EP0102025A2 - Développateur électrostatographique à sec et son procédé de fabrication - Google Patents

Développateur électrostatographique à sec et son procédé de fabrication Download PDF

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Publication number
EP0102025A2
EP0102025A2 EP83108097A EP83108097A EP0102025A2 EP 0102025 A2 EP0102025 A2 EP 0102025A2 EP 83108097 A EP83108097 A EP 83108097A EP 83108097 A EP83108097 A EP 83108097A EP 0102025 A2 EP0102025 A2 EP 0102025A2
Authority
EP
European Patent Office
Prior art keywords
weight
parts
toner
dispersion
pigment
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.)
Granted
Application number
EP83108097A
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German (de)
English (en)
Other versions
EP0102025A3 (en
EP0102025B1 (fr
Inventor
Wolfgang Dr. Podszun
Walter Dipl.Phys. Simm
John Dipl.-Ing. Goossens
Carlhans Dr. Süling
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.)
Agfa Gevaert AG
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Agfa Gevaert AG
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Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0102025A2 publication Critical patent/EP0102025A2/fr
Publication of EP0102025A3 publication Critical patent/EP0102025A3/de
Application granted granted Critical
Publication of EP0102025B1 publication Critical patent/EP0102025B1/fr
Expired legal-status Critical Current

