Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
  • C09B67/0085—Non common dispersing agents
  • C09B67/009—Non common dispersing agents polymeric dispersing agent
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
  • C08F212/02—Monomers containing only one unsaturated aliphatic radical
  • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
  • C08F212/06—Hydrocarbons
  • C08F212/08—Styrene
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/14—Esterification
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0046—Mixtures of two or more azo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
  • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
  • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/10—Printing inks based on artificial resins
  • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• • 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
  • G03G9/08788—Block polymers
• • 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
  • G03G9/08791—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by the presence of specified groups or side chains
• • 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
  • G03G9/09—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
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/0914—Acridine; Azine; Oxazine; Thiazine-;(Xanthene-) 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
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/0924—Dyes characterised by specific substituents
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2438/00—Living radical polymerisation
  • C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2810/00—Chemical modification of a polymer
  • C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority

Definitions

• the present invention relates to a compound having an azo skeleton structure, a pigment dispersant containing the above compound, a pigment composition containing the pigment dispersant, a pigment dispersion containing the pigment composition, and a toner.
• an azo compound including a
• PTL 2 styrene/acrylic-based high molecular portion
• magenta pigment in combination the dispersibility thereof is enhanced, and coloring properties and charging properties of a toner are improved (PTL 4).
• a toner which contains a polymer including sodium styrene sulfonate as a monomer unit, a phthalocyanine pigment, and a binder resin (PTL 5) .
• the present invention provides a compound and a pigment dispersant, each of which is able to improve the dispersibility of pigments of various colors, such as yellow, magenta, cyan, and black colors, in a non-aqueous solvent.
• the present invention also provides a pigment composition, a pigment dispersion, and a toner, each of which has a good coloring power.
• Ar represents an aryl group
• Ar and Ri to R 3 satisfy at least one of the following conditions (i) and (ii) :
• Ar has a linking group which is bonded to a carbon atom in the aryl group and is constituting a bonding moiety with the polymer;
• At least one of Ri to R 3 has a linking group constituting a bonding moiety with the polymer.
• Ri represents a hydrogen atom, an amino group, an alkyl group, a phenyl group, or an aralkyl group
• R 2 represents a hydrogen atom, a sulfonic acid group, a CONR 4 R 5 group, or a COOR 6 group,
• R 3 represents an alkyl group, a phenyl group, a hydroxyl group, a NR 7 R 8 group, a CONR9R10 group, a COORn group, a CH 2 COORi 2 group, or a C 2 H 4 COOR 13 group,
• R 4 , R 5 , and R 7 to Rio each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group, and
• R 6 and R to R 13 each independently represent a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, or a cation forming a salt with a carboxylic acid anion.
• R 14 represents a hydrogen atom or an alkyl group
• R i5 represents a phenyl group, a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group .
• a second aspect of the present invention relates to a pigment dispersant containing the compound described above.
• invention relates to a pigment composition containing the pigment dispersant described above and a pigment.
• a fourth aspect of the present invention relates to a pigment dispersion containing the pigment composition described above and a non-aqueous solvent.
• a fifth aspect of the present invention relates to a toner including toner particles which contain a binder resin and a colorant, and the colorant includes the pigment composition described above.
• the compound and the pigment dispersant of the present invention are able to improve the dispersibility of individual color pigments, such as yellow, magenta, cyan, and black pigments, in a non-aqueous solvent.
• the pigment composition, the pigment dispersion, and the toner of the present invention are able to have an excellent coloring power.
• Fig. 1 is a view showing a 13 C NMR spectrum of a compound (101) of the present invention measured in CDC1 3 at room temperature and 150 MHz.
• Fig. 2 is a view showing a 13 C NMR spectrum of a compound (141) of the present invention measured in CDC1 3 at room temperature and 150 MHz.
• Fig. 3 is a view showing a 13 C NMR spectrum of a compound (142) of the present invention measured in CDC1 3 at room temperature and 150 MHz.
• the compound of the present invention is a compound including a partial structure represented by the following formula (1) and a polymer which has monomer units each represented by the following formula (2) .
• Ar represents an aryl group
• Ar and Ri to R 3 satisfy at least one of the following conditions (i) and (ii) :
• Ar has a linking group which is bonded to a carbon atom in the aryl group and is constituting a bonding moiety with the polymer;
• At least one of Ri to R 3 has a linking group constituting a bonding moiety with the polymer.
• Ri represents a hydrogen atom, an amino group, an alkyl group, a phenyl group, or an aralkyl group
• R 2 when R 2 has not the linking group, R 2 represents a hydrogen atom, a sulfonic acid group, a CONRR 5 group, or a COOR 6 group, when R 3 has not the linking group, R 3 represents an alkyl group, a phenyl group, a hydroxyl group, a NR 7 R 8 group, a CONR 9 R 10 group, a COOR u group, a CH 2 COORi 2 group, or a
• R 4 , R 5 , and R 7 to Rio each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group, and
• R 6 and R to Ri 3 each independently represent a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, or a cation forming a salt with a carboxylic acid anion.
• R i4 represents a hydrogen atom or an alkyl group
• R15 represents a phenyl group, a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group.
• the partial structure represented by the above formula (1) may also be referred to as "azo skeleton structure” in some cases.
• the polymer having the monomer units each represented by the above formula (2) may also be referred to as "high molecular portion” in some cases.
• the compound including the polymer which has the monomer units each represented by the above formula (2) and the partial structure represented by the above formula (1) may also be referred to as
• linking group partial structure represented by the above formula (1) and which constitutes the bonding moiety with the polymer may be simply referred to as "linking group" in some cases.
• the compound having an azo skeleton structure includes an azo skeleton structure which is represented by the above formula (1) and which has a high affinity to various pigments and a high molecular portion (polymer) having the monomer units which are each represented by the above formula (2) and which have a high affinity to a nonaqueous solvent.
• amino group represented by Ri in the above formula (1) for example, there may be mentioned an amino group, a methyl amino group, an ethyl amino group, an N,N- dimethyl amino group, an N-ethyl-N-phenyl amino group, N,N- diphenyl amino group, an acetyl amino group, a benzoyl amino group, or a propionyl amino group.
• alkyl group represented by Ri in the above formula (1) for example, there may be mentioned a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n- pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a cyclohexyl group.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n- pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group,
• aralkyl group represented by Ri in the above formula (1) for example, a benzyl group or a phenethyl group may be mentioned.
• the amino group, the alkyl group, the phenyl group, and the aralkyl group represented by Ri in the above formula (1) each may be further substituted by a substituent as long as the affinity to pigments is not considerably impaired.
• a substituent which may be used, for example, an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxyl group, a carboxylic acid ester group, or a
• carboxylic acid amide group may be mentioned.
• Ri preferably represents a hydrogen atom.
• the sulfonic acid group represented by R 2 in the above formula (1) may be either a S0 3 H group or an ion pair formed from a sulfonate anion and a cation.
• a cation for example, an alkali metal ion or a quaternary ammonium ion may be mentioned.
• the alkali metal ion for example, a lithium ion, a sodium ion, or a potassium ion may be mentioned.
• quaternary ammonium ion for example, a tetramethyl ammonium ion, a tetrabutyl ammonium ion, or a trirriethyl stearyl ammonium ion may be mentioned.
• alkyl group represented by R 4 and R 5 in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-but
• aralkyl group represented by R 4 and R 5 in the above formula (1) for example, a benzyl group or a phenethyl group may be mentioned.
• the alkyl group, the phenyl group, and the aralkyl group represented by R 4 and R5 in the above formula (1) each may be further substituted by a substituent as long as the affinity to pigments is not considerably impaired.
• a substituent which may be used, for example, an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group may be mentioned.
• alkyl group represented by R.6 in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-but
• aralkyl group represented by R 6 in the above formula (1) for example, a benzyl group or a phenethyl group may be mentioned.
• an alkali metal ion or a quaternary ammonium ion may be mentioned.
• an alkali metal ion for example, a lithium ion, a sodium ion, or a potassium ion may be mentioned.
• quaternary ammonium ion for example, a tetramethyl ammonium ion, a tetrabutyl ammonium ion, or a trimethyl stearyl ammonium ion may be mentioned.
