WO1992005476A1 - Direction de charge fondee sur la solvatation de compositions de revelateur electrophotographique liquides - Google Patents

Direction de charge fondee sur la solvatation de compositions de revelateur electrophotographique liquides Download PDF

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Publication number
WO1992005476A1
WO1992005476A1 PCT/US1990/006837 US9006837W WO9205476A1 WO 1992005476 A1 WO1992005476 A1 WO 1992005476A1 US 9006837 W US9006837 W US 9006837W WO 9205476 A1 WO9205476 A1 WO 9205476A1
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Prior art keywords
toner
charge
solvation
charge director
resinous phase
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PCT/US1990/006837
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English (en)
Inventor
Ronald Swidler
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Commtech International Management Corporation
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Application filed by Commtech International Management Corporation filed Critical Commtech International Management Corporation
Priority to JP50320791A priority Critical patent/JP3238148B2/ja
Priority to CA002092707A priority patent/CA2092707C/fr
Priority to DE69033748T priority patent/DE69033748T2/de
Priority to AT91902923T priority patent/ATE202220T1/de
Priority to EP91902923A priority patent/EP0548076B1/fr
Publication of WO1992005476A1 publication Critical patent/WO1992005476A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/135—Developers with toner particles in liquid developer mixtures characterised by stabiliser or charge-controlling agents
    • G03G9/1355—Ionic, organic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/12—Developers with toner particles in liquid developer mixtures
    • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components

