Aqueous composition and method for producing same

Abstract

This aqueous composition contains: a silanol compound having an imidazolidinone group represented by general formula (1); and a condensate of the silanol compound. The content of an alcohol is less than 5 mass% relative to the content of the silanol compound and the condensate of the silanol compound. The aqueous composition suppresses the generation of alcohols, suppresses excessive condensation of the silanol compound, prevents an increase in molecular weight over time, and yields a colorless transparent aqueous solution. (In the formula, R1 denotes a halogen atom or a methyl group, R2 denotes an unsubstituted divalent hydrocarbon group having 1-8 carbon atoms, and n denotes an integer between 0 and 2.)

Description

[Technical field]

[0001] The present invention relates to an aqueous composition and a method for producing the same, and more specifically, to an aqueous composition containing a silanol compound and a condensate of a silanol compound and a method for producing the same. [Background technology]

[0002] In an organosilicon compound having a hydrolyzable silyl group and an organic group, a silanol group generated by hydrolysis of the hydrolyzable silyl group forms a covalent bond with a hydroxyl group on the surface of an inorganic material, and the organic group further reacts with the organic material, making it possible to bond organic materials and inorganic materials that are usually difficult to bond together. This makes it possible to impart properties such as heat resistance, water resistance, weather resistance, improved mechanical strength, adhesion, dispersibility, hydrophobicity, and rust resistance to the organic-inorganic composite material. 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, imidazolidinone silane compounds, which are organosilicon compounds having an imidazolidinone group, can enhance the adhesion of organic-inorganic composite materials because the imidazolidinone group exhibits high compatibility with various organic and inorganic materials. Examples of such imidazolidinone silane compounds include 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone and 1-[3-(dimethoxymethylsilyl)propyl]-2-imidazolidinone (Patent Document 1). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent No. 3,209,053 Summary of the Invention [Problem to be solved by the invention]

[0005] However, the imidazolidinone silane compound having an alkoxysilyl group described in Patent Document 1 generates a considerable amount of alcohol due to hydrolysis of the alkoxysilyl group. In recent years, reduction of volatile organic compounds (VOCs) has been raised as a major theme in environmental issues closely related to global warming, health problems, etc., and the imidazolidinone silane compound generates a large amount of alcohol, raising concerns about the burden on the environment. In addition, the alcohol generated by hydrolysis may reduce the compatibility of the imidazolidinone silane compound with various organic or inorganic materials, and the desired effects derived from the imidazolidinone group may not be fully exerted.

[0006] One method for reducing the amount of alcohol generated from an alkoxysilane compound, which is an organosilicon compound having an alkoxysilyl group, is to hydrolyze the alkoxysilane compound to generate a silanol compound, which is an organosilicon compound having a silanol group, and then remove the generated alcohol to prepare an aqueous composition containing the silanol compound, a condensate of the silanol compound, and water.

[0007] However, in the case of an alkoxysilane compound having an organic group such as an alkyl group, an aryl group, an alkenyl group, an epoxy group, a mercapto group, or a (meth)acrylic group; a secondary or tertiary amino group such as an arylamino group; or a urea skeleton such as an isocyanurate ring or a glycoluril ring, the silanol groups condense irreversibly after the hydrolysis reaction, so that the aqueous solution becomes high molecular weight with time, and the state of a uniform aqueous composition cannot be maintained. That is, in the hydrolysis reaction of a trialkoxysilane compound or a dialkoxysilane compound having the above organic group, a secondary or tertiary amino group, or a urea skeleton, a trisilanol compound or a disilanol compound is generated. These silanol compounds generate silanol condensates having a linear, branched, cyclic, or three-dimensional network structure by condensing the silanol groups. Furthermore, as the condensation progresses, these silanol condensates grow into a solid (gel-like substance) or liquid (oil-like substance) high molecular weight substance that is poorly compatible with the aqueous solution, so that the aqueous solution cannot be maintained in a chemically stable state (uniform state). In addition, the alcohol generated by hydrolysis reacts with the silanol compound to regenerate the alkoxysilane compound, and thus plays a role in temporarily suppressing the increase in molecular weight of the aqueous solution over time. However, when the alcohol is removed from the aqueous solution, the condensation between the silanol groups accelerates, resulting in a significant increase in the amount of the above-mentioned high molecular weight compounds.

[0008] In this respect, in the hydrolysis of an alkoxysilane compound having a primary amino group such as an amino group or an alkylenediamino group, the condensation between silanol groups reaches equilibrium, so that the resulting silanol condensate does not grow into a high molecular weight substance with low compatibility with aqueous solutions. This allows the aqueous solution to remain chemically stable. Furthermore, it is possible to remove alcohol from the aqueous solution, so this is useful as one of the methods for reducing the amount of alcohol generated from an alkoxysilane compound.

[0009] However, although an alkoxysilane compound having a primary amino group can be used to prepare an aqueous solution in a chemically stable state in which high molecular weight substances having low compatibility with aqueous solutions are not generated, the appearance of the aqueous solution turns yellow over time, and therefore the compound cannot be used in applications requiring colorless transparency.

[0010] Therefore, there has been a demand for the development of a colorless, transparent aqueous composition that suppresses the generation of alcohol and the excessive condensation of silanol compounds, thereby preventing the increase in molecular weight that occurs with the passage of time.

