JP2019189705A - Compound adhered aluminum pigment - Google Patents

Abstract

To provide an aluminum pigment, which can form a metallic coated film excellent in initial adhesiveness, excellent in metallic sheen or designability, and excellent in concealment property to a base material, and has high storage stability.SOLUTION: There is provided a compound adhered aluminum pigment containing (A) a compound having 2 or more carboxyl group, a (C) compound consisting of (B) a zirconium compound, and a flaky aluminum powder, in which 0.1 to 10 pts.mass of the (C) compound based on 100 pts.mass of the flaky aluminum powder is adhered to a surface of the flaky aluminum powder.SELECTED DRAWING: None

Description

  The present invention relates to a compound-attached aluminum pigment, and a paint and ink containing the compound-attached aluminum pigment.

Conventionally, aluminum pigments have been used for metallic paints, printing inks, plastics kneading, and the like for the purpose of obtaining a cosmetic effect that emphasizes a metallic feeling.
However, an aluminum pigment that has not been subjected to any surface treatment has a high metallic feel and design, but has a low adhesion to the resin when forming a coating film depending on the resin system used in paints and printing inks. For example, when an adhesion test by cellophane tape peeling is performed, there is a drawback that a large amount peels off.

As a method for improving the adhesion of the aluminum pigment as described above, a method of applying a predetermined surface treatment to the aluminum pigment has been proposed.
For example, Patent Documents 1 and 2 describe metallic coating films that are excellent in adhesion to resins when used as pigments for paints and printing inks while maintaining the excellent metallic luster and design of aluminum pigments. An aluminum pigment capable of providing the same and a method for producing the same are disclosed.

JP 2002-226733 A Japanese Patent Laying-Open No. 2015-172162

  However, in recent years, the demand for aluminum pigments has further increased. For example, in printing ink applications, it is required to increase the printing speed in order to improve productivity. In order not to occur, improvement of adhesion (initial adhesion) before the ink is completely dried has been a problem. Furthermore, in addition to having excellent design properties, adhesion to resins, and excellent concealment with respect to the base, it is also required to have high storage stability that is hardly affected by outside air temperature.

  Therefore, in the present invention, in view of the above-described problems of the prior art, it is possible to form a metallic coating film that is excellent in initial adhesion, excellent in metallic luster and design properties, and excellent in concealment with respect to the base, An object is to provide an aluminum pigment having high storage stability.

As a result of intensive studies to solve the above problems, the present inventors have (A) a compound (C) comprising two or more carboxyl groups, (B) a zirconium compound, flaky aluminum powder, The compound (C) is attached to the flaky aluminum powder, and the compound-attached aluminum pigment has excellent initial adhesion and design, excellent adhesion with the resin, and excellent adhesion to the ground. The present inventors have found that it is possible to exhibit concealability and an excellent effect on storage stability, and have completed the present invention.
That is, the present invention is as follows.

[1]
(A) a compound having two or more carboxyl groups and (B) a compound comprising (C) a zirconium compound,
Flaky aluminum powder,
Containing
A compound-attached aluminum pigment, wherein 0.1 to 10 parts by mass of the compound (C) is attached to the surface of the flaky aluminum powder with respect to 100 parts by mass of the flaky aluminum powder.
[2]
(A) The compound having two or more carboxyl groups is a polymerized carboxylic acid obtained by polymerizing soybean oil fatty acid or linseed oil fatty acid and acrylic acid, or a polymerized carboxylic acid obtained by polymerizing soybean oil fatty acid or linseed oil fatty acid. The compound-attached aluminum pigment according to [1].
[3]
The compound-attached aluminum pigment according to [1] or [2], wherein the (B) zirconium compound is zirconium acetate, zirconium propionate, or zirconium phosphate.
[4]
When the compound-attached aluminum pigment is heat-treated at 50 ° C. for 135 days, an average particle diameter difference Δd50 between the compound-attached aluminum pigment subjected to the heat treatment and the compound-attached aluminum pigment not subjected to the heat treatment is 1 The compound-attached aluminum pigment according to any one of [1] to [3], which is less than 0.0 μm.
[5]
A paint containing the compound-attached aluminum pigment according to any one of [1] to [4].
[6]
An ink containing the compound-attached aluminum pigment according to any one of [1] to [4].
[7]
The step of kneading the flaky aluminum powder and (A) the compound having two or more carboxyl groups, the kneaded product obtained in the kneading step is dispersed in an organic solvent, and (B) a zirconium compound is added thereto. A method for producing the compound-attached aluminum pigment according to any one of [1] to [4].

