Compound, method for producing compound, composition, surface treatment agent, article, and method for producing article

Abstract

Provided are a compound capable of forming a surface treatment layer with excellent abrasion resistance, a composition and a surface treatment agent, an article comprising a surface treatment layer with excellent abrasion resistance, and methods for producing the compound and the article.　The compound is represented by the following formula:　R11 4-m1-m2Si-[Q11(SiR1 2-O)p1-SiR1 2-Z1-Q1[Z2-Si(R3)nL1 3-n]q1]m1{Q11(SiR1 2-O)p1-SiR11 3-m3[Q11(SiR1 2-O)p1-SiR1 2-Z1-Q1[Z2-Si(R3)nL1 3-n]q1]m3}m2 Symbols used in the above equation are as defined in the specification.

Description

Compound, Method for Producing the Compound, Composition, Surface Treatment Agent, Article, and Method for Producing the Article

[0001] The present disclosure relates to a compound, a method for producing the compound, a composition, a surface treatment agent, an article, and a method for producing the article.

[0002] In recent years, techniques for making fingerprints less likely to adhere to the surface of optical articles and techniques for making dirt easier to remove in order to improve appearance and visibility have become widespread in glasses lenses, wearable terminals, touch panel displays, and the like. As a specific method for improving performance such as appearance and visibility, a method of performing surface treatment using a surface treatment agent on the surface of an article is known.

[0003] For example, Patent Document 1 describes a composition containing a divalent linear organopolysiloxane group and a specific compound having a hydrolyzable group.

[0004] International Publication No. 2021 / 187184

[0005] Further improvement in wear resistance is required for the surface treatment agent.

[0006] The present disclosure has been made in view of such circumstances, and an object thereof is to provide a compound, a composition, and a surface treatment agent capable of forming a surface treatment layer excellent in wear resistance, an article provided with a surface treatment layer excellent in wear resistance, and methods for producing the compound and the article.

[0007] The present disclosure includes the following aspects. [1] A compound represented by the following formula (1). R １１ , ２ , ｑ１ , ｐ１ , １ , １ , ３ , １ , １１ , ２ , １ , １ ,<0​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​３－ｍ３ [Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ３} ｍ２ …(1) However, R １１ Each of these is independently a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue, Q １１ Each is independently an oxygen atom or a hydrocarbon group, and R １ Each of these is independently a hydrocarbon group, Z １ Each of these is an alkylene group which may have a divalent group between carbon atoms, Q １ Z is a single bond or a (1+q1) valence linking group. ２ Each of these is an alkylene group which may have a single bond or a divalent group between carbon atoms, R ３ Each of these is independently a hydrocarbon group, L １ Each is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, each is independently an integer from 0 to 2, each is independently an integer of 0 or more, each is independently an integer from 1 to 3, each is independently an integer from 1 to 4, each is independently an integer from 0 to 4, each is independently an integer from 0 to 3, and each is m1 + m3 (however, if there are multiple m3s, the sum of all m3s) is an integer of 3 or more. [2] The compound according to [1], wherein the p1 is an integer from 0 to 4. [3] The Z １ The compound described in [1] or [2], wherein the alkylene group has 11 or more carbon atoms. [4] A method for producing the compound described in any one of [1] to [3], comprising reacting a compound represented by the following formula (1-1) with a compound represented by the following formula (1-2) to obtain compound (1-3). R１１ ４－ｍ１－ｍ２ Si—[Q １１ (SiR １ ２ —O) ｐ１ H] ｍ１ {Q １１ (SiR １ ２ —O) ｐ１ —SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ —O) ｐ１ H] ｍ２ …(1-1) X １ —SiR １ ２ —Z １２ —X ２ …(1-2) R １１ ４－ｍ１－ｍ２ Si—[Q １１ (SiR １ ２ —O) ｐ１ —SiR １ ２ —Z １２ —X ２ ｍ１ {Q １１ (SiR １ ２ —O) ｐ１ —SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ —O) ｐ１ —SiR １ ２ —Z １２ —X ２ ｍ２ …(1-3) However, R １１ is a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue, Q １１ is each independently an oxygen atom or a hydrocarbon group, R １ is each independently a hydrocarbon group, Z １２ is each independently an alkylene group which may have a divalent group between carbon atoms, X<00001{02}is a hydroxyl group or a halogen atom, X​​２ is a group having a carbon-carbon double bond, or X １ A halogen atom different from the one described above, where p1 is an integer of 0 or more, q1 is an integer from 1 to 3, m1 is an integer from 1 to 4, m2 is an integer from 0 to 4, m3 is an integer from 0 to 3, and m1 + m3 (however, if there are multiple m3s, the sum of all m3s) is an integer of 3 or more. [5] A composition comprising the compound described in any one of [1] to [3] and a liquid medium. [6] A composition comprising the compound described in any one of [1] to [3] and another compound having a reactive silyl group. [7] A surface treatment agent comprising the compound described in any one of [1] to [3]. [8] A surface treatment agent comprising the compound described in any one of [1] to [3] and a liquid medium. [9] A surface treatment agent comprising the compound described in any one of [1] to [3] and another compound having a reactive silyl group.

[10] An article comprising a base material and a surface treatment layer disposed on the base material and surface-treated with a surface treatment agent containing a compound described in any one of [1] to [3].

[11] An article according to

[10] which is an optical member.

[12] An article according to

[10] or

[11] which is a display or touch panel.

[13] A method for manufacturing an article, comprising surface-treating a base material with a surface treatment agent containing a compound described in any one of [1] to [3] to produce an article in which a surface treatment layer is formed on the base material.

[0008] This disclosure provides compounds, compositions, and surface treatment agents capable of forming a surface treatment layer with excellent wear resistance, articles comprising a surface treatment layer with excellent wear resistance, and methods for manufacturing the compounds and articles.

[0009] The embodiments for carrying out the embodiments of this disclosure will be described in detail below. However, the embodiments of this disclosure are not limited to the embodiments described below. In the embodiments described below, the components (including elemental steps, etc.) are not essential unless otherwise specified. The same applies to numerical values ​​and their ranges, and do not limit the embodiments of this disclosure.

[0010] In this disclosure, the term "process" includes not only processes that are independent of other processes, but also processes that cannot be clearly distinguished from other processes, provided that the purpose of the process is achieved. In this disclosure, numerical ranges indicated using "~" include the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described in stages in this disclosure, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Also, in numerical ranges described in this disclosure, the upper or lower limit of that numerical range may be replaced with the values ​​shown in the examples. In this disclosure, each component may contain multiple types of the corresponding substance. If multiple types of the substance corresponding to each component are present in the composition, the content or amount of each component means the total content or amount of the multiple types of substances present in the composition, unless otherwise specified. In this disclosure, "surface treatment layer" means a layer formed on the surface of the substrate by surface treatment. In this disclosure, when a compound or group is represented by a specific formula (X), the compound or group represented by formula (X) may be referred to as compound (X) or compound X, and group (X) or group X, respectively. In this disclosure, organo(poly)siloxane residue means organosiloxane residue or organopolysiloxane residue. In this disclosure, "Me" may mean a methyl group, and "Et" may mean an ethyl group. In this disclosure, when there are multiple identical symbols in a single chemical formula, such identical symbols may represent the same structure or may represent different structures within a defined range.

[0011] [Compound] The compound of this disclosure is a compound represented by formula (1), which will be described later. Compound (1) has a structure of three or more "alkyl chain-reactive silyl groups" via branched organopolysiloxane residues. It is presumed that a surface treatment layer formed using such compound (1) will have alkyl chains packing together intramolecularly and / or intermolecularly, and that the reactive silyl groups will be densely arranged and adhere closely to the substrate. Thus, a surface treatment layer formed using this compound has excellent abrasion resistance. The compound of this disclosure will be described in detail below.

[0012] <Compound (1)> Compound (1) is represented by the following formula (1). R １１ ４－ｍ１－ｍ２ Si-[Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ１ {Q １１ (SiR １ ２ -O) ｐ１ -SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ３} ｍ２ …(1) However, R １１ Each of these is independently a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue, Q １１ Each is independently an oxygen atom or a hydrocarbon group, and R １ Each of these is independently a hydrocarbon group, Z １ Each of these is an alkylene group which may have a divalent group between carbon atoms, Q １ Z is a single bond or a (1+q1) valence linking group. ２ Each of these is an alkylene group which may have a single bond or a divalent group between carbon atoms, R ３ Each of these is independently a hydrocarbon group, L １Each of the following is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; each of the following is independently an integer from 0 to 2; each of the following is independently an integer of 0 or more; each of the following is independently an integer from 1 to 3; each of the following is independently an integer from 1 to 4; each of the following is independently an integer from 0 to 4; each of the following is independently an integer from 0 to 3; and each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 2: each of the following is independently an integer from 0 to 2: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 4

[0013] R １１ R is a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue. １１ The hydrocarbon group can be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred and an alkyl group being more preferred. The alkyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. From the viewpoint of improving liquid repellency, a linear alkyl group or a branched alkyl group is preferred, with a linear alkyl group being more preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of alkyl groups include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group, from the viewpoint of further improving liquid repellency, a methyl group or an ethyl group is preferred, with a methyl group being more preferred.

[0014] R １１ The alkyl group in the trialkylsilyl group is the same as the alkyl group described above, and from the viewpoint of improving liquid repellency, a linear alkyl group or a branched alkyl group is preferred, and a linear alkyl group is more preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of the trialkylsilyl group include the trimethylsilyl group, the triethylsilyl group, and the tert-butyldimethylsilyl group, with the trimethylsilyl group being preferred.

[0015] R １１ The organopolysiloxane residues include groups represented by the following formulas (1a), (1b), or (1c). ２１ ３ Si-Q ２１ - (1a)

[0016] However, R ２１ Each of these independently comprises a hydrocarbon group, or R ２１ａ ３ Si-R ２２ａ - and R ２１ａ Each of these independently comprises a hydrocarbon group, or R ２１ｂ ３ Si-R ２２ｂ - and R ２１ｂ Each of these independently comprises a hydrocarbon group, or R ２１ｃ ３ Si-R ２２ｃ - and R ２１ｃ Each of these independently comprises a hydrocarbon group, or R ２１ｄ ３ Si-R ２２ｄ - and R ２１ｄ Each of these is independently a hydrocarbon group, and R ２２ａ , R ２２ｂ , R ２２ｃ , R ２２ｄ Each of these is independently a -O- or an alkylene group having 1 to 6 carbon atoms, Q ２１ R is -O-, -C(=O)-, or an alkylene group having 1 to 6 carbon atoms. ２３ Each of these is independently a hydrocarbon group, Q ２２ is -O-, -C(=O)-, or an alkylene group having 1 to 6 carbon atoms, t1 is an integer from 1 to 5, and R ２４ Each of these is independently a hydrocarbon group, Q ２３ This is a -O-, -C(=O)-, or an alkylene group having 1 to 6 carbon atoms.

[0017] R ２１ , R ２１ａ , R ２１ｂ , R ２１ｃ , R ２１ｄ , R ２３ and R ２４The hydrocarbon group in this material can be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred and an alkyl group being more preferred. The alkyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. From the viewpoint of improving liquid repellency, a linear alkyl group or a branched alkyl group is preferred, with a linear alkyl group being more preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of hydrocarbon groups include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group, from the viewpoint of further improving liquid repellency, a methyl group or an ethyl group is preferred, with a methyl group being more preferred.

[0018] R ２２ａ , R ２２ｂ , R ２２ｃ , R ２２ｄ Q ２１ Q ２２ and Q ２３ In this formula, linear alkylene groups with 1 to 6 carbon atoms are preferred. Specific examples of alkylene groups with 1 to 6 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, and hexylene groups.

[0019] t1 is an integer from 1 to 5, preferably from 1 to 4, and more preferably from 1 to 3.

[0020] R of base (1a) ２１ ３ Specific examples of Si- are listed below. However, * represents Q. ２１ This is the connection point.

[0021]

[0022] Q of the base (1b) ２２ Specific examples of substructures excluding the following are listed below. However, * represents Q. ２２ This is the connection point.

[0023]

[0024] Q of the base (1c) ２３ Specific examples of substructures excluding the following are listed below. However, * represents Q. ２３This is the connection point.

[0025]

[0026] Q １１ Examples of hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups, with aliphatic hydrocarbon groups being preferred and alkylene groups being more preferred. The alkylene group may be a linear alkylene group, a branched alkylene group, or a cyclic alkylene group. From the viewpoint of ease of manufacture and improved liquid repellency, a linear alkylene group is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 2. Specific examples of alkylene groups include methylene groups, ethylene groups, propylene groups, butylene groups, pentylene groups, and hexylene groups, with methylene groups or ethylene groups being preferred and methylene groups being more preferred.

[0027] R １ The hydrocarbon group is the above R ２１ Examples of hydrocarbon groups similar to those in the above are included. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of hydrocarbon groups include methyl group, ethyl group, n-propyl group, n-butyl group, and tert-butyl group. From the viewpoint of further improving liquid repellency, the methyl group or ethyl group is preferred, and the methyl group is more preferred.

