Surface treatment agent, article, and method for forming a coating.

Abstract

The present invention provides a non-fluorine-based (i.e., one that does not contain fluorine atoms in its molecule) surface treatment agent that can form a cured film with excellent water repellency, slipperiness, dirt-wiping properties, and abrasion resistance on various substrates, particularly substrates whose surface is at least made of resin; an article surface-treated with the surface treatment agent; and a method for forming a film by coating a substrate with the surface treatment agent. [Solution] (A) A nonfluorine-based hydrocarbon end group-containing compound and / or a partially reacted condensate thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, (B) Compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or hydrolyzable silyl group at both ends of the molecular chain: 1 to 50% by mass of the total of components (A) and (B) A non-fluorine-based surface treatment agent containing [specific component].

Description

[Technical Field]

[0001] The present invention relates to a surface treatment agent containing a hydrocarbon terminal group compound, and more particularly to a surface treatment agent that forms a film with excellent water repellency, slipperiness, dirt-wiping properties, abrasion resistance, and adhesion to various substrates, especially substrates whose surface is at least made of resin; an article surface-treated with the surface treatment agent; and a method for forming a film by coating a substrate with the surface treatment agent. [Background technology]

[0002] In recent years, the use of touch panels in displays such as smartphones and in-car displays has accelerated. However, because touch panels have exposed screens, they are frequently in direct contact with fingers and cheeks, making them prone to dirt and sebum buildup. Therefore, there is a growing demand for technologies that make the display surface less prone to fingerprints and easier to clean, in order to improve appearance and visibility. The development of materials that can meet these demands is highly desirable. In particular, since the surface of touch panel displays is prone to fingerprint smudges, there is a desire to provide a water- and oil-repellent layer. However, while conventional water- and oil-repellent layers have high water and oil repellency and are excellent at wiping away dirt, they lack sufficient abrasion resistance and have the problem of fingerprints being very noticeable when they do adhere to the surface.

[0003] Generally, fluoropolyether group-containing compounds have very low surface free energy, resulting in properties such as water and oil repellency, chemical resistance, lubricity, mold release, and antifouling. These properties are utilized industrially in a wide range of applications, including water, oil, and antifouling agents for paper and textiles, lubricants for magnetic recording media, oil inhibitors and mold release agents for precision equipment, cosmetics, and protective films. However, these properties also mean non-stickiness and poor adhesion to other substrates; while they can be applied to substrate surfaces, achieving a strong bond between the film and the substrate is difficult.

[0004] Silane coupling agents are well-known for bonding organic compounds to substrate surfaces such as glass and cloth, and are widely used as coating agents for various substrate surfaces. A silane coupling agent has 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 with moisture in the air to form a film. This film becomes a strong and durable coating because the hydrolyzable silyl group chemically and physically bonds with the surface of glass, metal, etc.

[0005] Therefore, compositions have been disclosed that use a fluoropolyether group-containing polymer obtained by introducing a hydrolyzable silyl group into a fluoropolyether group-containing compound, which can easily adhere to the substrate surface and form a coating on the substrate surface that has water-repellent and oil-repellent properties, chemical resistance, lubricity, mold release properties, and antifouling properties (Patent Documents 1-6: JP 2008-534696, JP 2008-537557, JP 2012-072272, JP 2012-157856, JP 2013-136833, JP 2015-199906).

[0006] However, fluorine-containing compounds, such as those containing fluoropolyether groups, are difficult to decompose in nature and tend to accumulate in the environment. Therefore, there is a growing need for the development of surface protective agents for non-fluorine-based materials.

[0007] In developing surface protectants for non-fluorinated materials, water repellency, slipperiness, dirt-wiping properties, and abrasion resistance are required, as well as adhesion to the substrate, particularly to substrates with a resin surface. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] Special Publication No. 2008-534696 [Patent Document 2] Special Publication No. 2008-537557 [Patent Document 3] Japanese Patent Publication No. 2012-072272 [Patent Document 4] Japanese Patent Publication No. 2012-157856 [Patent Document 5] Japanese Patent Publication No. 2013-136833 [Patent Document 6] Japanese Patent Publication No. 2015-199906 [Overview of the project] [Problems that the invention aims to solve]

[0009] The present invention has been made in view of the above circumstances, and aims to provide a non-fluorine-based (i.e., one that does not contain fluorine atoms in its molecule) surface treatment agent that can form a cured film with excellent water repellency, slipperiness, dirt-wiping properties, and abrasion resistance on various substrates, particularly substrates whose surface is at least made of resin, as well as an article surface-treated with the surface treatment agent, and a method for forming a film by coating a substrate with the surface treatment agent. [Means for solving the problem]

[0010] As a result of diligent research to solve the above objectives, the present inventors have found that a nonfluorine-based hydrocarbon end group-containing compound and / or a partially reacted condensate thereof, comprising (A) a linear, branched, or cyclic monovalent hydrocarbon group having at least one carbon 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, and (B) a compound having a functional group and a silanol group or a hydrolyzable silyl group at the end of the molecular chain, or a compound having a silanol group or a hydrolyzable silyl group at both ends of the molecular chain: a nonfluorine-based surface treatment agent comprising 1 to 50% by mass of the total of components (A) and (B), can form a cured film on various substrates, particularly substrates whose surface is at least made of resin, that exhibits excellent water repellency, slipperiness, dirt-wiping properties, abrasion resistance, and especially fabric abrasion resistance, leading to the present invention.

[0011] Accordingly, the present invention provides a surface treatment agent and article, as well as a method for forming a coating. [1] (A) Nonfluorinated hydrocarbon end group-containing compounds and / or partially reaction condensates thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, (B) Compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or hydrolyzable silyl group at both ends of the molecular chain: 1 to 50% by mass of the total of components (A) and (B) A non-fluorine-based surface treatment agent containing [specific component]. [2] The surface treatment agent according to [1], wherein the monovalent hydrocarbon group in the hydrocarbon terminal group-containing compound of component (A) is selected from alkyl groups having 6 to 32 carbon atoms and aryl groups having 6 to 32 carbon atoms. [3] The surface treatment agent according to [1] or [2], wherein the hydrocarbon terminal group-containing compound of component (A) has two or more monovalent hydrocarbon groups and has a trivalent or higher linking group that bonds the two or more monovalent hydrocarbon groups to at least one reactive silyl group. [4] The hydrocarbon terminal group-containing compound of component (A) is of the following general formula (1) [ka] [In the formula, R 1 R may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 4 to 32 carbon atoms, 2A is a hydrogen atom, halogen atom, hydroxyl group, siloxy group, amino group, thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U is a carbon atom, silicon atom, nitrogen atom, or a trivalent or tetravalent organic group; V is independently a single bond or a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, and sulfur atoms; Z is independently a single bond, carbon atom, silicon atom, nitrogen atom, sulfur atom, or a 3-8 valent organic group; Y is independently a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, sulfur, and silicon atoms; and A is independently the following general formula (2) [ka] (In the formula, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) Or the following general formula (3) [ka] (In the formula, n'' is a number between 0 and 3, and n'' is (3-n'') / 2.) The base is represented by , where k1 is an integer between 1 and 3, k2 is 0 or 1, k3 is an integer between 1 and 3, k1 + k2 + k3 is 3 or 4, and m is an integer between 1 and 7. A surface treatment agent according to any one of [1] to [3], which is a hydrocarbon terminal group-containing compound represented by [1]. [5] The surface treatment agent according to [4], wherein k1 is 2 or 3 in the above formula (1). [6] In the above equation (1), R 1 However, the following formula [ka] (In the formula, R AQ is independently a monovalent hydrocarbon group having 4 to 32 carbon atoms, which may be linear, branched, cyclic, or a combination thereof, and Q is independently an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a sylalkylene structure or sylarylene structure, and a linear or branched or cyclic divalent organopolysiloxane residue having 2 to 10 silicon atoms, or having 3 to 10 silicon atoms, a carbonyl (ketone) group, an ester group, a carbonate group, a sulfinyl group, a sulfonyl group, a thioester group, a thiocarbonate group, a thiocarbamate group, an amino group, an amide group, or a carbamate Q' is a divalent group selected from the group consisting of a group, a urea group, and a divalent nitrogen-containing heterocyclic group, Q' is independently a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear or branched or cyclic trivalent organopolysiloxane residue having 2 to 10 silicon atoms, a trivalent amide group, and a trivalent nitrogen-containing heterocyclic group, Q'' is independently a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, and a linear or branched or cyclic tetravalent organopolysiloxane residue having 2 to 10 silicon atoms, R B R is a divalent hydrocarbon group having 1 to 29 carbon atoms, which may be independently single-bonded, linear, branched, or cyclic, and C R is independent A (or a hydrogen atom, where p is an integer between 0 and 10. However, the total number of carbon atoms in each structure is 32 or less.) A surface treatment agent according to [4] or [5], which is any group represented by [4]. [7] In the above equation (1), R 1 The surface treatment agent according to any one of [4] to [6], wherein the carbon atom may independently contain at least one selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 11 to 32 carbon atoms. [8] In the above formula (1), Y is a group selected from the group consisting of an alkylene group having 1 to 20 carbon atoms which may contain at least one selected from an oxygen atom, a nitrogen atom and a sulfur atom, an alkylene group having 1 to 10 carbon atoms containing 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 silaalkylene structure, a silaarylene structure or a nitrogen-containing heterocyclic group, and a divalent group in which an alkylene group having 1 to 10 carbon atoms is bonded to a bond of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms, which is the surface treatment agent according to any one of [4] to [7]. 〔9〕 In the above formula (1), Z is a single bond, or a trivalent group represented by 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, -SiR 3 =(R 3 is a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), a trivalent group represented by -CR 4 =(R 4 is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms), a trivalent group selected from the group consisting of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent to octavalent 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-containing group, which is the surface treatment agent according to any one of [4] to [8]. 〔10〕 In the above formula (1), U is a trivalent or tetravalent group selected from the group consisting of a carbon atom, a silicon atom, a nitrogen atom, a trivalent or tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic trivalent or tetravalent organopolysiloxane residue having 3 to 10 silicon atoms, a trivalent amide group, a trivalent carbamate group, a trivalent or tetravalent urea group, and a trivalent or tetravalent nitrogen-containing heterocyclic group-containing group, which is the surface treatment agent according to any one of [4] to [9]. 〔11〕 A surface treatment agent according to any one of [1] to

[10] , wherein the functional group of the compound having a functional group and a silanol group or a hydrolyzable silyl group at the molecular chain terminus of component (B) is an amino group, an epoxy group, a thiol group, an acryloyl group, or a methacryloyl group.

