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

WO2026191978A1PCT designated stage Publication Date: 2026-09-17AGC INC
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Patent Information

Application Number
PCT/JP2026/009494
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2025-03-14
Filing Date
2026-03-11
Publication Date
2026-09-17

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Abstract

Provided are: a compound capable of forming a surface layer having excellent oil repellency and abrasion resistance; 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 disclosure contains: a group represented by -{Si(Y1)(Y2)-L}m-Si(Y3)3; and a group represented by (RQ)n1-LQ-. Y1 is a hydrolyzable group or the like, Y2 is a hydrolyzable group or the like, Y3 is a hydrolyzable group or the like, at least one Y3 is a hydrolyzable group or the like, L is -(CH2)n- or an oxygen atom, n is an integer of 1 or more, and m is an integer of 1 or more. RQ is -OCF3 or the like, X11 is an alkyl group or the like, X12 is an alkyl group or the like, X13 is an alkyl group or the like, LQ is a single bond or the like, and n1 is an integer of 1 or more.
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Description

Compounds, surface treatment agents, articles, and methods for manufacturing articles

[0001] This disclosure relates to compounds, surface treatment agents, articles, and methods for manufacturing articles.

[0002] In a wide variety of fields, including electrical and electronic materials, semiconductor materials, optical materials, building materials, and automotive parts, methods for forming a surface layer on the surface of a component (substrate) are known for purposes such as suppressing the adhesion of dirt to the component being used. For example, Patent Document 1 describes a method for forming a surface layer on the surface of a substrate using a surface treatment agent containing a fluorine-containing silane compound represented by the following formula.

[0003]

[0004] Japanese Patent Publication No. 2024-114678

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

[0006] This disclosure is made in view of the above-mentioned problems and aims to provide a compound capable of forming a surface layer with excellent oil repellency and abrasion resistance, a surface treatment agent, an article having a surface layer formed from the compound, and a method for manufacturing the article.

[0007] The present inventors have diligently studied the above problems and have found that the above problems can be solved by the following configuration: [1] A compound comprising a group represented by the following formula (P) and a group represented by the following formula (Q). - {Si(Y 1 ) (Y 2 ) - L} m -Si(Y 3 ) 3 (P) However, 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 Y3 At least one is a hydrolyzable group or a hydroxyl group, and L is -(CH 2 ) n - or an oxygen atom; n is an integer of 1 or more, and when m is an integer of 2 or more, a plurality of L may be the same or different from each other; m is an integer of 1 or more. (R Q ) n1 -L Q -  (Q) Provided that R Q is -OCF 3 , -SCF 3 , -SF 4 X 11 , -N(CF 3 )X 12 , -CHF 2 , -CH 2 F, -C 6 F 5 , -C 8 F 7 , -Si(X 13 ) 3 , or -Ge(X 13 ) 3 ; X 11 is an alkyl group or a halogen atom; X 12 is an alkyl group or -CF 3 ; a plurality of X 13 are each independently an alkyl group; L Q is a single bond or a (1+n1)-valent group; n1 is an integer of 1 or more; when there are a plurality of R Q , the plurality of R Q may be the same or different from each other. [2] The compound according to [1], which is represented by formula (1): (R Q ) n1 -L Q -L 1 -L 2 -(J 1 ) n2   (1) Provided that (R Q ) n1 -L Q - is a group represented by the above formula (Q), and L 1 is a single bond, or -O-, -C(=O)-, -C(=O)NX 14-, -C(=O)O-, -NX 14 C(=O)-, -OC(=O)-, -NX 14 C(=O)NX 15 -, -NX 14 C(S)NX 15 -, -NX 14 C(=O)O-, -Si(X 14 ) 2 - A divalent hydrocarbon group which may have at least one group selected from the group consisting of a divalent organopolysiloxane residue and a divalent aromatic heterocycle, and if the divalent hydrocarbon group includes a cyclic hydrocarbon group, the cyclic hydrocarbon group may have substituents, X 14 and X 15 Each is independently a hydrogen atom or an alkyl group, L 2 is a single bond or a group with three or more (1+n2) valencies, J 1 is a base represented by the above formula (P), where n2 is an integer greater than or equal to 1, and when n2 is 1, L 2 It is a single bond, J 1 If there are multiple J 1 [1] The compounds in formula (1) above, wherein n2 is 1 or 2. [2] A surface treatment agent comprising the compound in any of [1] to [3]. [3] A surface treatment agent further comprising a liquid medium. [4] A surface treatment agent according to [4] or [5] that is an antifouling coating agent or a waterproof coating agent. [5] An article having a surface layer formed using the compound in any of [1] to [3] on the surface of a substrate. [6] An article according to [7] that is an optical member. [7] An article according to [7] or [8] having the above surface layer on the surface of a member 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 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 of [4] to [6].

[0008] According to this disclosure, it is possible to provide a compound capable of forming a surface layer with excellent oil-repellent and abrasion-resistant properties, a surface treatment agent, an article having a surface layer formed from the compound, and a method for manufacturing the article.

[0009] This is a schematic cross-sectional view showing an example of an article in this disclosure.

[0010] The meanings of the terms used in this disclosure are as follows: "Organic group" means a hydrocarbon group which may have substituents and which may have heteroatoms or other bonds in its carbon chain. "Hydrogen group" means 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" means 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. In addition, if identical symbols exist within 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 and "Et" may represent an ethyl group.

[0011] [Compound] The compound according to this embodiment (hereinafter referred to as "this compound") comprises a group represented by the following formula (P) (hereinafter referred to as "group P") and a group represented by the following formula (Q) (hereinafter referred to as "group Q").

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

[0013] In Formula (P), Y 1 are each independently a hydrolyzable group or a hydroxyl group, and Y 2 are each independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and Y 3 are each independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and at least one Y 3 of Y is a hydrolyzable group or a hydroxyl group, L is -(CH 2 ) n - or an oxygen atom, n is an integer of 1 or more, and when m is an integer of 2 or more, a plurality of L may be the same as or different from each other, and m is an integer of 1 or more.

[0014] (R Q ) n1 -L Q - (Q)

[0015] In Formula (Q), R Q is -OCF 3 , -SCF 3 , -SF 4 X 11 , -N(CF 3 )X 12 , -CHF 2 , -CH 2 F, -C 6 F 5 , -C 8 F 7 , -Si(X 13 ) 3 , or -Ge(X 13 ) 3 , X 11 is an alkyl group or a halogen atom, X 12 is an alkyl group or -CF 3 , a plurality of X 13 are each independently an alkyl group, L Q is a single bond or a (1+n1)-valent group, n1 is an integer of 1 or more, and when there are a plurality of R Q , the plurality of R Q may be the same as or different from each other.

[0016] 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: That is, because the compound does not have a branched structure at the site that binds to the substrate, like the group P in this compound, 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, which is presumed to improve the oil repellency of the surface layer. In addition, 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 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.

[0017] The compound may contain only one P group, or two or more. In particular, from the viewpoint of superior adhesion to the substrate and abrasion resistance, the number of P groups in the compound is preferably 1 to 6, more preferably 1 to 4, even more preferably 1 to 2, and especially preferably 1.

[0018] 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.

[0019] Y 1 Each of these is independently a hydrolyzable group or a hydroxyl group. Among them, Y is preferred because it has superior adhesion to the substrate and abrasion resistance. 1 It is preferable that the group is hydrolyzable.

[0020] Y 1 In this context, the hydrolyzable group is a group that becomes a hydroxyl group through hydrolysis. That is, Si-Y 1A 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.

[0021] 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.

[0022] 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. 1 Because it exhibits less outgassing during application and provides superior storage stability for the compound, an alkoxy group having 1 to 4 carbon atoms is preferred, and an ethoxy group or a methoxy group is more preferred.

[0023] Y 2 Each of these is independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group. Among these, Y is preferred because it exhibits superior adhesion to the substrate and abrasion resistance. 2 It is preferable that the group is hydrolyzable.

[0024] Y 2 The hydrolyzable group in is the Y mentioned above. 1 This is synonymous with the hydrolyzable group in [the specified form], and the preferred embodiment is the same.

[0025] Y 2Examples of hydrocarbon groups in this compound include alkyl groups, cycloalkyl groups, alkenyl groups, and allyl groups, with alkyl groups being preferred from the viewpoint of ease of production. The number of carbon atoms in the hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.

[0026] Y 3 Each of these is independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and Y 3 At least one of these is a hydrolyzable group or a hydroxyl group. Among these, Y is preferred because it has superior storage stability. 3 It is preferable that the group is hydrolyzable.

[0027] Y 3 The hydrolyzable group in is the Y mentioned above. 1 This is synonymous with the hydrolyzable group in [the specified form], and the preferred embodiment is also the same. 3 The hydrocarbon group in is the Y mentioned above. 2 This is synonymous with a hydrocarbon group in [the specified form], and the preferred embodiment is the same.

[0028] In base P, there may be multiple Y 1 Y may have multiple properties. 2 , and multiple Y 3 Of these, at least two are hydrolyzable groups or hydroxyl groups. From the viewpoint of superior adhesion to the substrate and abrasion resistance, the total number of hydrolyzable groups and hydroxyl groups in base P is preferably 2 to 100, more preferably 5 to 20, and even more preferably 5 to 10. From the viewpoint of superior adhesion to the substrate and abrasion resistance, base 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.

[0029] L is - (CH 2 ) n - or an oxygen atom, where n is an integer of 1 or more and m is an integer of 2 or more, the multiple Ls may be the same or different from each other. n is preferably 1 to 20, more preferably 1 to 5, and even more preferably 1 to 3.

[0030] m is an integer greater than or equal to 1, and is preferably 1 to 30, more preferably 1 to 5, and even more preferably 1 to 3, from the standpoint of superior adhesion to the substrate and abrasion resistance.

