Composition, coating film, and coated article

The inclusion of a cardanol-based compound in compositions with polyaspartic acid ester and polyisocyanate compounds improves dry curing properties, ensuring fast curing rates and a balanced usable life.

JP2025163489APending Publication Date: 2025-10-29CHUGOKU MARINE PAINTS
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Patent Information

Application Number
JP2024066790
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-04-17
Publication Date
2025-10-29

AI Technical Summary

Technical Problem

Compositions containing polyaspartic acid ester and polyisocyanate compounds exhibit insufficient dry curing properties.

Method used

A composition comprising a polyaspartic acid ester, a cardanol-based compound, and a polyisocyanate compound, or a combination of polyaspartic acid ester, polyisocyanate compound, and cardanol-based compound, which enhances the drying and curing properties.

Benefits of technology

The composition achieves excellent dry-curing properties with a fast curing rate, even at low to room temperatures, and maintains a balance between curing speed and usable life.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

To enhance drying and curing properties of a composition comprising a polyaspartic acid ester and a polyisocyanate compound.SOLUTION: This composition includes a first agent containing a polyaspartic acid ester and a cardanol-based compound, and a second agent containing a polyisocyanate compound, or includes a first agent containing a polyaspartic acid ester, a second agent containing a polyisocyanate compound, and a third agent containing a cardanol-based compound.SELECTED DRAWING: None
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Description

[Technical Field]

[0001] The present disclosure relates to, for example, compositions, coatings, and coated articles. [Background technology]

[0002] The polyurea coating film is formed from a coating composition containing a polyamine compound and a polyisocyanate compound. For example, Patent Document 1 discloses a coating composition containing a polyaspartic acid ester and a polyisocyanate compound. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2018 / 163953 Summary of the Invention [Problem to be solved by the invention]

[0004] According to the investigations of the present inventors, it has been found that a composition containing a polyaspartic acid ester and a polyisocyanate compound may have insufficient dry curing properties. An object of the present disclosure is to improve the dry curing properties of a composition containing a polyaspartic acid ester and a polyisocyanate compound. [Means for solving the problem]

[0005] One embodiment of the composition of the present disclosure has a first part containing a polyaspartic acid ester and a cardanol-based compound, and a second part containing a polyisocyanate compound, or has a first part containing a polyaspartic acid ester, a second part containing a polyisocyanate compound, and a third part containing a cardanol-based compound. [Effects of the Invention]

[0006] The composition of the present disclosure has excellent dry-curing properties.

Mode for Carrying Out the Invention

[0007] Each component described in this specification can be used alone or in combination of two or more. In this specification, the term "polymer" may be used without particularly distinguishing between homopolymers and copolymers. That is, the term "polymer" is used in a sense that it may be a homopolymer or a copolymer.

[0008] In this specification, the numerical range n1 to n2 means a numerical range of n1 or more and n2 or less when n1 < n2, and a numerical range of n2 or more and n1 or less when n1 > n2. In this specification, when a lower limit value and an upper limit value are described for a certain element, a numerical range formed by combining a value arbitrarily selected from the described lower limit values and a value arbitrarily selected from the described upper limit values is also regarded as described.

[0009] [Composition] One aspect of the composition of the present disclosure is a first agent containing a polyaspartic acid ester and a cardanol-based compound, [[ID=V20]] a second agent containing a polyisocyanate compound, and has. One aspect of the composition of the present disclosure is a first agent containing a polyaspartic acid ester, a second agent containing a polyisocyanate compound, a third agent containing a cardanol-based compound, and has. One aspect of the composition of the present disclosure contains a polyaspartic acid ester, a cardanol-based compound, and a polyisocyanate compound. In one embodiment, the composition of the present disclosure is a paint composition.

[0010] In this specification, the term "composition" may refer to a multi-component composition in which each component is preserved or stored in a separate container, a mixture containing each component, or a mixture obtained by mixing each component, i.e., a mixture of each component. For example, when specifically describing a mixture obtained by mixing the first and second components of a paint composition, it may also be called a "paint." In this specification, when referring to the content ratio of each component, the mass of the composition means, in the case of a multi-component composition, the total mass of each component (used for mixing) that constitutes the composition, such as the first component and the second component, and the mass of the solid content of the composition means, in the case of a multi-component composition, the total mass of the solid content of each component (used for mixing), such as the solid content of the first component and the solid content of the second component.

[0011] <First and third agents> The first agent, which constitutes one embodiment of the composition of the present disclosure, contains a polyaspartic acid ester, or a polyaspartic acid ester and a cardanol-based compound. The first agent may further contain a polyol compound. The first agent may further contain components other than the polyaspartic acid ester, the cardanol-based compound, and the polyol compound (hereinafter also referred to as "other components"). The third agent, which constitutes one embodiment of the composition of the present disclosure, contains a cardanol-based compound. The third agent may further contain a polyol compound. The third agent may further contain other components.

[0012] <Polyaspartic acid ester> The compositions of the present disclosure contain polyaspartic acid esters. The first agent contains a polyaspartic acid ester. In this specification, the term "polyaspartic acid ester" refers to a compound having two or more aspartic acid ester structures. The term "aspartic acid ester structure" refers to a structure represented by formula (1). The number of aspartic acid ester structures in the polyaspartic acid ester is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2.

[0013] [ka]

[0014] R in formula (1) 1 and R 2 R is independently a monovalent organic group. 1 and R 2 The monovalent organic group in is preferably an organic group that is inactive to an isocyanate group under the drying conditions (curing reaction conditions) described below. Such an inactive organic group is preferably an organic group that does not have an active hydrogen-containing group such as a hydroxy group, an amino group, or a thiol group.

[0015] R 1 and R 2 The monovalent organic group in the formula (I) is preferably a monovalent hydrocarbon group. The number of carbon atoms in the monovalent hydrocarbon group is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less.

[0016] Examples of the monovalent hydrocarbon group include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining two or more groups selected from an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.

[0017] The aliphatic hydrocarbon group may be linear or branched. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 20, more preferably 1 to 15, even more preferably 1 to 10, and particularly preferably 1 to 4. The aliphatic hydrocarbon group is preferably an alkyl group or an alkenyl group, more preferably an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and a butyl group.

[0018] The alicyclic hydrocarbon group may be, for example, monocyclic or polycyclic. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 15, and even more preferably 4 to 10. The alicyclic hydrocarbon group is preferably a cycloalkyl group or a cycloalkenyl group, and more preferably a cycloalkyl group. Examples of cycloalkyl groups include a cyclohexyl group and a methylcyclohexyl group.

[0019] The aromatic hydrocarbon group may be, for example, monocyclic or polycyclic. In the case of a polycyclic group, two or more rings may form a condensed ring. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 15, and even more preferably 6 to 10. The aromatic hydrocarbon group is preferably an aryl group. Examples of the aryl group include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.

