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

Abstract

A surface treatment agent containing a hydrocarbon-terminal-group-containing compound of the following formula makes it possible to form a cured film that is exceptional in water repellency, slipperiness, dirt removability, and abrasion resistance, particularly steel wool abrasion resistance and wet abrasion resistance. (R1 is a C12-80 monovalent hydrocarbon group that includes a C12 or higher monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group and does not contain a hydrocarbon branched structure, R2 is H, a halogen atom, a hydroxyl group, a siloxy group, an -OSi(CH3)3 group, an -OSi(C2H5)3 group, an amino group, an SH group, a monovalent hydrocarbon group, R1, -V-Z-(Y-A)m, or -Y-A, U is a single bond, C, or a trivalent or tetravalent organic group, V is a single bond or a divalent hydrocarbon group, Z is a single bond, C, Si, N, S, or a trivalent to octavalent organic group, Y is a single bond or a divalent hydrocarbon group, A is a monovalent reactive group, k is 0, 1, or 2, and m is 1-7.)

Description

Hydrocarbon end group-containing compounds, surface treatment agents, cured coatings and articles

[0001] The present invention relates to a hydrocarbon terminal group-containing compound, and more particularly to a hydrocarbon terminal group-containing compound, particularly an alkyl terminal group-containing compound, that forms a coating film that is excellent in water repellency, slipperiness, dirt-wiping properties, and abrasion resistance; a surface treatment agent containing the compound; a cured coating film formed by the surface treatment agent; and an article having the cured coating.

[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. Materials that can meet these demands are highly desirable. Touch panel display surfaces are particularly susceptible to fingerprints, making the provision of a water- and oil-repellent layer desirable. 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 conspicuous.

[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] In particular, the compound disclosed in International Publication No. 2017 / 212850 (Patent Document 7) is said to have particularly excellent abrasion resistance, but it has been pointed out that due to its high water and oil repellency, fingerprints become conspicuous when they are left on the surface.

[0007] Therefore, WO 2019 / 82583 (Patent Document 8) proposes a surface treatment agent that does not use a fluorine group and suppresses fingerprint repelling. However, the abrasion resistance of the surface treatment agent is not sufficient to withstand harsh usage environments.

[0008] Furthermore, since fluorine-based compounds are difficult to decompose in nature and tend to accumulate in nature, there has been a demand for the development of surface protective agents for non-fluorine-based materials.

[0009] Japanese Patent Publication No. 2008-534696 Japanese Patent Publication No. 2008-537557 Japanese Patent Application Laid-Open No. 2012-072272 Japanese Patent Application Laid-Open No. 2012-157856 Japanese Patent Application Laid-Open No. 2013-136833 Japanese Patent Application Laid-Open No. 2015-199906 International Publication No. 2017 / 212850 International Publication No. 2019 / 82583

[0010] The present invention has been made in view of the above circumstances, and aims to provide a non-fluorine-based (i.e., no fluorine atoms in the molecule) hydrocarbon terminal group-containing compound capable of forming a cured coating that is excellent in water repellency, slipperiness, dirt wipeability, and abrasion resistance; a substantially non-fluorine-based surface treatment agent containing the compound; a cured coating formed by the surface treatment agent; and an article having the cured coating.

[0011] As a result of intensive research to achieve the above object, the present inventors have found that by using a hydrocarbon terminal group-containing compound having a partial structure consisting solely of carbon atoms and hydrogen atoms continuously bonded to a predetermined number of carbon atoms or more (12 or more carbon atoms) in the molecule (i.e., a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms), specifically a hydrocarbon terminal group-containing compound represented by general formula (1) described below, as a surface protective agent for the above non-fluorinated material, a surface treatment agent containing the compound can form a cured coating that is excellent in water repellency, slipperiness, dirt wiping ability, and abrasion resistance, particularly steel wool abrasion resistance and wet abrasion resistance, thereby completing the present invention.

[0012] Accordingly, the present invention provides the following hydrocarbon terminal group-containing compound, surface treatment agent, cured coating film, and article: [1] A compound represented by the following general formula (1): (In the formula, R 1 is a monovalent hydrocarbon group having 12 to 80 carbon atoms and containing no branched hydrocarbon structure, and which may contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms; R 2 are independently a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a —OSi(CH3)3 group, a —OSi(C2H5)3 group, an amino group, a thiol group, a monovalent hydrocarbon group having 1 or 2 carbon atoms, R 1 , -VZ-(Y-A)m or -Y-A, wherein U is a single bond, a carbon atom, or a trivalent or tetravalent organic group, V is a single bond or a divalent hydrocarbon group which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms, Z is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a trivalent to octavalent organic group, Y is independently a single bond or a divalent hydrocarbon group which may contain at least one atom selected from oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms, A is independently a monovalent reactive group, k is 0, 1, or 2, and m is an integer of 1 to 7. [2] A hydrocarbon terminal group-containing compound represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3), or the following general formula (3): (wherein n" is a number from 0 to 3, and n' is (3-n") / 2). [3] The hydrocarbon terminal group-containing compound according to [1], wherein R 1 is expressed by the following formula (4): (In the formula, R A is a monovalent hydrocarbon group having 3 to 80 carbon atoms, which is linear, cyclic, or a combination thereof; Q is independently a divalent group selected from the group consisting of an oxygen atom, a sulfur atom, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear divalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic divalent 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, and a divalent nitrogen-containing heterocyclic group; R B are independently a single bond, or a divalent hydrocarbon group having 1 to 70 carbon atoms which is linear, cyclic, or a combination thereof, and p is an integer of 0 to 10. A , R B is a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, and p is an integer of 2 to 10, then R Bis not a single bond, and the total number of carbon atoms in the above formula (4) is 12 to 80. [4] The hydrocarbon terminal group-containing compound according to any of [1] to [3], wherein in the above formula (1), Y is a single bond or a group 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 12 carbon atoms which contains 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 12 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. [5] In the above formula (1), Z is a single bond, or a carbon atom, a silicon atom, a nitrogen atom, a sulfur 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 The hydrocarbon terminal group-containing compound according to any one of [1] to [4], wherein U is a trivalent group represented by the formula (1) (wherein R 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 and having a valence of 3 to 8, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent to octavalent nitrogen-containing heterocyclic group. [6] The hydrocarbon terminal group-containing compound according to any one of [1] to [5], wherein U in the formula (1) is a single bond, or a trivalent or tetravalent group selected from the group consisting of a carbon atom and a trivalent or tetravalent cyclic hydrocarbon group having 5 to 8 carbon atoms. [7] The hydrocarbon terminal group-containing compound according to any one of [1] to [5], wherein R in the formula (1) is a trivalent group represented by the formula (1) (wherein R 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 and having a valence of 3 to 8, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent to octavalent nitrogen-containing heterocyclic group. 2is a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a —OSi(CH3)3 group, a —OSi(C2H5)3 group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms. [8] The hydrocarbon terminal group-containing compound according to any of [2] to [7], wherein in the above formula (2), X is selected from the group consisting of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen group, and a dialkylamino group having 2 to 10 carbon atoms. [9] A surface treatment agent comprising the hydrocarbon terminal group-containing compound according to any of [1] to [8].

[10] A cured coating formed by the surface treatment agent according to [9].

[11] An article having the cured coating according to

[10] .

[12] The article according to

[11] , characterized in that the water contact angle after steel wool abrasion described under the following conditions is 75° or more. [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 Number of abrasions: 3,000 times

[13] The article according to

[11] or

[12] , characterized in that the water contact angle after wet abrasion described under the following conditions is 75° or more. [Wet abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2 Number of abrasion cycles: 1,000 cycles

[14] The article according to any one of

[11] to

[13] , characterized in that the coefficient of dynamic friction is 0.20 or less.

[0013] In the case of the hydrocarbon terminal group-containing compound of the present invention, an article surface-treated with a surface treatment agent containing said compound has excellent water repellency, slipperiness, dirt wiping properties and abrasion resistance.

[0014] The hydrocarbon terminal group-containing compound of the present invention is represented by the following general formula (1). (In the formula, R 1is a monovalent hydrocarbon group having 12 to 80 carbon atoms and containing no branched hydrocarbon structure, and which may contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms; R 2 are independently a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a —OSi(CH3)3 group, a —OSi(C2H5)3 group, an amino group, a thiol group, a monovalent hydrocarbon group having 1 or 2 carbon atoms, R 1 , -VZ-(Y-A) m or -Y-A, wherein U is a single bond, a carbon atom, or a trivalent or tetravalent organic group, V is a single bond or a divalent hydrocarbon group which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms, Z is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a tri- to octavalent organic group, Y is independently a single bond or a divalent hydrocarbon group which may contain at least one atom selected from oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms, A is independently a monovalent reactive group, k is 0, 1, or 2, and m is an integer from 1 to 7.

[0015] The hydrocarbon terminal group-containing compound of the present invention has a structure in which it contains, at one molecular chain terminal, a monovalent or divalent, straight-chain, unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, which may contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon, a monovalent hydrocarbon group having 12 to 80 carbon atoms and which does not contain a branched hydrocarbon structure, and at the other molecular chain terminal, a reactive group that exhibits adhesion to substrates, these groups being linked via a linking group, and as a result, the cured coating of the surface treatment agent containing this compound is characterized by excellent water repellency, slip properties, dirt wipeability, and abrasion resistance.

