Process for producing branched polyester and solvent type pigment dispersion composition and solvent type paint composition containing the branched polyester

Abstract

The present invention provides a solvent type pigment dispersion composition containing a resin having good compatibility with various pigment dispersion pastes and / or various resins, and further provides a high concentration solvent type pigment dispersion composition. A solvent type pigment dispersion composition containing a branched polyester (A) containing, as a constituent component, a component containing a polyol (a1) having 3 or more reactive functional groups, a dicarboxylic acid and / or a dicarboxylic anhydride (a2), and a mono-epoxide having a long chain hydrocarbon group (a3), a pigment dispersing resin (B), a pigment (C), and an organic solvent (D).

Description

Technical Field

[0001] This invention relates to a solvent-based pigment dispersion composition and a solvent-based coating composition. Background Technology

[0002] Typically, organic and / or inorganic pigments are widely used in coatings for purposes such as coloring, opacity, aesthetics, and rust prevention. These pigments are dispersed to form pigment dispersion compositions (also known as pigment dispersion pastes).

[0003] Prepare the pigment dispersion composition in the corresponding amount of color, mix it in a way that achieves the desired coloring, and further add resins, additives, etc. that correspond to the coating properties (purpose of use) to manufacture the final colored coating composition.

[0004] When mixing multiple pigment dispersion compositions, or when mixing resins and / or additives into a pigment dispersion composition, sometimes the pigment dispersion stability is insufficient and re-aggregates, or the flowability deteriorates, or the hue shift or gloss is insufficient when forming a coating film. To address these problems, various proposals have been made to date.

[0005] For example, patent documents 1 to 3 propose adding pigment derivatives with the same skeleton as the dispersed pigment during pigment dispersion, or using pigments treated with these pigment derivatives. However, the methods based on these proposals have the following drawbacks: not only is the pigment dispersion effect still insufficient, but also a variety of pigment derivatives are required, resulting in poor versatility, and the manufacturing process is expensive.

[0006] In addition, for example, Patent Document 4 proposes a polyester resin as a pigment dispersion resin, but its properties such as compatibility are not sufficient. The polyester resin is prepared from an acid component and an alcohol component, wherein the acid component contains a straight-chain acid having 12 or more carbon atoms in an amount of less than 25% by weight based on the total monomer content of the polyester resin.

[0007] Furthermore, anticipating that the required coating appearance will become increasingly diverse in the future, there will be a corresponding demand for pigment dispersion performance for various color materials.

[0008] Furthermore, in recent years, from the perspective of protecting the Earth's environment, the coatings industry urgently needs to reduce the amount of organic solvents in coatings and increase the solids content. As a method for increasing the solids content, research typically focuses on reducing the molecular weight of the resin used in coatings to lower viscosity. However, reducing the molecular weight of the resin can lead to problems such as decreased curing properties or reduced coating film performance.

[0009] In addition to reducing the molecular weight of the resin used in coatings, another method to achieve high solids content in coatings is to increase the pigment concentration (reducing the amount of resin used to disperse the same amount of pigment). However, when coatings are typically made to have high pigment concentration, the following problems arise: thickening of the pigment dispersion composition, aggregation of pigments in the pigment dispersion composition and / or coating, and poor letdown stability during coating, making it difficult to obtain a stable pigment dispersion composition and / or coating.

[0010] Existing technical documents

[0011] Patent documents

[0012] Patent Document 1: Japanese Patent Application Publication No. 59-96175

[0013] Patent Document 2: Japanese Patent Application Publication No. 02-36252

[0014] Patent Document 3: Japanese Patent Application Publication No. 10-81849

[0015] Patent Document 4: Japanese Patent Publication No. 8-507571 Summary of the Invention

[0016] The problem that the invention aims to solve

[0017] The problem to be solved by the present invention is to provide a solvent-based pigment dispersion composition comprising a resin that is compatible with various resins, and further to provide a high-concentration solvent-based pigment dispersion composition.

[0018] Solution for solving the problem

[0019] Under the aforementioned circumstances, the inventors conducted in-depth research and discovered that the above problems could be solved by using a solvent-based pigment dispersion composition containing a certain amount of branched polyester (A) with a specific structure. Furthermore, based on numerous repeated experiments, the inventors found that by using a branched polyester with a specific structure and characteristic values, a branched polyester resin with good compatibility (solubility) with solvents of lower polarity and with resins can be provided, thereby providing a solvent-based pigment dispersion composition with a higher concentration. This invention is based on the above-mentioned new insights.

[0020] Therefore, the present invention provides the following items.

[0021] Item 1. A solvent-based pigment dispersion composition comprising a branched polyester (A), a pigment dispersion resin (B), a pigment (C), and an organic solvent (D), wherein the branched polyester (A) comprises a component including: a polyol (a1) having three or more reactive functional groups, a dicarboxylic acid and / or a dicarboxylic anhydride (a2), and a monoepoxide compound (a3) ​​having a long-chain hydrocarbon group.

[0022] Item 2. The solvent-based pigment dispersion composition according to Item 1, wherein the branched polyester (A) further contains a chain extender (a4) as a constituent component.

[0023] Item 3. The solvent-based pigment dispersion composition according to Item 1 or 2, wherein the branched polyester (A) has an acid value of less than 10 mg KOH / g, a number-average molecular weight of 500 to 50,000, a hydroxyl value of 1 mg KOH / g to 200 mg KOH / g, and a degree of branching of 2.5 to 7.

[0024] Item 4. The solvent-based pigment dispersion composition according to any one of items 1 to 3, wherein the monoepoxide (a3) ​​is a monoepoxide having a hydrocarbon group having 6 or more carbon atoms.

[0025] Item 5. The solvent-based pigment dispersion composition according to any one of items 1 to 4, wherein, based on the solid content of the solvent-based pigment dispersion composition, it contains 5% to 70% by mass of branched polyester (A).

[0026] Item 6. The solvent-based pigment dispersion composition according to any one of items 1 to 5, wherein, based on the total mass of the solvent-based pigment dispersion composition, it contains 5% to 70% by mass of pigment (C).

[0027] Item 7. A solvent-based coating composition obtained by mixing multiple (multi-color) solvent-based pigment dispersion compositions as described in any one of Items 1 to 6.