• R 2 in the above formula (1) may arbitrarily
• R 2 preferably represents a sulfonic acid group or a CONR4R5 group, and R 4 and R 5 in the CONR4R5 group each more preferably represent a hydrogen atom.
• alkyl group represented by R 3 in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-buty
• alkyl group represented by R 7 and RQ in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-but
• aralkyl group represented by R 7 and Rs in the above formula (1) for example, a benzyl group or a phenethyl group may be mentioned.
• the alkyl group, the phenyl group, and the aralkyl group represented by R 7 and R 8 in the above formula (1) each may be further substituted by a substituent as long as the affinity to pigments is not considerably impaired.
• a substituent which may be used, for example, an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group may be mentioned.
• alkyl group represented by R 9 and Rio in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-buty
• aralkyl group represented by R 9 and Rio in the above formula (1) for example, a benzyl group or a phenethyl group may be mentioned.
• the alkyl group, the phenyl group, and the aralkyl group represented by Rg and Rio in the above formula (1) each may be further substituted by a substituent as long as the affinity to pigments is not considerably impaired.
• a substituent which may be used, for example, an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl ' group, a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group may be mentioned.
• alkyl group represented by Rn in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-buty
• aralkyl group represented by R in the above formula (1) for example, a benzyl group or a
• phenethyl group may be mentioned.
• an alkali metal ion or a quaternary ammonium ion may be mentioned.
• the alkali metal ion for example, a lithium ion, a sodium ion, or a potassium ion may be mentioned.
• quaternary ammonium ion for example, a tetramethyl ammonium ion, a tetrabutyl ammonium ion, or a trimethyl stearyl ammonium ion may be mentioned.
• alkyl group represented by R 12 in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• aralkyl group represented by R12 in the above formula (1) for example, a benzyl group or a
• phenethyl group may be mentioned.
• an alkali metal ion or a quaternary ammonium ion may be mentioned.
• an alkali metal ion for example, a lithium ion, a sodium ion, or a potassium ion may be mentioned.
• quaternary ammonium ion for example, a tetramethyl ammonium ion, a tetrabutyl ammonium ion, or a trimethyl stearyl ammonium ion may be mentioned.
• alkyl group represented by R i3 in the above formula (1) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-
• aralkyl group represented by R 13 in the above formula (1) for example, a benzyl group or a
• phenethyl group may be mentioned.
• an alkali metal ion or a quaternary ammonium ion may be mentioned.
• an alkali metal ion for example, a lithium ion, a sodium ion, or a potassium ion may be mentioned.
• quaternary ammonium ion for example, a tetramethyl ammonium ion, a tetrabutyl ammonium ion, or a trimethyl stearyl ammonium ion may be mentioned.
• R 3 in the above formula (1) may arbitrarily
• an alkyl group is preferable.
• an NR 7 R 9 group or a COORn group is preferable.
• aryl group in Ar in the above formula (1) a phenyl group or a naphthyl group may be mentioned.
• Ar in the above formula (1) may further have a substituent as long as the affinity to pigments is not considerably impaired.
• this substituent for example, an alkyl group, a C00R 2 i group, an OR 22 group, a CONR23R24 group, or the linking group may be mentioned.
• R 2 i to R24 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group.
• Ar in the above formula (1) preferably has at least one linking group as the substituent, and it is more preferable that Ar in the above formula (1) has at least one linking group, and the other functional groups of Ar are all hydrogen atoms.
• Ar in the above formula (1) preferably represents a phenyl group. That is, the partial structure represented by the above formula (1) preferably indicates the structure represented by the following formula (3) .
• Ri to R 3 and Ri 6 to R20 satisfy at least one of the following conditions (iii) and (iv):
• Ri 6 to R 2 o has a linking group constituting a bonding moiety with the polymer
• At least one of Ri to R 3 has a linking group constituting a bonding moiety with the polymer.
• R x represents a hydrogen atom, an amino group, an alkyl group, a phenyl group, or an aralkyl group
• R 2 when R 2 has not the linking group, R 2 represents a hydrogen atom, a sulfonic acid group, a CONR 4 R 5 group, or a C00R 6 group,
• R 3 when R 3 has not the linking group, R 3 represents an alkyl group, a phenyl group, a hydroxyl group, a NR 7 R 8 group, a CONR 9 R 10 group, a COORn group, a CH 2 COORi 2 group, or a
• R 4 , R 5 , and R 7 to Rio each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group,
• R 6 and Rn to R i3 each independently represent a hydrogen atom, an alkyl group, a phenyl group, an aralkyl group, or a cation which forms a salt with a carboxylic acid anion,
• Ri6 to R20 each has not the linking froup
• Ri6 to R20 each independently represent a hydrogen atom, an alkyl group, a COOR21 group, an OR 22 group, or a CONR23R24 group
• R21 to R 2 each independently represent a hydrogen atom, an alkyl group, a phenyl group, or an aralkyl group.
• Ri to R 3 in the above formula (3) each indicate the same meaning as that of each of Ri to R 3 in the above formula (1).
• alkyl group represented by R 16 to R 24 in the above formula (3) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-but
• aralkyl group represented by R 2 i to R24 in the above formula (3) for example, a benzyl group or a phenethyl group may be mentioned.
• alkyl group represented by R 2 i in the above formula (3) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-
• aralkyl group represented by R 2 i in the above formula (3) for example, a benzyl group or a
• phenethyl group may be mentioned.
• alkyl group represented by R 22 in the above formula (3) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-buty
• aralkyl group represented by R 22 in the above formula (3) for example, a benzyl group or a
• phenethyl group may be mentioned.
• alkyl group represented by R23 and R 2 in the above formula (3) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-but
• aralkyl group represented by R 2 3 and R 24 in the above formula (3) for example, a benzyl group or a phenethyl group may be mentioned.
• Ri6 to R 2 o in the above formula (3) may arbitrarily represent the linking group or one of the aforementioned hydrogen atom, alkyl group, COOR 2 i group, OR 22 group, and CONR 23 R 2 4 group.
• at least one of Ri6 to R 20 in the above formula (3) preferably represents the linking group, and the others each preferably represent a hydrogen atom.
• structure represented by the above formula (3) is preferably bonded to the polymer at one or two positions.
• the linking group which is a part of the partial structure represented by the formula (1) and which constitutes the bonding moiety with the polymer preferably has a carboxylic acid ester bond or a carboxylic acid amide bond.
• the bonding moiety including the functional group is referred to as the linking group.
• linking group for example, the following may be mentioned.
• Li to L 8 each represent a bonding position to a carbon atom in the high molecular portion having the monomer units each represented by the above formula (2) .
• "**" in the above formulas Li to L 8 each represent a bonding position to a carbon atom in an aromatic ring of Ar of the partial structure represented by the above formula (1) or a bonding position to a carbon atom or a nitrogen atom in a heterocyclic ring including Ri to R 3 .
• alkyl group represented by Ri 4 in the above formula (2) for example, a linear, a branched, or a cyclic alkyl group, such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, or a cyclohexyl group, may be mentioned.
• a linear, a branched, or a cyclic alkyl group such as a methyl group, an ethyl group, an n- propyl group, an n-butyl group, an n-pentyl group, an n- hexyl group, an isopropyl group, an isobutyl group, a sec- butyl group, a tert-buty
• Ri4 in the above formula (2) may arbitrarily represent one of the aforementioned hydrogen atom and alkyl group. Among those mentioned above, in view of
• a linear or a branched ester group such as a methyl ester group, an ethyl ester group, an n-propyl ester group, an isopropyl ester group, an n-butyl ester group, an isobutyl ester group, a sec-butyl ester group, a tert-butyl ester group, an octyl ester group, a nonyl ester group, a decyl ester group, an undecyl ester group, a dodecyl ester group, a hexadecyl ester group, an octadecyl ester group, an eicosyl ester group, a docosyl ester group, a 2-ethylhexyl ester group, a phenyl ester group, or a 2-
• the carboxylic acid amide group represented by R 15 in the above formula (2) for example, there may be mentioned a linear or a branched amide group, such as an N- methyl amide group, an ⁇ , ⁇ -dimethyl amide group, an N-ethyl amide group, an ⁇ , ⁇ -diethyl amide group, an N-isopropyl amide group, an N, N-diisopropyl amide group, an N-n-butyl amide group, an N, -di-n-butyl amide group, an N-isobutyl amide group, an N, N-diisobutyl amide group, an N-sec-butyl amide group, an N, -di-sec-butyl amide group, an N-tert- butyl amide group, an N-octyl amide group, an N,N-dioctyl amide group, an N-nonyl
• the phenyl group, carboxyl group, carboxylic acid ester group, and carboxylic acid amide group represented by R 15 in the above formula (2) may be further substituted.
