Aqueous solution containing polysiloxane compound having 1,2-diol structure and polysiloxane compound having amino acid structure, and method for producing the same

Abstract

To provide an aqueous solution containing a polysiloxane compound that does not form a gel and can be maintained in a uniform state even in a basic aqueous solution.SOLUTION: An aqueous solution contains: a polysiloxane compound having a 1,2-diol structure represented by the following general formula (1) or (2); and a polysiloxane compound having an amino acid structure represented by the following general formula (3).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an aqueous solution containing a polysiloxane compound having a 1,2-diol structure and a polysiloxane compound having an amino acid structure, and a method for producing the same. [Background technology]

[0002] Organosilicon compounds containing hydrolyzable silyl groups and organic groups produce silanol groups through hydrolysis of the hydrolyzable silyl groups, which form covalent bonds with hydroxyl groups on the surface of inorganic materials. Furthermore, the organic groups react with the organic materials, enabling them to bond together, which would normally be difficult to do. This provides organic-inorganic composite materials with properties such as improved heat resistance, water resistance, weather resistance, and mechanical strength, as well as adhesion, dispersibility, hydrophobicity, and rust resistance. Taking advantage of these properties, the organosilicon compounds are used in a wide range of fields and applications, such as silane coupling agents, resin additives, surface treatment agents, fiber treatment agents, adhesives, paint additives, and polymer modifiers.

[0003] Among the above organosilicon compounds, organosilicon compounds having an epoxy group, such as γ-glycidoxypropyltrimethoxysilane, have been widely used as surface treatment agents for copper foils and inorganic fillers in printed circuits, and as adhesion aids for compositions. For example, Patent Document 1 reports that a silane coupling agent obtained by hydrolyzing a silane compound having an epoxy group can be used as a surface treatment agent for copper foil to improve the adhesion between copper foil and resin. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 8-295736 Summary of the Invention [Problem to be solved by the invention]

[0005] In the surface treatment of such inorganic materials, an aqueous solution in which the desired organosilicon compound is dissolved in water is generally used. However, although aqueous solutions containing silane compounds having epoxy groups are highly stable under acidic and neutral conditions and have a uniform composition, they are unstable under basic conditions and will form a gel when the aqueous solution becomes basic due to the addition of other components. If a gel forms in the aqueous solution, when the aqueous solution is applied to a substrate as a surface treatment agent, a non-uniform film will be formed, which may adversely affect performance.

[0006] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an aqueous solution containing a polysiloxane compound that does not form a gel even in a basic aqueous solution and can maintain a homogeneous state. [Means for solving the problem]

[0007] As a result of extensive research into achieving the above object, the present inventors discovered that an aqueous solution containing a polysiloxane compound having a 1,2-diol structure and a polysiloxane compound having an amino acid structure does not form a gel and remains homogeneous even when made basic by the addition of other components, thereby completing the present invention.

[0008] Therefore, the present invention provides 1. An aqueous solution containing a polysiloxane compound having a 1,2-diol structure represented by the following general formula (1) or (2) and a polysiloxane compound having an amino acid structure represented by the following general formula (3): [ka] (In the formula, R 1 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom, and R 2 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, m is 0 or a positive number less than 3, n is 0 or 1, and n+m is 0 or a positive number less than 3. [ka] (In the formula, R 1 , R 2 , m and n have the same meanings as above. [ka] (In the formula, R 2 , m and n have the same meanings as above, R 3 , R 4 and R 5 each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and a is 0 or 1. 2. An aqueous solution of 1 containing 1 to 10,000 parts by mass of the polysiloxane compound having an amino acid structure per 100 parts by mass of the polysiloxane compound having a 1,2-diol structure; 3. The aqueous solution of 1, in which the total mass of the polysiloxane compound having a 1,2-diol structure and the polysiloxane compound having an amino acid structure is 0.01 to 100 parts by mass per 100 parts by mass of water; 4. A method for producing the aqueous solution according to 1 or 2, which comprises mixing a silane compound having an epoxy structure represented by the following general formula (4) or (5), a silane compound having an amino acid ester structure represented by the following general formula (6), and water: [ka] (In the formula, R 1 , R 2 and n have the same meaning as above, R 6 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. [ka] (In the formula, R 1 , R 2 , R 6 and n have the same meaning as above. [ka] [(wherein, R 2 ~R 6, a and n have the same meanings as above, R 7 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms or a group represented by the following general formula (7): -SiR 8 R 9 R 10 (7) (In the formula, R 8 , R 9 and R 10 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. represents a triorganosilyl group represented by the following formula: to provide. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide an aqueous solution containing a polysiloxane that has high storage stability regardless of the pH of the aqueous solution and does not form gels. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will be specifically described below. The polysiloxane compound having a 1,2-diol structure contained in the aqueous solution of the present invention is represented by the following general formula (1) (hereinafter referred to as "compound (1)") or (2) (hereinafter referred to as "compound (2)"):

[0011] [ka]

[0012] In the above general formula (1) or (2), R 1 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms, which may contain an oxygen atom.

[0013] R 1 Examples of the divalent hydrocarbon group include linear, branched, or cyclic alkylene groups, alkenylene groups, arylene groups, and aralkylene groups. Specific examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, hexamethylene, octamethylene, and decylene; branched alkylene groups such as methyltrimethylene and methyltetramethylene; cyclic alkylene groups such as cyclohexylene and methylenecyclohexylenemethylene; linear alkenylene groups such as vinylene, propenylene, butenylene, hexenylene, and octenylene; branched alkenylene groups such as methylvinylene and isobutenylene; arylene groups such as phenylene; and aralkylene groups such as methylenephenylene and methylenephenylenemethylene. Among these, a linear alkylene group is preferred from the viewpoint of ease of procurement of raw materials.