[0028] Item 8. A method for manufacturing a solvent-based coating composition, wherein multiple (multi-color) solvent-based pigment dispersion compositions as described in any one of Items 1 to 6 are prepared, and the multiple solvent-based pigment dispersion compositions are added to the same coating container and mixed to adjust the color.

[0029] Item 9. A method for manufacturing a branched polyester, comprising the steps of sequentially performing the following steps:

[0030] Step 1-1: A step of reacting a polyol (a1) containing a reactive functional group with three or more functions and a dicarboxylic acid and / or a dicarboxylic anhydride (a2) to form an intermediate product.

[0031] Step 1-2: A step of reacting the components containing the intermediate product and the monoepoxide compound (a3) ​​having a long-chain hydrocarbon group.

[0032] Item 10. The method for manufacturing branched polyester according to Item 9, wherein, after steps 1-1 and 1-2, the method comprises:

[0033] Steps 1-3: Steps that further react the components containing the chain extender (a4).

[0034] Item 11. The method for manufacturing branched polyester according to Item 9, wherein the acid value of the polyol (a1) having 3 or more reactive functional groups is less than 10 mg KOH / g.

[0035] Item 12. A method for manufacturing a branched polyester, comprising the steps of performing the following steps:

[0036] Step 2-1: A step in which a component comprising a polyol (a1) having three or more reactive functional groups, a dicarboxylic acid and / or a dicarboxylic anhydride (a2), and a monoepoxide compound (a3) ​​having a long-chain hydrocarbon group reacts simultaneously.

[0037] Item 13. The method for manufacturing branched polyester according to Item 12, wherein, after step 2-1, the method comprises:

[0038] Step 2-2: A further reaction of the components containing the chain extender (a4).

[0039] Item 14. A method for manufacturing a branched polyester according to any one of items 9 to 13, wherein the acid value of the polyol (a1) having 3 or more reactive functional groups is less than 10 mg KOH / g.

[0040] Item 15. A method for manufacturing a solvent-based pigment dispersion composition, wherein a branched polyester (A), a pigment dispersion resin (B), a pigment (C), and an organic solvent (D) obtained by any one of items 9 to 14 are mixed, and then the pigment is dispersed using a medium to obtain the solvent-based pigment dispersion composition.

[0041] Item 16. The method for manufacturing the solvent-based pigment dispersion composition according to Item 15, wherein, based on the solid content of the solvent-based pigment dispersion composition, it contains 5% to 70% by mass of branched polyester (A).

[0042] Item 17. The method for manufacturing a solvent-based pigment dispersion composition according to Item 15, wherein, based on the total mass of the solvent-based pigment dispersion composition, it contains 5% to 70% by mass of pigment (C).

[0043] Invention Effects

[0044] According to the present invention, solvent-based pigment dispersion compositions and / or solvent-based coating compositions with excellent compatibility (including dispersion stability and storage stability) can be obtained. Furthermore, it is particularly possible to achieve high solids content (high concentration) in solvent-based pigment dispersion compositions and / or solvent-based coating compositions, resulting in coating films with excellent processability. Detailed Implementation

[0045] The present invention will now be described in detail.

[0046] It should be noted that the present invention is not limited to the following embodiments, and should be understood to include various variations implemented without changing the spirit of the present invention.

[0047] Solvent-based pigment dispersion compositions

[0048] In one embodiment, the present invention provides a solvent-based pigment dispersion composition comprising a branched polyester (A), a pigment dispersion resin (B), a pigment (C), and an organic solvent (D).

[0049] Branched polyester (A)

[0050] The branched polyester (A) contains components comprising: a polyol (a1) having three or more reactive functional groups, a dicarboxylic acid and / or a dicarboxylic anhydride (a2), and a monoepoxide compound (a3) ​​having a long-chain hydrocarbon group. In this invention, the branched polyester (A) containing components (a1), (a2), and (a3) ​​as components means that the branched polyester (A) is obtained by a method comprising: a step of (co)polymerizing raw materials containing components (a1), (a2), and (a3). Here, the "process of copolymerizing raw materials containing components (a1), (a2), and (a3)" includes not only a process of copolymerizing raw materials containing all of the above-mentioned components (a1), (a2), and (a3) ​​through a one-stage reaction, but also a process of performing the reaction in multiple stages, such as reacting a portion of the above-mentioned components (a1), (a2), and (a3) ​​first, and reacting the resulting reaction product with the remaining components.

[0051] Polyols with three or more reactive functional groups (a1)

[0052] The polyol (a1) having three or more reactive functional groups is a polyol having three or more reactive functional groups and two or more hydroxyl groups.

[0053] The aforementioned reactive functional groups specifically refer to functional groups selected from the group consisting of hydroxyl, carboxyl, amino, and thiol groups.

[0054] Of these, the most preferred component (a1) is a compound whose reactive functional groups are all hydroxyl groups and which has three or more hydroxyl groups (trifunctional).

[0055] Examples of polyols having trifunctional hydroxyl groups include glycerol, trimethylolpropane, trimethylolethane, trimethylolbutane, 3,5,5-trimethyl-2,2-dihydroxymethylhexane-1-ol, 1,2,6-hexanetriol, and triethyl isocyanurate, which can be used alone or in combination with two or more.

[0056] Polyols with 4 functional hydroxyl groups, such as erythritol, pentaerythritol, di(trimethylolpropane), diglycerol, and di(trimethylolethane), can be used alone or in combination with two or more.

[0057] Polyols with hydroxyl groups having five or more functions, such as pentaerythritol, tripentaerythritol, xylitol, and sorbitol, can be used alone or in combination with two or more.

[0058] Furthermore, examples of polyols having two or more hydroxyl groups and one or more carboxyl groups include dihydroxycarboxylic acids (e.g., dihydroxymethylacetic acid, dihydroxymethylbutyric acid, dihydroxymethylpropionic acid, dihydroxymethylbutyric acid, dihydroxymethylvaleric acid), trihydroxycarboxylic acids, and dihydroxydicarboxylic acids, which can be used alone or in combination with two or more.

[0059] Furthermore, as polyols having two or more hydroxyl groups and one or more amino groups, examples include dihydroxyamines (e.g., diethanolamine, dipropanolamine), which can be used alone or in combination with two or more.

[0060] From a reactivity point of view, polyols with trifunctional hydroxyl groups are preferred.

[0061] In addition, difunctional polyols and / or monofunctional alcohols can also be used as needed in combination with the above-mentioned polyols having three or more reactive functional groups (a1).

