Coating agent composition and its use

Abstract

This invention provides a coating agent composition using a non-fluorine compound that can provide a coating film with excellent adhesion to the substrate and water repellency. [Solution] A coating agent composition comprising (A), a glyceride compound containing one or more reactive functional groups represented by, for example, formulas (18) to (21) below, and (B), a diluent, wherein the content of (B) is 1 part by weight or more and 100,000 parts by weight or less per 100 parts by weight of (A). JPEG2026059746000015.jpg34140

Description

[Technical Field]

[0001] This invention relates to a coating agent composition and its use. [Background technology]

[0002] Traditionally, water-repellent and oil-repellent coatings have primarily used fluorine-containing compounds as their main component due to their low surface energy.

[0003] On the other hand, in recent years, the harmful effects of PFAS substances have become a concern, and from the perspective of environmental considerations, the development of water-repellent and oil-repellent coating agents using fluorine-free compounds that do not contain fluorine-containing compounds is progressing (for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2023-525299 [Overview of the project] [Problems that the invention aims to solve]

[0005] In their research on coating agents, the inventors discovered that (a) coating agents using fluorine-containing compounds have a problem in addition to the previously known environmental impact issues, namely, insufficient adhesion between the resulting coating film and the substrate. Furthermore, they found that (b) coating agents using non-fluorine compounds have room for improvement in terms of the adhesion of the resulting coating film to the substrate and its water repellency.

[0006] Given the circumstances described above, the object of the present invention is to provide a coating agent composition using a non-fluorine compound that can provide a coating film with excellent adhesion to a substrate and water repellency. [Means for solving the problem]

[0007] As a result of diligent research to provide the above-described coating agent composition, the present inventors have discovered that a coating agent composition comprising a glyceride compound containing a reactive functional group having a specific structure and a diluent can provide a coating film with excellent adhesion to the substrate and water repellency, even though it is a coating agent composition using a non-fluorine compound, and have thus completed the present invention.

[0008] In other words, one aspect of the present invention includes the following configuration.

[0009] [1] A coating composition comprising: (A) a glyceride compound containing one or more reactive functional groups represented by the following general formulas (1) to (4) and (14) to (17); and (B) a diluent, wherein the content of (B) is 1 part by weight or more and 100,000 parts by weight or less per 100 parts by weight of (A):

[0010] [ka]

[0011] (In the above equations (1) to (4) and (14) to (17), R 1 From R 6 and R 9 From R 14 Each of these independently represents a single bond or a divalent organic group, R 15 From R 18 Each of these independently represents an alkyl group having 1 to 5 carbon atoms, and R 19 From R 30 Each of these independently represents an alkylene group having 1 to 5 carbon atoms, X represents one selected from the group consisting of hydrolyzable silyl groups, (meth)acryloyl groups, and epoxy groups, and FA represents a fatty acid. [2] The coating agent composition according to [1], further comprising a curing catalyst which is component (C), wherein the content of component (C) relative to 100 parts by weight of component (A) is 0.01 parts by weight or more and 100 parts by weight or less. [3] The coating composition according to [1] or [2], further comprising an adhesion promoter which is component (D), wherein the content of component (D) is 0.01 to 100 parts by weight relative to 100 parts by weight of component (A). A coating film obtained by curing a coating agent composition described in any one of [4] [1] to [3]. [Effects of the Invention]

[0012] According to one embodiment of the present invention, a coating agent composition using a non-fluorine compound can be provided that can provide a coating film with excellent adhesion to a substrate and water repellency. [Modes for carrying out the invention]

[0013] One embodiment of the present invention is described below, but the present invention is not limited thereto.

[0014] The present invention is not limited to the configurations described below, and various modifications are possible within the scope of the claims.

[0015] Furthermore, embodiments or examples obtained by combining the technical means disclosed in different embodiments or examples are also included within the technical scope of the present invention.

[0016] Furthermore, by combining the technical means disclosed in each embodiment, new technical features can be formed.

[0017] Furthermore, all academic and patent documents cited herein are incorporated as references within this specification.

[0018] [1. Technical concept of the present invention] Traditionally, water-repellent and oil-repellent coating compositions have used fluorine-containing compounds such as fluororesins due to their low surface energy. However, in recent years, the harmful effects of PFAS substances have been recognized, and regulations are being imposed on the use of fluorine-containing compounds. Therefore, there is a need for new water-repellent materials that do not contain fluorine-containing compounds.

[0019] Various compounds have been proposed as new water-repellent materials that do not contain fluorine-containing compounds, but these have not been sufficient in terms of adhesion to the substrate and water repellency of the resulting coating film.

[0020] In light of the above circumstances, the present inventors diligently conducted research with the aim of providing a coating agent composition using a non-fluorine compound that can provide a coating film with excellent adhesion to the substrate and water repellency. As a result, they discovered that by using a glyceride compound containing a reactive functional group having a specific structure as a water-repellent material, it is possible to provide a coating film with excellent adhesion to the substrate and water repellency, thus completing the present invention.

[0021] Furthermore, the inventors have discovered that, surprisingly, the coating composition according to the above embodiment of the present invention, despite being a coating composition containing a non-fluorine-based compound, exhibits superior adhesion to the substrate compared to coating compositions using fluorine-containing compounds. In other words, the coating composition according to the present embodiment of the present invention can solve a novel problem—"improving adhesion to the substrate"—which could not be solved by conventional coating compositions containing non-fluorine-based compounds, nor by coating compositions using fluorine-containing compounds.

[0022] Furthermore, in the course of the above investigation, the inventors found that coating agent compositions using fluorine-containing compounds have room for improvement in terms of durability, and that a coating agent composition according to one embodiment of the present invention can also solve the durability-related problems described above.

[0023] As described above, the coating agent composition according to one embodiment of the present invention is a coating agent composition with low environmental impact using a non-fluorine-based compound, and can provide a coating film excellent in adhesion to a substrate and water repellency, and thus is also excellent in durability. Therefore, the coating agent composition according to one embodiment of the present invention can be suitably used as a novel coating agent composition.

[0024] 〔2. Coating agent composition〕 The coating agent composition according to one embodiment of the present invention contains (A) any one or more reactive functional group-containing glyceride compounds represented by the following general formulas (1) to (4) and (14) to (17), and (B) a diluent, and is a coating agent composition in which the content of the (B) component with respect to 100 parts by weight of the (A) component is 1 part by weight or more and 100,000 parts by weight or less:

[0025]

Chemical formula

[0026] (In the above formulas (1) to (4) and (14) to (17), R 1 to R 6 and R 9 to R 14 each independently represents a single bond or a divalent organic group, R 15 to R 18 each independently represents an alkyl group having 1 to 5 carbon atoms, R 19 to R 30 each independently represents an alkylene group having 1 to 5 carbon atoms, X represents one selected from the group consisting of a hydrolyzable silyl group, a (meth)acryloyl group, and an epoxy group, and FA represents a fatty acid.).

[0027] In this specification, the "coating agent composition according to one embodiment of the present invention" may be referred to as "this composition".

[0028] Because this composition has the aforementioned structure, it is an environmentally friendly coating agent composition using non-fluorine compounds, yet it can provide a coating film with excellent adhesion to the substrate and water repellency. It also has the advantage of providing a coating film with excellent durability. In addition, the resulting coating film also has the advantage of excellent writability and peelability.

[0029] In this specification, the adhesion, water repellency, durability, writability, and peelability of the coating film obtained by curing the coating agent composition to the substrate are measured or evaluated by the method described in the examples.

[0030] <(A) Component: Reactive functional group-containing glyceride compound> This composition contains, as component (A), one or more reactive functional group-containing glyceride compounds represented by the following general formulas (1) to (4) and (14) to (17).

[0031] [ka]

[0032] (In the above equations (1) to (4) and (14) to (17), R 1 From R 6 and R 9 From R 14 Each of these independently represents a single bond or a divalent organic group, R 15 From R 18 Each of these independently represents an alkyl group having 1 to 5 carbon atoms, and R 19 From R 30 Each of these independently represents an alkylene group having 1 to 5 carbon atoms, X represents one selected from the group consisting of hydrolyzable silyl groups, (meth)acryloyl groups, and epoxy groups, and FA represents a fatty acid.

[0033] (R 1 From R 6 ) In equations (1) to (4) and (14) to (17), R 1 From R 6 and R9 From R 14 It is not particularly limited as long as it is a single bond or a divalent organic group. 1 From R 6 Examples of divalent organic groups include alkylene groups, alkenylene groups, alkynylene groups, or arylene groups, and these groups may contain heteroatoms.

[0034] In equations (1) to (4) and (14) to (17), R 1 From R 6 and R 9 From R 14 Each of these may independently be an ester bond, an ether bond, an amide bond, a urethane bond, a thioether bond, a carbonate bond, a urea bond, or a divalent hydrocarbon group having 2 or more carbon atoms which may have a heteroatom, or a group containing these.

[0035] Of these, from the viewpoint of ease of manufacture of component (A), R 1 From R 6 and R 9 From R 14 Each of these preferably independently has an ester bond, an ether bond, a urethane bond, or a carbonate bond, more preferably an ester bond, a urethane bond, or a carbonate bond, and even more preferably a urethane bond or a carbonate bond.

[0036] In equations (14) to (17), R 15 From R 18 Each of these independently represents an alkyl group having 1 to 5 carbon atoms, and preferably an alkyl group having 2 carbon atoms (i.e., an ethyl group). Compounds of formulas (14) to (17) having this configuration (especially compounds containing a (meth)acryloyl group) have the advantage that the materials used in their manufacture are readily available, meaning that the compounds are readily available.