[0031] A specific example of the base P is -Si(Cl) 2 -O-Si(Cl) 3 , -Si(OEt) 2 -O-Si(OEt) 3 , -Si(OMe) 2 -O-Si(OMe) 3 , -Si(OMe) 2 -O-Si(OMe) 2 -O-Si(OMe) 3 , -Si(OMe) 2 -O-Si(OMe) 2 -CH 2 -Si(OMe) 3 , -Si(OMe) 2 -O-Si(OMe) 2 -O-Si(OMe) 2 -O-Si(OMe) 3 -Si(Cl) 2 -CH 2 -Si(Cl) 3 , -Si(OMe) 2 -CH 2 -Si(OMe) 3 , -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(OMe) 2 - (CH 2 ) 2 -Si(OMe) 3 -Si(Cl)2 -(CH 2 ) 3 -Si(Cl) 3 、 -Si(OMe) 2 -(CH 2 ) 3 -Si(OMe) 3 、 -Si(Cl) 2 -(CH 2 ) 3 -Si(Cl) 3 、 -Si(OMe) 2 -(CH 2 ) 4 -Si(OMe) 3 、 -Si(OMe) 2 -(CH 2 ) 6 -Si(OMe) 3 、 -Si(OMe) 2 -(CH 2 ) 18 -Si(OMe) 3 、 -Si(OMe) 2 -CH 2 -Si(OMe) 2 -CH 2 -Si(OMe) 3 、 -Si(OMe) 2 -(CH 2 ) 2 -Si(OMe) 2 -(CH 2 ) 3 -Si(OMe) 3 、 -Si(OMe) 2 -(CH 2 ) 2 -Si(OMe) 2 -(CH 2 ) 2 -Si(OMe) 3 、 -Si(OMe) 2 -(CH 2 ) 2 -Si(OMe) 2 -CH 2 -Si(OMe) 3 、 -Si(OMe) 2 -(CH 2 ) 2 -Si(OMe) 2 -O-Si(OMe) 3, -Si(OMe) 2 -(CH 2 ) 3 -Si(OMe) 2 -CH 2 -Si(OMe) 3 , -Si(OMe) 2 -(CH 2 ) 3 -Si(OMe) 2 -O-Si(OMe) 3 , -Si(OMe) 2 -(CH 2 ) 10 -Si(OMe) 2 -CH 2 -Si(OMe) 3 , -Si(OMe) 2 -(CH 2 ) 14 -Si(OMe) 2 -CH 2 -Si(OMe) 3 , -Si(OMe) 2 -(CH 2 ) 18 -Si(OMe) 2 -CH 2 -Si(OMe) 3 , -Si(OMe) 2 -(CH 2 ) 3 -Si(OMe) 2 -CH 2 -Si(OMe) 2 -CH 2 -Si(OMe) 3 , -Si(OMe) 2 -CH 2 -Si(OMe) 2 -CH 2 -Si(OMe) 2 -CH 2 -Si(OMe) 2 -CH 2 -Si(OMe) 3 , and the like.

[0032] <Group Q> The compound may contain only one group Q, or two or more groups. In particular, from the viewpoint of superior oil-repellent effect, the number of groups Q in the compound is preferably 1 to 6, more preferably 1 to 4, even more preferably 1 to 2, and especially preferably 1.

[0033] When there are multiple groups Q in one molecule, the multiple groups Q may be identical or different from each other. From the viewpoint of the availability of raw materials and the ease of manufacturing the compound, it is preferable that the multiple groups Q are identical.

[0034] R Q is, -OCF 3 , -SCF 3 , -SF 4 X 11 , -N(CF 3 ) X 12 ,-CHF 2 ien-CH 2 F, -C 6 F 5 , -C 8 F 7 , -Si(X 13 ) 3 , or -Ge(X 13 ) 3 That is the case. Note that -C 6 F 5 This is a perfluorophenyl group, -C 8 F 7 It is a perfluorocubane ring group. Among them, -OCF is preferred because it has a superior oil-repellent effect. 3 , -SF 4 X 11 , -C 8 F 7、 -Si(X 13 ) 3 Preferably, -OCF 3 This is preferable. - SF 4 X 11 X in 11 X is an alkyl group or halogen atom. 11 The number of carbon atoms in the alkyl group is preferably 1 to 8, and more preferably 1 to 4. When the alkyl group has 3 or more carbon atoms, the alkyl group with 3 or more carbon atoms may be linear, branched, or have a cyclic structure. 11Specific examples of halogen atoms in this include F, Cl, Br, and I, with F being preferred because it provides superior oil repellency to the surface layer. -N(CF 3 ) X 12 X in 12 is an alkyl group or -CF 3 That is. X 12 The number of carbon atoms in the alkyl group is preferably 1 to 8, and more preferably 1 to 4. When the alkyl group has 3 or more carbon atoms, the alkyl group with 3 or more carbon atoms may be linear, branched, or have a ring structure. -Si(X 13 ) 3 and -Ge(X 13 ) 3 Multiple X in 13 Each of these is independently an alkyl group. 13 The number of carbon atoms in the alkyl group is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1. When the alkyl group has 3 or more carbon atoms, the alkyl group with 3 or more carbon atoms may be linear, branched, or have a cyclic structure. Q If there are multiple R Q They may be the same or different from one another.

[0035] L Q L is a single bond or a (1+n1) valence group. Q If the group is trivalent or higher, then L Q This is at least one branching point selected from the group consisting of N, C, Si, a cyclic hydrocarbon group which may contain an oxygen atom or a nitrogen atom as a ring member atom, and an organopolysiloxane residue (hereinafter referred to as "branching point P"). 1 It is written as ". ) has. N is branch point P 1 In the case where this occurs, branch point P 1 For example, *-N(-**) 2 It is represented as follows: However, * is J 1 The bond on the side (for example, if this compound is a compound represented by formula (1) described below, L 1 (The side joint) and ** is R Q This is a side joint. C is the branching point P. 1 In the case where this occurs, branch point P 1For example, *-C(-**) 3 or *-CR 11 (-**) 2 It is represented as follows: where * and ** are when N is the branching point P. 1 This is similar to the case where R 11 is a hydrogen atom or an alkyl group which may have -O-, and a hydrogen atom, a methyl group, or an ethyl group is preferred. Si is at branching point P 1 In the case where this occurs, branch point P 1 For example, *-Si(-**) 3 or *-SiR 11 (-**) 2 It is represented as follows: where * and ** are when N is the branching point P. 1 This is similar to the case where R 11 C is the branching point P. 1 This is similar to the case where this occurs.

[0036] The above R Q The side joint** is R Q It may bond directly to R, or it may bond via a linking group. That is, the bond ** is R Q -R 12 -* may be used in combination. However, R 12 R is a hydrocarbon group that may have a single bond or an -O- between carbon atoms, and * indicates the bond position. 12 The hydrocarbon groups in this context include aliphatic hydrocarbon groups (which may be saturated or unsaturated, and which may be linear, branched, or cyclic), aromatic hydrocarbon groups, and combinations thereof. Aliphatic hydrocarbon groups are preferred, and saturated aliphatic hydrocarbon groups are more preferred, due to their superior oil-repellent properties on the surface layer. 12 Among these, linear alkylene groups having 1 to 20 carbon atoms, which may have single bonds or -O- between carbon atoms, are preferred, more preferably 1 to 10 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 4 carbon atoms.

[0037] Branch point P 1A cyclic hydrocarbon group which may contain oxygen or nitrogen atoms as ring member atoms is a group which contains a ring structure which may contain oxygen or nitrogen atoms as ring member atoms. Specific examples of such ring structures include a 3- to 8-membered aliphatic ring, a 6-membered aromatic hydrocarbon ring, a 3- to 8-membered aliphatic heterocycle containing oxygen or nitrogen atoms as ring member atoms, a 5- to 6-membered aromatic heterocycle containing oxygen or nitrogen atoms as ring member atoms, and a fused ring consisting of two or more of these rings. More specifically, the following ring structures are shown. Note that in the following ring structures, J can be placed at any position of a hydrogen atom. 1 The side joints and n1 R Q -R 12 It has a bond with -*. In addition, any hydrogen atom may be substituted with a substituent. Examples of such substituents include halogen atoms such as fluorine atoms and chlorine atoms, and alkyl groups having 1 to 4 carbon atoms.

[0038]

[0039] L Q The (1+n1) valent organopolysiloxane residue in this compound may be linear or cyclic. The organopolysiloxane residue is preferably a group represented by the following formula (S1): *-(SiR 13 2 -O) nx -SiR 13 2 - (O) nx1 -** ... (S1) However, R 13 is a hydrogen atom, an alkyl group, and the R Q -R 12 - or J 1 The coupling on the side, nx is a number greater than or equal to 1, nx1 is 0 or 1, and if nx is 0, * and ** are the R 13 Therefore, when nx is 1, * and ** are linked together, and formula (S1) represents a cyclic polysiloxane residue.

[0040] The above R 13The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 2. nx is preferably 1 to 12, more preferably 1 to 6, and even more preferably 2 to 4.

[0041] If n1 is 1, L Q L is a single bond or a divalent group. Q Examples of divalent groups in this context include divalent cyclic hydrocarbon groups that may contain oxygen or nitrogen atoms as ring member atoms. The branching point P of the divalent cyclic hydrocarbon group. 1 Examples include the cyclic hydrocarbon group that constitutes it. A specific example of the divalent cyclic hydrocarbon group is the branching point P. 1 An example is the cyclic hydrocarbon group in which n1 is replaced with n1 in the description of a cyclic hydrocarbon group which may contain an oxygen atom or a nitrogen atom as a ring member atom.

[0042] L Q A preferred embodiment is a single bond, a hydrocarbon group which may have one or more -O- groups and one or more branching points P 1 A combination of the above, or branch point P 1 One example is an embodiment consisting solely of the above.

[0043] L Q A specific example of a group that does not contain a fluorine atom and has a valency of 3 or higher (1+n1) is *-C(-CH 2 -**) 3 , *-C (-C 3 H 6 -**) 3 , *-CH(-CH 2 -**) 2 , *-CH(-CH 2 -**) (-**), *-CH(-CH 2 -**)-CH(-**)-CH 2 (-**), *-CH(-**)-CH(-**)-CH(-**)-CH 2 (-**), *-CH(-**)-CH(-**)-CH(-**)-CH(-**)-CH 2 (-**), *-C(-CH 2 -**) 2 -CH 2 -O-CH(-CH 2-**) 2 , *-C(-CH 2 -**) 2 -CH 2 -O-CH 2 -C(-CH) 2 -**) 3 , *-SiCH 3 (-C 2 H 4 -**), *-N(-C 3 H 6 -**) 2 The following are examples of the base represented by the formula below. * is J 1 The bond on the side (for example, if this compound is a compound represented by formula (1) described below, L 1 (The side joint) and ** is R Q It is a side joint.

[0044]

[0045] In the above formula, qa is an integer from 1 to 5, the definitions of * and ** are as described above, and hydrogen atoms may be substituted with fluorine.

[0046] R Q n1, which represents the number, is an integer greater than or equal to 1. Here, if n1 is 1, L Q A single bond is preferred. On the other hand, if n2 is 2 or more, L Q The group is preferably a trivalent or higher (1+n1) valence group that does not contain a fluorine atom, and is more preferably a cyclic hydrocarbon group that may be substituted with a fluorine atom or may contain an oxygen atom or a nitrogen atom, or a trivalent or higher (1+n1) valence group that does not contain a fluorine atom (excluding cyclic hydrocarbon groups that may contain an oxygen atom or a nitrogen atom). The upper limit of n1 is preferably 10 and more preferably 4 from the viewpoint of ease of synthesis. Two or more R Q In cases where R Q These may have the same structure or they may have different structures.

[0047] <Preferred embodiment of the compound (Compound 1)> The compound represented by formula (1) (hereinafter referred to as "Compound 1") is preferred because it has superior oil repellency and abrasion resistance of the surface layer.

