Compound, composition, surface treatment agent, article and method for manufacturing article

Abstract

Provided are a novel compound and composition useful as a surface treatment agent capable of forming a surface treatment layer having excellent wear resistance on a substrate. A compound represented by formula (1-1) or formula (1-2). T-O-(Si (R2) 2-O) ma-Si (R2) 2-L1-L2-A-(Si (R) nL3-n) q (1-1), (L3-n (R) nSi) q-A-L2-L1-(Si (R2) 2-O) mb-Si (R2) 2-L1-L2-A-(Si (R) nL3-n) q (1-2).

Description

TECHNICAL FIELD

[0001] The present application relates to a compound, a composition, a surface treatment agent, an article, and a method for manufacturing an article. BACKGROUND

[0002] In recent years, in order to improve the appearance, the visibility, and the like, a technique for making the surface of an article less likely to attach fingerprints, and a technique for easily removing stains are required. As a specific method, a method of performing surface treatment on the surface of an article using a surface treatment agent is known.

[0003] For example, a silane compound having a specific siloxane group for the above-described surface treatment agent is described in Patent Literature 1.

[0004] PRIOR ART DOCUMENTS

[0005] PATENT LITERATURE

[0006] Patent Literature 1: International Publication No. 2023 / 017830 SUMMARY

[0007] PROBLEMS TO BE SOLVED BY THE INVENTION

[0008] On the other hand, a surface treatment layer is formed using the silane compound described in Patent Literature 1, and as a result, it is found that the abrasion resistance of the formed surface treatment layer needs to be further improved.

[0009] The present application was completed in view of such circumstances, and an object of one embodiment of the present application is to provide a novel compound and a composition useful as a surface treatment agent capable of forming a surface treatment layer excellent in abrasion resistance on a substrate.

[0010] An object of one embodiment of the present application is to provide a surface treatment agent capable of forming a surface treatment layer excellent in abrasion resistance on a substrate.

[0011] An object of one embodiment of the present application is to provide an article having a surface treatment layer excellent in abrasion resistance and a method for manufacturing an article.

[0012] MEANS FOR SOLVING PROBLEMS

[0013] The present application includes the following modes. [1]

[0015] A compound represented by the formula (1-1) described later or the formula (1-2) described later. [2]

[0017] The compound according to [1], in which, in the formula (1-1) and the formula (1-2), -A- (Si (R) n L 3-n )q the group represented by formula (3-1A) described later. [3]

[0019] The compound according to [1] or [2], wherein L 1 is a single bond or alkylene. [4]

[0021] The compound according to any one of [1] to [3], wherein L 1 is a single bond. [5]

[0023] The compound according to any one of [1] to [4], wherein maand mbare each independently a number of 2 to 600. [6]

[0025] The compound according to any one of [1] to [5], wherein q is an integer of 1 to 4. [7]

[0027] A composition comprising the compound according to any one of [1] to [6], and comprising a liquid medium. [8]

[0029] A surface treatment agent comprising the compound according to any one of [1] to [6]. [9]

[0031] A surface treatment agent comprising the compound according to any one of [1] to [6], and comprising a liquid medium.

[10]

[0033] A method for manufacturing an article, wherein a surface treatment agent according to [8] is used to perform surface treatment on a substrate, to manufacture an article having a surface treatment layer formed on the substrate.

[11]

[0035] An article comprising a substrate and a surface treatment layer, the surface treatment layer being disposed on the substrate and having been subjected to surface treatment with a surface treatment agent according to [8].

[12]

[0037] The article according to

[11] , which is an optical member.

[13]

[0039] The article according to

[11] , which is a display or a touch panel.

[14]

[0041] A method for manufacturing an article, wherein a substrate is surface-treated using the surface treatment agent described in [9] to manufacture an article having a surface-treated layer formed on the substrate.

[15]

[0043] An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent described in [9].

[16]

[0045] According to

[15] , the item is an optical component.

[17]

[0047] According to

[15] , the item is a display or touch panel.

[0048] The effects of the invention

[0049] According to one embodiment of the present invention, novel compounds and compositions are provided as surface treatment agents that are useful as surface treatment agents capable of forming a surface treatment layer with excellent wear resistance on a substrate.

[0050] According to one embodiment of the present invention, a surface treatment agent is provided that is capable of forming a surface treatment layer with excellent wear resistance on a substrate.

[0051] According to one embodiment of the present invention, an article having a surface treatment layer with excellent wear resistance and a method for manufacturing the article are provided. Detailed Implementation

[0052] In this specification, the numerical range represented by "~" contains the minimum and maximum values ​​before and after "~".

[0053] In the numerical ranges described in this specification, the upper or lower limit of one numerical range can be replaced with the upper or lower limit of another numerical range described in other stages. Furthermore, the upper or lower limit of the numerical range described in this specification can also be replaced with the values ​​shown in the embodiments.

[0054] In this specification, "surface treatment layer" refers to a layer formed on the surface of a substrate through surface treatment.

[0055] In this specification, when a compound or group is represented by a specific formula (X), the compound or group represented by the formula (X) is sometimes referred to as compound (X) or compound X, and group (X) or group X, respectively.

[0056] In this specification, methyl groups are sometimes referred to as "Mt" and ethyl groups as "Et".

[0057] 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".

[0058] [Compound]

[0059] The compounds of the present invention are those represented by formula (1-1) or formula (1-2) described later. In this specification, the compounds of the present invention refer to at least one of the compounds represented by formula (1-1) and the compounds represented by formula (1-2).

[0060] When the compounds of the present invention are used, a surface treatment layer with excellent wear resistance can be formed. The reason for this is not yet clear, but it is speculated as follows.

[0061] In the compounds of the present invention, L is present at specific sites. 2 The groups shown, when evaluating wear resistance, L 2 The groups shown have high bond energies, making it difficult for bonds to break, thus it is believed that a surface treatment layer with excellent wear resistance can be formed.

[0062] The compounds of the present invention will now be described in detail.

[0063] <The compound shown in formula (1-1)>

[0064] TO-(Si(R) 2 )2-O) ma -Si(R) 2 )2-L 1 -L 2 -A-(Si(R)) n L 3-n ) q (1-1)

[0065] In equation (1-1),

[0066] T is (R) 1 ) 3Si-, monovalent cyclic polysiloxane residues or monovalent cage-like polysiloxane residues,

[0067] R 1 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0068] R 2 Each is an independent hydrocarbon group.

[0069] L 1 It is a single bond or a divalent linker.

[0070] L 2 For -CH=CH-, -C≡C-, or -C(=CH2)-,

[0071] A is a single bond or a (q+1) valence linker.

[0072] R are each an independent hydrocarbon group.

[0073] L can be a hydrolyzable group, a group with a hydrolyzable group, or a hydroxyl group, each independently.

[0074] ma is a number greater than or equal to 0.

[0075] mb is a number greater than or equal to 1.

[0076] n are independent integers from 0 to 2.

[0077] Each q is an integer greater than or equal to 1.

[0078] In equation (1-1), T is (R 1 ) 3Si-, monovalent cyclic polysiloxane residues or monovalent cage-like polysiloxane residues.

[0079] As R 1 The hydrocarbon group shown can be, for example, an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group. The alkyl group can be any one of a straight-chain alkyl group, a branched alkyl group, and a cyclic alkyl group, and is preferably a straight-chain alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 4. As R 1 The hydrocarbon group shown is more preferably methyl, ethyl, n-propyl or n-butyl, and even more preferably methyl.

[0080] R 1 The alkyl group contained in the trialkylsilyloxy group shown can be any one of straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably a straight-chain alkyl. R 1 The number of carbon atoms in the alkyl group of the trialkylsilyloxy group shown is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. As R 1 The alkyl group contained in the trialkylsiloxy group shown is more preferably methyl, ethyl, n-propyl or n-butyl, and even more preferably methyl.

[0081] Multiple R 1 They can be the same or different from each other; from the point of view of ease of manufacturing, the same is preferred.

[0082] As (R) 1The group represented by 3Si-, for example, includes methyl diethylsilyl, methyl ethylpropylsilyl, methyl ethyl butylsilyl, methyl dipropylsilyl, methyl propyl butylsilyl, methyl dibutylsilyl, dimethyl ethylsilyl, dimethyl propylsilyl, dimethyl butylsilyl, trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, and trialkylsiloxy groups having these groups.

[0083] From the perspective of improving the water repellency of the surface treatment layer, R 1 The preferred form is a straight-chain alkyl group, more preferably methyl, ethyl, n-propyl or n-butyl, and even more preferably methyl.

[0084] The monovalent cyclic polysiloxane residues are preferably groups represented by formula (T1).

[0085] [Chemistry 1]

[0086]

[0087] In equation (T1),

[0088] R 3 Each is independently a hydrocarbon group, a hydrocarbon group with substituents, or -O-SiR. 51 The group shown in 3,

[0089] s is an integer from 1 to 4.

[0090] R 51 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0091] This indicates the bonding location.

[0092] As R 3 The hydrocarbon groups shown may include, for example, aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Preferably, the hydrocarbon group is an aliphatic hydrocarbon group, and more preferably an alkyl group.

[0093] As R 3 The alkyl group shown can be any of straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably a 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. Specifically, R 3 The alkyl group shown is preferably methyl, ethyl, n-propyl, n-butyl, isobutyl, or heptyl, and more preferably methyl.

[0094] As R 3The hydrocarbon groups contained in the substituted hydrocarbon groups shown may include, for example, aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group. The alkyl group can be any one of straight-chain alkyl, branched alkyl, and cyclic alkyl, and is preferably a straight-chain alkyl. The alkyl group contained in the substituted alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 8, and even more preferably 2 to 4.

[0095] As R 3 Substituents in the substituted hydrocarbon groups shown include, for example, halogen atoms, hydroxyl groups, alkoxy groups, trialkylsilyl ethers, trialkylsilyl groups, amino groups, nitro groups, cyano groups, sulfonyl groups, trifluoromethyl groups, and -SiR groups. 52 The group shown in 3. R 52 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0096] As R 52 The hydrocarbon groups shown can be listed as having the same characteristics as R. 3 The same group as the hydrocarbon group shown.

[0097] As R 52 The alkyl group contained in the trialkylsiloxy group shown can be any one of straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably a straight-chain alkyl. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 8, further preferably 1 to 4, and particularly preferably 1. The three alkyl groups contained in the trialkylsiloxy group may be the same or different from each other.

[0098] 3 Rs 52 They can be the same or different from each other; from the point of view of ease of manufacturing, the same is preferred.

[0099] R 3 The figure shown is composed of -O-SiR 51 In the group represented by 3, R 51 Each is independently a hydrocarbon group or a trialkylsilyloxy group. As R 51 The hydrocarbon groups shown can be listed as having the same characteristics as R. 3 The same group as the hydrocarbon group shown. As R 51 The trialkylsilyloxy group shown can be listed as having a relationship with R. 52 The trialkylsilyloxy group shown is the same as the group shown.

[0100] Multiple R 3 They can be the same or different from each other; from the point of view of ease of manufacturing, the same is preferred.

[0101] Examples of monovalent cyclic polysiloxane residues include the following groups. This indicates the bonding location.

[0102] [Chemistry 2]

[0103]

[0104] [Chemistry 3]

[0105]

[0106] The monovalent cage-like polysiloxane residues are preferably groups represented by formula (T2).

[0107] [Chemistry 4]

[0108]

[0109] In equation (T2),

[0110] R 4 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0111] This indicates the bonding location.

[0112] As R 4 The hydrocarbon group shown can be, for example, an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The hydrocarbon group is preferably an aliphatic hydrocarbon group, and more preferably an alkyl group. The alkyl group can be any one of a straight-chain alkyl group, a branched alkyl group, and a cyclic alkyl group, preferably a straight-chain alkyl group or a branched alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 4. As R 4 The hydrocarbon group shown is more preferably methyl, ethyl, n-propyl, n-butyl or isobutyl, and isobutyl is even more preferred.

[0113] R 4 The alkyl group contained in the trialkylsilyloxy group shown can be any one of straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably a straight-chain alkyl. R 4 The number of carbon atoms in the alkyl group of the trialkylsilyloxy group shown is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4. As R 1 The hydrocarbon group shown is more preferably methyl, ethyl, n-propyl or n-butyl, and even more preferably methyl.

[0114] Multiple R 4 They can be the same or different from each other; from the point of view of ease of manufacturing, the same is preferred.

[0115] Examples of monovalent cage-like polysiloxane residues include the following groups. This indicates the bonding location.

[0116] [Chemistry 5]

[0117]

[0118] In equation (1-1), R 2 Each is an independent hydrocarbon group.

[0119] As R 2 Examples of R can be listed. 1 The hydrocarbon group is indicated. Preferably, the hydrocarbon group is an aliphatic hydrocarbon group, more preferably an alkyl group. The alkyl group can be any one of straight-chain alkyl, branched alkyl, and cyclic alkyl, preferably a straight-chain alkyl. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 4. As R 2 More preferably methyl, ethyl, n-propyl or n-butyl, and even more preferably methyl.

[0120] R 2 The number of carbon atoms is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.

[0121] In equation (1-1), L 1 It is a single bond or a divalent linker.

[0122] 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.

[0123] The aforementioned divalent hydrocarbon group can be a divalent saturated hydrocarbon group or a divalent aromatic hydrocarbon group. The divalent saturated hydrocarbon group can be straight-chain, branched, or cyclic; for example, alkylene groups are listed. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, further preferably 4 to 20, and particularly preferably 5 to 15. As a divalent aromatic hydrocarbon group, a divalent aromatic hydrocarbon group with 5 to 20 carbon atoms is preferred; for example, phenylene groups are listed.

