WO1993002042A1 - Sels d'ammonium quaternaires contenant un amide - Google Patents

Sels d'ammonium quaternaires contenant un amide Download PDF

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Publication number
WO1993002042A1
WO1993002042A1 PCT/US1992/005962 US9205962W WO9302042A1 WO 1993002042 A1 WO1993002042 A1 WO 1993002042A1 US 9205962 W US9205962 W US 9205962W WO 9302042 A1 WO9302042 A1 WO 9302042A1
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WO
WIPO (PCT)
Prior art keywords
salt
toner
alkyl
benzylammonium
quaternary ammonium
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Application number
PCT/US1992/005962
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English (en)
Inventor
John Charles Wilson
Alexandra Dilauro Bermel
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Eastman Kodak Company
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 Eastman Kodak Company filed Critical Eastman Kodak Company
Publication of WO1993002042A1 publication Critical patent/WO1993002042A1/fr

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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
    • G03G9/097—Plasticisers; Charge controlling agents
    • G03G9/09733—Organic compounds
    • G03G9/0975—Organic compounds anionic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • 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
    • G03G9/097—Plasticisers; Charge controlling agents
    • G03G9/09733—Organic compounds
    • G03G9/09741—Organic compounds cationic

Definitions

  • This invention relates to certain new amide- containing quaternary ammonium salts which are useful as charge control agents in dry electrostatographic toners and developers that also serve as adhesion promoters between toner and receiver sheets and as toner fusing temperature reducers.
  • charge control agents are commonly employed to adjust and regulate the triboelectric charging capacity and/or the electrical conductivity characteristics thereof.
  • Many different charge control agents are known which have been incorporated into various binder polymers known for use in toner powders.
  • the need for new and improved toner powders that will perform in new and improved copying equipment has resulted in continuing research and development efforts to discover new and improved charge control agents.
  • This invention provides new amide-containing quaternary ammonium salts having the structure:
  • R ⁇ is C ⁇ -Cg alkyl or aryl
  • R2 and R3 7 which can be the same or different, are alkyl or aryl
  • R4 is _ alkyl
  • R5 is hydrogen or alkyl
  • X is — ⁇ —CH2— r i
  • Z0 is an anion and n is an integer from 2 to
  • the salts of the invention have advantageous utility as charge control agents in dry particulate electrostatographic toner powders.
  • Such toner powders comprise a polymeric matrix phase or polymeric binder which has dispersed therein at least one quaternary ammonium salt having incorporated therein at least one amide moiety that is bonded through an alkylene linking group to a quaternary ammonium nitrogen atom.
  • quaternary ammonium salts When incorporated into toner powders, such quaternary ammonium salts not only function as good charge control agents, but also serve as toner powder fusing temperature depressants and paper adhesion promoters.
  • These salts are preferably dispersed in the polymeric binder matrix phase comprising the core or body portion of a toner particle.
  • Toner powders containing the novel salts of this invention can also be mixed with a carrier vehicle to form electrostatographic developers.
  • Toner powders containing these salts incorporated into the polymeric binder thereof can be used for producing developed toned images on a latently imaged photoconductor element, for transfer of the toned image from the photoconductor element to a receiver sheet and for heat fusion of the toned image on the receiver while employing processes and processing conditions heretofore generally known to the art of electrophotography.
  • particle size as used herein, or the term “size”, or “sized” as employed herein in reference to the term “particles”, means volume weighted diameter as measured by conventional diameter measuring devices, such as a Coulter Multisizer, sold by Coulter, Inc. Mean volume weighted diameter is the sum of the mass of each particle times the diameter of a spherical particle of equal mass- and density, divided by total particle mass.
