TW200813164A - Disazo pigment composition - Google Patents

Abstract

Disclosed is a disazo pigment composition characterized by containing a reaction product obtained by a coupling reaction of a diazo component composed of a tetrazonium salt of a compound represented by the general formula (I) below, a first coupling component composed of an acetoacetanilide compound and a second coupling component composed of a compound selected from the group consisting of an optionally substituted uracil, isocyanuric acid, barbituric acid and xanthine. [chemical formula 1] (I) (In the formula, R1, R2, R3 and R4 independently represent a hydrogen, a halogen, an alkyl group having 1-4 carbon atoms, an alkoxyl group having 1-4 carbon atoms or an alkoxycarbonyl group having an alkoxyl group having 1-4 carbon atoms.)

Description

200813164 IX. Description of the Invention: [Technical Field of the Invention] The present invention relates to a quinone azo pigment composition which can be suitably used for printing inks or paints and the like. [Prior Art] The so-called disazo pigment is a general term for a pigment having two gas heavy nitrogen groups in a molecular structure, but is mainly used for a pair of azo such as 3,3,-dichlorobenzidine. The salt is a general term of a yellow pigment (also referred to as disazo yellow) obtained by coupling a dinitrogen component to an even synthesis component comprising a N-acetamidine compound. In the present invention, the bisazo pigment means the general meaning of the latter. Such a double azo pigment is widely used for printing pigments in the fields of inks, paints, and plastics. The bisazo pigment is generally used in various fields of improvement in the above-mentioned field of use. For example, in the field of printing inks, it is known that the following improvements are made for the purpose of improving fluidity I or transparency. That is, in place of the former N-acetamidine anilide compound of the above-mentioned coupling component, a coupling reaction is carried out using an N-acetamidine anilide compound to which a specific substituent is introduced, and the bisazo compound thus obtained is mixed with the former The method of using the double-chaotic pigment (main pigment) (pigment mixing method), or by the coupling reaction, the previous N-acetamidine-aniline compound is used in combination with the heterogeneous N_ of the substituent A method of obtaining a compound of the pigment (mixed couple) or the like by using an ethyl acetophenone compound. Among such methods, the latter method (ie, mixed-coupled law) is excellent in productivity and relatively easy.

2075-9014—pF 5 200813164 Subjects with various requirements under controlled conditions have recently been researched and developed. For example, a method of introducing a water-soluble substituent to an N-acetamidine-aniline compound (Japanese Patent Laid-Open Publication No. SHO 49-1 05 822 (Patent Document 2) Or, as a substituent, a method of introducing a sulfhydryl group or a quinone imine group (Japanese Patent Laid-Open No. 59_〇〇8761 ^

Newspaper (Patent Document 3)). ～A These methods are proposed for the purpose of improving the flowability or transparency as described above, or the coloring power or heat resistance, but it is required to further enhance the characteristics of the disazo pigment. [Patent Document 1] Japanese Patent Laid-Open Publication No. SHO-A No. Sho. [Problem to be Solved] The present invention has been made in view of the above-described state of the art, and an object thereof is to provide a disazo pigment composition which further improves various properties such as transparency, %, coloring power, fluidity, and heat resistance. [Means for Solving the Problem] In order to solve the above problems, the results of the research are as follows. The coupling reaction is carried out as a coupling compound and an N-acetamidine aniline compound, and a specific compound having a basic structure is used to perform a coupling reaction. , can improve the transparency, gloss, tinting strength, fluidity, heat resistance and other characteristics of the knowledge, based on 2075-9014-PF 6 200813164 in this knowledge, further research and wear and then from the ~' later research and finally completed this inventor. That is, the present invention relates to a cadaveric and azo pigment composition characterized by comprising a diazo compound composed of a bisazo salt of a compound of the following formula (丨, 一, ^ ) Ingredients; N-ethyl acetonitrile, a poorly synthesized compound, a first coupling component; and a uracil, isocyanuric acid, barbituric acid, and a page selected from the group which can be represented by % # ^ /, having a substituent The reaction product obtained by the reaction of the 嗓 σ constituting the heterodyne:

阙2 takes the second coupling of R, Β (I) r R and R, which are hydrogen, halogen, carbon number of 1 to 4 carbon atoms of 1 to 4, or The alkyl group of R1 in the alkoxycarbonyl group of the alkoxy group having a carbon number of 丨4. The mixing ratio of the first coupling component to the second coupling component is preferably 85 m〇1% or more and 99 m〇1% or less, and the second coupling is preferably lm〇l% or more and 15 mol% or less. Further, in the above coupling reaction, it is preferred to use a third coupling synthesis comprising a compound of the following formula (11). The blending ratio of the third coupling component is 95 mol% or more and 99.9 mol% or less based on the total amount of the first coupling component and the second coupling component, and the third coupling is 0.1 mol% or more and 5 mol mol/min. The following is better.