[0124] As L 1 Preferred single bonds or divalent saturated hydrocarbon groups, more preferably single bonds or alkylene groups, and from the viewpoint of superior wear resistance, single bonds or alkylene groups with 3 to 15 carbon atoms are further preferred.

[0125] In equation (1-1), L 2 It can be -CH=CH-, -C≡C-, or -C(=CH2)-.

[0126] As L 2 From the perspective of superior wear resistance, -CH=CH- or -C≡C- are preferred.

[0127] In equation (1-1), each R is an independent hydrocarbon group.

[0128] As a hydrocarbon group represented by R, for example, R can be listed. 1 The hydrocarbon group shown.

[0129] In formula (1-1), L is independently a hydrolyzable group, a group having a hydrolyzable group, or a hydroxyl group.

[0130] Hydrolyzable groups are groups that become hydroxyl groups through hydrolysis. That is, hydrolyzable silane groups (represented by Si-L) undergo hydrolysis to become silanol groups (represented by Si-OH). The silanol groups further react with each other to form Si-O-Si bonds. Alternatively, silanol groups can undergo dehydration condensation reactions with silanol groups from oxides present on the substrate surface to form Si-O-Si bonds.

[0131] Examples of hydrolyzable groups include alkoxy groups, aryloxy groups, halogen atoms, acyl groups, acyloxy groups, and isocyanate groups (-NCO). Alkoxy groups are preferably alkoxy groups with 1 to 4 carbon atoms. Aryloxy groups are preferably aryloxy groups with 3 to 10 carbon atoms. The aryl group in an aryloxy group includes heteroaryl groups. Halogen atoms are preferably chlorine atoms. Acyl groups are preferably acyl groups with 1 to 6 carbon atoms. Acyloxy groups are preferably acyloxy groups with 1 to 6 carbon atoms.

[0132] 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 For alkylene groups that can have ether-like oxygen atoms, L B It is a hydrolyzable group.

[0133] The alkylene group preferably has 1 to 10 carbon atoms.

[0134] L A The alkylene groups shown above may have ether-like oxygen atoms between carbon atoms. The number of these ether-like oxygen atoms can be one or more. A When it is an alkylene group with an ether-like oxygen atom, it is related to -OL. A -L B The atom with the -O- side bond is preferably a carbon atom constituting an alkylene group having an ether-like oxygen atom.

[0135] L B The hydrolyzable groups shown have the same meaning as the hydrolyzable groups shown in L above, and the preferred methods are also the same.

[0136] From the viewpoint of ease of compound manufacture, L is preferably an alkoxy or halogen atom with 1 to 4 carbon atoms. From the viewpoint of less degassing during coating and better storage stability of the compound, L is preferably an alkoxy with 1 to 4 carbon atoms, and more preferably an ethoxy or methoxy atom.

[0137] In equation (1-1), ma is a number greater than or equal to 0.

[0138] It should be noted that T is R 1 All are trialkylsilyloxy (R 1 When 3Si-, ma is preferably a number greater than or equal to 0. Additionally, T is R. 1 At least one of them is a hydrocarbon group (R) 1 When the residue is a 3Si-, monovalent cyclic polysiloxane residue or a monovalent cage-like polysiloxane residue, ma is preferably 1 or more.

[0139] ma is preferably a number from 2 to 600, more preferably a number from 3 to 500, even more preferably a number from 9 to 50, particularly preferably a number from 11 to 30, and most preferably a number from 11 to 25.

[0140] In equation (1-1), n ​​is an integer from 0 to 2.

[0141] n is preferably 0 or 1, more preferably 0. By having multiple L's, the surface treatment layer adheres more firmly to the substrate.

[0142] When n is 1 or less, the multiple Ls present in one molecule may be either the same or different. From the viewpoint of ease of obtaining the raw materials and ease of manufacturing the compound, it is preferable that the multiple Ls are the same. When n is 2, the multiple Rs present in one molecule may be either the same or different. From the viewpoint of ease of obtaining the raw materials and ease of manufacturing the compound, it is preferable that the multiple Rs are the same.

[0143] In equation (1-1), q is an integer greater than or equal to 1.

[0144] From the perspective of improving the wear resistance of the surface treatment layer, q is preferably an integer from 1 to 15, more preferably an integer from 1 to 6, even more preferably an integer from 1 to 4, and particularly preferably 2 or 3. q can be 1.

[0145] When q is an integer greater than 2, multiple [Si(R)] n L 3-n They can be the same or different from each other.

[0146] In formula (1-1), A is a single bond or a (q+1) valence linking group.

[0147] As A, any group that does not impair the effects of the present invention may be used. Examples include alkylene groups, carbon atoms, nitrogen atoms, silicon atoms, organopolysiloxane residues having ether oxygen atoms or divalent alkylene oxide residues, organopolysiloxane residues with 2 to 8 valent alkylene oxide residues, and groups from which Si(R) has been removed from formulas (3-1A), (3-1B), and (3-1A-1) to (3-1A-7) described below. n L 3-n . group.

[0148] Alternatively, A can be one of the groups (g2-1) to (g2-14) described later.

[0149] In equation (1-1), -A(Si(R)) n L 3-n ) q The indicated group is preferably group (3-1A) or group (3-1B), more preferably group (3-1A).

[0150] -Q a -X 31 (-Q) b -Si(R) n L 3-n ) h (-R) 31 ) i (3-1A)

[0151] -Q c -[CH2C(R) 32 (-Q) d -Si(R) n L 3-n )] y -R 33 (3-1B)

[0152] It should be noted that in equations (3-1A) and (3-1B), R, L and n are defined as described above.

[0153] In formula (3-1A), Q a It is a single bond or a divalent linker.

[0154] 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.

[0155] The divalent hydrocarbon group described above can be a divalent saturated hydrocarbon group or a divalent aromatic hydrocarbon group. The divalent saturated hydrocarbon group can be linear, branched, or cyclic, and examples include alkylene groups. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, further preferably 4 to 20, and particularly preferably 5 to 15. In addition, as a divalent aromatic hydrocarbon group, a group with 5 to 20 carbon atoms is preferred, and examples include phenylene groups.

[0156] 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).

[0157] It should be noted that, as examples of groups formed by combining two or more of these elements, such as -C(O)O-, -C(O)S-, and -C(O)N(R) d )-、-N(R d C(O)N(R) d )-、-N(R d C(O)O-, -SO2N(R) d -、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-, alkylenes with -N(R) d )-alkylene groups, having -N(R d C(O)N(R) d )-alkylene groups, having -SO2N(R d )-alkylene and alkylene-Si(R a )2-Phenylidene-Si(R a 2.

[0158] Among them, Q a Preferably, it is a divalent hydrocarbon group (preferably an alkylene group), a divalent heterocyclic group, -O-, -S-, -SO2-, or -N(R) group. d -, -C(O)-, -Si(R) a )2-, -C(O)O-, -C(O)S-, -C(O)N(R d )-、-N(R d C(O)N(R) d )-、-N(R d C(O)O-, -SO2N(R) d -、Having -C(O)N(R) d )-alkylene groups, having -OC(O)N(R dAlkylenes with -S-, 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 of -C(O)O-, more preferably -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-, 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.

[0159] In addition, Q a Preferably, 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 alkylene groups having -C(O)O-, alkylene groups having -SO2N(R) d )-alkylene, or alkylene-Si(R a )2-Phenylidene-Si(R a )2, more preferably -C(O)-. R a and R d The definition is as described above.

[0160] In equation (3-1A), X 31 It can be a single bond, alkylene group, nitrogen atom, carbon atom, silicon atom, organopolysiloxane residue with 2 to 8 valences, or a cyclic group with (h+i+1) valences.

[0161] It should be noted that the aforementioned alkylene groups may have -O-, silylene skeleton groups, divalent organopolysiloxane residues, or dialkylsilyl groups. Alkylene groups may have multiple groups selected from the group consisting of -O-, silylene skeleton groups, divalent organopolysiloxane residues, and dialkylsilyl groups.

[0162] X 31The number of carbon atoms in the alkylene group shown can be 1~60, 1~30, 1~20, or 1~10.

[0163] Examples of organopolysiloxane residues with valences of 2 to 8 include divalent organopolysiloxane residues and (w+1)valent organopolysiloxane residues, which will be described later.

[0164] In equation (3-1A), X 31 When Q is a cyclic group with a valence of (h+i+1), a 、(-Q b -Si(R) n L 3-n ) and R 31 It is directly bonded to the atoms that make up the ring. This ring is a ring other than the organopolysiloxane ring.

[0165] X 31 The ring can be any of a monocyclic, fused polycyclic, bridged, spirocyclic, or aggregated polycyclic ring. 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.

[0166] As a monocyclic ring, 4- to 8-membered rings are preferred, and 5- and 6-membered rings are more preferred. As a fused polycyclic ring, a fused polycyclic ring formed by fusion of two or more 4- to 8-membered rings is preferred, a fused polycyclic ring formed by bonding two or three rings selected from 5- and 6-membered rings is more preferred, and a fused polycyclic ring formed by bonding one or two rings selected from 5- and 6-membered rings with one 4-membered ring is also preferred. As a bridging ring, a bridging ring with a 5- or 6-membered ring as the largest ring is preferred, and a spiro ring formed by two 4- to 6-membered rings is preferred. As an aggregated polycyclic ring, an aggregated polycyclic ring formed by bonding two or three rings selected from 5- and 6-membered rings through a single bond, 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 -Si(R) n L 3-n ) and R 31 Any one of (i=1 or higher).

[0167] 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.

[0168] As X 31The ring in the compound is preferably selected from the following groups based on the aspects of easy compound manufacturing and superior wear resistance of the surface treatment layer: 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 2 or more of these rings with single bonds as the connecting groups and alkylene groups, oxygen atoms or sulfur atoms with 3 or fewer carbon atoms.

[0169] Preferred rings are benzene rings, aliphatic rings of 5-membered or 6-membered rings, heterocyclic rings of 5-membered or 6-membered rings having nitrogen or oxygen atoms, and fused rings of 5-membered or 6-membered carbon rings and heterocyclic rings of 4-6-membered rings.

[0170] As X 31 The rings in this context include, for example, the rings shown below, 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.

[0171] [Chemistry 6]

[0172]

[0173] Composition of X 31 The non-ring-forming connecting bonds between the atoms of the ring in the middle are with Q. a 、(-Q b -Si(R) n L 3-n ) 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).

[0174] In addition, one carbon atom forming the ring has two atoms related to Q. a 、(-Q b -Si(R) n L 3-n ) or R 31 In the case of a bonded linkage, Q can be bonded to this single carbon atom. a and (-Q b -Si(R) n L 3-n ), or you can bond two (-Q) b -Si(R) nL 3-n ). Preferred Q a With (-Q) b -Si(R) n L 3-n ) or R 31 Bonded to different ring-forming atoms. h (-Q) b -Si(R) n L 3-n () can bond to different cyclic atoms, and two of them can bond to one cyclic carbon atom, thus the two (-Q) bonds can bond to each other. b -Si(R) n L 3-n A ring-shaped carbon atom formed by bonding can consist of more than two R atoms. 31 They can bond to different cyclic atoms, with two of them bonding to one cyclic carbon atom, thus forming two R atoms. 31 There can be more than two carbon atoms in a cyclic ring formed by bonding.

[0175] From the perspective of improving the wear resistance of the surface treatment layer, X 31 Preferably, it is a nitrogen atom, a carbon atom, a silicon atom, an organopolysiloxane residue with a valence of 4 to 8, or a cyclic group with a valence of (h+i+1), and more preferably a carbon atom.

[0176] In formula (3-1A), Q b It is a single bond or a divalent linker.

[0177] The definition of a divalent linker is the same as that of Q above. a The definitions described herein are the same.

[0178] Among them, Q b Preferably, the alkylene group has an ether-like oxygen atom. The alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, even more preferably 2 to 20, but can be 2 to 10, 2 to 6, or 2 to 5. Examples include 2, 3, 8, 9, and 11. Alternatively, the number of carbon atoms can be 1 to 10.

[0179] In equation (3-1A), R 31 It can be a hydrogen atom, a hydroxyl group, or an alkyl group.

[0180] Alkyl groups can be any of straight-chain, branched, and cyclic, with straight-chain being preferred.

[0181] The alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3, and even more preferably 1.

[0182] X 31 When the bond is a single bond or an alkylene group, h is 1 and i is 0.

[0183] X31 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.

[0184] 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.

[0185] X 31 When the residues are 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=1~7.

[0186] X 31 When the group is a ring 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.

[0187] (-Q) b -Si(R) n L 3-n When there are two or more (-Q) b -Si(R) n L 3-n (R) can be the same or different. 31 When there are two or more, the two or more (-R) 31 They can be the same or different.

[0188] From the perspective of improving the wear resistance of the surface treatment layer, i is preferably 0.

[0189] In equation (3-1A), in Q a X 31 and Q b In the case of a single bond, [Si(R)] n L 3-n ] and L 2 Direct bonding.

[0190] In equation (3-1B), Q c It is a single bond or a divalent linker.

[0191] The definition of a divalent linker is the same as that of Q above. a The definitions described herein are the same.

[0192] In equation (3-1B), R 32 The atom is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; from the perspective of ease of compound production, a hydrogen atom is preferred.

[0193] As an alkyl group, methyl is preferred.

[0194] In equation (3-1B), Q dIt 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-.

[0195] 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.

[0196] y is an integer from 1 to 10, preferably an integer from 1 to 6.

[0197] Two or more [CH2C(R)] 32 (-Q) d -Si(R) n L 3-n [The characters] can be the same or different.

