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

Abstract

To provide a coating agent that is able to yield a novel coating film.SOLUTION: 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 or different from each other, n is an integer of 2 or greater, multiple R1 moieties may be the same or different from each other, and multiple R2 moieties may be the same or different from each other.)SELECTED DRAWING: None

Description

Technical Field

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

Background Art

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

[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 the adhesion to a substrate by forming a glass-like coat layer made of tetraalkoxysilane and a betaine structure layer. The coating film can be obtained by applying a glass-like coat agent to the surface of a substrate and curing it, and then applying a betaine structure agent to the surface of the glass-like coat layer and curing it (two-component composition). Alternatively, the coating film can be obtained by mixing a glass-like coat agent and a betaine structure agent, applying the mixture to the surface of a substrate, and then waiting for it to naturally separate into two layers and cure (one-component composition). Further, Patent Document 1 describes that the betaine structure part is oriented on the surface of the betaine structure layer, polarized into a positive charge on the nitrogen atom and a negative charge on the oxygen atom, exhibits hydrophilicity, and exhibits antifouling properties.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

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

Means for Solving the Problems

[0006] The object of the present invention is [1] A compound having, in the molecule, a structure represented by the formula (1):

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[10] A step of hydrolyzing and subjecting a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer, and the obtained siloxane oligomer or siloxane polymer, and formula (2):

Chemical formula

[11] A dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent, and formula (2): [Chemical formula] and formula (3): [Chemical formula] and formula (4): [Chemical formula] or formula (5): [Chemical formula] (R 3 is a hydrogen or methyl group, R 4is hydrogen or an organic group, m is an integer of 2 or more, and a plurality of R 3 's may each be the same or different, and a plurality of R 4 's may each be the same or different, and a plurality of R 4 at least one of which is a group having a betaine structure, and Ar is C 6 H 4 (an aromatic ring, a phenylene group)), and reacting with a compound having a group capable of reacting and bonding with a silanol group and / or a functional group of a silane coupling agent;

[12] A method according to

[10] or

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

[13] Hydrolyzing and subjecting a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer, and the obtained siloxane oligomer or siloxane polymer and formula (2): [Chemical formula] , formula (3): [Chemical formula] , formula (4): [Chemical formula] , or formula (5): [Chemical formula] (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 's may each be the same or different, and a plurality of R 4 's may each be the same or different, and a plurality of R 4At least one of them is a group having a betaine structure, and Ar is C 6 H 4 (an aromatic ring, a phenylene group)), and reacting with a compound 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, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent and formula (2):

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Advantages of the Invention

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

Embodiment for Carrying Out the Invention

[0008] Hereinafter, each component of the coating agent of the present invention, the production method, the method for forming the coating film, etc. will be described.

[0009] The coating agent of the present invention has, in the molecule, the formula (1):

Chemical formula

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

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

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

[0013] R in formula (1) 1 or R 2 The alkyl group employed for R or R may be linear, may have a branched structure, and may have an unsaturated bond. Also, a part of the hydrogen atoms in the alkyl group may be substituted with other atoms or substituents other than hydrogen atoms.

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

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

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

[0017] R 1 or R 2 may be a group having an Si—O bond. That is, in the structure represented by the formula (1), the Si—O bonds may be continuously linear, or the chain in which the Si—O bonds are continuous may have branches. Further, the structure represented by the formula (1) may have a three-dimensional network structure.

[0018] In the formula (1), n is an integer of 2 or more. In the formula (1), n is preferably 2 or more, more preferably 3 or more, and still more preferably 5 or more. In the formula (1), n is preferably 5000 or less, more preferably 3000 or less, and still more preferably 2000 or less.

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

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

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

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

[0023] When hydrolyzing and subjecting dialkoxydialkylsilane, dialkoxydialkylsilane, trialkoxyalkylsilane, tetraalkoxysilane, and / or a silane coupling agent to a condensation reaction, a catalyst may be used. By using a catalyst, the hydrolysis reaction and the condensation reaction can be promoted. The catalyst used is not particularly limited. For example, mineral acids such as hydrochloric acid, nitric acid, sulfuric acid, and phosphoric acid, or organic acids such as formic acid and acetic acid may be used as the catalyst. The amount of the catalyst used can also be appropriately designed.

