WO1990010893A1 - Composition d'un toner electrophotographique - Google Patents

Composition d'un toner electrophotographique Download PDF

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Publication number
WO1990010893A1
WO1990010893A1 PCT/JP1990/000305 JP9000305W WO9010893A1 WO 1990010893 A1 WO1990010893 A1 WO 1990010893A1 JP 9000305 W JP9000305 W JP 9000305W WO 9010893 A1 WO9010893 A1 WO 9010893A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyester resin
acid
toner
resin
toner composition
Prior art date
Application number
PCT/JP1990/000305
Other languages
English (en)
Japanese (ja)
Inventor
Nobuo Yamada
Hiroyuki Kamigaki
Fujio Tsutsui
Hisato Miyagawa
Original Assignee
Arakawa Kagaku Kogyo Kabushiki Kaisha
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Arakawa Kagaku Kogyo Kabushiki Kaisha filed Critical Arakawa Kagaku Kogyo Kabushiki Kaisha
Priority to DE19904090368 priority Critical patent/DE4090368T1/de
Publication of WO1990010893A1 publication Critical patent/WO1990010893A1/fr
Priority to GB9024263A priority patent/GB2237399A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
    • C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/087—Binders for toner particles
    • G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08755—Polyesters

Definitions

  • the present invention relates to a toner composition for electrophotography. More specifically, the binder contains a low acid value polyester resin obtained by modifying a normal polyester resin with a specific modifier as a binder.
  • the present invention relates to an electrophotographic toner composition having excellent environmental characteristics. Background art
  • electrophotographic toners have been required to have not only thermal characteristics such as low-temperature fixing, offset resistance, and in-j pi-tuning property but also electrostatic stability.
  • styrene-acrylic copolymers have been widely used as a binder that satisfies these characteristics to some extent.
  • the present inventors focused on the type of etherified bisphenol, which is a raw material used for the polyester resin.
  • Japanese Patent Application Laid-Open No. 61-86670 discloses a polyester resin obtained by modifying a specific polyester resin with a polysocyanate compound. Although it is described that it is good as a binder, it is possible to point out disadvantages in practicing the invention. .
  • the base polyester resin used as a toner binder has a relatively large molecular weight and a large glass transition point, so the melt viscosities are relatively large.
  • the polyisocyanate compound is not uniformly mixed with the base polyester resin, and the reaction tends to be non-uniform.
  • the polyisocyanate compound hardly reacts with the residual carboxyl group in the polyester resin, so that it exhibits satisfactory environmental properties as a result. No binder resin is available.
  • the present inventors modified the polyester resin itself to obtain low-temperature fixing property, offset resistance, and anti-blowing property.
  • the purpose is to develop a polyester electrophotographic toner having significantly improved environmental characteristics without deteriorating the packing property.
  • Intensive studies were made, especially on the acid value of binder resin.
  • the object of the present invention can be achieved by using a low acid value polyester resin that has been modified with a specific modifier. And completed the present invention.
  • the present invention relates to an electrophotographic toner in which a colorant is dispersed in a binder resin, wherein the binder resin has a polyester having an acid value of 5 to 50. And a dalycidyl compound having at least one glycidyl group that reacts with the remaining carboxyl groups of the polyester resin.
  • the present invention relates to an electrophotographic toner composition characterized by being a polyester resin having an acid value of less than 5 reacted.
  • a polyester resin having an acid value of 5 to 50 (hereinafter referred to as a base polyester resin) and Denaturant
  • the use of low-acid-value polyester resin obtained by reacting a specific glycidyl compound used as a binder resin Is required.
  • the base polyester resin is composed of an acid component and a polyhydric alcohol component.
  • the acid component phenolic acid, dicarboxylic acid, tribasic or higher polybasic acid and the like are used.