[0028] Z １ This is an alkylene group which may have a divalent group between carbon atoms. １ The number of carbon atoms in the alkylene group is preferably 6 or more, more preferably 7 to 100, even more preferably 10 to 48, and particularly preferably 11 to 36, from the viewpoint of improving wear resistance in the surface treatment layer. Note that the number of carbon atoms here does not include carbon atoms contained in the divalent group described later.

[0029] Z １ Divalent groups that may be included include -O-, -S-, and -C(=O)NR ５ -, -NR ５ C(=O)-, -C(=O)-, -C(=O)O-, -OC(=O)-, -NR ５ C(=O)NR ５-, -C(=O)S-, -SC(=O)-, -S(=O) ２ NR ５ -, -NR ５ S (=O) ２ -, -S (=O) ２ O-, -OS (=O) ２ -, or a phenylene group may be mentioned. However, R ５ Each of these is independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. The above divalent group has one Z １ It may contain only one, or it may contain two or more.

[0030] Z １ The group is preferably represented by the following formula (1Z): *-Z ３ - (Q ２４ -Z ４ ) ｔ２ -** ... (1Z) However, Z ３ and Z ４ Each of these is independently a linear alkylene group, Q ２４ The above Z １ It is a divalent group that may be included, t2 is 0 to 2, and * is the SiR of formula (1). １ ２ This is the bonding position on the side, and ** is Q in equation (1). １ This is the joint position on the side.

[0031] Z ３ The linear alkylene group may be any alkylene group having 1 or more carbon atoms, preferably 6 or more carbon atoms, more preferably 7 to 100 carbon atoms, even more preferably 10 to 48 carbon atoms, and particularly preferably 11 to 36 carbon atoms. ４ The linear alkylene group may be any alkylene group having 1 or more carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms. t2 is 0 to 2, preferably 0 to 1, and more preferably 0.

[0032] Z ２ This is an alkylene group that may have a single bond or a divalent group between carbon atoms. ２The number of carbon atoms in the alkylene group in the surface treatment layer is preferably 6 or more, more preferably 7 to 100, even more preferably 10 to 48, and particularly preferably 11 to 36, from the viewpoint of improving wear resistance in the surface treatment layer. Note that the carbon atoms in the divalent group are not included in the carbon number. ２ The divalent group that may be included is the Z １ Examples similar to those in [the relevant context] include [the relevant context].

[0033] Z ２ A single bond, represented by the following formula (2Z), is preferred. *-Z ５ - (Q ２５ -Z ６ ) ｔ３ -** ... (2Z) However, Z ５ and Z ６ Each of these is independently a linear alkylene group, Q ２５ The above Z ２ It is a divalent group that may be included, t3 is 0 to 2, and * is Q in equation (1). １ This is the bond position on the side, and ** is Si(R) in formula (1). ３ ) ｎ L １ ３－ｎ This is the joint position on the side.

[0034] Z ５ The linear alkylene group may be any alkylene group having 1 or more carbon atoms, preferably 6 or more carbon atoms, more preferably 7 to 100 carbon atoms, even more preferably 10 to 48 carbon atoms, and particularly preferably 12 to 36 carbon atoms. ６ The linear alkylene group may be any alkylene group having 1 or more carbon atoms, preferably 1 to 12 carbon atoms, and more preferably 1 to 6 carbon atoms. t2 is 0 to 2, preferably 0 to 1, and more preferably 0.

[0035] Z １ and Z ２ The total number of carbon atoms is preferably 6 or more, more preferably 11 to 100, even more preferably 12 to 48, and particularly preferably 20 to 36.

[0036] Q １ Q is a single bond or a (1 + q1) valence linking group. Also, q1 is an integer from 1 to 3. １Examples of linking groups in this context include (1+q1) valence groups that may have heteroatoms such as N, O, S, and Si, and may also have branching points.

[0037] Q １ If it is a single bond, then Z in equation (1) １ and Z ２ They connect directly. Also, Q １ and Z ２ If it is a single bond, then the "Z" in equation (1) １ -Q １ -Z ２ " is "Z １ " and Z １ is Si(R ３ ) ｎ L １ ３－ｎ It is directly coupled with. In these cases, q1 is 1.

[0038] Q １ If the linking group is trivalent or higher (q1 is 2 to 3), Q １ For example, a trivalent nitrogen atom (*-N(-**) ２ ), trivalent carbon atoms (*-CR ６ (-**) ２ ), tetravalent carbon atoms (*-C(-**) ３ ), trivalent silicon atom (*-SiR ７ (-**) ２ ), tetravalent silicon atom (*-Si(-**) ３ Examples include 3- to 4-valent ring structure residues, 3- to 4-valent organopolysiloxane residues, and 3- to 4-valent hydrocarbon residues, and combinations thereof. However, R ６ R is a hydrogen atom, a hydroxyl group, an alkyl group, or an alkoxy group. ７ * is an alkyl group, and * is Z １ The connection point on the side, ** is Z ２ This indicates the connection point on the side.

[0039] R ６ and R ７ Alkyl groups in and R ６The alkyl group constituting the alkoxy group in is preferably a linear or branched alkyl group having 1 to 6 carbon atoms, with linear alkyl groups being more preferred. Specific examples of alkyl groups include methyl, ethyl, n-propyl, n-butyl, and tert-butyl groups. From the viewpoint of further improving liquid repellency, methyl or ethyl groups are preferred, with methyl groups being more preferred.

[0040] Q １ The ring structure constituting the ring structure residue is preferably one selected from the group consisting of a 3- to 8-membered aliphatic ring, a benzene ring, a 3- to 8-membered heteroring, a fused ring formed by the fusion of two or three of these rings, a bridging ring with a 5- or 6-membered ring as the largest ring, and a polycyclic aggregate having two or more of these rings, where the linking group is a single bond, an alkylene group with 3 or fewer carbon atoms, an oxygen atom, or a sulfur atom. Preferred rings are a benzene ring, a 5- or 6-membered aliphatic ring, a 5- or 6-membered heteroring having a nitrogen atom or an oxygen atom, and a fused ring of a 5- or 6-membered carbon ring and a 4- to 6-membered heteroring. Specific examples of rings include the following, as well as the 1,3-cyclohexadiene ring, 1,4-cyclohexadiene ring, anthracene ring, cyclopropane ring, decahydronaphthalene ring, norbornene ring, norbornadiene ring, furan ring, pyrrole ring, thiophene ring, pyrazine ring, morpholine ring, aziridine ring, isoquinoline ring, oxazole ring, isoxazole ring, thiazole ring, imidazole ring, pyrazole ring, pyran ring, pyridazine ring, pyrimidine ring, and indene ring. Note that rings containing an oxo group (=O) are also shown below. Q １ The ring structure residues are structures in which an arbitrary hydrogen atom is missing from these ring structures.

[0041]

[0042] Q １ Examples of organopolysiloxane residues in include the following groups. However, R ａ This is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group. Also, * is Z. １ or Z ２This is the connection point.

[0043]

[0044] Q １ The base may be represented by (Q1) below. *-(Q ３１ -Z ６ ) ｋ１ -Q ３２ (-**) ｋ２ ... (Q1) However, Q ３１ It is a divalent group, Z ６ Q is a single bond or an alkylene group. ３２ This is a trivalent nitrogen atom (*-N(-**) ２ ), trivalent carbon atoms (*-CR ６ (-**) ２ ), tetravalent carbon atoms (*-C(-**) ３ ), trivalent silicon atom (*-SiR ７ (-**) ２ ), tetravalent silicon atom (*-Si(-**) ３ ), a trivalent-to-tetravalent ring structure residue, a trivalent-to-tetravalent organopolysiloxane residue, or a trivalent-to-tetravalent hydrocarbon residue, where k1 is 0 or 1 and k2 is 2 or 3.

[0045] Q ３１ The divalent group in is Z １ It is similar to a divalent group that may be included in Z. ６ The alkylene group in this product is preferably a linear alkylene group. Furthermore, the alkylene group has 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms.

[0046] Si(R) in formula (1) ３ ) ｎ L １ ３－ｎ In R ３ L is a hydrocarbon group, １ is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, and n is an integer from 0 to 2.

[0047] R ３The hydrocarbon group in is preferably an alkyl group, preferably a linear alkyl group or a branched alkyl group, and more preferably a linear alkyl group. The number of carbon atoms in the hydrocarbon group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 2.

[0048] A hydrolyzable group is a group that becomes a hydroxyl group through hydrolysis. That is, Si-L １ A hydrolyzable silyl group represented by can be converted to a silanol group represented by Si-OH through hydrolysis. The silanol groups can further react with each other to form Si-O-Si bonds. Additionally, silanol groups can undergo dehydration condensation reactions with silanol groups derived from oxides present on the surface of the substrate to form Si-O-Si bonds.

[0049] L １ Examples of hydrolyzable groups in this context include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, amino groups, and -O-N=CR groups. ｒ ２ and isocyanate groups (-NCO) are examples. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. The aryloxy group is preferably an aryloxy group having 3 to 10 carbon atoms. However, the aryl group of the aryloxy group includes heteroaryl groups. The halogen atom is preferably a chlorine atom. The acyl group is preferably an acyl group having 1 to 6 carbon atoms. The acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms. R ｒ Each of these is independently an alkyl group having 1 to 10 carbon atoms.

[0050] Groups having hydrolyzable groups include groups in which a hydrolyzable group is bonded to a linking group. Examples of linking groups include alkylene groups, -O- groups, and combinations thereof. Examples of groups having hydrolyzable groups include alkoxyalkyleneoxy groups. Preferably, an alkoxyalkyleneoxy group is a group in which an alkoxy group having 1 to 4 carbon atoms is bonded to a carbon atom of an alkyleneoxy group having 1 to 10 carbon atoms. Specific examples of alkoxyalkyleneoxy groups include 2-methoxyethoxy groups. Among them, L １From the viewpoint of ease of compound production, an alkoxy group or halogen atom having 1 to 4 carbon atoms is preferred. １ Because it exhibits less outgassing during application and superior storage stability of the compound, an alkoxy group having 1 to 4 carbon atoms is preferred, and an ethoxy group or a methoxy group is more preferred. Specific examples of hydrolyzable groups include -O-Si(OCH) ３ ) ３ ien-CH ２ -Si(OCH) ３ ) ３ , -C(CH ３ ) ２ -Si(OCH) ３ ) ３ , -O-Si(OCH ２ CH ３ ) ３ ien-CH ２ -Si(OCH) ２ CH ３ ) ３ , -C(CH ３ ) ２ -Si(OCH) ２ CH ３ ) ３ These are some examples.

[0051] n is an integer between 0 and 2, preferably 0 or 1, and more preferably 0. １ The presence of multiple layers strengthens the adhesion of the surface treatment layer to the substrate.

[0052] If n is 1 or less, there are multiple L present in one molecule. １ These may be the same or may be different from one another. From the viewpoint of the availability of raw materials and the ease of manufacturing the compound, it is preferable that the multiple Ls are the same. When n is 2, the multiple Rs present in one molecule ３ R may be the same or may be different from each other. From the viewpoint of the availability of raw materials and the ease of manufacturing the compound, multiple R ３ It is preferable that they are the same.

[0053] -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ]ｑ１ The following base is a specific example of this. However, α is an integer from 1 to 100, and * is Z. １ This is the connection point.

[0054]

[0055]

[0056] p1 is an integer greater than or equal to 0. From the viewpoint of water repellency, p1 is preferably 0 to 100, and more preferably 0 to 50. Furthermore, from the viewpoint of ease of manufacture and improved abrasion resistance, p1 is preferably 0 to 12, more preferably 0 to 6, even more preferably 0 to 4, and particularly preferably 0 to 2.

[0057] In equation (1), m1 is an integer from 1 to 4, m2 is an integer from 0 to 4, m3 is an integer from 0 to 3, and m1 + m2 is an integer from 1 to 4. In equation (1), there are m2 m3s, and m1 + m3 (if there are multiple m3s, the sum of all m3s) is an integer of 3 or greater. That is, this compound is Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ It has three or more of these. This compound has a relatively long alkyl chain Z １ -Q １ -Z ２ Because it has three or more reactive silyl groups via this compound, the surface treatment layer formed using this compound exhibits excellent water repellency and abrasion resistance.

[0058] The following compounds are specific examples of compound (1). However, β, γ, and δ are each independent integers of 1 or greater.

[0059]

[0060] [Method for producing compound (1)] The method for producing compound (1) is not particularly limited, but it can be suitably produced by the following method. That is, the method for producing compound (1) according to this embodiment includes reacting a compound represented by the following formula (1-1) with a compound represented by the following formula (1-2) to obtain compound (1-3). １１ ４－ｍ１－ｍ２ Si-[Q １１ (SiR １ ２ -O) ｐ１ H) ｍ１ {Q １１ (SiR １ ２ -O) ｐ１ -SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ -O) ｐ１ H) ｍ２ ... (1-1) X １ -SiR １ ２ -Z １２ -X ２ ... (1-2) R １１ ４－ｍ１－ｍ２ Si-[Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １２ -X ２ ] ｍ１ {Q １１ (SiR １ ２ -O) ｐ１ -SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １２ -X ２ ] ｍ２ ... (1-3) However, Z １２ Each of these is an alkylene group which may have a divalent group between carbon atoms, and Z of compound (1) １１It is a part of X. １ X is a hydroxyl group or halogen atom. ２ is a group having a carbon-carbon double bond, or X １ It is a different halogen atom, and the other signs are the same as those shown in formula (1).