[0024] The "betaine structure" refers to a structure in which an atom that can be positively charged and an atom that can be negatively charged are present at non-adjacent positions within the same molecule (or the same structure), the atom that can be positively charged does not have a dissociable hydrogen atom bonded thereto, and the entire molecule (or the entire structure) does not have a charge.

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

[0026] In the carboxybetaine structure, the carboxy group has a negative charge. In the sulfobetaine structure, the sulfo group has a negative charge. In the phosphobetaine structure, the phosphate group has a negative charge.

[0027] In addition, 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] In addition, Compound A has the formula (2):

Chemical formula

Chemical formula

Chemical formula

Chemical formula

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

[0030] Also, the organic group employed for R in formula (2), (3), (4) or (5) 4 contains a group having a betaine structure. Regarding the betaine structure contained in the organic group employed for R in formula (2), (3), (4) or (5), the description about the above betaine structure can be adopted within the necessary range. The organic group employed for R in formula (2), (3), (4) or (5) 4 Regarding the betaine structure contained in the organic group employed for R in formula (2), (3), (4) or (5), the description about the above betaine structure can be adopted within the necessary range. The organic group employed for R in formula (2), (3), (4) or (5) 4The betaine structure adopted 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 50000 or less, more preferably 20000 or less, and even more preferably 10000 or less.

[0032] The structure represented by formula (2) is, for example, formula (6):

Chemical formula

[0033] Formula (6) represents a structure in which a (meth)acrylate unit having a group with a betaine structure and a (meth)acrylate unit having an arbitrary organic group are block copolymerized. For example, a (meth)acrylate unit having a group with a betaine structure and a (meth)acrylate unit having an arbitrary organic group may be randomly copolymerized, alternately copolymerized, or graft copolymerized.

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

[0035] R in formula (6) 5 The carbon number of the alkyl group employed in is preferably 1 or more. Also, R in formula (6) 5 The carbon number of the alkyl group employed in 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. Also, 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 the structure represented by formula (1) with a compound having the structure represented by formula (2), (3), (4), or (5), the mass ratio of the structure represented by formula (1) to compound A can be obtained 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. Also, 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. Also, 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. Also, 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. Also, 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. Also, 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 obtained by copolymerizing monomers capable of forming the structure represented by formula (2), (3), (4), or (5) in any combination, and the structure represented by formula (1).

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

[0044] Compound B has a group that can react with and bond to a silanol group. Compound B preferably has, for example, a group that can react with and bond to a silanol group at the terminal of a compound having a structure represented by formula (2), (3), (4), or (5). The group that can react with and bond 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 the generated silanol group reacts with the group that can react with and bond to the silanol group of Compound B (for example, an alkoxysilyl group) and is bonded by dehydration condensation to obtain Compound A.

[0045] Also, Compound A can be obtained by hydrolyzing and subjecting to a condensation reaction a silane coupling agent, a dialkoxydialkylsilane, a trialkoxyalkylsilane, and / or a tetraalkoxysilane to obtain a siloxane oligomer or a siloxane polymer, 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 that can react with and bond to a functional group derived from the silane coupling agent contained in the siloxane oligomer or the siloxane polymer. Hereinafter, a compound having a structure represented by formula (2), (3), (4), or (5) and having a group that can react with and bond to a 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 that can react and bond with a functional group derived from a silane coupling agent, which is contained in a siloxane oligomer or a siloxane polymer. The functional group derived from the silane coupling agent is not particularly limited, and 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 that can react and bond with the functional group derived from the silane coupling agent is not particularly limited as long as it can react with functional groups such as an epoxy group, an amino group, an isocyanate group, a mercapto group, a carboxyl group, a vinyl group, and a (meth)acrylic group.

