WO2006126566A1 - 液体現像剤およびその製造方法 - Google Patents
液体現像剤およびその製造方法 Download PDFInfo
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- WO2006126566A1 WO2006126566A1 PCT/JP2006/310311 JP2006310311W WO2006126566A1 WO 2006126566 A1 WO2006126566 A1 WO 2006126566A1 JP 2006310311 W JP2006310311 W JP 2006310311W WO 2006126566 A1 WO2006126566 A1 WO 2006126566A1
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/122—Developers with toner particles in liquid developer mixtures characterised by the colouring agents
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
- G03G9/131—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
- G03G9/132—Developers with toner particles in liquid developer mixtures characterised by polymer components obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/12—Developers with toner particles in liquid developer mixtures
- G03G9/13—Developers with toner particles in liquid developer mixtures characterised by polymer components
- G03G9/133—Graft-or block polymers
Definitions
- the present invention relates to a liquid developer for electrophotography or electrostatic recording used for a printing machine, a copying machine, a printer, a facsimile, and the like, and a method for producing the same.
- a colorant and a resin are heated at a temperature equal to or higher than the melting point of the resin-kneaders such as a single roll and a three roll mill. After kneading and cooling, the resulting mixture is dry pulverized, and the pulverized product is wet pulverized using a dispersant and an electrically insulating water-insoluble agent to create a toner concentrate, and charge control is further performed.
- the object of the present invention is to provide a liquid developer capable of high solid content and having excellent developability. And a method of manufacturing the same.
- the present invention provides the following liquid developer and method for producing the same.
- modified novolak candy wherein a colored chip obtained by heating and kneading a pigment and a thermoplastic resin has a ring-opening structure of an epoxy group with an aromatic ring and a carboxyl group derived from hydroxycarboxylic acid It is characterized in that it is dispersed by wet pulverization in an electrically insulating hydrocarbon solvent in which at least one pigment dispersant selected also from the group consisting of the fat (A) and the copolymer (B) is dissolved. Liquid developer.
- a modified novolac rosin At least 1 group represented by the general formula (1) by ring opening of an epoxy group by a carboxyl group derived from hydroxycarboxylic acid and an aromatic ring derived from novolak resin is included in the molecule.
- the oxygen atom at the left end is derived from the oxygen atom contained in the aromatic hydroxyl group of the novolak resin, and W 1 and X 1 are each independently a divalent carbon atom having 1 to 19 carbon atoms.
- Copolymer (B) a copolymer having a weight average molecular weight of 3,000 to 100,000, wherein the constituent unit represented by the general formula (2) in the copolymer corresponds to at least 10 mol%.
- W 2 and X 2 are each independently a divalent hydrocarbon group having 1 19 carbon atoms
- R 2 R 3 and R 4 are each independently a hydrogen atom or a methyl group
- R 5 is a hydrogen atom or a halogen atom
- R 6 and R 7 are each independently a hydrogen atom, a hydrocarbon group having 15 carbon atoms
- R 8 represents a hydrogen atom or a methyl group.
- R 9 represents a direct bond or a methylene group
- a colored chip obtained by heating and kneading a pigment and a thermoplastic resin is preliminarily dry-pulverized into a coarsely pulverized product, and the modified novolac resin (A) and copolymer (B
- the coarsely pulverized product is wet-pulverized in an electrically insulating hydrocarbon-based solvent in which at least one pigment dispersant selected from the group consisting of (1) to (4) is dissolved.
- inorganic pigments and organic pigments conventionally used in liquid developers can be used without any particular limitation.
- carbon black such as acetylene black, graphite, bengara, yellow lead, ultramarine And inorganic pigments such as azo pigments, condensed azo pigments, lake pigments, phthalocyanine pigments, isoindoline pigments, anthraquinone pigments, quinatalidone pigments.
- organic pigments of various hues magenta organic pigments, quinacridone pigments such as quinacridone red, azo pigments such as permanentol, condensed azo pigments such as condensed azo red, and perylene red such as perylene red And pigments.
- cyan organic pigments examples include phthalocyanine pigments such as metal-free phthalocyanine blue, phthalocyanine blue, and fast sky nore.
- yellow organic pigments include monoazo pigments such as Hansa Yellow, disazo pigments such as benzine yellow and permanent yellow, and condensed azo pigments such as condensed azo yellow.
- green pigments include phthalocyanine pigments such as phthalocyanine green. These pigments can be used alone or in combination of two or more. Can be used.
- the pigment content in the liquid developer is not particularly limited! From the standpoint of image density, 1 to 20 parts by mass is preferred per 100 parts by mass of the final liquid developer.
- thermoplastic resin used in the present invention a known thermoplastic resin used in a liquid developer can be used, is insoluble in an electrically insulating hydrocarbon solvent, and preferably is electrically insulated.
- the swelling degree with respect to the basic hydrocarbon solvent is low. If the degree of swelling of the thermoplastic rosin is high, it is difficult to achieve high solid differentiation, and if the development speed is increased, problems such as the occurrence of capri and stains in the non-image area of the image are likely to occur.
- thermoplastic resin examples include polyester-based resins, epoxy-based resins, acrylic-based resins, styrene-based resins, styrene-acrylic-based copolymer resins, polysalt-based vinyl resins, and polyacetic acids. Bull resin, polyethylene resin, polypropylene resin, polyurethane resin, polyvinyl pentyl resin, rosin resin, modified rosin resin, terpene resin, phenol resin, aliphatic hydrocarbon resin, aromatic Synthetic resins such as petroleum oils or natural oils. These thermoplastic resin can be used alone or in admixture of two or more.
- the total ratio of the pigment and the thermoplastic resin in the liquid developer of the present invention is preferably 10 to 50% by mass, more preferably 15 to 40% by mass. If the total ratio of the pigment and the thermoplastic resin is less than the above range! /, A sufficient concentration of the liquid developer may not be obtained. If it exceeds the above range, the viscosity of the liquid developer increases. May cause problems.
