US3720619A - Liquid developer for electrophotography containing the reaction product of a dyestuff and a fatty acid - Google Patents

Liquid developer for electrophotography containing the reaction product of a dyestuff and a fatty acid Download PDF

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Publication number
US3720619A
US3720619A US00885626A US3720619DA US3720619A US 3720619 A US3720619 A US 3720619A US 00885626 A US00885626 A US 00885626A US 3720619D A US3720619D A US 3720619DA US 3720619 A US3720619 A US 3720619A
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Prior art keywords
dyestuff
fatty acid
liquid
base
salt
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US00885626A
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English (en)
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E Inoue
Y Ueda
T Aizawa
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Kyocera Mita Industrial Co Ltd
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Mita Industrial Co Ltd
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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
    • G03G9/122—Developers with toner particles in liquid developer mixtures characterised by the colouring agents

Definitions

  • a liquid developer for electrophotography which comprises a dispersion of a salt-forming reaction product between at least one dyestuff or dyestulf base containing amino groups and at least one fatty acid of not less than 8 carbon atoms, in a high electric resistance liquid as carrier, said fatty acid being soluble in said carrier liquid; characterized in that a salt formed from said fatty acid and said dyestuff or dyestulf base is insoluble in said high electric resistance liquid, and that said fatty acid is present in an amount of at least 4 mols per mol of said dyestuff or dyestuti base, the amount of said fatty acid being sufficient to disperse said salt in the fine divided state stably in the carrier liquid but being not so excessive as to cause any bleeding of an image to be formed.
  • This invention relates to a liquid developer for electrophotography which comprises a dispersion of a salt-forming reaction product between a dyestutf or dyestulf base containing amino groups and a fatty acid of not less than 8 carbon atoms, in a high electric resistance liquid as carrier. More particularly, the invention relates to such liquid developer for electrophotography, in which the mol ratios of the dyestuif or dyestuif base to the fatty acid within a specific range are employed to improve the dispersibility and stability of the liquid developer, and to form distinct images of good fixing property.
  • Methods of developing electrostatic latent images in electrophotography can be classified into two large categories of dry developing such as cascade development method, magnetic brush development method and powder cloud development method using dry coloring agent powder, and liquid developing using developers comprising a dispersion of coloring material such as pigment in a high electric resistance liquid.
  • This invention belongs to the category of the latter liquid developing.
  • a high electric resistance liquid which is an organic liquid, such as various hydrocarbons, carbon tetrachloride, and ordinary insulating oil,
  • Japanese Pat. No. 273,198 Japanese Pat. No. 273,198 (Japanese Ofiicial Patent Gazette, Publication No. 13,424/60) teaches the developer formed by dispersing a pigment in a high electric resistance liquid, said pigment being coated with such a substance as alkyd resin, linseed oil, synthetic rubber, polystyrene, wax rubber, or the like which are referred to as a control agent, in order to make the pigment electrically selective to the charge of latent images.
  • a control agent such a substance as alkyd resin, linseed oil, synthetic rubber, polystyrene, wax rubber, or the like which are referred to as a control agent, in order to make the pigment electrically selective to the charge of latent images.
  • additives which are excellent as dispersing agents of coloring material gradually deteriorate the electrical insulating property of the carrier liquid, and cause the charge of particulate coloring material to disappear gradually.
  • the additives to reinforce fixing property often precipitate as the result of oxidation, polymerization, gelation, etc.
  • the control agent to coat the pigment particles not only gradually loses its controlling activity as dissolved in the carrier liquid or separated from the pigment particles, but also induces aggregation and precipitation of pigment particles, making the formed images very obscure.
  • liquid developers may possess excellent dispersibility and distinct image-forming abilityv immediately after their preparation, but are subject to a fatal defect in practical use that they lack storage stability and they lose reproducibility of images with the lapse of time.
  • an object of the present invention is to provide a liquid developer for electrophotography which exhibits excellent storage stability during storage and reproducibility of image formation over prolonged period, and which can form distinct images with high fixing property.
  • Another object of the invention is to provide a liquid developer for electrophotography in which the coloring material dispersed in the carrier liquid itself possesses excellent fixing ability and uniform charging characteristic.