Definitions

  • the present invention relates generally to the field of color electrophotography, and more particularly relates to an improved method for charge directing liquid electrophotographic developer compositions, and to novel toner and developer compositions produced thereby.
  • a photoconductive insulating material such as selenium
  • a light image is then focused onto the charged surface, which discharges or lowers the potential of the irradiated areas, while leaving the remainder of the surface charged.
  • the electrostatic image so formed is then made visible by application of a suitable developing composition, which may be in either dry or liquid form.
  • a suitable developing composition which may be in either dry or liquid form.
  • Conventional liquid developer compositions comprise a dispersion of pigment particles in an insulating carrier liquid. Application of such a composition to the substrate carrying the electrostatic image results in migration of charged pigment particles to the substrate surface and deposition thereon in conformance with the electrostatic image.
  • Liquid developers for use in multicolor image development are relatively recent, and are comprised of colorant embedded in a thermoplastic resin core. These "toner” particles are then dispersed in an insulating carrier medium as above. Like compositions used in black-and-white electrophotography, these developer compositions additionally contain "charge directors”, or “charge control agents”, to control the charge acquired by the toner particles in the insulating liquid.
  • each of the color images is transferred from the electrophotographic member to a print substrate after development and prior to formation of the next color image. This process, however, requires extremely accurate registration of the successive color images on the substrate to which they are transferred in order to obtain a high-quality composite image.
  • Another color printing process, and the process currently in use commercially, is a four-color liquid electrophotographic process known as "consecutive color toning" or "consecutive multicolor image development".
  • This process involves: (l) charging a photoconductive ("pc") surface; (2) impressing a first latent image on the surface by exposure through a colored transparency; (3) developing the image by contacting the pc with a liquid developer composition of a first color, typically yellow; and (4) discharging the pc surface.
  • the steps are then repeated in sequence, typically using magenta, cyan, and black developer compositions, i.e., the cyclic process is repeated until the colored image is complete.
  • toner instability i.e., the appearance of toner in uncharged, non-image areas (a problem which is ubiquitous in zinc oxide and other positive toner systems) ; poor image resolution (i.e., poor edge acuity); poor image density resulting from insufficient deposition of toner particles in intended image regions; and "image" or "character” staining, where a second process color overtones the first image in regions where portions of the first image should have been discharged but were not.
  • An additional problem with current electrophotographic color development processes is the need for multiple washing and drying steps during development, e.g., as described by Alexandrovich et al. in U.S. Patent No. 4,701,387.
  • the method is somewhat time-consuming and unwieldy (it is recommended in the '387 patent that "after each development step and before the next developer is applied, the developed image is rinsed.... After rinsing, the rinse liquid is removed from the photoconductive element by drying, wiping or other method."; see column 2, lines 62-67).
  • the invention herein now provides a novel method for charge directing liquid electrophotographic developer compositions which addresses the aforementioned problems.
  • the invention is premised on the generation of an extremely stable charge director/toner complex, which in turn provides a very stable developer composition of exceptionally high particle-mediated conductivity and charge.
  • the present method and associated compositions provide for a streamlined development process and enable preparation of a final electrophotographic print of unex ⁇ pectedly high quality.
  • Electrophotographic processing generally: R.M. Schaffert, Electrophotography (London: Focal Press, 1975) , provides a comprehensive overview of electrophotographic processes and techniques.
  • Representative references which relate to the field of color electrophotography specifically, include U.S. Patent Nos. 3,060,021 to Greig, 3,253,913 to Smith et al., 3,285,837 to Neber, 3,337,340 to Matkan, 3,553,093 to Putnam et al., 3,672,887 to Matsumoto et al., 3,687,661 to Sato et al. , and 3,849,165 to Stahly et al.
  • References which describe electrophotographic toners and developers include U.S. Patent Nos.
  • References which relate to charge directors include U.S. Patent Nos. 3,012,969 to van der Minne et al. (polyvalent metal organic salts in combination with an oxygen-containing organic compound) , 3,411,936 to Rots an et al. (metallic soaps), 3,417,019 to Beyer (metallic soaps and organic surface active agents), 3,788,995 to Stahly et al. (various polymeric agents), 4,170,563 to Merrill et al. (phosphonates) ,
  • thermosetting binder resins such as polyisocyanate-cured alkyd resins, epoxy ester resins and copolymers of a vinyl monomer and styrene, acrylic and methacrylic esters or the like, alkyd resins cured with mela ine formaldehyde, or benzoguani ine formaldehyde, drying oil modified alkyd resins, and epoxy ester resins cured with a catalyst.
  • alkyd and modified alkyd resins e.g., soya oil-modified and linseed oil-modified alkyds
  • phenolic and modified phenolic resins phenol formaldehyde resins and derivatives thereof.
  • U.S. Patent No. 4,845,003 to Kiriu et al. describes the use of acrylic, styrene-butadiene, epoxy, and polyester resins.
  • U.S. Patent No. 3,345,293 to Bartoszewicz et al. describes a rosin-modified phenol- formaldehyde resin, a polystyrene-based resin, and an epoxy resin.
  • It is still another object of the invention to provide a solvation-based method for charging toner particles in a liquid electrophotographic developer composition which involves incorporating into the resinous phase of the toner particle a material containing specific solvation sites effective to solvate a selected metal salt used as the charge director. It is a further object of the invention to provide toner for incorporation into a liquid electro ⁇ photographic developer composition, wherein the toner is formulated with a resinous phase containing a material having such specific solvation sites. It is still a further object of the invention to provide a liquid electrophotographic developer composition containing such a toner and charge director dispersed in an insulating carrier liquid.