[0020] Examples of groups that combine two or more groups selected from aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include groups consisting of an alicyclic hydrocarbon group and an aliphatic hydrocarbon group, such as a cyclohexylmethyl group and a methylcyclohexylmethyl group; and groups consisting of an aromatic hydrocarbon group and an aliphatic hydrocarbon group, such as a benzyl group and a phenylethyl group.

[0021] R 1 and R 2 In view of excellent pot life and the like, the monovalent organic group in is preferably an aliphatic hydrocarbon group, more preferably an alkyl group, still more preferably an alkyl group having 1 to 20 carbon atoms, even more preferably an alkyl group having 1 to 15 carbon atoms, particularly preferably an alkyl group having 1 to 10 carbon atoms, and most preferably an alkyl group having 1 to 4 carbon atoms.

[0022] The polyaspartic acid ester is preferably a compound represented by formula (2). [ka]

[0023] The meanings of the symbols in formula (2) are as follows: X in formula (2) is an n-valent organic group. The n-valent organic group is preferably an n-valent hydrocarbon group. The n-valent hydrocarbon group preferably has 1 to 50 carbon atoms, more preferably 3 to 40 carbon atoms, even more preferably 5 to 30 carbon atoms, still more preferably 5 to 20 carbon atoms, and particularly preferably 10 to 16 carbon atoms.

[0024] Examples of the n-valent hydrocarbon group include an n-valent aliphatic hydrocarbon group, an n-valent alicyclic hydrocarbon group, an n-valent aromatic hydrocarbon group, and an n-valent group formed by combining two or more groups selected from aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. Among these groups, a divalent hydrocarbon group is preferred.

[0025] The n-valent aliphatic hydrocarbon group may be, for example, linear or branched. The number of carbon atoms in the n-valent aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10. Examples of the n-valent aliphatic hydrocarbon group include groups derived from alkanes (in the case of divalent groups, alkanediyl groups) and groups derived from alkenes (in the case of divalent groups, alkenediyl groups), with groups derived from alkanes being preferred. Examples of the alkanediyl group include methanediyl, ethanediyl, propanediyl, butanediyl, pentanediyl, and hexanediyl groups.

[0026] The n-valent alicyclic hydrocarbon group may be, for example, monocyclic or polycyclic. The number of carbon atoms in the n-valent alicyclic hydrocarbon group is preferably 3 to 30, more preferably 4 to 20, and even more preferably 5 to 10. Examples of the n-valent alicyclic hydrocarbon group include groups derived from cycloalkanes (cycloalkanediyl groups in the divalent case) and groups derived from cycloalkenes (cycloalkenediyl groups in the divalent case), with groups derived from cycloalkanes being preferred. Examples of the cycloalkanediyl group include cyclohexanediyl and methylcyclohexanediyl groups.

[0027] The n-valent aromatic hydrocarbon group may be, for example, monocyclic or polycyclic. In the case of a polycyclic group, two or more rings may form a fused ring. The number of carbon atoms in the n-valent aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. Examples of the n-valent aromatic hydrocarbon group include groups derived from aromatic hydrocarbons (arylene groups in the case of divalent groups). Examples of the arylene group include a phenylene group, a toluenediyl group, a xylenediyl group, and a naphthylene group.

[0028] Examples of the n-valent group formed by combining two or more groups selected from aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include an n-valent group formed by combining an aliphatic hydrocarbon group with an alicyclic hydrocarbon group, and an n-valent group formed by combining an aliphatic hydrocarbon group with an aromatic hydrocarbon group.

[0029] Examples of n-valent groups that combine an aliphatic hydrocarbon group and an alicyclic hydrocarbon group include a dicyclohexylmethane-4,4'-diyl group and a bis(methylcyclohexyl)methane-4,4'-diyl group. Examples of n-valent groups that combine an aliphatic hydrocarbon group and an aromatic hydrocarbon group include a diphenylmethane-4,4'-diyl group and a 2,2-diphenylpropane-4,4'-diyl group.

[0030] As the n-valent organic group for X, from the viewpoint of, for example, providing an excellent pot life for the resulting composition, an n-valent alicyclic hydrocarbon group or an n-valent group combining an aliphatic hydrocarbon group and an alicyclic hydrocarbon group is more preferable, and an n-valent group combining an aliphatic hydrocarbon group and an alicyclic hydrocarbon group is particularly preferable.

[0031] X in formula (2) is preferably an n-valent organic group obtained by removing the amino groups (-NH2) of a polyamine having n amino groups (hereinafter also referred to as an "organic group derived from a polyamine").

[0032] The polyamine in the organic group of X is preferably an aliphatic and / or alicyclic polyamine, from the viewpoint of providing a composition with an excellent pot life, etc. In other words, the organic group of X is preferably an organic group derived from an aliphatic and / or alicyclic polyamine. Examples of the polyamines include ethylenediamine, 1,2-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,5-diamino-2-methylpentane, 1,6-diaminohexane, 2,5-diamino-2,5-dimethylhexane, 2,2,4-trimethyl-1,6-diaminohexane, 2,4,4-trimethyl-1,6-diaminohexane, 1,11-diaminoundecane, 1,12-diamino-2, ... Nododecane, 1-amino-3,3,5-trimethyl-5-aminomethylcyclohexane, 2,4-hexahydrotolylenediamine, 2,6-hexahydrotolylenediamine, 2,4'-diaminodicyclohexylmethane, 4,4'-diaminodicyclohexylmethane, 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane, and 2,4,4'-triamino-5-methyldicyclohexylmethane.

[0033] R in equation (2) 1 and R 2 are R in Equation (1), respectively. 1 and R 2 is synonymous with.

[0034] n in formula (2) and n in the n-valent are integers of 2 or more. From the viewpoint of ease of synthesis or availability of the polyaspartic acid ester, n is preferably an integer of 2 to 6, more preferably an integer of 2 to 4, and even more preferably 2.

[0035] Specific examples of polyaspartic acid esters include compounds represented by formulas (2-1) to (2-3). Among these, compounds represented by formula (2-2) or formula (2-3) are preferred, and compounds represented by formula (2-3) are more preferred.

[0036] [ka]

[0037] In one embodiment, the polyaspartic acid ester is liquid and tends to have a lower viscosity than, for example, a polyol compound. By using the polyaspartic acid ester, the content of diluting organic solvent in the composition can be reduced, and for example, a high-solids composition can be easily obtained.

[0038] The molecular weight of the polyaspartic acid ester is preferably 2,000 or less, more preferably 1,500 or less, even more preferably 1,000 or less, still more preferably 800 or less, and particularly preferably 600 or less.

[0039] As the polyaspartic acid ester, commercially available products may be used. Polyaspartic acid esters can be produced, for example, by reacting a primary polyamine represented by formula (a) with a maleic acid ester or a fumaric acid ester represented by formula (b). X-[NH2] n (a) R 1 OOC-CH=CH-COOR 2 (b) X and n in formula (a) have the same meanings as X and n in formula (2), respectively. R in formula (b) 1 and R 2 are R in Equation (1), respectively. 1 and R 2 is synonymous with. Examples of primary polyamines include the polyamines described above in the description of the organic group for X. Examples of maleate esters or fumarate esters include dimethyl maleate, diethyl maleate, dipropyl maleate, dibutyl maleate, dimethyl fumarate, diethyl fumarate, dipropyl fumarate, and dibutyl fumarate.