  • a liquid developer for electrophotography which comprises a dispersion of a salt-forming reaction product between at least one dyestutf or dyestuif base containing amino groups and at least one fatty acid of not less than 8 carbon atoms, in a high electric resistance liquid as the carrier, said fatty acid being soluble in said carrier liquid, characterized in that a salt formed from said dyestuff or dyestuif base and said fatty acid is soluble in said high electric resistance liquid and that said fatty acid is present in an amount of at least 4 mols per mol of said dyestuff or dyestuff base, the amount of said fatty acid being suflicient to disperse said salt in the finely divided state stably in the carrier liquid but being not so excessive as to cause any bleeding of an image to be formed.
  • salt is intended to mean a kind of a fatty acid salt formed by combining of the dyestuff or dyestuff base containing amino groups which is a base, with the fatty acid which provides acid radicals.
  • salt-forming reaction product means a reaction product mixture formed upon reacting the dyestuff or dyestuff base containing amino groups with the fatty acid in order to make the above-specified salt.
  • Any fatty acid can be used in the present invention as long as it is soluble in the high electric resistance liquid employed, and contains at least 8 carbon atoms, although fatty acid of 10-30 carbon atoms are preferred for obtaining good dispersion stability of the salt of said acid with the dyestutf or dyestuff base in the carrier liquid.
  • saturated fatty acids such as capric, lauric, myristic, palmitic, stearic, and arachidic acids
  • unsaturated fatty acids such as oleic, zoomaric, linoleic, linolenic, eleostearic, moroctic, clupanodonic, nisinic, and ricinoleic acids
  • hydrogenated oils of the foregoing acids may be used. It is of course permissible to use mixtures of those fatty acids.
  • fatty acid mixtures obtained through hydrolysis of natural fat and oil such as animal and vegetable oils may be used.
  • the fatty acid employed is soluble in the high electric resistance liquid.
  • liquid developers of excellent dispersion stability cannot be formed.
  • oleic acid is soluble in almost all liquid hydrocarbons, including even isoparaflin-type hydrocarbons having low dissolving power.
  • stearic acid is also soluble in isoparafiin-type hydrocarbons in summer, but the solubility is considerably reduced in Winter, while it will be soluble to an appreciable degree in aromatic hydrocarbons or mixtures of aromatic hydrocarbons with aliphatic hydrocarbons.
  • Fatty acids which exhibit broad adaptability to various liquid hydrocarbons and seasons and consequently are preferred for the purpose of this invention are unsaturated fatty acids, particularly oleic acid.
  • the salt-forming reaction product of such fatty acid with a dyestuff or dyestulf base containing amino groups is dispersed in a high electric resistance liquid.
  • the salt of the fatty acid with the dyestuff or dyestuif base must be insoluble in the high electric resistance liquid. If the salt is soluble in said liquid, distinct images cannot be formed.
  • the quantity of the fatty acid should be at least 4 mols per mol of the dyestuff or dyestulf base, being sufiicient to finely divide and disperse said salt in the liquid but not so much as to cause the bleeding of an image to be formed, for achieving the intended improvements in the developers storage stability, distinctness and fixing property of images, and in the reproducibility of image formation over prolonged period.
  • R denotes a long chain alkyl or alkenyl group of at least 7 carbon atoms, preferably 9-29 carbon atoms,
  • D is the dyestuff residue
  • each of R and R is hydrogen or a dyestulf residue
  • n is an integer of not less than 1.
  • the salt of the dyestuff or dyestuff base with the fatty acid is simply dispersed in the carrier liquid, the salt is dissociated into the fatty acid and the dyestuff or dyestulf base, and because the dyestuff or dyestutf base generally lacks dispersibility in the carrier liquid, uniform charging ability, and fixing property, the storage stability and image-reproducibility over prolonged period of the liquid developer tend to be deteriorated.
  • the dispersing step of the saltforming reaction product between the dyestuff or dyestutf base containing amino groups and the fatty acid in a high electric resistance liquid if the fatty acid is caused to be present in an amount of at least 4 moles per mole of the dyestuff or dyestutf base and furthermore excessive within a specific range depending on the type of dyestuff or dyestuff base and the type of fatty acid, the mobility of equilibrium to the right, i.e., the tendency of freeing the dyestutf or dyestuff base, is inhibited, and the salt dispersed in the liquid is stabilized.
  • the salt of a dyestutf or dyestuff base with a fatty acid normally very easily dissolves and disperses in excessive fatty acid, to form as a whole a homogeneous solution or solid solution.