[0016] In the above formula (1), R 1 contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, which may contain at least one atom selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom, and is a monovalent hydrocarbon group having 12 to 80 carbon atoms, preferably 12 to 60 carbon atoms, and more preferably 16 to 50 carbon atoms, which does not contain a branched hydrocarbon structure.

[0017] When at least one selected from oxygen atoms, sulfur atoms, nitrogen atoms, and silicon atoms is contained, it is preferable that the at least one selected from the group consisting of an ether group, a carbonyl (ketone) group, an ester group, a carbonate group, a thioether 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, an oxazole group, an imidazole group, a triazole group, a cyanurate group, an isocyanurate group, a diorganosilylene group, an organopolysiloxane residue, a silalkylene group, a silarylene group, or the like.

[0018] R 1 can be expressed by the following formula, for example. (In the formula, R A is a monovalent hydrocarbon group having 3 to 80 carbon atoms, which is linear, cyclic, or a combination thereof; Q is independently a divalent group selected from the group consisting of an oxygen atom, a sulfur atom, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear divalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic divalent 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, and a divalent nitrogen-containing heterocyclic group; R B are independently a single bond, or a divalent hydrocarbon group having 1 to 70 carbon atoms which is linear, cyclic, or a combination thereof, and p is an integer of 0 to 10. A , R B is a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, and p is an integer of 2 to 10 (i.e., -QR B - When the unit is repeated, R B is not a single bond, and the total number of carbon atoms in the above formula (4) is 12 to 80.

[0019] In the above formula (4), R Ais a monovalent hydrocarbon group having 3 to 80 carbon atoms, preferably 6 to 60 carbon atoms, and more preferably 12 to 50 carbon atoms, which is linear, cyclic, or a combination thereof, and does not have a branched structure.

[0020] R A Examples of such materials include the following: (In the formula, x is an integer of 2 to 79, preferably 5 to 59, and more preferably 11 to 49, and y is independently an integer of 1 or more, and the total number of carbon atoms in each structure is an integer of 80 or less.)

[0021] In the above formula (4), Q independently represents a divalent group selected from the group consisting of an oxygen atom, a sulfur atom, 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 RA and (if p is 2 or more, R B 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 (4), R B are independently a single bond, or a divalent hydrocarbon group which is linear, cyclic, or a combination thereof and has 1 to 70 carbon atoms, preferably 1 to 50 carbon atoms, and more preferably 1 to 30 carbon atoms, and does not have a branched structure.

[0025] R B Examples of such materials include the following: (In the formula, z is an integer of 1 or more, and the total number of carbon atoms in each structure is an integer of 70 or less. However, R A is a monovalent hydrocarbon group having 12 or less carbon atoms, z is an integer of 12 or more.

[0026] In the above formula (4), p is an integer of 0 to 10, and is preferably 0, 1 or 2.

[0027] However, in the above formula (4), R A , R B At least one of the above R A is a monovalent, linear, unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms. If the number of carbon atoms in the monovalent or divalent, linear, unsubstituted aliphatic saturated hydrocarbon group is less than 12, the intermolecular force between the linear, unsubstituted aliphatic saturated hydrocarbon chains of adjacent compounds during coating formation will be weak, resulting in reduced durability, such as abrasion resistance, of the coating that is formed. Furthermore, the total number of carbon atoms in the above formula (4) is 12 to 80, preferably 12 to 60, and more preferably 16 to 50.

[0028] Such an R 1 As the solvent, the following are preferably used. (In the formula, x, y, z, e, and f are the same as above, and the total number of carbon atoms in each structure is an integer of 80 or less, with the proviso that each structure contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0029] In the above formula (1), R 2 are independently a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a —OSi(CH3)3 group, a —OSi(C2H5)3 group, an amino group, a thiol group, a monovalent hydrocarbon group having 1 or 2 carbon atoms, R 1 , -VZ-(Y-A) m or -YA, and preferably a monovalent hydrocarbon group having 1 or 2 carbon atoms such as a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a -OSi(CH3)3 group, a -OSi(C2H5)3 group, an amino group, a thiol group, a methyl group, or an ethyl group. 2 It is preferred that at least one of is other than a hydrogen atom.

[0030] In the above formula (1), U represents a single bond, a carbon atom, or a trivalent or tetravalent organic group, and the trivalent or tetravalent organic group is preferably a trivalent or tetravalent cyclic hydrocarbon group having 5 to 8 carbon atoms.

[0031] Examples of U include the following, in addition to a single bond. In the following structure, the bond on the left side is R 1 The bond on the right is V and the other bonds are R 2 It is preferred to combine with

[0032] In the above formula (1), V is a single bond or a divalent hydrocarbon group preferably 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 U and Z are single bonds, V is preferably a single bond.

[0033] Specific examples of the divalent hydrocarbon group include alkylene groups having 1 to 10 carbon atoms, which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms, particularly straight-chain alkylene groups, and alkylene groups having 1 to 10 carbon atoms including arylene groups having 6 to 8 carbon atoms, particularly straight-chain alkylene groups (for example, alkylene / arylene groups having 7 to 18 carbon atoms).

[0034] 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.)

[0035] In the above formula (1), Z is 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).

[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 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.)

[0038] 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 oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms, 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 12 carbon atoms, which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms, alkylene groups having 1 to 12 carbon atoms, particularly linear alkylene groups, alkylene groups having 1 to 12 carbon atoms including arylene groups having 6 to 8 carbon atoms, particularly linear alkylene groups (e.g., alkylene-arylene groups having 7 to 18 carbon atoms), alkylene groups having 1 to 8 carbon atoms, particularly linear alkylene groups, Examples include divalent groups in which the groups 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 12 carbon atoms, particularly a straight-chain alkylene group, 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.

[0039] 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.

[0040] 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. (In the formula, a is independently 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.)

[0041] In the above formula (1), A's are independently monovalent reactive groups, preferably functional groups that have adhesion (bonding) reactivity to the surface of substrates made of various materials, such as paper, cloth, metals and their oxides, glass, plastics (resins), ceramics, quartz, etc., which are the target of surface treatment. Examples of monovalent reactive groups include monovalent groups selected from carbon-carbon double bond-containing groups (limited to groups involved in ionic addition polymerization or curing reactions with active energy rays (light), excluding alkenyl groups (groups that undergo hydrosilylation addition polymerization)), carbon-carbon triple bond-containing groups, cyclic ether groups, hydroxyl group-containing groups (excluding those consisting only of hydroxyl groups), thiol groups, amino groups, azide groups, nitrogen-containing heterocyclic groups, phosphate-containing groups, hydroxyl group-containing silyl groups (silanol groups), and hydrolyzable silyl groups.

[0042] Examples of A include carbon-carbon double bond-containing groups such as cinnamic acid group, sorbic acid group, acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, acrylamide group, methacrylamide group, and vinyl ether group; carbon-carbon triple bond-containing groups such as alkynyl groups having 2 to 20 carbon atoms, such as ethynyl group, propargyl group, 2-methyl-2-propynyl group, 3-butynyl group, 4-pentynyl group, and 5-hexynyl group; and propargyloxy group, 2-methyl-2-propynyloxy group, 3-butynyloxy group, 4-pentynyloxy group, and 5-hexynyl group. Examples of the alkyl group include alkynyloxy groups having 2 to 20 carbon atoms, such as hexynyloxy groups; cyclic ether groups such as epoxy groups, glycidyl groups, alicyclic epoxy groups, and oxetanyl groups; hydroxyl group-containing groups such as carboxyl groups and catechol groups; thiol groups; amino groups, alkylamino groups, and dialkylamino groups; azide groups; nitrogen-containing heterocyclic groups such as imidazolyl groups, triazolyl groups, benzotriazolyl groups, tetrazolyl groups, and isocyanate groups; phosphate-containing groups such as phosphate groups and phosphate ester groups; and monovalent groups such as hydroxyl group-containing silyl groups (silanol groups) and hydrolyzable silyl groups. Among these, hydroxyl group-containing silyl groups (silanol groups) and hydrolyzable silyl groups are preferred.

[0043] The hydroxyl group-containing silyl group and the hydrolyzable silyl group are those represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3), or the following general formula (3): (wherein n" is a number from 0 to 3, and n' is (3-n") / 2) is preferred.

[0044] In the above formula (2), R independently represents an alkyl group having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, a propyl group, or a butyl group, or a phenyl group, with a methyl group being preferred.

[0045] In the above formula (2), X is independently a hydroxyl group or a hydrolyzable group. Examples of X include hydroxyl groups; alkoxy groups having 1 to 10 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, and butoxy; alkoxyalkoxy groups having 2 to 10 carbon atoms, such as methoxymethoxy and methoxyethoxy; acyloxy groups having 1 to 10 carbon atoms, such as acetoxy; alkenyloxy groups having 2 to 10 carbon atoms, such as isopropenoxy and cyclopentenyloxy; halogen groups, such as chlorine, bromine, and iodo; and dialkylamino groups having 2 to 10 carbon atoms, such as dimethylamino and diethylamino. Among these, methoxy, ethoxy, isopropenoxy, and chlorine groups are preferred. X may be the same or different.

[0046] In the above formula (3), 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. When n"=3 in the above formula (3), the above general formula (1) represents the molecular formula (structural formula) of a hydrocarbon terminal group-containing compound (monomer), and when n"<3 in the above formula (3), the above general formula (1) represents the composition formula of a polymer of a hydrocarbon terminal group-containing compound (polysilazane compound).

