JP6532410B2 - Pigment additive, pigment composition, and pigment colorant - Google Patents

Description

  The present invention relates to pigment additives, pigment compositions, and pigment colorants.

  In general, it is difficult to mix and disperse the pigment (particles) in a stable state in a vehicle such as paint, gravure ink, or offset ink. For example, fine pigment particles, once dispersed in a vehicle, tend to aggregate in the vehicle. A vehicle in which pigment particles are aggregated has a problem that its viscosity is increased. In addition, when a vehicle in which aggregated pigment particles are dispersed is used, various problems such as decrease in coloring power of ink and paint and decrease in gloss of a coating film tend to occur.

  By the way, a color filter used to manufacture a liquid crystal color display, an imaging device and the like is manufactured using a pigment dispersion, for example, by the following method. First, a pigment dispersion for a color filter in which pigments of three colors of red (R), green (G) and blue (B) are dispersed in a photosensitive resin solution (pigment colorant for color filter (CF) Prepare). These CF pigment colorants are applied to a color filter substrate by spin coating to form a colored film. Next, after exposing the colored film formed through a photomask, it is developed to pattern the colored film and form desired pixels on the substrate, whereby a color filter can be obtained.

  Pigments for producing color filters include green pigments, red pigments, and blue pigments. As a green pigment, for example, C.I. I. Phthalocyanine greens such as pigment green (hereinafter referred to as "PG") 36, PG7 and PG58 are generally used. Examples of red pigments include C.I. I. Diketopyrrolopyrrole reds such as C.I. pigment red (hereinafter referred to as "PR") 254; anthraquinone reds such as PR 177; azo reds such as PR 242; Moreover, as a blue pigment, for example, C.I. I. Phthalocyanine blue such as pigment blue (hereinafter referred to as "PB") 15: 6 is generally used.

  In addition, since there is a difference between the hue of these pigments and the color characteristics required for the liquid crystal display, complementary color pigments are used in combination. For example, for green and red pigments, C.I. I. Yellow pigments such as C.I. Pigment Yellow (hereinafter referred to as "PY") 138, PY139, PY150 are used in small amounts as complementary pigments. For blue pigments, C.I. I. A small amount of a violet pigment such as pigment violet (hereinafter referred to as "PV") 23 is used as a complementary pigment. Then, in order to form good pixels of the color filter, it is desirable that the main pigment and the complementary color pigment be present uniformly in the CF pigment colorant.

  However, when using a pigment in combination, it is of course difficult to disperse the above pigment in a dispersing medium such as a photosensitive resin liquid using a conventional dispersing machine, and the pigment is not well dispersed. Only dispersion may be obtained. The light transmission of the pixels of the color filter formed using the CF pigment colorant, in which the dispersed state of the pigment is not good, is insufficient, and the light transmission as the pixels of the color filter is insufficient. That is, the pigment colorant for CF obtained by dispersing the pigment using a conventional disperser may not be sufficient as a colorant for forming the pixels of the color filter.

  On the other hand, an acrylic polymer having a high acid value is mainly adopted as a photosensitive resin for a photoresist which is a dispersing medium of a pigment so that the colored film after exposure can be easily developed with an alkaline aqueous solution which is a developer. It is done. However, a pigment colorant containing the above-mentioned pigment and an acrylic polymer having a high acid value has a problem that the pigment is easily aggregated and the viscosity is easily increased. In addition, since aggregation of the pigment progresses with time and the viscosity is increased, there is a problem that the storage stability is low. Furthermore, when it is attempted to manufacture a color filter using a pigment colorant that exhibits a thixotropic viscosity due to its high viscosity or aggregation of the pigment, the central portion of the colored film before exposure may be raised. For this reason, the problem that unevenness and density difference occur in the hue occurs between the pixel located in the central part of the substrate and the pixel located in the peripheral part. And this problem becomes more pronounced when trying to produce a larger screen color filter.

  Therefore, while the pigment colorant for CF (photoresist) contains a pigment in a high concentration, the dispersion state of the pigment in the photosensitive resin which is the dispersion medium of the pigment is good, and the ordinary ordinary drying paint and baking paint It is required to have a low viscosity compared to. In general, even if the pigment concentration is 5 to 20% by mass, the pigment does not aggregate, the viscosity is required to be about 5 to 20 mPa · s, and the storage stability is required to be good.

  In order to satisfy the above requirements, methods of adding a pigment derivative as a pigment dispersant, and methods of treating a pigment with a pigment derivative and using it have been proposed. Specifically, when using phthalocyanine blue such as PB 15: 6 as a pigment, it is proposed to use a substituted derivative of phthalocyanine as a pigment dispersant. When using anthraquinone red such as PR 177 as a pigment, it has been proposed to use a substituted derivative of anthraquinone as a pigment dispersant. Furthermore, when diketopyrrolopyrrole red such as PR254 is used as a pigment, using a substituted derivative of diketopyrrolopyrrole as a pigment dispersant has been proposed (see, for example, Patent Documents 1 to 6).

JP 2002-55224 A JP 2001-240780 A Japanese Patent Application Laid-Open No. 9-272812 Japanese Patent Laid-Open No. 3-26767 Unexamined-Japanese-Patent No. 2004-091497 JP-A-11-189732

  In recent years, there has been a demand to further improve the performance of color filters. Specifically, the brightness of the transmitted light of the colored pixel is increased; the contrast of the transmitted light of the colored pixel is increased; and the reduction of the brightness due to the high temperature treatment of 230 ° C. or more in manufacturing the color filter is suppressed. And so on. However, with conventional techniques as proposed in Patent Documents 1 to 6 and the like, it has been difficult to obtain a pigment colorant capable of producing a color filter satisfying the above-mentioned performance. Furthermore, pigment colorants obtained by the prior art are not limited to those for color filters, and foreign substances may be generated in the coating film (colored film) to be formed, so improvement is required.

  The present invention has been made in view of the problems of the prior art as described above, and it is possible to significantly improve the flowability of the pigment-containing ink, paint, etc. It is possible to prevent aggregation of particles, to prevent generation of foreign matter, to exhibit excellent gloss and sharpness, and to manufacture a colored article whose luminance is not easily reduced even by high-temperature treatment at 230 ° C. or more at the time of color filter production. It is to provide possible pigment additives. Another object of the present invention is to provide a pigment composition and a pigment colorant obtained by using the above-mentioned pigment additive.

That is, according to the present invention, the pigment additive shown below is provided.
[1] A pigment additive which is a compound represented by the following general formula (1).