[0061] Compound (1-1) can be obtained, for example, by ring-opening hexamethylcyclotrisiloxane. Compound (1-2) can be synthesized, for example, by reacting the following compounds (1-4) and (1-5). CH ２ =CH ２ -Z １３ -X ２ ... (1-4) X １ -SiR １ ２ -H …(1-5) However, Z １３ This is an alkylene group which may have a divalent group between carbon atoms, CH ２ =CH ２ -Z １３ This is Z of compound (1-2). １２ This is the relevant part, and the other symbols are as described above.

[0062] In compounds (1-3), X ２ If the group has a carbon-carbon double bond, compound (1) can be obtained by reacting it with trialkoxysilane. Also, in compounds (1-3), X ２ If it is a halogen atom, further compound (1-4) is added by a Grignard reaction, etc., Z １１ The length of the alkyl chain may be adjusted. The reaction conditions for each of the above reactions can be found in the examples described later.

[0063] [Composition] The composition of the present disclosure (hereinafter also referred to as "the composition") may contain the compound of the present disclosure, but other components are not particularly limited. Examples of components that may be included in the composition include a liquid medium, a compound having a reactive silyl group and different from compound (1), and impurities such as by-products generated in the manufacturing process of the compound of the present disclosure. If the composition contains a liquid medium, the composition may be a solution or a dispersion.

[0064] The content of compound (1) is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the total amount of the composition. In the case of the composition used in a wet coating method, the content of compound (1) is preferably 0.01 to 10% by mass, more preferably 0.02 to 5% by mass, even more preferably 0.03 to 3% by mass, and particularly preferably 0.05 to 2% by mass, based on the total amount of the composition. The liquid medium contained in the composition of this disclosure may be only one type, or it may be two or more types.

[0065] As the liquid medium, an organic solvent is preferred. Examples of organic solvents include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms. Specifically, examples include hydrocarbon organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, glycol organic solvents, and alcohol organic solvents. Among these, hydrocarbon organic solvents or ester organic solvents are preferred.

[0066] Specific examples of hydrocarbon organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexane, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene. Specific examples of ketone organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, and isophorone. Specific examples of ether organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.Specific examples of ester-based organic solvents include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, ethylene glycol monoethyl ether acetate, and ethylene glycol. Examples include monomethyl ether acetate, diethylene glycol monoethyl ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monopropyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.Specific examples of glycol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, diethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monotert-butyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, and diethylene glycol monobutyl ether. Examples include propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butylene glycol, diethylene glycol monoethyl ether, tripropylene glycol methyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and polyethylene glycol dimethyl ether.Specific examples of alcoholic organic solvents include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3-butanediol, 1,3-butanediol, 1,3-butylene glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4-methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isotridecanol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol, 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol.

[0067] Examples of organic solvents include halogenated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, siloxane compounds, and fluorine-containing organic solvents.

[0068] Specific examples of halogenated organic solvents include dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0069] Examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0070] Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0071] Examples of siloxane compounds include hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, and decamethyltetrasiloxane.

[0072] Examples of fluorine-containing organic solvents include polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); and polyfluoroaliphatic hydrocarbons (e.g., C ６ F １３ CH ２ CH ３ (For example, Asahi Clean® AC-6000 manufactured by AGC Inc.), 1,1,2,2,3,3,4-heptafluorocyclopentane (for example, Zeolora® H manufactured by Nippon Zeon Corporation); hydrofluoroether (HFE) (for example, perfluoropropyl methyl ether (C) ３ F ７ OCH ３ ) (For example, Novec® 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C ４ F ９ OCH ３ ) (For example, Novec™ 7100 manufactured by Sumitomo 3M Limited), perfluorobutyl ethyl ether (C ４ F ９ OC ２ H ５ ) (For example, Novec™ 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C ２ F ５ CF(OCH) ３ ) C ３ F ７ ) (for example, Novec™ 7300 manufactured by Sumitomo 3M Limited) and other alkyl perfluoroalkyl ethers (the perfluoroalkyl group and alkyl group may be linear or branched), and CF ３ CH ２ OCF ２ CHF ２Examples include (for example, AsahiClean® AE-3000 manufactured by AGC Inc.); and hydrofluoroolefins (HFOs) (for example, 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (for example, Amorea® AS-300 manufactured by AGC Inc.)).

[0073] The liquid medium content is preferably 60 to 99.999% by mass, more preferably 80 to 99.99% by mass, and even more preferably 90 to 99.9% by mass, based on the total amount of the composition. In the case of the composition of the disclosure used in a wet coating method, the liquid medium content is preferably 90 to 99.99% by mass, more preferably 95 to 99.98% by mass, even more preferably 97 to 99.97% by mass, and particularly preferably 98 to 99.95% by mass, based on the total amount of the composition of the disclosure.

[0074] Other compounds having a reactive silyl group include compounds that can function as surface treatment agents and are different from compound (1). Preferably, such compounds have an organo(poly)siloxane residue and a reactive silyl group, and examples include compounds represented by the following formulas (11) or (21). A ａ１ -L ａ１ -Q ａ１ - (T ａ１ ) ｍａ１ …(11) (T ａ１ ) ｍａ１ -Q ａ１ -L ａ２ -Q ａ１ - (T ａ１ ) ｍａ１ ... (21) However, A ａ１ L is a group that comprises an alkyl group or one or more selected from Si, Ge, and Sn, and does not have a reactive silyl group. ａ１ It is a divalent group, L ａ２ Q is a divalent group. ａ１ is a single bond or a (ma1+1) valence group, T ａ１ is a group containing a reactive silyl group, and ma1 is an integer greater than or equal to 1.

[0075] A ａ１The alkyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. From the viewpoint of improving liquid repellency, a linear alkyl group or a branched alkyl group is preferred. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of alkyl groups include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group. From the viewpoint of further improving liquid repellency, a methyl group, an ethyl group, or a tert-butyl group is preferred, and a methyl group is more preferred.

[0076] A ａ１ Examples of groups that include one or more selected from Si, Ge, and Sn and do not have a reactive silyl group include the groups represented by the following formulas (A1) to (A4). ａ２１ ３ M-(Q) ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２ - …(A1)

[0077] R ａ２１ ３ C-(Q ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２ - (A4) However, R ａ２１ Each of these independently comprises a hydrocarbon group, or R ｂ２１ ３ M-R ｂ２２ - and R ｂ２１ Each of these independently comprises a hydrocarbon group, or R ｃ２１ ３ M-R ｃ２２ - and R ｃ２１ Each of these independently comprises a hydrocarbon group, or R ｄ２１ ３ M-R ｄ２２ - and R ｄ２１ Each of these independently comprises a hydrocarbon group, or R ｅ２１ ３ M-R ｅ２２ - and R ｅ２１ Each of these is independently a hydrocarbon group, and R ｂ２２ , R ｃ２２ , Rｄ２２ , R ｅ２２ Each is independently an oxygen atom or an alkylene group having 1 to 6 carbon atoms, R ａ２４ Each of these independently comprises a hydrocarbon group or R ｂ２１ ３ M-R ｂ２２ - and R ａ２５ Each of these independently comprises a hydrocarbon group or R ｂ２１ ３ M-R ｂ２２ - and M is independently Si, Ge, or Sn, Q ａ１１ is -O-, -C(=O)-, or an alkylene group having 1 to 6 carbon atoms, za1 is 0 or 1, za2 is 0 or 1, R ａＳｉ This is a group represented by the following formula (RSi): -(SiR ａ４１ ２ O) ｓａ４１ -SiR ａ４１ ２ - …(RSi) R ａ４１ Each of these is independently a hydrocarbon group, and sa41 is a number greater than or equal to 0.

[0078] R ａ２１ , R ｂ２１ , R ｃ２１ , R ｄ２１ , R ｅ２１ , R ａ２４ , R ａ２５ and R ａ４１ The hydrocarbon group in this material can be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, with an aliphatic hydrocarbon group being preferred and an alkyl group being more preferred. The alkyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. From the viewpoint of improving liquid repellency, a linear alkyl group or a branched alkyl group is preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of hydrocarbon groups include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group, with a methyl group or an ethyl group being preferred, and a methyl group being more preferred, from the viewpoint of further improving liquid repellency.

[0079] R ｂ２２ , R ｃ２２ , Rｄ２２ , R ｅ２２ and Q ａ１１ In this formula, linear alkylene groups with 1 to 6 carbon atoms are preferred. Specific examples of alkylene groups with 1 to 6 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, and hexylene groups.

[0080] M is Si, Ge, or Sn, with Si being preferred. sa41 is SiR ａ４１ ２ This is the number of repeating units of O, and can be any number greater than or equal to 0, preferably 1 or more, more preferably 1 to 600, even more preferably 2 to 500, and particularly preferably 8 to 50.

[0081] From equations (A1) to (A3), (Q ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２ Specific examples of substructures excluding the above include those similar to groups (1a) to (1c) mentioned above.

[0082] L ａ１ and L ａ２ The divalent group in is preferably a chain-like group, and examples include one or more combinations selected from the groups represented by the following formulas (LA) to (LD): -(SiR ａ１１ ２ O) ｓａ１ -SiR ａ１１ ２ -...(LA) -(SiR ａ１１ ２ -R ａ１２ ) ｓａ２ -SiR ａ１１ ２ -...(LB) -(SiR ａ１１ ２ -R ａ１２ O) ｓａ３ -SiR ａ１１ ２ -...(LC) -(CR ａ１３ ２ ) ｓａ４ - ... (LD) However, R ａ１１ Each of these is independently a monovalent hydrocarbon group or organopolysiloxane residue which may have an ether bond between carbon atoms, and Rａ１２ Each of these is independently a divalent hydrocarbon group which may have an ether bond between carbon atoms, and R ａ１３ Each of these is independently a hydrogen atom or a monovalent hydrocarbon group which may have an ether bond between carbon atoms, and sa1, sa2, and sa3 are each independently a number from 1 to 200. sa4 is an integer from 1 to 200.

[0083] R ａ１１ Among these, hydrocarbon groups are preferred, and alkyl groups are more preferred. The alkyl group may be a linear alkyl group, a branched alkyl group, or a cyclic alkyl group. From the viewpoint of improving liquid repellency, linear alkyl groups or branched alkyl groups are preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. Specific examples of hydrocarbon groups include methyl groups, ethyl groups, n-propyl groups, n-butyl groups, and tert-butyl groups. From the viewpoint of further improving liquid repellency, methyl groups or ethyl groups are preferred, and methyl groups are more preferred. ａ１２ Among these, divalent hydrocarbon groups are preferred, and alkylene groups are more preferred. The alkylene group may be a linear alkylene group, a branched alkylene group, or a cyclic alkylene group. From the viewpoint of improving liquid repellency, linear alkylene groups or branched alkylene groups are preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. ａ１３ R is preferably a hydrogen atom or a monovalent hydrocarbon group, and as a monovalent hydrocarbon group, ａ１１ The structure mentioned above is preferred. ａ１３ Hydrogen atoms are more preferred. Sa1, Sa2, and Sa3 are each independently preferably 1 to 150, more preferably 1 to 100, and still more preferably 1 to 20. Sa4 is preferably 11 to 150, more preferably 21 to 100, still more preferably 23 to 80, particularly preferably 26 to 70, and most preferably 29 to 50, from the viewpoint of superior wear resistance.

[0084] L ａ１ The group is preferably represented by the following formulas (L1a) to (L1b): -Ak １-...(L1a) -Ak １ -R Ｓｉ -Ak １ - …(L1b) However, Ak １ R is a group represented by the above formula (LD), Ｓｉ This is a group represented by the above formula (LA) or the above formula (LB).

[0085] L ａ２ The group is preferably represented by the following formulas (L2a) to (L2c). -R Ｓｉ -...(L2a) -Ak １ -R Ｓｉ -Ak １ -...(L2b) -R Ｓｉ -Ak １ -R Ｓｉ - ... (L2c) However, Ak １ R is a group represented by the above formula (LD), Ｓｉ This is a group represented by the above formula (LA) or the above formula (LB).

[0086] Q ａ１ In this, the (ma1+1) valence base is preferably the base represented by the following formula (QA). * ａ２ -Q ａ４ -R ａ３ -Q ａ５ (-R ａ４ - * ａ３ ) ｍａ１ ... (QA) However, Q ａ４ R is a single bond or a divalent group. ａ３ Q is a hydrocarbon group which may have a single bond or an ether bond between carbon atoms. ａ５ R is a single bond or a (ma1+1) valence group. ａ４ is a hydrocarbon group which may have a single bond or an ether bond between carbon atoms, ma1 is an integer of 1 or more, * ａ２ is, L ａ１ or L ａ２ This is the bonding position with, * ａ３ is, T ａ１ This is the connection point.