[12] A compound having a functional group and a silanol group or a hydrolyzable silyl group at the end of the molecular chain of component (B), or a compound having a silanol group or a hydrolyzable silyl group at both ends of the molecular chain, is given by the following general formula (4) [ka] [In the formula, B is the same as in the following formulas (5a) to (5f)] [ka] (In the formula, R′ is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R'' is independently an alkyl group having 1 to 3 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) The group is one of the groups represented by (5f), where D is independently an alkylene group having 1 to 10 carbon atoms, E is independently -O-, -NH-, or -S-, R is independently an alkyl group or phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, g is an integer from 0 to 3 (however, if B is a group represented by formula (5f), g is an integer from 1 to 3), and n is an integer from 1 to 3. A silane compound represented by [1] to

[11] , which is a surface treatment agent according to any one of the following:

[13] An article whose surface has been treated with any of the surface treatment agents described in [1] to

[12] .

[14] The article described in

[13] , wherein at least one surface of the article is made of resin.

[15] A method for forming a film by applying a surface treatment agent to a substrate, wherein the surface treatment agent is (A) Nonfluorinated hydrocarbon end group-containing compounds and / or partially reaction condensates thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, (B) Compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or hydrolyzable silyl group at both ends of the molecular chain: 1 to 50% by mass of the total of components (A) and (B) A method for forming a coating using a non-fluorine-based surface treatment agent.

[16] The method for forming a film according to

[15] , wherein the monovalent hydrocarbon group in the hydrocarbon terminal group-containing compound of component (A) is selected from alkyl groups having 6 to 32 carbon atoms and aryl groups having 6 to 32 carbon atoms.

[17] The method for forming a film according to

[15] or

[16] , wherein the hydrocarbon terminal group-containing compound of component (A) has two or more monovalent hydrocarbon groups and has a trivalent or higher linking group that bonds the two or more monovalent hydrocarbon groups to at least one reactive silyl group.

[18] The hydrocarbon terminal group-containing compound of component (A) is of the following general formula (1) [ka] [In the formula, R 1 R may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 4 to 32 carbon atoms, 2A is a hydrogen atom, halogen atom, hydroxyl group, siloxy group, amino group, thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U is a carbon atom, silicon atom, nitrogen atom, or a trivalent or tetravalent organic group; V is independently a single bond or a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, and sulfur atoms; Z is independently a single bond, carbon atom, silicon atom, nitrogen atom, sulfur atom, or a 3-8 valent organic group; Y is independently a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, sulfur, and silicon atoms; and A is independently the following general formula (2) [ka] (In the formula, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) Or the following general formula (3) [ka] (In the formula, n'' is a number between 0 and 3, and n'' is (3-n'') / 2.) The base is represented by , where k1 is an integer between 1 and 3, k2 is 0 or 1, k3 is an integer between 1 and 3, k1 + k2 + k3 is 3 or 4, and m is an integer between 1 and 7. A method for forming a coating according to any one of

[15] to

[17] , which is a hydrocarbon terminal group-containing compound represented by . [Effects of the Invention]

[0012] The surface treatment agent of the present invention, while being non-fluorine-based, can form a cured film with excellent water repellency, slipperiness, dirt-wiping properties, and abrasion resistance on various substrates, particularly substrates whose surface is at least made of resin. Articles surface-treated with this surface treatment agent exhibit excellent water repellency, slipperiness, dirt-wiping properties, and abrasion resistance. [Modes for carrying out the invention]

[0013] The surface treatment agent of the present invention is (A) Nonfluorinated hydrocarbon end group-containing compounds and / or partially reaction condensates thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, (B) Compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or hydrolyzable silyl group at both ends of the molecular chain: 1 to 50% by mass of the total of components (A) and (B) It is a non-fluorine-based surface treatment agent containing [specific ingredient].

[0014] Component (A) of the present invention is a hydrocarbon-end group-containing compound and / or a partially reacted condensate thereof. The hydrocarbon-end group-containing compound has at least one monovalent hydrocarbon group with a predetermined number of carbon atoms at the end of its molecular chain, thereby improving molecular mobility. As a result, the cured film of the surface treatment agent containing the hydrocarbon-end group-containing compound exhibits water repellency, as well as excellent slipperiness, dirt-wiping properties, and abrasion resistance. Furthermore, component (B) is a compound having a functional group and a silanol group or hydrolyzable silyl group at the end of its molecular chain, or a compound having a silanol group or hydrolyzable silyl group at both ends of its molecular chain. The functional group or silanol group or hydrolyzable silyl group contained in it adheres to various substrates, especially substrates whose surface is at least made of resin, and the silanol group or hydrolyzable silyl group reacts with component (A) to act as a primer between component (A) and various substrates. As a result, adhesion to various substrates is improved, and the strong adhesion improves abrasion resistance.

[0015] [Ingredients (A)] Component (A) is a nonfluorinated hydrocarbon end-group-containing compound and / or a partially reacted condensate thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain.

[0016] In hydrocarbon-terminal group-containing compounds, the monovalent hydrocarbon group is a linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms, preferably a group selected from alkyl groups having 6 to 32 carbon atoms and aryl groups having 6 to 32 carbon atoms, and more preferably an alkyl group having 11 to 32 carbon atoms. Furthermore, in hydrocarbon-terminal group-containing compounds, it is preferable to have two or more monovalent hydrocarbon groups with a predetermined number of carbon atoms, and more preferable to have two or three. Furthermore, the hydrocarbon-terminal group-containing compound preferably has a linking group that connects at least one monovalent hydrocarbon group with at least one reactive silyl group, and the linking group is preferably trivalent or higher, and more preferably trivalent or tetravalent.

[0017] The hydrocarbon terminal group-containing compound is preferably a hydrocarbon terminal group-containing compound represented by the following general formula (1). [ka] [In the formula, R 1 R may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 4 to 32 carbon atoms, 2 A is a hydrogen atom, halogen atom, hydroxyl group, siloxy group, amino group, thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U is a carbon atom, silicon atom, nitrogen atom, or a trivalent or tetravalent organic group; V is independently a single bond or a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, and sulfur atoms; Z is independently a single bond, carbon atom, silicon atom, nitrogen atom, sulfur atom, or a 3-8 valent organic group; Y is independently a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, sulfur, and silicon atoms; and A is independently the following general formula (2) [ka] (In the formula, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) Or the following general formula (3) [ka] (In the formula, n'' is a number between 0 and 3, and n'' is (3-n'') / 2.) The base is represented by , where k1 is an integer between 1 and 3, k2 is 0 or 1, k3 is an integer between 1 and 3, k1 + k2 + k3 is 3 or 4, and m is an integer between 1 and 7.

[0018] In the above equation (1), R 1 This may independently contain at least one atom selected from oxygen, sulfur, nitrogen, and silicon, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 4 to 32 carbon atoms, preferably 6 to 32 carbon atoms, more preferably 11 to 32 carbon atoms. Here, if at least one atom selected from oxygen, sulfur, nitrogen, and silicon is included, then the group may be an ether group (-O-), a carbonyl (ketone) group (-C(=O)-), an ester group (-C(=O)O-), a carbonate group (-OC(=O)O-), a thioether group (-S-), a sulfinyl group (-S(=O)-), a sulfonyl group (-S(=O)2-), a thioester group (-C(=O)-S-), a thiocarbonate group (-SC(=S)S-), or a thiocarbamate group (-OC(=S)NR). 5 -, -SC(=O)NR 5 -(R 5 (These are hydrogen atoms, C1-C3 alkyl groups or phenyl groups, the same applies below), amino groups (-NR) 5 -), amide group (-C(=O)NR 5 -), carbamate group (-OC(=O)NR 5 -), urea group (-NR 5 C(=O)NR 5-) Preferably contains divalent groups such as oxazole groups, imidazole groups, triazole groups, cyanurate groups, isocyanurate groups, diorganosilylene groups, organopolysiloxane residues, sylalkylene groups, and sylarylene groups.

[0019] R 1 The base represented by the following formula is preferred. [ka] (In the formula, R A Q is independently a monovalent hydrocarbon group having 4 to 32 carbon atoms, which may be linear, branched, cyclic, or a combination thereof, and Q is independently an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a sylalkylene structure or sylarylene structure, and a linear or branched or cyclic divalent organopolysiloxane residue having 2 to 10 silicon atoms, or 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, or a divalent nitrogen-containing heterocyclic group (divalent oxazole group, divalent imidazo). Q' is a divalent group selected from the group consisting of a 4-valent group, a divalent triazole group, etc., and Q' is a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear or branched or cyclic trivalent organopolysiloxane residue having 2 to 10 silicon atoms, a trivalent amide group, a trivalent nitrogen-containing heterocyclic group (trivalent cyanurate group, trivalent isocyanurate group, trivalent triazole group, etc.), and Q'' is a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear or branched or cyclic tetravalent organopolysiloxane residue having 2 to 10 silicon atoms, etc., R B R is a divalent hydrocarbon group having 1 to 29 carbon atoms, which may be independently single-bonded, linear, branched, or cyclic, and C R is independent A(or a hydrogen atom, where p is an integer between 0 and 10. However, the total number of carbon atoms in each structure is 32 or less.)

[0020] In the above formula, R A R is a monovalent hydrocarbon group having 4 to 32 carbon atoms, preferably 6 to 32 carbon atoms, more preferably 11 to 32 carbon atoms, which may be linear, branched, cyclic, or a combination thereof. A For example, the following can be cited: [ka] [ka] (In the formula, x is an integer between 2 and 31, preferably between 5 and 31, more preferably between 10 and 31, and y and y' are integers of 1 or more such that the sum of the number of carbon atoms in each structure is 32 or less.)