  • the monocarboxylic acids include, for example, palmitic acid, stearic acid, benzoic acid, black benzoic acid, dicyclo benzoic acid, and paratauric acid. -Such as benzoyl carboxylate, cyclohexan carbonic acid, tonole olenoic acid, and rosins, etc. Taking into account the softening point, cost, etc. of the binder resin, benzoic acid, para-butyl benzoic acid, and rosins are preferred. Since monocarboxylic acids have a great effect of improving the low-temperature fixability of the obtained toner, they can be selected and used as desired. .
  • the amount of the monocarboxylic acids to be used is set to not more than about 40 mol% in the acid components. If the amount of force used exceeds 40 mol%, either the base polyester resin or the denatured polyester resin may be used.
  • the glass transition point (hereinafter, referred to as Tg) is also extremely low, and the blocking resistance of the toner tends to decrease.
  • Dicarboxylic acids are essential acid components, for example, orthophthalic acid, isofluric acid, terephthalanolic acid, and endmethylentrate.
  • the following are examples of the acid, sebacic acid, dimer acid, and these lower alkyl esters and acid anhydrides.
  • the amount of the dicarboxylic acid used is usually about 40 to 100 mol%, preferably 50 to; L 00 mono%, based on the total acid component. .
  • tribasic or higher polybasic acids such as trimellitic acid, pyromellitic acid, or anhydrides of these acids.
  • the polybasic acid appropriately adjusts the crosslink density of the obtained base polyester resin, the offset resistance is remarkably improved.
  • the amount used is usually about 30 mol% or less of the total acid component.
  • polyvalent alcohol component of the base polyester resin there are no particular restrictions on the polyvalent alcohol component of the base polyester resin, and the following various types may be appropriately selected and used. Specific examples include ethylene glycol, ethylene glycol, triethylene glycol, propylene, and so on. 1,4-butanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexadiol, 1,2-butanediol, 1,3-butanediol For example, it can be used to produce diols, polyester diphenols, logging glycerol phenols, hydrogenated bisphenols, etc. For example, glycerin, trimethic acid, tri-methyl methacrylate, chlorophyll, etc.
  • the acid component and the polyhydric alcohol component are simultaneously or appropriately divided. And then prepare, for example, dibutyl
  • the method include a method of producing by performing a heat reaction in the presence or absence of a reaction catalyst such as an organic tin compound such as suzuxide.
  • the desired base polyester resin can be obtained regardless of the presence or absence of the solvent, but the water produced during the reaction can be removed.
  • a solvent such as toluene, xylene, or the like may be used to distill off the system outside the system.
  • the reaction temperature and time are appropriately determined in consideration of the yield and constant number of the product, and usually may be 1 to 20 hours at 150 to 300 ° C. If a solvent is used during the reaction, a solid resin can be obtained by distilling off the solvent under reduced pressure.
  • the end point of the reaction is determined by measuring the acid value of the resin formed, the content of the insoluble component in the solvent, the gel permeation chromatogram or the softening point, etc. It may be determined as appropriate.
  • the physical and chemical constants of the base polyester resin are determined in consideration of the properties of the binder-resin finally produced according to the present invention obtained by the subsequent denaturation reaction. I have to do it.
  • the softening point of this material is preferably 70 to 180 ° C, and if the softening point exceeds 180 ° C. In some cases, the low-temperature fixability is reduced, and in the case of 7 (TC), there is a disadvantage in that the offset resistance is reduced.
  • the T g of the polyester resin is preferably 50 to 85. C. It is preferable that the T g be below 50 ° C if the T g is less than 50 ° C.
  • the base polyester resin is a tetrahydropropane resin. Not only those that completely dissolve in the run, but also those that contain up to about 80% of the insoluble content in the solvent can be used.
  • Es The acid value of the resin is determined by the subsequent modification so that the acid value of the modified resin is less than 5, preferably 4 or less. Although there is no particular limitation, it is usually preferable to be about 5 to 50 in view of the relationship with the molecular weight. Also, the hydroxyl value is preferably 50 or less.
  • the base polyester resin obtained above is reacted with a specific glycidyl compound.
  • the modifying agent used in the present invention contains at least one daricidyl group in the molecule that can react with the residual carboxyl group of the base polyester resin.