  • the salt of the dyestulf or dyestutf base with a fatty acid is not only maintained in the solution or solid solution with high stability, but when the solution or solid solution is dispersed in a high electric resistance liquid which is a non-solvent, with optional intervening heating, it is made possible to disperse the imageforming material as fine particles, with high stability than any that can be obtained with mechanical stirring or shearing. In that case, if the excessive fatty acid is dissolved in the high electric resistance liquid, it will probably contribute to the stability of the salt of the dyestuff or dyestulf base and the fatty acid, as illustrated by the foregoing formula of equilibrium.
  • the salt-forming reaction product between a dyestulf or dyestutf base and a fatty acid which is the image-forming material is self-stabilized by the action of chemical equilibrium of itself or that of chemical equilibrium of the dyestuff or dyestuff base and the fatty acid and, furthermore, since the salt-forming reaction product is homogeneous, the liquid developer is completely free of the defects inherent in the conventional liquid developers in which the pigment particles are simply mechanically coated with a control agent, such as poor storage stability and image-reproducibility over prolonged period.
  • the fatty acid it is necessary to make the fatty acid present in an amount of at least 4 mols per mol of the dyestuff or dyestuff base which is not yet converted to the salt, the amount furthermore being sufficient to disperse the salt or salt-forming reaction product between the fatty acid and the dyestuff or dyestuff base in the finely divided state stably in a high electric resistance liquid.
  • the lower limit in the amount of the fatty acid meeting the above requirement differs depending on the type of the dyestuff or dyestuff base, and the type of the fatty acid, but generally is within the range of 41,000 mols per mol of the dyestuff or d'yestuff base.
  • the suitable amount for individual case can be easily determined by simple experiments.
  • the upper limit in the amount of the fatty acid is determined as such which will not yield the formed images fluid.
  • Such an amount is rather variable depending on such factors as the type of the dyestuff or dyestuff base, type of the fatty acid, and fatty acid concentration in the dispersion liquid, but can be easily determined for each individual case by simple experiments, within the aforesaid range of 4-1,000 mols per mol of the dyestuff or dyestuff base.
  • the fatty acid is oleic acid
  • stearic acid it is preferable to make it present in an amount of 4 to 40 mols per mole of the dyestuff or dyestuff base.
  • linoleic acid is used as the fatty acid
  • a preferable amount is 10 to 200 mols per mol of the dyestuff or dyestuff base.
  • a preferable amount is within a range of from 40 to 200 mols per mol of the dyestuff or dyestuff base.
  • the fatty acid is lauric acid
  • a preferable amount ranges from 10 to 100 mols per mol of the dyestuff or dyestuff base.
  • the type of the dyestuff or dyestuff base to be employed for producing the salt-forming reaction product in accordance with the invention is not critical, as long as it contains amino groups which can form a salt with a fatty acid, and the salt or salt-forming reaction product is insoluble in the high electric resistance liquid.
  • Examples of such dyestuff or dyestuif base include those possessing amino groups capable of forming a salt with a fatty acid, selected from basic azo dyes, basic diphenylmethane dyes, basic triphenylmethane dyes, acridine dyes, pyronine dyes, Rhodamine dyes, quinoneimine dyes, azo-type disperse dyes, and anthraquinone dyes.
  • Such dyestuff or dyestuff base can be used singly or in combination.
  • Visible image of desired color tone can be obtained by combined use of more than one dyestuffs or dyestuff bases of different color tones, or further varying the quantitative ratios of such plural dyestuffs or dyestuff bases.
  • the image-forming material of this invention is extremely homogeneous as particles themselves as well as in interrelations of the particles, the developer never causes uneven coloring due to nonuniform electrodeposition rates and charges among the particles, nor change in color tone occurring with the developer deterioration with time passage, unlike the conventional mere mixtures of dyestuffs or pigment particles, or other particulate coloring material.
  • useful dyestuffs and dyestuff bases include the following:
  • BASIC AZO DY ES 0 Chrysoidine Base [C.”I. solvent orange 3 (11270B)] o Bismarck Brown G Base [C.I. basic brown 1 (21000)] (2) BASIC DIPHENYLMETHANE DYES o Auramine [C.I. basic yellow 2 (41000)] Auramine Base [C.I. solvent yellow 34 (41000 B)] (3) BASIC TRIPHENYLMETHANE DYES (4) ACRIDINE DYES Acridine [C.I. basic orange 14 (46005)] Pheonine AL [C.I. basic dye (46055 (5) PYRONINES o Pyronine G [C.I.
