EP1356346A2 - Affichages electrophoretiques contenant des particules modifiees - Google Patents
Affichages electrophoretiques contenant des particules modifieesInfo
- Publication number
- EP1356346A2 EP1356346A2 EP01968713A EP01968713A EP1356346A2 EP 1356346 A2 EP1356346 A2 EP 1356346A2 EP 01968713 A EP01968713 A EP 01968713A EP 01968713 A EP01968713 A EP 01968713A EP 1356346 A2 EP1356346 A2 EP 1356346A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- particles
- groups
- electrodes
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/165—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field
- G02F1/166—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect
- G02F1/167—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field characterised by the electro-optical or magneto-optical effect by electrophoresis
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/165—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on translational movement of particles in a fluid under the influence of an applied field
- G02F1/1675—Constructional details
- G02F2001/1678—Constructional details characterised by the composition or particle type
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/02—Materials and properties organic material
Definitions
- the present invention relates to electrophoretic displays and non-emissive display systems.
- the present invention more particularly, relates to electrophoretic displays and non- emissive display systems, using particles, such as pigments, which improve the display.
- a potential difference can cause the particles to migrate toward one of the electrodes thus forming a display which can be used to form images or text on a display which is located on one of the electrodes since one of the electrodes is transparent.
- the electrophoretic displays form images and text through the use of a potential difference between two electrodes and a quantity of charged particles. If these charged particles agglomerate they would not remain suspended in the dielectric fluid, and the ability to form reusable display of images or text can be greatly diminished if not made problematic. Accordingly, there is a need to improve upon the electrophoretic display technology in order to ensure that clear and visually sharp images can be obtained using electrophoretic display technology and pigment particles.
- a feature of the present invention is to provide electrophoretic displays which provide sharp and clear images on the display.
- Another feature of the present invention is to provide an electrophoretic display wherein the suspension of charged particles is maintained and agglomeration of the charged particles is significantly reduced, if not, eliminated.
- Another feature of the present invention is to provide non-emissive display systems which accomplish the above-described benefits.
- the present invention relates to an electrophoretic display having an arrangement of microscopic containers and first and second electrodes disposed on and covering opposite sides of the arrangement. One of the electrodes is substantially visually transparent.
- the electrophoretic display also has means for creating a potential difference between the two electrodes.
- each microscopic container in the electrophoretic display has at least one type of dielectric fluid and a suspension of particles in the dielectric fluid.
- the fluid and the particles are contrasting visually.
- the particles for purposes of the present invention have attached at least one organic group, wherein the organic group contains an ionic and/or ionizable group and wherein the organic group on the particles causes the particles to migrate towards one of the electrodes when there is a potential difference created between the two electrodes.
- the present invention further relates to a non-emissive display system which contains a pair of oppositely disposed electrodes and at least one display element located between the electrodes.
- the display element is visually responsive to a potential difference between the two electrodes.
- the non-emissive display system further has a display piezoelectric element connected to the electrodes wherein deformation of the piezoelectric element produces the potential difference.
- the display element in the non-emissive display system contains a substantially two-dimensional arrangement of discrete microscopic containers as described above for the electrophoretic display.
- the particles within the container as stated above, have attached at least one organic group wherein the organic group contains an ionic and/or ionizable group such that the potential difference occurring between the two electrodes causes these particles to migrate toward one of the electrodes.
- the present invention relates to an electrophoretic display and a non-emissive display system.
- the electrophoretic display contains an arrangement of microscopic containers which are preferably discrete.
- the microscopic containers each contain a dielectric fluid and particles which are suspended in the dielectric fluid.
- the fluid and the particles contrast visually so as to have different colors.
- the particles for purposes of the present invention have attached at least one organic group, wherein the organic group includes an ionic and/or ionizable group.
- a first and second electrodes are located on opposite sides of the arrangement of microscopic containers and cover this arrangement on both sides. At least one of the electrodes is substantially visually transparent.
- the electrophoretic display of the present invention includes means for creating a potential difference between the two electrodes such that when there is a potential difference, the particles migrate toward one of the electrodes.
- the present invention further relates to a non-emissive display system which contains an arrangement of discrete microscopic containers as described above which contains the dielectric fluid and the particles suspended within the fluid. These elements comprise the display element.
- the non-emissive display system further includes at least two electrodes wherein the display element is located between the two electrodes and the display element is visually responsive to a potential difference between the electrodes.
- the non- emissive display system contains a display piezoelectric element connected to the electrodes wherein deformation of the piezoelectric element produces a potential difference which causes the particles to migrate toward one of the electrodes.
- Another embodiment of the present invention relates to a rewritable display media in which an optical response results from the movement of particles in an electric field, wherein the particles have attached at least one organic group having at least one ionic group or ionizable group or both.
- the electrode for purposes of the present invention can be any conventional electrode which satisfies the needs of the electrophoretic display.
- the electrode can be a semiconductor which is located on a substrate such as glass, mylar, and the like.
- Such electrodes as described in U.S. Patent Nos. 3,668,106 and 4,305,807 can be used for purposes of the present invention.
- a driver circuit for instance, can be electrically connected to the electrodes which is capable of creating a potential difference between the electrodes to cause migration of the particles to one or to the other electrode within the desired switching time.
- these containers each contain a dielectric fluid and particles which are suspended within the dielectric fluid.
- the microscopic containers or microcapsules can be any shape, spherical or non-spherical but are preferably spherical or of a similar round shape.
- the dimensions can vary and are preferably from about 5 to about 500 microns, and more preferably from about 25 to 250 microns.
- the walls of the microscopic containers preferably exhibit resistivity to the dielectric fluid.
- the dielectric fluid or liquid can be any dielectric fluid as long as it is compatible with the particles present in the container.
- the dielectric fluid is a hydrophobic liquid.
- the hydrophobic liquid is generally chosen based on viscosity, dielectric constant, charge, and density.
- Dielectric fluids that can be used, include, but are not limited to, darkly colored hydrophobic fluids, such as isoparaffinic petroleum solvent or trichlorotrifluoroethane, or mixtures thereof.
- halogenated hydrocarbons can also be used and the dielectric liquid can also include dyes or other coloring agents (e.g., electrically neutral pigments) to create the desired color of the dielectric fluid.
- the dielectric fluid can also be, for purposes of the present invention, an electrophoretic fluid which may include one or more fluids.
- the particles are particles having at least one organic group attached to the particles.
- the particle is a pigment particle.
- the pigment can be any wide range of colors.
- the particles can be any size such as from about 100 microns or more to less than one micron and preferably have a size range of from about 0.05 microns to about 25 microns.
- the displays of the present invention comprise particles having an attached organic group. The choice of organic groups is dependent on both the dielectric fluid and the capsule material. The organic group should enable the particles to be dispersible in the dielectric fluid but not interact with the capsule.
