Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents 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
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/091—Azo dyes
• • 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
  • G03G9/0802—Preparation methods
  • G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
• • 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
  • G03G9/0802—Preparation methods
  • G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
  • G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
• • 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
  • G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • G03G9/08706—Polymers of alkenyl-aromatic compounds
  • G03G9/08708—Copolymers of styrene
• • 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
• • 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
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/0912—Indigoid; Diaryl and Triaryl methane; Oxyketone dyes

Definitions

• the present invention relates to a yellow toner to be used for a recording method, such as an
• electrophotography method an electrostatic recording method, a magnetic recording method, and a toner jet method, and to a process for producing the yellow toner .
• the image quality is strongly influenced by coloring power of colorants in the respective color developers .
• C. I. pigment yellow 185 can hardly be dispersed sufficiently as a colorant in a binder resin, because of self-aggregation tendency due to the innate nature of the pigment.
• the pigment has good weather resistance, a technology, which can exert fully the intrinsic performance of the pigment, has not yet been established in terms of clarity or saturation.
• the present invention provides a yellow toner comprising toner particles which contain at least a binder resin, a wax, and a colorant, wherein the colorant comprises C. I. pigment yellow 185 and a compound represented by the general formula (1), and a process for producing the same.
• A represents -S0 2 N(R 4 )R5 or -CON(R 4 )R 5
• R 4 represents a hydrogen atom or an alkyl group
• R 5 represents an alkyl group
• Ri represents an alkyl group, an aryl group, or an amino group
• R3 represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group
• R 2 represents
• a yellow toner which is superior in dispersibility of the C. I. pigment yellow 185, has a high color development property, and also is superior in light resistance, can be provided.
• Fig. 1 is a diagram illustrating a " " " H NMR spectrum at 400 MHz in DMSO-d 6 at room temperature, of the
• A represents -S0 2 N(R 4 )R 5 or -CON(R 4 )R 5
• R 4 represents a hydrogen atom or an alkyl group
• R 5 represents an alkyl group
• Ri represents an alkyl group, an aryl group, or an amino group
• R 3 represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group
• R 2 represents
• branched alkyl group a CI to C12 straight-chain, or branched alkyl group is preferable, a CI to CIO straight-chain, or branched alkyl group is more preferable, and a methyl group is further preferable.
• a monocyclic or a polycyclic aryl group with a 6 to 14-membered ring such as a phenyl group and a naphthyl group.
• a phenyl group is preferable.
• a carboxylate ester group for R 2 in the general formula (1) there is no particular restriction on a carboxylate ester group for R 2 in the general formula (1), and examples thereof include a methyl carboxylate ester group, an ethyl carboxylate ester group, a propyl carboxylate ester group, and a butyl carboxylate ester group .
• a carboxylic acid amide group for R 2 in the general formula (1) there is no particular restriction on a carboxylic acid amide group for R 2 in the general formula (1), and examples thereof include a mono-substituted amide group, such as a carbamoyl group, a carboxylic acid methylamide group, a carboxylic acid butylamide group, a carboxylic acid hexylamide group, and a carboxylic acid phenylamide group; and a di-substituted amide group, such as a carboxylic acid dimethylamide group, a carboxylic acid diphenylamide group, and a
• cyano group for R 2 because of good dispersibility of C. I. pigment yellow 185.
• R3 represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group. Among others, R3 is preferably a hydrogen atom or an alkyl group.
• R 3 when R 3 is a hydrogen atom, R 2 represents a hydrogen atom, a cyano group, or a carbamoyl group, and (ii) when R 3 is an alkyl group, an aryl group, or an aralkyl group, R 2 represents a hydrogen atom, a cyano group, a carboxylic acid group, a carboxylate ester group, a carboxylic acid amide group, or a carbamoyl group.
• branched alkyl group Among others, a Cl to C12 straight-chain, or branched alkyl group is preferable.
• a monocyclic or a polycyclic aryl group with a 6 to 14-membered ring such as a phenyl group and a naphthyl group.
• a phenyl group is preferable.
• R 2 is a cyano group or a carboxylic acid amide group and R 3 is a C2 to C12 alkyl group, because of good dispersibility of C. I. pigment yellow 185.
• A represents -S0 2 N(R 4 )R 5 or -CON(R 4 )R5
• R 4 represents a hydrogen atom or an alkyl group
• R 5 represents an alkyl group.
• -CON(R 4 )R 5 is preferable, and more preferably R 4 and R5 have the same structure.
• branched alkyl group a C4 to C12 straight-chain, or branched alkyl group is preferable, a C6 to CIO straight-chain, or branched alkyl group is more preferable, and a branched
• ethylhexyl group is further preferable.
• A is preferably -CON (R 4 ) R 5 .
• compounds (5), (8), (10), (11), (15), (16), (21), (22), (23), (24), (25), and (26) are preferable, and compounds (8), (10), (11), (23), (24), (25), and (26) are more preferable.
• a compound represented by the general formula (1) to be used in the present invention may be used singly or in combination with one or more known yellow dyes, depending on a production unit for each toner, and for adjusting the color tone, etc.
• binder resin there is no particular restriction on a binder resin to be used in the present invention and examples thereof include a thermoplastic resin.
• styrenes such as styrene, p- chlorostyrene, and -methylstyrene
• a homopolymer or a copolymer of esters having a vinyl group such as methyl acrylate, ethyl acrylate, n- propyl acrylate, n-butyl acrylate, lauryl acrylate, 2- ethylhexyl acrylate, methyl methacrylate , ethyl
• a vinyl resin such as acrylonitrile and methacrylonitrile
• a homopolymer or a copolymer of vinyl ethers (a vinyl resin) , such as vinyl ethyl ether and vinyl isobutyl ether
• a homopolymer or a copolymer of olefins (an olefinic resin) such as ethylene, propylene, butadiene, and isoprene
• a non-vinyl condensation resin such as an epoxy resin, a polyester resin, a polyurethane resin, a polyamide resin, a cellulosic resin, and a polyether resin
• a graft polymer of the non-vinyl condensation resin with a vinyl nitriles such as acrylonitrile and methacrylonitrile
• a polyester resin is synthesized from an acid-derived component (dicarboxylic acid) and an alcohol-derived component (diol) , while for the purpose of the present invention, "an acid-derived component” refers to a moiety, which was an acid component before the
• an alcohol- derived component refers to a moiety, which was an alcohol component before the synthesis of a polyester resin.
• an acid-derived component there is no particular restriction on an acid-derived component according to the present invention, and examples thereof include an aliphatic dicarboxylic acid-derived component, a dicarboxylic acid-derived component with a double bond, and a dicarboxylic acid- derived component with a sulfonic acid group.
