WO2008007776A1 - Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant - Google Patents

Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant Download PDF

Info

Publication number
WO2008007776A1
WO2008007776A1 PCT/JP2007/063997 JP2007063997W WO2008007776A1 WO 2008007776 A1 WO2008007776 A1 WO 2008007776A1 JP 2007063997 W JP2007063997 W JP 2007063997W WO 2008007776 A1 WO2008007776 A1 WO 2008007776A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
acid anhydride
compound
dispersant
polyester
Prior art date
Application number
PCT/JP2007/063997
Other languages
English (en)
Japanese (ja)
Inventor
Tsutomu Hiroshima
Atsushi Nakazato
Joji Mikami
Original Assignee
Toyo Ink Manufacturing Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toyo Ink Manufacturing Co., Ltd. filed Critical Toyo Ink Manufacturing Co., Ltd.
Priority to JP2008524858A priority Critical patent/JP4396777B2/ja
Priority to KR1020097002686A priority patent/KR101354265B1/ko
Priority to CN2007800267222A priority patent/CN101490128B/zh
Publication of WO2008007776A1 publication Critical patent/WO2008007776A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • C09K23/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • 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
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0035—Mixtures of phthalocyanines
    • 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
    • C09B67/006—Preparation of organic pigments
    • C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
    • 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
    • C09B67/006—Preparation of organic pigments
    • C09B67/0069—Non aqueous dispersions of pigments containing only a solvent and a dispersing agent
    • 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
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/10—Treatment with macromolecular organic compounds
    • 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
    • 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
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

