Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
• • 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
• • 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
  • C08G63/16—Dicarboxylic acids and dihydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
  • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy 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
  • G03G9/0819—Developers with toner particles characterised by the dimensions of the particles
• • 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
  • G03G9/0827—Developers with toner particles characterised by their shape, e.g. degree of sphericity
• • 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
• • 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
  • G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
  • G03G9/08795—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
• • 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
  • G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
  • G03G9/08797—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature

Definitions

• the present invention relates to a toner binder and a toner used for electrophotography, electrostatic recording, electrostatic printing, and the like.
• an electrophotographic toner binder for a heat fixing method adopted generally as a fixing method of an image in a copier, a printer, and the like that a toner does not fuse with a heat roll even at a high fixing temperature (hot offset resistance); that a toner can be fixed even at a low fixing temperature (low temperature fixing properties); that storage stability as fine particles is good (blocking resistance); and the like.
• toner binder composed of a polyester resin obtained by using a specific polyol component such as 1,2-propylene glycol and neopentyl glycol, without consideration for the SP value range and the HLB value range (Patent Document 2, etc.).
• the conventional toner composed of a matrix phase and a domain phase does not satisfy all of fixing properties (a balance between low temperature fixing properties and hot offset resistance) and storage stability sufficiently.
• fixing properties a balance between low temperature fixing properties and hot offset resistance
• storage stability sufficiently.
• An object of the present invention is to provide a toner binder having an increased range of fixing temperatures and excellent blocking resistance and charging characteristics when used as a toner; and a toner.
• the present invention includes the below-described two inventions.
• a toner binder containing a polyester resin (P) comprising one or more types of polyester resins obtained by polycondensation of a carboxylic acid component (x) and an alcohol component (y), wherein at least one type (P1) of (P) contains 50 to 95 mol % of an aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y), and (P) satisfies expressions (1) and (2).
• the use of the toner binder of the present invention makes it possible to provide a toner having an increased range of fixing temperatures and excellent blocking resistance and charging characteristics (saturated charge amount, charge rising properties, and charge stability).
• a toner binder of the present invention contains a polyester resin (P) comprising one or more types of polyester resins obtained by polycondensation of a carboxylic acid component (x) and an alcohol component (y).
• the polyester resin (P) may be one type of polyester resin, but preferably comprises a linear polyester resin (A) and a non-linear polyester resin (B). (A) and (B) may be each two or more types in combination.
• the polyester resin (P) it is necessary that at least one type (P1) of (P) contains 50 to 95 mol % of an aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y), from the viewpoint of fixing properties.
• the polyester resin (P) comprises a linear polyester resin (A) and a non-linear polyester resin (B)
• a linear polyester resin (A) corresponding to (P1) that contains 50 to 95 mol % of an aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y) may be described as a linear polyester resin (A•P1)
• a non-linear polyester resin (B) corresponding to (P1) that contains 50 to 95 mol % of an aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y) may be described as a non-linear polyester resin (B•P1).
• examples of the alcohol component (y) include a diol, a trivalent to octavalent or higher valent polyol, and a monool.
• diol examples include aliphatic diols (y1) having a carbon number of 2 to 4 (ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, diethylene glycol, etc.), aliphatic diols having a carbon number of 5 to 36 (neopentyl glycol, 2,3-dimethylbutane-1,4-diol, 1,6-hexanediol, 1,8-octanediol, etc.); alkylene ether glycols having a carbon number of 5 to 36 (triethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene ether glycol, etc.); alicyclic diols having a carbon number of 6 to 36 (1,4-cyclohexane dimethanol, hydrogenated bisphenol A, etc.); (poly)oxyalkylene (the carbon number of
• trivalent to octavalent or higher valent polyol examples include trivalent to octavalent or higher valent aliphatic polyalcohols having a carbon number of 3 to 36 (alkanepolyols and intramolecular or intermolecular dehydrates thereof, e.g. glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, sorbitol, sorbitan, polyglycerin, and dipentaerythritol; and saccharides and derivatives thereof, e.g.
• sucrose and methyl glucoside sucrose and methyl glucoside
• (poly)oxyalkylene ethers (the number of AO units is 1 to 30) of the above-described aliphatic polyalcohols; polyoxyalkylene ethers (the number of AO units is 2 to 30) of trisphenols (trisphenol PA, etc.); polyoxyalkylene ethers (the number of AO units is 2 to 30) of novolac resins (phenol novolac, cresol novolac, etc., the average polymerization degree is 3 to 60); and the like. Two or more types thereof may be used in combination.
• Preferred among these trivalent to octavalent or higher valent polyols are polyoxyalkylene ethers (the number of AO units is 2 to 30) of novolac resins.
• Examples of the monool include alkanols having a carbon number of 1 to 30 (methanol, ethanol, isopropanol, dodecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, etc.).
• alkanols having a carbon number of 8 to 24, and more preferred are dodecyl alcohol, myristyl alcohol, stearyl alcohol, and a combination thereof.
• examples of the alcohol component (y) include the aliphatic diol (y1) having a carbon number of 2 to 4, which is an essential constitutional component, as well as a diol (y2) of which the solubility parameter (hereinbelow, described as an SP value) is 11.5 to 16.0 [(cal/cm 3 ) 1/2 , the same applies hereinbelow], a trivalent to octavalent or higher valent polyol, a monool, and the like.
• SP values in the present invention are those calculated according to the method described in the below-described document suggested by Fedors et al. “POLYMER ENGINEERING AND SCIENCE, FEBRUARY, 1974, Vol. 14, No. 2, ROBERT F. FEDORS. (pages 147 to 154)”
• Examples of the aliphatic diol (y1) having a carbon number of 2 to 4 include the above-mentioned diols, and two or more types thereof may be used in combination.