  According to the present invention, there is provided a compound-attached aluminum pigment having high storage stability that is excellent in initial adhesion, excellent in metallic luster and design properties, and capable of forming a metallic coating film that is also excellent in concealment with respect to a base. can get.

  Hereinafter, a mode for carrying out the present invention (hereinafter referred to as “the present embodiment”) will be described in detail. The following embodiments are examples for explaining the present invention, and are not intended to limit the present invention to the following contents. The present invention can be appropriately modified within the scope of the gist.

[Compound-attached aluminum pigment]
The compound-attached aluminum pigment of this embodiment is
(A) a compound having two or more carboxyl groups and (B) a compound comprising (C) a zirconium compound,
Flaky aluminum powder,
Containing
0.1 to 10 parts by mass of the (C) compound is attached to the surface of the flaky aluminum powder with respect to 100 parts by mass of the flaky aluminum powder.

As described above, the compound-attached aluminum pigment of this embodiment contains (A) a compound (C) composed of a compound having two or more carboxyl groups and (B) a zirconium compound, and flaky aluminum powder. . And the (C) compound has adhered to the surface of flaky aluminum powder.
The compound (C) adhering to the flaky aluminum powder does not simply mean that the flaky aluminum powder and the compound are mixed, but there is an interaction between the “flaky aluminum powder” and the “compound”. It means a certain state.
Examples of the interaction include a chemical bond, a hydrogen bond, an ionic bond, and a van der Waals force.

(Flake aluminum powder)
As the flaky aluminum powder used for the compound-attached aluminum pigment of the present embodiment, those having surface properties, particle sizes, and shapes required for metallic pigments such as surface gloss, whiteness, and glitter are suitable.
The shape may be various shapes such as a granular shape, a plate shape, a lump shape, and a scaly shape, but a scaly shape is preferable in order to give an excellent metallic feeling and luminance to the coating film.
The flaky aluminum powder has a thickness in the range of 0.001 to 1 μm, and preferably has a length or width in the range of 1 to 100 μm.
The aspect ratio of the flaky aluminum powder is preferably in the range of 10 to 20000.
Here, the aspect ratio is a value obtained by dividing the average major axis of the flaky aluminum powder by the average thickness of the flaky aluminum powder.
In addition, the purity of the flaky aluminum powder is not particularly limited, but it is preferable that the purity of the flaky aluminum powder is 99.5% or more.
The flaky aluminum powder can be obtained by a known method, for example, a production method described in WO99 / 54074, but is usually commercially available in a paste state, and this can also be used.

((A) Compound having two or more carboxyl groups)
The compound defined by (A) (also referred to as “(A) compound” in the present application) is a compound having two or more carboxyl groups, and is essentially an acid.
The compound (A) is not particularly limited, and conventionally known compounds can be used.
As said (A) compound, as long as it is a compound which has a 2 or more carboxyl group, the upper limit of the number of carboxyl groups in 1 molecule can be used, without specifically limiting.

  As the compound (A), a carboxylic acid having two or more carboxyl groups is preferable, and a carboxylic acid having at least two or more carboxyl groups and one or more double bonds, or a polymer thereof, or a dibasic acid is used. More preferred.

As the polymer, a polymer of an unsaturated carboxylic acid is preferable, and a thermal polymerization carboxylic acid is particularly preferable.
The thermal polymerization carboxylic acid is a carboxylic acid having two or more carboxyl groups and one or more double bonds obtained by thermal polymerization of one or more carboxylic acids having a double bond.

  Examples of starting materials for the unsaturated carboxylic acid polymer include oleic acid, acrylic acid, methacrylic acid, elaidic acid, linoleic acid, linolenic acid, and 3-octenoic acid, which are compounds having a carboxyl group and a double bond. Examples thereof include 10-undecenoic acid and fatty acid mixtures such as soybean oil fatty acid, linseed oil fatty acid, palm oil fatty acid, tall oil fatty acid and the like. The said starting material may be used individually by 1 type, and may use 2 or more types together.

  Preferred examples of the unsaturated carboxylic acid polymer include polymerized carboxylic acid obtained by polymerizing tall oil fatty acid, polymerized carboxylic acid obtained by polymerizing soybean oil or linseed oil fatty acid, soybean oil fatty acid or linseed oil fatty acid and acrylic acid. And polymerized carboxylic acid. Particularly preferred examples include polymerized carboxylic acid obtained by polymerizing soybean oil fatty acid or linseed oil fatty acid and acrylic acid, or polymerized carboxylic acid obtained by polymerizing soybean oil fatty acid or linseed oil fatty acid.

