JP2002226587A - Polymer, pigment-dispersed composition and colored light- sensitive composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymer having a new structure useful for obtaining a pigment disperser capable of achieving stable and good dispersibility and fluidity without coagulating the pigment, and also having excellent light permeability, and further to provide a pigment-dispersed composition containing the polymer, having excellent pigment dispersibility, fluidity or the like, further having high tinting power and excellent properties for alkali development, and suitably usable in a wide range of a coating material, a printing ink, a color signboard or the like. SOLUTION: This polymer is a graft-type polymer formed by an addition reaction of a polymer having a repeating unit containing a primary or secondary amino group, to a polymer having an ethylenically unsaturated double bond at one terminal. The pigment-dispersed composition is obtained by dispersing an organic pigment and the graft-type polymer in an organic solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel polymer useful as a pigment dispersant, a pigment dispersion composition containing the polymer, and a colored photosensitive composition. A novel polymer that prevents the pigment from dispersing and realizes a good dispersion of the pigment, containing the polymer, is excellent in pigment dispersibility, fluidity, etc., and is also excellent in coloring power, paint, printing ink,
A pigment dispersion composition that can be suitably used in a wide range such as a color display panel, and a composition containing the pigment dispersion composition, which is used for forming a multicolor image on a substrate such as a color proof or for a liquid crystal color display. The present invention relates to a colored photosensitive composition that can be suitably used for producing a color filter, a photomask, and the like.

[0002]

2. Description of the Related Art Conventionally, pigments exhibit a vivid color tone and high coloring power, and have been widely used in many fields.
Among these pigments, those which are practically important are generally fine particles, and a clear color tone and high coloring power can be obtained by preventing the pigments from agglomerating and miniaturizing them. However, as the pigment is further refined, the dispersion of the pigment often exhibits a higher viscosity. For this reason, when this pigment dispersion is prepared on an industrial scale, it becomes difficult to take out the pigment dispersion from the dispersing machine, or it becomes impossible to transport by a pipeline, and further, gelation occurs during storage. There is a problem that it cannot be used.

[0003] Colored photosensitive compositions containing the above pigments are useful as materials for color filters used in liquid crystal displays and the like. A pigment dispersion method which is excellent in terms of production stability and the like is widely used. In this pigment dispersion method, a coating solution of the colored photosensitive composition is applied on a transparent substrate to provide a colored photosensitive layer, and after pattern exposure, development is performed to form a first color pixel pattern,
This is repeated a plurality of times to form pixel patterns of a plurality of colors on the transparent substrate.

However, since a pigment is used here as a coloring material, if the pigment is not finely divided, light is scattered and absorbed by the pigment, and the light transmittance is reduced. Further, there is a problem that the polarization axis is rotated due to light scattering, birefringence, etc. by the pigment, and the contrast of the liquid crystal display device is also reduced (the 7th color optical conference in 1990, 512 color display 10. 4 "size TFT-LC
D color filter, Ueki, Koseki, Fukunaga, Yamanaka). For this reason, in the colored photosensitive composition, it is necessary to disperse the pigment in a highly fine state.

Therefore, it is conventionally known to use various dispersants in order to obtain a pigment dispersion or a colored photosensitive composition having excellent fluidity and dispersibility. The dispersants can be broadly classified into polymer dispersants and low molecular compound dispersants. Examples of the polymer dispersants include polyacrylates, sodium maleate olefin copolymers, and polyesters having a terminal carboxyl group (Japanese Patent Publication No. 54-34
009), a polyester having an acidic group and / or a basic group starting from tetrakis (2-hydroxyalkyl) ethylenediamine (JP-A-2-2452).
No. 31), a macromonomer (an oligomer having an ethylenically unsaturated group at a terminal), a monomer having a hydroxyl group,
Copolymers comprising four kinds of carboxy group-containing monomers and other monomers (Japanese Patent Application Laid-Open No. Hei 8-259876) are known, and the low-molecular-weight compound dispersants include sorbitan fatty acid esters, Ethylene alkylamines, alkyldiamines, alkanolamine derivatives (US Pat. No. 3,536,510) are known.

Among these dispersants, JP-A-7-14
No. 0654, JP-A-5-273411 and JP-A-8-259876 disclose that a colored photosensitive composition as a material for a color filter, a color proof or the like includes a macromonomer (an ethylenic non-terminated compound). It is disclosed that a pigment dispersion having a small pigment particle size and excellent dispersion stability can be obtained by using a copolymer containing an oligomer having a saturated group).

However, since the copolymer containing the macromonomer does not contain a functional group that promotes adsorption to the pigment, it does not function alone as a dispersant, and must be used in combination with another dispersant. There's a problem. When the copolymer containing the macromonomer is used as a dispersant, the thickening effect seen in the polymer dispersant is small and good, but the fine particle effect of the pigment is not sufficient, and the dispersibility is not sufficient. There's a problem.

In Japanese Patent Application Laid-Open No. Hei 9-146272, the dispersibility can be improved by using a copolymer containing the macromonomer having an acidic group in a graft portion as a functional group for promoting adsorption to a pigment. I'm trying. However, there is a problem that dispersibility is not sufficient because the steric repulsion effect of the graft portion is reduced. On the other hand, JP-A-10-339949 discloses that a copolymer containing the macromonomer containing a nitrogen atom in a main chain thereof is used as a functional group for promoting adsorption to a pigment, so that the interaction with the pigment is improved. These problems are solved by promoting (adsorption) and effective steric repulsion of the graft portion.

On the other hand, a colored photosensitive composition containing a pigment exhibiting a vivid color tone and high coloring power is useful as an image forming material for producing, for example, a color proof or a color filter. When a colored image is formed using the composition, generally, after a coating solution of the colored photosensitive composition is applied on a substrate to form a layer of the colored photosensitive composition, exposure and development are performed. As a developer used for development, an alkaline aqueous solution having little effect on the environment is often used. Generally, the layer made of the colored photosensitive composition contains a binder that is soluble in an alkaline aqueous solution because the copolymer containing the macromonomer alone has poor solubility in an alkaline aqueous solution. However, since the copolymer containing the macromonomer in JP-A-10-339949 is insoluble in an aqueous alkaline solution, there is a problem that the layer of the colored photosensitive composition has insufficient alkali developability.
It is desired that the copolymer containing the macromonomer is soluble in an alkaline aqueous solution or can be easily dispersed in an alkaline aqueous solution.

