Coating agent, coating film, article, method and production method

Abstract

Provided is a coating agent that is able to yield a novel coating film.　The present invention relates to a coating agent that contains a compound which has, in the molecule, a betaine structure and a structure represented by formula (1). (R1 is an organic group or a group having an Si-O bond, R2 is an organic group or a group having an Si-O bond, R1 and R2 may be the same as, or different from, each other, n is an integer of 2 or higher, multiple R1 moieties may be the same as, or different from, each other, and multiple R2 moieties may be the same as, or different from, each other.)

Description

Coating agent, coating film, article, method, and manufacturing method

[0001] The present invention relates to a coating agent, a coating film, an article, a method, and a manufacturing method.

[0002] Conventionally, a coating agent has been applied to the surface of a mirror or glass, and the surface has been covered with a coating film to prevent adhesion of dirt. For example, it is known that even if dirt temporarily adheres to a hydrophilic coating film, the dirt can be easily removed by washing with water.

[0003] For example, Patent Document 1 describes a coating agent and a coating film containing a compound having a betaine structure. The coating film described in Patent Document 1 improves adhesion to a substrate by forming a glass-like coating layer composed of tetraalkoxysilane and a betaine structure layer. The coating film can be obtained by applying a glass-like coating agent to a substrate surface and curing it, and then applying a betaine structure agent to the surface of the glass-like coating layer and curing it (two-component configuration). Alternatively, the coating film can be obtained by mixing the glass-like coating agent and the betaine structure agent, applying the mixture to the substrate surface, allowing it to naturally separate into two layers, and waiting for it to harden (one-component configuration). Patent Document 1 also describes that the betaine structure moieties are oriented on the surface of the betaine structure layer, which is polarized with positive charges on the nitrogen atoms and negative charges on the oxygen atoms, exhibiting hydrophilicity and antifouling properties.

[0004] Japanese Patent Application Laid-Open No. 2020-49901

[0005] At least one object of the present invention is to provide a coating agent that can provide a novel coating film.

[0006] The object of the present invention is to provide a compound having the formula (1): (R １ is an organic group or a group having an Si—O bond, and R ２ is an organic group or a group having an Si—O bond, and R １ and R ２ may be the same or different, n is an integer of 2 or more, and a plurality of R１ may be the same or different, and multiple R ２ [2] The coating agent according to the above [1], wherein the betaine structure is a carbobetaine structure, a sulfobetaine structure, or a phosphobetaine structure; [3] The coating agent according to the above [1], wherein the compound is represented by formula (2): , formula (3): , formula (4): , or formula (5): (R ３ is hydrogen or a methyl group, and R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４(aromatic ring, phenylene group)); [4] The coating agent according to any one of the above [1] to [3], wherein the structure represented by formula (1) is obtainable by hydrolyzing a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent, followed by a condensation reaction; [5] The coating agent according to any one of the above [1] to [4], wherein the mass ratio of the structure represented by formula (1) to the compound ((mass of the structure represented by formula (1)) / (mass of the compound)) is 1 / 100 to 99.9 / 100; [6] The coating agent according to any one of [3] to [5], wherein the mass ratio of the structure represented by formula (2), (3), (4) or (5) to the compound ((mass of the structure represented by formula (2), (3), (4) or (5)) / (mass of the compound)) is 0.1 / 100 to 99 / 100; [7] A coating film obtained by applying the coating agent according to any one of [1] to [6] to a target object and drying it; [8] An article provided with a coating film obtained by applying the coating agent according to any one of [1] to [6] to a target object and drying it; [9] A method for applying the coating agent according to any one of [1] to [6] to a target object;

[10] A step of hydrolyzing a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent, followed by a condensation reaction to obtain a siloxane oligomer or a siloxane polymer, and combining the obtained siloxane oligomer or siloxane polymer with a compound of formula (2): , formula (3): , formula (4): , or formula (5): (R ３ is hydrogen or a methyl group, and R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C６ H ４ (aromatic ring, phenylene group)) and having a silanol group and / or a group capable of reacting with and bonding to a functional group derived from a silane coupling agent contained in a siloxane oligomer or a siloxane polymer;

[11] a method for producing a siloxane coupling agent by reacting a compound having a structure represented by the formula (2): , formula (3): , formula (4): , or formula (5): (R ３ is hydrogen or a methyl group, and R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)) and a compound having a group capable of reacting with and bonding to a silanol group and / or a functional group of the silane coupling agent;

[12] The method according to

[10] or

[11] above, comprising a step of applying a coating agent containing the compound obtained by the reacting step to an object;

[13] A method comprising a step of hydrolyzing a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent, and subjecting the hydrolysis to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer, and reacting the obtained siloxane oligomer or siloxane polymer with a compound of formula (2): , formula (3): , formula (4): , or formula (5): (R ３ is hydrogen or a methyl group, and R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)) and having a group capable of reacting with a silanol group and / or a functional group derived from a silane coupling agent contained in a siloxane oligomer or a siloxane polymer to bond thereto;

[14] a method for producing a coating agent, comprising a step of reacting a dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or a silane coupling agent with a compound of formula (2): , formula (3): , formula (4): , or formula (5): (R ３ is hydrogen or a methyl group, and R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (an aromatic ring, a phenylene group)) and having a silanol group and / or a group capable of reacting with and bonding to a functional group possessed by the silane coupling agent;

[0007] According to an embodiment of the present invention, a coating agent capable of forming a novel coating film can be provided.

[0008] The components of the coating agent of the present invention, the production method, and the method for forming the coating film will be described below.

[0009] The coating agent of the present invention has a structure represented by the formula (1): (R１ is an organic group or a group having an Si—O bond, and R ２ is an organic group or a group having an Si—O bond, and R １ and R ２ may be the same or different, n is an integer of 2 or more, and a plurality of R １ may be the same or different, and multiple R ２ may be the same or different) and a betaine structure (hereinafter referred to as compound A).

[0010] R in formula (1) １ The organic group in R is not particularly limited, but is preferably an alkyl group or an alkoxy group. １ The organic group may be a group derived from a silane coupling agent, that is, an organic group contained as part of a silane coupling agent.

[0011] R in formula (1) ２ The organic group in R is not particularly limited, but is preferably an alkyl group or an alkoxy group. ２ The organic group may be a group derived from a silane coupling agent, that is, an organic group contained as part of a silane coupling agent.