（前記一般式（１）中、Ｄは、下記式（２）〜（１０）のいずれかで表される基であり、Ｒは、単結合又は炭素数１〜４の直鎖状のアルキレン基を示し、ｎは１〜４の数を示す）

(In the general formula (1), D is a group represented by any one of the following formulas (2) to (10) , R is a single bond or a linear alkylene group having 1 to 4 carbon atoms And n represents a number from 1 to 4)

（前記式（２）〜（１０）中、＊は、前記一般式（１）中の−ＮＨとの結合位置を示す。前記式（２）中、Ｒ₁は、単結合、メチレン基、又は下記式（Ｉ）で表される２価の基を示し、前記式（５）中、Ｒ₂は、それぞれ独立に、水素原子又はフェニル基を示し、前記式（５）中のＲ₃、前記式（６）中のＲ₄、及び前記式（８）中のＲ₅は、メチレン基又は下記式（Ｉ）で表される２価の基を示し、前記式（９）中、Ｘは、それぞれ独立に、水素原子又はハロゲンを示す）

(In the formulas (2) to (10), * represents a bonding position to -NH in the general formula (1). In the formula (2), R ₁ represents a single bond, a methylene group, or A divalent group represented by the following formula (I) is shown, and in the formula (5), each R ₂ independently represents a hydrogen atom or a phenyl group, and R ₃ in the formula (5), R ₄ in the formula (6) and R ₅ in the formula (8) represent a methylene group or a divalent group represented by the following formula (I), and in the formula (9), X represents Each independently represents a hydrogen atom or a halogen)

Further, according to the present invention, a pigment composition shown below is provided.
[ 2 ] A pigment composition containing a pigment and the pigment additive according to the above [1 ] .
[ 3 ] The pigment composition according to the above [ 2 ], wherein the blending amount of the pigment additive is 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment.
[ 4 ] Furthermore, a pigment derivative is contained as a pigment dispersant, and the pigment derivative is at least one of a sulfonic acid pigment derivative and a sulfonamide pigment derivative as described in [ 2 ] or [ 3 ]. Pigment composition.
[ 5 ] The compounding amount of the pigment derivative is 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment, and the compounding amount of the pigment derivative is 10 to 200 parts by mass with respect to 100 parts by mass of the pigment additive The pigment composition as described in said [ 4 ] which is it.

Further, according to the present invention, the pigment colorants shown below are provided.
[ 6 ] A pigment colorant containing the pigment composition according to any one of the above [ 2 ] to [ 5 ] and a film forming material.
[ 7 ] The pigment colorant according to the above [ 6 ], which is for image display, image recording, for printing ink, for writing ink, for plastics, for pigment printing, or for paints.
[ 8 ] The pigment colorant according to [ 6 ], which is for color filters.

  The pigment additive of the present invention can significantly improve the flowability of the pigment-containing ink, paint, etc., and can prevent the particle aggregation of the pigment, and can prevent the generation of foreign matter while having excellent gloss and It is possible to produce a colored article which exhibits sharpness and whose luminance is unlikely to be reduced even by high-temperature treatment at 230 ° C. or higher when producing a color filter. For this reason, the pigment additive of the present invention includes printing inks such as offset inks and gravure inks, various paints, plastics, pigment printing agents, dry or liquid toners for electrophotography, inks for inkjet recording, inks for thermal transfer recording, color filters It can be suitably used for vehicles used for resists, inks for writing instruments, etc. In addition, when the pigment additive of the present invention is used, a pigment composition capable of remarkably improving the flowability of various paints and the like, preventing pigment particle aggregation, and forming a colored film in which the generation of foreign matter is effectively prevented. And pigment colorants can be provided. Furthermore, the pigment colorant of the present invention can produce a colored product having excellent gloss and sharpness, as well as being resistant to thickening and gelation during storage. In particular, even when processing is performed at a high temperature of 230 ° C. or higher, the luminance is unlikely to be reduced, and a colored product with high luminance can be manufactured. For this reason, the pigment colorant of the present invention is particularly suitable as a pigment colorant for color filters and the like.

<Pigment additive>
Hereinafter, the present invention will be described in detail by way of examples of preferred embodiments. One of the main features of the pigment additive of the present invention is that it is a compound represented by the following general formula (1). The pigment additive of the present invention having such characteristics has excellent affinity to various pigments, whether organic or inorganic. In addition, by using a pigment colorant compounded with the pigment additive of the present invention, a color filter having excellent brightness and sharpness can be suppressed even when treated at high temperatures of 230 ° C. or higher, for example. Etc. can be produced. For this reason, the pigment additive of the present invention can be used as a material for preparing pigment colorants for various applications.

（前記一般式（１）中、Ｄ−ＮＨ−は、アミノ基を有する有機色素に由来する構造部分を示し、Ｒは、単結合又は炭素数１〜４の直鎖状のアルキレン基を示し、ｎは１〜４の数を示す）

(In the above general formula (1), D-NH- represents a structural moiety derived from an organic dye having an amino group, R represents a single bond or a linear alkylene group having 1 to 4 carbon atoms, n represents a number of 1 to 4)

  Even when using a pigment colorant blended with additives such as a commercially available antioxidant, when it is treated at a high temperature of 230 ° C. or higher, the luminance of the resulting colored product tends to be reduced. This is because general additives such as antioxidants are low molecular weight compounds, and it becomes difficult to stay in the vicinity of the pigment due to bleed out, extraction, and diffusion into the dispersing medium, etc. It is considered that this is because the effect of the additive is insufficient. On the other hand, the pigment additive of the present invention is a relatively high molecular weight compound having a structure in which a hindered phenol group is introduced into a matrix of an organic dye. For this reason, while being easy to adsorb | suck to the surface of a pigment particle, the antioxidant ability of a hindered phenol group is exhibited. As a result, while preventing aggregation of pigment particles and the generation of foreign substances, it is possible to suppress a decrease in luminance even when treated at a high temperature of 230 ° C. or higher, a color filter having excellent gloss and sharpness, etc. Can be produced.

  In general formula (1), D-NH- represents a structural moiety derived from an organic dye having an amino group. As the organic dye having an amino group, generally commercially available pigments or dyes can be used. Organic dyes having an amino group include phthalocyanine dyes, diketopyrrolopyrrole dyes, quinacridone dyes, anthraquinone dyes, perylene dyes, monoazo dyes, disazo dyes, condensed azo dyes, quinophthalone dyes, etc. And pigments and dyes of

  Further, as the organic dye having an amino group, an organic dye in which an aminomethyl group or an aminophthalimidomethyl group is introduced to a dye such as the above-described pigment and dye can also be used. The organic dye into which an aminomethyl group is introduced can be synthesized, for example, by hydrolyzing an organic dye into which a phthalimidomethyl group is introduced by a known method. In addition, organic dyes having an amino group produced by various methods can be used.