• <Π) 2075-9014-PF 7 200813164 wherein R5 and R6 each independently represent hydrogen, a hydroxyl group, a methyl group, a methoxy group, a fluorenyl group, or an exact group, and R7 represents a methyl group or a decyloxy group. , ethyl, ethoxy, methoxycarbonyl or ethoxycarbonyl. Further, in the above coupling reaction, the fourth coupling synthesis of the compound represented by the following formula (in) or (IV) is further preferably used. The blending ratio of the first coupling component is the total of the second coupling component and the second coupling component, and the total coupling amount of the second coupling component and the third coupling component and the third coupling component is 85 m〇1. More than or equal to 99% by weight - the above fourth is preferably 1% by weight of 1% or more and 15% by mole or less.

丨丨I

0 0 II I NH C €Η^ C dj^ Side one ^, 丨, milk, Guojing, carbon number 1~4 yuan base, carbon number 1~4, Lu loaded ~ Gan „ , double i 4 Alkyl group, hydroxyl group, having a carbon number

The base of the sulfhydryl group, the brewing imine having the disc number of 4, the o-benzene ... has a carbon number! The base of the base of the base, the burntstone of the carbon number, the benzoate, the benzoate, the sulphate, the sulphate, or the sulphate. In addition, p8 g91() /, K Κ and R also contain two of them bonded to each other to become the sputum _, and further, the case of the formula (ίν) m and β1° respectively indicate that any benzene can be present. Ring replacement. Further, the above bisazo pigment composition contains a selected from the group consisting of c.

2075-9014-PF 8 200813164

Pigment Yellow 12 - C. I. Pigment Yellow 13 n q j

Pigment Yellow 14 , G. I· Pigment Yellow 17 , ς j

Pigment Yellow 55 - C. I. Pigment Yellow 81 &gt; q j

Pigment Yellow 83 ^ C. I. Pigment Yellow 87 ^ C. !

Pigment Yellow 152 &gt; C. I. Pigment Yellow 170 ^ C. i

Pigment Yellow 15 and c· L pigment: YeU〇w 16 is preferably a group of at least one pigment. [Effects of the Invention] The bisazo pigment composition of the present invention has at least one of characteristics such as transparency, gloss, coloring power, fluidity, heat resistance and the like as compared with the prior art. Promoter. Therefore, when the bisazo pigment composition of the present invention is used in various applications, it is extremely useful in industrial applicability because it can obtain a coloring material excellent in transparency, gloss, coloring power, fluidity, and heat resistance. In particular, when the bisazo pigment composition of the present invention is used in the field of one printing ink for its main use, it can be obtained by full-color printing of an ink film which is required to have high coloring power and excellent transparency. The requirement for high transparency and high tinting strength coexist. [Embodiment] Hereinafter, the present invention will be described in further detail. <Double azo pigment composition> The bisazo pigment composition of the present invention contains a reaction product obtained by coupling a diazo-forming knife and a post-coupled coupling reaction which will be described later. The reaction 2075-9014-pf q 200813164 product 'supplemented by the use of complex couples in the coupling reaction. Therefore, in the present invention, two or more types of reaction products of 2 K and even ruthenium pigments are produced. , 甘有如 <Diazo component> The diazonium component used in the present invention is a bis-azo salt of the following formula:

"(I) The structure of the mouth represented by the formula (1) of the basic gentleman can be used *, / has the chlorine or w... as described above, and is particularly limited, but especially the benzidine (the following formula (Ι) — υ), 3 r _ ^ with 3,3 2 2, 5 '-methoxybenzidine, or raw materials are easy to start.

G! In addition, the 'so-called bis-azo salt' system will be diazotized separately in the amine group, and the two methods of the tongue &amp; UU, the force diazotization are not particularly limited. Any pre-game know-how can be used. method. w』休用光 〈偶合成分&gt;

2075-9014-PF 10 200813164 The so-called "synthesis component" means a component in which a general coupling reaction reacts with the above-mentioned diazo component is used in the present invention. In other words, in the present invention, the first coupling component and the second coupling component, which will be described later, are used as an essential component, and the third coupling component and/or the fourth coupling component may be further used as desired. Further, the details of each couple component will be described later. Further, the coupling reaction is a reaction between a diazo component and an even component reaction or an azo compound (reaction product). In the case of the present invention, the coupling reaction is synthesized, due to the diazo component! The molecular theory theoretically reacts 2 molecules, so the blending amount of the coupling component is preferably 2 to 2·5 mol for the diazo component lm〇i. <Different 1 coupling component> The first coupling component of the present invention is composed of a compound of N-acetamidine anilide. Here, the N-ethylenic aniline-based compound is a compound of N-acetic acid anilide (the following (.) or a compound having a substituent of a phenyl group of N-acetamidine aniline. The substituent may be exemplified by a steroid, a methyl group, a methoxy group, an ethoxy group or the like, and may have a work type or two kinds of substituents on the oxime. In the present invention, 'as such a Ν 醯 醯 醯 醯 醯 醯 系The compound can be used without any particular limitation, and is a conventionally known bisazo pigment for use as a bismuth azobenzene compound. For example, the formula (C1_1) can be suitably used. (CBu 6) Any Ν-acetamidine aniline compound represented by +C +2075-9014-pp 11 200813164 ο