[0021] In the above formula, Q is independently an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a sylalkylene structure or sylarylene structure, and a divalent organopolysiloxane residue having 2 to 10 silicon atoms, particularly a linear structure with 2 to 8 silicon atoms, or a branched or cyclic structure with 3 to 10 silicon atoms, particularly a 3 to 8 silicon atom, a carbonyl (ketone) group (-C(=O)-), an ester group (-C(=O)O-), a carbonate group (-OC(=O)O-), a sulfinyl group (-S(=O)-), a sulfonyl group (-S(=O)2-), a thioester group (-C(=O)-S-), a thiocarbonate group (-SC(=S)S-), or a thiocarbamate group (-OC(=S)NR 5 -, -SC(=O)NR 5 -(R 5 (The above is the same), amino group (-NR 5 -), amide group (-C(=O)NR 5 -), carbamate group (-OC(=O)NR 5 -), urea group (-NR 5 C(=O)NR 5-) A divalent group selected from the group consisting of divalent nitrogen-containing heterocyclic groups (such as divalent oxazole groups, divalent imidazole groups, and divalent triazole groups).

[0022] Here, the groups that bond to silicon atoms in diorganosilylene groups, sylalkylene structures, sylarylene structures, and organopolysiloxane residues are preferably alkyl groups such as methyl, ethyl, propyl, and butyl groups, or phenyl groups, having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms. Furthermore, the alkylene groups in the sylalkylene structures are preferably ethylene groups, propylene groups (trimethylene group, methylethylene group), butylene groups (tetramethylene group, methylpropylene group), etc., having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. In addition, the organopolysiloxane residue may contain a sylalkylene structure in which two silicon atoms are bonded by alkylene groups such as ethylene and propylene groups.

[0023] Examples of such Q include those shown below. Note that in the structure below, the left-hand bond is R A or R B It joins with R B It combines with it. [ka] [ka] [ka] [ka] (In the formula, f is an integer between 2 and 4, and e is an integer between 1 and 9.)

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

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

[0026] Examples of such Q' include those shown below. In the structure below, the left-hand bond is R A or R B And the bond on the right is R B And the other bonds are R C It combines with it. [ka] [ka] (In the formula, f is an integer between 2 and 4.)

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

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

[0029] Examples of such Q'' include those shown below. In the structure below, the left-hand bond is R A or R B And the bond on the right is R B And the other bonds are R C It combines with it. [ka] [ka]

[0030] In the above formula, R B These are divalent hydrocarbon groups having 1 to 29 carbon atoms, which may be independently single-bonded, linear, branched, or cyclic, and the following are examples: [ka] (In the formula, z is an integer between 1 and 10.)

[0031] In the above formula, R C R is independent A Or it is a hydrogen atom. Note that R C R A If so, then R A It may be the same as or different from it.

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

[0033] Such R 1The following are preferred for use. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] (In the formula, x, y, y', and z are the same as above, except that the total number of carbon atoms in each structure is between 3 and 32.)

[0034] In the above equation (1), R 2 These are hydrogen atoms, halogen atoms, hydroxyl groups, siloxy groups, amino groups, thiol groups, or monovalent hydrocarbon groups having 1 or 2 carbon atoms (methyl group, ethyl group). R 2 Preferably, the atoms are hydrogen atoms, chlorine atoms, hydroxyl groups, methyl groups, and ethyl groups.

[0035] In formula (1) above, U is a carbon atom, a silicon atom, a nitrogen atom, or a trivalent or tetravalent organic group. Examples of trivalent or tetravalent organic groups include trivalent or tetravalent cyclic hydrocarbon groups having 6 to 8 carbon atoms, linear trivalent or tetravalent organopolysiloxane residues having 2 to 10 silicon atoms, particularly 2 to 8 silicon atoms, or branched or cyclic trivalent or tetravalent organopolysiloxane residues having 3 to 10 silicon atoms, particularly 3 to 8 silicon atoms, trivalent amide groups (-C(=O)N=), trivalent carbamate groups (-OC(=O)N=), and trivalent or tetravalent urea groups (-NR 5 C(=O)N= or =NC(=O)N=(R 5 It is preferable that the group is a trivalent or tetravalent group selected from the above (as described above) and trivalent or tetravalent nitrogen-containing heterocyclic groups (such as trivalent cyanurate groups, trivalent isocyanurate groups, and trivalent triazine ring-containing groups).

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

[0037] Examples of such U are shown below. In the structure below, it is preferable that the right-hand bond connects to V. [ka] [ka] [ka] [ka]

[0038] In formula (1) above, V may independently consist of a single bond or at least one selected from an oxygen atom, a nitrogen atom, and a sulfur atom. Preferably, V is a divalent hydrocarbon group having 1 to 20 carbon atoms and is a linking group connecting the U group and the Z group. When Z is a single bond, V is preferably a single bond. Examples of the divalent hydrocarbon group include a C1-C10 alkylene group which may contain at least one atom selected from oxygen, nitrogen, and sulfur, and a C1-C10 alkylene group which contains a C6-C8 arylene group (for example, a C7-C18 alkylene-arylene group).

[0039] Examples of such V include, in addition to single bonds, the following. In the structure below, the bond on the left is bonded to U, and the bond on the right is bonded to Z. [ka] [ka] [ka] [ka] (In the formula, q is an integer between 1 and 10, r, s, and t are each integers between 1 and 8, the sum of r and s is an integer between 2 and 10, and the sum of r, s, and t is an integer between 3 and 10.)

[0040] In formula (1) above, Z is independently a single bond, a carbon atom, a silicon atom, a nitrogen atom, a sulfur atom, or a 3- to 8-valent organic group. Examples of 3- to 8-valent organic groups include trivalent or tetravalent cyclic hydrocarbon groups with 6 to 8 carbon atoms, -SiR 3 =(R 3 (A trivalent group represented by a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), -CR 4 =(R 4(where is a hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms) trivalent groups, linear groups with 2 to 10 silicon atoms, especially 2 to 8 silicon atoms, or branched or cyclic tri- to octavalent organopolysiloxane residues with 3 to 10 silicon atoms, especially 3 to 8 silicon atoms, trivalent amide groups (-C(=O)N=), trivalent carbamate groups (-OC(=O)N=), trivalent or tetravalent urea groups (-NR 5 C(=O)N= or =NC(=O)N=(R 5 Examples include the same as above, and 3- to 8-valent nitrogen-containing heterocyclic groups (such as trivalent cyanurate groups, trivalent isocyanurate groups, and trivalent or tetravalent triazine ring-containing groups).

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

[0042] Examples of such Z bonds include, in addition to single bonds, those shown below. In the structure below, the bond on the left is bonded to V, and the other bonds are bonded to Y. [ka] [ka] [ka] [ka] (In the formula, f is an integer between 2 and 4.)

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

[0044] Here, the groups that bond to silicon atoms in diorganosilylene groups, sylalkylene structures, sylarylene structures, and organopolysiloxane residues are preferably alkyl groups such as methyl, ethyl, propyl, and butyl groups, or phenyl groups, having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms. Furthermore, the alkylene groups in the sylalkylene structures are preferably ethylene groups, propylene groups (trimethylene group, methylethylene group), butylene groups (tetramethylene group, methylpropylene group), etc., having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms. In addition, the organopolysiloxane residue may contain a sylalkylene structure in which two silicon atoms are bonded by alkylene groups such as ethylene and propylene groups.

[0045] Examples of such Y groups include the following. In the structure below, the left-hand bond is bonded to Z, and the right-hand bond is bonded to A. It is preferable that there are two or more repeating units represented by (CH2) that bond to A. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] (In the formula, a is an independent integer between 1 and 10, b, c, and d are each integers between 1 and 8, the sum of b and c is an integer between 2 and 10, and the sum of b, c, and d is an integer between 3 and 10. e is an integer between 1 and 9, and f is an integer between 2 and 4.)

[0046] In the above equation (1), A is independently given by the following general equation (2) [ka] (In the formula, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) Or the following general formula (3) [ka] (In the formula, n'' is a number between 0 and 3, and n'' is (3-n'') / 2.) It is a base represented by .

[0047] In formula (2) above, R is independently an alkyl group such as a methyl group, ethyl group, propyl group, or butyl group having 1 to 4 carbon atoms, or a phenyl group, with a methyl group being preferred among them. Furthermore, in formula (2) above, X is independently a hydroxyl group or a hydrolyzable group. Examples of such X include hydroxyl groups; C1-C10 alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, and butoxy groups; C2-C10 alkoxyalkoxy groups such as methoxymethoxy and methoxyethoxy groups; C1-C10 acyloxy groups such as acetoxy groups; C2-C10 alkenyloxy groups such as isopropenoxy and cyclopentenyloxy groups; halogen groups such as chlor, bromo, and iodine groups; and C2-C10 dialkylamino groups such as dimethylamino and diethylamino groups. Among these, methoxy, ethoxy, isopropenoxy, and chlor groups are preferred. X may be the same or different.

[0048] In formula (3) above, n'' is a number between 0 and 3 (a positive number less than or equal to 3), and it is preferable that n'' < 3, and more preferably that n'' = 0. Note that in formula (3) above, when n'' = 3, the general formula (1) above represents the molecular formula (structural formula) of the hydrocarbon terminal group-containing compound (monomer monomer), and in formula (3) above, when n'' < 3, the general formula (1) above represents the compositional formula of the hydrocarbon terminal group-containing compound (polysilazane compound). In equation (3) above, n' is (3-n'') / 2, and preferably 1.5.

[0049] In the above formula (1), k1 is an integer from 1 to 3, preferably 2 or 3, k2 is 0 or 1, k3 is an integer from 1 to 3, k1+k2+k3 is 3 or 4, when U is trivalent, k1+k2+k3 is 3, and when U is tetravalent, k1+k2+k3 is 4. Furthermore, m is an integer between 1 and 7, preferably between 1 and 3.