  Specific examples of the organic dye having an amino group include tetraamino phthalocyanine, monosubstituted (or 2 to 4 substituted) aminomethyl phthalocyanine, monosubstituted (or 2 to 4 substituted) 4-aminophthalimido methyl phthalocyanine, 2,2′- Diamino-1,1'-bianthraquinone, 4,4'-diamino-1,1'-bianthraquinone, 1-aminoanthraquinone, 2-aminoanthraquinone, 1-amino-4-hydroxyanthraquinone, 2-amino-3- Hydroxyanthraquinone, 1-amino-2-methylanthraquinone, 1,4-diaminoanthraquinone, 1,5-diaminoanthraquinone, 1,4-diamino-2,3-dicyano-9,10-anthraquinone, 1,4-diamino- 2,3-Dichloroanthraquinone, 1,5-diamino-4,8-diphenyl Roxyanthraquinone, 2,6-diaminoanthraquinone, monosubstituted (or 2 to 4 substituted) aminomethyl diketopyrrolopyrrole (eg, PR254, PR255, PR272, PR264, PO71, PO73, etc.), monosubstituted (or 2 to 4 substituted) ) 4-Aminophthalimidomethyl diketopyrrolopyrrole (eg, PR254, PR255, PR272, PR264, PO71, PO73, etc.), monosubstituted (or 2-4 substituted) aminomethyl quinacridone (eg, PV19, PR122, PR202, PR209, etc.) ), 1-substituted (or 2 to 4 substituted) 4-aminophthalimidomethyl quinacridone (for example, PV19, PR122, PR202, PR209, etc.), N, N '-(1,4-phenylene) bis [4-[(4- (4) Methaneaminophenyl) azo] 3-hydroxy-2-naphthalenecarboxamide], N, N '-(2,5-dichloro-1,4-phenylene) bis [4-[(4-methaneaminophenyl) azo] -3-hydroxy-2- Naphthalenecarboxamide], N, N'-bis (2-aminophenyl) -3,4,9,10-perylene bis (dicarbimide), N, N'-bis (3-aminophenyl) -3,4,9, 10-perylene bis (dicarboimide), N, N′-bis (4-aminophenyl) -3,4,9,10-perylene bis (dicarboimide), 2- (8-aminoquinolin-2-yl) -1H-indene 1,3 (2H) -dione, 2- (8-aminoquinolin-2-yl) -4,5,6,7-tetrachloro-1H-indene-1,3 (2H) -dione, 2- (8) -Aminoquinoline- 2-yl) -4,5,6,7-tetrabromo-1H-indene-1,3 (2H) -dione, 5-((6-aminomethyl-2,4-dihydroxyquinolin-3-yl) diazenyl) -1H-benzo [d] imidazol-2 (3H) -one, 5-((7-aminomethyl-2,4-dihydroxyquinolin-3-yl) diazenyl) -1H-benzo [d] imidazol-2 (3H) ) -One, 5-amino-2-((2,4-dihydroxy-3-((2-oxo-2,3-dihydro-1H-benzo [d] imidazol-5-yl) diazenyl) quinoline-7-) (I)) methyl) isoindoline-1,3-dione, 5-amino-2-((2,4-dihydroxy-3-((2-oxo-2,3-dihydro-1H-benzo [d] imidazole-5) -Yl) diazenyl) quino Such as down-6-yl) methyl) isoindoline-1,3-dione can be cited.

  It is preferable that D in General formula (1) is group represented by either of following formula (2)-(10).

（前記式（２）〜（１０）中、＊は、前記一般式（１）中の−ＮＨとの結合位置を示す。前記式（２）中、Ｒ₁は、単結合、メチレン基、又は下記式（Ｉ）で表される２価の基を示し、前記式（５）中、Ｒ₂は、それぞれ独立に、水素原子又はフェニル基を示し、前記式（５）中のＲ₃、前記式（６）中のＲ₄、及び前記式（８）中のＲ₅は、メチレン基又は下記式（Ｉ）で表される２価の基を示し、前記式（９）中、Ｘは、それぞれ独立に、水素原子又はハロゲンを示す）

(In the formulas (2) to (10), * represents a bonding position to -NH in the general formula (1). In the formula (2), R ₁ represents a single bond, a methylene group, or A divalent group represented by the following formula (I) is shown, and in the formula (5), each R ₂ independently represents a hydrogen atom or a phenyl group, and R ₃ in the formula (5), R ₄ in the formula (6) and R ₅ in the formula (8) represent a methylene group or a divalent group represented by the following formula (I), and in the formula (9), X represents Each independently represents a hydrogen atom or a halogen)

  The pigment additive of the present invention exhibits excellent action as a pigment additive even in a small amount. In addition, the pigment composition and the pigment colorant prepared using the pigment additive of the present invention are less likely to cause thickening or gelation during storage, and foreign matter is generated in the coating film formed using them. Hateful. As a specific example of the pigment additive of this invention, the compound etc. which are represented by following formula (A)-(H) can be mentioned.

  As a further specific example of the pigment additive of this invention, the compound etc. which are represented by following formula (1-1)-(1-8) can be mentioned.

  The compound (pigment additive) represented by the general formula (1) is, for example, 3- (3,5-di-tert-butyl-4-hydroxybenzene) in an organic dye having an amino group such as tetraamino phthalocyanine. It can be synthesized by reacting an acid chloride having a hindered phenol group such as propionic acid chloride. In addition, the acid chloride which has a hindered phenol group can be synthesize | combined from the carboxylic acid compound which has a hindered phenol group, for example. The pigment additive of the present invention may contain a small amount of unreacted raw material, but as long as the effects of the present invention can be obtained, some of the unreacted raw material may be contained.

  As a carboxylic acid compound having a hindered phenol group, 3,5-di-tert-butyl-4-hydroxybenzoic acid, 2- (3,5-di-tert-butyl-4-hydroxyphenyl) acetic acid, 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, 4- (3,5-di-tert-butyl-4-hydroxyphenyl) butanoic acid, 5- (3,5-di-tert) And -butyl-4-hydroxyphenyl) pentanoic acid and the like can be mentioned. Among them, 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid is preferable.

Although the method of using the pigment additive of the present invention is not particularly limited, the following methods of use are exemplified. With any method, it is possible to obtain the effect as the target pigment addition.
(1) The pigment and the pigment additive are mixed in advance by a known method, and the obtained pigment composition is added to a vehicle or the like to disperse the pigment in the vehicle.
(2) The pigment and the pigment additive are separately added to the vehicle or the like at a predetermined ratio to disperse the pigment in the vehicle.
(3) After separately dispersing the pigment and the pigment additive in a vehicle or the like, the obtained dispersions are mixed at a predetermined ratio, and the pigment is dispersed in the vehicle.
(4) A pigment additive is added at a predetermined ratio to a dispersion obtained by dispersing a pigment in a vehicle or the like to disperse the pigment in the vehicle.