[0062] Examples of difunctional polyols include: ethylene glycol, propylene glycol, diethylene glycol, trimethylene glycol, tetraethylene glycol, triethylene glycol, dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 2,3-butanediol, 1,2-butanediol, 2-methyl-1,3-propanediol, 3-methyl-1,2-butanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,2-pentanediol, 1,5-pentanediol, 1,4-pentanediol, 2,4-pentanediol, 2,3-dimethyltrimethylenediol, tetraethylenediol, 3-methyl-4,3-pentanediol, and 3-methyl-1,5-pentanediol. Diols such as 2,2,4-trimethyl-1,3-pentanediol, 1,6-hexanediol, 1,5-hexanediol, 1,4-hexanediol, 2,5-hexanediol, neopentanediol, 1,4-cyclohexanediol, tricyclodecanediol, neopentanediol hydroxypentanoate, hydrogenated bisphenol A, hydrogenated bisphenol F, and dimethylolpropionic acid; polylactone diols formed by adding lactone compounds such as ε-caprolactone to these diols; ester diol compounds such as bis(hydroxyethyl) terephthalate; epoxide adducts of bisphenol A; and polyether diol compounds such as polyethylene glycol, polypropylene glycol, and polybutanediol, can be used alone or in combination with two or more.

[0063] As monofunctional alcohols, examples include methanol, ethanol, propanol, butanol, stearyl alcohol, 2-phenoxyethanol, etc., and one or more can be used alone or in combination.

[0064] As a component constituting the aforementioned branched polyester (A), from the perspective of achieving low branching, it is preferable to be substantially free of difunctional polyols and / or monofunctional alcohols, and particularly preferably, substantially free of monofunctional alcohols. "Substantially free" means, based on the content of polyols (a1) having three or more reactive functional groups, the content is preferably 10 mol% or less, more preferably 5 mol% or less, further preferably 1 mol% or less, and particularly preferably 0 mol%.

[0065] Dicarboxylic acids and / or dicarboxylic anhydrides (a2)

[0066] Examples of the dicarboxylic acids and / or dicarboxylic anhydrides (a2) mentioned above include: phthalic acid, isophthalic acid, terephthalic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, fumaric acid, itaconic acid, and other dicarboxylic acids, or their anhydrides, etc., which can be used alone or in combination with two or more. From the viewpoint of reactivity and the absence of condensation water formation in the reaction, dicarboxylic anhydrides are preferred. By suppressing condensation water, for example, when an isocyanate compound is used as a chain extender (a4), the reaction between condensation water and isocyanate can be suppressed, resulting in partial deactivation of the isocyanate groups, which is therefore preferred.

[0067] In addition, polycarboxylic acids with three or more functions and / or monofunctional carboxylic acids may also be used in combination with the above-mentioned dicarboxylic acids and / or dicarboxylic anhydrides (a2) as needed.

[0068] As polycarboxylic acids with three or more functions, examples include: trimellitic acid, pyromellitic acid, benzophenone tetracarboxylic acid, pyromellitic acid, ethylene glycol bis(dehydrated trimellitic acid ester), glyceryl tri(dehydrated trimellitic acid ester), 1,2,3,4-butanetetracarboxylic acid, 1,4,5,8-naphthalenetetracarboxylic acid, etc., and one or more can be used alone or in combination.

[0069] Examples of monofunctional carboxylic acids include acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, stearic acid, oleic acid, linoleic acid, cyclohexanecarboxylic acid, and benzoic acid. One or more of these can be used alone or in combination.

[0070] As a component constituting the aforementioned branched polyester (A), from the viewpoint of promoting the high molecular weight (hydrophobicity) of the branched portion, the monofunctional carboxylic acid is preferably present in small amounts. Preferably, based on the content of dicarboxylic acid and / or dicarboxylic anhydride (a2), the content of monofunctional carboxylic acid is preferably 50 mol% or less, more preferably 20 mol% or less, further preferably 10 mol% or less, and particularly preferably 0 mol%.

[0071] Furthermore, from the viewpoint of inhibiting gelation, it is preferable that the product is substantially free of polycarboxylic acids with more than three functions. "Substantially free" means, based on the content of dicarboxylic acids and / or dicarboxylic anhydrides (a2), preferably 10 mol% or less, more preferably 5 mol% or less, further preferably 1 mol% or less, and particularly preferably 0 mol%.

[0072] Monoepoxides with long-chain hydrocarbon groups (a3)

[0073] The aforementioned monoepoxide compounds (a3) ​​with long-chain hydrocarbon groups are monoepoxide compounds with hydrocarbon groups having 4 or more carbon atoms. They can hydrophobize branched polyesters (A) and improve their compatibility. Specifically, examples include: glycidyl trimethylacetate, glycidyl hexanoate, glycidyl cyclohexanecarboxylate, glycidyl 2-ethylhexanoate, glycidyl isononanoate, glycidyl decanoate, glycidyl undecanoate, glycidyl laurate, glycidyl myristate, glycidyl palmitate, glycidyl stearate, Cardura E10 (manufactured by Japan Epoxy Resin, neodecanoic acid monoglycidyl ester), etc.; glycidyl ethers such as butyl glycidyl ether, phenyl glycidyl ether, decyl glycidyl ether, etc.; and monoepoxides such as styrene oxide and AOEX24 (manufactured by Daicel Chemical Industries, a mixture of monoepoxide α-olefins), etc.

[0074] Furthermore, the aforementioned hydrocarbon groups with 4 or more carbon atoms may include, for example, hydrocarbon groups with substituents such as hydroxyl groups. Examples of such compounds include, for instance, 1,2-epoxyoctyl alcohol and hydroxyoctyl glycidyl ether.

[0075] The monoepoxide compound (a3) ​​having a long-chain hydrocarbon group can be used alone or in combination with two or more. From the viewpoint of compatibility, the lower limit for the number of carbon atoms is preferably 3 or more, more preferably 6 or more. As for the range of the number of carbon atoms in the monoepoxide compound (a3), for example, monoepoxide compounds having a hydrocarbon group having 3 or more and 30 or less carbon atoms are preferred, more preferably monoepoxide compounds having a hydrocarbon group having 6 or more and 30 or less carbon atoms, and even more preferably monoepoxide compounds having 8 or more and 20 or less carbon atoms.