Definitions

  • the present invention relates to a polyester dispersant, and more specifically, it is possible to produce a dispersion excellent in non-aggregability, fluidity, and storage stability, which is suitable for fields such as paints and colored resin compositions.
  • the present invention relates to a polyester dispersant, a production method thereof, and a pigment composition using the same.
  • a dispersant is used to maintain a good dispersion state.
  • the dispersant combines the structure of the part that adsorbs to the pigment and the part that has a high affinity for the solvent that is the dispersion medium, and the performance of the dispersant is determined by the balance between these two functional parts.
  • Various dispersants are used according to the surface condition of the pigment to be dispersed.
  • an acidic dispersant is used for a pigment having a surface that is biased toward basicity. In this case, the acidic functional group becomes the adsorption site of the pigment.
  • Dispersants having a carboxylic acid as an acidic functional group are described in, for example, Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, and the like.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 61-61623
  • Patent Document 2 JP-A-1-141968
  • Patent Document 3 JP-A-2-219866
  • Patent Document 4 Japanese Patent Laid-Open No. 11-349842
  • An object of the present invention is to provide a dispersant for obtaining a pigment dispersion which is excellent in dispersibility, fluidity and storage stability at a low use amount. Furthermore, the present invention is suitable for offset inks, gravure inks, color filter resist inks and ink jet inks, paints, colored resin compositions, etc., and has dispersibility and stability excellent in non-aggregation and fluidity. It is an object of the present invention to provide a polyester dispersant.
  • the present invention is produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule.
  • the present invention relates to a polyester dispersant produced by reaction of
  • the present invention is produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule.
  • It also relates to a polyester dispersant produced by reacting.
  • the present invention is produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule,
  • a hydroxyl group in the vinyl polymer (a) having two hydroxyl groups is a hydroxyl group in the vinyl polymer (a) having two hydroxyl groups
  • the present invention relates to a polyester dispersant produced by reaction of
  • the present invention is produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule, A hydroxyl group in the vinyl polymer (a) having two hydroxyl groups, and a hydroxyl group in the polyol compound (c) other than the vinyl polymer (a);
  • the present invention relates to a polyester dispersant produced by reaction of
  • the present invention is produced by reacting a hydroxyl group in a compound (al) having two hydroxyl groups and one thiol group in the molecule with an acid anhydride group in a tetracarboxylic acid anhydride (b).
  • the present invention relates to a polyester dispersant produced by radical polymerization of an ethylenically unsaturated monomer in the presence of the compound (a2).
  • the present invention relates to a compound (al) having two hydroxyl groups and one thiol group in the molecule, and a hydroxyl group and tetracarboxylic acid anhydride in the polyol compound (c ') having no thiol group.
  • the present invention relates to a polyester dispersant produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (a3) produced by reacting with an acid anhydride group in (b).
  • the present invention relates to a hydroxyl group in a compound (al) having two hydroxyl groups and one thiol group in the molecule, an acid anhydride group in a tetracarboxylic acid anhydride (b), and a tricarboxylic acid anhydride (
  • the present invention relates to a polyester dispersant produced by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (a4) produced by reacting with an acid anhydride group in d).
  • the present invention relates to a compound (al) having two hydroxyl groups and one thiol group in the molecule, and a hydroxyl group and tetracarboxylic acid anhydride in the polyol compound (c ') having no thiol group.
  • the compound (a5) produced by reacting the acid anhydride group in (b) with the acid anhydride group in tricarboxylic anhydride (d) the ethylenically unsaturated monomer is radicalized.
  • the present invention relates to a polyester dispersant produced by polymerization.
  • the weight average molecular weight is 2000 to 35000, and the acid value power is 5 to 200.
  • a tetracarboxylic acid anhydride (b) Is represented by the following general formula (1) or general formula (2):
  • the weight average molecular weight of the bulle polymer portion obtained by radical polymerization of an ethylenically unsaturated monomer is 1,000 to 10,000.
  • the glass transition temperature force of the bulle polymer portion obtained by radical polymerization of an ethylenically unsaturated monomer is ⁇ 50 to 70 ° C.
  • the ethylenically unsaturated monomer force benzyl (meth) acrylate is contained in an amount of 20% to 70% by weight based on the whole monomer.
  • an ethylenically unsaturated monomer force includes a monomer represented by the following general formula (3).
  • the present invention relates to a pigment composition containing the above polyester dispersant and a pigment.
  • the present invention relates to a basic derivative selected from the group consisting of a pigment derivative having a basic group, an anthraquinone derivative having a basic group, an attaridone derivative having a basic group, and a triazine derivative having a basic group.
  • the present invention relates to the above pigment composition containing at least one kind.
  • the present invention relates to a pigment dispersion obtained by dispersing the pigment composition in a varnish.
  • the present invention is directed to radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule, so that Step A1 for producing a vinyl polymer (a) having a hydroxyl group,
  • the present invention is directed to radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule, so that Step A2 for producing a vinyl polymer (a) having a hydroxyl group,
  • the present invention is directed to radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule, so that Step A3 for producing a vinyl polymer (a) having a hydroxyl group,
  • the present invention is directed to radical polymerization of an ethylenically unsaturated monomer in the presence of a compound (al) having two hydroxyl groups and one thiol group in the molecule, so that Step A4 for producing a vinyl polymer (a) having a hydroxyl group,
  • a step B4 of reacting the vinyl polymer (a), a tetracarboxylic acid anhydride (b), a polyol compound (c) other than the vinyl polymer (a), and a tricarboxylic acid anhydride (d), and a polyester comprising:
  • the present invention relates to a method for producing a dispersant.
  • the present invention provides a compound by reacting a hydroxyl group in a compound (al) having two hydroxyl groups and one thiol group in the molecule with an acid anhydride group in a tetracarboxylic acid anhydride (b). Step B5 for producing (a2),
  • the present invention relates to a hydroxyl group in a compound (al) having two hydroxyl groups and one thiol group in the molecule and a hydroxyl group in a polyol compound (c ') having no thiol group.
  • the present invention relates to a hydroxyl group in a compound (al) having two hydroxyl groups and one thiol group in the molecule, an acid anhydride group and a tricarboxylic acid anhydride in tetracarboxylic acid anhydride (b). (B) reacting with an acid anhydride group in step B7 to produce compound (a4);
  • the present invention has a hydroxyl group in the compound (al) having two hydroxyl groups and one thiol group in the molecule, an acid anhydride group and a thiol group in the tetracarboxylic acid anhydride (b).
  • the tetracarboxylic acid anhydride (b) is represented by the following general formula (1) or general formula (2):
  • the ethylenically unsaturated monomer contains benzyl (meth) acrylate in an amount of 20% to 70% by weight of the total monomer.
  • the ethylenically unsaturated monomer includes a monomer represented by the following general formula (3):
  • R represents a linear or branched alkyl group having 1 to 4 carbon atoms.
  • polyester dispersant of the present invention it is possible to provide a pigment composition having strong dispersibility, fluidity, and storage stability that has not been obtained conventionally. Furthermore, it is suitable for offset ink, gravure ink, resist ink and ink jet ink for color filters, paints, colored resin compositions, etc., has excellent dispersibility and stability with excellent non-aggregability and fluidity, and high storage stability. And a pigment dispersion having high stability with time.
  • a pigment dispersant has a structure of a part that adsorbs to a pigment and a part that has a high affinity for a solvent as a dispersion medium, and the performance of the dispersant is determined by the balance of these two parts.
  • both the ability of the dispersant to adsorb to the pigment and the affinity to the solvent as the dispersion medium are very important.
  • the tetracarboxylic acid anhydride (b) used in the present invention can react with a hydroxyl group to form an ester bond and leave a pendant carboxyl group on the resulting polyester main chain. Polio-Ruich compound with two hydroxyl groups in one end region (one end region)
  • reaction process formulas of tetracarboxylic anhydride and polyol compound are shown in the following reaction process formulas (4) and (6).
  • n is the number of repeating units.
  • the product of this reaction process will have 2 or 3 carboxyl groups in the X part of the structural formula.
  • the plurality of carboxyl groups are effective as pigment adsorption sites.
  • polyester dispersant of the present invention it is bonded to the core portion X.
  • carboxyl group out of the scope of the present invention
  • the terminal region of A is, for example, a linear or branched trivalent aliphatic hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 8 carbon atoms) (for vinyl polymer portion B). And will be described later).
  • the two hydroxyl groups contained in this one terminal region may be bonded to the same carbon atom or may be bonded to different carbon atoms.
  • a preferable form of the core part X is a reaction residue after reacting with a tetracarboxylic acid anhydride polyolide compound represented by the following general formula (1) or general formula (2).
  • polyester dispersant of the present invention by reacting a vinyl polymer (a) having two hydroxyl groups in one terminal region with a tetracarboxylic acid anhydride (b), the above reaction process formula (4) A plurality of carboxyl group moieties bonded to the core part in the product function as a pigment adsorbing part, and a vinyl polymer part B functions as a solvent affinity part.
  • the compound (al) having two hydroxyl groups and one thiol group is reacted with the tetracarboxylic acid anhydride (b) to contain the vinyl polymer portion B.
  • the compounds (a2) to (a5) are first produced, followed by radical polymerization using the remaining thiol groups of the compounds (a2) to (a5) as chain transfer agents, so that By introducing B, it is possible to obtain a resin having a similar structure.