• this substituent which may be used, for example, there may be mentioned an alkoxy group, such as a methoxy group or an ethoxy group; an amino group, such as an N-methyl amino group or an ⁇ , ⁇ -dimethyl amino group; an acyl group such as an acetyl group; or a halogen atom, such as a fluorine atom or a chlorine atom.
• Ri5 in the above formula (2) may arbitrarily represent one of the aforementioned phenyl group, carboxyl group, carboxylic acid ester group, and carboxylic acid amide group.
• a phenyl group, a carboxylic acid ester group, or a carboxylic acid amide group is preferable.
• the above high molecular portion is able to control the affinity to a dispersion medium by changing the ratio of the monomer unit represented by the above formula (2).
• the dispersion medium is a non-polar solvent such as styrene
• the ratio of the monomer unit in which Rxs in the above formula (2) represents a phenyl group is preferably
• the ratio of the monomer unit in which R 15 in the above formula (2) represents a carboxyl group, a carboxylic acid ester group, or a carboxylic acid amide group is preferably increased in view of the affinity to the dispersion medium.
• the molecular weight of the above high molecular portion is preferably 500 or more in terms of the number average
• the molecular weight of the high molecular portion is preferably 200,000 or less. Furthermore, in view of easy manufacturing, the number average molecular weight of the high molecular portion is more preferably 2,000 to 50,000.
• branched aliphatic chains at terminals of the dispersant.
• branched aliphatic chains may also be introduced at the terminals, and the dispersibility may be improved in some cases.
• the positions of the azo skeleton structures of the compound having an azo skeleton structure may be randomly located in the compound or may be localized at one terminal thereof by forming one block or a plurality of blocks.
• the number of the partial structures (azo skeleton structures) in the above compound having an azo skeleton structure is, in consideration of the balance between the affinity to pigments and the affinity to dispersion media, preferably 0.5 to 10 and more preferably 0.5 to 5 with respect to 100 monomer units forming the high molecular portion .
• the compound having an azo skeleton structure may be synthesized in accordance with a known method.
• [Ri to R 3 in formulas (7) and (8) each indicate the same meaning as that of . each of Ri to R 3 in the above formula (1) .
• Ar x in a formula (6) and the formula (8) represents an arylene group.
• ⁇ represents a high molecular portion obtained by polymerizing a polymerizable monomer which forms the monomer unit represented by the above formula (2) .
• Qi in the formulas (6) and (8) represents a linking group which reacts with ⁇ so as to link the partial structure
• n in the formulas (6) and (8) represents an integer value.
• an aniline derivative represented by the formula (6) is allowed to react with a compound (7) through a diazo coupling step 1 to synthesize an azo
• step 1 First, the step 1 will be described.
• a known method may be used in the step 1.
• the aniline derivative (6) is allowed to react in a methanol solvent, with a diazotizing agent, such as sodium nitrite or nitrosyl sulfuric acid, in the presence of an inorganic acid, such as hydrochloric acid or sulfuric acid, so as to synthesize a corresponding diazonium salt.
• a diazotizing agent such as sodium nitrite or nitrosyl sulfuric acid
• an inorganic acid such as hydrochloric acid or sulfuric acid
• aniline derivative (6) Many types of the above aniline derivative (6) are available on the market and can be easily obtained. In addition, this aniline derivative may be easily synthesized by a known method.
• this step 1 may be performed without using a solvent, in order to prevent rapid reaction progress, this step is preferably performed in the presence of a solvent.
• a solvent although any solvents may be used as long as not inhibiting the reaction, the following solvents may be mentioned by way of example.
• an alcohol such as methanol or ethanol
• an ester such as methyl acetate, ethyl acetate, or propyl acetate
• an ether such as diethyl ether
• tetrahydrofuran, or dioxane a hydrocarbon, such as benzene, toluene, xylene, hexane, or heptane; a halogen-containing hydrocarbon, such as dichloromethane, dichloroethane, or chloroform; an amide, such as N, N-dimethylformamide, N- methylpyrrolidone, or N, N-dimethylimidazolidinone; a nitrile, such as acetonitrile or propionitrile; an acid, such as formic acid, acetic acid, or propionic acid; or water may be mentioned.
• a hydrocarbon such as benzene, toluene, xylene, hexane, or heptane
• a halogen-containing hydrocarbon such as dichloromethane, dichloroethane, or chloroform
• an amide such as N, N-dimethylformamide, N-
• the usage is preferably set to 1.0 to 20 times the mass of the compound represented by the above formula (6).
• This step 1 is generally performed in a temperature range of -50°C to 100°C and is generally completed within 24 hours .
• radical polymerization is preferably used in view of easy manufacturing.
• the radical polymerization may be performed by irradiation of radiation or laser beams, the use of a radical polymerization initiator, the use of a
• radical polymerization initiator any material which can generate radicals and can initiate a polymerization reaction may be used, and a compound which generates radicals by heat, light, radiation, or an
• oxidation-reduction reaction may be selected.
• an azo polymerization initiator an organic peroxide polymerization initiator, an inorganic peroxide polymerization initiator, an organometallic compound polymerization initiator, and a photopolymerization initiator may be mentioned.
• the azo polymerization initiator an organic peroxide polymerization initiator, an inorganic peroxide polymerization initiator, an organometallic compound polymerization initiator, and a photopolymerization initiator may be mentioned.
• the azo polymerization initiator an organic peroxide polymerization initiator
• an inorganic peroxide polymerization initiator an organometallic compound polymerization initiator
• a photopolymerization initiator a photopolymerization initiator
• azo polymerization initiators 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 4 , 4 ' -azobis ( 4-cyanovaleric acid) ; organic peroxide polymerization initiators, such as benzoyl peroxide, di-tert-butyl peroxide, tert- butylperoxyisopropyl carbonate, tert-hexyl peroxybenzoate, and tert-butyl peroxybenzoate; inorganic peroxide
• polymerization initiators such as potassium peroxide and ammonium peroxide
• redox initiators such as a hydrogen peroxide-ferrous-based compound, a benzoyl peroxide-dimethyl aniline-based compound, and a cerium (IV) salt-alcohol-based compound
• photopolymerization initiators such as a benzophenone, a benzoin ether, an acetophenone, and a thioxanthone, may be mentioned by way of example.
• At least two of those radical polymerization initiators may be used in combination, if necessary.
• the usage of the polymerization initiator is, with respect to 100 parts by mass of the polymerizable monomer, preferably adjusted in a range of 0.1 to 20 parts by mass so as to obtain a copolymer having a targeted molecular weight distribution .
• the high molecular portion represented by the above Pi may be manufactured by any one of solution polymerization, suspension polymerization, emulsion
• solution polymerization is preferably performed in a solvent which dissolves individual components used in manufacturing.
• a solvent either a polar organic solvent or a non-polar organic solvent may be used.
• the polar solvent for example, there may be mentioned an alcohol, such as methanol, ethanol, or 2-propanol; a ketone, such as acetone or methyl ethyl ketone; an ether, such as tetrahydrofuran or diethyl ether; an ethylene glycol
• the non-polar organic solvent for example, toluene or xylene may be mentioned.
• solvents having a boiling point in a range of 100°C to 180°C are more
• polymerization temperature may vary depending on the type of polymerization initiator to be used and is not particularly limited; however, in particular, polymerization is generally performed in a temperature range of -30°C to 200°C and more preferably in a temperature range of 40°C to 180°C.
• the molecular weight distribution and the molecular structure of the high molecular portion represented by the above Pi can be controlled by known methods.
• a high molecular portion Pi having controlled molecular weight distribution and molecular structure can be manufactured, for example, by a method which uses an addition-fragmentation chain transfer agent
• polymerization initiator for example, by Masami Kamigaito, and two others, "Chemical Reviews", (USA), American Chemical Society, 2001, Vol. 101, pp. 3,689 to 3,746]; an RAFT method which uses a dithiocarboxylic acid ester and/or a xanthate compound as a polymerization initiator (for example, PCT Japanese Translation Patent Publication No. 2000-515181); an MADIX method (for example, International Publication No.