- the choice of organic group as well as the amount attached must be made carefully in order for the display to function properly.
- the particles were treated or coated with charge-control agents which may have been adsorb directly onto the particle.
- the present invention attaches at least one type of organic group on the particles, wherein this attachment is preferably a chemical attachment or covalent bond.
- Such an attachment provides great stability to the organic group remaining with the particle and not becoming disassociated in the dielectric liquid.
- a major fall back of previous electrophoretic displays is the lack of ability to maintain a consistent charge or chargeable particle due to the instability of the charge-control agent being merely coated or adsorbed onto the particle.
- the electrophoretic display After all, if the charge-control agent is susceptible to being removed from the particle, the electrophoretic display will operate at less than optimum efficiency and could possibly not work at all if a sufficient amount of the charge control agent does not remain on the particles.
- the present invention uses particles, and preferably pigments, having attached at least one type of organic group. The use of such modified particles have several advantages from previous electrophoretic displays.
- a suspension or coacervation type polymerization which causes the encapsulation of the dielectric liquid and the particles.
- the present invention makes this quite possible since the particles of the present invention which have attached organic groups having at least one ionic and/or ionizable group are substantially and uniformly suspended in a dielectric fluid which can be hydrophobic, for instance, without the need of suspension aids and the like. Accordingly, the present invention enables a uniform distribution of particles in dielectric fluids in the formation of the microscopic containers and further leads to maintaining this suspension throughout the use of the electrophoretic display. Thus, the problems of agglomeration can be significantly avoided.
- the arrangement can be any shape, such as flat or curved and typically is a two- dimensional arrangement which has various thicknesses.
- the arrangement can be accomplished by packing the microcontainers against one another in an array or dispersing the microscopic containers in a transparent matrix and the like.
- Various microencapsulation techniques can be used to create the microscopic containers including those described for instance, in U.S. Patent Nos. 4,001,140; 4,273,672; and 3,585,381, all incorporated in their entirety by reference herein.
- the display that is used in the present invention can be any conventional display used 5 to display images such as those used in liquid-crystal displays.
- the microscopic containers for instance, can be inserted into a cell housing the two electrodes.
- the microscopic containers can also be applied into a display by any various means known to those skilled in the art involving the insertion of microcapsules on a substrate.
- the display can be arranged in any number of designs including unitary displays, continuous displays, and the like. l o
- the non-emissive display system essentially involves the same components described above wherein the non-emissive display system involves two electrodes wherein a display element is located between the electrodes.
- the display element contains the arrangement of microscopic containers as described above wherein the containers contain a dielectric fluid and the modified particles.
- the display element is visually responsive to a potential
- the non-emissive display system further involves a display piezoelectric element which is connected to the electrodes wherein deformation of this piezoelectric element produces the potential difference which causes the particles in the microscopic containers to migrate to one of the electrodes.
- the display piezoelectric element can be any conventional element known to those skilled in the art such as those described in
- the pigment can be, but is not limited to, pigments traditionally used in ink compositions (including inkjet ink compositions), coating compositions (including paint formulations), liquid and solid toners, films, plastics, rubbers, and the like. Examples include, but are not limited to, black pigmentsJe.g., carbon products like carbon black) and
- the desired colored pigment may be chosen from a wide range of conventional colored pigments.
- the pigment product can be any carbon product capable of reacting with a diazonium salt to form the modified pigment product.
- the carbon may be of the crystalline
- Examples include, but are not limited to, graphite, carbon black, vitreous carbon, activated charcoal, activated carbon, carbon fibers, and mixtures thereof. Finely divided forms of the above are preferred. It is also possible to utilize mixtures of different pigment products.
- the colored pigment can be blue, black, brown, cyan, green, white, violet, magenta, red, yellow, as well as mixtures thereof.
- Suitable classes of colored pigments include, for example, carbon black, carbon products, anthraquinones, phthalocyanine blues, phthalocyanine greens, diazos, monoazos, pyranthrones, perylenes, heterocyclic yellows, quinacridones, and (thio)indigoids.
- Representative examples of phthalocyanine blues include copper phthalocyanine blue and derivatives thereof (Pigment Blue 15).
- quinacridones include Pigment Orange 48, Pigment Orange 49, Pigment Red 122, Pigment Red 192, Pigment Red 202, Pigment Red 206, Pigment Red 207, Pigment Red 209, Pigment Violet 19 and Pigment Violet 42.
- Representative examples of anthraquinones include Pigment Red 43, Pigment Red 194 (Perinone Red), Pigment Red 216 (Brominated Pyanthrone Red) and Pigment Red 226 (Pyranthrone Red).
- perylenes include Pigment Red 123 (Vermillion), Pigment Red 149 (Scarlet), Pigment Red 179 (Maroon), Pigment Red 190 (Red), Pigment Violet 19, Pigment Red 189 (Yellow Shade Red) and Pigment Red 224.
- thioindigoids include Pigment Red 86, Pigment Red 87, Pigment Red 88, Pigment Red 181, Pigment Red 198, Pigment Violet 36, and Pigment Violet 38.
- Representative examples of heterocyclic yellows include Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 65, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 151, Pigment Yellow 117, Pigment Yellow 128 and Pigment Yellow 138.
- Such pigments are commercially available in either powder or press cake form from a number of sources including, BASF Corporation, Engelhard Corporation and Sun Chemical Corporation. Examples of other suitable colored pigments are described in the Colour Index, 3rd edition (The Society of Dyers and Colourists, 1982). The color pigment will typically have a wide range of BET surface areas, as measured by nitrogen adsorption.
- the carbonaceous material can be an aggregate comprising a carbon phase and a silicon-containing species phase.
- a description of this aggregate as well as means of making this aggregate is described in PCT Publication No. WO 96/37547 and WO 98/47971 as well as U.S. Patent Nos. 5,830,930; 5,869,550; 5,877,238; 5,919,841 ; 5,948,835; and 5,977,213. All of these patents and publications are hereby incorporated in their entireties herein by reference.
- the carbonaceous material for purposes of the present invention can also be an aggregate comprising a carbon phase and metal-containing species phase where the metal- containing species phase can be a variety of different metals such as magnesium, calcium, titanium, vanadium, cobalt, nickel, zirconium, tin, antimony, chromium, neodymium, lead, tellurium, barium, cesium, iron, molybdenum, aluminum, and zinc, and mixtures thereof.
- the aggregate comprising the carbon phase and a metal-containing species phase is described in U.S. Patent No. 6,017,980, also hereby incorporated in its entirety herein by reference.
- the carbonaceous material includes a silica-coated carbon black, such as that described in U.S. Patent No. 5,916,934 and PCT Publication No. WO 96/37547, published November 28, 1996, also hereby incorporated in their entirety herein by reference.
