JP4802510B2 - Disazo pigment composition and method for producing the same - Google Patents

Description

  In the present invention, when added to water-based ink or water-based paint, it is difficult to foam, a dispersibility is good, and a colored product having high coloring power is obtained. I. The present invention relates to a disazo pigment composition containing Pigment Yellow 14 as a main component and a method for producing the same.

  C. I. Pigment Yellow 14 is an insoluble disazo pigment having a similar structure. I. Pigment yellow 12 and C.I. I. It is known to exhibit a greenish yellow color different from Pigment Yellow 13. And C.I. I. Since it is excellent in solvent resistance and light resistance as compared with CI Pigment Yellow 12, it is often used for the preparation of light packaging gravure printing ink and the like.

  There are two types of printing inks and paints, oily and water-based. Recently, water-based printing inks and paints are actively promoted due to problems of air pollution and work environment pollution. C. I. Since the insoluble disazo pigment represented by Pigment Yellow 14 has extremely high hydrophobicity, in order to stably disperse it in an aqueous medium, it is necessary to improve the hydrophilicity of the surface of the insoluble disazo pigment more than ever.

  As a method for improving the dispersibility in an aqueous medium by making the pigment surface hydrophilic, the pigment surface is conventionally coated with a nonionic surfactant that exceeds HLB13, such as polyoxyethylene nonylphenol ether. It was. However, the hydrophilicity of the pigment surface by this method is constrained by the fact that the surfactant used causes foaming of the water-based ink, so that the amount used is limited and the surface is made sufficiently hydrophilic. It was difficult. It was impossible to make the pigment surface sufficiently hydrophilic with such a surfactant alone.

On the other hand, in Patent Document 1, a nonionic surfactant having HLB 2 to 5 such as sorbitan distearate or sorbitan trioleate is mainly used, and a nonionic surfactant exceeding HLB13 is used in combination with this. The coating of the surface is described.
However, the viscosity at the time of ink dispersion is high, the dispersion with a high pigment content cannot be performed, and even when the pigment content is lowered and dispersed, there is a defect that the gloss and coloring power of the ink extended product are inferior.

Patent Document 2 describes that the surface of a pigment is coated with a nonionic surfactant composed of an ethylene oxide-propylene oxide adduct of ethylenediamine.
However, the viscosity at the time of ink dispersion is high, the dispersion with a high pigment content cannot be performed, and even when the pigment content is lowered and dispersed, there is a defect that the gloss and coloring power of the ink extended product are inferior.

In Patent Document 3, when an insoluble disazo pigment is produced by carrying out a coupling reaction in an aqueous medium in the absence of an organic solvent in one step, a turbid point in an aqueous solution state is required at the latest just before the pigment is isolated. It is described that the surface of a pigment is coated by adding a nonionic surfactant.
The nonionic surfactant having a turbidity point described in Patent Document 3 is a propylene oxide-ethylene oxide block copolymer or the like. However, the pigment whose surface is coated with these has gloss, transparency, and coloring of ink. None of the forces are untreated C.I. I. It was of the same quality as Pigment Yellow 14, and it was difficult to stably disperse it in an aqueous medium.

In Patent Document 4, in the production process of an insoluble disazo pigment, a Diels-Alder condensate of unsaturated polyvalent fatty acid and rosin is added to the coupler slurry, the pigment slurry after the coupling, or the dried pigment, and It is described that the surface of the pigment is coated by adding a nonionic surfactant as required.
However, the nonionic surfactant described in Patent Document 4 has a high viscosity at the time of ink dispersion, and cannot be dispersed with a high pigment content. There was a disadvantage that it was inferior in gloss and coloring power.

  Insoluble azo pigments are often synthesized in an aqueous system and are in a floc state in the pigment slurry. In order to remove the floc state, the surface of the pigment is coated with a nonionic surfactant. When used in water-based inks or water-based paints after drying and powdering after isolation, there is a drawback that their quality is worse than that of the pigment in a state before surface coating.