(G1H) ...(C1,2) ο Ϊ υ人 11丨丨 (Cl-3)

0 0 i! ϋ whcoh2coh0;

m c gh2 c 03⁄4 ¢01-5) OGH,

Further, as the first coupling component, one or two or more kinds of the above-mentioned N-acetylindanamine-based compounds can be used. <Second-synthesis component> The second-synthesis component of the present invention is a compound selected from the group consisting of urinary chlorination, isocyanuric acid, barbituric acid, and xanthene, which can have a substituent, 2075-9014 -PF 12 200813164 The stomach is used as such a couple of components. The second coupler is used as the second couple. The couple is synthesized. The gloss and tinting strength can be such that transparency, mobility, heat resistance and the like, that is, the previous double The azo pigment is usually obtained by simply coupling: the ground 'up J component with N-acetamidine aniline Li', and the diazonium to cause the above-mentioned dragon w+ coupling reaction. Any one or more of the characteristics fully demonstrate the required gender. For example, due to poor heat resistance, etc., it is a disadvantage of the fact that the heat is colored and the transparency is lowered during processing. There is also a disadvantage that the flowability of the ink is deteriorated due to the pigment structure. The present invention is the one that correctly solves such problems, and uses the N-acetamidine-aniline system and the compound as the coupling component! The even synthesis component, and different from the chemical structures (4) 2 couple synthesis points, successfully made the moon! · The characteristics of raw light, 着色, tinting strength, fluidity, heat resistance, etc. are leaps and bounds. Here, the uracil which may have a substituent means uracil (the following formula (C2-1)) or a urinary pyridine having a substituent, and a uracil having a substituent, and for example, a 5-mercapto group (hereinafter, Formula (C2-2)), 5-aminouracil (the following formula (C2-3)), 5-chlorouracil, 5-bromouracil, 5-fluorouracil, 5-nitrouracil, and the like.

2075-9014-PF 13 200813164

...(02r2)

...(G2 - 4)

Further, as such a second coupling component, one type or two or more types of the above compounds can be used. Further, the mixing ratio of the first coupling component to the second coupling component is preferably 85 mol% or more and 99 m〇U or less, and the second coupling composition is preferably lm 〇 1% or more and 15 m 〇 1% or less. The first coupling component is 90 mol% or more and 95 m〇i% or less, and more preferably the second coupling = 5 mol 1 % or more and 1 〇 m 〇 1% or less. In the case of mol%, there is a case where it is impossible to display more than l5m〇l% as described above, and the effect of the second coupling component of less than 1 on the surface of the raw material cost is unfavorable and economically unrealistic. <3rd synthesis score>

2075-9014-PF 14 200813164

M6 in the above formula (π) independently represents hydrogen, dentate methyl f-milyl, a few groups, or a fluoridyl group, and represents a methyl group, a p-oxy group, an ethyl group, an ethoxy group, and a methoxy group. A few or an ethoxy group. By combining such a third couple, the 盥 筮 筮 蚀 蚀 蚀 / / 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 It is preferable to use any of the compounds represented by the following formula (C3-5). The following formula (C3-4) is preferred for any compound represented by the formula (6) - 1) to (6) - 5).

As the compound represented by the above formula (11),

2075-9014-PF 15 200813164

Further, 'as a result of the above formula (1)). One or two types of the first coupling component can be used in combination with 帛2, and the ratio of the blending ratio is 99.9. 1% or less, so that the total amount of the above 3rd couples is 95% or more is good, for the first! Even if the composition is more than 1%, it is more than 1% of the public 7 ribs, 虮51 〇 % 1% or less, and the total amount of the compositing points is better than 3 ribs and 1% or less. The third coupling is 0.5 (four) 1% to the third mate. When 1% 〇1% is satisfied, there is a case where the improvement effect of the above characteristics cannot be exhibited, and if it exceeds -%, the raw material cost is unfavorable and economically unrealistic. <4th composite component> The present invention The coupling component may be combined with the above-mentioned oxime-coupled component and the oxime-coupled component in the coupling reaction, and a fourth coupling component composed of a compound represented by the following formula (Η!) or (IV) may be further used. The di-synthesis component may be used in combination with the above-described third-synthesis component, and may be used alone in combination with the first-synthesis component and the second-synthesis component without accompanying the third-synthesis component.