• oxalic acid examples thereof include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1 , 9-nonanedicarboxylic acid, 1 , 10-decanedicarboxylic acid, 1, 11-undecanedicarboxylic acid, 1,12- dodecanedicarboxylic acid, 1 , 13-tridecanedicarboxylic acid, 1, 14-tetradecanedicarboxylic acid, 1,16- hexadecanedicarboxylic acid, 1,18- octadecanedicarboxylic acid, and a lower alkyl ester or an acid anhydride thereof.
• an acid examples thereof include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid
• aliphatic dicarboxylic acid-derived component is desirable, and it is further preferable if the
• aliphatic moiety of an aliphatic dicarboxylic acid is a saturated carboxylic acid.
• an alcohol- derived component there is no particular restriction on an alcohol- derived component, but an aliphatic diol is desirable.
• examples include ethylene glycol, 1, 3-propanediol, 1, -butanediol, 1 , 5-pentanediol , 1 , 6-hexanediol , 1,7- heptanediol, 1 , 8-octanediol , 1 , 9-nonanediol , 1,10- decanediol, 1 , 11-dodecanediol , 1 , 12-undecanediol , 1 , 13-tridecanediol , 1, 14-tetradecanediol, 1,18- octadecanediol , and 1, 20-eicosanediol .
• a crosslinking agent may be used when a binder resin is synthesized in order to increase the mechanical strength of a toner particle and to regulate the molecular weight of a toner molecule .
• a crosslinking agent to be used for a toner according to the present invention
• examples of a bifunctional crosslinking agent include divinyl benzene, bis (4- acryloxypolyethoxyphenyl ) propane, ethylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4- butanediol diacrylate, 1 , 5-pentanediol diacrylate, 1 , 6-hexanediol diacrylate, neopentylglycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate,
• polypropylene glycol diacrylate polyester-type diacrylate, ethylene glycol dimethacrylate, 1,3- butylene glycol dimethacrylate, 1 , -butanediol
• dimethacrylate 1 , 5-pentanediol dimethacrylate, 1,6- hexanediol dimethacrylate, neopentylglycol
• dimethacrylate diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, respective dimethacrylates of polyethylene glycol #200, #400, and #600, dipropylene glycol dimethacrylate, polypropylene glycol
• dimethacrylate and polyester-type dimethacrylate.
• polyfunctional crosslinking agent examples thereof include pentaerythritol triacrylate, trimethylolethane
• tetramethylolmethane tetraacrylate an oligoester acrylate and a methacrylate thereof, 2,2-bis(4- methacryloxyphenyl ) propane, diallyl phthalate,
• the crosslinking agent is used preferably in an amount of 0.05 to 10 parts by mass, more preferably 0.1 to 5 parts by mass with respect to 100 parts by mass of the monomer.
• invention includes a grinding process, a suspension polymerization process, a suspension granulation process, an emulsion polymerization process, and an emulsion aggregation process.
• a grinding process a suspension polymerization process, a suspension granulation process, an emulsion polymerization process, and an emulsion aggregation process.
• a suspension polymerization process and an emulsion aggregation process are preferable, and a suspension polymerization process and an emulsion aggregation process are more
• a production process in which particles are formed in an aqueous medium is preferable.
• the toner of the present invention is also used in a developer used in a liquid development process
• liquid developer (hereinafter referred to as "a liquid developer").
• a step for dispersing a pigment to produce a pigment dispersion product (also called as "a masterbatch” ) is required.
• the pigment dispersion product can be obtained by a
• C. I. pigment yellow 185 and the compound represented by the general formula (1) according to the present invention can be dispersed by a known dispersing process.
• the dispersion can be conducted for example as follows.
• C. I. pigment yellow 185 and a compound represented by the general formula (1), as well as, according to need, a resin are dissolved in a
• pigments can be finely dispersed as stable homogeneous fine particles.
• C. I. pigment yellow 185 is suspended therein, and a compound represented by the general formula (1) is added gradually with stirring to mix up thoroughly with the dispersion medium. Then a
• a disperser used in the present invention there is no particular restriction on a disperser used in the present invention, and preferable examples include a media-type disperser, such as a rotational shear homogenizer, a ball mill, a sand mill, and
• Attritor and a high pressure collision type disperser.
• dispersion product according to the present invention is 1.0 to 30.0 parts by mass, preferably 2.0 to 20.0 parts by mass, and more preferably 3.0 to 15.0 parts by mass with respect to 100 parts by mass of a
• dispersion medium within the range, good coloring power can be attained.
• a compound represented by the general formula (1) is used preferably in an amount of 10 to 100 parts by mass, especially 15 to 80 parts by mass with respect to 100 parts by mass of C. I. pigment yellow 185.
• the pigment dispersion product may be dispersed in
• a disperser used in the present invention is no particular restriction on a disperser used in the present invention, and preferable examples include a media-type disperser, such as a rotational shear homogenizer, a ball mill, a sand mill, and
• Attritor and a high pressure collision type disperser.
• a polymerizable monomer is preferably used.
• a polymerizable monomer is a monomer polymerizable by addition or polymerizable by condensation, and
• preferably is a monomer polymerizable by addition.
• styrenic monomer such as styrene, o-methylstyrene, m-methylstyrene, p- methylstyrene , o-ethylstyrene , m-ethylstyrene , and p- ethylstyrene; an acrylate monomer, such as methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, octyl acrylate, dodecyl acrylate, stearyl acrylate, behenyl acrylate, 2-ethylhexyl acrylate, dimethylaminoethyl acrylate, diethylaminoethyl
• styrenic monomer such as styrene, o-methylstyrene, m-methylstyrene, p- methylstyrene , o
• acrylate acrylonitrile, and acrylic acid amide
• methacrylate monomer such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl
• methacrylonitrile and methacrylic acid amide
• an olefinic monomer such as ethylene, propylene,
• halogenated vinyls such as vinyl
• vinylidene chloride vinyl bromide, and vinyl iodide
• vinyl esters such as vinyl acetate, vinyl propionate, and vinyl benzoate
• vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl isobutyl ether
• a vinyl ketone compound such as vinyl methyl ketone, vinyl hexyl ketone, and methyl isopropenyl ketone.
• these may be used singly or in combinations of two or more thereof.
• product according to the present invention is used for a polymerized toner application, among the above- listed polymerizable monomers, preferably styrene or a styrenic monomer is used singly or in a mixture with another polymerizable monomer. From a standpoint of easy handling, styrene is preferable.
