EP0456659B1 - Charge director composition - Google Patents

Charge director composition Download PDF

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Publication number
EP0456659B1
EP0456659B1 EP90902057A EP90902057A EP0456659B1 EP 0456659 B1 EP0456659 B1 EP 0456659B1 EP 90902057 A EP90902057 A EP 90902057A EP 90902057 A EP90902057 A EP 90902057A EP 0456659 B1 EP0456659 B1 EP 0456659B1
Authority
EP
European Patent Office
Prior art keywords
charge director
charge
polymer
liquid developer
polar
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
EP90902057A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0456659A1 (en
Inventor
Benzion Landa
Yaacov Almog
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.)
HP Indigo BV
Original Assignee
Hewlett Packard Indigo BV
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 Hewlett Packard Indigo BV filed Critical Hewlett Packard Indigo BV
Publication of EP0456659A1 publication Critical patent/EP0456659A1/en
Application granted granted Critical
Publication of EP0456659B1 publication Critical patent/EP0456659B1/en
Anticipated expiration legal-status Critical
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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
    • G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
    • G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to liquid developer electrostatic photocopying and more particularly to a method of stabilizing charge director solutions and a new stabilized charge director composition.
  • a photoconductive imaging surface is first provided with a uniform electrostatic charge, typically by moving the imaging surface past a charge corona at a uniform velocity.
  • the imaging surface is then exposed to an optical image of an original to be copied.
  • This optical image selectively discharges the imaging surface in a pattern to form a latent electrostatic image.
  • this latent image consists of substantially undischarged "print” portions corresponding to the graphic matter on the original, amidst a "background” portion that has been substantially discharged by exposure to light.
  • the latent image is developed by exposure to oppositely charged, pigmented, toner particles, which deposit on the print portions of the latent image in a pattern corresponding to that of the original.
  • liquid developer photocopiers these charged toner particles are suspended in a liquid developer comprising a carrier liquid, toner particles and charge directors.
  • the entire latent electrostatic image is covered with a thin film of liquid developer from a liquid developer reservoir.
  • the charged toner particles in the liquid developer migrate to the oppositely charged "print” portions of the latent image to form a pattern on the photoconductive surface. This pattern, and the corresponding toner particles, are then transferred to a sheet to produce a visible image. Any liquid developer remaining on the photoconductive surface after this process is recycled back into the liquid developer reservoir.
  • EP-A-001103 describes a method of producing a charge director from a number of components, including a monomer species which is polarised during the process.
  • the charge director is a copolymer soluble in a carrier liquid, and is composed of 1-50% by weight of N-vinyl-2-pyrrolidine and 50 - 99% by weight methacrylic acid ester.
  • DE-A-1930783 describes a polymeric material, an alkylated polymer of heterocyclic vinyl monomer, capable of imparting negative working characteristics to an electrostatic toner.
  • Charge director plays an important role in the developing process described above.
  • the charge director is a chemical species, either molecular or ionic, which acts to control the polarity and charge on the toner particles.
  • the charge director creates charged species causing charging of the imaging material to ensure that the toner particles will be deposited and migrate in such a way as to form the desired image on the imaging surface.
  • Counter ions are also created to keep the liquid developer substantially electrically neutral overall.
  • the present invention may be practised with any number of charge directors, of which lecithin and barium petronate are examples.
  • the charge director molecules form inverse micelles.
  • An example of these micelles is shown in Figure 1.
  • the micelles are formed by aggregation such that the polar portions of the charge director molecules point inside, and the nonpolar portions point outside to decrease the overall surface energy of the system.
  • These micelles may solubilize ions generated by the disassociation of the charge director molecules. It is believed that the solubilization of ions by the charge director micelles is due to the formation within and around the micelles, of a microenvironment having a higher dielectric constant.
  • the solubilization of ions by the charge director micelles results in micelles containing a charged species in their center. Some of the micelles have a positive species in the center and others have a negative species in the center.
  • one object of the present invention is a charge director composition which will resist degradation under the influence of an electric field.
  • Another object of the present invention is a charge director composition which will resist degradation during the replenishment of carrier liquid in a liquid developer dispersion.
  • a further object of the present invention is a charge director solution which will resist destabilization.
  • the present invention is directed to a method of stabilizing a charge director solution as claimed in claim 1 wherein a charge director, a carrier liquid, and a polar monomer molecules are mixed, and subsequently the monomer molecules are polymerized.
  • An initiator species is used to begin the polymerization and the reaction is allowed to proceed to substantial completion.
  • the polar species stabilizes the core of the micelles and reduces the possibility of the micelle rupturing.
  • charge director micelles are associated with insoluble polymer molecules so that the charged species are more stable and less susceptible to degradation. It will be appreciated that by reducing the degradation of the charged species of the liquid developer composition the images formed by the developer will be denser over a longer period of usage, since the presence of the charged species is essential to the electrophoretic imaging process.
  • the present invention is also directed to a charge director composition as claimed in claim 11 and to a liquid developer as claimed in claim 19.
  • a charge director, a solvent, and polar monomer molecules are mixed, and subsequently the monomer molecules are polymerized.
  • An initiator is used to begin the polymerization and the reaction is allowed to proceed to substantial completion.