[0037] In equation (14), R 19 From R 21They may be the same or different, but it is preferable that they be the same. 19 From R 21 Compounds of formula (14) that have the same group (especially compounds containing a (meth)acryloyl group) have the advantage that the materials used in their manufacture are readily available, i.e., the compounds are readily available.

[0038] In equation (15), R 22 From R 24 They may be the same or different, but it is preferable that they be the same. 22 From R 24 Compounds of formula (15) that have the same group (especially compounds containing a (meth)acryloyl group) have the advantage that the materials used in their manufacture are readily available, i.e., the compounds are readily available.

[0039] In equation (16), R 25 From R 27 They may be the same or different, but it is preferable that they be the same. 25 From R 27 Compounds of formula (16) that share the same group (particularly compounds containing a (meth)acryloyl group) have the advantage that the materials used in their manufacture are readily available, i.e., the compounds are readily available.

[0040] In equation (17), R 28 From R 30 They may be the same or different, but it is preferable that they be the same. 28 From R 30 Compounds of formula (17) that share the same group (particularly compounds containing a (meth)acryloyl group) have the advantage that the materials used in their manufacture are readily available, i.e., the compounds are readily available.

[0041] Because the compounds are readily available, (i) In equation (14), R 15 is a C2 alkyl group (i.e., an ethyl group), and R 19 From R 21It is particularly preferable that all of them are alkylene groups (i.e., methylene groups) having 1 carbon atom. (ii) In equation (15), R 16 is a C2 alkyl group (i.e., an ethyl group), and R 22 From R 24 It is particularly preferable that all of them are alkylene groups (i.e., methylene groups) having 1 carbon atom. (iii) In equation (16), R 17 is a C2 alkyl group (i.e., an ethyl group), and R 25 From R 27 It is particularly preferable that all of them are alkylene groups (i.e., methylene groups) having 1 carbon atom. (iv) In equation (17), R 18 is a C2 alkyl group (i.e., an ethyl group), and R 28 From R 30 It is particularly preferable that all of them are alkylene groups (i.e., methylene groups) having 1 carbon atom. In other words, it is particularly preferable that the compounds of formulas (14) to (17) are compounds represented by the following formulas (18) to (21).

[0042] [ka]

[0043] (X) In formulas (1) to (4) and (14) to (17), X is selected from the group consisting of hydrolyzable silyl groups, (meth)acryloyl groups, and epoxy groups.

[0044] • Hydrolyzable silyl groups The structure of the hydrolyzable silyl group X is not particularly limited. A hydrolyzable silyl group commonly used in the art may be used.

[0045] In one embodiment, in formulas (1) to (4) and (14) to (17), the hydrolyzable silyl group X is represented by the following general formula (5).

[0046] -Si(R 7 ) 3-a (Y) a (5) (In the formula, R 7 Each of the following independently represents a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may contain a heteroatom. Each of the following independently represents a hydroxyl group or a hydrolyzable group. (a represents a natural number between 1 and 3).

[0047] Multiple R groups within a single hydrolyzable silyl group 7 When R exists, 7 The structures may be identical or different.

[0048] R 7 Examples include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, and aralkyl groups having 7 to 20 carbon atoms.

[0049] Y represents a hydroxyl group or a hydrolyzable group. Examples of hydrolyzable groups include hydroxyl groups, halogen groups, alkoxy groups, aryloxy groups, acyloxy groups, ketoximate groups, amino groups, amide groups, acid amide groups, aminooxy groups, oxime groups, mercapto groups, alkenyloxy groups, perfluoroalkyloxy groups, polyfluoroalkyloxy groups, perfluoroaryloxy groups, polyfluoroaryloxy groups, etc.

[0050] Among these, alkoxy groups such as methoxy and ethoxy groups are more preferred due to their mild hydrolysis, ease of handling, and high availability, with methoxy and ethoxy groups being even more preferred, and methoxy groups being particularly preferred.

[0051] Generally, alkoxy groups tend to be more reactive the fewer carbon atoms they have. That is, the reactivity decreases in the order of methoxy, ethoxy, and propoxy groups. This property can be used to appropriately determine the specific structure of the hydrolyzable silyl group depending on the manufacturing method or application of component (A).

[0052] a is a natural number between 1 and 3. From the viewpoint that a coating film can be easily obtained by forming a network structure through condensation, a is preferably 2 or 3.

[0053] Specific examples of hydrolyzable silyl groups include trialkoxysilyl groups such as trimethoxysilyl, triethoxysilyl, and triisopropoxysilyl; methyldialkoxysilyl groups such as methyldimethoxysilyl, methyldiethoxysilyl, and methyldiisopropoxysilyl; and (chloromethyl)dimethoxysilyl, (methoxymethyl)dimethoxysilyl, vinyldimethoxysilyl, and vinyldiethoxysilyl.

[0054] From the viewpoint of the physical properties of the resulting coating film and the availability and ease of handling of the raw material compounds, the hydrolyzable silyl group is preferably a methyldialkoxysilyl group or a trialkoxysilyl group. From the viewpoint of the ease of handling of this composition and the flexibility of the resulting coating film, the hydrolyzable silyl group is preferably a methyldialkoxysilyl group. From the viewpoint of a fast curing rate, the hydrolyzable silyl group is preferably a trialkoxysilyl group.

[0055] Specifically, preferred methyldialkoxysilyl groups are methyldimethoxysilyl groups and methyldiethoxysilyl groups. Preferred trialkoxysilyl groups are trimethoxysilyl groups and triethoxysilyl groups.

[0056] (meth)acryloyl group In this specification, "(meth)acryloyl group" means acryloyl group and methacryloyl group, and X being a (meth)acryloyl group means that X is selected from acryloyl group and methacryloyl group.

[0057] In one embodiment, there are no particular restrictions on the (meth)acryloyl group X in formulas (1) to (4) and (14) to (17), and a (meth)acryloyl group commonly used in the art may be used. However, it is preferable that the group is represented by the following formula (6) because the resulting coating film has excellent physical properties, the raw materials are readily available, and it is easy to manufacture.

[0058] [ka]

[0059] (In formula (6), R 8 (where represents a hydrogen atom or a methyl group).

[0060] R 8 If is a hydrogen atom, the group represented by formula (6) becomes an acryloyl group, and R 8 If is a methyl group, the group represented by formula (6) becomes a methacryloyl group. Depending on the desired physical properties of the resulting coating film, an acryloyl group or a methacryloyl group can be arbitrarily selected as the (meth)acryloyl group constituting X.

[0061] For example, if good rapid curing properties, easy availability of raw materials, cost-effectiveness, and reactivity with other components are important, then the (meth)acryloyl group constituting X may be R 8 In some cases, it is preferable to select an acryloyl group in which the hydrogen atom is present. On the other hand, if durability of the coating film is important, the (meth)acryloyl group of component (A) may be R 8 It may be preferable to select a methacryloyl group which is a methyl group. Also, if it is found to be preferable to mix the two during the course of research, the two may be used in combination. In this composition, component (A) is R 8 An acryloyl group-containing glyceride compound having an acryloyl group with a hydrogen atom as the X group, and R 8 It may also be a mixture (aggregate) of a methacryloyl group-containing glyceride compound having a methacryloyl group, which is a methyl group, as the X group.

[0062] • Epoxy group The epoxy group X is not particularly limited, and any epoxy group commonly used in the art may be used. In one embodiment, the epoxy group X is preferably one or more epoxy groups represented by the following formulas (7) to (9) because the resulting coating film has excellent physical properties, the raw materials are readily available, and it is easy to manufacture.

[0063] [ka]

[0064] Component (A) may be a mixture (aggregate) of an epoxy group-containing glyceride compound containing an epoxy group represented by formulas (7) to (9) above, and an epoxy group-containing glyceride compound containing an epoxy group other than the epoxy group represented by formulas (7) to (9) above.

[0065] (FA) The fatty acid FA of component (A) is not particularly limited, but is preferably one or more selected from the group consisting of stearic acid, (meth)acrylic acid, palmitic acid, acetic acid, butyric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosenoic acid, erucic acid, conjugated linoleic acid, punicic acid, eleostearic acid, ricinoleic acid, hydroxystearic acid, epoxidized fatty acids, eicosapentaenoic acid, 12-hydroxystearic acid, glycolic acid, 16-hydroxyhexadecanoic acid, 15-hydroxypentadecanoic acid, 2-hydroxypalmitic acid, lactic acid, 3-hydroxybutanoic acid, docosahexaenoic acid, and trans fatty acids produced by partial hydrogenation of these. If FA has these structures, it has the advantage of being easy to obtain raw materials and easy to manufacture component (A).

[0066] Among these, since it is inexpensive and easily available, it is more preferable that the FA of the component (A) is at least one selected from the group consisting of stearic acid, palmitic acid, acetic acid, lauric acid, oleic acid, and 12-hydroxystearic acid.

[0067] When the FA of the component (A) has a hydroxy group, a hydrolyzable silyl group may be introduced into a part or all of the hydroxy groups.

[0068] From the viewpoints of the reactivity, ease of production, and availability of the component (A), it is particularly preferable that the hydrolyzable silyl group-containing moiety and glycerin in the component (A) are bonded by a urethane bond. In other words, it is preferable that the component (A) has a structure represented by the following general formulas (10) to (13).

[0069]

Chemical formula

[0070] (In the above formulas (10) to (13), X and FA are the same as those in formulas (1) to (4), and R 1a to R 6a each independently represents a single bond or a divalent organic group.).

