TW201141957A - Pigment composition, and pigment dispersion using the same, ink-jet ink and electrophotographic toner - Google Patents

Abstract

The present invention provides a pigment composition containing a monoazo pigment and a monoazo pigment derivative having any one of the group represented by the formula (3) and the group represented by the formula (4). formula (3) -Y1-Y2-Y3 formula (4).

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pigment composition, a pigment dispersion using the pigment composition, an inkjet ink, and an electrophotographic toner. [Prior Art] Conventionally, yellow pigments for inkjet printing and electrophotographic use are mainly used such as CIPigment Yellow 12, CI Pigment Yellow 13, C. I· Pigment Ye 1 low 17, C. I· Pigment Ye 1 low 83 Disazo pigment, or such as CI Pigment Yel low 1, CI Pigment

Yellow 65, C. I. Pigment Yellow 74 monoazo pigment, or condensed azo pigment such as C. I. Pigment Yellow 93, C. I. Pigment Yellow 95, C. I. Pigment Yel low 128, and the like. In these orders, although the transparency and coloring power of the disazo pigment are good, there is a problem that the light resistance is low. Further, since dichlorobenzidine is used as a raw material, there is a concern about the safety of the decomposition product. Further, the condensed azo pigment is excellent in heat resistance and richness, but it is inferior to bis-chaotic pigment or monoazo pigment in terms of color strength, and has a problem of high price. On the other hand, a monoazo pigment is a pigment which is superior in terms of lightness or safety to a disazo pigment. Further, the monoazo pigment is superior in coloring power to the condensed azo pigment, and can be produced more inexpensively. In particular, C.I. Pigment Yellow 74 is excellent in hue and sharpness, and has been widely used in inkjet printing and electrophotography in recent years. In recent years, in the applications of inkjet printing, electrophotography, and the like, the quality level required for the printing of the object is improved, and it is required to uniformly disperse the fine pigment in the ink or the toner. However, in general, intense aggregation of pigment particles of fine pigments often results in poor dispersion stability. Therefore, if the dispersion is stored for a long period of time, defects such as an increase in viscosity or a precipitate may occur. Further, monoazo pigments are often poor in crystal stability to heat or solvent, and their tendency is particularly remarkable in fine monoazo pigments. Depending on the conditions of use, defects such as particle growth may occur once, and as a result, the coloring power or sharpness of the printed matter may be lowered. In order to improve the crystal stability of the above monoazo pigments, various studies have been conducted (for example, refer to Patent Documents 1 and 2). The following methods have been disclosed in Patent Documents 1 and 2: when synthesizing a monoazo pigment, an aromatic amine having a specific functional group is used as a diazo component, or an acetoacetanilide having a specific functional group is used. The compound is used as a coupler component and is coupled in a coexisting state, and a heterogeneous pigment is formed simultaneously with CI Pigment Yellow 74. In Patent Documents 1 and 2, a coloring composition for image recording is obtained by this method, and the heat resistance is improved regardless of the fine primary particle diameter, and the characteristics for inkjet and electrophotographic are imparted. However, the coloring composition obtained by this method has insufficient dispersion stability, and no fine single-coupled pigment having both heat and dispersion stability has been found. [Provisional Technical Documents] [Patent Document] 201141957 Patent Document 1: Japanese Laid-Open Patent Publication No. Hei No. Hei 10-158555. Patent Document 2: Japanese Patent Application Laid-Open No. 1-5--- Provided is a pigment composition comprising early azo (IV) which is excellent in heat resistance and dispersion stability, and a method for producing the same. Further, another object is to provide a pigment dispersion excellent in heat resistance and dispersion stability, an ink jet ink, a coloring tree product, and an electrophotographic toner. (Means for Solving the Problem) The present invention relates to a pigment composition containing a compound represented by the following formula (1) and a compound represented by the following formula (2);

Χβ

13 (wherein Χι to X5 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having a carbon number of 5 to 5, a carboxyl group, and a nitrate a sulfonic acid group, an amine sulfhydryl group, an amine fluorenyl group, a trifluorofluorene 323045 6 201141957 group, or a heterocyclic structure formed by combining adjacent groups; and X1 to X5 may have a substituent;

Xe to Χι. Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an ethylamino group, a carboxyl group, a sulfonic acid group, or a heterocyclic ring formed by combining adjacent groups. a structure; X6 to X1Q may also have a substituent;

Xn to Xi5 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an ethylamino group, a carboxyl group, a sulfonic acid group, and the following formula (3) a group shown by the formula or the following formula (4); Xu to χ15 may have a substituent; however, at least one of Xu to Xu is a group represented by the formula (3) and a formula (4) Any one of the formulas; (3) - YrY2 - 丫3 (wherein Υι denotes -S〇2NR' - or -CONR, -, ·, R, represents a hydrogen atom, and may have a substituent The alkyl group having a carbon number of 20 or less may have an alkenyl group having a carbon number of 20 or less or a aryl group having a carbon number of 2 Å or less which may have a substituent; Y2 represents a direct bond to which Υι and Y3 are bonded. a knot, an alkylene group having a carbon number of 20 or less having a substituent, an alkyl group having a carbon number of 2 Å or less having a substituent, an extended aryl group having a carbon number of 2 Å or less having a substituent, or "*Y2a-Y2b_Y2c-;

Yh and Yk each independently represent an alkylene group having a carbon number of 2 Å or less which may have a substituent, an extended alkenyl group having a carbon number of 2 Å or less which may have a substituent, or a carbon number which may have a substituent. The following aryl group; γη means that Y2a and 323045 7 201141957 only, R, 丫2 (: bond, direct bond of °, _〇_, ~C0-, -NR, -, or -s〇2_ The system is synonymous with the one defined by Υι; L represents -OR, -C00R], -NRA, -C0NRlR2, or 尺2; Here, Ri and R2 each independently represent a hydrogen atom and a carbon number which may have a substituent An alkyl group of 20 or less, an alkenyl group having a carbon number of a substituent or less, an aryl group having a carbon number of 20 or less having a substituent, or a heterocyclic structure formed by combining hydrazine with hydrazine; 1 and 匕 of R, Y2, and I each independently represent a heterocyclic structure formed by combining R' and % in ι, or a heterocyclic structure formed by combining 匕 with R or R2 in γ3); 4)

(wherein Y4 represents -NR, - or -0-; Y5 and Y6 each independently represent a group represented by the following formula (5), _〇R - nr'2, or a halogen atom; only 'Y4 , R in γ5, γ6, and (5) are synonymous with those defined by formula (3);

(wherein, Yz, Y3, and Y4 are synonymous with those defined by formulas (3) and (4)). Further, in the aspect of the embodiment of the pigment composition of the present invention, it can be listed in 323045 8 201141957, wherein the content of the compound represented by the formula (2) in the above pigment composition is the molar number of the compound represented by the formula (1). 01至40摩尔。 The total amount of moles of the compound of the formula (2) is 0.1 to 40% by mole. Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and the diazotide is a step of coupling the acetonitrile anilide compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetophenone anilide compound has the following formula (Ό Ό An anisidine compound and an acetophenone anilide compound represented by the following formula (8);

Formula (7)

NHCOCH2COCH3 type (8) 9 323045 201141957

• nhcoch2coch3 (wherein 1 to X1Q are synonymous with those defined by formula (1), and Xn to X15 are synonymous with those defined by formula (2)). Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and the diazotide is a step of coupling the acetaminophen compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetanilide compound contains an oxime represented by the following formula (7) An acetophenone compound and an acetophenone anilide compound represented by the following formula (8); and the method has the following steps: adding a formula to the aqueous diazotide solution of the aromatic amine represented by the formula (6) ( 8) a step of performing a coupling reaction to obtain a reaction mixture; and a step of reacting the reaction mixture with an acetophenone anilide compound represented by the formula (7);

10 323045 201141957 Equation (7)

Xl4 Xl5 X 13

NHCOCH2COCH3 X12

Equation (8) V V

NHCOCH2COCH3 (1: to X1Q is synonymous with the formula (1), and Xu to x15 is synonymous with the formula (2)). Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and the diazotide is a step of coupling the acetaminophen compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetanilide compound contains an oxime represented by the following formula (7) An acetanilide compound and an acetophenone anilide compound represented by the following formula (8); and the method has the following steps: adding a formula (6) at a predetermined flow rate in a buffer aqueous solution of pH 3 to 6 An aqueous solution of the diazotide of the aromatic amine shown, and an alkaline aqueous solution in which the acetophenone anilide compound represented by the formula (7) and the acetophenone anilide compound represented by the formula (8) are dissolved s 11 323045 Steps of 201141957, equation (6)

Nh2 x14

X12

NHCOCH2COCH3 type (8)

Xl4 Xl3

Xl2

NHCOCH2COCH3 X11 (wherein the X1Q system is synonymous with the formula (1), Xn to χ15 is synonymous with the formula (2)). Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and the diazotide is a step of coupling the acetophenone anilide compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetophenone anilide compound contains the following 12 323045 201141957 (7) And the method comprises the steps of: mixing the compound represented by the formula (2) with the diazotide of the aromatic amine represented by the formula (6) to obtain a mixture. a step of reacting the mixture with an acetophenone anilide compound represented by the formula (7);

Formula (7)

(乂之乂!至X!. is synonymous with the definition of (1)). Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and the diazotide is a step of coupling the acetaminophen compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetanilide compound contains an oxime represented by the following formula (7) An anilide compound; and the method comprises the steps of: mixing a compound 13 323045 201141957 represented by the formula (2) with an acetophenone anilide compound represented by the formula (7) to obtain a mixture; a step of reacting the mixture with a diazotide of an aromatic amine represented by the formula (6);

Formula (7)

(where X1 to Χίο are synonymous with those defined by equation (1)). Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and repeating the same a step of coupling the acetophenone anilide compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetophenone anilide compound contains the following formula (7) And the method comprises the steps of: adding the formula (6) to the aqueous buffer solution of pH 3 to 6 containing the compound represented by the formula (2) at the same time; An aqueous solution of an aromatic amine diazotide and an alkaline solution of an acetophenone compound represented by the formula (7) 14 323045 201141957;

NH 2

NHCOCH2COCH3 (wherein! to Xi. is synonymous with the definition of formula (1)). Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, which has a step of diazotizing an aromatic amine to obtain a diazotide, and the diazotide is a step of coupling the ethyl acetanilide compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetophenone compound contains ethyl acetonitrile represented by the following formula (7) An anisidine compound; and the method has the following steps: a slurry of a reaction product containing a diazotide of an aromatic amine represented by the formula (6) and an acetophenone compound represented by the formula (7) (slurry And a step of mixing with the compound represented by the formula (2); formula (6) 15 323045 201141957

X12 X" (wherein the formula is the same as defined in the formula (1).) Further, the present invention relates to a method for producing a pigment composition, which is a method for producing the above pigment composition, the method And the following steps: a step of wet-kneading a mixture containing the compound represented by the formula (1) and the compound represented by the formula (2) in the presence of a water-soluble inorganic salt and a water-soluble organic solvent; The step of removing the water-soluble inorganic salt and the water-soluble organic solvent in the mixture. Further, in the aspect of the pigment composition of the present invention, the compound represented by the formula (1) and the above pigment composition may be mentioned. The compound of the formula (2) has an average primary particle diameter of 200 nm or less. Further, in the embodiment of the pigment composition of the present invention, the pigment composition may be boiled by ion-exchanged water. The specific conductivity of the aqueous solution obtained by the extraction is less than 200 # S/cm. Further, in the aspect of the embodiment of the pigment composition of the present invention, the above pigment composition can be listed as 16 323045 201141957 In the case of the pigment composition of the present invention, the content of calcium, magnesium, and iron in the above pigment composition is exemplified. Further, the present invention relates to a pigment dispersion containing the above pigment composition and a liquid medium, and an ink jet ink containing the above pigment composition or the above pigment dispersion. The present invention relates to a colored resin composition containing the above pigment composition and a binder resin, and an electrophotographic toner containing the above pigment composition or the above colored resin composition. The subject matter contained in the patent application No. 2010-94563 filed on Apr. 16 is hereby incorporated by reference. The disclosure of the present invention is incorporated herein by reference. Inventive material composition 2: Disperse a mass of this pigment dispersion, inkjet ink, coloring resin group qualitative. ',,, like coloring _ has excellent resistance and dispersion [Embodiment] s slant cake The compound represented by the formula (1) of the present invention and the compound of 323045 17 201141957 represented by the formula (2) are explained. The halogen atom in the formula (1) and the formula (2) from ι to Xis can be enumerated: Said atom, gas atom, desert atom, helium atom. The alkyl group of the formula (1) and the formula (2) L to X! 5 having a carbon number of 1 to 5 may be exemplified by a mercapto group, an ethyl group, a propyl group or a different group. A propyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a second pentyl group, a neopentyl group, etc., but is not limited to such an example. And the alkoxy group having 1 to 5 carbon atoms in the range of 乂1 to 乂15 of the formula (2) may, for example, be a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a third butoxy group or a pentyloxy group. Base, neopentyloxy, and the like. However, it is not limited to these. The alkoxycarbonyl group having 1 to 5 carbon atoms in the formula (1) and the formula (2) in the range of 1 to 5 may be exemplified by an anthraceneoxycarbonyl group, an ethoxycarbonyl group, a third butoxycarbonyl group, a pentyloxycarbonyl group or the like. However, it is not limited to these. When the formula (1) and the formula (2) have the meanings 1 to 1 and Χδ to form a heterocyclic structure, the heterocyclic structure will be meaningful! To & && to L. The bonded benzene rings are combined to form a group having a heterocyclic structure (condensed ring group). The heterocyclic structure may also be a heterocyclic structure having a base or a thioketone group. The group having a heterocyclic structure may, for example, be an anthracene group, a benzimidazolone group, a benzofuranyl group, a benzononenyl group, a fluorenyl group, an iso-allinyl-dione group, or a dichlorinated group. 2-keto group and the like. However, it is not limited to these. One Χι to Xls may also have a substituent. Examples of the substituent include a halogen atom, an oxy group, an ethoxy group, an oxy-oxy group, an ethoxylated group, a phenyl group, a benzoquinone-based amine group and the like. However, it is not limited to these. The carbon number of the R', fluorene and R2 in the formula (3) which may have a substituent is 20 to 323,045. The alkyl group under 18 201141957 may, for example, be a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group or a hexyl group. Heptyl, octyl, decyl, decyl, dodecyl, octadecyl, isopropyl, isobutyl, isopentyl, second butyl, tert-butyl, second pentyl Base, third amyl, third octyl, neopentyl, cyclopropyl, cyclobutyl, cyclopentyl and the like. However, it is not limited to these. The alkenyl group having 20 or less carbon atoms which may have a substituent in R', fluorene and R2 of the formula (3) may, for example, be a vinyl group, a 1-propenyl group, an allyl group, a 2-butenyl group or a 3-butene group. Dilute, isopropyl, isobutyl, 1-pentyl, 2-indenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1-octenyl, 1 -octadecenyl, cyclopentenyl, cyclohexenyl, 1,3-butadienyl, cyclohexadienyl, cyclopentadienyl, difluoroethtoyl, 1-vinylidene, 2, 2 - 2> odoryl, 4-hydroxy-1-butenyl and the like. However, it is not limited to these. The aryl group having 20 or less carbon atoms which may have a substituent in R', fluorene and R2 of the formula (3) may, for example, be a phenyl group, a biphenyl group, a fluorenyl group, an anthracenylphenyl group, a xylyl group or a p-cyclohexyl group. Phenyl, p-cumenyl 1, p-cumenyl, and the like. However, it is not limited to these. Examples of the exudyl group having a carbon number of 20 or less in the Y2, Y2a, and Y2C of the formula (3) which may have a substituent include methylene, ethylene, trimethylene, and tetramethylene. Base, propyl, ethylmethylene, chloromethylene, dimercaptomethylene, bis(trifluoromethyl)methylene, and the like. However, it is not limited to these. Examples of the alkenyl group having a carbon number of 20 or less in the Y2, Y2a and Y2e of the formula (3) which may have a substituent include an ethylene group, a 1-methylvinyl group, a propenyl group, and a 1-butene group. Base, 2-butenyl group, :!-penpentenyl, 2-pentenene s 19 323045 201141957, and the like. However, it is not limited to these. The following formula ϋ=Υ2, Y2a and Y2c may also have a carbon number of 20/under which may be exemplified as: exophenyl, meta-phenyl, para-phenyl, -曱, -1' 2 - Stable base, 4' gas], 2_phenylene, 4-hydroxyl-I 2, benzene in 2 base -1,4' extended base, p, p-, biphenyl. However, when the heterocyclic structure is formed by ruthenium and osmium in the formula (3), the heterocyclic structure may be exemplified by a thiol group, a thiol group, or a heterocyclic structure. However, it is not limited to these. When RjR2 of R, γ2, and γ3 in Υ! forms a heterocyclic structure, the structure of f chen can be exemplified by: ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ ̄ However, it is not limited to these. The substituents of the substituents (R, n, Y2a, and Y2c) of the formula (3) and the formula (4) may be, in addition to the above-exemplified groups and the t substituents, Atom, methoxy, ethoxy, methoxycarboxy, ethoxycarbonyl, nitro, and the like. However, it is not limited to these. When the compound represented by the formula (2) has a group represented by the formula (3), L is preferably -S0-, - or -clear from the viewpoint of improving the heat resistance and dispersibility of the monoazo pigment. ―; [Preferred nucleobase, especially direct bond base [1 (CHL) nd; Y3 is better - service also. When the compound represented by the formula (2) has a group represented by the formula (4), it is preferably -NR'- from the viewpoint of improving heat resistance and dispersibility. " 4 . Further, in the compound represented by the formula (2), X1 is preferably an alkoxy group, particularly -0CH3 from the viewpoint of improving heat resistance and dispersibility; and & preferably 323045 20 201141957 % -N〇 2. The compound represented by the formula (2) is particularly preferably a compound having a group represented by the above formula (3) or a group represented by the formula (4), and preferably oxime and X3. Further, in the pigment composition of the present invention, it is preferred that the compound represented by the formula (1) and the compound represented by the formula (2) have the same base of \! to X5. The pigment composition of the present invention contains a compound represented by the formula (1) (hereinafter referred to as a monoazo pigment) and a compound represented by the formula (2) (hereinafter referred to as a monoazo pigment derivative). The compound represented by the formula (2) has an effect of improving the dispersibility of the compound represented by the formula (1) and further suppressing the growth of crystal. Therefore, a fine pigment composition excellent in heat resistance and dispersibility can be obtained as compared with the compound represented by the formula (1) alone. Further, since the compound represented by the formula (2) has the same effects in various methods of use, a pigment composition excellent in heat resistance and dispersion stability can be produced by various methods. The monoazo pigment used in the present invention is not particularly limited, and examples thereof include CI Pigment Yellow 1, CI Pigment Yellow 2, CI Pigment Yellow 3 'CI Pigment Yellow 4, CI Pigment Yellow 5 > CI Pigment Yellow 6, CI Pigment Yellow 9 > CI Pigment Yellow 49, CI Pigment Yellow 61 'CI Pigment Yellow 62 > CI Pigment Yellow 65 ' CI Pigment Yellow 73 ' CI Pigment Yellow 74, CI Pigment Yellow 75 > CI Pigment Yellow 97 ' CI Pigment Yellow 98 ' 21 323045 201141957 CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment

Yellow 105 , Yellow 116 , Yellow 130 , Yellow 151 ' Yellow 167 , Yellow 169 , Yellow 181 , Yellow 203 , Orange 1 , Orange 60 , C, I. Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment CI Pigment

