WO2023204020A1

WO2023204020A1 - Compound, composition, surface treating agent, method for producing article, and article

Info

Publication number: WO2023204020A1
Application number: PCT/JP2023/013997
Authority: WO
Inventors: 愛理榊原; 雄二郎富塚; 元志青山; 弘毅渡邉
Original assignee: Ａｇｃ株式会社
Priority date: 2022-04-19
Filing date: 2023-04-04
Publication date: 2023-10-26

Abstract

Provided are: a compound that contains a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms, at least one partial structure selected from the group consisting of (A) a linear alkynene group having 17 or more carbon atoms, (B) -CH=CH- and (C) a substituted or unsubstituted bivalent aromatic ring group having 4 to 16 carbon atoms, and a reactive silyl group; a composition and a surface treating agent each containing the compound; and an article and a method for producing an article, in each of which the surface treating agent is used.

Description

Compounds, compositions, surface treatment agents, methods for producing articles, and articles

The present disclosure relates to compounds, compositions, surface treatment agents, methods of manufacturing articles, and articles.

In recent years, in order to improve performance such as appearance and visibility, there has been a demand for technology that makes it difficult for fingerprints to form on the surface of articles and technology that makes it easier to remove dirt. As a specific method, a method is known in which the surface of an article is subjected to surface treatment using a surface treatment agent. For example, Patent Document 1 describes a surface treatment agent containing an organosilane compound having a phenyl group. Further, Patent Document 2 describes a coating composition containing a silane compound having a specific structure having an aromatic ring.

International Publication No. 2020/026729 International Publication No. 2021/219532

On the other hand, surface treatment agents are required to be further improved from the viewpoint of wear resistance and the like. In view of this situation, the present disclosure relates to a compound capable of imparting good wear resistance to a substrate, a composition and a surface treatment agent containing the compound, and an article using the surface treatment agent and a method for manufacturing the article.

Means for solving the above problems include the following aspects.
<1> A monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms;
(A) a linear alkylene group having 17 or more carbon atoms; (B) -CH=CH-; and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. at least one substructure comprising;
a reactive silyl group,
Compounds containing.
<2> The compound according to <1>, wherein the aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group is a benzene ring, a naphthalene ring, or a pyridine ring.
<3> The aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group has 1 to 15 substituents, and each of the substituents independently has a halogen atom, a hydroxyl group, or a carbon number 1 to 10. alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, -OCF ₃ , -SF ₅ , -OC(O)R ^s , -N(R ^s )C(O)R ^s , -NO ₂ , -SO ₂ R ^s , -NR ^s ₂ , -C(O)OR ^s , -C(O)NR ^s ₂ , and -C(O)R ^s , where , R ^s are each independently a hydrogen atom or an alkyl group, the compound according to <1> or <2>.
<4> Compound represented by the following formula (1):
Ar-Z-Y ¹ [-Si(R) _n L _3-n ] _g ...(1)
In formula (1),
Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms,
Z is a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. A divalent group containing at least one partial structure selected from
Y ¹ is a single bond when g is 1, and is a (g + 1) valent linking group when g is 2 or more,
R is each independently a monovalent hydrocarbon group,
L is each independently a hydrolyzable group or a hydroxyl group,
n is an integer from 0 to 2,
g is an integer of 1 or more.
<5> The compound according to <4>, wherein in formula (1), g is an integer of 2 or more.
<6> The compound according to <4> or <5>, wherein the aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group is a benzene ring, a naphthalene ring, or a pyridine ring.
<7> The aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group has 1 to 15 substituents, and each of the substituents independently has a halogen atom, a hydroxyl group, a carbon number 1 to 10 alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, -OCF ₃ , -SF ₅ , -OC(O)R ^s , -N(R ^s )C(O)R ^s , -NO ₂ , -SO ₂ R ^s , -NR ^s ₂ , -C(O)OR ^s , -C(O)NR ^s ₂ , and -C(O)R ^s , where , R ^s are each independently a hydrogen atom or an alkyl group, the compound according to any one of <4> to <6>.
<8> Compound represented by the following formula (1-1):
Ar-Z-Y ¹¹ (D) _g1 ...(1-1)
In formula (1-1),
Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms,
Z is a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. A divalent group containing at least one partial structure selected from
^Y11 is a single bond when g1 is 1, and is a (g1+1) valent linking group when g1 is 2 or more,
Each D is independently -Q ^L -CH=CH ₂ , where Q ^L is a single bond or a divalent linking group,
g1 is an integer of 1 or more.
<9> A composition comprising the compound according to any one of <1> to <7> and a liquid medium. <10> A surface treatment agent comprising the compound according to any one of <1> to <7>.
<11> The surface treatment agent according to <10>, further comprising a liquid medium.
<12> A method for manufacturing an article, comprising performing a surface treatment on a base material using the surface treatment agent described in <10> or <11> to manufacture an article in which a surface treatment layer is formed on the base material. .
<13> An article comprising a base material and a surface treatment layer disposed on the base material and surface treated with the surface treatment agent according to <10>.
<14> The article according to <13>, wherein the article is an optical member.
<15> The article according to <14>, wherein the article is a display or a touch panel.

According to the present disclosure, there are provided a compound that can impart good wear resistance to a substrate, a composition and a surface treatment agent containing the compound, and an article and a method for manufacturing the article using the surface treatment agent.

Hereinafter, modes for carrying out embodiments of the present disclosure will be described in detail. However, the embodiments of the present disclosure are not limited to the following embodiments. In the following embodiments, the constituent elements (including elemental steps and the like) are not essential unless otherwise specified. The same applies to numerical values and their ranges, and they do not limit the embodiments of the present disclosure.

In this disclosure, the term "step" includes not only a step that is independent from other steps, but also a step that cannot be clearly distinguished from other steps, as long as the purpose of the step is achieved. .
In the present disclosure, numerical ranges indicated using "~" include the numerical values written before and after "~" as minimum and maximum values, respectively.
In the present disclosure, each component may contain multiple types of corresponding substances. If there are multiple types of substances corresponding to each component in the composition, the content rate or content of each component is the total content rate or content of the multiple types of substances present in the composition, unless otherwise specified. means quantity.
In this disclosure, the term "layer" or "film" refers to the case where the layer or film is formed only in a part of the region, in addition to the case where the layer or film is formed in the entire region when observing the region where the layer or film is present. This also includes cases where it is formed.
In the present disclosure, the term "surface treated layer" refers to a layer formed on the surface of a base material by surface treatment.
In the present disclosure, when a compound or group is represented by a specific formula (X), the compound or group represented by the formula (X) may be referred to as a compound (X) and a group (X), respectively.
In the present disclosure, the carbon number X in the expression "an aromatic ring group having carbon number X" represents the carbon number of the atomic group constituting the ring, and does not include the carbon number of the substituent.
In the present disclosure, a (poly)oxyalkylene group means an oxyalkylene group or a polyoxyalkylene group.

[Compound]
The compound of the present disclosure comprises a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms, (A) a linear alkylene group having 17 or more carbon atoms, and (B) -CH=CH- , and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms, and a reactive silyl group. Hereinafter, "a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms" will also be referred to as a "specific aromatic ring group". In addition, "a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms,""at least one partial structure selected from the above" is also comprehensively referred to as a "specific partial structure".
It has been surprisingly found that when the surface of a substrate is treated with a composition containing the compound of the present disclosure, the surface of the substrate has excellent wear resistance. Although the reason for this is not clear, it is presumed that one reason is that the specific partial structure contributes to the orientation of the molecules, resulting in good wear resistance when the surface treatment layer is formed.

In the compound of the present disclosure, the specific aromatic ring group and the reactive silyl group are present at the end of the compound. The specific partial structure is preferably present inside the compound, and between the specific aromatic ring group and the reactive silyl group. The specific partial structure may be directly bonded to each of the specific aromatic ring group and the reactive silyl group, or may be bonded to each of the specific aromatic ring group and the reactive silyl group via a linking group. Therefore, the compound of the present disclosure is preferably a compound in which a specific aromatic ring group, a specific partial structure, and a reactive silyl group are bonded in this order directly or via a linking group.

The monovalent aromatic ring group in the specific aromatic ring group means a monovalent group obtained by removing one hydrogen atom from an aromatic ring. In addition, when multiple aromatic rings are connected via a single bond or a linking group, such as a biphenyl group, phenylmethylphenyl group, or phenoxyphenyl group, the monovalent group that is the terminal aromatic ring is used as the compound of the present disclosure. It shall be classified as a specific aromatic ring group.
The aromatic ring in the specific aromatic ring group may be an aromatic hydrocarbon ring or an aromatic heterocycle, and from the viewpoint of excellent water repellency and lipophilicity, an aromatic hydrocarbon ring that does not contain a hetero atom is preferred. preferable.
The aromatic ring in the specific aromatic ring group may be a monocyclic ring or a condensed polycyclic ring.
The specific aromatic ring group preferably has 5 to 10 carbon atoms, more preferably 6 to 8 carbon atoms.

The aromatic rings include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, an indene ring, an azulene ring, a fluorene ring, a pyrene ring; a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring. , an indole ring, a purine ring, a quinoline ring, an isoquinoline ring, a chromene ring, a phenothiazine ring, a phenoxazine ring, an acridine ring, a phenazine ring, a carbazole ring, and the like. From the viewpoint of improving water repellency and lipophilicity, benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, indene rings, azulene rings, and fluorene rings are preferred. From the viewpoint of availability of raw materials, benzene rings, naphthalene rings, and pyridine rings are preferred, benzene rings and naphthalene rings are more preferred, and benzene rings are even more preferred.

The aromatic ring may or may not have a substituent. When the aromatic ring has a substituent, the number of substituents may be 1 to 15, preferably 1 to 9, and more preferably 1 to 7. Examples of substituents include halogen atoms, hydroxyl groups, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, -OCF ₃ , -SF ₅ , -OC(O) R ^s , -N(R ^s )C(O)R ^s , -NO ₂ , -SO ₂ R ^s , -NR ^s ₂ , -C(O)OR ^s , -C(O)NR ^s ₂ , -C (O)Rs ^etc. are mentioned. Here, each R ^s is independently a hydrogen atom or an alkyl group (preferably 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably a methyl group). In one embodiment, the substituent is preferably a substituent that does not contain a halogen atom (for example, a fluorine atom), such as a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -OC(O) R ^s , -N(R ^s )C(O)R ^s , -NO ₂ , -SO ₂ R ^s , -NR ^s ₂ , -C(O)OR ^s , -C(O)NR ^s ₂ , and - C(O) ^Rs is more preferred. In one embodiment, from the viewpoint of excellent water repellency and lipophilicity, the substituent is preferably a substituent that does not contain a hetero atom (eg, an oxygen atom, a nitrogen atom, and a sulfur atom), and an alkyl group is preferable. In one embodiment, from the viewpoint of excellent water repellency and lipophilicity, it is preferable that the aromatic ring has no substituent. When the aromatic ring has a plurality of substituents, each substituent may be the same or different from each other.

The number of specific aromatic ring groups in the compound of the present disclosure may be one or more, and is preferably one. When the compound of the present disclosure contains a plurality of specific aromatic ring groups, each specific aromatic ring group may be the same or different from each other.

The specific partial structure is selected from the following structures.
(A) Straight chain alkylene group having 17 or more carbon atoms (hereinafter also referred to as "specific partial structure A").
(B) -CH=CH- (hereinafter also referred to as "specific partial structure B").
(C) Substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms (hereinafter also referred to as "specific partial structure C").

The compound of the present disclosure may contain any one specific partial structure, or may contain two or more specific partial structures. When the compound of the present disclosure contains two or more specific partial structures, each specific partial structure may be the same or different from each other. "The compound of the present disclosure includes two or more specific partial structures" means that the compound of the present disclosure includes two or more specific partial structures A, two or more specific partial structures B, and the specific partial structure C. Examples include cases in which two or more of the specific partial structures A to C are included, and cases in which any combination of specific partial structures A to C is included.

The linear alkylene group in specific partial structure A means an unsubstituted linear alkylene group.
The number of carbon atoms in the specific partial structure A is preferably 18 or more from the viewpoint of improving water repellency. From the viewpoint of ease of manufacture, the carbon number is preferably 36 or less, more preferably 28 or less, and even more preferably 24 or less. From this point of view, the number of carbon atoms is preferably 17 to 36, more preferably 18 to 28, and even more preferably 18 to 24. The number of carbon atoms may be 21 or more.