  • solvation sites and the metal salt which serves as the charge director are both selected so that very stable, charged toner complexes are formed, i.e., complexes of (i) the cationic, metal component of the charge director and (ii) the toner particle itself.
  • solvation of cations such as metal ions is characterized by the formation of well- known aquo-complexes as
  • Equation (3) may indeed proceed according to the equation
  • the resinous phase of the toner is formulated so that it contains a polymer having the aforementioned solvation sites, which are then present on the surface of the toner particle and thus exposed to and available to solvate charge director in the liquid developer.
  • the resinous phase of the toner is formulated such that it contains monomeric species with such solvation sites, which may or may not be present in combination with a solvating polymer.
  • solvation sites are present on a monomeric species, a polymeric species, or both, it must be emphasized that preferred solvating materials are those which will exothermically solvate the cationic component of the charge director so as to aximize the stability of the resulting charged toner complex and minimize the presence of free, unassociated charge director in solution. Solvation may take place without any significant ionization of the solvation sites.
  • toner which contains, in its resinous phase, a material containing specific solvation sites as just described.
  • a developer composition which contains such toner particles dispersed in an insulating carrier liquid together with a selected metal salt to serve as the charge director.
  • Other aspects of the invention include: processes for manufacturing the above-described toner and developer compositions; consecutive color toning processes making use of solvation-based charge direction; and an electrophotographic image constituting a composite color print prepared using the methods and compositions which will be described in detail herein.
  • Toner as used herein is intended to denote the resinous, colored particles (referred to sometimes herein as “toner particles”) which ultimately form the electrophotographic image on the photoconductive (pc) surface.
  • developer composition as used herein is meant a dispersion of toner and charge director in a selected insulating carrier liquid.
  • the developer composition may contain a number of additional components as will be described below.
  • Particle-mediated conductivity and charge is intended to mean that virtually all of the conductivity and charge in a developer composition derive from the charged toner particles and not from free, unassociated salts which may be present in solution (i.e., from unassociated charge director or other ionizable species) .
  • the developer compositions of the invention display very high particle-mediated conductivity and charge and very low continuous phase conductivity.
  • Consecutive color toning as used herein is intended to mean an electrophotographic development process involving repetition of charging and development steps with more than one color (as outlined in the Background Section above) so as to provide a multicolor final image. The process is also sometimes referred to herein as “consecutive multicolor image development”.
  • Image staining is a problem which is specific to consecutive color toning, and similarly has its art- recognized meaning as used herein. The problem involves overtoning by a second or subsequent process color of an earlier color image in regions where portions of the earlier image should have been discharged but were not. "Image staining” is also sometimes referred to herein and in the art as “character staining”. By “specific solvation sites” is meant moieties present in a material contained within the toner resin and effective to solvate the metal salt or salts which will serve as the charge director.
  • solute unit the charge director, in the present case
  • solvent species the solvation sites on the toner surface herein.
  • solvation may involve chemical or physical interaction, or both, and may vary in degree from a loose complex to a distinct, tightly complexed structure.
  • the solvation sites in the charge director are preferably selected such that solvation of the charge director is a highly exothermic process and gives rise to a very stable, charged toner particle.
  • carboxyl as used herein is meant the carboxylic acid moiety -COOH.
  • the focus of the present invention is on a solvation-based mechanism for providing charge on toner particles contained in a liquid electrophotographic developer composition.
  • the present invention thus involves a novel method of creating very stable charge director/toner complexes.
  • the stability of the charge director/toner complex has been found to be of the utmost importance in liquid electrophotography.
  • the focus was on the use of toners containing surface ion exchange sites effective to form extremely stable, ionic complexes with the metal salts that serve as the charge director.
  • the focus is on a solvation interaction, i.e, the cationic, metal component of the charge director is complexed via solvation to the surface of the toner particle.
  • the toner and the cationic component of the charge director are such that complexation between the two components is heavily favored, as here, virtually all of the charge director will be present in complexed form, and there will be substantially no unassociated charge director in solution.
  • the solvation sites and the charge director are selected such that solvation is a highly exothermic process, giving rise to an extremely stable complex. Examples of particular toner materials and charge directors which may be used in this manner, to provide an extremely stable charged toner particle, are set out in Part (C) of this section.
  • the solvation sites may derive from one or more polymers and/or one or more monomeric species incorporated into the toner resin.
  • the toner resin itself may be a polymer containing the desired solvation sites.
  • Exceptional solvation sites are those which, as noted above, will not ionize to any significant degree under the conditions of ordinary storage and use of the liquid electrophotographic developer.
  • the charge director be either a pH-neutral salt (i.e., a metal salt of a strong acid) or a salt that contains a self-stabilized counterion, as will be described in the next section.