<Pigment composition>
The pigment composition of the present invention contains a pigment and the above-mentioned pigment additive. It is preferable that the compounding quantity of the pigment additive with respect to 100 mass parts of pigments is 0.5-40 mass parts, and it is further more preferable that it is 1-20 mass parts. If the blending amount of the pigment additive is smaller than the above range, the effects of the intended additive may not be sufficiently obtained. On the other hand, if the blending amount of the pigment additive is larger than the above range, the effect of the additive becomes flat and no further effect can be expected, and the cost of the material is increased, which is disadvantageous in productivity. May be Furthermore, in a paint or ink using a pigment composition containing such a pigment additive in excess, various physical properties of the vehicle are lowered, or the color of the pigment is largely changed by the color of the pigment additive itself. Sometimes.

  The pigment composition of the present invention may further contain a pigment derivative as a pigment dispersant. The pigment derivative is preferably at least one of a sulfonic acid pigment derivative and a sulfonamide pigment derivative. If the hue of the pigment colorant to be prepared is blue, it is preferable to use a sulfonated product or a sulfonated product of phthalocyanine as a pigment derivative. In addition, when the color of the pigment colorant is red, it is preferable to use sulfonated or sulfonated diketopyrrolopyrrole; sulfonated or sulfonated quinacridone; and sulfonated or sulfonated anthraquinone as a pigment derivative. Is preferred. Furthermore, when the color of the pigment colorant is yellow, it is preferable to use a sulfonated or sulfonidated product of PY138 as a pigment derivative.

  The compounding amount of the pigment derivative is preferably 0.5 to 40 parts by mass, and more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the pigment. When the blending amount of the pigment derivative is smaller than the above range, the effect as a target pigment dispersant may not be sufficiently obtained. On the other hand, if the blending amount of the pigment derivative is larger than the above-mentioned range, the effect of the pigment dispersant becomes flat, and no further effect can be expected, and the cost of the material is increased. May be Furthermore, in a paint or ink using a pigment composition containing such a pigment derivative in excess, various physical properties of the vehicle decrease, or the color of the pigment largely changes depending on the color of the pigment derivative itself. In some cases.

  Moreover, it is preferable that it is 10-200 mass parts with respect to 100 mass parts of pigment additives, and, as for the compounding quantity of a pigment derivative, it is more preferable that it is 20-100 mass parts. If the blending amount of the pigment derivative is less than the above range, the blending amount of the pigment additive is large, and the effect of the pigment derivative as a pigment dispersant is not sufficiently obtained, and a target low viscosity dispersion liquid is obtained. It may not be obtained. On the other hand, if the blending amount of the pigment derivative is larger than the above range, the blending amount of the pigment additive may be reduced, and the effect of the added pigment additive may not be sufficiently obtained.

  Specific examples of the pigment from which an effective additive effect can be obtained by using the pigment additive of the present invention include soluble and insoluble azo pigments, high molecular weight azo pigments, phthalocyanine pigments, quinacridone pigments, anthraquinone pigments and diketopyrrolo. Pyrrole pigments, quinophthalone pigments, methine / azomethine pigments, perylene pigments, perinone pigments, isoindolinone pigments, isoindoline pigments, metal complex pigments and the like can be mentioned.

The method for producing the pigment composition of the present invention is not particularly limited. For example, the pigment composition of the present invention can be obtained by mixing a pigment and a pigment additive by a conventionally known method. In addition, the method of (1)-(4) shown below can be mentioned as a specific example of the method of manufacturing the pigment composition of this invention.
(1) A method of mixing powder of pigment and powder of pigment additive without using a dispersing machine.
(2) A method of mechanically mixing a pigment and a pigment additive with various dispersers such as a kneader, a roll, an attritor, a horizontal bead mill and the like.
(3) A method of uniformly depositing the pigment additive on the surface of the pigment by adding and mixing a solution in which the pigment additive is dissolved or finely dispersed in a suspension of the aqueous or organic solvent system of the pigment.
(4) A method in which a pigment and a pigment additive are dissolved in a solvent having a strong dissolving power such as sulfuric acid and then coprecipitated with a poor solvent such as water.

  The nature of the pigment additive used to prepare the pigment composition may be any of solution, slurry, paste and powder. Even when pigment additives of any nature are used, desired effects can be obtained.

<Pigment coloring agent>
The pigment colorant of the present invention contains the above-mentioned pigment composition and a film-forming material. The pigment colorant of the present invention mixes, for example, the above-described finely divided pigment composition with a film-forming material such as a resin ((co) polymer), an oligomer, or a monomer selected according to the application. It can be obtained by The pigment colorant of the present invention can be used in a wide range of fields as a colorant for image display, image recording, printing ink, writing ink, plastic, pigment printing, paint and the like. In particular, as an image display material in which the transparency of colored pixels is a problem, it is particularly suitable as a pigment colorant for color filters. Of course, the pigment colorant of the present invention is also useful as a material for an image recording agent such as a dry or liquid toner for electrophotography, an ink for inkjet recording, an electrodeposition recording liquid, an ink for thermal transfer recording, and an ink for writing instruments. The materials for these image recording agents are used in various image recording methods such as an inkjet recording method, an electrodeposition recording method, and an electrophotographic method. By using the pigment colorant of the present invention, it is possible to prepare a material for an image recording agent which can provide high quality images by any image recording method.

  Hereinafter, further details of the pigment colorant of the present invention will be described by taking a pigment dispersion for color filter (pigment colorant for color filter (CF)) which is a pigment colorant for image display as a representative example. In order to prepare a pigment dispersion (photoresist) for a color filter, first, the above-described pigment composition is added to a solution containing a film-forming material and premixed. Then, dispersion treatment can be performed to obtain a pigment dispersion for color filter. More specifically, adding and mixing a pigment composition, which has been uniformly ground using a dispersing machine such as a vertical medium disperser, a horizontal medium disperser or a ball mill, to a liquid containing a film-forming material Thus, a pigment dispersion for color filter can be obtained. In addition, a solution obtained by dissolving a pigment and a pigment additive in sulfuric acid or the like is mixed with water to precipitate and separate a pigment composition containing the pigment and the pigment additive as a solid solution or a co-precipitate. Even if the separated pigment composition is added to and mixed with a liquid containing a film-forming material, a polymer dispersant and the like, then grinding and dispersion may be carried out using a horizontal type wet medium disperser (bead mill) such as Dyno mill, A pigment dispersion for color filter can be obtained.

  The pigment colorant of the present invention may further contain a polymeric dispersant. In addition, if the surface of the pigment in the pigment colorant is treated with an acidic pigment derivative such as a sulfonic acid-based pigment derivative, it is preferable to further contain a basic polymer dispersant. On the other hand, if the surface of the pigment in the pigment colorant is treated with a basic pigment derivative such as a sulfonamide type pigment derivative, it is preferable to further contain an acidic polymer dispersant. By further containing a polymer dispersant, a pigment dispersion for a color filter with lower viscosity and high contrast can be obtained.