[0040] The composition of the present disclosure may contain two or more polyaspartic acid esters. The first agent may contain two or more types of polyaspartic acid esters. The content of the polyaspartic acid ester in the composition of the present disclosure is preferably 3 to 60 mass%, more preferably 5 to 50 mass%, even more preferably 8 to 40 mass%, and particularly preferably 10 to 35 mass%, based on the mass of the solid content of the composition. The content of the polyaspartic acid ester in the first agent may be set so that the content of the polyaspartic acid ester in the solid content of the composition of the present disclosure falls within the above range.

[0041] The solid content of a substance (e.g., a composition or ingredient) refers to the heating residue when the substance is dried in an incubator at 125°C for 1 hour. Specifically, the heating residue is the residue of the sample (including the residue adhering to the wire) obtained by weighing out a 1.0 g sample of the substance in question onto a flat-bottomed dish, spreading it evenly using a wire of known mass, and drying it in an incubator at 1 atmosphere and 125°C for 1 hour.

[0042] <Cardanol compounds> The composition of the present disclosure contains a cardanol-based compound. The first and / or third components contain a cardanol-based compound. Although the reason is unclear, the presence of the cardanol-based compound in the curing reaction system between the polyaspartic acid ester and the polyisocyanate compound (specifically, the reaction system between the amino group of the polyaspartic acid ester and the isocyanate group of the polyisocyanate compound) can enhance the drying and curing properties of the composition. Therefore, the composition of the present disclosure has a fast curing rate, for example, even at low to room temperatures.

[0043] Therefore, the cardanol-based compound is suitable as a curing accelerator for the curing reaction between a polyaspartic acid ester and a polyisocyanate compound. That is, the cardanol-based compound can be used as a curing accelerator in the curing reaction between a polyaspartic acid ester and a polyisocyanate compound.

[0044] The cardanol-based compound may be cardanol, a cardanol derivative, or a mixture thereof. Among these, cardanol is preferred from the viewpoint of the above-mentioned curing reactivity.

[0045] Cardanol is a compound represented by formula (3). [ka]

[0046] In formula (3), R 3 is a saturated or unsaturated hydrocarbon group having 15 carbon atoms. The hydrocarbon group may be linear or branched, but is preferably linear. The hydrocarbon group preferably has 0 to 3 C=C double bonds, more preferably 1 to 3, still more preferably 1 to 2, and particularly preferably 2. When the hydrocarbon group has two or more C=C double bonds, non-conjugated double bonds are preferred.

[0047] R 3 is preferably -(CH2) 14 -CH3, -(CH2)7-CH=CH-(CH2)5-CH3, -(CH2)7-CH=CH-CH2-CH=CH-(CH2)2-CH3, -(CH2)7-CH=CH-CH2-CH=CH-CH2-CH=CH2, -(CH2)6-CH=CH-(CH2)6-CH3, -(CH2)6-CH=CH-CH2-CH=CH-(CH2)3-CH3, or -(CH2)6-CH=CH-CH2-CH=CH-(CH2)2-CH=CH2 and More preferably, -(CH2)6-CH=CH-(CH2)6-CH3, -(CH2)6-CH=CH-CH2-CH=CH-(CH2)3-CH3, or -(CH2)6-CH=CH-CH2-CH=CH-(CH2)2-CH=CH2 and More preferably -(CH2)6-CH=CH-CH2-CH=CH-(CH2)3-CH3 is.

[0048] Specifically, cardanol is 3-pentadecylphenol, 3-[pentadec-8-enyl]phenol, 3-[pentadeca-8,11-dienyl]phenol, 3-[pentadeca-8,11,14-trienyl]phenol, 3-[pentadec-7-enyl]phenol, 3-[pentadeca-7,10-dienyl]phenol, and 3-[pentadeca-7,10,14-trienyl]phenol Examples include:

[0049] Among these, at least one selected from 3-[pentadeca-7-enyl]phenol, 3-[pentadeca-7,10-dienyl]phenol, and 3-[pentadeca-7,10,14-trienyl]phenol is preferred, with 3-[pentadeca-7,10-dienyl]phenol (see the formula below) being particularly preferred.

[0050] [ka]

[0051] Cardanol may be a single compound, for example, R 3 It may also be a mixture of two or more compounds which differ in the number and / or position of unsaturated groups in the hydrocarbon group.

[0052] As used herein, a cardanol derivative refers to a compound having a structure derived from cardanol, specifically a modified form in which part of the cardanol structure is substituted with another group. As the cardanol derivative, a compound represented by formula (4) is preferred.

[0053] [ka]

[0054] The meanings of the symbols in formula (4) are as follows: R 3 is R in Equation (3). 3 is synonymous with. R 4 is a hydroxy group, a carboxy group, an alkoxy group (e.g., methoxy and ethoxy), an acyl group (e.g., acetyl and propionyl), an amino group, or a substituted or unsubstituted hydrocarbon group.

[0055] Examples of hydrocarbon groups include alkyl groups such as methyl, ethyl, propyl, and butyl groups, and alkenyl groups such as allyl groups, with alkyl groups being preferred. The number of carbon atoms in the hydrocarbon group is preferably 20 or less, more preferably 16 or less, even more preferably 10 or less, still more preferably 6 or less, and particularly preferably 4 or less. The hydrocarbon group may be partially substituted with a substituent, such as a hydroxy group, a carboxy group, an alkoxy group, an acyl group, an amino group, an epoxy group, an ether bond, or an ester bond.

[0056] m is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 or 2. When m is 2 or more, a plurality of R 4 may be the same group or different groups.

[0057] Specific examples of cardanol derivatives include anacardic acid, cardol, and 2-methyl cardol.

[0058] The cardanol derivative may be a single compound, for example, R 3 The number and position of unsaturated groups in the hydrocarbon group of R 4 It may also be a mixture of two or more compounds in which one or more selected from the types and numbers of:

[0059] As the cardanol-based compound, either a synthetic product or a natural product may be used. The cardanol-based compound may be, for example, a component obtained from natural cashew nut shell liquid or industrial cashew nut shell liquid, a derivative of the component, or a mixture of two or more of these components. Cashew nut shell liquid is a liquid containing a phenol derivative extracted from the shells that encase cashew nuts. Industrial cashew nut shell liquid is a liquid obtained by subjecting natural cashew nut shell liquid to heat treatment. For example, natural cashew nut shell liquid or industrial cashew nut shell liquid may be used when preparing the first agent and / or the third agent. These shell liquids contain cardanol-based compounds.

[0060] In one embodiment, the cardanol-based compounds may include 25 to 45 mass% of cardanol-based compounds having one C=C double bond, 10 to 30 mass% of cardanol-based compounds having two C=C double bonds, 30 to 50 mass% of cardanol-based compounds having three C=C double bonds, and 0 to 10 mass% of cardanol-based compounds having no C=C double bonds.