  • the high electric resistance liquid used as the dispersion medium can be any organic liquid which dissolves the fatty acid specified in the foregoing, but does not dissolve the salt or salt-forming reaction product between the fatty acid and the dyestuff or dyestuff base, and which has an electric resistance of at least 10 t2-cm., preferably not less than 10* tl-cm.
  • straight or branched chain aliphatic hydrocarbons such as n-hexane, n-octane and isoparaffin; alicyclic hydrocarbons such as cyclohexane terpenes; aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as trichloroethane, methylene chloride and fluoroinated hydrocarbon; and silicones such as dialkyl and diphenyl siloxanes
  • solvents for example, mixed hydrocarbons of naphtha, kerosene and the like.
  • use of liquid hydrocarbons, particularly isoparaflin type hydrocarbons is preferred.
  • the liquid developer of the invention can be prepared by the following procedures.
  • a fatty acid or fatty acid mixture and a dyestuif or dyestutf base are heated in the optional presence of a suitable solvent, to form a salt of the fatty acid with the dyestuff or dyestuff base.
  • the amount of the fatty acid to the dyestuff or dyestuif base should be within the afore-specified range.
  • a suitable amount of oleic acid is 4-800 mols per mol of the base, preferably -200 mols.
  • the salt-forming reaction of the fatty acid with the dyestuff or dyestutf base is performable at room temperature, but it is preferred to employ elevated temperatures of 50150 C. in order to sufficiently complete the reaction. If side reaction or reactions other than the salt formation take place to a slight degree, such is not appreciably detrimental to the results of this invention.
  • the completion of the salt-forming reaction can be normally confirmed by color change in the reaction mixture.
  • the salt-forming reaction product in this stage can be normally obtained in the state ranging from homogeneous solution to highly viscous, semi-solid, or fully solid solution.
  • the salt-forming reaction product in solution to solid solution form is added to the high electric resistance liquid described in the foregoing, to be finely divided and dispersed in the latter, if necessary, with the aid of ultrasonic waves or high shearing force agitation.
  • the saltforming reaction product may be used at the concentrations useful for developing electrostatic latent images, that is, the concentrations of 0.005 to 0.3 wt. percent based on the carrier liquid, or may be used at concentrations as high as 30 wt. percent or even higher, so that the product may be diluted with the carrier liquid immediately before actual use.
  • the liquid developers of the invention may also be prepared by the steps of forming the salt using the fatty acid in an amount less than the desired, for example, in stoichiometric amount required for the salt formation, adding to the resulting salt forming reaction product the remaining amount of fatty acid to form a homogeneous solution, and dispersing the solution in the carrier liquid.
  • a hydrochloride of the dyestuff or dyestufi base may be reacted with an alkali metal salt of the fatty acid, i.e., soap, at stoichiometric amounts, and the resulting fatty acid salt may be refined and dissolved in the fatty acid, followed by dispersing of the solution in a carrier liquid.
  • an alkali metal salt of the fatty acid i.e., soap
  • the salt or salt-forming reaction product between the fatty acid and the dyestufi or dyestuff base which is the image-forming material is stably maintained in the form of fine particles in the carrier liquid by the action of chemical equilibrium caused by excessive fatty acid, and the dispersion stability is not impaired after a long period storage.
  • the image-forming material in the liquid developer of the invention is itself homogeneous, and never alters or causes charge variation during storage.
  • the image-forming material in the liquid developer of the invention i.e., the salt or salt-forming reaction product between the fatty acid and the dyestutf or dyestulf base, itself possesses fixing onto sensitive layer.
  • the invention successfully provides a liquid developer for electrophotography exhibiting excellent storage stability, distinctness and fixing property of images, and image-reproducibility over prolonged periods.
  • Nigrosine Base The structural formula of Nigrosine Base is currently unestablished. Therefore its molecular weight was calculated from a presumed structural formula, and the weight ratios to realize the 1:1 mol ratio of Nigrosine Base and the fatty acids were determined as follows:
  • Amount of fatty acid to 1 gram of Nigrosine Base G. Capric acid 0.33 Stearic acid 0.54 Oleic acid 0.53 Linoleic acid 0.53
  • the amount of the fatty acid was calculated as the multiple of the aboveindicated amount of the specific acid employed.
  • Each sample was prepared by taking the Nigrosine Base and fatty acid of the amounts accurately weighed into a beaker, and reacting them under stirring while heating in an oil bath.