  • ionizable moieties are used as solvation sites, it is preferred that a small amount of acid, preferably the acid form of the charge director's counterion, be added into the developer composition to force equilibrium towards the non-ionized form of the species (in the case of a carboxyl group, the added acid will thus give rise to COOH groups as opposed to the ionized C00 ⁇ species) .
  • acid preferably the acid form of the charge director's counterion
  • the charge director should also be selected with a view towards maximizing the stability of the "solvated" charged toner particle complex. More specifically, the charge director should be a metal salt containing a metal ion which will give rise to a highly exothermic solvation interaction with the aforementioned solvation sites.
  • the preferred metals are generally those which have large negative enthalpies of hydration. The following table illustrates the enthalpies of hydration of some ions:
  • ⁇ Absolute values are based on the assignment of -1091 ⁇ 10 kJ mol "1 to H + (cf. H.F. Halliwell and S.C. Nyburg, Trans. Faraday Soc. , 1963, 59.:1126). Each value probably has an uncertainty of at least lOn kJ mol "1 , where n is the charge of the ion.
  • the present invention involves solvation by materials other than water, and thus does not involve hydration as such. Enthalpies of solvation will, however, typically correlate with these enthalpies of hydration.
  • the enthalpy of solvation here i.e., of the cationic, metal component of the charge director by the solvation sites
  • the enthalpy of solvation here is generally a large negative value (i.e., the solvation reaction involves an enthalpy of solvation that is more negative than about -50 kJ/mole, preferably more negative than about -100 kJ/mole, most preferably more negative than about -500 J/mole) .
  • the present invention encompasses novel toner and developer compositions.
  • the novel toner is useful for formulating a liquid developer composition in which conductivity and charge are both substantially particle-mediated, as explained above.
  • the toner of the invention includes two basic components: (a) resin; and (b) colorant.
  • the present invention involves, as noted above, the incorporation of a material containing specific solvation sites into the resinous phase of the toner particle.
  • Materials which may be incorporated into the resinous phase of the toner particle may be either monomeric or polymeric or both.
  • Preferred monomeric species are those which contain polar moieties as the solvation sites, e.g., sulfhydryl groups, amines, or oxygenic moieties such as hydroxyl groups, carboxyl groups, ketones, amides, and ethers. Most exceptional, however, are hydroxy1- containing monomeric species. Examples of monomeric species which may be incorporated into the toner resin to provide such specific solvation sites include sugars, e.g., mannitol, sorbitol, xylitol and the like.
  • the material containing specific solvation sites be polymeric.
  • Preferred polymers like preferred monomers, are those which contain as the specific solvation sites hydroxyl groups, sulfhydryl groups, carboxyl groups, ketones, amides, ethers, and/or amines.
  • An example of a class of polymers useful herein which contain ketone moieties as the specific solvation sites are acrylates.
  • An example of an amide-containing polymer is nylon, while an exemplary ether-containing polymer is polyethylene oxide.
  • An example of an amino-containing polymer for use herein is polyvinyl pyridine.
  • Examples of particularly preferred polymers for use herein are ethylene-acrylic acid copolymers, ethylene-vinyl alcohol copolymers, styrene-allyl alcohol copolymers, cellulose acetate- butyrate copolymers, hydroxyalkyl aerylate copolymers, and ionomers and mixtures thereof. It will be appreciated by those skilled in the art, however, that a wide range of polymeric materials may be used herein, so long as the selected material enables solvation of the charge director to give a highly stable toner/charge director complex, and does not interact in a deleterious manner with any of the other components of the developer composition.
  • the materials containing specific solvation sites be non-ionized under the conditions used in electrophotographic development, i.e., such that at least about 80%, more preferably at least about 90%, and most preferably at least about 95%, of the solvation sites are not ionized during ordinary conditions of storage and use.
  • the solvation sites are readily ionizable species, such as carboxyl groups, again, as noted above, it is preferred that additional acid be included in the developer composition so that the ionization of the carboxyl groups is suppressed. Typically, this will involve adding the acid form of the charge director counterion.
  • the charge director counterion is diisopropylsalicylate (DIPS)
  • DIPS diisopropylsalicylate
  • the metal ion which serves as the cationic component of the charge director is one that will be solvated exothermically by aforementioned material, e.g., aluminum, magnesium, chromium, iron, or the like.
  • Preferred metals are those which have very negative enthalpies of hydration and thus, herein, give rise to an enthalpy of solvation that is more negative than about -500 kJ/ ol, more preferably more negative than about -1000 kJ/mol.
  • Such values will give rise to a charged toner complex which is extremely stable, in turn enabling preparation of a liquid developer composition having a virtually indefinite shelf-life.
  • This aspect of the invention represents a tremendous advantage relative to currently available developer compositions, which can be relatively unstable and have a finite shelf-life.
  • the colorants which may be used in the toner can include virtually any pigments, dyes or stains which may be incorporated in the toner resin and which are effective to make visible the electrostatic latent image.
  • suitable colorants include: Phthalocyanine blue (C.I. 74160), Diane blue (C.I. 21180), Milori blue (an inorganic pigment equivalent to ultramarine) as cyan colorants; Brilliant carmine 6B (C.I. 15850), Quina- cridone magenta (C.I. Pigment Red 122) and Thio indigo magenta (C.I. 73310) as magenta colorants; benzidine yellow (C.I. 21090 and C.I. 21100) and Hansa Yellow (C.I.
  • the developer compositions of the invention contain the aforementioned toner, together with a selected charge director, as described above, dispersed in an insulating carrier liquid.
  • charge directors include as a counterion the intramolecularly stabilized anion of an ortho-hydroxy aromatic acid, e.g., salicylic acid or a derivative thereof.
  • an ortho-hydroxy aromatic acid e.g., salicylic acid or a derivative thereof.