[0061] The compositions of the present disclosure may contain two or more cardanol-based compounds. The first agent and / or the third agent may contain two or more types of cardanol-based compounds. The content of the cardanol-based compound in the composition of the present disclosure is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, even more preferably 3% by mass or more, and particularly preferably 5% by mass or more or 5.5% by mass or more, based on the mass of the solid content of the composition, from the viewpoint of the aforementioned accelerating effect on dry curing properties. The content of the cardanol-based compound in the composition of the present disclosure is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 12% by mass or less, and particularly preferably 10% by mass or less, based on the mass of the solid content of the composition, from the viewpoint of the excellent pot life of the composition and the excellent mechanical strength of the coating film formed. The content is preferably 0.1 to 20% by mass, more preferably 0.5 to 15% by mass, even more preferably 1 to 12% by mass, even more preferably 3 to 10% by mass, and particularly preferably 5 to 10% by mass or 5.5 to 10% by mass, from the viewpoint of the balance between dry curing properties and pot life. The content ratio of the cardanol-based compound in the first agent and / or the third agent may be set so that the content ratio of the cardanol-based compound in the solid content of the composition of the present disclosure falls within the above range.

[0062] <Polyol compounds> The composition of the present disclosure may further contain a polyol compound. The first and / or third components may further contain a polyol compound. However, the term "polyol compound" as used herein refers to a polymer having two or more hydroxy groups. The above composition containing a polyol compound in addition to a polyaspartic acid ester and a cardanol-based compound tends to exhibit excellent drying and curing properties while having a longer usable life. For example, after mixing the first and second components, or after mixing the first, second, and third components, the viscosity of the composition increases over time due to reactions between the components in the composition. The time during which the coating workability using the above composition remains within an acceptable range is generally referred to as the usable life.

[0063] Examples of polyol compounds include (meth)acrylic polyols, polyester polyols, polyether polyols, polycarbonate polyols, polyurethane polyols, and polyolefin polyols. Examples of polyolefin polyols include polybutadiene, hydrogenated polybutadiene, polyisoprene, and hydrogenated polyisoprene, each of which has two or more hydroxy groups.

[0064] Among polyol compounds, (meth)acrylic polyol is preferred. In this specification, (meth)acrylic means acrylic and / or methacrylic, and expressions such as (meth)acrylate described below have the same meaning.

[0065] Examples of (meth)acrylic polyols include homopolymers or copolymers of (meth)acrylic compounds having hydroxy groups, copolymers of (meth)acrylic compounds having hydroxy groups with other compounds copolymerizable with the (meth)acrylic compounds, and modified products of these polymers.

[0066] Examples of the (meth)acrylic compound having a hydroxy group include 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, and hydroxybutyl (meth)acrylate. One or more types of the (meth)acrylic compound having a hydroxy group may be used.

[0067] Examples of the other compounds include unsaturated carboxylic acid compounds such as (meth)acrylic acid, maleic acid, and fumaric acid; unsaturated carboxylic acid ester compounds such as diethyl maleate and diethyl phthalate; methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, neopentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, stearyl (meth)acrylate, isostearyl acrylate, and methyl (meth)acrylate. (Meth)acrylic acid alkyl esters such as allyl (meth)acrylate, cetyl (meth)acrylate, and lauryl (meth)acrylate; (meth)acrylic compounds having fluorine atoms such as 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, and 2-(perfluorooctyl)ethyl (meth)acrylate; isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclohexyl (meth)acrylate, (meth)acrylic compounds having an alicyclic structure such as cyclopentanyl (meth)acrylate and dicyclopentenyloxyethyl (meth)acrylate; (meth)acrylic compounds having an ether bond such as polyethylene glycol mono(meth)acrylate, methoxyethyl (meth)acrylate, methoxybutyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, and methoxypolyethylene glycol (meth)acrylate; (meth)acrylic compounds having an aromatic ring such as benzyl (meth)acrylate; 2-ethyl-2-methyl-[1,3]-dioxolan-4-yl-methyl (meth)acrylate; (meth)acrylic compounds having an amino group such as dimethylaminoethyl (meth)acrylate; (meth)acrylamide compounds such as N,N-dimethyl(meth)acrylamide and N,N-diethyl(meth)acrylamide; and vinyl compounds such as styrene, α-methylstyrene, vinyl acetate, vinyl benzoate, vinyl toluene, acrylonitrile, methacrylonitrile, vinylpyridine, vinylpyrrolidone, and vinyl chloride. The other compounds may be used alone or in combination of two or more.

[0068] Examples of the modified product include alkyd resin-modified (meth)acrylic polyol and fatty acid-modified (meth)acrylic polyol. Among these, alkyd resin-modified (meth)acrylic polyol is preferred. The modified product refers to a resin in which the proportion of structural units derived from the modified component is less than 50% by mass.

[0069] The alkyd resin-modified (meth)acrylic polyol can be obtained by a conventionally known method. The resin may be synthesized, for example, using a homopolymer or copolymer of a (meth)acrylic compound having a hydroxy group and an alkyd resin. The resin may be synthesized, for example, using a copolymer of a (meth)acrylic compound having a hydroxy group and the other compounds listed above and an alkyd resin. The resin may be synthesized, for example, using a (meth)acrylic compound having a hydroxy group, an alkyd resin, and, if necessary, the other compounds listed above.

[0070] The alkyd resin can be obtained by a conventionally known method, and is preferably a resin obtained by polycondensation of a conventionally known (semi-)drying oil or (semi-)drying oil fatty acid, a conventionally known acid component, and a conventionally known polyhydric alcohol component.

[0071] The (meth)acrylic polyol preferably has a styrene skeleton, from the viewpoints that its glass transition temperature (Tg) can be easily adjusted, a coating film excellent in mechanical strength can be easily obtained, etc. As such a (meth)acrylic polyol, a (meth)acrylic polyol having a styrene skeleton and an alkyd resin-modified (meth)acrylic polyol having a styrene skeleton are preferred.

[0072] The glass transition temperature (Tg) of the (meth)acrylic polyol is preferably 10°C or higher, more preferably 20°C or higher, and even more preferably 30°C or higher, from the viewpoint of easily obtaining a coating film with excellent coating film hardness. The Tg is preferably 80°C or lower, more preferably 70°C or lower, and even more preferably 60°C or lower, from the viewpoint of easily obtaining a coating film with excellent crack resistance. The Tg of the (meth)acrylic polyol is the temperature (°C) at the onset value of DSC during heating, obtained by measuring the change in heat quantity in the range of -50 to 150°C at a heating rate of 20°C / min using a differential scanning calorimeter (DSC) in a nitrogen atmosphere.

[0073] From the viewpoint of easily obtaining a coating material with excellent drying and curing properties, the weight-average molecular weight (Mw) of the (meth)acrylic polyol is preferably 3,000 to 40,000, more preferably 4,000 to 35,000, and even more preferably 5,000 to 30,000. Mw is a value measured using gel permeation chromatography (GPC) and converted into standard polystyrene.