[0012] A silanol group derived from a silane coupling agent undergoes dehydration condensation with another dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, or a silanol group derived from a silane coupling agent, thereby obtaining a structure represented by formula (1) in which a group derived from a silane coupling agent is introduced as an organic group bonded to a silicon atom.

[0013] R in formula (1) １ or R ２ The alkyl group used in the above may be linear or branched, and may have an unsaturated bond. In addition, some of the hydrogen atoms in the alkyl group may be substituted with atoms other than hydrogen atoms or with substituents.

[0014] R in formula (1) １ or R ２The number of carbon atoms in the alkyl group used in formula (1) is preferably 1 or more, and more preferably 2 or more. １ or R ２ The alkyl group employed preferably has 50 or less carbon atoms, and more preferably 20 or less carbon atoms.

[0015] R in formula (1) １ or R ２ The alkoxy group used in may have a linear or branched structure, may have an unsaturated bond, and may have some of the hydrogen atoms substituted with atoms other than hydrogen atoms or with substituents.

[0016] R in formula (1) １ or R ２ The number of carbon atoms in the alkoxy group used in formula (1) is preferably 1 or more, and more preferably 2 or more. １ or R ２ The number of carbon atoms of the alkoxy group used in R in formula (1) is preferably 8 or less, and more preferably 4 or less. １ or R ２ The alkoxy group employed in is preferably a methoxy group or an ethoxy group.

[0017] R １ or R ２ may be a group having an Si—O bond. In other words, the structure represented by formula (1) may have a linear chain of continuous Si—O bonds, or the chain of continuous Si—O bonds may have a branch. Furthermore, the structure represented by formula (1) may have a three-dimensional network structure.

[0018] In formula (1), n ​​is an integer of 2 or more. In formula (1), n ​​is preferably 2 or more, more preferably 3 or more, and even more preferably 5 or more. In formula (1), n ​​is preferably 5,000 or less, more preferably 3,000 or less, and even more preferably 2,000 or less.

[0019] The structure represented by formula (1) is preferably one that can be obtained by hydrolyzing at least a dialkoxydialkylsilane, a trialkoxyalkylsilane, and / or a tetraalkoxysilane, followed by a condensation reaction. In particular, the structure represented by formula (1) is preferably one that can be obtained by hydrolyzing a tetraalkoxysilane, followed by a condensation reaction. When a tetraalkoxysilane is reacted with a dialkoxydialkylsilane and / or a trialkoxyalkylsilane, the ratio of the mass of the tetraalkoxysilane to the total mass of the dialkoxydialkylsilane, trialkoxyalkylsilane, and tetraalkoxysilane is preferably 0.2 or more, more preferably 0.5 or more.

[0020] Furthermore, the structure represented by formula (1) is preferably one that can be obtained by hydrolyzing at least a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent, followed by a condensation reaction.

[0021] Known silane coupling agents can be used. When the silane coupling agent is reacted with a dialkoxydialkylsilane, a trialkoxyalkylsilane, and / or a tetraalkoxysilane, the mass ratio of the silane coupling agent to the total mass of the dialkoxydialkylsilane, the trialkoxyalkylsilane, the tetraalkoxysilane, and the silane coupling agent is preferably 0.005 or more, more preferably 0.01 or more. The mass ratio of the silane coupling agent to the total mass of the dialkoxydialkylsilane, the trialkoxyalkylsilane, the tetraalkoxysilane, and the silane coupling agent is preferably 0.5 or less, more preferably 0.25 or less.

[0022] The structure represented by formula (1) can also be obtained by reacting only a dialkoxydialkylsilane, a trialkoxyalkylsilane, and / or a tetraalkoxysilane without using a silane coupling agent. The structure represented by formula (1) can also be obtained by reacting only a silane coupling agent without using a dialkoxydialkylsilane, a trialkoxyalkylsilane, or a tetraalkoxysilane.

[0023] A catalyst may be used when hydrolyzing and condensing the dialkoxydialkylsilane, dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or silane coupling agent. The use of a catalyst can accelerate the hydrolysis reaction and the condensation reaction. The catalyst used is not particularly limited. For example, a mineral acid such as hydrochloric acid, nitric acid, sulfuric acid, or phosphoric acid, or an organic acid such as formic acid or acetic acid may be used as the catalyst. The amount of the catalyst used can also be appropriately designed.

[0024] The term "betaine structure" refers to a structure in which a positively charged atom and a negatively charged atom are located in non-adjacent positions within the same molecule (or within the same structure), and no dissociable hydrogen atom is bonded to the positively charged atom, so that the molecule (or structure) as a whole does not have an electric charge.

[0025] The betaine structure of Compound A is preferably a carbobetaine structure, a sulfobetaine structure, or a phosphobetaine structure. A sulfobetaine structure refers to a structure having a sulfo group instead of a carboxy group in a carbobetaine structure. A phosphobetaine structure refers to a structure having a phosphate group instead of a carboxy group in a carbobetaine structure.

[0026] In carbobetaine structures, the carboxy group carries the negative charge, in sulfobetaine structures, the sulfo group carries the negative charge, and in phosphobetaine structures, the phosphate group carries the negative charge.

[0027] The betaine structure of Compound A may have an ammonium cation structure, a sulfonium cation structure, or a phosphonium cation structure as a positive charge. The betaine structure of Compound A preferably has a quaternary ammonium cation structure as a positive charge.

[0028] Compound A is represented by formula (2): , formula (3): , formula (4): , or formula (5): (R ３ is hydrogen or a methyl group, and R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)). More specifically, compound A preferably contains a structure represented by formula (1) and a structure represented by formula (2), (3), (4) or (5). For example, compound A is preferably obtained by reacting a compound having a structure represented by formula (1) with a compound having a structure represented by formula (2), (3), (4) or (5). In this case, it is preferable that a functional group at the end of the compound having a structure represented by formula (2), (3), (4) or (5) reacts with a silanol group derived from an alkoxysilyl group of the compound having a structure represented by compound (1), or a functional group derived from a silane coupling agent of the compound having a structure represented by compound (1) to bond.

