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

Abstract

Provided are: a novel compound capable of forming a surface treatment layer having excellent wear resistance; and the like. The compound according to the present disclosure is a compound containing the following group P and an organopolysiloxane residue. And a group P:-[Si (R1) 2-X] n1-Si (R1) 3. Wherein each X is independently an oxygen atom or a carbon atom, each R1 is independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group or a hydrocarbon group, at least four R1 in the R1 are a hydrolyzable group, a group having a hydrolyzable group or a hydroxyl group, and n1 is an integer of 1-3.

Description

Technical Field

[0001] This disclosure relates to compounds, compositions, surface treatment agents, articles, methods of manufacturing articles, and intermediates. Background Technology

[0002] In recent years, in order to improve appearance, visibility, and other properties, there has been a demand for technologies that make the surface of items less prone to fingerprints and easier to remove dirt. As a specific method, methods for surface treating the surface of items using surface treatment agents are known.

[0003] Patent document 1 describes specific silane compounds containing siloxanes having divalent linear organopolysiloxanes and hydrolyzable silanes.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: International Publication No. 2023 / 017830 Summary of the Invention

[0007] The problem the invention aims to solve

[0008] From the perspective of wear resistance and other factors, further improvements are needed for surface treatment agents.

[0009] This disclosure was made in view of this situation, and its purpose is to provide a novel compound, etc., capable of forming a surface treatment layer with excellent wear resistance.

[0010] Solution for solving the problem

[0011] This disclosure includes the following methods. [1]

[0013] A compound comprising the following groups: P and organopolysiloxane residues,

[0014] Group P: -[Si(R) 1 )2-X] n1 -Si(R 1 )3

[0015] in,

[0016] X can be an oxygen atom or a carbon atom independently.

[0017] R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group.

[0018] R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group.

[0019] n1 is an integer from 1 to 3. [2]

[0021] According to the compound described above [1], where n1 is 1. [3]

[0023] According to the compound described above [1], wherein the aforementioned group P is -[Si(OR)] 2 )2-O] n1 -Si(OR 2 )3,

[0024] in,

[0025] R 2 Each is an independent hydrocarbon group. [4]

[0027] According to the compound described above [2], wherein the aforementioned group P is -Si(OR) 2 )2-O-Si(OR 2 )3,

[0028] in,

[0029] R 2 Each is an independent hydrocarbon group. [5]

[0031] The compounds shown in formula (1) or formula (2) below.

[0032] [R 11 -(Q) r1 -Z 1 ] p1 -Q 1 -(J 1 ) n2 …Formula (1)

[0033] (J 1 ) n2 -Q 2 -Z 2 -Q 2 -(J 1 ) n2 …Formula (2)

[0034] in,

[0035] J 1 Each of them independently represents the following group P,

[0036] Group P: -[Si(R) 1 )2-X] n1 -Si(R 1 )3

[0037] X can be an oxygen atom or a carbon atom independently.

[0038] R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group.

[0039] R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group.

[0040] n1 is an integer from 1 to 3.

[0041] R 11 Each independently as (R 111 )3Si-, linear organopolysiloxane residues, cyclic organopolysiloxane residues, or cage-like organopolysiloxane residues,

[0042] R 111 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0043] Q can be independently -O- or -OC(=O)-.

[0044] r1 is independently either 0 or 1.

[0045] Z 1 Each can be independently a single bond, an alkylene group optionally having an ether-like oxygen atom, an organopolysiloxane group, or a combination of an alkylene group optionally having an ether-like oxygen atom and an organopolysiloxane group.

[0046] Z 2 It is an organopolysiloxane alkyl group, or a combination of an alkylene group having an ether-like oxygen atom and an organopolysiloxane alkyl group.

[0047] Q 1 It is a (p1+n2) valence linking group.

[0048] Q 2 Each is an independent linker with a valence of (1+n2).

[0049] p1 is an integer greater than or equal to 1.

[0050] Each of n2 is an integer greater than or equal to 1. [6]

[0052] According to the compound described above [5], where n2 is an integer from 1 to 3. [7]

[0054] According to the compounds described above [5] or [6], wherein the aforementioned Z 1 -(Si(R)8 )2-O) m -Si(R 8 )2-.

[0055] in,

[0056] R 8 Each is an independent hydrocarbon group.

[0057] m is a number greater than or equal to 1. [8]

[0059] According to any one of the compounds described in [5] to [7] above, wherein the aforementioned Z 2 -(Si(R) 8 )2-O) m -Si(R 8 )2-.

[0060] in,

[0061] R 8 Each is an independent hydrocarbon group.

[0062] m is a number greater than or equal to 1. [9]

[0064] A composition comprising any one of the compounds described in any one of [1] to [8] above and a liquid medium.

[10]

[0066] A surface treatment agent comprising any one of the compounds described in any of [1] to [8].

[11]

[0068] A surface treatment agent comprising any one of the compounds described in any one of [1] to [8] above and a liquid medium.

[12]

[0070] A method for manufacturing an article, wherein a surface treatment agent comprising any one of the compounds described in any one of [1] to [8] is used to surface treat a substrate to manufacture an article having a surface treatment layer formed on the substrate.

[13]

[0072] An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with a surface treatment agent comprising any one of the compounds described in any one of [1] to [8].

[14]

[0074] According to the aforementioned

[13] , it is an optical component.

[15]

[0076] According to the aforementioned

[13] , it is a display or touch panel.

[16]

[0078] An intermediate represented by the following formula (3),

[0079] H-[Si(R 1 )2-X] n1 -Si(R 1 )3…Equation (3)

[0080] in,

[0081] X can be an oxygen atom or a carbon atom independently.

[0082] R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group.

[0083] R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group.

[0084] n1 is an integer from 1 to 3.

[17]

[0086] According to the intermediate described above

[16] , where n1 is 1.

[0087] The effects of the invention

[0088] According to this disclosure, novel compounds and the like can be provided that can form surface treatment layers with excellent wear resistance. Detailed Implementation

[0089] In this specification, the numerical range represented by "~" contains the minimum and maximum values ​​before and after "~".

[0090] In the numerical ranges described in this specification, the upper or lower limit of a numerical range can be replaced by the upper or lower limit of other numerical ranges described in different stages. Furthermore, the upper or lower limit of the numerical range described in this specification can be replaced by the values ​​shown in the embodiments.

[0091] In this specification, "surface treatment layer" refers to a layer formed on the surface of a substrate through surface treatment.

[0092] In this specification, "Me" sometimes means methyl and "Et" sometimes means ethyl.

[0093] In this specification, when a compound or group is represented by a specific formula (X), the compound or group represented by formula (X) is sometimes referred to as compound (X) or compound X, and group (X) or group X, respectively.

[0094] It should be noted that when the same symbol exists in a chemical formula, the same symbol can be the same structure as each other, or it can be a structure that is different from each other within a specified range.

[0095] Unless otherwise specified, the bonding direction of the divalent groups described in this specification is not limited. For example, when Y in a compound represented by the formula "XYZ" is -COO-, Y can be -CO-O- or -O-CO-. In addition, the above compound can be "X-CO-OZ" or "XO-CO-Z".

[0096] [Compound]

[0097] The compounds disclosed herein contain the following groups P and organopolysiloxane residues.

[0098] Group P: -[Si(R) 1 )2-X] n1 -Si(R 1 )3

[0099] In this context, X is independently either an oxygen atom or a carbon atom, and R... 1 Each is independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group with a hydrolyzable group, or a hydroxyl group, where n1 is an integer from 1 to 3.

[0100] When the compounds of this disclosure are used as surface treatment agents, a surface treatment layer with excellent liquid repellency can be formed. The reason for this is not yet clear, but it is speculated as follows.

[0101] The compound containing the aforementioned group P exhibits high adhesion to the substrate, enabling the formation of a durable surface treatment layer on the substrate. Consequently, a surface treatment layer with excellent liquid repellency (water repellency, oil repellency) is formed.

[0102] <group P>

[0103] The compounds disclosed herein contain the aforementioned group P. The compound may contain only one group P or more than two groups P. For example, preferably 1 to 18 groups P, more preferably 2 to 12 groups P, and even more preferably 2 to 8 groups P.

[0104] When multiple groups P exist in a single molecule, these groups P can be identical or distinct. From the viewpoint of ease of obtaining raw materials and ease of manufacturing the compound, it is preferable that the multiple groups P are identical.

[0105] R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group.

[0106] Hydrolyzable groups are groups that become hydroxyl groups through hydrolysis. That is, Si-R 1 The hydrolyzable silane group shown is hydrolyzed to form a silanol group (Si-OH). The silanol group further reacts with each other to form a Si-O-Si bond. Alternatively, the silanol group can undergo a dehydration condensation reaction with silanol groups from oxides present on the substrate surface to form a Si-O-Si bond.

[0107] Examples of hydrolyzable groups include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, isocyanate groups (-NCO), and alkyl oxide-modified alkoxy groups.

[0108] The alkoxy group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. The aryloxy group preferably has 3 to 10 carbon atoms. The aryl group of the aryloxy group may also be a heteroaryl group. The halogen atom is preferably a chlorine atom. As an acyl group, an acyl group with 1 to 6 carbon atoms is preferred. As an acyloxy group, an acyloxy group with 1 to 6 carbon atoms is preferred.

[0109] The group having a hydrolyzable group can be, for example, the group having a hydrolyzable group illustrated above. The preferred group having a hydrolyzable group is -OL. A -L B L A It is an alkylene group, L B It is a hydrolyzable group. The alkylene group preferably has 1 to 10 carbon atoms. B The hydrolytic group represented is related to the above R 1 The meanings of the hydrolyzable groups are the same, and the preferred methods are also the same. A specific example of a group having a hydrolyzable group is -O-CH2CH2-OCH3.

[0110] In terms of the ease of compound preparation, R 1 The hydrolyzable groups or groups containing hydrolyzable groups are preferably alkoxy groups with 1 to 4 carbon atoms, epoxy-modified alkoxy groups, or halogen atoms. Considering the reduction of venting during coating and the superior storage stability of the compound, R... 1 Preferably, the alkoxy group has 1 to 4 carbon atoms, and more preferably, the ethoxy or methoxy group.

[0111] R 1Examples of hydrocarbon groups include alkyl, cycloalkyl, alkenyl, allyl, etc., and saturated hydrocarbon groups are preferred in terms of ease of synthesis, and alkyl groups are more preferred. The number of carbon atoms in the hydrocarbon group is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.

[0112] n1 is an integer from 1 to 3. From the perspective of ease of synthesis, it is preferably 1 to 2, and more preferably 1.

[0113] A group P possesses multiple R 1 In this group, at least four are hydrolyzable groups, groups having hydrolyzable groups, or hydroxyl groups. This allows group P to bond more firmly to the substrate, resulting in a surface treatment layer with excellent durability. From this perspective, the number of hydrolyzable groups, groups having hydrolyzable groups, and hydroxyl groups in group P is preferably 4 to 9, more preferably 4 to 7, and even more preferably 4 to 5.

[0114] It should be noted that multiple R molecules exist within a single molecule. 1 They can be the same or different from each other. For example, multiple R... 1 They can be the same hydrolyzable groups.

[0115] X can be an oxygen atom or a carbon atom. Here, a carbon atom in X refers to Si atoms connected to each other by one carbon atom, and X can be -CH2-, -C(CH3)2-, etc. From the viewpoint of the durability of the surface treatment layer, X is preferably an oxygen atom, -CH2- or -C(CH3)2-, more preferably an oxygen atom or -CH2-, and even more preferably an oxygen atom.

[0116] From the perspective of excellent durability of the surface treatment layer, the group P is preferably -[Si(OR)] 2 )2-O] n1 -Si(OR 2 )3, wherein, particularly preferred is -Si(OR) with n1=1. 2 )2-O-Si(OR 2 3. Among them, R 2 Each is independently a hydrocarbon group. Examples of such hydrocarbon groups include alkyl, cycloalkyl, alkenyl, and allyl groups; from the perspective of ease of synthesis, saturated hydrocarbon groups are preferred, and alkyl groups are more preferred. R 2 The number of carbon atoms is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 to 2.

[0117] Specific examples of the group P include -Si(OCH3)2-O-Si(OCH3)3, -Si(OCH3)2-CH2-Si(OCH3)3, -Si(OCH3)2-C(CH3)2-Si(OCH3)3, -Si(OCH2CH3)2-O-Si(OCH3)3, -Si(OCH3)2-O-Si(OCH2CH3)3 , -Si(OCH2CH3)2-O-Si(OCH2CH3)3, -Si(OCH2CH3)2-CH2-Si(OCH3)3, -Si(OCH3)2-CH2-Si(OCH2CH3)3, -Si(OCH2CH3)2-CH2-Si(OCH2CH3)3, -Si(OCH2CH3)2-C(CH3)2-Si (OCH3)3, -Si(OCH3)2-C(CH3)2-Si(OCH2CH3)3, -Si(OCH2CH3)2-C(CH3)2-Si(OCH2CH3)3, -Si(OH)2-O-Si(OH)3, -Si(OH)2-O-Si(OCH3)3, -Si(OCH3)2-O-Si(OH)3, -Si(O H)2-CH2-Si(OH)3, -Si(OH)2-CH2-Si(OCH3)3, -Si(OCH3)2-CH2-Si(OH)3, -Si(OH)2-C(CH3)2-Si(OH)3, -Si(OH)2-C(CH3)2-Si(OCH3)3, -Si(OCH3)2-C(CH3)2-Si(OH)3.

[0118] <organopolysiloxane residues>

[0119] The compounds disclosed herein, by having organopolysiloxane residues, are capable of forming surface treatment layers with excellent liquid repellency. Organopolysiloxane residues represent groups having a -Si-O- backbone; specifically, examples include R... (described later). 11 The same group.

[0120] <Compound(1), Compound(2)>

[0121] The compounds disclosed herein are those represented by formula (1) or formula (2) below.

[0122] [R 11 -(Q) r1 -Z 1 ] p1 -Q 1 -(J 1 ) n2 …Formula (1)

[0123] (J 1 )n2 -Q 2 -Z 2 -Q 2 -(J 1 ) n2 …Formula (2)

[0124] Among them, J 1 Each of these is independently represented by the aforementioned group P, and repeated descriptions are omitted.

[0125] Additionally, R 11 Each independently as (R 111 )3Si-, linear organopolysiloxane residues, cyclic organopolysiloxane residues, or cage-like organopolysiloxane residues, R 111 Each is independently a hydrocarbon group or a trialkylsilyloxy group, Q is independently -O- or -OC(=O)-, r1 is independently 0 or 1, Z 1 Each is independently a single bond, an alkylene group optionally having an ether-like oxygen atom, an organopolysiloxane group, or a combination of an alkylene group optionally having an ether-like oxygen atom and an organopolysiloxane group, Z 2 Q is an organopolysiloxane, or a combination of an alkylene group having an ether-like oxygen atom and an organopolysiloxane, Q 1 Q is a (p1+n2) valence linking group. 2 It is a (1+n2) valence linker, where p1 is an integer greater than or equal to 1 and n2 is an integer greater than or equal to 1.

[0126] R 11 Each independently as (R 111 )3Si-, linear organopolysiloxane residues, cyclic organopolysiloxane residues, or cage-like organopolysiloxane residues, R 111 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0127] As R 111 The hydrocarbon group in R can include alkyl, cycloalkyl, aryl, etc. From the perspective of ease of synthesis, saturated hydrocarbon groups are preferred, and alkyl groups are even more preferred. 111 The number of carbon atoms is preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 2.