[0074] The hydroxyl value of the (meth)acrylic polyol is preferably 10 to 300 mgKOH / g, more preferably 20 to 200 mgKOH / g, even more preferably 30 to 150 mgKOH / g, and particularly preferably 40 to 100 mgKOH / g, from the viewpoint of easily obtaining a coating material that exhibits excellent drying and curing properties. The hydroxyl value of the (meth)acrylic polyol is the number of milligrams of potassium hydroxide required to neutralize acetic acid bonded to hydroxyl groups (hydroxy groups) when 1 g of a sample is acetylated, and is measured in accordance with the neutralization titration method of JIS K0070:1992.

[0075] The composition of the present disclosure may contain one or more polyol compounds. The first agent and / or the third agent may contain one or more polyol compounds.

[0076] When the composition of the present disclosure contains a polyol compound, the content of the polyol compound in the composition is preferably 1 to 30 mass%, more preferably 3 to 25 mass%, and even more preferably 5 to 20 mass%, based on the mass of the solid content of the composition, from the viewpoint of the balance between drying and curing properties and usable life. The content of the polyol compound in the first and / or third parts may be set so that the content of the polyol compound in the solid content of the composition of the present disclosure falls within the above range. When the composition of the present disclosure contains a polyol compound, the content of the polyol compound per 100 parts by mass of the polyaspartic acid ester is preferably more than 0 parts by mass and not more than 200 parts by mass, more preferably 10 to 150 parts by mass, even more preferably 20 to 120 parts by mass, still more preferably 30 to 100 parts by mass, and particularly preferably 40 to 80 parts by mass, from the viewpoint of the balance between drying and curing properties and usable life.

[0077] Other ingredients The composition of the present disclosure, or the first and / or third agents, may further contain components (other components) other than the polyaspartic acid ester, cardanol-based compound, and polyol compound. Examples of other components include pigments, additives, and organic solvents. Examples of additives include thixotropic agents (also known as anti-sagging agents or anti-settling agents), dispersants, light stabilizers, surface conditioners, antifoaming agents, thickeners, plasticizers, surfactants, mildew inhibitors, preservatives, and UV absorbers. It is preferable that the other components are not polyisocyanate compounds.

[0078] The above components may be used alone or in combination of two or more. The composition of the present disclosure, or the first and / or third agents, may contain one or more other components. The other components may be contained in at least one agent selected from the first agent and the second agent described below, or may be contained in at least one agent selected from the first agent and the second and third agents described below. For example, the other components may be contained in the first agent, the third agent, the second agent described below, or all of the first, second, and third agents.

[0079] (pigment) Examples of pigments include color pigments and extender pigments. Examples of color pigments include inorganic pigments such as carbon black, titanium oxide, red iron oxide, iron hydroxide, and ultramarine; and organic pigments such as phthalocyanine blue and phthalocyanine green. Examples of extender pigments include barium sulfate, calcium carbonate, potassium feldspar, kaolin, clay, talc, mica, bentonite, magnesium carbonate, and silica.

[0080] When the composition of the present disclosure contains a pigment, the content of the pigment in the composition is preferably 20 to 70 mass %, more preferably 30 to 60 mass %, based on the mass of the solid content of the composition, from the viewpoint of easily obtaining a coating film that is well-balanced in terms of flexibility and adhesion to the primer coating film. The content of the pigment in the first and / or third agents may be set so that the content of the pigment in the solid content of the composition of the present disclosure falls within the above range. The same applies to the content of each component in the following explanation.

[0081] When the composition of the present disclosure contains a pigment, the pigment volume concentration (hereinafter also referred to as "PVC") of the composition is preferably 5 to 35% by volume, more preferably 15 to 25% by volume, from the viewpoint of easily obtaining a coating film that has a good balance between flexibility and adhesion to the primer coating film.

[0082] PVC refers to the concentration of the total volume of pigments in a composition relative to the volume of solids in the composition. Specifically, PVC can be calculated using the following formula: PVC [%] = total volume of all pigments in the composition × 100 / Volume of solids in the composition

[0083] The volume of the solid content in the composition can be calculated from the mass and true density of the solid content of the composition. The mass and true density of the solid content may be measured values ​​or may be values ​​calculated from the raw materials used. The volume of the pigment can be calculated from the mass and true density of the pigment used. The mass and true density of the pigment may be measured values ​​or may be values ​​calculated from the raw materials used. For example, the pigment and other components may be separated from the solid content of the composition, and the mass and true density of the separated pigment may be measured.

[0084] (thixotropic agent) Examples of thixotropic agents include organic clay salts such as stearates, lecithin salts, and alkylsulfonates of Al, Ca, or Zn; clays such as bentonite clay and hectorite clay; organically modified versions of such clays (e.g., organically modified hectorite clay); waxes such as oxidized polyethylene wax, ethylene-vinyl acetate wax, polyamide wax, and hydrogenated castor oil wax; and synthetic finely powdered silica.

[0085] When the composition of the present disclosure contains a thixotropic agent, the content of the thixotropic agent in the composition is preferably 0.1 to 2 mass %, more preferably 0.3 to 1.5 mass %, based on the mass of the solid content of the composition, from the viewpoint of being able to easily obtain a coating film with excellent smoothness, etc.

[0086] (dispersant) Examples of dispersants include copolymers having pigment-adsorbing groups (pigment-affinity groups) and compatible chains. Examples of pigment-adsorbing groups include carboxyl groups, phosphate groups, amino groups, salt groups thereof, and ammonium salt groups. Examples of compatible chains include fatty acids, polyaminos, polyethers, polyesters, polyurethanes, and poly(meth)acrylates.

[0087] When the composition of the present disclosure contains a dispersant, the content of the dispersant in the composition is preferably 0.01 to 1 mass %, more preferably 0.1 to 0.5 mass %, based on the mass of the solid content of the composition, from the viewpoint of being able to easily obtain a coating film with excellent smoothness, etc.

[0088] (light stabilizer) Examples of light stabilizers include hindered amine light stabilizers (HALS). Examples of hindered amine light stabilizers include bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, methyl(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, 2,4-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-(2-hydroxyethylamine)-1,3,5-triazine, and decanedioic acid bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl)ester.

[0089] When the composition of the present disclosure contains a light stabilizer, the content of the light stabilizer in the composition is preferably 0.1 to 2 mass %, and more preferably 0.3 to 1 mass %, based on the mass of the solid content of the composition, from the viewpoint of being able to easily obtain a coating film with excellent weather resistance, etc.

[0090] (surface conditioner) Examples of surface conditioners include (meth)acrylic surface conditioners and silicone surface conditioners. When the composition of the present disclosure contains a surface conditioner, the content of the surface conditioner in the composition is preferably 0.1 to 2 mass %, more preferably 0.3 to 1 mass %, based on the mass of the solid content of the composition, from the viewpoint of being able to improve the appearance of the coating film, etc.