Yellow 111 , Yellow 120 , Yellow 133 , Yellow 154 , Yellow 168 , Yellow 175 , Yellow 194 , Yellow 213 , Orange 36 , Orange 62 , C. I. Pigment Orange 64 , etc. Among them, C. I. Pigment Ye 1 low 74 is particularly preferable in terms of hue or vividness and transparency. These single azo pigments may be used singly or in combination of plural kinds. The form of the monoazo pigment used in the present invention is not particularly limited. Commercially available pigments can be used directly or in combination. Further, if necessary, it may be micronized into desired particles by an acid pasting method, a solvent salt polishing method, or a dry milUng method. Used again. The monoazo pigment of the present invention represented by the method of synthesis can be represented by the following public synthesis method, and the first example can be exemplified by adding the diazotide of the aromatic amine to the test of the anilide compound. = acetamidine aniline compound is dissolved in the pH of 1 〇 不 不 甘 甘, i: λ z; 上 Ί Ί 水 Ί Ί 洛 洛 Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί Ί : 323045 22 201141957 to 6 suspension (slurry). On the other hand, the aromatic amine represented by the formula (6) is added to an aqueous hydrochloric acid solution to prepare a suspension having a pH of 2 or less, and then cooled to 5 ° C or lower, and then sodium nitrite is added to make the formula (6) The aromatic amine shown is diazotized. After the end of the diazotization, an amine was continuously acid-added to the obtained reaction mixture to remove the excess methylene acid, and an aqueous solution of the heavy gas was prepared. Next, the above-prepared aqueous solution of diazotide is added to a slurry of 10 to 50 ° C of an acetophenone anilide compound for 30 to 90 minutes, thereby performing a coupling reaction, and then the resulting slurry is filtered, washed with water, and dried. And pulverization, and a monoazo pigment can be obtained. In the second example, a method of adding an aqueous alkaline solution of an acetanilide compound to an aqueous solution of an aromatic amine in a diazotide is exemplified. First, the ethyl acetophenone compound represented by the formula (7) is dissolved in an alkaline aqueous solution having a pH of 10 or more to prepare an aqueous solution. On the other hand, the aromatic amine represented by the formula (6) is added to an aqueous hydrochloric acid solution to prepare a suspension having a pH of 2 or less, and then cooled to 5 Torr or less, and then sodium nitrite is added to give the formula (6). The aromatics are free of amines for diazotization. After the completion of the diazotization, the obtained reaction mixture = added amine sulfonic acid to remove excess nitrous acid, and then an aqueous solution containing acetic acid and hydrogen fluoride was added, and an aqueous solution of diazotide having a enthalpy of 2 to 4 was prepared. The aqueous solution of the above-obtained acetophenone anilide compound is added to the heavy gasification aqueous solution of hydrazine to 30 ° C for 1 to 77 hours, thereby undergoing a two-coupling reaction, and then the resulting slurry is shouted and washed. , dry, and smashed to obtain a monoazo pigment. For example, an aqueous solution of an aromatic amine diazotide and an aqueous test solution of a acetamidine compound can be added to a predetermined flow rate (for example, a flow rate of 323045 23 201141957) to a previously added acetic acid and hydrogen. A method of preparing an aqueous solution by using a base such as sodium oxide. First, the acetophenone anilide compound represented by the formula (7) is dissolved in an alkaline aqueous solution having a pH of 10 or more to prepare an aqueous solution. On the other hand, the aromatic amine represented by the formula (6) is added to an aqueous hydrochloric acid solution to prepare a suspension having a pH of 2 or less, and then cooled to 5 ° C or lower, and then sodium nitrite is added to make the formula (6) The aromatic amine shown is diazotized. After the end of the diazonization, the amine sulfonic acid was added to the obtained reaction mixture t to remove excess nitrous acid to prepare an aqueous solution of diazotide. Further, a buffer solution in which pH 3 to 6 of acetic acid and sodium hydroxide are dissolved is prepared in the reaction tank. Next, the aqueous solution of the diazotide prepared above and the aqueous solution of the acetanilide compound are simultaneously added to the buffer prepared in the reaction tank for 30 to 90 minutes, and the liquid temperature of the buffer is ensured to be 10 to 50°. C, pH is 6 or less, whereby a coupling reaction is carried out, and then the resulting slurry is filtered, washed with water, dried, and pulverized to obtain a monoazo pigment. The aqueous solution to be tested in the above examples is not particularly limited, and an aqueous solution of sodium hydroxide, a potassium hydroxide aqueous solution, a hydroxide aqueous solution, an aqueous sodium sulfate solution or the like can be used. The buffer (buffer aqueous solution) is not particularly limited, and an acetate buffer, an acid buffer, a citric acid buffer or the like can be used. Further, in the diazotide aqueous solution, the concentration of the diazotide may be, for example, 0.01 to 1.0 mol/L; in the slurry of the acetamidine compound, the concentration of the acetophenone compound may be set to, for example, 0.01 to 1.0. 5摩尔/L。 The molar concentration of the acetonitrile anilide compound, the concentration of the acetophenone anilide compound may be, for example, 0.02 to 1. 5mol / L. The aromatic amine used in the present invention may, for example, be 2-aminobenzoic acid, 24 323045 201141957 3-aminobenzoic acid, 4-aminobenzoic acid, 2-(trifluoromethyl)aniline, 3-(trifluoro Methyl)aniline '4-(trifluoromethyl)aniline, o-anisidine, m-methoxyaniline, p-methoxyaniline, 2-nitroaniline, 3-nitroaniline, 4-nitrostamine, 2-methoxy-4-nitroaniline, 2-methoxy-5-nitroaniline, 4-methoxy-2-nitroaniline, 2-methyl-3-nitroaniline, 2-methyl-4_ nitrate Aniline, 2-mercapto-5-nitroaniline, 2-methyl-6-nitroaniline, 3-methyl-4-nitroaniline, 4-methyl-2-nitroaniline, 4-methyl-3-nitrate Strepamine, 5-methyl-2-nitroaniline, 2-chloro-4-nitroaniline, 2-chloro-5-nitroaniline, 4-chloro-2-nitroaniline, 4-gas-3-nitroaniline, 5-chloro-2-nitrolamine, 2-amino-5-nitrobenzenesulfonic acid, 4-amino-2-nitrobenzenesulfonic acid, 4-amino-3-nitrobenzenesulfonic acid, 2 -Chloro-4-toluidine, 2-chloro-5-toluidine, 2-chloro-6-toluidine, 3-chloro-2-toluidine, 3-chloro-4-nonanilide-, 4-chloro-2 -toluidine, 4-chloro-3-toluidine, 5-chloro-2-indanylamine, 3-amino-4-chlorobenzamide, 4-amino-3-chlorobenzamide, 4-Amino-3-methoxy-N-phenylbenzenesulfonamide, 4-amino-N-(4-aminoformamidophenyl)benzamide, Aminoterephthalic acid II Methyl ester, 5-aminoisophthalic acid dinonyl ester, 6-amino-7-chloro-4-methylquinoline-2(1H)-one, 5-aminoisoindoline-1,3 - Diketone and the like. These may be used singly or in combination of plural kinds. The acetophenone anilide compound used in the present invention may, for example, be acetanilide, o-acetoacetanisidide, acetamidine, 2'-chloroacetate Aniline, 4'-chloroacetic acid aniline, N-acetamido-o-toluidine, N-acetamido-p-toluidine, o-acetamidine, and acetamidine Oxyaniline, acetoacetic acid p-ethoxyaniline, 4,-acetamidoethyl 323045 201141957 acetanilide, 2',4'-dimethylethionanilide, 4'-chloro-2' - Methyl styrene, aniline, 5'-chloro-2'-methoxy ethoxylated aniline, 4'-chloro-2',5-dimethoxy oxyacetamidine, 5-acetonitrile Aniline-2-benzimidazolidinone, N-(7-decyloxy-2,3-di-oxy-1,2,3,4-tetrahydroquinoxalin-6-yl)-3- Side oxybutylamine and the like. These may be used singly or in combination of plural kinds. When the pigment is refined by the acid gelatinization method, the monoazo pigment is dissolved in concentrated sulfuric acid, and then mixed with a large amount of excess water, whereby fine pigment particles are precipitated. Subsequently, the mixture is repeatedly filtered, washed with water, and then dried to obtain finely divided pigment particles. The method of the acid gelatinization method is not particularly limited, and examples thereof include a method in which a monoazo pigment is dissolved in 5 to 30 times by weight of 98% monosulfuric acid, and the obtained sulfuric acid solution is further 5 to 30 times by weight thereof. The water is mixed. In this case, the degree of dissolution of the monoazo pigment in the sulfuric acid is not particularly limited as long as it does not cause a reaction such as decomposition of the raw material or sulfonation, and can be carried out, for example, in the range of 3 to 40 °C. Further, the method of mixing the sulfuric acid solution of the monoazo pigment with water or the temperature is not particularly limited, but in many cases, the particles tend to precipitate at a higher temperature at a lower temperature, and a finer tendency is precipitated, so it is preferably at 0°. It is carried out in the range of C to 60 °C. The water to be used at this time may be any industrially usable such as tap water, well water or warm water, and in order to reduce the temperature rise during precipitation, it is preferred to use pre-cooled water. The method of mixing the sulfuric acid solution with water is not particularly limited, and any single azo pigment can be mixed by any method as long as it can be completely precipitated. For example, it may be deposited by injecting a sulfuric acid solution into pre-prepared ice water or by continuously injecting water or the like using a device such as suction 26 323045 201141957 (aspirator). The slurry obtained by the above method is filtered and washed to remove the acidic component, and then dried and pulverized, whereby a micronized monoazo pigment can be obtained. When the slurry is filtered, the slurry in which the sulfuric acid solution and water are mixed may be directly filtered. When the slurry has poor filterability, it may be heated and stirred before filtration to be filtered. In addition, it is also possible to neutralize the slurry with various bases and then carry out the hydrazine. When the pigment is refined by a solvent salt polishing method, a mixture of at least three components of a monoazo pigment, a water-soluble inorganic salt, and a water-soluble solvent is formed into a clay shape, and then kneaded by a kneader or the like. . Next, the kneaded mixture was poured into water, and stirred in various mixers to form a slurry. It is filtered to remove water-soluble inorganic salts and water-soluble solvents. The above-mentioned slurry liquefaction, filtration, and water washing are repeatedly carried out to obtain a finely divided monoazo pigment. As the water-soluble inorganic salt, sodium chloride, sodium sulfate, potassium chloride or the like can be used. These inorganic salts can be used in an amount of 1 part by weight or more, preferably 20 times or less by weight of the monoazo pigment. When the amount of the inorganic salt is less than 1 part by weight, it is difficult to sufficiently fine the pigment. On the other hand, when it is more than 20 times by weight, a large amount of labor is required to remove the water-soluble inorganic salt and the water-soluble solvent after the kneading, and at the same time, the amount of the pigment which can be treated at one time becomes small, so that from the viewpoint of productivity The words are not good. In the method for miniaturizing the above-mentioned pigment, heat is often generated by kneading. Therefore, from the viewpoint of safety, a water-soluble solvent having a boiling point of about 120 to 250 ° C is preferably used. Examples thereof include 2-(methoxymethoxy)ethanol, s 27 323045 201141957 2 dioxyethanol, isopentyloxy)ethanol, 2-(hexyloxy)ethanol, ethanol *diethyl-alcohol, - ethylene glycol monoterpene ether, diethylene glycol monoethyl sulphate, diethanol monobutyl (tetra) diethylene glycol, triethylene glycol monomethyl phthalate, alcohol, dioxime I propanol, ethoxylated alcohol such as alcohol ,: two two propanone yeast early mystery, dipropylene glycol single-hex scale, low molecular weight polypropylene glycol. When the pigment is refined by a dry grinding method, the monoazo pigment is dry-pulverized by various pulverizers to be finely pulverized. In this method, the pulverization is performed by collision and friction of the pulverization medium with each other. The apparatus used for the dry grinding method is not particularly limited, and examples thereof include a ball mill in which a dry pulverizing device containing a pulverizing medium such as beads (5) 1 mi (1) or an attritor, a vibrating mill Wait. When dry pulverization is carried out using this apparatus, the inside of the pulverization container may be decompressed as needed, or an inert gas such as nitrogen may be filled. Further, after the completion of the dry polishing method, the solvent salt polishing method or the solvent treatment may be carried out. The above-mentioned method for refining the pigment may be used singly or in combination of a plurality of azo pigments. Further, it may be used after being dried, pulverized, and powdered, or may be used in the form of a water-containing cake (_) before drying. Examples of the monoazo pigment derivative used in the present invention include compounds of the structures shown below. However, the invention is not limited to the examples. These monoazo pigment derivatives may be used singly or in combination of plural kinds. If necessary, it can be refined into the desired particle size by the method of the uni-nitrogen pigment (4). The monovalent pigment derivative of the present invention can be synthesized by a known method, for example, in the same manner as the above-mentioned monoazo pigment synthesis 323045 28 201141957. In this case, the acetophenone compound may be a compound obtained by introducing a group represented by the formula (3) or a group represented by the formula (4). The acetaminophen compound may be used singly or in combination of plural kinds.

S 29 323045 201141957 o2n οα Valley

Och3 coch3 N=N—CHCONH conh(ch2)3n(c2h5)2 o2n

OCH3 NH(CH2)3N(C2H5)2 c〇ch3 h N={ N=N-CHC〇NH-^ N—^ N XNH(CH2)3N(C2H5)2 och3 o2n

O2n

(pOCHa N=N-CHCONH 〇CH3 COCH3 N=N-CHCONH

So2nh 〇ch3 S02NH(CH2>3N(CH3>2 〇2n

OCH3

O2n

COCH3 N=N—CHCONH—^ OCH3 COCH3 N=N—CHCONH-

So2nh(ch2)3n(ch3)2 CONH(CH2)3N(C2H5)2 NH(CH2)3N(C2H5)2 PCH3 o2n

COCH3 ^N-CHCONH

H )^\ νΛ-<ν

N〇2 f COCH3 / ^—N=N—CHCONH—^

NH(CH2)3N(C2H5)2 N(C2H5)2 N(C2H5)2

NO

2 HN COCH3 N-N-diHCONH—^

NH(CH2)2N p

OH

OCH3 CeH5HN02S

COCH3 N=N-CHCONH SQ2NH so2nh2 30 323045 201141957

Nh2

Conh2

s 31 323045 201141957

Cl

NO

2

COCH3 N-N-CHCONH

O-

Cl

N05

COCH3 N=N—CHCONH

So2nh CONH(CH2>3N(C2H5)2 NH(CH2)3NH OCH3

Cl

N02

COCH3 N=N-CHCONH

NO, Cl

COCH3 N=N—CHCONH H /N==\-ν>ΝΛ-<Ν och3

NH(CH2)2N

Cl

COCH3 N=N-CHCONH so2nh(ch2)3n(ch3)2 och3

COCH3 N=N—CHCONH NHC2H5 nhc2h5 och3

COCH3 N=N—CHCONH-

S02NH

OCH3 CF,

COCH3 N-N-CHCONH-

COCH3 N=N—CHCONH

Ό~ΗίΝ OH S02NH(CH2)3N(C4H9)2 NH(CH2)3N(C4H9)2 32 323045 201141957

So2nh OCH3

H3cooc CONH(CH2)3N(C2H5)2 h3cooc

POOCH3 COCH3 N=N-CHCONH I o so2nh COOCH3 h2noc -O'