[0011] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an aqueous composition which can prepare a colorless, transparent aqueous solution while suppressing the generation of alcohol and excessive condensation of a silanol compound, thereby preventing the increase in molecular weight that occurs with changes over time, and a method for producing the same. [Means for solving the problem]

[0012] As a result of intensive research conducted by the present inventors to achieve the above-mentioned object, they have found that an aqueous composition containing a silanol compound having an imidazolidinone group and a condensate of the silanol compound is an aqueous composition which suppresses the generation of alcohol while suppressing excessive condensation of the silanol compound, thereby preventing the increase in molecular weight that occurs with changes over time, and which is capable of preparing a colorless, transparent aqueous solution, and thus completed the present invention.

[0013] That is, the present invention provides 1. The following general formula (1) [ka] (In the formula, R 1 represents a halogen atom or a methyl group, R 2 represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms, and n represents an integer of 0 to 2. and a condensate of the silanol compound, an aqueous composition having an alcohol content of less than 5 mass% based on the silanol compound and the condensate of the silanol compound; 2. The following general formula (2) [ka] (In the formula, R 1 , R 2 and n have the same meaning as above, R 3 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms. A method for producing an aqueous composition according to claim 1, comprising the steps of hydrolyzing an imidazolidinone silane compound represented by the formula: 3. The method for producing the aqueous composition according to 2, wherein the amount of water is 3 to 100,000 moles per mole of silicon atom of the imidazolidinone silane compound. to provide. Effect of the Invention

[0014] The aqueous composition of the present invention does not generate alcohol, and suppresses excessive condensation of the silanol compound, thereby preventing the increase in molecular weight that occurs with the passage of time, and can maintain a chemically stable state. In addition, an aqueous solution prepared from the aqueous composition of the present invention has a transparent appearance and does not yellow over time, and therefore can be used in applications requiring colorless transparency. Furthermore, since the imidazolidinone group in the aqueous composition of the present invention exhibits high compatibility with various organic and inorganic materials, when the aqueous composition is used as a silane coupling agent, a surface treatment agent, or the like, it can enhance the adhesion of organic-inorganic composite materials. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] The present invention will be specifically described below. The aqueous composition of the present invention contains a silanol compound having an imidazolidinone group and a condensate thereof.

[0016] In the aqueous composition of the present invention, the silanol compound having an imidazolidinone group is a silanol compound having an imidazolidinone group represented by the following general formula (1) (hereinafter referred to as "compound (1)").

[0017] [ka]

[0018] In the general formula (1), R 1 represents a halogen atom such as a chlorine atom, a bromine atom or an iodine atom, or a methyl group, with the methyl group being preferred from the viewpoint of availability. R 2 represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 to 4 carbon atoms. The divalent hydrocarbon group may be linear, branched, or cyclic, and specific examples thereof include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, and octamethylene; branched alkylene groups such as sec-propylene, sec-butylene, tert-butylene, sec-pentylene, tert-pentylene, sec-hexylene, tert-hexylene, sec-heptylene, tert-heptylene, sec-octylene, and tert-octylene; and cyclic alkylene groups such as cyclopropylene, cyclopentylene, and cyclohexylene. Among these, R 2 As the alkyl group, an unsubstituted linear alkylene group having 1 to 5 carbon atoms is preferable, and from the viewpoint of easy availability, an unsubstituted linear alkylene group having 1 to 4 carbon atoms such as a methylene group or an ethylene group is more preferable.

[0019] Furthermore, n is an integer of 0 to 2, but is preferably 0 or 1 from the viewpoint of increasing adhesion by reacting with multiple hydroxyl groups on the substrate surface, particularly when used as a silane coupling agent or surface treatment agent.

[0020] Specific examples of the compound (1) include 1-[3-(trihydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)methyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)ethyl]-2-imidazolidinone, Dazolidinone, 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)propyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)butyl]-2-imidazolidinone, 1 -[3-(trihydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)hexyl]-2-imidazolidinone, 1-[3- silanol compounds such as (trihydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(hydroxydimethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)octyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)octyl]-2-imidazolidinone, and 1-[3-(hydroxydimethylsilyl)octyl]-2-imidazolidinone;1-[3-(fluorodihydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(fluorodihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(fluoro 1-[3-(difluorohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(fluorodihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(fluorodihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(fluorodihydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(fluorodihydroxysilyl)hexyl]-2-imidazolidinone fluorosilanol compounds such as 1-[3-(difluorohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(fluorohydroxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(fluorodihydroxysilyl)octyl]-2-imidazolidinone, 1-[3-(difluorohydroxysilyl)octyl]-2-imidazolidinone, and 1-[3-(fluorohydroxymethylsilyl)octyl]-2-imidazolidinone;1-[3-(chlorodihydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(chlorodihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(chlorodihydroxysilyl)ethyl]-2-imidazolidinone 1-[3-(dichlorohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(chlorodihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(chlorodihyd 1-[3-(dichlorohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(chlorodihydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(chlorodihy chlorosilanol compounds such as 1-[3-(dichlorohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(chlorohydroxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(chlorodihydroxysilyl)octyl]-2-imidazolidinone, 1-[3-(dichlorohydroxysilyl)octyl]-2-imidazolidinone, and 1-[3-(chlorohydroxymethylsilyl)octyl]-2-imidazolidinone;1-[3-(bromodihydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(bromodihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)ethyl]-2-imidazolidinone 1-[3-(dibromohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(bromodihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(bromodihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(bromodihydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(bromodihydroxysilyl)hexyl]-2-imidazolidinone, bromosilanol compounds such as 1-[3-(dibromohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(bromohydroxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(bromodihydroxysilyl)octyl]-2-imidazolidinone, 1-[3-(dibromohydroxysilyl)octyl]-2-imidazolidinone, and 1-[3-(bromohydroxymethylsilyl)octyl]-2-imidazolidinone;1-[3-(iododihydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)propyl]-2-imidazolidinone 1-[3-(iodohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)hexyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)hexyl]-2-imidazolidinone Examples of the iodosilanol compounds include 1-[3-(diiodohydroxysilyl)heptyl]-2-imidazolidinone, 1-[3-(iodohydroxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(iododihydroxysilyl)octyl]-2-imidazolidinone, 1-[3-(diiodohydroxysilyl)octyl]-2-imidazolidinone, and 1-[3-(iodohydroxymethylsilyl)octyl]-2-imidazolidinone;