- the particle size distribution is based on the mean volume diameter of the pigment particles as measured by the dynamic light scattering method.
- the particle size distribution range of the colored pigments of the present invention is from about 10 nm to about 300 nm, and preferably is from about 10 nm to about 200 nm, more preferably is from about 20 nm to about 150 nm, and most preferably is from about 50 nm to about 100 nm.
- the modified particle is preferably a colored pigment having attached at least one organic group.
- the organic group preferably contains a) at least one aromatic group, at least one Ci-Cioo alkyl group, or mixtures thereof; and further contains b) at least one ionic group, ionizable group, or mixtures thereof.
- At least one aromatic group includes, but is not limited to, unsaturated cyclic hydrocarbons containing one or more rings and may be substituted or unsubstituted, for example with alkyl groups.
- Aromatic groups include aryl groups (for example, phenyl, naphthyl, anthracenyl, and the like) and heteroaryl groups (for example, imidazolyl, pyrazolyl, pyridinyl, thienyl, thiazolyl, furyl, triazinyl, indolyl, and the like).
- At least one Ci- Cioo alkyl group may be branched or unbranched, substituted or unsubstituted.
- An ionizable group is one capable of forming an ionic group in the medium of use.
- the ionic group may be an anionic group or a cationic group and the ionizable group may form an anion or cation.
- Ionizable functional groups forming anions or anionic groups include, for example, acidic groups or salts of acidic groups.
- the organic groups therefore, include groups derived from organic acids.
- an organic group when an organic group contains an ionizable group forming an anion, such an organic group has a) an aromatic group or a C1-C100 alkyl group and b) at least one acidic group having a pKa of less than 11, or at least one salt of an acidic group having a pK a of less than 1 1 , or a mixture of at least one acidic group having a pK a of less than 1 1 and at least one salt of an acidic group having a pK a of less than 11.
- the pK a of the acidic group refers to the pK a of the organic group as a whole, not just the acidic substituent.
- the pK a is less than 10 and most preferably less than 9.
- the aromatic group or the alkyl group of the organic group is directly attached to the colored pigment.
- the aromatic group may be further substituted or unsubstituted, for example, with alkyl groups.
- the organic group is a phenyl or a naphthyl group and the acidic group is a sulfonic acid group, a sulfinic acid group, a phosphonic acid group, or a carboxylic acid group.
- the organic group is a substituted or unsubstituted sulfophenyl group or a salt thereof; a substituted or unsubstituted carboxyphenyl; a substituted or unsubstituted (polysulfo)phenyl group or a salt thereof; a substituted or unsubstituted sulfonaphthyl group or a salt thereof; or a substituted or unsubstituted (polysulfo)naphthyl group or a salt thereof.
- organic groups having an ionizable functional group forming an anion are p-sulfophenyl (p-sulfanilic acid), 4-hydroxy-3- sulfophenyl (2-hydroxy-5-amino-benzenesulfonic acid), and 2-sulfoethyl (2- aminoethanesulfonic acid).
- p-sulfophenyl p-sulfanilic acid
- 4-hydroxy-3- sulfophenyl (2-hydroxy-5-amino-benzenesulfonic acid
- 2-sulfoethyl 2- aminoethanesulfonic acid
- organic groups that are anionic in nature include, but are not limited to, - C 6 H 4 -COO " X + ; -C 6 H 4 -S0 3 " X + ; -C 6 H 4 -(P0 3 ) "2 2X + ; -C 6 H 2 -(COO " X + ) 3 ; -C 6 H 3 -(COO " X + ) 2 ; - (CH 2 ) z -(COO ' X + ) ; -C 6 H 4 -(CH ) z -(COO " X + ), wherein X + is any cation such as Na + , H + , K + , NH , Li , Ca , Mg and the like and z is an integer from 1 to 18.
- X may be formed in-situ as part of the manufacturing process or may be associated with the aromatic or alkyl group through a typical salt swap or i
- Amines represent examples of ionizable functional groups that form cations or cationic groups and may be attached to the same groups as discussed above for the ionizable groups which form anions.
- amines may be protonated to form ammonium groups in acidic media.
- an organic group having an amine substituent has a pKb of less than 5.
- Quaternary ammonium groups (-NR ), quaternary phosphonium groups (- PR 3 ) and sulfonium groups (-SR 2 ) also represent examples of cationic groups.
- the organic group contains an aromatic group such as a phenyl or a naphthyl group and a quaternary ammonium or a quaternary phosphonium or sulfonium group.
- Quaternized cyclic amines, and even quaternized aromatic amines, can also be used as the organic group.
- N-substituted pyridinium compounds, such as N-methyl-pyridyl can be used in this regard.
- organic groups that are cationic in nature include, but are not limited to, JC 5 H 4 N)C 2 H 5 + Y " , - (C 3 H 5 N 2 ) + Y " (imidizoles), -(C 7 H 7 N 2 ) + N (indizoles), -C6H4COCH 2 (NC 5 H 5 ) + Y " , - (C5H 4 N)CH 3 + N, and -C6H 4 CH 2 N(CH 3 ) 3 Y " , wherein Y " is any halide or an anion such as N0 3 " , OH “ , CH 3 COO " and the like; or combinations thereof.
- Y " may be formed in-situ as part of the manufacturing process or may be associated with the aromatic or alkyl group through a typical salt swap or ion-exchange process.
- Further examples of the ionic or ionizable functional groups include amphiphilic counterions which may be cationic or anionic in nature.
- amphiphilic counterion is a molecule or compound typically described as have a hydrophilic polar "head” and a hydrophobic "tail.”
- Representative examples of cationic and anionic amphiphilic counterions include those set forth and described in U.S. Patent No. 5,698,016 to Adams et al., the entire description of which is incorporated herein by reference.
- an amphiphilic counterion can be used.
- the surface-modified colored pigment as described herein, preferably has a cationic functionality (i.e. positive charge) or anionic functionality (negative charge).
- the charge preferably is created by the ionic or inoizable group of the aromatic group or C1-C100 alkyl group attached to the pigment. If the desired surface-modified colored pigment is anionic in nature, then the amphiphilic counterion will be cationic or positive charging. Similarly, if the surface-modified colored pigment is cationic in nature, then the amphiphilic counterion will be anionic or negative charging.
- Examples of cationic amphiphilic counterions include, but are not limited to, those described ammonium ions that may be formed from adding acids to the following: a fatty amine, an ester of an aminoalcohol, an alkylamine, a polymer containing an amine functionality, a polyethoxylated amine, a polypropoxylated amine, a polyethoxylated polypropoxylated amine, an aniline and derivatives thereof, a fatty alcohol ester of amino acid, a polyamine N-alkylated with a dialkyl succinate ester, a heterocyclic amine, a guanidine derived from a fatty amine, a guanidine derived from an alkylamine, a guanidine derived from an arylamine, an amidine derived from a fatty amine, an amidine derived from a fatty acid, an amidine derived from an alkylamine, or an amidine derived from an arylamine.
