US3625897A - Liquid developing agent for electrophotography - Google Patents

Liquid developing agent for electrophotography Download PDF

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Publication number
US3625897A
US3625897A US832416A US3625897DA US3625897A US 3625897 A US3625897 A US 3625897A US 832416 A US832416 A US 832416A US 3625897D A US3625897D A US 3625897DA US 3625897 A US3625897 A US 3625897A
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US
United States
Prior art keywords
liquid
carrier liquid
developing agent
solution
acid
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
US832416A
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English (en)
Inventor
Hazime Machida
Zenjiro Okuno
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Ricoh Co Ltd
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Ricoh Co Ltd
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Publication date
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Publication of US3625897A publication Critical patent/US3625897A/en
Anticipated expiration legal-status Critical
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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/12Developers with toner particles in liquid developer mixtures
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/001Electric or magnetic imagery, e.g., xerography, electrography, magnetography, etc. Process, composition, or product
    • Y10S430/105Polymer in developer

Definitions

  • a liquid developing agent for electrophotography comprising a mixed solution consisting of an insulating carrier liquid containing an organic substance having carboxyl group and a colored solution prepared by solving or dispersing a dye and an amine in a polar solvent which is not miscible with the aforementioned carrier liquid.
  • the present invention relates to an improvement of liquid developers for electrophotography.
  • electrophotograph used in the specification is intended to mean a visible reproduction of a so-called electrostatic latent image such as a latent image formed by extinguishing the charge in the exposed area and preserving the charge in the not exposed area by exposure of the photoconductive substances through the original.
  • electrostatic latent image such as a latent image formed by extinguishing the charge in the exposed area and preserving the charge in the not exposed area by exposure of the photoconductive substances through the original.
  • the copying material was previously impressed, by corona discharge, with. an electrical charge all over the photoconductive substance.
  • the polarity-controlling agent behaves in such a way as to give the coloring particles the polarity necessary for them to stick fast to the electrostatic latent image and to act as a dispersing agent for achieving the colloidal stability of the liquid developer, and said agent also has a property of fixing the copied image after the development has been completed.
  • Organic hydrocarbon solvents are generally used as a carrier liquid of the liquid developer of this type but they have a defect of being inflammable.
  • carrier liquids one of which comprises a halogenated hydrocarbon and the other of which comprises fluorinated hydrocarbons, both being free from inflammability; however, they have their respective defects, the former being not satisfactory because of its toxicity and the latter because of its high price.
  • This liquid developer only aims at eliminating inflammability of the liquid developer by emulsifying water therein by the use of an emulsifying agent, which results in the presence of unnecessary minute water beads which make no contribution to the development of the electrostatic latent image, in the liquid developer wherein a solution of high resistance and low dielectric constant is used as a carrier liquid.
  • Liquid developers of this type have no satisfactory emulsion stability and since they are substantially prepared according to a method in which the coloring particles which have absorbed not so much controlling agent are deposited electrostatically on the latent image, the resultant image does not have very good fixedness.
  • the present invention relates to a liquid developing agent for electrophotography comprising a mixed solution consisting of a carrier liquid containing an organic substance having a carboxyl group and a colored solution prepared by solving or dispersing a dye and an amine in a polar solvent which is not miscible with the aforementioned carrier liquid.
  • a polar solvent immiscible with a carrier liquid that can be used in this invention there are enumerated water, alcohols, acetone, methyl cellosolve, dimethyl-formamide and dioxane.
  • dyes in addition to dyes which are either soluble or insoluble in the aforementioned polar solvent and are insoluble in the carrier liquid, for
  • Acid Blue 119 carbolan crimson (C.l. Acid Red 138), carbolan blue (C.l. Acid Blue 138) and the like, such dyes as aniline black (CI. Pigment Black 1), spirit black (C.I. Solvent Black 5) and the like having an amino group which coordinates with carboxylic acid can be used effectively.
  • the amine to be used it should be an amine of such type as to coordinate with carboxylic acid, namely a tertiary amine to be converted to a quaternary salt compound by coordinating with a carboxyl group.
  • the amine is required to be soluble in the aforementioned polar solvent and immiscible with the carrier liquid.
  • Trimethylamine, triethylamine and triethanolamine, for instance may be mentioned as being suitable.
  • the organic substance having a carboxyl group and which is to be dissolved in the carrier liquid besides acrylic acid, polymers and copolymers such as acrylates or methacrylates which contain methacrylic acid, and such unsaturated resins as alkyd resin, maleic acid resin and the like, varnish, rosin and such higher fatty acids as stearic acid and oleic acid can be used.
  • acrylic acid polymers and copolymers such as acrylates or methacrylates which contain methacrylic acid, and such unsaturated resins as alkyd resin, maleic acid resin and the like, varnish, rosin and such higher fatty acids as stearic acid and oleic acid