HNOC

s 33 323045 201141957 CH, Cl

COCH3 N=N—CHCONH

CONH(CH2)3N P2H5

Cl

Ch3Γ/n=n_ o 〒〇CH3 /==\ h yN=( -CHCONH—^》—N—^ N 〇

N〇2 H3CO

COCH3 N=N—CHCONH-

N=<m! C2H5 ,nh(ch2)3n(c4h9)2

NO H3CO

COCH3 N=N-CHCONH- 2

OH nh(ch2>2n(ch3)2 mn nh(ch2)2n(ch3>2 o H. o

?〇ch3

:N a CHCONH

CONHN N—CH3

〇 H

COCH3 N=N-CHCONH CONH(CH2)3N(C2H5)2

Cl

COCH3 N=N-CHCONH

COCH3 n=n-chconh CONH(CH2>3N(CH3)2 34 323045 201141957 In the present invention, when the pigment composition is prepared, the monoazo pigment and the monoazo pigment derivative can be mixed by any method. For example, a method in which a previously synthesized monoazo pigment and a monoazo pigment derivative are directly mixed in a powder form, or a method in which individual aqueous slurries are mixed with each other; a method for adding a powdery or dissolved monoazo pigment derivative to a water slurry of a pigment; a method for simultaneously producing a monoazo pigment derivative when synthesizing a monoazo pigment; and synthesizing a single sheet in the presence of a monoazo pigment derivative A method of azo pigment; a method of kneading a pigment composition composed of a monoazo pigment and a monoazo pigment derivative by a solvent salt polishing method, etc. Dispersibility and crystal stability can be obtained by any of these methods The pigment composition of the present invention has a content of the monoazo pigment derivative in the total amount of the monoazo pigment and the monoazo pigment derivative, preferably 0.1 mol. % 。 。 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫 莫When the amount of the ear is 0%, the dispersion stability and crystal stability of the obtained pigment composition tend to be insufficient. On the other hand, when it exceeds 40 mol%, significant dispersion stabilization accompanying the increase in the amount of addition cannot be obtained. The effect or crystal stabilization effect, and the coloring power tends to decrease due to the decrease in the content of the monoazo pigment. The method for producing the pigment composition of the present invention, in the above-exemplified method, is particularly preferred: synthesis a method of simultaneously producing a monoazo pigment derivative in a monoazo pigment; or a method of synthesizing a monoazo pigment in the presence of a monoazo pigment derivative; or a monoazo pigment and a monoazo pigment derivative 35 323045 201141957 The pigment composition of the composition is subjected to the solvent salt grinding method. When these methods are used to produce a pigment composition, the monoazo pigment and the single method are very fine, and a uniformly mixed pigment-grade nitrogen is obtained. Pigments are used in various In the meantime, dispersibility and crystal stability are obtained. Therefore, a pigment composition having high force or transparency is particularly preferable. A coloring method is also used to produce a pigment composition by using a synthetic monoazo pigment. In the case of the product, the aniline compound derived from the bismuth pigment of the formula (7) and the acetophenone of the formula (8) can be abbreviated to be a compound of the formula B, and In the above example, the pigment composition is produced in the same manner as the method of blending the pigment. The amount of the acetophenone compound which synthesizes the mono-oxime is preferably the compound of the formula (8) and the formula (8) The amount of oxime shown by acetonitrile B is in the range of 0.1% to 40% by mole. The total amount of the amine compound is 30% by mole, and particularly preferably 0.5% by mole to 2〇莫C3摩尔% 〇. 1 mole%, the dispersion of the pigment composition to be served has a tendency to be insufficient for Xia Weida. On the other hand, when the = raw, crystal stability method obtains a significant fraction, ear associated with an increase in the amount of addition. In the series, there will be no crystal stabilization effect, and the tendency of the fruit or the knot to decrease due to the content of the monoazo pigment is lowered. When the pigment composition is produced by a method of using a single azo-magic substance in the presence of a monoazo-magic substance, the sigma azo pigment derivative can be added to the base component (the diazo 5 is good) The azo anthraquinone aniline compound) or the pH 3 6 horse-forming agent component (Ethylene B.) 323045 36 201141957 Formula for producing a pigment composition. The method for producing the pigment composition of the present invention specifically includes the following methods. The method for producing a pigment composition is a step of diazotizing an aromatic amine to obtain a diazotide, and coupling the diazotide with an acetophenone aniline compound, wherein: A. aromatic The amine contains an aromatic amine represented by the formula (6), and the ethyl acetanilide compound contains an acetophenone anilide compound represented by the formula (7) and an acetophenone anilide compound represented by the formula (8); The aromatic amine contains an aromatic amine represented by the formula (6), and the acetanilide compound contains an acetophenone anilide compound represented by the formula (7) and an acetophenone anilide compound represented by the formula (8). ; and has the following steps: (6) a step of adding a acetophenone anilide compound represented by the formula (8) to the aqueous solution of the aromatic amine of the aromatic amine to carry out a coupling reaction to obtain a reaction mixture; and the above reaction mixture is represented by the formula (7) a step of reacting the acetaminophen compound; C. The aromatic amine contains an aromatic amine represented by the formula (6), and the acetanilide compound contains an acetophenone compound represented by the formula (7) and An acetaminophen compound represented by the formula (8); and having the following steps: adding the weight of the aromatic amine represented by the formula (6) at a predetermined flow rate in an aqueous buffer solution of pH 3 to 6 a step of dissolving an aqueous solution of a nitride and an alkaline aqueous solution in which an acetophenone anilide compound represented by the formula (7) and an acetophenone anilide compound represented by the formula (8) are dissolved; D. an aromatic amine containing a formula (6) The aromatic amine shown, acetamethylene benzene s 37 323045 201141957 The amine compound contains an acetophenone anilide compound represented by the formula (7); and has the following steps: a monoazo pigment derivative and a formula ( 6) The azide of the aromatic amine shown is mixed a step of obtaining a mixture; a step of reacting the above mixture with an acetamidine compound represented by the formula (7); E. an aromatic amine containing an aromatic amine represented by the formula (6), acetamidine The aniline compound contains an acetophenone anilide compound represented by the formula (7); and has a step of mixing a monoazo pigment derivative with an acetophenone anilide compound represented by the formula (7) to obtain a mixture. a step of reacting the above mixture with a heavy IL compound of an aromatic amine represented by the formula (6); F. an aromatic amine containing an aromatic amine represented by the following formula (6), an acetanilide compound The ethyl acetophenone compound represented by the formula (7) is contained; and the following steps are carried out: in the aqueous buffer solution containing pH 3 to 6 of the monoazo pigment derivative, the formula (6) is simultaneously added at a predetermined flow rate. a step of forming an aqueous solution of an aromatic amine diazotide and an alkaline solution of an acetophenone compound represented by the formula (7); G. an aromatic amine containing an aromatic amine represented by the formula (6), Acetyl anilide compound contains formula (7) An acetanilide compound; and a slurry of a reaction product containing a diazotide of an aromatic amine represented by the formula (6) and an ethyl acetophenone compound represented by the formula (7); a step of mixing with a monoazo pigment derivative; 具有 having a mixture containing a monoazo pigment and a monoazo pigment derivative in the presence of a water-soluble inorganic salt and a water-soluble organic solvent. 38 323045 201141957 The step of mixing, and then the step of the water-soluble organic solvent and the water-soluble organic solvent from the above mixture. ...the machine of the orphan buffer aqueous solution, the alkaline aqueous solution, the water-soluble no, the organic solvent, etc. or the diazotized water, the liquid container, the water, each of the ten to the night, the test of the amine compound The concentration of the solution or the like, or the time required for the addition, the method of producing the pigment, or conventionally known; gas: depending on the method of manufacture. The pigment composition obtained by the present invention can also be produced by a combination of the above-mentioned hydrazine, and the above. Further, the pigment composition of the above may be micronized by a grinding method or a grinding-reducing material as needed, and the particle size may be reused. The method at this time can be carried out in the same manner as in the case of the above monoazo pigment. Further, the pigment composition of the present invention can be produced by adding a resin or an active agent or the like in any of the above-mentioned methods. These additives are used in any stage of the pigment composition. For example, it can be used together with an aromatic amine or an aniline aniline compound in the stage of synthesizing a pigment composition, or a resin used at the time of performing a crystallization method, a solvent-based grinding method, a dry milling method, or the like. The type is not particularly limited, and examples thereof include rosin resin, propylene glycol resin, and styrene _: resin, polyester resin, polyamine resin, and polyurethane. A resin, a fluorine resin, a vinyl naphthalene-acrylic resin, a styrene-maleic acid resin, or the like. These resins may be used alone or in combination of plural kinds. Further, the resins may be from 0 to 30 weights relative to the pigment group 323045 39 201141957. /Q is preferably used in the range of 1 to 15% by weight. The type of the surfactant is not particularly limited, and examples thereof include a fat sulfonium salt, a calcined sulphuric acid g salt, an alkyl aryl sulfonate, a decyl naphthylate, a dialkyl sulfonate, and a dioxane. Sulfonic acid succinate, alkyl diaryl ether dihectorate, alkyl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl Ether sulfate, naphthalenesulfonic acid morpholine condensate 'polyoxyethylidene alkyl phosphate ester salt, glyceryl borate fatty acid ester, polyoxyethylene ethyl glyceride fatty acid temple, polyoxyethylene ethyl ether, polyoxygen Ethyl alkyl aryl ether, polyoxyethylene ethyl propyl block polymer, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid vinegar, polyoxyethylene sorbitol Fatty acid ester, glycerin fatty acid ester, polyoxyalkylene amine amine, fluoroquinone nonionic surfactant, polyoxic (si 1 i ) nonionic surfactant, alkylamine salt, four Amine salt, alkyl pyridinium salt, alkyl imidazolium salt, and the like. These surfactants may be used alone or in combination of plural kinds. Further, the surfactants may be used in an amount of from 0.3 to 20% by weight, preferably from i to 10%, based on the pigment composition. The pigment composition of the present invention preferably has an average primary particle diameter of 200 nm or less, more preferably 150 nm or less, of the pigment contained in the composition (mixture of monoazo pigment and monoazo pigment derivative). It is below i〇〇nm. When the average primary particle diameter exceeds 200 nm, the coloring power may be poor when used for various purposes. "In addition, a precipitate may be generated in the dispersion or the ink during storage. 40 323045 201141957 In the present invention, the electron microscopy or penetrating electrons of the pigment composition can be measured using a scanning electron microscope or a transmission electron microscope. For example, the sweeping type of electricity pair constitutes each of the aggregates; = the photograph of the particle of the member's needle, the largest part of the diameter of each of the sub-fields contained in the same field of view. - the average particle, the average value of the obtained value, the extract of the product, the pigment composition by ion-exchanged boiled === the specific conductivity of the liquid, in the pigment composition Three people were included as indicators in the contents. In general, the ionic impurities of the pigment composition are known to be scattered in the case of various materials. In the present invention, the specific conductivity of the aqueous solution obtained by extracting the pigment composition by the parent and the boiled water is preferably less than 200/zS/cm, more preferably less than 15 Ms/cm, and particularly preferably not up to s/ Cm. The measurement of the content of the ionic impurities can be carried out in accordance with the method described in the examples. The method for reducing the ionic impurities contained in the pigment composition is not particularly limited as long as the specific conductivity of the aqueous solution obtained by subjecting the pigment composition to the ion-exchanged water-cooking material is in the above-described range, and for example, The method of filtering and washing the pigment composition after repeated preparation. The type of water to be used at this time is not particularly limited, and it is preferably one which does not contain ionic impurities such as distilled water or ion-exchanged water.

Further, in the pigment composition of the present invention, the total content of calcium, magnesium, and iron is preferably less than 300 ppm, more preferably less than 2 ppm, and particularly preferably less than 150 ppm. Further, the content of each of the above metal elements is preferably less than 323,045, 41, 2011, 41,957, 150 ppm, respectively, more preferably less than 10 ppm, and particularly preferably less than 80 ppm. If the total content of calcium, magnesium, and iron is 300 ppm or more, or the content of individual metal elements is 150 ppm or more, when the pigment composition is used for inkjet printing, there is an ink flow in the printer. The nozzle portion of the track or the print head generates insoluble matter 'because it becomes a cause of nozzle clogging. Various methods are known for measuring the contents of calcium, magnesium, and iron. For example, I cite the following methods: adding nitric acid to the pigment composition and decomposing it by microwave, and then diluting the resulting solution to an appropriate concentration. The measurement of the measured content by inductively coupled plasma luminescence analysis ((10)) can be carried out in accordance with the method described in the examples. For reducing the content of calcium, magnesium, and iron contained in the pigment composition, for example, the pigment composition is prepared by slurrying in a solution after preparation, and then repeatedly filtering and The type of the acid to be used in the case of washing is not particularly limited, and examples thereof include sulfuric acid, @夂, and 酴 酴 ❶ ❶, and the type of water used for washing is not particularly limited. Exchange water and other ionic impurities. The pigment dispersion system containing the pigment composition of the present invention and the liquid composition 2 comprises: a pigment phase-reduction dispersion in which the pigment of the present invention is dispersed in an aqueous medium, and the present invention is dispersed in an organic solvent. Any of the 1C oily pigment dispersions. The aqueous pigment dispersion of the present invention can be prepared by dispersing the pigment composition of the present invention, a mixture of various resins to be dispersed, a surfactant, and the like, and adding the above-mentioned raw materials. In addition, various additives may be added to redispersion as needed. When the pigment dispersion is prepared 323045 42 201141957 The order of addition of the raw materials of the present invention is not particularly limited. It is particularly limited, and the content of the pigment group is not used in the range of 5 to 10 in the desired pigment dispersion, and particularly preferably 10 to 40% by weight. The content of the aqueous medium to be used in the production of the pigment dispersion is not particularly limited, and it is preferred that (4) the exchanged water such as metal ions or the like is removed. The water-based medium is preferably 30 to 95% by weight in the water. In addition, water can be mixed with a water-soluble solvent as needed to be used as a water source medium. The water-soluble solvent is not particularly limited, and examples thereof include ethyl alcohol, diethylene glycol, propylene glycol, triethylene glycol, polyethylene glycol, glycerin, monoethylene glycol, dipropylene glycol, and decyl alcohol; and ethylene glycol; Monobutyl ether, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, 1> 2-hexanediol, N_methyl-2-pyrrolobutyrrolidone, 2, 4, 6-hexanetriol, four Furan methanol, 4-methoxymethylpentanone, and the like. These may be used alone or in combination. When the water-soluble solvent is used, the content of the water-soluble solvent is preferably from 1 to 50% by weight in the aqueous pigment dispersion. 7. The resin used in the production of the aqueous pigment dispersion is not particularly limited as long as it can disperse the pigment composition in an aqueous medium. For example, a resin which can be used in the production of a pigment composition can be used. These resins can be used alone. Two kinds can also be used in combination. Further, the amount of use is not particularly limited, and is preferably from 5 to 30% by weight, more preferably from 1 to 20% by weight, based on 5% by weight of the aqueous pigment dispersion. Further, the interfacial activity used in the production of the aqueous pigment dispersion is 323045 43 201141957. The "dispersible pigment composition in the water n" is not particularly limited, and for example, an interface which is not usable when the pigment composition is produced can be used. The active agent may be used alone or in combination of (4) plural kinds. Further, the amount of use is not particularly limited, and is preferably from 0.5 to 30% by weight in the aqueous pigment dispersion. It is preferably from i to 2% by weight. In addition, when making an aqueous pigment dispersion, additives such as a retarder, a pH adjuster, and an antifoaming agent may be used as needed. The mold inhibitor is used to prevent the dispersion of the aqueous pigment. The type of the anti-fungal agent is not particularly limited, and examples thereof include sodium dehydroacetate, sodium alginate, sodium 1-oxo-thiopyridine, and 1-oxo-sulfur. An alcoholic zinc pyridine, an anthracene, a 2-benzisothiazoline-3-one, an amine salt of a benzisothiazolin-3-one, etc. These are preferably 0.05 to 2% by weight in the aqueous pigment dispersion. Used within the range. pH adjuster is used to make the pH of the aqueous pigment dispersion The type of the pH adjuster is not particularly limited, and examples thereof include various amines, various inorganic tests, ammonia, various buffer solutions, etc. Antifoaming agents are used to prevent bubbles in the production of aqueous pigment dispersions. The type of the antifoaming agent is not particularly limited, and any one of commercially available ones can be used. For example, SURFYNOL 104A, SURFYNOL 104E, SURFYN0L 104H, SURFYNOL 104BC, SURFYNOL 104DPM, SURFYN0L 104PA, SURFYNOL 104PG-50, SURFYN0L 420 , SURFYN0L 440, SURFYN0L 465, SURFYN0L 485, SURFYNOL PSA-336 (all manufactured by Air · Products and Chemicals Co., Ltd.), etc. The oily pigment dispersion of the present invention can be used as the pigment composition of the present invention, 44 323045 201141957 organic solvent, A mixture of a dispersing agent or the like which is added as needed may be prepared by dispersing it by various dispersing agents. Further, various additives other than the above-mentioned raw materials may be added and dispersed as necessary, and the order of addition or addition of each raw material in preparing the pigment dispersion is not Particularly limited. In the oily pigment dispersion of the present invention, the content of the pigment composition is It is not particularly limited, and is preferably used in the range of 5 to 50% by weight, particularly preferably 10 to 40% by weight, based on the oil pigment dispersion. The type or content of the organic solvent used in the production of the oily pigment dispersion is The alcohol is not particularly limited, and examples thereof include alcohols such as methanol, ethanol, n-propanol, isopropanol, and n-butanol; acetone, methyl ethyl ketone, mercapto n-propyl ketone, mercapto isopropyl ketone, and anthracene; N-butyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, methyl isoamyl ketone, diethyl ketone, ethyl n-propyl ketone, ethyl isopropyl ketone, ethyl n-butyl Ketones such as ketone, ethyl isobutyl ketone, di-n-acetone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, isophorone; methyl acetate, ethyl acetate, n-propyl acetate , isopropyl acetate, n-butyl acetate, isobutyl acetate, hexyl acetate, octyl acetate, methyl lactate, propyl lactate, butyl lactate and other esters; ethylene glycol, diethylene glycol, triethyl Glycols such as diol, propylene glycol and dipropylene glycol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol single Propyl ether, ethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethyl Glycol ethers such as diol diethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monodecyl ether, dipropylene glycol monoethyl ether, dipropylene glycol dipropyl ether, tripropylene glycol monomethyl ether Ethylene glycol monomethyl ether acetate, ethylene glycol 45 323045 201141957 diethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoterpene Ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, two a diol acetate such as propylene glycol monomethyl ether acetate; a saturated hydrocarbon such as n-hexane, isohexane, n-decane, isodecane, dodecane or isododecane; p-hexene, heptene, Unsaturated hydrocarbons such as 1-Mulberry; cyclic saturated hydrocarbons such as cyclohexane, cycloheptane, cyclooctane, cyclodecane, decahydronaphthalene; cyclohexene Cycloheptene, cyclooctene, 1, 3, 5, 7-cyclooctatetraene (1,3,5,7.环状 (: 1 〇 0 (^ & 161 ^ 36116), cyclodequene (cyclodene) and other unsaturated hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene, etc. The content of the organic solvent is preferably The amount of the dispersing agent to be used in the production of the oily pigment dispersion is not particularly limited, and examples thereof include, for example,: a hydroxy-containing carboxylic acid ester, a long-chain polyamine decylamine with a high molecular weight acid ester salt, a high molecular weight polycarboxylic acid salt, a long-chain polyamine guanamine and a polar acid ester salt, a high molecular weight unsaturated acid ester Modified urethane, modified polyacrylate, condensate or salt of polyester having polyallylamine and free carboxylic acid, polyether ester type anionic surfactant, naphthalenesulfonic acid a salt of a morpholine condensate, a salt of an aromatic sulfonic acid morpholine condensate, a polyoxyalkylene methyl phosphate, a polyoxyethylidene phenyl ether, a stearylamine acetate, etc. One type may be used alone or in combination of plural kinds. The amount of use is not particularly limited, and it is preferably 5 to 30% by weight, more preferably 1 to 20% by weight in the oily pigment dispersion. 46 323045 201141957 The dispersing machine used in the production of the pigment dispersion of the present invention is not particularly limited, and for example, Type sand mill, vertical sand mill, annular bead mill, grinder, microfluidizer, high speed mixer, homomixer (h〇momixer), A homogenizer, a ball mill, a paint shaker, a roll mill, a ballast mill, an ultrasonic disperser, etc., can use a disperser or a mixer which is usually used for producing various dispersions. Before being dispersed by using various dispersers, it may be dispersed before being used in a training machine such as a kneader or a three-roll mill, or may be treated by solid dispersion such as a two-roll mill or the like. After the machine is dispersed, it is stored in a heating state of 30 to 80 ° C for several hours to one week for post-treatment, or by an ultrasonic disperser or a collision-type beadless disperser. The treatment step is effective for imparting dispersion stability to the pigment dispersion. Further, after being dispersed by various dispersers, it can also be treated by a centrifugal separator. This treatment can effectively remove the coarseness contained in the pigment dispersion. The inkjet ink of the present invention comprises any one of an aqueous ink using the above aqueous pigment dispersion and an oily ink using the above oily pigment dispersion. The aqueous inkjet ink of the present invention can be used in the present invention. The aqueous pigment dispersion of the invention is optionally produced by adding an aqueous medium, a resin, an interfacial activity (IV), other additives, etc., and mixing them uniformly. In the aqueous inkjet ink of the present invention, the content of the pigment composition is not particularly limited, and is preferably It accounts for 1% by weight, more preferably 2% to 7% by weight, in the aqueous inkjet ink. 323045 47 201141957 b The type or content of the aqueous medium used in the production of the aqueous ink ink is not particularly limited, and it is preferred to use ion exchange water or steamed water from which metal ions have been removed. The content of the aqueous medium is preferably from 60 to 99% by weight based on the water 嗔. , 'In addition, in order to prevent the black in the nozzle portion of the print head of the printer from drying and solidifying, and to make it discharge stably, the aqueous medium can also be used as a water-soluble solvent. The type of the water-soluble solvent is not particularly limited, and examples thereof include water-soluble solvents which are exemplified in the production of the aqueous pigment dispersion. These may be used alone or in combination of plural kinds. When such a water-soluble solvent is used, the content of the water-soluble solvent is preferably in the range of 1 to 50% by weight in the aqueous inkjet ink. Soil When the aqueous inkjet ink of the present invention is prepared, a resin can be used to impart a characterization to the pigment composition. The money of _ is not particularly limited, and examples thereof include a resin which can be used in the production of an aqueous pigment dispersion, or such an oil-in-water emulsion (emulsi〇n). Among these, the oil-in-water emulsion is a healthy, low-viscosity aqueous inkjet ink and a water-resistant recording material. These resins may be used singly or in combination of plural kinds. The content of the resins is preferably from water to ink, from 0.5 to 10% by weight of the ink-printed ink, more preferably from i to 5, if the content is: > at 0'5', the effect of fixing the pigment composition may be insufficient. 'If there are more than 15 subjects, there will be a problem that the ink is reduced or the discharge stability is lowered. These resins may also be reused by acidic functional groups such as ammonia, various amines, various inorganic tests, and the like. When the aqueous inkjet ink of the present invention is prepared, an interface agent 323045 48 201141957 active agent may be used as needed to impart dispersion stability to the pigment composition in the ink. The type of the surfactant is not particularly limited, and examples thereof include a surfactant which can be used in the production of an aqueous pigment dispersion. These surfactants may be used singly or in combination of plural kinds. The content of the surfactant is preferably from 5% to 5% by weight, more preferably from 5% to 5% by weight in the aqueous inkjet ink. When the aqueous inkjet ink of the present invention is produced, a drying accelerator, a penetrating agent, an antifungal agent, a chelating agent, and a conditioning agent may be used as other additives. In order to accelerate the drying of the aqueous inkjet ink at the time of printing, a drying accelerator can be used. The type of the drying accelerator is not particularly limited, and examples thereof include alcohols such as methanol, ethanol, and isopropyl alcohol. These may be used singly or in combination of plural kinds. Further, the content of these is preferably from 1 to 50% by weight based on the aqueous inkjet ink. Further, when the printed matter is a permeable substrate such as paper, various permeable agents can be used in order to promote the penetration of the ink onto the substrate and to accelerate the dryness of the surface. Examples of the penetrating agent include a water-soluble solvent such as diethylene glycol monobutyl ether or a diethylene glycol (external diol); in addition, a polyethylene glycol laurel test or sodium lauryl sulfate or sodium laurylbenzene sulfonate, A surfactant such as sodium oleate or sodium bis(2-ethylhexyl)sulfosuccinate. When the amount of use is 5% by weight or less in the aqueous inkjet ink, the effect is sufficient. If the amount is more than this amount, the viscosity of the ink may rise, or the ink may bleed out or cause offset. In order to prevent the generation of mildew in the aqueous inkjet ink, an anti-fungal agent can be used. The type of the anti-enzyme agent is not particularly limited, and for example, an anti-fungal agent which can be used in the production of an aqueous pigment dispersion of 323045 49 201141957 can be used. 0重量百分比的范围内使用。 The use of the aqueous ink is used in the range of 0.05 to 1.0% by weight. Soil In order to capture metal ions contained in the aqueous inkjet ink, and to prevent precipitation of insoluble substances in the nozzle portion of the print head of the printer or the ink, a chelating agent can be used. The type of the chelating agent is not particularly limited, and examples thereof include a sodium salt of ethylenediaminetetraacetic acid and ethylenediaminetetraacetic acid, a salt of ethylenediaminetetraacetic acid, a tetraammonium salt of ethylenediaminetetraacetic acid, and the like. These are preferably used in the range of from 0.005 to 5% by weight of the aqueous inkjet ink. The pH of the aqueous inkjet ink can be adjusted to a value of two corpses/evil, and various pH adjusters can be used. The type of the pH adjuster is not particularly limited, and examples thereof include a pH adjuster at the time of production of the aqueous (four) minutes. The oil-based inkjet ink of the present invention can be produced by adding an organic solvent, a resin, a dispersant, other additives, and the like as necessary in the oily pigment dispersion of the present invention, and mixing them uniformly. In the inkjet ink of the present invention, the content of the pigment composition is particularly limited to, preferably, the i% by weight of the oil-based inkjet ink, more preferably 2 to 7% by weight. The type of the organic solvent used in the production of the oil-based inkjet ink is not particularly limited. For example, an organic solvent usable in the production of an oily pigment dispersion can be used. The content of the organic solvent is not particularly limited, and is preferably from 8 Q to 97% by weight in the oil-based inkjet ink. These organic solvents may be used singly or in combination of plural kinds. In the case of the oil-based inkjet ink of the present invention, a resin can be used to impart a characterization of the pigment composition to the object to be printed. The type of the resin is not particularly limited to 323045 50 201141957, and examples thereof include petroleum resin, casein, shellac, rosin resin, rosin ester resin, cellulose resin, natural rubber, synthetic rubber, and ring. Rubber, gasified rubber, oxidized rubber, hydrochloric acid rubber, phenolic resin, terpene phenol resin, alkyd resin, polyester resin, unsaturated polyester resin, amine resin, epoxy resin, vinyl resin, poly Chloroethylene, polyallylamine resin, chloroacetic acid-ethyl acetate resin, ethyl acetate ethyl acetate, resin, vinylidene chloride resin, acrylic resin, methacrylic acid Resin, urethane resin, polyoxyn epoxide, fluororesin, drying oil, synthetic drying oil, maleic acid resin, polyamide resin, polyimine resin, benzoxamine resin, melamine resin, Urea resin, butyral resin, coumarone-indene resin, xylene resin, fumarate resin, polysulfate, polypropylene, wax-latex resin, styrene - Acrylic resin, styrene-maleic acid resin, and the like. These may be used singly or in combination of plural kinds. The amount of use is not particularly limited, and is preferably from 1 to 15% by weight, more preferably from 3 to 8% by weight, based on the oil-based inkjet ink. When the oil-based inkjet ink of the present invention is prepared, a dispersant may be used as needed to impart dispersion stability to the pigment composition in the ink. The type of the dispersant is not particularly limited, and examples thereof include a dispersant which can be used in the production of an oily pigment dispersion. These may be used singly or in combination of plural kinds. 5至十重量百分比。 The amount of the use of the oil-based inkjet ink is 0. 1 to 15% by weight, more preferably 0.5 to 10% by weight. The oil-based inkjet ink of the present invention may further contain an additive. Examples of the addition of 51 323045 201141957 include a wetting agent, a deaerator/defoaming agent, a preservative, and an antioxidant. When the above-mentioned raw materials are mixed to prepare an ink jet ink, the method of mixing the raw materials is not particularly limited, and it can be carried out by using a high-speed disperser or an emulsifier in addition to a stirrer which is usually agitated with a stirring blade. In this case, the order of addition of the raw materials, the mixing method, and the like are not particularly limited. Further, the ink jet ink prepared by mixing the respective raw materials can be filtered by various filters to remove coarse particles contained in the ink. The pore diameter of the filter to be used at this time is preferably l#m or less, more preferably not more than 0.65. The colored resin composition of the present invention contains the pigment composition of the present invention, a binder resin, a charge control agent, a release agent, etc., which will be described later, and can be used as a toner for electrophotography. The colored resin composition of the present invention can be prepared by thoroughly mixing the pigment composition of the present invention and a binder resin by a mixer, followed by melt-kneading by a hot kneader, and then cooling and solidifying. The content of the pigment composition is not particularly limited, but is preferably used in the range of 10 to 80% by weight in the colored resin composition. It is particularly preferably from 20 to 60% by weight. The content of the binder resin is not particularly limited, and it is preferably used in the range of 20 to 90% by weight in the composition of the colored resin. Particularly preferred is 40 to 80% by weight. The toner for electrophotographic use of the present invention (in the present specification, the toner for electrophotographic image may be simply referred to as a toner) may be produced by a conventionally known production method such as a pulverization method or various polymerization methods. In the production example by the pulverization method, the colored resin composition can be pulverized by various pulverizers by using various pulverizers, and then mixed with additives other than those described later, and then finely pulverized and classified. Manufacturing. On the other hand, in the production example by the polymerization method, the pigment composition, the polymerization initiator, and optionally various additives of the present invention can be dissolved and dispersed in a monomer to prepare an oil phase. The oil phase is then mixed with the aqueous phase containing the dispersant to produce/radically polymerize. Then, it is washed, dried, and then mixed with an external additive, whereby a toner can be produced. When the toner of the present invention is produced by a polymerization method, it can be produced by a conventionally known method such as a suspension polymerization method, an emulsion polymerization method, a dissolution suspension method, or an ester elongation polymerization method. Further, when the toner is produced by these polymerization methods, the colored resin composition described above can be used as a raw material for processing. The binder resin to be used in the production of the enamel resin composition and the toner of the present invention is not particularly limited, and examples thereof include styrene __p-chlorophenothrene copolymer, styrene-vinyl toluene copolymer, and Styrene-vinyl naphthalene copolymer, styrene-acrylate copolymer, styrene-mercapto acrylate copolymer, styrene gas methyl propionate beer copolymer, stupid ethylene-acrylonitrile copolymer, benzene Ethylene-vinyl methyl ether copolymer, styrene-vinyl ethyl ether co-I, present ethylene-vinyl methyl ketone copolymer, stupid ethylene butadiene dilute copolymer, styrene-isoprene Copolymer, styrene-acrylonitrile-ruthenium copolymer, polystyrene, phenolic resin, natural modified phenolic resin, natural resin modified maleic acid resin, acrylic resin, methacrylic resin, polyvinyl acetate, Polyoxyphthalic resin, polyester resin, polyurethane, polyamide resin, furan resin, epoxy resin, diphenyl benzene resin, polyvinyl butyral, terpene resin, stupid furan oxime resin, Petroleum resin, etc. In 323045 53 201141957, a polyester resin and a styrene copolymer are preferably used. The composition of the present invention is particularly excellent in the suitability of the (four) resin in the above-mentioned resin-reducing material. The pigment composition is preferably dispersed and finely dispersed in the binder resin. Examples of the alcohol component constituting the polysodium sulfonate include ethylene dipropylene glycol, u-propylene glycol, u, butanediol, i-butylene glycol, 2,3-butanediol, and a dilute diol. Ethylene glycol, triethylene glycol, U-pentanediol, U-hexadiene- 4 (I-methyl), and a double-fermented organism such as a double-riding organism represented by the following formula (9); Polyols such as glycerin, diglycerin, sorbitol, sorbitan, tributol, dimercapto-Wei, pentaerythritol, dipentaerythritol, dipentaerythritol, etc., which may be used alone or Two or more types can be used in combination.