2075-9014-PF 16 -{III) ...(IV> 200813164

18, 1^, and 1^ in the above formula (111) or (^), each independently represents hydrogen, i, an alkyl group having 1 to 4 carbon atoms, an alkyl group having a carbon number of 4, An amidino group having a % of from 1 to 4, an alkylene group having an alkyl group having 1 to 4 carbon atoms, an phthalimide, an alkyl group having a carbon number of 4

An oxycarbonyl group, an alkoxysulfonyl group having an alkoxy group having 1 to 4 carbon atoms, a benzimidazole ketone, a carboxyl group, a carboxylate, a sulfonic acid group or a sulfonic acid salt. Further, R8, R9, and IT also include two of them bonded to each other to be Bmiazoleline (for example, as shown by the following formula (C4-5)). Further, in the case of the formula (Iv), r8, r9, and R each independently represent a phenyl ring-substituted one. Or adjust such a fourth coupling component, mainly for the purpose of adjusting the fluidity hue. Not any compound is preferred. (C4-3) using I: a compound represented by the formula (111) or (IV), especially

Use the following formula (C4-1) ~ formula (C4-7) table H00C

2075-9014-PF 17 200813164

(C4-4) * * * (04^5) ... (down to 7) Further, as such a fourth coupling component, one or two or more kinds of the above formula (Π I ) or (IV) can be used. a compound of the system. Further, the blending ratio can be used in the same ratio as the above second couple component. In other words, the total amount of the first coupling component and the second coupling component, or the total amount of the first coupling component, the second coupling component, and the third coupling component, g5m〇1〇/〇 or more, 99 mol% or less, 4 coupling is lm 〇 1% or more and 15 m 〇 l% or less, and the total amount of the first coupling component and the second coupling component, or the first coupling component, the second coupling component, and the third coupling component are combined. 90, 〇 1% or more and 95 m 〇 1% or less, and it is more preferable that the above-mentioned 4th VIII is 5 mol% or more and l〇m〇i% or less. Knife <Reaction product> The reaction product of the present invention is obtained by coupling the above-mentioned diazo component. In this hair /,, coupling; diazo component is azo

2075-9014-PF 200813164 Salt is a reaction product for the dimeric component of two molecules of the diazo component 丨 molecular reaction. Therefore, as the reaction product of the first coupling component and the second coupling component as the coupling component, it is expected that there will be a reaction product of one molecule of the diazo component and the first molecule of the two molecules. The reaction product of the diazo component of the molecule and the second coupling component of two molecules and the reaction product of one molecule of the diazo component and one molecule of the first coupling component and one molecule of the second coupling component are mixed and produced. / : 一一^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ Even synthesis and brother 3 couple synthesis time, as such a reaction product, it is expected that there will be one molecule of diazo component and two molecules of the first a reaction product of a coupling component, a reaction product of one molecule of a diazo component, a reaction product of two molecules of a second coupling component, a reaction product of one molecule of a diazo component, and a molecule of a third molecule of a third coupling component, and a weight of one molecule a reaction product of a nitrogen component with a first coupling component of one molecule and a second coupling component of one molecule, a reaction product of one molecule of a diazo component, a first coupling component of one molecule, and a third coupling component of one molecule, A reaction product of one molecule of a diazo component is mixed with a reaction product of a second coupling component of one molecule and a third coupling component of one molecule. When the first coupling component, the second coupling component, and the fourth coupling component are used as the coupling component, or when the first coupling component, the second coupling component, the third coupling component, and the fourth coupling component are used, the same can be expected. In other words, the reaction product of the present invention does not have a composition containing only a quinone, and it is necessary to mix two or more kinds of the reaction product. <Composition of bisazo pigment composition>

2075-9014-PF 19 200813164 The bisazo pigment composition of the present invention is characterized in that the composition contains two or more kinds of the above reaction products. Then, it is preferable that the reaction product is less than one type of pigment specified by C. I. Pigment No. (color index pigment number). That is, the bisazo pigment composition of the present invention contains a compound selected from C · I · P i g η e n seven Yellow 12 - C. I. Pigment Yellow 13 &quot; C. I. Pigment