- the electrically insulating hydrocarbon solvent used in the present invention is a solvent that does not dissolve the thermoplastic resin, and is an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a halogeni.
- a material having a volume resistivity (approximately 10 u to 10 16 ⁇ ⁇ cm) that does not disturb the electrostatic latent image such as hydrocarbon can be used.
- high boiling points normal boiling point 150 ° C at normal pressure
- normal paraffin solvent isoparaffin solvent, cycloparaffin solvent, or a mixture of two or more of them due to odor, harmlessness and cost.
- the above paraffinic solvent is preferred.
- paraffinic solvents such as normal paraffinic solvent, isoparaffinic solvent, cycloparaffinic solvent or mixtures thereof include, for example, ISOPER G, ISOPAR H, ISOPAR L, ISOPAR M, ethanol D130, and ethanol D. 140 (and above, manufactured by Sexon Chemical Co., Ltd.), Shellsol 71 (manufactured by Shell Petrochemical Co., Ltd.), IP Solvent 1620, IP Solvent 2080, IP Solvent 2835 (all above, Idemitsu Petrochemical Co., Ltd.) ), Moresco White P-40, Moresco White P-55, Moresco White P-80 (all of which are manufactured by Matsumura Oil Research Co., Ltd.), Liquid Paraffin No. 40-S, Liquid Paraffin No. 55—S (all of which are manufactured by Chuo Kosei Co., Ltd.) and the like are preferable.
- the pigment dispersant used in the present invention is at least one pigment dispersant selected from the group consisting of the modified novolac resin (A) and the copolymer (B), and is electrically insulating. Those that are soluble in water-soluble hydrocarbon solvents are used.
- the copolymer (B) has a relatively large side chain represented by the general formula (2) hanging from the main chain. Seen in coalescence. From this point, the copolymer (B) is hereinafter referred to as a graft copolymer (B).
- polyvalent phenols such as monovalent phenols or trihydroxybenzene and aldehydes and a novolac resin that is force-induced are used. can do.
- monovalent phenols are unsubstituted such as phenol, cresol, xylenol, trimethylphenol, propylphenol, butinolevenol, amylphenol, hexylphenol, octylphenol, norphenol, dodecylphenol, etc.
- Phenols having an aromatic substituent such as phenols or alkyl-substituted phenols, monohydroxydiphenol methane, or phenol phenol can be used.
- di- or trihydroxybenzenes such as catechol, resorcinol, hydroquinone or trihydroxybenzene, or alkyl or aromatic substituents thereof can be used.
- dihydroxydiphenylmethanes such as bisphenol A and bisphenol F, and dihydroxybutyrate can also be used.
- halogen-substituted products of the above phenols can be used, and examples thereof include chlorinated or brominated phenols. These phenols can be used alone or in admixture of two or more.
- phenols in terms of reactivity, monovalent phenols are phenol and meta positions. Is preferably a phenol substituted with one alkyl group, and a polyhydric phenol is preferably resorcinol.
- aldehydes those generally used in the production of novolak rosin can be used without particular limitation. Specifically, lower aliphatic aldehydes such as formaldehyde, paraformaldehyde, trioxane and cyclic formals, acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, daroxal, and aromatics such as furfural and phenol aldehyde. Examples include aldehydes. These aldehydes can be used alone or in admixture of two or more.
- novolak rosin these compounds can be synthesized by conventional methods in the presence of an acid catalyst such as paratoluenesulfonic acid, perchloric acid, hydrochloric acid, nitric acid, sulfuric acid, black acetic acid, oxalic acid, and phosphoric acid.
- an acid catalyst such as paratoluenesulfonic acid, perchloric acid, hydrochloric acid, nitric acid, sulfuric acid, black acetic acid, oxalic acid, and phosphoric acid.
- a novolac resin may be synthesized by a method using a phenol derivative having a hydroxymethyl group such as saligenin, or a phenol derivative having a halogenated methyl group such as o-methylphenol.
- the novolac resin is reacted with epichlorohydrin or ⁇ -methyl epichlorohydrin by a conventional method to obtain a novolac resin having an epoxy group.
- a novolac resin having a commercially available epoxy group can also be used.
- the novolak resin having epoxy groups is reacted with carboxylic acids and amines described later to obtain the desired modified novolac resin ( ⁇ ).
- This reaction can be carried out by heating to 60 to 160 ° C. using a solvent as necessary and using a catalyst such as aliphatic amine, aromatic amine or ammonium salt as necessary. The progress of the reaction can be followed by measuring the molecular weight by GPC, measuring the epoxy equivalent, and so on.
- the aromatic hydroxyl group of the monohydric phenol or polyhydric phenol described above is added to epichlorohydrin or ⁇ -methyl epoxy. It reacts with chlorohydrin to form a glycidyloxy group or a 2,3 epoxy 2-methylpropyloxy group, which reacts with carboxylic acids and amines described later, and then, if necessary, a new phenol. And use aldehydes to make novolat
- the modified novolak oxalate (A) can also be obtained by carrying out the oxalation reaction.
- the group represented by the general formula (1) in the modified novolak rosin (A) is an aromatic hydroxyl group.
- Epichlorohydrin or j8-methyl epichlorohydrin then having an unsaturated bond or a branched structure, a hydroxycarboxylic acid having 2 to 20 carbon atoms, a mixture thereof, or It can be obtained by reacting the polycondensate.
- the oxygen atom at the left end is derived from an oxygen atom contained in the aromatic hydroxyl group of the novolak resin, and w 1 and X 1 have an unsaturated bond and Z or a branched structure.
- R 1 represents a hydrogen atom or a methyl group, which may be a divalent hydrocarbon group having 1 to 19 carbon atoms.
- X 1 and j are the same as defined above
- X 1 and j are hydroxycarboxylic acids in the range of 2 to 20 carbon atoms which may have an unsaturated bond and Z or a branched structure, these It is also possible to induce a mixture of these or their polycondensate power.