However, at present, a pigment dispersion which is excellent in pigment dispersibility and fluidity and is soluble in an aqueous alkali solution, a pigment dispersion composition containing the same, and a colored photosensitive composition have not yet been provided. It is.

[0011]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned conventional problems and achieve the following objects. That is, the present invention provides a pigment having a novel structure useful for obtaining a pigment dispersant that realizes stable and good dispersibility and fluidity of the pigment without aggregating the pigment and also has excellent light transmittance. The purpose is to provide coalescence. Further, the present invention contains the above polymer, excellent dispersibility of pigments, excellent fluidity, etc., and high coloring power, excellent alkali developability, paints, printing inks, a wide range of color display boards and the like An object of the present invention is to provide a pigment dispersion composition that can be suitably used.
Further, the present invention provides a color filter containing the pigment dispersion composition, having high coloring power, excellent alkali developability, forming a multicolor image on a substrate such as a color proof, and a liquid crystal color display. An object of the present invention is to provide a colored photosensitive composition that can be suitably used for the production of, for example.

[0012]

Means for Solving the Problems As a result of intensive studies conducted by the present inventors to solve the above problems, the following findings have been obtained. That is, when an organic pigment is dispersed in a binder having an acidic group soluble in an organic solvent, an intermolecular force acts between the acidic group and the organic pigment, which tends to increase the viscosity. Although the dispersion stability is improved by this thickening, the handleability, workability and the like are reduced, and the organic pigment tends to be hard to be fine. For this reason, a dispersant capable of accelerating dispersion without thickening is desired, and as such a dispersant, a low molecular compound dispersant, particularly an amine compound, etc., is known. However, in the case of the amine compound or the like, an acid group and a salt are formed, and the photosensitive resin layer is easily dissolved in a developing solution.
It can adversely affect later development. Alkaline dispersants and water-soluble dispersants also have the same tendency as the above-mentioned amine compounds. On the other hand, in the case of the above-mentioned macromonomer, although the above-mentioned problem of thickening can be suppressed to some extent due to the steric effect of the polymer chain, it is a finding that the dispersibility of the pigment is not sufficient.

The present invention is based on the above findings by the present inventors, and the means for solving the above problems are as follows. That is,

<1> A graft polymer formed by an addition reaction between a polymer having a repeating unit having a primary or secondary amino group and a polymer having an ethylenically unsaturated double bond at one end. .

<2> The graft type according to <1>, wherein the terminal group of the polymer having an ethylenically unsaturated double bond at one end is selected from an acryloyl group, a methacryloyl group, an acrylamide group and a methacrylamide group. It is a polymer.

<3> The polymer according to <1> or <2>, wherein the polymer having a repeating unit having a primary or secondary amino group is selected from polyethyleneimine and a polymer having a polyvinylamine polyallylamine unit. It is a graft polymer.

<4> A pigment dispersion composition comprising an organic pigment and a graft polymer of <1> to <3> dispersed in an organic solvent.

<5> A pigment dispersion composition according to <4>, comprising a binder polymer having an acidic group, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. It is a colored photosensitive composition.

[0019]

DESCRIPTION OF THE PREFERRED EMBODIMENTS << Polymer >> The polymer of the present invention comprises 1
It is a graft polymer formed by bonding a polymer having a repeating unit having a primary or secondary amine group and a polymer having an ethylenically unsaturated double bond at one end by an addition reaction.

(Polymer Having Repeating Unit Having Primary or Secondary Amino Group) The polymer having a repeating unit having a primary or secondary amino group may be a homopolymer of polyethyleneimine, polyvinylamine, or polyallylamine. It is preferable to be selected from copolymers of these and other polymerizable monomers.

The content of the repeating unit having a primary or secondary amino group in the polymer having a repeating unit having a primary or secondary amino group is preferably from 10% by mass to 100% by mass, more preferably 20% by mass. From 10
0 mass% is more preferable. When the content is 10% by mass or more, aggregation of the pigment can be prevented, and an increase in viscosity can be suppressed.

Polyethyleneimine, polyvinylamine,
Examples of monomers copolymerizable with the polyallylamine unit include unsaturated carboxylic acids (eg, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid and fumaric acid), aromatic vinyl compounds (eg, styrene, α- Methylstyrene, p-
Hydroxystyrene, chloromethylstyrene and vinyltoluene), alkyl (meth) acrylates (eg, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate), alkylaryl (meth) acrylate (eg, benzyl (meth) acrylate), alkyl (meth) acrylate-substituted alkyl ester (eg,
Glycidyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate and dimethylaminopropyl (meth)
Acrylate), alkyl (meth) acrylamide,
(Examples: (meth) acrylamide, dimethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, n-butyl (meth) acrylamide, tert-butyl (meth) acrylamide and tert-octyl (meth) acrylamide), substituted alkyl ( (Meth) acrylamide (eg, dimethylaminoethyl (meth) acrylamide and dimethylaminopropyl (meth) acrylamide), vinyl cyanide (eg, 1,3-butadiene and isoprene) and polymerizable oligomer (eg, methacryloylated polymethyl at one end) Methacrylate oligomers, one-terminal methacryloylated polystyrene oligomers, and one-terminal methacryloylated polyethylene glycol).

The polystyrene equivalent number average molecular weight (Mn) of the polymer having a repeating unit having a primary or secondary amino group is preferably from 100 to 10,000, more preferably from 200 to 4,000. , 200 to 2,000. When the number average molecular weight is 100 to 10,000,
By preventing the aggregation of the pigment, a rise in viscosity can be suppressed, and sufficient development suitability in the production of a color filter or the like can be obtained.

The content of the polymer having a repeating unit having a primary or secondary amino group in the graft polymer is preferably from 1% by mass to 80% by mass.
1.5 mass% to 60 mass% is more preferable. When the content is 1% by mass to 80% by mass, a sufficient adsorption force of the graft polymer to the pigment can be maintained. In addition, a sufficient steric repulsion effect as a pigment dispersant can be maintained, and an increase in the viscosity of the dispersion can be suppressed.

(Polymer having an ethylenically unsaturated double bond at one end) The polymer having an ethylenically unsaturated double bond at one end has a number average molecular weight (Mn) in terms of polystyrene of 1,000. From 20,000 to 20,000, more preferably from 2,000 to 10,000. The number average molecular weight is 1,000 to 20,000
If so, a sufficient steric repulsion effect as a pigment dispersant can be maintained, and an increase in the adsorption time to the pigment due to the steric effect can be prevented.