[0029] R of formula (2), (3), (4) or (5) ４ The organic group used in is not particularly limited and can be appropriately designed. For example, ４The organic group used in R may be an alkyl group, and the number of carbon atoms therein is not particularly limited. A portion of the hydrogen atoms in the alkyl group may be substituted with atoms other than hydrogen atoms or with substituents. ４ The organic group employed in R may be saturated or may have an unsaturated bond. ４ The organic group employed in formula (2), (3), (4) or (5) may have a functional group bonded to any carbon atom. ４ The organic group employed may include a plurality of different types of organic groups.

[0030] In addition, R in formula (2), (3), (4) or (5) ４ The organic group employed in formula (2), (3), (4) or (5) includes a group having a betaine structure. ４ Regarding the betaine structure contained in the organic group employed in formula (2), (3), (4), or (5), the above description of the betaine structure can be adopted to the extent necessary. ４ The betaine structure employed in is preferably a carbobetaine structure, a sulfobetaine structure, or a phosphobetaine structure.

[0031] In formula (2), (3), (4), or (5), m is an integer of 2 or more. In formula (2), (3), (4), or (5), m is preferably 2 or more, more preferably 5 or more, and even more preferably 10 or more. In formula (2), (3), (4), or (5), m is preferably 50,000 or less, more preferably 20,000 or less, and even more preferably 10,000 or less.

[0032] The structure represented by formula (2) can be, for example, a structure represented by formula (6): (R ３ is hydrogen or a methyl group, and R ５ is an organic group, k is an integer of 1 or more, j is an integer of 1 or more, and a plurality of R ３ may be the same or different, and R ５ When there are multiple R ５may be the same or different), where k and j are equal to or less than m.

[0033] Formula (6) represents a structure in which a (meth)acrylic acid ester unit having a group having a betaine structure and a (meth)acrylic acid ester unit having an arbitrary organic group are block copolymerized. However, for example, the (meth)acrylic acid ester unit having a group having a betaine structure and the (meth)acrylic acid ester unit having an arbitrary organic group may be randomly copolymerized, alternatingly copolymerized, or graft copolymerized.

[0034] R in formula (6) ５ The organic group used in is not particularly limited and can be appropriately designed. For example, ５ The organic group used in R may be an alkyl group, and the number of carbon atoms therein is not particularly limited. A portion of the hydrogen atoms in the alkyl group may be substituted with atoms other than hydrogen atoms or with substituents. ５ The organic group employed in R may be saturated or may have an unsaturated bond. ５ The organic group used in formula (6) may have a functional group bonded to any carbon atom. ５ The organic group employed may include a plurality of different types of organic groups.

[0035] R in formula (6) ５ The number of carbon atoms in the alkyl group used in formula (6) is preferably 1 or more. ５ The number of carbon atoms in the alkyl group employed is preferably 8 or less, and more preferably 4 or less.

[0036] The mass ratio of the structure represented by formula (1) to compound A ((mass of the structure represented by formula (1)) / (mass of compound A)) is preferably 1 / 100 or more, more preferably 5 / 100 or more, and even more preferably 10 / 100 or more. Furthermore, the mass ratio of the structure represented by formula (1) to compound A ((mass of the structure represented by formula (1)) / (mass of compound A)) is preferably 99.9 / 100 or less, more preferably 95 / 100 or less, and even more preferably 90 / 100 or less. When compound A is obtained by reacting a compound having a structure represented by formula (1) with a compound having a structure represented by formula (2), (3), (4), or (5), the mass ratio of the structure represented by formula (1) to compound A can be determined by dividing the mass of the compound having the structure represented by formula (1) by the total mass of the compound having the structure represented by formula (1) and the compound having the structure represented by formula (2), (3), (4), or (5).

[0037] The mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of compound A)) is preferably 0.1 / 100 or more, more preferably 5 / 100 or more, and even more preferably 10 / 100 or more. Furthermore, the mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of compound A)) is preferably 99 / 100 or less, more preferably 95 / 100 or less, and even more preferably 90 / 100 or less. When compound A is obtained by reacting a compound having a structure represented by formula (1) with a compound having a structure represented by formula (2), (3), (4), or (5), the mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A can be determined by dividing the mass of the compound having a structure represented by formula (2), (3), (4), or (5) by the total mass of the compound having a structure represented by formula (1) and the compound having a structure represented by formula (2), (3), (4), or (5).

[0038] For example, when the betaine structure of compound A is a carbobetaine structure, the mass ratio of the structure represented by formula (1) to compound A ((mass of the structure represented by formula (1)) / (mass of compound A)) is preferably 10 / 100 or more, more preferably 15 / 100 or more, and even more preferably 20 / 100 or more. Furthermore, for example, when the betaine structure of compound A is a carbobetaine structure, the mass ratio of the structure represented by formula (1) to compound A ((mass of the structure represented by formula (1)) / (mass of compound A)) is preferably 80 / 100 or less, more preferably 75 / 100 or less, and even more preferably 70 / 100 or less.

[0039] For example, when the betaine structure of compound A is a carbobetaine structure, the mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of compound A)) is preferably 20 / 100 or more, more preferably 25 / 100 or more, and even more preferably 30 / 100 or more. Furthermore, for example, when the betaine structure of compound A is a carbobetaine structure, the mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of compound A)) is preferably 90 / 100 or less, more preferably 85 / 100 or less, and even more preferably 80 / 100 or less.

[0040] For example, when the betaine structure of compound A is a sulfobetaine structure, the mass ratio of the structure represented by formula (1) to compound A ((mass of the structure represented by formula (1)) / (mass of compound A)) is preferably 1 / 100 or more, more preferably 5 / 100 or more, and even more preferably 10 / 100 or more. Furthermore, for example, when the betaine structure of compound A is a sulfobetaine structure, the mass ratio of the structure represented by formula (1) to compound A ((mass of the structure represented by formula (1)) / (mass of compound A)) is preferably 99.9 / 100 or less, more preferably 95 / 100 or less, and even more preferably 90 / 100 or less.

[0041] For example, when the betaine structure of compound A is a sulfobetaine structure, the mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of compound A)) is preferably 0.1 / 100 or more, more preferably 5 / 100 or more, and even more preferably 10 / 100 or more. Furthermore, for example, when the betaine structure of compound A is a sulfobetaine structure, the mass ratio of the structure represented by formula (2), (3), (4), or (5) to compound A ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of compound A)) is preferably 99 / 100 or less, more preferably 95 / 100 or less, and even more preferably 90 / 100 or less.