[0014] Some or all of the hydrogen atoms in each of the hydrocarbon groups may be substituted with other substituents, and specific examples of these substituents include alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, (iso)propoxy, and phenoxy; halogen atoms such as fluorine, chlorine, bromine, and iodine; cyano, amino, acyl, alkoxycarbonyl groups having 1 to 5 carbon atoms, carboxy, alkylsilyl groups having 1 to 5 carbon atoms, and alkoxysilyl groups having 1 to 5 carbon atoms, and these can also be used in combination. There are no particular limitations on the substitution positions of these substituents, and there are no limitations on the number of substituents.

[0015] In the above general formula (1) or (2), R 2 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms. R 2 Examples of the monovalent hydrocarbon group include linear, branched, or cyclic alkyl groups, alkenyl groups, aryl groups, and aralkyl groups. Specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, pentyl, hexyl, heptyl, octyl, and decyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, and 2-ethylhexyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, 1-propenyl, and 2-propenyl (allyl) groups; aryl groups such as phenyl, tolyl, and naphthyl groups; and aralkyl groups such as phenylmethyl and 2-phenylethyl groups. Among these, methyl, ethyl and phenyl groups are particularly preferred from the viewpoint of availability of raw materials, with methyl being even more preferred.

[0016] Some or all of the hydrogen atoms in each of the hydrocarbon groups may be substituted with other substituents, and specific examples of these substituents include alkoxy groups having 1 to 6 carbon atoms, such as methoxy, ethoxy, (iso)propoxy, and phenoxy; halogen atoms such as fluorine, chlorine, bromine, and iodine; cyano, amino, acyl, alkoxycarbonyl groups having 1 to 5 carbon atoms, carboxy, alkylsilyl groups having 1 to 5 carbon atoms, and alkoxysilyl groups having 1 to 5 carbon atoms, and these can also be used in combination. There are no particular limitations on the substitution positions of these substituents, and there are no limitations on the number of substituents.

[0017] In the above general formula (1) or (2), m is a positive number of 0 or less than 3, preferably 0 or less than 2, and more preferably 0 or a positive number of 1 or less. n is 0 or 1, preferably 0. Here, n+m is a positive number of 0 or less than 3, preferably 0 or less than 2, and more preferably 0 or 1 or less.

[0018] Specific examples of the compound (1) include 2-(2,3-dihydroxypropoxy)ethyl silanetriol polymer, 2-(2,3-dihydroxypropoxy)-1-methylethyl silanetriol polymer, 3-(2,3-dihydroxypropoxy)propyl silanetriol polymer, 4-(2,3-dihydroxypropoxy)butyl silanetriol polymer, 6-(2,3-dihydroxypropoxy)hexyl silanetriol polymer, and 8-(2,3-dihydroxypropoxy)octyl silanetriol polymer. (2,3-dihydroxypropoxy) alkyl silanetriol polymers such as ol polymers; 2-(2,3-dihydroxypropoxy) ethyl methyl silanediol polymer, 2-(2,3-dihydroxypropoxy)-1-methylethyl methyl silanediol polymer, 3-(2,3-dihydroxypropoxy) propyl methyl silanediol polymer, 4-(2,3-dihydroxypropoxy) butyl methyl silanediol polymer, 6-(2,3-dihydroxypropoxy) hexyl methyl silanediol polymer, (2,3-dihydroxypropoxy)alkyl silanediol polymers such as silanediol polymer and 8-(2,3-dihydroxypropoxy)octylmethyl silanediol polymer; dihydroxyalkyl silanetriol polymers such as 2,3-dihydroxypropyl silanetriol polymer, 2,3-dihydroxypropyl silanetriol polymer, 2,3-dihydroxy-1-methylpropyl silanetriol polymer, 2,3-dihydroxy-1-methylpropyl silanetriol polymer, 3,4-dihydroxybutyl silanetriol polymer, 3,4-dihydroxy-1-methylbutyl silanetriol polymer, 3,4-dihydroxy-1-methylbutyl silanetriol polymer, 3,4-dihydroxy-2-methylbutyl silanetriol polymer, 3,4-dihydroxy-2-methylbutyl silanetriol polymer, 4,5-dihydroxypentyl silanetriol polymer, 7,8-dihydroxyoctyl silanetriol polymer, and 9,10-dihydroxydecyl silanetriol polymer;Examples of dihydroxyalkyl silanediol polymers include 2,3-dihydroxypropylmethylsilanediol polymer, 2,3-dihydroxypropylmethylsilanediol polymer, 2,3-dihydroxy-1-methylpropylmethylsilanediol polymer, 2,3-dihydroxy-1-methylpropylmethylsilanediol polymer, 3,4-dihydroxybutylmethylsilanediol polymer, 3,4-dihydroxy-1-methylbutylmethylsilanediol polymer, 3,4-dihydroxy-2-methylbutylmethylsilanediol polymer, 4,5-dihydroxypentylmethylsilanediol polymer, 7,8-dihydroxypropylmethylsilanediol polymer, and 9,10-dihydroxydecylmethylsilanediol polymer.

[0019] Among these, from the viewpoint of easy availability of raw materials, 2-(2,3-dihydroxypropoxy)-1-methylethyl silanetriol polymer, 2-(2,3-dihydroxypropoxy)-1-methylethyl methyl silanediol polymer, 3-(2,3-dihydroxypropyl)propyl silanetriol polymer, 3-(2,3-dihydroxypropyl)propyl methyl silanediol polymer, 3,4-dihydroxybutyl silanetriol polymer, and 3,4-dihydroxybutyl methyl silanediol polymer are preferred, and 3-(2,3-dihydroxypropyl)propyl silanetriol polymer and 3-(2,3-dihydroxypropyl)propyl methyl silanediol polymer are more preferred.