Examples of the polymer having an ethylenically unsaturated double bond at one end include, for example, alkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, styrene, acrylonitrile, vinyl acetate, and butadiene. And a homopolymer or copolymer formed from at least one monomer selected from the group consisting of alkyl (meth) acrylates and polystyrene. In the present invention, these polymers having an ethylenically unsaturated double bond at one end thereof may be substituted with a substituent, and the substituent is not particularly limited, and examples thereof include a halogen atom and the like. No.

Preferred examples of the group having an ethylenically unsaturated double bond include a (meth) acryloyl group, a vinyl group and a (meth) acrylamide group. Of these, a (meth) acryloyl group is particularly preferred. preferable.

In the present invention, among the polymers having an ethylenically unsaturated double bond at one end, a polymer represented by the following general formula (I) is preferable.

[0029]

Embedded image

In the above general formula (I), R ¹ and R
³ represents a hydrogen atom or a methyl group. R ² has 1 to 1 carbon atoms
8 represents an alkylene group which may be substituted by an alcoholic hydroxyl group, preferably an alkylene group having 2 to 4 carbon atoms. Y is a phenyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, or -COOR ⁴ (where R ⁴ is an alcoholic hydroxyl group having 1 to 6 carbon atoms, an alkyl which may be substituted with halogen) Group, phenyl group, or 7 to 7 carbon atoms
Represents 10 arylalkyl groups. And a phenyl group or —COOR ⁴ (where R ⁴ represents an alkyl group which may be substituted with an alcoholic hydroxyl group having 1 to 4 carbon atoms). n represents 20 to 200.

Specific examples of the polymer having an ethylenically unsaturated double bond at one end include poly-2hydroxyethyl (meth) acrylate, polystyrene, polymethyl (meth) acrylate, and poly-n-butyl (meth). Preferable examples include acrylate, poly-i-butyl (meth) acrylate, and a copolymer thereof, in which a (meth) acryloyl group is bonded to one molecular terminal.

The polymer having an ethylenically unsaturated double bond at one terminal may be a commercially available product or one synthesized as appropriate. Examples of the commercially available product include methacryloyl at one terminal. Polystyrene oligomer (Mn =
6000, trade name: AS-6, Toa Gosei Chemical Co., Ltd.
), One-terminal methacryloylated polymethyl methacrylate oligomer (Mn = 6000, trade name: AA-6, manufactured by Toagosei Chemical Co., Ltd.), one-terminal methacryloylated poly-
n-butyl acrylate oligomer (Mn = 6000,
Trade name: AB-6, manufactured by Toa Gosei Chemical Co., Ltd.), one-terminal methacryloylated polymethyl methacrylate / 2-hydroxyethyl methacrylate oligomer (Mn = 700)
0, trade name: AA-714, manufactured by Toa Gosei Chemical Co., Ltd.)
One-end methacryloylated polybutyl methacrylate / 2
-Hydroxyethyl methacrylate oligomer (Mn =
7000, trade name: 707S, Toa Gosei Chemical Co., Ltd.
), Methacryloylated poly-2-ethylhexyl methacrylate / 2-hydroxyethyl methacrylate oligomer at one end (Mn = 7000, trade name: AY-707)
S, AY-714S, manufactured by Toa Gosei Chemical Co., Ltd.).

The content of the polymer having an ethylenically unsaturated double bond at one end in the above graft polymer is preferably from 20% by mass to 99% by mass, more preferably 20% by mass.
To 98.5% by mass. The content is 20
When the amount is from 99% by mass to 99% by mass, a sufficient steric repulsion as a pigment dispersant and a sufficient adsorption force of the graft polymer to the pigment can be obtained, and an increase in the viscosity of the dispersion can be suppressed.

-Specific Examples of Graft Polymer- Preferred specific examples of the above graft polymer include (1) polyethyleneimine / one-terminal methacryloylated polymethyl (meth) acrylate adduct, and (2) polyethyleneimine /
One-terminal methacryloylated polystyrene adduct, (3) polyethyleneimine / one-terminal methacryloylated poly-n-
Butyl (meth) acrylate adduct, (4) polyethyleneimine / one-terminal methacryloylated copolymer adduct of methyl (meth) acrylate and hydroxyethyl (meth) acrylate, (5) polyethyleneimine / one-terminal methacryloylated n-butyl (Meth) acrylate and hydroxyethyl (meth) acrylate copolymer adduct,
(6) Polyethyleneimine / methacryloylation at one end 2
-Ethylhexyl (meth) acrylate and hydroxyethyl (meth) acrylate copolymer adduct, (7) polyethyleneimine / one-terminal methacryloylated copolymer styrene and acrylonitrile copolymer adduct, (8) polyethyleneimine / one-terminal methacryloylated Polyethylene glycol adduct, (9) polyethyleneimine / one-terminal methacryloylated polypropylene glycol adduct, (10)
Polyethylene imine / one-terminal methacryloylated poly ε-
Caprolactone adduct, (11) polyethyleneimine /
One-terminal methacryloylated methyl (meth) acrylate /
One-terminal methacryloylated polyethylene glycol adduct, (12) polyallylamine / one-terminal methacryloylated polymethyl (meth) acrylate adduct, (13) polyallylamine / one-terminal methacryloylated methyl (meth) acrylate / one-terminal methacryloylated polyethylene glycol adduct Body, (14) polyvinylamine / one-terminal methacryloylated polymethyl (meth) acrylate adduct, (15) polyvinylamine / one-terminal methacryloylated polymethyl (meth) acrylate / one-terminal methacryloylated polyethylene glycol adduct, etc. The present invention is not limited by these.

If necessary, the above graft polymer may contain, as an additional component, a carboxylic acid and its acid halide derivative, acid anhydride or ester derivative in addition to a polymer having an ethylenically unsaturated double bond at only one end. An electrophilic reagent such as an alkyl halide, an isocyanate compound, a compound having an ethylenically unsaturated double bond, or a carbodiimide may be added to a polymer having a repeating unit having a primary or secondary amino group.

Examples of the above carboxylic acids and their acid halide derivatives or ester derivatives include acetic acid, propionic acid, butanoic acid, hexanoic acid, octanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, Acrylic acid, methacrylic acid, itaconic acid, benzoic acid, cinnamic acid, phenylacetic acid, oxalic acid, succinic acid,
Maleic acid, glutaric acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, malonic acid, adipic acid, sebacic acid, trimellitic acid, pyromellitic acid, tartaric acid, methanesulfonic acid, paratoluenesulfonic acid, benzenesulfonic acid, And their acid chlorides, acid bromides, acid anhydrides, methyl esters, ethyl esters, nitrophenyl esters, methoxymethyl esters and the like.