  • the mol ratio of Nigrosine Base to the fatty acid was 1:1, 1:2, and 1:4, a minor amount of benzene was added to the system because the amount of the fatty acid was relatively too small to dissolve the Nigrosine Base. After the reaction under heating, the benzene was thoroughly removed by evaporation.
  • salt-forminig reaction products were each accurately weighed and dispersed in the carrier liquid at the predetermined concentration with the aid of ultrasonic waves. Also for examining the dispersibility of the reaction product in the carrier liquid, and changes in distinctness and fixing property of the images with time passage, the dispersions were allowed to stand in dark place at room temperature for a week.
  • the image is slightly spoiled when rubbed with finger with normal force.
  • o Linoleic acid and oleic acid give liquid developers of good dispersibility under wide variety of conditions.
  • o Stearic acid gives poor results with isoparafiin type hydrocarbon as the carrier, because it is practically insoluble in the latter at room temperature, but gives satisfactory results with Whitesol which contains aromatic hydrocarbon.
  • EXAMPLE 3 One hundred (100) g. of palmitic acid was heated to 70-80 C. to be liquefied, and into which 2 g. of Methyl Violet Base was gradually added with stirring. After the dyestuff base was completely dissolved, the solution was further heated to 100 C. and maintained at said temperature for an hour. The system was allowed to cool off of itself to 20-30 C., to provide a homogeneous, viscous salt-forming reaction product. Five (5) g.
  • EXAMPLE 5 To 16 g. of lauric acid heated and fused at 50-60 C., 1 g. of Nigrosine Base was gradually added under stirring, and further heated for an hour. Separately, 50 cc. of New Sol Delux (product of Nippon Petroleum Co.) as an insulative carrier liquid was maintained at 60 C., and into which 1 g. of the above-obtained salt-forming reaction product was added and completely dissolved. The solution was then added to 950 cc. of same carrier liquid to provide a dispersion containing extremely fine particles without the aid of ultrasonic waves as mentioned in Example 4. This liquid developer was adhered onto negative electrostatic latent images, and formed blackish purple images of high resolving power.
  • New Sol Delux product of Nippon Petroleum Co.
  • EXAMPLE 7 One (1) g. of Diacelliton Fast Brilliant Blue B (a disperse dye, product of Mitsubishi Kasei Kogyo K.K) was added gradually to 30 g. of oleic acid under stirring, to form a homogeneous mixture, which was subsequently heated to 100-120" C. and stirred for 30 minutes to be reacted.
  • Diacelliton Fast Brilliant Blue B a disperse dye, product of Mitsubishi Kasei Kogyo K.K
  • the reaction product was allowed to cool off of itself to approximately 20 C., and the unreacted material which precipitated was removed by filtration.
  • One (1) g. of the reaction product was added to 1 liter of nheptane and lightly stirred, to provide a liquid developer of excellent suspension quality and storage stability containing the finely dispersed particles.
  • the polarity of the particles in the liquid developer as examined by the method similar to that of Example 1 was charged 100% positive. Therefore, the particles were adhered onto negative electrostatic latent images, forming blue images of 13 good fixing property, little edge eifect and high resolving power.
  • EXAMPLE 8 To 60 g. of stearic acid heated to approximately 80 C., 3 g. of Magenta Base, a basic triphenylmethane dyestuff base, was gradually added under stirring, to form a homogeneous and viscous salt-forming reaction product. Two (2) g. of this product was added to 50 cc. of mineral spirit, and heated to 100C. to be dissolved. Upon adding the resulting solution to 950 cc. of mineral spirit under stirring, a liquid developer of excellent suspension quality in which the salt-forming reaction product was dispersed as extremely fine particle was obtained. The polarity of the particles in the liquid developer was examined similarly to the foregoing example, to confirm that it was charged 100% negative. The liquid developer was adhered onto positive electrostatic latent images, and formed pink images of little edge effect and high resolving power. Also from negative electrostatic latent images, reversed images were obtained with this developer.
  • EXAMPLE 9 To 100 g. of linoleic acid, 10 g. of Methylene Blue Base, a quinoneimine dyestulf base, was added under stirring and completely dissolved, followed by heating to 120-150 C. for an hour to efiect the reaction. The system was allowed to cool 01f of itself, to form a homogeneous, viscous salt-forming reaction product. One (1) g. of the product was added to 1 liter of dimethylpolysiloxane and dispersed with ultrasonic waves. Thus a dispersion of fine particles of excellent suspension quality was obtained. The charge of the particles was examined similarly to the foregoing examples, to confirm that the particles were 100% positively electrified. This liquid developer was adhered onto negative electrostatic latent images, and formed blue images of good fixing property, little edge effect and high resolving power.
