Viscosity modifier for non-aqueous coating material and non-aqueous coating material composition

Abstract

Provided are: a viscosity modifier for a non-aqueous coating material having an excellent viscosity-imparting effect even when an amide-based viscosity modifier formed from a fatty acid diamide is added to an ultra-high solid coating material or a solvent-free coating material; and a non-aqueous coating material composition containing the viscosity modifier and thus having excellent sagging prevention properties.　The present invention is a viscosity modifier for a non-aqueous coating material, the viscosity modifier comprising a fatty acid diamide obtained through a condensation reaction of a diamine component and a monocarboxylic acid component, wherein the diamine component is 1,4-diaminobutane, and the non-aqueous coating material is a solvent-free coating material or an ultra-high solid coating material.

Description

Viscosity modifier for non-aqueous paint and non-aqueous paint composition

[0001] The present invention relates to a viscosity modifier for non-aqueous paints and a non-aqueous paint composition containing the viscosity modifier.

[0002] Viscosity modifiers (also called "thixotropic agents") for marine or heavy-duty anticorrosion paints containing organic solvents include fine powders of clay minerals such as bentonite, hydrogenated castor oil, and fatty acid diamides. Among these, viscosity modifiers using fine powders of fatty acid diamides (hereinafter referred to as "amide-based viscosity modifiers") are widely used due to their excellent anti-sagging properties, water resistance, and thermal stability.

[0003] For example, Patent Document 1 discloses a flow property modifier for organic vehicles, which comprises a fatty acid diamide obtained by reacting a mixture of hydrogenated castor oil fatty acid and a linear saturated fatty acid having 6 to 12 carbon atoms with an equivalent ratio of the fatty acid to ethylenediamine (hereinafter sometimes referred to as "EDA") or 1,4-diaminobutane (hereinafter sometimes referred to as "1,4-DAB"). The mixing ratio of the hydrogenated castor oil fatty acid to the linear saturated fatty acid in the mixture is within a molar ratio of 8:2 to 3:7.

[0004] Japanese Unexamined Patent Publication No. 56-112977

[0005] In recent years, in the fields of marine and heavy-duty anticorrosion paints, there has been active research into ultra-high solid paints that use as little solvent as possible and solvent-free paints that do not use any organic solvents, in order to reduce the environmental impact.

[0006] In order for the amide-based viscosity modifier to exert its viscosity-imparting and sagging-preventing effects, it is necessary to heat and swell the fatty acid diamide in the paint to which the viscosity modifier has been added. By heating and swelling the fatty acid diamide in this way, the fatty acid diamide is activated (changed to a needle-like shape), and can stably impart viscosity to the paint system.

[0007] However, when the amide-based viscosity modifiers that have traditionally been used in ultra-high solids paints and solvent-free paints are added, it is difficult to fully activate the fatty acid diamides in the paint, and they are unable to exert a sufficient viscosity-imparting effect, which can result in problems with sagging when painted on vertical surfaces, etc.

[0008] Thus, there has been a demand for amide-based viscosity modifiers that have excellent viscosity-imparting effects and anti-sagging properties in ultra-high solid paints in which the amount of solvent is reduced as much as possible and solvent-free paints that do not use organic solvents.

[0009] Therefore, the present invention has been made in consideration of the above circumstances, and aims to provide a viscosity modifier for non-aqueous paints that has an excellent viscosity-imparting effect even when an amide-based viscosity modifier made of a fatty acid diamide is added to an ultra-high solids paint or a solvent-free paint, and a non-aqueous paint composition that contains this viscosity modifier and thereby has excellent sagging prevention properties.

[0010] As a result of extensive research into solving the above problems, the present inventors have found that by using 1,4-DAB as a diamine component, which is a raw material for synthesizing a fatty acid diamide used as a viscosity modifier, an excellent viscosity-imparting effect can be achieved even when an amide-based viscosity modifier is added to an ultra-high solids paint or a solvent-free paint, and have completed the present invention based on this finding.

[0011] That is, the present invention relates to a viscosity modifier for non-aqueous paints, which comprises a fatty acid diamide obtained by subjecting a diamine component and a monocarboxylic acid component to a condensation reaction, wherein the diamine component is 1,4-diaminobutane, and the non-aqueous paint is a solventless paint or an ultra-high solids paint.

[0012] In one aspect of the present invention, the monocarboxylic acid component is preferably a mixture of hydrogenated castor oil fatty acid and linear saturated fatty acid, and in this case, the linear saturated fatty acid more preferably has 8 to 10 carbon atoms.

[0013] In another aspect of the present invention, the monocarboxylic acid component preferably contains a linear saturated fatty acid having from 8 to 10 carbon atoms.

[0014] Another aspect of the present invention is a non-aqueous coating composition containing a viscosity modifier and a resin, characterized in that the viscosity modifier comprises a fatty acid diamide obtained by a condensation reaction of a diamine component and a monocarboxylic acid component, the diamine component is 1,4-diaminobutane, and the non-aqueous coating composition is a solventless coating or an ultra-high solids coating.