[0087] Q ａ４ These are single bonds, -O-, -S-, -C(=O)NR ａ５ -, -NR ａ５ C(=O)-, -C(=O)-, -C(=O)O-, -OC(=O)-, -NR ａ５ C(=O)NR ａ５ -, -C(=O)S-, -SC(=O)-, -S(=O) ２ NR ａ５ -, -NR ａ５ S (=O) ２ -, -S (=O) ２ O-, -OS (=O) ２ - or a phenylene group is preferred. However, R ａ５ is a hydrogen atom or a hydrocarbon group.

[0088] Q ａ５ is a single bond, CR ａ６ ｍａ２ , NR ａ７ ｍａ３ , SiR ａ８ ｍａ４ , a (ma1+1) valent ring structure, a (ma1+1) valent organopolysiloxane residue, or a (ma1+1) valent hydrocarbon residue, R ａ６ R is a hydrogen atom, a hydroxyl group, or a hydrocarbon group which may have an ether bond between carbon atoms. ａ７ and R ａ８ m is a hydrogen atom, or a hydrocarbon group which may have an ether bond between carbon atoms, ma2 is an integer from 0 to 2, ma3 is 0 or 1, and ma4 is an integer from 0 to 2.

[0089] Q ａ１ This is *-Q in compound (1) mentioned above. １ [Z ２ -**] ｑ１ A similar structure can be cited. However, * here represents L ａ１ or L ａ２ This is the bonding position with T ａ１ This is the connection point.

[0090] T ａ１ Examples of groups include those represented by the following formula (TA). * ａ１ -[Si(R ａ１ )２ -Q ａ３ ] ｒａ１ -Si(R ａ１ ) ３ ... (TA) However, R ａ１ These are, independently, a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, Q ａ３ is an oxygen atom, or -CR ａ２ ２ - and R ａ２ is a hydrogen atom or hydrocarbon group, ra1 is an integer from 0 to 3, * ａ１ Q ａ１ This is the connection point.

[0091] A specific example when ra1 is 1 or greater is -Si(OCH ３ ) ２ -O-Si(OCH) ３ ) ３ , -Si(OCH ３ ) ２ -CH ２ -Si(OCH) ３ ) ３ , -Si(OCH ３ ) ２ -C(CH ３ ) ２ -Si(OCH) ３ ) ３ , -Si(OCH ２ CH ３ ) ２ -O-Si(OCH) ３ ) ３ , -Si(OCH ３ ) ２ -O-Si(OCH) ２ CH ３ ) ３ , -Si(OCH ２ CH ３ ) ２ -O-Si(OCH) ２ CH ３ ) ３ , -Si(OCH ２ CH ３ ) ２ -CH ２ -Si(OCH) ３ ) ３ , -Si(OCH ３ ) ２ -CH２ -Si (O) ２ HH ３ ) ３ ,-Si(OCH ２ HH ３ ) ２ -CH ２ -Si (O) ２ HH ３ ) ３ ,-Si(OCH ２ HH ３ ) ２ -C(CH ３ ) ２ -Si (O) ３ ) ３ ,-Si(OCH ３ ) ２ -C(CH ３ ) ２ -Si (O) ２ HH ３ ) ３ ,-Si(OCH ２ HH ３ ) ２ -C(CH ３ ) ２ -Si (O) ２ HH ３ ) ３ ,-Si(OH) ２ -O-Si (O) ３ ,-Si(OH) ２ -O-Si (OCH) ３ ) ３ ,-Si(OCH ３ ) ２ -O-Si (O) ３ ,-Si(OH) ２ -CH ２ -Si (O) ３ ,-Si(OH) ２ -CH ２ -Si (O) ３ ) ３ ,-Si(OCH ３ ) ２ -CH ２ -Si (O) ３ ,-Si(OH) ２ -C(CH ３ ) ２ -Si (O) ３ ,-Si(OH) ２ -C(CH３ ) ２ -Si(OCH) ３ ) ３ , -Si(OCH ３ ) ２ -C(CH ３ ) ２ -Si(OH) ３ These are some examples.

[0092] When ra1 is 0, the above group (TA) is the group represented by the following formula (Ta). * ａ１ -Si(R ａ１ ) ３ …(Ta) However, R ａ１ These are, independently, a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group, * ａ１ Q ａ１ This is the connection point.

[0093] A specific example of the above group (Ta) is the Si(R) of compound (1). ３ ) ｎ L １ ３－ｎ Similar examples include the above.

[0094] Specific examples of compound (11) and compound (21) are listed below. However, n is an integer of 0 or more, preferably 0 to 6, and more preferably 0 to 4. Also, m is an integer of 1 or more, preferably 12 to 100, and more preferably 14 to 36.

[0095]

[0096] If the composition contains compound (11) and / or compound (21), the content of compound (1) is preferably 1 to 99.9% by mass, more preferably 10 to 90% by mass, and more preferably 20 to 80% by mass, of the total 100% by mass of compound (1), compound (11), and compound (21).

[0097] The composition may further contain other components, provided that they do not impair the effects of the disclosure. Examples of other components include additives, specifically catalysts such as acid catalysts and base catalysts that promote the hydrolysis and condensation reactions of reactive silyl groups.

[0098] As catalysts, for example, any suitable acid or base, transition metals (e.g., Ti, Ni, Sn, Zr, Al, B, etc.), sulfur-containing compounds having lone pairs of electrons in their molecular structure, nitrogen-containing compounds (e.g., sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphate amide compounds, amide compounds, urea compounds), etc., can be used. Examples of acid catalysts include acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid. Examples of base catalysts include ammonia, sodium hydroxide, potassium hydroxide; and organic amines such as triethylamine and diethylamine.

[0099] Other components include metal compounds having hydrolyzable groups (hereinafter also referred to as "specific metal compounds"). When the composition of this disclosure contains a specific metal compound, the slipperiness and antifouling properties of the surface treatment layer can be further improved. Examples of specific metal compounds include metal compounds represented by any of formulas (M1) to (M3).

[0100] M(X) ｂ１ ) ｍ１１ (X ｂ２ ) ｍ１２ (X ｂ３ ) ｍ１３ …(M1) Si(X ｂ４ ) (X ｂ５ ) ３ …(M2) (X ｂ６ ) ３ Si - (Y ｂ１ )-Si(X ｂ７ ) ３ ... (M3)

[0101] In formula (M1), M is a trivalent or tetravalent metal atom, and X ｂ１ Each of these is independently a hydrolyzable group, X ｂ２ Each of these is independently a siloxane skeleton-containing group, X ｂ３Each of these is independently a hydrocarbon chain-containing group, m11 is an integer from 2 to 4, and m12 and m13 are independently integers from 0 to 2. When M is a trivalent metal atom, m11 + m12 + m13 is 3, and when M is a tetravalent metal atom, m11 + m12 + m13 is 4.

[0102] In formula (M2), X ｂ４ X is a hydrolyzable silane oligomer residue. ｂ５ Each of these is independently a hydrolyzable group or an alkyl group having 1 to 4 carbon atoms.

[0103] In formula (M3), X ｂ６ and X ｂ７ Each of these is independently a hydrolyzable group or a hydroxyl group, Y ｂ１ It is a divalent organic group.

[0104] In formula (M1), the metal represented by M also includes metalloids such as Si and Ge. M is preferably a trivalent metal or a tetravalent metal, more preferably Al, Fe, In, Hf, Si, Ti, Sn, or Zr, even more preferably Al, Si, Ti, or Zr, and particularly preferably Si.

[0105] In formula (M1), X ｂ１ The hydrolyzable group represented by is the same as the hydrolyzable group represented by L in formula (1) above, and the preferred embodiment is also the same.

[0106] X ｂ２The siloxane skeleton-containing group represented by has siloxane units (-Si-O-) and may be linear or branched. The siloxane unit is preferably a dialkylsilyloxy group, such as a dimethylsilyloxy group or a diethylsilyloxy group. The number of repeating siloxane units in the siloxane skeleton-containing group is 1 or more, preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3. The siloxane skeleton-containing group may contain a divalent hydrocarbon group in part of the siloxane skeleton. Specifically, some oxygen atoms in the siloxane skeleton may be replaced by a divalent hydrocarbon group. Examples of the divalent hydrocarbon group include alkylene groups such as methylene, ethylene, propylene, and butylene. A hydrolyzable group, a hydrocarbon group (preferably an alkyl group), etc., may be bonded to the silicon atom at the end of the siloxane skeleton-containing group. The number of elements in the siloxane skeleton-containing group is preferably 100 or less, more preferably 50 or less, and even more preferably 30 or less. The lower limit of the number of elements is preferably 10. Examples of siloxane skeleton-containing groups include *-(O-Si(CH ３ ) ２ ) ｎ CH ３ A group represented by is preferred, where n is an integer from 1 to 5, and * represents a bonding site with an adjacent atom.

[0107] X ｂ３ The hydrocarbon chain-containing group represented by may be a group consisting solely of a hydrocarbon chain, or a group having an etheric oxygen atom between carbon atoms of the hydrocarbon chain. The hydrocarbon chain may be linear or branched, with linear being preferred. The hydrocarbon chain may be saturated or unsaturated, with saturated hydrocarbon being preferred. The number of carbon atoms in the hydrocarbon chain-containing group is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. The hydrocarbon chain-containing group is preferably an alkyl group, more preferably a methyl group, an ethyl group, or a propyl group.

[0108] m1 is preferably 3 or 4.

[0109] The compound represented by formula (M1) is preferably any of the compounds represented by formulas (M1-1) to (M1-5) where M is Si, and the compound represented by formula (M1-1) is more preferred. The compound represented by formula (M1-1) is preferably tetraethoxysilane, tetramethoxysilane, or triethoxymethylsilane.

[0110] Si(X ｂ１ ) ４ …(M1-1) CH ３ -Si(X ｂ１ ) ３ ... (M1-2) C ２ H ５ -Si(X ｂ１ ) ３ ...(M1-3) n-C ３ H ７ -Si(X ｂ１ ) ３ ...(M1-4) (CH ３ ) ２ CH-Si(X ｂ１ ) ３ ... (M1-5)

[0111] In formula (M2), X ｂ４ The number of silicon atoms in the hydrolyzable silane oligomer residue represented by (C) is preferably 3 or more, more preferably 5 or more, and even more preferably 7 or more. The number of silicon atoms is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less. The hydrolyzable silane oligomer residue may have an alkoxy group bonded to a silicon atom. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, etc., with a methoxy group or an ethoxy group being preferred. The hydrolyzable silane oligomer residue may have one or more of these alkoxy groups, and it is preferable to have one. As for the hydrolyzable silane oligomer residue, (C) ２ H ５ O) ３ Si-(OSi(OC) ２ H ５ ) ２ ) ４ Examples include O-*, where * represents a bonding site with an adjacent atom.

[0112] In formula (M2), X ｂ５ Examples of hydrolyzable groups represented by the formula (1-1) above include those similar to the hydrolyzable group represented by L, a cyano group, a hydrogen atom, and an allyl group, with alkoxy groups or isocyanate groups being preferred. As for alkoxy groups, alkoxy groups having 1 to 4 carbon atoms are preferred. ｂ５ A hydrolyzable group is preferred.

[0113] Compounds represented by formula (M2) include (H ５ C ２ O) ３ -Si-(OSi(OC) ２ H ５ ) ２ ) ４ OC ２ H ５ These are some examples.

[0114] The compound represented by formula (M3) is a compound having reactive silyl groups at both ends of a divalent organic group, i.e., a bissilane. In formula (M3), X ｂ６ and X ｂ７ Examples of hydrolyzable groups represented by include alkoxy groups, acyloxy groups, ketoxime groups, alkenyloxy groups, amino groups, aminooxy groups, amide groups, isocyanate groups, and halogen atoms, with alkoxy groups or isocyanate groups being preferred. As for alkoxy groups, alkoxy groups having 1 to 4 carbon atoms are preferred, and methoxy groups or ethoxy groups are more preferred. In formula (M3), X ｂ６ and X ｂ７ These may be the same group or different groups. In terms of availability, X ｂ６ and X ｂ７ It is preferable that they are the same group.

[0115] In formula (M3), Y ｂ１ Y is a divalent organic group that links reactive silyl groups at both ends. ｂ１ The number of carbon atoms is preferably 1 to 8, and more preferably 1 to 3. ｂ１ Examples include alkylene groups, phenylene groups, and alkylene groups having an etheric oxygen atom between carbon atoms. For example, -CH２ CH ２ —, —CH ２ CH ２ CH ２ —, —CH ２ CH ２ CH ２ CH ２ —, —CH ２ CH ２ CH ２ CH ２ CH ２ —, —CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ —, —CH ２ C(CH ３ ) ２ CH ２ —, —C(CH ３ ) ２ CH ２ CH ２ C(CH ３ ) ２ —, —CH ２ CH ２ OCH ２ CH ２ —, —CH ２ CH ２ CH ２ OCH ２ CH ２ CH ２ —, —CH(CH ３ )CH ２ OCH ２ CH(CH ３ )—, and —C ６ H ４ — are included.