• a know method may be used.
• the compound having an azo skeleton structure in which the linking group has a carboxylic acid ester bond can be synthesized.
• the high molecular portion P x having a carboxyl group and an azo compound (8) having a hydroxyl group the compound having an azo skeleton structure in which the linking group has a carboxylic acid ester bond can be synthesized.
• the high molecular portion P x having a carboxyl group and an azo compound (8) having a hydroxyl group the compound having an azo skeleton structure in which the linking group has a carboxylic acid ester bond can be synthesized.
• this step 2 may be carried out without using s solvent, in order to prevent rapid reaction progress, this step is preferably performed in the presence of a solvent.
• a solvent any solvents may be used as long as not inhibiting the reaction, and for example, the
• an ether such as diethyl ether
• tetrahydrofuran, or dioxane a hydrocarbon, such as benzene, toluene, xylene, hexane, or heptane; a halogen-containing hydrocarbon, such as dichloromethane, dichloroethane, or chloroform; an amide, such as N, N-dimethylformamide, N,N- dimethylacetamide, N-methylpyrrolidone, or N,N- dimethylimidazolidinone; or a nitrile, such as acetonitrile or propionitrile, may be mentioned by way of example.
• a hydrocarbon such as benzene, toluene, xylene, hexane, or heptane
• a halogen-containing hydrocarbon such as dichloromethane, dichloroethane, or chloroform
• an amide such as N, N-dimethylformamide, N,N- dimethylacetamide, N
• At least two of the above solvents may be used by mixing.
• a mixing ratio therebetween may be arbitrarily determined.
• the usage of the solvent may be arbitrarily
• the amount is preferably in a range of 1.0 to 20 times the mass of the compound represented by the general formula (6).
• This step 2 is generally performed at a temperature range of 0°C to 250°C and is generally completed within 24 hours .
• the azo compound (10) having a polymerizable functional group is copolymerized with a polymerizable monomer forming the monomer unit represented by the above formula (2), the compound having an azo skeleton structure can be synthesized.
• the azo compound (10) having a polymerizable functional group can be synthesized.
• a vinyl group-containing compound (9) in which Q 2 represents a carboxyl group and an azo compound (8) in which Qi represents a hydroxyl group an azo compound (10) in which Q 3 represents a linking group having a carboxylic acid ester bond can be synthesized.
• an azo compound (10) in which Q 3 represents a linking group having a carboxylic acid amide bond can be synthesized.
• step 4 by copolymerization between the compound (10) having a polymerizable functional group and the polymerizable monomer forming the monomer unit represented by the above formula (2) , the compound having an azo skeleton structure
• [Ri to R 3 , Ari, , and n in a formula (8) each indicate the same meaning as that of each of R x to R 3 , Ari, Q lf and n in the formula (8) in the scheme of the above method (i) .
• Q 5 in a formula (12) represents a linking group which is formed by a reaction between Q x in the formula (8) and Q 4 in a formula
• A represents a
• step 5 by the use of a method similar to that of the step 2 of the above method (i) , the azo compound
• the azo compound (12) including a halogen atom can be synthesized.
• the halogen atom-containing compound (11) in which Q 4 represents a substituent having a carboxyl group and an azo compound (8) in which Qi represents a substituent having an amino group the azo compound (12) including a halogen atom can be synthesized.
• halogen atom-containing compound (11) having a carboxyl group described above for example, the following may be mentioned.
• halogen atom-containing compound (11) having a hydroxyl group for example, there may be mentioned 1- chloroethanol, 1-bromoethanol, 1-iodoethanol , 1- chloropropanol, 2-bromopropanol , 2-chloro-2-propanol, 2- bromo-2-methylpropanol, 2-phenyl-l-bromoethanol, or 2- phenyl-2-iodoethanol .
• a metal catalyst used in the ATRP method is not particularly limited, at least one type of transition metal selected from those of the Groups 7 to 11 of the periodic table is preferable.
• a redox catalyst redox conjugated complex
• a low valence complex and a high valence complex change reversibly
• the following may be mentioned.
• cuprous chloride for example, cuprous bromide, cuprous iodide, or cuprous cyanide may be preferably used.
• an organic ligand is generally used.
• tributylphosphine may be mentioned by way of example.
• an aliphatic polyamine such as N, , N ' , N" , "-pentamethyldiethylenetriamine, is preferable in view of easy manufacturing.
• a high molecular portion which has the monomer units each represented by the above formula (2) and which is bonded in advance to an aryl group having an amino group and an intermediate which is a pyridone analog are separately synthesized and are then processed by diazo- coupling, so that a compound having an azo skeleton
• Step 7 Step 8 s e P
• step 9 in which the high molecular portion (15) having an amino group-containing arylene group is diazo- coupled with an intermediate (7) which is a pyridone analog, the compound having an azo skeleton structure is synthesized.
• step 7 by the use of a method similar to that of the step 2 of the above method (i) , the high
• molecular portion (14) having a nitro group-containing arylene group can be synthesized. For example, by a
• molecular portion (14) having a nitro group-containing arylene group in which the linking group is a carboxylic acid ester bond can be synthesized.
• a reaction between the high molecular portion Pi having a carboxyl group and a nitro group-containing arylene group (13) in which Q 6 represents an amino group a high molecular portion (14) having a nitro group-containing arylene group in which the linking group is a carboxylic acid amide bond can be synthesized.
• a known method may be used.
• a method which uses a metal compound or the like for example, there may be used a method disclosed in "Experimental Chemistry Course” (Jikken Kagaku Kouza, in Japanese), Maruzen Co., Ltd., Second edition, Volume 17-2, pp. 162 to 179.
• a catalytic hydrogenation method for example, there may be used a method disclosed in "New Experimental Chemistry Course” (Shin Jikken Kagaku
• this step 8 may be carried out without using a solvent, in order to prevent rapid reaction progress, this step is preferably performed in the presence of a solvent.
• a solvent any solvents may be used as long as not inhibiting the reaction, and for example, the
• an alcohol such as methanol, ethanol, or propanol
• an ester such as methyl acetate, ethyl acetate, or propyl acetate
• an ether such as diethyl ether
• tetrahydrofuran or dioxane
• a hydrocarbon such as benzene, toluene, xylene, hexane, or heptane
• an amide such as N, N-dimethylformamide, N-methylpyrrolidone, or N,N- dimethylimidazolidinone, may be mentioned by way of example.
• At least two of the above solvents may be used by mixing, and when the solvents are to be used by mixing, a mixing ratio may be arbitrarily determined.
• the usage of the solvent may be arbitrarily determined in accordance with the solubility of the substrate, in view of the reaction rate, an amount in a range of 1.0 to 20 times the mass of the compound
• This step is generally performed at a temperature range of 0°C to 250°C and is generally completed within 24 hours .
• step 8 by the use of a method similar to that of the step 2 in the above method (i) , the high
• molecular portion (15) having an amino group-containing arylene group can be synthesized.
• step 9 by the use of a method similar to that of the step 1 of the above method (i), the compound having an azo skeleton structure can be synthesized.
• isolation and the purification methods for example, a re-crystallization method and a re- precipitation method, each of which uses an organic solvent, and a column chromatography using silica gel may be
• the pigment dispersant of the present invention preferably contains this compound having an azo skeleton structure.
• the compound having an azo skeleton structure may be used alone, or at least two types thereof may be used in combination.
• the pigment composition of the present invention contains the above compound having an azo skeleton structure and a pigment.
• This pigment composition may be used for a paint, an ink, a toner, and a resin molded article .
• a pigment contained in the pigment composition of the present invention, a pigment may be appropriately selected from the yellow pigments described, for example, in "Organic Pigments Handbook" published in 2006 (written and published by Isao Hashimoto) .
• quinoxaline pigment may be mentioned by way of example.
• a monoazo pigment, a bisazo pigment, a polyazo pigment, and an isoindoline pigment may be preferably used.
• an acetoacetanilide pigment such as C.I. Pigment Yellow 74, 93, 128, 155, 175, or 180, or an isoindoline pigment, such as C.I. Pigment Yellow 139 or 185, is preferable.