  Examples of commercial products (trade names) of the above polymerized carboxylic acids include Unidim 27, Enpole 1008, Prepol 1017, Versadim 216, Diacid 1550, Halidimer 300, Halidimer 200, and the like.

  Examples of the dibasic acid include, but are not limited to, for example, dialkoxycarbonylisodocosadiene diacid, isdocosadiene diacid, isodocosane diacid, isoeicosadiene diacid, butyloctane diacid, dimethyl Eicosane diacid, ethyl octadecanedioic acid, eicosadioic acid, eicosadiene diacid, acetone dicarboxylic acid, dodecanedioic acid, terephthalic acid, phthalic acid, isophthalic acid, decanedioic acid, nonanedioic acid, octanedioic acid, heptanedioic acid And at least one dibasic acid selected from the group consisting of hexanedioic acid.

((B) zirconium compound)
The zirconium compound defined in (B) (also referred to as “(B) zirconium compound” in the present application) is not particularly limited, and conventionally known compounds can be used.
(B) Examples of zirconium compounds include ammonium zirconium carbonate, zirconium orthosulfate, zirconium nitrate, zirconium sulfate, zirconium acetate, zirconium propionate, basic zirconium carbonate, zirconium zirconium chloride, zirconium oxychloride, zirconium phosphate, phosphoric acid. Examples include sodium zirconium, potassium zirconium carbonate, hydrofluoric zirconate, and ammonium zirconate fluoride. In particular, in view of the object of the present invention, zirconium acetate, zirconium propionate, or zirconium phosphate is preferable.
(B) A zirconium compound may be used individually by 1 type, and may use 2 or more types together.

The compound-attached aluminum pigment of the present embodiment is composed of the compound (A) and the zirconium compound (B) at a ratio of 0.1 to 10 parts by mass with respect to 100 parts by mass of the flaky aluminum powder described above (C ) Contains a compound. And the (C) compound has adhered to the surface of flaky aluminum powder.
(C) Content of a compound shall be 0.1 mass part or more from a viewpoint of adhesiveness etc. (especially adhesiveness), and shall be 10 mass parts or less from a viewpoint of glossiness, designability, etc. (especially glossiness and designability). It is preferable that it is 0.5-6 mass parts with respect to 100 mass parts of flaky aluminum powder from a viewpoint of the more outstanding storage stability.

[Method for producing compound-attached aluminum pigment]
The compound-attached aluminum metal pigment of this embodiment kneads flaky aluminum powder and (A) a compound having two or more carboxyl groups, and then disperses the kneaded product obtained in the kneading step in an organic solvent. It can be produced by adding a zirconium compound (B) thereto and reacting with the compound (A) adhered to the surface of the flaky aluminum powder.

  The kneading time is not particularly limited, but it is preferably within the range of 15 minutes to 3 hours, and more preferably within 15 minutes to 2 hours. If less than 15 minutes, the adhesion of the compound (A) is not sufficient, and the adhesion of the resulting compound-attached aluminum pigment may decrease. Since there is no change, productivity may decrease. Further, if the kneading time is made longer than necessary, the modification of the state of the compound-attached aluminum pigment may occur and the designability may be lowered.

  The temperature in the kneading step is not particularly limited, but is preferably in the range of 5 ° C to 80 ° C. If the temperature is less than 5 ° C, the compound (A) may not adhere sufficiently, and if the temperature exceeds 80 ° C, the adhesion of the compound (A) does not change, which may lead to energy loss.

  The organic solvent may be inert to the flaky aluminum powder, and is not limited to the following, for example, aliphatic hydrocarbons such as hexane, heptane, octane, mineral spirits; benzene, toluene, Aromatic hydrocarbons such as xylene and solvent naphtha; ethers such as tetrahydrofuran and diethyl ether; alcohols such as ethanol, 2-propanol and butanol; esters such as ethyl acetate and butyl acetate; cellosolve such as ethylene glycol monoethyl ether Kind.

The mass concentration of the flaky aluminum powder containing the compound (A) in the organic solvent is preferably 0.1 to 40% by mass, more preferably 1 to 35% by mass.
From the viewpoint of the reaction rate between the (A) compound and the (B) zirconium compound, 0.1% by mass or more is preferable, and from the viewpoint of dispersibility, 40% by mass or less is preferable.