[0042] Compound A may be a compound having a structure represented by formula (1) and a structure obtained by copolymerizing monomers capable of constituting a structure represented by formula (2), (3), (4), or (5) in any combination.

[0043] Compound A can be obtained by the following steps: hydrolyzing a dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or a silane coupling agent, followed by a condensation reaction to obtain a siloxane oligomer or siloxane polymer (i.e., a compound having a structure represented by formula (1)); and reacting the obtained siloxane oligomer or siloxane polymer with a compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with and bonding to a silanol group. Hereinafter, the compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with and bonding to a silanol group will be referred to as compound B.

[0044] Compound B has a group capable of reacting with and bonding to a silanol group. Compound B preferably has, for example, a group capable of reacting with and bonding to a silanol group at the end of a compound having a structure represented by formula (2), (3), (4), or (5). The group capable of reacting with and bonding to a silanol group is, for example, an alkoxysilyl group. This alkoxysilyl group is not particularly limited, but is preferably a methoxysilyl group or an ethoxysilyl group. When the obtained siloxane oligomer or siloxane polymer reacts with compound B, the alkoxysilyl group of the obtained siloxane oligomer or siloxane polymer is hydrolyzed to generate a silanol group, and this generated silanol group is bonded to a group (e.g., an alkoxysilyl group) capable of reacting with and bonding to the silanol group of compound B by dehydration condensation, thereby obtaining compound A.

[0045] Compound A can be obtained by the following steps: hydrolyzing a silane coupling agent and a dialkoxydialkylsilane, trialkoxyalkylsilane, and / or tetraalkoxysilane, and subjecting them to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer; and reacting a compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with and bonding to the functional group derived from the silane coupling agent contained in the siloxane oligomer or the siloxane polymer. Hereinafter, the compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with and bonding to the functional group derived from the silane coupling agent contained in the siloxane oligomer or the siloxane polymer is referred to as Compound C.

[0046] Compound C has a group capable of reacting with and bonding to a functional group derived from a silane coupling agent contained in a siloxane oligomer or siloxane polymer. The functional group derived from a silane coupling agent is not particularly limited, but examples thereof include an epoxy group, an amino group, an isocyanate group, a mercapto group, a carboxyl group, a vinyl group, and a (meth)acrylic group. The group capable of reacting with and bonding to a functional group derived from a silane coupling agent is not particularly limited, as long as it is a group capable of reacting with a functional group such as an epoxy group, an amino group, an isocyanate group, a mercapto group, a carboxyl group, a vinyl group, or a (meth)acrylic group.

[0047] Compound A can also be obtained by reacting a dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or silane coupling agent with a compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with a silanol group to form a bond. Compound A can also be obtained by reacting a silane coupling agent with a compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with a silanol group to form a bond, or by reacting a silane coupling agent with a dialkoxydialkylsilane, trialkoxyalkylsilane, and / or tetraalkoxysilane and a compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with a silanol group to form a bond. Compound A reacted with these silane coupling agents has a structure represented by formula (2), (3), (4) or (5), and the compound having a group capable of reacting with and bonding to a silanol group is bonded to the structure represented by formula (1) by dehydration condensation of the silanol group, so that functional groups other than the alkoxysilyl group derived from the silane coupling agent remain unreacted.

[0048] Furthermore, compound A can also be obtained by a step of reacting a silane coupling agent and a dialkoxydialkylsilane, trialkoxyalkylsilane, and / or tetraalkoxysilane with a compound having a structure represented by formula (2), (3), (4), or (5) and having a group capable of reacting with and bonding to a functional group (a functional group other than an alkoxysilyl group) possessed by the silane coupling agent. In this case, the functional group derived from the silane coupling agent contained in a siloxane oligomer or siloxane polymer obtained by hydrolysis and condensation polymerization of the silane coupling agent and the dialkoxydialkylsilane, trialkoxyalkylsilane, and / or tetraalkoxysilane reacts with and bonds to a functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5).

[0049] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is an epoxy group (glycidyl group), the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) can be an amino group, a thiol group (mercapto), a carboxylic anhydride, an imidazole group, an isocyanate group, a phenol group, a carboxyl group, a hydroxyl group, or the like, which can react with and bond to the epoxy group (glycidyl group).

[0050] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is an amino group, the functional group possessed by the compound having a structure represented by formula (2), (3), (4) or (5) can be a halogen atom (chlorine atom), maleimide, epoxy group, carbodiimide, carboxylic acid, carboxylic acid ester, isocyanate group, etc. When an amino group reacts with a halogen atom, the halogen atom is eliminated to obtain compound A. When an amino group reacts with a carboxylic acid, water is eliminated to obtain compound A. When an amino group reacts with a carboxylic acid ester, alcohol is eliminated to obtain compound A.

[0051] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a vinyl group, the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) can be a vinyl group, a hydroxyl group, a silyl group, or the like.

[0052] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a (meth)acrylic group, the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) can be a (meth)acrylic group, a styryl group, or the like.

[0053] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is an isocyanate group, a hydroxyl group, a carboxyl group, or the like can be used as the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5).

[0054] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a mercapto group, an isocyanate group, a mercapto group, a vinyl group, etc. can be used as the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5). When a mercapto group reacts with another mercapto group, hydrogen is eliminated to obtain compound A.

[0055] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a carboxyl group, a thiol group, a carbodiimide group, a hydroxyl group, etc. can be used as the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5). When a carboxyl group and a thiol group react, water is eliminated to obtain compound A. When a carboxyl group and a hydroxyl group react, water is eliminated to obtain compound A.

[0056] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a hydroxyl group, a chlorine atom, a methylol group, a carbodiimide group, etc. can be used as the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5). When a hydroxyl group reacts with a chlorine atom, hydrogen chloride is eliminated to obtain compound A. When a hydroxyl group reacts with a methylol group, water is eliminated to obtain compound A.

[0057] Furthermore, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a carbonyl group, a hydrazide group, an amino group, or the like can be used as the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5). When the carbonyl group reacts with the hydrazide group, water is eliminated to obtain compound A. When the carbonyl group reacts with the amino group, water is eliminated to obtain compound A.