  • a plurality of carboxyl group moieties bonded to the core portion X in the product are formed in the first steps B5 to B8 to form a pigment adsorbing portion, and then the butyl introduced in the subsequent steps A5 to A8.
  • the polymer part B can function as a solvent affinity part.
  • Step B5 and Step A5 when reacting a compound having two hydroxyl groups and one thiol group (al) with tetracarboxylic anhydride (b) and then introducing an ethylenically unsaturated monomer]:
  • Step B6 and Step A6 [compound having two hydroxyl groups and one thiol group (al), tetracarboxylic anhydride (b) and no thiol group! /, Polyol compound (c,), Subsequently, when ethylenically unsaturated monomer is introduced]:
  • Step B7 and Step A7 [compounds having two hydroxyl groups and one thiol group (al), tetracarboxylic anhydride (b) and tricarboxylic anhydride (d) are reacted, followed by ethylenically unsaturated monoester When introducing a polymer]:
  • Step B8 and Step A8 Compound having two hydroxyl groups and one thiol group (al), tetracarboxylic acid anhydride (b), polyol compound (c ') and tricarboxylic acid anhydride (without thiol group) Reaction with d) followed by introduction of ethylenically unsaturated monomer]: Reaction process formula (10)
  • a plurality of pendant carboxyl groups can be formed to function as a pigment adsorbing portion, and further, radical polymerization can be performed as a chain transfer agent using the remaining thiol groups. It is possible to make the combined part function as a solvent affinity part.
  • the “bule polymer portion formed by radical polymerization of an ethylenically unsaturated monomer” is derived from a tetracarboxylic acid anhydride (b) or a tricarboxylic acid anhydride (d).
  • a plurality of vinyl polymer parts B are usually contained in one molecule constituting the polyester dispersant of the present invention.
  • This part is the affinity part for the solvent that is the dispersion medium.
  • the weight average molecular weight of the vinyl polymer part is less than 1000, the effect of steric repulsion by the solvent affinity part is reduced, and it becomes difficult to prevent the aggregation of the pigment, and the dispersion stability may be insufficient.
  • it exceeds 10000 the absolute amount of the solvent compatible portion increases, and the dispersibility effect itself may decrease. In addition, the viscosity of the dispersion may increase.
  • the vinyl polymer (a) can be easily adjusted in molecular weight to the above range, and has good affinity for the solvent.
  • the glass transition temperature of the bull polymer portion B formed by radical polymerization of an ethylenically unsaturated monomer is preferably 50 to 70 ° C in view of higher dispersibility of the pigment. 50 ⁇ 40 ° C is more preferred.
  • Tg glass transition temperature
  • a skeleton derived from a compound having two hydroxyl groups and one thiol group in the molecule is also present in the vinyl polymer (a), but is excluded from the following calculation for calculating the glass transition temperature.
  • Tg is the glass transition temperature of the entire Bule polymer part B
  • W1 to Wn are the weight fractions of the monomers used
  • Tgl to Tgn are the glass weights of each homopolymer.
  • the Tg of the main homopolymer used for calculation is shown below.
  • Methyl metatalylate 105 ° C (378K)
  • the glass of the buule polymer portion obtained by radical polymerization of an ethylenically unsaturated monomer synthesized using 100 parts of n-butyl methacrylate and 100 parts of benzyl methacrylate.
  • the transition temperature is 36.1 ° C.
  • a vinyl polymer having two hydroxyl groups in one terminal region is obtained by laminating an ethylenically unsaturated monomer in the presence of a compound having two hydroxyl groups and one thiol group in the molecule of the present invention.
  • the following method can also be used.
  • the method power S for radical polymerization of ethylenically unsaturated monomers in the presence of a compound having two hydroxyl groups and one thiol group is most preferable.
  • a vinyl polymer (a) having two hydroxyl groups at one end region is obtained by radical polymerization of an ethylenically unsaturated monomer in the presence of a compound having two hydroxyl groups and one thiol group in the molecule. Can be obtained at
  • Examples of compounds having two hydroxyl groups and one thiol group in the molecule include 1 mercapto 1,1 methanediol, 1 mercapto 1,1 ethanediol, 3 mercapto 1,2-propanediol (thiol).
  • a compound having two hydroxyl groups and one thiol group in the molecule can be obtained by mixing and heating.
  • the compound having two hydroxyl groups and one thiol group is based on 100 parts by weight of ethylenically unsaturated monomer. It is preferable to perform bulk polymerization or solution polymerization using 1 to 30 parts by weight, more preferably 3 to 12 parts by weight, still more preferably 4 to 12 parts by weight, and particularly preferably 5 to 9 parts by weight.
  • the reaction temperature is 40 to 150 ° C, preferably 50 to 110 ° C.
  • a polymerization initiator in the polymerization, 0.005 to 5 parts by weight of a polymerization initiator can be arbitrarily used with respect to 100 parts by weight of the ethylenically unsaturated monomer.
  • a polymerization initiator azo compounds and organic peroxides can be used.
  • azo compounds examples include 2,2'-azobisisobutyryl-tolyl, 2,2, -azobis (2-methylbutybutoxy-tolyl), 1,1, -azobis (cyclohexane 1-carbo-tolyl) ), 2, 2, -azobis (2,4 dimethylvale-tolyl), 2, 2, monoazobis (2,4 dimethyl-4-methoxyvaleronitryl), dimethyl 2,2'-azobis (2 methylpropio) Nate), 4, 4, azobis (4 cyanoberic acid), 2, 2, azobis (2-hydroxymethylpropio-tolyl), 2, 2, azobis [2- (2-imidazoline-2-yl) Propane] and the like.
  • organic peroxides examples include benzoyl peroxide, t-butyl perbenzoate, tamen hydroperoxide, diisopropyl peroxydicarbonate, di-propinoliver oxydicarbonate, di (2-ethoxyethyl) per Examples include oxydicarbonate, t-butyl peroxyneodecanoate, t-butyl peroxybivalate, (3,5,5-trimethylhexanoyl) peroxide, dipropio-peroxide, dicetylba 1-year-old oxide. These polymerization initiators can be used alone or in combination of two or more.
  • a polymerization solvent ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, methyl ethyl ketone, cyclohexanone, etc. are used. It is not limited. These polymerization solvents may be used as a mixture of two or more.
  • Examples of the ethylenically unsaturated monomer include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl ( (Meth) Atalylate, Isobutyl (Meth) Atalylate, t-Butyl (Meth) Atalylate, 2—Ethylhexyl (Meth) Atalylate, Cyclohexyl (Meth) Atalylate, Stearyl (Meth) Atalylate, Lauryl ( (Meth) Atarylate, Tetrahydrofurfuryl (Meth) Atarylate, Isobol (Meth) Atarylate, Phenol (Meth) Atarylate, Benzyl (Meth) Atrelyle , Oxetane (meth) acrylate, etc., methoxypolypropylene glycol (meth) acryl
  • Examples of monomers that can be used in combination with the above acrylic monomers include styrenes such as styrene and a-methylstyrene, vinyl ethers such as ethyl vinyl ether, n -propyl vinyl ether, isopropyl vinyl ether, n -butyl vinyl ether, and isobutyl vinyl ether. And fatty acid burs such as vinyl acetate and vinyl propionate.
  • a carboxyl group-containing ethylenically unsaturated monomer may be used in combination.
  • the carboxyl group-containing ethylenically unsaturated monomer one or more kinds can be selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid and the like.
  • benzyl (meth) acrylate is used in an amount of 20 to 70% by weight based on the whole monomer. It is preferably 30 to 60% by weight. If it is less than 20% by weight, the solvent affinity becomes low, and sufficient steric repulsion effect cannot be obtained, and the pigment dispersibility may decrease. If it exceeds 70% by weight, the benzyl part and the pigment interact with each other. As a result, the pigment dispersibility may decrease.
  • a monomer represented by the following general formula (3) is preferably 20 to 70% by weight, more preferably 20 to 100% by weight, based on the whole monomer.
  • the solvent affinity is improved and the pigment dispersibility is improved.
  • R represents a linear or branched alkyl group having 1 to 4 carbon atoms.
  • the polyester dispersant of the present invention comprises a hydroxyl group of a vinyl polymer (a) having two hydroxyl groups in one end region obtained in steps A1 to A4, and an acid anhydride group of a tetracarboxylic acid anhydride (b). It is obtained by reacting (Steps Bl to B4).
  • the tetracarboxylic acid anhydride (b) used in the present invention includes 1, 2, 3, 4 butanetetracarboxylic acid anhydride, 1, 2, 3, 4 cyclobutanetetracarboxylic acid anhydride, 1, 3 Dimethyl 1,2,3,4-cyclobutanetetracarboxylic anhydride, 1,2,3,4-cyclopentane tetracarboxylic anhydride, 2,3,5 tricarboxycyclopentylacetic anhydride, 3,5,6 tricarboxy Norbornane-2-acetic anhydride, 2, 3, 4, 5-tetrahydrofuran tetracarboxylic anhydride, 5- (2,5 dioxotetrahydrofural) -3-methyl-3-cyclohexene 1,2-dicarboxylic anhydride , Bicyclo [2, 2, 2] -Otato 7-en 2, 2, 5, 5, 6-tetracarboxylic anhydride and other aliphatic tetracarbox
  • the tetracarboxylic acid anhydride used in the present invention is not limited to the compound exemplified above, and any structure having two forceful rubonic acid anhydride groups can be used! Powerful! These can be used alone or in combination.
  • what is preferably used in the present invention is an aromatic tetracarboxylic acid anhydride from the viewpoint of reducing the viscosity of the pigment dispersion, more preferably a tetracarboxylic acid anhydride having two or more aromatic rings. is there.
  • a compound having one carboxylic anhydride group in the molecule or a compound having three or more can be used in combination.
  • tricarboxylic acid anhydrides include aliphatic tricarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides.
  • Examples of the aliphatic tricarboxylic acid anhydride include, for example, 3 carboxymethyldaltaric acid anhydrous, 1, 2, 4 butanetricarboxylic acid 1, 2 anhydride, cis propene-1, 2, 3 tricarboxylic acid 1 , 2 anhydride, 1,3,4-cyclopentanetricarboxylic acid anhydride and the like.
  • aromatic tricarboxylic acid for example, benzenetricarboxylic acid anhydride (1, 2, 3-benzenetricarboxylic acid anhydride, trimellitic acid anhydride [1, 2, 4 benzenetricarboxylic acid anhydride], etc.), Naphthalene tricarboxylic acid anhydride (1, 2, 4 naphthalene tricarboxylic acid anhydride, 1, 4, 5 naphthalene tricarboxylic acid anhydride, 2, 3, 6 naphthalene tricarboxylic acid anhydride, 1, 2, 8 naphthalene tricarboxylic acid anhydride 3, 4, 4 'monobenzophenone tricarboxylic acid anhydride, 3, 4, 4, biphenyl ether tricarboxylic acid anhydride, 3, 4, 4, biphenyl tricarboxylic acid anhydride, 2, 3 1, 2, -biphenyl tricarboxylic acid anhydride, 3, 4, 4, 4, 4, 4, 4, 4, 4,
  • a polyol compound (c) other than the vinyl polymer (a) in an arbitrary ratio in the step B2 and the step B4.
  • a polyol compound (c) other than the vinyl polymer (a) it becomes easy to adjust the density of the carboxylic acid group and the proportion of the solvent-soluble portion.
  • polyol compound (c) other than the vinyl polymer (a) used in the present invention, a known one can be used. For example, it has 2 to 4 hydroxyl groups in one molecule. Polio-Iloui compound can be used. Among them, there are those belonging to the following groups (1) to (7) if only typical ones are illustrated.