  • the monomeric molecules of the present invention are soluble in the solvent containing the charge director.
  • the charge director which is at least partially present as micelles, acts as a surfactant for the polymerization of the monomer species. It is believed the monomer species clings to the micelle and polymerizes in the core of the micelle.
  • the selected solvent may be any suitable solvent in which the necessary polymerization may occur.
  • Many nonpolar solvents will work well in the present invention, including: Isopar (a trademarked product of the Exxon Corporation), Isoparafine, hexane, cyclohexane, t-butylbenzene, 2,2,4-trimethylpentane, and normal paraffins.
  • the monomer species chosen may be any unsaturated monomer that is soluble in the selected solvent and polymerizes in the solvent in the presence of an appropriate initiator.
  • the initiator may be any one of a large number of species which will initiate a polymerization reaction, including azobisbutyronitrile, benzoyl peroxide, triphenylazobenzene, cumene hydroperoxide, and t-butyl peracetate.
  • Isopar is heated to approximately 50 degrees C in a reaction vessel fitted with a reflux condenser
  • the reaction is run under a nitrogen atmosphere.
  • Lecithin is slowly mixed into the Isopar.
  • the solution is heated to about 80-90 degrees C and 1-vinyl-2-pyrrolidone is added, followed by a polymerization initiator, e.g., azobisbutyronitrile.
  • the temperature is kept constant, and the reaction is allowed to proceed for about 24 hours.
  • the charge director composition formed by this process will be less subject to degradation of the charge-carrying species than a composition lacking the stabilizing polymer molecules. This superior resistance to degradation will be exhibited both when an electric current is applied to the composition, and when the composition is diluted with solvent (Isopar).
  • a nonpolar solvent in which the 1-vinyl-2-pyrrolidone monomer is soluble, but the polymer is insoluble.
  • the solvent should boil at a significantly higher temperature than 90°C, so that it will remain liquid under the reaction conditions. It is believed that, as the polymerization reaction progresses, the polymer molecules will reach a critical length above which they are insoluble in the solvent; a very fine dispersion of these polymer molecules in the solvent results, and the charge director micelles form around the polymer molecules. The micelles in turn are rigidized and stabilized by the polymer molecules.
  • the critical percent of vinyl pyrrolidone polymer needed to obtain a large stabilization effect is between about 5-9% on a weight-to-weight basis with respect to the charge director solids.
  • Isopar-H Under a nitrogen atmosphere, 1400 grams of Isopar-H was heated to 50 deg. C in a 4-necked, 2 liter, mechanically stirred glass reactor fitted with a reflux condenser. 600 grams of lecithin was dissolved in the Isopar-H by slow addition and stirring. The Isopar-H/Lecithin solution was then heated to 80°C and then 102 grams of 1-vinyl-2-pyrrolidone was added to the solution. Three grams of azobisbutyronitrile suspended in 10-20 ml. of Isopar-H was then added, and the reaction allowed to proceed for 24 hours to completion.
  • Table 1 and Figure 2 show the results of our experiment on the effect of an applied electric field to a common unstabilized charge director, lecithin, solution.
  • Table 1 shows the charge transport in the solution for each pulse.
  • Figure 2 is a graphic representation of the current in the Lantern solution during the time period of the pulse. As shown in Table 1 and Figure 2 the application of an electric pulse to a charge director solution changes the electrical properties of the solution.
  • the applied electric pulse of the experiment is similar to the electric field created during the copying process. Thus, the effect of the electric pulse on the lecithin solution resembles the effect of the electric field created during the copying process of the liquid developer solution.
  • Figure 3 show the conductivity of a composition comprising 17% monomer stabilized species by weight with respect to charge director solids, according to the present invention as compared to a lecithin control, in both cases after addition of a carrier liquid such as Isopar H.
  • the conductivity of the stabilized composition in Isopar remains relatively constant with time, while that of the control decreases with time.
  • the stabilized composition of the present invention is advantageous for use in a photocopier since the conductivity will not change appreciably with time.
  • FIG 4 shows the results of a similar experiment on various stabilized charge director compositions according to the present invention.
  • 800 V. DC pulses were sequentially applied to a cell containing a charge director solution and the total charge transport in the cell was measured for each pulse.
  • the control charge director solution was an unstabilized lecithin solution as used in the above-mentioned experiment.
  • Five stabilized charge director solutions made according to the present invention were also tested. Each charge director solution was made with a different percentage of the monomer stabilizing species.
  • the charge director solution should comprise between 5% and 9% by weight with respect to charge director solids or more of the monomer stabilizing species to achieve a high degree of charge transport constancy.
  • little degradation in charge transport is maintained by a charge director composition comprising 17% monomer stabilizing species by weight with respect to charge director solids.
  • Figure 5 shows the results of an experiment on the decrease in conductivity of a charge director solution during continuous electrophotocopier operation with no paper feed.
  • the lecithin charge director solution shown on the chart is an unstabilized ordinary charge director solution.
  • the other charge director is made according to example 1 of the present invention comprising 17% monomer stabilizing species by weight with respect to charge director solids.
  • the unstabilized lecithin solution had a decrease of an 18picomho/cm in conductivity during the electrophotocopier operation.
  • the solution comprising 17% monomer stabilizing species by weight with respect to charge director solids, made according to example 1 of the present invention showed only a 4picomho/cm decrease in conductivity during continuous electrophotocopier operation.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP90902057A 1989-02-06 1990-01-16 Charge director composition Expired - Lifetime EP0456659B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30615589A 1989-02-06 1989-02-06
US306155 1989-02-06
PCT/US1990/000155 WO1990008983A1 (en) 1989-02-06 1990-01-16 Charge director composition