[0047] In the above formula (3), n' is (3-n'') / 2, and is preferably 1.5.

[0048] In the above formula (1), k is 0, 1 or 2, i.e., 0 when U is a single bond, 1 when U is trivalent, and 2 when U is tetravalent. 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, k, and m, several hydrocarbon end group-containing compounds can be obtained. (In the formula, x, y, z, q, r, s, a, b, c, d, e, and f are each independently the same as above, provided that each structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0050] The hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention can be prepared, for example, by 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 hydrolyzable silyl group are mixed, and the mixture is subjected to a hydrosilylation addition reaction in the presence of a hydrosilylation reaction catalyst, thereby producing a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a hydrolyzable silyl group at its terminal). When a compound having a SiH group and a hydrolyzable silyl group in which the hydrolyzable group is a halogen group is used, the substituent (halogen atom) on the silyl group can then be converted to another hydrolyzable group.

[0051] Examples of hydrocarbon terminal group-containing compounds having an alkenyl group at the end include compounds represented by the following formulas (1A-1) and (1A-2). [In the formula, R 1 , R 2 , U, V, Z, k, m are the same as above. 1 ´ is the following formula (In the formula, R A , Q, R B is the same as above, and R A R' is a monovalent hydrocarbon group having 10 to 78 carbon atoms, which is linear, cyclic, or a combination thereof, and which contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 10 or more carbon atoms; B p' is a single bond or a divalent hydrocarbon group having 1 to 68 carbon atoms which is linear, cyclic or a combination thereof, and p' is an integer of 0 to 9. A , R B at least one of R is a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, or R B When p' is a divalent, linear, unsubstituted, aliphatic saturated hydrocarbon group having 10 or more carbon atoms and p' is an integer of 2 to 9 (i.e., -QR B - When the unit is repeated, R B is not a single bond, and the total number of carbon atoms in each structure is 10 to 78. 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.

[0052] In the above formula (1A-1), R 1 ' is any group represented by the above formula.

[0053] Here, in the above formula, R A ' is a monovalent hydrocarbon group having 10 to 78 carbon atoms, preferably 10 to 58 carbon atoms, more preferably 10 to 48 carbon atoms, which is linear, cyclic, or a combination thereof and has a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 10 or more carbon atoms and does not have a branched structure.

[0054] R AExamples of the ' include the following: (In the formula, y is the same as above, x' is an integer of 9 to 77, preferably 9 to 57, and more preferably 10 to 47, and y' is an integer of 0 or greater, such that the total number of carbon atoms in each structure is 78 or less. However, in each structure, y is 11 or greater, or y' is 10 or greater.)

[0055] In addition, in the above formula, R B ' is a single bond, or a divalent hydrocarbon group which is linear, cyclic, or a combination thereof and has 1 to 68 carbon atoms, preferably 1 to 48 carbon atoms, and more preferably 1 to 28 carbon atoms, and does not have a branched structure.

[0056] R B Examples of ' include the following, in addition to a single bond. (In the formula, z' is an integer of 1 or more, and the total number of carbon atoms in each structure is an integer of 68 or less. However, R A , R B When all of are monovalent hydrocarbon groups having 12 or less carbon atoms, z' is an integer of 10 or more.

[0057] In the above formula, p' is an integer of 0 to 9, and is preferably 0 or 1.

[0058] However, in the above formula, R A , R B at least one of R is a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, or R B When p' is an integer of 1 to 9, R B is not a single bond. The total number of carbon atoms in the above formula is 10 to 78, preferably 10 to 58, and more preferably 14 to 48.

[0059] R 1 Examples of the ' include the following: (In the formula, x, z, and z' are each independently the same as above, and are integers such that the total number of carbon atoms in each structure is 78 or less. However, in each structure, x is 11 or more, z is 12 or more, or z' is 10 or more.)

[0060] Examples of the compound represented by formula (1A-1) include the compounds shown below. (In the formula, x, z, and z' are each independently the same as above. However, in each structure, x is 11 or more, z is 12 or more, or z' is 10 or more.)

[0061] In the above formula (1A-2), Y 1 are each independently a single bond or a divalent hydrocarbon group preferably having 1 to 18 carbon atoms, which may contain at least one atom selected from oxygen, nitrogen, sulfur, and silicon atoms, and examples of groups other than single bonds 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.)

[0062] Examples of the compound represented by formula (1A-2) include the compounds shown below. (In the formula, x, z, q, a, a', b, c, and c' are each independently the same as above, provided that each structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0063] Examples of compounds having a SiH group and a hydrolyzable silyl group include trimethoxysilane, triethoxysilane, triacetoxysilane, and trichlorosilane.

[0064] In Preparation Method 1, the amount of the compound having a SiH group and a hydrolyzable silyl 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.

[0065] 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, particularly 0.01 to 100 ppm, calculated as transition metal (by mass) relative to the mass of the compound containing a hydrocarbon terminal group having an alkenyl group at its terminal.

[0066] 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 preferably 0 to 1,000 parts by mass, and particularly preferably 50 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0067] 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 a SiH group and a hydrolyzable silyl group are preferably a temperature of 20 to 120°C, particularly 60 to 100°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0068] In Preparation Method 1, when a compound having a SiH group and a hydrolyzable silyl group, such as trichlorosilane, in which the hydrolyzable group is a halogen group (a compound containing a SiH group and a halogenated silyl group) is used, the substituent (halogen atom) on the silyl group can then be converted to another hydrolyzable group, for example, an alkoxy group such as a methoxy group. Examples of compounds that can be used to convert the substituent (halogen atom) on the silyl group to another hydrolyzable group include methanol, ethanol, isopropanol, ethylene glycol monomethyl ether, and trimethyl orthoformate. The amount used is preferably 3 to 9 moles, and particularly 3 to 5 moles, per mole of halogen atom in the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal and the SiH group and a halogenated silyl group-containing compound.

[0069] In Preparation Method 1, the reaction conditions for converting a substituent (halogen atom) on a silyl group to another hydrolyzable group are preferably a temperature of 0 to 80°C, particularly 20 to 60°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0070] 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 a reactive group such as an alkenyl group and a hydrolyzable silyl group, and the mixture is subjected to a hydrosilylation addition reaction in the presence of a hydrosilylation reaction catalyst, thereby producing a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a terminal hydrolyzable silyl group).

[0071] 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, k, m are the same as above. 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; Y 2are independently a monovalent hydrocarbon group having a silicon atom or a siloxane bond and a terminal SiH group.

[0072] 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.)

[0073] 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, provided that each structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0074] 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, a is an integer of 1 to 10, 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.)

[0075] 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, provided that the structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0076] Among compounds having reactive groups such as an alkenyl group and a hydrolyzable silyl group, examples of the compound having an alkenyl group and a hydrolyzable silyl group include vinyltrimethoxysilane, allyltrimethoxysilane, octenyltrimethoxysilane, etc. Furthermore, examples of the compound having a reactive group other than an alkenyl group and a hydrolyzable silyl group include allyl glycidyl ether, etc.

[0077] In Preparation Method 2, the amount of the compound having a reactive group such as an alkenyl group or a hydrolyzable silyl 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.

[0078] In Preparation Method 2, the hydrosilylation catalyst can be exemplified by the same hydrosilylation catalysts 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, particularly 0.01 to 100 ppm, calculated as transition metal (by mass), relative to the mass of the hydrocarbon terminal group-containing compound having a terminal SiH group.

[0079] A solvent can be used during the reaction in Preparation Method 2. 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 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a terminal SiH group.

[0080] In Preparation Method 2, the reaction conditions are preferably a temperature of 20 to 120°C, particularly 60 to 100°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0081] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following: [Preparation Method 3] A hydrocarbon terminal group-containing compound having an alkenyl group at its terminal is mixed with trichlorosilane, reacted in the presence of a hydrosilylation reaction catalyst, and then the resulting compound is 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 that is a polymer thereof).

[0082] Here, the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the end and trichlorosilane can be prepared in the same manner as in Preparation Method 1.

[0083] In Preparation Method 3, the amount of ammonia gas used is preferably 1 to 300 cc / min, and particularly preferably 30 to 200 cc / min.

[0084] In Preparation Method 3, the reaction conditions for the reaction of ammonia gas with a reactant of a hydrocarbon terminal group-containing compound having an alkenyl group at its terminal and trichlorosilane 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.

[0085] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following. [Preparation Method 4] A hydrocarbon terminal group-containing compound having a terminal hydroxyl group is mixed with a compound having an isocyanate group and a reactive group (e.g., a hydrolyzable silyl group or a (meth)acryloyloxy group), and the mixture is reacted in the presence of a catalyst to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a reactive group such as a hydrolyzable silyl group or a (meth)acryloyloxy group at the terminal via a urethane bond). In the present invention, the (meth)acryloyloxy group refers to an acryloyloxy group or a methacryloyloxy group.

[0086] Examples of the hydrocarbon terminal group-containing compound having a hydroxyl group at the end include compounds represented by the following formula (1D) or (1E). (In the formula, R 1 , R 2 , U, V, Z, k, m, b are the same as above. 1 is a divalent hydrocarbon group having 1 to 10 carbon atoms.