  • any of the chemicals such as naphtha, isoparaffin and paraffin, that have hitherto been commonly used as a carrier liquid of liquid developers can be used in practising this invention.
  • the procedure to make the liquid developing agent according to the present invention consists of preparing a colored solution obtained by solving or dispersing the aforementioned dyes and amine in a polar solvent and a solution obtained by solving an organic substance which has a carboxyl group in a carrier liquid. Both of the solutions are mixed and stirred fully with a mixer like a homogenizer until a developer of a perfectly homogenized emulsion or suspension is obtained.
  • the quantity of amine to be added can be decreased to such a degree as to make the amine existing in the colored solution in sufficient quantity to enable it coordinate with the carboxyl group of the organic substance dissolved in the carrier liquid.
  • the emulsification can be promoted by making the colored solution a fatty acid ammonium salt with by the addition of fatty acid beforehand or by using a proper surface active agent if the emulsification or suspension is found to be imperfect.
  • the developing agent according to the present invention is an emulsion or suspension of a colored polar solution which contains an amine and a solution of a high resistance and low dielectric constant which contains carboxyl group. It is important to determine the ratio of the ingredients of the developing agent in such a way as to present a distinct polarity when the electrostatic latent image is developed. To achieve this purpose it is necessary to mix more than one part by weight of the carrier liquid with one part by weight of the colored solution.
  • a developing agent wherein water is specifically used as a polar solvent to solve the dye is perfectly free from inflammability.
  • the developing agent prepared according to the present invention possesses many excellent merits such as greatly improved dispersibility and stability when compared with those conventional developing agents which are prepared by simply dispersing the polar solvent, in which dyes are solved, in the carrier liquid, since the carboxyl-containing organic substance in the carrier liquid coordinates with the amine contained in the colored solution in which dyes are solved to display an excellent surface activity, and the fixing property of the image is improved very much due to the highly polymerized substance abundantly contained in the developing agent.
  • EXAMPLE 1 A paste was prepared by mixing a solution, which had been obtained by solving 1 g. of water-soluble carbolan crimson (anthraquinone acid dye manufactured by l.C.1.) in g. of 1 percent trimethylamine-naphthenic acid aqueous solution, 3 percent (by weight) acrylate copolymer and l00 g. of
  • EXAMPLE 2 B solution was prepared by mixing a solution obtained by solving 125 g. of water soluble carbolan green (anthraquinone acid dye manufactured by l.C.l.) in 150 g. of 1 percent triethanolamine-oleic acid aqueous solution, 3 percent copolymer of styrene methacrylic acid butyl acrylate (mole ratio 50:30:20) and toluene in the homogenizer for minutes. Ten parts of this B solution was dispersed in 50 parts of naphtha No. 6 to obtain the developing agent. The developing property. of the developer thus obtained was not destroyed when the quantity of B solution dispersed in the developer was not in excess of 30 parts.
  • EXAMPLE 3 One g. of spirit black was mixed with 100 g. of 1 percent triethyl-amine-stearic acid aqueous solution with the homogenizer. This mixture 5 percent copolymer of ethyl acrylate-vinyl benzoic acid-lauryl methacrylate and 50 g. of toluene were mixed with the homogenizer to obtain C solution. Ten parts of this C solution was dispersed in 50 parts of lsopar H to prepare the developing agent. N0 damage of the developing property was observed so far as the quantity of the dispersed C solution remained within the region of 30 parts.
  • EXAMPLE 4 One g. of aniline black was solved in 100 g. of 1 percent trimethylamine-naphthenic acid. Twenty parts of this solution was dispersed in 50 parts of naphtha No. 6 'to obtain the developing agent.
  • a liquid developer for electrophotography comprising a carrier liquid selected from the group consisting of toluene, carbon tetrachloride, naphtha and isoparaffic and paraffinic hydrocarbons, said carrier liquid having emulsified or suspended therein a colored solution or dispersion of a dye and a polar solvent, saiddye being selected from the group consisting of alkali blue (C.l. Acid Blue 119), carbolan crimson (C.I. Acid Red 138), carbolan blue (C.l. Acid Blue 138), aniline black (CI. Pigment Black 1), and spirit black (C.l.
  • a carrier liquid selected from the group consisting of toluene, carbon tetrachloride, naphtha and isoparaffic and paraffinic hydrocarbons
  • said carrier liquid having emulsified or suspended therein a colored solution or dispersion of a dye and a polar solvent, saiddye being selected from the group consisting of al
  • Solvent Black 5 said polar solvent being selected from the group consisting of water, acetone, methyl cellosolve, dimethylformamide and dioxane, the improvement in which said colored solution or dispersion contains dissolved therein a tertiary amine selected from the group consisting of trimethylamine, triethylamine and triethanolamine, and said carrier liquid contains dissolved therein a carboxyl-containing organic material selected from the group consisting of acrylic acid, acrylate copolymer containing methacrylic acid, methacrylate copolymer containing methacrylic acid, alkyd resin, maleic acid resin, varnish, rosin, stearic acid, oleic acid, styrenem ethacrylic acid-butyl acrylate copolymer and ethyl acrylatevinyl benzoic acid-lauryl methacrylate copolymer, the weight of said carrier liquid present in said developer liquid being greater than the weight of the colored solution or dispersion present'in said