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Classifications

    • 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 invention relates to an electrostatographic suspension developer, based on pigment particles coated with crosslinked precipitation polymer, and to a method for producing the developer.
  • Dry and wet development methods are known for developing electrostatic images on electrostatographic recording materials.
  • the wet development processes are superior to the dry development processes with regard to edge sharpness and resolving power, especially in color copying processes.
  • the known electrostatographic suspension developers are generally prepared by pigment particles together with soluble polymer and in a highly insulating carrier liquid a charge-determining substance, also called a control substance.
  • the polymer is absorbed by the pigment particles, producing what is known as a toner, and gives the pigment dispersion formed (usually referred to as a toner dispersion) a certain stability.
  • Such liquid developers have been widely used in electrostatographic processes. However, they have a number of disadvantages.
  • the presence of non-adsorbed polymer in the carrier liquid is particularly disadvantageous, the proportion of which is increased when the used toner is replaced by the addition of developer concentrate when the toner dispersion is used for image development.
  • the enrichment of the dissolved polymer then leads to changes in the electrostatographic properties of the developer and thus to a deterioration in quality.
  • This disadvantage is linked to the existing adsorption-desorption equilibrium and is therefore unavoidable when using soluble polymer.
  • DE-A 2 157 143 describes a process for the preparation of an electrostatographic suspension developer by graft polymerization of acrylic ester monomers Pigment known.
  • graft polymerization reactions have the disadvantage that, in addition to the graft polymerization, there is also an "ordinary" homopolymerization or copolymerization and in this way, in addition to the desired grafting product, homopolymer or copolymer which is not anchored to the pigment is formed.
  • Elaborate separation processes are necessary to display the graft product.
  • a further difficulty is that the grafting yield depends to a large extent on the type of the grafting substrate, which makes it difficult to provide similar, differently colored suspension developers for color copying processes.
  • DE-B 1 933 362 describes the shell-like coating of pigments with polymers.
  • An inner insoluble polymer shell and an outer shell swellable in the carrier liquid are applied to the pigment.
  • the polymers used are uncrosslinked. They are produced in the absence of the pigment by bulk polymerization and applied to the pigment as a solution (e.g. in toluene) or as a melt.
  • the particle size is adjusted by grinding in a ball mill.
  • a disadvantage of this process is that relatively coarse toner particles (approx. 0.09 mm) which limit the resolving power are obtained.
  • DE-A 2 026 390 describes the production of toner particles by polymerizing synthetic resin monomers and coloring materials by the process known as suspension polymerization.
  • the polymer particles obtained in this way are primarily suitable for use as dry developers due to their particle size and other properties.
  • GB-A 868 974 describes a liquid electrostatographic developer containing toner particles which are precoated with a polymer of an acrylic or methacrylic acid ester of hydrogenated abietyl alcohol.
  • the polymer is prepared separately or synthesized in the presence of the pigment by a bulk polymerization process.
  • the T eilchen Anlagennspektrum Developer is relatively wide, which becomes disturbing when playing the tonal values.
  • the invention is based on the object includes an electrostatographic suspension developer which finely divided polymer-coated pigment particles having an improved storage stability and can be used with advantage for arbkopierphal F to provide.
  • Another object of the invention is a method for producing an electrostatographic suspension developer by precipitation polymerization in a carrier liquid as defined above in the presence of the pigment.
  • the precipitation polymer formed according to the invention is firmly anchored on the pigment surface and has the fine structure typical of precipitation polymers, which can be made visible, for example, by scanning electron microscope images.
  • the suspension developers according to the invention have excellent dispersion stability, which does not change during use and storage.
  • the method for preparing the suspension developer according to the invention has the advantage over the previously used method has the advantage that the operations to be carried out separately: Polymerisather too, P igmentumhüllung, milling and dispersion are reduced in number and are combined into a single operation.
  • a pigment dispersion in an electrically insulating liquid suitable as a carrier liquid is assumed.
  • the pigments used in the customary electrostatographic suspension developers are suitable as pigment particles. These include e.g. Azo dyes, xanthene dye, phthalocyanine dyes, such as DE-A 2 944 021 describes triphenylmethane dyes, acridine dyes, quinoline dyes, quinonimine dyes, thiazine dyes or azine dyes.
  • Spirit black C.I. No. 50415), aniline black (C.I. No. 50440), cyanine blue (C.I. No. 74250), brilliant carmine 6 B (C.I. 15850), real red (C.I. No.