[0198] As a group (3-1A), groups (3-1A-1) to (3-1A-7) are preferred.

[0199] -L 3 -(X) 32 ) s1 -Q b1 -Si(R) n L 3-n (3-1A-1)

[0200] -L 3 -(X) 33 ) s2 -Q a2 -N[-Q b2 -Si(R) n L 3-n ]2 (3-1A-2)

[0201] -Q a3 -Si(R) g )[-Q b3 -Si(R) n L 3-n ]2 (3-1A-3)

[0202] -L 3 -[Q e ] s4 -Q a4 -(O) t4 -C[-(O) u4 -Q b4 -Si(R) n L 3-n ] 3-w1 (-R) 31 ) w1 (3-1A-4)

[0203] -Q a5 -Si[-Q b5 -Si(R) n L 3-n ]3 (3-1A-5)

[0204] -L 3 -[Q e ] v -Q a6 -Z a [-Q b6 -Si(R) n L 3-n ] w2 (3-1A-6)

[0205] -L 3 -[Q e ] s4 -Q a4 -(O) t4 -Z c [-(OQ b4 ) u4 -Si(R) n L 3-n ] w3 (-OH) w4 (3-1A-7)

[0206] It should be noted that in equations (3-1A-1) to (3-1A-7), R, L and n are defined as described above.

[0207] Wherein, the group (3-1A) is preferably the group (3-1A-1) or the group (3-1A-4), more preferably the group (3-1A-4).

[0208] In equations (3-1A-1)~(3-1A-2) and (3-1A-4)~(3-1A-7), L 3 It is a single bond or an alkylene group.

[0209] As the aforementioned alkylene group, for example with Q a The alkylene groups shown have the same meaning and the preferred method is also the same.

[0210] 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 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).

[0211] R d The definition is as described above.

[0212] s1 is either 0 or 1.

[0213] Among them, X 32 Preferably -O-, -S-, -N(R) d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-、-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 )-.

[0214] Q b1 It can be a single bond or an alkylene group. Additionally, the alkylene group can have -O-, a silylene skeleton group, or a dialkylsilyl group. The alkylene group can have multiple groups selected from the group consisting of -O-, silylene skeleton groups, divalent organopolysiloxane residues, and dialkylsilyl groups.

[0215] It should be noted that, in the case where the alkylene group has -O-, silylene skeleton group, divalent organopolysiloxane residue or dialkylsilyl group, these groups are preferably present between carbon atoms.

[0216] Q b1 The alkylene group shown 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 number of carbon atoms can be 1 to 10.

[0217] Where s1 is preferably 1, Q b1 Preferably, it is an alkylene group having 2 to 6 carbon atoms.

[0218] In addition, s1 is preferably 0, Q b1 Preferably, it is an alkylene group having 2 to 6 carbon atoms.

[0219] As a group (3-1A-1) [-(X 32 ) s1 -Q b1 -Si(R) n L 3-n For example, the following groups can be listed. In the following formula, To be with L 3 The bonding positions.

[0220] [Chemistry 7]

[0221]

[0222] [Chemistry 8]

[0223]

[0224] 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 C(O)-, -N(R) d C(O)N(R) d -, -OC(O)N(R) d - or -C(O)N(R) d )-.

[0225] R d The definition is as described above.

[0226] s2 is either 0 or 1. From the perspective of ease of compound production, s2 is preferably 0.

[0227] Among them, X 33 Preferably -O-, -S-, -N(R) d )-, -C(O)-, -C(O)O-, -C(O)S-, -SO2N(R d )-、-N(R d C(O)-, -N(R) d C(O)N(R) d -, -OC(O)N(R) d - or -C(O)N(R) d )-.

[0228] Q a2 It is a single bond, alkylene, -C(O)-, or an etheric oxygen atom between carbon atoms of alkylene with more than 2 carbon atoms, -C(O)-, -C(O)O-, -C(O)N(R) d )-、-N(R dC(O)N(R) d )-、-N(R d C(O)O-, -SO2N(R) d -, -C(O)N(R) d )- or -NH- groups.

[0229] R d The definition is as described above.

[0230] Q a2 The number of carbon atoms in the alkylene group shown is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 3.

[0231] Q a2 The alkylene groups shown have etheric oxygen atoms, -C(O)-, -C(O)O-, or -C(O)N(R) between carbon atoms. d )-、-N(R d C(O)N(R) d )-、-N(R d C(O)O-, -SO2N(R) d -, -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.

[0232] From the perspective of ease of compound production, Q a2 Single bonds are preferred.

[0233] Q b2 It is an alkylene group, or an organopolysiloxane residue, an ether oxygen atom, or a -NH- group between carbon atoms of an alkylene group having two or more carbon atoms.

[0234] Q b2 The alkylene group shown 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.

[0235] Q b2 The number of carbon atoms in the alkylene group having a divalent organopolysiloxane residue, an ether oxygen atom, or a -NH- group between carbon atoms is preferably 2 to 10, more preferably 2 to 6.

[0236] As Q b2 From the perspective of ease of compound production, -CH2CH2CH2- and -CH2CH2OCH2CH2CH2- (where the right side is bonded to Si) are preferred.

[0237] 2 [-Q] b2 -Si(R) n L 3-n They can be the same or different.

[0238] As a group (3-1A-2) [-(X 33 ) s2 -Q a2 -N[-Q b2 -Si(R) n L 3-n ]2], for example, the following groups can be listed. In the following formula, To be with L 3 The bonding positions.

[0239] Additionally, in the formula, (CH2) is bonded to the reactive silane group. α In this context, α is an integer representing 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. For example, 2, 3, 8, 9, and 11 can be listed. Furthermore, the number of carbon atoms can be 1 to 10. The multiple α groups contained in the same compound can be the same or different, but are preferably the same. For example, all the multiple α groups contained in the same compound are 2, 3, 8, 9, and 11. The same applies below.

[0240] [Chemistry 9]

[0241]

[0242] [Chemistry 10]

[0243]

[0244] 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.

[0245] The number of carbon atoms in the alkylene group having an ether-like oxygen atom is preferably 1 to 10, more preferably 2 to 6.

[0246] R g It can be a hydrogen atom, a hydroxyl group, or an alkyl group.

[0247] 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.

[0248] Q b3A group that is an alkylene group, or an alkylene group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms.

[0249] Q b3 The alkylene group shown 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. For example, 2, 3, 8, 9, and 11 are listed. In addition, the number of carbon atoms mentioned above can be 1 to 10.

[0250] Q b3 The number of carbon atoms in the alkylene group having an etheric oxygen atom or a divalent organopolysiloxane residue between carbon atoms is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0251] From the perspective of ease of compound production, Q b3 Preferably, it is -CH2CH2-, -CH2CH2CH2-, or -CH2CH2CH2CH2CH2CH2CH2CH2-.

[0252] 2 [-Q] b3 -Si(R) n L 3-n They can be the same or different.

[0253] As a functional group (3-1A-3), the following functional groups can be listed as examples. In the following formula, To be with L 2 The bonding positions.

[0254] [Chemistry 11]

[0255]

[0256] [Chemistry 12]

[0257]

[0258] In group (3-1A-4), Q e is -C(O)O-, -SO2N(R d - or -N(R) d )C(O)-.

[0259] R 31 The definition is as described above. When w1 is 1 or 2, R... 31 Hydrogen atoms are preferred.

[0260] s4 is either 0 or 1.

[0261] Q a4It is a single bond, or optionally an alkylene group having an ether-like oxygen atom.

[0262] 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, further preferably 1 to 6, and particularly preferably 1 to 3.

[0263] t4 is 0 or 1 (where Q is 0 or 1). a4 (0 when it is a single bond).

[0264] As -Q a4 -(O) t4 From the perspective of ease of compound preparation, when s4 is 0, the preferred configurations are single bonds, -CH2O-, -CH2OCH2-, -CH2OCH2CH2O-, -CH2OCH2CH2OCH2-, or -CH2OCH2CH2CH2CH2OCH2- (wherein the left side is related to (XO)). m (Bonding). When s4 is 1, a single bond, -CH2- or -CH2CH2- is preferred.

[0265] Q b4 The alkylene group is optionally -O-, -C(O)N(R) d )-(R d (as defined above), silymine skeleton group, divalent organopolysiloxane residue or dialkylmethylenesilyl group.

[0266] It should be noted that when the alkylene group has an -O- or silanine skeleton group, it is preferable to have an -O- or silanine skeleton group between carbon atoms. Additionally, when the alkylene group has a -C(O)N(R) skeleton group... d In the case of (O)-, dialkylmethylenesilyl or divalent organopolysiloxane residues, it is preferred that they are between carbon atoms or with (O). u4 These groups are located at the end of the bonded side.

[0267] 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 11 or 2 to 6. For example, 2, 3, 8, 9, and 11 are examples. In addition, the number of carbon atoms mentioned above can be 1 to 11.

[0268] u4 is either 0 or 1.

[0269] As - (O) u4 -Q b4 From the perspective of ease of compound preparation, -CH2CH2-, -CH2CH2CH2-, and -(CH2) are preferred. b-, -CH2OCH2CH2CH2-, -CH2OCH2CH2CH2CH2CH2-, -OCH2CH2CH2-, -OSi(CH3)2CH2CH2CH2-, -OSi(CH3)2OSi(CH3)2CH2CH2CH2-, -CH2CH2CH2Si(CH3)2PhSi(CH3)2CH2CH2- (where the right side is bonded to Si). b is an integer from 4 to 11.

[0270] w1 is an integer from 0 to 2, preferably 0 or 1, and more preferably 0.

[0271] When there are more than 2 [-(O)] u4 -Q b4 -Si(R) n L 3-n In the case of ], more than 2 [-(O) u4 -Q b4 -Si(R) n L 3-n They can be the same or different.

[0272] R 31 When there are two or more, the two or more (-R) 31 They can be the same or different.

[0273] As a group (3-1A-4) [-[Q e ] s4 -Q a4 -(O) t4 -C[-(O) u4 -Q b4 -Si(R) n L 3-n ] 3-w1 (-R) 31 ) w1 For example, the following groups can be listed. In the following formula, To be with L 3 The bonding positions.

[0274] [Chemistry 13]

[0275]

[0276] [Chemistry 14]

[0277]

[0278] In group (3-1A-5), Q a5 It can be an alkylene group that optionally has an ether-like oxygen atom.

[0279] 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.

[0280] As Q a5 From the perspective of ease of compound preparation, -OCH2CH2CH2-, -OCH2CH2OCH2CH2CH2-, -CH2CH2- or -CH2CH2CH2- (where the right side is bonded to Si).

[0281] Q b5 A group that is an alkylene group, or an alkylene group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms.

[0282] Q b5 The alkylene group shown 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. For example, 2, 3, 8, 9, and 11 are listed. In addition, the number of carbon atoms mentioned above can be 1 to 10.

[0283] Q b5 The number of carbon atoms in the alkylene group having an etheric oxygen atom or a divalent organopolysiloxane residue between carbon atoms is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0284] As Q b5 From the perspective of ease of compound preparation, -CH2CH2CH2- and -CH2CH2OCH2CH2CH2- are preferred (where the right side is related to Si(R)). n L 3-n (bonding).

[0285] 3 [-Q] b5 -Si(R) n L 3-n They can be the same or different.

[0286] [-Q] in group (3-1A-5 a5 -Si[-Q b5 -Si(R) n L 3-n ]3], for example, the following groups can be listed. In the following formula, To be with L 3 The bonding positions.

[0287] [Chemistry 15]

[0288]

[0289] [Chemistry 16]

[0290]

[0291] Q in group (3-1A-6) e The definition is as defined in the group (3-1A-4) above.

[0292] v is 0 or 1.

[0293] Q a6 It can be an alkylene group that optionally has an ether-like oxygen atom.

[0294] 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.

[0295] As Q a6 From the perspective of ease of compound preparation, -CH2OCH2CH2CH2-, -CH2OCH2CH2OCH2CH2CH2-, -CH2CH2-, or -CH2CH2CH2- (wherein, the right side is related to Z) are preferred. a (bonding).

[0296] Z a It is an organopolysiloxane residue with a (w2+1) valence, or a group with an alkylene group having a (w2+1) valence between organopolysiloxane residues.

[0297] w2 is an integer between 2 and 7.

[0298] Examples of (w2+1) valence organopolysiloxane residues and (w2+1) valence groups having an alkylene group between organopolysiloxane residues include the following groups. Wherein, R in the following formula... a As stated above. This indicates the bonding location.

[0299] [Chemistry 17]

[0300]

[0301] Q b6 A group that is an alkylene group, or an alkylene group having an ether oxygen atom or a divalent organopolysiloxane residue between carbon atoms.

[0302] Q b6 The alkylene group shown 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. For example, 2, 3, 8, 9, and 11 are listed. In addition, the number of carbon atoms mentioned above can be 1 to 10.

[0303] Q b6The number of carbon atoms in the alkylene group having an etheric oxygen atom or a divalent organopolysiloxane residue between carbon atoms is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.

[0304] As Q b6 From the perspective of ease of compound production, -CH2CH2- and -CH2CH2CH2- are preferred.

[0305] w2 of [-Q] b6 -Si(R) n L 3-n They can be the same or different.

[0306] As a group (3-1A-6) [-[Q e ] v -Q a6 -Z a [-Q b6 -Si(R) n L 3-n ] w2 For example, the following groups can be listed. In the following formula, To be with L 3 The bonding positions.

[0307] [Chemistry 18]

[0308]

[0309] In group (3-1A-7), Z c Hydrocarbon groups with a valence of (w3+w4+1).

[0310] w3 is an integer greater than or equal to 4.