[0128] R 111 The trialkylsilyloxy group in the preferred form is R. 40 The group represented by 3SiO-. Wherein, R 40 Each is an independent hydrocarbon group. R 40 The hydrocarbon group in R is preferably alkyl or aryl, more preferably alkyl. 40 The number of carbon atoms is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 2.

[0129] R11 The linear organopolysiloxane residues in it are preferably the following groups (A2).

[0130]

[0131] Among them, R 5 Each is an independent hydrocarbon group, and k2 is a number greater than or equal to 1.

[0132] R 5 The hydrocarbon group is preferably alkyl or aryl, more preferably alkyl. 5 The number of carbon atoms is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 2. As R 5 Specific examples of hydrocarbon groups in this context include -CH3, -CH2CH3, and -C(CH3)3.

[0133] k2 can be a number greater than or equal to 1, preferably a number between 2 and 500, and more preferably a number between 3 and 300.

[0134] R 11 The cyclic organopolysiloxane residues in it are preferably the following groups (A3).

[0135]

[0136] Among them, R 6 Each is independently a hydrocarbon group, a hydrocarbon group with substituents, or a trialkylsilyloxy group, and t3 is a number from 1 to 4.

[0137] As R 6 The hydrocarbon group in the form is preferably alkyl or aryl, more preferably alkyl.

[0138] The alkyl group can be any of the following: straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably straight-chain alkyl. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 8, and even more preferably 1 to 4. The same applies to the alkyl group in the trialkylsilyloxy group.

[0139] Among the substituents in hydrocarbon groups, examples of substituents include halogen atoms, hydroxyl groups, alkoxy groups, trialkylsiloxy groups, trialkylsilyl groups, amino groups, nitro groups, cyano groups, sulfonyl groups, and trifluoromethyl groups.

[0140] Specific examples of cyclic organopolysiloxane residues include the following groups.

[0141]

[0142]

[0143] R 11 The cage-like organopolysiloxane residues in the sample are preferably the following groups (A4).

[0144]

[0145] Among them, R 7 Each is independently a hydrocarbon group, a hydrocarbon group with substituents, or a trialkylsilyloxy group.

[0146] As R 7 The hydrocarbon group in the form is preferably alkyl or aryl, more preferably alkyl.

[0147] The alkyl group can be any of the following: straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably straight-chain alkyl. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 8, and even more preferably 1 to 4. The same applies to the alkyl group in the trialkylsilyloxy group.

[0148] Among the substituents in hydrocarbon groups, examples of substituents include halogen atoms, hydroxyl groups, alkoxy groups, trialkylsiloxy groups, trialkylsilyl groups, amino groups, nitro groups, cyano groups, sulfonyl groups, and trifluoromethyl groups.

[0149] Specific examples of cage-like organopolysiloxane residues include the following groups.

[0150]

[0151] Q is independently -O- or -OC(=O)-, and r1 is 0 or 1. Therefore, when r1 is 0, it is a single bond.

[0152] Z 1 Each can be independently a single bond, an alkylene group optionally having an ether-like oxygen atom, an organopolysiloxane group, or a combination of an alkylene group optionally having an ether-like oxygen atom and an organopolysiloxane group.

[0153] Z 2 It is an organopolysiloxane or an optional combination of an alkylene group having an ether-like oxygen atom and an organopolysiloxane.

[0154] The following is based on Z 1 To illustrate, let's take a look at Z. 2 This can be understood as Z below 1 The description specifies that it is an organopolysiloxane, or a combination of an alkylene group having an ether-like oxygen atom and an organopolysiloxane.

[0155] The alkylene group having an ether-like oxygen atom may be selected as long as it has 1 or more carbon atoms, and in terms of water repellency, it is preferably 2 or more carbon atoms, more preferably 4 or more. There is no particular upper limit on the number of carbon atoms in the alkylene group, but it is 30 or less, preferably 24 or less. The alkylene group having an ether-like oxygen atom in the compounds disclosed herein may be any of the following: linear, branched, or cyclic, preferably linear or branched, more preferably linear.

[0156] The organopolysiloxane alkyl group is preferably the following group (A6).

[0157]

[0158] Among them, R 8 Each is an independent hydrocarbon group, k6 is a number greater than or equal to 1, j6 is 0 or 1, * represents the Q-side linkage, and ** represents the Q-side linkage. 1 The connection key on the side. It should be noted that Z... 2 In the case of *, * represents a Q 2 The side connection key, ** is another Q 2 The connection key on the side.

[0159] As R 8 The hydrocarbon group in R can include alkyl, cycloalkyl, alkenyl, allyl, etc. From the perspective of ease of synthesis, saturated hydrocarbon groups are preferred, and alkyl groups are even more preferred. 8 The number of carbon atoms is preferably 1 to 6, more preferably 1 to 3, and more preferably 1 or 2.

[0160] k6 can be a number greater than or equal to 1, preferably a number between 2 and 500, and more preferably a number between 3 and 300.

[0161] From the perspective of the durability of the surface treatment layer, Z 1 and Z 2 Preferably -(Si(R) 8 )2-O) m -Si(R 8 )2-. Where m has the same meaning as k6 above, R 8 Each is an independent hydrocarbon group, as defined above.

[0162] Examples of combinations of alkylene groups having optional ether-containing oxygen atoms and organopolysiloxane groups include the following groups (B1) to (B4).

[0163] *-R Si -Ak 1 -** …(B1)

[0164] *-Ak 1 -R Si -** …(B2)

[0165] *-Ak 1 -R Si -Ak 1 -** …(B3)

[0166] *-R Si -Ak 1 -R Si -** …(B4)

[0167] Among them, Ak 1 Each is independently an alkylene group, R Si Each of these is an independent group (A6), * represents the linking bond on the Q side, and ** represents the Q group. 1 The connection key on the side. It should be noted that Z... 2 In the case of *, * represents a Q 2 The side connection key, ** is another Q 2 The connection key on the side.

[0168] Ak 1 The alkylene group in the alkylene group only needs to have 1 or more carbon atoms, but for water repellency, it is preferably 2 or more carbon atoms, more preferably 4 or more. There is no particular upper limit to the number of carbon atoms in the alkylene group, but it is 30 or less, preferably 24 or less. Ak 1 The alkylene groups in the form are preferably linear or branched, and more preferably linear.

[0169] The combination of alkylene and organopolysiloxane, or the combination of alkylene and organopolysiloxane, is preferably composed of group (B1), group (B3) or group (B4) from the perspective of water repellency, more preferably group (B1) or group (B4), and further preferably group (B1) from the perspective of ease of manufacture.

[0170] Q 1 Q is a (p1+n2) valence linking group. 2 It is a (1+n2) valence linking group. Hereinafter, Q will be used as the reference. 1 To illustrate, let's look at Q. 2 This can be understood as being in the following Q 1 The description specifies p1 as 1.

[0171] Q 1 Any group that does not impair the effects of this disclosure may be used. Examples include alkylene groups, carbon atoms, nitrogen atoms, silicon atoms, organopolysiloxanes having optional ethereal oxygen atoms or divalent alkyl groups, organopolysiloxanes with 2 to 8 valent alkyl groups, and groups from (3-1A), (3-1B), (3-1A-1) to (3-1A-7) described below, after removing J. 1 (i.e., group P) is a group obtained from it.

[0172] Among them, in Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, Q 1 The and Z 1 The terminal of the bonded side is not an alkylene group. Additionally, in Z... 1 In the case of organopolysiloxane, Q 1 The and Z 1 The end of the bonded side is not an organopolysiloxane alkyl group.

[0173] In addition, Q 1 It can be the groups (g2-1) to (g2-14) described later.

[0174] p1 is an integer greater than or equal to 1. Considering the superior water repellency of the surface treatment layer, p1 is preferably 1 to 6, and more preferably 1 to 4.

[0175] n2 is an integer greater than or equal to 1. From the viewpoint of superior wear resistance of the surface treatment layer, n2 is preferably 1 to 15, more preferably 1 to 6, even more preferably 2 to 4, and particularly preferably 2 or 3.

[0176] -Q in equation (1) 1 -(J 1 ) n2 The indicated group is preferably the group (3-1A) or (3-1B) described below, more preferably the group (3-1A).

[0177] -Q a -X 31 (-Q b -J 1 ) h (-R 31 ) i …(3-1A)

[0178] -Q c -[CH2C(R 32 (-Q) d -J 1 )] y -R 33 …(3-1B)

[0179] Q a It is a single bond or a divalent linker.

[0180] Among them, in Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, Q a The terminal end of the side bonded to Z is not an alkylene group. Additionally, in Q... 1 In the case of organopolysiloxane, Q aThe end of the side bonded to Z is not an organopolysiloxane.

[0181] Examples of divalent linking groups include divalent hydrocarbon groups, divalent heterocyclic groups, -O-, -S-, -SO2-, and -N(R) groups. d -, -C(O)-, -Si(R) a )2-, and groups formed by combining two or more of them.

[0182] The aforementioned divalent hydrocarbon group can be a divalent saturated hydrocarbon group, a divalent aromatic hydrocarbon group, an alkenyl group, or an alkyne group. The divalent saturated hydrocarbon group can be linear, branched, or cyclic; for example, alkylene groups are listed. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, even more preferably 4 to 20, and particularly preferably 5 to 15. Furthermore, as a divalent aromatic hydrocarbon group, a group with 5 to 20 carbon atoms is preferred; for example, phenylene groups are listed. In addition, it can also be an alkenyl group or an alkyne group with 2 to 20 carbon atoms.

[0183] The above R a It is an alkyl group (preferably with 1 to 10 carbon atoms) or a phenyl group. The above R... d It is a hydrogen atom or an alkyl group (preferably with 1 to 10 carbon atoms).

[0184] It should be noted that, for example, the groups formed by combining two or more of these can be: -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 )-、-SO2N(R d )-、-N(R d SO2-, possessing -C(O)N(R) d )-alkylene groups, having -N(R d )C(O)- alkylene groups, having -OC(O)N(R d Alkylenes with - )-, Alkylenes with ether-like oxygen atoms, Alkylenes with -S-, Alkylenes with -OC(O)-, Alkylenes with -C(O)O-, Alkylenes with -C(O)S-, Alkylenes with -N(R)- d )-alkylene groups, having -N(R d )C(O)N(R d )-alkylene groups, having -SO2N(R d )-alkylene, alkylene-Si(R) a)2-Phenylidene-Si(R a )2.

[0185] Among them, Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, Q a Preferably, divalent hydrocarbon groups other than alkylene groups, divalent heterocyclic groups, -O-, -S-, -SO2-, and -N(R) groups are used. d -, -C(O)-, -Si(R) a )2-, -OC(O)-, -C(O)O-, -C(O)S-, -C(O)N(R d )-、-N(R d )C(O)-、-N(R d )C(O)N(R d )-、-N(R d )C(O)O-、-OC(O)N(R d )-、-SO2N(R d )-、-N(R d SO2-, possessing -C(O)N(R) d )-alkylene groups, having -N(R d )C(O)- alkylene groups, having -OC(O)N(R d Alkylenes with - )-, Alkylenes with ether-like oxygen atoms, Alkylenes with -S-, Alkylenes with -OC(O)-, Alkylenes with -C(O)O-, Alkylenes with -C(O)S-, Alkylenes with -N(R)- d )-alkylene groups, having -N(R d )C(O)N(R d )-alkylene groups, or those having -SO2N(R d )- alkylene groups, more preferably -OC(O)-, having -C(O)N(R d )-alkylene groups, having -OC(O)N(R d Alkylenes with -S-, alkylenes with -C(O)O-, alkylenes with -C(O)S-, and alkylenes with -N(R) d )-alkylene groups, or those having -N(R d )C(O)N(R d Alkylenes having -C(O)O-, or alkylenes having -C(O)N(R)- d )-alkylene groups.

[0186] Z 1 When it is an organopolysiloxane, Q aPreferably, it is a divalent hydrocarbon group, a divalent heterocyclic group, -SO2-, -C(O)-, or -Si(R)-. a )2-, -C(O)O-, -C(O)S-, -C(O)N(R d )-、-SO2N(R d -、Having -C(O)N(R) d Alkylenes with -C(O)O-, Alkylenes with -SO2N(R)- d )-alkylene, alkylene-Si(R) a )2-Phenylidene-Si(R a )2, more preferably -C(O)-.

[0187] In equation (3-1A), X 31 It can be a single bond, alkylene group, carbon atom, nitrogen atom, silicon atom, organopolysiloxane group with 2 to 8 valences, or a ring group with (h+i+1) valences.

[0188] Among them, in Z 1 The and Q 1 The terminal of the bonded side is an alkylene group and Q a In the case of a single key, X 31 The and Z 1 The terminal of the bonded side is not an alkylene group.

[0189] Additionally, in Z 1 It is an organopolysiloxane alkyl group, and Q a In the case of a single key, X 31 The terminal end of the side bonded to Z is not an organopolysiloxane. In other cases, X 31 The terminal end can be alkylene or organopolysiloxane.

[0190] It should be noted that the aforementioned alkylene groups may optionally have -O-, silylene backbone groups, divalent organopolysiloxane groups, or dialkylsilyl groups. The alkylene groups may optionally have a plurality of groups selected from the group consisting of -O-, silylene backbone groups, divalent organopolysiloxane groups, and dialkylsilyl groups.

[0191] X 31 The alkylene group represented preferably has 1 to 20 carbon atoms, more preferably 1 to 10.

[0192] Examples of divalent to octagonal organopolysiloxanes include divalent organopolysiloxanes and (w+1) valent organopolysiloxanes, which will be discussed later.

[0193] In equation (3-1A), X 31 When Q is a group with a ring having a valence of (h+i+1), a 、(-Qb -J 1 ) and R 31 It is directly bonded to the atoms that make up the ring. This ring is a ring other than an organopolysiloxane ring.

[0194] X 31 The ring can be any of the following: monocyclic, fused polycyclic, bridged, spirocyclic, and aggregated polycyclic. The atoms constituting the ring can be a carbon ring composed solely of carbon atoms, or a heterocycle composed of heteroatoms with a valence of 2 or higher and carbon atoms. Furthermore, the bonds between the atoms constituting the ring can be single bonds or multiple bonds. Moreover, the ring can be aromatic or non-aromatic.

[0195] As a monocyclic ring, 4-membered to 8-membered rings are preferred, and 5-membered and 6-membered rings are more preferred. As a fused polycyclic ring, a fused polycyclic ring formed by the fusion of two or more 4-membered to 8-membered rings is preferred, a fused polycyclic ring formed by the bonding of two or three rings selected from 5-membered and 6-membered rings is more preferred, and a fused polycyclic ring formed by the bonding of one or two rings selected from 5-membered and 6-membered rings with one 4-membered ring is more preferred. As a bridging ring, a bridging ring with a 5-membered or 6-membered ring as the largest ring is preferred, and a spirocyclic ring formed by two 4-membered to 6-membered rings is preferred. As an aggregated polycyclic ring, an aggregated polycyclic ring formed by the bonding of two or three rings selected from 5-membered and 6-membered rings through single bonds, one to three carbon atoms, or one heteroatom with a valence of 2 or 3 is preferred. It should be noted that in aggregated polycyclic rings, it is preferred that each ring is bonded with a Q. a 、(-Q b -J 1 ) and R 31 Any one of (when i=1 or higher).

[0196] Nitrogen, oxygen, and sulfur atoms are preferred as heteroatoms constituting the aforementioned ring, and nitrogen and oxygen atoms are more preferred. The number of heteroatoms constituting the ring is preferably three or less. Furthermore, when the number of heteroatoms constituting the ring is two or more, these heteroatoms can be different.