Specific examples of the alkyl halide include chloromethane, bromomethane, iodomethane, bromoethane, iodoethane, 1-bromobutane, 1-bromooctane, 2-ethylhexyl bromide, benzyl chloride, and benzyl bromide.

Specific examples of the above isocyanate compounds include n-butyl isocyanate, tert-butyl isocyanate, adamantyl isocyanate, octyl isocyanate, octadecyl isocyanate, phenyl isocyanate, cyclohexyl isocyanate, xylylene diisocyanate, toluene diisocyanate,
Examples include isophorone diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, and methacryloylethyl isocyanate.

Specific examples of the compound having an ethylenically unsaturated double bond include alkyl (meth) acrylates (eg, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate,
i-butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate), alkyl aryl (meth) acrylate, (eg, benzyl (meth) acrylate), (meth) acrylic acid-substituted alkyl ester (eg, glycidyl ( (Meth) acrylate 2-hydroxyethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate and dimethylaminopropyl (meth) acrylate), alkyl (meth) acrylamide (eg, (meth) acrylamide, dimethyl (meth) acrylamide, n- Isopropyl (meth) acrylamide, n-butyl (meth) acrylamide, tert-butyl (meth) acrylamide and tert-octyl (meth) acrylamide), substituted alkyl (meth) acrylamide (eg, dimethyl Minoethyl (meth) acrylamide and dimethylaminopropyl (meth) acrylamide), vinyl cyanide (eg, (meth) acrylonitrile and α-chloroacrylonitrile), aliphatic conjugated dienes (eg, 1,3-butadiene and isoprene) and the like. Can be

Specific examples of the carbodiimide include dicyclohexylcarbodiimide, diisopropylcarbodiimide, ditert-butylcarbodiimide, 1-cyclohexyl-3- (2-morpholinoethyl) carbodiimide meso-paratoluenesulfonate and the like.

<< Pigment Dispersion Composition >> The pigment dispersion composition of the present invention is obtained by dispersing a pigment dispersant containing the polymer of the present invention and a pigment in an organic solvent.

(Pigment Dispersant) The pigment dispersant of the present invention may contain only the above graft polymer, or may further contain other components appropriately selected as necessary. Examples of the other components include known dispersants, and specifically, nonanoamide, decanamide, dodecaneamide, N-dodecylhexadecamide, N-octadecylpropionamide, N, N-dimethyldodecaneamide, and N, N-dimethyldodecaneamide Amide compounds such as N-dihexylacetamide, amine compounds such as diethylamine, diheptylamine, dibutylhexadecylamine, N, N, N ', N'-tetramethylmethanamine, triethylamine, tributylamine and trioctylamine, monoethanol Amine, diethanolamine, triethanolamine, N, N, N ', N'-(tetrahydroxyethyl)
-1,2-diaminoethane, N, N, N'-tri (hydroxyethyl) -1,2-diaminoethane, N, N,
N ', N'-tetra (hydroxyethylpolyoxyethylene) -1,2-diaminoethane, 1,4-bis (2-
Examples thereof include amines having a hydroxy group such as (hydroxyethyl) piperazine and 1- (2-hydroxyethyl) piperazici, and compounds such as pecotamide, isonipecotamide, and nicotinamide. These may be commercially available products or may be synthesized as appropriate. Examples of the commercially available products include Shigenox-105.
(Trade name, manufactured by Hakkor Chemical Co., Ltd.).

The content of the other components in the pigment dispersant is preferably from 1% by mass to 90% by mass, more preferably from 1% by mass to 70% by mass. When the content is 1% by mass to 90% by mass, the performance as a pigment dispersant is sufficiently exhibited, and the increase in the viscosity of the pigment dispersion composition can be suppressed.

Further, the pigment dispersant of the present invention may contain various surfactants, and if the surfactant is contained, it is effective for improving the dispersion stability. Examples of the surfactant include an anionic surfactant represented by an alkylnaphthalene sulfonate and a phosphoric acid ester salt, a cationic surfactant represented by an amine salt, an aminocarboxylic acid, and a betaine type. And an amphoteric surfactant.

—Dispersion— The term “dispersion with the pigment dispersant” of the present invention means that pigment particles generally present in the form of secondary particles are loosened to form primary particles, thereby preventing reaggregation. The pigment dispersant of the present invention is a graft-type dispersant having a site for adsorption to the pigment and a steric repulsion site for preventing re-aggregation after the pigment is dispersed in the form of primary particles. Even so, it exhibits a sufficiently excellent dispersing effect. In addition, the dispersion of the pigment by the pigment dispersant of the present invention is effectively achieved by direct mixing of the pigment dispersant with the pigment, and is preferably performed in a state in which particles that can be dispersed other than the pigment are present as little as possible. .
When the pigment is dispersed in such a state, the pigment dispersant of the present invention is instantly adsorbed around the pigment particles, and the pigment particles are well dispersed and flow well. Is effectively suppressed. On the other hand, when the pigment is dispersed in a state where particles that can be dispersed other than the pigment particles are present, the pigment dispersant of the present invention is not adsorbed on the surface of the target pigment particles, but is adsorbed on other particle surfaces, The pigment dispersing effect of the pigment dispersant may be impaired. Therefore, for example, in the case of producing a photosensitive material or the like, in order to allow the pigment to be contained in the photosensitive material or the like in a well dispersed state, the pigment and the pigment dispersant of the present invention are mixed at an early stage. It is preferable to add and mix the pigment dispersant of the present invention at a later time, such as when preparing a coating solution for a photosensitive layer.

The pigment dispersant of the present invention can be suitably used for dispersing known pigments, and can be particularly preferably used for the pigment dispersion composition of the present invention and the colored photosensitive composition described below. .

(Organic Pigment) Examples of the pigment include organic pigments. Examples of the organic pigment include a yellow pigment, an orange pigment, a red pigment, a violet pigment, a blue pigment, a green pigment, a brown pigment, a black pigment, and the like.