[0311] w4 is an integer greater than or equal to 0.

[0312] 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).

[0313] 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.

[0314] 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.

[0315] Z cThe number of carbon atoms is preferably 3 to 50, more preferably 4 to 40, and even more preferably 5 to 30.

[0316] w3 is preferably 4~20, more preferably 4~16, even more preferably 4~8, and particularly preferably 4~5.

[0317] w4 is preferably 0~10, more preferably 0~8, further preferably 0~6, particularly preferably 0~3, and most preferably 0~1.

[0318] When there are more than 2 [- (OQ) b4 ) u4 -Si(R) n L 3-n In the case of ], more than 2 [- (OQ) b4 ) u4 -Si(R) n L 3-n They can be the same or different.

[0319] As a functional group (3-1A-7), the following functional groups can be listed as examples. In the following formula, To be with L 3 The bonding positions.

[0320] [Chemistry 19]

[0321]

[0322] In formula (1-1), A can be a group (g2-1) (where d1+d3=1, q=d2+d4), a group (g2-2) (where q=e2), a group (g2-3) (where q=2), a group (g2-4) (where q=h2), a group (g2-5) (where q=i2), a group (g2-6) (where q=1), or a group (g2-7) (where q=1+i3).

[0323] Wherein, A is preferably a group (g2-2) or a group (g2-6).

[0324] [Chemistry 20]

[0325]

[0326] -L 3 -A 1 -Q 12 -C(R) e2 ) 3-e2 (-Q) 22 -) e2 …(g2-2)

[0327] -L 3 -A1 -Q 13 -N(-Q 23 -)2 …(g2-3)

[0328] -L 3 -A 1 -Q 14 -Z 1 (-Q) 24 -) h2 …(g2-4)

[0329] -L 3 -A 1 -Q 15 -Si(R) e3 ) 3-i2 (-Q) 25 -) i2 …(g2-5)

[0330] -L 3 -A 1 -Q 26 - …(g2-6)

[0331] -L 3 -A 1 -Q 12 -CH (-Q) 22 -)-Si(R e3 ) 3-i3 (-Q) 25 -) i3 …(g2-7)

[0332] In equations (g2-1) to (g2-7), L 3 Side and L 2 Bonding, Q 22 Q 23 Q 24 Q 25 Or Q 26 Side and [-Si(R)] n L 3-n ] Bonding.

[0333] L 3 The definition is as described above.

[0334] A 1 For single bond, -C(O)NR 6 -, -C(O)-, -OC(O)O-, -NHC(O)O-, -NHC(O)NR 6 -、-O- or -SO2NR 6 -

[0335] Q 11It is a single bond, -O-, alkylene, or an alkylene group having -C(O)NR between carbon atoms. 6 -、-C(O)-、-NR 6 - or -O- groups.

[0336] 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, where A has more than 2 Qs 12 At that time, more than 2 Qs 12 They can be the same or different.

[0337] Q 13 It is a single bond (where A is a single bond). 1 -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 with - or -O-, or a group having -C(O)- at the N-side end of an alkylene group.

[0338] In Q 14 The bonded Z 1 Q is a carbon atom in the case of 14 For Q 12 In Q 14 The bonded Z 1 Q is a nitrogen atom in the case of 14 For Q 13 In A 2 Having more than 2 Qs 14 At that time, more than 2 Qs 14 They can be the same or different.

[0339] 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, where A has more than 2 Qs 15 At that time, more than 2 Qs 15 They can be the same or different.

[0340] Q 22 Alkylenes, wherein the carbon atoms of alkylenes having two or more carbon atoms have a -C(O)NR bond. 6 -、-C(O)-、-NR 6- or -O- groups, alkyl groups with -C(O)NR at the end of the side not connected to Si. 6 -、-C(O)-、-NR 6 A group with - or -O-, or an alkylene group having -C(O)NR between carbon atoms. 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, where A has more than 2 Qs 22 At that time, more than 2 Qs 22 They can be the same or different.

[0341] Q 23 It is an alkylene group, or an alkylene group having -C(O)NR between carbon atoms. 6 -、-C(O)-、-NR 6 - or -O- groups, 2 Qs 23 They can be the same or different.

[0342] In Q 24 The bonded Z 1 When the atom in Q is a carbon atom, 24 For Q 22 In Q 24 The bonded Z 1 When the atom in Q is a nitrogen atom, 24 For Q 23 In A, there are more than two Qs. 24 In the case of 2 or more Q 24 They can be the same or different.

[0343] 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, where A has more than 2 Qs 25 At that time, more than 2 Qs 25 They can be the same or different.

[0344] Q 26 It is an alkylene group, or an alkylene group having -C(O)NR between carbon atoms. 6 -、-C(O)-、-NR 6 - or -O- groups.

[0345] Q 22 Q23 Q 24 Q 25 Q 26 When it is an alkylene group, the number of carbon atoms is preferably 1 to 60, more preferably 1 to 30. It can be 1 to 20, 1 to 10, or 1 to 6.

[0346] Z 1 A group having a (1+h2) valence and a ring structure, the group having Q 14 Directly bonded carbon or nitrogen atoms, and possessing Q 24 Directly bonded carbon or nitrogen atoms.

[0347] R e1 It consists of hydrogen atoms or alkyl groups, and more than two R atoms. e1 They can be the same or different.

[0348] R e2 It can be a hydrogen atom, hydroxyl group, alkyl group or acyloxy group.

[0349] 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.

[0350] d1 is 0 or 1. d3 is 0 or 1. In addition, d1 + d3 is 1.

[0351] d2 is an integer from 0 to 3. d4 is an integer from 0 to 3. Additionally, d2+d4 is an integer from 1 to 5.

[0352] d1+d2 are integers from 1 to 3.

[0353] d3+d4 is an integer from 1 to 3.

[0354] e2 is 2 or 3.

[0355] h2 is an integer greater than or equal to 1, preferably 2 or 3.

[0356] i2 is an integer from 1 to 3, preferably 2 or 3.

[0357] i3 is 2 or 3.

[0358] From the perspectives of ease of compound manufacturing and superior wear resistance of the surface treatment layer, Q 11 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 also have 2 to 10 or 2 to 6 carbon atoms. 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.

[0359] As Z 1 The ring structures in the text can be exemplified by the ring structures described above, and the preferred method is also the same. It should be noted that, due to Q... 14 Q 24 Direct bonding at Z 1 Therefore, for example, it would not be an alkylene group connected to the ring structure, Q 14 Q 24 The case of further connection with the alkylene group.

[0360] 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.

[0361] 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.

[0362] As for h2, from the perspective of ease of compound manufacturing and superior wear resistance of the surface treatment layer, 2 to 6 are preferred, 2 to 4 are more preferred, and 2 or 3 are even more preferred.

[0363] Other forms of A can be listed as group (g2-8) (where d1+d3=1, q=d2×k3+d4×k3), group (g2-9) (where q=e2×k3), group (g2-10) (where q=2×k3), group (g2-11) (where q=h2×k3), group (g2-12) (where q=i2×k3), group (g2-13) (where q=k3), or group (g2-14) (where q=i3×k3+k3).

[0364] [Chemistry 21]

[0365]

[0366] -L 3 -A 1 -Q 12 -C(R) e2 ) 3-e2 (-Q)22 -G 1 ) e2 …(g2-9)

[0367] -L 3 -A 1 -Q 13 -N(-Q 23 -G 1 )2 …(g2-10)

[0368] -L 3 -A 1 -Q 14 -Z 1 (-Q) 24 -G 1 ) h2 …(g2-11)

[0369] -L 3 -A 1 -Q 15 -Si(R) e3 ) 3-i2 (-Q) 25 -G 1 ) i2 …(g2-12)

[0370] -L 3 -A 1 -Q 26 -G 1 …(g2-13)

[0371] -L 3 -A 1 -Q 12 -CH (-Q) 22 -G 1 )-Si(R e3 ) 3-i3 (-Q) 25 -G 1 ) i3 …(g2-14)

[0372] In equations (g2-8) to (g2-14), L 3 Side and L 2 Bonding, G 1 Side and [-Si(R)] n L 3-n ] Bonding.

[0373] G 1 For the following groups (g3), A has two or more Gs. 1 They can be the same or different. G 1The symbols other than those in equations (g2-1) to (g2-7) are the same.

[0374] -Si(R) 8 ) 3-k3 (-Q) 3 -) k3 …(g3)

[0375] In group (g3), the Si side is related to Q. 22 Q 23 Q 24 Q 25 and Q 26 Connection, Q 3 Side and [-Si(R)] n L 3-n [Connection. R] 8 It is an alkyl group. Q 3 Alkylenes, wherein the 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.

[0376] From the perspectives of ease of compound manufacturing and 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 also have 2 to 10 or 2 to 6 carbon atoms. 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.

[0377] From the perspective of ease of compound production, R 8 The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3, and even more preferably 1 to 2.

[0378] 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.

[0379] 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 even more preferably 1 to 2.

[0380] p is preferably 0 or 1.

[0381] Examples of compounds according to the present invention include compounds with the following formula. From the perspectives of ease of industrial manufacture, ease of processing, and superior water repellency and abrasion resistance of the surface treatment layer, compounds with the following formula are preferred. The R in the compound with the following formula... t Compared with the above [TO-(Si(R)] 2 )2-O) ma -Si(R) 2 )2-L 1 -L 2 -L 3 The same applies to both, and the preferred method is also the same.

[0382] For example, compounds in formula (1-1) where A is a group (g2-1) can be listed as follows.

[0383] [Chemistry 22]

[0384]

[0385] For compounds in formula (1-1) where A is a group (g2-2), examples include the following compounds. In the following formula, Ak refers to an alkyl group (e.g., an alkyl group with 1 to 15 carbon atoms).

[0386] [Chemistry 23]

[0387]

[0388] [Chemistry 24]

[0389]

[0390] [Chemistry 25]

[0391]

[0392] [Chemistry 26]

[0393]

[0394] For example, compounds in formula (1-1) where A is a group (g2-3) can be listed as follows.

[0395] [Chemistry 27]

[0396]

[0397] For example, compounds in formula (1-1) where A is a group (g2-4) can be listed as follows.

[0398] [Chemistry 28]

[0399]

[0400] For example, compounds in formula (1-1) where A is a group (g2-5) can be listed as follows.

[0401] [Chemistry 29]

[0402]

[0403] For example, compounds in formula (1-1) where A is a group (g2-6) can be listed as follows.

[0404] [Chemistry 30]

[0405]

[0406] As compounds in formula (1-1) where A is a group (g2-7), examples of compounds with the following formulas can be listed.

[0407] [Chemistry 31]

[0408]

[0409] As compounds in formula (1-1) where A is a group (g2-8), examples of compounds with the following formulas can be listed.

[0410] [Chemistry 32]

[0411]

[0412] For example, compounds in formula (1-1) where A is a group (g2-9) can be listed as follows.

[0413] [Chemistry 33]

[0414]

[0415] As compounds in formula (1-1) where A is a group (g2-10), examples of compounds with the following formulas can be listed.

[0416] [Chemistry 34]

[0417]

[0418] [Chemistry 35]

[0419]

[0420] As compounds in formula (1-1) where A is a group (g2-11), examples of compounds with the following formulas can be listed.

[0421] [Chemistry 36]

[0422]

[0423] For example, compounds in formula (1-1) where A is a group (g2-12) can be listed as follows.

[0424] [Chemistry 37]

[0425]

[0426] As compounds in formula (1-1) where A is a group (g2-13), examples of compounds with the following formulas can be listed.

[0427] [Chemistry 38]

[0428]

[0429] As compounds in formula (1-1) where A is a group (g2-14), examples of compounds with the following formulas can be listed.

[0430] [Chemistry 39]

[0431]

[0432] As a compound represented by formula (1-1), the following compounds can be listed for example. The definition of ma is as described above.

[0433] [Chemistry 40]

[0434]

[0435] [Chemistry 41]

[0436]

[0437] [Chemistry 42]

[0438]

[0439] Alternatively, as a compound (1-1), it could be L 1 Alkylene, L 2 For -CH=CH-, -C≡C- or -C(=CH2)-, L 3 Compounds that are alkylene groups. L 1 and L 3The alkylene groups can be linear or branched, but are preferably linear. 1 and L 3 The preferred number of carbon atoms is 1 to 30, but can be 1 to 25, 1 to 20, 1 to 10, or 5 to 10. For example, it can be L... 1 and L 3 Alkylenes with 1 to 10 or 5 to 10 carbon atoms, L 2 The preferred range and combination can be a combination of -CH=CH-, -C≡C-, or -C(=CH2)-. It should be noted that the compounds included in the above preferred range and combination can have a q of 1.

[0440] <Compounds shown in formula (1-2)>

[0441] (L) 3-n (R) n Si) q -AL 2 -L 1 -(Si(R) 2 )2-O) mb -Si(R) 2 )2-L 1 -L 2 -A-(Si(R)) n L 3-n ) q (1-2)

[0442] In equation (1-2),

[0443] R 2 Each is an independent hydrocarbon group.

[0444] L 1 It is a single bond or a divalent linker.

[0445] L 2 For -CH=CH-, -C≡C-, or -C(=CH2)-,

[0446] A is a single bond or a (q+1) valence linker.

[0447] R are each an independent hydrocarbon group.

[0448] L can be a hydrolyzable group, a group with a hydrolyzable group, or a hydroxyl group, each independently.

[0449] mb is a number greater than or equal to 0.

[0450] n are independent integers from 0 to 2.

[0451] Each q is an integer greater than or equal to 1.

[0452] Each group in formula (1-2) has the same meaning as each group in formula (1-1), and the preferred method is also the same.