[0071] In formulas (10) to (13), R 1a to R 6a are not particularly limited. R 1a to R 6a may be the same as or different from R 1 to R 6 Among these, from the viewpoints of ease of synthesis and availability of raw materials, it is preferable that R 1a to R 6a are each independently a single bond, an alkylene group, or an arylene group, and more preferably a single bond or an alkylene group.

[0072] In formulas (10) to (13), R [[ID=S49]] 1a to R 6aFrom the viewpoint of ease of synthesis and availability of raw materials, it is preferable that each of them be one or more selected from the group consisting of a single bond, methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group, heprene group, octylene group, nonylene group, and decylene group; more preferably one or more selected from the group consisting of a single bond, methylene group, ethylene group, propylene group, butylene group, pentylene group, and hexylene group; and even more preferably one or more selected from the group consisting of a single bond, methylene group, ethylene group, and propylene group.

[0073] (A) The component may consist of one or more compounds used individually, or it may consist of two or more compounds with different chemical formulas used in combination.

[0074] The content of component (A) in this composition is not particularly limited, but since it has the advantage of being a composition with excellent adhesion to the substrate and water repellency, it is preferably 1% by weight or more and 20% by weight or less, and more preferably 5% by weight or more and 10% by weight or less, of 100% by weight of the total amount of this composition.

[0075] The method for producing component (A) is not particularly limited, but for example, component (A) having a hydrolyzable silyl group as the reactive functional group X can be produced by introducing a hydrolyzable silyl group to a monoglyceride or diglyceride to which the target fatty acid is bonded by any of the reactions (i) to (v) below. Component (A) having a (meth)acryloyl group as the reactive functional group X can be produced by any of the reactions (vi) to (viii) below. Furthermore, component (A) having an epoxy group as the reactive functional group X can be produced by introducing an epoxy group to a monoglyceride or diglyceride to which the target fatty acid is bonded by any of the reactions (ix) to (xiii) below.

[0076] (i) A method for adding a compound having a hydrolyzable silyl group and an isocyanate group (preferably carried out under a tin catalyst or bismuth catalyst from the viewpoint of reaction rate). (ii) A method for condensing a compound having a hydrolyzable silyl group and an acid halide group (it is preferable to carry out the reaction in the presence of a basic substance such as an amine). (iii) A method for condensing a hydrolyzable silyl group with a compound having an aryl orthoformate skeleton or a chloroformate skeleton (preferably carried out in the presence of a basic substance such as an amine). (iv) A method of condensing a hydrolyzable silyl group with a halogen group, or a compound having a group generally called a leaving group, such as a tosyloxy group (it is preferable to carry out the reaction in the presence of a basic substance). (v) A method for condensing a compound having a hydrolyzable silyl group and a hydroxyl group (it is preferable to carry out the reaction in the presence of a substance that promotes the condensation reaction). (vi) A method of reacting a monoglyceride or diglyceride to which a target fatty acid is bound with an acylating agent (for example, methacrylic chloride or methacrylic anhydride, or acrylic chloride or acrylic anhydride, etc.) (vii) A method for producing triglycerides, which are formed by chemical or enzymatic transesterification of glyceride acrylate or glyceride methacrylate bonded to a fatty acid of the choice, followed by separation and purification as necessary. (viii) A method of chemically or enzymatically transesterifying a triglyceride to which a target fatty acid is bound with a methacrylic acid ester or acrylic acid ester, such as methyl (meth)acrylate or ethyl (meth)acrylate, and separating and purifying it as necessary. (ix) A method for adding a compound having an epoxy group and an isocyanate group (preferably carried out under a tin catalyst or bismuth catalyst from the viewpoint of reaction rate). (x) A method for condensing a compound having an epoxy group and an acid halide group (preferably carried out in the presence of a basic substance such as an amine). (xi) A method for condensing a compound having an epoxy group and an aryl orthoformate skeleton or a chloroformate skeleton (preferably carried out in the presence of a basic substance such as an amine). (xii) A method for condensing a compound having an epoxy group and a halogen group, or a group generally called a leaving group, such as a tosyloxy group (it is preferable to carry out the reaction in the presence of a basic substance). (xiii) A method for condensing a compound having an epoxy group and a hydroxyl group (it is preferable to carry out the reaction in the presence of a substance that promotes the condensation reaction). As is clear from the example of the manufacturing method for component (A) described above, the reactive functional group-containing glyceride, which is component (A), can be manufactured using glyceride compounds, such as monoglycerides, diglycerides, and triglycerides, which are bio-based raw materials, as the main raw materials. Therefore, in addition to not containing fluorine-containing compounds, this composition can contribute to reducing environmental impact from the perspective of product sustainability in a sustainable society.

[0077] <(B) Component: Diluent> This composition contains a diluent as component (B). The diluent as component (B) is not particularly limited, and any diluent commonly used in the art can be used.

[0078] For example, as the diluent component (B), a third-class organic solvent such as gasoline, coal tar naphtha (including solvent naphtha), petroleum ether, petroleum naphtha, petroleum benzine, turpentine oil, or mineral spirits (including mineral thinner, petroleum spirit, white spirit, and mineral turpentine) can be used.

[0079] Furthermore, the diluent component (B) may include hydrocarbon solvents such as n-butane, n-hexane, n-heptane, n-octane, cyclopentane, cyclohexane, and cyclobutane; aromatic solvents such as toluene and xylene; ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, and propylene glycol monomethyl ether. Organic solvents other than Class 3 organic solvents can also be used, such as ether-based solvents like ether acetate, propylene glycol monoethyl ether acetate, and dioxane; ester-based solvents like methyl acetate, ethyl acetate, n-butyl acetate, isobutyl acetate, methyl acetoacetate, ethylene glycol monomethyl ether acetate, and butyl carbitol acetate; ketone-based solvents like acetone, acetylacetone, diacetone alcohol, methyl ethyl ketone, methyl isobutyl ketone, and diisobutyl ketone; and alcohol-based solvents like methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, isobutanol, and n-pentanol.

[0080] Furthermore, water or lower alcohols that are not mixed with component (A) can also be used as a diluent by emulsifying them. In addition, vegetable oils and animal oils that do not have functional groups, which may be present after the manufacture of component (A) represented by general formulas (1) to (4) and (14) to (17), can also be used as a diluent to the extent that they do not impair the effects of the present invention.

[0081] Among the various diluents mentioned above, organic solvents other than Class 3 organic solvents are preferred as the diluent for component (B) because they have excellent solubility with component (A), are highly volatile, allowing the paint to dry quickly, and have the advantage of readily available raw materials. Hydrocarbon solvents such as n-butane, n-hexane, n-heptane, n-octane, cyclopentane, cyclohexane, and cyclobutane are more preferred. Furthermore, if the use of solvents is problematic, water, vegetable oils, or animal oils are also suitable as diluents.

[0082] (B) As the diluent component, one of the above-mentioned Class 3 organic solvents or organic solvents other than Class 3 organic solvents may be used alone, or two or more may be used in mixture form.

[0083] The content of component (B) in this composition is 1 part by weight or more and 100,000 parts by weight or less per 100 parts by weight of component (A). Having component (B) within this range allows component (A) to be uniformly applied to the substrate (also called the adherend), dries quickly, making it easy to use, and also reduces environmental impact by not using excess solvent. While the content of component (B) in this composition is not particularly limited within the above range, the lower limit of the content of component (B) is preferably 10 parts by weight or more, more preferably 100 parts by weight or more, and even more preferably 500 parts by weight or more, per 100 parts by weight of component (A). The upper limit of the content of component (B) is preferably 10,000 parts by weight or less, more preferably 5,000 parts by weight or less, and even more preferably 2,000 parts by weight or less, per 100 parts by weight of component (A).

[0084] <(C) component: curing catalyst> The composition preferably contains a curing catalyst as component (C). The curing catalyst, which is component (C), catalyzes the reaction between the reactive functional groups of component (A), and is a component that can promote the curing of the composition, in other words, the formation of a coating film. That is, the composition has the advantage of being able to improve the curing speed by containing component (C). In addition, it is possible to further improve the water repellency and peelability of the coating film obtained by curing the composition.

[0085] Component (C) is preferably a catalyst that can catalyze the reaction between reactive functional groups, based on the type of reactive functional group present in component (A) of this composition.

[0086] For example, if the composition contains a reactive functional group-containing glyceride compound having a hydrolyzable silyl group as component (A), then various catalysts capable of catalyzing reactions between hydrolyzable silyl groups, such as organotin compounds, organobismuth compounds, metal carboxylate salts, amine compounds, carboxylic acids, and alkoxy metals, can be suitably used as component (C).

[0087] When the composition contains a reactive functional group-containing glyceride compound having a hydrolyzable silyl group as component (A), specific examples of component (C) include the compounds described in WO2023 / 162664

[0101] and subsequent editions by the same applicant. Among these, organotin compounds, metal carboxylate salts, mixtures of carboxylic acids and amine compounds, and alkoxy metals are preferred.

[0088] Examples of organotin compounds include dibutyltin dilaurate, dibutyltin dioctanoate, dibutyltin diversate, dibutyltin distearate, dibutyltin bis(butylmaleate), dibutyltin diacetate, dibutyltin oxide, dibutyltin di(acetylacetonate), dioctyltin bis(acetylacetonate), dioctyltin dilaurate, dioctyltin dioctanoate, dioctyltin diversate, dioctyltin distearate, dioctyltin diacetate, and dioctyltin oxide.

[0089] Examples of metal carboxylate salts include tin octylate, tin laurylate, tin neodecanoate, and tin versatylate.