  • Polyester polyols obtained by co-condensation of one or more of the above-mentioned various polyhydric alcohols with polyvalent carboxylic acids which are polyvalent carboxylic acids such as succinic acid, adipic acid, sebacin Acid, azelaic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, fumaric acid, citraconic acid, itaconic acid, glutaconic acid, 1, 2, 5 monohexanetricarboxylic acid, 1,4-cyclohexanehical
  • boric acid 1, 2, 4 benzene tricarboxylic acid, 1, 2, 5 benzene tricarboxylic acid, 1, 2, 4 cyclohexatricarboxylic acid or 2, 5, 7 naphthalene tricarboxylic acid Resulting polyols;
  • polyester polyols obtained by polycondensation reaction of the various polyhydric alcohols, polycarboxylic acids and various latatones;
  • examples thereof include silicon resin.
  • the polyol compound (c) other than the vinyl polymer (a) optionally added as shown in (1) to (7) may be used alone or in combination of two or more.
  • the weight average molecular weight is 40 to: LOOOO force S, preferably 100 to 2000, and more preferably 100 to 1000.
  • the catalyst used for the production of the polyester dispersant of the present invention a known catalyst can be used.
  • the catalyst is preferably a tertiary amine compound such as triethylamine, triethylenediamine, N, N-dimethylbenzylamine, N-methylmorpholine, 1,8-diazabicyclo [5.4.0] — 7-undecene, 1,5-diazabicyclo [4.3.0] 1-5-nonene, and the like.
  • the polyester dispersant of the present invention can be produced using only the raw materials listed above, but it is preferable to use a solvent that avoids problems such as high viscosity and non-uniform reaction. preferable.
  • a solvent that avoids problems such as high viscosity and non-uniform reaction.
  • known solvents can be used. Examples include acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl acetate, butylacetate, toluene, xylene, and acetonitrile.
  • the solvent used for the reaction can be removed by distillation or other operation after the completion of the reaction, or used as part of the product.
  • the polyester dispersant of the present invention comprises a vinyl polymer (a) having two hydroxyl groups in one terminal region, a tetracarboxylic acid anhydride (b), and an optional addition "other than the vinyl polymer (a). It is obtained by reacting the polyol compound (c) ”.
  • the remaining acid anhydride group may be hydrolyzed with a necessary amount of water and used. If it is less than 0.3, the acid anhydride residue as the pigment adsorbing portion may be decreased, and the acid value of the resin may be decreased. On the other hand, if it exceeds 1.2, acid anhydride groups remain in the polyester, which may cause problems in storage stability of the resin. In addition, the amount of water necessary to hydrolyze the remaining acid anhydride groups may increase, resulting in poor solvent solubility.
  • the polyester dispersant of the present invention is a polyol polymer other than (a), a vinyl polymer (a) having two hydroxyl groups in one terminal region, a tetracarboxylic acid anhydride (b), and an optional addition (a). It can be obtained by reacting compound (c) and tricarboxylic anhydride (d).
  • the reaction temperature is 50 ° C to 180 ° C, preferably 80 ° C to 140 ° C.
  • the reaction rate is slow.
  • the reaction temperature is 180 ° C or higher, the carboxyl group undergoes esterification reaction, which may cause a decrease in acid value or gelling. It is ideal to stop the reaction until there is no absorption of the acid anhydride by infrared absorption. After confirming that 95% or more of the acid anhydride is half-esterified by acid value measurement Stop the reaction.
  • the weight average molecular weight of the obtained polyester dispersant is preferably 2000 to 35000, more preferably ⁇ or 4000 to 25000, more preferably ⁇ or 6000 to 20000, particularly preferably ⁇ ⁇ is between 7000 and 15000. If the weight average molecular weight is less than 2000, the stability of the pigment composition may decrease. Thickening may occur.
  • the acid value of the obtained polyester dispersant is preferably 5 to 200. More preferably, it is 10-150, More preferably, it is 15-: LOO, Especially preferably, it is 20-80. When the acid value is less than 5, the pigment adsorbing ability may be lowered and the pigment dispersibility may be problematic. When the acid value exceeds 200, the interaction between the rosils may be increased and the viscosity of the pigment dispersion composition may be increased. .
  • a compound (al) having two hydroxyl groups and one thiol group in the molecule a tetracarboxylic acid anhydride (b), a polyol compound (c ′) having no thiol group, and Steps B5 to B8 for producing compound (a2) by reacting with tricarboxylic acid anhydride (d), and thiol group of compound (a2) remaining in the presence of compound (a2)!
  • a dispersant having the same structure can be obtained by the steps A5 to A8 in which radical polymerization is performed as a chain transfer agent.
  • a compound having two hydroxyl groups and one thiol group in the molecule (al), a tetracarboxylic acid anhydride (b), and optionally a polyurich compound (c ') having no thiol group
  • Steps B5 to B8 in which compounds (a2) to (a5) are produced by further reacting with a tricarboxylic acid anhydride (d) in some cases will be described.
  • These compounds (a2) to (a5) are compounds other than the compound (al) having two hydroxyl groups and one thiol group in the molecule (al), tetracarboxylic acid anhydride (b), and optionally added (a).
  • the polyol compound (c) and the optionally added tricarboxylic acid anhydride (d) can be obtained in the same manner as in Steps A1 to A4. It has an acid anhydride group in tetracarboxylic acid anhydride (b) and triforce rubonic acid anhydride (d), a compound having two hydroxyl groups and one thiol group in the molecule (al), and a thiol group.
  • LOO parts by weight of an ethylenically unsaturated monomer is used. It is preferable to perform bulk polymerization or solution polymerization. More preferably, it is 8-25 weight part, More preferably, it is 10-20 weight part.
  • the reaction temperature is 40 to 150 ° C, preferably 50 to 110 ° C.
  • the ethylenically unsaturated monomer having a hydroxyl group used in the above production method may be any monomer having a hydroxyl group and having an ethylenically unsaturated double bond.
  • (meth) acrylate monomers having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate, 2 (or 3) -hydroxypropyl (meth) acrylate, 2 (Or 3 or 4) -hydroxybutyl (meth) acrylate and hydroxyalkyl (meth) acrylate, such as cyclohexane dimethanol mono (meth) acrylate, or
  • (meth) acrylamide monomers having a hydroxyl group such as N- (2-hydroxyethyl) (meth) acrylamide, N- (2-hydroxypropyl) (meth) acrylamide, N- (2-hydroxybutyl) (meth) ) N- (hydroxyalkyl) (meth) acrylamide such as
  • the ethylenically unsaturated monomer obtained can also be used as the ethylenically unsaturated monomer (h) having a hydroxyl group in the production method used in the present invention.
  • the alkylene oxide to be added ethylene oxide, propylene oxide, 1, 2 1, 4 2, 3-— or 1,3-butylene oxide and a combination system of two or more of these are used.
  • the bond type may be random and either Z or block.
  • the added ratataton include ⁇ -noratolatataton, ⁇ -force prolatatatone, ⁇ -one-proteatone substituted with an alkyl group having 16 carbon atoms, and a combination of two or more of these.
  • An alkylene oxide and a rataton may be added.
  • pigments that can be dispersed with the dispersant of the present invention include various pigments used in inks and the like.
  • Such pigments include soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, perylene pigments, perinone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinone pigments, anthracirimide pigments.
  • titanium dioxide, iron oxide, metal oxides such as antimony pentoxide, zinc oxide, silica, cadmium sulfate, calcium carbonate, barium carbonate, barium sulfate, clay, talc, chrome, Inorganic pigments such as carbon black can also be used. Carbon black Any carbon black such as neutral, acidic, and basic can be used.
  • the pigment composition of the present invention is not limited to the above-described pigment, and for example, solid fine particles containing metal fine particles such as gold, silver, copper, platinum, iron, cobalt, nickel, and Z or alloys thereof can be used. .
  • the pigment composition using the dispersant of the present invention further has a pigment derivative having a basic group, an anthraquinone derivative having a basic group, an attaridone derivative having a basic group, and a basic group.
  • Group power of triazine derivatives It is preferable to include at least one basic derivative selected.
  • the pigment derivative is a product obtained by introducing a specific substituent into the organic pigment residue described in the color index.
  • a pigment derivative having a basic group is used.
  • the basic derivative that can be used in the pigment composition of the present invention has a pigment derivative having a basic group, an anthraquinone derivative having a basic group, an attaridone derivative having a basic group, and a basic group. It is selected from the group of triazine derivatives.
  • the basic group of the basic derivative that can be used in the pigment composition of the present invention is a group force having a basic force represented by the following general formulas (6), (7), (8), and (9). At least one group selected.
  • x and xx 2 are SO CO—, CH NHCOCH-CH one or direct bond
  • n an integer of 1 to 10.
  • R 2 each independently represents an optionally substituted alkyl group, alkenyl group, phenyl group, or a heterocyclic ring formed by combining R 1 and R 2 .
  • the heterocycle may contain further nitrogen, oxygen or sulfur atoms.
  • the alkyl group and alkenyl group preferably have 1 to 10 carbon atoms.
  • R 3 represents an alkyl group, a alkenyl group or a phenyl group which may be substituted.
  • Alkyl and alkenyl groups preferably have 1 to 10 carbon atoms! /.
  • R 4 , R 5 , R 6 , and R 7 each independently represents a hydrogen atom, an alkyl group, a alkenyl group, or a fuller group that may be substituted. As for carbon number of an alkyl group and an alkenyl group, 1-5 are preferable.
  • Y represents NR 8 —Z—NR 9 or a direct bond.
  • R 8 and R 9 each independently represents a hydrogen atom, an optionally substituted alkyl group, an alcohol group, or a phenol group.
  • the alkyl group and the alkyl group preferably have 1 to 5 carbon atoms.
  • Z represents an optionally substituted alkylene group, alkylene group, or fullerene group.
  • Alkyl and alkenyl groups preferably have 1 to 8 carbon atoms! /.
  • P represents a substituent represented by the formula (10) or a substituent represented by the formula (11).
  • Q represents a hydroxyl group, an alkoxyl group, a substituent represented by the formula (10) or a substituent represented by the formula (11).
  • alkyl group in I ⁇ to R 9 in the general formula a methyl group, Echiru group, propyl group, butyl group, pentyl group, etc. hexyl group to.
  • alkenyl group include a vinyl group and a probe group.
  • Examples of the alkylene group for Z in the above general formula include a methylene group, an ethylene group, a propylene group, and a butylene group.
  • Examples of the alkellene group include a vinylene group and a p-bene group.