Accordingly, it is possible to obtain a colored product which is suitable for the preparation of water-based inks and water-based paints, which is difficult to foam and has good dispersibility in a medium to be colored and has a high coloring power. I. A disazo pigment composition containing Pigment Yellow 14 as a main component is desired.
Japanese Patent Laid-Open No. 61-111365 Japanese Patent Laid-Open No. 3-103480 JP-A-6-166826 JP-A-8-259828

  The present invention is suitable for the preparation of water-based inks and water-based paints, and has a good dispersibility in a medium to be colored and can give a colored product having high coloring power. I. It is an object to provide a disazo pigment composition containing Pigment Yellow 14 as a main component.

  The inventors have described C.I. I. As a result of diligent research to obtain a colored product having good dispersibility in a medium to be colored and high coloring power in a system mainly containing CI Pigment Yellow 14, a hydroxyl group as a hydrophilic group serving as an adsorption point for pigment molecules is obtained. A nonionic surfactant having a specific chemical structure and containing a relatively large amount of C.I. I. Pigment Yellow 14 and the above-mentioned problems can be solved by sufficiently neutralizing the acid component contained in the pigment until the pH value of the extract becomes alkaline, and such a pigment composition. It is found that the product can be easily manufactured by adding a nonionic surfactant having a specific chemical structure in the system prior to the filtration performed after the pigment is manufactured, and performing the heat aging of the pigment slurry in an alkaline manner. The present invention has been completed.

  That is, the present invention is C.I. I. It contains 99 to 95% of Pigment Yellow 14 and 1 to 5% of sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups, and is defined in Japanese Industrial Standard JIS K 5101-17-1. Provided is a disazo pigment composition for water-based ink or water-based paint having a pH value of 8-11.

  Further, the present invention is C.I. I. Manufacture of a disazo pigment composition for aqueous ink or aqueous paint containing 95 to 99% of Pigment Yellow 14 and 1 to 5% of sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups A method comprising coupling a tetrazonium salt of 3,3′-dichlorobenzidine and acetoacetic acid-o-toluidide to form C.I. I. Sorbitan fatty acid ester or polyoxyethylene containing 2 to 5 hydroxyl groups at any stage prior to filtration in a method for producing a disazo pigment composition for water-based inks or water-based paints that is Pigment Yellow 14, heat-aged and filtered and washed Provided is a method for producing a disazo pigment composition for water-based inks or water-based paints, which contains a sorbitan fatty acid ester and is heated and aged in an alkaline manner.

The disazo pigment composition of the present invention comprises C.I. I. It contains CI Pigment Yellow 14 and a nonionic surfactant having a specific chemical structure, and has a higher pH value than before. Therefore, when applied to water-based ink or water-based paint, it is difficult to foam and has good dispersibility in the medium to be colored. There is a particularly remarkable effect that a colored product having high coloring power can be obtained.
The method for producing the disazo pigment composition of the present invention is a disazo pigment composition that, when applied to water-based inks or water-based paints, is difficult to foam and has a good dispersibility in a medium to be colored and provides a colored product with high coloring power. There is an especially remarkable effect that the product can be manufactured more easily.

  The disazo pigment composition of the present invention has C.I. I. When the total of CI Pigment Yellow 14 and a sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups is 100%, C.I. I. It contains 99 to 95% of CI Pigment Yellow 14 and 1 to 5% of sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups.

  C. I. Pigment Yellow 14 is a known and commonly used insoluble disazo pigment, and is made of a substance represented by the following formula.

  The disazo pigment composition of the present invention contains a sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups. These are C.I. I. Pigment Yellow 14 adsorbed to form aggregates (floc). I. It is used to make Pigment Yellow 14 easier to unravel with a weaker force. Some sorbitan fatty acid esters do not contain hydroxyl groups, but in order to obtain the effects of the present invention, it is preferable to contain more hydroxyl groups that are effective hydrophilic groups that serve as adsorption points to pigment molecules. A sorbitan fatty acid ester containing 2 to 5 hydroxyl groups is selected and used. Examples of the sorbitan fatty acid ester containing 2 to 5 hydroxyl groups include substances represented by the following formula. In the formula, R is an alkyl group or an alkenyl group which may have a branch having 10 to 24 carbon atoms.

  Examples of the sorbitan fatty acid ester containing 2 to 5 hydroxyl groups include sorbitan monostearate (R = C17H35), sorbitan monooleate (R = C17H33), sorbitan monopalmitate (R = C15H31), and the like.

