Hydrocarbon terminal group-containing compound, surface treatment agent, article, and film forming method

Abstract

Using a non-fluorine-based hydrocarbon terminal group-containing compound that has at least one linear, branched, or cyclic C3-60 monovalent hydrocarbon terminal group and that further has at least one reactive silazane group makes it possible for a surface treatment agent containing said compound to form, in a short time, a cured film that has rapid curability and that exhibits excellent water repellency, excellent slipperiness, an excellent strain removal property, and excellent abrasion resistance, particularly steel wool abrasion resistance.

Description

Hydrocarbon end group-containing compound, surface treatment agent and article, and coating film formation method

[0001] The present invention relates to a hydrocarbon terminal group-containing compound, and more particularly to a non-fluorinated hydrocarbon terminal group-containing compound, particularly an alkyl terminal group-containing compound, which has fast curing properties and is capable of forming a coating film having excellent water repellency and abrasion resistance; a surface treatment agent containing the compound; an article surface-treated with the surface treatment agent; and a coating formation method in which the surface treatment agent is applied to a substrate.

[0002] In recent years, the use of touch panels in displays, such as smartphones and in-vehicle displays, has accelerated. However, touch panels have exposed screens, which are often directly touched by fingers or cheeks, making them susceptible to sebum and other contaminants. Therefore, there is an increasing demand for technologies that make display surfaces less susceptible to fingerprints and easier to clean, thereby improving appearance and visibility. The development of materials that can meet these demands is highly desirable. Touch panel display surfaces are particularly susceptible to fingerprints, making them ideal for providing a water- and oil-repellent layer. However, while conventional water- and oil-repellent layers offer high water- and oil-repellent properties and excellent wipeability, they lack sufficient abrasion resistance and are prone to fingerprints being easily visible.

[0003] In general, fluoropolyether group-containing compounds have very low surface free energy and therefore have water and oil repellency, chemical resistance, lubricity, release properties, antifouling properties, etc. Utilizing these properties, they are widely used industrially as water and oil repellent and antifouling agents for paper and textiles, lubricants for magnetic recording media, oil repellents for precision instruments, release agents, cosmetics, protective films, etc. However, these properties also mean that they are non-sticky and non-adhesive to other substrates, and even if they can be applied to the surface of a substrate, it has been difficult to adhere the coating to it.

[0004] Silane coupling agents are well known for bonding organic compounds to the surface of substrates such as glass and cloth, and are widely used as coating agents for various substrate surfaces. Silane coupling agents contain an organic functional group and a reactive silyl group (generally a hydrolyzable silyl group such as an alkoxysilyl group) in one molecule. The hydrolyzable silyl group undergoes a self-condensation reaction in the presence of moisture in the air to form a coating. The hydrolyzable silyl group chemically and physically bonds with the surface of glass, metal, or the like, resulting in a durable, strong coating.

[0005] Thus, compositions have been disclosed that use fluoropolyether group-containing polymers in which hydrolyzable silyl groups have been introduced into fluoropolyether group-containing compounds, which can form coatings that easily adhere to substrate surfaces and have water and oil repellency, chemical resistance, lubricity, releasability, antifouling properties, and the like on the substrate surfaces (Patent Documents 1 to 6: JP-T-2008-534696A, JP-T-2008-537557A, JP-A-2012-072272A, JP-A-2012-157856A, JP-A-2013-136833A, and JP-A-2015-199906A).

[0006] However, fluorine-containing compounds such as fluoropolyether group-containing compounds are characterized by their resistance to decomposition in nature and tend to accumulate in nature, which has led to a demand for the development of surface protective agents for non-fluorine-containing materials.

[0007] Furthermore, there has been a demand for surface protective agents for non-fluorine-based materials that are easy to work with and that cure in a relatively short time, comparable to the fluoropolyether group-containing compounds that have alkoxysilyl groups as hydrolyzable silyl groups that have been used up to now.

[0008] Japanese Patent Publication No. 2008-534696 Japanese Patent Publication No. 2008-537557 Japanese Patent Publication No. 2012-072272 Japanese Patent Publication No. 2012-157856 Japanese Patent Publication No. 2013-136833 Japanese Patent Publication No. 2015-199906

[0009] The present invention has been made in view of the above circumstances, and aims to provide a fast-curing, non-fluorine-based (i.e., having no fluorine atoms in the molecule) hydrocarbon terminal group-containing compound that can form a cured coating that is excellent in water repellency, slipperiness, dirt wipeability, and abrasion resistance; a substantially fluorine-free surface treatment agent that contains the compound; an article that has been surface-treated with the surface treatment agent; and a coating formation method that involves applying the surface treatment agent to a substrate.

[0010] As a result of intensive research conducted by the present inventors to achieve the above object, they have found that by using a non-fluorine-based hydrocarbon terminal group-containing compound having at least one linear, branched or cyclic monovalent hydrocarbon terminal group having 3 to 60 carbon atoms and further having at least one reactive silazane group as a surface protective agent for the above non-fluorine-based material, a surface treatment agent containing the compound has fast curing properties and can form, in a short period of time, a cured coating that is excellent in water repellency, slipperiness, dirt wiping ability and abrasion resistance, particularly steel wool abrasion resistance, and has thereby completed the present invention.

[0011] Accordingly, the present invention provides the following hydrocarbon terminal group-containing compound, surface treatment agent and article, and coating film forming method. [1] A non-fluorine-based hydrocarbon terminal group-containing compound having at least one linear, branched, or cyclic monovalent hydrocarbon terminal group having 3 to 60 carbon atoms and further having at least one reactive silazane group. [2] The hydrocarbon terminal group-containing compound according to [1], wherein the hydrocarbon terminal group is a group selected from an alkyl group having 6 to 28 carbon atoms and an aryl group having 6 to 32 carbon atoms. [3] The hydrocarbon terminal group-containing compound according to [1] or [2], which has two or more hydrocarbon terminal groups and has a trivalent or higher linking group between the hydrocarbon terminal group and the reactive silazane group. [4] The hydrocarbon terminal group-containing compound is a compound represented by the following general formula (1): (In the formula, R 1 are monovalent hydrocarbon groups having 3 to 32 carbon atoms, which may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which may be linear, branched, or cyclic, or a combination thereof; R 2represents a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group; V independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom; Z independently represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group; Y independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom; and A independently represents a group represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, n" is a number from 0 to 3, n'" is an integer from 0 to 2, the sum of n" and n'" is a number of 3 or less, and n' is (3-(n"+n'")) / 2), k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is 1 or 2, k1+k2+k3 is 2, 3, or 4, and m is an integer from 1 to 7. [5] A hydrocarbon terminal group-containing compound according to [1], represented by the following formula (1): 1 is a monovalent hydrocarbon group having 13 to 32 carbon atoms, which may be linear, branched, or cyclic, or a combination thereof. [6] The hydrocarbon terminal group-containing compound according to [4] or [5], wherein k1 in formula (1) is 2 or 3. [7] The hydrocarbon terminal group-containing compound according to formula (1), wherein R 1 But the following formula (In the formula, R Arepresents a monovalent hydrocarbon group having 3 to 32 carbon atoms, which may be linear, branched, or cyclic, or a combination thereof; Q independently represents an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, a carbonyl (ketone) group, an ester group, a carbonate group, a sulfinyl group, a sulfonyl group, a thioester group, a thiocarbonate group, a thiocarbamate group, an amino group, an amide group, or a carbamate group. , a urea group, and a divalent nitrogen-containing heterocyclic group; Q' are independently a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, and a trivalent nitrogen-containing heterocyclic group; Q" are independently a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, and a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent organopolysiloxane residue having 3 to 10 silicon atoms; R B are independently a single bond or a divalent hydrocarbon group having 1 to 32 carbon atoms, which may be linear, branched, or cyclic; R C are independently R Aor a hydrogen atom, and p is an integer of 0 to 10. However, the total number of carbon atoms in each structure is 32 or less. [8] The hydrocarbon terminal group-containing compound according to any one of [4] to [7], wherein in the formula (1), Y is selected from the group consisting of an alkylene group having 1 to 20 carbon atoms which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms, an alkylene group having 1 to 10 carbon atoms including an arylene group having 6 to 8 carbon atoms, a divalent group in which alkylene groups having 1 to 8 carbon atoms are bonded to each other via a diorganosilylene group, a silalkylene structure, a silarylene structure, or a nitrogen-containing heterocyclic group, and a divalent group in which an alkylene group having 1 to 10 carbon atoms is bonded to a bond of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms. [9] The hydrocarbon terminal group-containing compound according to the formula (1), wherein Z is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, -SiR 3 = (R 3 represents a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), 4 = (R 4represents a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms), a trivalent to octavalent group selected from the group consisting of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent to octavalent nitrogen-containing heterocycle-containing group.

[10] The hydrocarbon terminal group-containing compound according to any one of [4] to [9], wherein in the above formula (1), U is a trivalent or tetravalent group selected from the group consisting of a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear trivalent or tetravalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent or tetravalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent or tetravalent nitrogen-containing heterocyclic group.

[11] A surface treatment agent comprising the hydrocarbon terminal group-containing compound according to any one of [1] to

[10] and / or a partial hydrolysis condensate thereof.

[12] An article surface-treated with the surface treatment agent according to

[11] .

[13] A method for forming a coating by applying a surface treatment agent to a substrate, wherein the surface treatment agent contains a non-fluorine-based hydrocarbon terminal group-containing compound and / or a partial hydrolysis condensate thereof, which has at least one linear, branched, or cyclic monovalent hydrocarbon terminal group having 3 to 60 carbon atoms and further has at least one reactive silazane group.