[0058] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is an epoxy group (glycidyl group), the functional group possessed by the silane coupling agent can be an amino group, a thiol group (mercapto), a carboxylic acid anhydride, an imidazole group, an isocyanate group, a phenol group, a carboxyl group, a hydroxyl group, or the like.

[0059] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4) or (5) is an amino group, the functional group possessed by the silane coupling agent can be a halogen (chlorine), maleimide, epoxy group, carbodiimide, carboxylic acid, carboxylic acid ester, isocyanate group, etc. When an amino group reacts with a halogen, the halogen is eliminated to obtain compound A. When an amino group reacts with a carboxylic acid, water is eliminated to obtain compound A. When an amino group reacts with a carboxylic acid ester, an alcohol is eliminated to obtain compound A.

[0060] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is a vinyl group, the functional group possessed by the silane coupling agent may be a vinyl group, a hydroxyl group, a silyl group, or the like.

[0061] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is a (meth)acrylic group, the functional group possessed by the silane coupling agent can be a (meth)acrylic group, a styryl group, or the like.

[0062] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is an isocyanate group, the functional group possessed by the silane coupling agent can be a hydroxyl group, a carboxyl group, or the like.

[0063] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is a mercapto group, the functional group possessed by the silane coupling agent can be an isocyanate group, a mercapto group, a vinyl group, etc. When a mercapto group reacts with another mercapto group, hydrogen is eliminated to obtain compound A.

[0064] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is a carboxyl group, the functional group possessed by the silane coupling agent can be a thiol, a carbodiimide, a hydroxyl group, or the like. When a carboxyl group reacts with a thiol group, water is eliminated to obtain compound A. When a carboxyl group reacts with a hydroxyl group, water is eliminated to obtain compound A.

[0065] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is a hydroxyl group, the functional group possessed by the silane coupling agent can be a chlorine atom, a methylol group, a carbodiimide group, or the like. When a hydroxyl group reacts with a chlorine atom, hydrogen chloride is eliminated to obtain compound A. When a hydroxyl group reacts with a methylol group, water is eliminated to obtain compound A.

[0066] Furthermore, for example, when the functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5) is a carbonyl group, a hydrazide group, an amino group, or the like can be used as the functional group possessed by the silane coupling agent. When the carbonyl group reacts with the hydrazide group, water is eliminated to obtain compound A. When the carbonyl group reacts with the amino group, water is eliminated to obtain compound A.

[0067] A catalyst may be used when reacting a siloxane oligomer or a siloxane polymer with a compound having a structure represented by formula (2), (3), (4), or (5). The type of catalyst is not particularly limited. Any catalyst may be used depending on the type of functional group possessed by the silane coupling agent and the type of functional group possessed by the compound having a structure represented by formula (2), (3), (4), or (5).

[0068] The temperature when reacting a siloxane oligomer or siloxane polymer with a compound having a structure represented by formula (2), (3), (4), or (5) is not particularly limited and can be appropriately designed. The temperature when reacting a siloxane oligomer or siloxane polymer with a compound having a structure represented by formula (2), (3), (4), or (5) is, for example, preferably 5° C. or higher, more preferably 20° C. or higher. Furthermore, the temperature when reacting a siloxane oligomer or siloxane polymer with a compound having a structure represented by formula (2), (3), (4), or (5) is, for example, preferably 80° C. or lower, more preferably 70° C. or lower.

[0069] A reaction terminator may be used to terminate the reaction between the siloxane oligomer or siloxane polymer and the compound having a structure represented by formula (2), (3), (4), or (5). The type of reaction terminator is not particularly limited, and any reaction terminator can be used.

[0070] Compound A contains organic and inorganic groups and has a complex structure, making it difficult and impractical to identify the structure, properties, etc. of the compound.

[0071] (Solvent) The coating agent of the present invention contains a solvent. As the solvent, water or a water-containing alcohol-based solvent, and glycol ether can be used. Examples of alcohol-based solvents include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-pentanol, i-pentanol, 2-methylbutanol, sec-pentanol, t-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, 3-heptanol, and n-octanol. Examples of suitable alcohol-based solvents include lower aliphatic alcohol-based solvents such as 2-ethylhexanol, sec-octanol, n-nonyl alcohol, 2,4,6-dimethylheptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec-heptadecyl alcohol, phenol, cyclohexanol, methylcyclohexanol, 3,3,5-trimethylcyclohexanol, benzyl alcohol, and diacetone alcohol. Examples of glycol ethers include ethylene glycol monobutyl ether and derivatives thereof, propylene glycol monoalkyl ethers, ethylene glycol monoalkyl ethers, diethylene glycol monobutyl ether, and derivatives thereof. These alcohol-based solvents and glycol ethers can be used alone or in combination. The compound can be stably dispersed by using water or water-containing alcohol-based solvents or glycol ethers.

[0072] In the coating agent of the present invention, the amount of solvent is preferably adjusted so that the solid content is 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1.0% by mass or more. If the solid content is less than 0.1% by mass, a large amount of coating agent is required to form a coating film of the desired thickness, which tends to reduce work efficiency. The amount of solvent is preferably adjusted so that the solid content is 30% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less. If the solid content exceeds 30% by mass, the storage stability of the coating agent tends to decrease.

[0073] (Other Additives) The coating agent of the present invention may contain surfactants such as leveling agents for the purpose of smoothing the coating film, thickeners for the purpose of preventing cissing, and coloring pigments depending on the application. Other additives may be added within a range that does not affect the hydrophilicity of the coating film formed by the coating agent of the present invention.

[0074] (Method for producing coating agent) The coating agent of the present invention can be obtained, for example, by obtaining compound A as described above, stirring compound A and a solvent, and dispersing compound A in the solvent. When an additive is added to the coating agent, compound A, the additive, and the solvent may be stirred, and compound A and the additive may be dispersed in the solvent.

[0075] (Method for forming a coating film) Methods for forming a coating film on a substrate using the coating agent of the present invention include a method for applying the coating agent to the surface of the substrate and a method for immersing the substrate in the coating agent. The method for applying the coating agent to the surface of the substrate is particularly preferred because it is simple, inexpensive, and allows the required film thickness to be easily controlled.