  • derivative intends to include salicylic acid substituted with one to four, typically one to two, substituents independently selected from the group consisting of lower alkyl (1-6C) , lower alkoxy (1-6C) , halogen, amino, hydroxy, nitro and sulfonate.
  • substituents independently selected from the group consisting of lower alkyl (1-6C) , lower alkoxy (1-6C) , halogen, amino, hydroxy, nitro and sulfonate.
  • charge directors may typically be represented by the formula (RO ) ⁇ 1 (AA ) in which M is a metal atom, AA " represents the anion of the ortho- hydroxy aromatic acid, and R is selected from the group consisting of R-CO-, C 1 ⁇ C 15 alkyl, n is 2, 3 or 4, and x and y are integers the sum of which, clearly, is n.
  • the metal atom "M” may be divalent, trivalent or tetravalent, with those metal atoms that will coordinate most strongly with the toner resin being preferred.
  • AA ⁇ is diisopropyl salicylate ( DIP S)
  • R is c 1 o 21 CO ⁇
  • **-••** • •' R ' is C 1 0 H 2 1 ⁇ ' n is 3
  • x is 1 or 2
  • y is 1 or 2.
  • a second class of charge directors useful herein is described in detail in parent U.S. Patent Application Serial No. 07/546,044, also incorporated by reference.
  • These charge directors are of the formula (X ⁇ ) a M +n (AA ⁇ ) b in which M is a metal atom as described above, AA " represents the anion of an ortho-hydroxy aromatic acid as described with regard to the charge directors of Serial No. 07/464,906, X ⁇ represents the anion of an a, ⁇ -diketone, n is 2, 3 or 4, and a and b are integers the sum of which is equal to n, with the proviso that neither a nor b is 0.
  • the anion X ⁇ represents the anion of an , ⁇ -diketone, one which preferably has the formula:
  • R and R" * are independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, aryl, alkaryl, and haloaryl. If alkyl, alkenyl, alkynyl, cycloalkyl, or haloalkyl, the substituent preferably contains from about 1 to about 12 carbon atoms, more preferably from about 1 to about 6 carbon atoms (wherein the latter type of moiety is sometimes referred to herein as "lower” alkyl, akenyl, alkynyl, etc.).
  • the substituent preferably contains one to about three rings, more preferably, one to two rings, and most preferably is monocyclic.
  • An example of a particularly preferred ⁇ , ⁇ - diketone is acetyl acetone, i.e., wherein R 1 and R2 are both methyl.
  • the developer compositions of the invention contain toner and developer dispersed in an electrically insulating carrier liquid as well-known in the art.
  • the liquid is typically oleophilic, stable under a variety of conditions, and electrically insulating. That is, the liquid has a low dielectric constant and a high electrical resistivity so as not to interfere with development of the electrostatic charge pattern.
  • the carrier liquid has a dielectric constant of less than about 3.5, more preferably less than about 3, and a volume resistivity greater than about 10 9 ohm-cm, more preferably greater than about 10 10 ohm-cm.
  • suitable carrier liquids include halogenated hydrocarbon solvents such as carbon tetrachloride, trichloroethylene, and the fluorinated alkanes, e.g., trichloromonofluoromethane and trichlorotrifluoroethane (sold under the trade name "Freon” by the DuPont Company) ; acyclic or cyclic hydrocarbons such as cyclohexane, n-pentane, isooctane, hexane, heptane, decane, dodecane, tetradecane, and the like; aromatic hydrocarbons such as benzene, toluene, xylene, and the like; silicone oils; molten paraffin; and the paraffinic hydrocarbon solvents sold under the names Isopar G, Isopar H, Isopar K and Isopar L (trademarks of Exxon Corporation) .
  • Toner is prepared by admixing resin and colorant at an elevated temperature, followed by dry comminution. The intermediate particles so provided are then subjected to liquid attrition to give the final toner particles.
  • Resin and colorant are admixed at a temperature in the range of about 70°C to 200°C.
  • a two-roll mill, an extruder, an intensive mixer or the like is used to ensure complete mixing.
  • the admixture is then comminuted dry, i.e., without addition of liquid, to give intermediate particles typically averaging 30 mils in diameter or less.
  • This dry comminution step is carried out in a jet mill, a hammer mill, or the like.
  • the intermediate particles so obtained are then subjected to liquid attrition in a selected attrition liquid to give the final toner particles.
  • the liquid used for attrition is typically selected from the same class of liquids useful as the carrier liquid for the developer composition, as will be described below.
  • the developer compositions of the invention prepared by dispersion of toner and charge director in the insulating carrier liquid — can contain additional materials, e.g., an incompatible phase such as a wax, which is preferably incorporated into the toner at the initial stage of manufacture, i.e., admixed with the colorant, resin, etc., in step (a) (see related application Serial No. 07/464,896).
  • the developer can also contain an antistain agent to reduce the problem of background staining, as discussed in the parent application hereto; again, the antistain agent is preferably incorporated into the composition at the stage of toner manufacture.
  • the developer composition can also contain other materials as known in the art, e.g., dispersants, stabilizers and the like.
  • a consecutive multicolor image development process (or a "consecutive color toning" process) using the materials of the invention may be carried out as follows.
  • the surface of a photoconductive insulating layer on a relatively conductive substrate is charged, and an initial electrostatic charge pattern (or "latent image") is formed on that surface by exposure through a colored transparency.
  • This latent image is then developed with a liquid developer composition of a first color, i.e., comprising toner formulated with a first colorant, typically yellow.
  • the photoconductive layer is then discharged, either optically or non-optically, i.e., via a corona. These steps are then repeated in sequence with developer compositions of different colors, typically (in order) magenta, cyan and black, at which point the developed image may, if desired, be transferred to another substrate, e.g., paper.
  • compositions of the invention i.e., compositions which involve a solvation interaction between the surface of the toner particles and the incorporated charge director, it is possible to carry out the aforementioned sequence of steps without any intermediate processing steps, i.e., rinsing, drying or the like. These steps have typically been necessary in the prior art, as exemplified by the Alexandrovich et al. patent, cited supra, to address the problem of image staining.