  Although some polyoxyethylene sorbitan fatty acid esters do not contain a hydroxyl group, a polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups is selected and used for the same reason as the sorbitan fatty acid ester. Examples of the polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups include substances represented by the following formula. In the formula, R is as defined above, and m, l, and n are all the number of repeating units of polyoxyethylene, and the total thereof is m + 1 + n = 15-30.

  Examples of the polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups include polyoxyethylene (6) sorbitan monolaurate (R = C11H23) and polyoxyethylene (20) sorbitan monolaurate (R = C11H23). Polyoxyethylene (20) sorbitan monopalmitate (R = C15H31), polyoxyethylene (6) sorbitan monostearate (R = C17H35), polyoxyethylene (20) sorbitan monooleate (R = C17H33), etc. Can be mentioned. Here, the numbers in parentheses are the sum m + l + n of the number of repeating units of polyoxyethylene.

  These sorbitan fatty acid esters containing 2 to 5 hydroxyl groups and polyoxyethylene sorbitan fatty acid esters containing 2 to 5 hydroxyl groups may be used alone or in combination. Hereinafter, a sorbitan fatty acid ester containing 2 to 5 hydroxyl groups and a polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups are collectively abbreviated as fatty acid esters.

  The fatty acid ester may have any HLB value. For example, polyoxyethylene (6) sorbitan monolaurate, polyoxyethylene (20) sorbitan monolaurate, polyoxyethylene (20) When the HLB 13-17, such as sorbitan monooleate, is used for the preparation of a water-based ink, it is preferable because plate fogging during printing hardly occurs and the laminate strength resistance as a coating film property becomes better.

  The disazo pigment composition of the present invention has a pH value of 8 to 11 as defined in Japanese Industrial Standard JIS K 5101-17-1. This standard defines a test method for measuring the pH of an aqueous suspension using a pH measuring device after boiling the aqueous suspension of the pigment and allowing it to cool to room temperature. By this test method, it is possible to estimate the presence and amount of acid or alkali that may be inevitably contained in the dry pigment.

  In general, insoluble disazo pigments are in a floc state in the pigment slurry for synthesis in an aqueous system, and the coupling reaction is carried out with weak acidity, so that this acid is easily taken into the floc. The acid present on the surface of the floc can be removed by subsequent cleaning, but it is difficult to sufficiently remove the acid existing inside the floc. Even if it is an acid inside the floc that is difficult to elute under normal conditions, the acid may elute outside as a result of exposure to wet heat conditions and the like, which may cause corrosion. In Japanese Industrial Standard JIS K 5101-17-1, since the pigment water suspension is boiled, it becomes possible to more accurately grasp the acid inside the floc that is difficult to elute under normal conditions. In the pigment composition of the present invention, more alkali than C.I. I. By including it in CI Pigment Yellow 14, the pH value defined in Japanese Industrial Standard JIS K 5101-17-1 was adjusted to 8-11.

  As this alkali, for example, ammonia or organic amine may be used, but the generated salt can be removed more easily by washing with water, and there is no fear of the salt returning to acid by volatilization. It is preferable to use an alkali metal hydroxide such as potassium.

  If necessary, the disazo pigment composition of the present invention may contain C.I. in a range that does not hinder the preparation of water-based inks and water-based paints and film properties. I. You may contain other yellow disazo pigments other than pigment yellow 14, surfactants other than the said fatty acid ester, rosins, and the like.

  C. I. Examples of other yellow organic pigments other than CI Pigment Yellow 14 include C.I. I. Pigment yellow 12, C.I. I. Pigment yellow 13, C.I. I. And CI Pigment Yellow 83. These can be contained alone or in combination of two or more in the disazo pigment composition of the present invention.

  Examples of the surfactant other than the fatty acid ester include polyethylene glycol monoalkyl ether, alkylbenzene sulfonate, polyoxyalkylene alkyl ether phosphate, and the like. These can be contained alone or in combination of two or more in the disazo pigment composition of the present invention.

  Examples of the rosins that can be contained in the disazo pigment composition of the present invention include all known and commonly used rosins. For example, rosins mainly composed of abietic acid, disproportionated rosins, partially hydrogenated rosins, Examples include fully hydrogenated rosin, maleic acid-modified rosin, fumaric acid-modified rosin, polymerized rosin, and water-insoluble salts thereof.