[0076] The coating method is not particularly limited, and any known technique may be used, such as spin coating, dipping, spraying, flow coating, bar coating, roller coating, reverse coating, flexography, or printing.

[0077] In order to improve the adhesion between the substrate and the coating film, the surface of the substrate may be pretreated by corona discharge treatment, glow discharge treatment, treatment with ionizing active rays such as ultraviolet light, electron beams, or radiation, surface roughening treatment, chemical treatment, primer treatment, etc.

[0078] The substrate to be coated can be glass, plastic, metal, ceramic, or the like.

[0079] A coating film is formed by drying the coating agent applied to the surface of a substrate. The coating agent of the present invention can form a coating film without any problems even when dried at room temperature. The temperature when drying the coating agent is preferably 5°C or higher, more preferably 20°C or higher. The temperature when drying the coating agent is preferably 300°C or lower, more preferably 200°C or lower. When heating the coating agent to dry it, the heating conditions are not particularly limited, but either a continuous or batch system may be used, and heating may be performed at normal pressure or reduced pressure. A more uniform coating film can be formed when the coating agent is left to stand at room temperature for a certain period of time before heat treatment.

[0080] The coating agent of the present invention contains Compound A, which is a combination of a siloxane oligomer or a siloxane polymer and a compound having a structure represented by formula (2), (3), (4), or (5). Therefore, the time required to form a coating film is shorter than that required for a coating agent containing a siloxane oligomer or a siloxane polymer and a compound having a structure represented by formula (2), (3), (4), or (5) in an uncombined state.

[0081] Furthermore, the coating agent of the present invention is capable of forming a coating film using a single liquid.

[0082] (Coating Film) The thickness of the coating film of the present invention is preferably 5 nm or more, more preferably 100 nm or more. If the thickness of the coating film is less than 5 nm, the hydrophilicity tends to decrease. Furthermore, the thickness of the coating film is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 2 μm or less. If the thickness of the coating film is greater than 10 μm, the adhesion to the substrate tends to decrease, and the coating film tends to peel off easily.

[0083] The coating film formed using the coating agent of the present invention has excellent hydrophilicity. The static contact angle of the coating film formed using the coating agent of the present invention with water is preferably 10° or less, more preferably 5° or less, and even more preferably 3° or less.

[0084] The coating film formed using the coating agent of the present invention contains a compound having a betaine structure. Compounds having a betaine structure have polarity, but a good balance of positive and negative charges, and have the property of being less likely to adhere to the coating film even when contacted with an ionic compound from outside the system.

[0085] For example, coating films made of inorganic polymers, such as those produced by the sol-gel method, exhibit hydrophilicity derived from silanol and are negatively charged. Furthermore, hair rinses contain cationic organic substances, such as aminosilicones and the antibacterial ingredient benzalkonium chloride. Therefore, when hair rinses adhere to a negatively charged coating film, the two are strongly bonded by ionic bonds and become fixed to the coating film. Coating films with such compounds attached lose their hydrophilicity and are no longer able to form a water film. As a result, the inherent anti-fogging and anti-fouling properties of the coating film are reduced.

[0086] On the other hand, even if a hair rinse adheres to a coating film containing a compound having a betaine structure, no strong bond is formed between the two. Therefore, the rinse can be easily removed by washing the coating film with water or a shampoo containing an organic substance. As a result, the hydrophilicity of the coating film can be maintained, and the anti-fogging and anti-fouling properties can be prevented from decreasing.

[0087] In the coating film formed using the coating agent of the present invention, the polysiloxane moiety and the betaine polymer moiety contained in Compound A do not exhibit a predetermined orientation and are thought to exist in a mixed state in the coating film.

[0088] (Uses) The use of the coating agent of the present invention is not particularly limited, but it can also be used for surface coating of mirrors and glass used in places where hair rinses may adhere, including bathrooms, changing rooms, beauty salons, barber shops, etc.

[0089] The coating agent of the present invention will be described below using examples, but the present invention is not limited to the following examples.

[0090] Example 1: 19.9 g of alcohol (manufactured by Taishin Chemical Co., Ltd., trade name: Neoethanol PIP) as a solvent, 68.5 g of ion-exchanged water, 0.2 g of nitric acid (manufactured by Kanto Chemical Co., Ltd., trade name: Nitric Acid 1.38) as a catalyst, and 1.6 g of a betaine polymer aqueous solution (manufactured by Osaka Organic Chemical Industry Ltd., trade name: LAMBIC-1000W, solids content 10 wt %, solvent: ion-exchanged water, betaine polymer: a compound having a structure represented by formula (6), a polymer having a carbobetaine structure, and alkoxysilyl groups at its terminals) were placed in a reaction vessel and stirred at room temperature for 1 hour to disperse the betaine polymer in the solution. 9.9 g of tetraethoxysilane (manufactured by Tama Chemicals Co., Ltd., trade name: TEOS, purity 95 wt %) was added thereto, and the mixture was stirred at 40°C for 15 hours to obtain a reaction solution. The solids concentration of the resulting reaction solution was 3.0% by mass. In addition, the content of betaine polymer in the solid content contained in the obtained reaction liquid was 5 mass %, and the content of silicon polymer derived from tetraethoxysilane was 95 mass %.

[0091] Next, 39.1 g of the resulting reaction solution, 35.9 g of ion-exchanged water, 25.0 g of isopropyl alcohol (manufactured by Taishin Chemical Co., Ltd., product name: IPA), and 0.04 g of an acetylene-based surfactant as a leveling agent were mixed and stirred at room temperature until the mixture was homogeneous to obtain a coating agent. The solids concentration of the resulting coating agent was 1.2 mass%. The composition of the coating agent is shown in Table 1.

[0092] The resulting coating agent was applied to the surface of a substrate by bar coating using a bar coater (bar No. 12) and then dried by heating to obtain a coating film. The substrates used were three types: a 76 mm × 52 mm glass substrate (manufactured by Matsunami Glass Industry Co., Ltd., product number: S9111, thickness: 0.8 to 1.0 mm), a 100 mm × 50 mm PET film (manufactured by Toray Industries, Inc., product number: S10, thickness: 0.05 mm), and a 50 mm × 70 mm stainless steel substrate (SUS304, mirror finish, thickness: 1.0 mm).