[14] The method for forming a coating according to

[13] , wherein the hydrocarbon terminal group of the hydrocarbon terminal group-containing compound is a group selected from an alkyl group having 6 to 28 carbon atoms and an aryl group having 6 to 32 carbon atoms.

[15] The method for forming a coating according to

[13] or

[14] , wherein the hydrocarbon terminal group-containing compound has two or more hydrocarbon terminal groups and a trivalent or higher linking group between the hydrocarbon terminal group and the reactive silazane group.

[16] The method for forming a coating according to

[13] or

[14] , wherein the hydrocarbon terminal group-containing compound is a compound represented by the following general formula (1): (In the formula, R 1are monovalent hydrocarbon groups having 3 to 32 carbon atoms, which may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which may be linear, branched, or cyclic, or a combination thereof; R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group; V independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom; Z independently represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group; Y independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom; and A independently represents a group represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, n" is a number from 0 to 3, n'" is an integer from 0 to 2, the sum of n" and n'" is a number of 3 or less, and n' is (3-(n"+n'")) / 2), k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is 1 or 2, k1+k2+k3 is 2, 3 or 4, and m is an integer from 1 to 7.) The method for forming a coating according to any one of

[13] to

[15] , wherein the coating on the surface of the substrate has a water contact angle of 90° or more 30 minutes after application of the surface treatment agent.

[0012] The hydrocarbon terminal group-containing compound of the present invention has excellent fast curing properties, and articles surface-treated with a surface treatment agent containing this compound have excellent water repellency, slipperiness, dirt wiping properties, and abrasion resistance, despite being non-fluorine-based.

[0013] The hydrocarbon terminal group-containing compound of the present invention is characterized by being a non-fluorine-based compound having at least one linear, branched or cyclic monovalent hydrocarbon terminal group (also referred to as a hydrocarbon chain terminal group) having 3 to 60 carbon atoms and further having at least one reactive silazane group.

[0014] The hydrocarbon terminal group-containing compound of the present invention has at least one hydrocarbon chain terminal group with a predetermined carbon number, which improves its molecular mobility (flexibility of the compound structure including the hydrocarbon chain). This allows the cured coating of a surface treatment agent containing the compound to exhibit water repellency and excellent slip properties, dirt wiping properties, and abrasion resistance. Furthermore, the presence of at least one reactive silazane group provides strong adhesion to the substrate and improved abrasion resistance. Furthermore, the hydrolysis rate is improved, allowing for faster adhesion to the substrate, thereby accelerating the development of water repellency. In other words, the surface treatment agent containing the compound exhibits excellent rapid curing properties.

[0015] In the present invention, "rapid curing" refers to the speed at which the surface properties of a coating of a surface treatment agent applied to a substrate are developed (for example, the speed at which water repellency is developed during film formation), and "having rapid curing properties" refers to the surface properties of a coating of a surface treatment agent applied to a substrate being developed in a short period of time. In the examples described below, the water contact angle of the coating on the substrate surface 30 minutes after application of the surface treatment agent was evaluated, and those with a good water contact angle (90° or more) were deemed to have "rapid curing properties."

[0016] In the hydrocarbon terminal group-containing compound (organosilane compound) of the present invention, the hydrocarbon chain terminal group is a linear, branched, or cyclic monovalent hydrocarbon group having 3 to 60 carbon atoms, preferably a group selected from an alkyl group having 6 to 28 carbon atoms and an aryl group having 6 to 32 carbon atoms, and more preferably an alkyl group having 10 to 28 carbon atoms. The hydrocarbon chain terminal group preferably has two or more hydrocarbon chain terminal groups with a predetermined number of carbon atoms, more preferably two or three. Furthermore, it is preferable for a linking group to be present between the hydrocarbon terminal group and the reactive silazane group. When a linking group is present, the linking group is preferably trivalent or higher, more preferably trivalent or tetravalent. The term "linking group" refers to a group excluding the hydrocarbon terminal group and the reactive silazane group.

[0017] The hydrocarbon terminal group-containing compound of the present invention is preferably represented by the following general formula (1). (In the formula, R 1are monovalent hydrocarbon groups having 3 to 32 carbon atoms, which may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which may be linear, branched, or cyclic, or a combination thereof; R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group; V independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom; Z independently represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group; Y independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom; and A independently represents a group represented by the following general formula (2): (In the formula, R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, n" is a number from 0 to 3, n'" is an integer from 0 to 2, the sum of n" and n'" is a number of 3 or less, and n' is (3-(n"+n'")) / 2), k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is 1 or 2, k1+k2+k3 is 2, 3, or 4, and m is an integer from 1 to 7.)

[0018] In the above formula (1), R 1are monovalent hydrocarbon groups having 3 to 32 carbon atoms, preferably 6 to 28 carbon atoms, and more preferably 8 to 28 carbon atoms, which may independently contain at least one atom selected from oxygen atoms, sulfur atoms, nitrogen atoms, and silicon atoms, and which may be linear, branched, or cyclic, or a combination thereof. When at least one atom selected from oxygen atoms, sulfur atoms, nitrogen atoms, and silicon atoms is contained, it is preferable that it be contained as a group such as an ether group, carbonyl (ketone) group, ester group, carbonate group, thioether group, sulfinyl group, sulfonyl group, thioester group, thiocarbonate group, thiocarbamate group, amino group, amide group, carbamate group, urea group, oxazole group, imidazole group, triazole group, cyanurate group, isocyanurate group, diorganosilylene group, organopolysiloxane residue, silalkylene group, or silarylene group.

[0019] R 1 is preferably a group represented by the following formula: (In the formula, R Arepresents a monovalent hydrocarbon group having 3 to 32 carbon atoms which may be linear, branched, or cyclic, or a combination thereof; Q independently represents an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, a carbonyl (ketone) group, an ester group, a carbonate group, a sulfinyl group, a sulfonyl group, a thioester group, a thiocarbonate group, a thiocarbamate group, an amino group, an amide group, a carbamate group, a urea group, a divalent nitrogen-containing heterocyclic group (a divalent oxazole group, a divalent imidazole group, a divalent benzoyl ... Q' is independently a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, and a trivalent nitrogen-containing heterocyclic group (a trivalent cyanurate group, a trivalent isocyanurate group, a trivalent triazole group, etc.), Q" is independently a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, and a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic tetravalent organopolysiloxane residue having 3 to 10 silicon atoms, R B are independently a single bond or a divalent hydrocarbon group having 1 to 32 carbon atoms, which may be linear, branched, or cyclic; R C are independently R A or a hydrogen atom, and p is an integer of 0 to 10. However, the total number of carbon atoms in each structure is 32 or less.

[0020] In the above formula, R A R is a monovalent hydrocarbon group having 3 to 32 carbon atoms, preferably 6 to 28 carbon atoms, and more preferably 8 to 28 carbon atoms, which may be linear, branched, or cyclic, or a combination thereof. A Examples of such materials include the following: (In the formula, x is an integer of 2 to 31, preferably 5 to 27, and more preferably 7 to 27, and y and y' are each an integer of 1 or more such that the total number of carbon atoms in each structure is 32 or less.)

[0021] In the above formula, Q independently represents a divalent group selected from the group consisting of an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear divalent organopolysiloxane residue having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or a branched or cyclic divalent organopolysiloxane residue having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms, a carbonyl (ketone) group, an ester group, a carbonate group, a sulfinyl group, a sulfonyl group, a thioester group, a thiocarbonate group, a thiocarbamate group, an amino group, an amide group, a carbamate group, a urea group, and a divalent nitrogen-containing heterocyclic group (such as a divalent oxazole group, a divalent imidazole group, or a divalent triazole group).

[0022] Here, the group bonded to a silicon atom in a diorganosilylene group, a silalkylene structure, a silarylene structure, or an organopolysiloxane residue is preferably an alkyl group having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, such as a methyl group, an ethyl group, a propyl group, or a butyl group, or a phenyl group. Furthermore, the alkylene group in the silalkylene structure is preferably an ethylene group, a propylene group (trimethylene group, methylethylene group), a butylene group (tetramethylene group, methylpropylene group), or the like, having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Furthermore, the organopolysiloxane residue may contain a silalkylene structure in which two silicon atoms are bonded via an alkylene group, such as an ethylene group or a propylene group.

[0023] Examples of such Q include the following: In the following structure, when the bond on the left side is R A or R B and the bond on the right is R B and combine. (In the formula, f is an integer of 2 to 4, and e is an integer of 1 to 9.)

[0024] In the above formula, Q' independently represents a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or a branched or cyclic trivalent organopolysiloxane residue having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms, a trivalent amide group, and a trivalent nitrogen-containing heterocyclic group (such as a trivalent cyanurate group, a trivalent isocyanurate group, or a trivalent triazole group).

[0025] The organopolysiloxane residue preferably contains a phenyl group or an alkyl group such as a methyl group, ethyl group, propyl group, or butyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The organopolysiloxane residue may also contain a silalkylene structure in which two silicon atoms are bonded via an alkylene group such as an ethylene group or a propylene group.

[0026] Examples of such Q' include the following: In the following structure, the bond on the left side is R A or R B and the bond on the right is R B and the other bonds are R C and combine. (wherein f is an integer of 2 to 4.)

[0027] In the above formula, Q" is independently a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, and a linear tetravalent organopolysiloxane residue having 2 to 10 silicon atoms, and particularly 2 to 8 silicon atoms, or a branched or cyclic tetravalent organopolysiloxane residue having 3 to 10 silicon atoms, and particularly 3 to 8 silicon atoms.

