EP0001103A1 - Révélateur liquide et agent de contrôle de charge approprié - Google Patents

Révélateur liquide et agent de contrôle de charge approprié Download PDF

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Publication number
EP0001103A1
EP0001103A1 EP78100815A EP78100815A EP0001103A1 EP 0001103 A1 EP0001103 A1 EP 0001103A1 EP 78100815 A EP78100815 A EP 78100815A EP 78100815 A EP78100815 A EP 78100815A EP 0001103 A1 EP0001103 A1 EP 0001103A1
Authority
EP
European Patent Office
Prior art keywords
liquid developer
developer according
charge control
control agent
copolymer
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
EP78100815A
Other languages
German (de)
English (en)
Other versions
EP0001103B1 (fr
Inventor
Heinz Dr. Herrmann
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.)
Hoechst AG
Original Assignee
Hoechst 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 Hoechst AG filed Critical Hoechst AG
Publication of EP0001103A1 publication Critical patent/EP0001103A1/fr
Application granted granted Critical
Publication of EP0001103B1 publication Critical patent/EP0001103B1/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
    • G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the invention relates to a liquid developer for the development of electrostatic charge images consisting of an electrically insulating carrier liquid of high resistance and low dielectric constant, in which pigment, dye, resinous binder, charge control agent and conventional additives are dispersed or dissolved and a charge control agent.
  • Liquid developers are used in electrophotographic or electrographic copying processes to make latent electrostatic charge images visible. They basically consist of colored particles which are dispersed in a solution of resinous binders and charge control agent in a carrier liquid. In the electric field of the charge image, the colored particles with charge control agent and binder are deposited electrophoretically.
  • the resins which can also be polymers, are combined physically or also chemically, for example by graft polymerization, with the pigment particles (US Pat. No. 3,968,044, DE-OS 25 38 581). This results in particularly stable dispersions.
  • the resins applied to the pigment surface have a certain effect as a charge control agent, which is so significant may be that no addition of charge control agent is required in such pigment dispersions.
  • the charge control substance which is soluble in the aliphatic solvent, is generally absorbed by the pigment particles out of the solution and determines the amount and sign of their charge.
  • the charge control agent has the same effect early as a dispersant. If this is not the case, the liquid developer also contains dispersing agents.
  • Most known charge control agents impart positive charge to the pigment particles. They can be used for the deposition on negatively charged electrostatic charge images; these include in particular metal soaps.
  • Negative charging of the pigment particles is caused by charge control agents, such as lecithin, alkylated polyvinylpyrrolidones, metal salts of long-chain alkylbenzenesulfonic acids or like metal salts of long-chain dialkylsulfosuccinic acid (DE-OS 19 30 784, DE-OS 24 02 953).
  • charge control agents such as lecithin, alkylated polyvinylpyrrolidones, metal salts of long-chain alkylbenzenesulfonic acids or like metal salts of long-chain dialkylsulfosuccinic acid
  • the task was solved by a liquid developer of the type mentioned, which is characterized in that the charge control agent is a copolymer soluble in the carrier liquid, which consists of 1-50 weight percent N-vinyl-2-pyrrolidone and 50-99 weight percent methacrylic acid ester .
  • the copolymer contains 15-40 weight percent N-vinyl-2-pyrrolidone and 60-85 weight percent methacrylic acid ester.
  • the liquid developers mixed with the charge control agents according to the invention develop positively charged, latent electrostatic charge images in a clean and fog-free manner.
  • Copolymers with methacrylic acid esters with alcohol components which carry at least a carbon atom in a straight or branched chain are particularly suitable.
  • 2-ethylhexyl methacrylate, dodecyl methacrylate and octadecyl methacrylate are used as methacrylic acid esters. This additionally ensures that the control substance according to the invention is readily soluble in the carrier liquid and at the same time is an excellent dispersant, by means of which the liquid developer is given good stability.
  • Control materials according to the invention have an advantageously low electrical conductivity. They can therefore be added to the liquid developer in high concentration without reaching disturbing conductivity values. On the other hand, they do not attack photoconductor layers which consist of or contain selenium.
  • Monomers are suitable here which represent acrylic monomers with a polar side group, such as methacrylic acid, acrylic acid amide or hydroxyalkyl methacrylate. They are polymerized in amounts of up to 5 percent by weight.