[0093] Two types of stainless steel substrates were used: one with an unpolished surface and one with a polished surface. The surfaces of the stainless steel substrates were polished using a glass polishing compound.

[0094] The temperature and time for heat drying were 60° C. for 10 minutes for the glass substrate, 120° C. for 2 minutes for the PET film, and 120° C. for 10 minutes for the stainless steel substrate.

[0095] <Evaluation> The coating film obtained on the substrate was tested for initial physical properties. Specifically, hydrophilicity, breath anti-fogging property, water resistance, fingerprint removability, rinse resistance, and soap resistance were evaluated as initial physical properties. Each evaluation method is as follows.

[0096] (Hydrophilicity: Water Contact Angle) The static contact angle between the surface of the coating film and a water droplet was measured using a contact angle measuring device (FAMAS, manufactured by Kyowa Interface Science Co., Ltd.) according to the θ / 2 method.

[0097] (Anti-fogging property due to breath) Breath was blown onto the surface of the coating film on the substrate, and whether or not it fogging up was visually confirmed. If the surface of the coating film did not fogging up at all, it was evaluated as ○, if it fogging up slightly, it was evaluated as △, and if it fogging up, it was evaluated as ×.

[0098] (Water resistance) The surface of the coating film on the substrate was exposed to running water (tap water shower) for about 10 seconds, and the coating film was visually inspected for any changes. If the coating film was unchanged, it was evaluated as ○, if the coating film was partially detached, it was evaluated as △, and if the coating film was completely detached, it was evaluated as ×.

[0099] (Fingerprint Removability) After a fingerprint was attached to the surface of the coating film on the substrate, running water (tap water shower) was applied for about 10 seconds, and it was visually confirmed whether the fingerprint could be removed. If the fingerprint could be removed, it was evaluated as ○, and if it could not be removed, it was evaluated as ×.

[0100] (Rinse resistance) A 1% by mass diluted solution of hair rinse (Pantene, manufactured by P&G Japan LLC) was sprayed onto the surface of the coating film on the substrate, and the center of the coating film surface was rubbed with the pad of a finger 20 times while running water (tap water shower) to perform abrasion cleaning, and then visually confirmed whether the coating film had detached. If the coating film had not detached, the static contact angle between the surface of the coating film and a water droplet was measured using a contact angle measuring device (FAMAS, manufactured by Kyowa Interface Science Co., Ltd.) using the θ / 2 method. If the static contact angle of the non-abrasion-cleaned part was 10° or less, it was evaluated as ◎; if the static contact angle of the abrasion-cleaned part was 10° or less, it was evaluated as ○; if the static contact angle of the abrasion-cleaned part was more than 10°, it was evaluated as △; and if the coating film had detached, it was evaluated as ×.

[0101] (Soap resistance) Soap bubbles were attached to the surface of the coating film on the substrate, and the center of the coating film surface was rubbed with the pad of a finger 20 times while running water (tap water shower) to perform abrasion cleaning, and then visually confirmed whether the coating film had detached or not. If the coating film had not detached, the static contact angle between the surface of the coating film and a water droplet was measured using a contact angle measuring device (FAMAS, manufactured by Kyowa Interface Science Co., Ltd.) using the θ / 2 method. If the static contact angle of the abrasion-cleaned part was 10 ° or less, it was evaluated as ○; if the static contact angle of the abrasion-cleaned part was more than 10 °, it was evaluated as △; if the coating film had detached, it was evaluated as ×.

[0102] The evaluation results of the initial physical properties of the coating film obtained in Example 1 are shown in Table 1.

[0103] In Table 1, if there was no difference in the evaluation results of the coating film between the stainless steel substrate with a polished surface and the stainless steel substrate with an unpolished surface, one result was recorded. Also, in Table 1, if there was a difference in the evaluation results of the coating film between the stainless steel substrate with a polished surface and the stainless steel substrate with an unpolished surface, the result for the stainless steel substrate with an unpolished surface was recorded to the left of the slash, and the result for the stainless steel substrate with a polished surface was recorded to the right of the slash.

[0104] Example 2 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 20.3 g, 67.1 g, 3.1 g, and 9.3 g, respectively, in the production of the reaction solution in Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The betaine polymer content of the solids contained in the resulting reaction solution was 10% by mass, and the silicon polymer content derived from tetraethoxysilane was 90% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0105] Example 3 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 21.0 g, 64.2 g, 6.2 g, and 8.3 g, respectively, in the production of the reaction solution in Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The solids content of the resulting reaction solution was 20% by mass, and the content of the silicon polymer derived from tetraethoxysilane was 80% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0106] Example 4 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 21.8 g, 61.4 g, 9.3 g, and 7.3 g, respectively, in the production of the reaction solution of Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The betaine polymer content of the solids contained in the resulting reaction solution was 30% by mass, and the silicon polymer content derived from tetraethoxysilane was 70% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0107] Example 5 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 22.5 g, 58.6 g, 12.5 g, and 6.2 g, respectively, in the production of the reaction solution in Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The solids content of the resulting reaction solution was 40% by mass, and the content of the silicon polymer derived from tetraethoxysilane was 60% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0108] Example 6 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 24.0 g, 52.9 g, 18.7 g, and 4.2 g, respectively, in the production of the reaction solution in Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The solids content of the resulting reaction solution was 60% by mass, and the silicon polymer content derived from tetraethoxysilane was 40% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0109] Example 7 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 24.7 g, 50.1 g, 21.8 g, and 3.1 g, respectively, in the production of the reaction solution in Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The betaine polymer content of the solids contained in the resulting reaction solution was 60% by mass, and the silicon polymer content derived from tetraethoxysilane was 40% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0110] Example 8 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 25.5 g, 47.3 g, 25.0 g, and 2.1 g, respectively, in the production of the reaction solution of Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The solids content of the resulting reaction solution was 80% by mass, and the content of the silicon polymer derived from tetraethoxysilane was 20% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0111] Example 9 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 25.8 g, 45.9 g, 26.5 g, and 1.6 g, respectively, in the production of the reaction solution of Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The solids content of the resulting reaction solution was 85% by mass, and the content of the silicon polymer derived from tetraethoxysilane was 15% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0112] Example 10 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, betaine polymer aqueous solution, and tetraethoxysilane were changed to 26.2 g, 44.5 g, 28.1 g, and 1.0 g, respectively, in the production of the reaction solution of Example 1, and the initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The solids content of the resulting reaction solution was 90% by mass, and the content of the silicon polymer derived from tetraethoxysilane was 10% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0113] Example 11 A coating agent was produced in the same manner as in Example 1, except that the amounts of alcohol, ion-exchanged water, and betaine polymer aqueous solution were changed to 25.0 g, 61.4 g, and 9.4 g, respectively, and 4.0 g of siloxane oligomer (manufactured by Mitsubishi Chemical Corporation, grade name: MS51, solids content 52 wt%) was added instead of tetraethoxysilane. The initial physical properties were evaluated. The solids concentration of the resulting reaction solution was 3% by mass. The betaine polymer content of the solids contained in the resulting reaction solution was 30% by mass, and the siloxane oligomer content was 70% by mass. The solids concentration of the resulting coating agent was 1.2% by mass. The composition of the coating agent is shown in Table 1, and the evaluation results are shown in Table 2.