[0028] The organopolysiloxane residue preferably contains a phenyl group or an alkyl group such as a methyl group, ethyl group, propyl group, or butyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The organopolysiloxane residue may also contain a silalkylene structure in which two silicon atoms are bonded via an alkylene group such as an ethylene group or a propylene group.

[0029] Examples of such Q" include the following: In the following structure, the bond on the left is R A or R B and the bond on the right is R B and the other bonds are R C and combine.

[0030] In the above formula, R B are independently a single bond or a divalent hydrocarbon group having 1 to 32 carbon atoms which may be linear, branched or cyclic, and examples thereof include the following: (In the formula, z is an integer from 1 to 12.)

[0031] In the above formula, R C are independently R A or a hydrogen atom. C is R A When R A may be the same as or different from.

[0032] In the above formula, p is an integer of 0 to 10, and is preferably 0, 1, or 2. However, R 1 The total number of carbon atoms in each structure is 32 or less.

[0033] Such an R 1 As the solvent, the following are preferably used. (In the formula, x, y, y', and z are the same as above, with the proviso that the total number of carbon atoms in each structure is 3 to 32.)

[0034] In the above formula (1), R 2 R is a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms (a methyl group, an ethyl group). 2is preferably a hydrogen atom, a chlorine atom, a hydroxyl group, a methyl group, or an ethyl group.

[0035] In the above formula (1), U represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group. The trivalent or tetravalent organic group is preferably a trivalent or tetravalent group selected from a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear organopolysiloxane residue having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent or tetravalent nitrogen-containing heterocyclic group (such as a trivalent cyanurate group, a trivalent isocyanurate group, or a trivalent triazine ring-containing group).

[0036] The organopolysiloxane residue preferably contains a phenyl group or an alkyl group such as a methyl group, ethyl group, propyl group, or butyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The organopolysiloxane residue may also contain a silalkylene structure in which two silicon atoms are bonded via an alkylene group such as an ethylene group or a propylene group.

[0037] Examples of such U include the following: In the following structure, it is preferable that the bond on the right side is bonded to V.

[0038] In the above formula (1), V is independently a single bond or a divalent hydrocarbon group having 1 to 20 carbon atoms which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom, and is a linking group connecting the U group and the Z group. When Z is a single bond, V is preferably a single bond. Specific examples of the divalent hydrocarbon group include an alkylene group having 1 to 10 carbon atoms which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom, and an alkylene group having 1 to 10 carbon atoms including an arylene group having 6 to 8 carbon atoms (for example, an alkylene / arylene group having 7 to 18 carbon atoms).

[0039] Specific examples of such V include the following, in addition to a single bond: In the following structure, the left bond is bonded to U, and the right bond is bonded to Z. (In the formula, q is an integer of 1 to 10, r, s, and t are each an integer of 1 to 8, the sum of r and s is an integer of 2 to 10, and the sum of r, s, and t is an integer of 3 to 10.)

[0040] In the above formula (1), Z independently represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group. The trivalent to octavalent organic group is a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, -SiR 3 = (R 3 represents a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), 4 = (R 4 represents a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms); a linear organopolysiloxane residue having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms; a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent to octavalent nitrogen-containing heterocycle-containing group (such as a trivalent cyanurate group, a trivalent isocyanurate group, or a trivalent or tetravalent triazine ring-containing group).

[0041] The organopolysiloxane residue preferably contains a phenyl group or an alkyl group such as a methyl group, ethyl group, propyl group, or butyl group having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. The organopolysiloxane residue may also contain a silalkylene structure in which two silicon atoms are bonded via an alkylene group such as an ethylene group or a propylene group.

[0042] Examples of such Z include the following, in addition to a single bond: In the following structure, the bond on the left side is bonded to V, and the other bond is bonded to Y. (wherein f is an integer of 2 to 4.)

[0043] In the above formula (1), Y is independently a single bond or a divalent hydrocarbon group having 1 to 20 carbon atoms which may contain at least one atom selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom, and is a linking group connecting the Z group and the A group. Specific examples of the divalent hydrocarbon group include alkylene groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms; alkylene groups having 1 to 10 carbon atoms including an arylene group having 6 to 8 carbon atoms (for example, an alkylene-arylene group having 7 to 18 carbon atoms); divalent groups in which alkylene groups having 1 to 8 carbon atoms are bonded to each other via a diorganosilylene group, a silalkylene structure, a silarylene structure, or a nitrogen-containing heterocyclic group; and divalent groups in which an alkylene group having 1 to 10 carbon atoms is bonded to a bond of a linear organopolysiloxane residue having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms.

[0044] Here, the group bonded to a silicon atom in a diorganosilylene group, a silalkylene structure, a silarylene structure, or an organopolysiloxane residue is preferably an alkyl group having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, such as a methyl group, an ethyl group, a propyl group, or a butyl group, or a phenyl group. Furthermore, the alkylene group in the silalkylene structure is preferably an ethylene group, a propylene group (trimethylene group, methylethylene group), a butylene group (tetramethylene group, methylpropylene group), or the like, having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. Furthermore, the organopolysiloxane residue may contain a silalkylene structure in which two silicon atoms are bonded via an alkylene group, such as an ethylene group or a propylene group.

[0045] Examples of such Y include the following groups. In the following structure, the left bond is bonded to Z, and the right bond is bonded to A. -O-(CH ２ ) ａ - (In the formula, a is an integer of 1 to 10, b, c, and d are each an integer of 1 to 8, the sum of b and c is an integer of 2 to 10, and the sum of b, c, and d is an integer of 3 to 10. e is an integer of 1 to 9, and f is an integer of 2 to 4.)

[0046] In the above formula (1), A independently represents the following general formula (2): (In the formula, R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, n" is a number from 0 to 3, n'" is an integer from 0 to 2, the sum of n" and n'" is a number of 3 or less, and n' is (3-(n"+n'")) / 2.)

[0047] In the above formula (2), n" is a number from 0 to 3 (0 or a positive number of 3 or less), preferably n"<3, and more preferably n"=0. n'" is an integer from 0 to 2, and preferably n'"=0. The sum of n" and n'" is a number of 3 or less. When n"+n'"=3 in the above formula (2), the above general formula (1) represents the molecular formula (structural formula) of a hydrocarbon terminal group-containing compound (monomer), and when n"+n'"<3 in the above formula (2), the above general formula (1) represents the composition formula of a polymer of a hydrocarbon terminal group-containing compound (polysilazane compound). In the above formula (2), n' is (3-(n"+n'")) / 2, and preferably 1.5.

[0048] In the above formula (1), k1 is an integer of 1 to 3, preferably 2 or 3, k2 is 0 or 1, k3 is 1 or 2, k1 + k2 + k3 is 2, 3 or 4 (i.e., when U is a single bond, k1 is 1, k2 is 0, and k3 is 1, and when U is other than a single bond, k1 + k2 + k3 is 3 or 4), when U is trivalent, k1 + k2 + k3 is 3, and when U is tetravalent, k1 + k2 + k3 is 4. Also, m is an integer of 1 to 7, preferably an integer of 1 to 3.

[0049] Examples of the structure of the hydrocarbon terminal group-containing compound represented by the above formula (1) include the following structures: 1 , R 2 By changing the combination of U, V, Z, Y, A, k1, k2, k3, and m, several hydrocarbon end group-containing compounds can be obtained.

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] (In the formula, x, y, y', z, q, r, s, a, b, c, d, e, and f are each independently the same as above.)

[0064] Examples of methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following methods: [Preparation Method 1] A hydrocarbon terminal group-containing compound having an alkenyl group at its terminal and a compound having a SiH group and a halosilyl group are mixed, and a hydrosilylation addition reaction is carried out in the presence of a hydrosilylation reaction catalyst. The resulting compound is then reacted with ammonia gas to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly, a compound having an amino group-containing silyl group at its terminal and / or a polysilazane compound, which is a polymer thereof).

[0065] Here, examples of hydrocarbon terminal group-containing compounds having an alkenyl group at the terminal include compounds represented by the following formula (1A). (In the formula, R 1 , R 2 , U, V, Z, k1, k2, k3, k1+k2+k3, m are the same as above. 1 are independently a single bond or a divalent hydrocarbon group having 1 to 18 carbon atoms, which may contain at least one atom selected from oxygen, nitrogen, sulfur and silicon atoms.

[0066] In the above formula (1A), Y 1 are each independently a single bond or a divalent hydrocarbon group having 1 to 18 carbon atoms, which may contain at least one atom selected from oxygen, nitrogen, sulfur, and silicon atoms, and examples thereof include those shown below. In the following structure, the bond on the left is bonded to Z, and the bond on the right is bonded to a carbon atom. (In the formula, a' is independently an integer of 0 to 8, b and c are each an integer of 1 to 8, c' and d' are each an integer of 0 to 6, the sum of b and c' is an integer of 2 to 8, and the sum of b, c, and d' is an integer of 3 to 8. e is an integer of 1 to 9, and f is an integer of 2 to 4.)

[0067] Examples of the compound represented by formula (1A) include the compounds shown below. (In the formula, x, y, y', z, q, a, a', b, c, and c' are each independently the same as above.)

[0068] In Preparation Method 1, examples of the compound having a SiH group and a halosilyl group include trichlorosilane, methyldichlorosilane, dimethylchlorosilane, and tribromosilane.