  • compositions and processes of the invention address and overcome a number of significant obstacles heretofore present in color electrophotographic image development.
  • RJ-100 a styrene-allyl alcohol copolymer obtained from Allied Chemical Corp. , Morristown, New Jersey
  • RJ-100 a styrene-allyl alcohol copolymer obtained from Allied Chemical Corp. , Morristown, New Jersey
  • To the polymer melt was added 32 g of Heliogen Blue, 3 g of Pigment Green 7 and 0.9 g of Sicofast Yellow D-1155. Mixing was done in 30 minutes, at which time 10 g of carnauba wax was added. After an additional 15 minutes of mixing the mill was cooled and the resultant product was removed. This mixture was cryogenically comminuted on a hammer mill. Thirty g of this powder were charged into an attritor with 130 g of Isopar G (Exxon). After 45 minutes, the attrition was terminated, discharged from the attritor and diluted with 130 g of Isopar to give a 10% concentrate.
  • Isopar G Exxon
  • Example 3 The procedure of Example 1 was repeated, except that RJ-100 was replaced with ACX 260, an ethylene vinyl acetate/vinyl alcohol copolymer (obtained from Allied Chemical Corp.). Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 3
  • Example 1 The procedure of Example 1 was repeated, except that the charge director used, instead of aluminum diisopropyl salicylate, was chromium octoate. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 1 The procedure of Example 1 was repeated, except that the charge director used, instead of aluminum diisopropyl salicylate, was aluminum tri-neodecanoate (Mooney Chemical) . Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • the charge director used instead of aluminum diisopropyl salicylate, was aluminum tri-neodecanoate (Mooney Chemical) .
  • Mooney Chemical aluminum tri-neodecanoate
  • Example 6 The procedure of Example 1 was repeated, except that the charge director used, instead of aluminum diisopropyl salicylate, was copper octoate (Mooney Chemical) . Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • the charge director used instead of aluminum diisopropyl salicylate, was copper octoate (Mooney Chemical) . Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 1 The procedure of Example 1 was repeated, except that the charge director used, instead of aluminum diisopropyl salicylate, was ferric octoate (Mooney Chemical) . Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 1 The procedure of Example 1 was repeated, except that the charge director used, instead of aluminum tri- neodecanoate, was aluminum dinonylnaphthalene sulfonate. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 2 The procedure of Example 1 was repeated, except that the charge director used, instead of aluminum diisopropyl salicylate, was Al(AcAc) (DIPS) 2 , wherein
  • AcAc represents acetyl acetonate
  • DIPS diisopropyl salicylate
  • This charge director was prepared as follows. Aluminum acetyl acetonate (Aldrich Chemical Co., 6.4 g; 0.2 mL) and 8.88 g of diisopropyl salicylic acid (Aldrich Chemical Cc.) were dissolved in 100 g of toluene. The resultant solution was heated at 95-100°C for 2 hours. The solvent was removed at 95°C (steambath) in vacuo, leaving 11.3 g of a viscous glass. The latter was dissolved in 25 mL of hot acetone. Upon removal of the acetone in vacuo, a brittle foam resulted which was dried at 70°C for 24 hours.
  • ACX 251 an ethylene-vinyl alcohol polymer obtained from Allied Chemical
  • ACX 251 an ethylene-vinyl alcohol polymer obtained from Allied Chemical
  • Mixing was continued for 30 minutes.
  • the mill was cooled and the product removed and processed to a 10% concentrate as described in Example 1.
  • To 400 g of 1% working developer was added 0.6 g of a 1% solution of aluminum tri-neodecanoate (Mooney Chemical) .
  • the conductivity was 7.8 pmhos.
  • the shelf-life of the developer was quite superior. This positively charged developer yielded excellent, dense, high resolution images on ZnO photoconductors.
  • Example 10 An ethylene-vinyl alcohol polymer obtained from Allied Chemical
  • Example 9 The procedure of Example 9 was repeated, except that the charge director used, instead of aluminum tri- neodecanoate, was aluminum diisopropyl salicylate. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 9 The procedure of Example 9 was repeated, except that the charge director used, instead of aluminum tri- neodecanoate, was zirconium di-neodecanoate (Mooney Chemical) . Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 9 The procedure of Example 9 was repeated, except that the charge director used, instead of aluminum tri- neodecanoate, was ferric tri-naphthenate (Nuodex) .
  • Example 9 The procedure of Example 9 was repeated, except that the charge director used, instead of aluminum tri- neodecanoate, was Al(AcAc) (DIPS) 2 , wherein "AcAc” and “DIPS" are defined above.
  • the charge director was prepared as described in Example 8.
  • AC 201 resin (Allied Chemical) were placed onto a two-roll mill at 100°C. To the polymer melt was added 52 g of Sicofast D-1155. After 30 minutes of mixing, 60 g of AC 540 resin (Allied) and 60 g of AC 7 (Allied) were added. After 15 minutes of mixing, 10 g of Ethomid HT 60 dispersant (obtained from Akzo) and 13 g of WB-17 dispersant (Petrolite) were added. Mixing was continued for 20 minutes and the product was discharged and processed to give a 10% developer as described in Example 1.
  • AC 201 resin Allied Chemical
  • Example 14 The procedure of Example 14 was repeated, except that the charge director used, instead of aluminum diisopropyl salicylate, was Al(AcAc) (DIPS) - where i n
  • Example 14 The procedure of Example 14 is repeated, except that Sicofast D-1155 is replaced with Hostaperm Red E5B- 02. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 14 The procedure of Example 14 is repeated, except that Sicofast D-1155 is replaced with Heliogen Blue L- 7080. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 14 The procedure of Example 14 is repeated, except that Sicofast D-1155 is replaced with Novaperm Yellow FGL. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality were obtained.
  • Example 14 The procedure of Example 14 is repeated, except that Sicofast D-1155 is replaced with Indofast Brilliant Scarlet R-6335. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 14 The procedure of Example 14 is repeated, except that Sicofast D-1155 is replaced with Quindo Magenta RV6832. Substantially the same results — with respect to stable conductivity, shelf-life, and image quality — were obtained.
  • Example 14 The procedure of Example 14 is repeated, except that Sicofast D-1155 is replaced with Quindo Red 6713.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Liquid Developers In Electrophotography (AREA)