[0453] In equation (1-2), mb is a number greater than or equal to 0.

[0454] ma is preferably a number from 2 to 600, more preferably a number from 3 to 500, even more preferably a number from 9 to 50, particularly preferably a number from 11 to 30, and most preferably a number from 11 to 25.

[0455] Additionally, as compounds (1-2), it could be L 1 Alkylene, L 2 For -CH=CH-, -C≡C- or -C(=CH2)-, L 3 Compounds that are alkylene groups. L 1 and L 3 The alkylene groups can be linear or branched, but are preferably linear. 1 and L 3 The preferred number of carbon atoms is 1 to 30, but can be 1 to 25, 1 to 20, 1 to 10, or 5 to 10. For example, it can be L... 1 and L 3 Alkylenes with 1 to 10 or 5 to 10 carbon atoms, L 2 The preferred range and combination can be a combination of -CH=CH-, -C≡C-, or -C(=CH2)-. It should be noted that the compounds included in the above preferred range and combination can have a q of 1.

[0456] The number-average molecular weight (Mn) of the compounds of the present invention is preferably 500 to 20,000, more preferably 600 to 18,000, and even more preferably 700 to 15,000.

[0457] 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.

[0458] [Composition]

[0459] The compositions of the present invention may contain only the compounds of the present invention, and there are no particular limitations on other components besides the compounds of the present invention.

[0460] That is, the composition of the present invention only needs to contain at least one of the compounds shown in formula (1-1) and the compounds shown in formula (1-2). Alternatively, the composition of the present invention may contain both the compounds shown in formula (1-1) and the compounds shown in formula (1-2).

[0461] The compositions of the present invention preferably contain the compounds of the present invention and contain a liquid medium. When a liquid medium is included, the compositions of the present invention may be in a liquid state, and may be a solution or a dispersion.

[0462] The composition of the present invention may contain only the compounds of the present invention, or it may contain impurities such as byproducts generated during the manufacturing process of the compounds of the present invention.

[0463] The content of the compound of the present invention relative to the total amount of the composition of the present invention 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. When the composition of the present invention is used in a wet coating method, the content of the compound of the present invention relative to the total amount of the composition of the present invention is preferably 0.01 to 10% by mass, more preferably 0.02 to 5% by mass, even more preferably 0.03 to 3% by mass, and particularly preferably 0.05 to 2% by mass.

[0464] The liquid medium contained in the composition of the present invention may be only one type or may be two or more types.

[0465] Organic solvents are preferred as liquid media.

[0466] Organic solvents can be categorized as compounds composed solely of hydrogen and carbon atoms, or compounds composed solely of hydrogen, carbon, and oxygen atoms. Specifically, they can be categorized as hydrocarbon-based organic solvents, ketone-based organic solvents, ether-based organic solvents, ester-based organic solvents, glycol-based organic solvents, and alcohol-based organic solvents. Among these, hydrocarbon-based organic solvents or ester-based organic solvents are preferred.

[0467] Specific examples of hydrocarbon-based organic solvents include pentane, hexane, heptane, octane, hexadecane, isohexane, isooctane, isononane, cycloheptane, cyclohexane, bicyclohexane, benzene, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, n-butylbenzene, sec-butylbenzene, and tert-butylbenzene.

[0468] 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.

[0469] Specific examples of ether-based organic solvents include diethyl ether, cyclopentylmethyl ether, tetrahydrofuran, and 1,4-dioxane.

[0470] 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 ether acetate, propylene glycol dimethyl acetate, ethylene glycol monoethyl ether acetate, and ethylene glycol monomethyl ether acetate. 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, propylene glycol diacetate, dipropylene glycol methyl ether acetate, 1,3-butanediol diacetate, 1,4-butanediol diacetate, 1,3-butanediol diacetate, 1,6-hexanediol diacetate, γ-butyrolactone, triacetin, and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate.

[0471] 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 ether, and dipropylene glycol. Monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, 1,3-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 and polyethylene glycol dimethyl ether.

[0472] 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 glycol, octanediol, 2,4-diethylpentanediol, butylethylpropanediol, 2-methyl-1,3-propanediol, 4-hydroxy-4-methyl-2-pentanone, 2-ethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, isodecanol, isothietol, 3-methoxy-3-methyl-1-butanol, 2-methoxybutanol, 3-methoxybutanol, cyclohexanol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, and methylcyclohexanol.

[0473] In addition, examples of organic solvents include halogenated organic solvents, fluorinated organic solvents, nitrogen-containing compounds, sulfur-containing compounds, and siloxane compounds other than the compounds of this invention.

[0474] 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.

[0475] Examples of fluorinated organic solvents include polyfluoroaromatic hydrocarbons (e.g., 1,3-bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C6F...). 13 CH2CH3 (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); 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., Novec 7200 manufactured by Sumitomo 3M Corporation), perfluorohexyl methyl ether (C2F5CF(OC)). Alkyl perfluoroalkyl ethers (perfluoroalkyl and alkyl can be straight-chain or branched), such as H3)C3F7) (e.g. Novec (trademark) 7300 manufactured by Sumitomo 3M Co., Ltd.), and CF3CH2OCF2CHF2 (e.g. ASAHIKLIN (registered trademark) AE-3000 manufactured by AGC Co., Ltd.); hydrofluoroolefins (HFO) (e.g. 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd) (e.g. AMOLEA (Japanese: アモレア) (registered trademark) AS-300 manufactured by AGC Co., Ltd.).

[0476] Examples of nitrogen-containing compounds include nitrobenzene, acetonitrile, benzonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,3-dimethyl-2-imidazolinone.

[0477] Examples of sulfur-containing compounds include carbon disulfide and dimethyl sulfoxide.

[0478] Examples of siloxane compounds other than those of the present invention include hexamethyldisiloxane, hexaethyldisiloxane, octamethyltrisiloxane, octaethyltrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, octamethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, and decamethyltetrasiloxane.

[0479] The content of the liquid medium relative to the total amount of the composition of the present invention 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 of the present invention used in a wet coating method, the content of the liquid medium relative to the total amount of the composition of the present invention is preferably 90 to 99.99% by mass, more preferably 95 to 99.98% by mass, even more preferably 97 to 99.97% by mass, and particularly preferably 98 to 99.95% by mass.

[0480] In addition to the compounds and liquid media of the present invention, the compositions of the present invention may contain other components without impairing the effects of the present invention.

[0481] Other components include additives, specifically catalysts such as acid catalysts and base catalysts that promote the hydrolysis and condensation reactions of reactive silyl groups.

[0482] As catalysts, for example, any suitable acid or base, transition metal (e.g., Ti, Ni, Sn, Zr, Al, B), sulfur-containing compounds with non-shared electron pairs 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.

[0483] 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.

[0484] In addition, examples of alkaline catalysts include ammonia, sodium hydroxide, potassium hydroxide, and organic amines such as triethylamine and diethylamine.

[0485] In addition, other components may include metal compounds having hydrolyzable groups (hereinafter also referred to as "specific metal compounds"). If the composition of the present invention contains a specific metal compound, the sliding properties and antifouling properties of the surface treatment layer can be further improved. Specific metal compounds may include metal compounds represented by any one of formulas (M1) to (M3).

[0486] M(X) b1 ) m1 (X) b2 ) m2 (X) b3 ) m3 …(M1)

[0487] Si(X) b4 (X) b5 3 … (M2)

[0488] (X) b6 )3Si-(Y b1 )-Si(X b7 3 … (M3)

[0489] In formula (M1),

[0490] M is a trivalent or tetravalent metal atom.

[0491] X b1 Each is an independent hydrolyzable group.

[0492] X b2 Each is an independent group containing a siloxane backbone.

[0493] X b3 Each is an independent group containing a hydrocarbon chain.

[0494] m1 is an integer between 2 and 4.

[0495] m2 and m3 are each independent integers from 0 to 2.

[0496] When M is a trivalent metal atom, m1+m2+m3 is 3; when M is a tetravalent metal atom, m1+m2+m3 is 4.

[0497] In formula (M2),

[0498] X b4 It consists of hydrolyzable silane oligomer residues.

[0499] X b5 Each is independently a hydrolyzable group or an alkyl group having 1 to 4 carbon atoms.

[0500] In formula (M3),

[0501] Xb6 and X b7 Each is independently a hydrolyzable group or a hydroxyl group.

[0502] Y b1 It is a divalent organic group.

[0503] In formula (M1), the metal represented by M also includes half-metals such as Si and Ge. As M, trivalent metals and tetravalent metals are preferred, Al, Fe, In, Hf, Si, Ti, Sn or Zr are more preferred, Al, Si, Ti or Zr are even more preferred, and Si is particularly preferred.

[0504] In equation (M1), X is... b1 The hydrolytic group shown has the same meaning as the hydrolytic group represented by L in the above formula (1-1), and the preferred method is also the same.

[0505] X b2 The shown group containing a siloxane skeleton has a siloxane unit (-Si-O-), which can be either linear or branched. As the siloxane unit, dialkylsiloxy is preferred, and examples include dimethylsiloxy and diethylsiloxy. The number of repetitions of the siloxane unit in the group containing the siloxane skeleton is 1 or more, preferably 1 to 5, more preferably 1 to 4, and even more preferably 1 to 3.

[0506] 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.

[0507] Hydrolyzable groups, hydrocarbon groups (preferably alkyl groups), etc., can be bonded to the silicon atoms at the ends of groups containing siloxane skeletons.

[0508] The number of elements containing the siloxane skeleton is preferably 100 or less, more preferably 50 or less, and even more preferably 30 or less. The upper limit of the number of elements is preferably 10 or more.

[0509] As a group containing a siloxane backbone, it is preferably composed of -(O-Si(CH3)2) n CH3 represents the group, where n is an integer from 1 to 5. This indicates the bonding site with adjacent atoms.

[0510] X b3The hydrocarbon-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 or branched, preferably straight. The hydrocarbon chain can be saturated or unsaturated, preferably saturated. The number of carbon atoms in the hydrocarbon-containing group is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. As the hydrocarbon-containing group, alkyl is preferred, more preferably methyl, ethyl, or propyl.

[0511] m1 is preferably 3 or 4.

[0512] As the compound represented by formula (M1), it is preferred to be a compound represented by any one of formulas (M1-1) to (M1-5) where M is Si, and more preferably a compound represented by formula (M1-1). As the compound represented by formula (M1-1), it is preferred to be tetraethoxysilane, tetramethoxysilane, or triethoxymethylsilane.

[0513] Si(X) b1 4 … (M1-1)

[0514] CH3-Si(X) b1 3 … (M1-2)

[0515] C2H5-Si(X) b1 3 … (M1-3)

[0516] n-C3H7-Si(X) b1 3 … (M1-4)

[0517] (CH3)2CH-Si(X) b1 3 … (M1-5)

[0518] In formula (M2), X b4 The number of silicon atoms contained in the hydrolyzable silane oligomer residues shown is preferably 3 or more, more preferably 5 or more, and even more preferably 7 or more. The number of silicon atoms is preferably 15 or less, more preferably 13 or less, and even more preferably 10 or less.

[0519] The hydrolyzable silane oligomer residues may have alkoxy groups bonded to silicon atoms. Examples of such alkoxy groups include methoxy, ethoxy, propoxy, and butoxy, with methoxy or ethoxy being preferred. The hydrolyzable silane oligomer residues may have one or more of these alkoxy groups, with one being preferred.

[0520] Examples of hydrolyzable silane oligomer residues include (C2H5O)3Si-(OSi(OC2H5)2)4O- Wait. Here, This indicates the bonding site with adjacent atoms.

[0521] In equation (M2), X is... b5 The hydrolyzable group shown may include the same group, cyano group, hydrogen atom, and allyl group as the hydrolyzable group shown by L in the above formula (1-1), preferably an alkoxy group or an isocyanate group. As an alkoxy group, it is preferably an alkoxy group with 1 to 4 carbon atoms.

[0522] As X b5 Preferably, hydrolyzable groups are used.

[0523] Examples of compounds represented by formula (M2) include (H5C2O)3-Si-(OSi(OC2H5)2)4OC2H5, etc.

[0524] The compound represented by formula (M3) is a compound with reactive silyl groups at both ends of a divalent organic group, namely a bissilane.

[0525] In formula (M3), X is used as b6 and X b7 The hydrolyzable groups shown may include alkoxy, acyloxy, ketoxime, alkenoxy, amino, aminooxy, amide, isocyanate, and halogen atoms, with alkoxy or isocyanate groups being preferred. As an alkoxy group, an alkoxy group with 1 to 4 carbon atoms is preferred, and methoxy or ethoxy groups are more preferred.

[0526] In formula (M3), X b6 and X b7 They can be the same group or different group. From the point of view of easy access, X b6 and X b7 Preferably, the groups are the same as each other.

[0527] In formula (M3), Y b1 The Y-type is a divalent organic group consisting of reactive silyl groups at both ends. b1 The number of carbon atoms is preferably 1 to 8, more preferably 1 to 3.

[0528] As Y b1 Examples include alkylene, phenylene, and alkylene with an ether-like oxygen atom between carbon atoms. For example, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2CH2-, -CH2C(CH3)2CH2-, -C(CH3)2CH2CH2C(CH3)2-, -CH2CH2OCH2CH2-, -CH2CH2CH2OCH2CH2CH2-, -CH(CH3)CH2OCH2CH(CH3)-, and -C6H4-.

[0529] 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.

[0530] The content of other components that may be included in the composition of the present invention is preferably 10% by mass or less, more preferably 1% by mass or less, relative to the total amount of the composition of the present invention. When the composition of the present invention contains a specific metal compound, the content of the specific metal compound relative to the total amount of the composition of the present invention 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.