[0114] Comparative Example 1: 24.0 g of alcohol (manufactured by Taishin Chemical Co., Ltd., product name: Neoethanol PIP) as a solvent, 67.8 g of ion-exchanged water, and 0.2 g of nitric acid (manufactured by Kanto Chemical Co., Ltd., product name: Nitric Acid 1.38) as a catalyst were placed in a reaction vessel and stirred at room temperature for 1 hour. 8.0 g of tetraethoxysilane (manufactured by Tama Chemicals Co., Ltd., product name: TEOS, purity 95 wt%) was added thereto, and the mixture was stirred at 40° C. for 15 hours to obtain a reaction solution.

[0115] Next, 35.5 g of the resulting reaction solution, 35.8 g of ion-exchanged water, 25.0 g of isopropyl alcohol (manufactured by Taishin Chemical Co., Ltd., trade name: IPA), 0.04 g of an acetylene surfactant as a leveling agent, and 3.7 g of an aqueous betaine polymer solution (manufactured by Osaka Organic Chemical Industry Ltd., trade name: LAMBIC-1000W, solids content 10 wt%, solvent: ion-exchanged water) were mixed and stirred at room temperature until the entire mixture was uniform, yielding a coating agent. The content of betaine polymer in the solids content of the resulting coating agent was 30% by mass, and the content of silicon polymer derived from tetraethoxysilane was 70% by mass. The composition of the coating agent is shown in Table 1.

[0116] Using the obtained coating agent, a coating film was produced and its initial physical properties were evaluated in the same manner as in Example 1. The evaluation results are shown in Table 2.

[0117] Comparative Example 2 The same substrate as in Example 1 was evaluated for initial physical properties without applying a coating agent. The evaluation results are shown in Table 2. In addition, when no evaluation was performed, "-" is written next to the evaluation results.

[0118]

[0119]

[0120] From the above results, it is clear that the present invention can provide a coating film that is excellent in at least one of hydrophilicity, breath anti-fogging property, water resistance, fingerprint removability, rinse resistance, and soap resistance.

Claims

1. In the molecule, the formula (1): (R １ is an organic group or a group having a Si—O bond, and R ２ is an organic group or a group having a Si—O bond, and R １ and R ２ may be the same or different, n is an integer of 2 or more, and a plurality of R １ may be the same or different, and multiple R ２ may be the same or different) and a betaine structure.

2. The coating agent according to claim 1, wherein the betaine structure is a carbobetaine structure, a sulfobetaine structure, or a phosphobetaine structure.

3. The compound has the formula (2): , formula (3): , formula (4): Or formula (5): (R ３ is hydrogen or a methyl group, R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ 3. The coating agent according to claim 1 or 2, comprising a structure represented by the formula: (aromatic ring, phenylene group).

4. The coating agent according to claim 1 or 2, wherein the structure represented by formula (1) is obtainable by hydrolysis of a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent, followed by a condensation reaction.

5. The coating agent according to claim 1 or 2, wherein the mass ratio of the structure represented by formula (1) to the compound ((mass of the structure represented by formula (1)) / (mass of the compound)) is 1 / 100 to 99.9 / 100.

6. The coating agent according to claim 3, wherein the mass ratio of the structure represented by formula (2), (3), (4), or (5) to the compound ((mass of the structure represented by formula (2), (3), (4), or (5)) / (mass of the compound)) is 0.1 / 100 to 99 / 100.

7. A coating film obtained by applying the coating agent according to claim 1 or 2 to an object and drying it.

8. An article having a coating film formed by applying the coating agent according to claim 1 or 2 to an object and drying it.

9. A method for applying the coating agent according to claim 1 or 2 to an object.

10. A step of hydrolyzing a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent and subjecting it to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer; and reacting the obtained siloxane oligomer or siloxane polymer with a compound represented by formula (2): , formula (3): , formula (4): Or formula (5): (R ３ is hydrogen or a methyl group, R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)) and having a silanol group and / or a group capable of reacting with and bonding to a functional group derived from a silane coupling agent contained in a siloxane oligomer or a siloxane polymer.

11. A dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or a silane coupling agent and a compound represented by the formula (2): , formula (3): , formula (4): Or formula (5): (R ３ is hydrogen or a methyl group, R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)) and having a silanol group and / or a group capable of reacting with and bonding to a functional group possessed by the silane coupling agent.

12. The method according to claim 10 or 11, further comprising a step of applying a coating agent containing the compound obtained by the reacting step to an object.

13. A step of hydrolyzing a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent and subjecting it to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer; and reacting the obtained siloxane oligomer or siloxane polymer with a compound represented by formula (2): , formula (3): , formula (4): Or formula (5): (R ３ is hydrogen or a methyl group, R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)) and having a group capable of reacting and bonding with a silanol group and / or a functional group derived from a silane coupling agent contained in a siloxane oligomer or a siloxane polymer.

14. A dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or a silane coupling agent and a compound represented by the formula (2): , formula (3): , formula (4): Or formula (5): (R ３ is hydrogen or a methyl group, R ４ is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R ３ may be the same or different, and multiple R ４ may be the same or different, and multiple R ４ At least one of the groups is a group having a betaine structure, and Ar is C ６ H ４ (aromatic ring, phenylene group)) and having a silanol group and / or a group that can react with and bond to a functional group possessed by the silane coupling agent.

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