Yellow 14 &gt; C. I. Pigment Yellow 17 &gt; C. I. Pigment

Yellow 55 - C. I. Pigment Yellow 81 ^ C. I. Pigment

Yellow 83 ^ C. I. Pigment Yellow 87 &gt; C. I. Pigment

Yellow 152 &gt; C. I. Pigment Yellow 170 ^ C. I. Pigment orange 15, and c· I· Pigment orange 16 The group consisting of at least one pigment is preferred. <Manufacturing Method> The bisazo pigment composition of the present invention contains a reaction product obtained by coupling the above diazo component with an even component, but the specific conditions of the coupling reaction are not limited, and the conventionally known one can be used. Any reaction conditions are fine. For example, a method in which a diazo component is incorporated into a weakly acidic slurry in which the euro is synthesized and acidified (acid precipitation coupling method), or a method in which a diazo component and an even component are simultaneously injected into a weakly acidic buffer solution ( Item Note) Here, the specific conditions for exemplifying the acid evolution couple are as follows. Namely, first, by coupling the aqueous solution of the coupling component, an aqueous solution such as acetic acid is added dropwise to adjust the coupling to a weakly acidic condition of 3 to 6.5 to analyze the coupling. Then, the hunting is carried out by mixing the aqueous solution of the diazo component slowly under the mixing.

2075-9014-PF 20 200813164 The applicant. The specific conditions for the injection of the even law at different times are as follows. In other words, a buffer solution having a weak acidity (pH 3 to 6·5) is prepared by using acetic acid or sodium hydroxide, and an aqueous solution of a diazo component and an aqueous solution of a dissolved coupling component are gradually dropped into a coupling reaction. In this case, it is preferred that the diazo component lm〇1 is added dropwise in an amount of 2 to 2·5 raol. <Embodiment> Hereinafter, the present invention will be described in more detail by way of examples, but the invention is not limited thereto. In addition, in the following description, "%" means % by mass unless otherwise specified. <Example 1 &gt; 1 69 parts of 3'3-diphenylbenzidine hydrochloride, 229 parts of 32% hydrochloric acid, and 4000 parts of water were stirred and then placed under ice flotation (the temperature was adjusted to ±2 °C) The bis-azo salt of the above formula (I-1) is added to the aqueous solution by adding water containing 96 parts of sodium nitrite, that is, by the formula (I) The diazo component of the bisazo salt of the compound represented by the compound). Hereinafter, this aqueous solution is referred to as a solution containing a diazo component. Further, s has a solution of diazo and contains a quinone diazo component. On the other hand, N-acetamidine (the above formula (CBu 1), the 丄e-f component) 238 parts, and the urine density (the above formula (C2-1), the second couple) 15 ^ is dissolved in the aqueous solution of the sodium hydroxide 87 and the hydrocyclone, and the aqueous solution is referred to as H containing the coupling component. The solution containing the coupling component is 0.13 mol. There is a brother 1 even 5 ingredients m, the first