[0047] Also, Compound A can be obtained by reacting a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent with a compound having a structure represented by formula (2), (3), (4), or (5) and having a group that can react and bond with a silanol group. Further, Compound A can 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 that can react and bond with a silanol group, or by reacting a silane coupling agent with a dialkoxydialkylsilane, a trialkoxyalkylsilane, and / or a tetraalkoxysilane and a compound having a structure represented by formula (2), (3), (4), or (5) and having a group that can react and bond with a silanol group. Compound A obtained by reacting these silane coupling agents has a structure represented by formula (2), (3), (4), or (5) and a group that can react and bond with a silanol group, and the structure represented by formula (1) are bonded by dehydration condensation of the silanol group, so that functional groups other than the alkoxysilyl group derived from the silane coupling agent remain without reacting.

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

[0049] Also, 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 groups of the compound having a structure represented by Formula (2), (3), (4), or (5) can include 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, etc., which can react and bond with the epoxy group (glycidyl group).

[0050] Also, 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 groups of the compound having a structure represented by Formula (2), (3), (4), or (5) can include a halogen atom (chlorine atom), maleimide, an epoxy group, carbodiimide, a carboxylic acid, a carboxylic acid ester, an isocyanate group, etc. When the amino group reacts with the halogen atom, the halogen atom is eliminated to obtain Compound A. When the amino group reacts with the carboxylic acid, water is eliminated to obtain Compound A. When the amino group reacts with the carboxylic acid ester, alcohol is eliminated to obtain Compound A.

[0051] Also, 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 groups possessed by the compound having the structure represented by formula (2), (3), (4) or (5) may include a vinyl group, a hydroxyl group, a silyl group, etc.

[0052] Also, 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 groups possessed by the compound having the structure represented by formula (2), (3), (4) or (5) may include a (meth)acrylic group, a styryl group, etc.

[0053] Also, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is an isocyanate group, the functional groups possessed by the compound having the structure represented by formula (2), (3), (4) or (5) may include a hydroxyl group, a carboxyl group, etc.

[0054] Also, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a mercapto group, the functional groups possessed by the compound having the structure represented by formula (2), (3), (4) or (5) may include an isocyanate group, a mercapto group, a vinyl group, etc. When the mercapto groups react with each other, hydrogen is eliminated to obtain compound A.

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

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

[0057] Further, for example, when the functional group derived from the silane coupling agent contained in the siloxane oligomer or siloxane polymer is a carbonyl group, as the functional group of the compound having the structure represented by formula (2), (3), (4) or (5), a hydrazide group, an amino group, etc. can be adopted. When the carbonyl group and the hydrazide group react, water is eliminated to obtain compound A. Also, when the carbonyl group and the amino group react, water is eliminated to obtain compound A.

[0058] Further, for example, when the functional group of the compound having the structure represented by formula (2), (3), (4) or (5) is an epoxy group (glycidyl group), as the functional group of the silane coupling agent, 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, etc. can be adopted.

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

[0060] Further, for example, when the functional group of the compound having the structure represented by formula (2), (3), (4) or (5) is a vinyl group, the functional groups of the silane coupling agent can include vinyl group, hydroxyl group, silyl group, etc.

[0061] Further, for example, when the functional group of the compound having the structure represented by formula (2), (3), (4) or (5) is a (meth)acrylic group, the functional groups of the silane coupling agent can include (meth)acrylic group, styryl group, etc.

[0062] Further, for example, when the functional group of the compound having the structure represented by formula (2), (3), (4) or (5) is an isocyanate group, the functional groups of the silane coupling agent can include hydroxyl group, carboxyl group, etc.

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

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

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

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

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

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

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

[0070] Compound A contains an organic group and an inorganic group and has a complex structure. Therefore, it is not practical and difficult to specify the structure, properties, etc. of the compound.

[0071] (Solvent) The coating agent of the present invention contains a solvent. As the solvent, water, an alcohol solvent containing water, or glycol ether can be used. Examples of the alcohol solvent include lower aliphatic alcohol solvents such as 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, n-octanol, 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 the glycol ether include ethylene glycol monobutyl ether and its derivatives, propylene glycol monoalkyl ether, petylene glycol monoalkyl ether, diethylene glycol monobutyl ether, and their derivatives. These alcohol solvents and glycol ethers can be used alone or in combination. By using these water or alcohol solvents containing water, or glycol ether, the compound can be stably dispersed.