  • a compound having at least one glycidyl ester group in the molecule which is a glycidyl compound (hereinafter referred to as a denaturant).
  • Compounds with at least one siglyetheryl group in the molecule compounds with at least one glycidylamino group in the molecule
  • styrene-acrylic copolymers which are composed of glyceryl (meta) acrylate as a constituent monomer.
  • Examples of the compound having at least one of the above-mentioned glycidyl ester groups in the molecule include glycidyl ester acetate and laurin acetate.
  • Resin acid monoglycidyl ester, luster, fluoric acid jig Polyvalent glycidyl esters such as diglycidyl ester and dimer diglycidyl ester; It is possible to increase the power of the Grease Creator, Grease Creator, etc.
  • the rosin used in the logging reseal ester includes gamlogin, paddling, and trolling oil. In addition, it is possible to demonstrate these hydrides, disproportionates, etc.
  • the compound having at least one of the above-mentioned glycidyl ether groups in the molecule is, for example, n-butyl glycidyl ether. , Ary glycidyl ether, 2-ethyl hexyl ether, octyl glycidyl ether, phenyl glycidyl ether, phenyl ⁇ ⁇ ⁇ ⁇ p p p p p p p p p ⁇ ⁇ p p p ⁇ ⁇ ⁇ ⁇ p p p p-p p p — — — —.
  • a compound having at least one glycidylamino group in a molecule is, for example, a diglycidylanilint. Registrar, Nutrimetal, Tetra-glu-Zi-Amino-Ji-N-O-M The diamin etc. are exposed. , And in a styrene-acrylic copolymer in which the glycidyl (meta) acrylate is a constituent, Monomers to be used in addition to the acrylate (meta) acrylates include styrene, na-methyl styrene, and phenolic groups.
  • the content of glycidyl (meta) acrylate in the copolymer is not particularly limited, but is usually about 0.1 to 50 mol%. .
  • the molecular weight of or copolymer 1 0 3 ⁇ ; L 0 6 about, Sw Z ⁇ is that you and 2-6 0 about not to good or. There are no particular restrictions on the polymerization method, and various polymerization methods may be applied.
  • the Tg of the resulting modified polyester resin fluctuates depending on the type and amount of the modifying agent used, and in many cases, there is a tendency for a considerable decrease in the Tg.
  • the strength of maintaining the toner's anti-blocking properties, and particularly, the use of a logging glycidyl ester as a denaturant is preferred. Use it well.
  • the strong resiliency ester has a modified polystyrene due to its bulky alicyclic structure, which is a lipo-functional skeleton. Since the T g of the ester resin is hardly reduced, it is possible to easily produce a polyester resin having a desired constant, and this is possible. There is an advantage in that the degree of freedom in changing is increased.
  • the base polyester resin and the modifying agent are charged at a predetermined ratio, respectively, and a reflux solvent such as toluene or xylene is charged. In the presence or absence of water, the mixture is usually stirred and heated at 100 to S0 ° C for about 1 to 30 hours.
  • the amount of the denaturing agent used depends on the acid value of the base polyester resin, the type of denaturing agent, its epoxy equivalent weight, its reactivity, and the denaturing polyester. It may be appropriately determined in consideration of the target acid value of the resin, and the like. Further, the determination of the end point of the denaturation reaction is performed by: Make sure that the acid value has reached the target range.
  • the acid value is determined by sufficiently dissolving or swelling 1 g of the polyester resin in 50 ml of tetrahydrofuran and then 1/1/10 NK 0H- It is measured using a solution of phenol and phenol phthalate as an indicator.
  • the acid value of the modified polyester resin obtained must be carefully determined to have a significant effect on the environmental properties of the toner, and In the invention it should be less than 5, preferably less than 4. If the acid value is 5 or more, the difference between the charge of the obtained toner under low temperature and low humidity and the charge under high temperature and high humidity is large. It is not preferable because image stability is reduced.
  • the modified polyester resin has a high molecular weight. Even if it does not dissolve in a solvent with low polarity such as toluene, use it without any change.
  • the Tg is usually in the range of 50 to 85 ° C.
  • a modified polyester resin having an acid value of less than 5, preferably 4 or less as a binder resin in the present invention can be easily obtained. be able to .
  • the toner can be obtained by dispersing the colorant in the binder resin.