  The disazo pigment composition of the present invention has a C.I. value of 8 to 11 defined in Japanese Industrial Standard JIS K 5101-17-1. I. Pigment Yellow 14 and the fatty acid ester may be prepared by appropriately mixing so as to have the above-described mass ratio, but a tetrazonium salt of 3,3′-dichlorobenzidine and acetoacetic acid-o-toluidide are coupled. C. I. In the method for producing a disazo pigment composition for water-based inks or water-based paints, which is Pigment Yellow 14 and heat-aged and filtered and washed, C.I. I. The necessary amount of each raw material for the coupling reaction is used so that the pigment yellow 14 and the fatty acid ester have the mass ratio described above, and the necessary amount of the fatty acid ester is contained in an arbitrary stage before filtration. By carrying out heat aging in an alkaline manner, C.I. I. It is preferable in that the pigment yellow 14 and the fatty acid ester can be mixed and coated more uniformly.

  In this production method, disazo pigments are produced in accordance with a conventional method, heated and aged, filtered and washed. I. In the production method of CI Pigment Yellow 14, the C.I. I. When the total of the pigment yellow 14 and the fatty acid ester to be contained is 100% in terms of mass, the fatty acid ester is contained in an amount of 1 to 5%, and heat aging is performed in an alkaline manner.

  Here, as an optional stage before the filtration containing the fatty acid ester, for example, an aqueous suspension or aqueous solution of the raw material before the coupling reaction, a reaction liquid during the coupling reaction, after the coupling reaction and before heat aging, Examples thereof include an aqueous suspension during heat aging and an aqueous suspension after heat aging.

Next, C.I. I. The coupling reaction for producing Pigment Yellow 14 will be described in detail. In this coupling reaction, a tetrazonium salt of 3,3′-dichlorobenzidine is reacted with acetoacetic acid-o-toluidide.
As 3,3′-dichlorobenzidine and acetoacetic acid-o-toluidide, any known and commonly used ones can be used, but it is preferable to use high-purity products as much as possible. 3,3′-Dichlorobenzidine can also be used as the hydrochloride.

  The diazo component may be only the tetrazonium salt of 3,3′-dichlorobenzidine, but if necessary, the diazo component may contain other aromatic amines within 15 mol% of the total diazo component. Tetrazonium salts and diazonium salts can be included.

  The coupler component may also be only acetoacetic acid-o-toluidide, but if necessary, within 15 mol% of the coupler component, this coupler component may include acetoacetanilide, acetoacetate-m-xylide, etc. Can be included.

  As the tetrazonium salt of 3,3′-dichlorobenzidine, an aqueous solution or a water suspension prepared according to a conventional method can be used. By reacting 3,3′-dichlorobenzidine, hydrochloric acid and nitrite at a low temperature, an aqueous solution or suspension of a diazo component containing the corresponding tetrazonium salt is obtained. As acetoacetic acid-o-toluidide, an aqueous solution prepared according to a conventional method can be used. An aqueous solution of a coupler component is obtained by dispersing acetoacetic acid-o-toluidide in water by dissolving it in water.

  By coupling the diazo component and the coupler component thus obtained in the presence of the fatty acid ester according to a conventional method, C.I. I. An aqueous suspension of Pigment Yellow 14 can be prepared. At this time, the coupler component may be added to the diazo component, or the diazo component may be added to the coupler component, but the coupler component and the diazo component may be added to water.

  In the presence of the fatty acid ester, a tetrazonium salt of 3,3′-dichlorobenzidine and acetoacetic acid-o-toluidide were coupled to form C.I. I. When Pigment Yellow 14 is produced, the fatty acid ester is present when the pigment molecule is formed. As a result, the fatty acid ester is sufficiently adsorbed not only by the pigment molecule outside the flock but also by the pigment molecule inside the flock. In the dispersion during the preparation of the water-based paint, excellent dispersibility and dispersion stability can be exhibited even when the particle size becomes fine.