[0090] Examples of carboxylic acids include lauric acid, 2-ethylhexanoic acid, neodecanoic acid, and versatic acid. Examples of amine compounds include octylamine, laurylamine, stearylamine, and N,N-diethylamino-1,3-propanediamine. The mixing ratio of carboxylic acids and amine compounds can be any ratio depending on the desired curing rate.

[0091] Examples of alkoxy metals include titanium tetraethoxide, titanium tetraisopropoxide, and titanium tetrabutoxide.

[0092] When the composition contains a reactive functional group-containing glyceride compound having a (meth)acryloyl group as component (A), a radical polymerization initiator can be suitably used as component (C), which is a compound that generates a radical species as an active species capable of initiating monomer polymerization in response to external stimuli such as light (active energy rays) or heat.

[0093] If the composition contains a reactive functional group-containing glyceride compound having a (meth)acryloyl group as component (A), there are no particular restrictions on component (C), and known photoradical polymerization initiators and thermal radical polymerization initiators can be used. Compounds described in International Publication No. WO2013 / 047314 and Japanese Patent Application Publication No. 2013-216782 can also be used.

[0094] Preferably, the following can be used as photoradical polymerization initiators: (a) compounds having a hydroxyl group and a phenyl ketone structure, (b) compounds having a benzophenone structure, and (c) compounds having an acylphosphine oxide structure. Preferably, the following can be used as thermal radical polymerization initiators: (d) azo initiators, (e) peroxides, (f) persulfates, and (g) redox initiators.

[0095] (a) Examples of compounds having a hydroxyl group and a phenyl ketone structure include 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxycyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propane-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, and the like.

[0096] (b) Examples of compounds having a benzophenone structure include benzophenone, 3-methoxybenzophenone, 4-methylbenzophenone, 4,4'-bis(diethylamino)benzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, and 4-chloro-4'-benzylbenzophenone.

[0097] (c) Examples of compounds having an acylphosphine oxide structure include bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide.

[0098] (d) Examples of azo initiators include 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (VAZO 33), 2,2'-azobis(2-amidinopropane) dihydrochloride (VAZO 50), 2,2'-azobis(2,4-dimethylvaleronitrile) (VAZO 52), 2,2'-azobis(isobutyronitrile) (VAZO 64), 2,2'-azobis-2-methylbutyronitrile (VAZO 67), 1,1-azobis(1-cyclohexanecarbonitride) (VAZO 88), 2,2'-azobis(2-cyclopropylpropionitrile), and 2,2'-azobis(methylisobutyrate) (V-601).

[0099] (e) Examples of peroxides include benzoyl peroxide, acetyl peroxide, lauroyl peroxide, decanoyl peroxide, dicumyl peroxide, dicetyl peroxydicarbonate, t-butyl peroxyisopropyl monocarbonate, di(4-t-butylcyclohexyl) peroxydicarbonate, di(2-ethylhexyl) peroxydicarbonate, t-butyl peroxypivalate, and t-butyl peroxy-2-ethylhexanoate.

[0100] (f) Examples of persulfates include potassium persulfate, sodium persulfate, and ammonium persulfate.

[0101] (g) Examples of redox initiators include combinations of the persulfate and a reducing agent (sodium metabisulfite, sodium bisulfite, etc.); systems based on organic peroxides and tertiary amines, for example, systems based on benzoyl peroxide and dimethylaniline; and systems based on organic hydroperoxides and transition metals, for example, systems based on cumene hydroperoxide and cobalt naphthate.

[0102] Among the above, as the radical polymerization initiator (C) component, a photoradical polymerization initiator that generates radical species upon irradiation with active energy rays is preferred because it can improve the curability and storage stability of the composition. This configuration has the advantage of good curability and storage stability of the composition. More specifically, component (C) is preferably one or more selected from the group consisting of benzophenone, 4,4'-bis(diethylamino)benzophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide.

[0103] If the composition can be heated to form a coating film, a thermal radical polymerization initiator that generates radical species upon heat may be used as component (C). Alternatively, a combination of a photoradical polymerization initiator and a thermal radical polymerization initiator may be used as component (C). Furthermore, if light irradiation is difficult, or if heat curing is preferred, component (C) is preferably an azo-based initiator or a peroxide. More specifically, in one embodiment, component (C) preferably contains one or more selected from the group consisting of 2,2'-azobis(methyl isobutyrate), t-butyl peroxypivalate, di(4-t-butylcyclohexyl)peroxydicarbonate, t-butylperoxyisopropyl monocarbonate, dicumyl peroxide, benzoyl peroxide, and mixtures thereof, or is preferably one or more selected from the group.

[0104] When the composition contains a radical polymerization initiator as component (C), the composition may further contain a polymerization inhibitor. When the composition contains a radical polymerization initiator as component (C) and a polymerization inhibitor, the advantage is obtained that unintended curing of the composition is reduced and handling becomes easier. The polymerization inhibitor is not particularly limited, and examples thereof include hydroquinone, hydroquinone monomethyl ether, benzoquinone, and p-tert-butylcatechol.

[0105] When the composition contains a reactive functional group-containing glyceride compound having an epoxy group as component (A), as component (C), various catalysts capable of catalyzing the reaction between known epoxy groups can be preferably used.

[0106] Examples of such catalysts capable of catalyzing the reaction between known epoxy groups include (a) ureas such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea, p-chlorophenyl-N,N-dimethylurea (trade name: Monuron), 3-phenyl-1,1-dimethylurea (trade name: Fenuron), 3,4-dichlorophenyl-N,N-dimethylurea (trade name: Diuron), N-(3-chloro-4-methylphenyl)-N',N'-dimethylurea (trade name: Chlortoluron), 1,1-dimethylphenylurea (trade name: Dyhard); (b) tertiary amines such as benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 2-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol incorporated in a poly(p-vinylphenol) matrix, triethylenediamine, N,N-dimethylpiperazine; (c) amines having 1 to 12 carbon atoms (C1-C 12(c) Imidazoles such as alkyleneimidazole, N-arylimidazole, 2-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, N-butylimidazole, 2-undecylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, and addition products of epoxy resin and imidazole; (d) Lewis acid amine complexes such as boron trifluoride amine complex and boron trichloride amine complex; (e) 6-caprolactam; (f) primary thiol compounds. Component (c) may be one of these alone or two or more in combination. Additionally, a latent curing accelerator containing microencapsulated imidazoles or tertiary amines can be used as component (c). Examples of such latent curing accelerators include commercially available products (for example, Novacure HX-3722, manufactured by Asahi Kasei Corporation) HX-3742, Novacure HX-3088, etc. can also be used. (C) As for component, one of these may be used alone, or two or more may be used in combination.

[0107] If the composition contains component (C), the content of component (C) in the composition is not particularly limited, but it is preferably 0.01 parts by weight or more and 100 parts by weight or less per 100 parts by weight of component (A). Having the content of component (C) within this range has the advantage that the composition has an excellent balance between curing speed and storage stability. Within the above range, the lower limit of the content of component (C) in the composition is preferably 0.1 parts by weight or more, more preferably 0.5 parts by weight or more, and even more preferably 1 part by weight or more, per 100 parts by weight of component (A). Furthermore, the upper limit of the content of component (C) is preferably 50 parts by weight or less, more preferably 20 parts by weight or less, and even more preferably 10 parts by weight or less, per 100 parts by weight of component (A).

[0108] <(D) Component: Adhesion agent> The composition preferably contains an adhesion promoter as component (D). The adhesion promoter as component (D) is a component that can improve the adhesion of the coating film obtained by curing the composition. In other words, the composition has the advantage of being able to further improve the adhesion of the coating film obtained by curing the composition.

[0109] The adhesion promoter (D) is not particularly limited as long as it can improve the adhesion of the composition, and adhesion promoters commonly used in the art can be used, but crosslinkable silyl group-containing compounds are preferred, and silane coupling agents are more preferred.

[0110] Examples of silane coupling agents that can be used as component (D) include alkylalkoxysilanes such as methyltrimethoxysilane, dimethyldimethoxysilane, trimethylmethoxysilane, and n-propyltrimethoxysilane; alkylisopropenoxysilanes such as dimethyldiisopropenoxysilane and methyltriisopropenoxysilane; vinyl-type unsaturated group-containing silanes such as vinyltrimethoxysilane, vinyldimethylmethoxysilane, vinyltriethoxysilane, γ-methacryloyloxypropylmethyldimethoxysilane, and γ-acroyloxypropylmethyltriethoxysilane; silicone varnishes; and polysiloxanes.

[0111] Furthermore, as the silane coupling agent for component (D), a silane coupling agent having both an organic group containing atoms other than carbon and hydrogen atoms, such as an epoxy group, isocyanate group, isocyanurate group, carbamate group, amino group, mercapto group, carboxyl group, halogen group, or (meth)acrylic group, and a crosslinkable silyl group can also be used.