[0020] Specific examples of the compound (2) include (3,4-dihydroxycyclohexyl)alkyl silanetriol polymers such as 1-(3,4-dihydroxycyclohexyl)ethyl silanetriol polymer, 2-(3,4-dihydroxycyclohexyl)ethyl silanetriol polymer, 2-(3,4-dihydroxycyclohexyl)propyl silanetriol polymer, 3-(3,4-dihydroxycyclohexyl)propyl silanetriol polymer, 4-(3,4-dihydroxycyclohexyl)butyl silanetriol polymer, 6-(3,4-dihydroxycyclohexyl)hexyl silanetriol polymer, and 8-(3,4-dihydroxycyclohexyl)octyl silanetriol polymer; 1-(3,4-dihydroxycyclohexyl)ethylmethyl silanediol polymer, 2-(3,4-dihydroxycyclohexyl)ethylmethyl silanediol polymer, and 2-(3,4-dihydroxycyclohexyl (3,4-dihydroxycyclohexyl)alkyl silanediol polymers such as 1-(3,4-dihydroxycyclohexyloxy)ethyl silanetriol polymer, 2-(3,4-dihydroxycyclohexyloxy)ethyl silanetriol polymer, 3-(3,4-dihydroxycyclohexyloxy)propyl silanetriol polymer, 4-(3,4-dihydroxycyclohexyl)butyl methyl silanediol polymer, 6-(3,4-dihydroxycyclohexyl)hexyl methyl silanediol polymer, and 8-(3,4-dihydroxycyclohexyl)octyl methyl silanediol polymer; (3,4-dihydroxycyclohexyloxy)alkyl silanetriol polymers such as 1-(3,4-dihydroxycyclohexyloxy)ethyl silanetriol polymer, 2-(3,4-dihydroxycyclohexyloxy)ethyl silanetriol polymer, 3-(3,4-dihydroxycyclohexyloxy)propyl silanetriol polymer, and 4-(3,4-dihydroxycyclohexyloxy)butyl silanetriol polymer;Examples of (3,4-dihydroxycyclohexyloxy)alkylsilanediol polymers include 1-(3,4-dihydroxycyclohexyloxy)ethylmethylsilanediol polymer, 2-(3,4-dihydroxycyclohexyloxy)ethylmethylsilanediol polymer, 3-(3,4-dihydroxycyclohexyloxy)propylmethylsilanediol polymer, and 4-(3,4-dihydroxycyclohexyloxy)butylmethylsilanediol polymer;

[0021] Among these, from the viewpoint of easy availability of raw materials, 1-(3,4-dihydroxycyclohexyl)ethyl silanetriol polymer, 1-(3,4-dihydroxycyclohexyl)ethyl methyl silanediol polymer, 2-(3,4-dihydroxycyclohexyl)ethyl silanetriol polymer, 2-(3,4-dihydroxycyclohexyl)ethyl methyl silanediol polymer, 3-(3,4-dihydroxycyclohexyl)propyl silanetriol polymer, 3-(3,4-dihydroxycyclohexyl)propyl methyl silanediol polymer, 2 -(3,4-dihydroxycyclohexyloxy)ethyl silanetriol polymer, 2-(3,4-dihydroxycyclohexyloxy)ethylmethyl silanediol polymer, 3-(3,4-dihydroxycyclohexyloxy)propyl silanetriol polymer, and 3-(3,4-dihydroxycyclohexyloxy)propylmethyl silanediol polymer are preferred, and 2-(3,4-dihydroxycyclohexyl)ethyl silanetriol polymer and 2-(3,4-dihydroxycyclohexyl)ethylmethyl silanediol polymer are more preferred.

[0022] On the other hand, the polysiloxane compound having an amino acid structure contained in the aqueous solution of the present invention is represented by the following general formula (3) (hereinafter referred to as "compound (3)").

[0023] [ka] (In the formula, R 2 , m and n have the same meanings as above.)

[0024] In the above general formula (3), R 3 , R 4 and R 5 each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms. R 3 , R 4 and R 5 As the monovalent hydrocarbon group, R 2 Examples of the monovalent hydrocarbon groups include the same groups as those exemplified above. Among these, from the viewpoint of easy availability of raw materials, a hydrogen atom and an unsubstituted linear alkyl group having 1 to 3 carbon atoms are preferred, and a hydrogen atom, a methyl group and an ethyl group are more preferred. In the above general formula (3), a is 0 or 1, and is preferably 1.

[0025] Specific examples of compound (3) include N-carboxymethyl-3-aminopropyl silanetriol polymer, N-(1-carboxyethyl)-3-aminopropyl silanetriol polymer, N-(1-carboxy-1-methylethyl)-3-aminopropyl silanetriol polymer, N-(2-carboxyethyl)-3-aminopropyl silanetriol polymer, N-(2-carboxy-1-methylethyl)-3-aminopropyl silanetriol polymer, and N-(2-carboxy-2-methylethyl)-3-aminopropyl silanetriol. aminopropyl silanetriol polymers having one carboxy group, such as N-(2-carboxy-1-phenylethyl)-3-aminopropyl silanetriol polymer and N-(2-carboxy-2-phenylethyl)-3-aminopropyl silanetriol polymer; N-carboxymethyl-3-aminopropyl methyl silanediol polymer, N-(1-carboxyethyl)-3-aminopropyl methyl silanediol polymer and N-(1-carboxy-1-methylethyl)-3-aminopropyl methyl silanediol polymer; aminopropyl silanediols having one carboxy group, such as N-(2-carboxyethyl)-3-aminopropylmethyl silanediol polymer, N-(2-carboxy-1-methylethyl)-3-aminopropylmethyl silanediol polymer, N-(2-carboxy-2-methylethyl)-3-aminopropylmethyl silanediol polymer, N-(2-carboxy-1-phenylethyl)-3-aminopropylmethyl silanediol polymer, and N-(2-carboxy-2-phenylethyl)-3-aminopropylmethyl silanediol polymer; Ol polymers: aminopropyl silanetriol polymers having two carboxy groups, such as N-(1,2-dicarboxyethyl)-3-aminopropyl silanetriol polymer and N-(2,3-dicarboxypropyl)-3-aminopropyl silanetriol polymer; and aminopropyl silanediol polymers having two carboxy groups, such as N-(1,2-dicarboxyethyl)-3-aminopropylmethyl silanediol polymer and N-(2,3-dicarboxypropyl)-3-aminopropylmethyl silanediol polymer.