Abstract

L'invention concerne un procédé fondé sur la solvatation qui permet de charger des particules de toner dans une composition de révélateur électrophotographique liquide. Selon ce procédé, on utiliser une matière renfermant des sites de solvatation spécifiques qu'on incorpore dans la phase résineuse du toner, et un directeur de charge qui est un sel métallique dont le composant cationique métallique est efficace pour former un complexe de toner chargé 'solvaté' très stable. L'invention concerne également des compositions de révélateur et de toner qui utilisent le nouveau procédé de direction de charge fondé sur la solvatation.
PCT/US1990/006837 1990-09-12 1990-11-21 Direction de charge fondee sur la solvatation de compositions de revelateur electrophotographique liquides WO1992005476A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP50320791A JP3238148B2 (ja) 1990-09-13 1990-11-21 液状の電子写真用現像剤組成物の溶媒和に基づく電荷制御
CA002092707A CA2092707C (fr) 1990-09-12 1990-11-21 Alimentation en toner, par solvatation, pour compositions liquides de developpement electrophotographique
DE69033748T DE69033748T2 (de) 1990-09-13 1990-11-21 Eine auf solvatation basierende ladungssteuerung von elektro-photograpischen flüssigentwicklerzusammensetzungen
AT91902923T ATE202220T1 (de) 1990-09-13 1990-11-21 Eine auf solvatation basierende ladungssteuerung von elektro-photograpischen flüssigentwicklerzusammensetzungen
EP91902923A EP0548076B1 (fr) 1990-09-13 1990-11-21 Direction de charge fondee sur la solvatation de compositions de revelateur electrophotographique liquides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US582,431 1990-09-12
US58243190A 1990-09-13 1990-09-13

Publications (1)

