of good qualityare obtained at voltages of between 300 and 5,000 volt, which are applied when using the device described in the attached drawing. The proportion of pigment in the solvent is appropriately 2 10 percent. The addition of smaller amounts, for example 0.5 5 mol percent, of electron donors or'electron acceptors to the suspensions results in a marked improvement of the light sensitivity of the system.
  • a monochromatic system particles of the same composition are dispersed in the carrier liquid and irradiated with a black and white image. Thereby, a single colour is obtained, analogous to a customary black and white image.
  • the particles are so chosen that the particles with different colours respond to the various wavelengths in the visible spectrum, in accordance with their main absorption bands.
  • the pigments should be so chosen that their spectral response curves do not significantly overlap, so that a colour separation and a subtractive multi-colour image production is possible.
  • the dispersion of particles should contain particles of cyan colour, which are mainly sensitive to'red light, particles of magenta colour, which are mainly sensitive to green light, and particles of yellow colour, which are mainly sensitive to blue light.
  • these particles produce a liq uid of black appearance. If one or more of these particles migrate from the electrode 11 in the direction of the upper'electrode, particles are left which produce a colour which is equivalent to the colour of the incident light.
  • the result of an irradiation with red light is that the pigments of cyan colour migrate, leaving the pigments of magenta colour and the pigments of yellow colour.
  • the combination of these colours gives a final red image.
  • blue and green colours are reproducedby removal of pigments of yelgood spectral response and their high light sensitivity result in the formation of dense and brilliant images.
  • the examples which follow are carried out in a device which corresponds to the type illustrated by the attached drawing.
  • the image production mixture 4 is applied to an NESA-glass substrate.
  • the irradiation takes place through this glass.
  • the NESA-glass surface is wired in series with a switch, a potential source and the conducting core of a roller which has a baryte paper covering on its surface.
  • the roller has a diameter of about 63 mm (2% inches) and is moved over the surface of the plate at a speed of about 1.45 cm per second.
  • the plate used is about 19.3 cm (3 square inches) in size and is irradiated with a light intensity of 8,000 foot candles, measured on the uncoated NESA-glass surface.
  • the magnitude of the potential applied is 2,500 volt.
  • the irradiation is carried out with a 3,200 K lamp through a neutral dense wedge filter to measure the sensitivity of the suspensions to white light, and through Wratten filters 29, 61 and 47b, each placed by themselves in front of the light source, in order to measure the sensitivity of the suspensions to red, green and blue light, respectively, in separate tests.
  • the dyestuffs according to the invention are also suitable for other photoelectrophoretic reproduction processes.
  • EXAMPLE 1 10g of 4,4'-'diamino-l,l'-dianthraquinonyl of average particle size maximally l u are suspended in g of lsopar E, a saturated aliphatic hydrocarbon obtainable from ESSO Standard. The resulting paste is employed, either as such or diluted with further lsopar E, for the process described above. Brilliant, red images of excellent transparency and fastness to light are obtained.
  • EXAMPLE 2 The procedure in Example 1 is followed, but the dyestuffs of the formula particles of at least one colordispersed in an electrically insulating liquid carrier, said particles comprising a photosensitive pigment selected from the group consisting of naphthofuranediones of the formula cami 'nmaea" p wherein R denotes an arylene radical,
  • N H I -1 (H) CONH- are used as toners, thus yielding brilliant yellow images- C ONE- K/K I is used as photosensitive pigment.

Landscapes

  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US00207179A 1970-12-16 1971-12-13 Photoelectrophoretic imaging process employing napthofuranediones Expired - Lifetime US3811883A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1861670A CH558209A (de) 1970-12-16 1970-12-16 Verwendung organischer pigmente bei der elektrophoretischen bilderzeugung.

Publications (1)

Publication Number Publication Date
US3811883A true US3811883A (en) 1974-05-21

Family

ID=4434187

Family Applications (1)

Application Number Title Priority Date Filing Date
US00207179A Expired - Lifetime US3811883A (en) 1970-12-16 1971-12-13 Photoelectrophoretic imaging process employing napthofuranediones

Country Status (5)