• C.I. Pigment Yellow 155 or 185 is more preferable .
• the yellow pigments mentioned above may be used alone, or at least two types thereof may be used by mixing [0156] As a yellow colorant contained in the pigment composition of the present invention, as long as not
• a known yellow colorant may be used together with the above yellow pigment.
• the colorant to be used together therewith for example, a condensed azo compound, an isoindoline compound, an anthraquinone compound, an azo metal complex, a methine compound, a quinophthalone compound, and an allylamide compound may be mentioned.
• a pigment contained in the pigment composition of the present invention, a pigment may be appropriately selected from the magenta pigments described for example, in "Organic Pigments Handbook" published in 2006 (written and published by Isao Hashimoto) .
• Organic Pigments Handbook published in 2006 (written and published by Isao Hashimoto) .
• pigment a disazonaphthol pigment, a perylene pigment, a thioindigo pigment, a diketopyrrolopyrrole pigment, a
• naphthol AS pigment or a BONA lake pigment may be mentioned.
• a quinacridone pigment, a diketopyrrolopyrrole pigment, a naphthol AS pigment, and a BONA lake pigment are preferable.
• the following compounds are preferable since having a high affinity to the compound having an azo skeleton structure of the present invention. That is, a quinacridone pigment represented by the following formula (16), a diketopyrrolopyrrole pigment represented by the following formula (17), and a naphthol AS pigment and a BONA lake pigment, each of which is represented by the following formula (18), are preferable.
• R 30 to R 37 each independently represent a hydrogen atom, a chlorine atom, or a methyl group.
• R 38 to R 47 each independently represent a hydrogen atom, a chlorine atom, a t-butyl group, a cyano group, or a phenyl group.
• R 48 to R 50 each independently represent a hydrogen atom, a methoxy group, a methyl group, a nitro group, a chlorine atom, a N, N-dimethylaminosulfonyl group, a sulfonic acid group, a sulfonic acid salt group, or a CONHR 52 group;
• R51 represents an amino group, a carboxylic acid group, a carboxylic acid salt group, or a CONHR53 group; and
• R 52 and R 53 each independently represent a hydrogen atom or a phenyl group.
• quinacridone pigment represented by the above formula (16) for example, C.I. Pigment Red 202, 122, 192, or 209 may be mentioned.
• R30 to R 37 in the above formula (16) may arbitrarily represent one of the aforementioned substituents . Among those mentioned above, in view of the affinity to the
• R 30 , R 32 to R 34 , R 36 and R 37 each preferably
• R 31 and R 35 each independently represent a hydrogen atom, a chlorine atom, or a methyl group .
• diketopyrrolopyrrole pigment represented by the above formula (17) for example, C.I. Pigment Red 255, 254, or 264 may be mentioned.
• R 38 to R47 in the above formula (17) may arbitrarily represent one of the aforementioned substituents .
• R 38 , R39, R41 to R 44 , R 6 , and R 47 each preferably represent a hydrogen atom
• R 40 and R 45 each preferably represent a hydrogen atom or a phenyl group.
• Naphthol AS pigment represented by the above formula (18) for example, C.I. Pigment Red 2, 3, 5, 6, 7, 23, 150, 146, 184, or 269 may be mentioned.
• BONA lake pigment represented by the above formula (18) for example, C.I. Pigment Red 48: 2, 48: 3, 48: 4 or 57: 1 may be mentioned.
• R 48 to R 50 preferably represents a CONHR 52 group
• R 5 i preferably represent a CONHRs 3 group
• Rs 3 preferably represents a hydrogen atom in view of the affinity to the compound having an azo skeleton structure of the present invention.
• a quinacridone pigment such as C.I. Pigment Red 122 or 202
• a Naphthol AS pigment such as C.I. Pigment Red 255, 264, or 150
• the above magenta pigments may be used alone, or at least two types thereof may be used by mixing.
• magenta colorant to be contained in the pigment composition of the present invention as long as not degrading the dispersibility of the pigment, a known magenta colorant may be used together with the aforementioned magenta pigment.
• magenta colorant As the magenta colorant to be used together,
• anthraquinone compound a basic dye lake compound, a
• benzimidazolone compound a thioindigo compound, and a perylene compound may be mentioned.
• a cyan pigment to be contained in the pigment composition of the present invention a phthalocyanine pigment represented by the following formula (19) may be preferably used.
• R 54 to R 57 each independently represent a hydrogen atom, an alkyl group, a sulfonic acid group, or a sulfonic acid salt group, and M represents a metal atom or a hydrogen atom.
• phthalocyanine pigment represented by the above formula (19) for example, there may be mentioned C.I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6, 16, 17, 17: 1, 68, 70, 75, 76, or 79.
• the pigments mentioned above may be used alone, or at least two types thereof may be used by mixing.
• a known cyan colorant may be used together with the aforementioned pigment .
• the cyan colorant to be used together therewith for example, there may be mentioned C.I. Pigment Blue 1, 1: 2, 1: 3, 2, 2: 1, 2: 2, 3, 4, 5, 6, 7, 8, 9, 9: 1, 10, 10: 1, 11, 12, 13, 14, 18, 19, 20, 21, 22, 23, 24, 24: 1, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 36: 1, 52, 53, 56, 56: 1, 57, 58, 59, 60, 61, 61: 1, 62, 63, 64, 65, 66, 67, 69, 71, 72, 73, 74, 77, 78, 80, 81, 82, 83, or 84.
• colorant may also be used in order to adjust the hue. For example, when C.I. Pigment Green 7 is mixed with C.I.
• carbon black may be preferably used as a black colorant to be contained in the pigment composition of the present invention.
• carbon black used in the present invention is not particularly limited, for example, carbon black obtained by a manufacturing method, such as a thermal method, an acetylene method, a channel method, a furnace method, or a lamp black method, may be used.
• primary particle diameter is preferably 14 to 80 nm and more preferably 25 to 50 nm.
• the average primary particle diameter of carbon black may be measured by taking an enlarged photo thereof using a scanning electron microscope.
• a DBP oil absorption amount of the carbon black used in the present invention is not particularly limited, the amount is preferably 30 to 200 mL/100 g and more preferably 40 to 150 mL/100 g.
• the coloring power of a printed image can be further
• the DBP oil absorption amount of carbon black indicates the amount of DBP (dibutyl phthalate) absorbed by 100 g of carbon black and may be measured in accordance with "JIS K6217" .
• the pH of carbon black may be measured with a pH electrode using a mixed liquid containing carbon black and distilled water.
• the specific surface area of carbon black is not particularly limited, 300 m 2 /g or less is preferable, and 100 m 2 /g or less is more preferable.
• the addition amount of the compound having an azo skeleton structure can be further decreased.
• the specific surface area of carbon black is a BET specific surface area and may be measured in accordance with "JIS K4652".
• the above carbon black may be used alone, or at least two types thereof may be used by mixing.
• a black colorant used in the present invention as long as not degrading the dispersibility of the carbon black, a known black colorant may be used together with the above carbon black.
• black colorant for example, there may be mentioned C.I. Pigment Black 1, 10, or 31; C.I. Natural Black 1, 2, 3, 4, 5, or 6; or activated carbon may be mentioned.
• the black colorant to be contained in the pigment composition of the present invention may be used together with a known magenta colorant, cyan colorant, or yellow colorant for color toning.
• pigments other than the yellow pigment, magenta pigment, cyan pigment, or carbon black as described above may also be used as long as having an
• the pigments which can be used in the present invention are not limited to those mentioned above.
• Pigments which are not processed by purification, control of crystalline system and particle diameter, and surface treatment, that is, crude pigments, may also be used as long as being formed from raw materials corresponding to the pigments mentioned above.
• a processed pigment composition may also be used.
• a composition ratio [ (pigment) : (compound having an azo skeleton structure) ] of the pigment in the pigment composition to the compound having an azo skeleton structure on a mass basis is preferably 100: 0.1 to 100: 100 and more preferably 100: 0.5 to 100: 20.
• the pigment composition may be manufactured by either a wet method or a dry method. Since the compound having an azo skeleton structure of the present invention has a high affinity to a non-aqueous solvent, a wet method which can easily manufacture a uniform pigment composition is preferable. In particular, the pigment composition may be formed as described below.
