KR20060111415A - Process for the production of pigment composition, colored composition for color filter obtained by said process, and color filter - Google Patents

Abstract

Provided are a method for preparing a pigment composition, which enables a proper amount of a pigment composition to be timely produced and is small in quality deviation of products in lots, and a colored composition obtained thereby, which forms a color filter having a high contrast ratio. The method for preparing a pigment composition comprises a step of kneading a mixture including an organic pigment, water-soluble inorganic salts, water-soluble organic liquid, and a resin using a continuous kneader(10). The kneader(10) comprises a driving shaft(121), an annular fixed disc(21), a rotary disc(23) that has the same center with the fixed disc(21) and rotates around the driving shaft(121) integrally, and a dedifferentiated space formed in a gap between the fixed disc(21) and the rotary disc(23). The resin is a rosin resin.

Description

The pigment composition manufacturing method, the coloring composition for color filters obtained by the said method, and a color filter TECHNICAL FIELD

1 is a side cross-sectional view showing one embodiment of a continuous kneader used in the present invention.

2 shows a front view and a rear view of a fixed disk and a rotary disk of one embodiment employed in the continuous kneader shown in FIG. In FIG. 2, (a) is a cavity-sector-shaped fixed disk, (b) is a cavity-sector-shaped rotary disk, and (c) is a cavity-rose-shaped -shaped fixed disk, (d) cavity-rose-shaped rotary disk, (e) cavity-mortar-shaped fixed disk, and (f) cavity-mortar-shaped It is a rotary disk.

The present invention provides a method for producing a pigment composition having a remarkably excellent dispersibility in a colorant whose size is controlled to fine and uniform particle diameters, and for color filters using the pigment composition. It relates to a colored composition and a color filter using the colored composition. Specifically, a pigment composition that provides a coated material having good gloss and high dye strength when the particles of the developing powder are dispersed in a colorant of an ink or coating, such as a gravure ink or an offset ink. It relates to a method for the preparation of. The invention also relates to colored compositions for color filters used to produce color filters for use in color liquid crystal display devices and color camera tube components, and color filters formed by using the colored compositions. .

Some organic pigments, such as azo pigments, may have fine and uniform particles by selecting appropriate reaction conditions in the synthesis. With respect to some other organic pigments, such as polyhalogenated copper phthalocyanine pigments, the extremely fine and aggregated particles produced during synthesis can grow in size and become homogenous in subsequent processes. With respect to some other organic pigments, such as copper phthalocyanine pigments, a treatment called pigmentation is carried out in which coarse and non-uniform particles formed during synthesis are finely separated and uniform in size in a later process.

For example, copper phthalocyanine pigments have been used in large quantities in the coloring materials industry because they have a beautiful color tone and high tinting strength, and have various physical properties such as weather resistance and heat resistance. .

Generally, copper phthalocyanine pigments are phthalic anhydrides in organic solvents such as alkylbenzene, trichlorobenzene or nitrobenzene in the presence or absence of a catalyst such as ammonium molybdate or titanium tetrachloride under atmospheric or increased pressure. It is prepared by reaction between its derivatives, urea and a copper source or between phthalodinitrile or its derivatives and a copper source.

However, the synthesized molecule of phthalocyanine undergoes continuous particle growth in its synthetic solvent so that only coarse and acicular particles having a major axis diameter of about 10 to 200 μm can be obtained. Therefore, its value as a colored pigment for inks, coatings, plastics, etc. is very low, and such phthalocyanine is called crude copper phthalocyanine. Therefore, it is required to finely divide the crude copper phthalocyanine in order to obtain particles having high practicality in terms of coloring, that is, particles having a particle diameter of about 0.01 to 0.5 mu m.

As an industrial method for finely separating the crude copper phthalocyanine, various methods are known. For example, a small amount of solvent, such as diethylene glycol, is added to the mixture of crude copper phthalocyanine and sodium chloride and the wet mixture is kneaded vigorously with a ball mill, attritor, or batch kneader. Wet grinding is known as the so-called solvent salt milling method (see JP-A-7-53889 and JP-A-5-43704). In this method, the sodium chloride and diethylene glycol are washed with water and then dried to remove from the kneaded mixture to obtain copper phthalocyanine having fine primary particles.

However, conventional batch kneaders limit production scale due to their batch type form, lot-to-lot quality variation, incorporation of foreign materials due to their open structure, and contamination of the working environment due to the generation of powder dust I have the same problem. In addition, a large amount of energy is required to finely separate the organic pigment, and there is also a limit to the degree of fine separation. In addition, when the obtained copper phthalocyanine pigment is dispersed and used in the printing agent of the printing ink or coating such as gravure ink or offset ink, it is always desired to improve the gloss and dyeing strength of the coated material.

In the liquid crystal display device, a liquid crystal layer sandwiched between two polarizing plates adjusts the degree of polarization of light passing through the first polarizing plate and adjusts the amount of light passing through the second polarizing plate, thereby making the display. The dominant liquid crystal display device is a display device that uses a liquid crystal of twisted nematic (TN) type. The liquid crystal display device enables color display by providing a color filter between two light plates. In recent years, liquid crystal display devices have been used for television and personal computer monitors. For this reason, color filters having high brightness and high contrast are increasingly required.

A color filter consists of at least two different types of fine stripe filter segments of different shades arranged parallel or intersecting with respect to one another on a transparent substrate such as a glass substrate or fine filter segments arranged horizontally and vertically in a certain order. do. The filter segments are fine, i.e. on the order of several microns to several hundred microns, and the filter segments are systematically aligned in a predetermined arrangement by all the tones.

In a color liquid crystal display device, in general, a transparent electrode for driving a liquid crystal is formed on a filter by vacuum evaporation or sputtering, and an alignment film for aligning the liquid crystal in a predetermined direction is formed thereon. In order to fully exhibit the performance of a transparent electrode and an oriented film, it is generally required to form a transparent electrode and an oriented film at high temperature 200 degreeC or more, Preferably it is 230 degreeC or more. Recently, therefore, as a method called a pigment dispersion method, the use of a pigment excellent in light resistance and heat resistance as a colorant has been mainly adopted as a method for producing a color filter.

In general, however, color filters having pigments dispersed therein have a problem in that scattering of light due to the pigments disturbs the degree of polarization controlled by the liquid crystal. That is, light leaks when light is to be blocked (OFF state), and light that is transmitted is weakened when light must pass (ON state). There is a problem that the luminance ratio (contrast ratio) on the display device between the ON state and the OFF state is low.

In order to realize a high contrast color filter, the pigment contained in the filter segment is subjected to finely dividing treatment. As a method for finely separating a pigment, the solvent salt milling method mentioned above is widely used in recent years.

Solvent salt milling is used to finely coarse pigment particles by mechanically polishing the particles with a kneader in the presence of an inorganic salt such as sodium chloride or sodium sulfate and a water-soluble organic solvent having a high viscosity such as ethylene glycol, diethylene glycol or polyethylene glycol. It is a method of separation. Solvent salt milling methods are effective for finely separating and homogenizing pigment particles. However, in order to realize that the contrast of a color filter is improved, it is required to use the pigment which is smaller in size and has more uniform particle | grains than the pigment particle obtained by the conventional salt milling method.

A method for preparing pigment compositions that overcomes the problems of conventional batch kneaders such as production scale limitations, lot-to-lot quality variation, incorporation of foreign materials due to open structures, and contamination of the work environment due to the generation of powder dust. It is an object of the present invention to provide.

When the pigment is dispersed in a printing ink such as gravure ink or offset ink, or in a coating agent of the coating, it can impart good gloss and enhanced dye strength to the pigment coated material, and finer pigment particles such as inkjet printing or color filters are required. It is another object of the present invention to provide a process for producing pigment compositions having finer particles with smaller amounts of energy compared to conventional batch kneaders, which can also give good physical properties even in the field of application.

As a method for effectively producing fine pigments in a short time, it is another specific object of the present invention to provide a method in which the pigment cannot be obtained by a conventional batch kneader.

It is yet another object of the present invention to provide a colored composition for a color filter, which is capable of forming a color filter comprising fine and uniform particles and having a high contrast ratio.

It is yet another object of the present invention to provide a color filter having a high contrast ratio by using the colored composition.

According to the first aspect of the present invention, there is provided a method for the preparation of a pigment composition, which method comprises a drive shaft, an annular fixed disc, comprising a mixture comprising an organic pigment, a water soluble inorganic salt, a water soluble inorganic liquid and a resin. ), A method comprising kneading with a continuous kneader comprising a rotary disk concentric with the fixed disk and integrally rotating about an axis of the drive shaft and an undifferentiated space formed in a gap between the fixed disk and the rotary disk. This is provided.

According to the present invention 2, there is provided a method for the preparation of a pigment composition, each method having at least one substituent selected from the group consisting of a phthalimidomethyl group, an amino group, a sulfonic acid group and a carboxylic acid group A mixture comprising an organic dye derivative, an anthraquinone derivative or a triazine derivative, an organic pigment, a water soluble inorganic salt, and a water soluble organic liquid is driven by the drive shaft, annular fixed disc, concentric with the fixed disc. A method is provided comprising kneading with a continuous kneader comprising a rotary disk integrally rotating around an axis of a shaft and an undifferentiated space formed in the gap between the fixed disk and the rotary disk.

According to the invention 3, there is provided a colored composition for a color filter comprising a pigment carrier consisting of a transparent resin, a precursor or mixture thereof, and a pigment, wherein the pigment is an organic pigment, a water soluble inorganic salt and a water soluble The mixture comprising the organic liquid may comprise a drive shaft, an annular fixed disc, a rotary disk concentric with the fixed disk and integrally rotating about an axis of the drive shaft and the fixed disk and the rotary Fine organic pigments obtained by kneading with a continuous kneader comprising undifferentiated spaces formed in the gaps between the discs.

The present invention further provides a color filter comprising a filter segment formed of the colored composition.

First, the continuous kneader used in the present invention will be described with reference to FIG. Figure 1 is a side cross-sectional view showing an embodiment of a continuous kneader used in the present invention. As a preferable example of the continuous kneader used in the present invention, the continuous kneader described in JP-B-2-92 can be used. For example, it is preferable that the continuous kneader 10 ("Miracle K.C.K") supplied by Asada Iron Works is used.

As shown in FIG. 1, the continuous kneader 10 includes a feeding section 1, a kneading section 2, a discharge section 3 and a feeder metering feeder section. Have (4) The supply part 1 includes a cylindrical case 11 extending in the horizontal direction and a spiral rod 12 concentric with the case 11 and fitted in a sliding contact state. The raw material injection port 111 which takes raw materials from the feeder metering part 4 is open at the upper surface of the upstream casing 11. The starting end (right side of FIG. 1) of the helical rod 12 is fixed concentrically over the drive shaft 121 of the drive motor, not shown in FIG. 1, and the helical rod 12 is driven by driving the drive motor. The drive shaft 121 is rotated through the drive shaft 121. A spiral fin 122 formed in a predetermined direction is provided on the outer surface of the spiral rod 12. The raw material supplied from the feeder metering section 4 is forcibly supplied to the kneading section 2 by the rotation of the spiral plate 122 around the shaft.

The feeder metering section 4 is a raw material that will undergo a continuous kneading process (hereafter referred to as dough composition in the present invention, organic pigments, water soluble inorganic salts, water soluble organic liquids and resins or organic dye derivatives, anthraquinone derivatives or triazine derivatives) Sol or gel mixture) is provided to supply to the supply (1). The feeder metering section 4 includes a case to surround the raw material, the spiral feeder 42 for supplying the raw material from the bottom of the raw material hopper 41 to the feeder 1, and the downstream end of the cylindrical feeder 42. The raw material hopper 41 which receives the connection cylindrical body 43 provided perpendicularly from the periphery of the raw material injection hole 111 in 11 is included.

The spiral feeder 42 is mounted such that its spiral plate is in sliding contact with the intermediate cylindrical body 44 provided between the bottom hole of the raw material hopper 41 and the upper hole of the connecting cylindrical body 43. The starting end (right side in FIG. 1) of the spiral feeder 42 is concentrically connected to the drive shaft of the feed motor omitted in FIG. 1. Therefore, the raw material in the raw material hopper 41 is rotated through the intermediate cylindrical body 44 and the connecting cylindrical body 43 by the spiral feeder 42 rotating around the axis due to the driving of the feeding motor. ) Is transported into the case 11 by a predetermined transport amount.

The kneading portion 2 is a plurality of fixed disk 21, the annular dough cylinder 22 provided between the fixed disk 21 (the fixed disk 21 and the annular dough cylinder 22 are alternately arranged) ) And its front and rear surfaces (right and left sides in FIG. 1) opposing the fixed disks 21 and comprise a rotary disk 23 concentrically fitted to the cylinders 22. A tie rod, not shown in FIG. 1, is fitted through the plurality of fixed disks 21 and the kneading cylinder 22. The starting end of the tie rod is fixed to the case 11 of the supply part 1. Thus, the fixed disk 21 and the kneading cylinder 22 are integrated with the supply part 1.