[0076] Chain extender (a4)

[0077] The aforementioned branched polyester (A) may further contain a chain extender (a4) as part of its constituent components. As the chain extender (a4), any compound having reactive functional groups capable of linking the aforementioned branched polyester (A) to each other is preferred. To prevent gelation, it is preferable that the compound has two of these reactive functional groups. Specifically, chain extenders such as diisocyanate compounds, carbonate compounds such as diphenyl carbonate, and silicate compounds can be used. Diisocyanate compounds are preferred because they can improve physical properties by generating urethane bonds in the resin backbone.

[0078] As for the aforementioned diisocyanate compounds, any compound having two isocyanate groups can be used without restriction, including known compounds such as 2,4-toluene diisocyanate, mixtures of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate, diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, phenyl dimethyl diisocyanate, hydrogenated phenyl dimethyl diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and other known diisocyanates. One or more of these compounds can be used alone.

[0079] Specifically, examples of the aforementioned carbonate compounds include, for instance, diphenyl carbonate, dimethyl carbonate, bis(chlorophenyl) carbonate, m-toluene carbonate, dinaphthalene carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, ethylene carbonate, dipentyl carbonate, and dicyclohexyl carbonate. Furthermore, carbonate compounds comprising the same or different types of hydroxyl compounds derived from hydroxyl compounds such as phenols and alcohols can be listed, and one or more can be used alone or in combination.

[0080] Specifically, examples of the aforementioned silicate compounds include tetramethoxysilane, dimethoxydiphenylsilane, dimethoxydimethylsilane, diphenyldihydroxysilane, etc., and one or more of them can be used alone or in combination.

[0081] For the preferred embodiment of the manufacturing method of the above-mentioned branched polyester (A), in the following " Manufacturing of branched polyester (A) Construction method The details will be explained in the section on "".

[0082] Method for manufacturing branched polyester (A)

[0083] The branched polyester (A) obtained by the manufacturing method of the present invention contains components comprising the following substances as constituent components: a polyol (a1) having three or more reactive functional groups, a dicarboxylic acid and / or a dicarboxylic anhydride (a2), and a monoepoxide compound (a3) ​​having a long-chain hydrocarbon group, and further contains a chain extender (a4) as constituent components as needed.

[0084] In a preferred embodiment of the present invention, the following two methods (stage reaction and one-pot reaction) can be used as the manufacturing method of the above-mentioned branched polyester (A), and both are preferred to be used.

[0085] The first manufacturing method (stage reaction)

[0086] The first manufacturing method (stage reaction) is a method for manufacturing branched polyesters that includes the following steps performed sequentially:

[0087] Step 1-1: A step of reacting a polyol (a1) containing a reactive functional group with three or more functions and a dicarboxylic acid and / or a dicarboxylic anhydride (a2) to form an intermediate product.

[0088] Step 1-2: A step of reacting the components containing the intermediate product and the monoepoxide compound (a3) ​​having a long-chain hydrocarbon group.

[0089] Furthermore, it is preferable to include the following steps after the above-mentioned steps 1-1 and 1-2:

[0090] Steps 1-3: Steps that further react the components containing the chain extender (a4).

[0091] It should be noted that the manufacturing method of the present invention also includes adding other processes before, after and / or during the above-mentioned processes 1-1, 1-2 and processes 1-3, which may be applied as needed.

[0092] The second manufacturing method (one-pot reaction)

[0093] The second manufacturing method (one-pot reaction) is a method for manufacturing branched polyesters that includes the following steps:

[0094] Step 2-1: A step in which a component comprising a polyol (a1) having three or more reactive functional groups, a dicarboxylic acid and / or a dicarboxylic anhydride (a2), and a monoepoxide compound (a3) ​​having a long-chain hydrocarbon group reacts simultaneously.

[0095] Furthermore, it is preferable to include the following after step 2-1:

[0096] Step 2-2: A further reaction of the components containing the chain extender (a4).

[0097] It should be noted that the manufacturing method of the present invention also includes adding other processes before, after and / or during the above-mentioned process 2-1 and process 2-2, which may be applied as needed.

[0098] In this invention, any manufacturing method can be preferred, but from the viewpoints of saving processes and energy, suppressing the high molecular weight of resin, and suppressing condensation water, the second manufacturing method (one-pot reaction) can be preferred.

[0099] The synthesis conditions in the first and second methods described above are not particularly limited. For example, the synthesis can be carried out by heating at 90°C to 250°C for 5 to 10 hours in steps 1-1 to 1-2 and step 2-1, to conduct the esterification reaction (including transesterification) of hydroxyl and carboxyl groups and / or the esterification reaction of epoxy and carboxyl groups. As the catalyst at this time, known catalysts such as dibutyltin oxide, antimony trioxide, zinc acetate, manganese acetate, cobalt acetate, calcium acetate, lead acetate, tetrabutyl titanate, and tetraisopropyl titanate can be used.

[0100] In the reaction of the chain extender (a4) in steps 1-3 and 2-2 as needed (e.g., the carbamate reaction of hydroxyl groups with isocyanate groups), a catalyst known in itself (e.g., organotin catalyst, bismuth catalyst, lead catalyst, zinc catalyst, etc.) may also be used, for example, by heating at 60°C to 200°C (preferably 60°C to 100°C from the viewpoint of suppressing high molecular weight) for 1 hour to 10 hours.

[0101] The components constituting the above-mentioned branched polyester (A) are described in detail below.

[0102] Polyols with three or more reactive functional groups (a1)

[0103] As the above-mentioned polyols (a1) having three or more reactive functional groups, dicarboxylic acids and / or dicarboxylic anhydrides (a2), monoepoxides having long-chain hydrocarbon groups (a3), and chain extenders (a4), the aforementioned " Branched polyester (A) The compound described in the item "".

[0104] As a characteristic value of the above-mentioned branched polyester (A), from the viewpoint of satisfying various coating properties by reacting with a crosslinking agent in the case of coating, the hydroxyl value of the branched polyester (A) is preferably 1 mgKOH / g to 200 mgKOH / g, more preferably 10 mgKOH / g to 140 mgKOH / g, and even more preferably 20 mgKOH / g to 100 mgKOH / g.

[0105] Furthermore, the acid value of the branched polyester (A) is 50 mg KOH / g or less, preferably 15 mg KOH / g or less, more preferably 10 mg KOH / g or less, even more preferably 0.1 mg KOH / g or more and 10 mg KOH / g or less, and particularly preferably 0.1 mg KOH / g or more and 5 mg KOH / g or less.