(In the formula, Ra is an extended ethyl group or a stretching propyl x+y is 2 to 1 Å). X and y are each an integer of 1 or more, and the acid component constituting the polyester resin, dibasic acid di-t-acid, terephthalic acid, and nitrous acid (four) species - " · neighbors" of the present-formic acid, 郴本二Aromatically known amphiphiles such as formic anhydride or its bismuth; glyceric acid, adipic acid, azelaic acid, bismuth:: family: carboxylic acids or their anhydrides; and further alkyl groups having a carbon number of 16 to 18 "j acid or its anhydride ; fumaric acid, maleic acid, pyrocitric acid, itaconic acid, etc. 323045 54 201141957 No more than two or its anhydride. As a cross-linking component, the heat of the triterpenoids can be exemplified by trimellitic acid, pyromellitic acid, naphthalene tricarboxylic acid, and tributylacetate. A)-hexyl dicarboxylic acid, monophenylketone tetradecanoic acid And tetrakis (methylene methane octane tetracarboxylic acid, diphenyl ketone tetracarboxylic acid or its anhydride, etc.. Q: used alone or in combination with a plurality of species. Polyeucalyptus can be used alone from the above alcohol component The homopolyester or the copolyester synthesized by the acid component may be used in combination of two or more kinds. / In addition, from the viewpoint of offset resistance and low-temperature fixability, the polyester resin is impregnated with the gel. The weight average molecular weight (Mw) in the molecular weight measured by the layer analysis method is preferably 5 or more, more preferably 10,000 to 1,000 '000. Particularly preferably the weight average molecular weight (5)) To the extent of 100,000. When the weight average molecular weight of the polyester resin is small, the molecular weight of the toner having a reduced offset resistance tends to increase, and the fixing property tends to be lowered. Further, the acid value of the polyester resin is preferably from 5 to 6 mg/g, more preferably from 10 to 55 mgKOH/g. When the acid value is less than 5 ing K 〇 H / g, the release agent sometimes liberates. On the other hand, when the acid value exceeds 6 〇 mg K 〇 H / g, the image density may be lowered in a high-humidity environment due to the hydrophilicity of the resin. The hydroxyl value of the polyester resin is preferably 7 〇 mg K 〇 H / g or less, more preferably 50 mg KOH / g or less. When the valence of the hydroxyl group exceeds 70 mg K 〇 H / g, the hydrophilicity may become large and the image density may be lowered in a high-humidity environment. Further, from the viewpoint of preventing agglomeration of the toner, the glass transition temperature (Tg) of the polyester resin using a differential scanning calorimeter (device: DSC-6' manufactured by Shimadzu Corporation) is preferably 50 to 7 (TC, more Good for 50 to 'King' (10) C 〇

S 323045 55 201141957 In the toner of the present invention, a charge control agent may be added as needed. By using a charge control agent, a toner having a stable charge can be obtained. In the toner of the present invention, any one of conventionally known positive or negative charge control agents can be used as the charge control agent. When the toner of the present invention is a positively chargeable toner, examples of the positive charge control agent to be used include nigrosine dyes, triphenylmethane dyes, organic tin oxides, and grade 4 The ammonium salt compound and a styrene/acrylic polymer which is copolymerized with a quaternary ammonium salt as a functional group in a styrene/acrylic resin are preferably a quaternary ammonium salt compound. The quaternary ammonium salt compound usable in the present invention may, for example, be a salt-forming compound composed of a quaternary ammonium salt and an organic sulfonic acid or molybdic acid. The organic sulfonic acid is preferably naphthalenesulfonic acid. On the other hand, when it is a negatively chargeable toner, examples of the negative charge control agent include a metal complex of a monoazo dye, and a copolymerization of a sulfonic acid as a functional group to a styrene-acrylic resin. A styrene-acrylic polymer, a metal salt compound of an aromatic hydroxycarboxylic acid, a metal complex of an aromatic hydroxycarboxylic acid, a condensate, a squama compound, and the like. The aromatic carboxylic acid is preferably salicylic acid, 3, 5-di-t-butyl salicylic acid, 3-hydroxy-2-naphthoic acid or 3-phenylsalicylic acid. Further, the metal used for the metal salt compound may be exemplified by zinc, about, town, ruthenium, and the like. Further, a release agent can be used in the toner of the present invention. Examples of the release agent include a hydrocarbon butterfly such as a polypropylene crucible, a polyethylene crucible, or a fischer-tropsch wax; a synthetic ester butterfly; a natural ester system such as carnauba wax or rice wax. Waxes, etc. 56 323045 201141957 In the toner of the present invention, an external additive such as a lubricant, a fluidizing agent, an abrasive, a conductivity imparting agent, or an image peeling preventing agent may be used as needed. As the external additive, any of the known additives other than those conventionally used in the production of the toner can be used. Examples of such external additives include the following. Examples of the lubricant include polyvinylidene fluoride and zinc stearate; and the fluidizing agent may be exemplified by a dry process or a wet process, such as sulphur dioxide, oxidized, titanium oxide, orthopedic co-oxide, and stone eve. Titanium co-oxides and the like which are treated by hydrophobization. In addition, examples of the polishing agent include cerium nitride, cerium oxide, cerium carbide, barium titanate, tungsten carbide, calcium carbonate, and the like, and the like. The conductivity imparting agent may, for example, be tin oxide. As the fluidizing agent used in the toner of the present invention, in the above-mentioned examples, it is preferred to use a hydrophobized ceria, a yttrium aluminum co-oxide, and a niobium-titanium co-oxide fine powder. The hydrophobization treatment method of the fine powders may be carried out by using an oil-repellent agent such as eucalyptus oil, tetramethyldiazane, dimethyldichlorosilane or dimethylmercaptoin. The toner of the present invention can be used as a single component developer, or can be used as a one component developer in combination with a carrier. The carrier for the two-component developer can also be used in any of the conventionally known ones. Examples thereof include iron powder, ferrite powder, magnetic powder of nickel powder, and the like, or those having a surface treated with a resin or the like. The resin covering the surface of the carrier may, for example, be a styrene-enedonate copolymer, styrene, a methyl acrylate copolymer, an acrylate copolymer, a methacrylate copolymer, a fluorine-containing resin, or a poly Dream oxygen resin, polyamine resin, ionic polymer resin, polyphenylene sulfide resin, etc., or a mixture thereof. 323045 57 201141957 Among these, the resin containing polyoxymethylene is particularly preferable because it forms less toner waste. The weight average particle diameter of the carriers is preferably in the range of from 3 Å to 100 /z m. When the colored resin composition of the present invention is produced, the mixer used for mixing various raw materials may be any conventionally known mixer such as a Henschel mixer or a super mixer (SUper miXer). In addition, the kneading machine used for the melt-kneading can also use a batch kneader such as a heating kneader or a Banbury mixer (also: a 1-axis or 2-axis extrusion). Continuous kneading machine such as extruder. When the edge-colored resin is formed, the temperature of the various materials for melt-kneading is preferably from 100 to 20 (TC, more preferably from 120 to 18 (TC. When not up to ι, the pigment and/or pigment composition) The dispersion may be insufficient. When it exceeds 2 Torr, the binder resin may be thermally degraded. The charge control agent may be mixed with various raw materials in the above melt-kneading step, and may be mixed and used after preparing the colored resin composition. Alternatively, it may be further mixed (4) after mixing, and in the step of the shaft mixing, (4), since the charge control agent can be self-dispersing in the composition, it is preferable. Similarly, in the above-mentioned smelting step, various original batches can be combined, and the coloring tree of the village (four) can be mixed and used, or can be used again after mixing and mixing. In the case of use, it is preferable to obtain a toner having high durability. 323045 58 201141957 [Examples] Hereinafter, the present invention will be described in detail by way of examples, but the present invention is not limited thereto. Pigment group of the invention The product is described in detail. <Preparation of monoazo pigment and pigment composition> Production Example 1 &lt;Preparation of monoazo pigment A (c. ment. Pigment Yeii〇w 74)&gt; 2-methoxy-h cis phenylamine 67. 3g was added to water _g to mix the suspension with water, and then add ice to adjust the temperature to 5 C or less. Then add 35% hydrochloric acid i^g to the suspension. While stirring for 5 hours, the mixture was stirred for 1 hour. Then, an aqueous solution in which 72. Og of sodium nitrite was dissolved in 72. Og was added to the suspension, and stirred for a few hours to carry out diazotization. 5克和。 The reaction mixture was added 5 g of sulfamate sulfonate to reduce the nitrous oxide to prepare a diazolium (diaz〇nium) aqueous solution. On the other hand, as a coupling agent component of o-acetyl oxime aniline 84. 5g and 164 g of a 25% aqueous sodium hydroxide solution was added to water i4 g, and the mixture was dissolved to dissolve completely. The resulting aqueous solution was poured into an aqueous solution containing 80.0% acetic acid and 80.2 g of water and 420 g of water to prepare a coupling agent slurry. The above prepared coupling agent slurry was heated to 4 Torr. (:, in which 1 hour was added dropwise with heavy nitrogen rust After the completion of the dropwise addition, the reaction was terminated by stirring at the same temperature for 1 hour. After the completion of the reaction, the slurry was heated to 9 Torr and stirred for 1 hour, and then filtered using a Buchner funnel having a diameter of 285 mm. The filter residue was washed with 25 liters of ion-exchanged water, and then dried and pulverized to obtain 150 μg of CI Pigment Yellow 74. 59 323045 201141957 Production Example 2 &lt;Modulation of Mono- Evening Pigment B (CIPigment) Yell〇w ι)&gt; The 6-methoxy-4-nitroaniline used in the production example 1 was changed to 4-mercapto-2-nitroaniline 60·9g, and As the coupling agent component, o-acetamethylene ethoxy aniline 84. 5g was changed to acetanilide 72. The remainder was obtained in the same manner as in Production Example 1, to obtain CI Pigment Yellow l. 132g. Production Example 3 <Preparation of a single gas pigment c (c. I. Pipaent Yellow 9)> Each of 2-methoxy-4-nitroaniline used as a diazo component in Production Example 1 was changed to 67. 3 g. 4-methyl-2-nitroaniline 60. 9g, and the o-acetamidine methoxy sulfoxime 84·5g used as a coupling agent component was changed to N-ethyl ethanoyl o-amylamine 78. 〇g The rest was obtained in the same manner as in Production Example 1 to obtain 137 g of monoazo pigment C (cI Pigment Yellow 9). Production Example 4 &lt;Preparation of monoazo pigment D (CIPigment Yellow 73)&gt; 67.3 g of 2-methoxy-4-inolide was used as a diazo component in Production Example 1 to 4-chloro-2 69.0 g of nifedipine was used, and in the same manner as in Production Example 1, 151 g of monoazo pigment D (c. I pigment Yell〇w 73) was obtained. Example 5 &lt;. Weekly monoazo pigment E (ci pigment YeH〇w 105) &gt; 67.3 g of 2-methoxy-4-nitroaniline used as a diazo component in Production Example 1 was changed to 6-amino group_7_chlorine_ 4_Methylquinoline-2(1H)-one ketone 83·4g' The remainder was obtained in the same manner as in the production example, to obtain a single-equivalent pigment E(C·I. Pigment Yell〇wi〇5)i65g. Production Example 6 &lt;Preparation of monoazo pigment KC.I. Pigment Yellow 213) 323045 60 201141957 &gt; Each of 2-methoxy-4-nitroaniline used as a diazo component in Production Example 1 was changed to 67. 3g. 5克为为N-(7-methoxy-2, 3-二。 The amine-terephthalic acid dinonyl ester 83. 7g, and used as a coupling agent component of o-acetamidine methoxy sulfonamide 84. 5g changed to N- (7-methoxy-2, 3- two 119 g of pendant oxy-1,2,3,4-tetrahydroquinoxalin-6-yl)-3-oxobutylbutanamine, and the same procedure as in Production Example 1 was carried out to obtain monoazo pigment F. (CIPigment Yellow 213) 198g. 5g。 The powder of the monoazo pigment derivative A of the following formula: 6. 5g The mixture was uniformly mixed to obtain a pigment composition A 100 g. Omol%。 The content of the mono azo pigment derivative A is 5. Omol%. Among them, the monoazo pigment derivative A shown by the following formula was obtained by the same method as in Production Example 1.

Monoazo pigment derivative A

Conh(ch2&gt;3n(c2h5)2 Example 2 &lt;Preparation of Pigment Composition B&gt; The monoazo pigment A (CI Pigment Yellow 74) prepared in Production Example 1 was 93.lg and the monoazo represented by the following formula The singularity of the following formula is shown in the following formula: The content of the mono azo pigment derivative B in the pigment composition B is 5. Omol%. The azo pigment derivative B was obtained by the same method as in Production Example 1 in 61 323045 201141957.

Monoazo pigment derivative B

Example 3 &lt;Preparation of the pigment composition C&gt; The monoazo pigment B (CI Pigment Yellow 1) prepared in Production Example 2 was 89. 3g and a powder of the monoazo pigment derivative C represented by the following formula. 7 g was uniformly mixed to obtain a pigment composition C 100 g. Omol%。 The content of the mono azo pigment derivative C is 5. Omol%. Among them, the monoazo pigment derivative C represented by the following formula was obtained by the same method as in Production Example 2. Monoazo pigment derivative C no2 h3c

Coch3 N=N-CHCONH

o (ch2) 2n (c4h9) 2 Example 4 &lt;Preparation of pigment composition D&gt; The monoazo pigment C (CI Pigment Yellow 9) prepared in Production Example 3 was 93.2 g and the monoazo represented by the following formula 6.8 g of the powder of the pigment derivative D was uniformly mixed to obtain a pigment composition D 100 g. The content of the monoazo pigment derivative D is 5. Omo 1%. Among them, the monoazo pigment derivative D represented by the following formula was obtained by the same method as in Production Example 3.