[0072] In the coating agent of the present invention, it is preferable to adjust the amount of the solvent so that the solid content concentration 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. When the solid content concentration is less than 0.1% by mass, a large amount of the coating agent is required to form a coating film with a desired thickness, so the work efficiency tends to deteriorate. It is preferable to adjust the amount of the solvent so that the solid content concentration is 30% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less. When the solid content concentration exceeds 30% by mass, the storage stability of the coating agent tends to decrease.

[0073] (Other additives) In the coating agent of the present invention, surfactants such as leveling agents for the purpose of smoothing the coating film, thickeners for the purpose of preventing repellency, and coloring pigments etc. according to the application can be added. Other additives can 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] (Manufacturing method of 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 the 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 to disperse Compound A and the additive in the solvent.

[0075] (Method for forming coating film) As a method for forming a coating film on a substrate using the coating agent of the present invention, there are a method of applying the coating agent to the surface of the substrate and a method of immersing the substrate in the coating agent. The method of applying the coating agent to the surface of the substrate is particularly preferable because it is simple, low in cost, and the required film thickness can be easily controlled.

[0076] The coating method is not particularly limited, and known techniques may be employed. For example, coating means such as spin coating, dipping, spraying, flow coating, bar coating, roller coating, reverse coating, flexo printing, printing, etc. can be appropriately adopted.

[0077] Also, in order to improve the adhesion between the substrate and the coating film, the surface of the substrate may be pretreated. Examples of the pretreatment method include corona discharge treatment, glow discharge treatment, treatment with ionizing active rays such as ultraviolet rays, electron beams or radiation, roughening treatment, chemical treatment or primer treatment.

[0078] As the substrate, glass, plastic, metal, ceramics, etc. can be the object of coating.

[0079] A coating film is formed by drying the coating agent applied to the surface of the substrate. The coating agent of the present invention can form a coating film without problems even when dried at room temperature. The temperature during drying the coating agent is preferably 5°C or higher, more preferably 20°C or higher. Also, the temperature during drying the coating agent is preferably 300°C or lower, more preferably 200°C or lower. When heating during drying the coating agent, the heating conditions are not particularly limited, and it can be continuous or batch type, and it can also be heated at normal pressure or reduced pressure. When standing at room temperature for a certain period of time before the heat treatment, it is possible to form a more uniform coating film.

[0080] The coating agent of the present invention contains Compound A in a state where a siloxane oligomer or siloxane polymer is bonded to a compound having a structure represented by formula (2), (3), (4) or (5). Therefore, the time required until the formation of the coating film is shorter than that of a coating agent containing a siloxane oligomer or siloxane polymer and a compound having a structure represented by formula (2), (3), (4) or (5) without bonding them.

[0081] Moreover, the coating agent of the present invention can form a coating film with a single component.

[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. When the thickness of the coating film is less than 5 nm, the hydrophilicity tends to decrease. Also, 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. When the thickness of the coating film exceeds 10 μm, the adhesion to the substrate decreases, and it tends to peel off easily.

[0083] The coating film formed using the coating agent of the present invention is excellent in hydrophilicity. The static contact angle of the coating film formed using the coating agent of the present invention with respect to 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. Although a compound having a betaine structure has polarity, the positive and negative charges are balanced, and it has the property of being difficult to adhere even when an ionic compound contacts from outside the system.

[0085] For example, a coating film made of an inorganic polymer such as the sol-gel method exhibits hydrophilicity derived from silanol and has a negative charge. Also, hair rinses contain cationic organic substances such as aminosilicone and benzalkonium chloride which is a bactericidal component. Therefore, when a hair rinse adheres to a negatively charged coating film, the two are strongly bonded by an ionic bond and adhere to the coating film. A coating film to which such a compound adheres loses its hydrophilicity and cannot form a water film. As a result, there arises a problem that the original anti-fogging and anti-fouling properties of the coating film deteriorate.