[0050] The following structures are examples of hydrocarbon terminal group-containing compounds represented by the above formula (1). 1 , R 2 By changing the combinations of U, V, Z, Y, A, k1, k2, k3, and m, several different hydrocarbon end-group-containing compounds can be obtained.

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[0060] Examples of the method for preparing the hydrocarbon terminal group-containing compound represented by the general formula (1) of the present invention include the following methods. [Preparation Method 1] A hydrocarbon terminal group-containing compound having an alkenyl group at its terminus can be mixed with a compound having an SiH group and a hydrolyzable silyl group, and a hydrosilylation addition reaction can be carried out in the presence of a hydrosilylation catalyst to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a hydrolyzable silyl group at its terminus).

[0061] Here, examples of hydrocarbon terminal group-containing compounds having an alkenyl group at the terminal include compounds represented by the following formula (1A). [ka] (In the formula, R 1 , R 2 U, V, Z, k1, k2, k3, k1+k2+k3, and m are the same as above. Y 1 (This may independently contain a single bond or at least one atom selected from oxygen, nitrogen, sulfur, and silicon atoms, preferably a divalent hydrocarbon group having 1 to 18 carbon atoms.)

[0062] In the above equation (1A), Y 1 These may independently contain a single bond or at least one selected from oxygen, nitrogen, sulfur, and silicon atoms, preferably a divalent hydrocarbon group having 1 to 18 carbon atoms, as shown below as examples. In the structure below, the bond on the left is bonded to Z, and the bond on the right is bonded to a carbon atom. [ka] [ka] [ka] [ka] [ka] [ka] (In the formula, a´ is independently an integer from 0 to 8, b and c are each an integer from 1 to 8, c´ and d´ are each an integer from 0 to 6, the sum of b and c´ is an integer from 2 to 8, and the sum of b, c, and d´ is an integer from 3 to 8. e is an integer from 1 to 9, and f is an integer from 2 to 4.)

[0063] Examples of the compound represented by formula (1A) include those shown below.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0064] Examples of the compound having a SiH group and a hydrolyzable silyl group include trimethoxysilane, triethoxysilane, triacetoxysilane, trichlorosilane, etc.

[0065] In Preparation Method 1, the amount of the compound having a SiH group and a hydrolyzable silyl group used is preferably an amount such that it is 1 to 6 moles, particularly 1.5 to 4 moles, per 1 mole of the alkenyl group in the hydrocarbon terminal group-containing compound having an alkenyl group at the terminal.

[0066] In preparation method 1, examples of hydrosilylation reaction catalysts include platinum black, chloroplatinic acid, alcohol-modified chloroplatinic acid, complexes of chloroplatinic acid with olefins, aldehydes, vinylsiloxanes, acetylene alcohols, etc., and platinum group metal catalysts such as tetrakis(triphenylphosphine)palladium and chlorotris(triphenylphosphine)rhodium. Preferably, a platinum-based compound such as a vinylsiloxane coordination compound is used. It is preferable to dissolve the platinum-based compound in a solvent such as toluene, a lower alcohol, a higher alcohol, or a silicone-based solvent before use. The amount of hydrosilylation reaction catalyst used is preferably 0.001 to 1,000 ppm, more preferably 0.01 to 100 ppm, in terms of transition metal mass, relative to the mass of the hydrocarbon terminal group-containing compound having an alkenyl group at its terminus.

[0067] In preparation method 1, a solvent can be used when carrying out the reaction. Examples of solvents 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 solvent used is preferably 0 to 1,000 parts by mass, more 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 terminus.

[0068] In preparation method 1, the reaction conditions for the hydrocarbon terminal group-containing compound having an alkenyl group at its terminus and the compound having an 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, and especially 1 to 36 hours.

[0069] In preparation method 1, if a compound having a SiH group and a hydrolyzable silyl group is used, such as trichlorosilane, in which the hydrolyzable group is a halogen group (a compound containing a SiH group and a halogenated silyl group), the substituent (halogen atom) on the silyl group can then be converted to another hydrolyzable group, such as an alkoxy group like 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, particularly 3 to 5 moles, per mole of halogen atoms in the reaction product of a hydrocarbon-terminated compound having an alkenyl group at its terminus and a compound containing a SiH group and a silyl halide group.

[0070] In preparation method 1, the reaction conditions for converting substituents (halogen atoms) on the silyl group to other hydrolyzable groups are preferably a temperature of 0 to 80°C, particularly 20 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0071] Other methods for preparing hydrocarbon terminal group-containing compounds represented by the general formula (1) of the present invention include the following: [Preparation method 2] A hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end can be mixed with a compound having a SiH group and a silyl halogenated group, and after a hydrosilylation addition reaction is carried out in the presence of a hydrosilylation catalyst, the resulting compound can be 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 the terminal end and / or a polysilazane compound which is a polymer thereof).

[0072] Here, examples of hydrocarbon terminal group-containing compounds having an alkenyl group at the terminal include those similar to those exemplified in Preparation Method 1.

[0073] Examples of compounds having an SiH group and a silyl halide group include trichlorosilane, methyldichlorosilane, dimethylchlorosilane, and tribromosilane.

[0074] In preparation method 2, the amount of compound having a SiH group and a silyl halogen 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 terminal group, similar to the compound having a SiH group and a hydrolyzable silyl group in preparation method 1.

[0075] The reaction product of a hydrocarbon terminal group-containing compound having an alkenyl group at its terminus and trichlorosilane can be prepared in the same manner as in Preparation Method 1.

[0076] In preparation method 2, the amount of ammonia gas used is preferably 1 to 300 cc / min, and more preferably 30 to 200 cc / min.

[0077] In preparation method 2, the reaction conditions for the reaction product of a hydrocarbon terminal group-containing compound having an alkenyl group at the terminal end and a compound having a SiH group and a silyl halide group, and ammonia gas are preferably at room temperature (23±15℃, the same applies hereafter), particularly 20-30℃, for 2-36 hours, particularly 4-12 hours.

[0078] Other methods for preparing hydrocarbon terminal group-containing compounds represented by the general formula (1) of the present invention include the following: [Preparation method 3] A hydrocarbon terminal group-containing compound having an NH group at its terminus can be mixed with a compound having an isocyanate group and a hydrolyzable silyl group, and reacted to produce a hydrocarbon terminal group-containing compound represented by formula (1) (particularly a compound having a hydrolyzable silyl group at its terminus via a urea bond).

[0079] Examples of hydrocarbon-terminal group-containing compounds having an NH group at the terminal end are shown below. [ka] (In the equation, x is independently the same as above.)

[0080] Examples of compounds having an isocyanate group and a hydrolyzable silyl group include (3-isocyanatopropyl)trimethoxysilane and (3-isocyanatopropyl)triethoxysilane.

[0081] In preparation method 3, the amount of compound having an isocyanate group and a hydrolyzable silyl 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 end.

[0082] In preparation method 3, a solvent can be used when carrying out the reaction. Examples of solvents include those similar to the solvent used in preparation method 1. The amount of solvent used is preferably 0 to 1,000 parts by mass, 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 the terminal end.

[0083] In preparation method 3, the reaction conditions are preferably a temperature of 0 to 100°C, particularly 20 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0084] Other methods for preparing hydrocarbon terminal group-containing compounds represented by the general formula (1) of the present invention include the following: [Preparation method 4] A hydrocarbon-terminal group-containing compound having an NH2 group at its terminus can be mixed with a compound having an isocyanate group and a hydrolyzable silyl group, and reacted to produce a hydrocarbon-terminal group-containing compound represented by formula (1) (particularly a compound having a hydrolyzable silyl group at its terminus via a urea bond).

[0085] Examples of hydrocarbon terminal group-containing compounds having an NH2 group at the terminal end are shown below. [ka] (In the equation, x and z are independently the same as above.)

[0086] Examples of compounds having an isocyanate group and a hydrolyzable silyl group include (3-isocyanatopropyl)trimethoxysilane and (3-isocyanatopropyl)triethoxysilane.

[0087] In preparation method 4, the amount of compound having an isocyanate group and a hydrolyzable silyl 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 NH2 group at the terminal.

[0088] In preparation method 4, a solvent can be used when carrying out the reaction. Examples of solvents include those similar to the solvent used in preparation method 1. The amount of solvent used is preferably 0 to 1,000 parts by mass, more preferably 50 to 200 parts by mass, per 100 parts by mass of the hydrocarbon terminal group-containing compound having an NH2 group at the terminal end.

[0089] In preparation method 4, the reaction conditions are preferably a temperature of 0 to 100°C, particularly 20 to 60°C, for 0.5 to 72 hours, and especially 1 to 36 hours.

[0090] Component (A) may include a partially reacted condensate obtained by partially condensing the reactive silyl group of the hydrocarbon terminal group-containing compound represented by formula (1) obtained as described above, using a previously known method.

[0091] [Component (B)] Component (B) is a compound having a functional group and a silanol group or a hydrolyzable silyl group at the end of its molecular chain, or a compound having a silanol group or a hydrolyzable silyl group at both ends of its molecular chain. Component (B) differs from component (A) in that it does not contain a linear, branched, or cyclic monovalent hydrocarbon group with 4 to 32 carbon atoms at the molecular chain ends other than the reactive silyl group.

[0092] In compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, the "functional group" is preferably a functional group that has adhesive properties for resin substrates. Such a functional group is preferably a monovalent group selected from amino groups, epoxy groups, thiol groups, acryloyl groups, and methacryloyl groups.

[0093] Compounds having a functional group and a silanol group or a hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or a hydrolyzable silyl group at both ends of the molecular chain, are preferably silane compounds represented by the following general formula (4). [ka] [In the formula, B is the same as in the following formulas (5a) to (5f)] [ka] (In the formula, R′ is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R'' is independently an alkyl group having 1 to 3 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) The group is one of the groups represented by (5f), where D is independently an alkylene group having 1 to 10 carbon atoms, E is independently -O-, -NH-, or -S-, R is independently an alkyl group or phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, g is an integer from 0 to 3 (however, if B is a group represented by formula (5f), g is an integer from 1 to 3), and n is an integer from 1 to 3.