• Preferred among these (y1) are ethylene glycol and 1,2-propylene glycol, and more preferred is ethylene glycol.
• Examples of the diol (y2) of which the SP value is 11.5 to 16.0 include, among the above-mentioned examples of diols, neopentyl glycol, 2,3-dimethylbutane-1,4-diol, cyclohexanedimethanol, polyoxyalkylene ethers of bisphenol A (the carbon number of the oxyalkylene group is 2 and/or 3, and the number of AO units is 2 to 30), polyoxyalkylene ethers of bisphenol F (the carbon number of the oxyalkylene group is 2 and/or 3, and the number of AO units is 2 to 30), polyoxyalkylene ethers of bisphenol S (the carbon number of the oxyalkylene group is 2 and/or 3, and the number of AO units is 2 to 30), hydrogenated bisphenol A, and the like. Two or more types thereof may be used in combination.
• neopentyl glycol and polyoxyalkylene ethers of bisphenol A Preferred among these are neopentyl glycol and polyoxyalkylene ethers of bisphenol A, and more preferred is neopentyl glycol.
• Examples of the trivalent to octavalent or higher valent polyol include the above-mentioned polyols, with the preferred ones being the same as well.
• the proportion of the aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y) is generally 50 to 95 mol %, preferably 60 to 93 mol %, from the viewpoint of fixing properties.
• the proportion of the diol (y2) of which the SP value is 11.5 to 16.0 in the alcohol component (y) is preferably 5 to 50 mol %, more preferably 7 to 40 mol %, from the viewpoint of storage stability.
• the carboxylic acid component (x) and/or the alcohol component (y) contain(s) at least one of a monool and a monocarboxylic acid (x1) mentioned later, and more preferable that the carboxylic acid component (x) contains a monocarboxylic acid (x1), from the viewpoint of storage stability and productivity.
• the monool is preferably used in such an amount (calculated value) that 5 mol % or more, more preferably 6 to 85 mol %, particularly preferably 8 to 80 mol %, most preferably 10 to 76 mol % of the terminal carboxyl groups of (A•P1) will be esterified with the monool, from the viewpoint of storage stability and productivity.
• the carboxylic acid component (x) comprises a polycarboxylic acid (x2), and if necessary a monocarboxylic acid (x1).
• the carboxylic acid component (x) comprises a monocarboxylic acid (x1) and a polycarboxylic acid (x2).
• examples of aliphatic (including alicyclic) monocarboxylic acids include alkane monocarboxylic acids having a carbon number of 1 to 30 (formic acid, acetic acid, propionic acid, butanoic acid, isobutanoic acid, caprylic acid, capric acid, lauric acid, myristyl acid, palmitic acid, stearic acid, behenic acid, cerotic acid, montanoic acid, melissic acid, etc.), and alkene monocarboxylic acids having a carbon number of 3 to 24 (acrylic acid, methacrylic acid, oleic acid, linoleic acid, etc.).
• aromatic monocarboxylic acids examples include aromatic monocarboxylic acids having a carbon number of 7 to 36 (benzoic acid, methylbenzoic acid, p-t-butylbenzoic acid, phenylpropionic acid, naphthoic acid, etc.).
• aromatic monocarboxylic acids having a carbon number of 7 to 36, and more preferred are benzoic acid, methylbenzoic acid, and p-t-butylbenzoic acid, and particularly preferred is benzoic acid.
• the monocarboxylic acid (x1) when a monocarboxylic acid (x1) is used, the monocarboxylic acid (x1) is preferably used in such an amount (calculated value) that 5 mol % or more, more preferably 6 to 85 mol %, particularly preferably 8 to 80 mol %, most preferably 10 to 76 mol % of the terminal hydroxyl groups of (A•P1) will be esterified with (x1), from the viewpoint of storage stability and productivity.
• the amount of the monocarboxylic acid (x1) is preferably 30 mol or less, more preferably 1 to 25 mol %, particularly preferably 2 to 21 mol % based on the total amount of the carboxylic acid component (x), from the viewpoint of storage stability.
• polycarboxylic acid (x2) examples include a dicarboxylic acid (x21) and/or a trivalent to hexavalent or higher valent polycarboxylic acid (x22).
• dicarboxylic acid (x21) examples include alkanedicarboxylic acids having a carbon number of 4 to 36 (e.g. succinic acid, adipic acid, and sebacic acid); alicyclic dicarboxylic acids having a carbon number of 6 to 40 [e.g. dimer acids (dimerized linoleic acids)]; alkenedicarboxylic acids having a carbon number of 4 to 36 (e.g.
• alkenyl succinic acids such as dodecenyl succinic acid, maleic acid, fumaric acid, citraconic acid, and mesaconic acid
• aromatic dicarboxylic acids having a carbon number of 8 to 36 (phthalic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, etc.); and ester-forming derivatives of these [lower alkyl (the carbon number of the alkyl group is 1 to 4: methyl, ethyl, n-propyl, etc.) esters, and acid anhydrides, the same applies to ester-forming derivatives hereinbelow], and two or more types thereof may be used in combination.
• alkenedicarboxylic acids having a carbon number of 4 to 20 aromatic dicarboxylic acids having a carbon number of 8 to 20, and ester-forming derivatives of these. More preferred are terephthalic acid, isophthalic acid and/or lower alkyl (the carbon number of the alkyl group: 1 to 4) esters (x211) of these.
• Examples of the trivalent to hexavalent or higher valent polycarboxylic acid (x22) include aromatic polycarboxylic acids having a carbon number of 9 to 20 (trimellitic acid, pyzomellitic acid, etc.), aliphatic polycarboxylic acids having a carbon number of 6 to 36 (hexanetricarboxylic acid, etc.), and ester-forming derivatives of these. Two or more types thereof may be used in combination.