[0048] (R Q ) n1 -L Q -L 1 -L 2 - (J 1 ) n2 (1)

[0049] In formula (1), (R Q ) n1 -L Q - is a group represented by the above formula (Q), L 1 These are single bonds, or -O-, -C(=O)-, -C(=O)NX 14 -, -C(=O)O-, -NX 14 C(=O)-, -OC(=O)-, -NX 14 C(=O)NX 15 -, -NX 14 C(S)NX 15 -, -NX 14 C(=O)O-, -Si(X 14 ) 2 - A divalent hydrocarbon group which may have at least one group selected from the group consisting of a divalent organopolysiloxane residue and a divalent aromatic heterocycle, and if the divalent hydrocarbon group includes a cyclic hydrocarbon group, the cyclic hydrocarbon group may have substituents, X 14 and X 15 Each is independently a hydrogen atom or an alkyl group, L 2 is a single bond or a group with three or more (1+n2) valencies, J 1 is a base represented by the above formula (P), where n2 is an integer greater than or equal to 1, and when n2 is 1, L 2 It is a single bond, J 1 If there are multiple J 1 They may be identical or different from one another.

[0050] L 1Examples of divalent hydrocarbon groups include divalent saturated hydrocarbon groups, divalent unsaturated hydrocarbon groups, divalent aromatic hydrocarbon groups, and groups consisting of combinations thereof. Divalent saturated hydrocarbon groups may be linear, branched, or cyclic, and examples include alkylene groups and cycloalkylene groups. The number of carbon atoms in a divalent saturated hydrocarbon group is preferably 1 to 50, and more preferably 1 to 40. Cycloalkylene groups may have a monocyclic or polycyclic structure. Furthermore, cycloalkylene groups may have substituents described later. Divalent unsaturated hydrocarbon groups may be linear, branched, or cyclic, and examples include alkenylene groups, cycloalkenylene groups, and alkylylene groups. The number of carbon atoms in a divalent saturated hydrocarbon group is preferably 2 to 40. Cycloalkenylene groups may have a monocyclic or polycyclic structure. Furthermore, cycloalkenylene groups may have substituents described later. The divalent aromatic hydrocarbon group is preferably a group having 5 to 20 carbon atoms, for example, a phenylene group. The divalent aromatic hydrocarbon group may have a monocyclic or polycyclic structure and may have substituents as described later. 1 If the divalent hydrocarbon group in includes a cyclic hydrocarbon group (for example, the cycloalkylene group, the cycloalkenylene group, or the divalent aromatic hydrocarbon group mentioned above), the cyclic hydrocarbon group may have substituents. Specific examples of substituents include alkyl groups which may have -O- atoms, and halogen atoms.

[0051] L 1 The divalent hydrocarbon groups in are -O-, -C(=O)-, and -C(=O)NX 14 -, -C(=O)O-, -NX 14 C(=O)-, -OC(=O)-, -NX 14 C(=O)NX 15 -, -NX 14 C(=S)NX 15 -, -NX 14 C(=O)O-, -Si(X 14 ) 2 -, a divalent organopolysiloxane residue, and a divalent aromatic heterocycle (wherein X is used in the formula). 14 and X 15Each of these is independently a hydrogen atom or an alkyl group.) At least one group selected from the group consisting of (hereinafter referred to as "group W") 1 It may also be written as ". ) may have base W 1 -O-, -C(=O)O-, -Si(X) 14 ) 2 -, and -C(=O)NX 14 Preferably, it is at least one group selected from the group consisting of -O-, -C(=O)NX 14 - More preferably, the group is at least one selected from the group consisting of divalent organopolysiloxane residues. Group W 1 X in each group 14 and X 15 Each of these is independently either a hydrogen atom or an alkyl group. 14 and X 15 The number of carbon atoms in each alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. When the alkyl group has 3 or more carbon atoms, the alkyl group with 3 or more carbon atoms may be linear, branched, or have a ring structure. Group W 1 Specific examples of heteroatoms in the divalent aromatic heterocycle include O, S, and N. The divalent aromatic heterocycle is preferably a 5- to 10-membered ring, and more preferably a 5- to 6-membered ring. (W group) 1 In this, the divalent organopolysiloxane residue is -(SiR 14 2 -O) nx -SiR 14 2 - (where nx represents a number greater than or equal to 1, R 13 represents a hydrogen atom or an alkyl group. ) represents the group W 1 A specific example of a divalent organopolysiloxane residue in this is group B, which will be discussed later. 10 This is similar to a specific example of a divalent organopolysiloxane residue in [the relevant context].

[0052] L 1 L in 2 The base at the position where it bonds (hereinafter referred to as "base W") 2 It is also written as ". Specific examples include *-CH 2-**, *-C(=O)NX 14 -CH 2 -**, *-C(=O)NX 14 - (CH 2 ) 3 -**, *-C 6 H 4 -** can be mentioned. In the formula, X 14 As stated above, * is L 1 This indicates the binding site with the residue, and ** represents L 2 This indicates the connection point with [the other element].

[0053] L 1 L in Q The base at the position where it bonds (hereinafter referred to as "base W") 3 It is also written as ". Specific examples include *-CH 2 -**, *-C(=O)NX 14 -CH 2 -**, *-C(=O)NX 14 - (CH 2 ) 3 -**, *-C 6 H 4 -**, *-(SiR 14 2 -O) nx -SiR 14 2 -** can be mentioned. In the formula, X 14 and R 14 As stated above, * is L 1 This indicates the binding site with the residue, and ** represents L Q This indicates the connection point with [the other element].

[0054] L 1 The group is preferably represented by the following formula (L1): *-W 3 - (R 15 W 1 ) s1 -R 15 -W 2 -** ... (L1) However, W 1 , W 1 and W 3 As mentioned above, R 15 is a linear alkylene group, and s1 is an integer from 0 to 6.

[0055] Multiple R 15The total number of carbon atoms should be 1 or more, preferably 1 to 100, more preferably 6 to 50, and even more preferably 10 to 40. s1 is R 15 W 1 This represents the number of repetitions, and can be between 0 and 6, preferably between 0 and 3, and more preferably between 0 and 1.

[0056] In equation (1), L Q and L 1 It is preferable that the bond is not a single bond at the same time. That is, L Q If it is a single bond, L 1 is based on W 1 It is preferable that it is a divalent hydrocarbon group which may have L. 1 If it is a single bond, L Q It is preferable that the group is a trivalent or higher (1+n1) valent group that does not contain a fluorine atom.

[0057] L Q and L 1 If none of them are single bonds, (R Q ) n1 -L Q -L 1 In the group represented by -, L Q and L 1 The dividing line is L 1 The process is carried out in such a way that the number of carbon atoms in the divalent hydrocarbon group is maximized.

[0058] L 2 L is a single bond or a group with three or more (1+n2) valencies. 2 is, L Q It may be something similar to the above L. Q In the explanation, n1 is n2 and R Q J 1 And, J 1 is L 1 This should be interpreted as follows.

[0059] Here, if n2 is 1, L 2 This is a single bond. On the other hand, when n² is 2 or more, L 2 is a trivalent or higher (1+n2) valence group. The (1+n2) valence group is at least one branching point selected from the group consisting of C, N, Si, and a ring structure (hereinafter referred to as "branching point P").2 It is preferable to have the following:

[0060] Branch point P 2 The ring structure constituting the ring is preferably one selected from the group consisting of a 3- to 8-membered aliphatic ring, a 6-membered aromatic ring, a 5- to 6-membered heterocycle, and a fused ring consisting of two or more of these rings, from the viewpoint of ease of synthesis and superior friction resistance, light resistance, and chemical resistance of the surface layer, and the ring structure shown in the following formula is more preferred. The ring structure may have substituents such as halogen atoms, alkyl groups (which may contain etheric oxygen atoms between carbon atoms), cycloalkyl groups, alkenyl groups, alkoxy groups, and oxo groups (=O).

[0061]

[0062] L 2 If the base is a (1+n2) valence of 3 or more, L 2 This includes alkylene groups, hydroxyalkylene groups, alkoxyalkylene groups, carbonyl groups, amide bonds, ether bonds, thioether bonds, urea bonds, urethane bonds, carbonate bonds, ester bonds, and -SO 2 NR 26 -, -Si(R 26 ) 2 -, -OSi(R 26 ) 2 -, -NR 26 -, -Si(CH 3 ) 2 -Ph 1 -Si(CH 3 ) 2 - A group comprising one or more selected from divalent organopolysiloxane residues (hereinafter referred to as "group B") 10 It is written as ". ) may have. However, R 26 This is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph 1 This is a phenylene group. 26 The number of carbon atoms in the alkyl group is preferably 1 to 3, and more preferably 1 to 2, from the standpoint of facilitating the production of compound 1.

[0063] Examples of divalent organopolysiloxane residues include the group shown in the following formula. However, R in the following formula... 27 R is a hydrogen atom, an alkyl group, an alkoxy group, or a phenyl group. 27 The number of carbon atoms in the alkyl and alkoxy groups is preferably 1 to 10, and more preferably 1.

[0064]

[0065] L 2 If the base is a (1+n2) valence of 3 or more, L 2 From the standpoint of ease of synthesis, -C(=O)NR 26 -, -C(=O)-, -C(=O)O-, -NR 26 It is preferable to have at least one bond selected from the group consisting of - and -O-, and from the viewpoint of excellent light resistance and chemical resistance of the surface layer, -C(=O)NR 26 It is more preferable to have - or -C (=O)-.

[0066] L 2 If the base is a (1+n2) valence of 3 or more, L 2 A preferred form is one or more divalent hydrocarbon groups and one or more branching points P 2 A combination of, or one or more hydrocarbon groups and one or more branching points P 2 and one or more base B 10 A combination of these is one example. Specific examples of divalent hydrocarbon groups include divalent aliphatic hydrocarbon groups (alkylene groups, cycloalkylene groups, etc.) and divalent aromatic hydrocarbon groups (phenylene groups, etc.). The number of carbon atoms in the divalent hydrocarbon group is preferably 1 to 20. The number of carbon atoms in the divalent hydrocarbon group may be 1 to 6 or 1 to 4.

[0067] L 2 If the base is a (1+n2) valence of 3 or more, L 2 For example, *-C(-CH) 2 CH 2 CH 2 -**) 3 , *-CH(-CH 2 CH 2 CH 2 -**) 2, *-C(Me)(-CH 2 CH 2 CH 2 -**) 2 , *-Si(-CH 2 CH 2 CH 2 -**) 3 , *-SiH(-CH 2 CH 2 CH 2 -**) 2 , *-Si(Me)(-CH 2 CH 2 CH 2 -**) 2 , *-N(-CH 2 CH 2 CH 2 -**) 2 , *-CH(-CH 2 -O-CH 2 CH 2 CH 2 -**) 2 , *-Si(-CH 2 -**) (-**) 2 , *-CH(-C 11 H 22 -**) 2 , *-Si(-O-CH 2 CH 2 -**) (-CH 2 CH 2 CH 2 -**) 2 , *-C(-CH 2 -O-CH 2 CH 2 CH 2 -**) 3 The following groups are listed below. * indicates L 1 This indicates the connection position with, and ** represents J 1 This indicates the connection point with [the other element].