[0015] In one aspect of the present invention, the monocarboxylic acid component is preferably a mixture of hydrogenated castor oil fatty acid and linear saturated fatty acid. In this case, it is more preferable that the linear saturated fatty acid has 8 to 10 carbon atoms.

[0016] In another aspect of the present invention, the monocarboxylic acid component preferably contains a linear saturated fatty acid having from 8 to 10 carbon atoms.

[0017] According to the present invention, by using 1,4-DAB as a diamine component that is a raw material for synthesizing a fatty acid diamide used as a viscosity modifier for a non-aqueous paint, it becomes possible to achieve an excellent viscosity-imparting effect even when an amide-based viscosity modifier is added to an ultra-high solids paint or a solvent-free paint.

[0018] Preferred embodiments of the present invention will now be described in detail.

[0019] [Viscosity modifier for non-aqueous paint] The viscosity modifier according to the present invention is an additive used in non-aqueous paint, and is composed of a specific fatty acid diamide.

[0020] (Fatty Acid Diamide) The fatty acid diamide according to the present invention is a fatty acid diamide obtained by a condensation reaction of a diamine component and a monocarboxylic acid component, and the diamine component is 1,4-diaminobutane (1,4-DAB). That is, the diamine component used in the synthesis of the fatty acid diamide according to the present invention is only 1,4-DAB.

[0021] The fatty acid diamide of the present invention may be, for example, a fatty acid diamide (a) having three main components: N-12 hydroxystearic acid N'-alkanoic acid tetramethylenediamide, N,N'-12 hydroxystearic acid tetramethylenediamide, and N,N'-alkanoic acid tetramethylenediamide. This fatty acid diamide (a) can be obtained by adding an equivalent amount of 1,4-DAB to a mixture of hydrogenated castor oil fatty acid and linear saturated fatty acid (hereinafter simply referred to as "alkanoic acid") and carrying out an amidation reaction. Therefore, when fatty acid diamide (a) is used as the fatty acid diamide of the present invention, the diamine component is 1,4-DAB, and the monocarboxylic acid component is a mixture of hydrogenated castor oil fatty acid and alkanoic acid.

[0022] The general formula of the main component contained in the fatty acid diamide (a) is as follows: (1) N-12 hydroxystearic acid N'-alkanoic acid tetramethylenediamide CH ３ (CH ２ ) ５ CHOH (CH ２ ) １０ CONH (CH ２ ) ４ NHCO(CH ２ ) ｌ CH ３ (In the above general formula, l is a natural number.) (2) N,N'-12-hydroxystearic acid tetramethylenediamide CH ３ (CH ２ ) ５ CHOH (CH ２ ) １０ CONH (CH ２ ) ４ NHCO(CH ２ ) １０ CHOH (CH ２ ) ５ CH ３ (3) N,N'-alkanoic acid tetramethylenediamide CH ３ (CH ２ ) ｎ CONH (CH ２ ) ４ NHCO(CH ２ ) ｍ CH３ (In the above general formula, n and m are each a natural number.)

[0023] In addition to the above three components (1) to (3), the fatty acid diamide (a) also contains small amounts of unreacted raw materials and by-products.

[0024] The fatty acid diamide according to the present invention is not limited to the fatty acid diamide (a) described above, but may be any other fatty acid diamide obtained by the condensation reaction of a diamine component and a monocarboxylic acid component, as exemplified below. The conditions for the condensation reaction (such as reaction temperature and the blending ratio of each component) may be appropriately determined by a known method.

[0025] <Diamine Component> As described above, only 1,4-DAB is used as the diamine component in the present invention.

[0026] <Monocarboxylic Acid Component> The monocarboxylic acid component of the present invention is not particularly limited, and may include, for example, a straight-chain saturated fatty acid (alkanoic acid). Examples of alkanoic acids that can be used as the monocarboxylic acid component of the present invention include saturated aliphatic monocarboxylic acids such as acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid (behenic acid). Among these, saturated aliphatic monocarboxylic acids having 12 or less carbon atoms (such as acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, and lauric acid) can be used as the alkanoic acid. When a fatty acid diamide containing such an alkanoic acid is used, the viscosity modifier of the present invention can effectively exert its viscosity-imparting effect.

[0027] Among these alkanoic acids, the viscosity-imparting effect of the viscosity modifier of the present invention is further enhanced when an alkanoic acid having from 8 to 10 carbon atoms is used, and as a result, the nonaqueous coating composition of the present invention containing a viscosity modifier comprising a fatty acid diamide obtained using an alkanoic acid having from 8 to 10 carbon atoms has very excellent sagging prevention properties.