  • glass transition temperature means the temperature at which a polymer changes from a glassy state to a rubbery state. This temperature (Tg) can be measured by differential thermal analysis as disclosed in “Techniques and Methods of Polymer Evaluation", Vol. 1, Marcel Dekker, Inc., N.Y., 1966.
  • melting temperature or “Tm” as used herein means the temperature at which a polymer changes from a crystalline state to an amorphous state. This temperature (Tm) can be measured by differential thermal analysis as disclosed in "Techniques and Methods of Polymer Evaluation”.
  • adhesion index is a measure of toner adhesion to paper after the toner has been fused.
  • the adhesion index test involves adhering a metal block to a toner patch and measuring the energy required to cause interfacial failure between the toner layer and its contacting substrate by collision of a pendulum with the metal block.
  • the range of adhesion index is from 0 units (no adhesion of toner to substrate) to 100 units (excellent adhesion of toner to substrate) .
  • This invention is directed to amide- containing quaternary ammonium salts of the formula:
  • R ⁇ is C ⁇ -Cg alkyl or aryl
  • R2 and R3 which can be the same or different, are alkyl or aryl
  • R4 is alkyl, aryl or aralkyl
  • R5 is hydrogen or alkyl
  • X is —(—CH2— r > Z ⁇ is an anion and n is an integer from 2 to
  • alkyl includes straight and branched chain alkyl groups and cycloalkyl groups.
  • anion refers to negative ions such as m-nitrobenzenesulfonate, tosylate, tetraphenylborate, dicyanamide, chloride, and the like.
  • aryl includes phenyl, naphthyl, anthryl, and the like.
  • aralkyl includes benzyl, naphthylmethyl and the like.
  • Alkyl and aryl groups can be unsubstituted or substituted with a variety of substituents such as alkoxy, halo or other groups.
  • substituents such as alkoxy, halo or other groups.
  • amide-containing quaternary ammonium salts useful in the present invention include, for example:
  • a presently preferred salt is an amide- containing quaternary ammonium salt of the invention wherein in the formula set forth above R ⁇ is phenyl, R2 is methyl, R3 is methyl, R4 is benzyl, R5 is hydrogen, n is 2 and 20 is m-nitrobenzenesulfonate.
  • the salts of the present invention can be prepared by any convenient route.
  • One general route is to acylate a N,N-di (loweralkyl)alkylenediamine with an acid chloride to produce the corresponding (N,N- di (loweralkyl)amino)alkyl amide which is subsequently quaternized with a reactive aliphatic halide.
  • the quaternary ammonium salt is converted to the desired salt by a metathesis or ion exchange reaction with a reactive alkali metal arylsulfonate or other acid salt.
  • the acid chloride is benzoyl chloride
  • the N,N-di(loweralkyl)alkylenediamine is N / N-dimethylethylenediamine.
  • the corresponding carboxylic acid can be employed.
  • One convenient and presently preferred procedure for such an amide preparation is to prepare a basic aqueous solution of the N,N-di(lower ⁇ alkyl)alkylenediamine. To this solution is slowly added a solution of the acid chloride in a water immiscible organic solvent, methylene chloride being presently preferred. The addition is preferably accompanied by rapid stirring. The mole ratio of N,N- di(loweralkyl)alkylenediamine to total added acid chloride is preferably about 1:1. The ensuing reaction is exothermic and, after the reaction is complete, stirring is preferably continued for a time period, such as at least about 4.5 hours. * The organic layer is then separated, washed with water and dried, preferably over MgS ⁇ 4 or the like, and concentrated. The product is typically an oil which can be purified by distillation.
  • One convenient and presently preferred procedure for the preparation of the quaternary ammonium salt is to prepare the amide and the quaternizing agent as solutes in the same highly polar solvent, acetonitrile being one presently particularly preferred example.
  • the mole ratio of amide compound to the quaternizing agent is preferably about 1:1.
  • Such a solution is then heated at reflux for a time in the range of from about 15 to 20 hours.
  • the reaction mixture is then concentrated by solvent evaporation to yield an oil or a crystalline solid.