[0021] Among these, in particular when used as a silane coupling agent or surface treatment agent, from the viewpoint of increasing adhesion by reacting with multiple hydroxyl groups on the substrate surface, 1-[3-(trihydroxysilyl)methyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone, [3-(trihydroxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dihydroxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)hexyl]-2-imidazolidinone, and 1-[3-(dihydroxymethylsilyl)hexyl]-2-imidazolidinone are preferred, and 1-[3-(trihydroxysilyl)methyl]-2-imidazolidinone and 1- Particularly preferred are [3-(trihydroxysilyl)ethyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)butyl]-2-imidazolidinone, 1-[3-(trihydroxysilyl)pentyl]-2-imidazolidinone, and 1-[3-(trihydroxysilyl)hexyl]-2-imidazolidinone.

[0022] The content of compound (1) in the aqueous composition is not particularly limited as long as it is an amount that reacts with multiple hydroxyl groups on the surface of a substrate to enhance adhesion when used as a silane coupling agent, a surface treatment agent, or the like. From the viewpoint of productivity, the content is preferably in the range of 0.0001 to 99 mass%, more preferably 0.01 to 99 mass%, and even more preferably 1 to 99 mass%, based on the aqueous composition.

[0023] The condensate of compound (1) in the aqueous composition is a compound formed by dehydration condensation of hydroxyl groups within the above compound (1) molecules. Specific examples of the condensation product of compound (1) include linear, branched, cyclic and three-dimensional network polysiloxanes such as disiloxane, trisiloxane, tetrasiloxane, pentasiloxane, hexasiloxane, heptasiloxane, octasiloxane, nonasiloxane and decasiloxane.

[0024] Specific examples of polysiloxanes include 1,1,3,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)methyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)methyl]-1,3-dimethyldisiloxane, 1,1,3,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)ethyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)ethyl]-1,3-dimethyldisiloxane, 1,1,3,3-tetrahydroxy-1,3-bis[3-( 2-imidazolidino)propyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)propyl]-1,3-dimethyldisiloxane, 1,1,3,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)butyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)butyl]-1,3-dimethyldisiloxane, 1,1,3,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)pentyl]-disiloxane, 1,3-dihydroxy-1,3-bis[ 3-(2-imidazolidino)pentyl]-1,3-dimethyldisiloxane, 1,1,3,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)hexyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)hexyl]-1,3-dimethyldisiloxane, 1,1,3,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)heptyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)heptyl]-1,3-dimethyldisiloxane, 1,1,3 Disiloxanes such as 1,3-tetrahydroxy-1,3-bis[3-(2-imidazolidino)octyl]-disiloxane, 1,3-dihydroxy-1,3-bis[3-(2-imidazolidino)octyl]-1,3-dimethyldisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2-imidazolidino)methyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)methyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-Tris[3-(2-imidazolidino)ethyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)ethyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2-imidazolidino)propyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)propyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2 -imidazolidino)butyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)butyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2-imidazolidino)pentyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)pentyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2-imidazolidino)hexyl] xyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)hexyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2-imidazolidino)heptyl]-trisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)heptyl]-1,3,5-trimethyltrisiloxane, 1,1,3,5,5-pentahydroxy-1,3,5-tris[3-(2-imidazolidino)octyl]-trisiloxane 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)octyl]-1,3,5-trimethyltrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)methyl]-cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)ethyl]-cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)propyl]-cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-Tris[3-(2-imidazolidino)butyl]cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)pentyl]cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)hexyl]cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)heptyl]cyclotrisiloxane, 1,3,5-trihydroxy-1,3,5-tris[3-(2-imidazolidino)octyl]cyclotrisiloxane San, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)methyl]-cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)ethyl]-cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)propyl]-cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)butyl]-cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)pentyl] -cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)hexyl]-cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)heptyl]-cyclotrisiloxane, 1,3,5-trimethyl-1,3,5-tris[3-(2-imidazolidino)octyl]-cyclotrisiloxane, and other trisiloxanes; 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)methyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)methyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)ethyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)propyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)butyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)pentyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-Tetra[3-(2-imidazolidino)hexyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)heptyl]-cyclotetrasiloxane, 1,3,5,7-tetrahydroxy-1,3,5,7-tetra[3-(2-imidazolidino)octyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)methyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2- imidazolidino)ethyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)propyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)butyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)pentyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)hexyl]-cyclotetrasiloxane Tetrasiloxanes such as 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)heptyl]-cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetra[3-(2-imidazolidino)octyl]-cyclotetrasiloxane; 1,1,3,5,7,9,9-heptahydroxy-1,3,5,7,9-pentakis[3-(2-imidazolidino)methyl]-pentasiloxane; 1,1,3,5,7,9,11,11-octahydroxy-1,3,5,7,9,11-hexakis 1,1,3,5,7,9,11,13,13-Nonahydroxy-1,3,5,7,9,11,13-Heptakis[3-(2-imidazolidino)methyl]-heptasiloxane;1,1,3,5,7,9,11,13,15,15-Decahydroxy-1,3,5,7,9,11,13,15-Octakis[3-(2-imidazolidino)methyl]-octasiloxane;1,1,3,5,7,9,11,13,15,17,17-Undecahydroxy-1,3,5,7,9,11,13,15,Examples of such compounds include 17-nonakis[3-(2-imidazolidino)methyl]-nonasiloxane; 1,1,3,5,7,9,11,13,15,17,19,19-dodecahydroxy-1,3,5,7,9,11,13,15,17,19-decakis[3-(2-imidazolidino)methyl]-decasiloxane; [3-(2-imidazolidino)methyl]-polysiloxane, and [3-(2-imidazolidino)methyl]-polycyclosiloxane.