  • Carbon black C.I. No. 77266
  • Helio real blue HG C.I. No. 74160
  • Fanalrosa B C.I. No. 45160
  • Helio real yellow GRN C.I. No. 21100
  • Electrically insulating liquids with a volume resistance of at least 10 9 ohm'cm and a dielectric constant below 3, preferably based on hydrocarbons, are used as the liquid component or carrier liquid for the pigment dispersion, for example aromatic hydrocarbons such as benzene, toluene or xylenes or aliphatic C 6 -C 15 hydrocarbons such as n-hexane, cyclohexane, n-heptane, n-octane or decalin. Mixtures of different hydrocarbons can also be used. Branched aliphatic hydrocarbons such as isodecane and isododecane are particularly suitable.
  • the proportion by weight of the pigment should be 0.5 to 50%, preferably 5-30%, based on the pigment dispersion.
  • the pigment dispersion can be used without stabilizing additives. In many cases, however, it is advantageous to pre-stabilize the dispersion by adding small amounts (0.05-15% by weight, based on the pigment content) of a soluble polymer.
  • Homopolymers or copolymers of (meth) acrylic acid esters are suitable for this purpose, for example a 1: 1 copolymer of isobutyl methacrylate and lauryl methacrylate.
  • Copolymers with a proportion of 0.1-10% by weight of copolymerized monomers with -OH, -COOH, -NH 2 , -NHR, -NR 2 groups, such as 2-hydroxyethyl methacrylate, (meth) are also very suitable.
  • acrylic acid (meth) acrylamide, NN-dimethylacrylamide, N, N-dimethylaminoethyl methacrylate and N-vinylpyrrolidone.
  • the preferred molecular weight is in the range of 50,000 to 250,000.
  • (Meth) acrylic acid esters (A) with 8-24 carbon atoms in the alcohol part are understood to mean the esters of acrylic acid or methacrylic acid and straight-chain and branched C 8 -C 24 alkanes, examples being: 2-ethylhexyl methacrylate, decyl methacrylate, dodecyl methacrylate, Lauryl methacrylate and stearyl methacrylate.
  • Crosslinkers (B) are e.g. polyfunctional (meth) acrylates, such as ethylene di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, glycerol trimethacrylate and trimethylolpropane trimethacrylate, but also divinylbenzene and allyl methacrylate are suitable.
  • polyfunctional (meth) acrylates such as ethylene di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, glycerol trimethacrylate and trimethylolpropane trimethacrylate, but also divinylbenzene and allyl methacrylate are suitable.
  • (meth) acrylic acid esters with 1-7 C atoms in the alcohol part are suitable as component (C).
  • Compounds suitable as component (D) are, for example, hydroxy and (optionally N-alkyl-substituted) aminoalkyl methacrylates such as 2-hydroxyethyl methacrylate or N, N-dimethylaminoethyl methacrylate, further styrene, vinyl toluene, ⁇ -methylstyrene, maleic anhydride, vinyl acetate, allyl alcohol and vinyl pyrrolidone.
  • the ratio of pigment to the total amount of monomers should be 3: 1 to 1:10, preferably 2: 1 to 1: 5.
  • R adikal horrinsky, particularly peroxides and Azoverbinschreibgen are suitable.
  • examples include: aliphatic azodicarboxylic acid derivatives such as azobisisobutyronitrile or azodicarboxylic acid esters, peroxides such as lauroyl peroxide, succinyl peroxide, dibenzoyl peroxide, p-chlorobenzoyl peroxide, ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, tert-butyl peroxide, cyclohexanone peroxide, cyclohexanone peroxides, Mono-tert-butyl permaleinate, percarbonates such as dicyclohexyl and diisopropyl percarbonate, dialkyl peroxides such as di-tert-butyl peroxide,
  • a combination of different starting components for example starting components with different decay temperatures, can also be used with advantage in many cases.
  • polymerizable radical starters is advantageous if the release of decomposition products of the starter into the liquid phase is to be prevented.
  • Suitable starting components of this type are, for example, dimethacryloyl peroxide and p, p'-divinylbenzoyl peroxide (US Pat. No. 2,593,399).
  • the reaction temperature depends on the type of starting component used, it is generally in the range of 50-150 ° C.
  • the polymerization reaction can be carried out either under normal pressure or under positive pressure. The use of negative pressure can be indicated as a degassing stage after the reaction has ended.
  • the precipitation polymerization reaction can be carried out by a "batch process".
  • the monomers and the starting component are added to the pigment dispersion all at once and the reaction is initiated by increasing the temperature. In this way, pigment particles with a largely uniform polymer shell are obtained.
  • the monomers and the starting components are metered in during the polymerization.
  • This embodiment opens up a number of technically very interesting possibilities. So you can ignore change and build in this way a cup-shaped Polymerisathülle as the monomer composition over the D osierzeitraum. It is possible, and in certain cases sensible, to first set the crosslinker content high and then to lower it during the metering period. With this procedure, a slightly crosslinked outer shell is obtained which is more swellable than the inner shell. Pigment particles constructed in this way are notable for high dispersion stability.
  • (D) contains polar groups such as -OH, -NH 2 , -COOH, preferably at the start of the polymerization, and thus to polymerize these monomers in the vicinity of the pigment surface .
  • the starting component is also advantageously metered in over the reaction period.
  • Solid starting components are expediently dissolved in solvents or monomers.