  Known basic dispersants can be used as the basic polymer dispersant. Specific examples of the basic polymer dispersant include the following trade names: DISPERBYK-160, 161, 162, 163, 164, 166, 171, 182, 184, 2000, and the like. 2001, 2070, 2150 (above, made by Bick Chemie): EFKA-44, 46, 47, 48, 4010, 4015, 4020, 4050, 4055, 4060, 4300, 4330, 4400, 4406, 4510, 4800 (above, made by BASF Corporation); SOLSPERS-24000, 32550, NBZ-4204 / 10 (above, made by Lubrizol company); Hinoact T-6000, No. 7000, Same as 8000 (above, manufactured by Kawaken Fine Chemical Co., Ltd.); Addisper PB-821, 822, 823 ( On, it can be mentioned manufactured by Ajinomoto Fine-Techno Co., Inc.), and the like.

  A well-known dispersing agent can be used as an acidic polymer dispersing agent. Specific examples of the acidic polymer dispersant include, under the following trade names, KF-10000 (manufactured by Kawaken Fine Chemical Co., Ltd.); Alpha Resin SA-300 (manufactured by Alpha Kaken); DISPERBYK-110, 111, and 180 (Hereinafter, products made by Big Chemie Co., Ltd.); SOLSPERS-41000 (made by Lubrizol company); Addisper PA-111 (made by Ajinomoto Fine Techno Co., Ltd.) and the like can be mentioned.

  The compounding amount of the polymer dispersant is preferably 2 to 100 parts by mass, and more preferably 10 to 50 parts by mass with respect to 100 parts by mass of the pigment. When the blending amount of the polymer dispersant is less than 2 parts by mass, it may be difficult to obtain good pigment dispersion stability. On the other hand, if the blending amount of the polymer dispersant is more than 100 parts by mass, the developability of the formed film may be reduced.

  As a liquid containing a film-forming material used to prepare a pigment dispersion for color filter, a solution of a film-forming polymer contained in a conventionally known pigment dispersion for color filter can be used. Moreover, as a liquid medium used for the liquid containing a film formation material, the liquid mixture of an organic solvent, water, and an organic solvent and water etc. can be mentioned. If necessary, conventionally known additives such as a dispersion aid, a leveling agent, and an adhesion agent can be added to the pigment dispersion for color filter.

  The amount of the pigment composition contained in the pigment colorant of the present invention is preferably 5 to 500 parts by mass, and more preferably 50 to 250 parts by mass with respect to 100 parts by mass of the film-forming material. Further, as the solution containing the film-forming material, a solution containing a photosensitive film-forming material or a solution containing a non-photosensitive film-forming material can be appropriately selected and used according to the application. As a specific example of the liquid containing a photosensitive film formation material, a liquid containing a photosensitive film formation material used for an ultraviolet curable ink, an electron beam curable ink, etc. can be mentioned. Further, specific examples of the liquid containing the non-photosensitive film-forming material include varnishes used for printing inks such as letterpress inks, lithographic inks, gravure inks, screen inks, etc. varnishes used for normal temperature drying or baking paints; Examples include varnishes used for coating and varnishes used for thermal transfer ribbons.

  The pigment dispersion for color filter is required to have a good dispersion state of the pigment while containing a pigment at a high concentration, and to have a low viscosity as compared with a general air-drying paint or baking paint. Generally, even when the pigment concentration is 5 to 20% by mass, the pigment does not aggregate, the viscosity is about 5 to 20 mPa · s, and the storage stability is required to be good. Therefore, in the case of using for a color filter, it is preferable that the pigment dispersion of the present invention satisfy the above-mentioned viscosity condition. Preferably, the viscosity is 5 to 15 mPa · s, and the viscosity increase rate after leaving for 1 month at 25 ° C. (after leaving) is within 10%. When the viscosity increases, it becomes difficult to form a film with a constant film thickness.

  Specific examples of the photosensitive film-forming material include photosensitive cyclic rubber resin, photosensitive phenolic resin, photosensitive polyacrylate resin, photosensitive polyamide resin, photosensitive polyimide resin, unsaturated polyester resin And photosensitive resins such as polyester acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, and polyol acrylate resins. In addition, you may add various monomers as a reactive diluent to the liquid containing these photosensitive resin.

  A photocurable photosensitive pigment dispersion is obtained by adding a photopolymerization initiator such as benzoin ether or benzophenone to a pigment colorant containing a photosensitive resin as a film-forming material, and milling it by a conventionally known method. be able to. If a thermal polymerization initiator is used instead of the above-mentioned photopolymerization initiator, a thermosetting pigment dispersion can be obtained.

  On the other hand, specific examples of the non-photosensitive film-forming material include styrene- (meth) acrylate (co) polymer, soluble polyamide resin, soluble polyimide resin, soluble polyamideimide resin, soluble polyesterimide resin Resin, water-soluble salt of styrene-maleic acid ester copolymer, water-soluble salt of (meth) acrylic acid ester- (meth) acrylic acid copolymer, resin such as water-soluble amino polyester resin, and water-soluble resin Salt can be mentioned.

  Next, the present invention will be more specifically described by way of examples and comparative examples. Hereinafter, “parts” and “%” are on a mass basis unless otherwise specified.

<Preparation of pigment additive>
Example 1
To 70 parts of dimethylacetamide, 13.9 parts of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid and 6.5 parts of thionyl chloride are added, and the reaction is continued at 40 to 50 ° C. for 0.5 hours. It stirred. 8.3 parts of tetraamino phthalocyanines obtained by reduce | restoring tetranitro phthalocyanine were added, and it stirred at 120-130 degreeC for 3 hours. The mixture was allowed to cool, then poured into 700 parts of water, filtered, washed with water, and dried to obtain 20.3 parts of a blue pigment additive (A) represented by the following formula (A).

(Example 2)
A red pigment additive (B) represented by the following formula (B) in the same manner as Example 1 described above except that 11.1 parts of PR177 was used instead of 8.3 parts of tetraamino phthalocyanine. 22.9 parts were obtained.

(Example 3)
In the same manner as in Example 1 described above, except that 23.1 parts of PR255 in which about one 4-aminophthalimidomethyl group was introduced in one molecule instead of 8.3 parts of tetraamino phthalocyanine were used. 34.2 parts of a red pigment additive (C) represented by the following formula (C) was obtained.

(Example 4)
In the same manner as in Example 1 described above, except that 24.3 parts of PV 19 in which about one 4-aminophthalimidomethyl group was introduced in one molecule were used instead of 8.3 parts of tetraamino phthalocyanine. 35.3 parts of a red pigment additive (D) represented by the following formula (D) was obtained.