[0025] In addition, the content of the condensate of compound (1) in the aqueous composition is not particularly limited as long as it is an amount that reacts with multiple hydroxyl groups on the surface of a substrate to enhance adhesion when used as a silane coupling agent, a surface treatment agent, or the like, but from the viewpoint of productivity, it is preferably in the range of 0.0001 to 99 mass%, more preferably 0.01 to 99 mass%, and even more preferably 1 to 99 mass%, based on the aqueous composition.

[0026] The aqueous composition of the present invention may contain water depending on the amount of water added in the production of the aqueous composition described below. Specifically, the alkoxy group of the imidazolidinone silane compound represented by the general formula (2) (hereinafter referred to as "compound (2)") reacts with an equivalent amount of water, so that the aqueous composition contains more than an equivalent amount of water.

[0027] Furthermore, the aqueous composition inevitably contains alcohol generated in response to the alkoxy group of compound (2) during the hydrolysis reaction. Specific examples of alcohols include monohydric alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, sec-propyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, phenol, and benzyl alcohol; and dihydric alcohols such as 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, and 2,3-butanediol.

[0028] From the viewpoint of the environmental load, the content of the alcohol contained in the aqueous composition is less than 5 mass%, preferably 0.0001 to 2.5 mass%, more preferably 0.0001 to 1.5 mass%, and even more preferably 0.0001 to 1.0 mass%, based on the compound (1) and its condensate.

[0029] The method for measuring the contents of compound (1) and its condensate, and the alcohol in the aqueous composition is not particularly limited, and analytical means such as gas chromatography, high performance liquid chromatography, thin layer chromatography, nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), and near infrared spectroscopy (NIR) can be used.

[0030] The aqueous composition of the present invention can be used after diluting with a solvent as long as the effects of the present invention are not impaired. Specific examples of the solvent include ketone solvents such as acetone and methyl isobutyl ketone, ether solvents such as diethyl ether, tetrahydrofuran and dioxane, ester solvents such as ethyl acetate and butyl acetate, and aprotic polar solvents such as acetonitrile and N,N-dimethylformamide, and the like. These solvents may be used alone or in combination of two or more. An acid or base may be used as a pH adjuster.

[0031] The aqueous composition of the present invention can also be purified before use by a method selected from extraction, separation, filtration, recrystallization, distillation, sublimation, chromatography, solid adsorption, and the like, as long as the effects of the present invention are not impaired.

[0032] The aqueous composition of the present invention can also be used as a composition containing one or more other additives selected from pigments, defoamers, lubricants, preservatives, pH adjusters, film formers, antistatic agents, antibacterial agents, surfactants, dyes, and the like, as long as the effects of the present invention are not impaired.

[0033] Next, a method for producing the aqueous composition of the present invention will be described. In the present invention, a hydrolysis reaction is carried out between compound (2) and water, and the generated alcohol is removed to produce an aqueous composition containing compound (1) and its condensate.

[0034] [ka] (In the formula, R 1 , R 2 and n have the same meaning as above.)

[0035] In the general formula (2), R 3 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 3 carbon atoms, and even more preferably 1 or 2 carbon atoms. The monovalent hydrocarbon group may be linear, branched or cyclic, and specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and n-decyl groups; branched alkyl groups such as sec-propyl, sec-butyl, tert-butyl, sec-pentyl, tert-pentyl, sec-hexyl, tert-hexyl, sec-heptyl, tert-heptyl, sec-octyl, tert-octyl, sec-nonyl, tert-nonyl, sec-decyl and tert-decyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, butenyl and methallyl groups; aryl groups such as phenyl, tolyl and xylyl groups; and aralkyl groups such as benzyl and phenethyl groups. Among these, R 3 As the alkyl group, an unsubstituted linear alkyl group having 1 to 6 carbon atoms is preferable, and from the viewpoint of availability in particular, a methyl group or an ethyl group is more preferable.

[0036] In addition, some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted with other substituents, and specific examples of the substituents include alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, and (iso)propoxy groups; halogen atoms such as fluorine, chlorine, and bromine; aromatic hydrocarbon groups such as phenyl groups; cyano groups, amino groups, ester groups, ether groups, carbonyl groups, acyl groups, and sulfide groups, and one or more of these may be used in combination. The substitution positions of these substituents are not particularly limited, and the number of substituents is also not limited.