[0116] As the compound represented by the formula (M3), (CH ３ O) ３ Si(CH ２ ) ２ Si(OCH ３ ) ３ , (C ２ [[ID=1O8]]H ５ O) ３ Si(CH[[ID=ll3]]<o000906>) ２ Si(OC ２ H ５ ) ３(OCN) ３ Si(CH) ２ ) ２ Si (NCO) ３ , Cl ３ Si(CH) ２ ) ２ SiCl ３ , (CH ３ O) ３ Si(CH) ２ ) ６ Si(OCH) ３ ) ３ , and (C ２ H ５ O) ３ Si(CH) ２ ) ６ Si(OC) ２ H ５ ) ３ These are some examples.

[0117] The content of other components that may be included in the composition of this disclosure is preferably 10% by mass or less, and more preferably 1% by mass or less, based on the total amount of the composition of this disclosure. If the composition of this disclosure contains a specific metal compound, the content of the specific metal compound is preferably 0.01 to 30% by mass, more preferably 0.01 to 10% by mass, and even more preferably 0.05 to 5% by mass, based on the total amount of the composition of this disclosure.

[0118] The total content of the compound of this disclosure and other components (hereinafter also referred to as "solids concentration") is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the total amount of the composition of this disclosure. The solids concentration of the composition of this disclosure is a value calculated from the mass of the composition before heating and the mass after heating in a convection dryer at 120°C for 4 hours.

[0119] Since the composition disclosed herein contains a liquid medium, it is useful for coating applications and can be used as a coating solution.

[0120] [Surface Treatment Agent] In one embodiment, the surface treatment agent of the present disclosure comprises the compound of the present disclosure. Alternatively, the surface treatment agent of the present disclosure may comprise the compound of the present disclosure and a liquid medium. The surface treatment agent of the present disclosure may also be a composition of the present disclosure. A preferred embodiment of the liquid medium contained in the surface treatment agent of the present disclosure is the same as a preferred embodiment of the liquid medium contained in the composition of the present disclosure.

[0121] [Article] In one embodiment, the article of the Disclosure includes a substrate and a surface treatment layer disposed on the substrate and surface-treated with a surface treatment agent of the Disclosure.

[0122] The surface treatment layer may be formed on a part of the surface of the substrate or on the entire surface of the substrate. The surface treatment layer may be spread as a film on the surface of the substrate or may be scattered as dots. In the surface treatment layer, the compound of the present disclosure is included in a state in which hydrolysis of some or all of the reactive silyl groups has progressed and the dehydration condensation reaction of the silanol groups has progressed.

[0123] The thickness of the surface treatment layer is preferably 1 to 100 nm, and more preferably 1 to 50 nm. If the thickness of the surface treatment layer is 1 nm or more, the effects of the surface treatment are easily obtained. If the thickness of the surface treatment layer is 100 nm or less, the utilization efficiency is high. The thickness of the surface treatment layer can be calculated from the vibration period of the interference pattern obtained by the X-ray reflectivity method using an X-ray diffractometer for thin film analysis (product name "ATX-G", manufactured by RIGAKU Corporation).

[0124] The type of substrate is not particularly limited; for example, a substrate for which water repellency is required. Examples of substrates include those that may be used in contact with other articles (e.g., styluses) or human fingers; those that may be held by human fingers during operation; and those that may be placed on other articles (e.g., stands). Examples of substrate materials include metals, resins, glass, sapphires, ceramics, semiconductors, stones, fibers, nonwoven fabrics, paper, wood, furs, natural leather, artificial leather, ceramics, and composite materials thereof. Glass may be chemically strengthened.

[0125] Examples of substrates include building materials, decorative building materials, interior furnishings, transportation equipment (e.g., automobiles), signs, bulletin boards, beverage containers, tableware, aquariums, ornamental equipment (e.g., picture frames, boxes), laboratory equipment, furniture, textile products, packaging containers; glass or resin used in art, sports, games, etc.; and glass or resin used in the exterior parts (excluding display parts) of devices such as mobile phones (e.g., smartphones), personal digital assistants, game consoles, and remote controls. The substrate may be in the form of a plate or a film.

[0126] Suitable substrates include touch panel substrates, display substrates, and eyeglass lenses, with touch panel substrates being particularly preferred. Glass or transparent resin are preferred materials for the touch panel substrate.

[0127] The substrate may have one or both surfaces treated with a surface treatment such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment. A surface-treated substrate exhibits better adhesion to the surface-treated layer and improved abrasion resistance of the surface-treated layer. Therefore, it is preferable to apply the surface treatment to the surface of the substrate that comes into contact with the surface-treated layer. Furthermore, if a base layer is provided, as described later, a surface-treated substrate exhibits better adhesion to the base layer and improved abrasion resistance of the surface-treated layer. Therefore, if a base layer is provided, it is preferable to apply the surface treatment to the surface of the substrate that comes into contact with the base layer.

[0128] The surface treatment layer may be provided directly on the surface of the substrate, or a base layer may be provided between the substrate and the surface treatment layer. From the viewpoint of further improving the water repellency and abrasion resistance of the surface treatment layer, the article of the present disclosure preferably includes a substrate, a base layer disposed on the substrate, and a surface treatment layer disposed on the base layer and surface-treated with the surface treatment agent of the present disclosure.

[0129] The base layer is preferably a layer containing an oxide comprising silicon and at least one specific element selected from the group consisting of Group 1, Group 2, Group 4, Group 5, Group 13, and Group 15 elements of the periodic table.

[0130] The Group 1 elements of the periodic table (hereinafter also referred to as "Group 1 elements") refer to lithium, sodium, potassium, rubidium, and cesium. From the viewpoint of being able to form a surface treatment layer on the substrate more uniformly without defects, or from the viewpoint of further suppressing variations in the composition of the substrate between samples, lithium, sodium, and potassium are preferred as Group 1 elements, and sodium and potassium are more preferred. The substrate may contain two or more Group 1 elements.

[0131] The Group 2 elements of the periodic table (hereinafter also referred to as "Group 2 elements") refer to beryllium, magnesium, calcium, strontium, and barium. From the viewpoint of enabling the formation of a surface treatment layer on the substrate more uniformly and without defects, or of further suppressing variations in the composition of the substrate between samples, magnesium, calcium, and barium are preferred as Group 2 elements, with magnesium and calcium being more preferred. The substrate may contain two or more Group 2 elements.

[0132] The Group 4 elements of the periodic table (hereinafter also referred to as "Group 4 elements") refer to titanium, zirconium, and hafnium. From the viewpoint of forming a surface treatment layer on the substrate more uniformly and without defects, or from the viewpoint of further suppressing variations in the composition of the substrate between samples, titanium and zirconium are preferred as Group 4 elements, with titanium being more preferred. The substrate may contain two or more Group 4 elements.

[0133] The elements of Group 5 of the periodic table (hereinafter also referred to as "Group 5 elements") refer to vanadium, niobium, and tantalum. Vanadium is particularly preferred as the Group 5 element from the viewpoint of providing superior wear resistance to the surface treatment layer. The base layer may contain two or more Group 5 elements.

[0134] The elements of Group 13 of the periodic table (hereinafter also referred to as "Group 13 elements") refer to boron, aluminum, gallium, and indium. As Group 13 elements, boron, aluminum, and gallium are preferred, and boron and aluminum are more preferred, from the viewpoint of being able to form a surface treatment layer on the substrate layer more uniformly without defects, or from the viewpoint of further suppressing variations in the composition of the substrate layer between samples. The substrate layer may contain two or more Group 13 elements.

[0135] The elements of Group 15 of the periodic table (hereinafter also referred to as "Group 15 elements") refer to nitrogen, phosphorus, arsenic, antimony, and bismuth. From the viewpoint of forming a surface treatment layer on the substrate more uniformly and without defects, or from the viewpoint of further suppressing variations in the composition of the substrate between samples, phosphorus, antimony, and bismuth are preferred as Group 15 elements, and phosphorus and bismuth are more preferred. The substrate may contain two or more Group 15 elements.

[0136] The specific elements included in the base layer are preferably Group 1, Group 2, and Group 13 elements because they provide superior wear resistance to the surface treatment layer, more preferably Group 1 and Group 2 elements, and even more preferably Group 1 elements. The specific elements may consist of only one element or two or more elements.

[0137] The oxides contained in the sublayer may be a mixture of oxides of the above elements (silicon and specific elements) individually (for example, a mixture of silicon oxide and an oxide of a specific element), a composite oxide containing two or more of the above elements, or a mixture of oxides of the above elements individually and a composite oxide.

[0138] The ratio of the total molar concentration of specific elements in the substrate to the molar concentration of silicon in the substrate (specific element / silicon) is preferably 0.02 to 2.90, more preferably 0.10 to 2.00, and even more preferably 0.20 to 1.80, from the viewpoint of achieving superior wear resistance of the surface treatment layer. The molar concentration (mol%) of each element in the substrate can be measured, for example, by depth profiling analysis using X-ray photoelectron spectroscopy (XPS) with ion sputtering.

[0139] The substrate layer may be a single layer or multiple layers. The substrate layer may have irregularities on its surface. The thickness of the substrate layer is preferably 1 to 100 nm, more preferably 1 to 50 nm, and even more preferably 2 to 20 nm. If the thickness of the substrate layer is above the lower limit, the adhesion of the substrate layer to the surface treatment layer is further improved, and the abrasion resistance of the surface treatment layer is further improved. If the thickness of the substrate layer is below the upper limit, the abrasion resistance of the substrate layer itself is excellent. The thickness of the substrate layer is measured by cross-sectional observation of the substrate layer using a transmission electron microscope (TEM).

[0140] The underlayer can be formed, for example, by a vapor deposition method using a vapor deposition material, or by a wet coating method.

[0141] The vapor deposition material used in the vapor deposition method preferably contains silicon and oxides containing specific elements. Specific examples of the vapor deposition material's form include powder, molten material, sintered material, granulated material, and crushed material. From the viewpoint of ease of handling, molten material, sintered material, and granulated material are preferred. Here, molten material refers to a solid obtained by melting the vapor deposition material powder at a high temperature and then cooling and solidifying it. Sintered material refers to a solid obtained by firing the vapor deposition material powder. If necessary, a molded body may be used instead of the vapor deposition material powder by press-forming the powder. Granulated material refers to a solid obtained by kneading the vapor deposition material powder with a liquid medium (e.g., water, organic solvent) to obtain particles, and then drying the particles.

[0142] Vapor deposition materials can be manufactured by, for example, the following methods: - A method of obtaining a vapor deposition material powder by mixing silicon oxide powder and an oxide powder of a specific element. - A method of obtaining particles by kneading the vapor deposition material powder and water, and then drying the particles to obtain a vapor deposition material granule. - A method of obtaining a sintered body by drying a mixture of silicon-containing powder (e.g., silicon oxide powder, silica sand, silica gel), a powder containing a specific element (e.g., oxide powder of a specific element, carbonate, sulfate, nitrate, oxalate, hydroxide) and water, and then firing the dried mixture or a molded body formed by press molding therefrom. - A method of obtaining a molten body by melting silicon-containing powder (e.g., silicon oxide powder, silica sand, silica gel) and a powder containing a specific element (e.g., oxide powder of a specific element, carbonate, sulfate, nitrate, oxalate, hydroxide) at a high temperature, and then cooling and solidifying the molten material.

[0143] A specific example of a deposition method using deposition materials is the vacuum deposition method. The vacuum deposition method is a method in which the deposition material is evaporated in a vacuum chamber and deposited onto the surface of a substrate. The deposition temperature (for example, the temperature of the boat in which the deposition material is placed when using a vacuum deposition apparatus) is preferably 100 to 3,000°C, and more preferably 500 to 3,000°C. The deposition pressure (for example, the pressure in the chamber in which the deposition material is placed when using a vacuum deposition apparatus) is preferably 1 Pa or less, and more preferably 0.1 Pa or less. When forming a base layer using a deposition material, one deposition material may be used, or two or more deposition materials containing different elements may be used.

[0144] Specific examples of evaporation methods for deposition materials include the resistance heating method, in which the deposition material is melted and evaporated on a high-melting-point metal resistance heating boat, and the electron gun method, in which an electron beam is irradiated onto the deposition material to directly heat it, melt the surface, and evaporate it. The electron gun method is preferred as an evaporation method for deposition materials because it allows for localized heating, enabling the evaporation of high-melting-point substances, and because areas not exposed to the electron beam remain at low temperatures, eliminating the risk of reaction with the container or contamination by impurities. Multiple boats may be used for evaporation, or all deposition materials may be placed in a single boat. The deposition method may be co-deposition or alternating deposition. Specifically, examples include mixing silica and a specific element source in the same boat, co-deposition using silica and a specific element source in separate boats, and alternating deposition using separate boats. The deposition conditions and order are appropriately selected depending on the composition of the underlying layer.

[0145] In the wet coating method, it is preferable to form a base layer on the substrate by a wet coating method using a coating solution containing a silicon-containing compound, a compound containing a specific element, and a liquid medium.

[0146] Specific examples of silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partial hydrolysis condensates of alkoxysilanes.