Examples of the yellow pigment include C.I. I.
Pigment Yellow 20, C.I. I. Pigment Yellow 24, C.I. I. Pigment Yellow 12, C.I. Pigment Yellow 17, C.I. I. Pigment Yellow 83,
C. I. Pigment Yellow 86, C.I. I. Pigment Yellow 93, C.I. I. Pigment Yellow 109,
C. I. Pigment yellow 110, C.I. I. Pigment Yellow 117, C.I. I. Pigment Yellow 12
5, C.I. I. Pigment yellow 137, C.I. I. Pigment yellow 138, C.I. I. Pigment Yellow 1
39, C.I. I. Pigment Yellow 185, C.I. I. Pigment yellow 147, C.I. I. Pigment yellow 148, C.I. Pigment Yellow 153, C.I. I. Pigment yellow, C.I. I. Pigment Yellow 15
4, C.I. I. Pigment yellow 166, C.I. I. Pigment yellow 168, C.I. I. Pigment Yellow 1
85, and the like.

Examples of the orange pigment include C.I.
I. Pigment Orange 36, C.I. I. Pigment Orange 43, C.I. I. Pigment Orange 51, C.I. I.
Pigment Orange 55, C.I. I. Pigment Orange 59, C.I. I. Pigment Orange 61, C.I. I. Pigment Orange 71, and the like.

Examples of the red pigment include C.I. I.
Pigment Red 9, C.I. I. Pigment Red 97,
C. I. Pigment Red 122, C.I. I. Pigment Red 123, C.I. I. Pigment Red 149, C.I.
I. Pigment Red 168, C.I. I. Pigment Red 177, C.I. I. Pigment Red 180, C.I. I.
Pigment Red 192, C.I. I. Pigment Red 2
15, C.I. I. Pigment Red 216, C.I. I. Pigment Red 217, C.I. I. Pigment Red 22
0, C.I. I. Pigment Red 223, C.I. I. Pigment Red 224, C.I. I. Pigment Red 226,
C. I. Pigment Red 227, C.I. I. Pigment Red 228, C.I. I. Pigment Red 240, C.I.
I. Pigment Red 48: 1, C.I. I. Pigment Red 209, C.I. I. Pigment Red 146, C.I.
I. Pigment Red 11, C.I. I. Pigment Red 81, C.I. I. Pigment Red 123, C.I. I. Pigment Red 213, C.I. I. Pigment Red 27
2, C.I. I. Pigment Red 270, C.I. I. Pigment Red 255, C.I. I. Pigment Red 264,
C. I. Pigment Red 254, and the like.

Examples of the violet pigment include:
C. I. Pigment Violet 19, C.I. I. Pigment Violet 23, C.I. I. Pigment Violet 29, C.I. I. Pigment Violet 30, C.I.
I. Pigment Violet 37, C.I. I. Pigmented Violet 40, C.I. I. Pigment Violet 5
0, and the like.

Examples of the blue pigment include C.I. I.
Pigment Blue 15, C.I. I. Pigment Blue 1
5: 6, C.I. I. Pigment Blue 22, C, I.P. Pigment Blue 60, C.I. I. Pigment Blue 64, and the like.

Examples of the green pigment include C.I. I.
Pigment Green 7, C.I. I. Pigment Green 3
6, and the like. Examples of the brown pigment include C.I. I. Pigment Brown 23, C.I. I. Pigment Brown 25, C.I. I. Pigment Brown 2
6, and the like. Examples of the black pigment include C.I. I. Pigment Black 7, and the like.

These pigments may be used alone or in combination of two or more. In the present invention, among these, pigments having an acidic group such as Pigment Yellow 138, Pigment Yellow 139, Pigment Yellow 185, and Pigment Yellow 83 are preferable, and Pigment Yellow 138 and Pigment Yellow 1 are preferable.
39, Pigment Yellow 185, Pigment Red 2
54, Pigment Green 36, Pigment Blue 15
Etc. are particularly preferred.

(Organic Solvent) The organic solvent is not particularly limited and can be appropriately selected from known ones. Examples thereof include ethylene glycol monomethyl ether,
(Poly) alkylene glycol monoalkyl ethers such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether, and ethylene glycol monoethyl ether, and their acetic esters, for example, 1-methoxy-2
-Propyl acetate, 1-ethoxy-2-propyl acetate, etc .; ethyl acetate, n-propyl acetate, i-acetate
Acetates such as propyl, n-butyl acetate and i-butyl acetate; aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as methyl ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone; ethanol, propanol, butanol; Hexanol,
Alcohols such as cyclohexanol, ethylene glycol, diethylene glycol, and glycerin; These may be used alone or in combination of two or more. Among these, alkylene glycol monoalkyl ethers and their acetates, acetates, methyl ethyl ketone, and the like are preferable.

The content of the pigment in the pigment dispersion composition is usually 5% by mass to 80% by mass.
0 mass% to 70 mass% is preferable. The above content is 5
When the amount is from 80% by mass to 80% by mass, a sufficient coloring power can be obtained without increasing the viscosity of the pigment dispersion composition.

The content of the pigment dispersant in the pigment dispersion composition is usually 0.1 to 200 parts by mass, preferably 1 to 50 parts by mass, per 100 parts by mass of the pigment. . When the content is from 0.1 part by mass to 200, the viscosity of the pigment dispersion composition is not increased, and in the case of producing a color filter or the like, a coating film for obtaining chromaticity is used. The thickness can be easily adjusted.

The content of the organic solvent in the pigment dispersion composition is usually from 10 to 2,000 parts by mass, preferably from 20 to 1,000 parts by mass, per 100 parts by mass of the pigment. When the content is 10 parts by mass to 2,000 parts by mass, the viscosity of the pigment dispersion composition does not increase, and the space for storage can be small.

The pigment dispersion composition of the present invention can be prepared, for example, by the following method. 1) A method in which a composition obtained by previously mixing the pigment and the pigment dispersant is added to and dispersed in the organic solvent (or vehicle). 2) The pigment and the pigment are dispersed in the organic solvent (or vehicle). A method of separately adding and dispersing a pigment dispersant 3) a method of previously dispersing the pigment and the pigment dispersant separately in the organic solvent (or vehicle) and mixing the obtained dispersion (in this case, 4) A method of dispersing the pigment in the organic solvent (or vehicle) and then adding the pigment dispersant to the resulting dispersion.

The vehicle refers to a portion of a medium in which the pigment is dispersed when the paint is in a liquid state, and a component (binder) which is liquid and binds to the pigment to solidify the coating film. And a component to be dissolved and diluted (the organic solvent).