• trimellitic acid trimellitic acid
• pyromellitic acid pyromellitic acid
• ester-forming derivatives of these Preferred among these are trimellitic acid, pyromellitic acid, and ester-forming derivatives of these.
• the content of terephthalic acid, isophthalic acid, and/or lower alkyl (the carbon number of the alkyl group: 1 to 4) esters (x211) of these in the polycarboxylic acid (x2) is preferably 85 to 100 mol %, more preferably 90 to 100 mol %, from the viewpoint of storage stability.
• the mole ratio of terephthalic acid and/or lower alkyl esters thereof to isophthalic acid and/or lower alkyl esters thereof in (x211) is preferably 20:80 to 100:0, more preferably 25:75 to 80:20, from the viewpoint of mechanical strength of the resin.
• the content of an aromatic carboxylic acid in the carboxylic acid component (x) is preferably 80 to 100 mol %, more preferably 85 to 100 mol %, from the viewpoint of storage stability and fixing properties.
• the proportion of the total amount of the trivalent to octavalent or higher valent polyol and the trivalent to hexavalent or higher valent polycarboxylic acid (x22) in the total amount of the carboxylic acid component (x) and the alcohol component (y) is preferably 0.1 to 15 mol %, more preferably 0.2 to 12 mol %. When it is 0.1 mol % or more, storage stability of the toner is good, and when it is 15 mol % or less, charging characteristics of the toner is good.
• a method of producing a linear polyester resin (A) by polycondensation of a carboxylic acid component (x) comprising a polycarboxylic acid (x2) and if necessary a monocarboxylic acid (x1), and an alcohol component (y) is not particularly limited.
• a mixture of (x1) and (x2) and (y) may undergo polycondensation at one operation.
• at least a part of (x2) and (y) may undergo polycondensation in advance in such an equivalence ratio that the hydroxyl groups of (y) are excessively present, then the hydroxyl groups of the obtained polycondensate (AO) are allowed to react with the carboxyl groups of (x1) for further polycondensation.
• a trivalent to hexavalent or higher valent polycarboxylic acid (x22) may be charged thereinto for further polycondensation, provided that practically one or two functional groups of the polycarboxylic acid (x22) are allowed to react, with the rest of functional groups being left unreacted.
• the reaction ratio of the alcohol component (y) to the carboxylic acid component (x) is, as an equivalence ratio of hydroxyl groups to carboxyl groups [OH]/[COOH], preferably 2/1 to 1/2, more preferably 1.5/1 to 1/1.3, particularly preferably 1.3/1 to 1/1.2.
• polycondensation of the carboxylic acid component (x) and the alcohol component (y) can be carried out by using a known esterification reaction.
• polycondensation can be carried out by allowing the esterification reaction to take place under an inert gas (nitrogen gas, etc.) atmosphere in the presence of a polymerization catalyst at a reaction temperature of preferably 150 to 280° C., more preferably 180 to 270° C., particularly preferably 200 to 260° C.
• the reaction time is preferably 30 minutes or more, particularly 2 to 40 hours, from the viewpoint of ensuring the polycondensation reaction.
• Pressure reduction is also effective in order to improve the reaction rate at the last stage of the reaction.
• the polyester synthesized by the above-described method may be subjected to a dehydration reaction in the presence of a strong acid such as sulfuric acid at 160 to 180° C. to produce terminal vinyl groups.
• a strong acid such as sulfuric acid at 160 to 180° C.
• the terminal vinyl groups are produced in the linear polyester resin (A•P1), they are preferably produced in such an amount (calculated value from the percentage of change in hydroxyl value: although two terminal hydroxyl groups may produce an ether bond as a by-product, the calculation is made provided that all are turned into vinyl groups) that 5 mol % or more, more preferably 6 to 85 mol %, particularly preferably 8 to 80 mol %, most preferably 10 to 76 mol % of the terminal hydroxyl groups of (A•P1) will be modified into vinyl groups, from the viewpoint of storage stability and productivity.
• a polymerization catalyst containing one or more types of metals selected from titanium, antimony, zirconium, nickel, and aluminum is preferably used, and a titanium-containing catalyst is more preferably used, from the viewpoint of reactivity and environmental protection.
• titanium-containing catalyst examples include titanium alkoxide, potassium oxalate titanate, titanium terephthalate, catalysts described in JP-A-2006-243715 [titanium dihydroxybis(triethanolaminate), titanium monohydroxytris(triethanolaminate), intramolecular polycondensates of these, etc.], catalysts described in JP-A-2007-11307 (titanium tributoxyterephthalate, titanium triisopropoxyterephthalate, titanium diisopropoxyditerephthalate, etc.), and the like.
• antimony-containing catalyst examples include antimony trioxide, and the like.
• zirconium-containing catalyst examples include zirconyl acetate, and the like.
• nickel-containing catalyst examples include nickel acetylacetonate, and the like.
• Examples of the aluminum-containing catalyst include aluminum hydroxide, aluminum triisopropoxide, and the like.
• the amount of catalyst to be added is appropriately decided such that the reaction rate reaches the maximum.
• the amount to be added is preferably 10 ppm to 1.9%, more preferably 100 ppm to 1.7%, based on the whole raw materials. When the amount to be added is 10 ppm or more, it is preferable in that the reaction rate is high.
• % refers to % by weight unless otherwise noted.
• the SP value of the linear polyester resin (A•P1) is preferably 11.3 to 13.0, more preferably 11.6 to 12.8.
• the SP value can be adjusted by the compositions and used amounts of raw materials: the carboxylic acid component (x) and the alcohol component (y).
• the acid value (AV) (mgKOH/g, the same applies hereinbelow) of the linear polyester resin (A) is preferably 0 to 60, more preferably 1 to 55, particularly preferably 2 to 50. When the acid value is 60 or less, charging characteristics in the case where the resin (A) is used in the toner are not deteriorated.