Monoazo pigment derivative D 62 323045 201141957

Example 5 &lt;Preparation of Pigment Composition Mound&gt; The single azo pigment D (CI Pigment Yellow 73) prepared in Production Example 4 was 93.4 g and a powder of a monoazo pigment derivative E represented by the following formula. 6 g was uniformly mixed to obtain a pigment composition E 100 g. The content of the monoazo pigment derivative E is 5. Omo 1%. Among them, the monoazo pigment derivative E represented by the following formula was obtained by the same method as in Production Example 4.

Monoazo pigment derivative E

S02NH(CH2)3N(CH3)2 Example 6 &lt;Preparation of pigment composition F&gt; The monoazo pigment E (CI Pigment Yellow 105) prepared in Production Example 5 was 92.lg and the monoazo represented by the following formula 7.9 g of the powder of the pigment derivative F was uniformly mixed to obtain a pigment composition F 100 g. Omol%。 The content of the mono- ing I pigment derivative F is 5. Omol%. Among them, the monoazo pigment derivative F represented by the following formula was obtained by the same method as in Production Example 5. Monoazo pigment derivative

Coch3 N=N—CHCONH

NH(CH2)3N(C4H9)2 N

: OH 63 323045 201141957 Example 7 &lt;Preparation of pigment composition 0&gt; The monoazo pigment F (CI Pigment Ye 11 ow 213) prepared in Preparation Example 6 was 94. 6 g and derived from a mono-noodle pigment represented by the following formula: The powder of the material G was 5. 4 g uniformly mixed to obtain a pigment composition G 100 g. Omol%。 The content of the mono azo pigment derivative G is 5. Omol%. Among them, the monoazo pigment derivative G represented by the following formula was obtained by the same method as in Production Example 6.

Monoazo pigment derivative G

Example 8 &lt;Preparation of Pigment Composition H&gt; The monoazo pigment A (CIPigment Yellow 74) prepared in Production Example 1 was 280.4 g, the monoazo pigment derivative A 19.6 g, sodium chloride 1500 g, and A mixture of ethylene glycol 250 g was kneaded at 60 ° C for 6 hours using a stainless steel one-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) to obtain a clay-like kneaded product. Then, the kneaded product was placed in 15 liters of warm water, and heated to 70 ° C while stirring for 1 hour to form a slurry. The slurry was then divided into 3 equal portions and then transitioned separately using a 285 mm diameter Buchner funnel. Wash the filter residue with 15 liters of warm water at 50 °C. Then, the residue was taken out, and it was added to an aqueous solution containing 250 g of 35% hydrochloric acid and 15 liters of tap water, and the slurry was turbulent. After stirring for 1 hour, the slurry was divided into 3 equal portions and then separately filtered using a Buchner funnel having a diameter of 285 匪 64 323045 201141957. The job search is not as good as the water supply. Weaving the filter wire and adding it to the ionic liters of the liters of the liters and changing the water. After 1 hour, the slurry was divided into 3 equal portions, and then the Buchner funnel with a diameter of 285 was used to shout. Then, 15 liters of ion-exchanged water was sprayed on the slits, and then dried and pulverized to obtain 230 g of the leg composition. The content of the monoazo pigment derivative cerium in the group was 5. Omol%. Example 9 &lt;Preparation of Pigment Composition I> The monoazo pigment A (CIPigment Yellow 74) prepared in Production Example 1 was 28 G.4 g, the monoazo pigment derivative A 19 6 g, sodium chloride 1500 g, and A mixture of 25 g of ethylene glycol was kneaded at 6 〇〇c for 6 hours using a stainless steel kneading kneader (manufactured by Inoue Seisakusho Co., Ltd.) to obtain a clay-like kneaded product. Then, the kneaded product was placed in 15 liters of warm water, and heated to 70 ° C while stirring for a few hours to make it into a slurry. The slurry was then divided into 3 equal portions and then filtered using a 285 mm diameter Buchner leak. 15 liters of the filter residue was washed, and then dried and pulverized to obtain 4 235 g of a pigment composition. The monoazo pigment derivative in the pigment composition I was 5. Omol%. The change of the monoazo pigments 19.6g was changed to 279.4g of the monoazo pigment A (C i η Yellow 74) used in the example 8 was changed. The monoazo pigment derivative B 2 〇. 6 g was obtained in the same manner as in Example 323045 65 201141957 8 to obtain a pigment composition J 230 g. Omol%。 The content of the mono azo pigment derivative B is 5. Omol%. Example 11 &lt;Preparation of Pigment Composition K&gt; The monoazo pigment A (CI Pigment Yellow 74) used in Example 9 was changed to 289.4 g, and the monoazo pigment derivative A 19.6 g was changed to The monoazo pigment derivative B 20.6 g was obtained in the same manner as in Example 9 to obtain a pigment composition K 234 g. Omol%。 The content of the mono azo pigment derivative B is 5. Omol%. Example of the following formula: &lt;Preparation of the pigment composition L&gt; The acetophenone methoxy aniline used as the coupling agent component in the production example 1 8.4. 5g was changed to o-acetamidine methoxyaniline 80. 3g and the following formula A mixture of the ethyl acetanilide compound A 6. shown was used, and in the same manner as in Production Example 1, a pigment composition L 152 g was obtained. The content of the monoazo pigment derivative A is 5.0 mol%. The content of the monoazo pigment derivative A is 5.0 mol%.

Acetyl anilide compound A

COCH3 CH2CONH

CONH(CH2)3N(C2H5)2 Example 13 &lt;Preparation of pigment composition M&gt; The o-acetamidine methoxyaniline used as the coupling agent component in Production Example 1 was changed to 84. 5g to o-acetamidine methoxy A mixture of aniline 84. 4 g and acetamidine anilide compound A 0. 068 g was obtained in the same manner as in Production Example 1, to obtain a pigment composition M 150 g. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. Example 1 &lt;Preparation of the pigment composition N&gt; The o-acetyl oxime anilide used as the coupling agent component in Production Example 1 was changed to 84. 5g to o-ethoxime anilide 84. lg and acetamidine A mixture of aniline compound A 0. 68 g was obtained in the same manner as in Production Example 1, to obtain a pigment composition N 150 g. The content of the monoazo pigment derivative A is 0. 5Omo 1 %. The content of the mono azo pigment derivative A is 0. 5Omo 1 %. 5克和乙醯乙醯 实施 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 调制 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 71 A mixture of aniline compound A 20.4 g was obtained in the same manner as in Production Example 1, to obtain a pigment composition of 0 157 g. Omol%。 The content of the mono azo pigment derivative A is 15. Omol%. The content of the monoazo pigment derivative A is 15. Omol%. </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> A mixture of aniline compound A 40. 8 g was obtained in the same manner as in Production Example 1, to obtain a pigment composition P 165 g. Omol%。 The content of the monoazo pigment A is 30. Omol%. The content of the monoazo pigment derivative A is 30. Omol%. Example 17 &lt;Preparation of Pigment Composition Q&gt; 67 323045 201141957 The o-acetamethylene oxyaniline used as the coupling agent component in Production Example 1 was changed to 84. 5g to o-acetamidine methoxyaniline 42. A mixture of acetanilide compound A 68. Og was obtained in the same manner as in Production Example 1, to obtain a pigment composition Q 174 g. The content of the pigment composition Q contained in the monoazo pigment A (C.I. Pigment Yellow 74) and the monoazo pigment derivative A 'monoazo pigment derivative a was 50. 〇m〇i%. Example of the following: </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; A mixture of acetamidine anilide compound β 7.4 g of the formula shown in the formula was obtained in the same manner as in Production Example 1, to obtain a pigment composition R 152 g. The content of the monoazo pigment derivative β is 5.0 mol%. The content of the monoazo pigment derivative β is 5.0 mol%.

Acetyl aniline compound B

。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 A mixture of 0.074 g of acetanilide compound B was used, and the pigment composition S 150 g was obtained in the same manner as in the production example. The content of the pigment composition s contained in the monoazo pigment A (C.I. Pigment Yellow 74) and the monoazo pigment derivative B' monoazo pigment derivative β was 〇. 05 m〇1%. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 A mixture of acetanilide compound B 0. 74 g was used, and in the same manner as in Production Example 1, a pigment composition T 150 g was obtained. The content of the monoazo pigment derivative B is 0. 5mo 1 %. The content of the monoazo pigment derivative B is 0. 5mo 1 %. </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> A mixture of anthranilamide compound B 22. 2 g was obtained in the same manner as in Production Example 1, to obtain a pigment composition U 157 g. The content of the monoazo pigment derivative B is 15. 0 mol ° / 〇. The content of the mono azo pigment derivative B is 15. 0 mol ° / 〇. Example </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> A mixture of aniline compound B 44. 3 g was obtained in the same manner as in Production Example 1, to obtain a pigment composition V 166 g. Omol 1%。 The content of the mono azo pigment derivative B is 30. Omo 1%. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 69 323045 201141957 A mixture of aniline compound B 73. 9 g, the remainder was obtained in the same manner as in Production Example 1, to obtain a pigment composition W 175 g. Omol 1%。 The content of the mono azo pigment derivative B is 50. Omo 1%. Example 2 &lt;Preparation of the pigment composition X&gt; 6 g of 2-methoxy-4-nitroaniline used as a diazonium component in Production Example 1 was changed to 4-chloro-2-mercaptoaniline 56. 6 g, and 5克与一种一种例如为为。 The acetophenone acetophenone used as a coupling agent component 84. 5g was changed to 4'-gas-2', 5'-dimethoxyethoxyacetamidine aniline 105. 3g and the following formula A mixture of acetamidine anilide compound Η 7. Og was obtained in the same manner as in Production Example 1, to obtain a pigment composition X 166 g. The content of the mono azo pigment derivative Η is 5. Omo 1 %. The content of the mono azo pigment derivative Η. Acetyl aniline compound Η coch3 ch2conh

CONH(CH2)3N

Monoazo pigment derivative

Example 25 &lt;Preparation of Pigment Composition Υ&gt; 6-glyoxy-4-nitroaniline used as a diazo component in Production Example 1 was changed to 4-amino-3-indolyloxy-indole-benzene. Benzene sulfonamide 111. 3g, and the o-acetamidine methoxyaniline 70 323045 201141957 84. 5g used as a coupling agent component was changed to 4' • Chloro-2,5'-di-f-oxyethyl hydrazine A mixture of 3 g of acetamidine and a compound of acetamidine compound I 8 · 4 g represented by the following formula was obtained in the same manner as in Production Example 1, to obtain a pigment composition Y. The content of the mono azo pigment derivative 1 is 5. Omol%. The content of the monoazo pigment derivative 1 is 5. Omol%.

Ethyl anilide compound I iH2CONH-^^S02NH-^Vs〇2NH2 monoazo pigment derivative I PCH3

C6H5HN〇2S

Coch3 =N-CHCONH so2nh

So2nh2 Example 26 &lt;Preparation of pigment composition z&gt; 84.5 g of o-acetamidine methoxyaniline used as a coupling agent component in Production Example 1 was changed to 5,-chloro-2,-methoxyethionanilide A mixture of 93.7 g and an acetanilide compound J 10.7g represented by the following formula was obtained in the same manner as in Production Example 1, to obtain a pigment composition Z169g. The pigment composition Z contains a component of C. I. Pigment Yellow 111 and a monoazo derivative of the following formula! Omol%。 The content of the mono azo (four) enchantment J is 5. Omol%.乙乙乙苯胺化合物 j 71 323045 201141957 COCH3 Γ- ch2c〇nh-^

NH(CH2)3N(C2H5)2 nh(ch2&gt;3n(c2h5)2

Monoazo pigment derivative J

COCH3 N=N—CHCONH

NH(CH2)3N(C2H5)2 nh(ch2&gt;3n(c2h5)2 Example 27 &lt;Preparation of pigment composition a&gt; 2-methoxy-4-nitroaniline 67 used as a diazo component in Production Example 1 5克改为为为为5乙乙乙ethoxyphene 84. 5g was changed to 5-aminoisoindoline-1,3_dione 64. 8g, and used as a coupling agent component.

2,4,-Dimethylethylene aniline 79·5 g and a hexamethylene anilide compound A 6 8 g of a solid compound were obtained in the same manner as in Production Example 1, to obtain a pigment composition a 149 g. The composition of the pigment composition a is C. I. Pigment

Yellow 167 and the monoazo pigment derivative K represented by the following formula, the content of the monoazo pigment derivative K is 5. ΟιηόΓ ° / 〆

Coch3 N=N—CHCONH monoazo pigment derivative Κ 〇 h

CONH(CH2)3N(C2H5&gt;2 Example 28 &lt;Preparation of pigment composition b&gt; 2-methoxy-4-phenylaniline 67·3g as a diazo component was added to 72 323045 201141957 water 501⁄2, and was carried out The suspension was prepared by stirring, and the temperature was adjusted to 5 ° C or less by adding ice. Then, hydrochloric acid 1 () was added to the suspension, and the mixture was stirred for 5 hours while maintaining the temperature of 5 ° C or less. Then, it was added to the suspension at 72 ° C. Og water was added with sodium nitrite 28. 水溶液g to prepare an aqueous solution, and stirred for 1 hour, thereby diazotization. Add 5 g of sulfamate to the reaction mixture to make nitrous acid disappear, and the weight was adjusted. An aqueous solution of hydrazine was added to the aqueous solution of diazonium in an aqueous solution of hexamethylene anilide A 6. 8 g and mixed for 10 minutes to react a part of the diazonium rust compound with acetamidine aniline compound A to obtain a single The diazonium hydrazine aqueous solution of the azo pigment derivative A. On the other hand, 80 g of o-acetamidine methoxyaniline as a coupling agent component and i64 g of a 25% aqueous sodium hydroxide solution were added to 140 g of water, and stirred. Completely dissolved. Inject the resulting aqueous solution into the mixture. A coupling agent slurry was prepared in an aqueous solution of 80% acetic acid (82.0 g) and water (420 g). The prepared coupling agent slurry was heated to 4 (TC, in which an aqueous solution of diazo rust containing monoazo pigment derivative A was added dropwise over 1 hour. After the completion of the dropwise addition, the reaction was terminated by stirring at this temperature for 1 hour. After the completion of the reaction, the slurry was heated to 90 ° C and stirred for 1 hour, and then filtered using a Buchner funnel having a diameter of 285 Å. The ion exchange was carried out on the filter residue. 25 liters of water was washed, and then dried and pulverized to obtain 150 g of the pigment composition b. The pigment composition b contained a component of monoazo pigment a (CIPigment Yellow 74) and a monoazo pigment derivative a, The content of the monoazo pigment derivative A was 5.0 mol%. Example 29 &lt;Preparation of pigment composition c&gt; The ethyl acetophenone compound A 6·8g in Example 28 was changed to s 73 323045 201141957 Indole anilide compound B 7.4 g, and the same procedure as in Example 28 was carried out to obtain a pigment composition c 150 g. The pigment composition c contained a component of monoazo pigment A (CI Pigment Yeu〇w 74) and a single couple. Nitrogen pigment derivatization B, the content of the monoazo pigment derivative B was 5. 〇m 〇 1%. Example 30 &lt;Preparation of pigment composition d&gt; 6-9 g of 2-decyloxy_4_salbenylamine as a diazo component was added. The mixture was stirred and mixed with water to prepare a suspension, and ice was added thereto to adjust the temperature to 5 C or less. Then, 35% hydrochloric acid was added to the suspension, and the mixture was stirred for 1 hour while maintaining the generation. Then, an aqueous solution prepared by adding sodium nitrite 28 〇g to 72·Og of water was added to the suspension to disturb for 1 hour, and this was linearized. To the reaction mixture, 2 sour was added to make the yttrium acid disappear, and an aqueous solution of diazo rust was prepared. Then, a mono-anthraquinone pigment derivative A i ().3g was added to the aqueous solution of turbid cadmium and the solution was homogeneous. h There is a heavy gas recording of the early rat pigment derivative A. The o-acetamidine methoxy sulfonamide (10) and the aqueous solution of the occupational oxidation surface are added as a coupling agent, and are completely dissolved. Further, the obtained aqueous solution was poured into an aqueous solution of 82. g and water g to prepare a coupling agent slurry. ^ The above-mentioned prepared coupling agent slurry was heated to the muscle, and an aqueous solution of money rust containing the monovalent pigment derivative A was added dropwise thereto. After the completion of the dropwise addition, the reaction was terminated by directly mixing the mixture for 1 hour. At the end of the reaction, the Buchner funnel with a diameter of 285 mm was used for the passage.对,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, The content of the monoazo pigment A (CI Pigment Yellow 74) and the monoazo pigment derivative A, the monoazo pigment derivative A was 5.0 mol%. Example 31 &lt;Preparation of pigment composition e&gt; Example 30 The monoazo pigment derivative A 10.3g was changed to the monoazo pigment derivative B 10.8g, and the pigment composition e 150g was obtained in the same manner as in Example 30. The pigment composition e contained The composition is a monoazo pigment A (CI Pigment Yellow 74) and a monoazo pigment derivative B, and the content of the monoazo pigment derivative B is 5.0 mol%. Example 32 &lt;Preparation of pigment composition f&gt; In Example 30, 2-methoxy-4-nitroaniline 63. 9g used as a diazo component was changed to 4-chloro-2-nitroaniline 65. 6g, and o-acetamidine methoxy used as a coupling agent component The aniline 80.3g was changed to 2'-chloroacetamidine aniline 82.0 g, and the monoazo pigment derivative A 10. 3 g The monoazo pigment derivative L 12.2g represented by the following formula was changed, and the pigment composition f 157g was obtained in the same manner as in Example 30. The pigment composition f contained the component CI Pi gment Ye 11 Omol%。 The content of O. Omol%. The content of the mono azo pigment derivative L is 5. Omol%.

Monoazo pigment derivative L

S 75 323045 201141957 Example 33 &lt;Preparation of pigment composition g&gt; Example 2 was used as a diazo component, 2-methoxy-4-indanidine 63. 9g was changed to 4-chloro-2-nitroaniline 65 6g, the o-acetamidine methoxy aniline 8 〇 3g used as a coupling agent component was changed to acetylacetanilide 68. 7g, and the monoazo pigment derivative a 1 〇 · 3g was changed to the following formula The monoazo pigment derivative Μ 8. 2 g was not obtained, and the pigment composition g HOg was obtained in the same manner as in Example 3A. Omol%。 The content of the content of the mono azo pigment derivative Μ is 5. Omol%. Sheep gas pigment derivative

OH coch3

CHCONH

OH Example 34 &lt;Preparation of pigment composition h&gt; The monoazo pigment derivative a 10.3g in Example 30 was changed to a monoazo pigment derivative N 14.1 g represented by the following formula, and the rest was In the same manner as in Example 30, a pigment group-formation h 156g was obtained. Omol%。 The content of the content of 5. Omol%. The content of the content of the azo azo pigment derivative is 5. Omol%.