  • a conventionally known colorant may be used as it is.
  • Examples include carbon black, cinnamon blue dye, aniline blue, calco oinole blue, chrom yellow. ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Green Oxalate, Lamp Black, Rose Bengal, Monastranola Red
  • the power is increased.
  • the content of the coloring agent in the toner is preferably 0.1 to 30% by weight, preferably 0.2 to 20% by weight. When the content is less than 0.1% by weight, the toner image density after fixing tends to be low, and when the content exceeds 30% by weight, the binder resin is blended. This tends to make it difficult for the effect of the present invention to be exhibited.
  • the toner composition of the present invention using the modified polyester resin as a binder resin is produced by appropriately mixing various additives with the toner. It is done.
  • the toner of the present invention may optionally further contain a carrier such as a magnetic substance.
  • a carrier such as a magnetic substance.
  • magnetic substances include, for example, metal powders such as iron, manganese, nickel, konokoretto, chromium, ferrite, and magnesium. It can remove iron alloys such as genites, alloys or compounds such as cobalt, nickel and manganese, and other known ferromagnetic materials.
  • a reactive dye for example, a reactive dye, an organic polyvalent metal compound, a wax, and a charge control agent may be blended.
  • the acid value, Tg, and softening point of the obtained modified polyester resin were 0.863 and 140, respectively, in that order. Note that Tg is represented by the temperature at which the peak top is measured by the DSC method, and the softening point is represented by the temperature at the time of 4 mm penetration measured by a flote tester. did.
  • the charge amount was measured in the same manner as described above, except that the temperature in the constant temperature chamber was 30 ° C and the relative humidity was 85%.
  • the charge retention was calculated by the following equation. Table 3 shows the results.
  • Example 2 The base polyester resin obtained in (1) of Example 1 was used. The reaction was carried out in the same manner as in Example 1 except that the denaturing agent was used and the type of denaturing agent was changed as shown in Table 2 to obtain the desired denatured polyester. Obtained resin. Table 2 shows various constants of the modified polyester resin. Toner was prepared in the same manner as in Example 1, (2) except that the resin was used. The environmental characteristics and physical properties of this toner were measured in the same manner as in Example 1. The results are shown in Tables 3 and 4.
  • Example 1 the acid component, the polyhydric alcohol component, and the amount of each of them were changed as shown in Table 1 for at least one of them.
  • the same reaction was carried out to obtain various base polyester resins, and the acid value and Tg of these base polyester resins were determined in Examples. It was measured in the same way as 1. Table 1 shows the results.
  • Example 1 When the toner is toned, the modified polyester resin obtained above is used, and the toner is formed in the same manner as in Example 1, (2). It was prepared. The environmental properties and physical properties of these toners were measured in the same manner as in Example 1. The results are shown in Tables 3 and 4.
  • Examples 8 and 9 Various types of toners were prepared using the modified polyester resin obtained in Example 5 and changing the amount of the toners as shown in Table 3. The environmental and physical properties of these toners were measured in the same manner as in Example 1. The results are shown in Tables 3 and 4. '
  • Example 1 the reaction was carried out in the same manner as in Example 1 except that the types of raw materials used and the amounts of the raw materials used were changed as shown in Tables 1 and 2, and the reaction was carried out. Ester resin was obtained. Example of toner preparation and measurement of its environmental and physical properties
  • Tables 3 and 4 show the measurement results of the environmental characteristics and physical properties of the toner.
  • Toner was prepared using the base polyester resin obtained in Example 1 (1) as it was, and in the same manner as in Example 1, to prepare a toner.
  • the environmental and physical properties of the selected toner were measured. The results are shown in Tables 3 and 4.