- Examples of the hydroxycarboxylic acid include glycolic acid, lactic acid, oxybutyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxycaprylic acid, hydroxycapric acid, hydroxylauric acid, hydroxymyristic acid, hydroxypalmitic acid, ricinoleic acid and castor oil.
- Examples thereof include fatty acids and hydrogenated products thereof, 12-hydroxystearic acid and the like.
- a hydroxycarboxylic acid such as can be preferably used.
- the number of repetitions i is an integer in the range of 1 to 30, and j is an integer in the range of 0 to 30.
- the appropriate value varies depending on the type of pigment used, the specific surface area and particle diameter of the pigment particles, the properties of the pigment surface treatment agent, the type of thermoplastic resin, the polarity of the dispersion medium, etc. It is necessary to select an optimum value according to each case. However, in general, it is preferable that j ⁇ 2 and i + j ⁇ 2. Even if the value of j exceeds the above range, the dispersibility cannot be further improved.
- the formation of the group represented by the general formula (5) or the general formula (6) in the general formula (1) is, for example, by previously synthesizing a polyester by polycondensation of hydroxycarboxylic acid, and then terminal carboxyl groups. Can be reacted with the above-mentioned epoxy group, or after the carboxyl group of hydroxycarboxylic acid is reacted with the above-mentioned epoxy group, the hydroxycarboxylic acid is further polycondensed.
- the polycondensation reaction of the hydroxycarboxylic acid is carried out in the presence or absence of a catalyst such as p-toluenesulfonic acid, stannous octylate, dibutyltin diacetate, tetra-n-butyl titanate and the like. It can be carried out while heating and stirring at 180 to 220 ° C., and removing the produced water with an azeotropic solvent such as toluene-xylene. The reaction can be followed by measuring the molecular weight by GPC, acid value, etc.
- a catalyst such as p-toluenesulfonic acid, stannous octylate, dibutyltin diacetate, tetra-n-butyl titanate and the like. It can be carried out while heating and stirring at 180 to 220 ° C., and removing the produced water with an azeotropic solvent such as toluene-xylene.
- the reaction can be
- the modified novolak rosin (A) must always have a group represented by the general formula (1) in the molecule! /.
- the number of groups represented by the general formula (1) is preferably 1-20. In this case, sufficient dispersibility cannot be obtained. Although there is an effect even if the number of the groups exceeds the above range, it is very difficult to control the molecular weight of the novolak rosin having a large number of nuclei necessary for that purpose, so 20 is practically the upper limit.
- the appropriate value varies depending on the type of pigment, the specific surface area and particle diameter of pigment particles, the presence or absence of pigment surface treatment agent or its properties, the type of thermoplastic resin, the polarity of the dispersion medium, etc. It is necessary to select the optimum value according to the application.
- modified novolak rosin (A) is further represented by the general formula (7) in the molecule:
- the oxygen atom at the left end is derived from an oxygen atom contained in the aromatic hydroxyl group of the novolak resin, and Y has an oxygen atom or a nitrogen atom at the connection end and has a carbon number power of ⁇ ⁇ 20.
- R 1Q represents a hydrogen atom or a methyl group] except for a monovalent organic group in the range (excluding the group represented by the general formula (5)). ! /
- the group represented by the general formula (7) is obtained by reacting an aromatic hydroxyl group with epichlorohydrin or ⁇ -methyl epichlorohydrin, and then reacting with a monovalent carboxylic acid or monovalent carboxylic acid. It can be obtained by reacting amines. Since basic groups formed by reacting monovalent amines tend to adversely affect charging characteristics, it is preferable not to use monovalent amines. When using monovalent amines, it is necessary to pay attention to the amount used.
- monovalent carboxylic acids include saturated fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, strong prillic acid, strong puric acid, lauric acid, myristic acid, palmitic acid, stearic acid, Unsaturated fatty acids such as oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, eleostearic acid, and hydrogenated products thereof can be used.
- saturated fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, strong prillic acid, strong puric acid, lauric acid, myristic acid, palmitic acid, stearic acid, Unsaturated fatty acids such as oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, eleostearic acid, and hydrogenated products thereof can be used.
- Examples of monovalent amines include aliphatic primary monoamines such as methylamine, ethylamine, propylamine, butylamine, amylamine, octylamine, dodecylamine, stearylamine, and benzylamine, and primary primary amines such as arlin and naphthylamine.
- Monoamines, and alkanol monoamines with primary or secondary amino groups such as secondary monoamines with ⁇ -monoalkyl substitution, ethanolamine, ⁇ -monoalkylethanolamine, and diethanolamine are used. it can.
- modified novolak rosin ( ⁇ ) is further represented by the general formula (8) in the molecule:
- the oxygen atom at the left end is derived from an oxygen atom contained in the aromatic hydroxyl group of the novolak resin, and R 12 represents a hydrogen atom or a methyl group
- an aromatic hydroxyl group May be.
- the modified novolak rosin (A) has both a group represented by the general formula (8) and an aromatic hydroxyl group. Having both of these tends to produce gely wrinkles.
- the number of groups represented by the group represented by the general formula (7), the group represented by the general formula (8), and the aromatic hydroxyl group may be in the range of 0 to 19, respectively. Although there is an effect beyond this range, it is very difficult to control the molecular weight of the novolak resin having a large number of nuclei, and there must be at least one group represented by the general formula (1). In reality, 19 is the upper limit for each. However, the appropriate value varies depending on the type of pigment, the specific surface area and particle diameter of the pigment particles, the presence or absence of pigment surface treatment agent or its properties, the type of thermoplastic resin, the polarity of the dispersion medium, etc. It is preferable to select an optimum value according to the application.
- the modified novolak rosin (A) is further represented by the general formula (9):
- the oxygen atom at the right end is derived from an oxygen atom contained in an aromatic hydroxyl group in the same molecule or different molecules of the novolak resin, and Z has an oxygen atom or a nitrogen atom at the connection end.
- the aromatic hydroxyl group may be replaced with epichlorohydrin or j8.