[0147] Specific examples of compounds containing specific elements include oxides of specific elements, alkoxides of specific elements, carbonates of specific elements, sulfates of specific elements, nitrates of specific elements, oxalates of specific elements, and hydroxides of specific elements.

[0148] Examples of liquid media include those similar to the liquid media contained in the composition of this disclosure.

[0149] The liquid medium content is preferably 0.01 to 20% by mass, and more preferably 0.1 to 10% by mass, relative to the total amount of coating liquid used to form the base layer.

[0150] Specific examples of wet coating methods for forming a base layer include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet coating, flow coating, roll coating, casting, Langmuir-Bludget coating, and gravure coating.

[0151] It is preferable to wet coat the coating liquid and then dry the coating film. The drying temperature of the coating film is preferably 20 to 200°C, and more preferably 80 to 160°C.

[0152] The articles of this disclosure may be optical materials having a surface treatment layer as the outermost layer. Preferred optical materials include a wide variety of optical materials, in addition to optical materials related to displays. Examples of optical materials include displays such as cathode ray tubes (CRTs; e.g., personal computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin-film EL dot matrix displays, rear projection displays, fluorescent display tubes (VFDs), and field emission displays (FEDs), or protective plates for such displays, or materials with an anti-reflective coating applied to their surfaces.

[0153] The articles of this disclosure are preferably optical components. Examples of optical components 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 equipment such as endoscopes, photocopiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and anti-reflective films. Other examples of optical components include front protective plates, anti-reflective plates, polarizing plates, and anti-glare plates for displays such as PDPs and LCDs; disc surfaces for optical discs such as Blu-ray (registered trademark) discs, DVD discs, CD-Rs, and MOs; optical fibers; and display surfaces for watches. In particular, the articles of this disclosure are preferably displays or touch panels.

[0154] The articles disclosed herein may be medical devices or medical materials. The articles disclosed herein may also be automotive interior and exterior components. Examples of exterior components include windows, light covers, and aftermarket camera covers. Examples of interior components include instrument panel covers, navigation system touch panels, and decorative interior components.

[0155] When the article of this disclosure is an optical component, the material constituting the surface of the substrate is an optical component material, such as glass or transparent plastic. Furthermore, when the article of this disclosure is an optical component, a functional layer such as a hard coat layer or an anti-reflective layer may be formed on the surface (outermost layer) of the substrate. The anti-reflective layer may be either a single-layer anti-reflective layer or a multi-layer anti-reflective layer. Examples of inorganic materials that can be used for the anti-reflective layer include SiO ２ SiO, ZrO ２ , TiO ２ ,TiO,Ti ２ O ３ Ti ２ O ５ Al ２ O ３ Ta ２ O ５ Ta ３ O ５Nb ２ O ５ , HfO ２ Si ３ N ４ , CEO ２ , MgO, Y ２ O ３ , SnO ２ MgF ２ , and WO ３ These are examples. These inorganic materials may be used individually or in combination of two or more (for example, as a mixture). When a multilayer anti-reflective layer is used, the outermost layer is SiO ２ It is preferable to use and / or SiO. If the article of this disclosure is an optical glass component for a touch panel, it may have a thin film made of a transparent electrode, such as indium tin oxide (ITO) or indium zinc oxide, on a part of the surface of the substrate (glass). The substrate may also have an insulating layer, an adhesive layer, a protective layer, a decorative frame layer (I-CON), an atomizing film layer, a hard coating film layer, a polarizing film, a phase difference film, and a liquid crystal display module, depending on its specific specifications.

[0156] [Method for Manufacturing Articles] The method for manufacturing articles according to this disclosure is, for example, a method of manufacturing an article in which a surface treatment layer is formed on a substrate by performing a surface treatment on a substrate using the surface treatment agent of this disclosure. Examples of surface treatments include dry coating and wet coating methods.

[0157] Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferred as a dry coating method from the viewpoint of suppressing compound decomposition and the simplicity of the equipment. During vacuum deposition, pellet-like material may be used, in which a porous metal such as iron or steel is impregnated with the compound of this disclosure. Alternatively, a composition containing the compound of this disclosure and a liquid medium may be impregnated into a porous metal such as iron or steel, and the liquid medium may be dried to produce a pellet-like material impregnated with the compound of this disclosure. When using pellet-like material, compounds that are solid at 25°C have lower molecular mobility, thus suppressing deterioration of storage stability due to hydrolysis and condensation reactions.

[0158] Examples of the wet coating method include a spin coating method, a wipe coating method, a spray coating method, a squeegee coating method, a dip coating method, a die coating method, an inkjet method, a flow coating method, a roll coating method, a casting method, a Langmuir-Blodgett method, and a gravure coating method.

[0159] In order to improve the wear resistance of the surface treatment layer, an operation for promoting the reaction between the compound of the present disclosure and the substrate may be performed as necessary. Examples of such an operation include heating, humidifying, light irradiation, etc. For example, by heating a substrate having a surface treatment layer formed in an atmosphere containing moisture, hydrolysis reactions of hydrolyzable groups, reactions between hydroxyl groups on the surface of the substrate and silanol groups, and formation of siloxane bonds by condensation reactions of silanol groups can be promoted. After the surface treatment, a compound in the surface treatment layer that is not chemically bonded to other compounds or the substrate may be removed as necessary. Examples of the removal method include a method of pouring a solvent over the surface treatment layer and a method of wiping with a cloth impregnated with a solvent.

[0160] (Another embodiment) In the above formula (1), a compound in which m1 + m3 is 2, that is, a compound having two Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ｑ１ also has good wear resistance. In particular, when used in combination with the compound (11) and / or the compound (21), preferably the compound (11), it becomes a surface treatment agent capable of forming a surface treatment layer excellent in water repellency and wear resistance. That is, the composition according to another embodiment is a composition containing the following compound (2) and the compound (11) and / or the compound (21). R １１ ４－ｍ１－ｍ２ Si-[Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １ -Q １ [Z ２ -Si(R３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ１ {Q １１ (SiR １ ２ -O) ｐ１ -SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ -O) ｐ１ -SiR １ ２ -Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ３} ｍ２ ... (2) However, R １１ Each of these is independently a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue, Q １１ Each is independently an oxygen atom or a hydrocarbon group, and R １ Each of these is independently a hydrocarbon group, Z １ Each of these is an alkylene group which may have a divalent group between carbon atoms, Q １ Z is a single bond or a (1+q1) valence linking group. ２ Each of these is an alkylene group which may have a single bond or a divalent group between carbon atoms, R ３ Each of these is independently a hydrocarbon group, L １ Each of the following is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; each of the following is independently an integer from 0 to 2; each of the following is independently an integer of 0 or more; each of the following is independently an integer from 1 to 3; m1 is 1 or 2; m2 is an integer from 0 to 4; m3 is an integer from 0 to 2; and m1 + m3 (if there are multiple m3s, the sum of all m3s) is 2.

[0161] The symbols in formula (2) are the same as those in formula (1), and the preferred embodiments are also the same. Furthermore, the components such as the liquid medium that may be included in this composition are as described above, so their explanation is omitted here.

[0162] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. Examples 1 to 3 are examples, examples 4 to 5 are comparative examples, and examples 6 to 12 are reference examples.

[0163] [Synthesis of Compound I-1] 10 g of 18-bromo-1-octadecene was mixed with 10 g of dichloromethane, 10 g of chlorodimethylsilane, and a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 50 mg), and the mixture was stirred at 25°C for 24 hours. After removing the low-boiling components under reduced pressure, 10 g of dichloromethane, 10 g of triethylamine, and 10 g of water were added, and the mixture was stirred at 25°C for 1 hour. 2 M hydrochloric acid and dichloromethane were added, and after extraction, the low-boiling components were removed under reduced pressure. Finally, 5.8 g of Compound I-1 was obtained by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate).

[0164]

[0165] [Synthesis of Compound I-2] Compound I-1 (4.0 g) was dissolved in THF (10 g). After cooling to 0°C, 5 ml of 1.6 mol / L n-butyllithium-hexane solution was added and the mixture was stirred for 10 minutes. Then, hexamethylcyclotrisiloxane (2.1 g) was added and the mixture was stirred at 0°C for 24 hours. Then, trichloro(methyl)silane (0.45 g) was added and the mixture was stirred at 20°C for 2 hours. After extraction with hydrochloric acid and decane, low-boiling point components were removed by vacuum distillation, and 2.5 g of compound I-2 was obtained by flash column chromatography using silica gel (developing solvent: decane / dichloromethane). The average value of n1 + n2 + n3 from NMR was 9.

[0166]

[0167] 1 ​H-NMR (400 MHz, CDCl3) δ 3.42 (t, J = 4.4 Hz, 6H), 1.87 - 1.04 (m, 96H), 0.69 (t, J = 8.1 Hz, 6H), 0.39 - -0.24 (m, 75H).

[0168] [Synthesis of Compound I-3] 11-bromo-1-undecene (6.0 g) was mixed with THF (20 g) and magnesium (1.1 g) and stirred at 60°C for 2 hours. After removing the magnesium residue by filtration of the reaction mixture, the reaction mixture was cooled to 0°C, and compound I-2 (2.0 g) and copper(II) chloride (0.01 g) were added and stirred at 0°C for 24 hours. Hydrochloric acid and decane were added for extraction, and low-boiling point components were removed by reduced-pressure distillation. Finally, 1.3 g of compound I-3 was obtained by flash column chromatography using silica gel (developing solvent: decane). The average value of n1 + n2 + n3 from NMR was 9.

[0169]

[0170] 1 H-NMR (400 MHz, CDCl3) δ 5.90-5.65 (m, 3H), 5.23 - 4.74 (m, 6H), 2.10-2.00 (m, 6H), 1.60 - 1.10 (m, 150H), 0.82 - 0.55 (m, 6H), 0.39 - -0.24 (m, 75H).

[0171] [Synthesis of Compound I-4] Compound I-3 (1.0 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (2.5 g) were added, and the mixture was stirred at 50°C for 2 hours. By distilling off the low-boiling components under reduced pressure, 1.1 g of compound I-4 was obtained.

[0172]

[0173] 1 ​​H-NMR (400 MHz, CDCl3) δ 3.70-3.40 (m, 27H), 1.66 - 1.08 (m, 162H), 0.82 - 0.55 (m, 12H), 0.39 - -0.24 (m, 75H).

[0174] [Synthesis of Compound II-1] Compound I-1 (4.0 g) was dissolved in THF (10 g). After cooling to 0°C, 5 ml of 1.6 mol / L n-butyllithium-hexane solution was added and the mixture was stirred for 10 minutes. Then, hexamethylcyclotrisiloxane (2.1 g) was added and the mixture was stirred at 0°C for 24 hours. Then, tetrachlorosilane (0.51 g) was added and the mixture was stirred at 20°C for 2 hours. After extraction with hydrochloric acid and decane, the low-boiling point components were removed by vacuum distillation, and 2.2 g of Compound II-1 was obtained by flash column chromatography using silica gel (developing solvent: decane / dichloromethane). The average value of n1 + n2 + n3 + n4 from NMR was 12.

[0175]

[0176] 1 H-NMR (400 MHz, CDCl3) δ 3.62-3.44 (m, 8H), 1.87 - 1.04 (m, 128H), 0.82 - 0.55 (m, 8H), 0.39 - -0.24 (m, 96H).

[0177] [Synthesis of Compound II-2] 8.0 g of 11-bromo-1-undecene was mixed with 20 g of THF and 1.1 g of magnesium, and the mixture was stirred at 60°C for 2 hours. After filtering the reaction mixture to remove the magnesium residue, the mixture was cooled to 0°C, and 2.0 g of Compound II-1 and 0.01 g of copper(II) chloride were added. The mixture was stirred at 0°C for 24 hours. Hydrochloric acid and decane were added for extraction, and low-boiling point components were removed by reduced-pressure distillation. Finally, 0.9 g of Compound II-2 was obtained by flash column chromatography using silica gel (developing solvent: decane). The average value of n1 + n2 + n3 + n4 from NMR was 12.

[0178]

[0179] 1 ​​H-NMR (400 MHz, CDCl3) δ 5.90-5.65 (m, 4H), 5.23 - 4.74 (m, 8H), 2.10-2.00 (m, 8H), 1.60 - 1.10 (m, 200H), 0.82 - 0.55 (m, 8H), 0.39 - -0.24 (m, 96H).

[0180] [Synthesis of Compound II-3] Compound II-2 (0.9 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (2.5 g) were added, and the mixture was stirred at 50°C for 2 hours. By distilling off the low-boiling components under reduced pressure, 1.0 g of Compound II-3 was obtained.

[0181]

[0182] 1 H-NMR (400 MHz, CDCl3) δ 3.70-3.40 (m, 36H), 1.66 - 1.08 (m, 216H), 0.82 - 0.55 (m, 16H), 0.39 - -0.24 (m, 96H).