• the hydroxyl value (OHV) (mgKOH/g, the same applies hereinbelow) of the linear polyester resin (A) is preferably 0 to 125, more preferably 1 to 100. When the hydroxyl value is 125 or less, hot offset resistance and storage stability in the case where the resin (A) is used in the toner are better.
• the acid value and the hydroxyl value in the present invention are measured according to the method specified in JIS K0070.
• the peak top molecular weight (hereinbelow described as Mp) of a tetrahydrofuran soluble component of the linear polyester resin (A) is preferably 2000 to 12000, more preferably 2300 to 11500, particularly preferably 2500 to 11000.
• Mp is 2000 or more, the resin strength required for fixation is attained, and when it is 12000 or less, low temperature fixing properties in the case where the resin (A) is used in the toner are good.
• the peak top molecular weight (Mp) and the number average molecular weight (Mn) of the polyester resin are measured by using GPC under the conditions below.
• the molecular weight indicating the maximum peak height on the chromatogram obtained is referred to as a peak top molecular weight (Mp).
• Mp peak top molecular weight
• the softening point [Tm] of the linear polyester resin (A) is preferably 70 to 120° C., more preferably 75 to 110° C., particularly preferably 80 to 105° C. Within this range, the balance between hot offset resistance and low temperature fixing properties is good.
• Tm is a value measured as follows.
• the glass transition temperature [Tg] of the linear polyester resin (A) is preferably 45° C. or more, from the viewpoint of storage stability. When it is 75° C. or less, low temperature fixing properties in the case where the resin (A) is used in the toner are good.
• Tg is measured by using DSC20, SSC/580 manufactured by Seiko Instruments Inc. according to the method (DSC method) specified in ASTM D3418-82.
• a tetrahydrofuran (THF) insoluble component of the linear polyester resin (A) is preferably 5% or less, more preferably 4% or less, particularly preferably 3% or less, from the viewpoint of low temperature fixing properties in the case where the resin (A) is used in the toner.
• the THF insoluble component of the present invention is determined by the method below.
• THF (50 ml) is added to 0.5 g of a sample, and stirred at reflux for 3 hours. After cooling, an insoluble component is filtered out by a glass filter, and the resin component remaining on the glass filter is dried under reduced pressure at 80° C. for 3 hours. The insoluble component is calculated from the weight ratio of the dried resin component on the glass filter to the sample.
• the polyester resin (P) preferably contains a non-linear polyester resin (B) in addition to the linear polyester resin (A), from the viewpoint of achieving both low temperature fixing properties and offset resistance.
• examples of the alcohol component (y) include the above-mentioned diols, trivalent to octavalent or higher valent polyols, and monools.
• the non-linear polyester resin (B) is preferably a non-linear polyester resin (B•P1) that contains 50 to 95 mol % of an aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y) [in this section, the alcohol component (y) means an alcohol component to serve as a constitutional unit of the non-linear polyester resin (B), exclusive of the component removed to the outside of the system during a polycondensation reaction], from the viewpoint of fixing properties.
• the content of (y1) is more preferably 60 to 93 mol %.
• the proportion of the diol (y2) of which the SP value is 11.5 to 16.0 in the non-linear polyester resin (B•P1) is preferably 5 to 50 mol %, more preferably 7 to 40 mol %, from the viewpoint of storage stability.
• the carboxylic acid component (x) preferably comprises a monocarboxylic acid (x1) and a polycarboxylic acid (x2), from the viewpoint of charging characteristics.
• Examples of the monocarboxylic acid (x1) include the above-mentioned monocarboxylic acids, with the preferred ones being the same as well.
• the amount of the monocarboxylic acid (x1) is preferably 0.5 to 30 mol %, more preferably 1 to 25 mol %, particularly preferably 2 to 20 mol % based on the total amount of the carboxylic acid component (x), from the viewpoint of storage stability.
• Examples of the polycarboxylic acid (x2) include the above-mentioned polycarboxylic acids.
• dicarboxylic acids (x21) are alkenedicarboxylic acids having a carbon number of 4 to 20, aromatic dicarboxylic acids having a carbon number of 8 to 20, and ester-forming derivatives of these. More preferred are terephthalic acid, isophthalic acid, and/or lower alkyl (the carbon number of the alkyl group: 1 to 4) esters (x211) of these.
• Preferred among the trivalent to hexavalent or higher valent polycarboxylic acids (x22) are trimellitic acid, pyromellitic acid, and ester-forming derivatives of these.
• the content of terephthalic acid, isophthalic acid, and/or lower alkyl (the carbon number of the alkyl group: 1 to 4) esters (x211) of these in the polycarboxylic acid (x2) is preferably 85 to 100 mol %, more preferably 90 to 100 mol %, from the viewpoint of storage stability.
• the mole ratio of terephthalic acid and/or lower alkyl esters thereof to isophthalic acid and/or lower alkyl esters thereof in (x211) is preferably 20:80 to 100:0, more preferably 25:75 to 80:20, from the viewpoint of mechanical strength of the resin.
• the content of an aromatic carboxylic acid in the carboxylic acid component (x) is preferably 80 to 100 mol %, more preferably 85 to 100 mol %, from the viewpoint of storage stability and fixing properties.
• the content of an aromatic carboxylic acid in (x) is preferably within the above-described range.
• the carboxylic acid component (x) and/or the alcohol component (y) contain(s) at least one of a monool and a monocarboxylic acid (x1), and more preferable that the carboxylic acid component (x) contains a monocarboxylic acid (x1), from the viewpoint of storage stability and productivity.
• the monool is preferably used in such an amount (calculated value) that 5 mol % or more, more preferably 6 to 85 mol %, particularly preferably 8 to 80 mol %, most preferably 10 to 76 mol % of the terminal carboxyl groups of (B•P1) will be esterified with the monool, from the viewpoint of storage stability and productivity.