[0026] Among these, from the viewpoint of easy availability of raw materials, aminopropyl silanetriol polymers having one carboxy group, such as N-carboxymethyl-3-aminopropyl silanetriol polymer, N-(2-carboxyethyl)-3-aminopropyl silanetriol polymer, N-(2-carboxyethyl)-3-aminopropylmethyl silanediol polymer, N-(2-carboxy-1-methylethyl)-3-aminopropyl silanetriol polymer, and N-(2-carboxy-2-methylethyl)-3-aminopropyl silanetriol polymer, and aminopropyl silanetriol polymers having two carboxy groups, such as N-(1,2-dicarboxyethyl)-3-aminopropyl silanetriol polymer and N-(2,3-dicarboxypropyl)-3-aminopropyl silanetriol polymer, are preferred.

[0027] The aqueous solution of the present invention may contain a polysiloxane compound containing both a 1,2-diol structure and an amino acid structure.

[0028] The aqueous solution of the present invention contains a polysiloxane compound having an amino acid structure, which is highly stable in aqueous solution, and therefore can prevent gelation of the polysiloxane compound having a 1,2-diol structure even if the aqueous solution becomes basic due to the addition of other components.

[0029] The aqueous solution of the present invention may contain a solvent other than water, if necessary. Examples of the solvent that can be used include alcohol solvents having 1 to 4 carbon atoms, such as methanol, ethanol, isopropanol, and tert-butanol; ether solvents, such as diethyl ether, tetrahydrofuran, and dioxane; ester solvents, such as ethyl acetate and butyl acetate; aprotic polar solvents, such as acetonitrile; and chlorinated hydrocarbon solvents, such as dichloromethane and chloroform. These solvents may be used alone or in combination.

[0030] The aqueous solution of the present invention may also contain inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, etc., or organic acids such as acetic acid, propionic acid, lactic acid, citric acid, etc. The content thereof is preferably 0.01 to 100 parts by mass, more preferably 0.05 to 50 parts by mass, and even more preferably 0.1 to 10 parts by mass, relative to 100 parts by mass of the aqueous solution.

[0031] The amount of compound (3) to be blended per 100 parts by mass of compound (1) or compound (2) is preferably 1 to 10,000 parts by mass, more preferably 10 to 1,000 parts by mass, and even more preferably 50 to 500 parts by mass, from the viewpoint of stabilizing the aqueous solution while maintaining the blending effect of compound (1) or (2).

[0032] The total mass of compound (1) or (2) and compound (3) relative to 100 parts by mass of water is preferably 0.01 to 500 parts by mass, more preferably 0.05 to 200 parts by mass, and even more preferably 0.1 to 100 parts by mass, from the viewpoints of efficiency during use and sufficient hydrolysis reaction.

[0033] Next, the method for producing the aqueous solution of the present invention will be described. The aqueous solution of the present invention can be obtained by mixing a silane compound having an epoxy structure represented by the following general formula (4) or (5) (hereinafter referred to as "compound (4)" or "compound (5)"), a silane compound having an amino acid ester structure represented by the following general formula (6) (hereinafter referred to as "compound (6)"), and water.

[0034] [ka] (In the formula, R 1 ~R 5 , a and n have the same meanings as above.)

[0035] In the above general formulas (4) to (6), R 6 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms. R 6 As the monovalent hydrocarbon group, R 2Examples of the monovalent hydrocarbon groups include the same groups as those exemplified above.

[0036] In the above general formula (6), R 7 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, and more preferably 1 to 3 carbon atoms, or a triorganosilyl group represented by the following general formula (7). -SiR 8 R 9 R 10 (7)

[0037] R 7 As the monovalent hydrocarbon group, R 2 Examples of the monovalent hydrocarbon groups include the same groups as those exemplified above. In the above general formula (7), R 8 , R 9 and R 10 each independently represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms. R 8 , R 9 and R 10 As the monovalent hydrocarbon group, R 2 Examples of the monovalent hydrocarbon groups include the same groups as those exemplified above.

[0038] Among these, R 8 , R 9 and R 10 As the group, an unsubstituted linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms; an alkenyl group; or an aryl group is preferable, and from the viewpoint of easy availability of raw materials in particular, an unsubstituted linear or branched alkyl group having 1 to 4 carbon atoms; or an alkenyl group is more preferable, and a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group is even more preferable.

[0039] Specific examples of the triorganosilyl group represented by the general formula (7) include trimethylsilyl, ethyldimethylsilyl, diethylmethylsilyl, triethylsilyl, tert-butyldimethylsilyl, triisopropylsilyl, hexyldimethylsilyl, octyldimethylsilyl, decyldimethylsilyl, octadecyldimethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, triphenylsilyl, and tert-butyldiphenylsilyl groups. Among these, from the viewpoint of easy availability of raw materials, a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a triisopropylsilyl group, and a tert-butyldiphenylsilyl group are more preferred, and a trimethylsilyl group and a triisopropylsilyl group are even more preferred.