- cationic amphiphilic ions include dioctylammonium, oleylammonium, stearylammonium, dodecylammonium, dimethyldodecylammonium, stearylguanidinium, oleylguanidinium, soyalkylammonium, cocoalkylammonium, oleyla moniumethoxylate, protonated diethanolaminedimyristate, and N- oleyldimethylammonium.
- ammonium ions described above the various compounds described above such as fatty amines, esters of amino alcohols, etc., are reacted with an acid such as carboxylic acid, a mineral acid, an alkyl sulfonic acid, or an aryl sulfonic acid.
- an acid such as carboxylic acid, a mineral acid, an alkyl sulfonic acid, or an aryl sulfonic acid.
- Quaternary ammonium salts can also be used as the sources of the cationic amphiphilic ion.
- examples include, but are not limited to, a fatty alkyl trimethyl ammonium, a di(fatty alkyl)dimethylammonium, an alkyl trimethyl ammonium, or 1 -alkyl pyridinium salt, where the counterion is a halide, methosulfate, sulfonate, a sulfate or the like.
- phosphonium salts such as tetraphenylphosphonium chloride can be used as the sources of the amphiphilic ion.
- Cationic amphiphilic ions for use in the present invention include those represented by the formula R 4 N , wherein R is independently hydrogen, G-C 3 o alkyl, G-C 3 o alkenyl, C 7 -C 3 o aralkyl, and C 7 -C 3 o lkaryl.
- R is independently hydrogen, G-C 3 o alkyl, G-C 3 o alkenyl, C 7 -C 3 o aralkyl, and C 7 -C 3 o lkaryl.
- Another example of a suitable amphiphilic ion is a polymer containing an ammonium ion derived from an amine containing polymer.
- the amine containing polymer can be a copolymer of an amine containing monomer, such as dimethylaminoethyl methacrylate or -acrylate, or vinylpyridine or vinylimidazole, and another monomer such as methyl acrylate, methyl methacrylate, butyl acrylate, styrene, and the like.
- the polymer may also be a polyethyleneimine (PEI) derivitized or acylated PEI, polyallylamine, or polydiallylamine.
- PEI polyethyleneimine
- the polymer may also be a ter- or tetra-polymer containing a mixture of an amine containing monomer and two or three other amine containing monomers, respectively.
- Such a polymer may be prepared by any means, such as radical (emulsion, suspension, or solution) or anionic polymerization, stable free radical polymerization or atom transfer polymerization.
- amphiphilic counterion can alternatively ' be an anionic amphiphilic counterion.
- anionic amphiphilic ions include, but are not limited to, an alkylbenzene sulfonate, an alkyl sulfonate, an alkylsulfate, a sulfosuccinate, a sarcosine, an alcohol ethoxylate sulfate, an alcohol ethoxylate sulfonate, an alkyl phosphate, an alkylethoxylated phosphate, an ethoxylated alkylphenol sulfate, a fatty carboxylate, a taurate, an isethionate, an aliphatic carboxylate, or an ion derived from a polymer containing an acid group.
- Sources of specific and preferred examples of anionic amphiphilic ions include, but are not limited to, sodium dodecylbenzene sulfonate, a sodium dodecylsulfate, Aerosol OT, an oleic acid salt, a ricinoleic acid salt, a myrisitic acid salt, a caproic acid salt, sodium 2-octyldodecanoate, sodium bis(2-ethylhexyl)sulfosuccinate, a sulfonated polystyrene, or homo- or copolymers of acrylic acid or methacrylic acid or salts thereof.
- the above-identified amphiphilic counterions and related compounds are commercially available in salt form or can be routinely made by one of ordinary skill in the art.
- a further example of modified pigment product is a colored pigment having attached at least one group comprising the formula:
- X-Sp-[NIon] p R wherein X represents an aromatic group or an alkyl group, NIon represents at least one non-ionic group, Sp represents a spacer group, R represents hydrogen, an aromatic group, or an alkyl group, and p is an integer of from 1 to 500.
- the aromatic group with respect to the X substituent and/or the R substituent can be substituted or unsubstituted and can be, for instance, an aryl or heteroaryl group.
- the aromatic group can be substituted with any group, such as one or more alkyl groups or aryl groups.
- the aromatic group is a phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, pyridinyl, benzothiadiazolyl, or benzothiazolyl.
- Examples of the alkyl group with respect to the X substituent and/or the R substituent include, but are not limited to, substituted or unsubstituted alkyl groups which may be branched or unbranched.
- the alkyl group can be substituted with one or more groups, such as aromatic groups.
- Preferred examples of the alkyl group for purposes of the X substituent include, but are not limited to, Ci-Ci2, like methyl, ethyl, propyl, butyl, pentyl, or. hexyl groups.
- X and/or R can represent a branched or unbranched, substituted or unsubstituted, saturated or unsaturated hydrocarbon.
- substituted groups include, but are not limited to, an ester group, an amide group, an ether group, a carboxyl group, an aryl group, an alkyl group, and the like.
- Sp or the spacer group as used herein is a link between two groups and can be a bond, or a chemical group such as, but not limited to, C0 2 , S0 2 CH 2 CH 2 , CH 2 CH 2 ,
- R represents an organic group such as a substituted or unsubstituted aryl and/or alkyl group.
- non-ionic group examples include, but are not limited to, groups having no apparent ionic charge, such as polymers of ethylene oxide, propylene oxide, other alkylene oxides, carboxylic acid esters, glycols, alcohols, esters, alkanolamine-fatty acid condensates, silicones, isocyanates, alkylpyrrolidenes, and alkylpolyglycosides.
- the non-ionic group in addition to the aforementioned groups, may have carboxylates, sulfonates, phosphates, amines, and other groups that typically demonstrate an ionic nature in water.
- the non-ionic group is preferably a C1-C12 alkyl group, or a G- Ci2 alkylene oxide group, p can be 1-25, 26-50, 51-75, 75-100, and/or 101-500, and p preferably is 5 to 50.
- the X substituent and/or non-ionic group may be substituted with one or more functional groups.
- the functional group preferably contains a lypophilic group.
- Amines also represent examples of functional groups as well as quaternary ammonium groups (-NR 3 ) and quaternary phosphonium groups (-PR 3 ), as well as quaternary sulfonium groups (-SR 2 ).
- the colored pigment product can be a pigment having attached at least one group comprising the formula:
- X represents an aromatic group or an alkyl group
- Sp represents a spacer group
- A represents an alkylene oxide group of from about 1 to about 12 carbons
- p represents an integer of from 1 to 500
- R represents hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group.
- A can be the same of different when p is greater than 1.