207 5-9014-PP 200813164 Next, 70 parts of acetic acid, sodium hydroxide a: (4) (10), 30 parts of air emulsified sodium, and 5,000 parts of water were used. The solution containing the diazo component and the solution containing the coupling component were subjected to a coupling reaction with respect to the buffer solution. Speaking and then 'after the end of the coupling reaction' adjust the pH to 5. After adding the test compound of the pine scorpion, the sulfuric acid was further added to the 15 parts of the ruthenium. Then, after stirring for 3 G minutes after the MGt was heated, a filter cake having a water content of 73% was found by hydrazine and water. τ - the filter cake, which comprises the bisazo pigment composition of the present invention, contains a diazo component and a first! The coupling component of the coupling component and the coupling reaction of the second coupling component are: Further, the analysis was carried out by FD/MS (electric field deionization mass spectrometry) measurement, and it was confirmed that one type of the reaction product contained c. I. Pigment Yel1〇w 12 . <Example 2 &gt; In the example, except that the solution containing the even component is used as the coupling component, N-acetamidine aniline (the above formula (C1_n, the first coupling component "μ moiety (l, 32 mol), isocyanuric acid) (The above formula ((:2_4), the second coupling component Mg 2 (〇, .lm〇1), Xenon 2-chloro-5-Dendrobyl phenyl)-3-methyl-5-ton. The ketone (the above formula (C3-5), the third coupling component) 6.6 (O. 〇 2 mol), all other similarly obtained a filter cake having a water content of 72%. The filter cake comprises the double couple of the present invention. The nitrogen pigment composition includes a reaction product obtained by coupling a diazo component with a first coupling component, a second coupling component, and a third coupling component. Further, the same analysis as in Example 1 is carried out. It is confirmed that the species which is the reaction product contains c 2075-9014-PF 22 200813164 I· Pigment Yellow 12 实施 <Example 3> In Example 1, except that the solution containing the coupling component contains the N-acetyl group as the coupling component. Anhydroaniline (the above formula (ci-1), the first coupling component (1. 32 mol), isocyanuric acid (the above formula (C2-4), the second coupling component) 9 Part (0. 07mol), 5-acetylindolylbenzimidazole, j (the above formula (C4-5), the fourth coupling component), 15.5 (0·07πιο1), all other examples were obtained. a filter cake having a water content of 73%. The filter cake comprising the bisazo pigment composition of the present invention comprises a coupling reaction of a diazo component with a dimerization component, a second coupling component, and a fourth coupling component. In the same manner as in Example 1, it was confirmed that one of the reaction products contained c I· Pigment Yellow 12 in the same manner as in Example 1. <Example 4> In Example 1, except The solution containing the coupling component is used as a coupling component containing N-acetamidine aniline (the above formula (Cl-ι), the first coupling component) 238 (1·32 m〇l), 5-methyluracil (upper formula) (C2-2), 2nd octagonal, 8.6 parts (0.07m〇l), 3-methyl-1-(p-sulfophenyl)-5-pyrazolone (the above formula (C3-4) ), the third coupling component) 6· anthracene (〇·02mol), and p-ethoxy-N-acetoacetanilide (the above formula (C4—β), the fourth coupling component) 15 5 (0·07 mol) All others are equally Filter cake having a water content of 74%, the filter cake comprising the bisazo pigment composition of the present invention, comprising a diazo component, a first coupling component, a second coupling component, a third coupling component I, and a fourth coupling In the same reaction as in Example 1, it was confirmed that one of the reaction products was CI Pigment Yellow 12 by the same reaction as in Example 1 in the reaction product. <Example 5 &gt; 238 parts of N-acetic acid aniline (the above formula (ci-1), first coupling component) and uracil (15 of the above formula (C2-n, second coupling group) were dissolved. An aqueous alkali solution composed of 70 parts of sodium hydroxide and a portion of water iooo. Next, the pH of the weakly acidic aqueous solution of 94 parts of acetic acid diluted with 1 000 parts of water was added by instilling the aqueous solution for 30 minutes. The solution is adjusted to a weak acidic condition of 〇, and the crystal of the even component is precipitated. Hereinafter, the solution containing the precipitate is referred to as a solution containing the coupling component, and the solution containing the coupling component contains the ith coupling component 132 m〇1. The second coupling synthesis is 13m〇1. Then, the solution containing the coupling component is cooled to 5 ° C, and then the same diazo component-containing solution of Example 丨 is added dropwise for 3 hours by stirring. After the completion of the coupling reaction, the pH was adjusted to 5 · 〇, and the alkali compound of the rosin 21 was added, and then 5 parts of aluminum sulphate were further added. Then, the mixture was heated at 80 C for 30 minutes with stirring. Water is obtained by filtration and water washing 70% of the filter cake. The filter cake comprising the bisazo pigment composition of the present invention contains a reaction product obtained by coupling a diazo component with a first coupling component and a second coupling component. By performing the same analysis as in Example i, it was confirmed that the kind of the reaction product contained c·〗.

Ye 11〇w 12 〇2075-9014-PF 200813164 <Example 6 &gt; In Example 5, except that the solution containing the even component was used as a coupling synthesis to contain N-ethylamine (the above formula (ci-1) ), brother 1 couple synthesis) 2 3 8 parts (1·32mol), isocyanuric acid (formula (C2-4), 2nd synthesis) 13, 2 parts (O.lmol), 1-(2-chloro -5-Dendrobylphenyl)-3-methyl-5-. In comparison with the above-mentioned (the above formula (C3-5), the third coupling component), the sixth part (〇·〇2 mol), the filter cake having a water content of 71% was obtained in the same manner. The filter cake comprising the bisazo pigment composition of the present invention contains a reaction product obtained by coupling a diazo component with a first coupling component, a second coupling component, and a third coupling component. . Further, by performing the same analysis as in Example 1, it was confirmed that one of the reaction products contained c. I. Pigment Yellow 12 〇 <Comparative Example 1 &gt; In Example 1, instead of containing the coupling component Urea pyrimidine in solution. In the fifth part, the second part was used, and the second part was used in the same manner as in the first embodiment, except that 30 parts of the above formula (C4-1) were used (0·13 m〇i). A filter cake having a water content of 75% was obtained. The filter cake comprises a product of a coupling reaction of two kinds of coupling components composed of N-acetamidine aniline and 2 acetamidine benzoic acid, but the product is in that the invention is not used. The point of the second coupling component is different from the composition of the reaction product of the present invention. <Comparative Example 2 &gt; In the case of Beiga addition 1, instead of the uracil bite (the second component) contained in the solution containing the coupling component, 5-acetammonium benzimidazolone was used.