Publications (2)

Publication Number Publication Date
EP0456659A1 EP0456659A1 (en) 1991-11-21
EP0456659B1 true EP0456659B1 (en) 2004-06-30

Family

ID=23184074

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90902057A Expired - Lifetime EP0456659B1 (en) 1989-02-06 1990-01-16 Charge director composition

Country Status (9)

Country Link
EP (1) EP0456659B1 (ko)
JP (1) JP3076921B2 (ko)
KR (1) KR0180733B1 (ko)
CN (1) CN1041462C (ko)
CA (1) CA2026212C (ko)
DE (1) DE69034151T2 (ko)
HK (1) HK1012439A1 (ko)
MX (1) MX173774B (ko)
WO (1) WO1990008983A1 (ko)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7118842B2 (en) * 2003-09-30 2006-10-10 Samsung Electronics Company Charge adjuvant delivery system and methods

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1930783A1 (de) * 1968-07-10 1970-01-15 Gaf Corp Fluessiger elektrostatischer Pigmentfarbstoff

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA967046A (en) * 1968-08-19 1975-05-06 Gerald S. Lozier Liquid developers for electrostatic printing
DE2740870A1 (de) * 1977-09-10 1979-03-22 Hoechst Ag Fluessigentwickler und hierzu geeignetnr ladungssteuerstoff
US4734352A (en) * 1986-04-22 1988-03-29 E. I. Du Pont De Nemours And Company Polyhydroxy charging adjuvants for liquid electrostatic developers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1930783A1 (de) * 1968-07-10 1970-01-15 Gaf Corp Fluessiger elektrostatischer Pigmentfarbstoff

Also Published As

Publication number Publication date
DE69034151D1 (de) 2004-08-05
HK1012439A1 (en) 1999-07-30
CN1041462C (zh) 1998-12-30
JP3076921B2 (ja) 2000-08-14
KR0180733B1 (ko) 1999-05-01
KR920701871A (ko) 1992-08-12
CN1045304A (zh) 1990-09-12
MX173774B (es) 1994-03-25
CA2026212C (en) 1997-12-02
CA2026212A1 (en) 1990-08-07
DE69034151T2 (de) 2005-06-30
EP0456659A1 (en) 1991-11-21
JPH04503262A (ja) 1992-06-11
WO1990008983A1 (en) 1990-08-09

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