[0068]

[0069] L 1 and L 2 If none of them are single bonds, L 1 and L 2 The dividing line is L 1 The process is carried out in such a way that the number of carbon atoms in the divalent hydrocarbon group is maximized.

[0070] J 1 n², which represents the number of J, is an integer of 1 or more. From the viewpoint of ease of synthesis and ease of handling of compound 1, n² is preferably 1 to 6, more preferably 1 to 3, even more preferably 1 or 2, and particularly preferably 1. Two or more J 1 In cases where J 1 These may have the same structure or they may have different structures.

[0071] In equation (1), J 1 A group that directly bonds to J 1 The dividing line is J 1 {Si(Y 1 ) (Y 2 ) - L} m Perform the action in a way that maximizes the number.

[0072] (Preferred embodiment of the compound (compound 1-1)) The compound represented by formula (1-1) (hereinafter referred to as "compound 1-1") is preferred because it has superior oil repellency and abrasion resistance of the surface layer.

[0073]

[0074] In formula (1-1), L Q1 L is a single bond or a (1+n10) valent hydrocarbon group which may have -O- Q2 R is a cyclic hydrocarbon group which may contain N, C, Si, or an oxygen atom or a nitrogen atom as a ring member atom, 10 L is an alkyl group which may have a hydrogen atom or -O-. 21 L is a single bond or a group with three or more (1+n2) valencies. 22 is a hydrocarbon group which may have a single bond or an -O-, n10 is an integer of 1 or more, n11 is an integer of 1 or more, n12 is an integer of 0 or more, n13 is 0 or 1, L Q2 If is N, then n11 + n12 is 2, and L Q2 If is C or Si, then n11 + n12 is 3, and R Q , L 1 J 1, and n2 are R in equation (1), respectively. Q , L 1 J 1 , and is synonymous with n2, and if n13 is 0, then n10 and n11 are each 1, L Q1 It is a single bond, L 1 The above-mentioned base W 1 A divalent hydrocarbon group which may have (R Q ) n10 -L Q1 They may be the same or different from each other, and if n2 is 2 or more, there are multiple L 22 -J 1 These may be the same or different from each other, and if n12 is 2 or more, there are multiple R 10 They may be the same or different from one another.

[0075] L Q1 The (1+n10) valent hydrocarbon group in this compound includes aliphatic hydrocarbon groups (which may be saturated or unsaturated, and which may be linear, branched, or cyclic), aromatic hydrocarbon groups, and combinations thereof. From the viewpoint of ease of synthesis, aliphatic hydrocarbon groups are preferred, and saturated aliphatic hydrocarbon groups are more preferred. The number of carbon atoms in the (1+n10) valent hydrocarbon group is preferably 1 to 20. The number of carbon atoms in the (1+n10) valent hydrocarbon group may be 1 to 10, 1 to 6, or 1 to 4.

[0076] L Q2 This is a cyclic hydrocarbon group which may contain N, C, Si, or an oxygen or nitrogen atom as a ring member atom, and constitutes a branching point. 32 The definition is limited to cyclic hydrocarbon groups in which the ring structure may contain oxygen or nitrogen atoms as ring member atoms, except that the above L Q Branch point P explained above 1 It is synonymous with [the above].

[0077] R 10 R is an alkyl group which may have a hydrogen atom or -O-. 10The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. When the alkyl group has 3 or more carbon atoms, the alkyl group with 3 or more carbon atoms may be linear, branched, or have a ring structure.

[0078] n10 is an integer greater than or equal to 1, preferably between 1 and 5, and more preferably between 1 and 3. n11 is an integer greater than or equal to 1, preferably between 1 and 10, and more preferably between 1 and 4. n12 is an integer greater than or equal to 0, preferably between 0 and 4, and more preferably between 0 and 1. However, L Q2 If is N, then n11 + n12 is 2. Also, L Q2 If n11 is C or Si, then n11 + n12 is 3.

[0079] n13 is either 0 or 1. If n13 is 0, then n10 and n11 are each 1, and L Q1 This is a single bond. That is, when n13 is 0, equation (1-1) is one R Q is L 1 This structure directly bonds to the other element. Also, when n13 is 0, L 1 is the base W 1 It is a divalent hydrocarbon group which may have a . That is, when n13 is 0, L 1 It is not a single bond. 1 Details of the divalent hydrocarbon group which may have this property are as described above.

[0080] L 21 L is a single bond or a group with three or more (1+n2) valencies. 21 The (1+n2) valence group in may have heteroatoms such as N, O, S, and Si, and may have a branching point. 21 Medium L 1 and L 22 The atoms bonded are preferably, independently, N, O, S, Si, a carbon atom constituting a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O). 21 If it is a single bond, then L in equation (1-1) 1 and L 22 They bond directly. Also, L 21 It is a single bond, and L22 If it is a single bond, L 1 and J 1 They are directly bonded, and n2 is 1.

[0081] L 21 If the group is trivalent or higher, L 21 This is at least one branching point selected from the group consisting of C, N, Si, and a ring structure (hereinafter referred to as "branching point P"). 21 It is written as follows: )

[0082] N is the branching point P. 21 In the case where this occurs, branch point P 21 For example, *-N(-**) 2 It is represented as follows: where * is L 1 It is a side joint, and ** is L 22 This is a side joint. C is the branching point P. 21 In the case where this occurs, branch point P 21 For example, *-C(-**) 3 or *-CR 29 (-**) 2 It is represented as follows: where * and ** are when N is the branching point P. 21 This is similar to the case where R 29 This is a monovalent group, and examples include a hydrogen atom, a hydroxyl group, an alkyl group, and an alkoxy group. Si is at the branching point P. 21 In the case where this occurs, branch point P 21 For example, *-Si(-**) 3 or *-SiR 29 (-**) 2 It is represented as follows: where * and ** are when N is the branching point P. 21 This is similar to the case where R 29 C is the branching point P. 21 This is similar to the case where this occurs.

[0083] Branch point P 21 A specific example of the ring structure that constitutes it is the aforementioned branch point P. 2 This is similar to the ring structure in [the relevant context].

[0084] L with a valent or higher chromosome 21 is -C(=O)N(R 26 )-, -C(=O)O-, -C(=O)-, -C(OH)-, -O-, -N(R 26)-, -S-, -OC(=O)O-, -NHC(=O)O-, -NHC(=O)N(R 26 ) -, -SO 2 N(R) 26 )-,-N(R 26 ) SO 2 -, -Si(R 26 ) 2 -, -OSi(R 26 ) 2 -, and -Si(CH 3 ) 2 -Ph 1 -Si(CH 3 ) 2 - At least one type of bond selected from the group consisting of (hereinafter referred to as "bond B") 1 It is written as ". ) may have. However, R 26 This is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group, and Ph 1 This is a phenylene group. 26 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 compound 1-1.

[0085] Join B 1 From the standpoint of ease of synthesis, -C(=O)NR 26 -, -C(=O)-, and -NR 26 - At least one bond selected from the group consisting of - is preferred, and -C(=O)NR is preferred in terms of further superior light resistance and chemical resistance of the surface layer. 26 - or -C (=O)- is more preferable.

[0086] L with a valent or higher chromosome 21 is, L 1 and L 22 It is preferable that the atoms bonded to each are, independently, N, O, S, Si, a carbon atom constituting a branching point, or a carbon atom having a hydroxyl group or an oxo group (=O). That is, L 1 and L 22 Each adjacent atom is bonded to B 1 Or branching point P 21 It is preferable that it is a constituent element of L with a valency of 3 or higher. 21 A concrete example of this is one or more branching points P. 21 (For example {*-P21 (-**) n2}), one or more branching points P 21 and one or more bonds B 1 A combination with (for example, {*-B 1 -R 28 -P 21 (-**) n2}, {*-B 1 -R 28 -P 21 (-R 28 -B 1 -**) n2}) can be cited. However, R 28 * is a single bond or a divalent organic group, and * is L 1 It is a side joint, and ** is L 22 It is a side joint.

[0087] The above R 28 Examples of divalent organic groups in this context include divalent aliphatic hydrocarbon groups (alkylene groups, cycloalkylene groups, etc.) and divalent aromatic hydrocarbon groups (phenylene groups, etc.), where a bond exists between carbon atoms of a hydrocarbon group having two or more carbon atoms. 1 It may have a divalent organic group. The number of carbon atoms in the divalent organic group is preferably 1 to 20. The number of carbon atoms in the divalent organic group may be 1 to 6 or 1 to 4.

[0088] L with a valent or higher chromosome 21 As such, a group represented by any of the following formulas (E1) to (E5) and (E7) is preferred because it facilitates the production of compound 1-1.

[0089] -E 1 -C(R E2 ) 3-e3 (-E 22 -) e3 (E2) -E 2 -N(-E 23 -) 2 (E3) -E 3 -Z 1 (-E 24 -) e4 (E4) -E 2 -Si(R E3 ) 3-e3 (-E 25 -)e3 (E5) -E 1 -CH(-E 22 -)-Si(R E3 ) 3-e5 (-E 25 -) e5 (E7) However, in formulas (E1) to (E5) and (E7), E 1 , E 2 or E 3 The side is L in equation (1-1) 1 Connect to E 22 , E 23 , E 24 or E 25 The side is L 22 Connect to E. 1 is a single bond, or -B 5 - and B 5 is -C(=O)NR E6 -, -C(=O)-, -NR E6 - or -O-, E 2 is a single bond or -C(=O)-, E 3 is, E 3 Z that joins 1 If the atom in is a carbon atom, then E 1 E 3 Z that joins 1 If the atom in is a nitrogen atom, E 2 E 11 This refers to a single bond, -O-, an alkylene group, or an alkylene group with two or more carbon atoms with -C(=O)NR between carbon atoms. E6 -, -C(=O)-, -NR E6 A group having - or -O-, E 22 is a single bond, -B 5 -, -R 40 -B 6 - or -B 5 -R 40 -B 6 - and E 22 If you have two or more E 22 They may be the same or different, R 40 This is an alkylene group, or an alkylene group having 2 or more carbon atoms with -C(=O)NR between carbon atoms. E6-, -C(=O)-, -NR E6 A group having - or -O-, B 6 Ha - C(=O)NR E6 -, -C (=O)-, or -NR E6 - and E 23 is a single bond or -R 40 -B 6 - and two E 23 They may be the same or different, E 24 is, E 24 Z that joins 1 If the atom in is a carbon atom, then E 22 E 24 Z that joins 1 If the atom in is a nitrogen atom, E 23 E 24 If you have two or more E 24 They may be the same or different, E 25 This is a single bond, or -R 40 -B 6 - and E 25 If you have two or more E 25 They may be the same or different, Z 1 is, E 3 It has a carbon or nitrogen atom that is directly bonded to it and E 24 R is a group having a (e4+1) 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, R E2 R is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group. E3 R is an alkyl group. E6 e1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. e1 is an integer from 0 to 2, e2 is an integer from 0 to 3, e1 + e2 is an integer from 1 to 5, e3 is an integer from 1 to 3, e4 is an integer greater than or equal to 1, and e5 is an integer from 1 to 3. Note that e1 + e2 = n2, e3 = n2, e4 = n2, and e5 + 1 = n2.