Specific partial structure B is -CH=CH-. In one embodiment, a plurality of specific partial structures B may be adjacent to each other to form a conjugated double bond. In one embodiment, the plurality of specific partial structures B do not need to form a conjugated double bond.
The specific partial structure B may be either cis or trans, and preferably trans.
The position of the specific partial structure B in the compound is not particularly limited. In one embodiment, the specific partial structure B is preferably located adjacent to the specific aromatic ring group (ie, -CH═CH- is directly bonded to the aromatic ring of the specific aromatic ring group). This expands the conjugated structure of the specific aromatic ring group, so it is thought that better lipophilicity and lower fingerprint visibility are exhibited.

The specific partial structure C is a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. The divalent aromatic ring group in the specific partial structure C means a divalent group obtained by removing two hydrogen atoms from an aromatic ring.
The position of the specific partial structure C in the compound is not particularly limited, and the specific partial structure C may or may not be adjacent to a specific aromatic ring group, and may or may not be adjacent to a reactive silyl group. In one embodiment, the aromatic ring is preferably located adjacent to the specific aromatic ring group. This expands the conjugated structure of the specific aromatic ring group, so it is thought that better lipophilicity and lower fingerprint visibility are exhibited.

The substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms in the specific partial structure C includes the aromatic rings exemplified as the aromatic ring in the specific aromatic ring group. From the viewpoint of improving water repellency and lipophilicity, benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, indene rings, azulene rings, and fluorene rings are preferred. From the viewpoint of excellent raw material availability, benzene rings, naphthalene rings, and pyridine rings are preferred, benzene rings and naphthalene rings are more preferred, and benzene rings are even more preferred.

The aromatic ring may or may not have a substituent. When the aromatic ring has a substituent, the number of substituents may be 1 to 14, preferably 1 to 8, and more preferably 1 to 6. Examples of the substituent include the substituents exemplified as substituents that the aromatic ring in the specific aromatic ring group may have. In one embodiment, from the viewpoint of excellent water repellency and lipophilicity, the substituent is preferably a substituent that does not contain a hetero atom (eg, an oxygen atom, a nitrogen atom, and a sulfur atom), and an alkyl group is preferable. In one embodiment, from the viewpoint of excellent water repellency and lipophilicity, it is preferable that the aromatic ring has no substituent. When the aromatic ring has a plurality of substituents, each substituent may be the same or different from each other.

A reactive silyl group means a group in which a reactive group is bonded to a Si atom. The reactive group is preferably a hydrolyzable group or a hydroxyl group.

Hydrolyzable is a group that becomes a hydroxyl group through a hydrolysis reaction. That is, the hydrolyzable silyl group represented by Si-L becomes a silanol group represented by Si-OH through a hydrolysis reaction. The silanol groups further react among themselves to form Si--O--Si bonds. Further, the silanol group can undergo a dehydration condensation reaction with a silanol group derived from an oxide present on the surface of the base material to form a Si--O--Si bond. Examples of the hydrolyzable group include an alkoxy group, an aryloxy group, a halogen atom, an acyl group, an acyloxy group, and an isocyanato group (-NCO). The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms. However, the aryl group of the aryloxy group includes a heteroaryl group. The halogen atom is preferably a chlorine atom. The acyl group is preferably an acyl group having 1 to 6 carbon atoms. The acyloxy group is preferably an acyloxy group having 1 to 6 carbon atoms.

From the viewpoint of easy production of a uniform film and excellent durability, the reactive silyl group is preferably an alkoxysilyl group or a trichlorosilyl group. From the viewpoint of ease of handling by-products generated in the reaction with the base material, the reactive silyl group is more preferably an alkoxysilyl group. The alkoxysilyl group is preferably a dialkoxysilyl group or a trialkoxysilyl group, and more preferably a trialkoxysilyl group.

The number of reactive silyl groups that the compound of the present disclosure has is one or more. In one embodiment, the number of reactive silyl groups is preferably 1 to 15, more preferably 1 to 6, from the viewpoint of the surface treatment layer having excellent abrasion resistance and fingerprint removability. In one embodiment, from the viewpoint of excellent wear resistance of the surface treatment layer, the number of reactive silyl groups is preferably 2 or more, more preferably 2 to 4, and even more preferably 2 or 3. preferable. In one embodiment, from the viewpoint of excellent fingerprint removability of the surface treatment layer, the number of reactive silyl groups is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. preferable.

As the reactive silyl group, a group represented by the following formula (2) is preferable.
-Si(R) _n L _3-n ...(2)
In formula (2), R is each independently a monovalent hydrocarbon group, L is each independently a hydrolyzable group or a hydroxyl group, and n is an integer from 0 to 2.

When there are multiple groups (2) in one molecule, the multiple groups (2) may be the same or different. From the viewpoint of excellent availability of raw materials and ease of manufacturing the compound, it is preferable that the plurality of groups (2) are the same.

Each R is independently a monovalent hydrocarbon group, preferably a monovalent saturated hydrocarbon group. The number of carbon atoms in R is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.

When L is a hydrolyzable group, the hydrolyzable group is preferably the one described above.

Among these, L is preferably an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms) or a halogen atom from the viewpoint of ease of manufacturing the compound. L is preferably an alkoxy group having 1 to 4 carbon atoms, from the viewpoint of less outgassing during coating and better storage stability of the compound. When long-term storage stability of the compound is required, L is more preferably an ethoxy group. When the reaction time after coating is to be shortened, L is more preferably a methoxy group. In formula (2), at least one L is preferably the above group, and more preferably all L are the above groups.

n is an integer of 0 to 2, preferably 0 or 1, and more preferably 0. When the compound of the present disclosure is used as a surface treatment agent, the presence of a plurality of L's makes the adhesion of the surface treatment layer to the base material stronger.
When n is 1 or less, the plurality of L's present in one molecule may be the same or different from each other. From the viewpoint of excellent availability of raw materials and ease of manufacturing the compound, it is preferable that the plurality of L's are the same. When n is 2, multiple R's present in one molecule may be the same or different from each other. From the viewpoint of excellent availability of raw materials and ease of manufacturing the compound, it is preferable that a plurality of R's are the same.

The specific partial structure may be bonded to the specific aromatic ring group and the reactive silyl group directly or via a linking group. As the linking group that connects the specific partial structure and the specific aromatic ring group, "a divalent linking group that may exist between the specific partial structure and Ar" in Z in formula (1) described below is Can be mentioned. As the linking group that connects the specific partial structure and the reactive silyl group, "existing between the specific partial structure and Y ¹ [-Si(R) _n L _3-n ] _g " in formula (1) described below is used. (g+1)-valent linking group represented by Y ¹ , and combinations thereof. The linking group that connects the specific partial structure and the reactive silyl group may or may not have an organosiloxane residue.
When the compound of the present disclosure contains two or more specific partial structures, the two or more specific partial structures may be bonded directly or via a linking group. Examples of the linking group that connects specific partial structures include "a divalent linking group that may exist between a plurality of specific partial structures" in Z in formula (1) described below. The linking group that connects the specific partial structures may or may not have an organosiloxane residue.

The compound of the present disclosure may or may not contain a halogen atom (for example, a fluorine atom). In one embodiment, from the viewpoint of reducing environmental impact, the compound of the present disclosure preferably does not contain a halogen atom (eg, a fluorine atom).

The compound of the present disclosure may or may not have an organosiloxane residue.

The compound of the present disclosure is preferably a compound represented by the following formula (1) from the viewpoint of excellent wear resistance.
Ar-Z-Y ¹ [-Si(R) _n L _3-n ] _g ...(1)
In formula (1),
Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms,
Z is a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. A divalent group containing at least one partial structure selected from
Y ¹ is a single bond when g is 1, and is a (g + 1) valent linking group when g is 2 or more,
R is each independently a monovalent hydrocarbon group,
L is each independently a hydrolyzable group or a hydroxyl group,
n is an integer from 0 to 2,
g is an integer of 1 or more.

In formula (1), Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms. Details of Ar are the same as those of the specific aromatic ring group described above.

Z is from the group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. It is a divalent group containing at least one selected partial structure. (A) to (C) have the same meanings as the above-mentioned specific partial structures A to C, respectively.
Z may include any one specific partial structure, or may include two or more specific partial structures. When Z includes two or more specific partial structures, the specific partial structures may be the same or different from each other. Cases in which "Z includes two or more specific substructures" include cases where Z includes two or more specific substructures A, two or more specific substructures B, and two or more specific substructures C. , and any combination of specific partial structures A to C.

The specific partial structure in Z and Ar may be bonded directly or may be bonded via a divalent linking group.
The specific partial structure in Z and Y ¹ [-Si(R) _n L _3-n ] _g may be directly bonded or may be bonded via a divalent linking group.
When Z contains two or more specific partial structures, the plurality of specific partial structures may be directly bonded or may be bonded via a divalent linking group.
However, any of the above-mentioned "divalent linking groups" in Z does not include a specific partial structure. Further, it is assumed that no alkylene group in the "bivalent linking group" is adjacent to the specific partial structure A.
Z may or may not have an organosiloxane residue.

Divalent linking groups that may exist between the specific partial structure and Ar include -O-, -S-, -SO ₂ -, -N(R ^d )-, -C(O)- , -Si(R ^a ) ₂ -, and combinations thereof; divalent hydrocarbon groups; divalent organopolysiloxane residues; and combinations thereof. The above R ^a is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group. The R ^d is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
Examples of the divalent hydrocarbon group include a saturated hydrocarbon group and an unsaturated hydrocarbon group. The divalent hydrocarbon group may be linear, branched, or cyclic. Examples of the divalent hydrocarbon group include an alkylene group and an alkynylene group. The alkylene group preferably has 1 to 16 carbon atoms, and the alkynylene group preferably has 2 to 20 carbon atoms.
The combinations of -O-, -S-, -SO ₂ -, -N(R ^d )-, -C(O)-, and -Si(R ^a ) ₂ - include -OC(O)-, -C(O)O-, -C(O)N(R ^d )-, -N(R ^d )C(O)-, -N(R ^d )C(O)N(R ^d )-, - Examples include N(R ^d )C(O)O-, -OC(O)N(R ^d )-, -SO ₂ N(R ^d )-, -N(R ^d )SO ₂ -, and the like.
In one embodiment, the divalent linking group includes an alkylene group having 1 to 16 carbon atoms, -OC(O)-, -O-, -N(R ^d )C(O)-, -NR ^d -, -S-, -SC(O)-, and combinations thereof are preferred.

The divalent linking group that may exist between the specific partial structure in Z and Y ¹ [-Si(R) _n L _3-n ] _g is the divalent linking group that exists between the specific partial structure and Ar. Examples of the divalent linking group that may be used include those mentioned above.
In one embodiment, the divalent linking group includes an alkylene group having 1 to 16 carbon atoms; and -OC(O)-, -C(O)O-, -C(O)N(R ^d )- , -N(R ^d )C(O)-, and combinations of these with an alkylene group having 1 to 16 carbon atoms are preferred.

Examples of the divalent linking group that may exist between a plurality of specific partial structures include those mentioned above as the divalent linking group that may exist between the specific partial structure and Ar.
In one embodiment, the divalent linking group includes an alkylene group having 1 to 16 carbon atoms, -OC(O)-, -O-, -N(R ^d )C(O)-, -NR ^d -, -S-, -SC(O)-, and combinations thereof are preferred.
When Z contains a plurality of the divalent linking groups, the plurality of divalent linking groups may be the same or different from each other.

In formula (1), Y ¹ is a single bond when g is 1, and is a (g+1)-valent linking group when g is 2 or more.
The (g+1)-valent linking group represented by Y ¹ includes a hydrocarbon group; a carbon atom, a nitrogen atom, a silicon atom, a cyclic group, and a di- to octa-valent organopolysiloxane residue; and combinations thereof. Can be mentioned. The above R ^a is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group. The R ^d is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
Examples of the hydrocarbon group include a saturated hydrocarbon group and an unsaturated hydrocarbon group. The hydrocarbon group may be linear, branched, or cyclic. Hydrocarbon groups include alkylene groups and alkynylene groups. The alkylene group preferably has 1 to 16 carbon atoms, and the alkynylene group preferably has 2 to 20 carbon atoms. The hydrocarbon group has -O-, -S-, -SO ₂ -, -N(R ^d )-, -C(O)-, -Si(R ^a ) ₂ -, Or you may have a combination of these.
The combinations of -O-, -S-, -SO ₂ -, -N(R ^d )-, -C(O)-, and -Si(R ^a ) ₂ - include -OC(O)-, -C(O)O-, -C(O)N(R ^d )-, -N(R ^d )C(O)-, -N(R ^d )C(O)N(R ^d )-, - Examples include N(R ^d )C(O)O-, -OC(O)N(R ^d )-, -SO ₂ N(R ^d )-, -N(R ^d )SO ₂ -, and the like.
As Y ¹ , Si(R) _n L _3-n is excluded from formula (3-1A), formula (3-1B), and formulas (3-1A-2) to (3-1A-7) described later. Other groups may also be mentioned.
Y ¹ may be groups (g2-1) to (g2-13) described below.