[0086] Even when a hair conditioner adheres to a coating film containing a compound having a betaine structure, a strong bond does not form between the two. Therefore, the conditioner 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, preventing a decrease in anti-fogging and anti-fouling properties.

[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 considered to be present in a mixed state in the coating film.

[0088] (Use) The use of the coating agent of the present invention is not particularly limited, and it can also be used for applications such as surface coating of mirrors and glass used in places where hair conditioner may adhere. Places where hair conditioner may adhere include bathrooms, dressing rooms, beauty salons, barbershops, etc.

Examples

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

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

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

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

[0093] As the stainless steel substrates, two types were used: those with an unpolished surface and those with a polished surface. The polishing of the surface of the stainless steel substrates was performed using a compound for glass polishing.

[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> Regarding the coating film obtained on the substrate, tests of initial physical properties were conducted. Specifically, hydrophilicity, anti-fogging property against exhaled breath, water resistance, fingerprint removability, rinsing resistance, and soap resistance were evaluated as the initial physical properties. Each evaluation method is as described below.

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

[0097] (Anti-fogging property against exhaled breath) Exhaled breath was blown onto the surface of the coating film on the substrate, and whether it fogged or not was visually confirmed. When the surface of the coating film did not fog at all, it was evaluated as ○; when it fogged slightly, it was evaluated as △; when it fogged, it was evaluated as ×.

[0098] (Water resistance) Running water (shower of tap water) was applied to the surface of the coating film on the substrate for about 10 seconds, and whether there was any change in the coating film was visually confirmed. When there was no change in the coating film, it was evaluated as ○; when a part peeled off, it was evaluated as △; when it peeled off completely, it was evaluated as ×.

[0099] (Fingerprint removability) After fingerprints were attached to the surface of the coating film on the substrate, running water (shower of tap water) was applied for about 10 seconds, and whether the fingerprints could be removed was visually confirmed. When the fingerprints could be removed, it was evaluated as ○; when they could not be removed, it was evaluated as ×.

[0100] (Rinse resistance) A 1% by mass dilution of hair rinse (manufactured by P&G Japan K.K., product name: Pantene) was sprayed onto the surface of the coating film on the substrate, and the central portion of the coating film surface was rubbed 20 times back and forth with the pad of a finger while running water (tap water shower) was applied, followed by abrasion cleaning. Then, it was visually confirmed whether or not the coating film had peeled off. When the coating film had not peeled off, the static contact angle between the surface of the coating film and a water droplet was measured using the θ / 2 method with a contact angle measuring device (FAMAS, manufactured by Kyowa Interface Science Co., Ltd.). When the static contact angle of the non-abraded and cleaned portion was 10° or less, it was evaluated as ◎; when the static contact angle of the abraded and cleaned portion was 10° or less, it was evaluated as ○; when the static contact angle of the abraded and cleaned portion was greater than 10°, it was evaluated as △; and when the coating film had peeled off, it was evaluated as ×.

[0101] (Soap resistance) Foam made with soap was attached to the surface of the coating film on the substrate, and the central portion of the coating film surface was rubbed 20 times back and forth with the pad of a finger while running water (tap water shower) was applied, followed by abrasion cleaning. Then, it was visually confirmed whether or not the coating film had peeled off. When the coating film had not peeled off, the static contact angle between the surface of the coating film and a water droplet was measured using the θ / 2 method with a contact angle measuring device (FAMAS, manufactured by Kyowa Interface Science Co., Ltd.). When the static contact angle of the abraded and cleaned portion was 10° or less, it was evaluated as ○; when the static contact angle of the abraded and cleaned portion was greater than 10°, it was evaluated as △; and when the coating film had peeled off, it was evaluated as ×.

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

[0103] In Table 1, when there was no difference in the evaluation results of the coating film between the polished stainless-steel substrate and the unpolished stainless-steel substrate, one result was described. Also, in Table 1, when there was a difference in the evaluation results of the coating film between the polished stainless-steel substrate and the unpolished stainless-steel substrate, the result of the unpolished stainless-steel substrate was described on the left side of the slash, and the result of the polished stainless-steel substrate was described on the right side of the slash.