- X can be substituted or unsubstituted and can include substituted groups such as an ester group, an amide group, an ether group, a carbonyl group, an aryl group, an alkyl group and the like. The substituted groups can be attached or linked to A.
- alkylene groups include, but are not limited to, -CH2-CH2- 0-; -CH(CH 3 )-CH 2 -O-; -CH 2 CH 2 CH 2 -0-; -CH 2 CHCH 3 -0-; or combinations thereof.
- the colored pigment can be a pigment having attached at least one group comprising the formula: -X-Sp-[(-CH 2 ) m -O-) p -R] wherein X is described above, and for instance can represent an aromatic group or an alkyl group as described earlier, m is an integer of from 1 to 12, preferably 2 or 3, p is an integer of from 1 to 500, Sp represents a spacer group, and R is described above, and for instance can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group.
- R substituents include, but are not limited to, hydrogen, methyl, ethyl, butyl, or propyl groups
- p can be 1-25, 26-50, 51-75, 76-100, and 101 -500, and is preferably 5 to 50.
- Particularly preferred groups of this formula are where X is a phenylene group, m is 1 to 5, and more preferably 2 or 3, p is 5 to 50, more preferably 44-45, and R is hydrogen or a methyl group.
- Another preferred group is where m is 2, p is 7, R is a methyl group, and X is a phenylene group.
- the colored pigment can be a pigment having attached at least one polymeric group, wherein the polymeric group comprises the formula:
- polymer comprises repeating monomer groups or multiple monomer groups or both, optionally having at least one -X' group.
- the 'polymer' can be substituted or unsubstituted with additional groups, and R is described above, and for instance can represent hydrogen, a bond, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic group.
- X represents an alkyl group
- the "polymer” preferably has no ionic or ionizable group.
- X' represents an aromatic group or alkyl group, and each X' and X can be the same or different.
- the total monomer repeating units that comprise the "polymer" is not greater than about 5,000 monomer repeating units.
- X and/or X' can be substituted or unsubstituted and can include substituted groups such as an ester group, an amide group, an ether group, and the like. The substituted groups can be linked to the "polymer.” Also, when R represents a bond, the available bond can be attached to the pigment.
- the polymeric group preferably has no ionic or ionizable group.
- the polymeric group can be any polymeric group capable of being attached to a pigment.
- polymeric groups that comprise the "polymer” can be present.
- the polymeric group can be a thermoplastic polymeric group or a thermosetting polymeric group. Further, the polymeric group can be a homopolymer, copolymer, terpolymer, and/or a polymer containing any number of different repeating units. Further, the polymeric group present in the present invention can be any type of polymeric group, such as a random polymer, alternating polymer, graft polymer, block polymer, star-like polymer, and/or comb-like polymer.
- the polymeric group used in the present invention can also be one or more polyblends.
- the polymeric group can be an interpenetrating polymer network (IPN); simultaneous interpenetrating polymer network (SIN); or interpenetrating elastomeric network (IEN).
- IPN interpenetrating polymer network
- SIEN simultaneous interpenetrating polymer network
- IEN interpenetrating elastomeric network
- polymeric groups include, but are not limited to, linear-high polymers such as polyethylene, poly(vinylchloride), polyisobutylene, polystyrene, polycaprolactam (nylon), polyisoprene, and the like.
- polymeric groups of the present invention are polyamides, polycarbonates, polyelectrolytes, polyesters, polyethers, (polyhydroxy)benzenes, polyimides, polymers containing sulfur (such as polysulfides, (polyphenylene) sulfide, and polysulfones), polyolefins, polymethylbenzenes, polystyrene and styrene copolymers (ABS included), acetal polymers, acrylic polymers, acrylonitrile polymers and copolymers, polyolefins containing halogen (such as polyvinyl chloride and polyvinylidene chloride), fluoropolymers, ionomeric polymers, polymers containing ketone group(s), liquid crystal polymers, polyamide-imides, polymers containing olefinic double bond(s) (such as polybutadiene, polydicyclopentadiene), polyolefin copolymers, polypheny
- polymeric groups of the present invention can be prepared in a number of ways and such ways are known to those skilled in the art.
- the above referenced KIRK- OTHMER section, Modern Plastics Encyclopedia, and C.A. Daniels' reference provide methods in which these polymeric groups can be prepared.
- the polymeric group is preferably a polyolefin group, a polyurethane group, a polystyrenic group, a polyacrylate group, a polyamide group, a polyester group, or mixtures thereof.
- R groups can be the same as previously described above, p can be 1-25, 26-50, 51-75, 76-100, 101-500, and is preferably 1 to 100, and more preferably 5 to 50.
- the organic group(s) attached to the colored pigment can be one or more types of dyes, such as, but not limited to, Nile Blue A, Toluidine Blue, Tryan Blue, C.I. Acid Blue 40, C.I. Acid Blue 129, C.I. Acid Blue 9, C.I. Acid Blue 185, C.I. Direct Blue 71, C.I. Direct Blue 199, C.I. Direct Red 9, C.I. Acid Red 18, C.I. Acid Red 27, C.I. Direct Yellow 86, C.I. Direct Yellow 4, C.I. Acid Yellow 23, and C.I. Food Black 2.
- an organic group having an ionic group and a counterionic group can have a dye serving as the counterionic group.
- Attaching a dye to the colored pigment can provide the advantage of modifying the color properties of pigments.
- the organic group(s) attached to the colored pigment can be one or more types of light stabilizers, e.g., hindered amine light stabilizer (HALS) or antioxidant.
- HALS hindered amine light stabilizer
- the modified particle can be a polymer coated modified pigment product.
- the modified pigment product is at least partially coated with one or more polymers and can be substantially or fully coated by one or more polymers.
- the use of the term "coated” includes partially and fully coated carbon products and modified pigment products.
- the polymer in this invention partially or fully encapsulates the modified pigment product, wherein the modified pigment product is the core and the polymer is the shell.
- the polymer(s) coated onto or used to encapsulate the modified pigment product is preferably present on the modified pigment product such that the polymer(s) is not substantially extractable by a solvent.
- the polymer(s) on the modified pigment product is attached by physical (e.g., adsorption) and/or chemical means (e.g. chemical bonding, grafting).
- the pigment product coated with a polymer can be a modified pigment product having at least one organic group attached to the pigment product.
- the organic group is substituted with an ionic, ionizable, or polar group.
- the pigment product which has the organic group attached thereto can be any pigment product capable of having at least one organic group attached to the pigment product.
- organic groups having an a inophenyl such as (CJJ 4 )-NH 2 , (C 6 H 4 )-CH 2 -(C 6 H 4 )-NH 2 , (CJJ 4 )-SO 2 - (C 6 H 4 )-NH 2 .
- Organic groups also include aromatic sulfides, represented, for instance, by the formulas Ar-S n -Ar' or Ar-S n -Ar", wherein Ar and Ar' are independently arylene groups, Ar" is an aryl and n is 1 to 8.