The disperser used for dispersing the pigment is not particularly limited, and examples thereof include known dispersers such as a kneader, a roll mill, an attritor, a super mill, a dissolver, a homomixer, and a sand mill.

For the formation of a colored image using the above-mentioned pigment dispersion composition, for example, a coating solution containing the pigment dispersion composition is coated on a support and dried to form a layer of the pigment dispersion composition.
Alternatively, the layer of the pigment dispersion composition formed on the temporary support is transferred onto the support, and a layer of a known positive or negative photosensitive resin composition is formed thereon, and exposed and developed. Then, a method of removing the layer of the pigment dispersion composition in the same region with the unexposed layer of the photosensitive resin composition can be used.

<< Colored Photosensitive Composition >> The colored photosensitive composition contains at least the pigment dispersion composition and the photosensitive composition.

(Photosensitive Composition) Examples of the photosensitive composition include the photosensitive composition described in JP-A-3-282404. Specifically, a negative-type diazo resin and Examples thereof include a photosensitive composition comprising a binder, a photopolymerizable composition, a photosensitive composition comprising an azide compound and a binder, and a cinnamic acid-type photosensitive composition. As the photosensitive composition, those which can be developed with an aqueous alkali solution and those which can be developed with an organic solvent are known. Pollution prevention, those which can be developed with an alkaline aqueous solution in terms of labor safety and the like are known. preferable.

—Photopolymerizable Composition— In the present invention, a photopolymerizable composition is particularly preferable among the above photosensitive compositions. The polymerizable composition contains at least a polyfunctional monomer having two or more ethylenically unsaturated double bonds and a photopolymerizable initiator. If necessary, a binder polymer having an acidic group may be contained.

—Binder Polymer Having Acidic Group— A binder polymer having an acidic group is contained in the photopolymerizable composition in order to impart dispersion stability of the pigment and better alkali developability. For example, (meth) such as methacrylic acid / benzyl methacrylate copolymer and methacrylic acid / methyl methacrylate copolymer
A copolymer of acrylic acid and a (meth) acrylic acid ester, a styrene / maleic anhydride copolymer, and a reaction product of a styrene / maleic anhydride copolymer and an alcohol;
And the like. These may be used alone or in combination of two or more. Among these, excellent pigment dispersibility, polyfunctional monomer, excellent compatibility with the photopolymerization initiator, alkali developer solubility, organic solvent solubility,
Those having appropriate strength and softening temperature are preferred, and specifically, a (meth) acrylic acid / (meth) acrylate copolymer is preferred.

The weight average molecular weight of the binder polymer having an acidic group is preferably from 5,000 to 200,000. The weight average molecular weight is 5000 to 200
If it is 000, the viscosity of the colored photosensitive composition is not increased, and no problem occurs in forming a coating film.

The content of the binder polymer having an acidic group in the colored photosensitive composition is about 20% by mass to 80% by mass based on the total solid content. When the content is 20% by mass to 80% by mass, no problem occurs in the formation of the coating film, and the ability of other materials is exhibited.

--Polyfunctional monomer having two or more ethylenically unsaturated double bonds-- Examples of the polyfunctional monomer having two or more ethylenically unsaturated double bonds include, for example, JP-A-60-258538.
(Meth) acrylate, urethane (meth) acrylate, (meth)
Acrylic amides, allyl compounds, vinyl esters and the like can be mentioned. These may be used alone or in combination of two or more. Among these, (meth) acrylates such as dipentaerythritol hexaacrylate (DPHA) are preferable.

The content of the polyfunctional monomer having an ethylenically unsaturated double bond in the colored photosensitive composition is preferably from 10% by mass to 60% by mass based on the total solid content. When the content is 10% by mass to 60% by mass, the curing power at the time of exposure is not insufficient,
The ability of other materials is also demonstrated.

—Photopolymerization Initiator— The photopolymerization initiator has a wavelength of about 300 to 500 n.
It is preferable to use at least one compound having a molecular extinction coefficient of at least about 50 in m. Examples of such a compound include JP-A-2-48664, JP-A-1-152449, and JP-A-1-152449. 2-1533
No. 53, aromatic ketones,
Lophine dimer, benzoin, benzoin ethers,
And polyhalogens. These may be used alone or in combination of two or more. Among them, a combination of 4,4′-bis (diethylamino) benzophenone and 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, and
[P- (N, N-bis (ethoxycarbonylmethyl) amino) -bromophenyl] -2,6-bis (trichloromethyl) -s-triazine is preferred.

The content of the photopolymerization initiator in the colored photosensitive composition is preferably from 0.2% by mass to 10% by mass based on the solid content of the colored photosensitive composition. When the content is 0.2% by mass to 10% by mass, appropriate exposure sensitivity can be obtained.

The colored photosensitive composition can be prepared, for example, by mixing the pigment dispersion composition and the photosensitive composition according to appropriately selected conditions and techniques.

The formation of a colored image using the above colored photosensitive composition can be basically performed by the following steps (1) to (3). (1) After preparing the pigment dispersion composition, using the same to prepare the colored photosensitive composition (2) coating the obtained colored photosensitive composition on a substrate and drying, or Step of transferring a layer formed by coating and drying on another temporary support onto a substrate to form a layer of a colored photosensitive composition (3) Layer of a colored photosensitive composition formed on a substrate For exposing and developing a pattern to form a pattern

The production of a color filter used for a liquid crystal display or the like can be performed by repeating the above steps (2) and (3) and combining the patterns of the second and subsequent colors. A method for producing a color filter by a transfer method is described in, for example, JP-A-4-208940, JP-A-5-72724, JP-A-5-80503, and JP-A-5-173320.

As the substrate, a transparent material such as a glass plate or a transparent plastic plate is generally used. To improve the adhesion between the substrate and the colored photosensitive composition, various commercially available silane coupling agents or the like are added to the colored photosensitive composition, or the substrate is subjected to a coupling treatment in advance. May be.

The application of the coating solution of the colored photosensitive composition to the substrate can be performed by using a known coating means such as a spin coater, a roll coater, a bar coater, and a curtain coater.

As a method of transferring the layer of the colored photosensitive composition formed on the temporary support onto the substrate, a method using a heat roll laminator under normal pressure or reduced pressure is preferable.

Examples of the developing solution used in the above development include hydroxides or carbonates of alkali metals or alkaline earth metals, hydrogen carbonates, asymonia water, and aqueous solutions of quaternary ammonium salts. Can be These may be used alone or in combination of two or more. Among these, an aqueous solution of sodium carbonate is particularly preferred.