  The temperature at which the (B) zirconium compound is added is not particularly limited as long as the reaction between the (A) compound and the (B) zirconium compound occurs, but is preferably 60 ° C. or higher and 150 ° C. or lower. Moreover, it is preferable to add and react in an inert gas atmosphere such as nitrogen or helium in order to increase the reaction efficiency.

Moreover, when making a (A) compound and a (B) zirconium compound react, a solvent can also be added or substituted as needed.
As the organic solvent, an ester-based solvent is preferable from the viewpoint of environmental load and drying property.
In particular, when propyl acetate is used, the amount of residual solvent is small even when the drying temperature is low, which is preferable from the viewpoint of adhesion and odor.
The particle diameter of the flaky aluminum powder is increased by the adhesion of the compound (C) composed of the compound (A) and the zirconium compound (B). The difference in average particle diameter before and after adhesion is preferably 1.5 μm or less, more preferably 1.1 μm or less, from the viewpoint of concealment of the aluminum pigment of this embodiment with respect to the base.

[Usage mode of compound-attached aluminum pigment]
The compound-attached aluminum pigment of this embodiment can be used as a pigment for paints and inks. As the paint or ink, either a solvent type or an aqueous type can be used.
When the compound-attached aluminum pigment of this embodiment is used in a solvent-type paint and ink, the paint resin or ink resin used in conventional metallic paints and metallic inks is used as the paint resin or ink resin. be able to.
The resin for paint or ink is not limited to the following, but for example, acrylic resin, alkyd resin, oil-free alkyd resin, vinyl chloride resin, urethane resin, melamine resin, unsaturated polyester resin, urea resin , Cellulose resin, epoxy resin, fluororesin and the like.
These may be used alone or in combination of two or more.

  When the compound-attached aluminum pigment of the present embodiment is used as a solvent-based paint and ink pigment, the amount of the aluminum pigment used is 0.1 to 300 parts by mass with respect to 100 parts by mass of the resin for paint or ink. Is preferable, and 0.2-200 mass parts is more preferable. 0.1 mass parts or more is preferable from the viewpoint of metallic gloss, and 300 mass parts or less is preferable from the viewpoint of physical properties of the coating film.

Solvent-type paints and ink diluents are not limited to the following, but include, for example, aromatic compounds such as toluene and xylene; aliphatic compounds such as hexane, heptane, and octane; ethanol, butanol, etc. Examples include alcohols; esters such as ethyl acetate and butyl acetate; ketones such as methyl ethyl ketone; chlorine compounds such as trichloroethylene; and cellosolves such as ethylene glycol monoethyl ether. These diluents may be used alone or in a combination of two or more.
The composition of the diluent may be appropriately determined in consideration of solubility in paint and ink resins, coating film formation characteristics, coating workability, and the like.

  In addition, for paints and inks, pigments, dyes, wetting agents, dispersants, anti-splitting agents, leveling agents, slip agents, anti-skinning agents, anti-gelling agents, antifoaming agents commonly used in the paint industry An additive such as an agent may be further added.

The paint and ink can also be used as a water-based paint by using a water-based paint resin.
However, when an aluminum pigment is used, it may react with water in water-based paints and inks. In such a case, it is necessary to add a reaction inhibitor.
Here, the resin for water-based paints is a water-soluble resin or a water-dispersible resin, and may be used alone or in a mixture of two or more. The type may be appropriately selected depending on the purpose and application, and is not particularly limited. However, for coating materials, generally used are water-based coating resins such as acrylic, acrylic-melamine, polyester, and polyurethane. Of these, acrylic-melamine is preferred because it is most widely used.

  When used as a water-based paint or ink, the amount of the aluminum pigment used in the present embodiment is preferably 0.1 to 300 parts by weight, and 0.2 parts by weight with respect to 100 parts by weight of the resin for water-based paints. It is more preferable that it is part-200 mass parts. From the viewpoint of obtaining metallic luster, it is preferably 0.1 parts by mass or more, and from the viewpoint of physical properties of the coating film, it is preferably 300 parts by mass or less.

  Examples of various additives include dispersants, thickeners, sagging inhibitors, antifungal agents, ultraviolet absorbers, film forming aids, surfactants, other organic solvents, water, etc. Any of those that can be generally used and that does not impair the effects of the present invention can be used, and it is preferably added in an amount that does not impair the effects of the present invention.

