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

Abstract

Provided are a compound capable of forming a surface layer excellent in oil repellency and wear resistance, a method for producing the compound, a surface treatment agent, an article having a surface layer formed from the compound, and a method for producing the article. A compound according to the present invention includes a group represented by -{Si(Y1)(Y2)-L}m-{Si(Y1)(Y2)-CH2}-SiY3 3 and an organopolysiloxane residue. Y1 each independently are a hydrolyzable group or a hydroxyl group, Y2 each independently are a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, Y3 each independently are a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, at least one of Y3 is a hydrolyzable group or a hydroxyl group, L is -CH2 or an oxygen atom, and m is an integer of 0 or more.

Description

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

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

[0002] In various fields such as electrical and electronic materials, semiconductor materials, optical materials, construction materials, and automotive parts, there is known a method of forming a surface layer on the surface of a member (base material) for the purpose of suppressing adhesion of stains to the member used. For example, Patent Document 1 discloses a method of forming a surface layer on the surface of a base material using a surface treatment agent containing a silane compound represented by the following formula.

[0003]

[0004] International Publication No. WO 2024 / 034669

[0005] In recent years, the performance requirements for surface layers have increased, and depending on the application, there is a demand for surface layers excellent in oil repellency and abrasion resistance. When the present inventors evaluated a surface layer formed using the compound described in Patent Document 1, they found that the oil repellency and abrasion resistance of the surface layer were insufficient, and there was room for improvement.

[0006] The present invention has been made in view of the above problems, and an object of the present invention is to provide a compound capable of forming a surface layer excellent in oil repellency and abrasion resistance, a method for producing the compound, a surface treatment agent, an article having a surface layer formed from the compound, and a method for producing the article.

[0007] As a result of intensive studies on the above problems, the present inventors have found that the above problems can be solved by the following constitution. [1] A compound comprising a group represented by the following formula (P) and an organopolysiloxane residue. -{Si(Y １ )(Y ２ )-L} ｍ -{Si(Y １ )(Y ２ )-CH ２}-SiY ３ ３ (P) Provided that Y １ each independently represents a hydrolyzable group or a hydroxyl group, and Y ２Each of these is independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, Y ３ Each of these is independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and Y ３ At least one of them is a hydrolyzable group or a hydroxyl group, and L is -CH ２ -, or an oxygen atom, where m is an integer of 0 or more. [2] The compound described in [1], represented by the following formula (1) or the following formula (2). [R １１ - (Q) ｒ１ -Z １ ] ｐ１ - Q １ - (J １ ) ｎ２ (1) (J １ ) ｎ２ - Q ２ -Z ２ - Q ２ - (J １ ) ｎ２ (2) However, J １ Each of these is independently a group represented by the above formula (P), and R １１ Each of these is independently a group containing Si and not having a reactive silyl group, each of these is independently -O- or -OC(=O)-, each of these is independently 0 or 1, Z １ Each of these is independently a single bond, an alkylene group which may have an etheric oxygen atom, an organopolysiloxane group, or a combination of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group, Z ２ Q is a combination of an organopolysiloxane group, or an alkylene group which may have an etheric oxygen atom, and an organopolysiloxane group. １ is a (p1 + n2) valence linking group, Q ２ Each is independently a (1 + n2) valence linking group, p1 is an integer greater than or equal to 1, and each is independently an integer greater than or equal to 1, and in equation (1), at least one [R １１ - (Q) ｒ１ -Z １[1] contains an organopolysiloxane residue. [3] The compound according to [2], wherein n2 is 1 or 2 in formula (1) and formula (2) above. [4] A surface treatment agent comprising the compound according to any one of [1] to [3]. [5] The surface treatment agent according to [4] further comprising a liquid medium. [6] The surface treatment agent according to [4] or [5], which is an antifouling coating agent or a waterproof coating agent. [7] An article having a surface layer formed using the compound according to any one of [1] to [3] on the surface of a substrate. [8] The article according to [7], which is an optical component. [9] The article according to [7] or [8], which has the above surface layer on the surface of a component constituting the surface touched by a finger on a touch panel.

[10] A method for manufacturing an article, comprising forming a surface layer by a dry coating method using the surface treatment agent according to any one of [4] to [6].

[11] A method for manufacturing an article, comprising forming a surface layer by a wet coating method using the surface treatment agent according to any one of [4] to [6].

[12] A method for producing a compound, comprising reacting compound p1 represented by the following formula (p1) with compound p2 represented by the following formula (p2) to obtain compound p3 represented by the following formula (p3), and then reacting compound p3 with compound t1 having an organopolysiloxane residue and a group containing an unsaturated bond to obtain compound P10 containing a group represented by formula (P10) and an organopolysiloxane residue. SiCl ３ -CH ２ -SiCl ２ H (p1) C(Y １０ ) ３ H (p2) However, Y １０ These are each independently alkoxy groups. Si(Y １０ ) ３ -CH ２ -Si(Y １０ ) ２ H (p3) However, Y １０ As stated above, -Si(Y １０ ) ２ -CH ２ -Si(Y １０ ) ３ (P10) However, Y １０As stated above.

[0008] According to the present invention, it is possible to provide a compound capable of forming a surface layer with excellent oil repellency and abrasion resistance, a method for producing the compound, a surface treatment agent, an article having a surface layer formed from the compound, and a method for producing the article.

[0009] This is a schematic cross-sectional view showing an example of an article of the present invention.

[0010] The meanings of terms used in this invention are as follows: "Hydrogen group" refers to an aliphatic hydrocarbon group (such as a linear alkylene group, a branched alkylene group, or a cycloalkylene group), an aromatic hydrocarbon group (such as a phenylene group), or a group consisting of a combination thereof. "Surface layer" refers to a layer formed on the surface of a substrate. "Number average molecular weight" (Mn) is a value measured by size exclusion chromatography (gel permeation chromatography) using polystyrene as a standard substance. The "~" indicating a numerical range means that the values ​​written before and after it are included as the lower and upper limits, respectively. The bonding order in each divalent group is not limited unless otherwise specified. In this specification, when a compound or group is represented by a specific formula (X), the compound or group represented by formula (X) may be written as compound (X) or compound X, and group (X) or group X, respectively. When identical symbols exist in a single chemical formula, these identical symbols may represent identical structures or different structures within a defined range. In this specification, "Me" may represent a methyl group, "Et" may represent an ethyl group, and "Ph" may represent a phenyl group.

[0011] [Compound] The compound of the present invention (hereinafter referred to as "the compound") comprises a group represented by the following formula (P) (hereinafter referred to as "group P") and an organopolysiloxane residue.

[0012] - {Si(Y １ ) (Y ２ ) - L} ｍ - {Si(Y １ ) (Y ２ ) - CH ２}-SiY ３ ３ (P)

[0013] In formula (P), Y １ Each of these is independently a hydrolyzable group or a hydroxyl group, Y ２ Each of these is independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, Y ３ Each of these is independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and Y ３ At least one of them is a hydrolyzable group or a hydroxyl group, and L is -CH ２ - or an oxygen atom, where m is a non-negative integer.

[0014] This compound can form a surface layer with excellent oil repellency and abrasion resistance. The detailed reasons for this are still unknown, but it is presumed to be due to the following: In the case of a silane compound, such as the one described in Patent Document 1 above, if the hydrolyzable group that binds to the substrate has a branched structure, the molecular chains of the silane compound become difficult to arrange densely on the substrate. In contrast, in this compound, the group P does not have a branched structure that binds to the substrate, so it is thought that the molecular chains of this compound are arranged at a high density on the substrate. As a result, the number of liquid-repellent areas per unit area of ​​the surface layer increases, and it is presumed that the oil repellency of the surface layer is improved. Furthermore, when forming a surface layer using this compound, hydrolyzable groups or hydroxyl groups in the group P contained in adjacent molecular chains (specifically, {Si(Y １ ) (Y ２ ) - L} ｍ - {Si(Y １ ) (Y ２ ) - CH ２ It is presumed that the hydrolyzable groups (or hydroxyl groups) contained in the group represented by} react with each other to form siloxane bonds, resulting in improved wear resistance of the surface layer.

[0015] <Group P> The compound may contain only one group P, or two or more. In particular, from the viewpoint of achieving superior effects of the present invention, the number of groups P in the compound is preferably 1 to 6, more preferably 1 to 4, and especially preferably 1 to 2.

[0016] When there are multiple groups P in one molecule, the multiple groups P may be the same or they 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 groups P are the same.

[0017] Y １ Each of these is independently a hydrolyzable group or a hydroxyl group. Among them, Y is preferred because it exhibits superior effects in the present invention. １ It is preferable that the group is hydrolyzable.

[0018] Y １ In this context, the hydrolyzable group is a group that becomes a hydroxyl group through hydrolysis. That is, Si-Y 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.

[0019] Y １ Examples of hydrolyzable groups in this context include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, amino groups, isocyanate groups (-NCO), and -O-N=CR. ｒ ２ (R ｒ Each of these independently includes an alkyl group having 1 to 10 carbon atoms and an alkylene oxide-modified alkoxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 6, and more preferably 1 to 4. The number of carbon atoms in the aryloxy group is preferably 3 to 10. However, the aryl group of the aryloxy group may also be a heteroaryl group. The halogen atom is preferably a chlorine atom. The number of carbon atoms in the acyl group is preferably 1 to 6. The number of carbon atoms in the acyloxy group is preferably 1 to 6.

[0020] Among them, Y １ In this compound, the hydrolyzable group is preferably a carbon-1 to carbon-4 alkoxy group, an alkylene oxide-modified alkoxy group, or a halogen atom, from the viewpoint of ease of production. １An alkoxy group having 1 to 4 carbon atoms is preferred, and an ethoxy group or a methoxy group is more preferred, from the viewpoints of less outgassing during application and more excellent storage stability of the present compound.

[0021] Y ２ are each independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group. Among these, Y is preferably a hydrolyzable group from the viewpoint that the effect of the present invention is more excellent. ２ is preferably a hydrolyzable group.

[0022] Y ２ the hydrolyzable group in has the same definition as the hydrolyzable group in Y １ described above, and preferred embodiments are also the same.

[0023] Y ２ examples of the hydrocarbon group in include an alkyl group, a cycloalkyl group, an alkenyl group, an allyl group, and the like. An alkyl group is preferred from the viewpoint of ease of production of the present compound. The number of carbon atoms of the hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and still more preferably 1 to 2.

[0024] Y ３ are each independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and at least one of Y ３ is a hydrolyzable group or a hydroxyl group. Among these, Y is preferably a hydrolyzable group from the viewpoint that the effect of the present invention is more excellent. ３ is preferably a hydrolyzable group.

[0025] Y ３ the hydrolyzable group in has the same definition as the hydrolyzable group in Y １ described above, and preferred embodiments are also the same. Y ３ the hydrocarbon group in has the same definition as the hydrocarbon group in Y ２ described above, and preferred embodiments are also the same.

[0026] In the group P, Y that may be plural, Y that may be plural １ , Y that may be plural, Y ２ , and a plurality of Y ３Of these, at least two are hydrolyzable groups or hydroxyl groups. For superior effects of the present invention, the total number of hydrolyzable groups and hydroxyl groups in group P is preferably 2 to 100, more preferably 5 to 20, and even more preferably 5 to 10. For superior effects of the present invention, group P may have multiple Y groups. １ Y may have multiple properties. ２ , and multiple Y ３ Preferably, all of them are hydrolyzable groups or hydroxyl groups, and more preferably, all of them are hydrolyzable groups.

[0027] L is -CH ２ -, or an oxygen atom, and from the viewpoint that the effects of the present invention are superior, -CH ２ - is preferable.

[0028] m is an integer greater than or equal to 0, and is preferably 0 to 30, more preferably 0 to 5, and even more preferably 0 to 1, from the viewpoint of achieving superior effects of the present invention.

[0029] A specific example of the base P is -Si(OEt) ２ -CH ２ -Si(OEt) ３ , -Si(OCH ２ CH ２ OCH ３ ) ２ -CH ２ -Si(OCH) ２ CH ２ OCH ３ ) ３ , -Si(NMe ２ ) ２ -CH ２ -Si(NMe ２ ) ３、 -Si(Cl) ２ -CH ２ -Si(Cl) ３ , -Si(OMe) ２ -CH ２ -Si(OMe) ３ , -Si(OMe) ２ -CH ２ -Si(OMe) ２ -CH ２ -Si(OMe) ３ , -Si(OMe) ２ -CH２ -Si(OMe) ２ -CH ２ -Si(OMe) ２ -CH ２ -Si(OMe) ３ , -Si(OPh) ２ -CH ２ -Si(OPh) ３ These are some examples.

[0030] <Organopolysiloxane residues> This compound can form a surface layer with excellent oil repellency due to the presence of organopolysiloxane residues. Organopolysiloxane residues are -(Si-O) ｎｘ -Si- (where nx represents a number greater than or equal to 1), and for example, R in equation (1) described later. １１ Similar examples include the above.

[0031] <Preferred Embodiments of the Compound> From the viewpoint of achieving superior effects of the present invention, the compound represented by formula (1) (hereinafter referred to as "compound 1") or the compound represented by formula (2) (hereinafter referred to as "compound 2") is preferred.

[0032] (Compound 1 and Compound 2) Compound 1 is a compound represented by the following formula (1). Compound 2 is a compound represented by the following formula (2).