[0197] As X 31 The ring in the compound is preferably selected from the group consisting of aliphatic rings with 3 to 8 members, benzene rings, heterocyclic rings with 3 to 8 members, fused rings formed by 2 or 3 of these rings, bridged rings with 5 or 6 members as the largest ring, and polycyclic rings consisting of alkylene groups, oxygen atoms or sulfur atoms with 2 or more of these rings and single bonds as the connecting groups.

[0198] Preferred rings are benzene rings, 5- or 6-membered aliphatic rings, 5- or 6-membered heterocycles having nitrogen or oxygen atoms, and fused rings consisting of 5- or 6-membered carbon rings and 4- to 6-membered heterocycles.

[0199] Specific examples of rings include the following rings, as well as 1,3-cyclohexadiene rings, 1,4-cyclohexadiene rings, anthracene rings, cyclopropane rings, decahydronaphthalene rings, norbornene rings, norbornadiene rings, furan rings, pyrrole rings, thiophene rings, pyrazine rings, morpholine rings, aziridine rings, isoquinoline rings, oxazole rings, isoxazole rings, thiazole rings, imidazole rings, pyrazole rings, pyran rings, pyridazine rings, pyrimidine rings, and indene rings. It should be noted that rings with an oxygen group (=O) are also shown below.

[0200]

[0201] X 31 The non-ring-forming connecting bonds of the atoms forming the ring are with Q. a 、(-Q b -J 1 ) or R 31 Linking bonds. In the presence of remaining linking bonds, these bonds are bonded to hydrogen atoms or substituents. Examples of such substituents include halogen atoms, alkyl groups (optionally containing an ether-like oxygen atom between carbon atoms), cycloalkyl groups, alkenyl groups, allyl groups, alkoxy groups, and oxo groups (=O).

[0202] In addition, one carbon atom forming the ring has two atoms related to Q. a 、(-Q b -J 1 ) or R 31 In the case of a bonded linkage, a Q can be bonded to this single carbon atom. a and(-Q b -J 1 It can also bond two (-Q) bonds. b -J 1 ). Preferred Q a With (-Q) b -J 1 ) or R 31 Bonded to different ring-forming atoms. h (-Q) b -J 1 Each of these atoms can bond to different cyclic atoms, and two of them can bond to one cyclic carbon atom, resulting in two (-Q) bonds. b -J 1 The cyclic carbon atoms can exist in more than two positions. (i R) 31 It can bond to different cyclic atoms, and two of them can bond to one cyclic carbon atom, thus forming two R bonds. 31 There can be more than two cyclic carbon atoms.

[0203] From the perspective of improving the wear resistance of the surface treatment layer, X 31Preferably, the group consists of carbon atoms, nitrogen atoms, silicon atoms, organopolysiloxane groups with 4 to 8 valences, or groups with a ring having a (h+i+1) valence, with carbon atoms being more preferred.

[0204] In formula (3-1A), Q b It is a single bond or a divalent linker. The definition of a divalent linker is the same as that of Q above. a The definitions described herein are the same.

[0205] Among them, in Z 1 The and Q 1 The terminal of the bonded side is an alkylene group, and Q a and X 31 In the case of a single key, Q b The and Z 1 The terminal of the bonded side is not an alkylene group. Additionally, in Z... 1 It is an organopolysiloxane alkyl group, and Q a and X 31 In the case of a single key, Q b The terminal end of the side bonded to Z is not an organopolysiloxane alkyl group. In cases other than those described above, Q... b The terminal end can be alkylene or organopolysiloxane.

[0206] Among them, Q b Preferably, the alkylene group has an ether-like oxygen atom. The number of carbon atoms in the alkylene group is preferably 1 to 30, more preferably 1 to 20, even more preferably 2 to 20, and can be 2 to 10, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0207] In equation (3-1A), R 31 It can be a hydrogen atom, a hydroxyl group, or an alkyl group. The alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3, and even more preferably 1.

[0208] X 31 When the bond is a single bond or an alkylene group, h is 1 and i is 0.

[0209] X 31 When the atom is nitrogen, h is an integer from 1 to 2, and i is an integer from 0 to 1, satisfying h + i = 2.

[0210] X 31 When the atoms are carbon or silicon, h is an integer from 1 to 3, and i is an integer from 0 to 2, satisfying h + i = 3.

[0211] In X 31 In the case of organopolysiloxanes with a valence of 2 to 8, h is an integer from 1 to 7, and i is an integer from 0 to 6, satisfying h + i = 1 to 7.

[0212] X 31 When the group is a cyclic group with a valence of (h+i+1), h is an integer from 1 to 7 and i is an integer from 0 to 6, satisfying h+i=1~7.

[0213] (-Q b -J 1 When there are two or more (-Q) b -J 1 They can be the same or different.

[0214] R 31 When there are two or more, the two or more (-R) 31 They can be the same or different.

[0215] From the perspective of improving the wear resistance of the surface treatment layer, i is preferably 0.

[0216] In formula (3-1A), Q a X 31 and Q b When it is a single bond, J 1 With Z 1 Direct bonding, Z 1 It is an alkylene group.

[0217] In equation (3-1B), Q c It is a single bond or a divalent linker.

[0218] Among them, in Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, Q c The and Z 1 The terminal end of the bonded side is not an alkylene group. Z 1 When it is an organopolysiloxane, Q c The end of the side bonded to Z is not an organopolysiloxane.

[0219] The definition of a divalent linker is the same as that of Q above. a The definitions described herein are the same.

[0220] In equation (3-1B), R 32 The atom is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; for ease of compound production, a hydrogen atom is preferred.

[0221] As an alkyl group, methyl is preferred.

[0222] In equation (3-1B), Q d It is a single bond or an alkylene group. The alkylene group preferably has 1 to 10 carbon atoms, more preferably 1 to 6. From the perspective of ease of compound preparation, Q... d Preferably, it is a single bond or CH2-.

[0223] In equation (3-1B), R 33 The atom can be a hydrogen atom or a halogen atom; from the perspective of ease of compound production, a hydrogen atom is preferred.

[0224] y is an integer from 1 to 10, preferably an integer from 1 to 6.

[0225] Two or more [CH2C(R)] 32 (-Q) d -J 1 The characters can be the same or different.

[0226] As the group (3-1A), the following groups (3-1A-1) to (3-1A-7) are preferred.

[0227] -(X 32 ) s1 -Q b1 -J 1 …(3-1A-1)

[0228] -(X 33 ) s2 -Q a2 -N[-Q b2 -J 1 ]2…(3-1A-2)

[0229] -Q a3 -Si(R g )[-Q b3 -J 1 ]2…(3-1A-3)

[0230] -[Q e ] s4 -Q a4 -(O) t4 -C[-(O) u4 -Q b4 -J 1 ] 3-w1 (-R 31 ) w1 …(3-1A-4)

[0231] -Q a5 -Si[-Q b5 -J 1 ]3…(3-1A-5)

[0232] -[Q e ] v -Q a6 -Z a [-Q b6 -J 1 ] w2…(3-1A-6)

[0233] -[Q e ] s4 -Q a4 -(O) t4 -Z c [-(OQ b4 ) u4 -J 1 ] w3 (-OH) w4 …(3-1A-7)

[0234] Among them, in Z 1 The and Q 1 When the terminal side of the bond is an alkylene group, the groups (3-1A-1)~(3-1A-7) with Z 1 The terminal of the bonded side is not an alkylene group. Additionally, in Z... 1 In the case of organopolysiloxane, the groups (3-1A-1)~(3-1A-7) with Z 1 The end of the bonded side is not an organopolysiloxane alkyl group.

[0235] Wherein, group (3-1A) is preferably group (3-1A-4).

[0236] In group (3-1A-1), X 32 -O-, -S-, -N(R) d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-、-N(R d SO2-, -N(R) d )C(O)-、-N(R d )C(O)N(R d )-、-OC(O)N(R d - or -C(O)N(R) d )-(where N and Q in the formula b1 (bonding).

[0237] R d The definition is as described above.

[0238] s1 is either 0 or 1.

[0239] Among them, Z 1 The and Q 1 When the terminal of one side of the bond is an alkylene group, X 32 Preferably -O-, -S-, -N(R) d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-、-N(Rd SO2-, -N(R) d )C(O)-、-N(R d )C(O)N(R d )-、-OC(O)N(R d - or -C(O)N(R) d -, more preferably -O-, -S-, -N(R) d -, -C(O)O-, -C(O)S-, -N(R) d )C(O)N(R d )-、-OC(O)N(R d - or -C(O)N(R) d -, more preferably -C(O)O- or -C(O)N(R) d )-.

[0240] Z 1 When X is an organopolysiloxane alkyl group, 32 Preferably -C(O)O-, -C(O)S-, -SO2N(R) d - or -C(O)N(R) d )-, more preferably -C(O)-.

[0241] Q b1 It can be a single bond or an alkylene group. It should be noted that the alkylene group may optionally have an -O-, a silylene skeleton group, or a dialkylsilyl group. The alkylene group may optionally have a plurality of groups selected from the group consisting of -O-, a silylene skeleton group, a divalent organopolysiloxane group, and a dialkylsilyl group.

[0242] It should be noted that when the alkylene group has -O-, silylene skeleton group, divalent organopolysiloxane or dialkylsilyl group, these groups are preferably present between carbon atoms.

[0243] Q b1 The alkylene group represented preferably has 1 to 30 carbon atoms, more preferably 1 to 20, even more preferably 2 to 20, and particularly preferably 2 to 6. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0244] Among them, in Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, s1 is preferably 1, Q b1 Preferably, it is an alkylene group having 2 to 6 carbon atoms.

[0245] Z 1 When s1 is an organopolysiloxane alkyl group, s1 is preferably 0, Q is preferably 0. b1 Alkylenes with 2 to 6 carbon atoms are preferred.

[0246] Z 1 and A 11 When the terminal side of the bond is an alkylene group, the following groups can be cited as specific examples of the group (3-1A-1). In the following formulas, * indicates a bond with Z. 1 The bonding positions.

[0247]

[0248] Z 1 When the group is an organopolysiloxane alkyl group, the following groups can be cited as specific examples of the group (3-1A-1). In the following formulas, * indicates a group related to Z. 1 The bonding positions.

[0249]

[0250] In group (3-1A-2), X 33 -O-, -S-, -N(R) d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-、-N(R d SO2-, -N(R) d )C(O)-、-N(R d )C(O)N(R d )-、-OC(O)N(R d - or -C(O)N(R) d )-.

[0251] R d The definition is as described above.

[0252] s2 is either 0 or 1. From the perspective of ease of compound production, s2 is preferably 0.

[0253] Among them, in Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, X 33 Preferably -O-, -S-, -N(R) d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-、-N(R d SO2-, -N(R) d )C(O)-、-N(R d )C(O)N(R d )-、-OC(O)N(R d - or -C(O)N(R) d )-.

[0254] When Z is an organopolysiloxane alkyl group, X33 Preferably -C(O)O-, -C(O)S-, -SO2N(R) d - or -C(O)N(R) d )-.

[0255] Q a2 It is a single bond, alkylene, -C(O)-, or an etheric oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms, -C(O)-, -C(O)O-, -OC(O)-, -C(O)N(R) d )-、-N(R d )C(O)-、-N(R d )C(O)N(R d )-、-N(R d )C(O)O-、-OC(O)N(R d )-、-SO2N(R d )-、-N(R d SO2-, -C(O)N(R) d () or -NH- groups.

[0256] Q a2 The alkylene group represented preferably has 1 to 20 carbon atoms, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 3.

[0257] By Q a2 The alkylene groups having two or more carbon atoms have etheric oxygen atoms between their carbon atoms, -C(O)-, -C(O)O-, -OC(O)-, or -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 )-、-SO2N(R d )-、-N(R d SO2-, -C(O)N(R) d The number of carbon atoms in the )- or -NH- group is preferably 2 to 10, more preferably 2 to 6.

[0258] From the perspective of ease of compound production, Q a2 Single bonds are preferred.

[0259] Q b2 It is an alkylene group, or an organopolysiloxane group having a divalent oxygen atom or -NH- between carbon atoms in an alkylene group having two or more carbon atoms.

[0260] Q b2 The alkylene group represented preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0261] Q b2 The number of carbon atoms in the alkylene group having a divalent organopolysiloxane, ether oxygen atom, or -NH- group between carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0262] As Q b2 From the perspective of ease of compound production, -CH2CH2CH2- and -CH2CH2OCH2CH2CH2- (where the right side is bonded to Si) are preferred.

[0263] 2 [-Q] b2 -J 1 They can be the same or different.

[0264] Z 1 The and Q 1 When the terminal of one side of the bond is an alkylene group, the following groups can be cited as specific examples of the group (3-1A-2). In the following formulas, * indicates the bond position with Z. Additionally, in the formula, the bond position with J... 1 Bonded (CH2) α In this compound, α represents the number of methylene groups, preferably 1 to 30, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Additionally, the aforementioned number of carbon atoms can be 1 to 10. The multiple α groups in the same compound can be the same or different, but are preferably the same. For example, the multiple α groups in the same compound may all be 2, 3, 8, 9, and 11, and the same applies below.

[0265]

[0266] Z 1 When the group is an organopolysiloxane alkyl group, the following groups can be cited as specific examples of the group (3-1A-2). In the following formulas, * indicates a group related to Z. 1 The bonding positions.

[0267]

[0268] In group (3-1A-3), Q a3 It is a single bond, or optionally an alkylene group with an ether-like oxygen atom. From the perspective of ease of compound preparation, Q... a3 Single bonds are preferred.

[0269] The number of carbon atoms in the alkylene group having an ether-like oxygen atom is preferably 1 to 10, and particularly preferably 2 to 6.

[0270] R g It can be a hydrogen atom, a hydroxyl group, or an alkyl group.

[0271] As R g From the viewpoint of easy compound production, hydrogen atoms or alkyl groups are preferred. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 4, and even more preferably methyl.

[0272] Q b3 It is an alkylene group, or an organopolysiloxane group with an ether oxygen atom or a divalent oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms.

[0273] Q b3 The alkylene group represented preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0274] By Q b3 The number of carbon atoms in the alkylene group having an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0275] From the perspective of ease of compound production, Q b3 Preferably, it is -CH2CH2-, -CH2CH2CH2-, or -CH2CH2CH2CH2CH2CH2CH2CH2-.

[0276] 2 [-Q] b3 -J 1 They can be the same or different.

[0277] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, the following groups can be cited as specific examples of the group (3-1A-3). In the following formulas, * indicates the bonded position with Z.

[0278]

[0279] Z 1 When the group is an organopolysiloxane alkyl group, the following groups can be cited as specific examples of the group (3-1A-3). In the following formulas, * indicates a group related to Z. 1 The bonding positions.

[0280]

[0281] In group (3-1A-4), Q e is -C(O)O-, -SO2N(R d )-、-N(R d SO2-, -N(R) d C(O)- or -C(O)N(R) d )-.

[0282] R 31 The definition is as described above. When w1 is 1 or 2, R... 31 Hydrogen atoms are preferred.

[0283] s4 is either 0 or 1.

[0284] Q a4 It is a single bond or an alkylene group optionally having an ether-like oxygen atom.

[0285] The number of carbon atoms in the alkylene group having an ether-like oxygen atom is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 3.

[0286] t4 is 0 or 1 (where Q is 0 or 1). a4 (0 when it is a single bond).