[Painting method]
As a coating method using a paint or ink containing the compound-attached aluminum group pigment of the present embodiment, a known method can be applied.
For example, spraying method, flow coating method, roll coating method, brush coating method, dip coating method, spin coating method, screen printing method, casting method, gravure printing method, flexographic printing method and the like can be mentioned.
Further, after coating, it is possible to carry out heat treatment at 20 to 500 ° C., more preferably 40 to 250 ° C., ultraviolet irradiation or the like, if desired. Moreover, it is also possible to apply | coat a coating material with respect to the base material heated to 40-250 degreeC.

[Use]
The compound-attached aluminum pigment of this embodiment can be used for painting for automobiles, general household appliances, information household appliances represented by mobile phones, or predetermined printing applications.
Specifically, for example, a base material made of a predetermined material such as a metal such as iron or magnesium alloy or plastic used for automobiles can be coated and printed, and high designability can be exhibited.

  Hereinafter, the present invention will be described in detail with reference to specific examples and comparative examples, but the present invention is not limited to the following examples.

In Examples and Comparative Examples, various physical properties were measured by the following methods.
[Method for measuring physical properties]
<1. Average particle diameter>
Manufactured by Shimadzu Corporation; using SALD-2200 (laser diffraction particle size distribution measuring device), a compound-attached aluminum pigment and paste containing flaky aluminum powder (manufactured by Asahi Kasei Corporation, manufactured by Examples and Comparative Examples described later) The average particle size of GX-4100) was measured.

<2. (C) Compound amount>
The amount of the compound (C) with respect to 100 parts by mass of the flaky aluminum powder is the compound (A) when the mass (2000 g × 0.74) of the non-volatile content of the aluminum paste used as the flaky aluminum powder component is 100 parts by mass. And (B) the mass part of the compound (C), which is the sum of the zirconium compounds, was calculated.

<3. Initial adhesion>
The metallic ink obtained in each Example and Comparative Example was applied to a PET film with a bar coater so as to have a dry film thickness of 2 μm to obtain a coating film.
A sample obtained by drying the obtained coating film at 50 ° C. for 2 hours was used as an evaluation sample.
Cellotape (registered trademark: manufactured by Nichiban Co., Ltd., width: 18 mm) was closely attached to the coating film, pulled at an angle of 90 °, and the degree of peeling of the aluminum pigment particles was visually observed and evaluated as follows.
◎: No peeling was observed. ○: Almost no peeling was observed. △: Some peeling was observed. ×: Remarkable peeling was observed.

<4. Concealment>
The metallic ink obtained in each Example and Comparative Example was applied to a PET film with a bar coater so as to have a dry film thickness of 2 μm to obtain a coating film.
A sample obtained by drying the obtained coating film at 50 ° C. for 24 hours was used as an evaluation sample. Using a haze meter HZ-V3 manufactured by Suga Test Instruments Co., Ltd., the total light transmittance (Tt) was evaluated.
The smaller the value, the better the concealment.

<5. Metal gloss>
<3. A coating film prepared in the same manner as the dry coating film used for evaluation under the concealing property was used for evaluation.
A 60 degree gloss (both incident angle and reflection angle is 60 degrees) is measured using a gloss meter (manufactured by Suga Test Instruments Co., Ltd., digital variable gloss meter UGV-5D). G 'is a measured value of 60 ° gloss of a coated plate using the metal pigment of the present invention, and G is a measured value of 60 ° gloss of a coated plate similarly produced using a metal pigment not coated with a resin. R was determined by the following equation.
R = (G ′ / G) × 100
Depending on the value of the gloss retention rate R, the evaluation was as follows.
The larger the numerical value, the better the metallic luster. From a practical point of view, it was judged that it was good if it was 80 or more and excellent if it was 90 or more.
◎ (excellent): 90 or more ○ (good): less than 90 to 80 or more Δ (possible): less than 80 to 70 or more × (impossible): less than 70 <6. Storage stability>
The compound-attached aluminum pigment produced according to Examples and Comparative Examples described later was heat-treated at 50 ° C. The storage stability was evaluated as follows based on the degree of increase in average particle size (aggregation degree) before and after heat treatment.
The smaller the Δd50 value, the better the storage stability. From a practical point of view, it can be used without any particular problem if it is kept at 1.5 μm or less after 135 days of heat treatment at 50 ° C. Judged to be good if kept.
○ (Good): 135 days at 50 ° C., Δd50 ≦ 1.0 μm
Δ (possible): 135 days at 50 ° C., 1.0 μm <Δd50 ≦ 1.5 μm
× (Not possible): 135 days at 50 ° C., Δd50> 1.5 μm