Each rotary disk 23 fits into a spline shaft, not shown in FIG. 1, which projects concentrically from the foremost face of the helical rod 12. Cylindrical intermediate screws 24 are provided between each two adjacent rotary disks 23. Thus, the rotary disk 23 and the screw 24 are alternately installed on the spline shaft. The outer diameter of the rotary disk 23 is slightly smaller than the inner diameter of the kneading cylinder 22, and the outer diameter of the intermediate screw 24 is slightly smaller than the inner diameter of the fixed disk 21. Due to this, the outer circumferential surface of each rotary disk 23 and each intermediate screw 24 is kneaded through an interval through which raw materials can pass while the rotary disk 23 and intermediate screw 24 are alternately fitted to the spline shaft. The inner peripheral surfaces of the cylinder 22 and the fixed disk 21 are respectively opposed.

Due to the above construction of the continuous kneader 10, the raw material loaded into the raw material hopper 41 is drawn out from the bottom of the raw material hopper 41 by driving the spiral feeder 42, and then connected with the intermediate cylindrical body 44. It is introduced into the case 11 of the supply part 1 through the cylindrical body 43. The raw materials introduced into the case 11 are sequentially transferred to the kneading portion 2 on the downstream side by the rotation of the spiral plate 122 by driving the rotation of the spiral rod 12.

Thereafter, the raw material transferred to the kneading part 2 is first of the outer circumferential surface of the intermediate screw 24 rotating around the shaft on the most upstream side (right side in FIG. 1) and the inner circumferential surface of the fixed disk 21 on the most upstream side. Pass through the gap between. The raw material then passes through the gap between the right side of FIG. 1 of the fixed disk 21 on the most upstream side and the right side of the rotary disk 23 rotating around the axis on the most upstream side. The raw material is kneaded as it passes through these gaps. The kneading operation for the raw materials is repeated in a plurality of steps depending on the number of the fixed disk 21, the kneading cylinder 22, the rotary disk 23 and the intermediate screw 24 installed. For this reason, the plural kinds of components (organic pigments, water-soluble inorganic salts and water-soluble organic liquids and resins or organic dye derivatives, anthraquinone derivatives or triazine derivatives) of the raw materials undergo kneading treatment. The product obtained by the completion of the kneading treatment is discharged from the interval, that is, from the discharge section 3, between the outer circumferential surface of the rotary disk 23 located on the downstream side and the dough cylinder 22 located on the downstream side. .

FIG. 2 shows a front view (as seen from the right side of FIG. 1) or a back view (as seen from the left side of FIG. 1) of the fixed disk and the rotary disk used in one embodiment of the continuous dough shown in FIG. 1. In Fig. 2, (a) is a cavity-sector-shaped fixed disk 21a, (b) is a cavity-sector-shaped rotary disk 23b, and (c) is a cavity-rose-shaped (cavity-rose). -shaped fixed disks 21c, (d) are cavity-rose-shaped rotary disks 23d, (e) are cavity-mortar-shaped fixed disks 21e, and ( f) is a cavity-mortar-shaped rotary disk 23f.

As shown in FIG. 2, each fixing disk 21 has a loose fixing hole 211 in which the intermediate screw 24 is loosely fixed and concentric with the intermediate screw 24. A plurality of recesses (cavities (pulverizing spaces) 212) are radially from the loose fixing holes 211 in front and rear surfaces (front side and back side) of each fixing disk 21. It is recessed in phase and these recesses are provided to a regular degree in the circumferential direction. On the other hand, each rotary disk 23 has a fixing hole 231 concentric with the spline shaft to be fixed in a state where the spline shaft omitted in FIG. 1 is in close contact. A cavity (undifferentiated space) 232 corresponding to the cavity 212 of the fixed disk 21 is dug on the front and rear surfaces of each rotary disk 23. The margin of each cavity 232 of the rotary disk 23 is open.

The raw material introduced at the interval between the fixed disk 21 and the rotary disk 23 is pushed into the respective cavities 212 and 232 as a result of the driving of the spiral rod 12. The rotation of the rotary disk around the axis in this state exerts shear forces on the raw materials in the cavities 212 and 232 at the interface between the cavities 212 and 232. That is, the raw materials in the cavity 212 of the fixed disk 21 and the cavity 232 of the rotary disk 23 which are opposed to each other are cavities 212 and 232 such that shear forces and substitutes act on the raw materials. It is cut by the bumps of the site, whereby the raw material is kneaded and dispersed. In this alternative, the sheared raw material is present in the cavities 212 and 232 and the new raw material enters the same cavities 212 and 232.

The fixed disk 21 and the rotary disk 23 are classified into a plurality of different types of fixed disks and rotary disks according to the shapes of the cavities 212 and 232. That is, they are a cavity-sector-shaped fixed disk 21a and a cavity-sector-shaped rotary disk 23b shown in (a) and (b) in FIG. 2 and (c) and (d) in FIG. Cavity-rose-shaped fixed disk 21c and cavity-rose-shaped rotary disk 23d shown by and cavity-mortar-shaped fixed shown by (e) and (f) in FIG. Disk 21e and cavity-mortar-type rotary disk 23f. These different kinds of stationary disks and rotary disks are used to increase the shear force acting on the raw material as the dough and dispersion processes proceed.

That is, from the highest to the lowest porosity grading of the cavities 212 and 232 (cavity of the fixed disk 21 or cavity of the rotary disk 23 based on the surface area of the fixed disk 21 or the rotary disk 23). Percent of the area of s are the sector-shaped cavity 212 or 232, the rose-shaped cavity 212 or 232, and the mortar-shaped cavity 212 or 232.

In this embodiment, the fixed disk 21 having the sector-shaped cavity 212 and the rotary disk 23 having the sector-shaped cavity 232; A fixed disk 21 having a rose-shaped cavity 212 and a rotary disk 23 having a rose-shaped cavity 232; And the shear force acting on the raw materials of the fixed disk 21 having the mortar-type cavity 212 and the rotary disk 23 having the mortar-type cavity 232 increases with the progress of kneading and dispersion processing of the raw material. So as to be sequentially arranged from the upstream side to the downstream side.

In this method, a large shear force is not suddenly applied to the raw material, but as the kneading and dispersion processing of the raw material proceeds, the shear force acting on the raw material increases sequentially. Therefore, the kneading and dispersing treatment is smoothly provided to the raw materials without any extra resin. Therefore, organic pigments, water-soluble inorganic salts, water-soluble organic liquids and resins or organic dye derivatives, anthraquinone derivatives or triazine derivatives, which are components of the raw materials, respectively, can be mixed and dispersed with one another without fail.

According to the continuous kneader 10 having such a structure, when the organic pigment as a component of the raw material is composed of coarse particles, the organic pigment of the coarse particles fixes the organic pigment to the fixed disk 21 and the rotary disk 23. It can be separated into fine particles by impregnating organic pigments into the gaps between them (especially the cavities 212 and 213) and applying shear force to the coarse particles by rotation of the rotary disk 23.

In another aspect, when the organic pigment consists of agglomerates of fine particles, these aggregates are introduced into the gap between the fixed disk 21 and the rotary disk 23 (in particular, the cavity 212 and 232) and the rotary disk. By rotating (23), these agglomerates can be crushed and uniformized.

The pigment to be kneaded and dispersed with the continuous kneader 10 will be described in detail below. The pigment composition of the present invention 1 comprises a mixture comprising an organic pigment, a water soluble inorganic salt, a water soluble organic liquid and a resin concentric with the drive shaft 121, the annular fixed disk 21, the fixed disk 21 and the drive shaft. Obtained by kneading with a continuous kneader 10 comprising a rotary disk 23 integrally rotating about an axis of 121 and an undifferentiated space formed in the gap between the fixed disk 21 and the rotary disk 23. Lose.

The organic pigments used in the present invention include organic pigments such as azo pigments in which particles are made fine and uniform in size by selecting appropriate reaction conditions in the synthesis; Organic pigments such as polyhalogenated copper phthalocyanine pigments in which the particles can be uniform in size after growth of the aggregated extremely fine particles produced in the synthesis; And organic pigments such as copper phthalocyanine pigments in which coarse and non-uniform particles produced during synthesis can be uniform in size by finely separating the particles in a later step. In addition, the organic pigment is not particularly limited as long as it is a pigment that needs to be finely separated and uniform in size. The organic pigment can be selected from organic pigments known in the art. Examples of the organic pigments include azo pigments, phthalocyanine pigments and quinacridone pigments, and areoindolinone, isoindolin, perylene, perinone, and dike Topyrrolopyrrole (diketopyrrolopyrrole), thioindigo (dioindigo), dioxazine (dioxazine), quinophthalone (quinophthalone), anthraquinone (indhraquinone) and indanthrone (indanthrone) is further included. It is possible to finely separate a mixture of at least two organic pigments.

The water-soluble inorganic salt used in the present invention is not particularly limited. Examples thereof include salt (sodium chloride), potassium chloride, sodium sulfate, zinc chloride, calcium chloride, and mixtures thereof.

The water-soluble organic liquid used in the present invention is added to form a homogeneous dough of organic pigments and water-soluble inorganic salts. The water-soluble organic liquid is not particularly limited as long as it has a solubility that can be freely mixed with water or cannot be freely mixed with water, as long as it has a solubility that can be industrially removed by washing with water, which allows the pigment particles to grow. As the temperature rises during kneading, the liquid can easily evaporate. For this reason, solvents having a high boiling point are preferable in terms of stability. Examples thereof include 2- (methoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol Monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene Glycol monomethyl ether, dipropylene glycol monoethyl ether, low molecular weight polypropylene glycol, aniline, pyridine, tetra hydrofuran, dioxane, methanol, ethanol, isopropanol, n-propanol, isobutanol, n-butanol, ethylene glycol, Propylene glycol, propylene glycol monomethyl ether acetate, ethyl acetate, isopropyl acetate, acetone, methyl ethyl ketone, dimethylformami , It includes dimethylsulfoxide and N- methylpyrrolidone.

Mixtures of at least two organic liquids may be used as needed.

The resin used in the present invention is preferably a resin which hardly dissolves in water, is a liquid or a solid at room temperature, and particularly a resin which is soluble in the water-soluble organic liquid used in the present invention.

Examples of these include rosin, disproportionated rosin, polymerized rosin, hydrogenated rosin, rosin esters, rosin amines, maleic acid-modified rosin, fumaric acid-modified rosin Rosin resins, such as rosin metal salts, rosin-modified phenolic resins and rosin-modified maleic acid resins, epoxy resins, acrylic resins, maleic acid resins, butyral resins, polyester resins, melamine resins, phenolic resins Synthetic resins such as polyurethane resins and polyamide resins, and modified resins derived from cellulose, rubber and the like. In particular, the rosin resin is preferable in terms of addition and price.

The amount of the water-soluble inorganic salt in the kneading composition of the present invention is not particularly limited. The amount of water-soluble inorganic salt is preferably 0.5-30 times the amount of organic pigment by weight. If less than 0.5 times by weight, it is difficult to finely-dividing (hereinafter referred to as 'derivation'). If it is more than 30 times by weight, finely-divided pigments may be obtained, but this is not industrially desirable since the amount of pigments to be processed is reduced and productivity is reduced. .

The amount of the water-soluble organic liquid in the dough composition of the present invention is not particularly limited. Preferably it is 0.01-0.5 times the total amount of organic pigment and water-soluble inorganic salt by weight. When it is less than 0.01 times by weight, the dough composition becomes too hard and stable work is difficult. If the weight is more than 0.5 times, the dough composition becomes soft and the degree of fine grinding is reduced.

Moreover, the amount of the resin in the dough composition of the present invention is not particularly limited. Preferably it is 0.001-1.0 times the amount of organic pigment by weight. When the weight is smaller than 0.001 times, the effect by addition is not obtained. When it exceeds 1.0 times by weight, the effect corresponding to the amount of resin added is not obtained. Furthermore, it is preferable to adjust the amount of the resin according to the difference in properties between the resin and the vehicle resin using the obtained pigment composition. In other words, in the case of greatly different, the resin is used in the minimum amount so as to reduce the influence by the physical properties of the color resin. On the other hand, when there is little difference, it is preferable to increase the amount of resin so that the effect by this invention can fully be exhibited.

Organic pigments, water-soluble inorganic salts, water-soluble organic liquids and resins which are components of the dough composition according to the present invention 1 may be added separately to a continuous kneader at the same time. Alternatively, these components can be added to the continuous kneader after they are mixed. Moreover, a resin may be added during the production of the organic pigment to form a mixture of the organic pigment and the resin in advance. In this case, the effect of resin addition is remarkable.