[0033] [R １１ - (Q) ｒ１ -Z １ ] ｐ１ - Q １ - (J １ ) ｎ２ (1) (J １ ) ｎ２ - Q ２ -Z ２ - Q ２ - (J １ ) ｎ２ (2)

[0034] However, J １ Each of these is independently the aforementioned base P, and R １１Each of these is independently a group containing Si and not having a reactive silyl group, each of these is independently -O- or -OC(=O)-, each of these is independently 0 or 1, Z １ Each of these is independently a single bond, an alkylene group which may have an etheric oxygen atom, an organopolysiloxane group, or a combination of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group, Z ２ Q is a combination of an organopolysiloxane group, or an alkylene group which may have an etheric oxygen atom, and an organopolysiloxane group. １ is a (p1 + n2) valence linking group, Q ２ Each is independently a (1 + n2) valence linking group, p1 is an integer greater than or equal to 1, and each is independently an integer greater than or equal to 1, and in equation (1), at least one [R １１ - (Q) ｒ１ -Z １ This includes organopolysiloxane residues.

[0035] R １１ Examples of groups containing Si and lacking a reactive silyl group include the groups represented by the following formulas (A1) to (A3). ａ２１ ３ M-(Q) ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２ - (A1)

[0036]

[0037] 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 Rｄ２１ 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 , R ｄ２２ , 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 Si, and Q ａ１１ is -O-, -C(=O)-, or an alkylene group having 1 to 6 carbon atoms, ta11 is an integer from 1 to 5, 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.

[0038] R ａ２１ , R ｂ２１ , R ｃ２１ , R ｄ２１ , R ｅ２１ , R ａ２４ , R ａ２５ and R ａ４１The 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.

[0039] R ｂ２２ , R ｃ２２ , R ｄ２２ , 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.

[0040] ta11 is MR ａ２４ ２ The number of repetitions of O is an integer from 1 to 5, preferably an integer from 1 to 3. M is Si. 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 1 to 100, and particularly preferably 1 to 50.

[0041] From equation (A1), (Q ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２ The following are specific examples of substructures excluding the one shown. However, * represents Q. ａ１１ This is the connection point.

[0042]

[0043] From equation (A2), (Q ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２The following are specific examples of substructures excluding the one shown. However, * represents Q. ａ１１ This is the connection point.

[0044]

[0045] From equation (A3), (Q ａ１１ ) ｚａ１ - (R ａＳｉ ) ｚａ２ The following are specific examples of substructures excluding the one shown. However, * represents Q. ａ１１ This is the connection point.

[0046]

[0047] R １１ If R is a group represented by the above formula (A1), ａ２１ ３ Three R's in M ａ２１ Of these, the number of trialkylsilyloxy groups is preferably two or less, from the viewpoint of achieving superior effects in the present invention.

[0048] Q is independently either -O- or -OC (=O)-, and r1 is either 0 or 1. Therefore, when r1 is 0, it is a single bond.

[0049] Z １ Each of these is independently a single bond, an alkylene group which may have an etheric oxygen atom, an organopolysiloxane group, or a combination of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group. ２ This is an organopolysiloxane group, or a combination of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group. Hereinafter, Z is used as a representative example. １ I will explain Z. ２ See below Z １ In this explanation, it is understood to be limited to combinations of an organopolysiloxane group, or an alkylene group which may have an etheric oxygen atom, and an organopolysiloxane group.

[0050] The alkylene group, which may have an etheric oxygen atom, may have one or more carbon atoms, and from the viewpoint of wear resistance, may have two or more carbon atoms, and more preferably four or more. The upper limit of the carbon number of the alkylene group is not particularly limited, but is 30 or less, and preferably 24 or less. The alkylene group in the compounds of this disclosure, which may have an etheric oxygen atom, may be linear, branched, or cyclic, with linear and branched being preferred, and linear being more preferred.

[0051] The organopolysiloxane group is preferably the following group (A6).

[0052] However, R ８ Each is independently a hydrocarbon group, k6 is a number greater than or equal to 1, j6 is 0 or 1, * is the Q-side bond, and ** is Q. １ This is a side joint. ２ In this case, * is one of the Q ２ The coupling on the side, ** is the Q on the other side ２ This is a side joint. R ８ Examples of hydrocarbon groups in this compound include alkyl groups, cycloalkyl groups, alkenyl groups, and aryl groups. From the viewpoint of ease of synthesis, saturated hydrocarbon groups are preferred, and alkyl groups are more preferred. ８ The number of carbon atoms is preferably 1 to 6, more preferably 1 to 3, and most preferably 1 or 2. k6 can be 1 or more, preferably 1 to 500, and more preferably 1 to 300.

[0053] Z １ and Z ２ From the standpoint of superior wear resistance of the surface layer, the alkylene group may have an etheric oxygen atom, and -(Si(R ８ ) ２ -O) ｍ -Si(R ８ ) ２ - is preferable. However, m is synonymous with k6 above, and R ８ Each of these is independently a hydrocarbon group, and is synonymous with the definition described above.

[0054] Examples of combinations of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group include the following groups (B1) to (B4).

[0055] *-R Ｓｉ -Ak １ -** (B1) *-Ak １ -R Ｓｉ -** (B2) *-Ak １ -R Ｓｉ -Ak １ -** (B3) *-R Ｓｉ -Ak １ -R Ｓｉ -** (B4)

[0056] However, Ak １ Each of these is an alkylene group which may independently have an etheric oxygen atom, and R Ｓｉ Each of these is independently the above-mentioned group (A6), * is the Q-side bond, and ** is Q. １ This is a side joint. ２ In this case, * is one of the Q ２ The coupling on the side, ** is the Q on the other side ２ It is a side joint.

[0057] Ak １ The alkylene group which may have an etheric oxygen atom may have one or more carbon atoms, and from the viewpoint of wear resistance, the number of carbon atoms is preferably two or more, and more preferably four or more. The upper limit of the number of carbon atoms of the alkylene group which may have an etheric oxygen atom is not particularly limited, but it is 50 or less, and preferably 40 or less. Ak １ The alkylene group in which an etheric oxygen atom may be present is preferably linear or branched, with linear being more preferred.

[0058] The combination of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group is preferably group (B1), group (B3), or group (B4) from the viewpoint of wear resistance, more preferably group (B1) or group (B4), and even more preferably group (B1) from the viewpoint of ease of manufacture.

[0059] Q １ is a (p1 + n2) valence linking group, Q ２This is a (1+n2) valence linking group. Hereafter, Q will be used as a representative example. １ I will explain the following. Q ２ The answer is Q below. １ In this explanation, p1 is understood to be limited to 1.

[0060] Q １ The group can be any group that does not impair the effects of the present disclosure, for example, an alkylene group which may have an etheric oxygen atom or a divalent organopolysiloxane group, a carbon atom, a nitrogen atom, a silicon atom, a divalent to octavalent organopolysiloxane group, and the groups (3-1A), (3-1B), (3-1A-1) to (3-1A-7) described later, J １ (That is, the groups excluding group P) are listed. However, Z １ Q １ If the terminal end that bonds with is an alkylene group, Q １ Z １ The terminal end that bonds with Z is not an alkylene group. １ If it is an organopolysiloxane group, Q １ Z １ Assume that the terminal end that binds to the other end is not an organopolysiloxane group.

[0061] Also, Q １ These may be groups (g2-1) to (g2-14) described later.

[0062] p1 is an integer greater than or equal to 1. From the viewpoint of superior wear resistance of the surface layer, p1 is preferably 1 to 6, and preferably 1 to 4.

[0063] n2 is an integer greater than or equal to 1. From the viewpoint of having superior oil-repellent properties of the surface layer, n2 is preferably 1 to 15, more preferably 1 to 6, and even more preferably 1 to 2.

[0064] -Q in equation (1) １ - (J １ ) ｎ２ The group represented is preferably (3-1A) or (3-1B), with group (3-1A) being more preferred.

[0065] - Q ａ -X ３１ (-Q ｂ -J１ ) ｈ (-R ３１ ) ｉ (3-1A) -Q ｃ - [CH ２ C(R) ３２ ) (-Q ｄ -J １ )] ｙ -R ３３ (3-1B) Q ａ is a single bond or a divalent linking group. However, Z １ Q １ If the terminal end that bonds with is an alkylene group, Q ａ Z １ The terminal end that bonds with Z is not an alkylene group. １ If it is an organopolysiloxane group, Q ａ Z １ The terminal end that bonds with the other is not an organopolysiloxane group. Examples of divalent linking groups include divalent hydrocarbon groups, divalent heterocyclic groups, -O-, -S-, and -SO ２ -, -N(R ｄ )-, -C(=O)-, -C(=S)-, -Si(R ａ ) ２ - and groups formed by combining two or more of these. The above-mentioned divalent hydrocarbon group may be a divalent saturated hydrocarbon group, a divalent aromatic hydrocarbon group which may have substituents, an alkenylene group, or an alkylylene group. The divalent saturated hydrocarbon group may be linear, branched, or cyclic, and an alkylene group is an example. The number of carbon atoms in the alkylene group is preferably 1 to 50, and more preferably 3 to 40. The divalent aromatic hydrocarbon group is preferably one with 5 to 20 carbon atoms, and an example is a phenylene group. In addition, alkenylene groups with 2 to 40 carbon atoms and alkylylene groups with 2 to 40 carbon atoms may also be used. The above-mentioned R ａ R is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group. ｄ This is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms). Examples of groups formed by combining two or more of these include -OC(=O)-, -C(=O)O-, -C(=O)S-, and -C(=O)N(R).ｄ )-,-N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-,-N(R ｄ )C(=O)O-, -OC(=O)N(R ｄ ) -, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -C(=O)N(R ｄ )- an alkylene group having -N(R ｄ ) an alkylene group having C(=O)-, -OC(=O)N(R ｄ Alkylene group having - )-, alkylene group having an etheric oxygen atom, alkylene group having -S-, alkylene group having -OC(=O)-, alkylene group having -C(=O)O-, alkylene group having -C(=O)S-, -N(R ｄ )- an alkylene group having -N(R ｄ )C(=O)N(R ｄ ) an alkylene group having -SO ２ N(R) ｄ )- an alkylene group having an alkylene group-Si(R ａ ) ２ - Phenylene group - Si (R ａ ) ２ - is one example. Among them, Z １ Q １ If the terminal end that bonds with is an alkylene group, Q ａ These include divalent hydrocarbon groups other than alkylene groups, divalent heterocyclic groups, -O-, -S-, and -SO ２ -, -N(R ｄ )-, -C(=O)-, -Si(R ａ ) ２ -, -OC(=O)-, -C(=O)O-, -C(=O)S-, -C(=O)N(R ｄ )-,-N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-,-N(R ｄ )C(=O)O-, -OC(=O)N(R ｄ ) -, -SO ２ N(R)ｄ )-,-N(R ｄ ) SO ２ -, -C(=O)N(R ｄ )- an alkylene group having -N(R ｄ ) an alkylene group having C(=O)-, -OC(=O)N(R ｄ Alkylene group having - )-, alkylene group having an etheric oxygen atom, alkylene group having -S-, alkylene group having -OC(=O)-, alkylene group having -C(=O)O-, alkylene group having -C(=O)S-, -N(R ｄ )- an alkylene group having -N(R ｄ )C(=O)N(R ｄ ) an alkylene group having - or -SO ２ N(R) ｄ An alkylene group having -OC(=O)-, -C(=O)N(R ｄ )- an alkylene group having -OC(=O)N(R ｄ Alkylene group having -, alkylene group having an etheric oxygen atom, alkylene group having -S-, alkylene group having -C(=O)O-, alkylene group having -C(=O)S-, -N(R ｄ )- an alkylene group having -N(R ｄ )C(=O)N(R ｄ More preferably, an alkylene group having -C(=O)O-, or -C(=O)N(R ｄ )- an alkylene group having -N(R ｄ Alkylene groups having C(=O)- and -OC(=O)- are even more preferred. １ If it is an organopolysiloxane group, Q ａ This includes a divalent hydrocarbon group which may have an etheric oxygen atom, a divalent heterocyclic group, and -SO ２ -, -C(=O)-, -Si(R ａ ) ２ -, -C(=O)O-, -OC(=O)-, -C(=O)S-, -C(=O)N(R ｄ ) -, -SO ２ N(R) ｄ )-, -C(=O)N(R ｄ)- alkylene group having -C(=O)O-, -N(R ｄ ) Alkylene group having C(=O)-, alkylene group having -OC(=O)-, -SO ２ N(R) ｄ )- an alkylene group having an alkylene group-Si(R ａ ) ２ - Phenylene group - Si (R ａ ) ２ - is preferable.

[0066] In formula (3-1A), X ３１ This is a group having a single bond, an alkylene group, a carbon atom, a nitrogen atom, a silicon atom, a 2-8 valent organopolysiloxane group, or a (h+i+1) valent ring. However, Z １ Q １ The terminal end that bonds with is an alkylene group, and Q ａ If it is a single bond, X ３１ Z １ The terminal end that bonds with is not an alkylene group. Also, Z １ is an organopolysiloxane group, and Q ａ If it is a single bond, X ３１ The terminal end that bonds with Z is not an organopolysiloxane group. In all other cases, X ３１ The terminal end may be an alkylene group or an organopolysiloxane group. The alkylene group may have -O-, a sylphenylene skeleton, a divalent organopolysiloxane group, or a dialkylsilylene group. The alkylene group may have multiple groups selected from the group consisting of -O-, a sylphenylene skeleton, a divalent organopolysiloxane group, and a dialkylsilylene group. ３１ The number of carbon atoms in the alkylene group represented by is preferably 1 to 20, and more preferably 1 to 10. Examples of divalent to octavalent organopolysiloxane groups include divalent organopolysiloxane groups.

