JPH0235786B2 - GANRYOSOSEIBUTSU - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a pigment composition that is suitable for use, particularly excellent in non-aggregation and non-crystallinity. In general, practically useful pigments that exhibit vivid color tones and high tinting power in various coating compositions are composed of fine particles. However, fine particles of pigments make it difficult to obtain stable dispersions when dispersed in non-aqueous vehicles such as offset inks, gravure inks and paints, which has an important impact on manufacturing operations and the value of the resulting products. This often results in a variety of problems that can cause problems. For example, dispersions containing pigments made up of fine particles often have a high viscosity, making it difficult to remove the product from the dispersion machine and transport it, and even worse, gelation during storage, making it difficult to use. It may become. Furthermore, when different types of pigments are mixed and used, phenomena such as color separation due to aggregation and sedimentation may result in color unevenness and a significant decrease in coloring power in the developed product. Furthermore, the surface of the paint film of the developed product may suffer from poor conditions such as reduced gloss and poor leveling. Further, although not directly related to pigment dispersion, some organic pigments experience a phenomenon that involves a change in the crystalline state of the pigment. In other words, the pigment crystal particles, which are energetically unstable in non-aqueous vehicles such as offset inks, gravure inks, and paints, change their size and morphology and shift to a stable state, resulting in a significant change in hue in the color spread. Product value may be impaired due to changes in color, decrease in coloring power, generation of coarse particles, etc. The present inventors have developed an offset ink as described above,
We have conducted studies to solve various problems that occur in non-aqueous vehicles such as gravure inks and paints, and have invented a method for producing pigment compositions that is excellent in practice. That is, the present invention comprises 100 parts by weight of a pigment, 0.5 to 40 parts by weight of an aluminum salt of benzoic acid or its derivative, and 0.5 to 40 parts by weight of a compound represented by the following general formula ().
30 parts by weight of the pigment composition. General formula () (Symbols in the formula are the same as above) In order to improve the non-aggregation property and crystal stability of pigments, many proposals have been made so far, centering on copper phthalocyanine-based and quinacridone-based pigments. This content can be broadly divided into the following two categories based on technical methods. The first method, as seen in USP 3,370,971 and USP 2,965,511, involves coating the surface of pigment particles with a colorless compound such as siliceous oxide, aluminum oxide, and tertiary butylbenzoic acid. The second method, as typified by Japanese Patent Publication No. 41-2466, is obtained by using an organic pigment as a base core and introducing substituents such as a sulfon group, sulfonamide group, aminomethyl group, or phthalimidomethyl group into the side chain. This is a method of mixing compounds. Compared to the first method, the second method has a significantly greater effect on pigment non-aggregation, crystal stability, etc. in a non-aqueous vehicle, and is also very advantageous judging from the ease of manufacturing the pigment composition. This is a great method. However, in the second method, since the compound added is derived from a compound having the same chemical structure as the pigment, it has strong inherent coloring, and is subject to significant limitations when used with pigments of different hues. Therefore, it is necessary to prepare corresponding compounds for each individual pigment, which is extremely disadvantageous in the production of pigment compositions. Although the present invention uses a method classified as the second method, both the aluminum salt of benzoic acid or its derivative and the compound represented by the general formula () are colorless or slightly colored. It is a chemical compound that can be arbitrarily mixed with pigments of various hues without causing any problem in hue. Therefore, this method is extremely advantageous in the production of pigment compositions, and it is a method for producing pigment compositions in a non-aqueous vehicle. Significant effects on non-aggregation, crystal stability, etc. can be obtained. Pigments used in the present invention include soluble and insoluble azo pigments, condensed azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, perylene/perinone pigments, dioxazine pigments, vat dye pigments, and base pigments. Organic pigments such as color dye pigments and inorganic pigments such as carbon black, titanium oxide, yellow lead, cadmium yellow, cadmium red, red, iron black, zinc white, deep blue, and ultramarine blue can be used. It is appropriate to use 0.5 to 40 parts by weight of benzoic acid or a derivative thereof according to the present invention per 100 parts by weight of the pigment, and to use 0.5 to 30 parts by weight of the compound represented by the general formula () per 100 parts by weight of the pigment. be. If less than these parts by weight are added, pigment non-aggregation,
No effect on crystal stability can be obtained, and addition of a large amount has an adverse effect on water resistance and solvent resistance. In addition, the above-mentioned benzoic acid or its derivatives include benzoic acid, nitrobenzoic acid, aminobenzoic acid, salicylic acid, aminosalicylic acid, terephthalic acid, isophthalic acid, phthalic acid, trimellitic acid,
Examples include pyromellitic acid. According to the research of the present inventors, in the above organic compound and the compound represented by the general formula (),
Salts made from other metals, such as calcium, zinc, barium, etc., instead of aluminum are significantly less effective than aluminum salts. As a method for preparing the pigment composition according to the present invention, the desired effect can be sufficiently obtained by simply mixing the pigment powder, the aluminum salt powder of benzoic acid or its derivative, and the powder of the compound represented by the general formula (). , mixed mechanically using a kneader, roll, attritor, super mill, various types of grinders, etc., or
A solution containing the above organic compound and the compound represented by the general formula (2) is added to a suspension system of pigment in water or an organic solvent and mixed, or a suspension system of benzoic acid or its derivatives is added to a suspension system of pigment in water or an organic solvent. Even better results can be obtained when a pigment composition is prepared by adding a solution or suspension of an alkali metal salt such as a sodium salt or a potassium salt, and further adding an aluminum salt such as aluminum chloride or aluminum sulfate. can. Alternatively, they may be mixed in the manufacturing process of printing ink or paint. The pigment composition thus obtained can be used in offset ink vehicles such as various rosin-modified resins, gravure inks such as lime rosin varnish, polyamide resin varnish, or vinyl chloride resin varnish, or when used in gravure inks such as nitrocellulose lacquer, amino alkyd varnish, etc. Resin air-drying or baking paint, acrylic lacquer, amino acrylic resin baking paint,
When used in urethane resin paints, etc., it exhibits good fluidity, such as lower viscosity of the dispersion and lower structural viscosity, compared to when pigments are used alone, and at the same time, problems such as color separation and crystal changes are also avoided. Therefore, it is possible to obtain a beautiful product with good gloss of the printed matter or coating film. The compound represented by the general formula () can be obtained as an industrial intermediate or product by a conventional method in the field of dyes, drugs, and other organic synthetic chemistry.The typical structure is shown below, and its effects are demonstrated in examples. , will be specifically explained using a comparative example. Γ Comparative Examples and Examples 1 to 16 Gravure Ink Test Gravure vinyl chloride resin varnish containing various pigments alone (comparative examples) or various pigments, various compounds shown in Table 1, and aluminum salts of benzoic acid or its derivatives. A gravure ink was prepared by blending the mixture so that the pigment content was 10% by weight or 25% by weight (for inorganic pigments), and its viscosity was examined. The results are shown in Table 2, and the material according to the present invention has excellent fluidity. In addition, the color tone of printed matter printed with this gravure ink