[0287] As -Q a4 -(O) t4 From the perspective of ease of compound preparation, when s4 is 0, single bonds, -CH2O-, -CH2OCH2-, -CH2OCH2CH2O-, -CH2OCH2CH2OCH2-, and -CH2OCH2CH2CH2CH2OCH2- are preferred (where the left side is related to (XO)). m (For bonding, when s4 is 1, single bonds, -CH2-, and -CH2CH2- are preferred.)

[0288] Q b4 The alkylene group is optionally -O- or -C(O)N(R) d )-(R d (as defined above), silymine skeleton group, divalent organopolysiloxane or dialkylsilyl group.

[0289] It should be noted that when the alkylene group has an -O- or silanine skeleton group, it is preferable that the -O- or silanine skeleton group is present between carbon atoms. Additionally, the alkylene group has a -C(O)N(R) skeleton. d When α-, dialkylmethylenesilyl, or divalent organopolysiloxane is used, it is preferably located between carbon atoms or with (O). u4These groups are located at the end of the bonded side.

[0290] Q b4 The alkylene group represented preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0291] u4 is either 0 or 1.

[0292] As -(O) u4 -Q b4 - From the perspective of easy compound production, the preferred compounds are -CH2CH2-, -CH2CH2CH2-, -CH2OCH2CH2CH2-, -CH2OCH2CH2CH2CH2CH2-, -OCH2CH2CH2-, -OSi(CH3)2CH2CH2CH2-, -OSi(CH3)2OSi(CH3)2CH2CH2CH2-, and -CH2CH2CH2Si(CH3)2PhSi(CH3)2CH2CH2- (wherein the right side is bonded to Si).

[0293] w1 is an integer from 0 to 2, preferably 0 or 1, and especially preferably 0.

[0294] [-(O) u4 -Q b4 -J 1 In the presence of more than two, more than two [-(O)] u4 -Q b4 -J 1 They can be the same or different.

[0295] R 31 When there are two or more, the two or more (-R) 31 They can be the same or different.

[0296] Z 1 The and Q 1 When the terminal side of the bond is an alkylene group, the following groups can be cited as specific examples of the group (3-1A-4). In the following formulas, * indicates a bond with Z. 1 The bonding positions.

[0297]

[0298] Z 1 When the group is an organopolysiloxane, specific examples of the group (3-1A-4) include the following groups. In the following formulas, * indicates a group related to Z. 1 The bonding positions.

[0299]

[0300] In group (3-1A-5), Q a5 It can be an alkylene group that optionally has an ether-like oxygen atom.

[0301] The number of carbon atoms in the alkylene group having an ether-like oxygen atom is preferably 1 to 10, and particularly preferably 2 to 6.

[0302] As Q a5 From the perspective of ease of compound production, -OCH2CH2CH2-, -OCH2CH2OCH2CH2CH2-, -CH2CH2-, and -CH2CH2CH2- (where the right side is bonded to Si) are preferred.

[0303] Q b5 It is an alkylene group, or an organopolysiloxane group with an ether oxygen atom or a divalent oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms.

[0304] Q b5 The alkylene group represented preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0305] By Q b5 The number of carbon atoms in the alkylene group having an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0306] As Q b5 From the perspective of ease of compound preparation, -CH2CH2CH2- and -CH2CH2OCH2CH2CH2- are preferred (wherein, the right side is the same as J). 1 (bonding).

[0307] 3 [-Q] b5 -J 1 They can be the same or different.

[0308] Z 1 The and Q 1 When the terminal side of the bond is an alkylene group, the following groups can be cited as specific examples of groups (3-1A-5). In the following formulas, * indicates a bond with Z. 1 The bonding positions.

[0309]

[0310] Z 1When the group is an organopolysiloxane alkyl group, the following groups can be cited as specific examples of the group (3-1A-5). In the following formula, * indicates a group related to Z. 1 The bonding positions.

[0311]

[0312] Q in group (3-1A-6) e The definition is as defined in the group (3-1A-4) above.

[0313] v is 0 or 1.

[0314] Q a6 It can be an alkylene group that optionally has an ether-like oxygen atom.

[0315] The number of carbon atoms in the alkylene group having an ether-like oxygen atom is preferably 1 to 10, and particularly preferably 2 to 6.

[0316] As Q a6 From the perspective of ease of compound preparation, -CH2OCH2CH2CH2-, -CH2OCH2CH2OCH2CH2CH2-, -CH2CH2-, and -CH2CH2CH2- are preferred (where the right side is the same as Z). a (bonding).

[0317] Z a It is an organopolysiloxane group with a (w2+1) valence, or a (w2+1) valence group having an alkylene group between the organopolysiloxane groups.

[0318] w2 is an integer between 2 and 7.

[0319] Examples of organopolysiloxane groups with a (w2+1) valence and groups with a (w2+1) valence and having an alkylene group between the organopolysiloxane groups include the following groups. Wherein, R in the following formula... a As described above. * indicates the bonding site.

[0320]

[0321] Q b6 It is an alkylene group, or an organopolysiloxane group with an ether oxygen atom or a divalent oxygen atom between carbon atoms of an alkylene group having two or more carbon atoms.

[0322] Q b6 The alkylene group represented preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10.

[0323] By Q b6 The number of carbon atoms in the alkylene group having an etheric oxygen atom or a divalent organopolysiloxane group between carbon atoms is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0324] As Q b6 From the perspective of ease of compound production, -CH2CH2- and -CH2CH2CH2- are preferred.

[0325] w2 of [-Q] b6 -J 1 They can be the same or different.

[0326] Specific examples of the group (3-1A-6) include the following groups. In the following formulas, * indicates a group related to Z. 1 The bonding positions.

[0327]

[0328] In group (3-1A-7), Z c Hydrocarbon groups with a valence of (w3+w4+1).

[0329] w3 is an integer greater than or equal to 4.

[0330] w4 is an integer greater than or equal to 0.

[0331] Q e s4, Q a4 t4, Q b4 The definition and preferred range of u4 are the same as those of the symbols in group (3-1A-4).

[0332] Z c It can be composed of hydrocarbon chains, or it can have ether-like oxygen atoms between carbon atoms in the hydrocarbon chain, preferably composed of hydrocarbon chains.

[0333] Z c The valence is preferably 5 to 20, more preferably 5 to 10, even more preferably 5 to 8, and particularly preferably 5 to 6.

[0334] Z c The number of carbon atoms is preferably 3 to 50, more preferably 4 to 40, and even more preferably 5 to 30.

[0335] w3 is preferably 4~20, more preferably 4~16, even more preferably 4~8, and particularly preferably 4~5.

[0336] w4 is preferably 0~10, more preferably 0~8, further preferably 0~6, particularly preferably 0~3, and most preferably 0~1.

[0337] [-(OQ b4 ) u4 -J 1 In the presence of more than two, more than two [-(OQ] b4 ) u4 -J 1 They can be the same or different.

[0338] Z 1 Q 1 When the terminal molecule is alkylene, the following groups can be cited as specific examples of groups (3-1A-7). In the following formulas, * indicates a group related to Z. 1 The bonding positions.

[0339]

[0340] Z 1 Q 1 When the side terminal is an organopolysiloxane alkyl group, the following groups can be cited as specific examples of the group (3-1A-7). In the following formula, * indicates a group related to Z. 1 The bonding positions.

[0341]

[0342] Q 1 It can be group (g2-1) (where j1=d1+d3, g1=d2+d4), group (g2-2) (where j1=e1, g1=e2), group (g2-3) (where j1=1, g1=2), group (g2-4) (where j1=h1, g1=h2), group (g2-5) (where j1=i1, g1=i2), group (g2-6) (where j1=1, g1=1), or group (g2-7) (where j1=1, g1=i3).

[0343]

[0344] (-A 1 -Q 12 -) e1 C(R e2 ) 4-e1-e2 (-Q 22 -) e2 …(g2-2)

[0345] -A 1 -Q 13 -N(-Q 23 -)2…(g2-3)

[0346] (-A 1 -Q14 -) h1 Z(-Q 24 -) h2 …(g2-4)

[0347] (-A 1 -Q 15 -) i1 Si(R e3 ) 4-i1-i2 (-Q 25 -) i2 …(g2-5)

[0348] -A 1 -Q 26 - …(g2-6)

[0349] -A 1 -Q 12 -CH(-Q 22 -)-Si(R e3 ) 3-i3 (-Q 25 -) i3 …(g2-7)

[0350] In equations (g2-1) to (g2-7), A 1 Side and Z 1 Bonding, Q 22 Q 23 Q 24 Q 25 Or Q 26 Side and J 1 Bonding.

[0351] A 1 For single bond, -C(O)NR e6 -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR e6 -、-O- or SO2NR e6 -

[0352] Z and A 1 When the terminal of the bonded side is an alkylene group, A 1 The terminal end of the side bonded to Z is not an alkylene group. Additionally, when Z is an organopolysiloxane alkyl group, A... 1 The end of the side bonded to Z is not an organopolysiloxane.

[0353] Q 12 It is a single bond, an alkylene group, or an alkylene group having a -C(O)NR bond between carbon atoms. 6 -、-C(O)-、-NR 6 - or O- groups, Q12 When there are two or more, there are two or more Q. 12 They can be the same or different.

[0354] Q 13 For a single bond (where Q is a single bond) 1 For -C(O)-, alkylene groups, and alkylene groups with more than 2 carbon atoms having -C(O)NR between carbon atoms. 6 -、-C(O)-、-NR 6 A group consisting of - or O-, or a group having -C(O)- at the N-side end of an alkylene group.

[0355] Q 14 In Q 14 When the bonded Z atom is a carbon atom, it is Q. 12 In Q 14 When the bonded Z atom is a nitrogen atom, it is Q. 13 In Q 14 In the case of two or more, two or more Q 14 They can be the same or different.

[0356] Q 15 It is an alkylene group, or an alkylene group having -C(O)NR between carbon atoms. 6 -、-C(O)-、-NR 6 - or O- groups, Q 15 When there are two or more, there are two or more Q. 15 They can be the same or different.

[0357] Q 22 Alkylenes, wherein the carbon-carbon atoms of alkylenes having two or more carbon atoms have a -C(O)NR bond. 6 -、-C(O)-、-NR 6 - or O- groups, with -C(O)NR at the end of the alkylene group on the side not connected to Si. 6 -、-C(O)-、-NR 6 - or O- groups, or alkylene groups having -C(O)NR between carbon atoms in carbon-carbon pairs. 6 -、-C(O)-、-NR 6 - or O-, and the end of the side not connected to Si has -C(O)NR 6 -、-C(O)-、-NR 6 - or O- groups, in Q 22 In the case of two or more, two or more Q 22 They can be the same or different.

[0358] Q23 It is an alkylene group, or an alkylene group having a -C(O)NR between carbon atoms in the carbon-carbon interval of two or more carbon atoms. 6 -、-C(O)-、-NR 6 - or O- groups, 2 Q 23 They can be the same or different.

[0359] Q 24 In Q 24 When the bonded Z atom is a carbon atom, it is Q. 22 In Q 24 When the bonded Z atom is a nitrogen atom, it is Q. 23 In Q 24 In the case of two or more, two or more Q 24 They can be the same or different.

[0360] Q 25 It is an alkylene group, or an alkylene group having -C(O)NR between carbon atoms. 6 -、-C(O)-、-NR 6 - or O- groups, Q 25 When there are two or more, there are two or more Q. 25 They can be the same or different.

[0361] Q 26 It is an alkylene group, or an alkylene group having a -C(O)NR between carbon atoms in the carbon-carbon interval of two or more carbon atoms. 6 -、-C(O)-、-NR 6 - or O- groups.

[0362] Q 22 Q 23 Q 24 Q 25 Q 26 When it is an alkylene group, the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6.

[0363] Z is a (h1+h2) valence group with a ring structure, and the group has Q 14 Directly bonded carbon or nitrogen atoms, and possessing Q 24 Directly bonded carbon or nitrogen atoms.

[0364] R e1 It is a hydrogen atom or an alkyl group, having two or more R atoms. e1 At that time, more than 2 R e1 They can be the same or different.

[0365] R e2It can be a hydrogen atom, hydroxyl group, alkyl group or acyloxy group.

[0366] R e3 It is an alkyl group. R 6 It consists of hydrogen atoms and alkyl or phenyl groups having 1 to 6 carbon atoms.

[0367] d1 is an integer from 0 to 3, preferably 1 or 2.

[0368] d2 is an integer from 0 to 3, preferably 1 or 2.

[0369] d1+d2 are integers from 1 to 3.

[0370] d3 is an integer from 0 to 3, preferably 0 or 1.

[0371] d4 is an integer from 0 to 3, preferably 2 or 3.

[0372] d3+d4 is an integer from 1 to 3.

[0373] d1+d3 is an integer from 1 to 5, preferably 1 or 2.

[0374] d2+d4 is an integer from 1 to 5, preferably 4 or 5.

[0375] e1+e2 is 3 or 4.

[0376] e1 is an integer from 1 to 3, preferably 1 or 2.

[0377] e2 is an integer from 1 to 3, preferably 2 or 3.

[0378] h1 is an integer greater than or equal to 1, preferably 1 or 2.

[0379] h2 is an integer greater than or equal to 1, preferably 2 or 3.

[0380] i1+i2 is 3 or 4.

[0381] i1 is an integer from 1 to 3, preferably 1 or 2.

[0382] i2 is an integer from 1 to 3, preferably 2 or 3.

[0383] i3 is 2 or 3.

[0384] Considering the ease of compound manufacturing and the superior wear resistance of the surface treatment layer, Q 12 Q 13 Q 14 Q 15 Q 22 Q 23 Q 24 Q 25 and Q 26The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the number of carbon atoms can be 1 to 10, 1 to 6, or 1 to 4. The lower limit for the number of carbon atoms in the alkylene group when a specific bond exists between carbon atoms is 2.

[0385] As ring structures in Z, the above-mentioned ring structures can be listed, and the preferred method is also the same. It should be noted that, due to Q... 14 Q 24 Directly bonded to the ring structure in Z, therefore, for example, there are no alkylene groups connected to the ring structure, and Q 14 Q 24 The case of further connection with the alkylene group.

[0386] From the perspective of ease of compound production, R e1 R e2 or R e3 The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3, and even more preferably 1 to 2.

[0387] From the perspective of ease of compound production, R e2 The alkyl moiety of the acyloxy group preferably has 1 to 6 carbon atoms, more preferably 1 to 3, and even more preferably 1 to 2.

[0388] Considering the ease of compound manufacturing and the superior wear resistance of the surface treatment layer, h1 is preferably 1 to 6, more preferably 1 to 4, further preferably 1 or 2, and particularly preferably 1.

[0389] As for h2, considering the ease of compound manufacturing and the superior wear resistance of the surface treatment layer, 2 to 6 are preferred, 2 to 4 are more preferred, and 2 or 3 are particularly preferred.

[0390] As Q 1 Other forms can be listed as group (g2-8) (where j1=d1+d3, g1=d2×k3+d4×k3), group (g2-9) (where j1=e1, g1=e2×k3), group (g2-10) (where j1=1, g1=2×k3), group (g2-11) (where j1=h1, g1=h2×k3), group (g2-12) (where j1=i1, g1=i2×k3), group (g2-13) (where j1=1, g1=k3), or group (g2-14) (where j1=1, g1=i3×k3).