• a resin usable for a pigment dispersion product is selected depending on an intended use, and there is no particular restriction thereon. Specific examples include a polystyrene resin, a styrene
• the pigment dispersion product as a colorant for a toner containing toner base particles, which contain at least a binder resin, a colorant, a wax, etc.
• increase of the dispersion viscosity in a dispersion medium can be suppressed, so that handling in a production step for a toner becomes easy and the dispersibility of the colorant remains good, and therefore a yellow toner having high coloring power as well as a process for producing the yellow toner can be provided.
• a wax usable in the present invention there is no particular restriction on a wax usable in the present invention, and examples thereof include a petroleum wax, such as paraffin wax, a
• a derivative includes an oxide, and a block copolymer or a graft modified polymer with a vinyl monomer.
• examples further include an alcohol such as a higher aliphatic alcohol, a fatty acid such as stearic acid and palmitic acid, and a compound thereof, an acid amide, an ester, a. ketone, a hydrogenated castor oil and a derivative thereof, a vegetable wax, and an animal wax.
• an alcohol such as a higher aliphatic alcohol, a fatty acid such as stearic acid and palmitic acid, and a compound thereof, an acid amide, an ester, a. ketone, a hydrogenated castor oil and a derivative thereof, a vegetable wax, and an animal wax.
• the above may be used singly or in combination thereof.
• content with respect to 100 parts by mass of a binder resin is preferably in the range of 2.5 to 15.0 parts by mass, and more preferably in the range of 3.0 to 10.0 parts by mass. If the amount of a wax added is less than 2.5 parts by mass, oilless fusing becomes difficult, and if the amount exceeds 15.0 parts by mass, the amount of the wax in a toner particle is excessive and possible existence at a high
• charge control agent may be mixed, according to need, with toner base particles and used. By doing so, the triboelectric charge amount can be controlled
• a charge control agent As a charge control agent, a known agent can be used, and a charge control agent, which can offer
• substantially without soluble matter in an aqueous dispersing medium is especially preferable.
• Examples of a charge control agent, which controls a toner to negatively chargeable include a polymer or a copolymer having a sulfonic acid group, a sulfonic acid base or a sulfonic acid ester group, a salicylic acid derivative and a metal complex thereof, a
• monoazometallic compound an acetylacetone metallic compound, an aromatic oxycarboxylic acid, an aromatic mono- or poly-carboxylic acid and a metal salt thereof, an anhydride, esters, a phenol derivative such as bisphenol, a urea derivative, a metal-containing naphthoic acid compound, a boron compound, a
• quaternary ammonium salt a calixarene, and a resin- type charge control agent.
• Examples of a charge control agent, which controls a toner to positively chargeable include nigrosin and a nigrosin derivative modified by a fatty acid metal salt, etc. , a quaternary ammonium salt, such as a guanidine compound, an imidazole compound, a tributylbenzylammonium-1-hydroxy-4 -naphthosulfonic acid salt, and tetrabutylammonium tetrafluoroborate, and an analog thereof, such as an onium salt like a phosphonium salt and a lake pigment therefrom, a triphenylmethane dye and a lake pigment therefrom (as a laking agent: phosphotungstic acid, phosphomolybdic acid, phosphotungstomolybdic acid, tannic acid, lauric acid, gallic acid, ferricyanide , ferrocyanide, etc.), a metal salt of a higher fatty acid, a diorganot
• dicyclohexyltin borate and a resin-type charge control agent.
• the above may be used singly or in combinations of two or more thereof.
• An inorganic fine powder may be added externally as a flow agent to a toner according to the present
• an inorganic fine powder a fine powder of silica, titanium oxide, alumina, and a double oxide of the above, as well as the above after surface treatment can be used.
• Toner particles to be produced by a suspension polymerization process are produced, for example, as follows .
• polymerizable monomer composition is dispersed in an aqueous medium to form particles of the polymerizable monomer composition by granulation. Then a
• polymerizable monomer composition is polymerized in the aqueous medium to yield toner particles.
• the polymerizable monomer composition in the above step is preferably prepared by dispersing the colorant in a first polymerizable monomer to obtain a
• a colorant including a pigment composition according to the present invention is dispersed thoroughly in a first polymerizable monomer, and then the same is mixed together with another toner material with a second polymerizable monomer, so that a pigment can be present in a toner particle in a better dispersed condition.
• a known polymerization initiator can be named, and examples include an azo compound, an organic peroxide, an inorganic peroxide, an organometallic compound, and a photopolymerization initiator.
• More specific examples include an azo polymerization initiator, such as 2,2'- azobis ( isobutyronitrile) , 2,2' -azobis (2- methylbutyronitrile) , 2,2'-azobis ( 4-methoxy-2 , 4- dimethylvaleronitrile) , 2,2' -azobis (2, 4- dimethylvaleronitrile ) , and dimethyl-2 , 2 ' - azobis (isobutyrate) ; an organic peroxide
• polymerization initiator such as benzoyl peroxide, di- tert-butyl peroxide, tert-butyl
• an inorganic peroxide polymerization initiator such as potassium persulfate, and ammonium persulfate
• a redox initiator such as a hydrogen peroxide-ferrous iron system , a BPO-dimethylaniline system, and a cerium (IV) salt-alcohol system.
• a photopolymerization initiator include an acetophenone system, a benzoin ether system, and a ketal system. The above may be used singly or in combinations of two or more thereof.
• he concentration of the polymerization initiator is preferably in the range of 0.1 to 20 parts by mass, and more preferably in the range of 0.1 to 10 parts by mass with respect to 100 parts by mass of the
• a type of the polymerization initiator may be slightly different depending on a polymerization process, and used singly or in a mixture in reference to the 10 hour half-life
• polymerization process contains preferably a
• dispersion stabilizing agent As the dispersion stabilizing agent, a known inorganic or organic dispersion stabilizing agent can be used.
• examples of an inorganic dispersion stabilizing agent include calcium phosphate, magnesium phosphate, aluminum phosphate, zinc phosphate, magnesium carbonate, calcium carbonate, calcium hydroxide, magnesium hydroxide, aluminum hydroxide, calcium metasilicate, calcium sulfate, barium sulfate, bentonite, silica, and alumina.
• examples of an organic dispersion stabilizing agent include polyvinyl alcohol, gelatin, methylcellulose, methyl hydroxypropylcellulose, ethylcellulose, sodium salt of carboxymethylcellulose, and starch. Further, a nonionic, anionic, and
• cationic surfactant can be also used. Examples thereof include . sodium dodecyl sulfate, sodium
• potassium stearate potassium stearate, and calcium oleate.