[0069] In Preparation Method 1, the amount of the compound having an SiH group and a halosilyl group used is preferably 1 to 6 moles, particularly 1.5 to 4 moles, per mole of alkenyl group in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0070] In Preparation Method 1, examples of the hydrosilylation catalyst include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinylsiloxanes, acetylene alcohols, and the like, and platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and chlorotris(triphenylphosphine)rhodium. Platinum compounds such as vinylsiloxane coordination compounds are preferred. Platinum compounds are preferably used by dissolving them in a solvent such as toluene, a lower alcohol, a higher alcohol, or a silicone-based solvent. The amount of the hydrosilylation catalyst used is preferably 0.001 to 1,000 ppm, preferably 0.01 to 100 ppm, in terms of transition metal (mass), relative to the mass of the compound containing a hydrocarbon terminal group having an alkenyl group at its terminal.

[0071] A solvent can be used during the reaction in Preparation Method 1. Examples of the solvent include aromatic hydrocarbons such as toluene and xylene, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane and cyclohexane, cyclic ether compounds such as tetrahydrofuran and dioxane, and ketones such as acetone and methyl ethyl ketone. The amount of the solvent used is 0 to 1,000 parts by mass, preferably 50 to 500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0072] In Preparation Method 1, the reaction conditions for the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with the compound having an SiH group and a halosilyl group are preferably a temperature of 20 to 120°C, particularly 40 to 100°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0073] In Preparation Method 1, the amount of ammonia gas used is preferably 1 to 300 cc / min, and particularly preferably 30 to 200 cc / min.

[0074] In Preparation Method 1, the reaction conditions for the reaction of the reaction product of a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with a compound having an SiH group and a halosilyl group with ammonia gas are preferably room temperature (23±15°C, the same applies hereinafter), particularly a temperature of 20 to 30°C, for 2 to 36 hours, particularly 4 to 12 hours.

[0075] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following: [Preparation Method 2] A hydrocarbon terminal group-containing compound having a terminal SiH group is mixed with a compound having an alkenyl group and a halosilyl group, and the mixture is subjected to a hydrosilylation addition reaction in the presence of a hydrosilylation reaction catalyst. The resulting compound is then reacted with ammonia gas to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly, a compound having an amino group-containing silyl group at its terminal and / or a polysilazane compound, which is a polymer thereof).

[0076] Examples of hydrocarbon terminal group-containing compounds having SiH groups at their terminals include compounds represented by the following formula (1B) or (1C): (In the formula, R 1 , R 2 , U, V, Z, k1, k2, k3, k1+k2+k3, m are the same as above. Z 1 is a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, and having a valence of 3 to 8, and m hydrogen atoms in formula (1B) are Z １ It bonds to the silicon atom in Y. 2 are independently a monovalent hydrocarbon group having a silicon atom or a siloxane bond and a terminal SiH group.

[0077] In the above formula (1B), Z 1 is a linear organopolysiloxane residue having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms, with a valence of 3 to 8, and examples thereof include those shown below. In the following structure, the bond on the left is bonded to V, and the other bonds are bonded to H. (wherein f is an integer of 2 to 4.)

[0078] Examples of the compound represented by formula (1B) include the compounds shown below. (In the formula, x, q, r, and s are each independently the same as above.)

[0079] In the above formula (1C), Y 2 are monovalent hydrocarbon groups each independently having a silicon atom or a siloxane bond and a terminal SiH group, examples of which include those shown below. (In the formula, b is an integer of 1 to 8, e is an integer of 1 to 9, and f is an integer of 2 to 4.)

[0080] Examples of the compound represented by formula (1C) include the compounds shown below. (In the formula, x and b are each independently the same as above.)

[0081] In Preparation Method 2, examples of the compound having an alkenyl group and a halosilyl group include vinyltrichlorosilane, allyltrichlorosilane, and octenyltrichlorosilane.

[0082] In Preparation Method 2, the amount of the compound having an alkenyl group and a halosilyl group used is preferably 1 to 5 moles, particularly 1 to 3 moles, per mole of SiH group in the hydrocarbon terminal group-containing compound having an SiH group at the terminal.

[0083] In Preparation Method 2, examples of the hydrosilylation catalyst include the same as those in Preparation Method 1. Platinum compounds such as vinylsiloxane coordination compounds are preferred. The platinum compounds are preferably used by dissolving them in a solvent such as toluene, a lower alcohol, a higher alcohol, or a silicone-based solvent. The amount of the hydrosilylation catalyst used is preferably 0.001 to 1,000 ppm, and more preferably 0.01 to 100 ppm, in terms of transition metal (by mass), relative to the mass of the hydrocarbon terminal group-containing compound having a terminal SiH group.

[0084] In Preparation Method 2, a solvent can be used during the reaction. Examples of the solvent include the same solvents as those used in Preparation Method 1. The amount of the solvent used is preferably 0 to 1,000 parts by mass, and more preferably 50 to 500 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a terminal SiH group.

[0085] In Preparation Method 2, the reaction conditions for the hydrocarbon terminal group-containing compound having a terminal SiH group with the compound having an alkenyl group and a halosilyl group are preferably a temperature of 20 to 120°C, particularly 40 to 100°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0086] In Preparation Method 2, the amount of ammonia gas used is preferably 1 to 300 cc / min, and particularly preferably 30 to 200 cc / min.

[0087] In Preparation Method 2, the reaction conditions for the reaction of the reaction product of a hydrocarbon terminal group-containing compound having a terminal SiH group with a compound having an alkenyl group and a halosilyl group with ammonia gas are preferably room temperature (23±15°C, the same applies hereinafter), particularly 20 to 30°C, for 2 to 36 hours, particularly 4 to 12 hours.

[0088] The present invention further provides a substantially fluorine-free surface treatment agent containing, as a main component, the above-mentioned hydrocarbon terminal group-containing compound, particularly the non-fluorine-containing hydrocarbon terminal group-containing compound represented by formula (1) above (i.e., having no fluorine atoms in the molecule). The surface treatment agent need only contain, as a main component, the above-mentioned hydrocarbon terminal group-containing compound, particularly the hydrocarbon terminal group-containing compound represented by formula (1), and may also contain unreacted raw materials or reaction intermediates prior to the introduction of reactive groups into the hydrocarbon terminal group-containing compound represented by formula (1). Furthermore, the surface treatment agent may also contain a partial hydrolysis condensate obtained by partially hydrolyzing the reactive silazane groups of the hydrocarbon terminal group-containing compound in advance by a known method.

[0089] If necessary, the surface treatment agent may contain a hydrolysis and condensation catalyst, such as an organotin compound (dibutyltin dimethoxide, dibutyltin dilaurate, etc.), an organotitanium compound (tetra n-butyl titanate, tetra n-propyl titanate, etc.), an organozirconium compound (tetra n-butyl zirconate, tetra n-propyl zirconate, etc.), an organic acid (acetic acid, methanesulfonic acid, carboxylic acid, etc.), an inorganic acid (hydrochloric acid, sulfuric acid, etc.), or an organic base (amine, trialkylamine, nitrogen-containing cyclic compound, etc.). Of these, acetic acid, tetra n-butyl titanate, dibutyltin dilaurate, etc. are particularly desirable. The amount of the hydrolysis and condensation catalyst added is a catalytic amount, and is typically 0.001 to 5 parts by mass, particularly 0.1 to 1 part by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound (and / or its partial hydrolysis and condensate).

[0090] The surface treatment agent may contain a suitable solvent. Such a solvent is preferably a non-fluorinated solvent, and examples thereof include hydrocarbon solvents (petroleum benzine, toluene, xylene, hexane, cyclohexane, methylcyclohexane, ethylcyclohexane, heptane, octane (n-octane, isooctane, etc.), nonane (n-nonane, isononane, etc.)), ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, etc.), ether solvents (tetrahydrofuran (THF), dipropyl ether, dibutyl ether, methylcyclopentyl ether, methyl t-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, propylene glycol dimethyl ether, etc.), alcohol solvents (propylene glycol monomethyl ether, butanol, isopropanol, etc.), and ester solvents (ethyl acetate, propyl acetate, butyl acetate, pentyl acetate, propylene glycol monomethyl ether acetate). Among these, toluene, hexane, heptane, isooctane, isononane, cyclopentanone, dipropyl ether, dibutyl ether, methyl cyclopentyl ether, methyl t-butyl ether, ethylene glycol dimethyl ether, propyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate are preferred in terms of solubility, wettability, and the like.

[0091] Two or more of the above solvents may be mixed, and it is preferable to uniformly dissolve the hydrocarbon terminal group-containing compound (and its partial hydrolysis condensate). The optimal concentration of the hydrocarbon terminal group-containing compound (and its partial hydrolysis condensate) to be dissolved in the solvent varies depending on the treatment method, and may be any amount that is easy to weigh. In the case of direct coating, the amount is preferably 0.01 to 100 parts by mass, and more preferably 0.05 to 30 parts by mass, per 100 parts by mass of the solvent and the hydrocarbon terminal group-containing compound (and its partial hydrolysis condensate). In the case of vapor deposition treatment, the amount is preferably 1 to 100 parts by mass, and more preferably 3 to 30 parts by mass, per 100 parts by mass of the solvent and the hydrocarbon terminal group-containing compound (and its partial hydrolysis condensate). In either case, the amount of 100 parts by mass refers to coating directly without using a solvent.

[0092] The surface treatment agent of the present invention can be applied to a substrate by known methods such as brushing, dipping, spraying, and vapor deposition. The heating method during vapor deposition may be either resistance heating or electron beam heating, and is not particularly limited. The curing conditions vary depending on the curing method. For example, in the case of direct coating (brushing, dipping, spraying, etc.), the curing conditions are preferably 25 to 200°C, particularly 25 to 150°C, for 30 minutes to 36 hours, particularly 1 to 24 hours. In the case of application by vapor deposition, the curing conditions are preferably 20 to 200°C, for 1 to 24 hours. Furthermore, the curing may be carried out under humid conditions.