[0391]

[0392] (-A1 -Q 12 -) e1 C(R e2 ) 4-e1-e2 (-Q 22 -G 1 ) e2 …(g2-9)

[0393] -A 1 -Q 13 -N(-Q 23 -G 1 )2…(g2-10)

[0394] (-A 1 -Q 14 -) h1 Z(-Q 24 -G 1 ) h2 …(g2-11)

[0395] (-A 1 -Q 15 -) i1 Si(R e3 ) 4-i1-i2 (-Q 25 -G 1 ) i2 …(g2-12)

[0396] -A 1 -Q 26 -G 1 …(g2-13)

[0397] -A 1 -Q 12 -CH(-Q 22 -G 1 )-Si(R e3 ) 3-i3 (-Q 25 -G 1 ) i3 …(g2-14)

[0398] In equations (g2-8) to (g2-14), A 1 Side and Z 1 Bonding, G 1 Side and J 1 Bonding.

[0399] Z and A 1 When the terminal of the bonded side is an alkylene group, Q 1 The terminal end of the side bonded to Z is not an alkylene group. Additionally, when Z is an organopolysiloxane alkyl group, A... 1The end of the side bonded to Z is not an organopolysiloxane.

[0400] G 1 For the following group (g3), Q 1 Having more than 2 Gs 1 They can be the same or different. G 1 The symbols other than those in equations (g2-1) to (g2-7) are the same.

[0401] -Si(R 8 ) 3-k3 (-Q 3 -) k3 …(g3)

[0402] In the group (g3), the Si side is related to Q. 22 Q 23 Q 24 Q 25 and Q 26 Connection, Q 3 Side and J 1 Connection. R 8 It is an alkyl group. Q 3 Alkylenes, wherein the carbon-carbon atoms of alkylenes having two or more carbon atoms have a -C(O)NR bond. 6 -、-C(O)-、-NR 6 - or -O- groups, or (OSi(R) 9 )2) p -O-, 2 or more Qs 3 They can be the same or different. k3 is 2 or 3. R 6 It is an alkyl or phenyl group with 1 to 6 carbon atoms and hydrogen atoms. R 9 It is an alkyl, phenyl, or alkoxy group, with two Rs. 9 They can be the same or different. p is an integer from 0 to 5. When p is 2 or higher, there are two or more (OSi(R)). 9 2) They can be the same or different.

[0403] Considering the ease of compound manufacturing and the superior wear resistance of the surface treatment layer, Q 3 The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 2 to 20. It can be 2 to 10 or 2 to 6. Examples include 2, 3, 8, 9, and 11. Alternatively, the aforementioned number of carbon atoms can be 1 to 10, 1 to 6, or 1 to 4. The lower limit for the number of carbon atoms in the alkylene group when a specific bond exists between carbon atoms is 2.

[0404] From the perspective of ease of compound production, R 8The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3, and even more preferably 1 to 2.

[0405] From the perspective of ease of compound production, R 9 The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3, and even more preferably 1 to 2.

[0406] From the perspective of the excellent storage stability of the compound, R 9 The number of carbon atoms in the alkoxy group is preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1 to 2.

[0407] p is preferably 0 or 1.

[0408] As a compound of this disclosure, the compound represented by the following formula (4) is preferred, for example.

[0409] [(R 111 3Si-OZ 1 ]-Q 1 -(J 1 ) n2 …Formula (4)

[0410] Among them, R 111 Each is independently an alkyl or trialkylsilyloxy group, Q 1 For -O-, Z 1 It is an organopolysiloxane alkyl group. This compound is preferred from the perspectives of ease of industrial manufacture, ease of handling, and superior water repellency and abrasion resistance of the surface treatment layer.

[0411] Examples of compounds disclosed herein include those with the following formula. From the perspectives of ease of industrial manufacture, ease of handling, and superior water repellency and abrasion resistance of the surface treatment layer, compounds with the following formula are preferred. R in the compounds with the following formula... t With [R] in equation (1) 11 -(Q) r1 -Z 1 The same applies, and the preferred selection method is also the same.

[0412] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented as Q in formula (1). 1 Compounds with a group (g2-1) can be exemplified by compounds with the following formula.

[0413]

[0414] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-1) can be exemplified by compounds with the following formula.

[0415]

[0416] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-2) can be exemplified by compounds with the following formula. In the following formula, Ak refers to an alkyl group (e.g., an alkyl group with 1 to 15 carbon atoms).

[0417]

[0418]

[0419] In Z 1 In the case of an organopolysiloxane alkyl group, Q in formula (1) 1 Compounds with the group (g2-2) can be exemplified by compounds of the following formula.

[0420]

[0421]

[0422] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-3) can be exemplified by compounds with the following formula.

[0423]

[0424] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-3) can be exemplified by compounds with the following formula.

[0425]

[0426] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-4) can be exemplified by compounds with the following formula.

[0427]

[0428] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-4) can be exemplified by compounds with the following formula.

[0429]

[0430] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-5) can be exemplified by compounds with the following formula.

[0431]

[0432] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-5) can be exemplified by compounds with the following formula.

[0433]

[0434] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-6) can be exemplified by compounds with the following formula.

[0435]

[0436] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-6) can be exemplified by compounds with the following formula.

[0437]

[0438] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-7) can be exemplified by compounds with the following formula.

[0439]

[0440] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-7) can be exemplified by compounds with the following formula.

[0441]

[0442] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1Compounds with a group (g2-8) can be exemplified by compounds with the following formula.

[0443]

[0444] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-8) can be exemplified by compounds with the following formula.

[0445]

[0446] Q in Equation 1 1 Compounds with a group (g2-9) can be exemplified by compounds with the following formula.

[0447]

[0448] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with a group (g2-10) can be exemplified by compounds with the following formula.

[0449]

[0450] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-10) can be exemplified by compounds with the following formula.

[0451]

[0452] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with the group (g2-11) can be exemplified by compounds with the following formula.

[0453]

[0454] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-11) can be exemplified by compounds with the following formula.

[0455]

[0456] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1Compounds with a group (g2-12) can be exemplified by compounds with the following formula.

[0457]

[0458] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-12) can be exemplified by compounds with the following formula.

[0459]

[0460] Z 1 The and Q 1 When the terminal of the bonded side is an alkylene group, it is represented by Q in Formula 1. 1 Compounds with the group (g2-13) can be exemplified by compounds with the following formula.

[0461]

[0462] In Z 1 In the case of an organopolysiloxane alkyl group, Q in Formula 1 1 Compounds with a group (g2-13) can be exemplified by compounds with the following formula.

[0463]

[0464] Q in Equation 1 1 Compounds with a group (g2-14) can be exemplified by compounds with the following formula.

[0465]

[0466] Specific examples of compounds disclosed herein include the following compounds, but the scope is not limited to these compounds. It should be noted that n in the formula is an average value, which can be 1 or more, preferably a number from 2 to 500, more preferably a number from 3 to 300. Examples include 6, 13, 17, and 18. β in the formula is an integer representing the number of methylene groups, preferably 1 to 30, more preferably 1 to 20, further preferably 4 to 20, and particularly preferably 5 to 15. Examples include 10, 11, 15, and 21. R is an alkylene group, preferably with 1 to 6 carbon atoms, more preferably 1 to 3, and further preferably 1 to 2.

[0467]

[0468]

[0469]

[0470] The number-average molecular weight (Mn) of the compounds disclosed herein is preferably 500 to 20,000, more preferably 600 to 18,000, and even more preferably 700 to 15,000.

[0471] If Mn is above 500, the surface treatment layer exhibits superior wear resistance. If Mn is below 20,000, the viscosity is easily adjusted to an appropriate range, and the solubility is improved, resulting in excellent operability during film formation.

[0472] [Methods for manufacturing compounds]

[0473] The method for manufacturing the above-mentioned compound is not particularly limited. For example, by using a known method, the equivalent of [R] in formula (1) can be obtained. 11 -(Q) r1 -Z 1 ] p1 -Q 11 This compound is obtained by introducing a P group into an organopolysiloxane. Here, Q 11 It replaces Q 1 The two carbon atoms at the end are designated as C=C groups, and H-[Si(R) is used as an intermediate in the introduction of group P. 1 )2-X] n1 -Si(R 1 3. H-[Si(R) as an intermediate 1 )2-X] n1 -Si(R 1 Details of 3 will be described later. Additionally, the reaction conditions can be adjusted appropriately based on the examples described later.

[0474] In addition, as other examples of methods for manufacturing this compound, one can cite methods equivalent to [R] 11 -(Q) r1 -Z 1 ] p1 -Si(R 8 )2-H organopolysiloxane alkyl group with R 1 -[Si(R 1 )2-X] n1 -Si(R 1 3. The method of reaction. Here, R 8 R in the above group (A6) 8 The same. Specifically, the following is a reaction of a hydrogen-terminated organopolysiloxane as shown below with hexamethoxydisiloxane ((CH3O)3Si-O-Si(OCH3)3).

[0475]

[0476] [Composition]

[0477] The compositions disclosed herein only require that they contain the compounds disclosed herein, and there are no particular limitations on other components besides the compounds disclosed herein. The compositions disclosed herein preferably contain the compounds disclosed herein and a liquid medium. When a liquid medium is included, the compositions disclosed herein need only be liquids, and can be solutions or dispersions.

[0478] The compositions disclosed herein may contain at least one of the compounds shown in formula (1) and formula (2). It should be noted that the surface treatment agents disclosed herein may contain both the compounds shown in formula (1) and formula (2).

[0479] The compositions disclosed herein may contain only the compounds disclosed herein, or they may contain byproducts or other impurities generated during the manufacturing process of the compounds disclosed herein.

[0480] The content of the compound disclosed herein is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass, relative to the total amount of the composition disclosed herein. In the case of the composition disclosed herein used in a wet coating method, the content of the compound disclosed herein may be 0.01 to 10% by mass, 0.02 to 5% by mass, 0.03 to 3% by mass, or 0.05 to 2% by mass, relative to the total amount of the composition disclosed herein.

[0481] The liquid medium contained in the composition disclosed herein may be only one type or may be two or more types.

[0482] Organic solvents are preferred as liquid media.

[0483] As organic solvents, examples include compounds composed only of hydrogen and carbon atoms, as well as compounds composed only of hydrogen, carbon, and oxygen atoms. Specifically, examples include hydrocarbon organic solvents, ketone organic solvents, ether organic solvents, ester organic solvents, glycol organic solvents, and alcohol organic solvents.

[0484] Specific examples of hydrocarbon-based organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, dicyclohexane, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.

[0485] Specific examples of ketone-based organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 4-heptanone, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, and isophorone.

[0486] Specific examples of ether-based organic solvents include diethyl ether, cyclopentylmethyl ether, tetrahydrofuran, and 1,4-dioxane.

[0487] Specific examples of ester-based organic solvents include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, amyl acetate, isoamyl acetate, ethyl 3-ethoxypropionate, ethyl lactate, ethylene glycol monobutyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, propylene glycol monomethyl acetate, propylene glycol dimethyl acetate, and ethylene glycol monoethyl ether acetate. 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 monobutyl ether acetate, propylene glycol monopropyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butanediol diacetate, 1,4-butanediol diacetate, 1,3-butanediol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.

[0488] Specific examples of diol-based organic solvents include ethylene glycol, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, tetraethylene glycol monobutyl ether, ethylene glycol monohexyl ether, diethylene glycol monohexyl ether, ethylene glycol mono-2-ethylhexyl ether, diethylene glycol mono-2-ethylhexyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monotert-butyl ether, ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ... Butyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-butanediol, propylene glycol n-propyl ether, propylene glycol n-butyl ether, diethylene glycol monoethyl ether, dipropylene glycol n-propyl ether, dipropylene 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, polyethylene glycol dimethyl ether.

[0489] Specific examples of alcohol-based organic solvents include methanol, ethanol, 1-propanol, isopropanol, n-butanol, diacetone alcohol, isobutanol, sec-butanol, tert-butanol, pentanol, 3-methyl-1,3-butanediol, 1,3-butanediol, 1,3-butylene diol, 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, isothiazol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol, 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol.

[0490] In addition, examples of organic solvents include halogenated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, siloxane compounds, and fluorinated organic solvents.

[0491] Specific examples of halogenated organic solvents include dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, m-dichlorobenzene, and 1,2,3-trichloropropane.

[0492] Examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolone.

[0493] Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0494] Examples of siloxane compounds include hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, and decamethyltetrasiloxane.

[0495] Examples of fluorinated organic solvents include polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C6F...). 13CH2CH3 (e.g., ASAHIKLIN AC-6000 manufactured by AGC Corporation), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., ZEORORA H manufactured by ZEON Corporation, Japan); hydrofluoroethers (HFE) (e.g., perfluoropropyl methyl ether (C3F7OCH3) (e.g., Novec 7000 manufactured by Sumitomo 3M Corporation), perfluorobutyl methyl ether (C4F9OCH3) (e.g., Novec 7100 manufactured by Sumitomo 3M Corporation), perfluorobutyl ethyl ether (C4F9OC2H5) (e.g., manufactured by Sumitomo 3M Corporation) Novec (trademark) 7200), perfluorohexyl methyl ether (C2F5CF(OCH3)C3F7) (e.g. Novec (trademark) 7300 manufactured by Sumitomo 3M) and other alkyl perfluoroalkyl ethers (perfluoroalkyl and alkyl can be straight-chain or branched), as well as CF3CH2OCF2CHF2 (e.g. ASAHIKLIN (registered trademark) AE-3000 manufactured by AGC)); hydrofluoroolefins (HFO) (e.g. 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (e.g. Amorea (registered trademark) AS-300 manufactured by AGC)).

[0496] The content of the liquid medium relative to the total amount of the composition disclosed herein is preferably 60 to 99.999% by mass, more preferably 80 to 99.99% by mass, and even more preferably 90 to 99.9% by mass. In the case of the composition disclosed herein used in a wet coating method, the content of the liquid medium relative to the total amount of the composition disclosed herein can be 90 to 99.99% by mass, 95 to 99.98% by mass, 97 to 99.97% by mass, or 98 to 99.95% by mass.

[0497] In addition to the compounds and liquid media disclosed herein, the compositions may also contain other components without impairing the effects of the disclosure.

[0498] Other components include, for example, known additives such as acid catalysts and basic catalysts that promote the hydrolysis and condensation of group P.

[0499] As catalysts, any suitable acid or base, transition metal (e.g., Ti, Ni, Sn, Zr, Al, B, etc.), sulfur-containing compounds with lone pairs of electrons in their molecular structure, nitrogen-containing compounds (e.g., sulfoxide compounds, aliphatic amine compounds, aromatic amine compounds, phosphoramide compounds, amide compounds, urea compounds, etc.) can be used.

[0500] Examples of acid catalysts include acetic acid, formic acid, trifluoroacetic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, sulfonic acid, methanesulfonic acid, and p-toluenesulfonic acid.

[0501] In addition, examples of alkaline catalysts include ammonia, sodium hydroxide, potassium hydroxide, and organic amines such as triethylamine and diethylamine.

[0502] In addition, other components may include metal compounds having hydrolyzable groups (hereinafter, metal compounds having hydrolyzable groups will also be referred to as "specific metal compounds"). If the composition disclosed herein contains specific metal compounds, the slip properties and antifouling properties of the surface treatment layer can be further improved. Examples of specific metal compounds include the following formulas (M1) to (M3).

[0503] M(X) b1 ) m1 (X) b2 ) m2 (X) b3 ) m3 …(M1)

[0504] Si(X) b4 (X) b5 3… (M2)

[0505] (X) b6 )3Si-(Y b1 )-Si(X b7 )3…(M3)

[0506] In formula (M1),

[0507] M represents a trivalent or tetravalent metal atom.