[0028] The monocarboxylic acid component according to the present invention may also contain hydrogenated castor oil fatty acid. When the fatty acid diamide uses hydrogenated castor oil fatty acid, the viscosity modifier of the present invention can effectively exert a viscosity-imparting effect.

[0029] Furthermore, hydrogenated castor oil fatty acid and alkanoic acid can be used in combination as the monocarboxylic acid component to be condensed with the diamine component to synthesize the fatty acid diamide of the present invention. Using a mixture of hydrogenated castor oil fatty acid and alkanoic acid as the monocarboxylic acid component further enhances the viscosity-imparting effect of the viscosity modifier of the present invention. As a result, the non-aqueous coating composition of the present invention containing the viscosity modifier composed of the fatty acid diamide obtained using such a monocarboxylic acid component has excellent sagging prevention properties.

[0030] Other examples of the monocarboxylic acid component that can be used in the present invention include unsaturated aliphatic monocarboxylic acids such as oleic acid, linoleic acid, ricinoleic acid, linolenic acid, eicosenoic acid, erucic acid, and mixed fatty acids obtained from natural fats and oils (tall oil fatty acid, rice bran fatty acid, soybean oil fatty acid, beef tallow fatty acid, etc.).

[0031] <Method for Synthesizing Fatty Acid Diamide> The fatty acid diamide of the present invention can be obtained by adding an equivalent amount of the diamine component to the monocarboxylic acid component and carrying out a condensation polymerization (amidation) reaction at 150 to 200°C. For example, the raw materials, the diamine component (containing at least 1,4-DAB) and the monocarboxylic acid component, are placed in a reaction vessel such as a four-necked flask, and the raw materials are stirred in an inert gas atmosphere (e.g., under a nitrogen gas flow) to form a mixture. The raw material mixture is then heated and subjected to a condensation polymerization reaction at 150 to 200°C for 4 to 10 hours, thereby synthesizing the fatty acid diamide of the present invention.

[0032] (Hydrogenated Castor Oil) The viscosity modifier of the present invention may contain hydrogenated castor oil to the extent that the effects of the present invention are not impaired. Hydrogenated castor oil is a triglyceride of saturated fatty acids obtained by hydrogenating castor oil. Commercially available hydrogenated castor oils can be used, and examples of commercially available hydrogenated castor oils include C-Wax (manufactured by Kokura Synthetic Industries Co., Ltd.), Kaowax 85P (manufactured by Kao Corporation), Castor Hydrogenated Oil A (manufactured by Ito Oil Mills Co., Ltd.), and Castor Hydrogenated Oil (manufactured by Yamakei Sangyo Co., Ltd.).

[0033] (Method for Producing Viscosity Modifier) ​​The viscosity modifier of the present invention described above can be produced as follows. For example, the fatty acid diamide synthesized as described above is extracted as a solid from a melt. This solid fatty acid diamide is pulverized to a desired particle size to produce a powdered viscosity modifier made of fatty acid diamide. There are no particular restrictions on the method for pulverizing the solid fatty acid diamide, but a jet mill or the like can be used, for example. There are also no particular restrictions on the particle size during pulverization, but it may be, for example, about 1 to 50 μm.

[0034] (Uses of Viscosity Modifier) ​​The viscosity modifier of the present invention is suitable for use as an additive for non-aqueous paints. Examples of non-aqueous paints include marine paints and heavy-duty anticorrosion paints. When using the viscosity modifier of the present invention as an additive for non-aqueous paints, as described above, it is preferable to pulverize the solid fatty acid diamide to form a powdered viscosity modifier. Here, the non-aqueous paints using the viscosity modifier of the present invention are limited to solventless paints or ultra-high solid paints. Details of "solventless paints" and "ultra-high solid paints" will be described later.

[0035] [Non-aqueous Paint Composition] The non-aqueous paint composition of the present invention contains the above-mentioned viscosity modifier and a resin as essential components. The amide-based viscosity modifier is activated by heat dispersion in the non-aqueous paint, exhibiting its viscosity modifier effects (e.g., viscosity-imparting effect). However, the degree of activation is affected by the paint formulation and heat dispersion conditions (e.g., temperature, dispersion shear, dispersion time). On the other hand, when the paint formulation and heat dispersion conditions are the same, the ease of activation is determined by the viscosity modifier composition, so the effects of the present invention are not limited by the content of viscosity modifier in the paint. However, if the content of viscosity modifier in the paint is too low, the viscosity modifier effect is weak. On the other hand, if the content of viscosity modifier in the paint is too high, the paint will thicken significantly, making dispersion of the viscosity modifier in the paint, handling of the paint, and application difficult. Therefore, the content of viscosity modifier in the non-aqueous paint composition is preferably 0.2% to 5% by mass.