- -Methylepoxy hydrin is reacted, and then bi- to hexafunctional carboxylic acids, amines (including primary monoamines), or amino acids are reacted.
- basic groups formed by reacting amines and amino acids tend to have an adverse effect on charging characteristics, and therefore it is preferable not to use amines and amino acids. When using amines and amino acids, it is necessary to pay attention to the amount used.
- polyfunctional carboxylic acid examples include succinic acid, maleic acid, itaconic acid, cyclohexanedicarboxylic acid, adipic acid, azelaic acid, sebacic acid, 1,10-decanedicarboxylic acid, dodec-succinic acid , Dimer acid, 3,6-endomethylenetetrahydrophthalic acid, aliphatic polycarboxylic acids such as 3,6-methylendomethylenetetrahydrophthalic acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, Aromatic polycarboxylic acids such as benzophenone tetraforce rubonic acid, ethylene glycol bis trimellitate, glycerol tris trimellitate can be used.
- polyfunctional amines include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, propylenediamine, (dimethylamino) propylamine, (jetylamino) propylamine, hexamethy.
- Examples include aliphatic polyamines such as ethyl) piperazine, xylylenediamine, and dimerdiamine, and aromatic polyamines such as melamine, benzoguanamine, meta-phenylenediamine, and diaminodimethane.
- Polyether diamine, N-aminoethylethanolamine, so-called polyaminoamide, and the like can also be used.
- a crosslinked structure can also be formed by reacting a primary amino group that is bifunctional with an epoxy group.
- the primary monoamine mentioned above can be used.
- Amino acids such as leucine and threonine can also be used.
- an organic solvent is appropriately used as necessary, and a catalyst such as aliphatic tertiary amine, aromatic tertiary amine, or tertiary amine amine salt is used as necessary. It can be carried out by heating to 160 ° C. The progress of the reaction can be followed by measuring the molecular weight by GPC, measuring the epoxy equivalent, and so on.
- the total of the aromatic hydroxyl groups possessed by the modified novolac resin (total of unsubstituted and substituted aromatic hydroxyl groups, and so on) ) Is preferably 20 or less.
- the graft copolymer (B) has the following formula (I):
- V is a monovalent organic group having an oxygen atom or a nitrogen atom at the connecting end and having a carbon number in the range of ⁇ to 20 [wherein general formula (15):
- R 13 and R 14 each independently represents a hydrogen atom or a methyl group).
- R 13 and R 14 each independently represents a hydrogen atom or a methyl group.
- the epoxy group-containing ethylene represented by the general formula (10) The reaction to obtain a monomer represented by the general formula (13) or the general formula (14) by reacting the epoxy group of the polyunsaturated monomer with a hydroxycarboxylic acid and, if necessary, a carboxylic acid amide, If necessary, a solvent can be used, and if necessary, a catalyst such as aliphatic amine, aromatic amine, or ammonium salt can be used and heated to 60 to 160 ° C.
- examples of the halogen atom represented by R 5 include a chlorine atom.
- examples of the hydrocarbon group having 1 to 5 carbon atoms represented by R 6 or R 7 include alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec butyl, t-butyl, and pentyl.
- examples of the alkoxy group having 1 to 5 include, for example, methoxy, butoxy and the like, and examples of the carbon atom having 6 to: L0, such as phenoxy, and examples of the halogen atom include, for example, a fluorine atom, a chlorine atom and a bromine atom. Is mentioned.
- the styrene derivative of the monomer represented by the general formula (11) includes butyltoluene, monomethylstyrene, dimethyls Alkyl-substituted styrenes such as styrene, ethyl styrene, isopropyl styrene, and t-butyl styrene, halogen-substituted styrenes such as chlorostyrene, dichlorostyrene, bromostyrene, and fluorelostyrene, alkoxy-substituted styrenes such as methoxystyrene and butoxystyrene, and phenoxy Aryloxy-substituted styrene such as styrene and 13 chlorostyrene can be used.
- Examples of the monomer represented by the general formula (12) include benzyl (meth) acrylate and phenyl (meth) acrylate.
- Examples of the epoxy group-containing ethylenically unsaturated monomer represented by the general formula (10) include glycidyl (meth) acrylate and 2, 3-epoxy-2-methylpropyl (meth) acrylate. Can be used.
- Examples include butyl ethers having an aliphatic hydroxyl group, and aryl esters of various acids such as allyl acetate.
- the structural unit represented by the general formula (2) in the graft copolymer (B) is derived from the epoxy group-containing ethylenically unsaturated monomer represented by the general formula (10). Although having a unit and an unsaturated bond or a branched structure, it can be obtained from a hydroxycarboxylic acid having 2 to 20 carbon atoms, a mixture thereof, or a polycondensate thereof.
- the general formula (10) It is obtained from an epoxy group-containing ethylenically unsaturated monomer represented by formula (2) and a hydroxycarboxylic acid having 2 to 20 carbon atoms which may have an unsaturated bond or a branched structure, a mixture thereof, or a polycondensate thereof. It is derived from the monomer represented by the general formula (13).
- W 2 and X 2 represent a divalent hydrocarbon group having 1 to 19 carbon atoms which may have an unsaturated bond and Z or a branched structure.
- R 2 and R 3 each independently represent a hydrogen atom or a methyl group.
- the group represented by the formula (wherein X 2 and q are the same as above) is a hydroxycarboxylic acid having 2 to 20 carbon atoms which may have an unsaturated bond and Z or a branched structure , Or a mixture thereof or a polycondensate thereof.
- Examples of the hydroxycarboxylic acid include glycolic acid, lactic acid, oxybutyric acid, hydroxyvaleric acid, hydroxycaproic acid, hydroxycaprylic acid, hydroxycapric acid, hydroxylauric acid, hydroxymyristic acid, hydroxypalmitic acid, ricinoleic acid and castor oil
- Examples thereof include fatty acids and hydrogenated products thereof, 12-hydroxystearic acid and the like.