  • Examples of the alkoxyl group for Q in the above general formula include a methoxy group, an ethoxy group, a alkoxy group, and a butoxy group.
  • Examples of the functional group which may be substituted include a halogen group, a cyano group, an alkoxyl group, an amino group, a hydroxyl group, a nitro group, and an epoxy group.
  • Examples of the amine component used to form the substituents represented by the formulas (6) to (9) include dimethylamine, jetylamine, N, N-ethylisopropylamine, N, N- Tylpropylamine, N, N-methylbutyramine, N, N-methylisobutyramine, N, N butylethylamine, N, N-tert butylethylamine, diisopropylamine, dipropylamine, N, N-sec butylpropylamine, dibutylamine, disec-butylamine, diisobutylamine, N, N isobutyl-sec butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N—Methyloctadecylamine, didecylamine, diarylamine, N, N ethyl-1,
  • the organic dye constituting the pigment derivative having a basic group includes, for example, diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, polyazo, phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine , Flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone and other anthraquinone dyes, quinacridone dyes, dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindoline dyes, isoindolinone dyes , Quinophthalone dyes, selenium dyes, metal complex dyes, and the like.
  • diketopyrrolopyrrole dyes such as azo, disazo, polyazo, phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine , Flavantron, anthanthrone
  • an anthraquinone derivative having a basic group and an attaridone derivative having a basic group are alkyl groups such as a methyl group and an ethyl group, an amino group, a nitro group, a hydroxyl group, or an alkoxy group such as a methoxy group and an ethoxy group.
  • substituents such as halogens, such as chlorine.
  • triazines constituting triazine derivatives having a basic group include alkyl groups (methyl group, ethyl group, butyl group, etc.), amino groups, alkylamino groups (dimethylamino group, jetramino group, dibutylamino group, etc.) ), Nitro group, hydroxyl group, alkoxy group (methoxy group, ethoxy group, butoxy group, etc.), halogen (chlorine, bromine, etc.), phenyl group (alkyl group, amino group, alkylamino group, nitro group, hydroxyl group, alkoxy group) And may be substituted with a halogen, etc.), and a phenylamino group (which may be substituted with an alkyl group, amino group, alkylamino group, nitro group, hydroxyl group, alkoxy group, halogen, etc.), etc. It is 1, 3, 5 triazine which may have the following substituents.
  • the pigment derivative, anthraquinone derivative and attaridone derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, after introducing a substituent represented by the general formulas (12) to (15) into an organic dye, anthraquinone or attaridone, it reacts with the above-described substituents to obtain a substituent represented by the general formulas (6) to (9).
  • Group-forming amine components such as N, N-dimethylaminopropylamine, N-methylbiperazine, jetylamine or 4 [4 hydroxy-6- [3- (dibutylamino) propylamino]] 1, 3, 5 triazine-2 It can be obtained by reacting —ylamino] -lin or the like.
  • the organic dye is a azo dye
  • the substituents represented by the general formulas (6) to (9) are introduced into the diazo component or the coupling component, and then the coupling reaction is performed. It is also possible to produce an azo pigment derivative.
  • the triazine derivative having a basic group can be synthesized by various synthetic routes.
  • an amine component starting from cyanuric chloride and forming a substituent represented by formula (6) to formula (9) on at least one chlorine of the salt cyanuric, such as N, N-dimethylaminopropylamine or It can be obtained by reacting N-methylbiperazine or the like and then reacting the remaining chlorine of the cyanuric chloride with various amines or alcohols.
  • the amount of the basic derivative is preferably 1 to 50 parts by weight, more preferably 3 to 30 parts by weight, most preferably 100 parts by weight of the pigment. 5 to 25 parts by weight.
  • the blending amount of the polyester dispersant is preferably 1 to 200 parts by weight, more preferably 2 to 175 parts by weight, and most preferably 5 to 150 parts by weight with respect to 100 parts by weight of the pigment.
  • the pigment composition using the polyester dispersant of the present invention may be mixed with various solvents, resin, additives, etc. as necessary to obtain a horizontal sand mill, a vertical sand mill, a Yura-la type bead mill, an attritor, etc.
  • the pigment dispersion obtained by dispersing the pigment composition in the varnish can be prepared.
  • all components may be mixed to disperse the force, but initially only the pigment and the basic derivative, or the basic derivative Only with polyester dispersant or face It is also possible to disperse the material, the basic derivative, and the polyester dispersant alone, and then add another component to perform dispersion again.
  • a kneader mixer such as an adader, 3-roll mill, etc.
  • any dispersing machine or mixer such as a speed mixer, a homomixer, a ball mill, a roll mill, a stone mill, or an ultrasonic dispersing machine can be used to produce the pigment dispersion.
  • Examples of various solvents that can be used in the pigment dispersion include organic solvents and water.
  • an active energy ray-curable liquid monomer or liquid oligomer may be used as a medium instead of a solvent.
  • Examples of the resin that can be used in the pigment dispersion of the present invention include petroleum resin, power zein, shellac, rosin-modified maleic acid resin, rosin-modified phenol resin, nitrocellulose, cellulose acetate.
  • polyester dispersant of the present invention can be used as a binder resin for a pigment dispersion.
  • the pigment dispersion of the present invention is used for non-aqueous, aqueous or solvent-free paints, gravure ink, offset ink, ink jet ink, color filter ink, digital paper ink, plastic coloring, etc. it can.
  • a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 200 parts of n-butyl methacrylate and replaced with nitrogen gas.
  • the inside of the reaction vessel was heated to 80 ° C., and 12 parts of 3-mercapto 1,2-propanediol was added to react for 12 hours. Solid content measurement confirmed that 95% had reacted.
  • 12 parts of pyromellitic anhydride, 224 parts of cyclohexanone and 1,8 diazabicyclo [5.4.0] —7 undecene 0.40 parts as catalyst were added and reacted at 120 ° C for 7 hours. I let you.
  • a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 100 parts of n-butyl methacrylate and 100 parts of benzyl methacrylate and replaced with nitrogen gas.
  • the reaction vessel was heated to 80 ° C, and a solution of 0.1 part of 2,2'-azobisisobutyl-tolyl was added to 12-liter of 3-menorecapto 1,2 pronogen, Reacted for hours. It was confirmed that 95% had reacted by solid content measurement.
  • n-butyl methacrylate 100 parts of relate and 100 parts of benzylmetatalylate were charged and replaced with nitrogen gas.
  • the reaction vessel was heated to 80 ° C, and a solution of 0.1 part of 2,2'-azobisisobutyl-tolyl was added to 12-liter of 3-menorecapto 1,2 pronogen, Reacted for hours. It was confirmed that 95% had reacted by solid content measurement.
  • 37 parts of BPDA, 255 parts of cyclohexanone, and 1.40 diazabicyclo- [5.4.0] -7.40 parts as a catalyst were added and reacted at 120 ° C for 7 hours.
  • a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 100 parts of n-butyl methacrylate and 100 parts of n-butyl acrylate and replaced with nitrogen gas.
  • the reaction vessel was heated to 80 ° C, and a solution of 0.1 part of 2,2'-azobisisobutyl-tolyl was added to 12-liter of 3-menorecapto 1,2 pronogen, Reacted for hours. It was confirmed that 95% had reacted by solid content measurement. 4 parts of PMA, 26 parts of trimellitic anhydride, 242 parts of cyclohexanone, 1,8 diazabicyclo [5. 4. 0] — 7 undenecene as catalyst.
  • Example 29 and 30 Synthesis was carried out in the same manner as in Example 28 except that the raw materials and preparation amounts shown in Table 1 were used, and a polyester dispersant was obtained.
  • a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 100 parts of n-butyl methacrylate and 100 parts of n-butyl acrylate and replaced with nitrogen gas.
  • the reaction vessel was heated to 80 ° C, and a solution of 0.1 part of 2,2'-azobisisobutyl-tolyl was added to 12-liter of 3-menorecapto 1,2 pronogen, Reacted for hours. It was confirmed that 95% had reacted by solid content measurement.
  • a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 12 parts of 3-mercapto-1,2-propanediol, 19 parts of PMA, and 31 parts of cyclohexanone and replaced with nitrogen gas.
  • the reaction vessel was heated to 100 ° C and reacted for 7 hours. After measuring the acid value to confirm that 98% or more of the acid anhydride was half-esterified, the temperature in the system was cooled to 70 ° C, and 100 parts of n-butyl metatalylate and benzyl metataliate were cooled.
  • a reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer was charged with 12 parts of 3-mercapto-1,2-propanediol, 37 parts of PMA, 11 parts of neopentyl glycol, and 60 parts of cyclohexanone. Replaced.
  • the inside of the reaction vessel was heated to 100 ° C and reacted for 7 hours.
  • the acid value was measured to confirm that 98% or more of the acid anhydride had been half-esterified, and then the temperature inside the system was cooled to 70 ° C., and 80 parts of methyl metatalylate and 80 parts of butyl acrylate.
  • a reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer was charged with 12 parts of 3-mercapto-1,2-propanediol, 12 parts of PMA, 11 parts of trimellitic anhydride, and 35 parts of cyclohexanone. Replaced with nitrogen gas. The inside of the reaction vessel was heated to 100 ° C and reacted for 7 hours.
  • the temperature inside the system was cooled to 70 ° C., and 80 parts of methyl metatalylate and butyl acrylate 80 Part, 20 parts of hydroxyethinoremethalate, 20 parts of 2-hydroxypropenoremethalate, 200 parts of cyclohexanone solution containing 0.5 part of 2,2'-azobisisobutyric-tolyl added. And reacted for 10 hours.
  • the solid content measurement confirmed that the polymerization had progressed 95%, and the reaction was completed.
  • a polyester dispersant having an acid value of 53 and a weight average molecular weight of 10,000 was obtained.
  • Example 47 In a reaction vessel equipped with a gas inlet tube, thermometer, condenser, and stirrer, 3-mercapto-1,2-propanediol 12 parts, PMA 15 parts, neopentyl glycol 11 parts, trimellitic anhydride 14 parts, cyclohexanone 52 parts were charged and replaced with nitrogen gas. The reaction vessel was heated to 100 ° C and reacted for 7 hours. After the acid value measurement confirmed that 98% or more of the acid anhydride had been condensed, the temperature inside the system was cooled to 70 ° C., and 80 parts of methyl methacrylate and 100 parts of butinorea tallylate were added.
  • Dispersant 9 n-Butyl methacrylate 200 100 100 90 100 100 100 100 100 100 Benzyl methacrylate 100 100 100 100 100 100 100 100 100 100 100 100 Lauryl methacrylate
  • Methyl methacrylate 140 unsaturated monomer
  • Solvents Open mouth hexanone 232 232 266 220 261 356 294 462 Glass transition temperature of vinyl polymer part (t) 36 36 6 14 14 1 36 17 Acid number 42 43 77 29 73 54 49 41 w 9100 11000 8200 18500 13000 22000 15000 23000 6]
  • butyl methacrylate 90 Benzyl methacrylate 100 100 Lauryl methacrylate
  • PMA pyromellitic anhydride (manufactured by Daicel Engineering Co., Ltd.)