[0508] X b1 Each of them independently represents a hydrolyzable group.

[0509] X b2 Each group independently represents a group containing a siloxane skeleton.

[0510] X b3 Each can be used independently to represent a hydrocarbon chain group.

[0511] m1 is an integer between 2 and 4.

[0512] m2 and m3 are each independent integers from 0 to 2.

[0513] When M is a trivalent metal atom, m1+m2+m3 equals 3; when M is a tetravalent metal atom, m1+m2+m3 equals 4.

[0514] In formula (M2),

[0515] X b4 This indicates a hydrolyzable silane oligomer group.

[0516] Xb5 Each is independently a hydrolyzable group or an alkyl group having 1 to 4 carbon atoms.

[0517] In formula (M3),

[0518] X b6 and X b7 Each is independently a hydrolyzable group or a hydroxyl group.

[0519] Y b1 This indicates a divalent organic group.

[0520] In formula (M1), the metal represented by M also includes half-metals such as Si and Ge. Preferably, M is a trivalent or tetravalent metal, more preferably Al, Fe, In, Hf, Si, Ti, Sn, and Zr, further preferably Al, Si, Ti, or Zr, and particularly preferably Si.

[0521] In equation (M1), X is... b1 The hydrolyzable groups shown can be exemplified by R in group P. 1 The hydrolyzable groups shown are the same groups.

[0522] X b2 The shown group containing a siloxane backbone has a siloxane unit (-Si-O-), which can be linear or branched. As the siloxane unit, dialkylsiloxy is preferred, and examples include dimethylsiloxy and diethylsiloxy. The number of repeating units of the siloxane unit in the group containing the siloxane backbone is 1 or more, preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3.

[0523] Groups containing a siloxane skeleton may include a divalent hydrocarbon group in a portion of the siloxane skeleton. Specifically, a portion of the oxygen atoms in the siloxane skeleton may be replaced by a divalent hydrocarbon group. Examples of such divalent hydrocarbon groups include alkylene groups such as methylene, ethylene, propylene, and butylene.

[0524] The silicon atoms at the ends of the groups containing the siloxane skeleton may be bonded with hydrolyzable groups, groups with hydrolyzable groups, hydrocarbon groups (preferably alkyl groups), etc.

[0525] The number of elements containing groups with a siloxane skeleton is preferably 100 or less, more preferably 50 or less, and even more preferably 30 or less. The aforementioned number of elements is preferably 10 or more.

[0526] As a group containing a siloxane backbone, preferably * -(O-Si(CH3)2) n The group shown in CH3, where n is an integer from 1 to 5, and * indicates the bonding site with an adjacent atom.

[0527] Xb3 The hydrocarbon chain-containing group shown can be a group consisting solely of a hydrocarbon chain, or a group having ether-like oxygen atoms between carbon atoms in the hydrocarbon chain. The hydrocarbon chain can be straight-chain or branched, preferably straight-chain. The hydrocarbon chain can be saturated or unsaturated, preferably saturated. 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. As the hydrocarbon chain-containing group, alkyl is preferred, more preferably methyl, ethyl, or propyl.

[0528] m1 is preferably 3 or 4.

[0529] As the compound represented by formula (M1), compounds represented by formulas (M1-1) to (M1-5) with M being Si are preferred, and compounds represented by formula (M1-1) are more preferred. As the compound represented by formula (M1-1), tetraethoxysilane, tetramethoxysilane, and triethoxymethylsilane are preferred.

[0530] Si(X) b1 4…(M1-1)

[0531] CH3-Si(X) b1 3…(M1-2)

[0532] C2H5-Si(X) b1 3…(M1-3)

[0533] n-C3H7-Si(X) b1 3…(M1-4)

[0534] (CH3)2CH-Si(X) b1 3… (M1-5)

[0535] In formula (M2), X b4 The number of silicon atoms contained in the hydrolyzable silane oligomer group shown is preferably 3 or more, more preferably 5 or more, and even more preferably 7 or more. The aforementioned number of silicon atoms is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less.

[0536] The hydrolyzable silane oligomer group optionally has an alkoxy group bonded to a silicon atom. Examples of such alkoxy groups include methoxy, ethoxy, propoxy, and butoxy, with methoxy and ethoxy being preferred. The hydrolyzable silane oligomer group may have one or more of these alkoxy groups, with one being preferred.

[0537] Examples of hydrolyzable silane oligomer groups include (C2H5O)3Si-(OSi(OC2H5)2)4O- * And so on. Here, * indicates the bonding site with an adjacent atom.

[0538] In equation (M2), X is... b5 The hydrolyzable groups shown can be listed as those related to R in group P. 1 The hydrolyzable groups shown are the same as those for cyano, hydrogen, and allyl groups, preferably alkoxy or isocyanate groups. As an alkoxy group, an alkoxy group with 1 to 4 carbon atoms is preferred.

[0539] As X b5 Preferably, hydrolyzable groups are used.

[0540] Examples of compounds represented by formula (M2) include (H5C2O)3-Si-(OSi(OC2H5)2)4OC2H5, etc.

[0541] The compound represented by formula (M3) is a compound with reactive silyl groups at both ends of a divalent organic group, i.e., a bissilane.

[0542] In formula (M3), X is used as b6 and X b7 The hydrolyzable groups shown may include alkoxy, acyloxy, ketoxime, alkenyloxy, amino, aminooxy, amide, isocyanate, and halogen atoms, with alkoxy and isocyanate groups being preferred. As an alkoxy group, an alkoxy group with 1 to 4 carbon atoms is preferred, and methoxy or ethoxy is more preferred.

[0543] In formula (M3), X b6 and X b7 They can be the same groups or different groups. From the point of view of easy access, X b6 and X b7 Preferably, the groups are the same as each other.

[0544] In formula (M3), Y b1 The divalent organic group is a reactive silyl group connected to both ends. The Y-shaped divalent organic group... b1 The number of carbon atoms is preferably 1 to 8, more preferably 1 to 3.

[0545] As Y b1 Examples include alkylene, phenylene, and alkylene with an ether-like oxygen atom between the carbon atoms. Examples include -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2CH2-, -CH2C(CH3)2CH2-, -C(CH3)2CH2CH2C(CH3)2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH(CH3)CH2OCH2CH(CH3)-, and -C6H4-.

[0546] Examples of compounds represented by formula (M3) include (CH3O)3Si(CH2)2Si(OCH3)3, (C2H5O)3Si(CH2)2Si(OC2H5)3, (OCN)3Si(CH2)2Si(NCO)3, Cl3Si(CH2)2SiCl3, (CH3O)3Si(CH2)6Si(OCH3)3, and (C2H5O)3Si(CH2)6Si(OC2H5)3.

[0547] The content of other components that may be included in the compositions of this disclosure is preferably 10% by mass or less, more preferably 1% by mass or less, relative to the total amount of the compositions of this disclosure. When the compositions of this disclosure contain a specific metal compound, the content of the specific metal compound is preferably 0.01 to 30% by mass, more preferably 0.01 to 10% by mass, and even more preferably 0.05 to 5% by mass, relative to the total amount of the compositions of this disclosure.

[0548] The total content of the compounds of this disclosure and other components (hereinafter also referred to as "solid content concentration") relative to the total amount of the compositions disclosed herein is preferably 0.001 to 40% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass. The solid content concentration of the compositions disclosed herein is a value calculated from the mass of the compositions before heating and the mass after heating in a convection dryer at 120°C for 4 hours.

[0549] The compositions disclosed herein contain a liquid medium, and are therefore useful for coating applications and can be used as coating liquids.

[0550] Other components may include compounds represented by formula (5).

[0551] [Y 1 3Y 2 -(O) v1 -Y 3 ] v2 Y 4 (Si(Y) 5 ) v3 (Y) 6 ) 3-v3 ) v4 …(5)

[0552] In equation (5), Y 2 It is Si, Sn or Ge,

[0553] Y 1 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0554] v1 is either 0 or 1.

[0555] Y3 Each is independently an alkylene chain or a polyepoxide chain, or a combination of an alkylene chain and divalent polysiloxane residues.

[0556] Y 4 It is a linking group with a single bond or a (v2+v4) valence.

[0557] Y 5 Each is an independent hydrocarbon group.

[0558] Y 6 Each is independently a hydrolyzable group or a hydroxyl group.

[0559] v3 is an integer from 0 to 2, each of which is independent.

[0560] v2 and v4 are each an integer greater than or equal to 1.

[0561] Y is preferred as it may optionally contain ether-like oxygen atoms between carbon-carbon atoms. 3 Compounds with alkylene chains or polyepoxide chains.

[0562] Specific examples of compound (5) include the following compounds. γ in the formula is preferably 9 to 50, more preferably 11 to 30, and particularly preferably 11 to 25.

[0563]

[0564] When the other component in this surface treatment agent is compound (5), the content of compound (5) is preferably 50% by mass or less, more preferably 40% by mass or less.

[0565] [Surface treatment agent]

[0566] In one embodiment, the surface treatment agent of this disclosure comprises the compound of this disclosure. Alternatively, the surface treatment agent of this disclosure may comprise the compound of this disclosure and a liquid medium. The surface treatment agent of this disclosure may be a composition of this disclosure. The preferred manner in which the liquid medium is included in the surface treatment agent is the same as the preferred manner in which the liquid medium is included in the composition of this disclosure.

[0567] The compounds disclosed herein contain alkyl groups having two or more carbon atoms, organopolysiloxane alkyl groups, and the P group. Therefore, by using a surface treatment agent containing the compounds disclosed herein, a surface treatment layer with excellent water repellency and abrasion resistance can be formed.

[0568] The surface treatment agent disclosed herein may contain at least one of the compounds shown in formula (1) and formula (2). It should be noted that the surface treatment agent disclosed herein may contain both the compound shown in formula (1) and the compound shown in formula (2).

[0569] The surface treatment agents disclosed herein are particularly preferred for use in optical components.

[0570] [thing]

[0571] In one embodiment, the articles of this disclosure include a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent of this disclosure.

[0572] The surface treatment layer can be formed on a portion of the surface of the substrate or on the entire surface of the substrate. The surface treatment layer can be spread in a film-like manner on the surface of the substrate or distributed in a dotted manner.

[0573] In the surface treatment layer, the compounds of this disclosure are contained in a state in which part or all of the group P has been hydrolyzed and the silanol group has undergone a dehydration condensation reaction.

[0574] The thickness of the surface treatment layer is preferably 1~100 nm, more preferably 1~50 nm. If the thickness of the surface treatment layer is 1 nm or more, the effect based on the surface treatment can be easily and fully obtained. If the thickness of the surface treatment layer is less than 100 nm, the utilization efficiency is high. The thickness of the surface treatment layer can be calculated by using an X-ray diffractometer for thin film analysis (product name "ATX-G", manufactured by RIGAKU) to obtain the interference pattern of reflected X-rays by the X-ray reflectivity method, and then calculating the thickness from the vibration period of the interference pattern.

[0575] There are no particular limitations on the type of substrate, but substrates that are required to be water-repellent can be listed. Examples of substrates include those that are sometimes used in contact with other objects (such as styluses) or human fingers; substrates that are sometimes held by human fingers during operation; and substrates that are placed on other objects (such as platforms).

[0576] Materials that can be used as substrates include metals, resins, glass, sapphire, ceramics, semiconductors, stone, fibers, nonwovens, paper, wood, fur, natural leather, artificial leather, ceramics, and their composites. Glass can also be chemically strengthened.

[0577] Examples of substrates include building materials, decorative building materials, interior decoration products, transportation equipment (e.g., automobiles), billboards, notice boards, water dispensers, tableware, sinks, decorative items (e.g., picture frames, boxes), laboratory equipment, furniture, textile products, and packaging containers; glass or resin used in art, sports, and games; and glass or resin used in the exterior parts (excluding the display) of mobile phones (e.g., smartphones), portable information terminals, game consoles, and remote controls. The substrate can be in the form of a sheet or a film.

[0578] As a substrate, preferred materials include substrates for touch panels, substrates for displays, and eyeglass lenses, with substrates for touch panels being particularly preferred. The preferred material for a substrate for a touch panel is glass or transparent resin.

[0579] The substrate can be a substrate with surface treatments such as corona discharge treatment, plasma treatment, or plasma graft polymerization treatment applied to one or both surfaces. Surface-treated substrates exhibit better adhesion to the surface-treated layer, and the wear resistance of the surface-treated layer is further improved. Therefore, it is preferable to perform surface treatment on the surface of the substrate that contacts the surface-treated layer. Furthermore, when a base layer (described later) is provided, the surface-treated substrate exhibits better adhesion to the base layer, and the wear resistance of the surface-treated layer is further improved. Therefore, when a base layer is provided, it is preferable to perform surface treatment on the surface of the substrate that contacts the base layer.

[0580] The surface treatment layer can be directly applied to the surface of the substrate, or a base layer can be disposed between the substrate and the surface treatment layer. From the viewpoint of further improving the water repellency and abrasion resistance of the surface treatment layer, the articles of this disclosure preferably include a substrate, a base layer disposed on the substrate, and a surface treatment layer disposed on the base layer that has been surface-treated with the surface treatment agent of this disclosure.

[0581] The substrate layer is preferably a layer comprising an oxide containing: silicon; and at least one specific element selected from the group consisting of elements from Group I, Group II, Group IV, Group V, Group XIII and Group XV of the periodic table.

[0582] The elements in Group 1 of the periodic table (hereinafter also referred to as "Group 1 elements") are lithium, sodium, potassium, rubidium, and cesium. From the viewpoint of enabling the formation of a surface treatment layer on the substrate layer without defects and with greater uniformity, or from the viewpoint of further suppressing compositional deviations in the substrate layer between samples, lithium, sodium, and potassium are preferred as Group 1 elements, and sodium and potassium are more preferred. The substrate layer may contain two or more Group 1 elements.

[0583] The elements in Group 2 of the periodic table (hereinafter also referred to as "Group 2 elements") are beryllium, magnesium, calcium, strontium, and barium. From the viewpoint of enabling the formation of a surface treatment layer on the substrate layer without defects and with greater uniformity, or from the viewpoint of further suppressing compositional deviations in the substrate layer between samples, magnesium, calcium, and barium are preferred as Group 2 elements, and magnesium and calcium are more preferred. The substrate layer may contain two or more Group 2 elements.

[0584] The elements in Group 4 of the periodic table (hereinafter also referred to as "Group 4 elements") refer to titanium, zirconium, and hafnium. From the viewpoint of enabling the formation of a surface treatment layer on the substrate layer without defects and with greater uniformity, or from the viewpoint of further suppressing compositional deviations in the substrate layer between samples, titanium and zirconium are preferred as Group 4 elements, with titanium being more preferred. The substrate layer may contain two or more Group 4 elements.

[0585] The elements in Group 5 of the periodic table (hereinafter also referred to as "Group 5 elements") are vanadium, niobium, and tantalum. Vanadium is particularly preferred as a Group 5 element from the viewpoint of superior wear resistance in surface treatment layers. Two or more Group 5 elements may be included in the base layer.

[0586] The elements in Group 13 of the periodic table (hereinafter also referred to as "Group 13 elements") are boron, aluminum, gallium, and indium. From the viewpoint of enabling the formation of a surface treatment layer on the substrate layer without defects and with greater uniformity, or from the viewpoint of further suppressing compositional deviations in the substrate layer between samples, boron, aluminum, and gallium are preferred as Group 13 elements, with boron and aluminum being more preferred. The substrate layer may contain two or more Group 13 elements.