The present invention relates to a method for preparing a pigment composition, which is an organic dye derivative, anthraquinone derivative or tra, each containing at least one substituent selected from the group consisting of phthalimidomethyl group, amino group, sulfonic acid group and carboxylic acid group A mixture comprising a azine derivative, an organic pigment, a water-soluble inorganic salt and a water-soluble organic liquid is a driving shaft, an annular fixed disk, the same center as the fixed disk, and is arranged around the axis of the drive shaft. Kneading with a continuous kneader comprising an integrally rotating rotary disk and a pulverizing space formed in the gap between the fixed disk and the rotary disk.

The organic dye derivative containing at least one substituent selected from the group consisting of a phthalimidomethyl group, an amino group, a sulfonic acid group and a carboxylic acid group used in the present invention 2 is typically an organic dye derivative represented by the following formula (1).

P- {X _1- (Y ₁ ) k} m (One)

In which P represents an organic dye residue; X ₁ is a single bond or -O-, -S-, -CO-, -SO _2- , NR _1- , -CONR _1- , -SO ₂ NR _1- , -NR ₁ CO- or -NR ₁ SO _2, consisting of a linear or branched alkylene group, an alkyl group, an amino group, a nitro group, a hydroxy group, an alkoxy group or a halogen atom benzene or triazine residue or at least two of these couplers which may be substituted having from 1-12 carbon atoms in combination A bonding group (combinational bonding group), wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; Y ₁ is a phthalimidomethyl group which may be substituted with a nitro group or a halogen atom, —NR ₂ R ₃ , —SO ₃ · M / n or —COO · M / n; Wherein R ₂ and R ₃ each represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or unsubstituted phenyl group, or R ₂ and R ₃ are further nitrogen Together form a substituted or non-substituted heterocyclic group which may contain atoms, oxygen atoms or sulfur atoms, M being hydrogen ions, metal ions having valences of 1-3 or ammonium ions substituted with at least one alkyl group N is the valence of M; k is an integer of 1 or 2; m is an integer of 1-4.

An anthraquinone derivative including at least one substituent selected from the group consisting of a phthalimidomethyl group, an amino group, a sulfonic acid group and a carboxylic acid group used in the present invention 2 is typically an anthraquinone derivative represented by the following formula (2).

Q- {X _2- (Y ₂ ) k} m (2)

Wherein Q represents an anthraquinone moiety which may be substituted with an alkyl group, an amino group, a nitro group, a hydroxy group, an alkoxy group or a halogen atom; X ₂ is a single bond or -O-, -S-, -CO-, -SO _2- , NR _1- , -CONR _1- , -SO ₂ NR _1- , -NR ₁ CO- or -NR ₁ SO ₂ Combined bond groups consisting of linear or branched alkylene groups, alkyl groups, amino groups, nitro groups, hydroxy groups, alkoxy groups or benzene or triazine moieties which may be substituted with 1-12 carbon atoms or at least two of these bond groups; Wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; Y ₂ is a phthalimidomethyl group which may be substituted with a nitro group or a halogen atom, —NR ₂ R ₃ , —SO ₃ · M / n or —COO · M / n; Wherein each R ₂ and R ₃ individually represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or non-substituted phenyl group or R ₂ and R ₃ are additional Together form a substituted or non-substituted heterocyclic group which may contain nitrogen, oxygen or sulfur atoms, M being hydrogen ions, metal ions having 1-3 valences or ammonium substituted with at least one alkyl group Ions, n is the valence of M; k is an integer of 1 or 2; m is an integer of 1-4.

Triazine derivatives containing at least one substituent selected from the group consisting of phthalimidomethyl groups, amino groups, sulfonic acid groups and carboxylic acid groups used in the present invention are typically triazine derivatives represented by the following formula (3).

In which R represents a triazine residue; X ₃ to X ₅ Each is independently a single bond or -O-, -S-, -CO-, -SO _2- , NR _1- , -CONR _1- , -SO ₂ NR _1- , -NR ₁ CO- or -NR ₁ SO ₂ -consisting of a linear or branched alkylene group having 1-12 carbon atoms, an alkyl group, an amino group, a nitro group, a hydroxy group, an alkoxy group or a benzene moiety which can be substituted with a halogen atom or at least two of these bonding groups A combined bonding group, wherein R ₁ represents a hydrogen atom, an alkyl group or a hydroxyalkyl group; Y ₃ is a phthalimidomethyl group which may be substituted with a nitro group or a halogen atom, —NR ₂ R ₃ , —SO ₃ · M / n or —COO · M / n; Wherein each R ₂ and R ₃ individually represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group or a substituted or non-substituted phenyl group or R ₂ and R ₃ are And together form a substituted or non-substituted heterocyclic group which may contain nitrogen, oxygen or sulfur atoms, M being hydrogen ions, metal ions having 1-3 valences or at least one alkyl group Ammonium ion, n is the valence of M; Y ₄ And Y ₅ Each independently has the same definition as in the definition for Y ₃ or represents an alkyl group, an amino group, a nitro group, a hydroxyl group, an alkoxy group, a halogen atom or a substituted or unsubstituted phenyl group; p, q, and r are each independently an integer of 1 or 2.

Examples of the organic dyes (dyestuff) constituting the organic dye derivative of formula (1) used in the present invention 2 are diketopyrrolopyrrole dyes, azo dyes such as azo dyes, diazo dyes and polyazo dyes. , Anthraquinone dyes such as phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine, flavanthrone, andanthrone, indanthrone, pyrantrone, and violatron, quinacridone dyes, and dioxazine dyes , Perinone dyes, perylene dyes, thioindigo dyes, isoindolin dyes, isoindolinone dyes, quinophthalone dyes, threne dyes, and metal complex dyes. The anthraquinone constituting the anthraquinone derivative of formula (2) may be substituted with a substituent such as an alkoxy group exemplified by an alkyl group, an amino group, a nitro group, a hydroxy group, a methoxy group or an ethoxy group, or a halogen atom exemplified by chlorine Anthraquinones that may include. The triazine constituting the triazine derivative of formula (3) is 1, 3, 5-triazine.

In the present invention 2, the organic dye derivative of formula (1), the anthraquinone derivative of formula (2) and the triazine derivative of formula (3) are organic compounds obtained by introducing specific substituents into the organic dye, anthraquinone or triazine. . Examples of the substituent include phthalimidomethyl group, 4-nitrophthalimidomethyl group, 4-chlorophthalimidomethyl group, tetrachlorophthalimidomethyl group, (4,6-bis (phthalimidomethylamino) -1,3,5- Triazine) -2-ylamino methyl group, carbamoyl group, sulfamoyl group, methylamino group, ethylamino group, propylamino group, butylamino group, hexylamino group, octylamino group, dodecylamino group, octadecylamino group, dimethylamino group, diethylamino group , Dibutylamino group, dimethyl aminopropylamino group, diethyl aminopropylamino group, diethyl aminoethyl amino group, dibutyl aminopropyl amino group, piperidinomethyl group, dimethyl aminomethyl group, diethyl aminomethyl group, dibutyl aminomethyl group, (4, 6-bis (diethylaminopropylamino) -1,3,5-triazine) -2-yl group, (4,6-bis (diethylaminopropylamino) -1,3,5-triazine) -2 -Monoamino group, (4- (diethyl Aminopropylamino) -6-hydroxy-1,3,5-triazine) -2-ylamino group, dimethylaminopropylaminosulfonyl group, diethylamino propylamino sulfonyl group, dibutylamino propylamino sulfonyl group, morpholi Noethyl amino sulfonyl group, dimethylamino propylamino carbonyl group, 4- (diethylaminopropylaminocarbonyl) phenylamino carbonyl group, dimethylamino methyl carbonyl aminomethyl group, diethylaminopropyl aminomethyl carbonyl aminomethyl group, dibutylaminopropyl Aminomethyl carbonyl aminomethyl group, sulfonic acid group, sodium sulfonate group, calcium sulfonate group, strontium sulfonate group, barium sulfonate group, aluminum sulfonate group, 4- (aluminum sulfonate) phenyl carbamoyl methyl group, dodecyl Dodecyl ammoniosulfonate group, octadecyl ammoniosulfonate group, trimethyl octa O-decyl ammonium sulfonate group, a dimethyl-dideoxy includes a chamber ammonium O-sulfonate group, a carboxylic acid group and a 2-carboxylate-5-nitrobenzamide aluminum amido group. In addition to the above substituents, with respect to the triazine derivative of formula (3), examples of further substituents include hydroxy group, amino group, methoxy group, ethoxy group, phenoxy group, 4-nitrophenylamino group, 4-benzaminophenylamino group or 4- Aminophenoxy groups.

In the present invention 2, the organic dye derivative of formula (1), the anthraquinone derivative of formula (2) and the triazine derivative of formula (3) are, for example, JP-B-39-28884, JP-A-51-18736 , JP-A-54-62227, JP-A-56-32549, JP-A-56-81371, JP-A-56-118462, JP-A-56-166266, JP-A-59-96175, JP It can be prepared by the method described in -A-60-88185, JP-A-60-98525, JP-A-63-305173, JP-A-03-26767 and JP-A-11-199796.

Specific examples of the organic dye derivative of formula (1), the anthraquinone derivative of formula (2) and the triazine derivative of formula (3) in the present invention 2 are shown below by compound number.

Organic compounds, organic pigments, water-soluble inorganic salts selected from organic dye derivatives of formula (1), anthraquinone derivatives of formula (2) and triazine derivatives of formula (3), each of which is a component of the dough composition of the present invention 2 and The water-soluble organic liquid may be added independently to the continuous kneader at the same time. Alternatively, these ingredients may be added to a continuous kneader after they have been mixed. In addition, the derivative may be added during the preparation of the organic pigment to form a mixture of the organic pigment and the derivative in advance. In this case, the effect of the derivative addition is very remarkable.

In the present invention, the operating conditions of the continuous kneader are not particularly limited. In order to control the amount of organic pigments or the quality of fine organic pigments obtained, the amount of kneading temperature and the amount of mechanical energy input (the number of revolutions of the main shaft (driving shaft 121), the amount of raw material feed, Shaft shaft power load, etc.) can be adjusted. Due to the contact between the organic pigment particles and the water-soluble organic liquid, it is possible to grind the organic pigment particles and grow the organic pigment particles and to dissolve the resin in the water-soluble organic particles, thereby adsorbing the resin onto the surface of the organic pigment. The kneading temperature is preferably 10-150 ° C, particularly preferably 40-130 ° C. The increase in the kneading temperature may promote the growth rate of the pigment particles. The amount or quality of the pigment composition can be controlled by adjusting the mixing ratio of the dough composition, the kneading temperature and the mechanical energy input amount (main shaft (rotation of the driving shaft 121), the supply amount of the raw material, the amount of power applied to the main shaft, etc.). have. When the kneading temperature is higher than 150 ° C., grain growth is remarkable, and therefore, it is required to perform the kneading in a short time. In this case, however, the time for homogenizing the particles is shortened, which is undesirable in terms of quality. After starting the dough, it can be heated or cooled as necessary. Furthermore, the raw material may be provided to the inlet at an intermediate position of the continuous kneader, and the resin may be added to the derivative or the water-soluble organic liquid during the continuous kneading step to change the mixing ratio of the dough composition. The total kneading conditions can be controlled by connecting multiple continuous kneaders in a row and by setting different operating conditions for each dough mixer.

After kneading, the pigment composition is treated in a general manner. That is, the dough composition is treated with an aqueous solution of water or inorganic acid, and then filtered and washed with water to remove the water-soluble inorganic salts and water-soluble organic liquid and to separate the pigment composition. The pigment composition may be used as it is. Moreover, the pigment composition can also be used in a powder state that can be obtained by drying and pulverizing it. Resins, surfactants and / or other additives may be added after kneading as needed.

The average primary particle diameter of the fine organic pigments depends on the finely divided treatment conditions and the type of organic pigment. The primary particle diameter can be arbitrarily adjusted in the range of about 10-500 nm by suitably setting the above conditions.

In the pigment compositions of the present invention, very fine pigment particles can be produced with less energy using certain continuous kneader means. The pigment particles are coated with the resin or the derivative by finely separating the pigment particles in the kneading step and adding the resin or the derivative at the same time so that the pigment composition is dispersed while maintaining the state of the fine pigment particles in the ink or the coating agent. The mutual aggregation of the said pigment particle is reduced.