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

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

[0106] (Example 4) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1 except that the alcohol was changed to 21.8 g, the ion-exchanged water was changed to 61.4 g, the betaine polymer aqueous solution was changed to 9.3 g, and the tetraethoxysilane was changed to 7.3 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Further, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 30% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 70% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1 except that the alcohol was changed to 22.5 g, the ion-exchanged water was changed to 58.6 g, the betaine polymer aqueous solution was changed to 12.5 g, and the tetraethoxysilane was changed to 6.2 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Further, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 40% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 60% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1 except that the alcohol was changed to 24.0 g, the ion-exchanged water was changed to 52.9 g, the betaine polymer aqueous solution was changed to 18.7 g, and the tetraethoxysilane was changed to 4.2 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Further, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 60% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 40% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1, except that the alcohol was changed to 24.7 g, the ion-exchanged water was changed to 50.1 g, the betaine polymer aqueous solution was changed to 21.8 g, and the tetraethoxysilane was changed to 3.1 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Also, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 60% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 40% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1, except that the alcohol was changed to 25.5 g, the ion-exchanged water was changed to 47.3 g, the betaine polymer aqueous solution was changed to 25.0 g, and the tetraethoxysilane was changed to 2.1 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Also, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 80% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 20% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1, except that the alcohol was changed to 25.8 g, the ion-exchanged water was changed to 45.9 g, the betaine polymer aqueous solution was changed to 26.5 g, and the tetraethoxysilane was changed to 1.6 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Also, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 85% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 15% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, a coating agent was produced in the same manner as in Example 1 except that the alcohol was changed to 26.2 g, the ion-exchanged water was changed to 44.5 g, the betaine polymer aqueous solution was changed to 28.1 g, and the tetraethoxysilane was changed to 1.0 g, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Further, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 90% by mass, and the content of the silicon polymer derived from tetraethoxysilane is 10% by mass. Further, the solid content concentration of the obtained coating agent is 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) In the production of the reaction solution of Example 1, the alcohol was changed to 25.0 g, the ion-exchanged water was changed to 61.4 g, the betaine polymer aqueous solution was changed to 9.4 g, and 4.0 g of a siloxane oligomer (manufactured by Mitsubishi Chemical Corporation, grade name: MS51, solid content 52 wt%) was added instead of tetraethoxysilane. A coating agent was produced in the same manner as in Example 1, and the initial physical properties were evaluated. The solid content concentration of the obtained reaction solution is 3% by mass. Further, in the solid content contained in the obtained reaction solution, the content of the betaine polymer is 30% by mass, and the content of the siloxane oligomer is 70% by mass. Further, the solid content concentration of the obtained coating agent is 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 Daishin Chemical Co., Ltd., trade name: Neoethanol PIP) and 67.8 g of ion-exchanged water as solvents and 0.2 g of nitric acid (manufactured by Kanto Chemical Co., Inc., trade name: Nitric Acid 1.38) as a catalyst were placed in a reaction vessel and stirred at room temperature for 1 hour. Thereto, 8.0 g of tetraethoxysilane (manufactured by Tama Chemical Industry Co., Ltd., trade name: TEOS, purity 95 wt%) was added, and the mixture was stirred at 40 ° C for 15 hours to obtain a reaction solution.

[0115] Next, 35.5 g of the obtained reaction solution, 35.8 g of ion-exchanged water, 25.0 g of isopropyl alcohol (manufactured by Daishin Chemical Co., Ltd., trade name: IPA), 0.04 g of an acetylene-based surfactant as a leveling agent, and 3.7 g of a betaine polymer aqueous solution (manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name: LAMBIC-1000W, solid content 10 wt%, solvent: ion-exchanged water) were mixed and stirred at room temperature until the whole became uniform to obtain a coating agent. The content of the betaine polymer in the solid content contained in the obtained coating agent was 30% by mass, and the content of the 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 in the same manner as in Example 1, and the initial physical properties were evaluated. The evaluation results are shown in Table 2.

[0117] (Comparative Example 2) For the same substrate as in Example 1, the initial physical properties were evaluated without applying the coating agent. The evaluation results are shown in Table 2. In the case where the evaluation was not performed, it was described as ― in the evaluation results.