Since the pigment dispersant of the present invention contains an amide group and / or an acidic group as a component of the graft copolymer, it exhibits excellent alkali developability.

[0081]

EXAMPLES The synthesis examples of the polymer of the present invention and the examples of the present invention are described below, but the present invention is not limited to these synthetic examples and examples.

[Synthesis Example 1] 42 parts by mass of pyridine and 1.3 parts by mass of polyethyleneimine (molecular weight: 600) were introduced into a three-necked flask, and stirred with a three-one motor at 80 ° C.
Temperature. Polymethyl methacrylate having a methacryloyl group at one end (AA-6; Toagosei Chemical Co., Ltd.)
27.0 parts by mass), and the mixture was stirred for 1 hour under a nitrogen stream.
Heat at 00 ° C. for 12 hours. After completion of the reaction, the solution in the flask was cooled to room temperature and reprecipitated in 500 parts by mass of methanol to obtain 24 parts by mass of a white powder. The yield was 85%. The number average molecular weight (Mn) of the selected polymer in terms of polystyrene was 7,000.

[Synthesis Example 2] The polyethyleneimine (molecular weight 6)
00) is replaced with polyethyleneimine (molecular weight 180
Except that the composition was changed to 0), 25 parts by mass of white powder was obtained in the same manner as in [Synthesis Example 1]. The yield was 88%. Number average molecular weight (Mn) of the obtained polymer in terms of polystyrene
Was 7,000.

[Synthesis Example 3] Polyethyleneimine (molecular weight 6)
00) is replaced with polyethyleneimine (molecular weight 1000
Except that the composition was changed to 0), 25 parts by mass of white powder was obtained in the same manner as in [Synthesis Example 1]. The yield was 88%. Number average molecular weight (Mn) of the obtained polymer in terms of polystyrene
Was 7,000.

[Synthesis Example 4] Polyethyleneimine (molecular weight 6)
00) is polyallylamine (molecular weight 5000)
In the same manner as in [Synthesis Example 1] except that the composition was changed to 23, 23 parts by mass of a white powder was obtained. The yield was 81%. The number average molecular weight (Mn) of the obtained polymer in terms of polystyrene is 7
000.

[Synthesis Example 5] In [Synthesis Example 1], polyethyleneimine (molecular weight 6)
00) is replaced with polyvinylamine (molecular weight 1000).
Except that the composition was changed to 0), 25 parts by mass of white powder was obtained in the same manner as in [Synthesis Example 1]. The yield was 88%. Number average molecular weight (Mn) of the obtained polymer in terms of polystyrene
Was 7,000.

Example 1 A red pigment dispersion composition having the following composition was prepared.・ C. I. Pigment Red 254 8.28 parts by mass-2.48 parts by mass of polymer of Synthesis Example 1-69.24 parts by mass of 1-methoxy-2-propyl acetate

The red pigment composition having the above composition was dispersed in a motor mill M50 (manufactured by Eiger) using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m / s for 9 hours. Was prepared.

The following evaluation was performed on the obtained pigment dispersion composition. (1) Viscosity measurement: For the obtained pigment dispersion composition,
The viscosity was measured using a type viscometer, and the degree of thickening was evaluated. The results are shown in Table 1. Here, a low viscosity indicates that the dispersion stability and fluidity are stable and good.

(2) Contrast measurement: The obtained pigment dispersion composition was applied on a glass substrate so as to have a thickness of 6 μm to prepare a sample. This sample was placed between two polarizing plates, the amount of transmitted light when the polarization axis was parallel and when the polarization axis was perpendicular was measured, and the ratio was defined as the contrast (“19”).
1990 7th Color Optics Conference, 512 color display 1
0.4 "Color filter for TFT-LCD, Ueki, Koseki, Fukunaga, Yamanaka"). The results are shown in Table 1. Here, a high contrast indicates that the fineness is high and the transmittance, that is, the coloring power is high.

Example 2 A red pigment dispersion composition was prepared in the same manner as in Example 1, except that the polymer of Synthesis Example 1 was replaced by the polymer of Synthesis Example 2. The same evaluation as in Example 1 was performed.

Example 3 A red pigment dispersion composition was prepared in the same manner as in Example 1, except that the polymer of Synthesis Example 1 was replaced with the polymer of Synthesis Example 3. The same evaluation as in Example 1 was performed.

Example 4 A red pigment dispersion composition was prepared in the same manner as in Example 1 except that the polymer of Synthesis Example 1 was replaced by the polymer of Synthesis Example 4. The same evaluation as in Example 1 was performed.

Example 5 A red pigment dispersion composition was prepared in the same manner as in Example 1, except that the polymer of Synthesis Example 1 was replaced by the polymer of Synthesis Example 5. The same evaluation as in Example 1 was performed.

Example 6 A green pigment dispersion composition was prepared in the same manner as in Example 1 except that the red pigment dispersion composition was replaced with a green pigment dispersion composition having the following composition. Then, the same evaluation as in Example 1 was performed.・ C. I. Pigment Green 36 9.20 parts by mass I. Pigment Yellow 138 4.96 parts by mass-Polymer of Synthesis Example 1 4.25 parts by mass-1-methoxy-2-propyl acetate 55.93 parts by mass

Comparative Example 1 A red pigment dispersion was obtained in the same manner as in Example 1 except that polyethyleneimine (number average molecular weight: 20,000) was used instead of the polymer of Synthesis Example 1 described above. A composition was prepared and evaluated in the same manner as in Example 1.

Comparative Example 2 A red pigment was prepared in the same manner as in Example 1 except that polymethyl methacrylate (number average molecular weight: 6000) was used instead of the polymer of Synthesis Example 1 described above. A dispersion composition was prepared and evaluated in the same manner as in Example 1.

Comparative Example 3 In Example 1, polyethyleneimine (having a molecular weight of 6) was used instead of the polymer of Synthesis Example 1 described above.
00) A graft copolymer (weight average molecular weight: 20,000) synthesized in the same manner was used except that a mixture of 0.38 part by mass and 7.90 parts by mass of polymethyl methacrylate (number average molecular weight 6000) was used. Except for the above, a red pigment dispersion composition was prepared in the same manner as in Example 1, and the same evaluation as in Example 1 was performed.