[0036] The non-aqueous coating composition of the present invention is a solventless coating or an ultra-high solids coating. Solventless coatings are coatings that do not contain volatile solvents (such as organic solvents) to dissolve the resin in the coating, and have the advantage of contributing to low VOCs because there is no need to volatilize the solvent during coating film formation. Furthermore, because they do not contain volatile solvent components, the applied thickness is almost the same as the thickness after drying, making them suitable for coating applications where a large coating thickness is desired. Furthermore, ultra-high solids coatings are coatings in which the content of volatile solvents in the coating is reduced as much as possible. In this invention, coatings in which the content of volatile solvents in the coating is 15% by mass or less based on the total amount of the coating are referred to as "ultra-high solids coatings."

[0037] Generally, as mentioned above, "solvent-free paint" refers to paint that does not contain volatile solvents in the paint, but may contain liquid components (components that remain in the paint film) such as reactive diluents, non-reactive diluents, silane coupling agents, etc., as necessary. Therefore, in the present invention, "solvent-free paint" includes not only completely solvent-free paints that are completely free of liquid components that can function as solvents, but also paints that contain the above-mentioned components that remain in the paint film and do not contain volatile solvents. Examples of the reactive diluent include acrylates such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, and phenyl glycidyl ether acrylate; urethane prepolymers such as hexamethylene diisocyanate urethane prepolymer and phenyl glycidyl ether acrylate toluene diisocyanate urethane prepolymer; glycidyl ethers such as n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, glycidyl ether of stearic acid, styrene oxide, phenyl glycidyl ether, nonylphenyl glycidyl ether, butylphenyl glycidyl ether, 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, and diethylene glycol diglycidyl ether; chlorostyrene, methoxystyrene, butoxystyrene, and vinylbenzoic acid. Suitable examples of non-reactive diluents include petroleum resin diluents, such as aliphatic or aromatic high-boiling oils, phenol-modified aliphatic or aromatic polymers, xylene resins, and toluene resins.

[0038] (Solvent) The solvent in the present invention, that is, the volatile solvent for dissolving the resin in the coating material, may be, for example, an organic solvent, and is not particularly limited as long as it is used in the coating material field.

[0039] Examples of organic solvents include alcohols such as methanol, ethanol, isopropyl alcohol, 1-butanol (n-butanol), 2-butanol, 1-pentanol, octyl alcohol, benzyl alcohol, glycerin, ethylene glycol, and propylene glycol; carboxylic acids such as acetic acid; aliphatic hydrocarbons such as hexane, heptane, octane, and decane; aromatic hydrocarbons such as toluene and xylene; amides such as dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, and acetanilide; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; halogens such as methylene chloride and chloroform; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, and diethyl carbonate; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl butyrate, and propylene glycol monomethyl ether acetate (PMA); ethers such as propylene glycol monomethyl ether (PM); acetonitrile, propionitrile, and the like. The above-mentioned solvents may be used alone or in combination of two or more kinds.

[0040] (Organic Medium) In the non-aqueous coating composition containing the solvent of the present invention (solvent-containing coating), an organic medium containing a reactive functional group or a non-reactive organic medium may be used in combination with the above-mentioned solvent.

[0041] Examples of organic media containing a reactive functional group include acrylates such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, and phenyl glycidyl ether acrylate; urethane prepolymers such as hexamethylene diisocyanate urethane prepolymer and phenyl glycidyl ether acrylate toluene diisocyanate urethane prepolymer; glycidyl ethers such as n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, glycidyl ether of stearic acid, styrene oxide, phenyl glycidyl ether, nonylphenyl glycidyl ether, butylphenyl glycidyl ether, 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, and diethylene glycol diglycidyl ether; chlorostyrene, methoxystyrene, butoxystyrene, and vinylbenzoic acid.

[0042] Suitable examples of non-reactive organic media include petroleum resin-based organic media having a viscosity of 1 to 200 cps at 25° C. and a heating residue of 90% or more. Examples of petroleum resin-based organic media include aliphatic or aromatic high-boiling oils, phenol-modified aliphatic or aromatic polymers, xylene resins, and toluene resins.

[0043] (Resin) The non-aqueous coating composition of the present invention further contains a resin as a main component for forming a coating film.

[0044] The resins for paints that can be used with the non-aqueous paint composition of the present invention are not particularly limited as long as they are resins that have traditionally been used as base resins for non-aqueous paints, and various resins can be incorporated into the non-aqueous paint composition. Examples of base resins for non-aqueous paints that can be used with the non-aqueous paint composition of the present invention include alkyd resins, acrylic resins, acrylic urethane resins, melamine resins, urethane resins, epoxy resins, coumarone resins, urea resins, phenolic resins, vinyl chloride resins, phenoxy resins, silicone resins, fluororesins, nylon resins, styrene-butadiene resins, nitrile-butadiene resins, petroleum resins, rosin, drying oil, boiled oil, acetyl cellulose, nitrocellulose, etc. These resins may be cured by a chemical reaction with or without a catalyst, such as heat-curable, ultraviolet-curable, electron-beam-curable, oxidation-curable, photocation-curable, peroxide-curable, or acid / epoxy-curable resins. They may also be resins with a high glass transition point that form a coating simply by volatilizing the diluent without a chemical reaction. Examples of the curing agent include amino resins, melamine resins, isocyanate compounds, blocked isocyanate compounds, and epoxy compounds. Only one type of base resin may be used, or two or more types may be used in combination.