In formula (1), the details of [-Si(R) _n L _3-n ] are the same as the details of group (2) described above. When compound (1) has a plurality of [-Si(R) _n L _3-n ], the plurality of [-Si(R) _n L _3-n ] may be the same or different from each other. .

In formula (1), g is an integer of 1 or more. In one embodiment, g is preferably from 1 to 15, more preferably from 1 to 6, from the viewpoint of the abrasion resistance and fingerprint removability of the surface treatment layer. In one embodiment, g is preferably 2 or more, more preferably 2 to 4, and even more preferably 2 or 3 from the viewpoint of excellent wear resistance of the surface treatment layer. In one embodiment, g is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1 from the viewpoint of excellent fingerprint removability of the surface treatment layer.

The group represented by Y ¹ [-Si(R) _n L _3-n ] _g in formula (1) is [-Si(R) _n L _3-n ], the group (3-1A), or the group (3-1B) is preferred.

-X ³¹ (-Q ^b -Si(R) _n L _3-n ) _h (-R ³¹ ) _i ...(3-1A)
-[C(R ³² )(-Q ^d -Si(R) _n L _3-n )-CH ₂ -] _y -C(R ³² )(R ³³ )(-Q ^d -Si(R) _n L _{3 -n} ) …(3-1B)

In formula (3-1A),
X ³¹ is a carbon atom, a nitrogen atom, a silicon atom, a di- to octavalent organopolysiloxane residue, or a group having a (h+i+1)-valent ring;
Q ^b is a single bond or a divalent linking group,
R ³¹ is a hydrogen atom, a hydroxyl group or an alkyl group,
h is an integer of 2 or more, i is an integer of 0 or more,
The definitions and specific examples of R, L, and n are the same as the definitions and specific examples of each symbol in the reactive silyl group.

In formula (3-1B),
R ³² is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms,
Q ^d is a single bond or an alkylene group,
R ³³ is a hydrogen atom or a halogen atom,
y is an integer from 2 to 10,
The definitions and specific examples of R, L, and n are the same as the definitions and specific examples of each symbol in the reactive silyl group.

X ³¹ is a carbon atom, a nitrogen atom, a silicon atom, a 2- to 8-valent organopolysiloxane residue, or a group having a (h+i+1)-valent ring.
Examples of the divalent to octavalent organopolysiloxane residues include divalent organopolysiloxane residues and (w2+1)-valent organopolysiloxane residues described below.

When X ³¹ is a group having a (h+i+1)-valent ring, Z, (-Q ^b -Si(R) _n L _3-n ), and -R ³¹ (when i=1 or more) represent the ring. It is directly bonded to its constituent atoms. However, the ring is a ring other than an organopolysiloxane ring. Hereinafter, unless otherwise specified, the ring in X ³¹ means a ring other than an organopolysiloxane ring.
The ring in X ³¹ may be a monocyclic ring, a fused polycyclic ring, a bridged ring, a spiro ring, or an assembled polycyclic ring, and the atoms constituting the ring may be a carbocyclic ring consisting only of carbon atoms, or a divalent ring. A heterocycle consisting of a heteroatom having the above valence and a carbon atom may also be used. Further, the bond between atoms constituting the ring may be a single bond or a multiple bond. Furthermore, the ring may be an aromatic ring or a non-aromatic ring.
The monocyclic ring is preferably a 4- to 8-membered ring, more preferably a 5-membered ring or a 6-membered ring. The fused polycyclic ring is preferably a fused polycyclic ring in which two or more 4- to 8-membered rings are fused together, and fused polycyclic rings in which 2 or 3 rings selected from 5-membered rings and 6-membered rings are bonded together; A fused polycyclic ring in which one or two rings selected from membered rings and six-membered rings and one four-membered ring are bonded is more preferred. The bridged ring is preferably a bridged ring whose largest ring is a 5- or 6-membered ring, and the spiro ring is preferably a spiro ring consisting of two 4- to 6-membered rings. As a collective polycyclic ring, two or three rings selected from 5-membered rings and 6-membered rings are bonded via a single bond, 1 to 3 carbon atoms, or 1 heteroatom with a valence of 2 or 3. A set of polycyclic rings is preferred. In addition, in the set polycycle, it is preferable that each ring is bonded with either Z, (-Q ^b -Si(R) _n L _3-n ), or R ³¹ (when i=1 or more) .
The hetero atoms constituting the ring are preferably nitrogen atoms, oxygen atoms, and sulfur atoms, and more preferably nitrogen atoms and oxygen atoms. The number of heteroatoms constituting the ring is preferably 3 or less. Furthermore, when the number of heteroatoms constituting the ring is two or more, these heteroatoms may be the same or different.

The ring in X ³¹ is a 3- to 8-membered aliphatic ring, a benzene ring, a 3- to 8-membered aliphatic ring, from the viewpoint of easy production of the compound, and from the viewpoint of further improving the abrasion resistance, light resistance, and chemical resistance of the surface treatment layer. 8-membered heterocycles, fused rings in which two or three of these rings are fused together, bridged rings in which the largest ring is a 5- or 6-membered ring, and two of these rings One type selected from the group consisting of an aggregated polycyclic ring having the above and whose connecting group is a single bond, an alkylene group having 3 or less carbon atoms, an oxygen atom or a sulfur atom is preferable.
Preferred rings include a benzene ring, a 5- or 6-membered aliphatic ring, a 5- or 6-membered heterocycle having a nitrogen atom or an oxygen atom, and a 5- or 6-membered carbon ring and a 4- to 6-membered heterocycle. It is a fused ring with a ring.
Specific rings include the rings shown below, 1,3-cyclohexadiene ring, 1,4-cyclohexadiene ring, anthracene ring, cyclopropane ring, decahydronaphthalene ring, norbornene ring, norbornadiene ring, furan ring, Examples include a pyrrole ring, a thiophene ring, a pyrazine ring, a morpholine ring, an aziridine ring, an isoquinoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an imidazole ring, a pyrazole ring, a pyran ring, a pyridazine ring, a pyrimidine ring, and an indene ring. In addition, below, a ring having an oxo group (=O) is also shown.

The bond _that ^does _not constitute a ring of the atom that constitutes the ^ring ⁱⁿ If there are any remaining bonds, they are bonded to hydrogen atoms or substituents. Examples of the substituent include a halogen atom, an alkyl group (which may contain an etheric oxygen atom between carbon atoms), a cycloalkyl group, an alkenyl group, an allyl group, an alkoxy group, and an oxo group (=O). etc.
In addition, one carbon atom constituting the ring has two bonds that can be bonded to Z, (-Q ^b -Si(R) _n L _3-n ), or -R ³¹ (when i = 1 or more). If it has, any two of Z, (-Q ^b -Si(R) _n L _3-n ), and -R ³¹ may be bonded to that one carbon atom. It is preferable that Z and Q ^b are bonded to different ring constituent atoms. Each of the i R ^31s may be bonded to a separate ring atom, or two of the i R ^31s may be bonded to one ring carbon atom. There may be two or more ring-constituting carbon atoms to which two R ^31s are bonded.

Among these, X ³¹ is a group having a carbon atom, a nitrogen atom, a silicon atom, a 4- to 8-valent organopolysiloxane residue, or a (h+i+1)-valent ring, from the viewpoint of improving the abrasion resistance of the surface treatment layer. is preferable, and carbon atom is more preferable.

Q ^b is a single bond or a divalent linking group.
Examples of divalent linking groups include divalent hydrocarbon groups, divalent heterocyclic groups, -O-, -S-, -SO ₂ -, -N(R ^d )-, -C(O) -, -Si(R ^a ) ₂ -, and a combination of two or more thereof. The above R ^a is an alkyl group (preferably having 1 to 10 carbon atoms) or a phenyl group. The above R ^d is a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
Examples of divalent hydrocarbon groups include saturated hydrocarbon groups and unsaturated hydrocarbon groups. The hydrocarbon group may be linear, branched, or cyclic. Hydrocarbon groups include alkylene groups and alkynylene groups. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 2 to 20 carbon atoms, such as 2, 3, 8, 9, and 11 carbon atoms. The alkynylene group preferably has 2 to 20 carbon atoms, such as 2, 3, 8, 9, and 11 carbon atoms.
Examples of groups combining two or more of the above-mentioned types include -OC(O)-, -C(O)O-, -C(O)S-, -C(O)N(R ^d )-, - N(R ^d )C(O)-, -N(R ^d )C(O)N(R ^d )-, -N(R ^d )C(O)O-, -OC(O)N(R ^d )-, -SO ₂ N(R ^d )-, -N(R ^d )SO ₂ -, a combination of these and an alkylene group, and the like.
In one embodiment, Q ^b is preferably a single bond or an alkylene group.

R ³¹ is a hydrogen atom, a hydroxyl group or an alkyl group.
The number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.

h is an integer of 2 or more, and i is an integer of 0 or more.
When X ³¹ is a nitrogen atom, h is 2 and i is 1.
When X ³¹ is a carbon atom or a silicon atom, h is 2 or 3, i is 0 or 1, and h+i=3 is satisfied.
When X ³¹ is a divalent to octavalent organopolysiloxane residue, h is an integer of 2 to 7, i is an integer of 0 to 5, and h+i=1 to 7 is satisfied.
When X ³¹ is a group having a (h+i+1)-valent ring, h is an integer of 2 to 7, i is an integer of 0 to 5, and h+i=1 to 7 is satisfied.
Two or more (-Q ^b -Si(R) _n L _3-n ) may be the same or different. When there are two or more R ³¹ s, two or more (-R ³¹ )s may be the same or different.

Among these, i is preferably 0 from the viewpoint of improving the wear resistance of the surface treatment layer.

R ³² is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and is preferably a hydrogen atom from the viewpoint of easy production of the compound.
As the alkyl group, a methyl group is preferred.

Q ^d is a single bond or an alkylene group. The alkylene group preferably has 1 to 16 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms. From the viewpoint of easy production of the compound, Q ^d is preferably a single bond or -CH ₂ -.

R ³³ is a hydrogen atom or a halogen atom, and is preferably a hydrogen atom from the viewpoint of easy production of the compound.

y is an integer from 2 to 10, preferably from 2 to 6.
Two or more [C(R ³² )(-Q ^d -Si(R) _n L _3-n )-CH ₂ -] may be the same or different.

The group represented by Y ¹ [-Si(R) _n L _3-n ] _g in formula (1) is preferably groups (3-1A-1) to (3-1A-7). When g=1, Y ¹ [-Si(R) _n L _3-n ] _g is a group (3-1A-1). Groups (3-1A-2) to (3-1A-7) are specific examples of group (3-1A).
-Si(R) _n L _3-n ...(3-1A-1)
-N[-Q ^b2 -Si(R) _n L _3-n ] ₂ ...(3-1A-2)
-Si(R ^g ) [-Q ^b3 -Si(R) _n L _3-n ] ₂ ...(3-1A-3)
-C[-(O) _u4 -Q ^b4 -Si(R) _n L _3-n ] _3-w1 (-R ³¹ ) _w1 ...(3-1A-4)
-Si[-Q ^b5 -Si(R) _n L _3-n ] ₃ ...(3-1A-5)
-Z ^a [-Q ^b6 -Si(R) _n L _3-n ] _w2 ...(3-1A-6)
-Z ^c [-(O-Q ^b4 ) _u4 -Si(R) _n L _3-n ] _w3 (-OH) _w4 ...(3-1A-7)
Note that in formulas (3-1A-1) to (3-1A-7), the definitions of R, L, and n are as described above.

Q ^b2 is an alkylene group or a group having a divalent organopolysiloxane residue, an ether oxygen atom, or -NH- between carbon atoms of an alkylene group having 2 or more carbon atoms.
The number of carbon atoms in the alkylene group represented by Q ^b2 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
The number of carbon atoms in the group having a divalent organopolysiloxane residue, an ether oxygen atom, or -NH- between the carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q ^b2 is 2 to 20. is preferable, 2 to 10 is more preferable, and 2 to 6 is even more preferable.

As Q ^b2 , -CH ₂ CH ₂ CH ₂ -, -CH ₂ CH ₂ OCH ₂ CH ₂ CH ₂ - are preferable from the viewpoint of easy production of the compound (provided that the right side is bonded to Si).

The two [-Q ^b2 -Si(R) _n L _3-n ] may be the same or different.

Specific examples of the group (3-1A-2) include the following groups. In the following formula, * represents the bonding position with Z. Further, in the formula, α in (CH ₂ ) _α bonded to the reactive silyl group is an integer representing the number of methylene groups, preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, It may be from 2 to 10, or from 2 to 6. Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10. A plurality of α's contained in the same compound may be the same or different, but are preferably the same. For example, all of the plurality of αs contained in the same compound are 2, 3, 8, 9, and 11. The same applies below.