[0183] [Synthesis of Compound III-1] 65 g of hexamethylcyclotrisiloxane was mixed with 101 g of THF (tetrahydrofuran) and stirred at 25°C until dissolved. The reaction mixture was then cooled to -30°C, and 100 mL of methyllithium (3.1 M in diethoxymethane) was added. The mixture was stirred at -30°C for 2 hours. Next, 100 g of chlorodimethylsilane was added and stirred at -30°C for 1 hour. The mixture was then raised to 25°C and stirred for another hour. After removing the low-boiling components by distillation, hexane and water were added for extraction, and the mixture was purified by distillation to obtain 65 g of Compound III-1.

[0184]

[0185] 1 H NMR (400 MHz, CDCl3) δ 4.71 (p, J = 2.8 Hz, 1H), 0.50 - -0.23 (m, 27H).​​

[0186] [Synthesis of Compound III-2] Compound III-1 (1.0 g) was mixed with dichloromethane (20 g) and 18-bromo-1-octadecene (1.0 g) and stirred at 25°C until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added and stirred at 25°C for 2 hours. After removing the low-boiling components under reduced pressure, 1.5 g of Compound III-2 was obtained by flash column chromatography using silica gel (developing solvent: decane / dichloromethane).

[0187]

[0188] 1 H NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.94 - 1.78 (m, 2H), 1.52 - 1.10 (m, 30H), 0.53 (t, J = 7.7 Hz, 2H), 0.39 - -0.24 (m, 27H).

[0189] [Synthesis of Compound III-3] 11-bromo-1-undecene (2.0 g) was mixed with THF (20 g) and magnesium (1.1 g) and stirred at 60°C for 2 hours. After removing the magnesium residue by filtration of the reaction mixture, the reaction mixture was cooled to 0°C, and Compound III-2 (1.5 g) and tetrachlorocopper(II) dilithium solution (0.1 M in THF, 0.05 g) were added and stirred at 0°C for 24 hours. After extraction with hydrochloric acid and decane, low-boiling point components were removed by vacuum distillation, and 1.1 g of Compound III-3 was obtained by flash column chromatography using silica gel (developing solvent: decane).

[0190]

[0191] 1 ​​H NMR (400 MHz, CDCl3) δ 6.00 - 5.67 (m, 1H), 5.15 - 4.67 (m, 2H), 2.19 - 1.86 (m, 2H), 1.55 - 1.08 (m, 50H), 0.53 (dd, J = 10.0, 5.3 Hz, 2H), 0.39 - -0.24 (m, 27H).

[0192] [Synthesis of Compound III-4] Compound III-3 (1.1 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. By removing the solvent under reduced pressure, 1.3 g of Compound III-4 was obtained.

[0193]

[0194] 1 H NMR (400 MHz, CDCl3) δ 3.48 (s, 9H), 1.50 - 1.01 (m, 54H), 0.63 - 0.51 (m, 2H), 0.44 (t, J = 7.7 Hz, 2H), 0.39 - -0.24 (m, 27H).

[0195] [Preparation of Composition III] Composition III was prepared by mixing compound I-4 (0.2 g) and compound III-4 (0.8 g) until homogeneous.

[0196] [Synthesis of Compound IV-1] Compound (IV-1) was obtained according to the method described in International Publication No. 2021 / 187184. The average number of repeating units n was 17.

[0197]

[0198] ​[Synthesis of Compound V-1] Hexamethylcyclotrisiloxane (10 g) was dissolved in THF (10 g). 1,8-Diazabicyclo[5.4.0]-7-Undecene (0.1 g) and water (0.1 g) were added, and the mixture was stirred at 25°C for 24 hours. Then, chlorotrimethoxysilane (2.5 g) and triethylamine (5.5 g) were added, and the mixture was stirred at 20°C for 2 hours. After extraction with hydrochloric acid and decane, low-boiling components were removed by vacuum distillation, and 4.2 g of the following compound was obtained by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate). The average value of n from NMR was 42.

[0199]

[0200] 1 H-NMR (400 MHz, CDCl3) δ 3.70-3.40 (m, 18H), 0.21 - -0.21 (m, 252H).

[0201] [Manufacturing of Articles] In a polypropylene container equipped with a stirrer and thermometer, 0.5% by mass of the above compound or composition and 2% by mass of dibutyltin dilaurate were added to 97.5% by mass of heptane and stirred at 25°C for 30 minutes to obtain a surface treatment agent. A glass substrate (water contact angle: 5 degrees, 100 mm x 100 mm) whose surface was cleaned by plasma treatment was used as the substrate. The surface treatment agent was applied to the surface of the glass substrate by spray coating and heat-treated at 140°C for 30 minutes. At this time, the amount of surface treatment agent applied relative to the surface area of ​​the glass substrate was 0.074 mL / cm². ２ The amount of surface treatment agent applied was adjusted accordingly. Then, it was kept in a constant temperature and humidity chamber set to 140°C for one hour. The surface of the coating formed by the application of the surface treatment agent was wiped with a paper cloth soaked in ethanol to obtain the finished product.

[0202] ​[Evaluation] <Water Contact Angle> Approximately 2 μL of distilled water was dropped onto the surface treatment layer of each example's article, and the initial water contact angle (°) was measured using a contact angle measuring device (product name "DM-500", manufactured by Kyowa Interface Science Co., Ltd.). The average value measured at five locations on the surface treatment layer was defined as the water contact angle. The 2θ method was used to calculate the water contact angle. A larger initial water contact angle indicates better water repellency of the surface treatment layer. The measurement results of the initial water contact angle are shown in each table. (Evaluation Criteria) A (Excellent): Initial water contact angle greater than 112 degrees B (Good): Initial water contact angle greater than 107 degrees and 112 degrees or less C (Poor): Initial water contact angle 107 degrees or less

[0203] <Abrasion Resistance Test> Using a reciprocating traverse testing machine (KNT Co., Ltd., custom-made), a flannel cloth conforming to JIS L0803 was used to test the surface of surface-treated glass at a rate of 3N / 4cm². ２ After applying a load and undergoing 100 reciprocating wear cycles at a speed of 40 cycles per minute, the water contact angle was evaluated using the method described above. (Evaluation criteria) A (Excellent): Contact angle after wear is greater than 110 degrees B (Good): Contact angle after wear is greater than 105 degrees and less than or equal to 110 degrees C (Poor): Contact angle after wear is 105 degrees or less

[0204]

[0205] As shown in the results above, in equation (1), Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ Articles of Examples 1 to 3, which have a surface treatment layer using a compound having three or more of the structure represented by [ ], were found to have a higher water contact angle and superior abrasion resistance compared to articles of Examples 4 to 5.

[0206] <Examples of other embodiments> The following are examples using compound (2).

[0207] [Synthesis of Compound VI-1] 3.0 g of 1,1,3,3,5,5,7,7-Octamethyltetrasiloxane was mixed with 20 g of dichloromethane and 4.0 g of 18-bromo-1-octadecene and stirred at 25°C until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added and stirred at 25°C for 2 hours. After removing the low-boiling components under reduced pressure, 3.2 g of Compound VI-1 was obtained by flash column chromatography using silica gel (developing solvent: decane / dichloromethane).

[0208]

[0209] 1 H NMR (400 MHz, CDCl3) δ 3.42 (t, J = 4.7 Hz, 4H), 1.82 - 1.12 (m, 64H), 0.71 (t, J = 8.3 Hz, 4H), 0.39 - -0.24 (m, 24H).

[0210] [Synthesis of Compound VI-2] 11-bromo-1-undecene (4.0 g) was mixed with THF (20 g) and magnesium (1.1 g) and stirred at 60°C for 2 hours. After removing the magnesium residue by filtration of the reaction mixture, the reaction mixture was cooled to 0°C, and Compound VI-1 (1.5 g), nickel(II) chloride (0.01 g), and 1,3-butadiene (approximately 15% toluene solution) (2.0 g) were added and stirred at 0°C for 24 hours. After extraction with hydrochloric acid and decane, low-boiling point components were removed by vacuum distillation, and 1.1 g of Compound VI-2 was obtained by flash column chromatography using silica gel (developing solvent: decane).

[0211]

[0212] 1 ​​H NMR (400 MHz, CDCl3) δ 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 2H), 5.19 - 4.77 (m, 4H), 2.16 - 1.82 (m, 4H), 1.60 - 1.10 (m, 100H), 0.71 (t, J = 8.3 Hz, 4H),0.39 - -0.24 (m, 24H).

[0213] [Synthesis of Compound VI-3] Compound VI-2 (1.0 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (3.6 g) were added, and the mixture was stirred at 50°C for 2 hours. By distilling off the low-boiling components under reduced pressure, 1.15 g of compound VI-3 was obtained.

[0214]

[0215] 1 H NMR (400 MHz, CDCl3) δ 3.58 (s, 18H), 1.59 - 1.15 (m, 108H), 0.84 - 0.47 (m, 8H), 0.39 - -0.24 (m, 24H).

[0216] [Synthesis of Compound VII-1] 10 g of 18-bromo-1-octadecene was mixed with 10 g of dichloromethane, 3 g of 1,1,1,3,5,7,7,7-octamethyltetrasiloxane, and a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 50 mg), and the mixture was stirred at 25°C for 24 hours. After removing the low-boiling components under reduced pressure, 6.8 g of Compound VII-1 was obtained by flash column chromatography using silica gel (developing solvent: hexane / dichloromethane).

[0217]

[0218] 1 ​​H-NMR (400 MHz, CDCl3) δ 3.42 (t, J = 4.7 Hz, 4H), 1.87 - 1.04 (m, 64H), 0.69 (t, J = 8.2 Hz, 4H), 0.39 - -0.24 (m, 24H).

[0219] [Synthesis of Compound VII-2] 11-bromo-1-undecene (4.0 g) was mixed with THF (20 g) and magnesium (1.1 g) and stirred at 60°C for 2 hours. After removing the magnesium residue by filtration of the reaction mixture, the reaction mixture was cooled to 0°C, and Compound VII-1 (1.5 g) and copper(II) chloride (0.01 g) were added and stirred at 0°C for 24 hours. Hydrochloric acid and decane were added for extraction, and low-boiling point components were removed by reduced-pressure distillation. Finally, 1.0 g of Compound VII-2 was obtained by flash column chromatography using silica gel (developing solvent: decane).

[0220]

[0221] 1 H-NMR (400 MHz, CDCl3) δ 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 2H), 5.23 - 4.74 (m, 4H), 2.03 (tdt, J = 7.8, 6.8, 1.1 Hz, 4H), 1.60 - 1.10 (m, 100H), 0.69 (t, J = 8.2 Hz, 4H), 0.39 - -0.24 (m, 24H).

[0222] [Synthesis of Compound VII-3] Compound VII-2 (1.0 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (2.5 g) were added, and the mixture was stirred at 50°C for 2 hours. By distilling off the low-boiling point components under reduced pressure, 1.20 g of compound VII-3 was obtained.

[0223]

[0224] 1 ​​H-NMR (400 MHz, CDCl3) δ 3.58 (s, 18H), 1.66 - 1.08 (m, 108H), 0.82 - 0.55 (m, 8H), 0.39 - -0.24 (m, 24H).

[0225] [Synthesis of Compound VIII-1] 1,1,1,3,5,5,5-Heptamethyltrisiloxane (10 g) was mixed with dichloromethane (100 g) and trichloroisocyanuric acid (14 g) and stirred at 25°C for 3 hours. The reaction mixture was then filtered to remove insoluble matter, and the low-boiling components were removed by distillation of the filtrate. Water (20 g), THF (40 g), and triethylamine (10 g) were added to the obtained crude solution and stirred at 25°C for 2 hours. Hexane and water were added for extraction, and the low-boiling components were removed by distillation. The obtained crude solution was purified by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate) to obtain 8.3 g of Compound VIII-1. The structure of Compound VIII-1 was confirmed from the following NMR data.

[0226]

[0227] 1 H-NMR (400 MHz, CDCl3) δ: 2.41 (q, J = 7.2 Hz, 1H), 0.20 - 0.21 (m, 21H).

[0228] [Synthesis of Compound VIII-2] Compound VIII-1 (2.0 g) was mixed with THF (10 g), cooled to 0°C, and then lithium bis(trimethylsilyl)amide (1 M in THF) (1.3 mL) was added and the mixture was stirred at 0°C for 10 minutes. Next, a solution of hexamethylcyclotrisiloxane (5.6 g) dissolved in THF (5.6 g) was added and the mixture was stirred at 0°C for 24 hours. Then hydrochloric acid (2 M) (20 mL) was added and the mixture was stirred at 0°C for 10 minutes. After extraction with hexane and water, the low-boiling point components were removed by distillation. The resulting composition was purified by flash column chromatography using silica gel (developing solvent: decane / butyl butyrate) to obtain 3.7 g of Compound VIII-2.

[0229] ​

[0230] [Synthesis of Compound VIII-3] 5 g of 18-bromo-1-octadecene was mixed with a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 3 mg) and chlorodimethylsilane (1.3 g) to obtain 5.5 g of Compound VIII-3.

[0231]

[0232] [Synthesis of Compound VIII-4] Compound VIII-2 (2.3 g) was mixed with dichloromethane (20 g), compound VIII-3 (0.75 g), and triethylamine (1 g), and stirred at 25°C for 2 hours. After extraction with hexane and water, the low-boiling point components were removed by reduced-pressure distillation, and then 1.8 g of compound VIII-4 was obtained by flash column chromatography using silica gel (developing solvent: decane / butyl butyrate). The average value of n in compound VIII-4 was 9. The structure of compound VIII-4 was confirmed from the following NMR data.