[0045] From the viewpoint of film-forming properties, the content of the resin in the non-aqueous coating composition is preferably 20 to 99.5% by mass.

[0046] (Filler) The non-aqueous coating composition of the present invention may further contain a filler such as an extender pigment, a color pigment, or a metallic pigment, from the viewpoint of improving the appearance and properties of the coating film.

[0047] Examples of fillers include extender pigments such as calcium carbonate (heavy calcium carbonate (GCC), precipitated calcium carbonate (PCC), etc.), barium sulfate, silicon dioxide, aluminum hydroxide, talc, organic fibers, and glass powder; color pigments such as titanium dioxide, carbon black, yellow lead, cadmium yellow, ochre, titanium yellow, zinc chromate, red iron oxide, aluminosilicate, quinacridone-based, phthalocyanine-based, anthroquinone-based, diketopyrrolopyrrole-based, benzimidazolone-based, and isoindolinone-based; and metallic pigments such as aluminum flakes, copper flakes, micaceous iron oxide, mica, and scaly powder of mica coated with a metal oxide.

[0048] The non-aqueous coating composition of the present invention does not necessarily need to contain a filler, but from the viewpoint of achieving the purpose of adding the filler, the content of the filler in the non-aqueous coating composition is preferably 0.001 to 80 mass %.

[0049] (Other Additives) The non-aqueous coating composition of the present invention may contain other substances, such as dehydrating agents (e.g., silane coupling agents), adhesion improvers, surfactants, curing catalysts, plasticizers, film-forming aids, driers, antifouling agents, sensitizers, antioxidants, light stabilizers, ultraviolet absorbers, water-resistant agents, antiseptic and antifungal agents, antifoaming agents, leveling agents, dispersants, flame retardants, antistatic agents, release agents, deodorizers, fragrances, and the like, to the extent that the properties of the non-aqueous coating composition of the present invention and the objects of the present invention are not impaired.

[0050] (Method for producing non-aqueous coating composition) The method for producing the non-aqueous coating composition of the present invention is not particularly limited, but the viscosity modifier consisting of a fatty acid diamide may be added to the resin in advance, and the resulting homogeneous dispersion may be blended with the remaining raw materials, or may be added and mixed together with various additives, solvents, and resins when preparing the non-aqueous coating composition. If the viscosity modifier is not sufficiently dispersed in the non-aqueous coating composition, the effects of the present invention may not be fully exhibited.

[0051] (Method of using non-aqueous coating composition) The non-aqueous coating composition of the present invention can be used in the form of a dispersion, or it can be used as a dried powdery non-aqueous coating composition after removing liquid components such as the solvent from the dispersion by drying treatment or the like.

[0052] The non-aqueous coating composition of the present invention can be applied to the surface of various substrates to a desired film thickness by known coating methods, such as roller coating, brush coating, air spraying, airless spraying, electrostatic coating, etc. Furthermore, by curing the non-aqueous coating composition applied to the surface of a substrate, a coated article having a coating film consisting of a cured product of the non-aqueous coating composition can be obtained.

[0053] Examples of the substrate include metal materials such as iron, aluminum, brass, copper, stainless steel, tinplate, zinc-plated steel, zinc alloys (Zn—Al, Zn—Ni, Zn—Fe, etc.), and plated steel; plastic materials such as resins such as polyethylene resin, polypropylene resin, acrylonitrile-butadiene-styrene (ABS) resin, polyamide resin, acrylic resin, vinylidene chloride resin, polycarbonate resin, polyurethane resin, and epoxy resin, and various FRPs; and inorganic materials such as glass, cement, and concrete, which may be surface-treated or the like.

[0054] (Uses of non-aqueous coating composition) The non-aqueous coating composition of the present invention can be used, for example, as a marine paint or an anticorrosion paint, but is not limited to these uses and can be used in various uses to which non-aqueous coatings are generally applicable.

[0055] While the preferred embodiments of the present invention have been described above, the present invention is not limited to the above-described embodiments. In other words, it is understood that other embodiments or various modifications that can be conceived by a person skilled in the art within the scope of the invention described in the claims also fall within the technical scope of the present invention.

[0056] The present invention will be specifically described below with reference to examples. However, the present invention is not limited to these examples. In the examples, "%" and "parts" refer to "% by mass" and "parts by mass" unless otherwise specified.