• a poorly water soluble inorganic dispersion stabilizing agent which is soluble in an acid
• the dispersion stabilizing agent is preferably used at a mixture ratio in the range of 0.2 to 2.0 parts by mass with respect to 100 parts by mass of the
• an aqueous medium is preferably prepared by using water in the range of 300 to 3,000 parts by mass with respect to 100 parts by mass of the polymerizable monomer composition.
• soluble inorganic dispersion stabilizing agent is dispersed, is prepared in the present invention, a commercially available dispersion stabilizing agent may be dispersed as it is, however, the medium is preferably prepared by generating the poorly water soluble inorganic dispersion stabilizing agent in water under high speed agitation for obtaining a dispersion stabilizing agent particle having a uniform and fine particle diameter.
• the medium is preferably prepared by generating the poorly water soluble inorganic dispersion stabilizing agent in water under high speed agitation for obtaining a dispersion stabilizing agent particle having a uniform and fine particle diameter.
• a favorable dispersion stabilizing agent can be obtained by mixing an aqueous solution of sodium phosphate and an aqueous solution of calcium chloride under high speed agitation to form a fine particle of calcium phosphate.
• a suspension granulation process can also give favorable toner particles. Since there is no heating step in a production step of a
• Toner particles produced by the suspension granulation process are produced, for example, as follows.
• a solvent-containing composition is prepared by mixing a colorant including the pigment dispersion product, a binder resin, a wax, etc. in a solvent.
• a toner particle suspension is yielded by dispersing the solvent-containing composition in an aqueous medium for forming particles of the solvent- containing composition by granulation.
• toner particles can be obtained by removing the solvent by heating the yielded suspension, or under a reduced pressure .
• the solvent-containing composition in the above step is preferably prepared by dispersing the colorant in a first solvent to obtain a dispersion, and mixing the dispersion with a second solvent.
• a colorant including a pigment composition according to the present invention is dispersed thoroughly in a first solvent, and then the same is mixed together with another toner material with a second solvent, so that a pigment can be present in toner particles in a better dispersed condition.
• hydrocarbons such as toluene, xylene, and hexane
• halogen-containing organic compound such as toluene, xylene, and hexane
• hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, and carbon
• alcohols such as methanol, ethanol, butanol, and isopropyl alcohol
• polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, and triethylene glycol
• cellosolve family such as methyl cellosolve, and ethyl cellosolve
• ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone
• ethers such as .benzyl alcohol ethyl ether, benzyl alcohol isopropyl ether, and tetrahydrofuran
• esters such as methyl acetate, ethyl acetate, and butyl acetate. The above may be used singly or in a mixture of two or more thereof.
• a solvent which has a low boiling point and is capable of dissolving sufficiently the binder resin is preferably used among the above-listed
• he usage of the solvent is preferably in the range of 50 to 5,000 parts by mass, and more preferably in the range of 120 to 1,000 parts by mass with respect to 100 parts by mass of the binder resin.
• granulation process preferably contains a dispersion stabilizing agent.
• a dispersion stabilizing agent a known inorganic or organic dispersion
• inorganic dispersion stabilizing agent examples include calcium phosphate, calcium carbonate, aluminum hydroxide, calcium sulfate, and barium carbonate.
• organic dispersion stabilizing agent examples include a water- soluble polymer, such as polyvinyl alcohol,
• methylcellulose hydroxyethylcellulose, ethylcellulose, a sodium salt of carboxymethylcellulose, sodium
• surfactants including an anionic surfactant, such as sodium dodecylbenzenesulfonate, sodium
• octadecylsulfate sodium oleate, sodium laurate, and potassium stearate
• a cationic surfactant such as laurylamine acetate, stearylamine acetate, and
• lauryltrimethylammonium chloride a zwitterionic surfactant such as lauryldimethylamine oxide
• a nonionic surfactant such as- polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and
• the usage of the dispersing agent is preferably in the range of 0.01 to 20 parts by mass with respect to 100 parts by mass of the binder resin from a standpoint of the droplet stability of the solvent-containing composition in an aqueous medium.
• a yellow toner according to the present invention has preferably the weight-average particle diameter D4 of
• weight-average particle diameter D4 is 4.9 to 7.5 ⁇
• weight-average particle diameter D4 is 4.9 to 7.5 ⁇
• diameter D4 /number-average particle diameter Dl is 1.30 or less. If the percentage less than 4.0 ⁇ with respect to the value of weight-average particle diameter D4 increases, when applied to an
• the adjustment can be conducted by controlling the concentration of a dispersing agent used for the preparation of an aqueous dispersing medium, a stirring speed for a reaction, or a stirred reaction time.
• a toner by a grinding process may contain a binder resin and a colorant and if necessary, may further contain a magnetic material, a wax, a charge control agent, and other additives.
• toner by a grinding process according to the present invention can be produced by a production apparatus known to one skilled in the art, such as a blender, a heated kneading machine, and a classifier.
• a production apparatus known to one skilled in the art, such as a blender, a heated kneading machine, and a classifier.
• the above materials are mixed sufficiently in a blender, such as a Henschel mixer and a ball mill.
• a blender such as a Henschel mixer and a ball mill.
• the mixture is molten by a heated kneading machine, such as a roll, a kneader, and an extruder.
• a wax or a magnetic material is dispersed in resins which have been blended and kneaded each other. After cooled and solidified, grinding and
• classification are carried out to yield a toner.
• grinding process include a vinyl resin, a polyester resin, an epoxy resin, a polyurethane resin, a polyvinyl butyral resin, a terpene resin, a phenolic resin, an aliphatic or alicyclic hydrocarbon resin, and an aromatic petroleum resin, as well as a rosin or a modified rosin.
• a vinyl resin and a polyester resin are more preferable from viewpoints of electrification and fixing properties.
• a polyester resin is preferable, because its effect on
• the resins may be used singly or in combinations of
• the glass transition temperature is preferably 45 to 80°C, more preferably 55 to 70°C, and the number
• Mn average molecular weight
• Mw weight-average molecular weight
• the molar% ratio of alcohol component/acid component with respect to the entire components is especially preferably 45/55 to 55/45.
• the acid value is preferably 90 mgKOH/g or less, and more preferably 50 mgKOH/g or less.
• the hydroxyl value is preferably 50 mgKOH/g or less, and more preferably 30 mgKOH/g or less.
• the glass transition temperature of a polyester resin used in the present invention is preferably 50 to 75°C, and more preferably 55 to 65°C.
• the number-average molecular weight (Mn) is preferably
• he weight-average molecular weight (Mw) is preferably
• a resin particle dispersion, a colorant particle dispersion, or another toner component may be mixed together according to need.