[0040] Specific examples of the compound (4) include 2-glycidoxyethyltrimethoxysilane, 2-glycidoxyethyltriethoxysilane, 2-glycidoxy-1-methylethyltrimethoxysilane, 2-glycidoxy-1-methylethyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 4-glycidoxybutyltrimethoxysilane, 6-glycidoxyhexyltrimethoxysilane, and 8-glycidoxyoctyltrimethoxysilane. Trialkoxysilanes having a glycidoxy group, such as dimethyltrimethoxysilane; 2-glycidoxyethylmethyldimethoxysilane, 2-glycidoxyethylmethyldiethoxysilane, 2-glycidoxy-1-methylethylmethyldimethoxysilane, 2-glycidoxy-1-methylethylmethyldiethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 4-glycidoxybutylmethyldimethoxysilane, 6-glycidoxypropylmethyldimethoxysilane, 6-glycidoxypropylmethyldiethoxy ... Dialkoxysilanes having a glycidoxy group, such as hexylmethyldimethoxysilane and 8-glycidoxyoctylmethyldimethoxysilane; trialkoxysilanes having an epoxyalkyl group, such as 2,3-epoxypropyltrimethoxysilane, 2,3-epoxypropyltriethoxysilane, 2,3-epoxy-1-methylpropyltrimethoxysilane, 2,3-epoxy-1-methylpropyltriethoxysilane, 3,4-epoxybutyltrimethoxysilane, 3,4-epoxybutyltriethoxysilane, 3,4-epoxy-1-methylbutyltrimethoxysilane, 3,4-epoxy-1-methylbutyltriethoxysilane, 3,4-epoxy-2-methylbutyltrimethoxysilane, 3,4-epoxy-2-methylbutyltriethoxysilane, 4,5-epoxypentyltrimethoxysilane, 7,8-epoxyoctyltrimethoxysilane, 7,8-epoxypropylmethyldimethoxysilane, and 9,10-epoxydecyltrimethoxysilane;Dialkoxysilanes having an epoxy alkyl group such as 2,3-epoxypropylmethyldimethoxysilane, 2,3-epoxypropylmethyldiethoxysilane, 2,3-epoxy-1-methylpropylmethyldimethoxysilane, 2,3-epoxy-1-methylpropylmethyldiethoxysilane, 3,4-epoxybutylmethyldimethoxysilane, 3,4-epoxybutylmethyldiethoxysilane, 3,4-epoxy-1-methylbutylmethyldimethoxysilane, 3,4-epoxy-1-methylbutylmethyldiethoxysilane, 3,4-epoxy-2-methylbutylmethyldimethoxysilane, 3,4-epoxy-2-methylbutylmethyldiethoxysilane, 4,5-epoxypentylmethyldimethoxysilane, and 9,10-epoxydecylmethyldimethoxysilane are exemplified.

[0041] Among these, from the viewpoint of easy availability of raw materials, 2-glycidoxy-1-methylethyltrimethoxysilane, 2-glycidoxy-1-methylethylmethyldimethoxysilane, 2-glycidoxy-1-methylethyltriethoxysilane, 2-glycidoxy-1-methylethylmethyldiethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3,4-epoxybutyltrimethoxysilane, 3,4-epoxybutylmethyldimethoxysilane, 3,4-epoxybutyltriethoxysilane, and 3,4-epoxybutylmethyldiethoxysilane are preferred, and 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane, and 3-glycidoxypropylmethyldiethoxysilane are even more preferred.

[0042] Compound (4) may be commercially available or may be produced according to a conventionally known method, for example, by subjecting an alkenyl compound having an epoxy group to a hydrosilylation reaction with a hydrosilane compound.

[0043] Specific examples of the compound (5) include 1-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 1-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 2-(3,4-epoxycyclohexyl)propyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)propyltriethoxysilane, 3 ... (3,4-epoxycyclohexyl)alkyltrimethoxysilanes such as 1-(3,4-epoxycyclohexyl)propyltrimethoxysilane, 3-(3,4-epoxycyclohexyl)propyltriethoxysilane, 4-(3,4-epoxycyclohexyl)butyltrimethoxysilane, 4-(3,4-epoxycyclohexyl)butyltriethoxysilane, 6-(3,4-epoxycyclohexyl)hexyltrimethoxysilane, and 8-(3,4-epoxycyclohexyl)octyltrimethoxysilane; 3,4-Epoxycyclohexyl)ethylmethyldimethoxysilane, 1-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)propylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)propylmethyldiethoxysilane, 3-(3,4-epoxycyclohexyl (3,4-epoxycyclohexyl)alkyldimethoxysilanes such as propylmethyldimethoxysilane, 3-(3,4-epoxycyclohexyl)propylmethyldiethoxysilane, 4-(3,4-epoxycyclohexyl)butylmethyldimethoxysilane, 4-(3,4-epoxycyclohexyl)butylmethyldiethoxysilane, 6-(3,4-epoxycyclohexyl)hexylmethyldimethoxysilane, and 8-(3,4-epoxycyclohexyl)octylmethyldimethoxysilane;(3,4-epoxycyclohexyloxy)alkyltrimethoxysilanes such as 1-(3,4-epoxycyclohexyloxy)ethyltrimethoxysilane, 1-(3,4-epoxycyclohexyloxy)ethyltriethoxysilane, 2-(3,4-epoxycyclohexyloxy)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyloxy)ethyltriethoxysilane, 3-(3,4-epoxycyclohexyloxy)propyltrimethoxysilane, 3-(3,4-epoxycyclohexyloxy)propyltriethoxysilane, 4-(3,4-epoxycyclohexyloxy)butyltrimethoxysilane, and 4-(3,4-epoxycyclohexyloxy)butyltriethoxysilane; 1-(3, Examples of (3,4-epoxycyclohexyloxy)alkyldimethoxysilanes include 4-epoxycyclohexyloxy)ethylmethyldimethoxysilane, 1-(3,4-epoxyhexyloxy)ethylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyloxy)ethylmethyldimethoxysilane, 2-(3,4-epoxyhexyloxy)ethylmethyldiethoxysilane, 3-(3,4-epoxycyclohexyloxy)propylmethyldimethoxysilane, 3-(3,4-epoxyhexyloxy)propylmethyldiethoxysilane, 4-(3,4-epoxycyclohexyloxy)butylmethyldimethoxysilane, and 4-(3,4-epoxyhexyloxy)butylmethyldiethoxysilane;