[0087] Examples of the compound represented by formula (1D) include the compounds shown below. (In the formula, x, z, and b are each independently the same as above, provided that each structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0088] In the above formula (1E), V1 is a divalent hydrocarbon group having 1 to 10 carbon atoms, preferably an alkylene group, and examples thereof include those shown below. (wherein q is the same as above.)

[0089] Examples of the compound represented by formula (1E) include the compounds shown below. (In the formula, x, z, and q are each independently the same as above, with the proviso that the structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0090] Examples of compounds having an isocyanate group and a reactive group include (3-isocyanatopropyl)trimethoxysilane, (3-isocyanatopropyl)triethoxysilane, and 1,1-(bisacryloyloxymethyl)ethyl isocyanate.

[0091] In Preparation Method 4, the amount of the compound having an isocyanate group and a reactive group used is preferably 1 to 3 moles, particularly 1 to 1.5 moles, per mole of hydroxyl group in the hydrocarbon terminal group-containing compound having a terminal hydroxyl group.

[0092] In Preparation Method 4, examples of the catalyst include titanium compounds such as titanium tetra-2-ethylhexoxide, tetra n-butyl titanate, and tetra n-propyl titanate; zirconium compounds such as tetra n-butyl zirconate and tetra n-propyl zirconate; tin compounds such as dibutyltin dimethoxide and dibutyltin dilaurate; bismuth compounds such as bismuth tris(2-ethylhexanoate); and amine catalysts such as diazabicycloundecene. The amount of catalyst used is preferably 0.01 to 100 parts by mass, and particularly preferably 0.1 to 20 parts by mass, per 100 parts by mass of the compound containing a hydrocarbon terminal group having a terminal hydroxyl group.

[0093] A solvent can be used during the reaction in Preparation Method 4. 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 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a terminal hydroxyl group.

[0094] In Preparation Method 4, the reaction conditions are preferably a temperature of 20 to 100° C., particularly 30 to 60° C., and a time of 0.5 to 72 hours, particularly 1 to 36 hours.

[0095] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following: [Preparation Method 5] A hydrocarbon terminal group-containing compound having a terminal hydroxyl group is mixed with phosphorus oxychloride to cause a reaction, and then water is added to cause a reaction to occur, thereby producing a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a reactive group such as a phosphate group at the terminal).

[0096] Here, examples of the hydrocarbon terminal group-containing compound having a terminal hydroxyl group include the same compounds as those represented by formula (1D) in Preparation Method 4 above.

[0097] In Preparation Method 5, the amount of phosphorus oxychloride used is preferably 1 to 4 moles, particularly 1 to 2 moles, per mole of hydroxyl group in the hydrocarbon terminal group-containing compound having a terminal hydroxyl group.

[0098] In Preparation Method 5, a solvent can be used when reacting the hydrocarbon terminal group-containing compound having a terminal hydroxyl group with phosphorus oxychloride. Examples of the solvent include the same solvents as those used in Preparation Method 1. The amount of solvent used is preferably 0 to 1,000 parts by mass, and more preferably 50 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a terminal hydroxyl group.

[0099] In Preparation Method 5, the reaction conditions for the hydrocarbon terminal group-containing compound having a terminal hydroxyl group with phosphorus oxychloride are preferably a temperature of 0 to 80°C, particularly 15 to 50°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0100] In Preparation Method 5, the amount of water used is preferably 50 to 1,000 parts by mass, and particularly preferably 100 to 500 parts by mass, per 100 parts by mass of the compound containing a hydrocarbon terminal group having a terminal hydroxyl group.

[0101] In Preparation Method 5, the reaction conditions for the reaction of water with the reaction product of a hydrocarbon terminal group-containing compound having a terminal hydroxyl group and phosphorus oxychloride are preferably a temperature of 0 to 80°C, particularly 15 to 50°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0102] Alternatively, as an alternative method [Preparation Method 5'], a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a reactive group such as a phosphate ester group at the terminal) can be produced by mixing and reacting a hydrocarbon terminal group-containing compound having a leaving group at the terminal with a trialkyl phosphite.

[0103] Here, examples of the hydrocarbon terminal group-containing compound having a leaving group at the end include the same compounds as those represented by (1G) and (1H) in Preparation Method 8 described below.

[0104] In [Preparation Method 5'], examples of trialkyl phosphite include trimethyl phosphite, triethyl phosphite, etc. The amount of trialkyl phosphite used is preferably 1 to 8 moles, particularly 1 to 4 moles, per mole of leaving group in the hydrocarbon terminal group-containing compound having a leaving group at the terminal.

[0105] In Preparation Method 5', a solvent can be used when reacting a hydrocarbon terminal group-containing compound having a terminal leaving group with a trialkyl phosphite. Examples of the solvent include the same solvents as those used in Preparation Method 1. The amount of solvent used is preferably 0 to 1,000 parts by mass, and more preferably 0 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a terminal leaving group.

[0106] In [Preparation Method 5'], the reaction conditions for the hydrocarbon terminal group-containing compound having a terminal leaving group with trialkyl phosphite are preferably a temperature of 25 to 160°C, particularly 80 to 140°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0107] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following: [Preparation Method 6] A hydrocarbon terminal group-containing compound having an NH group at its terminal is mixed with a compound having an isocyanate group and a reactive group (e.g., a hydrolyzable silyl group, a (meth)acryloyloxy group, etc.) and reacted to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a reactive group such as a hydrolyzable silyl group or a (meth)acryloyloxy group at its terminal via a urea bond).

[0108] Examples of hydrocarbon end group-containing compounds having an NH2 group at the end include the following: (In the formula, x, z, and b are each independently the same as above, provided that each structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0109] Examples of compounds having an isocyanate group and a reactive group include (3-isocyanatopropyl)trimethoxysilane, (3-isocyanatopropyl)triethoxysilane, and 2-isocyanatoethyl methacrylate.

[0110] In Preparation Method 6, the amount of the compound having an isocyanate group and a reactive group used is preferably 1 to 3 moles, particularly 1 to 1.5 moles, per mole of the hydrocarbon terminal group-containing compound having an NH group at the terminal.

[0111] A solvent can be used during the reaction in Preparation Method 6. Examples of the solvent include the same solvents as those used in Preparation Method 1. The amount of solvent used is preferably 0 to 1,000 parts by mass, and more preferably 50 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an NH group at its terminal.

[0112] In Preparation Method 6, the reaction conditions are preferably a temperature of 0 to 100°C, particularly 20 to 60°C, and a time of 0.5 to 72 hours, particularly 1 to 36 hours.

[0113] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following: [Preparation Method 7] A hydrocarbon terminal group-containing compound having an alkenyl group at its terminal is mixed with thioacetic acid and reacted in the presence of a polymerization initiator, and then the resulting compound having a thioester group is mixed with a hydrosilane compound and reacted in the presence of a Pd / C catalyst, followed by elimination of the silicon moiety on the sulfur atom, thereby producing a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a thiol group (mercapto group) at its terminal).

[0114] Here, examples of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal include the same compounds as those represented by formula (1A) in Preparation Method 1 above.

[0115] In Preparation Method 7, the amount of thioacetic acid used is preferably 1 to 5 moles, particularly 1 to 3 moles, per mole of alkenyl group in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0116] In Preparation Method 7, examples of the polymerization initiator include peroxide compounds such as azo compounds such as 2,2'-azobisisobutyronitrile, diacyl peroxides such as benzoyl peroxide and lauroyl peroxide, dialkyl peroxides such as dicumyl peroxide and di-tert-butyl peroxide, peroxycarbonates such as diisopropyl peroxydicarbonate and bis(4-tert-butylcyclohexyl)peroxydicarbonate, and alkyl peresters such as t-butyl peroxyoctoate and tert-butyl peroxybenzoate. The amount of the polymerization initiator used is preferably 0.01 to 3 mol, and particularly preferably 0.1 to 1.5 mol, per mol of alkenyl groups in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0117] In Preparation Method 7, the reaction conditions for the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with thioacetic acid are preferably a temperature of 20 to 100°C, particularly 40 to 80°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0118] In Preparation Method 7, examples of the hydrosilane compound include trialkylsilanes such as triethylsilane. The amount of the hydrosilane compound used is preferably 1 to 6 moles, particularly 1.5 to 4 moles, per mole of thioester group in the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at its terminal with thioacetic acid (compound having a thioester group).

[0119] In Preparation Method 7, the amount of Pd / C catalyst used is preferably an amount such that 0.001 to 1 mole, particularly 0.01 to 0.5 moles of Pd atoms are used per mole of thioester group in the reaction product (compound having a thioester group) of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with thioacetic acid.

[0120] In Preparation Method 7, the reaction conditions for the reaction of the hydrosilane compound with the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal and thioacetic acid (a compound having a thioester group) are preferably a temperature of 20 to 100°C, particularly 40 to 80°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0121] In Preparation Method 7, when the silicon moiety on the sulfur atom of the reaction product (compound having a silylthioether group) of a hydrosilane compound with a reaction product (compound having a thioester group) of a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with thioacetic acid is eliminated, the elimination can be carried out under acidic or alkaline conditions. Examples of the acid include hydrochloric acid and sulfuric acid, and examples of the alkali include sodium hydroxide. The acid or alkali may be diluted with water.

[0122] The amount of acid or alkali used is preferably 1 to 10 moles, particularly 1 to 5 moles, of the acid or base per mole of silyl thioether group in the reaction product (compound having a silyl thioether group) of a hydrosilane compound with a reaction product (compound having a thioester group) of a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with thioacetic acid.