[0112] Examples of such silane coupling agents include epoxysilanes such as γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltriethoxysilane, γ-glycidoxypropylmethyldiisopropenoxysilane, and other epoxysilanes, as well as alkoxysilanes having epoxy groups; γ-isocyanatetopropyltrimethoxysilane, γ-isocyanatetopropyltrimethoxysilane, and other epoxysilanes; and γ-isocyanatetopropyltrimethoxysilane. Alkoxysilanes having an isocyanate group, such as anetopropyltriethoxysilane, γ-isocyanatetopropylmethyldiethoxysilane, and γ-isocyanatetopropylmethyldimethoxysilane; Alkoxysilanes having an isocyanurate group, such as tris(trimethoxysilyl)isocyanurate; γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropylmethyldimethoxysilane, γ-aminopropylmethyldiethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimeth Alkoxysilanes having amino groups such as xysilane, N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldiethoxysilane, γ-ureidopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-benzyl-γ-aminopropyltrimethoxysilane, N-vinylbenzyl-γ-aminopropyltriethoxysilane; γ-mercaptopropyltrimethoxysilane Alkoxysilanes having a mercapto group, such as γ-mercaptopropyltriethoxysilane, γ-mercaptopropylmethyldimethoxysilane, and γ-mercaptopropylmethyldiethoxysilane; Alkoxysilanes having a carboxyl group, such as β-carboxyethyltriethoxysilane, β-carboxyethylphenylbis(2-methoxyethoxy)silane, and N-β-(carboxymethyl)aminoethyl-γ-aminopropyltrimethoxysilane; Alkoxysilanes having a halogen group, such as γ-chloropropyltrimethoxysilane;Examples include alkoxysilanes having a (meth)acryloyl group, such as γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, γ-acryloxypropyltriethoxysilane, γ-acryloxypropyltriethoxysilane, methacryloxymethyltrimethoxysilane, methacryloxymethyltriethoxysilane, acryloxymethyltrimethoxysilane, and acryloxymethyltriethoxysilane; and others.

[0113] Furthermore, derivatives of these silane coupling agents, such as amino-modified silyl polymers, silylated amino polymers, unsaturated aminosilane complexes, phenylamino long-chain alkylsilanes, aminosilylated silicones, and silylated polyesters, can also be used as component (D).

[0114] Among the various silane coupling agents described above, alkoxysilanes having an epoxy group or a (meth)acryloyl group in the molecule are more preferred as component (D) from the viewpoint of curability and adhesion.

[0115] (D) Component may also be an adhesion promoter other than a silane coupling agent (other adhesion promoter). Such other adhesion promoters are not particularly limited, but examples include phenolic resins, tackifiers, sulfur, alkyl titanates, aromatic polyisocyanates, etc.

[0116] (D) Component may be one of the above-mentioned silane coupling agents used alone or in a mixture of two or more, one of the above-mentioned other adhesion promoters used alone or in a mixture of two or more, or a silane coupling agent and other adhesion promoters used in a mixture.

[0117] If the composition contains a silane coupling agent as component (D), it is preferable that the composition further contains a crosslinkable silyl group condensation catalyst. By including both the silane coupling agent (component (D)) and the crosslinkable silyl group condensation catalyst in the composition, the adhesion of the coating film obtained by curing the composition can be further improved. The crosslinkable silyl group condensation catalyst is not particularly limited, and various catalysts capable of catalyzing reactions between hydrolyzable silyl groups, as exemplified as component (C), can be suitably used.

[0118] If the composition contains component (D), the content of component (D) in the composition is not particularly limited, but it is preferably 0.01 parts by weight or more and 100 parts by weight or less per 100 parts by weight of component (A). Having component (D) within this range provides the advantage that the composition has a viscosity that is easy to apply while exhibiting excellent adhesion to the substrate (also called the adherend). Within the above range, the lower limit of the content of component (D) in the composition is preferably 0.1 parts by weight or more, more preferably 0.5 parts by weight or more, and even more preferably 1 part by weight or more, per 100 parts by weight of component (A). Furthermore, the upper limit of the content of component (D) is preferably 50 parts by weight or less, more preferably 20 parts by weight or less, and even more preferably 10 parts by weight or less, per 100 parts by weight of component (A).

[0119] <Other ingredients> This composition may optionally contain components other than those described above (A) and (B), as well as optional components (C) and (D) (hereinafter sometimes referred to as "other components").

[0120] Other such components include fillers, fine hollow particles, plasticizers, preservatives and stabilizers, antioxidants, UV absorbers, flame retardants, antistatic agents, pigments, thixotropic agents (anti-sagging agents), compatibilizers, curing modifiers, radical inhibitors, metal deactivators, ozone degradation inhibitors, phosphorus-based peroxide decomposers, lubricants, defoamers, foaming agents, termite repellents, fungicides, and light stabilizers, as well as elastomers (e.g., styrene-based block copolymers) that adjust the rubber properties of the cured product, thiol compounds, tertiary amine compounds, and solvents.

[0121] Specific examples of other components are described in paragraphs

[0134] to

[0151] of JP 2006-291073, paragraphs

[0232] to

[0235] of JP 2007-308692, paragraphs

[0089] to

[0093] of International Publication WO2005 / 116134, JP 4-69659, JP 7-108928, JP 63-254149, JP 64-22904, JP 2001-72854, and paragraphs

[0111] to

[0143] of International Publication WO2023 / 162664, etc. These other components can be suitably used as other components in the present composition.

[0122] <Method for producing this composition> This composition can be obtained by mixing components (A) and (B) described above with components (C), (D), and / or other components as optional.

[0123] The method for mixing multiple components is not particularly limited and may include using a hand mixer, static mixer, planetary mixer, disper, roll, kneader, single-screw extruder, twin-screw extruder, Banbury mixer, Brabender, high-shear mixer, etc. Mixing may be carried out in the dark as needed.

[0124] This composition may be a one-component type, a two-component type, or a multi-component type with three or more components.

[0125] In the case of a one-component composition, since all components are pre-mixed, it is preferable to either dehydrate and dry any raw materials containing moisture before use, or dehydrate them during the manufacturing of the composition by heating or reducing the pressure, or by adding a component that has a dehydrating effect.

[0126] <Method of applying this composition> The method for applying this composition to a substrate is not particularly limited, and known methods for applying coating agents can be used. Such methods include dispensing using cartridges or automatic dispensing machines, spraying, inkjet printing, screen printing, gravure printing, dipping, spin coating, die coating, and methods using caulking guns and spray guns.

[0127] The substrate to which this composition is applied is not particularly limited and may be either an organic or inorganic substrate, and may be coated. Specifically, examples of substrates to which this composition is applied include metals (e.g., aluminum, stainless steel), glass, porcelain, tiles, stone, wood, resin molded products, mortar, slate, ABS, acrylic, PVC-coated steel sheets, polycarbonate, galvalume steel sheets (registered trademark), electrodeposited coated sheets, cold-rolled steel sheets, calcium silicate boards, synthetic fibers, natural fibers, paper products, and release paper. Furthermore, these substrates may be coated with acrylic paints, acrylic urethane paints, acrylic silicone paints, fluoropolymer paints, etc.

[0128] When applying this composition, if the composition has high viscosity at room temperature and is difficult to handle, it may be applied after being heated to the desired viscosity. The temperature of the composition after heating is preferably 100°C or lower, and more preferably 80°C or lower. Heating the composition to 100°C or lower has the advantage that component (C) is less likely to volatilize. Therefore, safety advantages and the advantage of preventing changes in the mixing ratio of each component in the composition are obtained.

[0129] [3. Coating film] In one embodiment of the present invention, a coating film is provided obtained by curing the coating composition described in section [2. Coating Composition] (i.e., the present composition). The coating film according to one embodiment of the present invention is also simply referred to as the present coating film.

[0130] This coating film, using this composition as a raw material, is an environmentally friendly coating film that utilizes non-fluorine compounds while exhibiting excellent adhesion to the substrate, water repellency, and durability. The adhesion, water repellency, and durability of this coating film are evaluated by the method described in the examples.

[0131] <Method for manufacturing coating film> In providing this coating film, the curing method of the composition (which can also be called the manufacturing method of the coating film) is not particularly limited, but for example, the coating film can be obtained by drying the composition. That is, in one embodiment of the present invention, a manufacturing method of the coating film is provided, which includes a step of drying the composition.

[0132] In the method for manufacturing this coating film, the temperature at which the coating film is dried may be room temperature or it may be heated to about 50°C. Generally, curing tends to proceed faster at higher temperatures than at lower temperatures, so it is preferable to heat the coating film when drying it. [Examples]

[0133] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Measurements and evaluations in the examples and comparative examples were performed by the following methods.

[0134] [Measurement method and evaluation method] < 1 H NMR analysis> Compounds obtained in each synthesis example 1 1H NMR analysis was performed under the following conditions: Equipment: Bruker Avance III 400MHz.

[0135] <Measuring the water contact angle> For each example and comparative example, a sample was prepared and a coating film was formed on the substrate. Using a CA-X contact angle meter manufactured by Kyowa Interface Science Co., Ltd., pure water was dropped onto the coating film surface under conditions of 25°C and 50% humidity to determine the contact angle θ.

[0136] <Water droplet drop test> For each example and comparative example, a single drop of water was applied to the surface of the sample, which had a coating film formed on the substrate, using a dropper. Next, the substrate was tilted at a 45-degree angle, and the way the water droplet fell was evaluated. The evaluation was performed on a 5-point scale, as follows: A rating of 5 indicated the best water repellency, and a rating of 1 indicated the worst water repellency. Rating 5: The water droplets fell off immediately. Rating 4: The water droplets fell slowly. Rating 3: Most of the water droplets fell off, but some remained. Rating 2: The water droplets fell in a way that made them spread out. Rating 1: No water droplets fell.

[0137] <Wipe resistance test> The surface of each sample, prepared in each example and comparative example, with a coating film formed on the substrate, was rubbed with a finger and visually evaluated in the following two stages. +(Excellent): When the surface of the paint film was wiped, no wipe marks were left behind. -(Defective): When the surface of the coating was wiped, wipe marks remained.