In the group (3-1A-3), R ^g is a hydrogen atom, a hydroxyl group, or an alkyl group.
From the viewpoint of easy production of the compound, R ^g is preferably a hydrogen atom or an alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably a methyl group.

Q ^b3 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of an alkylene group having 2 or more carbon atoms.
The number of carbon atoms in the alkylene group represented by Q ^b3 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
The carbon number of the group having an ether oxygen atom or a divalent organopolysiloxane residue between the carbon atoms of the alkylene group having 2 or more carbon atoms, represented by Q ^b3 , is preferably 2 to 20, and 2 to 20. 10 is more preferable, and 2 to 6 is even more preferable.
Q ^b3 is preferably -CH ₂ CH ₂ -, -CH ₂ CH ₂ CH ₂ -, or -CH ₂ CH 2 CH ₂ CH ₂ CH 2 CH ₂ _{CH 2} _CH ₂ _- from the viewpoint of easy production of the compound.

The two [-Q ^b3 -Si(R) _n L _3-n ] may be the same or different.

Specific examples of the group (3-1A-3) include the following groups. In the following formula, * represents the bonding position with Z.

In the group (3-1A-4), Q ^b4 is an alkylene group, and the alkylene group is -O-, -C(O)N(R ^d )- (the definition of R ^d is as described above) ), may or may not have a silphenylene skeleton group, a divalent organopolysiloxane residue, or a dialkylsilylene group.
In addition, when the alkylene group has -O- or a silphenylene skeleton group, it is preferable to have -O- or a silphenylene skeleton group between carbon atoms. In addition, when the alkylene group has -C(O)N(R ^d )-, a dialkylsilylene group, or a divalent organopolysiloxane residue, the terminal between carbon atoms or the side bonded to (O) _u4 preferably has these groups.
The number of carbon atoms in the alkylene group represented by Q ^b4 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the range may be from 1 to 10.

u4 is 0 or 1.
-(O) _u4 -Q ^b4 - includes -CH ₂ CH ₂ -, -CH 2 CH 2 CH ₂ -, -CH ₂ _OCH ₂ CH ₂ _CH ₂ -, -CH ₂ from the viewpoint of easy production of the compound. OCH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -, -OCH ₂ CH ₂ CH ₂ -, -OSi(CH ₃ ) ₂ CH ₂ CH ₂ CH ₂ -, -OSi(CH ₃ ) ₂ OSi(CH ₃ ) ₂ CH ₂ CH ₂ CH ₂ -- and --CH ₂ CH ₂ CH ₂ Si(CH ₃ ) ₂ PhSi(CH ₃ ) ₂ CH ₂ CH ₂ -- are preferred (however, the right side is bonded to Si).

w1 is 0 or 1, and 0 is more preferable.
If there are two or more [-(O) _u4 -Q ^b4 -Si(R) _n L _3-n ], two or more [-(O) _u4 -Q ^b4 -Si(R) _n L _{3- n} ] may be the same or different.
When there are two or more R ³¹ s, two or more (-R ³¹ )s may be the same or different.

Specific examples of the group (3-1A-4) include the following groups. In the following formula, * represents the bonding position with Z.

In the group (3-1A-5), Q ^b5 is an alkylene group, or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of an alkylene group having 2 or more carbon atoms. It is.
The number of carbon atoms in the alkylene group represented by Q ^b5 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
The number of carbon atoms in the group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q ^b5 is preferably 2 to 20, and 2 to 20. 10 is more preferable, and 2 to 6 is even more preferable.
From the viewpoint of easy production of the compound, Q ^b5 is preferably -CH ₂ CH ₂ CH ₂ - and -CH ₂ CH ₂ OCH ₂ CH ₂ CH ₂ - (provided that the right side is Si(R) _n L _3- bond to _n ).

The three [-Q ^b5 -Si(R) _n L _3-n ] may be the same or different.

Specific examples of the group (3-1A-5) include the following groups. In the following formula, * represents the bonding position with Z.

In the group (3-1A-6), Z ^a is a (w2+1)-valent organopolysiloxane residue, or a (w2+1)-valent organopolysiloxane residue between the organopolysiloxane residues. It is a group having an alkylene group.
w2 is an integer from 2 to 7.
Examples of (w2+1)-valent organopolysiloxane residues and (w2+1)-valent groups having an alkylene group between organopolysiloxane residues include the following groups: . However, R ^a in the following formula is as described above.

Q ^b6 is an alkylene group or a group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms of an alkylene group having 2 or more carbon atoms.
The number of carbon atoms in the alkylene group represented by Q ^b6 is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. . Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10.
The carbon number of the group having an ether oxygen atom or a divalent organopolysiloxane residue between the carbon atoms of the alkylene group having 2 or more carbon atoms represented by Q ^b6 is preferably 2 to 20, and 2 to 20. 10 is more preferable, and 2 to 6 is even more preferable.
As Q ^b6 , -CH ₂ CH ₂ - and -CH ₂ CH ₂ CH ₂ - are preferable from the viewpoint of easy production of the compound.
w2 [-Q ^b6 -Si(R) _n3 L _3-n ] may be the same or different.

Specific examples of the group (3-1A-6) include the following groups. In the following formula, * represents the bonding position with Z.

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

Z ^c may consist of a hydrocarbon chain, may have an ether oxygen atom between carbon atoms of the hydrocarbon chain, and is preferably composed of a hydrocarbon chain.
The valence of Z ^c is preferably 5 to 20, more preferably 5 to 10, even more preferably 5 to 8, particularly preferably 5 to 6.
The number of carbon atoms in Z ^c is preferably 3 to 50, more preferably 4 to 40, even more preferably 5 to 30.
w3 is preferably from 4 to 20, more preferably from 4 to 16, even more preferably from 4 to 8, particularly preferably from 4 to 5.
w4 is preferably 0 to 10, more preferably 0 to 8, even more preferably 0 to 6, particularly preferably 0 to 3, and most preferably 0 to 1.
Two or more [-(O-Q ^b4 ) _u4 -Si(R ¹ ) _n L _3-n ] may be the same or different.

Specific examples of the group (3-1A-7) include the following groups. In the following formula, * represents the bonding position with Z.

Y ¹ in formula (1) may be groups (g2-1) to (g2-6). In the formula, * represents a bonding site with Z.

*-C(R ^e2 ) _3-e2 (-Q ²² -) _e2 ...(g2-2)
*-N(-Q ²³ -) ₂ ...(g2-3)
*-Z ¹ (-Q ²⁴ -) _h2 ...(g2-4)
*-Si(R ^e3 ) _3-i2 (-Q ²⁵ -) _i2 ...(g2-5)
*-CH(-Q ²² -)-Si(R ^e3 ) _3-i3 (-Q ²⁵ -) _i3 ...(g2-6)

However, in formulas (g2-1) to (g2-6), the * side is connected to Z, and the Q ²² , Q ²³ , Q ²⁴ , or Q ²⁵ side is connected to [-Si(R) _n L _3-n ]. Connecting.
Q ¹¹ is a single bond, -O-, an alkylene group, or a bond between carbon atoms of an alkylene group having 2 or more carbon atoms -C(O)NR ⁶ -, -C(O)-, -NR ⁶ -, or It is a group having O-.
Q ²² is an alkylene group, a group having -C(O)NR ⁶ -, -C(O)-, -NR ⁶ - or O- between carbon atoms of an alkylene group having 2 or more carbon atoms, an alkylene group A group having -C(O)NR ⁶ -, -C(O)-, -NR ⁶ - or O- at the end not connected to Si, or between carbon atoms of an alkylene group having 2 or more carbon atoms -C(O)NR ⁶ -, -C(O)-, -NR ⁶ - or O- at the end not connected to Si and -C(O)NR ⁶ -, -C(O) It is a group having -, -NR ⁶ - or O-, and when two or more Q ^22s exist, two or more Q ^22s may be the same or different.
Q ²³ is an alkylene group or a group having -C(O)NR ⁶ -, -C(O)-, -NR ⁶ - or O- between carbon atoms of an alkylene group having 2 or more carbon atoms; , two ^Q23s may be the same or different.
Q ²⁴ is Q ²² when the atom in Z ¹ to which Q 24 is bonded is a carbon atom, and is Q ²³ when the atom ⁱⁿ Z ¹ to which Q ²⁴ is bonded is a nitrogen atom, and two or more Q ²⁴ exist. In this case, two or more ^Q24 's may be the same or different.
Q ²⁵ is an alkylene group or a group having -C(O)NR ⁶ -, -C(O)-, -NR ⁶ - or O- between carbon atoms of an alkylene group having 2 or more carbon atoms; , Q ²⁵ exists, two or more Q ²⁵ may be the same or different.
Z ¹ is a group having a (h2+1)-valent ring structure in which Z has a carbon atom or nitrogen atom to which Z is directly bonded, and Q ²⁴ has a carbon atom or nitrogen atom to which Q 24 is directly bonded.
R ^e1 is a hydrogen atom or an alkyl group, and when two or more R ^e1s exist, two or more R ^e1s may be the same or different.
R ^e2 is a hydrogen atom, a hydroxyl group, an alkyl group, or an acyloxy group.
R ^e3 is an alkyl group. R ⁶ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.

d2 is an integer from 0 to 3, preferably 1 or 2.
d4 is an integer from 0 to 3, preferably 2 or 3.
d2+d4 is an integer from 2 to 5, preferably 4 or 5.
e2 is 2 or 3.
h2 is an integer of 2 or more, preferably 2 or 3.
i2 is 2 or 3.
i3 is 2 or 3.

The number of carbon atoms in the alkylene groups of Q ¹¹ , Q ²² , Q ²³ , Q ²⁴ , and Q ²⁵ is preferably 1 to 30 from the viewpoint of excellent ease of manufacturing the compound and from the viewpoint of further improving the abrasion resistance of the surface treatment layer. It is preferably 1 to 20, more preferably 2 to 20, may be 2 to 10, or may be 2 to 6. Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4. However, when the alkylene group has a specific bond between carbon atoms, the lower limit of the number of carbon atoms is 2.

Examples of the ring structure in Z ¹ include the ring structures described above, and preferred forms are also the same. Note that since Z and Q ²⁴ are directly bonded to the ring structure of Z ¹ , for example, an alkylene group is not bonded to the ring structure and Z and Q ²⁴ are not bonded to the alkylene group.

The number of carbon atoms in the alkyl group of R ^e1 , R ^e2 or R ^e3 is preferably from 1 to 6, more preferably from 1 to 3, even more preferably from 1 to 2, from the viewpoint of excellent ease of manufacturing the compound.
The number of carbon atoms in the alkyl group portion of the acyloxy group of R ^e2 is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of excellent ease of manufacturing the compound.
h2 is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3, from the viewpoint of excellent ease of manufacturing the compound and further excellent wear resistance of the surface treatment layer.

Y ¹ in formula (1) may be groups (g2-7) to (g2-13). In the formula, * indicates a bonding site with Z.

*-C(R ^e2 ) _3-e2 (-Q ²² -G ¹ ) _e2 ...(g2-8)
*-N(-Q ²³ -G ¹ ) ₂ ...(g2-9)
*-Z ¹ (-Q ²⁴ -G ¹ ) _h2 ...(g2-10)
*-Si(R ^e3 ) _3-i2 (-Q ²⁵ -G ¹ ) _i2 ...(g2-11)
*-G ¹ ...(g2-12)
*-CH(-Q ²² -G ¹ )-Si(R ^e3 ) _3-i3 (-Q ²⁵ -G ¹ ) _i3 ...(g2-13)

However, in formulas (g2-7) to (g2-13), the * side is connected to Z, and the G ¹ side is connected to [-Si(R) _n L _3-n ]. G ¹ is a group (g3), and two or more G ^1s in Y ¹ may be the same or different. The symbols other than G ¹ are the same as those in equations (g2-1) to (g2-6).
-Si(R ⁸ ) _3-k3 (-Q ³ -) _k3 ...(g3)
However, in formula (g3), the Si side is connected to Q ²² , Q ²³ , Q ²⁴ , and Q ²⁵ , and the Q ³ side is connected to [-Si(R) _n L _3-n ]. R ⁸ is an alkyl group. Q ³ is an alkylene group, a group having -C(O)NR ⁶ -, -C(O)-, -NR ⁶ - or -O- between carbon atoms of an alkylene group having 2 or more carbon atoms, or (OSi(R ⁹ ) ₂ ) _p -O-, and two or more Q ³ may be the same or different. k3 is 2 or 3. R ⁶ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. R ⁹ is an alkyl group, a phenyl group, or an alkoxy group, and two R ^9s may be the same or different. p is an integer from 0 to 5, and when p is 2 or more, two or more (OSi(R ⁹ ) ₂ ) may be the same or different.