  • the pigment dispersion is mixed by shaking or stirring, including that
  • the turnover should therefore be at least 80%. It can be influenced in a known manner by the reaction time, the reaction temperature and the concentration of the starting component.
  • the coated pigment particles have an average particle size of 0.2 to 2 ⁇ m.
  • the dispersion obtained by precipitation polymerization according to the present process can be diluted to the desired working concentration, for example to 0.01% to 1%, by adding further carrier liquid. On this occasion, if desired, the present carrier liquid can be exchanged for another.
  • the organic group preferably contains a chain of at least 4 carbon atoms, in particular 10 to 18 carbon atoms, and it can also be substituted and / or interrupted by one or more heteroatoms, e.g. through oxygen, sulfur or nitrogen.
  • the solubility of the metal salts described in the electrically insulating carrier liquid can be determined by one or more organic groups of branched structure, e.g. are promoted by branched aliphatic groups such as a 2-butyloctyl group.
  • Suitable positive charge control agents contain a metal alkyl sulfonate in which the metal ion is one of the divalent metal ions zinc (II), lead (II), cadmium (II) or copper (II) or a trivalent metal ion from group VIII of the periodic table, for example iron (III), or from the group VIB, for example chromium (III), and in which the sulfonate group is present directly on a straight-chain alkyl chain with at least 6 carbon atoms.
  • the metal ion is one of the divalent metal ions zinc (II), lead (II), cadmium (II) or copper (II) or a trivalent metal ion from group VIII of the periodic table, for example iron (III), or from the group VIB, for example chromium (III), and in which the sulfonate group is present directly on a straight-chain alkyl chain with at least 6 carbon atoms.
  • control substance is either added to the concentrate of the suspension developer or when the developer is diluted to the desired working concentration.
  • the cheapest amount can easily be determined by simple experiments.
  • Zinc mono (2-butyl) octyl phosphate is preferred as the control substance.
  • fixatives are incorporated into the finished developer.
  • Suitable fixing substances are resins which are said to be compatible with the binding material of the photoconductive recording material, e.g. with the binder of a photoconductive zinc oxide layer, so that good adhesion of the generated image to the base is obtained after development.
  • Suitable resins are esters of hydrogenated rosin and fatty oil varnish ("long-oil"), rosin-modified phenol-formaldehyde resin, pentaerythritol esters of rosin, glycerol esters of hydrogenated rosin, ethyl cellulose, various alkyd resins, polyacrylic and polymethacrylic resin, polystyrene, poly (vinyl acetate), poly (vinyl acetate). Specific examples of such resins can be found in the literature on electrostatographic suspension developers, e.g. in BE-A 699 157 and in GB-A 1 151 141.
  • a pigment dispersion prepared with the aid of a ball mill made of 30 g helio-real yellow GRN (CI 21100), 270 g isododecane and 0.3 g polylauryl methacrylate (MW 150000), was introduced and heated to 80 ° C.
  • the dispersion was gassed with N 2 , stirred at 500 rpm, and 0.5 g of azoisobutyronitrile (AIBN) was added.
  • AIBN azoisobutyronitrile
  • the dispersion was diluted with isododecane to a solids content of 4% by weight and 12 mg of zinc mono- (2-butyl) octyl phosphate per gram of solid were added.
  • the charge of the toner particles was stabilized after 24 hours of storage.
  • the particle size was 0.8-1.2 pm.
  • Example 2 A dispersion of 35 g of Helioechtblau HG (CI 74160) and 315 g of isododecane was placed in the apparatus described in Example 1. The dispersion was stirred at 60 ° C. at 600 rpm added continuously over a period of 60 minutes. The temperature was then kept at 70 ° C. for 1 hour and, after addition of 0.88 g of dibenzoyl peroxide, stirring was continued at 80 ° C. for 2 hours. A stable dispersion resulted.
  • Example 1 of DE-A 2 157 143 50 g of the ester of methacrylic acid were reacted with oleyl alcohol, 50 g of finely ground Helio real yellow GRN (C.I. 21100) and 1 g of azobisisobutyronitrile in benzene.
  • the reaction product was freed from soluble constituents by repeated pouring into methanol and poured into. dispersed the isoparaffinic solvent specified in said DE-A.
  • the dispersion obtained showed insufficient stability for practical use.
  • the toner particles tend to agglomerate and sediment.
  • the developer delivers unclean images by depositing toner in the non-image areas.
  • Example 1 of DE-B 1 933 362 Helioechtblau HG (C.I. 74160) was coated with 2 plastic layers.
  • the granules obtained were ground in a ball mill to a particle size of -0.09 mm and dispersed in isododecane.
  • the suspension obtained was suitable in principle for developing latent electrostatic images, but the resolution of the images achieved with the developer was inadequate and in particular inadequate for the reproduction of color images.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Liquid Developers In Electrophotography (AREA)
EP83108097A 1982-08-28 1983-08-17 Développateur électrostatographique à sec et son procédé de fabrication Expired EP0102025B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823232062 DE3232062A1 (de) 1982-08-28 1982-08-28 Elektrostatographischer suspensionsentwickler und verfahren zu dessen herstellung
DE3232062 1982-08-28