[0531] The total content of the compound of the present invention and other components (hereinafter also referred to as "solid component concentration") relative to the total amount of the composition of the present invention 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 component concentration of the composition of the present invention is a value calculated from the mass of the composition before heating and the mass after heating in a convection dryer at 120°C for 4 hours.

[0532] The compositions of the present invention contain a liquid medium, and are therefore useful for coating purposes, and can be used as coating liquids.

[0533] In addition to the compounds and liquid media of the present invention, the compositions of the present invention may also contain other components besides the compounds and liquid media of the present invention, without impairing the effects of the present invention. Examples of such other components include, for instance, known additives such as acid catalysts and / or basic catalysts that promote the hydrolysis and condensation reactions of hydrolyzable silyl groups.

[0534] The content of other components in this surface treatment agent is preferably 10% by mass or less, more preferably 1% by mass or less.

[0535] Other components may include compounds represented by formula (2).

[0536] [Y 1 3Y 2 -(O) s1 -Y 3 ] s2 Y 4 (Si(Y) 5 ) s3 (Y) 6 ) 3-s3) s4 …(2)

[0537] In equation (2), Y 1 Each is independently a hydrocarbon group or a trialkylsilyloxy group.

[0538] Y 2 It is Si, Sn or Ge,

[0539] s1 is 0 or 1.

[0540] Y 3 Each is independently an alkylene chain or a polyepoxide chain, or a combination of an alkylene chain and divalent polysiloxane residues.

[0541] Y 4 It is a linking group with a single bond or a s²+s⁴ valence.

[0542] Y 5 Each is an independent hydrocarbon group.

[0543] Y 6 Each is independently a hydrolyzable group or a hydroxyl group.

[0544] Each s3 is an independent integer from 0 to 2.

[0545] s2 and s4 are each independent integers greater than or equal to 1.

[0546] Among them, Y 4 It does not contain -CH=CH-, -C≡C-, or -C(=CH2)-.

[0547] Y is preferred as compound (2). 3 Compounds with alkylene chains or polyepoxide chains.

[0548] Specific examples of compound (2) include the following compounds. In the formula, α is preferably 9 to 50, more preferably 11 to 30, and particularly preferably 11 to 25.

[0549] [Chemistry 43]

[0550]

[0551] When the other component in this surface treatment agent is compound (2), the content of compound (2) is preferably 50% by mass or less, more preferably 40% by mass or less.

[0552] [Surface treatment agent]

[0553] In one embodiment, the surface treatment agent of the present invention comprises the compound of the present invention. Alternatively, the surface treatment agent of the present invention may comprise the compound of the present invention and a liquid medium. The surface treatment agent of the present invention may be a composition of the present invention. The preferred embodiment of the liquid medium in the surface treatment agent of the present invention is the same as the preferred embodiment of the liquid medium in the composition of the present invention.

[0554] The surface treatment agent of the present invention may contain at least one of the compounds shown in formula (1-1) and formula (1-2). Alternatively, the surface treatment agent of the present invention may contain both the compound shown in formula (1-1) and the compound shown in formula (1-2).

[0555] [thing]

[0556] In one embodiment, the article of the present invention comprises a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent of the present invention.

[0557] The surface treatment layer can be formed on a portion of the substrate surface or on the entire substrate surface. The surface treatment layer can be spread into a film on the substrate surface or distributed in a dotted pattern.

[0558] In the surface treatment layer, the compound of the present invention is contained in a state in which part or all of the reactive silyl group has been hydrolyzed and the silanol group has undergone a dehydration condensation reaction.

[0559] 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 effects brought by 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 using a thin film analysis X-ray diffractometer (product name "ATX-G", manufactured by RIGAKU) and by obtaining the interference pattern of reflected X-rays through the X-ray reflectivity method, and then calculating the thickness from the vibration period of the interference pattern.

[0560] There is no particular limitation 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 when other articles (e.g., styluses) or human fingers come into contact with them; substrates that are sometimes held by human fingers during operation; and substrates that are sometimes placed on other articles (e.g., a platform).

[0561] 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.

[0562] Examples of substrates include building materials, decorative building materials, interior furnishings, transportation equipment (e.g., automobiles), billboards, signs, drinking utensils, 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 outer casing (excluding the display) of devices such as mobile phones (e.g., smartphones), portable information terminals, game consoles, and remote controls. The substrate can be in sheet or film form.

[0563] 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.

[0564] 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.

[0565] 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 article of the present invention preferably comprises 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 the present invention.

[0566] The substrate layer is preferably a layer containing an oxide of 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.

[0567] The Group 1 elements of the periodic table (hereinafter also referred to as "Group 1 elements") refer to lithium, sodium, potassium, rubidium, and cesium. From the viewpoint of enabling the surface treatment layer to be formed more uniformly and without defects on the substrate layer, or from the viewpoint of further suppressing deviations in the composition of 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.

[0568] The Group 2 elements of the periodic table (hereinafter also referred to as "Group 2 elements") refer to beryllium, magnesium, calcium, strontium, and barium. From the viewpoint of enabling the surface treatment layer to be formed more uniformly and without defects on the substrate layer, or from the viewpoint of further suppressing deviations in the composition of 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.

[0569] The Group 4 elements of the periodic table (hereinafter also referred to as "Group 4 elements") refer to titanium, zirconium, and hafnium. From the viewpoint of enabling the surface treatment layer to be formed more uniformly and without defects on the substrate layer, or from the viewpoint of further suppressing deviations in the composition of 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.

[0570] 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-treated layers. The base layer may contain two or more Group 5 elements.

[0571] The elements in Group 13 of the periodic table (hereinafter also referred to as "Group 13 elements") refer to boron, aluminum, gallium, and indium. From the viewpoint of enabling the surface treatment layer to be formed more uniformly and without defects on the substrate layer, or from the viewpoint of further suppressing deviations in the composition of the substrate layer between samples, boron, aluminum, and gallium are preferred as Group 13 elements, and boron and aluminum are more preferred. The substrate layer may contain two or more Group 13 elements.

[0572] The elements in Group 15 of the periodic table (hereinafter also referred to as "Group 15 elements") refer to nitrogen, phosphorus, arsenic, antimony, and bismuth. From the viewpoint of enabling the surface treatment layer to be formed more uniformly and without defects on the substrate layer, or from the viewpoint of further suppressing deviations in the composition of 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.

[0573] As specific elements contained in the base layer, Group I elements, Group II elements, and Group XIII elements are preferred because the surface treatment layer has better wear resistance. Group I elements and Group II elements are more preferred, and Group I elements are even more preferred.

[0574] As a specific element, it can contain only one type of element or two or more types of elements.

[0575] The oxide contained in the substrate layer can be a mixture of oxides of the above-mentioned elements (silicon and specific elements) individually (e.g., a mixture of silicon oxide and oxides of specific elements), a composite oxide containing two or more of the above-mentioned elements, or a mixture of oxides of the above-mentioned elements individually and composite oxides.

[0576] 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.

[0577] 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.

[0578] The base layer can be a single layer or multiple layers. The base layer can also have uneven surfaces.

[0579] 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 substrate layer to the surface treatment 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.

[0580] The thickness of the basal layer was determined by cross-sectional observation of the basal layer based on transmission electron microscopy (TEM).

[0581] The substrate layer can be formed, for example, by vapor deposition using vapor deposition materials or by wet coating.

[0582] The vapor deposition material used in the vapor deposition method preferably contains oxides containing silicon and specific elements.

[0583] 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.

[0584] Here, "molten body" refers to a solid obtained by melting the powder of vapor-deposited material at high temperature and then cooling and solidifying it. "Sintered body" refers to a solid obtained by sintering the powder of vapor-deposited material. Depending on the need, it can also replace the powder of vapor-deposited material by pressing it into a shaped body. "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.

[0585] Vaporized materials can be manufactured, for example, by the following methods.

[0586] • A method of mixing silicon oxide powder with powder of oxides of specific elements to obtain powder of vapor deposition material.

[0587] • 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.

[0588] • A method for obtaining a sintered body by drying a mixture of silicon-containing powder (e.g., powder composed of silicon oxide, silica sand, silica gel) and powder containing a specific element (e.g., powder of oxide of a specific element, carbonate, sulfate, nitrate, oxalate, hydroxide) with water, and then firing the dried mixture or a shaped body formed by pressing it.

[0589] • A method of obtaining a melt by melting a silicon-containing powder (e.g., powder composed of silicon oxide, silica sand, silica gel) with a powder containing a specific element (e.g., powder of oxide of a specific element, carbonate, sulfate, nitrate, oxalate, hydroxide) at a high temperature and then cooling and solidifying the melt.

[0590] As a specific example of a vapor deposition method that uses 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.

[0591] The temperature during vapor deposition (for example, the temperature of the vessel in which the vapor deposition material is placed when using a vacuum vapor deposition apparatus) is preferably 100°C to 3,000°C, and more preferably 500°C to 3,000°C.

[0592] The pressure during vapor deposition (for example, the pressure inside the tank where the vapor deposition material is placed when using a vacuum vapor deposition apparatus) is preferably 1 Pa or less, and more preferably 0.1 Pa or less.

[0593] When using vapor deposition materials to form the base layer, one vapor deposition material can be used, or two or more vapor deposition materials containing different elements can be used.

[0594] 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 the vapor-deposited material is irradiated with an electron beam to directly heat the material, causing its surface to melt and evaporate. From the viewpoint that localized heating is possible, allowing even high-melting-point substances to evaporate, and that the areas not irradiated by the electron beam are at low temperatures, eliminating concerns about reactions with the container or the introduction of impurities, the electron gun method is preferred as an evaporation method.

[0595] Evaporation methods for depositing materials can utilize multiple boats or a single boat containing all the depositing materials. 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 different boats, and alternating deposition in different boats. The deposition conditions and sequence are appropriately selected based on the composition of the substrate.

[0596] In wet coating methods, it is preferable to form a base layer on a substrate by using a coating liquid containing a silicon-containing compound, a compound containing a specific element, and a liquid medium.

[0597] Specific examples of silicon compounds include silicon oxide, silicic acid, partial condensates of silicic acid, alkoxysilanes, and partial hydrolysis condensates of alkoxysilanes.

[0598] 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.

[0599] Examples of liquid media include those identical to those contained in the compositions of the present invention.

[0600] The content of the liquid medium relative to the total amount of the coating liquid used to form the substrate layer is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass.

[0601] Specific examples of wet coating methods used to form a substrate include spin coating, wipe coating, spray coating, scraper coating, dip coating, mold coating, inkjet coating, flow coating, roller coating, tape casting, Langmuir-Blodgett method, and gravure coating.

[0602] Preferably, the coating film is dried after the coating liquid is wet-applied. The drying temperature of the coating film is preferably 20~200°C, more preferably 80~160°C.

[0603] The article of the present invention can be an optical material having a surface treatment layer on the outermost layer.

[0604] As optical materials, in addition to optical materials related to displays, a wide variety of optical materials can be preferred.

[0605] As optical materials, examples include cathode ray tubes (CRTs); such as 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 are applied to their surfaces.

[0606] The articles of the present invention 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 devices, copiers, PCs, displays (e.g., liquid crystal displays, organic EL displays, plasma displays, touch panel displays), touch panels, protective films and anti-reflective films.

[0607] In addition, as optical components, examples include front protective panels, anti-reflective panels, polarizing plates, and anti-glare panels for displays such as PDPs and LCDs; disc surfaces for Blu-ray (Blu-ray, DVD, CD-R, MO, etc.); optical fibers; and the display surfaces of clocks and watches.

[0608] In particular, the articles of the present invention are preferably displays or touch panels.

[0609] The articles of this invention can be medical devices or medical materials. Additionally, the articles of this invention can be automotive interior and exterior components. Examples of exterior components include vehicle windows, lamp covers, and exterior camera covers. Examples of interior components include dashboard covers, navigation system touch panels, and decorative interior materials.

[0610] When the article of the present invention is an optical component, the material constituting the surface of the substrate is a material for optical components, such as glass or transparent plastic. Furthermore, when the article of the present invention 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.

[0611] 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). When fabricating a multilayer antireflective layer, the outermost layer preferably uses SiO2 and / or SiO. 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). Furthermore, the substrate can have insulating layers, adhesive layers, protective layers, decorative frame layers (I-CON), atomizing film layers, hard coating layers, polarizing films, retardation films, and liquid crystal display modules, depending on its specific specifications.

[0612] [How to make the item]

[0613] The method for manufacturing the article of the present invention is, for example, to perform surface treatment on a substrate using the surface treatment agent of the present invention, thereby manufacturing an article on which a surface treatment layer is formed. Examples of surface treatments include dry coating and wet coating.

[0614] 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 compound of the present invention impregnated in porous metals such as iron or steel can be used. Alternatively, granular materials containing the compound of the present invention can be impregnated in porous metals such as iron or steel by impregnating a composition comprising the compound of the present invention and a liquid medium, followed by drying the liquid medium.

[0615] Examples of wet coating methods include spin coating, wipe coating, spray coating, scraper coating, dip coating, mold coating, inkjet coating, flow coating, roller coating, tape casting, Langmuir-Blodgett coating, and gravure coating.

[0616] To improve the wear resistance of the surface treatment layer, operations can be performed as needed to promote the reaction between the compound of the present invention and the substrate. Examples of such operations include heating, humidification, and light irradiation.

[0617] For example, heating a substrate with a surface-treated layer in a humid atmosphere can promote reactions such as hydrolysis of hydrolytic groups, reaction of hydroxyl groups on the substrate surface with silanol groups, and formation of siloxane bonds based on condensation reactions of silanol groups.