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[Table] Excellent results were also obtained in terms of clarity, coloring power, and gloss. Γ Comparative Examples and Examples 17 to 36 Paint Test Various pigments alone (comparative examples) or various pigments in amide alkyd resin varnish for baking paints, Table 1
A mixture of the various compounds shown above and an aluminum salt of benzoic acid or its derivatives is blended so that the pigment content is 6% by weight or 25% by weight (in the case of inorganic pigments) to prepare a paint and adjust its viscosity. Examined. The results are shown in Table 3, and the one according to the present invention has excellent fluidity. Furthermore, the storage stability of the paint was excellent, with little change in viscosity. Furthermore, the coating film had excellent color beauty, high tinting power, and gloss. In addition, with regard to dispersion stability, we will compare examples with respect to color separation stability, which is a particular problem in applications. The paints shown in the examples in Table 3 are cut with a titanium oxide base paint prepared in advance with aminoalkyd varnish so that the ratio of pigment to titanium oxide is 1/10 to obtain a light-colored paint. The light-colored paint was further diluted with xylene, adjusted to 20 seconds (25°C) in a food cup No. 4, and injected into a test tube. Table 4 shows the results of observing changes in the glass wall surface. Furthermore, Table 4 also shows the results of a comparative example (Zn) in which zinc salt was used instead of aluminum salt in Example 30.

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[Table] In all cases, the products according to the present invention show excellent results.

Claims (1)

[Scope of Claims] 1. A pigment composition comprising 100 parts by weight of a pigment, 0.5 to 40 parts by weight of an aluminum salt of benzoic acid or its derivative, and 0.5 to 30 parts by weight of a compound represented by the following general formula (). thing. General formula () (In the formula, A represents -CO-, -NH-, and B represents -CO-, -NH-, -S- or -O-. X is a halogen atom, a nitro group, a methoxy group, a methyl group, Represents a phenoxy group or phenylcarbamoyl group. Y is a direct bond, -NHCO-, or -
Represents a divalent bonding group consisting of a combination of NHCO- and a saturated or unsaturated alkylene group having 1 to 20 carbon atoms. Z represents a direct bond when Y is a direct bond,
When Y is a divalent bonding group, it represents a phenylene group. m represents an integer of 0 to 2, and n represents an integer of 1 to 2. )