The number of carbon atoms in the alkylene group of Q ³ is preferably 1 to 30, more preferably 1 to 20, more preferably 2 to 20, from the viewpoint of excellent ease of manufacturing the compound and from the viewpoint of further excellent wear resistance of the surface treatment layer. is more preferable, and may be from 2 to 10, or from 2 to 6. Examples include 2, 3, 8, 9, and 11. Further, the number of carbon atoms may be 1 to 10, 1 to 6, or 1 to 4. However, when the alkylene group has a specific bond between carbon atoms, the lower limit of the number of carbon atoms is 2.
The number of carbon atoms in the alkyl group of R ⁸ is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of excellent ease of manufacturing the compound.
The number of carbon atoms in the alkyl group of R ⁹ is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2 from the viewpoint of excellent ease of manufacturing the compound.
The number of carbon atoms in the alkoxy group of R ⁹ 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 the compound.
p is preferably 0 or 1.

Examples of the compound (1) include compounds of the following formula. The compound of the following formula is preferred from the viewpoints of easy industrial production, ease of handling, and superior abrasion resistance of the surface treatment layer. W in the compound of the following formula is the same as Ar-Z- in formula (1), and its preferred form is also the same.

Examples of the compound (1) in which Y ¹ is a group (g2-1) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-2) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-3) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-4) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-5) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-6) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-7) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-8) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-9) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-10) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-11) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-12) include compounds of the following formula.

Examples of the compound (1) in which Y ¹ is a group (g2-13) include compounds of the following formula.

Examples of the compounds of the present disclosure where g=1 in formula (1) include the following compounds.

Examples of the compounds of the present disclosure in which g is 2 or more in formula (1) and Y ¹ is a group (3-1A-4) include the following compounds.

Examples of the compounds of the present disclosure in which g is 2 or more in formula (1) and Y ¹ is a group (3-1A-6) include the following compounds.

The number average molecular weight (Mn) of the compound of the present disclosure is preferably 400 to 20,000, more preferably 500 to 18,000, and even more preferably 600 to 1,5000. When Mn is 400 or more, water repellency and abrasion resistance are excellent. When Mn is 20,000 or less, the viscosity can be easily controlled within an appropriate range, and solubility is improved, resulting in excellent handling properties during film formation.

[Method for producing compound]
The method for producing the compound of the present disclosure is not particularly limited. Examples of synthetic schemes for compounds of the present disclosure are shown below.

In one embodiment, the compound of the present disclosure is obtained by hydrosilylation of an intermediate represented by the following formula (1-1).
Ar-Z-Y ¹¹ (D) _g1 ...(1-1)
In formula (1-1),
Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms,
Z is a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. A divalent group containing at least one partial structure selected from
^Y11 is a single bond when g1 is 1, and is a (g1+1) valent linking group when g1 is 2 or more,
Each D is independently -Q ^L -CH=CH ₂ , where Q ^L is a single bond or a divalent linking group,
g1 is an integer of 1 or more.

Y ¹¹ (D) _g1 in formula (1-1) is -Y ¹ [-Si(R) _n L _3-n ] _g in formula (1) whose terminal is -CH ₂ -CH ₂ -Si(R) _n L _3-n group, the -CH ₂ -CH ₂ -Si(R) _n L _3-n group is replaced with -CH=CH ₂ .

An example of an intermediate of the compound of the present disclosure is shown below.

[Composition]
The composition of the present disclosure only needs to contain the compound of the present disclosure, and components other than the compound of the present disclosure are not particularly limited. Compositions of the present disclosure preferably include a compound of the present disclosure and a liquid medium. When the composition of the present disclosure includes a liquid medium, the composition of the present disclosure may be in a liquid state, and may be a solution or a dispersion.
The composition of the present disclosure only needs to contain the compound of the present disclosure, and may contain impurities such as by-products generated in the manufacturing process of the compound of the present disclosure.
The composition of the present disclosure may contain one type of compound of the present disclosure, or may contain two or more types of compounds of the present disclosure.

The content of the compound of the present disclosure is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and further preferably 0.1 to 10% by mass, based on the total amount of the composition of the present disclosure. preferable. In the case of the composition of the present disclosure used in the wet coating method, the content of the compound of the present disclosure may be 0.01 to 10% by mass, based on the total amount of the composition of the present disclosure, and 0. It may be 0.02 to 5% by weight, 0.03 to 3% by weight, or 0.05 to 2% by weight.

The liquid medium is preferably an organic solvent.

Examples of organic solvents include compounds consisting only of hydrogen atoms and carbon atoms, and compounds consisting only of hydrogen atoms, carbon atoms, and oxygen atoms. Specifically, examples include hydrocarbon-based organic solvents, ketone-based organic solvents, and ethers. Examples include organic solvents based on organic solvents, organic solvents based on esters, organic solvents based on glycol, and organic solvents based on alcohol.
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, Examples include p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.
Specific examples of ketone organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, and 3,5,5-trimethyl-2-cyclohexen-1-one. Examples include 3,5-trimethylcyclohexanone and isophorone.
Specific examples of ether organic solvents include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, and 1,4-dioxane.
Specific examples of ester 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, and ethyl ethylene glycol lactate. Monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, ethylene glycol Monoethyl ether acetate, ethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, cyclohexanol acetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether acetate, propylene glycol mono Butyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol diacetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,4-butanediol diacetate, 1,3-butylene glycol diacetate Examples include acetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.
Specific examples of glycol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, and 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, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, Propylene glycol monobutyl ether tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butylene glycol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, diethylene glycol monoethyl ether, dipropylene glycol n-propyl ether, Propylene glycol n-butyl ether, tripropylene glycol methyl ether, tripropylene glycol n-butyl 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, dipropylene glycol dimethyl ether pentane, triethylene glycol dimethyl ether, and polyethylene glycol dimethyl ether.
Specific examples of alcoholic organic solvents include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3 -Butanediol, 1,3-butanediol, 1,3-butylene glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4 -Methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isotridecanol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol , 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol.

Further, examples of the organic solvent include halogenated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds.
Specific examples of halogenated organic solvents include dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, 1,2,3-trichloropropane. can be mentioned.
Examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone.
Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.
Examples of the siloxane compound include hexamethyldisiloxane, octamethyltrisiloxane, and decamethyltetrasiloxane.

The content of the liquid medium is preferably 60 to 99.999% by mass, more preferably 85 to 99.99% by mass, and even more preferably 90 to 99.9% by mass, based on the total amount of the composition of the present disclosure. In the case of the composition of the present disclosure used in a wet coating method, the content of the liquid medium may be 90-99.99% by weight, 95-99% by weight, based on the total amount of the composition of the present disclosure. It may be .98% by mass, 97 to 99.97% by mass, or 98 to 99.95% by mass.
The composition of the present disclosure may contain only one type of liquid medium, or may contain two or more types.

The composition of the present disclosure may contain other components in addition to the compound of the present disclosure and the liquid medium, as long as the effects of the present disclosure are not impaired.
Examples of other components include known additives such as acid catalysts and basic catalysts that promote hydrolysis and condensation reactions of reactive silyl groups.

In addition, other components include a metal compound having a hydrolyzable group (hereinafter, a metal compound having a hydrolyzable group is also referred to as a "specific metal compound"). When the composition of the present disclosure contains a specific metal compound, the slipperiness and antifouling properties of the surface treatment layer can be further improved. Specific metal compounds include the following formulas (M1) to (M3).

M(X ^b1 ) _m1 (X ^b2 ) _m2 (X ^b3 ) _m3 ...(M1)
Si(X ^b4 )(X ^b5 ) ₃ ...(M2)
(X ^b6 ) ₃ Si-(Y ^b1 )-Si(X ^b7 ) ₃ ...(M3)

In formula (M1),
M represents a trivalent or tetravalent metal atom.
Each of X ^b1 independently represents a hydrolyzable group.
Each of X ^b2 independently represents a siloxane skeleton-containing group.
Each of X ^b3 independently represents a hydrocarbon chain-containing group.
m1 is an integer from 2 to 4,
m2 and m3 are each independently an integer of 0 to 2,
When M is a trivalent metal atom, m1+m2+m3 is 3, and when M is a tetravalent metal atom, m1+m2+m3 is 4.

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

In formula (M3),
X ^b6 and X ^b7 each independently represent a hydrolyzable group or a hydroxyl group.
Y ^b1 represents a divalent organic group.

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

In formula (M1), the hydrolyzable group represented by X ^b1 is the same as the hydrolyzable group represented by L in [-Si(R ¹ ) _n L _3-n ] in the above reactive silyl group. Examples include:

The siloxane skeleton-containing group represented by X ^b2 has a siloxane unit (-Si-O-) and may be linear or branched. The siloxane unit is preferably a dialkylsilyloxy group, such as a dimethylsilyloxy group or a diethylsilyloxy group. The number of repeating siloxane units in the siloxane skeleton-containing group is 1 or more, preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3.
The siloxane skeleton-containing group may include a divalent hydrocarbon group in a part of the siloxane skeleton. Specifically, some oxygen atoms in the siloxane skeleton may be replaced with divalent hydrocarbon groups. Examples of the divalent hydrocarbon group include alkylene groups such as a methylene group, an ethylene group, a propylene group, and a butylene group.
A hydrolyzable group, a hydrocarbon group (preferably an alkyl group), etc. may be bonded to the terminal silicon atom of the siloxane skeleton-containing group.
The number of elements in the siloxane skeleton-containing group is preferably 100 or less, more preferably 50 or less, and even more preferably 30 or less. The number of elements is preferably 10 or more.
The siloxane skeleton-containing group is preferably a group represented by ^* -(O-Si(CH ₃ ) ₂ ) _n CH ₃ , where n is an integer from 1 to 5, and * represents a bond with an adjacent atom. Represents a part.

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

It is preferable that m1 is 3 or 4.

As the compound represented by formula (M1), compounds represented by the following formulas (M1-1) to (M1-5) where M is Si are preferable, and the compound represented by formula (M1-1) is More preferred. As the compound represented by formula (M1-1), tetraethoxysilane, tetramethoxysilane, and triethoxymethylsilane are preferred.

Si(X ^b1 ) ₄ ...(M1-1)
CH ₃ -Si(X ^b1 ) ₃ ...(M1-2)
C ₂ H ₅ -Si(X ^b1 ) ₃ ...(M1-3)
n-C ₃ H ₇ -Si(X ^b1 ) ₃ ...(M1-4)
(CH ₃ ) ₂ CH-Si(X ^b1 ) ₃ ... (M1-5)

In formula (M2), the number of silicon atoms contained in the hydrolyzable silane oligomer residue represented by X ^b4 is preferably 3 or more, more preferably 5 or more, and even more preferably 7 or more. The number of silicon atoms is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less.
The hydrolyzable silane oligomer residue may have an alkoxy group bonded to a silicon atom. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, and methoxy group and ethoxy group are preferred. The hydrolyzable silane oligomer residue may have one or more types of these alkoxy groups, and preferably has one type.
Examples of the hydrolyzable silane oligomer residue include (C ₂ H ₅ O) ₃ Si-(OSi(OC ₂ H ₅ ) ₂ ) ₄ O- ^* and the like. Here, * represents a bonding site with an adjacent atom.

In formula (M2), the hydrolyzable group represented by X ^b5 is the same as the hydrolyzable group represented by L in [-Si(R ¹ ) _n L _3-n ] in the above reactive silyl group. Examples include a cyano group, a hydrogen atom, and an allyl group, with an alkoxy group or an isocyanato group being preferred. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms.
As X ^b5 , a hydrolyzable group is preferable.

Examples of the compound represented by formula (M2) include (H ₅ C ₂ O) ₃ -Si-(OSi(OC ₂ H ₅ ) ₂ ) ₄ OC ₂ H ₅ and the like.

The compound represented by formula (M3) is a compound having a reactive silyl group at both ends of a divalent organic group, that is, bissilane.
In formula (M3), the hydrolyzable groups represented by X ^b6 and X ^b7 include an alkoxy group, an acyloxy group, a ketoxime group, an alkenyloxy group, an amino group, an aminoxy group, an amide group, an isocyanato group, and a halogen atom. an alkoxy group and an isocyanato group are preferred. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group.
In formula (M3), X ^b6 and X ^b7 may be the same group or different groups. From the viewpoint of availability, it is preferable that X ^b6 and X ^b7 are the same group.

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

Examples of the compound represented by formula (M3) include (CH ₃ O) ₃ Si(CH ₂ ) ₂ Si(OCH ₃ ) ₃ , (C ₂ H ₅ O) ₃ Si(CH ₂ ) ₂ Si(OC ₂ H ₅ ) ₃ , (OCN) _3Si ( _CH2 ) _2Si ( _NCO ) ₃ , Cl3Si( _CH2 ) _2SiCl3 _, ( _CH3O ) _3Si ( _CH2 ) _6Si ( _OCH3 ) ₃ , ₍ _C2H5O ) _3Si ( _CH2 ) _6Si ( _OC2H5 ) ₃ _is mentioned.