[0091] (organic solvent) Examples of organic solvents include aromatic, aliphatic, alicyclic, ketone, ether, ester, and alcohol organic solvents. Specific examples of organic solvents include aromatic hydrocarbon solvents such as toluene and xylene, aliphatic or alicyclic hydrocarbon solvents such as mineral spirits and cyclohexane, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, ether or ester solvents such as methyl acetate, ethyl acetate, butyl acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate, and alcohol solvents such as n-butyl alcohol and isopropyl alcohol.

[0092] The content of the organic solvent in the composition of the present disclosure is not particularly limited. The organic solvent may be used in an amount that takes into consideration recent environmental conservation and environmental load. The content of the organic solvent in the composition of the present disclosure is, based on the mass of the composition, preferably 50 mass% or less, more preferably 40 mass% or less, even more preferably 30 mass% or less, even more preferably 20 mass% or less, particularly preferably 15 mass% or less, and may be 0 mass% or more, for example, 2 mass% or more or 4 mass% or more.

[0093] <Second agent> The second agent, which constitutes one embodiment of the composition of the present disclosure, contains a polyisocyanate compound. The compositions of the present disclosure contain a polyisocyanate compound. The composition or second agent of the present disclosure may further contain other ingredients as described above.

[0094] <Polyisocyanate compounds> The polyisocyanate compound has two or more isocyanate groups in one molecule. The number of isocyanate groups in the polyisocyanate compound is preferably 2 to 6, and more preferably 2 to 4. Examples of the polyisocyanate compound include aliphatic polyisocyanates, alicyclic polyisocyanates, and aromatic polyisocyanates.

[0095] Examples of aliphatic polyisocyanates include aliphatic diisocyanates, and specific examples include linear aliphatic diisocyanates such as trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, and hexamethylene diisocyanate; and branched aliphatic diisocyanates such as 2,2,4-trimethylhexamethylene diisocyanate. Examples of the alicyclic polyisocyanate include alicyclic diisocyanates such as cyclopentane diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, and hydrogenated toluene diisocyanate. Examples of aromatic polyisocyanates include aromatic diisocyanates such as phenylene diisocyanate, xylylene diisocyanate, tolylene diisocyanate, naphthalene diisocyanate, dianisidine diisocyanate, tetramethylxylylene diisocyanate, 4,4'-diphenylmethane diisocyanate, and 3,3'-dimethyldiphenyl-4,4'-diisocyanate.

[0096] Examples of the polyisocyanate compound include dimers or trimers (for example, biuret-modified products, isocyanurate-modified products) or allophanate products of aliphatic polyisocyanates, alicyclic polyisocyanates, or aromatic polyisocyanates.

[0097] Among the polyisocyanate compounds, at least one selected from hexamethylene diisocyanate (HDI), isophorone diisocyanate, an isocyanurate-modified product of hexamethylene diisocyanate (HDI), and an isocyanurate-modified product of isophorone diisocyanate is preferred.

[0098] The composition of the present disclosure may contain two or more polyisocyanate compounds. The second agent may contain two or more types of polyisocyanate compounds. The content of the polyisocyanate compound in the composition of the present disclosure is preferably 5 to 35 mass%, more preferably 10 to 30 mass%, and even more preferably 13 to 25 mass%, based on the mass of the solid content of the composition. The content of the polyisocyanate compound in the second agent may be set so that the content of the polyisocyanate compound in the solid content of the composition of the present disclosure falls within the above range.

[0099] In the composition of the present disclosure, the ratio (NCO / (NH+OH)) of the isocyanate group equivalent (NCO) of the polyisocyanate compound to the sum (NH+OH) of the amino group equivalent of the polyaspartic acid ester and the hydroxy group equivalent of the polyol compound is preferably 0.5 to 2.0, more preferably 0.7 to 1.5, and even more preferably 0.9 to 1.3. A composition having the above ratio exhibits, for example, an excellent balance between dry curing properties and usable life. In calculating the above ratio, the polyol compound is an optional component.

[0100] Other ingredients The second agent may further contain the other components described above. Examples of the other components include pigments, additives, and organic solvents. Examples of the additives include thixotropic agents, dispersants, light stabilizers, surface conditioners, antifoaming agents, thickeners, plasticizers, surfactants, mildew inhibitors, preservatives, and UV absorbers.

[0101] The above components may be used alone or in combination of two or more. Specific examples of each of the above components are the same as those listed in the columns for the first and third parts. The second agent may contain one or more other components.

[0102] <Agents other than those listed above> In one embodiment, the composition of the present disclosure is a multi-component composition having a first component and a second component, or a multi-component composition having a first component, a second component, and a third component, such as a two-component composition consisting of a first component and a second component, or a three-component composition consisting of a first component, a second component, and a third component. In one embodiment, the first component may be a so-called main component, and the second component may be a so-called curing agent. The third component may also be a curing accelerator. The composition may further contain other agents (hereinafter also referred to as "other agents") in addition to the above-mentioned agents depending on the components used. The other agents may be, for example, an agent containing a polyol compound and, if necessary, other components, or an agent containing other components.

[0103] <Method for preparing the composition> For example, when the first agent is a mixture, it can be prepared by mixing the respective components to be blended. For example, when the second agent is a mixture, it can be prepared by mixing the respective components to be blended. For example, when the third agent is a mixture, it can be prepared by mixing the respective components to be blended. When mixing, each component may be added at once or in multiple portions.

[0104] Each of the first, second, third, and other agents is usually preserved, stored, or transported in a separate container. At the time of use (e.g., immediately before painting), the first, second, and other agents, or the first, second, and third agents, and other agents, if necessary, are mixed together to form a mixture. In other words, the above-mentioned agents can be considered components of a kit for preparing the composition (mixture) of the present disclosure, which contains a polyaspartic acid ester, a cardanol-based compound, and a polyisocyanate compound.

[0105] The composition (mixture, e.g., paint) of the present disclosure can be prepared, for example, by mixing a first agent, a second agent, and other agents used as needed, or a first agent, a second agent, a third agent, and other agents used as needed. After or during this preparation, the composition may be diluted before use depending on the coating method, etc. All descriptions in this specification, except for those related to such dilution, are descriptions of the composition before dilution.

[0106] The mixing can be performed using conventionally known devices such as mixers, dispersers, and stirrers. Examples of such devices include dispersers, mixing / dispersion mills, mortar mixers, rolls, paint shakers, and homogenizers. Mixing can be performed while heating or cooling, depending on the season or environment.

[0107] In recent years, regulations regarding the content of volatile organic compounds (VOCs) have become stricter from the viewpoints of environmental conservation and working environment safety. From this viewpoint, the composition may be a high-solids composition. The volumetric solid content of a high-solids composition is preferably 60% or more, more preferably 70% or more, and even more preferably 75% or more, 80% or more, 85% or more, or 90% or more. The upper limit of the volumetric solid content in the composition is not particularly limited, but may be, for example, 99%, 98%, or 96%. The volumetric solid content (also referred to as volume solids) in a composition is measured in accordance with ISO 3233:1998.