[0057] (Synthesis of fatty acid diamide) The diamine component and monocarboxylic acid component shown in Table 1 were added as raw materials to a four-neck flask in the molar ratios shown in Table 1, and the mixture was reacted at 190°C for 6 hours under a nitrogen gas stream while removing the generated water, to obtain fatty acid diamides of Synthesis Examples E1 to E2 and C1 to C4.

[0058]

[0059] (Production of viscosity modifier) ​​Next, the fatty acid diamides of Synthesis Examples E1 to E2 and C1 to C4 were each pulverized in a pulverizer to a median diameter of 1 μm to 10 μm, thereby obtaining viscosity modifiers of Production Examples 1 and 2 and Comparative Production Examples 1 to 4.

[0060] [Experimental Example 1: Solvent-free paint formulation] This experiment was an experiment in which the viscosity-imparting effect and sagging prevention properties were evaluated when the non-aqueous paint composition was a solvent-free paint.

[0061] (Production of non-aqueous coating compositions) Using the viscosity modifiers of Production Examples 1 and 2 and Comparative Production Examples 1 to 4 obtained as described above, non-aqueous coating compositions of Examples 1 and 2 and Comparative Examples 1 to 4 were produced according to formulation α shown in Table 2 or formulation β shown in Table 2.

[0062] <Example 1, Comparative Examples 1 to 3> For Example 1 and Comparative Examples 1 and 2, as shown in Table 2, 39.2 parts of jER (registered trademark) 806 (an epoxy resin manufactured by Mitsubishi Chemical Corporation) was used as the resin, and LS-632 (a reactive diluent manufactured by Hubei Greenhome Materials) was used. A mixture of 11.3 parts of a bifunctional reactive diluent manufactured by JNC Technology Co., Ltd., 2.3 parts of Sila-Ace (registered trademark) S510 (a silane coupling agent manufactured by JNC Corporation), 8.8 parts of Talc No. 1 (a body pigment manufactured by Takehara Chemical Industry Co., Ltd.), 15.0 parts of PG-K10 (a body pigment manufactured by Sibelco Japan), 22.1 parts of barium sulfate BA (a body pigment manufactured by Sakai Chemical Industry Co., Ltd.), and 1.3 parts of Typeque (registered trademark) R-820 (a rutile-type titanium oxide manufactured by Ishihara Sangyo Kaisha, Ltd.), and 1.5 parts of a viscosity modifier was added, and the mixture was dispersed in a 60°C constant temperature water bath using a dissolver (blade diameter 5 cm) for 10 minutes to obtain an epoxy base resin (Part A). To this base resin, 21.5 parts of Ancamine 2644 (an amine-based curing agent manufactured by Evonik Japan Co., Ltd.) was added as a curing agent (Part B), and the mixture was mixed to obtain the nonaqueous coating compositions of Example 1 and Comparative Examples 1 and 2. Furthermore, a nonaqueous coating composition of Comparative Example 3 was obtained in the same manner as in Example 1, except that no viscosity modifier was included. The viscosity modifiers and coating formulations used in Example 1 and Comparative Examples 1 to 3 are shown in Table 4.

[0063] <Example 2 and Comparative Examples 4 to 6> For Example 2 and Comparative Examples 4 to 5, as shown in Table 3, 39.2 parts of jER (registered trademark) 806 (an epoxy resin manufactured by Mitsubishi Chemical Corporation) was used as the resin, and LS-AGE (a reactive diluent manufactured by Hubei Greenhome Materials) was used. A mixture of 11.3 parts of a monofunctional reactive diluent manufactured by JNC Technology Co., Ltd., 2.3 parts of Sila-Ace (registered trademark) S510 (a silane coupling agent manufactured by JNC Corporation), 8.8 parts of Talc No. 1 (a body pigment manufactured by Takehara Chemical Industry Co., Ltd.), 15.0 parts of PG-K10 (a body pigment manufactured by Sibelco Japan), 22.1 parts of barium sulfate BA (a body pigment manufactured by Sakai Chemical Industry Co., Ltd.), and 1.3 parts of Typeque (registered trademark) R-820 (a rutile-type titanium oxide manufactured by Ishihara Sangyo Kaisha, Ltd.), and 1.5 parts of a viscosity modifier was added, and the mixture was dispersed in a 60°C constant temperature water bath using a dissolver (blade diameter 5 cm) for 10 minutes to obtain an epoxy base resin (Part A). To this base resin, 19.0 parts of Ancamine 2644 (an amine-based curing agent manufactured by Evonik Japan Co., Ltd.) was added as a curing agent (Part B), and the mixture was mixed to obtain the nonaqueous coating compositions of Example 2 and Comparative Examples 4 and 5. Furthermore, the nonaqueous coating composition of Comparative Example 6 was obtained in the same manner as in Example 2, except that no viscosity modifier was included. The viscosity modifiers and coating formulations used in Example 2 and Comparative Examples 4 to 6 are shown in Table 5.