[0587] The elements in Group 15 of the periodic table (hereinafter also referred to as "Group 15 elements") are nitrogen, phosphorus, arsenic, antimony, and bismuth. From the viewpoint of enabling the formation of a surface treatment layer on the substrate layer without defects and with greater uniformity, or from the viewpoint of further suppressing compositional deviations in the substrate layer between samples, phosphorus, antimony, and bismuth are preferred as Group 15 elements, and phosphorus and bismuth are more preferred. The substrate layer may contain two or more Group 15 elements.

[0588] As specific elements included in the base layer, elements from Group 1, Group 2, and Group 13 are preferred due to the superior wear resistance of the surface treatment layer, with elements from Group 1 and Group 2 being more preferred, and elements from Group 1 being even more preferred.

[0589] As a specific element, it can contain only one type of element or two or more types of elements.

[0590] The oxide contained in the substrate layer can be a mixture of individual oxides of the aforementioned elements (silicon and specific elements) (e.g., a mixture of silicon oxide and oxides of specific elements), a composite oxide containing two or more of the aforementioned elements, or a mixture of individual oxides of the aforementioned elements and composite oxides.

[0591] From the viewpoint of having better wear resistance of the surface treatment layer, the ratio of the total molar concentration of the specific element in the substrate layer to the molar concentration of silicon in the substrate layer (specific element / silicon) is preferably 0.02 to 2.90, more preferably 0.10 to 2.00, and even more preferably 0.20 to 1.80.

[0592] The molar concentration (mol%) of each element in the substrate can be determined, for example, by depth-direction analysis based on X-ray photoelectron spectroscopy (XPS) using ion sputtering.

[0593] The substrate layer can be a single layer or multiple layers. The substrate layer can have uneven surfaces.

[0594] The thickness of the substrate layer is preferably 1~100 nm, more preferably 1~50 nm, and even more preferably 2~20 nm. If the thickness of the substrate layer is above the lower limit mentioned above, the adhesion of the surface treatment layer based on the substrate layer is further improved, and the wear resistance of the surface treatment layer is more excellent. If the thickness of the substrate layer is below the upper limit mentioned above, the wear resistance of the substrate layer itself is excellent.

[0595] The thickness of the basal layer was determined by cross-sectional observation of the basal layer based on transmission electron microscopy (TEM).

[0596] The substrate layer can be formed, for example, by vapor deposition or wet coating using vapor deposition materials.

[0597] The vapor deposition material used in the vapor deposition process preferably contains oxides containing silicon and specific elements.

[0598] Specific examples of vapor deposition materials include powder, melt, sintered body, granulated body, and broken body. From an operational point of view, melt, sintered body, and granulated body are preferred.

[0599] Here, "molten body" refers to a solid obtained by melting the powder of vapor-deposited material at a high temperature and then cooling and solidifying it. "Sintered body" refers to a solid obtained by sintering the powder of vapor-deposited material. Alternatively, the powder can be pressed into a molded body to replace the powder of vapor-deposited material. "Granulated body" refers to a solid obtained by mixing the powder of vapor-deposited material with a liquid medium (such as water or organic solvent) to obtain granules, and then drying the granules.

[0600] Vaporized materials can be manufactured, for example, by the following methods.

[0601] • A method of mixing silicon oxide powder with powder of oxides of specific elements to obtain powder of vapor deposition material.

[0602] • A method for obtaining granules by mixing the powder of the above-mentioned vapor deposition material with water, and then drying the granules to obtain granulated vapor deposition material.

[0603] • A method of obtaining a sintered body by drying a mixture of silicon-containing powder (e.g., powder composed of silicon oxide, silica sand, silica gel), powder containing a specific element (e.g., powder of oxide of a specific element, carbonate, sulfate, nitrate, oxalate, hydroxide), and water, and then firing the dried mixture or a molded body formed by pressing it.

[0604] • A method of obtaining a melt by melting silicon-containing powder (e.g., powder composed of silicon oxide, silica sand, silica gel) and powder containing specific elements (e.g., powder of oxides of specific elements, carbonates, sulfates, nitrates, oxalates, hydroxides) at high temperature and then cooling and solidifying the melt.

[0605] As a specific example of a vapor deposition method using vapor deposition materials, vacuum vapor deposition can be cited. Vacuum vapor deposition is a method in which the vapor deposition material evaporates in a vacuum tank and adheres to the surface of a substrate.

[0606] The temperature during vapor deposition (for example, the temperature of the vessel for preparing the vapor deposition material when using a vacuum vapor deposition apparatus) is preferably 100 to 3,000°C, and more preferably 500 to 3,000°C.

[0607] The pressure during vapor deposition (for example, the pressure inside the tank for preparing the vapor deposition material when using a vacuum vapor deposition apparatus) is preferably 1 Pa or less, and more preferably 0.1 Pa or less.

[0608] When using vapor deposition materials to form the base layer, one type of vapor deposition material can be used, or two or more vapor deposition materials containing different elements can be used.

[0609] Specific examples of evaporation methods for vapor-deposited materials include: the resistance heating method, in which the vapor-deposited material is melted and evaporated on a boat made of a high-melting-point metal; and the electron gun method, in which an electron beam is irradiated onto the vapor-deposited material to directly heat the material and melt and evaporate its surface. From the viewpoint that localized heating is possible, allowing even high-melting-point substances to evaporate, and that areas not irradiated by the electron beam are at low temperatures, thus eliminating concerns about reaction with the container or contamination by impurities, the electron gun method is preferred as an evaporation method for vapor-deposited materials.

[0610] Evaporation methods for depositing materials can utilize multiple boats or a single boat containing all the depositing material. Deposition methods can include co-deposition and alternating deposition. Specifically, examples include: mixing silicon dioxide and a specific source in the same boat; co-deposition of silicon dioxide and a specific element source in their respective boats; and alternating deposition in their respective boats. The deposition conditions and sequence are appropriately selected based on the composition of the substrate.

[0611] In wet coating methods, it is preferable to form a base layer on a substrate using a wet coating liquid comprising: a silicon-containing compound, a compound containing a specific element, and a liquid medium.

[0612] Specific examples of silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partial hydrolysis condensates of alkoxysilanes.

[0613] Specific examples of compounds containing a particular element include oxides of a particular element, alkoxides of a particular element, carbonates of a particular element, sulfates of a particular element, nitrates of a particular element, oxalates of a particular element, and hydroxides of a particular element.

[0614] Examples of liquid media that are the same as those included in the compositions disclosed herein can be listed as liquid media.

[0615] The content of the liquid medium is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, relative to the total amount of coating liquid used in the formation of the substrate layer.

[0616] Specific examples of wet coating methods used to form a substrate include spin coating, wiping coating, spray coating, scraper coating, dip coating, mold coating, inkjet coating, flow coating, roller coating, tape casting, Langmuir-Blodgett method, and gravure coating.

[0617] Preferably, the coating liquid is applied wet and then the coating film is dried. The drying temperature of the coating film is preferably 20~200°C, more preferably 80~160°C.

[0618] The items disclosed herein can be optical materials having a surface-treated layer on the outermost layer.

[0619] As optical materials, in addition to optical materials related to displays, a wide variety of optical materials can be preferred.

[0620] As optical materials, examples include cathode ray tubes (CRTs; for example, personal computer monitors), liquid crystal displays, plasma displays, organic EL displays, inorganic thin-film EL dot matrix displays, rear projection displays, fluorescent tubes (VFDs), field emission displays (FEDs), and other displays or protective plates for these displays, or materials on which anti-reflective coatings have been applied to their surfaces.

[0621] The items disclosed herein are preferably optical components. Examples of optical components include car navigation systems, mobile phones, smartphones, digital cameras, digital camcorders, PDAs, portable audio players, car stereos, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, endoscopes and other medical instruments, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films, and anti-reflective films.

[0622] In addition, as optical components, examples include the front surface protection plate, anti-reflective plate, polarizing plate, and anti-glare plate of displays such as PDP and LCD; the disc surface of Blu-ray (registered trademark) discs, DVD discs, CD-R, MO and other optical discs; optical fibers; and the display surface of clocks and watches.

[0623] In particular, the items disclosed herein are preferably displays or touch panels.

[0624] The items disclosed herein can also be medical devices or medical materials. Additionally, the items disclosed herein can also be automotive interior and exterior components. Examples of exterior materials include windows, lamp covers, and exterior camera covers. Examples of interior materials include dashboard covers, navigation system touch panels, and decorative interior materials.

[0625] When the disclosed article is an optical component, the material constituting the surface of the substrate is a material used for optical components, such as glass or transparent plastic. Furthermore, when the disclosed article is an optical component, functional layers such as a hard coating or an anti-reflective layer can be formed on the surface (outermost layer) of the substrate. The anti-reflective layer can be either a single-layer anti-reflective layer or a multi-layer anti-reflective layer.

[0626] Examples of inorganic materials that can be used in antireflective layers include SiO2, SiO, ZrO2, TiO2, TiO, Ti2O3, Ti2O5, Al2O3, Ta2O5, Ta3O5, Nb2O5, HfO2, Si3N4, CeO2, MgO, Y2O3, SnO2, MgF2, and WO3. These inorganic materials can be used alone or in combination of two or more (e.g., as a mixture). In the case of forming a multilayer antireflective layer, it is preferable to use SiO2 and / or SiO as the outermost layer. In the case of an optical glass component for a touch panel, a transparent electrode, such as a thin film using indium tin oxide (ITO) or indium zinc oxide, can be provided on a portion of the surface of the substrate (glass). In addition, the substrate may also have insulating layers, adhesive layers, protective layers, decorative frame layers (I-CON), atomizing film layers, hard coating layers, polarizing films, phase difference films, and liquid crystal display modules, depending on its specific specifications.

[0627] [Item crafting method]

[0628] The method for manufacturing the article disclosed herein is, for example, as follows: a substrate is surface-treated using the surface treatment agent disclosed herein, thereby manufacturing an article on which a surface-treated layer is formed. Examples of surface treatments include dry coating and wet coating.

[0629] Examples of dry coating methods include vacuum evaporation, CVD, and sputtering. From the viewpoints of suppressing compound decomposition and the simplicity of the apparatus, vacuum evaporation is preferred as a dry coating method. During vacuum evaporation, granular materials containing the disclosed compound impregnated in porous metals such as iron or steel can be used. Alternatively, a granular material containing the disclosed compound can be impregnated in porous metals such as iron or steel by impregnating a composition comprising the disclosed compound and a liquid medium, followed by drying the liquid medium.

[0630] Examples of wet coating methods include spin coating, wiping coating, spray coating, scraper coating, dip coating, mold coating, inkjet coating, flow coating, roller coating, tape casting, Langmuir-Blodgett coating, and gravure coating.

[0631] To improve the wear resistance of the surface treatment layer, operations can be performed as needed to promote the reaction between the disclosed compound and the substrate. Examples of such operations include heating, humidification, and light irradiation.

[0632] For example, heating a substrate with a surface treatment layer in a humid atmosphere can promote the hydrolysis of hydrolytic groups, the reaction of hydroxyl groups on the substrate surface with silanol groups, and the formation of siloxane bonds based on the condensation reaction of silanol groups.

[0633] After surface treatment, compounds in the surface treatment layer that are not chemically bonded to other compounds or the substrate can be removed as needed. Examples of removal methods include pouring solvent onto the surface treatment layer or wiping with a cloth soaked in solvent.

[0634] [Intermediate]

[0635] The intermediate of this disclosure is represented by the following formula (3).

[0636] H-[Si(R 1 )2-X] n1 -Si(R 1 )3…Equation (3)

[0637] In this context, X is independently either an oxygen atom or a carbon atom, and R... 1 Each is independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group, R 1 In the middle, at least 4 R1 It is a hydrolyzable group, a group with a hydrolyzable group, or a hydroxyl group, where n1 is an integer from 1 to 3.

[0638] X and R 1 Definition and X and R in group P 1 The definitions described herein are the same.

[0639] The intermediates disclosed herein are useful as intermediates for the compounds of this disclosure suitable for use in surface treatment agents.

[0640] Example

[0641] The present invention will be described in more detail below using examples, but the present invention is not limited to these examples. It should be noted that Examples 1 and 2 are comparative examples, and Examples 3 to 7 are exemplary examples.

[0642] [Synthesis of compound (11)]

[0643] Compound (11) was obtained according to the method described in International Publication No. 2023 / 017830. The average number of repeating units n was 17.

[0644]

[0645] [Synthesis of compound (12)]

[0646] Compound (12) was obtained according to the method described in International Publication No. 2023 / 017830. The average number of repeating units n was 17.

[0647]

[0648] [Synthesis of compound (13)]

[0649] Compound (13) was obtained according to the method described in International Publication No. 2021 / 187184. The average number of repeating units n was 17.

[0650]

[0651] [Synthesis of compound (14)]

[0652] Tris(triphenylphosphine)rhodium chloride (I) (0.05 g), toluene (30 g), and molecular sieve 5A (20 g) were added to trimethoxysilane (10 g) and refluxed at 110 °C for 24 hours. After removing the molecular sieve by filtration, the mixture was purified by distillation to obtain 2.5 g of compound (14). The structure of compound (14) was confirmed by the following NMR data.

[0653]

[0654] 1 H-NMR (400MHz, CDCl3) δ4.31(s, 1H), 3.68-3.55(m, 15H).

[0655] [Synthesis of compound (15)]

[0656] A toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and compound (14) (0.82 g) were added to compound (11) (0.85 g) dissolved in dichloromethane (10 g), and the mixture was stirred at 50 °C for 2 hours. The solvent was removed by vacuum distillation to give compound (15) 1.25. In compound (15), the average value of n was 17. The structure of compound (15) was confirmed by the following NMR data.

[0657]

[0658] 1 H-NMR (400MHz, CDCl3) δ3.76-3.26(m, 45H), 3.04(dd, J=6.0, 5.3Hz, 2H), 2.28-0.39(m, 38H), 0.20-0.24(m, 117H).

[0659] [Synthesis of compound (16)]

[0660] Compound (16) was obtained by following the method described in Japanese Patent Application Publication No. 2017-119849.

[0661]

[0662] [Synthesis of compound (17)]

[0663] THF (tetrahydrofuran, 10 g) was added to compound (16) (2.2 g) and homogenized. The mixture was then cooled to 0 °C, and 4.0 mL of butyllithium solution (THF solution, 1.6 M) was added. The mixture was stirred at 0 °C for 15 minutes. Next, hexamethylcyclotrisiloxane (8.0 g) was added, and the mixture was stirred at 25 °C for 12 hours. Then, dichlorodimethylsilane (1.5 g) was added, and the mixture was stirred at 25 °C for 1 hour. After extraction with hexane and water, low-boiling components were removed by vacuum distillation. The crude solution was subjected to rapid column chromatography using silica gel (developing solvent: hexane / ethyl acetate) to obtain compound (17) 3.7 g. In compound (17), the average value of n is 17. The structure of compound (17) was confirmed by the following NMR data.

[0664]

[0665] 1 H-NMR (400MHz, CDCl3) δ4.68-4.52(m, J=2.9Hz, 1H), 0.15-0.06(m, 6H), 0.05-0.06(m, 129H).

[0666] [Synthesis of compound (18)]

[0667] Hexamethoxydisiloxane (10 g) and toluene (10 g) were added to compound (17) (1 g) and stirred until homogeneous. Then, tris(pentafluorophenyl)borane (0.06 g) was added and stirred at 35 °C for 2 hours. The solvent and unreacted hexamethoxydisiloxane were removed by vacuum distillation to obtain compound (18) 1.1 g. In compound (18), the average value of n is 17. The structure of compound (18) was confirmed by the following NMR data.