[0138] <Durability evaluation> • Evaluation of heat resistance Samples with coatings formed on substrates prepared in each example and comparative example were cured in a 100°C oven for 1 hour, and then cooled by standing at room temperature (heat resistance test). After the heat resistance test, the samples were subjected to water contact angle measurement, water droplet drop test, and wipe resistance test, and their heat resistance was evaluated according to the following criteria. +(Excellent): The change in water contact angle before and after the heat resistance test was within 10°C, and there was no decrease in the evaluation of either the water droplet test or the wipe resistance test. -(Defective): The change in water contact angle is 10°C or more before and after the heat resistance test, or the evaluation in either the water droplet test or the wipe resistance test deteriorated.

[0139] • Evaluation of water resistance Samples with coatings formed on substrates prepared in each example and comparative example were immersed in pure water at room temperature for 3 days, then removed and allowed to dry at room temperature for 1 day (water resistance test). After the water resistance test, the samples were subjected to water contact angle measurement, water droplet drop test, and wipe resistance test, and their water resistance was evaluated according to the following criteria. +(Excellent): The change in water contact angle before and after the water resistance test was within 10°C, and there was no decrease in the evaluation of either the water droplet test or the wipe resistance test. -(Defective): The change in water contact angle before and after the water resistance test was 10°C or more, or the evaluation in either the water droplet test or the wipe resistance test deteriorated.

[0140] • Evaluation of chemical resistance Samples with coatings formed on substrates prepared in each example and comparative example were immersed in ethanol at room temperature for 3 days, then removed and allowed to dry at room temperature for 1 day (chemical resistance test). After the chemical resistance test, the samples were subjected to water contact angle measurement, water droplet drop test, and wipe resistance test, and their water resistance was evaluated according to the following criteria. +(Excellent): The change in water contact angle before and after the chemical resistance test was within 10°C, and there was no decrease in the evaluation of either the water droplet test or the wipe resistance test. -(Defective): The change in water contact angle is 10°C or more before and after the chemical resistance test, or the evaluation in either the water droplet test or the wipe resistance test deteriorated.

[0141] • Durability evaluation Based on the above evaluations of heat resistance, water resistance, and chemical resistance, durability was evaluated according to the following criteria. + (Excellent): Excellent in all aspects of heat resistance, water resistance, and chemical resistance (all receive a + rating). -(Defective): The product has a poor evaluation in one of the following areas: heat resistance, water resistance, or chemical resistance (some products have a negative evaluation).

[0142] 〔material〕 The materials used in the following examples and comparative examples are as follows:

[0143] <(A) component> • Hydrolyzable silyl group-containing glycerides (GS-1): A mixture of compounds of formula (1) and formula (2) (where R is present in formulas (1) and (2)). 1 and R 2 (where is a -(CO)(NH)CH2CH2CH2- group, X is -Si(OMe)3, and FA is oleic acid.) • Hydrolyzable silyl group-containing glycerides (GS-2): A mixture of compounds of formula (3) and formula (4) (wherein R is present in formulas (3) and (4)). 3 and R 4 (where is a -(CO)(NH)CH2CH2CH2- group, X is -Si(OMe)3, and FA is oleic acid.) • Hydrolyzable silyl group-containing glycerides (GS-3): A mixture of compounds of formula (3) and formula (4) (where R is present in formulas (3) and (4)). 3 and R 4 (where is a -(CO)(NH)CH2CH2CH2- group, X is -Si(OMe)3, and FA is stearic acid.) • Hydrolyzable silyl group-containing glycerides (GS-4): A mixture of compounds of formula (1) and formula (2) (where R is present in formulas (1) and (2)). 1 and R 2 (where is a -(CO)(NH)CH2CH2CH2- group, X is -Si(OMe)3, and FA is stearic acid.) • Methacrylic group-containing glyceride (GM-1): A mixture of formula (1) and formula (2) (where R is present in formulas (1) and (2)). 1 and R 2 (where is a single bond, X is a methacrylic group, and the main components of FA are palmitic acid and stearic acid.) • Methacrylated triglycerides and trimethylolpropane ester mixtures (GM-2, GM-3, GM-4): The main components are compounds of formulas (1) to (4) and (14) to (17), as well as oils and fats in which three fatty acids are bonded. Here, in formulas (1) to (4) and (14) to (17), R 1 From R 6 and R 9 From R 14 All of them are single bonds, and the main components of FA are palmitic acid and stearic acid. • Acryloyl group-containing triglycerides (GM-5, GM-6): Mixtures of compounds of formula (1) and formula (2) (where R is present in formulas (1) and (2)). 1 and R 2 (where is a single bond, X is an acryloyl group, and the main components of FA are palmitic acid and stearic acid).

[0144] <(A') component (comparative component of (A) component)> Glycerol dioleate Glycerol oleate <(B) component> • Cyclopentane Hexane <(C) component> • U-220H (manufactured by Nitto Chemical Co., Ltd., dibutyltin-based catalyst, "Neostan U-220H") • 2-hydroxy-2-methyl-1-phenylpropan-1-one (IGM Resins, "Omnirad1173") • Bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (IGM Resins, "Omnirad819") <(D) component> • N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (manufactured by Momentive Performance Materials, "SILQUEST A-1120 SILANE") • 2-Methacryloyloxyethyl acid phosphate (Kyoeisha Chemical Co., Ltd. "Light Ester P-1M") • 3-Methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Silicone Co., Ltd., "KBM-503") <Comparative coating agent composition> • Comparative composition-1: FK Superhydrophobic Spray (manufactured by FK Corporation, containing silicone resin and fluororesin as water-repellent components) • Comparative composition-2: Ultra-strong multi-purpose waterproof spray (manufactured by Henkel Japan, containing a fluororesin as a water-repellent component).

[0145] [Synthesis Example (Synthesis of Component (A))] <Synthesis Example 1> Glycerol dioleate (10.0 g) was stirred under high vacuum at 100°C for 1 hour. Next, the system was purged with nitrogen, and (3-isocyanatepropyl)trimethoxysilane (3.1 g) and U-830 (urethane curing catalyst, manufactured by Nitto Kasei, "Neostan U-830") (0.50 μL) were added. Stirring at 100°C for 4 hours yielded a pale yellow liquid hydrolyzable silyl group-containing glyceride (GS-1).

[0146] The obtained hydrolyzable silyl group-containing glyceride (GS-1) 1 The results of the H-NMR were as follows: 1 H NMR (400MHz, CDCl3): δ=5.50-4.85(m, 5H), 4.42-4.06(m, 4H), 3.70-3.49(s, 9H), 3.26-3.06(m, 2H), 2.41-2.21(m, 4 H), 2.15-1.90(m, 8H), 1.71-1.51(m, 6H), 1.48-1.05(m, 40H), 0.90(t, 6H), 0.74-0.54(m, 2H).

[0147] <Synthesis Example 2> Glycerol oleate (10.0 g) was stirred under high vacuum at 110°C for 1 hour. Next, the system was purged with nitrogen, and (3-isocyanatetopropyl)trimethoxysilane (10.9 g) and U-830 (0.5 μL) were added. Stirring at 110°C for 3 hours yielded a pale yellow liquid hydrolyzable silyl group-containing glyceride (GS-2).

[0148] The obtained hydrolyzable silyl group-containing glyceride (GS-2) 1 The results of the H-NMR were as follows: 1 H NMR (400MHz, CDCl3): δ=5.46-4.74(m, 3H), 4.40-4.00(m, 4H), 3.57(s, 18H), 3.26-2.88(m, 4H), 2.41-2.21(m, 2H), 2.15-1.87(m, 4H), 1.75-1.48(m, 6H), 1.48-1.05(m, 20H), 0.88(t, 3H), 0.64(t, 4H).

[0149] <Synthesis Example 3> Glycerol stearate (20.0 g) was stirred under high vacuum at 110°C for 1 hour. Next, the system was purged with nitrogen, and (3-isocyanatepropyl)trimethoxysilane (21.8 g) and U-830 (1.0 μL) were added. By stirring at 110°C for 2 hours, a white, waxy, hydrolyzable silyl group-containing glyceride (GS-3) was obtained.

[0150] The obtained hydrolyzable silyl group-containing glyceride (GS-3) 1 The results of the H-NMR were as follows: 1 H NMR (400MHz, CDCl3): δ=5.28-4.76(m, 1H), 4.40-4.00(m, 4H), 3.57(s, 18H), 3.26-2.90(m, 4H), 2.43 -2.21(m, 2H), 1.75-1.48(m, 6H), 1.48-1.05(m, 28H), 0.88(t, 3H), 0.64(t, 4H).

[0151] <Synthesis Example 4> Glycerol distearate (20.0 g) was stirred under high vacuum at 100°C for 1 hour. Next, the system was purged with nitrogen, and (3-isocyanatepropyl)trimethoxysilane (6.2 g) and U-830 (1.0 μL) were added. By stirring at 100°C for 3 hours, a white, waxy, hydrolyzable silyl group-containing glyceride (GS-4) was obtained.

[0152] The obtained hydrolyzable silyl group-containing glyceride (GS-4) 1 The results of the H-NMR were as follows: 1 H NMR (400MHz, CDCl3): δ=5.38-4.83(m, 1H), 4.40-4.04(m, 4H), 3.57(s, 9H), 3.26-3.01(m, 2H), 2.42- 2.20(m, 4H), 1.75-1.50(m, 6H), 1.44-1.05(m, 56H), 0.88(t, 6H), 0.64(t, 2H).