[0090] R 40 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, from the standpoint of facilitating the production of compound 1-1 and further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. 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.

[0091] Z 1 The ring structure in is the ring structure described above, and the preferred form is also the same. 1 The ring structure in E 24 Because they bond directly, for example, an alkylene group is linked to the ring structure, and E is attached to that alkylene group. 24 They will not be connected.

[0092] 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 even more preferably 1 to 2, from the standpoint of facilitating the production of compound 1-1. 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 even more preferably 1 to 2, from the standpoint of facilitating the production of compound 1-1. For e4, the number of carbon atoms is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3, from the standpoint of facilitating the production of compound 1-1 and further improving the abrasion resistance and fingerprint removal properties of the surface layer.

[0093] L 11 Other forms include groups represented by any of the following formulas (E11) to (E15) and (E17).

[0094] -E 1 -C(R E2 ) 3-e3 (-E 22 -E G ) e3 (E12) -E 2 -N(-E 23 -E G ) 2 (E13) -E 3 -Z 1 (-E 24 -EG ) e4 (E14) -E 2 -Si(R E3 ) 3-e3 (-E 25 -E G ) e3 (E15) -E 1 -CH(-E 22 -)-Si(R E3 ) 3-e5 (-E 25 -E G ) e5 (E17)

[0095] Provided that in formulas (E11) to (E15) and (E17), the E 1 , E 2 or E 3 side connects to L of formula (1-1), 1 and the E 22 , E 23 , E 24 or E 25 side connects to L 22 . E G is represented by the following formula (E G ), two or more E 21 contained in L G may be the same or different. Reference signs other than E G are the same as the reference signs in formulas (E1) to (E5) and (E7). -Si(R 23 ) 3-k (-E 30 -) k (E G ) Provided that in formula (E G ), the Si side connects to E 22 , E 23 , E 24 or E 25 , and the E 30 side connects to L 22 . R 23 is an alkyl group. E 30 is a single bond or -R 45 -B 6 -, wherein R 45 is an alkylene group, or -C(=O)NR 46 -, -C(=O)-, -NR46 A group having - or -O-, or -(OSi(R 24 ) 2 ) p -O- and 2 or more E 30 They may be the same or different. k is 2 or 3. R 46 R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. 24 is an alkyl group, a phenyl group, or an alkoxy group, and has two R 24 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 24 ) 2 ) may be the same or different.

[0096] E 30 The number of carbon atoms in the alkylene group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, from the standpoint of facilitating the production of compound 1-1 and further improving the abrasion resistance, light resistance, and chemical resistance of the surface layer. 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. 23 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 compound 1-1. 24 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 compound 1-1. 24 The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2, from the viewpoint of excellent storage stability of compound 1-1. p is preferably 0 or 1.

[0097] L 22 This is a hydrocarbon group that may have a single bond or an -O-. Examples of hydrocarbon groups include aliphatic hydrocarbon groups (which may be saturated or unsaturated, and may be linear, branched, or cyclic), aromatic hydrocarbon groups, and combinations thereof. From the standpoint of excellent durability as a surface layer, aliphatic hydrocarbon groups are preferred, saturated aliphatic hydrocarbon groups are more preferred, and alkylene groups are even more preferred. 22When there are a plurality of L 22 , they may be the same as or different from each other. L 22 The number of carbon atoms in the hydrocarbon group in is preferably 1 to 20, more preferably 1 to 15, and still more preferably 1 to 11. When the hydrocarbon group has 3 or more carbon atoms, the hydrocarbon group having 3 or more carbon atoms may be linear, or may have a branched or cyclic structure. In a hydrocarbon group containing -O-, the atom bonded to L 21 may be -O-, or -O- may be present between carbon atoms.

[0098] L 22 is preferably a group represented by the following formula (H1): *-(O) a4 -(L g11 O) a5 -L g12 -** (H1) wherein L g11 is an alkylene group having 1 to 12 carbon atoms, and when there are a plurality of L g11 , when there are a plurality of L g11 , the plurality of L g12 may be the same as or different from each other, L is an alkylene group having 1 to 12 carbon atoms, a4 is 0 or 1, a5 is an integer of 0 or more, * is a binding bond bonded to L 21 , and ** is a binding bond bonded to J 1 .

[0099] When a4 is 0, the atom having the binding bond * is a carbon atom, and when a4 is 1, the atom having the binding bond * is an oxygen atom. In compound 1-1, a4 may be either 0 or 1, and may be appropriately selected from the viewpoint of ease of synthesis and the like. a5 is the number of repetitions of L g11 O, and from the viewpoint of excellent durability as a surface layer, a5 is preferably 0 to 6, more preferably 0 to 3, and still more preferably 0 to 1. The alkylene group of L g11 may be a linear or branched alkylene group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 1 to 3 carbon atoms. Further, the alkylene group is preferably a linear alkylene group. L g12The alkylene group may be any linear or branched alkylene group having 1 to 12 carbon atoms, and a linear alkylene group is preferred.

[0100] A specific example of this compound is the compound represented by the following formula.

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] <Physical Properties of the Compound> The molecular weight of this compound is preferably 200 to 10,000, and more preferably 300 to 5,000. If the molecular weight of this compound is above the lower limit of the above range, the wear resistance of the surface layer is better. If the molecular weight of this compound is below the upper limit of the above range, the viscosity is easier to adjust to an appropriate range, and the solubility is improved, resulting in excellent handling during film formation.

[0111] [Surface Treatment Agent] The surface treatment agent of this embodiment (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 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.

[0112] 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.

[0113] 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), C2 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), C 4 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.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] Specific examples of ether-based organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.

[0118] 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.

[0119] 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.

[0120] Other organic solvents include chlorinated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds.

[0121] 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.

[0122] Specific examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.

[0123] Specific examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0124] Specific examples of siloxane compounds include hexamethyldisiloxane, octamethyltrisiloxane, and decamethyltetrasiloxane.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] [Article] The article of this embodiment (hereinafter referred to as "this article") has a surface layer formed from the compound or the surface treatment agent on the surface of a substrate. An example of this 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 this 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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:

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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.

[0140] Another example of the present article 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 present compound.

[0141] 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.

[0142] Specific examples of this article include optical components, touch panels, anti-reflective films, anti-reflective glass, and SiO 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.

[0143] [Method for Manufacturing Articles] The method for manufacturing these articles is to form a surface layer using the compound or the surface treatment agent by a dry coating method or a wet coating method.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] The present invention will be described in detail below with reference to examples. Of Examples 1 to 13, Examples 1 to 12 are examples, and Example 13 is a comparative example. However, the present invention is not limited to these examples.

[0148] [Example 1] <Synthesis of Compound X> Under a nitrogen atmosphere, 1,1,1,3,3-pentachloro-1,3-disilapropane (5.0 g), synthesized by the method described in Chem. Eur. J. 2014, 20, 9442, was mixed with 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.

[0149]

[0150] <Synthesis of Compound 1A> To 18-(trifluoromethoxy)-1-octadecene (500 mg) dissolved in dichloromethane (5 mL), a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 19 mg), aniline (1.4 mg), and compound X (60% by mass, 1.1 g) were added, and the mixture was stirred at 25°C for 15 hours. The solvent was removed by distillation under reduced pressure, and the resulting crude solution was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 600 mg of compound 1A. The structure of compound 1A was confirmed from the following NMR data.

[0151]

[0152] (NMR spectrum of compound 1A) 1 H-NMR (400MHz, CDCl3) δ 3.96 (t ,2H), 3.57 (s, 9H), 3.53 (s, 6H), 1.70 - 1.64 (m, 2H), 1.42 - 1.17 (m, 30H), 0.70 - 0.66 (m, 2H), - 0.03 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.9.

[0153] [Example 2] <Synthesis of Compound A> 10 g of 18-bromo-1-octadecene was mixed with 10 g of THF (tetrahydrofuran), a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 5 mg), and 10 g of chlorodimethylsilane, and the mixture was stirred at 25°C for 24 hours. By removing the low-boiling components under reduced pressure, 12 g of Compound A was obtained.

[0154]

[0155] (NMR spectrum of compound A) 1 H-NMR (400 MHz, CDCl3) δ 3.40 (t, J = 6.9 Hz, 2H), 1.92 - 1.74 (m, 2H), 1.46 - 1.06 (m, 30H), 0.88 - 0.71 (m, 2H), 0.40 (s, 6H).

[0156] <Synthesis of Compound B> Compound A (12 g) was mixed with THF (10 g) and a THF solution of methylmagnesium chloride (1.0 mol / L) (40 mL) and stirred at 25°C for 1 hour. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were removed by distillation under reduced pressure. Then, 8 g of compound B was obtained by flash column chromatography using silica gel (developing solvent: hexane / dichloromethane).

[0157]

[0158] (NMR spectrum of compound B) 1 H-NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.85 (p, J = 7.0 Hz, 2H), 1.46 - 1.06 (m, 30H), 0.47 (t, J = 7.6 Hz, 2H), -0.03(s, 9H).

[0159] <Synthesis of Compound C> 10 g of 11-bromo-1-undecene was mixed with 20 g of THF and 1.1 g of magnesium, and the mixture was stirred at 60°C for 2 hours. The reaction mixture was filtered to obtain 30 g of Compound C. The concentration of the product was confirmed to be 0.8 mol / L by titration using 1,10-phenanthroline.

[0160]

[0161] <Synthesis of Compound D> Compound B (1.0 g) was mixed with THF (10 g), Compound C (0.8 mol / L) (10 mL), and copper(II) chloride (0.05 g), and the mixture was stirred at 60°C for 24 hours. Hydrochloric acid and hexane were added for extraction, and low-boiling point components were removed by distillation under reduced pressure. Then, 0.40 g of Compound D was obtained by flash column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane). The structure of Compound D was confirmed from the following NMR data.

[0162]

[0163] (NMR spectrum of compound D) 1 H-NMR (400 MHz, CDCl3) δ 5.82 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.09 - 4.78 (m, 2H), 2.04 (q, J = 7.1 Hz, 2H), 1.46 - 1.06 (m, 50H), 0.47 (t, J = 7.7 Hz, 2H), -0.03(s, 9H).

[0164] <Synthesis of Compound 1B> Compound 1B was obtained in 510 mg using the same procedure as the synthesis of Compound 1A, except that Compound D (400 mg) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1B was confirmed from the following NMR data.