[0668]

[0669] 1 H-NMR (400MHz, CDCl3) δ3.76-3.26(m, 15H), 0.25-0.16(m, 135H).

[0670] [Synthesis of compound (19)]

[0671] Compound (19) was obtained by following the method described in International Publication No. 2024 / 34669.

[0672]

[0673] [Synthesis of compound (20)]

[0674] A toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and compound (14) (0.82 g) were added to compound (19) (0.68 g) dissolved in dichloromethane (10 g), and the mixture was stirred at 50 °C for 2 hours. The solvent was removed by vacuum distillation, thereby yielding 1.14 g of compound (20). The structure of compound (20) was confirmed by the following NMR data.

[0675]

[0676] 1H-NMR (400MHz, CDCl3) δ 3.56 (d, J = 16.1 Hz, 30H), 3.03 (t, J = 5.6Hz, 2H), 2.19 (t, J = 8.5 Hz, 2H), 1.76 - 0.86 (m, 49H), 0.80 - 0.47 (m, 6H),0.05-0.06(m,21H).

[0677] [Synthesis of compound (21)]

[0678] A solution of dichloromethane (10 g), 1,1,1,3,3,5,5-heptamethyltrisiloxane (15 g), and a platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in toluene (platinum content: 3% by mass, 50 mg) was added to 18-bromo-1-octadecene (10 g) and stirred at 25 °C for 24 hours. After removing low-boiling components by vacuum distillation, rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 14 g of compound (21). The structure of compound (21) was confirmed by the following NMR data.

[0679]

[0680] 1 H-NMR (400 MHz, CDCl3) δ 3.41 (t, J = 6.9 Hz, 2H), 1.85 (dt, J =14.5, 7.0 Hz, 2H), 1.54 - 1.00 (m, 30H), 0.53 (dd, J = 9.4, 5.9 Hz, 2H), 0.25- -0.33 (m, 21H).

[0681] [Synthesis of compound (22)]

[0682] THF (20 g) and magnesium (1.1 g) were added to 11-bromo-1-undecene (10 g), and the mixture was stirred at 60 °C for 2 hours. The reaction solution was filtered to obtain 30 g of compound (22). The product was confirmed to have a concentration of 0.8 M by titration with 1,10-phenanthroline.

[0683]

[0684] [Synthesis of compound (23)]

[0685] THF (10 g), compound (22) (0.8 M) (10 mL), and copper(II) chloride (0.05 g) were added to compound (21) (1 g), and the mixture was stirred at 60 °C for 24 hours. Extraction was performed with hydrochloric acid and hexane, and low-boiling components were removed by vacuum distillation. Rapid column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane) was then performed to obtain compound (23) 0.4 g. The structure of compound (23) was confirmed by the following NMR data.

[0686]

[0687] 1 H-NMR (400 MHz, CDCl3) δ 5.82 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.10 - 4.81 (m, 2H), 2.12 - 1.90 (m, 2H), 1.54 - 1.00 (m, 50H), 0.52 (t, J =7.7 Hz, 2H), 0.25 - -0.33 (m, 21H).

[0688] [Synthesis of compound (24)]

[0689] A toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and compound (14) (0.72 g) were added to compound (23) (0.55 g) dissolved in dichloromethane (10 g), and the mixture was stirred at 50 °C for 2 hours. The solvent was removed by vacuum distillation, thereby yielding 1.14 g of compound (24). The structure of compound (24) was confirmed by the following NMR data.

[0690]

[0691] 1 H-NMR (400MHz, CDCl3) δ 3.56 (d, J = 16.1 Hz, 15H), 1.63 - 1.04 (m,54H), 0.81 - 0.43(m, 4H)., 0.25 - -0.33 (m, 21H).

[0692] [Synthesis of compound (25)]

[0693] To 1.0 g of 50 cSt monodisperse hydrogen-terminated polydimethylsiloxane (manufactured by Gelest Inc., product code: DMS-HM15), 10 g of hexamethoxydisiloxane and 10 g of toluene were added and stirred until homogeneous. Next, 0.06 g of tris(pentafluorophenyl)borane was added and the mixture was stirred at 35 °C for 2 hours. The solvent and unreacted hexamethoxydisiloxane were removed by vacuum distillation to obtain 1.4 g of compound (25). In compound (25), the average value of n is 45. The structure of compound (25) was confirmed by the following NMR data.

[0694]

[0695] 1 H-NMR (400MHz, CDCl3) δ 3.57 (d, J = 6.2 Hz, 30H), 0.25 - -0.33 (m,282H).

[0696] [Item crafting]

[0697] Articles of Examples 1 to 7 were obtained by surface treatment of a substrate using compounds (12), (13), (15), (18), (20), (24), and (25) using the following method. Wet coating was used as the surface treatment method.

[0698] 30g of silicon dioxide was placed in a copper furnace cylinder within a vacuum evaporation apparatus (ULVAC KIKO, Inc., VTR-350M) as the evaporation source. A glass substrate was placed inside the vacuum evaporation apparatus, and the air inside the apparatus was evaporated to a pressure of 5×10⁻⁶. -3 Pressure below Pa. The furnace cylinder is heated to about 2,000°C, and silicon oxide is vacuum-deposited on the surface of the substrate to produce a substrate with a silicon oxide layer having a thickness of about 20 nm.

[0699] A substrate with a silicon oxide layer was placed on the sample stage of a spray coating machine (API-90RS, Apeiros Co., Ltd.) with the silicon oxide layer as the surface. Next, a heptane solution (13g) containing 0.2% by mass of each of the above compounds was added to the syringe inside the spray coating machine, and spraying was performed at an atomization pressure of 130 kPa, a nozzle-sample surface distance of 50 mm, and a scanning speed of 300 mm / s (wet coating method). Then, the substrate with the silicon oxide layer coated with the compounds was heat-treated at 140°C for 30 minutes to obtain the evaluation samples (articles) of Examples 1 to 7, which are sequentially laminated with a substrate, a silicon oxide layer, and a surface treatment layer.

[0700] [evaluate]

[0701] Water repellency

[0702] Approximately 2 μL of distilled water was dropped onto the surface treatment layer of the item, and the initial water contact angle was measured using a contact angle measuring device (product name "DM-500", Kyowa Interface Science Co., Ltd.). The average value of the measurements taken at 5 points on the surface treatment layer was taken as the water contact angle. The water repellency of the surface treatment layer was evaluated based on the following criteria. It should be noted that the water contact angle was calculated using the 2θ method.

[0703] A: The initial water contact angle is above 105°.

[0704] C: The initial water contact angle is less than 105°

[0705] <Abrasion Resistance (Steel Wool)>

[0706] Regarding the surface treatment layer, according to JIS L0849:2013 (ISO: 105-X12:2001), a reciprocating traverse testing machine (manufactured by KNT) was used to test the water contact angle of Bonstar steel wool (#0000) after 10,000 reciprocating cycles at a pressure of 98.07 kPa and a speed of 320 cm / min. The method for determining the water contact angle after friction was set to be the same as the method for determining the initial water contact angle in the evaluation method of water repellency. The smaller the decrease in water repellency (water contact angle) after friction, the smaller the decrease in performance caused by friction, and the better the wear resistance. The evaluation criteria are as follows.

[0707] The decrease in water contact angle = (initial water contact angle) - (water contact angle after friction)

[0708] A: After 10,000 round trips, the water contact angle decreases to below 3°.

[0709] B: The decrease in water contact angle after 10,000 round trips exceeds 3° but is less than 5°.

[0710] C: The water contact angle decreases by more than 5° after 10,000 round trips.

[0711] Fingerprint Removal

[0712] Prepare a 1kg weight with a 2cm diameter red rubber plug to form the fingerprint impression. Next, add 70μL of artificial fingerprint liquid (manufactured by Isehisa Co., Ltd.) to a wiping cloth and allow the fingerprint to adhere in the artificial fingerprint liquid for 1 minute. To remove excess artificial fingerprint liquid adhering to the fingerprint, allow the fingerprint to adhere to a new wiping cloth for 20 seconds. Then, place an item with a surface treatment layer on a hot plate with the temperature set to 23°C. Imprint a fingerprint onto the surface treatment layer. Place the item with the artificial fingerprint liquid attached onto the sliding device (product name "HHS-2000", manufactured by Shinto Science Co., Ltd.). Using double-sided tape, attach a flat pressure head with a 1cm square area to a wiping cloth (manufactured by KB Seiren Co., Ltd., SavinaMinnimax) and place it on the sliding device. Wipe the adhered artificial fingerprint liquid in one direction with a load of 100g using the wiping cloth, facing the surface treatment layer. The haze of the wiped area was measured using a haze meter (product name "NDH7000SP", manufactured by Nippon Denshoku Co., Ltd.). The evaluation criteria are as follows.

[0713] A: Haze value is less than 0.1%

[0714] B: Haze value is 0.1% or higher but less than 1%.

[0715] C: Haze value above 1%

[0716] <Lightfastness>

[0717] For the surface treatment layer, a benchtop xenon arc lamp accelerated lightfastness testing machine (SUNTEST XLS+: product name, manufactured by Toyo Seiki Co., Ltd.) was used, with black panel temperature of 63°C, and light irradiation (650W / m²). 2 After 500 hours (300~700nm), the water contact angle of the surface treatment layer was measured using the method described above. The smaller the decrease in water contact angle after the lightfastness test, the smaller the decrease in performance caused by light, and the better the lightfastness of the surface treatment layer. The evaluation criteria are as follows.

[0718] The reduction in water contact angle = (initial water contact angle) - (water contact angle after lightfastness test)

[0719] A: Promotes a reduction in the water contact angle to below 3° after the lightfastness test.

[0720] B: Promotes a reduction in the water contact angle after lightfastness testing by more than 3° and less than 5°.

[0721] C: Promotes a reduction of more than 5° in the water contact angle after lightfastness testing.

[0722] [Table 1]

[0723]

[0724] As shown in Table 1, it was confirmed that the compounds of Examples 3-7, which have the P group, can form a surface treatment layer with excellent abrasion resistance compared to the compounds of Examples 1 and 2, which have the same structure but do not have the P group. Furthermore, it was also confirmed that the compounds of Examples 3-7 can form a surface treatment layer with excellent fingerprint removal and lightfastness compared to the compounds of Examples 1 and 2.

[0725] Industrial availability

[0726] The disclosed compounds are useful as surface treatment agents. These agents can be used, for example, as substrates in display devices such as touch panel displays, optical components, semiconductor components, building materials, automotive parts, and nanoimprint technology. Furthermore, they can be used in the bodies of transportation equipment such as trams, automobiles, ships, and airplanes, as well as in window glass (front windows, side windows, rear windows), rearview mirrors, and bumpers. Moreover, they can be used in outdoor items such as building exterior walls, tents, solar power modules, sound insulation panels, and concrete; fishing nets, insect nets, and sinks. Additionally, they can be used in kitchens, bathrooms, washbasins, mirrors, and toilet peripheral components; chandeliers, ceramics such as tiles; artificial marble, air conditioners, and various indoor equipment. Furthermore, they can be used as antifouling agents for jigs, interior walls, and piping in factories. Additionally, they can be used in goggles, eyeglasses, helmets, pinball machines, fibers, umbrellas, toys, and soccer balls. Finally, they can be used as anti-adhesion agents for various packaging materials such as food packaging materials, cosmetic packaging materials, and the interior of cans. In addition, surface treatment agents can be used in medical instruments such as car navigation systems, mobile phones, smartphones, digital cameras, digital camcorders, PDAs, portable audio players, car audio systems, game consoles, eyeglass lenses, camera lenses, lens filters, sunglasses, and gastroscopes, as well as in copiers, PCs, displays (such as liquid crystal displays, organic EL displays, plasma displays, and touch panel displays), touch panels, protective films, and anti-reflective films.

[0727] The application claims priority based on Japanese Special Application No. 2023-166268 filed on September 27, 2023, and includes all of its disclosures therein.

Claims

1. A compound comprising the group P and an organopolysiloxane residue, Group P: -[Si(R) 1 )2-X] n1 -Si(R 1 )3 in, X can be an oxygen atom or a carbon atom independently. R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group. R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group. n1 is an integer from 1 to 3.

2. The compound according to claim 1, wherein, The value of n1 is 1.

3. The compound according to claim 1, wherein, The group P is -[Si(OR)] 2 )2-O] n1 -Si(OR 2 )3, in, R 2 Each is an independent hydrocarbon group.

4. The compound according to claim 2, wherein, The group P is -Si(OR) 2 )2-O-Si(OR 2 )3, in, R 2 Each is an independent hydrocarbon group.

5. The compound represented by formula (1) or formula (2) below, [R 11 -(Q) r1 -Z 1 ] p1 -Q 1 -(J 1 ) n2 …Formula (1) (J 1 ) n2 -Q 2 -Z 2 -Q 2 -(J 1 ) n2 …Formula (2) in, J 1 Each of them independently represents the following group P, Group P: -[Si(R) 1 )2-X] n1 -Si(R 1 )3 X can be an oxygen atom or a carbon atom independently. R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group. R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group. n1 is an integer from 1 to 3. R 11 Each independently as (R 111 )3Si-, linear organopolysiloxane residues, cyclic organopolysiloxane residues, or cage-like organopolysiloxane residues, R 111 Each is independently a hydrocarbon group or a trialkylsilyloxy group. Q can be independently -O- or -OC(=O)-. r1 is independently either 0 or 1. Z 1 Each can be independently a single bond, an alkylene group optionally having an ether-like oxygen atom, an organopolysiloxane group, or a combination of an alkylene group optionally having an ether-like oxygen atom and an organopolysiloxane group. Z 2 It is an organopolysiloxane alkyl group, or a combination of an alkylene group having an ether-like oxygen atom and an organopolysiloxane alkyl group. Q 1 It is a (p1+n2) valence linking group. Q 2 Each is an independent linker with a valence of (1+n2). p1 is an integer greater than or equal to 1. Each of n2 is an integer greater than or equal to 1.

6. The compound according to claim 5, wherein, The n2 is an integer from 1 to 3.

7. The compound according to claim 5, wherein, The Z 1 -(Si(R) 8 )2-O) m -Si(R 8 )2-, in, R 8 Each is an independent hydrocarbon group. m is a number greater than or equal to 1.

8. The compound according to claim 5, wherein, The Z 2 -(Si(R) 8 )2-O) m -Si(R 8 )2-, in, R 8 Each is an independent hydrocarbon group. m is a number greater than or equal to 1.

9. A composition comprising the compound of any one of claims 1 to 8 and a liquid medium.

10. A surface treatment agent comprising the compound according to any one of claims 1 to 8.

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

12. A method for manufacturing an article, wherein, An article having a surface-treated layer formed on the substrate is manufactured by surface-treating a substrate with a surface-treated agent comprising any one of claims 1 to 8.

13. An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with a surface treatment agent comprising any one of claims 1 to 8.

14. The article according to claim 13, wherein it is an optical component.

15. The article of claim 13, wherein it is a display or a touch panel.

16. An intermediate represented by the following formula (3), H-[Si(R 1 )2-X] n1 -Si(R 1 )3…Formula (3) in, X can be an oxygen atom or a carbon atom independently. R 1 Each can be independently a hydrolyzable group, a group having a hydrolyzable group, a hydroxyl group, or a hydrocarbon group. R 1 In the middle, at least 4 R 1 It is a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group. n1 is an integer from 1 to 3.

17. The intermediate according to claim 16, wherein, The value of n1 is 1.

Images