  As a method for coupling 3,3′-dichlorobenzidine tetrazonium salt and acetoacetic acid-o-toluidide in the presence of the fatty acid ester, for example, 3,3 ′, which is a raw material for performing a coupling reaction, is used. -There is also a method in which a tetrazonium salt of dichlorobenzidine, acetoacetic acid-o-toluidide, or both of these are mixed and reacted with the other, but in the water containing the fatty acid ester, 3, 3 ' -The method of coupling by adding the tetrazonium salt of dichlorobenzidine and acetoacetic acid-o-toluidide can coat the surface of disazo pigment from the side where primary particles are formed, and has better dispersibility and dispersion stability. This is preferable because it can be achieved.

  In addition, the buffer which can be used together in order to perform a coupling reaction can be prepared by, for example, in-system synthesis such as sodium acetate. The buffer is preferably adjusted to pH 4-6. In the case of performing a coupling reaction by adding a coupler component and a diazo component to water, a buffering agent is preferably used in combination.

  The reaction conditions for obtaining the disazo pigment by the coupling reaction may be in accordance with known and usual conditions, and are not particularly limited, but are usually performed at a temperature of 0 to 30 ° C. for 30 minutes to 3 hours. I can do it.

  C. I. The disazo pigment aqueous suspension containing Pigment Yellow 14 and the fatty acid ester as essential components is adjusted for pH as necessary, and is, for example, 50 ° C. or higher and lower than boiling point, preferably 70 ° C. to boiling point, according to a conventional method. The particle size, distribution, etc. of the pigment particles can be adjusted by heating for less than a predetermined time and aging. The heating time is not particularly limited, but is, for example, 30 minutes to 5 hours, preferably 45 minutes to 3 hours. Such heat aging is preferably performed on the aqueous suspension of the disazo pigment adjusted to pH 9-12. At this time, by aging with alkalinity, not only the acid outside the floc but also the acid inside the floc can be neutralized into a salt form, and further alkaline, This is preferable because the storage stability of a water-based ink or water-based paint using a combination of a film-forming resin containing a group and a basic compound can be improved.

  This alkaline heat aging, combined with filtration washing described later, is the most effective means for setting the resulting disazo pigment composition to a pH value of 8 to 11 as defined in Japanese Industrial Standard JIS K 5101-17-1. It is.

  The aqueous suspension of the disazo pigment that has undergone aging can be made into a wet disazo pigment composition such as a wet cake or slurry by filtering or washing with water. By repeating filtration and washing with water, the pH can be lowered compared to that at the time of ripening, and the pH can be neutralized, and purification can also be performed. In washing with water, hot water may be used, or an alkaline dilute aqueous solution may be used if necessary. It is preferable that the acid contained inside and outside the pigment particles is surely neutralized to be in the form of a salt in order to further improve the dispersion stability of the pigment particles in a water-based ink or water-based paint described later.

  By drying the disazo pigment composition in a wet state, a disazo pigment composition in a dry state such as powder or granule can be obtained. The dried disazo pigment composition in the form of a lamp can also be pulverized. In addition, the disazo pigment composition in a dry state can be narrowed in particle size distribution by classification.

  The disazo pigment composition of the present invention is used in various known and conventional applications, for example, printing inks such as lithographic printing inks, gravure printing inks, flexographic printing inks, paints, colored plastic molded products, etc., for electrostatic image development It can be applied to high-tech applications such as toners, color filters, and water-based inks for ink jet recording.

  The disazo pigment composition of the present invention comprises C.I. I. Since the fatty acid ester having pigment yellow 14 as a main component and more excellent in hydrophilicity is contained, it is particularly suitable for the preparation of water-based ink or water-based paint.

  From the disazo pigment composition of the present invention and an aqueous vehicle, aqueous inks and aqueous paints can be suitably prepared. This aqueous vehicle mainly contains a film-forming resin for fixing and fixing a pigment on a substrate when the solvent is volatilized, and water as a solvent. In addition, aqueous | water-based means the liquid medium in which a liquid medium contains only water or 60% or more of water by mass conversion.

  Examples of film-forming resins for preparing water-based inks include polyamide resins, styrene resins, maleic resins, acrylic resins, nitrocellulose, ethyl cellulose, cellulose acetate, ethylene-vinyl acetate copolymer resins, polyurethane resins, and polyesters. A water-soluble or water-dispersible resin such as a resin or a mixture of two or more of these may be mentioned.