  • the product can be used without further purification for the next step in the synthesis, or the product can be purified by recrystallization, for example, from a ketone, such as 2-butanone, or the like, followed by washing and drying.
  • One convenient and presently preferred procedure for preparation of the quaternary ammonium organic salt from the intermediate halide is to dissolve the ion exchange agent in water and add this solution to a second aqueous solution containing the quaternary ammonium salt intermediate.
  • the mole ratio of such salt to such ion exchange agent should be about 1:1.
  • a precipitate is formed immediately which is in the form of an oil.
  • the oil is water washed (preferably with distilled or deionized water) , and then dissolved in a water immiscible organic solvent, such as methylene chloride, or the like.
  • the water layer is separated, the organic layer is dried over MgS ⁇ 4, or the like, and the product thereby concentrated.
  • toner particles can be regarded as being preferably comprised on a 100 weight percent basis of:
  • thermoplastic polymer (b) about 75 to about 97.5 weight percent of a thermoplastic polymer
  • toner particles The size of the toner particles is believed to be relatively unimportant from the standpoint of the present invention; rather the exact size and size distribution is influenced by the end use application intended. So far as now known, the toner particles can be used in all known electrostatographic copying processes. Typically and illustratively, toner particle sizes range from about 0.5 to about 100 microns, preferably from about 4 to about 35 microns.
  • the properties of the thermoplastic polymers employed as the toner matrix phase materials with the salts of the present invention can vary widely.
  • amorphous toner polymers having a glass transition temperature in the range of about 50 to about 120°C or blends of substantially amorphous polymers with substantially crystalline polymers having a melting temperature in the range of about 65 to about 200°C are utilized in the present invention.
  • such polymers have a number average molecular weight in the range of about 1,000 to about 500,000.
  • the weight average molecular weight can vary, but preferably is in the range of about 2 X 10 ⁇ to about 10 ⁇ .
  • thermoplastic polymers used with the salts of this invention are substantially amorphous.
  • mixtures of polymers can be employed, if desired, such as mixtures of substantially amorphous polymers with substantially crystalline polymers.
  • Presently preferred polymers for use in toner powders are styrene/n-butyl acrylate copolymers.
  • preferred styrene/n-butyl acrylate copolymers have a glass transition temperature (Tg) in the range of about 50 to about 100°C.
  • An optional but preferred starting material for inclusion in such a blend is a colorant (pigment or dye) .
  • a colorant pigment or dye
  • Suitable dyes and pigments are disclosed, for example, in U.S. Reissue Patent No. 31,072, and in U.S. Patent Nos. 4,140,644; 4,416,965; 4,414,152; and 2,229,513.
  • One particularly useful colorant for the toners to be used in black and white electrophotographic copying machines is carbon black.
  • colorants are generally employed in quantities in the range of about 1 to about 30 weight percent on a total toner powder weight basis, and preferably in the range of about 2 to about 15 weight percent.
  • Toner compositions can also contain other additives of the types which have been heretofore employed in toner powders, including leveling agents, surfactants, stabilizers, and the like.
  • the total quantity of such additives can vary. A present preference is to employ not more than about 10 weight percent of such additives on a total toner powder composition weight basis.
  • additives such as the quaternary ammonium salts of the present invention, colorants, or the like
  • a preformed mechanical blend of particulate polymer particles, quaternary ammonium salts, colorants, etc. can be roll milled or extruded at a temperature sufficient to melt blend the polymer or mixture of polymers to achieve a uniformly blended composition. Thereafter, the cooled composition can be ground and classified, if desired, to achieve a desired toner powder size and size distribution.