[0044] Among these, from the viewpoint of easy availability of raw materials, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane, 3-(3,4-epoxycyclohexyl)propyltrimethoxysilane, 3-(3,4-epoxycyclohexyl)propylmethyldimethoxysilane, 3-(3,4-epoxycyclohexyl)propyltriethoxysilane, 3-(3,4-epoxycyclohexyl)propylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyloxy)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyloxy)ethylmethyldimethoxysilane,

[0043] Preferred are 2-(3,4-epoxycyclohexyloxy)ethyltriethoxysilane, 2-(3,4-epoxyhexyloxy)ethylmethyldiethoxysilane, 3-(3,4-epoxycyclohexyloxy)propyltrimethoxysilane, 3-(3,4-epoxycyclohexyloxy)propylmethyldimethoxysilane, 3-(3,4-epoxycyclohexyloxy)propyltriethoxysilane, and 3-(3,4-epoxyhexyloxy)propylmethyldiethoxysilane, and more preferred are 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, and 2-(3,4-epoxycyclohexyl)ethylmethyldiethoxysilane.

[0045] Compound (5) may be commercially available or may be produced according to a conventionally known method, for example, by subjecting an alkenyl compound having an epoxy group to a hydrosilylation reaction with a hydrosilane compound.

[0046] Specific examples of the compound (6) include N-(methoxycarbonylmethyl)-3-aminopropyltrimethoxysilane, N-(methoxycarbonylmethyl)-3-aminopropyltriethoxysilane, N-(ethoxycarbonylmethyl)-3-aminopropyltrimethoxysilane, N-(ethoxycarbonylmethyl)-3-aminopropyltriethoxysilane, N-(trimethylsiloxycarbonylmethyl)-3-aminopropyltrimethoxysilane, N-(trimethylsiloxycarbonylmethyl)-3-aminopropyltriethoxysilane, N-(triethylsiloxycarbonylmethyl)-3-aminopropyltriethoxysilane, N-(triisopropylsiloxycarbonylmethyl)-3-aminopropyltrimethoxysilane, N-(1-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(1-methoxycarbonyl-1-methylethyl)-3-aminopropyltrimethoxysilane, N-(2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-methoxycarbonylethyl)-3-aminopropyltriethoxysilane, N-(2-ethoxycarbonylethyl)-3-aminopropyltriethoxysilane N-(2-ethoxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-trimethylsiloxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-trimethylsiloxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-trimethylsiloxycarbonylethyl)-3-aminopropyltriethoxysilane, N-(2-triethylsiloxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-triisopropyl aminopropyltrialkoxysilanes having one alkoxycarbonyl group, such as N-(2-methoxycarbonyl-2-methylethyl)-3-aminopropyltrimethoxysilane, N-(2-methoxycarbonyl-2-phenylethyl)-3-aminopropyltrimethoxysilane, N-(1-methyl-2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, and N-(1-phenyl-2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane;N-(Methoxycarbonylmethyl)-3-aminopropylmethyldimethoxysilane, N-(Methoxycarbonylmethyl)-3-aminopropylmethyldiethoxysilane, N-(Ethoxycarbonylmethyl)-3-aminopropylmethyldimethoxysilane, N-(Ethoxycarbonylmethyl)-3-aminopropylmethyldiethoxysilane, N-(Trimethylsiloxycarbonylmethyl)-3-aminopropylmethyldimethoxysilane, N-(Trimethylsiloxycarbonylmethyl)-3-aminopropylmethyldiethoxy Sisilane, N-(triethylsiloxycarbonylmethyl)-3-aminopropylmethyldimethoxysilane, N-(triisopropylsiloxycarbonylmethyl)-3-aminopropylmethyldimethoxysilane, N-(1-methoxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, N-(1-methoxycarbonyl-1-methylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-methoxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-methoxycarbonyl N-(2-ethoxycarbonylethyl)-3-aminopropylmethyldiethoxysilane, N-(2-ethoxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-ethoxycarbonylethyl)-3-aminopropylmethyldiethoxysilane, N-(2-trimethylsiloxycarbonylethyl)-3-aminopropylmethyldiethoxysilane, N-(2-triethylsiloxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-triisopropylsiloxycarbonylethyl)-3-aminopropyl aminopropyldialkoxysilanes having one alkoxycarbonyl group, such as methyldimethoxysilane, N-(2-methoxycarbonyl-2-methylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-methoxycarbonyl-2-phenylethyl)-3-aminopropylmethyldimethoxysilane, N-(1-methyl-2-methoxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, and N-(1-phenyl-2-methoxycarbonylethyl)-3-aminopropylmethyldimethoxysilane;Examples of such alkoxycarbonyl groups include aminopropyltrialkoxysilanes having two alkoxycarbonyl groups, such as N-[1,2-bis(methoxycarbonyl)ethyl]-3-aminopropyltrimethoxysilane and N-[2,3-bis(methoxycarbonyl)propyl]-3-aminopropyltrimethoxysilane; and aminopropyldialkoxysilanes having two alkoxycarbonyl groups, such as N-[1,2-bis(methoxycarbonyl)ethyl]-3-aminopropylmethyldimethoxysilane and N-[2,3-bis(methoxycarbonyl)propyl]-3-aminopropylmethyldimethoxysilane.