  When a film-forming resin containing a carboxyl group and a basic compound are used in combination, an aqueous vehicle in which the film-forming resin is stably dissolved or dispersed in water can be formed. Examples of the basic compound include inorganic bases such as sodium hydroxide, potassium hydroxide and ammonia, and organic bases such as diethylamine, triethylamine and diethanolamine. A suitable aqueous vehicle for preparing an aqueous ink contains a basic compound and a styrene- (meth) acrylic acid ester- (meth) acrylic acid copolymer as a film-forming resin.

  The water-based ink can be prepared by mixing the disazo pigment composition of the present invention, the water-based vehicle, water, and other hydrophilic organic solvent, extender pigment, auxiliary agent and the like.

  Examples of the hydrophilic organic solvent include ethanol, methanol, isopropanol (IPA), acetone, ethyl acetate, ethyl lactate, cellosolve, diacetone alcohol and the like. Examples of extender pigments include barium sulfate, barium carbonate, calcium carbonate, silica, talc, calcium silicate, and precipitated magnesium carbonate. Examples of other auxiliary agents include waxes, surfactants, antifoaming agents, plasticizers, ultraviolet inhibitors, antioxidants, antistatic agents and the like.

Water-based paints can be prepared in substantially the same manner as water-based inks.
Examples of the film-forming resin for preparing the water-based paint include alkyd resins, silicone resins, fluororesins and the like in addition to the above-described resins. In order to increase the coating strength, a curing agent can be used in combination with the film-forming resin. Examples of such a curing agent include melamine resin, urea resin, polyisocyanate, and the like. Moreover, as a thickener used as an adjuvant, carboxymethylcellulose, polyvinylpyrrolidone, polyvinyl alcohol, etc. are mentioned, for example.

  The water-based ink and the water-based paint are, in terms of mass, for example, 10 to 50 parts of a film-forming resin, 30 to 80 parts of a liquid medium containing water, and 1 to 25 parts of the disazo pigment composition of the present invention. Thus, it can be prepared so that the total amount including the adjuvant becomes 100 parts and low viscosity suitable for printing and painting.

  The yellow water-based ink thus obtained can be used in combination with known and commonly used red or indigo water-based inks to print intermediate or full-color images by subtractive color mixing.

  Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. In addition, the part and% in an example are a mass reference | standard.

1.186 mol of 300 parts of 3,3′-dichlorobenzidine dihydrochloride (solid content: 100%) is charged into 1000 parts of water with stirring, and 371 parts of 35% hydrochloric acid are charged at the same time. Adjust the volume and temperature with ice and water. 559 parts of 30% sodium nitrite is added and tetrazotized. Excess nitrous acid is eliminated with sulfamic acid, and the solution after filtration is made into a solution containing a tetrazonium salt (an aqueous solution of a diazo component).
Separately, 476 parts of acetoacetic acid-o-toluidide as a coupler is dispersed in 2500 parts of water and dissolved with 20% caustic soda to obtain an aqueous solution of the coupler component.
Put 10,000 parts of water in a separately prepared container for coupling reaction, 53 parts of 80% acetic acid and Rheodor TW-O120V (Kao Co., Ltd. polyoxyethylene sorbitan monooleate. HLB = 15.0 Repeat of polyoxyethylene The total number of units is 15-30.) Add 23 parts and stir and mix. Next, the addition of the aqueous solution of the coupler component is started, and after preparing a sodium acetate buffer solution, the aqueous solution of each component is simultaneously added dropwise under the control of pH 5 and temperature of 20 ° C., and a coupling reaction is performed, whereby the pigment composition Was synthesized.
After pigment synthesis, the pH of the pigment slurry was adjusted to pH 10 by adding 20% sodium hydroxide. The temperature was raised, the temperature was kept at 90 ° C. for 60 minutes, and alkali aging was performed.
The finished pigment slurry was filtered to separate a water-washed pigment wet cake. The isolated pigment wet cake was dried at 110 ° C., and the dried lamp was pulverized with a juicer to obtain a powder of a yellow pigment composition.
In addition, about this pigment composition, it was pH 8.8 when pH of the extract was measured by Japanese Industrial Standard JIS K5101-17-1.