  • Example 1 the reaction was carried out in the same manner except that the polyalcohol component of the polyester resin was changed. A resin was obtained. Then, a toner was prepared in the same manner as in Example 1 except that the base polyester resin was used, and the environmental characteristics and physical properties of the obtained toner were obtained. Properties were measured. The sorghum is shown in Tables 3 and 4. Comparative Examples 3 and 4
  • the base polyester tree J3 obtained in (1) of Example 1 was used as it was, and the toner composition was changed as shown in Table 3. Otherwise, the toner was set in the same manner as in Example 1. After preparation, the environmental properties and physical properties of the toner were measured. The results are shown in Tables 3 and 4.
  • Example 1 'Except that the base polyester resin obtained in (1) of Example 1 was used as it was, and the amount of the modifier used was changed as shown in Table 2, By a denaturation reaction in the same manner as in Example 1, a modified polyester resin was obtained. Toner was prepared in the same manner as in Example 1, (2) except that the resin was used instead of the resin. The environmental properties and physical properties of the obtained toner were measured in the same manner as in Example 1. The results are shown in Tables 3 and 4.
  • each of the toners in each of the examples in which the binder resin was used as the modified polyester resin in the present invention is not limited to this, while it exhibited good environmental characteristics.
  • the toner composition of the present invention shows that the low-temperature adhesion property, the offset resistance and the blocking resistance do not decrease. ⁇ Power, ru.
  • TPA terephthalic acid
  • DMT dimethyl terephthalate
  • 1PA isophthalic acid
  • AZA azelaic acid
  • ⁇ trimellitic anhydride
  • RGE rosindaricidyl ester
  • EG ethylene glycol
  • P0 poly-polypropylene (2,2) -Bis (4-hydroxyphenyl) propane
  • E0 Polyoxyethylene (2,2) -bis (4-hydroxyphenyl) propane: The results are shown in Table 2.
  • Polyester glycidyl of modified polyester resin Glycidyl glycidyl GMA-containing acid value Tg of ter resin
  • Example 5 RGB 0.056 1.5 135 64 6
  • Example 6 RGE 0.054 2.0 162 66
  • Example 7 RGE 0.004 Epico '2.8 168 72
  • Epiko 1001 Bisphenol A type epoxy resin (manufactured by Shell Chemical Co., Ltd.)
  • the molecule 3 ⁇ 4 is 3600 and the softening point is i) 5 ° C.
  • a specific polyester resin having a low acid value is used as a binder resin.
  • it is possible to completely solve problems that could not be sufficiently solved by the conventional technology. In other words, it impairs the offset resistance, blocking resistance, and low-temperature fixability, which are the required performances of the toner composition for electrophotography.
  • the toner composition of the present invention is suitably used particularly as an electrophotographic toner composition for a high-speed copying machine and a full-color copying machine. This has the effect of Industrial applicability
  • the toner composition for electrophotography of the present invention has an environmental property higher than that of the conventional one while maintaining appropriate offset resistance, blocking resistance, and low-temperature fixing property. Since it has been significantly improved, it can be suitably used as a toner composition for electrophotography, particularly for high-speed copying machines and full-color copying machines.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Composition d'un toner électrophotographique comprenant un colorant dispersé dans une résine servant de liant, caractérisé en ce que ladite résine se compose d'une résine de polyester d'une valeur d'acidité inférieure à 5 préparée par la réaction d'une résine de polyester de départ d'une valeur d'acidité comprise entre 5 et 50 avec un composé glycidylique comportant au moins un groupe glycidyle pouvant réagir avec les groupes carboxyle restants de ladite résine de polyester. Ce toner présente une amélioration remarquable de ses caractéristiques par rapport à l'environnement, tout en conservant une résistance modérée au déport, une résistance au blocage et une aptitude au fixage à basse température, ce qui permet de l'utiliser avantageusement en tant que toner électrophotographique aussi bien dans des copieurs à grande vitesse que dans des copieurs panchromatiques.
PCT/JP1990/000305 1989-03-10 1990-03-08 Composition d'un toner electrophotographique WO1990010893A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19904090368 DE4090368T1 (de) 1989-03-10 1990-03-08 Elektrophotographische tonerzusammensetzung
GB9024263A GB2237399A (en) 1989-03-10 1990-11-08 Electrophotographic toner composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1/64054 1989-03-10
JP6405489 1989-03-10