[0233]

[0234] 1 H-NMR (400 MHz, CDCl3) δ: 3.33 (t, J = 6.9 Hz, 2H), 1.78 (dt, J = 14.5, 7.0 Hz, 2H), 1.42 - 1.08 (m, 30H), 0.45 (t, J = 7.7 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0235] [Synthesis of Compound VIII-5] Compound VIII-4 (1.8 g) was mixed with THF (20 g) and allyl magnesium chloride solution (2.0 M in THF) (20 mL) and stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling components were removed by reduced-pressure distillation. Then, 1.5 g of compound VIII-5 was obtained by flash column chromatography using silica gel (developing solvent: decane / butyl butyrate). The average value of n in compound VIII-5 was 9. The structure of compound VIII-5 was confirmed from the following NMR data.

[0236] ​

[0237] 1 H-NMR (400 MHz, CDCl3) δ: 5.74 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.01 - 4.76 (m, 2H), 2.07 - 1.87 (m, 2H), 1.41 - 0.97 (m, 34H), 0.45 (dd, J = 9.5, 5.9 Hz, 2H), 0.09 - 0.12 (m, 81H).

[0238] [Synthesis of Compound VIII-6] Compound VIII-5 (1.5 g) was dissolved in dichloromethane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.60 g) were added, and the mixture was stirred at 50°C for 2 hours. By removing the solvent under reduced pressure, 1.6 g of compound 3-65 was obtained. The average value of n in compound VIII-6 was 9. The structure of compound VIII-6 was confirmed from the following NMR data.

[0239]

[0240] 1 H-NMR (400 MHz, CDCl3) δ: 3.49 (s, 9H), 1.81 - 0.97 (m, 38H), 0.65 - 0.51 (m, 2H), 0.45 (dd, J = 9.8, 5.3 Hz, 2H) , 0.09 - 0.12 (m, 81H).

[0241] [Preparation of Composition IX] Composition IX was prepared by mixing compound VII-3 (0.2 g) and compound III-4 (0.8 g) until homogeneous.

[0242] [Preparation of Composition X] Composition X was prepared by mixing compound VII-3 (0.2 g) and compound VIII-6 (0.8 g) until homogeneous.

[0243] ​​[Synthesis of Composition XI] 11-bromo-1-undecene (2.0 g) was mixed with THF (20 g) and magnesium (1.1 g) and stirred at 60°C for 2 hours. After removing the magnesium residue by filtration of the reaction mixture, compound III-2 (1.5 g) and copper(II) chloride (0.01 g) were added and stirred at 60°C for 2 hours. Hydrochloric acid and decane were added for extraction, and the low-boiling point components were removed by distillation under reduced pressure. Then, flash column chromatography using silica gel (developing solvent: decane) was performed to obtain 0.55 g of Composition XI, in which compound III-3, compound XI-1, compound XI-2, and compound XI-3 were in a mol ratio of 71 / 20 / 6 / 3.

[0244]

[0245] 1 H NMR (400 MHz, CDCl3) δ 6.00 - 5.67 (m, 1H), 5.15 - 4.67 (m, 2H), 2.19 - 1.86 (m, 2H), 1.55 - 1.08 (m, 50H), 0.53 (dd, J = 10.0, 5.3 Hz, 2H), 0.39 - -0.24 (m, 27H).

[0246]

[0247] 1 H NMR (400 MHz, CDCl3) δ 1.48 - 1.11 (m, 32H), 0.96 - 0.60 (m, 5H), 0.39 - -0.24 (m, 27H).

[0248]

[0249] 1 H NMR (400 MHz, CDCl3) δ 6.00 - 5.67 (m, 1H), 5.15 - 4.67 (m, 2H), 2.19 - 1.86 (m, 2H), 1.55 - 1.08 (m, 28H), 0.85 - 0.60 (m, 2H), 0.39 - -0.24 (m, 27H).

[0250]

[0251] ​​​​1 H NMR (400 MHz, CDCl3) δ 1.49 - 1.03 (m, 68H), 0.71 (t, J = 8.3 Hz, 4H), 0.39 - -0.24 (m, 54H).

[0252] [Synthesis of Composition XII] Composition XI (0.5 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (2.5 g) were added, and the mixture was stirred at 50°C for 2 hours. By distilling off the low-boiling components under reduced pressure, 0.6 g of Composition XII was obtained, with compounds III-4, XI-1, XII-1, and XI-3 in a mol ratio of 71 / 20 / 6 / 3.

[0253]

[0254] 1 H NMR NMR (400 MHz, CDCl3) δ 3.48 (s, 9H), 1.50 - 1.01 (m, 32H), 0.63 - 0.31 (m, 4H), 0.39 - -0.24 (m, 27H)

[0255] [Synthesis of Compound XIII-1] 3.0 g of 1,1,3,3,5,5,7,7,9,9,11,11,13,13,15,15-Hexadecamethyloctasiloxane was added to 20 g of dichloromethane and 3.0 g of 18-bromo-1-octadecene, and the mixture was stirred at 25°C until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added, and the mixture was stirred at 25°C for 2 hours. After removing the low-boiling components under reduced pressure, 3.5 g of Compound XIII-1 was obtained by flash column chromatography using silica gel (developing solvent: decane / dichloromethane).

[0256]

[0257] 1 ​​H-NMR (400 MHz, CDCl3) δ 3.56-3.21 (m, 4H), 1.87 - 1.04 (m, 64H), 0.82-0.42 (m, 4H), 0.39 - -0.24 (m, 48H).

[0258] [Synthesis of Compound XIII-2] 11-bromo-1-undecene (4.0 g) was mixed with THF (20 g) and magnesium (1.1 g) and stirred at 60°C for 2 hours. After removing the magnesium residue by filtration of the reaction mixture, the reaction mixture was cooled to 0°C, and Compound XIII-1 (1.5 g) and copper(II) chloride (0.01 g) were added and stirred at 0°C for 24 hours. After extraction with hydrochloric acid and decane, the low-boiling point components were removed by reduced-pressure distillation, and 1.2 g of Compound XIII-2 was obtained by flash column chromatography using silica gel (developing solvent: decane).

[0259]

[0260] 1 H-NMR (400 MHz, CDCl3) δ 5.98 - 5.65 (m, 2H), 5.16 - 4.69 (m, 4H), 2.19 - 1.86 (m, 4H), 1.55 - 1.08 (m, 100H), 0.82-0.42 (m, 4H), 0.39 - -0.24 (m, 48H).

[0261] [Synthesis of Compound XIII-3] Compound XIII-2 (1.0 g) was dissolved in decane (10 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (2.5 g) were added, and the mixture was stirred at 50°C for 2 hours. By distilling off the low-boiling components under reduced pressure, 1.2 g of compound XIII-3 was obtained.

[0262]

[0263] 1 ​​H-NMR (400 MHz, CDCl3) δ 3.58 (s, 18H), 1.70 - 1.05 (m, 108H), 0.83 - 0.53 (m, 8H), 0.39 - -0.24 (m, 48H).

[0264] [Manufacturing and Evaluation of Articles] Articles were manufactured and evaluated using the above-mentioned compounds or compositions as surface treatment agents. The manufacturing method, water contact angle evaluation, abrasion resistance test, and evaluation criteria were carried out in the same manner as in Example 1 described above. The results are shown in Table 2.

[0265]

[0266] As shown in the results above, in equation (1), Z １ -Q １ [Z ２ -Si(R ３ ) ｎ L １ ３－ｎ Articles of Examples 6 to 9 and 12, which have a surface treatment layer using a compound having two or more structures represented by [ ], were found to have a higher water contact angle and better wear resistance compared to articles of Examples 10 to 11.

[0267] The articles of the present invention have excellent wear resistance. These articles can be used, for example, as display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automotive parts, and in nanoimprint technology. They can also be used as bodies, windows (windshields, side windows, rear windows), mirrors, bumpers, etc., in transportation equipment such as trains, automobiles, ships, and aircraft. Furthermore, they can be used as exterior walls of buildings, tents, solar power generation modules, sound insulation panels, concrete, and other outdoor items; fishing nets, insect nets, and aquariums. They can also be used as kitchen, bathroom, washbasin, mirror, and toilet-related parts; chandeliers, ceramics such as tiles; artificial marble, air conditioners, and various other indoor equipment. They can also be used as jigs, interior walls, and piping in factories. Additionally, they can be used as goggles, eyeglasses, helmets, slingshots, textiles, umbrellas, playground equipment, and soccer balls. Furthermore, they can be used as various packaging materials such as food packaging, cosmetic packaging, and the interior of pots. Furthermore, it can be used as an optical component in 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 equipment such as endoscopes, photocopiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and anti-reflective films.

[0268] This application claims priority based on Japanese Patent Application No. 2024-232224, filed on 27 December 2024, and incorporates all of its disclosures herein.

Claims

1. A compound represented by the following formula (1). R １１ ４－ｍ１－ｍ２ Si−[Q １１ (SiR １ ２ −O) ｐ１ −SiR １ ２ −Z １ −Q １ [Z ２ −Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ１ {Q １１ (SiR １ ２ −O) ｐ１ −SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ −O) ｐ１ −SiR １ ２ −Z １ −Q １ [Z ２ −Si(R ３ ) ｎ L １ ３－ｎ ] ｑ１ ] ｍ３ } ｍ２ …(1) However, １１ each R is independently a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue; １１ each Q is independently an oxygen atom or a hydrocarbon group; １ each R is independently a hydrocarbon group; １ each Z is independently an alkylene group which may have a divalent group between carbon atoms; １ Q is a single bond or a (1 + q1)-valent linking group; ２ each Z is independently a single bond or an alkylene group which may have a divalent group between carbon atoms; ３ each R is independently a hydrocarbon group; １ Each of the following is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group; each of the following is independently an integer from 0 to 2; each of the following is independently an integer of 0 or more; each of the following is independently an integer from 1 to 3; each of the following is independently an integer from 1 to 4; each of the following is independently an integer from 0 to 4; each of the following is independently an integer from 0 to 3; and each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 2: each of the following is independently an integer from 0 to 2: each of the following is independently an integer from 0 to 3: each of the following is independently an integer from 0 to 4 2. The compound according to claim 1, wherein p1 is an integer from 0 to 4.

3. Z mentioned above １ The compound according to claim 1, wherein is an alkylene group having 11 or more carbon atoms.

4. A method for producing the compound according to any one of claims 1 to 3, comprising reacting a compound represented by the following formula (1-1) with a compound represented by the following formula (1-2) to obtain a compound (1-3). R １１ ４－ｍ１－ｍ２ Si—[Q １１ (SiR １ ２ —O) ｐ１ H] ｍ１ {Q １１ (SiR １ ２ —O) ｐ１ —SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ —O) ｐ１ H] ｍ２ …(1-1) X １ —SiR １ ２ —Z １２ —X ２ …(1-2) R １１ ４－ｍ１－ｍ２ Si—[Q １１ (SiR １ ２ —O) ｐ１ —SiR １ ２ —Z １２ —X ２ ｍ１ {Q １１ (SiR １ ２ —O) ｐ１ —SiR １１ ３－ｍ３ [Q １１ (SiR １ ２ —O) ｐ１ —SiR １ ２ —Z １２ —X ２ ｍ２ …(1-3) However, R １１ is a hydrocarbon group, a trialkylsilyl group, or an organopolysiloxane residue, and Q １１ are each independently an oxygen atom or a hydrocarbon group, R １ ​Each of these is independently a hydrocarbon group, Z １２ Each of these is an alkylene group which may have a divalent group between carbon atoms, X １ X is a hydroxyl group or halogen atom. ２ is a group having a carbon-carbon double bond, or X １ It is a different halogen atom, p1 is a non-negative integer, q1 is a non-negative integer between 1 and 3, m1 is a non-negative integer between 1 and 4, m2 is a non-negative integer between 0 and 4, m3 is a non-negative integer between 0 and 3, and m1 + m3 (if there are multiple m3s, the sum of all m3s) is a non-negative integer between 3 and 4.

5. A composition comprising a compound according to any one of claims 1 to 3 and a liquid medium.

6. A composition comprising a compound according to any one of claims 1 to 3 and another compound having a reactive silyl group.

7. A surface treatment agent comprising the compound described in any one of claims 1 to 3.

8. A surface treatment agent comprising a compound according to any one of claims 1 to 3 and a liquid medium.

9. A surface treatment agent comprising a compound according to any one of claims 1 to 3 and another compound having a reactive silyl group.

10. An article comprising a base material and a surface treatment layer disposed on the base material and surface-treated with a surface treatment agent containing a compound according to any one of claims 1 to 3.

11. The article according to claim 10, which is an optical component.

12. The article according to claim 11, which is a display or touch panel.

13. A method for manufacturing an article, comprising surface-treating a substrate with a surface treatment agent containing a compound described in any one of claims 1 to 3, thereby producing an article in which a surface-treated layer is formed on the substrate.

Images