- a hydroxycarboxylic acid having 12 to 20 carbon atoms particularly preferably ricinoleic acid or castor oil fatty acid having 16 to 20 carbon atoms, and a hydrogenated product thereof
- 12-hydroxystearin Hydroxycarboxylic acids such as acids can be suitably used.
- the number of repetitions p is an integer in the range of 1 to 30, and q is an integer in the range of 0 to 30.
- the appropriate value varies depending on the type of pigment used, the specific surface area and particle diameter of the pigment particles, the nature of the pigment surface treatment agent, the type of thermoplastic resin, the polarity of the dispersion medium, etc. It is necessary to select the optimum value according to the application. In general, p or q ⁇ 2 And p + q ⁇ 2. Even if the value of p or q exceeds the above range, the dispersibility cannot be further improved.
- the formation of the group represented by the general formula (15) or the general formula (17) in the general formula (2) is, for example, by previously synthesizing a polyester by polycondensation of hydroxycarboxylic acid and It can be carried out by a method of reacting a group with the above-mentioned epoxy group, or a method of reacting a carboxyl group of a hydroxycarboxylic acid monomer with the above-mentioned epoxy group and further polycondensing hydroxycarboxylic acid.
- the polycondensation reaction of the hydroxycarboxylic acid is carried out in the presence or absence of a catalyst such as para-toluenesulfonic acid, stannous octylate, dibutyltin diacetate, or tetra-n-butyl titanate.
- a catalyst such as para-toluenesulfonic acid, stannous octylate, dibutyltin diacetate, or tetra-n-butyl titanate.
- the reaction can be carried out while heating and stirring at 180 to 220 ° C. and removing the produced water with an azeotropic solvent such as toluene-xylene.
- the reaction can be followed by molecular weight measurement by GPC or acid value measurement.
- the graft copolymer (B) always has a structural unit represented by the general formula (2) and a structural unit represented by the general formula (3) and Z or the general formula (4). I have to! These contents with respect to the graft copolymer (B) are an amount corresponding to at least 10 mol% of the structural unit represented by the general formula (2) in the graft copolymer, especially an amount corresponding to 10 to 90 mol%. In addition, it is preferable that the constituent unit force represented by the general formula (3) and the general formula (4) is an amount corresponding to at least 10 mol%, particularly 10 to 90 mol%.
- the content corresponding to at least 10 mol% of the structural unit represented by the general formula (2) means that the graft copolymer is divided into structural units derived from the ethylenically unsaturated monomer, Further, it means that the structural unit represented by the general formula (2) contains at least 10 mol%. That is, when the graft copolymer is obtained by copolymerization of n ethylenically unsaturated monomers, the number of structural units represented by the general formula (2) in one molecule of the graft copolymer is at least 0. It means ⁇ ⁇ ⁇ .
- the content of one or more selected from the structural units represented by the general formula (3) and the general formula (4) in an amount corresponding to at least 10 mol% means that the graft polymer is an ethylenically unsaturated monomer.
- the graft copolymer is obtained by copolymerization of n ethylenically unsaturated monomers, from the structural units represented by general formula (3) and general formula (4) in one molecule of the graft copolymer It means that the number of one or more structural units selected is at least 0. ⁇ ⁇ ⁇ .
- Structural Unit Represented by General Formula (2) Structural Unit Represented by General Formula (3) and General Formula (4) Force One of one or more structural units selected, or both forces Predetermined moles If the equivalent amount is not included, sufficient dispersibility cannot be obtained. However, the appropriate value varies depending on the type of pigment, the specific surface area and particle diameter of the pigment particles, the presence or absence of the pigment surface treatment agent, the type of thermoplastic resin, the polarity of the dispersion medium, etc. It is preferable to select the optimum value according to the application.
- the graft copolymer (B) may further have a structural unit represented by the general formula (16).
- the structural unit represented by the general formula (16) is a reaction between an epoxy group of an epoxy group-containing ethylenically unsaturated monomer or copolymer and a monovalent carboxylic acid or a monovalent amine. Can be obtained. Since basic groups formed by reacting monovalent amines tend to adversely affect charging characteristics, it is preferable not to use monovalent amines. When using monovalent amines, it is necessary to pay attention to the amount used.
- monovalent carboxylic acids include saturated fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, strong prillic acid, strong puric acid, lauric acid, myristic acid, palmitic acid, stearic acid, Unsaturated fatty acids such as oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, eleostearic acid, and hydrogenated products thereof can be used.
- saturated fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, strong prillic acid, strong puric acid, lauric acid, myristic acid, palmitic acid, stearic acid, Unsaturated fatty acids such as oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, eleostearic acid, and hydrogenated products thereof can be used.
- Examples of monovalent amines include aliphatic primary monoamines such as methylamine, ethylamine, propylamine, butylamine, amylamine, octylamine, dodecylamine, stearylamine, and benzylamine, and primary primary aromatics such as arlin and naphthylamine.
- Monoamines and secondary monoamines with these N-monoalkyl substitutions, alkanol monoamines with primary or secondary amino groups such as ethanolamine, N-monoalkylethanolamine, diethanolamine, etc. can be used .
- the graft copolymer (B) has the general formula (18): [0113] [Chemical 19]
- R 15 and R 16 each independently represent a hydrogen atom or a methyl group.
- the graft copolymer (B) has a weight average molecular weight of 3,000 to 100,000. If the weight average molecular weight is less than the above range, the dispersibility is sufficient, but it is difficult to adjust the polymerization. On the other hand, if the weight average molecular weight exceeds the above range, sufficient dispersibility tends not to be obtained.
- the amount of the pigment dispersant used is preferably 2 to: L00 parts by mass with respect to 100 parts by mass of the colored chips obtained by heating and kneading the pigment and the thermoplastic resin. More preferably, it is 2 to 50 parts by mass.
- the amount of the pigment dispersant used is less than the above range, the dispersibility and redispersibility tend to be lowered. On the other hand, when it exceeds the above range, the electric resistance value tends to be lowered.