[0094] In equation (4) above, B is one of the groups represented by equations (5a) to (5f) described above. Here, in formulas (5a) and (5b) above, R' is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and is preferably a hydrogen atom. Furthermore, in formula (5f) above, R'' is independently an alkyl group having 1 to 3 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3. R'' is preferably a methyl group, and X can be exemplified by the same group as X in formula (1) above, with methoxy being particularly preferred, and n is preferably 3.

[0095] Examples of such B include the following: [ka] (In the formula, h is either 0 or 1.)

[0096] In formula (4) above, D is independently an alkylene group having 1 to 10 carbon atoms, preferably 1 to 3 carbon atoms, and is preferably a methylene group, an ethylene group, or an n-propylene group.

[0097] In formula (4) above, E is independently -O-, -NH-, and -S-. E is preferably -O- and -NH-.

[0098] In formula (4) above, R is independently an alkyl group or phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3, and examples of R, X, and n are the same as those in formula (1) above. R is preferably a methyl group, X is preferably a methoxy group, and n is preferably 3. Furthermore, g is an integer between 0 and 3, preferably between 0 and 2. However, if B is a base represented by formula (5f), then g is an integer between 1 and 3, preferably 1 or 2.

[0099] Examples of compounds having a functional group and a silanol group or a hydrolyzable silyl group at the molecular chain terminus of component (B) include the following: [ka] [ka] [ka] [ka] [ka] (In the formula, h is 0 or 1, a1 is an integer from 1 to 10, preferably from 1 to 3, g is an integer from 0 to 3, g1 and g2 are each 1 or 2, and g1 + g2 is 2 or 3. Each repeating unit shown in the parentheses enclosed by g1 and g2 may be combined randomly.)

[0100] Examples of compounds having a silanol group or a hydrolyzable silyl group at both ends of the molecular chain of component (B) above include the following: [ka] (In the formula, h is 0 or 1, a1 is an integer between 1 and 10, preferably between 1 and 3, and g' is an integer between 1 and 3.)

[0101] The content of component (B) is 1 to 50% by mass of the total of components (A) and (B), preferably 2 to 45% by mass, and more preferably 2 to 40% by mass. If it is less than 1% by mass, the primer effect cannot be achieved, and if it is more than 50% by mass, the properties of component (A) (such as abrasion resistance) will be inhibited.

[0102] [Other ingredients] The surface treatment agent of the present invention may optionally contain hydrolysis condensation catalysts, such as organotin compounds (e.g., dibutyltin dimethoxide, dibutyltin dilaurate), organotitanium compounds (e.g., tetra-n-butyl titanate, tetra-n-propyl titanate), organozirconium compounds (e.g., tetra-n-butyl zirconate, tetra-n-propyl zirconate), organic acids (e.g., acetic acid, methanesulfonic acid, carboxylic acid), inorganic acids (e.g., hydrochloric acid, sulfuric acid), and organic bases (e.g., amines, trialkylamines, nitrogen-containing cyclic compounds). Among these, acetic acid, tetra-n-butyl titanate, and dibutyltin dilaurate are particularly desirable. The amount of hydrolysis condensation catalyst added is a catalytic amount, and is usually 0.001 to 5 parts by mass, particularly 0.1 to 1 part by mass, per 100 parts by mass of component (A).

[0103] Furthermore, the surface treatment agent of the present invention may also contain unreacted raw materials before the introduction of reactive groups used in the preparation of hydrocarbon terminal group-containing compounds represented by formula (1) above, and reaction intermediates produced during the preparation process.

[0104] The surface treatment agent of the present invention may contain a suitable solvent. Such solvents are preferably non-fluorinated solvents, and examples 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, methylcyclopentyl 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, etc.

[0105] The above solvents may be mixed in two or more forms, and it is preferable to uniformly dissolve components (A) and (B). The optimal concentration of components (A) and (B) to be dissolved in the solvent varies depending on the processing method, and any amount that is easy to weigh is acceptable. However, when direct coating, it is preferable to use 0.01 to 100 parts by mass, particularly 0.05 to 30 parts by mass, per 100 parts by mass of the total of components (A), components (B), and the solvent. When vapor deposition is performed, it is preferable to use 1 to 100 parts by mass, particularly 3 to 30 parts by mass, per 100 parts by mass of the total of components (A), components (B), and the solvent. In either coating case, 100 parts by mass refers to the case where no solvent is used and the coating is performed directly.

[0106] The surface treatment agent of the present invention can be applied to a substrate by known methods such as brush application, dipping, spraying, and vapor deposition. The heating method during vapor deposition can be either resistance heating or electron beam heating, and is not particularly limited. The curing conditions vary depending on the curing method, but for example, in the case of direct application (brush application, dipping, spraying, etc.), it is preferable to use a temperature of 25 to 200°C, particularly 25 to 150°C, for 30 minutes to 36 hours, and especially 1 to 24 hours. When applied by vapor deposition, it is desirable to use a temperature in the range of 20 to 200°C for 1 to 24 hours. Curing may also be performed under humid conditions.

[0107] The thickness of the cured coating is selected appropriately depending on the type of substrate, but is usually 0.1 to 100 nm, and particularly 1 to 20 nm. The thickness can be measured by methods such as spectroscopic reflectance measurement, X-ray reflectance measurement, spectroscopic ellipsometry measurement, and X-ray fluorescence measurement.

[0108] The substrate 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, resin, ceramic, and quartz. A resin substrate is particularly preferred. Examples of resins include polyethylene terephthalate (PET), polycarbonate (PC), acrylic resin (PMMA), triacetylcellulose (TAC), ABS resin, polybutylene terephthalate (PBT), polypropylene (PP), polyethylene (PE), polystyrene (PS), polyamide (PA), polyimide (PI), and silicone resin. The resin substrate also includes those having a hard coat layer, such as an acrylic hard coat layer or a silicone hard coat layer.

[0109] Furthermore, an intermediate layer may be provided on the substrate before treatment with the surface treatment agent of the present invention for the purpose of imparting another function. Examples of intermediate layers include SiO2 layers, anti-reflective layers, IR-cut filter layers, and other functional film layers, but the intermediate layer is not limited to these. In particular, an SiO2 layer can be expected to improve the strength of the substrate. Even when an intermediate layer is present on the substrate, the adhesion between the surface treatment agent of the present invention and the intermediate layer is improved, resulting in excellent abrasion resistance. The intermediate layer provided on the base material may be a single layer or two or more layers may be laminated together.

[0110] The surface treatment agent of the present invention can form a hardened film on the above-mentioned substrate, particularly a resin substrate, that exhibits high levels of water repellency, slipperiness, dirt-wiping properties, and abrasion resistance.

[0111] Articles treated with the surface treatment agent of the present invention are not particularly limited as long as water repellency is required, and can be made of the various materials described above, but articles in which at least the surface is made of resin are particularly preferred. Specific examples of articles include car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio systems, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, medical devices such as endoscopes, photocopiers, PCs, liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflective films, and other optical articles and electronic components. The surface treatment agent of the present invention can impart water repellency, slipperiness, dirt-wiping properties, and abrasion resistance to the above articles, and is therefore particularly useful as a water-repellent layer for touch panel displays, anti-reflective films, eyeglass lenses, and the like.

[0112] Furthermore, the surface treatment agent of the present invention is also useful as an antifouling coating for sanitary products such as bathtubs and washbasins, an antifouling coating for windows or tempered glass of automobiles, trains, and aircraft, an antifouling coating for headlamp covers, a water-repellent coating for exterior building materials, a stain-preventing coating for kitchen building materials, an antifouling and anti-sticker / graffiti coating for telephone booths, a coating to prevent dirt from adhering to works of art, a stain-preventing coating for compact discs and DVDs, a mold release agent or paint additive for molds, a resin modifier, a fluidity modifier or dispersibility modifier for inorganic fillers, and a lubricity enhancer for tapes, films, etc. [Examples]

[0113] The present invention will be described in more detail below with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited to the following examples. In the following examples, the molar amount of the compound is, with respect to the measured mass of the target compound, 1 The value was calculated by dividing by the molecular weight of the polymer identified by 1H-NMR analysis. Furthermore, the film thickness was measured using spectroscopic ellipsometry with a spectroscopic ellipsometer. The room temperature was 23°C.

[0114] Component (A): The following compounds (B) to (R) were synthesized as non-fluorinated hydrocarbon-terminated compounds.

[0115] [Synthesis Example 1] In the reaction vessel, the following formula (A) [ka] 1.00g of the compound represented by (1.92 × 10) -3 (mol), toluene 1.00g, (3-isocyanatopropyl)triethoxysilane 0.521g (2.11 × 10) -3 The mixture (in moles) was aged at 50°C for 24 hours. Then, the solvent and unreacted materials were removed by reduced pressure distillation to obtain 1.45 g of the product.

[0116] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (B). [ka]

[0117] [Synthesis Example 2] In the reaction vessel, the following formula (C) [ka] 1.00g (2.06 × 10) of the compound represented by [formula] -3 (mol), toluene 1.00g, trimethoxysilane 2.26g (1.84 × 10) -2mol), and 7.85×10 toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g (containing 2.43×10 -8 mol of elemental Pt) were mixed and aged at 80 °C for 24 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 1.42 g of the product.

[0118] The obtained compound 1 was confirmed by 1H-NMR to have the structure represented by the following formula (D). [Chemical formula]

[0119] [Synthesis Example 3] In a reaction vessel, 1.00 g (1.35×10 [[ID=​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​(mol), 1.00 g of toluene, 0.502 g (4.11×10 -3 mol) of trimethoxysilane, and 5.23×10 -3 g of a toluene solution of chloroplatinic acid / vinylsiloxane complex (containing 1.62×10 -8 mol of elemental Pt) were mixed and aged at 80 °C for 24 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 1.09 g of the product.