[0064]

[0065]

[0066]

[0067]

[0068] (Evaluation Method) The non-aqueous coating compositions of Examples 1 and 2 and Comparative Examples 1 to 6 obtained as described above were evaluated for viscosity imparting effect and anti-sagging property as follows.

[0069] <Evaluation of viscosity-imparting effect> The day after the non-aqueous coating compositions were prepared as described above, the viscosity (P) was measured at 25°C and 60 rpm using a Brookfield viscometer. These results are shown in Tables 4 and 5. Note that the higher the viscosity of the non-aqueous coating composition, the greater the viscosity-imparting effect of the viscosity modifier.

[0070] <Evaluation of sagging prevention properties> As an index of sagging prevention properties, the sagging limit film thickness of the non-aqueous coating composition prepared as described above was measured. Specifically, using a sag tester (trade name "Sag Tester BOX 100-500, 600-1000, 800 μm to 1200, 1100-1500, 1200-1600 or 1600-2000", a sagging tester manufactured by Taiyu Kizai Co., Ltd.), the non-aqueous coating composition of any of Examples 1 and 2 and Comparative Examples 1 to 6 was applied to sagging test paper (trade name "All Black Measurement Paper", manufactured by Taiyu Kizai Co., Ltd.) in five film thicknesses that differed by 100 μm in increments of 100 μm (100 μm to 500 μm, 600 μm to 1000 μm, 800 μm to 1200 μm, 1100 μm to 1500 μm, 1200 μm to 1600 μm or 1600 μm to 2000 μm). As a result, coating film strips of five different film thicknesses were arranged at predetermined intervals on the sagging test paper. Next, this test paper was stood upright with the thinner coating film strip at the top and air-dried at room temperature. After that, the thickness of the coating film strip with a thickness one step thinner than the coating film strip at which the paint first dripped over the gap between the coating film strips and contacted the lower coating film strip was observed was determined to be the sagging limit film thickness (μm). In this example, it was determined that a coating film with a sagging limit film thickness evaluated by the above method of 800 μm or more had sufficient sagging prevention properties to solve the problems of the present invention.

[0071] (Evaluation Results) The evaluation results of the viscosity imparting effect and sagging prevention property evaluated as described above are shown in Tables 4 and 5 above.

[0072] As shown in Tables 4 and 5, the nonaqueous coating compositions of Examples 1 and 2, which used 1,4-DAB as the diamine component, all showed significant differences in viscosity and critical film thickness before sagging compared with the nonaqueous coating compositions of Comparative Examples 1, 2, 4, and 5, which used diamines other than 1,4-DAB (EDA or HMDA) as the diamine component, and the nonaqueous coating compositions of Comparative Examples 3 and 6, which did not contain a viscosity modifier, and were therefore excellent in viscosity-imparting effect and sagging prevention.

[0073] [Experimental Example 2: Ultra-high solids paint formulation] This experiment was an experiment in which the viscosity-imparting effect and sagging prevention properties were evaluated when the non-aqueous paint composition was an ultra-high solids paint.

[0074] (Production of non-aqueous coating compositions) Using the viscosity modifiers of Production Examples 1 and 2 and Comparative Production Examples 1 and 3 obtained as described above, non-aqueous coating compositions of Examples 3 and 4 and Comparative Examples 7 and 9 were produced at the formulation γ shown in Table 6 or the formulation δ shown in Table 7.

[0075] <Example 3, Comparative Examples 7 and 8> For Example 3 and Comparative Examples 7 and 8, as shown in Table 6, 39.1 parts of jER (registered trademark) 806 (an epoxy resin manufactured by Mitsubishi Chemical Corporation) was used as the resin, and LS-632 (manufactured by Hubei Greenhome Materials) was used as the reactive diluent. A mixture of 11.3 parts of a bifunctional reactive diluent manufactured by JNC Technology Co., Ltd., 2.3 parts of Sila-Ace (registered trademark) S510 (a silane coupling agent manufactured by JNC Corporation), 2.0 parts of dimethyl carbonate as an organic solvent, 8.8 parts of Talc No. 1 (a body pigment manufactured by Takehara Chemical Industry Co., Ltd.), 15.0 parts of PG-K10 (a body pigment manufactured by Sibelco Japan Co., Ltd.), 22.1 parts of barium sulfate BA (a body pigment manufactured by Sakai Chemical Industry Co., Ltd.), and 1.3 parts of Typepaque (registered trademark) R-820 (a rutile-type titanium oxide manufactured by Ishihara Sangyo Kaisha, Ltd.), and 1.0 parts of a viscosity modifier was charged and dispersed for 10 minutes in a 60 ° C. constant temperature water bath using a dissolver (blade diameter 5 cm) to obtain an epoxy base resin (PART A). To this base resin, 21.5 parts of Ancamine 2644 (an amine-based curing agent manufactured by Evonik Japan Co., Ltd.) and 9.1 parts of xylene were added as PART B and mixed to obtain the nonaqueous coating compositions of Example 3 and Comparative Example 7. Furthermore, a nonaqueous coating composition of Comparative Example 8 was obtained in the same manner as Example 3 except that no viscosity modifier was contained. The viscosity modifiers and coating formulations used in Example 3 and Comparative Examples 7 and 8 are shown in Table 8.