[0123] In Preparation Method 7, the reaction conditions for eliminating the silicon moiety on the sulfur atom of the reaction product of a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal with thioacetic acid (a compound having a thioester group) and a hydrosilane compound (a compound having a silyl thioether group) are preferably a temperature of 20 to 100°C, particularly 40 to 80°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0124] In Preparation Method 7, 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 solvent used is preferably 0 to 1,000 parts by mass, and particularly preferably 50 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an alkenyl group at its terminal, or the reaction product of the hydrocarbon terminal group-containing compound having an alkenyl group at its terminal with thioacetic acid (compound having a thioester group).

[0125] Other methods for preparing the hydrocarbon terminal group-containing compound represented by general formula (1) of the present invention include the following: [Preparation Method 8] The hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having an amino group at its terminal) can be produced by reacting a hydrocarbon terminal group-containing compound having a leaving group (e.g., a halogen atom or a sulfonyl ester group) at its terminal with an amination reagent.

[0126] Examples of hydrocarbon terminal group-containing compounds having a leaving group at the end include compounds represented by the following formula (1G), (1H) or (1I). (In the formula, R 1 , R 2 ,U,V,V 1 , Z, k, m, and b are the same as above. X' is a halogen atom or a sulfonyl ester group.

[0127] Examples of the compound represented by formula (1G) include the compounds shown below. (In the formulae, x, z, and b are each independently the same as above, provided that each structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0128] Examples of the compound represented by formula (1H) include the compounds shown below. (wherein x, z, and q are the same as above, with the proviso that the structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0129] Examples of the compound represented by formula (1I) include the compounds shown below. (wherein x and z are the same as above, with the proviso that the structural formula contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms.)

[0130] Examples of the amination reagent include phthalimide, potassium phthalimide, and sodium phthalimide.

[0131] In Preparation Method 8, the amount of the amination reagent used is preferably 1 to 6 moles, particularly 1.5 to 3 moles, per mole of leaving group in the hydrocarbon terminal group-containing compound having a leaving group at the terminal.

[0132] In Preparation Method 8, a solvent can be used during the reaction. 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, ketones such as acetone and methyl ethyl ketone, amides such as dimethylformamide and dimethylacetamide, and alcohols such as methanol, ethanol, and isopropanol. The amount of the solvent used is preferably 0 to 1,000 parts by mass, and particularly preferably 50 to 300 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having a leaving group at the terminal.

[0133] In Preparation Method 8, the reaction conditions for the hydrocarbon terminal group-containing compound having a leaving group at the terminal with the amination reagent are preferably a temperature of 40 to 150°C, particularly 60 to 120°C, for 0.5 to 72 hours, particularly 1 to 36 hours.

[0134] In Preparation Method 8, if the amination reagent is protected, deprotection can be carried out. Examples of compounds that can be used for deprotection include hydrazine monohydrate. The amount of hydrazine monohydrate used is preferably 1 to 5 moles, particularly 1 to 3 moles, per mole of the protected amino group in the reaction product of the hydrocarbon terminal group-containing compound having a leaving group at the terminal and the amination reagent.

[0135] In Preparation Method 8, the reaction conditions for deprotection are preferably a temperature of 0 to 90° C., particularly 20 to 70° C., for 0.5 to 72 hours, particularly 1 to 36 hours.

[0136] The present invention further provides a substantially fluorine-free surface treatment agent containing a non-fluorine-containing (i.e., fluorine-free) hydrocarbon terminal group-containing compound represented by the above formula (1) as a main component. The surface treatment agent need only contain the hydrocarbon terminal group-containing compound represented by formula (1) as a main component, and may also contain unreacted raw materials or reaction intermediates prior to the introduction of the reactive group of the hydrocarbon terminal group-containing compound represented by formula (1). Furthermore, the surface treatment agent preferably uses a hydrocarbon terminal group-containing compound in which the reactive group is a hydroxyl-containing silyl group or a hydrolyzable silyl group, particularly a hydrolyzable silyl group. In this case, the surface treatment agent may contain a partial (hydrolyzed) condensate obtained by partially condensing the hydroxyl-containing silyl group or by partially hydrolyzing the hydrolyzable silyl group in advance using a known method. In this invention, the term "partial (hydrolyzed) condensate" refers to a partial condensate or a partial hydrolyzed condensate.

[0137] If necessary, the surface treatment agent may contain a hydrolysis 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 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) condensate).

[0138] 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.

[0139] 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 (hydrolyzed) condensate). The optimal concentration of the hydrocarbon terminal group-containing compound (and its partial (hydrolyzed) 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 (hydrolyzed) 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 (hydrolyzed) condensate). In either case, the amount of 100 parts by mass refers to the case where the coating is carried out directly without using a solvent.

[0140] 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 used 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.), curing is preferably performed at 25 to 200°C, particularly 25 to 150°C, for 30 minutes to 36 hours, particularly 1 to 24 hours. In the case of vapor deposition, curing is preferably performed at a temperature in the range of 20 to 200°C for 1 to 24 hours. Curing may also be performed under humidified conditions. For example, when using a hydrocarbon terminal group-containing compound having a hydrolyzable silyl group, spray coating can be performed by diluting the compound in an organic solvent containing water in advance and hydrolyzing the compound, i.e., generating Si—OH, before spray coating, thereby achieving rapid curing after coating.

[0141] 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.

[0142] 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, quartz, etc. SiO-treated glass and film are particularly preferred.

[0143] 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.

[0144] Examples of articles to be treated with the surface treatment agent of the present invention (articles having a cured coating of the surface treatment agent) include 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 equipment such as gastroscopes, copiers, PCs, liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflection films, and other optical articles and electronic components. 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.

[0145] 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.

[0146] 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. 1The film thickness was measured by spectroscopic ellipsometry using a spectroscopic ellipsometer. The room temperature was 23°C.

[0147] Synthesis Example 1 A reaction vessel was charged with a compound represented by the following formula (A): 1.00 g (2.96 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.08 g (8.87 × 10 -3 mol), and 1.13 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (3.49 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.28 g of a product.

[0148] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (B):

[0149] Synthesis Example 2 A reaction vessel was charged with a compound represented by the following formula (C): 1.00 g (2.38 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.872 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 was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.20 g of a product.

[0150] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (D):

[0151] Synthesis Example 3 A reaction vessel was charged with a compound represented by the following formula (E): 1.00 g (3.73 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.37 g (1.12 × 10-2 mol), and 1.42 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (4.40 x 10 as Pt alone) -8 The mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.38 g of a product.

[0152] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (F):

[0153] Synthesis Example 4 A reaction vessel was charged with a compound represented by the following formula (G): 1.00 g (2.23 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.63 g (1.34 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 8.52 × 10 -3 g (2.63 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.50 g of a product.

[0154] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (H):

[0155] Synthesis Example 5 A reaction vessel was charged with a compound represented by the following formula (I): 1.00 g (1.64 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.21 g (9.88 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 6.29 × 10 -3 g (1.94 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.35 g of a product.

[0156] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (J):

[0157] Synthesis Example 6 A reaction vessel was charged with a compound represented by the following formula (K): 1.00 g (2.13 × 10 -3 mol), toluene 1.00 g, trichlorosilane 0.867 g (6.41 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 8.15 × 10 -3 g (2.52 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.26 g of a product.

[0158] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (L):

[0159] Synthesis Example 7 A reaction vessel was charged with a compound represented by the following formula (M): 1.00 g (2.62 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.959 g (7.85 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 9.99 × 10 -3 g (3.09 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.27 g of a product.

[0160] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (N):

[0161] Synthesis Example 8 A reaction vessel was charged with a compound represented by the following formula (O): 1.00 g (1.65 × 10 -3 mol), toluene 2.00 g, allyltrimethoxysilane 1.60 g (9.88 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 6.29 × 10 -3 g (1.94 x 10 as Pt alone) -8The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.79 g of a product.

[0162] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (P):

[0163] Synthesis Example 9 A reaction vessel was charged with a compound represented by the following formula (Q): 1.00 g (3.22 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.18 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) -8 The mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.30 g of a product.

[0164] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (R):

[0165] Synthesis Example 10 A reaction vessel was charged with a compound represented by the following formula (S): 1.00 g (2.63 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.964 g (7.89 × 10 -3 mol), and 1.00 x 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (3.10 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.29 g of a product.

[0166] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (T):

[0167] Synthesis Example 11 A reaction vessel was charged with a compound represented by the following formula (U): 1.00 g (2.04 × 10-3 mol), toluene 1.00 g, trimethoxysilane 1.50 g (1.23 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.80 × 10 -3 g (2.41 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.47 g of a product.

[0168] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (V):

[0169] Synthesis Example 12 A reaction vessel was charged with a compound represented by the following formula (W): 1.00 g (2.10 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.54 g (1.26 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 8.03 × 10 -3 g (2.48 x 10 as Pt alone) -8 The mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.45 g of a product.

[0170] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (X):

[0171] Synthesis Example 13 A reaction vessel was charged with a compound represented by the following formula (Y): 1.00 g (2.11 × 10 -3 mol), toluene 1.00 g, vinyltrimethoxysilane 0.624 g (4.22 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 8.05 × 10 -3 g (2.49 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.26 g of a product.