  • BPDA 3, 3 ', 4, 4'-biphenyltetracarboxylic acid anhydride (Mitsubishi Chemical Co., Ltd.)
  • BPAF 9, 9 Bis (3, 4-dicarboxyphenol) fluorene dianhydride (Manufactured by JFE Chemical)
  • DMBA dimethylol butanoic acid (manufactured by Perstorp)
  • a four-necked flask equipped with a stirrer, reflux condenser, gas inlet tube, thermometer, and dropping funnel was 19.8 parts of silene, 2.1 parts of octanol, 1 part of prolatatone epsilon 77.9 parts of tetrabutyl titanate 0.16 parts, heated to 150-160 ° C and reacted for 5 hours under nitrogen gas atmosphere After confirming that the caro heat residue was 78% or more, it was cooled to obtain a polyester monool. 31.86 parts of the synthesized polyester monool and 0.98 parts of trimellitic anhydride were charged and reacted at 150 to 160 ° C. in a nitrogen atmosphere.
  • YED122 (trade name: alkylphenol monoglycidyl ether, epoxy equivalent 250, manufactured by Japan Epoxy Resin Co., Ltd.), 2. 55 parts when succinic acid value becomes 22.7 or less, react at the same temperature It was.
  • succinic acid value is 1.1 or less, add 1.96 parts of trimellitic anhydride and react at the same temperature.
  • YED122 5 Charge 1 part and react at the same temperature.
  • succinic acid number drops to 1.8 or less, add 3.92 parts trimellitic anhydride and react at the same temperature.
  • the temperature became 60.1 or less the mixture was cooled and 53.6 parts of xylene was added to terminate the reaction.
  • a polyester dispersant having an acid value of 58.9 and a weight average molecular weight of 11 000 was obtained.
  • the polyester dispersant prepared in Comparative Example 4 corresponds to the polyester dispersant described in Patent Document 3.
  • polyester dispersant prepared in Comparative Example 5 corresponds to the polyester dispersant described in Patent Document 4.
  • CuPc represents a copper phthalocyanine residue.
  • CuPc represents a copper phthalocyanine residue.
  • a pigment derivative (Y4) having a basic group was obtained in the same manner as in Production Example 1 using diphenyl diketopyrrolopyrrole as the dye component and N-aminopropylmorpholine as the amine component.
  • the following pigment derivatives, anthraquinone derivatives, attaridone derivatives or triazine derivatives were obtained by the same method as in Production Examples 1 to 4 of the pigment derivative (Y) having the basic group.
  • the pigment As shown in Table 7, the pigment (CI Pigment Blue 15: 3), the polyester dispersant synthesized in Examples 1 to 9, the pigment derivative (Y1) having a basic group synthesized in Production Example 1, and A pigment composition was prepared by blending cyclohexanone and dispersing 100 parts of 2 mm diameter Zirco Your beads in a paint paint conditioner for 3 hours.
  • a pigment composition was prepared in the same manner as in Examples 51 to 59 except that the carboxyl group-containing polyester synthesized in Comparative Examples 1 and 2 was used.
  • the viscosity of the obtained composition was measured with a B-type viscometer (25 ° C, rotation speed lOOrpm), and the haze was measured with a haze meter (light transmittance 20%).
  • the performance of the dispersion was evaluated based on the initial viscosity and haze (the lower the viscosity, the better the haze, the lower the haze, the better).
  • Initial viscosity and haze are measured after standing at room temperature for 1 day after dispersion. The temperature was measured after leaving at 40 ° C for one week. The results are shown in Table 7.
  • the pigment compositions of Examples 51 to 59 using the polyester dispersant of the present invention have a low initial viscosity and are almost free from an increase in viscosity over time. It shows stability. Furthermore, the haze is also low.
  • the pigment compositions of Comparative Examples 6 and 7 were found to have problems with high dispersibility in both viscosity and haze.
  • Pigment Blue 15 9 parts as pigment, 1 part of pigment derivative (Y1) with basic group, 1 part of dispersant 3 (solid), alkyd resin (Talkid 133-60 from Hitachi Chemical Co., Ltd.) 29 parts and 60 parts of cyclohexanone were charged into a mayonnaise bottle, 250 parts of 0.5 mm diameter Zircoyu beads were charged as a dispersion medium, and this dispersion was performed with a paint shaker to obtain a facial dispersion.
  • the viscosity of the obtained pigment dispersion was measured with a B-type viscometer, and the performance of the dispersion was evaluated by viscosity and TI value (viscosity at 6 rpm, viscosity at Z60 rpm).
  • the viscosity at 6 rpm was 1 lOmPa ⁇ s
  • the viscosity at 60 rpm was lOOmPa's
  • the TI value was 1.11.
  • the obtained pigment dispersion was stored in a thermostat at 50 ° C. for 1 week and accelerated with time, and the change in viscosity of the pigment dispersion before and after aging was measured.
  • the viscosity at 6 rpm was 105 mPa's and the rate of change was 5%. After the pigment dispersion was coated on glass and the solvent was removed, the weight loss% before and after heating at 200 ° C for 1 hour was 8.5%.
  • Example 60 In the same manner as in Example 60, the pigments were mixed at the blending ratios (weight ratios) shown in Tables 8 and 9, respectively. A dispersion was obtained. The evaluation was made in the same manner as in Example 60 (the lower the viscosity, the better, the closer the TI value is to 1, the better).
  • Viscosity stability is ⁇ or 10 if the rate of change in viscosity before and after storage at 50 ° C for 1 week is within ⁇ 10%.
  • the coating weight loss is 200 ° C after removing the coating film and solvent on the glass.
  • Example 60 Pigment Blue 15: 3 9 Yl 1 Dispersant 3 1 29 60
  • Example 61 Pigment Blue 15: 3 9 Yl 1 Dispersant 7 1.5 28.5 60
  • Example 62 Pigment Blue 15: 3 9 Yl 1 Dispersant 8 1 29 60
  • Example 63 Pigment Blue 15: 3 9 Yl 1 Dispersant 10 1 29 60
  • Example 64 Pigment Blue 15: 3 9 Yl 1 Dispersant 13 1 29 60
  • Example 65 Pigment Blue 15: 3 9 Yl 1 Dispersant 14 1 29 60
  • Example 66 Pigment Blue 15: 3 9 Yl 1 Dispersant 15 1 29 60
  • Example 67 Pigment Blue 15: 3 9 Yl 1 Dispersant 16 1 29 60
  • Example 68 Pigment Blue 15: 3 9 Yl 1 Dispersant 17 1 29 60
  • Example 69 Pigment Blue 15: 3 9 Yl 1 Dispersant 21 1 29 60
  • Example 70 Pigment Blue 15: 3 9 Yl 1 Dispersant 23 1 29 60
  • Example 69 Pig
  • Example 90 Pigment Red 57 1 9 Y10 1 Dispersant 23 2 28 60
  • Example 91 Pigment Red 57 1 9 Y10 1 Dispersant 24 2 28 60
  • Example 92 Pigment Red 57 1 9 Y10 1 Dispersant 25 2 28 60
  • Example 93 Pigment Red 57 1 9 Y10 1 Dispersant 26 2 28 60
  • Example 94 Pigment Red 57 1 9 Y10 1 Dispersant 27 2 28 60
  • Example 95 Pigment Red 57 1 9 Y10 1 Dispersant 28 2 28 60
  • Example 96 Pigment Red 57 1 9 Y10 1 Dispersant 29 2 28 60
  • Example 97 Pigment Red 57 1 9 Y10 1 Dispersant 30 2 28 60
  • Example 98 Pigment Red 57 1 9 Y10 1 Dispersant 31 2 28 60
  • Example 99 Pigment Green 36 8 Y2 2 Dispersant 36 2 28 60
  • Example 100 Pigment Green 36 8 Y2 2 Dispersant 37 2 28 60
  • Example 101 Pigment Green 36
  • Example 60 110 100 1.10 ⁇ ⁇ Example 61 100 100 1.00 ⁇ 0
  • Example 62 100 95 1.05 ⁇ ⁇
  • Example 63 95 90 1.06 ⁇ ⁇
  • Example 64 85 85 1.00 ⁇ 0
  • Example 65 130 125 1.04 ⁇ ⁇
  • Example 66 120 115 1.04 ⁇ ⁇
  • Example 67 180 150 1.20 ⁇ ⁇
  • Example 68 200 150 1.33 ⁇ ⁇
  • Example 69 150 130 1.15 ⁇ 0
  • Example 70 160 145 1.10 ⁇ ⁇ Example 71 200 180 1.11 ⁇ 0
  • Example 72 220 210 1.05 0 ⁇
  • Example 73 160 150 1.07 ⁇ ⁇
  • Example 74 300 260 1.15 ⁇ ⁇
  • Example 75 400 320 1.25 ⁇ ⁇
  • Example 76 350 330 1.06 0 ⁇
  • Example 77 310 300 1.03 ⁇ 0
  • Example 78 140 140 1.00 ⁇ 0
  • Example 79 160 150 1.07
  • Example 90 300 270 1.11 0 ⁇
  • Example 100 330 300 1.10 ⁇ ⁇
  • Example 101 350 340 1.03 ⁇ 0
  • Example 103 250 210 1.19 ⁇ ⁇
  • Example 117 120 100 1.20 0 ⁇
  • Example 119 300 290 1.03 ⁇ ⁇
  • Example 60 pigment dispersions were obtained according to the blending ratios (weight ratios) shown in Table 12.
  • the evaluation was made in the same manner as in Example 60 (the lower the viscosity, the better, the closer the TI value is to 1, the better).
  • ⁇ , ⁇ 1 if the rate of change in viscosity before and after storage at 50 ° C for 1 week is within ⁇ 10%
  • it was set as X.
  • the coating weight loss is 200 after removing the coating film and solvent on the glass.
  • C, ⁇ if the weight loss before and after heating for 1 hour is within 10%, and X if it exceeds 10%.
  • Table 13 The results are shown in Table 13.
  • Comparative Example 12 200 200 1. 00 ⁇ X
  • Comparative example 19 350 300 1.17 ⁇ X
  • Comparative example 20 400 330 1.21 ⁇ X
  • the pigment dispersions of Examples 60 to 119 using the polyester dispersant of the present invention have a low initial viscosity and are excellent with little increase in viscosity over time. Stability. In addition, the coating has high resistance. On the other hand, in the pigment dispersions of Comparative Examples 8 to 24, the amount of the dispersant having a high viscosity must be increased. Also, since many dispersants with low molecular weight were used, it was obvious that there was a problem with the durability of the coating film even though there was no problem with the viscosity.
  • the polyester dispersant according to the present invention can be suitably used in fields such as paints and colored resin compositions, and specifically includes offset inks, gravure inks, color filter resist inks, and the like. It can be suitably used for ink jet inks.
  • the polyester dispersant of the present invention is used, a dispersion excellent in non-aggregability, fluidity and storage stability can be produced.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polymerisation Methods In General (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un dispersant polyester, obtenu en faisant réagir un groupement hydroxyle dans un polymère de vinyle (a) comportant deux groupements hydroxyle dans une de ses régions terminales et éventuellement un groupement hydroxyle dans un composé polyol (c) autre que le polymère de vinyle (a) avec un groupement anhydride acide dans un acide tétracarboxylique anhydre (b) et éventuellement un groupement anhydride acide dans un acide tricarboxylique anhydre (d). Le polymère de vinyle (a) est obtenu par polymérisation radicalaire d'un monomère à insaturation éthylénique en présence d'un composé (a1) comportant deux groupements hydroxyle et un groupement thiol dans sa molécule. L'invention concerne également un procédé de fabrication du dispersant polyester. Le dispersant polyester présente d'excellentes propriétés de dispersion, une excellente fluidité et une excellente stabilité au stockage, même lorsqu'il est utilisé en petite quantité. Le dispersant polyester convient pour une encre lithographique, une encre hélio, une encre de réserve pour un filtre coloré, une encre pour impression jet d'encre, un revêtement, une composition de résine colorée et analogues.
PCT/JP2007/063997 2006-07-14 2007-07-13 Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant WO2008007776A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2008524858A JP4396777B2 (ja) 2006-07-14 2007-07-13 ポリエステル分散剤とその製造方法、及びそれを用いた顔料組成物
KR1020097002686A KR101354265B1 (ko) 2006-07-14 2007-07-13 폴리에스테르 분산제와 그의 제조방법, 및 그것을 이용한 안료 조성물
CN2007800267222A CN101490128B (zh) 2006-07-14 2007-07-13 聚酯分散剂及其制备方法、以及使用该分散剂的颜料组合物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2006193704 2006-07-14
JP2006-193704 2006-07-14
JP2007064446 2007-03-14
JP2007-064446 2007-03-14