• a pigment dispersant is dissolved in a dispersion medium together with a resin as needed, and while stirring is preformed, a pigment powder is gradually added thereto so as to be sufficiently blended well with the medium.
• a dispersing machine such as a kneader, a roll mill, a ball mill, a paint shaker, a dissolver, an attritor, a sand mill, or a high-speed mill, a mechanical sharing force is applied.
• a dispersing machine such as a kneader, a roll mill, a ball mill, a paint shaker, a dissolver, an attritor, a sand mill, or a high-speed mill.
• dispersant can be adsorbed on the surface of the pigment, and the pigment can be finely dispersed in the form of stable and uniform fine particles.
• auxiliary agents may be further added during manufacturing.
• a surfactant for example, a surfactant, a dispersant, a filler, a
• a standardizing agent a resin, a wax, ah antifoaming agent, an antistatic agent, an anti-dust agent, an extender, a shading colorant, a preservative, a dry suppressing agent, a rheology controller, a wetting agent, an antioxidant, a UV absorber, and a photostabilizer may be used alone, or at least two thereof may be used in combination.
• the pigment dispersant of the present invention may be added in advance when a crude pigment is manufactured.
• the pigment dispersion of the present invention contains the pigment composition and a non-aqueous solvent functioning as a dispersion medium.
• the pigment dispersion may be either a dispersion in which the above pigment composition is dispersed in a non-aqueous solvent or a dispersion in which individual constituent elements of the pigment composition are dispersed in a non-aqueous solvent.
• the pigment dispersion may be formed as
• a pigment dispersant and a resin are dissolved as needed in a dispersion medium, and while stirring is
• a pigment or a pigment composition powder is gradually added thereto so as to be sufficiently blended with the dispersion medium.
• a dispersing machine such as a ball mill, a paint shaker, a dissolver, an attritor, a sand mill, or a high-speed mill, when a mechanical sharing force is applied, the pigment can be dispersed in the form of stable and uniform fine particles.
• the non-aqueous solvent functioning as a dispersion medium of the pigment dispersion of the present invention is selected in accordance with targeted application of the pigment dispersion and is not particularly limited.
• an ester such as methyl acetate, ethyl acetate, or propyl acetate
• a hydrocarbon such as hexane, octane, petroleum ether, cyclohexane, benzene, toluene, or xylene
• a halogenated hydrocarbon such as carbon tetrachloride, trichloroethylene, or
• the non-aqueous solvent functioning as a dispersion medium of the pigment dispersion of the present invention may be a polymerizable monomer.
• the polymerizable monomer As the polymerizable
• styrene a-methylstyrene, a-ethylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, p- methoxystyrene, p-phenylstyrene, p-chlorostyrene, 3,4- dicholorstyrene, p-ethylstyrene, 2 , -dimethylstyrene, p-n- butylstyrene, p-tert-butylstyrene, p-n-hexylstyrene, p-n- octylstyrene, p-n-nonylstyrene, p-n-decylstyrene, p-n- dodecylstyrene, ethylene, propylene, but
• methacrylate behenyl methacrylate, phenyl methacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl
• acrylate dodecyl acrylate, 2-ethylhexyl acrylate, stearyl acrylate, behenyl acrylate, 2-chloroethyl acrylate, phenyl acrylate, vinyl methyl ether, vinyl ethyl ether, vinyl isobutyl ether, vinyl methyl ketone, vinyl hexyl ketone, methyl isopropenyl ketone, vinyl naphthalene, acrylonitrile, methacrylonitrile, and acryl amide may be mentioned by way of example.
• a resin which can be dissolved in the non-aqueous solvent may be selected in accordance with targeted
• a polystyrene resin a polystyrene copolymer, a poly (acrylic acid) resin, a
• poly (methacrylic acid) resin a polyacrylate resin, a polymethacrylate resins, an acrylate copolymer, a
• methacrylate copolymer a polyester resin, a poly (vinyl ether) resin, a poly (vinyl alcohol) resin, a poly (vinyl butyral) resin, a polyurethane resin, and a polypeptide resin may be mentioned.
• a polyester resin a poly (vinyl ether) resin, a poly (vinyl alcohol) resin, a poly (vinyl butyral) resin, a polyurethane resin, and a polypeptide resin
• a poly (vinyl ether) resin a poly (vinyl alcohol) resin, a poly (vinyl butyral) resin, a polyurethane resin, and a polypeptide resin
• a polyurethane resin a polyurethane resin
• a polypeptide resin a polypeptide resin
• at least two types of those resins may be used by mixing.
• a toner of the present invention includes toner particles containing a binder resin and a colorant.
• the above pigment composition is used as the colorant, so that the dispersibility of the pigment in the toner particles is maintained in a preferable state, so that a toner having a high coloring power can be obtained.
• binder resin a known resin which is generally used may be used.
• styrene-methacrylic acid copolymer a styrene-acrylic acid copolymer
• a polyester resin an epoxy resin
• a styrene- butadiene copolymer a styrene-butadiene copolymer
• the toner particles may be directly obtained by polymerizing a polymerizable monomer in
• a styrene monomer such as styrene, a- methylstyrene, a-ethylstyrene, o-methylstyrene, m- methylstyrene, p-methylstyrene, o-ethylstyrene, m- ethylstyrene, or p-ethylstyrene
• a methacrylate monomer such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, octyl methacrylate, dodecy.l methacrylate, stearyl methacrylate, behenyl
• 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 acrylate, acrylonitrile, or amide acrylate; or an olefin monomer, such as butadiene, isoprene, or cyclohexene, may be mentioned by way of example.
• Tg glass transition temperature
• the binder resin when a non-polar resin, such as a polystyrene, and a polar resin, such as a polyester resin or a polycarbonate resin, are used in combination, distribution of additives, such as a colorant, a charge control agent, and a wax, in the toner particles can be controlled.
• a non-polar resin such as a polystyrene
• a polar resin such as a polyester resin or a polycarbonate resin
• additives such as a colorant, a charge control agent, and a wax
• the polar resin is added.
• the polar resin is added in accordance with the balance in polarity between a polymerizable monomer composition to be formed into the toner particles and an aqueous medium. As a result, for example, since a thin layer of the polar resin is formed on the surface of the toner particle, the resin
• the colorant can be preferably distributed in the toner particle.
• a cross-linking agent may be used when the binder resin is synthesized.
• cross-linking agent a bifunctional cross- linking agent and a cross-linking agent having at least three functions may be used.
• divinylbenzene bis (4- acryloxypolyethoxyphenyl) propane, ethylene glycol diacrylate, 1,3—butylene glycol diacrylate, 1, 4-butanediol diacrylate, 1, 5-pentanediol diacrylate, 1 , 6-hexanediol diacrylate, neopentyl glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol
• diacrylate diacrylates of polyethylene glycol #200, #400, and #600, dipropylene glycol diacrylate, polypropylene glycol diacrylate, polyester diacrylate, and dimethacylates which are obtained from the above diacrylates by using a dimethacrylate function group instead of the diacrylate function group.
• cross-linking agent having at least three functions, for example, there may be mentioned
• pentaerythritol triacrylate trimethylolethane triacrylate, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, oligoester acrylate, and methacrylates thereof; 2, 2-bis (4- (methacryloxy) phenyl) propane, diallyl phthalate, triallyl cyanurate, triallyl isocyanurate, and triallyl trimellitate .
• the amount of the cross- linking agent is preferably 0.05 to 10 parts by mass and more preferably 0.1 to 5 parts by mass.
• a wax may also be used when the binder resin is synthesized.
• the wax for example, there may be mentioned a petroleum wax or a derivative thereof, such as a paraffin wax, a microcrystalline wax, or petrolatum; a montan wax or a derivative thereof; a hydrocarbon wax by a Fischer-Tropsch method or a derivative thereof; a polyolefin wax or a derivative thereof, such as a polyethylene wax; or a natural wax or a derivative thereof, such as a carnauba wax or a candelilla wax.
• a petroleum wax or a derivative thereof such as a paraffin wax, a microcrystalline wax, or petrolatum
• a montan wax or a derivative thereof such as a hydrocarbon wax by a Fischer-Tropsch method or a derivative thereof
• a polyolefin wax or a derivative thereof such as a polyethylene wax
• a natural wax or a derivative thereof such as a carnauba wax or a candelilla wax.