- Examples of this type of charge control agent include fats and oils such as flax oil and soybean oil, alkyd coconut resin, rosin and rosin polymer, aromatic polycarboxylic acid, acid group-containing water-soluble dye, and aromatic polyamine acid. A soot condensate and the like are preferred.
- fats and oils such as flax oil and soybean oil, alkyd coconut resin, rosin and rosin polymer, aromatic polycarboxylic acid, acid group-containing water-soluble dye, and aromatic polyamine acid.
- a soot condensate and the like are preferred.
- charge control agents include cobalt naphthenate, nickel naphthenate, iron naphthenate, zinc naphthenate, zirconium octylate (zirconium octate), conoleate octylate, nickel octylate, zinc octylate, dodecyl.
- Metal salts such as cobalt oxide, nickel dodecylate, zinc dodecylate, cobalt 2-ethylhexylhexanoate, metal sulfonates such as petroleum sulfonates, metal salts of sulfosuccinates, lecithin, kephalin Preferred are phospholipids such as, salicylic acid metal salts such as t-butylsalicylic acid metal complex, polypyrrole pyrrolidone resin, polyamide resin, sulfonic acid group-containing resin, and hydroxybenzoic acid derivatives.
- the color insulation chip obtained by heating and kneading the pigment and the thermoplastic resin is finely pulverized by a wet pulverization method to dissolve the pigment dispersant.
- the type of pulverizer and disperser and the combination of pulverization processes are not particularly limited.
- a simpler manufacturing method that combines both dry grinding and wet grinding of colored chips will be described.
- the pigment and the thermoplastic resin are heat-kneaded with a three-roll mill, a twin-screw extruder, or the like, and after cooling, the resulting colored chips are dry-ground using a dry-type pulverizer.
- the coarsely pulverized product obtained by dry milling preferably has an average particle size of about 7 to 12 ⁇ m. If the kneaded material to be dry-pulverized is soft, for example, if the softening point is 100 ° C or lower, it is cooled, embrittled with liquid nitrogen or solid carbon dioxide, and pulverized.
- the dry grinder for example, a hammer mill, a jet mill, a pin mill, a turbo mill, a cutter mill, a ball mill and the like can be used as appropriate.
- the coarsely pulverized product obtained by the dry pulverization is selected from at least a group force consisting of the modified novolac rosin (A) and the graft copolymer (B).
- the liquid developer of the present invention can be obtained by wet pulverization in an electrically insulating hydrocarbon solvent in which one kind of pigment dispersant is dissolved.
- the charge adjusting agent that can be added to the liquid developer as necessary is added during wet pulverization and / or after wet pulverization. You can.
- wet pulverizer examples include media-type dispersers such as Eiger mill, attritor, sand mill, dyno mill, ball mill, DCP mill, apex mill, pearl mill, Ultimizer 1 (manufactured by Sugino Machine Co., Ltd.), Nanomizer 1 (Nanomizer 1 Medialess pulverizers such as a maker full mouth diizer (made by Mizuho Industry Co., Ltd.) and DeBee2000 (made by DeBee) can be used as appropriate.
- the toner particles in the liquid developer obtained by wet pulverization preferably have an average particle diameter of 0.1 to 5 / ⁇ ⁇ , more preferably 0.1, from the viewpoint of obtaining a high-definition image. ⁇ 3 ⁇ m.
- the liquid developer obtained from the above materials and production method is a liquid developer capable of high solid content and excellent in developability.
- the solid content concentration in the liquid developer is targeted for all solid components including pulverized colored chips (ie, toner particles), pigment dispersant, and other solid contents.
- pulverized colored chips ie, toner particles
- pigment dispersant ie, toner particles
- the solid content concentration in the liquid developer is targeted for all solid components including pulverized colored chips (ie, toner particles), pigment dispersant, and other solid contents.
- it is 13-50 mass%.
- good fluidity and developability can be maintained until the solids concentration reaches 50% by weight using a wet-grinding method for colored chips, which is difficult to maintain dispersion stability and charging characteristics. In this respect, it can be said that it is extremely high and has an operational effect that has never been seen before.
- Pigment Blue 15 3 (Daiichi Seika Kogyo Co., Ltd.)
- Solsperse 17000 (manufactured by Avecia) was used as a comparative pigment dispersant.
- Epoxy rosin (AER6064, manufactured by Asahi Kasei Corporation) was used.
- Pigment Blue 15 3 250 parts and thermoplastic rosin 1 750 parts using a three-heat roll at 140 ° C. After cooling the kneaded meat (colored chips), The mixture was pulverized using a jet mill (Nihon-Eumatic Co., Ltd.). Next, 140 parts of this coarsely pulverized product, a pigment dispersant 1 of 8.8 parts, high-boiling paraffinic solvent (Molesco White P-40) 555.1 Using an Eiger mill (trade name M-250) filled with 2 parts of 0.5 mm diameter zirca beads 40 Liquid developer 1 having a solid content of 21.3% was obtained by wet pulverization for about 90 minutes at ° C.
- Pigment Blue 15 3 250 parts and thermoplastic rosin 1 750 parts using a three-heat roll at 140 ° C. After cooling the kneaded meat (colored chips), The mixture was pulverized using a jet mill (Nihon-Eumatic Co., Ltd.). Next, 140 parts of this coarsely pulverized product, 5.3 parts of Pigment Dispersant 1 and 554.7 parts of high-boiling paraffinic solvent (Molesco White P-40) were filled with Zirca beads with a diameter of 0.5 mm. (Trade name M-250) was used for wet milling at a temperature of 40 ° C. for about 90 minutes to obtain a liquid developer 2 having a solid content concentration of 20.8% by weight.
- Pigment Blue 15 3 and 667 parts of thermoplastic resin 1 were melted and kneaded at 140 ° C using three hot rolls at 140 ° C. The mixture was pulverized using a jet mill (Nihon-Eumatic Co., Ltd.). Next, 210 parts of this coarsely pulverized product, 5.3 parts of Pigment Dispersant 1 and 484.7 parts of high-boiling paraffinic solvent (Molesco White P-40) were filled with 0.5 mm diameter zirconia beads. (Product name M-250) was wet-ground for about 90 minutes at a temperature of 40 ° C. to obtain Liquid Developer 3 having a solid content concentration of 30.8%.