[0067] In formula (3-1A), X ３１ If is a group having a (h+i+1) valent ring, Q ａ , (-Q ｂ -J １ ) and R ３１It is directly bonded to the atoms constituting the ring. However, the ring is a ring other than an organopolysiloxane ring. ３１ The ring in the expression may be a monoring, a fused polyring, a bridging ring, a spiroring, or an aggregated polyring. The atoms constituting the ring may be a carbon ring consisting only of carbon atoms, or a heteroring consisting of a heteroatom with a valence of 2 or more and a carbon atom. The bonds between the atoms constituting the ring may be single bonds or multiple bonds. Furthermore, the ring may be aromatic or a non-aromatic ring. As a monoring, a 4-membered to 8-membered ring is preferred, and a 5-membered or 6-membered ring is more preferred. As a fused polyring, a fused polyring formed by the fusion of two or more 4-membered to 8-membered rings is preferred, and a fused polyring formed by the bonding of two or three rings selected from 5-membered and 6-membered rings, or a fused polyring formed by the bonding of one or two rings selected from 5-membered and 6-membered rings and one 4-membered ring is more preferred. As the bridging ring, a bridging ring with a 5-membered or 6-membered ring as the largest ring is preferred, and as the spiro ring, a spiro ring consisting of two 4-membered to 6-membered rings is preferred. As the aggregated polyring, an aggregated polyring in which two or three rings selected from the 5-membered and 6-membered rings are bonded via single bonds, one to three carbon atoms, or one heteroatom with a valency of 2 or 3 is preferred. In the aggregated polyring, each ring has Q ａ , (-Q ｂ -J １ ) and R ３１ It is preferable that one of the following (when i = 1 or greater) is bonded. The heteroatoms constituting the ring are preferably nitrogen atoms, oxygen atoms, or sulfur atoms, and more preferably nitrogen atoms or oxygen atoms. It is preferable that the number of heteroatoms constituting the ring is three or less. Furthermore, if the number of heteroatoms constituting the ring is two or more, those heteroatoms may be different.

[0068] X ３１The preferred rings in the compound are those 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 1,3-cyclohexadiene rings, 1,4-cyclohexadiene rings, anthracene rings, cyclopropane rings, decahydronaphthalene rings, norbornene rings, norbornadiene rings, furan rings, pyrrole rings, thiophene rings, pyrazine rings, morpholine rings, aziridine rings, isoquinoline rings, oxazole rings, isoxazole rings, thiazole rings, imidazole rings, pyrazole rings, pyran rings, pyridazine rings, pyrimidine rings, and indene rings. Rings containing an oxo group (=O) are also shown below.

[0069]

[0070] X ３１ In this case, the bonds between atoms that make up a ring that do not form a ring are Q ａ , (-Q ｂ -J １ ) or R ３１ This is a bond that connects to Q. If there are any remaining bonds, these bonds are attached to a hydrogen atom or a substituent. Examples of such substituents include halogen atoms, alkyl groups (which may contain an etheric oxygen atom between carbon atoms), cycloalkyl groups, alkenyl groups, allyl groups, alkoxy groups, and oxo groups (=O). In addition, one of the carbon atoms constituting the ring may be Q. ａ , (-Q ｂ -J １ ) or R ３１ If it has two bonding bonds, one of the carbon atoms is Q ａ and (-Q ｂ -J １) and may be joined together, and two (-Q ｂ -J １ ) may be joined together. Q ａ And, (-Q ｂ -J １ ) or R ３１ It is preferable that it is bonded to a different ring-constituting atom. h (-Q ｂ -J １ Each of these may be bonded to a separate ring-forming atom, two of which may be bonded to one ring-forming carbon atom, and two of these may be bonded to two (-Q ｂ -J １ There may be two or more ring-forming carbon atoms to which ) are bonded. i R ３１ Each of these may be bonded to a separate ring-forming atom, two of which may be bonded to one ring-forming carbon atom, and two R ３１ There may be two or more ring-forming carbon atoms to which the compound is bonded.

[0071] Among them, X ３１ From the standpoint of superior wear resistance of the surface layer, carbon atoms, nitrogen atoms, silicon atoms, 4-8 valent organopolysiloxane groups, or groups having a (h+i+1) valent ring are preferred, with carbon atoms being more preferred.

[0072] In equation (3-1A), Q ｂ It is a single bond or a divalent linking group. The definition of a divalent linking group is given in Q above. ａ This is synonymous with the definition explained earlier. However, Z １ Q １ The terminal end that bonds with is an alkylene group, and Q ａ and X ３１ If it is a single bond, Q ｂ Z １ The terminal end that bonds with is not an alkylene group. Also, Z １ is an organopolysiloxane group, and Q ａ and X ３１ If it is a single bond, Q ｂ Z １ The terminal end that binds to it is not an organopolysiloxane group. In all other cases, Q ｂ The terminal end may be an alkylene group or an organopolysiloxane group.

[0073] Among them, Q ｂ The alkylene group is preferably an alkylene group which may have an etheric oxygen atom. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may be 2 to 11, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10.

[0074] In formula (3-1A), R ３１ This is a hydrogen atom, a hydroxyl group, or an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.

[0075] X ３１ When it is a single bond or an alkylene group, h is 1 and i is 0, X ３１ If it is a nitrogen atom, then h is an integer from 1 to 2, i is an integer from 0 to 1, and the equation h + i = 2 is satisfied, X ３１ If the atom is a carbon atom or a silicon atom, then h is an integer from 1 to 3, i is an integer from 0 to 2, and the equation h + i = 3 is satisfied. ３１ If the organopolysiloxane group is divalent to octavalent, then h is an integer from 1 to 7, i is an integer from 0 to 6, and the equation h + i = 1 to 7 is satisfied. ３１ If the group has a ring with (h+i+1) valencies, then h is an integer from 1 to 7, i is an integer from 0 to 6, and the equation h+i=1 to 7 is satisfied. (-Q ｂ -J １ If there are two or more (-Q) then ｂ -J １ ) may be the same or different. ３１ If there are two or more (-R ３１ These may be the same or different.

[0076] In particular, i is preferably 0 because it offers superior wear resistance to the surface layer.

[0077] In equation (3-1A), Q ａ , X ３１ , and Q ｂ If it is a single bond, J １ is, Z １ It is directly bonded with Z１ J inside １ The side group is an alkylene group.

[0078] In formula (3-1B), Q ｃ is a single bond or a divalent linking group. However, Z １ Q １ If the terminal end that bonds with is an alkylene group, Q ｃ Z １ The end that bonds with it is not an alkylene group. １ If it is an organopolysiloxane group, Q ｃ The terminal end that bonds with Z is not an organopolysiloxane group. The definition of a divalent linking group is as described above for Q. ａ This is synonymous with the definition explained earlier.

[0079] In formula (3-1B), R ３２ This is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and a hydrogen atom is preferred because it facilitates the production of this compound. A methyl group is preferred as the alkyl group.

[0080] In formula (3-1B), Q ｄ Q is a single bond or an alkylene group. The number of carbon atoms in the alkylene group is preferably 1 to 10, and more preferably 1 to 6. From the standpoint of ease of production of this compound, ｄ This is a single bond or -CH ２ - is preferable.

[0081] In formula (3-1B), R ３３ This atom is either a hydrogen atom or a halogen atom, and a hydrogen atom is preferred because it facilitates the production of this compound.

[0082] y is an integer between 1 and 10, preferably between 1 and 6. Two or more [CH ２ C(R) ３２ ) (-Q ｄ -J １ ) ] may be the same or different.

[0083] The following groups (3-1A-1) to (3-1A-7) are preferred as the group (3-1A). - (X ３２ ) ｓ１ - Q ｂ１ -J１ (3-1A-1) -(X ３３ ) ｓ２ - Q ａ２ -N[-Q ｂ２ -J １ ] ２ (3-1A-2) -Q ａ３ -Si(R ｇ ) [-Q ｂ３ -J １ ] ２ (3-1A-3) -[Q ｅ ] ｓ４ - Q ａ４ - (O) ｔ４ -C[-(O) ｕ４ - Q ｂ４ -J １ ] ３－ｗ１ (-R ３１ ) ｗ１ (3-1A-4) -Q ａ５ -Si[-Q] ｂ５ -J １ ] ３ (3-1A-5) -[Q ｅ ] ｖ - Q ａ６ -Z ａ [-Q] ｂ６ -J １ ] ｗ２ (3-1A-6) -[Q ｅ ] ｓ４ - Q ａ４ - (O) ｔ４ -Z ｃ [-(O-Q) ｂ４ ) ｕ４ -J １ ] ｗ３ (-OH) ｗ４ (3-1A-7) However, Z １ Q １ If the terminal end that bonds with is an alkylene group, then the Z of the groups (3-1A-1) to (3-1A-7) １ The terminal end that bonds with is not an alkylene group. Also, Z １ If it is an organopolysiloxane group, then Z of groups (3-1A-1) to (3-1A-7) １ The terminal end that binds to the other end is not an organopolysiloxane group.

[0084] Among these, group (3-1A) is more preferably group (3-1A-1) or group (3-1A-4), with group (3-1A-1) being more preferable, in terms of achieving superior effects of the present invention.

[0085] In the base (3-1A-1), X ３２ is, -Ph １ -, -Ph １ -O-, -Ph １ -Ph １ -, -Ph １ -Ph １ -Ph １ -, -Ph １ -O-Ph １ -, -Ph １ -O-Ph １ -O-Ph １ -, -O-, -S-, -N(R ｄ )-, -C(=O)-, -C(=O)O-, -C(=O)S-, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-, -OC(=O)N(R ｄ )-, or-C(=O)N(R ｄ )-, -OC (=O)-. R ｄ The definition is as stated above. １ is a phenylene group which may have substituents. s1 is 0 or 1.

[0086] Among them, Z １ Q １ If the terminal end that bonds with is an alkylene group, X ３２ is -O-, -S-, -N(R ｄ )-, -C(=O)-, -C(=O)O-, -C(=O)S-, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-, -OC(=O)N(R ｄ)-, or-C(=O)N(R ｄ )- is preferred, -O-, -S-, -N(R ｄ )-, -C(=O)O-, -C(=O)S-, -N(R ｄ )C(=O)N(R ｄ )-, -OC(=O)N(R ｄ )-, or-C(=O)N(R ｄ )- is more preferable, -C(=O)O- or -C(=O)N(R ｄ ) - is even more preferable. Z １ If it is an organopolysiloxane group, X ３２ is, -Ph １ -, -Ph １ -O-, -Ph １ -Ph １ -, -Ph １ -Ph １ -Ph １ -, -Ph １ -O-Ph １ -, -Ph １ -O-Ph １ -O-Ph １ -, -C(=O)O-, -OC(=O)-, -C(=O)S-, -SO ２ N(R) ｄ )-, or-C(=O)N(R ｄ )-,-N(R ｄ )C(=O)- is preferred.

[0087] Q ｂ１ This is a single bond or an alkylene group. The alkylene group may have -O-, a sylphenylene skeleton group, or a dialkylsilylene group. The alkylene group may have multiple groups selected from the group consisting of -O-, a sylphenylene skeleton group, a divalent organopolysiloxane group, and a dialkylsilylene group. When the alkylene group has -O-, a sylphenylene skeleton group, a divalent organopolysiloxane group, or a dialkylsilylene group, it is preferable that these groups are located between carbon atoms. Q ｂ１ The number of carbon atoms in the alkylene group represented by is preferably 1 to 50, and more preferably 3 to 40. Alternatively, the number of carbon atoms may be 1 to 10.

[0088] Z １ Q１ When the terminal end that bonds with is an alkylene group, specific examples of the group (3-1A-1) include the following group. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0089]

[0090] Z １ When is an organopolysiloxane group, specific examples of the group (3-1A-1) include the following groups. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0091]

[0092] In the base (3-1A-2), X ３３ is -O-, -S-, -N(R ｄ )-, -C(=O)-, -C(=O)O-, -C(=O)S-, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-, -OC(=O)N(R ｄ )-, or-C(=O)N(R ｄ ) - is R ｄ The definition is as described above. s2 is either 0 or 1. s2 is preferably 0 from the standpoint of facilitating the production of this compound.

[0093] Among them, Z １ Q １ If the terminal end that bonds with is an alkylene group, X ３３ is -O-, -S-, -N(R ｄ )-, -C(=O)-, -C(=O)O-, -C(=O)S-, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-, -OC(=O)N(R ｄ)-, or-C(=O)N(R ｄ ) - is preferable. Z １ If it is an organopolysiloxane group, X ３３ -C(=O)O-, -C(=O)S-, -SO ２ N(R) ｄ )-, or-C(=O)N(R ｄ ) - is preferable.

[0094] Q ａ２ This includes single bonds, alkylene groups, -C(=O)-, or etheric oxygen atoms between carbon atoms of alkylene groups with 2 or more carbon atoms, -C(=O)-, -C(=O)O-, -OC(=O)-, and -C(=O)N(R). ｄ )-,-N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-,-N(R ｄ )C(=O)O-, -OC(=O)N(R ｄ ) -, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -C(=O)N(R ｄ ) - or -NH- is a group having this property. Q ａ２ The number of carbon atoms in the alkylene group represented by is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 3. Q ａ２ An alkylene group with 2 or more carbon atoms represented by an etheric oxygen atom between carbon atoms, -C(=O)-, -C(=O)O-, -OC(=O)-, -C(=O)N(R) ｄ )-,-N(R ｄ )C(=O)-,-N(R ｄ )C(=O)N(R ｄ )-,-N(R ｄ )C(=O)O-, -OC(=O)N(R ｄ ) -, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -C(=O)N(R ｄ The number of carbon atoms in the group having - or -NH- is preferably 2 to 10, and more preferably 2 to 6.

[0095] Q ａ２ From the standpoint of facilitating the production of this compound, a single bond or -C(=O)- is preferred.

[0096] Q ｂ２ This refers to an alkylene group, or a group having a divalent organopolysiloxane group, an etheric oxygen atom, or -NH- between carbon atoms of an alkylene group having two or more carbon atoms. Q ｂ２ The number of carbon atoms in the alkylene group represented by is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6. For example, 2, 3, 8, 9, and 11 are given. Also, the above number of carbon atoms may be 1 to 10. Q ｂ２ The number of carbon atoms in the group having a divalent organopolysiloxane group, an etheric oxygen atom, or -NH- between carbon atoms of the alkylene group with 2 or more carbon atoms represented by is preferably 2 to 10, and more preferably 2 to 6.