The pigment compositions of the invention are suitable for applications in which high transparency is required. Thus, the pigment compositions of the present invention exhibit very good quality in applications such as gravure inks, inkjet inks and color filters. Moreover, it also exhibits good quality in applications such as offset inks, coatings, plastic coloring and color toners. For example, when gravure inks are produced, the vehicle used consists of a resin and a solvent. The colorant is not particularly limited and may include an auxiliary agent or extender pigment. Examples of resins include gum rosin, wood rosin, tall oil rosin, lime rosin, rosin ester, maleic acid resin, polyamide resin, vinyl resin, cellulose nitrate, cellulose acetate, Ethyl cellulose, chlorinated rubber, cyclized rubber, ethylene-vinyl acetate copolymer resins, urethane resins, polyester resins, alkyd resins, acrylic resins, gilsonite, dammar, shellac ), A resin mixture containing a resin as described above, a water-soluble resin obtained by dissolving any one of the above resin mixtures and the above resin in water, and an emulsion resin. For example, the solvent includes hydrocarbon, alcohol, ketone, ether alcohol, ether, ester and water. In particular, when cellulose type resins are used, high quality gravure inks with excellent acid transparency, high gloss and high clearance can be obtained. Moreover, the pigment composition is excellent with the colorant by using a dispersing device such as a dissolver, a high speed mixer, a homomixer, a kneader, a flusher, a roll mill, a sand mill or an attritor. Mixed or dispersed in a colorant.

The colored composition for color filters provided in the present invention 3 is a color filter coloring composition comprising a pigment carrier composed of a transparent resin, a precursor thereof or a mixture thereof, and a pigment, The pigment is A mixture comprising organic pigments, water soluble inorganic salts and water soluble organic liquids comprises a drive shaft, an annular fixed disk, a rotary disk concentric with the fixed disk and integrally rotating the drive shaft axis, and the fixed disk. And characterized in that it comprises a fine organic pigment obtained by kneading with a continuous kneader comprising a pulverizing space formed in the gap between the rotary disk.

Furthermore, the color filter of the present invention 3 is characterized in that the colored filter comprises a filter segment formed from the coloring composition of the present invention.

A mixture comprising said organic pigment, a water soluble inorganic salt and a water soluble organic liquid and optionally comprising said resin and / or pigment derivative, and further kneaded with said continuous kneader 10 (hereinafter sometimes referred to as a "kneading composition). Will be described in detail.

The organic pigment used in the present invention 3 is selected from known organic pigments used in color filters. The organic pigments may be used alone or in combination. When an organic pigment having an average primary particle diameter of 0.1-0.5 μm is used as the organic pigment, the organic pigment may be finely divided into very fine particles having an average primary particle diameter of 0.01-0.1 μm. In particular, it exhibits high contrast, and therefore it is preferred to use such organic pigments. As organic pigments, crude organic pigments which do not change in the synthesized state may also be used. That is, (a) large particles having an average primary particle diameter of about 10-200 μm or (b) very-strong aggregated particles, which are very fine particles having an average primary particle diameter of 0.01 μm or less, may be used. Can be.

Specific examples of organic pigments that can be used in the present invention 3 are shown below as color index numbers. For red colored compositions for forming red filter segments, see C.I. Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 246, 254, 255, 264 and Red pigments such as 272 can be used. In the red composition, yellow pigments and / or orange pigments may additionally be used.

The yellow composition which forms a yellow filter segment includes C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, Yellow pigments such as 181, 182, 185, 187, 188, 193, 194 and 199 can be used.

Orange pigments such as C.I. Pigment Orange 36, 43, 51, 55, 59, and 61 may be used in the orange composition forming the orange filter segment.

Green pigments such as C.I. Pigment Green 7, 10, 36, and 37 may be used in the green composition forming the green filter segment. In green compositions, yellow pigments may additionally be used.

Blue compositions that form blue filter segments include C.I. Blue pigments such as Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60 and 64 can be used. In the blue composition, C.I. Violet pigments such as Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42 and 50 can additionally be used.

Cyan compositions forming cyan color filter segments include C.I. Blue pigments such as Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16 and 81 can be used.

Magenta compositions that form magenta color filter segments include C.I. Pigment Violet 1 and 19 and C.I. Violet pigments and red pigments such as Pigment Red 144, 146, 177, 169 and 81 can be used. In the magneto composition, a yellow pigment may additionally be used.

Derivatives obtained by introducing basic or acidic substituents or phthalimidomethyl groups into organic dyes in order to prevent crystal growth or crystal conversion of organic pigments when the organic pigments, water-soluble inorganic salts and water-soluble organic liquid mixtures are kneaded. Anthraquinones, acridons or triazines may be added. In particular, it is preferable to add the pigment derivative obtained by introducing a basic or acidic substituent or a phthalimidomethyl group into an organic pigment. As the basic substituent, substituents represented by the following formulas (4) to (7) can be used. Acidic substituents are typically sulfonic acid groups or carboxy groups.

The pigment derivative having the same matrix structure as that of the finely divided organic pigment is preferably a pigment derivative. Pigment derivatives having a matrix structure different from the matrix structure of the finely divided organic pigments may also be used.

The amount of the pigment derivative per 1 part by weight of the organic pigment in the dough composition is preferably 0.001-0.3 parts by weight. When the amount of the pigment derivative is less than 0.001 parts by weight, it is difficult to obtain the effect of the addition. If it exceeds 0.3 parts by weight, the effect corresponding to the amount of addition cannot be obtained, and moreover, the obtained fine organic pigment becomes a mixture of the pigment and the pigment derivative. In this case, the physical filter and other properties of the organic pigment are increased as a single material, so that the color filter formed by using the coloring composition containing such a fine organic pigment has in some cases substantial quality problems.

In formulas (4) to (7), X represents -SO _2- , -CO-, -CH ₂ NHCOCH _2- , -CH ₂ -or a single bond; n represents an integer of 1-10; R ₁ and R ₂ each independently represent a substituted or unsubstituted alkyl group having 1-36 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 36 carbon atoms, or a substituted or unsubstituted phenyl group Or R ₁ and R ₂ form a substituted or non-substituted heterocyclic ring which may further include a nitrogen atom, an oxygen atom or a sulfur atom; R ₃ represents a substituted or unsubstituted alkyl group having 1-36 carbon atoms, a substituted or unsubstituted alkenyl group or substituted or unsubstituted phenyl group having 2-36 carbon atoms; R ₄ , R ₅ , R ₆ and R ₇ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1-36 carbon atoms, a substituted or unsubstituted alkenyl group having 2-36 carbon atoms Or substituted or non-substituted phenyl group; Y represents —NR ₈ —Z—NR ₉ — or a single bond, wherein R ₈ and R ₉ are each independently a hydrogen atom, a substituted or non-substituted alkyl group having 1-36 carbon atoms, 2-36 groups Substituted or unsubstituted alkenyl groups or substituted or unsubstituted phenyl groups having carbon atoms; Z is a substituted or unsubstituted alkylene group having 1 to 36 carbon atoms, a substituted or non-substituted alkenylene group having 2 to 36 carbon atoms, or a substituted or non- A substituted phenylene group; R is a substituent represented by formula (8)

(Wherein n, R ₁ And R ₂ is as defined above.) Or a substituent represented by formula (9)

(Wherein R ₃ to R ₇ are the same as defined above), and Q represents a hydroxy group, an alkoxy group, a substituent represented by formula (8) or a substituent represented by formula (9).

Examples of the organic pigments constituting the pigment derivative include diketopyrropyrrole pigments; Azo pigments such as azo, diazo or polyazo pigments; Phthalocyanine pigments; Anthraquinone pigments such as diaminodianthraquinone, anthrapyrimidine, flavanthrone, anthanthrone, indanthrone, pyranthrone, or bioranthrone; Quinacridone pigments; Dioxazine pigments; Perynone pigments; Perylene pigments; Thioindigo pigments; Isoindoline pigments; Isoindolinone pigments; Quinophthalone pigments; Threne pigments; And metal composite pigments. In addition, the pigments used in the kneading compositions shown above can be used.

Each of the anthraquinones and acridons constituting the anthraquinone derivatives and the acridon derivatives is an alkyl group represented by a methyl group or an ethyl group; Amino group; Nitro group; Hydroxyl group; An alkoxy group represented by a methoxy group or an ethoxy group; Or anthraquinones and acridons, which may each have respective substituents, such as halogens represented by chlorine.

Triazine constituting the triazine derivative is an alkyl group represented by a methyl group or an ethyl group; Alkylamino groups represented by amino groups or dimethylamino groups, diethylamino groups or dibutylamino groups; Nitro group; Hydroxyl group; An alkoxy group represented by a methoxy group, ethoxy group or butoxy group; Halogen represented by chlorine; Phenyl group which may be substituted by a methyl group, a methoxy group, an amino group, a dimethylamino group, or a hydroxyl group; Or 1,3,5-triazine which may have a substituent such as a phenylamino group which may be substituted with a methyl group, ethyl group, methoxy group, ethoxy group, amino group, dimethylamino group, diethylamino group, nitro group or hydroxyl group .

Each pigment derivative, anthraquinone derivative and acridon derivative with basic substituents can be synthesized through various synthetic routes. For example, they introduce a substituent represented by any one of the following formulas (10) to (13) into an organic pigment, atlaquinone or acridon, and react the substituent with an amine component that can react with the substituent. It can be obtained by forming a substituent represented by any one of formulas (4) to (7). Examples of the amine component include N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine and 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3, 5-triazin-2-ylamino] aniline.

In the reaction between the substituent represented by any one of the above formulas (10) to (13) and the amine component, a part of the substituents of any one of formulas (10) to (13) is hydrolyzed and a chlorine atom is a hydroxyl group. Substances formed by substituting may be present simultaneously. In this case, the substituent of Formula (10) becomes a sulfonic acid group, and the substituent of Formula (11) becomes a carboxylic acid group. Each of these may be free acid. In addition, each of these may be a salt having 1 to trivalent metal or the above monoamine.

When the organic pigment is an azo pigment, an azo pigment derivative having a basic group can be prepared by introducing a substituent represented by any one of formulas (4) to (7) into the diazo component or the coupling component beforehand and carrying out a coupling reaction. Can be.

Furthermore, triazine derivatives with specific basic groups can be obtained through various synthetic routes. For example, at least one chlorine of cyanuric chloride as starting raw material is used to form a substituent represented by any one of formulas (4) to (7) such as N, N-dimethylaminopropylamine or N-methylpiperazine. After reacting with the amine component, the remaining chlorine of the cyanuric chloride can be synthesized by reacting with amine, alcohol or the like.

Specific examples of the derivative having a basic substituent are shown below, but the derivative is not limited to these examples. These derivatives may be used alone or in combination.

Next, the coloring composition for color filters containing the obtained fine organic pigment and the pigment carrier provided by this invention is demonstrated.

The fine organic pigment is dispersed in the pigment carrier contained in the coloring composition of the present invention 3. The pigment carrier comprises a transparent resin, precursors thereof or mixtures thereof. The transparent resin preferably exhibits a light transmittance of 80% or more, more preferably 95% or more, with respect to the total visible light wavelength of 400-700 nm. The transparent resin includes a thermoplastic resin, a thermosetting resin and an active energy beam curable resin. The precursor includes each monomer and oligomer that is cured by active energy beam irradiation, thereby producing a transparent resin. These may be used alone or in combination.

The pigment carrier may be used in an amount of 30 to 700 parts by weight, preferably 60 to 450 parts by weight, per 100 parts by weight of the pigment in the coloring composition. When a mixture of the transparent resin and its precursor is used as the pigment carrier, the transparent resin can be used in an amount of 20 to 400 parts by weight, preferably 50 to 250 parts by weight, per 100 parts by weight of the pigment in the coloring composition. Furthermore, the transparent resin precursor may be used in the amount of 10 to 300 parts by weight, more preferably 10 to 200 parts by weight per 100 parts by weight of the pigment in the coloring composition.

Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinylchloride, vinyl chloride-vinyl acetate copolymer, polyvinylacetate, polyurethane resin, polyester resin, Acrylic resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylenes (HDPE and LDPE), polybutadienes, and polyimide resins. Examples of thermosetting resins include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins and phenolic resins.

Examples of the active energy beam curable resins include an isocyanate group, an aldehyde group or an epoxy group in a polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group, and a photocrosslinkable group such as a (meth) acryloyl group or a styryl group. Acids such as resins and styrene-maleic anhydride copolymers or α-olefin-maleic anhydride copolymers prepared by introduction of a reaction between the polymer and a (meth) acrylic compound or cinnamic acid having the same reactive substituent Linear polymers comprising anhydrides include resins prepared by semi-esterification reactions with (meth) acrylic compounds having hydroxyl groups such as hydroxyalkyl (meth) acrylates.

Examples of monomers and oligomers that are transparent resin precursors include various acrylate esters and methyl (meth) acrylates, ethyl (meth) acrylates, 2-hydroxyethyl (meth) acrylates, and 2-hydroxypropyl (meth) acrylates. , Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate , Tripropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, 1,6-hexanediol diglycidyl ether di (meth) acrylate, bisphenol A Diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate , Tricyclodecanyl (meth) methacrylate ester such as acrylate, polyester acrylate, methyl Olay suited melamine (meth) acrylate, epoxy (meth) acrylate, and urethane acrylate; (Meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-vinyl formamide And acrylonitrile. These may be used alone or in combination.

A photoinitiator etc. are added to the coloring composition for color filters of this invention 3 when a coloring composition hardens | cures by ultraviolet irradiation.