[0093] The thickness of the cured coating is determined appropriately depending on the type of substrate, but is usually 0.1 to 100 nm, particularly 1 to 20 nm. The thickness can be measured by, for example, spectral reflectance measurement, X-ray reflectance measurement, spectroscopic ellipsometry measurement, X-ray fluorescence measurement, etc.

[0094] The substrate to be treated with the surface treatment agent of the present invention is not particularly limited and may be made of various materials such as paper, cloth, metal and its oxides, glass, plastic, ceramic, and quartz. The surface treatment agent of the present invention can impart water and oil repellency to the above substrates. In particular, it can be suitably used as a surface treatment agent for SiO-treated glass or film.

[0095] The surface treatment agent of the present invention can form a cured coating film that has high levels of water repellency, slipperiness, dirt wiping properties and abrasion resistance.

[0096] Examples of articles that can be treated with the surface treatment agent of the present invention include optical articles and electronic components such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game machines, eyeglass lenses, camera lenses, lens filters, sunglasses, medical devices such as gastroscopes, copiers, PCs, liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, and anti-reflection films. The surface treatment agent of the present invention can impart scratch resistance to the above-mentioned articles, and is therefore particularly useful as a water-repellent layer for touch panel displays, anti-reflection films, eyeglass lenses, etc.

[0097] The surface treatment agent of the present invention is also useful as an anti-fouling coating for sanitary products such as bathtubs and washbasins, an anti-fouling coating for window glass or tempered glass for automobiles, trains, aircraft, etc., and headlamp covers, a water-repellent coating for exterior wall building materials, a stain-resistant coating for kitchen building materials, an anti-fouling coating for telephone booths and to prevent posters and graffiti, a coating that provides stain resistance for artworks, etc., and a stain-resistant coating for compact discs, DVDs, etc. The hydrocarbon terminal group-containing compound of the present invention can also be suitably used as a release agent or paint additive for molds, a resin modifier, a flowability modifier or dispersibility modifier for inorganic fillers, or a lubricity improver for tapes, films, etc.

[0098] The present invention will be described in more detail below with reference to synthesis examples, examples, and comparative examples. However, the present invention is not limited to the following examples. In the following examples, the molar amount of a compound is expressed as the molar amount of the compound relative to the measured mass of the target compound. 1 The film thickness was measured by spectroscopic ellipsometry using a spectroscopic ellipsometer. The room temperature was 23°C.

[0099] Synthesis Example 1 A reaction vessel was charged with a compound represented by the following formula (A): 1.00 g (1.37 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.556 g (4.11 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 5.23 × 10 -3 g (1.62 x 10 as Pt alone) -8 The resulting mixture (containing 1.5 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 0.950 g of product.

[0100] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (B):

[0101] Synthesis Example 2 A reaction vessel was charged with a compound represented by the following formula (C): 1.00 g (1.97 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.802 g (5.92 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.54 × 10 -3 g (2.33 x 10 as Pt alone) -8 The resulting mixture (containing 1.0 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.01 g of product.

[0102] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (D):

[0103] Synthesis Example 3 A reaction vessel was charged with a compound represented by the following formula (E): 1.00 g (1.29 × 10-3 mol), toluene 1.00 g, trichlorosilane 0.526 g (3.88 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 4.94 × 10 -3 g (1.53 x 10 as Pt alone) -8 The resulting mixture (containing 1.25 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.10 g of product.

[0104] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (F):

[0105] Synthesis Example 4 A reaction vessel was charged with a compound represented by the following formula (G): 1.00 g (1.82 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.740 g (5.47 × 10 -3 mol), and 6.96 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -3 g (2.15 x 10 as Pt alone) -8 The resulting mixture (containing 1.5 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 0.99 g of product.

[0106] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (H):

[0107] Synthesis Example 5 A reaction vessel was charged with a compound represented by the following formula (I): 1.00 g (1.59 × 10 -3mol), toluene 1.00 g, trichlorosilane 0.644 g (4.76 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 6.06 × 10 -3 g (1.87 x 10 as Pt alone) -8 The resulting mixture (containing 1.5 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 0.94 g of product.

[0108] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (J):

[0109] Synthesis Example 6 A reaction vessel was charged with a compound represented by the following formula (K): 1.00 g (1.51 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.615 g (4.54 × 10 -3 mol), and 5.78 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -3 g (1.79 x 10 as Pt alone) -8 The resulting mixture (containing 1.5 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 0.98 g of product.

[0110] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (L):

[0111] Synthesis Example 7 A reaction vessel was charged with a compound represented by the following formula (M): 1.00 g (1.38 × 10 -3 mol), toluene 1.00 g, allyltrichlorosilane 0.718 g (4.13 × 10-3 mol), and 5.26 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -3 g (1.62 x 10 as Pt alone) -8 The resulting mixture (containing 1.25 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.14 g of product.

[0112] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (N):

[0113] Synthesis Example 8 A reaction vessel was charged with a compound represented by the following formula (O): 1.00 g (1.29 × 10 -3 mol), toluene 2.00 g, vinyltrichlorosilane 1.85 g (1.16 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 4.92 × 10 -3 g (1.52 x 10 as Pt alone) -8 The resulting mixture (containing 1.56 mol) was mixed with 3.00 g of toluene and aged for 24 hours at 60°C. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.56 g of product.

[0114] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (P):

[0115] Synthesis Example 9 A reaction vessel was charged with a compound represented by the following formula (Q): 1.00 g (1.55 × 10 -3 mol), toluene 1.00 g, methyldichlorosilane 1.07 g (9.32 × 10 -3mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 5.93 × 10 -3 g (1.83 x 10 as Pt alone) -8 The resulting mixture (containing 1.0 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.07 g of product.

[0116] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (R):

[0117] Synthesis Example 10 A reaction vessel was charged with a compound represented by the following formula (S): 1.00 g (9.60 × 10 -4 mol), toluene 1.00 g, trichlorosilane 0.392 g (2.89 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 3.68 × 10 -3 g (1.14 x 10 as Pt alone) -8 The resulting mixture (containing 1.5 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 0.99 g of product.

[0118] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (T):

[0119] Synthesis Example 11 A reaction vessel was charged with a compound represented by the following formula (U): 1.00 g (1.48 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.603 g (4.45 × 10 -3 mol), and 5.67 × 10 chloroplatinic acid / vinylsiloxane complex in toluene-3 g (1.75 x 10 as Pt alone) -8 The resulting mixture (containing 1.25 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.10 g of product.

[0120] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (V):

[0121] Synthesis Example 12 A reaction vessel was charged with a compound represented by the following formula (W): 1.00 g (1.69 × 10 -3 mol), toluene 1.00 g, dimethylchlorosilane 0.481 g (5.08 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 6.47 × 10 -3 g (2.00 x 10 as Pt alone) -8 The resulting mixture (containing 1.25 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.11 g of product.

[0122] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (X):

[0123] Synthesis Example 13 A reaction vessel was charged with a compound represented by the following formula (Y): 1.00 g (1.25 × 10 -3 mol), toluene 1.00 g, trichlorosilane 1.01 g (7.49 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 4.77 × 10 -3 g (1.47 x 10 as Pt alone) -8The resulting mixture (containing 1.0 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.06 g of product.

[0124] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (Z):

[0125] Synthesis Example 14 A reaction vessel was charged with a compound represented by the following formula (AA): 1.00 g (2.38 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.966 g (7.14 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 9.08 × 10 -3 g (2.81 x 10 as Pt alone) -8 The resulting mixture (containing 1.25 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.25 g of product.

[0126] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AB):

[0127] Synthesis Example 15 A reaction vessel was charged with a compound represented by the following formula (AC): 1.00 g (3.22 × 10 -3 mol), toluene 1.00 g, trichlorosilane 1.31 g (9.67 × 10 -3 mol), and 1.23 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (3.80 x 10 as Pt alone) -8The resulting mixture (containing 1.29 mol) was mixed with 3.00 g of toluene and aged for 24 hours at 60°C. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.29 g of product.

[0128] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AD):

[0129] Synthesis Example 16 A reaction vessel was charged with a compound represented by the following formula (AE): 1.00 g (2.84 × 10 -3 mol), toluene 1.00 g, trichlorosilane 1.15 g (8.51 × 10 -3 mol), and 1.08 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (3.35 x 10 as Pt alone) -8 The resulting mixture (containing 1.25 mol) was mixed with 3.00 g of toluene and aged at 60°C for 24 hours. The solvent and unreacted materials were then distilled off under reduced pressure. The resulting product was mixed with 3.00 g of toluene and aged for 6 hours at room temperature while bubbling ammonia gas (ammonia gas used at a rate of 40 cc / min). The mixture was then filtered, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.30 g of product.

[0130] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AF):

[0131] Example 1 The compound obtained in Synthesis Example 1 was dissolved in toluene to a concentration of 10% by mass to prepare a surface treatment agent.

[0132] Example 2 The compound obtained in Synthesis Example 2 was dissolved in dibutyl ether to a concentration of 20% by mass to prepare a surface treatment agent.

[0133] Example 3 The compound obtained in Synthesis Example 3 was dissolved in butyl acetate to a concentration of 10% by mass to prepare a surface treatment agent.