[Comparative Example 4] In Example 1, instead of the polymer of Synthesis Example 1 described above, a polymer described in Synthesis Example 1 of JP-A-10-339949 (dimethylaminoethyl acrylate and a polymer having a methacryloyl group at a terminal). Except for using a copolymer with polymethyl methacrylate), a red pigment dispersion composition was prepared in the same manner as in Example 1, and the same evaluation as in Example 1 was performed. A graft copolymer was obtained in the same manner as in Synthesis Example 1 except that the following monomer solution was used.

Example 7 The following compositions were mixed to prepare a colored photosensitive composition for producing a color filter. -32.4 parts by mass of the red pigment dispersion composition of Example 1-9.0 parts by mass of methacrylic acid / benzyl methacrylate polymer (molar ratio: 28/72, weight average molecular weight: 30,000, 30% by mass-1-methoxy) 4- [p- (N, N-bis (ethoxycarbonylmethyl) amino) -bromophenyl] -2,6-bis (trichloromethyl) -s-triazine] 0.2 mass Parts-dipentaerythritol hexaacrylate (DPHA) 2.2 parts by mass-hydroquinone monomethyl ether 0.01 parts by mass-1-methoxy-2-propyl acetate 62 parts by mass

The mixing was carried out for 9 hours at a peripheral speed of 9 m / s using a zirconia bead having a diameter of 0.65 mm with a motor mill M50 (manufactured by Eiger).

The viscosity of the obtained colored photosensitive composition for producing a color filter was measured in the same manner as in Example 1, a color filter was produced as described below, and the contrast was increased in the same manner as in Example 1. It was measured. The time required for development was measured. That is, the colored photosensitive composition for producing a color filter was applied on a glass substrate using a spin coater, and dried at 100 ° C. for 2 minutes to form a film having a thickness of about 2 μm. Next, after exposure with a super-high pressure mercury lamp under a nitrogen stream, development was carried out with a 1% aqueous solution of sodium carbonate. Further, the development time required until the film disappeared was measured. Here, the development time is short (4
0 seconds or less) indicates that the composition has excellent alkali developability. Table 1 shows the evaluation of alkali developability according to the following criteria.

[Criterion] A: Time required for development is 40 seconds or less. X: Time required for development is 50 seconds or more.

Example 8 The procedure of Example 7 was repeated, except that the red pigment dispersion composition of Example 1 was replaced by the red pigment dispersion composition of Example 2. A water-soluble composition was prepared and evaluated in the same manner as in Example 7.

Example 9 The procedure of Example 7 was repeated, except that the red pigment dispersion composition of Example 1 was replaced with the red pigment dispersion composition of Example 3. A water-soluble composition was prepared and evaluated in the same manner as in Example 7.

[Embodiment 10] In Embodiment 7, Embodiment 1 will be described.
A colored photosensitive composition was prepared in the same manner as in Example 7, except that the red pigment dispersion composition of Example 4 was replaced with the red pigment dispersion composition of Example 4, and evaluated in the same manner as in Example 7. .

[Embodiment 11] In Embodiment 7, Embodiment 1
A colored photosensitive composition was prepared in the same manner as in Example 7 except that the red pigment dispersion composition of Example 5 was replaced with the red pigment dispersion composition of Example 5, and evaluated in the same manner as in Example 7. .

[Embodiment 12] In Embodiment 7, Embodiment 1 will be described.
A colored photosensitive composition was prepared in the same manner as in Example 7, except that the red pigment dispersion composition of Example 6 was replaced with the green pigment dispersion composition of Example 6, and evaluated in the same manner as in Example 9. .

Comparative Example 5 The procedure of Example 9 was repeated, except that the red pigment dispersion composition of Example 1 was replaced by the red pigment dispersion composition of Comparative Example 4. A water-soluble composition was prepared and evaluated in the same manner as in Example 9.

[0110]

[Table 1]

From the results shown in Table 1, it can be seen that the pigment dispersion composition containing the polymer of the present invention has the same or higher dispersibility, fluidity, and tinting strength as those of the comparative example. This shows that the coloring photosensitive composition used has coloring power equal to or higher than that of the comparative example and high alkali developability. On the other hand, the same results are obtained by comparing the pigment dispersion composition of the comparative example and the colored photosensitive composition with the pigment dispersion composition containing the polymer of the present invention and the colored photosensitive composition using the pigment dispersion composition. Although some compositions exhibit dispersibility, fluidity, and coloring power, they also show low alkali developability.

[0112]

According to the present invention, the above-mentioned conventional problems can be solved. Further, according to the present invention, it is possible to provide a novel polymer which realizes stable and good dispersibility and fluidity of the pigment without aggregating the pigment and also has excellent light transmittance. Further, according to the present invention, a pigment containing the polymer, having excellent dispersibility and fluidity of the pigment, and having high coloring power, can be suitably used in a wide range of paints, printing inks, color display boards and the like. A dispersion composition can be provided. Further, according to the present invention, the pigment dispersion composition is contained, the coloring power is high, the alkali developability is excellent, the formation of a multicolor image on a substrate such as a color proof, and the color used for a liquid crystal color display and the like. It is possible to provide a colored photosensitive composition that can be suitably used for production of a filter and the like.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) G03F 7/004 505 G03F 7/004 505 F term (Reference) 2H025 AA00 AB09 AB13 AC01 AD01 BC42 CA01 CA14 CA28 CC12 CC20 FA03 FA17 2H048 BA45 BA47 BA48 BB42 4J031 AA20 AA22 AA25 AB01 AC01 AD01 AF22 4J037 AA30 CB01 CB04 CB07 CB10 CC18 EE28 EE43 FF03 FF15

Claims (5)

[Claims] 1. A graft polymer produced by an addition reaction between a polymer having a repeating unit having a primary or secondary amino group and a polymer having an ethylenically unsaturated double bond at one end. 2. The graft according to claim 1, wherein the terminal group of the polymer having an ethylenically unsaturated double bond at one terminal is selected from an acryloyl group, a methacryloyl group, an acrylamide group and a methacrylamide group. Type polymer. 3. The polymer according to claim 1, wherein the polymer having a repeating unit having a primary or secondary amino group is selected from polyethyleneimine, polyvinylamine, and a polymer having a polyallylamine unit. Graft polymer. 4. An organic solvent and an organic pigment in an organic solvent.
A pigment dispersion composition obtained by dispersing the graft polymer described in 1. above. 5. The pigment dispersion composition according to claim 4, a binder polymer having an acidic group, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. Colored photosensitive composition.