Examples of the photoinitiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1 -One), 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one and 2-methyl-1- [4- ( Acetophenone photopolymerization initiators such as methylthio) phenyl] -2-morpholinopropan-1-one; Benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzyl dimethyl ketal; Benzophenone photopolymerization initiators such as benzophenone, benzoylbenzoic acid, methyl benzoyl benzate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone and 4-benzoyl-4'-methyldiphenyl sulfide; Thioxanthone photopolymerization initiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropyl thioxanthone and 2,4-diisopropyl thioxanthone; 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis- (Trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl ) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho-1-yl) -4,6-bis (trichloromethyl)- s-triazine, 2- (4-methoxy-naphtho-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) Triazine photopolymerization initiators such as -6-triazine and 2,4-trichloromethyl (4'-methoxystyryl) -6-triazine; Borate photopolymerization initiator, carbazole photopolymerization initiator, and imidazole photopolymerization initiator. The photopolymerization initiator may be used in the amount of 5 to 200 parts by weight, preferably 10 to 150 parts by weight, per 100 parts by weight of the pigment in the coloring composition.

The photopolymerization initiators may be used alone or in combination. As a sensitizer, α-acyloxyester, acylphosphine oxide, methylphenyl glyoxylate, benzyl-9,10-phenanthrene quinone, camphor quinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3 , 3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone and 4,4'-diethylaminobenzophenone can additionally be used. The sensitizer may be used in the amount of 0.1 to 60 parts by weight per 100 parts by weight of the photopolymerization initiator in the coloring composition.

The color composition for color filters of the present invention 3 may be prepared in the form of a solvent developing type or an alkali developing type colored resist. In coloring resists, the pigments are dispersed in pigment carriers and monomers, including thermoplastic resins, thermosetting resins or active energy beam curable resins. The colored resist finely disperses one or at least two kinds of fine organic pigment (s) or, optionally, with a photopolymerization initiator, a three-roll mill, two-roll mill, sand mill, kneader or attritor It can be prepared by finely dispersing the pigment carrier with a dispersing device such as an attritor. Furthermore, the coloring composition for color filters provided by the present invention can also be prepared by dispersing at least two kinds of the fine pigments individually in a pigment carrier to prepare a dispersion, and then mixing the dispersion.

When the pigment is dispersed in the pigment carrier, a dispersion aid such as a resin type pigment dispersant, a surfactant, the aforementioned pigment derivative, an anthraquinone derivative, an acridon derivative or a triazine derivative may be used as necessary. Dispersion aids are excellent in dispersing pigments and have an excellent effect of preventing re-agglomeration of pigments after dispersion, so that a color filter having excellent transparency is obtained when a coloring composition obtained by dispersing a pigment in a pigment carrier using the dispersion aid is used. Lose. Dispersion aids may be used in amounts of 0.1 to 40 parts by weight, preferably 0.1 to 30 parts by weight, per 100 parts by weight of pigment in the coloring composition.

Of these dispersion aids, pigment derivatives, anthraquinone derivatives, acridon derivatives and triazine derivatives (hereinafter, generally referred to as "derivatives") are preferred as dispersion aids. These derivatives are excellent in preventing aggregation of fine organic pigments and maintaining finely dispersed states of organic pigments, and high color purity can be obtained by using a coloring composition containing at least one of these derivatives. Because.

The resin type pigment dispersant has a pigment affinity site, which is a site having a property of absorbing pigment, and a site compatible with the pigment carrier, and serves to stabilize dispersion of the pigment in the pigment carrier by being absorbed by the pigment. Resin-type pigment dispersants are, in particular, polycarboxylic acid esters represented by polyurethanes, polyacrylates, unsaturated polyamides, polycarboxylic acids, (partial) amine salts of polycarboxylic acids, ammonium salts of polycarboxylic acids, Alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and modified products thereof, or polyesters with free carboxyl groups; Oily dispersants such as amides or salts thereof formed by the reaction of poly (lower alkyleneimines); Water-soluble resins or water-soluble polymer compounds such as (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (meth) acrylate ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol or polyvinyl pyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide and phosphate esters. These resin type pigment dispersants may be used alone or in combination.

Surfactants include polyoxyethylene alkyl ether sulfates, sodium dodecylbenzenesulfonates, alkali salts of styrene-acrylic acid copolymers, sodium alkylnaphthalenesulfonates, sodium alkyldiphenyl ether disulfonates, monoethanolamine lauryl sulfate, Anionics such as triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymers and polyoxyethylene alkyl ether phosphate esters Surfactants; Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate and polyethylene glycol monolaurate ; Cationic surfactants such as quateranry alkylammonium salts and their ethylene oxide adducts; And amphoteric surfactants such as alkyl betaine, represented by alkyldimethylaminoacetic acid betaine, and alkylimidazoline. These surfactants can be used alone or in combination.

The coloring composition for color filters provided by the present invention 3 sufficiently disperses the pigment in a pigment carrier, and applies a dry film having a thickness of 0.2 to 5 탆 to the coloring composition on a transparent substrate such as a glass substrate to form a filter segment. Solvents may be included for the purpose of promoting their formation.

Examples of the solvent include 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, 3-ethoxyethylpropionate, 3- Methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutylacetate, 3-methoxybutanol, 3-methoxy butyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpi Lollidon, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, Isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethyl Glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiarybutyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl Ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, di Ethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimeth Ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether , Tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene Glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl Acetates, isoamyl acetate, isobutyl acetate, propyl acetate and dibasic esters. These solvents may be used alone or in combination. The solvent may be used in an amount of 800 to 4,000 parts by weight, preferably 1,000 to 2,500 parts by weight per 100 parts by weight of the pigment in the coloring composition.

In addition, the coloring composition for color filters provided by the present invention 3 may include a storage stabilizer for the purpose of stabilizing the viscosity of the composition over time. Examples of such storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, t-butylpyrocatechol, triethylphosphine and triphenyl Organic phosphines such as phosphines and phosphoric acid salts. The storage stabilizer may be used in an amount of 0.1 to 10 parts by weight per 100 parts by weight of the pigment in the coloring composition.

The coloring composition for color filters provided by the present invention 3 may include a dye for toning, as long as the heat resistance thereof is not reduced.

Using a centrifugal separation, precipitation filter or membrane filter, 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more of coarse particles and mixed dust from the coloring composition of the invention 3 It is good to remove.

Next, the color filter of this invention 3 is demonstrated.

The color filter of the present invention 3 is composed of R (red), G (green), B (blue; blue), Y (yellow), M (magenta) and the like formed on the surface of a transparent or reflective substrate. At least two color filter segments selected from C (cyan). The filter segment of each color can be formed by using the coloring composition for color filters provided by this invention according to the printing method or the photolithography method. As the transparent substrate, glass plates and resin plates such as polycarbonate, methyl polymethacrylate, and polyethylene terephthalate can be used.

In the formation of each color filter segment by the printing method, the pattern formation can only be performed by repeating printing and drying the coloring composition for color filters prepared as the above various printing inks, so the printing method is a low cost method, and It is a color filter manufacturing method that is excellent for production. In addition, with the improvement of printing technology, fine patterns with high dimensional accuracy and flatness can be printed. For printing, such a configuration is preferable because the ink is not dried, but is solidified on a printing plate or a blanket. Control of the traceability of the ink on the printing machine is also important, and the viscosity of the ink can be adjusted with dispersant and extender pigments.

When each color filter segment is formed by the photolithography method, a coloring composition prepared as a solvent development type or an alkali development type color resist is coated on a transparent substrate by a coating method such as spray coating, spin coating, slit coating or roll coating. To a dry thickness of from 5 μm. If desired, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or without contact with the film. The film is then immersed in a solvent or alkaline developer, or sprayed with a developer, the uncured portion is removed to form the desired pattern, and the same procedure is repeated for the other colors. In this way, a color filter is produced. In order to enhance the polymerization of the coloring resist, heating may be performed as necessary. According to the photolithography method, a color filter can be manufactured and has a much higher precision than the case by the printing method.

In development, an aqueous sodium carbonate or aqueous sodium hydroxide solution is used as the alkali developer, and organic alkalis such as dimethylbenzylamine and triethanol amine can also be used. Foaming inhibitors or surfactants may be added to the developer.

In order to increase the sensitivity of ultraviolet exposure, ultraviolet exposure is a resin which is coated and dried with a colored resist and which is alkali-aqueous-solution-soluble in water-soluble or alkaline aqueous solution such as polyvinyl alcohol or water-soluble acrylic resin. Can be carried out after coating and drying to form a film to prevent polymerization inhibition due to oxygen.

The color filter of the present invention 3 can also be manufactured by an electrodeposition method or a transferring method other than the above-described method. The coloring composition of the present invention can be prepared by any method. Electrodeposition is a method in which each color filter segment is electrodeposited-formed on a transparent electrically conductive film formed on a transparent substrate by electrophoresis of colloidal particles to form a curley filter. The transfer method is a method in which a color filter layer is formed on a surface of a separable transfer base sheet in advance, and then the color filter layer is moved onto a desired transparent substrate.

Example

Hereinafter, the present invention will be described in detail with reference to Examples and Comparative Examples of Conventional Methods. However, the present invention is not limited to these examples. In an embodiment, "part" means "parts by weight" and "%" means "% by weight".

Example 1

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As organic pigment, 600 parts of sodium chloride as water-soluble inorganic salt, 100 parts of diethylene glycol as water-soluble organic liquid and rosin ester as resin Five parts (Ester gumAT provided by Arakawa Chemical Industries, Ltd.) were pre-mixed for approximately five minutes with a converter mixer (Asada Iron Works. Co., LTD.). The resulting mixture was fed to a continuous kneader 10 ("Miracle K.C.K.-Type 42" provided by Asada Iron Works. Co., LTD.) Via a screw type metering feeder (metering feeder section 4 in FIG. 1). The continuous kneader 10 had a feed section screw diameter of 120 mmφ and had eight sets of dough sections consisting of a fixed disk and a rotating disk. The continuous kneader 10 was operated at a dough composition extrusion amount of 21 kg / hour, a main shaft rotation speed of 50 rpm and a dough temperature of 90 ° C. The power consumption for the dough was 1.8 kwh per kg of pigment. The kneaded composition thus obtained was taken and poured into 5,000 parts of water having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, and then filtered, washed with water and dried to obtain a pigment composition.

10 parts of the pigment composition was mixed with 90 parts of varnish for gravure ink (12% cellulose nitrate resin, 33% ethyl acetate, 30% toluene, 15% isopropyl alcohol, and 10% methanol) and 100 parts of 3-mm glass beads. . The gravure ink was prepared by dispersing for 60 minutes using a paint conditioner. The gravure ink was coated on a transparent film using bar coater # 4. White paper and black paper were placed on the black surface of the coating thus obtained. Color measurements were each performed using a colorimeter. The difference (ΔL *) of luminance L * was 5.2. ΔL * is usually used as a reference for transparency. If ΔL * is large, transparency is excellent.

The comparative examples 1 and 2 which performed the dough using the double arm dough machine which has the capacity of 1000 volume of the commonly used are shown below. Comparative example 1 is an example which does not contain resin which is a general kneading material structure. Although the power consumption in Example 1 was smaller than the power consumption in Comparative Example 1, the gravure ink coating of Example 1 was superior in transparency to Comparative Example 1. Comparative Example 2 is an example in which the same components as in Example 1 containing the resin were used. The gravure ink coating of Comparative Example 1 was superior in transparency than Comparative Example 1. The addition effect of the resin was found. However, the transparency of Example 1 was superior to Comparative Example 2. In the kneading apparatus, the continuous kneader was superior to the double arm kneader.

The comparative examples 3 and 4 in which the kneading material containing no resin and the continuous kneader used in Example 1 were used are shown below. Although the dough conditions in Comparative Example 3 were the same as in Example 1, the transparency of the gravure coating in Comparative Example 3 was poor. Therefore, the resin addition effect was recognized in Example 1. Comparative Example 4 is an example in which dough energy was increased by reducing the amount of water-soluble organic liquid used in Comparative Example 3 and doubling the power consumption. In Comparative Example 4, the transparency of the gravure ink coating was about the same as in Comparative Example 3. When the dough material did not contain a resin, there was a limit in improving the transparency of the gravure ink coating.

From the above results, it can be seen that a pigment composition having excellent substantial quality represented by transparency can be obtained using a small amount of energy due to the use of a continuous kneader and the incorporation of the resin into the dough material.

Comparative Example 1

Capacity of 1000 parts by volume of Blue 15 (T-95 Crude Blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt and 100 parts of diethylene glycol as a water-soluble organic liquid Put in a double arm dough. The mixture was kneaded at 90 ° C. for 5 hours while maintaining a dense dough state. The power consumption required for the dough was 4.1 kwh per kg of pigment. The kneaded composition thus obtained was taken and poured into 5,000 parts of water having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, and then filtered, washed with water and dried to obtain a pigment composition. A coating was obtained using the pigment composition in the same manner as in Example 1. ΔL * of the coating was 1.2.