[0618] After surface treatment, compounds that are part of the surface treatment layer and 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.

[0619] Example

[0620] The following examples illustrate the invention in more detail, but the invention is not limited to these examples.

[0621] [Compound (A)]

[0622] <Synthesis of Compound (A1)>

[0623] THF (tetrahydrofuran, 30 mL), cesium fluoride (0.80 g), and bis(pentafluorophenyl) carbonate (7.4 g) were added to 3.0 g of 10-undecynic acid. The mixture was stirred at 25 °C for 16 hours to obtain a reaction solution. Water and hexane were added to the reaction solution to extract the organic layer. The solvent and low-boiling components were removed by vacuum distillation. Rapid column chromatography using silica gel (developing solvent: hexane / ethyl acetate) was then performed to obtain 3.5 g of compound (A1). The structure of compound (A1) was confirmed by the following NMR data.

[0624] [Chemistry 44]

[0625]

[0626] 1 H-NMR (400MHz, CDCl3): δ2.66 (t, J=7.4Hz, 2H), 2.19 (td, J=7.0, 2.7Hz, 2H), 1.99-1.23 (m, 13H).

[0627] <Synthesis of Compound (A2)>

[0628] THF (101g) was added to hexamethylcyclotrisiloxane (76g) and stirred until dissolved. A solution containing lithium salt of trimethylsilanol (5.1g) suspended in THF (20g) was then added, and the mixture was stirred at 25°C for 2 hours. Next, dichlorodimethylsilane (10.5g) was added, and the mixture was stirred at 25°C for 1 hour. After extraction with hexane and water, the solvent and low-boiling components were removed by vacuum distillation. The solution was then subjected to rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) to obtain 25g of compound (A2).

[0629] In compound (A2), the average value of ma is 17. The structure of compound (A2) was confirmed by the following NMR data.

[0630] [Chemistry 45]

[0631]

[0632] 1 H-NMR (400MHz, CDCl3): δ4.63 (hept, J=2.8Hz, 1H), 0.21-0.08 (m, 6H), 0.17-0.07 (m, 111H).

[0633] <Synthesis of Compounds (A3) and (A4)>

[0634] Dichloromethane (20 g) and compound (A2) (13 g) were added to compound (A1) (3.5 g) and stirred until homogeneous. Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added, and the mixture was stirred at 25 °C for 2 hours. After removing the solvent and low-boiling components by vacuum distillation, rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 2.5 g of compound (A3) and 0.8 g of compound (A4). The average ma value for compound (A3) was 17. Similarly, the average ma value for compound (A4) was 17. The structures of compounds (A3) and (A4) were confirmed by the following NMR data.

[0635] [Chemistry 46]

[0636]

[0637] 1 H-NMR (400MHz, CDCl3): δ6.03 (dt,J=18.6,6.2Hz,1H), 5.51 (dt,J=18.6,1.5Hz,1H), 2.56 (t,J=7.4Hz,2H), 2.11-1.00 (m,14H), 0.22-0.20 (m,111H).

[0638] [Chemistry 47]

[0639]

[0640] 1 H-NMR (400MHz, CDCl3): δ5.50-5.26 (m, 2H), 2.56 (t, J=7.5Hz, 2H), 2.12-0.90 (m, 14H), 0.22-0.20 (m, 111H).

[0641] <Synthesis of Compound (A5)>

[0642] 11-Bromo-1-undecene (11.8 g), potassium carbonate (11.2 g), and dimethylformamide (50 g) were added to methyl cyanoacetate (2.1 g), and the mixture was stirred overnight at 85 °C. After cooling to 25 °C, hydrochloric acid aqueous solution was added, and the mixture was extracted with dichloromethane. The solvent was removed by distillation, yielding 9.6 g of the following compound (A51). The structure of compound (A51) was confirmed by the following NMR data.

[0643] [Chemistry 48]

[0644]

[0645] 1 H-NMR (400MHz, CDCl3): δ5.92-5.74 (m, 2H), 5.13-4.90 (m, 4H), 3.80 (s, 3H), 2.20-1.90 (m, 4H), 1.90-1.00 (m, 32H).

[0646] Dimethyl sulfoxide (30 g) was added to compound (A51) (9.5 g), and after stirring, water (5 g) and lithium chloride (3.2 g) were added. The mixture was heated to 180 °C and stirred overnight. After cooling to 25 °C, it was extracted with dichloromethane, the solvent was removed by distillation, and rapid column chromatography using silica gel (developing solvent: ethyl acetate / hexane) was performed to obtain compound (A52) 7.4 g. The structure of compound (A52) was confirmed by the following NMR data.

[0647] [Chemistry 49]

[0648]

[0649] 1 H-NMR (400MHz, CDCl3): δ5.92-5.74 (m, 2H), 5.13-4.90 (m, 4H), 2.62-2.41 (m, 1H), 2.20-1.95 (m, 4H), 1.90-1.00 (m, 32H).

[0650] Compound (A52) (5.4 g) was dissolved in THF and cooled to 0°C. A THF solution of lithium aluminum hydride (27 mL, 27 mmol) was added and stirred. Water and a 15% (w / w) aqueous sodium hydroxide solution were added, and the mixture was stirred at 25°C and diluted with dichloromethane. After filtration, the solvent was removed by distillation, and the solution was subjected to rapid column chromatography using silica gel (developing solvent: methanol) to obtain 4.9 g of compound (A5). The structure of compound (A5) was confirmed by the following NMR data.

[0651] [Transformation 50]

[0652]

[0653] 1 H-NMR (400MHz, CDCl3): δ5.92-5.74 (m, 2H), 5.13-4.90 (m, 4H), 2.75-2.55 (m, 2H), 2.20-1.95 (m, 4H), 1.90-1.00 (m, 33H).

[0654] <Synthesis of Compound (A6)>

[0655] Dichloromethane (10 g) was added to compound (A3) (1.0 g) and homogenized, followed by compound (A5) (0.42 g). The mixture was stirred at 25 °C for 12 hours. After removing the solvent and low-boiling components by distillation, rapid column chromatography using silica gel (developing solvent: hexane / ethyl acetate) was performed to obtain compound (A6) 0.80 g. The average ma value of compound (A6) was 17. The structure of compound (A6) was confirmed by the following NMR data.

[0656] [Chemistry 51]

[0657]

[0658] 1 H-NMR (400MHz, CDCl3): δ6.14-4.65 (m, 9H), 3.11 (t, J=6.0Hz, 2H), 2.30-0.93 (m, 53H), 0.22-0.20 (m, 111H).

[0659] <Synthesis of Compound (A)>

[0660] Dichloromethane (10 g) was added to compound (A6) (0.80 g) and homogenized. Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.20 g) were added, and the mixture was stirred at 50 °C for 2 hours. The solvent was removed by vacuum distillation, yielding compound (A) 0.85 g. The average ma value of compound (A) was 17. The structure of compound (A) was confirmed by the following NMR data.

[0661] [Chemistry 52]

[0662]

[0663] 1H-NMR (400MHz, CDCl3): δ6.16-5.43 (m, 2H), 3.49 (s, 18H), 3.11 (t, J=6.0Hz, 2H), 2.32-0.31 (m, 61H), 0.22-0.20 (m, 111H).

[0664] [Compound (B)]

[0665] <Synthesis of Compound (B1)>

[0666] Dichloromethane (10 g) was added to compound (A4) (0.8 g) and homogenized, followed by compound (A5) (0.31 g). The mixture was stirred at 25 °C for 12 hours. After removing the solvent and low-boiling components by distillation, rapid column chromatography using silica gel (developing solvent: hexane / ethyl acetate) was performed to obtain compound (B1) 0.67 g. The average ma value of compound (B1) was 17. The structure of compound (B1) was confirmed by the following NMR data.

[0667] [Chemistry 53]

[0668]

[0669] 1 H-NMR (400MHz, CDCl3): δ5.91-4.68 (m, 9H), 3.04 (dd, J=6.0, 5.3Hz, 2H), 2.55-0.97 (m, 53H), 0.22-0.20 (m, 111H).

[0670] <Synthesis of Compound (B)>

[0671] Dichloromethane (10 g) was added to compound (B1) (0.67 g) and homogenized. Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.20 g) were added, and the mixture was stirred at 50 °C for 2 hours. The solvent and low-boiling components were removed by vacuum distillation to obtain compound (B) 0.71 g. The average ma value of compound (B) was 17. The structure of compound (B) was confirmed by the following NMR data.

[0672] [Chemistry 54]

[0673]

[0674] 1H-NMR (400MHz, CDCl3): δ5.91-4.99 (m, 2H), 3.49 (s, 18H), 3.04 (t, J=6.0Hz, 2H), 2.32-0.31 (m, 61H), 0.22-0.20 (m, 111H).

[0675] [Compound (C)]

[0676] <Synthesis of Compound (C1)>

[0677] THF (200 g) was added to 1-hexen-5-yne (8 g) and stirred until homogeneous, then cooled to 0 °C. Butyllithium (15% hexane solution, 1.6 mol / L) (50 mL) was then added, and the mixture was stirred at 0 °C for 30 min. Hexamethylcyclotrisiloxane (120 g) was then added, and the mixture was stirred at 25 °C for 16 h. Trimethylchlorosilane (20 g) was then added, and the mixture was stirred at 25 °C for 1 h. Water and hexane were added, the organic phase was extracted, and the solvent and low-boiling components were removed by distillation. Rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain compound (C1) 23 g. The average ma value of compound (C1) was 17. The structure of compound (C1) was confirmed by the following NMR data.

[0678] [Chemistry 55]

[0679]

[0680] 1 H-NMR (400MHz, CDCl3): δ5.92-5.57 (m, 1H), 5.24-4.83 (m, 2H), 2.46-1.72 (m, 4H), 0.14-0.03 (m, 111H).

[0681] <Synthesis of Compound (C)>

[0682] Dichloromethane (10 g) was added to compound (C1) (0.82 g) and homogenized. Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.07 g) were added, and the mixture was stirred at 50 °C for 2 hours. The solvent and low-boiling components were removed by vacuum distillation to obtain 0.85 g of the product, with compound (C) as the main component. The average ma value of compound (C) was 17. The structure of compound (C) was confirmed by the following NMR data.

[0683] [Chemistry 56]

[0684]

[0685] 1 H-NMR (400MHz, CDCl3): δ3.58 (s, 9H), 2.37-2.10 (m, 2H), 1.63-1.29 (m, 4H), 0.80-0.57 (m, 2H), 0.17-0.05 (m, 111H).

[0686] [Compound (D)]

[0687] <Synthesis of Compound (D1)>

[0688] Dichloromethane (20 g) and 1,1,1,3,3-pentamethyldisiloxane (2.3 g) were added to 2.5 g of 1-bromo-1-undecanyne and stirred until homogeneous. Then, a toluene solution of a platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added, and the mixture was stirred at 25 °C for 2 hours. The solvent and low-boiling components were removed by vacuum distillation, followed by rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) to obtain 3.0 g of compound (D1). The structure of compound (D1) was confirmed by the following NMR data.

[0689] [Chemistry 57]

[0690]

[0691] 1 H-NMR (400MHz, CDCl3): δ6.17-5.61 (m, 2H), 3.42 (t, J=4.7Hz, 2H), 2.15 (tdd, J=7.5, 6.2, 1.0Hz, 2H), 1.84-1.10 (m, 14H), 0.21--0.15 (m, 15H).

[0692] <Synthesis of Compound (D2)>

[0693] 10 g of 18-bromo-1-octadecene was mixed with 40 g of THF and 0.9 g of magnesium, and the mixture was stirred at 60 °C for 2 hours. The reaction mixture was filtered to give 50 g of compound (D2). The product was confirmed to have a concentration of 0.4 mol / L by titration with 1,10-phenanthroline.

[0694] [Chem.58]

[0695]

[0696] <Synthesis of Compound (D3)>

[0697] THF (10 g), compound (D2) (0.4 mol / L) (10 mL), and copper(II) chloride (0.05 g) were added to compound (D1) (1 g), and the mixture was stirred at 60 °C for 24 hours. Hydrochloric acid and hexane were added, and the organic phase was extracted. Low-boiling components were removed by vacuum distillation, followed by rapid column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / dichloromethane) to obtain compound (D3) 0.2 g. The structure of compound (D3) was confirmed by the following NMR data.

[0698] [Chemistry 59]

[0699]

[0700] 1 H-NMR (400MHz, CDCl3): δ6.15-4.68 (m, 5H), 2.28-1.84 (m, 4H), 1.54-1.12 (m, 46H), 0.21--0.15 (m, 15H).

[0701] <Synthesis of Compound (D)>

[0702] Dichloromethane (10 g) was added to compound (D3) (0.2 g) and homogenized. Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.3 g) were added, and the mixture was stirred at 50 °C for 2 hours. The solvent and low-boiling components were removed by vacuum distillation to obtain compound (D) 0.2 g. The structure of compound (D) was confirmed by the following NMR data.

[0703] [Transformation 60]

[0704]

[0705] 1 H-NMR (400MHz, CDCl3): δ6.21-5.30 (m, 2H), 3.58 (s, 9H), 2.15 (tdd, J=7.5, 6. 2, 1.0Hz, 2H), 1.59-1.02 (m, 50H), 0.65 (t, J=9.2Hz, 2H), 0.21--0.15 (m, 15H).

[0706] [Compound (E)]

[0707] <Synthesis of Compound (E1)>

[0708] Dichloromethane (20 g) and 1,1,3,3,5,5,7,7,9,9,11,11-dodecylhexasiloxane (3.0 g) were added to 1-bromo-1-undecanyne (7.0 g) and stirred until homogeneous. Then, a toluene solution of a platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) was added, and the mixture was stirred at 25 °C for 2 hours. The solvent and low-boiling components were removed by vacuum distillation, followed by rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) to obtain 1.2 g of compound (E1). The structure of compound (E1) was confirmed by the following NMR data.