[0122] The obtained compound 1 was confirmed by 1H-NMR to have a structure represented by the following formula (H). [Chemical formula]

[0123] [Synthesis Example 5] Into a reaction vessel, 1.00 g (1.82×10 [Chemical formula] mol) of the compound represented by the following formula (I), 1.00 g of toluene, 0.668 g (5.47×10 -3 mol) of trimethoxysilane, and 6.96×10 -3 g of a toluene solution of chloroplatinic acid / vinylsiloxane complex (containing 2.15×10 -3 mol of elemental Pt) were mixed and aged at 80 °C for 24 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 1.21 g of the product. -8 mol) were mixed and aged at 80 °C for 24 hours. Then, the solvent and unreacted substances were distilled off under reduced pressure to obtain 1.21 g of the product.

[0124] The obtained compound 1 was confirmed by 1H-NMR to have a structure represented by the following formula (J). [Chemical formula]

[0125] [Synthesis Example 6] Into a reaction vessel, the following formula (K) [Chemical formula] 1.00g (1.57 × 10) of the compound represented by -3 (mol), toluene 1.00g, (3-isocyanatopropyl)trimethoxysilane 0.354g (1.73 x 10) -3 The mixture (in moles) was aged at 60°C for 24 hours. Afterward, the solvent and unreacted materials were removed under reduced pressure to obtain 1.60 g of the product.

[0126] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (L). [ka]

[0127] [Synthesis Example 7] In the reaction vessel, the following formula (M) [ka] 1.00g (2.38 × 10) of the compound represented by [formula] -3 (mol), toluene 1.00g, trimethoxysilane 0.872g (7.14 × 10) -3 9.08 × 10⁻⁶ mol) and toluene solution of chloroplatinate / vinylsiloxane complex -3 g(Pt alone: ​​2.81 × 10) -8 The mixture (containing mol) was aged at 80°C for 24 hours. After that, the solvent and unreacted substances were removed by distillation under reduced pressure to obtain 1.20 g of the product.

[0128] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (N). [ka]

[0129] [Synthesis Example 8] In the reaction vessel, the following formula (O) [ka] 1.00g of the compound represented by (1.96 × 10) -3 (mol), toluene 1.00g, trimethoxysilane 2.15g (1.76 × 10) -2 7.48 × 10⁻⁶ mol) and toluene solution of chloroplatinic acid / vinylsiloxane complex -3 g(Pt alone: ​​2.31 × 10) -8 The mixture (containing mol) was aged at 80°C for 24 hours. Afterward, the solvent and unreacted materials were removed by reduced pressure distillation to obtain 1.62 g of the product.

[0130] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (P). [ka]

[0131] [Synthesis Example 9] In the reaction vessel, the following formula (Q) [ka] 1.00g (1.29 × 10) of the compound represented by -3 (mol), toluene 1.00g, trichlorosilane 0.526g (3.88 x 10) -3 4.94 × 10⁻⁶ mol) and toluene solution of chloroplatinate / vinylsiloxane complex -3 g(Pt alone: ​​1.53 × 10) -8 The mixture (containing mol) was mixed and aged at 60°C for 24 hours. After that, the solvent and unreacted substances were removed by vacuum distillation. The obtained product was mixed with 3.00 g of toluene and aged at room temperature for 6 hours while bubbling ammonia gas (ammonia gas usage: 40 cc / min). After that, the mixture was filtered, and the solvent and unreacted substances were removed by vacuum distillation to obtain 1.10 g of product.

[0132] The resulting compound was 1 ¹H-NMR confirmed that the structure is represented by the following formula (R). [ka]

[0133] Component (B): The following compounds (b1) to (b8) were prepared as compounds having a functional group and a silanol group or a hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or a hydrolyzable silyl group at both ends of the molecular chain.

[0134] Compound (b1) [ka]

[0135] Compound (b2) [ka]

[0136] Compound (b3) [ka]

[0137] Compound (b4) [ka]

[0138] Compound (b5) [ka]

[0139] Compound (b6) [ka]

[0140] Compound (b7) [ka]

[0141] Compound (b8) [ka]

[0142] [Examples 1-12, Comparative Examples 3, 4] Compounds obtained in the synthesis examples shown in Table 1 (component (A)) and compounds having a functional group and a silanol group or hydrolyzable silyl group at the molecular chain terminus, or compounds having a silanol group or hydrolyzable silyl group at both molecular chain terminus (component (B))) were mixed in the proportions shown in Table 1. The resulting mixture was diluted with various organic solvents to prepare a surface treatment agent so that the total concentration of components (A) and (B) was as shown in Table 1 (mass%).

[0143] [Comparative Examples 1 and 2] For Comparative Examples 1 and 2, the surface treatment agents were prepared in the same manner as in the above examples, except that component (B) was not used.

[0144] [Table 1]

[0145] Formation of various cured coatings for evaluation After forming an SiO2 layer on a PET film (Kimoto Co., Ltd. hard coat film KB Stick 50S01S, test specimen substrate with a thickness of 50 μm, a width of 50 mm, and a length of 100 mm) that had been treated with a clear resin hard coat under the following conditions, the surface treatment agents prepared in the above examples and comparative examples were vacuum deposited (equipment: ULVAC KIKO, Ltd., part number: VTR-350M) (treatment conditions: pressure: 2.0 × 10⁻⁶). -2 Cured films with thicknesses of 3-5 nm for various evaluation purposes were formed by curing in an atmosphere of 80°C and 80% relative humidity for 1 hour (heating temperature: 700°C, then 25°C and 50% relative humidity for 12 hours). [SiO2 layer deposition conditions] Film deposition system: OTFC-1300 (manufactured by Optotran Co., Ltd.) Film forming material: SiO2 Deposition chamber pressure: 0.015 Pa Deposition speed: 0.8nm / s Deposition film thickness: 10nm

[0146] The films with the above-described cured coating were evaluated for water repellency, slipperiness, dirt-wiping ability, and abrasion resistance using the method shown below.

[0147] Water repellency evaluation The contact angle (hydrophobicity) of the cured film formed on the film prepared as described above was measured using a Drop Master contact angle meter (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25°C, relative humidity: 40%). The measurement involved capturing a photograph of the droplet 1 second after dropping using a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software included 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. The results are shown in Table 2. In this invention, a good (water-repellent) water contact angle is defined as 90° or more (the same applies hereinafter). [Analysis conditions] Method: Droplet method (θ / 2 method) Droplet recognition: automatic Droplet detection line (distance from needle tip): 50 dots Algorithm: Automatic Image Mode: Frame Threshold level: Automatic

[0148] Evaluation of slipperiness The kinetic friction coefficient of the film with the cured coating prepared as described above was evaluated for its slipperiness by the method shown below. The kinetic friction coefficient of the film with the cured coating on the nonwoven fabric was measured in accordance with ASTM D1894 using a surface properties measuring instrument TYPE:14FW (manufactured by Shinto Kagaku Co., Ltd.) under conditions of a load of 100 gf and a tensile speed of 500 mm / min. The results (kinetic friction coefficient) are shown in Table 2. [Conditions for evaluating slipperiness] Load: 100gf Stroke: 100mm Contact area: 1 x 3cm 2 Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation)

[0149] Evaluation of dirt-removing properties The film with the cured coating prepared as described above was then used to draw a 2cm straight line with a Hi-Mackie (manufactured by Zebra), after which the ink was allowed to dry and wiped off with tissue paper. The number of rubs required to remove the ink was evaluated according to the following criteria. The results are shown in Table 2. [Criteria for evaluating dirt-removing properties] A: Number of rubs: 4 times or less B: More than 5 rubs C: The ink won't come off.

[0150] Evaluation of wear resistance The film with the cured coating prepared as described above was rubbed every 500 times using a rubbing tester (manufactured by Shinto Kagaku Co., Ltd.) under the following conditions. The contact angle (water repellency) of the cured coating with respect to water was measured in the same manner as described above, and the number of times the contact angle fell below 80° was counted to evaluate the abrasion resistance. The test environment conditions were 25°C and 40% relative humidity. The results (number of times the water contact angle fell below 80°) are shown in Table 2. [Fabric abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1cm 2 Distance traveled (one way): 40mm Traveling speed: 4,800mm / min Load: 500gf

[0151] As shown in Table 2, the cured films of the surface treatment agents in Examples 1 to 12 exhibited water repellency due to the presence of hydrocarbon chains with a predetermined number of carbon atoms due to component (A), and improved molecular mobility, resulting in slipperiness and dirt-wiping properties. Furthermore, the presence of component (B) improved adhesion to the substrate, resulting in excellent abrasion resistance. The cured films of the surface treatment agents in Comparative Examples 1 and 2 did not contain component (B), resulting in poor adhesion to the substrate and inferior abrasion resistance. The cured film of the surface treatment agent in Comparative Example 3 contained component (B), but the content was low, resulting in poor abrasion resistance and failure to exhibit its properties. The cured film of the surface treatment agent in Comparative Example 4 had too high a content of component (B), which inhibited the properties of component (A), preventing the initial properties (slipperiness and dirt-wiping properties) from being exhibited, and also reducing substrate adhesion (abrasion resistance). As described above, the surface treatment agents in the examples made it possible to obtain a cured film of a non-fluorine-based surface treatment agent that exhibits high levels of water repellency, slipperiness, dirt-wiping properties, and abrasion resistance in vapor deposition coating.

[0152] [Table 2]

[0153] [Examples 13-20, Comparative Examples 7, 8] Compounds obtained in the synthesis examples shown in Table 3 (component (A)) and compounds having a functional group and a silanol group or hydrolyzable silyl group at the molecular chain termini, or compounds having silanol groups or hydrolyzable silyl groups at both molecular chain termini (component (B))) were mixed in the proportions shown in Table 3. The resulting mixture was diluted with various organic solvents to prepare a surface treatment agent so that the total concentration of components (A) and (B) was as shown in Table 3 (mass%).

[0154] [Comparative Examples 5 and 6] For Comparative Examples 5 and 6, the surface treatment agents were prepared in the same manner as in the above examples, except that component (B) was not used.