Monoazo pigment derivative No 2n

76 323045 201141957 Example 35 &lt;Preparation of pigment composition i&gt; Each of the 2-methoxy-4-nitroaniline 63. 9g used as the diazo component in Example 30 was changed to dimethyl urethane terephthalate 79 5克。 By using as a coupler component, the o-acetamidine methoxyaniline 80. 3g was changed to 5-acetamethyleneamine-2-benzimidazolidinone 90. 4g, and the monoazo pigment derivative A 10.3g was changed to the monoazo pigment derivative 0 12. 2g represented by the following formula, and the pigment composition i 179g was obtained in the same manner as in Example 30. The pigment composition i contained a component of C.I. Pigment Yellow 17 5 and a monoazo pigment derivative 0, and the content of the monoazo pigment derivative 0 was 5.Omol%. Monoazo pigment derivative 0

,cooch3 coch3 N=N—CHCONH

COOCH V Γ so2nh Example 36 &lt;Preparation of pigment composition j&gt; 63. 9 g of 2-methoxy-4-nitroaniline as a diazo component was added to 500 g of water, and stirred to prepare a suspension, and then ice was added. Adjust the temperature to 5 ° C or less. Then, 105 g of 35% hydrochloric acid was added to the suspension, and the mixture was stirred for 1 hour while maintaining 5 ° C or lower. Then, an aqueous solution prepared by adding 70.0 g of sodium nitrite to 72.0 g of water was added to the suspension, and the mixture was stirred for 1 hour to carry out diazotization. To the reaction mixture was added 0. 5 g of the amine sulfonic acid to disappear, and the aqueous solution of diazonium was prepared. On the other hand, o-acetamidine methoxyacetamide 77 323045 201141957 80. 3g and 164 g of a 25% aqueous sodium hydroxide solution as a coupling agent component were added to 140 g of water, and stirred to completely dissolve. Further, an aqueous solution of 80% acetic acid 82.0 g of acetic acid and 420 g of water was prepared, and 10.3 g of a monoazo pigment derivative A was added to the aqueous solution to obtain a suspension containing the monoazo pigment derivative A. Next, the above-mentioned prepared coupling agent solution was poured into the suspension to prepare a coupling agent slurry containing the monoazo pigment derivative A. The coupler slurry containing the monoazo pigment derivative A was heated to 40 ° C, and the above-mentioned adjusted aqueous solution of diazonium was added dropwise thereto over 1 hour. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour to terminate the reaction. After the end of the reaction, the slurry was heated to 90 ° C and stirred for 1 hour, and then filtered using a Buchner funnel having a diameter of 285 mm. The filter was rinsed with 25 liters of ion-exchanged water, and then dried and pulverized to obtain a pigment composition d 152 g. Omo 1%。 The content of the monoazo pigment A is 5. Omo 1%. The content of the monoazo pigment A is 5. Omo 1%. Example 37 &lt;Preparation of Pigment Composition k&gt; The monoazo pigment derivative A in Example 36 was changed to 10.8 g of the monoazo pigment derivative B, and the rest was in the same manner as in Example 36. A pigment composition k 150 g was obtained. The content of the monoazo pigment derivative B is 5.0 mol%. The content of the monoazo pigment derivative B is 5.0 mol%. Example: &lt;Preparation of the pigment composition 1&gt; The 2-methoxy-4-nitroaniline 63. 9g used as the diazo component in Example 36 was changed to 4. 78 323045 201141957 The use of o-acetamidine aniline 80. 3g was changed to ethyl bromide 68. 7g ' and the monoazo pigment derivative a 10. 3g was changed to a single couple as shown in the following formula The nitrogen pigment derivative P 9 · 0 g was obtained in the same manner as in Example 36 to obtain a pigment composition of 1 129 g. Omol%。 The content of the mono- azo pigment derivative P is 5. Omol%.

Monoazo pigment derivative P

Example 3 9 &lt;#周制颜料组成物 m &gt; The methoxy-4 mononitramine of the diazonium component used in Example 36 was changed to 63. 9g to 5-aminoisophthalate For the dimethyl glycolate 79·&amp;, the o-acetamidine methoxy aniline 8 〇 3g used as a coupling agent component is changed to 5-acetamidine-2-benzimidazolidinone 9 〇. 4g, The monoazo pigment derivative A 10.3g was changed to the monoazo pigment derivative Q 11.Og represented by the following formula, and the pigment composition m 177g was obtained in the same manner as in Example 36. The component of the pigment composition m is c. 丨.pigment Yell〇w 120 and the monoazo pigment derivative Q, and the content of the monoazo pigment derivative Q is 5.00 mol%.

Monoazo pigment derivative Q 323045 79 201141957 h3coocv

COCH3 N=N-CHCONH

CONHiCHghNiCsHg^h3cooc Example 40 &lt;Modulating Pigment Composition n&gt;

63.9 g of 2-methoxy-4-nitroaniline used as a diazo component in Example 36 was changed to 61.2 g of 2-(trifluoromethyl)aniline, and o-acetamidine used as a coupling agent component was used. The oxime aniline 80. 3g was changed to 5-acetamidine-2-benzene. 9 g of the fluorene ketone was changed, and the monoazo pigment derivative A 10.3 g was changed to the monoazo pigment derivative R 12.8 g represented by the following formula, and the others were obtained in the same manner as in Example 36. Pigment composition n 161g. Omol 1%。 The content of the mono azo pigment derivative R is 5. Omo 1%. The content of the mono azo pigment derivative R is 5. Omo 1%. Monoazo pigment derivative R

OH Example 41 &lt;Preparation of the pigment composition 〇&gt; Each of the 2-methoxy-4-nitroaniline 63. 9g used as the diazo component in Example 36 was changed to o-methoxyaniline 46. 8g, 4克。 The monoazo dye derivative A 10. The acetophenone oxime ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone 3 g was changed to a single azo pigment derivative S 9. 8 g represented by the following formula, and the pigment composition 〇145 g was obtained in the same manner as in Example 36. Pigment 80 323045 201141957

The component contained in the composition 0 was C.I. Pigment Yellow 194 and the monoazo pigment derivative S, and the content of the monoazo pigment derivative S was 5.0 mol%. Monoazo pigment derivative S OCH,

COCH3 n=:n—chconh

Example 42 &lt;Preparation of Pigment Composition p&gt; 67.3 g of 2-methoxy-4-nitroaniline as a diazo component was added to 500 g of water and stirred to prepare a suspension, and ice was added thereto to adjust the temperature to 5 Below C. Then, 105 g of 35% hydrochloric acid was added to the suspension, and the mixture was stirred for 1 hour while maintaining 5 C or less. Then, an aqueous solution prepared by adding sodium nitrite 28·〇g to 72. Og of water was added to the suspension, and the mixture was poured for 1 hour to carry out diazotization. To the reaction mixture, an amine sulfonate 5 g was added to make nitrous acid disappear, and then water was added to adjust the amount of the solution to 1000 g, and an aqueous solution of diazonium was prepared. On the other hand, o-acetamidine methoxybenzamine 8 〇.3g as a coupling agent component and 164 g of a 25% aqueous sodium hydroxide solution and 164 g of a 25% aqueous sodium hydroxide solution were added to 14 〇g of water. The mixture was stirred to completely dissolve, and then water was added to adjust the liquid 3: to 4 〇〇g to prepare an aqueous solution of the coupling agent. 2克 uniformly mixed with water 365g and 80% acetic acid 64. Og, 25% sodium hydroxide water / liquid mixture to prepare an aqueous solution. The aqueous solution was heated to 4 ° C while maintaining the temperature, and the aqueous solution of the diazonium dihydroxide and the aqueous coupler solution were added dropwise over 1 hour, respectively, and the pH of the reaction vessel was ensured to be 6.0 323045 201141957 or less. After completion of the dropwise addition, the mixture was stirred at 40 ° C for 1 hour to terminate the reaction. After the end of the anti-deer, the liquid was heated to 90 C and allowed to stand for 1 hour, and then filtered using a 285 mm Buchner funnel. The filter residue was washed with ion-exchanged water &amp; liters, and then dried and pulverized to obtain a pigment composition p 151 g. Omo1%。 The content of the mono- azo pigment derivative A is 5. Omo 1%. The content of the mono- azo pigment derivative A is 5. Omo 1%. Example 43 &lt;Preparation of Pigment Composition q&gt; The acetamidine anilide compound a 6·8g used in Example 42 was changed to acetamidine anilide compound B 7.4 g, and the rest was in the same manner as in Example 42 The pigment composition q 152g was obtained. The composition of the pigment composition q is a monoazo pigment A (C.I. Pigment Yellow 74) and a monoazo pigment derivative B, and the content of the monoazo pigment derivative b is 5. Om〇1〇/〇. Example 4 &lt;Preparation of the pigment composition r&gt; The 2-methoxy-4-nitroaniline 67. 3g used as the diazo component in Example 42 was changed to 4-chloro-2-nitroaniline 69. 0g, and 6 g of o-acetamethylene methoxyaniline 8Q. 3g used as a coupling agent component was changed to 2,4,-dimethylethyl oxime anilide 79. 6 g, and the pigment was obtained in the same manner as in Example 42 except for the pigment. Composition r 153g. The content of the pigment composition r is C.I. Pigment Yellow 2 and the monoazo pigment derivative represented by the following formula: The content of the 单'monoazo pigment derivative T is 5.0 mol%.

Monoazo pigment derivative T 82 323045 201141957

Conh(ch2)3n(c2h5)2 Example 45 &lt;Preparation of pigment composition s&gt; The acetamidine anilide compound A 6. 8g in Example 42 was changed to the acetophenone anilide compound U shown by the following formula 6. g, the rest was obtained in the same manner as in Example 42 to obtain a pigment composition s 152 g. 5% ◊ 含量 含量 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ethyl anilide compound U C〇CH3 CH2CONH&lt; S02NH(CH2)3M(CH3)2 monoazo pigment derivative u o2n

COCH,

So2nh(ch2)3n(ch3&gt;2 Example 46 &lt;Preparation of pigment composition t&gt; 6-glycol-4-nitroaniline used as a diazo component in Example 42 67. 3g was changed to 4-chloro-2 5克的乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙乙'''''''' The indole anilide compound A 6. 8g was changed to the acetamidine anilide compound V 8. 8g represented by the following formula, and the pigment composition t 162g was obtained in the same manner as in Example 42. Pigment 83 323045 201141957 Composition Omol%。 The content of the mono azo pigment derivative V is 5. Omol%.

Acetylacetate compound V

Monoazo pigment derivative V

</ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> The ethyl acetanilide compound A 6.8 g was changed to the acetonitrile anilide compound W 10.7 g represented by the following formula, and the pigment composition u 149 g was obtained in the same manner as in Example 42. Omol 1%。 The content of the mono azo pigment derivative W is 5. Omo 1%. The content of the mono azo pigment derivative W is 5. Omo 1%.

Ethyl acetonitrile compound W 84 323045 201141957

Example 48 &lt;Preparation of pigment composition v &gt; 63.9 g of 2-nonyloxyaniline as a diazo component was added to 500 g of water, stirred to prepare a suspension, and ice was added thereto to adjust the temperature to 5 C or less. Then, 1 〇 5 g of 35% hydrochloric acid was added to the suspension, and while maintaining at 5 ° C or lower, 1 (four) was stirred. An aqueous solution prepared by adding sodium nitrite 28 〇g to 72. Og of water was added to the suspension (iv), and the mixture was mixed for 1 hour to carry out diazotization. An amine bismuth hydride was added to the reaction mixture. 5 g of nitrous acid was eliminated, and then water was added to adjust the amount of the solution to 1 〇〇〇g, and an aqueous solution of diazonium was prepared. On the other hand, 80 g of o-acetamidine methoxyaniline as a coupling agent component and 164 g of a 25% aqueous sodium hydroxide solution were added to 14 μg of water, and stirred up to completely dissolve 'then adding water to the amount of liquid. The solution was adjusted to 4 GGg to prepare an aqueous solution of the coupling agent. 6. In the reaction vessel, 365 g of water and 8 〇% acetic acid 64. 〇g, 25% sodium hydroxide water-cooled liquid 71·2 g were uniformly mixed to prepare an aqueous solution. Then, a monoazo pigment derivative A 1Q.2g was added to the aqueous solution and uniformly mixed to form a suspension. 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. After the completion of the dropwise addition, the mixture was stirred at 4 ° C for 1 hour to terminate the reaction. After the end of the reaction, the slurry was heated to 9 ° C and spoiled for 1 hour, and then filtered using a 285 mm Buchner funnel. The filter residue was washed with 25 liters of ion-exchanged water, and then dried and pulverized to obtain a pigment composition v 152 g. Omo1%。 The content of the composition of the composition of the composition of the composition of the mono-azo pigment A (C. I. Pigment Yellow 74) and the monoazo pigment derivative A, the content of the early gas pigment bamboo organism A is 5. Omo 1%. Example 49 &lt;Preparation of pigment composition w&gt; The monoazo pigment derivative A 1〇. 2g used in Example 48 was changed to a monoazo pigment derivative B l〇.8g, and the rest was the same as in Example 48. In the manner, a pigment composition w 152 g was obtained. The content of the mono-azo pigment A (C. I. Pigment Yellow 74) and the monoazo pigment derivative B' monoazo pigment derivative b is 5. 〇m〇i%. Example 50 &lt;Preparation of Pigment Composition χ&gt; 2-methoxy-4-nitroaniline 63·9g as a diazo component was added to 5 〇〇g of water, and stirred to prepare a suspension, and then ice was added. The temperature is adjusted to 5. € below. Then, 35% of 55% hydrochloric acid was added to the suspension, and the mixture was maintained for 5 Torr or less for 1 hour. Then, an aqueous solution in which sodium nitrite 28. 〇g was dissolved in 72. Og of water was added to the suspension, and the mixture was stirred for 1 hour, whereby diazotization was carried out. Adding an amine hydrazine to the reaction mixture. 5 Avoid nitrous acid disappearing, and prepare an aqueous solution of diazo rust. On the other hand, 164 g of the phthalocyanine 323045 86 201141957 8〇·3g and 25% of the aqueous sodium oxide solution as a coupling agent were added to 14 〇g of water to completely dissolve. The aqueous solution was poured into an aqueous solution mixed with 80% acetic acid 82 〇g and water 420 g to prepare a coupling agent slurry. Oh,

The prepared coupling agent slurry was heated to 4 (rc, in which an aqueous solution of diazo rust was added dropwise over 1 hour. After the addition was completed, a single pigment and a living organism A 10.2 § was added to the liquid, and the mixture was directly mixed at the temperature for 1 hour. Then, the water is heated to 9 (rc and H is mixed, and then filtered) by using a Buchner funnel of 285. The filter is rinsed with 25 liters of ion-exchanged water, then dried and pulverized. The pigment composition χ The pigment composition Χ is composed of a single opaque pigment A (CIpigment Yellow 74) and a monoazo pigment derivative A, and the content of monoazo pigment is 5. 〇mol%. A. Example 51 &lt;Preparation of pigment composition y&gt; π The monoazo pigment derivative A 1〇. 2g used in Example 50 was changed to monoazo pigment derivative B 10.8 g, and the rest was the same as in Example 5 The formula = y l5Qg is obtained. The pigment composition contains a single azo pigment A (C. Uigmenl: Yellow 74) and a monoazo pigment He B, a monoazo pigment derivative. The content of β is 5. 〇mol%. &lt;Evaluation of early azo pigments and pigment compositions> Needle The specific azo pigments and pigment compositions prepared in Production Examples 1 to 6 and Examples 丨 to 51 were measured for specific electrical conductivity and metal content of the average primary particle diameter and extracted water. The results are summarized in Table 3. Measured by 10,000 Å (average primary particle size) 323045 87 201141957 The average-minor particle size is determined by the particle size of the pigment or pigment composition photographed by the sweeping tweezers microscope. A conductive double-sided tape is attached to a pigment or a pigment composition, and platinum is vapor-deposited on the surface of the sample by means of an organic ore to be used as a sample. A scanning electron microscope (JSM_67, manufactured by JEOL DATUM Co., Ltd.) is used. A fr-type scanning electron microscope) is used to photograph particles, and the individual maximum diameters of 100 primary particles of the pigment or pigment composition captured in the same field of view are measured. The average value of these is calculated, and the value is averaged. &lt;Specific Conductivity of Extracted Water&gt; The monoazo pigment or pigment composition 5. 〇g was wetted with ethanol of 10.0 g, and ion-exchanged water of 90·Og was added to make a slurry. The slurry was heated while being stirred by a magnetic stirrer, and after boiling, it was mixed for 5 minutes. After the completion of the mixing, the mixture was cooled to room temperature, and then ion-exchanged water was added to make the total amount of the slurry 105. Og. The slurry was filtered by five kinds of C filter papers specified in jIS p 3801. The filtrate receiving container was washed with filtrate, and then the filtrate was filled, and the ratio was measured by a conductivity meter (manufactured by Toa DKK Co., Ltd., CM-40V). Conductivity. — (Metal content) About 2 g of a monoazo pigment or pigment composition was added to 8 ml of nitric acid, and the temperature was recorded in Table 1 by a microwave sample pretreatment apparatus ("ETH0S1" manufactured by Milestone General Co., Ltd.). Temperature program). 88 323045 201141957 [Table 1] STEP time (minutes) Maximum output (W) Internal temperature rc ) T1 Temperature (°C) Τ 2 120 ion 1 2 1000 70 2 1 0 50 3 15 1000 230 〜一 — 120 4 10 —- --:--1 1000 ___120 After cooling the treatment solution to room temperature, 2 ml of nitric acid was added, and the treatment was carried out according to the temperature schedule described in Table 2. [Table 2]

The treatment liquid was filtered using five kinds of C filter papers prescribed in JIS P 3801, and the filtrate was adjusted to a volume in a 50 ml volumetric flask to prepare a measurement sample. The measurement sample was measured by a multiplex ICP emission spectroscopic analyzer (Model 720-ES, manufactured by Varian Technologies Japan Ltd.) to quantify each metal element. s 89 323045 Composition specific conductivity (/iS/cm) Golden eyebrow containing Dong (ppm) Single material ffitUft derivative Average 1 seed (CIPig. Y) Containing Dong (molX) Seed cheek containing Dong (molX) (nm) Ca Mg Fe meter manufacturing example 1 筚偁lUfi material A 74 100 125 60 55 28 77 160 «Example 2 Single nipple material B 1 100 120 71 32 13 56 101 Production example 3 Single nipple c 9 100 118 80 57 10 66 133 Production example 4 Single 偁fL pigment D 73 100 113 59 46 22 38 106 Production example 5 Single 偁IUR material E 105 100 115 73 50 12 58 120 Example 6 偁 偁 F F 213 100 130 82 63 24 65 152 Example 1 Pigment composition A 74 95 A 5 122 85 55 22 52 129 Example 2 Pigment composition B 74 95 B 5 115 92 40 12 64 116 Remarks 3 Pigments &amp; Compound C 1 95 C 5 122 86 50 14 68 '32 Example 4 Dip composition D 9 95 D 5 130 77 52 14 49 1 115 Example 5 Pigment composition E 73 95 E 5 Π 8 88 39 21 57 Η; Example 6 Composition of the material F 105 95 F 5 131 go 40 14 55 109 Example 7 Pigment red product G 213 95 G 5 125 78 55 10 41 Example 8 Pigment composition Η 74 95 A 5 70 76 44 12 32 «« Poor Practice 9 Pigment composition 1 74 95 A 5 68 240 168 157 88 Example 10 Rhodium composition J 74 95 B 5 71 81 63 12 27 102 Example 11 Pigment composition Κ 74 95 B 5 72 310 180 95 160 435 Appreciation Example 12 Composition of the material L 74 95 A 5 80 88 49 12 39 100 Example 13 Pigment Μ 74 99.95 A 0.05 128 94 50 13 46 109_ Poor Example 14 Pigment composition Ν 74 99.5 A 0.5 115 54 33 13 45 91 Example 15 Pigment composition 0 74 85 A 15 53 80 51 20 37 108 Example 16 Pigment composition Ρ 74 70 A 30 45 88 39 11 38 88 Example 颜料 Pigment composition Q 74 50 A 50 21 94 45 21 41 107 Example 18 Pigment composition R 74 95 B 5 83 69 64 24 48 136 Example 19 Pigment composition S 74 99.95 B 0.05 130 93 48 15 45 108 Example 20 Pigment composition Τ 74 99.5 B 0.5 120 94 49 20 42 Example 21 Pigment composition ϋ 74 85 B 15 42 70 51 19 58 128 Example 22 Pigment composition V 74 70 B 30 29 83 60 10 44 114 Example 23 Pigment composition ff 74 50 B 50 19 71 38 15 55 108 Example 24 Pigment composition X 49 95 H 5 75 82 50 12 47 09 Example 25 Pigment composition Y 97 95 I 5 84 92 37 28 42 107 Example 26 Pigment composition Z 111 95 J 5 92 88 54 11 46 111 Example 27 Pigment composition a 167 95 K 5 84 97 51 16 24 91 Example 28 Pigment composition b 74 95 A 5 87 42 24 11 37 72 Example 29 Pigment composition C 74 95 B 5 74 89 22 22 39 83 Example 30 Pigment composition d 74 95 A 5 98 84 70 25 57 152 Example 31 Pigment composition e 74 95 B 5 105 84 53 20 40 113 Example 32 Pigment composition f 3 95 L 5 89 90 53 12 50 115 Appreciation Example 33 Pigment composition g 6 95 M 5 110 83 38 11 48 97 Example 34 Pigment Composition h 74 95 N 5 102 75 33 15 47 95 Example 35 Pigment composition im 95 0 5 97 93 34 24 51 109 Example 36 Pigment composition j 74 95 A 5 100 73 39 13 54 106 Example 37枓 Composition k 74 95 B 5 88 92 52 23 44 119 Example 38 Pigment composition 1 4 95 P 5 90 72 54 14 48 116 Example 39 Pigment composition m 120 95 Q 5 97 78 40 14 28 82 Example 40 Pigment Composition π 154 95 R 5 92 84 34 21 】 9 74 Example 41 Pigment Composition 0 194 95 S 5 104 91 34 13 57 104 Example 42 Pigment Composition p 74 95 A 5 87 76 46 23 50 119 Example 43 Pigment composition q 74 95 B 5 76 78 54 18 40 112 Example 44 Pigment composition Γ 2 95 T 5 92 86 61 12 33 106 Example 45 Pigment composition S 74 95 l; 5 89 69 51 31 29 111 Example 46 Pigment composition t 98 95 V 5 79 89 53 13 43 109 Example 47 Pigment composition u 203 -95 ff 5 94 88 47 30 48 125 Implementation Example 48 Pigment Composition V 74 95 A 5 99 93 29 12 54 95 Example 49 Pigment Composition w 74 95 δ 5 105 92 46 22 51 119 Example 50 Pigment Composition X 74 95 A 5 114 71 62 12 39 113 Example 51 Pigment composition y 74 95 B 5 118 90 50 14 47 111 201141957 [Table 3] 90 323045 201141957 &lt;Preparation of Pigment Dispersion&gt; (Preparation of Oily Pigment Dispersion) Examples 52 to 76 and Comparative Example 1 To 3 pigment compositions or monoazo pigments lOOOO'Disperbyk 130