[0106] The branched polyester (A) of the present invention is a low polarity resin that improves compatibility in solvent-based pigment dispersion compositions, and therefore the acid value that increases polarity is preferably low.

[0107] Furthermore, the number average molecular weight of the branched polyester (A) is preferably around 500 to 50,000, more preferably around 1,000 to 10,000, and even more preferably around 1,400 to 5,000.

[0108] Furthermore, from the viewpoint of compatibility and the synthesis reaction of the resin, the degree of branching of the branched polyester (A) is preferably 2.5 or more and 7 or less, more preferably 3.0 or more and 6.5 or less, and even more preferably 3.5 or more and 5.5 or less.

[0109] Here, the “degree of branching” of the present invention refers to the average theoretical value for a resin molecule under the condition that all resin raw materials have reacted. It is calculated by the number of branches in the resin skeleton based on the polyol (a1) and the chain extender (a4), without considering the branches at the resin ends (e.g., the case where the terminal hydrocarbon group of a monoepoxide compound has a branched structure).

[0110] Furthermore, depending on the number of reactive functional groups in the polyol (a1) and the chain extender (a4), the chain extender may sometimes connect the resin ends together. In such cases, the number of connected ends needs to be subtracted when calculating the "degree of branching".

[0111] Specifically, for example, the degree of branching of the resin is 3 when 1 mole of a trifunctional polyol, 3 moles of a dicarboxylic acid, and 3 moles of a monoepoxide compound are used as raw materials for the branched polyester. The degree of branching is 4 when 0.5 moles of diisocyanate are used as a chain extender in an additional reaction.

[0112] In addition, the degree of branching of resins with unbranched resin skeletons (two at the ends) is 2.

[0113] It should be noted that, in this specification, the number-average molecular weight and weight-average molecular weight are values ​​obtained by converting the retention time (retention capacity) determined using gel permeation chromatography (GPC) to the molecular weight of polystyrene based on the retention time (retention capacity) of a standard polystyrene with a known molecular weight determined under the same conditions. Specifically, the determination can be performed using four columns: “HLC8120GPC” (trade name, manufactured by Tosoh Corporation) for gel permeation chromatography, and “TSKgel G-4000HXL”, “TSKgel G-3000HXL”, “TSKgel G-2500HXL”, and “TSKgel G-2000HXL” (all trade names, manufactured by Tosoh Corporation) for the chromatographic columns, under the conditions of tetrahydrofuran as the mobile phase, a measurement temperature of 40°C, a flow rate of 1 mL / min, and a detector RI.

[0114] The amounts of polyols (a1) having three or more reactive functional groups, dicarboxylic acids and / or dicarboxylic anhydrides (a2), monoepoxides having long-chain hydrocarbon groups (a3), and chain extenders (a4) are as follows.

[0115] As for the amount of component (a2), based on the total amount of component (a1), component (a2) is preferably 100 mol% or more, more preferably 100 mol% to 500 mol%, and even more preferably 200 mol% to 400 mol%.

[0116] As for the amount of component (a3), based on the total amount of component (a2), component (a3) ​​is preferably 30 mol% to 300 mol%, more preferably 50 mol% to 200 mol%, and even more preferably 75 mol% to 150 mol%.

[0117] As the amount of component (a3) ​​based on the total amount of component (a1), component (a3) ​​is preferably 100 mol% or more, more preferably 100 mol% to 500 mol%, and even more preferably 200 mol% to 400 mol%.

[0118] Furthermore, the amount of component (a4) is preferably 0 mol% to 300 mol%, more preferably 20 mol% to 200 mol%, and even more preferably 40 mol% to 100 mol%, based on the total amount of component (a1).

[0119] While the exact reasons for the excellent compatibility (dispersibility, storage stability) of the branched polyester (A) obtained by the manufacturing method of the present invention with various resin components are not known, it is believed that the reason lies in the presence of alkyl components with lower polarity at the end of the branched resin, as well as the lower acid value (low polarity).

[0120] Furthermore, it is believed that lower molecular weight contributes to compatibility and higher concentration.

[0121] Furthermore, the branched polyester obtained using the manufacturing method of the present invention is particularly preferred as a branched polyester suitable for solvent-based pigment dispersion compositions, and can therefore be described as a branched polyester for solvent-based pigment dispersion compositions.

[0122] Pigment dispersion resin (B)

[0123] There are no particular limitations on the pigment dispersion resins used, and acrylic resins, polyester resins other than component (a1), alkyd resins, polyether resins, urethane resins, etc., are preferred. Resins with adsorption functional groups such as anionic, cationic, and nonionic properties are also preferred. In addition, commercially available products may also be used.

[0124] Pigment (C)

[0125] As the aforementioned pigment (C), known pigments can be used without limitation, such as coloring pigments, extender pigments, glossy pigments, etc.

[0126] Examples of such coloring pigments include: titanium dioxide, zinc oxide, carbon black, iron oxide red, molybdenum red, Prussian blue, cobalt blue, azo pigments, phthalocyanine pigments, quinacridone pigments, isoindoline pigments, vat pigments, perylene pigments, dioxazine pigments, and pyrrolopyrroledione pigments.

[0127] Examples of pigments that can be categorized as such include: clay, kaolin, barium sulfate, barium carbonate, calcium carbonate, talc, silicon dioxide, and alumina white.

[0128] Examples of bright pigments include: aluminum (including vapor-deposited aluminum), copper, zinc, brass, nickel, glass flakes, alumina, mica, alumina coated with titanium oxide and / or iron oxide, and mica coated with titanium oxide and / or iron oxide. Among aluminum pigments, both non-floating and floating types can be used.

[0129] Organic solvents (D)

[0130] Examples of organic solvents (D) mentioned above include: hydrocarbon solvents such as n-butane, n-hexane, n-heptane, n-octane, cyclopentane, cyclohexane, mineral oil, and cyclobutane; aromatic solvents such as solvent oil, toluene, and xylene; ketone solvents such as methyl isobutyl ketone; ether solvents such as n-butyl ether, dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, and diethylene glycol; and ethyl acetate, n-butyl acetate, isobutyl acetate, and ethylene glycol monomethyl ether acetate. Ester solvents such as butyl carbitol acetate; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and diisobutyl ketone; alcohol solvents such as ethanol, isopropanol, n-butanol, sec-butanol, and isobutanol; and amide solvents such as Equamide (trade name, manufactured by Idemitsu Kosan Co., Ltd.), N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N-methylacetamide, N-methylpropionamide, and N-methyl-2-pyrrolidone, etc., are all conventionally known solvents. They can be used alone or in combination of two or more.