[0153] <Synthesis Example 5> 552 g of super-hardened palm oil (manufactured by Kaneka Corporation) and 194 g of ethylhexyl methacrylate (reagent) were mixed and heated to 90°C under reduced pressure. 2.2 g of sodium methoxide (reagent) was added and the mixture was stirred at 90°C under reduced pressure for 1 hour to allow the reaction to proceed. 2.1 L of hexane was added to the resulting reaction product and heated to dissolve it. The mixture was incubated at 10°C for 24 hours, and the precipitated crystals were removed by filtration. The filtrate was incubated at -20°C for 24 hours, the precipitated crystals were filtered, and the resulting crystals were washed with 500 ml of hexane incubated at -20°C. The hexane was dried under reduced pressure to obtain methacrylate-containing glyceride (GM-1). The melting point of the reaction product was 31°C.

[0154] The obtained methacrylate-containing glyceride (GM-1) 1 The results of the H-NMR were as follows: 1 H NMR: (400MHz, CDCl3): δ=6.11(m, 1H), 5.61(m, 1H), 5.33(m, 1H), 4.44-4.11(m, 4.6H), 3.80-3.69(m, 0.1 1H), 3.69-3.63(s, 0.041H), 2.40-2.24(m, 4.5H), 2.00-1.93(m, 3H), 1.76-1.51(m, 6.7H), 1.50-1.05(br s, 62.2H), 0.97-0.81(t, 7.1H).

[0155] The obtained methacrylate-containing glyceride (GM-1) was subjected to gas chromatography analysis. Gas chromatograph: Agilent GC7890B, detector: FID, column: Agilent DB-1 1m × 0.25mm × 0.25μm, inlet temperature: 340°C, detector temperature: 350°C, oven temperature: increased from an initial temperature of 100°C to 320°C at a heating rate of 20°C / min, held at 320°C for 5 minutes, and measurement was performed with a total runtime of 16 minutes.

[0156] The gas chromatography results of the obtained methacrylic group-containing glycerides (GM-1) were as follows: out of 100% by weight of methacrylated triglycerides, (a) 26.6% by weight of triglycerides having 2 stearic acid groups and 1 methacrylic acid group per molecule, (b) 41.5% by weight of triglycerides having 1 stearic acid group, 1 palmitic acid group, and 1 methacrylic acid group, and (c) palmitic acid group per molecule (d) a triglyceride having two stearic acid molecules and one methacrylic acid molecule, 18.2% by weight; (e) a triglyceride having two stearic acid molecules and two methacrylic acid molecules (dimethacrylic); (f) a triglyceride having two palmitic acid molecules and two methacrylic acid molecules (dimethacrylic); and 21.54% by weight of residues such as tri fatty acids and / or fatty acid ethylhexyl derived from the raw materials.

[0157] <Synthesis Example 6> 567 g of super-hardened palm oil (manufactured by Kaneka Corporation) and 113 g of trimethylolpropane trimethacrylate (reagent) were mixed and heated to 90°C under reduced pressure. 2.2 g of sodium methoxide (reagent) was added and the mixture was stirred at 90°C under reduced pressure for 1 hour to allow the reaction to proceed. The resulting reaction product was washed with water and dried under reduced pressure to obtain a mixture of methacrylated triglyceride and trimethylolpropane ester (GM-2).

[0158] Gas chromatography analysis was performed in the same manner as in Synthesis Example 5. The gas chromatography results of the obtained methacrylate triglyceride and trimethylolpropane ester mixture (GM-2) were as follows: In 100% by weight of the methacrylate triglyceride and trimethylolpropane ester mixture (GM-2), (a) 3.93% by weight of triglycerides having one palmitic acid molecule and two methacrylic acid molecules per molecule, (b) triglycerides having one stearic acid molecule and two methacrylic acid molecules, and trimethylolpropane esters having one palmitic acid molecule and two methacrylic acid molecules. (c) Trimethylolpropane ester having one stearic acid molecule and two methacrylic acid molecules, totaling 6.61% by weight, (d) Triglyceride having two palmitic acid molecules and one methacrylic acid molecule, totaling 7.19% by weight, (e) Triglyceride having one palmitic acid molecule, one stearic acid molecule and one methacrylic acid molecule, and trimethylolpropane ester having two palmitic acid molecules and one methacrylic acid molecule, all appear as peaks at the same location, totaling 16.65% by weight, (f) Triglycerides containing two stearic acid molecules and one methacrylic acid molecule, as well as trimethylolpropane esters containing one palmitic acid molecule, one stearic acid molecule, and one methacrylic acid molecule, appeared as peaks at the same location, totaling 14.09% by weight, (g) trimethylolpropane esters containing two stearic acid molecules and one methacrylic acid molecule at 4.41% by weight, (h) triglycerides containing three palmitic acid molecules at 2.44% by weight, (i) triglycerides containing two palmitic acid molecules and one stearic acid molecule, and palmitic acid (j) Trimethylolpropane esters with three molecules appear as peaks at the same location, totaling 7.98% by weight; (k) Triglycerides with one palmitic acid molecule and two stearic acid molecules, and trimethylolpropane esters with two palmitic acid molecules and one stearic acid molecule, appear as peaks at the same location, totaling 11.41% by weight; (k) Triglycerides with three stearic acid molecules, and trimethylolpropane esters with two stearic acid molecules and one palmitic acid molecule, appear as peaks at the same location, totaling 7%.It contained 52% by weight of (l) trimethylolpropane ester having three stearic acid groups, 1.99% by weight of (m) residues derived from raw materials such as trimethylolpropane trimethacrylate, glycerides, or trimethylolpropane esters.

[0159] [Examples and Comparative Examples] <Examples 1 to 6, Comparative Examples 1 and 2> (Manufacturing of coating agent compositions) A coating agent composition was obtained by weighing each component according to the types and proportions listed in Table 1 and mixing them uniformly.

[0160] (Formation of coating film and evaluation of each physical property) The tin-coated surface of the float glass substrate was degreased using acetone, and then the coating composition prepared above was spray-applied. The coating composition was cured by drying in a 50°C oven for 30 minutes, and samples were prepared in which a coating film formed by the cured coating composition was formed on the substrate. Various physical properties were evaluated using each of the obtained samples. The results are shown in Table 1.

[0161] <Comparative Examples 3 and 4> (Manufacturing of coating agent compositions) The commercially available coating agent compositions described above as comparative coating agent compositions were used as is.

[0162] (Formation of coating film and evaluation of each physical property) Samples were prepared by applying the comparative coating agent composition to the same substrate as described above, according to the usage instructions provided for each product, and drying at room temperature for 30 minutes, thereby forming a coating film on the substrate after the comparative coating agent composition had hardened. Various physical properties were evaluated using each of the obtained samples. The results are shown in Table 1.

[0163] [Table 1]

[0164] <Result-1> The results from Examples 1 to 6 show that this composition can provide a coating film with excellent adhesion to the substrate and water repellency, and that the resulting coating film also exhibits excellent durability. Furthermore, a comparison of Examples 1 to 6 with Comparative Examples 1 and 2 shows that in order to provide a coating film with excellent adhesion to the substrate, water repellency, and durability as described above, it is necessary to use a glyceride compound containing a reactive functional group having a specific structure. Moreover, a comparison of Examples 1 to 6 with Comparative Examples 3 and 4 shows that this composition, while being an environmentally friendly coating agent composition using a non-fluorine-based compound, has water repellency comparable to conventional coating agent compositions using fluorine-based compounds, and furthermore, exhibits superior adhesion to equipment and excellent durability.

[0165] <Example 7> Using the coating composition of Example 3, samples were prepared by forming a coating film in the same manner as in Example 3, except that the substrate was changed to one of the adherends shown in Table 2 below. The water contact angle of each adherend before application of the coating composition, and of each prepared sample, was measured to evaluate the water-repellent effect on each substrate. The results are shown in Table 2.

[0166] In Table 2, "PMMA" represents poly(methyl methacrylate), "FRP" represents fiber-reinforced plastic, "PVC" represents poly(vinyl chloride), "PBT" represents poly(butylene terephthalate), and "PC" represents polycarbonate.

[0167] [Table 2]

[0168] <Result-2> As shown in the results of Example 7 in Table 2, each sample coated with this composition showed an increased water contact angle compared to before the coating was formed. This indicates that this composition can impart water repellency to substrates other than glass.

[0169] <Examples 8 to 10> (Manufacturing of coating agent compositions) A coating agent composition was obtained by weighing each component according to the types and proportions listed in Table 3 and mixing them uniformly.

[0170] (Formation of coating film and evaluation of each physical property) The tin-coated surface of the float glass substrate was degreased using acetone, and then the coating agent composition prepared above was spray-applied. The UV irradiation device (Fusion UV Systems Japan, Model: LH6) was then used to irradiate the surface with UV light (irradiation conditions: illuminance 500 mW / cm²). 2 , light intensity 5,000mJ / cm 2 The coating agent composition was cured, and samples were prepared in which a coating film formed by the cured coating agent composition was formed on the substrate. Various physical properties were evaluated using each of the obtained samples. The results are shown in Table 3.

[0171] [Table 3]

[0172] <Result-3> The results from Examples 8 to 10 show that even when a (meth)acryloyl group-containing glyceride compound is used as component (A), it is possible to provide a coating film with excellent adhesion to the substrate and water repellency.

[0173] <Example 11> Samples were prepared by forming a coating film in the same manner as in Example 8, except that a coating agent composition prepared in the same manner as in Example 8 was used, except that the substrate was changed to one of the adherends shown in Table 4 below. The water contact angle of each adherend before application of the coating agent composition and each prepared sample was measured to evaluate the water-repellent effect on each substrate. The results are shown in Table 4.

[0174] In Table 4, the filter paper used was Advantec Toyo Co., Ltd.'s Qualitative Filter Paper No. 2, 90mm, and the hair fiber used was Kaneka Corporation's "Kanekalon AFS".