• an alcohol such as a higher aliphatic alcohol, a fatty acid, such as stearic acid or palmitic acid, a fatty acid amide, a fatty acid ester, a hardened castor oil or its derivative, a vegetable wax, or an animal wax may also be mentioned. Those waxes mentioned above may be used alone or in combination.
• the addition amount of the above wax is preferably 2.5 to 15.0 parts by mass and more preferably 3.0 to 10.0 parts by mass.
• the addition amount of the wax is within the range described above, the fixing properties and the charging properties can be further improved.
• a charge control agent may be contained in the toner particles, if necessary.
• the toner may contain a charge control agent.
• the charge control agent a known agent may be used.
• a charge control agent which has a high charging speed and which can stably maintain a predetermined charge amount is preferable.
• a charge control agent which has a low polymerization inhibition property and which contains substantially no substances soluble in an aqueous medium is particularly preferable.
• charge control agent a negative-charging charge control agent and a positive-charging charge control agent may be used.
• the negative-charging charge control agent for example, the following may be used.
• the positive-charging charge control agent for example, the following may be used.
• a nigrosine or a nigrosine modified by a fatty acid metal salt or the like, a guanidine compound, an imidazole compound, or a quaternary ammonium salt, such as tributyl benzyl ammonium-l-hydroxy-4-naphthol sulfonate or tetrabutylammonium tetrafluoroborate, may be mentioned by way of example.
• Those charge control agents may be used alone or in combination.
• an inorganic fine powder may be added to the toner particles.
• the inorganic fine powder for example, silica, titanium oxide, alumina, or a composite oxide thereof may be used, and in addition, powders obtained by performing a surface treatment on those mentioned above may also be used.
• toner particles As a method for manufacturing toner particles, a pulverization method, a suspension polymerization method, suspension granulation method, and an emulsion
• the toner particles are preferably formed by a suspension
• toner particles manufactured by a suspension polymerization method may be manufactured as described below.
• composition of the present invention a polymerizable monomer, a wax component, a polymerization initiator, and the like are mixed together to prepare a polymerizable monomer composition. Next, this polymerizable monomer
• composition is dispersed in an aqueous medium to form
• the polymerizable monomer in the particles of the polymerizable monomer composition is polymerized in the aqueous medium to obtain the toner particles.
• the above polymerizable monomer composition is preferably prepared in such a way that after a dispersion in which the above colorant is dispersed in a first
• this dispersion is mixed with a second polymerizable monomer. That is, after the above pigment composition is sufficiently dispersed in the first polymerizable monomer, this dispersion is mixed with the second polymerizable monomer together with other toner materials, so that the pigment can be more preferably
• polymerization initiator used in the above suspension polymerization a known polymerization initiator may be mentioned.
• an organic peroxide polymerization initiator an organic peroxide polymerization initiator, an inorganic peroxide polymerization initiator, an organic metal compound polymerization initiator, or a
• photopolymerization initiator may be mentioned.
• 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) , or dimethyl 2,2'- azobis ( isobutyrate)
• an organic peroxide polymerization initiator such as benzoyl peroxide, di-tert-butyl peroxide, tert-butyl peroxyisopropylmonocarbonate, tert-hexyl
• inorganic peroxide polymerization initiator such as
• potassium persulfate or ammonium persulfate, may be any potassium persulfate.
• Those polymerization initiators may be used alone or in combination.
• the addition amount of the above polymerization initiator is, with respect to 100 parts by mass of the polymerizable monomer, preferably in a range of 0.1 to 20 parts by mass and more preferably in a range of 0.1 to 10 parts by mass.
• the polymerization initiators mentioned above may be used alone, or at least two thereof may be used by mixing.
• the aqueous medium used in the above suspension polymerization preferably contains a dispersion stabilizer.
• a dispersion stabilizer known inorganic and organic dispersion stabilizers may be used.
• inorganic dispersion stabilizer for example, there may be mentioned 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, or alumina.
• organic dispersion stabilizer for example, there may be mentioned a poly(vinyl alcohol), a gelatin, a methyl cellulose, a methyl hydroxypropyl cellulose, an ethyl cellulose, a sodium carboxymethyl cellulose, or a starch.
• a nonion, an anion, and a cation surfactant may also be used.
• a nonion, an anion, and a cation surfactant may also be used.
• a poor water soluble inorganic dispersion stabilizer which is soluble in an acid is preferably used.
• the amount of this dispersion stabilizer is preferably set in a range of 0.2 to 2.0 parts by mass.
• the aqueous medium is preferably prepared using 300 to 3,000 parts by mass of water with respect to 100 parts by mass of the polymerizable monomer composition.
• the above poor water soluble inorganic dispersion stabilizer is preferably generated and prepared in water under highspeed stirring conditions.
• a preferable dispersion stabilizer can be
• preferable toner particles may also be obtained. Since a manufacturing process of the suspension granulation method includes no heating step, compatibility between a resin and a wax component, which occurs when a low melting-point wax is used, can be suppressed, and hence, a decrease in glass transition temperature caused by this compatibility can be prevented. In addition, in the suspension granulation method, since the degree of freedom of selecting a toner material to be used as the binder resin is high, a polyester resin which is generally considered advantageous for the fixing properties may be easily used as a primary component. Hence, when a toner having a resin composition to which a suspension polymerization method cannot be applied is manufactured, this suspension granulation method is an advantageous manufacturing method.
• the toner particles manufactured by the above suspension granulation method are formed, for example, by the following way. First, a colorant containing the pigment composition of the present invention, a binder resin, a wax, and the like are mixed together in a solvent to prepare a solvent composition. Next, this solvent composition is dispersed in an aqueous medium to form particles of the solvent composition, so that a toner particle suspension liquid is obtained. Subsequently, the suspension liquid thus obtained is heated or is placed under a reduced
• the solvent composition in the above step is preferably prepared by mixing a second solvent with a dispersion in which the above colorant is dispersed in a first solvent. That is, since the above colorant is
• the pigment can be more preferably dispersed in the tonner particles.
• a hydrocarbon such as toluene, xylene, or hexane
• a halogen-containing hydrocarbon such as methylene chloride, chloroform, dichloroethane, trichloroethane, or carbon tetrachloride
• an alcohol such as methanol, ethanol, butanol, or isopropyl alcohol
• a polyalcohol such as ethylene glycol, propylene glycol, diethylene glycol, or triethylene glycol
• a cellosolve such as methyl cellosolve or ethyl cellosolve
• a ketone such as acetone, methyl ethyl ketone, or methyl isobutyl ketone
• an ether such as benzyl alcohol ethyl ether, benzyl alcohol isopropyl ether, or tetrahydrofuran
• an ester such as methyl acetate, eth
• Those mentioned above may be used alone, or at least two types thereof may be used by mixing. Among those mentioned above, in order to easily remove the solvent in the above toner particle suspension liquid, a solvent which has a low boiling point and which can sufficiently dissolve the above binder resin is preferably used.
• the usage of the solvent is, with respect to 100 parts by mass of the binder resin, preferably in a range of 50 to 5,000 parts by mass and more preferably in a range of 120 to 1,000 parts by mass.
• the aqueous medium used in the above suspension granulation method preferably contains a dispersion
• dispersion stabilizer known inorganic and organic dispersion stabilizers may be used.
• inorganic dispersion stabilizer for example, calcium phosphate, calcium carbonate, aluminum hydroxide, calcium sulfate, or barium carbonate may be mentioned.
• a water-soluble polymer such as a poly (vinyl alcohol) , a methyl cellulose, a hydroxyethyl cellulose, an ethyl cellulose, a sodium carboxymethyl cellulose, a sodium polyacrylate, or a sodium polymethacrylate
• an anionic surfactant such as sodium dodecylbenzenesulfonate, sodium octadecyl sulfate, sodium oleate, sodium laurate, or potassium stearate
• a cationic surfactant such as lauryl amine acetate, stearyl amine acetate, or lauryl trimethyl ammonium chloride
• an amphoteric surfactant such as lauryl dimethyl amine oxide
• a nonion surfactant such a polyoxyethylene alkyl ether, a polyoxyethylene alkylphenyl ether, or a polyoxyethylene alky
• the usage of the above dispersion stabilizer is, with respect to 100 parts by mass of the binder resin, preferably in a range of 0.01 to 20 parts by mass in view of the droplet stability of the solvent composition in the aqueous medium.