[0037] Specific examples of the compound (2) include 1-[3-(trimethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)methyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)ethyl]-2-imidazolidinone, and 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone. , 1-[3-(dimethoxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)propyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)butyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)butyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(methoxydi 1-[3-(trimethoxysilyl)hexyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)heptyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)octyl] 1-[3-(dimethoxymethylsilyl)octyl]-2-imidazolidinone, 1-[3-(methoxydimethylsilyl)octyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)methyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)ethyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)ethyl]-2-imidazolidinone,1-[3-(ethoxydimethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)propyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)propyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)butyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)butyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)hexyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)heptyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)heptyl]-2-imidazolidinone 1-[3-(ethoxydimethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)octyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)octyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)octyl]-2-imidazolidinone, 1-[3-(ethoxydimethylsilyl)octyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)methyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)methyl]-2-imidazolidinone Dazolidinone, 1-[3-(tripropoxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)propyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)propyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)butyl]-2-imidazolidinone,1-[3-(dipropoxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)butyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)hexyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3 -(propoxydimethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)heptyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)heptyl]-2-imidazolidinone, 1-[3-(tripropoxysilyl)octyl]-2-imidazolidinone, 1-[3-(dipropoxymethylsilyl)octyl]-2-imidazolidinone, 1-[3-(propoxydimethylsilyl)octyl]-2-imidazolidinone, and the like.

[0038] Among these, from the viewpoint of availability in particular, 1-[3-(trimethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)ethyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)butyl]-2-imidazolidinone, Lisinone, 1-[3-(dimethoxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)pentyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)pentyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)hexyl]-2-imidazolidinone, 1-[3-(dimethoxymethylsilyl)hexyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)methyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)ethyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)propyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)propyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)butyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)butyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)pentyl]-2-imidazolidinone, 1-[3-(diethoxymethylsilyl)pentyl ]-2-imidazolidinone, 1-[3-(triethoxysilyl)hexyl]-2-imidazolidinone, and 1-[3-(diethoxymethylsilyl)hexyl]-2-imidazolidinone are preferred, and 1-[3-(trimethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)ethyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone, 1-[3-(trimethoxysilyl)butyl]-2-imidazolidinone, and 1-[3-(trimethoxysilyl)pentyl]-2-imidazolidinone are preferred.Particularly preferred are 1-[3-(trimethoxysilyl)hexyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)methyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)ethyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)propyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)butyl]-2-imidazolidinone, 1-[3-(triethoxysilyl)pentyl]-2-imidazolidinone, and 1-[3-(triethoxysilyl)hexyl]-2-imidazolidinone.

[0039] The water used in the hydrolysis reaction is not particularly limited as long as it is usable when used as a silane coupling agent, a surface treatment agent, etc., and may be tap water, groundwater, river water, rainwater, natural water, agricultural water, industrial water, purified water, distilled water, ion-exchanged water, pure water, etc. Among these, purified water, distilled water, ion-exchanged water, pure water, etc. are preferred from the viewpoint of having fewer impurities. The amount of water used in the hydrolysis reaction is not particularly limited as long as the hydrolysis reaction proceeds; from the viewpoints of reactivity and productivity, the amount of water used is preferably 3 to 100,000 mol, more preferably 3 to 1,000 mol, and even more preferably 3 to 100 mol, per mol of silicon atom in compound (2).

[0040] The hydrolysis reaction is not particularly limited as long as compound (2) and water are miscible, and may be carried out by either adding compound (2) to water or adding water to compound (2), but from the viewpoint of productivity for smoothly advancing the hydrolysis reaction, the method of adding compound (2) to water is preferred. In addition, examples of the method of adding compound (2) to water include adding compound (2) to water and dropping onto the water surface, and the method of addition or dropping may be either continuous or intermittent.

[0041] The temperature in the hydrolysis reaction is preferably in the range of 0 to 100°C, more preferably 5 to 100°C, and even more preferably 10 to 100°C, from the viewpoints of reactivity and productivity. The time for the hydrolysis reaction is preferably in the range of 0.1 to 30 hours, more preferably 0.5 to 20 hours, and even more preferably 1 to 10 hours, from the viewpoints of reactivity and productivity. From the viewpoints of reactivity and productivity, the pressure in the hydrolysis reaction is preferably in the range of 0.01 to 101.3 kPa, more preferably 0.1 to 101.3 kPa, and even more preferably 1 to 101.3 kPa.

[0042] The hydrolysis reaction proceeds without a solvent, but a solvent can also be used. Examples of the solvent include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene; ketone solvents such as acetone and methyl isobutyl ketone; alcohol solvents such as methyl alcohol and ethyl alcohol; 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 N,N-dimethylformamide; and chlorinated hydrocarbon solvents such as dichloromethane and chloroform. These solvents may be used alone or in combination of two or more. An acid or base may also be used as a pH adjuster. Among these, from the viewpoint of compatibility with compound (2), alcohol-based solvents, ether-based solvents, ester-based solvents, and aprotic polar solvents are particularly preferred.