  • the toner components which preferably are preliminarily placed in a particulate form, are blended together mechanically.
  • a melt blending temperature in the range of about 90 to about 240°C is suitable using a roll mill or extruder.
  • Melt blending times that is, the exposure period for melt blending at elevated temperatures
  • the composition can be stored before being ground. Grinding can be carried out by any convenient procedure. For example, the solid composition can be crushed and then ground using, for example, a fluid energy or jet mill, such as described in U.S. Patent No. 4,089,472. Classification, if employed, can be conventionally accomplished using one or two steps.
  • the polymer in place of melt blending, can be dissolved in a solvent and the additives dissolved and/or dispersed therein. Thereafter, the resulting solution or dispersion can be spray dried to produce particulate toner powders.
  • the toner powders used with the salts of the present invention preferably have .a fusing temperature latitude in the range of about 275 to about 400°F, although toner powders with higher and lower fusing temperatures can be prepared and used.
  • the toner powders characteristically display excellent paper adhesion characteristics.
  • the toner powders have a paper adhesion index value in the range of about 30 to about 100, although toner powders with lower such values can be prepared and used.
  • Paper adhesion index values of such toner powders are characteristically higher than those of toner powders prepared with the same polymer and additives but containing a quaternary ammonium salt not of this invention and are comparable to a toner powder prepared with the same polymer and additives but containing no charge control agent.
  • toners containing the novel salts ' of this invention can be mixed with a carrier vehicle.
  • the carrier vehicles which can be used to form such developer compositions can be selected from a variety of materials. Such materials include carrier core particles and core particles overcoated with a thin layer of film-forming resin.
  • the carrier core materials can comprise conductive, non-conductive, magnetic, or non-magnetic materials.
  • carrier cores can comprise glass beads; crystals of inorganic salts such as aluminum potassium chloride; other salts such as ammonium chloride or sodium nitrate; granular zircon; granular silicon; silicon dioxide; hard resin particles such as poly(methyl methacrylate) ; metallic materials such as iron, steel, nickel, carborundum, cobalt, oxidized iron; or mixtures or alloys of any of the foregoing. See, for example, U.S. Pat Nos. 3,850,663 and 3,970,571.
  • iron particles such as porous iron particles having oxidized surfaces, steel particles, and other "hard” or “soft” ferromagnetic materials such as gamma ferric oxides or ferrites, such as ferrites of barium, strontium, lead, magnesium, or aluminum.
  • the carrier particles can be overcoated with a thin layer of a film-forming resin for the purpose of establishing the correct triboelectric relationship and charge level with the toner employed.
  • suitable resins are the polymers described in U.S. Pat. Nos. 3,547,822;
  • One such purpose can be to aid the developer to meet the electrostatic force requirements mentioned above by shifting the carrier particles to a position in the triboelectric series different from that of the uncoated carrier core material, in order to adjust the degree of triboelectric charging of both the carrier and toner particles.
  • Another purpose can be to reduce the frictional characteristics of the carrier particles in order to improve developer flow properties.
  • Still another purpose can be to reduce the surface hardness of the carrier particles so that they are less likely to break apart during use and less likely to abrade surfaces (e.g., photoconductive element surfaces) that they contact during use.
  • Yet another purpose can be to reduce the tendency of toner material or other developer additives to become undesirably permanently adhered to carrier surfaces during developer use (often referred to as scumming) .
  • a further purpose can be to alter the electrical resistance of the carrier particles.
  • a typical developer composition containing the above-described toner and a carrier vehicle generally comprises from about 1 to about 20 percent by weight of particulate toner particles and from about 80 to about 99 percent by weight carrier particles.