[0172] The resulting compound is1 H-NMR confirmed that the compound had a structure represented by the following formula (Z):

[0173] Synthesis Example 14 A reaction vessel was charged with a compound represented by the following formula (AA): 1.00 g (2.04 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 2.24 g (1.84 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.79 × 10 -3 g (2.41 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.72 g of a product.

[0174] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AB):

[0175] Synthesis Example 15 A reaction vessel was charged with a compound represented by the following formula (AC): 1.00 g (2.87 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 2.10 g (1.72 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 1.10 × 10 -2 g (3.39 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.69 g of a product.

[0176] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AD):

[0177] Synthesis Example 16 A reaction vessel was charged with a compound represented by the following formula (AE): 1.00 g (1.91 × 10 -3 mol), toluene 1.00 g, triacetoxysilane 3.55 g (1.72 × 10 -2mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.31 × 10 -3 g (2.26 x 10 as Pt alone) -8 The mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 2.10 g of a product.

[0178] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AF):

[0179] Synthesis Example 17 A reaction vessel was charged with a compound represented by the following formula (AG): 1.00 g (2.54 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.929 g (7.61 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 9.69 × 10 -3 g (2.99 x 10 as Pt alone) -8 The mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.24 g of a product.

[0180] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AH):

[0181] Synthesis Example 18 A reaction vessel was charged with a compound represented by the following formula (AI): 1.00 g (1.55 × 10 -3 mol), toluene 2.00 g, octenyltrimethoxysilane 2.16 g (9.28 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 5.91 × 10 -3 g (1.83 x 10 as Pt alone) -8 The mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 2.02 g of a product.

[0182] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AJ):

[0183] Synthesis Example 19 A reaction vessel was charged with a compound represented by the following formula (AK): 1.00 g (2.18 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.800 g (6.55 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 8.33 × 10 -3 g (2.58 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.26 g of a product.

[0184] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AL):

[0185] Synthesis Example 20 A reaction vessel was charged with a compound represented by the following formula (AM): 1.00 g (1.89 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 2.08 g (1.70 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.23 × 10 -3 g (2.23 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.66 g of a product.

[0186] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AN):

[0187] Synthesis Example 21 A reaction vessel was charged with a compound represented by the following formula (AO): 1.00 g (2.45 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.80 g (1.47 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 9.38 × 10 -3 g (2.90 x 10 as Pt alone)-8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.59 g of a product.

[0188] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AP):

[0189] Synthesis Example 22 A reaction vessel was charged with a compound represented by the following formula (AQ): 1.00 g (2.77 × 10 -3 mol), toluene 1.00 g, trichlorosilane 1.12 g (8.30 × 10 -3 mol), and 1.06 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -3 g (3.27 x 10 as Pt alone) -8 The resulting mixture was aged at 60° C. for 24 hours. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure. The resulting product, 1.00 g of toluene, 7.02×10 ethylene glycol monomethyl ether, and 1.00 g of ethylene glycol monomethyl ether were mixed. -2 g (9.22 x 10 -4 mol) and aged at 50°C for 8 hours. -3 The resulting mixture was aged at room temperature for 24 hours, after which the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.29 g of a product.

[0190] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AR):

[0191] Synthesis Example 23 A reaction vessel was charged with a compound represented by the following formula (AS): 1.00 g (1.94 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.43 g (1.17 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.42 × 10 -3 g (2.29 x 10 as Pt alone) -8The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.42 g of a product.

[0192] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AT):

[0193] Synthesis Example 24 A reaction vessel was charged with a compound represented by the following formula (AU): 1.00 g (2.04 × 10 -3 mol), toluene 1.00 g, triethoxysilane 2.01 g (1.22 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.42 × 10 -3 g (2.29 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.60 g of a product.

[0194] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AV):

[0195] Synthesis Example 25 A reaction vessel was charged with a compound represented by the following formula (AW): 1.00 g (1.98 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 1.45 g (1.19 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 7.57 × 10 -3 g (2.34 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.42 g of a product.

[0196] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AX):

[0197] Synthesis Example 26 A reaction vessel was charged with a compound represented by the following formula (AY): 1.00 g (2.46 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.902 g (7.38 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 9.40 × 10 -3 g (2.90 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.28 g of a product.

[0198] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AZ):

[0199] Synthesis Example 27 A reaction vessel was charged with a compound represented by the following formula (BA): 1.00 g (2.64 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 0.966 g (7.91 × 10 -3 mol), and 1.01 × 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (3.11 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.31 g of a product.

[0200] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BB):

[0201] Synthesis Example 28 A reaction vessel was charged with a compound represented by the following formula (BC): 1.00 g (2.63 × 10 -3 mol), toluene 1.00 g, trichlorosilane 1.07 g (7.89 × 10 -3 mol), and 1.00 x 10 chloroplatinic acid / vinylsiloxane complex in toluene -2 g (3.10 x 10 as Pt alone) -8The 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.

[0202] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BD):

[0203] Synthesis Example 29 A reaction vessel was charged with a compound represented by the following formula (AW): 1.00 g (2.17 × 10 -3 mol), toluene 1.00 g, trimethoxysilane 2.39 g (1.95 × 10 -2 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 8.29 × 10 -3 g (2.56 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.78 g of a product.

[0204] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (AX):

[0205] Synthesis Example 30 A reaction vessel was charged with a compound represented by the following formula (BE): 1.00 g (2.32 × 10 -3 mol), toluene 1.00 g, (3-isocyanatopropyl)triethoxysilane 1.78 g (7.20 × 10 -3 mol), and titanium tetra-2-ethylhexoxide 6.56 × 10 -2 g (1.16 x 10 -4 The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 2.70 g of a product.

[0206] The resulting compound is 1H-NMR confirmed that the compound had a structure represented by the following formula (BF):

[0207] Synthesis Example 31 A reaction vessel was charged with a compound represented by the following formula (BG): 1.00 g (2.82 × 10 -3 mol), toluene 1.00 g, (3-isocyanatopropyl)trimethoxysilane 0.637 g (3.10 × 10 -3 mol), and titanium tetra-2-ethylhexoxide 7.97 × 10 -2 g (1.41 x 10 -4 The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.50 g of a product.

[0208] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BH):

[0209] Synthesis Example 32 A reaction vessel was charged with a compound represented by the following formula (BI): 1.00 g (2.13 × 10 -3 mol), toluene 1.00 g, (3-isocyanatopropyl)triethoxysilane 0.580 g (2.34 × 10 -3 The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.50 g of a product.

[0210] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BJ):

[0211] Synthesis Example 33 A reaction vessel was charged with a compound represented by the following formula (BK): 1.00 g (3.05 × 10 -3 mol), toluene 1.00 g, (3-isocyanatopropyl)trimethoxysilane 1.31 g (6.40 × 10 -3 mol), and titanium tetra-2-ethylhexoxide 8.60 × 10 -2 g (1.52 x 10 -4The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 2.22 g of a product.

[0212] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BL):

[0213] Synthesis Example 34 A reaction vessel was charged with a compound represented by the following formula (AX): 1.00 g (1.36 × 10 -3 mol), toluene 1.00 g, (3-isocyanatopropyl)trimethoxysilane 0.307 g (1.50 × 10 -3 mol), and titanium tetra-2-ethylhexoxide 3.84 × 10 -2 g (6.81 x 10 -5 The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.25 g of a product.

[0214] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BH):

[0215] Synthesis Example 35 A reaction vessel was charged with a compound represented by the following formula (BM): 1.00 g (2.28 × 10 -3 mol), toluene 1.00 g, phosphorus oxychloride 0.385 g (2.56 × 10 -3 The resulting mixture was mixed with 4.00 g of water and aged at room temperature for 8 hours. The resulting solution was then aged at room temperature for 1 hour. The aqueous layer was then removed by separation, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.30 g of product.

[0216] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BN):

[0217] Synthesis Example 36 A reaction vessel was charged with a compound represented by the following formula (BO): 1.00 g (2.37 × 10 -3mol), toluene 1.00 g, thioacetic acid 0.360 g (4.73 × 10 -3 mol), and 0.389 g (2.37 × 10 mol) of AIBN (2,2'-azobisisobutyronitrile) -3 mol) were mixed and aged at 70°C for 24 hours. 2.00 g of water was added to the obtained solution, and a separation operation was carried out, after which the solvent and unreacted materials were distilled off under reduced pressure. Subsequently, the obtained compound was mixed with 1.00 g of toluene and 0.826 g (7.10 x 10) of triethylsilane. -3 mol), and Pd / C 1.26×10 -2 g (1.18 x 10 as Pd alone) -4 The resulting solution was mixed with 2.00 g of 2 M hydrochloric acid and aged at 80° C. for 24 hours. The aqueous layer was then removed by separation, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 0.970 g of a product.

[0218] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BP):

[0219] Synthesis Example 37 A reaction vessel was charged with a compound represented by the following formula (BQ): 1.00 g (2.40 × 10 -3 mol), N,N-dimethylformamide (DMF) 2.00 g, potassium phthalimide 0.667 g (3.60 × 10 -3 mol) were mixed and aged at 110°C for 24 hours. Thereafter, 2.00 g of water was added to the obtained solution, and a separation operation was carried out, after which the solvent and unreacted materials were distilled off under reduced pressure. Subsequently, the obtained compound was mixed with 2.00 g of ethanol and 0.242 g (4.80 x 10 -3 The resulting mixture was mixed with 1.00 g of water and aged at 65° C. for 24 hours. 4.00 g of water was added to the resulting solution, and the mixture was aged at room temperature for 1 hour. After that, the aqueous layer was removed by a separation operation, and the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.04 g of a product.