[Example 1]
In an 8 L kneader, 2000 g of a commercially available paste containing flaky aluminum powder (manufactured by Asahi Kasei Co., Ltd., GX-4100 “average particle size 10 μm, nonvolatile content 74 mass%”), and (A) soybean oil fatty acid and acrylic acid as compounds Was charged with 14.8 g of a carboxylic acid having a double bond (trade name: Diacid 1550). And nitrogen gas was introduce | transduced and the temperature in a system was heated up at 40 degreeC. Subsequently, it knead | mixed for 30 minutes at 40 degreeC.
Next, 6810 g of the recovered kneaded material and mineral spirit were charged into a 20 L reactor. The mixture was stirred while introducing nitrogen gas, and the system temperature was raised to 70 ° C. Next, (B) 7.4 g of zirconium phosphate as a zirconium compound, and a mixed liquid consisting of 37.0 g of isopropanol and 1755 g of mineral spirit were added at a rate of about 10 g / min by a metering pump. The mixture was finally stirred for a total of 6 hours while maintaining at 70 ° C.
After completion of the reaction for 6 hours, the mixture was naturally cooled and the slurry was filtered to obtain a compound-attached aluminum paste (aluminum pigment).
The non-volatile content of the aluminum pigment according to JIS-K-5910 was 50% by mass.
The difference between the average particle size before and after the reaction, that is, the average particle size of the aluminum pigment, and the average particle size of the commercially available paste containing flaky aluminum powder was 0.5 μm.
To 6 g of the obtained aluminum pigment, 10 g of a polyurethane resin (Samprene IB-1700D (manufactured by Sanyo Chemical Industries)), 4 g of ethyl acetate, 4 g of methyl ethyl ketone, and 4 g of isopropanol are added, and stirred with a magnetic stirrer for 10 minutes. Got.
Using the obtained metallic ink, the initial adhesion of the coating film, the concealing property of the coating film, and the metallic gloss were evaluated. The evaluation results are shown in Table 1 below along with the storage stability evaluation results.

[Examples 2 to 5], [Comparative Examples 1 to 3]
A composition-attached aluminum pigment and paint were produced in the same manner as in Example 1 except that the composition of Example 1 was changed, and the same characteristics evaluation as in Example 1 was performed. Table 1 shows the compositions of Examples 2 to 5 and Comparative Examples 1 to 3 and the evaluation results thereof.

  In Examples 1 to 5, excellent initial adhesion, metallic luster, high concealability, and excellent storage stability can be obtained, and excellent design can be obtained in view of these results. I understood.

  The compound-attached aluminum pigment of the present invention is used for paints and printing inks for information home appliances such as automobiles, general home appliances, and mobile phones, specifically, metals such as iron and magnesium alloys, or plastics. It has industrial applicability in paint and ink applications for such substrates.

Claims (7)

(A) a compound having two or more carboxyl groups and (B) a compound comprising (C) a zirconium compound,
Flaky aluminum powder,
Containing
A compound-attached aluminum pigment, wherein 0.1 to 10 parts by mass of the compound (C) is attached to the surface of the flaky aluminum powder with respect to 100 parts by mass of the flaky aluminum powder.   (A) The compound having two or more carboxyl groups is a polymerized carboxylic acid obtained by polymerizing soybean oil fatty acid or linseed oil fatty acid and acrylic acid, or a polymerized carboxylic acid obtained by polymerizing soybean oil fatty acid or linseed oil fatty acid. The compound-attached aluminum pigment according to claim 1.   The compound-attached aluminum pigment according to claim 1 or 2, wherein the (B) zirconium compound is zirconium acetate, zirconium propionate, or zirconium phosphate.   When the compound-attached aluminum pigment is heat-treated at 50 ° C. for 135 days, an average particle diameter difference Δd50 between the compound-attached aluminum pigment subjected to the heat treatment and the compound-attached aluminum pigment not subjected to the heat treatment is 1 The compound-attached aluminum pigment according to any one of claims 1 to 3, which is less than 0.0 µm.   The coating material containing the compound adhesion aluminum pigment as described in any one of Claims 1 thru | or 4.   The ink containing the compound adhesion aluminum pigment as described in any one of Claims 1 thru | or 4.   The step of kneading the flaky aluminum powder and (A) the compound having two or more carboxyl groups, the kneaded product obtained in the kneading step is dispersed in an organic solvent, and (B) a zirconium compound is added thereto. The method of manufacturing the compound adhesion aluminum pigment as described in any one of Claims 1 thru | or 4 including a process.