Publications (1)

Publication Number Publication Date
WO2008007776A1 true WO2008007776A1 (fr) 2008-01-17

Family

ID=38923332

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/063997 WO2008007776A1 (fr) 2006-07-14 2007-07-13 Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant

Country Status (5)

Country Link
JP (1) JP4396777B2 (fr)
KR (1) KR101354265B1 (fr)
CN (1) CN101490128B (fr)
TW (1) TWI427100B (fr)
WO (1) WO2008007776A1 (fr)

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009165910A (ja) * 2008-01-11 2009-07-30 Toyo Ink Mfg Co Ltd 分散剤、及びそれを用いた顔料組成物並びに顔料分散体
JP2009235323A (ja) * 2008-03-28 2009-10-15 Konica Minolta Ij Technologies Inc 水系インクジェット記録用インクとそれを用いたインクジェット画像形成方法
JP2009251481A (ja) * 2008-04-10 2009-10-29 Toyo Ink Mfg Co Ltd カラーフィルタ用緑色着色組成物及びカラーフィルタ
JP2009251482A (ja) * 2008-04-10 2009-10-29 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物およびカラーフィルタ
JP2010163500A (ja) * 2009-01-14 2010-07-29 Toyo Ink Mfg Co Ltd 顔料分散体およびインキ
JP2010195949A (ja) * 2009-02-26 2010-09-09 Toyo Ink Mfg Co Ltd 分散剤とその製造方法、及びそれを用いた顔料組成物
JP2010223988A (ja) * 2009-03-19 2010-10-07 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物及びカラーフィルタ
CN101859068A (zh) * 2009-02-13 2010-10-13 东洋油墨制造株式会社 滤色器用着色组合物和滤色器
JP2010254746A (ja) * 2009-04-22 2010-11-11 Toyo Ink Mfg Co Ltd 印刷インキ、およびカラーフィルタ基板
CN101353421B (zh) * 2008-09-17 2010-12-08 武汉工程大学 一种聚酯型超支化聚合物颜料分散剂及其制备方法
JP2011157416A (ja) * 2010-01-29 2011-08-18 Toyo Ink Sc Holdings Co Ltd 硬化性分散剤、及びそれを用いた顔料組成物並びに顔料分散体
JP2012036379A (ja) * 2010-07-14 2012-02-23 Toyo Ink Sc Holdings Co Ltd 顔料用分散剤、及びそれを用いた顔料組成物
JP2012036380A (ja) * 2010-07-14 2012-02-23 Toyo Ink Sc Holdings Co Ltd 顔料用分散剤、及びそれを用いた顔料組成物
JP2012093438A (ja) * 2010-10-25 2012-05-17 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用感光性着色組成物及びカラーフィルタ
US8343997B2 (en) 2008-12-19 2013-01-01 Sirtris Pharmaceuticals, Inc. Thiazolopyridine sirtuin modulating compounds
JP2013160783A (ja) * 2012-02-01 2013-08-19 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用着色組成物の製造方法、カラーフィルタ用着色組成物およびカラーフィルタ
JP2014218589A (ja) * 2013-05-09 2014-11-20 大日精化工業株式会社 顔料着色剤組成物及びそれに用いる末端カルボキシル基含有アクリル系ポリマーの製造方法
JP2015007802A (ja) * 2014-08-29 2015-01-15 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
JP2015114588A (ja) * 2013-12-13 2015-06-22 東洋インキＳｃホールディングス株式会社 光散乱層用樹脂組成物、光散乱層、および有機エレクトロルミネッセンス装置
KR20160094382A (ko) 2013-12-05 2016-08-09 토요잉크Sc홀딩스주식회사 안료 조성물 및 그 제조방법, 마쇄 혼련용의 수용성 유기 용제, 및 컬러 필터용 안료 조성물
JP2016164614A (ja) * 2015-03-06 2016-09-08 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、カラーフィルタ、およびカラーフィルタ用分散剤
WO2017122695A1 (fr) 2016-01-14 2017-07-20 東洋インキＳｃホールディングス株式会社 Composition de coloration thermodurcissable et procédé de production de filtre coloré pour éléments d'imagerie à semi-conducteurs
WO2017130812A1 (fr) 2016-01-29 2017-08-03 東洋インキＳｃホールディングス株式会社 Composition électroconductrice, procédé de production associé, et matériau électroconducteur
JP2017165820A (ja) * 2016-03-14 2017-09-21 東洋インキＳｃホールディングス株式会社 カラーフィルタ用顔料組成物、着色組成物、カラーフィルタおよびカラーフィルタ用顔料組成物の製造方法
JP2017187587A (ja) * 2016-04-05 2017-10-12 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物およびカラーフィルタ
WO2018030506A1 (fr) * 2016-08-10 2018-02-15 東洋インキＳｃホールディングス株式会社 Composition de pigment, matériau de revêtement contenant cette composition de pigment, et agent de dispersion
JP2019078878A (ja) * 2017-10-24 2019-05-23 東洋インキＳｃホールディングス株式会社 カラーフィルタ用感光性組成物、及びカラーフィルタ
WO2019230539A1 (fr) 2018-05-31 2019-12-05 東洋インキＳｃホールディングス株式会社 Composition colorante et procédé de production de filtre coloré destiné à une utilisation dans un élément d'imagerie à semi-conducteurs
CN113376964A (zh) * 2016-09-02 2021-09-10 住友化学株式会社 着色组合物及化合物
WO2022019255A1 (fr) * 2020-07-22 2022-01-27 富士フイルム株式会社 Composition de résine, film, filtre optique, élément d'imagerie à l'état solide, dispositif d'affichage d'images et résine
JP2022136141A (ja) * 2018-05-17 2022-09-15 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
JP7439391B2 (ja) 2019-04-19 2024-02-28 ａｒｔｉｅｎｃｅ株式会社 接着剤組成物及びその製造方法、積層フィルム並びに包装体
CN113376963B (zh) * 2016-09-02 2024-05-28 住友化学株式会社 着色组合物及化合物

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009165925A (ja) * 2008-01-11 2009-07-30 Toyo Ink Mfg Co Ltd ポリエステル分散剤、およびそれを用いた顔料組成物
JP5605324B2 (ja) * 2010-07-14 2014-10-15 東洋インキＳｃホールディングス株式会社 顔料用分散剤、及びそれを用いた顔料組成物
CN103374240A (zh) * 2012-04-13 2013-10-30 Jsr株式会社 着色组合物、滤色器及显示元件
CN103937332B (zh) * 2014-04-18 2016-01-20 广州艾科新材料股份有限公司 一种低voc环保聚氨酯色浆
JP6589305B2 (ja) * 2015-03-13 2019-10-16 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、およびカラーフィルタ
CN104974587B (zh) * 2015-06-05 2018-07-06 武汉金弘扬化工科技有限公司 水性体系颜料用双子型非离子高分子分散剂、其制备方法、其应用及水性涂料
WO2018097279A1 (fr) * 2016-11-28 2018-05-31 東洋インキＳｃホールディングス株式会社 Polymère (méth)acrylique, copolymère séquencé (méth)acrylique, dispersion de pigment, composition colorante photosensible, filtre coloré, composition d'encre, copolymère séquencé composite, agent de dispersion de pigment, et agent de revêtement
WO2021192883A1 (fr) * 2020-03-25 2021-09-30 Dic株式会社 Stabilisateur de dispersion de charge inorganique, composition de résine contenant une charge inorganique, article moulé et additif

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6161623A (ja) * 1984-08-31 1986-03-29 Dainippon Ink & Chem Inc 顔料分散剤
JPH01141968A (ja) * 1987-11-30 1989-06-02 Nippon Oil & Fats Co Ltd 顔料分散剤
JPH02219866A (ja) * 1989-02-22 1990-09-03 Nippon Oil & Fats Co Ltd 顔料分散剤
JPH09157538A (ja) * 1995-12-08 1997-06-17 Daicel Chem Ind Ltd 顔料分散剤およびこれを含む塗料もしくは印刷インキ組成物
JPH10500446A (ja) * 1994-05-17 1998-01-13 イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー 櫛状顔料分散剤
JP2000063404A (ja) * 1998-08-25 2000-02-29 Mitsubishi Chemicals Corp 光重合性組成物の製造方法
JP2000239376A (ja) * 1999-02-19 2000-09-05 Dainippon Toryo Co Ltd 水性塗料用顔料分散剤の製造方法
JP2000239308A (ja) * 1999-02-24 2000-09-05 Soken Chem & Eng Co Ltd アクリル系重合体、硬化性組成物、硬化体およびこれらの用途
JP2002226566A (ja) * 2001-02-06 2002-08-14 Nippon Shokubai Co Ltd ポリエーテルポリエステルの製造方法
WO2007007685A1 (fr) * 2005-07-08 2007-01-18 Toyo Ink Manufacturing Co., Ltd. Agent dispersant, procédé de production de cet agent et de dispersion de pigment et encre contenant un tel agent dispersant

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1053125C (zh) * 1996-05-27 2000-06-07 华东理工大学 一种聚酯型分散剂及其制备方法
JP3588938B2 (ja) * 1996-10-23 2004-11-17 東レ株式会社 顔料分散液、カラーペーストおよびカラーフィルター
AU8506298A (en) * 1997-07-25 1999-02-16 Ici Americas Inc. Dispersing agents and dispersions made therefrom
JP4788935B2 (ja) * 2000-04-27 2011-10-05 綜研化学株式会社 分子末端に重合性不飽和基を有するアクリル系重合体

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6161623A (ja) * 1984-08-31 1986-03-29 Dainippon Ink & Chem Inc 顔料分散剤
JPH01141968A (ja) * 1987-11-30 1989-06-02 Nippon Oil & Fats Co Ltd 顔料分散剤
JPH02219866A (ja) * 1989-02-22 1990-09-03 Nippon Oil & Fats Co Ltd 顔料分散剤
JPH10500446A (ja) * 1994-05-17 1998-01-13 イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー 櫛状顔料分散剤
JPH09157538A (ja) * 1995-12-08 1997-06-17 Daicel Chem Ind Ltd 顔料分散剤およびこれを含む塗料もしくは印刷インキ組成物
JP2000063404A (ja) * 1998-08-25 2000-02-29 Mitsubishi Chemicals Corp 光重合性組成物の製造方法
JP2000239376A (ja) * 1999-02-19 2000-09-05 Dainippon Toryo Co Ltd 水性塗料用顔料分散剤の製造方法
JP2000239308A (ja) * 1999-02-24 2000-09-05 Soken Chem & Eng Co Ltd アクリル系重合体、硬化性組成物、硬化体およびこれらの用途
JP2002226566A (ja) * 2001-02-06 2002-08-14 Nippon Shokubai Co Ltd ポリエーテルポリエステルの製造方法
WO2007007685A1 (fr) * 2005-07-08 2007-01-18 Toyo Ink Manufacturing Co., Ltd. Agent dispersant, procédé de production de cet agent et de dispersion de pigment et encre contenant un tel agent dispersant