• Toner particles are obtained via a step for
• Dispersions of respective particles may use a
• a colorant particle dispersion is prepared by
• a colorant particle can be dispersed by a known method using favorably a media-type
• disperser such as a rotational shear homogenizer, a ball mill, a sand mill, and Attritor, or a high
• Examples of a surfactant according to the present invention include a water-soluble polymer, an inorganic compound, and an ionic or nonionic
• an ionic surfactant which has a good dispersing property, is preferable, and
• the molecular weight of a surfactant is preferably 100 to 10,000 and more preferably 200 to 5,000.
• surfactant examples include a water- soluble polymer, such as polyvinyl alcohol,
• surfactants including an anionic
• surfactant such as sodium dodecylbenzenesulfonate, sodium octadecylsulfate, sodium oleate, sodium laurate, and potassium stearate; a cationic surfactant, such as laurylamine acetate and lauryltrimethylammonium
• lauryldimethylamine oxide and a nonionic surfactant, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene alkyl amine; and an inorganic compound, such as tricalcium
• a wax dispersion according to the present invention is prepared by dispersing a wax in an aqueous medium.
• the wax dispersion is prepared by a known process.
• a wax means a material used for the purpose of preventing offsetting when a toner is fixed.
• a wax used frequently include a hydrocarbon wax, such as low molecular weight polyethylene, low molecular weight polypropylene, a microcrystalline wax, and a paraffin wax; an oxidized product of a hydrocarbon wax or a block copolymer thereof such as an oxidized
• polyethylene wax such as a fatty acid ester wax, such as a carnauba wax, a Sasol wax, and a montanic acid ester wax; a partially or completely deoxidized fatty acid ester such as a deoxidized carnauba wax; a saturated straight-chain fatty acid, such as palmitic acid, stearic acid, and montanic acid; an unsaturated fatty acid, such as brassidic acid, eleostearic acid, and parinaric acid; a saturated alcohol, such as stearyl alcohol, aralkyl alcohol, behenyl alcohol, carnaubyl alcohol, ceryl alcohol, and melissyl alcohol; a fatty acid ester wax, such as a carnauba wax, a Sasol wax, and a montanic acid ester wax; a partially or completely deoxidized fatty acid ester such as a deoxidized carnauba wax; a saturated straight-chain fatty acid, such as palmitic acid, stea
• polyhydric alcohol such as sorbitol
• a fatty acid amide such as linoleic acid amide, oleic acid amide, and lauric acid amide
• a saturated fatty acid bisamide such as methylenebisstearic acid amide
• ethylenebiscapric acid amide ethylenebislauric acid amide, and hexamethylenebisstearic acid amide
• an unsaturated fatty acid amide such as ethylenebisoleic acid amide, hexamethylenebisoleic acid amide, ⁇ , ⁇ '- dioleyladipic acid amide, and N,N' -dioleylsebacic acid amide
• an aromatic bisamide such as m- xylenebisstearic acid amide, and ⁇ , ⁇ ' - distearylisophthalic acid amide
• an aliphatic metal salt generally called as a metallic soap
• a partial ester of a fatty acid and a polyhydric alcohol such as behenic acid monog
• a hydrocarbon wax preferable examples include a fatty acid ester wax, and a saturated alcohol.
• the above waxes may be used singly or, according to need, in combinations of two or more thereof.
• present invention is preferably 1 to 25 parts by mass, and more preferably 3 to 20 parts by mass with respect to 100 parts by mass of the toner particle. If the wax is less than 1 part by mass, the releasing effect of a wax decreases, while if the wax exceeds 25 parts by mass, the release property is satisfied, however, the developing property deteriorates so that adverse effects, such as sticking of a toner to a surface of a development sleeve or an electrostatic latent image carrier, tend to appear frequently.
• invention is preferably 50°C or more and 200°C or less, and more preferably 55°C or more and 150°C or less. If a wax has the melting point less than 50°C, the antiblocking property of a toner may decline, and if the melting point exceeds 200°C, the wax exuding property during fixing becomes poor and the release property in oilless fusing may be deteriorated.
• DSC differential scanning calorimetry
• the melting point of a wax is the
• the amount of a wax according to the present invention added is preferably in the range of 2.5 to 15.0 parts by mass, and more preferably in the range of 3.0 to 10.0 parts by mass with respect to 100 parts by mass of a binder resin. If the amount of a wax added is less than 2.5 parts by mass, oilless fusing becomes difficult, and if the amount exceeds 15.0 parts by mass, the amount of the wax in a toner particle is excessive and possible existence at a high
• a resin particle dispersion to be used in the present invention is prepared by dispersing resin particles in an aqueous medium.
• an aqueous medium means a medium containing water as a main component.
• Specific examples of an aqueous medium include water itself, water with a pH adjustor added, and water with an organic solvent added.
• a resin particle included in the resin particle dispersion insofar as it is a resin suitable for a toner having the following properties, however a thermoplastic binder having the glass transition temperature equal to or lower than the fixing
• styrenes such as styrene, p-chlorostyrene, and a- methylstyrene
• a vinyl group monomer such as methyl acrylate, ethyl . acrylate, n-propyl acrylate, lauryl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, acrylonitrile, and methacrylonitrile
• a vinyl ether monomer such as vinyl methyl ether and vinyl isobutyl ether
• a vinyl ketone monomer such as vinyl methyl ketone, vinyl ethyl ketone, and vinyl isopropenyl ketone
• a olefinic monomer such as ethylene, propylene, and butadiene
• a resin particle dispersion to be used in the present invention is prepared by dispersing a resin particle in an aqueous medium.
• the resin particle dispersion is prepared by a known process.
• a resin particle dispersion can be prepared by conducting an emulsion polymerization of the monomer using a surfactant, etc.
• the resin is dispersed in water together with an ionic surfactant and a polymer electrolyte, by a disperser such as a homogenizer.
• a resin particle dispersion may be prepared by a process, in which a surfactant is added to a resin and the mixture is then emulsified and dispersed in water by a disperser such as a homogenizer, or by a phase inversion emulsification process.
• a disperser such as a homogenizer, or by a phase inversion emulsification process.
• a particle in a resin particle dispersion is preferably 0.005 to 1.0 ⁇ , and more preferably 0.01 to 0.4 ⁇ . If the median diameter is 1.0 ⁇ or more, a toner particle with the weight-average particle diameter of 3.0 to 7.5 ⁇ , which is appropriate for a toner
• the average particle diameter of a resin particle can be measured by, for example, a dynamic light
• DLS light scattering method
• an average particle diameter means, unless otherwise specified, a volume basis 50% cumulative particle diameter (D50) measured by a dynamic light scattering method ( DLS ) /Laser-Doppler method at 20°C and a solid concentration of 0.01 mass-%, as described below.