(Example 5)
To 30 parts of dimethylacetamide, 5.6 parts of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid and 2.6 parts of thionyl chloride are added, and the reaction is continued at 40 to 50 ° C. for 0.5 hours. It stirred. Three parts of 4'-aminoacetanilide were added and stirred for 3 hours at 90 to 100 ° C, then 30 parts of water and 8.3 parts of concentrated hydrochloric acid were added and stirred at 90 to 100 ° C for one hour. The mixture was cooled to 0 to 10 ° C., and 1.4 parts of sodium nitrite was added to diazotize. In 150 parts of water, 5 parts of sodium hydroxide and 4.5 parts of N, N '-(1,4-phenylene) bis (3-hydroxynaphthalene-2-carboxamide) are dissolved, and the above-mentioned diazo solution is charged. The mixture was stirred at -30 ° C for 4 hours and then at 70-80 ° C for 1 hour. Filtration, washing with water and drying gave 11.6 parts of a red pigment additive (E) represented by the following formula (E).

(Example 6)
A compound in which about one aminophthalimidomethyl group is introduced into one molecule of a compound in which 5-aminobenzimidazolinone is diazotized to 2,4-dihydroxyquinoline instead of 8.3 parts of tetraamino phthalocyanine In the same manner as in Example 1 described above except that 24.7 parts were used, 35.7 parts of a red pigment additive (F) represented by the following Formula (F) was obtained.

(Example 7)
8-amino-2- (4,5,6,7-tetrachloro-1,3-dioxo-2,3) obtained by hydrolyzing PY138 with 95% sulfuric acid instead of 8.3 parts of tetraamino phthalocyanine Yellow pigment additive (G) 36 represented by the following formula (G) in the same manner as in Example 1 except that 25.3 parts of -dihydro-1H-inden-2-yl) was used I got .5 copies.

(Example 8)
To 30 parts of dimethylacetamide, 5.6 parts of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid and 2.6 parts of thionyl chloride are added, and the reaction is continued at 40 to 50 ° C. for 0.5 hours. It stirred. Three parts of 4'-aminoacetanilide were added and stirred for 3 hours at 90 to 100 ° C, then 30 parts of water and 8.3 parts of concentrated hydrochloric acid were added and stirred at 90 to 100 ° C for one hour. The mixture was cooled to 0 to 10 ° C., and 1.4 parts of sodium nitrite was added to diazotize. In 150 parts of water, 5 parts of sodium hydroxide and 4.7 parts of 5- (acetoacetamido) -2-benzoimidazolinone are dissolved, and the above-mentioned diazo solution is charged, followed by 4 hours at 20-30 ° C., and then 70-80. Stir for 1 hour at ° C. Filtration, water washing and drying gave 11.6 parts of a yellow pigment additive (H) represented by the following formula (H).

When mass spectrometry by MALDI (abbreviation of matrix assisted laser desorption ionization method) was performed for each compound (pigment additive) obtained in Examples 1 to 8, peaks corresponding to the following molecular weights were detected. From the raw materials used and the results of mass analysis, it was confirmed that the compound (pigment additive) of the target composition was obtained.
Pigment additive (A): Molecular weight 1709.75
Pigment additive (B): Molecular weight 965.21
-Pigment additive (C): Molecular weight 722.85
-Pigment additive (D): Molecular weight 746.87
Pigment additive (E): molecular weight 1207.50
Pigment additive (F): molecular weight 755.84
Pigment additive (G): Molecular weight 686.47
Pigment additive (H): molecular weight 612.74

<Preparation of Pigment Compositions (1) to (16)>
(Example 9)
100 parts of α-type copper phthalocyanine blue pigment (trade name "CHROMOFINE BLUE 5187", manufactured by Dainichi Seika Kogyo Co., Ltd., PB 15: 6), 5 parts of the pigment additive (A) obtained in Example 1, pigment dispersant (I) Three parts of (phthalocyanine sulfonate (trade name "SOLSPERS-12000", manufactured by Lubrizol)), 600 parts of sodium chloride having an average particle diameter of 5 μm, and 150 parts of diethylene glycol were charged in a kneader equipped with a pressure lid. After pre-kneading until uniform wet mass was produced in the kneader, the pressure lid was closed and kneading and grinding were started while holding down the contents at a pressure of 6 kg / cm ² . The mixture was milled and ground for 4 hours while controlling the cooling temperature and the amount of cooling water so that the temperature of the contents was 40 to 45 ° C. to obtain a ground material. The resulting milled product was poured into 5,000 parts of a 2% aqueous sulfuric acid solution heated to 80 ° C., stirred for 1 hour, filtered and washed with water to remove sodium chloride and diethylene glycol. The filter residue was dried in a hot air drier at 80 ° C. for 24 hours to obtain a pigment composition (1).

(Example 10)
A pigment dispersant (J) represented by the following formula (J) described in Patent Document 1 was used in place of the pigment dispersant (I). Furthermore, it replaced with 2% sulfuric acid aqueous solution, and used 2% sodium hydroxide aqueous solution. A pigment composition (2) was obtained in the same manner as in Example 9 except for the above.

(Example 11)
In place of the α-type copper phthalocyanine blue pigment, PR177 (trade name “PALIOGEN RED L4039”, manufactured by BASF AG) was used. In addition, the pigment additive (B) obtained in Example 2 is used in place of the pigment additive (A), and further, in place of the pigment dispersant (I), the following formula described in Patent Document 2 The pigment dispersant (K) represented by K) was used. A pigment composition (3) was obtained in the same manner as in Example 9 except for the above.

(Example 12)
In place of the pigment dispersant (K), a pigment dispersant (L) represented by the following formula (L) described in Patent Document 3 was used. Furthermore, it replaced with 2% sulfuric acid aqueous solution, and used 2% sodium hydroxide aqueous solution. A pigment composition (4) was obtained in the same manner as in Example 11 except for the above.

(Example 13)
Instead of the α-type copper phthalocyanine blue pigment, PR254 (trade name “IRGAZIN RED L3660HD”, manufactured by BASF) was used. Further, the pigment additive (C) obtained in Example 3 was used in place of the pigment additive (A). Furthermore, in place of the pigment dispersant (I), a pigment dispersant (M) represented by the following formula (M) described in Patent Document 2 was used. A pigment composition (5) was obtained in the same manner as in Example 9 except for the above.

(Example 14)
A pigment dispersant (N) represented by the following formula (N) described in Patent Document 4 was used in place of the pigment dispersant (M). Furthermore, it replaced with 2% sulfuric acid aqueous solution, and used 2% sodium hydroxide aqueous solution. A pigment composition (6) was obtained in the same manner as in Example 13 except for the above.

(Example 15)
A pigment composition (7) was obtained in the same manner as in Example 13 except that the pigment additive (D) obtained in Example 4 was used instead of the pigment additive (C).