[0108] The content of volatile organic compounds (VOCs) such as organic solvents in the composition of the present disclosure is preferably 400 g / L or less, more preferably 300 g / L or less, and even more preferably 200 g / L or less, from the viewpoint of environmental conservation and working environment safety. The lower the VOC content in the composition, the better, but the content may be, for example, 1 g / L or more, 10 g / L or more, 30 g / L or more, or 50 g / L or more. The VOC content in the composition may be, for example, 1 to 400 g / L.

[0109] The VOC content in the composition is calculated based on the following formula using the specific gravity and solids concentration of the composition, which are described below. VOC content (g / L) = Composition specific gravity x 1000 x (100-solid content concentration) / 100

[0110] The specific gravity of the composition (g / mL) is a value calculated by filling a specific gravity cup with the above composition (the mixture immediately after mixing the various ingredients) at a temperature of 23°C and measuring the mass of the composition. The solid content concentration (mass%) is a value calculated from the amount of the heating residue of the composition. As described above, the solid content of the composition means the heating residue when the composition is dried in an incubator at 125°C for 1 hour.

[0111] The composition of the present disclosure can be suitably applied to, for example, a substrate. Examples of the material of the substrate include steel (e.g., iron, steel, ferroalloy, carbon steel, mild steel, alloy steel), non-ferrous metal (e.g., zinc, aluminum, copper, brass, zinc plating, zinc thermal spraying), and stainless steel (e.g., SUS304, SUS410), as well as plastic (e.g., polypropylene, polyamide, polycarbonate, polyurethane, polyester, polystyrene, vinyl chloride resin), ceramic, glass, and concrete. Among these, steel or stainless steel is preferred. Specific examples of the substrate include structures such as ships (e.g., decks, superstructures, or outer hulls of ships), bridges, marine structures (e.g., marine buoys, undersea pipelines), plants, tanks, and containers, with steel or stainless steel structures being preferred.

[0112] The composition of the present disclosure can be used, for example, as a paint composition, coating material, ink, or adhesive, or as a material for forming molded articles such as films and sheets. Applications of the coating material include, for example, electronic device components, clothing, furniture or home appliances, daily necessities, building materials, and automotive components. The composition of the present disclosure is suitable as a coating composition such as a topcoat coating composition. For example, the composition of the present disclosure may be used to form a topcoat coating film on an undercoat coating film for the purpose of enhancing design or weather resistance. Furthermore, since polyaspartic acid esters have excellent corrosion resistance, the composition of the present disclosure may be used for metal corrosion prevention applications.

[0113] [Coatings and painted products] The coating of the present disclosure is formed using the composition of the present disclosure. The coating film is considered to contain a polyurea compound formed by the reaction of a polyaspartic acid ester with a polyisocyanate compound. Therefore, the coating film has, for example, excellent mechanical strength. When the composition further contains a polyol compound, the coating film is considered to further contain a polyurethane compound or a polyurea / polyurethane compound formed by the reaction of a polyol compound with a polyisocyanate compound. In one embodiment, the coating film has a polyurea structure and may further contain a polyurethane structure, if desired.

[0114] The coating film of the present disclosure has a dry thickness of preferably 20 to 200 μm, more preferably 50 to 100 μm.

[0115] The coated article of the present disclosure has a substrate and a coating film of the present disclosure provided on the substrate. The details of the substrate are as described above. The substrate may be a substrate that has been subjected to a pretreatment such as a cleaning treatment to remove rust, dirt, paint (old paint film), etc., adhering to the substrate, or a blasting treatment. The coating film of the present disclosure contained in the coated article may be one layer or two or more layers.

[0116] The coated article may have a primer coating film between the substrate and the coating film of the present disclosure for the purpose of improving adhesion or corrosion resistance, etc. The coated article of this embodiment has a substrate, a primer coating film, and a coating film of the present disclosure, in that order. The primer coating film may be one layer or two or more layers.

[0117] The term "undercoat coating film" includes not only known undercoat coating films (primer coating films) in the narrow sense, but also known coating films called intermediate coating films. Primer coating films include, for example, coating films formed from various primer compositions such as epoxy resin-based or inorganic zinc-based. Intermediate coating films include, for example, coating films formed from various intermediate coating paint compositions such as epoxy resin-based or polyurethane resin-based.

[0118] The thickness of the undercoat coating is preferably 50 to 500 μm, more preferably 100 to 350 μm, in terms of dry film thickness.

[0119] The coating film and primer coating film of the present disclosure can be formed, for example, by applying the composition or primer coating of the present disclosure to an object (e.g., a substrate, a substrate on which a primer coating film has been formed), and drying the applied coating. Coating methods include, for example, brush coating, air spray coating, airless spray coating, roll coater coating, and immersion. Coating films with the above thicknesses may be formed by a single coating, or by two or more coatings. Drying conditions include, for example, a drying time of preferably 1 hour to 30 days, more preferably 1 hour to 7 days, and a drying temperature of preferably 5 to 40°C, more preferably 10 to 30°C, and may be, for example, ambient temperature.

[0120] The coated article of the present disclosure can be produced, for example, by a production method having a step of applying the composition of the present disclosure to a substrate and a step of drying the applied composition to form a coating film. The coated article of the present disclosure can be produced, for example, by a production method including the steps of forming a primer coating film on a substrate, applying a composition of the present disclosure to the primer coating film, and drying the applied composition to form a coating film.

[0121] [Example of situation] The present disclosure relates to, for example, the following [1] to

[15] . [1] A first agent containing a polyaspartic acid ester and a cardanol-based compound; a second agent containing a polyisocyanate compound; or a first agent containing a polyaspartic acid ester; a second agent containing a polyisocyanate compound; a third agent containing a cardanol-based compound; A composition comprising: [2] A composition containing a polyaspartic acid ester, a cardanol-based compound, and a polyisocyanate compound. [3] In the composition, based on the mass of the solid content of the composition, the content of the polyaspartic acid ester is 3 to 60 mass %, The content of the cardanol-based compound is 0.1 to 20% by mass. The composition according to [1] or [2] above. [4] The composition according to any one of [1] to [3] above, wherein the first agent and / or the third agent, or the composition, further contains a polyol compound. [5] The composition according to [4], wherein the first agent and / or the third agent, or the composition, contains at least a (meth)acrylic polyol as the polyol compound. [6] The composition according to [4] or [5], wherein the content of the polyol compound in the composition is 1 to 30 mass % based on the mass of the solid content of the composition. [7] The composition according to any one of [1] to [6], which is a two-component composition consisting of the first agent and the second agent, or a three-component composition consisting of the first agent, the second agent, and the third agent. [8] The composition according to any one of [1] to [7] above, which is a coating composition. [9] The composition according to [8], wherein the coating composition is a high-solids composition having a solid content of 60% or more by volume.

[10] The composition according to [8] or [9] above, which is for use in ships.