[0118]

Table 1

[0119]

Table 2

[0120] From the above results, it can be seen that according to the present invention, a coating film excellent in at least one of hydrophilicity, anti-fogging property against exhaled breath, water resistance, fingerprint removability, rinsing resistance, and soap resistance can be obtained.

Claims

1. In the molecule, formula (1): 【Chemical Formula 1】 (R １ is an organic group or a group having an Si—O bond, R ２ is an organic group or a group having an Si—O bond, R １ and R ２ may be the same or different, n is an integer of 2 or more, and each of the plurality of R １ may be the same or different, and each of the plurality of R ２ may be the same or different), and a compound having 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 is represented by formula (2): [Chemical 2] , formula (3): [Chemical Formula 3] , formula (4): 【Chemical Formula 4】 , or formula (5): 【Chemical 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 each of the plurality of R ３ may be the same or different, and each of the plurality of R ４ may be the same or different, and at least one of the plurality of R ４ is a group having a betaine structure, and Ar is C ６ H ４ (an aromatic ring, a phenylene group)), and the coating agent according to claim 1 or 2, which contains a structure represented by

4. The coating agent according to claim 1 or 2, wherein the structure represented by formula (1) can be obtained by hydrolyzing and subjecting a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent to 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 to be coated and drying it.

8. An article provided with a coating film obtained by applying the coating agent according to claim 1 or 2 to an object to be coated and drying it.

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

10. A step of hydrolyzing and subjecting a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer, The obtained siloxane oligomer or siloxane polymer and formula (2): [[Chemical Formula 6]] , formula (3): [Chemical Formula 7] , formula (4): 【Chemical Formula 8】 , or formula (5): 【Chemical Formula 9】 (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 each of the plurality of R ３ may be the same or different, and each of the plurality of R ４ may be the same or different, and at least one of the plurality of R ４ is a group having a betaine structure, and Ar is C ６ H ４ (an aromatic ring, a phenylene group)), and reacting with a compound 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).

11. A dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent and formula (2): 【Chemical 10】 , formula (3): 【Chemical 11】 , formula (4): 【Chemical Formula 12】 , or formula (5): 【Chemical 13】 (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 each of the plurality of R ３ may be the same or different, and each of the plurality of R ４ may be the same or different, and at least one of the plurality of R ４ is a group having a betaine structure, and Ar is C ６ H ４ (an aromatic ring, a phenylene group)), and reacting with a compound having a group capable of reacting and bonding with a silanol group and / or a functional group of a silane coupling agent).

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

13. Hydrolyzing and subjecting a dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent to a condensation reaction to obtain a siloxane oligomer or a siloxane polymer; The obtained siloxane oligomer or siloxane polymer and formula (2): 【Chemical Formula 14】 Formula (3): 【Chemical Formula 15】 Formula (4): 【Chemical 16】 Or formula (5): 【Chemical 17】 (R ３ is a hydrogen or methyl group, R ４ is a hydrogen or organic group, m is an integer of 2 or more, and each of the plurality of R ３ may be the same or different, and each of the plurality of R ４ may be the same or different, and at least one of the plurality of R ４ is a group having a betaine structure, Ar is C ６ H ４ (an aromatic ring, a phenylene group)), and reacting with a compound 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 siloxane polymer. A method for producing a coating agent.

14. A dialkoxydialkylsilane, a trialkoxyalkylsilane, a tetraalkoxysilane, and / or a silane coupling agent and formula (2): 【Chemical 18】 Formula (3): 【Chemical Formula 19】 Formula (4): 【Chemical 20】 Or formula (5): 【Chemical 21】 (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 each of the plurality of R ３ may be the same or different, and each of the plurality of R ４ may be the same or different, and at least one of the plurality of R ４ is a group having a betaine structure, and Ar is C ６ H ４ (an aromatic ring, a phenylene group)), and reacting with a compound having a group capable of reacting and bonding with a silanol group and / or a functional group of a silane coupling agent. A method for producing a coating agent having a step.

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