[0097] Q ｂ２ As for the ease of producing this compound, -CH ２ CH ２ CH ２ -ien-CH ２ CH ２ OCH ２ CH ２ CH ２ - is preferable (however, the right side is J) １ (Combine.)

[0098] Two [-Q ｂ２ -J １ These may be the same or different.

[0099] Z １ Q １ When the terminal end that bonds with is an alkylene group, specific examples of the group (3-1A-2) include the following group. In the formula below, * represents Z １ This indicates the bonding position with. Also, in the formula, J １ (CH ２ ) αIn this formula, α is an integer representing the number of methylene groups, preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. The number of carbon atoms may also be 1 to 10. Multiple αs contained in the same compound may be the same or different.

[0100]

[0101] Z １ If the group is an organopolysiloxane group, specific examples of the group (3-1A-2) include the following groups. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0102]

[0103] In the base (3-1A-3), Q ａ３ This is an alkylene group which may have a single bond or an etheric oxygen atom. Q is chosen because it is easy to produce this compound. ａ３ A single bond is preferred. The number of carbon atoms in the alkylene group, which may have an etheric oxygen atom, is preferably 1 to 10, and particularly preferably 2 to 6.

[0104] R ｇ R is a hydrogen atom, a hydroxyl group, or an alkyl group. ｇ From the standpoint of ease of production, hydrogen atoms or alkyl groups are preferred. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably a methyl group.

[0105] Q ｂ３ This refers to an alkylene group, or a group having an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms of an alkylene group having two or more carbon atoms. Q ｂ３ The number of carbon atoms in the alkylene group represented by is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6. For example, 2, 3, 8, 9, and 11 are given. Also, the above number of carbon atoms may be 1 to 10. Q ｂ３The number of carbon atoms in the alkylene group having two or more carbon atoms, represented by [the formula], which has an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms, is preferably 2 to 20, and more preferably 2 to 11. ｂ３ Because this compound is easy to produce, -CH ２ CH ２ -ien-CH ２ CH ２ CH ２ -, or -CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ - is preferable.

[0106] Two [-Q ｂ３ -J １ These may be the same or different.

[0107] Z １ Q １ When the terminal end that bonds with is an alkylene group, specific examples of the group (3-1A-3) include the following group. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0108]

[0109] Z １ If the group is an organopolysiloxane group, specific examples of the group (3-1A-3) include the following groups. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0110]

[0111] In the base (3-1A-4), Q ｅ is -C(=O)O-, -SO ２ N(R) ｄ )-,-N(R ｄ ) SO ２ -, -N(R ｄ )C(=O)-, -OC(=O), or -C(=O)N(R ｄ) - is R ｄ The definition is as stated above. R ３１ The definition is as described above. If w1 is 1 or 2, R ３１ It is preferably a hydrogen atom. s4 is 0 or 1. Q ａ４ This is an alkylene group which may have a single bond or an etheric oxygen atom. The number of carbon atoms in the alkylene group which may have an etheric oxygen atom is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 3. t4 is 0 or 1 (however, Q ａ４ It is 0 if it is a single bond. ) -Q ａ４ - (O) ｔ４ - As for the ease of producing this compound, if s4 is 0, it is a single bond, -CH ２ O-, -CH ２ OCH ２ -ien-CH ２ OCH ２ CH ２ O-, -CH ２ OCH ２ CH ２ OCH ２ -ien-CH ２ OCH ２ CH ２ CH ２ CH ２ OCH ２ - is preferred, and if s4 is 1, a single bond, -CH ２ -ien-CH ２ CH ２ - is preferable.

[0112] Q ｂ４ is an alkylene group, and the above alkylene group is -O-, -C(=O)N(R ｄ ) - (R ｄ The definition is as described above. It may have a silphenylene skeleton group, a divalent organopolysiloxane group, or a dialkylsilylene group. When the alkylene group has -O- or a silphenylene skeleton group, it is preferable that the -O- or silphenylene skeleton group is between carbon atoms. Also, the alkylene group may have -C(=O)N(R ｄ)-, if it has a dialkylsilylene group or a divalent organopolysiloxane group, carbon-carbon or (O) ｕ４ It is preferable to have these groups at the terminal end that bonds with the other. ｂ４ The number of carbon atoms in the alkylene group represented by is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6. For example, 2, 3, 8, 9, and 11 are given. The above number of carbon atoms may also be 1 to 10.

[0113] u4 is either 0 or 1. - (O) ｕ４ - Q ｂ４ -As for the ease of producing this compound, -CH ２ CH ２ -ien-CH ２ CH ２ CH ２ -ien-CH ２ OCH ２ CH ２ CH ２ -ien-CH ２ OCH ２ CH ２ CH ２ CH ２ CH ２ -, -OCH ２ CH ２ CH ２ -, -OSi(CH ３ ) ２ CH ２ CH ２ CH ２ -, -OSi(CH ３ ) ２ OSi(CH ３ ) ２ CH ２ CH ２ CH ２ -ien-CH ２ CH ２ CH ２ Si(CH ３ ) ２ PhSi(CH ３ ) ２ CH ２ CH ２ - is preferable (however, the right side is J) １ (Combine.)

[0114] w1 is an integer between 0 and 2, preferably 0 or 1. [-(O) ｕ４ - Q ｂ４ -J １ If there are two or more [-(O)] ｕ４ - Q ｂ４ -J １ ] may be the same or different. ３１ If there are two or more (-R ３１ These may be the same or different.

[0115] Z １ Q １ When the terminal end that bonds with is an alkylene group, specific examples of the group (3-1A-4) include the following groups. In the following formulas, * represents Z １ This indicates the connection point with [the other element].

[0116]

[0117] Z １ If the group is an organopolysiloxane group, specific examples of the group (3-1A-4) include the following groups. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0118]

[0119] In the base (3-1A-5), Q ａ５ This is an alkylene group which may have an etheric oxygen atom. The number of carbon atoms in the alkylene group which may have an etheric oxygen atom is preferably 1 to 10, and particularly preferably 2 to 6. Q ａ５ As for the ease of producing this compound, -OCH ２ CH ２ CH ２ -, -OCH ２ CH ２ OCH ２ CH ２ CH ２ -ien-CH ２ CH ２ -ien-CH ２ CH ２ CH ２ - is preferable (however, the right side is J) １ (Combine.)

[0120] Q ｂ５ This refers to an alkylene group, or a group having an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms of an alkylene group having two or more carbon atoms. Q ｂ５ The number of carbon atoms in the alkylene group represented by is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6. For example, 2, 3, 8, 9, and 11 are given. Also, the above number of carbon atoms may be 1 to 10. Q ｂ５ The number of carbon atoms in the alkylene group having two or more carbon atoms, represented by the formula, is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6. ｂ５ As for the ease of producing this compound, -CH ２ CH ２ CH ２ -ien-CH ２ CH ２ OCH ２ CH ２ CH ２ - is preferable (however, the right side is J) １ (Combine.)

[0121] 3 [-Q ｂ５ -J １ These may be the same or different.

[0122] Z １ Q １ When the terminal end that bonds with is an alkylene group, specific examples of the group (3-1A-5) include the following groups. In the following formulas, * represents Z １ This indicates the connection point with [the other element].

[0123]

[0124] Z １ If the group is an organopolysiloxane group, specific examples of the group (3-1A-5) include the following groups. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0125]

[0126] Q in the base (3-1A-6) ｅ The definition of is as defined in the above-mentioned base (3-1A-4). v is either 0 or 1.

[0127] Q ａ６ This is an alkylene group which may have an etheric oxygen atom. The number of carbon atoms in the alkylene group which may have an etheric oxygen atom is preferably 1 to 10, and particularly preferably 2 to 6. Q ａ６ As for the ease of producing this compound, -CH ２ OCH ２ CH ２ CH ２ -ien-CH ２ OCH ２ CH ２ OCH ２ CH ２ CH ２ -ien-CH ２ CH ２ -ien-CH ２ CH ２ CH ２ - is preferable (however, the right side is Z) ａ (Combine.)

[0128] Z ａ is a (w²+1) valent organopolysiloxane group, or a (w²+1) valent group having an alkylene group between organopolysiloxane groups. w² is an integer from 2 to 7. Examples of (w²+1) valent organopolysiloxane groups and (w²+1) valent groups having an alkylene group between organopolysiloxane groups are listed below. However, R in the following formula ａ This is as described above. * indicates the binding site.

[0129]

[0130] Q ｂ６ This refers to an alkylene group, or a group having an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms of an alkylene group having two or more carbon atoms. Q ｂ６The number of carbon atoms in the alkylene group represented by is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6. For example, 2, 3, 8, 9, and 11 are given. Also, the above number of carbon atoms may be 1 to 10. Q ｂ６ The number of carbon atoms in the alkylene group having two or more carbon atoms, represented by the formula, is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6. ｂ６ As for the ease of producing this compound, -CH ２ CH ２ -ien-CH ２ CH ２ CH ２ - is preferable. Two [-Q] ｂ６ -J １ These may be the same or different.

[0131] Specific examples of the base (3-1A-6) include the following base. In the following formula, * represents Z １ This indicates the connection point with [the other element].

[0132]

[0133] In base (3-1A-7), Z ｃ w3 is a (w3 + w4 + 1) valent hydrocarbon group. w3 is an integer greater than or equal to 4. w4 is an integer greater than or equal to 0. Q ｅ s4, Q ａ４ t4, Q ｂ４ The definitions and preferred ranges of u4 are the same as the definitions of each symbol in base (3-1A-4).

[0134] Z ｃ It may consist of a hydrocarbon chain, and may have etheric oxygen atoms between carbon atoms in the hydrocarbon chain; it is preferable that it consists of a hydrocarbon chain. ｃ The valency is preferably 5 to 20, more preferably 5 to 10, even more preferably 5 to 8, and particularly preferably 5 to 6. ｃpreferably has 3 to 50 carbon atoms, more preferably 4 to 40 carbon atoms, still more preferably 5 to 30 carbon atoms. w3 is preferably 4 to 20, more preferably 4 to 16, still more preferably 4 to 8, and particularly preferably 4 to 5. w4 is preferably 0 to 10, more preferably 0 to 8, still more preferably 0 to 6, particularly preferably 0 to 3, and most preferably 0 to 1. [-(O-Q ｂ４ ) ｕ４ -J １ is two or more in number, the two or more [-(O-Q ｂ４ ) ｕ４ -J １ may be the same or different from each other.

[0135] Z １ has Q １ side terminal being an alkylene group, specific examples of the group (3-1A-7) include the following groups. In the following formulae, * represents a bonding position to Z １ .

[0136]

[0137] Z １ has Q １ side terminal being an organopolysiloxane group, specific examples of the group (3-1A-7) include the following groups. In the following formulae, * represents a bonding position to Z １ .

[0138]

[0139] Q １ may be group (g2-1) (with the proviso that p1=d1+d3 and n2=d2+d4), group (g2-2) (with the proviso that p1=e1 and n2=e2), group (g2-3) (with the proviso that p1=1 and n2=2), group (g2-4) (with the proviso that p1=h1 and n2=h2), group (g2-5) (with the proviso that p1=i1 and n2=i2), group (g2-6) (with the proviso that p1=1 and n2=1), or group (g2-7) (with the proviso that p1=1 and n2=i3).

[0140]

[0141] (-A １ -Q １２ -)ｅ１ C(R) ｅ２ ) ４－ｅ１－ｅ２ (-Q ２２ -) ｅ２ (g2-2) -A １ - Q １３ -N(-Q) ２３ -) ２ (g2-3) (-A １ - Q １４ -) ｈ１ Z(-Q) ２４ -) ｈ２ (g2-4) (-A １ - Q １５ -) ｉ１ Si(R ｅ３ ) ４－ｉ１－ｉ２ (-Q ２５ -) ｉ２ (g2-5) -A １ - Q ２６ - (g2-6) -A １ - Q １２ -CH(-Q) ２２ -)-Si(R ｅ３ ) ３－ｉ３ (-Q ２５ -) ｉ３ (g2-7)

[0142] However, in equations (g2-1) to (g2-7), A １ The side is Z １ Combined with Q ２２ Q ２３ Q ２４ Q ２５ Or Q ２６ J １ It combines with A. １ This is a single bond, -C(=O)NR ｅ６ -, -C(=O)-, -OC(=O)O-, -NHC(=O)O-, -NHC(=O)NR ｅ６ -, -O-, or SO ２ NR ｅ６ - is Z １ A １ If the terminal end that bonds with is an alkylene group, A １ Z １ The terminal end that bonds with is not an alkylene group. Also, Z １ If it is an organopolysiloxane group, A１ of Z １ the terminal end on the bonding side is not an organopolysiloxane group. Q １２ is a single bond, an alkylene group, or a group having -C(=O)NR between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms ６ -, -C(=O)-, -NR ６ - or -O-, and when two or more Q １２ are present, the two or more Q １２ may be the same or different. Q １３ is a single bond, an alkylene group, or a group having -C(=O)NR between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms ６ -, -C(=O)-, -NR ６ - or -O-, or a group having -C(=O)- at the N-side terminal end of an alkylene group. Q １４ is Q １４ when the atom in Z to which Q １２ binds is a carbon atom, and is Q １４ when the atom in Z to which Q １３ binds is a nitrogen atom, and when two or more Q １４ are present, the two or more Q １４ may be the same or different. Q １５ is an alkylene group, or a group having -C(=O)NR between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms ６ -, -C(=O)-, -NR ６ - or -O-, and when two or more Q １５ are present, the two or more Q １５ may be the same or different. Q ２２ is an alkylene group, a group having -C(=O)NR between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms ６ -, -C(=O)-, -NR ６ - or -O-, a group having -C(=O)NR at the terminal end of an alkylene group on the side not connected to J １ -, -C(=O)-, -NR ６ - or -O-, or -C(=O)NR between carbon-carbon atoms of an alkylene group having 2 or more carbon atoms ６ -, -C(=O)-, -NR ６ -, -C(=O)-, -NR６ - or -O- and J １ -C(=O)NR on the end that is not connected ６ -, -C(=O)-, -NR ６ A group having - or -O-, Q ２２ If there are two or more Q ２２ They may be the same or different. Q ２３ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(=O)NR between carbon atoms. ６ -, -C(=O)-, -NR ６ A group having - or -O-, and two Q ２３ They may be the same or different. Q ２４ Q ２４ If the atom at Z to which it is bonded is a carbon atom, then Q ２２ Q ２４ If the atom at Z to which it is bonded is a nitrogen atom, then Q ２３ Q ２４ If there are two or more Q ２４ They may be the same or different. Q ２５ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(=O)NR between carbon atoms. ６ -, -C(=O)-, -NR ６ A group having - or -O-, Q ２５ If there are two or more Q ２５ They may be the same or different. Q ２６ This refers to an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(=O)NR between carbon atoms. ６ -, -C(=O)-, -NR ６ It is a group having - or -O-. Q ２２ Q ２３ Q ２４ Q ２５ Q ２６ If it is an alkylene group, the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6. Z is Q １４ It has a carbon or nitrogen atom that is directly bonded to it, and Q ２４R is a group having a (h1 + h2) valence ring structure with a carbon or nitrogen atom directly bonded to it. ｅ１ is a hydrogen atom or an alkyl group, R ｅ１ If there are two or more, then there are two or more R ｅ１ They may be the same or different. ｅ２ R is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. ｅ３ R is an alkyl group. ６ These are a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