[0043] The hydrolysis proceeds by the hydrolysis reaction of compound (2) with water, and compound (1) and its condensation product are produced, while alcohol is generated. In the present invention, the alcohol generated by the hydrolysis reaction can be removed during or after the compound (2) and water are mixed. The method for removing the alcohol is not particularly limited, and examples thereof include extraction, separation, filtration, recrystallization, distillation, sublimation, chromatography, chemical conversion, and the like. Among these, distillation is preferred from the viewpoint of productivity.

[0044] The conditions for removing the alcohol by distillation are not particularly limited as long as the conditions allow the volatile alcohol to vaporize. From the viewpoint of productivity, the distillation temperature is preferably in the range of 0 to 300°C, more preferably 5 to 280°C, and even more preferably 10 to 260°C. From the viewpoint of productivity, the distillation time is preferably in the range of 1 to 50 hours, more preferably 1 to 30 hours, and even more preferably 1 to 10 hours. From the viewpoint of productivity, the distillation pressure is preferably in the range of 0.01 to 101.3 kPa, more preferably 0.1 to 101.3 kPa, and even more preferably 1 to 101.3 kPa.

[0045] In the production method of the present invention, the generated alcohol can be removed until the content of the generated alcohol in compound (1) and its condensate becomes less than 5 mass %, so that the environmental load can be significantly reduced when the obtained aqueous composition is used as a silane coupling agent, a surface treatment agent, etc.

[0046] By carrying out a silane coupling treatment or surface treatment of a substrate using the aqueous composition of the present invention, the adhesion of the treated organic-inorganic composite material can be improved. The method for treating a substrate using the aqueous composition of the present invention will be described below. The method of treating a substrate using the aqueous composition of the present invention is not particularly limited, and examples thereof include a method of applying the aqueous composition to the substrate, a method of entraining the aqueous composition with an inert gas and contacting the substrate with the entrained gas, a method of directly mixing the aqueous composition with the substrate in a mixer or mill, etc. Among these, the method of applying the aqueous composition is preferred from the viewpoint of simplicity. Examples of methods for applying the aqueous composition include brush coating, spray coating, wire bar coating, blade coating, roll coating, and dipping.

[0047] The conditions under which the aqueous composition of the present invention is applied to, contacted with, or mixed with a substrate for treatment are not particularly limited, so long as the conditions are such that the silanol groups react with the hydroxyl groups on the surface of the substrate. From the viewpoint of productivity, the treatment temperature is preferably in the range of 0 to 100°C, more preferably 10 to 50°C, and even more preferably 20 to 30°C. From the viewpoint of productivity, the treatment time is preferably in the range of 1 minute to 10 hours, more preferably 1 minute to 5 hours, and even more preferably 1 minute to 2 hours, but may be appropriately set in relation to the above treatment temperature.

[0048] The substrate to be treated may be either an inorganic or an organic material. Examples of inorganic materials include silicon compounds such as glass plate, glass fiber, diatomaceous earth, calcium silicate, silica, silicon, talc, and mica, metal oxides such as zinc oxide, aluminum oxide, tin oxide, titanium oxide, iron oxide, and magnesium oxide, metal chlorides such as zinc chloride, aluminum chloride, tin chloride, titanium chloride, iron chloride, and magnesium chloride, metal hydroxides such as aluminum hydroxide and magnesium hydroxide, and carbonates such as calcium carbonate, zinc carbonate, and magnesium carbonate. Among these, silicon compounds and metal oxides are particularly preferred from the viewpoint of reactivity with the silanol groups of the imidazolidinone silane compound. Examples of organic materials include natural polymers such as rubber, paper, and cellulose; synthetic polymers such as acrylic resins, urethane resins, epoxy resins, and phenolic resins; oils and fats, surfactants, liquid crystals, etc. Among these, natural polymers and synthetic polymers are particularly preferred from the viewpoint of reactivity with the imidazolidinone group of the imidazolidinone silane compound.

[0049] After the substrate is treated with the aqueous composition of the present invention, excess aqueous composition is removed by washing, drying, etc. The post-treatments by washing and drying may be performed alone or in combination. The washing solvent is not particularly limited, but water or the same solvents as those exemplified as the solvent for diluting the above-mentioned aqueous composition can be used. The cleaning method is not particularly limited, but may be, for example, a method in which the treated substrate is immersed in a cleaning solvent or a method in which the cleaning solvent is sprayed on the substrate. The conditions for washing and drying are not particularly limited as long as they do not adversely affect the substrate after treatment. The washing temperature is preferably in the range of 0 to 300°C, more preferably 0 to 200°C, and even more preferably 0 to 100°C, from the viewpoint of productivity. From the viewpoint of productivity, the washing time is preferably in the range of 1 minute to 10 hours, more preferably 1 minute to 5 hours, and even more preferably 1 minute to 2 hours, and may be appropriately set in relation to the above washing temperature. From the viewpoint of productivity, the drying temperature is preferably in the range of 0 to 300°C, more preferably 0 to 200°C, and even more preferably 0 to 100°C. From the viewpoint of productivity, the drying time is preferably in the range of 1 minute to 10 hours, more preferably 1 minute to 5 hours, and even more preferably 1 minute to 2 hours, and may be appropriately set in relation to the above drying temperature. EXAMPLES