[0131] Furthermore, if the amount is small, it can contain water within the range of dissolution, preferably less than 10% by mass of the total solvent, more preferably less than 5% by mass, and even more preferably less than 1% by mass.

[0132] Other ingredients

[0133] The solvent-based pigment dispersion composition of the present invention may contain various resins, additives, etc. as other components.

[0134] Examples of the aforementioned resins include, for example, polyester resins other than branched polyesters (A), acrylic resins, epoxy resins, polyether resins, alkyd resins, urethane resins, silicone resins, polycarbonate resins, silicate resins, chlorinated resins, fluorinated resins, and composite resins thereof.

[0135] As the aforementioned additives, they may include, for example, well-known paint additives such as ultraviolet absorbers (e.g., benzotriazole absorbers, triazine absorbers, salicylic acid derivative absorbers, benzophenone absorbers, etc.), light stabilizers (e.g., hindered amines, etc.), tackifiers, defoamers, surface conditioners, anti-settling agents, rust inhibitors, chelating agents (acetylacetone, etc.), dehydrating agents, neutralizing agents, and plasticizers.

[0136] It should be noted that the solvent-based pigment dispersion composition of the present invention is a pigment dispersion composition for color matching, and therefore preferably does not contain a curing agent. The curing agent is preferably mixed in during the coating manufacturing process.

[0137] The solvent-based pigment dispersion composition of the present invention described above can be a composition containing a coloring pigment.

[0138] The solvent-based pigment dispersion composition of the present invention is a composition containing the above-mentioned branched polyester (A), pigment dispersion resin (B), pigment (C), and organic solvent (D). As a manufacturing method, the components containing pigment dispersion resin (B), pigment (C), and organic solvent (D) are mixed, and the pigment is dispersed to form a liquid paste. Furthermore, regarding the branched polyester (A), it can be formulated before and / or after pigment dispersion; preferably, it is mixed with components (B), (C), and (D) before pigment dispersion, and pigment dispersion is performed together with them.

[0139] As a method for pigment dispersion, known methods can be used without limitation, such as bead mills, ultrasonic homogenizers, high-pressure homogenizers, paint shakers, ball mills, roller mills, sand mills, sand grinders, DYNO-MILL mills, nanomizers, and other dispersants. Dispersion methods using media are particularly preferred.

[0140] The solid component of the solvent-based pigment dispersion composition of the present invention is preferably 20% to 85% by mass, more preferably 30% to 70% by mass, and even more preferably 35% to 75% by mass.

[0141] Furthermore, the solvent-based pigment dispersion composition of the present invention requires a high concentration of pigment. Based on the total mass of the solvent-based pigment dispersion composition, it preferably contains 5% to 70% by mass of pigment (C), more preferably 15% to 65% by mass of pigment (C), and even more preferably 20% to 60% by mass of pigment (C).

[0142] Furthermore, based on the solid composition of the solvent-based pigment dispersion composition, it is preferable to contain 5% to 70% by mass of branched polyester (A), more preferably 7% to 60% by mass of branched polyester (A), and even more preferably 10% to 55% by mass of branched polyester (A).

[0143] Furthermore, based on the solid content of the solvent-based pigment dispersion composition, it is preferable to contain 1% to 50% by mass of pigment dispersion resin (B), more preferably 2% to 35% by mass of pigment dispersion resin (B), and even more preferably 3% to 20% by mass of pigment dispersion resin (B).

[0144] According to the present invention, by using a solvent-based pigment dispersion composition containing a certain amount of branched polyester (A) having a specific structure, the following problems can be solved: providing a solvent-based pigment dispersion composition containing a resin that is well compatible with various pigment dispersion pastes and various resins, and further providing a high-concentration solvent-based pigment dispersion composition.

[0145] Solvent-based coating compositions

[0146] As a second aspect of the present invention, multiple (multi-colored) solvent-based pigment dispersion compositions described above can be prepared, mixed in a manner that achieves the desired color, and further mixed with a base coating, resin, and / or additives corresponding to the desired color to manufacture a solvent-based coating composition. It should be noted that the aforementioned base coating refers to a coating composition containing various resins and / or additives without coloring pigments, or a coating containing various white resins and / or additives, which may contain extender pigments as needed.

[0147] As a method for manufacturing the above-mentioned solvent-based coating composition, the solvent-based pigment dispersion composition (various types) of the present invention and the required base coating, resin and / or additives can be added to a mixing tank, and the mixture can be thoroughly stirred and mixed using a rotary stirring blade to obtain a tinted coating composition.

[0148] Furthermore, since the solvent-based pigment dispersion composition of the present invention has good compatibility, it is also preferable to use a mixing method (color mixing method) that does not utilize a rotary stirring blade.

[0149] For example, in the above mixing process, a solvent-based paint composition can be obtained by a mixing method (color mixing method) that involves "adding the solvent-based pigment dispersion composition (various types) of the present invention and the required base paint, resin and / or additives to the same paint can, covering the paint can lid and shaking the can to mix them evenly".

[0150] The above mixing method allows for the production of paint cans without the use of a mixing tank, thus enabling efficient and inexpensive paint manufacturing. Furthermore, it reduces the generation of cleaning solvents caused by cleaning the mixing tank.

[0151] As for the above-mentioned solvent-based coating composition, it is preferable to finally mix it with a curing agent and apply it to the substrate to form a coating film crosslinked by the curing agent. As a curing agent, melamine resin, polyisocyanate compound and / or block polyisocyanate compound are preferred.

[0152] The solvent-based coating compositions described above can be used without limitation as coatings for automobiles, electrical products, steel furniture, office supplies, building materials, buildings, bridges, etc., except for ink and inkjet applications.

[0153] Example

[0154] The present invention will be further described in detail below using manufacturing examples, embodiments, and comparative examples, but the present invention is not limited thereto. In the examples, "parts" refers to parts by mass, and "%" refers to percentages by mass.