• the monocarboxylic acid (x1) is preferably used in such an amount (calculated value) that 5 mol % or more, more preferably 6 to 85 mol %, particularly preferably 8 to 80 mol %, most preferably 10 to 76 mol % of the terminal hydroxyl groups of (B•P1) will be esterified with (x1), from the viewpoint of storage stability and productivity.
• reaction conditions of polycondensation of the carboxylic acid component (x) and the alcohol component (y), and a polymerization catalyst to be used are the same as those described regarding the above-mentioned linear polyester resin (A).
• the reaction ratio of (y) to at least a part of (x2) is, as an equivalence ratio of hydroxyl groups to carboxyl groups (OH)/(COOH), preferably 2/1 to 1/1, more preferably 1.5/1 to 1.01/1, particularly preferably 1.3/1 to 1.02/1.
• the ratio of all the alcohol component (y) and all the carboxylic acid component (x) used in production of (B) is, as an equivalence ratio of hydroxyl groups to carboxyl groups [OH]/[COOH], preferably 2/1 to 1/2, more preferably 1.5/1 to 1/1.3, particularly preferably 1.3/1 to 1/1.2.
• the SP value of the non-linear polyester resin (B) is preferably 11.5 to 13.0, more preferably 11.8 to 12.8.
• the glass transition temperature [Tg] of the non-linear polyester resin (B) is preferably 45° C. to 75° C., more preferably 50° C. to 70° C. When Tg is 75° C. or less, low temperature fixing properties are improved. When Tg is 45° C. or more, blocking resistance is good.
• the softening point [Tm] of (B) is not particularly limited, but preferably 90° C. to 170° C., more preferably 120° C. to 160° C. When Tm is 90° C. or more, hot offset resistance is good. When Tm is 170° C. or less, fixing properties are good.
• Mp of a tetrahydrofuran (THF) soluble component of the non-linear polyester resin (B) is preferably 3000 to 30000, more preferably 3200 to 25000, particularly preferably 3500 to 12000.
• a THF insoluble component of the non-linear polyester resin (B) is preferably 3 to 50%, from the viewpoint of low temperature fixing properties. It is more preferably 5 to 40%, particularly preferably 10 to 35%. When the THF insoluble component is 50% or less, the glossiness (gloss) of images is good.
• the acid value (AV) of the non-linear polyester resin (B) is preferably 0 to 40, more preferably 3 to 30, and the hydroxyl value (OHV) thereof is preferably 0 to 30, more preferably 0 to 20.
• the sum of the acid value and the hydroxyl value of the non-linear polyester resin (B) is preferably 3 to 40, more preferably 10 to 40, particularly preferably 20 to 39.
• the sum of the acid value and the hydroxyl value is 3 or more, storage stability is good, and when it is 40 or less, charge stability is improved.
• the weight ratio of (A) to (B) [(A)/(B)] is preferably 15/85 to 90/1.0, more preferably 20/80 to 80/20, from the viewpoint of achieving both low temperature fixing properties and hot offset resistance/pulverization properties.
• the SP value of the polyester resin (P) [this preferably comprises the linear polyester resin (A) and the non-linear polyester resin (B)] contained in the toner binder of the present invention needs to satisfy the below-described expression (1), from the viewpoint of fixing properties and storage stability, and it is preferably 11.6 to 12.9.
• the above-described SP value is, when (P) comprises two or more kinds of polyester resins, a value determined by a weighted average of SP values of each resin.
• the HLB value of the polyester resin (P) needs to satisfy the below-described expression (2), from the viewpoint of fixing properties and storage stability, and it is preferably 5.5 to 7.0.
• the above-described HLB value is, when (P) comprises two or more kinds of polyester resins, a value determined by a weighted average of HLB values of each resin.
• the HLB Heydrophile-Lipophile Balance
• Oda Oda method according to the below-described expression.
• the HLB value can be adjusted by the compositions and used amounts of raw materials of (P): the carboxylic acid component (x) and the alcohol component (y).
• a polyester resin (P1) containing 50 to 95 mol % of an aliphatic diol (y1) having a carbon number of 2 to 4 in the alcohol component (y) contained in the polyester resin (P) has, in most cases, an HLB value of more than 7.1, mentioned are the methods (1) and (2), which are employed in at least one of the linear polyester resin (A•P1) and the non-linear polyester resin (B•P1) or preferably in both of them:
• Specific examples of (2) include, as the above-mentioned methods, a method of esterifying 5 mol % or more of the terminal hydroxyl groups with a monocarboxylic acid, a method of esterifying 5 mol % or more of the terminal carboxyl groups with a monool, and a method of modifying 5 mol % or more of the terminal hydroxyl groups into vinyl groups.
• the method of (2) is a method of performing esterification with a monocarboxylic acid or a monool to block the terminal functional group. Particularly preferred is a method of performing esterification with a monocarboxylic acid.
• polyester resin (P) preferably satisfies the following expression (3). When this expression is satisfied, storage stability and fixing properties are better.
• (P) comprises two or more types of polyester resins
• Mn and Tg of the whole (P) as a mixture of these, and the SP value (weighted average value) are used.
• linear polyester resin (A) and the non-linear polyester resin (B) constituting (P) preferably satisfy the expression (3).
• Examples of a method of obtaining the polyester resin (P) satisfying the expression (3) include a method of increasing the content percentage of an aliphatic diol (y1) having a carbon number of 2 to 4 to increase the SP value, a method of increasing the content percentage of a monocarboxylic acid (x1) to increase Tg relative to Mn, and the like.
• the toner binder of the present invention may contain resins other than the polyester resin (P) as long as the effect of the present invention is not impaired.