  • additional monomer component also methacrylic acid with an alcohol component having at most 6 carbon atoms, wherein the co p oly- mer up to 30 per cent by weight of short-chain methacrylic acid ester.
  • the copolymers can be prepared by heating a solution of N-vinyl-2-pyrrolidone and the methacrylic acid ester component in a nitrogen atmosphere with stirring in the presence of a polye manufacture the starter.
  • a starter z. B. azoisobutyronitrile (AIBN) can be used.
  • AIBN azoisobutyronitrile
  • the polymerization temperature depends on the type of starter. AIBN is preferably used in the range from about 70 to 90 ° C.
  • the polymerization takes place in a solvent, which is preferably the same aliphatic hydrocarbon that will later also be the main component of the carrier liquid. If a polymerization component does not dissolve here, the polymerization can of course also be carried out in another solvent, e.g. B. toluene, drain. The solvent used is then stripped off and the remaining polymer is dissolved in the aliphatic hydrocarbon.
  • a solvent which is preferably the same aliphatic hydrocarbon that will later also be the main component of the carrier liquid. If a polymerization component does not dissolve here, the polymerization can of course also be carried out in another solvent, e.g. B. toluene, drain. The solvent used is then stripped off and the remaining polymer is dissolved in the aliphatic hydrocarbon.
  • the charge control agent according to the invention is suitable for the production of all types of liquid developers. So you can z. B. disperse bare carbon blacks in the polymer solution, then add fixing agents - such as soluble resins or polymer organosols - and possibly add a further amount of charge control agent. Instead of the carbon black, you can also use resinated, flushed or polymer grafted carbon blacks or other pigments. In any case, the control agents according to the invention bring about clear negative charging of the pigment particles.
  • the liquid developers can contain, for example, waxes as additives which have a favorable influence on the sedimentation behavior of the liquid developer or the smudge resistance of the developed images. These additives are generally used in amounts corresponding to the pigment content.
  • Highly chlorinated or fluorinated paraffins are particularly suitable as halogen-containing waxes, the latter being obtained by thermal degradation of polytetrafluoroethylene and being soluble in aliphatic hydrocarbons.
  • Examples 1-8 describe the preparation of the charge control substance according to the invention.
  • Examples 9 to 12 relate to liquid developers produced therewith.
  • a 21 4-necked flask equipped according to Example 1 is charged with 600 g of an aliphatic hydrocarbon, boiling range about 160-180 ° C, 390 g of 2-ethylhexyl methacrylate, 90 g of N-vinyl-2-pyrrolidone and 1.8 g of AIBN. After flushing with nitrogen for ten minutes, the mixture is polymerized at 80 ° C. for 5 hours. The resulting viscous polymer solution is cloudy.
  • Example 1 is repeated with the following mixture: 100 g of the aliphatic hydrocarbon, 62.5 g of 2-ethylhexyl methacrylate, 17.5 g of N-vinyl-2-pyrrolidone and 0.3 g of AIBN.
  • the polymerization time is 5 hours. The result is a cloudy polymer solution.
  • Example 1 100 g of an aliphatic hydrocarbon, boiling range about 160-180 ° C., 65 g of 2-ethylhexyl methacrylate, 15 g of N-vinyl-2-pyrrolidone and 0.3 g of AIBN are stirred under a nitrogen atmosphere at an increasing temperature. The heating bath is kept at 65, 70, 75, 80, 85 and 90 ° C for 1 hour.
  • the resulting polymer solution has almost the same properties as the solution according to Example 2.
  • the following mixture is polymerized in the apparatus according to Example 1 for 5 hours at 80 ° C. under nitrogen.
  • a slightly cloudy polymer solution is formed.
  • Example 2 60 g of the graft black suspension produced are stirred with 20 g of the organic polymer dispersion mentioned in Example 1 and with a further 10 g of polymer solution according to Example 2.
  • a good negative liquid developer is obtained by dilution with 2.5 l of an aliphatic hydrocarbon, boiling range 160-180 ° C.
  • 1350 g of the carbon black dispersion obtained are stirred with 60 g of the above-mentioned commercial terpolymer solution, 1350 g of an aliphatic hydrocarbon with boiling range 160 180 ° C. and 12 g of a saturated solution of a chlorinated paraffin with 70% chlorine in the same hydrocarbon.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Liquid Developers In Electrophotography (AREA)
EP78100815A 1977-09-10 1978-09-04 Révélateur liquide et agent de contrôle de charge approprié Expired EP0001103B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2740870 1977-09-10
DE19772740870 DE2740870A1 (de) 1977-09-10 1977-09-10 Fluessigentwickler und hierzu geeignetnr ladungssteuerstoff