• present invention is prepared by dispersing a colorant together with a surfactant in an aqueous medium.
• dispersions of pigment yellow 185 and a compound represented by the general formula (1) of the present invention are each prepared.
• a dispersion of a mixture of the pigment yellow 185 and the compound represented by the general formula (1) can be also prepared.
• colorant particles can be
• a media- type disperser such as a rotational shear homogenizer, a ball mill, a sand mill, and Attritor, or a high pressure collision type disperser can be preferably used.
• the content of a colorant is preferably 1 to 20 parts by mass with respect to 100 parts by mass of the resin. Below 1 part by mass, securement of an adequate toner concentration . may become difficult, and above 20 parts by mass, a colorant not any more contained in toner particles tends to increase.
• he amount of a surfactant used is with respect to 100 parts by mass of the colorant 0.01 to 10 parts by mass, preferably 0.1 to 5.0 parts by mass, and especially preferably 0.5 parts by mass to 3.0 parts by mass, because the surfactant can be removed easily from a toner particle. As a result, the amount of a surfactant used is with respect to 100 parts by mass of the colorant 0.01 to 10 parts by mass, preferably 0.1 to 5.0 parts by mass, and especially preferably 0.5 parts by mass to 3.0 parts by mass, because the surfactant can be removed easily from a toner particle. As a result, the amount of a surfactant used is with respect to 100 parts by mass of the colorant 0.01 to 10 parts by mass, preferably 0.1 to 5.0 parts by mass, and especially preferably 0.5 parts by mass to 3.0 parts by mass, because the surfactant can be removed easily from a toner particle. As a result, the amount of a surfactant used is with respect to 100 parts by mass of the colorant 0.
• examples thereof include an alkali, such as ammonia and sodium hydroxide, and an acid, such as nitric acid and citric acid.
• an aggregating agent according to the present invention there is no particular restriction on an aggregating agent according to the present invention, and examples thereof include an inorganic metallic salt, such as sodium chloride, magnesium carbonate, magnesium
• a stabilizer according to the present invention mainly a surfactant is named.
• a surfactant examples thereof include a water-soluble polymer, such as polyvinyl alcohol, methylcellulose,
• surfactants including an anionic surfactant, such as sodium dodecylbenzenesulfonate , sodium
• octadecylsulfate sodium oleate, sodium laurate, and potassium stearate
• a cationic surfactant such as laurylamine acetate and lauryltrimethylammonium chloride
• a zwitterionic surfactant such as
• lauryldimethylamine oxide and a nonionic surfactant, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene alkyl amine; and an inorganic compound, such as tricalcium
• the average particle diameter of a formed aggregation particle may be
• the regulation can be easily performed, for example, by setting or changing appropriately the temperature during the addition/mixing of an aggregating agent or the condition for the stirred mixing. Further, the pH adjustor, the surfactant, etc. may be added
• a toner particle is formed in a fusing step by heating the aggregated particles for fusion.
• the heating temperature may be between the glass
• transition temperature (Tg) of a resin contained in an aggregated particle and the degradation temperature of the resin.
• Tg transition temperature
• progress of aggregation is stopped by adding a surfactant, adjusting the pH, etc., and the temperature is raised by heating to the glass transition temperature of the resin in the resin particle or higher to cause the fusion and coalescence of the aggregated particles.
• a step for forming a core-shell structure in which a fine particle dispersion with dispersed fine particles is added and mixed with the aggregated particle so as to adhere the fine particles onto the aggregated particle, may be additionally included before or after the fusing step.
• a toner particle is obtained by cleaning, filtrating, drying, etc. a toner particle obtained after the fusing step under appropriate conditions.
• the toner particle is preferably cleaned thoroughly .
• cleaning is repeated until the electric conductivity of the filtrate decreases to 150 ⁇ / ⁇ or less. If the electric conductivity exceeds 150 ⁇ / ⁇ , the
• an inorganic granule such as silica, alumina, titania, and calcium carbonate
• a resin particle such as a vinyl resin, a polyester resin, and a silicone resin
• the inorganic granule and the resin particle act as an external additive of a flow aid, a cleaning aid, etc.
• the water content of a toner particle after drying is preferably 1.5 mass-% or less, and more preferably 1.0 mass-% or less.
• the charge control agent can be mixed according to need with toner base particles and used. By this means, the triboelectric charge amount can be controlled to an optimal value corresponding to a development system.
• a charge control agent a known agent can be used, and especially a charge control agent, which can offer particularly high charging speed and maintain stably a constant charge amount, is preferable. Further, if a toner is produced by a direct polymerization process, a charge control agent with low polymerization
• inhibitory property and substantially without soluble matter in an aqueous dispersing medium is especially preferable .
• Examples of a charge control agent, which controls a toner to negatively chargeable include a polymer or a copolymer having a sulfonic acid group, a sulfonic acid base or sulfonic acid ester group, a salicylic acid derivative and a metal complex thereof, a
• monoazometallic compound an acetylacetone metallic compound, an aromatic oxycarboxylic acid, an aromatic mono- or poly-carboxylic acid and a metal salt thereof, an anhydride, esters, a phenol derivative such as bisphenol, a urea derivative, a metal-containing naphthoic acid compound, a boron compound, a
• quaternary ammonium salt a calixarene, and a resin- type charge control agent.
• Examples of a charge control agent, which controls a toner to positively chargeable include nigrosin and a nigrosin derivative modified by a . fatty acid metal salt, etc., a quaternary ammonium salt, such as a guanidine compound, an imidazole compound, a
• tributylbenzylammonium-l-hydroxy-4-naphthosulfonic acid salt, and tetrabutylammonium tetrafluoroborate and an analog thereof, such as an onium salt like a phosphonium salt and a lake pigment therefrom, a triphenylmethane dye and a lake pigment therefrom (as a laking agent: phosphotungstic acid, phosphomolybdic acid, phosphotungstomolybdic acid, tannic acid, lauric acid, gallic acid, ferricyanide , ferrocyanide, etc.), a metal salt of a higher fatty acid, a diorganotin oxide, such as dibutyltin oxide, dioctyltin oxide, and dicyclohexyltin oxide, a diorganotin borate, such as dibutyltin borate, dioctyltin borate, and
• control agent The above may be used singly or in combinations of two or more thereof.
• An inorganic fine powder may be added externally as a flow agent to a toner according to the present
• an inorganic fine powder a fine powder of silica, titanium oxide, alumina, and a double oxide of the above, as well as the above after surface treatment can be used.