• resins include vinyl resins [copolymers of styrene and alkyl (meth)acrylate, copolymers of styrene and diene monomer, etc.], epoxy resins (ring-opening polymers of bisphenol A diglycidylether, etc.), urethane resins (polyadducts of the above-mentioned alcohol component and diisocyanate, etc.), and the like.
• the Mp of such other resins is preferably 300 to 100000.
• the mixing properties of (A) with (B) in the case where the polyester resin (P) comprises the linear polyester resin (A) and the non-linear polyester resin (B) can be evaluated by observation at 100 or more magnifications (preferably 100 to 5000 magnifications) of a phase-contrast microscope and a digital microscope (high-resolution optical microscope).
• the toner particle diameter is generally about 5 to 10 ⁇ m, and therefore in the case where (A) and (B) forms a sea-island structure, the dispersion particle diameter of the island phase being 5 ⁇ m or less is determined as good mixing properties.
• the dispersion particle diameter is more preferably 4 ⁇ m or less, particularly preferably 0.1 to 3 ⁇ m. When the dispersion particle diameter is 5 ⁇ m or less, low temperature fixing properties and hot offset resistance are good.
• mixing properties is performed by the measurement using an IX71 phase-contrast microscope (research inverted microscope) manufactured by OLYMPUS CORPORATION and/or a digital microscope (high-resolution zoom lens VH-Z500R/Z500W) manufactured by KEYENCE CORPORATION.
• a toner of the present invention can be made by adding a colorant, and if necessary one or more types of additives such as a release agent, a charge control agent, a magnetic powder, and a fluidizing agent to the toner binder of the present invention.
• any dyes, pigments and the like used as colorants for toner can be used.
• Specific examples thereof include carbon black, iron black, sudan black SM, fast yellow G, benzidine yellow, pigment yellow, indofast orange, Irgazin red, paranitroaniline red, toluidine red, carmine FB, pigment orange R, lake red 2G, rhodamine FB, rhodamine B lake, methyl violet B lake, phthalocyanine blue, pigment blue, brilliant green, phthalocyanine green, oil yellow GG, Kayaset YG, orasol brown B and oil pink OP. These may be used singly or two or more of them may be mixed and used.
• a magnetic powder (a powder of ferromagnetic metals such as iron, cobalt, and nickel or compounds such as magnetite, hematite, and ferrite) may be contained to serve also as a colorant.
• those having a softening point [Tm] of 50 to 170° C. are preferable, and examples thereof include polyolefin wax, natural wax, aliphatic alcohols having a carbon number of 30 to 50, fatty acids having a carbon number of 30 to 50, and mixtures of these.
• the polyolefin wax include: (co)polymers of olefins (e.g.
• maleic anhydride monomethyl maleate, monobutyl maleate, dimethyl maleate, etc.
• copolymers of olefins and unsaturated carboxylic acids [(meth)acrylic acid, itaconic acid, maleic anhydride, etc.] and/or unsaturated carboxylic acid alkyl esters [(meth)acrylic acid alkyl (the carbon number of alkyl is 1 to 18) esters, maleic acid alkyl (the carbon number of alkyl is 1 to 18) esters, etc.] and the like, sasol wax, and the like.
• Examples of the natural wax include carnauba wax, montan wax, paraffin wax and rice wax.
• Examples of the aliphatic alcohols having a carbon number of 30 to 50 include triacontanol.
• Examples of the fatty acids having a carbon number of 30 to 50 include triacontan carboxylic acid.
• Examples of the charge control agent include nigrosine dyes, triphertylmethane-based dyes containing a tertiary amine as a side chain, quaternary ammonium salts, polyamine resins, imidazole derivatives, quaternary ammonium base-containing polymers, metal-containing azo dyes, copper phthalocyanine dyes, metal salts of salicylic acid, boron complexes of benzilic acid, sulfonic acid group-containing polymers, fluorine-containing polymers, halogen-substituted aromatic ring-containing polymers, and the like.
• Examples of the fluidizing agent include colloidal silica, alumina powder, titanium oxide powder, calcium carbonate powder, and the like.
• the toner binder of the present invention accounts for preferably 30 to 97%, more preferably 40 to 95%, particularly preferably 45 to 92%; the colorant accounts for preferably 0.05 to 60%, more preferably 0.1 to 55%, particularly preferably 0.5 to 50%; among additives, the release agent accounts for preferably 0 to 30%, more preferably 0.5 to 20%, particularly preferably 1 to 10%; the charge control agent accounts for preferably 0 to 20%, more preferably 0.1 to 10%, particularly preferably 0.5 to 7.5%; and the fluidizing agent accounts for preferably 0 to 10%, more preferably 0 to 5%, particularly preferably 0.1 to 4%.
• the total content of the additives is preferably 3 to 70%, more preferably 4 to 58%, particularly preferably 5 to 50%.
• the toner may be obtained by any of conventionally known methods such as a kneading-pulverization method, an emulsion phase-inversion method, and a polymerization method.
• the toner in obtaining a toner by a kneading-pulverization method, can be produced by dry-blending the components other than a fluidizing agent which are to constitute the toner, melt-kneading and then coarsely pulverizing the blend, finally finely pulverizing the blend using a jet mill pulverizer or the like, further classifying the resultant to form fine particles preferably having a particle diameter (D50) of 5 to 20 ⁇ m, and then mixing a fluidizing agent.
• D50 particle diameter
• the average particle diameter (D50) (in the volume particle diameter distribution of a powder, when the number of particles having a particle diameter greater than a certain particle diameter accounts for 50% of the number of particles of whole powder, such a certain particle diameter is determined as D50) is measured using a Coulter counter [e.g. commercial name: Multisizer III (manufactured by Beckman Coulter, Inc.)].
• the toner can be produced by dissolving or dispersing the components other than a fluidizing agent which are to constitute the toner in an organic solvent, emulsifying them, for example, by addition of water, and then conducting separation and classification.