Publication Number Publication Date
WO1992005476A1 true WO1992005476A1 (fr) 1992-04-02

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EP (1) EP0548076B1 (fr)
JP (1) JP3238148B2 (fr)
KR (1) KR100195463B1 (fr)
AT (1) ATE202220T1 (fr)
AU (1) AU7151691A (fr)
CA (2) CA2092707C (fr)
DE (1) DE69033748T2 (fr)
WO (1) WO1992005476A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016878A1 (fr) * 1991-03-20 1992-10-01 Basf Aktiengesellschaft Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge
EP0636944A1 (fr) * 1993-07-28 1995-02-01 Hewlett-Packard Company Agent de direction de charges positive et chélant pour un révélateur liquide électrographique
WO2003065126A1 (fr) * 2002-01-31 2003-08-07 Hewlett-Packard Indigo B.V. Systeme de transfert d'images et toner liquide associe

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090311614A1 (en) 2006-05-10 2009-12-17 Hewlett-Packard Development Company, L.P. Charge Director for Liquid Toner
JP6609924B2 (ja) * 2015-01-14 2019-11-27 コニカミノルタ株式会社 金属錯体化合物の溶媒和物、それを用いたトナー及びその製造方法、並びに現像剤
JP2019028233A (ja) * 2017-07-28 2019-02-21 富士ゼロックス株式会社 液体現像剤、液体現像剤カートリッジ、画像形成装置及び画像形成方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3753760A (en) * 1970-01-30 1973-08-21 Hunt P Liquid electrostatic development using an amphipathic molecule
US4156034A (en) * 1974-03-20 1979-05-22 Hitachi, Ltd. Liquid developer for electro photography
JPS5987463A (ja) * 1982-11-10 1984-05-21 Dainippon Printing Co Ltd 電子写真用湿式トナ−
JPH01211711A (ja) * 1988-02-19 1989-08-24 Asahi Optical Co Ltd 望遠レンズ
US4957844A (en) * 1989-03-31 1990-09-18 Dximaging Liquid electrostatic developer containing multiblock polymers
US4971833A (en) * 1986-11-03 1990-11-20 Excorim Kb Method of coating solid particles with a hydrophilic gel

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4925766A (en) * 1988-12-02 1990-05-15 Minnesota Mining And Manufacturing Company Liquid electrophotographic toner

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3753760A (en) * 1970-01-30 1973-08-21 Hunt P Liquid electrostatic development using an amphipathic molecule
US4156034A (en) * 1974-03-20 1979-05-22 Hitachi, Ltd. Liquid developer for electro photography
JPS5987463A (ja) * 1982-11-10 1984-05-21 Dainippon Printing Co Ltd 電子写真用湿式トナ−
US4971833A (en) * 1986-11-03 1990-11-20 Excorim Kb Method of coating solid particles with a hydrophilic gel
JPH01211711A (ja) * 1988-02-19 1989-08-24 Asahi Optical Co Ltd 望遠レンズ
US4957844A (en) * 1989-03-31 1990-09-18 Dximaging Liquid electrostatic developer containing multiblock polymers

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992016878A1 (fr) * 1991-03-20 1992-10-01 Basf Aktiengesellschaft Toner electrostatique contenant un compose cetonique comme stabilisateur de la charge
US5338639A (en) * 1991-03-20 1994-08-16 Basf Aktiengesellschaft Electrostatic toner containing a keto compound as a charge stabilizer
EP0636944A1 (fr) * 1993-07-28 1995-02-01 Hewlett-Packard Company Agent de direction de charges positive et chélant pour un révélateur liquide électrographique
WO2003065126A1 (fr) * 2002-01-31 2003-08-07 Hewlett-Packard Indigo B.V. Systeme de transfert d'images et toner liquide associe
US8685610B2 (en) 2002-01-31 2014-04-01 Hewlett-Packard Indigo B.V. Image transfer system and liquid toner for use therewith

Also Published As

Publication number Publication date
AU7151691A (en) 1992-04-15
DE69033748T2 (de) 2001-09-20
JPH06503891A (ja) 1994-04-28
EP0548076A4 (en) 1993-11-10
CA2030585A1 (fr) 1992-03-14
ATE202220T1 (de) 2001-06-15
EP0548076A1 (fr) 1993-06-30
CA2092707C (fr) 2001-06-12
KR100195463B1 (ko) 1999-06-15
JP3238148B2 (ja) 2001-12-10
DE69033748D1 (de) 2001-07-19
EP0548076B1 (fr) 2001-06-13
CA2092707A1 (fr) 1992-03-13

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