  • a liquid developer for electrophotography consisting of a dispersion of (A) a salt-forming reaction product of (a) at least one dyestufi or dyestuff base containing amino groups selected from the groups consisting of basic azo dyes, basic diphenyl methane dyes, basic triphenyl methane dyes, acridine dyes, promine dyes, rhodamine dyes, quinoneimine dyes, azo type disperse dyes, anthraquinone dyes, and bases of these dyes, and b) oleic acid in (B) a carrier consisting of (i) a high electric-resistant liquid selected from the groups consisting of liquid hydrocarbons, liquid halogenated hydrocarbons and silicone oils, and (ii) oleic acid dissolved in said high electric-resistant liquid, the total amount of said oleic acid (b) and oleic acid (ii) being from 10 to 400 mols per mol of said dyestut
  • a liquid developer for electro-photography consisting of a dispersion of a salt-forming reaction product of (a) Nigrosine Base (Cl. 50415B), and (b) oleic acid in a carrier consisting of (i) a liquid hydrocarbon, and (ii) oleic acid dissolved in said liqud hydrocarbon, the total amount of said oleic acid (b) and oelic acid (ii) being from 10 to 400 mols per mol of said Nigrosine Base.
  • a liquid developer for electro-photography consisting of a dispersion of a salt-forming reaction product of (a) Victoria Blue Base (C.I. 4045B), and (b) oleic acid in a carrier consisting of (i) a liquid hydrocarbon, and (ii) oleic acid dissolved in said liqud hydrocarbon, the total amount of said oleic acid (b) and oleic acid (ii) being from 10 to 400 mols per mol of said Victoria Blue Base.
  • a carrier consisting of (i) a liquid hydrocarbon, and (ii) oleic acid dissolved in said liqud hydrocarbon, the total amount of said oleic acid (b) and oleic acid (ii) being from 10 to 400 mols per mol of said Victoria Blue Base.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Liquid Developers In Electrophotography (AREA)
US00885626A 1968-12-18 1969-12-16 Liquid developer for electrophotography containing the reaction product of a dyestuff and a fatty acid Expired - Lifetime US3720619A (en)

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JP43092573A JPS5040347B1 (enrdf_load_stackoverflow) 1968-12-18 1968-12-18

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US (1) US3720619A (enrdf_load_stackoverflow)
JP (1) JPS5040347B1 (enrdf_load_stackoverflow)
FR (1) FR2026483A1 (enrdf_load_stackoverflow)
GB (1) GB1282058A (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3793048A (en) * 1968-04-18 1974-02-19 S Nagashima Developing process using toners at a reactor product between a dye having an amino group and organic halide
US3900413A (en) * 1972-06-15 1975-08-19 Commw Of Australia Reactive developer for electrophotography
US3985663A (en) * 1974-03-14 1976-10-12 Xerox Corporation Conductive inks containing quaternary ammonium compounds
US3992311A (en) * 1972-05-15 1976-11-16 Metcalfe Kenneth A Reactive developer for electrophotography
US4059444A (en) * 1974-03-14 1977-11-22 Xerox Corporation Liquid development using conductive inks
US4301227A (en) * 1973-03-29 1981-11-17 Sumitomo Chemical Company, Limited Electrophotographic liquid developer

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3793048A (en) * 1968-04-18 1974-02-19 S Nagashima Developing process using toners at a reactor product between a dye having an amino group and organic halide
US3992311A (en) * 1972-05-15 1976-11-16 Metcalfe Kenneth A Reactive developer for electrophotography
US3900413A (en) * 1972-06-15 1975-08-19 Commw Of Australia Reactive developer for electrophotography
US4301227A (en) * 1973-03-29 1981-11-17 Sumitomo Chemical Company, Limited Electrophotographic liquid developer
US3985663A (en) * 1974-03-14 1976-10-12 Xerox Corporation Conductive inks containing quaternary ammonium compounds
US4059444A (en) * 1974-03-14 1977-11-22 Xerox Corporation Liquid development using conductive inks

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GB1282058A (en) 1972-07-19
DE1963564A1 (de) 1970-07-16
DE1963564B2 (de) 1974-07-04
JPS5040347B1 (enrdf_load_stackoverflow) 1975-12-23
FR2026483A1 (enrdf_load_stackoverflow) 1970-09-18

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