[0155] [Table 3]

[0156] Formation of various cured coatings for evaluation A PET film treated with a clear resin hard coat (Kimoto Co., Ltd.'s hard coat film KB Stick 50S01S, test specimen substrate with a thickness of 50 μm, a width of 50 mm, and a length of 100 mm) was spray-coated with each of the surface treatment agents prepared in the above examples and comparative examples under the following conditions. The coatings were then cured at 25°C and 50% relative humidity for 30 minutes in an atmosphere of 80°C and 80% relative humidity to form various evaluation cured films with a thickness of 3 to 5 nm. [Spray Coat Conditions] Ambient temperature: 25℃ / 50% Nozzle distance: 50mm Air pressure: 150kPa Speed: 300mm / min Pitch: 5mm

[0157] The films with the above-described cured coating were evaluated for water repellency, slipperiness, dirt-wiping ability, and abrasion resistance using the method shown below.

[0158] Water repellency evaluation The contact angle (hydrophobicity) of the cured film formed on the film prepared as described above was measured using a Drop Master contact angle meter (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25°C, relative humidity: 40%). The measurement involved capturing a photograph of the droplet 1 second after dropping using a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software included 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. The results are shown in Table 4. [Analysis conditions] Method: Droplet method (θ / 2 method) Droplet recognition: automatic Droplet detection line (distance from needle tip): 50 dots Algorithm: Automatic Image Mode: Frame Threshold level: Automatic

[0159] Evaluation of slipperiness The kinetic friction coefficient of the film with the cured coating prepared as described above was evaluated for its slipperiness by the method shown below. The kinetic friction coefficient of the film with the cured coating on the nonwoven fabric was measured in accordance with ASTM D1894 using a surface properties measuring instrument TYPE:14FW (manufactured by Shinto Kagaku Co., Ltd.) under conditions of a load of 100 gf and a tensile speed of 500 mm / min. The results (kinetic friction coefficient) are shown in Table 4. [Conditions for evaluating slipperiness] Load: 100gf Stroke: 100mm Contact area: 1 x 3cm 2 Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation)

[0160] Evaluation of dirt-removing properties The film with the cured coating prepared as described above was then used to draw a 2cm straight line with a Hi-Mackie (manufactured by Zebra), after which the ink was allowed to dry and wiped off with tissue paper. The number of rubs required to remove the ink was evaluated according to the following criteria. The results are shown in Table 4. [Criteria for evaluating dirt-removing properties] A: Number of rubs: 4 times or less B: More than 5 rubs C: The ink won't come off.

[0161] Evaluation of wear resistance The film with the cured coating prepared as described above was rubbed every 500 times using a rubbing tester (manufactured by Shinto Kagaku Co., Ltd.) under the following conditions. The contact angle (water repellency) of the cured coating with water was measured in the same manner as described above, and the number of times the water contact angle fell below 80° was counted to evaluate the abrasion resistance. The test environment conditions were 25°C and 40% relative humidity. The results (number of times the water contact angle fell below 80°) are shown in Table 4. [Fabric abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1cm 2 Distance traveled (one way): 40mm Traveling speed: 4,800mm / min Load: 500gf

[0162] As shown in Table 4, the cured films of the surface treatment agents in Examples 13-20 exhibited water repellency due to the presence of hydrocarbon chains with a predetermined number of carbon atoms due to component (A), and improved molecular mobility, resulting in slipperiness and dirt-wiping properties. Furthermore, the presence of component (B) improved adhesion to the substrate, resulting in excellent abrasion resistance. The cured films of the surface treatment agents in Comparative Examples 5 and 6 did not contain component (B), resulting in poor adhesion to the substrate and inferior abrasion resistance. The cured film of the surface treatment agent in Comparative Example 7 contained component (B), but the content was low, resulting in poor abrasion resistance and failure to exhibit its properties. The cured film of the surface treatment agent in Comparative Example 8 had too high a content of component (B), which inhibited the properties of component (A), preventing the initial properties (slipperiness and dirt-wiping properties) from being exhibited, and also reducing substrate adhesion (abrasion resistance). As described above, the surface treatment agents in the examples made it possible to obtain a cured film of a non-fluorine-based surface treatment agent that exhibits high levels of water repellency, slipperiness, dirt-wiping properties, and abrasion resistance when applied by spray coating.

[0163] [Table 4]

[0164] [Examples 21-25, Comparative Examples 11, 12] The compounds obtained in the synthesis examples shown in Table 5 (component (A)) and compounds having a functional group and a silanol group or hydrolyzable silyl group at the molecular chain termini, or compounds having silanol groups or hydrolyzable silyl groups at both molecular chain termini (component (B))) were mixed in the proportions shown in Table 5. The resulting mixture was diluted with various organic solvents to prepare a surface treatment agent so that the total concentration of components (A) and (B) was as shown in Table 5 (by mass%).

[0165] [Comparative Examples 9 and 10] For Comparative Examples 9 and 10, the surface treatment agents were prepared in the same manner as in the above examples, except that component (B) was not used.

[0166] [Table 5]

[0167] Formation of various cured coatings for evaluation After forming an anti-reflective layer on a PET film (Kimoto Co., Ltd. hard coat film KB Stick 50S01S, 50 μm thick, 50 mm wide, 100 mm long test specimen substrate) that had been treated with a clear resin hard coat under the following conditions, the surface treatment agents prepared in the above examples and comparative examples were vacuum-deposited (equipment: ULVAC KIKO, Ltd., part number: VTR-350M) (treatment conditions: pressure: 2.0 × 10⁻⁶). -2 Cured films with thicknesses of 3-5 nm for various evaluation purposes were formed by curing in an atmosphere of 80°C and 80% relative humidity for 1 hour (heating temperature: 700°C, then 25°C and 50% relative humidity for 12 hours).

[0168] [Formation of anti-reflective layer] An anti-reflective layer with the film thickness configuration shown in Table 6 below was deposited on the surface of a glass substrate that had been alkaline-cleaned using a sputtering deposition apparatus under the following conditions. SiO2 was deposited as the low refractive index layer, and Nb2O5 as the high refractive index layer. Oxygen plasma irradiation was performed before depositing the anti-reflective layer. The deposition rate for SiO2 was 0.3 nm / second, and the deposition rate for Nb2O5 was 0.4 nm / second. The film thickness of each layer was controlled by the deposition time.

[0169] [Table 6]

[0170] [Anti-reflection layer deposition conditions] Thin film deposition system: RAS-1100B (manufactured by Synchron) Oxygen plasma irradiation conditions during substrate pretreatment Oxygen gas flow rate: 70 sccm (Standard Cubic Centimeters) Argon gas flow rate: 100 sccm Deposition chamber pressure: 0.1 Pa RF supply power: 3000W Processing time: 50 seconds Low refractive index layer deposition conditions Target material: Silicon Argon gas flow rate: 100 sccm Deposition chamber pressure: 0.1 Pa RF supply power: 8000W Deposition speed: 0.3nm / s Oxygen plasma irradiation conditions during low refractive index layer deposition Oxygen gas flow rate: 70 sccm RF supply power: 3000W High refractive index layer deposition conditions Target material: Niobium Argon gas flow rate: 100 sccm Deposition chamber pressure: 0.1 Pa RF supply power: 5000W Deposition speed: 0.4nm / s Oxygen plasma irradiation conditions during high refractive index layer deposition Oxygen gas flow rate: 70 sccm RF supply power: 3000W

[0171] The films with the above-described cured coating were evaluated for water repellency, slipperiness, dirt-wiping ability, and abrasion resistance using the method shown below.

[0172] Water repellency evaluation The contact angle (hydrophobicity) of the cured film formed on the film prepared as described above was measured using a Drop Master contact angle meter (DMo-701SA, manufactured by Kyowa Interface Science Co., Ltd.) (droplet: 2 μl, temperature: 25°C, relative humidity: 40%). The measurement involved capturing a photograph of the droplet 1 second after dropping using a CCD camera connected to the contact angle meter, and then analyzing the droplet image using FAMAS, the contact angle analysis software included 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. The results are shown in Table 7. [Analysis conditions] Method: Droplet method (θ / 2 method) Droplet recognition: automatic Droplet detection line (distance from needle tip): 50 dots Algorithm: Automatic Image Mode: Frame Threshold level: Automatic

[0173] Evaluation of slipperiness The kinetic friction coefficient of the film with the cured coating prepared as described above was evaluated for its slipperiness by the method shown below. The kinetic friction coefficient of the film with the cured coating on the nonwoven fabric was measured in accordance with ASTM D1894 using a surface properties measuring instrument TYPE:14FW (manufactured by Shinto Kagaku Co., Ltd.) under conditions of a load of 100 gf and a tensile speed of 500 mm / min. The results (kinetic friction coefficient) are shown in Table 7. [Conditions for evaluating slipperiness] Load: 100gf Stroke: 100mm Contact area: 1 x 3cm 2 Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation)

[0174] Evaluation of dirt-removing properties The film with the cured coating prepared as described above was then used to draw a 2cm straight line with a Hi-Mackie (manufactured by Zebra), after which the ink was allowed to dry and wiped off with tissue paper. The number of rubs required to remove the ink was evaluated according to the following criteria. The results are shown in Table 7. [Criteria for evaluating dirt-removing properties] A: Number of rubs: 4 times or less B: More than 5 rubs C: The ink won't come off.

[0175] Evaluation of wear resistance The film with the cured coating prepared as described above was rubbed every 500 times using a rubbing tester (manufactured by Shinto Kagaku Co., Ltd.) under the following conditions. The contact angle (water repellency) of the cured coating with water was measured in the same manner as described above, and the number of times the water contact angle fell below 80° was counted to evaluate the abrasion resistance. The test environment conditions were 25°C and 40% relative humidity. The results (number of times the water contact angle fell below 80°) are shown in Table 7. [Fabric abrasion resistance test conditions] Nonwoven fabric: BEMCOT (manufactured by Asahi Kasei Corporation) Contact area: 1cm 2 Distance traveled (one way): 40mm Traveling speed: 4,800mm / min Load: 500gf

[0176] As shown in Table 7, the cured films of the surface treatment agents in Examples 21-25 exhibited water repellency due to the presence of hydrocarbon chains with a predetermined number of carbon atoms due to component (A), and improved molecular mobility, resulting in slipperiness and dirt-wiping properties. Furthermore, the inclusion of component (B) improved adhesion to the substrate, demonstrating excellent abrasion resistance. The cured films of the surface treatment agents in Comparative Examples 9 and 10 did not contain component (B), resulting in poor adhesion to the substrate and inferior abrasion resistance. The cured film of the surface treatment agent in Comparative Example 11 contained component (B), but the content was low, resulting in poor abrasion resistance and failure to exhibit its properties. The cured film of the surface treatment agent in Comparative Example 12 had too high a content of component (B), which inhibited the properties of component (A), preventing the initial properties (slipperiness and dirt-wiping properties) from being exhibited, and also reducing substrate adhesion (abrasion resistance). As described above, the surface treatment agents in the examples made it possible to obtain a cured film of a non-fluorine-based surface treatment agent that exhibits high levels of water repellency, slipperiness, dirt-wiping properties, and abrasion resistance in vapor deposition coating.