• the volume average particle diameter of the toner is preferably 3 to 15 ⁇ m.
• the toner of the present invention using the toner binder of the present invention is mixed with carrier particles such as iron powder, glass beads, nickel powder, ferrite, magnetite, or ferrite the surface of which is coated with a resin (acrylic resin, silicone resin, etc.), if necessary, to be used as a developer of an electric latent image.
• carrier particles such as iron powder, glass beads, nickel powder, ferrite, magnetite, or ferrite the surface of which is coated with a resin (acrylic resin, silicone resin, etc.), if necessary, to be used as a developer of an electric latent image.
• the weight ratio of the toner to the carrier particles is preferably 1/99 to 100/0. It is also possible to form an electric latent image by friction with a member such as a charging blade instead of carrier particles.
• the toner of the present invention is fixed on a support (paper, a polyester film, etc.) by a copier, a printer or the like to be formed into a recorded material.
• a support paper, a polyester film, etc.
• fixing methods on a support known heat roll fixing methods, flash fixing methods, and the like can be applied. Fixing methods, flash fixing methods, and the like can be applied.
• part(s) represents “part(s) by weight”.
• the (A-1) had an Mp of 3500, an Mn of 1600, a Tg of 58° C., a Tm of 95° C., an acid value of 15, a hydroxyl value of 65, a THF insoluble component of 1%, an SP value of 11.3 and an HLB value of 4.8.
• mol % in the parentheses represents mol % of each raw material contained in the carboxylic acid component or the alcohol component. The same shall apply hereinafter.
• a reaction vessel equipped with a condenser, a stirrer and a nitrogen inlet tube Into a reaction vessel equipped with a condenser, a stirrer and a nitrogen inlet tube were charged 290 parts (90.3 mol %) of terephthalic acid, 735 parts (100.0 mol %) of a ethylene oxide (hereinafter abbreviated as EO) adduct of bisphenol A: highly purified BPE-20 (SP value: 12.5) (Manufactured by Sanyo Chemical Industries, Ltd.: purity of the 2 moles of EO adduct being 98), and 3 parts of titanium diisopropoxy bis(triethanol aminate) serving as a polymerization catalyst, and these were allowed to react at 210° C. under a nitrogen gas flow for 5 hours while generated water being distilled off.
• EO ethylene oxide
• the (A-3) had an Mp of 5000, an Mn of 2100, a Tg of 60° C., a Tm of 97° C., an acid value of 25, a hydroxyl value of 21, a THF insoluble component of 1%, an SP value of 12.1, an HLB value of 6.5 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 29 mol %.
• the (A-4) had an Mp of 5700, an Mn of 2350, a Tg of 59° C., a Tm of 102° C., an acid value of 20, a hydroxyl value of 12, a THF insoluble component of 1%, an SP value of 12.3, an HLB value of 7.0 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 40 mol %.
• the (A-6) had an Mp of 4000, an Mn of 1700, a Tg of 58° C., a Tm of 93° C., an acid value of 11, a hydroxyl value of 10, a THF insoluble component of 1%, an SP value of 12.0, an HLB value of 5.8 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 74 mol %.
• the (A-7) had an Mp of 4400, an Mn of 1800, a Tg of 61° C., a Tm of 95° C., an acid value of 15, a hydroxyl value of 17, a THF insoluble component of 1%, an SP value of 12.4, an HLB value of 6.8 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 55 mol %.
• the (A-8) had an Mp of 4800, an Mn of 2000, a Tg of 60° C., a Tm of 98° C., an acid value of 20, a hydroxyl value of 26, a THF insoluble component of 1%, an SP value of 12.3, an HLB value of 6.5 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 29 mol %.
• the (A-9) had an Mp of 5400, an Mn of 2250, a Tg of 57° C., a Tm of 101° C., an acid value of 25, a hydroxyl value of 6, a THF insoluble component of 1%, an SP value of 12.4, an HLB value of 6.9 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 59 mol %.
• the (A-10) had an Mp of 6000, an Mn of 2400, a Tg of 62° C., a Tm of 104° C., an acid value of 20, a hydroxyl value of 1, a THF insoluble component of 1%, an SP value of 12.1, an HLB value of 6.7 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 72 mol %.
• the (A-11) had an Mp of 4100, an Mn of 1700, a Tg of 63° C., a Tm of 97° C., an acid value of 15, a hydroxyl value of 12, a THF insoluble component of 1%, an SP value of 11.8, an HLB value of 6.6 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 67 mol %.
• the (A-12) had an Mp of 6000, an Mn of 2200, a Tg of 59° C., a Tm of 102° C., an acid value of 25, a hydroxyl value of 13, a THF insoluble component of 1%, an SP value of 11.8, an HLB value of 6.1 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 37 mol %.
• the (A-13) had an Mp of 8000, an Mn of 3000, a Tg of 61° C., a Tm of 109° C., an acid value of 25, a hydroxyl value of 17, a THF insoluble component of 1%, an SP value of 11.8, an HLB value of 6.2 and an esterification rate of terminal carboxylic group by monool of 33 mol %.
• the (A-14) had an Mp of 5900, an Mn of 2400, a Tg of 59° C., a Tm of 103° C., an acid value of 25, a hydroxyl value of 10, a THF insoluble component of 2%, an SP value of 12.2, an HLB value of 7.0 and a modification rate of terminal hydroxyl group to vinyl group of 75 mol %.
• the (B-1) had an Mp of 8000, an Mn of 2200, a Tg of 60° C., a Tm of 145° C., an acid value of 26, a hydroxyl value of 1, a THF insoluble component of 4%, an SP value of 11.8, an HLB value of 6.9 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 19 mol %.