[0165]

[0166] (NMR spectrum of compound 1B) 1H-NMR (400 MHz, CDCl3) δ3.57 (s, 9H), 3.53 (s, 6H), 1.46 - 1.06 (m, 54H), 0.70 - 0.65 (m, 2H), 0.47 (t, J = 7.7 Hz, 2H), - 0.03 (m, 11H).

[0167] [Example 3] <Synthesis of Compound 1C> Compound 1C was obtained in 700 mg using the same procedure as in the synthesis of Compound 1A, except that 1,1,1,3,3-pentamethoxydisiloxane (95% by mass, 710 mg) was used instead of Compound X (60% by mass). The structure of Compound 1C was confirmed from the following NMR data.

[0168]

[0169] (NMR spectrum of compound 1C) 1 H-NMR (400MHz, CDCl3) δ 3.94 (t ,2H), 3.59 (s, 9H), 3.57 (s, 6H), 1.69 - 1.64 (m, 2H), 1.39 - 1.20 (m, 30H), 0.70 - 0.61 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.9.

[0170] [Example 4] <Synthesis of Compound E> Under a nitrogen atmosphere, dimethyl malonate (3.0 g), dried dimethylformamide (50 mL), dried THF (50 mL), and 60% sodium hydride (dispersed in liquid paraffin, 0.75 g) were added and stirred at 25°C for 10 minutes. Then, 18-bromo-1-octadecene (5.0 g) was added and heated to 60°C and stirred for 5 hours. Next, water was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine, dried over magnesium sulfate, and then the solvent and low-boiling components were removed by reduced pressure distillation. The low-boiling components were removed by reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 5.8 g of compound E. The structure of compound E was confirmed from the following NMR data.

[0171]

[0172] (NMR spectrum of compound E) 1 H-NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.2, 10.3, 6.7, 2H),5.02 - 4.91 (m, 1H), 3.74 (s, 6H), 3.36 (t, J = 7.6 Hz, 1H), 2.06 - 2.01 (m, 2H),1.92 - 1.86 (m, 2H), 1.39 - 1.25 (m, 28H).

[0173] <Synthesis of Compound F> Under a nitrogen atmosphere, lithium aluminum hydride (0.62 g) and dry THF (10 mL) were mixed, and the resulting suspension was cooled to 0°C. Next, compound E (2.5 g) dissolved in dry THF (15 mL) was added dropwise, and the mixture was stirred at 0°C for 15 minutes. Then, the temperature was raised to 25°C and the mixture was stirred for a further 2 hours. Next, the reaction mixture was cooled again to 0°C, and the reaction was terminated by adding saturated sodium sulfate aqueous solution dropwise. The resulting precipitate was filtered off using Celite, the residue was washed with THF, and the low-boiling point components of the obtained filtrate were removed under reduced pressure. The obtained solid was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 1.5 g of compound F. The structure of compound F was confirmed from the following NMR data.

[0174]

[0175] (NMR spectrum of compound F) 1 H-NMR (400MHz, CDCl3) δ5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.02 - 4.91 (m, 1H), 3.85 - 3.80 (m, 2H), 3.69 - 3.63 (m, 2H), 2.11 (t, J = 5.5 Hz, 2H), 2.06 - 2.01 (m, 2H), 1.81 - 1.74 (m, 1H), 1.39 - 1.21 (m, 30H).

[0176] <Synthesis of Compound G> Under a nitrogen atmosphere, compound F (1.5 g), silver trifluoromethanesulfonate (12 g), cesium fluoride (8.4 g), Selectfluor® (registered trademark, manufactured by Tokyo Chemical Industry Co., Ltd., 6.5 g), 2-pyridine fluoride (4.0 mL), and dry toluene (40 mL) were added to a flask in a glove box and stirred at 25°C for 10 minutes. Then, (trifluoromethyl)trimethylsilane (6.8 mL) was added dropwise over 5 minutes while stirring, and the mixture was stirred at 25°C for a further 15 hours. The precipitate formed after the reaction was filtered off using Celite, the residue was washed with hexane, and the low-boiling components of the obtained filtrate were removed under reduced pressure. The obtained crude solution was purified by silica gel column chromatography (eluent: hexane) to obtain 1.2 g of compound G. The structure of compound G was confirmed from the following NMR data.

[0177]

[0178] (NMR spectrum of compound G) 1 H-NMR (400MHz, CDCl3) δ5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.02 - 4.91 (m, 1H), 3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 2.06 - 2.01 (m, 3H), 1.41 - 1.26 (m, 30H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0179] <Synthesis of Compound 1D> Compound 1D was obtained in 320 mg using the same procedure as the synthesis of Compound 1A, except that Compound G (500 mg) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1D was confirmed from the following NMR data.

[0180]

[0181] (NMR spectrum of compound 1D) 1H-NMR (400MHz, CDCl3) δ4.00 (dd, J = 9.8 Hz, 4.9 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.4 Hz, 2H), 3.57 (s, 9H), 3.52 (s, 6H), 2.05 - 2.00 (m, 1H), 1.40 - 1.25 (m, 34H), 0.70 - 0.67 (m, 2H), - 0.03 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0182] [Example 5] <Synthesis of Compound H> Compound G (500 mg) dissolved in dichloromethane (1 mL) was mixed with a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 14 mg), aniline (1.0 mg), and trimethoxysilane (200 mg), and stirred at 25°C for 2 hours. By removing the solvent under reduced pressure, 630 mg of compound H was obtained. The structure of compound H was confirmed from the following NMR data.

[0183]

[0184] (NMR spectrum of compound H) 1 H-NMR (400MHz, CDCl3) δ3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.57 (s, 9H), 2.06 - 2.01 (m, 1H), 1.39 - 1.26 (m, 34H), 0.67 - 0.63 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0185] <Synthesis of Compound J> Compound H (630 mg) was mixed with THF (3.0 g) and a THF solution of allyl magnesium chloride (2.0 M) (0.54 mL), and the mixture was stirred at 0°C for 1 hour. Then, it was stirred at 25°C for 17 hours. After removing the low-boiling point components under reduced pressure, 450 mg of compound J was obtained by flash column chromatography using silica gel (developing solvent: hexane / ethyl acetate). The structure of compound J was confirmed from the following NMR data.

[0186]

[0187] (NMR spectrum of compound J) 1 H-NMR (400MHz, CDCl3) δ5.87 - 5.76 (m, 1H), 4.96 - 4.88 (m, 2H), 3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.54 (s, 6H), 2.06 - 2.01 (m, 1H), 1.70 - 1.61 (m, 2H), 1.39 - 1.26 (m, 34H), 0.70 - 0.62 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.1.

[0188] <Synthesis of Compound 1E> Compound 1E was obtained in 260 mg using the same procedure as the synthesis of Compound 1A, except that Compound J (450 mg) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1E was confirmed from the following NMR data.

[0189]

[0190] (NMR spectrum of compound 1E) 1H-NMR (400MHz, CDCl3) δ3.99 (dd, J = 9.8 Hz, 4.5 Hz, 2H), 3.95 (dd, J = 9.8 Hz, 6.2 Hz, 2H), 3.57 (s, 9H), 3.53 (s, 12H), 2.06 - 2.00 (m, 1H), 1.42 - 1.26 (m, 36H), 0.76 - 0.69 (m, 4H), 0.66 - 0.61 (m, 2H), -0.03 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.3.

[0191] [Example 6] <Synthesis of Compound K> Under a nitrogen atmosphere, 2.5 g of 2-phenyl-1,3-dioxan-5-ol was added to 50 mL of dried dimethylformamide and 1.4 g of 60% sodium hydride (dispersed in liquid paraffin), and the mixture was stirred at 25°C for 10 minutes. Then, 9.2 g of 18-bromo-1-octadecene was added, and the mixture was stirred at 25°C for a further 2 hours. Next, water was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine, dried over magnesium sulfate, and then the solvent and low-boiling components were removed by vacuum distillation. After removing the low-boiling components by vacuum distillation, the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 6.0 g of compound K. The structure of compound K was confirmed from the following NMR data.

[0192]

[0193] (NMR spectrum of compound K) 1H-NMR (400MHz, CDCl3) δ7.52 - 7.50 (m, 2H), 7.37 - 7.32 (m, 3H), 5.82 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.55 (s, 1H), 5.02 - 4.91 (m, 1H), 4.34 (dd, J = 12.4 Hz, 1.2 Hz, 2H), 4.05 (dd, J = 12.4 Hz, 1.4 Hz, 2H), 3.55 (t, J = 6.9 Hz, 2H), 3.27 - 3.25 (m, 1H), 2.06 - 2.01 (m, 2H), 1.68 - 1.61 (m, 2H), 1.39 - 1.24 (m, 26H).

[0194] <Synthesis of Compound L> Compound K (6.0 g) was dispersed in methanol (100 mL), p-toluenesulfonic acid monohydrate (1.5 g) was added, and the mixture was stirred at 25°C for 6 hours. Next, saturated sodium bicarbonate solution was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine, dried over magnesium sulfate, and then the solvent and low-boiling components were removed by reduced pressure distillation. The low-boiling components were removed by reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 4.2 g of compound L. The structure of compound L was confirmed from the following NMR data.

[0195]

[0196] (NMR spectrum of compound L) 1 H-NMR (400MHz, CDCl3) δ5.81 (ddt, J = 16.9 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.02 - 4.91 (m, 1H), 3.80 - 3.65 (m, 4H), 3.57 (t, J = 6.7 Hz, 2H), 3.46 (quint, J = 5.0 Hz, 1H), 2.07 - 2.01 (m, 2H), 1.93 (d, J = 6.0 Hz, 2H), 1.63 - 1.56 (m, 2H), 1.39 - 1.25 (m, 26H).

[0197] <Synthesis of Compound M> Compound M was obtained in 700 mg using the same procedure as the synthesis of Compound G, except that Compound L (2.3 g) was used instead of Compound F. The structure of Compound M was confirmed from the following NMR data.

[0198]

[0199] (NMR spectrum of compound M) 1 H-NMR (400MHz, CDCl3) δ5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.02 - 4.91 (m, 1H), 4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.0 Hz, 1H), 3.57 (t, J = 6.4 Hz, 2H), 2.06 - 2.01 (m, 2H), 1.61 - 1.52 (m, 2H), 1.39 - 1.22 (m, 26H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0200] <Synthesis of Compound 1F> Compound 1F was obtained in 350 mg using the same procedure as the synthesis of Compound 1A, except that Compound M (500 mg) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1F was confirmed from the following NMR data.

[0201]

[0202] (NMR spectrum of compound 1F) 1 H-NMR (400MHz, CDCl3) δ4.07 - 3.99 (m, 4H), 3.73 (quint, J = 5.0 Hz, 1H), 3.58- 3.56 (m, 11H), 3.52 (s, 6H), 1.61 - 1.53 (m, 2H), 1.40 - 1.25 (m, 30H), 0.70 - 0.66 (m, 2H), - 0.03 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.2.