[0155] Manufacturing of branched polyester (A)

[0156] Example (1-1)

[0157] 136.5 parts of trimethylolpropane, 444 parts of phthalic anhydride, and 735 parts of neodecanoic acid monoglycidyl ester were charged into a reactor equipped with a stirrer, reflux cooler, water separator, and thermometer, and reacted at 180°C for 3 hours. (No condensation water was produced.)

[0158] Next, 84 parts of hexamethylene diisocyanate were reacted at 100°C for 2 hours. Then, while cooling, "Swazol 1000" (trade name, manufactured by Cosmo Oil, an aromatic organic solvent) was added. The result was a 50% solids solution of branched polyester (A-1) with an acid value of 3 mg KOH / g, a hydroxyl value of 83 mg KOH / g, a number-average molecular weight of 2400, and a degree of branching of 4.0.

[0159] Examples (1-16)

[0160] 137 parts of trimethylolpropane and 444 parts of phthalic anhydride were charged into a reactor equipped with a stirrer, reflux cooler, water separator, and thermometer, and reacted at 180°C for 3 hours. (A small amount of condensation water was produced.)

[0161] Next, 735 parts of neodecanoic acid monoglycidyl ester were added and reacted at 180°C for 3 hours. Then, 84 parts of hexamethylene diisocyanate were reacted at 100°C for 2 hours. Afterward, "Swazol 1000" (trade name, manufactured by Cosmo Oil, an aromatic organic solvent) was added while cooling. The result was a 50% solids solution of branched polyester (A-16) with an acid value of 3 mg KOH / g, a hydroxyl value of 83 mg KOH / g, a number-average molecular weight of 2400, and a degree of branching of 4.0.

[0162] Examples (1-2) to (1-15), Comparative Examples (1-1) and (1-2)

[0163] Polyesters (A-2) to (A-15), (A-17), and (A-18) were manufactured in the same manner as in Example 1, except that the types and amounts specified in Table 1 below are used. The characteristic values ​​of the resins are shown in the table.

[0164] Table 1

[0165]

[0166]

[0167] TMP: Trimethylolpropane

[0168] G: Glycerin

[0169] PE: Pentaerythritol

[0170] DMPA: Dimethylolpropionic acid

[0171] 1,6HD: 1,6-Hexanediol

[0172] HHPA: Hexahydrophthalic anhydride

[0173] PA: Phthalic anhydride

[0174] BA: Benzoic acid

[0175] NDGE: Neodecanoic acid monoglycidyl ester

[0176] BGE: n-Butyl glycidyl ether

[0177] HMDI: Hexamethylene diisocyanate

[0178] IPDI: Isophorone diisocyanate

[0179] The abbreviations in Table 1 above are as described above.

[0180] Example 1: Manufacturing of Pigment Dispersion Resin

[0181] 300 parts of "Swazol 1500" (trade name, manufactured by Cosmo Oil, an aromatic organic solvent) were added to a manufacturing flask equipped with a thermometer, thermostat, stirring device, reflux cooler and dropping device. The temperature was raised to 115°C, and the monomer composition described below was added dropwise over 3 hours while stirring and mixing in a nitrogen stream.

[0182] <Monomer Composition>

[0183]

[0184]

[0185] <Catalyst Mixture>

[0186] 300 servings of “Swazol 1500”

[0187] 5 parts of 2,2'-azobis(2,4-dimethylpentanonitrile)

[0188] Next, the above catalyst mixture was added dropwise over 1 hour at this temperature, and after maturing at 115°C for 1 hour, "Swazol 1500" (trade name, manufactured by Cosmo Oil, an aromatic organic solvent) was added to obtain a pigment dispersion resin solution with 50% solids content.

[0189] Preparation of solvent-based pigment dispersion compositions

[0190] Example 1A

[0191] 20g of polyester resin (A-1) solution obtained in Example 1-1 (10g solid content), 10g of pigment dispersion resin solution obtained in Manufacturing Example 1 (5g solid content), 25g of carbon black, and 30g of "Swazol 1000" (trade name, manufactured by Cosmo Oil, an aromatic organic solvent) were added to a 225ml wide-mouth glass bottle. 100g of glass beads with a diameter of about 1.5mm were added as a dispersion medium and the bottle was sealed. The mixture was dispersed for 60 minutes using a DASH2000-K DISPERSER (trade name, manufactured by LAU, a vibrating paint conditioner) to obtain a solvent-based pigment dispersion composition (X-1A).

[0192] Example 1B

[0193] By replacing 25g of carbon black with 35g of iron oxide red in the solvent-based pigment dispersion composition (X-1A) of Example 1A above, the same procedure was carried out to obtain a solvent-based pigment dispersion composition (X-1B) with a different color.

[0194] Examples 2A to 17A and Comparative Examples 1A to 3A

[0195] The formulations (types and amounts of resin) were set as shown in Table 2 below. Otherwise, the same procedure was followed as for the solvent-based pigment dispersion composition (X-1A) of Example 1A, and solvent-based pigment dispersion compositions (X-2A) to (X-20A) were obtained.

[0196] Examples 2B-17B and Comparative Examples 1B-3B

[0197] The formulations (types and amounts of resin) were set as shown in Table 2 below. Otherwise, the same procedure was followed as for the solvent-based pigment dispersion composition (X-1B) of Example 1B, resulting in solvent-based pigment dispersion compositions (X-2B) to (X-20B).

[0198] That is, pigment dispersion compositions (X-1A) to (X-20A) containing carbon black (A series) and pigment dispersion compositions (X-1B) to (X-20B) containing iron oxide red (B series) are respectively manufactured.

[0199] Table 2

[0200]

[0201] (Continued)

[0202]

[0203] (Continued)

[0204]

[0205] It should be noted that the amounts in Table 2 above are values ​​for solid components.

[0206] Furthermore, the results of the evaluation tests described later are shown in Table 2 above. (Example 1C is an evaluation result of a coating containing components of solvent-based pigment dispersion compositions of Examples 1A and 1B, respectively. Other examples and comparative examples were also evaluated in the same way.)

[0207] In the solvent-based pigment dispersion composition (solvent-based coating composition) of the present invention, all evaluation tests are required to pass. An "×" in any evaluation test indicates failure; all other results indicate success.