[0134] Example 4 The compound obtained in Synthesis Example 4 was dissolved in dibutyl ether to a concentration of 30% by mass to prepare a surface treatment agent.

[0135] Example 5 The compound obtained in Synthesis Example 7 was dissolved in toluene to a concentration of 50% by mass to prepare a surface treatment agent.

[0136] Example 6 The compound obtained in Synthesis Example 9 was dissolved in butyl acetate to a concentration of 70% by mass to prepare a surface treatment agent.

[0137] Example 7 The compound obtained in Synthesis Example 11 was dissolved in dibutyl ether to a concentration of 5% by mass to prepare a surface treatment agent.

[0138] Example 8 The compound obtained in Synthesis Example 13 was dissolved in propylene glycol monomethyl ether acetate to a concentration of 30% by mass to prepare a surface treatment agent.

[0139] Example 9 The compound obtained in Synthesis Example 14 was dissolved in toluene to a concentration of 80% by mass to prepare a surface treatment agent.

[0140] Example 10 The compound obtained in Synthesis Example 15 was dissolved in a mixed liquid of isononane / isooctane (mass ratio 50 / 50) to a concentration of 90 mass % to prepare a surface treatment agent.

[0141] Example 11 The compound obtained in Synthesis Example 4 was used as a surface treatment agent without dilution.

[0142] Example 12 The compound obtained in Synthesis Example 16 was used as a surface treatment agent without dilution.

[0143] [Comparative Example 1] The following formula (A') A surface treatment agent was prepared by dissolving a compound represented by the following formula in toluene to a concentration of 20 mass %.

[0144] [Comparative Example 2] The following formula (B') A surface treatment agent was prepared by dissolving a compound represented by the following formula in toluene to a concentration of 20 mass %.

[0145] [Comparative Example 3] The following formula (C') A surface treatment agent was prepared by dissolving a compound represented by the following formula in toluene to a concentration of 20 mass %.

[0146] Comparative Example 4 No surface treatment agent.

[0147] Formation of a cured film for evaluating rapid curing properties Each of the surface treatment agents prepared in the above Examples and Comparative Examples was vacuum-deposited (apparatus: ULVAC Kiko Co., Ltd., product number: VTR-350M) onto glass (Corning Gorilla Glass (product number: Gorilla III, size: 100 mm × 50 mm × 0.7 mm)) whose outermost surface had been coated with SiO2 to a thickness of 10 nm under the following conditions (treatment conditions: pressure: 2.0 × 10 -2 The coating was cured for 30 minutes under an atmosphere of 25°C and 50% relative humidity (heating temperature: 700°C), 25°C, and a thickness of 3 to 5 nm to form a cured coating for evaluating rapid curing properties. [SiO2 layer deposition conditions] Coating device: OTFC-1300 (manufactured by Optran Co., Ltd.) Coating material: SiO2 Coating chamber pressure: 0.015 Pa Coating rate: 0.8 nm / s Coating thickness: 10 nm

[0148] The glass on which the cured coating was formed was evaluated for rapid curing properties by the following method. Note that a glass (Gorilla Glass (product number: Gorilla III, size: 100 mm x 50 mm x 0.7 mm) manufactured by Corning Incorporated) that had not been surface-treated and had been coated with SiO to a thickness of 10 nm on its outermost surface was used as is as Comparative Example 4 and was evaluated in the same manner.

[0149] Evaluation of Rapid Curing Property For the glass on which the cured coating prepared above was formed, the contact angle (water repellency) of the cured coating with water was measured using a contact angle meter Drop Master (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25° C., relative humidity: 40%). The measurement was performed by photographing the droplet 1 second after it was dropped with a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software attached to the contact angle meter, to measure the contact angle between the glass substrate and the droplet. The contact angle was calculated using the θ / 2 method. The analysis conditions were as follows. The results are shown in Table 1. In the present invention, a good (water-repellent) water contact angle was defined as 90° or more, and a result of 90° or more was considered to have good rapid curing property (the same applies hereinafter). [Analysis conditions] Method: Droplet method (θ / 2 method) Droplet recognition: Automatic Droplet recognition line (distance from needle tip): 50 dots Algorithm: Automatic Image mode: Frame threshold level: Automatic

[0150] Formation of various cured coatings for evaluation Each of the surface treatment agents prepared in the above Examples and Comparative Examples was vacuum-deposited (apparatus: ULVAC Kiko Co., Ltd., product number: VTR-350M) onto glass (Corning Gorilla Glass (product number: Gorilla III, size: 100 mm x 50 mm x 0.7 mm)) whose outermost surface had been coated with SiO2 to a thickness of 10 nm under the following conditions (treatment conditions: pressure: 2.0 x 10 -2 The coating was then cured for 1 hour at 80°C and 80% relative humidity, and then for 12 hours at 25°C and 50% relative humidity to form various cured coatings for evaluation with thicknesses of 3 to 5 nm. [SiO2 layer deposition conditions] Coating apparatus: OTFC-1300 (manufactured by Optran Co., Ltd.) Coating material: SiO2 Coating chamber pressure: 0.015 Pa Coating rate: 0.8 nm / s Coating thickness: 10 nm

[0151] The glass having the above-described cured coating formed thereon was evaluated for water repellency, slipperiness, dirt wiping ability, and abrasion resistance by the following methods. Note that the same evaluation was carried out for Comparative Example 4 using glass (Gorilla Glass (product number: Gorilla III, size: 100 mm × 50 mm × 0.7 mm) manufactured by Corning Incorporated) coated on its outermost surface with SiO2 to a thickness of 10 nm without surface treatment.

[0152] Evaluation of Water Repellency For the glass having the cured coating formed thereon, the contact angle (water repellency) of the cured coating with water was measured using a contact angle meter Drop Master (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25° C., relative humidity: 40%). The measurement was performed by photographing the droplet 1 second after it was dropped with a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software attached to the contact angle meter, to measure the contact angle between the glass substrate and the droplet. The contact angle was calculated using the θ / 2 method. The analysis conditions were as follows. The results are shown in Table 1. In the present invention, a water contact angle of 90° or more was defined as a good (water-repellent) water contact angle (the same applies hereinafter). [Analysis conditions] Method: Droplet method (θ / 2 method) Droplet recognition: Automatic Droplet recognition line (distance from needle tip): 50 dots Algorithm: Automatic Image mode: Frame threshold level: Automatic

[0153] Evaluation of Slipperiness The coefficient of dynamic friction of the glass having the cured coating formed thereon as prepared above against nonwoven fabric was evaluated by the method described below to evaluate the slipperiness. The coefficient of dynamic friction of the glass having the cured coating formed against nonwoven fabric was measured in accordance with ASTM D1894 using a surface property measuring instrument Type: 14FW (manufactured by Shinto Scientific Co., Ltd.) under conditions of a load of 100 gf and a tensile speed of 500 mm / min. The results (coefficient of dynamic friction) are shown in Table 1. [Conditions for evaluating slipperiness] Load: 100 gf Stroke: 100 mm Contact area: 1 x 3 cm 2 Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation)

[0154] Evaluation of Dirt Wiping Ability A 2 cm straight line was drawn on the glass surface on which the cured coating prepared above was formed using a Hi-Mackey (manufactured by Zebra), the ink was allowed to dry, and the ink was then wiped off with tissue paper. The number of times the ink was rubbed until it was wiped off was evaluated according to the following criteria. The results are shown in Table 1. [Dirt Wiping Ability Evaluation Criteria] A: 4 or fewer rubs B: 5 or more rubs C: Ink could not be wiped off

[0155] Evaluation of Abrasion Resistance: The glass on which the cured coating prepared above was formed was rubbed every 500 times using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions, and the contact angle (water repellency) of the cured coating with water was measured in the same manner as above. The number of times the contact angle became less than 80° was counted and used to evaluate abrasion resistance. The test environmental conditions were 25°C and a relative humidity of 40%. The results (the number of times the water contact angle became less than 80°) are shown in Table 1. [Steel wool abrasion resistance test conditions] Steel wool: Bonster #0000 Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2

[0156] The cured coatings of the surface treatment agents of Examples 1 to 12 exhibited improved hydrolysis rates due to the presence of silazane groups at the molecular chain terminals of the compounds used, resulting in faster adhesion to the substrate and faster development of water contact angles. Furthermore, the presence of hydrocarbon chains with a specific carbon number resulted in water repellency and improved molecular mobility, resulting in good slip properties, ease of wiping, and abrasion resistance. The cured coatings of the surface treatment agents of Comparative Examples 1 and 3 exhibited slow hydrolysis due to the alkoxysilyl groups at the molecular chain terminals of the compounds used, resulting in slow development of water contact angles. The cured coating of the surface treatment agent of Comparative Example 2 contained a fluorine-containing compound, and the compound used had a fluorohydrocarbon chain, resulting in fast development of a water contact angle (fast curing), but poor durability. Comparative Example 4 was a glass substrate without a surface treatment agent, but since it was not surface-treated, it lacked any of the characteristics, and the effects of the Examples could be confirmed. As described above, the surface treatment agents of the Examples were able to provide, in vapor deposition coating, cured coatings of non-fluorine-based hydrocarbon terminal group-containing compounds that exhibited fast curing properties and were excellent in high levels of water repellency, slipperiness, dirt wiping ability, and abrasion resistance.

[0157]

[0158] Example 13 The compound obtained in Synthesis Example 1 was dissolved in dibutyl ether to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0159] Example 14 The compound obtained in Synthesis Example 2 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0160] Example 15 The compound obtained in Synthesis Example 4 was dissolved in dibutyl ether to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0161] Example 16 The compound obtained in Synthesis Example 5 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0162] Example 17 The compound obtained in Synthesis Example 8 was dissolved in a hexane / isooctane mixture (mass ratio 50 / 50) to a concentration of 0.1 mass % to prepare a surface treatment agent.