- the organic group comprises an aromatic group and/or a G-Goo alkyl group (and more preferably a C,-C ]2 alkyl group) directly attached to the pigment, preferably with an ionic, ionizable, or polar group.
- More than one type of organic group can be attached to the pigment, or two or more modified pigments with different attached organic groups can be used. Using two or more different types of organic groups permits a combination of properties. If two different types of organic groups are attached, for example, a sulfanilic group and a styrenic group, the sulfanilic group promotes dispersibility and the styrenic group serves as a radical grafting site.
- the ratio of the different organic groups can be the same or different.
- only the minimum treatment level of the ionic, ionizable, or polar group is used to impart stability to the dispersion.
- groups such as ionic species (e.g., sulphates, phosphates, alkali salts of organic acids or quaternary ammonium salts), non-ionic species (e.g., hydroxyl, organic acids) or surfactant stabilizers (e.g., SDMS, SDS, Antarox) can be used to provide stable pigment dispersions in aqueous media. Dispersion of the modified pigment in organic liquids can be facilitated in a similar manner but employing treatments which are more compatible with these less polar environments. Treatment levels of the organic group for purposes of radical grafting sites would depend on material uses.
- attachment of epoxy groups would facilitate grafting to hydroxyl bearing polymer matrices such as polyurethanes or polycarbonates or amine matrices such as nylon.
- Other examples include the attachment of radical sensitive vinyl groups such as styrenics or acrylates, or methacrylates, to facilitate crosslinking type reactions in radical polymerizations.
- a combination of different modified pigment can be used.
- a modified pigment having one type of organic group attached thereto can be used in combination with another modified pigment having a different organic group attached thereto.
- a modified pigment such as an aggregate comprising a carbon phase and a silicon-containing species phase can be used in combination with a modified carbon product having an attached organic group, and so on.
- the modified pigment which is coated with one or more polymers can have any particle size and/or surface area so long as the particle is capable of being at least partially coated with one or more polymers.
- the primary particle size of the modified pigment is from about 5 nm to about 100 nm and more preferably from about 8 nm to about 75 nm.
- the nitrogen surface area as measured by the BET method, of the modified carbon product is preferably from about 20 m /g to about 1500 m /g and more preferably from about 25 m /g to about 700 m 2 /g and most preferably from about 30 m 2 /g to about 250 m 2 /g.
- the thickness of the coating on the modified pigment can be uniformed or can vary in thickness.
- the thickness of the coating can be about 1 nm or more.
- the polymer coated onto the modified carbon product is substantially uniform in thickness.
- the thickness of the polymer coating on the modified pigment is from about 10 nm to about 100 nm, more preferably from about 20 nm to about 75 nm, and most preferably from about 30 nm to about 50 nm.
- the modified carbon product can have more than one coating or shell.
- the modified pigment can have multiple layers of shells or coatings which partially or fully encapsulate the modified carbon product or a previous coating or shell.
- the polymers comprising the various layers can be the same or different. For instance, one layer can be cross-linked while the next layer can be not cross-linked.
- Each of the various coatings, if more than one is present on the modified carbon product, can be substantially the same or vary in thickness if desired.
- the polymer which is coated onto the modified carbon product can be a homo- polymer, copolymer, terpolymer, and/or a polymer containing any number of different repeating units.
- the polymer can be any type of polymer, such as a random polymer, alternating polymer, graft polymer, block polymer, star-like polymer, and/or comb-like polymer.
- the polymer can also be one or more polyblends.
- the polymer can be an interpenetrating polymer network (JPN); simultaneous interpenetrating polymer network (SIN); or interpenetrating elastomeric network (IEN).
- JPN interpenetrating polymer network
- SIIN simultaneous interpenetrating polymer network
- IEN interpenetrating elastomeric network
- the polymer can be thermoplastic or thermosettable.
- polymers include, but are not limited to, linear and non-linear polymers such as polyethylene, poly(vinylchloride), polyisobutylene, polystyrene, polycaprolactam (nylon), polyisoprene, and the like.
- polymers include polyamides, polycarbonates, polyelectrolytes, polyesters, polyethers, (polyhydroxy)benzenes, polyimides, polymers containing sulfur (such as polysulfides, (polyphenylene) sulfide, and polysulfones, polyolefins, polymethylbenzenes, polystyrene and styrene copolymers (ABS included), acetal polymers, acrylic polymers, acrylonitrile polymers and copolymers, polyolefins containing halogen (such as polyvinyl chloride and polyvinylidene chloride), fluoropolymers, ionomeric polymers, polymers containing ketone group(s), liquid crystal polymers, polyamide-imides, polymers containing olefinic double bond(s) (such as polybutadiene, polydicyclopentadiene), polyolefin copolymers, polyphenylene oxides, poly
- the polymer is an acrylic polymer, a methacrylic polymer, or a styrenic polymer, but would largely depend upon the intended application.
- reinforcement applications would generally involve the formation of a rubber product that could be attached to the modified carbon product in a manner such that the rubber product is preferably not extractable, e.g., not extractable in solvents. This can be accomplished by using a modified carbon product that has styrenic groups attached to the surface. During an aqueous media radical polymerization, the propagating chains could graft to these sites on the surface of the modified carbon product and generate a rubbery coated particle.
- the polymer coated modified pigments can be made by a number of ways.
- the modified pigments are made by, but are not limited to, aqueous mediated polymerization environments such as emulsion polymerization or suspension polymerization processes as well as solvent based polymerizations.
- the polymerizations involved are generally chain growth polymerizations and/or step growth polymerizations.
- the modified pigment has at least one organic group attached to the pigment particles and the organic group is positively chargeable.
- the organic group can be attached to the pigment in various amounts, i.e., low to high amounts, thus allowing fine control over charge modification.
- the organic group that is attached to the pigment particles can be any group which permits the modified pigment to be positively chargeable once incorporated into the dielectric fluid.
- the organic group comprises an aromatic group or a C1-C20 alkyl group, wherein either group can be substituted or unsubstituted. It is also preferred that the aromatic group or G-C20 alkyl group is directly attached to the pigment particles.
- Preferred groups of positively chargeable organic groups are nitrogen containing or phosphorus containing organic groups.
- Preferred positive chargeable organic groups have the general structures:
- Q represents the elements nitrogen or phosphorus
- X represents a counterion such as Cl “ , Br “ , ArS0 3 " , and the like
- Ri represents an alkylene group or an arylene group attached to the pigment
- R 2 , R 3 , and R 4 which may be the same or different, each represent an alkyl group or an aryl group.
- the alkylene or alkyl group is a G-Go alkylene or alkyl group and the arylene or aryl group is a C ⁇ -C 2 o arylene or aryl group.