[0050] The present invention will be described in more detail below with reference to examples, comparative examples and application examples, but the present invention is not limited to the following examples. The residual alcohol content was measured by gas chromatography under the following conditions: The non-volatile content was measured by the heat residue method after heating and drying at 105°C for 3 hours on an aluminum petri dish. [Gas chromatography measurement conditions] Gas chromatograph: GC-2014 (Shimadzu Corporation) Packed column: Silicone SE-30 (GL Sciences, Inc.) Detector:TCD Detector temperature: 300℃ Inlet temperature: 300℃ Heating program: 70℃ (0 min) → 10℃ / min → 300℃ (10 min) Carrier gas: Helium (50ml / min) Injection volume: 1μl

[0051] [1] Preparation of an aqueous composition containing compound (1) and its condensate [Example 1] Preparation of an aqueous composition containing 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its condensate In a flask equipped with a stirrer, a reflux condenser, a Dean Stark, a dropping funnel and a thermometer, 54.0g (3,000 mol) of pure water was charged at room temperature and heated to 60°C. After the internal temperature stabilized, 24.8g (0.100 mol) of 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone was added dropwise over 5 hours. After stirring at 60°C for 1 hour under normal pressure, the generated methanol was extracted while heating, and when the column top temperature reached 100°C, heating was stopped. After cooling to room temperature, pure water was added so that the nonvolatile content was 25 to 26% by mass, and a colorless and transparent aqueous composition was prepared. The aqueous composition thus prepared was analyzed by gas chromatography (internal standard method), and it was confirmed that the area % ratio of residual methanol to silanol compound (total of 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its silanol condensate) was 0.3:99.7. In addition, when the composition was dried by heating in a hot air oven at 105°C for 3 hours, the non-volatile content was 25% by mass.

[0052] Even if this aqueous composition is left at room temperature for more than one month, no further methanol is generated, no insoluble high molecular weight substances are generated, and it remains colorless and transparent, and can be stored in a chemically stable state. Even if it is diluted 25 times with pure water, no further methanol is generated. The diluted aqueous composition can also be stored in a chemically stable state for more than one month.

[0053] [Example 2] Preparation of an aqueous composition containing 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its condensate A hydrolysis reaction was carried out in the same manner as in Example 1, except that the amount of pure water used was changed to 540.0 g (30,000 mol), and then methanol was extracted. After cooling to room temperature, pure water was added so that the non-volatile content was 1 to 2 mass %, and a colorless and transparent aqueous composition was prepared. The aqueous composition thus prepared was analyzed by gas chromatography (internal standard method), and it was confirmed that the area % ratio of the residual methanol to the silanol compound (the total of 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its silanol condensate) was 0.2:99.8. In addition, when the composition was dried by heating in a hot air oven at 105°C for 3 hours, the non-volatile content was 1 mass%.

[0054] Even when this aqueous composition was left at room temperature for more than one month, no further methanol was generated, no insoluble high molecular weight substances were generated, and the composition remained colorless and transparent, and could be stored in a chemically stable state. Furthermore, even when the composition was diluted 25 times with pure water, no additional methanol was generated. The diluted aqueous composition could also be stored in a chemically stable state for more than one month.

[0055] [Example 3] Preparation of an aqueous composition containing 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its condensate A hydrolysis reaction was carried out in the same manner as in Example 1, except that 29.0 g (0.100 mol) of 1-[3-(triethoxysilyl)propyl]-2-imidazolidinone was used instead of 1-[3-(triethoxysilyl)propyl]-2-imidazolidinone in Example 1, and then ethanol was extracted. After cooling to room temperature, pure water was added so that the nonvolatile content was 25 to 26 mass %, and a colorless and transparent aqueous composition was prepared. The aqueous composition thus prepared was analyzed by gas chromatography (internal standard method), and it was confirmed that the area percentage ratio of the residual ethanol to the silanol compound (the total of 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its silanol condensate) was 0.4:99.6. In addition, when the composition was dried by heating in a hot air oven at 105°C for 3 hours, the non-volatile content was 25% by mass.

[0056] Even if this aqueous composition is left at room temperature for more than one month, no further ethanol is generated, no insoluble high molecular weight substances are generated, and it remains colorless and transparent, and can be stored in a chemically stable state. Even if it is diluted 25 times with pure water, no further ethanol is generated. The diluted aqueous composition can also be stored in a chemically stable state for more than one month.

[0057] [Example 4] Preparation of an aqueous composition containing 1-[3-(dihydroxymethylsilyl)propyl]-2-imidazolidinone and its condensate A hydrolysis reaction was carried out in the same manner as in Example 1, except that 23.2 g (0.100 mol) of 1-[3-(dimethoxymethylsilyl)propyl]-2-imidazolidinone was used instead of 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone in Example 1, and then methanol was extracted. After cooling to room temperature, pure water was added so that the nonvolatile content was 25 to 26 mass %, and a colorless and transparent aqueous composition was prepared. The aqueous composition thus prepared was analyzed by gas chromatography (internal standard method), and it was confirmed that the area % ratio of the residual methanol to the silanol compound (the total of 1-[3-(dihydroxymethylsilyl)propyl]-2-imidazolidinone and its silanol condensate) was 0.3:99.7. In addition, when the composition was dried by heating in a hot air oven at 105°C for 3 hours, the non-volatile content was 25% by mass.

[0058] Even if this aqueous composition is left at room temperature for more than one month, no further methanol is generated, no insoluble high molecular weight substances are generated, and it remains colorless and transparent, and can be stored in a chemically stable state. Even if it is diluted 25 times with pure water, no further methanol is generated. The diluted aqueous composition can also be stored in a chemically stable state for more than one month.