[0220] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BR):

[0221] Synthesis Example 38 A reaction vessel was charged with a compound represented by the following formula (BS): 1.00 g (1.82 × 10 -3 mol), toluene 2.00 g, allyl glycidyl ether 1.04 g (9.09 × 10 -3 mol), and a toluene solution of chloroplatinic acid / vinylsiloxane complex 6.94 × 10 -3 g (2.15 x 10 as Pt alone) -8 The resulting mixture was aged for 24 hours at 80° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.58 g of a product.

[0222] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BT):

[0223] Synthesis Example 39 A reaction vessel was charged with a compound represented by the following formula (BU): 1.00 g (2.27 × 10 -3 mol), toluene 1.00 g, Karenz BEI (1,1-(bisacryloyloxymethyl)ethyl isocyanate) 0.570 g (2.38 × 10 -3 mol), and titanium tetra-2-ethylhexoxide 6.41 × 10 -2 g (1.14 x 10 -4 The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.53 g of a product.

[0224] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BV):

[0225] Synthesis Example 40 A reaction vessel was charged with a compound represented by the following formula (BW): 1.00 g (2.21 × 10 -3 mol), toluene 1.00 g, Karenz MOI (2-isocyanatoethyl methacrylate) 0.359 g (2.32 × 10 -3 The resulting mixture was aged for 24 hours at 50° C. Thereafter, the solvent and unreacted materials were distilled off under reduced pressure to obtain 1.30 g of a product.

[0226] The resulting compound is 1 H-NMR confirmed that the compound had a structure represented by the following formula (BX):

[0227] Example 1 The compound obtained in Synthesis Example 2 was dissolved in toluene to a concentration of 20% by mass to prepare a surface treatment agent.

[0228] Example 2 The compound obtained in Synthesis Example 4 was dissolved in isononane to a concentration of 20% by mass to prepare a surface treatment agent.

[0229] Example 3 The compound obtained in Synthesis Example 5 was dissolved in propylene glycol monomethyl ether acetate to a concentration of 20% by mass to prepare a surface treatment agent.

[0230] Example 4 The compound obtained in Synthesis Example 6 was dissolved in toluene to a concentration of 10% by mass to prepare a surface treatment agent.

[0231] Example 5 The compound obtained in Synthesis Example 8 was dissolved in butyl acetate to a concentration of 20% by mass to prepare a surface treatment agent.

[0232] Example 6 The compound obtained in Synthesis Example 11 was dissolved in propylene glycol monomethyl ether to a concentration of 10% by mass to prepare a surface treatment agent.

[0233] Example 7 The compound obtained in Synthesis Example 12 was dissolved in ethylcyclohexane to a concentration of 5% by mass to prepare a surface treatment agent.

[0234] 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.

[0235] Example 9 The compound obtained in Synthesis Example 16 was dissolved in toluene to a concentration of 90% by mass to prepare a surface treatment agent.

[0236] Example 10 The compound obtained in Synthesis Example 18 was dissolved in toluene to a concentration of 80% by mass to prepare a surface treatment agent.

[0237] Example 11 The compound obtained in Synthesis Example 20 was dissolved in dibutyl ether to a concentration of 10% by mass to prepare a surface treatment agent.

[0238] Example 12 The compound obtained in Synthesis Example 21 was dissolved in dibutyl ether to a concentration of 50% by mass to prepare a surface treatment agent.

[0239] Example 13 The compound obtained in Synthesis Example 22 was dissolved in a 20 / 80 hexane / isononane mixed solution to a concentration of 20% by mass to prepare a surface treatment agent.

[0240] Example 14 The compound obtained in Synthesis Example 23 was dissolved in toluene to a concentration of 20% by mass to prepare a surface treatment agent.

[0241] Example 15 The compound obtained in Synthesis Example 25 was dissolved in toluene to a concentration of 10% by mass to prepare a surface treatment agent.

[0242] Example 16 The compound obtained in Synthesis Example 26 was dissolved in isooctane to a concentration of 15% by mass to prepare a surface treatment agent.

[0243] Example 17 The compound obtained in Synthesis Example 28 was dissolved in toluene to a concentration of 20% by mass to prepare a surface treatment agent.

[0244] Example 18 The compound obtained in Synthesis Example 29 was dissolved in ethylcyclohexane to a concentration of 10% by mass to prepare a surface treatment agent.

[0245] Example 19 The compound obtained in Synthesis Example 30 was dissolved in toluene to a concentration of 30% by mass to prepare a surface treatment agent.

[0246] Example 20 The compound obtained in Synthesis Example 32 was dissolved in toluene to a concentration of 20% by mass to prepare a surface treatment agent.

[0247] Example 21 The compound obtained in Synthesis Example 33 was dissolved in propylene glycol monomethyl ether acetate to a concentration of 20% by mass to prepare a surface treatment agent.

[0248] Example 22 The compound obtained in Synthesis Example 34 was dissolved in toluene to a concentration of 20% by mass to prepare a surface treatment agent.

[0249] Example 23 The compound obtained in Synthesis Example 35 was dissolved in toluene to a concentration of 5% by mass to prepare a surface treatment agent.

[0250] Example 24 The compound obtained in Synthesis Example 2 was used as a surface treatment agent without dilution.

[0251] [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 %.

[0252] [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 %.

[0253] Comparative Example 3 No surface treatment agent.

[0254] Preparation of Surface Treatment Agents and Formation of Cured Coatings Surface treatment agents were prepared as in the above Examples and Comparative Examples. Each surface treatment agent was vacuum-deposited (vacuum deposition apparatus: ULVAC Kiko Co., Ltd., product number: VTR-350M, processing conditions: pressure 2.0 × 10) onto glass (Corning Gorilla (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: -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 a cured film with a thickness of 3 to 5 nm. [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

[0255] The glass on which the cured coating was formed was evaluated for water repellency, slipperiness, dirt wiping ability, and abrasion resistance (steel wool abrasion resistance and wet abrasion resistance) by the methods described below. Note that the same evaluation was carried out for Comparative Example 3, which was a glass (Gorilla manufactured by Corning Incorporated) that had not been subjected to any surface treatment and had been coated with SiO2 to a thickness of 10 nm on its outermost surface.

[0256] Evaluation of Water Repellency For the glass having the cured coating formed thereon, 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. The droplet image was then analyzed using FAMAS, the contact angle analysis software provided with 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: [Analysis Conditions] Method: Sessile 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 The results (initial water contact angle) are shown in Table 1. Initially, the Example and Comparative Examples 1 and 2 exhibited good water repellency (water contact angle of 90° or more).

[0257] 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 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)

[0258] 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 Corporation), the ink was allowed to dry, and the ink was then wiped off with tissue paper. The number of times the ink had to be 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

[0259] Evaluation of Steel Wool Abrasion Resistance The glass having the cured coating formed thereon was rubbed 3,000 times with steel wool using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions, and the contact angle of the cured coating with water (water repellency) was measured in the same manner as above to evaluate abrasion resistance. The test environmental conditions were 25°C and a relative humidity of 40%. The results (water contact angle after abrasion) are shown in Table 1. [Steel wool abrasion resistance test conditions] Steel wool: Bonstar #0000 Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2 Number of wear cycles: 3,000

[0260] Evaluation of Wet Abrasion Resistance: The glass having the cured coating formed thereon was rubbed 1,000 times with a cloth wetted with artificial sweat (pH 4.3) to the extent that the artificial sweat dripped onto the surface, without drying, using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions. The contact angle of the cured coating with water (water repellency) was then measured in the same manner as above, and the abrasion resistance was evaluated. The test environmental conditions were 25°C and a relative humidity of 40%. The results (water contact angle after abrasion) are shown in Table 1. [Wet abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2 Number of wear times: 1,000

[0261] The cured coatings of the surface treatment agents of Examples 1 to 24 had a predetermined number of consecutive carbon atoms in the molecular chain of the compound used (having a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms), which improved the intermolecular force between the linear unsubstituted aliphatic saturated hydrocarbon groups (alkyl chains) between adjacent compounds, resulting in good water repellency, slipperiness, dirt wiping ability, and abrasion resistance. The cured coating of the surface treatment agent of Comparative Example 1 had a small number of consecutive hydrocarbons in the compound used (having no monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms), which resulted in good water repellency but poor dirt wiping ability and abrasion resistance. The cured coating of the surface treatment agent of Comparative Example 2 had high water repellency due to the compound used having a fluorohydrocarbon chain, but poor abrasion resistance. Comparative Example 3 was a glass substrate that did not use a surface treatment agent, but since it was not surface treated, none of these characteristics were observed, and the effects of the Examples could be confirmed. As described above, with the surface treatment agents of the Examples, a cured coating film was obtained by vapor deposition coating that exhibited high levels of water repellency, slipperiness, ease of wiping off dirt, and abrasion resistance.

[0262]

[0263] Example 25 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.

[0264] Example 26 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.

[0265] Example 27 The compound obtained in Synthesis Example 3 was dissolved in isononane to a concentration of 0.2% by mass to prepare a surface treatment agent.

[0266] Example 28 The compound obtained in Synthesis Example 7 was dissolved in hexane / isooctane (30 / 70) to a concentration of 0.2% by mass to prepare a surface treatment agent.