[0175] [Table 4]

[0176] <Result-4> As shown in the results of Example 11 in Table 4, each sample with a coating film formed from this composition was able to impart water repellency to paper or fibers that did not have water repellency. Here, "unmeasurable" indicates that the water droplet soaked into the substrate the moment it was dropped, did not form a droplet, and therefore it was difficult to measure the contact angle.

[0177] Thus, by using a coating film obtained by curing this composition, hydrophobic and water-repellent properties can be imparted to the surface of various substrates.

[0178] In particular, by imparting hydrophobicity and water repellency to paper or fibers, each substrate repels water, preventing water from seeping in. Therefore, it can be used as an alternative material to resin-based coatings and modifiers that were conventionally used to impart water resistance. Furthermore, in Table 4, both GM-1 and GM-2 coated filter papers could be written on without any problems using pencils and ballpoint pens.

[0179] <Example 12> For the filter paper coated in Example 11, a 5cm square piece of masking tape was attached to the filter paper, and a 1kg weight was applied for 10 minutes. After that, the tape was removed, and the amount of fiber from the filter paper that remained attached was observed to test the peelability. The evaluation was performed according to the following criteria. 5 points: Almost no filter paper fibers adhere to the tape, and the peelability is extremely good. 4 points: Less than 10% of the tape surface area is covered with filter paper fibers, but the peelability is good. 3 points: Although more than 10% to 20% of the tape surface area is covered by filter paper fibers, the peelability is within acceptable limits. Two points: More than 20% but less than 50% of the tape surface area is covered by filter paper fibers, resulting in poor peelability. 1. Filter paper fibers are attached to more than 50% of the tape surface area, resulting in extremely poor peelability.

[0180] [Table 5]

[0181] <Result-5> As shown in the results of Example 12 in Table 5, each sample with a coating film formed from this composition exhibited good tape peelability, meaning that it was possible to impart peelability to the surface of the adherend.

[0182] Next, the UV irradiation curing treatment of (meth)acryloyl group-containing glycerides used in the coating film formation of Examples 8 to 9 was evaluated in place of the heating curing treatment.

[0183] <Synthesis Example 7> Synthesis of GM-3, a mixture of methacrylated triglycerides and trimethylolpropane esters Except for using high-oleic sunflower oil (manufactured by Showa Sangyo Co., Ltd., olein-rich) instead of super-hardened palm oil and changing the amount of trimethylolpropane trimethacrylate (reagent) to 225 g, the same procedure as in Synthesis Example 6 was used to obtain GM-3, a mixture of methacrylated triglycerides and trimethylolpropane ester.

[0184] <Synthesis Example 8> Synthesis of GM-4, a mixture of methacrylated triglycerides and trimethylolpropane esters A mixture of methacrylated triglycerides and trimethylolpropane esters, GM-4, was obtained in the same manner as in Synthesis Example 7, except that soybean oil (manufactured by Kaneka Corporation) was used instead of high-oleic sunflower oil.

[0185] <Synthesis Example 9> Synthesis of Acryloyl Group-Containing Glyceride GM-5 400 g of tung oil (reagent) and 116 g of glycerol triacrylate (Aronix 930 manufactured by Toagosei Co., Ltd.) were mixed and heated to 50°C under reduced pressure. 30 g of lipase (Lipozyme TL-IM manufactured by Novozymes Japan) was added, and the mixture was reacted for 72 hours with stirring. The obtained reaction product was filtered to remove the lipase, and glyceride GM-5 containing an acryloyl group was obtained.

[0186] <Synthesis Example 10> Synthesis of glyceride GM-6 containing an acryloyl group Glyceride GM-6 containing an acryloyl group was obtained in the same manner as in Synthesis Example 9, except that linseed oil (reagent) was used instead of tung oil.

[0187] <Examples 13 to 17> Component (A), component (B), and component (C) were mixed at the ratios shown in Table 6 to obtain a coating agent composition.

[0188] Next, each of the obtained coating agent compositions was spray-coated onto filter paper (Qualitative Filter Paper No. 2 manufactured by Advantec Toyo Co., Ltd.) and dried at 170°C for 20 minutes.

[0189] Thereafter, the water contact angle was measured in the same manner as in Example 1.

[0190] Also, the peelability of the tape was evaluated in the same manner as in Example 12. The peelability of the tape was evaluated for two conditions, namely, after standing at room temperature for 20 minutes and after curing at 60°C for 24 hours, respectively, after tape application.

[0191] The evaluation of the peelability after standing at room temperature for 20 minutes was performed according to the following criteria. 5 points: Almost no fibers of the filter paper adhered to the tape, and the peelability was extremely good. 4 points: Fibers of the filter paper adhered to 10% or less of the tape area, and the peelability was good. 3 points: Fibers of the filter paper adhered to more than 10% and 20% or less of the tape area, and the peelability was within the acceptable range. 2 points: Fibers of the filter paper adhered to more than 20% and 50% or less of the tape area, and the peelability was poor. 1 point: More than 50% of the filter paper fibers are attached to the tape surface, and the peelability is extremely poor.

[0192] Regarding the evaluation of peelability after curing at 60°C for 24 hours, the following criteria were used. 5 points: Almost no filter paper fibers are attached to the tape, and the peelability is extremely good. 4 points: 20% or less of the filter paper fibers are attached to the tape surface, and the peelability is good. 3 points: More than 20% and 40% or less of the filter paper fibers are attached to the tape surface, and the peelability is within the acceptable range. 2 points: More than 40% and 60% or less of the filter paper fibers are attached to the tape surface, and the peelability is poor. 1 point: More than 60% of the filter paper fibers are attached to the tape surface, and the peelability is extremely poor.

[0193] [[ID=ID=18]]Furthermore, the writing property of the coating film formed by curing each coating agent composition was evaluated. This evaluation was carried out by writing characters on the coating film surface with an oil-based magic pen, an oil-based ballpoint pen, and a pencil (all commercially available), and visually evaluating them in the following three levels. 3 points: There is no bleeding or repelling, and the written characters can be distinguished. 2 points: There is bleeding or repelling, but the written characters can be distinguished. 1 point: There is significant bleeding or repelling, and the written characters cannot be distinguished.

[0194] The above evaluation results were summarized in Table 6. [[ID=ID=30]]

[0195] [[ID=ID=31]] [[ID=ID=32]]<Examples 18 to 22> A coating agent composition was prepared and its physical properties were evaluated in the same manner as in Examples 13 to 17 except that the (C) component was not included. The evaluation results are shown in Table 6.

[0196] <Comparative Example 5> Each test was carried out in the same manner as in Examples 13 to ID=17 except that the filter paper was used as it was without applying the coating with this composition, and the physical properties were evaluated. The evaluation results are shown in Table 6.

[0197]

Table 6

[0198] <Result-6> A comparison of Example 13 and Example 18 in Table 6 shows that when GM-1 is used as component (A), the coating film obtained by curing the composition with the curing catalyst (component (C)) exhibits superior water contact angle and tape peelability, meaning that a coating film with superior water repellency and peelability can be provided. Furthermore, since text can be inscribed on the coated surface, it can be seen that various types of printing can be performed on the coating film obtained by curing the coating agent composition of the present invention.

[0199] Similarly, by comparing Example 14 with Example 19, Example 15 with Example 20, Example 16 with Example 21, and Example 17 with Example 22, it can be seen that the coating film obtained by curing the composition with the curing catalyst component (C) has superior water contact angle and tape peelability, and is superior in water repellency and peelability. Furthermore, by comparing Examples 18 to 22 with Comparative Example 5, it can be seen that the coating film containing the coating agent component (A) has superior peelability compared to the case of the substrate alone.

[0200] From these results, it can be seen that this composition provides a non-fluorine-based coating agent that exhibits excellent water repellency even when heated and cured. [Industrial applicability]

[0201] This composition can be suitably used as a coating agent composition to impart water repellency to various substrates such as metals (e.g., aluminum, stainless steel), glass, porcelain, tiles, stone, wood, resin molded products, mortar, slate, ABS, acrylic, PVC-coated steel sheets, polycarbonate, galvalume steel sheets (registered trademark), electrodeposited coated sheets, cold-rolled steel sheets, calcium silicate boards, synthetic fibers, natural fibers, paper packaging products, and release paper. Furthermore, this composition can also impart peelability, writability, and other properties to the above-mentioned substrates.

Claims

1. (A) Component, which is a glyceride compound containing one or more reactive functional groups represented by the following general formulas (1) to (4) and (14) to (17), (B) Contains a diluent, A coating agent composition in which the content of component (B) is 1 part by weight or more and 100,000 parts by weight or less per 100 parts by weight of component (A): 【Chemistry 1】 (In the above formulas (1) to (4) and (14) to (17), R １ From R ６ and R ９ From R １４ Each of these independently represents a single bond or a divalent organic group, R １５ From R １８ Each of these independently represents an alkyl group having 1 to 5 carbon atoms, and R １９ From R ３０ Each of these independently represents an alkylene group having 1 to 5 carbon atoms, X represents one selected from the group consisting of hydrolyzable silyl groups, (meth)acryloyl groups, and epoxy groups, and FA represents a fatty acid.

2. Furthermore, it contains a curing catalyst, which is component (C). The coating agent composition according to claim 1, wherein the content of component (C) relative to 100 parts by weight of component (A) is 0.01 parts by weight or more and 100 parts by weight or less.

3. Furthermore, it contains component (D), an adhesion promoter, The coating agent composition according to claim 1, wherein the content of component (D) relative to 100 parts by weight of component (A) is 0.01 parts by weight or more and 100 parts by weight or less.

4. A coating film obtained by curing the coating agent composition according to any one of claims 1 to 3.

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