[0059] [2] Preparation of an aqueous composition containing a silanol compound having an organic group other than an imidazolidinone group and a silanol condensate Comparative Example 1 Preparation of an aqueous composition containing 3-(trihydroxysilyl)propylamine and its condensate Hydrolysis was carried out in the same manner as in Example 1, except that 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone in Example 1 was changed to 17.9 g (1.000 mol) of 3-(trimethoxysilyl)propylamine, and then methanol was removed. During removal of methanol, the appearance of the aqueous composition turned yellow.

[0060] Comparative Example 2 Preparation of an aqueous composition containing 3-(trihydroxysilyl)propylethylenediamine and its condensate Hydrolysis was carried out in the same manner as in Example 1, except that 22.2 g (0.100 mol) of 3-(trimethoxysilyl)propylethylenediamine was used instead of 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone in Example 1, and then methanol was removed. During removal of methanol, the appearance of the aqueous composition turned yellow.

[0061] Comparative Example 3 Preparation of an aqueous composition containing 3-(trihydroxysilyl)propylphenylamine and its condensate Hydrolysis was carried out in the same manner as in Example 1, except that 25.5 g (0.100 mol) of 3-(trimethoxysilyl)propylphenylamine was used instead of 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone in Example 1, and then methanol was removed. During removal of methanol, a solid high molecular weight substance having low compatibility with the aqueous composition was produced.

[0062] Comparative Example 4 Preparation of an aqueous composition containing 3-(trihydroxysilyl)propane and its condensate Except for changing the 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone in Example 1 to 16.4 g (0.100 mol) of 3-(trimethoxysilyl)propane and using THF as the solvent, hydrolysis was performed in the same manner as in Example 1, and then methanol was extracted. During the extraction of methanol, a solid high molecular weight substance having low compatibility with the aqueous composition was produced.

[0063] Comparative Example 5 Preparation of an aqueous composition containing 3-(trihydroxysilyl)propyl methacrylate and its condensate Except for changing 1-[3-(trimethoxysilyl)propyl]-2-imidazolidinone in Example 1 to 24.8 g (0.100 mol) of 3-(trimethoxysilyl)propyl methacrylate and using THF as the solvent, hydrolysis was performed in the same manner as in Example 1, and then methanol was removed. During removal of methanol, a solid high molecular weight substance having low compatibility with the aqueous composition was produced.

[0064] [3] Treatment of a substrate with an aqueous composition containing compound (1) and its condensate [Application Example 1] Treatment of a substrate with an aqueous composition containing 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its condensate Pure water was added to the aqueous composition containing 1-[3-(trihydroxysilyl)propyl]-2-imidazolidinone and its condensate obtained in Example 1 so that the non-volatile content was 1% by mass, and the concentration was adjusted. A glass plate (manufactured by Matsunami Glass Industry Co., Ltd.; slide glass, white-green polished frost No. 1, size 76 mm x 26 mm, thickness 0.8 to 1.0 mm, frost width 15 mm x 26 mm) previously cleaned with UV ozone was immersed in 100 mL of the aqueous composition adjusted to 1% by mass at 25°C for 1 hour for treatment. The glass plate was removed from the aqueous composition, immersed in 100 mL of acetone, and ultrasonically cleaned at 25°C for 1 hour using an ultrasonic cleaner (manufactured by Honda Electronics Co., Ltd.; W-221), and then dried at 50°C for 1 hour.

[0065] After drying, the contact angle of pure water (1 μL) was measured at 10 random locations on the treated surface of the glass plate at 25°C and 50% RH using a contact angle meter (DMs-401, analysis software FAMAS) manufactured by Kyowa Interface Science Co., Ltd. The average contact angle was 32°, with a standard deviation of less than 1.8°. This indicates that the silanol groups form covalent bonds with the hydroxyl groups on the glass plate surface, and the introduction of imidazolidinone groups makes the treated surface hydrophilic.

[0066] [Application Example 2] Treatment of a substrate with an aqueous composition containing 1-[3-(dihydroxymethylsilyl)propyl]-2-imidazolidinone and its condensate A glass plate was treated in the same manner as in Application Example 1, except that the aqueous composition containing 1-[3-(dihydroxymethylsilyl)propyl]-2-imidazolidinone obtained in Example 4 and its condensate was used. When the contact angle of the dried glass plate was measured in the same manner as in Application Example 1, the average contact angle was 32° with a standard deviation of less than 1.8°. This indicates that the silanol groups form covalent bonds with the hydroxyl groups on the glass plate surface, introducing imidazolidinone groups, which makes the treated surface hydrophilic.

Claims

1. The following general formula (1) 【Chemistry 1】 (In the formula, R 1 represents a halogen atom or a methyl group, R 2 represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms, and n represents an integer of 0 or 1. and a condensate of the silanol compound, The colorless and transparent aqueous composition has an alcohol content of less than 5 mass % based on the silanol compound and the condensate of the silanol compound.

2. The following general formula (2) 【Chemistry 2】 (In the formula, R 1 , R 2 and n are as defined above, R 3 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms.

2. A method for producing the aqueous composition according to claim 1, comprising the steps of hydrolyzing an imidazolidinone silane compound represented by the following formula (I) in the presence of water and removing the generated alcohol.

3. 3. The method for producing an aqueous composition according to claim 2, wherein the amount of the water is 3 to 100,000 moles per mole of silicon atom of the imidazolidinone silane compound.

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