(Example 16)
A pigment composition (8) was obtained in the same manner as in Example 14 described above except that the pigment additive (D) obtained in Example 4 was used instead of the pigment additive (C).

(Example 17)
A pigment composition (9) was obtained in the same manner as in Example 13 except that the pigment additive (E) obtained in Example 5 was used instead of the pigment additive (C).

(Example 18)
A pigment composition (10) was obtained in the same manner as in Example 14 except that the pigment additive (E) obtained in Example 5 was used instead of the pigment additive (C).

(Example 19)
A pigment composition (11) was obtained in the same manner as in Example 13 except that the pigment additive (F) obtained in Example 6 was used instead of the pigment additive (C).

Example 20
A pigment composition (12) was obtained in the same manner as in Example 14 described above, except that the pigment additive (F) obtained in Example 6 was used instead of the pigment additive (C).

(Example 21)
PY138 (trade name "Paliotol Yellow L0960HD", manufactured by BASF Corp.) was used in place of the α-type copper phthalocyanine blue pigment. In addition, the pigment additive (G) obtained in Example 7 was used in place of the pigment additive (A). Furthermore, in place of the pigment dispersant (I), a pigment dispersant (O) represented by the following formula (O) described in Patent Document 5 was used. A pigment composition (13) was obtained in the same manner as in Example 9 except for the above.

(Example 22)
In place of the pigment dispersant (O), a pigment dispersant (P) represented by the following formula (P) described in Patent Document 6 was used. Furthermore, it replaced with 2% sulfuric acid aqueous solution, and used 2% sodium hydroxide aqueous solution. A pigment composition (14) was obtained in the same manner as in Example 21 except for the above.

(Example 23)
A pigment composition (15) was obtained in the same manner as in Example 21 except that the pigment additive (H) obtained in Example 8 was used instead of the pigment additive (G).

(Example 24)
A pigment composition (16) was obtained in the same manner as in Example 22 except that the pigment additive (H) obtained in Example 8 was used instead of the pigment additive (G).

  The combinations of pigments, pigment additives and pigment dispersants used in preparing the pigment compositions (1) to (16) are shown in Table 1.

<Preparation of Pigment Dispersion (Pigment Colorant for Color Filter (CF))>
(Example 25)
An acrylic resin varnish having an average molecular weight of 12,000 and a solid content concentration of 40%, obtained by copolymerizing methacrylic acid / benzyl acrylate / styrene / hydroxyl acrylate at a molar ratio of 25/50/15/10 The pigment dispersion was prepared according to the method described below. 50 parts of the above acrylic resin varnish, 20 parts of the pigment composition (1), 17.4 parts of a basic polymer dispersant (trade name "DISPERBYK-2001" manufactured by BIC Chemie, 46% solid content), and a solvent Twenty parts of propylene glycol-1-monomethyl ether-2-acetate were mixed and premixed, followed by dispersion using a horizontal bead mill to obtain a pigment colorant for CF (Example 25).

(Example 26)
The pigment composition (2) was used in place of the pigment composition (1). Furthermore, in place of the basic polymer dispersant, 15.4 parts of an acidic polymer pigment dispersant (trade name “DISPERBYK-110”, manufactured by Bick Chemie, solid content 52%) was used. A pigment colorant for CF (Example 26) was obtained in the same manner as Example 25 described above, except for these.

(Examples 27, 29, 31, 33, 35, 37, 39)
In the above, except that the pigment composition (3), (5), (7), (9), (11), (13) and (15) is used instead of the pigment composition (1), respectively A pigment colorant for CF (Examples 27, 29, 31, 33, 35, 37, 39) was obtained in the same manner as in Example 25.

(Examples 28, 30, 32, 34, 36, 38, 40)
In the above, except that the pigment composition (4), (6), (8), (10), (12), (14) and (16) is used instead of the pigment composition (2), respectively A pigment colorant for CF (Examples 28, 30, 32, 34, 36, 38, 40) was obtained in the same manner as in Example 26.

(Comparative example 1)
A composition containing PB 15: 6 not treated with a pigment additive was obtained in the same manner as in Example 9 described above except that the pigment additive (A) was not used. Then, a pigment colorant for CF (Comparative Example 1) was obtained in the same manner as Example 25 described above, except that the composition obtained above was used instead of the pigment composition (1).

(Comparative example 2)
A composition containing PB 15: 6 not treated with a pigment additive was obtained in the same manner as Example 10 described above except that the pigment additive (A) was not used. Then, a pigment colorant for CF (Comparative Example 2) was obtained in the same manner as Example 26 described above except that the composition obtained above was used instead of the pigment composition (2).

(Comparative example 3)
A composition containing PR177 not treated with a pigment additive was obtained in the same manner as in Example 11 described above except that the pigment additive (B) was not used. Then, a pigment colorant for CF (Comparative Example 3) was obtained in the same manner as Example 25 described above, except that the composition obtained above was used instead of the pigment composition (3).

(Comparative example 4)
A composition containing PR177 not treated with a pigment additive was obtained in the same manner as Example 12 described above except that the pigment additive (B) was not used. Then, a pigment colorant for CF (Comparative Example 4) was obtained in the same manner as Example 26 described above except that the composition obtained above was used instead of the pigment composition (4).

(Comparative example 5)
A composition containing PR254 not treated with a pigment additive was obtained in the same manner as Example 13 described above except that the pigment additive (C) was not used. Then, a pigment colorant for CF (Comparative Example 5) was obtained in the same manner as Example 25 described above, except that the composition obtained above was used instead of the pigment composition (5).

(Comparative example 6)
A composition containing PR254 not treated with a pigment additive was obtained in the same manner as in Example 14 described above except that the pigment additive (C) was not used. Then, a pigment colorant for CF (Comparative Example 6) was obtained in the same manner as Example 26 described above except that the composition obtained above was used instead of the pigment composition (6).

(Comparative example 7)
A composition containing PY 138 not treated with a pigment additive was obtained in the same manner as Example 21 described above except that the pigment additive (G) was not used. Then, a pigment colorant for CF (Comparative Example 7) is obtained in the same manner as Example 25 described above, except that the composition containing PR138 obtained above is used instead of the pigment composition (13). The

(Comparative example 8)
A composition containing PY 138 not treated with a pigment additive was obtained in the same manner as Example 22 described above except that the pigment additive (G) was not used. Then, a pigment colorant for CF (Comparative Example 8) was obtained in the same manner as Example 26 described above except that the composition obtained above was used instead of the pigment composition (14).

<Evaluation>
Regarding each of the pigment colorants for CF of Examples 25 to 40 and Comparative Examples 1 to 8, (1) fluidity (storage stability), (2) gloss of a developed surface, (3) foreign matter in a coating, 4) Contrast and (5) luminance (Y value) were evaluated. Each evaluation method is shown below. The evaluation results are shown in Tables 2 and 3.