2075-9014-PF 25 200813164 (Partifier (C4-5)) 30 parts (〇.13 mol), and a filter cake having a water content of 74% was obtained in the same manner as in Example 1. The filter cake comprises a product of a coupling reaction of two kinds of coupling components composed of N-acetylindoline and 5-acetylamidobenzimidazolone, but the product is not used. The second coupling component of the present invention is different from the composition of the reaction product of the present invention. <Comparative Example 3> In Example 5, instead of the uracil (second coupling component) contained in the solution containing the coupling component, 1 - ethyl acetamidoaminobenzoic acid (the above formula (C4-1)) was used. In the same manner as in Example 5, 30 parts (〇·13m〇1) were obtained, and a filter cake having a water content of 72% was obtained. The filter cake comprises a product of a coupling reaction of two kinds of coupling components consisting of N-acetamidine and 2-ethylindenyl benzoic acid, but the product is in that the invention is not used. The point of the second coupling component is different from the composition of the reaction product of the present invention.

<Comparative Example 4> ^ M Court Example 5, in place of the uracil (diaster 2 coupling component) contained in the solution containing the coupling component, using 5-ethylindolylbenzimidazolone (the above formula (C4-) 5)) 30 parts (〇.13m〇1), all of which were obtained in the same manner as in Example i, to obtain a filter cake having a water content of 74%. a cake-based product comprising a coupling reaction of two kinds of coupling components consisting of N-acetamidine and 5-ethylidene-based benzophenanthrene in the absence of use of the present invention The composition of the reaction product of the present invention is different. 2075 to 90l4 to pp 26 200813164 <Inkization> The filter cakes obtained in the above Examples and Comparative Examples were inked by the following method. In other words, a varnish for lithographic ink (trade name: soybean oil-based varnish LS-151, manufactured by Tosoh Oil Co., Ltd.) heated at 50 ° C was filled in a flash kneader and further filled with a composition equivalent to diazo pigment. The conversion of the 1 〇〇 part of the filter ^ order flash. After the removal of the free water, 150 parts of the varnish for the lithographic ink was further optimally mixed. Then, after removing the water by vacuum dehydration for 1 hour at rc, the varnish for the lithographic ink was further added with the varnish 173.3 and the solvent (trade name: solvent No. AF-7; manufactured by Nippon Oil Co., Ltd.) 33 3 To prepare a matrix ink comprising (10) a disazo pigment composition. Then, by using 60 parts for the matrix ink, the varnish for the upper printing ink is added 3 5θ ?», +, 士士》, [J'35 °P and the above-mentioned solvent 5 parts to prepare an ink containing 9% of a disazo pigment composition. Hereinafter, various tests are carried out by using the ink. <H Colour 5 parity test> By using an RI tester (芮口我1 The company's 0-name name. RI_2 type; Ishikawajima Industrial Machinery (plate) system) The inks passed on the above-mentioned enamel are applied to art paper to evaluate transparency, gloss, and tinting strength. ^ ητ 冉, ink coating conditions For the roller of the RI RI tester, use a four-point /, ... .^ ^ ^ ^ °] rubber roll, which is implemented in each of the divided parts by 0. 125cc / by the condition of the ink. First, 'evaluation of transparency' For the white department and the black department, the central government: as the real world - the color of the Ministry of the #,. The ink is applied, and the ink is applied to the coating, and the transparency is visually observed. Specifically, the ink is applied.

2075-9014-PF 27 200813164 The more the cloth part can clearly see the blackness of the lower layer, the transparency is good, and the transparency is good, and the transparency is good. "β", ""', and those with poor transparency are evaluated as "," and the transparency is ".", UGV &quot;睪&quot;Bee by using a digital angle gloss meter (quote. Name. 卯V-4D, · _ testing machine ((Shang dynasty. 60 degree gloss and ping 俨 ^ 疋 - ink coated surface on the paper is right h "measurement" is the greater the value measured and has a good luster. Eight clothes do not have -_ and 'evaluation of tinting strength' 嶋TH reflection densitometer (face 4, · chat (share) system) measurement: name · Iraq. 兮, 日丨 A, work 97 / by ink coated surface and evaluation疋, the larger the value measured, the higher the coloring power. <Flowability Evaluation Test> After placing 2 cc of each ink on the glass plate, the glass plate was tilted at 60 degrees for 2 minutes. The flow distance of the ink after the heart & knife. The longer the flow distance, the better the fluidity. In the case of the above-mentioned kibe/manufactured by the ink, after mixing in a flash kneader at (10) ° C for 2 hours, 'the substrate ink was used to adjust the composition containing 9% of the bis-bisphenescent pigment in the same manner as described above. Then, the ink and the ink which was not kneaded with ruthenium for 2 hours (ink used for the above-described hue evaluation test, etc.) were respectively applied to art paper, and the hue of the two was visually observed - The heat resistance was evaluated. The smaller the difference in hue, the better the heat resistance, the "eight" for those having particularly excellent heat resistance, the "B" for those having good heat resistance, and the "G" for those having heat resistance. Poor heat resistance