• the (B-2) had an Mp of 4500, an Mn of 1500, a Tg of 63° C., a Tm of 150° C., an acid value of 23, a hydroxyl value of 5, a THF insoluble component of 8%, an SP value of 12.0, an HLB value of 6.8 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 60 mol %.
• the (B-3) had an Mp of 5200, an Mn of 1900, a Tg of 61° C., a Tm of 148° C., an acid value of 24, a hydroxyl value of 5, a THF insoluble component of 6%, an SP value of 12.0, an HLB value of 6.8 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 51 mol %.
• the (B-4) had an Mp of 4600, an Mn of 1600, a Tg of 62° C., a Tm of 151° C., an acid value of 16, a hydroxyl value of 7, a THF insoluble component of 6%, an SP value of 11.9, an HLB value of 6.9 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 64 mol %.
• the (B-5) had an Mp of 4800, an Mn of 1700, a Tg of 63° C., a Tm of 155° C., an acid value of 20, a hydroxyl value of 0.1, a THF insoluble component of 20%, an SP value of 12.0, an HLB value of 6.2 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 76 mol %.
• the (RA-1) had an Mp of 6100, an Mn of 2500, a Tg of 59° C., a Tm of 103° C., an acid value of 20, a hydroxyl value of 29, a THF insoluble component of 1%, an SP value of 12.5 and an HLB value of 7.5.
• the (RA-2) had an Mp of 6000, an Mn of 2600, a Tg of 62° C., a Tm of 94° C., an acid value of 10, a hydroxyl value of 14, a THF insoluble component of 1%, an SP value of 11.0, an HLB value of 4.1 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 54 mol %.
• the (RB-1) had an Mp of 8500, an Mn of 2600, a Tg of 57° C., a Tm of 140° C., an acid value of 30, a hydroxyl value of 5, a THF insoluble component of 5%, an SP value of 12.6, an HLB value of 7.5 and an esterification rate of terminal hydroxyl group by monocarboxylic acid of 21 mol %.
• the (RB-2) had an Mp of 8500, an Mn of 2400, a Tg of 58° C., a Tm of 145° C., an acid value of 24, a hydroxyl value of 3, a THF insoluble component of 4%, an SP value of 11.7 and an HLB value of 6.7.
• the linear polyester resins (A), the non-linear polyester resins (B), the comparative linear polyester resins (RA), and the comparative non-linear polyester resins (RB) obtained in Production Examples 1 to 19 and Comparative Production Examples 1 to 4 were each charged into a plastomill at the ratio shown in Table 2, and stirred at 140° C. for 10 minutes for melt-mixing, so that toner binders (TB-1) to (TB-23) of the present invention composed of the polyester resin (P) and comparative toner binders (TB′-1) to (TB′-4) were obtained. Based on 100 parts of each toner binder, 8 parts of cyanine blue KRO (manufactured by Sanyo Color Works, Ltd.) and 5 parts of carnauba wax were added. The obtained mixture was made into a toner by the below-described method.
• the obtained mixture was premixed using a Henschel mixer [FM10B manufactured by Mitsui Miike Kakoki KK.] and kneaded in a twin-screw kneader [PCM-30 manufactured by Ikegai Corp.].
• the mixture was then finely pulverized using a supersonic jet pulverizer Labojet [manufactured by Nippon Pneumatic Mfg. Co., Ltd.], followed by classification using an air classifier [MDS-I manufactured by Nippon Pneumatic Mfg. Co., Ltd.] to obtain toner particles having a volume average particle diameter (D50) of 8 ⁇ m.
• colloidal silica (Aerosil R972: manufactured by Nippon Aerosil Co., Ltd.) was mixed with 100 parts of the toner particles in a sample mill to obtain toners (T-1) to (T-23) of the present invention and comparative toners (T′-1) to (T′-4).
• An unfixed image developed by a commercially available copier (AR5030; manufactured by SHARP CORPORATION) was evaluated by using a fixing device of the commercially available copier (AR5030; manufactured by SHARP CORPORATION).
• the fixing roll temperature at which the remaining percentage of the image density after the fixed image was rubbed with a pad became 70% or more was defined as a minimum fixing temperature.
• the fixing roll temperature at which hot offset occurred was defined as a hot offset occurrence temperature.
• MFT minimum fixing temperature
• HAT hot offset occurrence temperature
• Each of the toners was charged into a polyethylene bottle and kept in a constant temperature water tank at 45° C. for 8 hours. Then, it was transferred onto a 42-mesh sieve and vibrated with a powder tester manufactured by Hosokawa Micron Corporation at a vibration intensity of 5 for 10 seconds. The weight % of the toner remaining on the sieve was measured and determined in accordance with the below-described criteria to evaluate storage stability. Weight % of remaining toner
• ⁇ 0% or more and less than 15% ⁇ : 15% or more and less than 25% ⁇ : 25% or more and less than 30% x: More than 30%
• the absolute value of the saturated charge amount is 25 ⁇ C/g or more ⁇ : The absolute value of the saturated charge amount is 20 ⁇ C/g or more and less than 25 ⁇ C/g ⁇ : The absolute value of the saturated charge amount is 15 ⁇ C/g or more and less than 20 ⁇ C/g x: The absolute value of the saturated charge amount is less than 15 ⁇ C/g
• ⁇ 0.7 or more ⁇ : 0.6 or more and less than 0.7 ⁇ : 0.5 or more and less than 0.6 x: less than 0.5
• the toners of the present invention (Examples 1 to 23) using the toner binder of the present invention all provided significantly good results on, in particular, charging characteristics and blocking resistance, as compared with the comparative toners (Comparative Examples 1 to 4) using the comparative toner binder.
• the toner of the present invention using the toner binder of the present invention is excellent in the range of fixing temperatures, storage stability, and the like, so that it is useful as a toner used for electrophotography, electrostatic recording, electrostatic printing, and the like.

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• 2011
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