[0047] Among these, from the viewpoint of the ease of availability of raw materials, N-(methoxycarbonylmethyl)-3-aminopropyltrimethoxysilane, N-(methoxycarbonylmethyl)-3-aminopropylmethyldimethoxysilane, N-(2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-methoxycarbonylethyl)-3-aminopropylmethyldimethoxysilane, N-(2-ethoxycarbonylethyl)-3-aminopropyltriethoxysilane, N-(2-trimethylsiloxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-triisopropylsilane) Preferred are N-(propylsiloxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(2-methoxycarbonyl-2-methylethyl)-3-aminopropyltrimethoxysilane, N-(1-methyl-2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-(1-phenyl-2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, N-[1,2-bis(methoxycarbonyl)ethyl]-3-aminopropyltrimethoxysilane, and N-[2,3-bis(methoxycarbonyl)propyl]-3-aminopropyltrimethoxysilane.

[0048] Compound (6) may be commercially available or may be produced by a conventional method, such as an addition reaction between an aminosilane compound and an unsaturated ester compound, or a substitution reaction between an aminosilane compound and a halogenated acetate compound.

[0049] The method for mixing compound (4) or (5), compound (6), and water is not particularly limited, and examples thereof include a method in which compound (4) or compound (5), and compound (6) are mixed with water to prepare respective aqueous solutions, and then these aqueous solutions are mixed; a method in which compound (4) or compound (5) and water are mixed in advance to prepare an aqueous solution, and then this aqueous solution is mixed with compound (6); and a method in which compound (6) and water are mixed in advance to prepare an aqueous solution, and then this aqueous solution is mixed with compound (4) or compound (5). In this case, since the amino acid structure of the product compound (3) affects the stability of the aqueous solution, it is preferable to mix compound (6) with water before mixing with compound (4) or (5).

[0050] The pressure and temperature during mixing are not particularly limited, but are preferably 0 to 120°C, more preferably 10 to 60°C, under normal pressure. Although no catalyst is particularly required, inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid; and organic acids such as acetic acid, propionic acid, lactic acid, and citric acid may be added.

[0051] When mixing, a solvent other than water can be used as needed. Examples of solvents that can be used include alcohol solvents having 1 to 4 carbon atoms, such as methanol, ethanol, isopropanol, and tert-butanol; ether solvents, such as diethyl ether, tetrahydrofuran, and dioxane; ester solvents, such as ethyl acetate and butyl acetate; aprotic polar solvents, such as acetonitrile; and chlorinated hydrocarbon solvents, such as dichloromethane and chloroform. These solvents may be used alone or in combination of two or more.

[0052] If necessary, the produced alcohol, water, solvents other than water, and catalyst can be removed from the aqueous solution obtained as described above. The removal method is not particularly limited, and examples thereof include distillation, filtration, etc. The removal may be carried out by one of these methods alone or by combining two or more of them. The pressure and temperature during distillation are not particularly limited, but are preferably normal pressure or reduced pressure, and are preferably 0 to 250°C, more preferably 50 to 200°C. [Example]

[0053] The present invention will be specifically explained below by showing synthesis examples, examples and comparative examples, but the present invention is not limited to the following examples.

[0054] [1] Preparation of an aqueous solution containing a water-soluble polysiloxane compound having an amino acid structure (compound (3)) [Synthesis Example 1] Synthesis of an aqueous solution containing N-(2-carboxyethyl)-3-aminopropylsilanetriol and its condensate A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 79.7 g of water, and 53.1 g (0.2 mol) of compound (6), N-(2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane, was added. The resulting reaction solution was distilled under atmospheric pressure to remove the methanol and water produced by hydrolysis. Water was added to adjust the concentration of the resulting aqueous solution to 50% by mass, yielding 76.8 g of an aqueous solution (aqueous solution 1) containing N-(2-carboxyethyl)-3-aminopropylsilanetriol polymer.

[0055] [Synthesis Example 2] Synthesis of an aqueous solution containing N-(2-carboxy-2-methylethyl)-3-aminopropylsilanetriol and its condensate A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 40.0 g of water, and 20.0 g (0.072 mol) of compound (6), N-(2-methoxycarbonyl-2-methylethyl)-3-aminopropyltrimethoxysilane, was added. The resulting reaction solution was distilled under atmospheric pressure to remove the methanol and water produced by hydrolysis. Water was added to adjust the concentration of the resulting aqueous solution to 50% by mass, yielding 30.6 g of an aqueous solution (aqueous solution 2) containing N-(2-carboxy-2-methylethyl)-3-aminopropylsilanetriol polymer.

[0056] [Synthesis Example 3] Synthesis of an aqueous solution containing N-(1-methyl-2-carboxyethyl)-3-aminopropylsilanetriol and its condensate A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 40.0 g of water and then 20.0 g (0.072 mol) of N-(1-methyl-2-methoxycarbonylethyl)-3-aminopropyltrimethoxysilane was added. The resulting reaction solution was distilled under atmospheric pressure to remove the methanol and water produced by hydrolysis. Water was added to adjust the concentration of the resulting aqueous solution to 50% by mass, yielding 26.6 g of an aqueous solution containing N-(1-methyl-2-carboxyethyl)-3-aminopropylsilanetriol polymer (aqueous solution 3).