2075-9014-PF 28 200813164 The evaluation was "D". The above test results are shown in Table 1 and extravagant Table 1

It is apparent from Tables 1 and 2 that the ink of the bisazo pigment composition of the present invention is blended between the same and the manufacturing method (Example): The ink of the column 'in terms of transparency, gloss, tinting strength, flow Among the items of the sex and the resistance, the excellent results were shown in the above four items. The former shows the preferred characteristics of the bisazo pigment composition material. The embodiments and examples of the present invention have been described above, ^

2075-9014-PF 29 200813164 It is intended that the above embodiments and the configurations of the embodiments are appropriately combined. The embodiments and examples disclosed herein are at all points, and are not intended to be limiting. The scope of the present invention is not limited to the above description, but is included in the field, and includes the meaning and scope of the application scope. [Simple diagram description] # %,, [Description of main component symbols] Benefit 2075-9014-PF 30

Claims (1)

200813164 X. Patent application scope: 1. A bisazo pigment composition characterized by comprising a diazo component composed of a bisazo salt of a compound represented by the following formula (1); N-acetonitrile a di-synthesis component composed of an anthranilamide-based compound; and a second coupling-synthesis coupling reaction selected from the group consisting of a compound having a substituent such as uracil, isocyanuric acid, barbituric acid, and xanthine; The resulting reaction product: The wipes independently represent chlorine, dentate, a carbon group, a carbon number η, or a carbon atom of a carbon atom. 2. The bisazo pigment composition according to the above-mentioned patent range, wherein the ratio of the first coupling component to the second coupling component is 85 atom% or more and 99_1% or less, and the coupling is made. It is 1 mol% or more and 15 ra 〇 1% or less. 3. The bisazo pigment composition as described in the above (4), item 2, is subjected to the above coupling reaction, and the third coupling group consisting of the following formula ((1) is used. 2075-9014-PF 31 200813164 wherein R5 and R6 are each independently hydrogen, halogen, methyl, decyloxy, carboxy or sulfo, and R7 is a non-methyl, oxirane Base, ethyl, ethoxy, methoxycarbonyl or ethoxycarbonyl. 4. The double azo pigment composition as described in claim 3, wherein the third coupler is divided into a ratio of the first coupler to the coupler, and the total number of the first coupled couples is 95. The rib is 1% or more and 99 9 is 1% or less, and the third coupling is made to be 〇. lm 〇 1% or more and 5 〇 % 1% or less f. 5. As described in any one of the claims Sutchu Gudi 1 to 4 The bisazo-pigment composition is in the above-mentioned two-in-one reaction, and further uses a fourth coupling component composed of a compound represented by the following formula (Hj) or (IV): 0 ^ ^HCO^CCH^ _ (ΠΙ) ... mad V) Gossip KK, and IT, respectively, independently represent hydrogen, dentate, alkyl with 1 to 4 carbon atoms, alkyl group with carbon number 丨~4, hydroxyl group, with carbon number 1~ a mercapto group of 4 alkyl, an anthracene having an alkyl group having a carbon number of 44, an phthalimide, an alkoxycarbonyl group having an alkyl group having 1 to 4 carbon atoms, having a carbon number of 4 Alkoxy alkoxysulfonyl, benzimidazolidinone, carboxyl, carboxylate, sulfonate, or sulfonate. Also, R8, R9, and. Also included are those in which two are bonded to each other to form an imidazolinone. Further, in the case of the formula (IV), V, R9, and R1G each independently represent a phenyl ring-substituted one. The bisazo pigment composition according to claim 5, wherein the blending ratio of the fourth coupling component is the same for the second coupling component and the second coupling The total amount of the components, or the total amount of the ith coupling component and the second coupling component and the third coupling component is 85 m〇1% or more and 99 m〇l% or less, and the fourth coupling is lm〇1% or more and 15_1〇. /〇The following. 7. The disazo pigment composition according to claim 1, wherein the disazo pigment composition comprises a color selected from CI pigment f - Yellow 12 &quot; CI Pigment Yellow 13 - CI Pigment Yellow 14 ^ CI Pigment Yellow 17 ^ CI Pigment Yellow 81 , CI Pigment Yellow 83 , CI Pigment Yellow 87 , C. I· Pigment Yellow 152 , CI Pigment Yellow 170 , CI Pigment Yellow 15 , and C· I· Pigment Yellow At least one pigment of 16 groups. 2075-9014-PF 33 200813164 VII. Designation of representative drawings: (1) The representative representative of the case is: No (2) The symbol of the symbol of the representative figure is simple: No / 8. If there is a chemical formula in this case, please reveal the best display. Chemical formula of the invention: No 2075-9014-PF 4