[0163] Example 18 The compound obtained in Synthesis Example 12 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0164] Example 19 The compound obtained in Synthesis Example 14 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0165] Comparative Example 5 The compound represented by the above formula (A') was dissolved in dibutyl ether to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0166] Comparative Example 6 The compound represented by the above formula (B') was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0167] Comparative Example 7 The compound represented by the above formula (C') was dissolved in dibutyl ether to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0168] [Comparative Example 8] No surface treatment agent.

[0169] Formation of a cured coating for evaluating rapid curing properties Each of the surface treatment agents prepared in the above Examples and Comparative Examples was spray coated onto glass (Corning Gorilla Glass (product number: Gorilla III, size: 100 mm x 50 mm x 0.7 mm)) under the following conditions, and cured for 30 minutes under an atmosphere of 80°C and 80% relative humidity and an atmosphere of 25°C and 50% relative humidity to form a cured coating with a film thickness of 3 to 5 nm for evaluating rapid curing properties. [Spray coating conditions] Atmosphere: 25°C / 50% Nozzle distance: 50 mm Air pressure: 150 kPa Speed: 300 mm / min Pitch: 5 mm

[0170] The glass on which the cured coating was formed was evaluated for rapid curing properties by the following method. Note that the same evaluation was carried out for Comparative Example 8, except that no surface treatment was performed on glass (Gorilla Glass (product number: Gorilla III, size: 100 mm × 50 mm × 0.7 mm) manufactured by Corning Incorporated).

[0171] Evaluation of Rapid Curing Properties For the glass on which the cured coating prepared above was formed, the contact angle (water repellency) of the cured coating with respect to water was measured using a contact angle meter Drop Master (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25° C., relative humidity: 40%). The measurement was performed by photographing the droplet 1 second after it was dropped with a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software attached to the contact angle meter, to measure the contact angle between the glass substrate and the droplet. The contact angle was calculated using the θ / 2 method. The analysis conditions were as follows. The results are shown in Table 2. [Analysis Conditions] Method: Droplet method (θ / 2 method) Droplet recognition: Automatic Droplet recognition line (distance from needle tip): 50 dots Algorithm: Automatic Image mode: Frame threshold level: Automatic

[0172] Formation of various cured coatings for evaluation Each of the surface treatment agents prepared in the above Examples and Comparative Examples was spray coated onto glass (Corning Gorilla Glass (product number: Gorilla III, size: 100 mm x 50 mm x 0.7 mm)) under the following conditions, and cured for 1 hour in an atmosphere of 80°C and 80% relative humidity, and then for 12 hours in an atmosphere of 25°C and 50% relative humidity to form various cured coatings for evaluation with a film thickness of 3 to 5 nm. [Spray coating conditions] Atmosphere: 25°C / 50%, Nozzle distance: 50 mm, Air pressure: 150 kPa, Speed: 300 mm / min, Pitch: 5 mm

[0173] The glass on which the cured coating was formed was evaluated for water repellency, slipperiness, dirt wiping ability, and abrasion resistance by the following methods. The same evaluations were carried out for Comparative Example 8, except that no surface treatment was performed on glass (Gorilla Glass (product number: Gorilla III, size: 100 mm × 50 mm × 0.7 mm) manufactured by Corning Incorporated).

[0174] Evaluation of Water Repellency For the glass on which the cured coating prepared above was formed, the contact angle (water repellency) of the cured coating with respect to water was measured using a contact angle meter Drop Master (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25° C., relative humidity: 40%). The measurement was performed by photographing the droplet 1 second after it was dropped with a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software attached to the contact angle meter, to measure the contact angle between the glass substrate and the droplet. The contact angle was calculated using the θ / 2 method. The analysis conditions were as follows. The results are shown in Table 2. [Analysis Conditions] Method: Droplet method (θ / 2 method) Droplet recognition: Automatic Droplet recognition line (distance from needle tip): 50 dots Algorithm: Automatic Image mode: Frame threshold level: Automatic

[0175] Evaluation of Slipperiness The glass having the cured coating formed thereon prepared as described above was evaluated for its slipperiness by measuring the coefficient of dynamic friction against nonwoven fabric using the method described below. The coefficient of dynamic friction of the glass having the cured coating formed thereon against nonwoven fabric was measured in accordance with ASTM D1894 using a surface property measuring instrument Type: 14FW (manufactured by Shinto Scientific Co., Ltd.) under conditions of a load of 100 gf and a tensile speed of 500 mm / min. The results (coefficient of dynamic friction) are shown in Table 2. [Conditions for evaluating slipperiness] Load: 100 gf Stroke: 100 mm Contact area: 1 x 3 cm 2 Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation)

[0176] Evaluation of Dirt Wiping Ability A 2 cm straight line was drawn on the glass surface on which the cured coating prepared above was formed using a Hi-Mackey (manufactured by Zebra), the ink was allowed to dry, and the ink was then wiped off with tissue paper. The number of times the ink was rubbed until it was wiped off was evaluated according to the following criteria. The results are shown in Table 2. [Dirt Wiping Ability Evaluation Criteria] A: 4 or fewer rubs B: 5 or more rubs C: Ink could not be wiped off

[0177] Evaluation of Abrasion Resistance: The glass on which the cured coating prepared above was formed was rubbed every 500 times using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions, and the contact angle (water repellency) of the cured coating with water was measured in the same manner as above. The number of times the contact angle became less than 80° was counted and used to evaluate abrasion resistance. The test environmental conditions were 25°C and a relative humidity of 40%. The results (the number of times the water contact angle became less than 80°) are shown in Table 2. [Steel wool abrasion resistance test conditions] Steel wool: Bonster #0000 Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2

[0178] The cured coatings of the surface treatment agents of Examples 13 to 19 exhibited improved hydrolysis rates due to the presence of silazane groups at the molecular chain terminals of the compounds used, resulting in faster adhesion to the substrate and faster development of a water contact angle. Furthermore, the presence of hydrocarbon chains with a specific carbon number resulted in water repellency and improved molecular mobility, resulting in good slip properties, ease of wiping, and abrasion resistance. The cured coatings of the surface treatment agents of Comparative Examples 5 and 7 exhibited slow hydrolysis due to the alkoxysilyl groups at the molecular chain terminals of the compounds used, resulting in slow development of a water contact angle. The cured coating of the surface treatment agent of Comparative Example 6 contained a fluorine-containing compound, and the compound used had a fluorohydrocarbon chain, resulting in fast development of a water contact angle (fast curing), but poor durability. Comparative Example 8 was a glass substrate without a surface treatment agent, but since it was not surface-treated, it lacked any of the characteristics, and the effects of the Examples could be confirmed. As described above, the surface treatment agents of the Examples were able to provide, even when spray-coated, cured coatings of non-fluorine-based hydrocarbon terminal group-containing compounds that exhibited fast curing properties and were excellent in high levels of water repellency, slipperiness, dirt-wiping ability, and abrasion resistance.

[0179]

[0180] Example 20 The compound obtained in Synthesis Example 1 was dissolved in toluene to a concentration of 10% by mass to prepare a surface treatment agent.

[0181] Example 21 The compound obtained in Synthesis Example 1 was dissolved in toluene to a concentration of 10% by mass to prepare a surface treatment agent.

[0182] Comparative Example 9 A surface treatment agent was prepared by dissolving the compound represented by formula (C') in toluene to a concentration of 10 mass %.

[0183] Comparative Example 10 A surface treatment agent was prepared by dissolving the compound represented by formula (C') in toluene to a concentration of 10 mass %.

[0184] Formation of cured coating for evaluating rapid curing properties Each of the surface treatment agents prepared in the above Examples and Comparative Examples was vacuum-deposited (apparatus: ULVAC Kiko Co., Ltd., product number: VTR-350M) onto SUS304 (manufactured by Standard Test Piece Co., Ltd., test piece substrate of 1 mm thickness, 50 mm width, and 100 mm length) and clear hard-coated PET film (Kimoto Co., Ltd., hard-coated film KB stick 50S01S, test piece substrate of 50 μm thickness, 50 mm width, and 100 mm length) (treatment conditions: pressure: 2.0 × 10 -2 The coating was cured for 30 minutes in an atmosphere of 25°C and 50% relative humidity (Pa, heating temperature: 700°C) to form a cured coating having a film thickness of 3 to 5 nm for evaluation of rapid curing properties.

[0185] The substrates on which the cured coatings were formed were evaluated for rapid curing properties by the following method.

[0186] Evaluation of Rapid Curing Properties For the substrates on which the cured coatings prepared above were formed, the contact angle (water repellency) of the cured coatings with respect to water was measured using a contact angle meter Drop Master (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25° C., relative humidity: 40%). The measurement was performed by photographing the droplet 1 second after it was dropped with a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software attached to the contact angle meter, to measure the contact angle between the substrate and the droplet. The contact angle was calculated using the θ / 2 method. The analysis conditions were as follows. The results are shown in Table 3. [Analysis Conditions] Method: Droplet method (θ / 2 method) Droplet recognition: Automatic Droplet recognition line (distance from needle tip): 50 dots Algorithm: Automatic Image mode: Frame threshold level: Automatic

[0187] Formation of various cured coatings for evaluation Each of the surface treatment agents prepared in the above Examples and Comparative Examples was vacuum-deposited (apparatus: ULVAC Kiko Co., Ltd., product number: VTR-350M) onto SUS304 (manufactured by Standard Test Piece Co., Ltd., test piece substrate of 1 mm thickness, 50 mm width, and 100 mm length) and clear hard-coated PET film (Kimoto Co., Ltd., hard-coated film KB Stick 50S01S, test piece substrate of 50 μm thickness, 50 mm width, and 100 mm length) (treatment conditions: pressure: 2.0 × 10 -2The coating was cured for 1 hour in an atmosphere of 80°C and 80% relative humidity, and then for 12 hours in an atmosphere of 25°C and 50% relative humidity, to form various cured coatings for evaluation with thicknesses of 3 to 5 nm.