[0203] [Example 7] <Synthesis of Compound N> Compound N was obtained in 620 mg using the same procedure as in the synthesis of Compound H, except that Compound M (500 mg) was used instead of Compound G. The structure of Compound N was confirmed from the following NMR data.

[0204]

[0205] (NMR spectrum of compound N) 1 H-NMR (400 MHz, CDCl3) δ4.07 - 3.99 (m, 4H), 3.74 (quint, J = 5.3 Hz, 1H), 3.59 - 3.56 (m, 11H), 1.61 - 1.54 (m, 2H), 1.41 - 1.25 (m, 30H), 0.67 - 0.63 (m, 2H). 19 F-NMR (376 MHz, CDCl3) δ-61.2.

[0206] <Synthesis of Compound P> Compound P was obtained using the same procedure as the synthesis of Compound J, except that Compound N (620 mg) was used instead of Compound H. The structure of Compound P was confirmed from the following NMR data.

[0207]

[0208] (NMR spectrum of compound P) 1 H-NMR (400 MHz, CDCl3) δ5.87 - 5.76 (m, 1H), 4.96 - 4.88 (m, 2H), 4.07 - 3.99 (m, 4H), 3.74 (quint, J = 5.3 Hz, 1H), 3.59 - 3.54 (m, 8H), 1.70 - 1.54 (m, 4H), 1.41 - 1.24 (m, 30H), 0.70 - 0.60 (m, 2H). 19 F-NMR (376 MHz, CDCl3) δ-61.4.

[0209] <Synthesis of Compound 1G> Compound 1G was obtained in 250 mg using the same procedure as the synthesis of Compound 1A, except that Compound P (420 mg) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1G was confirmed from the following NMR data.

[0210]

[0211] (NMR spectrum of compound 1G) 1 H-NMR (400 MHz, CDCl3) δ4.07 - 4.00 (m, 4H), 3.74 (quint, J = 5.3 Hz, 1H), 3.59 - 3.53 (m, 17H), 1.61 - 1.53 (m, 2H), 1.41 - 1.24 (m, 32H), 0.76 - 0.69 (m, 4H), 0.66 - 0.62 (m, 2H). 19 F-NMR (376 MHz, CDCl3) δ-61.2.

[0212] [Example 8] <Synthesis of Compound Q> Under a nitrogen atmosphere, pentaerythritol monobenzyl ether (1.0 g), silver trifluoromethanesulfonate (17 g), cesium fluoride (12 g), Selectfluor® (registered trademark, manufactured by Tokyo Chemical Industry Co., Ltd., 19 g), 2-pyridine fluoride (5.7 mL), and dry toluene (100 mL) were added to a flask in a glove box and stirred at 25°C for 10 minutes. Then, (trifluoromethyl)trimethylsilane (9.8 mL) was added dropwise over 5 minutes while stirring, and the mixture was stirred for a further 15 hours at 25°C. The precipitate formed after the reaction was filtered off using Celite, the residue was washed with hexane, and the low-boiling point components of the obtained filtrate were removed under reduced pressure. The obtained crude solution was purified by silica gel column chromatography (developing solvent: hexane) to obtain 1.0 g of compound Q. The structure of compound Q was confirmed from the following NMR data.

[0213]

[0214] (NMR spectrum of compound Q) 1H-NMR (400MHz, CDCl3) δ 7.39 - 7.28 (m, 5H), 4.52 (s, 2H), 4.04 (s, 6H), 3.49 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-62.9.

[0215] <Synthesis of Compound R> Compound Q (1.0 g) and methanol (15 mL) were added to a round-bottom flask and stirred at 25°C until homogeneous. Next, 10% palladium-carbon (1.0 g) was added and the gas in the flask was replaced with a hydrogen atmosphere. The reaction suspension was stirred at 25°C for 15 hours, and the precipitate was removed by passing it through Celite. The low-boiling point components of the obtained filtrate were removed under reduced pressure, and the resulting crude solution was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 760 mg of compound R. The structure of compound R was confirmed from the following NMR data.

[0216]

[0217] (NMR spectrum of compound R) 1 H-NMR (400MHz, CDCl3) δ4.05 (s, 6H), 3.74 (d, J = 5.0 Hz, 2H), 1.63 (t, J = 5.0 Hz, 1H). 19 F-NMR (376MHz, CDCl3) δ-62.9.

[0218] <Synthesis of Compound S> Under a nitrogen atmosphere, 270 mg of compound R was added to 10 mL of dried dimethylformamide and 110 mg of 60% sodium hydride (dispersed in liquid paraffin), and the mixture was stirred at 25°C for 10 minutes. Then, 980 mg of 18-iodo-1-octadecene was added, and the mixture was stirred at 25°C for a further 15 hours. Next, water was added to the mixture to terminate the reaction, and ethyl acetate was added to separate the organic phase. The organic phase was washed with water and saturated brine, dried over magnesium sulfate, and then the solvent and low-boiling components were removed by reduced pressure distillation. After removing the low-boiling components by reduced pressure, the resulting crude solution was purified by silica gel column chromatography (developing solvent: hexane) to obtain 190 mg of compound S. The structure of compound S was confirmed from the following NMR data.

[0219]

[0220] (NMR spectrum of compound S) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 2H), 5.02 - 4.91 (m, 1H), 4.02 (s, 6H), 3.43 - 3.40 (m, 4H), 2.07 - 2.01 (m, 2H), 1.56 - 1.51 (m, 2H), 1.39 - 1.26 (m, 26H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0221] <Synthesis of Compound 1H> Compound 1H was obtained in 460 mg using the same procedure as the synthesis of Compound 1A, except that Compound S (500 mg) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1H was confirmed from the following NMR data.

[0222]

[0223] (NMR spectrum of compound 1H) 1 H-NMR (400MHz, CDCl3) δ 4.02 (s, 6H), 3.57 (s, 9H), 3.53 (s, 6H), 3.42 - 3.40 (m, 4H), 1.56 - 1.51 (m, 2H), 1.35 - 1.26 (m, 28H), 0.70 - 0.66 (m, 2H), - 0.03 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0224] [Example 9] <Synthesis of Compound 1J> Compound 1J was obtained in 580 mg using the same procedure as in the synthesis of Compound 1A, except that Compound S (500 mg) was used instead of 18-bromo-1-octadecene and 1,1,1,3,3-pentamethoxydisiloxane (95% by mass, 300 mg) was used instead of Compound X (60% by mass). The structure of Compound 1J was confirmed from the following NMR data.

[0225]

[0226] (NMR spectrum of compound 1J) 1 H-NMR (400MHz, CDCl3) δ 4.02 (s, 6H), 3.59 (s, 9H), 3.57 (s, 6H), 3.42 - 3.40 (m, 4H), 1.56 - 1.51 (m, 2H), 1.35 - 1.26 (m, 28H), 0.70 - 0.63 (m, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0227] [Example 10] [Synthesis of Compound U] Compound A (20 g) was mixed with THF (40 g), cooled to 0°C, and then a THF solution of (trimethylsilyl)methylmagnesium chloride (1.0 M, 61 mL) was added. The mixture was stirred at 60°C for 18 hours. Hydrochloric acid and hexane were then added for extraction. After removing the low-boiling point components under reduced pressure, compound U (11 g) was obtained by silica gel column chromatography (developing solvent: hexane / ethyl acetate). The structure of compound U was confirmed from the following NMR data.

[0228]

[0229] (NMR spectrum of compound U) 1 H-NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.7 Hz, 2H), 1.89 - 1.82 (m, 2H), 1.45-1.23 (m, 30H), 0.49 - 0.45 (m, 2H), 0.01 (s, 9H), -0.02 (s, 6H), -0.30 (s, 2H).

[0230] [Synthesis of Compound V] Compound U (11 g) was mixed with THF (10 g), cooled to 0°C, and then a THF solution of allyl magnesium chloride (2.0 M, 36 mL) was added. The mixture was stirred at room temperature for 18 hours. Hydrochloric acid and hexane were then added for extraction. After removing the low-boiling components under reduced pressure, compound V (10 g) was obtained by silica gel column chromatography (developing solvent: hexane / ethyl acetate). The structure of compound V was confirmed from the following NMR data.

[0231]

[0232] (NMR spectrum of compound V) 1 H-NMR (400 MHz, CDCl3) δ 5.81 (ddt, J = 17.0, 10.3, 6.8 Hz, 1H), 5.02 - 4.91 (m, 2H), 2.07 - 2.01 (m, 2H), 1.39 - 1.25 (m, 34H), 0.49 - 0.45 (m, 2H), 0.01 (s, 9H), -0.02 (s, 6H), -0.30 (s, 2H).

[0233] [Synthesis of Compound 1K] Compound 1K was obtained by following the same procedure as in the synthesis of Compound 1A, except that Compound V (1.0 g) was used instead of 18-(trifluoromethoxy)-1-octadecene. The structure of Compound 1K was confirmed from the following NMR data.

[0234]

[0235] (NMR spectrum of compound 1K) 1 H-NMR (400 MHz, CDCl3) δ 3.57 (s, 9H), 3.53 (s, 6H), 1.38 - 1.25 (m, 38H), 0.70 - 0.66 (m, 2H), 0.49 - 0.45 (m, 2H), 0.01 (s, 9H), -0.02 (s, 6H), -0.03 (s, 2H), -0.31 (s, 2H).

[0236] [Example 11] <Synthesis of Compound AA> 10-Undecenal (10 g) was mixed with aqueous formaldehyde solution (38% by mass, 47 g), ethanol (100 mL), and calcium oxide (4.7 g), and the mixture was stirred at 37°C for 24 hours. Then, the temperature was raised to 60°C and stirred for 2 hours. After the reaction, neutralization was performed using dry ice, and volatile components were removed by distillation under reduced pressure. Methylene chloride (100 g) was added to the crude solution, and insoluble components were removed using Celite. The separated organic phase was washed with saturated brine, dried with magnesium sulfate, and then the solvent and low-boiling point components were removed by distillation under reduced pressure. The obtained crude solution was purified by silica gel column chromatography (developing solvent: methylene chloride / methanol) to obtain 6.8 g of Compound AA. The structure of Compound AA was confirmed from the following NMR data.

[0237]

[0238] (NMR spectrum of compound AA) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.75 (d, J = 5.5 Hz, 6H), 2.44 (t, J = 5.5 Hz, 3H), 2.06 - 2.01 (m, 2H), 1.38 - 1.18 (m, 12H).