(1) Fluidity (storage stability)
Evaluation of fluidity by measuring the viscosity (mPa · s) of the pigment colorant for CF immediately after preparation (initial) and after standing for 1 month at 25 ° C. using an E-type viscometer. Set as a standard. The measurement conditions were temperature: room temperature (25 ° C.), and the number of revolutions of the rotor: 6 rpm. Moreover, while calculating "viscosity after standing / initial viscosity (%)", "storage stability" was evaluated according to the criteria shown below using the calculated value obtained.
:: “Viscosity after standing / initial viscosity” is 110% or less ×: “Viscosity after standing / initial viscosity” exceeds 110%

(2) A Gloss Bar Coater (Wing Wire Thickness 0.45 mm) was Used to Color-Finish a Pigment Colorant for CF on a polypropylene film to form a Glow surface. The gloss of the formed spread surface was observed visually and using a gloss meter, and the "gloss of the spread surface" was evaluated according to the criteria shown below. In addition, it can be determined that the higher the gloss of the developed color surface, the better.
:: very good ○: good ×: bad

(3) Foreign Matter in Coating Film A pigment colorant for CF was applied to a glass substrate using a spinner, dried at 90 ° C. for 2 minutes, and heated at 270 ° C. for 30 minutes to form a coating film. Using a microscope, the surface (coated surface) of the formed coating was observed at 200 × to confirm the presence or absence of foreign matter, and “foreign matter in the coating” was evaluated according to the criteria shown below.
:: no foreign substance ○: slightly foreign substance present ×: foreign substance present

(4) Contrast A pigment colorant for CF was applied to a glass substrate using a spinner, dried at 90 ° C. for 2 minutes, and heated at 230 ° C. for 30 minutes to form a coating. In addition, the speed of the spinner was changed to form three coated films. The bright brightness and dark brightness of the coating film formed using a contrast meter (manufactured by Eye System Co., Ltd.) were measured, and the contrast (bright brightness / dark brightness) was calculated. Furthermore, the coating film was subjected to color measurement using a spectrophotometer (trade name "U-2000A", manufactured by Hitachi, Ltd.) to measure the chromaticity x or y. An approximate straight line is drawn to the graph created by plotting the contrast against the chromaticity x or y, (i) in the case of PB 15: 6, the contrast of the chromaticity y = 0.120, (ii) of PR177 and PR254 In the case, the contrast of chromaticity x = 0.650 was read, and in the case of (iii) PY138, the contrast of chromaticity x = 0.426 was read. Then, the contrast ratio (%) of each example and comparative example was calculated with the contrast of comparative examples 1, 3, 5 and 7 as “100%”, and the “contrast” was evaluated according to the criteria shown below.
◎: 110% or more ○: 90% or more and less than 110% ×: less than 90%

(5) Brightness (Y value)
The pigment colorant for CF was applied to a glass substrate using a spinner and dried at 90 ° C. for 2 minutes to form a coating. In addition, the speed of the spinner was changed to form three coated films. The coatings were measured using a spectrophotometer to measure chromaticity x or y. An approximate straight line is drawn to the graph created by plotting the luminance (Y value) against the chromaticity x or y, and (i) in the case of PB 15: 6, the Y value of the chromaticity y = 0.120 ( ii) Y values of chromaticity x = 0.650 in the case of PR177 and PR254, and Y values of chromaticity x = 0.426 in the case of (iii) PY138, respectively. Moreover, it color-measured similarly and measured Y value about what heated each said coating film at 230 degreeC for 30 minutes. The difference (ΔY) between the Y value of the coating film treated at 230 ° C. and the Y value of the coating film treated at 90 ° C. was calculated, and the “brightness” was evaluated according to the criteria shown below.
○: ΔYY−0.1
×: ΔY <−0.1

  As shown in Tables 2 and 3, the pigment colorant for CF of the example has a lower viscosity, better storage stability, and a gloss on the display surface as compared to the pigment colorant for CF of the comparative example. It is understood that the film is good, no foreign matter is generated in the coating film, the contrast is high, and the luminance at 230 ° C. is hardly reduced as compared to the luminance at 90 ° C. From the above, it is clear that the pigment additives of the examples have excellent effects.

  Furthermore, the pigment compositions of the examples were used for printing inks such as offset inks; various paints such as nitrocellulose lacquers and melamine alkyd paints; and colorants of synthetic resins such as vinyl chloride resins. As a result, in each case, the pigment did not aggregate and showed good dispersibility. In addition, the pigment additives of the examples were used to prepare an electrophotographic dry or liquid toner, an ink for inkjet recording, an ink for thermal transfer recording, an ink for writing instruments, etc. which are particularly required to have high dispersibility recently. . As a result, excellent dispersibility was shown in each case.

  The pigment additive of the present invention is a printing ink (offset ink, gravure ink, etc.), various paints, plastics, pigment printing agents, dry or liquid toners for electrophotography, inks for inkjet recording, inks for thermal transfer recording, resists for color filters Is useful as an additive to be blended in an ink for writing instruments and the like, and its use is expected.

Claims (8)

The pigment additive which is a compound represented by following General formula (1) .

(In the general formula (1), D is a group represented by any of the following formulas (2) to (10), R is a single bond or a linear alkylene group having 1 to 4 carbon atoms And n represents a number from 1 to 4)

(In said Formula (2)-(10), * shows a coupling | bonding position with -NH in said General formula (1).
In the above formula (2), R ₁ represents a single bond, a methylene group or a divalent group represented by the following formula (I),
In formula (5), each R ₂ independently represents a hydrogen atom or a phenyl group,
R ₃ in the formula (5), R ₄ in the formula (6), and R ₅ in the formula (8) represent a methylene group or a divalent group represented by the following formula (I) ,
In said Formula (9), X shows a hydrogen atom or a halogen each independently)

A pigment composition comprising a pigment and the pigment additive according to claim 1 . The pigment composition according to claim 2 , wherein a blending amount of the pigment additive is 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment. Furthermore, a pigment derivative is contained as a pigment dispersant,
The pigment composition according to claim 2 or 3 , wherein the pigment derivative is at least one of a sulfonic acid pigment derivative and a sulfonamide pigment derivative. The compounding amount of the pigment derivative is 0.5 to 40 parts by mass with respect to 100 parts by mass of the pigment,
The pigment composition according to claim 4 , wherein a blending amount of the pigment derivative is 10 to 200 parts by mass with respect to 100 parts by mass of the pigment additive. A pigment colorant comprising the pigment composition according to any one of claims 2 to 5 and a film-forming material. The pigment colorant according to claim 6 , which is for image display, image recording, printing ink, writing ink, plastic, pigment printing, or paint. The pigment colorant according to claim 6 , which is for color filters.