- aryl and arylene groups include heteroaryl and heteroarylene groups, respectively.
- Ar represents an aromatic group and Ar' represents an aromatic group.
- the aromatic group includes, but is not limited to, unsaturated cyclic hydrocarbons containing one or more rings.
- the aromatic group may be substituted or unsubstituted.
- Aromatic groups include aryl groups (for example, phenyl, naphthyl, anthracenyl, and the like), and heteroaryl groups(imidazolyl, pyrazolyl, pyridinyl, thienyl, thiazolyl, furyl, triazinyl, indolyl, and the like).
- negatively chargeable particles can be produced using the appropriate functional groups, such as sulfamides.
- a combination of organic groups such as an organic group comprising a pyridyl group and an organic group comprising a quaternary ammonium group can be used.
- the organic group is a Ci-Cioo alkyl group (more preferably a C1-C12 alkyl group), an aromatic group, or other organic group, monomeric group, or polymeric group, each optionally having a functional group or ionic or ionizable group. More preferably, these groups are directly attached to the particles.
- the polymeric group can be any polymeric group capable of being attached to a particle.
- the polymeric group can be a polyolefin group, a polystyrenic group, a polyacrylate group, a polyamide group, a polyester group, or mixtures thereof.
- Monomeric groups are monomeric versions of the polymeric groups.
- the organic group can also be an olefin group, a styrenic group, an acrylate group, an amide group, an ester, or mixtures thereof.
- the organic group can also be an aromatic group or an alkyl group, either group with an olefin group, a styrenic group, an acrylate group, an amide group, an ester group, or mixtures thereof, wherein preferably the aromatic group, or the alkyl group, like a O-C12 group, is directly attached to the particle.
- the polymeric group can include an aromatic group or an alkyl group, like a G-C 12 group, either group with a polyolefin group, a polystyrenic group, a polyacrylate group, a polyamide group, an polyester group, or mixtures thereof.
- the organic group can also comprise an aralkyl group or alkylaryl group, which is preferably directly attached to the carbon product.
- Other examples of organic groups include a C1-G00 alkyl group, and more preferably a C 2 o-C 6 o alkyl group.
- organic groups having the following formulas (hyphens on one or more ends represents an attachment to a particle or to another group):
- the various organic, monomeric, and polymeric groups described above and below which are part of the modified particles can be unsubstituted or substituted and can be branched or linear.
- one or more organic groups can be attached to the pigment. Further, two or more modified pigments, each having a different organic group attached to the pigment, can be used. Also, one organic group having an ionic or ionizable group can be used in connection with a second or additional organic groups with or without ionic or ionizable groups and so on.
- the microscopic containers can contain particles having particles wherein a portion of the particles have one type of organic group attached onto the particles and another portion of the particles have a different organic group attached to the particles.
- the advantage of such a system would make it possible to have organic groups having ionic and/or ionizable groups such that their response to a potential difference is different.
- one organic group may have ionic and/or ionizable groups having a greater affinity for a positive or negative charge compared to other particles having a different organic group with an ionic and/or ionizable group. This type of situation may permit the ability to achieve multi-color displays with numerous options.
- the microscopic containers can be different.
- a portion of the microscopic containers can contain one type of particles having an organic group with an ionic and/or ionizable group and another portion of microscopic containers can contain particles with a different type of organic group having an ionic and/ionizable group wherein the response to a potential difference between the different types of microscopic containers can be different again creating the ability to have a multi-color display.
- the particles having the different types of organic groups as described above would preferably involve particles having different colors so that one particle would have one color while a second particle would have a different color as well as a different organic group having an ionic and/or ionizable group having a different response to a potential difference between the electrodes thus creating different electrophoretic mobilities which are preferably substantially non-overlapping in order to create various multi-colored displays.
- controlling the electric field permits the desired display described in U.S. Patent No. 6,017,584 incorporated in its entirety by reference herein.
- the present invention can alter and/or create the desired zeta potential on the various particles in order to achieve the desired electrophoretic mobility of the various particles.
- conventional particles e.g., charged or uncharged
- the improvements described in various electrophoretic display systems can also be incorporated into the present invention such as using reflective components, placing a charge opposite in polarity to the particles on the inside walls of the microscopic containers, using liquid crystal materials whose orientation is affected by the electric field, and the like.
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Abstract
L'invention concerne un affichage électrophorétique contenant des particules modifiées, ainsi que des systèmes d'affichage non émissifs. Dans l'affichage électrophorétique, on utilise un arrangement de contenants microscopiques dans lequel chaque contenant contient un fluide diélectrique et une suspension de particules auxquelles est attaché au moins un groupe organique, ce groupe organique comprenant au moins un groupe ionique, un groupe ionisable, ou les deux, et dans lequel le fluide et les particules contrastent visuellement. L'affichage électrophorétique comprend aussi des première et seconde électrodes, l'arrangement étant placé entre ces électrodes, l'une de ces électrodes étant sensiblement visuellement transparente. L'affichage électrophorétique comprend aussi des moyens de création d'une différence de potentiel entre les deux électrodes de façon que cette différence de potentiel fasse migrer les particules vers l'une des électrodes.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US65803000A | 2000-09-08 | 2000-09-08 | |