• a toner according to the present invention has
• weight-average particle diameter D4 preferably the weight-average particle diameter D4 of 4.0 to 9.0 ⁇ , and the ratio of the weight-average particle diameter D4 to the number-average particle diameter Dl (hereinafter also referred to as "weight- average particle diameter D4 /number-average particle diameter Dl" or "D4/D1") of 1.35 or less. More preferably the weight-average particle diameter D4 is 4.9 to 7.5 and the weight-average particle
• diameter D4 /number-average particle diameter Dl is 1.30 or less. If the percentage less than 4.0 ⁇ with respect to the value of weight-average particle diameter D4 increases, when applied to an .
• measured by a flow-type particle image analyzer for a toner according to the present invention is 0.930 to 0.995, and more preferably 0.960 to 0.990 from a standpoint that the transferability of a toner can be improved significantly.
• a toner according to the present invention may be any toner according to the present invention.
• a magnetic toner either a magnetic toner or a nonmagnetic toner. If used as a magnetic toner, a toner particle
• inventions may be mixed with a magnetic material.
• Such a magnetic material examples include an iron oxide, such as magnetite, maghemite, and ferrite, or an iron oxide containing another metal oxide, a metal, such as Fe, Co, and Ni, an alloy between the metal and a metal, such as Al, Co, Cu, Pb, Mg, Ni, Sn, Zn, Sb, Be, Bi, Cd, Ca, Mn, Se, Ti, , and V, and a mixture thereof.
• a liquid developer may be produced in such a manner that a toner having a binder resin and a
• the colorant is dispersed or dissolved in an electrical insulating carrier liquid.
• an auxiliary agent such as a charge control agent and a wax may be dispersed or dissolved in the liquid developer if necessary.
• the liquid developer may be prepared by a 2-stage process, by which a concentrated toner is firstly prepared and then the concentrate is diluted with an electrical insulating carrier liquid.
• a disperser used in the present invention there is no particular restriction on a disperser used in the present invention, and preferable examples include a media-type disperser, such as a rotational shear homogenizer, a ball mill, a sand mill, and
• Attritor and a high pressure collision type disperser.
• toner known colorants such as a pigment or a dye may be further added singly or in combinations of two or more thereof.
• a charge control agent used in the present invention there is no particular restriction on a charge control agent used in the present invention, insofar as the charge control agent is used for a liquid developer for electrostatic charge image development.
• the charge control agent includes cobalt naphthenate, copper naphthenate, copper oleate, cobalt oleate, zirconium octoate, cobalt octoate, sodium dodecylbenzene sulfonate, calcium dodecylbenzene sulfonate, soybean lecithin, and aluminum octoate.
• an organic solvent with the electrical resistance as high as 10 9 ⁇ -cm or more and the dielectric constant as low as 3 or less is used preferably.
• organic solvent with the electrical resistance as high as 10 9 ⁇ -cm or more and the dielectric constant as low as 3 or less
• Specific and preferable examples thereof include an aliphatic hydrocarbon solvent, such as hexane, pentane, octane, nonane, decane, undecane, and dodecane, Isopar H, G, K, L, and M (by ExxonMobil Chemical Company) , and Linealene Dimer A-20 and A-20H (by Idemitsu Kosan Co., Ltd.), which have the boiling point in a temperature range of 68 to 250°C.
• the above may be used singly or in combinations of two or more thereof to the extent that the viscosity of the system becomes not too high.
• the compound (20) was obtained by the same operation as in Example 19, except that the amine compound and the pyridone compound in Example 19 were changed to the amine compound (20-1) and the pyridone compound (20-2), respectively.
• a solution of 1.8 g of the amine compound (21-1) in 50 mL of methanol was cooled to 5°C, into which 1.3 mL of 35% hydrochloric acid was dropped.
• a solution of 0.4 g of sodium nitrite in 8 mL of water was dropped, the solution was stirred for 1 hour to obtain a diazotization solution.
• a yellow toner according to the present invention and a comparative yellow toner were produced by a process described below.
• the above composition was heated to 60°C and dissolved or dispersed homogeneously by a T . K. HOMO Mixer at 5,000 rpm, in which 10 parts of 2 , 2 ' -azobis (2 , 4- dimethylvaleronitrile ) as a polymerization initiator was dissolved to prepare a polymerizable monomer composition.
• the polymerizable monomer composition was added into the aqueous medium and granulated into particles for 15 min maintaining the rotation speed at 12,000 rpm. Thereafter the high speed agitator was switched to a stirrer with propeller blades, and the polymerization was continued at the liquid temperature of 60°C for 5 hours, then after raising the liquid temperature to 80°C continued for another 8 hours.
• a hydrophobic silica fine powder surface-treated by hexamethyldisilazane (number average primary particle diameter 7 nm)
• 0.15 parts of a rutile-type titanium oxide fine powder (number average primary particle diameter 45 nm)
• 0.50 parts of a rutile-type titanium oxide fine powder (number average primary particle diameter 200 nm) were mixed by a Henschel mixer (by Nippon Coke &
• Yellow toners (2) to (4) according to the present invention were obtained similarly as in Example 1 except that the compound (1) in Example 1 was changed to 6 parts of the compound (2), 3.6 parts of the compound (8), and 8 parts of the compound (15),
• Yellow toners (5) to (7) according to the present invention were obtained similarly as in Example 1 except that the usage of C. I. pigment yellow 185 was changed from 12 parts in Example 1 to 10 parts, and the compound (1) was changed to 2 parts of the
• a yellow toner (8) according to the present invention was obtained similarly as in Example 1 except that the usage of C. I. pigment yellow 185 was changed, from 12 parts in Example 1 to 8 parts, and the compound (1) was changed to 8 parts of the compound (13) .
• Yellow toners (23) to (25) according to the present invention were obtained similarly as in Example 1 except that the usage of C. I. pigment yellow 185 was changed from 12 parts in Example 1 to 9 parts, and the compound (1) was changed to 5 parts of the compound (19), 4 parts of the compound (21), and 7 parts of the compound (24), respectively.
• Example 1 similarly as in Example 1 except that the compound (1) in Example 1 was not used.
• Example 1 similarly as in Example 1 except that the compound (1) in Example 1 was changed to a comparative compound (1).
• a comparative yellow toner (CE3) was obtained similarly as in Example 1 except that the usage of C. I. pigment yellow 185 was changed from 12 parts in Example 1 to 10 parts, and the compound (1) was
• the median diameter based on volume of the colorant particle in the C. I. pigment yellow 185 dispersion was 0.2 ⁇ , and the concentration of the C. I. pigment yellow 185 dispersion was 10 mass-%.