[0143] d1 is an integer between 0 and 3, preferably 1 or 2. d2 is an integer between 0 and 3, preferably 1 or 2. d1 + d2 is an integer between 1 and 3. d3 is an integer between 0 and 3, preferably 0 or 1. d4 is an integer between 0 and 3, preferably 2 or 3. d3 + d4 is an integer between 1 and 3. d1 + d3 is an integer between 1 and 5, preferably 1 or 2. d2 + d4 is an integer between 1 and 5, preferably 4 or 5. e1 + e2 is 3 or 4. e1 is an integer between 1 and 3, preferably 1 or 2. e2 is an integer between 1 and 3, preferably 2 or 3. h1 is an integer of 1 or more, preferably 1 or 2. h2 is an integer of 1 or more, preferably 2 or 3. i1 + i2 is 3 or 4. i1 is an integer between 1 and 3, preferably 1 or 2. i2 is an integer between 1 and 3, preferably 2 or 3. i3 is 2 or 3.

[0144] Q １２ Q １３ Q １４ Q １５ Q ２２ Q ２３ Q ２４ Q ２５ and Q ２６The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6, from the standpoint of ease of manufacturing the compound and superior wear resistance of the surface layer. Examples include 2, 3, 8, 9, and 11. Furthermore, the above number of carbon atoms may also be 1 to 10, 1 to 6, or 1 to 4. However, the lower limit of the number of carbon atoms in the alkylene group when there is a specific bond between carbon atoms is 2.

[0145] The ring structure in Z is the ring structure described above, and the preferred form is also the same. Note that the ring structure in Z is Q １４ Ya Q ２４ Because they bond directly, for example, an alkylene group is linked to the ring structure, and Q is attached to that alkylene group. １４ Ya Q ２４ They will not be connected.

[0146] R ｅ１ , R ｅ２ or R ｅ３ The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of this compound. ｅ２ The number of carbon atoms in the alkyl group portion of the acyloxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the standpoint of facilitating the production of this compound. For h1, it is preferably 1 to 6, more preferably 1 to 4, even more preferably 1 or 2, and particularly preferably 1, from the standpoint of facilitating the production of this compound and providing superior abrasion resistance of the surface layer. For h2, it is preferably 2 to 6, more preferably 2 to 4, and particularly preferably 2 or 3, from the standpoint of facilitating the production of this compound and providing superior abrasion resistance of the surface layer.

[0147] Q １Other forms include base (g2-8) (where p1 = d1 + d3, n2 = d2 × k3 + d4 × k3), base (g2-9) (where p1 = e1, n2 = e2 × k3), base (g2-10) (where p1 = 1, n2 = 2 × k3), base (g2-11) (where p1 = h1, n2 = h2 × k3), base (g2-12) (where p1 = i1, n2 = i2 × k3), base (g2-13) (where p1 = 1, n2 = k3), or base (g2-14) (where p1 = 1, n2 = i3 × k3).

[0148]

[0149] (-A １ - Q １２ -) ｅ１ C(R) ｅ２ ) ４－ｅ１－ｅ２ (-Q ２２ -G １ ) ｅ２ (g2-9) -A １ - Q １３ -N(-Q) ２３ -G １ ) ２ (g2-10) (-A １ - Q １４ -) ｈ１ Z(-Q) ２４ -G １ ) ｈ２ (g2-11) (-A １ - Q １５ -) ｉ１ Si(R ｅ３ ) ４－ｉ１－ｉ２ (-Q ２５ -G １ ) ｉ２ (g2-12) -A １ - Q ２６ -G １ (g2-13) -A １ - Q １２ -CH(-Q) ２２ -G １ )-Si(R ｅ３ ) ３－ｉ３ (-Q ２５ -G １ ) ｉ３ (g2-14)

[0150] However, in equations (g2-8) to (g2-14), A １ The side is Z １ Combined with G １ J １ It combines with Z. １ A １ If the terminal end that bonds with is an alkylene group, Q １ Z １ The terminal end that bonds with is not an alkylene group. Also, Z １ If it is an organopolysiloxane group, A １ Z １ The terminal end that binds to the other end is not an organopolysiloxane group.

[0151] G １ The following group (g3) is Q １ two or more G １ They may be the same or different. G １ The signs other than are the same as the signs in equations (g2-1) to (g2-7). -Si(R ８ ) ３－ｋ３ (-Q ３ -) ｋ３ (g3) However, in the base (g3), the Si side is Q ２２ Q ２３ Q ２４ Q ２５ and Q ２６ Connect to Q ３ J １ Connect to R. ８ It is an alkyl group. Q ３ This refers to an alkylene group, an alkylene group with 2 or more carbon atoms, with -C(=O)NR between carbon atoms. ６ -, -C(=O)-, -NR ６ - or a group having -O-, or (OSi(R ９ ) ２ ) ｐ -O- and Q is 2 or greater. ３ They may be the same or different. k3 is 2 or 3. R ６ R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. ９is an alkyl group, a phenyl group, or an alkoxy group, and has two R ９ They may be the same or different. p is an integer from 0 to 5, and if p is 2 or greater, then 2 or greater (OSi(R ９ ) ２ ) may be the same or different.

[0152] Q ３ The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and may also be 2 to 10 or 2 to 6, from the standpoint of ease of manufacturing the compound and superior wear resistance of the surface layer. Examples include 2, 3, 8, 9, and 11. Furthermore, the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4. However, the lower limit of the number of carbon atoms in the alkylene group when it has a specific bond between carbon atoms is 2. ８ The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the standpoint of facilitating the production of this compound. ９ The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the standpoint of facilitating the production of this compound. ９ The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2, from the viewpoint of excellent storage stability of the compound. p is preferably 0 or 1.

[0153] Examples of compounds of this disclosure include the following compounds. The following compounds are preferred because they are easy to manufacture industrially, easy to handle, and exhibit superior effects of the present invention. R in the following compounds ｔ [R in equation (1)] １１ - (Q) ｒ１ -Z １ This is similar to the case of [the other case], and the preferred form is also similar.

[0154] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-1) is shown below include the following compounds.

[0155]

[0156] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-1) is shown below include the following compounds.

[0157]

[0158] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-2) is shown below. In the formula below, Ak means an alkyl group (for example, an alkyl group having 1 to 15 carbon atoms).

[0159]

[0160]

[0161] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-2) is shown below include the following compounds.

[0162]

[0163]

[0164] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-3) is shown below include the following compounds.

[0165]

[0166] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-3) is shown below include the following compounds.

[0167]

[0168] Z １ Q１ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-4) is shown below include the following compounds.

[0169]

[0170] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-4) is shown below include the following compounds.

[0171]

[0172] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-5) is shown below include the following compounds.

[0173]

[0174] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-5) is shown below include the following compounds.

[0175]

[0176] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-6) is shown below include the following compounds.

[0177]

[0178] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-6) is shown below include the following compounds.

[0179]

[0180] Z １ Q１ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-7) is shown below include the following compounds.

[0181]

[0182] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-7) is shown below include the following compounds.

[0183]

[0184] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-8) is shown below include the following compounds.

[0185]

[0186] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-8) is shown below include the following compounds.

[0187]

[0188] Q in equation (1) １ Examples of compounds in which the group (g2-9) is shown below include the following compounds.

[0189]

[0190] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-10) is shown below include the following compounds.

[0191]

[0192] Z １ If is an organopolysiloxane group, then Q in formula (1) １Examples of compounds in which the group (g2-10) is shown below include the following compounds.

[0193]

[0194] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula 1 １ Examples of compounds in which the group (g2-11) is shown below include the following compounds.

[0195]

[0196] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-11) is shown below include the following compounds.

[0197]

[0198] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-12) is shown below include the following compounds.

[0199]

[0200] Z １ If is an organopolysiloxane group, then Q in formula (1) １ Examples of compounds in which the group (g2-12) is shown below include the following compounds.

[0201]

[0202] Z １ Q １ When the terminal end that bonds with is an alkylene group, Q in formula (1) １ Examples of compounds in which the group (g2-13) is shown below include the following compounds.

[0203]

[0204] Z １ If is an organopolysiloxane group, then Q in formula (1) １Examples of compounds in which the group (g2-13) is shown below include the following compounds.

[0205]

[0206] Q in equation (1) １ Examples of compounds in which the group (g2-14) is shown below include the following compounds.

[0207]

[0208] Specific examples of this compound include, but are not limited to, the following compounds. In the formula, na is the average value and should be 1 or greater, preferably between 2 and 500, and more preferably between 3 and 100.

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] <Physical Properties of the Compound> The number-average molecular weight (Mn) of this compound is preferably 300 to 10,000, and more preferably 300 to 5,000. If the Mn of this compound is above the lower limit of the above range, the abrasion resistance of the surface layer is better. If the Mn of this compound is below the upper limit of the above range, the viscosity is easier to adjust within an appropriate range, and the solubility is improved, resulting in excellent handling during film formation.

[0221] <Method for producing this compound> The method for producing this compound is not particularly limited, but examples include the following methods 1 and 2.

[0222] (Manufacturing Method 1) Manufacturing Method 1 includes the steps of: (1-1) reacting compound p1 represented by the following formula (p1) with compound p2 represented by the following formula (p2) to obtain compound p3 represented by the following formula (p3); and (1-2) reacting compound p3 with compound t1 having an organopolysiloxane residue and a group containing an unsaturated bond to obtain compound P10 containing a group represented by the following formula (P10) and an organopolysiloxane residue. Compound P10 obtained by Manufacturing Method 1 is an example of the above-mentioned compound.

[0223] Step 1-1 Step 1-1 is a step in which compound p3 is obtained by reacting compound p1 and compound p2.

[0224] Compound p1 is a compound represented by the following formula (p1): SiCl ３ -CH ２ -SiCl ２ H (p1)

[0225] Compound p2 is a compound represented by the following formula (p2): C(Y １０ ) ３ H (p2) In formula (p2), Y １０ Each of these is an independent alkoxy group. １０ A preferred embodiment of the alkoxy group in formula (P) above is Y ２ This is similar to the preferred embodiment when is an alkoxy group.

[0226] Compound p3 is a compound represented by the following formula (p3): Si(Y １０ ) ３ -CH ２ -Si(Y １０ ) ２ H (p3) In formula (p3), Y １０ As stated above.

[0227] The reaction conditions in step 1-1 may be adjusted as appropriate by referring to the description in the Examples section below.

[0228] Step 1-2: Step 1-2 is the process of reacting compound p3 and compound t1 to obtain compound P10.

[0229] Compound p3 is as described in step 1-1 above.

[0230] Compound t1 is a compound having organopolysiloxane residues and groups containing unsaturated bonds. The organopolysiloxane residues contained in compound t1 are the same as those of the compound described above, including preferred embodiments. Examples of groups containing unsaturated bonds in compound t1 include alkenyl groups. The alkenyl group may be linear, branched, or cyclic, with linear being preferred. The group containing the unsaturated bond is preferably a group having a vinyl group at its terminus. Specific examples of compound t1 include those derived from formulas (1) or (2) above, including J. １ It has a structure that excludes J １ Examples include compounds in which the terminal group that reacts is an alkenyl group.

[0231] Compound P10 contains the group P10 and organopolysiloxane residues. -Si(Y １０ ) ２ -CH ２ -Si(Y １０ ) ３ (P10) In formula (P10), Y １０ As stated above, the organopolysiloxane residues in compound P10 are the same as those in compound t1. A specific example of compound P10 is J in formula (1) or formula (2) above. １ One example is a structure in which the base P10 is used.

[0232] The reaction between compound p3 and compound t1 in step 1-2 is preferably carried out in the presence of a catalyst. A specific example of a catalyst is a platinum-based catalyst. Furthermore, the reaction between compound p3 and compound t1 in step 1-2 is preferably carried out in the presence of aniline or pyridine.

[0233] The reaction conditions in step 1-2 may be adjusted as appropriate by referring to the description in the Examples section below.

[0234] (Manufacturing Method 2) Manufacturing Method 2 includes: step 2-1, reacting compound p1 with compound t1 to obtain compound p11 containing a group represented by the following formula (p11) and a polysiloxane residue; and step 2-2, reacting compound p11 with compound p12 represented by the following formula (p12) to obtain compound P20 containing a group represented by the following formula (P20) and an organopolysiloxane residue. Compound P20 obtained by Manufacturing Method 2 is an example of the above-described compound.