Comparative Example 2

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As organic pigment, 600 parts of sodium chloride as water-soluble inorganic salt, 100 parts of diethylene glycol as water-soluble organic liquid and rosin ester as resin Five parts (Ester gumAT provided by Arakawa Chemical Industries, Ltd.) were placed in a double arm dough machine having a capacity of 1000 parts by volume. The mixture was kneaded at 90 ° C. for 5 hours while maintaining a dense dough state. The power consumption required for the dough was 4.1 kwh per kg of pigment. The kneaded composition thus obtained was taken and poured into 5,000 parts of water having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, and then filtered, washed with water and dried to obtain a pigment composition. A coating was obtained using the pigment composition in the same manner as in Example 1. ΔL * of the coating was 2.3.

Comparative Example 3

100 parts of Blue 15 (T-95 Crude Blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt and 100 parts of diethylene glycol as a water-soluble organic liquid converter mixer (Asada Iron Works. Co., Ltd.) was pre-mixed for almost 5 minutes. The mixture was kneaded and treated with a continuous kneader 10 in the same manner as in Example 1 to obtain a pigment composition. The power consumption required for the dough was 1.8 kwh per kg of pigment. The ΔL * of the coating obtained therefrom was 1.2.

[Comparative Example 4]

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt and 80 parts of diethylene glycol as a water-soluble organic liquid converter mixer (Asada Iron Works. Co., Ltd.) was pre-mixed for almost 5 minutes. The mixture was kneaded and treated with a continuous kneader 10 in the same manner as in Example 1 to obtain a pigment composition. The extrusion amount of the dough composition was 18 kg / hour. The power consumption required for the dough was 3.6 kwh per kg of pigment. The ΔL * of the coating obtained therefrom was 3.7.

Example 2-4

Except that the resin was replaced with synthetic rosin (Dymerex resin provided by Rika Hercules), unbalanced rosin (Rondis R provided by Arakawa Chemical Industries, Ltd.), and hydrogenated rosin (Staybelite resin provided by Rika Hercules) And a pigment composition was obtained in the same manner as in Example 1. Table 1 shows the power consumption required for the dough and the ΔL * value of the coating.

ΔL * of each coating was higher than Comparative Examples 1-4, and each coating was excellent in transparency.

Example 5-7 and Comparative Example 5-7

The dough materials having the constitution shown in Table 1 were kneaded under the kneading conditions shown in Table 1, respectively. Each of these materials was treated in the same manner as in Example 1 to obtain a pigment composition. The organic pigments used in Example 5 and Comparative Example 5 were CIPigment Yellow 138 (Paliotol Yellow K0691HD provided by BASF), and the organic pigments used in Examples 6 and 6 were CIPigment Red 177 (Ciba Specialty Chemicals). Chromophthal Red A2B) provided by Co., and the organic pigments used in Examples 7 and 7 were CIPigment Violet 23 (Sumiton Fast Violt RL Base provided by Sumitomo Chemical Co., Ltd.).

The ΔL * values of the coatings prepared from the pigment compositions obtained at low power consumption in Examples 5-7 were greater than Comparative Examples 5-7 and the transparency of Examples 5-7 was excellent.

Table 1

Kneader people Dough temperature ℃ Extrusion amount or dough time Power consumption kwh / kg Ex.1 Continuous kneader 90 21 kg / hour 1.8 CEx.1 Double arm kneader 90 5 hours 4.1 CEx.2 Double arm kneader 90 5 hours 4.1 CEx.3 Continuous kneader 90 21 kg / hour 1.8 CEx.4 Continuous kneader 90 18 kg / hour 3.6 Ex.2 Continuous kneader 90 21 kg / hour 1.8 Ex.3 Continuous kneader 90 21 kg / hour 1.8 Ex.4 Continuous kneader 90 21 kg / hour 1.8 Ex.5 Continuous kneader 80 21 kg / hour 1.6 CEx.5 Double arm kneader 80 5 hours 3.4 Ex.6 Continuous kneader 100 21 kg / hour 2.2 CEx.6 Double arm kneader 100 5 hours 4.2 Ex.7 Continuous kneader 80 21 kg / hour 2.3 CEx.7 Double arm kneader 80 5 hours 4.7

Ex. = Example, CEx. = Comparative Example

Table 1 (continued)

Composition of dough ingredients Transparency of gravure ink coating ΔL * Organic pigment Water-soluble inorganic salts Water soluble organic liquid Suzy persons amount amount amount persons amount Ex.1 Blue 15 100 600 100 Rosin ester 5 5.2 CEx.1 Blue 15 100 600 100 radish - 1.2 CEx.2 Blue 15 100 600 100 Rosin ester 5 2.3 CEx.3 Blue 15 100 600 100 radish - 3.6 CEx.4 Blue 15 100 600 80 radish - 3.7 Ex.2 Blue 15 100 600 100 Synthetic rosin 5 4.8 Ex.3 Blue 15 100 600 100 Unbalanced Rosin 7 5.3 Ex.4 Blue 15 100 600 100 Hydrogenated Rosin 3 4.6 Ex.5 Yellow 138 100 500 90 Rosin ester 5 6.5 CEx.5 Yellow 138 100 500 90 radish - 1.8 Ex.6 Red 177 100 1,000 140 Rosin ester 5 5.4 CEx.6 Red 177 100 1,000 140 radish - 1.4 Ex.7 Violet 23 100 1,000 150 Rosin ester 5 5.6 CEx.7 Violet 23 100 1,000 150 radish - 1.5

Ex. = Example, CEx. = Comparative Example

Example 8

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt, 100 parts of diethylene glycol as a water-soluble organic liquid and the compound as a derivative (1) Five parts were pre-mixed for approximately 5 minutes with a converter mixer (Asada Iron Works. Co., Ltd.). The resulting mixture was fed to a continuous kneader 10 ("Miracle K.C.K.-Type 42" provided by Asada Iron Works. Co., LTD.) Via a screw type metering feeder (metering feeder section 4 in FIG. 1). The continuous kneader 10 had a feed section screw diameter of 120 mmφ and had eight sets of dough sections consisting of a fixed disk and a rotating disk. The continuous kneader 10 was operated at a dough composition extrusion amount of 21 kg / hour, a main shaft rotation speed of 50 rpm and a dough temperature of 100 ° C. The power consumption for the dough was 1.7 kwh per kg of pigment. The kneaded composition thus obtained was taken and poured into 5,000 parts of water having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, and then filtered, washed with water and dried to obtain a pigment composition. The pigment composition had a specific surface area of 90 m 2 / g by the BET method. 10 parts of the pigment composition was mixed with 90 parts of varnish for gravure ink (12% cellulose nitrate resin, 33% ethyl acetate, 30% toluene, 15% isopropyl alcohol, and 10% methanol) and 100 parts of 3-mm glass beads. . The gravure ink was prepared by dispersing for 60 minutes using a paint conditioner. The gravure ink was coated on a transparent film using bar coater # 4. The coating thus obtained was measured for 60 ° -glossiness. Glossiness was 82%.

The comparative examples 8 and 9 which performed the dough using the double arm dough machine which has the capacity of 1000 volume of the commonly used are shown below. Comparative Example 8 is an example containing no derivative which is a general kneading material constitution. Although the power consumption in Example 8 was smaller than that of Comparative Example 8, the specific surface area of the pigment composition of Example 8 was larger than that of Comparative Example 8, and the pigment composition of Example 8 was finely separated. divided). The glossiness of the gravure ink coating of Example 8 was high and therefore of substantial quality. Comparative Example 9 is an example in which the same components as in Example 8 including the derivative are used. The specific surface area of the pigment composition of Comparative Example 9 was high and the glossiness of the gravure ink coating thereof was high as compared with Comparative Example 8. Thus, the effect of addition of the derivative was found. However, the effect in Example 8 was superior to the effect in Comparative Example 9. In the kneading apparatus, the continuous kneader was superior to the double arm kneader.

Comparative Examples 10 and 11 in which the dough material does not contain a derivative and in which the continuous dough machine used in Example 8 is used are shown below. Although the kneading conditions in Comparative Example 10 were the same as in Example 8, the specific surface area of the pigment composition of Comparative Example 10 was small and the gloss of the gravure ink coating thereof was poor. In Example 8, the effect of addition of the derivative was recognized. Comparative Example 11 is an example in which the dough energy was increased by reducing the amount of water-soluble organic liquid used in Comparative Example 10 and doubling the power consumption. The specific surface area of the pigment composition and the glossiness of the gravure ink coating in Comparative Example 11 were approximately the same as in Comparative Example 10. If the dough material did not contain such derivatives, there was a limit to the fine-separating process and the substantial quality.

From the above results, it has been found that due to the use of the continuous kneader and the incorporation of the derivatives of the invention in the kneading material, micro-separation of the pigment can be achieved using a small amount of energy and the substantial quality is improved.

Comparative Example 8

Capacity of 1000 parts by volume of Blue 15 (T-95 Crude Blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt and 100 parts of diethylene glycol as a water-soluble organic liquid Put in a double arm dough. The mixture was kneaded at 100 ° C. for 5 hours while maintaining a dense dough state. The power consumption required for the dough was 4.0 kwh per kg of pigment. The resulting kneaded composition was taken and poured into 5,000 parts of water having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, and then filtered, washed with water and dried to obtain a pigment composition. The pigment composition had a specific surface area of 69 m 2 / g by the BET method. The coating was obtained in the same manner as in Example 8. The glossiness of the coating was 66%.

Comparative Example 9

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt, 100 parts of diethylene glycol as a water-soluble organic liquid and the compound as a derivative (1) Five parts were put into a double arm kneader having a capacity of 1000 parts by volume. The mixture was kneaded at 100 ° C. for 5 hours while maintaining a dense dough state. The power consumption required for the dough was 4.1 kwh per kg of pigment. The kneaded composition thus obtained was taken and poured into 5,000 parts of water having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, and then filtered, washed with water and dried to obtain a pigment composition. The pigment composition had a specific surface area of 77 m 2 / g by the BET method. The coating was obtained in the same manner as in Example 8. The glossiness of the coating was 72%.

Comparative Example 10

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt and 100 parts of diethylene glycol as a water-soluble organic liquid converter mixer (Asada Iron Works. Co., Ltd.) was pre-mixed for almost 5 minutes with almost uniformity. The mixture was kneaded and treated with a continuous kneader 10 in the same manner as in Example 8 to obtain a pigment composition. The power consumption required for the dough was 1.7 kwh per kg of pigment. The pigment composition had a specific surface area of 81 m 2 / g by the BET method. The glossiness of its coating was 75%.

Comparative Example 11

100 parts of Blue 15 (T-95 crude blue provided by ZHUHAI TOYO INK CO., LTD.) As an organic pigment, 600 parts of sodium chloride as a water-soluble inorganic salt and 80 parts of diethylene glycol as a water-soluble organic liquid converter mixer (Asada Iron Works. Co., Ltd.) was pre-mixed for almost 5 minutes. The mixture was kneaded and treated with a continuous kneader 10 in the same manner as in Example 8 to obtain a pigment composition. The dough composition extrusion capacity was 18 kg / hour. The power consumption required for the dough was 3.5 kwh per kg of pigment. The pigment composition had a specific surface area of 82 m 2 / g according to the BET method. The glossiness of its coating was 76%.

Example 9-11

The pigment composition was obtained in the same manner as in Example 8 except that the derivative used in Example 8 was replaced with Compound (2), Compound (3) and Compound (4), respectively. Table 2 shows the power consumption required for the dough, the specific surface area according to the BET method and the glossiness of the coating.

The BET-method specific surface area and glossiness of the coating of the pigment composition in Examples 9-11 were higher than in Comparative Examples 8-11.

Example 12-14 and Comparative Example 12-14

The kneading material having the configuration shown in Table 2 was kneaded under the kneading conditions shown in Table 2, respectively. Each of these materials was treated in the same manner as in Example 8 to obtain a pigment composition. The organic pigments used in Example 12 and Comparative Example 12 were CIPigment Red 122 (Hostaperm Pink E provided by Clariant), and the organic pigments used in Example 13 and Comparative Example 13 were CIPigment Red 177 (Ciba Specialty Chemicals Co.). Chromophthal Red A2B), and the organic pigments used in Example 14 and Comparative Example 14 were CIPigment Violet 23 (Sumiton Fast Violt RL Base provided by Sumitomo Chemical Co., Ltd.).

The BET-method specific surface area and the glossiness of the coating of the pigment composition prepared in a small amount of power consumption in Examples 12-14 were higher than that of Comparative Example 12-14.