(BYK Chemie, pigment dispersant) 325g, JONCRYL 586 (BASF

25 g of styrene-acrylic resin, 925 g of ethylene glycol monobutyl ether acetate, and 905 g of ethylene glycol monobutyl ether acetate were mixed and stirred until uniform by a high speed mixer. Then, it was dispersed by a horizontal wet disperser (DYn〇-MILL TYPE KDL-PIL0T) for 2 hours, and then ethylene glycol monobutyl ether acetate 2500 g was added and redispersed for 1 hour to obtain an oily pigment dispersion a to z. The pigment composition or the monoazo pigment used in each of the oil pigment dispersions of a to b ° is shown in Table 4. Comparative Example 4 (Preparation of oily pigment dispersion c) Change of pigment composition or monoazo pigment to Hansa Brilliant

Ye 1 low 5GX (C. I. Pigment Ye 1 low 74, manufactured by Clarion Co., Ltd.), and the oily pigment dispersion c was obtained in the same manner as in Examples 52 to 76 and Comparative Examples 1 to 3. (Preparation of aqueous pigment dispersion) Examples 77 to 102 and Comparative Examples 5 to 7 Pigment composition or monoazo pigment 1000 g, JONCRYL HPD-96J (BASF Japan, styrene-acrylic resin, active ingredient 34) 〇%) 735g'SURFYNOL 104E (made by Air·Products and Chemicals Co., Ltd., antifoaming agent, active ingredient 50%) 50g, Levanax BX-150 (preservative manufactured by Changrong Chemical Co., Ltd.) 50g, propylene glycol 250g, Ion 91 323045 201141957 415 g of exchanged water was mixed and stirred until uniform by a high-speed mixer. Next, it was dispersed by a horizontal wet disperser (DYNO-MILL TYPE KDL-PIL0T) for 2 hours' and then ion-exchanged water was added. g was further dispersed for 1 hour to obtain aqueous pigment dispersions A to Z and a to c. The pigment composition or monoazo pigment used in each aqueous pigment dispersion is summarized in Table 5. Comparative Example 8 (Preparation of aqueous pigment dispersion d) Change of pigment composition or monoazo pigment to Hansa Brilliant

Yellow 5GX (manufactured by Clariant Co., Ltd., C. I. Pigment Yellow 74), the remainder was obtained in the same manner as in Examples 77 to 102 and Comparative Examples 5 to 7, to obtain an aqueous pigment dispersion d. &lt;Evaluation of Pigment Dispersion&gt; The dispersion of the pigment, the particle size, the viscosity, the crystal stability, and the storage stability were evaluated by the following methods. The results are shown in Table 4 and Table 5 ° (Dispersed particle size) The dispersed particle size was evaluated by D50 measured by Microtrac UPA-150 (manufactured by Nikkiso Co., Ltd.). (Viscosity) The viscosity was evaluated by a value of 6 rpm measured by a B-type viscometer VISCOMETER (manufactured by Toki Sangyo Co., Ltd.). (Crystal Stability) A photograph of particles of a pigment or a pigment composition in a pigment dispersion was taken by a transmission electron microscope, and this was taken as an index of crystal stability. The pigment dispersion was dropped on a sieve with a support film, and dried as a sample of 92 323045 201141957', and then the particles were photographed by a penetrating electron microscope (manufactured by Hitachi Co., Ltd., μ ga sub microscope) for the same 塀HHHI of the pigment or pigment composition photographed by the native 电视4Αα main tooth of your soil TV field f: the recording of the ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( The pigment dispersion was sealed in a screw cap bottle, and stored in the 7th generation for 4 weeks, and the same measurement was carried out. The crystal stability was evaluated by the change of the average-secondary particle size before and after storage. The rate of change of the average primary particle diameter before and after storage was 0 to 15%, and it was judged that 〇' exceeded 15% and was 30% or less, and it was judged as △, and when it exceeded 30%, it was judged as X. (Storage stability) The pigment dispersion was sealed in a screw cap bottle, and stored at 70 ° C for 4 weeks, and then the dispersed particle diameter and viscosity were measured. The storage stability was evaluated by the change in the dispersed particle diameter and viscosity before and after storage, and the presence or absence of the precipitate after storage. s. 93 323045 201141957 [Table 4] Pigment composition DsoCnm) Dot (mPa · s) Crystallization stability after initial storage after initial storage of precipitate or mono-anthracene pigment Example 52 Oil-based pigment dispersion A Pigment composition A 174 168 7.3 6.9 〇 No Example 53 Oily pigment dispersion asB Pigment composition D 163 176 9.3 9.7 〇 No Example 54 Oily pigment dispersion C Pigment composition F 164 158 Ϊ 0.1 11.2 〇 No Example 55 Oily pigment dispersion Body D Pigment Composition J 185 171 9.3 8.0 〇 No Example 56 Oily Pigment Dispersion E Pigment Composition K 131 134 12.4 12. 1 〇 No Example 57 Oily Pigment Dispersion 艏F Pigment Composition L 129 125 11.1 12. 1 〇 none Example 58 Oily Pigment Dispersion G Pigment Composition Μ 213 225 32.8 49.9 △ No Example 59 Oily Pigment Dispersion Η Pigment Composition Ν 116 113 18.8 17.9 〇 No Example 60 Oily Pigment Dispersion 逋 1 Pigment Composition 0 119 118 10.3 10.9 〇No Example 61 Oily Pigment Dispersion J Pigment Composition Ρ 128 140 8.4 9.4 〇 No Example 62 Oily Pigment Dispersion Κ Pigment Composition Material Q 152 134 45.6 58.7 〇No Example 63 Oily Pigment Dispersion L Pigment Composition X 123 125 10.7 9.7 〇No Example 64 Oily Pigment Dispersion Μ Pigment Composition 119 119 117 11.6 10.2 〇No Example 65 Oily Pigment Dispersion Body Ν Pigment composition b 128 138 9.0 10. 1 〇 No Example 66 Oily pigment dispersion 0 Pigment composition e 113 109 12.2 11.0 〇 No Example 67 Oily pigment dispersion Ρ Pigment composition g 141 143 11.8 12.7 〇 No Example 68 Oil-based pigment dispersion Q Pigment composition i 153 138 11.7 10.5 〇 No Example 69 Oil-based pigment dispersion R Pigment composition j 141 134 16.4 15.8 〇 No Example 70 Oil-based pigment dispersion S Pigment composition 1 136 129 13.6 14.6 〇No Example 71 Oily pigment dispersion Τ Pigment composition η 145 122 12.0 12.7 〇No Example 72 Oily pigment dispersion U Pigment composition ρ 137 123 12.1 11.5 〇No Example 73 Oily pigment dispersion V Pigment composition S 119 143 11.8 11.6 〇No Example 74 Oily pigment dispersion tf Pigment composition U 153 144 10.2 11.0 〇No example 75 Pigment dispersion X Pigment composition V 139 140 17.1 18.6 〇 No Example 76 Oily pigment dispersion Y Pigment composition V 129 131 13.6 14. t 〇 No comparative example 1 Oily pigment dispersion Z Monoazo pigment A 240 551 63.7 761 X Comparative Example 2 Oily pigment dispersion a Monofluorene pigment C 225 690 80.5 594 X Comparative Example 3 Oily pigment dispersion b Monoazo pigment E 256 574 74.1 630 X Comparative Example 4 Oily pigment dispersion C Hansa Brilliant Yellow 5GX 378 835 59.2 638 X has 94 323045 201141957 As shown in Table 4, the oily pigment dispersion prepared by using the pigment composition obtained by the present invention has a lower viscosity and dispersed particles than others. The diameter is small and shows good dispersion. These oily pigment dispersions have good storage stability and crystal stability. s 95 323045 201141957 [Table 5] Pigment composition Ds 〇 (nm) Viscosity (mPa · s) Shen two: Crystal stability after initial preservation after initial storage of material or monoazo pigment Example 77 Aqueous pigment dispersion A Pigment Composition B 160 149 7.9 9.5 〇 No Example 78 Aqueous Pigment Dispersion Zhao B Pigment Composition C 152 137 10.7 9.3 〇 No Example 79 Aqueous Pigment Dispersion C Pigment Composition E 154 140 8.4 9.3 〇 No Example 80 Water-based Pigment Dispersion D Pigment Composition G 166 153 10.4 8.5 〇 No Example 81 Water-based pigment dispersion E Pigment composition Η 123 124 10.4 10.7 〇 No Example 82 Aqueous pigment dispersion «F 枓 composition I 120 115 11.7 11.3 〇 none Example 83 Aqueous Pigment Dispersion G Pigment Composition R 125 106 12.6 8.6 〇 No Example 84 Aqueous Pigment Dispersion 颜料 Pigment Composition S 207 192 29.8 44.9 △ No Example 85 Aqueous Pigment Dispersion 艎 I Pigment Composition Τ 109 108 8.7 7.3 〇No Example 86 Aqueous pigment dispersion 艏j 枓 composition U 123 106 12.7 11.9 〇No example 87 Aqueous pigment dispersion Κ Pigment composition V 116 96 9.8 10.9 〇 No Example 88 Aqueous Pigment Dispersion L Pigment Composition ff 141 130 39.7 53.3 △ No Example 89 Aqueous Pigment Dispersion Μ Pigment Composition Y 115 114 12.3 11.2 〇 No Example 90 Aqueous Pigment Dispersion颜料 Pigment composition a 121 120 12.8 12.4 〇 No Example 91 Aqueous pigment dispersion 0 枓 Composition C 104 85 11.6 11.5 〇 No Example 92 Aqueous pigment dispersion 枓 枓 composition d 129 123 7.4 8.5 〇 No implementation Example 93 Aqueous Pigment Dispersion Q Pigment Composition f 141 127 8.4 9.8 〇 No Example 94 Aqueous Pigment Dispersion R Pigment Composition h 136 138 11.6 11.3 〇No Example 95 Aqueous Pigment Dispersion S 枓 枓 Composition k 117 102 11.4 10.4 〇No Example 96 Aqueous Pigment Dispersion Τ Pigment Composition m 140 142 10.9 10.0 〇No Example 97 Aqueous Pigment Dispersion U Pigment Composition 〇125 116 10.1 9.4 〇No Example 98 Aqueous Pigment Dispersion V Pigment Composition Material q 110 110 9.9 9.3 〇 No Example 99 Aqueous pigment dispersion ff Pigment composition 147 147 140 9.6 10*4 〇 No Example 100 Water-based pigment Dispersion X Pigment Composition t 120 116 10,2 11.4 〇No Example 101 Aqueous Pigment Dispersion Y Pigment Composition w 119 120 8.6 9.4 〇 No Example 102 Aqueous Pigment Dispersion Z Pigment Composition X 144 146 9.8 9.7 〇 No Comparative Example 5 Aqueous pigment dispersion a Monofluorene pigment B 247 481 41.8 526 X Comparative Example 6 Aqueous pigment dispersion b Monoazo pigment D 251 510 70.0 874 X Comparative Example 7 Aqueous pigment dispersion C Monofluorene nitrogen Pigment F 283 637 86.4 579 X Comparative Example 8 Aqueous Pigment Dispersion d Hansa Brilliant Yellow 5GX 341 754 76.8 794 X Available 96 323045 201141957 As shown in Table 5, an aqueous preparation prepared by using the pigment composition obtained by the present invention The dispersion has a lower sister content and a smaller dispersion particle size than others, showing good dispersibility. These aqueous pigment dispersions are excellent in storage stability and crystal stability. The oily pigment dispersion prepared in Examples 57 to 76 and Comparative Examples 1 to 4 was 25. 0 g. , propylene glycol monomethyl ether acetate 1 〇〇 g, ethylene glycol monobutyl ether acetate 55.0 g of diethylene glycol monoethyl ether acetate 1 〇〇 g was mixed and stirred for 1 hour, and then with a pore size of 1.0 Am PTFE filter membrane was filtered to obtain oily inkjet inks A to Z and a to c. (Improved aqueous inkjet ink) Examples 128 to 153 and Comparative Examples 13 to 16 The aqueous pigment dispersions prepared in Examples 77 to 102 and Comparative Examples 5 to 8 were 5.0 g, acrylic resin emulsion w-215 (Japan 5克), the solid content of 30%) 1.5g, ethylene glycol 15.0g, ion exchange water 68. 5g were mixed and stirred for 1 hour, and then filtered with a PTFE membrane with a pore size of 1. Aqueous inkjet inks a to Z and a to d were obtained. &lt;Evaluation of inkjet ink&gt; (Evaluation of oil-based inkjet ink) The discharge property of the ink jet printer of the oil-based inkjet ink and the coloring power of the obtained print were evaluated. The results are summarized in Table 6. 97 323045 201141957 (Spit-out) In the evaluation of the spit-out, the oil-based inkjet ink is filled in the ink cartridge of the inkjet printer IP_6500 (made by Seiko Instruments Inc.) and printed on Glossy polyvinyl chloride sheet MD5 (manufactured by Metamark). The presence or absence of dead spots (unprinted parts) in the printed matter was visually observed and used as an indicator of spitting. If the nozzle of the printer head of the printer having a dead pixel is less than 1% of the total nozzle, it is judged to be 〇, and if it is 1% or more and less than 5%, it is judged that Δ' exceeds 5% and it is judged as X. (Coloring power) In the evaluation of the coloring power, the reflection density of the portion where no bad point occurred was measured for each of the prints by a reflection densitometer D19C (manufactured by Gretag Machbeth Co., Ltd.). The oil-based inkjet ink c prepared in Comparative Example 12 was used as a reference. The reflection concentration ratio was greater than 9〇% and the amount was less than 1〇5%, and it was judged as Δ, and the reflection concentration ratio was 105% or more. Those who do not reach 90% are judged as X. (Evaluation of aqueous inkjet ink) The discharge property of the printer of the aqueous inkjet ink and the coloring power of the obtained print were evaluated. The results are summarized in Table 7. (Spit-out property) In the evaluation of the discharge property, the aqueous inkjet ink was filled in the ink cartridge of the inkjet printer HG-5130 (manufactured by Seiko Epson Co., Ltd.), and printed on the shell surface gold card image. Paper (made by Canon Inc.). Visually observe the presence or absence of dead spots (unprinted parts) in the printed matter and use them as indicators of spit out. The nozzle of the printer head that has a bad point has not reached the total spray 98 323045 201141957 One of the mouths is judged to be 〇, 1% or more and less than 5% is judged as △, and more than 5% is judged as X. (Coloring power) In the evaluation of the coloring power, the reflection density of the portion where no bad point occurred was measured for each of the prints by a reflection densitometer D19C (manufactured by Gretag Machbeth Co., Ltd.). With reference to the aqueous inkjet ink d prepared in Comparative Example 16, the reflection density ratio was greater than 95% and less than 105% was judged as Δ, and when the reflection density ratio was 105% or more, it was judged as 〇, and the reflection density ratio was less than 95. % is judged as X. 99 323045 201141957 [Table 6] Oily Pigment Dispersion Discharge Coloring Force Example 103 Oily Inkjet Ink A Oily Pigment Dispersion A 〇〇 Example 104 Oily 嗔Ink Printing. 5 B Oily Pigment Dispersion B 〇〇 Example 105 Oil-based inkjet ink C Oil-based pigment dispersion C 〇〇 Example 106 Oil-based inkjet ink D Oil-based pigment dispersion D 〇〇 Example 107 Oil-based inkjet printing ink E Oil-based pigment dispersion E Δ 〇 Example 108 Oil-based inkjet ink F Oily pigment dispersion F 〇〇 Example 109 Oil-based inkjet ink G Oil-based pigment dispersion G Δ Δ Example 110 Oil-based inkjet ink Η Oil-based pigment dispersion Η Example 111 Oil-based Inkjet Ink I Oily Pigment Dispersion I 〇〇 Example 112 Oily Inkjet Ink J Oily Pigment Dispersion J 〇〇 Example 113 Oily Inkjet Ink Κ Oily Pigment Dispersion Κ 〇Δ Example 114 Oily Inkjet Ink L Oily Pigment Dispersion L 〇〇 Example 115 Oily Inkjet Ink Μ Oily Pigment Dispersion Μ Example 116 Oily Inkjet Ink Ν Oily Pigment Dispersion Ν 〇〇 117 Oily Inkjet Ink 0 Oily Pigment Dispersion 0 〇〇 Example 118 Oily Inkjet Ink Ρ Oily Pigment Dispersion Ρ Example 119 Oily Inkjet Ink Q Oily Pigment Dispersion Q 〇〇 Example 120 Oiliness Inkjet Ink R Oily Pigment Dispersion R 〇〇 Example 121 Oily Inkjet Ink S Oily Pigment Dispersion S 〇〇 Example 122 Oily Inkjet Ink Τ Oily Pigment Dispersion Τ Example 123 Oily Inkjet Ink U Oily Pigment Dispersion U 〇〇. Example 124 Oily Inkjet Ink V Oily Pigment Dispersion V 〇〇 Example 125 Oily Inkjet Ink W Oily Pigment Dispersion W 〇〇 Example 126 Oily Inkjet Printing Ink X Oily Pigment Dispersion X 〇〇 Example 127 Oily Inkjet Ink Υ Oily Pigment Dispersion Υ 〇〇 Comparative Example 9 Oily Inkjet Ink Ζ Oily Pigment Dispersion Ζ X Δ Comparative Example 10 Oily Inkjet Ink Oily Pigment Dispersion a XX Comparative Example 11 Oily Ink Printing Ink b Oily Pigment Dispersion b XX Comparative Example 12 Oily Inkjet Ink C Oily Pigment Dispersion CX Δ 100 323045 201141957 As shown in Table 6 The oil-based inkjet ink prepared by using the pigment composition obtained by the present invention is excellent in spouting property and coloring power as compared with others. 101 323045 201141957 [Table 7] Aqueous Pigment Dispersion Discharge Coloring Force Using Example 128 Aqueous Inkjet Ink A Aqueous Pigment Dispersion A 〇〇 Example 129 Aqueous Inkjet Ink B Aqueous Pigment Dispersion B 〇〇 ' Example 130 Aqueous Inkjet Ink C Aqueous Pigment Dispersion C 〇〇 Example 131 Aqueous Inkjet Ink D Aqueous Pigment Dispersion D Example 132 Aqueous Inkjet Ink E Aqueous Pigment Dispersion E 〇〇Example 133 Waterborne Inkjet Ink F Aqueous Pigment Dispersion F Δ Δ Example 134 Aqueous Inkjet Ink G Aqueous Pigment Dispersion G 〇〇 Example 135 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Η Δ Δ Example 136 Waterborne Inkjet Ink I Aqueous Pigment Dispersion I 〇〇 Example 137 Aqueous Inkjet Ink J Aqueous Pigment Dispersion J 〇〇 Example 138 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Κ Example 139 Aqueous Inkjet Ink L Aqueous Pigment Dispersion L Δ Δ Example 140 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Μ Example 141 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Ν 〇〇 Example 142 Aqueous inkjet ink 0 Aqueous pigment dispersion 0 〇〇 Example 143 Aqueous inkjet ink cartridge Aqueous pigment dispersion Ρ Example 144 Aqueous inkjet ink Q Aqueous pigment dispersion Zhao Q 〇〇 Example 145 Aqueous Inkjet Ink R Aqueous Pigment Dispersion R 〇〇 Example 146 Aqueous Inkjet Ink S Aqueous Pigment Dispersion S 〇〇 Example 147 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Τ Example 148 Aqueous Spray Inkjet ink U Aqueous pigment dispersion U 〇 〇 Example 149 Aqueous inkjet ink V Aqueous pigment dispersion V 〇〇 Example 150 Aqueous inkjet ink W Aqueous pigment dispersion ff 〇〇 Example 151 Water-based inkjet Ink X Aqueous Pigment Dispersion X 〇〇 Example 152 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Y 〇〇 Example 153 Aqueous Inkjet Inkjet Aqueous Pigment Dispersion Z 〇〇 Comparative Example 13 Aqueous Inkjet Ink a Aqueous pigment dispersion a XX Comparative Example 14 Aqueous inkjet ink b Aqueous pigment dispersion b XX Comparative Example 15 Aqueous inkjet ink c Aqueous pigment dispersion CXX Comparative Example 16 Aqueous inkjet ink d Water-based Pigment Dispersion d X Δ 102 323045 201141957 As shown in the results of Table 7, the aqueous inkjet ink prepared by using the pigment composition obtained by the present invention is excellent in spit and coloring power as compared with others. . Next, the colored resin composition and the toner of the present invention will be described in detail by way of examples, but the present invention is not limited thereto. Further, the adhesive resins used in Examples 154 to 175 and Comparative Examples 17 to 20 used the following thermoplastic polyester resins. &lt;Bonding Resin&gt; Thermoplastic Polyester Resin: Polyester composed of terephthalic acid, isophthalic acid, trimellitic acid, propylene oxide, bisphenol A, ethylene glycol Resin