Publications (3)

Publication Number Publication Date
EP0102025A2 true EP0102025A2 (fr) 1984-03-07
EP0102025A3 EP0102025A3 (en) 1985-10-23
EP0102025B1 EP0102025B1 (fr) 1987-09-23

Family

ID=6171935

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83108097A Expired EP0102025B1 (fr) 1982-08-28 1983-08-17 Développateur électrostatographique à sec et son procédé de fabrication

Country Status (5)

Country Link
US (1) US4521505A (fr)
EP (1) EP0102025B1 (fr)
JP (1) JPS5958441A (fr)
CA (1) CA1248390A (fr)
DE (2) DE3232062A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5264313A (en) * 1984-12-10 1993-11-23 Spectrum Sciences B.V. Charge director composition
DE3514867A1 (de) * 1985-04-25 1986-11-06 Agfa-Gevaert Ag, 5090 Leverkusen Elektrostatografischer suspensionsentwickler und verfahren zu dessen herstellung
JPS63178258A (ja) * 1987-01-19 1988-07-22 Mitsubishi Paper Mills Ltd 静電写真用液体現像剤
US4758492A (en) * 1986-04-30 1988-07-19 Eastman Kodak Company Weakly acidic crosslinked vinyl polymer particles and coating compositions and electrographic elements and developers containing such particles
DE3642212A1 (de) * 1986-12-10 1988-06-23 Espe Stiftung Polymerisierbare massen, verfahren zu ihrer herstellung und ihre verwendung als dentalmassen
US4966824A (en) * 1988-06-06 1990-10-30 Spectrum Sciences Liquid toner composition containing two different charge directors
US4947201A (en) * 1988-06-06 1990-08-07 Spectrum Sciences Imaging system
US5155001A (en) * 1989-03-06 1992-10-13 Spectrum Sciences B.V. Liquid developer method with replenishment of charge director
JP4122690B2 (ja) * 2000-07-28 2008-07-23 日本ゼオン株式会社 トナーの製造方法
DE60140850D1 (de) * 2000-11-10 2010-02-04 Samsung Electronics Co Ltd Oberflächenbehandelte Farbstoffteilchen enthaltende Flüssigtinten und ihre Herstellungsverfahren
JP2004002501A (ja) * 2002-05-27 2004-01-08 Fuji Photo Film Co Ltd インクジェットプリンタ用油性インク組成物
JP2004018736A (ja) * 2002-06-18 2004-01-22 Fuji Photo Film Co Ltd インクジェットプリンタ用油性インク組成物
JP2004035592A (ja) * 2002-06-28 2004-02-05 Fuji Photo Film Co Ltd インクジェットプリンタ用油性インク組成物、電子写真用液体現像剤及び着色樹脂粒子の製造方法
WO2009070148A1 (fr) * 2007-11-30 2009-06-04 Hewlett-Packard Development Company, L.P. Pigments pour encres en poudre à revêtement polymère pour impression électrophotographique
MY177835A (en) 2012-12-21 2020-09-23 Quarzwerke Gmbh Thermotropic polymers

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3668127A (en) * 1968-07-01 1972-06-06 Ricoh Kk Liquid developer for electrophotography
GB1319815A (en) * 1969-05-28 1973-06-13 Fuji Photo Film Co Ltd Preparation of electrophotographic developers
GB1411287A (en) * 1972-07-12 1975-10-22 Agfa Gevaert Liquid electrophotographic developers
JPS5612868B2 (fr) * 1973-03-23 1981-03-25
US4156034A (en) * 1974-03-20 1979-05-22 Hitachi, Ltd. Liquid developer for electro photography
JPS548532A (en) * 1977-06-22 1979-01-22 Toray Industries Wet toner with good fixability
DE2946465A1 (de) * 1979-11-17 1981-06-11 Agfa-Gevaert Ag, 5090 Leverkusen Neue polymere, verfahren zu ihrer herstellung und ihre verwendung zur herstellung fotografischer emulsionen sowie fotografische materialien
JPS5858667B2 (ja) * 1979-12-03 1983-12-26 株式会社リコー 静電写真用液体現像剤
JPS58150970A (ja) * 1982-03-04 1983-09-07 Ricoh Co Ltd 静電写真用液体現像剤

Also Published As

Publication number Publication date
US4521505A (en) 1985-06-04
CA1248390A (fr) 1989-01-10
EP0102025A3 (en) 1985-10-23
DE3373845D1 (en) 1987-10-29
JPS5958441A (ja) 1984-04-04
EP0102025B1 (fr) 1987-09-23
DE3232062A1 (de) 1984-03-01

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