[0208] <Evaluation Experiment>

[0209] Coating appearance

[0210] A paint composition (dispersed product) was prepared by mixing 100 parts of solids of "Cera M Retan White" (trade name, acrylic / urethane-based weak solvent paint) manufactured by Kansai Paint Co., Ltd., with 10 parts of solids of a black pigment dispersion composition containing carbon black (Series A) and 10 parts of solids of a red pigment dispersion composition containing iron oxide red (Series B) obtained in the Examples and Comparative Examples, and stirring in a disperser for 30 minutes.

[0211] Next, a coating was applied using a coating machine to achieve a dry film thickness of 50 μm. After drying at room temperature for 3 days, the appearance of the coating was visually evaluated according to the following criteria.

[0212] ○: The gloss and vividness are both excellent.

[0213] Δ: Slightly worse in either gloss or vividness.

[0214] ×: The gloss and vividness are significantly worse.

[0215] In-can color adjustment

[0216] In addition to 100 parts of the solids component of "Cera M Retan White" (trade name, acrylic / urethane-based solvent-based paint) manufactured by Kansai Paint, a black pigment dispersion composition containing carbon black (Series A) obtained in the Examples and Comparative Examples was mixed into the paint can at a solids component of 10 parts. Furthermore, a red pigment dispersion composition containing iron oxide red (Series B) was mixed into the paint can at a solids component of 10 parts. The can was then capped and shaken for 20 minutes to mix, thus producing the paint composition (tinting agent in the can).

[0217] In addition, a coating composition (dispersed product) was prepared separately using the same formulation and subjected to dispersion stirring for 30 minutes.

[0218] As described above, each coating composition prepared by the two methods was applied to tinplate using a coating machine within one hour after manufacturing, with the dried film thickness reaching 50 μm, and the results were visually evaluated according to the following criteria.

[0219] ○: No color difference was found between the colorant in the tank and the product stirred in the disperser.

[0220] Δ: A slight color difference was detected between the colorant in the tank and the product stirred in the disperser.

[0221] ×: A significant color difference was found between the colorant in the tank and the product stirred in the disperser.

[0222] Color grading stability (storage stability)

[0223] The coating composition (dispersant-stirred sample) prepared in the above-described coating appearance evaluation test was spray-coated (50 μm dry film) onto a tinplate within 1 hour of manufacture. After drying at room temperature for 3 days, the same coating composition was applied using a brush and roller. Visual evaluation was performed according to the following criteria. In this evaluation, in addition to storage stability, color uniformity due to coating type (different shear rates, etc.) was also observed.

[0224] ○: No color difference was found between the coated surfaces obtained by spraying, brushing, and rolling respectively.

[0225] Δ: It was confirmed that there was a slight color difference between the coated surfaces obtained by spraying, brushing, and rolling respectively.

[0226] ×: It was confirmed that there was a significant color difference between the coated surfaces obtained by spraying, brushing, and rolling respectively.

Claims

1. A solvent-based pigment dispersion composition, characterized in that, It is a solvent-based pigment dispersion composition containing branched polyester (A), pigment dispersion resin (B), pigment (C), and organic solvent (D). Branched polyester (A) contains components comprising the following substances as constituents: a polyol (a1) having three or more reactive functional groups, a dicarboxylic anhydride (a2), and a monoepoxide compound (a3) ​​having six or more hydrocarbon groups. Polyols (a1) with reactive functional groups of 3 or more functions are trimethylolpropane and / or glycerol. Based on the total amount of polyols (a1) with 3 or more reactive functional groups, the amount of monoepoxide compounds (a3) ​​with 6 or more carbon atoms is 200 mol% to 400 mol%. The branched polyester (A) has an acid value below 10 mg KOH / g and a hydroxyl value between 20 mg KOH / g and 100 mg KOH / g. This solvent-based pigment dispersion composition contains 10% to 55% by mass of branched polyester (A) based on its solids content.

2. The solvent-based pigment dispersion composition according to claim 1, wherein, The branched polyester (A) further contains a chain extender (a4) as a constituent component.

3. The solvent-based pigment dispersion composition according to claim 1, wherein, The number average molecular weight of branched polyester (A) is 500 to 50,000, and the degree of branching is 2.5 to 7.

4. The solvent-based pigment dispersion composition according to claim 1, wherein, Based on the total mass of the solvent-based pigment dispersion composition, it contains 5% to 70% by mass of pigment (C).

5. The solvent-based pigment dispersion composition according to claim 1, wherein, The method for manufacturing the branched polyester (A) includes the following steps performed sequentially: Step 1-1: A step of reacting the polyol (a1) containing the reactive functional groups having three or more functions and the dicarboxylic anhydride (a2) to form an intermediate product. Step 1-2: A step of reacting the components comprising the intermediate product and the monoepoxide compound (a3) ​​having a hydrocarbon group having 6 or more carbon atoms.

6. The solvent-based pigment dispersion composition according to claim 5, wherein, In the method for manufacturing the branched polyester (A), after steps 1-1 and 1-2, the following is included: Steps 1-3: Steps that further react the components containing the chain extender (a4).

7. The solvent-based pigment dispersion composition according to claim 1, wherein, The method for manufacturing the branched polyester (A) includes the following steps: Step 2-1: A step in which the components comprising the polyol (a1) having three or more reactive functional groups, the dicarboxylic anhydride (a2), and the monoepoxide compound (a3) ​​having six or more carbon atoms react simultaneously.

8. The solvent-based pigment dispersion composition according to claim 7, wherein, In the method for manufacturing the branched polyester (A), after step 2-1, the following is included: Step 2-2: A further step in reacting the components containing the chain extender (a4).

9. A method for manufacturing the solvent-based pigment dispersion composition according to any one of claims 5 to 8, characterized in that, The branched polyester (A), the pigment dispersion resin (B), the pigment (C), and the organic solvent (D) are mixed, and then the pigment is dispersed using a medium to obtain the solvent-based pigment dispersion composition.

10. The method for manufacturing the solvent-based pigment dispersion composition according to claim 9, wherein, Based on the total mass of the solvent-based pigment dispersion composition, it contains 5% to 70% by mass of pigment (C).

11. A solvent-based coating composition, characterized in that, It is obtained by mixing multiple, i.e., multi-colored, solvent-based pigment dispersion compositions as described in any one of claims 1 to 4.

12. A method for manufacturing a solvent-based coating composition, characterized in that, Prepare multiple, i.e., multi-colored, solvent-based pigment dispersion compositions as described in any one of claims 1 to 4, and add multiple such solvent-based pigment dispersion compositions to the same paint can for color matching.

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