• the median diameter based on volume of the colorant particle in the compound (3) dispersion was 0.2 ⁇ , and the concentration of the compound (3) dispersion was 10 mass-%.
• the temperature was raised to 80°C and stirring was continued for 120 min to obtain a fused spherical toner particle.
• the reaction product was filtered, and the filtered solid was washed with 720 parts of ion exchanged water by stirring for 60 min.
• the solution containing a toner particle was filtered and cleaning was repeated similarly until the electric conductivity of the filtrate decreased to 150 ⁇ / ⁇ or less. After drying by a vacuum drier, a toner base particle (2) was obtained .
• Yellow toners (10) to (12) according to the present invention were obtained similarly as in Example 1 except that the compound (3) in Example 9 was changed to 6 parts of the compound (5), 3.6 parts of the compound (10), and 8 parts of the compound (11), respectively .
• Yellow toners (13) to (15) according to the present invention were obtained similarly as in Example 1 except that the usage of C. I. pigment yellow 185 in Example 9 was changed to 9 parts, and the compound (3) was changed to 1.8 parts of the compound (4), 4.5 parts of the compound (12), and 7 parts of the
• a yellow toner (16) according to the present invention was obtained similarly as in Example 1 except that C. I. pigment yellow 185 in Example 9 was changed to 10 parts, and the compound (3) was changed to 10 parts of the compound (16) .
• Example 9 similarly as in Example 9 except that the compound (3) in Example 9 was not used.
• Example 9 similarly as in Example 9 except that the compound (3) in Example 9 was changed to the comparative compound (1) .
• a binder resin a polyester resin: Tg
• Yellow toners (18) to (20) according to the present invention were obtained similarly as in Example 17 except that the compound (6) in Example 17 was changed to 5 parts of the compound (11), 0.5 parts of the compound (14), and 2 parts of the compound (17), respectively.
• Yellow toners (21) and (22) according to the present invention were obtained similarly as in Example 17 except that the usage of C. I. pigment yellow 185 in Example 17 was changed to 4 parts, and the compound (6) was changed to 2 parts of the compound (7) and 3.5 parts of the compound (18), respectively.
• Yellow toners (29) and (30) according to the present invention were obtained similarly as in Example 17 except that the usage of C. I. pigment yellow 185 in Example 17 was changed to 7 parts, and the compound (6) was changed to 4 parts of the compound (23) and 5 parts of the compound (26) , respectively.
• Example 17 similarly as in Example 17 except that the compound (6) in Example 17 was not used.
• Example 17 similarly as in Example 17 except that the compound (1) in Example 17 was changed to the comparative compound ( 3 ) .
• Example 1 similarly as in Example 1 except that the usage of C. I. pigment yellow 185 was changed from 12 parts in Example 1 to 6 parts, and the usage of the compound (1) was changed from 1.2 parts to 7 parts.
• Example 1 similarly as in Example 1 except that the usage of C. I. pigment yellow 185 was changed from 12 parts in Example 1 to 8 parts, and the usage of the compound (1) was changed from 1.2 parts to 0.5 parts.
• Counter TA-II or Coulter Multisizer II (by Beckman Coulter, Inc.) as a measuring apparatus according to operating manuals of the apparatus.
• electrolytic solution an approx. 1% aqueous solution of sodium chloride was prepared using an EP grade sodium chloride.
• ISOTON-II by Coulter Scientific Japan
• Specific measuring procedures are: To 100 to 150 mL of the aqueous electrolytic solution are added as a dispersing agent 0.1 to 5 mL of a surfactant (preferably an
• the weight-average particle diameter (D4) of a toner particle was determined from the volume-based distribution of the toner particle (the median value of each channel is defined as the
• D4/D1 is less than 1.30 (very good granulation property)
• D4/D1 is not less than 1.30 but less than 1.35
• D4/D1 is not less than 1.35 (poor granulation property)
• particle projected area means an area of a
• peripheral of particle projected image is defined as the length of an outline formed by connecting the edge points of the toner particle image.
• the circularity is an index showing unevenness of a particle, and gives 1.000 if a particle is perfectly spherical, and the circularity ⁇ gives a smaller value if the surface shape becomes more complex.
• Examples 26 to 28, and Comparative Examples 4 to 5), and toners by a grinding process (Examples 17 to 22, Examples 29 to 30, and Comparative Examples 6 to 7) different in production processes, a yellow toner obtainable according to the present invention is superior in terms of the granulation property compared to a corresponding comparative yellow toner,
• LBP image forming apparatus
• CCG developing blade in a process cartridge
• OD (Y) yellow optical density OD (Y) at a grey-scale with the maximum toner coating amount.
• Example 1 Compound (1) 1.81 A 4.8 A
• Example 2 Compound (2) 1.60 A 4.4 A
• Example 5 Compound (3) 1.60 A 4.6 A
• Example 8 8 Compound (13) 1.71 A 3.8 A
• Example 10 10 Compound (5) 1.61 A 2.6 A
• Example 12 Compound (1 1 ) 1.64 A 3.5 A
• Example 13 Compound (4) 1.66 A 2.9 A
• Example 15 15 Compound (9) 1.67 A 3.2 A
• Example 17 Compound (6) 1.69 A 4.2 A
• Example 18 16 Compound (1 1) 1.79 A 2.1 A
• Example 19 19 Compound (14) 1.62 A 4.0 A
• Example 22 22 Compound (18) 1.71 A 3.1 A
• Example 24 24 Compound (21) 1.69 A 3.2 A
• Example 25 25 Compound (24) 1.81 A 2.6 A
• Example 26 Compound (20) 1.80 A 3.1 A
• Example 27 Compound (22) 1.75 A 3.8 A
• Example 28 28 Compound (25) 1.68 A 2.2 A
• Example 30 Compound (26) 1.75 A 2.9 A
• a yellow toner obtainable according to the present invention is superior in terms of both of optical density and light resistance compared to a corresponding comparative yellow toner. Especially concerning the light
• composition ratio according to the present invention significant effect can be recognized by the use of a composition ratio according to the present invention.
• a factor which promotes degradation, may affect a surface layer to deteriorate only the surface layer.
• a degradation promoting factor cannot reach a pigment inside the aggregate.
• a degraded portion of the surface layer conceivably acts as a protective film for the pigment inside the aggregate to enhance the light resistance.
• a dye is dissolved or dispersed uniformly in a medium.
• a compound represented by the general formula (1) has conceivably entered somehow between the micro-dispersed C. I. pigment yellow 185.
• a compound represented by the general formula (1) can be protected by C. I. pigment yellow 185 against the degradation promoting factor, so that the light resistance of the compound represented by the general formula (1) is conceivably enhanced.

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