TABLE 2

Kneader people Dough temperature ℃ Extrusion amount or dough time Power consumption kwh / kg Ex.8 Continuous kneader 100 21 kg / hour 1.7 CEx.8 Double arm kneader 100 5 hours 4.0 CEx.9 Double arm kneader 100 5 hours 4.1 CEx.10 Continuous kneader 100 21 kg / hour 1.7 CEx.11 Continuous kneader 100 18 kg / hour 3.5 Ex.9 Continuous kneader 100 21 kg / hour 1.7 Ex.10 Continuous kneader 100 21 kg / hour 1.7 Ex.11 Continuous kneader 100 21 kg / hour 1.7 Ex.12 Continuous kneader 120 21 kg / hour 1.6 CEx.12 Double arm kneader 120 5 hours 3.4 Ex.13 Continuous kneader 100 21 kg / hour 2.2 CEx.13 Double arm kneader 100 5 hours 4.2 Ex.14 Continuous kneader 80 21 kg / hour 2.3 CEx.14 Double arm kneader 80 5 hours 4.7

Ex. = Example, CEx. = Comparative Example

Table 2 (continued)

Composition of dough ingredients Specific surface area ㎡ / g Gravure Ink Coating Gloss% Organic pigment Water-soluble inorganic salts Water soluble organic liquid derivative persons amount amount amount Compound number amount Ex.8 Blue 15 100 600 100 (One) 5 90 82 CEx.8 Blue 15 100 600 100 radish - 69 66 CEx.9 Blue 15 100 600 100 (One) 5 77 72 CEx.10 Blue 15 100 600 100 radish - 81 75 CEx.11 Blue 15 100 600 80 radish - 82 76 Ex.9 Blue 15 100 600 100 (2) 5 92 83 Ex.10 Blue 15 100 600 100 (3) 10 88 80 Ex.11 Blue 15 100 600 100 (4) 5 91 82 Ex.12 Red 122 100 500 80 (5) 5 72 77 CEx.12 Red 122 100 500 80 radish - 60 62 Ex.13 Red 177 100 1,000 140 (6) 5 93 85 CEx.13 Red 177 100 1,000 140 radish - 65 54 Ex.14 Violet 23 100 1,000 150 (7) 5 90 81 CEx.14 Violet 23 100 1,000 150 radish - 70 63

Ex. = Example, CEx. = Comparative Example

Prior to the examples which follow, the method of measuring the average primary particle diameter, aspect ratio and specific surface area of the pigment, and the contrast ratio of the resist coating film, and the preparation examples of the acrylic resin used in the examples are described.

The primary particle diameter of the pigment is measured by the general method in which the size of the primary particles is specified directly from the electron microscope. Specifically, the major axis diameter and minor axis diameter of the pigment primary particles are measured, and the average of the major axis diameter and minor axis diameter is adopted as the particle diameter of the pigment particles. For 100 or more pigment particles, the volume (weight) of each particle was obtained respectively by generating an approximation to the hexahedron of its particle diameter as obtained above, and the volume average particle diameter was adopted as the average primary particle diameter. When measuring with both transmission electron microscope (TEM) and scanning electron microscope (SEM), almost identical results are obtained.

The aspect ratio of the pigment was obtained by measuring the major and minor axis diameters of the primary particles of the pigment with an electron microscope, respectively, and calculating based on the following equation. The closer the aspect ratio is to 1, the closer the crystal form of the particles is to the square.

(Aspect ratio) = (long axis diameter) / (short axis diameter)

The specific surface area of the pigment particles was obtained by the BET method based on nitrogen adsorption. The measurement was performed using an automatic vapor adsorption amount measuring device ("BELSORP 18" provided by BEL Japan, Inc.).

Next, the contrast ratio measurement method of the coating film produced using the resist is described with reference to FIG. The light emitted from the backlight unit 7 for liquid crystal display passes through the polarizing plate to be polarized, and the polarized light passes through the dry coating film 4 of the coloring composition coated on the glass substrate and the polarizing plate 3 ) When the polarization plan of the polarization plate 6 and the polarization plan of the polarization plate 3 are parallel, the polarization plate 3 transmits light. When the polarization plan is orthogonal, the polarization plate 3 blocks light.

However, when light polarized by the polarizing plate 6 passes through the dry coating film 4 of the coloring composition, scattering occurs due to the pigment particles, and deflection occurs in part of the polarization plan. In this case, when the polarizing plates are parallel, the amount of light passing through the polarizing plate 3 decreases. When the polarizing plates are orthogonal, the polarizing plates 3 transmit part of the light. This transmitted light is measured by the luminance on the polarizing plate. The ratio (contrast ratio) of the luminance when the polarizing plates are parallel and the luminance when the polarizing plates are orthogonal was calculated.

(Contrast ratio) = (parallel brightness) / (orthogonal brightness)

Therefore, when scattering occurs due to the pigment in the dry coating film 4 of the coloring composition, the parallel brightness decreases and the orthogonal brightness increases. Therefore, the contrast ratio is reduced.

As the luminance meter 1, a color luminance meter (" BM-5A " provided by Topcon) was used and a polarization plate (" NPF-G1220DUN " provided by Nitto Denko Corporation) was used as the polarization plate. In the measurement, a black mask 2 having a 1 × 1 cm square hole was placed in the measurement section to block unnecessary light.

(Production Example of Acrylic Resin Solution Used in Examples)

800 parts of cyclohexanone were placed in a reaction vessel and heated to 100 ° C. while introducing nitrogen gas into the reaction vessel. A polymerization was carried out by dropwise adding a mixture of 60.0 parts of styrene, 60.0 parts of methacrylic acid, 65.0 parts of methyl methacrylate, 65.0 parts of butyl methacrylate, and 10.0 parts of azobisisobutyronitrile dropwise to the reaction vessel at the same temperature over 1 hour. It was. After dropping, the resulting mixture was allowed to react further at 100 ° C. for 3 hours. Then, a solution of 2.0 parts of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added. The mixture was allowed to react for an additional hour to obtain an acrylic resin solution having a weight average molecular weight of about 40,000 as measured by GPC.

The acrylic resin solution was cooled to room temperature and then a portion of the resin solution was sampled. The sampled resin solution was dried at 180 ° C. for 20 minutes and the non-volatile content was measured. An acrylic resin solution was prepared by adding cyclohexanone to the resin solution such that the non-volatile content was 20%.

Example 15

100 parts of "T-95 Crude Blue" provided by ZHUHAI TOYO INK CO., LTD., 100 parts of sodium chloride and 10 parts of diethylene glycol (Asada Iron Works. Co., LTD.) Pre-mix for 5 min. The resulting mixture was fed to a continuous kneader 10 ("Miracle KCK-Type 42" provided by Asada Iron Works. Co., LTD.) Via a screw type metering feeder (metering feeder section 4 of FIG. 1) and the mixture was fed. Kneading The continuous kneader had a feed section screw diameter of 120 mmφ and had eight sets of dough sections consisting of a fixed disk and a rotating disk. The continuous kneader was operated at a dough composition extrusion amount of 21 kg / hour, a main shaft rotation speed of 50 rpm and a grinding temperature of 100 ° C. The kneaded composition thus obtained was taken and poured into 1,300 parts of a 1% sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and pulverized to obtain a fine copper phthalocyanine pigment. The fine copper phthalocyanine pigment had a specific surface area of 111 m 2 / g. Observed by TEM (electron microscopy), the average primary particle diameter was 23.1 nm, the pigment particles were completely finely separated and no coarse particles were found. The aspect ratio was 1.61.

Then, the mixture having the following constitution comprising the obtained fine copper phthalocyanine pigment was uniformly stirred, and then Eiger mill (“Minimodel M-250 MKII” provided by Eiger Japan) using zirconia beads having a diameter of 1 mm. The dispersion was carried out for 5 minutes, and filtered with a 5-µm filter to prepare a blue pigment dispersion.

10.0 parts of fine copper phthalocyanine pigment

Derivative 48 (pigment derivative) 1.0 part

1.0 parts of phosphate ester pigment dispersant ("BYK111" provided by BYK Chemie)

40.0 parts acrylic resin solution

Cyclohexanone 48.0 parts

In addition, an alkali developing type blue resist was prepared by uniformly mixing the mixture having the following composition including the obtained blue dispersion and then filtering with a 1 μm filter.

Blue dispersion 45.0 parts

15.0 parts acrylic resin solution

9.0 parts of trimethylol propane triacrylate

Shin-Nakamura Chemical Co., ltd.

2.0 parts of photoinitiators

("Irgacure 907" provided by Ciba Specialty Chemicals Co.)

0.2 parts of a photosensitizer

("EAB-F" provided by Hodogaya Chemical Co., Ltd.)

Cyclohexanone 28.8 parts

Comparative Example 15

100 parts of "T-95 Crude Blue" provided by ZHUHAI TOYO INK CO., LTD., 100 parts of sodium chloride and 10 parts of diethylene glycol were placed in a double arm kneader having a capacity of 1000 parts skin. The mixture was kneaded at 100-110 ° C. for 5 hours while maintaining a dense dough. After grinding, the resulting mixture was taken and poured into 1,300 parts of a 1% aqueous sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and pulverized to obtain a fine copper phthalocyanine pigment. The fine copper phthalocyanine pigment had a specific surface area of 93 m 2 / g. Observed by TEM (electron microscopy), the pigment particles were completely finely separated and no coarse particles were found. However, the average primary particle diameter was 272.3 nm and the aspect ratio was 1.75.

An alkali developing type blue resist was prepared in the same manner as in Example 15 using the obtained fine copper phthalocyanine pigment.

Example 16

A dough composition containing 100 parts of quinophthalone pigment (CI Pigment Yellow 138, "Paliotol Yellow K0961HD" provided by BASF), 3,000 parts of sodium chloride and 700 parts of diethylene glycol was fed to the same continuous kneader as used in Example 15 and The composition was kneaded at a dough composition extrusion amount of 25 kg / hour, a main shaft rotation speed of 50 rpm and a grinding temperature of 110 ° C. The dough thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine quinophthalone pigment. The fine quinophthalone pigment had a specific surface area of 115 m 2 / g. When observed by TEM (electron microscopy), the average primary particle diameter was 33.2 nm, the pigment particles were completely separated finely and no coarse particles were found. The aspect ratio was 1.53.

Then, the mixture having the following constitution comprising the obtained fine quinophthalone pigment was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a yellow pigment dispersion. An alkali developing type yellow resist was also prepared in the same manner as in Example 15 using the obtained yellow pigment dispersion.

Part 10.0 Fine Quinolphthalone Pigment

Derivative 39 (pigment derivative) 1.0 part

1.0 parts of phosphate ester pigment dispersant ("BYK111" provided by BYK Chemie)

40.0 parts acrylic resin solution

Cyclohexanone 48.0 parts

[Comparative Example 16]

100 parts of quinophthalone pigment (C.I. Pigment Yellow 138, "Paliotol Yellow K0961HD" provided by BASF), 3,000 parts of sodium chloride and 700 parts of diethylene glycol were placed in a double arm dough machine having a capacity of 1000 parts by volume. The mixture was kneaded at 100-110 ° C. for 6 hours while maintaining a dense dough. After grinding, the resulting mixture was taken and poured into 1,300 parts of a 1% aqueous sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and pulverized to thereby obtain a fine quinophthalone pigment. The fine quinophthalone pigment had a specific surface area of 95 m 2 / g. Observed by TEM (electron microscopy), the pigment particles were completely finely separated and no coarse particles were found. However, the average primary particle diameter was 82.5 nm and the aspect ratio was 1.72.

An alkali developing type yellow resist was produced in the same manner as in Example 16 using the obtained fine quinophthalone pigment.

Example 17

A dough composition containing 100 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254, "IRGAPHOR RED B-CF" provided by Ciba Specialty Chemicals Co.), 2,000 parts of sodium chloride and 230 parts of diethylene glycol was used in Example 15 The same continuous kneader was fed and the composition was kneaded at a dough composition extrusion amount of 23 kg / hour, a main shaft rotation speed of 50 rpm and a grinding temperature of 60 ° C. The dough thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine diketopyrrolopyrrole pigment. The fine diketopyrrolopyrrole pigment had a specific surface area of 122 m 2 / g. Observed by TEM (electron microscopy), the average primary particle diameter was 35.2 nm, the pigment particles were completely finely separated and no coarse particles were found. The aspect ratio was 1.61.

Then, the mixture having the following constitution comprising the obtained fine diketopyrrolopyrrole pigment was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a red pigment dispersion. In addition, an alkali developing type red resist was prepared in the same manner as in Example 15 using the obtained red pigment dispersion.