  • the carrier particles are larger than the toner particles.
  • Conventional carrier particles have a particle size on the order of from about 20 to about 1200 microns, preferably 30-300 microns.
  • toners containing salts of the present invention can be used in a single component developer, i.e., with no carrier particles.
  • Toner and developer compositions containing salts of this invention can be used in a variety of ways to develop electrostatic charge patterns or latent images.
  • Such developable charge patterns can be prepared by a number of means and be carried for example, on a light sensitive photoconductive element or a non-light-sensitive dielectric-surface element such as an insulator-coated conductive sheet.
  • One suitable development technique involves cascading the developer composition across the electrostatic charge pattern, while another technique involves applying toner particles from a magnetic brush. This latter technique involves the use of a magnetically attractable carrier vehicle in forming the developer composition. After imagewise deposition of the toner particles, the image can be fixed, e.g., by heating the toner to cause it to fuse to the substrate carrying the toner.
  • the unfused image can be transferred to a receiver such as a blank sheet of copy paper and then fused to form a permanent image.
  • a receiver such as a blank sheet of copy paper
  • the invention is further illustrated by the following Examples. In these Examples, all melting points and boiling points are uncorrected. NMR (nuclear magnetic resonance) spectra were obtained with a Varian Gemini-200 NMR spectrometer. All elemental analyses were performed by combustion. Unless otherwise indicated, all starting-chemicals were commercially obtained.
  • Example 3 Preparation of N.N-Dimethvl-N- (2- benzovlaminoethvl)benzylammonium m-Nitrobenzenesulfonate A solution of 11.26 grams (0.05 mol) of sodium m-nitrobenzenesulfonate in 50 milliters of water was added to a solution of 15.94 grams (0.05 mol) of the N,N-dimethyl-N-(2-benzoyla inoethyl)benzylammonium chloride, prepared as described in Example 2, in 50 milliters of water. An oily precipitate formed.
  • the water layer was decanted and the oil was rinsed with water, dissolved in methylene chloride, dried over magnesium sulfate and concentrated to a viscous oil.
  • the oil crystallized and the solid formed was collected and recrystallized from isopropanol.
  • a styrene/n-butyl acrylate copolymer was obtained by limited coalescence polymerization and blended with the additive components identified in the following Table I in the amounts set forth therein.
  • the carbon black was "RegalTM 300". Each blend was roll milled at 150°C for 20 minutes, cooled, crushed and classified to produce a toner powder product having a size of about 12 microns and a size distribution of about 2-30 microns.
  • the charge control agent identified in Table I above as N-octadecyl-N,N- dimethylbenzylammonium m-nitrobenzenesulfonate was utilized for comparative purposes.
  • styrene/n-butyl acrylate toner powder Blends A, B and C were evaluated on a fusing breadboard consisting of a fusing ' roller coated with 100 mils of red rubber, engaged at constant speed and pressure onto a backup roller coated with polytetrafluoroethylene (available commercially as Silverstone ⁇ IM from E.I. duPont de Nemours and Co.) Both roller surfaces were coated by hand with a release oil (60,000 centistoke polydimethylsiloxane oil available from Dow Corning Co.) . The nip width between the two rollers was 0.215-0.240 inch and the fuser was operated at 12.25 inches/second. The fusing temperature was 350°F.
  • the adhesion index values are the average of 8 measurements and the standard deviations are less than 7 units for the measurements.
  • the toner containing the ammonium salt with the amide moiety had a significantly higher adhesion index than the toner containing the N- octadecyl-N,N-dimethyIbenzylammonium m-nitrobenzene ⁇ sulfonate charge control agent, the comparative charge control agent outside the -scope of the invention, and had a comparable adhesion index to the toner without a charge control agent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Developing Agents For Electrophotography (AREA)