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US832416A 1968-06-19 1969-06-11 Liquid developing agent for electrophotography Expired - Lifetime US3625897A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4188568 1968-06-19

Publications (1)

Publication Number Publication Date
US3625897A true US3625897A (en) 1971-12-07

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ID=12620714

Family Applications (1)

Application Number Title Priority Date Filing Date
US832416A Expired - Lifetime US3625897A (en) 1968-06-19 1969-06-11 Liquid developing agent for electrophotography

Country Status (5)

Country Link
US (1) US3625897A (xx)
BE (1) BE734824A (xx)
DE (1) DE1931129C3 (xx)
GB (1) GB1282892A (xx)
NL (1) NL6909386A (xx)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3772053A (en) * 1972-09-22 1973-11-13 Eastman Kodak Co Electrographic formation of dye images
US3885960A (en) * 1972-12-11 1975-05-27 Bell & Howell Co Method of development of liquid electrostatic images using an hydrophobic barrier liquid
US3954640A (en) * 1973-06-27 1976-05-04 Xerox Corporation Electrostatic printing inks
US4097391A (en) * 1975-10-24 1978-06-27 A. B. Dick Company Liquid developer for electrophotographic offset masters
US4476210A (en) * 1983-05-27 1984-10-09 Xerox Corporation Dyed stabilized liquid developer and method for making
US4524199A (en) * 1983-11-09 1985-06-18 Xerox Corporation Stable polymeric dispersion and methods for making
JP2012098349A (ja) * 2010-10-29 2012-05-24 Kao Corp 液体現像剤の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001888A (en) * 1957-09-25 1961-09-26 Metcalfe Kenneth Archibald Method of developing an electrostatic image
CA692023A (en) * 1964-08-04 M. Oliphant Keith Electrophotographic toners
GB1002061A (en) * 1961-03-13 1965-08-25 Australia Res Lab Improved liquid developer for xerography
GB1020503A (en) * 1960-11-08 1966-02-16 Gevaert Photo Prod Nv Improvements relating to the development of electrostatic charge patterns

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA692023A (en) * 1964-08-04 M. Oliphant Keith Electrophotographic toners
US3001888A (en) * 1957-09-25 1961-09-26 Metcalfe Kenneth Archibald Method of developing an electrostatic image
GB1020503A (en) * 1960-11-08 1966-02-16 Gevaert Photo Prod Nv Improvements relating to the development of electrostatic charge patterns
GB1002061A (en) * 1961-03-13 1965-08-25 Australia Res Lab Improved liquid developer for xerography

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3772053A (en) * 1972-09-22 1973-11-13 Eastman Kodak Co Electrographic formation of dye images
US3885960A (en) * 1972-12-11 1975-05-27 Bell & Howell Co Method of development of liquid electrostatic images using an hydrophobic barrier liquid
US3954640A (en) * 1973-06-27 1976-05-04 Xerox Corporation Electrostatic printing inks
US4097391A (en) * 1975-10-24 1978-06-27 A. B. Dick Company Liquid developer for electrophotographic offset masters
US4476210A (en) * 1983-05-27 1984-10-09 Xerox Corporation Dyed stabilized liquid developer and method for making
US4524199A (en) * 1983-11-09 1985-06-18 Xerox Corporation Stable polymeric dispersion and methods for making
JP2012098349A (ja) * 2010-10-29 2012-05-24 Kao Corp 液体現像剤の製造方法

Also Published As

Publication number Publication date
DE1931129C3 (de) 1974-11-21
DE1931129B2 (de) 1974-04-18
DE1931129A1 (de) 1970-05-27
GB1282892A (en) 1972-07-26
BE734824A (xx) 1969-12-01
NL6909386A (xx) 1969-12-23

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