Similarly to Example 1, the diazotization liquid and the coupler solution were separately prepared.
In the coupling reaction vessel, the same amount of Rhedol Super SP-L10 (Kao Corporation sorbitan monolaurate, HLB = 8.6) was used instead of Rheodor TW-O120V (Kao Corporation) of Example 1. All other operations were carried out in the same manner as in Example 1 to obtain a yellow pigment composition powder.
For this pigment composition, the pH of the extract was measured according to JIS K5101-17-1 and found to be pH 9.0.

[Comparative Example 1]
Similarly to Example 1, the diazotization liquid and the coupler solution were separately prepared.
In the container for the coupling reaction, only 10,000 parts of water and 53 parts of 80% acetic acid were prepared, and the subsequent operations were all carried out in the same manner as in Example 1, and the yellow C.I. I. Pigment Yellow 14 pigment was obtained.
In addition, about this pigment composition, when pH of the extract was measured according to Japanese Industrial Standard JIS K5101-17-1, it was pH8.5.

[Comparative Example 2]
The same operation as in Example 2 is performed until the pigment slurry synthesis after the coupling reaction.
Adjustment to pH 10 was not performed, the temperature increase was started at pH 5, and the temperature was kept at 90 ° C. for 60 minutes. The operation after filtration was performed in the same manner as in Example 1 to obtain a yellow pigment composition. .
In addition, about this pigment composition, when pH of the extract was measured according to Japanese Industrial Standard JIS K5101-17-1, it was pH 5.5.

[Comparative Example 3]
In the same manner as in Example 2 above, the synthesis is performed until the synthesis of the pigment slurry, and the pH is not adjusted, but 23 parts of Rhedol Super SP-L10 is added to the pigment slurry of pH 5, and the temperature is increased. All subsequent operations were performed in the same manner as in Example 2 to obtain a yellow pigment composition.
With respect to this pigment composition, the pH of the extract was measured according to Japanese Industrial Standard JIS K5101-17-1, and it was pH 6.0.

[Comparative Example 4]
Similarly to Example 1, the diazotization liquid and the coupler solution were separately prepared.
In the coupling reaction vessel, the same amount of Neugen ET-102 (Daiichi Kogyo Seiyaku Co., Ltd., polyoxyethylene lauryl ether) was used instead of Rheodor TW-O120V (Kao Corporation) of Example 1, and the others. These operations were all carried out in the same manner as in Example 1 to obtain a yellow pigment composition powder.
In addition, about this pigment composition, when pH of the extract was measured according to Japanese Industrial Standard JIS K5101-17-1, it was pH 9.1.

[Comparative Example 5]
In the same manner as in Example 2 above, the synthesis was performed until the pigment slurry was synthesized, and adjustment to pH 10 was not performed. 23 parts of Emanon CH-80 (Kao Co., Ltd. polyoxyethylene hydrogenated castor oil) was added to the pigment slurry at pH 5, Start heating up. All subsequent operations were carried out in the same manner as in Example 1 to obtain a yellow pigment composition.
In addition, about this pigment composition, it was pH5.6 when pH of the extract was measured by Japanese Industrial Standard JISK5101-17-1.

Preparation method of aqueous gravure printing ink 16 parts of each powder pigment composition obtained in Examples 1 and 2 and Comparative Examples 1 to 5 and paste meat varnish [John Crill (registered trademark) 61J / Johnson Polymer Co., Ltd./distilled water] / IPA = 30/30/5 (mass ratio) mixed product] 38 parts and 160 parts of 3 mm glass beads are weighed in a 250 ml polybin, and dispersed for 60 minutes with a paint conditioner manufactured by Toyo Seiki Co., Ltd. 84 parts of John Crill (registered trademark) 74J manufactured by Johnson Polymer Co., Ltd. was added and dispersed for 5 minutes to obtain an aqueous gravure printing ink (hereinafter referred to as primary color ink). The inks of the examples were easy to prepare with little foaming.
On the other hand, in a 100 ml polybin, 20 parts of Daiflex Astia (registered trademark) D250 [white ink manufactured by Dainippon Ink & Chemicals, Inc.] and 4 parts of the above primary color ink are weighed and mixed with the above paint conditioner for 30 minutes. Hereinafter, this is referred to as light color ink.).