Abstract

L'invention décrit de nouveaux sels d'ammonium quaternaires contenant un amide et présentant une efficacité en tant qu'agents de régulation de charge dans des toners et des révélateurs électrostatographiques. Lesdits sels possèdent la structure (I) dans laquelle R1 représente C1-C6 alkyle ou aryle, R2 et R3, qui peuvent être similaires ou différents, représentent alkyle ou aryle, R4 représente alkyle, aryle ou aralkyle, R5 représente hydrogène ou alkyle, X représente (a), Z- représente un anion et n est un entier situé entre 2 et 6. Ces sels d'ammonium quaternaires contenant un amide permettent également aux particules de toners qui les contiennent de présenter des températures de fusion plus basses, ainsi que des indices d'adhésion au papier améliorés.
PCT/US1992/005962 1991-07-18 1992-07-16 Sels d'ammonium quaternaires contenant un amide WO1993002042A1 (fr)

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US73435191A 1991-07-18 1991-07-18
US734,351 1991-07-18

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020231648A1 (fr) * 2019-05-10 2020-11-19 E Ink Corporation Agents de contrôle de charge et dispersions de particules comprenant ceux-ci

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US2459062A (en) * 1944-02-08 1949-01-11 American Cyanamid Co Quaternary ammonium compounds
DE1107671B (de) * 1958-02-11 1961-05-31 Sandoz Ag Verfahren zur Herstellung von quaternaeren 1, 3-Propylendiaminderivaten
US3401119A (en) * 1965-02-16 1968-09-10 Emery Industries Inc Quaternary ammonium compounds and process of making
GB1363299A (en) * 1970-11-26 1974-08-14 Basf Ag Process for the production of quaternary ammonium compounds and novel quaternary ammonium compounds
DE2641286A1 (de) * 1975-11-12 1977-06-02 Texaco Development Corp Quartaere ammoniumverbindung und ihre verwendung
EP0149116A2 (fr) * 1983-12-20 1985-07-24 Bayer Ag Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur
JPS61267059A (ja) * 1985-05-21 1986-11-26 Hodogaya Chem Co Ltd 電子写真用トナ−
JPH02163757A (ja) * 1988-12-19 1990-06-25 Ricoh Co Ltd 静電荷像現像用トナー
DE4040468A1 (de) * 1989-12-28 1991-07-04 Hoechst Ag Biskationische saeureamid- und -imidderivate als ladungssteuermittel

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Publication number Priority date Publication date Assignee Title
US2459062A (en) * 1944-02-08 1949-01-11 American Cyanamid Co Quaternary ammonium compounds
DE1107671B (de) * 1958-02-11 1961-05-31 Sandoz Ag Verfahren zur Herstellung von quaternaeren 1, 3-Propylendiaminderivaten
US3401119A (en) * 1965-02-16 1968-09-10 Emery Industries Inc Quaternary ammonium compounds and process of making
GB1363299A (en) * 1970-11-26 1974-08-14 Basf Ag Process for the production of quaternary ammonium compounds and novel quaternary ammonium compounds
DE2641286A1 (de) * 1975-11-12 1977-06-02 Texaco Development Corp Quartaere ammoniumverbindung und ihre verwendung
EP0149116A2 (fr) * 1983-12-20 1985-07-24 Bayer Ag Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur
JPS61267059A (ja) * 1985-05-21 1986-11-26 Hodogaya Chem Co Ltd 電子写真用トナ−
JPH02163757A (ja) * 1988-12-19 1990-06-25 Ricoh Co Ltd 静電荷像現像用トナー
DE4040468A1 (de) * 1989-12-28 1991-07-04 Hoechst Ag Biskationische saeureamid- und -imidderivate als ladungssteuermittel

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Title
CHEMICAL ABSTRACTS, vol. 108, no. 7, 15 February 1988, Columbus, Ohio, US; abstract no. 52658p, page 408 ; *
CHEMICAL ABSTRACTS, vol. 81, no. 21, 25 November 1974, Columbus, Ohio, US; abstract no. 130791s, page 8 ; *
PATENT ABSTRACTS OF JAPAN vol. 87, no. 416 (P-568)1986 & JP,A,61 267 059 ( HODOGAYA CHEM. CO. LTD. ) *
PATENT ABSTRACTS OF JAPAN vol. 90, no. 912 (P-1104)1990 & JP,A,02 163 757 ( RICOH CO. LTD. ) *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020231648A1 (fr) * 2019-05-10 2020-11-19 E Ink Corporation Agents de contrôle de charge et dispersions de particules comprenant ceux-ci
KR20210128510A (ko) * 2019-05-10 2021-10-26 이 잉크 코포레이션 전하 조절제 및 이를 포함하는 입자 분산액
JP2022529368A (ja) * 2019-05-10 2022-06-21 イー インク コーポレイション 電荷制御剤および電荷制御剤を含む粒子分散物
JP7300006B2 (ja) 2019-05-10 2023-06-28 イー インク コーポレイション 電荷制御剤および電荷制御剤を含む粒子分散物
KR102660154B1 (ko) * 2019-05-10 2024-04-23 이 잉크 코포레이션 전하 조절제 및 이를 포함하는 입자 분산액

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