The content of other components that may be included in the composition of the present disclosure is preferably 10% by mass or less, more preferably 1% by mass or less, based on the total amount of the composition of the present disclosure. When the composition of the present disclosure includes a specific metal compound, the content of the specific metal compound is preferably 0.01 to 30% by mass, more preferably 0.01 to 10% by mass based on the total amount of the composition of the present disclosure. , more preferably 0.05 to 5% by mass.

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

The composition of the present disclosure is useful for coating purposes and can be used as a coating liquid.

[Surface treatment agent]
In one aspect, the surface treatment agent of the present disclosure comprises a compound of the present disclosure. Furthermore, the surface treatment agent of the present disclosure may include the compound of the present disclosure and a liquid medium. The surface treating agent of the present disclosure may be a composition of the present disclosure. Preferred embodiments of the liquid medium contained in the surface treatment agent are the same as those of the liquid medium contained in the composition of the present disclosure.

Since the compound of the present disclosure has the above-mentioned structure, a surface treatment layer with excellent water repellency and abrasion resistance can be formed by using a surface treatment agent containing the compound of the present disclosure.

[Goods]
In one aspect, the article of the present disclosure includes a base material and a surface treatment layer surface treated with the surface treatment agent.

The surface treatment layer may be formed on a part of the surface of the base material, or may be formed on the entire surface of the base material. The surface treatment layer may be spread over the surface of the base material in the form of a film, or may be scattered in the form of dots.
In the surface treatment layer, the compound of the present disclosure is contained in a state in which hydrolysis of some or all of the reactive silyl groups has proceeded, and a dehydration condensation reaction of the silanol groups has proceeded.

The thickness of the surface treatment layer is preferably 1 to 100 nm, more preferably 1 to 50 nm. If the thickness of the surface treatment layer is 1 nm or more, the effect of the surface treatment is likely to be sufficiently obtained. If the thickness of the surface treatment layer is 100 nm or less, the utilization efficiency is high. The thickness of the surface treatment layer is determined by using an X-ray diffractometer for thin film analysis (product name "ATX-G", manufactured by RIGAKU) to obtain an interference pattern of reflected X-rays by the X-ray reflectance method. It can be calculated from the vibration period of

The type of base material is not particularly limited, and includes, for example, base materials that are required to have water repellency. As a base material, for example, a base material that may be used in contact with another article (e.g., a stylus) or a person's fingers; a base material that may be held by a person's fingers during operation; , a mounting table).
Examples of the base material include metal, resin, glass, sapphire, ceramic, stone, fiber, nonwoven fabric, paper, wood, natural leather, artificial leather, and composite materials thereof. The glass may be chemically strengthened.

Base materials include building materials, decorative building materials, interior goods, transportation equipment (e.g. automobiles), signboards, bulletin boards, drinking vessels, tableware, aquariums, ornamental equipment (e.g. frames, boxes), laboratory equipment, furniture, and textile products. , Packaging containers; Glass or resin used for art, sports, games, etc.; Used for the exterior parts (excluding display parts) of devices such as mobile phones (e.g. smartphones), personal digital assistants, game consoles, remote controls, etc. Examples include glass or resin. The shape of the base material may be plate-like or film-like.

As the base material, touch panel base materials, display base materials, and eyeglass lenses are suitable, and touch panel base materials are particularly suitable. As the material for the touch panel base material, glass or transparent resin is preferable.

The base material may be a base material that has been subjected to surface treatment such as corona discharge treatment, plasma treatment, plasma graft polymerization treatment, etc. on one surface or both surfaces. A surface-treated base material has better adhesion with the surface-treated layer, and the abrasion resistance of the surface-treated layer is further improved. Therefore, it is preferable to perform surface treatment on the surface of the base material that is in contact with the surface treatment layer. Furthermore, when the surface-treated base material is provided with a base layer, which will be described later, the adhesion with the base layer is better, and the wear resistance of the surface-treated layer is further improved. Therefore, when a base layer is provided, it is preferable to perform a surface treatment on the surface of the base material that is in contact with the base layer.

The surface treatment layer may be provided directly on the surface of the base material, or a base layer may be provided between the base material and the surface treatment layer. From the perspective of further improving the water repellency and abrasion resistance of the surface treatment layer, the article of the present disclosure includes a base material, a base layer disposed on the base material, and a surface treatment of the present disclosure disposed on the base layer. It is preferable to include a surface treatment layer whose surface is treated with an agent.

The base layer includes silicon and at least one selected from the group consisting of a group 1 element, a group 2 element, a group 4 element, a group 5 element, a group 13 element, and a group 15 element of the periodic table. A layer containing an oxide containing a specific element is preferable.

Group 1 elements of the periodic table (hereinafter also referred to as "Group 1 elements") mean lithium, sodium, potassium, rubidium, and cesium. As Group 1 elements, lithium, sodium, and potassium are used because they enable the surface treatment layer to be formed more uniformly on the underlayer without defects, and from the viewpoint of suppressing variations in the composition of the underlayer between samples. Preferably, sodium and potassium are more preferable. The underlayer may contain two or more types of Group 1 elements.

Group 2 elements of the periodic table (hereinafter also referred to as "Group 2 elements") mean beryllium, magnesium, calcium, strontium, and barium. As Group 2 elements, magnesium, calcium, and barium are used because they enable the surface treatment layer to be formed more uniformly on the underlayer without defects, and from the viewpoint of suppressing variations in the composition of the underlayer between samples. Preferably, magnesium and calcium are more preferable. The underlayer may contain two or more types of Group 2 elements.

Group 4 elements of the periodic table (hereinafter also referred to as "Group 4 elements") mean titanium, zirconium, and hafnium. As the Group 4 element, titanium and zirconium are preferable from the viewpoint of being able to form a surface treatment layer on the underlayer more uniformly without defects or from the viewpoint of suppressing variations in the composition of the underlayer between samples. Titanium is more preferred. The base layer may contain two or more types of Group 4 elements.

Group 5 elements of the periodic table (hereinafter also referred to as "Group 5 elements") mean vanadium, niobium, and tantalum. As the Group 5 element, vanadium is particularly preferable from the viewpoint of providing better wear resistance of the surface treatment layer. The underlayer may contain two or more types of Group 5 elements.

Group 13 elements of the periodic table (hereinafter also referred to as "Group 13 elements") mean boron, aluminum, gallium, and indium. As Group 13 elements, boron, aluminum, and gallium are selected from the viewpoint of forming a surface treatment layer on the underlayer more uniformly without defects, or from the viewpoint of suppressing variations in the composition of the underlayer between samples. Preferably, boron and aluminum are more preferable. The base layer may contain two or more types of Group 13 elements.

Group 15 elements of the periodic table (hereinafter also referred to as "Group 15 elements") mean nitrogen, phosphorus, arsenic, antimony, and bismuth. As Group 15 elements, phosphorus, antimony, and bismuth are used from the viewpoint of forming a surface treatment layer on the underlayer more uniformly without defects or from the viewpoint of suppressing variations in the composition of the underlayer between samples. Preferably, phosphorus and bismuth are more preferable. The base layer may contain two or more types of Group 15 elements.

As the specific elements contained in the underlayer, Group 1 elements, Group 2 elements, and Group 13 elements are preferable because the wear resistance of the surface treatment layer is better, and Group 1 elements and Group 2 elements are more preferable. , Group 1 elements are more preferred.
As the specific element, only one type of element may be included, or two or more types of elements may be included.

The oxide contained in the base layer may be a mixture of oxides of the above elements (silicon and specific elements) alone (for example, a mixture of silicon oxide and an oxide of a specific element), or a mixture of the above elements (silicon and specific elements). It may be a composite oxide containing two or more types, or a mixture of an oxide of the above element alone and a composite oxide.

The ratio of the total molar concentration of the specific element in the underlayer to the molar concentration of silicon in the underlayer (specific element/silicon) is 0.02 to 2.90 from the viewpoint of better wear resistance of the surface treatment layer. It is preferably 0.10 to 2.00, even more preferably 0.20 to 1.80.
The molar concentration (mol %) of each element in the underlayer can be measured, for example, by depth direction analysis using X-ray photoelectron spectroscopy (XPS) using ion sputtering.

The base layer may be a single layer or a multilayer. The base layer may have an uneven surface.
The thickness of the underlayer is preferably 1 to 100 nm, more preferably 1 to 50 nm, and even more preferably 2 to 20 nm. If the thickness of the base layer is equal to or greater than the above lower limit, the adhesion of the surface treatment layer to the base layer will be further improved, and the wear resistance of the surface treatment layer will be more excellent. If the thickness of the base layer is below the above upper limit, the base layer itself will have excellent wear resistance.
The thickness of the base layer is measured by observing a cross section of the base layer using a transmission electron microscope (TEM).

The base layer can be formed, for example, by a vapor deposition method using a vapor deposition material or a wet coating method.

The vapor deposition material used in the vapor deposition method preferably contains an oxide containing silicon and a specific element.
Specific examples of the form of the vapor deposition material include powder, molten body, sintered body, granulated body, and crushed body, and from the viewpoint of ease of handling, molten body, sintered body, and granulated body are preferable.
Here, the melt means a solid obtained by melting the powder of the vapor deposition material at a high temperature and then cooling and solidifying the powder. A sintered body means a solid obtained by firing a powder of a vapor deposition material, and if necessary, a molded body obtained by press-molding the powder may be used instead of a powder of a vapor deposition material. Good too. The granule refers to a solid material obtained by kneading a powder of a vapor deposition material and a liquid medium (for example, water, an organic solvent) to obtain particles, and then drying the particles.

The vapor deposition material can be manufactured, for example, by the following method.
・A method of obtaining a vapor deposition material powder by mixing silicon oxide powder and oxide powder of a specific element.
- A method of kneading the powder of the vapor deposition material and water to obtain particles, and then drying the particles to obtain granules of the vapor deposition material.
・Powders containing silicon (e.g. powder of silicon oxide, silica sand, silica gel) and powders containing specific elements (e.g. powder of oxides of specific elements, carbonates, sulfates, nitrates, oxalic acid) A method of obtaining a sintered body by drying a mixture of salt, hydroxide) and water, and then firing the dried mixture or a press-molded body of the dried mixture.
・Powders containing silicon (e.g. powder of silicon oxide, silica sand, silica gel) and powders containing specific elements (e.g. powder of oxides of specific elements, carbonates, sulfates, nitrates, oxalic acid) (salt, hydroxide) at high temperature, and then cooled and solidified to obtain a molten product.

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

Specific examples of evaporation methods include resistance heating, in which the evaporation material is melted and evaporated on a resistance heating boat made of high-melting-point metal, and irradiation of an electron beam onto the evaporation material to directly heat the evaporation material on the surface. An example is the electron gun method, which melts and evaporates. The method of evaporating the deposition material is that it can evaporate high-melting point substances because it can be heated locally, and that there is no risk of reaction with the container or contamination with impurities because the area that is not hit by the electron beam is at a low temperature. Gun law is preferred.
As a method for evaporating the evaporation materials, a plurality of boats may be used, or all the evaporation materials may be placed in a single boat. The vapor deposition method may be codeposition, alternate vapor deposition, or the like. Specifically, examples include mixing silica and a specific element source in the same boat, co-evaporating silica and a specific element source in separate boats, and alternately depositing silica and a specific element source in separate boats. can be mentioned. The conditions, order, etc. of vapor deposition are appropriately selected depending on the structure of the underlying layer.

In the wet coating method, it is preferable to form the base layer on the base material by a wet coating method using a coating liquid containing a compound containing silicon, a compound containing a specific element, and a liquid medium.

Specific examples of silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partially hydrolyzed condensates of alkoxysilanes.

Specific examples of compounds containing specific elements include oxides of specific elements, alkoxides of specific elements, carbonates of specific elements, sulfates of specific elements, nitrates of specific elements, oxalates of specific elements, and water of specific elements. Examples include oxides.

Examples of the liquid medium include those similar to the liquid medium contained in the composition of the present disclosure described above.

The content of the liquid medium is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, based on the total amount of the coating liquid used to form the base layer.

Specific examples of wet coating methods for forming the base layer include spin coating, wipe coating, spray coating, squeegee coating, dip coating, die coating, inkjet, flow coating, roll coating, Examples include the cast method, Langmuir-Blodgett method, and gravure coating method.

After wet coating the coating liquid, it is preferable to dry the coating film. The drying temperature of the coating film is preferably 20 to 200°C, more preferably 80 to 160°C.