Publications (2)

Publication Number Publication Date
EP0001103A1 true EP0001103A1 (fr) 1979-03-21
EP0001103B1 EP0001103B1 (fr) 1981-09-16

Family

ID=6018644

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100815A Expired EP0001103B1 (fr) 1977-09-10 1978-09-04 Révélateur liquide et agent de contrôle de charge approprié

Country Status (5)

Country Link
US (1) US4243736A (fr)
EP (1) EP0001103B1 (fr)
JP (1) JPS5451531A (fr)
AU (1) AU518690B2 (fr)
DE (2) DE2740870A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0037475A1 (fr) * 1980-03-22 1981-10-14 Hoechst Aktiengesellschaft Développateur liquide pour le développement d'images de charge électrostatique
EP0102039A1 (fr) * 1982-08-25 1984-03-07 Hoechst Aktiengesellschaft Révélateur liquide électrophotographique
WO1990008983A1 (fr) * 1989-02-06 1990-08-09 Savin Corporation Composition de controle de charge
WO1990014617A1 (fr) * 1989-05-19 1990-11-29 Spectrum Sciences B.V. Compositions de direction de charge a tolerance d'humidite
US5264313A (en) * 1984-12-10 1993-11-23 Spectrum Sciences B.V. Charge director composition

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374918A (en) * 1981-09-16 1983-02-22 Nashua Corporation Thermally stable liquid negative developer
JPS58203455A (ja) * 1982-05-21 1983-11-26 Canon Inc 静電荷現像用シアントナー及び電子写真法
JPS59102253A (ja) * 1982-12-06 1984-06-13 Ricoh Co Ltd 電子写真用液体現像剤
DE3247925A1 (de) * 1982-12-24 1984-06-28 Hoechst Ag, 6230 Frankfurt Fluessigentwickler fuer die entwicklung elektrostatischer ladungsbilder und verfahren zu seiner herstellung
EP0176629B1 (fr) * 1984-10-02 1988-08-03 Agfa-Gevaert N.V. Révélateur liquide pour le développement d'images électrostatiques
JP2614051B2 (ja) * 1987-09-07 1997-05-28 富士写真フイルム株式会社 電子写真用液体現像剤の製造法
JP2752621B2 (ja) * 1987-09-09 1998-05-18 文化シャッター 株式会社 シャッタの管理制御装置
USH509H (en) 1987-12-22 1988-08-02 Preparation of adhesives
JP2818914B2 (ja) * 1991-04-05 1998-10-30 シャープ株式会社 多目的スチーム発生器
WO2013096206A1 (fr) * 2011-12-21 2013-06-27 Lubrizol Advanced Materials, Inc. Procédé de préparation de polymères acryliques et produits obtenus par ce procédé
JP6484938B2 (ja) * 2014-07-03 2019-03-20 コニカミノルタ株式会社 液体現像剤およびその製造方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1016072A (en) * 1960-11-14 1966-01-05 Gen Aniline & Film Corp Electrophotographic recording process
FR2196489A1 (fr) * 1972-08-15 1974-03-15 Canon Kk
US3876610A (en) * 1969-07-25 1975-04-08 Agfa Gevaert Nv Manufacture of an electrostatic toner material
FR2245986A1 (fr) * 1973-06-27 1975-04-25 Xerox Corp
DE2538581A1 (de) * 1974-09-03 1976-03-11 Ricoh Kk Elektrophotographische suspensionsentwickler
DE2600200A1 (de) * 1975-01-07 1976-07-08 Ricoh Kk Elektrophotographischer suspensionsentwickler

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497705A (en) * 1946-10-16 1950-02-14 Du Pont Copolymerization product of n-vinyl lactams and polymerizable esters, and process for making same
US3044873A (en) * 1958-12-17 1962-07-17 Polaroid Corp Photographic products and processes
US3542681A (en) * 1968-07-10 1970-11-24 Gaf Corp Negative working electrostatic toners
JPS5080136A (fr) * 1973-11-13 1975-06-30
US3993483A (en) * 1974-01-22 1976-11-23 Canon Kabushiki Kaisha Liquid developer for electrostatic image
JPS5140465A (ja) * 1974-10-02 1976-04-05 Enshu Seisaku Kk Shokukinonunomakitorisochiniokeruteichoryokuijisochi
JPS6015063B2 (ja) * 1976-10-26 1985-04-17 オーリン ハント スペシャルティ プロダクツ インコーポレイテッド 電子写真用混合液体ト−ナ−

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1016072A (en) * 1960-11-14 1966-01-05 Gen Aniline & Film Corp Electrophotographic recording process
US3876610A (en) * 1969-07-25 1975-04-08 Agfa Gevaert Nv Manufacture of an electrostatic toner material
FR2196489A1 (fr) * 1972-08-15 1974-03-15 Canon Kk
FR2245986A1 (fr) * 1973-06-27 1975-04-25 Xerox Corp
DE2538581A1 (de) * 1974-09-03 1976-03-11 Ricoh Kk Elektrophotographische suspensionsentwickler
DE2600200A1 (de) * 1975-01-07 1976-07-08 Ricoh Kk Elektrophotographischer suspensionsentwickler

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0037475A1 (fr) * 1980-03-22 1981-10-14 Hoechst Aktiengesellschaft Développateur liquide pour le développement d'images de charge électrostatique
EP0102039A1 (fr) * 1982-08-25 1984-03-07 Hoechst Aktiengesellschaft Révélateur liquide électrophotographique
US5264313A (en) * 1984-12-10 1993-11-23 Spectrum Sciences B.V. Charge director composition
WO1990008983A1 (fr) * 1989-02-06 1990-08-09 Savin Corporation Composition de controle de charge
WO1990014617A1 (fr) * 1989-05-19 1990-11-29 Spectrum Sciences B.V. Compositions de direction de charge a tolerance d'humidite
US5047306A (en) * 1989-05-19 1991-09-10 Spectrum Sciences B. V. Humidity tolerant charge director compositions

Also Published As

Publication number Publication date
JPS649630B2 (fr) 1989-02-17
JPS5451531A (en) 1979-04-23
DE2861086D1 (en) 1981-12-03
DE2740870A1 (de) 1979-03-22
AU518690B2 (en) 1981-10-15
AU3967978A (en) 1980-03-13
EP0001103B1 (fr) 1981-09-16
US4243736A (en) 1981-01-06

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