[0057] [Synthesis Example 4] Synthesis of an aqueous solution containing N-(2,3-dicarboxypropyl)-3-aminopropylsilanetriol and its condensate A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 50.0 g of water, and 25.0 g (0.074 mol) of compound (6), N-[2,3-bis(methoxycarbonyl)propyl]-3-aminopropyltrimethoxysilane, was added. The resulting reaction solution was distilled under atmospheric pressure to remove the methanol and water produced by hydrolysis. Water was added to adjust the concentration of the resulting aqueous solution to 50% by mass, yielding 36.2 g of an aqueous solution (aqueous solution 4) containing N-(2,3-dicarboxypropyl)-3-aminopropylsilanetriol polymer.

[0058] [Examples 1 to 8] The compounds used in the examples are shown below. (1) Silane compound having an epoxy structure (compound (4) or (5)) KBM-403 (compound (4)): 3-Glycidoxypropyltrimethoxysilane (Shin-Etsu Chemical Co., Ltd.) KBM-402 (compound (4)): 3-Glycidoxypropylmethyldimethoxysilane (Shin-Etsu Chemical Co., Ltd.) (2) Water-soluble polysiloxane compound having an amino acid structure (compound (3)) Aqueous solution 1: Synthesis example 1 Aqueous solution 2: Synthesis example 2 Aqueous solution 3: Synthesis example 3 Aqueous solution 4: Synthesis example 4

[0059] A silane compound having an epoxy structure corresponding to compound (4), water, and acetic acid were weighed out in the ratios shown in Table 1 below and mixed using a vortex mixer to obtain an aqueous solution. To the obtained aqueous solution, each aqueous solution containing a water-soluble polysiloxane compound having an amino acid structure corresponding to compound (3) was added in the ratios shown in Table 1 below. A 25% by mass aqueous solution of sodium hydroxide was added to this aqueous solution in the ratios shown in Table 1 below and mixed to prepare an aqueous solution. The storage stability of these aqueous solutions was evaluated as follows.

[0060] [Storage stability] The prepared aqueous solutions were allowed to stand at 20° C. and evaluated according to the following criteria. The results are also shown in Table 1. ○: No gel formation occurs for 3 days or more after preparation. △: Gel forms between 24 hours and 3 days after preparation. ×: Gel formed within 24 hours after preparation.

[0061] [Comparative Examples 1 to 4] Aqueous solutions were prepared in the same manner as in Examples 1 to 8, except that an aqueous solution containing a water-soluble polysiloxane compound having an amino acid structure corresponding to compound (3) was not included, or instead of this aqueous solution, KBP-90 (an aqueous solution of a silane compound having a primary amino group, manufactured by Shin-Etsu Chemical Co., Ltd.) was used and mixed in the ratios shown in Table 1 below.

[0062] [Table 1]

[0063] As shown in Table 1, the aqueous solution of the Example to which an aqueous solution containing a polysiloxane compound having an amino acid structure corresponding to compound (3) was added did not form a gel even when the aqueous solution became basic, and had high storage stability, compared to the aqueous solution of Comparative Example 1 which did not contain compound (3) and the aqueous solution of Comparative Example 2 to which an aqueous solution containing a polysiloxane compound having a primary amino group was added.

[0064] [Examples 9 to 12 and Comparative Examples 5 to 6] Aqueous solutions were prepared in the same manner as in Examples 1 to 8, except that KBM-303 (2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.), which corresponds to compound (5), was used as the silane compound having an epoxy structure and mixed in the ratio shown in Table 2 below, and the storage stability was evaluated.

[0065] [Table 2]

[0066] As shown in Table 2, the aqueous solutions of the Examples to which an aqueous solution containing a polysiloxane compound having an amino acid structure corresponding to compound (3) was added did not form gels even when the aqueous solutions became basic, and had high storage stability, compared to the aqueous solution of Comparative Example 5 which did not contain compound (3) and the aqueous solution of Comparative Example 6 which contained an aqueous solution containing a polysiloxane compound having a primary amino group.

Claims

1. An aqueous solution containing a polysiloxane compound having a 1,2-diol structure represented by the following general formula (1) or (2) and a polysiloxane compound having an amino acid structure represented by the following general formula (3): 【Chemistry 1】 (In the formula, R 1 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom; R 2 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, m is 0 or a positive number less than 3, n is 0 or 1, and n+m is 0 or a positive number less than 3. 【Chemistry 2】 (In the formula, R 1 , R 2 , m and n have the same meanings as above.) 【Transformation 3】 (In the formula, R 2 , m and n have the same meanings as above, R 3 , R 4 and R 5 each independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, and a is 0 or 1.

2. 2. The aqueous solution according to claim 1, comprising 1 to 10,000 parts by mass of the polysiloxane compound having an amino acid structure per 100 parts by mass of the polysiloxane compound having a 1,2-diol structure.

3. 2. The aqueous solution according to claim 1, wherein the total mass of the polysiloxane compound having a 1,2-diol structure and the polysiloxane compound having an amino acid structure is 0.01 to 100 parts by mass per 100 parts by mass of water.

4. 3. A method for producing the aqueous solution according to claim 1, comprising mixing a silane compound having an epoxy structure represented by the following general formula (4) or (5), a silane compound having an amino acid ester structure represented by the following general formula (6), and water: 【Chemistry 4】 (In the formula, R 1 , R 2 and n have the same meaning as above, R 6 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. 【Transformation 5】 (In the formula, R 1 , R 2 , R 6 and n have the same meaning as above. 【Transformation 6】 [(wherein, R 2 ~R 6 , a and n have the same meanings as above, R 7 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms or a group represented by the following general formula (7): -SiR 8 R 9 R 10 (7) (In the formula, R 8 , R 9 and R 10 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. represents a triorganosilyl group represented by the following formula:

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