[0188] The substrates on which the cured coatings were formed were evaluated for water repellency, slipperiness, dirt wiping ability, and abrasion resistance by the methods described below.

[0189] Evaluation of Water Repellency For the substrates on which the cured coatings prepared above were formed, the contact angle (water repellency) of the cured coatings with respect to water was measured using a contact angle meter Drop Master (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25° C., relative humidity: 40%). The measurement was carried out by photographing the droplet 1 second after it was dropped using a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software attached to the contact angle meter, to measure the contact angle between the substrate and the droplet. The contact angle was calculated using the θ / 2 method. The analysis conditions were as follows. The results are shown in Table 3. [Analysis Conditions] Method: Droplet method (θ / 2 method) Droplet recognition: Automatic Droplet recognition line (distance from needle tip): 50 dots Algorithm: Automatic Image mode: Frame threshold level: Automatic

[0190] Evaluation of Slipperiness The substrates having the cured coatings prepared above were evaluated for their slipperiness by measuring the coefficient of dynamic friction against nonwoven fabric using the method described below. The coefficient of dynamic friction of the substrates having the cured coatings formed thereon against nonwoven fabric was measured in accordance with ASTM D1894 using a surface property measuring instrument Type: 14FW (manufactured by Shinto Scientific Co., Ltd.) under conditions of a load of 100 gf and a tensile speed of 500 mm / min. The results (coefficient of dynamic friction) are shown in Table 3. [Conditions for evaluating slipperiness] Load: 100 gf Stroke: 100 mm Contact area: 1 x 3 cm 2 Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation)

[0191] Evaluation of Dirt Wiping Ability A 2 cm straight line was drawn on the substrate with the cured coating prepared above using a Hi-Mackey (manufactured by Zebra), after which the ink was dried and wiped off with tissue paper. The number of times it took to wipe off the ink was evaluated according to the following criteria. The results are shown in Table 3. [Dirt Wiping Ability Evaluation Criteria] A: 4 or fewer rubs B: 5 or more rubs C: Ink could not be wiped off

[0192] Evaluation of abrasion resistance: The substrate having the cured coating formed thereon was rubbed every 100 times using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions, and the contact angle (water repellency) of the cured coating with water was measured in the same manner as above. The number of times the contact angle became less than 80° was counted and used to evaluate abrasion resistance. The test environment conditions were 25°C and a relative humidity of 40%. The results (number of times the water contact angle became less than 80°) are shown in Table 3. [Conditions for fabric abrasion test] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 4 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2

[0193] The cured coatings of the surface treatment agents of Examples 20 and 21 exhibited improved hydrolysis rates due to the presence of silazane groups at the molecular chain terminals of the compounds used, resulting in faster adhesion to the substrate and faster development of water contact angles. Furthermore, the silazane groups strongly adhered to the substrate, resulting in good abrasion resistance. The cured coatings of the surface treatment agents of Comparative Examples 9 and 10 exhibited slow hydrolysis due to the presence of alkoxysilyl groups at the molecular chain terminals of the compounds used, resulting in slow development of water contact angles. Furthermore, the alkoxysilyl groups exhibited insufficient adhesion to various substrates, resulting in poor abrasion resistance. As described above, the surface treatment agents of the Examples were vapor-deposited to obtain cured coatings of non-fluorine-containing hydrocarbon terminal group-containing compounds that exhibited rapid curing, even on substrates other than glass, and exhibited high levels of water repellency, slip resistance, dirt wipeability, and abrasion resistance.

[0194]

Claims

1. A non-fluorine-based hydrocarbon end group-containing compound having at least one linear, branched or cyclic monovalent hydrocarbon end group having 3 to 60 carbon atoms and further having at least one reactive silazane group.

2. The hydrocarbon terminal group-containing compound according to claim 1, wherein the hydrocarbon terminal group is a group selected from alkyl groups having 6 to 28 carbon atoms and aryl groups having 6 to 32 carbon atoms.

3. The hydrocarbon terminal group-containing compound according to claim 1, which has two or more of the hydrocarbon terminal groups and has a trivalent or higher linking group between the hydrocarbon terminal group and the reactive silazane group.

4. The hydrocarbon terminal group-containing compound is represented by the following general formula (1): (In the formula, R 1 are monovalent hydrocarbon groups having 3 to 32 carbon atoms, which may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which may be linear, branched, or cyclic, or a combination thereof; R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group; V independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom; Z independently represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group; Y independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom; and A independently represents a group represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, n" is a number from 0 to 3, n'" is an integer from 0 to 2, the sum of n" and n'" is a number of 3 or less, and n' is (3-(n"+n'")) / 2), k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is 1 or 2, k1+k2+k3 is 2, 3, or 4, and m is an integer from 1 to 7.

5. In the above formula (1), R 1 5. The hydrocarbon terminal group-containing compound according to claim 4, wherein is a monovalent hydrocarbon group having 13 to 32 carbon atoms, which may be linear, branched, or cyclic, or a combination thereof.

6. The hydrocarbon terminal group-containing compound according to claim 4, wherein k1 in the formula (1) is 2 or 3.

7. In the above formula (1), R 1 But the following formula (In the formula, R A represents a monovalent hydrocarbon group having 3 to 32 carbon atoms, which may be linear, branched, or cyclic, or a combination thereof; Q independently represents an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, a carbonyl (ketone) group, an ester group, a carbonate group, a sulfinyl group, a sulfonyl group, a thioester group, a thiocarbonate group, a thiocarbamate group, an amino group, an amide group, or a carbamate group. , a urea group, and a divalent nitrogen-containing heterocyclic group; Q' are independently a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, and a trivalent nitrogen-containing heterocyclic group; Q" are independently a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, and a linear trivalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent organopolysiloxane residue having 3 to 10 silicon atoms; R B are independently a single bond or a divalent hydrocarbon group having 1 to 32 carbon atoms, which may be linear, branched, or cyclic; R C are independently R A or a hydrogen atom, and p is an integer of 0 to 10. However, the total number of carbon atoms in each structure is 32 or less.

8. The hydrocarbon terminal group-containing compound according to claim 4, wherein in the above formula (1), Y is selected from the group consisting of alkylene groups having 1 to 20 carbon atoms which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms; alkylene groups having 1 to 10 carbon atoms which contain an arylene group having 6 to 8 carbon atoms; divalent groups in which alkylene groups having 1 to 8 carbon atoms are bonded to each other via a diorganosilylene group, a silalkylene structure, a silarylene structure, or a nitrogen-containing heterocyclic group; and divalent groups in which an alkylene group having 1 to 10 carbon atoms is bonded to a bond of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms.

9. In the above formula (1), Z is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, or —SiR 3 = (R 3 represents a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), 4 = (R 4 is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms), a trivalent to octavalent group selected from the group consisting of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent to octavalent nitrogen-containing heterocyclic group.

10. The hydrocarbon terminal group-containing compound according to claim 4, wherein in the above formula (1), U is a trivalent or tetravalent group selected from the group consisting of a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear trivalent or tetravalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent or tetravalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent or tetravalent nitrogen-containing heterocyclic group.

11. A surface treatment agent comprising the hydrocarbon terminal group-containing compound according to any one of claims 1 to 10 and / or its partial hydrolysis condensate.

12. An article surface-treated with the surface treatment agent according to claim 11.

13. A method for forming a coating comprising applying a surface treatment agent to a substrate, wherein the surface treatment agent contains a non-fluorine-based hydrocarbon terminal group-containing compound and / or a partial hydrolysis condensate thereof, which has at least one linear, branched, or cyclic monovalent hydrocarbon terminal group having 3 to 60 carbon atoms and further has at least one reactive silazane group.

14. The method for forming a coating according to claim 13, wherein the hydrocarbon end group of the hydrocarbon end group-containing compound is a group selected from an alkyl group having 6 to 28 carbon atoms and an aryl group having 6 to 32 carbon atoms.

15. The method for forming a coating according to claim 13, wherein the hydrocarbon terminal group-containing compound has two or more hydrocarbon terminal groups and a trivalent or higher linking group between the hydrocarbon terminal group and the reactive silazane group.

16. The hydrocarbon terminal group-containing compound is represented by the following general formula (1): (In the formula, R 1 are monovalent hydrocarbon groups having 3 to 32 carbon atoms, which may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which may be linear, branched, or cyclic, or a combination thereof; R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group; V independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom; Z independently represents a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group; Y independently represents a single bond or a divalent hydrocarbon group which may contain at least one atom selected from an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom; and A independently represents a group represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, n" is a number from 0 to 3, n'" is an integer from 0 to 2, the sum of n" and n'" is a number of 3 or less, and n' is (3-(n"+n'")) / 2), k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is 1 or 2, k1+k2+k3 is 2, 3, or 4, and m is an integer from 1 to 7.

17. The method for forming a coating according to claim 13, wherein the water contact angle of the coating on the surface of the substrate 30 minutes after application of the surface treatment agent is 90° or more.

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