[0177] [Table 7]

Claims

1. (A) Nonfluorine-based hydrocarbon-end group-containing compounds and / or partially reaction condensates thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, (B) Compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or hydrolyzable silyl group at both ends of the molecular chain: 1 to 50% by mass of the total of components (A) and (B) A non-fluorine-based surface treatment agent containing [specific component].

2. The surface treatment agent according to claim 1, wherein the monovalent hydrocarbon group in the hydrocarbon terminal group-containing compound of component (A) is a group selected from C6-C32 alkyl groups and C6-C32 aryl groups.

3. The surface treatment agent according to claim 1, wherein the hydrocarbon terminal group-containing compound of component (A) has two or more monovalent hydrocarbon groups and has a trivalent or higher linking group that bonds the two or more monovalent hydrocarbon groups to at least one reactive silyl group.

4. The hydrocarbon terminal group-containing compound of component (A) is of the following general formula (1) 【Chemistry 1】 [In the formula, R 1 R may independently contain at least one selected from oxygen, sulfur, nitrogen, and silicon atoms, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 4 to 32 carbon atoms, 2 A is a hydrogen atom, halogen atom, hydroxyl group, siloxy group, amino group, thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U is a carbon atom, silicon atom, nitrogen atom, or a trivalent or tetravalent organic group; V is independently a single bond or a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, and sulfur atoms; Z is independently a single bond, carbon atom, silicon atom, nitrogen atom, sulfur atom, or a trivalent to octavalent organic group; Y is independently a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, sulfur, and silicon atoms; and A is independently the following general formula (2) 【Chemistry 2】 (In the formula, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) Or the following general formula (3) 【Transformation 3】 (In the formula, n'' is a number between 0 and 3, and n'' is (3 - n'') / 2.) The base is represented by , where k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is an integer from 1 to 3, k1 + k2 + k3 is 3 or 4, and m is an integer from 1 to 7. The surface treatment agent according to claim 1, which is a hydrocarbon terminal group-containing compound represented by [the specified compound].

5. The surface treatment agent according to claim 4, wherein k1 is 2 or 3 in formula (1) above.

6. In the above formula (1), R 1 However, the following formula 【Chemistry 4】 (In the formula, R A Q is independently a monovalent hydrocarbon group having 4 to 32 carbon atoms, which may be linear, branched, cyclic, or a combination thereof, and Q is independently an oxygen atom, a sulfur atom, a divalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a diorganosilylene group, a sylalkylene structure or sylarylene structure, and a linear or branched or cyclic divalent organopolysiloxane residue having 2 to 10 silicon atoms, or having 3 to 10 silicon atoms, a carbonyl (ketone) group, an ester group, a carbonate group, a sulfinyl group, a sulfonyl group, a thioester group, a thiocarbonate group, a thiocarbamate group, an amino group, an amide group, or a carbamate Q' is a divalent group selected from the group consisting of a group, a urea group, and a divalent nitrogen-containing heterocyclic group, Q' is independently a trivalent group selected from the group consisting of a nitrogen atom, a trivalent cyclic hydrocarbon group having 6 to 8 carbon atoms, a linear or branched or cyclic trivalent organopolysiloxane residue having 2 to 10 silicon atoms, a trivalent amide group, and a trivalent nitrogen-containing heterocyclic group, Q'' is independently a tetravalent group selected from the group consisting of a silicon atom, a tetravalent cyclic hydrocarbon group having 6 to 8 carbon atoms, and a linear or branched or cyclic tetravalent organopolysiloxane residue having 2 to 10 silicon atoms, R B R is a divalent hydrocarbon group having 1 to 29 carbon atoms, which may be independently single-bonded, linear, branched, or cyclic, C R is independent A (or a hydrogen atom, where p is an integer between 0 and 10. However, the total number of carbon atoms in each structure is 32 or less.) The surface treatment agent according to claim 4, wherein the group is any of the groups represented by the following:

7. In the above formula (1), R 1 The surface treatment agent according to claim 4, wherein the group may independently contain at least one selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 11 to 32 carbon atoms.

8. The surface treatment agent according to claim 4, wherein in formula (1) above, Y is a group selected from the group consisting of an alkylene group having 1 to 20 carbon atoms which may contain at least one selected from oxygen atoms, nitrogen atoms and sulfur atoms, an alkylene group having 1 to 10 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 bonded to each other via a diorganosilylene group, a sylalkylene structure, a sylarylene structure or a nitrogen-containing heterocyclic group, and a divalent group in which an alkylene group having 1 to 10 carbon atoms is bonded to the binding site of a linear organopolysiloxane residue having 2 to 10 silicon atoms or a branched or cyclic organopolysiloxane residue having 3 to 10 silicon atoms.

9. In the above formula (1), Z is a single bond, 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, -SiR 3 = (R 3 is a trivalent group represented by a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms), -CR 4 = (R 4 is a trivalent group represented by 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 or a branched or cyclic trivalent to octavalent 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-containing group, and the surface treatment agent according to claim 4, which is a trivalent to octavalent group selected from the group consisting of

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

11. The surface treatment agent according to claim 1, wherein the functional group of the compound having a functional group and a silanol group or a hydrolyzable silyl group at the molecular chain terminus of component (B) is an amino group, an epoxy group, a thiol group, an acryloyl group, or a methacryloyl group.

12. A compound having a functional group and a silanol group or a hydrolyzable silyl group at the end of the molecular chain of component (B), or a compound having a silanol group or a hydrolyzable silyl group at both ends of the molecular chain, is given by the following general formula (4) 【Transformation 5】 [In the formulas, B is the same as in the following formulas (5a) to (5f)] 【Transformation 6】 (In the formula, R' is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R'' is independently an alkyl group having 1 to 3 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) The group is one of the groups represented by (5f), where D is independently an alkylene group having 1 to 10 carbon atoms, E is independently -O-, -NH-, or -S-, R is independently an alkyl group or phenyl group having 1 to 4 carbon atoms, X is independently a hydroxyl group or a hydrolyzable group, g is an integer from 0 to 3 (however, if B is a group represented by formula (5f), g is an integer from 1 to 3), and n is an integer from 1 to 3. The surface treatment agent according to claim 1, which is a silane compound represented by [the specified compound].

13. An article surface-treated with the surface treatment agent described in any one of claims 1 to 12.

14. The article according to claim 13, wherein at least one surface of the article is made of resin.

15. A method for forming a film by applying a surface treatment agent to a substrate, wherein the surface treatment agent is (A) Nonfluorine-based hydrocarbon-end group-containing compounds and / or partially reaction condensates thereof, having at least one linear, branched, or cyclic monovalent hydrocarbon group having 4 to 32 carbon atoms at one end of the molecular chain and at least one reactive silyl group at the other end of the molecular chain, (B) Compounds having a functional group and a silanol group or hydrolyzable silyl group at the end of the molecular chain, or compounds having a silanol group or hydrolyzable silyl group at both ends of the molecular chain: 1 to 50% by mass of the total of components (A) and (B) A method for forming a coating using a non-fluorine-based surface treatment agent.

16. The method for forming a film according to claim 15, wherein the monovalent hydrocarbon group in the hydrocarbon terminal group-containing compound of component (A) is a group selected from C6-C32 alkyl groups and C6-C32 aryl groups.

17. The method for forming a film according to claim 15, wherein the hydrocarbon terminal group-containing compound of component (A) has two or more monovalent hydrocarbon groups and has a trivalent or higher linking group that bonds the two or more monovalent hydrocarbon groups to at least one reactive silyl group.

18. The hydrocarbon terminal group-containing compound of component (A) is of the following general formula (1) 【Transformation 7】 [In the formula, R 1 R may independently contain at least one selected from oxygen, sulfur, nitrogen, and silicon atoms, and may be linear, branched, cyclic, or a combination thereof, and is a monovalent hydrocarbon group having 4 to 32 carbon atoms, 2 A is a hydrogen atom, halogen atom, hydroxyl group, siloxy group, amino group, thiol group, or a monovalent hydrocarbon group having 1 or 2 carbon atoms; U is a carbon atom, silicon atom, nitrogen atom, or a trivalent or tetravalent organic group; V is independently a single bond or a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, and sulfur atoms; Z is independently a single bond, carbon atom, silicon atom, nitrogen atom, sulfur atom, or a trivalent to octavalent organic group; Y is independently a divalent hydrocarbon group which may contain at least one selected from oxygen, nitrogen, sulfur, and silicon atoms; and A is independently the following general formula (2) 【Transformation 8】 (In the formula, R is independently an alkyl group having 1 to 4 carbon atoms or a phenyl group, X is independently a hydroxyl group or a hydrolyzable group, and n is an integer from 1 to 3.) Or the following general formula (3) 【Chemistry 9】 (In the formula, n'' is a number between 0 and 3, and n'' is (3 - n'') / 2.) The base is represented by , where k1 is an integer from 1 to 3, k2 is 0 or 1, k3 is an integer from 1 to 3, k1 + k2 + k3 is 3 or 4, and m is an integer from 1 to 7. A method for forming a coating according to any one of claims 15 to 17, wherein the compound is a hydrocarbon terminal group-containing compound represented by [the compound name].

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