Acid value: 10 mgKOH/g, hydroxyl value: 43 mg K0H/g, Tg: 58 ° C MMW : 28200, Μ : 2500 Molecular weight distribution of the binder resin and the following release agent (weight average molecular weight (Mw), number average molecular weight ( Μη)) was measured by GPC and by the following conditions. Device: GPC-150C (manufactured by Waters Co., Ltd.) Pipe column: GMH-HT30cm2 (made by Tosoh Corporation)

Temperature: 135 ° C Solvent: o-dichlorobenzene (. Add 〇. l% I 〇 N 〇 L) Flow rate: 1. 0 ml / min sample · 0. 15% of the sample is injected 〇. 4m 1 by the above conditions 'The molecular weight of the sample was calculated using a molecular weight calibration curve prepared from a monodisperse polystyrene standard sample. This 103 323045 201141957 is calculated by converting the polyethylene converted from the conversion formula derived from the Mrak-Houwink viscosity type. &lt;Preparation of colored resin composition&gt; Examples 154 to 175 and Comparative Examples 17 to 19 2500 g of a pigment composition or a monoazo pigment and 250 Å of a thermoplastic polyester resin were placed in a pressure kneader at a set temperature of 120. (:, 15 minutes, mixing, kneading, and then taking out. Then, kneading was carried out with 3 rolls of a roll temperature of 95 ' 'cooling and then coarsely pulverizing to less than 10 mm to obtain a colored resin composition. &lt;Toner Modifications> Examples 154 to 175 and Comparative Examples 17 to 19 4375 g of a thermoplastic polyester resin, 500 g of a colored resin composition, and a calcium salt compound (charge control agent) of 5-, 2-butyl salicylic acid 5 0 g, acetamidine homopolymer (release agent 'molecular weight 850, Mw / Mn = l. 〇 8, melting point 107 ° C) 75 g mixed with a Henschel mixer with a volume of 20 L (30 〇 0 rpm, 3 minutes ' Then the melt-kneading was carried out at a discharge temperature of 12 Torr using a two-axis kneading extruder. The kneaded material was then cooled and solidified, and then coarsely pulverized with a hammer mill Chafer mi 11), followed by a type I jet mill (IDS_2). Type) was finely pulverized' and then classified to obtain toner mother particles. Then, 25 〇〇g of the toner mother particles obtained above and a hydrophobic titanium oxide (STT-30AM2.5 g made by Titanium Industries Co., Ltd.) were mixed by a Henschel mixer of 1 L to obtain a negatively charged toner. Comparative Example 20 Changing the pigment composition or monoazo pigment to Hansa Brilliant 104 323045 201141957

Yellow 5GX (Clariant company j, r T, I U· Pigment Yellow 74),

The coloring resin composition and the toner were obtained in the same manner as in the examples 154 to 1M b and the comparative examples 17 to 19. &lt;Evaluation of Resin Composition and Toner&gt; Coloring Tree Residue (4) Coloring Agent (4) San (4) Xiangmachi Method was evaluated. Further, the image density, durability, and transparency of the toner were evaluated by the following methods. The results are summarized in Table 8. (Dispersibility) The sheet obtained by slicing the obtained colored resin composition and the toner was sliced by a microtome (miCrotorae), and the dispersion state of the pigment was observed by a transmission electron microscope, and the number of pigment agglomerates was determined according to the number of pigments collected. The evaluation of dispersibility was carried out. When the pigment aggregate was not confirmed, it was judged as ◎, and it was confirmed that 1 to 25 pigment aggregates were judged to be 〇, and it was confirmed that the pigment aggregate was determined to be Δ, and it was confirmed that 51 or more pigment aggregates were judged as X. . ^ (Image Concentration and Durability) Using a toner and a ferrite carrier (DFC-350C and Iron Powder Co., Ltd.) coated with a polyfluorene resin having an average particle diameter of 6 〇em as a carrier, The toner concentration was set to 6% to prepare a color developing agent. A color photocopying machine CLC-730 manufactured by Canon Inc. was used to output a monochrome image using each toner on a color application paper Ncolor 127 (A4 size, 127·9 g/m2) manufactured by Fujifilm Co., Ltd. as a photocopying paper. The image density after the initial measurement and after 10,000 sheets was measured, and the durability of the toner was evaluated. The image rolling was measured using the Gretag Macbeth densitometer D19C to determine the anti-323045 105 201141957 emission concentration of the print. (Transparency) After the developer obtained above forms a solid image on the 0 film, the 0 film formed with the solid image is again passed through the fixing portion of the photocopying machine to prepare a sample for flattening the image surface. The penetration is confirmed by visual judgment. The results of the visual judgment were evaluated as four stages of numbers 1, 2, 3, and 4. The larger the number, the better the transparency. 106 323045 201141957, [Table 8] Colored resin composition Toner used for toner composition Dispersibility image density transparency or initial 10,000-color dispersibility of single-even pigment Example 154 Pigment composition A 〇1. 38 1 35 〇 4 Example 155 Pigment composition _E 〇 1. 42 1. 42 〇 4 Example 156 Pigment technique G 〇 1.25 1.24 〇 3 Example 157 Pigment composition ◎ ◎ 1. 45 1. 43 ◎ 4 Example 158 Pigment Composition I ◎ 1. 43 1. 38 ◎ 4 Example 159 Pigment Composition R 〇 1. 45 1. 46 〇 4 Example 160 Pigment Composition S 〇 1.18 1.18 〇 3 Example 161 Composition ◎ ◎ 1. 38 1. 39 ◎ 4 Example 162 Pigment composition U ◎ 1. 29 1. 27 ◎ 4 Example 163 Pigment composition V 〇 1. 27 1. 24 〇 3 Example 164 Pigment composition Ff 〇1. 25 1. 19 〇3 Example 165 Pigment composition X 〇1. 33 1. 33 〇4 Example 166 Pigment composition Y 〇1. 34 1. 31 〇4 Example 167 Pigment composition C ◎ 1. 30 1. 32 ◎ 4 Example 168 Pigment composition d ◎ 1. 46 1. 45 ◎ 4 Example 169 Pigment composition e ◎ 1. 44 1. 45 ◎ 4 Example 170 Pigment composition g 〇1. 40 1. 42 〇3 Example 171 Pigment composition i 〇1. 39 1. 37 〇3 Example 172 Pigment composition k ◎ 1. 47 1. 44 ◎ 4 Example 173 Pigment composition p ◎ 1. 39 1. 37 ◎ 4 Example 174 Pigment composition W 〇. 1. 36 1. 36 〇 4 Example 175 Pigment composition X 〇1 37 1. 38 〇4 Comparative Example 17 Monoazo pigment AX 0. 92 0. 72 X 1 Comparative Example 18 Monoazo pigment D Δ 0. 75 0. 62 △ 2 Comparative Example 19 Monoazo pigment FX 0. 78 0. 64 X 2 Comparative Example 20 Hansa Brilliant Yellow 5GX Δ 0. 95 0. 74 Δ 2 107 323045 s 201141957 As shown in the results of Table 8, the composition of the colored resin prepared by using the pigment composition obtained by the present invention The substance showed good dispersibility compared to others. Further, the toner exhibits good dispersibility as compared with others, and also has good color developability and transparency. By the pigment composition containing a monoazo pigment obtained by the present invention, it is possible to provide a fine pigment composition which is improved in heat resistance which is a problem of a monoazo pigment, and which is excellent in dispersion stability. [Simple description of the diagram] None. [Main component symbol description] jfe 〇 i \ 108 323045

Claims (1)

201141957 V VII. Patent Application Range: 1. A pigment composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (2); (wherein X1 to Xs each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxycarbonyl group having a carbon number of 5 to 5, a carboxyl group, and a nitro group; a sulfonic acid group, an amine carbaryl group, an amine sulfonyl group, a difluoromethyl group, or a heterocyclic structure formed by combining adjacent groups; the phantom to X5 may have a substituent; and X6 to XlG each independently represent a hydrogen atom. a halogen atom, an alkyl group having a carbon number of i to 5, an alkoxy group having 1 to 5 carbon atoms, an acetamino group, a carboxyl group, a sulphate group, or a heterocyclic structure formed by combining adjacent groups; Χ6 to Χι 〇 may also have a substituent; Xu to xis each independently represents a hydrogen atom, a halogen atom, a carbon number of J to 5, an alkoxy group having 1 to 5 carbon atoms, an amine acetate group, an aryl group, 323045 1 201141957 sulfonate An acid group, a group represented by the following formula (3), or a group represented by the following formula (4); Χπ to X15 may have a substituent; however, at least one of Xh to χ15 is a formula (3) Any one of the groups shown in the formula (4); Formula (3) - Υ-Υ2-Υ3 (where Yi represents -S〇2NR' - or -C0NR', and R' represents Hydrogen atom, also An alkyl group having a carbon number of 20 or less having a substituent, an alkenyl group having a carbon number of 20 or less which may have a substituent, or an aryl group having a carbon number of 20 or less which may have a substituent; Y2 represents a bond of 丫1 and Y3 a direct bond, an alkylene group having a carbon number of 20 or less as a substituent, an alkenyl group having a carbon number of 20 or less having a substituent, or an exoaryl group having a carbon number of 20 or less having a substituent, Or -Y2a_Y2b-Y2c-; Y2a and Y2c each independently represent an alkylene group having a carbon number of 20 or less having a substituent, an alkenyl group having a carbon number of 20 or less having a substituent, or a substituent a aryl group having a carbon number of 20 or less; Y2b represents a direct bond of Y2a to Y2e, -0-, -CO---NR'-, or -S〇2-; only, R'-and Υι The definition is synonymous; Y3 represents _ORi, _COORi, _NRiR2, -CONRiR2, or -SO2NR1R2; Here, R1 and R2 each independently represent a hydrogen atom, an alkyl group having a substituent having a carbon number of 20 or less, An alkenyl group having 20 or less carbon atoms which may have a substituent, an aryl group having a carbon number of 20 or less having a substituent, or a heterocyclic structure formed by combining R! with hydrazine; or In R, Y2, and Y3 in Y!, R2 and R2 each independently represent a heterocyclic structure formed by combining R' and Y2 in Υι, or a combination of Y2 and R2 in 2, 323,045, 201141957 Y3 Heterocyclic structure); formula (4)? 丫6 (wherein Υ4 denotes -NR' - or -; Cao = each of the equations (5)... However, Y4, Y5, Y6 apply to R (5) - 丫 4 - 丫 2 - 丫 3 and equation (3) The definition is synonymous); &quot; 14 You Xing and the definition of the formula (4), such as the application of the scope of the patent scope of the first (four), the appropriate 3. = the content of the compound formula (1) The total amount of moles of the compound of the compound (4) which is not represented by the formula (2). The method for producing a pigment composition of the compound of the formula (2) a method of describing a pigment composition, the method comprising the steps of: nitriding an aromatic material to obtain a diazotide by 4, and (4) coupling a diazotide with a biphenylamine compound; wherein the aromatic amine The aromatic amine represented by the following formula (6) contains the ethyl benzene 323045 3 201141957 acetanilide compound represented by the following formula (7) and the acetamidine represented by the following formula (8). Ethyl anilide compound; formula (6) X4 X5 type (7) NHCOCH2COCH3 nhcoch2coch3 (Formula 1 to X1Q is synonymous with the formula (1), and Xu to 乂15 is synonymous with the formula (2)). A method for producing a pigment composition, which is a method for producing a pigment composition according to claim 1 or 2, which has a step of diazotizing an aromatic amine to obtain a diazotide, a step of coupling the diazotide with an acetophenone anilide compound 4 323 045 201141957; wherein 'the aromatic amine contains an amine of the formula: the acetophenone anilide compound contains the lower 埯6) An anthranilamide compound and an acetophenone represented by the formula (7) represented by the following formula (8); which have been combined with a acetylamine, and the method has the following steps: a heavy jut of a fragrant amine a step of adding an aromatic aniline compound of the formula to the aqueous solution, and performing a coupling reaction to obtain a reaction mixture; and reacting the reaction mixture with the acetophenone anilide compound represented by the formula (7); Χ12 Xu style (8) 5 323045 201141957 Xl2 Xl1 (Xi to XiD of the formula t is synonymous with the one defined by the formula (1), and Xn to 乂15 is synonymous with the one defined by the formula (2)). A method for producing a pigment composition, which is a method for producing a pigment composition according to claim 1 or 2, which has a step of diazotizing an aromatic amine to obtain a diazotide And a step of coupling the diazo compound to the acetanilide compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetaminophen compound has the following formula ( 7) an acetophenone anilide compound and an acetophenone anilide compound represented by the following formula (8); and the method has the following steps: in a buffer aqueous solution of pH 3 to 6, while The aqueous solution of the diazotide of the aromatic amine represented by the formula (6), and the acetophenone anilide compound represented by the formula (7) and the acetophenone anilide represented by the formula (8) are respectively added to the predetermined flow rate. a step of an alkaline aqueous solution of a compound; formula (6) 6 323045 201141957 Equation (8) Xl3 NHCOCH2COCH3 (wherein X1 to XlQ are synonymous with those defined by formula (1), and X11 to X15 are synonymous with those defined by formula (2)). 6. A method for producing a pigment composition, which is a method for producing a pigment composition as described in claim 1 or 2, which has a method of diazotizing an aromatic amine a step of obtaining a diazotide, a step of coupling the diazotide with an acetamidine compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), the acetamidine The aniline compound contains an acetamidine s 7 323045 201141957 acetophenone compound represented by the following formula (7); and the method has the following steps: a compound represented by the formula (2) and a formula (6) a step of mixing the diazotide of the aromatic amine to obtain a mixture; and reacting the mixture with the acetophenone anilide compound represented by the formula (7); Formula (7) (wherein Xi to X1Q are synonymous with those defined by formula (1)). 7. A method for producing a pigment composition, which is a method for producing a pigment composition according to claim 1 or 2, which has a step of diazotizing an aromatic amine to obtain a diazotide And a step of coupling the diazo compound to the acetanilide compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetaminophen compound has the following formula ( 7) 醯 8 323045 201141957 acetanilide compound; and the method has the following steps: the compound represented by the formula (2) and the acetophenone anilide compound represented by the formula (7) are subjected to the following steps: a step of mixing to obtain a mixture; a step of reacting the mixture with a diazotide of an aromatic amine represented by the formula (6); (6) 乂, Xi Formula (7) (where X! to χ1() are synonymous with those defined by equation (1)). A method for producing a pigment composition, which is a method for producing a pigment composition according to claim 1 or 2, which has a step of diazotizing an aromatic amine to obtain a diazotide And a step of coupling the diazotide with an acetamidine compound; wherein the aromatic amine contains an aromatic amine represented by the following formula (6), and the acetophenone compound contains the following formula (7) 醯 9 9 9 323 045 201141957 acetanilide compound; and the method has the following steps: in a buffer aqueous solution containing pH 3 to 6 of the compound represented by formula (2), at the same time a flow rate of adding an aqueous solution of an aromatic amine diazotide represented by the formula (6) to an alkaline solution of an acetophenone anilide compound represented by the formula (7); Formula (7) (乂之乂! The Xh system is synonymous with the one defined by the formula (1)). A method for producing a pigment composition, which is a method for producing a pigment composition according to claim 1 or 2, which has a step of diazotizing an aromatic amine to obtain a diazotide, a step of coupling the diazotide with an acetophenone anilide compound; wherein the aromatic amine contains an aromatic 10 323045 201141957 amine represented by the following formula (6), and the acetophenone anilide compound contains the following An acetanilide compound represented by the formula (7); and the method has the steps of: a diazotide containing an aromatic amine represented by the formula (6) and an acetamidine represented by the formula (7) a step of mixing a liquid of a reactant of an anilide compound with a compound represented by the formula (2); Formula (7) (1 in the formula! to X!. is synonymous with the one defined in equation (1)). A method for producing a pigment composition, which is a method for producing a pigment composition according to claim 1 or 2, which comprises the steps of: containing a compound represented by formula (1) and a step of wet-kneading a mixture of the compound represented by the formula (2) in the presence of a water-soluble inorganic salt and a water-soluble organic solvent; and subsequently removing the water-soluble inorganic salt and the water-soluble organic solvent from the mixture 323045 201141957 steps. The pigment composition according to the first or second aspect of the invention, wherein the compound represented by the formula (1) and the compound represented by the formula (2) have an average primary particle diameter of 200 nm or less. 12. The pigment composition according to any one of claims 1 to 2, wherein the specific conductivity of the aqueous solution obtained by boiling extraction of the pigment composition by ion exchange water is less than 200 #S/ Cm. 13. The pigment composition according to any one of claims 1, 2, 11 and 12, wherein the contents of t 'calcium, magnesium, and iron are not up to i5 (^pm, respectively). The pigment composition according to any one of items 1, 2, 11, 12, and 13, wherein the total content of calcium, magnesium, and iron is less than 300 ppm. 15. A pigment dispersion containing an application The pigment composition and the liquid medium according to any one of the items 1, 2, and 14 to 16. The inkjet ink containing the patent scopes 1, 2, u to 14 A pigment composition according to any one of the preceding claims, or a pigment dispersion according to claim 15. 17 - a coloring resin composition which contains any one of claims 1, 2, 11 to 14 The pigment composition and the binding resin according to the invention. 18. The toner for electrophotographic use, which comprises the pigment composition or patent application according to any one of the above claims 2, 11 to 14. The colored resin composition described in the scope of item 17. 323045 12 201141957 V IV. Designation of representative drawings: (1) The case The representative figure is: There is no picture in this case. (2) The symbol of the symbol of this representative figure is simple: No. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: (3) - Y "Y2 —Y3 formula (4) 3 323045