[0235] Step 2-1 Step 2-1 is a step in which compound p1 and compound t1 are reacted to obtain compound p11.

[0236] Compound p1 and compound t1 are as described in the section on manufacturing method 1 above.

[0237] Compound p11 is a compound containing a group represented by the following formula (p11) and a polysiloxane residue: -Si(Cl) ２ -CH ２ -Si(Cl) ３ (p11) The organopolysiloxane residues contained in compound p11 are the same as those contained in compound t1. A specific example of compound p11 is J in formula (1) or formula (2) above. １ One example is a structure in which base p11 is used.

[0238] The reaction between compound p1 and compound t1 in step 2-1 is preferably carried out in the presence of a catalyst. A specific example of a catalyst is a platinum-based catalyst.

[0239] The reaction conditions in step 2-1 (e.g., reaction temperature, reaction time, etc.) are not particularly limited and may be set appropriately within the range in which compound p11 can be obtained.

[0240] Step 2-2 Step 2-2 is a step in which compound p11 and compound p12 are reacted to obtain compound P20.

[0241] Compound p11 is as described in step 2-1 above.

[0242] Compound p12 is a compound represented by the following formula (p12): C(Y ２１ ) ３ H (p12) In formula (p22), Y ２１ Each of these is independently a hydrolyzable group. ２１ A preferred embodiment of the hydrolyzable group in formula (P) above is Y ２ This is similar to the preferred embodiment when the group is hydrolyzable.

[0243] Compound P20 contains the group P20 and organopolysiloxane residues. -Si(Y ２１ ) ２ -CH ２ -Si(Y ２１ ) ３ (P20) In formula (P20), Y ２１ As stated above, the organopolysiloxane residues in compound P20 are the same as those in compound t1. A specific example of compound P20 is J in formula (1) or formula (2) above. １ One example is a structure in which the base P20 is used.

[0244] The reaction conditions in step 2-2 (e.g., reaction temperature, reaction time, etc.) are not particularly limited and may be set appropriately within the range in which compound P20 can be obtained.

[0245] [Surface Treatment Agent] The surface treatment agent of the present invention (hereinafter referred to as "this surface treatment agent") contains the compound described above. This surface treatment agent is suitable for applications where it is required that the water-repellent and oil-repellent properties of the surface layer not deteriorate even when repeatedly rubbed with fingers (abrasion resistance), and that fingerprints adhering to the surface layer can be easily removed by wiping (fingerprint removal properties) be maintained for a long period of time, such as components that make up the surface that is touched by fingers on a touch panel, eyeglass lenses, and displays of wearable devices. Furthermore, because this surface treatment agent has excellent slip resistance, it is also suitable for use on glass-coated casings of portable devices such as smartphones and tablet terminals. This surface treatment agent is also suitable for use as an anti-fouling coating agent or a waterproof coating agent.

[0246] This surface treatment agent may further contain a liquid medium. In the following description, this surface treatment agent containing a liquid medium may be referred to as a coating solution. The coating solution may be a liquid, a solution, or a dispersion. The coating solution may contain the compound and may contain impurities such as by-products generated in the manufacturing process of the compound. The concentration of the compound in the coating solution is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, even more preferably 0.1 to 10% by mass, and particularly preferably 0.1 to 1% by mass.

[0247] As the liquid medium, an organic solvent is preferred. The organic solvent may be a fluorine-containing organic solvent, a non-fluorine-containing organic solvent, or a mixture of both. Specific examples of fluorine-containing organic solvents include fluorinated alkanes, fluorinated aromatic compounds, fluoroalkyl ethers, fluorinated alkylamines, fluoroalcohols, and hydrofluoroolefins (HFOs). As fluorinated alkanes, compounds having 4 to 8 carbon atoms are preferred. Specific examples of commercially available products include C ６ F １３ H (AGC Corporation, Asahi Clean® AC-2000), C ６ F １３ C ２ H ５ (Manufactured by AGC Corporation, Asahi Clean® AC-6000), C ２ F ５ CHFCHFCF ３ (Chemours Bartrell® XF) is one example. Specific examples of fluorinated aromatic compounds include hexafluorobenzene, trifluoromethylbenzene, perfluorotoluene, and bis(trifluoromethyl)benzene. As for fluoroalkyl ethers, compounds with 4 to 12 carbon atoms are preferred. A specific example of a commercially available product is CF ３ CH ２ OCF ２ CF ２ H (manufactured by AGC Corporation, Asahi Clean® AE-3000), C ４ F ９ OCH ３ (Manufactured by 3M, Novec® 7100), C４ F ９ OC ２ H ５ (Manufactured by 3M, Novec® 7200), C ２ F ５ CF(OCH) ３ ) C ３ F ７ (Novec® 7300, manufactured by 3M) is one example. Specific examples of fluorinated alkylamines include perfluorotripropylamine and perfluorotributylamine. Specific examples of fluoroalcohols include 2,2,3,3-tetrafluoropropanol, 2,2,2-trifluoroethanol, and hexafluoroisopropanol. Specific examples of HFOs include 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (Amorea® AS-300, manufactured by AGC). Non-fluorinated organic solvents are preferably compounds consisting only of hydrogen atoms and carbon atoms, or compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms, and include hydrocarbon organic solvents, alcoholic organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, and glycol organic solvents.

[0248] Specific examples of hydrocarbon organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexyl, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.

[0249] 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.

[0250] 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, and 3,3,5-trimethylcyclohexanone and isophorone.

[0251] Specific examples of ether-based organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.

[0252] 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, and ethylene glycol monoethyl ether acetate. Examples include tate, ethylene glycol 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, 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.

[0253] 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.

[0254] Other organic solvents include chlorinated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds.

[0255] Specific examples of chlorinated organic solvents include dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0256] Specific examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0257] Specific examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0258] Specific examples of siloxane compounds include hexamethyldisiloxane, octamethyltrisiloxane, and decamethyltetrasiloxane.

[0259] The coating liquid preferably contains 60 to 99.999% by mass of the liquid medium, more preferably 80 to 99.99% by mass, even more preferably 90 to 99.9% by mass, and particularly preferably 99 to 99.9% by mass.

[0260] The surface treatment agent may contain other components besides the compound and the liquid medium, to the extent that they do not impair the effects of the disclosure. Examples of other components include known additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation reaction of hydrolyzable silyl groups. The content of other components in the surface treatment agent is preferably 10% by mass or less, and more preferably 1% by mass or less.

[0261] The total concentration of the main compound and other components in the coating solution (hereinafter referred to as "solid content concentration") is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, even more preferably 0.01 to 10% by mass, and particularly preferably 0.01 to 1% by mass. The solid content concentration of the coating solution is calculated from the mass of the coating solution before heating and the mass after heating in a convection dryer at 120°C for 4 hours.

[0262] [Article] The article of the present invention (hereinafter referred to as "the Article") has a surface layer formed from the Compound or the Surface Treatment Agent on the surface of a substrate. An example of the Article will be described with reference to the drawings. Figure 1 is a schematic cross-sectional view showing a first article, which is an example of the Article. The first article is an article 20 having a substrate 12, a base layer 14, and a surface layer 22 in that order, wherein the base layer 14 contains an oxide containing silicon, and the surface layer 22 contains a condensate of the Compound.

[0263] The material and shape of the base material 12 may be appropriately selected according to the intended use of the article 20. Examples of materials for the base material 12 include glass, resin, sapphire, metal, ceramic, stone, and composite materials thereof. The glass may be chemically strengthened. Examples of base materials 12 that require water-repellent and oil-repellent properties include base materials for touch panels, base materials for displays, and base materials that constitute the housing of electronic devices. The base materials for touch panels and display substrates are translucent. "Translucent" means that the normal incidence visible light transmittance in accordance with JIS R3106:1998 (ISO 9050:1990) is 25% or more. Glass or transparent resin is preferred as the material for the base material for touch panels.

[0264] The substrate 12 may have surface treatments such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment applied to the surface on which the underlayer 14 is provided. Surface treatment further improves the adhesion between the substrate 12 and the underlayer 14, and as a result, the abrasion resistance of the surface layer 22 is further improved. As for the surface treatment, corona discharge treatment or plasma treatment is preferred because it further improves the abrasion resistance of the surface layer 22.

[0265] The base layer 14 is a layer containing an oxide that includes at least silicon, and may also contain other elements. By including silanol groups on the surface of the base layer 14, the hydrolyzable silyl groups of the compound undergo dehydration condensation, forming Si-O-Si bonds between it and the base layer 14, resulting in a surface layer 22 with superior abrasion resistance.

[0266] The silicon dioxide content in the base layer 14 is preferably 65% ​​by mass or more, more preferably 80% by mass or more, even more preferably 85% by mass or more, and particularly preferably 90% by mass or more. If the silicon dioxide content is above the lower limit of the above range, sufficient Si-O-Si bonds are formed in the base layer 14, and the mechanical properties of the base layer 14 are sufficiently ensured. The silicon dioxide content is the remainder obtained by subtracting the total content of other elements (or the sum of the amounts converted to oxides in the case of oxides) from the mass of the base layer 14.

[0267] From the standpoint of excellent wear resistance of the surface layer 22, it is preferable that the oxide in the base layer 14 further contains one or more elements selected from alkali metal elements, alkaline earth metal elements, platinum group elements, boron, aluminum, phosphorus, titanium, zirconium, iron, nickel, chromium, molybdenum, and tungsten. The inclusion of these elements strengthens the bond between the base layer 14 and the compound, improving wear resistance.

[0268] When the base layer 14 contains one or more elements selected from iron, nickel, and chromium, the total content of these elements is preferably 10 to 1,100 ppm by mass, more preferably 50 to 1,100 ppm by mass, even more preferably 50 to 500 ppm by mass, and particularly preferably 50 to 250 ppm by mass, relative to silicon oxide. When the base layer 14 contains one or more elements selected from aluminum and zirconium, the total content of these elements is preferably 10 to 2,500 ppm by mass, more preferably 15 to 2,000 ppm by mass, and even more preferably 20 to 1,000 ppm by mass. When the base layer 14 contains alkali metal elements, the total content of these elements is preferably 0.05 to 15% by mass, more preferably 0.1 to 13% by mass, and even more preferably 1.0 to 10% by mass. Examples of alkali metal elements include lithium, sodium, potassium, rubidium, and cesium. When the base layer 14 contains platinum group elements, the total content of these elements is preferably 0.02 to 800 ppm by mass, more preferably 0.04 to 600 ppm by mass, and even more preferably 0.7 to 200 ppm by mass. Examples of platinum group elements include platinum, rhodium, ruthenium, palladium, osmium, and iridium. When the base layer 14 contains one or more elements selected from boron and phosphorus, the total content of these elements is preferably 0.003 to 9, more preferably 0.003 to 2, and even more preferably 0.003 to 0.5, as a ratio of the molar concentration of the total of boron and phosphorus to the molar concentration of silicon, from the viewpoint of excellent wear resistance of the surface layer 22. When the base layer 14 contains alkaline earth metal elements, the total content of these elements is preferably 0.005 to 5, more preferably 0.005 to 2, and even more preferably 0.007 to 2, as a ratio of the molar concentration of the total alkaline earth metal elements to the molar concentration of silicon, from the viewpoint of excellent wear resistance of the surface layer 22. Examples of alkaline earth metal elements include calcium, strontium, barium, and magnesium.

[0269] To improve the adhesion of this surface treatment agent and to improve the water-repellent, oil-repellent, and abrasion-resistant properties of article 20, the base layer 14 is preferably a silicon oxide layer containing alkali metal atoms. In the silicon oxide layer, the average concentration of alkali metal atoms in the region at a depth of 0.1 to 0.3 nm from the surface in contact with the surface layer 22 is 2.0 × 10⁻¹⁶. １９ atoms / cm ３ The above is preferable. On the other hand, in order to ensure sufficient mechanical properties of the silicon oxide layer, the average concentration of alkali metal atoms is 4.0 × 10 ２２ atoms / cm ３ The following is preferable:

[0270] The thickness of the base layer 14 is preferably 1 to 200 nm, and more preferably 2 to 20 nm. If the thickness of the base layer 14 is above the lower limit of the above range, the adhesive improvement effect of the base layer 14 is easily obtained. If the thickness of the base layer 14 is below the upper limit of the above range, the abrasion resistance of the base layer 14 itself is increased. Methods for measuring the thickness of the base layer 14 include cross-sectional observation of the base layer 14 using an electron microscope (SEM, TEM, etc.), and methods using an optical interferometer, spectroscopic ellipsometer, step meter, etc.

[0271] A specific example of a method for forming the underlayer 14 is a method of depositing a vapor deposition material having the desired composition of the underlayer 14 onto the surface of the substrate 12. An example of a vapor deposition method is the vacuum vapor deposition method. The vacuum vapor deposition method is a method of evaporating the vapor deposition material in a vacuum chamber and depositing it onto the surface of the substrate 12. The temperature during vapor deposition (for example, the temperature of the boat on which the vapor deposition material is placed when using a vacuum vapor deposition apparatus) is preferably 100 to 3,000°C, and more preferably 500 to 3,000°C. The pressure during deposition (for example, when using a vacuum deposition apparatus, the absolute pressure in the tank where the deposition material is placed is preferably 1 Pa or less, and more preferably 0.1 Pa or less.) is important. When forming the underlayer 14 using the deposition material, one deposition material may be used, or two or more deposition materials containing different elements may be used. Methods for evaporating the deposition material include resistance heating, in which the deposition material is melted and evaporated on a resistance heating boat made of a high-melting-point metal, and electron gun method, in which an electron beam is irradiated onto the deposition material to directly heat the material, melt the surface, and evaporate it. The electron gun method is preferred as an evaporation method for the deposition material because it can heat locally, allowing for the evaporation of high-melting-point substances, and because areas not exposed to the electron beam are at low temperatures, eliminating the risk of reaction with the container or contamination with impurities. As the deposition material used in the electron gun method, molten granules or sintered bodies are preferred because they are less likely to scatter even if an airflow is generated.