[0709] [Chemistry 61]

[0710]

[0711] 1 H-NMR (400MHz, CDCl3): δ6.26-5.48 (m, 4H), 3.42 (t, J=4.7Hz, 4H), 2.15 (tdd, J=7.6, 6.3, 1.0Hz, 4H), 1.82-1.13 (m, 28H), 0.34--0.26 (m, 36H).

[0712] <Synthesis of Compound (E2)>

[0713] THF (10 g) and allyl magnesium chloride (11% THF solution, 1.0 mol / L) (10 mL) were added to compound (E1) (1 g), and the mixture was stirred at 60 °C for 24 hours. Hydrochloric acid and hexane were added, and the organic phase was extracted. Low-boiling components were removed by vacuum distillation, followed by rapid column chromatography using 10% silver nitrate silica gel (developing solvent: hexane / ethyl acetate) to obtain compound (E2) 0.7 g. The structure of compound (E2) was confirmed by the following NMR data.

[0714] [Chemistry 62]

[0715]

[0716] 1 H-NMR (400MHz, CDCl3): δ6.28-4.69 (m, 10H), 2.27-1.82 (m, 8H), 1.49-1.05 (m, 32H), 0.33--0.30 (m, 36H).

[0717] <Synthesis of Compound (E)>

[0718] Dichloromethane (10 g) was added to compound (E2) (0.4 g) and homogenized. Then, a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg), aniline (2.6 mg), and trimethoxysilane (0.5 g) were added, and the mixture was stirred at 35 °C for 2 hours. The solvent and low-boiling components were removed by vacuum distillation to obtain compound (E) 0.5 g. The structure of compound (E) was confirmed by the following NMR data.

[0719] [Chemistry 63]

[0720]

[0721] 1 H-NMR (400MHz, CDCl3): δ6.32-5.49 (m, 4H), 3.58 (s, 18H), 2.15 (tdd, J=7.6, 6. 3, 1.0Hz, 4H), 1.64-0.95 (m, 40H), 0.65 (t, J=9.2Hz, 4H), 0.31--0.20 (m, 36H).

[0722] [Compound (F)]

[0723] <Synthesis of Compound (F1)>

[0724] Dichloromethane (20 g) and Grubbs catalyst (trademark) M204 (0.1 g) were added to 5.0 g of 9-bromo-1-nonene, and the mixture was stirred at 35 °C for 24 hours. After removing the solvent and low-boiling components by vacuum distillation, rapid column chromatography using silica gel (developing solvent: hexane / dichloromethane) was performed to obtain 2.5 g of compound (F1). The structure of compound (F1) was confirmed by the following NMR data.

[0725] [Chemistry 64]

[0726]

[0727] 1 H-NMR (400MHz, CDCl3): δ5.50-5.21 (m, 2H), 3.41 (t, J=6.9Hz, 4H), 2.09-1.70 (m, 8H), 1.53-1.00 (m, 16H).

[0728] <Synthesis of Compound (F2)>

[0729] THF (10 g) and allyl magnesium chloride (11% THF solution, 1.0 mol / L) (10 mL) were added to compound (F1) (2 g), and the mixture was stirred at 60 °C for 24 hours. Hydrochloric acid and hexane were added, and the organic phase was extracted. Low-boiling components were removed by vacuum distillation, followed by rapid column chromatography using silica gel (developing solvent: hexane / ethyl acetate) to obtain compound (F2) 1.2 g. The structure of compound (F2) was confirmed by the following NMR data.

[0730] [Chemistry 65]

[0731]

[0732] 1 H-NMR (400MHz, CDCl3): δ5.81 (ddt, J=16.9, 10.2, 6.7Hz, 2H), 5.48-5.26 (m, 2H), 5.09-4.79 (m, 4H), 2.19-1.74 (m, 8H), 1.48-0.98 (m, 24H).

[0733] <Synthesis of Compound (F)>

[0734] Dichloromethane (10 g), trimethoxysilane (1.0 g), and 1,1,1,3,3-pentamethyldisiloxane (1.0 g) were added to compound (F2) (1.2 g) and homogenized. Then, a toluene solution of a platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass, 4.1 mg) and aniline (2.6 mg) were added, and the mixture was stirred at 35 °C for 3 hours. The solvent and low-boiling components were removed by vacuum distillation, followed by rapid column chromatography using silica gel (developing solvent: hexane / ethyl acetate), yielding compound (F) 0.5 g. The structure of compound (F) was confirmed by the following NMR data.

[0735] [Chemistry 66]

[0736]

[0737] 1 H-NMR (400MHz, CDCl3): δ5.51-5.17 (m, 2H), 3.57 (s, 9H), 2.01 (D, J=5.9Hz, 4H), 1 .48-1.03 (m, 32H), 0.75-0.58 (m, 2H), 0.50 (t, J=7.4Hz, 2H), 0.31--0.20 (m, 15H).

[0738] [Compound (Z)]

[0739] Compound (Z) was synthesized with reference to Example 1 described in International Publication No. 2023 / 017830.

[0740] It should be noted that compound (Z) is a compound that does not belong to either the compound shown in formula (1-1) or the compound shown in formula (1-2). The (SiMe2-O-) in compound (Z) 17 The average value is 17.

[0741] [Chemistry 67]

[0742]

[0743] [Item crafting]

[0744] Articles of Examples 1-7 were manufactured by surface-treating a substrate using compounds (A), (B), (C), (D), (E), (F), and (Z) described above. A dry coating method was used as the surface treatment method. Chemically strengthened glass was used as the substrate.

[0745] Dry coating method

[0746] Dry coating was performed using a vacuum evaporation apparatus (product name "VTR-350M", manufactured by ULVAC). A 20% by mass ethyl acetate solution (0.5 g) of each compound was filled into a molybdenum boat within the vacuum evaporation apparatus, and the pressure within the apparatus was set to 1 × 10⁻⁶. -3 Exhausting was performed using a method below Pa. The boat was heated at a heating rate of 10°C / min or less. When the evaporation rate, measured using a quartz oscillating film thickness gauge, exceeded 1 nm / s, the baffle was opened to begin film deposition on the substrate surface. The baffle was closed when the film thickness reached approximately 50 nm, ending film deposition on the substrate surface. The substrate with the deposited compound was then heated at 200°C for 30 minutes to obtain an article with a surface treatment layer on the substrate surface.

[0747] [evaluate]

[0748] The water repellency and abrasion resistance of items obtained by dry coating were evaluated. The evaluation method is as follows.

[0749] Water repellency

[0750] Approximately 2 μL of distilled water was added to the surface treatment layer of the article, and the initial water contact angle was measured using a contact angle measuring device (product name "DM-500", manufactured by Kyowa Interface Science Co., Ltd.). The average of the water contact angles measured at 5 points on the surface treatment layer was used as the initial water contact angle in the following evaluation. It should be noted that the water contact angle was calculated using the 2θ method. The evaluation criteria are as follows. A represents a level that is practically problem-free.

[0751] A: The initial water contact angle is above 105°.

[0752] B: The initial water contact angle is less than 105°.

[0753] <Abrasion Resistance>

[0754] For the surface treatment layer of the item, according to JIS L0849:2013 (corresponding to ISO: 105-X12:2001), a reciprocating traverse testing machine (manufactured by KNENTACORPORATION) was used to reciprocate steel wool Bonstar (#0000) 10,000 times at a pressure of 98.07 kPa and a speed of 320 cm / min. The water contact angle after the friction test was then measured. The method for measuring the water contact angle after the friction test is the same as the method for measuring the initial water contact angle in the above-mentioned evaluation method for water repellency. The average value of the water contact angles measured at 5 points on the surface treatment layer after the friction test is used as the water contact angle after the friction test in the following evaluation. Abrasion resistance is evaluated based on the reduction in the water contact angle from the friction test. The smaller the reduction in the water contact angle, the better the abrasion resistance. The evaluation criteria are as follows. A and B represent levels that are practically problem-free.

[0755] The decrease in water contact angle = (initial water contact angle) - (water contact angle after friction test)

[0756] A: The decrease in water contact angle is less than 1.5°.

[0757] B: The reduction in water contact angle is greater than 1.5° and less than 2.0°.

[0758] C: The reduction in water contact angle is greater than 2.0° and less than 4.0°.

[0759] D: The reduction in water contact angle is 4.0° or more.

[0760] The contents of the compounds used in each example and the evaluation results are shown in Table 1.

[0761] In Table 1, L 1 L 2 Columns A and B represent the corresponding functional groups. Additionally, "-A-(Si(R)" indicates... n L 3-n ) q "In the expression (1-1), -A-(Si(R))" n L 3-n ) q The group shown.

[0762] Examples 1-6 are examples, and Example 7 is a comparative example.

[0763] [Table 1]

[0764]

[0765] As shown in Table 1, it can be seen that the compounds of Examples 1 to 6 are able to form a surface treatment layer with excellent wear resistance compared to the compound of Example 7.

[0766] Furthermore, based on the comparison of Examples 1-6, it can be seen that in L 2 When the value is -CH=CH- or -C≡C-, the wear resistance is even better.

[0767] Industrial availability

[0768] The compounds of this invention are useful as surface treatment agents. For example, they can be used as substrates in display devices such as touch panel displays, optical components, semiconductor components, building materials, automotive components, and nanoimprint technology. Furthermore, they can be used in the bodies, windows (front, side, and rear windows), mirrors, and bumpers of transportation equipment such as trams, automobiles, ships, and aircraft. Moreover, they can be used in outdoor items such as building exteriors, 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 perimeter components; chandeliers, ceramics such as tiles; artificial marble, air conditioners, and various indoor equipment. Furthermore, they can be used as antifouling treatments for jigs, interior walls, and piping in factories. Additionally, they can be used in goggles, eyeglasses, helmets, marbles, fibers, umbrellas, toys, and soccer balls. Finally, they can be used as anti-adhesion agents in various packaging materials such as food packaging materials, cosmetic packaging materials, and the interior of jugs. In addition, surface treatment agents can be used in medical devices 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.

[0769] This application claims priority based on Japanese Patent Application No. 2023-110542, filed on July 5, 2023, the entire disclosure of which is incorporated herein by reference.

Claims

1. The compound represented by formula (1-1) or formula (1-2) below, TO- (Si) (R) 2 )2-O) ma -Si(R 2 )2-L 1 -L 2 -A- (Si (R)) n L 3-n ) q (1-1) (IT 3-n (R) n And) q Al 2 -IT 1 -(And(R) 2 )2-O) mb -And (R) 2 )2-L 1 -IT 2 -A- (And (R)) n IT 3-n ) q (1-2) T is (R) 1 ) 3Si-, monovalent cyclic polysiloxane residues or monovalent cage-like polysiloxane residues, R 1 Each is independently a hydrocarbon group or a trialkylsilyloxy group. R 2 Each is an independent hydrocarbon group. L 1 It is a single bond or a divalent linker. L 2 For -CH=CH-, -C≡C-, or -C(=CH2)-, A is a single bond or a (q+1) valence linker. R are each an independent hydrocarbon group. L can be a hydrolyzable group, a group with a hydrolyzable group, or a hydroxyl group, each independently. ma is a number greater than or equal to 0. mb is a number greater than or equal to 1. n are independent integers from 0 to 2. Each q is an integer greater than or equal to 1.

2. The compound according to claim 1, wherein, In equations (1-1) and (1-2), -A-(Si(R)) n L 3-n ) q The group shown is the group represented by formula (3-1A). -Q a -X 31 (-Q b -Si(R) n L 3-n ) h (-R 31 ) i (3-1A) Q a It is a single bond or a divalent linker. X 31 It can be a single bond, an alkylene group, a nitrogen atom, a carbon atom, a silicon atom, an organopolysiloxane residue with a valence of 2 to 8, or a cyclic group with a valence of (h+i+1). Q b It is a single bond or a divalent linker. R are each an independent hydrocarbon group. L can be a hydrolyzable group, a group with a hydrolyzable group, or a hydroxyl group, each independently. R 31 It can be a hydrogen atom, a hydroxyl group, or an alkyl group. n is an integer between 0 and 2. X 31 When the bond is a single bond or an alkylene group, h is 1 and i is 0. 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. 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. X 31 When the residues are organopolysiloxanes with valences 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. X 31 When the group is a ring 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.

3. The compound according to claim 1, wherein, L 1 It is a single bond or an alkylene group.

4. The compound according to claim 1, wherein, L 1 It is a single key.

5. The compound according to claim 1, wherein, ma and mb are each an independent number from 2 to 600.

6. The compound according to claim 1, wherein, q is an integer from 1 to 4.

7. A composition comprising the compound of any one of claims 1 to 6, and comprising a liquid medium.

8. A surface treatment agent comprising the compound according to any one of claims 1 to 6.

9. A surface treatment agent comprising the compound of any one of claims 1 to 6, and comprising a liquid medium.

10. 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 the surface-treated agent of claim 8.

11. An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent of claim 8.

12. The article according to claim 11, wherein it is an optical component.

13. The article of claim 11, wherein it is a display or a touch panel.

14. A method for manufacturing an article, wherein, By using the surface treatment agent of claim 9 to surface treat a substrate, an article having a surface treatment layer formed on the substrate is manufactured.

15. An article comprising a substrate and a surface treatment layer disposed on the substrate and surface-treated with the surface treatment agent of claim 9.

16. The article according to claim 15, wherein it is an optical component.

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

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