[0239] <Synthesis of Compound AB> Under a nitrogen atmosphere, compound AA (2.2 g), silver trifluoromethanesulfonate (37 g), cesium fluoride (26 g), Selectfluor® (registered trademark, manufactured by Tokyo Chemical Industry Co., Ltd., 20 g), 2-pyridine fluoride (12 mL), and dry toluene (100 mL) were added to a flask in a glove box and stirred at 25°C for 10 minutes. Then, (trifluoromethyl)trimethylsilane (21 mL) was added dropwise over 5 minutes while stirring, and the mixture was stirred at 25°C for a further 15 hours. The precipitate formed after the reaction was filtered off using Celite, the residue was washed with hexane, and the low-boiling point components of the obtained filtrate were removed under reduced pressure. The obtained crude solution was purified by silica gel column chromatography (eluent: hexane) to obtain 1.0 g of compound AB. The structure of compound AB was confirmed from the following NMR data.

[0240]

[0241] (NMR spectrum of compound AB) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.03 - 4.92 (m, 2H), 3.91 (s, 6H), 2.07 - 2.02 (m, 2H), 1.50 - 1.28 (m, 12H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0242] <Synthesis of Compound AC> Under a nitrogen atmosphere, 600 mg of compound AB was added to dry dichloromethane (5.0 mL) and zirconocene chloride hydride (400 mg), and the mixture was stirred at room temperature for 30 minutes. Then, 730 mg of N-bromosuccinimide was added to the solution, and the mixture was stirred at room temperature for another 30 minutes. The reaction was terminated with an aqueous sodium thiosulfate solution, and the organic phase was separated by adding hexane. The organic phase was washed with water and saturated brine, dried over magnesium sulfate, and then the solvent and low-boiling components were removed by vacuum distillation. The resulting crude solution was purified by silica gel column chromatography (developing solvent: hexane) to obtain 700 mg of compound AC. The structure of compound AC was confirmed from the following NMR data.

[0243]

[0244] (NMR spectrum of compound AC) 1 H-NMR (400MHz, CDCl3) δ 3.90 (s, 6H), 3.41 (t, J = 6.9 Hz, 2H), 1.89 - 1.82 (m, 2H), 1.50 - 1.28 (m, 14H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0245] <Synthesis of Compound AD> Under a nitrogen atmosphere, 18-bromo-1-octadecene (1.0 g) and magnesium (70 mg) were stirred in dry tetrahydrofuran (3.0 mL) for 1 hour, and the solid component was removed by filtration to obtain the corresponding Grignard reagent. Compound AC (700 mg) was dissolved in dry tetrahydrofuran (2.0 mL), copper(II) chloride (1.0 mg) was added, and the prepared Grignard reagent was added dropwise. The mixture was stirred at room temperature for 15 hours, and the reaction was terminated by adding aqueous ammonium chloride. Hexane was added to the mixture to separate the organic phase. The organic phase was washed with water and saturated brine, dried over magnesium sulfate, and the solvent and low-boiling components were removed by vacuum distillation. The resulting crude solution was purified by silica gel column chromatography (developing solvent: hexane) to obtain 620 mg of compound AD. The structure of compound AD was confirmed from the following NMR data.

[0246]

[0247] (NMR spectrum of compound AD) 1 H-NMR (400MHz, CDCl3) δ 5.81 (ddt, J = 17.2 Hz, 10.3 Hz, 6.7 Hz, 1H), 5.02 - 4.91 (m, 2H), 3.90 (s, 6H), 2.06 - 2.01 (m, 2H), 1.49 - 1.25 (m, 48H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0248] <Synthesis of Compound 1L> Except for using compound AD (620 mg) instead of 18-(trifluoromethoxy)-1-octadecene in the synthesis procedure for compound 1A, 430 mg of compound 1L was obtained using the same procedure. The structure of compound 1L was confirmed from the following NMR data.

[0249]

[0250] (NMR spectrum of 1 L of compound) 1 H-NMR (400MHz, CDCl3) δ3.90 (s, 6H), 3.57 (s, 9H), 3.53 (s, 6H), 1.49 - 1.25 (m, 48H), 0.70 - 0.66 (m, 2H), - 0.03 (s, 2H). 19 F-NMR (376MHz, CDCl3) δ-61.6.

[0251] [Example 12] <Synthesis of Compound AE> Under a nitrogen atmosphere, compound AC (500 mg), THF (2.0 g), and magnesium (28 mg) were added to a flask and stirred at room temperature for 2 hours. The reaction mixture was filtered to obtain the corresponding Grignard reagent. In another flask, 12-bromododecanoic acid (540 mg), THF (3.0 g), and a THF solution of methylmagnesium bromide (1.0 M, 1.0 mL) were added and stirred at 0°C for 15 minutes, and then copper(II) chloride (4.0 mg) was added to the same solution. Then, the other solution was added dropwise to the solution containing the copper salt and stirred at room temperature for 15 hours. After the reaction, hydrochloric acid and hexane were added for extraction, and the low-boiling point components were removed by distillation under reduced pressure. Compound AE (420 mg) was obtained by column chromatography using silica gel (developing solvent: hexane / ethyl acetate). The structure of compound AE was confirmed from the following NMR data.

[0252]

[0253] (NMR spectrum of compound AE) 1 H-NMR (400 MHz, CDCl3) δ 3.90 (s, 6H), 2.35 (t, J = 7.4 Hz, 2H), 1.67 - 1.60 (m, 2H), 1.47 - 1.25 (m, 36H).19 F-NMR (376MHz, CDCl3) δ-61.6.

[0254] <Synthesis of Compound AF> Under a nitrogen atmosphere, thionyl chloride (790 mg) was added to compound AE (420 mg) and the mixture was stirred at 80°C for 1 hour. Subsequently, the volatile components were removed by vacuum distillation to obtain the corresponding acid chlorides. Then, methylene chloride (5.0 g), triethylamine (100 mg), and 2-allylpent-4-ene-1-amine (100 mg) were added to the same vessel and the mixture was stirred at room temperature for 1 hour. After the reaction, hydrochloric acid and hexane were added for extraction, and low-boiling point components were removed by vacuum distillation. Compound AF (390 mg) was then obtained by column chromatography using silica gel (developing solvent: hexane / ethyl acetate). The structure of compound AF was confirmed from the following NMR data.

[0255]

[0256] (NMR spectrum of compound AF) 1 H-NMR (400 MHz, CDCl3) δ 5.84 - 5.74 (m, 2H), 5.42 (br, 1H), 5.09 - 5.03 (m, 4H), 3.90 (s, 6H), 3.23 - 3.20 (m, 2H), 2.17 - 2.01 (m, 6H), 1.77 - 1.70 (m, 1H), 1.63 - 1.57 (m, 2H), 1.32 - 1.24 (m, 36H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0257] <Synthesis of Compound 1M> Compound AF (390 mg) 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, 13 mg) and compound X (60% by mass, 480 mg) 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, 620 mg of compound 1M was obtained. The structure of compound 1M was confirmed from the following NMR data.

[0258]

[0259] (NMR spectrum of compound 1M) 1 H-NMR (400 MHz, CDCl3) δ 5.52 (brs, 1H), 3.90 (s, 6H), 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, 47H), 0.72 - 0.67 (m, 4H), -0.02 (s, 4H). 19 F-NMR (376MHz, CDCl3) δ-61.5.

[0260] [Example 13] Compound H1 was defined as the terminal trimethoxysilyl group-containing compound (9) described in Japanese Patent Publication No. 2024-114678.

[0261]

[0262] [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.

[0263] [Evaluation] The following evaluations were conducted using the obtained items. The results of the evaluation tests are shown in Table 1.

[0264] <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 oil contact angle is 53 degrees or higher. B: Average oil contact angle is 45 degrees or higher and less than 53 degrees. C: Average oil contact angle is less than 45 degrees.

[0265] <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 500 or more but less than 1000. C: Less than 500 rubs.

[0266]

[0267] As shown in Table 1, the compounds obtained in Examples 1 to 12 were confirmed to be able to form a surface layer with excellent oil repellency and abrasion resistance.

[0268] 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. 2It 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.

[0269] This application claims priority based on Japanese Patent Application No. 2025-041128, filed on 14 March 2025, and incorporates all of its disclosures herein.

[0270] 10 Substrate with undercoat 12 Substrate 14 Undercoat 20 Article 22 Surface layer

Claims

A compound comprising a group represented by the following formula (P) and a group represented by the following formula (Q). -Si(Y 1 )(Y 2 )-L} m -Si(Y 3 ( 3 (P) however, 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 are each independently a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, and Y 3 has at least one that is a hydrolyzable group or a hydroxyl group, L is - (CH 2 ) n - Or, if it is an oxygen atom, n is an integer of 1 or more, and m is an integer of 2 or more, then multiple Ls may be the same or different from each other. m is an integer greater than or equal to 1. (R Q ) n1 -L Q - (Q) however, R Q is, -OCF 3 , -SCF 3 , -SF 4 X 11 , -N(CF 3 ) X 12 ,-CHF 2 ien-CH 2 F, -C 6 F 5 , -C 8 F 7 , -Si(X 13 ) 3 , or -Ge(X 13 ) 3 X 11 is an alkyl group or a halogen atom, X 12 is an alkyl group, or -CF 3 and multiple X 13 Each of these is an alkyl group independently, L Q is a single bond or a (1+n1) valence group, n1 is an integer greater than or equal to 1, R Q If there are multiple R Q They may be identical or different from one another. The compound according to claim 1, represented by formula (1). (2) Q ) n1 -8 Q -8 1 -8 2 - (J 1 ) n2 (1) However, (R Q ) n1 -L Q - is a group represented by the above formula (Q), L 1 These are single bonds, or -O-, -C(=O)-, -C(=O)NX 14 -, -C(=O)O-, -NX 14 C(=O)-, -OC(=O)-, -NX 14 C(=O)NX 15 -, -NX 14 C(S)NX 15 -, -NX 14 C(=O)O-, -Si(X 14 ) 2 - A divalent hydrocarbon group which may have at least one group selected from the group consisting of a divalent organopolysiloxane residue and a divalent aromatic heterocycle, and if the divalent hydrocarbon group includes a cyclic hydrocarbon group, the cyclic hydrocarbon group may have substituents. X 14 and X 15 Each of these is independently a hydrogen atom or an alkyl group, L 2 This is a single bond or a group with three or more (1+n2) valencies. J 1 This is a group represented by the above formula (P), n2 is an integer greater than or equal to 1, If n2 is 1, L 2 It is a single bond, J 1 If there are multiple J 1 They may be identical or different from one another.   The compound according to claim 2, wherein n2 is 1 or 2 in formula (1).   A surface treatment agent comprising the compound described in any one of claims 1 to 3.   The surface treatment agent according to claim 4, further comprising a liquid medium. The surface treatment agent according to claim 4, which is an antifouling coating agent or a waterproof coating agent. The surface treatment agent according to claim 5, which is a stain-resistant coating agent or a waterproof coating agent.   An article having a surface layer formed using a compound according to any one of claims 1 to 3 on the surface of a substrate.   The article according to claim 8, which is an optical component.   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.   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.   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.   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.