• the weight average particle diameter (hereinafter referred to as "D4" in some cases) of the toner is preferably 3.0 to 15.0 um and more preferably 4.0 to 12.0 um.
• D4 the weight average particle diameter of the toner
• the ratio (hereinafter also referred to as "D4/D1”) of D4 to the number average particle diameter (hereinafter referred to as "Dl”) is preferably 1.35 or less and more preferably 1.30 or less.
• D4/D1 is in the above range, the generation of fogging and the decrease in transfer efficiency can be further suppressed, and an image having a high resolution can be easily obtained.
• methods for adjusting D4 and Dl of the toner may vary depending on the method for manufacturing toner particles.
• the adjustment may be performed by controlling the concentration of the dispersion stabilizer used in the preparation of the aqueous medium, the reaction stirring rate, the reaction stirring time, and/or the like.
• the toner of the present invention may be either a magnetic toner or a non-magnetic toner.
• the toner particles forming the tdner of the present invention may be mixed with a magnetic substance.
• a known substance may be used, and for example, iron oxides, such as magnetite, maghemite, and ferrite, may be mentioned.
• the average particle diameter of those magnetic substances is preferably 0.1 to 2 ⁇ and more preferably 0.1 to 0.3 ⁇ .
• the coercive force, the saturation magnetization, and the remnant magnetization are preferably 1.6 to 12 KA/m, 5 to 200 Am 2 /kg (preferably 50 to 100 Am 2 /kg) , and 2 to 20 Am 2 /kg, respectively, in view of developing properties of the toner.
• the addition amount of the magnetic substance mentioned above is, with respect to 100 parts by mass of the binder resin, preferably 10 to 200 parts by mass and more preferably 20 to 150 parts by mass.
• the molecular weight of the compound having an azo skeleton structure was calculated based on polystyrene conversion by a size exclusion chromatography (SEC) .
• SEC size exclusion chromatography
• a molecular weight calibration curve prepared using standard polystyrene resins [manufactured by Tosoh Corp., TSK standard polystyrenes F-850, F-450, F-288, F-128, F-80, F-40, F-20, F-10, F-4, F-2, F-l, A-5000, A-2500, A-1000, and A-500] was used.
• skeleton structure can be obtained by the following method.
• a basic operation is based on JIS K-0070.
• a compound (101) having an azo skeleton structure represented by the structure shown below was manufactured in accordance with the following scheme.
• reaction was performed therebetween for 1 hour at the same temperature as described above (diazonium salt solution) .
• diazonium salt solution To a solution containing 50.0 parts of methanol, 50.0 parts of water, and 17.9 parts of sodium acetate, 6.13 parts of a compound (21) was added and was then iced to 10°C or less. The above diazonium salt solution was dripped to this solution thus prepared and was allowed to react therewith for 2 hours at 10°C or less. After the reaction was
• tert-butyl peroxybenzoate was an organic peroxide
• a compound (141) having an azo skeleton structure represented by the structure shown below was manufactured in accordance with the following scheme.
• a compound (142) having an azo skeleton structure having the structure shown below was manufactured in accordance with the following scheme.
• a prefix a represents a terminal group bonded to the left of the structure.
• W represents a COOH group
• X , Yi , Y 2 , and Z represent the monomer units shown below
• (n) represents a linear alkyl group
• co is a mark
• R 6 i represents a hydrogen atom or an alkyl group.
• R 62 represents a hydrogen atom or an alkyl group
• R 63 represents a carboxylic acid ester group or a carboxylic acid amide group.
• R64 represents a hydrogen atom or an alkyl group
• R6s represents a carboxylic acid ester group or a carboxylic acid amide group.
• R 6 6 represents a hydrogen atom alkyl group.
• a compound in which the "bonding moiety to high molecular portion" is represented by “Z” indicates a compound which forms a linking group by bonding to a COOH group in the monomer unit "Z" in the high molecular portion shown in
• Li to L 8 in Table 2 each represent a linking group and have the following structures.]
• ["*" in the above L x to L 8 represents a bonding position with a carbon atom in the high molecular portion shown in Table 1, and represents a bonding position in the azo skeleton structure shown in Table 2.]
• Yellow pigment dispersions were prepared by the following method.
• Pigment Yellow 185 represented by the following formula (Pig-C), yellow pigment dispersions (Dis-Y43) and (Dis-Y44) were obtained by an operation similar to that in the above preparation example 1 of yellow pigment dispersion.
• Standard yellow pigment dispersions each used as the standard of evaluation and comparative yellow pigment dispersions were prepared by the following methods.
• Magenta pigment dispersions were prepared by the following method.
• Pigment Red 255 represented by the following formula (Pig-F) , magenta pigment dispersions (Dis-M43) and (Dis-M44) were obtained by an operation similar to that in the above preparation example 1 of magenta pigment dispersion.
• Standard magenta pigment dispersions each used as the standard of evaluation and comparative magenta pigment dispersions were prepared by the following methods.
• a standard magenta pigment dispersion (Dis-M47) was obtained by an operation similar to that in the above preparation example 1 of magenta pigment dispersion.
• Cyan pigment dispersions were prepared by the following method.
• cyan pigment dispersions (Dis-C2) to (Dis-C42) were obtained by an operation similar to that in the above preparation example 1 of cyan pigment dispersion.
• Pigment blue 17: 1 represented by the following formula (Pig-I) , cyan pigment dispersions (Dis-C43) and (Dis-C44) were obtained by an operation similar to that in the above preparation example 1 of cyan pigment dispersion.
• dispersions were prepared by the following methods.
• Black pigment dispersions were prepared by the following method.
• black pigment dispersions (Dis-Bk2) to (Dis-Bk42) were obtained by an operation similar to that in the above preparation example 1 of black pigment dispersion.
• dispersions were prepared by the following methods.
• comparative black pigment dispersions (Dis- Bk50) to (Dis-Bk54) were obtained by an operation similar to that in the above preparation example 1 of black pigment dispersion .
• the improvement rate of glossiness is 0% to less than 5%.
• the pigment dispersibility is evaluated as good.
• A The improvement rate of glossiness is 35% or more.
• B The improvement rate of glossiness is 20% to less than 35%.
• the improvement rate of glossiness is 5% to less than 20%.
• the improvement rate of glossiness is less than 5%. When the improvement rate of glossiness is 20% or more, the pigment dispersibility is evaluated as good.
• A The improvement rate of glossiness is 25% or more.
• B The improvement rate of glossiness is 15% to less than 25%.
• the improvement rate of glossiness is 5% to less than 15%.
• the improvement rate of glossiness is less than 5%. When the improvement rate of glossiness is 15% or more, the pigment dispersibility is evaluated as good.
• A The glossiness is 80 more.
• the glossiness is 20 to less than 50.
• composition shown below was heated to 60°C and was uniformly dissolved and dispersed at 5,000 rpm by a high-speed stirring machine, T. K. Homomixer,
• ester wax (maximum endothermic peak by DSC measurement: 70°C, Mn: 704) : 25 parts
• polymer particles were obtained. After the above polymer particles were changed into water and stirred to again form a dispersion liquid, solid-liquid separation was performed by a filter. Re-dispersion of the fine polymer particles in water and solid-liquid separation were repeatedly performed until the compound of phosphoric acid and calcium, which contained Ca 3 (P0 4 ) 2 , was sufficiently removed. Next, fine polymer particles finally obtained by solid-liquid
• Standard yellow toners each used as the standard of evaluation and comparative yellow toners were prepared by the following methods.
• magenta toners were manufactured by the following suspension polymerization method.
• Standard magenta toners each used as the standard of evaluation and comparative magenta toners were prepared by the following methods.
• cyan toners (Tnr-C2) to (Tnr-C42) were obtained by an operation similar to that in the above manufacturing example 1 of cyan toner.
• cyan toners (Tnr-C43) and (Tnr-C44) were obtained by an operation similar to that in the above manufacturing example 1 of cyan toner.
• Standard cyan toners each used as the standard of evaluation and comparative cyan toners were prepared by the following methods.

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