- Pigment Blue 15 3 250 parts and thermoplastic rosin 1 750 parts using a three-heat roll at 140 ° C. After cooling the kneaded meat (colored chips), The mixture was pulverized using a jet mill (Nihon-Eumatic Co., Ltd.). Next, 140 parts of this pulverized product, 8.8 parts of Pigment Dispersant 2 and 551.2 parts of high-boiling paraffinic solvent (Molesco White P-40) were filled with 0.5 mm diameter zirconia beads (Eiger Mill). Using a product name M-250), wet pulverization was carried out at a temperature of 40 ° C. for about 90 minutes to obtain a liquid developer 4 having a solid concentration of 21.3%.
- thermoplastic resin 2 instead of thermoplastic resin 1 and high-boiling paraffinic solvent (IP Solvent 2835) instead of high-boiling paraffinic solvent (Molecocote P-40), the same as Example 1.
- IP Solvent 2835 high-boiling paraffinic solvent
- Molecocote P-40 high-boiling paraffinic solvent
- Pigment Blue 15 3 250 parts and thermoplastic rosin 1 750 parts using a three-heat roll at 140 ° C. After cooling the kneaded meat (colored chips), The mixture was pulverized using a jet mill (Nihon-Eumatic Co., Ltd.). Next, 140 parts of this coarsely pulverized product and 560 parts of a high-boiling paraffin solvent (Molesco White P-40) were filled in with Eiger mill (trade name M-250) filled with 0.5 mm diameter Zircoyu beads. Liquid developer 6 having a solid content concentration of 20% was obtained by wet pulverization at 40 ° C for about 90 minutes.
- Pigment Blue 15 3 250 parts and thermoplastic rosin 1 750 parts using a three-heat roll at 140 ° C. After cooling the kneaded meat (colored chips), The mixture was pulverized using a jet mill (Nihon-Eumatic Co., Ltd.). Next, 140 parts of this coarsely pulverized product, 8.8 parts of Solsperse 17000 (manufactured by Avecia) and 551.2 parts of high-boiling paraffinic solvent (Molesco White P-40) are filled with zirconia beads having a diameter of 0.5 mm. Was subjected to wet grinding for about 90 minutes at a temperature of 40 ° C. using an Eiger mill (trade name M-2 50) to obtain a liquid developer 7 having a solid content concentration of 21.3%.
- Viscosity of liquid developer at 25 ° C is changed to E type viscometer (with viscosity in the range of lOmPa 's or more and less than lOOmPa s! /, In the range exceeding lOOmPa Measured at 5 rpm) and measured as the viscosity after 60 seconds.
- the liquid developer of Comparative Example 1 had a high viscosity and was unable to be measured.
- the electrical resistance value of the liquid developer (whose viscosity could be measured) was measured by R83 4 manufactured by Advance Co.
- the toner particle size range is measured with an optical microscope (manufactured by Olympus Corporation). It was measured visually.
- a colored chip obtained by heating and kneading a pigment and a thermoplastic resin is used with a specific pigment dispersant having an aromatic ring and an epoxy group ring-opening structure based on a carboxyl group derived from hydroxycarboxylic acid.
- the liquid developer obtained by wet pulverization can be highly solid-differentiated with a low viscosity despite the wet pulverization method, and further has good developability with a high electrical resistance value.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Liquid Developers In Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
Claims
Priority Applications (5)
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CA002609825A CA2609825A1 (en) | 2005-05-26 | 2006-05-24 | Liquid developing agent and process for producing the same |
EP06756517A EP1884834A1 (en) | 2005-05-26 | 2006-05-24 | Liquid developing agent and process for producing the same |
AU2006250500A AU2006250500A1 (en) | 2005-05-26 | 2006-05-24 | Liquid developing agent and process for producing the same |
US11/915,422 US20100062361A1 (en) | 2005-06-08 | 2006-05-24 | Liquid developing agent and process for producing the same |
JP2007517850A JP5175547B2 (ja) | 2005-05-26 | 2006-05-24 | 液体現像剤およびその製造方法 |
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JP2005154073 | 2005-05-26 | ||
JP2005-154073 | 2005-05-26 |
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WO2006126566A1 true WO2006126566A1 (ja) | 2006-11-30 |
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PCT/JP2006/310311 WO2006126566A1 (ja) | 2005-05-26 | 2006-05-24 | 液体現像剤およびその製造方法 |
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EP (1) | EP1884834A1 (ja) |
JP (1) | JP5175547B2 (ja) |
KR (1) | KR20080018869A (ja) |
CN (1) | CN101185039A (ja) |
AU (1) | AU2006250500A1 (ja) |
CA (1) | CA2609825A1 (ja) |
WO (1) | WO2006126566A1 (ja) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101558054B (zh) * | 2006-12-15 | 2014-11-19 | 富士胶片株式会社 | 光学膜、延迟板和液晶化合物 |
WO2015079979A1 (ja) | 2013-11-28 | 2015-06-04 | キヤノン株式会社 | 紫外線硬化型液体現像剤 |
DE102016109775A1 (de) | 2015-05-27 | 2016-12-01 | Canon Kabushiki Kaisha | Flüssigentwickler |
EP3151067A1 (en) | 2015-09-30 | 2017-04-05 | Canon Kabushiki Kaisha | Curable liquid developer |