[0076] <Example 4 and Comparative Examples 9 to 10> For Example 4 and Comparative Examples 9 to 10, as shown in Table 7, 39.1 parts of jER (registered trademark) 806 (an epoxy resin manufactured by Mitsubishi Chemical Corporation) was used as the resin, and LS-632 (a reactive diluent manufactured by Hubei Greenhome Materials) was used. A mixture of 11.3 parts of a bifunctional reactive diluent manufactured by JNC Technology Co., Ltd., 2.3 parts of Sila-Ace (registered trademark) S510 (a silane coupling agent manufactured by JNC Corporation), 2.0 parts of dimethyl carbonate as an organic solvent, 8.8 parts of Talc No. 1 (a body pigment manufactured by Takehara Chemical Industry Co., Ltd.), 15.0 parts of PG-K10 (a body pigment manufactured by Sibelco Japan Co., Ltd.), 22.1 parts of barium sulfate BA (a body pigment manufactured by Sakai Chemical Industry Co., Ltd.), and 1.3 parts of Typepaque (registered trademark) R-820 (a rutile-type titanium oxide manufactured by Ishihara Sangyo Kaisha, Ltd.), and 1.0 parts of a viscosity modifier was charged and dispersed for 10 minutes in a 60 ° C. constant temperature water bath using a dissolver (blade diameter 5 cm) to obtain an epoxy base resin (PART A). To this base resin, 19.0 parts of Ancamine 2644 (an amine-based curing agent manufactured by Evonik Japan Co., Ltd.) and 9.1 parts of xylene were added as PART B and mixed to obtain the nonaqueous coating compositions of Example 4 and Comparative Example 9. Furthermore, a nonaqueous coating composition of Comparative Example 10 was obtained in the same manner as in Example 4 except that no viscosity modifier was contained. The viscosity modifiers and coating formulations used in Example 4 and Comparative Examples 9 and 10 are shown in Table 9.

[0077]

[0078]

[0079]

[0080]

[0081] (Evaluation Method) The non-aqueous coating compositions of Examples 3 and 4 and Comparative Examples 7 to 10 obtained as described above were evaluated for viscosity imparting effect and anti-sagging property in the same manner as in Experimental Example 1.

[0082] (Evaluation Results) The evaluation results of the viscosity imparting effect and anti-sagging property evaluated as described above are shown in Tables 8 and 9 above.

[0083] As shown in Tables 8 and 9, the nonaqueous coating compositions of Examples 3 and 4, which used 1,4-DAB as the diamine component, all showed significant differences in viscosity and sagging limit film thickness compared to the nonaqueous coating compositions of Comparative Examples 7 and 9, which used a diamine other than 1,4-DAB (EDA) as the diamine component, and the nonaqueous coating compositions of Comparative Examples 8 and 10, which did not contain a viscosity modifier, and were therefore excellent in viscosity-imparting effect and sagging prevention.

Claims

1. A viscosity modifier for non-aqueous paints comprising a fatty acid diamide obtained by subjecting a diamine component and a monocarboxylic acid component to a condensation reaction, wherein the diamine component is 1,4-diaminobutane, and the non-aqueous paint is a solventless paint or an ultra-high solid paint.

2. The viscosity modifier for non-aqueous paints according to claim 1, wherein the monocarboxylic acid component is a mixture of hydrogenated castor oil fatty acid and a linear saturated fatty acid.

3. The viscosity modifier for non-aqueous paints according to claim 2, wherein the linear saturated fatty acid has 8 to 10 carbon atoms.

4. The viscosity modifier for non-aqueous paints according to claim 1, wherein the monocarboxylic acid component contains a linear saturated fatty acid having 8 to 10 carbon atoms.

5. A non-aqueous paint composition containing a viscosity modifier and a resin, wherein the viscosity modifier is composed of a fatty acid diamide obtained by subjecting a diamine component and a monocarboxylic acid component to a condensation reaction, the diamine component is 1,4-diaminobutane, and the non-aqueous paint composition is a solventless paint or an ultra-high solid paint.

6. The non-aqueous paint composition according to claim 5, wherein the monocarboxylic acid component is a mixture of hydrogenated castor oil fatty acid and a linear saturated fatty acid.

7. The non-aqueous paint composition according to claim 6, wherein the linear saturated fatty acid has 8 to 10 carbon atoms.

8. The non-aqueous paint composition according to claim 5, wherein the monocarboxylic acid component contains a linear saturated fatty acid having 8 to 10 carbon atoms.

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