Publications (1)

Publication Number Publication Date
WO1990010893A1 true WO1990010893A1 (fr) 1990-09-20

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PCT/JP1990/000305 WO1990010893A1 (fr) 1989-03-10 1990-03-08 Composition d'un toner electrophotographique

Country Status (2)

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GB (1) GB2237399A (fr)
WO (1) WO1990010893A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0469752A1 (fr) * 1990-07-30 1992-02-05 MITSUI TOATSU CHEMICALS, Inc. Liant pour toner sec
EP1480089A1 (fr) * 2002-02-28 2004-11-24 Sanyo Chemical Industries, Ltd. Liants de toner

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5368970A (en) * 1993-12-06 1994-11-29 Xerox Corporation Toner compositions with compatibilizer
CN1119706C (zh) * 1994-07-22 2003-08-27 株式会社东芝 带正电单组分调色剂及其显象方法
US6248493B1 (en) * 1998-09-25 2001-06-19 Dainippon Ink And Chemicals, Inc. Toner for non-magnetic single component development
US6238836B1 (en) * 1998-09-25 2001-05-29 Dainippon Ink Chemicals, Inc. Toner composition and developer for electrostatic image development

Citations (4)

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Publication number Priority date Publication date Assignee Title
JPS59159173A (ja) * 1983-03-01 1984-09-08 Mitsui Toatsu Chem Inc 乾式トナ−
JPS6090344A (ja) * 1983-10-25 1985-05-21 Canon Inc 電子写真用トナ−
JPS62215962A (ja) * 1986-03-18 1987-09-22 Dainippon Ink & Chem Inc 静電荷像現像用トナ−
JPS62226161A (ja) * 1986-03-26 1987-10-05 Arakawa Chem Ind Co Ltd 低温定着性に優れた電子写真用トナ−組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59159173A (ja) * 1983-03-01 1984-09-08 Mitsui Toatsu Chem Inc 乾式トナ−
JPS6090344A (ja) * 1983-10-25 1985-05-21 Canon Inc 電子写真用トナ−
JPS62215962A (ja) * 1986-03-18 1987-09-22 Dainippon Ink & Chem Inc 静電荷像現像用トナ−
JPS62226161A (ja) * 1986-03-26 1987-10-05 Arakawa Chem Ind Co Ltd 低温定着性に優れた電子写真用トナ−組成物

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0469752A1 (fr) * 1990-07-30 1992-02-05 MITSUI TOATSU CHEMICALS, Inc. Liant pour toner sec
US5241019A (en) * 1990-07-30 1993-08-31 Mitsui Toatsu Chemicals, Inc. Binder for dry toner
EP1480089A1 (fr) * 2002-02-28 2004-11-24 Sanyo Chemical Industries, Ltd. Liants de toner
EP1480089A4 (fr) * 2002-02-28 2005-09-14 Sanyo Chemical Ind Ltd Liants de toner
US7049041B2 (en) 2002-02-28 2006-05-23 Sanyo Chemical Industries, Ltd. Resin for toner binder and toner composition

Also Published As

Publication number Publication date
GB2237399A (en) 1991-05-01
GB9024263D0 (en) 1991-01-02

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