[0272] The surface layer 22 on the base layer 14 contains a condensate of the compound. The condensate of the compound includes a compound in which hydrolyzable silyl groups in the compound undergo hydrolysis to form silanol groups (Si-OH), and these silanol groups undergo intermolecular condensation to form Si-O-Si bonds, and a compound in which silanol groups in the compound undergo condensation with silanol groups or Si-OM groups (where M is an alkali metal element) on the surface of the base layer 14 to form Si-O-Si bonds. The surface layer 22 may also contain condensates of compounds other than the compound contained in the surface treatment agent. The surface layer 22 may contain a compound having hydrolyzable silyl groups in a state in which some or all of the hydrolyzable silyl groups of the compound have undergone condensation.

[0273] The thickness of the surface layer 22 is preferably 1 to 100 nm, and more preferably 1 to 50 nm. If the thickness of the surface layer 22 is above the lower limit of the above range, the effect of the surface layer 22 can be sufficiently obtained. If the thickness of the surface layer 22 is below the upper limit of the above range, the utilization efficiency is high. The thickness of the surface layer 22 is the thickness obtained by an X-ray diffractometer for thin film analysis. The thickness of the surface layer 22 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.

[0274] Another example of an article of the present invention is a second article. The second article is an article 20 having a substrate 10 with a base layer and a surface layer 22 in that order, wherein the substrate 10 with the base layer contains a silicon-containing oxide and the surface layer 22 contains a condensate of the compound.

[0275] In the second article, since the substrate 10 with the underlayer has the same composition as the underlayer 14 in the first article, the surface layer 22 has excellent abrasion resistance even when the surface layer 22 is directly formed on the substrate 10 with the underlayer. The material of the substrate 10 with the underlayer in the second article can be any material having the same composition as the underlayer 14, for example, a glass substrate. Details of the material of the substrate 10 with the underlayer are the same as those of the substrate 12 and the underlayer 14, so the explanation is omitted here. Also, the composition of the surface layer 22 is the same as that of the first article, so the explanation is omitted here.

[0276] Specific examples of articles of the present invention include optical components, touch panels, anti-reflective films, anti-reflective glass, and SiO2 used as parts of the following products. ２ Examples include processed glass, tempered glass, sapphire glass, quartz substrates, and mold metals. Products include: car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio systems, gaming devices, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (endoscopes, etc.), photocopiers, personal computers (PCs), liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc.

[0277] [Method for Manufacturing Articles] The method for manufacturing articles of the present invention is to form a surface layer using the compound or the surface treatment agent by a dry coating method or a wet coating method.

[0278] This compound and surface treatment agent can be used directly in dry coating methods and are suitable for forming a surface layer with excellent adhesion by dry coating. Examples of dry coating methods include vacuum deposition, CVD, and sputtering. Vacuum deposition is preferable in terms of suppressing the decomposition of this surface treatment agent and the simplicity of the equipment. For vacuum deposition, a pellet-like material in which this compound is supported on a porous metal body made of a metal material such as iron or steel may be used. The pellet-like material on which this compound is supported can be manufactured by impregnating a porous metal body with a solution containing this compound and drying it to remove the liquid medium.

[0279] This surface treatment agent (coating solution) containing a liquid medium can be suitably used in wet coating methods. Examples of wet coating methods 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.

[0280] To improve the abrasion resistance of the surface layer, operations to promote the reaction between the compound and the substrate may be performed as needed. Such operations include heating, humidification, and light irradiation. For example, heating a substrate with a surface layer formed in a humid atmosphere can promote reactions such as the hydrolysis of hydrolyzable groups, the reaction between hydroxyl groups on the substrate surface and silanol groups, and the formation of siloxane bonds through the condensation reaction of silanol groups. After surface treatment, compounds in the surface layer that are not chemically bonded to other compounds or the substrate may be removed as needed. Specific methods include, for example, pouring a solvent onto the surface layer or wiping it with a cloth soaked in a solvent.

[0281] The present invention will be described in detail below with reference to examples. Of Examples 1 to 11, Examples 1 to 10 are examples, and Example 11 is a comparative example. However, the present invention is not limited to these examples.

[0282] [Example 1] <Synthesis of Compound A> 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 (tetrahydrofuran, 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 under reduced pressure. The obtained crude solution was subjected to flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate) to obtain 8.3 g of Compound A. The structure of Compound A was confirmed from the following NMR data. The structures of each compound described later were also confirmed in the same way using NMR data.

[0283]

[0284] (NMR data of compound A) 1 H -NMR (400 MHz, CDCl3) δ 2.41 (q, J = 7.2 Hz, 1H), 0.20 - -0.21 (m, 21H).

[0285] <Synthesis of Compound B> Compound A (2.0 g) was added to THF (20 g), cooled to 0°C, and then a methyllithium diethoxymethane solution (3.1 M) (2.7 mL) was added and the mixture was stirred for 10 minutes. Next, a solution of hexamethylcyclotrisiloxane (5.6 g) dissolved in THF (20 g) was added and the mixture was stirred at 25°C for 4 hours. Next, chlorodimethylsilane (2.0 g) was added and the mixture was stirred at 25°C for 1 hour. After extraction with hexane and water, low-boiling point components were removed by distillation under reduced pressure. The obtained crude solution was subjected to flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) to obtain 4.3 g of compound B. The average value of na in compound B was 9.

[0286]

[0287] (NMR data of compound B) 1 H NMR (400 MHz, CDCl3) δ 4.63 (p, J = 2.8Hz, 1H), 0.11 (d, J = 2.8 Hz, 6H), 0.09 - -0.12 (m, 75H).

[0288] <Synthesis of Compound C> Compound B (2.3 g) was mixed with dichloromethane (20 g) and 18-bromo-1-octadecene (0.75 g) and stirred 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, 1.8 g of compound C was obtained by flash column chromatography using silica gel (developing solvent: hexane / dichloromethane). The average value of na in compound C was 9.

[0289]

[0290] (NMR data of compound C) 1 H NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.89 - 1.83 (m, 2H), 1.40- 1.24 (m, 30H), 0.54 - 0.50 (m, 2H), 0.09 - 0.01 (m, 81H).

[0291] <Synthesis of Compound D> Compound C (1.8 g) was mixed with THF (20 g), a THF solution of allyl magnesium chloride (2.0 M) (20 mL), and copper(II) chloride (0.02 g), and the mixture was stirred at 50°C for 2 hours. Hydrochloric acid and hexane were added for extraction, and the low-boiling point components were removed by distillation under reduced pressure. The resulting sludge was subjected to flash column chromatography using silica gel (developing solvent: hexane / dichloromethane) to obtain 1.5 g of compound D. The average value of na in compound D was 9. The structure of compound D was confirmed from the following NMR data.

[0292]

[0293] (NMR data of compound D) 1 H NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.07 - 2.01 (m, 2H), 1.39 - 1.23 (m, 34H), 0.54 - 0.50 (m, 2H), 0.10 - 0.01 (m, 81H).

[0294] <Synthesis of Compound X> Under a nitrogen atmosphere, 5.0 g of 1,1,1,3,3-pentachloro-1,3-disilapropane, synthesized by the method described in Chem. Eur. J. 2014, 20, 9442, was added to trimethyl orthoformate (9.1 g) and stirred at 100°C for 6 hours. Subsequently, another 9.1 g of trimethyl orthoformate was added and stirred at 120°C for 15 hours. After the reaction, volatile compounds were removed by distillation under reduced pressure to obtain 3.5 g of a mixture containing compound X (1,1,1,3,3-pentamethoxy-1,3-disilapropane). NMR analysis revealed that the content of compound X was 60% by mass.

[0295]

[0296] <Synthesis of Compound 1A> Compound D (0.40 g) was dissolved in dichloromethane (1.0 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.3 mg) and compound X (60% by mass, 0.20 g) were added, and the mixture was stirred at 25°C for 16 hours. By distilling off the volatile compounds under reduced pressure at 60°C, 0.60 g of compound 1A was obtained. The average value of na in compound 1A was 9.

[0297]

[0298] (NMR data of compound 1A) 1H-NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.42 - 1.26 (m, 38H), 0.70 - 0.64 (m, 2H), 0.54 - 0.50 (m, 2H), 0.10 - 0.03 (m, 83H).

[0299] [Example 2] <Synthesis of Compound E> 1,1,1,3,3,5,5,7,7-nonamethyltetrasiloxane (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 E was obtained by flash column chromatography using silica gel (developing solvent: decane / dichloromethane).

[0300]

[0301] (NMR data of compound E) 1 H NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.89 - 1.82 (m, 2H), 1.44 - 1.25 (m, 30H), 0.55 - 0.51 (m, 2H), 0.10 - 0.02 (m, 27H).

[0302] <Synthesis of Compound F> 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 E (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 F was obtained by flash column chromatography using silica gel (developing solvent: decane).

[0303]

[0304] (NMR data of compound F) 1 H NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.06 - 2.01 (m, 2H), 1.43 - 1.25 (m, 50H), 0.55 - 0.51 (m, 2H), 0.09 - 0.04 (m, 27H).

[0305] <Synthesis of Compound 1B> Compound F (0.60 g) was dissolved in dichloromethane (1.0 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 5.5 mg) and compound X (60% by mass, 0.43 g) were added, and the mixture was stirred at 25°C for 16 hours. Low-boiling point components were removed by distillation under reduced pressure. The resulting crude solution was subjected to flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate) to obtain 0.32 g of compound 1B.

[0306]

[0307] (NMR data of compound 1B) 1 H NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.36 - 1.20 (m, 54H), 0.76 - 0.63 (m, 2H), 0.55 - 0.51 (m, 2H), 0.15 - 0.01 (m, 27H), -0.03 (s, 2H).

[0308] [Example 3] <Synthesis of Compound G> 10 g of 18-bromo-1-octadecene was mixed with 10 g of dichloromethane, 15 g of 1,1,1,3,3-pentamethyldisiloxane, 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, 12 g of compound G was obtained by flash column chromatography using silica gel (developing solvent: hexane / dichloromethane).

[0309]

[0310] (NMR data of compound G) 1 H NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.89 - 1.82 (m, 2H), 1.49 - 1.25 (m, 30H), 0.52 - 0.48 (m, 2H), 0.06 (s, 9H), 0.03 (s, 6H).

[0311] <Synthesis of Compound H> 18-bromo-1-octadecene (2.0 g) was mixed with THF (5 g) and magnesium (0.17 g) and stirred at 60°C for 1 hour. This solution was added to a solution of compound G (2.1 g) mixed with THF (5.0 g), copper(II) chloride (6.2 mg), and 1-phenyl-1-1-propyne (0.53 g) and stirred at 0°C for 1 hour. Then stirred at 25°C for 17 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were removed by distillation under reduced pressure. Finally, compound H (0.67 g) was obtained by flash column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane).

[0312]

[0313] (NMR data of compound H) 1 H NMR (400 MHz, CDCl3) δ 5.80 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.07 - 2.01 (m, 2H), 1.43 - 1.25 (m, 64H), 0.52 - 0.48 (m, 2H), 0.06 (s, 9H), 0.03 (s, 6H).

[0314] <Synthesis of Compound 1C> Compound H (0.45 g) dissolved in dichloromethane (1.0 g) was mixed with a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 18 mg) and compound X (60% by mass, 0.70 g), and the mixture was stirred at 25°C for 17 hours. After removing the low-boiling point components under reduced pressure, compound 1C (0.20 g) was obtained by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate).

[0315]

[0316] (NMR data of compound 1C) 1 H NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.52 (s, 6H), 1.45 - 1.20 (m, 68H), 0.76 - 0.62 (m, 2H), 0.52 - 0.48 (m, 2H), 0.06 (s, 9H), 0.03 (s, 6H), -0.03 (s, 2H).

[0317] [Example 4] <Synthesis of Compound J> Compound J was obtained by following the same procedure as in the synthesis of Compound D, except that Compound E (1.5 g) was used instead of Compound C.

[0318]

[0319] (NMR data of compound J) 1 H NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 - 4.92 (m, 2H), 2.06 - 2.00 (m, 2H), 1.43 - 1.24 (m, 34H), 0.55 - 0.51 (m, 2H), 0.09 - 0.04 (m, 27H).

[0320] <Synthesis of Compound 1D> Compound 1D was obtained in 900 mg using the same procedure as in the synthesis of Compound 1B, except that Compound J (1.3 g) was used instead of Compound F.

[0321]

[0322] (NMR data of compound 1D) 1 H NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.36 - 1.20 (m, 32H), 0.76 - 0.63 (m, 2H), 0.55 - 0.51 (m, 2H), 0.10 - 0.04 (m, 27H), -0.03 (s, 2H).

[0323] [Example 5] <Synthesis of Compound K> Compound K was obtained by the same procedure as in the synthesis of Compound E, except that 1,1,1,3,3,5,5,7,7-nonamethyltetrasiloxane was replaced with 1,1,1,3,3,5,5,7,7,9,9,11,11,13,13,15,15-heptadecamethyloctasiloxane (2.0 g).

[0324]

[0325] (NMR data of compound K) 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), 0.54 - 0.50 (m, 2H), 0.09 - 0.04 (m, 51H).

[0326] <Synthesis of Compound L> Compound L was obtained in 900 mg using the same procedure as in the synthesis of Compound D, except that Compound K (1.0 g) was used instead of Compound C.

[0327]

[0328] (NMR data of compound L) 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, 34H), 0.54 - 0.50 (m, 2H), 0.09 - 0.04 (m, 51H).

[0329] <Synthesis of Compound 1E> Compound 1E was obtained in 630 mg using the same procedure as in the synthesis of Compound 1B, except that Compound L (900 mg) was used instead of Compound F.