Country Link
US (1) US3811883A (enExample)
JP (1) JPS5427734B1 (enExample)
CH (1) CH558209A (enExample)
DE (1) DE2162296C3 (enExample)
GB (1) GB1357974A (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966466A (en) * 1974-12-17 1976-06-29 Xerox Corporation Photoelectrophoretic imaging process using dark charge injecting agent on blocking electrode
US4017311A (en) * 1974-07-29 1977-04-12 Xerox Corporation Photoelectrophoretic imaging suspension
US4104064A (en) * 1974-07-29 1978-08-01 Xerox Corporation Photoelectrophoretic imaging method employing dinaphtho-furan-dione pigments

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1115578A (en) * 1977-07-25 1982-01-05 Frank G. Webster Electrophotosensitive materials for migration imaging processes
US4165985A (en) * 1978-05-24 1979-08-28 Eastman Kodak Company Electrophotosensitive materials for migration imaging processes
JP2022045895A (ja) * 2020-09-09 2022-03-22 保土谷化学工業株式会社 黄色系化合物、該化合物を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3448028A (en) * 1964-12-28 1969-06-03 Xerox Corp N-substituted - 8,13-dioxodinaphtho (2,1-b; 2',3'-d)-furan - 6 - carboxamides as electrically photosensitive materials in electrophotographic processes
GB1316667A (en) * 1969-05-26 1973-05-09 Xerox Corp Benzobrazanquinone pigments
US3484029A (en) * 1968-11-12 1969-12-16 John E Gaydos Wire hanger clip

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4017311A (en) * 1974-07-29 1977-04-12 Xerox Corporation Photoelectrophoretic imaging suspension
US4104064A (en) * 1974-07-29 1978-08-01 Xerox Corporation Photoelectrophoretic imaging method employing dinaphtho-furan-dione pigments
US3966466A (en) * 1974-12-17 1976-06-29 Xerox Corporation Photoelectrophoretic imaging process using dark charge injecting agent on blocking electrode

Also Published As

Publication number Publication date
JPS5427734B1 (enExample) 1979-09-12
CH558209A (de) 1975-01-31
DE2162296C3 (de) 1982-02-11
DE2162296B2 (de) 1981-06-11
GB1357974A (en) 1974-06-26
DE2162296A1 (de) 1972-06-22

Similar Documents

Publication Publication Date Title
US3560360A (en) Photoelectrophoretic imaging process using anthraquinones as the electrically photosensitive particles
US3442781A (en) Photoelectrophoretic and xerographic imaging processes employing triphenodioxazines as the electrically photosensitive component
US3553093A (en) Color photoelectrophoretic imaging process
US3825422A (en) Imaging process
US3900318A (en) Use of sublimable disperse dyes in photoelectrophoretic image reproduction
US3976485A (en) Photoimmobilized electrophoretic recording process
US3485738A (en) Photoelectrophoretic imaging process employing a layer of insulating liquid to improve image quality
US3546085A (en) Photoelectrophoretic imaging process and suspension
US3615558A (en) Photoelectrophoretic imaging process employing a finely divided phthalocyanine pigment
US3669872A (en) Imaging system
US3811883A (en) Photoelectrophoretic imaging process employing napthofuranediones
US3635981A (en) Photoelectrophoretic imaging pigment composition and process
US3448029A (en) Electrophoretic imaging process using 8,13-dioxodinaphtho - (2,1 - b; 2',3'-d) - furan-6-carboxamide pigments
US3551313A (en) Image contrast control in photoelectrophoretic imaging
US3595771A (en) Method of removing accumulated charges in photoelectrophoretic imaging
US3681064A (en) Photoelectrophoretic imaging process employing multicomponent electrically photosensitive particles
US3658675A (en) Photoelectrophoretic imaging processes using bisazo pigments
US3574182A (en) Calcium salt of 6-bromo-1-(1'-sulfo-2'-naphthylazo)-2-naphthol
US3852064A (en) Use of dioxazine pigment in the photoelectrophoretic production of images
US3445227A (en) Electrophotographic imaging processes employing 2,4-diamino-triazines as the electrically photosensitive particles
US4179209A (en) Multicolor line screen
US3915702A (en) Photoelectric and electrophotographic pigments comprising derivatives of condensed polycyclic aromatic hydrocarbon aldehydes
US3562248A (en) Bisazo pigments derived from couplers obtained by condensing 8-amino-2-naphthols with dicarboxylic acid chlorides
US3485633A (en) Electrophoretic imaging process employing metallic lakes of fluorescein derivatives as the electrically photosensitive material
US3867141A (en) Photoelectric and electrophotographic pigments comprising derivatives of condensed polycyclic aromatic hydrocarbon aldehydes