10.0 parts fine diketopyrrolopyrrole pigment

Derivative 49 (pigment derivative) 1.0 part

1.0 parts of phosphate ester pigment dispersant ("BYK111" provided by BYK Chemie)

40.0 parts acrylic resin solution

Cyclohexanone 48.0 parts

[Comparative Example 17]

Double arm dough machine with a capacity of 1000 parts by volume of diketopyrrolopyrrole pigment (CI Pigment Red 254, "IRGAPHOR RED B-CF" provided by Ciba Specialty Chemicals Co.), 2,000 parts of sodium chloride and 230 parts of diethylene glycol Put in. The mixture was kneaded at 65-75 ° C. for 6 hours while maintaining a dense dough. After grinding, the resulting mixture was taken and poured into 20,000 parts of a 1% aqueous sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and ground to thereby obtain a fine diketopyrrolopyrrole pigment. The fine diketopyrrolopyrrole pigment had a specific surface area of 105 m 2 / g. Observed by TEM (electron microscopy), the pigment particles were completely finely separated and no coarse particles were found. However, the average primary particle diameter was 69.5 nm and the aspect ratio was 1.81.

An alkali developing type red resist was prepared in the same manner as in Example 17 using the obtained fine diketopyrrolopyrrole pigment.

Example 18

A dough composition containing 100 parts of crude dioxazine violet pigment (Sumiton Fast Violet RL Base provided by Sumitomo Chemical Co., Ltd.), 1,000 parts of sodium chloride and 150 parts of diethylene glycol was subjected to the same continuous as that used in Example 15. It was fed to the kneader and the composition was kneaded at a dough composition extrusion amount of 22 kg / hour, a main shaft rotation speed of 50 rpm and a grinding temperature of 100 ° C. The dough thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine dioxazine violet pigment. The fine dioxazine violet pigment had a specific surface area of 140 m 2 / g.

Observed by TEM (electron microscopy), the average primary particle diameter was 30.3 nm, the pigment particles were completely finely separated and no coarse particles were found. The aspect ratio was 1.63.

Then, the mixture having the following constitution comprising the obtained fine dioxazine violet pigment was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a purple pigment dispersion. An alkali developing type violet resist was also prepared in the same manner as in Example 15 using the obtained purple pigment dispersion.

Fine Dioxazine Violet Pigment Part 10.0

Derivative 48 (pigment derivative) 1.0 part

1.0 parts of phosphate ester pigment dispersant ("BYK111" provided by BYK Chemie)

40.0 parts acrylic resin solution

Cyclohexanone 48.0 parts

[Comparative Example 18]

100 parts of crude dioxazine violet pigment (Sumiton Fast Violet RL Base provided by Sumitomo Chemical Co., Ltd.), 1,000 parts of sodium chloride and 150 parts of diethylene glycol were placed in a double arm dough machine having a capacity of 1000 parts by volume. The mixture was kneaded at 100-110 ° C. for 5 hours while maintaining a dense dough. After grinding, the resulting mixture was taken and poured into 10,000 parts of a 1% aqueous sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and pulverized to obtain a fine dioxazine violet pigment. The fine dioxazine violet pigment had a specific surface area of 93 m 2 / g. Observed by TEM (electron microscopy), the pigment particles were completely finely separated and no coarse particles were found. However, the average primary particle diameter was 59.5 nm and the aspect ratio was 1.85.

An alkali developing type violet resist was prepared in the same manner as in Example 18 using the obtained fine dioxazine violet pigment.

Example 19

A dough composition was carried out containing 100 parts of "T-95 Crude Blue" provided by ZHUHAI TOYO INK CO., LTD., 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of rosin ester as resin. The same continuous kneader as used in Example 15 was fed and the composition was kneaded at a dough composition extrusion amount of 22 kg / hour, a main shaft rotation speed of 50 rpm, and a grinding temperature of 90 ° C. The dough thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine copper phthalocyanine pigment. The fine copper phthalocyanine pigment had a specific surface area of 128 m 2 / g. Observed by TEM (electron microscopy), the average primary particle diameter was 21.1 nm, the pigment particles were completely finely separated and no coarse particles were found. Aspect ratio was 1.54.

Then, the mixture having the following constitution comprising the obtained fine copper phthalocyanine pigment was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a blue pigment dispersion. An alkali developing type blue resist was also prepared in the same manner as in Example 15 using the blue pigment dispersion obtained above.

10.0 parts of fine copper phthalocyanine pigment

Derivative 48 (pigment derivative) 1.0 part

1.0 parts of phosphate ester pigment dispersant ("BYK111" provided by BYK Chemie)

40.0 parts acrylic resin solution

Cyclohexanone 48.0 parts

Comparative Example 19

Capacity of 100 parts by volume of 100 parts of "T-95 Crude Blue" provided by ZHUHAI TOYO INK CO., LTD., 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of rosin ester as resin It was put into a double arm dough machine. The mixture was kneaded at 90 ° C. for 5 hours while maintaining a dense dough state. After grinding, the resulting mixture was taken and poured into 1,300 parts of a 1% aqueous sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and pulverized to obtain a fine copper phthalocyanine pigment. The fine copper phthalocyanine pigment had a specific surface area of 97 m 2 / g. Observed by TEM (electron microscopy), the pigment particles were completely finely separated and no coarse particles were found. However, the average primary particle diameter was 68.9 nm and the aspect ratio was 1.71.

An alkali developing type blue resist was prepared in the same manner as in Example 15 using the obtained fine copper phthalocyanine pigment.

Example 20

Dough composition containing 100 parts of "T-95 Crude Blue" provided by ZHUHAI TOYO INK CO., LTD., 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of derivative 51 (pigment derivative) Was fed to the same continuous kneader as used in Example 15 and the composition was kneaded at a dough composition extrusion amount of 22 kg / hour, main shaft rotation speed of 50 rpm and grinding temperature of 100 ° C. The dough thus obtained was purified, filtered, dried and pulverized in the same manner as in Example 15 to obtain a fine copper phthalocyanine pigment. The fine copper phthalocyanine pigment had a specific surface area of 132 m 2 / g. Observed by TEM (electron microscopy), the average primary particle diameter was 20.2 nm, the pigment particles were completely finely separated and no coarse particles were found. The aspect ratio was 1.50.

Then, the mixture having the following constitution comprising the obtained fine copper phthalocyanine pigment was uniformly stirred, and then dispersed and filtered in the same manner as in Example 15 to obtain a blue pigment dispersion. An alkali developing type blue resist was also prepared in the same manner as in Example 15 using the blue pigment dispersion obtained above.

10.0 parts of fine copper phthalocyanine pigment

Derivative 48 (pigment derivative) 1.0 part

1.0 parts of phosphate ester pigment dispersant ("BYK111" provided by BYK Chemie)

40.0 parts acrylic resin solution

Cyclohexanone 48.0 parts

[Comparative Example 20]

1000 parts by weight of 100 parts of "T-95 Crude Blue" provided by ZHUHAI TOYO INK CO., LTD., 600 parts of sodium chloride, 100 parts of diethylene glycol and 5 parts of derivative 51 (pigment derivative) It was placed in a double arm dough machine having a capacity. The mixture was kneaded at 100 ° C. for 5 hours while maintaining a dense dough state. After grinding, the resulting mixture was taken and poured into 1,300 parts of a 1% aqueous sulfuric acid solution having a temperature of 70 ° C. The mixture was stirred for 1 hour while maintaining the temperature, then filtered, washed with water, dried and pulverized to obtain a fine copper phthalocyanine pigment. The fine copper phthalocyanine pigment had a specific surface area of 99 m 2 / g. Observed by TEM (electron microscopy), the pigment particles were completely finely separated and no coarse particles were found. However, the average primary particle diameter was 66.3 nm and the aspect ratio was 1.69.

An alkali developing type blue resist was prepared in the same manner as in Example 15 using the obtained fine copper phthalocyanine pigment.

Table 3 shows the measurement results of the specific surface area, average primary particle diameter, and aspect ratio of the fine pigments obtained in Examples 15-20 and Comparative Examples 15-20.

Three coated substrates having different film thicknesses associated with each resist obtained in Examples 15-20 and Comparative Examples 15-20 were prepared. Each film thickness and each contrast ratio was measured. From the data of the three coated substrates, a contrast ratio was obtained by first order correlation at a film thickness of 2 μm. Each coated substrate was prepared by varying the number of revolutions to have a film thickness of about 1 μm, applying a resist to the substrate with a spin coater, and then drying at 80 ° C. for 30 minutes in a hot-air oven.

The contrast ratio of the coated substrate prepared using the resist obtained in Examples 15-20 was higher than that of the coated substrate prepared using the resist obtained in Comparative Examples 15-20.

TABLE 3

Ex.15 Ex.16 Ex.17 Ex.18 Ex.19 Ex.20 Pigment Blue pigment 1 Yellow Pigment 1 Red pigment 1 Purple pigment 1 Blue pigment 2 Blue pigment 3 Specific surface area (㎡ / g) 111 115 122 140 128 132 Average primary particle diameter (nm) 23.1 33.2 35.2 30.3 21.1 20.2 Aspect ratio 1.61 1.53 1.61 1.63 1.54 1.50 Contrast Ratio 6,500 7,200 7,500 6,100 6,800 6,900

Ex. Example

Table 3 (continued)

CEx.15 CEx.16 CEx.17 CEx.18 CEx.19 CEx.20 Pigment Blue pigment 4 Yellow pigment 2 Red pigment 2 Purple pigment 2 Blue pigment 5 Blue Pigment 6 Specific surface area (㎡ / g) 93 95 105 93 97 99 Average primary particle diameter (nm) 72.3 82.5 69.5 59.5 68.9 66.3 Aspect ratio 1.75 1.72 1.81 1.85 1.71 1.69 Contrast Ratio 5,300 6,200 5,900 4,800 5,500 5,600

CEx. = Comparative Example

According to the method for producing the pigment composition provided by the present invention, it is possible to produce an appropriate amount in a timely manner because of the limitation of the production scale as compared with the conventional batch type half-kill. In addition, the method of the present invention also has the following advantages. Low quality deviation by lot. Since the kneader used is a closed kneader, the problem of contamination of the working environment and mixing of foreign substances due to the generation of powder dust is solved. The particles can be finely divided into fine particles with a small amount of energy. When the organic pigment obtained by the method of the present invention is dispersed in a colorant of an ink or coating such as gravure ink or offset ink, the pigment provides a good gloss and enhanced dyeing strength to the coated material. It is also particularly suitable for applications where transparency is required.

According to the colored composition for color filters provided by the present invention, since the colored composition includes organic pigments having fine particles having a uniform particle diameter which are difficult to obtain conventionally, the colored composition of the present invention is now used. A color filter having a higher contrast ratio can be formed.

Claims (10)

A mixture comprising organic pigments, water soluble inorganic salts, water soluble organic liquids and resins, a drive shaft, an annular fixed disk, a rotary disk concentric with the fixed disk and integrally rotating about an axis of the drive shaft, And kneading with a continuous kneader comprising an undifferentiated space formed in the gap between the fixed disk and the rotary disk. The method of claim 1 wherein the resin is a rosin resin. Organic dye derivatives, anthraquinone derivatives or triazine derivatives each containing at least one substituent selected from the group consisting of a phthalimidomethyl group, an amino group, a sulfonic acid group and a carboxylic acid group, an organic pigment, a water-soluble inorganic salt, and A mixture comprising a water soluble organic liquid is formed with a drive shaft, an annular fixed disc, a rotary disk concentric with the fixed disk and integrally rotating about an axis of the drive shaft; Method for producing a pigment composition comprising kneading with a continuous kneader comprising a pulverizing space formed in the interval between the rotary disks. The method of claim 1, wherein the organic pigment is an azo pigment, phthalocyanine pigment, quinacridone pigment, isoindolinone pigment, isoindolin pigment, perylene pigment, perinone pigment, diketopyrrolopyrrole pigment, thioindigo pigment, A dioxazine pigment, a quinophthalone pigment, an anthraquinone pigment or an indanthrone pigment. A colored composition for color filters comprising a transparent resin, precursors thereof or mixtures thereof, and a pigment carrier consisting of pigments, The pigment comprises a mixture comprising an organic pigment, a water soluble inorganic salt and a water soluble organic liquid concentric with the drive shaft, the annular fixed disc, the fixed disc and integrally around the axis of the drive shaft. A colored composition for a color filter comprising a fine organic pigment obtained by kneading with a continuous kneader comprising a rotating rotary disk and a micronized space formed in the gap between the fixed disk and the rotary disk. The colored composition according to claim 5, wherein 1 to 30 parts by weight of the water-soluble inorganic salt and 0.1 to 7 parts by weight of the water-soluble organic liquid are included per 1 part by weight of the organic pigment in the mixture. 6. The colored composition of claim 5, wherein the mixture comprising the organic pigment, the water soluble inorganic salt and the water soluble organic liquid is kneaded at a kneading temperature of 10 to 150 < 0 > C. 6. The colored composition of claim 5, wherein the mixture comprising the organic pigment, the water soluble inorganic salt, and the water soluble organic liquid further comprises a resin. 6. The colored composition of claim 5, wherein the mixture comprising an organic pigment, a water soluble inorganic salt, and a water soluble organic liquid further comprises a pigment derivative. A color filter comprising a filter segment formed of said colored composition as recited in claim 5.

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