US9891546B2 (en) | 2015-05-27 | 2018-02-13 | Canon Kabushiki Kaisha | Ultraviolet-curable liquid developer |
US9891547B2 (en) | 2015-05-27 | 2018-02-13 | Canon Kabushiki Kaisha | Ultraviolet-curable liquid developer |
EP3410217A1 (en) | 2017-05-31 | 2018-12-05 | Canon Kabushiki Kaisha | Curable liquid developer and method for producing curable liquid developer |
US10162281B2 (en) | 2016-06-27 | 2018-12-25 | Canon Kabushiki Kaisha | Liquid developer and manufacturing method of liquid developer |
US10175597B2 (en) | 2015-05-27 | 2019-01-08 | Canon Kabushiki Kaisha | Liquid developer and method of producing same |
US10372053B2 (en) | 2015-05-27 | 2019-08-06 | Canon Kabushiki Kaisha | Recorded material and image forming method |
US10423084B2 (en) | 2017-11-20 | 2019-09-24 | Canon Kabushiki Kaisha | Method for producing liquid developer |
US10545424B2 (en) | 2017-09-28 | 2020-01-28 | Canon Kabushiki Kaisha | Liquid developer and method of producing liquid developer |
DE112018004321T5 (de) | 2017-09-28 | 2020-05-20 | Canon Kabushiki Kaisha | Flüssigentwickler und Verfahren zu dessen Herstellung |
US11188005B2 (en) | 2019-09-26 | 2021-11-30 | Canon Kabushiki Kaisha | Liquid developer |
US11281120B2 (en) | 2019-05-30 | 2022-03-22 | Canon Kabushiki Kaisha | Liquid developer and image-forming method |
US11624987B2 (en) | 2018-03-16 | 2023-04-11 | Canon Kabushiki Kaisha | Liquid developer |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5103504B2 (ja) * | 2010-05-27 | 2012-12-19 | 京セラドキュメントソリューションズ株式会社 | 液体現像剤及び湿式画像形成方法 |
US9395638B2 (en) * | 2011-12-19 | 2016-07-19 | Hewlett-Packard Indigo B.V. | Liquid electrophotographic inks |
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2006
- 2006-05-24 WO PCT/JP2006/310311 patent/WO2006126566A1/ja active Application Filing
- 2006-05-24 EP EP06756517A patent/EP1884834A1/en not_active Withdrawn
- 2006-05-24 JP JP2007517850A patent/JP5175547B2/ja not_active Expired - Fee Related
- 2006-05-24 CA CA002609825A patent/CA2609825A1/en not_active Abandoned
- 2006-05-24 CN CNA2006800184723A patent/CN101185039A/zh active Pending
- 2006-05-24 KR KR1020077026956A patent/KR20080018869A/ko not_active Application Discontinuation
- 2006-05-24 AU AU2006250500A patent/AU2006250500A1/en not_active Abandoned
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JPH03188469A (ja) * | 1989-09-28 | 1991-08-16 | Fuji Photo Film Co Ltd | 非水系分散剤および静電写真用液体現像剤 |
JPH0485551A (ja) * | 1990-07-30 | 1992-03-18 | Fuji Photo Film Co Ltd | 非水系分散剤および静電写真用液体現像剤 |
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Cited By (19)
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CN101558054B (zh) * | 2006-12-15 | 2014-11-19 | 富士胶片株式会社 | 光学膜、延迟板和液晶化合物 |
WO2015079979A1 (ja) | 2013-11-28 | 2015-06-04 | キヤノン株式会社 | 紫外線硬化型液体現像剤 |
US10372053B2 (en) | 2015-05-27 | 2019-08-06 | Canon Kabushiki Kaisha | Recorded material and image forming method |
DE102016109775A1 (de) | 2015-05-27 | 2016-12-01 | Canon Kabushiki Kaisha | Flüssigentwickler |
US9798265B2 (en) | 2015-05-27 | 2017-10-24 | Canon Kabushiki Kaisha | Liquid developer |
US9891546B2 (en) | 2015-05-27 | 2018-02-13 | Canon Kabushiki Kaisha | Ultraviolet-curable liquid developer |
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US10175597B2 (en) | 2015-05-27 | 2019-01-08 | Canon Kabushiki Kaisha | Liquid developer and method of producing same |
EP3151067A1 (en) | 2015-09-30 | 2017-04-05 | Canon Kabushiki Kaisha | Curable liquid developer |
US9971268B2 (en) | 2015-09-30 | 2018-05-15 | Canon Kabushiki Kaisha | Curable liquid developer having a cationically polymerizable liquid monomer with a monofunctional vinyl ether compound |
US10162281B2 (en) | 2016-06-27 | 2018-12-25 | Canon Kabushiki Kaisha | Liquid developer and manufacturing method of liquid developer |
EP3410217A1 (en) | 2017-05-31 | 2018-12-05 | Canon Kabushiki Kaisha | Curable liquid developer and method for producing curable liquid developer |
US10545424B2 (en) | 2017-09-28 | 2020-01-28 | Canon Kabushiki Kaisha | Liquid developer and method of producing liquid developer |
DE112018004321T5 (de) | 2017-09-28 | 2020-05-20 | Canon Kabushiki Kaisha | Flüssigentwickler und Verfahren zu dessen Herstellung |
US11513448B2 (en) | 2017-09-28 | 2022-11-29 | Canon Kabushiki Kaisha | Liquid developer and method for manufacturing liquid developer |
US10423084B2 (en) | 2017-11-20 | 2019-09-24 | Canon Kabushiki Kaisha | Method for producing liquid developer |
US11624987B2 (en) | 2018-03-16 | 2023-04-11 | Canon Kabushiki Kaisha | Liquid developer |
US11281120B2 (en) | 2019-05-30 | 2022-03-22 | Canon Kabushiki Kaisha | Liquid developer and image-forming method |
US11188005B2 (en) | 2019-09-26 | 2021-11-30 | Canon Kabushiki Kaisha | Liquid developer |
Also Published As
Publication number | Publication date |
---|---|
EP1884834A1 (en) | 2008-02-06 |
AU2006250500A1 (en) | 2006-11-30 |
JP5175547B2 (ja) | 2013-04-03 |
CN101185039A (zh) | 2008-05-21 |
JPWO2006126566A1 (ja) | 2008-12-25 |
KR20080018869A (ko) | 2008-02-28 |
CA2609825A1 (en) | 2006-11-30 |
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