[11] A curing accelerator containing a cardanol-based compound for the curing reaction of a polyaspartic acid ester and a polyisocyanate compound.

[12] Use of a cardanol-based compound as a curing accelerator in the curing reaction of a polyaspartic acid ester and a polyisocyanate compound.

[13] A coating film formed from the composition according to any one of the above [1] to

[10] .

[14] A coated article comprising a substrate and the coating film according to

[13] provided on the substrate.

[15] The coated article according to

[14] , further comprising an undercoat coating film between the substrate and the coating film. [Example]

[0122] The composition of the present disclosure will be described in more detail below using examples. However, the contents of the present disclosure are not limited to the following examples or comparative examples. In the following description, "parts by mass" will be simply referred to as "parts" unless otherwise specified.

[0123] [raw materials] The raw materials used to prepare the compositions of the Examples or Comparative Examples are listed below. Polyaspartic acid ester Feispartic F-520, manufactured by Feiyang, Compound represented by the above formula (2-3), solid content: 100% by mass Acrylic polyol-containing products APO-320, manufactured by Ohtake Meishin Chemical Co., Ltd. Solid content (active ingredient): 55% by mass, organic solvent: 45% by mass ·Alkyd-modified acrylic polyol-containing products APO-380, manufactured by Ohtake Meishin Chemical Co., Ltd. Solid content (active ingredient): 70% by mass, organic solvent: 30% by mass Cardanol NX-2026, made by Cardolite, solid content: 100% by mass Methyl isobutyl ketone MIBK, KH manufactured by Neochem Co., Ltd. Color pigments Titanium white (titanium dioxide), Ti-Pure R-960, manufactured by Chemours Inc. · Extender pigment Calcium Carbonate, Calcium Carbonate Super SS, Manufactured by Maruo Calcium Co., Ltd. Anti-sagging agent amorphous silica, Aerosil R972, manufactured by Nippon Aerosil Co., Ltd. Dispersant BYK-2152, manufactured by BYK Japan Co., Ltd., solid content: 100% by mass Light stabilizers HALS, HS Ester 292, Toyokuni Oil Mills, solid content: 100% by mass Acrylic surface conditioner L-1983N, Kusumoto Chemicals Co., Ltd., solid content: 100% by mass Polyisocyanate compounds HDI Isocyanurate, Tolonate HDT, manufactured by Vencorex, solid content: 100% by weight Butyl acetate Butyl acetate, manufactured by KH Neochem Co., Ltd.

[0124] [Example 1] A first part was prepared by mixing and dispersing 41 parts of polyaspartic acid ester, 5 parts of cardanol, 3 parts of methyl isobutyl ketone, 39 parts of color pigment, 10 parts of extender pigment, 0.7 parts of anti-sagging agent, 0.3 parts of dispersant, 0.5 parts of light stabilizer, and 0.5 parts of acrylic surface conditioner using a paint shaker. A second part was prepared by mixing and stirring 90 parts of a polyisocyanate compound and 10 parts of butyl acetate. In this way, a two-part paint composition having a first part and a second part was obtained. 76 parts of the first part and 24 parts of the second part were mixed to prepare the paint.

[0125] [Examples 2 to 6 and Comparative Examples 1 to 3] The first and second agents were prepared in the same manner as in Example 1, except that the types and amounts of the components constituting the first and second agents were changed as shown in Table 1. The first and second agents thus prepared were mixed to obtain the mixing ratios (mass %) shown in Table 1 to prepare the paints.

[0126] [Dry curability] The drying and curing properties of each paint (mixture of first and second parts) in the Examples and Comparative Examples were evaluated using a drying time recorder (TP Giken Co., Ltd., RC-type paint drying time measuring device) in accordance with the measurement method (Drying tests, method A) of ISO 9117-4:2012(E). Specifically, the paint was applied to a rectangular piece of glass measuring 300 mm x 25 mm using an applicator with a 0.15 μm gap, and the drying and curing times (hard-dry time and through-dry time) were measured in accordance with the measurement method. Measurements were performed at 23°C and 50% RH and 5°C and 50% RH. At the through-dry time, the coated surface was touched with a finger, and if no tack was felt, the tack was rated "A", and if tack was felt, the tack was rated "B".

[0127] [Pot life] 300 g of each paint (mixture of first and second parts) of the Examples or Comparative Examples was weighed into a container, and 15 g of thinner (butyl acetate) was added immediately after the mixing. The viscosity of the paint (initial viscosity, paint temperature 23°C) was measured immediately after the addition. After the addition, the paint was stored at 23°C and 50% RH for 30 minutes. After the 30-minute storage, the viscosity of the paint (viscosity after 30 minutes) was measured. The viscosity was measured using a viscometer (BROOKFIELD KU-2 Viscometer, manufactured by BROOKFIELD Corporation) at an ambient temperature of 23°C and 50% RH. The viscosity increase rate was calculated from the initial viscosity and the viscosity after 30 minutes according to the following formula. Viscosity increase rate (%) = viscosity after 30 minutes / initial viscosity x 100

[0128] [Table 1]

Claims

1. a first agent containing a polyaspartic acid ester and a cardanol-based compound; a second agent containing a polyisocyanate compound; or a first agent containing a polyaspartic acid ester; a second agent containing a polyisocyanate compound; a third agent containing a cardanol-based compound; A composition comprising:

2. A composition containing a polyaspartic acid ester, a cardanol-based compound, and a polyisocyanate compound.

3. In the composition, based on the mass of the solid content of the composition, The content of the polyaspartic acid ester is 3 to 60 mass %, The content of the cardanol-based compound is 0.1 to 20% by mass. The composition according to claim 1 or 2.

4. The composition according to claim 1 , wherein the first agent and / or the third agent further contains a polyol compound.

5. The composition according to claim 4 , wherein the first agent and / or the third agent contains at least a (meth)acrylic polyol as the polyol compound.

6. The composition according to claim 4, wherein the content of the polyol compound in the composition is 1 to 30 mass% based on the mass of the solid content of the composition.

7. The composition according to claim 1, which is a two-component composition consisting of the first agent and the second agent, or a three-component composition consisting of the first agent, the second agent, and the third agent.

8. 3. The composition of claim 1 or 2, which is a coating composition.

9. The composition according to claim 8, wherein the coating composition is a high-solids composition having a solids volume content of 60% or more.

10. The composition of claim 8 for use in marine applications.

11. A curing accelerator containing a cardanol-based compound for the curing reaction of a polyaspartic acid ester and a polyisocyanate compound.

12. Use of a cardanol-based compound as a curing accelerator in the curing reaction of a polyaspartic acid ester and a polyisocyanate compound.

13. A coating film formed from the composition according to claim 1 or 2.

14. A substrate; The coating film according to claim 13 provided on the substrate; A painted product having the above characteristics.

15. The coated article according to claim 14, further comprising a primer coating between the substrate and the coating.

Citation Information

Patent Citations

  • Polyaspartic coating composition, coating film, and coated article

    WO2018163953A1