[0267] Example 29 The compound obtained in Synthesis Example 9 was dissolved in ethylcyclohexane to a concentration of 0.15% by mass to prepare a surface treatment agent.

[0268] Example 30 The compound obtained in Synthesis Example 11 was dissolved in butyl acetate to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0269] Example 31 The compound obtained in Synthesis Example 13 was dissolved in propylene glycol monomethyl ether to a concentration of 0.2% by mass to prepare a surface treatment agent.

[0270] Example 32 The compound obtained in Synthesis Example 17 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0271] Example 33 The compound obtained in Synthesis Example 21 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0272] Example 34 The compound obtained in Synthesis Example 25 was dissolved in ethylcyclohexane to a concentration of 0.08% by mass to prepare a surface treatment agent.

[0273] Example 35 The compound obtained in Synthesis Example 27 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0274] Example 36 The compound obtained in Synthesis Example 30 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0275] Example 37 The compound obtained in Synthesis Example 32 was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0276] Comparative Example 4 The compound represented by the above formula (A') was dissolved in toluene to a concentration of 0.1% by mass to prepare a surface treatment agent.

[0277] Comparative Example 5 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.

[0278] [Comparative Example 6] No surface treatment agent.

[0279] Preparation of Surface Treatment Agents and Formation of Cured Coatings Surface treatment agents were prepared as in the above Examples and Comparative Examples. Each surface treatment agent was spray coated onto glass (Corning Gorilla (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 a cured coating with a film thickness of 3 to 5 nm. [Spray Coating Conditions] Atmosphere: 25°C / 50% relative humidity Nozzle distance: 50 mm Air pressure: 150 kPa Speed: 300 mm / min Pitch: 5 mm

[0280] The glass on which the cured coating was formed was evaluated for water repellency, slipperiness, dirt wiping ability, and abrasion resistance (steel wool abrasion resistance and wet abrasion resistance) by the methods described below. Note that the same evaluation was carried out for Comparative Example 6, which was a glass (Gorilla manufactured by Corning Incorporated) coated with SiO2 to a thickness of 10 nm on the outermost surface without any surface treatment.

[0281] Evaluation of Water Repellency For the glass having the cured coating formed thereon, 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 using a CCD camera connected to the contact angle meter. The droplet image was then analyzed using FAMAS, a contact angle analysis software provided with 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: [Analysis Conditions] Method: Sessile 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 The results (initial water contact angle) are shown in Table 2. Initially, Example and Comparative Examples 4 and 5 exhibited good water repellency.

[0282] Evaluation of Slipperiness The coefficient of dynamic friction of the glass having the cured coating formed thereon produced 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 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)

[0283] Evaluation of Dirt Wiping Ability A 2 cm straight line was drawn on the glass surface on which the cured coating film prepared above was formed using a Hi-Mackey (manufactured by Zebra Corporation), the ink was allowed to dry, and the ink was then wiped off with tissue paper. The number of times the ink had to be 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

[0284] Evaluation of Steel Wool Abrasion Resistance The glass having the cured coating formed thereon was rubbed 3,000 times with steel wool using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions, and the contact angle of the cured coating with water (water repellency) was measured in the same manner as above to evaluate abrasion resistance. The test environmental conditions were 25°C and a relative humidity of 40%. The results (water contact angle after abrasion) are shown in Table 2. [Steel wool abrasion resistance test conditions] Steel wool: Bonstar #0000 Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2 Number of wear cycles: 3,000

[0285] Evaluation of Wet Abrasion Resistance: The glass having the cured coating formed thereon was rubbed 1,000 times with a cloth wetted with artificial sweat (pH 4.3) to the extent that the artificial sweat dripped onto the surface without drying, using a rubbing tester (manufactured by Shinto Scientific Co., Ltd.) under the following conditions. The contact angle of the cured coating with water (water repellency) was then measured in the same manner as above, and the abrasion resistance was evaluated. The test environmental conditions were 25°C and a relative humidity of 40%. The results (water contact angle after abrasion) are shown in Table 2. [Wet abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2 Number of wear times: 1,000

[0286] The cured coatings of the surface treatment agents of Examples 25 to 37 had a predetermined number of consecutive carbon atoms in the molecular chain of the compound used (having a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms), which improved the intermolecular force between the linear unsubstituted aliphatic saturated hydrocarbon groups (alkyl chains) between adjacent compounds, resulting in good water repellency, slipperiness, dirt wiping ability, and abrasion resistance. The cured coating of the surface treatment agent of Comparative Example 4 had a small number of consecutive hydrocarbons in the compound used (having no monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms), which resulted in good water repellency but poor dirt wiping ability and abrasion resistance. The cured coating of the surface treatment agent of Comparative Example 5 had high water repellency due to the compound used having a fluorohydrocarbon chain, but poor abrasion resistance. Comparative Example 6 was a glass substrate without a surface treatment agent, but since it was not surface treated, none of these characteristics were observed, and the effects of the Examples could be confirmed. As described above, with the surface treatment agents of the Examples, even by spray coating, which is an example of wet coating, it was possible to obtain a cured coating that exhibited high levels of water repellency, slipperiness, dirt wipeability, and abrasion resistance.

[0287]

Claims

1. The following general formula (1) (In the formula, R 1 is a monovalent hydrocarbon group having 12 to 80 carbon atoms and containing no branched hydrocarbon structure, and which may contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon atoms, and which contains a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms; R 2 are independently a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a —OSi(CH3)3 group, a —OSi(C2H5)3 group, an amino group, a thiol group, a monovalent hydrocarbon group having 1 or 2 carbon atoms, R 1 , -VZ-(Y-A) m or -Y-A, wherein U is a single bond, a carbon atom, or a trivalent or tetravalent organic group, V is a single bond or a divalent hydrocarbon group which may contain at least one atom selected from oxygen atoms, nitrogen atoms, and sulfur atoms, Z is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a tri- to octavalent organic group, Y is independently a single bond or a divalent hydrocarbon group which may contain at least one atom selected from oxygen atoms, nitrogen atoms, sulfur atoms, and silicon atoms, A is independently a monovalent reactive group, k is 0, 1, or 2, and m is an integer from 1 to 7.

2. A in the above formula (1) is represented by the following general formula (2): (wherein R is independently an alkyl group or a phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer of 1 to 3), or the following general formula (3):

2. The hydrocarbon terminal group-containing compound according to claim 1, wherein n'' is a group represented by the formula: (wherein n'' is a number from 0 to 3, and n' is (3-n'') / 2).

3. In the above formula (1), R 1 is expressed by the following formula (4): (In the formula, R A is a monovalent hydrocarbon group having 3 to 80 carbon atoms, which is linear, cyclic, or a combination thereof; Q is independently a divalent group selected from the group consisting of an oxygen atom, a sulfur atom, a diorganosilylene group, a silalkylene structure or a silarylene structure, a linear divalent organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic divalent 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, and a divalent nitrogen-containing heterocyclic group; R B are independently a single bond, or a divalent hydrocarbon group having 1 to 70 carbon atoms which is linear, cyclic, or a combination thereof, and p is an integer of 0 to 10. A , R B is a monovalent or divalent linear unsubstituted aliphatic saturated hydrocarbon group having 12 or more carbon atoms, and p is an integer of 2 to 10, then R B is not a single bond, and the total number of carbon atoms in the formula (4) is 12 to 80.

4. The hydrocarbon terminal group-containing compound according to claim 1, wherein in the above formula (1), Y is a single bond or a group 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 12 carbon atoms which includes an arylene group having 6 to 8 carbon atoms; a divalent group in which alkylene groups having 1 to 8 carbon atoms are mutually bonded 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 12 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.

5. In the above formula (1), Z is a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur 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 the hydrocarbon terminal group-containing compound according to claim 1, which is a trivalent group represented by the formula (I) (wherein ≡I 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.

6. The hydrocarbon terminal group-containing compound according to claim 1, wherein in the above formula (1), U is a single bond, or a trivalent or tetravalent group selected from the group consisting of carbon atoms and trivalent or tetravalent cyclic hydrocarbon groups having 5 to 8 carbon atoms.

7. In the above formula (1), R 2 is a hydrogen atom, a halogen atom, a hydroxyl group, a siloxy group, a —OSi(CH) group, a —OSi(CH) group, an amino group, a thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms.

8. The hydrocarbon terminal group-containing compound according to claim 2, wherein in the above formula (2), X is selected from the group consisting of a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, an alkoxyalkoxy group having 2 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, a halogen group, and a dialkylamino group having 2 to 10 carbon atoms.

9. A surface treatment agent comprising the hydrocarbon terminal group-containing compound according to claim 1.

10. A cured coating formed using the surface treatment agent according to claim 9.

11. An article having the cured coating of claim 10.

12. The article according to claim 11, characterized in that the water contact angle after steel wool abrasion is 75° or more, as described under the following conditions: [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 Number of wear cycles: 3,000 13. The article according to claim 11, characterized in that the water contact angle after wet abrasion is 75° or more, as described under the following conditions: [Wet abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1 cm 2 Travel distance (one way): 40 mm Travel speed: 4,800 mm / min Load: 500 gf / 1 cm 2 Number of wear times: 1,000 14. The article according to claim 11, characterized in that the coefficient of dynamic friction is 0.20 or less.

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