US658030 | 2000-09-08 | ||
PCT/US2001/028189 WO2002021201A2 (fr) | 2000-09-08 | 2001-09-07 | Affichages electrophoretiques contenant des particules modifiees |
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EP1356346A2 true EP1356346A2 (fr) | 2003-10-29 |
Family
ID=24639622
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP01968713A Withdrawn EP1356346A2 (fr) | 2000-09-08 | 2001-09-07 | Affichages electrophoretiques contenant des particules modifiees |
Country Status (5)
Country | Link |
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EP (1) | EP1356346A2 (fr) |
JP (1) | JP2004527776A (fr) |
AU (1) | AU2001288943A1 (fr) |
CA (1) | CA2421883A1 (fr) |
WO (1) | WO2002021201A2 (fr) |
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JP4623972B2 (ja) * | 2003-01-14 | 2011-02-02 | ナトコ株式会社 | 電気泳動性着色粒子および表示素子 |
CN100354742C (zh) | 2003-01-17 | 2007-12-12 | 皇家飞利浦电子股份有限公司 | 电泳显示器 |
WO2006126120A1 (fr) * | 2005-05-27 | 2006-11-30 | Koninklijke Philips Electronics N.V. | Systeme multiparticulaire robuste pour affichages electrophoretiques couleurs a tensions de commande tres basses comprenant une faible quantite d'electrolytes |
US7344750B2 (en) | 2006-05-19 | 2008-03-18 | Xerox Corporation | Electrophoretic display device |
US7652656B2 (en) | 2006-05-19 | 2010-01-26 | Xerox Corporation | Electrophoretic display and method of displaying images |
US7433113B2 (en) | 2006-05-19 | 2008-10-07 | Xerox Corporation | Electrophoretic display medium and device |
US7345810B2 (en) | 2006-05-19 | 2008-03-18 | Xerox Corporation | Electrophoretic display and method of displaying images |
US7403325B2 (en) | 2006-05-19 | 2008-07-22 | Xerox Corporation | Electrophoretic display device |
US7443570B2 (en) | 2006-05-19 | 2008-10-28 | Xerox Corporation | Electrophoretic display medium and device |
US7430073B2 (en) * | 2006-05-19 | 2008-09-30 | Xerox Corporation | Electrophoretic display device and method of displaying image |
US7502161B2 (en) | 2006-05-19 | 2009-03-10 | Xerox Corporation | Electrophoretic display medium and device |
US7440159B2 (en) | 2006-05-19 | 2008-10-21 | Xerox Corporation | Electrophoretic display and method of displaying images |
US7492504B2 (en) | 2006-05-19 | 2009-02-17 | Xerox Corporation | Electrophoretic display medium and device |
US7417787B2 (en) | 2006-05-19 | 2008-08-26 | Xerox Corporation | Electrophoretic display device |
CA2656717A1 (fr) * | 2006-07-06 | 2008-01-10 | Ciba Holding Inc. | Dispersions encapsulees comprenant des colorants organiques mobiles par electrophorese |
EP2198340B1 (fr) * | 2007-09-07 | 2019-03-13 | Basf Se | Dispersions encapsulées comprenant des colorants organiques mobiles électrophorétiques |
JP5499438B2 (ja) * | 2008-02-13 | 2014-05-21 | 富士ゼロックス株式会社 | 表示用粒子及びその製造方法、表示用粒子分散液、表示媒体、並びに、表示装置 |
JP5401799B2 (ja) * | 2008-02-13 | 2014-01-29 | 富士ゼロックス株式会社 | 画像表示用粒子、画像表示用粒子分散液、表示媒体、及び表示装置 |
JP5012839B2 (ja) * | 2009-03-17 | 2012-08-29 | 富士ゼロックス株式会社 | 表示用粒子分散液、表示媒体、及び表示装置 |
WO2011046564A1 (fr) * | 2009-10-16 | 2011-04-21 | Hewlett-Packard Development Company, L.P. | Encre adressable électroniquement à deux couleurs |
US9835926B2 (en) | 2012-03-21 | 2017-12-05 | E Ink California, Llc | Electrophoretic dispersion |
US10288975B2 (en) | 2012-03-21 | 2019-05-14 | E Ink California, Llc | Electrophoretic dispersion including charged pigment particles, uncharged additive nanoparticles, and uncharged neutral density particles |
US9052564B2 (en) | 2012-03-21 | 2015-06-09 | E Ink California, Llc | Electrophoretic dispersion |
US8927648B2 (en) | 2012-05-04 | 2015-01-06 | Cabot Corporation | Surface modification of pigments and compositions comprising the same |
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US5914806A (en) * | 1998-02-11 | 1999-06-22 | International Business Machines Corporation | Stable electrophoretic particles for displays |
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US4285801A (en) * | 1979-09-20 | 1981-08-25 | Xerox Corporation | Electrophoretic display composition |
JPS60189731A (ja) * | 1984-03-09 | 1985-09-27 | Nippon Paint Co Ltd | 電気泳動表示装置用分散液組成物 |
JPS62183439A (ja) * | 1986-02-07 | 1987-08-11 | Ricoh Co Ltd | 電気泳動表示素子 |
JPS62232623A (ja) * | 1986-04-02 | 1987-10-13 | Ricoh Co Ltd | 電気泳動表示素子 |
JPS638637A (ja) * | 1986-06-27 | 1988-01-14 | Ricoh Co Ltd | 電気泳動表示素子 |
JPH03249739A (ja) * | 1990-02-28 | 1991-11-07 | Hitachi Chem Co Ltd | 電気泳動表示装置用表示液及びその表示液を用いた電気泳動表示装置 |
JPH04166918A (ja) * | 1990-10-31 | 1992-06-12 | Hitachi Chem Co Ltd | 電気泳動表示装置用表示液及びその表示液を用いた電気泳動表示装置 |
US6017584A (en) * | 1995-07-20 | 2000-01-25 | E Ink Corporation | Multi-color electrophoretic displays and materials for making the same |
US5837045A (en) * | 1996-06-17 | 1998-11-17 | Cabot Corporation | Colored pigment and aqueous compositions containing same |
US5930026A (en) * | 1996-10-25 | 1999-07-27 | Massachusetts Institute Of Technology | Nonemissive displays and piezoelectric power supplies therefor |
US5961804A (en) * | 1997-03-18 | 1999-10-05 | Massachusetts Institute Of Technology | Microencapsulated electrophoretic display |
ATE280963T1 (de) * | 1997-08-28 | 2004-11-15 | E Ink Corp | Neue adressierungsschaltungen für elektrophoretische anzeigevorrichtungen |
JPH11119704A (ja) * | 1997-10-13 | 1999-04-30 | Brother Ind Ltd | 表示装置 |
JPH11143407A (ja) * | 1997-11-11 | 1999-05-28 | Brother Ind Ltd | 表示装置 |
AU3767899A (en) * | 1998-04-27 | 1999-11-16 | E-Ink Corporation | Shutter mode microencapsulated electrophoretic display |
AU6293699A (en) * | 1998-10-07 | 2000-04-26 | E-Ink Corporation | Encapsulated electrophoretic displays having a monolayer of capsules |
JP2000122103A (ja) * | 1998-10-19 | 2000-04-28 | Sony Corp | 表示装置 |
JP2000194020A (ja) * | 1998-12-28 | 2000-07-14 | Sony Corp | 表示装置 |
-
2001
- 2001-09-07 JP JP2002524758A patent/JP2004527776A/ja active Pending
- 2001-09-07 EP EP01968713A patent/EP1356346A2/fr not_active Withdrawn
- 2001-09-07 CA CA002421883A patent/CA2421883A1/fr not_active Abandoned
- 2001-09-07 AU AU2001288943A patent/AU2001288943A1/en not_active Abandoned
- 2001-09-07 WO PCT/US2001/028189 patent/WO2002021201A2/fr not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US5914806A (en) * | 1998-02-11 | 1999-06-22 | International Business Machines Corporation | Stable electrophoretic particles for displays |
Also Published As
Publication number | Publication date |
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WO2002021201A2 (fr) | 2002-03-14 |
CA2421883A1 (fr) | 2002-03-14 |
AU2001288943A1 (en) | 2002-03-22 |
WO2002021201A3 (fr) | 2003-08-07 |
JP2004527776A (ja) | 2004-09-09 |
WO2002021201A9 (fr) | 2003-11-13 |
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