The article of the present disclosure is preferably an optical member. Examples of optical components include medical devices such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game devices, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastrocameras. Examples include personal appliances, copying machines, PCs, displays (eg, liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and antireflection films. In particular, the article is preferably a display or a touch panel.

[Method for manufacturing articles]
A method for producing an article of the present disclosure is, for example, a method of surface-treating a base material using the surface treatment agent of the present disclosure to produce an article in which a surface-treated layer is formed on the base material. . Surface treatments include dry coating methods and wet coating methods.

Examples of dry coating methods include vacuum deposition, CVD, and sputtering. As the dry coating method, a vacuum evaporation method is preferable from the viewpoint of suppressing decomposition of the compound and the simplicity of the apparatus. At the time of vacuum deposition, a pellet-like substance obtained by impregnating a porous metal body such as iron or steel with the compound of the present disclosure may be used. A pellet-like material impregnated with the compound of the present disclosure may be used by impregnating a porous metal body such as iron or steel with a composition containing the compound of the present disclosure and a liquid medium, and drying the liquid medium.

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, and Langmuir-Blodgett methods. , gravure coating method.

In order to improve the abrasion resistance of the surface treatment layer, an operation may be performed to accelerate the reaction between the compound of the present disclosure and the base material, if necessary. Such operations include heating, humidification, light irradiation, and the like.
For example, by heating a base material on which a surface treatment layer is formed in a moist atmosphere, a hydrolysis reaction of hydrolyzable groups, a reaction between hydroxyl groups, etc. on the surface of the base material and silanol groups, and a condensation reaction of silanol groups. can promote reactions such as the formation of siloxane bonds.
After the surface treatment, compounds in the surface treatment layer that are not chemically bonded to other compounds or the base material may be removed as necessary. Examples of the removal method include a method of pouring a solvent onto the surface treatment layer, a method of wiping with a cloth impregnated with a solvent, and the like.

Next, embodiments of the present disclosure will be specifically described using Examples, but the embodiments of the present disclosure are not limited to these Examples.

[Synthesis Example 1: Synthesis of compound (1A)]
Tetrahydrofuran (THF. 100 g), copper chloride (0.3 g), and benzylmagnesium chloride (100 mL, approximately 16% THF solution) were added to 18-bromo-1-octadecene (30 g), and the mixture was heated at room temperature (approximately 25°C) for 24 hours. Stir for hours. After the reaction was completed, the solvent was distilled off under reduced pressure and flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane) was performed to obtain 22 g of compound (1A).

¹ H NMR (500 MHz, Chloroform-d) δ 7.34 - 6.98 (m, 5H), 5.80 (tt, J = 13.4, 6.1 Hz, 1H), 5.05 (dddt, J= 78.0, 13.3, 2.1, 1.0 Hz, 2H), 2.58 (tt, J = 7.0, 1.1 Hz, 2H), 2.21 - 1.89 (m, 2H), 1.71 - 1.08 (m, 30H).

[Synthesis Example 2: Synthesis of compound (1B)]
After adding 1,3-bistrifluoromethylbenzene (10 g) to the above compound (1A) (3.0 g) and stirring, platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex Toluene solution (platinum content: 3%, 0.1 g), aniline (0.1 g), and trimethoxysilane (1.5 g) were added, and after stirring at 40°C for 24 hours, the solvent was distilled off under reduced pressure. Thus, 4.0 g of the following compound (1B) was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 7.35 - 7.07 (m, 5H), 3.58 (s, 9H), 2.58 (tt, J = 7.0, 1.0 Hz, 2H), 1.75 - 1.11 (m, 34H) , 0.62 (t, J = 7.0 Hz, 2H).

[Synthesis Example 3: Synthesis of compound (2A)]
THF (20 g) and lithium aluminum hydride (1 g) were added to 4-(2-phenylethyl)benzoic acid (5.0 g), and the mixture was stirred at 20° C. for 24 hours. After the reaction was completed, sodium sulfate decahydrate and dichloromethane were added, filtered, and the solvent was distilled off. By performing flash column chromatography using silica gel (developing solvent: methanol/dichloromethane), 4.2 g of compound (2A) was obtained.

^1H NMR (500 MHz, Chloroform-d) δ 7.39 - 6.60 (m, 9H), 4.65 (dt, J = 6.4, 1.0 Hz, 2H), 3.05 - 2.65 (m, 4H).

[Synthesis Example 4: Synthesis of compound (2B)]
Diethyl ether (20 g) and phosphorus tribromide (8.0 g) were added to the above compound (2A) (4.2 g), and the mixture was stirred at room temperature (about 25° C.) for 1 hour. After the reaction was completed, ethyl acetate and water were added for extraction, and the solvent was distilled off. By performing flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane), 3.6 g of compound (2B) was obtained.

^1H NMR (500 MHz, Chloroform-d) δ 7.49 - 6.54 (m, 9H), 4.55 (d, J = 1.2 Hz, 2H), 3.03 - 2.63 (m, 4H).

[Synthesis Example 5: Synthesis of compound (2C)]
To the above compound (2B) (3.6 g) were added THF (20 g), copper chloride (0.3 g), and 10-undecen-1-ylmagnesium bromide (30 mL, 0.5 M in THF solution), and at room temperature (approx. The mixture was stirred at 25° C. for 24 hours. After extraction by adding hydrochloric acid and dichloromethane and distilling off the solvent, 3.8 g of compound (2C) was obtained by performing flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane).

¹ H NMR (500 MHz, Chloroform-d) δ 7.39 - 6.94 (m, 7H), 6.49 (dt, J = 7.6, 1.0 Hz, 2H), 5.80 (tt, J= 13.4, 6.1 Hz, 1H), 5.05 (dddt, J = 78.0, 13.3, 2.1, 0.9 Hz, 2H), 2.96 - 2.49 (m, 6H), 2.12 - 1.85 (m, 2H), 1.78 - 1.06 (m, 16H).

[Synthesis Example 6: Synthesis of compound (2D)]
After adding 1,3-bistrifluoromethylbenzene (10 g) to the above compound (2C) (3.0 g) and stirring, platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex Toluene solution (platinum content: 3%, 0.1 g), aniline (0.1 g), and trimethoxysilane (1.5 g) were added, and after stirring at 40°C for 24 hours, the solvent was distilled off under reduced pressure. Thus, 3.7 g of the following compound (2D) was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 7.39 - 6.95 (m, 7H), 6.49 (dt, J = 7.5, 1.0 Hz, 2H), 3.58 (s, 9H), 2.96 - 2.54 (m, 6H) , 1.76 - 1.13 (m, 20H), 0.62 (t, J = 7.0Hz, 2H).

[Synthesis Example 7: Synthesis of compound (3A)]
Diethyl ether (100 g) and phosphorus tribromide (30 g) were added to (E)-cinnamyl alcohol (13 g), and the mixture was stirred at room temperature (about 25° C.) for 1 hour. After the reaction was completed, ethyl acetate and water were added for extraction, and the solvent was distilled off. By performing flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane), 12 g of compound (3A) was obtained.

^1H NMR (500 MHz, Chloroform-d) δ 7.43 - 7.11 (m, 5H), 6.72 - 6.18 (m, 2H), 4.09(dd, J = 6.2, 1.0 Hz, 2H).

[Synthesis Example 8: Synthesis of compound (3B)]
THF (50 g), copper chloride (0.3 g), and 10-undecen-1-ylmagnesium bromide (100 mL, 0.5 M in THF solution) were added to the above compound (3A) (10 g), and room temperature (approximately 25°C) was added. ) for 24 hours. After the reaction was completed, hydrochloric acid and dichloromethane were added for extraction, and the solvent was distilled off, followed by flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane) to obtain 5.3 g of compound (3B). Ta.

¹ H NMR (500 MHz, Chloroform-d) δ 7.42 - 7.13 (m, 5H), 6.44 - 5.69 (m, 3H), 5.05(dddt, J = 78.2, 13.5, 2.3, 1.0 Hz, 2H), 2.37 ( tdd, J = 7.1, 6.1, 1.0 Hz, 2H), 2.20 - 1.89 (m, 2H), 1.59 - 1.07 (m, 16H).

[Synthesis Example 9: Synthesis of compound (3C)]
After adding 1,3-bistrifluoromethylbenzene (10 g) to the above compound (3B) (3.0 g) and stirring, platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex Toluene solution (platinum content: 3%, 0.1 g), aniline (0.1 g), and trimethoxysilane (1.5 g) were added, and after stirring at 40°C for 24 hours, the solvent was distilled off under reduced pressure. Thus, 4.1 g of the following compound (3C) was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 7.49 - 7.11 (m, 5H), 6.47 - 6.16 (m, 1H), 5.96 (dt, J = 15.2, 6.1 Hz, 1H), 3.58 (s, 9H) , 2.37 (tdd, J = 7.1, 6.2, 1.0 Hz, 2H), 1.61 - 1.06 (m, 20H), 0.62 (t, J = 7.0 Hz, 2H).

[Synthesis Example 10: Synthesis of compound (4A)]
4-phenyl-1-butene (15 g), allyl bromide (70 g), dichloromethane (200 g), and second generation HOVEYDA-GRUBBS catalyst (1.4 g) were added and stirred at room temperature (about 25° C.) for 6 hours. Ta. After distilling off the solvent under reduced pressure, 12 g of compound (4A) was obtained by performing flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane).

^1H NMR (500 MHz, Chloroform-d) δ 7.41 - 6.84 (m, 5H), 5.96 - 5.41 (m, 2H), 4.10 - 3.54 (m, 2H), 2.78 - 2.10 (m, 4H).

[Synthesis Example 11: Synthesis of compound (4B)]
To the above compound (4A) (11 g) were added THF (50 g), copper chloride (0.3 g), and 10-undecen-1-ylmagnesium bromide (100 mL, 0.5 M, in THF solution), and at room temperature (approximately 25°C). ) for 24 hours. After the reaction was completed, hydrochloric acid and dichloromethane were added for extraction, and the solvent was distilled off, followed by flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane) to obtain 6.7 g of compound (4B). Ta.

¹ H NMR (500 MHz, Chloroform-d) δ 7.41 - 6.93 (m, 5H), 5.80 (tt, J = 13.3, 6.1 Hz, 1H), 5.60 - 5.34 (m, 2H), 5.05 (dddt, J = 78.0, 13.4, 2.1, 1.0 Hz, 2H), 2.78 - 1.78 (m, 8H), 1.59 - 1.05 (m, 16H).

[Synthesis Example 12: Synthesis of compound (4C)]
After adding 1,3-bistrifluoromethylbenzene (10 g) to the above compound (4B) (3.0 g) and stirring, platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex Toluene solution (platinum content: 3%, 0.1 g), aniline (0.1 g), and trimethoxysilane (1.5 g) were added, and after stirring at 40°C for 24 hours, the solvent was distilled off under reduced pressure. Thus, 4.0 g of the following compound (4C) was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 7.33 - 6.97 (m, 5H), 5.61 - 5.24 (m, 2H), 3.58 (s, 9H), 2.63 (tt, J = 7.1, 1.0 Hz, 2H) , 2.32 - 1.82 (m, 4H), 1.62 - 1.06 (m, 20H), 0.62 (t, J= 7.0 Hz, 2H).

[Synthesis Example 13: Synthesis of compound (5A)]
After adding 1,3-bistrifluoromethylbenzene (10 g) to the above compound (1A) (3.4 g) and stirring, platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (Platinum content: 3%, 0.1 g), aniline (0.1 g), and 2,4,6,8-tetramethylcyclotetrasiloxane (3.0 g) were added, and the mixture was stirred at 40°C for 24 hours. After that, the solvent was distilled off under reduced pressure. Subsequently, 1,3-bistrifluoromethylbenzene (10 g) was added again, and after stirring, a toluene solution of platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content 3 %, 0.1g), aniline (0.1g), and vinyltrimethoxysilane (3.0g), and after stirring at 40°C for 24 hours, the following compound (5A) was obtained by distilling off the solvent under reduced pressure. 5.9g was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 7.40 - 7.00 (m, 5H), 3.58 (d, J = 2.4 Hz, 27H), 2.58 (tt, J = 7.0, 1.0 Hz, 2H), 1.75 - 1.09 (m, 34H), 0.97 - 0.50 (m, 14H), -0.08 (d, J= 4.3 Hz, 12H).

[Synthesis Example 14: Synthesis of compound (6A)]
After dissolving 18-bromo-1-octadecene (30 g) in dimethylformamide (200 g), sodium acetate (10 g) was added and the mixture was stirred at 80° C. for 24 hours. After extraction by adding diethyl ether and water and distilling off the solvent, methanol (400 g) and 200 g of 1M NaOH aqueous solution were added and stirred at 60° C. for 24 hours. After extraction by adding diethyl ether and water and distilling off the solvent, 22 g of compound (6A) was obtained by performing flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane).