Evaluation method (gloss, transparency, tinting strength)
On art paper with black background, No. With a 6 bar coater, the primary color ink is developed, and after natural drying, the Gretag density meter SPL50 manufactured by Gretag, the spectrophotometer Microflash 200d manufactured by Datacolor, and the gloss meter (60 ° gloss) manufactured by BYK-Chemie Japan are used. Measure the color development surface. Similarly, light-colored ink was also developed and the coloring power was measured with a spectrophotometer. The results are shown in Table 1.
In addition, about the coloring power, the coloring power of each ink when the coloring power of the printed image in the ink prepared from the pigment composition of the comparative example 1 was made into 100% was displayed. Transparency is high when the black color of art paper is measured and the B value is large.

  In addition, when it was going to prepare water-based gravure printing ink using the pigment composition of Example 1 and 2, compared with the case where it was going to prepare water-based gravure printing ink using the pigment composition of Comparative Examples 2-5. The foaming was suppressed. When actual printing was performed with the aqueous gravure printing ink prepared using the pigment composition of Example 1, it was more suitable for plate fogging than the aqueous gravure printing ink prepared using the pigment composition of Example 2. The laminate strength was remarkably excellent.

The aqueous gravure printing ink prepared using the pigment composition of Example 1 of the present invention was manufactured using the pigment composition of Comparative Example 1 and polyoxyethylene lauryl ether manufactured without using a surfactant. In addition, it is clear that both the gloss and the transparency and coloring power are remarkably superior to the aqueous gravure printing inks prepared from the pigment composition of Comparative Example 4, respectively.
An aqueous gravure printing ink prepared from the pigment composition of Example 1 prepared using polyoxyethylene sorbitan fatty acid ester was prepared from the pigment composition of Example 2 prepared using sorbitan fatty acid ester as well. It is clear that the water-based gravure printing ink is superior not only in gloss but also in transparency and coloring power.
The aqueous gravure printing ink prepared from the pigment composition of Example 2 in the region where the pH is higher in JIS K5101-17-1, in which the heat aging was performed with alkalinity, was heat aging as usual without adjusting the pH. It is clear that the coloring power is superior to the aqueous gravure printing inks prepared from the pigment compositions of Comparative Example 2, Comparative Example 3 and Comparative Example 5 having a lower pH in JIS K5101-17-1. It is.

Claims (6)

In terms of mass, C.I. I. 95 to 99% of CI Pigment Yellow 14, 2 to 5 hydroxyl groups, 1 to 5% of sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester, and a pH value defined in JIS K 5101-17-1 A disazo pigment composition for water-based ink or water-based paint, which is 8-11. The disazo pigment composition for water-based inks or water-based paints according to claim 1, wherein the sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups is a polyoxyethylene sorbitan fatty acid ester of HLB 13-17. In terms of mass, C.I. I. Manufacture of a disazo pigment composition for aqueous ink or aqueous paint containing 95 to 99% of Pigment Yellow 14 and 1 to 5% of sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups A method comprising coupling a tetrazonium salt of 3,3′-dichlorobenzidine and acetoacetic acid-o-toluidide to form C.I. I. Sorbitan fatty acid ester or polyoxyethylene containing 2 to 5 hydroxyl groups at any stage prior to filtration in a method for producing a disazo pigment composition for water-based inks or water-based paints that is Pigment Yellow 14, heat-aged and filtered and washed A disazo pigment composition for water-based inks or water-based paints having a pH value of 8 to 11 according to JIS K 5101-17-1, characterized by containing a sorbitan fatty acid ester and carrying out heat aging with alkalinity. Production method. The sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups is a polyoxyethylene sorbitan fatty acid ester of HLB 13-17, The production of a disazo pigment composition for water-based inks or water-based paints according to claim 3 Method. The tetrazonium salt of 3,3'-dichlorobenzidine and acetoacetic acid-o-toluidide are coupled in the presence of sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester containing 2 to 5 hydroxyl groups. 5. A process for producing a disazo pigment composition for water-based ink or water-based paint as described in 4. Claims for coupling by adding a tetrazonium salt of 3,3′-dichlorobenzidine and acetoacetic acid-o-toluidide in water containing 2-5 hydroxyl groups and containing sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester Item 6. A process for producing a disazo pigment composition for water-based ink or water-based paint according to Item 5.