[0330]

[0331] (NMR data of compound 1E) 1 H NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.36 - 1.20 (m, 32H), 0.76 - 0.63 (m, 2H), 0.54 - 0.50 (m, 2H), 0.09 - 0.04 (m, 51H), -0.03 (s, 2H).

[0332] [Example 6] <Synthesis of Compound M> Compound L was obtained by the same procedure as in the synthesis of Compound F, except that Compound C (2.0 g) was used instead of Compound E. The average value of na in Compound M was 9.

[0333] (NMR data of compound M) 1 H-NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.08 - 2.01 (m, 2H), 1.42 - 1.23 (m, 50H), 0.54 - 0.50 (m, 2H), 0.10 - 0.01 (m, 81H).

[0334]

[0335] <Synthesis of Compound 1F> Compound 1F was obtained in 830 mg using the same procedure as the synthesis of Compound 1B, except that Compound M (1.6 g) was used instead of Compound F. The average value of na in Compound 1F was 9.

[0336] (NMR data of compound 1F) 1H-NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.42 - 1.26 (m, 54H), 0.70 - 0.64 (m, 2H), 0.54 - 0.50 (m, 2H), 0.10 - 0.03 (m, 83H).

[0337]

[0338] [Example 7] <Synthesis of Compound N> Compound N was obtained by following the same procedure as in the synthesis of Compound F, except that Compound C (2.0 g) was used instead of Compound E, and 18-Bromo-1-Octadecene (1.4 g) was used instead of 11-Bromo-1-Undecene. The average value of na in Compound N was 7.

[0339] (NMR data of compound N) 1 H-NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.08 - 2.01 (m, 2H), 1.42 - 1.21 (m, 64H), 0.54 - 0.50 (m, 2H), 0.10 - 0.01 (m, 69H).

[0340]

[0341] <Synthesis of Compound 1G> Compound 1G was obtained in 400 mg using the same procedure as in the synthesis of Compound 1B, except that Compound N (820 mg) was used instead of Compound F. The average value of na in Compound 1G was 7.

[0342] (NMR data of compound 1G) 1 H-NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.42 - 1.26 (m, 68H), 0.70 - 0.64 (m, 2H), 0.54 - 0.50 (m, 2H), 0.10 - -0.03 (m, 71H).

[0343]

[0344] [Example 8] <Synthesis of Compound O> Compound (25) described in International Publication No. 2024 / 034669 was used as Compound O.

[0345]

[0346] <Synthesis of Compound 1H> Compound O (1.0 g) was dissolved in dichloromethane (3.0 g). Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 37 mg) and compound X (60% by mass, 1.7 g) were added, and the mixture was stirred at 25°C for 16 hours. By distilling off the volatile compounds under reduced pressure at 60°C, 1.6 g of compound 1H was obtained.

[0347] (NMR data of compound 1H) 1 H-NMR (400 MHz, CDCl3) δ 5.50 (brs, 1H), 3.57 (s, 18H), 3.53 (s, 12H), 3.18 (t, J = 6.0 Hz, 2H), 2.17 - 2.13 (m, 2H), 1.64 - 1.25 (m, 49H), 0.72 - 0.65 (m, 4H), 0.46 - 0.42 (m, 2H), 0.09 - -0.01 (m, 25H).

[0348]

[0349] [Example 9] <Synthesis of Compound P> Compound P was obtained according to the synthesis method described in Japanese Patent Application Publication No. 2014-15587. The average value of na in compound P was 6.

[0350]

[0351] <Synthesis of Compound Q> Compound P (1.0 g) was mixed with dichloromethane (5.0 g) and 18-bromo-1-octadecene (2.1 g) and stirred until homogeneous. Next, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 40 mg) was added and stirred at 25°C for 2 hours. After removing the low-boiling components under reduced pressure, 1.7 g of compound Q was obtained by flash column chromatography using silica gel (developing solvent: hexane / dichloromethane). The average value of na in compound Q was 6.

[0352] (NMR data of compound Q) 1 H NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 4H), 1.89 - 1.82 (m, 4H), 1.49 - 1.25 (m, 60H), 0.54 - 0.50 (m, 4H), 0.10 - 0.02 (m, 48H).

[0353]

[0354] <Synthesis of Compound R> Compound R was obtained by the same procedure as the synthesis of Compound D, except that Compound Q (1.7 g) was used instead of Compound C. The average value of na in Compound R was 6.

[0355] (NMR data of compound R) 1 H NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 2H), 5.02 - 4.91 (m, 4H), 2.07 - 2.01 (m, 4H), 1.39 - 1.23 (m, 68H), 0.54 - 0.50 (m, 4H), 0.10 - 0.02 (m, 48H).

[0356]

[0357] <Synthesis of Compound 1I> Compound 1I was obtained by the same procedure as in the synthesis of Compound 1H, except that Compound R (1.5 g) was used instead of Compound O. The average value of na in Compound 1I was 6.

[0358] (NMR data of compound 1I) 1 H-NMR (400 MHz, CDCl3) δ 3.57 (s, 18H), 3.53 (s, 12H), 1.42 - 1.26 (m, 76H), 0.70 - 0.64 (m, 4H), 0.54 - 0.50 (m, 4H), 0.10 - -0.03 (m, 52H).

[0359]

[0360] [Example 10] <Synthesis of Compound S> Compound S was obtained by following the same procedure as in the synthesis of Compound F, except that Compound K (2.0 g) was used instead of Compound E, and 18-Bromo-1-Octadecene (1.5 g) was used instead of 11-Bromo-1-Undecene.

[0361]

[0362] (NMR data of compound S) 1 H NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.08 - 2.01 (m, 2H), 1.42 - 1.23 (m, 64H), 0.54 - 0.50 (m, 2H), 0.09 - 0.00 (m, 51H).

[0363] <Synthesis of Compound 1J> Compound 1J was obtained in 720 mg using the same procedure as in the synthesis of Compound 1B, except that Compound S (1.2 g) was used instead of Compound F.

[0364]

[0365] (NMR data of compound 1J) 1 H-NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.42 - 1.26 (m, 68H), 0.70 - 0.64 (m, 2H), 0.54 - 0.50 (m, 2H), 0.10 - -0.03 (m, 53H).

[0366] [Example 11] Compound (26) described in International Publication No. 2024 / 034669 was designated as compound H1.

[0367]

[0368] [Manufacturing of Articles] 30 g of silicon oxide was placed as a deposition source in the copper hearth inside a vacuum deposition apparatus (VTR-350M, manufactured by ULVAC, Inc.). A glass substrate was placed inside the vacuum deposition apparatus, and the inside of the vacuum deposition apparatus was 5 × 10 －３ The chamber was evacuated until the pressure was below Pa. The hearth was heated to approximately 2,000°C, and silicon dioxide was vacuum-deposited onto the surface of the substrate to prepare a substrate with a silicon dioxide layer approximately 20 nm thick. The substrate with the silicon dioxide layer was placed on the sample stage of a spray coater (API-90RS, manufactured by Apiros Co., Ltd.) with the silicon dioxide layer facing the surface. Next, 13 g of a heptane solution containing 0.2% by mass of the compound obtained in each example was put into a syringe in the spray coater and spray-coated at an atomization pressure of 130 kPa, a nozzle-to-sample surface distance of 50 mm, and a scanning speed of 300 mm / second (wet coating method). Subsequently, the substrate with the silicon dioxide layer coated on the surface was heat-treated at 140°C for 30 minutes to obtain an evaluation sample (article) in which the substrate, silicon dioxide layer, and surface layer were stacked in this order.

[0369] [Evaluation] The following evaluations were conducted using the obtained items. The results of the evaluation tests are shown in Table 1.

[0370] <Oleic Acid Repellency> Approximately 2 μL of oleic acid was dropped onto the surface layer of an object, and the initial oil contact angle (oleic acid contact angle) was measured using a contact angle measuring device (product name "DM-500", manufactured by Kyowa Interface Science Co., Ltd.). Measurements were taken at five locations on the surface layer, and the average value was calculated to evaluate the oil repellency of the surface layer. The 2θ method was used to calculate the oil contact angle. The evaluation criteria are as follows: A: Average oleic acid contact angle is 53 degrees or higher. B: Average oleic acid contact angle is 45 degrees or higher and less than 53 degrees. C: Average oleic acid contact angle is less than 45 degrees.

[0371] <Abrasion Resistance> For the surface layer of the article, in accordance with JIS L0849:2013 (corresponding ISO: 105-X12:2001), a reciprocating traverse test machine (manufactured by KNT Co., Ltd.) was used to measure the oleic acid contact angle after the friction test, after every 100 reciprocations of steel wool bonstar (#0000) at a pressure of 98.07 kPa and a speed of 320 cm / min. The method for measuring the oleic acid contact angle after the friction test is as described above. First, after 100 reciprocations, if the obtained oleic acid contact angle value was less than 50 degrees, the friction test was terminated and the number of rubs at the end was recorded. If the obtained oleic acid contact angle value was 50 degrees or more, the friction test was continued. This operation was repeated until the number of rubs reached a maximum of 2000. The evaluation criteria are as follows: (Evaluation Criteria) A: Number of rubs is 1000 or more. B: Number of rubs is 100 or more but less than 1000. C: Less than 100 rubs.

[0372]

[0373] As shown in Table 1, the compounds obtained in Examples 1 to 10 were confirmed to be able to form a surface layer with excellent oil repellency and abrasion resistance.

[0374] Articles having a surface layer formed using this compound include, for example, optical articles, touch panels, anti-reflective films, anti-reflective glass, and SiO2, which are used as parts of the following products. ２ It is useful as processed glass, tempered glass, sapphire glass, quartz substrates, mold metals, etc. Products: Car navigation systems, mobile phones, digital cameras, digital video cameras, personal digital assistants (PDAs), portable audio players, car audio systems, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, medical equipment (endoscopes, etc.), photocopiers, personal computers (PCs), liquid crystal displays, organic EL displays, plasma displays, touch panel displays, protective films, anti-reflective films, anti-reflective glass, nanoimprint templates, molds, etc.

[0375] This application claims priority based on Japanese Patent Application No. 2025-41090, filed on 14 March 2025, and incorporates all of its disclosures herein.

[0376] 10 Substrate with undercoat 12 Substrate 14 Undercoat 20 Article 22 Surface layer

Claims

1. A compound comprising a group represented by the following formula (P) and an organopolysiloxane residue. -{Si(Y １ )(Y ２ )-L} ｍ -{Si(Y １ )(Y ２ )-CH ２}-SiY ３ ３ (P) Provided that, Y １ are each independently a hydrolyzable group or a hydroxyl group, Y ２ are each independently a hydrolyzable group, a hydroxyl group or a hydrocarbon group, Y ３ are each independently a hydrolyzable group, a hydroxyl group or a hydrocarbon group, and at least one of Y ３ is a hydrolyzable group or a hydroxyl group, L is -CH ２ - or an oxygen atom, and m is an integer of 0 or more.

2. The compound according to claim 1, represented by the following formula (1) or the following formula (2). [R １１ - (Q) ｒ１ -Z １ ] ｐ１ - Q １ - (J １ ) ｎ２ (1) (J １ ) ｎ２ - Q ２ -Z ２ - Q ２ - (J １ ) ｎ２ (2) However, J １ Each of these is independently a group represented by the above formula (P), and R １１ Each of these is independently a group containing Si and not having a reactive silyl group, each of these is independently -O- or -OC(=O)-, each of these is independently 0 or 1, Z １ Each of these is independently a single bond, an alkylene group which may have an etheric oxygen atom, an organopolysiloxane group, or a combination of an alkylene group which may have an etheric oxygen atom and an organopolysiloxane group, Z ２ Q is a combination of an organopolysiloxane group, or an alkylene group which may have an etheric oxygen atom, and an organopolysiloxane group. １ is a (p1 + n2) valence linking group, Q ２ Each is independently a (1 + n2) valence linking group, p1 is an integer greater than or equal to 1, and each is independently an integer greater than or equal to 1, and in equation (1), at least one [R １１ - (Q) ｒ１ -Z １ This includes organopolysiloxane residues.

3. The compound according to claim 2, wherein n2 is 1 or 2 in formula (1) and formula (2).

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

5. The surface treatment agent according to claim 4, further comprising a liquid medium.

6. The surface treatment agent according to claim 4, which is an antifouling coating agent or a waterproof coating agent.

7. The surface treatment agent according to claim 5, which is an antifouling coating agent or a waterproof coating agent.

8. An article having a surface layer formed using the compound described in any one of claims 1 to 3 on the surface of a substrate.

9. The article according to claim 8, which is an optical component.

10. The article according to claim 8, wherein the surface layer is provided on the surface of a component that constitutes the surface of a touch panel that is touched by a finger.

11. A method for manufacturing an article, comprising forming a surface layer by a dry coating method using the surface treatment agent described in claim 4.

12. A method for manufacturing an article, comprising forming a surface layer by a dry coating method using the surface treatment agent described in claim 5.

13. A method for manufacturing an article, comprising forming a surface layer by a wet coating method using the surface treatment agent described in claim 5.

14. A method for producing a compound, comprising reacting compound p1 represented by the following formula (p1) with compound p2 represented by the following formula (p2) to obtain compound p3 represented by the following formula (p3), and then reacting compound p3 with compound t1 having a group containing an organopolysiloxane residue and an unsaturated bond to obtain compound P10 containing a group represented by formula (P10) and an organopolysiloxane residue. SiCl ３ -CH ２ -SiCl ２ H (p1) C(Y １０ ) ３ H (p2) However, Y １０ These are each independently alkoxy groups. Si(Y １０ ) ３ -CH ２ -Si(Y １０ ) ２ H (p3) However, Y １０ As stated above, -Si(Y １０ ) ２ -CH ２ -Si(Y １０ ) ３ (P10) However, Y １０ As stated above.

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