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009165910A (ja) * 2008-01-11 2009-07-30 Toyo Ink Mfg Co Ltd 分散剤、及びそれを用いた顔料組成物並びに顔料分散体
JP2009235323A (ja) * 2008-03-28 2009-10-15 Konica Minolta Ij Technologies Inc 水系インクジェット記録用インクとそれを用いたインクジェット画像形成方法
JP2009251481A (ja) * 2008-04-10 2009-10-29 Toyo Ink Mfg Co Ltd カラーフィルタ用緑色着色組成物及びカラーフィルタ
JP2009251482A (ja) * 2008-04-10 2009-10-29 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物およびカラーフィルタ
CN101353421B (zh) * 2008-09-17 2010-12-08 武汉工程大学 一种聚酯型超支化聚合物颜料分散剂及其制备方法
US8492401B2 (en) 2008-12-19 2013-07-23 Glaxosmithkline Llc Thiazolopyridine sirtuin modulating compounds
US8343997B2 (en) 2008-12-19 2013-01-01 Sirtris Pharmaceuticals, Inc. Thiazolopyridine sirtuin modulating compounds
JP2010163500A (ja) * 2009-01-14 2010-07-29 Toyo Ink Mfg Co Ltd 顔料分散体およびインキ
CN101859068A (zh) * 2009-02-13 2010-10-13 东洋油墨制造株式会社 滤色器用着色组合物和滤色器
JP2010195949A (ja) * 2009-02-26 2010-09-09 Toyo Ink Mfg Co Ltd 分散剤とその製造方法、及びそれを用いた顔料組成物
JP2010223988A (ja) * 2009-03-19 2010-10-07 Toyo Ink Mfg Co Ltd カラーフィルタ用着色組成物及びカラーフィルタ
JP2010254746A (ja) * 2009-04-22 2010-11-11 Toyo Ink Mfg Co Ltd 印刷インキ、およびカラーフィルタ基板
JP2011157416A (ja) * 2010-01-29 2011-08-18 Toyo Ink Sc Holdings Co Ltd 硬化性分散剤、及びそれを用いた顔料組成物並びに顔料分散体
JP2012036379A (ja) * 2010-07-14 2012-02-23 Toyo Ink Sc Holdings Co Ltd 顔料用分散剤、及びそれを用いた顔料組成物
JP2012036380A (ja) * 2010-07-14 2012-02-23 Toyo Ink Sc Holdings Co Ltd 顔料用分散剤、及びそれを用いた顔料組成物
JP2012093438A (ja) * 2010-10-25 2012-05-17 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用感光性着色組成物及びカラーフィルタ
JP2013160783A (ja) * 2012-02-01 2013-08-19 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用着色組成物の製造方法、カラーフィルタ用着色組成物およびカラーフィルタ
JP2014218589A (ja) * 2013-05-09 2014-11-20 大日精化工業株式会社 顔料着色剤組成物及びそれに用いる末端カルボキシル基含有アクリル系ポリマーの製造方法
KR20160094382A (ko) 2013-12-05 2016-08-09 토요잉크Sc홀딩스주식회사 안료 조성물 및 그 제조방법, 마쇄 혼련용의 수용성 유기 용제, 및 컬러 필터용 안료 조성물
JP2015114588A (ja) * 2013-12-13 2015-06-22 東洋インキＳｃホールディングス株式会社 光散乱層用樹脂組成物、光散乱層、および有機エレクトロルミネッセンス装置
JP2015007802A (ja) * 2014-08-29 2015-01-15 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
JP2016164614A (ja) * 2015-03-06 2016-09-08 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物、カラーフィルタ、およびカラーフィルタ用分散剤
WO2017122695A1 (fr) 2016-01-14 2017-07-20 東洋インキＳｃホールディングス株式会社 Composition de coloration thermodurcissable et procédé de production de filtre coloré pour éléments d'imagerie à semi-conducteurs
US10915028B2 (en) 2016-01-14 2021-02-09 Toyo Ink Sc Holdings Co., Ltd. Thermosetting coloring composition and method of producing color filter for solid-state imaging element
WO2017130812A1 (fr) 2016-01-29 2017-08-03 東洋インキＳｃホールディングス株式会社 Composition électroconductrice, procédé de production associé, et matériau électroconducteur
JP2017165820A (ja) * 2016-03-14 2017-09-21 東洋インキＳｃホールディングス株式会社 カラーフィルタ用顔料組成物、着色組成物、カラーフィルタおよびカラーフィルタ用顔料組成物の製造方法
JP2017187587A (ja) * 2016-04-05 2017-10-12 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物およびカラーフィルタ
WO2018030506A1 (fr) * 2016-08-10 2018-02-15 東洋インキＳｃホールディングス株式会社 Composition de pigment, matériau de revêtement contenant cette composition de pigment, et agent de dispersion
JP7217777B2 (ja) 2016-09-02 2023-02-03 住友化学株式会社 着色組成物及び化合物
JP7315621B2 (ja) 2016-09-02 2023-07-26 住友化学株式会社 着色組成物
CN113376964A (zh) * 2016-09-02 2021-09-10 住友化学株式会社 着色组合物及化合物
CN113376963A (zh) * 2016-09-02 2021-09-10 住友化学株式会社 着色组合物及化合物
JP2021155746A (ja) * 2016-09-02 2021-10-07 住友化学株式会社 着色組成物及び化合物
JP2021155748A (ja) * 2016-09-02 2021-10-07 住友化学株式会社 着色組成物及び化合物
JP2021155749A (ja) * 2016-09-02 2021-10-07 住友化学株式会社 着色組成物及び化合物
JP2021167412A (ja) * 2016-09-02 2021-10-21 住友化学株式会社 着色組成物及び化合物
CN113376963B (zh) * 2016-09-02 2024-05-28 住友化学株式会社 着色组合物及化合物
CN113376964B (zh) * 2016-09-02 2024-04-26 住友化学株式会社 着色组合物及化合物
JP7217774B2 (ja) 2016-09-02 2023-02-03 住友化学株式会社 着色組成物及び化合物
JP7217776B2 (ja) 2016-09-02 2023-02-03 住友化学株式会社 着色組成物及び化合物
JP2019078878A (ja) * 2017-10-24 2019-05-23 東洋インキＳｃホールディングス株式会社 カラーフィルタ用感光性組成物、及びカラーフィルタ
JP2022136141A (ja) * 2018-05-17 2022-09-15 東洋インキＳｃホールディングス株式会社 カラーフィルタ用着色組成物及びカラーフィルタ
WO2019230539A1 (fr) 2018-05-31 2019-12-05 東洋インキＳｃホールディングス株式会社 Composition colorante et procédé de production de filtre coloré destiné à une utilisation dans un élément d'imagerie à semi-conducteurs
JP7439391B2 (ja) 2019-04-19 2024-02-28 ａｒｔｉｅｎｃｅ株式会社 接着剤組成物及びその製造方法、積層フィルム並びに包装体
CN115702213A (zh) * 2020-07-22 2023-02-14 富士胶片株式会社 树脂组合物、膜、滤光器、固体摄像元件、图像显示装置及树脂
WO2022019255A1 (fr) * 2020-07-22 2022-01-27 富士フイルム株式会社 Composition de résine, film, filtre optique, élément d'imagerie à l'état solide, dispositif d'affichage d'images et résine

Also Published As

Publication number Publication date
KR101354265B1 (ko) 2014-01-22
CN101490128B (zh) 2011-11-30
KR20090029293A (ko) 2009-03-20
JPWO2008007776A1 (ja) 2009-12-10
TW200829618A (en) 2008-07-16
JP4396777B2 (ja) 2010-01-13
TWI427100B (zh) 2014-02-21
CN101490128A (zh) 2009-07-22

Similar Documents

Publication Publication Date Title
WO2008007776A1 (fr) Dispersant polyester, son procédé de fabrication et composition de pigment l'utilisant
JP5181664B2 (ja) 硬化性分散剤とその製造方法、及びそれを用いた顔料組成物
JP4930494B2 (ja) 顔料組成物
JP5672706B2 (ja) 硬化性分散剤、及びそれを用いた顔料組成物並びに顔料分散体
JP4020150B1 (ja) 分散剤、その製造方法、及び該分散剤を含む顔料分散体
JP5396712B2 (ja) 分散剤、及びそれを用いた顔料組成物並びに顔料分散体
JP5140967B2 (ja) 顔料組成物
JP6577946B2 (ja) 芳香族分散剤組成物
JP2009165925A (ja) ポリエステル分散剤、およびそれを用いた顔料組成物
US11879032B2 (en) Reaction products containing urethane groups and urea groups
JP5857483B2 (ja) 顔料用分散剤、及びそれを用いた顔料組成物
JP2008200664A (ja) 分散剤とその製造方法、及びそれを用いた顔料組成物
JP5605324B2 (ja) 顔料用分散剤、及びそれを用いた顔料組成物
JP2007254556A (ja) 顔料組成物および顔料分散体
JP5228368B2 (ja) ビニル系分散剤、その製造方法、及びそれを用いた顔料分散体
JP2008019368A (ja) 顔料組成物
WO2018030506A1 (fr) Composition de pigment, matériau de revêtement contenant cette composition de pigment, et agent de dispersion
JP5857484B2 (ja) 顔料用分散剤、及びそれを用いた顔料組成物
JP4525755B2 (ja) 分散剤とその製造方法、及びそれを用いた顔料組成物
JP2009185279A (ja) 分散剤とその製造方法、及びそれを用いた顔料組成物
JP2007314617A (ja) ビニル系共重合体とその製造方法、およびそれを用いた顔料組成物
JP2018028059A (ja) 顔料組成物、該顔料組成物を含む塗料及び樹脂
JP4957351B2 (ja) 磁気記録媒体用塗料組成物及びそれを用いてなる磁気記録媒体
JP2009167304A (ja) インクジェットインキ
JP2009167305A (ja) インクジェットインキ

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200780026722.2

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07790777

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008524858

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 1020097002686

Country of ref document: KR

NENP Non-entry into the national phase

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 07790777

Country of ref document: EP

Kind code of ref document: A1