¹ H NMR (500 MHz, Chloroform-d) δ 5.80 (tt, J = 13.4, 6.1 Hz, 1H), 5.05 (dddt, J = 78.0, 13.3, 2.1, 1.0 Hz, 2H), 3.55 (q, J = 7.0 Hz, 2H), 2.26 - 1.89 (m, 2H), 1.70 - 1.10 (m, 28H).

[Synthesis Example 15: Synthesis of compound (6B)]
THF (20 g) and sodium hydride (0.7 g) were added to the above compound (6A) (5.5 g), and the mixture was stirred at 20 degrees for 10 minutes. Subsequently, 4-fluorophenylsulfur pentafluoride (4.6 g) was added and stirred at 20°C for 24 hours. After completion of the reaction, extraction was performed by adding hydrochloric acid and dichloromethane, the solvent was distilled off, and then flash column chromatography using silica gel (developing solvent: ethyl acetate/hexane) was performed to convert compound (6B) into 6. I got 8g.

¹ H NMR (500 MHz, Chloroform-d) δ 8.17 - 7.56 (m, 2H), 7.43 - 6.83 (m, 2H), 5.80 (tt, J = 13.3, 6.1 Hz, 1H), 5.05 (dddt, J = 78.1, 13.4, 2.1, 1.0 Hz, 2H), 3.99 (t, J = 7.1 Hz, 2H), 2.19 - 1.93 (m, 2H), 1.86 - 1.06 (m, 28H).

[Synthesis Example 16: Synthesis of compound (6C)]
After adding 1,3-bistrifluoromethylbenzene (10 g) to the above compound (6B) (3.0 g) and stirring, platinum/1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex Toluene solution (platinum content: 3%, 0.1 g), aniline (0.1 g), and trimethoxysilane (1.5 g) were added, and after stirring at 40°C for 24 hours, the solvent was distilled off under reduced pressure. Thus, 3.6 g of the following compound (6C) was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 8.18 - 7.60 (m, 2H), 7.36 - 6.72 (m, 2H), 3.99 (t, J= 7.1 Hz, 2H), 3.58 (s, 9H), 1.95 - 0.96 (m, 32H), 0.62 (t, J = 7.0 Hz, 2H).

[Synthesis Example 17: Synthesis of compound (7A)]
1,3-bistrifluoromethylbenzene (10 g) was added to 12-phenyldodecene (4.8 g, manufactured by Gelest, product number ENEP3620), and after stirring, platinum/1,3-divinyl-1,1,3 , 3-Tetramethyldisiloxane complex toluene solution (platinum content 3%, 0.1 g), aniline (0.1 g), and trimethoxysilane (3.0 g) were added, and after stirring at 40 ° C. for 24 hours. By distilling off the solvent under reduced pressure, 6.9 g of the following compound (7A) was obtained.

¹ H NMR (500 MHz, Chloroform-d) δ 7.46 - 6.99 (m, 5H), 3.58 (s, 9H), 2.58 (tt, J = 7.0, 1.0 Hz, 2H), 1.74 - 1.11 (m, 20H) , 0.62 (t, J = 7.0 Hz, 2H).

[Manufacture and evaluation of articles]
The substrates were surface treated using compounds (1B), (2D), (3C), (4C), (5A), (6C) and (7A) to obtain articles of Examples 1 to 7, respectively. As a surface treatment method, the following dry coating method was used for each example. Chemically strengthened glass was used as the base material. The obtained article was evaluated by the following method. The results are shown in Table 1.

(Dry coating method)
The dry coating was performed using a vacuum evaporation device (VTR350M, manufactured by ULVAC) (vacuum evaporation method). 0.5 g of a 20% ethyl acetate solution of each compound was filled into a molybdenum boat in a vacuum evaporation apparatus, and the inside of the vacuum evaporation apparatus was evacuated to 1×10 ⁻³ Pa or less. The boat containing the compound is heated at a temperature increase rate of 10°C/min or less, and when the deposition rate exceeds 1 nm/sec using a crystal oscillation film thickness meter, the shutter is opened to form a film on the surface of the substrate. started. When the film thickness reached approximately 50 nm, the shutter was closed to complete the film formation on the surface of the substrate. The substrate on which the compound was deposited was heat-treated at 150° C. for 30 minutes to obtain an article having a surface layer on the surface of the substrate.

(Evaluation method)
<Water repellency>
The contact angle of about 2 μL of distilled water placed on the surface of the surface treatment layer was measured using a contact angle measuring device (DM-500, manufactured by Kyowa Interface Science Co., Ltd.). Measurements were made at five different locations on the surface of the surface treatment layer, and the average value was calculated. The 2θ method was used to calculate the contact angle. The evaluation criteria are as follows. A and B are at levels that pose no practical problems.
A: It is 100 degrees or more.
B: 90 degrees or more and less than 100 degrees.
C: Less than 90 degrees.

<Lipophilicity>
The contact angle of about 2 μL of oleic acid placed on the surface of the surface treatment layer was measured using a contact angle measuring device (DM-500, manufactured by Kyowa Interface Science Co., Ltd.). Measurements were made at five different locations on the surface of the surface layer, and the average value was calculated. The 2θ method was used to calculate the contact angle. The evaluation criteria are as follows. A and B are at levels that pose no practical problems.
A: Less than 10 degrees.
B: 10 degrees or more and less than 15 degrees.
C: 15 degrees or more.

<Low fingerprint visibility>
Sebum was applied to the glass substrate prepared above under a load of 1 kg, and its visibility was visually evaluated in the following four stages. The evaluation criteria are as follows.
4: Fingerprints are almost invisible 3: Fingerprints are slightly visible 2: Fingerprints are thin but clearly visible 1: Fingerprints are clearly visible

<Abrasion resistance (steel wool)>
Regarding the surface treatment layer of the article, steel wool Bonstar (#0000) was tested at a pressure of 98.07 kPa using a reciprocating traverse tester (manufactured by KNT) in accordance with JIS L0849:2013 (ISO 105-X12:2001). After reciprocating 10,000 times at a speed of 320 cm/min, the water contact angle was measured by the method described above. The smaller the drop in water repellency (water contact angle) after wear, the smaller the drop in performance due to friction, and the better the wear resistance. The evaluation criteria are as follows. A and B are at levels that pose no practical problems.
A: After 10,000 reciprocations, the water contact angle decreases by 5 degrees or less.
B: After 10,000 reciprocations, the water contact angle decreases from more than 5 degrees to 10 degrees or less.
C: The water contact angle decreases by more than 10 degrees after 10,000 reciprocations.

Examples 1 to 6 are examples, and example 7 is a comparative example. As shown in Table 1, the surface treatment layers prepared in Examples 1 to 6 have excellent abrasion resistance, but the surface treatment layer prepared in Example 7 has poor abrasion resistance. Furthermore, the surface treated layers prepared in Examples 1 to 6 are also excellent in water repellency, lipophilicity, and low fingerprint visibility.
The surface treatment layers made in Examples 2 and 3 have particularly good lipophilicity and low fingerprint visibility. The reason for this is not clear, but it is due to the fact that Compound 2 further has an aromatic ring near the terminal aromatic ring group, and Compound 3 has a double bond near the terminal aromatic ring group. It is assumed that.
The surface treatment layer produced in Example 5 has particularly good abrasion resistance. Although the reason for this is not clear, it is presumed that the wear resistance is improved due to the presence of a plurality of reactive silyl groups in the molecule.
The surface treated layer produced in Example 6 has particularly excellent water repellency. Although the reason for this is not clear, it is presumed that water repellency is improved by having a relatively long-chain alkyl group in the molecule.

The compounds of the present disclosure are useful as surface treatment agents. The surface treatment agent can be used, for example, for substrates in display devices such as touch panel displays, optical elements, semiconductor elements, building materials, automobile parts, nanoimprint technology, and the like. Furthermore, the surface treatment agent can be used for bodies, window glasses (windshields, side glasses, rear glasses), mirrors, bumpers, etc. of transportation equipment such as trains, automobiles, ships, and airplanes. Furthermore, the surface treatment agent can be used for outdoor articles such as building exterior walls, tents, solar power generation modules, sound insulation boards, and concrete; fishing nets, insect nets, and aquariums. Furthermore, the surface treatment agent can be used for various indoor equipment such as kitchens, bathrooms, washstands, mirrors, toilet peripheral parts; ceramics such as chandeliers and tiles; artificial marble, and air conditioners. Furthermore, the surface treatment agent can be used as an antifouling treatment for jigs, inner walls, piping, etc. in a factory. Furthermore, the surface treatment agent can be used for goggles, glasses, helmets, pachinko machines, textiles, umbrellas, play equipment, and soccer balls. Furthermore, the surface treatment agent can also be used as an adhesion prevention agent for various packaging materials such as food packaging materials, cosmetic packaging materials, and the inside of pots. In addition, surface treatment agents are used for medical applications such as car navigation systems, mobile phones, smartphones, digital cameras, digital video cameras, PDAs, portable audio players, car audio, game equipment, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastrocameras. It can be used for optical members such as appliances, copying machines, PCs, displays (for example, liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and antireflection films.

The disclosure of Japanese Patent Application No. 2022-069030 filed on April 19, 2022 is incorporated herein by reference in its entirety. In addition, all documents, patent applications, and technical standards mentioned herein are incorporated by reference to the same extent as if each individual document, patent application, and technical standard were specifically and individually indicated to be incorporated by reference. , incorporated herein by reference.

Claims

a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms;
(A) a linear alkylene group having 17 or more carbon atoms; (B) -CH=CH-; and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. at least one substructure comprising;
a reactive silyl group,
Compounds containing.
The compound according to claim 1, wherein the aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group is a benzene ring, a naphthalene ring, or a pyridine ring.
The aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group has 1 to 15 substituents, and each of the substituents is independently a halogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms. , an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -OCF 3 , -SF 5 , -OC(O)R s , -N(R s )C(O)R s , -NO 2 , -SO 2 R s , -NR s 2 , -C(O)OR s , -C(O)NR s 2 , and -C(O)R s , where R s The compound according to claim 1, wherein each independently represents a hydrogen atom or an alkyl group.
Compound represented by the following formula (1):
Ar-Z-Y 1 [-Si(R) n L 3-n ] g ...(1)
In formula (1),
Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms,
Z is a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. A divalent group containing at least one partial structure selected from
Y 1 is a single bond when g is 1, and is a (g + 1) valent linking group when g is 2 or more,
R is each independently a monovalent hydrocarbon group,
L is each independently a hydrolyzable group or a hydroxyl group,
n is an integer from 0 to 2,
g is an integer of 1 or more.
The compound according to claim 4, wherein in formula (1), g is an integer of 2 or more.
The compound according to claim 4, wherein the aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group is a benzene ring, a naphthalene ring, or a pyridine ring.
The aromatic ring having 4 to 16 carbon atoms in the monovalent aromatic ring group has 1 to 15 substituents, and each of the substituents independently represents a halogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms. , an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, -OCF 3 , -SF 5 , -OC(O)R s , -N(R s )C(O)R s , -NO 2 , -SO 2 R s , -NR s 2 , -C(O)OR s , -C(O)NR s 2 , and -C(O)R s , where R s 5. The compound according to claim 4, wherein each independently represents a hydrogen atom or an alkyl group.
Compound represented by the following formula (1-1):
Ar-Z-Y 11 (D) g1 ...(1-1)
In formula (1-1),
Ar is a monovalent aromatic ring group having a substituted or unsubstituted aromatic ring having 4 to 16 carbon atoms,
Z is a group consisting of (A) a linear alkylene group having 17 or more carbon atoms, (B) -CH=CH-, and (C) a substituted or unsubstituted divalent aromatic ring group having 4 to 16 carbon atoms. A divalent group containing at least one partial structure selected from
Y11 is a single bond when g1 is 1, and is a (g1+1) valent linking group when g1 is 2 or more,
Each D is independently -Q L -CH=CH 2 , where Q L is a single bond or a divalent linking group,
g1 is an integer of 1 or more.
A composition comprising the compound according to any one of claims 1 to 7 and a liquid medium.
A surface treatment agent comprising the compound according to any one of claims 1 to 7.
The surface treatment agent according to claim 10, further comprising a liquid medium.
A method for manufacturing an article, comprising performing a surface treatment on a base material using the surface treatment agent according to claim 10, and manufacturing an article in which a surface treatment layer is formed on the base material.
An article comprising a base material and a surface treatment layer disposed on the base material and surface treated with the surface treatment agent according to claim 10.
The article according to claim 13, wherein the article is an optical member.
The article according to claim 14, wherein the article is a display or a touch panel.